Triarylamine compound for organic electroluminescent device, application of triarylamine compound and organic electroluminescent device

Abstract

The invention provides a novel prime material and a compound used for an organic electroluminescence device, the novel prime material is characterized by comprising a compound with a structure represented by a formula (I), # imgabs0 #, the compound can be used for positions such as an electron blocking layer in an organic EL device, the preparation is simple, the transmission of carriers in the device can be improved and balanced, the voltage of the device can be reduced, and the performance of the device can be improved. The luminous efficiency is improved; and the service life is prolonged.

Description

Technical Field

[0001] The invention relates to the technical field of organic electroluminescence, in particular to a compound used for an organic electroluminescent device, and also to an organic electroluminescent device. Background Art

[0002] In recent years, optoelectronic devices based on organic materials have become increasingly popular. The inherent flexibility of organic materials makes them very suitable for manufacturing on flexible substrates. Beautiful and cool optoelectronic products can be designed and produced according to demand, gaining unparalleled advantages over inorganic materials. Examples of such organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, organic sensors, etc. Among them, OLED has developed particularly rapidly and has achieved commercial success in the field of information display. OLED can provide highly saturated red, green, and blue colors. Full-color display devices made of OLEDs do not require additional backlight sources and have the advantages of brilliant colors, lightness, thinness, and softness.

[0003] The core of OLED devices is a thin film structure containing a variety of organic functional materials. Common functionalized organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, luminescent host materials and luminescent guest (dyes), etc. When power is turned on, electrons and holes are injected and transported to the luminescent area respectively and recombine there, thereby generating excitons and emitting light.

[0004] People have developed a variety of organic materials, combined with various unique device structures, which can improve carrier mobility, regulate carrier balance, break through electroluminescence efficiency, and delay device attenuation. For quantum mechanical reasons, common fluorescent luminescent bodies mainly use singlet excitons generated when electrons and holes combine to emit light, and are still widely used in various OLED products. Some metal complexes, such as iridium complexes, can simultaneously use triplet excitons and singlet excitons to emit light, and are called phosphorescent luminescent bodies. Their energy conversion efficiency can be increased by up to four times that of traditional fluorescent luminescent bodies. Thermally excited delayed fluorescence (TADF) technology promotes the transformation of triplet excitons to singlet excitons. Without the use of metal complexes, triplet excitons can still be effectively utilized to achieve higher luminescence efficiency. Thermally excited sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize luminescent bodies by energy transfer, which can also achieve higher luminescence efficiency. As OLED products gradually enter the market, people have higher and higher requirements for the performance of such products. The currently used OLED materials and device structures cannot completely solve the problems of OLED product efficiency, life span, cost, etc. In recent years, people in the industry have been constantly trying and exploring to improve device efficiency and stability. Most of them are seeking new materials to improve device performance. A large number of novel materials have been developed for use in organic electroluminescent devices. Although they have improved device performance to a certain extent, there is still a large amount of carrier accumulation at the interface, and there is also the problem of low device efficiency.

[0005] Electron blocking materials have a significant impact on the performance of devices. On the one hand, hole transport materials need to have a suitable HOMO energy level. The appropriate energy gap between the hole material and the anode is conducive to the injection of holes and can help reduce the operating voltage. On the other hand, hole transport materials regulate the transport balance of carriers in the device and improve the carrier mobility of hole transport materials, thereby improving luminous efficiency and delaying device attenuation. Although products using OLED display technology have been commercialized, there is still a demand for further improvement in device efficiency and service life.

[0006] Therefore, the field is in urgent need of developing more types of higher performance organic materials to improve the performance of organic electroluminescent devices so as to enable the devices to have higher luminous efficiency and lower driving voltage. Summary of the invention

[0007] In view of the shortcomings of the prior art, one of the purposes of the present invention is to provide a compound that can be used as an electron blocking layer material in an organic electronic device, and the electronic device using the compound has high luminous efficiency and low starting voltage, and the life span is greatly improved. To achieve this purpose, the inventors have devoted themselves to research and developed the following technical solutions to complete the present invention.

