KR102806088B1 - Organometallic compound and organic light emitting device including the same - Google Patents

Abstract

상기 화학식 1 중 Y₂, 고리 CY₂, R₁ 내지 R₈, R₂₀, A₁ 내지 A₇ 및 d2에 대한 설명은 각각 본 명세서에 기재된 바를 참조한다. An organometallic compound represented by the following chemical formula 1 and an organic light-emitting device including the same are provided:
<Chemical Formula 1>

For descriptions of Y ₂ , ring CY ₂ , R ₁ to R ₈ , R ₂₀ , A ₁ to A ₇ and d2 in the above chemical formula 1, refer to those described in the present specification, respectively.

Description

Organometallic compound and organic light emitting device including the same {Organometallic compound and organic light emitting device including the same}

Organometallic compounds, organic light-emitting devices comprising the same, and diagnostic compositions comprising the same are provided.

Organic light emitting devices are self-luminous devices that have excellent viewing angle, response time, brightness, driving voltage, and response speed, and can be multi-colored.

According to an example, an organic light-emitting device may include an anode, a cathode, and an organic layer disposed between the anode and the cathode and including a light-emitting layer. A hole transport region may be provided between the anode and the light-emitting layer, and an electron transport region may be provided between the light-emitting layer and the cathode. Holes injected from the anode move to the light-emitting layer via the hole transport region, and electrons injected from the cathode move to the light-emitting layer via the electron transport region. The holes and electrons recombine in the light-emitting layer region to generate excitons. Light is generated when the excitons change from an excited state to a ground state.

Meanwhile, luminescent compounds, such as phosphorescent compounds, can also be used for monitoring, sensing, and detection of biological materials such as various cells and proteins.

The present invention provides a novel organometallic compound, an organic light-emitting device employing the same, and a diagnostic composition employing the same.

According to one aspect, an organometallic compound represented by the following chemical formula 1 is provided:

<Chemical formula 1>

In the above chemical formula 1,

Y ₂ is C,

Ring CY ₂ is a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group,

R ₁ to R ₈ , R ₂₀ and A ₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q 4 )(Q ₅ ), -B(Q ₆ )(Q _{7 )} , -P(=O)(Q ₈ )(Q ₉ ), or -P(Q ₈ )(Q ₉ ),

d2 is an integer from 0 to 10, and when d2 is 2 or greater, R ₂₀ of 2 or greater are the same or different from each other,

At least one of R ₁ to R ₈ and R ₂₀ comprises at least one fluoro group (-F),

A ₁ to A ₆ are each independently a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted A monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group,

Two or more of R ₁ to R ₈ may optionally be combined with each other to form a C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _1a or a C ₁ -C ₃₀ heterocyclic group substituted or unsubstituted with at least one R _1a ,

Two or more of d2 R ₂₀ may optionally be combined with each other to form a C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _1a or a C ₁ -C ₃₀ heterocyclic group substituted or unsubstituted with at least one R _1a ,

Two or more of A ₁ to A ₇ may optionally be combined with each other to form a C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _1a or a _{C 1} -C ₃₀ heterocyclic group substituted or unsubstituted with at least one R 1a,

For the description of the above R _1a , refer to the description of the above A ₇ ,

The substituents of the substituted C ₁ -C ₆₀ alkyl group, the substituted C ₂ -C ₆₀ alkenyl group, the substituted C ₂ -C ₆₀ alkynyl group, the substituted C ₁ -C ₆₀ alkoxy group, the substituted C ₃ -C ₁₀ cycloalkyl group, the substituted C ₁ -C ₁₀ heterocycloalkyl group, the substituted C ₃ -C ₁₀ cycloalkenyl group, the substituted C ₁ -C ₁₀ heterocycloalkenyl group, the substituted C ₆ -C ₆₀ aryl group, the substituted C ₆ -C ₆₀ aryloxy group, the substituted C ₆ -C ₆₀ arylthio group, the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic heterocondensed polycyclic group are,

deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, or a C ₁ -C ₆₀ alkoxy group;

deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, A C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C _{2 -C 60 alkynyl} group or a C _{1 -C 60} alkoxy group substituted with a monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q _{14 )(Q 15 )} , -Ge(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q _{17 )} , -P(=O)(Q ₁₈ )(Q ₁₉ ), -P(Q _{18 )} (Q _{19 )} , or any combination thereof;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C A C 3 -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C 1 -C 10 cycloalkyl group, a C 6 -C 60 aryloxy group, a C 6 _-C 60 arylthio group, a C 1 _{-C 60} heteroaryl group, a monovalent non-aromatic condensed polycyclic group, _a monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q _{23 )} (Q ₂₄ )(Q ₂₅ ), -Ge(Q ₂₃ )(Q ₂₄ )(Q _{25 ), -B(Q 26 )} (Q ₂₇ ), -P(=O)(Q ₂₈ )(Q _{29 )} , -P(Q _{28 )} (Q 29 ₎ , or any combination thereof, _{unsubstituted} or substituted with A heterocycloalkenyl group, a C ₆ -C ₆₀ aryl group, a C ₆ -C ₆₀ aryloxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group or a monovalent non-aromatic heterocondensed polycyclic group;

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -Ge(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ), -P(=O)(Q ₃₈ )(Q ₃₉ ) or -P(Q ₃₈ )(Q ₃₉ ); or

Any combination of these;

And,

The above Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C ₁ -C ₆₀ alkyl group unsubstituted or substituted with deuterium, a C _{1 -C 60} alkyl group, a C 6 -C ₆₀ aryl group, or any combination thereof; a C ₁ -C ₆₀ alkenyl group; a C ₂ -C ₆₀ alkynyl group; a C ₁ -C ₆₀ alkoxy group; a C ₃ -C ₁₀ cycloalkyl group; a C ₁ -C ₁₀ heterocycloalkyl group; A C ₃ -C ₁₀ cycloalkenyl group; a C ₁ -C ₁₀ heterocycloalkenyl group; a C ₆ -C ₆₀ aryl group unsubstituted or substituted with deuterium, a C ₁ -C ₆₀ alkyl group, a C ₆ -C ₆₀ aryl group, or any combination thereof; a C ₆ -C ₆₀ aryloxy group; a C ₆ -C ₆₀ arylthio group; a C ₁ -C ₆₀ heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.

According to another aspect, an organic light-emitting device is provided, comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, the organic layer including a light-emitting layer; wherein the organic layer includes at least one of the organometallic compounds.

The organometallic compound included in the emitting layer among the above organic layers can act as a dopant.

According to another aspect, a diagnostic composition is provided, comprising at least one organometallic compound represented by the chemical formula 1.

The above organometallic compound has excellent electrical properties and stability, so that an electronic device employing the organometallic compound, for example, an organic light-emitting device, can have an improved driving voltage, an improved external quantum efficiency, an improved roll-off ratio, an improved lifespan, and a relatively narrow full width at half maximum (FWHM) of an emission peak of an EL spectrum. In addition, since the organometallic compound has excellent phosphorescence characteristics, a diagnostic composition having high diagnostic efficiency can be provided by utilizing the same.

Figure 1 is a cross-sectional view schematically illustrating an organic light-emitting device according to one embodiment.

The above organometallic compound is represented by the following chemical formula 1:

<Chemical formula 1>

In the above chemical formula 1, Y ₂ can be C.

In the above chemical formula 1, ring CY ₂ may be a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group.

For example, in the chemical formula 1, ring CY ₂ is i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, or v) a condensed ring in which one or more first rings and one or more second rings are condensed with each other.

The above first ring is a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazacilole group or a triazacilole group,

The above second ring may be an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane group (norbornane group), a bicyclo[2.2.2]octane group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group or a triazine group.

According to one embodiment, the ring CY ₂ in the chemical formula 1 is selected from the group consisting of a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, a pyrrole group, a cyclopentadiene group, a silole group, a borole group, a phosphole group, a selenophene group, a zero mole group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzozermol group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, a dibenzosilole group, and a dibenzoborole. Group, dibenzophosphole group, dibenzoselenophene group, dibenzozermol group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzosilole group, azabenzoborole group, azabenzophosphole group, azabenzoselenophene group, azabenzozermol group, azadibenzothiophene group, azadibenzofuran group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzoborole group, azadibenzophosphole group, azadibenzoselenophene group, azadibenzozermol group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one Group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, It can be an adamantane group, a norbornane group, or a norbornene group.

According to another embodiment, the ring CY ₂ can be a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, a pyrrole group, a cyclopentadiene group, a silole group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, or a dibenzosilole group.

In the above chemical formula 1, R ₁ to R ₈ , R ₂₀ and A ₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted Or an unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q 4 )(Q ₅ ), -B(Q ₆ )(Q _{7 )} , -P(=O)(Q ₈ )(Q ₉ ), or -P(Q ₈ )(Q ₉ ). The description of the above Q ₁ to Q ₉ refers to the description in this specification, respectively.

According to one embodiment, R ₂₀ in the chemical formula 1 may not include a fluoro group (-F) and a cyano group. For example, R ₂₀ may be any group that does not include a fluoro group (-F) and a cyano group.

For example, in the chemical formula 1, R ₁ to R ₈ , R ₂₀ and A ₇ are independently of each other,

hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, -SF ₅ , a C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a deuterium-containing C ₁ -C ₂₀ alkyl group, a fluorinated C ₁ -C ₂₀ alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, adamantanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, Bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group(norbornanyl group), bicyclo[2.2.2]octyl group, (C ₁ -C ₂₀ alkyl)cyclopentyl group, (C ₁ -C ₂₀ alkyl)cyclohexyl group, (C ₁ -C ₂₀ alkyl)cycloheptyl group, (C ₁ -C ₂₀ alkyl)cyclooctyl group, (C ₁ -C ₂₀ alkyl)adamantanyl group, (C ₁ -C ₂₀ alkyl)norbornenyl group, (C ₁ -C ₂₀ alkyl)cyclopentenyl group, (C ₁ -C ₂₀ alkyl)cyclohexenyl group, (C ₁ -C ₂₀ alkyl)cycloheptenyl group, (C ₁ -C ₂₀ alkyl)bicyclo[1.1.1]pentyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.1.1]hexyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.1]heptyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.2]octyl group, silolanyl group, phenyl group, (C ₁ -C ₂₀ alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl group, pyridinyl group, pyrimidinyl group, or a C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxy group substituted with any combination thereof;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a deuterium-containing C ₁ -C ₂₀ alkyl group, a fluorinated C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, adamantanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, Bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.2]octyl group, (C ₁ -C ₂₀ alkyl)cyclopentyl group, (C ₁ -C ₂₀ alkyl)cyclohexyl group, (C ₁ -C ₂₀ alkyl)cycloheptyl group, (C ₁ -C ₂₀ alkyl)cyclooctyl group, (C ₁ -C ₂₀ alkyl)adamantanyl group, (C ₁ -C ₂₀ alkyl)norbornenyl group, (C ₁ -C ₂₀ alkyl)cyclopentenyl group, (C ₁ -C ₂₀ alkyl)cyclohexenyl group, (C ₁ -C ₂₀ alkyl)cycloheptenyl group, (C ₁ -C ₂₀ (C ₁ -C ₂₀ alkyl)bicyclo[1.1.1]pentyl group, (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.1]heptyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.2]octyl group, cilolanyl group, phenyl group, (C ₁ -C ₂₀ alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, Isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, A cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, adamantanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a scylolanyl group, a phenyl group, a (C ₁ -C ₂₀ alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, which is unsubstituted or substituted with an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, or any combination thereof. Pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group; or

-N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ) or -P(Q ₈ )(Q ₉ );

And,

Q ₁ to Q ₉ are independent of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH 3 , _-CH 2 CD ₃ , -CH ₂ CD _{2 H} , -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H, -CHDCDH ₂ , -CHDCD ₃ , -CD ₂ CD ₃ , -CD ₂ CD ₂ H or -CD ₂ CDH ₂ ; or

an _n -propyl group, _an isopropyl group, an n -butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n -pentyl group, a tert -pentyl group, a neopentyl group, an isopentyl group, a sec -pentyl group, a 3 -pentyl group, a sec -isopentyl group, a phenyl group, a biphenyl group or a naphthyl group, which is unsubstituted or substituted with deuterium, a C1 -C20 alkyl group, a phenyl group, or any combination thereof;

may be. Here, the R ₂₀ may not include a fluoro group and a cyano group.

According to one embodiment, R ₁ to R ₈ , R ₂₀ and A ₇ in the formula 1 may independently be hydrogen, deuterium, -F, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, -Si(Q ₃ )(Q ₄ )(Q ₅ ), or -Ge(Q ₃ )(Q ₄ )(Q ₅ ). Here, R ₂₀ may not include a fluoro group and a cyano group.

According to another embodiment, R ₁ to R ₈ and A ₇ in the chemical formula 1 are independently from each other,

Hydrogen, deuterium, or -F;

A C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or any combination thereof, substituted or unsubstituted with deuterium, -F, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or a C ₁ -C ₁₀ heterocycloalkyl group; or

-Si(Q ₃ )(Q ₄ )(Q ₅ ), or -Ge(Q ₃ )(Q ₄ )(Q ₅ );

It could be.

