Amino compound and its application

Abstract

The present invention relates to an amino compound and use thereof. By comprising the amino compound according to the present invention, an organic electroluminescent device having improved driving voltage and / or current efficiency characteristics can be provided.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescence, and specifically relates to an amino compound and application thereof in organic electroluminescent materials and light-emitting elements. Background Art

[0002] Most of the substances used in organic electroluminescent elements are pure organic substances or organic metal complexes formed by organic substances and metals, and can be divided into hole injectors, hole transporters, luminescent substances, electron transporters, electron injectors, etc. according to their uses. Here, organic substances with relatively small ionization energy are mainly used as hole injectors or hole transporters, and organic substances with large electronegativity are mainly used as electron injectors or electron transporters.

[0003] In addition, the material used as the light-emitting auxiliary layer should preferably meet the following characteristics:

[0004] First, the materials used in organic electroluminescent elements need to have good thermal stability. The reason is that Joule heat is generated inside the organic electroluminescent element due to the migration of charges. At present, the glass transition temperature of the materials commonly used as hole transport layers is low. Therefore, when driven at low temperatures, the luminous efficiency decreases due to crystallization. Second, in order to reduce the driving voltage, the organic matter adjacent to the cathode and anode needs to be designed to have a small charge injection barrier and a high charge mobility. Third, there are always energy barriers at the interface between the electrode and the organic layer, and at the interface between the organic layer and the organic layer, and some charges are inevitably accumulated. Therefore, it is necessary to use materials with excellent electrochemical stability.

[0005] An 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 stacked in sequence. When voltage is applied between the positive and negative electrodes, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move to the electroluminescent layer, and the holes on the anode side also move to the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light.

[0006] In the prior art, JP2006083073A, WO2019135665A1, CN1 11213251A, CN111247652A, US20200365814A1, etc. disclose materials that can be used to prepare hole transport layers, auxiliary layers, and light-emitting layers in organic electroluminescent devices. However, it is still necessary to continue to develop new materials to further improve the performance of electronic components. Summary of the invention

[0007] The object of the present invention is to provide an amino compound, an organic electroluminescent material, a light-emitting element and a consumer product for improving the performance of the organic electroluminescent element.

[0008] In order to achieve the above object, the present invention adopts the following technical solution:

[0009] An amino compound, the general structural formula of the amino compound is shown in formula (I):

[0010]

[0011] in,

[0012] R 1 , R 2 , R 3 , R 4 , R 5 are the same or different from each other and each represents one or more to saturated substitutions, each independently selected from hydrogen, deuterium, substituted or unsubstituted C 1 ~C 30 Alkyl, substituted or unsubstituted C 6 ~C 50 Aryl, substituted or unsubstituted C 3 ~C 30 Cycloalkyl, substituted or unsubstituted C 2 ~C 50 Heteroaryl, substituted or unsubstituted C 1 ~C 30 Alkoxy, substituted or unsubstituted C 6 ~C 50 Aryloxy, substituted or unsubstituted C 1 ~C 30 Alkylthio, substituted or unsubstituted C 6 ~C 50 Arylthio, substituted or unsubstituted C 1 ~C 30 Alkylamino, substituted or unsubstituted C 6 ~C 50 Arylamine, substituted or unsubstituted C 1 ~C 30 Alkylsilyl, substituted or unsubstituted C 6 ~C 50 A group consisting of an arylsilyl group, a cyano group, or a halogen atom, any two or more adjacent R 1 ~R 5 They may be arbitrarily joined or fused to form a substituted or unsubstituted ring, and the formed ring may contain or not contain heteroatoms N, O, S, P, B, Si or Se, and in R 2 and R3 At least one of them is a group represented by formula (II) or formula (III);

[0013]

[0014] L 1 , L 2 are each independently selected from a single bond, a substituted or unsubstituted C 6 ~C 50 Arylene, substituted or unsubstituted C 2 ~C 50 The group consisting of heteroarylene;

[0015] m and n are each independently selected from integers of 0 to 5;

[0016] Ar 1 ,Ar 2 ,Ar 3 are each independently selected from substituted or unsubstituted C 6 ~C 50 Aryl, substituted or unsubstituted C 6 ~C 50 Arylamine, substituted or unsubstituted C 10 ~C 50 Fused aromatic, substituted or unsubstituted C 2 ~C 50 The group consisting of heteroaryl;

[0017] Dashed lines represent the attachment sites of the groups.

[0018] The alkyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a straight or branched saturated hydrocarbon having a carbon number of 1 to 30. Non-limiting examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, and the like;

[0019] The aryl group in the sense of the present invention contains 6 to 50 carbon atoms, and the heteroaryl group contains 2 to 50 carbon atoms and at least one heteroatom, provided that the total number of carbon atoms and heteroatoms 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 attached to each other simply or in a condensed form, and further, can also include a condensed form with the aryl group. As non-limiting examples of aryl and heteroaryl groups, in particular, the following groups are selected: phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, pyrenyl, yl, peryl, fluoranthene, tetraphenyl, pentacene, benzopyrenyl, biphenyl, phenylene, terphenyl, triphenyl, quadriphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, triphenylene, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, cis- or trans-indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzocarbazolyl, dibenzocarbazolyl, azadibenzo[g,Id]naphtho[2,1,8-cde]azulenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, spiroisotrimerized indenyl, furanyl, benzofuranyl, isobenzofuranyl , dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo[5,6]quinolyl, benzo[6,7]quinolyl, benzo[7,8]quinolyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, isoxazolyl, 1,2 -thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, hexaazatriphenylene radical, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluorescein ring radical, naphthyridinyl, azacarbazolyl, benzocarbolinyl, carbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 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-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, quinazolinyl, benzothiadiazolyl or a group derived from a combination of these systems.

