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WO2018186662A2 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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Publication number
WO2018186662A2
WO2018186662A2 PCT/KR2018/003926 KR2018003926W WO2018186662A2 WO 2018186662 A2 WO2018186662 A2 WO 2018186662A2 KR 2018003926 W KR2018003926 W KR 2018003926W WO 2018186662 A2 WO2018186662 A2 WO 2018186662A2
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Prior art keywords
group
carbon atoms
substituted
independently
light emitting
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PCT/KR2018/003926
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English (en)
Korean (ko)
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WO2018186662A3 (fr
Inventor
곽지원
김진주
이성재
한수진
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주식회사 엘지화학
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Priority claimed from KR1020180038119A external-priority patent/KR102088506B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201880012161.9A priority Critical patent/CN110383518B/zh
Publication of WO2018186662A2 publication Critical patent/WO2018186662A2/fr
Publication of WO2018186662A3 publication Critical patent/WO2018186662A3/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present invention relates to an organic light emitting device.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, many studies have been conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode.
  • the organic material layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • Patent Document 0001 Korean Patent Publication No. 10-2013-073537 [Contents of the Invention]
  • the present invention provides an organic light emitting device.
  • the present invention is an anode; A cathode provided to face the anode; And at least one organic material layer provided between the anode and the cathode, wherein the organic material layer includes a hole injection layer adjacent to the anode, a hole transport layer provided on the hole injection layer, and the hole transport layer.
  • the hole injection layer comprises a compound selected from the group consisting of compounds represented by the formula 1-1 to 1-2
  • the hole transport layer is an organic light emitting device comprising a compound represented by the formula (2) To provide.
  • R 1 to R 5 are each independently a cyano group, a substituted or unsubstituted carbon number
  • Aryl group of 6 to 60, black is a heteroaryl group having 2 to 60 carbon atoms containing at least one of substituted or unsubstituted 0, N, Si and S,
  • R 15 to R 18 each independently represent a hydrogen, a halogen, a cyano group, an alkyl group having 1 to 40 carbon atoms, a haloalkyl group having 1 to 40 carbon atoms, a haloalkoxy group having 1 to 40 carbon atoms, a substituted or unsubstituted carbon group having 6 to 60 carbon atoms
  • Y 3 and Y 4 are each independently CR 19 or N,
  • Each R 19 independently represents a cyano group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, including one or more of 0, N, Si, and S; ego,
  • Ar 1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 or 60 carbon atoms containing at least one of 0, N, Si, and S,
  • X 1 is an unbonded, single bond, an alkylene group having 1 to 3 carbon atoms, 0 or S, and L 1 and L 2 are each independently a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted group. It is a C2-C60 hetero arylene group containing 1 or more of 0, N, Si, and S,
  • Ar 2 and Ar 3 are each independently selected from the group consisting of the following substituents
  • Ar 4 to Ar 6 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms including at least one of 0, N, Si, and S. ego,
  • X 2 and X 3 are each independently a single bond, 0 or S.
  • FIG. 1 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • the compound selected from the group consisting of the compounds represented by the above formulas (1-1) to 1-2 is used as a material of the hole injection layer, the compound represented by the above formula (2) is used as a material of the hole transport layer is low Driving voltage and / or life characteristics can be improved. [Specific contents to carry out invention]
  • the present invention provides an organic light emitting device in which the hole injection layer includes a compound selected from the group consisting of compounds represented by Formulas 1 to 1 to 1-2, and the hole transport layer includes a compound represented by Formula 2.
  • the non-bond means a case where there is no chemical bond in the moiety represented by X 1 .
  • a single bond means the case where no separate atom exists in the part represented by X ⁇ 1> -X ⁇ 3> .
  • X ⁇ 1> of general formula (2) is a single bond, it is represented as follows.