According to another embodiment, R ₂₀ in the chemical formula 1 is

hydrogen, or deuterium;

A C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or any combination thereof, which is unsubstituted or substituted with deuterium, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or a C ₁ -C ₁₀ heterocycloalkyl group; or

-Si(Q ₃ )(Q ₄ )(Q ₅ ), or -Ge(Q ₃ )(Q ₄ )(Q ₅ );

It could be.

In the above chemical formula 1, d2 represents the number of R ₂₀ and can be an integer from 0 to 10. When d2 is 2 or more, 2 or more R ₂₀ can be the same as or different from each other. For example, d2 can be an integer from 0 to 6.

At least one of R ₁ to R ₈ and R ₂₀ in the above chemical formula 1 may include at least one fluoro group (-F).

For example, at least one of R ₁ to R ₈ in the chemical formula 1 (e.g., at least one of R ₂ to R ₈ , or at least one of R ₃ to R ₆ ) may include at least one fluoro group (-F).

As another example, at least one of R ₁ to R ₈ in the above formula 1 (e.g., at least one of R ₂ to R ₈ , or at least one of R ₃ to R ₆ ) can independently be any group including at least one fluoro group (-F).

According to one embodiment, at least one of R ₁ to R ₈ in the chemical formula 1 is independently,

Fluoro group (-F); or

A fluorinated C ₁ -C ₂₀ alkyl group, a fluorinated C ₃ -C ₁₀ cycloalkyl group, or a fluorinated C ₁ -C ₁₀ heterocycloalkyl group, which is unsubstituted or substituted with deuterium, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or any combination thereof;

It could be.

In the above chemical formula 1, A ₁ to A ₆ are each independently a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, It may be a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group.

For example, in the chemical formula 1, A ₁ to A ₆ are independently selected from each other,

C ₁ -C ₂₀ alkyl group or C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a deuterium-containing C ₁ -C ₂₀ alkyl group, a fluorinated C ₁ -C ₂₀ alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, adamantanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, Bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.2]octyl group, (C ₁ -C ₂₀ alkyl)cyclopentyl group, (C ₁ -C ₂₀ alkyl)cyclohexyl group, (C ₁ -C ₂₀ alkyl)cycloheptyl group, (C ₁ -C ₂₀ alkyl)cyclooctyl group, (C ₁ -C ₂₀ alkyl)adamantanyl group, (C ₁ -C ₂₀ alkyl)norbornenyl group, (C ₁ -C ₂₀ alkyl)cyclopentenyl group, (C ₁ -C ₂₀ alkyl)cyclohexenyl group, (C ₁ -C ₂₀ alkyl)cycloheptenyl group, (C ₁ -C ₂₀ alkyl)bicyclo[1.1.1]pentyl group, (C ₁ -C ₂₀ A C ₁ -C 20 alkyl group or a C 1 -C ₂₀ alkoxy group substituted with a (C ₁ -C ₂₀ alkyl)bicyclo[2.1.1]hexyl group, a (C 1 -C 20 alkyl)bicyclo[2.2.1]heptyl group, a (C ₁ -C ₂₀ alkyl)bicyclo[2.2.2]octyl group, a scylolanyl group, a phenyl group, a (C ₁ -C ₂₀ alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a _1,2,3,4 -tetrahydronaphthyl group, a pyridinyl group, a _pyrimidinyl group, or any combination thereof; or

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a deuterium-containing C ₁ -C ₂₀ alkyl group, a fluorinated C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, adamantanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, Bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.2]octyl group, (C ₁ -C ₂₀ alkyl)cyclopentyl group, (C ₁ -C ₂₀ alkyl)cyclohexyl group, (C ₁ -C ₂₀ alkyl)cycloheptyl group, (C ₁ -C ₂₀ alkyl)cyclooctyl group, (C ₁ -C ₂₀ alkyl)adamantanyl group, (C ₁ -C ₂₀ alkyl)norbornenyl group, (C ₁ -C ₂₀ alkyl)cyclopentenyl group, (C ₁ -C ₂₀ alkyl)cyclohexenyl group, (C ₁ -C ₂₀ alkyl)cycloheptenyl group, (C ₁ -C ₂₀ (C ₁ -C ₂₀ alkyl)bicyclo[1.1.1]pentyl group, (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.1]heptyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.2]octyl group, cilolanyl group, phenyl group, (C ₁ -C ₂₀ alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, Isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, A cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, adamantanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C ₁ -C ₂₀ alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, which is unsubstituted or substituted with an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, or any combination thereof. Chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group;

It could be.

According to one embodiment, A ₁ to A ₆ in the above formula 1 can be, independently, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, or a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group.

In another embodiment, A ₁ to A ₆ in the above formula 1 may independently be a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, or a C ₁ -C ₂₀ alkyl group, a C 3 -C 10 cycloalkyl group, or a C 1 -C 10 heterocycloalkyl group, which is unsubstituted or substituted with deuterium, -F, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or any combination thereof.

For example, in the chemical formula 1, R ₁ to R ₈ , R ₂₀ and A ₇ are each independently hydrogen, deuterium, -F, -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a group represented by one of the following chemical formulas 9-1 to 9-39 , a group in which at least one hydrogen of one of the following chemical formulas 9-1 to 9-39 is substituted with deuterium, a group in which at least one hydrogen of one of the following chemical formulas 9-1 to 9-39 is substituted with -F, a group represented by one of the following chemical formulas 9-201 to 9-233 , a group in which at least one hydrogen of one of the following chemical formulas 9-201 to 9-233 is substituted with deuterium, a group in which at least one hydrogen of one of the following chemical formulas 9-201 to 9-233 is substituted with -F, a group represented by one of the following chemical formulas 10-1 to A group represented by one of the following formulae 10-126, a group in which at least one hydrogen of one of the following formulae 10-1 to 10-126 is substituted with deuterium, a group in which at least one hydrogen of one of the following formulae 10-1 to 10-126 is substituted with -F, a group represented by one of the following formulae 10-201 to 10-343, a group in which at least one hydrogen of one of the following formulae 10-201 to 10-343 is substituted with deuterium, a group in which at least one hydrogen of one of the following formulae 10-201 to 10-343 is substituted with -F, -Si(Q ₃ )(Q ₄ )(Q ₅ ) or -Ge(Q ₃ )(Q ₄ )(Q ₅ ) (however, the description of Q ₃ to Q ₅ is referred to as described herein), and at least one of R ₁ to R ₈ (for example, at least one of R ₂ to R ₈ , Or at least one of R ₃ to R ₆ ) may be -F, -CF ₃ , -CF ₂ H, -CFH ₂ , a group in which at least one hydrogen of one of the following formulae 9-1 to 9-39 is substituted with -F, a group in which at least one hydrogen of one of the following formulae 9-201 to 9-233 is substituted with -F, a group in which at least one hydrogen of one of the following formulae 10-1 to 10-126 is substituted with -F, or a group in which at least one hydrogen of one of the following formulae 10-201 to 10-343 is substituted with -F.

As another example, in the chemical formula 1, R ₂₀ is hydrogen, deuterium, -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , a group represented by one of the following chemical formulas 9-1 to 9-39 , a group in which at least one hydrogen of one of the following chemical formulas 9-1 to 9-39 is substituted with deuterium, a group represented by one of the following chemical formulas 9-201 to 9-233 , a group in which at least one hydrogen of one of the following chemical formulas 9-201 to 9-233 is substituted with deuterium, a group represented by one of the following chemical formulas 10-1 to 10-126 , a group in which at least one hydrogen of one of the following chemical formulas 10-1 to 10-126 is substituted with deuterium, a group represented by one of the following chemical formulas 10-201 to 10-343 , a group in which at least one hydrogen of one of the following chemical formulas 10-201 to 10-343 is substituted with deuterium, -Si(Q ₃ )(Q ₄ )(Q ₅ ) or -Ge(Q ₃ )(Q ₄ )(Q ₅ ) (however, the description of Q ₃ to Q ₅ refers to the description in this specification, respectively).

As another example, in the chemical formula 1, A ₁ to A ₆ are each independently -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a group represented by one of the following chemical formulae 9-1 to 9-39, a group in which at least one hydrogen of one of the following chemical formulae 9-1 to 9-39 is substituted with deuterium, a group in which at least one hydrogen of one of the following chemical formulae 9-1 to 9-39 is substituted with -F, a group represented by one of the following chemical formulae 9-201 to 9-233, a group in which at least one hydrogen of one of the following chemical formulae 9-201 to 9-233 is substituted with deuterium, a group in which at least one hydrogen of one of the following chemical formulae 9-201 to 9-233 is substituted with -F, a group represented by one of the following chemical formulae 10-1 to 10-126, a group represented by one of the following chemical formulae 10-1 to A group in which at least one hydrogen of one of the following formulae 10-126 is replaced with deuterium, a group in which at least one hydrogen of one of the following formulae 10-1 to 10-126 is replaced with -F, a group represented by one of the following formulae 10-201 to 10-343, a group in which at least one hydrogen of one of the following formulae 10-201 to 10-343 is replaced with deuterium, or a group in which at least one hydrogen of one of the following formulae 10-201 to 10-343 is replaced with -F:

In the above chemical formulas 9-1 to 9-39, 9-201 to 9-233, 10-1 to 10-126 and 10-201 to 10-343, * represents a bonding site with a neighboring atom, Ph represents a phenyl group, TMS represents a trimethylsilyl group and TMG represents a trimethylgermyl group.

The above "group in which at least one hydrogen atom among chemical formulae 9-1 to 9-39 is replaced with deuterium" and "group in which at least one hydrogen atom among chemical formulae 9-201 to 9-233 is replaced with deuterium" may be, for example, groups represented by the following chemical formulae 9-501 to 9-514 and 9-601 to 9-635:

The above "group in which at least one hydrogen among chemical formulae 9-1 to 9-39 is substituted with -F" and "group in which at least one hydrogen among chemical formulae 9-201 to 9-233 is substituted with -F" may be, for example, groups represented by the following chemical formulae 9-701 to 9-710:

The above "group in which at least one hydrogen atom among chemical formulae 10-1 to 10-126 is replaced with deuterium" and "group in which at least one hydrogen atom among chemical formulae 10-201 to 10-343 is replaced with deuterium" may be, for example, a group represented by the following chemical formulae 10-501 to 10-553:

The above "group in which at least one hydrogen among chemical formulae 10-1 to 10-126 is substituted with -F" and "group in which at least one hydrogen among chemical formulae 10-201 to 10-343 is substituted with -F" may be, for example, a group represented by the following chemical formulae 10-601 to 10-615:

According to one embodiment, at least one of R ₂ to R ₈ of the chemical formula 1 (for example, one or two of R ₂ to R ₈ ) may include at least one fluoro group (-F).

According to another embodiment, in the chemical formula 1,

1) R ₂ contains at least one fluoro group (-F);

2) R ₃ contains at least one fluoro group (-F);

3) R ₄ contains at least one fluoro group (-F);

4) R ₅ contains at least one fluoro group (-F);

5) R ₆ contains at least one fluoro group (-F);

6) R ₇ contains at least one fluoro group (-F);

7) R ₈ contains at least one fluoro group (-F);

8) each of R ₄ and R ₅ contains at least one fluoro group (-F);

9) each of R ₄ and R ₆ contains at least one fluoro group (-F);

10) each of R ₅ and R ₆ contains at least one fluoro group (-F);

11) each of R ₃ and R ₄ comprises at least one fluoro group (-F); or

12) Each of R ₃ and R ₆ may contain at least one fluoro group (-F).

According to another embodiment, in the chemical formula 1,

One or two of R ₁ to R ₈ independently comprise at least one fluoro group (-F),

At least one of R ₁ to R ₈ may i) not contain a fluoro group (-F), and ii) not be hydrogen.

In another embodiment, R ₅ in the chemical formula 1 may not be hydrogen.

According to another embodiment, R ₂₀ in the formula 1 may be a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, or a C ₁ -C ₁₀ heterocycloalkyl group, which is unsubstituted or substituted with deuterium, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or any combination thereof.

According to another embodiment, R ₂₀ in the above formula 1 can be a C ₁ -C ₂₀ alkyl group which is unsubstituted or substituted with deuterium, a C ₁ -C ₂₀ alkyl group, or any combination thereof.

According to another embodiment, d2 in the chemical formula 1 may be 2.

According to another embodiment, R ₂₀ in the formula 1 is a C ₁ -C ₂₀ alkyl group which is unsubstituted or substituted with deuterium, a C ₁ -C ₂₀ alkyl group, or any combination thereof, and d2 can be 2.

According to another embodiment, the organometallic compound represented by the above formula 1 may contain at least one deuterium.

According to another embodiment, at least one of R ₁ to R ₈ of the chemical formula 1 may include at least one deuterium.

In another embodiment, at least one of the d2 R _20s of the formula 1 may comprise deuterium.

In another embodiment, at least one of d2 R ₂₀ in the formula 1 may be a deuterium-containing C ₁ -C ₂₀ alkyl group, a deuterium-containing C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or a deuterium-containing C ₁ -C ₁₀ heterocycloalkyl group, which is unsubstituted or substituted with a C 1 -C 20 alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or any combination thereof.

