Triarylamine compound and organic electroluminescent device

Abstract

The invention relates to the field of organic light-emitting diode preparation, in particular to a triarylamine compound and an organic light-emitting device. Wherein the triarylamine compound has a structure as shown in a formula (a): # imgabs0 #, and the device adopting the compound provided by the invention has long service life and high efficiency.

Description

Technical Field

[0001] The invention relates to the field of organic light emitting diode preparation, in particular to a triarylamine compound and an organic electroluminescent device. Background Art

[0002] OLED, or organic light-emitting diode, has the advantages of high brightness, high contrast, and the ability to design transparent displays, while also having low production costs.

[0003] The working principle of OLED devices is as follows: when voltage is applied to an organic electroluminescent device, holes and electrons are injected from the anode and cathode respectively, and recombine in the light-emitting layer to form excitons. When the excitons thus formed recover from an unstable excited state with higher energy to a stable ground state with lower energy, energy is released in the form of photons, and the device emits light. The materials of the auxiliary layers of OLED devices also have a very important influence on the efficiency and life of the device.

[0004] In the prior art, the main purpose of adding an electron blocking layer is, on the one hand, to block the uncombined electrons in the light-emitting layer and transfer holes to the light-emitting layer, and on the other hand, to adjust the optical microcavity of the device by designing the thickness of this layer. These two aspects mainly improve the luminous efficiency of the device. However, the electron blocking layer is also attacked by high-energy excitons in the light-emitting layer. Therefore, in order to obtain an OLED device with a long service life, the electron blocking layer material needs to have a strong ability to resist excitons.

[0005] Triarylamine compounds, which have good hole transport properties and electron blocking characteristics, are widely used in auxiliary layers, such as hole transport layers or electron blocking layers. However, the service life and efficiency of the device still need to be further improved. Summary of the invention

[0006] In view of the above-mentioned shortcomings of the prior art, the object of the present invention is to provide a triarylamine compound and an organic electroluminescent device. The device using the compound provided by the present invention has a high service life and efficiency.

[0007] The present invention provides a triarylamine compound, wherein the triarylamine compound has a structure as shown in formula (a):

[0008]

[0009] in,

[0010] R 1 To R 8 are the same as or different from each other, and are each independently selected from H or D;

[0011] L,L 1 ,L 2are the same as or different from each other, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms;

[0012] Ar 1 ,Ar 2 are the same as or different from each other and are independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms;

[0013] Each occurrence of R is independently selected from deuterium, cyano, nitro, halogen, trifluoromethyl, deuterated methyl, straight or branched chain alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkenyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, carbonyl having 1 to 10 carbon atoms, silyl having 3 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms;

[0014] n represents the number of R, selected from an integer between 0 and 7;

[0015] Any hydrogen in formula (a) may optionally be replaced by deuterium.

[0016] The present invention further provides a functional layer, which comprises the aforementioned triarylamine compound of the present invention.

[0017] The present invention also provides use of the aforementioned triarylamine compound of the present invention and / or the aforementioned functional layer of the present invention in an organic electroluminescent device.

[0018] The present invention also provides an organic electroluminescent device, which comprises a first electrode, a second electrode and a functional layer as described above in the present invention, wherein the functional layer is at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron injection layer or an electron transport layer.

[0019] The present invention also provides a display or lighting device, which comprises the organic electroluminescent device as described above in the present invention.

[0020] By adopting the above technical solution, the beneficial effects of the present invention are:

[0021] The present invention provides a triarylamine compound based on 2',3',5',6'-tetrahydrospiro[fluorene-9,4'-pyran], which is used in the hole transport layer or electron blocking layer of blue light, red light and green light organic electroluminescent devices. Compared with the corresponding comparative example compounds, various performance indicators of the device (such as operating voltage, current efficiency and life span) are improved to varying degrees.

[0022] The present invention provides each embodiment compound, it is characterised in that tetrahydropyran is introduced to replace at the 9-position of fluorenyl to form a spirocyclic structure. On the one hand, the spirocyclic structure has a strong steric hindrance effect, which is conducive to the promotion of the triplet energy level of the molecule, and is also conducive to the formation of a continuous and uniform amorphous film in the macroscopic state of the molecule, and maintains a stable film morphology when the device works for a long time to generate a large amount of Joule heat, that is, it is conducive to the stability improvement of the device. On the other hand, the oxygen atom in the tetrahydropyran fragment has both the inductive effect of electron withdrawal and the hyperconjugation effect of electron donation, and this fragment is introduced into the fluorenyl, which can further enhance the electron donation and stability of the fluorenyl, and correspondingly, the present invention comprising this fluorenyl provides each embodiment compound, with a strong hole transport ability and molecular stability, so as to be conducive to the device operating voltage reduction, current efficiency and lifespan improvement. Thirdly, by adjusting the different substituents connected to the aromatic amine group and / or the fluorene group, the frontier orbital energy level and triplet energy level of the molecule can be effectively regulated, making it selectively adaptable to the hole transport layer material or electron blocking layer material of a variety of color organic electroluminescent devices. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Figure 1 Schematic diagram of the structure of an organic electroluminescent device in a blue light device embodiment.

[0024] Figure 2 Schematic diagram of the structure of the organic electroluminescent device in the green light device and the red light device embodiments.

[0025] In the figure:

[0026] 101 Base

[0027] 102 first electrode

[0028] 103 Hole injection layer

[0029] 104 Hole transport layer

[0030] 105 Electron blocking layer

[0031] 106 Luminescent Layer

[0032] 107 Hole blocking layer

[0033] 108 Electron transport layer

[0034] 109 second electrode

[0035] 110 Covering DETAILED DESCRIPTION

[0036] Hereinafter, the embodiments of the triarylamine compound and the organic electroluminescent device provided by the present invention will be described in detail.

[0037] The inventors of the present proposal surprisingly found that compounds with a specific structure, when used in the hole transport layer or electron blocking layer of blue, red and green organic electroluminescent devices, have different degrees of improvement in various performance indicators of the devices (such as operating voltage, current efficiency and life span, etc.) compared with the corresponding comparative example compounds, thereby completing the present invention.

[0038] Hereinafter, the present application will be described in detail. However, the following description is intended to explain the present invention and is not intended to limit the scope of the present invention in any way.

[0039] In the present application, the term "straight or branched alkyl group having 1 to 10 carbon atoms" used alone or in combination means a straight or branched alkyl group having 1 to 10 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 10, 1 to 8, the number of carbon atoms is further preferably 1 to 6, and more preferably 1 to 4. The above-mentioned alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, and the like.

[0040] In the present application, the term "cycloalkyl having 3 to 10 carbon atoms" used alone or in combination means a mono- or polycyclic hydrocarbon having 3 to 10 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably 3 to 8, and the number of carbon atoms is preferably 3 to 6. The above-mentioned cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, adamantyl, and the like.

[0041] In the present application, the term "alkenyl" used alone or in combination includes straight or branched alkenyl groups, the number of carbon atoms of which can be, for example, 2 to 10, 2 to 8, etc. By way of example, alkenyl groups include, but are not limited to, vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. In the present disclosure, the "alkenyl group" is an optionally substituted alkenyl group.

[0042] In the present application, the term "alkoxy", used alone or in combination, refers to -O(alkyl). Optionally, the alkyl portion of the alkoxy group may contain 1-10 carbon atoms, 1-8 carbon atoms, 1-7 carbon atoms, 1-6 carbon atoms, 1-5 carbon atoms, or 1-4 carbon atoms, etc. Alkoxy groups, for example, may include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, etc.

[0043] In the present application, the term "alkylthio" used alone or in combination refers to -S(alkyl). Optionally, the alkyl portion of the alkylthio group may contain 1-10 carbon atoms, 1-8 carbon atoms, 1-7 carbon atoms, 1-6 carbon atoms, 1-5 carbon atoms or 1-4 carbon atoms, etc. Alkylthio groups, for example, may include but are not limited to methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, etc.

[0044] In the present application, the term "silyl" used alone or in combination includes, for example, silyl, disilyl, etc. In the present application, silyl is represented by the formula Indicates that A 1 , A 2 and A 3 and R and R are independently hydrogen or substituted or unsubstituted alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl as described herein. wait.

[0046] In the present application, the term "aryl" used alone or in combination means a monocyclic or condensed ring group derived from an aromatic hydrocarbon having a ring backbone carbon atom, wherein the number of the ring backbone carbon atoms is preferably 6 to 22, 6 to 18, 6 to 15, more preferably 6 to 12, and may be partially saturated and may contain a spiro structure. Examples of aryl groups specifically include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthryl, triphenylenyl, phenylphenanthryl, anthracenyl, benzanthryl, indenyl, triphenylene, pyrenyl, naphthacene, peryl, mesityl, benzo, naphthacene, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluorene-fluorenyl]yl, spiro[fluorene-benzofluorenyl]yl, azulenyl, tetramethyl-dihydrophenanthryl and the like. More specifically, the aryl group can be o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumyl, m-cumyl, p-cumyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl ...4-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, m-terphenyl-4-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, m-terphenyl-4-yl, m-terphenyl-4-yl, m-terphenyl-4-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, m-terphenyl-4-yl, m-ter biphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-dimethyl- Phenyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1-yl, 2-yl, 3-yl, 4-yl, 5-yl, 6-yl, benzo[c]phenanthrenyl, benzo[g]yl, 1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-12-benzo[a]fluorenyl, 11,11-dimethyl-13-benzo[a]fluorenyl, 11,11-dimethyl-14-benzo[a]fluorenyl, 11,11-dimethyl-15-benzo[a]fluorenyl, 11,11-dimethyl-16-benzo[a]fluorenyl, 11,11-dimethyl-17-benzo[a]fluorenyl, 11,11-dimethyl-18-benzo[a]fluorenyl, 11,11-dimethyl-19-benzo[a]fluorenyl, 11,11-dimethyl-111-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11- dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl -benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[ b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-11-Diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthryl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthryl, etc.