  • R a is heavy hydrogen, a halogen, a cyano group, a nitro group, an amino group, an alkyl group having 1 to 40 carbon atoms, 1 to 40 haloalkyl group, substituted or unsubstituted 0, N, Si and S containing at least one heteroalkyl group containing 1 to 40 carbon atoms, substituted or unsubstituted 0, N, Si and S at least one It may be a heterohaloalkyl group having 1 to 40 carbon atoms, or an alkenyl group having 2 to 40 carbon atoms.
  • Halogen herein may be fluorine, chlorine, bromine or iodine.
  • the alkyl group having 1 to 40 carbon atoms may be a straight chain, branched chain or cyclic alkyl group.
  • the alkyl group having 1 to 40 carbon atoms is a straight chain alkyl group having 1 to 40 carbon atoms; Linear alkyl groups having 1 to 20 carbon atoms; Linear alkyl groups having 1 to 10 carbon atoms; Branched or cyclic alkyl groups having 3 to 40 carbon atoms; Branched or cyclic alkyl groups having 3 to 20 carbon atoms; Or a branched or cyclic alkyl group having 3 to 10 carbon atoms.
  • the alkyl group having 1 to 40 carbon atoms is methyl group, ethyl group, n-propyl group, i so-propyl group, n-butyl group, i so-butyl group, t-butyl group, n-pentyl group, i so- Pentyl group, neo-pentyl group or cyclonuclear group.
  • the present invention is not limited thereto.
  • the heteroalkyl group having 1 to 40 carbon atoms may be one in which at least one carbon of the alkyl group is independently substituted with 0, N, Si, or S.
  • the heteroalkyl group in which carbon number 1 of the n-butyl group is substituted with 0 is n-propoxy group
  • the heteroalkyl group substituted with N is n-propylamino group
  • the heteroalkyl group substituted with Si is n- It is a propylsilyl group
  • the heteroalkyl group substituted by S is n-propylthio group.
  • examples of the branched alkyl group a heteroalkyl group in which the carbon number 1 of the neo-pentyl group is substituted with 0 is a t-subgroup, a heteroalkyl group substituted with N is a t-butylamino group, and a heteroalkyl group substituted with Si is t A butylsilyl group, wherein the heteroalkyl group substituted by S is a t-butylthio group.
  • annular As an example of the alkyl group, the heteroalkyl group in which the carbon number 2 of the cyclonuclear group is substituted with 0 is 2-tetrahydropyranyl group, and the heteroalkyl group substituted with N is substituted with 2-piperidinyl group
  • the heteroalkyl group is a 1-sil a-cyc lohexyl group
  • the heteroalkyl group substituted with S is a 2-tetrahydrothiopyranyl group.
  • the heteroalkyl group having 1 to 40 carbon atoms may be a straight, branched or cyclic hydroxyalkyl group having 1 to 40 carbon atoms; Linear, branched or cyclic alkoxy groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkoxyalkyl groups having 2 to 40 carbon atoms; Linear, branched or cyclic aminoalkyl groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkylamino groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkylaminoalkyl groups having 1 to 40 carbon atoms; Linear, branched or cyclic silylalkyl (oxy) groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkyl (oxy) silyl groups having 1 to 40 carbon atoms; Linear, branched or cyclic alkyl (oxy) silyl groups having 1 to 40 carbon atoms
  • the heteroalkyl group having 1 to 40 carbon atoms has a hydroxymethyl group, a meso group, an ethoxy group, an n-propoxy group, i so-propoxy group, a t-subspecial group, a cyclonucleooxy group, a hydroxymethyl group, i so -Propoxymethyl group, cyclonuclear methyl group 2-tetrahydropyranyl group, aminomethyl group, methylamino group, n-propylamino group, t-butylamino group, methylaminopropyl group, 2-piperidinyl group, n Propylsilyl group, trimethylsilyl group, dimethylmethoxysilyl group, t-butylsilyl group, 1-si la-cyc lohexyl group, n—propylthio group, t-butylthio group or 2-tetrahydrothiopyranyl (2—tetrahydrothio
  • an alkenyl group having 2 to 40 carbon atoms may be a straight chain, branched chain or cyclic alkenyl group.
