CN116239479A - Amino compound and application thereof - Google Patents

Amino compound and application thereof Download PDF

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CN116239479A
CN116239479A CN202310287497.9A CN202310287497A CN116239479A CN 116239479 A CN116239479 A CN 116239479A CN 202310287497 A CN202310287497 A CN 202310287497A CN 116239479 A CN116239479 A CN 116239479A
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unsubstituted
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amino compound
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曹建华
冯静
郭文龙
李程辉
王振宇
唐伟
徐先锋
李利铮
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Zhejiang Bayi Space Time Advanced Materials Co ltd
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Abstract

The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to an amino compound and application thereof. The application of the compound in an organic electroluminescent element can improve the driving voltage and/or current efficiency characteristics.

Description

Amino compound and application thereof
Technical Field
The invention belongs to the technical field of organic electroluminescence, and particularly relates to an amino compound and application thereof in organic electroluminescent materials and luminous elements.
Background
Most of the materials used in the organic electroluminescent element are pure organic materials or organometallic complexes of organic materials and metals, and they are classified into hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, and the like, depending on the application. Here, an organic substance having a relatively small ionization energy is mainly used as the hole injection substance or the hole transport substance, and an organic substance having a relatively large electronegativity is mainly used as the electron injection substance or the electron transport substance. Further, the substance used as the light-emitting auxiliary layer preferably satisfies the following characteristics:
first, the materials used in the organic electroluminescent element need to have good thermal stability because joule heat is generated by charge transfer inside the organic electroluminescent element, and conventionally, the glass transition temperature of the materials generally used as hole transport layers is low, and thus, a phenomenon occurs in which light emission efficiency is lowered due to crystallization occurring at the time of driving at low temperature. Second, in order to reduce the driving voltage, it is necessary that the organic material adjacent to the cathode and anode is designed to have a small charge injection barrier and a high charge mobility. Third, there is always an energy barrier at the interface of the electrode and the organic layer, and at the interface of the organic layer and the organic layer, and some charges are inevitably accumulated, so that it is necessary to use a substance excellent in electrochemical stability.
The organic electroluminescent device generally includes an anode, a hole injection layer, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer, and a cathode, which are sequentially stacked. When voltage is applied to the cathode and the anode, the two electrodes generate an electric field, electrons at the cathode side move to the electroluminescent layer under the action of the electric field, holes at the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state to release energy outwards, so that the electroluminescent layer emits light.
In the prior art, KR1020180113731, CN201710407382.3, CN2016101835 87.3, CN201380045022.3, CN201180044705.8, CN201910765403.8, etc., disclose materials that can be used to prepare hole transport layers in organic electroluminescent devices. However, there remains a need to continue to develop new materials to further improve the performance of electronic components.
Disclosure of Invention
The invention aims to provide an amino compound, an organic electroluminescent material, a light-emitting element and a consumer product, which are used for improving the performance of the organic electroluminescent element.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
An amino compound has a structural general formula shown in a formula (I):
Figure BDA0004140320760000011
wherein X is 1 、X 2 、X 3 、X 4 Each independently selected from N or CR 5 Or any two adjacent X 1 And X 2 、X 2 And X 3 、X 3 And X 4 Represents a group represented by formula (II) or formula (III);
Figure BDA0004140320760000012
z each independently represents CR 6 Or N; and two adjacent "≡" groups are indicated for the adjacent groups X in formula (I) 1 And X 2 、X 2 And X 3 、X 3 And X 4 ；
G represents O, S, se, CR 7 R 8 、SiR 7 R 8 Or NR (NR) 9 ；
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 Are identical to or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 ～C 30 Alkyl, substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 3 ～C 30 Cycloalkyl, substituted or unsubstituted C 2 ～C 50 Heteroaryl, substituted or unsubstituted C 1 ～C 30 Alkoxy, substituted or unsubstituted C 6 ～C 50 Aryloxy, substituted or unsubstituted C 1 ～C 30 Alkylthio, substituted or unsubstituted C 5 ～C 50 Arylthio, substituted or unsubstituted C 1 ～C 30 Alkylamino, substituted or unsubstituted C 5 ～C 50 Arylamine group, substituted or unsubstituted C 1 ～C 30 Alkylsilyl, substituted or unsubstituted C 5 ～C 50 Arylsilyl, cyano, halogen or a group of formula (IV), any adjacent two or more R 1 ～R 9 Can be optionally joined or fused to form a substituted or unsubstituted ring, with or without heteroatoms N, O, S, P, B, si or Se in the ring formed, and at R 1 ～R 6 At least one of them is a group represented by the formula (IV);
Figure BDA0004140320760000021
l is selected from single bond, substituted or unsubstituted C 6 ～C 50 Arylene, substituted or unsubstituted C 2 ～C 50 A group consisting of heteroarylenes;
m is selected from integers of 0 to 5;
Ar 1 、Ar 2 each independently selected from the group consisting of substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 5 ～C 50 Arylamine group, substituted or unsubstituted C 6 ～C 50 Condensed aryl, substituted or unsubstituted C 2 ～C 50 Heteroaryl groups;
the dotted line represents the attachment site of the group;
R 3 、R 4 respectively representing one or more to saturated substitutions.
The alkyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. As non-limiting examples thereof, there are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, and the like;
aryl groups in the sense of the present invention contain 6 to 60 carbon atoms, heteroaryl groups contain 2 to 60 carbon atoms and at least one heteroatom, provided that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. In this case, two or more rings of the heteroaryl group may be attached to each other simply or in a condensed form, or may further include a condensed form with the aryl group. As non-limiting examples of aryl and heteroaryl groups, in particular groups selected from the following: phenyl, naphthyl, anthryl, benzanthraceyl, phenanthryl, pyrenyl,
Figure BDA0004140320760000023
Radicals, perylene radicals, fluorescenceAnthracenyl, naphthacene, pentacenyl, benzopyrene, biphenyl, terphenyl, trimeric phenyl, tetrabiphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, triphenylenyl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, cis-or trans-indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzocarbazolyl, dibenzocarbazolyl, azadibenzo [ g, id]Naphtho [2,1,8-cde]Azulene, triindenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo [5,6 ]]Quinolinyl, benzo [6,7]Quinolinyl, benzo [7,8]Quinolinyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthamidinyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthazolyl, anthracoxazolyl, phenanthrooxazolyl, isoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazabenzophenanthryl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl phenazinyl, phenoxazinyl, phenothiazinyl, fluororubenyl, naphthyridinyl, azacarbazolyl, benzocarboline, carboline, phenanthroline, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,3, 4-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, naphthyridinyl, quinazolinyl, and benzothiadiazolyl or combinations thereof.