[0008] Specifically, the present invention provides a triarylamine compound, characterized in that it is a compound having a structure represented by formula (I):

[0009]

[0010] In formula (I), the M group is a group represented by formula (I-1), and ring A represents a biphenyl ring, a naphthyl ring, or a substituted or unsubstituted C3-C30 heteroaryl group; Ar 2 Located at the ortho position to the N substitution position on ring A;

[0011] L 1 , L 2 Each is independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group;

[0012] Ar 2 is a substituted or unsubstituted C10-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group;

[0013] Ar 1 One selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0014] R 1 , R 2 Each is independently a substituted or unsubstituted C1-C20 chain alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group;

[0015] R 3 , R 4 Each is independently hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; m is an integer selected from 0-7; n is an integer from 0 to the maximum allowed value;

[0016] Wherein, X is selected from O, S, NR 11 or CR 12 R 13 ; R 11 is selected from one of hydrogen, C1-C20 linear alkyl, C1-C20 linear halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl; R12 , R 13 Each is independently selected from one of hydrogen, C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, halogen, cyano, C6-C30 aryl, and C3-C30 heteroaryl;

[0017] The substituents in the above substituted or unsubstituted groups are independently selected from one or a combination of at least two of halogen, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl;

[0018] The expression of a ring structure with a “—” indicates that the connection site is any position on the ring structure that can form a bond, and the wavy line indicates the connection site.

[0019] When the compound of the present invention is used as an electron blocking material, it can effectively reduce the driving voltage of the device and improve the luminous efficiency of the device. According to the comparative test in the embodiment, it is believed that it also helps to improve the life characteristics. The reason is not clear, but it may be the following reasons:

[0020] The triarylamine compound itself has a strong hole transport ability and is suitable for electron blocking. Compared with other aromatic groups or substituted aromatic and heteroaryl groups, the introduction of heteroanthracene on the periphery of the molecule has a stronger internal force between molecular groups, a stronger spatial structural repulsion, a greater probability of σ-π hyperconjugation, and a shallower LUMO energy level, which is beneficial to prolong device life and reduce voltage. 2 The anthracene on the surface has a certain intramolecular field effect in the spatial structure, which increases the rigidity of the molecular structure under synergistic traction and also increases the delocalization range of electrons, thereby enhancing the electron blocking ability and increasing the current efficiency. 2 Compared with other aromatic or substituted aromatic groups and heteroaromatic groups, the introduction of heteroanthracene reduces the mutual repulsion effect between groups, enhances the stability of the molecular structure, is conducive to the formation of a stable amorphous film, and is beneficial to the stability of the device.

[0021] It should be noted that in this specification, the expression of Ca to Cb means that the number of carbon atoms in the group is a to b. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms in the substituent. For example, C1 to C10 represents C1, C2, C3, C4, C5, C6, C7, C8, C9, and C10, indicating that the intermediate numbers are also recorded in the present invention. In the present invention, the expression of chemical elements, unless otherwise specified, usually includes the concept of isotopes with the same chemical properties. For example, the expression of "hydrogen" also includes the concepts of "deuterium" and "tritium" with the same chemical properties, and carbon (C) includes 12 C. 13 C, etc., no further details.

[0022] In the structural formula disclosed in this specification, the expression of the ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond.

[0023] In this specification, unless otherwise specified, aryl and heteroaryl include both monocyclic and condensed rings. The so-called monocyclic aryl refers to a molecule containing at least one phenyl group. When the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, such as phenyl, biphenyl, terphenyl, etc.; condensed ring aryl refers to a molecule containing at least two benzene rings, but the benzene rings are not independent of each other, but condensed to each other by sharing the ring edge, such as naphthyl, anthracenyl, etc.; monocyclic heteroaryl refers to a molecule containing at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and other groups are independent of each other and connected by a single bond, such as pyridine, furan, thiophene, etc.; condensed ring heteroaryl refers to a molecule composed of at least one phenyl group and at least one heteroaryl group fused together, or at least two heteroaryl rings fused together, such as quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, etc.

[0024] In the present specification, the substituted or unsubstituted C6-C60 aromatic group is preferably a C6-C30 aromatic group, and more preferably a group selected from the group consisting of phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrene, chrysene, peryl, fluoranthene, naphthyl, pentacene, benzopyrene, biphenyl, isophenyl, terphenyl, triphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, and spiroisotrimerized indenyl. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetraphenyl group is selected from 1-tetraphenyl, 2-tetraphenyl and 9-tetraphenyl. Preferred examples of the aryl group in the present invention include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and its derivatives, fluoranthenyl, triphenylene, pyrenyl, peryl, The biphenyl group is selected from the group consisting of 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl or 2-naphthyl; the anthracenyl group is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl. The fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9,9-dimethylfluorene, 9,9-spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the naphthyl group is selected from the group consisting of 1-naphthyl, 2-naphthyl and 9-naphthyl. The C6-C60 aryl group of the present invention can also be a group formed by combining the above groups by single bond connection or / and fusion.