  • the alkenyl group having 2 to 40 carbon atoms has a straight chain alkenyl group having 2 to 40 carbon atoms; Linear alkenyl groups having 2 to 20 carbon atoms; C2-C10 and linear alkenyl group; Branched alkenyl groups having 3 to 40 carbon atoms; Branched alkenyl groups having 3 to 20 carbon atoms; Branched alkenyl groups having 3 to 10 carbon atoms; Cyclic alkenyl groups having 5 to 40 carbon atoms; Cyclic alkenyl groups having 5 to 20 carbon atoms; Or a cyclic alkenyl group having 5 to 10 carbon atoms.
  • the alkenyl group having 2 to 40 carbon atoms may be an ethenyl group, propenyl group, butenyl group, pentenyl group, cyclonucleenyl group, or the like.
  • the aryl group having 6 to 60 carbon atoms may be a monocyclic aryl group or a polycyclic aryl group.
  • an aryl group having 6 to 60 carbon atoms has a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • the aryl group having 6 to 60 carbon atoms may be a phenyl group, a biphenyl group or a terphenyl group as a monocyclic aryl group, and as a polycyclic aryl group, a naphthyl group, anthracenyl group, phenanthryl group, triphenylenyl group, pyre Or a phenyl group, a perrylenyl group, a chrysenyl group, or a fluorenyl group.
  • a fluorenyl group may be substituted, and two substituents may be
  • the heteroaryl group having 2 to 60 carbon atoms may be one or more carbons of the aryl group are each independently substituted with 0, N, Si or S.
  • the heteroaryl group substituted with 0 carbon of the fluorenyl group with 0 is a dibenzofuranyl group
  • the heteroaryl group substituted with N is a carbazolyl group
  • the heteroaryl group substituted with Si is a 9-sila-fluoroenyl group
  • the heteroaryl group substituted with S is a dibenzothiophenyl group.
  • a heteroaryl group having 2 to 60 carbon atoms is a heteroaryl group having 2 to 30 carbon atoms; Or a heteroaryl group having 2 to 20 carbon atoms. More specifically, the heteroaryl group having 2 to 60 carbon atoms may be a thiophene group, Furan group, Pyl group, imidazole group, Thiazole group, Oxazole group, Oxadiazole group, Triazole group, Pyridyl group, Bipyridyl group, Pyrimidyl group, Triazine group, Triazole group, Acridyl group, Pyridazine group, Pyrazin group Genyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxa
  • the arylene group means a divalent organic group in which any one hydrogen radical of the aryl group has been removed
  • the heteroarylene group means a divalent organic group in which any one hydrogen radical of the aforementioned heteroaryl group has been removed.
  • one of R 2 and R 3 and one of R 4 and R 5 are cyano groups, R 1 ; The other of R 2 and R 3 ; And each other of R 4 and R 5 is independently a cyano group;
  • R 2 and R 4 may be a cyano group
  • R 1 , R 3 and R 5 may each independently be a phenyl group substituted with at least one member selected from the group consisting of halogen and cyano groups.
  • the compound represented by Formula 1-1 may be the following compound.
  • one of R 15 and R 16 and one of R 17 and R 18 may be each independently halogen, cyano group, alkyl group of 1 to 5 carbon atoms, haloalkyl group of 1 to 5 carbon atoms, and 1 to 5 carbon atoms.
  • Y 3 and Y 4 are CR 19 , and R 19 is each independently a cyano group; Aryl group "of the group having 6 to 20 carbon atoms substituted with one or more selected from the group consisting of halogen and cyano; Or a heteroaryl group having 2 to 20 carbon atoms including one or more of 0, N, Si, and S substituted with one or more substituents selected from the group consisting of halogen and cyano groups.
  • the compound represented by Chemical Formula 1-2 may be selected from the group consisting of the following compounds.
  • the compound represented by Chemical Formula 1-2 may be prepared by a preparation method such as the following formula A.
