An aromatic amine compound containing carbazole and an organic electroluminescent device

Abstract

The present invention relates to the technical field of organic optoelectronic materials, and particularly relates to an aromatic amine compound containing carbazole and an organic electroluminescent device. The aromatic amine compound containing carbazole provided by the present invention has good hole mobility, appropriate HOMO energy level and T1 value, good thermal stability and chemical stability. When applied to OLED devices, especially as a hole transport material, a host material for the light-emitting layer and a covering layer, it can effectively improve the light-emitting efficiency of the device, reduce the energy consumption of the device, lower the driving voltage, and also extend the service life of the device.

Description

Technical Field

[0001] The invention relates to the technical field of organic photoelectric materials, and in particular to an aromatic amine compound containing carbazole and an organic electroluminescent device thereof. Background Art

[0002] Organic Light-Emitting Diode (OLED) has the advantages of light weight, small size, wide viewing angle, fast response, wide operating temperature range, low energy consumption, high efficiency, good color purity, high clarity and good flexibility. It has a good application prospect in the field of lighting and display.

[0003] OLED devices are generally in the shape of a "sandwich". A light-emitting layer containing guest materials and host materials is set between the cathode and the anode. A certain working voltage is applied between the two electrodes. Under the action of the electric field, holes and electrons are injected from the anode and cathode respectively, reaching the light-emitting layer, recombining to produce excitons and releasing energy. The excitons then migrate and transfer the energy to the guest material. The electrons in the molecules of the guest material transition from the ground state to the excited state. Since the excited state is unstable, the electrons migrate back to the stable ground state, thereby releasing energy in the form of light and generating luminescence. In order to improve the driving voltage, luminous efficiency, color purity and other performances of OLED devices, more other organic functional layers are added between the anode and the light-emitting layer, and between the cathode and the light-emitting layer. In general, the organic functional layer between the anode and the light-emitting layer plays the role of injecting and transporting holes, which is called the hole transport region; the organic functional layer between the cathode and the light-emitting layer plays the role of injecting and transporting electrons, which is called the electron transport region. The hole transport region includes one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting auxiliary layer, etc., and the electron transport region includes one or more of an electron injection layer, an electron transport layer, a hole blocking layer, etc.

[0004] Among them, hole transport materials should generally have high hole mobility, appropriate highest occupied molecular orbital (HOMO) and triplet energy level (T1), good stability and film-forming properties. The host material generally needs to have a higher LUMO value and a lower HOMO value than the guest material. Aromatic amine compounds are currently one of the most widely used OLED materials. This type of compound has the properties that the above-mentioned hole transport materials should have, and aromatic amine compounds with different structures have different properties. They can be used as hole transport functional layers, light-emitting layer host materials or covering layers in OLED devices. Summary of the invention

[0005] To solve the above technical problems, the present invention provides an aromatic amine compound containing carbazole, which has good hole transport ability, appropriate HOMO energy level and T1 value, and high glass transition temperature (Tg), and can effectively improve the performance of OLED devices such as luminous efficiency, driving voltage and service life. It has the structure shown in formula (I-A) or formula (I-B):

[0006]

[0007] Wherein, the Ar 1 and Ar 2 are independently selected from one of substituted or unsubstituted C6-C20 aryl groups and substituted or unsubstituted C6-C20 heteroaryl groups;

[0008] The L 1 to L 3 are independently selected from one of a single bond, substituted or unsubstituted C6-C20 arylene groups and substituted or unsubstituted C6-C20 heteroarylene groups;

[0009] The L 4 is selected from one of substituted or unsubstituted C6-C20 arylene groups and substituted or unsubstituted C6-C20 heteroarylene groups;

[0010] In formula (I-A), A and B are independently selected from one of the structures shown in formula (i-a) to (i-c); in formula (I-B), A is selected from one of the structures shown in formula (i-a) to (i-c), and B is selected from one of formula (i-d) to (i-f):

[0011]

[0012] Wherein, the represents the connection with L' or L 3 and the "---" represents the fused bond with the five-membered N-containing heterocycle;

[0013] The a 1 is the same or different and is independently selected from 0, 1, 2 or 3 each time it appears; the b 1 is the same or different and is independently selected from 0, 1, 2, 3, 4 or 5 each time it appears; the c 1 is the same or different and is independently selected from 0, 1, 2, 3 or 4 each time it appears; the d 1 is the same or different and is independently selected from 0, 1, 2, 3, 4, 5 or 6 each time it appears;

[0014] The R 1Each occurrence is independently selected from H, D, a substituted or unsubstituted linear or branched C1-C4 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, or adjacent R 1 groups are linked to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbocyclic ring;

[0015] The R is selected from a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C6-C20 heteroaryl group;

[0016] The L’ is selected from a single bond, a substituted or unsubstituted C6-C20 arylene group;

[0017] The R’ is selected from H, D, a substituted or unsubstituted linear or branched C1-C4 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group;

[0018] The X is selected from O, S or CR 3 ’R 4 ’ and one of the R 3 ’ and R 4 ’ are independently selected from H, D, a substituted or unsubstituted linear or branched C1-C4 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group;

[0019] The a 1 ’ and b 1 ’ are independently selected from 0, 1, 2 or 3;

[0020] The R 1 ’ and R 2 ’ each occurrence is independently selected from H, D, a substituted or unsubstituted linear or branched C1-C4 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, or adjacent R 1 ’ groups are linked to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbocyclic ring, or adjacent R 2 ’ groups are linked to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbocyclic ring.

[0021] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer comprises one or more of the carbazole-containing aromatic amine compounds of the present invention.

[0022] Beneficial effects:

[0023] The carbazole-containing aromatic amine compound represented by formula (I-A) or formula (I-B) provided by the present invention has good hole mobility, appropriate HOMO energy level and T1 value, good thermal stability and chemical stability. When applied to OLED devices, especially as a hole transport material, a host material for the light-emitting layer and a covering layer, it can effectively improve the light-emitting efficiency of the device, reduce the energy consumption of the device, lower the driving voltage, and also extend the service life of the device. Detailed implementation manners

[0024] The technical solutions of the specific embodiments of the present invention will be described clearly and completely below. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative efforts fall within the protection scope of the present invention.

[0025] The halogen atom referred to in the present invention means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0026] The alkyl group referred to in the present invention means a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl groups include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but are not limited thereto; the branched-chain alkyl groups include isopropyl, isobutyl, sec-butyl, tert-butyl, isomeric groups of n-pentyl, isomeric groups of n-hexyl, isomeric groups of n-heptyl, isomeric groups of n-octyl, isomeric groups of n-nonyl, isomeric groups of n-decyl, etc., but are not limited thereto. The above alkyl groups are preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.

[0027] The cycloalkyl group referred to in the present invention means a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, etc., but are not limited thereto. The above cycloalkyl groups are preferably cyclopentyl, cyclohexyl, cyclopentenyl, 1-adamantyl, 2-adamantyl, norbornyl.

[0028] The cycloalkenyl group described in the present invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkene molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto. The above cycloalkyl group is preferably cyclopentenyl, cyclohexenyl.

[0029] The cycloalkynyl group described in the present invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkyne molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropynyl, cyclobutynyl, cyclopentynyl, cyclohexynyl, cycloheptynyl, etc., but are not limited thereto. The above cycloalkyl group is preferably cyclopentynyl, cyclohexynyl.

[0030] The heterocyclic group described in the present invention refers to a group formed by removing one hydrogen atom from a heterocyclic molecule in which the atoms constituting the ring contain at least one heteroatom in addition to carbon atoms. The heteroatoms include nitrogen atom, oxygen atom, sulfur atom, silicon atom, etc., and are preferably nitrogen atom, oxygen atom, sulfur atom. It preferably contains 1 to 3 heteroatoms, more preferably 1 to 2 heteroatoms, and particularly preferably 1 heteroatom. It preferably has 3 to 15 ring atoms, more preferably 3 to 12 ring atoms, and particularly preferably 5 to 6 ring atoms. Examples may include oxiranyl, thioethylenyl, aziridinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, etc., but are not limited thereto. The above heterocyclic group is preferably pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl.

[0031] The aryl group described in the present invention refers to the general term of a monovalent group remaining after removing one hydrogen atom from the aromatic nucleus carbon of an aromatic compound molecule. It can be a monocyclic aryl group, a polycyclic aryl group or a fused-ring aryl group, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl group refers to an aryl group having only one aromatic ring in the molecule, for example, phenyl, etc., but is not limited thereto; the polycyclic aryl group refers to an aryl group having two or more independent aromatic rings in the molecule, for example, biphenyl, terphenyl, etc., but is not limited thereto; the fused-ring aryl group refers to an aryl group having two or more aromatic rings and fused to each other by sharing two adjacent carbon atoms, for example, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylenyl, fluoranthenyl, spirobifluorenyl, etc., but is not limited thereto. The above aryl group is preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl.

[0032] The heteroaryl group described in the present invention refers to the general term for groups obtained by replacing one or more aryl nuclear carbon atoms in an aryl group with heteroatoms, where the heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. The bonding site of the heteroaryl group can be located on a ring-forming carbon atom or on a ring-forming nitrogen atom, and the heteroaryl group can be a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a fused-ring heteroaryl group. The monocyclic heteroaryl group includes, but is not limited to, pyridyl, pyrimidinyl, triazinyl, furyl, thienyl, pyrrolyl, imidazolyl, etc.; the polycyclic heteroaryl group includes, but is not limited to, bipyridyl, bipyrimidinyl, phenylpyridyl, etc.; the fused-ring heteroaryl group includes, but is not limited to, quinolinyl, isoquinolinyl, indolyl, benzothienyl, benzofuryl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuryl, benzodibenzofuryl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiinyl, etc. The above heteroaryl groups are preferably pyridyl, pyrimidinyl, thienyl, furyl, benzothienyl, benzofuryl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuryl, dibenzothienyl, benzodibenzothienyl, benzodibenzofuryl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenoxathiinyl.

[0033] In the present invention, the arylene group means an aryl group having two bonding sites, that is, a divalent group. Regarding this, the description of the aryl group provided above can be applied, with the difference being that the arylene group is a divalent group.

[0034] In the present invention, the heteroarylene group means a heteroaryl group having two bonding sites, that is, a divalent group. Regarding this, the description of the heteroaryl group provided above can be applied, with the difference being that the heteroarylene group is a divalent group.

[0035] "Substituted" as described in the present invention means that a hydrogen atom in certain functional groups is replaced by another atom or functional group (i.e., a substituent), and the position of substitution is not restricted as long as it is a position where a hydrogen atom is substituted, and when two or more are substituted, the two or more substituents can be the same or different from each other.

