CN111675713B

CN111675713B - Arylamine compound and organic light-emitting device thereof

Info

Publication number: CN111675713B
Application number: CN202010709378.4A
Authority: CN
Inventors: 周雯庭; 孙月; 杜明珠; 苗玉鹤
Original assignee: Changchun Hyperions Technology Co Ltd
Current assignee: Changchun Hyperions Technology Co Ltd
Priority date: 2020-07-22
Filing date: 2020-07-22
Publication date: 2021-11-02
Anticipated expiration: 2040-07-22
Also published as: CN111675713A

Abstract

The invention provides an arylamine compound and an organic light-emitting device thereof, belonging to the technical field of organic photoelectric materials. The arylamine compound is a compound formed by using the superlattice alkali as a mother nucleus and using a dibenzothiophene/dibenzofuran/carbazole or fluorene substituted arylamine structure as a substituent group, has good hole transport performance and good thermal stability, is a hole transport material with excellent performance, can be used as a hole transport layer material when being applied to an organic light-emitting device, and has good luminous efficiency and lower driving voltage.

Description

Arylamine compound and organic light-emitting device thereof

Technical Field

The invention relates to the technical field of organic photoelectric materials, in particular to an arylamine compound and an organic light-emitting device thereof.

Background

An organic light-emitting device (OLED) is a flat panel all-solid-state display technology developed in the eighties of the twentieth century. The working principle is that the organic luminescent material is driven by an electric field to form excitons through carrier injection, transmission and recombination and the excitons decay to emit light. Compared with the traditional display technology, the OLED has the following characteristics: (1) the main active material adopts organic matter, so the material has wide selection range and can realize the luminescence of any color from red light to blue light; (2) the energy consumption is low, the driving voltage is low (only 3-12V direct current voltage is needed generally); (3) the luminous brightness is high, the viewing angle is wide, and the response speed is high; (4) ultra-thin, light-weight, fully cured active luminescence; (5) the display device can be manufactured on a flexible substrate, and the device can be bent and folded, and can also realize transparent display; (6) wide temperature range of operation, etc. Due to the above technical advantages, the OLED is considered as the mainstream of the next generation display technology, and has attracted wide attention from the academic and industrial circles at home and abroad.

Current research into improving the performance of OLEDs includes: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. This requires innovation in device structure and manufacturing process, and creation of higher performance organic light emitting materials. For example, as a hole transport material, a material is required to have not only good carrier mobility but also good thermal stability and the like.

Therefore, aiming at the current industrial application requirements of the OLED and the photoelectric characteristic requirements of the device, the comprehensive characteristics of high efficiency and low voltage of the device can be realized only by selecting more suitable organic light-emitting materials with better performance, such as hole transport layer materials with better hole transport performance and stronger thermal stability. In terms of the actual demand of the current OLED display illumination industry, the development of the organic light emitting material is far from enough, and lags behind the requirements of panel manufacturing enterprises, and it is very important to develop a higher-performance organic light emitting material as a material enterprise.

Disclosure of Invention

The invention aims to provide an arylamine compound and an organic light-emitting device thereof.

The invention provides an arylamine compound, which has a structure shown in a chemical formula 1:

in the chemical formula 1, the first and second,

Ar₁～Ar₄at least one selected from the group consisting of structures represented by chemical formula 2:

the rest is one of substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted heteroaryl of C2-C30,

X₁selected from O, S, N-R₁、C-R₂R₃One of (1); r₁One selected from aryl of C6-C18 and heteroaryl of C2-C20; r₂、R₃Independently selected from one of C1-C10 alkyl, C6-C18 aryl, or R₂、R₃Can be bonded with each other to form a ring;

ring A is selected from no or benzene ring;

L₁、L₂、L_aindependently selected from a single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C2-C30;

R_a、R_b、R₄independently selected from one of hydrogen, deuterium, halogen, cyano, C1-C10 alkyl and C6-C12 aryl;

m is an integer from 0 to 3; n is an integer from 0 to 3; y is selected from an integer of 0 to 3;

in the "substituted or unsubstituted", the substituent is selected from one or more of deuterium, halogen, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, tolyl, cumyl, tert-butylphenyl, mesityl, pentadeuterophenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylene, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, benzospirobifluorenyl, carbazolyl, 9-phenylcarbazolyl, 1-phenylindolyl, phenoxazinyl, phenothiazinyl, dibenzofuranyl, dibenzothienyl; when the substituent is plural, plural substituents are the same as or different from each other; when the substituent is plural, adjacent substituents may be bonded to each other to form a ring.

The present invention also provides an organic light emitting device comprising a cathode, an anode, and one or more organic layers disposed between or outside the cathode and anode; the organic layer comprises at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a covering layer; the organic layer contains any one or the combination of at least two of arylamine compounds.

The invention has the beneficial effects that: the arylamine compound provided by the invention is a super-Grignard base

base, TB for short) as a mother nucleus, and dibenzothiophene/dibenzofuran/carbazole or fluorene substituted arylamine structure as a substituent group. The TB structure has a special rigid inverted V-type kinking configuration, the special steric hindrance skeleton bridge can obviously reduce the aggregation state fluorescence quenching phenomenon of the material, the stability of the compound is improved, the dibenzothiophene/dibenzofuran/carbazole or fluorene substituted arylamine structure is introduced, the electron donating capability of the compound is further enhanced, the hole fluidity is improved, the dibenzothiophene/dibenzofuran/carbazole or fluorene rigid condensed ring structure has good coplanarity, the thermal stability of the compound is further improved, and the arylamine compound has good thermal stability and hole transmission performance and is a good hole transmission material; the arylamine compound provided by the invention can be applied to an organic light-emitting device and can be used as a hole transport layer material, and the organic light-emitting device prepared by adopting the arylamine compound provided by the invention has good luminous efficiency and lower driving voltage.

