An amino compound, an organic electroluminescent element, and an organic electroluminescent device.

Abstract

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

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescence technology, specifically relating to an amino compound and its application in organic electroluminescent elements and devices. Background Technology

[0002] The materials used in organic light-emitting diodes (OLEDs) are mostly pure organic compounds or organometallic complexes formed by organic compounds and metals. Depending on their application, they can be categorized as hole injectors, hole transporters, luminescent materials, electron transporters, and electron injectors. Here, organic compounds with relatively low ionization energies are primarily used as hole injectors or hole transporters, while organic compounds with high electronegativity are primarily used as electron injectors or electron transporters. Furthermore, the material used as the light-emitting auxiliary layer preferably meets the following characteristics.

[0003] First, the materials used in organic light-emitting diodes (OLEDs) need good thermal stability because Joule heating occurs inside the OLED due to charge migration. Currently, the materials commonly used as hole transport layers have low glass transition temperatures, leading to crystallization and reduced luminous efficiency at low temperatures. Second, to reduce the driving voltage, the organic materials adjacent to the cathode and anode need to be designed with low charge injection barriers and high charge mobility. Third, energy barriers inevitably exist at the interfaces between the electrodes and organic layers, and between organic layers, resulting in the accumulation of some charge. Therefore, materials with excellent electrochemical stability are required.

[0004] Organic electroluminescent devices generally consist of an anode, a hole injection layer, a hole transport layer, an electroluminescent layer (serving as an energy conversion layer), an electron transport layer, and a cathode, stacked sequentially. When a voltage is applied to the anode and cathode, an electric field is generated between the electrodes. Under the influence of this electric field, electrons on the cathode side move towards the electroluminescent layer, and holes on the anode side also move towards the electroluminescent layer. Electrons and holes combine in the electroluminescent layer to form excitons. These excitons are in an excited state and release energy, thereby causing the electroluminescent layer to emit light.

[0005] In existing technologies, materials that can be used to fabricate hole transport layers in organic electroluminescent devices are disclosed in KR1020180113731, CN201710407382.3, CN201610183587.3, CN201380045022.3, CN201180044705.8, and CN201910765403.8. However, it remains necessary to continue developing novel materials to further improve the performance of electronic components. Summary of the Invention

[0006] The purpose of this disclosure is to provide an amino compound, an organic electroluminescent material, a light-emitting element, and a light-emitting device for improving the performance of organic electroluminescent elements.

[0007] To achieve the above objectives, the present invention adopts the following technical solution:

[0008] An amino compound having the general structural formula shown in formula (I):

[0009]

[0010] Among them, two adjacent W 1 and W 2 The group representing formula (II) or formula (III); two adjacent X groups 1 and X 2 The group representing formula (IV);

[0011]

[0012] G is selected from O, S, CR 3 R 4 SiR 3 R 4 or NAr 5 The two adjacent “^^” symbols in formulas (II) and (III) indicate the two adjacent groups W in formula (I). 1 and W 2 In formula (IV), two adjacent "^" symbols indicate two adjacent groups X in formula (I). 1 and X 2 ;

[0013] R 1 R 2 R 3 R 4 R 5 R 6 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, cyano, halogen atoms, and substituted or unsubstituted C1-C atoms. 30 Alkyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C3-C 30 Cycloalkyl, substituted or unsubstituted C2-C 50 heteroaryl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 50 aryloxy groups, substituted or unsubstituted C1-C 30 Alkyl thio, substituted or unsubstituted C5-C 50 aryl thio, substituted or unsubstituted C1-C 30Alkylamine, substituted or unsubstituted C5-C 50 Arylamine, substituted or unsubstituted C1-C 30 Alkyl silyl, substituted or unsubstituted C5-C 50 A group consisting of arylsilyl groups, any two or more adjacent R 1 R 2 They can be arbitrarily joined or fused to form substituted or unsubstituted rings, which may or may not contain heteroatoms N, O, S, P, B, Si or Se.

[0014] L 1 Choose C6 to C6, whether they are free single bonds, substituted, or unsubstituted. 50 aryl, substituted or unsubstituted C2-C 50 Groups composed of heteroaryl groups;

[0015] m is selected from integers from 0 to 5;

[0016] Ar 1 Ar 2 Ar 3 Ar 4 Ar 5 Each independently selects either substituted or unsubstituted C6-C6. 50 Aryl, substituted or unsubstituted C5-C 50 Arylamine, substituted or unsubstituted C6-C 50 Floated aryl, substituted or unsubstituted C2-C 50 A group composed of heteroaryl groups.

[0017] The alkyl group used in this invention refers to a monovalent functional group obtained by removing a hydrogen atom from a straight-chain or branched saturated hydrocarbon with 1 to 40 carbon atoms. Non-limiting examples include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, etc.

[0018] In this invention, aryl groups contain 6 to 60 carbon atoms, and heteroaryl groups contain 2 to 60 carbon atoms and at least one heteroatom, provided that the total number of carbon atoms and heteroatom is at least 5; the heteroatom is preferably selected from N, O, or S. In this case, the two or more rings of the heteroaryl group can be simply attached to each other or attached in a condensed form, and further, it may also include a form condensed with the aryl group. As non-limiting examples of aryl and heteroaryl groups, particularly those selected from the following groups: phenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, pyrene, ... alkyl, peryl, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, azophenyl, terphenyl, trimerphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthrene, triphenylene, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorenyl, cis or trans indo[a]carbazoyl, indole[a]carbazoyl, benzo[a]furan[a]carbazoyl, benzo[a]thio[a]carbazoyl, benzo[a]carbazoyl, dibenzo[a]carbazoyl, azadibenzo[g,Id]naphtho[2,1,8-cde]azine, trimerinyl, isotrimerinyl, spirotrimerinyl, spiroisotrimerinyl, furanyl, benzo[a]furanyl, isobenzo[a]furanyl Dibenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, pyrroleyl, indoleyl, isoindoleyl, carbazoyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo[5,6]quinolinyl, benzo[6,7]quinolinyl, benzo[7,8]quinolinyl, phenothiazinyl, phenotoxazinyl, pyrazolyl, indazoleyl, imidazoleyl, benzimidazoleyl, naphthimazoleyl, phenanthimazoleyl, pyridiniumimazoleyl, pyraziniumimazoleyl, quinoxoliniumimazoleyl, oxazolyl, benzoxoxazolyl, naphthoxazolyl, anthraquinonexazolyl, phenanthoxazolyl, isoxazolyl, 1,2- Thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazabenzophenanthryl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthrayl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenoxazinyl, phenthiazinyl, fluoresceinyl, naphridinyl, azacarbazolyl, benzocarbaolinyl, carbaolinyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1 The group consisting of or derived from the group consisting of 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-tetraazinyl, 1,2,3,4-tetraazinyl, 1,2,3,5-tetraazinyl, purine, pteridine, indazinyl, quinazolinyl, and benzothiadiazolyl.