In the above chemical formula 1, 1) two or more of R ₁ to R ₈ may optionally be combined with each other to form a C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _1a or a C ₁ -C ₃₀ heterocyclic group substituted or unsubstituted with at least one R _1a , 2) two or more of d2 R ₂₀ may optionally be combined with each other to form a C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _1a or a _{C 1} -C ₃₀ heterocyclic group substituted or unsubstituted with at least one R 1a, 3) two or more of A ₁ to A ₇ may optionally be combined with each other to form a C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least _{one R 1a or} a C ₁ -C ₃₀ A heterocyclic group can be formed. Here, the description of R _1a refers to the description of A ₇ in this specification.

In the present specification, the C ₅ -C ₃₀ carbocyclic group refers to a saturated or unsaturated cyclic group having only 5 to 30 carbons as ring-forming atoms. The C ₅ -C ₃₀ carbocyclic group can be a monocyclic group or a polycyclic group. "(C ₅ -C ₃₀ carbocyclic group (substituted or unsubstituted with at least one R _1a )" means, for example, (substituted or unsubstituted with at least one R _1a ) adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane group (norbornane group), a bicyclo[2.2.2]octane group, a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, a silole group, It may contain fluorene groups, etc.

In the present specification, the C ₁ -C ₃₀ heterocyclic group refers to a saturated or unsaturated cyclic group having, in addition to 1 to 30 carbons as ring-forming atoms, at least one heteroatom selected from N, O, P, Si and S. The C ₁ -C ₃₀ heterocyclic group may be a monocyclic group or a polycyclic group. "C ₁ -C ₃₀ heterocyclic group (substituted or unsubstituted with at least one R _1a )" means, for example, a (substituted or unsubstituted with at least one R _1a ) thiophene group, a furan group, a pyrrole group, a silole group, a borole group, a phosphole group, a selenophene group, a zero mole group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzozermol group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzozermol group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide Group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzosilole group, azabenzoborole group, azabenzophosphole group, azabenzoselenophene group, azabenzozermole group, azadibenzothiophene group, azadibenzofuran group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzoborole group, azadibenzophosphole group, azadibenzoselenophene group, azadibenzozermole group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline It may include a group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, and the like.

As used herein, the term "C ₁ -C ₆₀ alkyl group" refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, a hexyl group, and the like. As used herein, the term "C ₁ -C ₆₀ alkylene group" refers to a divalent group having the same structure as the C ₁ -C ₆₀ alkyl group.

Examples of the C ₁ -C ₆₀ alkyl group, the C ₁ -C ₂₀ alkyl group and/or the C ₁ -C ₁₀ alkyl group in the present specification include a methyl group, an ethyl group, an n -propyl group, an isopropyl group, an n -butyl group, a sec -butyl group, an isobutyl group, a tert -butyl group, an n -pentyl group, a tert -pentyl group, a neopentyl group, an isopentyl group, a sec -pentyl group, a 3-pentyl group, a sec -isopentyl group, an n -hexyl group, an isohexyl group, a sec -hexyl group, a tert -hexyl group, an n -heptyl group, an isoheptyl group, a sec -heptyl group, a tert -heptyl group, an n -octyl group, an isooctyl group, a sec -octyl group, a tert -octyl group, an n -nonyl group, an isononyl group, a sec -nonyl group, a tert - a methyl group, an ethyl group, an n -propyl group, an isopropyl group, an n -butyl group, a sec -butyl group, an isobutyl group, a tert -butyl group, an n -pentyl group, a tert -pentyl group, a neopentyl group, an isopentyl group, a sec -pentyl group, a 3 -pentyl group, a sec -isopentyl group, an n -hexyl group, an isohexyl group, a sec -hexyl group, a tert -hexyl group, an n -heptyl group, an isoheptyl group, a sec -heptyl group, a tert -heptyl group, an n -octyl group, an isooctyl group, a sec -octyl group, a tert -octyl group, an n -nonyl group, an isononyl group, a sec -nonyl group, a tert -nonyl group, n -decyl group, isodecyl group, sec -decyl group or tert -decyl group may be included. For example, the above chemical formula 9-33 can be viewed as a branched C ₆ alkyl group, which is a tert-butyl group substituted with two methyl groups.

In the present specification, the C ₁ -C ₆₀ alkoxy group means a monovalent group having the chemical formula of -OA ₁₀₁ (wherein, A ₁₀₁ is the C ₁ -C ₆₀ alkyl group), and specific examples thereof include a methoxy group, an ethoxy group, an isopropyloxy group, and the like.

Examples of a C ₁ -C ₆₀ alkoxy group, a C ₁ -C ₂₀ alkoxy group or a C ₁ -C ₁₀ alkoxy group in the present specification may include a methoxy group, an ethoxy group, a propoxy group, a butoxy group or a pentoxy group.

As used herein, the term “C ₃ -C ₁₀ cycloalkyl group” refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and the like. As used herein, the term “C ₃ -C ₁₀ cycloalkylene group” refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkyl group.

Examples of the C ₃ -C ₁₀ cycloalkyl group in the present specification may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, adamantanyl, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group (norbornanyl), a bicyclo[2.2.2]octyl group, and the like.

As used herein, the C ₁ -C ₁₀ heterocycloalkyl group refers to a monovalent monocyclic group having 1 to 10 carbon atoms that contains at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and specific examples thereof include a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. As used herein, the C ₁ -C ₁₀ heterocycloalkylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkyl group.

Examples of the C ₁ -C ₁₀ heterocycloalkyl group in the present specification may include a silolanyl group, a silinanyl group, a tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, a tetrahydrothiophenyl group, and the like.

The term "deuterium-containing C ₁ -C ₆₀ alkyl group (or, deuterium-containing C ₁ -C ₂₀ alkyl group, deuterium-containing C ₂ -C ₂₀ alkyl group, etc.)" as used herein means a C ₁ -C ₆₀ alkyl group substituted with at least one deuterium atom (or, a C ₁ -C ₂₀ alkyl group substituted with at least one deuterium atom, a C ₂ -C ₂₀ alkyl group substituted with at least one deuterium atom, etc.). For example, "deuterium-containing C ₁ alkyl group (i.e., deuterium-containing methyl group)" includes -CD ₃ , -CD ₂ H, and -CDH ₂ .

The term "deuterium-containing C ₃ -C ₁₀ cycloalkyl group" used herein means a C ₃ -C ₁₀ cycloalkyl group substituted with at least one deuterium. Examples of the "deuterium-containing C ₃ -C ₁₀ cycloalkyl group" include, for example, the chemical formula 10-501, etc.

As used herein, the terms “fluorinated C ₁ -C ₆₀ alkyl group (or, fluorinated C ₁ -C ₂₀ alkyl group, etc.)”, “fluorinated C ₃ -C ₁₀ cycloalkyl group”, or “fluorinated C ₁ -C ₁₀ heterocycloalkyl group” mean a C ₁ -C ₆₀ alkyl group (or, C ₁ -C ₂₀ alkyl group, etc.), a C ₃ -C ₁₀ cycloalkyl group, and a C ₁ -C ₁₀ heterocycloalkyl group, each of which is substituted with at least one fluoro group (-F). For example, “fluorinated C ₁ alkyl group (i.e., fluorinated methyl group)” includes -CF ₃ , -CF ₂ H, and -CFH ₂ . The above "fluorinated C ₁ -C ₆₀ alkyl group (or, fluorinated C ₁ -C ₂₀ alkyl group, etc.)", "fluorinated C ₃ -C ₁₀ cycloalkyl group", or "fluorinated C ₁ -C ₁₀ heterocycloalkyl group" means i) a fully fluorinated C ₁ -C ₆₀ alkyl group (or, fully fluorinated C ₁ -C ₂₀ alkyl group, etc.), a fully fluorinated C ₃ -C ₁₀ cycloalkyl group, or a fully fluorinated C ₁ -C ₁₀ heterocycloalkyl group, wherein all hydrogens contained in each group are replaced by fluoro groups, or ii) a partially fluorinated C ₁ -C ₆₀ alkyl group (or, partially fluorinated C ₁ -C ₂₀ alkyl group, etc.), a partially fluorinated C ₃ -C ₁₀ A cycloalkyl group, or a partially fluorinated C ₁ -C ₁₀ heterocycloalkyl group.

As used herein, the term "(C ₁ -C ₂₀ alkyl) 'X'group" refers to an 'X' group substituted with at least one C ₁ -C ₂₀ alkyl group. For example, as used herein, the term "(C ₁ -C ₂₀ alkyl)C ₃ -C ₁₀ cycloalkyl group" refers to a C ₃ -C ₁₀ cycloalkyl group substituted with at least one C ₁ -C ₂₀ alkyl group, and the term "(C ₁ -C ₂₀ alkyl)phenyl group" refers to a phenyl group substituted with at least one C ₁ -C ₂₀ alkyl group. An example of a (C ₁ alkyl)phenyl group is a toluyl group.

As used herein, the term “C ₂ -C ₆₀ alkenyl group” refers to a structure having one or more carbon-carbon double bonds in the middle or terminal of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, a butenyl group, and the like. As used herein, the term “C ₂ -C ₆₀ alkenylene group” refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkenyl group.

As used herein, the term “C ₂ -C ₆₀ alkynyl group” refers to a structure including one or more carbon-carbon triple bonds in the middle or terminal of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethynyl group, a propynyl group, and the like. As used herein, the term “C ₂ -C ₆₀ alkynylene group” refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkynyl group.

As used herein, the term “C ₃ -C ₁₀ cycloalkenyl group” refers to a monovalent monocyclic group having 3 to 10 carbon atoms, having at least one carbon-carbon double bond in the ring, but having no aromaticity. Specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. As used herein, the term “C ₃ -C ₁₀ cycloalkenylene group” refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkenyl group.

As used herein, the C ₁ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms and including at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and having at least one double bond in the ring. Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. As used herein, the C ₁ -C ₁₀ heterocycloalkenylene group means a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

In the present specification, the C ₆ -C ₆₀ aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the C ₆ -C ₆₀ arylene group refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Specific examples of the C ₆ -C ₆₀ aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a chrysenyl group, and the like. When the C ₆ -C ₆₀ aryl group and the C ₆ -C ₆₀ arylene group include two or more rings, the two or more rings may be fused to each other.

As used herein, the term C ₇ -C ₆₀ alkylaryl group refers to a C ₆ -C ₆₀ aryl group substituted with at least one C ₁ -C ₆₀ alkyl group.

In the present specification, the C ₁ -C ₆₀ heteroaryl group means a monovalent group containing at least one heteroatom selected from N, O, P, Si and S as a ring-forming atom and having a cyclic aromatic system having 1 to 60 carbon atoms, and the C ₁ -C ₆₀ heteroarylene group means a divalent group containing at least one heteroatom selected from N, O, P, Si and S as a ring-forming atom and having a carbocyclic aromatic system having 1 to 60 carbon atoms. Specific examples of the C ₁ -C ₆₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and the like. When the above C ₁ -C ₆₀ heteroaryl group and C ₁ -C ₆₀ heteroarylene group include two or more rings, the two or more rings may be fused to each other.

As used herein, the term C ₂ -C ₆₀ alkylheteroaryl group refers to a C ₁ -C ₆₀ heteroaryl group substituted with at least one C ₁ -C ₆₀ alkyl group.

In the present specification, the C ₆ -C ₆₀ aryloxy group refers to -OA ₁₀₂ (wherein, A ₁₀₂ is the C ₆ -C ₆₀ aryl group), and the C ₆ -C ₆₀ arylthio group refers to -SA ₁₀₃ (wherein, A ₁₀₃ is the C ₆ -C ₆₀ aryl group).

In the present specification, a monovalent non-aromatic condensed polycyclic group means a monovalent group (for example, having 8 to 60 carbon atoms) in which two or more rings are condensed with each other, contain only carbon as a ring-forming atom, and have non-aromaticity as an entire molecule. Specific examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group, etc. In the present specification, a divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

In the present specification, a monovalent non-aromatic condensed heteropolycyclic group means a monovalent group (for example, having 1 to 60 carbon atoms) in which two or more rings are condensed with each other, and includes a heteroatom selected from N, O, P, Si and S in addition to carbon as a ring-forming atom, and the entire molecule has non-aromaticity. The monovalent non-aromatic condensed heteropolycyclic group includes a carbazolyl group, etc. The divalent non-aromatic condensed heteropolycyclic group in the present specification means a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

In the present specification, a substituted C ₅ -C ₃₀ carbocyclic group, a substituted C ₂ -C ₃₀ heterocyclic group, a substituted C ₁ -C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted C ₆ -C ₆₀ aryl group, a substituted C ₇ -C ₆₀ alkylaryl group, a substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, Substituents of a substituted C ₂ -C ₆₀ alkylheteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group and a substituted monovalent non-aromatic heterocondensed polycyclic group are,

deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, or a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₇ -C ₆₀ alkylaryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₂ -C ₆₀ alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -Ge(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q ₁₈ )(Q ₁₉ ), -P(Q ₁₈ )(Q ₁₉ ), or a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group or a C ₁ -C ₆₀ alkoxy group substituted with any combination thereof;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₇ -C A C ₃ -C ₁₀ cycloalkyl group, C 1 -C 10 , which is unsubstituted or substituted with _{a 60} alkylaryl group, a C ₆ -C ₆₀ aryloxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a C _{2 -C 60 alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, -N(Q 21 )(Q 22 ), -Si(Q 23 )(Q 24 ) ( Q 25 ) , -Ge} (Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q 27 ), -P(=O)(Q ₂₈ )(Q ₂₉ ), -P(Q _{28 )} (Q _{29 )} , or any combination thereof A heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group, a C ₆ -C ₆₀ aryl group, a C ₇ -C ₆₀ alkylaryl group, a C ₆ -C ₆₀ aryloxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a C ₂ -C ₆₀ alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group or a monovalent non-aromatic condensed heteropolycyclic group;

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -Ge(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ), -P(=O)(Q ₃₈ )(Q ₃₉ ), or -P(Q ₃₈ )(Q ₃₉ ); or

Any combination of these;

It could be.

