CN119343035B - Organic electroluminescent devices and electronic devices - Google Patents
Organic electroluminescent devices and electronic devicesInfo
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- CN119343035B CN119343035B CN202310880884.3A CN202310880884A CN119343035B CN 119343035 B CN119343035 B CN 119343035B CN 202310880884 A CN202310880884 A CN 202310880884A CN 119343035 B CN119343035 B CN 119343035B
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Abstract
本申请提供一种有机电致发光器件及电子装置，该有机电致发光器件包括阴极、阳极以及有机层。所述有机层包括有机发光层，所述有机发光层包括第一化合物和第二化合物；所述第一化合物选自式1所示的化合物；所述第二化合物选自式2所示的化合物。
The present application provides an organic electroluminescent device and an electronic device, wherein the organic electroluminescent device includes a cathode, an anode, and an organic layer. The organic layer includes an organic light-emitting layer, and the organic light-emitting layer includes a first compound and a second compound; the first compound is selected from the compound represented by Formula 1; and the second compound is selected from the compound represented by Formula 2.
Description
Technical Field
The application relates to the technical field of organic electroluminescent materials, in particular to an organic electroluminescent device and an electronic device.
Background
In recent years, organic electroluminescent devices (OLEDs) are very popular flat display products at home and abroad because OLED displays have characteristics of self-luminescence, wide viewing angle, short reaction time, high efficiency, wide color gamut, etc.
An organic electroluminescent device (OLED) generally includes an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer may include a hole injection layer, a hole transport layer, a hole assist layer, an electron blocking layer, a light emitting layer (containing a host and dopant materials), a hole blocking layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied to the organic electroluminescent device, holes and electrons are injected into the light emitting layer from the anode and the cathode, respectively. Then, in the light emitting layer, the injected holes recombine with electrons to form excitons. The excitons are in an excited state to release energy outwards, so that the light-emitting layer emits light outwards.
At present, the organic electroluminescent device still has the problem of poor performance in the use process, such as the problems of too high driving voltage, too low luminous efficiency or short service life, which affect the use field of the organic electroluminescent device, so that further research on the field is still necessary to improve the performance of the organic electroluminescent device.
Disclosure of Invention
In view of the foregoing problems of the prior art, an object of the present application is to provide an organic electroluminescent device and an electronic apparatus for improving the performance of the device and the apparatus.
According to a first aspect of the present application, there is provided an organic electroluminescent device comprising a cathode, an anode and an organic layer;
wherein the cathode and the anode are arranged opposite to each other;
The organic layer is located between the cathode and the anode;
the organic layer includes an organic light emitting layer;
the organic light emitting layer includes a first compound and a second compound;
The first compound has a structure shown in formula 1
Either of X and Z is-n=, the other is O or S;
L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms;
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms;
L, L 1 and L 2 are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl of 1 to 5 carbon atoms, haloalkyl of 1 to 5 carbon atoms, deuteroalkyl of 1 to 5 carbon atoms, trialkylsilyl of 3 to 8 carbon atoms, aryl of 6 to 14 carbon atoms, deuteroaryl of 6 to 12 carbon atoms, heteroaryl of 3 to 12 carbon atoms or cycloalkyl of 5 to 10 carbon atoms;
Ar 1 and Ar 2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a group represented by the formula (X-1) or a group represented by the formula (X-2);
Ring a and ring T are each independently selected from benzene rings or naphthalene rings;
Y is O, S or N (Ar);
ar is selected from substituted or unsubstituted aryl with 6-18 carbon atoms, substituted or unsubstituted heteroaryl with 3-12 carbon atoms, substituents in Ar are the same or different and are each independently selected from deuterium, cyano, halogen group, alkyl with 1-5 carbon atoms, deuterated alkyl with 1-5 carbon atoms, halogenated alkyl with 1-5 carbon atoms, trialkylsilyl with 3-8 carbon atoms, aryl with 6-12 carbon atoms, deuterated aryl with 6-12 carbon atoms, heteroaryl with 3-12 carbon atoms or cycloalkyl with 5-10 carbon atoms;
Ar 3 is selected from a substituted or unsubstituted aryl group with 6-30 carbon atoms and a substituted or unsubstituted heteroaryl group with 3-30 carbon atoms;
Ar 1、Ar2 and Ar 3 are the same or different in substituent groups, and are each independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, deuterated alkyl groups with 1-10 carbon atoms, trialkylsilyl groups with 3-12 carbon atoms, triphenylsilyl groups, aryl groups with 6-18 carbon atoms, deuterated aryl groups with 6-18 carbon atoms, heteroaryl groups with 3-18 carbon atoms or cycloalkyl groups with 5-10 carbon atoms, optionally, any two adjacent substituent groups form a saturated or unsaturated 5-13 membered ring;
R 1、R2、R3 and R 4 are each independently selected from hydrogen, deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 18 carbon atoms, deuterated aryl group having 6 to 18 carbon atoms, heteroaryl group having 3 to 18 carbon atoms or cycloalkyl group having 5 to 10 carbon atoms;
n 1 represents the number of R 1, and n 1 is selected from 0,1, 2 or 3;
n 2 represents the number of R 2, and n 2 is selected from 0, 1 or 2;
n 3 represents the number of R 3, and n 3 is selected from 0,1, 2, 3, 4, 5, 6 or 7;
n 4 represents the number of R 4, and n 4 is selected from 0, 1, 2, 3,4, 5, 6, 7 or 8;
the second compound has a structure represented by formula 2:
ring Q is a naphthalene ring;
ar 5 is selected from a group represented by formula (X-3) or a group represented by formula (X-4);
w and V are each independently selected from O or S;
Ar 4、Ar6 and Ar 7 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
L 4、L5 and L 6 are selected from single bond, substituted or unsubstituted arylene group with 6-30 carbon atoms, and substituted or unsubstituted heteroarylene group with 3-30 carbon atoms;
The substituents in L 4、L5、L6、Ar4、Ar6 and Ar 7 are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, deuteroalkyl with 1-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, trialkylsilyl with 3-12 carbon atoms, triphenylsilyl, aryl with 6-20 carbon atoms, heteroaryl with 3-20 carbon atoms or cycloalkyl with 3-10 carbon atoms, optionally any two adjacent substituents form a saturated or unsaturated 3-15 membered ring;
R 5、R6、R7 and R 8 are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms or cycloalkyl having 3 to 10 carbon atoms, n 5 is selected from 0,1, 2,3 or 4;n 6 is selected from 0,1, 2,3, 4,5 or 6;n 7 is selected from 0,1, 2 or 3, and n 8 is selected from 0,1, 2,3, 4,5, 6 or 7.