  • the manufacturing method may be more specific in the production examples to be described later.
  • R 15 , R 16 , R 17 and R 18 are as described above, and further substituents may be further included.
  • Ar 1 in Formula 2 is benzene, naphthalene, biphenyl, terphenyl, triphenylene, phenylnaphthalene, 9, 9-dimethyl fluorene, 9, 9-diphenyl fluorene and spiro [fluorene— 9, 9 ' -Fluorene] may be a monovalent residue from an arene selected from the group consisting of.
  • L 1 and L 2 may each independently be a divalent residue derived from arene selected from the group consisting of benzene, naphthalene, biphenyl, and terphenyl.
  • Ar 4 and Ar 5 may each independently be a monovalent residue derived from arene selected from the group consisting of benzene, naphthalene, biphenyl, and terphenyl.
  • the compound represented by Chemical Formula 2 may be a compound represented by Chemical Formula 2-1.
  • Ar 1 to Ar 3 and X 1 is the same as in Chemical Formula 2,
  • L 3 to L 6 each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted 0, N, Si, and S having at least one of 2 to 50 carbon atoms Heteroarylene group.
  • the compound represented by Formula 2 may be selected from the group consisting of the following compounds.
  • the compound represented by Chemical Formula 2 may be prepared by a preparation method such as the following reaction formula B.
  • the manufacturing method may be more specific in the production examples to be described later.
  • the reaction is carried out in the presence of a palladium catalyst and a base as a Suzuki coupling reaction.
  • the kind of the reaction group and the catalyst used in the reaction system can be appropriately changed.
  • the manufacturing method may be more specific in the production examples to be described later.
  • the organic light emitting device of the present invention includes a cathode provided with both the anode; And at least one raised layer provided between the anode and the cathode.
  • the organic material layer is composed of a multilayered structure of three or more organic material layers. Specifically, the organic material layer includes a hole main pressure layer adjacent to the anode, a hole transport layer provided on the hole injection layer, and a light emitting layer provided on the hole transport layer.
  • the hole injection layer refers to a layer in which holes are injected from an anode and transferred to another organic material layer as an organic material layer contacting the anode of the organic light emitting device. Accordingly, the hole injection layer may also be referred to as a charge generating layer.
  • the hole transport layer is an organic material layer provided on the hole injection layer of the organic light emitting diode, and refers to a layer that transfers holes transferred from the hole injection layer to the light emitting layer and suppresses electrons transferred from the light emitting layer from being transferred to the hole injection layer. Accordingly, the hole transport layer may also be referred to as an electron suppression layer.
  • the organic light emitting device may include an electron transport layer, an electron injection layer, and the like between the light emitting layer and the cathode.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.
  • the organic light emitting device according to the present invention may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • the compound selected from the group consisting of compounds represented by Formulas 1-1 to 1 ′ 2 is included in the hole injection layer 5, and the compound represented by Formula 2 is a hole transport layer 6. It can be included to improve the low driving voltage and / or life characteristics.
  • the organic light emitting device includes a compound selected from the group consisting of compounds represented by Formulas 1-1 to 1-2 in the hole injection layer, and includes a compound represented by Formula 2 in the hole transport layer. It can be prepared by materials and methods known in the art, except that In addition, the plurality of organic material layers may be formed of the same material or different materials.
  • the organic light emitting device according to the present invention may be manufactured by sequentially stacking an electrode of any one of an anode and a cathode, an organic material layer, and another electrode of the anode and the cathode on a substrate.
  • PVD physical vapor deposition
  • An oxide or an alloy thereof may be deposited to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and then a material that may be used as a cathode may be deposited thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (W0 2003/012890).
  • the manufacturing method is not limited thereto.
  • the compounds represented by Formulas 1-1 to 1-2 and the compound represented by Formula 2 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating and the like, but is not limited thereto.