[0019] The term "halogen" or "halogen atom" used in this invention refers to a substance selected from fluorine, chlorine, bromine, or iodine.

[0020] Furthermore, the amino compound is selected from the group consisting of the following structures:

[0021]

[0022] The symbols used are the same as those defined above.

[0023] Furthermore, G is selected from O, S, or NAr. 5 Furthermore, m is 0, 1, or 2.

[0024] Furthermore, the R 1 ~R 6 Each is independently selected from hydrogen, deuterium, nitrile, methyl, ethyl, isopropyl, isobutyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted anthraquinone, substituted or unsubstituted benzo[a]anthraquinone, substituted or unsubstituted pyrene, substituted or unsubstituted... The group consisting of alkyl, substituted or unsubstituted perylyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl.

[0025] Furthermore, the Ar 1 ~Ar 5 Each is independently selected from the group consisting of the following groups: phenyl, naphthyl, anthracene, benzo[a]anthracene, phenanthryl, pyrene, alkyl, perylene, fluoranyl, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, azophenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirodifluorenyl, dihydrophenanthrene, triphenylene, dihydropyrene, tetrahydropyrene, cis or trans indo[a]fluorenyl, cis or trans indo[a]carbazoyl, indole[a]carbazoyl, benzo[a]furan[a]carbazoyl, benzo[a]thio[a]carbazoyl, benzo[a]carbazoyl, dibenzo[a]carbazoyl, azadibenzo[g,Id]naphtho[2,1,8-cde]azine, trimerinyl, isotrimerinyl, spirotrimerinyl, spiroisotrimerinyl, furanyl, benzo[a]furanyl, isobenzo[a]furanyl Dibenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, pyrroleyl, indolyl, isoindolyl, carbazoyl, pyridyl, quinolinyl, isoquinolinyl, acridineyl, phenanthridineyl, benzo[5,6]quinolinyl, benzo[6,7]quinolinyl, benzo[7,8]quinolinyl, phenothiazinyl, phenotoxazinyl, pyrazolyl, indazoleyl, imidazoyl, benzimidazole, naphthiazole, phenanthiazole, pyridiniumimidazoyl, pyraziniumimidazoyl, quinoxoliniumimidazoyl, oxazolyl, benzoxoxazolyl, naphthiazole, anthraquinonexazolyl, phenanthiazole, isoxazolyl, 1, 2-Thiazolyl, 1,3-Thiazolyl, benzothiazolyl, pyridazinyl, hexaazabenzophenanthryl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthrayl, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenoxazinyl, phenthiazinyl, fluoresceinyl, naphridinyl, azacarbazolyl, benzocarbaolinyl, carbaolinyl, phenanthrolinel, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazole The group consisting of 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-tetraazinyl, 1,2,3,4-tetraazinyl, 1,2,3,5-tetraazinyl, purine, pteridine, indazinyl, quinazolinyl, benzothiadiazolyl, or a combination thereof.

[0026] According to an embodiment of the present invention, the R 1 ~R 6 Each is independently selected from the group consisting of hydrogen, deuterium, tert-butyl, substituted or unsubstituted phenyl groups.

[0027] According to an embodiment of the present invention, the Ar 1 ~Ar 5Each of the following is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthraquinone, substituted or unsubstituted benzo[a]anthraquinone, substituted or unsubstituted pyrene, substituted or unsubstituted [a] The group consisting of alkyl, substituted or unsubstituted perylyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0028] In this invention, a heteroalkyl group refers to an alkyl group in which a hydrogen atom or -CH2- is substituted by at least one heteroatom, wherein the heteroatom is selected from halogens, nitrile groups, N, O, S, or silicon. Non-limiting examples include difluoromethyl, trifluoromethyl, trifluoroethyl, pentafluoroethyl, nitrile, acetonitrile, methoxymethyl, methoxyethyl, trimethylsilyl, triisopropylsilyl, etc. A haloalkyl group refers to an alkyl group in which a hydrogen atom is partially or completely substituted by a halogen. Non-limiting examples include fluorotoluene, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoroethyl, pentafluoroethyl, etc.

[0029] The alkenyl or ynyl group used in this invention contains at least two carbon atoms. As a non-limiting example, the alkenyl or ynyl group is preferably considered to refer to the following groups: cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentyynyl, hexynyl, heptenyl, or octyynyl.

[0030] The alkoxy or alkylthio groups used in this invention are preferably alkoxy or alkylthio groups having 1 to 40 carbon atoms, and are considered to be methyl methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptoxy, cycloheptoxy, n-octoxy, cyclooctoxy, 2-ethylhexyloxy, pentafluoroethoxy, and 2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio 2,2,2-trifluoroethylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethyleneoxy, ethylenethio, propyleneoxy, propylenethio, butenthio, butenoxy, penenoxy, penenthio, cyclopentenoxy, cyclopententhio, hexenoxy, hexenthio, cyclohexenoxy, acetylenoxy, acetylenthio, propylenoxy, propylenthio, butylenoxy, butylenthio, penylenoxy, penylenthio, hexylenoxy, hexylenthio.

