Triarylamine organic compound and application thereof in organic photoelectric device

Abstract

The invention relates to the field of organic electroluminescent materials, in particular to a triarylamine organic compound and application of the triarylamine organic compound in an organic photoelectric device. The chemical structure of the triarylamine organic compound is as shown in a formula (a): # imgabs0 # (a), the compound disclosed by the invention is applied to a device, and on the basis of realizing lower voltage, better current efficiency and longer service life of an OLED (Organic Light Emitting Diode) device, lower device capacitance is further obtained, so that the requirements of the industry are met.

Description

Technical Field

[0001] The present invention relates to the field of organic electroluminescent materials, in particular to a triarylamine organic compound and its application in organic photoelectric devices. Background Art

[0002] OLED devices consist of two metal electrodes and organic semiconductor layers between them, which is equivalent to a flat capacitor. Capacitance (Constant) is one of the inherent properties of OLED devices. A higher capacitance value will cause more charge to be stored at both ends of the device electrodes when power is applied. When the voltage applied across the device suddenly changes from high to low, the charge stored in the device will be released, and its brightness will not be able to change from bright to dark in a short period of time, resulting in a "ghosting" phenomenon. This is not conducive to obtaining excellent device display effects, especially high refresh rate displays. Therefore, the industry is eager to obtain low-capacitance OLED devices. Summary of the Invention

[0003] In view of the above-mentioned shortcomings of the prior art, the object of the present invention is to provide a triarylamine organic compound and its application in an organic photoelectric device, so as to solve the problems in the prior art.

[0004] To achieve the above-mentioned and other related purposes, the present invention provides a triarylamine organic compound, wherein the chemical structure of the triarylamine organic compound is shown in formula (a):

[0005]

[0006] in,

[0007] One of A1 and A2 is selected from hydrogen, and the other is selected from the group described in formula (a-1):

[0008]

[0009] R3, R4 are each independently selected from hydrogen, deuterium, methyl or deuterated methyl; m is selected from 1 or 2;

[0010] R1 and R2 are the same or different and are each independently selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, 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; or R1 and R2 are bonded to form a ring through a single bond;

[0011] L0, L1, L2 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 3 to 30 carbon atoms;

[0012] Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and satisfy the following conditions: at least one of Ar1 or Ar2 is selected from a group consisting of formula (a-2) or formula (a-3):

[0013]

[0014] in,

[0015] R is selected from deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 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;

[0016] n is selected from an integer between 0 and 7;

[0017] X is selected from O or S;

[0018] * indicates the bonding site.

[0019] The second aspect of the present invention provides an organic layer comprising the triarylamine organic compound as described in the first aspect of the present invention.

[0020] A third aspect of the present invention provides use of the aforementioned triarylamine organic compound and / or organic layer in an organic photoelectric device.

[0021] A fourth aspect of the present invention provides an organic photoelectric device, comprising a first electrode, a second electrode and an organic layer as described above in the present invention, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer or an electron transport layer.

[0022] A fifth aspect of the present invention provides a display or lighting device, comprising the organic optoelectronic device as described above in the present invention.

[0023] Compared with the prior art, the present invention has the following beneficial effects:

[0024] The present invention further introduces a group composed of formula (a-2) or formula (a-3) with moderate electron-withdrawing property, such as 1-dibenzofuranyl, 1-dibenzothiophene, 4-dibenzofuranyl or 4-dibenzothiophene, as the auxiliary hole transport layer of the device. While maintaining good hole mobility of the molecules, it can achieve lower voltage, better current efficiency and device life of the OLED device, and further obtain lower device capacitance, thereby meeting the needs of the industry. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] Figure 1 Schematic diagram of the structure of the organic electroluminescent device in the green light device embodiment.

[0026] Figure 2 Schematic diagram of the structure of the organic electroluminescent device in the blue light device embodiment.

[0027] In the picture:

[0028] 101 Base

[0029] 102 first electrode

[0030] 103 hole injection layer

[0031] 104 hole transport layer

[0032] 105 electron blocking layer

[0033] 106 Luminescent Layer

[0034] 107 hole blocking layer

[0035] 108 Electron Transport Layer

[0036] 109 second electrode

[0037] 110 Covering DETAILED DESCRIPTION

[0038] The following describes in detail embodiments of the specifically disclosed triarylamine organic compounds and their applications in organic optoelectronic devices. Those skilled in the art will readily appreciate the other advantages and benefits of the present invention based on the disclosure herein. The present invention may also be implemented or applied through various other specific embodiments, and the details herein may be modified or altered based on different perspectives and applications without departing from the spirit of the present invention.

[0039] Before further describing the specific embodiments of the present invention, it should be understood that the scope of protection of the present invention is not limited to the specific specific embodiments described below; it should also be understood that the terms used in the examples of the present invention are for describing specific specific embodiments rather than for limiting the scope of protection of the present invention; in the present specification and claims, unless otherwise expressly stated herein, the singular forms "a", "an" and "the" include plural forms.

[0040] When the embodiments provide numerical ranges, it should be understood that, unless otherwise specified in the present invention, both endpoints of each numerical range and any numerical value between the two endpoints may be selected. Unless otherwise defined, all technical and scientific terms used in the present invention have the same meaning as those generally understood by those skilled in the art. In addition to the specific methods, equipment, and materials used in the embodiments, according to the understanding of the prior art by those skilled in the art and the description of the present invention, any methods, equipment, and materials of the prior art similar or equivalent to the methods, equipment, and materials described in the embodiments of the present invention may also be used to implement the present invention.

[0041] The present invention aims to obtain a low-capacitance OLED device, and the inventors have proposed the following concepts:

[0042] The concept is based on the following observation: when a forward bias is applied on both sides of the OLED device, charges begin to accumulate at the electrodes, and the device capacitance at this time is only related to the dielectric constant of each organic layer in the device. As the voltage gradually increases, carriers are gradually injected from the electrodes into the device, and after transport and migration through auxiliary layers (such as hole transport layers, electron transport layers, etc.), positive and negative charges recombine in the light-emitting layer to form high-energy excitons, and release photons in the process of energy falling back to the ground state to achieve luminescence. In this process, as positive and negative charges are continuously injected, the distance between them decreases until a large number of excitons begin to form in the device, and the positive and negative charges are continuously consumed. Therefore, as the voltage increases, the overall device capacitance shows a process of first increasing and then decreasing.