[0036] "Substituted or unsubstituted" as used in the present invention means not substituted or substituted with one or more substituents selected from the group consisting of: a deuterium atom, a halogen atom, an amino group, a cyano group, a nitro group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C3-C30 heterocyclic group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C2-C60 heteroaryl group, a silyl group, preferably a halogen atom, a cyano group, a nitro group, a C1-C12 alkyl group, a C3-C12 cycloalkyl group, a C3-C12 cycloalkenyl group, a C3-C12 heterocyclic group, a C6-C30 aryl group, a C3-C30 heteroaryl group, a silyl group; when substituted with a plurality of substituents, the plurality of substituents may be the same or different; preferably, it means not substituted or substituted with one or more substituents selected from the group consisting of: a deuterium atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a nitro group, a methyl group, a trifluoromethyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a cyclopropyl group, a deuterium-substituted cyclopropyl group, a methyl-substituted cyclopropyl group, an ethyl-substituted cyclopropyl group, a cyclobutyl group, a deuterium-substituted cyclobutyl group, a methyl-substituted cyclobutyl group, an ethyl-substituted cyclobutyl group, a cyclopentyl group, a deuterium-substituted cyclopentyl group, a methyl-substituted cyclopentyl group, an ethyl-substituted cyclopentyl group, a cyclohexyl group, a deuterium-substituted cyclohexyl group, a methyl-substituted cyclohexyl group, an ethyl-substituted cyclohexyl group, a n-propyl-substituted cyclohexyl group, a n-butyl-substituted cyclohexyl group, a cyclohexane-substituted cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a deuterium-substituted cyclopentenyl group, a methyl-substituted cyclopentenyl group, an ethyl-substituted cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, an adamantyl group, a deuterium-substituted adamantyl group, a methyl-substituted adamantyl group, an ethyl-substituted adamantyl group, a norbornyl group, a deuterium-substituted norbornyl group, a methyl-substituted norbornyl group, an ethyl-substituted norbornyl group, a pyrrolidinyl group, a piperidinyl group, a morpholinyl group, a thiomorpholinyl group, a methyl-substituted piperazinyl group, an ethyl-substituted piperazinyl group, a phenyl-substituted piperazinyl group, a naphthyl-substituted piperazinyl group, a methoxy group, an ethoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenylenyl group, a pyrenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a spirobifluorenyl group, a spiro-cyclopentyl-fluorenyl group, a spiro-cyclohexyl-fluorenyl group, a spiro-adamantyl-fluorenyl group, a spiro-cyclopentenyl-fluorenyl group, a spiro-cyclohexenyl-fluorenyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, an N-phenylcarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a trimethylsilyl group, a triphenylsilyl group; when substituted with a plurality of substituents, the plurality of substituents may be the same or different, and two adjacent substituents may be linked to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbocyclic ring.

[0037] In this specification, when the position of a substituent on an aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional sites of the aromatic ring. For example, can represent and so on.

[0038] In this specification, when the bond where a substituent or a connecting site is located passes through two or more rings, it indicates that it can be attached to any of the two or more rings, specifically, it can be attached to any of the corresponding optional sites of the rings. For example, can represent can represent and so on.

[0039] The ring structure formed by connection as described in the present invention means that each group is connected to each other through chemical bonds, and optionally forms a double bond / triple bond, and can form an aromatic group, as exemplified below:

[0040]

[0041]

[0042] For example, the connected and formed substituted or unsubstituted saturated or unsaturated C3-C6 carbocyclic ring can be substituted or unsubstituted: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cyclopropyne, cyclobutyne, cyclopentyne, cyclohexyne, benzene ring, etc., but not limited thereto.

[0043] The present invention provides an aromatic amine compound containing carbazole, having the structure shown in formula (I-A) or formula (I-B):

[0044]

[0045] Wherein, the Ar 1 , Ar 2 are independently selected from one of substituted or unsubstituted C6-C20 aryl groups, substituted or unsubstituted C6-C20 heteroaryl groups;

[0046] The L 1 -L 3 are independently selected from one of a single bond, substituted or unsubstituted C6-C20 arylene groups, substituted or unsubstituted C6-C20 heteroarylene groups;

[0047] The L 4 is selected from one of substituted or unsubstituted C6-C20 arylene groups, substituted or unsubstituted C6-C20 heteroarylene groups;

[0048] In formula (I-A), A and B are independently selected from one of the structures shown in formulas (i-a) to (i-c); in formula (I-B), A is selected from one of the structures shown in formulas (i-a) to (i-c), and B is selected from one of formulas (i-d) to (i-f):

[0049]

[0050] wherein, the represents the connection with L’ or L 3 and the "---" represents the fused bond with a five-membered N-containing heterocycle;

[0051] Each occurrence of a 1 is independently selected from 0, 1, 2 or 3; each occurrence of b 1 is independently selected from 0, 1, 2, 3, 4 or 5; each occurrence of c 1 is independently selected from 0, 1, 2, 3 or 4; each occurrence of d 1 is independently selected from 0, 1, 2, 3, 4, 5 or 6;

[0052] Each occurrence of R 1 is independently selected from H, D, a substituted or unsubstituted C1-C4 linear or branched alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C6-C20 aryl, a substituted or unsubstituted C3-C20 heteroaryl, or adjacent R 1 are connected to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbocycle;

[0053] R is selected from a substituted or unsubstituted C6-C20 aryl, a substituted or unsubstituted C6-C20 heteroaryl;

[0054] L’ is selected from a single bond, a substituted or unsubstituted C6-C20 arylene;

[0055] Each occurrence of R’ is independently selected from H, D, a substituted or unsubstituted C1-C4 linear or branched alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C6-C20 aryl, a substituted or unsubstituted C3-C20 heteroaryl;

[0056] X is selected from O, S or CR 3 ’R 4 ’, and R 3 ’ and R 4is independently selected from one of H, D, a substituted or unsubstituted C1-C4 straight-chain or branched alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, and a substituted or unsubstituted C6-C20 aryl group;

[0057] said a 1 ’, b 1 is independently selected from 0, 1, 2, or 3;

[0058] said R 1 ’, R 2 ’ is, each time it appears, the same as or different from one of H, D, a substituted or unsubstituted C1-C4 straight-chain or branched alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, and a substituted or unsubstituted C3-C20 heteroaryl group, or adjacent R 1 ’ are connected to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbocyclic ring, or adjacent R 2 ’ are connected to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbocyclic ring.

[0059] Preferably, the substituent in the "substituted or unsubstituted" is selected from a deuterium atom; a C1-C12 straight-chain or branched-chain alkyl group substituted or unsubstituted by one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a C3-C12 cycloalkyl group substituted or unsubstituted by one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a C3-C12 cycloalkenyl group substituted or unsubstituted by one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a C3-C12 heterocyclic group substituted or unsubstituted by one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a C6-C30 aryl group substituted or unsubstituted by one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a C3-C30 heteroaryl group substituted or unsubstituted by one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; and a silyl group substituted or unsubstituted by one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group. At least one of O, S, N, Si, and Se is contained in the heterocyclic group or heteroaryl group. The substituent is one or more. When there are multiple substituents, the multiple substituents are the same or different. When there are multiple substituents, two adjacent substituents may be connected to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbocyclic ring.

[0060] Preferably, the substituent in the "substituted or unsubstituted" is selected from a deuterium atom; a methyl group; a deuterated methyl group; an ethyl group; a deuterated ethyl group; a n-propyl group; an isopropyl group; a deuterated isopropyl group; a n-butyl group; a sec-butyl group; an isobutyl group; a tert-butyl group; a deuterated tert-butyl group; a cyclopropyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a cyclobutyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a cyclopentyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a cyclohexyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a cyclopropenyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a tritium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a cyclobutenyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a cyclopentenyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a cyclohexenyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a adamantyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a norbornyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a phenyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a naphthyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group;An anthryl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a phenanthryl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a triphenylenyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a 9,9-dimethylfluorenyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a 9,9-diphenylfluorenyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a spirobifluorenyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a spiro-cyclopentyl-fluorenyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a spiro-cyclohexyl-fluorenyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a spiro-adamantyl-fluorenyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a spiro-cyclopentenyl-fluorenyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a spiro-cyclohexenyl-fluorenyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a carbazolyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a dibenzofuranyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group;A dibenzothiophenyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a pyrrolidinyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a piperidinyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a morpholinyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a thiomorpholinyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a piperazinyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; and a silyl group substituted or unsubstituted with one or more members selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group, wherein the substituent(s) is / are one or more, and when there are multiple substituents, the multiple substituents are the same or different.;

[0061] Preferably, the Ar 1 and Ar 2 are independently selected from one of the structures shown below:

[0062]

[0063] wherein, a 2 is selected from 0, 1, 2, 3, 4 or 5, b 2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, c 2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, d 2 is selected from 0, 1, 2 or 3, e 2 is selected from 0, 1, 2, 3 or 4; f 2 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0064] The R 2Each occurrence is independently selected from H, D, a substituted or unsubstituted C1-C4 straight-chain or branched-chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C3-C10 heterocyclic group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, or two adjacent Rs 2 are linked together to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbocyclic ring;

[0065] The R 3 is selected from a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group;

[0066] The R 4 to R 6 are independently selected from H, D, a substituted or unsubstituted C1-C4 straight-chain or branched-chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, or R 4 is linked to R 5 to form a substituted or unsubstituted saturated or unsaturated C3-C10 carbocyclic ring.

[0067] Preferably, each occurrence of the R 2 is independently selected from H, D, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, tert-butyl, deuterated tert-butyl, or one of the following structures:

[0068]

[0069] wherein, each occurrence of the a 11 is independently selected from 0, 1, 2, 3, 4 or 5; each occurrence of the b 11 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; each occurrence of the c 11 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; each occurrence of the d 11 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; each occurrence of the e 11 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15; each occurrence of the f 11 is independently selected from 0, 1, 2 or 3; each occurrence of the g 11 is independently selected from 0, 1, 2, 3 or 4;

[0070] The R11 Each occurrence is independently selected from H, D, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, tert-butyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, adamantyl, deuterated adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, deuterated norbornyl, methyl-substituted norbornyl, phenyl, deuterated phenyl, methyl-substituted phenyl, deuterated methyl-substituted phenyl, isopropyl-substituted phenyl, deuterated isopropyl-substituted phenyl, tert-butyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, adamantyl-substituted phenyl, norbornyl-substituted phenyl, naphthyl, deuterated naphthyl, anthracenyl, deuterated anthracenyl, phenanthryl, deuterated phenanthryl, triphenylenyl, deuterated triphenylenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, 9-phenylcarbazolyl.