[0047] In the present application, the term "heteroaryl" used alone or in combination is an aryl group having a ring skeleton atom, wherein the ring skeleton atom includes at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, Se and Ge, preferably at least one heteroatom selected from N, O and S, wherein the number of ring skeleton carbon atoms is preferably 3 to 30, 3 to 22, 3 to 20, 3 to 15, 3 to 12, etc. The number of heteroatoms in the heteroaryl group is preferably 1 to 4. The above-mentioned heteroaryl group may be a monocyclic ring or a condensed ring condensed with at least one benzene ring; and may be partially saturated. In addition, herein, the above-mentioned heteroaryl group may be a heteroaryl group formed by connecting at least one heteroaryl group or aryl group to the heteroaryl group via one or more single bonds. Examples of heteroaryl groups include monocyclic heteroaryl groups, including furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and the like, and fused ring heteroaryl groups, including benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, thiophene, dibenzothiophene, dibenzoselenophene, benzofuranoquinolyl, benzofuranoquinazolinyl, benzofurano naphthyridinyl, benzofuranopyrimidinyl, naphthyridinyl, benzothiophenoquinolyl, benzothiophenoquinazolinyl, benzothiophenonaphthyridinyl, benzothiophenopyrimidinyl, naphthyridinyl, pyrimidoindolyl, benzopyrimidoindolyl, benzofuranopyrazinyl, naphthyridinyl, pyrazinyl, benzothienopyrazinyl, naphthienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl The heteroaryl group may be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 6-pyrimidyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-indolizidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl yl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2- benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl-1 -yl, azacarbazole-2-yl, azacarbazole-3-yl, azacarbazole-4-yl, azacarbazole-5-yl, azacarbazole-6-yl, azacarbazole-7-yl, azacarbazole-8-yl, azacarbazole-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridin ... 0-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol -5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl , 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2, 3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophene, 2-naphtho-[1,2-b]-benzothiophene, 3-naphtho-[1,2-b]-benzothiophene 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1 ,2-b]-benzothiophene, 1-naphtho-[2,3-b]-benzothiophene, 2-naphtho-[2,3-b]-benzothiophene, 3-naphtho-[2,3-b]-benzothiophene, 4-naphtho-[2,3-b]-benzothiophene, 5-naphtho-[2,3-b]-benzothiophene, 1-naphtho-[2,1-b]-benzothiophene 1-b-benzothiophene, 2-naphtho-[2,1-b]-benzothiophene, 3-naphtho-[2,1-b]-benzothiophene, 4-naphtho-[2,1-b]-benzothiophene, 5-naphtho-[2,1-b]-benzothiophene, 6-naphtho-[2,1-b]-benzothiophene, 7-naphtho-[2,1-b]-benzothiophene, 8-naphtho-[2,1-b]-benzothiophene,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzofurano[3,2-d]pyrimidinyl, 6-benzofurano[3,2-d]pyrimidinyl, 7-benzofurano[3,2-d]pyrimidinyl, 8-benzofurano[3,2-d]pyrimidinyl, 9-benzofurano[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl, 6-benzothio[3,2-d]pyrimidinyl, 7-benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9-benzothio[3,2-d]pyrimidinyl, 2-benzofurano[3,2-d]pyrimidinyl, , 6-benzofurano[3,2-d]pyrazinyl, 7-benzofurano[3,2-d]pyrazinyl, 8-benzofurano[3,2-d]pyrazinyl, 9-benzofurano[3,2-d]pyrazinyl, 2-benzothio[3,2-d]pyrazinyl, 6-benzothio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl oxazine, 8-benzothio[3,2-d]pyrazine, 9-benzothio[3,2-d]pyrazine, 1-silicon fluorenyl, 2-silicon fluorenyl, 3-silicon fluorenyl, 4-silicon fluorenyl, 1-germanium fluorenyl, 2-germanium fluorenyl, 3-germanium fluorenyl, 4-germanium fluorenyl, 1-dibenzoselenophene, 2-dibenzoselenophene, 3-dibenzoselenophene, 4-dibenzoselenophene, etc.

[0048] In addition, the term "substituted" in the expression "substituted or unsubstituted" means that the hydrogen atom in a functional group is replaced by another atom or functional group (i.e., a substituent). Preferably, in the present application, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, etc. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, adamantyl, phenyl, naphthyl, phenanthrenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl; optionally, any hydrogen atom in the aforementioned substituent can be replaced by deuterium. For example, the substituted substituents may be, for example, deuterium, cyano, halogen groups, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothiophenyl, dibenzofuranyl, etc.

[0049] In the present application, the term "halogen group" includes F, Cl, Br and I.

[0050] Hereinafter, the triarylamine compound of the present invention will be described.

[0051] The present invention provides a triarylamine compound having a structure as shown in formula (a):

[0052]

[0053] In the present invention, any hydrogen in the formula (a) may be optionally replaced by deuterium.

[0054] In the present invention, R 1 To R 8 are the same as or different from each other, and are each independently selected from H or D.

[0055] In the present invention, L, L 1 ,L 2 The same as or different from each other, each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms. The "substituted" means that any hydrogen atom in any of the above groups is replaced by a substituent. Specifically, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl group having 1 to 6 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, and heteroaryl group having 3 to 20 carbon atoms; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For more example, the substituted substituent can be deuterium, cyano, halogen group, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl, etc.

[0056] In some embodiments of the present invention, L, L 1 ,L 2The same as or different from each other, each independently selected from a single bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms. The "substituted" means that any hydrogen atom in any of the above groups is replaced by a substituent. Specifically, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl group having 1 to 6 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, and heteroaryl group having 3 to 20 carbon atoms; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For more example, the substituted substituent can be deuterium, cyano, halogen group, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl, etc.

[0057] In some embodiments of the present invention, L, L 1 ,L 2 The same as or different from each other, each independently selected from a single bond, an arylene group having 6 to 18 carbon atoms, or a heteroarylene group having 3 to 18 carbon atoms. The "substituted" means that any hydrogen atom in any of the above groups is replaced by a substituent. Specifically, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl group having 1 to 6 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, and heteroaryl group having 3 to 20 carbon atoms; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For more example, the substituted substituent can be deuterium, cyano, halogen group, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl, etc.

[0058] In some embodiments of the present invention, L, L1 ,L 2 The same as or different from each other, each independently selected from a single bond, an arylene group having 6 to 16 carbon atoms, or a heteroarylene group having 3 to 16 carbon atoms. The "substituted" means that any hydrogen atom in any of the above groups is replaced by a substituent. Specifically, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl group having 1 to 6 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, and heteroaryl group having 3 to 20 carbon atoms; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For more example, the substituted substituent can be deuterium, cyano, halogen group, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl, etc.

[0059] In some embodiments of the present invention, L 0 ,L 1 ,L 2 The same as or different from each other, each independently selected from a single bond, an arylene group having 6 to 12 carbon atoms, or a heteroarylene group having 3 to 12 carbon atoms. The "substituted" means that any hydrogen atom in any of the above groups is replaced by a substituent. Specifically, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl group having 1 to 6 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, and heteroaryl group having 3 to 20 carbon atoms; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For more example, the substituted substituent can be deuterium, cyano, halogen group, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl, etc.

[0060] In some embodiments of the present invention, L, L 1 , L 2 Each is independently selected from the following groups which are single-bonded, substituted or unsubstituted: phenylene, biphenylene, naphthylene, phenanthrenyl, fluorenylene, dibenzothienylene, dibenzofuranylene. The "substituted" means that any hydrogen atom in any of the above groups is replaced by a substituent. Specifically, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, and heteroaryl with 3 to 20 carbon atoms; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For more example, the substituted substituent can be deuterium, cyano, halogen group, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl, etc.

[0061] In the present invention, Ar 1 ,Ar 2The same as or different from each other, each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. The "substituted" means that any hydrogen atom in any of the above groups is replaced by a substituent. Specifically, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl group having 1 to 6 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, and heteroaryl group having 3 to 20 carbon atoms; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For more example, the substituted substituent can be deuterium, cyano, halogen group, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl, etc.

[0062] In some embodiments of the present invention, Ar 1 ,Ar 2 Each is independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 25 carbon atoms. The "substituted" means that any hydrogen atom in any of the above groups is replaced by a substituent. Specifically, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl group having 1 to 6 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, and heteroaryl group having 3 to 20 carbon atoms; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For more example, the substituted substituent can be deuterium, cyano, halogen group, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl, etc.