[0020] The "halogen" or "halogen atom" used in the present invention refers to a group selected from fluorine, chlorine, bromine or iodine.

[0021] Furthermore, the amino compound is selected from the group consisting of the following structures:

[0022]

[0023]

[0024] Among them, R 1 ~R 5 , L 1 , L 2 ,Ar 1 ,Ar 2 and Ar 3 The meaning is the same as defined above.

[0025] Furthermore, m and n are each independently selected from 0, 1 or 2.

[0026] Furthermore, the R 1 , R 2 , R 3 , R 4 , R 5 each independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl, isobutyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted The invention also comprises a group consisting of a substituted or unsubstituted peryl group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophene group.

[0027] Furthermore, the Ar 1 ,Ar 2 ,Ar 3 Each of the following is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted benzanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted The invention also comprises a group consisting of a substituted or unsubstituted perylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0028] Furthermore, the Ar 3 Selected from the group consisting of the following groups II-1 to II-13:

[0029]

[0030] in,

[0031] Z 1 , Z 2 Each is independently selected from hydrogen, deuterium, halogen, hydroxyl, nitrile, nitro, amino, amidine, hydrazine, hydrazone, carboxyl or its carboxylate, sulfonic acid or its sulfonate, phosphoric acid or its phosphate, C 1 -C 40 Alkyl, C 2 -C 40 Alkenyl, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy, C 3 -C 40 Cycloalkane, C 3 -C 40 Cycloalkene, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Aryl thioether, substituted or unsubstituted C 6 -C 60 Arylamine, or substituted or unsubstituted C 2 -C 60 The group consisting of heteroaryl;

[0032] x1 represents an integer from 1 to 4; x2 represents an integer from 1 to 3; x3 represents 1 or 2; x4 represents an integer from 1 to 6; x5 represents an integer from 1 to 5;

[0033] T 1 indicates O, S or NAr';

[0034] Ar' is selected from C 1 ~C 40 Alkyl, C 1 ~C 40 Heteroalkyl, C 3 ~C 40 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 10 -C 60 Condensed ring aromatic group, substituted or unsubstituted C 6 -C 60 Arylamine, or substituted or unsubstituted C 2 -C 60The group consisting of heteroaryl; preferably, Ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;

[0035] Indicates the attachment site of a group.

[0036] The heteroalkyl group in the sense of the present invention refers to a hydrogen atom or a -CH 2 - is substituted by at least one heteroatom selected from halogen, nitrile, N, O, S or silicon, as non-limiting examples, there are difluoromethyl, trifluoromethyl, trifluoroethyl, pentafluoroethyl, nitrile, acetonitrile, methoxymethyl, methoxyethyl, trimethylsilyl, triisopropylsilyl, etc. Haloalkyl means that the hydrogen atoms on the alkyl are partially or fully substituted by halogen, as non-limiting examples, there are fluorotoluene, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoroethyl, pentafluoroethyl, etc.

[0037] The alkenyl or alkynyl group used in the present invention contains at least two carbon atoms. As non-limiting examples, alkenyl or alkynyl is preferably taken to mean the following groups: cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.

[0038] The alkoxy or alkylthio groups used in the present invention are preferably alkoxy or alkylthio groups having 1 to 40 carbon atoms, and are considered to be methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio 4-(2-(4-(2-methyl-1-thio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1,4-dithio)-1

[0039] Generally speaking, the cycloalkyl and cycloalkenyl groups according to the present invention can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, wherein one or more -CH 2 - group can be replaced by N, O or S to form heterocycloalkyl, heterocycloalkenyl, for example, one -CH 2- group is replaced by O to form a -CH in tetrahydrofuranyl or cyclohexyl 2 - group is replaced by O to form a tetrahydropyranyl group, etc.; in addition, one or more hydrogen atoms may be replaced by a deuterium atom, a halogen atom or a nitrile group.

[0040] The aryloxy group used in the present invention refers to a monovalent functional group represented by R'O-, wherein R' is an aryl group having a carbon number of 6 to 60. Non-limiting examples of such aryloxy groups include phenoxy, naphthoxy, biphenyloxy and the like.

[0041] The arylthio group used in the present invention refers to a monovalent functional group represented by R"S-, wherein R" is an aryl group having 6 to 60 carbon atoms. Non-limiting examples of such arylthio groups include phenylthio, naphthylthio, biphenylthio and the like.

[0042] The alkylsilyl used in the present invention refers to a silyl group substituted by an alkyl group having 1 to 40 carbon atoms, and the number of carbon atoms constituting the alkylsilyl group is at least 3. Non-limiting examples of the alkylsilyl group include trimethylsilyl and triethylsilyl. The arylsilyl group refers to an alkylsilyl group substituted by at least one aryl group having 6 to 60 carbon atoms, and non-limiting examples include phenyldimethylsilyl, naphthyldimethylsilyl, phenyldiethylsilyl, diphenylmethylsilyl, diphenylethylsilyl, triphenylsilyl, and the like.