In the present specification, Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ independently represent hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C ₁ -C ₆₀ alkyl group unsubstituted or substituted with deuterium, a C ₁ -C ₆₀ alkyl group, a C ₆ -C ₆₀ aryl group, or any combination thereof; a C ₁ -C ₆₀ alkenyl group; a C ₂ -C ₆₀ alkynyl group; a C ₁ -C ₆₀ alkoxy group; a C ₃ -C ₁₀ cycloalkyl group; a C ₁ -C ₁₀ heterocycloalkyl group; A C ₃ -C ₁₀ cycloalkenyl group; a C ₁ -C ₁₀ heterocycloalkenyl group; a C ₆ -C ₆₀ aryl group unsubstituted or substituted with deuterium, a C ₁ -C ₆₀ alkyl group, a C ₆ -C ₆₀ aryl group, or any combination thereof; a C ₆ -C ₆₀ aryloxy group; a C ₆ -C ₆₀ arylthio group; a C ₁ -C ₆₀ heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic heterocondensed polycyclic group.

For example, in the present specification, Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH 3 , _-CH 2 CD ₃ , -CH ₂ CD _{2 H} , -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H, -CHDCDH ₂ , -CHDCD ₃ , -CD ₂ CD ₃ , -CD ₂ CD ₂ H or -CD ₂ CDH ₂ ; or

an n- _propyl group, _an isopropyl group, an n -butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n -pentyl group, a tert -pentyl group, a neopentyl group, an isopentyl group, a sec -pentyl group, a 3 -pentyl group, a sec -isopentyl group, a phenyl group, a biphenyl group or a naphthyl group, which is unsubstituted or substituted with deuterium, a C 1 -C 10 alkyl group, a phenyl group, or any combination thereof;

It could be.

In this specification, "azaindole group, azabenzoborole group, azabenzophosphol group, azaindene group, azabenzosilole group, azabenzozermole group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborole group, azadibenzphosphol group, azafluorene group, azadibenzosilole group, azadibenzozermole group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group" are each, "indole group, benzoborole group, benzophosphol group, indene group, benzosilole group, benzozermole group, benzothiophene A heterocycle having the same backbone as a "group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzosilole group, dibenzozermol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group", but at least one of the carbons forming the ring is replaced with nitrogen.

로 표시된 그룹은 하기 화학식 CY1 내지 CY108 중 하나로 표시된 그룹일 수 있다:According to one embodiment, among the chemical formula 1

The group represented by may be a group represented by one of the following chemical formulas CY1 to CY108:

Among the chemical formulas CY1 to CY108 above,

T ₂ to T ₈ are independent of each other,

Fluoro group (-F); or

A fluorinated C ₁ -C ₂₀ alkyl group, a fluorinated C ₃ -C ₁₀ cycloalkyl group, or a fluorinated C ₁ -C ₁₀ heterocycloalkyl group, which is unsubstituted or substituted with deuterium, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or any combination thereof;

And,

For descriptions of R ₂ to R ₈ and R _1a , refer to those described in claim 1, respectively, except that R ₂ to R ₈ are not hydrogen,

* is the binding site with Ir in chemical formula 1,

*" is a bonding site with a neighboring atom in chemical formula 1.

For example, among the chemical formulas CY1 to CY108, R ₂ to R ₈ are independently selected from each other,

deuterium; or

A C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or any combination thereof, unsubstituted or substituted with deuterium, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or a C ₁ -C ₁₀ heterocycloalkyl group;

It could be.

로 표시된 그룹은 하기 화학식 A(1) 내지 A(7) 중 하나로 표시된 그룹일 수 있다:According to another embodiment, in the chemical formula 1

The group represented by may be a group represented by one of the following chemical formulae A(1) to A(7):

Among the above chemical formulas A(1) to A(7),

Y ₂ is C,

X ₂ is O, S, N(R ₂₅ ), C(R ₂₅ )(R ₂₆ ), or Si(R ₂₅ )(R ₂₆ ),

For descriptions of R ₉ to R ₁₂ and R ₂₁ to R ₂₆ , refer to the description of R ₂₀ in this specification, respectively.

*' is the binding site with Ir in chemical formula 1,

*" is a bonding site with a neighboring atom in chemical formula 1.

For example, in the above formula A(1), R ₉ and R ₁₁ can be, independently, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or a C _{1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, or a C 1 -C 10 heterocycloalkyl group, which are unsubstituted or substituted with deuterium, a C 1} -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or a C ₁ -C ₁₀ heterocycloalkyl group, or any combination thereof.

As another example, R ₉ and R ₁₁ in the above formula A(1) can independently be a C ₁ -C ₂₀ alkyl group which is unsubstituted or substituted with deuterium, a C ₁ -C ₂₀ alkyl group, or any combination thereof.

As another example, R ₁₀ and R ₁₂ in the above chemical formula A(1) can be, independently, hydrogen or deuterium.

As another example, R ₉ and R ₁₁ in the above chemical formula A(1) can be the same as each other.

As another example, R ₉ and R ₁₁ in the above chemical formula A(1) may be different from each other.

As another example, in the chemical formula A(1), R ₉ and R ₁₁ may be different from each other, and the number of carbons contained in R ₁₁ may be greater than the number of carbons contained in R ₉ .

As another example, i) at least one of R ₉ to R ₁₂ of the formula A(1), ii) one of R ₁₁ , R ₁₂ , R ₂₁ to R ₂₆ of the formulae A(2) and A(3), or any combination thereof, iii) one of R ₉ , R ₁₂ , R ₂₁ to R ₂₆ of the formulae A(4) and A(5), or any combination thereof, and iv) one of R 9 , R ₁₀ , R _{21 to R 26 of} the formulae A(6) and A(7), or any combination thereof, are independently a deuterium-containing C ₁ -C ₂₀ alkyl group, a deuterium-containing C 3 , which is unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or any combination thereof _. -C ₁₀ cycloalkyl group, or a deuterium-containing C ₁ -C ₁₀ heterocycloalkyl group.

As another example, at least one of R ₉ and R ₁₁ of the above formula A(1) (e.g., R ₉ and R ₁₁ of the formula A(1)) can independently be a deuterium-containing C ₁ -C ₂₀ alkyl group, a deuterium-containing C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or any combination thereof, which is unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, or a deuterium-containing C ₁ -C ₁₀ heterocycloalkyl group.

로 표시된 그룹은 하기 화학식 A(1) 또는 A(5)로 표시된 그룹일 수 있다.According to another embodiment, among the chemical formula 1

The group represented by may be a group represented by the following chemical formula A(1) or A(5).

Meanwhile, at least one of A ₁ to A ₆ in the chemical formula 1 may independently be a substituted or unsubstituted C ₂ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, or a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group.

For example, at least one of A ₁ to A ₃ in the chemical formula 1 and at least one of A ₄ to A ₆ may independently be a substituted or unsubstituted C ₂ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, or a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group.

Meanwhile, the number of carbon atoms included in the group represented by *-C(A ₁ )(A ₂ )(A ₃ ) in the chemical formula 1 may be 5 or more, and/or the number of carbon atoms included in the group represented by *-C(A ₄ )(A ₅ )(A ₆ ) in the chemical formula 1 may be 5 or more.

According to one embodiment, A ₁ to A ₃ of the groups represented by *-C(A ₁ )(A ₂ )(A ₃ ) in the above formula 1 can be combined with each other to form a C _{5 -C 30} carbocyclic group substituted or unsubstituted with at least one R _1a or a C ₁ -C ₃₀ heterocyclic group substituted or unsubstituted with at least one R 1a. That is, the group represented by *-C(A ₁ )(A ₂ )(A ₃ ) in the above chemical formula ₁ may be a C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _1a or a C ₁ -C ₃₀ heterocyclic group substituted or unsubstituted with at least one R _1a (for example, an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane group (norbornane group), a bicyclo[2.2.2]octane group, a cyclopentane group, a cyclohexane group, or a cyclohexene group, all of which are substituted or unsubstituted with at least one R 1a).

According to another embodiment, A ₄ to A ₆ of the group represented by *-C(A ₄ )(A ₅ )(A ₆ ) in the above formula 1 can be combined with each other to form a C _{5 -C 30} carbocyclic group substituted or unsubstituted with at least one R _1a or a C ₁ -C ₃₀ heterocyclic group substituted or unsubstituted with at least one R 1a. That is, the group represented by *-C(A ₄ )(A ₅ )(A ₆ ) in the above chemical formula ₁ may be a C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _1a or a C ₁ -C ₃₀ heterocyclic group substituted or unsubstituted with at least one R _1a (for example, an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane group (norbornane group), a bicyclo[2.2.2]octane group, a cyclopentane group, a cyclohexane group, or a cyclohexene group, all of which are substituted or unsubstituted with at least one R 1a).

According to another embodiment, A ₁ , A ₂ and A ₃ in the chemical formula 1 may independently be a substituted or unsubstituted C ₁ alkyl group (substituted or unsubstituted methyl group).

According to another embodiment, A ₁ , A ₂ and A ₃ in the above formula 1 may independently be a C ₁ alkyl group unsubstituted or substituted with deuterium, -F, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or any combination thereof.

For example, the organometallic compound may be, but is not limited to, at least one of the following compounds 1 to 16:

Among the organometallic compounds represented by the above chemical formula 1, 1) the ring CY ₁ (see chemical formula 1' below) is a condensed ring in which two benzene groups and one pyridine group are condensed with each other as shown in chemical formula 1, and 2) at least one of R ₁ to R ₈ and R ₂₀ of chemical formula 1 includes at least one fluoro group (-F). Accordingly, the transition dipole moment of the organometallic compound is improved, the conjugation length of the organometallic compound is relatively increased, and structural rigidity is increased, so that a non-luminescent transition can be reduced. Therefore, an electronic device employing the organometallic compound represented by the above chemical formula 1, for example, an organic light-emitting device, can have a high external quantum efficiency (EQE), and thus can have high luminous efficiency.

<Chemical Formula 1'>

In addition, in the above chemical formula 1, A ₁ to A ₆ are each independently a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ It may be a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group. That is, A ₁ to A ₆ in the above chemical formula 1 may have 1 or more carbons.

Although not limited by a specific theory, α-protons have chemical reactivity about 10 ⁵ times greater than β-protons, and thus α-protons can cause side reactions by generating various forms of intermediates during compound synthesis and/or storage. However, since A ₁ to A ₆ of the above chemical formula 1 are defined as described above, the carbon bonded to A ₁ to A ₆ in the above chemical formula 1 may not include α-protons, and thus the organometallic compound represented by the above chemical formula 1 has a stable chemical structure in which side reactions are minimized before/after synthesis, while at the same time, the interaction between organometallic compound molecules can be minimized during the operation of an electronic device (e.g., an organic light-emitting device) employing the same.

Furthermore, since the chemical formula 1 includes Ligand 2 which is structurally bulky and has strong electron-donating ability, the interaction between Ligand 2 and Ligand 1 is strengthened, so that the rigidity of the organometallic compound represented by the chemical formula 1 can be improved. As a result, the full width at half maximum (FWHM) of the emission peak in the PL spectrum or the EL spectrum for the organometallic compound represented by the chemical formula 1 can be reduced, and the vibronic state of the organometallic compound molecule represented by the chemical formula 1 can be reduced, so that the non-radiative decay can be reduced. Therefore, an electronic device including the organometallic compound represented by the chemical formula 1, for example, an organic light-emitting device, can have high luminescence efficiency and a long lifespan.

The results of evaluating the HOMO energy level, LUMO energy level and T ₁ energy level of compounds 1 to 16 belonging to the organometallic compounds represented by the above chemical formula 1 using the Gaussian 09 program accompanied by molecular structure optimization by density functional theory (DFT) based on B3LYP are as shown in Table 1 below.

Compound No. HOMO(eV) LUMO(eV) T ₁ (eV) 1 -4.798 -1.951 1.988 2 -4.792 -1.948 1.987 3 -4.791 -1.946 1.985 4 -4.678 -1.732 2.049 5 -4.682 -1.785 2.019 6 -4.677 -1.781 2.021 7 -4.610 -1.688 2.038 8 -4.804 -1.987 1.975 9 -4.764 -1.895 1.995 10 -4.798 -1.951 1.988 11 -4.736 -1.875 2.001 12 -4.673 -1.856 2.002 13 -4.647 -1.771 2.007 14 -4.678 -1.712 2.069 15 -4.594 -1.732 1.951 16 -4.674 -1.775 2.019

Meanwhile, according to one embodiment, when R ₂₀ of the organometallic compound represented by the chemical formula 1 does not include a fluoro group (-F) and a cyano group, the organometallic compound represented by the chemical formula 1 can additionally emit light having high chromatic purity (for example, light having a relatively narrow full width at half maximum (FWHM) of an emission peak of an emission spectrum or an electroluminescence spectrum).