[0063] In some embodiments of the present invention, Ar 1 ,Ar 2 Each is independently selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms. The "substituted" means that any hydrogen atom in any of the above groups is replaced by a substituent. Specifically, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl group having 1 to 6 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, and heteroaryl group having 3 to 20 carbon atoms; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For more example, the substituted substituent can be deuterium, cyano, halogen group, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl, etc.

[0064] In some embodiments of the present invention, Ar 1 ,Ar 2Each is independently selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms. The "substituted" means that any hydrogen atom in any of the above groups is replaced by a substituent. Specifically, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl group having 1 to 6 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, and heteroaryl group having 3 to 20 carbon atoms; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For more example, the substituted substituent can be deuterium, cyano, halogen group, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl, etc.

[0065] In some embodiments of the present invention, Ar 1 ,Ar 2 Each is independently selected from a substituted or unsubstituted aryl group having 6 to 16 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 16 carbon atoms. The "substituted" means that any hydrogen atom in any of the above groups is replaced by a substituent. Specifically, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl group having 1 to 6 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, and heteroaryl group having 3 to 20 carbon atoms; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For more example, the substituted substituent can be deuterium, cyano, halogen group, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl, etc.

[0066] In some embodiments of the present invention, Ar1 ,Ar 2 Each is independently selected from a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms. The "substituted" means that any hydrogen atom in any of the above groups is replaced by a substituent. Specifically, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl group having 1 to 6 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms, and heteroaryl group having 3 to 20 carbon atoms; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For more example, the substituted substituent can be deuterium, cyano, halogen group, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl, etc.

[0067] In some embodiments of the present invention, Ar 1 ,Ar 2Each is independently selected from the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, diphenylfluorenyl, spirofluorenyl, spirofluorenyl, carbazolyl, dibenzothiophenyl, dibenzofuranyl, benzofluorenyl, benzospirofluorenyl, benzocarbazolyl, benzonaphthothiophenyl, benzonaphthofuranyl. Wherein, the "substituted" means that any hydrogen atom in any of the above groups is replaced by a substituent. Specifically, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, and heteroaryl with 3 to 20 carbon atoms; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For more example, the substituted substituent can be deuterium, cyano, halogen group, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl, etc.

[0068] In the present invention, each occurrence of R is independently selected from deuterium, cyano, nitro, halogen, trifluoromethyl, deuterated methyl, straight or branched alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkenyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, carbonyl having 1 to 10 carbon atoms, silane having 3 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms.

[0069] In some embodiments of the invention, each occurrence of R is independently selected from deuterium.

[0070] In some embodiments of the present invention, each occurrence of R is independently selected from cyano.

[0071] In some embodiments of the invention, each occurrence of R is independently selected from nitro.

[0072] In some embodiments of the present invention, each occurrence of R is independently selected from a halogen group.

[0073] In some embodiments of the present invention, each occurrence of R is independently selected from trifluoromethyl.

[0074] In some embodiments of the invention, each occurrence of R is independently selected from deuterated methyl.

[0075] In some embodiments of the present invention, each occurrence of R is independently selected from a straight chain or branched chain alkyl group having 1 to 10 carbon atoms. It can be selected from a straight chain or branched chain alkyl group having 1 to 8 carbon atoms, a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, or a straight chain or branched chain alkyl group having 1 to 4 carbon atoms. For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, etc.

[0076] In some embodiments of the present invention, each occurrence of R is independently selected from a cycloalkyl group having 3 to 10 carbon atoms, and may be a cycloalkyl group having 3 to 8 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, adamantyl, and the like.

[0077] In some embodiments of the present invention, each occurrence of R is independently selected from alkenyl groups having carbon atoms of 1 to 10. It can be alkenyl groups having carbon atoms of 1 to 8, alkenyl groups having carbon atoms of 1 to 6, and alkenyl groups having carbon atoms of 1 to 4. For example, vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.

[0078] In some embodiments of the present invention, each occurrence of R is independently selected from an alkoxy group having 1 to 10 carbon atoms, which may be an alkoxy group having 1 to 8 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, etc.

[0079] In some embodiments of the present invention, each occurrence of R is independently selected from an alkylthio group having 1 to 10 carbon atoms, and may be an alkylthio group having 1 to 8 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, or an alkylthio group having 1 to 4 carbon atoms, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, and the like.

[0080] In some embodiments of the present invention, each occurrence of R is independently selected from a carbonyl group having 1 to 10 carbon atoms, and may be selected from a carbonyl group having 1 to 8 carbon atoms, a carbonyl group having 1 to 6 carbon atoms, or a carbonyl group having 1 to 4 carbon atoms.

[0081] In some embodiments of the present invention, each occurrence of R is independently selected from a silane group having 3 to 10 carbon atoms. It can be selected from a silane group having 3 to 8 carbon atoms, a silane group having 3 to 6 carbon atoms, or a silane group having 3 to 4 carbon atoms. For example wait.

[0082] In some embodiments of the present invention, each occurrence of R is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. It can be selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 16 carbon atoms; a substituted or unsubstituted heteroaryl group having 3 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 16 carbon atoms. For another example, it can be selected from the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl. Among them, the "substituted" means that any hydrogen atom in any of the above groups is replaced by a substituent. Specifically, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, and heteroaryl with 3 to 20 carbon atoms; optionally, any hydrogen atom in the above substituent can be replaced by deuterium. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, and dibenzofuranyl; optionally, any hydrogen atom in the above substituent can be replaced by deuterium. For example, the substituted substituents may be, for example, deuterium, cyano, halogen groups, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothiophenyl, dibenzofuranyl, etc.

[0083] In some embodiments of the present invention, n represents the number of R, which is selected from an integer between 0 and 7. For example, n is 0, 1, 2, 3, 4, 5, 6, or 7.

[0084] In the present invention, optionally, the triarylamine compound is selected from any one of formula (a1) or (a2):

[0085]

[0086] Among them, Ar 1 ,Ar 2 ,L,L 1 ,L 2 ,R,n has the same meaning as in formula (a).

[0087] In the present invention, optionally, the triarylamine compound is selected from any one of the following structures:

[0088]

[0089] Among them, R 1 To R 8 ,Ar 1 ,Ar 2 ,L,L 1 ,L 2 ,R,n has the same meaning as in formula (a).

[0090] In the present invention, optionally, the triarylamine compound is selected from any one of the following structures:

[0091]

[0092]

[0093] Among them, R 1 To R 8 ,Ar 1 ,Ar 2 ,L,L 1 ,L 2 The meaning represented is the same as formula (a).

[0094] R a is selected from deuterium, cyano, fluorine, trifluoromethyl, deuterated methyl, a straight-chain or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an adamantyl group, or a substituted or unsubstituted group of the following: phenyl, biphenyl, naphthyl, phenanthryl, fluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl.

[0095] Optionally, R a Selected from deuterium.

[0096] Optionally, R aSelected from cyano.

[0097] Optionally, R a Selected from fluorine.

[0098] Optionally, R a Selected from trifluoromethyl.

[0099] Optionally, R a Selected from deuterated methyl.

[0100] Optionally, R a It is selected from a straight chain or branched chain alkyl group having 1 to 6 carbon atoms. It can be selected from a straight chain or branched chain alkyl group having 1 to 4 carbon atoms. For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, etc.

[0101] Optionally, R a The carbon number is selected from cycloalkyl and adamantyl groups having carbon atoms of 3 to 6. It can be selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, adamantyl and the like.

[0102] Optionally, R a Selected from the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl. Wherein, the "substituted" means that any hydrogen atom in any of the above groups is replaced by a substituent. Specifically, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For more example, the substituted substituent can be deuterium, cyano, halogen group, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl, etc.

[0103] R bA straight-chain or branched alkyl group having 1 to 6 carbon atoms, a deuterated methyl group, a cycloalkyl group having 3 to 6 carbon atoms, an adamantyl group, or a substituted or unsubstituted group as follows: a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group.

[0104] Optionally, R b It is selected from a straight chain or branched chain alkyl group having 1 to 6 carbon atoms. It can be selected from a straight chain or branched chain alkyl group having 1 to 4 carbon atoms. For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, etc.

[0105] Optionally, R b Selected from deuterated methyl.

[0106] Optionally, R b The carbon number is selected from cycloalkyl and adamantyl groups having carbon atoms of 3 to 6. It can be selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, adamantyl and the like.

[0107] Optionally, R b Selected from the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl. Wherein, the "substituted" means that any hydrogen atom in any of the above groups is replaced by a substituent. Specifically, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl; optionally, any hydrogen atom in the above substituents can be replaced by deuterium. For more example, the substituted substituent can be deuterium, cyano, halogen group, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl, etc.

[0108] n is selected from an integer between 0 and 7. For example, n is 0, 1, 2, 3, 4, 5, 6, 7.

[0109] m is selected from an integer between 0 and 6. For example, n is 0, 1, 2, 3, 4, 5, 6.