"halogen" or "halogen atom" as used herein means a member selected from fluorine, chlorine, bromine or iodine.
Further, the amino compound is selected from the group consisting of the structures shown below:
Figure BDA0004140320760000022
/>
Figure BDA0004140320760000031
wherein the symbols used are as defined above.
Further, the R 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, isopropyl, isobutyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenyl
Figure BDA0004140320760000032
A group selected from the group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, and a group represented by formula (IV), and wherein R 1 ～R 6 At least one of them is a group represented by the formula (IV).
Further, the R 7 、R 8 Each occurrence is independently selected from the group consisting of hydrogen, deuterium, methyl, substituted or unsubstituted phenylA substituted or unsubstituted fluorenyl group.
Further, the R 9 At each occurrence is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenyl
Figure BDA0004140320760000033
A group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group.
Further, m is selected from 0, 1 or 2.
Further, the Ar 1 、Ar 2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenyl
Figure BDA0004140320760000034
A group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group.
In accordance with an embodiment of the present invention,the R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently selected from the group consisting of hydrogen, deuterium, tert-butyl, substituted or unsubstituted phenyl, or formula (IV), and at R 1 ～R 6 At least one of them is a group represented by the formula (IV).
According to an embodiment of the invention, the R 7 、R 8 Each occurrence is independently selected from the group consisting of methyl, substituted or unsubstituted phenyl, substituted or unsubstituted fluorenyl.
According to an embodiment of the invention, the R 9 At each occurrence selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene.
Heteroalkyl in the sense of the present invention means a hydrogen atom or-CH on an alkyl radical 2 Substituted with at least one heteroatom selected from halogen, nitrile, N, O, S or silicon, as non-limiting examples, difluoromethyl, trifluoromethyl, trifluoroethyl, pentafluoroethyl, nitrile, acetonitrile, methoxymethyl, methoxyethyl, trimethylsilyl, triisopropylsilyl and the like. Haloalkyl refers to the partial substitution or total substitution of a hydrogen atom on an alkyl group with a halogen, and as non-limiting examples there are fluorotoluene, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoroethyl, pentafluoroethyl and the like.
Alkenyl or alkynyl groups useful in the present invention contain at least two carbon atoms, and are preferably considered to mean, by way of non-limiting example, the following groups: cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, or octynyl.
Alkoxy, alkylthio, preferably alkoxy or alkylthio having 1 to 40 carbon atoms, as used in the present invention is understood to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octoxy, cyclooctoxy, 2-ethylhexyloxy, pentafluoroethoxy and 2, 2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2-trifluoroethylthio, ethyleneoxy, ethylenethio, propyleneoxy, propylenethio, butyleneoxy, pentyleneoxy, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexene oxy, cyclohexene thio, ethynyloxy, ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.
In general, cycloalkyl, cycloalkenyl groups of the present invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, wherein one or more-CH 2 The radical may be replaced by N, O or S to form heterocycloalkyl, heterocycloalkenyl, e.g. one of the cyclopentyl groups-CH 2 -the radical is replaced by O to form one of the groups-CH in the tetrahydrofuranyl, cyclohexyl 2 -the group is replaced by O to form tetrahydropyranyl, etc.; in addition, one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups.
Aryloxy as used herein refers to R' O - The monovalent functional group represented by R' is an aryl group having 6 to 60 carbon atoms. As non-limiting examples of such aryloxy groups, there are phenoxy, naphthoxy, biphenyloxy, and the like.
Arylthio as used herein means R "S - The monovalent functional group represented by R' is an aryl group having 6 to 60 carbon atoms. As non-limiting examples of such arylthio groups, phenylthio, naphthylthio, biphenylthio and the like are mentioned.
The alkylsilyl group used in the present invention means a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, and the number of carbon atoms constituting the alkylsilyl group is at least 3, and as non-limiting examples of the alkylsilyl group, there are trimethylsilyl group, triethylsilyl group and the like. Aryl silicon group refers to alkyl silicon group substituted with at least one aryl group having 6 to 60 carbon atoms, and examples of the alkyl silicon group include phenyl dimethyl silicon group, naphthyl dimethyl silicon group, phenyl diethyl silicon group, diphenyl methyl silicon group, diphenyl ethyl silicon group, triphenyl silicon group, and the like.
"alkylcarbonyl", "alkoxycarbonyl", "arylcarbonyl", "arylborocarbonyl", "alkylborocarbonyl" in the sense of the present invention means a substituted carbonyl (-COR) wherein R is preferably selected from the group consisting of alkyl, alkoxy, cycloalkyl, aryl, heteroaryl, arylboronyl, alkylboronyl.
The arylphosphorus group used in the present invention means a diarylphosphorus group substituted with an aryl group having 6 to 60 carbon atoms, and as non-limiting examples of the arylphosphorus group, there are diphenylphosphorus group, bis (4-trimethylsilylbenzene) phosphorus group and the like. The phosphorus atom of the aryl phosphorus oxide group is the diaryl phosphorus group is oxidized to the highest valence state.
The arylboron group used in the present invention means a diarylboroyl group substituted with an aryl group having 6 to 60 carbon atoms, and as non-limiting examples of the arylboron group, there are diphenyl boron group, bis (2, 4, 6-trimethylbenzene) boron group and the like. The alkylboryl group means a dialkylboryl group substituted with an alkyl group having 1 to 40 carbon atoms, and as non-limiting examples of the alkylboryl group, there are di-t-butylboryl group, diisobutylboryl group and the like.