[0043] "Alkylcarbonyl", "alkoxycarbonyl", "arylcarbonyl", "arylborylcarbonyl" and "alkylborylcarbonyl" in the sense of the present invention refer to a substituted carbonyl group (-COR*), wherein R* is preferably selected from the group consisting of alkyl, alkoxy, cycloalkyl, aryl, heteroaryl, arylboryl and alkylboryl.

[0044] The arylphosphino group used in the present invention refers to a diarylphosphino group substituted with an aryl group having 6 to 60 carbon atoms, and non-limiting examples of the arylphosphino group include diphenylphosphino group, di(4-trimethylsilylphenyl)phosphino group, etc. The aryloxyphosphino group is a diarylphosphino group in which the phosphorus atom is oxidized to the highest valence state.

[0045] The aryl boryl group used in the present invention refers to a diaryl boryl group substituted by an aryl group having 6 to 60 carbon atoms, and non-limiting examples of the aryl boryl group include diphenyl boryl and di(2,4,6-trimethylphenyl)boryl. The alkyl boryl group refers to a dialkyl boryl group substituted by an alkyl group having 1 to 40 carbon atoms, and non-limiting examples of the alkyl boryl group include di-tert-butyl boryl and diisobutyl boryl.

[0046] The arylalkyl group according to the present invention refers to an alkyl group in which at least one hydrogen atom of a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms is substituted by an aryl group having 6 to 60 carbon atoms, and as non-limiting examples, may be phenylmethyl, diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, etc.

[0047] The alkylaryl group according to the present invention refers to an aryl group having 6 to 60 carbon atoms in which at least one hydrogen atom is substituted by a straight-chain or branched saturated hydrocarbon having 1 to 40 carbon atoms. As non-limiting examples, it may be methylphenyl, dimethylphenyl, trimethylphenyl, tert-butylphenyl, isopropylphenyl, etc.

[0048] The substituents of the substituted alkyl, substituted aryl, substituted heteroaryl, substituted arylamine, substituted fused aryl, substituted arylene, and substituted heteroarylene described in the present invention are each independently selected from at least one of the following groups: 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 with one or more C 6 -C 60 3- to 30-membered heteroaryl substituted with aryl, unsubstituted or substituted with deuterium, one or more C 1 -C 40 alkyl and at least one of 3- to 30-membered heteroaryl groups substituted with 6 -C 60 Aryl, tri(C 1 -C 40 ) alkylsilyl, tri(C 6 -C 60 )Arylsilyl, di(C 1 -C 4 0) alkyl (C 6 -C 60 )Arylsilyl, C1 -C 40 Alkyl di(C 6 -C 60 )Arylsilyl, C 1 -C 40 Alkylcarbonyl, C 1 -C 40 Alkoxycarbonyl, C 6 -C 60 Arylcarbonyl, di(C 6 -C 60 ) arylboronic acid, di(C 1 -C 40 ) alkyl boron carbonyl, C 1 -C 40 Alkyl (C 6 -C 6 0) Aryl boron carbonyl, C 6 -C 60 Aryl (C 1 -C 4 0) alkyl, and C 1 -C 40 Alkyl (C 6 -C 60 )aryl.

[0049] The arylene group in the present invention refers to a divalent functional group obtained by removing two hydrogen atoms from an aromatic hydrocarbon having a carbon number of 6 to 60. Non-limiting examples thereof include phenylene, naphthylene, phenanthrylene, anthrylene, fluorenylene, and spirobifluorenylene.

[0050] The heteroarylene group or heteroarylene group in the present invention refers to a divalent functional group obtained by removing two hydrogen atoms from a heteroaromatic hydrocarbon having a carbon number of 2 to 60. Non-limiting examples thereof include pyridylene, quinolylene, isoquinolylene, carbolylene, pyrimidylene, triazinylene and the like.

[0051] According to the above-mentioned arylene and heteroarylene as divalent functional groups and NAr 1 Ar 2 Connect or with Ar 3 connection, preferably, the L 1 , L 2 Each is independently selected from a single bond or the group consisting of the following groups shown in III-1 to III-24:

[0052]

[0053] Wherein, X is selected from O, S, S e , CR'R", SiR'R" or NAr'

[0054] Z 11 , Z 12, Z 13 , Z 14 Each is independently selected from hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, an amidine group, a hydrazine group, a hydrazone group, a carboxyl group or a carboxylate thereof, a sulfonic acid group or a sulfonate thereof, a phosphoric acid group or a phosphate thereof, a C 1 -C 60 Alkyl, C 2 -C 60 The alkenyl group, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Cycloalkane, C 3 -C 60 Cycloalkene, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 aryl thioether group, or substituted or unsubstituted C 2 -C 60 The group consisting of heteroaryl;

[0055] y1 represents an integer of 1-4; y2 represents an integer of 1-6; y3 represents an integer of 1-3; y4 represents an integer of 1-5; y5 represents 1 or 2;

[0056] R', R" are each independently selected from C 1 -C 60 Alkyl, C 1 -C 60 Heteroalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamine, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups, R' and R" may be optionally joined or fused to form one or more additional substituted or unsubstituted rings, containing or not containing one or more heteroatoms N, P, B, O or S in the formed rings; preferably, R', R" are methyl, phenyl or fluorenyl;

[0057] Ar' is selected from C 1 -C 60 Alkyl, C 1 -C 60 Heteroalkyl, C 3 -C 60 Cycloalkyl, substituted or unsubstituted C6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aromatic group, substituted or unsubstituted C 6 -C 60 Arylamine, or substituted or unsubstituted C 2 -C 60 The group consisting of heterocyclic aromatic groups; preferably, Ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;

[0058] The dashed lines represent the attachment sites of the groups.