[0043] In view of the above observations, the inventors believe that, from the perspective of molecular structure, in order to obtain lower device capacitance, the auxiliary layer needs to have faster carrier transport characteristics and at the same time not have strong charge storage capacity. For hole transport materials, on the one hand, it is necessary to have faster hole mobility, and on the other hand, groups with certain electron-withdrawing properties should be introduced so that the molecules give out holes as quickly as possible in the ionic state, and it is not easy to form charge storage. However, the selection of electron-withdrawing groups should be cautious. If the electron-withdrawing ability of the group is too strong, it will lead to an unstable ionic state, which is not conducive to improving the life of the device. Among them, hole transport layer materials are a class of materials, including hole injection layer materials, hole transport layer materials, electron blocking layer materials, etc.

[0044] Based on the above conclusions, the present invention further introduces 1-dibenzofuranyl, 1-dibenzothiophene, 4-dibenzofuranyl or 4-dibenzothiophene with moderate electron-withdrawing properties as the auxiliary hole transport layer of the device. While maintaining good hole mobility of the molecules, it can achieve lower voltage, better current efficiency and device life of the OLED device, and further obtain lower device capacitance, thereby meeting the needs of the industry.

[0045] Examples of the substituents in the present invention are described below, but the substituents are not limited thereto:

[0046] [Substituted or unsubstituted] Unless otherwise specifically indicated, it refers to being substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, and a heteroaryl group, an acenaphthenyl group, and a triarylamine organic compound group, or being unsubstituted; or being substituted with a substituent connecting two or more of the substituents exemplified above, or being unsubstituted. For example, a "substituent connecting two or more substituents" may include a biphenyl group, i.e., a biphenyl group may be an aryl group, or a substituent connecting two phenyl groups.

[0047] [Alkyl] can be straight chain or branched, and the number of carbon atoms is not particularly limited. In some embodiments, alkyl includes but is not limited to methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl.

[0048] The above description of the alkyl group also applies to the alkyl group in the aralkyl group, aralkylamino group, alkylaryl group and alkylamino group.

[0049] [Alkoxy] can be a straight or branched alkyl group containing an oxygen atom, and the number of carbon atoms is not particularly limited. Alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, and the like.

[0050] [Cycloalkyl] may be cyclic, and the number of carbon atoms is not particularly limited. In some embodiments, cycloalkyl includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like.

[0051] [Aryl] There are no particular limitations and the aryl group may be a monocyclic aryl group or a polycyclic aryl group. In some embodiments, monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, quaterphenyl, pentphenyl, and the like. Polycyclic aryl groups include, but are not limited to, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluorenyl, and the like. The fluorenyl group may be substituted, for example, 9,9'-dimethylfluorenyl, 9,9'-dibenzofluorenyl, and the like. In addition, two of the substituents may be combined to form a spirocyclic structure, for example, 9,9'-spirobifluorenyl, and the like.

[0052] The above description of the aryl group applies to the arylene group, except that the arylene group is divalent.

[0053] The above description of the aryl group can be applied to the aryl group in the aryloxy group, arylthio group, arylsulfonyl group, arylphosphino group, arylalkyl group, arylalkylamino group, arylalkenyl group, alkylaryl group, arylamino group and arylheteroarylamino group.

[0054] [Heteroaryl] contains one or more of N, O, P, S, Si and Se as heteroatoms. Heteroaryl includes, but is not limited to, pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, pyrazinyl, azinyl, thiazinyl, dioxinyl, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl, naphthyridinyl, triazaindenyl, indolyl, dihydroindole, indolizinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopy ... Pyrazinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothiophenyl, benzofuranyl, dibenzothiophenyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indenocarbazolyl, phenazinyl, imidazopyridinyl, phenazinyl, phenanthridinyl, phenanthrolinyl, phenothiazinyl, imidazopyridinyl, imidazophenanthridinyl, benzimidazoquinazolinyl, benzimidazophenanthridinyl, spiro[fluorene-9,9'-xanthene], benzobinaphthyl, dinaphthofuranyl, naphthylbenzofuranyl, dinaphthothienyl, naphthylbenzothienyl, triphenylphosphine oxide, triphenylborane, etc.

[0055] The above description of the heteroaryl group can be applied to the heteroaryl group in the heteroarylamine group and the arylheteroarylamine group.

[0056] The above description of heteroaryl groups applies to heteroarylene groups, except that the heteroarylene group is divalent.

[0057] In the present application, the term "halogen group" includes F, Cl, Br and I.

[0058] In the present application, the term "bonded ring" means a substituted or unsubstituted (3 to 30-membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or a combination thereof, preferably a substituted or unsubstituted (3 to 26-membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or a combination thereof, formed by connecting or fusing two or more adjacent substituents. In addition, the formed ring may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si and P, preferably at least one heteroatom selected from the group consisting of N, O and S. According to one embodiment of the present application, the number of atoms in the ring skeleton is 5 to 20; according to another embodiment of the present application, the number of atoms in the ring skeleton is 5 to 15. The connected or fused rings may be, for example, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted carbazole ring, etc.

[0059] In addition, the term "substituted" in the expression "substituted or unsubstituted" means that the hydrogen atom in a certain functional group is replaced by another atom or functional group (i.e., a substituent). Preferably, in the present application, the substituents substituted include, but are not limited to, each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. For example, deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, or a tert-butylphenyl group. Examples of alkyl groups having 1 to 6 carbon atoms 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, and n-hexyl. Examples of cycloalkyl groups having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl. Cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl are cycloalkyl groups having a single ring structure, while adamantyl is a cycloalkyl group having multiple ring structures.

[0060] Triarylamine organic compounds

[0061] In one aspect, the present invention provides a triarylamine organic compound, the chemical structure of which is shown in formula (a):

[0062]

[0063] in,

[0064] One of A1 and A2 is selected from hydrogen, and the other is selected from the group described in formula (a-1):

[0065]

[0066] * indicates the bonding site.

[0067] In formula (a-1) of the present invention, R3 and R4 are each independently selected from hydrogen, deuterium, methyl or deuterated methyl.

[0068] In formula (a-1) of the present invention, R3 and R4 are each independently selected from hydrogen.

[0069] In formula (a-1) of the present invention, R3 and R4 are each independently selected from deuterium.

[0070] In formula (a-1) of the present invention, R3 and R4 are each independently selected from a methyl group.

[0071] In formula (a-1) of the present invention, R3 and R4 are each independently selected from a deuterated methyl group.

[0072] In the formula (a-1) of the present invention, m is selected from 1 or 2.