Description of the drawings:

FIG. 1 is a drawing showing Compound 1 of the present invention¹H NMR chart; FIG. 2 is a drawing showing Compound 17 of the present invention¹H NMR chart;

FIG. 3 is a drawing of Compound 38 of the present invention¹H NMR chart; FIG. 4 shows Compound 56 of the present invention¹H NMR chart;

FIG. 5 shows a scheme for preparing a compound 81 of the present invention¹H NMR chart; FIG. 6 is a drawing of Compound 107 of the present invention¹H NMR chart;

FIG. 7 shows a scheme for preparing a compound 149 of the present invention¹H NMR chart; FIG. 8 is a drawing showing a preparation of compound 159 of the present invention¹H NMR chart;

FIG. 9 is a drawing of compound 163 of the present invention¹H NMR chart; FIG. 10 shows a scheme for preparing a compound 167 according to the invention¹H NMR chart.

The specific implementation mode is as follows:

the following will clearly and completely describe the technical solutions of the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the scope of protection of the present invention.

in the chemical formula 1, the first and second,

ring A is selected from no or benzene ring;

The arylene group in the present invention refers to a divalent group remaining after two hydrogen atoms have been removed from the aromatic core carbon of the aromatic hydrocarbon molecule, preferably having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms, and the arylene group may be substituted or unsubstituted. Examples may include phenylene, biphenylene, terphenylene, etc., naphthylene, anthracenylene, triphenylene, pyrenylene, fluorenylene, peryleneene, fluorenylene, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirofluorenyl, benzofluorenyl, etc., but are not limited thereto. The arylene group is preferably a phenylene group, a biphenylene group, a terphenylene group, or the like, a naphthylene group, an anthracenylene group, a triphenylene group, a pyrenylene group, a fluorenylene group, a 9, 9-dimethylfluorenyl group, a 9, 9-diphenylfluorenyl group, a spirofluorenyl group, or a benzofluorenyl group.

Heteroarylene as used herein refers to a group in which one or more of the aromatic core carbons in the arylene group is replaced with a heteroatom, including but not limited to oxygen, sulfur, nitrogen, silicon, preferably having from 2 to 30 carbon atoms, more preferably from 2 to 20 carbon atoms, particularly preferably from 3 to 12 carbon atoms, and most preferably from 3 to 8 carbon atoms, which heteroarylene group may be substituted or unsubstituted. Examples may include, but are not limited to, pyridylene, pyrimidylene, triazinylene, indolyl, carbazolyl, furanylene, thiophenylene, quinolylene, isoquinolylene, dibenzofuranylene, dibenzothiophenylene, phenothiazinylene, phenoxazylene, and the like. The heteroarylene group is preferably an indolyl group, a carbazolyl group, a furanylene group, a thienyl group, a dibenzofuranylene group, a dibenzothienyl group, a phenothiazinylene group, or a phenoxazylene group.

The alkyl group in the present invention refers to a hydrocarbon group obtained by dropping one hydrogen atom from an alkane molecule, and may be a straight-chain alkyl group, a branched-chain alkyl group, or a cyclic alkyl group, and preferably has 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms, and particularly preferably 1 to 4 carbon atoms, and examples thereof may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a cyclopentyl group, a cyclohexyl group, and the like, but are not limited thereto. The alkyl group is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a tert-butyl group, a cyclopentyl group, or a cyclohexyl group.

The aryl group in the present invention means a monovalent group remaining after one hydrogen atom is removed from an aromatic nucleus carbon of an aromatic hydrocarbon molecule, preferably having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms, and the aryl group may be substituted or unsubstituted. Examples may include phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, pyrenyl, and the like,

Perylene, indenyl, anthryl, fluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirofluorenyl, benzofluorenyl, and the like, but are not limited thereto. The aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a triphenylene group, a fluorenyl group, a 9, 9-dimethylfluorenyl group, a 9, 9-diphenylfluorenyl group, a spirofluorenyl group, or a benzofluorenyl group.

The heteroaryl group in the present invention refers to a group in which one or more aromatic core carbons in an aryl group are replaced with a heteroatom including, but not limited to, oxygen, sulfur, nitrogen, silicon atoms, preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 12 carbon atoms, and most preferably 3 to 8 carbon atoms, and the heteroaryl group may be substituted or unsubstituted. Examples may include, but are not limited to, pyrrolyl, imidazolyl, oxazolyl, thiazolyl, pyridyl, pyrimidinyl, triazinyl, thienyl, furyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, carbazolyl, 9-phenylcarbazolyl, benzimidazolyl, benzoxazolyl, benzothienyl, benzofuryl, dibenzofuryl, dibenzothienyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, and the like. The heteroaryl group is preferably a thienyl group, furyl group, indolyl group, carbazolyl group, benzothienyl group, benzofuryl group, dibenzofuryl group or dibenzothienyl group.

In the "substituted or unsubstituted" of the present invention, the substituents are independently selected from deuterium, cyano, nitro, halogen atom, alkyl group of C1 to C10, alkoxy group of C1 to C10, alkylthio group of C1 to C10, aryl group of C6 to C30, aryloxy group of C6 to C30, arylthio group of C6 to C30, heteroaryl group of C3 to C30, silyl group of C1 to C30, alkylamino group of C2 to C10, arylamine group of C6 to C30, or a combination of the above groups, for example: deuterium, cyano group, nitro group, halogen, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, methoxy group, methylthio group, phenyl group, pentadeuterated phenyl group, biphenyl group, terphenyl group, naphthyl group, anthryl group, phenanthryl group, benzophenanthryl group, triphenylene group, perylenyl group, pyrenyl group, fluorenyl group, 9-dimethylfluorenyl group, 9-dibenzofluorenyl group, spirobifluorenyl group, benzospirobifluorenyl group, tolyl group, cumenyl group, tert-butylphenyl group, phenoxy group, thiophenyl group, dianilinyl group, dimethylamino group, carbazolyl group, furyl group, thienyl group, dibenzofuryl group, dibenzothienyl group, triphenylsilyl group, trimethylsilyl group, trifluoromethyl group, phenothiazinyl group, phenoxazinyl group, acridinyl group, pyridyl group, pyrazinyl group, triazinyl group, pyrimidinyl group, etc., however, the substituents are not limited thereto, and may be other than those listed above as long as the technical effects of the present invention can be achieved. The substituent may be one or more, and when the substituent is plural, plural substituents are the same as or different from each other; when the substituent is plural, adjacent substituents may be bonded to each other to form a ring.