According to a second aspect of the present application, there is provided an electronic device comprising the organic electroluminescent device of the first aspect.
The luminescent layer host material of the organic electroluminescent device comprises a first compound and a second compound, wherein the first compound is provided with an electron transport material formed by connecting naphtho [2,1-d ] oxazole with triazine through 9-position, the second compound is provided with a compound formed by connecting benzocarbazole as a mother nucleus with aromatic amine, the other two substituents of the aromatic amine comprise dibenzofuran/dibenzothiophene or benzoxazole groups, and the first compound and the second compound are mixed in a certain proportion to form a mixed red light host material. Firstly, the electron transport material used in the application has a special connection mode, on one hand, the electron transport material can maintain a higher first triplet energy level value of the material and has strong carrier transport capacity and high energy transfer capacity, on the other hand, the special connection mode can enable a compound structure to have a certain torsion degree, inhibit excessive accumulation among molecules of the compound and inhibit crystallization of the compound, so that a compound film is endowed with higher stability, secondly, the hole transport material used in the application contains a mother nucleus of benzocarbazole, which has a larger conjugation area and can improve the hole mobility of arylamine compounds, on the other hand, benzofuran/dibenzothiophene and benzoxazole groups have a certain electron withdrawing characteristic compared with aryl groups, and when the electron transport material is connected with triarylamine, the lowest unoccupied orbit (LUMO: lowest unoccupiedmolecular orbital) of molecules can be limited on the benzofuran/dibenzothiophene or benzoxazole groups, so that the electron tolerance of molecules is improved. Therefore, when the first compound and the second compound are combined to be used as the mixed red light main body material, the carrier balance in the light-emitting layer can be obviously improved, the stability of the film is improved, and the light-emitting efficiency and the service life of the device are further improved.
Drawings
The accompanying drawings are included to provide a further understanding of the application, and are incorporated in and constitute a part of this specification, illustrate the application and together with the description serve to explain, without limitation, the application.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
Reference numerals
100. Anode 200, cathode 300, functional layer 310, and hole injection layer
321. First hole transport layer 322, hole adjustment layer 320, hole transport layer 330, and organic light emitting layer
340. Electron transport layer 350, electron injection layer 400, and electronic device
Detailed Description
Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments may be embodied in many different forms and should not be construed as limited to the examples set forth herein, but rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals in the drawings denote the same or similar structures, and thus detailed descriptions thereof will be omitted.
According to a first aspect of the present application, there is provided an organic electroluminescent device comprising a cathode, an anode and an organic layer;
wherein the cathode and the anode are arranged opposite to each other;
The organic layer is located between the cathode and the anode;
the organic layer includes an organic light emitting layer;
the organic light emitting layer includes a first compound and a second compound;
The first compound has a structure shown in formula 1
Either of X and Z is-n=, the other is O or S;
L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms;
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms;
L, L 1 and L 2 are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl of 1 to 5 carbon atoms, haloalkyl of 1 to 5 carbon atoms, deuteroalkyl of 1 to 5 carbon atoms, trialkylsilyl of 3 to 8 carbon atoms, aryl of 6 to 14 carbon atoms, deuteroaryl of 6 to 12 carbon atoms, heteroaryl of 3 to 12 carbon atoms or cycloalkyl of 5 to 10 carbon atoms;
Ar 1 and Ar 2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a group represented by the formula (X-1) or a group represented by the formula (X-2);
Ring a and ring T are each independently selected from benzene rings or naphthalene rings;
Y is O, S or N (Ar);
ar is selected from substituted or unsubstituted aryl with 6-18 carbon atoms, substituted or unsubstituted heteroaryl with 3-12 carbon atoms, substituents in Ar are the same or different and are each independently selected from deuterium, cyano, halogen group, alkyl with 1-5 carbon atoms, deuterated alkyl with 1-5 carbon atoms, halogenated alkyl with 1-5 carbon atoms, trialkylsilyl with 3-8 carbon atoms, aryl with 6-12 carbon atoms, deuterated aryl with 6-12 carbon atoms, heteroaryl with 3-12 carbon atoms or cycloalkyl with 5-10 carbon atoms;
Ar 3 is selected from a substituted or unsubstituted aryl group with 6-30 carbon atoms and a substituted or unsubstituted heteroaryl group with 3-30 carbon atoms;
Ar 1、Ar2 and Ar 3 are the same or different in substituent groups, and are each independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, deuterated alkyl groups with 1-10 carbon atoms, trialkylsilyl groups with 3-12 carbon atoms, triphenylsilyl groups, aryl groups with 6-18 carbon atoms, deuterated aryl groups with 6-18 carbon atoms, heteroaryl groups with 3-18 carbon atoms or cycloalkyl groups with 5-10 carbon atoms, optionally, any two adjacent substituent groups form a saturated or unsaturated 5-13 membered ring;
R 1、R2、R3 and R 4 are each independently selected from hydrogen, deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 18 carbon atoms, deuterated aryl group having 6 to 18 carbon atoms, heteroaryl group having 3 to 18 carbon atoms or cycloalkyl group having 5 to 10 carbon atoms;
n 1 represents the number of R 1, and n 1 is selected from 0,1, 2 or 3;
n 2 represents the number of R 2, and n 2 is selected from 0, 1 or 2;
n 3 represents the number of R 3, and n 3 is selected from 0,1, 2, 3, 4, 5, 6 or 7;
n 4 represents the number of R 4, and n 4 is selected from 0, 1, 2, 3,4, 5, 6, 7 or 8;
the second compound has a structure represented by formula 2:
ring Q is a naphthalene ring;
ar 5 is selected from a group represented by formula (X-3) or a group represented by formula (X-4);
w and V are each independently selected from O or S;
Ar 4、Ar6 and Ar 7 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
L 4、L5 and L 6 are selected from single bond, substituted or unsubstituted arylene group with 6-30 carbon atoms, and substituted or unsubstituted heteroarylene group with 3-30 carbon atoms;
The substituents in L 4、L5、L6、Ar4、Ar6 and Ar 7 are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, deuteroalkyl with 1-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, trialkylsilyl with 3-12 carbon atoms, triphenylsilyl, aryl with 6-20 carbon atoms, heteroaryl with 3-20 carbon atoms or cycloalkyl with 3-10 carbon atoms, optionally any two adjacent substituents form a saturated or unsaturated 3-15 membered ring;
R 5、R6、R7 and R 8 are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms or cycloalkyl having 3 to 10 carbon atoms, n 5 is selected from 0,1, 2,3 or 4;n 6 is selected from 0,1, 2,3, 4,5 or 6;n 7 is selected from 0,1, 2 or 3, and n 8 is selected from 0,1, 2,3, 4,5, 6 or 7.