[0073] Optionally, formula a-1 is selected from any one of the groups shown below:

[0074]

[0075] In formula (a) of the present invention, R1 and R2 are the same or different and are each independently selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, 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; or R1 and R2 are bonded to form a ring. Wherein, the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. Alternatively, for example, the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group. Further alternatively, in the substituent in the "substituted" group, the halogen group may be, for example, F, Cl, Br, etc. The alkyl group having 1 to 6 carbon atoms may be, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, and an n-hexyl group. The cycloalkyl group having 3 to 10 carbon atoms may be, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and an adamantyl group.

[0076] In formula (a) of the present invention, optionally, R1 and R2 are the same or different and are each independently selected from a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms; or R1 and R2 are bonded to form a ring. Wherein, the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. Alternatively, for example, the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group. Further alternatively, in the substituent in the "substituted" group, the halogen group may be, for example, F, Cl, Br, etc. The alkyl group having 1 to 6 carbon atoms may be, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, and an n-hexyl group. The cycloalkyl group having 3 to 10 carbon atoms may be, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0077] In formula (a) of the present invention, further optionally, R1 and R2 are the same or different from each other and are each independently selected from a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms; or R1 and R2 are bonded to form a ring through a single bond. Wherein, the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. Alternatively, for example, the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group. Further alternatively, in the substituent in the "substituted" group, the halogen group may be, for example, F, Cl, Br, etc. The alkyl group having 1 to 6 carbon atoms may be, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, and an n-hexyl group. The cycloalkyl group having 3 to 10 carbon atoms may be, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and an adamantyl group.

[0078] In formula (a) of the present invention, R1, R2 are each independently selected from a deuterated alkyl group having 1 to 4 carbon atoms, a deuterated cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or R1, R2 are bonded to each other through a single bond to form a substituted or unsubstituted cycloalkyl or spirofluorenyl group. Alternatively, for example, the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group. Further optionally, in the "substituted" substituent, the halogen group can be, for example, F, Cl, Br, etc. Examples of the alkyl group having 1 to 6 carbon atoms 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, and n-hexyl. Examples of the cycloalkyl group having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0079] In formula (a) of the present invention, preferably, R1 and R2 are each independently selected from methyl, perdeuterated methyl, phenyl, or perdeuterated phenyl; or R1 and R2 are bonded to each other via a single bond to form a cyclohexyl, cyclopentyl, or spirofluorenyl. Spirofluorenyl groups include spiro[cyclopentane-1,9'-fluorenyl, spiro[cyclohexane-1,9'-fluorenyl, spirobifluorenyl, and the like.

[0080] In the present invention, when R1 and R2 are benzene or methyl, any deuterated situation is within the scope of protection of the present invention (specifically, any part of R1-R4, A1-A2, Ar1-Ar2, L0-L2, fluorene, and benzocycloalkyl can be deuterated).

[0081] In formula (a) of the present invention, L0, L1, and L2 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 3 to 30 carbon atoms. The substituent in the "substituted or unsubstituted" group is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. For example, the substituent in the "substituted or unsubstituted" group is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group. Further optionally, in the "substituted" substituent, a halogen group may be, for example, F, Cl, Br, etc. An alkyl group having 1 to 6 carbon atoms may be, 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, or n-hexyl. A cycloalkyl group having 3 to 10 carbon atoms may be, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or adamantyl.

[0082] In formula (a) of the present invention, L0 is selected from a single bond, 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; wherein the substituent in the "substituted or unsubstituted" group is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. For example, the substituent in the "substituted or unsubstituted" group is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, or a tert-butylphenyl group. Further optionally, in the "substituted" substituent, the halogen group may be, for example, F, Cl, Br, etc. Examples of the alkyl group having 1 to 6 carbon atoms 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, and n-hexyl. Examples of the cycloalkyl group having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0083] In formula (a) of the present invention, L0 is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms. The substituents in the "substituted or unsubstituted" group are selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. For example, the substituents in the "substituted or unsubstituted" group are selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, or a tert-butylphenyl group. Further optionally, in the "substituted" substituent, the halogen group may be, for example, F, Cl, Br, or the like. Examples of the alkyl group having 1 to 6 carbon atoms 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, and n-hexyl. Examples of the cycloalkyl group having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0084] In formula (a) of the present invention, L0 is selected from a single bond, or a substituted or unsubstituted group: phenylene, biphenylene, fluorenylene, dibenzofuranylene, dibenzothiophenylene. Wherein, the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. For example, the substituent in the "substituted or unsubstituted" is deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, or a tert-butylphenyl group. Further optionally, in the "substituted" substituent, the halogen group may be, for example, F, Cl, Br, etc. Examples of the alkyl group having 1 to 6 carbon atoms 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, and n-hexyl. Examples of the cycloalkyl group having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0085] In the present invention, formula (a) is selected from any one of the following groups:

[0086]

[0087] In the present invention, L1 and L2 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 3 to 30 carbon atoms. The substituents in the "substituted or unsubstituted" group are selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. For example, the substituents in the "substituted or unsubstituted" group are selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, or a tert-butylphenyl group. Furthermore, in the "substituted" substituent, the halogen group may be, for example, F, Cl, Br, or the like. Examples of the alkyl group having 1 to 6 carbon atoms 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, and n-hexyl. Examples of the cycloalkyl group having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0088] In the present invention, L1 and L2 are each independently selected from a single bond, 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. The substituents in the "substituted or unsubstituted" group are selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. For example, the substituents in the "substituted or unsubstituted" group are selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, or a tert-butylphenyl group. Furthermore, in the "substituted" substituent, the halogen group may be, for example, F, Cl, Br, or the like. Examples of the alkyl group having 1 to 6 carbon atoms 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, and n-hexyl. Examples of the cycloalkyl group having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0089] In the present invention, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 15 carbon atoms. The substituents in the "substituted or unsubstituted" group are selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. For example, the substituents in the "substituted or unsubstituted" group are selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, or a tert-butylphenyl group. Furthermore, in the "substituted" substituent, the halogen group may be, for example, F, Cl, Br, or the like. Examples of the alkyl group having 1 to 6 carbon atoms 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, and n-hexyl. Examples of the cycloalkyl group having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0090] In the present invention, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms. The substituents in the "substituted or unsubstituted" group are selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. For example, the substituents in the "substituted or unsubstituted" group are selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, or a tert-butylphenyl group. Furthermore, in the "substituted" substituent, the halogen group may be, for example, F, Cl, Br, or the like. Examples of the alkyl group having 1 to 6 carbon atoms 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, and n-hexyl. Examples of the cycloalkyl group having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0091] In the present invention, L1 and L2 are each independently selected from a single bond, or a substituted or unsubstituted group: phenylene, biphenylene, fluorenylene, dibenzofuranylene, dibenzothiophenylene. Wherein, the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group. Further optionally, in the "substituted" substituent, the halogen group can be, for example, F, Cl, Br, etc. Examples of the alkyl group having 1 to 6 carbon atoms 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, and n-hexyl. Examples of the cycloalkyl group having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0092] In the present invention, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and satisfy the following conditions: at least one of Ar1 or Ar2 is selected from a group consisting of formula (a-2) or formula (a-3):

[0093]

[0094] * indicates the bonding site.