[0071] Preferably, said R 2 Each occurrence is independently selected from H, D, methyl, deuterated methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, or one of the following structures:

[0072]

[0073]

[0074] Preferably, said R 3 Is selected from one of the following structures:

[0075]

[0076] Wherein, said a 11 , b 11 , c 11 , d 11 , f 11 , g 11 , R 11 Are as described in the present invention;

[0077] Said R 12 , R 13 Are independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted phenyl, or R 12 And R 13 Are linked to form a saturated or unsaturated substituted or unsubstituted C3-C10 carbocycle.

[0078] Preferably, said R3 Selected from one of the structures shown below:

[0079]

[0080]

[0081]

[0082]

[0083] The said R 4 ~R 6 Are independently selected from methyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, tert-butyl, deuterated tert-butyl or one of the structures shown below:

[0084]

[0085] Wherein, the said a 11 , b 11 , R 11 Are all as described in the present invention.

[0086] The said R 4 ~R 6 Are independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl or one of the structures shown below:

[0087]

[0088] Preferably, the said Ar 1 , Ar 2 Are independently selected from one of the structures shown below:

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095] Preferably, the said L 1 ~L 3 Are independently selected from a single bond or one of the structures shown below, and the said L 4 Is selected from one of the structures shown below:

[0096]

[0097] wherein the said a 21 is, each time it appears, independently selected from 0, 1, 2, 3 or 4; the said b 21 is, each time it appears, independently selected from 0, 1, 2, 3, 4, 5 or 6; the said c 21 is, each time it appears, independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the said d 21 is, each time it appears, independently selected from 0, 1, 2 or 3;

[0098] The said R 21 has the same definition as the R described in the present invention; 2

[0099] The said R 22 , R 23 has the same definition as the R described in the present invention; 4 , R 5

[0100] The said R 24 has the same definition as the R described in the present invention; 3

[0101] Preferably, the said L 1 ~L 3 are independently selected from a single bond or one of the structures shown below, and the said L 4 is selected from one of the structures shown below:

[0102]

[0103]

[0104] Preferably, the said R has the same definition as the R described in the present invention; 3

[0105] Preferably, the said R 1 has the same definition as the R described in the present invention; 2

[0106] Preferably, the said is selected from one of the structures shown below:

[0107]

[0108] wherein the said R, R 1 , a 1 , b 1 are all as described in the present invention.

[0109] ​​​​​Preferably, the is selected from one of the following structures:

[0110]

[0111] wherein the R, R 1 , a 1 , b 1 , c 1 , d 1 are all as described in the present invention.

[0112] Preferably, the R 1 ’, R 2 ’ has the same definition as the R 2 described in the present invention.

[0113] Preferably, the R’ has the same definition as the R 6 described in the present invention.

[0114] Preferably, the L’ has the same definition as the L 3 described in the present invention.

[0115] Preferably, the R 3 ’, R 4 ’ has the same definition as the R 4 , R 5 described in the present invention.

[0116] Preferably, the is selected from one of the following structures:

[0117]

[0118] wherein the a 1 ’, b 1 ’ are all as described in the present invention;

[0119] each occurrence of the R 11 ’, R 12 ’ is independently selected from H, D, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, tert-butyl, deuterated tert-butyl or one of the following structures:

[0120]

[0121] wherein the a 11 , b 11 , c 11 , d 11 , e 11 , f 11 , g 11 , R 11 are all as described in the present invention,

[0122] The said R 13 ’, R 14 ’ are independently selected from H, D, methyl, deuterated methyl, ethyl or one of the structures shown below:

[0123]

[0124] Wherein, the said a 11 , b 11 , R 11 are all as described in the present invention; preferably, each occurrence of the said R 11 is the same as or different from each other and is selected from H, D, methyl, deuterated methyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, or the R 13 ’ and R 14 ’ are connected to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbocyclic ring;

[0125] The said R 15 ’ is selected from methyl or one of the structures shown below:

[0126]

[0127] Wherein, the said a 11 , b 11 , R 11 are all as described in the present invention; preferably, each occurrence of the said R 11 is the same as or different from each other and is selected from H, D, methyl, deuterated methyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl;

[0128] The said L 11 ’ is selected from a single bond or one of the structures shown below:

[0129]

[0130] Wherein, the said a 21 , b 21 , c 21 , R 21 are all as described in the present invention.

[0131] Preferably, each occurrence of the said R 11 ’, R 12 ’ is the same as or different from each other and is selected from H, D, methyl, deuterated methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl or one of the structures shown below:

[0132]

[0133]

[0134] Preferably, the R 13 ’, R 14 ’ are independently selected from methyl, ethyl or one of the structures shown below:

[0135]

[0136] Preferably, the R 15 ’ is selected from methyl or one of the structures shown below:

[0137]

[0138] Preferably, the L 11 ’ is selected from a single bond or one of the structures shown below:

[0139]

[0140]

[0141] Preferably, the carbazole-containing aromatic amine compound has any one of the following general formulas (II-A) to (II-F):

[0142]

[0143] Among them, the Ar 1 , Ar 2 , L 1 to L 4 , R, a 1 , R 1 , a 1 ’, b 1 ’, R 11 ’, R 12 ’, R 13 ’, R 14 ’, R 15 ’, L 11 ’ are as described in the present invention.

[0144] Preferably, the carbazole-containing aromatic amine compound has any one of the following general formulas (III-A) to (III-F):

[0145]

[0146] Among them, the Ar 1 , Ar 2 , L 1 to L 4 , R, a 1 , R 1 , a 1 ’, b1 ’, R 11 ’, R 12 ’, R 13 ’, R 14 ’, R 15 ’ are all as described in the present invention.

[0147] Most preferably, the carbazole-containing aromatic amine compound is selected from one of the following compounds:

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159] The carbazole-containing aromatic amine compound described in the present invention can be prepared through the following synthetic route:

[0160] Among them, the structure shown in formula (I-A) can be prepared through the following two synthetic routes:

[0161] Route 1:

[0162]

[0163] Route 2:

[0164]

[0165] In Route 1 and Route 2, compound (a) undergoes a coupling reaction with compound (b) to form intermediate (c); intermediate (c) then undergoes a Suzuki coupling reaction with compound (d) or (d') to form intermediate (e) or (e'); intermediate (e) or (e') undergoes a ring closure reaction to obtain intermediate (f) or (f'); intermediate (f) or (f') undergoes an Ullmann reaction with compound (g) to obtain intermediate (h) or (h').

[0166] Then, in Route 1, intermediate (h) undergoes a Buchwald - hartwing coupling reaction with compound (i) to obtain the final product (I - A); in Route 2, intermediate (h') undergoes a Suzuki coupling reaction with compound (j) to form intermediate (k), intermediate (k) then undergoes a Buchwald - hartwing coupling reaction with compound (l) to form intermediate (m), and finally intermediate (m) undergoes a Buchwald - hartwing coupling reaction with compound (n) to obtain the final product (I - A).

[0167] The structure shown in formula (I - B) can be prepared through the following two synthetic routes:

[0168] Route 3:

[0169]

[0170] In Route 3, compound (a) undergoes a coupling reaction with compound (b) to obtain intermediate (c); intermediate (c) undergoes a Suzuki coupling reaction with compound (o) to obtain intermediate (p); intermediate (p) undergoes a ring closure reaction to obtain intermediate (q); intermediate (q) undergoes an Ullmann reaction with compound (r) to obtain intermediate (s); finally, intermediate (s) undergoes a Buchwald - hartwing coupling reaction with compound (i) to obtain the final product (I - B).

[0171] In the above routes, the A, B, L 1 ~L 4 、Ar 1 、Ar 2 、R、R’, R 1 ’、R 2 ’、X、a 1 ’、b 1 ’、L’ are all as described in the present invention, the X 1 ~X 7 independently selected from a chlorine atom, a bromine atom or an iodine atom, the Y 1 、Y 2 independently selected from B(OH) 2 or

[0172] The above synthetic route adopts reaction types commonly used in organic synthesis, and there are no special restrictions on the reaction conditions (for example, the selection, dosage, and addition sequence and method of reaction solvents, catalysts, ligands, bases, etc.). The raw materials for the above preparation method are easily available, the preparation process is simple, and the yield is excellent. The compounds represented by formula (I-A) or formula (I-B) provided by the present invention can also be synthesized by other conventional reaction types in organic synthesis, without special restrictions. The above is only an example of the synthetic route.

[0173] The present invention also provides an organic electroluminescent device, including an anode, a cathode, and an organic layer located between the anode and the cathode. The organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, and the organic layer contains one or more of the carbazole-containing aromatic amine compounds of the present invention.

[0174] Preferably, the hole transport region contains one or more of the carbazole-containing aromatic amine compounds of the present invention.

[0175] Preferably, the hole transport region includes one or more of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer.

[0176] Preferably, the hole transport region includes a hole injection layer and a hole transport layer, and one of the hole injection layer and the hole transport layer contains one or more of the carbazole-containing aromatic amine compounds of the present invention; more preferably, the hole transport layer contains one or more of the carbazole-containing aromatic amine compounds of the present invention.

[0177] Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, and one of the hole injection layer, the hole transport layer, and the light-emitting auxiliary layer contains one or more of the carbazole-containing aromatic amine compounds of the present invention.

[0178] Preferably, the light-emitting layer contains one or more of the carbazole-containing aromatic amine compounds of the present invention.

[0179] Preferably, the light-emitting layer includes a host material and a guest material, and the host material contains one or more of the carbazole-containing aromatic amine compounds of the present invention; more preferably, the host material contains one or more of the carbazole-containing aromatic amine compounds of the present invention and at least one other type of compound; even more preferably, the host material contains one or more of the carbazole-containing aromatic amine compounds of the present invention and at least one compound containing a triazine group.

[0180] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, an organic layer between the anode and the cathode, and a cover layer on a side of the cathode facing away from the anode. The organic layer includes a hole transport region, a light-emitting layer, and an electron transport region. The organic layer contains one or more of the carbazole-containing aromatic amine compounds of the present invention.

[0181] Preferably, the hole transport region contains one or more of the carbazole-containing aromatic amine compounds of the present invention.

[0182] Preferably, the hole transport region includes one or more of a hole injection layer, a hole transport layer, and a light-emission assisting layer.

[0183] Preferably, the hole transport region includes a hole injection layer and a hole transport layer, and one of the hole injection layer and the hole transport layer contains one or more of the carbazole-containing aromatic amine compounds of the present invention; more preferably, the hole transport layer contains one or more of the carbazole-containing aromatic amine compounds of the present invention.

[0184] Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emission assisting layer, and one of the hole injection layer, the hole transport layer, and the light-emission assisting layer contains one or more of the carbazole-containing aromatic amine compounds of the present invention.