In the present disclosure, the terms "optional," "optionally," and "optionally" mean that the subsequently described event or circumstance may or may not occur. For example, "optionally, any two adjacent substituents form a saturated or unsaturated 3-to 15-membered ring" includes any two adjacent substituents forming a ring, and any two adjacent substituents each independently exist, and do not form a ring. Any two adjacent atoms can comprise two substituent groups on the same atom, and can also comprise two adjacent atoms which respectively have one substituent group, wherein when the two substituent groups are on the same atom, the two substituent groups can form saturated or unsaturated spiro ring with the atoms which are commonly connected with the two substituent groups, and when the two adjacent atoms respectively have one substituent group, the two substituent groups can be condensed into a ring.
In the present application, the description modes "each of the three modes" and "are independently" and "are used interchangeably, and are to be understood in a broad sense, and they may mean that specific options expressed between the same symbols in different groups do not affect each other, or that specific options expressed between the same symbols in the same groups do not affect each other. For example, the number of the cells to be processed,Wherein each Q is independently 0, 1,2 or 3, and each R ' is independently selected from hydrogen, deuterium, fluorine and chlorine ' and has the meaning that the formula Q-1 represents Q substituent groups R ' on the benzene ring, each R ' can be the same or different, and the options of each R ' are not influenced; the formula Q-2 represents that each benzene ring of the biphenyl has Q substituent groups R ', the number Q of the substituent groups R ' on two benzene rings can be the same or different, each R ' can be the same or different, and the options of each R ' are not influenced each other.
In the present application, such terms as "substituted or unsubstituted" mean that the functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to aryl having a substituent Rc or unsubstituted aryl. Wherein the substituent Rc may be, for example, deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuteroaryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms, arylthio having 6 to 20 carbon atoms or the like. The number of substitutions may be 1 or more.
In the present application, "a plurality of" means 2 or more, for example, 2, 3, 4, 5, 6, etc.
In the present application, the number of carbon atoms of the substituted or unsubstituted functional group refers to all the numbers of carbon atoms.
The hydrogen atoms in the structures of the compounds of the present application include various isotopic atoms of the hydrogen element, such as hydrogen (H), deuterium (D), or tritium (T).
"D" in the structural formula of the compound of the present application represents deuteration.
In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered as aryl groups of the present application unless otherwise indicated. Among them, the condensed ring aryl group may include, for example, a bicyclic condensed aryl group (e.g., naphthyl group), a tricyclic condensed aryl group (e.g., phenanthryl group, fluorenyl group, anthracenyl group), and the like. The aryl does not contain B, N, O, S, P, se, si and other heteroatoms. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, triphenylene, perylenyl, benzo [9,10] phenanthryl, pyrenyl, benzofluoranthracenyl,A base, etc.
In the present application, arylene refers to a divalent or polyvalent group formed by further loss of one or more hydrogen atoms from an aryl group.
In the present application, the terphenyl group includes
In the present application, the substituted or unsubstituted aryl (arylene) group may have 6, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40 carbon atoms. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.
In the present application, the fluorenyl group may be substituted with 1 or more substituents, and in the case where the above fluorenyl group is substituted, the substituted fluorenyl group may be: and the like, but is not limited thereto.
In the present application, aryl groups as substituents are exemplified by, but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, and the like.
In the present application, heteroaryl means a monovalent aromatic ring containing 1, 2,3, 4, 5 or 6 heteroatoms in the ring or derivatives thereof, which may be one or more of B, O, N, P, si, se and S. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, thiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without limitation thereto.
In the present application, the term "heteroarylene" refers to a divalent or polyvalent group formed by further losing one or more hydrogen atoms.
In the present application, the substituted or unsubstituted heteroaryl (heteroarylene) group may have a carbon number selected from 3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、20、21、22、23、24、25、26、27、28、29、30、31、32、33、34、35、36、37、38、39 or 40. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total of 3 to 30 carbon atoms, in other embodiments the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total of 12 to 18 carbon atoms, and in other embodiments the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total of 5 to 12 carbon atoms.
In the present application, heteroaryl groups as substituents are exemplified by, but not limited to, pyridyl, carbazolyl, dibenzothienyl, dibenzofuranyl, benzoxazolyl, benzothiazolyl, benzimidazolyl.
In the present application, a substituted heteroaryl group may be one in which one or more hydrogen atoms in the heteroaryl group are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, and the like.
In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group may be, for example, 1,2,3, 4, 5, 6, 7, 8, 9, 10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.
In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.
In the present application, specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl group, triethylsilyl group, and the like.
In the present application, specific examples of haloalkyl groups include, but are not limited to, trifluoromethyl.