[0095] In the present invention, 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, and satisfy the condition that at least one of Ar1 or Ar2 is selected from a group consisting of formula (a-2) or formula (a-3). The substituents in the "substituted or unsubstituted" group are selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. For example, the substituents in the "substituted or unsubstituted" group are selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group. Further optionally, in the "substituted" substituent, a halogen group may be, for example, F, Cl, Br, etc. An alkyl group having 1 to 6 carbon atoms may be, 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, or n-hexyl. A cycloalkyl group having 3 to 10 carbon atoms may be, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or adamantyl.

[0096] In the present invention, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms, and satisfy the condition that at least one of Ar1 or Ar2 is selected from a group consisting of formula (a-2) or formula (a-3). Wherein, the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group. Further optionally, in the "substituted" substituent, a halogen group may be, for example, F, Cl, Br, etc. An alkyl group having 1 to 6 carbon atoms may be, 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, or n-hexyl. A cycloalkyl group having 3 to 10 carbon atoms may be, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or adamantyl.

[0097] In the present invention, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and satisfy the condition that at least one of Ar1 or Ar2 is selected from a group consisting of formula (a-2) or formula (a-3). The substituents in the "substituted or unsubstituted" group are selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. For example, the substituents in the "substituted or unsubstituted" group are selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group. Further optionally, in the "substituted" substituent, a halogen group may be, for example, F, Cl, Br, etc. An alkyl group having 1 to 6 carbon atoms may be, 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, or n-hexyl. A cycloalkyl group having 3 to 10 carbon atoms may be, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or adamantyl.

[0098] In the present invention, Ar1 and Ar2 are each independently selected from the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, fluorenyl, spirofluorenyl, spirofluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl. Wherein, the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group. Further optionally, in the substituent in the "substituted" group, the halogen group may be, for example, F, Cl, Br, etc. The alkyl group having 1 to 6 carbon atoms may be, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, and an n-hexyl group. The cycloalkyl group having 3 to 10 carbon atoms may be, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and an adamantyl group.

[0099] In formulas (a-2) and (a-3) of the present invention, R is selected from deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 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. The substituent in the "substituted or unsubstituted" group is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group. Further optionally, in the substituent in the "substituted" group, the halogen group may be, for example, F, Cl, Br, etc. The alkyl group having 1 to 6 carbon atoms may be, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, and an n-hexyl group. The cycloalkyl group having 3 to 10 carbon atoms may be, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and an adamantyl group.

[0100] In formulas (a-2) and (a-3) of the present invention, R is selected from deuterium, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted cycloalkyl group having 2 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms. The substituent in the "substituted or unsubstituted" group is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. For example, the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group. Further optionally, in the substituent in the "substituted" group, the halogen group may be, for example, F, Cl, Br, etc. The alkyl group having 1 to 6 carbon atoms may be, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, and an n-hexyl group. The cycloalkyl group having 3 to 10 carbon atoms may be, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and an adamantyl group.

[0101] In formulas (a-2) and (a-3) of the present invention, R is selected from deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, 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 substituent in the "substituted or unsubstituted" group is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. For example, deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group. Further optionally, in the "substituted" substituent, a halogen group may be, for example, F, Cl, Br, etc. An alkyl group having 1 to 6 carbon atoms may be, 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, or n-hexyl. A cycloalkyl group having 3 to 10 carbon atoms may be, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or adamantyl.

[0102] In formulas (a-2) and (a-3) of the present invention, R is selected from deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a phenyl group, a biphenyl group, a methylphenyl group, and a tert-butylphenyl group. Examples of the alkyl group having 1 to 10 carbon atoms 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, and n-hexyl. Examples of the cycloalkyl group having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0103] In the present invention, n represents the number of R, and n is selected from integers between 0 and 7, such as 0, 1, 2, 3, 4, 5, 6, and 7.

[0104] In the present invention, X is selected from O or S.

[0105] In a specific embodiment of the present invention, the triarylamine organic compound is selected from any one of the following chemical structures:

[0106]

[0107]

[0108]

[0109] 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 layer 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, and a light-emitting layer main material. More preferably, it is an electron blocking layer material.

[0110] In some specific embodiments, the structure of the organic electroluminescent device can be selected from one of the following:

[0111] (1) An organic electroluminescent device includes 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, i.e., 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.

[0112] (2) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode.

[0113] (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.

[0114] (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.

[0115] (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.

[0116] (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.

[0117] (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.

[0118] (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.

[0119] (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.

[0120] (10) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode.

[0121] (11) Anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode.

[0122] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode.

[0123] (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 embodiment of the present application).

[0124] 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 the cathode side, it is necessary to add a covering layer on the cathode side. The specific structure is as follows:

[0125] 1) Anode / hole injection layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode / covering layer.

[0126] 2) Anode / hole injection layer / second hole transport layer / first hole transport layer / light-emitting layer / first electron transport layer / cathode / covering layer.

[0127] 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.

[0128] 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.

[0129] 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.

[0130] 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.

[0131] 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.

[0132] 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.

[0133] 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.

[0134] 10) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode / covering layer.

[0135] 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.

[0136] 12) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode / covering layer.

[0137] 13) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / cathode / covering layer.

[0138] Some specific functional layers in the organic electroluminescent device will be described below.

[0139] Substrate:

[0140] The substrate is generally located below the anode and can be made of plastic or glass, and can be rigid or bendable. A driving unit is provided on the substrate to drive the corresponding pixel to emit light.

[0141] anode:

[0142] Organic EL (Organic Electro-Luminescence) components typically require the anode to have good conductivity, a flat surface, and be resistant to cracks. They also have certain requirements for the work function, primarily to ensure that it matches the hole injection layer and maximizes the hole injection effect.