The arylalkyl group according to the present invention means an alkyl group in which at least one hydrogen atom of a straight or branched saturated hydrocarbon having from 1 to 40 carbon atoms is substituted with an aryl group having from 6 to 60 carbon atoms, and as a non-limiting example, phenylmethyl group, diphenylmethyl group, triphenylmethyl group, 2-phenylethyl group, 3-phenylpropyl group and the like can be mentioned.
Alkylaryl according to the present invention refers to an aryl group in which at least one hydrogen atom of the aryl group having from 6 to 60 carbon atoms is substituted with a straight or branched saturated hydrocarbon having from 1 to 40 carbon atoms, and as a non-limiting example, methylphenyl, dimethylphenyl, trimethylphenyl, tert-butylphenyl, isopropylphenyl and the like can be mentioned.
The substituents of the substituted alkyl, substituted aryl, substituted heteroaryl, substituted arylamine, substituted condensed aryl, substituted arylene, substituted heteroarylene described herein are each independently selected from at least one of the group consisting of: deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, C 1 -C 40 Alkyl, C 1 -C 40 Haloalkyl, C 2 -C 40 Alkenyl, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy, C 1 -C 40 Alkylthio, C 3 -C 40 Cycloalkyl, C 3 -C 40 Cycloalkenyl, 3-to 7-membered heterocycloalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, unsubstituted or substituted by one or more C 6 -C 60 Aryl-substituted 3-to 30-membered heteroaryl, unsubstituted or deuterated, one or more C 1 -C 40 C substituted with at least one of an alkyl group and one or more 3-to 30-membered heteroaryl groups 6 -C 60 Aryl, tris (C) 1 -C 40 ) Alkylsilyl, tri (C) 6 -C 60 ) Aryl silicon based, di (C) 1 -C 40 ) Alkyl (C) 6 -C 60 ) Aryl silicon base, C 1 -C 40 Alkyldi (C) 6 -C 60 ) Aryl silicon base, C 1 -C 40 Alkylcarbonyl, C 1 -C 40 Alkoxycarbonyl group, C 6 -C 60 Arylcarbonyl, di (C) 6 -C 60 ) Arylborocarbonyl groups of di (C) 1 -C 40 ) Alkyl boron carbonyl, C 1 -C 40 Alkyl (C) 6 -C 60 ) Arylborocarbonyl, C 6 -C 60 Aryl (C) 1 -C 40 ) Alkyl, C 1 -C 40 Of alkyl (C) 6 -C 60 ) Aryl groups.
Arylene in the present invention means a divalent functional group obtained by removing two hydrogen atoms from an aromatic hydrocarbon having 6 to 60 carbon atoms. As non-limiting examples thereof, there are phenylene, naphthylene, phenanthrylene, anthrylene, fluorenylene, spirobifluorenylene and the like.
The heteroarylene or heteroarylene in the present invention means a divalent functional group obtained by removing two hydrogen atoms from a heteroarene having 2 to 60 carbon atoms. As non-limiting examples thereof, there are a pyridyl group, a quinolyl group, an isoquinolyl group, a carbolinyl group, a pyrimidyl group, a triazinyl group and the like.
Arylene and heteroarylene as divalent functional groups with NAr according to the foregoing 1 Ar 2 Preferably, the L is selected from a single bond or a group consisting of the groups III-1 to III-24:
Figure BDA0004140320760000051
wherein X is selected from O, S, se, CR ’ R”、SiR ’ R' or NAr ’ ；
Z 11 、Z 12 、Z 13 、Z 14 Each independently selected from the group consisting of hydrogen, deuterium, halogen atoms, hydroxyl, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1 -C 60 Alkyl, C of (2) 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Is C 3 -C 60 Cyclic olefin group, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Aryl sulfide group, or substituted or unsubstituted C 2 -C 60 Heteroaryl groups;
y1 represents an integer of 1 to 4; y2 represents an integer of 1 to 6; y3 represents an integer of 1 to 3; y4 represents an integer of 1 to 5; y5 represents an integer of 1 or 2;
R ’ r' are each independently selected from C 1 -C 60 Alkyl, C of (2) 1 -C 60 Is optionally substituted C 6 -C 60 Aryl, substituted or unsubstitutedC of (2) 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 Heteroaryl group, R ’ And R "may optionally be joined or fused to form one or more additional substituted or unsubstituted rings with or without one or more heteroatoms N, P, B, O or S in the ring formed; preferably, R ’ R' is methyl, phenyl or fluorenyl;
Ar ’ selected from C 1 -C 60 Alkyl, C of (2) 1 -C 60 Heteroalkyl of (C) 3 -C 60 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups; preferably, ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;
Wherein the dotted line represents the attachment site of the group.
Preferably, X is selected from O or S.
Preferably, L is selected from a single bond or a group consisting of the groups shown in III-1 to III-15, III-24 below:
Figure BDA0004140320760000061
preferably, said Z 11 、Z 12 、Z 13 、Z 14 Each independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile groups.
Further, the amino compound is selected from one or more of the following structures B1007-B1090:
Figure BDA0004140320760000062
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Figure BDA0004140320760000071
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Figure BDA0004140320760000081
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Figure BDA0004140320760000091
as used herein, "combination thereof" or "group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can contemplate from the applicable list. For example, the alkyl and deuterium atoms can combine to form a partially or fully deuterated alkyl group; halogen and alkyl groups may combine to form haloalkyl substituents such as trifluoromethyl and the like; and halogen, alkyl and aryl may combine to form a haloaralkyl.
An organic electroluminescent material comprising the amino compound; the organic electroluminescent material comprising the amino compound according to the invention has a carrier transporting capacity.
The organic electroluminescent material may be constituted by using the amino compound of the present invention alone, or may contain other compounds at the same time.
Preferably, the organic electroluminescent material is a hole injection layer material, a hole transport layer material, a hole blocking layer material, a light emitting layer material, an electron transport layer material, an electron injection layer material, a capping layer (CPL layer for short) material, or an electron blocking layer material.