In the present application, the cycloalkyl group having 3 to 10 carbon atoms may have 3, 4, 5, 6, 7, 8 or 10 carbon atoms, for example. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl.
In the present application, the deuterated alkyl group having 1 to 10 carbon atoms has, for example, 1,2, 3, 4, 5, 6, 7, 8 or 10 carbon atoms. Specific examples of deuterated alkyl groups include, but are not limited to, tridentate methyl.
In the present application, the haloalkyl group having 1 to 10 carbon atoms has, for example, 1, 2,3, 4, 5,6, 7, 8 or 10 carbon atoms. Specific examples of haloalkyl groups include, but are not limited to, trifluoromethyl.
In the present application, the ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6 membered ring. The 3-15 membered ring means a cyclic group having 3-15 ring atoms. The 3-15 membered ring is, for example, cyclopentane, cyclohexane, fluorene ring, benzene ring, etc.
In the present application,Refers to chemical bonds that interconnect other groups.
In the present application, the connection key is not positioned in relation to a single bond extending from the ring systemIt means that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule. For example, as shown in the following formula (f), the naphthyl group represented by the formula (f) is linked to other positions of the molecule through two non-positioning linkages penetrating through the bicyclic ring, and the meaning of the linkage includes any one of the possible linkages shown in the formulas (f-1) to (f-10):
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by the formula (X') is linked to other positions of the molecule through an unoositioned linkage extending from the middle of one benzene ring, and the meaning represented by the formula (X '-1) to any one of the possible linkages shown in the formula (X' -4):
By an off-site substituent in the context of the present application is meant a substituent attached by a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system. For example, as shown in formula (Y) below, the substituent R' represented by formula (Y) is attached to the quinoline ring via an unoositioned bond, which means that it includes any one of the possible attachment means shown by formulas (Y-1) to (Y-7):
in some embodiments, the compound of formula 1 is selected from structures represented by the following formulas (1-1) - (1-2):
In some embodiments, in the first compound of formula 1, L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6,7,8,9, 10,11, 12, 13, 14, or 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 6,7,8,9, 10, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.
In some embodiments, in the first compound of formula 1, L is selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, or 12 carbon atoms.
Optionally, the substituents L, L 1 and L 2 are the same or different and are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, deuterated alkyl having 1 to 4 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, phenyl or deuterated phenyl.
In some embodiments, in the first compound of formula 1, L, L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted dibenzothienyl, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted carbazolylene, or a substituted or unsubstituted pyridylene;
Alternatively, the substituents in L, L 1 and L 2 are the same or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl or phenyl.
In some embodiments, in the first compound of formula 1, L 1 and L 2 are each independently selected from the group consisting of a single bond or:
l is selected from the group consisting of a single bond or:
In some embodiments, in the first compound of formula 1, L, L 1 and L 2 are each independently selected from the group consisting of a single bond or:
In some embodiments, in the first compound of formula 1 shown, ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted aryl group having 6,7,8,9, 10,11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms, a group of formula (X-1), or a group of formula (X-2).
Optionally, the substituents in Ar 1 and Ar 2 are each independently selected from deuterium, halogen groups, cyano groups, haloalkyl groups having 1 to 4 carbon atoms, deuterated alkyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 5 to 10 carbon atoms, aryl groups having 6 to 15 carbon atoms, heteroaryl groups having 5 to 12 carbon atoms, trialkylsilyl groups having 3 to 8 carbon atoms or deuterated aryl groups having 6 to 15 carbon atoms, optionally any two adjacent substituents forming a benzene ring or fluorene ring.
In some embodiments, in the first compound of formula 1, ar 1 and Ar 2 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted spirobifluorenyl, a group of formula (X-1), or a group of formula (X-2);
Substituents in Ar 1、Ar2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, tridentate methyl, trimethylsilyl, pentadeuterated phenyl, phenyl or naphthyl;
alternatively, in formula (X-1) and formula (X-2), ring A and ring T are each independently selected from benzene rings or naphthalene rings;
Y is O, S or N (Ar);
ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted terphenyl;
Substituents in Ar, each R 3 and R 4 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl or phenyl.
In some embodiments, in the first compound of formula 1, ar 1 and Ar 2 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted spirobifluorenyl, or the following groups:
Substituents in Ar 1 and Ar 2 and each R 3 and R 4 are the same or different and are each independently selected from deuterium, fluoro, cyano, trimethylsilyl, tridentate methyl, trifluoromethyl, methyl, ethyl, isopropyl, t-butyl, phenyl, pentadeuterated phenyl or naphthyl;
n 3 represents the number of R 3, and n 3 is selected from 0,1, 2, 3, 4, 5, 6 or 7;
n 4 represents the number of R 4 and n 4 is selected from 0, 1, 2, 3,4, 5, 6, 7 or 8.
In some more specific embodiments, in the first compound of formula 1, ar 1 and Ar 2 are the same or different and are each independently selected from the following groups:
in some embodiments, in the first compound of formula 1, ar 1 and Ar 2 are the same or different and are each independently selected from the following groups:
In some embodiments, in the first compound of formula 1, ar 3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and the substituents in Ar 3 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, tridentate methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl, or naphthyl.
In some embodiments, in the first compound of formula 1, ar 3 is selected from the following groups:
in some embodiments, in the first compound of formula 1, ar 3 is selected from the following groups:
in some embodiments, in the first compound of formula 1, Each independently selected from the following groups:
In some embodiments, in the first compound of formula 1, each R 1 and R 2 is independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, tridentate methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, t-butyl, phenyl, pentadeuterated phenyl, or naphthyl.
In some embodiments, the second compound of formula 2 is selected from structures of formulas (2-1) to (2-3) below:
In some embodiments, in the second compound of formula 2, ar 4 and Ar 7 are each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted carbazolyl.
Alternatively, the substituents in Ar 4 and Ar 7 are each independently selected from deuterium, fluoro, cyano, trimethylsilyl, triphenylsilyl, tridentate methyl, trifluoromethyl, methyl, ethyl, isopropyl, t-butyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl.