[0025] The heteroatom in the present invention is generally selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0026] In the present specification, the substituted or unsubstituted C3-C60 heteroaryl group is preferably a C3-C30 heteroaryl group, more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, etc. Specific examples include: furyl, thienyl, pyrrolyl, pyridyl, benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, isoindolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and its derivatives, quinolyl, isoquinolyl, acridinyl, phenanthridine yl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthroxazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidazinyl, pyridinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazolyl, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purinyl, pteridinyl, indolizine, benzothiadiazole and the like. Preferred examples of heteroaryl groups in the present invention include furanyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazolebenzocarbazole, dibenzocarbazole or indolecarbazole. The C3-C60 heteroaryl group of the present invention may also be a group formed by combining the above groups by single bond connection or / and fusion.

[0027] In this specification, the term alkyl includes the concept of cycloalkyl, and if the emphasis is on chain alkyl, cycloalkyl is not included. Examples of C1-C30 alkyl include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, adamantyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, etc. The C1-C30 alkyl is preferably a C1-C12 alkyl, more preferably a C1-C10 alkyl, and more preferably a C1-C6 alkyl.

[0028] In the present specification, the cycloalkyl group includes a monocyclic alkyl group and a polycyclic alkyl group, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.

[0029] In the present specification, examples of C1-C30 alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, etc., among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy, and methoxy is more preferred.

[0030] In the present specification, examples of C1-C30 silyl groups include silyl groups substituted with the groups listed in the above C1-C30 alkyl groups, specifically including methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and the like.

[0031] In the present specification, examples of halogen include fluorine, chlorine, bromine, iodine and the like.

[0032] More specifically, as the above-mentioned R group, preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, triphenylenyl, pyrenyl, chrysene, peryl, fluoranthenyl, naphthyl, pentacene, benzopyrenyl, biphenyl, phenylene, terphenyl, tripolyphenyl, quaternaryl, fluorenyl , spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis- or trans-indenofluorenyl, trimerized indenyl, isotrimerized indenyl, spirotrimerized indenyl, spiroisotrimerized indenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridinyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo-7,8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyrrolyl, imidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthrazolyl, phenanthrozolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthryl, 2,7-diazapyrenyl, 2,3-diazapyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1, 2,3-triazolyl, 1,2,4-triazolyl, benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, or a combination of the above two groups. But not limited to these groups.

[0033] In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or with multiple substituents. When there are multiple substituents, they may be selected from different substituents. When the same expressions are involved in the present invention, they all have the same meaning, and the selection range of substituents is as shown above and will not be repeated one by one.

[0034] In a preferred embodiment of the present invention, L 1 , L 2 is a single bond, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted phenylene, preferably, L 1 , L 2 Each is independently a phenylene group or a single bond, and the substituent here is selected from one or a combination of at least two of halogen, nitro, cyano, C6-C60 aryl, C3-C60 heteroaryl, C1-C20 straight or branched alkyl, C1-C10 alkoxy, C6-C30 aryloxy, amino, C1-C20 alkylsilyl, C6-C30 arylamino, and C3-C30 heteroarylamino.

[0035] In a preferred embodiment of the present invention, R is selected from substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C1-C10 chain alkoxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and the substituent is selected from one or a combination of two of halogen, carboxyl, nitro, cyano, amino, hydroxyl, and thiol.

[0036] In a preferred embodiment of the present invention, the M group is a structure represented by formula (a), formula (b) and formula (c),

[0037]

[0038] Ar 3 ~Ar 5 is a substituted or unsubstituted C10-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group, and n is an integer from 0 to the maximum permitted value; R 4 It is hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl. The expression of the ring structure with “—” crossed out indicates that the connection site is any position on the ring structure that can form a bond, and the wavy line indicates the connection site.

[0039] In a preferred embodiment of the present invention, Ar 3 ~Ar 5 are each independently a substituted or unsubstituted C10-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group; preferably, Ar 3 ~Ar 5 is the following substituted or unsubstituted groups:

[0040]

[0041] The substitution in the above “substituted or unsubstituted” refers to substitution with at least one selected from halogen, phenyl, cyano, methyl, cyclohexyl, cyclopentyl, and fluorenyl. The expression of the ring structure crossed out by “—” indicates that the connection site is any position on the ring structure that can form a bond, and the asterisk indicates the connection site.