[0143] When top emission is used (light emitting from the cathode side), the anode uses 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 below the anode (near 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 with other metals. The reflective electrode has a high reflectivity, which is required to be above 90%. The thickness is usually used in the range of 100nm to 500nm, preferably in the range of 80nm to 150nm.

[0144] When using a bottom emission method (light emitting from the cathode substrate side), the anode is made of a metal compound with a work function of 4.2 eV or higher, such as indium tin oxide alloy, tin oxide, indium zinc oxide, gold, silver, platinum, copper, carbon nanotubes, carbon nanowires, graphene, etc. The thickness is 10 nm to 1 μm, preferably 50 nm to 200 nm.

[0145] The anode can be produced by forming an electrode material into a thin film by a method such as vapor deposition, sputtering, or coating.

[0146] Hole injection layer:

[0147] The thickness of the hole injection layer is generally 3nm to 20nm. The hole injection layer uses a mixture of P-type material and hole transport material. The purpose of using P-type material is to accept holes from the anode and transfer them to the hole transport material. The weight proportion of P-type material 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 exceed 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 exceed 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 exceed 1eV.

[0148] The P-type material can be a metal oxide, such as molybdenum oxide, vanadium oxide, tungsten oxide, etc.; it can also be an organic material, such as 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-trimethylenetris(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 used in combination with the P-type material can be selected from the material of the second hole transport layer and can be the same as or different from the material of the second hole transport layer.

[0149] Second hole transport layer:

[0150] The second hole transport layer is typically 40nm to 150nm thick and typically uses compounds containing aromatic amines, either monoamines or polyamines. The hole transport material must have high hole mobility, reduce driving voltage, and a glass transition temperature exceeding 100°C to avoid crystallization at high temperatures.

[0151] First hole transport layer:

[0152] 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. Generally, 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:

[0153]

[0154] where n i ,d i They respectively indicate the refractive index coefficient 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; θ1 and θ2 represent the phase shift of light at the anode interface and the cathode interface, respectively.

[0155] 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, when red light is present, 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. When green light is present, 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. When blue light is present, 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".

[0156] Electron blocking layer:

[0157] 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 excitons generated in the light-emitting layer in the light-emitting layer, thereby improving the luminous efficiency of the device.

[0158] Luminous layer:

[0159] The materials of the light-emitting layer generally include 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%.

[0160] The guest dopant material used as the luminescent material may include a phosphorescent or fluorescent material or a thermally activated delayed fluorescent material. Red, green, and blue light can be selected from the above three types of guest dopant materials. For example, the guest dopant material for the luminescent layer corresponding to the red luminescent unit and the luminescent layer corresponding to the green luminescent unit is a phosphorescent material, while the guest dopant material for the luminescent layer corresponding to the blue luminescent unit is a fluorescent material.

[0161] Or for example, the guest doping material of the light-emitting layer corresponding to the light-emitting unit with red light emission color and the light-emitting layer corresponding to the light-emitting unit with green light emission color is a phosphorescent material, and the guest doping material of the light-emitting layer corresponding to the light-emitting unit with blue light emission color is a phosphorescent material.

[0162] 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.

[0163] 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.

[0164] 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 luminescence performance. Taking the top-emitting device as an example, the red light-emitting unit can be selected to have a luminous brightness of 1000 cd / m 2 The current efficiency is greater than 30cd / A, and the luminous unit with green luminous color has a luminous brightness of 6000cd / m 2 The current efficiency is greater than 100cd / A, and the light-emitting unit with a 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 luminous color of the luminescent unit is phosphorescent blue and the luminous brightness is 1000cd / m 2 The current efficiency is greater than 10cd / A. When the current efficiency is higher, the power consumption can be reduced.

[0165] As the light-emitting host material, one light-emitting host material or two light-emitting host materials can be selected.

[0166] Hole blocking layer:

[0167] To enhance the balance between hole and electron concentrations, a hole-blocking layer is inserted to balance carrier concentrations and prevent exciton quenching. Typically, the hole-blocking layer is located between the light-emitting layer and the electron-transporting layer. The hole-blocking layer material must meet requirements such as high stability, good film-forming properties, and a high maximum molecular orbital.

[0168] First electron transport layer:

[0169] 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. When there is no second electron transport layer, the thickness of the first electron transport layer is generally 20nm to 50nm. When a second electron transport layer is present, 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. Therefore, similar to the first hole transport layer, it will also undergo electronic changes during the electron transport process, resulting in increased molecular vibration and molecular deformation. The excitons of the light-emitting layer will also interact with the polarons of the electron transport material. This interaction can easily generate active free radicals that 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 an organic electron transport material and a metal compound, or a mixture of an organic electron transport material and a metal.

[0170] When the organic electron transport material is mixed with a metal compound material, for example, with an alkali metal compound, an alkaline earth metal compound, or a rare earth metal compound, more specifically, with a lithium metal compound, a calcium metal compound, a magnesium metal compound, a samarium metal compound, or a ytterbium metal compound, and more specifically, with lithium 8-hydroxyquinoline, lithium fluoride, magnesium fluoride, ytterbium fluoride, or calcium fluoride. When mixed with the metal compound, the weight proportion of the organic electron transport material can be 20% to 80%, 20% to 40%, 40% to 60%, or 60% to 80%.

[0171] When the organic electron transport material is mixed with a metal, for example, with an alkali metal, an alkaline earth metal, or a rare earth metal, more specifically, 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.

[0172] Second electron transport layer:

[0173] The thickness of the second electron transport layer is generally 10 nm to 40 nm. 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.

[0174] When the organic electron transport material is mixed with a metal compound material, for example, with an alkali metal compound, an alkaline earth metal compound, or a rare earth metal compound, more specifically, with a lithium metal compound, a calcium metal compound, a magnesium metal compound, a samarium metal compound, or a ytterbium metal compound, and more specifically, with lithium 8-hydroxyquinoline, lithium fluoride, magnesium fluoride, ytterbium fluoride, or calcium fluoride. When mixed with the metal compound, the weight proportion of the organic electron transport material can be 20% to 80%, 20% to 40%, 40% to 60%, or 60% to 80%.

[0175] When the organic electron transport material is mixed with a metal, for example, with an alkali metal, an alkaline earth metal, or a rare earth metal, more specifically, 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.