The invention also provides application of the amino compound in preparation of the organic electroluminescent element.
The present invention also provides an organic electroluminescent element comprising: a first electrode, a second electrode, a CPL layer and more than one organic layer arranged between the first electrode and the second electrode; at least one of the organic layer and the CPL layer comprises the amino compound.
The organic electroluminescent element comprises a cathode, an anode, CPL and at least one light emitting layer. In addition to these layers, it may also comprise further layers, for example in each case one or more hole-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, exciton-blocking layers, electron-blocking layers and/or charge-generating layers. An intermediate layer having, for example, an exciton blocking function can likewise be introduced between the two light-emitting layers. It should be noted, however, that not every one of these layers need be present. The organic electroluminescent element described herein may include one light emitting layer, or it may include a plurality of light emitting layers. That is, a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particularly preferred is a system with three light-emitting layers, wherein the three layers can display blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises a compound of the invention according to the invention.
Further, the organic electroluminescent element according to the present invention does not comprise a separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, i.e. the light emitting layer is directly adjacent to the hole injection layer or anode and/or the light emitting layer is directly adjacent to the electron transport layer or electron injection layer or cathode.
In the other layers of the organic electroluminescent element according to the invention, in particular in the hole-transport layer and in the light-emitting layer and in the CPL, all materials can be used in the manner customary in accordance with the prior art. The person skilled in the art will thus be able to use all materials known for organic electroluminescent elements in combination with the luminescent layer according to the invention without inventive effort.
The organic electroluminescent element of the present invention may be manufactured by forming an organic layer and an electrode using materials and methods well known in the art, in addition to one or more of the above organic layers including the above amino compound.
Further, a substance that can be used as an anode included in the organic electroluminescent element according to the present invention is not particularly limited, and vanadium, chromium, copper, zinc, and the like can be used as non-limiting examples, Metals such as gold and aluminum, or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDT), polypyrrole, and polyaniline; and carbon black, etc.
The substance that can be used as the cathode included in the organic electroluminescent element according to the present invention is not particularly limited, and as a non-limiting example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof can be used; liF/Al or Li 2 And multilayer structures such as O/Al.
The substrate to be used as the substrate included in the organic electroluminescent element of the present invention is not particularly limited, and silicon wafer, quartz, glass plate, metal plate, plastic film, sheet, or the like may be used as a non-limiting example.
Furthermore, preference is given to organic electroluminescent elements in which one or more layers can be applied by means of a sublimation process, wherein the sublimation process is carried out in a vacuum at a temperature of less than 10 -5 Pa, preferably below 10 -6 The material is applied by vapor deposition at an initial pressure of Pa. However, the initial pressure may also be even lower, for example below 10 -7 Pa。
Also preferred are organic electroluminescent elements in which one or more layers can also be applied by means of an organic vapor deposition process or by means of carrier gas sublimation, where at 10 -5 The material is applied at a pressure between Pa and 1 Pa. A particular example of this method is an organic vapor jet printing method, wherein the material is applied directly through a nozzle and is thus structured.
Furthermore, organic electroluminescent elements are preferred, from which one or more layers are produced, for example by spin coating, or by means of any desired printing method, for example screen printing, flexography, lithography, photoinitiated thermal imaging, thermal transfer, inkjet printing or nozzle printing. Soluble compounds the soluble compounds are obtained, for example, by suitable substitution of the compounds of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, a hybrid method is possible, in which one or more layers are applied, for example from a solution, and one or more further layers are applied by vapor deposition.
These methods are generally known to those of ordinary skill in the art and they can be applied to the organic electroluminescent element comprising the compound of the present invention without the inventive effort.
The invention therefore also relates to a method for manufacturing an organic electroluminescent element according to the invention, comprising applying at least one layer by means of a sublimation method, and/or applying at least one layer by means of an organic vapour deposition method or by means of carrier gas sublimation, and/or applying at least one layer from a solution by spin coating or by means of a printing method.
Furthermore, the present invention relates to a pharmaceutical composition comprising at least one compound of the invention as indicated above. The same preferable cases as indicated above with respect to the organic electroluminescent element apply to the compound of the present invention. In particular, the compounds may also preferably comprise other compounds. Treatment of the compounds of the invention from the liquid phase, for example by spin coating or by printing methods, requires treatment of preparations of the compounds of the invention, which preparations may be, for example, solutions, dispersions or emulsions. For this purpose, it may be preferable to use a mixture of two or more solvents. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchyl ketone, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylanisole, 3, 5-dimethylanisole, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decahydronaphthalene, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-cymene, phenetole, 1, 4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1-bis (3, 4-dimethylphenyl) ethane, or mixtures of these solvents.
Preferably, the organic layer includes a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a CPL layer, or an electron blocking layer.
Further, the hole transport layer, light emitting layer, or CPL layer comprises the amino compound of the present invention.
A consumer product made from the organic electroluminescent device, the consumer product comprising the organic electroluminescent device provided by the invention.
The consumer product described in the present invention may be one of the following products: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cellular telephones, tablet computers, tablet handsets, personal Digital Assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, micro-displays with a diagonal of less than 2 inches, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising a plurality of displays tiled together, theatre or gym screens, phototherapy devices, and billboards.
In addition, unless otherwise specified, all raw materials used in the present invention are commercially available, and any ranges recited in the present invention include any numerical value between the end values and any sub-range constituted by any numerical value between the end values or any numerical value between the end values.
The invention also relates to mixtures comprising at least one compound of formula (I) or a preferred embodiment described above and at least one further compound. If the compounds according to the invention are used as matrix materials, the other compounds may be fluorescent or phosphorescent emitters. The mixture may then additionally comprise other materials as additional matrix materials. The invention also relates to the use of the compounds according to the invention in electronic components. Preferably, as mentioned above and below, the compounds according to the invention are used in a hole transport layer or as host material in a light-emitting layer. The compounds according to the invention and the electronic components obtainable therefrom, in particular organic electroluminescent components, differ from the prior art in one or more of the following surprising advantages:
the amino compound of the invention has large plane conjugated benzo
Figure BDA0004140320760000111
The novel rigid structure, which is a compound represented by the general formula (I) of the present invention, has (1) a high carrier mobility; (2) high internal quantum efficiency; (3) stable film state; (4) The organic electroluminescent element of the present invention is suitable for use as a constituent material of a light-emitting layer of the organic electroluminescent element because of its excellent heat resistance.