[0059] Preferably, X is selected from O or S.

[0060] Furthermore, the L 1 , L 2 Selected from a single bond or a group consisting of the following groups III-1 to III-15 and III-24:

[0061]

[0062]

[0063] Preferably, the Z 11 , Z 12 , Z 13 , Z 14 Each is independently selected from the group consisting of hydrogen, deuterium, fluorine, and nitrile.

[0064] Furthermore, the amino compound is selected from one or more of the following structures B100 to B231:

[0065]

[0066]

[0067]

[0068]

[0069] Wherein, *-G-* is independently selected from *-O-*, *-S-* or one of the following structures:

[0070]

[0071] *- and -* represent connection keys.

[0072] As used herein, "combinations thereof" or "groups" means that one or more members of the applicable list are combined to form known or chemically stable arrangements that can be envisioned 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 alkyls; halogens and alkyls can be combined to form haloalkyl substituents, such as trifluoromethyl, etc.; and halogens, alkyls, and aryls can be combined to form haloaralkyls.

[0073] An organic electroluminescent material, comprising the amino compound; the organic electroluminescent material comprising the amino compound of the invention has the ability of carrier transport.

[0074] The organic electroluminescent material may be composed of the amino compound of the present invention alone, or may contain other compounds simultaneously.

[0075] 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.

[0076] The present invention also provides the use of the amino compound mentioned above in preparing an organic electroluminescent element.

[0077] The present invention also provides an organic electroluminescent element, which comprises: 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 layer and the CPL layer comprises the amino compound described above.

[0078] The organic electroluminescent element comprises a cathode, an anode, a CPL and at least one luminescent layer. In addition to these layers, it may also comprise other 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 generation layers. An intermediate layer having, for example, an exciton blocking function may also be introduced between two luminescent layers. However, it should be noted that each of these layers does not necessarily have to be present. The organic electroluminescent element described herein may comprise one luminescent layer, or it may comprise multiple luminescent layers. That is, a variety of luminescent compounds capable of luminescence are used in the luminescent layer. A system having three luminescent layers is particularly preferred, wherein the three layers can display blue, green and red luminescence. If there are more than one luminescent layer, then according to the present invention, at least one of these layers comprises a compound of the present invention.

[0079] 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.

[0080] In the other layers of the organic electroluminescent element according to the invention, in particular in the hole transport layer and in the emitting layer and in the CPL layer, all materials can be used in the manner commonly used according to the prior art. A person skilled in the art will therefore be able to use all materials known about organic electroluminescent elements in combination with the emitting layer according to the invention without inventive effort.

[0081] Generally speaking, an OLED includes at least one organic layer disposed between and electrically connected to an anode and a cathode. Figure 1 A schematic diagram of an organic light-emitting device 100 is shown. The illustration is 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 manufactured by depositing the described layers in order.

[0082] Figure 2 A schematic diagram of an organic light-emitting device 200 containing 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 prepared by depositing the layers described in sequence. Because the most common OLED device has a single-color light-emitting layer or a light-emitting layer having three primary colors, the device 200 has two light-emitting layers of the same light color. In the corresponding layers of the device 200, materials similar to those described with respect to the device 100 can be used. Figure 2 One example is provided of how some layers may be added from the structure of device 100 .

[0083] Figure 1 and Figure 2The simple layered structure illustrated in is provided as a non-limiting example, and it should be understood that embodiments of the present invention can be used in conjunction with a variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures can be used. Functional OLEDs can be achieved by combining the various layers described in different ways, or several layers can be omitted entirely, based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials different from those specifically described may be used. Although many of the examples provided herein describe various layers as including a single material, it will be understood that combinations of materials, such as a mixture of a matrix and a dopant, or more generally, a mixture, can be used. Also, the layers may have various sub-layers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 204 transports holes and injects holes into light-emitting layer 205, and may be described as a hole transport layer or an electron blocking layer. In one embodiment, the OLED may be described as having an organic layer disposed between a cathode and an anode. This organic layer may include a single layer or may further include, for example Figure 1 and Figure 2 Multiple layers of different organic materials are described.

[0084] Structures and materials not specifically described may also be used, such as PLEDs comprising polymer materials. As another example, an OLED having a single organic layer or multiple stacks may be used. The OLED structure may be separated from Figure 1 and Figure 2 For example, the substrate may include angled reflective surfaces to improve light coupling.

[0085] On the other hand, the organic electroluminescent device of the present invention can be manufactured by forming the organic layer and the electrode using materials and methods known in the art, except that at least one of the organic layers contains the amino compound described above.

[0086] In addition, the material that can be used as the anode contained in the organic electroluminescent element according to the present invention is not particularly limited. As non-limiting examples, metals such as vanadium, chromium, copper, zinc, gold, aluminum, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO:Al or SnO 2 : Combinations of metals such as Sb and oxides; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline; and carbon black, etc.

[0087] The substance that can be used as the cathode contained in the organic electroluminescent element according to the present invention is not particularly limited. As non-limiting examples, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or their alloys can be used; and LiF / Al or Li 2 O / Al and other multilayer structure materials.

[0088] The material that can be used as the substrate included in the organic electroluminescent element according to the present invention is not particularly limited, and as non-limiting examples, a silicon wafer, quartz, a glass plate, a metal plate, or a plastic film and sheet can be used.