[0185] Preferably, the light-emitting layer contains one or more of the carbazole-containing aromatic amine compounds of the present invention.

[0186] Preferably, the light-emitting layer includes a host material and a guest material, and the host material contains one or more of the carbazole-containing aromatic amine compounds of the present invention; more preferably, the host material contains one or more of the carbazole-containing aromatic amine compounds of the present invention and at least one other type of compound; even more preferably, the host material contains one or more of the carbazole-containing aromatic amine compounds of the present invention and at least one compound containing a triazine group.

[0187] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, an organic layer between the anode and the cathode, and a cover layer on a side of the cathode facing away from the anode. The organic layer includes a hole transport region, a light-emitting layer, and an electron transport region. The cover layer contains one or more of the carbazole-containing aromatic amine compounds of the present invention.

[0188] The hole injection layer described in the present invention may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. Triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, axleene compounds, and other substances with high hole injection properties can be used. Examples include 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HATCN), copper phthalocyanine (CuPC), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyano-p-benzoquinodimethane (F4-TCNQ), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT / PSS), and the carbazole-containing aromatic amine compound described in the present invention, but are not limited thereto.

[0189] The hole transport layer described in the present invention may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. Triarylamine compounds can be used, or other substances with a hole mobility of 10 -6 cm 2 / Vs or more can be used. Examples include N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'4”-tris(N,N-diphenylamino)triphenylamine (TDATA), and the carbazole-containing aromatic amine compound described in the present invention, but are not limited thereto.

[0190] The light-emission assisting layer described in the present invention may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. Triarylamine compounds, spirofluorene derivatives, dibenzofuran derivatives can be used, or other substances with appropriate HOMO and T1 energy levels can be used. Examples include TPD, NPB, N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenyl-N4'-[1,1':4',1”-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobifluorene-2-amine, N,N-bis([1,1'-biphenyl]-4-yl)-3'-(dibenz[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, and the carbazole-containing aromatic amine compound described in the present invention, but are not limited thereto.

[0191] The light-emitting layer described in the present invention may contain only the guest material, or may adopt the form of the guest material dispersed in the host material, and two host materials may be used to form a double-host material. The guest material may use fluorescent compounds, such as pyrene derivatives, fluoranthene derivatives, aromatic amine derivatives, etc. Examples may include 10-(2-benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizin-11-one (C545T), 4,4'-bis(9-ethyl-3-carbazolylvinyl)-1,1'-biphenyl (BCzVBi), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), etc. Phosphorescent materials may also be used, such as metal complexes such as iridium complexes, osmium complexes, platinum complexes, etc. Examples may include bis(4,6-difluorophenylpyridine-N,C2)picolyliridium(III) (FIrpic), tris(2-phenylpyridine)iridium(III) (Ir(ppy) 3 ), bis(2-phenylpyridine)(acetylacetonato)iridium(III) (Ir(ppy) 2 (acac)), etc. The host material is preferably a substance with a higher LUMO than the guest material and a lower HOMO than the guest material, such as metal complexes such as aluminum complexes or zinc complexes, heterocyclic compounds such as oxadiazole derivatives or benzimidazole derivatives, triazine derivatives, fused aromatic compounds such as carbazole derivatives or anthracene derivatives, aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives. Examples may include tris(8-hydroxyquinolinato)aluminum(III) (Alq 3 ), bis(2-methyl-8-hydroxyquinolinato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum(III) (BAlq), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBI), TPD, 4,4'-bis(9-carbazolyl)biphenyl (CBP), 4,4',4”-tris(carbazol-9-yl)triphenylamine (TCTA), 9,10-di(2-naphthyl)anthracene (ADN), the aromatic amine compound containing carbazole described in the present invention, but not limited thereto.

[0192] The electron transport region described in the present invention includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0193] The electron injection layer described in the present invention may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances, and one or more of the following substances may be selected: alkali metals, alkaline earth metals, halides of alkali metals, halides of alkaline earth metals, oxides of alkali metals, oxides of alkaline earth metals, alkali metal salts, alkaline earth metal salts, other substances with high electron injection properties. Examples may include Li, Ca, Sr, LiF, CsF, CaF 2, BaO, Li 2 CO 3 , CaCO 3 , Li 2 C 2 O 4 , Cs 2 C 2 O 4 , CsAlF 4 , LiOx, Yb, Tb, etc., but not limited thereto.

[0194] The electron transport layer described in the present invention can be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. Aluminum complexes, lithium complexes, beryllium complexes, zinc complexes, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, high-molecular compounds, etc. with high electron transport properties can be used. Examples include Alq 3 , lithium 8-hydroxyquinoline (Liq), beryllium bis(10-hydroxybenzo[h]quinoline) (BeBq 2 ), 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), BAlq, 2-(4-biphenylyl)-5-phenyloxadiazole (PBD), etc., but not limited thereto.

[0195] The hole blocking layer described in the present invention can be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. The selected material is required to have a T1 energy level higher than that of the light-emitting layer so as to block the energy loss of the light-emitting layer. In addition, the HOMO energy level of the selected material should be lower than the HOMO energy level of the host material of the light-emitting layer to play a role in blocking holes. Further, the electron mobility of the hole blocking layer material used is above 10 -6 cm 2 / Vs, which is beneficial to the transport of electrons. One or more of the following substances can be selected: aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, high-molecular compounds, etc. Examples include 1,3,5-tris(1-phenyl-1H-benzoimidazol-2-yl)benzene (TPBI), BAlq, etc.

[0196] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer;

[0197] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer;

[0198] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and an electron injection layer;

[0199] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0200] The anode of the present invention can be a reflective anode, such as a reflective film formed of silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb), or an alloy thereof, or can be a layer structure with a high work function and being transparent or semi-transparent, such as indium tin oxide (ITO), indium zinc oxide (ZnO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In 2 O 3 ) or tin oxide (SnO 2 ), which is specifically determined according to the type of device to be prepared. For example, if the device to be prepared is a bottom-emitting device (light emitting from the anode side), a transparent or semi-transparent anode needs to be made. If the device to be prepared is a top-emitting device (light emitting from the cathode side), a reflective anode needs to be made.

[0201] The cathode of the present invention can be a thin film made of lithium, calcium, lithium fluoride / calcium, lithium fluoride / aluminum, aluminum, silver, magnesium, magnesium-silver alloy, etc., and a reflective electrode, a transparent electrode, or a semi-transparent electrode can be made by adjusting the thickness of the film. If a bottom-emitting device needs to be prepared, a reflective cathode needs to be made. If a top-emitting device needs to be prepared, a transparent or semi-transparent cathode needs to be made.

[0202] The cover layer of the present invention includes a first cover layer and / or a second cover layer. When including the first cover layer or the second cover layer, it can be a single-layer structure composed of a single substance or a single-layer structure composed of different substances; when including the first cover layer and the second cover layer, it is a multi-layer structure composed of a single substance or different substances. The cover layer material can use organic or inorganic substances. For example, it can be metal halides, oxides, nitrides, oxynitrides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, arylamine compounds, etc. Examples can include LiF, CsF, MgF 2 , CaF 2 , CsCl, CuI, V 2 O 5 , WO 3 , MoO 3 , TiO 2 , ZrO, ZnO, SiO 2 , SiN, ZnS, Alq 3, Compound CP-1, Compound CP-2, Compound CP-3, Compound CP-4, and the carbazole-containing aromatic amine compounds described in the present invention, but not limited thereto.

[0203]

[0204] Each of the above organic layers, cathode, anode, and cover layer can be prepared by any one of vacuum evaporation, inkjet printing, sputtering, plasma, ion plating, spin coating, dipping, screen printing, etc. There is no special limitation on the film thickness of each layer, as long as good device performance can be obtained. Each of the above organic layers is preferably prepared by vacuum evaporation, inkjet printing, or spin coating.

[0205] The thickness of each of the above organic layers and cover layer is usually 5 nm to 100 μm, preferably 10 nm to 200 nm. The thickness of the anode and cathode is adjusted according to the required transparency.

[0206] The organic electroluminescent device provided by the present invention can be applied to fields such as lighting and display, and specifically can be exemplified as smartphone displays, tablet computer displays, smart wearable device displays, large-size displays such as TVs, VR, and automobile tail lights, etc.

[0207] The technical solutions and technical effects of the present invention will be further described below with reference to examples and comparative examples.

[0208] The mass spectrometry of the compounds of the present invention uses a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters Corporation in the UK, with chloroform as the solvent;

[0209] Elemental analysis uses a Vario EL cube type organic elemental analyzer from Elementar Company in Germany, and the sample mass is 5 - 10 mg.

[0210] Synthesis Example 1: Synthesis of Intermediates i-24, i-26, i-51, and i-90

[0211]

[0212] Under argon protection, add t-24 (0.98 g, 10.00 mmol), u-24 (3.97 g, 10.00 mmol), K 2 CO 3 (2.76 g, 20.00 mmol), Pd(OAc) 2 (0.02 g, 0.10 mmol), P(t-Bu) 3(0.43 mL of 0.5 M toluene solution, 0.20 mmol) and 50 mL of toluene were added. The mixture was stirred, and the above system was heated under reflux for 2 h. After the reaction was completed, the reaction mixture was cooled to room temperature, toluene was removed, and the mixture was extracted with dichloromethane and distilled water. The layers were separated by standing, and the organic phase was collected, dried over anhydrous magnesium sulfate, filtered, concentrated by distillation under reduced pressure, filtered by suction, and finally recrystallized from methanol to obtain intermediate i-24 (3.48 g, yield 84%), HPLC purity ≥ 99.75%. Mass spectrometry m / z: 414.2156 (theoretical value: 414.2144).

[0213] According to the preparation method of intermediate i-24, raw materials t and u were replaced in equimolar amounts to synthesize the following intermediate i:

[0214]

[0215] Synthesis Example 2: Synthesis of intermediates c-24, c-26, c-42, c-51, c-90, c-114, c-252, c-262, c-302, c-332

[0216]

[0217] Under argon protection, 315 mL of anhydrous tetrahydrofuran solution containing a-24 (56.76 g, 193.00 mmol) was added to a reaction flask, and the mixture was stirred at -78 °C. Then, 122 mL of 1.58 M n-butyllithium hexane solution was added dropwise. After stirring for 3 h, 383 mL of anhydrous tetrahydrofuran solution containing b-24 (31.85 g, 160.00 mmol) was added dropwise to the reaction flask, and the mixture was stirred for another 2 h and then at room temperature for 3 h. After the reaction was completed, 1 N hydrochloric acid aqueous solution was added to the reaction solution and stirred for 1 h, then distilled water was added to the reaction solution. The organic phase was collected and concentrated by distillation under reduced pressure. Glacial acetic acid (225 mL) and hydrochloric acid (11 mL) were added to the obtained mixture, and the mixture was heated and stirred at 120 °C for 2 h. After the reaction was completed, the reaction solution was placed in an ice-water bath to precipitate a solid product, which was filtered, washed with methanol, and dried to obtain intermediate c-24 (43.02 g, yield 77%). HPLC purity ≥ 99.68%, mass spectrometry m / z: 348.0165 (theoretical value 348.0150).