In some embodiments, in the second compound of formula 2, ar 4 and Ar 7 are each independently selected from the following groups:
In some embodiments, in the second compound of formula 2, ar 4 and Ar 7 are each independently selected from the following groups:
in some embodiments, in the second compound of formula 2, L 4、L5 and L 6 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6,7,8,9, 10,11, 12, 13, 14, or 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 6,7,8,9, 10, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.
Optionally, the substituents in L 4、L5 and L 6 are the same or different and are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, deuteroalkyl having 1 to 4 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms or phenyl.
In some embodiments, in the second compound of formula 2, L 4、L5 and L 6 are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted anthracenylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted dibenzothienyl, a substituted or unsubstituted dibenzofuranylene.
Alternatively, the substituents in L 4、L5 and L 6 are each independently selected from deuterium, fluoro, cyano, trimethylsilyl, tridentate methyl, trifluoromethyl, methyl, ethyl, isopropyl, t-butyl, phenyl or naphthyl.
In some embodiments, in the second compound of formula 2, L 4 and L 5 are each independently selected from a single bond or the following groups:
In some embodiments, in the second compound of formula 2, L 6 is selected from a single bond or the following groups:
In some embodiments, in the second compound of formula 2, ar 5 is selected from the group consisting of substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, and the substituents in L 5 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, tridentate methyl, trifluoromethyl, methyl, ethyl, isopropyl, t-butyl, phenyl, or naphthyl.
In some embodiments, in the second compound of formula 2, ar 5 is selected from the structure of formula (X-4), L 5 is selected from a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group, and the substituents in L 5 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, tridentate methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, or naphthyl.
In some embodiments, in the second compound of formula 2, ar 6 is selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms.
Optionally, the substituents in Ar 6 are each independently selected from deuterium, halogen groups, cyano groups, haloalkyl groups having 1 to 4 carbon atoms, deuterated alkyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 5 to 10 carbon atoms, aryl groups having 6 to 15 carbon atoms, heteroaryl groups having 5 to 12 carbon atoms, trialkylsilyl groups having 3 to 8 carbon atoms or deuterated aryl groups having 6 to 15 carbon atoms, optionally any two adjacent substituents form a benzene ring or fluorene ring.
In some embodiments, in the second compound of formula 2, ar 6 is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazolyl.
Alternatively, substituents in Ar 6 are each independently selected from deuterium, fluoro, cyano, trimethylsilyl, triphenylsilyl, tridentate methyl, trifluoromethyl, methyl, ethyl, isopropyl, t-butyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl.
In some embodiments, in the second compound of formula 2, ar 6 is selected from the following groups:
In some embodiments, in the second compound of formula 2, ar 6 is selected from the following groups:
In some embodiments, in the second compound of formula 2, ar 5 is selected from the following groups:
In some embodiments, in the second compound of formula 2, Selected from the group consisting of:
In some embodiments, in the second compound of formula 2, each R 5 and R 6 is independently selected from hydrogen, deuterium, fluorine, cyano, trimethylsilyl, tridentate methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, t-butyl, phenyl, pentadeuterated phenyl, or naphthyl.
In some embodiments, the first compound is selected from the group consisting of the compounds shown below in A-1~A-336.
In some embodiments, the second compound is selected from the group consisting of compounds shown below as B1-B-282 and C-1~C-252.
Further, in the organic electroluminescent device of the present application, the organic light emitting layer comprises a host material and a dopant. The host material comprises a first compound and a second compound. Generally, the mass ratio of the first compound to the second compound is from 1:99 to 99:1, preferably from 10:90 to 90:10, further preferably from 30:70 to 70:30, more preferably from 40:60 to 60:40, based on the weight (mass) of the two compounds. Still further, the mass ratio of host material and dopant in the organic light emitting layer is 90:10 to 99:1.
In some embodiments, the mass ratio of the first compound (compound of formula 1) to the second compound (compound of formula 2) in the light-emitting layer body of the organic electroluminescent device is 30:70 to 70:30.
Optionally, the mass ratio of the first compound (compound of formula 1) to the second compound (compound of formula 2) in the host material is 35:65, 40:60, 45:55, 50:50, 55:45, 60:40, 65:35.
To obtain a host material mixture, the first compound and the second compound may be mixed in a shaker to obtain a desired weight ratio of the mixture.
In order to form each layer constituting the organic electroluminescent device of the present application, a dry film forming method such as vacuum deposition, sputtering, plasma, ion plating method, etc., or a wet film forming method such as ink jet printing, nozzle printing, slit coating, spin coating, dip coating, flow coating method, etc. may be used.
In addition, the first compound and the second compound may be subjected to film formation in the above-listed methods, typically by a co-evaporation method or a mixed evaporation method. Co-evaporation is a hybrid deposition method in which two or more materials are placed in respective single crucible sources and current is applied to multiple cells simultaneously to evaporate the materials. Hybrid evaporation is a hybrid deposition method in which two or more materials are mixed in one crucible source before evaporation and an electric current is applied to a cell to evaporate the materials.
In some embodiments of the application, the organic electroluminescent device is a phosphorescent device.
In some embodiments of the application, the organic electroluminescent device is a green organic electroluminescent device or a red organic electroluminescent device.
In a second aspect of the present application, there is provided an electronic device comprising the organic electroluminescent device of the first aspect.