[0042] In a preferred embodiment of the present invention, L 1 , L 2 is a substituted or unsubstituted one selected from the following groups,

[0043]

[0044] Y 1 Each independently selected from O, S, NR 21 or CR 22 R 23 ; R 21 is selected from one of hydrogen, C1-C20 linear alkyl, C1-C20 linear halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl; R 22 , R 23 are independently selected from one of hydrogen, C1-C20 chain alkyl, C1-C20 chain haloalkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, C6-C30 aryl, and C3-C30 heteroaryl; the expression of "—" crossing the ring structure indicates that the connection site is at any position on the ring structure that can form a bond, and the wavy line indicates the connection site. The substitution in the above "substituted or unsubstituted" refers to substitution by at least one selected from halogen, phenyl, cyano, methyl, cyclohexane, cyclopentane, and fluorenyl. Preferably, L 1 , L 2 Selected from a single bond or one of the following groups:

[0045]

[0046] In a preferred embodiment of the present invention, R 3 is selected from halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; m is an integer of 0 to 3, and each R 3 Same or different, adjacent R 3 Optionally fused or unfused;

[0047] R 4 Each is independently selected from halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, n is an integer of 0 to 3, each R 4 Same or different,

[0048] The substituents in the above-mentioned substituted or unsubstituted groups are independently selected from at least one or a combination of two or more of halogen, phenyl, cyano, methyl, isopropyl, tert-butyl, isobutyl, cyclohexyl, cyclopentyl, and fluorenyl; the expression of the ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond.

[0049] In a preferred embodiment of the present invention, X is O or S, preferably O,

[0050] R 1 , R 2 are each independently selected from H, methyl, ethyl, isopropyl, tert-butyl, phenyl, cyano, naphthyl, dibenzofuran, dibenzothiophene, methylfluorene and carbazole,

[0051] Preferably R 1 , R 2 Each is independently methyl, ethyl, propyl, phenyl, naphthyl; more preferably, R 1 , R 2 Each is independently a methyl group or a phenyl group.

[0052] In a preferred embodiment of the present invention, Ar 1 One selected from the following substituted or unsubstituted groups:

[0053]

[0054]

[0055]

[0056]

[0057]

[0058] The term "substituted or unsubstituted" as used herein means substituted by at least one selected from the group consisting of halogen, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl, cyano, methyl, ethyl, isopropyl, tert-butyl, isobutyl, dimethylpropyl, cyclohexyl and adamantane;

[0059] More preferably, Ar 1 Each is independently selected from one of the following groups:

[0060]

[0061] As specific examples of the compound represented by the formula (I), any one of the structures shown below can be cited, but it is not limited to these specific compounds:

[0062]

[0063]

[0064]

[0065]

[0066]

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[0069]

[0070]

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[0075]

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[0080]

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[0089]

[0090]

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[0100]

[0101] It should be noted that, for the sake of convenience, the possible effects of each group / feature are described separately in this application, but this does not mean that these groups / features act in isolation. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between the various groups, rather than the effect of a single group.

[0102] In summary, the compound is applied to organic electroluminescent devices, especially as an electron blocking layer material and / or a hole transport layer material, which can effectively improve the efficiency and stability of the device, prolong the life, reduce the voltage and energy consumption, and achieve a better luminous effect. In addition, the preparation process of the compound of the present invention is simple and easy, the raw materials are easily available, and it is suitable for mass production and expansion.

[0103] It should be noted that, in order to facilitate explanation, the possible effects of each group / feature are described separately in the present invention, but this does not mean that these groups / features act in isolation. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between the various groups, rather than the effect of a single group.

[0104] Another aspect of the present invention provides an organic electroluminescent device, comprising a first electrode, a second electrode and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer comprises the triarylamine compound of the present invention.

[0105] Another aspect of the present invention provides an electron blocking material for an organic electroluminescent device, which contains the compound described in the present invention.

[0106] Another aspect of the present invention provides the use of the compound of the present invention as a functional material in an organic electronic device, wherein the organic electronic device includes: an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner or an electronic paper.

[0107] The present invention also provides a display device, wherein the display device comprises the organic electroluminescent device.

[0108] In summary, the compounds provided by the present invention as electron blocking materials are conducive to obtaining the excellent effects of higher luminous efficiency and low starting voltage as well as improved life characteristics. The preparation process of the compounds of the present invention is simple and easy, the raw materials are readily available, suitable for mass production and amplification, and very suitable for industrial applications.

[0109] The OLED device prepared by using the compound of the present invention has low starting voltage, high luminous efficiency and better service life, and can meet the requirements of current panel and display manufacturers for high-performance materials.

[0110] The above-mentioned compound of the present invention has high hole affinity and hole transport properties, and can be used for electron blocking or hole injection in organic electronic devices (including but not limited to organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners or electronic paper).

[0111] The present invention also provides an organic electroluminescent device, which includes a first electrode, a second electrode and at least one or more light-emitting functional layers inserted between the first electrode and the second electrode, and the compound described in the present invention is used in at least one layer of the light-emitting functional layers.