[0218] According to the preparation method of intermediate c-24, raw materials a and b were replaced in equimolar amounts to synthesize the following intermediate c:

[0219]

[0220] Synthesis Example 3: Synthesis of Compound 24

[0221]

[0222] Synthetic intermediate e-24

[0223] Under argon protection, add c-24 (32.13 g, 92.00 mmol), d-24 (18.53 g, 92.00 mmol), K 2 CO 3 (25.43 g, 184.00 mmol), Pd(PPh 3 ) 4 (1.06 g, 0.92 mmol) and 460 mL of a mixed solvent of toluene / ethanol / water (2:1:1) to the reaction flask, and heat the above system to reflux for 3 h. After the reaction is completed, wait for the reaction mixture to cool to room temperature, filter to obtain a filter cake, wash the filter cake with ethanol, and finally recrystallize the filter cake with toluene / ethanol = 10:1 to obtain intermediate e-24 (32.52 g, yield 83%), HPLC purity ≥99.67%. Mass spectrum m / z: 425.0833 (theoretical value: 425.0819).

[0224] Synthetic intermediate f-24

[0225] Under argon protection, add e-24 (27.68 g, 65.00 mmol), PPh 3 (42.59 g, 162.00 mmol) and (130 mL) o-DCB solution to the reaction flask, and heat to reflux with vigorous stirring for 21 h. After the reaction is completed, wait for the reaction mixture to cool to room temperature and concentrate under high vacuum. Purify the crude product by column chromatography on silica gel with hexane / ethyl acetate (9:1) to obtain intermediate f-24 (13.57 g, yield 53%), HPLC purity ≥99.72%. Mass spectrum m / z: 393.0937 (theoretical value: 393.0920). 1 1H NMR (500 MHz, CDCl3) (δ, ppm): 9.71 (s, 1H), 7.93 (s, 1H), 7.84 (s, 1H), 7.55 (d, 1H), 7.54 (d, 1H), 7.41 (d, 1H), 7.39 (d, 1H), 7.34 (dd, 2H), 7.23 (dd, 1H), 7.08 (dd, 1H), 6.98 (d, 1H), 6.97 (d, 1H), 1.54 (s, 3H).

[0226] Synthetic intermediate h-24

[0227] Under argon protection, add f-24 (12.60 g, 32.00 mmol), g-24 (5.02 g, 32.00 mmol), Pd(OAc)2 (0.14g, 0.63mmol), tri-tert-butylphosphine tetrafluoroborate (0.55g, 1.89mmol), sodium tert-butoxide (7.69g, 80mmol) and 270ml of toluene, the above system was heated to reflux for 5h. After the reaction was completed, the reaction mixture was cooled to room temperature, toluene was removed and extracted with dichloromethane and distilled water, and then the solvent was removed in vacuo, and recrystallized with dichloromethane / hexane to obtain intermediate h-24 (7.67g, yield 51%). HPLC purity ≥99.81%. Mass spectrum m / z: 469.1245 (theoretical value: 469.1233).

[0228] Synthesis of compound 24

[0229] Under argon protection, h-24 (2.35 g, 5.00 mmol), i-24 (2.07 g, 5.00 mmol), Pd 2 (dba) 3 (0.06g, 0.07mmol), BINAP (0.09g, 0.14mmol), sodium tert-butoxide (0.96g, 10mmol) and 25ml of toluene were heated under reflux for 7h under stirring. After the reaction was completed, it was cooled to room temperature, dichloromethane and distilled water were added to the mixture for extraction, and the mixture was allowed to stand for separation. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The temperature was lowered for crystallization, suction filtered, and finally recrystallized from toluene to obtain compound 24 (2.97g, 70%), HPLC purity ≧99.96%. Mass spectrum m / z: 847.3625 (theoretical value: 847.3611). Theoretical element content (%) C 63 H 37 D 5 N 2 O: C, 89.23; H, 5.59; N, 3.30. Measured element content (%): C, 89.19; H, 5.61; N, 3.27.

[0230] Synthesis Example 4: Synthesis of Compound 26

[0231]

[0232] According to the preparation method of Synthesis Example 3, c-24 was replaced by an equal molar amount of c-26, d-24 was replaced by an equal molar amount of d-26, and i-24 was replaced by an equal molar amount of i-26 to obtain compound 26 (3.08 g) with HPLC purity ≥ 99.93%. Mass spectrum m / z: 918.3626 (theoretical value: 918.3610). Theoretical element content (%) C 69 H 46 N 2O: C, 90.17; H, 5.04; N, 3.05. Measured elemental content (%): C, 90.21; H, 4.99; N, 3.10.

[0233] Synthesis Example 5: Synthesis of Compound 42

[0234]

[0235] According to the preparation method of Synthesis Example 3, replace c-24 with an equimolar amount of c-42 and i-24 with an equimolar amount of i-42 to obtain Compound 42 (3.04 g), HPLC purity ≥ 99.96%. Mass spectrometry m / z: 892.3465 (theoretical value: 892.3454). Theoretical elemental content (%) C 67 H 44 N 2 O: C, 90.11; H, 4.97; N, 3.14. Measured elemental content (%): C, 90.08; H, 5.01; N, 3.09.

[0236] Synthesis Example 6: Synthesis of Compound 51

[0237]

[0238] According to the preparation method of Synthesis Example 3, replace c-24 with an equimolar amount of c-51 and i-24 with an equimolar amount of i-51 to obtain Compound 51 (2.99 g), HPLC purity ≥ 99.95%. Mass spectrometry m / z: 879.3651 (theoretical value: 879.3665). Theoretical elemental content (%) C 64 H 37 D 7 N 2 S: C, 87.34; H, 5.84; N, 3.18. Measured elemental content (%): C, 87.28; H, 5.87; N, 3.23.

[0239] Synthesis Example 7: Synthesis of Compound 90

[0240]

[0241] According to the preparation method of Synthesis Example 3, replace c-24 with an equimolar amount of c-90, d-24 with an equimolar amount of d-26, and i-24 with an equimolar amount of i-90 to obtain Compound 90 (3.05 g), HPLC purity ≥ 99.95%. Mass spectrometry m / z: 871.3937 (theoretical value: 871.3947). Theoretical elemental content (%) C 63 H 37 D 9 N 2S: C, 86.76; H, 6.35; N, 3.21. Measured elemental content (%): C, 86.78; H, 6.40; N, 3.18.

[0242] Synthesis Example 8: Synthesis of Compound 100

[0243]

[0244] Synthesize Intermediate k-100

[0245] Under argon protection, add h-42 (7.98 g, 15.00 mmol), j-100 (2.05 g, 15.00 mmol), K 2 CO 3 (4.15 g, 30.00 mmol), Pd(PPh 3 ) 4 (0.17 g, 0.15 mmol) and 75 mL of a mixed solvent of toluene / ethanol / water (2:1:1) to the reaction flask, and heat the above system to reflux for 4 h. After the reaction is completed, wait for the reaction mixture to cool to room temperature, filter by suction to obtain a filter cake, wash the filter cake with ethanol, and finally recrystallize the filter cake with toluene / ethanol = 10:1 to obtain Intermediate k-100 (6.89 g, yield 78%), HPLC purity ≥ 99.82%. Mass spectrometry m / z: 588.2220 (theoretical value: 588.2202).

[0246] Synthesize Intermediate m-100

[0247] Under argon protection, add k-100 (5.89 g, 10.00 mmol), l-100 (2.33 g, 10.00 mmol), K 2 CO 3 (2.76 g, 20.00 mmol), Pd(OAc) 2 (0.02 g, 0.11 mmol), P(t-Bu) 3 (0.44 mL of a 0.5 M toluene solution, 0.22 mmol) and 50 ml of toluene to the reaction flask, stir the mixture, and heat the above system to reflux for 5 h. After the reaction is completed, cool to room temperature, add dichloromethane and distilled water to the mixture for extraction, let it stand for liquid separation, collect the organic phase, dry it with anhydrous magnesium sulfate, filter, concentrate the filtrate by vacuum distillation, filter by suction, and recrystallize with ethyl acetate to obtain Intermediate m-100 (5.26 g, yield 71%), HPLC purity ≥ 99.86%. Mass spectrometry m / z: 740.2811 (theoretical value: 740.2828).

[0248] Synthesize Compound 100

[0249] Under argon protection, m-100 (3.70 g, 5.00 mmol), l-100 (1.17 g, 5.00 mmol), Pd 2 (dba) 3 (0.06 g, 0.07 mmol), BINAP (0.09 g, 0.14 mmol), sodium tert-butoxide (0.96 g, 10 mmol) and 25 ml of toluene were added to the reaction flask, and the mixture was heated under reflux with stirring for 7 h. After the reaction was completed, it was cooled to room temperature, dichloromethane and distilled water were added to the mixture for extraction, and the layers were separated by standing. The organic phase was dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated by distillation under reduced pressure, crystallized by cooling, filtered by suction, and finally recrystallized from toluene to obtain compound 100 (2.99 g, 67%), HPLC purity ≥ 99.93%. Mass spectrometry m / z: 892.3441 (theoretical value: 892.3454). Theoretical elemental content (%) C 67 H 44 N 2 O: C, 90.11; H, 4.97; N, 3.14. Measured elemental content (%) C, 90.09; H, 5.01; N, 3.17.

[0250] Synthesis Example 9: Synthesis of Compound 114

[0251]

[0252] Synthesis of Intermediate h-114

[0253] According to the preparation method of intermediate h-24 in Synthesis Example 3, c-24 was replaced with an equimolar amount of c-116 to obtain intermediate h-114 (12.25 g), HPLC purity ≥ 99.83%. Mass spectrometry m / z: 531.1405 (theoretical value: 531.1390).

[0254] Synthesis of Compound 114

[0255] According to the preparation method of Synthesis Example 8, h-42 was replaced with an equimolar amount of h-114, and l-100 was replaced with an equimolar amount of n-114 to obtain compound 114 (3.09 g), HPLC purity ≥ 99.91%. Mass spectrometry m / z: 950.4217 (theoretical value: 950.4236). Theoretical elemental content (%) C 71 H 54 N 2 O: C, 89.65; H, 5.72; N, 2.95. Measured elemental content (%): C, 89.70; H, 5.69; N, 2.97.