The phrase "may be bonded to each other to form a ring" as used herein means that two groups are bonded to each other by a chemical bond. The ring formed by bonding may be a three-or four-or five-or six-membered ring or a fused ring, such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, benzene, naphthalene, anthracene, quinoline, isoquinoline, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto. The ring formed by the above linkage is preferably benzene or naphthalene.

Preferably, the arylamine compound is selected from any one of the following structures:

preferably, Ar is₁～Ar₄At least one of which is selected from one of the structures shown below:

the others are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, and substituted or unsubstituted

A group, a substituted or unsubstituted perylene group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted pyridyl groupSubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.

Preferably, Ar is₁One selected from the structures shown below:

preferably, L_aOne selected from single bond, phenylene, tolylene and biphenylene;

R₁one selected from phenyl, tolyl, biphenyl and naphthyl; r₂、R₃Independently selected from hydrogen, methyl, ethyl, phenyl, or R2, R3 may be bonded to each other to form a ring;

R₄one selected from hydrogen, deuterium, methyl, ethyl, phenyl, tolyl, pentadeuterated phenyl and biphenyl;

y is selected from an integer of 0 to 4;

preferably, Ar is₂～Ar₄Independently selected from any one of the structures shown below:

preferably, R₅One selected from the group consisting of hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, tolyl, cumyl, tert-butylphenyl, mesityl, pentadeuterophenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylene, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, benzospirobifluorenyl, carbazolyl, 9-phenylcarbazolyl, 1-phenylindolyl, phenoxazinyl, phenothiazinyl, dibenzofuranyl, and dibenzothienyl;

p is selected from an integer of 0 to 5; q is an integer selected from 0 to 4; r is selected from 0 or 1;

R₆one selected from phenyl, tolyl, biphenyl and naphthyl.

preferably, L₁、L₂Independently selected from one of single bond, phenylene, tolylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrylene, pyridylene, 9-dimethylfluorenyl, 9-diphenylfluorenyl, carbazolyl, dibenzofuranylene and dibenzothiophenyl.

Preferably, L₁、L₂Independently selected from a single bond or any one of the structures shown as follows:

preferably, R_a、R_bIndependently selected from one of hydrogen, methyl, ethyl, isopropyl, tert-butyl, phenyl, tolyl, biphenyl and naphthyl.

some specific structural forms of the arylamine compound of the present invention are listed above, but the present invention is not limited to these listed chemical structures, and all the substituents are the groups as defined above based on the structure shown in chemical formula 1.

The arylamine compound can be prepared by the following synthetic route, but the invention is not limited to the following synthetic route:

starting materials 1-j and 2-j in (CH)₂O)_nAnd TFA to obtain intermediate of chemical formula 1-a.

When L is₁、L₂And a single bond, chemical formula 1 is represented by chemical formula 1',

the intermediate chemical formula 1-a and the raw material 1-k are subjected to Buchwald reaction to obtain an intermediate chemical formula 1-b.

The intermediate chemical formula 1-b and the raw material 2-k undergo Buchwald reaction to obtain chemical formula 1'.

When L is₁、L₂When the aryl is arylene or heteroarylene,

the intermediate chemical formula 1-a and the raw material 1-h are subjected to Suzuki reaction to obtain an intermediate chemical formula 1-c;

the intermediate chemical formula 1-c and the raw material 2-h are subjected to Suzuki reaction to obtain the chemical formula 1.

When L is₁、L₂One is arylene, heteroarylene, and the other is a single bond, which can be obtained by combining the above methods.

The synthesis reaction of the present invention is not particularly limited in terms of reaction conditions and raw materials required for the reaction, and may be a commercially available product or a preparation method known to those skilled in the art.

The invention also provides an organic light-emitting device which comprises a cathode, an anode and one or more organic layers arranged between and outside the cathode and the anode, wherein the organic layer contains any one or the combination of at least two of the arylamine compounds.

The organic layer comprises at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a covering layer. However, the structure of the organic light emitting device of the present invention is not limited to the above structure, and a plurality of organic layers may be omitted or simultaneously provided, if necessary. For example, an electron blocking layer may be further provided between the hole transport layer and the light emitting layer, and a hole blocking layer may be further provided between the electron transport layer and the light emitting layer; the organic layers having the same function may be formed in a stacked structure of two or more layers.

Any material commonly used in the art can be used for the other layers except that the hole transport layer in the organic light emitting device contains any one or a combination of at least two of any of the aromatic amine compounds described in the present invention.

In the organic light emitting device of the present invention, the anode material may be selected from metals, such as copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, and the like, and alloys thereof; metal oxides such as indium oxide, zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), aluminum zinc oxide, and the like; examples of the conductive polymer include polyaniline, polypyrrole, and poly (3-methylthiophene). In addition to the above materials and combinations thereof, the anode material may also include other known materials suitable for use as an anode.

In the organic light emitting device according to the present invention, the hole injection material may be selected from molybdenum oxide, silver oxide, vanadium oxide, tungsten oxide, ruthenium oxide, nickel oxide, copper oxide, metal oxides such as titanium oxide, copper phthalocyanine (CuPc), 4',4 ″ -tris [ 2-naphthylphenylamino ] triphenylamine (2T-NATA), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylamine (HAT-CN), 4',4 ″ -tris (N, N-diphenylamino) triphenylamine (TDATA), N ' -bis [4- [ bis (3-methylphenyl) amino ] phenyl ] -N, N ' -diphenyl-biphenyl-4, 4' -diamine (DNTPD), and the like. In addition to the above materials and combinations thereof, the hole injection material may include other known materials suitable for use as a hole injection layer.

In the organic light emitting device of the present invention, the hole transport material may be selected from any one of the aromatic amine compounds described in the present invention or a composition containing any one of the aromatic amine compounds described in the present invention.