[0110] In some preferred embodiments of the present invention, the compound represented by formula (a) is selected from any one of the following chemical structures:

[0111]

[0112]

[0113]

[0114] Hereinafter, a functional layer to which the triarylamine compound is applied, and an organic electroluminescent device, a display or a lighting device including the functional layer will be described.

[0115] The present application also provides an organic electroluminescent device, comprising a first electrode, a second electrode and the aforementioned organic layer. As an example, the first electrode is an anode, the second electrode is a cathode, and the cathode can be one or more layers. The organic layer is located between the first electrode and the second electrode. The organic layer can be a single-layer structure or a multilayer tandem structure in which two or more organic layers are laminated. The organic layer includes at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer and an electron transport layer. In some preferred embodiments, the triarylamine compound of the present application is used as an electron blocking layer material, a hole transport layer material or a light-emitting layer main material.

[0116] In some specific embodiments, the structure of the organic electroluminescent device can be selected from one of the following:

[0117] (1) An organic electroluminescent device comprises an anode, a hole injection layer, a first hole transport layer, a light-emitting layer, a first electron transport layer, and a cathode stacked in sequence, that is, anode / hole injection layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode. The device structure will be expressed in this simplified manner below.

[0118] (2) anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode.

[0119] (3) anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / cathode.

[0120] (4) anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / electron injection layer / cathode.

[0121] (5) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / multilayer cathode.

[0122] (6) anode / hole injection layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / cathode.

[0123] (7) anode / hole injection layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / second electron transport layer / cathode.

[0124] (8) anode / hole injection layer / second hole transport layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / cathode.

[0125] (9) anode / hole injection layer / second hole transport layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / second electron transport layer / cathode.

[0126] (10) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode.

[0127] (11) anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode.

[0128] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode.

[0129] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / cathode (device structure of the red and green light device embodiments of the present application).

[0130] The light emission direction of the organic electroluminescent device can be emitted from the anode side or the cathode side. In some specific embodiments, if the light emission direction is from the cathode side, it is necessary to add another covering layer on the cathode side. The specific structure is as follows:

[0131] 1) Anode / hole injection layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode / covering layer.

[0132] 2) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode / covering layer.

[0133] 3) anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / cathode / covering layer.

[0134] 4) anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / electron injection layer / cathode / covering layer.

[0135] 5) anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / second electron transport layer / multilayer cathode / covering layer.

[0136] 6) anode / hole injection layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / cathode / covering layer.

[0137] 7) anode / hole injection layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / second electron transport layer / cathode / covering layer.

[0138] 8) anode / hole injection layer / second hole transport layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / cathode / covering layer.

[0139] 9) anode / hole injection layer / second hole transport layer / first hole transport layer / first light-emitting layer / carrier generation layer / first hole transport layer / second light-emitting layer / first electron transport layer / second electron transport layer / cathode / covering layer.

[0140] 10) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode / covering layer.

[0141] 11) Anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode / covering layer.

[0142] 12) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode / covering layer.

[0143] 13) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / cathode / covering layer (device structure of the blue light embodiment of the present application).

[0144] Some specific functional layers in the organic electroluminescent device will be described below.

[0145] Substrate:

[0146] The substrate is generally located below the anode, and the substrate may be made of plastic or glass, and may be rigid or bendable. The substrate is provided with a driving unit, which may drive the corresponding pixel to emit light.

[0147] anode:

[0148] Organic EL (Organic Electro-Luminescence) components usually have requirements for the anode to have good conductivity, a flat surface, and not prone to cracks. At the same time, there are certain requirements for the work function, mainly to be able to match the hole injection layer and exert the hole injection effect.

[0149] When the top emission mode (light emitting from the cathode side) is adopted, the anode adopts a metal compound with a work function of 4.2eV or more, such as indium tin oxide alloy, tin oxide, indium zinc oxide, gold, silver, platinum, copper, carbon nanotubes, carbon nanowires, graphene, etc. The thickness is 10nm to 200nm, preferably 10nm to 50nm. A reflective electrode is set under the anode (close to the substrate end). The reflective electrode is generally made of metal or metal alloy, such as silver metal, copper metal, aluminum metal, gold metal or alloys of these metals and other metals. The reflectivity of the reflective electrode is relatively high, and the reflectivity is required to be above 90%. The thickness is usually used at a thickness of 100nm to 500nm, preferably in the range of 80nm to 150nm.

[0150] When the bottom emission mode (light emitting from the negative substrate side) is adopted, the anode adopts a metal compound with a work function of 4.2eV or more, for example, indium tin oxide alloy, tin oxide, indium zinc oxide, gold, silver, platinum, copper, carbon nanotubes, carbon nanowires, graphene, etc. The thickness is 10nm to 1μm, preferably 50nm to 200nm.

[0151] The anode can be produced by forming an electrode material into a thin film by a method such as vapor deposition, sputtering, or coating.

[0152] Hole injection layer:

[0153] The thickness of the hole injection layer is generally 3nm to 20nm. The hole injection layer is a mixture of P-type materials and hole transport materials. The purpose of using P-type materials is to receive holes from the anode and transfer them to the hole transport material. The weight proportion of P-type materials in the hole injection layer is generally 0.5% to 10%. When the weight proportion is 0.5% to 3%, the absolute value of the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the P-type material and the highest occupied molecular orbital (HOMO) energy level of the HTL material shall not be greater than 0.3eV. When the weight proportion is 3% to 5%, the absolute value of the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the P-type material and the highest occupied molecular orbital (HOMO) energy level of the HTL material shall not be greater than 0.5eV. When the weight proportion is 5% to 10%, the absolute value of the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the P-type material and the highest occupied molecular orbital (HOMO) energy level of the HTL material shall not be greater than 1eV.

[0154] The P-type material can be made of metal oxides, such as molybdenum oxide, vanadium oxide, tungsten oxide, etc.; it can also be made of organic matter, such as 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-trimethylene tris(cyanoformylidene))tris(2,3,5,6-tetrafluorobenzyl) (PD1, CAS No.: 1224447-88-4), tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), and is not limited thereto. The hole transport material matched with the P-type material can be selected from the material of the second hole transport layer, and can be the same as the material of the second hole transport layer or different.

[0155] Second hole transport layer:

[0156] The thickness of the second hole transport layer is generally 40nm to 150nm, and aromatic amine compounds are often used, which can be aromatic monoamines or aromatic polyamines. The hole transport material is required to have high hole mobility, be able to reduce the driving voltage, and have a glass transition temperature exceeding 100°C to avoid crystallization at high temperatures.

[0157] First hole transport layer:

[0158] The thickness of the first hole transport layer is generally 3nm to 220nm. When there is no second hole transport layer, the thickness of the first hole transport layer is generally 40nm to 150nm; when there is a second hole transport layer, the thickness of the first hole transport layer is generally 3nm to 120nm. In general, red light, green light, blue light, yellow light, etc. need to be adjusted in thickness according to the "microcavity effect", and the thickness selection is also different. Taking the top-emitting light-emitting device as an example, the formula for the microcavity is as follows:

[0159]

[0160] where n i ,d i Respectively indicate the refractive index and thickness of the i-th layer, m is an integer, which is the modulus of the microcavity, and is more commonly 1 or 2; θ 1 ,θ 2 They represent the phase shift of light at the anode interface and the cathode interface respectively.

[0161] Red light, green light, blue light or other colors of light have different wavelengths, so each color has its optimal thickness. Taking the modulus of 2 as an example, for red light, when there is no second hole transport layer, the thickness of the first hole transport layer is generally 160nm~220nm; when there is a second hole transport layer, the thickness of the first hole transport layer is generally 8nm~120nm. For green light, when there is no second hole transport layer, the thickness of the first hole transport layer is generally 100nm~180nm; when there is a second hole transport layer, the thickness of the first hole transport layer is generally 30nm~70nm. For blue light, when there is no second hole transport layer, the thickness of the first hole transport layer is generally 80nm~130nm; when there is a second hole transport layer, the thickness of the first hole transport layer is generally 3nm~30nm. When other colors are selected, there will be different optimal "microcavity adjustment thicknesses".

[0162] Electron blocking layer:

[0163] The electron blocking layer can have both hole transport and electron blocking functions. At the same time, the higher triplet excitation energy level of the electron blocking layer can lock the excitons generated in the light-emitting layer in the light-emitting layer, thereby improving the luminous efficiency of the device.

[0164] Luminous layer:

[0165] The material of the light-emitting layer generally includes a host material and a guest dopant material. The content of the host material is greater than that of the guest dopant material. Optionally, the mass percentage of the guest dopant material in the light-emitting layer is 1% to 20%.

[0166] The guest doping material as the luminescent material may include phosphorescent or fluorescent materials or thermally activated delayed fluorescent materials, and red light, green light, and blue light may be selected from the above three guest doping materials. For example, the guest doping material of the luminescent layer corresponding to the luminescent unit with a red luminescent color and the luminescent layer corresponding to the luminescent unit with a green luminescent color is a phosphorescent material, and the guest doping material of the luminescent layer corresponding to the luminescent unit with a blue luminescent color is a fluorescent material.