[0031] Generally, the cycloalkyl and cycloalkenyl groups according to the present invention can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, or cycloheptenyl, wherein one or more -CH2- groups can be replaced by N, O, or S to form heterocyclic alkyl or heterocyclic alkenyl groups. For example, one -CH2- group in cyclopentyl is replaced by O to form tetrahydrofuranyl, and one -CH2- group in cyclohexyl is replaced by O to form tetrahydropyranyl, etc. In addition, one or more hydrogen atoms can be replaced by deuterium atoms, halogen atoms, or nitrile groups.

[0032] The aryl group used in this invention refers to R'O - The monovalent functional group represented by R' is an aryl group with 6 to 60 carbon atoms. Non-limiting examples of such aryl groups include phenoxy, naphthoxy, and biphenoxy groups.

[0033] The aryl thio group used in this invention refers to R”S - The monovalent functional group represented by "R" is an aryl group with 6 to 60 carbon atoms. Non-limiting examples of such arylthio groups include phenylthio, naphthio, and biphenylthio.

[0034] The alkylsilyl group used in this invention refers to a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, wherein the number of carbon atoms constituting the alkylsilyl group is at least 3. Non-limiting examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, etc. The arylsilyl group refers to a silyl group substituted with at least one aryl group having 6 to 60 carbon atoms. Non-limiting examples include phenyldimethylsilyl, naphthyldimethylsilyl, phenyldiethylsilyl, diphenylmethylsilyl, diphenylethylsilyl, triphenylsilyl, etc.

[0035] The alkylamine group used in this invention refers to an amino group that is substituted with an alkyl group having 1 to 40 carbon atoms, or an amino group that is substituted with two alkyl groups having 1 to 40 carbon atoms. Non-limiting examples of alkylamine groups include methylamine, dimethylamine, ethylamine, diethylamine, etc.

[0036] The arylamine group used in this invention refers to an amino group substituted with an aryl group having 6 to 60 carbon atoms, or an amino group substituted with two aryl groups having 6 to 60 carbon atoms. Non-limiting examples of arylamine groups include aniline, diphenylamine, 1-naphthylamine, 2-naphthylamine, N-phenylnaphth-1-amine, carbazole, phenoxazine, etc.

[0037] In the context of this invention, "alkyl carbonyl", "alkoxy carbonyl", "aryl carbonyl", "arylboron carbonyl", and "alkylboron carbonyl" refer to the substituted carbonyl group (-COR*), wherein R* is preferably selected from the group consisting of alkyl, alkoxy, cycloalkyl, aryl, heteroaryl, arylboron, and alkylboron.

[0038] The arylphospho group used in this invention refers to a diarylphospho group substituted with an aryl group having 6 to 60 carbon atoms. Non-limiting examples of arylphospho groups include diphenylphospho and di(4-trimethylsilylphenyl)phospho. Aryloxophospho is formed when the phosphorus atom of a diarylphospho group is oxidized to its highest valence state.

[0039] The arylboryl group used in this invention refers to a diarylboryl group substituted with an aryl group having 6 to 60 carbon atoms. Non-limiting examples of arylboryl groups include diphenylboryl and di(2,4,6-trimethylphenyl)boryl. Alkylboryl groups refer to dialkylboryl groups substituted with an alkyl group having 1 to 40 carbon atoms. Non-limiting examples of alkylboryl groups include di-tert-butylboryl and diisobutylboryl.

[0040] According to the present invention, an arylalkyl group refers to an alkyl group in which at least one hydrogen atom of a straight-chain or branched saturated hydrocarbon having 1 to 40 carbon atoms is replaced by an aryl group having 6 to 60 carbon atoms. As a non-limiting example, it can be phenylmethyl, diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, etc.

[0041] According to the present invention, an alkylaryl group refers to an aryl group having at least one hydrogen atom substituted by a straight-chain or branched saturated hydrocarbon having 1 to 40 carbon atoms. As a non-limiting example, it can be methylphenyl, dimethylphenyl, trimethylphenyl, tert-butylphenyl, isopropylphenyl, etc.

[0042] The substituents of the substituted alkyl, substituted aryl, substituted heteroaryl, substituted arylamine, substituted fused aryl, substituted arylene, and substituted heteroarylene groups described in this invention are each independently selected from at least one of the following groups: deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, C1-C 40 Alkyl, C1-C 40 Haloalkyl, C2-C 40 alkenyl, C2-C 40 alkynyl group, C1-C 40 Alkoxy, C1-C 40 Alkylthio, C3-C 40 cycloalkyl, C3-C 40 Cycloalkenyl, 3- to 7-membered heterocyclic alkyl, C6-C 60 Aryloxy group, C6-C 60 Aryl thiols, unsubstituted or with one or more C6-C groups 60 Aryl-substituted 3- to 30-membered heteroaryl groups, unsubstituted or deuterated groups, one or more C1-C groups. 40 At least one substituted C6-C group of alkyl and one or more 3- to 30-membered heteroaryl groups 60 Aryl, tri(C1-C 40) alkylsilyl, tri(C6-C 60 )Arylsilyl, di(C1-C 40 ) alkyl (C6-C 60 Arylsilyl, C1-C 40 Alkyl di(C6-C) 60 Arylsilyl, C1-C 40 Alkyl carbonyl, C1-C 40 alkoxycarbonyl, C6-C 60 aryl carbonyl, di(C6-C) 60 ) arylboron carbonyl, di(C1-C 40 )alkylboron carbonyl, C1-C 40 Alkyl (C6-C) 60 )Arylboronic carbonyl, C6-C 60 Aryl (C1-C 40 )alkyl, and C1-C 40 Alkyl (C6-C) 60 Aryl.

[0043] In this invention, arylene refers to a divalent functional group obtained by removing two hydrogen atoms from an aromatic hydrocarbon with 6 to 60 carbon atoms. Non-limiting examples include phenylene, naphthylene, phenanthrylene, anthraceneylene, fluoreneylene, and spirodifluoreneylene.

