CN116535419A - Amino compound, organic electroluminescent element and organic electroluminescent device - Google Patents

Amino compound, organic electroluminescent element and organic electroluminescent device Download PDF

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CN116535419A
CN116535419A CN202310526311.0A CN202310526311A CN116535419A CN 116535419 A CN116535419 A CN 116535419A CN 202310526311 A CN202310526311 A CN 202310526311A CN 116535419 A CN116535419 A CN 116535419A
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amino compound
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曹建华
唐伟
邸庆童
张昊
边坤
刘殿君
郭文龙
李程辉
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Beijing Bayi Space LCD Technology Co Ltd
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Beijing Bayi Space LCD Technology Co Ltd
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Abstract

The present invention relates to an amino compound, an organic electroluminescent element, and an organic electroluminescent device having improved driving voltage and/or current efficiency characteristics can be provided by including the amino compound according to the present disclosure.

Description

Amino compound, organic electroluminescent element and organic electroluminescent device
Technical Field
The invention belongs to the technical field of organic electroluminescence, and particularly relates to an amino compound and application thereof in an organic electroluminescent element and an organic electroluminescent device.
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 present disclosure is directed to an amino compound, an organic electroluminescent material, a light-emitting element, and a light-emitting device 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):
wherein two adjacent W 1 And W is 2 A group of formula (II) or formula (III); two adjacent X' s 1 And X 2 A group of formula (IV);
g is selected from O, S, CR 3 R 4 、SiR 3 R 4 Or NAr 5 The method comprises the steps of carrying out a first treatment on the surface of the Formula (II) and formula (III)Wherein two adjacent "≡" are each two adjacent groups W in formula (I) 1 And W is 2 Two adjacent "≡" in formula (IV) indicate two adjacent groups X in formula (I) 1 And X 2 ；
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 Are identical to or different from each other and are each independently selected from hydrogen, deuterium, cyano, halogen atoms, 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 Aryl silyl group, any adjacent two or more R 1 、R 2 Optionally bonded 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;
L 1 selected from single bonds, 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 、Ar 3 、Ar 4 、Ar 5 each independently selected from the group consisting of substituted or unsubstituted C 6 ～C 50 Aryl, substituted or unsubstituted C 5 ～C 50 Arylamine groups, substituted or unsubstitutedC of (2) 6 ～C 50 Condensed aryl, substituted or unsubstituted C 2 ～C 50 Heteroaryl groups.
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,A group, perylene group, fluoranthenyl group, naphthacene group, pentacene group, benzopyrene group, biphenyl group, terphenyl group, tripolyphenyl group, tetrabiphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthrene group, triphenylene group, dihydropyrenyl group, tetrahydropyrenyl group, cis-or trans-indenofluorenyl group, cis-or trans-indenocarbazolyl group, indolocarbazolyl group, benzofuranocarbazolyl group, benzothiophenocarbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, 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, naphthamidazolyl, phenanthroimidazolylPyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthazolyl, anthracoxazolyl, phenanthrooxazolyl, isoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazabenzophenanthryl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthryl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, rubrene, erythronyl naphthyridinyl, azacarbazolyl, benzocarbolinyl, carbolinyl, phenanthrolinyl, 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, pteridinyl, indolizinyl, quinazolinyl, benzothiadiazolyl, or a combination of groups derived from these groups.
"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 following structures:
wherein the symbols used are as defined above.
Further, the G is selected from O, S or NAr 5 The method comprises the steps of carrying out a first treatment on the surface of the Further, m is 0, 1 or 2.
Further, the R 1 ～R 6 Each independently selected from the group consisting of hydrogen, deuterium, nitrile, methyl, ethyl, isopropyl, isobutyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetrabiphenylPhenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracyl, substituted or unsubstituted benzanthraceyl, substituted or unsubstituted pyrenyl, substituted or unsubstitutedA 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, and a substituted or unsubstituted dibenzothiophenyl group.