In the organic electroluminescent element of the present invention using the amino compound represented by the general formula (I) as a host material for the light-emitting layer, since a compound having higher carrier mobility than conventional materials, high internal quantum efficiency, excellent amorphousness, and stable thin film state is used, it is possible to realize an organic electroluminescent element having high efficiency, low driving voltage, and long lifetime.
Further, in the present invention, the light-emitting layer is formed by the amino compound of the general formula (I), so that the high quantum efficiency performance and heat resistance of the compound can be utilized to the maximum extent, and the long-life organic electroluminescent element can be realized with higher efficiency.
In the present invention, the organic electroluminescent element of the present invention, in which the amino compound represented by the general formula (I) is used as a constituent material for at least one of the light-emitting layers or the laminated film in which two or more light-emitting layers are arranged, uses a compound having high carrier mobility, high internal quantum efficiency, excellent amorphism, and stable thin film state, and thus can realize a high-efficiency, low-driving voltage, and long-life organic electroluminescent element.
These advantages mentioned above are not accompanied by a weakening of other electronic properties.
It should be noted that variations of the embodiments described in the present invention fall within the scope of the present invention. Each feature disclosed in this disclosure may be replaced by alternative features serving the same, equivalent or similar purpose, unless expressly excluded. Thus, unless indicated otherwise, each feature disclosed in this document is to be understood as an example of a generic series or equivalent or similar feature.
All features of the invention may be combined with each other in any way, unless the specific features and/or steps are mutually exclusive. This applies in particular to the preferred features of the invention. Also, features that are not necessarily combined may be used alone (and not in combination). Furthermore, it should be noted that many features, particularly those of the preferred embodiments of the present invention, are inventive in their own right and should not be taken as part of an embodiment of the present invention. For these features, independent protection may be sought in addition to, or in lieu of, each of the presently claimed inventions.
The teachings of the technical actions disclosed in the present invention can be extracted and combined with other embodiments. The present invention is explained in more detail by the following examples, but is not intended to be limited thereby. Based on the description, one skilled in the art will be able to practice the invention throughout the scope of the disclosure and, without inventive effort, be able to prepare and use other compounds of the invention in electronic components or use the methods of the invention.
Drawings
In order to more clearly illustrate the embodiments of the invention or the technical solutions in the prior art, the drawings that are required in the embodiments or the description of the prior art will be briefly described, it being obvious that the drawings in the following description are only some embodiments of the invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
Fig. 1 shows a schematic diagram of an organic light emitting device 100. The illustrations are not necessarily drawn to scale. The device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. The device 100 may be fabricated by sequentially depositing the layers described.
Fig. 2 shows a schematic diagram of an organic light emitting device 200 with two light emitting layers. The device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first emissive layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second emissive layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 may be prepared by sequentially depositing the layers described. Because the most common OLED device has one light emitting layer, and device 200 has a first light emitting layer and a second light emitting layer, the light emitting peaks of the first and second light emitting layers may be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of the device 200, materials similar to those described with respect to the device 1 may be used. Fig. 2 provides one example of how some layers may be added from the structure of the device 100.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It will be apparent that the described embodiments are only some, but not all, embodiments of the invention. All other embodiments, based on the examples herein, which are within the scope of the invention as defined by the claims, will be within the scope of the invention as defined by the claims.
In the invention, the preparation methods are all conventional methods unless otherwise specified. All materials used, unless otherwise indicated, are commercially available from the disclosure and percentages such as percentages by mass unless otherwise indicated. The novel series of organic compounds provided by the present invention, all of which are carried out under well known suitable conditions, involve some simple organic preparation, for example the preparation of phenylboronic acid derivatives, can be synthesised by skilled operating skills and are not described in detail in the present invention.
Any range recited in the invention includes any numerical value between the endpoints and any sub-range of any numerical value between the endpoints or any numerical value between the endpoints.
The following examples are examples of the test apparatus and method for testing the performance of OLED materials and devices as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: photoresearch PR-715 was tested using a spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: using the NEWPORT 1931-C test;
life test: LTS-1004AC life test apparatus was used.
Example 1
A process for the preparation of compound B1012 comprising the steps of:
the first step: preparation of Compound Int-1
Figure BDA0004140320760000121
21.0mmol of 2-bromobiphenyl, 20.0mmol of p-chloroacetylene, 60mL of THF and 20mL of triethylamine are mixed under nitrogen protection, 4.0mmol of cuprous iodide and 4.0mmol of PdCl are added 2 (PPh 3 ) 2 The catalyst is heated to reflux and stirred for reaction for 10 hours, cooled to room temperature, concentrated and dried under reduced pressure, and separated and purified by a silica gel column to obtain a compound Int-1 as a yellow solid with yield: 76%.
And a second step of: preparation of Compound Int-2
Figure BDA0004140320760000122
Under the protection of nitrogen, 20.0mmol of Int-1 prepared in the previous step, 60.0mmol of copper bromide, 10.0mmol of anhydrous potassium phosphate and 60mL of nitromethane are mixed, the mixture is heated to reflux and stirred for reaction for 10 hours, cooled to room temperature, filtered, concentrated and dried under reduced pressure, and the compound Int-2 is obtained by separating and purifying with a silica gel column, and the yield is 92%.
And a third step of: preparation of Compound Int-3
Figure BDA0004140320760000131
Referring to the synthesis method of the first step, 2-bromobiphenyl is replaced by Int-2, p-chloroacetylene is replaced by trimethylsilylacetylene, and the compound Int-3 is prepared with a yield of 74%.