[0044] In this invention, heteroaryl or hetero-aryl refers to a divalent functional group obtained by removing two hydrogen atoms from a heteroaromatic hydrocarbon with 2 to 60 carbon atoms. Non-limiting examples include pyridyl, quinoline, isoquinoline, carbamoline, pyrimidinyl, and triazineyl.

[0045] Based on the aforementioned arylene and heteroarylene groups as divalent functional groups, and N and Ar 3 Ar 4 Connection, preferably, the L 1 Selected from single bonds or groups consisting of the following groups from III-1 to III-24:

[0046]

[0047] Among them, T 3 Selected from O, S, Se, CR'R”, SiR ’ R” or NAr';

[0048] Z 11 Z 12 Z 13 Z 14 Each is independently selected from hydrogen, deuterium, halogen atom, hydroxyl group, nitrile group, nitro group, amino group, amidine group, hydrazine group, hydrazone group, carboxyl group or its carboxylate, sulfonic acid group or its sulfonate, phosphate group or its phosphate, C1-C60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy groups, C3-C 60 Cycloalkane group, C3-C 60 Cycloolefinic, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 aryl sulfide group, or substituted or unsubstituted C2-C 60 Groups composed of heteroaryl groups;

[0049] y1 represents an integer from 1 to 4; y2 represents an integer from 1 to 6; y3 represents an integer from 1 to 3; y4 represents an integer from 1 to 5; y5 represents an integer of 1 or 2.

[0050] R' and R” are each independently selected from C1-C 60 Alkyl, C1-C 60 heteroalkyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 Aromatic amino group, or substituted or unsubstituted C2-C 60 Groups composed of heteroaryl groups, R ’ R' and R'" may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, the formed rings containing or not containing one or more heteroatoms N, P, B, O or S; preferably, R' and R'" are methyl, phenyl or fluorenyl.

[0051] Ar' chooses freely from C1 to C. 60 Alkyl, C1-C 60 heteroalkyl, C3-C 60 cycloalkyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 Fused aryl, substituted or unsubstituted C6-C 60 Aromatic amino group, or substituted or unsubstituted C2-C 60 The group consisting of heterocyclic aryl groups; preferably, Ar' is methyl, ethyl, phenyl, biphenyl, or naphthyl;

[0052] In this context, the dashed lines represent the bonding sites of functional groups.

[0053] Preferably, the L 1 Selected from single bonds or groups consisting of the following groups: III-1 to III-15, III-24

[0054]

[0055] Preferably, the Z 11 Z 12 Z 13 Z 14 Each group is independently selected from groups composed of hydrogen, deuterium, fluorine, and nitrile groups.

[0056] Furthermore, the amino compound is selected from one or more of the following C01 to C210 structures:

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066] Wherein, *—X—* is independently selected from *—O—*, *—S—*, or one of the structures shown below:

[0067]

[0068] *— and —* represent connector keys.

[0069] As used herein, “combination” or “group” means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that can be conceived by one of ordinary skill in the art from the applicable list. For example, alkyl and deuterium atoms can be combined to form partially or fully deuterated alkyl groups; halogens and alkyl groups can be combined to form haloalkyl substituents, such as trifluoromethyl; and halogens, alkyl groups, and aryl groups can be combined to form haloaralkyl groups.

[0070] An organic electroluminescent material, wherein the organic electroluminescent material comprises the amino compound described above; the organic electroluminescent material comprising the amino compound of the present invention has the ability to transport charge carriers.

[0071] Organic electroluminescent materials can be composed solely of the amino compounds of this invention, or they can contain other compounds simultaneously.

[0072] 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) material, or an electron blocking layer material.

[0073] This invention also provides the application of the above-described amino compounds in the preparation of organic electroluminescent elements.

[0074] The present invention also provides an organic electroluminescent element, comprising: a first electrode, a second electrode, a CPL layer, and one or more organic layers disposed between the first electrode and the second electrode; at least one of the organic layers and the CPL layer comprises the amino compound described above.

[0075] The organic electroluminescent element comprises a cathode, an anode, a CPL (Chemical Polarizing Layer), and at least one emitting layer. In addition to these layers, it may also comprise other layers, such as, 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 generation layers. An intermediate layer having, for example, exciton blocking functionality may also be introduced between two emitting layers. However, it should be noted that each of these layers is not necessarily required. The organic electroluminescent element described herein may comprise one emitting layer, or it may comprise multiple emitting layers. That is, various luminescent compounds capable of emitting light are used in the emitting layers. A system having three emitting layers is particularly preferred, wherein the three layers can exhibit blue, green, and red light emission. If more than one emitting layer is present, according to the invention, at least one of these layers comprises a compound of the invention.

[0076] Furthermore, the organic electroluminescent element according to the present invention does not contain a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer, that is, the light-emitting layer is directly adjacent to the hole injection layer or the anode, and / or the light-emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode.

[0077] In the other layers of the organic electroluminescent element according to the invention, particularly in the hole transport layer and the light-emitting layer, as well as in the CPL, all materials can be used in accordance with the manner commonly used in the prior art. Those skilled in the art will therefore be able to combine all materials known about organic electroluminescent elements in the light-emitting layer according to the invention without inventive effort.

[0078] Regarding the organic electroluminescent element of the present invention, except that one or more of the above-described organic layers contain the amino compounds described above, the organic layers and electrodes can be formed using materials and methods known in the art.

[0079] Furthermore, the material that can be used as the anode in the organic electroluminescent element according to the present invention is not particularly limited. As a non-limiting example, metals such as vanadium, chromium, copper, zinc, gold, and aluminum, or alloys thereof, can be used; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylidene-1,2-dioxothiophene] (PEDT), polypyrrole, and polyaniline; and carbon black, etc.

[0080] The material that can be used as the cathode in the organic electroluminescent element according to the present invention is not particularly limited. As a non-limiting example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or their alloys can be used; as well as multilayer structure materials such as LiF / Al or Li2O / Al.