Further, the Ar 1 ～Ar 5 Each independently selected from the group consisting of: phenyl, naphthyl, anthryl, benzanthraceyl, phenanthryl, pyrenyl,A group, perylene group, fluoranthenyl group, naphthacene group, pentacene group, benzopyrene group, biphenyl group, terphenyl group, tripolyphenyl group, tetrabiphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthrene group, triphenylene group, dihydropyrenyl group, tetrahydropyrenyl group, cis-or trans-indenofluorenyl group, cis-or trans-indenocarbazolyl group, indolocarbazolyl group, benzofuranocarbazolyl group, benzothiophenocarbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, 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, naphthamidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxaline A benzoimidazolyl group, an oxazolyl group, a benzoxazolyl group, a naphthooxazolyl group, an anthracoxazolyl group, a phenanthrooxazolyl group, an isoxazolyl group, a 1, 2-thiazolyl group, a 1, 3-thiazolyl group, a benzothiazolyl group, a pyridazinyl group, a hexaazabenzophenanthryl group, a benzopyridazinyl group, a pyrimidinyl group, a benzopyrimidinyl group, a 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, benzocarbolinyl, carbolinyl, phenanthrolinyl, 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, pteridinyl, indolizinyl, quinazolinyl, benzothiadiazolyl, or groups derived from combinations of these systems.
According to an embodiment of the invention, the R 1 ～R 6 Each independently selected from the group consisting of hydrogen, deuterium, t-butyl, substituted or unsubstituted phenyl.
According to an embodiment of the invention, the Ar 1 ～Ar 5 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 pyrenylA 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 groupUnsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.
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 according to the 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 means a silane group substituted with at least one aryl group having 6 to 60 carbon atoms, and examples of the aryl group include phenyl dimethylsilyl group, naphthyl dimethylsilyl group, phenyl diethylsilicon group, diphenylmethylsilicon group, diphenylethylsilicon group, and triphenylsilicon group.
The alkylamino group used in the present invention means an amino group substituted with an alkyl group having 1 to 40 carbon atoms or an amino group substituted with two alkyl groups having 1 to 40 carbon atoms, and as non-limiting examples of the alkylamino group, there are methylamino group, dimethylamino group, ethylamino group, diethylamino group and the like.
As the arylamino group used in the present invention, an amino group substituted with an aryl group having 6 to 60 carbon atoms or an swollen amino group substituted with two aryl groups having 6 to 60 carbon atoms is mentioned, and as a non-limiting example of the arylamino group, an anilino group, a diphenylamino group, a 1-naphthylamino group, a 2-naphthylamino group, an N-phenylnaphthalen-1-amino group, a carbazolyl group, a phenoxazinyl group and the like are mentioned.
"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.
Substituted alkyl, substituted aryl, take as described in the present inventionThe substituents of the substituted heteroaryl, substituted arylamine, substituted fused aryl, substituted arylene, substituted heteroarylene 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 N and Ar according to the foregoing 3 、Ar 4 Connection, preferably, the L 1 Selected from a single bond or a group consisting of groups III-1 to III-24:
wherein T is 3 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 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' 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.
Preferably, the L 1 Selected from a single bond or a group consisting of the following groups III-1 to III-15, III-24:
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 C01-C210 structures:
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wherein each x— is independently selected from one of the following structures:
* -and- (x) represents a bond.
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.
In addition to one or more of the organic layers containing the above amino compound, the organic layer and the electrode may be formed by materials and methods known in the art.
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 as a non-limiting example, metals such as vanadium, chromium, copper, zinc, gold, aluminum, or the like, or alloys thereof can be used; 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 substance that can be used as the substrate included in the organic electroluminescent element according to the present invention is not particularly limited, and as a non-limiting example, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, a sheet, or the like can be used.
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 according to the present invention without inventive effort.
The invention therefore also relates to a method of 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 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 furthermore preferably comprise further 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 comprises 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 has novel rigid structures such as large-plane conjugated imidazo benzofuran, imidazo benzothiophene, pyrazino benzofuran or pyrazino benzothiophene, and the like, and the compound represented by the general formula (I) has large mobility of (1) carriers; (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 device 200, materials similar to those described with respect to device 100 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 C19 comprising the steps of:
the first step: preparation of compound int.—1
Under the protection of nitrogen, 37.8mmol of trimethylsilyl acetylene is dissolved in 50mL of triethylamine, 45.5mmol of 3-bromo-2-cyanobenzothiophene, 4.0mmol of cuprous iodide, 4.0mmol of palladium acetate and 8.0mmol of DPEPhos (bis (2-diphenylphosphinophenyl) ether) are added, the mixture is heated, refluxed and stirred for reaction for 6 hours, concentrated and dried under reduced pressure, and the mixture is separated and purified by a silica gel column to obtain an intermediate Int. -1, and the yield is 84%.