Fourth step: preparation of Compound Int-4
Figure BDA0004140320760000132
Under the protection of nitrogen, 20.0mmol of Int-3 prepared in the previous step and 80mL of 30% sodium methoxide methanol solution are heated to reflux and stirred for reaction for 5 hours, cooled to room temperature, concentrated to dryness under reduced pressure, dissolved with dichloromethane, washed twice with water, and the organic phase is collected, dried, filtered, concentrated to dryness under reduced pressure, and separated and purified by a silica gel column to obtain the compound Int-4 as a yellow solid with the yield of 85%.
Fifth step: preparation of Compound Int-5
Figure BDA0004140320760000133
Under the protection of nitrogen, 20.0mmol of Int-4 prepared in the previous step and 60mL of dichloromethane are mixed, 30.0mmol of trifluoromethanesulfonic acid is added dropwise, stirring reaction is carried out at room temperature for 12 hours, 50mL of saturated sodium bicarbonate aqueous solution is added, an organic phase is separated, dried, filtered, filtrate is concentrated and dried under reduced pressure, and compound Int-5 is obtained by separation and purification through a silica gel column, and a white solid is obtained with the yield of 94%.
Sixth step: preparation of Compound B1012
Figure BDA0004140320760000134
22.0mmol of Int-5 prepared in the previous step and 20.0mmol of N- ([ 1,1' -biphenyl) under the protection of nitrogen ]-4-yl) dibenzo [ b, d]Furan-2-amine, 30.0mmol of sodium tert-butoxide, 2.0mmol of cuprous iodide, 0.2mmol of Pd 2 (dba) 3 Mixing with 0.5mmol of 10% tri-tert-butylphosphine toluene solution, adding 80mL of dimethylbenzene, heating to 110 ℃, stirring for reaction for 15 hours, cooling to room temperature, adding 50mL of water, separating out an organic phase, extracting the aqueous phase with toluene, drying the organic phase, filtering, concentrating the filtrate under reduced pressure, and separating and purifying with a silica gel column to obtain a compound B1012, yellow solid with a yield of 83%, and MS (TOF): m/z 612.2343[ M+H ]] + 。
Example 2
Preparation of compound B1034, comprising the steps of:
the first step: preparation of Compound Int-6
Figure BDA0004140320760000141
Referring to the synthesis of the first step of example 1, the compound Int-6 was prepared in 75% yield by substituting 2-bromobiphenyl of the first step of example 1 with 4-chloro-2-phenylbromobenzene and p-chloroacetylene with phenylacetylene.
And a second step of: preparation of Compound Int-7
Figure BDA0004140320760000142
Referring to the synthesis method of the second step of example 1, only the Int-1 of the second step of example 1 was replaced with Int-6 to prepare the compound Int-7 in a yield of 90%.
And a third step of: preparation of Compound Int-8
Figure BDA0004140320760000143
Referring to the synthesis of the first step of example 1, the compound Int-8 was prepared in 75% yield by substituting Int-7 for 2-bromobiphenyl and substituting trimethylsilylaletylene for p-chloroacetylene of the first step of example 1.
Fourth step: preparation of Compound Int-9
Figure BDA0004140320760000144
Referring to the synthesis method of the fourth step of example 1, only the Int-3 of the fourth step of example 1 was replaced with Int-8 to prepare the compound Int-9 in 88% yield.
Fifth step: preparation of Compound Int-10
Figure BDA0004140320760000145
Referring to the synthesis method of the fifth step of example 1, only the Int-4 of the fifth step of example 1 was replaced with Int-9 to prepare the compound Int-10 in a yield of 87%.
Sixth step: preparation of Compound B1034
Figure BDA0004140320760000151
21.0mmol of Int-10 prepared in the previous step, 20.0mmol of biphenyl benzidine, 30.0mmol of sodium tert-butoxide, 2.0mmol of cuprous iodide and 0.2mmol of Pd under the protection of nitrogen 2 (dba) 3 Mixing with 0.4mmol of 10% tri-tert-butylphosphine toluene solution, adding 80mL of dimethylbenzene, heating to 110 ℃, stirring for reaction for 15 hours, cooling to room temperature, adding 50mL of water, separating out an organic phase, extracting the aqueous phase with toluene, drying the organic phase, filtering, concentrating the filtrate under reduced pressure, and separating and purifying with a silica gel column to obtain a compound B1034, a yellow solid with a yield of 78%, and MS (TOF): m/z598.2551[M+H] + 。
Example 3
The preparation of compound B1077, comprising the steps of:
the first step: preparation of Compound Int-11
Figure BDA0004140320760000152
Referring to the synthesis of the first step of example 1, the compound Int-11 was prepared in 77% yield by replacing only the p-chloroacetylene of the first step of example 1 with phenylacetylene.
And a second step of: preparation of Compound Int-12
Figure BDA0004140320760000153
Referring to the synthesis method of the second step of example 1, only Int-1 of the second step of example 1 was replaced with Int-11 to prepare compound Int-12 in 93% yield.
And a third step of: preparation of Compound Int-13
Figure BDA0004140320760000154
Referring to the synthesis of the first step of example 1, substitution of 2-bromobiphenyl of the first step of example 1 for Int-12 and substitution of p-chloroacetylene for phenylacetylene produced compound Int-13 in a yield of 76%.
Fourth step: preparation of Compound Int-14
Figure BDA0004140320760000155
Referring to the synthesis method of the second step of example 1, only the second step of example 1 was replaced with Int-13 to prepare compound Int-14 in 92% yield.