In the organic light emitting device of the present invention, the light emitting layer material includes a light emitting layer host material AND a light emitting layer guest material, AND the light emitting layer host material may be selected from 4,4 '-bis (9-Carbazole) Biphenyl (CBP), 9, 10-bis (2-naphthyl) Anthracene (ADN), 4-bis (9-carbazolyl) biphenyl (CPB), 9' - (1, 3-phenyl) bis-9H-carbazole (mCP), 4',4 ″ -tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (1-naphthyl) anthracene (α -AND), N' -bis- (1-naphthyl) -N, N '-diphenyl- [1,1':4',1": 4', 1' -quaterphenyl.]-4,4' -diamino (4PNPB), 1,3, 5-tris (9-carbazolyl) benzene (TCP), and the like. In addition to the above materials and combinations thereof, the light emitting layer host material may also include other known materials suitable for use as a light emitting layer. The guest materials of the light-emitting layer of the invention are divided into blue light-emitting materials, green light-emitting materials and red light-emitting materials. The light-emitting layer guest can be selected from (6- (4- (diphenylamino (phenyl) -N, N-diphenylpyren-1-amine) (DPAP-DPPA), 2,5,8, 11-tetra-tert-butylperylene (TBPe), 4' -bis [4- (diphenylamino) styryl]Biphenyl (BDAVBi), 4' -bis [4- (di-p-tolylamino) styryl]Biphenyl (DPAVBi), bis (2-hydroxyphenyl)Beryllium (Bepp2), bis (4, 6-difluorophenylpyridine-C2, N) picolinoylium (FIrpic), tris (2-phenylpyridine) iridium (Ir (ppy)₃) Bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy)₂(acac)), 9, 10-bis [ N- (p-tolyl) anilino group]Anthracene (TPA), 4- (dicyanomethylene) -2-methyl-6- (4-dimethylaminostyryl) -4H-pyran (DCM), tris [ 1-phenylisoquinoline-C2, N]Iridium (III) (Ir (piq)₃) Bis (1-phenylisoquinoline) (acetylacetonato) iridium (Ir (piq))₂(acac)) and the like. In addition to the above materials, the light-emitting layer guest material may include other known materials suitable for use as a light-emitting layer.

In the organic light emitting device of the present invention, the doping ratio of the host material and the guest material in the light emitting layer is determined according to the materials used. Preferably, the doping film thickness ratio of the guest material of the light-emitting layer is 0.5-10%.

In the organic light emitting device of the present invention, the electron transport material may be selected from 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), tris (8-hydroxyquinoline) aluminum (III) (Alq)₃) 8-hydroxyquinoline-lithium (Liq), bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq), 3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), and the like, and the electron transport material may include other known materials suitable for an electron transport layer in addition to the above materials and combinations thereof.

In the organic light emitting device according to the present invention, the electron injection material may Be selected from Li, Na, K, Rb, Cs, Be, Mg, Ca, lithium fluoride (LiF), sodium fluoride, potassium fluoride, rubidium fluoride, cesium fluoride, magnesium fluoride, calcium fluoride, lithium oxide, cesium carbonate, potassium silicate, lithium acetate, sodium acetate, potassium acetate, lithium tetrakis (8-hydroxyquinoline) boron, lithium 8-hydroxyquinoline, and the like, and in addition to the above materials and combinations thereof, the electron injection material may include other known materials suitable for an electron injection layer.

In the organic light emitting device of the present invention, the cathode material may be selected from metals such as aluminum, magnesium, silver, indium, tin, titanium, etc. and alloys thereof; multilayer metal materialMaterials such as LiF/Al, Mg/Ag, Li/Al, LiO₂/Al、BaF₂Al, etc. In addition to the above materials and combinations thereof, the cathode material may also include other known materials suitable for use as a cathode.

In the organic light emitting device of the present invention, the material of the cap layer may be selected from tris (8-hydroxyquinoline) aluminum (III) (Alq)₃) 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), and the like, and the cover layer material may include other known materials suitable for the cover layer in addition to the above materials and combinations thereof.

The thickness of each organic layer of the organic light emitting device is not particularly limited in the present invention, and may be any thickness commonly used in the art.

The organic light-emitting device can be prepared by various methods such as solution coating such as ink-jet printing, spin coating and screen printing, vacuum evaporation and the like.

The starting materials used in the following examples are not particularly limited in their source, and may be commercially available products or prepared by methods known to those skilled in the art.

The mass spectrum of the compound of the invention uses AXIMACFRplus matrix assisted laser desorption ionization flight mass spectrometer of Kratos Analytical company of Shimadzu corporation, and chloroform is used as a solvent;

elemental analysis using a Vario EL cube type organic element analyzer of Elementar corporation, Germany, the sample mass was 5 mg;

nuclear magnetic resonance (¹HNMR) Using a Bruker-510 type nuclear magnetic resonance spectrometer (Bruker, Germany), 600MHz, CDCl₃As solvent, TMS as internal standard.

EXAMPLE 1 Synthesis of Compound 1

Synthesis of intermediate a-1:

to a 500ml three-necked flask was added 200ml of TFA at-15 ℃ and j-1(17.27g, 100.4mmol), (CH) was added successively under vigorous stirring₂O)_n(6.12g, 204mmol), the mixed solution was stirred for 20min to room temperature and stirring was continued for 48 h. Ice and excess NH were added slowly at 0 deg.C₃(25% aqueous solution) to the mixture, stirring, over CH₂Cl₂Extraction, MgSO₄After drying, the mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent cyclohexane: ethyl acetate: 10:1) to obtain intermediate a-1 (purity of solid by HPLC ≧ 99.3%, 10.07g, yield 53%).

Mass spectrum m/z: 377.94 (calculated value: 379.93). Theoretical element content (%) C₁₅H₁₂Br₂N₂: c, 47.40; h, 3.18; br, 42.05; n, 7.37. Measured elemental content (%): c, 47.36; h, 3.17; br, 42.07; and N, 7.40. The above results confirmed that the obtained product was the objective intermediate.