[0176] Charge generation layer:

[0177] When using a single-layer light-emitting device, holes and electrons are injected from the anode and cathode, respectively, eliminating the need for a charge generation layer. When using a dual-layer or multi-layer light-emitting device, a charge generation layer is required between the light-emitting layers to achieve charge generation, injection, and transport. The charge generation layer is located between the two light-emitting layers and is typically composed of a P / N-type dual-layer material. The P-type material is selected from the hole-injection materials mentioned above, and the N-type material is a mixture of 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, with lithium, magnesium, calcium, ytterbium, and samarium being more specific examples. When the organic electron transport material is mixed with the metal, the weight proportion of the organic electron transport material can range from 80% to 99%, 80% to 89%, 89% to 99%, 80% to 85%, 85% to 90%, 90% to 95%, or 95% to 99%, etc.

[0178] cathode:

[0179] The cathode requires a material with good electrical conductivity and surface flatness. To improve electron injection, materials with a low work function are generally selected. The cathode material can be a single-layer cathode, or a double-layer or multi-layer cathode, typically made of a metal or metal alloy. For a single-layer cathode, silver, copper, aluminum, gold, or alloys of these metals with other metals, such as rare earth metals, alkali metals, and alkaline earth metals, can be used. Examples include magnesium-indium alloys, magnesium-aluminum alloys, aluminum-potassium alloys, aluminum-scandium-potassium alloys, magnesium-silver alloys, silver-ytterbium alloys, and silver-samarium alloys. If a double-layer cathode is used, the cathode layer closer to the light-emitting layer can be made of alkali metals, alkaline earth metals, or rare earth metals, such as lithium, calcium, magnesium, and ytterbium, to enhance electron injection. The cathode layer farther from the light-emitting layer, primarily to enhance conductivity, can typically be made of silver, copper, aluminum, or gold, or alloys of these metals with other metals, such as rare earth metals, alkali metals, and alkaline earth metals. Examples include magnesium-indium alloys, magnesium-aluminum alloys, aluminum-potassium alloys, aluminum-scandium-potassium alloys, magnesium-silver alloys, silver-ytterbium alloys, and silver-samarium alloys. The cathode can also be formed as a thin film by methods such as evaporation and sputtering.

[0180] When light comes out from the anode side, the cathode is required to be opaque, and a cathode thicker than 100nm can be evaporated. When light comes out from the cathode side, the cathode is required to be transparent, with a transmittance greater than 40% and a thickness of 10nm to 20nm.

[0181] Covering:

[0182] The refractive index n and absorption coefficient of the single-layer cover layer need to meet the following conditions:

[0183] The refractive index between the wavelengths of 450 and 650 nm is n(450-650 nm)>1.8, and the extinction coefficient between the wavelengths of 450 and 650 nm is below 0.1; the extinction coefficient at 380 nm is greater than 0.2; the difference between the refractive index of 450 nm and the refractive index of 530 nm is n(450 nm)-n(530 nm)<0.5, more preferably n(450 nm)-n(530 nm)<0.3; the difference between the refractive index of 510 nm and the refractive index of 620 nm is n(510 nm)-n(620 nm)<0.4, more preferably the difference between the refractive index of 510 nm and the refractive index of 620 nm is n(510 nm)-n(620 nm)<0.2.

[0184] Materials that can meet the requirements of the cover layer for the refractive index n can further achieve high luminous efficiency of the device, while at the same time achieving more balanced light extraction efficiency and viewing angles for red, green, and blue light.

[0185] 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.

[0186] The covering layer is formed after the translucent 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 translucent cathode between 450nm and 650nm is ≥65%, for example, 68%, 69%, 73%, 77%, 79%, 83%, 88%, 93%, etc.

[0187] When two covering layers are used, the refractive index n and absorption coefficient need to meet the following conditions:

[0188] 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.

[0189] The covering layer away from the cathode side (the second covering layer) has a refractive index n450~650nm>1.8 between wavelengths of 450~650nm, and an extinction coefficient between wavelengths of 450~650nm is below 0.1; the extinction coefficient at 380nm is greater than 0.1, and more preferably greater than 0.2.

[0190] The difference between the refractive index at 450 nm and the refractive index at 530 nm, n(450 nm)-n(530 nm), is less than 0.5, and more preferably, the difference between the refractive index at 450 nm and the refractive index at 530 nm, n(450 nm)-n(530 nm), is less than 0.3;

[0191] 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.

[0192] 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.

[0193] The thickness of the covering layer close to the cathode side (first covering layer) is 5nm to 40nm, for example: 5nm, 7nm, 10nm, 12nm, 15nm, 18nm, 20nm, 22nm, 25nm, 27nm, 30nm, 32nm, 34nm, 36nm, 38nm, 40nm, etc.

[0194] The thickness of the covering layer away from the cathode side (the second covering layer) 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.

[0195] On the other hand, the present application further provides a display device comprising the above-mentioned organic electroluminescent device.

[0196] Below in conjunction with the embodiment of the present application, the technical scheme of the present application is clearly and completely described. Unless otherwise specified, the reagents and raw materials used can be purchased through commercial channels. The experimental methods for which specific conditions are not specified in the following examples are usually measured in accordance with national standards. If there is no corresponding national standard, then according to general international standards, conventional methods and conditions, or according to the conditions recommended by the manufacturer, or according to the product specifications, select. Unless otherwise specified, all parts are parts by weight, and all percentages are percentages by weight.

[0197] Measurement instruments and methods

[0198]

Mass Spectrometry and Nuclear Magnetic Resonance

[0199] In this application, mass spectra were measured using a Waters Corporation single quadrupole mass spectrometer, and nuclear magnetic resonance was measured using a 400 MHz nuclear magnetic resonance instrument (manufactured by Bruker, Germany).

[0200]

Raw materials and reagents

[0201] 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. 1 H NMR data were measured using a 400 MHz nuclear magnetic resonance spectrometer (Bruker, Germany); HPLC data were measured using a Waters Corporation UPLC ultra-high performance liquid chromatograph. LC-MS (liquid chromatography-mass spectrometry) was performed on a Waters Corporation UPLC+SQD2 instrument.

[0202]

Cross-coupling

[0203] The synthesis of the triarylamine organic compound represented by formula (a) can be carried out using known methods. For example, a cross-coupling reaction using a transition metal such as nickel or palladium can be performed. Another synthesis method is a CC, CN coupling reaction using a transition metal such as magnesium or zinc. Due to the mild reaction conditions and excellent selectivity for various functional groups, the Suzuki and Buchwald reactions are preferred. 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.