Fifth step: preparation of Compound B1077
Figure BDA0004140320760000161
10.0mmol of Int-14 prepared in the previous step, 12.0mmol of (3- (9-phenyl-carbazol-3-yl) phenyl) boric acid, 30.0mmol of anhydrous sodium carbonate and 0.1mmol of Pd (PPh) under the protection of nitrogen 3 ) 4 Mixing, adding 40mL of toluene, 20mL of ethanol and 20mL of water, heating to reflux, stirring, reacting for 10 hours, cooling to room temperature, adding 50mL of water, separating an organic phase, extracting the aqueous phase with toluene, drying the organic phase, filtering, concentrating the filtrate under reduced pressure, and separating and purifying with a silica gel column to obtain a compound B1077, yellow solid with a yield of 76%, MS (TOF): m/z 672.2705[ M+H ] ] + 。
Referring to the synthesis procedure analogous to the above examples, the following compounds were prepared:
Figure BDA0004140320760000162
/>
Figure BDA0004140320760000171
/>
Figure BDA0004140320760000181
/>
Figure BDA0004140320760000191
/>
Figure BDA0004140320760000201
example 4
An OLED device 100, as shown in FIG. 1, comprises a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111
The preparation method of the OLED element (without the hole blocking layer) comprises the following steps:
1) The glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, rinsed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dried, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
2) Placing the above ITO glass substrate in vacuum chamber, and vacuumizing to less than 1×10 -5 Pa, evaporating metallic silver as anode on the ITO film, and evaporating film thickness to be
Figure BDA0004140320760000202
Continuing to vapor deposit the compounds DNTPD and F4TCNQ respectively as hole injection layers, wherein F4TCNQ is 3% of DNTPD by mass, and the vapor deposition film thickness is +.>
Figure BDA0004140320760000203
/>
3) Continuously evaporating a layer of the compound shown in the formula I as a hole transport layer on the hole injection layer film, wherein the evaporation film thickness is
Figure BDA0004140320760000204
4) Continuously evaporating a layer of compound HT202 as electron blocking layer on the hole transport layer to obtain an evaporating film with a thickness of
Figure BDA0004140320760000205
5) Continuously evaporating a layer of compound BH345 and BD035 on the electron blocking layer as an organic light-emitting layer, wherein BD035 is a doping material and the compound BH345 is a main material, the doping concentration of the compound BD035 in BH345 is 10%, and the evaporating film thickness is
Figure BDA0004140320760000211
6) And then on the light-emitting layerContinuing to vapor deposit a layer of compound LiQ and ET212 as electron transport layers of the device, wherein the mass ratio of the LiQ to the ET212 is 1:1, and the vapor deposition film thickness is
Figure BDA0004140320760000218
7) Evaporating a layer of compound LiF on the electron transport layer to obtain an electron injection layer with a thickness of
Figure BDA0004140320760000212
8) Evaporating metal magnesium and silver on the electron injection layer to form a cathode layer of the element, wherein the mass ratio of magnesium to silver is 1:10, and the film thickness of the evaporated film is
Figure BDA0004140320760000213
Finally, the compound same as the compound in the step 3) is deposited on the cathode layer as a capping layer of the element, and the thickness of the deposited film is
Figure BDA0004140320760000214
The structure of the compound used in example 4 above is as follows:
Figure BDA0004140320760000215
as shown in fig. 2, the organic light emitting device 200 includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first light emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213.
Comparative example 1
Example 4 the same procedure is followed except that compound H01 is used in place of the compound of formula (I) in example 4, step 3) and the final capping layer. The structure of compound H01 is:
Figure BDA0004140320760000216
comparative example 2
Example 4 the same procedure is followed except that compound H02 is used instead of the compound of formula (I) in example 4, step 3) and the final capping layer. The structure of compound H02 is:
Figure BDA0004140320760000217
the driving voltage and current efficiency of the organic electroluminescent elements prepared in example 4 and comparative examples 1 and 2 and the lifetime of the elements were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the luminance of the organic electroluminescent element was measured to reach 1000cd/m by increasing the voltage at a rate of 0.1V per second 2 The voltage at the time is the driving voltage, and the current density at the time is measured; the ratio of brightness to current density is the current efficiency; LT90% life test is as follows: at 1000cd/m using a luminance meter 2 The luminance decay of the organic electroluminescent element was measured to be 900cd/m while maintaining a constant current at luminance 2 Time in hours. All results are summarized in table 1, and test results were normalized against the data of comparative example 1 (bracketed data) for comparison.
TABLE 1 results of testing the performance of the elements
Figure BDA0004140320760000221
/>
Figure BDA0004140320760000231
As can be seen from table 1, the compound of the present invention provides an organic electroluminescent element having high efficiency and long lifetime as a material for a hole transport layer and a capping layer, and the element has low driving voltage, improved current efficiency, and excellent performance in terms of LT90% lifetime.
The compound H01 of comparative example 1 is different from the compound of the present invention in that the plane conjugate area of H01 is large, the hole transport ability is weaker than the electron transport ability, the transport of excitons in the element is unbalanced, the element driving voltage is increased, and the efficiency is lowered. The compound of the invention has small plane conjugation area and improves hole transmission capability, so that the compound has excellent performance in molecular film formation and exciton transmission, the exciton transmission in the element is more balanced, and the element performance is improved.
The compound H02 in comparative example 2 is different from the compound of the present invention in that H02 contains two para-arylamine groups, which has a large steric hindrance and is unfavorable for the close packing of molecules, while the compound of the present invention contains one arylamine group, which has a small steric hindrance, so that the performance of the compound in molecular film formation and exciton transmission is more excellent, the exciton transmission in the element is more balanced, and the element performance is improved.
The organic electroluminescent device of the present invention can be applied to flat-panel light emitters such as wall-mounted televisions, flat-panel displays, and lighting, light sources such as copiers, printers, backlights for liquid crystal displays, and measuring instruments, display panels, and marker lamps.
The foregoing is merely illustrative of the present invention, and the present invention is not limited thereto, and any person skilled in the art will readily recognize that variations or substitutions are within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.