[0167] Or for example, the guest doping material of the light-emitting layer corresponding to the light-emitting unit with red light-emitting color and the light-emitting layer corresponding to the light-emitting unit with green light-emitting color is a phosphorescent material, and the guest doping material of the light-emitting layer corresponding to the light-emitting unit with blue light-emitting color is a phosphorescent material.

[0168] Or for example, the guest doping material of the light-emitting layer corresponding to the light-emitting unit with red light-emitting color and the light-emitting layer corresponding to the light-emitting unit with green light-emitting color is a thermally activated delayed fluorescent material, and the guest doping material of the light-emitting layer corresponding to the light-emitting unit with blue light-emitting color is a fluorescent material.

[0169] Or for example, the guest doping material of the light-emitting layer corresponding to the light-emitting unit with red light-emitting color and the light-emitting layer corresponding to the light-emitting unit with green light-emitting color is a thermally activated delayed fluorescent material, and the guest doping material of the light-emitting layer corresponding to the light-emitting unit with blue light-emitting color is a phosphorescent material.

[0170] In order to reduce the power consumption of the organic light-emitting display panel in the organic electroluminescent device, the guest doping material can be selected to have excellent light-emitting performance. Taking the top-emitting device as an example, optionally, the light-emitting unit with a red light-emitting color has a light-emitting brightness of 1000 cd / m 2 The current efficiency is greater than 30cd / A, and the green luminous unit has a luminous brightness of 6000cd / m 2 The current efficiency is greater than 100cd / A, and the light-emitting unit with fluorescent blue light color has a light brightness of 1000cd / m 2 The current efficiency is greater than 5cd / A as the standard, and the appropriate guest doping material is selected. The light-emitting unit with a phosphorescent blue light color has a light-emitting brightness of 1000cd / m 2 The current efficiency is greater than 10cd / A. When the current efficiency is higher, the power consumption can be reduced.

[0171] As the light-emitting host material, one light-emitting host material or two light-emitting host materials may be selected.

[0172] Hole blocking layer:

[0173] In order to enhance the balance of hole and electron concentrations, a hole blocking layer is inserted to balance the carrier concentration and prevent exciton quenching. Generally, the hole blocking layer is located between the light-emitting layer and the electron transport layer. The hole blocking layer material must meet the conditions of strong stability, good film-forming properties, and a sufficiently high highest molecular occupied orbital.

[0174] First electron transport layer:

[0175] The thickness of the first electron transport layer can generally be 3nm to 40nm, 3nm to 10nm, 10nm to 20nm, 20nm to 30nm, 30nm to 40nm or 20nm to 40nm, etc. When there is no second electron transport layer, the thickness of the first electron transport layer is generally 20nm to 50nm, and when there is a second electron transport layer, the thickness of the first electron transport layer is generally 40nm to 20nm. The first electron transport layer is in direct contact with the light-emitting layer, so similar to the first hole transport layer, electronic changes will also occur during the electron transport process, resulting in increased molecular vibration and molecular deformation. It will also be because the excitons of the light-emitting layer interact with the polarons of the electron transport material. This action is likely to produce active free radicals and destroy the electron transport material. The electron transport material can be a single compound or mixed with other metals or metal compounds. It can include a mixture of organic electron transport materials and metal compounds, or a mixture of organic electron transport materials and metals.

[0176] When the organic electron transport material is mixed with a metal compound material, for example, it is mixed with an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, and more specifically, it is mixed with a metal lithium compound, a metal calcium compound, a metal Mg compound, a metal samarium compound, a metal ytterbium compound, and more specifically, it is mixed with 8-hydroxyquinoline lithium, lithium fluoride, magnesium fluoride, ytterbium fluoride, calcium fluoride, etc. When mixed with a metal compound, the mass proportion of the organic electron transport material can be 20% to 80%, 20% to 40%, 40% to 60%, or 60% to 80%, etc.

[0177] When the organic electron transport material is mixed with a metal, for example, mixed with an alkali metal, an alkaline earth metal, or a rare earth metal, more specifically, mixed with lithium metal, magnesium metal, calcium metal, ytterbium metal, samarium metal, etc., when mixed with a metal, the mass proportion of the organic electron transport material can be 80% to 99%, 80% to 89%, 89% to 99%, 80% to 85%, 85% to 90%, 90% to 95%, or 95% to 99%, etc.

[0178] Second electron transport layer:

[0179] The thickness of the second electron transport layer is generally 10 nm to 40 nm, and the material of the second electron transport layer may include a mixture of an organic electron transport material and a metal compound, or a mixture of an organic electron transport material and a metal.

[0180] When the organic electron transport material is mixed with a metal compound material, for example, it is mixed with an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, and more specifically, it is mixed with a metal lithium compound, a metal calcium compound, a metal Mg compound, a metal samarium compound, a metal ytterbium compound, and more specifically, it is mixed with 8-hydroxyquinoline lithium, lithium fluoride, magnesium fluoride, ytterbium fluoride, calcium fluoride, etc. When mixed with a metal compound, the mass proportion of the organic electron transport material can be 20% to 80%, 20% to 40%, 40% to 60%, or 60% to 80%, etc.

[0181] When the organic electron transport material is mixed with a metal, for example, mixed with an alkali metal, an alkaline earth metal, or a rare earth metal, more specifically, mixed with lithium metal, magnesium metal, calcium metal, ytterbium metal, samarium metal, etc., when mixed with a metal, the mass proportion of the organic electron transport material can be 80% to 99%, 80% to 89%, 89% to 99%, 80% to 85%, 85% to 90%, 90% to 95%, or 95% to 99%, etc.

[0182] Charge generation layer:

[0183] When a single-layer light-emitting layer device is used, holes and electrons are injected from the anode and cathode respectively, and a charge generation layer is not required. When a double-layer or multi-layer light-emitting layer is used, a charge generation layer is required between the light-emitting layers to achieve the effect of charge generation, injection and transmission. The charge generation layer is located between the two light-emitting layers, and is generally composed of two layers of P / N type materials, wherein the P-type material is selected from the hole injection material mentioned above, and the N-type material is mixed with an organic electron transport material doped with a metal. The organic electron transport layer material is selected from the second electron transport layer mentioned above, and the metal is selected from alkali metals, alkaline earth metals, and rare earth metals, and more specifically, lithium metal, magnesium metal, calcium metal, ytterbium metal, samarium metal, etc. When the organic electron transport material is mixed with the metal, the mass proportion of the organic electron transport material can be 80% to 99%, 80% to 89%, 89% to 99%, 80% to 85%, 85% to 90%, 90% to 95%, or 95% to 99%, etc.

[0184] cathode:

[0185] The cathode requires a material with good electrical conductivity and good surface flatness. In order to improve the electron injection capability, a material with a small work function is usually selected. The cathode material can be a single-layer cathode, or a double-layer or multi-layer cathode, generally a metal or a metal alloy. For a single-layer cathode, silver, copper, aluminum, gold, or alloys of these metals with other metals, such as alloys with rare earth metals, alkali metals, and alkaline earth metals, can be used, which can be listed as magnesium-indium alloy, magnesium-aluminum alloy, aluminum-potassium alloy, aluminum-scandium-potassium alloy, magnesium-silver alloy, silver-ytterbium alloy, silver-samarium alloy, etc. If the cathode uses a double-layer metal, the cathode near the light-emitting layer can use alkali metals, alkaline earth metals, rare earth metals, etc., such as lithium, calcium, magnesium, ytterbium, etc., to increase the electron injection ability, and the cathode layer far from the light-emitting side is mainly used to improve the conductivity. Generally, silver, copper, aluminum, gold or alloys of these metals with other metals, such as alloys with rare earth metals, alkali metals, and alkaline earth metals can be used, which can be listed as magnesium-indium alloy, magnesium-aluminum alloy, aluminum-potassium alloy, aluminum-scandium-potassium alloy, magnesium-silver alloy, silver-ytterbium alloy, silver-samarium alloy, etc. The cathode can also be formed into a thin film by evaporation, sputtering, etc.

[0186] When light comes out from the anode side, the cathode is required to be light-proof, and a cathode with a thickness greater than 100nm can be evaporated. When light comes out from the cathode side, the cathode is required to be transparent, and the transmittance should be greater than 40% at this time, and the thickness should be 10nm to 20nm.

[0187] Overlay:

[0188] The refractive index n and absorption coefficient of the single-layer cover layer need to meet the following conditions:

[0189] The refractive index between the wavelengths of 450 and 650 nm is n(450-650nm)>1.8, and the extinction coefficient between the wavelengths of 450 and 650nm is below 0.1; the extinction coefficient at 380nm is greater than 0.2; the difference between the refractive index of 450nm and the refractive index of 530nm is n(450nm)-n(530nm)<0.5, more preferably n(450nm)-n(530nm)<0.3; the difference between the refractive index of 510nm and the refractive index of 620nm is n(510nm)-n(620nm)<0.4, more preferably the difference between the refractive index of 510nm and the refractive index of 620nm is n(510nm)-n(620nm)<0.2.