And a second step of: preparation of compound int-2
Under the protection of nitrogen, mixing 20.0mmol of Int.-1 prepared in the previous step, 40.0mmol of nitromethane, 40.0mmol of potassium hydroxide and 50mL of DMSO, heating to 110 ℃, stirring and reacting for 45 minutes, cooling to room temperature, pouring the reaction solution into 150mL of ice water, filtering, washing a filter cake with water, and recrystallizing with methanol to obtain a compound Int.-2 as a yellow solid with a yield of 92%.
And a third step of: preparation of compound int.—3
20.0mmol of int.-2 prepared in the previous step, 40.0mmol of triethylamine and 80mL of dichloromethane are mixed, cooled to 0 ℃, 24.0mmol of benzoyl chloride is added dropwise, the mixture is stirred and reacted for 30 minutes, the mixture is warmed to room temperature and stirred and reacted for 2 hours, 50mL of water is added, an organic phase is separated, washed with water, the organic phase is dried, filtered, and the filtrate is concentrated and dried under reduced pressure to obtain a compound int.-3 as a yellow solid, and the yield is 100%.
Fourth step: preparation of compound int.—4
20.0mmol of int.—3 prepared in the previous step, 100mL of methanol and 50mL of water are mixed, 0.1mol of ammonium chloride and 0.1mol of iron powder are added, the mixture is stirred at room temperature for reaction for 15 hours, the mixture is filtered, the filtrate is concentrated to dryness under reduced pressure, the residue is dissolved by methylene dichloride, the filtrate is filtered, the filtrate is washed twice with water, the organic phase is collected, dried, filtered, and the filtrate is concentrated to dryness under reduced pressure to obtain a compound int.—4 as a yellow solid with a yield of 90%.
Fifth step: preparation of compound int.—5
Under the protection of nitrogen, 20.0mmol of Int. -4 prepared in the previous step and 60mL of toluene are mixed, 22.0mmol of iodobenzene, 80.0mmol of anhydrous potassium carbonate, 2.0mmol of cuprous iodide and 5.0mmol of N, N' -dimethylethylenediamine are added, the mixture is heated to reflux and stirred for reaction for 12 hours, the temperature is reduced to room temperature, the mixture is filtered, the filtrate is concentrated and dried under reduced pressure, and the compound Int. -5, yellow solid and the yield of 84% are obtained through separation and purification by a silica gel column.
Sixth step: preparation of compound int.—6
Under the protection of nitrogen, 20.0mmol of Int.-5 prepared in the previous step is dissolved in 80mL of toluene, 0.2mmol of p-toluenesulfonic acid is added, the temperature is raised to reflux, the mixture is stirred and reacts for 12 hours, the temperature is reduced to room temperature, 50mL of water is added, an organic phase is separated, the mixture is concentrated and dried under reduced pressure, and the compound Int.-6 is obtained by separating and purifying with a silica gel column, and is a white solid with the yield of 93%.
Seventh step: preparation of compound int-7
Under the protection of nitrogen, 20.0mmol of Int.-6 prepared in the previous step is dissolved in 50mL of DMF, the temperature is reduced to 0 ℃, 21.0mmol of NBS is added in portions, the reaction is stirred for 2 hours, the reaction solution is poured into 150mL of saturated sodium chloride aqueous solution, the solution is filtered, a filter cake is washed with water, and the solid is separated and purified by a silica gel column to obtain the compound Int.-7, white solid, and the yield is 90%.