In another aspect of the present application, there is also provided a composition comprising a first compound having the structure of formula 1 and a second compound
Either of X and Z is-n=, the other is O or S;
L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms;
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms;
L, L 1 and L 2 are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 5 carbon atoms, haloalkyl having 1 to 5 carbon atoms, deuteroalkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 8 carbon atoms, aryl having 6 to 14 carbon atoms, deuteroaryl having 6 to 12 carbon atoms, heteroaryl having 3 to 12 carbon atoms, cycloalkyl having 5 to 10 carbon atoms;
Ar 1 and Ar 2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a group represented by the formula X-1 or a group represented by the formula X-2;
Ring a and ring T are each independently selected from benzene rings or naphthalene rings;
Y is O, S or N (Ar);
Ar is selected from substituted or unsubstituted aryl with 6-18 carbon atoms and substituted or unsubstituted heteroaryl with 3-12 carbon atoms;
Ar has identical or different substituents and is independently selected from deuterium, cyano, halogen, alkyl with 1-5 carbon atoms, deuterated alkyl with 1-5 carbon atoms, haloalkyl with 1-5 carbon atoms, trialkylsilyl with 3-8 carbon atoms, aryl with 6-12 carbon atoms, deuterated aryl with 6-12 carbon atoms, heteroaryl with 3-12 carbon atoms or cycloalkyl with 5-10 carbon atoms;
Ar 3 is selected from a substituted or unsubstituted aryl group with 6-30 carbon atoms and a substituted or unsubstituted heteroaryl group with 3-30 carbon atoms;
Ar 1、Ar2 and Ar 3 are the same or different in substituent groups, and are each independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, deuterated alkyl groups with 1-10 carbon atoms, trialkylsilyl groups with 3-12 carbon atoms, triphenylsilyl groups, aryl groups with 6-18 carbon atoms, deuterated aryl groups with 6-18 carbon atoms, heteroaryl groups with 3-18 carbon atoms or cycloalkyl groups with 5-10 carbon atoms, optionally, any two adjacent substituent groups form a saturated or unsaturated 5-13 membered ring;
R 1、R2、R3 and R 4 are independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, trialkylsilyl groups having 3 to 12 carbon atoms, triphenylsilyl groups, aryl groups having 6 to 18 carbon atoms, deuterated aryl groups having 6 to 18 carbon atoms, heteroaryl groups having 3 to 18 carbon atoms, or cycloalkyl groups having 5 to 10 carbon atoms;
n 1 represents the number of R 1, and n 1 is selected from 0,1, 2 or 3;
n 2 represents the number of R 2, and n 2 is selected from 0, 1 or 2;
n 3 represents the number of R 3, and n 3 is selected from 0,1, 2, 3, 4, 5, 6 or 7;
n 4 represents the number of R 4, and n 4 is selected from 0, 1, 2, 3,4, 5, 6, 7 or 8;
the second compound has a structure represented by formula 2:
ring Q is a naphthalene ring;
ar 5 is selected from a group represented by formula X-3 or a group represented by formula X-4;
w and V are each independently selected from O or S;
Ar 4、Ar6 and Ar 7 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
L 4、L5 and L 6 are selected from single bond, substituted or unsubstituted arylene group with 6-30 carbon atoms, and substituted or unsubstituted heteroarylene group with 3-30 carbon atoms;
The substituents in L 4、L5、L6、Ar4、Ar6 and Ar 7 are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, deuteroalkyl with 1-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, trialkylsilyl with 3-12 carbon atoms, triphenylsilyl, aryl with 6-20 carbon atoms, heteroaryl with 3-20 carbon atoms or cycloalkyl with 3-10 carbon atoms, optionally any two adjacent substituents form a saturated or unsaturated 3-15 membered ring;
R 5、R6、R7 and R 8 are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms or cycloalkyl having 3 to 10 carbon atoms, n 5 is selected from 0,1, 2,3 or 4;n 6 is selected from 0,1, 2,3, 4,5 or 6;n 7 is selected from 0,1, 2 or 3, and n 8 is selected from 0,1, 2,3, 4,5, 6 or 7.
Alternatively, the mass ratio of the first compound to the second compound in the composition is from 1:99 to 99:1, preferably from 10:90 to 90:10, further preferably from 30:70 to 70:30, more preferably from 40:60 to 60:40.
In some embodiments, the mass ratio of the first compound (compound of formula 1) to the second compound (compound of formula 2) in the composition is 30:70 to 70:30.
The application also provides application of the luminescent layer composition to a luminescent layer of an organic electroluminescent device.
The application also provides an organic electroluminescent device comprising the composition.
The organic electroluminescent device provided by the application comprises an anode and a cathode which are oppositely arranged, and an organic layer. The organic layer includes an organic light emitting layer including a first compound and a second compound.
In some embodiments of the application, the organic electroluminescent device comprises, in order, an anode (e.g., an ITO/Ag/ITO substrate), a hole transport layer, a hole adjustment layer, an organic light emitting layer, an electron transport layer, an electron injection layer, a cathode (e.g., mg-Ag mixture), and an organic capping layer. The hole transport layer is located between the anode and the organic light emitting layer, and the hole adjustment layer is located between the hole transport layer and the organic light emitting layer.
According to a specific embodiment, as shown in fig. 1, the organic electroluminescent device includes an anode 100, a hole injection layer 310, a first hole transport layer 321, a hole adjustment layer (also called a hole auxiliary layer) 322, an organic light emitting layer 330, an electron transport layer 340, an electron injection layer 350, and a cathode 200, which are sequentially stacked.
In the present application, the anode 100 includes an anode material, which is preferably a material having a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof, metal oxides such as zinc oxide, indium Tin Oxide (ITO) and Indium Zinc Oxide (IZO), combined metals and oxides such as ZnO: al or SnO 2: sb, or conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ] (PEDT), polypyrrole and polyaniline, but are not limited thereto. It is preferable to include a transparent electrode containing Indium Tin Oxide (ITO) as an anode.
In the present application, the hole transport layer or the hole adjustment layer may include one or more hole transport materials, respectively, and the hole transport layer material may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, and may specifically be selected from the following compounds or any combination thereof:
in one embodiment, the first hole transport layer 321 consists of HT-1.
In one embodiment, hole adjustment layer 322 is comprised of HT-2.
Optionally, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, and other materials, which are not particularly limited in the present application. The material of the hole injection layer 310 may be selected from, for example, the following compounds or any combination thereof;
In one embodiment of the present application, hole injection layer 310 is comprised of PD and HT-1.
Alternatively, the organic light emitting layer 330 may include the host material and the guest material. Alternatively, the organic light emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be recombined at the organic light emitting layer 330 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.