[0081] The material that can be used as the substrate in the organic electroluminescent element according to the present invention is not particularly limited. As a non-limiting example, silicon wafers, quartz, glass plates, metal plates, or plastic films and sheets can be used.

[0082] Furthermore, the following organic electroluminescent elements are preferred, which can be applied with one or more layers by means of a sublimation method, wherein in a vacuum sublimation apparatus at temperatures below 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 be even lower, for example, below 10 Pa. -7 Pa.

[0083] The organic electroluminescent element, preferably as described below, can also be applied by means of organic vapor deposition or by means of carrier gas sublimation, wherein, in 10 -5 The material is applied at a pressure between Pa and 1 Pa. A particular example of this method is the organic vapor jet printing method, in which the material is applied directly through a nozzle and is therefore structured.

[0084] Furthermore, the following organic electroluminescent elements are preferred, which produce one or more layers from solution, for example by spin coating, or by any desired printing method such as screen printing, flexographic printing, offset printing, photoinitiated thermal imaging, thermal transfer, inkjet printing, or nozzle printing. Soluble compounds, for example, are obtained by means of compounds represented by suitable substitution formula (I). These methods are also particularly suitable for oligomers, dendritic macromolecules, and polymers. Additionally, mixing methods are feasible, in which one or more layers are applied from solution and one or more additional layers are applied by vapor deposition.

[0085] These methods are generally known to those skilled in the art, and they can be applied to organic electroluminescent elements containing compounds according to the invention without any inventive effort.

[0086] Therefore, the present invention 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 by means of an organic vapor deposition method or by means of carrier gas sublimation, and / or by means of spin coating or printing method from a solution to apply at least one layer.

[0087] Furthermore, the present invention relates to compounds comprising at least one of the compounds of the present invention as described above. The same preferred embodiments as noted above regarding organic electroluminescent elements apply to the compounds of the present invention. In particular, the compounds may also preferably contain other compounds. Processing the compounds of the present invention from the liquid phase, for example by spin coating or printing methods, requires formulations for processing the compounds of the present invention, which may be, for example, solutions, dispersions, or emulsions. For this purpose, mixtures of two or more solvents may preferably be used. Suitable and preferred solvents include, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, naphthalene, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, (-)-fenone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methyl anisole, 4-methyl anisole, 3,4-dimethyl anisole, 3,5-dimethyl anisole, acetophenone, α-terpenes. The solvents are benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decahydronaphthalene, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-methylisopropylbenzene, phenethyl ether, 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, pentabenzene, hexene, heptene, octene, 1,1-bis(3,4-dimethylphenyl)ethane, or mixtures of these solvents.

[0088] 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.

[0089] Furthermore, the hole transport layer, light-emitting layer, or CPL layer comprises the amino compound of the present invention.

[0090] A consumer product made from the aforementioned organic electroluminescent device includes the organic electroluminescent device provided by the present invention.

[0091] The consumer products described in this invention can be one of the following: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for internal or external lighting and / or signaling, head-up displays, fully transparent or partially transparent displays, flexible displays, laser printers, telephones, cellular phones, tablet computers, tablet phones, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, microdisplays with a diagonal of less than 2 inches, 3D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple displays tiled together, theater or stadium screens, phototherapy devices, and signs.

[0092] In addition, unless otherwise specified, all raw materials used in this invention can be obtained commercially available. Any range described in this invention includes the end value and any value between the end values, as well as any subrange formed by the end value or any value between the end values.

[0093] The present invention also relates to mixtures comprising at least one compound of formula (I) or the preferred embodiments described above and at least one other compound. If the compound according to the invention is used as a matrix material, the other compounds may be fluorescent or phosphorescent emitters. Thus, the mixture may further comprise other materials as additional matrix materials. The present invention also relates to the use of the compounds of the invention in electronic devices. Preferably, as mentioned in the context, the compounds according to the invention are used in hole transport layers or as matrix materials in light-emitting layers. The compounds according to the invention and the electronic devices, particularly organic electroluminescent devices, obtained therefrom differ from the prior art in one or more of the following surprising advantages:

[0094] The amino compounds described in this invention have novel rigid structures such as large planar conjugated imidazobenzofuran, imidazobenzothiophene, pyrazinbenzofuran, or pyrazinbenzothiophene. As for the compounds represented by the general formula (I) of this invention, they are suitable as constituent materials of the light-emitting layer of the organic electroluminescent element of this invention because they have the following characteristics: (1) high carrier mobility; (2) high internal quantum efficiency; (3) stable thin film state; and (4) excellent heat resistance.

[0095] Regarding the organic electroluminescent element of the present invention, which uses the amino compound represented by the above general formula (I) of the present invention as the main material of the light-emitting layer, since a compound with a 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 with high efficiency, low driving voltage, and long lifetime.

[0096] Furthermore, in this invention, by forming the light-emitting layer using an amino compound of the above general formula (I), the high quantum efficiency and heat resistance of the compound can be utilized to the maximum extent, enabling the realization of a long-life organic electroluminescent element with higher efficiency.

[0097] Furthermore, in the organic electroluminescent element of the present invention, in which an amino compound represented by the above general formula (I) is used as a constituent material in at least one layer of the above-mentioned light-emitting layer or a laminated film with two or more light-emitting layers, a high-efficiency, low-drive-voltage, and long-life organic electroluminescent element can be realized because a compound with high carrier mobility, high internal quantum efficiency, excellent amorphousness, and stable film state is used.

[0098] The advantages mentioned above are not accompanied by a weakening of other electronic properties.

[0099] It should be noted that variations of the embodiments described in this invention fall within the scope of this invention. Each feature disclosed in this invention may be replaced by an alternative feature having the same, equivalent, or similar purpose unless explicitly excluded. Therefore, unless otherwise stated, each feature disclosed in this invention should be considered an instance of a class series or an equivalent or similar feature.