[0112] The organic electroluminescent device of the present invention has a structure consistent with that of existing devices, for example, comprising an anode layer, multiple light-emitting functional layers and a cathode layer; the multiple light-emitting functional layers include a light-emitting layer and at least one layer selected from an electron blocking layer, an electron transport layer, and an electron injection layer, wherein at least one layer selected from a hole transport layer, a hole injection layer or an electron blocking layer contains the above-mentioned organic compound of the present invention.

[0113] The OLED device prepared by using the compound of the present invention has low starting voltage, high luminous efficiency and better service life, and can meet the requirements of current panel and display manufacturers for high-performance materials. DETAILED DESCRIPTION

[0114] The technical solution of the present invention is further described in more detail below. It should be understood by those skilled in the art that the embodiments are only used to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0115] Method for obtaining the compound of the present invention

[0116] The representative synthesis route of the compound of formula (I) of the present invention is as follows:

[0117]

[0118] Wherein, each symbol has the same meaning as in Formula I; X represents halogen, Pd2(dba)3 represents tris(dibenzylacetone)dipalladium(0), IPr.HCl represents 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride, t-BuONa represents sodium tert-butoxide, and (t-Bu)3P represents tri-tert-butylphosphine. More specifically, the following synthesis example of the present invention exemplarily provides a specific synthesis method of a representative compound, and the solvents and reagents used in the following synthesis example can all be purchased or customized from the domestic chemical product market. In addition, those skilled in the art can also synthesize by known methods.

[0119] Organic electroluminescent device of the present invention

[0120] Furthermore, the structure of the organic electroluminescent device of the present invention is a well-known structure, characterized in that the compound of the present invention is used in one or more layers of the electron blocking layer. According to the basic principle and usage habits, the compound of the present invention can also be used in the main layer, the hole transport layer, and the hole injection layer. The organic electroluminescent device is described in detail below.

[0121] In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a thin film transistor (TFT) may also be provided on the substrate used as a display.

[0122] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO) and any combination thereof can be used. When the first electrode is used as a cathode, a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and any combination thereof can be used.

[0123] The organic material layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic material layer can be organic small molecules, organic macromolecules and polymers, and combinations thereof.

[0124] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multilayer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light-emitting layer.

[0125] The material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives such as the compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0126]

[0127]

[0128]

[0129] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can use one or more compounds of HT-1 to HT-51 above, or one or more compounds of HI-1 to HI-3 below; or one or more compounds of HT-1 to HT-51 can be doped with one or more compounds of HI-1 to HI-3 below.

[0130]

[0131] The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a host material (Host). The light-emitting layer can be a monochrome light-emitting layer that emits a single color such as red, green, and blue. A plurality of monochrome light-emitting layers of different colors can be arranged in a plane according to a pixel pattern, or they can be stacked together to form a color light-emitting layer. When light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single color light-emitting layer that can simultaneously emit different colors such as red, green, and blue.

[0132] According to different technologies, the light-emitting layer material can be made of different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescent materials. In an OLED device, a single light-emitting technology can be used, or a combination of multiple different light-emitting technologies can be used. These different light-emitting materials classified by technology can emit light of the same color or different colors.

[0133] In one aspect of the present invention, the light-emitting layer adopts fluorescent electroluminescence technology. The fluorescent host material of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFH-1 to BFH-17 listed below.

[0134]

[0135] In one aspect of the present invention, the light-emitting layer adopts fluorescent electroluminescence technology. The fluorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFD-1 to BFD-24 listed below.

[0136]

[0137]

[0138]

[0139] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology, and the main material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-85.

[0140]

[0141]

[0142]

[0143]

[0144] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of GPD-1 to GPD-47 listed below.

[0145]

[0146]

[0147]

[0148] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of RPD-1 to RPD-28 listed below.

[0149]

[0150]

[0151] In one aspect of the present invention, the light-emitting layer adopts phosphorescent electroluminescence technology. The phosphorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of YPD-1 to YPD-11 listed below.

[0152]

[0153] In one aspect of the present invention, the light-emitting layer adopts the technology of thermally activated delayed fluorescence luminescence. The main material of the light-emitting layer is selected from, but not limited to, one or more combinations of the above PH-1 to PH-85.

[0154] In one aspect of the present invention, the light-emitting layer adopts the technology of thermally activated delayed fluorescence luminescence. The fluorescent dopant of the light-emitting layer can be selected from, but not limited to, one or more combinations of TDE1-TDE37 listed below.

[0155]

[0156]

[0157] In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be, but not limited to, one or more of the compounds HT-1 to HT-51 described above, or one or more of the compounds PH-47 to PH-77 described above; or a mixture of, but not limited to, one or more of the compounds HT-1 to HT-51 and one or more of the compounds PH-47 to PH-77.