[0190] The material that can meet the requirements of the cover layer for the refractive index n can further achieve high luminous efficiency of the device, while the light output efficiency and viewing angle of red light, green light and blue light are more balanced.

[0191] In some specific embodiments, the thickness of the covering layer is 50nm to 90nm, for example, 50nm, 55nm, 57nm, 59nm, 62nm, 64nm, 67nm, 68nm, 70nm, 75nm, 77nm, 79nm, 80nm, 82nm, 85nm, 88nm, 90nm, etc.

[0192] The covering layer is formed after the semi-transparent cathode of the OLED display panel is away from the substrate, so that the light transmittance of the stacked layer formed by the covering layer and the semi-transparent cathode between 450nm and 650nm is ≥65%, for example, 68%, 69%, 73%, 77%, 79%, 83%, 88%, 93%, etc.

[0193] When two layers of cover are used, the refractive index n and the absorption coefficient need to meet the following conditions:

[0194] The covering layer close to the cathode side (the first covering layer) has a refractive index n450~650nm<1.8 between 450 and 650nm, and an extinction coefficient between 450 and 650nm below 0.1; the maximum coefficient at any wavelength between 250nm and 350nm is greater than 0.3, and optimally greater than 0.6.

[0195] The covering layer (second covering layer) away from the cathode side has a refractive index n450~650nm>1.8 between 450 and 650nm, and an extinction coefficient between 450 and 650nm is below 0.1; the extinction coefficient at 380nm is greater than 0.1, and more preferably greater than 0.2.

[0196] The difference between the refractive index at 450 nm and the refractive index at 530 nm is n(450 nm)-n(530 nm)<0.5, and more preferably, the difference between the refractive index at 450 nm and the refractive index at 530 nm is n(450 nm)-n(530 nm)<0.3;

[0197] The difference between the refractive index at 510 nm and the refractive index at 620 nm is n(510 nm)-n(620 nm)<0.4, and more preferably, the difference between the refractive index at 450 nm and the refractive index at 530 nm is n(450 nm)-n(530 nm)<0.2.

[0198] The total thickness of the double-layer covering layer is 50nm to 90nm, for example: 50nm, 55nm, 57nm, 59nm, 62nm, 64nm, 67nm, 68nm, 70nm, 75nm, 77nm, 79nm, 80nm, 82nm, 85nm, 88nm, 90nm, etc.

[0199] The thickness of the covering layer (first covering layer) close to the cathode side is 5nm to 40nm, for example: 5nm, 7nm, 10nm, 12nm, 15nm, 18nm, 20nm, 22nm, 25nm, 27nm, 30nm, 32nm, 34nm, 36nm, 38nm, 40nm, etc.

[0200] The thickness of the covering layer (second covering layer) away from the cathode side is 35nm to 85nm, for example: 35nm, 40nm, 43nm, 45nm, 48nm, 50nm, 55nm, 57nm, 59nm, 62nm, 64nm, 67nm, 68nm, 70nm, 75nm, 77nm, 79nm, 80nm, 82nm, 85nm, etc.

[0201] On the other hand, the present application further provides a display device, comprising the above-mentioned organic electroluminescent device.

[0202] Synthesis Example:

[0203] The specific preparation method of the above-mentioned new compound of the present invention will be described in detail below by taking multiple synthesis examples as examples, but the preparation method of the present invention is not limited to these multiple synthesis examples. Those skilled in the art can make any modifications, equivalent substitutions, improvements, etc. on this basis without departing from the principles of the present invention, and expand the method to the scope of the technical solution claimed for protection by the claims of the present invention.

[0204] Synthesis and testing methods

[0205]

Raw materials and reagents

[0206] The initial raw materials and solvents of the present invention were purchased from Shanghai Titan Technology Co., Ltd., some commonly used OLED intermediates and other products were purchased from domestic OLED intermediate manufacturers; various palladium catalysts, ligands, etc. were purchased from Shaanxi Ruike New Materials Co., Ltd.

[0207]

Cross-coupling synthesis

[0208] The synthesis of the bistriarylamine compound represented by the above formula (a) can be carried out using known methods. For example, a cross-coupling reaction using transition metals such as nickel and palladium. Other synthesis methods are CC, CN coupling reactions using transition metals such as magnesium or zinc. The above reactions are limited to the characteristics of mild reaction conditions and superior selectivity of various functional groups, and preferably Suzuki and Buchwald reactions. The cycloalkane and heterocycloalkane derivatives of the present invention are illustrated by the following examples, but are not limited to the cycloalkane and heterocycloalkane derivatives and synthesis methods illustrated in these examples.

[0209] In an inert atmosphere, reaction A and the reactants are heated in an organic solvent in the presence of a cross-coupling catalyst (catalytic amount), and reflux heating and stirring are performed during the reaction. After the desired reaction time, the reaction system is cooled and water is added, and the precipitated solid is washed and vacuum dried to obtain a crude product. The obtained crude product is refined (including but not limited to silica gel column chromatography) to obtain a product.

[0210]

Test method

[0211] 1 H NMR data were measured using a (400 MHz) nuclear magnetic resonance instrument (manufactured by Bruker, Germany); HPLC data were measured using a Waters Corporation UPLC ultra-high performance liquid chromatograph. Mass spectra were measured using a Waters Corporation single quadrupole mass spectrometer.

[0212] Synthesis of compound 1:

[0213]

[0214] Synthesis of compound 1-ii:

[0215] Under nitrogen atmosphere, 2-chloro-9H-fluorene (compound 1-i, 10.0g, 50.0mmol, 1eq), sodium tert-butoxide (14.4g, 150.0mmol, 3eq) and N,N-dimethylformamide (300mL) were added to a three-necked flask in sequence and stirred at room temperature for 30 minutes. Subsequently, 2,2'-dibromodiethyl ether (13.9g, 60.0mmol, 1,2eq) was slowly added at 0°C. After the addition was completed, the reaction system was slowly restored to room temperature and continued to stir at room temperature for 4 hours. Thin layer chromatography analysis showed that there was basically no raw material remaining. Deionized water (500mL) and ethyl acetate (250mL) were added to the reaction system in sequence, and the mixture was allowed to stand for stratification after stirring for 5 minutes. The organic phase was collected, the aqueous phase was extracted with ethyl acetate (3x60mL), the resulting organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by reduced pressure distillation. The obtained crude product was separated by rapid silica gel column chromatography (the mobile phase was a mixed solvent of n-hexane / ethyl acetate) to obtain compound 1-ii (11.0 g, yield 82.1%).

[0216] Synthesis of compound 1:

[0217] In a nitrogen atmosphere, compound 1-ii (5.4 g, 20.0 mmol, 1 eq), di(4-biphenyl)amine (compound 1-vi, 6.4 g, 20.0 mmol, 1 eq) and degassed anhydrous toluene (100 mL) were added to a dry three-necked flask in sequence. After thorough mixing, sodium tert-butoxide (2.9 g, 30.0 mmol, 1.5 eq), bis(dibenzylideneacetone palladium) (113 mg, 0.2 mmol, 1% eq), and tri-tert-butylphosphine (1.0 mL, 10% n-hexane solution, 0.4 mmol, 2% eq) were added respectively. Stirring was started, the above reaction system was thoroughly mixed, and the temperature was raised to reflux under a nitrogen atmosphere. After reacting for 7 hours, there was basically no raw material remaining by thin layer chromatography analysis, and heating was stopped. After the temperature of the reaction system dropped to room temperature, a mixed solution of 5 mL of concentrated hydrochloric acid (37% aqueous solution) and 100 mL of deionized water was added thereto, and the layers were allowed to stand for separation. The organic phase was retained, and the aqueous phase was extracted with toluene (3×20 mL), combined with the above-retained organic phase, and the solvent was removed by reduced pressure distillation. The crude product was separated by silica gel column chromatography (the mobile phase was a mixed solvent of n-hexane / toluene) and recrystallized (ethanol / n-hexane mixed solvent) to obtain the target compound 1 (8.5 g, yield 76.5%). The total yield of the two-step reaction was 62.8%. Mass spectrum (m / z) = 556.26 [M+H] + .

[0218] When L is not a single bond, and / or Ra exists, fluorene substituted with halogen at the corresponding position can be selected as a raw material compound, and the corresponding intermediate is synthesized by Suzuki coupling reaction, and then the target compound is obtained by referring to the preparation method of compound 1. The following is an example of compound 23:

[0219]

[0220] Referring to the preparation method of compound 1, the compounds listed in Table 1 were synthesized. For each compound x, the raw materials or intermediate compounds 1-i and 1-iii involved in the above preparation method are represented by xi and x-iii, respectively. Among them, the main raw materials used, the synthesized intermediates, the yields and the mass spectrometry characterization data are shown in Table 1.

[0221] Table 1

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232] The NMR data of the representative compounds involved in the synthesis examples are shown in Table 2.

[0233] Table 2

[0234]

[0235]

[0236] Device Example:

[0237] The compounds used in the device are all purified by sublimation, and the purity is greater than 99.98%.

[0238] The compound involved in the present invention can be used as hole transport layer or electron blocking layer material of OLED devices with various colors such as blue light, green light, red light, etc. The specific device manufacturing method and test results are given below.