[0100] All features of this invention can be combined with each other in any way, unless particular features and / or steps are mutually exclusive. This applies particularly to the preferred features of the invention. Similarly, features that are not necessarily combined can be used alone (and not in combination). Furthermore, it should be noted that many features, especially those of the preferred embodiments of the invention, are inventive in themselves and should not be considered merely as part of the embodiments of the invention. For these features, independent protection may be sought in addition to or as an alternative to each of the currently claimed inventions.

[0101] The teachings on the technical actions disclosed in this invention can be extracted and combined with other embodiments. The invention is explained in more detail through the following embodiments, but is not intended to limit the invention thereto. Based on the description, those skilled in the art will be able to practice the invention within the entire scope disclosed and prepare other compounds of the invention and use them in electronic components, or use the methods of the invention, without inventive effort. Attached Figure Description

[0102] To more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the drawings used in the description of the embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0103] Figure 1 A schematic diagram of an organic light-emitting device 100 is shown. The diagram is not necessarily drawn to scale. 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. Device 100 can be fabricated by sequentially depositing the described layers.

[0104] Figure 2 A schematic diagram of an organic light-emitting device 200 with two light-emitting layers is shown. The device 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. The device 200 can be fabricated by sequentially depositing the described layers. Because most common OLED devices have one light-emitting layer, and device 200 has a first light-emitting layer and a second light-emitting layer, the emission peaks of the first and second light-emitting layers can be overlapping, cross-overlapping, or non-overlapping. Materials similar to those described with respect to device 100 can be used in the corresponding layers of device 200. Figure 2 Provides an example of how to add layers from the structure of device 100. Detailed Implementation

[0105] To make the objectives, technical solutions, and advantages of this invention clearer, the technical solutions of this invention will be described in detail below. Obviously, the described embodiments are merely some embodiments of this invention, and not all embodiments. Based on the embodiments of this invention, all other implementation methods obtained by those skilled in the art without creative effort are within the scope of protection of this invention.

[0106] In this invention, the preparation methods are all conventional unless otherwise specified. All raw materials used are available from publicly available commercial sources unless otherwise specified, and all percentages are by mass unless otherwise specified. This invention provides a series of novel organic compounds, all reactions of which are carried out under well-known suitable conditions. Some involve simple organic preparations, such as the preparation of phenylboronic acid derivatives, which can be synthesized with skilled operation and are not described in detail in this invention.

[0107] Any range described in this invention includes the endpoint, any value between the endpoints, and any subrange consisting of the endpoint or any value between the endpoints.

[0108] The following embodiments use the following testing instruments and methods for performance testing of OLED materials and components:

[0109] OLED component performance testing conditions:

[0110] Luminosity and chromaticity coordinates: tested using a PhotoResearch PR-715 spectral scanner;

[0111] Current density and turn-on voltage: tested using a Keithley 2420 digital source meter;

[0112] Power efficiency: Tested using NEWPORT 1931-C;

[0113] Life test: The LTS-1004AC life test device was used.

[0114] Example 1

[0115] The preparation method of compound C19 includes the following steps:

[0116] Step 1: Preparation of compound Int.-1

[0117]

[0118] Under nitrogen protection, 37.8 mmol of trimethylsilylacetylene was dissolved in 50 mL of triethylamine, and 45.5 mmol of 3-bromo-2-cyanobenzothiophene, 4.0 mmol of cuprous iodide, 4.0 mmol of palladium acetate and 8.0 mmol of DPEPos (bis(2-diphenylphosphine) ether) were added. The mixture was heated to reflux and stirred for 6 hours, concentrated under reduced pressure and dried, and purified by silica gel column chromatography to give intermediate Int.-1 in 84% yield.

[0119] Step 2: Preparation of compound Int.-2

[0120]

[0121] Under nitrogen protection, 20.0 mmol of the previously prepared Int.-1, 40.0 mmol of nitromethane, 40.0 mmol of potassium hydroxide, and 50 mL of DMSO were mixed, heated to 110 °C, and stirred for 45 minutes. After cooling to room temperature, the reaction solution was poured into 150 mL of ice water, filtered, the filter cake was washed with water, and recrystallized from methanol to give compound Int.-2, a yellow solid, with a yield of 92%.

[0122] Step 3: Preparation of compound Int.-3

[0123]

[0124] 20.0 mmol of the previously prepared Int.-2, 40.0 mmol of triethylamine, and 80 mL of dichloromethane were mixed and cooled to 0 °C. 24.0 mmol of benzoyl chloride was added dropwise, and the mixture was stirred for 30 minutes. The mixture was then heated to room temperature and stirred for 2 hours. 50 mL of water was added, the organic phase was separated, washed with water, dried, filtered, and the filtrate was concentrated and dried under reduced pressure to obtain compound Int.-3, a yellow solid, with a yield of 100%.

[0125] Step 4: Preparation of compound Int.-4

[0126]

[0127] 20.0 mmol of the previously prepared Int.-3, 100 mL of methanol and 50 mL of water were mixed, and then 0.1 mol of ammonium chloride and 0.1 mol of iron powder were added. The mixture was stirred at room temperature for 15 hours, filtered, and the filtrate was concentrated to dryness under reduced pressure. The residue was dissolved in dichloromethane, filtered, and the filtrate was washed twice with water. The organic phase was collected, dried, filtered, and the filtrate was concentrated to dryness under reduced pressure to give compound Int.-4, a yellow solid, with a yield of 90%.

[0128] Step 5: Preparation of compound Int.-5

[0129]

[0130] Under nitrogen protection, 20.0 mmol of the previously prepared Int.-4 was mixed with 60 mL of toluene, and then 22.0 mmol of iodobenzene, 80.0 mmol of anhydrous potassium carbonate, 2.0 mmol of cuprous iodide and 5.0 mmol of N,N'-dimethylethylenediamine were added. The mixture was heated to reflux and stirred for 12 hours, then cooled to room temperature, filtered, and the filtrate was concentrated and dried under reduced pressure. The filtrate was purified by silica gel column chromatography to give compound Int.-5 as a yellow solid with a yield of 84%.