Eighth step: preparation of Compound C19
22.0mmol of Int.- -7 (reactant 1), 20.0mmol of sub-1 (reactant 2), 30.0mmol of sodium tert-butoxide and 0.2mmol of Pd prepared in the previous step under the protection of nitrogen 2 (dba) 3 And 0.4mmol Xantphos, then 80mL of toluene is added, the temperature is raised to 100 ℃ and the mixture is stirred for reaction for 15 hours, the temperature is reduced to room temperature, 50mL of water is added, the organic phase is separated, the water phase is extracted by toluene, the organic phase is dried and filtered, the filtrate is concentrated and dried under reduced pressure, and the compound C19 is obtained by separating and purifying by a silica gel column;
X＝CPh 2 Yellow solid, yield 84%, MS (TOF): m/z 860.3113[ M+H ]] + ； 1 HNMR(δ、CDCl 3 )：8.13～8.12(1H,d)；8.04～7.98(2H,m)；7.91～7.84(2H,m)；7.69(1H,s)；7.63～7.55(6H,m)；7.53～7.45(7H,m)；7.42～7.33(8H,m)；7.25～7.18(3H,m)；7.15～7.06(5H,m)；7.02～6.97(2H,m)；6.95～6.89(4H,m)。
X=o, yellow solid, yield 85%, MS (TOF): m/z 710.2274[ M+H ]] + ； 1 HNMR(δ、CDCl 3 )：8.13～8.12(1H,d)；8.04～7.98(2H,m)；7.91～7.88(1H,d)；7.75～7.72(2H,m)；7.63～7.57(5H,m)；7.55～7.45(6H,m)；7.42～7.32(8H,m)；7.25～7.20(2H,m)；6.97～6.91(3H,m)；6.88～6.86(1H,d)。
Referring to the synthesis procedure analogous to the above examples, the following compounds were prepared:
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example 2
A process for the preparation of compound C113 comprising the steps of:
the first step: preparation of compound int.—8
Referring to the synthetic method of example 1, compound int.—8 was prepared in 89% yield by replacing only the 3-bromo-2-cyanobenzothiophene of the first step of example 1 with 2-iodo-3-cyanobenzothiophene.
And a second step of: preparation of compound int.—9
Referring to the synthetic method of example 1, compound int.—9 was prepared in 92% yield by replacing only int.—1 of the second step of example 1 with int.—8.
And a third step of: preparation of compound int.—10
20.0mmol of int..about.9 prepared in the previous step was dissolved in 100mL of methanol, 0.2g of 10% palladium on carbon was added, hydrogen was introduced at room temperature and normal pressure, the reaction was stirred for 12 hours, filtration, and the filtrate was concentrated under reduced pressure and dried to give compound int..about.10 as a brown solid in 100% yield.
Fourth step: preparation of compound int.—11
Under the protection of nitrogen, 20.0mmol of Int. -10 and 20.0mmol of diphenylethanedione prepared in the previous step are dissolved in 80mL of toluene, 0.2mmol of p-toluenesulfonic acid is added, the temperature is raised to reflux, the reaction is stirred for 12 hours, the temperature is reduced to room temperature, 50mL of water is added, an organic phase is separated, the organic phase is concentrated and dried under reduced pressure, and the compound Int. -11, yellow solid and the yield of 90% are obtained through separation and purification by a silica gel column.
Fifth step: preparation of compound int.—12
Referring to the synthetic method of example 1, compound int.—12 was prepared in 93% yield as yellow solid by replacing only int.—6 of the seventh step of example 1 with int.—11.
Sixth step: preparation of Compound C113
22.0mmol of Int.-12 (reactant 1), 20.0mmol of sub-2 (reactant 2), 30.0mmol of sodium tert-butoxide and 0.2mmol of Pd prepared in the previous step under the protection of nitrogen 2 (dba) 3 And 0.4mmol of 10% tri-tert-butyl phosphorus toluene solution, then 80mL of toluene is added, the temperature is raised to 100 ℃ and the stirring reaction is carried out for 15 hours, the temperature is reduced to room temperature, 50mL of water is added, the organic phase is separated, the water phase is extracted by toluene, the organic phase is dried, filtered, the filtrate is concentrated to dryness under reduced pressure, and the compound C113 is obtained by separating and purifying by a silica gel column, the yield is 83 percent, and MS (TOF): m/z 706.2255[ M+H ]] + ； 1 HNMR(δ、CDCl 3 )：9.07(1H,s)；8.70(1H,s)；8.31～8.28(1H,m)；8.05～7.97(5H,m)；7.94(1H,s)；7.83～7.82(1H,d)；7.69～7.62(5H,m)；7.60～7.52(6H,m)；7.40～7.38(1H,d)；7.32～7.25(4H,m)；7.23～7.19(2H,m)；7.06～7.01(2H,m)；6.98～6.95(1H,m)。
Referring to the synthesis procedure analogous to the above examples, the following compounds were prepared:
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in the above embodiments, each x— is independently selected from one of the structures shown below:
* -and- (x) represents a bond.