According to one embodiment, the full width at half maximum (FWHM) of an emission peak of the emission spectrum or electroluminescence spectrum of the organometallic compound may be 64 nm or less. For example, the full width at half maximum (FWHM) of an emission peak of the emission spectrum or electroluminescence spectrum of the organometallic compound may be in a range of 45 nm to 64 nm, 45 nm to 59 nm, 45 nm to 55 nm, or 49 nm to 55 nm.

Meanwhile, according to another embodiment, the maximum emission wavelength (emission peak wavelength, λ _max ) of the emission spectrum or the electroluminescence spectrum of the organometallic compound may be in a range of 615 nm to 640 nm. For example, the maximum emission wavelength (emission peak wavelength, λ _max ) of the emission peak of the emission spectrum or the electroluminescence spectrum of the organometallic compound may be in a range of 615 nm to 630 nm or 620 nm to 630 nm.

According to another embodiment, the HOMO energy level of the organometallic compound represented by the chemical formula 1 may be -5.300 eV to -5.050 eV, for example, -5.200 eV to -5.100 eV. The HOMO energy level may be measured using cyclic voltamemetry. For example, the HOMO energy level may be measured using the method described in Table 2 below.

According to another embodiment, the LUMO energy level of the organometallic compound represented by the chemical formula 1 may be -2.900 eV to -2.300 eV, for example, -2.700 eV to -2.300 eV. The LUMO energy level may be measured using a UV absorption spectrum. For example, the LUMO energy level may be measured using a method described in Table 2 below.

According to another embodiment, the quantum luminescence efficiency (PLQY in film) of the organometallic compound represented by the chemical formula 1 may be 91% to 100%. For example, the quantum luminescence efficiency of the film of the organometallic compound may be 92% to 100%, 93% to 100%, 94% to 100%, 95% to 100%, 96% to 100%, 97% to 100%, 98% to 100%, 99% to 100%, or 100%. A method for measuring the quantum luminescence efficiency of the film may refer to, for example, Evaluation Example 2.

According to another embodiment, the decay time of the organometallic compound represented by the chemical formula 1 may be 0.9 μs or less, for example, 0.6 μs to 0.8 μs. The decay time may be evaluated from a time-resolved photoluminescence (TRPL) spectrum of the organometallic compound. For example, a method for evaluating the decay time of the organometallic compound may refer to the method described in Evaluation Example 3 of the present specification.

According to another embodiment, the horizontal orientation ratio of the transition diopole moment of the organometallic compound represented by the chemical formula 1 may be 90% to 100%.

For example, the horizontal orientation ratio of the transition dipole moment of the organometallic compound can be, for example, 90% to 100%, 91% to 100%, 92% to 100%, 93% to 100%, 94% to 100%, 95% to 100%, 96% to 100%, 97% to 100%, 98% to 100%, 99% to 100%, or 100%.

The horizontal orientation ratio of the above transition dipole moment can be evaluated using an angle-dependent PL measurement device. For a description of the angle-dependent PL measurement device, see, for example, the angle-dependent PL measurement device described in KR application 2013-0150834. The KR application 2013-0150834 is incorporated herein by reference.

As described above, since the horizontal alignment ratio of the transition dipole moment of the organometallic compound is high, when the organic light-emitting device including the organometallic compound is driven, an electric field is emitted in a direction substantially horizontal to the film including the organometallic compound, so that light loss due to the wavequide mode and/or the surface plasmon polariton mode can be reduced. Light emitted by this mechanism can have high external extraction efficiency (i.e., the efficiency with which light emitted from the organometallic compound is extracted to the outside from a device (e.g., an organic light-emitting device) including a film (e.g., an emitting layer to be described later) including the organometallic compound). Therefore, an electronic device employing the organometallic compound, for example, an organic light-emitting device, can achieve high luminous efficiency.

A method for synthesizing the organometallic compound represented by the above chemical formula 1 can be recognized by those skilled in the art by referring to the synthesis examples described below.

Therefore, the organometallic compound represented by the chemical formula 1 may be suitable for use as a dopant in an organic layer of an organic light-emitting device, for example, an emitting layer among the organic layers. According to another aspect, an organic light-emitting device is provided, including: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, including an emitting layer, and including at least one organometallic compound represented by the chemical formula 1.

The above organic light-emitting device can have excellent driving voltage, excellent external quantum efficiency, excellent roll-off ratio, excellent lifetime, and relatively narrow EL spectrum emission peak full width at half maximum (FWHM) and excellent lifetime characteristics by having an organic layer including an organometallic compound represented by the chemical formula 1 described above.

The organometallic compound represented by the above chemical formula 1 can be used between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound represented by the above chemical formula 1 can be included in the light-emitting layer. At this time, the organometallic compound acts as a dopant, and the light-emitting layer can further include a host (i.e., in the light-emitting layer, the content of the organometallic compound represented by the above chemical formula 1 is less than the content of the host).

In one embodiment, the light-emitting layer can emit red light.

In this specification, “(the organic layer) includes at least one organometallic compound” may be interpreted as “(the organic layer) may include one organometallic compound belonging to the category of the chemical formula 1 or two or more different organometallic compounds belonging to the category of the chemical formula 1.”

For example, the organic layer may include only the compound 1 as the organometallic compound. At this time, the compound 1 may be present in the light-emitting layer of the organic light-emitting device. Alternatively, the organic layer may include the compound 1 and the compound 2 as the organometallic compound. At this time, the compound 1 and the compound 2 may be present in the same layer (for example, the compound 1 and the compound 2 may both be present in the light-emitting layer).

The first electrode is an anode, which is a hole injection electrode, and the second electrode is a cathode, which is an electron injection electrode, or the first electrode is a cathode, which is an electron injection electrode, and the second electrode is an anode, which is a hole injection electrode.

For example, in the organic light-emitting device, the first electrode is an anode, the second electrode is a cathode, the organic layer further includes a hole transport region disposed between the first electrode and the light-emitting layer, and an electron transport region disposed between the light-emitting layer and the second electrode, and the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

In this specification, the term "organic layer" refers to a single and/or multiple layers disposed between the first electrode and the second electrode in an organic light-emitting device. The "organic layer" may include not only an organic compound, but also an organometallic complex including a metal.

Fig. 1 schematically illustrates a cross-sectional view of an organic light-emitting device (10) according to one embodiment of the present invention. Hereinafter, the structure and manufacturing method of an organic light-emitting device according to one embodiment of the present invention will be described with reference to Fig. 1. The organic light-emitting device (10) has a structure in which a first electrode (11), an organic layer (15), and a second electrode (19) are sequentially laminated.

A substrate may be additionally placed below the first electrode (11) or above the second electrode (19). As the substrate, a substrate used in a typical organic light-emitting device may be used, and a glass substrate or transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofing may be used.

The first electrode (11) can be formed, for example, by providing a first electrode material on the upper portion of a substrate using a deposition method or a sputtering method. The first electrode (11) can be an anode. The first electrode material can include a material having a high work function to facilitate hole injection. The first electrode (11) can be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. Indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), or the like can be used as the first electrode material. Alternatively, metals such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or the like can be used.

The first electrode (11) may have a single layer or a multilayer structure including two or more layers. For example, the first electrode (11) may have a three-layer structure of ITO/Ag/ITO.

An organic layer (15) is arranged on top of the first electrode (11).

The above organic layer (15) may include a hole transport region; an emission layer; and an electron transport region.

The above-mentioned hole transport region can be placed between the first electrode (11) and the light-emitting layer.

The above hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

The above hole transport region may include only a hole injection layer or only a hole transport layer. Alternatively, the hole transport region may have a structure of hole injection layer/hole transport layer or hole injection layer/hole transport layer/electron blocking layer, which are sequentially laminated from the first electrode (11).

When the hole transport region includes a hole injection layer, the hole injection layer (HIL) can be formed on the first electrode (11) using various methods such as vacuum deposition, spin coating, casting, or LB.

When forming a hole injection layer by a vacuum deposition method, the deposition conditions vary depending on the compound used as the hole injection layer material, the structure and thermal characteristics of the target hole injection layer, etc., but may be selected in the range of, for example, a deposition temperature of about 100 to about 500°C, a vacuum degree of about 10 ^-8 to about 10 ^-3 torr, and a deposition speed of about 0.01 to about 100 Å/sec, but are not limited thereto.

When forming a hole injection layer by spin coating, the coating conditions vary depending on the compound used as the hole injection layer material, the structure of the desired hole injection layer, and the thermal characteristics, but a coating speed of about 2,000 rpm to about 5,000 rpm, and a heat treatment temperature for removing the solvent after coating may be selected within a temperature range of about 80°C to 200°C, but are not limited thereto.

The above conditions for forming the hole transport layer and electron blocking layer refer to the conditions for forming the hole injection layer.

The above hole transport region is, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, TCTA(4,4',4"-tris(N-carbazolyl)triphenylamine), Pani/DBSA (Polyaniline/Dodecylbenzenesulfonic acid), PEDOT/PSS(Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), Pani/CSA (Polyaniline/Camphor sulfonicacid), PANI/PSS (Polyaniline)/Poly(4-styrenesulfonate): polyaniline)/poly(4-styrenesulfonate)), may include a compound represented by the following chemical formula 201, a compound represented by the following chemical formula 202, or any combination thereof:

<Chemical Formula 201>

<Chemical Formula 202>

In the above chemical formula 201, Ar ₁₀₁ and Ar ₁₀₂ are each independently selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a _salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C _{2 -C 60} alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₁ -C 10 heterocycloalkenyl group, a C 6 -C ₆₀ aryl group, a C ₆ -C ₆₀ aryloxy group, a C ₆ -C It may be a phenylene group, _{a pentarenylene group} , _an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenarenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group or a pentacenylene group, which is unsubstituted or substituted with a 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof.

In the chemical formula 201, xa and xb can be independently integers of 0 to 5, or 0, 1, or 2. For example, xa can be 1 and xb can be 0, but is not limited thereto.

In the above chemical formulas 201 and 202, R ₁₀₁ to R ₁₀₈ , R ₁₁₁ to R ₁₁₉ and R ₁₂₁ to R ₁₂₄ are independently of each other,

hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₁₀ alkyl group (e.g., a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, etc.) or a C ₁ -C ₁₀ alkoxy group (e.g., a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, etc.);

A C 1 -C 10 alkyl group or a C 1 -C 10 alkoxy group substituted or unsubstituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a _hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, and a _phosphoric acid or a salt _thereof , or any combination _thereof ; or

A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group or a pyrenyl group, which is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₁₀ alkyl group, a C _{1 -C} 10 alkoxy group, or any combination thereof;

It could be.

In the above chemical formula 201, R ₁₀₉ may be a phenyl group, a naphthyl group, an anthracenyl group or a pyridinyl group, which is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or any combination thereof.

According to one embodiment, the compound represented by the chemical formula 201 may be represented by the following chemical formula 201A:

<Chemical Formula 201A>

For detailed descriptions of R ₁₀₁ , R ₁₁₁ , R ₁₁₂ and R ₁₀₉ in the above chemical formula 201A, refer to the above.

For example, the hole transport region may comprise one or any combination of the following compounds HT1 to HT21:

The thickness of the hole transport region can be from about 100 Å to about 10000 Å, for example, from about 100 Å to about 1000 Å. If the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer or any combination thereof, the thickness of the hole injection layer can be from about 100 Å to about 10000 Å, for example, from about 100 Å to about 1000 Å, and the thickness of the hole transport layer can be from about 50 Å to about 2000 Å, for example, from about 100 Å to about 1500 Å. When the thicknesses of the hole transport region, the hole injection layer and the hole transport layer satisfy the ranges described above, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

The above-described hole transport region may further include a charge-generating material in addition to the materials described above to enhance conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region.

The charge-generating material can be, for example, a p-dopant. The p-dopant can be, but is not limited to, a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof. For example, the p-dopant can be a quinone derivative such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ), F6-TCNNQ, or the like; a metal oxide such as tungsten oxide and molybdenum oxide; a cyano group-containing compound such as the compound HT-D1 below; or any combination thereof.

The above-mentioned positive hole transport region may further include a buffer layer.

The above buffer layer can play a role in increasing efficiency by compensating for the optical resonance distance according to the wavelength of light emitted from the light emitting layer.

Meanwhile, when the hole transport region includes an electron blocking layer, the electron blocking layer material may include a material that can be used in the hole transport region as described above, a host material described below, or any combination thereof. For example, when the hole transport region includes an electron blocking layer, mCP described below, the compound H21 described above, or any combination thereof may be used as the electron blocking layer material.

An emission layer (EML) can be formed on the upper portion of the above hole transport region using a method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. When the emission layer is formed by a vacuum deposition method or a spin coating method, the deposition conditions and coating conditions vary depending on the compound used, but can generally be selected from a range of conditions almost identical to those for forming the hole injection layer.

The above-described light-emitting layer may include a host and a dopant, and the dopant may include an organometallic compound represented by chemical formula 1 as described herein.

The above host may comprise TPBi, TBADN, ADN (also referred to as “DNA”), CBP, CDBP, TCP, mCP, Compound H50, Compound H51, Compound H52, or any combination thereof:

When the above organic light-emitting device is a full-color organic light-emitting device, the light-emitting layer can be patterned as a red light-emitting layer, a green light-emitting layer, and/or a blue light-emitting layer. Alternatively, the light-emitting layer can have a structure in which a red light-emitting layer, a green light-emitting layer, and/or a blue light-emitting layer are laminated, thereby emitting white light, and various other modifications are possible.