  • the anode material a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material include metals such as vanadium, crumb, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (IT0), indium zinc oxide (IZ0); ⁇ : A1 or SN0 2 : Combination of metal and oxide, such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4— (ethylene-1,2-dioxy) thiophene] (? £ 0 1), polypyrrole and polyaniline, but only It is not limited. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, kaleum, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or Li0 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from the electrode, the material forming the hole injection layer represented by the formula (1-1) to 1-2 Compounds selected from the group consisting of compounds are used. Since the compounds represented by Chemical Formulas 1-1 to 1-2 have been described above in detail, detailed descriptions thereof will be omitted.
  • the compounds represented by Formulas 1-1 to 1-2 have the ability to transport holes, have a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, an electron injection layer of excitons generated in the light emitting layer Alternatively, movement of the electron injection material can be prevented.
  • the compounds of Formulas 1—1 to 1-2 have excellent thin film formation ability.
  • the hole injection layer may further include a hole injection material known in the art to which the present invention pertains, in addition to the compound of Formulas 1-1 to 1-2.
  • HOMO highest occupied molecul ar orbi tal is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole-injecting materials include metal porphyr, oligothiophene, arylamine-based organic matter, nucleonitrile-nucleated azatriphenylene-based organic material, quinacridone-based organic material, and perylene ( perylene) organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer for receiving holes from the hole injection layer and transporting holes to the light emitting layer, and the compound represented by Chemical Formula 2 is used as a material for forming the hole transport layer. Since the compound represented by Chemical Formula 2 has been described in detail above, a detailed description thereof will be omitted.
  • the compound represented by Chemical Formula 2 is suitable for transporting holes from the anode or the hole injection layer to the light emitting layer because of high mobility to the holes.
  • the hole transport layer may further include a hole transport material known in the art. Specific examples of such hole transport materials include, but are not limited to, arylamine-based organics, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and preferably a material having a high quantum efficiency with respect to fluorescence or phosphorescence.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and the styrylamine compound may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer.
  • the electron transporting material is a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer. Suitable.
  • the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically, they are sesame, barium, calcium, ytterbium and samarium, each followed by an aluminum layer or a silver layer.
  • the electron injection layer is a layer for injecting electrons from an electrode, has a capability of transporting electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer
  • the compound which prevents migration to a worm and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and their derivatives, Metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
  • metal complex compound 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc,.
  • the organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type according to the material used.
  • the compound represented by Chemical Formulas 1-1 to 1-2 and the compound represented by Chemical Formula 2 And manufacturing of the organic light emitting device including the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto. Sejoye
  • 1,4—Dibromo-2,5—Diiodobenzene 18.5 g (0.038 mol) to (4-trifluoromethoxy) phenylboronic acid 16.Og (0.078mol), tetrakis (triphenylphosphine) palladium ( 0) It was mixed with 2.2 g, 114 ml of 2M potassium carbonate, and 360 ml of tetrahydrofuran, and reflux stirring was performed for 8 hours on nitrogen conditions.
  • 1,4-dibromo-2, 5-difluoro-3, 6-Taiyo Goto benzene (Compound b-2) 19.9g (0.038mol) of (2-fluoro-4 'trifluoromethoxy ) 17.5 g (0.078 mol) of phenyl boronic acids, 2.2 g of tetrakis (triphenylphosphine) palladium (0), 11M1 of 2M potassium carbonate, and 360 ml of tetrahydrofuran were mixed, and reflux stirring was performed for 12 hours on nitrogen conditions.
  • a glass substrate coated with a thin film having an indium tin oxide (IT0) thickness of 1,000 A was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • IT0 indium tin oxide
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Mi 11 ipore Co. was used as distilled water.
  • the ultrasonic cleaning was performed twice with distilled water for 10 minutes.
  • ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • a hole transport layer was formed by vacuum depositing the following compound [HT1] (1150A), which is a material for transporting holes on the hole injection layer. Subsequently, the following compound [EB1] was vacuum deposited on the hole transport layer with a film thickness of 50 A to form an electron blocking layer.