Synthesis of Compound 1:

under the protection of nitrogen, the intermediate a-1(7.60g, 20mmol) and 300ml of toluene are added into a 500ml three-neck flask, and the raw material k-1(11.15g, 43mmol) and Pd are added₂(dba)₃(0.55g，0.6mmol)，P(t-Bu)₃(0.2g, 2mmol), sodium tert-butoxide (5.77g, 60 mmol). The reaction was carried out for 4 hours at reflux temperature by nitrogen substitution three times. After the reaction is finished, passing through CH₂Cl₂Extraction, MgSO₄After drying, the mixture was concentrated in vacuo. The residue was subjected to silica gel column chromatography (eluent: cyclohexane: ethyl acetate: 10:1) and recrystallization (solvent: toluene) to obtain compound 1 (purity ≧ 99.5% by HPLC, 11.05g, yield 75%).

Mass spectrum m/z: 737.29 (calculated value: 736.28). Theoretical element content (%) C₅₁H₃₆N₄O₂: c, 83.13; h, 4.92; n, 7.60; and O, 4.34. Measured elemental content (%): c, 82.79; h, 5.11; n, 7.67; and O, 4.42.¹H NMR(600MHz,CDCl₃) (δ, ppm): 7.99-7.93 (m,2H), 7.58-7.51 (m,4H), 7.50-7.41 (m,4H),7.35(td,2H), 7.27-7.17 (m,6H), 7.11-7.04 (m,4H),7.00(tt,2H), 6.96-6.93 (m,1H),6.83(dd,1H), 6.77-6.71 (m,2H), 6.63-6.56 (m,2H),5.41(s,2H),4.61(d, 4H). The above results confirmed that the obtained product was the objective product.

EXAMPLE 2 Synthesis of Compound 17

Compound 17 was obtained according to the method for synthesizing Compound 2 by replacing the equimolar amount of the starting material k-17 with the starting material k-1 in example 1 (purity of solid by HPLC ≧ 99.7%, 11.23g, yield 73%).

Mass spectrum m/z: 769.24 (calculated value: 768.24). Theoretical element content (%) C₅₁H₃₆N₄S₂: c, 79.66; h, 4.72; n, 7.29; s, 8.34. Measured elemental content (%): c, 79.60; h, 4.73; n, 7.31; and S, 8.36.¹H NMR(600MHz,CDCl₃) (δ, ppm): 8.44-8.40 (m,2H),8.02(dt,2H),7.98(d,2H),7.83(dd,2H),7.55(tt,2H), 7.32-7.28 (m,4H), 7.26-7.22 (m,4H), 7.09-7.02 (m,4H),7.00(tt,2H), 6.98-6.95 (m,1H), 6.76-6.73 (m,1H),6.64(dd,2H),6.60(d,1H),6.58(dd,1H),5.41(s,2H),4.61(d, 4H). The above results confirmed that the obtained product was the objective product.

EXAMPLE 3 Synthesis of Compound 38

Synthesis of intermediate k-38:

under the protection of nitrogen, a 500ml three-neck flask is added with the raw material k-38-1(15.89g, 40mmol) and the toluene 300ml, and the raw material k-38-2(3.73g, 40mmol) and PdCl are added₂(dppf)(0.51g，0.7mmol)，P(t-Bu)₃(0.2g, 2mmol), sodium tert-butoxide (5.77g, 60 mmol). The reaction was carried out for 4 hours at reflux temperature by nitrogen substitution three times. After the reaction is finished, passing through CH₂Cl₂Extraction, MgSO₄After drying, the mixture was concentrated in vacuo. The residue was subjected to silica gel column chromatography (eluent: cyclohexane: ethyl acetate: 10:1) and recrystallization (solvent: toluene) to obtain intermediate k-38 (purity ≧ 99.1% by HPLC, 12.61g, yield 77%).

Mass spectrum m/z: 409.18 (calculated value: 411.19). Theoretical element content (%) C₃₁H₂₃N：C，90.92; h, 5.66; and N, 3.42. Measured elemental content (%): c, 90.89; h, 5.71; n, 3.41. The above results confirmed that the obtained product was the objective intermediate.

Synthesis of compound 38:

compound 38 was obtained according to the method for synthesizing Compound 1 by replacing the equimolar amount of the starting material k-38 with the starting material k-1 in example 1 (purity of solid by HPLC ≧ 99.6%, 14.73g, yield 71%).

Mass spectrum m/z: 1038.46 (calculated value: 1036.45). Theoretical element content (%) C₇₇H₅₆N₄: c, 89.16; h, 5.44; and N, 5.40. Measured elemental content (%): c, 89.19; h, 5.44; n, 5.37.¹H NMR(600MHz,CDCl₃) (δ, ppm): 9.95-9.94 (m,2H), 9.94-9.85 (m,2H),9.09(dd,1H),8.70(dd,1H),8.54-8.48(m,2H),8.27(td,1H), 7.96-7.91 (m,7H), 7.80-7.76 (m,2H), 7.66-7.61 (m,2H), 7.60-7.48 (m,8H), 7.26-7.09 (m,10H), 7.08-7.02 (m,4H),6.99(tt,2H),6.61(dd,1H),6.30(dd,1H),6.17(d,1H), 6.05-5.80 (m,1H),5.80(d,1H),5.75(d,1H),5.41(s, 4H), 4.61(d, 1H). The above results confirmed that the obtained product was the objective product.

EXAMPLE 4 Synthesis of Compound 56

Synthesis of compound 56:

compound 56 was obtained by the method for synthesizing Compound 1 by replacing the raw material k-1 in example 1 with an equimolar amount of the raw material k-56 (purity of solid by HPLC ≧ 99.5%, 13.35g, yield 68%).

Mass spectrum m/z: 983.22 (calculated value: 980.21). Theoretical element content (%) C₆₃H₄₀N₄S₄: c, 77.11; h, 4.11; n, 5.71; and S, 13.07. Measured elemental content (%): c, 77.32; h, 4.16; n, 5.63; and S, 12.89.¹H NMR(600MHz,CDCl₃)(δ，ppm)：10.99(d,1H),9.10(dd,1H),8.47-8.46(m,1H),8.43(dd,1H),8.32-8.26(td,1H),8.24(td,1H),8.19(dd,1H),8.08–7.99(m,5H),7.90-7.85(m,2H),7.74(d,1H),7.69(dd,1H),7.68(dd,1H), 7.61-7.52 (m,4H),7.46-7.41(m,1H),7.32(td,1H),7.31(td,4H),6.99(q,1H),6.80-6.76(m,2H),6.62(d,1H),6.31(dd,1H),6.09(dd,1H),5.86(dd,1H),5.41(s,2H),4.61(d, 4H). The above results confirmed that the obtained product was the objective product.