Claims (10)

1. An amino compound is characterized in that the structural general formula of the amino compound is shown as a formula (I):
Figure FDA0004140320750000011
wherein X is 1 、X 2 、X 3 、X 4 Each independently selected from N or CR 5 Or any two adjacent X 1 And X 2 、X 2 And X 3 、X 3 And X 4 Represents a group represented by formula (II) or formula (III);
Figure FDA0004140320750000012
z represents CR 6 Or N; and two adjacent "≡" groups are indicated for the adjacent groups X in formula (I) 1 And X 2 、X 2 And X 3 、X 3 And X 4 ；
G represents O, S, se, CR 7 R 8 、SiR 7 R 8 Or NR (NR) 9 ；
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 Are identical to or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 ～C 30 Alkyl, substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 3 ～C 30 Cycloalkyl, substituted or unsubstituted C 2 ～C 50 Heteroaryl, substituted or unsubstituted C 1 ～C 30 Alkoxy, substituted or unsubstituted C 6 ～C 50 Aryloxy, substituted or unsubstituted C 1 ～C 30 Alkylthio, substituted or unsubstituted C 5 ～C 50 Arylthio, substituted or unsubstituted C 1 ～C 30 Alkylamino, substituted or unsubstituted C 5 ～C 50 Arylamine group, substituted or unsubstituted C 1 ～C 30 Alkylsilyl, substituted or unsubstituted C 5 ～C 50 Arylsilyl, cyano, halogen or a group of formula (IV), any adjacent two or more R 1 ～R 9 Can be optionally joined or fused to form a substituted or unsubstituted ring with or without heteroatoms N, O, S, P,B. Si or Se, and at R 1 ～R 6 One of them is a group represented by the formula (IV);
Figure FDA0004140320750000021
l is selected from single bond, substituted or unsubstituted C 6 ～C 50 Arylene, substituted or unsubstituted C 2 ～C 50 A group consisting of heteroarylenes;
m is selected from integers of 0 to 5;
Ar 1 、Ar 2 each independently selected from the group consisting of substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 5 ～C 50 Arylamine group, substituted or unsubstituted C 6 ～C 50 Condensed aryl, substituted or unsubstituted C 2 ～C 50 Heteroaryl groups;
the dotted line represents the attachment site of the group;
R 3 、R 4 respectively representing one or more to saturated substitutions.
2. The amino compound of claim 1, wherein the amino compound is selected from the group consisting of the structures shown below:
Figure FDA0004140320750000022
Figure FDA0004140320750000031
wherein R is 1 ～R 6 、G、L、m、Ar 1 And Ar is a group 2 The definition of (a) is the same as that of formula (I).
3. An amino compound according to claim 1, characterized in thatWherein R is as follows 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, isopropyl, isobutyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenyl
Figure FDA0004140320750000033
A group selected from the group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, and a group represented by formula (IV), and wherein R 1 ～R 6 One of them is a group represented by the formula (IV);
Figure FDA0004140320750000032
/>
R 7 、R 8 each occurrence is independently selected from the group consisting of hydrogen, deuterium, methyl, substituted or unsubstituted phenyl, substituted or unsubstituted fluorenyl;
R 9 at each occurrence is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenyl
Figure FDA0004140320750000034
A group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group;
m is selected from 0, 1 or 2;
Ar 1 、Ar 2 each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenyl
Figure FDA0004140320750000042
A group consisting of a group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group;
the dotted line represents the attachment site of the group.
4. The amino compound of claim 1, wherein R 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently selected from the group consisting of hydrogen, deuterium, tert-butyl, substituted or unsubstituted phenyl, or formula (IV), and at R 1 ～R 6 One of them is a group represented by the formula (IV);
R 7 、R 8 each occurrence is independently selected from the group consisting of methyl, substituted or unsubstituted phenyl, substituted or unsubstitutedA group consisting of fluorenyl groups;
R 9 at each occurrence selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene.
5. The amino compound of any one of claims 1 to 4, wherein L is selected from a single bond or a group consisting of the following groups III-1 to III-24:
Figure FDA0004140320750000041
/>
Figure FDA0004140320750000051
Wherein X is selected from O, S, se, CR ' R ', siR ' R ' or NAr ';
Z 11 、Z 12 、Z 13 、Z 14 each independently selected from the group consisting of hydrogen, deuterium, halogen atoms, hydroxyl, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1 -C 60 Alkyl, C of (2) 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Is C 3 -C 60 Cyclic olefin group, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Aryl sulfide group, or substituted or unsubstituted C 2 -C 60 Heteroaryl groups;
y1 represents an integer of 1 to 4; y2 represents an integer of 1 to 6; y3 represents an integer of 1 to 3; y4 represents an integer of 1 to 5; y5 represents an integer of 1 or 2;
r ', R' are each independently selected from C 1 -C 60 Alkyl, C of (2) 1 -C 60 Is optionally substituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 Heteroaryl, R' and R "may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the ring formed; preferably, R', R "is methyl, phenyl or fluorenyl;
Ar' is selected from C 1 -C 60 Alkyl, C of (2) 1 -C 60 Heteroalkyl of (C) 3 -C 60 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamine groups, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups; preferably, ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;
wherein the dotted line represents the attachment site of the group.
6. The amino compound of any one of claims 1-5, wherein the amino compound is selected from the group consisting of structures represented by B1007-B1090:
Figure FDA0004140320750000061
/>
Figure FDA0004140320750000071
/>
Figure FDA0004140320750000081
/>
Figure FDA0004140320750000091
7. an organic electroluminescent material, characterized in that it comprises an amino compound according to any one of claims 1 to 6.
8. An organic electroluminescent device comprising a first electrode, a second electrode, a capping layer, and at least one organic layer disposed between the first electrode and the second electrode, wherein the organic layer or capping layer comprises the amino compound of any one of claims 1-6.
9. The organic electroluminescent device according to claim 8, wherein the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer; wherein the organic layer is one layer, two layers or multiple layers; the amino compound is in the hole transport layer, the light emitting layer or the capping layer.
10. A consumer product comprising the organic electroluminescent device of any one of claims 8-9.
CN202310287497.9A 2023-03-17 2023-03-17 Amino compound and application thereof Pending CN116239479A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117645592A (en) * 2024-01-29 2024-03-05 广东阿格蕾雅光电材料有限公司 Compound and organic electroluminescent device
WO2024085607A1 (en) * 2022-10-17 2024-04-25 주식회사 엘지화학 Novel compound and organic light-emitting device comprising same

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024085607A1 (en) * 2022-10-17 2024-04-25 주식회사 엘지화학 Novel compound and organic light-emitting device comprising same
CN117645592A (en) * 2024-01-29 2024-03-05 广东阿格蕾雅光电材料有限公司 Compound and organic electroluminescent device

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