[0204] 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 the reaction is stirred under reflux. After the desired reaction time, the reaction system is cooled, water is added, and the precipitated solid is washed and then vacuum-dried to obtain a crude product. The crude product is purified (including but not limited to silica gel column chromatography) to obtain the product.

[0205] The embodiments provided by the present invention can be synthesized by referring to the following general preparation routes:

[0206]

[0207] In particular, when L0 is selected from a single bond, the intermediate iii reacts directly with vii to obtain the corresponding target molecule.

[0208] The following describes the embodiments of the present invention through specific examples.

[0209] Example 1

[0210]

[0211] Synthesis of intermediate 1-iii

[0212] Under an argon atmosphere, compound 1-i (100 mmol, 1 eq), compound 1-ii (100 mmol), Pd(PPh3)4 (1 mmol, 1% eq), a 1.5 M aqueous solution of potassium carbonate (50 mL, 0.75 eq) and tetrahydrofuran (1000 mL) were added to the reaction vessel, stirring was started, the temperature was raised to reflux and the reaction was allowed to proceed overnight. Thin layer chromatography (TLC) analysis showed that there was essentially no starting material remaining. The reaction system was cooled to room temperature and 800 mL of water was added. A large amount of solid precipitated and was filtered. The filter cake was washed three times with water and dried under vacuum. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / hexane) to obtain compound 1-iii in a yield of 84.5%.

[0213] Synthesis of compound 1

[0214] Under an argon atmosphere, compound 1-iii (100 mmol, 1 eq), compound 1-vii (100 mmol, 1 eq), sodium tert-butoxide (240 mmol, 2.4 eq), bis(dibenzylideneacetonepalladium) (1 mmol, 1% eq), tri-tert-butylphosphine (5 mmol, 5% eq), and anhydrous toluene (1000 mL) were added to a reaction vessel. Stirring was initiated, the temperature was raised to 140°C, and the reaction was allowed to proceed for 15 hours. Thin-layer chromatography (TLC) analysis revealed virtually no residual starting material. The reaction mixture was cooled to room temperature, 1000 mL of water was added, and the mixture was filtered. The filter cake was washed with copious amounts of water and dried under vacuum. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate / hexane) to yield the target compound 1. The total yield for the two-step reaction was 62.5%.

[0215] Referring to the preparation method of compound 1, the compounds listed in Table 1 were synthesized. For each compound x, the raw materials or intermediates i, ii, v, and vii involved in the above preparation method are represented by xi, x-ii, xv, and x-vii, respectively. The main raw materials used, the synthesized intermediates, the yields, and the mass spectrometry data are shown in Table 1.

[0216] Table 1

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223] The NMR data of the representative compounds involved in the synthesis examples are shown in Table 2.

[0224] Table 2

[0225]

[0226]

[0227] Device Example:

[0228] The compounds used in the device are all purified by sublimation, and the purity is greater than 99.98%.

[0229] The compound involved in the present invention can be used as an electron blocking layer material for OLED devices. The specific device manufacturing method and test results are given below.

[0230] Green light device embodiment 1:

[0231] According to Figure 1 The structure shown is used to make a green bottom-emitting organic electroluminescent device. The preparation process is as follows: On a glass substrate 101, a transparent ITO film layer (thickness 150nm) is formed by magnetron sputtering 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 M2 (thickness 100nm) and compound 1 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 electron blocking layer 105, compound M3, compound M4 and compound M5 are co-evaporated at a mass ratio of 45:45:10 to form an organic light-emitting layer 106 (thickness 40nm). Subsequently, compound M6 was sequentially evaporated on the surface of the organic light-emitting layer to form a hole-blocking layer 107 (10 nm thick). Compound M7 and LiQ, mixed in a 4:6 mass ratio, were then formed into an electron-transporting layer 108 (30 nm thick). Finally, magnesium (Mg) and silver (Ag) were mixed and deposited on the surface of the electron-transporting layer 108 at a 1:9 vapor deposition rate to form a 10 nm thick second electrode 109, serving as the cathode. This completed the fabrication of the organic light-emitting device.

[0232] The chemical structures of compounds M1 to M7 and LiQ are shown in Table 3.

[0233] Table 3

[0234]

[0235] Green Light Device Examples 2 to 30

[0236] Green light device embodiments 2 to 30 were prepared using the same method as green light device embodiment 1, except that, when forming the electron blocking layer, the compounds in Table 4 were used instead of compound 1.

[0237] Green Light Device Comparative Examples 1 to 3

[0238] The organic electroluminescent device was prepared by the same method as in Example 1 of the green light device, except that compounds C1 to C3 (chemical structures shown below) were used instead of compound 1 when forming the electron blocking layer material.

[0239]

[0240] The operating voltage and efficiency of the organic electroluminescent device prepared above were calculated by a computer-controlled Keithley 2400 test system (test current was 20 mA / cm 2 The device lifetime under dark conditions was measured using a Flustar lifetime measurement system equipped with a power supply and a photodiode as a detection unit (test conditions: constant current 20 mA / cm 2 LT95 is the time it takes for the brightness to decrease from the initial brightness to 95%. The device capacitance was tested using a Tonghui TH2829A test system under a 1kHz AC signal source. The test results are shown in Table 4.

[0241] Table 4

[0242]

[0243]

[0244] Blu-ray device embodiment 1:

[0245] According to Figure 2 The structure shown is used to make a blue top-emitting organic electroluminescent device. The preparation process is as follows: On a glass substrate 101, a transparent ITO film layer (thickness 150nm) is formed by magnetron sputtering 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 M2 (thickness 100nm) and compound 3 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 electron blocking layer 105, compound M8 and compound M9 are co-evaporated at a mass ratio of 95:5 to form an organic light-emitting layer 106 (thickness 30nm). Subsequently, compound M6 was sequentially evaporated on the surface of the organic light-emitting layer to form a hole-blocking layer 107 (10 nm thick). Compound M7 and LiQ, mixed in a 4:6 mass ratio, were then formed into an electron-transporting layer 108 (30 nm thick). Subsequently, magnesium (Mg) and silver (Ag) were mixed and deposited on the surface of the electron-transporting layer 108 at a 1:9 evaporation rate to form a 10 nm thick second electrode 109, serving as the cathode. Finally, compound M10 was evaporated to a thickness of 70 nm as a capping layer, completing the fabrication of the organic light-emitting device.

[0246]

[0247] Blue light device embodiments 2 to 10

[0248] Green light device embodiments 2 to 10 were prepared using the same method as green light device embodiment 1, except that, when forming the electron blocking layer, compound 3 was replaced by the compounds in Table 5.