Example 3
As shown in fig. 1, an OLED element 100 of the present embodiment is a top emission light element, and includes a substrate 101, an anode layer 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode layer 102, a hole transport layer 104 disposed on the hole injection layer 103, an electron blocking layer 105 disposed on the hole transport layer 104, an organic light emitting layer 106 disposed on the electron blocking layer 105, a hole blocking layer 107 disposed on the organic light emitting layer 106, an electron transport layer 108 disposed on the hole blocking layer 107, an electron injection layer 109 disposed on the electron transport layer 108, and a cathode 110 disposed on the electron injection layer 109 and a capping layer 111 disposed on the cathode, wherein the method for manufacturing the OLED element excluding the hole blocking layer 107 includes 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) Handle upperPlacing the processed ITO glass substrate in a vacuum cavity, and vacuumizing to less than 1×10 -5 Pa, depositing metallic silver as an anode layer on the ITO film, the thickness of the deposited film beingContinuing to vapor deposit the compounds HI01 and HI02 as hole injection layers respectively, wherein HI02 is 3% of HI01 by mass, and the vapor deposition film thickness is +.>
3) Continuously evaporating compound HTM as hole transport layer on the hole injection layer to obtain an evaporating film with a thickness of
4) Continuously evaporating a compound HT022 as an electron blocking layer on the hole transport layer, wherein the evaporating film thickness is as follows
5) The compound shown in the formula (I) and RH01 are continuously evaporated on the electron blocking layer as main materials, and RD030 is used as doping material, wherein the mass ratio of the compound shown in the formula (I) and RH01 is 1:1, the RD030 is 5% of the mass of the main materials, the organic light-emitting layer is used as an element, and the film thickness of the organic light-emitting layer obtained by evaporation is
6) Continuously evaporating a layer of LiQ and a compound ET033 on the organic light-emitting layer as an electron transport layer of the element, wherein the compound ET033 is 40% of the mass of LiQ, and the evaporating film thickness is
7) Continuously evaporating a LiF layer on the electron transport layer to form an electron injection layer with an evaporating film thickness of
8) Evaporating metal magnesium and silver on the electron injection layer to form a transparent 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
9) Evaporating a CPL layer with HTM as element on the transparent cathode layer to obtain an evaporated film thickness ofThe OLED element of the present invention was obtained.
The structure of the compound used in example 3 above is as follows:
example 4
An organic electroluminescent device 200 having a structure as shown in fig. 2, comprising a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first luminescent layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second luminescent layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213, was prepared by the similar preparation method as described in example 3.
Comparative example 1
By following the same procedure as in example 3 except substituting E01 for the compound represented by the formula (I) of the present invention in step 5), comparative element 1 was obtained;
The driving voltage and current efficiency of the organic electroluminescent elements prepared in example 3, example 4 and comparative example 1 and the lifetime of the elements were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the voltage was boosted at a rate of 0.1V per second,measurement of the luminance of the organic electroluminescent device reaching 1000cd/m 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
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Wherein Me is methyl; ph is phenyl; phPh is biphenyl; ad is 2, 2-adamantyl; FR is 9, 9-fluorenyl.
As can be seen from table 1, the compound of the present invention provides an organic electroluminescent element having high efficiency and long life as a material for a light-emitting layer, the element has a low driving voltage and improved current efficiency, and the LT90% lifetime is excellent, indicating that the compound of the present invention is an organic electroluminescent material having excellent performance.