When the above-mentioned light-emitting layer includes a host and a dopant, the content of the dopant may be typically selected in a range of about 0.01 to about 15 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

The thickness of the above-described light-emitting layer may be from about 100Å to about 1000Å, for example, from about 200Å to about 600Å. When the thickness of the above-described light-emitting layer satisfies the range described above, excellent light-emitting characteristics can be exhibited without a substantial increase in driving voltage.

Next, an electron transport region is placed on top of the light-emitting layer.

The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

For example, the electron transport region may have a structure of hole blocking layer/electron transport layer/electron injection layer or electron transport layer/electron injection layer, but is not limited thereto. The electron transport layer may have a single layer or a multilayer structure including two or more different materials.

The formation conditions of the hole blocking layer, electron transport layer, and electron injection layer in the above electron transport region refer to the formation conditions of the hole injection layer.

When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of the following BCP, Bphen and Balq:

Alternatively, the hole blocking layer may include the host, an electron transport layer material described below, an electron injection layer material, or any combination thereof.

The thickness of the hole-blocking layer may be from about 20 Å to about 1000 Å, for example, from about 30 Å to about 600 Å. When the thickness of the hole-blocking layer satisfies the range described above, excellent hole-blocking characteristics can be obtained without a substantial increase in driving voltage.

The electron transport layer may include BCP, Bphen, TPBi, Alq ₃ , Balq, TAZ, NTAZ, or any combination thereof:

Alternatively, the electron transport layer may comprise at least one of the following compounds ET1 to ET25 or any combination thereof:

The thickness of the electron transport layer may be from about 100 Å to about 1000 Å, for example, from about 150 Å to about 500 Å. When the thickness of the electron transport layer satisfies the range described above, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage.

The above electron transport layer may further include a metal-containing material in addition to the materials described above.

The metal-containing material may include a Li complex. The Li complex may include, for example, the following compound ET-D1 or ET-D2.

Additionally, the electron transport region may include an electron injection layer (EIL) that facilitates injection of electrons from the second electrode (19).

The electron injection layer may include LiF, NaCl, CsF, Li ₂ O, BaO, or any combination thereof.

The thickness of the electron injection layer may be from about 1 Å to about 100 Å, for example, from about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

A second electrode (19) is arranged on the organic layer (15). The second electrode (19) may be a cathode. A metal, alloy, electrically conductive compound, or any combination thereof having a relatively low work function may be used as a material for the second electrode (19). As specific examples, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or the like may be used as a material for forming the second electrode (19). Alternatively, various modifications are possible, such as forming a transparent second electrode (19) using ITO or IZO to obtain a front-emitting element.

Above, the organic light-emitting device has been described with reference to Fig. 1, but is not limited thereto.

According to another aspect, a diagnostic composition is provided, comprising at least one organometallic compound represented by the chemical formula 1.

Since the organometallic compound represented by the above chemical formula 1 can provide high luminescence efficiency, a diagnostic composition including the organometallic compound can have high diagnostic efficiency.

The above diagnostic composition can be applied in various ways to various diagnostic kits, diagnostic reagents, biosensors, biomarkers, etc.

Hereinafter, compounds and organic light-emitting devices according to one embodiment of the present invention will be described in more detail with reference to synthetic examples and examples. However, the present invention is not limited to the following synthetic examples and examples. In the following synthetic examples, the amount of 'B' used in place of 'A' is the same as the amount of 'A' used in the expression "'B' was used instead of 'A'" on a molar equivalent basis.

[Example]

Synthesis Example 1 (Compound 1)

Synthesis of compound L1(1)

4-chloro-8-methyl-9-(trifluoromethyl)benzo[f]isoquinoline (24.53 g, 82.95 mmol), 3,5-dimethylphenyl boronic acid (14.93 g, 99.54 mmol), Pd(PPh ₃ ) ₄ (4.80 g, 4.15 mmol), and K ₂ CO ₃ (34.38 g, 248.85 mmol) were mixed with 200 mL of tetrahydrofuran (THF) and 50 mL of distilled water, and then stirred under reflux for 18 hours. After lowering the temperature to room temperature, the organic layer was extracted using methylene chloride (MC). Anhydrous magnesium sulfate (MgSO ₄ ) was added to remove moisture, and then the filtrate was filtered to obtain the solvent. The filtrate was filtered to obtain the solvent. The residue was purified by column chromatography under the conditions of EA (ethyl acetate): Hexane = 1:5 to obtain 24.37 g (80%) of compound L1 (1).

MALDI-TOFMS (m/z): C ₂₃ H ₁₈ F ₃ N (M+) 365.37

Synthesis of compound L1(2)

Compound L1(1) (24.37 g, 66.70 mmol) and iridium chloride (11.75 g, 33.32 mmol) were mixed with 300 mL of ethoxyethanol and 100 mL of distilled water, stirred under reflux for 24 hours to proceed with the reaction, and then the temperature was lowered to room temperature. The resulting solid was separated by filtration, and the solid obtained by thoroughly washing with water/methanol/hexane in that order was dried in a vacuum oven to obtain compound L1(2) (19.00 g, 69%).

Synthesis of compound 1

Compound L1(2) (19.00 g, 11.48 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (13.80 g, 57.40 mmol), and Na ₂ CO ₃ (12.17 g, 114.80 mmol) were mixed with 300 mL of ethoxyethanol and stirred for 24 hours. The mixture obtained therefrom was filtered, and the obtained solid was sufficiently washed with methanol and hexane, and column chromatography was performed under the condition of dichloromethane: n-hexane = 1:1 (v/v) to obtain compound 1 (13.00 g, 55%). Compound 1 was confirmed by mass and HPLC.

HRMS(MALDI) calcd for C ₆₁ H ₆₀ F ₆ IrN ₂ O ₂ : m/z 1159.42, Found: 1159.37

Synthetic example 2 (compound 2)

Compound 2 (11 g, 60%) was obtained using the same method as for synthesizing compound 1 in Synthetic Example 1, except that 3,3,7,7-tetramethylnonane-4,6-dione was used instead of 3,7-diethyl-3,7-dimethylnonane-4,6-dione. Compound 2 was confirmed by mass and HPLC.

HRMS(MALDI) calcd for C ₅₉ H ₅₆ F ₆ IrN ₂ O ₂ : m/z 1131.39, Found: 1131.32

Synthesis Example 3 (Compound 3)

Compound 3 (5 g, 50%) was obtained using the same method as for synthesizing compound 1 in Synthetic Example 1, except that 2,2,6,6-tetramethylheptane-3,5-dione was used instead of 3,7-diethyl-3,7-dimethylnonane-4,6-dione. Compound 3 was confirmed by mass and HPLC.

(HRMS(MALDI) calcd for C ₅₇ H ₅₂ F ₆ IrN ₂ O ₂ : m/z 1160.35, Found: 1160.37

Synthesis Example 4 (Compound 4)

Synthesis of compound L4(1)

4-Chloro-8-fluorobenzo[f]isoquinoline (19.22 g, 82.95 mmol), 3,5-dimethylphenyl boronic acid (14.93 _g , 99.54 mmol), Pd(PPh 3 ) ₄ (4.80 g, 4.15 mmol), and K ₂ CO ₃ (34.38 g, 248.85 mmol) were mixed with 200 mL of tetrahydrofuran (THF) and 50 mL of distilled water, and then stirred under reflux for 18 hours. After lowering the temperature to room temperature, the organic layer was extracted using methylene chloride (MC), and anhydrous magnesium sulfate (MgSO ₄ ) was added to remove moisture. The solvent was removed from the filtrate obtained by filtration under reduced pressure, and the obtained residue was purified through column chromatography under the condition of EA:Hexane = 1:5 to obtain 20.1 g (80%) of compound L4(1).

MALDI-TOFMS (m/z): C ₂₁ H ₁₆ FN (M+) 301.36

Synthesis of compound L4(2)

Compound L4(1) (20.10 g, 66.70 mmol) and iridium chloride (11.75 g, 33.32 mmol) were mixed with 300 mL of ethoxyethanol and 100 mL of distilled water, stirred under reflux for 24 hours to proceed with the reaction, and then the temperature was lowered to room temperature. The resulting solid was separated by filtration, and the solid was thoroughly washed with water/methanol/hexane in that order, and dried in a vacuum oven to obtain compound L4(2) (19.00 g, 69%).

Synthesis of compound 4

Compound L4(2) (19.00 g, 11.48 mmol), 2,2,6,6-tetramethylheptane-3,5-dione (10.56 g, 57.40 mmol), and Na ₂ CO ₃ (12.17 g, 114.80 mmol) were mixed with 300 mL of ethoxyethanol and stirred for 24 hours to proceed with the reaction. The mixture obtained therefrom was filtered, and the obtained solid was sufficiently washed with methanol and hexane, and column chromatography was performed under the condition of dichloromethane: n-hexane = 1:1 (v/v) to obtain compound 4 (13.00 g, 55%). Compound 4 was confirmed by mass and HPLC.

HRMS(MALDI) calcd for C ₅₃ H ₄₈ F ₂ IrN ₂ O ₂ : m/z 975.19, Found: 975.20

Synthesis Example 5 (Compound 5)

Synthesis of compound L5(1)

4-Chloro-7,9-difluorobenzo[f]isoquinoline (20.71 g, 82.95 mmol), 3,5-dimethylphenyl boronic acid ₍ 14.93 g, 99.54 mmol), Pd(PPh 3 ) ₄ (4.80 g, 4.15 mmol), and K ₂ CO ₃ (34.38 g, 248.85 mmol) were mixed with 200 mL of tetrahydrofuran (THF) and 50 mL of distilled water, and then stirred under reflux for 18 hours. After lowering the temperature to room temperature, the organic layer was extracted using methylene chloride (MC), and anhydrous magnesium sulfate (MgSO ₄ ) was added. After adding to remove moisture and filtering, the solvent was removed under reduced pressure from the obtained filtrate, and the obtained residue was purified through column chromatography under the condition of EA:Hexane = 1:5 to obtain 21.30 g (80%) of compound L5(1).

MALDI-TOFMS (m/z): C ₂₁ H ₁₅ F ₂ N (M+) 319.35

Synthesis of compound L5(2)

Compound L5(1) (21.30 g, 66.70 mmol) and iridium chloride (11.75 g, 33.32 mmol) were mixed with 300 mL of ethoxyethanol and 100 mL of distilled water, stirred under reflux for 24 hours to proceed with the reaction, and then the temperature was lowered to room temperature. The resulting solid was separated by filtration, and the solid obtained by thoroughly washing with water/methanol/hexane in that order was dried in a vacuum oven to obtain compound L5(2) (19.00 g, 69%).

Synthesis of compound 5

Compound L5(2) (19.00 g, 11.48 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (13.80 g, 57.40 mmol), and Na ₂ CO ₃ (12.17 g, 114.80 mmol) were mixed with 300 mL of ethoxyethanol and stirred for 24 hours to proceed with the reaction. The mixture obtained therefrom was filtered, and the obtained solid was sufficiently washed with methanol and hexane, and column chromatography was performed under the condition of dichloromethane: n-hexane = 1:1 (v/v) to obtain compound 5 (13.00 g, 55%). Compound 5 was confirmed by mass and HPLC.

HRMS(MALDI) calcd for C ₅₇ H ₅₄ F ₄ IrN ₂ O ₂ : m/z 1067.38, Found: 1067.28

Synthesis Example 6 (Compound 6)

Synthesis of compound L6(1)

4-Chloro-9-fluorobenzo[f]isoquinoline (19.21 g, 82.95 mmol), 3,5-dimethylphenyl boronic acid (14.93 g, 99.54 mmol), Pd( _PPh 3 ) ₄ (4.80 g, 4.15 mmol), and K ₂ CO ₃ (34.38 g, 248.85 mmol) were mixed with 200 mL of tetrahydrofuran (THF) and 50 mL of distilled water, and then stirred under reflux for 18 hours. After lowering the temperature to room temperature, the organic layer was extracted using methylene chloride (MC), and anhydrous magnesium sulfate (MgSO ₄ ) was added to remove moisture. The solvent was removed from the filtrate obtained by filtration under reduced pressure, and the obtained residue was purified through column chromatography under the condition of EA:Hexane = 1:5 to obtain 20.10 g (80%) of compound L6(1).

MALDI-TOFMS (m/z): C ₂₁ H ₁₆ FN (M+) 301.36

Synthesis of compound L6(2)

Compound L6(1) (20.10 g, 66.70 mmol) and iridium chloride (11.75 g, 33.32 mmol) were mixed with 300 mL of ethoxyethanol and 100 mL of distilled water, stirred under reflux for 24 hours to proceed with the reaction, and then the temperature was lowered to room temperature. The resulting solid was separated by filtration, and the solid obtained by thoroughly washing with water/methanol/hexane in that order was dried in a vacuum oven to obtain compound L6(2) (19.00 g, 69%).