[0158] The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may also be a multilayer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0159] In one aspect of the present invention, the electron transport layer material can be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0160]

[0161]

[0162]

[0163]

[0164] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may be, but not limited to, one or more compounds of ET-1 to ET-73, or one or more compounds of PH-1 to PH-46; or a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46.

[0165] The device may also include an electron injection layer located between the electron transport layer and the cathode. The electron injection layer material includes but is not limited to one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, and Yb.

[0166] Example

[0167] The organic compounds of the present invention were synthesized representatively, and applied together with corresponding comparative compounds in organic electroluminescent devices to test the device performance under the same conditions.

[0168] The present invention provides the specific synthesis method of representative compound by way of example as follows synthetic example, and the solvent and reagent used in the following synthetic example, intermediate, chemical reagents such as ethyl acetate, methanol, ethanol, etc., can all be purchased or customized from the domestic chemical product market. The mass spectrum characterization data in the following synthetic example are obtained by the ZAB-HS type mass spectrometer test manufactured by Micromass Company of Britain. Specifically, it is matrix-assisted laser desorption ionization time-of-flight mass spectrometry MALDI-TOF mass spectrometry, wherein the ion source is matrix-assisted laser desorption / ionization (Matrix-assisted laser desorption / ionization, MALDI), and the mass analyzer is time-of-flight (time of flight, TOF) analyzer.

[0169] Synthesis Example 1: Synthesis of Compound A3

[0170]

[0171] In a 2000mL single-mouth bottle, add 50g of Q, 36.26g of p-bromobiphenyl, 2.85g of Pd2(dba)3, 2.64g of IPr.HCl and 29.9g of sodium tert-butoxide, 1000mL of toluene, evacuate and replace with nitrogen 3 times, and heat to 90℃ for 10h. After the reaction is completed, stop the reaction, cool to room temperature, separate the reaction liquid, purify the organic phase twice with silica gel column, concentrate the organic phase, add methanol and reflux and stir for 1h, filter to obtain light yellow powder W, and then recrystallize from ethyl acetate to obtain 54.5g of pure product.

[0172] Organic compounds: W: m / z theoretical value: 473.21; m / z measured value: 474.28.

[0173] In a 1000mL single-mouth bottle, add 10g of W, 9.16g of 2-bromo-9,9-dimethyloxanthene, 0.39g of Pd2(dba)3, 0.17g of tri-tert-butylphosphine, 4.06g of sodium tert-butoxide, 300mL of toluene, evacuate and replace with nitrogen 3 times, heat to reflux, and react for 14 hours. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction solution, purify the organic phase twice with silica gel column, concentrate the organic phase, add methanol and reflux and stir for 1h, filter to obtain white powder A1, and then recrystallize three times from ethyl acetate to obtain 9.7g of pure product.

[0174] Organic compound A3: m / z theoretical value: 681.30; m / z measured value: 682.40.

[0175] Other Synthesis Examples

[0176] The process route is the same as that of Synthesis Example 1, except that the raw materials are different. For example, the raw materials, target products and result characterization data of the compounds shown in Table 1 are obtained by synthesis.

[0177] Table 1

[0178]

[0179]

[0180]

[0181]

[0182] Note:

[0183] Synthesis of A410-Q:

[0184]

[0185] Synthesis of A783-Q:

[0186]

[0187] Device Embodiment

[0188] Example 1

[0189] The preparation process of the organic electroluminescent device in this embodiment is as follows:

[0190] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone / ethanol, baked in a clean environment until the moisture was completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam on the surface; the above-mentioned glass substrate with an anode was placed in a vacuum chamber, evacuated to <1×10-5Pa, and 10nm of a mixture of compound HT-4:HI-3 (97 / 3, w / w) was vacuum-evaporated on the above-mentioned anode layer in sequence as a hole injection layer, and 60nm of compound HT-4 as a hole transport layer was vacuum-evaporated. layer, 60nm of the organic compound A3 provided in the present application as an electron blocking layer; 40nm of the compound PH-35:RPD-8 (97 / 3, w / w) binary mixture as a light-emitting layer; 5nm of ET-23 as a hole blocking layer, 25nm of the compound ET-46:ET-57 (50 / 50, w / w) mixture as an electron transport layer, 0.5nm of LiF as an electron injection layer, and 150nm of metal aluminum as a cathode; the total evaporation rate of all organic layers and LiF is controlled at 0.1nm / s, and the evaporation rate of the metal electrode is controlled at 1nm / s.