  • the following compound [BH] and compound [BD] were vacuum-deposited at a weight ratio of 50: 1 on the electron blocking layer at 200 A to form a light emitting layer.
  • the compound [HB 1] was vacuum deposited on the hole transport layer to a film thickness of 50 A to form a hole blocking layer.
  • Compound [ET1] and Compound [LiQ] were vacuum-deposited at a weight ratio of 1: 1 on the hole blocking layer to form a layer for simultaneously injecting and transporting electrons at a thickness of 310A.
  • Lithium fluoride (LiF) and aluminum at a thickness of 2,000A were sequentially deposited on the electron injection and transport layer to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4-0.7 A / sec
  • the lithium fluoride of the cathode was maintained at 0.3 A / sec
  • the aluminum was maintained at the deposition rate of 2 A / sec.
  • the organic light emitting device was manufactured by maintaining 7 to 5 ⁇ 10 ⁇ 6 torr.
  • Comparative Example 1-1 an organic light-emitting device was manufactured in the same manner as in Comparative Example 1-1, except for using the compounds shown in Table 1 below as components for the hole injection layer and the hole transport layer.
  • the device structure used shows the characteristics of basic P-doping devices.
  • the blue organic light emitting device of Comparative Examples 1-5 to 1-16 uses a compound of 1-2-1 to 1-2-3 as the hole injection layer and a compound of compounds ⁇ to HT4 as the hole transport layer. The characteristics of the type element are shown.
  • Example 1-1 and 1-2 when the compound of 2-1 and 2-2 is used as the hole transport layer instead of the compounds of HT-1 to HT-4 in the basic p ⁇ doping device, the luminous efficiency and driving of the organic light emitting device It can be seen that the voltage and lifetime can be improved.
  • Example 1—3 to 1-8 are 2-1 and 2- instead of the compounds of HT-1 to HT-4 in a layer type device using a compound of 1-2-1 magnetic 1-2-3 as a hole injection layer.
  • the compound of 2 is used as the hole transport layer, it can be seen that the luminous efficiency, driving voltage and lifetime of the organic light emitting device can be improved.
  • HT4 has a structure connected by met a and has a relatively low efficiency.
  • the compound of Chemical Formula 1-2 (Tetracyanoquinodimethane: TCNQ core and its derivatives as a core) according to one embodiment of the present specification is used as a layer type hole injection layer material, or the compound of Chemical Formula 1-1
  • the driving voltage, luminous efficiency and lifetime characteristics of the blue organic light emitting device formed by combining the compound of Formula 2 as the hole transport layer can be improved.

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Abstract

La présente invention concerne un dispositif électroluminescent organique.
PCT/KR2018/003926 2017-04-07 2018-04-03 Dispositif électroluminescent organique WO2018186662A2 (fr)

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KR1020180038119A KR102088506B1 (ko) 2017-04-07 2018-04-02 유기 발광 소자

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110600612A (zh) * 2019-06-11 2019-12-20 华东理工大学 基于自组装工程的p-i-n型钙钛矿电池空穴传输层

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CN101473464B (zh) * 2006-06-22 2014-04-23 出光兴产株式会社 应用含有杂环的芳胺衍生物的有机电致发光元件
KR20090028943A (ko) * 2007-09-17 2009-03-20 (주)루디스 정공주입층/정공수송층 물질 및 이를 포함하는유기전계발광소자
EP2915199B1 (fr) * 2012-10-31 2021-03-31 Merck Patent GmbH Dispositif électronique
JP6749892B2 (ja) * 2015-04-10 2020-09-02 保土谷化学工業株式会社 有機エレクトロルミネッセンス素子
KR101873157B1 (ko) * 2016-07-26 2018-07-02 주식회사 엘지화학 유기 발광 소자

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110600612A (zh) * 2019-06-11 2019-12-20 华东理工大学 基于自组装工程的p-i-n型钙钛矿电池空穴传输层

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