[0089] Furthermore, preference is given to organic electroluminescent components in which one or more layers can be applied by means of a sublimation process, in which the organic electroluminescent components are deposited in a vacuum sublimation apparatus at temperatures below 10 -5 Pa, preferably less than 10 -6 The material is applied by vapor deposition at an initial pressure of 10 Pa. However, the initial pressure may also be even lower, for example below 10 -7 Pa.

[0090] Likewise preferred are organic electroluminescent elements in which one or more layers can also be applied by means of an organic vapor phase deposition method or by means of carrier gas sublimation, wherein in the range of 10 to 200 nm, 5 The material is applied at a pressure of between 100 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 thus structured.

[0091] In addition, organic electroluminescent elements are preferably used in which one or more layers are produced from a solution, for example by spin coating, or by any desired printing method, for example screen printing, flexographic printing, lithography, photoinduced thermography, thermal transfer, inkjet printing or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution of the compounds of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Also possible are hybrid methods, in which, for example, one or more layers are applied from a solution and one or more further layers are applied by vapor deposition.

[0092] These methods are generally known to those skilled in the art, and they can apply them to organic electroluminescent elements comprising the compounds according to the invention without inventive step.

[0093] Therefore, the present invention also relates to a method for producing an organic electroluminescent element according to the present 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 vapor deposition method or by means of carrier gas sublimation and / or applying at least one layer from a solution by spin coating or by means of a printing method.

[0094] In addition, the present invention relates to compounds of the present invention comprising at least one indicated above. The same preferences as indicated above for organic electroluminescent elements apply to the compounds of the present invention. In particular, the compounds may also preferably comprise other compounds. Processing the compounds of the present invention from the liquid phase, for example by spin coating or by a printing method, requires preparations for processing the compounds of the present invention, which preparations may be, for example, solutions, dispersions or emulsions. For this purpose, a mixture of two or more solvents may preferably be used. 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, (-)-fennel, 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, α-terpenes benzothiazole, butyl benzoate, isopropylbenzene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-cymene, 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, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, or a mixture of these solvents.

[0095] 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.

[0096] Furthermore, the hole transport layer, the light emitting layer, or the CPL layer comprises the amino compound of the present invention.

[0097] A consumer product made from the organic electroluminescent device, wherein the consumer product comprises the organic electroluminescent device provided by the present invention.

[0098] The consumer product described in the present invention can be one of the following products: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior lighting and / or signaling, heads-up displays, fully 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, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple displays tiled together, theater or stadium screens, light therapy devices and signage.

[0099] In addition, unless otherwise specified, the raw materials used in the present invention can be obtained commercially, and any range recorded in the present invention includes the end value and any numerical value between the end values ​​and any sub-range formed by the end value or any numerical value between the end values.

[0100] The present invention also relates to a mixture comprising at least one compound of formula (I) or the above preferred embodiments and at least one other compound. If the compound according to the present invention is used as a matrix material, the other compound may be a fluorescent or phosphorescent emitter. The mixture may then also contain other materials as additional matrix materials. The present invention also relates to the use of the compound according to the present invention in electronic components. Preferably, as mentioned above, the compound according to the present invention is used in a hole transport layer or as a matrix material in a light-emitting layer. The compounds according to the present invention and the electronic components, in particular organic electroluminescent components, which can be obtained therefrom are distinguished from the prior art by one or more of the following surprising advantages:

[0101] The amino compound described in the present invention has a novel rigid structure of substituted phenanthrene and carbazole with a large planar conjugation. As for the compound represented by the general formula (I) of the present invention, it has the following characteristics: (1) large carrier mobility; (2) high internal quantum efficiency; (3) stable thin film state; and (4) excellent heat resistance. Therefore, it is suitable for use as a constituent material of the light-emitting layer of the organic electroluminescent element of the present invention.

[0102] As for the organic electroluminescent element of the present invention which uses the amino compound represented by the above-mentioned general formula (I) of the present invention as the main material of the light-emitting layer, since a compound having a carrier mobility greater than that of previous materials, a high internal quantum efficiency, excellent amorphous properties, and a stable thin film state is used, it is possible to realize an organic electroluminescent element with high efficiency, low driving voltage, and long life.

[0103] Furthermore, in the present invention, by forming a light-emitting layer with the amino compound of the general formula (I), the high quantum efficiency and heat resistance of the compound can be effectively utilized to the maximum extent, and an organic electroluminescent element with higher efficiency and longer life can be realized.

[0104] In addition, in the present invention, with respect to the organic electroluminescent element of the present invention which uses the amino compound represented by the above-mentioned general formula (I) as its constituent material in at least any one layer of the above-mentioned light-emitting layer or a stacked film having two or more light-emitting layers, since a compound having high carrier mobility, high internal quantum efficiency, excellent amorphous property and stable thin film state is used, it is possible to realize an organic electroluminescent element with high efficiency, low driving voltage and long life.

[0105] The advantages mentioned above are not accompanied by a reduction in other electronic properties.

[0106] 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 the present invention may be replaced by an alternative feature having the same, equivalent or similar purpose unless expressly excluded. Therefore, unless otherwise stated, each feature disclosed in the present invention should be regarded as an example of a generic series or an equivalent or similar feature.