The host material of the organic light emitting layer 330 includes the first compound and the second compound.
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited in the present application. Guest materials are also known as doping materials or dopants. Fluorescent dopants and phosphorescent dopants can be classified according to the type of luminescence. For example, specific examples of phosphorescent dopants include, but are not limited to,
In one embodiment of the present application, the organic electroluminescent device is a red organic electroluminescent device. In a more specific embodiment, the host material of the organic light emitting layer 330 is composed of the first and second compounds. The guest material may be, for example, RD.
In another embodiment, the organic electroluminescent device is a green organic electroluminescent device. In a more specific embodiment, the host material of the organic light emitting layer 330 is composed of the first and second compounds. The guest material may be, for example, fac-Ir (ppy) 3.
The electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from, but not limited to, bmppiphb, liQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, triazine derivatives, and the like. The material of the electron transport layer 340 comprises LiQ and other electron transport materials that may be selected from, but are not limited to, the following compounds:
in one embodiment of the present application, electron transport layer 340 is comprised of ET-1 and LiQ.
In the present application, the cathode 200 includes a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof, or multilayered materials such as LiF/Al, liq/Al, liO 2/Al, liF/Ca, liF/Al, and BaF 2/Ca. Optionally, a metal electrode comprising magnesium and silver is included as a cathode.
Optionally, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. In one embodiment of the present application, electron injection layer 350 comprises ytterbium (Yb).
The present application not only provides the organic electroluminescent device comprising the compound represented by formula 1 and the compound represented by formula 2 for an organic light emitting layer. The application also provides an electronic device comprising the organic electroluminescent device.
According to one embodiment, as shown in fig. 2, the electronic device provided is an electronic device 400. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other type of electronic device, which may include, for example, but is not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency light, an optical module, etc.
The synthetic methods of the first compound and the second compound of the present application are specifically described below with reference to synthetic examples, but the present application is not limited thereto.
Synthetic examples
Those skilled in the art will recognize that the chemical reactions described herein can be used to suitably prepare many of the heterocyclic compounds of the present application, and that other methods for preparing the compounds of the present application are considered to be within the scope of the present application. For example, the synthesis of those non-exemplified compounds according to the application can be successfully accomplished by modification methods, such as appropriate protection of interfering groups, by use of other known reagents in addition to those described herein, or by some conventional modification of the reaction conditions, by those skilled in the art. None of the compounds of the synthetic methods mentioned in the present application are commercially available starting products.
Synthesis of the first compound:
synthesis of Sub-a 1:
RM-1 (16.21 g,50 mmol), pinacol biborate (14.0 g,55 mmol), potassium acetate (10.8 g,110 mmol) and 1, 4-dioxane (160 mL) were added sequentially to a 500mL three-necked flask under nitrogen atmosphere, stirring and heating were turned on, tris (dibenzylideneacetone) dipalladium (Pd 2(dba)3, 0.46g,0.50 mmol) and 2-dicyclohexylphosphine-2 ',4',6' triisopropylbiphenyl (XPhos, 0.48g,1.0 mmol) were rapidly added until the system warmed to 40℃and the reaction was continued to reflux with stirring overnight. After the system is cooled to room temperature, 200mL of water is added into the system, the mixture is fully stirred for 30min, the reduced pressure suction filtration is carried out, a filter cake is washed to be neutral by deionized water, 100mL of absolute ethyl alcohol is used for leaching, gray solid is obtained, the crude product is pulped once by n-heptane, 200mL of toluene is used for dissolving the crude product, the crude product is filtered through a silica gel column, and the white solid Sub-a1 (13.55 g, 73% yield) is obtained after concentration.
Synthesis of Sub-b 1:
RM-2 (17.20 g,50 mmol), 4-chlorobenzeneboronic acid (8.60 g,55 mmol), tetrakis (triphenylphosphine) palladium (0.58 g,0.5 mmol), anhydrous sodium carbonate (10.60 g,100 mmol), toluene (140 mL), absolute ethanol (35 mL) and deionized water (35 mL) were added sequentially under a nitrogen atmosphere, stirring and heating were turned on, and the temperature was raised to reflux for 8h. After the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. Times.3 times), and the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. Purification by silica gel column chromatography using methylene chloride/n-heptane as the mobile phase afforded an orange-yellow solid (16.2 g, 77% yield).
Referring to synthesis of Sub-c1, sub-B2 to Sub-B14 were synthesized using reactant A shown in Table 1 instead of RM-2, reactant B instead of 4-chlorobenzoic acid
TABLE 1 Synthesis of Sub-b2 to Sub-b14
Synthesis of Compound A-4:
To a 250mL three-necked flask under nitrogen atmosphere, sub-a1 (9.75 g,26.25 mmol), RM-3 (8.60 g,25 mmol), palladium acetate (42 mg,0.25 mmol), 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl (XPhos, 0.24g,0.5 mmol), anhydrous potassium carbonate (6.9 g,50 mmol), tetrabutylammonium bromide (0.8 g,2.5 mmol), toluene (100 mL), tetrahydrofuran (25 mL) and deionized water (25 mL) were sequentially added, and stirring and heating were turned on, and the temperature was raised to reflux reaction for 16h. After the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. Times.3 times), and the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. Purification by silica gel column chromatography using dichloromethane/n-heptane as mobile phase afforded a white solid (9.0 g, 65% yield, m/z=553.20 [ m+h ] +).
Referring to the synthesis of compound A-4, the first compound of the present application in Table 2 was synthesized using reactant C shown in Table 2 instead of RM-3.