EXAMPLE 5 Synthesis of Compound 81

Synthesis of compound 81:

compound 81 was obtained according to the method for synthesizing Compound 1 by replacing the raw material k-1 in example 1 with an equimolar amount of the raw material k-81 (purity of solid by HPLC ≧ 99.7%, 13.13g, yield 74%).

Mass spectrum m/z: 888.38 (calculated value: 886.38). Theoretical element content (%) C₆₃H₄₆N₆: c, 85.30; h, 5.23; and N, 9.47. Measured elemental content (%): c, 85.51; h, 5.17; and N, 9.32.¹H NMR(600MHz,CDCl₃) (δ, ppm): 9.14(dd,2H),8.35(dd,1H),8.21(dd,1H), 8.20-8.11 (m,2H),7.97(d,1H),7.90(dd,1H),7.70(dd,2H),7.60(t,4H),7.48(dd,1H), 7.37-7.16 (m,12H),7.15(dd,1H), 7.08-7.01 (m,4H),7.00(tt,2H),6.69(dd,1H),6.61(d,1H),6.60(dd,1H), 6.31-6.29 (m,1H),6.17(d,1H),5.88(d,1H),5.41(s,2H),4.61(d, 4H). The above results confirmed that the obtained product was the objective product.

EXAMPLE 6 Synthesis of Compound 107

Synthesis of intermediate k-107:

the intermediate k-107 was obtained by the method for synthesizing the intermediate k-47, which comprises replacing the raw material k-47-1 with the raw material k-107-1 and the raw material k-47-2 in example 3 with the raw material k-107-1 in equimolar amounts (purity by HPLC ≧ 99.1%, 11.55g, yield 79%).

Mass spectrum m/z: 367.08 (calculated value: 365.09). Theoretical element content (%) C₂₄H₁₅NOS: c, 78.88; h, 4.14; n, 3.83; o, 4.38; s, 8.77. Measured elemental content (%): c, 79.06; h, 4.11; n, 3.81; o, 4.39; and S, 8.63. The above results confirmed that the obtained product was the objective intermediate.

Synthesis of compound 107:

compound 107 was obtained according to the method for synthesizing Compound 1 by replacing the equimolar amount of the starting material k-107 with the starting material k-1 in example 1 (purity of solid by HPLC ≧ 99.6%, 14.24g, yield 75%).

Mass spectrum m/z: 949.26 (calculated value: 948.26). Theoretical element content (%) C₆₃H₄₀N₄O₂S₂: c, 79.72; h, 4.25; n, 5.90; o, 3.37; and S, 6.76. Measured elemental content (%): c, 79.72; h, 4.25; n, 5.90; o, 3.37; and S, 6.76.¹H NMR(600MHz,CDCl₃) (δ, ppm): 10.34(d,1H),8.73(dd,1H),8.57(dd,1H),8.45(dd,1H),8.36-8.34(m,2H),8.20(dd,1H),7.94(dd,1H),7.86(dd,2H),7.75(td,1H),7.66(td,1H), 7.64-7.55 (m,4H),7.54(dd,2H), 7.49-7.41 (m,6H),7.35-7.32(m,4H),7.15(dd,1H),6.76(dd,1H),6.57(d,1H),6.29(dd,1H),6.10(d,1H),5.84(d,1H),5.41(s,2H),4.61(d, 4H). The above results confirmed that the obtained product was the objective product.

EXAMPLE 7 Synthesis of Compound 149

Synthesis of intermediate c-149:

under the protection of nitrogen, a 500ml three-neck flask is added with raw material a-1(15.20g, 40mmol) and toluene 300ml, and added with raw material k-149-1(10.37g, 40mmol), PdCl₂(dppf)(0.51g，0.7mmol)，P(t-Bu)₃(0.2g, 2mmol), sodium tert-butoxide (5.77g, 60 mmol). The reaction was carried out for 4 hours at reflux temperature by nitrogen substitution three times. After the reaction is finished, passing through CH₂Cl₂Extraction, MgSO₄After drying, the mixture was concentrated in vacuo. The residue was subjected to silica gel column chromatography (eluent: cyclohexane: ethyl acetate ═ 10:1) and recrystallization (solvent: toluene) to give intermediate c-149 (solid detected by HPLC)Purity ≧ 99.3%, 14.52g, yield 65%).

Mass spectrum m/z: 558.11 (calculated value: 557.11). Theoretical element content (%) C₃₃H₂₄BrN₃O: c, 70.97; h, 4.33; br, 14.31; n, 7.52; o, 2.86. Measured elemental content (%): c, 70.87; h, 4.39; br, 14.33; n, 7.52; o, 2.88. The above results confirmed that the obtained product was the objective intermediate.

Synthesis of compound 149:

under the protection of nitrogen, a 500ml three-neck flask is charged with the raw material k-17(11.01g, 40mmol), toluene 300ml, and the intermediate c-149(22.34g, 40mmol), PdCl₂(dppf)(0.51g，0.7mmol)，P(t-Bu)₃(0.2g, 2mmol), sodium tert-butoxide (5.77g, 60 mmol). The reaction was carried out for 4 hours at reflux temperature by nitrogen substitution three times. After the reaction is finished, passing through CH₂Cl₂Extraction, MgSO₄After drying, the mixture was concentrated in vacuo. The residue was subjected to silica gel column chromatography (eluent: cyclohexane: ethyl acetate: 10:1) and recrystallization (solvent: toluene) to obtain compound 149 (purity ≧ 99.3% by HPLC, 20.48g, yield 68%).