[0239] Preparation of blue organic electroluminescent devices (as hole transport layer material)

[0240] Blue light device embodiment 1:

[0241] According to Figure 1The structure shown is used to make a blue top-emitting organic electroluminescent device, and the preparation process is as follows: on a glass substrate 101, a transparent ITO film layer (thickness 150nm) is formed by a magnetron sputtering process to obtain a first electrode 102 as an anode. A mixed material of compound M1 and compound M2 is evaporated on the surface of the anode as a hole injection layer 103, with a mixing ratio of 3:97 (mass ratio) and a thickness of 10nm; then, compound 1 of the present invention (thickness 100nm) and compound M2-B (thickness 20nm) are sequentially evaporated on the surface of the hole injection layer to obtain a hole transport layer 104 and an electron blocking layer 105, respectively. Next, on the surface of the electron blocking layer 105, compound M3-B and compound M4-B are co-evaporated at a mass ratio of 95:5 to form an organic light-emitting layer 106 (thickness 30nm). Subsequently, compound M5 was sequentially evaporated on the surface of the organic light-emitting layer to form a hole blocking layer 107 (thickness 10 nm), and compound M6 and LiQ with a mixing ratio of 4:6 (mass ratio) formed an electron transport layer 108 (thickness 30 nm). Subsequently, magnesium (Mg) and silver (Ag) were mixed and deposited on the surface of the electron transport layer 108 at an evaporation rate of 1:9 to form a second electrode 109 with a thickness of 10 nm as a cathode. Finally, compound M7 with a thickness of 70 nm was evaporated as a covering layer to complete the manufacture of the organic light-emitting device.

[0242] During the device preparation process, the vacuum degree was maintained at 2×10 -7 Torr to 5×10 -6 Torr; the evaporation rate of organic matter is between to The evaporation rate of aluminum is

[0243] The chemical structures of the compounds M1, M2, M2-B, M3-B, M4-B, M5, M6, M7 and LiQ are shown in Table 3:

[0244] Table 3

[0245]

[0246] Blue light device embodiment 2-12

[0247] The organic electroluminescent device was prepared by the same method as in Example 1 of the blue light device, except that the compounds in Table 4 were used to replace Compound 1 when forming the hole transport layer.

[0248] Comparative Example 1-2

[0249] The organic electroluminescent device was prepared in the same manner as in Example 1 of the blue light device, except that the compound 1 was replaced by the compound HT1 and the compound HT2 respectively when forming the hole transport layer.

[0250] The chemical structures of the compounds HT1 and HT2 are shown below:

[0251]

[0252] For the organic electroluminescent device prepared as above, its operating voltage and efficiency were calculated by a computer-controlled Keithley 2400 test system. The device life under dark conditions was obtained using a Foster life measurement system equipped with a power supply and a photodiode as a detection unit. LT95 represents the time required for the device brightness to decay to 95% of the initial brightness. The test results are shown in Table 4.

[0253] Table 4

[0254]

[0255]

[0256] Preparation of blue organic electroluminescent devices (as electron blocking layer material)

[0257] Blue light device embodiments 13-23:

[0258] The organic electroluminescent device was prepared in the same manner as in Comparative Example 2 of the blue light device, except that the compound M2-B was replaced by the compounds in Table 5 below when forming the electron blocking layer.

[0259] Comparative Examples 3-4:

[0260] The organic electroluminescent device was prepared in the same manner as in Comparative Example 2 of the blue light device, except that the compound BP1 and BP2 were used to replace the compound M2-B when forming the electron blocking layer.

[0261] The chemical structures of the compounds BP1 and BP2 are shown below:

[0262]

[0263] For the organic electroluminescent device prepared as above, its operating voltage and efficiency are calculated by a computer-controlled Keithley 2400 test system. The device life under dark conditions is obtained using a Foster life measurement system equipped with a power supply and a photodiode as a detection unit. LT95 represents the time required for the device brightness to decay to 95% of the initial brightness. The test results are shown in Table 5.

[0264] Table 5

[0265]

[0266]

[0267] Preparation of red organic electroluminescent devices (as electron blocking layer material)

[0268] Red light device embodiment 1:

[0269] According to Figure 2 The structure shown is used to make a red bottom-emitting organic electroluminescent device, and the preparation process is as follows: on a glass substrate 101, a transparent ITO film layer (thickness 150nm) is formed by a magnetron sputtering process to obtain a first electrode 102 as an anode. A mixed material of compound M1 and compound HT2 is evaporated on the surface of the anode as a hole injection layer 103, with a mixing ratio of 3:97 (mass ratio) and a thickness of 10nm; then compound HT1 (thickness 100nm) and compound 2 of the present invention (thickness 20nm) are sequentially evaporated on the surface of the hole injection layer to obtain a hole transport layer 104 and an electron blocking layer 105, respectively. Next, on the surface of the second hole transport layer 105, compound M3-R and compound M4-R are co-evaporated at a mass ratio of 95:5 to form an organic light-emitting layer 106 (thickness 40nm). Subsequently, compound M5 is sequentially evaporated on the surface of the organic light-emitting layer to form a hole blocking layer 107 (thickness 10 nm), and compound M6 and LiQ with a mixing ratio of 4:6 (mass ratio) are formed to form an electron transport layer 108 (thickness 30 nm). Finally, magnesium (Mg) and silver (Ag) are mixed and deposited on the surface of the electron transport layer 108 at an evaporation rate of 1:9 to form a second electrode 109 with a thickness of 10 nm as a cathode, completing the manufacture of the organic light-emitting device.

[0270] During the device preparation process, the vacuum degree was maintained at 2×10 -7 Torr to 5×10 -6 Torr; the evaporation rate of organic matter is between to The evaporation rate of aluminum is

[0271] The chemical structures of compounds HT1, M5, M6, M7 and LiQ are as described above, and the chemical structures of compounds M3-R and M4-R are shown in Table 6.

[0272] Table 6

[0273]

[0274]

[0275] Red light device embodiment 2-15

[0276] The organic electroluminescent device was prepared by the same method as in Example 1 of the red light device, except that the compounds in Table 7 below were used to replace Compound 2 when forming the electron blocking layer.

[0277] Comparative Examples 5-6

[0278] The organic electroluminescent device was prepared in the same manner as in Example 1 of the red light device, except that the compound RP1 and RP2 were used to replace the compound 2 when forming the resistance barrier layer.

[0279] The chemical structures of compounds RP1 and RP2 are shown below:

[0280]

[0281] For the organic electroluminescent device prepared as above, its operating voltage and efficiency are calculated by a computer-controlled Keithley 2400 test system. The device life under dark conditions is obtained using a Foster life measurement system equipped with a power supply and a photodiode as a detection unit. LT95 represents the time required for the device brightness to decay to 95% of the initial brightness. The test results are shown in Table 7.

[0282] Table 7

[0283]

[0284]

[0285] Preparation of green organic electroluminescent devices (as electron blocking layer material)

[0286] Green light device embodiment 1:

[0287] According to Figure 2The structure shown is used to make a green bottom-emitting organic electroluminescent device, and the preparation process is as follows: on a glass substrate 101, a transparent ITO film layer (thickness 150nm) is formed by a magnetron sputtering process to obtain a first electrode 102 as an anode. A mixed material of compound M1 and compound HT2 is evaporated on the surface of the anode as a hole injection layer 103, with a mixing ratio of 3:97 (mass ratio) and a thickness of 10nm; then compound HT1 (thickness 100nm) and compound 3 of the present invention (thickness 40nm) are sequentially evaporated on the surface of the hole injection layer to obtain a hole transport layer 104 and an electron blocking layer 105, respectively. Next, on the surface of the second hole transport layer 105, compound M3-PG, compound M3-NG and compound M4-G are co-evaporated at a mass ratio of 45:45:10 to form an organic light-emitting layer 106 (thickness 40nm). Subsequently, compound M5 is sequentially evaporated on the surface of the organic light-emitting layer to form a hole blocking layer 107 (thickness 10 nm), and compound M6 and LiQ with a mixing ratio of 4:6 (mass ratio) are formed to form an electron transport layer 108 (thickness 30 nm). Finally, magnesium (Mg) and silver (Ag) are mixed and deposited on the surface of the electron transport layer 108 at an evaporation rate of 1:9 to form a second electrode 109 with a thickness of 10 nm as a cathode, completing the manufacture of the organic light-emitting device.

[0288] During the device preparation process, the vacuum degree was maintained at 2×10 -7 Torr to 5×10 -6 Torr; the evaporation rate of organic matter is between to The evaporation rate of aluminum is

[0289] The chemical structures of compounds HT1, M5, M6, M7 and LiQ are as described above, and the chemical structures of compounds M3-PG, M3-NG, and M4-G are shown in Table 8.

[0290] Table 8

[0291]

[0292] Green light device embodiment 2-15

[0293] The organic electroluminescent device was prepared by the same method as in Example 1 of the green light device, except that the compounds in Table 9 below were used to replace Compound 3 when forming the electron blocking layer.