Synthesis of compound 6

Compound L6(2) (19.00 g, 11.48 mmol), 3,3,7,7-tetramethylnonane-4,6-dione (13.80 g, 57.40 mmol), and Na ₂ CO ₃ (12.17 g, 114.80 mmol) were mixed with 300 mL of ethoxyethanol and stirred for 24 hours to proceed with the reaction. The mixture obtained therefrom was filtered, and the obtained solid was sufficiently washed with methanol and hexane, and column chromatography was performed under the condition of dichloromethane: n-hexane = 1:1 (v/v) to obtain compound 6 (13.00 g, 55%). Compound 6 was confirmed by mass and HPLC.

HRMS(MALDI) calcd for C ₅₅ H ₅₂ F ₂ IrN ₂ O ₂ : m/z 1003.36, Found: 1003.25

Synthesis Example 7 (Compound 10)

Synthesis of compound L10(1)

4-Chloro-9-(trifluoromethyl)benzo[f]isoquinoline (23.36 g, 82.95 mmol), 3,5-dimethylphenyl boronic acid (14.93 g, 99.54 mmol), Pd(PPh ₃ ) ₄ (4.80 g, 4.15 mmol), and K ₂ CO ₃ (34.38 g, 248.85 mmol) were mixed with 200 mL of tetrahydrofuran (THF) and 50 mL of distilled water, and then stirred under reflux for 18 h. After lowering the temperature to room temperature, the organic layer was extracted using methylene chloride (MC) and washed with anhydrous magnesium sulfate (MgSO ₄ ) was added to remove moisture, filtered, and the solvent was removed under reduced pressure from the obtained filtrate. The obtained residue was purified through column chromatography under the condition of EA:Hexane = 1:5 to obtain 23.43 g (80%) of compound L10(1).

MALDI-TOFMS (m/z): C ₂₂ H ₁₆ FN (M+) 351.36

Synthesis of compound L10(2)

Compound L10(1) (23.43 g, 66.70 mmol) and iridium chloride (11.75 g, 33.32 mmol) were mixed with 300 mL of ethoxyethanol and 100 mL of distilled water, and the mixture was stirred under reflux for 24 hours to proceed with the reaction, after which the temperature was lowered to room temperature. The resulting solid was separated by filtration, and the solid obtained by thoroughly washing with water/methanol/hexane in that order was dried in a vacuum oven to obtain compound L10(2) (19.00 g, 69%).

Synthesis of compound 10

Compound L10(2) (19.00 g, 11.48 mmol), 1-((3r,5r,7r)-adamantan-1-yl)-4,4-dimethylmethane-1,3-dione (15.06 g, 57.40 mmol), and Na ₂ CO ₃ (12.17 g, 114.80 mmol) were mixed with 300 mL of ethoxyethanol and stirred for 24 hours to proceed with the reaction. The mixture obtained therefrom was filtered, and the obtained solid was sufficiently washed with methanol and hexane, and column chromatography was performed under the condition of dichloromethane: n-hexane = 1:1 (v/v) to obtain compound 10 (13.00 g, 55%). Compound 10 was confirmed by mass and HPLC.

HRMS(MALDI) calcd for C ₆₁ H ₅₄ F ₆ IrN ₂ O ₂ : m/z 1153.37, Found: 1153.32

Synthesis Example 8 (Compound 13)

Synthesis of compound L13(1)

4-Chloro-6-fluorobenzo[f]isoquinoline (19.21 g, 82.95 mmol), 3,5-dimethylphenyl boronic acid (14.93 _g , 99.54 mmol), Pd(PPh 3 ) ₄ (4.80 g, 4.15 mmol), and K ₂ CO ₃ (34.38 g, 248.85 mmol) were mixed with 200 mL of tetrahydrofuran (THF) and 50 mL of distilled water, and then stirred under reflux for 18 hours. After lowering the temperature to room temperature, the organic layer was extracted using methylene chloride (MC), and anhydrous magnesium sulfate (MgSO ₄ ) was added to remove moisture. The solvent was removed from the filtrate obtained by filtration under reduced pressure, and the residue obtained was purified through column chromatography under the condition of EA:Hexane = 1:5 to obtain 20.10 g (80%) of compound L13(1).

MALDI-TOFMS (m/z): C ₂₁ H ₁₆ FN (M+) 301.36

Synthesis of compound L13(2)

Compound L13(1) (20.10 g, 66.70 mmol) and iridium chloride (11.75 g, 33.32 mmol) were mixed with 300 mL of ethoxyethanol and 100 mL of distilled water, stirred under reflux for 24 hours to proceed with the reaction, and then the temperature was lowered to room temperature. The resulting solid was separated by filtration, and the solid was thoroughly washed with water/methanol/hexane in that order, and dried in a vacuum oven to obtain compound L13(2) (19.00 g, 69%).

Synthesis of compound 13

Compound L13(2) (19.00 g, 11.48 mmol), 2,2,6,6-tetramethylheptane-3,5-dione (10.56 g, 57.40 mmol), and Na ₂ CO ₃ (12.17 g, 114.80 mmol) were mixed with 300 mL of ethoxyethanol and stirred for 24 hours to proceed with the reaction. The mixture obtained therefrom was filtered, and the obtained solid was sufficiently washed with methanol and hexane, and column chromatography was performed under the condition of dichloromethane: n-hexane = 1:1 (v/v) to obtain compound 13 (13.00 g, 55%). Compound 13 was confirmed by mass and HPLC.

HRMS(MALDI) calcd for C ₅₃ H ₄₈ F ₂ IrN ₂ O ₂ : m/z 975.19, Found: 975.20

Synthesis Example 9 (Compound 16)

Synthesis of compound L16(1)

4-Chloro-7-fluorobenzo[f]isoquinoline (19.21 g, 82.95 mmol), 3,5-dimethylphenyl boronic acid (14.93 g, 99.54 mmol), Pd( _PPh 3 ) ₄ (4.80 g, 4.15 mmol), and K ₂ CO ₃ (34.38 g, 248.85 mmol) were mixed with 200 mL of tetrahydrofuran (THF) and 50 mL of distilled water, and then stirred under reflux for 18 hours. After lowering the temperature to room temperature, the organic layer was extracted using methylene chloride (MC), and anhydrous magnesium sulfate (MgSO ₄ ) was added to remove moisture. The solvent was removed from the filtrate obtained by filtration under reduced pressure, and the residue obtained was purified through column chromatography under the condition of EA:Hexane = 1:5 to obtain 20.10 g (80%) of compound L16(1).

MALDI-TOFMS (m/z): C ₂₁ H ₁₆ FN (M+) 301.36

Synthesis of compound L16(2)

Compound L16(1) (20.10 g, 66.70 mmol) and iridium chloride (11.75 g, 33.32 mmol) were mixed with 300 mL of ethoxyethanol and 100 mL of distilled water, stirred under reflux for 24 hours to proceed with the reaction, and then the temperature was lowered to room temperature. The resulting solid was separated by filtration, and the solid obtained by thoroughly washing with water/methanol/hexane in that order was dried in a vacuum oven to obtain compound L16(2) (19.00 g, 69%).

Synthesis of compound 16

Compound L16(2) (19.00 g, 11.48 mmol), 2,2,6,6-tetramethylheptane-3,5-dione (10.56 g, 57.40 mmol), and Na ₂ CO ₃ (12.17 g, 114.80 mmol) were mixed with 300 mL of ethoxyethanol and stirred for 24 hours to proceed with the reaction. The mixture obtained therefrom was filtered, and the obtained solid was sufficiently washed with methanol and hexane, and column chromatography was performed under the condition of dichloromethane: n-hexane = 1:1 (v/v) to obtain compound 16 (13.00 g, 55%). Compound 16 was confirmed by mass and HPLC.

HRMS(MALDI) calcd for C ₅₃ H ₄₈ F ₂ IrN ₂ O ₂ : m/z 975.19, Found: 975.20

Evaluation Example 1: HOMO and LUMO energy level evaluation

The HOMO and LUMO energy levels of compounds 1 to 6, 10, 13, 16, A to D, and E1 to E3 were evaluated according to the method in Table 2, and the results are shown in Table 3.

HOMO energy level evaluation method Using cyclic voltammetry (CV) (electrolyte: 0.1 M Bu ₄ NClO ₄ / solvent: CH ₂ Cl ₂ / electrode: 3-electrode system (working electrode: GC, reference electrode: Ag/AgCl, auxiliary electrode: Pt)), a potential (V)-current (A) graph of each compound was obtained, and the HOMO energy level of each compound was calculated from the reduction onset of the graph. LUMO energy level evaluation method Each compound was diluted to a concentration of 1x10 ^-5 M in CHCl ₃ , and the UV absorption spectrum was measured at room temperature using a Shimadzu UV-350 Spectrometer. The LUMO energy level was calculated using the optical band gap (Eg) from the edge of the absorption spectrum.

Compound No. HOMO (eV) LUMO (eV) 1 -5.140 -2.572 2 -5.150 -2.571 3 -5.130 -2.571 4 -5.110 -2.460 5 -5.160 -2.600 6 -5.120 -2.500 10 -5.150 -2.571 13 -5.110 -2.521 16 -5.119 -2.530 A -5.010 -2.351 B -5.000 -2.328 C -5.373 -2.487 D -5.908 -3.014 E1 -5.216 -2.722 E2 -5.237 -2.673 E3 -5.166 -2.571

Evaluation example 2: Glow Angja Evaluation of efficiency (PLQY)

Compound H52 and compound 1 were co-deposited at a weight ratio of 98:2 at a vacuum of 10 ^-7 torr to produce a 40 nm thick film.

The photoluminescence quantum yields in film of the above films were evaluated using a Hamamatsu Photonics absolute PL quantum yield measurement system equipped with a xenon light source, a monochromator, a photonic multichannel analyzer, and an integrating sphere, and employing PLQY measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan). The PLQY of compound 1 in film was confirmed, and the results are shown in Table 4.

The PLQY measurements were performed for compounds 2 to 6, 10, 13, 16, A to D, and E1 to E3, respectively, and the results are shown in Table 4.

Compound No. PLQY in film (%) 1 95.0 2 99.9 3 92.0 4 92.7 5 99.4 6 95.8 10 94.4 13 93.7 16 96.7 A 90.5 B 90.2 C 87.5 D 88.0 E1 73.7 E2 74.2 E3 74.8

From the above Table 4, it can be confirmed that compounds 1 to 6, 10, 13, and 16 have superior PLQY (in film) compared to compounds A to D and E1 to E3.

Evaluation example 3: Decay time measurement

Quartz substrates were prepared by cleaning with chloroform and pure water, and then the materials listed in Table 5 were vacuum-deposited at a vacuum of 10 ^-7 torr to prepare films 1 to 6, 10, 13, 16, A to D, and E1 to E3, each having a thickness of 50 nm.

Next, for each of the films 1 to 6, 10, 13, 16, A to D, and E1 to E3 prepared as described above, the PL spectrum was evaluated at room temperature using the FluoTime 300, a TRPL measurement system from PicoQuant, and the PLS340, a pumping source from PicoQuant (excitation wavelength = 340 nanometers, spectral width = 20 nanometers), and the wavelength of the main peak of the spectrum was determined, and the number of photons emitted from each film at the wavelength of the main peak by the photon pulse (pulse width = 500 picoseconds) applied to each film by the PLS340 was repeatedly measured over time based on Time-Correlated Single Photon Counting (TCSPC), thereby obtaining a TRPL curve that could be sufficiently fitted. From the results obtained here, two or more exponential decay functions were fitted to obtain the T _decay (Ex), i.e., the decay time, of each of films 1 to 6, 10, 13, 16, A to D, and E1 to E3, and the results are shown in Table 5. The function used for fitting is as shown in <Formula 1> below, and the largest value of the T _decay obtained from each exponential decay function used for fitting was taken as T _decay (Ex). At this time, the same measurement was repeated once more in the dark state (a state in which the pumping signal incident on the specified film was blocked) for the same measurement time as the measurement time for obtaining the TRPL curve, to obtain a baseline or background signal curve, which was used as the baseline for fitting.

<Formula 1>

Film No. Compounds used in film production Decay time
(decay time)
(㎲) 1 Compound H52: Compound 1 (98:2 weight ratio) 0.718 2 Compound H52: Compound 2 (98:2 weight ratio) 0.700 3 Compound H52: Compound 3 (98:2 weight ratio) 0.730 4 Compound H52: Compound 4 (weight ratio 98:2) 0.773 5 Compound H52: Compound 5 (98:2 weight ratio) 0.704 6 Compound H52: Compound 6 (98:2 weight ratio) 0.794 10 Compound H52: Compound 10 (98:2 by weight) 0.700 13 Compound H52: Compound 13 (98:2 by weight) 0.722 16 Compound H52: Compound 16 (98:2 by weight) 0.682 A Compound H52: Compound A (98:2 weight ratio) 0.907 B Compound H52: Compound B (98:2 weight ratio) 0.911 C Compound H52: Compound C (98:2 weight ratio) 0.961 D Compound H52: Compound D (98:2 weight ratio) 0.952 E1 Compound H52: Compound E1 (98:2 weight ratio) 1.018 E2 Compound H52: Compound E2 (98:2 weight ratio) 1.005 E3 Compound H52: Compound E3 (98:2 weight ratio) 1.091

From Table 5 above, it can be confirmed that compounds 1 to 6, 10, 13, and 16 have superior decay times compared to compounds A to D and E1 to E3.