Mass spectrum m/z: 754.27 (calculated value: 752.26). Theoretical element content (%) C₅₁H₃₆N₄And OS: c, 81.36; h, 4.82; n, 7.44; o, 2.12; and S, 4.26. Measured elemental content (%): c, 80.79; h, 4.98; n, 7.63; o, 3.37; and S, 3.23.¹H NMR(600MHz,CDCl₃) (δ, ppm): 8.43(dd,1H),8.03(dd,1H),7.99(dd,2H),7.85(d,1H),7.73(q,1H),7.55(td,1H),7.51(dd,1H),7.44(td,1H),7.36-7.31(m,3H), 7.24-7.23 (m,6H),7.18(d,2H),7.08(dd,2H), 7.01-6.99 (m,3H),6.86(dd,1H), 6.75-6.73 (m,2H),6.64(dd,1H),6.60(d,1H),5.41(s,2H),4.61(d, 4H). The above results confirmed that the obtained product was the objective product.

EXAMPLE 8 Synthesis of Compound 159

Synthesis of intermediates a to 159:

intermediate a-159 was synthesized by the method for synthesizing intermediate a-1 by replacing raw material j-1 in example 1 with equimolar raw material j-159 (purity of solid by HPLC ≧ 99.0%, 23.95g, yield 63%).

Mass spectrum m/z: 378.94 (calculated value: 379.93). Theoretical element content (%) C₁₅H₁₂Br₂N₂: c, 47.40; h, 3.18; br, 42.05; n, 7.37. Measured elemental content (%): c, 47.37; h, 3.18; br, 42.06; and N, 7.39. The above results confirmed that the obtained product was the objective intermediate.

Synthesis of compound 159:

the intermediate a-1 in example 1 was replaced with an equimolar amount of the intermediate a-159, and the synthesis method of compound 1 was followed to obtain compound 159 (purity by HPLC ≧ 99.4%, 10.46g, yield 71%).

Mass spectrum m/z: 737.29 (calculated value: 736.28). Theoretical element content (%) C₅₁H₃₆N₄O₂: c, 83.13; h, 4.92; n, 7.60; and O, 4.34. Measured elemental content (%): c, 83.24; h, 4.78; n, 7.71; and O, 4.26.¹H NMR(600MHz,CDCl₃) (δ, ppm): 7.99(dd,2H),7.61(s,2H),7.54(dd,2H), 7.45-7.43 (m,4H),7.35(td,2H), 7.25-7.22 (m,8H),7.16(td,2H),7.00(p,2H), 6.84-6.79 (m,3H),6.73(dd,2H),6.59(dd,1H),5.41(s,2H),4.61(d, 4H). The above results confirmed that the obtained product was the objective product.

EXAMPLE 9 Synthesis of Compound 163

Synthesis of intermediates a-163:

to a 500ml three-necked flask was added 200ml of TFA at-15 ℃ and j-1(8.60g, 50mmol), j-163(8.60g, 50mmol), (CH) were added successively under vigorous stirring₂O)_n(6.12g, 204mmol), the mixed solution was stirred for 20min to room temperature and stirring was continued for 48 h. Ice and excess NH were added slowly at 0 deg.C₃(25% aqueous solution) to the mixture, stirring, over CH₂Cl₂Extraction, MgSO₄After drying, the mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent cyclohexane: ethyl acetate: 10:1) to obtain intermediate a-163 (purity of solid by HPLC ≧ 99.0%, 7.41g, yield 39%).

Mass spectrum m/z: 380.94 (calculated value: 379.93). Theoretical element content (%) C₁₅H₁₂Br₂N₂: c, 47.40; h, 3.18; br, 42.05; n, 7.37. Measured elemental content (%): c, 47.35; h, 3.20; br, 42.05; and N, 7.40. The above results confirmed that the obtained product was the objective intermediate.

Synthesis of compound 163:

the intermediate a-1 in example 1 was replaced with an equal mole of the intermediate a-163, and the raw material k-1 was replaced with an equal mole of the raw material h-163, to obtain compound 163 according to the synthesis method of compound 1 (purity of solid by HPLC ≧ 99.6%, 12.53g, yield 68%).

Mass spectrum m/z: 921.30 (calculated value: 920.30). Theoretical element content (%) C₆₃H₄₄N₄S₂: c, 82.14; h, 4.81; n, 6.08; and S, 6.96. Measured elemental content (%): c, 82.35; h, 4.73; n, 6.06; and S, 6.85.¹H NMR(600MHz,CDCl₃) (δ, ppm): 9.67(d,1H),8.42(dd,1H),8.27(dd,1H),8.23(d,1H),8.16(dd,1H), 8.02-7.97 (m,3H),7.88(dd,1H), 7.82-7.78 (m,2H), 7.54-7.47 (m,6H),7.31(td,3H),7.24(td,6H),7.11-7.07(m,5H),7.00(tt,2H),6.79(d,1H),6.76(dd,1H),6.66(dd,1H),6.54(q,1H),6.15(d,1H),5.41(s,2H),4.61(d, 4H). The above results confirmed that the obtained product was the objective product.

EXAMPLE 10 Synthesis of Compound 167

Synthesis of intermediate a-167:

the intermediate a-167 was obtained according to the method for synthesizing the intermediate a-1 by replacing the raw material j-1 in example 1 with an equimolar amount of the raw material j-167 (purity ≧ 97.8% by HPLC, 11.22g, yield 55%).

Mass spectrum m/z: 409.96 (calculated value: 407.97). Theoretical element content (%) C₁₇H₁₆Br₂N₂: c, 50.03; h, 3.95; br, 39.16; and N, 6.86. Measured elemental content (%): c, 50.01; h, 3.97; br, 39.17; and N, 6.85. The above results confirmed that the obtained product was the objective intermediate.

Synthesis of compound 167:

the intermediate a-1 in example 1 was replaced with an equal mole of the intermediate a-167, and the intermediate k-1 was replaced with an equal mole of the intermediate k-17, and the synthesis method of the compound 1 was followed to obtain the compound 167 (purity of solid by HPLC ≧ 99.1%, 11.32g, yield 71%).