[0191] Example 2-16

[0192] The organic electroluminescent devices in these embodiments are different from those in Embodiment 1 only in that the electron blocking layer material organic compound A3 is replaced by A41, A50, A51, A59, A208, A209, A215, A410, A427, A487, A551, A568, A583, A783, A784.

[0193] Comparative Examples 1-5

[0194] The organic electroluminescent device in the comparative example is different from that in Example 1 only in that the electron blocking layer material organic compound A3 is replaced by B1 (CN114805323 A), B2 (KR20210155230A), B3 (KR20220062937A), B4 (KR20220032906A), and B5 (CN202110719948A).

[0195]

[0196] The organic electroluminescent devices provided in the above-mentioned Examples 1-16 and Comparative Examples 1-5 were subjected to the following performance tests: at the same brightness, the driving voltage and current efficiency of the organic electroluminescent devices were measured using a digital source meter and a brightness meter. Specifically, the voltage was increased at a rate of 0.1 V per second, and the brightness of the organic electroluminescent device was measured when it reached 3000 cd / m 2 The current density at 3000cd / m 2 At the same brightness, the current is kept constant and the brightness of the organic electroluminescent device is measured to drop to 2910cd / m 2 The LT97 life test value of comparative example B1 is recorded as 1, and the LT97 life of each device embodiment and other comparative examples are the ratios of their respective LT97 life test values ​​to the test value of comparative example B1 (relative life).

[0197] The test results are shown in Table 2:

[0198] Table 2

[0199]

[0200]

[0201] The above results show that the novel organic material of the present invention can be used in organic electroluminescent devices to effectively improve the current efficiency, the current efficiency reaches 24.0-25.3cd / A, reduce the operating voltage, the operating voltage reaches 3.4-4.1v, and the life span reaches 1.2-1.6 times that of the reference material, and is an electron blocking material with good performance. The following is a speculation on the mechanism of the excellent performance of the compound of the present invention:

[0202] Example A783 Comparative Example B1 Compared with N atom adjacent to Ar 2 Compared with the phenyl substitution in B1, the substitution with biphenyl adds a benzene ring, which extends the linearity of the molecule, is beneficial to the linear horizontal orientation of the film formed during the evaporation process, and improves the luminous efficiency; compared with B2, in embodiments A41 and A209, ring A is a biphenyl structure, while B2 is a benzene group with larger steric hindrance, which has stronger hole mobility, reduces voltage and improves efficiency; compared with B4, in embodiment A410, ring A is a biphenyl, while B4 is a phenyl group. The increase in molecular weight can increase the glass transition temperature of the molecule itself, which is beneficial to the thermal stability of the molecule in the device and increases the device life.

[0203] Compared with Example A784, B3 has ring A biphenyl, Ar 2 The introduction of naphthalene substitution can increase the molecular weight and extend the linearity of the molecule, and at the same time make the material have a hole transport property brought by a deeper HOMO energy level, reduce the operating voltage, and improve the efficiency and life of the device; compared with Example A3, the thermal stability of the anthracene in Comparative Example B5 is better than that of DBF, which greatly improves the life. At the same time, compared with other aromatic groups and substituents, the spatial structure repulsion of the anthracene is enhanced, the probability of σ-π hyperconjugation is greater, and the operating voltage can be reduced; the compound of the present application has a better spatial morphology, effectively avoids molecular stacking, and prolongs the life of the device.

[0204] The above experimental data show that the novel organic material of the present invention is an organic light-emitting functional material with good performance as an electron blocking material for an organic electroluminescent device and has broad application prospects.

[0205] The applicant declares that the present invention illustrates the detailed method of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned detailed method, that is, it does not mean that the present invention must rely on the above-mentioned detailed method to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of various raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A triarylamine compound, characterized in that It is a compound having a structure represented by formula (I): In formula (I), the M group is a group represented by formula (I-1), and ring A represents a biphenyl ring, a naphthyl ring, or a substituted or unsubstituted C3-C30 heteroaryl group; L 1 , L 2 Each is independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; Ar 2 Located at the ortho position of the N substitution position on ring A, Ar 2 is a substituted or unsubstituted C10-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; Ar 1 One selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; R 1 , R 2 Each is independently a substituted or unsubstituted C1-C20 chain alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; R 1 , R 2 They are not connected to form a ring; R 3 , R 4 Each is independently hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; m is an integer selected from 0-7; n is an integer from 0 to the maximum allowed value; when m is greater than 1, the adjacent R 3 They may be connected to form a ring or not; X is selected from O, S, NR 11 or CR 12 R 13 ; R 11 is selected from one of hydrogen, C1-C20 linear alkyl, C1-C20 linear halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl; R 12 , R 13 Each is independently selected from one of hydrogen, C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, halogen, cyano, C6-C30 aryl, and C3-C30 heteroaryl; The substituents in the above-mentioned substituted or unsubstituted groups are each independently selected from the group consisting of halogen, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl, or a combination of at least two of the following groups; the expression of a ring structure crossed out by "—" indicates that the connection site is at any bonding position on the ring structure, and the wavy line indicates the connection site.