[0256] Synthesis Example 10: Synthesis of Compound 144

[0257]

[0258] According to the preparation method of Synthesis Example 8, replace j-100 with an equimolar amount of j-144, l-100 with an equimolar amount of l-144, and l-100 with an equimolar amount of n-144 to obtain Compound 144 (3.05 g), HPLC purity ≥ 99.94%. Mass spectrometry m / z: 870.3561 (theoretical value: 870.3548). Theoretical elemental content (%) C 65 H 38 D 4 N 2 O: C, 89.63; H, 5.32; N, 3.22. Measured elemental content (%): C, 89.58; H, 5.36; N, 3.18.

[0259] Synthesis Example 11: Synthesis of Compound 179

[0260]

[0261] Synthesis intermediate h-179

[0262] According to the preparation method of intermediate h-24 in Synthesis Example 3, replace c-24 with an equimolar amount of c-42 and d-24 with an equimolar amount of d-26 to obtain intermediate h-179 (8.68 g), HPLC purity ≥ 99.82%. Mass spectrometry m / z: 531.1373 (theoretical value: 531.1390).

[0263] Synthesis of Compound 179

[0264] According to the preparation method of Synthesis Example 8, replace h-42 with an equimolar amount of h-179, j-100 with an equimolar amount of j-179, l-100 with an equimolar amount of g-24, and l-100 with an equimolar amount of n-179 to obtain Compound 179 (3.01 g), HPLC purity ≥ 99.94%. Mass spectrometry m / z: 871.3623 (theoretical value: 871.3611). Theoretical elemental content (%) C 65 H 37 D 5 N 2 O: C, 89.52; H, 5.43; N, 3.21. Measured elemental content (%): C, 89.49; H, 5.47; N, 3.17.

[0265] Synthesis Example 12: Synthesis of Compound 215

[0266]

[0267] According to the preparation method of Synthesis Example 8, replace j-100 with an equimolar amount of j-215, l-100 with an equimolar amount of n-144, and l-100 with an equimolar amount of n-215 to obtain Compound 215 (3.07 g), HPLC purity ≥ 99.93%. Mass spectrometry m / z: 916.3444 (theoretical value: 916.3454). Theoretical elemental content (%) C 69 H 44 N 2 O: C, 90.36; H, 4.84; N, 3.05. Measured elemental content (%): C, 90.41; H, 4.79; N, 3.11.

[0268] Synthesis Example 13: Synthesis of Compound 244

[0269]

[0270] Synthesis intermediate h-244

[0271] According to the preparation method of intermediate h-24 in Synthesis Example 3, replace f-24 with an equimolar amount of f-42 and g-24 with an equimolar amount of n-144 to obtain intermediate h-244 (9.31 g), HPLC purity ≥ 99.80%. Mass spectrometry m / z: 581.1533 (theoretical value: 581.1546).

[0272] Synthesis of Compound 244

[0273] According to the preparation method of Synthesis Example 8, replace h-42 with an equimolar amount of h-244, j-100 with an equimolar amount of j-244, and l-100 with an equimolar amount of l-144 to obtain Compound 244 (3.11 g), HPLC purity ≥ 99.92%. Mass spectrometry m / z: 942.3619 (theoretical value: 942.3610). Theoretical elemental content (%) C 71 H 46 N 2 O: C, 90.42; H, 4.92; N, 2.97. Measured elemental content (%): C, 90.37; H, 4.89; N, 3.01.

[0274] Synthesis Example 14: Synthesis of Compound 252

[0275]

[0276] Synthesis intermediate h-252

[0277] According to the preparation method of intermediate h-24 in Synthesis Example 3, replace c-24 with an equimolar amount of c-252 and d-24 with an equimolar amount of d-26 to obtain intermediate h-252 (13.23 g), with HPLC purity ≥ 99.81%. Mass spectrometry m / z: 581.1531 (theoretical value: 581.1546).

[0278] Synthesize Compound 252

[0279] According to the preparation method of Synthesis Example 8, replace h-42 with an equimolar amount of h-252 to obtain Compound 252 (3.16 g), with HPLC purity ≥ 99.91%. Mass spectrometry m / z: 942.3624 (theoretical value: 942.3610). Theoretical elemental content (%) C 71 H 46 N 2 O: C, 90.42; H, 4.92; N, 2.97. Measured elemental content (%): C, 90.38; H, 4.87; N, 3.03.

[0280] Synthesis Example 15: Synthesis of Compound 262

[0281]

[0282] Synthesize intermediate h-262

[0283] According to the preparation method of intermediate h-24 in Synthesis Example 3, replace c-24 with an equimolar amount of c-262 to obtain intermediate h-262 (8.93 g), with HPLC purity ≥ 99.81%. Mass spectrometry m / z: 557.1928 (theoretical value: 557.1910).

[0284] Synthesize Compound 262

[0285] According to the preparation method of Synthesis Example 8, replace h-42 with an equimolar amount of h-262, l-100 with an equimolar amount of g-24, and l-100 with an equimolar amount of n-262 to obtain Compound 262 (3.08 g), with HPLC purity ≥ 99.94%. Mass spectrometry m / z: 892.3806 (theoretical value: 892.3817). Theoretical elemental content (%) C 68 H 48 N 2 : C, 91.45; H, 5.42; N, 3.14. Measured elemental content (%): C, 91.51; H, 5.39; N, 3.16.

[0286] Synthesis Example 16: Synthesis of Compound 289

[0287]

[0288] According to the preparation method of Synthesis Example 8, l-100 was replaced with an equimolar amount of n-289 to obtain Compound 289 (3.04 g), with HPLC purity ≥ 99.93%. Mass spectrometry m / z: 906.3260 (theoretical value: 906.3246). Theoretical elemental content (%) C 67 H 42 N 2 O: C, 88.72; H, 4.67; N, 3.09. Measured elemental content (%): C, 88.68; H, 4.68; N, 3.14.

[0289] Synthesis Example 17: Synthesis of Compound 302

[0290]

[0291] Synthesis intermediate h-302

[0292] According to the preparation method of intermediate h-24 in Synthesis Example 3, c-24 was replaced with an equimolar amount of c-302 to obtain intermediate h-302 (12.28 g), with HPLC purity ≥ 99.79%. Mass spectrometry m / z: 547.1150 (theoretical value: 547.1161).

[0293] Synthesis of Compound 302

[0294] According to the preparation method of Synthesis Example 8, h-42 was replaced with an equimolar amount of h-302, l-100 was replaced with an equimolar amount of n-144, and l-100 was replaced with an equimolar amount of n-302 to obtain Compound 302 (3.06 g), with HPLC purity ≥ 99.93%. Mass spectrometry m / z: 912.2649 (theoretical value: 912.2633). Theoretical elemental content (%) C 65 H 40 N 2 S 2 : C, 85.50; H, 4.42; N, 3.07. Measured elemental content (%): C, 85.47; H, 4.39; N, 3.11.

[0295] Synthesis Example 18: Synthesis of Compound 304

[0296]

[0297] According to the preparation method of Synthesis Example 8, l-100 was replaced with an equimolar amount of n-304 to obtain Compound 304 (3.08 g), with HPLC purity ≥ 99.92%. Mass spectrometry m / z: 932.3751 (theoretical value: 932.3767). Theoretical elemental content (%) C 70 H48 N 2 O: C, 90.10; H, 5.18; N, 3.00. Measured elemental content (%): C, 90.05; H, 5.24; N, 2.97.

[0298] Synthesis Example 19: Synthesis of Compound 325

[0299]

[0300] According to the preparation method of Synthesis Example 8, replace j-100 with an equimolar amount of j-179, l-100 with an equimolar amount of l-325, and l-100 with an equimolar amount of n-304 to obtain Compound 325 (3.06 g), HPLC purity ≥ 99.93%. Mass spectrometry m / z: 911.3901 (theoretical value: 911.3924). Theoretical elemental content (%) C 68 H 41 D 5 N 2 O: C, 89.54; H, 5.63; N, 3.07. Measured elemental content (%): C, 89.57; H, 5.58; N, 3.11.

[0301] Synthesis Example 20: Synthesis of Compound 332

[0302]

[0303] Synthesis Intermediate h-332

[0304] According to the preparation method of Intermediate h-24 in Synthesis Example 3, replace c-24 with an equimolar amount of c-332 to obtain Intermediate h-332 (9.73 g), HPLC purity ≥ 99.77%. Mass spectrometry m / z: 607.1714 (theoretical value: 607.1703).

[0305] Synthesis of Compound 332

[0306] According to the preparation method of Synthesis Example 8, replace h-42 with an equimolar amount of h-332, l-100 with an equimolar amount of l-332, and l-100 with an equimolar amount of n-289 to obtain Compound 332 (3.13 g), HPLC purity ≥ 99.90%. Mass spectrometry m / z: 962.3881 (theoretical value: 962.3872). Theoretical elemental content (%) C 71 H 50 N 2 O 2 : C, 88.54; H, 5.23; N, 2.91. Measured elemental content (%): C, 88.59; H, 5.19; N, 2.88.

[0307] Synthesis Example 21: Synthesis of Compound 363

[0308]

[0309] Synthesis Intermediate p-363

[0310] Under argon protection, add c-24 (32.13 g, 92.00 mmol), o-363 (15.36 g, 92.00 mmol), K 2 CO 3 (25.43 g, 184.00 mmol), Pd(PPh 3 ) 4 (1.07 g, 0.92 mmol) and 460 mL of a mixed solvent of toluene / ethanol / water (2:1:1) to the reaction flask, and heat the above system to reflux for 3 h. After the reaction is completed, wait for the reaction mixture to cool to room temperature, filter to obtain a filter cake, wash the filter cake with ethanol, and finally recrystallize the filter cake with toluene / ethanol = 10:1 to obtain Intermediate p-363 (30.61 g, yield 85%), HPLC purity ≥ 99.67%. Mass spectrometry m / z: 391.1227 (theoretical value: 391.1208).

[0311] Synthesis Intermediate q-363

[0312] Under argon protection, add p-363 (25.44 g, 65.00 mmol), PPh 3 (42.59 g, 162.00 mmol) and (130 mL) o-DCB solution to the reaction flask, and heat to reflux with vigorous stirring for 21 h. After the reaction is completed, wait for the reaction mixture to cool to room temperature and concentrate under high vacuum. The crude product is purified by column chromatography on silica gel with hexane / ethyl acetate (9:1) to obtain Intermediate q-363 (12.62 g, yield 54%), HPLC purity ≥ 99.74%. Mass spectrometry m / z: 359.1322 (theoretical value: 359.1310). 1 1H NMR (500 MHz, CDCl3) (δ, ppm): 9.55 (s, 1H), 8.12–8.10 (m, 1H), 7.84 (s, 1H), 7.55 (d, 1H), 7.54 (d, 1H), 7.53–7.51 (m, 1H), 7.40 (d, 1H), 7.35–7.32 (m, 3H), 7.24 (td, 1H), 7.07 (dd, 1H), 6.98 (d, 1H), 6.97 (d, 1H), 1.54 (s, 3H).