[0107] All features of the present invention can be combined with each other in any way, unless specific features and / or steps are mutually exclusive. This is particularly applicable to the preferred features of the present invention. Similarly, features that are not necessarily combined can be used alone (and not in combination). It should also be noted that many features, particularly the features of the preferred embodiments of the present invention, are creative in themselves and should not be considered as only part of the embodiments of the present invention. For these features, independent protection may be sought in addition to or as a substitute for each invention currently claimed.

[0108] The teaching 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 it is not intended to limit the present invention. Based on the description, those skilled in the art will be able to perform the present invention within the disclosed entire scope, and will not pay creative work and will be able to prepare other compounds of the present invention and use them in electronic components, or use method of the present invention. BRIEF DESCRIPTION OF THE DRAWINGS

[0109] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings required for use in the embodiments or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.

[0110] Figure 1 A schematic diagram of an organic light-emitting device 100 is shown. The illustration is 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 manufactured by depositing the described layers in order.

[0111] Figure 2 Schematic diagram of an organic light-emitting device 200 showing 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 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 prepared by depositing the described layers in sequence. Because the most common OLED device has one light-emitting layer, and the device 200 has a first light-emitting layer and a second light-emitting layer, the light emission peaks of the first light-emitting layer and the second light-emitting layer can be overlapping, cross-overlapping, or non-overlapping. In the corresponding layers of the device 200, materials similar to those described with respect to the device 1 can be used. Figure 2 One example is provided of how some layers may be added from the structure of device 100 . DETAILED DESCRIPTION

[0112] To make the purpose, technical solution and advantages of the present invention clearer, the technical solution of the present invention will be described in detail below. Obviously, the described embodiments are only part of the embodiments of the present invention, rather than all the embodiments. Based on the embodiments of the present invention, all other implementation methods obtained by ordinary technicians in this field without creative work belong to the scope of protection of the present invention.

[0113] In the present invention, the preparation methods are conventional methods unless otherwise specified. The raw materials used can be obtained from public commercial channels unless otherwise specified, and the percentages are mass percentages unless otherwise specified. In the series of novel organic compounds provided by the present invention, all reactions are carried out under well-known suitable conditions, and some involve simple organic preparations, such as the preparation of phenylboronic acid derivatives, which can be synthesized by skilled operation skills and are not described in detail in the present invention.

[0114] Any range described in the present invention includes the end value and any numerical value between the end values ​​and any sub-range formed by the end value or any numerical value between the end values.

[0115] The test instruments and methods for testing the performance of OLED materials and components in the following embodiments are as follows:

[0116] OLED component performance testing conditions:

[0117] Brightness and chromaticity coordinates: tested using a spectral scanner PhotoResearch PR-715;

[0118] Current density and lighting voltage: tested using Keithley 2420 digital source meter;

[0119] Power efficiency: tested using NEWPORT 1931-C;

[0120] Life test: Use LTS-1004AC life test device.

[0121] Example 1

[0122] The preparation method of compound B100 comprises the following steps:

[0123] Step 1: Preparation of compound Int-1

[0124]

[0125] Under nitrogen protection, 21.0 mmol of Sub-0, 20.0 mmol of o-bromophenylacetylene, 60 mL of 1,4-dioxane and 20 mL of triethylamine were mixed, and 4.0 mmol of cuprous iodide and 4.0 mmol of PdCl were added. 2 (PPh 3 ) 2 The catalyst was added, the temperature was raised to reflux and stirred for reaction for 10 hours, the mixture was cooled to room temperature, concentrated under reduced pressure, and purified by silica gel column to obtain compound Int-1 as a yellow solid. The yield was 64%.

[0126] Step 2: Preparation of compound Int-2

[0127]

[0128] Under nitrogen protection, 20.0 mmol of Int-1 prepared in the previous step, 60.0 mmol of copper chloride, 10.0 mmol of anhydrous potassium phosphate and 60 mL of nitromethane were mixed, the temperature was raised to reflux and stirred for reaction for 10 hours, cooled to room temperature, filtered, the filtrate was concentrated to dryness under reduced pressure, and separated and purified by silica gel column to obtain compound Int-2 as a white solid with a yield of 87%.

[0129] Step 3: Preparation of compound Int-3

[0130]

[0131] Under nitrogen protection, 20.0 mmol of Int-2 prepared in the previous step was dissolved in 50 mL of dry THF, cooled to -78°C, and 24.0 mmol of 2.5 M n-butyl lithium n-hexane solution was added dropwise, stirred for reaction for 1 hour, and then 30.0 mmol of trimethyl borate was added dropwise, stirred for reaction for 1 hour, warmed to room temperature, and 20 mL of 3 M dilute hydrochloric acid aqueous solution was added. The organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The organic phase was collected, dried, filtered, and the filtrate was concentrated under reduced pressure to dryness, dispersed with n-pentane, filtered, and the filter cake was washed with n-pentane to obtain compound Int-3 as a yellow solid with a yield of 85%.

[0132] Step 4: Preparation of compound Int-4

[0133]

[0134] Under nitrogen protection, 22.0 mmol of Int-3 prepared in the previous step, 20.0 mmol of 1-bromocarbazole and 50 mL of methanol benzene were mixed, and then 50.0 mmol of sodium carbonate and 0.2 mmol of Pd(PPh 3 ) 4 Catalyst, 30 mL of ethanol and 30 mL of water were heated to reflux and stirred for reaction for 10 hours, cooled to room temperature, extracted with ethyl acetate, the organic phase was collected, dried, filtered, and the filtrate was concentrated to dryness under reduced pressure. The compound Int-4 was obtained as a yellow solid with a yield of 85%.