TABLE 2 Synthesis of first Compounds of the application
Synthesis of the second compound:
synthesis of Sub-c 1:
RM-4 (18.62 g,50 mmol), 3-aminodibenzofuran (9.16 g,50 mmol), tris (dibenzylideneacetone) dipalladium (0.916 g,1 mmol), (2-dicyclohexylphosphine-2 ',4',6' triisopropylbiphenyl) (XPhos, 0.95g,2 mmol), sodium tert-butoxide (9.61 g,100 mmol) and toluene (180 mL) were sequentially added to a 500mL three-necked flask under nitrogen atmosphere, the mixture was warmed to reflux and stirred overnight, after the system cooled to room temperature, the reaction mixture was poured into 250mL deionized water, stirred thoroughly for 30min, suction filtered, the filter cake was rinsed with deionized water to neutrality (100 mL), and the filter cake was recrystallized with toluene to give an off-green solid Sub-c1 (19.70 g; yield 83%).
Sub-c2 to Sub-c22 were synthesized with reference to Sub-c1 using reactant D shown in Table 3 instead of RM-4 and reactant E instead of 3-aminodibenzofuran.
TABLE 3 Synthesis of Sub-c2 to Sub-c22
Synthesis of Compound B-3:
Sub-c1 (11.86 g,25 mmol), RM-5 (6.66 g,27.5 mmol), tris (dibenzylideneacetone) dipalladium (0.46 g,0.5 mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (Sphos, 0.41g,1 mmol), sodium tert-butoxide (4.80 g,50 mmol) and xylene (xylene, 120 mL) were sequentially added to a 250mL three-necked flask under nitrogen atmosphere, the mixture was warmed to reflux and stirred for reaction overnight, after the system was cooled to room temperature, the organic phase was combined and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure after filtration to obtain the crude product. Purification by silica gel column chromatography using n-heptane as the mobile phase afforded compound B-3 (13.20 g, 83% yield, m/z=636.30 [ m+h ] +) as a white solid.
Referring to the synthesis of compound B-3, the compounds of the present application in Table 4 were synthesized using reactant F instead of Sub-c1 and reactant G instead of RM-5 as shown in Table 4.
TABLE 4 Synthesis of the second Compound of the application
Nuclear magnetism of compound A-242 ：1H-NMR(400MHz,CD2Cl2)δppm：9.36(s,1H),8.86-8.78(m,4H),8.57(d,1H),8.04(d,1H),7.95-7.84(m,7H),7.77(t,1H),7.70-7.44(m,9H),7.41(d,1H),7.18(t,1H),7.08(t,2H);
Nuclear magnetism of compound B-34 ：1H-NMR(400MHz,CD2Cl2)δppm：8.76(d,1H),8.44(d,1H),7.99(d,1H),7.84(d,1H),7.79(d,1H),7.74-7.66(m,2H),7.56-7.40(m,8H),7.38-7.26(m,6H),7.20-7.11(m,5H),7.09-6.97(m,5H),6.93-6.83(m,3H);
Compound C-5 nuclear magnetism ：1H-NMR(400MHz,CD2Cl2)δppm 8.68(d,1H),8.33(d,1H),8.23(d,2H),7.97(d,1H),7.79-7.60(m,5H),7.58-7.32(m,16H),7.24(d,2H),7.12-7.03(m,5H),7.00(d,1H),6.90(s,1H).
Organic electroluminescent device preparation and evaluation:
example 1 preparation of Red organic electroluminescent device
The anode pretreatment is carried out by the following processes in sequence in thicknessThe ITO/Ag/ITO substrate is subjected to surface treatment by utilizing ultraviolet ozone and O2: N2 plasma to increase the work function of an anode, and the surface of the ITO substrate is cleaned by adopting an organic solvent to remove impurities and greasy dirt on the surface of the ITO substrate.
The PD: HT-1 was co-evaporated on an experimental substrate (anode) at an evaporation rate ratio of 3% to 97% to form a film of thicknessIs a Hole Injection Layer (HIL) and then vacuum vapor deposition of HT-1 on the hole injection layerIs provided.
Vacuum evaporating compound HT-2 on the first hole transport layer to form a film having a thickness ofIs provided.
Next, on the second hole transport layer, a red light emitting layer was prepared using a co-evaporation method with compound a-4 as a first host, compound B-177 as a second host, and RD as a dopant. Wherein the first main body and the second main body are uniformly mixed according to the weight ratio of 50:50 to obtain a composition, and the composition of the main body material RD is simultaneously evaporated at the evaporation rate ratio of 98 percent to 2 percent to form the composition with the thickness ofRed light emitting layer (EML).
On the light-emitting layer, the compounds ET-1 and LiQ are co-evaporated at an evaporation rate ratio of 1:1 to formA thick Electron Transport Layer (ETL) on which Yb is evaporated to form a thick layerThen mixing magnesium (Mg) and silver (Ag) at a vapor deposition rate of 1:9, vacuum evaporating on the electron injection layer to form a film with a thickness ofIs provided.
In addition, the thickness of the vacuum evaporation on the cathode isThereby completing the fabrication of the red organic electroluminescent device.
Examples 2 to 40
An organic electroluminescent device was prepared by the same method as in example 1, except that the compound combinations in table 5 below were used instead of the compound combinations in example 1 in the preparation of the light-emitting layer.
Comparative examples 1 to 4
An organic electroluminescent device was prepared by the same method as in example 1, except that the light-emitting layer main body combinations in table 5 below were used instead of the combinations of the compounds A4 and B-177 in example 1, respectively, at the time of producing the light-emitting layers.
Wherein, in preparing each example and comparative example, the structures of the compounds used are as follows:
Performance tests are carried out on the red organic electroluminescent devices prepared in examples 1-40 and comparative examples 1-4, and specifically IVL performance of the devices is tested under the condition of 10mA/cm 2, and the service life of the T95 devices is tested under the condition of 20mA/cm 2, and the test results are shown in Table 5.
TABLE 5
Referring to Table 5 above, it can be seen that the efficiency is improved by at least 11.9% and the lifetime is improved by at least 10.8% when the compound of the present invention is used as a host material for a red organic electroluminescent device.
The preferred embodiments of the present invention have been described in detail above with reference to the accompanying drawings, but the present invention is not limited to the specific details of the above embodiments, and various simple modifications can be made to the technical solution of the present invention within the scope of the technical concept of the present invention, and all the simple modifications belong to the protection scope of the present invention.
Claims (26)
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