[0313] Synthesis Intermediate s-363

[0314] Under argon protection, q-363 (11.50 g, 32.00 mmol), r-363 (6.13 g, 32.00 mmol), Pd(OAc) were added to the reaction bottle. 2 (0.14 g, 0.63 mmol), tri-tert-butylphosphine tetrafluoroborate (0.55 g, 1.89 mmol) and sodium tert-butoxide (7.69 g, 80 mmol) and 270 ml of toluene were added, and the above system was heated to reflux for reaction for 5 h. After the reaction was completed, the reaction mixture was cooled to room temperature, toluene was removed and extracted with dichloromethane and distilled water, and then the solvent was removed in vacuo. The crude product was purified by column chromatography on silica gel with hexane / ethyl acetate (9:1), and finally recrystallized with dichloromethane / hexane to obtain intermediate s-363 (7.82 g, yield 52%). HPLC purity ≥99.81%. Mass spectrum m / z: 469.1245 (theoretical value: 469.1233).

[0315] Synthesis of compound 363

[0316] Under argon protection, s-363 (2.35 g, 5.00 mmol), i-363 (2.17 g, 5.00 mmol), Pd 2 (dba) 3 (0.06g, 0.07mmol), BINAP (0.09g, 0.14mmol), sodium tert-butoxide (0.96g, 10mmol) and 25ml of toluene were heated under reflux for 7h under stirring. After the reaction was completed, it was cooled to room temperature, dichloromethane and distilled water were added to the mixture for extraction, and the mixture was allowed to stand for separation. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The temperature was lowered for crystallization, suction filtered, and finally recrystallized from toluene to obtain compound 363 (3.04g), HPLC purity ≥99.96%. Mass spectrum m / z: 866.4251 (theoretical value: 866.4236). Theoretical element content (%) C 64 H 54 N 2 O: C, 88.65; H, 6.28; N, 3.23. Measured element content (%): C, 88.70; H, 6.31; N, 3.18.

[0317] Synthesis Example 22: Synthesis of Compound 369

[0318]

[0319] According to the preparation method of Synthesis Example 21, c-24 was replaced with an equimolar amount of c-42, and i-363 was replaced with an equimolar amount of i-369 to obtain Compound 369 (2.90 g), with HPLC purity ≥ 99.97%. Mass spectrometry m / z: 816.3151 (theoretical value: 816.3141). Theoretical elemental content (%) C 61 H 40 N 2 O: C, 89.68; H, 4.94; N, 3.43. Measured elemental content (%): C, 89.72; H, 4.97; N, 3.39.

[0320] Synthesis Example 23: Synthesis of Compound 377

[0321]

[0322] According to the preparation method of Synthesis Example 21, q-363 was replaced with an equimolar amount of q-369, r-363 was replaced with an equimolar amount of r-377, and i-363 was replaced with an equimolar amount of i-377 to obtain Compound 377 (3.08 g), with HPLC purity ≥ 99.95%. Mass spectrometry m / z: 892.3440 (theoretical value: 892.3454). Theoretical elemental content (%) C 67 H 44 N 2 O: C, 90.11; H, 4.97; N, 3.14. Measured elemental content (%): C, 90.07; H, 5.02; N, 3.11.

[0323] Synthesis Example 24: Synthesis of Compound 383

[0324]

[0325] According to the preparation method of Synthesis Example 21, s-363 was replaced with an equimolar amount of s-377, and i-363 was replaced with an equimolar amount of i-383 to obtain Compound 383 (3.14 g), with HPLC purity ≥ 99.90%. Mass spectrometry m / z: 966.3602 (theoretical value: 966.3610). Theoretical elemental content (%) C 73 H 46 N 2 O: C, 90.66; H, 4.79; N, 2.90. Measured elemental content (%): C, 90.63; H, 4.85; N, 2.85.

[0326] Synthesis Example 25: Synthesis of Compound 433

[0327]

[0328] According to the preparation method of Synthesis Example 21, q-363 was replaced with an equimolar amount of q-369, r-363 was replaced with an equimolar amount of r-433, and i-363 was replaced with an equimolar amount of i-369 to obtain Compound 433 (3.03 g), with HPLC purity ≥ 99.96%. Mass spectrometry m / z: 866.3311 (theoretical value: 866.3297). Theoretical elemental content (%) C 65 H 42 N 2 O: C, 90.04; H, 4.88; N, 3.23. Measured elemental content (%): C, 90.07; H, 4.92; N, 3.19.

[0329] Synthesis Example 26: Synthesis of Compound 453

[0330]

[0331] According to the preparation method of Synthesis Example 21, c-24 was replaced with an equimolar amount of c-51, r-363 was replaced with an equimolar amount of r-453, and i-363 was replaced with an equimolar amount of i-453 to obtain Compound 453 (3.00 g), with HPLC purity ≥ 99.96%. Mass spectrometry m / z: 856.2928 (theoretical value: 856.2912). Theoretical elemental content (%) C 63 H 40 N 2 S: C, 88.29; H, 4.70; N, 3.27. Measured elemental content (%): C, 88.34; H, 4.66; N, 3.30.

[0332] Synthesis Example 37: Synthesis of Compound 478

[0333]

[0334] According to the preparation method of Synthesis Example 21, q-363 was replaced with an equimolar amount of q-369, r-363 was replaced with an equimolar amount of r-478, and i-363 was replaced with an equimolar amount of i-478 to obtain Compound 478 (3.10 g), with HPLC purity ≥ 99.91%. Mass spectrometry m / z: 952.3471 (theoretical value: 952.3454). Theoretical elemental content (%) C 72 H 44 N 2 O: C, 90.73; H, 4.65; N, 2.94. Measured elemental content (%): C, 90.69; H, 4.70; N, 2.89.

[0335] Synthesis Example 28: Synthesis of Compound 488

[0336]

[0337] According to the preparation method of Synthesis Example 21, c-24 was replaced with an equimolar amount of c-42, o-363 was replaced with an equimolar amount of o-488, and i-363 was replaced with an equimolar amount of i-369 to obtain Compound 488 (3.08 g), with an HPLC purity of ≥99.94%. Mass spectrometry m / z: 892.3434 (theoretical value: 892.3454). Theoretical elemental content (%) C 67 H 44 N 2 O: C, 90.11; H, 4.97; N, 3.14. Measured elemental content (%): C, 90.07; H, 5.02; N, 3.18.

[0338] Synthesis Example 29: Synthesis of Compound 507

[0339]

[0340] According to the preparation method of Synthesis Example 21, c-24 was replaced with an equimolar amount of c-262, and i-363 was replaced with an equimolar amount of i-507 to obtain Compound 507 (2.96 g), with an HPLC purity of ≥99.95%. Mass spectrometry m / z: 856.3467 (theoretical value: 856.3454). Theoretical elemental content (%) C 67 H 44 N 2 O: C, 89.69; H, 5.17; N, 3.27. Measured elemental content (%): C, 89.71; H, 5.21; N, 3.25.

[0341] The organic materials in the device preparation examples were all purified by sublimation, and the purity was above 99.99%. The ITO glass substrates and ITO / Ag / ITO glass substrates used in the device preparation examples were all purchased on the market.

[0342] The following are other compounds used in the device preparation examples except for the carbazole-containing aromatic amine compounds described in the present invention:

[0343]

[0344]

[0345] A combined IVL test system was composed of a test software, a computer, a K2400 digital source meter from Keithley Corporation in the United States, and a PR788 spectral scanning luminance meter from Photo Research Corporation in the United States. At atmospheric pressure and room temperature, the device prepared by the present invention was tested at a current density of 15 mA / cm 2Luminous efficiency, driving voltage, etc. at that time. Using the M6000 OLED lifetime test system of McScience Company, the service life (the brightness decays to 95% of the initial brightness) of the device prepared by the present invention was tested at atmospheric pressure and room temperature. The test results are shown in Tables 1 to 4.

[0346] Comparative device preparation example 1: Comparative device 1

[0347] First, the ITO glass substrate was ultrasonically cleaned with deionized water twice for 20 minutes each time, then ultrasonically cleaned with isopropanol, acetone, and methanol for 20 minutes each in turn, then exposed to ultraviolet light and ozone for 30 minutes, and finally placed in a vacuum evaporation device for standby.

[0348] The following layers were sequentially evaporated on the above ITO glass substrate: a. 2-TNATA as a hole injection layer with a thickness of 60 nm; b. HT-1 as a hole transport layer with a thickness of 35 nm; c. TBADN and BD (mass ratio 97:3) as a light-emitting layer with a thickness of 30 nm; d. TPBi as a hole blocking layer with a thickness of 25 nm; e. NBphen and Liq (mass ratio 5:2) as an electron transport layer with a thickness of 30 nm; f. LiF as an electron injection layer with a thickness of 0.2 nm; g. Al as a cathode with a thickness of 110 nm.

[0349] Comparative device preparation example 2: Comparative device 2

[0350] Replace HT-1 in the hole transport layer with HT-2, and the other steps are the same as those in Comparative device preparation example 1, then Comparative device 2 can be obtained.

[0351] Device preparation examples 1 to 27: Light-emitting devices 1 to 27

[0352] Replace HT-1 in the hole transport layer with the carbazole-containing aromatic amine compound described in the present invention in Synthesis examples 3 to 29 in turn, and the other steps are the same as those in Comparative device preparation example 1, then devices 1 to 27 can be obtained.

[0353] Table 1

[0354]

[0355]

[0356] Comparative device preparation example 3: Comparative device 3

[0357] First, the ITO / Ag / ITO glass substrate was ultrasonically cleaned with deionized water twice for 20 minutes each time, then ultrasonically cleaned with isopropanol, acetone, and methanol for 20 minutes each in turn, then exposed to ultraviolet light and ozone for 30 minutes, and finally placed in a vacuum evaporation device for standby.

[0358] On the above ITO / Ag / ITO glass substrate, each organic layer and the cathode are sequentially evaporated, specifically: a. HTM-1 and p-1 (mass ratio 100:5) are used as the hole injection layer with a thickness of 20 nm; b. HTM-1 is used as the hole transport layer with a thickness of 40 nm; c. HT-1, RH, and RD (mass ratio 48:48:4) are used as the light-emitting layer with a thickness of 35 nm; d. NBphen and Liq (mass ratio 3:1) are used as the electron transport layer with a thickness of 30 nm; e. LiF is used as the electron injection layer with a thickness of 0.2 nm; f. Mg and Ag (mass ratio 1:9) are used as the cathode with a thickness of 10 nm; g. CP-4 is used as the covering layer with a thickness of 100 nm.