Mass spectrum m/z: 797.27 (calculated value: 796.27). Theoretical element content (%) C₅₃H₄₀N₄ S₂: c, 79.87; h, 5.06; n, 7.03; and S, 8.04. Measured elemental content (%): c, 79.81; h, 5.09; n, 7.08; and S, 8.02.¹H NMR(600MHz,CDCl₃) (δ, ppm): 8.45(dd,2H), 8.05-8.01 (m,4H),7.92(d,1H),7.83(d,1H), 7.58-7.54 (m,2H),7.31(td,2H), 7.25-7.19 (m,10H),7.02-6.99(m,2H),6.95(d,1H),6.74(s,1H),6.72(s,1H),6.66(d,1H),5.41(s,2H),4.61(d,4H),2.21(d, 6H). The above results confirmed that the obtained product was the objective product.

Comparative example 1 device preparation example:

comparative example 1: the ITO glass substrate as the anode is ultrasonically washed using a solvent such as pure water, isopropyl alcohol, acetone, methanol, etc., and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes, and the cleaned glass substrate is placed in a vacuum deposition apparatus.

2-TNATA was vacuum deposited on an ITO glass substrate to form a hole injection layer of 60nm thickness, and NPB was vacuum deposited on the hole injection layer to form a hole transport layer of 30nm thickness. Co-depositing CBP (Green phosphorescent host) and Ir (ppy) on the hole transport layer at a weight ratio of 95:5₃(green phosphorescent dopant) to form a light-emitting layer having a thickness of 30 nm. TPBi was then deposited on the light-emitting layer to form an electron transport layer of 30nm thickness. Depositing LiF on the electron transport layer to form an electron injection layer with a thickness of 1nm, and depositing Al on the electron injection layer in vacuum to formA cathode of 300nm thickness, thereby forming a LiF/Al electrode.

Comparative examples 2 to 4 device preparation examples:

organic light-emitting devices of comparative examples 2 to 4 were fabricated in substantially the same manner as in comparative example 1, except that the compounds HTM-1, HTM-2, HTM-3 were each used as a material for forming a hole transport layer.

Application examples 1 to 10 device production examples (for use as hole transport layers):

organic light-emitting devices of application examples 1 to 10 were manufactured in substantially the same manner as in comparative example 1, except that compounds 1, 17, 38, 56, 81, 107, 149, 159, 163, 167 were each used as a material for forming a hole transport layer.

The test software, the computer, the K2400 digital source manufactured by Keithley corporation, usa, and the PR788 spectral scanning luminance meter manufactured by Photo Research corporation, usa were combined into a joint IVL test system to test the efficiency, current density, and driving voltage of the organic light emitting device. The environment of the test is atmospheric environment, and the temperature is room temperature.

Table 1 shows the results of the test of the light emitting characteristics of the light emitting devices prepared by the compounds prepared in the examples of the present invention and the comparative materials.

Table 1 test of light emitting characteristics of light emitting device

As shown in table 1, compared with comparative examples 1 to 4, the devices using the arylamine compound of the present invention as the hole transport layer material have lower driving voltage and the light emitting efficiency of the devices is significantly improved.

Compared with comparative examples 1-4, the arylamine compound provided by the invention has the advantages that a three-dimensional inverted V-shaped kink structure is introduced into a molecule conjugated system, so that pi-pi dense packing is not facilitated to be formed during molecule packing, the aggregation state fluorescence quenching phenomenon caused by the pi-pi dense packing can be effectively improved, and then at least one dibenzothiophene/dibenzofuran/carbazole or fluorene substituted amine group is introduced, so that the hole transmission performance can be enhanced, the hole mobility can be improved, and the roll-off phenomenon can be inhibited.

It should be understood that the present invention has been particularly described with reference to particular embodiments thereof, but that various changes in form and details may be made therein by those skilled in the art without departing from the principles of the invention and, therefore, within the scope of the invention.

Claims

1. An arylamine compound is characterized in that the structure of the arylamine compound is any one of the following structures:

wherein, in chemical formulas 1-1 to 1-3,

Ar₁one selected from the structures shown below:

wherein L is_aOne selected from single bond, phenylene, tolylene and biphenylene;

R₁selected from phenyl, tolyl, biphenylOne of naphthyl; r₂、R₃Independently selected from hydrogen, methyl, ethyl, phenyl;

y is selected from an integer of 0 to 3;

Ar₂～Ar₄independently selected from any one of the structures shown below:

R₅one selected from hydrogen, deuterium, methyl, ethyl, phenyl, tolyl, pentadeuterated phenyl and biphenyl;

R₆one selected from phenyl, tolyl, biphenyl and naphthyl;

L₁、L₂independently selected from one of single bond, phenylene and tolylene;

R_a、R_bindependently selected from one of hydrogen, deuterium, alkyl of C1-C10 and aryl of C6-C12;

m is an integer from 0 to 3; n is an integer from 0 to 3.

2. An arylamine compound is characterized in that the structure of the arylamine compound is any one of the following structures:

wherein, in chemical formulas 1-1 to 1-3,

Ar₁one selected from the structures shown below:

R₁one selected from phenyl, tolyl, biphenyl and naphthyl; r₂、R₃Independently selected from hydrogen, methyl, ethyl, phenyl; r₄One selected from hydrogen, deuterium, methyl, ethyl, phenyl, tolyl, pentadeuterated phenyl and biphenyl;

y is selected from an integer of 0 to 3;

Ar₂～Ar₄independently selected from any one of the structures shown below:

m is an integer from 0 to 3; n is an integer from 0 to 3.

3. An arylamine compound according to claim 1 or 2 wherein R is_a、R_bIndependently selected from one of hydrogen, methyl, ethyl, isopropyl, tertiary butyl, phenyl, biphenyl and naphthyl.

4. An arylamine compound is characterized in that the arylamine compound is selected from any one of the following structures:

5. an organic light-emitting device comprising a cathode, an anode, and one or more organic layers disposed between or outside the cathode and anode; the organic layer comprises at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a covering layer; the organic layer contains any one or a combination of at least two of the arylamine compounds described in any one of claims 1 to 4.

6. An organic light-emitting device according to claim 5, wherein the organic layer comprises a hole transport layer containing any one or a combination of at least two of the arylamine compounds according to any one of claims 1 to 4.