[0131] Step 6: Preparation of compound Int.-6

[0132]

[0133] Under nitrogen protection, 20.0 mmol of Int.-5 prepared in the previous step was dissolved in 80 mL of toluene, 0.2 mmol of p-toluenesulfonic acid was added, the mixture was heated to reflux, stirred for 12 hours, cooled to room temperature, 50 mL of water was added, the organic phase was separated, concentrated and dried under reduced pressure, and purified by silica gel column chromatography to obtain compound Int.-6, a white solid, with a yield of 93%.

[0134] Step 7: Preparation of compound Int.-7

[0135]

[0136] Under nitrogen protection, 20.0 mmol of Int.-6 prepared in the previous step was dissolved in 50 mL of DMF, cooled to 0 °C, and 21.0 mmol of NBS was added in portions. The mixture was stirred for 2 hours, and the reaction solution was poured into 150 mL of saturated sodium chloride aqueous solution. The mixture was filtered, the filter cake was washed with water, and the solid was purified by silica gel column chromatography to obtain compound Int.-7, a white solid with a yield of 90%.

[0137] Step 8: Preparation of compound C19

[0138]

[0139] Under nitrogen protection, 22.0 mmol of Int.-7 (reactant 1) prepared in the previous step, 20.0 mmol of sub-1 (reactant 2), 30.0 mmol of sodium tert-butoxide, 0.2 mmol of Pd2(dba)3 and 0.4 mmol of Xantphos were added, followed by 80 mL of toluene. The mixture was heated to 100 °C and stirred for 15 hours. After cooling to room temperature, 50 mL of water was added, and the organic phase was separated. The aqueous phase was extracted with toluene, the organic phase was dried, filtered, and the filtrate was concentrated and dried under reduced pressure. The filtrate was purified by silica gel column chromatography to obtain compound C19.

[0140] X = CPh₂, yellow solid, yield 84%, MS (TOF): m / z 860.3113 [M+H] + ; 1 HNMR (δ, CDCl3): 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); 7.5 3~7.45(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).

[0141] X = O, yellow solid, yield 85%, MS (TOF): m / z 710.2274 [M+H] + ; 1 HNMR (δ, CDCl3): 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).

[0142] Following a similar synthetic method to the above embodiments, the following compounds were prepared:

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153] Example 2

[0154] The preparation method of compound C113 includes the following steps:

[0155] Step 1: Preparation of compound Int.-8

[0156]

[0157] Following the synthesis method of Example 1, except that 3-bromo-2-cyanobenzothiophene in the first step of Example 1 was replaced with 2-iodo-3-cyanobenzothiophene, compound Int.-8 was prepared with a yield of 89%.

[0158] Step 2: Preparation of compound Int.-9

[0159]

[0160] Following the synthesis method of Example 1, only Int.-1 in the second step of Example 1 was replaced with Int.-8 to prepare compound Int.-9, with a yield of 92%.

[0161] Step 3: Preparation of compound Int.-10

[0162]

[0163] 20.0 mmol of the previously prepared Int.-9 was dissolved in 100 mL of methanol, and 0.2 g of 10% palladium / carbon was added. Hydrogen gas was introduced at room temperature and atmospheric pressure, and the mixture was stirred for 12 hours. The mixture was filtered, and the filtrate was concentrated and dried under reduced pressure to give compound Int.-10, a brown solid, with a yield of 100%.

[0164] Step 4: Preparation of compound Int.-11

[0165]

[0166] Under nitrogen protection, 20.0 mmol of Int.-10 prepared in the previous step and 20.0 mmol of diphenylglycolic acid were dissolved in 80 mL of toluene, 0.2 mmol of p-toluenesulfonic acid was added, the mixture was heated to reflux, stirred for 12 hours, cooled to room temperature, 50 mL of water was added, the organic phase was separated, concentrated and dried under reduced pressure, and purified by silica gel column chromatography to give compound Int.-11 as a yellow solid with a yield of 90%.

[0167] Step 5: Preparation of compound Int.-12

[0168]

[0169] Following the synthesis method of Example 1, except that Int.-6 in step 7 of Example 1 was replaced with Int.-11, compound Int.-12 was prepared as a yellow solid with a yield of 93%.

[0170] Step 6: Preparation of compound C113

[0171]

[0172] Under nitrogen protection, 22.0 mmol of the previously prepared Int.-12 (reactant 1), 20.0 mmol of sub-2 (reactant 2), 30.0 mmol of sodium tert-butoxide, 0.2 mmol of Pd2(dba)3, and 0.4 mmol of a 10% tri-tert-butylphosphide toluene solution were added, followed by 80 mL of toluene. The mixture was heated to 100 °C and stirred for 15 hours. After cooling to room temperature, 50 mL of water was added, and the organic phase was separated. The aqueous phase was extracted with toluene, and the organic phase was dried, filtered, and the filtrate was concentrated to dryness under reduced pressure. The filtrate was purified by silica gel column chromatography to give compound C113 as a yellow solid in 83% yield. MS (TOF): m / z 706.2255 [M+H] + ; 1 HNMR (δ, CDCl3): 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); 7.69~7.6 2(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).

[0173] Following a similar synthetic method to the above embodiments, the following compounds were prepared:

[0174]

[0175]

[0176]

[0177]

[0178]

[0179] In the above embodiments, *—X—* is independently selected from *—O—*, *—S—*, or one of the structures shown below:

[0180]

[0181] *— and —* represent connector keys.

[0182] Example 3

[0183] An OLED element 100, such as Figure 1As shown, the OLED element in this embodiment is a top-emitting element, including 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, a cathode 110 disposed on the electron injection layer 109, and a capping layer 111 above the cathode. The method for fabricating an OLED element that does not include the hole blocking layer 107 includes the following steps:

[0184] 1) The glass substrate coated with the ITO conductive layer was ultrasonically treated in the cleaning agent for 30 minutes, rinsed in deionized water, ultrasonically treated in the acetone / ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dry, irradiated with a UV cleaner for 10 minutes, and bombarded with a low-energy cation beam.