[0249] Comparative Examples 1 to 3 of Blue Light Devices

[0250] The organic electroluminescent device was prepared by the same method as in Example 1 of the blue light device, except that compounds C2 to C4 (the chemical structure of C4 is shown below) were used to replace compound 1 when forming the electron blocking layer.

[0251]

[0252] The operating voltage and efficiency of the organic electroluminescent device prepared above were calculated by a computer-controlled Keithley 2400 test system (test current was 20 mA / cm 2 The device lifetime under dark conditions was measured using a Flustar lifetime measurement system equipped with a power supply and a photodiode as a detection unit (test conditions: constant current 20 mA / cm 2 LT95 is the time it takes for the brightness to decrease from the initial brightness to 95%. The device capacitance was tested using a Tonghui TH2829A test system under a 1kHz AC signal source. The test results are shown in Table 5.

[0253] Table 5

[0254]

[0255]

[0256] Combined with Table 4, it can be seen that when the compounds of the present invention are used as electron blocking layer materials in green light device Examples 1-30, compared with Comparative Examples 1-3, the operating voltage of the device is reduced by at least 5.1%, the luminous efficiency is increased by at least 6.8%, the life is increased by at least 21.5%, and the capacitance is reduced by at least 27.6%.

[0257] Combined with Table 5, it can be seen that when the compounds of the present invention are used as electron blocking layer materials in blue light device Examples 1-10, compared with Comparative Examples 4-6, the operating voltage of the device is reduced by at least 5.0%, the luminous efficiency is increased by at least 4.1%, the life is increased by at least 10.7%, and the capacitance is reduced by at least 26.7%.

[0258] Therefore, the triarylamine organic compound of the present invention has great application value when used in organic photoelectric devices.

[0259] The above description is only a preferred specific embodiment of the present invention, but the scope of protection of the present invention is not limited thereto. Any technician familiar with the technical field, within the technical scope disclosed by the present invention, who makes equivalent replacements or changes based on the technical solution and inventive concept of the present invention, should be covered by the scope of protection of the present invention.

Claims

1. A triarylamine organic compound, characterized in that: The chemical structure of the triarylamine organic compound is shown in formula (a): in, One of A1 and A2 is selected from hydrogen, and the other is selected from the group described in formula (a-1): R3, R4 are each independently selected from hydrogen, deuterium, methyl or deuterated methyl; m is selected from 1 or 2; R1 and R2 are the same or different and are each independently selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, 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; or R1 and R2 are bonded to form a ring through a single bond; L0, L1, L2 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 3 to 30 carbon atoms; Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and satisfy the following conditions: at least one of Ar1 or Ar2 is selected from a group consisting of formula (a-2) or formula (a-3): in, R is selected from deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 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; n is selected from an integer between 0 and 7; X is selected from O or S; * indicates the bonding site.

2. The triarylamine organic compound according to claim 1, wherein Formula a-1 is selected from any one of the following groups:

3. The triarylamine organic compound according to claim 1, wherein R1 and R2 are the same as or different from each other and are each independently selected from a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms; or R1 and R2 are bonded to each other through a single bond to form a ring; wherein the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group.

4. The triarylamine organic compound according to claim 3, wherein R1 and R2 are each independently selected from a deuterated alkyl group having 1 to 4 carbon atoms, a deuterated cycloalkyl group having 3 to 10 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, or R1 and R2 are bonded to each other through a single bond to form a substituted or unsubstituted cycloalkyl or spirofluorenyl group; preferably, R1 and R2 are each independently selected from a methyl group, a perdeuterated methyl group, a phenyl group, a perdeuterated phenyl group; or R1 and R2 are bonded to each other through a single bond to form a cyclohexyl group, a cyclopentyl group or a spirofluorenyl group.

5. The triarylamine organic compound according to claim 1, wherein L0 is selected from a single bond, 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; wherein the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group.

6. The triarylamine organic compound according to claim 5, wherein L0 is selected from a single bond, or a substituted or unsubstituted group: phenylene, biphenylene, fluorenylene, dibenzofuranylene, dibenzothiophenylene; wherein the substituent in the "substituted or unsubstituted" group is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group.

7. The triarylamine organic compound according to claim 1, wherein Formula (a) is selected from any one of the following groups: Wherein, L1, L2, Ar1, Ar2, R3, R4, and m are the same as defined in claim 1.

8. The triarylamine organic compound according to claim 1 or 7, wherein L1 and L2 are each independently selected from a single bond, 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; wherein the substituent in the "substituted or unsubstituted" group is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group.

9. The triarylamine organic compound according to claim 8, wherein L1 and L2 are each independently selected from a single bond, or a substituted or unsubstituted group: phenylene, biphenylene, fluorenylene, dibenzofuranylene, dibenzothiophenylene; wherein the substituents in the "substituted or unsubstituted" group include deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group.

10. The triarylamine organic compound according to claim 1 or 7, wherein 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, and satisfy the following conditions: at least one of Ar1 or Ar2 is selected from a group consisting of formula (a-2) or formula (a-3); wherein the substituent in the "substituted or unsubstituted" group is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group.

11. The triarylamine organic compound according to claim 10, wherein Ar1 and Ar2 are each independently selected from the following substituted or unsubstituted groups: phenyl, diphenyl, terphenyl, fluorenyl, spirofluorenyl, spirofluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzofluorenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, wherein the substituent in the "substituted or unsubstituted" group is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group.

12. The triarylamine organic compound according to claim 1, wherein R is selected from deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, 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, wherein the substituent in the "substituted or unsubstituted" is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a deuterated methyl group, a phenyl group, a methylphenyl group, and a tert-butylphenyl group.

13. The triarylamine organic compound according to claim 12, wherein R is selected from deuterium, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a phenyl group, a biphenyl group, a methylphenyl group, and a tert-butylphenyl group.

14. The triarylamine organic compound according to any one of claims 1 to 12, wherein The triarylamine organic compound is selected from any one of the following chemical structures:

15. An organic layer comprising the triarylamine organic compound according to any one of claims 1 to 13.

16. Use of the triarylamine organic compound according to any one of claims 1 to 13 and / or the organic layer according to claim 14 in an organic optoelectronic device.

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

18. An organic photoelectric device, wherein the green light buffer layer comprises one or more triarylamine organic compounds according to claims 1-13.

19. A display or lighting device comprising the organic optoelectronic device according to claim 17.

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