Example 1

A glass substrate patterned with ITO as an anode was cut to a size of 50 mm x 50 mm x 0.5 mm, ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes each, then irradiated with ultraviolet light for 30 minutes and exposed to ozone for cleaning, and then installed in a vacuum deposition device.

HT3 and F6TCNNQ were vacuum-deposited on the ITO anode at a weight ratio of 98:2 to form a hole injection layer with a thickness of 100 Å, HT3 was vacuum-deposited on the hole injection layer to form a hole transport layer with a thickness of 1350 Å, and then HT21 was vacuum-deposited on the hole transport layer to form an electron blocking layer with a thickness of 300 Å.

Next, H52 (host) and compound 1 (dopant) were co-deposited at a weight ratio of 98:2 on top of the electron blocking layer to form a 400 Å thick light-emitting layer.

Thereafter, ET3 and ET-D1 were co-deposited at a volume ratio of 50:50 on the upper portion of the light-emitting layer to form an electron transport layer with a thickness of 350Å, ET-D1 was vacuum-deposited on the upper portion of the electron transport layer to form an electron injection layer with a thickness of 10Å, and Al was vacuum-deposited on the electron injection layer to form a cathode with a thickness of 1000Å, thereby fabricating an organic light-emitting device having a structure of ITO (1500Å) / HT3 + F6TCNNQ (2 wt%) (100Å) / HT3 (1350Å) / HT21 (300 Å) / H52 + compound 1 (2 wt%) (400Å) / ET3 + ET-D1 (50%) (350Å) / ET-D1 (10Å) / Al (1000Å).

Examples 2 to 9 and Comparative Examples A to D and E1 to E3

An organic light-emitting device was manufactured using the same method as in Example 1, except that the compounds described in Table 6 were used instead of compound 1 as a dopant when forming the light-emitting layer.

Evaluation Example 4: Characteristic Evaluation of Organic Light-Emitting Devices

For each organic light-emitting device manufactured in Examples 1 to 9 and Comparative Examples A to D and E1 to E3, the driving voltage, current density, maximum external quantum efficiency (Max EQE), roll-off ratio, half width of the emission peak of the EL spectrum, color coordinates, and/or lifetime (LT ₉₇ ) were evaluated, and the results are shown in Tables 6 and 7. A current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as evaluation devices, and the lifetime (LT ₉₇ ) (at 3500 nit) was evaluated as the time (hr) required for the luminance to become 97% of the initial luminance of 100%. The lifetime data in Table 7 are expressed as relative values (%). The roll-off ratio was calculated according to the following Equation 20.

<Formula 20>

Roll-off ratio = {1- (efficiency (at 3500nit) / maximum luminous efficacy)} X 100%

Dopant compound
No. Driving voltage
(V) Current density
(㎃/㎠) Max EQE
(%) Roll-off ratio
(%) Example 1 1 4.66 10 30 7 Example 2 2 4.69 10 30.8 8 Example 3 3 4.70 10 30.1 8 Example 4 4 4.61 10 30.8 7 Example 5 5 4.88 10 30.7 8 Example 6 6 4.45 10 35.7 9 Example 7 10 4.81 10 30.0 10 Example 8 13 4.79 10 30.8 8 Example 9 16 4.82 10 30.1 8 Comparative Example A A 4.91 10 27.6 11 Comparative Example B B 4.95 10 28.0 11 Comparative Example C C 5.02 10 26.7 13 Comparative Example D D 4.70 10 22.0 15 Comparative Example E1 E1 5.42 10 23.4 24 Comparative Example E2 E2 5.50 10 24.1 19 Comparative Example E3 E3 5.40 10 24.0 18

Dopant compound
No. Half width
(nm) Fluorescent color Color coordinates
(CIE) LT ₉₇ (at 3500nit)
(relative value, %) Example 1 1 51 Red 0.68, 0.30 150 Example 2 2 50 Red 0.68, 0.30 155 Example 3 3 52 Red 0.68, 0.30 148 Example 4 4 50 Red 0.65, 0.32 145 Example 5 5 52 Red 0.685, 0.295 255 Example 6 6 49 Red 0.67, 0.31 160 Example 7 10 53 Red 0.68, 0.30 160 Example 8 13 50 Red 0.68, 0.30 158 Example 9 16 52 Red 0.68, 0.30 143 Comparative Example A A 73 Red 0.62, 0.37 100 Comparative Example B B 72 Red 0.61, 0.375 103 Comparative Example C C 69 yellow 0.44, 0.52 115 Comparative Example D D 65 yellow 0.42, 0.55 125 Comparative Example E1 E1 60 Red 0.69, 0.29 100 Comparative Example E2 E2 60 Red 0.69, 0.29 100 Comparative Example E3 E3 58 Red 0.688, 0.295 105

From the above Tables 6 and 7, it can be confirmed that the organic light-emitting devices of Examples 1 to 9 have improved driving voltage, improved external quantum efficiency, improved roll-off ratio, and improved lifespan characteristics, compared to Comparative Examples A to D and E1 to E3, while emitting red light with a relatively small half-width.

10: Organic light emitting diode
11: 1st electrode
15: Organic layer
19: Second electrode

Claims (20)

An organometallic compound represented by the following chemical formula 1:
<Chemical Formula 1>

In the above chemical formula 1,
Y ₂ is C,
R ₁ to R ₈ , R ₂₀ and A ₇ are each independently hydrogen, deuterium, -F, a cyano group, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -Si(Q ₃ )(Q ₄ )(Q ₅ ), or -Ge(Q ₃ )(Q ₄ )(Q ₅ ),
d2 is an integer from 0 to 4, and when d2 is 2 or greater, 2 or more R _20s are the same or different from each other,
At least one of R ₁ to R ₈ is independently selected from the group consisting of:
Fluoro group (-F); or
A fluorinated C ₁ -C ₂₀ alkyl group, or a fluorinated C ₃ -C ₁₀ cycloalkyl group, which is unsubstituted or substituted with deuterium, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or any combination thereof;
And,
R ₂₀ does not contain a fluoro group (-F) or a cyano group,
A ₁ to A ₆ are each independently a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group,
Two or more of d2 R ₂₀ may optionally be combined with each other to form a C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _1a or a C ₁ -C ₃₀ heterocyclic group substituted or unsubstituted with at least one R _1a ,
Two or more of A ₁ to A ₇ may optionally be combined with each other to form a C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _1a or a _{C 1} -C ₃₀ heterocyclic group substituted or unsubstituted with at least one R 1a,
The description for the above R _1a is the same as the description for the above A ₇ ,
The group represented by is a group represented by the following chemical formula A(1),

Among the above chemical formula A(1),
Y ₂ is C,
The description for R ₉ to R ₁₂ is the same as the description for R ₂₀ above, respectively.
*' is the binding site with Ir in chemical formula 1,
*" is a bonding site with a neighboring atom in chemical formula 1,
The substituents of the substituted C ₁ -C ₆₀ alkyl group, the substituted C ₂ -C ₆₀ alkenyl group, the substituted C ₁ -C ₆₀ alkoxy group, the substituted C _{3 -C 10} cycloalkyl group, the substituted C ₆ -C ₆₀ aryl group, the substituted C 6 -C ₆₀ aryloxy group, the substituted C ₆ -C ₆₀ arylthio group, the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic heterocondensed polycyclic group are,
deuterium, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, or C ₁ -C ₆₀ alkoxy group;
A C ₁ -C ₆₀ alkyl group, a C ₂ -C _{60 alkenyl group, or a C 1 -C 60} alkoxy group substituted with deuterium, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a _cyano group, or _any combination thereof;
A _{C 3 -C 10} cycloalkyl group, a C _{6 -C} 60 aryl group _{, a C 6} -C ₆₀ aryloxy group, a C ₆ -C ₆₀ arylthio group, a C _{1 -C 60} heteroaryl group, a _{monovalent non} -aromatic _condensed polycyclic group, a _monovalent non-aromatic heterocondensed polycyclic group, or any combination thereof, substituted or unsubstituted with _a C ₃ -C ₁₀ cycloalkyl group, _{a C 6} -C ₆₀ aryl group, a C _{6 -C 60} aryloxy group, a C _{6 -C 60} Arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic heterocondensed polycyclic group;
-Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) or -Ge(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ); or
Any combination of these;
And,
The above Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ are independently of each other,
Hydrogen, deuterium, or -F;
A C ₁ -C ₆₀ alkyl group substituted or unsubstituted with deuterium, a C ₁ -C ₆₀ alkyl group, a C ₆ -C ₆₀ aryl group, or any combination thereof; or
A C ₆ -C ₆₀ aryl group unsubstituted or substituted with deuterium, a C ₁ -C ₆₀ alkyl group, a C ₆ -C ₆₀ aryl group, or any combination thereof;
However, the organometallic compound is not the following compound:

delete In the first paragraph,
An organometallic compound wherein R ₁ to R ₈ , R ₂₀ and A ₇ are, independently of each other, hydrogen, deuterium, -F, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, -Si(Q ₃ )(Q ₄ )(Q ₅ ), or -Ge(Q ₃ )(Q ₄ )(Q ₅ ). In the first paragraph,
R ₁ to R ₈ and A ₇ are independently of each other,
Hydrogen, deuterium, or -F;
A C ₁ -C ₂₀ alkyl group, or a C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted with deuterium, -F, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or any combination thereof; or
-Si(Q ₃ )(Q ₄ )(Q ₅ ), or -Ge(Q ₃ )(Q ₄ )(Q ₅ );
And,
R ₂₀ is,
hydrogen, or deuterium;
A C ₁ -C ₂₀ alkyl group, or a C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted with deuterium, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or any combination thereof; or
-Si(Q ₃ )(Q ₄ )(Q ₅ ), or -Ge(Q ₃ )(Q ₄ )(Q ₅ );
In, organometallic compounds.
delete In the first paragraph,
An organometallic compound, wherein A ₁ to A ₆ are each independently a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group. In the first paragraph,
An organometallic compound wherein A ₁ to A ₆ are each independently a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or a C 1 -C 20 alkyl group, or a C 3 -C 10 cycloalkyl group, which is unsubstituted or substituted with deuterium, -F, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or any combination thereof. In the first paragraph,
At least one of R ₂ to R ₈ ,
Fluoro group (-F); or
A fluorinated C ₁ -C ₂₀ alkyl group, or a fluorinated C ₃ -C ₁₀ cycloalkyl group, which is unsubstituted or substituted with deuterium, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or any combination thereof;
In, organometallic compounds. In the first paragraph,
Among the chemical formula 1 above

An organometallic compound, wherein the group represented by is a group represented by one of the following chemical formulae CY1 to CY84:

Among the chemical formulas CY1 to CY84 above,
T ₂ to T ₈ are independent of each other,
Fluoro group (-F); or
A fluorinated C ₁ -C ₂₀ alkyl group, or a fluorinated C ₃ -C ₁₀ cycloalkyl group, which is unsubstituted or substituted with deuterium, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or any combination thereof;
And,
The description of R ₂ to R ₈ is the same as that described in claim 1, but R ₂ to R ₈ are not hydrogen,
* is the binding site with Ir in chemical formula 1,
*" is a bonding site with a neighboring atom in chemical formula 1. In Article 9,
Among the chemical formulas CY1 to CY84, R ₂ to R ₈ are independently,
deuterium; or
A C ₁ -C ₂₀ alkyl group, or a C ₃ -C ₁₀ cycloalkyl group, which is unsubstituted or substituted with deuterium, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or any combination thereof;
In, organometallic compounds.
delete In the first paragraph,
An organometallic compound, wherein in the above chemical formula A(1), R ₉ and R ₁₁ are each independently a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or a C ₁ -C ₂₀ alkyl group, or a C 3 -C 10 cycloalkyl group, which is unsubstituted or substituted with deuterium, a C 1 -C 20 alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or any combination thereof. In the first paragraph,
An organometallic compound, wherein at least one of A ₁ to A ₆ is, independently, a substituted or unsubstituted C ₂ -C ₆₀ alkyl group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group. In the first paragraph,
The number of carbon atoms contained in the group represented by *-C(A ₁ )(A ₂ )(A ₃ ) in the above chemical formula 1 is 5 or more,
An organometallic compound having 5 or more carbon atoms in the group represented by *-C(A ₄ )(A ₅ )(A ₆ ) in the above chemical formula 1. In the first paragraph,
An organometallic compound in which groups A ₁ to A ₃ represented by *-C(A ₁ )(A ₂ )(A ₃ ) in the above chemical formula 1 are bonded to each other to form a C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _1a or a C ₁ -C ₃₀ heterocyclic group substituted or unsubstituted with at least one R _1a . In the first paragraph,
An organometallic compound, at least one of the following compounds 1 to 16:

First electrode;
second electrode; and
An organic layer disposed between the first electrode and the second electrode, and including a light-emitting layer;
Including,
An organic light-emitting device, wherein the organic layer comprises at least one organometallic compound according to any one of claims 1, 3, 4, 6 to 10, and 12 to 16. In Article 17,
The above first electrode is an anode,
The above second electrode is a cathode,
The organic layer further includes a hole transport region disposed between the first electrode and the light-emitting layer and an electron transport region disposed between the light-emitting layer and the second electrode.
The above hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer or any combination thereof,
An organic light-emitting device, wherein the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. In Article 17,
An organic light-emitting device, wherein the above organometallic compound is included in the above light-emitting layer. delete

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