The compound E01 of comparative example 1 is different from the compound of the present invention in that after the phenanthrooxazole of E01 is introduced into the triarylamine group, the electron transport ability is weaker than the hole transport ability, resulting in imbalance in transfer of excitons in the element, an increase in element driving voltage, and a decrease in efficiency. The compound of the invention improves the electron transmission capability after imidazole or pyrazine groups are introduced into dibenzofuran, dibenzothiophene or carbazole, so that the compound has larger improvement on the exciton transmission performance when being used as a main material with n-type RH01, the exciton transmission in the element is more balanced, and the element performance is obviously 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):
wherein two adjacent W 1 And W is 2 A group of formula (II) or formula (III); two adjacent X' s 1 And X 2 A group of formula (IV);
g is selected from O, S, CR 3 R 4 、SiR 3 R 4 Or NAr 5 The method comprises the steps of carrying out a first treatment on the surface of the Two adjacent "≡" groups of formula (II) and formula (III) indicate two adjacent groups W of formula (I) 1 And W is 2 Two adjacent "≡" indications of formula (IV)(I) Two adjacent groups X in (a) 1 And X 2 ；
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 Are identical to or different from each other and are each independently selected from hydrogen, deuterium, cyano, halogen atoms, 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 Aryl silyl group, any adjacent two or more R 1 、R 2 Optionally bonded 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;
L 1 selected from single bonds, 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 、Ar 3 、Ar 4 、Ar 5 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.
2. The amino compound of claim 1, wherein the amino compound is selected from the group consisting of:
wherein R is 1 、R 5 、R 6 、G、L 1 、Ar 1 、Ar 2 、Ar 3 、Ar 4 And m has the same meaning as in claim 1.
3. An amino compound according to claim 1 or 2, characterized in that G is selected from O, S or NAr 5 The method comprises the steps of carrying out a first treatment on the surface of the m is 0, 1 or 2; r is R 1 ～R 6 Each independently selected from the group consisting of hydrogen, deuterium, nitrile, 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 anthracyl, substituted or unsubstituted benzanthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted 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, a substituted or unsubstituted dibenzothiophenyl group;
Ar 1 ～Ar 5 each independently selected from the group consisting of: phenyl, naphthyl, anthryl, benzanthraceyl, phenanthryl, pyrenyl,A group, perylene group, fluoranthenyl group, naphthacene group, pentacene group, benzopyrene group, biphenyl group, terphenyl group, tripolyphenyl group, tetrabiphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthrene group, triphenylene group, dihydropyrenyl group, tetrahydropyrenyl group, cis-or trans-indenofluorenyl group, cis-or trans-indenocarbazolyl group, indolocarbazolyl group, benzofuranocarbazolyl group, benzothiophenocarbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, 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, anthracnose oxazolyl, 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-diazapyrenyl, 4,5,9, 10-tetraazaperylene group, pyrazinyl group, phenazinyl group, phenoxazinyl group, phenothiazinyl group, fluorocyclyl group, naphthyridinyl group, azacarbazolyl group, benzocarboline group, carboline group, phenanthroline group, 1,2, 3-triazolyl group, 1,2, 4-triazolyl group, benzotriazole group, 1,2, 3-oxadiazolyl group, 1,2, 4-oxadiazolyl group, 1,2, 5-oxadiazolyl group, 1,3, 4-oxadiazolyl group, 1,2, 3-thiadiazolyl group, 1,2, 4-thiadiazolyl group, 1,2, 5-thiadiazolyl group, 1,3, 5-triazinyl group, 1,2, 4-triazinyl group, 1,2, 3-triazinyl group, tetrazolyl group, 1,2,4, 5-tetrazinyl group, 1,2,3, 4-tetrazolyl group, 1,2, 3-tetrazolyl group, 3, 5-tetrazolyl group, quinolizinyl group, quinolizine group, pterine group, indolizinyl group, or pterine group A group that is a combination of these systems.
4. The amino compound of claim 1, wherein R 1 ～R 6 Each independently selected from the group consisting of hydrogen, deuterium, t-butyl, substituted or unsubstituted phenyl; ar (Ar) 1 ～Ar 5 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 pyrenylA 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.
5. The amino compound of claim 1, wherein L is 1 Selected from a single bond or a group consisting of groups III-1 to III-24:
wherein T is 3 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 to 5, wherein said amino compound is selected from the group consisting of structures shown in C01 to C210:
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wherein each x— is independently selected from one of the following structures:
* -and- (x) represents a bond.
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 each organic layer may be one, two or more layers; the hole transport layer or/and the light-emitting layer contains the amino compound according to any one of claims 1 to 6.
10. A consumer product comprising the organic electroluminescent device of any one of claims 8-9.
CN202310526311.0A 2023-05-11 2023-05-11 Amino compound, organic electroluminescent element and organic electroluminescent device Pending CN116535419A (en)

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