[0294] Comparative Examples 7-8

[0295] The organic electroluminescent device was prepared in the same manner as in Example 1 of the green light device, except that the compound 3 was replaced by the compounds GP1 and GP2 when forming the electron blocking layer.

[0296] The chemical structures of compounds GP1 and GP2 are shown below.

[0297]

[0298] For the organic electroluminescent device prepared as above, its operating voltage and efficiency are calculated by a computer-controlled Keithley 2400 test system. The device life under dark conditions is obtained using a Foster life measurement system equipped with a power supply and a photodiode as a detection unit. LT95 represents the time required for the device brightness to decay to 95% of the initial brightness. The test results are shown in Table 9.

[0299] Table 9

[0300]

[0301]

[0302] It can be seen from Tables 4, 5, 7 and 9 that the triarylamine compounds based on 2',3',5',6'-tetrahydrospiro[fluorene-9,4'-pyran] provided by the present invention are applied to the hole transport layer or electron blocking layer of blue, red and green organic electroluminescent devices. Compared with the corresponding comparative example compounds, the various performance indicators of the devices (such as operating voltage, current efficiency and life span, etc.) are improved to varying degrees.

[0303] The present invention provides each embodiment compound, it is characterised in that tetrahydropyran is introduced to replace at the 9-position of fluorenyl to form a spirocyclic structure. On the one hand, the spirocyclic structure has a strong steric hindrance effect, which is conducive to the promotion of the triplet energy level of the molecule, and is also conducive to the formation of a continuous and uniform amorphous film in the macroscopic state of the molecule, and maintains a stable film morphology when the device works for a long time to generate a large amount of Joule heat, that is, it is conducive to the stability improvement of the device. On the other hand, the oxygen atom in the tetrahydropyran fragment has both the inductive effect of electron withdrawal and the hyperconjugation effect of electron donation, and this fragment is introduced into the fluorenyl, which can further enhance the electron donation and stability of the fluorenyl, and correspondingly, the present invention comprising this fluorenyl provides each embodiment compound, with a strong hole transport ability and molecular stability, so as to be conducive to the device operating voltage reduction, current efficiency and lifespan improvement. Thirdly, by adjusting the different substituents connected to the aromatic amine group and / or the fluorene group, the frontier orbital energy level and triplet energy level of the molecule can be effectively regulated, making it selectively adaptable to the hole transport layer material or electron blocking layer material of a variety of color organic electroluminescent devices.

[0304] For example, in a blue light organic electroluminescent device, in Table 4, the difference between the comparative compound HT1 and the example compound 1 is that one methylene group in the cyclohexane fragment in the fluorene group is replaced by an oxygen atom, and correspondingly, the working voltage of the example device is reduced by 4.1%, the current efficiency is increased by 3.6%, and the life span is increased by 55.4%. In Table 5, the difference between the comparative compound BP1 and the example compound 10 is that a diphenyl group in the compound BP1 is replaced by a fluorene group containing a tetrahydropyran fragment, and correspondingly, the working voltage of the example device is reduced by 7.2%, the current efficiency is increased by 7.8%, and the life span is increased by 52.8%. In Table 7 of the red light organic electroluminescent device, the difference between the comparative compound RP1 and the example compound 2 is that the dimethyl group on the fluorene group is replaced by tetrahydropyran, and correspondingly, the working voltage of the example device is reduced by 8.5%, the current efficiency is increased by 25.3%, and the life span is increased by 15.8%. Similarly, in Table 9 of green organic electroluminescent devices, the working voltage of the example device is reduced by 9.2%, the current efficiency is increased by 11.8%, and the life is increased by 34.7% compared with the example compound 5 of the comparative example compound GP1. The difference between the comparative example compound GP2 and the example compound 4 is that the biphenyl group on the fluorene group is replaced by tetrahydropyran, and correspondingly, the working voltage of the example device is reduced by 11.1%, the current efficiency is increased by 12.7%, and the life is increased by 30.4%.

[0305] These results indicate that the triarylamine compound based on 2',3',5',6'-tetrahydrospiro[fluorene-9,4'-pyran] provided by the present invention can effectively achieve further improvement in device performance.

[0306] In summary, the present invention effectively overcomes various shortcomings of the prior art and has high industrial utilization value.

[0307] The above is only a preferred embodiment of the present invention, and is not any formal or substantial limitation of the present invention. It should be pointed out that ordinary technicians in this technical field can make several improvements and supplements without departing from the method of the present invention, and these improvements and supplements should also be regarded as the protection scope of the present invention. Any technician familiar with this profession, without departing from the spirit and scope of the present invention, can make some changes, modifications and evolutions of the technical content disclosed above, which are equivalent embodiments of the present invention; at the same time, any changes, modifications and evolutions of any equivalent changes made to the above embodiments based on the essential technology of the present invention are still within the scope of the technical solution of the present invention.

Claims

1. A triarylamine compound, wherein the triarylamine compound has a structure as shown in formula (a): in, R1 to R8 are the same as or different from each other and are each independently selected from H or D; L, L1, L2 are the same or different from each other, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms; Ar1 and Ar2 are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms; Each occurrence of R is independently selected from deuterium, cyano, nitro, halogen, trifluoromethyl, deuterated methyl, straight or branched chain alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkenyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, carbonyl having 1 to 10 carbon atoms, silyl having 3 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms; n represents the number of R, selected from an integer between 0 and 7; Any hydrogen in formula (a) may optionally be replaced by deuterium.

2. The triarylamine compound according to claim 1, characterized in that The triarylamine compound is selected from any one of formula (a1) or (a2): Wherein, Ar1, Ar2, L, L1, L2, R, and n have the same meanings as in claim 1.

3. The triarylamine compound according to claim 1, characterized in that The triarylamine compound is selected from any one of the following structures: Wherein, R1 to R8, Ar1, Ar2, L, L1, L2, R, and n have the same meanings as in claim 1.

4. The triarylamine compound according to claim 1, characterized in that The triarylamine compound is selected from any one of the following structures: Among them, R a is selected from deuterium, cyano, fluorine, trifluoromethyl, deuterated methyl, a linear or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an adamantyl group, or a substituted or unsubstituted group of the following: phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl; R b A straight chain or branched chain alkyl group having 1 to 6 carbon atoms, a deuterated methyl group, a cycloalkyl group having 3 to 6 carbon atoms, an adamantyl group, or a substituted or unsubstituted group selected from the following groups: phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl; n is selected from an integer between 0 and 7; m is selected from an integer between 0 and 6; R1 to R8, Ar1, Ar2, L, L1, and L2 have the same meanings as in claim 1.

5. The triarylamine compound according to claim 1, characterized in that: L, L1, L2 are each independently selected from a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms; alternatively, L, L1, L2 are each independently selected from a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms; further alternatively, L, L1, L2 are each independently selected from a substituted or unsubstituted arylene group having 6 to 16 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 16 carbon atoms.

6. The triarylamine compound according to claim 1, characterized in that: L, L1, L2 are each independently selected from the following groups which are single bonds, substituted or unsubstituted: phenylene, biphenylene, naphthylene, phenanthrenylene, fluorenylene, dibenzothienylene, dibenzofuranylene.

7. The triarylamine compound according to claim 1, characterized in that: Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms; alternatively, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms; further alternatively, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 16 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 16 carbon atoms.

8. A triarylamine compound according to claim 1, characterized in that: Ar1 and Ar2 are each independently selected from the following substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, diphenylfluorenyl, spirofluorenyl, spirofluorenyl, carbazolyl, dibenzothiophenyl, dibenzofuranyl, benzofluorenyl, benzospirofluorenyl, benzocarbazolyl, benzonaphthothiophenyl, and benzonaphthofuranyl.

9. The triarylamine compound according to any one of claims 1, 4 to 8, characterized in that: The substituent in the "substituted or unsubstituted" is selected from deuterium, cyano, halogen group, trifluoromethyl, straight or branched alkyl group with 1 to 6 carbon atoms, cycloalkyl group with 3 to 10 carbon atoms, aryl group with 6 to 20 carbon atoms, and heteroaryl group with 3 to 20 carbon atoms; Optionally, any hydrogen atom in the aforementioned substituents may be replaced by deuterium.

10. The triarylamine compound according to claim 9, characterized in that: The substituents in the "substituted or unsubstituted" are selected from deuterium, cyano, halogen groups, trifluoromethyl, straight-chain or branched alkyl groups having 1 to 6 carbon atoms, cycloalkyl groups having 3 to 6 carbon atoms, adamantyl, phenyl, naphthyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzothienyl, and dibenzofuranyl; optionally, any hydrogen atom in the aforementioned substituents may be substituted by deuterium.

11. The triarylamine compound according to claim 1, characterized in that: The triarylamine compound is selected from any one of the following compounds: 12 . A functional layer comprising the triarylamine compound according to claim 1 .

13. Use of the triarylamine compound according to any one of claims 1 to 11 and / or the functional layer according to claim 12 in an organic electroluminescent device.

14. An organic electroluminescent device comprising a first electrode, a second electrode and the functional layer according to claim 12, wherein: The functional layer is at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron injection layer or an electron transport layer.

15. A display or lighting device comprising the organic electroluminescent device according to claim 14.

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