[0359] Comparative device preparation example 4: Comparative device 4

[0360] Replace HT-1 in the light-emitting layer with HT-2, and the other steps are the same as those in comparative device preparation example 3, then comparative device 4 can be obtained.

[0361] Device preparation examples 28 - 54: Light-emitting devices 28 - 54

[0362] Replace HT-1 in the light-emitting layer with the carbazole-containing aromatic amine compound of the present invention in synthesis examples 3 - 29 in sequence, and the other steps are the same as those in comparative device preparation example 3, then devices 28 - 54 can be obtained.

[0363] Table 2

[0364]

[0365]

[0366] Comparative device preparation example 5: Comparative device 5

[0367] First, ultrasonically clean the ITO / Ag / ITO glass substrate with deionized water twice for 20 minutes each time, then ultrasonically clean it with isopropanol, acetone, and methanol for 20 minutes each in sequence, then expose it to ultraviolet light and ozone for 30 minutes, and finally put it into a vacuum evaporation equipment for standby.

[0368] On the above ITO / Ag / ITO glass substrate, the following layers are sequentially evaporated: a. HTM-1 and p-1 (mass ratio 100:5) are used as the hole injection layer with a thickness of 20 nm; b. HTM-1 is used as the hole transport layer with a thickness of 35 nm; c. HT-1, GH, and Ir(mppy) 3(Mass ratio 64:32:4) is used as the light-emitting layer with a thickness of 35 nm; d, NBphen and Liq (mass ratio 3:1) are used as the electron transport layer with a thickness of 30 nm; e, LiF is used as the electron injection layer with a thickness of 0.2 nm; f, Mg and Ag (mass ratio 1:9) are used as the cathode with a thickness of 10 nm; g: CP-4 is used as the cover layer with a thickness of 100 nm.

[0369] Comparative device preparation example 6: Comparative device 6

[0370] Replace HT-1 in the light-emitting layer with HT-2, and keep other steps the same as those in Comparative device preparation example 5, then Comparative device 6 can be obtained.

[0371] Device preparation examples 55 to 81: Light-emitting devices 55 to 81

[0372] Replace HT-1 in the light-emitting layer with the carbazole-containing aromatic amine compound described in the present invention in Synthesis examples 3 to 29 in sequence, and keep other steps the same as those in Comparative device preparation example 5, then Devices 55 to 81 can be obtained.

[0373] Table 3

[0374]

[0375]

[0376] Comparative device preparation example 7: Comparative device 7

[0377] First, ultrasonically clean the ITO / Ag / ITO glass substrate with deionized water twice for 20 minutes each time, then ultrasonically clean it with isopropanol, acetone and methanol for 20 minutes each in sequence, then expose it to ultraviolet light and ozone for 30 minutes, and finally put it into the vacuum evaporation equipment for standby.

[0378] Deposit the following layers layer by layer on the above ITO / Ag / ITO glass substrate: a, 2-TNATA is used as the hole injection layer with a thickness of 60 nm; b, HTM-1 is used as the hole transport layer with a thickness of 40 nm; c, HOST, GH and Ir(mppy) 3 (Mass ratio 64:32:4) is used as the light-emitting layer with a thickness of 35 nm; d, NBphen and Liq (mass ratio 5:3) are used as the electron transport layer with a thickness of 35 nm; e, LiF is used as the electron injection layer with a thickness of 0.2 nm; f, Mg and Ag (mass ratio 1:9) are used as the cathode with a thickness of 12 nm; g: CP-1 is used as the cover layer with a thickness of 100 nm.

[0379] Device preparation examples 82 to 108: Light-emitting devices 82 to 108

[0380] Replace HT-1 in the light-emitting layer with the carbazole-containing aromatic amine compound of the present invention in Synthesis Examples 3 to 29 in sequence, and the other steps are the same as those in Comparative Device Preparation Example 5, then Devices 55 to 81 can be obtained.

[0381] Table 4

[0382]

[0383]

[0384] The device data in Tables 1 to 4 show that when the carbazole-containing aromatic amine compound of the present invention is used as the hole transport layer, the host material of the light-emitting layer and the covering layer, the driving voltage, the luminous efficiency and the service life of the device are all significantly improved, indicating that the carbazole-containing aromatic amine compound of the present invention is a class of OLED materials with excellent performance and has good application prospects.

[0385] It should be noted that the present invention has been specifically described with individual embodiments, but without departing from the principle of the present invention, those of ordinary skill in the art can make various improvements in form or details to the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. An aromatic amine compound containing carbazole, having a structure represented by formula (I-A) or formula (I-B): Wherein, The described Ar 1 , Ar 2 is independently selected from one of the structures shown below: Among them, the a 2 is selected from 0, 1, 2, 3, 4 or 5, and the b 2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, and the c 2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, and the d 2 is selected from 0, 1, 2 or 3, and the e 2 is selected from 0, 1, 2, 3 or 4; the f 2 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; The described R 2 Each occurrence is independently selected from H, D, a linear or branched C1-C4 alkyl group which may or may not be deuterium-substituted, a C3-C10 cycloalkyl group which may or may not be deuterium-substituted, and a phenyl group which may or may not be deuterium-substituted; The described R 4 ~R 6 is independently selected from one of deuterium-substituted or unsubstituted C1-C4 linear or branched alkyl groups and deuterium-substituted or unsubstituted C6-C10 aryl groups; The described L 1 ~L 2 are independently selected from a single bond or one of the structures shown below: The described L 3 selected from a single bond or one of the structures shown below: The described L 4 selected from one of the structures shown below: wherein, said a 21 is, each time it appears, independently selected from 0, 1, 2, 3 or 4; said b 21 is, each time it appears, independently selected from 0, 1, 2, 3, 4, 5 or 6; said c 21 is, each time it appears, independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; Said R 21 each occurrence is independently selected from H, D, and a linear or branched C1-C4 alkyl group that is either deuterium-substituted or unsubstituted; In formula (I-A), A and B independently are selected from the structure represented by formula (i-a); in formula (I-B), A is selected from the structure represented by formula (i-a), and B is selected from formula (i-d): Among them, the represents the connection with L’ or L 3 , and the "---" represents the fused bond with the five-membered N-containing heterocycle; The described a 1 Each occurrence is independently selected from 0, 1, 2 or 3; the described c 1 Each occurrence is independently selected from 0, 1, 2, 3 or 4; Said R 1 Each occurrence is independently selected from one of H and D, which may be the same or different; R is selected from a substituted or unsubstituted C6-C12 aryl group; the "substituted or unsubstituted" in the "substituted or unsubstituted C6-C12 aryl group" means not being substituted or being substituted by one or more substituents selected from the group consisting of: deuterium atom, deuterium-substituted or unsubstituted C1-C6 alkyl group; L’ is selected from a single bond; R’ is selected from one of a deuterium-substituted or unsubstituted C1-C4 straight-chain or branched-chain alkyl group, a substituted or unsubstituted C6-C12 aryl group; the "substituted or unsubstituted" in the "substituted or unsubstituted C6-C12 aryl group" means not being substituted or being substituted by one or more substituents selected from the group consisting of: deuterium atom, deuterium-substituted or unsubstituted C1-C6 alkyl group; The described X is selected from one of O, S or CR 3 ’R 4 ’, and one of the described R 3 ’ and R 4 ’ are independently selected from deuterium-substituted or unsubstituted C1-C4 linear or branched alkyl groups; The described a 1 ’, b 1 ’ are independently selected from 0, 1, 2 or 3; The described R 1 ’, R 2 ’ is, each time it appears, independently selected from the group consisting of H, D, a linear or branched C1-C4 alkyl group which may or may not be deuterium-substituted, and a phenyl group which may or may not be deuterium-substituted.

2. The aromatic amine compound containing carbazole according to claim 1, characterized in that, The described Ar 1 , Ar 2 is independently selected from one of the structures shown below: The described R 2 Each occurrence is independently selected from one of H and D; The described R 4 ~R 6 is independently selected from one of deuterium-substituted or unsubstituted C1 alkyl and deuterium-substituted or unsubstituted C6 aryl.

3. The aromatic amine compound containing carbazole according to claim 1, characterized in that, The described L 4 selected from one of the structures shown below: The described R 21 Each occurrence is independently selected from one of H and D, which may be the same or different.

4. The aromatic amine compound containing carbazole according to claim 1, characterized in that, The described selected from the structures shown below: Among them, the said R, R 1 , a 1 , b 1 are all as described in claim 1.

5. The aromatic amine compound containing carbazole according to claim 1, characterized in that, The described selected from one of the structures shown below: Among them, the said a 1 ', b 1 ' are all as described in claim 1; The described R 11 ’, R 12 ’, each time it appears, is independently selected from H, D, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, tert-butyl, deuterated tert-butyl, or one of the structures shown below: The described R 13 ’, R 14 ’ are independently selected from methyl, deuterated methyl, ethyl; The described R 15 ' is selected from methyl or one of the following structures: wherein, the said a 11 each occurrence is independently selected from 0, 1, 2, 3, 4 or 5; the said b 11 each occurrence is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; Said R 11 Each occurrence is independently selected from one of H and D, which can be the same or different. The described L 11 ' is selected from a single bond.

6. The aromatic amine compound containing carbazole according to claim 1, characterized in that, the aromatic amine compound containing carbazole has any one of the following general formulas (II-A) to (II-F): Among them, the described Ar 1 、Ar 2 、R、R 1 、a 1 as described in claim 1; The described L 1 to L 4 as described in claim 3; The described a 1 ’, b 1 ’, R 11 ’, R 12 ’, R 13 ’, R 14 ’, R 15 ’, L 11 ’ are all as described in claim 5.

7. An aromatic amine compound containing carbazole, characterized in that, the aromatic amine compound containing carbazole is selected from one of the following compounds:

8. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer between the anode and the cathode, and the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, characterized in that, the organic layer contains one or more of the aromatic amine compounds containing carbazole according to any one of claims 1-7.

9. An organic electroluminescent device, comprising an anode, a cathode, an organic layer between the anode and the cathode, and a covering layer on the side of the cathode facing away from the anode, and the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, characterized in that, the organic layer contains one or more of the aromatic amine compounds containing carbazole according to any one of claims 1-7.

10. An organic electroluminescent device, comprising an anode, a cathode, an organic layer between the anode and the cathode, and a covering layer on the side of the cathode facing away from the anode, and the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, characterized in that, the covering layer contains one or more of the aromatic amine compounds containing carbazole according to any one of claims 1-7.

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