[0135] Step 5: Preparation of compound Int-5

[0136]

[0137] Under nitrogen protection, 30.0 mmol of 85% potassium hydroxide was dissolved in 50 mL of DMSO, stirred for reaction for 1 hour, 20.0 mmol of Int-4 prepared in the previous step was added, the temperature was raised to 120°C, stirred for reaction for 12 hours, cooled to room temperature, the reaction solution was poured into 150 mL of ice water, filtered, the filter cake was washed with water, and the solid was separated and purified by silica gel column to obtain compound Int-5 as a yellow solid with a yield of 87%.

[0138] Step 6: Preparation of compound Int-6

[0139]

[0140] Under nitrogen protection, 20.0 mmol of Int-5 prepared in the previous step was dissolved in 50 mL of dichloromethane, cooled to 0°C, 30.0 mmol of boron tribromide was added dropwise, stirred for 2 hours, 50 mL of ice water was added, the organic phase was separated, the aqueous phase was extracted with dichloromethane, the organic phase was collected, dried, filtered, and the filtrate was concentrated under reduced pressure and purified by silica gel column to obtain compound Int-6 as a yellow solid with a yield of 98%.

[0141] Step 7: Preparation of compound Int-7

[0142]

[0143] Under nitrogen protection, 20.0 mmol of Int-6 prepared in the previous step and 50.0 mmol of pyridine were dissolved in 50 mL of dichloromethane, cooled to 0°C, 30.0 mmol of trifluoromethanesulfonic anhydride was added dropwise, warmed to room temperature, stirred for 2 hours, 50 mL of ice water was added, the organic phase was separated, the aqueous phase was extracted with dichloromethane, the organic phase was collected, dried, filtered, and the filtrate was concentrated under reduced pressure and purified by silica gel column to obtain compound Int-7 as a yellow solid with a yield of 92%.

[0144] Step 8: Preparation of Compound B100

[0145]

[0146] Under nitrogen protection, 22.0 mmol of Int-7 prepared in the previous step (reactant 1), 20.0 mmol of N-phenyl-[1,1′-biphenyl]-4-amine (reactant 2), 30.0 mmol of sodium tert-butoxide, 2.0 mmol of cuprous iodide, 0.2 mmol of Pd 2 (dba) 3 and 0.4 mmol of Xantphos, and then 60 mL of toluene was added, the temperature was raised to 110°C, stirred and reacted for 15 hours, cooled to room temperature, 50 mL of water was added, the organic phase was separated, the aqueous phase was extracted with dichloromethane, the organic phase was dried, filtered, the filtrate was concentrated under reduced pressure, and separated and purified by silica gel column to obtain compound B100 as a yellow solid with a yield of 85%. MS (TOF): m / z 661.2583 [M+H] + .

[0147] Example 2 to Example 102

[0148] The following compounds were prepared by similar synthetic methods to those in the above examples:

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158] Embodiment 103

[0159] The preparation method of compound B208 comprises the following steps:

[0160] Step 1: Preparation of compound Int-8

[0161]

[0162] Under nitrogen protection, 20.0 mmol of Int-7' (reactant 1), 24.0 mmol of biboric acid pinacol ester and 60 mL of 1,4-dioxane were mixed, and then 20.0 mmol of potassium iodide and 2.0 mmol of PdCl were added. 2 (dppf) catalyst and 30.0 mmol of potassium acetate, heat to reflux and stir to react for 12 hours, cool to room temperature, concentrate under reduced pressure, and separate and purify with silica gel column to obtain compound Int-8 as a yellow solid. Yield: 86%.

[0163] Step 2: Preparation of compound B208

[0164]

[0165] Under nitrogen protection, 22.0mmol of Int-8 prepared in the previous step, 20.0mmol of 2-chloro-4,6-diphenyl-1,3,5-triazine (reactant 2), 50.0mmol of anhydrous potassium carbonate and 40mL of toluene were mixed, and then 0.01mmol of Pd132, 20mL of ethanol and 20mL of water were added. The temperature was raised to reflux and stirred for reaction for 15 hours, cooled to room temperature, 50mL of water was added, the organic phase was separated, the aqueous phase was extracted with ethyl acetate, the organic phase was collected, dried, filtered, and the filtrate was concentrated under reduced pressure and purified by silica gel column to obtain compound B208 as a white solid with a yield of 78%. MS (TOF): m / z 649.2326 [M+H] + .

[0166] Embodiment 104 to Embodiment 133

[0167] The following compounds were prepared by similar synthetic methods to those in the above examples:

[0168]

[0169]

[0170]

[0171] In the above embodiments, *-G-* is independently selected from *-O-*, *-S-* or one of the following structures:

[0172]

[0173] Application Example 1

[0174] An OLED element 100, such as Figure 1 As shown, the OLED element of this embodiment is a top emission element, comprising 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 on the cathode. The preparation method of the OLED element without the hole blocking layer 107 comprises the following steps:

[0175] 1) The glass substrate coated with the ITO conductive layer was ultrasonically treated in a cleaning agent for 30 minutes, rinsed in deionized water, ultrasonically treated in an acetone / ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dry, irradiated with an ultraviolet cleaning machine for 10 minutes, and bombarded with a low-energy cation beam.