2. The triarylamine compound according to claim 1, characterized in that The M group is a structure represented by formula (a), formula (b) or formula (c), Ar 3 ~Ar 5 is a substituted or unsubstituted C10-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group, and n is an integer from 0 to the maximum permitted value; R 4 It is hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; the expression of the ring structure crossed by "—" indicates that the connection site is any position on the ring structure that can form a bond, and the wavy line indicates the connection site.

3. The triarylamine compound according to claim 2, characterized in that Ar 3 ~Ar 5 are each independently a substituted or unsubstituted C10-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group; preferably, Ar 3 ~Ar 5 is the following substituted or unsubstituted groups: The term "substituted or unsubstituted" as used herein means substituted by at least one selected from the group consisting of halogen, phenyl, cyano, methyl, cyclohexyl, cyclopentyl, and fluorenyl. The expression of a ring structure with a "—" indicates that the connection site is any position on the ring structure that can form a bond, and the asterisk indicates the connection site.

4. The triarylamine compound according to claim 1, characterized in that L 1 , L 2 is substituted or unsubstituted and is selected from one of the following groups, Y 1 Each independently selected from O, S, NR 21 or CR 22 R 23 ; R 21 is selected from one of hydrogen, C1-C20 linear alkyl, C1-C20 linear halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl; R 22 , R 23 Each is independently selected from one of hydrogen, C1-C20 chain alkyl, C1-C20 chain halogenated alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, ester, amino, C6-C30 aryl, and C3-C30 heteroaryl; The expression of "—" crossing the ring structure indicates that the connection site is any position on the ring structure that can form a bond, and the wavy line indicates the connection site. The substitution in the above "substituted or unsubstituted" refers to substitution with at least one selected from halogen, phenyl, cyano, methyl, cyclohexane, cyclopentane, and fluorenyl. Preferably, L 1 , L 2 Selected from a single bond or one of the following groups:

5. The triarylamine compound according to claim 1, characterized in that R 3 is selected from halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; m is an integer of 0 to 3, and each R 3 Same or different, adjacent R 3 Optionally fused or unfused; R 4 Each is independently selected from halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, n is an integer of 0 to 3, each R 4 Same or different, The substituents in the above-mentioned substituted or unsubstituted groups are independently selected from at least one or a combination of two or more of halogen, phenyl, cyano, methyl, isopropyl, tert-butyl, isobutyl, cyclohexyl, cyclopentyl, and fluorenyl; the expression of a ring structure crossed by "—" indicates that the connection site is any position on the ring structure that can form a bond.

6. The triarylamine compound according to claim 1, characterized in that Ar 1 One selected from the following substituted or unsubstituted groups: The substitution in the above-mentioned "substituted or unsubstituted" refers to substitution by at least one selected from halogen, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl, cyano, methyl, ethyl, isopropyl, tert-butyl, isobutyl, dimethylpropyl, cyclohexane and adamantane.

7. The triarylamine compound according to claim 1, characterized in that X is O or S, preferably O, R 1 , R 2 Each is independently selected from H, methyl, ethyl, isopropyl, tert-butyl, phenyl, cyano, naphthyl, dibenzofuran, dibenzothiophene, methylfluorene and carbazole, preferably R 1 , R 2 Each is independently methyl, ethyl, propyl, phenyl, naphthyl; more preferably, R 1 , R 2 are each independently a methyl group or a phenyl group, Ar 1 Each is independently selected from one of the following groups:

8. The triarylamine compound according to claim 1, characterized in that The formula (I) has any one of the following structures:

9. An organic electroluminescent device comprising a first electrode, a second electrode and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer comprises the triarylamine compound according to any one of claims 1 to 9. 10 . An electron blocking material for an organic electroluminescent device, comprising the triarylamine compound according to claim 1 .

11. Use of the triarylamine compound according to any one of claims 1 to 8 as a functional material in an organic electronic device, wherein the organic electronic device comprises: Organic electroluminescent device, optical sensor, solar cell, lighting element, organic thin film transistor, organic field effect transistor, organic thin film solar cell, information tag, electronic artificial skin sheet, sheet-type scanner or electronic paper. 12 . The use according to claim 10 , which is used as an electron blocking layer material or a hole transport layer material.

13. A display device comprising the organic electroluminescent device according to claim 9.

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