[0185] 2) Place the prepared ITO glass substrate into a vacuum chamber and evacuate to a vacuum level less than 1 × 10⁻⁶. -5 Pa, metallic silver is deposited as the anode layer on the above ITO film, and the thickness of the deposited film is [missing information]. Compounds HI01 and HI02 were then deposited separately as hole injection layers, with HI02 accounting for 3% of the mass of HI01, and the deposited film thickness was [missing information].

[0186] 3) The compound HTM is then deposited onto the aforementioned hole injection layer as a hole transport layer, with a deposition thickness of [missing information].

[0187] 4) HTO22 compound is further deposited as an electron blocking layer on the aforementioned hole transport layer, with a film thickness of [missing information].

[0188] 5) The compound of formula (I) of the present invention, RH01 as the host material, and RD030 as the dopant material are further deposited on the electron blocking layer by vapor deposition. The mass ratio of the compound of formula (I) of the present invention to RH01 is 1:1, and RD030 accounts for 5% of the mass of the host material. This serves as the organic light-emitting layer for the device, and the thickness of the vapor-deposited organic light-emitting layer is [missing information].

[0189] 6) A layer of LiQ and compound ETO33 is deposited on the organic light-emitting layer as an electron transport layer for the device, wherein compound ETO33 accounts for 40% of the mass of LiQ, and the deposited film thickness is [missing information].

[0190] 7) A LiF layer is deposited on top of the electron transport layer as an electron injection layer, with a deposition thickness of [missing information].

[0191] 8) A transparent cathode layer of magnesium and silver is deposited on top of the electron injection layer as the element, with a magnesium to silver mass ratio of 1:10, and the deposited film thickness is [missing information].

[0192] 9) A third HTM layer is deposited on top of the transparent cathode layer as the CPL layer for the component, with a deposition thickness of [missing information]. The OLED element of the present invention is obtained.

[0193] The structure of the compound used in Example 3 above is as follows:

[0194]

[0195] Example 4

[0196] An organic electroluminescent element 200, the structure of which is as follows: Figure 2 As shown, it 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. The electroluminescent element 200 is prepared by a similar preparation method as in Example 3.

[0197] Comparative Example 1

[0198] Following the same steps as in Example 3, replace the compound formula shown in (I) of the present invention in step 5) with E01 to obtain comparative element 1;

[0199]

[0200] Under the same brightness, the driving voltage and current efficiency, as well as the lifetime of the organic electroluminescent elements prepared in Examples 3, 4, and Comparative Example 1, were measured using a digital source meter and a luminance meter. Specifically, the voltage was increased at a rate of 0.1V per second, and the measurement was performed when the brightness of the organic electroluminescent element reached 1000 cd / m². 2 The voltage at that time is the driving voltage, and the current density at that time is measured simultaneously; the ratio of brightness to current density is the current efficiency; the LT90% lifespan test is as follows: using a luminance meter at 1000 cd / m² 2 At a constant current under the given brightness, the brightness decay of the organic electroluminescent element was measured to be 900 cd / m². 2 Time is measured in hours. All results are summarized in Table 1. Test results are normalized to the data in Comparative Example 1 (data in parentheses) for ease of comparison.

[0201] Table 1 Performance test results of each component

[0202]

[0203]

[0204]

[0205]

[0206] Wherein, Me is methyl; Ph is phenyl; PhPh is biphenyl; Ad is 2,2-adamantyl; and FR is 9,9-fluorenyl.

[0207] As can be seen from Table 1, the compounds of the present invention, when used as the material of the light-emitting layer, have achieved high-efficiency and long-life organic electroluminescent devices. The devices have low driving voltage, improved current efficiency, and excellent LT90% lifetime, indicating that the compounds of the present invention are high-performance organic electroluminescent materials.

[0208] The difference between compound E01 in Comparative Example 1 and the compound of the present invention lies in the fact that after introducing a triarylamine group into the phenanthreneoxazole of E01, its electron transport capability is weaker than its hole transport capability, resulting in an imbalance in exciton transport within the device, leading to an increase in device driving voltage and a decrease in efficiency. In contrast, the compound of the present invention improves electron transport capability by introducing imidazole or pyrazine groups into dibenzofuran, dibenzothiophene, or carbazole. Therefore, when used with n-type RH01 as the host material, its exciton transport performance is significantly enhanced, resulting in a more balanced exciton transport within the device and a significant improvement in device performance.

[0209] The organic electroluminescent device of the present invention can be used in planar light sources such as wall-mounted televisions, flat panel displays, and lighting, as well as in backlights of copiers, printers, liquid crystal displays, or light sources of measuring instruments, display panels, and indicator lights.

[0210] The above description is merely a specific embodiment of the present invention, but the scope of protection of the present invention is not limited thereto. Any variations or substitutions that can be easily conceived by those skilled in the art within the technical scope disclosed in the present invention should be included within the scope of protection of the present invention. Therefore, the scope of protection of the present invention should be determined by the scope of the claims.

Claims

1. An amino compound, characterized by, The amino compound is selected from the group consisting of the structures C01-C210: wherein each *—X—* is independently selected from *—O—*, *—S—* or one of the following structures: *—and—* represent a bond.

2. An organic electroluminescent material, characterized by The organic electroluminescent material comprises the amino compound of claim 1.

3. An organic electroluminescent device, characterized by comprising The organic electroluminescent device comprises 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 the capping layer comprises the amino compound of claim 1.

4. The organic electroluminescence device according to claim 3, 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 can be one layer, two layers or multiple layers; the hole transport layer or / and the light emitting layer comprises the amino compound of claim 1.

5. A consumer product, characterized in that The organic electroluminescent device comprises the amino compound of claim 1. The organic electroluminescent device comprises the amino compound of claim 1.

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