[0176] 2) Place the treated ITO glass substrate in a vacuum chamber and evacuate the chamber to a vacuum of less than 1×10 -5 Pa, and silver is evaporated on the above ITO as an anode, and the thickness of the evaporated film is Continue to evaporate the compounds DNTPD and F4TCNQ as the hole injection layer, F4TCNQ is 3% of the mass of DNTPD, and the evaporated film thickness is

[0177] 3) On the hole injection layer film, a layer of the compound represented by formula I of the present invention is continuously deposited as a hole transport layer, and the thickness of the deposited film is

[0178] 4) Continue to evaporate a layer of compound HT202 on the hole transport layer as an electron blocking layer, and the evaporated film thickness is

[0179] 5) A layer of compound BH345 and BD035 is continuously evaporated on the electron blocking layer as an organic light-emitting layer, wherein BD035 is a doping material and compound BH345 is a main material, the doping concentration of compound BD035 in BH345 is 8%, and the evaporated film thickness is

[0180] 6) A layer of compound LiQ and ET212 is further evaporated on the above-mentioned light-emitting layer as the electron transport layer of the device, wherein the mass ratio of LiQ to ET212 is 1:1, and the evaporated film thickness is

[0181] 7) A layer of compound LiF is further evaporated on the above electron transport layer as the electron injection layer of the device, and the evaporated film thickness is

[0182] 8) On the electron injection layer, magnesium and silver are evaporated as the cathode layer of the element. The mass ratio of magnesium to silver is 1:10 and the thickness of the evaporated film is

[0183] Finally, the same compound as in step 3) is deposited on the cathode as a capping layer of the element, and the thickness of the deposited film is

[0184] The structures of the compounds used in the above application examples are as follows:

[0185]

[0186] Comparative Example 1

[0187] The same steps as in Application Example 1 are followed, except that compound H01 is used instead of the compound of formula I in step 3) of Application Example 1 and in the final capping layer. The structure of compound H01 is:

[0188]

[0189] The organic electroluminescent elements prepared in the above application examples and comparative examples were tested, and the specific testing method is as follows:

[0190] Specifically, the driving voltage was increased at a rate of 0.1 B per second, and the brightness of the organic electroluminescent element was measured to reach 1000 cd / m 2The voltage at which the light is on is the driving voltage, and the current density at this time is measured at the same time; the ratio of brightness to current density is the current efficiency; the LT90% life test is as follows: use a brightness meter at 1000cd / m 2 At the same brightness, the current is kept constant and the brightness decay of the organic electroluminescent element is measured to be 900cd / m 2 All the results are summarized in Table 2, and the test results are normalized based on the data of Comparative Example 1 (data in brackets) for easy comparison.

[0191] Table 2 Performance test results of each component

[0192]

[0193]

[0194]

[0195]

[0196] As can be seen from Table 2, the compounds of the present invention are used as materials for the hole transport layer and the capping layer to obtain an organic electroluminescent element with high efficiency and long life, the element has low driving voltage, improved current efficiency, and excellent LT90% life.

[0197] The difference between the compound H01 in comparative example 1 and the compound of the present invention is that the steric hindrance of the biphenyl group at the 10th position of phenanthrene increases the steric hindrance of the diphenylamine group at the 9th position, which is not conducive to the close stacking of molecules. The compound of the present invention, phenanthrene and carbazole, form a large planar conjugated structure with small steric hindrance, so it has excellent performance in molecular film formation and carrier transmission, the transmission of excitons in the device is more balanced, and the device performance is improved.

[0198] The organic electroluminescent device of the present invention can be used in planar light emitters of wall-mounted televisions, flat-panel displays, lighting, etc., backlight sources of copiers, printers, liquid crystal displays, light sources of measuring instruments, etc., display panels, sign lights, etc.

[0199] The above is only a specific embodiment of the present invention, but the protection scope of the present invention is not limited thereto. Any person skilled in the art can easily think of changes or substitutions within the technical scope disclosed by the present invention, which should be included in the protection scope of the present invention. Therefore, the protection scope of the present invention should be based on the protection scope of the claims.

Claims

1. An amino compound, It is characterized in that The amino compound is selected from the group consisting of the following structures: 、 、 、 、 、 、 、 、 、 、 、 ； Among them, R 1 ~R 5 All are hydrogen; L 1 , L 2 are each independently selected from a single bond or a phenyl group; Ar 1 ,Ar 2 Each is independently selected from the group consisting of phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, triphenylene, anthracenyl, benzanthryl, pyrenyl, chrysyl, peryl, fluoranthenyl, carbazolyl, fluorenyl, indolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, or dibenzothiophene; m and n are each independently selected from 0 or 1; The Ar 3 Selected from the group consisting of: 、 ； in, Z 1 Selected from the group consisting of hydrogen, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, carbazolyl, dibenzothienyl, or dibenzofuranyl; x2 represents an integer from 1 to 3; x3 represents 2; Indicates the attachment site of a group.

2. An amino compound, It is characterized in that The amino compound is selected from the group consisting of the structures shown in B100 to B231: Wherein, *—G—* are each independently selected from *—O—*, *—S—* or one of the following structures: 、 、 、 、 、 、 、 、 ； *— and —* represent connecting keys.

3. An organic electroluminescent material, It is characterized in that The organic electroluminescent material comprises the amino compound according to any one of claims 1 to 2.

4. An organic electroluminescent device, It is characterized in that 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 according to any one of claims 1 to 2.

5. The organic electroluminescent device according to claim 4, It is characterized in that The organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; the amino compound is in the hole transport layer or in the capping layer.

6. A consumer product, It is characterized in that The organic electroluminescent device according to claim 4 is included.

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