Carbazole indole derivative and organic electroluminescent device thereof

Abstract

The present invention relates to the technical field of organic optoelectronic materials, and more specifically to a carbazole indole derivative and an organic electroluminescent device thereof. The carbazole indole derivative provided by the present invention has appropriate HOMO and LUMO properties. When used as a host material for a light-emitting layer, it can effectively transfer energy to a guest material. It also has appropriate charge transfer properties, thereby improving the injection efficiency of holes and electrons into the light-emitting layer, thereby increasing the generation rate of excitons in the light-emitting layer, thereby reducing the driving voltage of the device and improving the luminous efficiency of the device. Because the material has appropriate HOMO and LUMO properties, it can be well matched with other organic functional layers, improving the interfacial transfer efficiency of charges and the interfacial stability with adjacent organic functional layers. The material itself also has excellent thermal and chemical stability, which can delay device aging and thus increase the service life of the device.

Description

Technical Field

[0001] The present invention relates to the technical field of organic photoelectric materials, and in particular to a carbazole indole derivative and an organic electroluminescent device thereof. Background Art

[0002] Organic Light-Emitting Diode (OLED) has the characteristics of light weight, wide viewing angle, fast response speed, wide operating temperature range, low energy consumption, high efficiency, good color purity, high clarity, and good flexibility. It has been widely used in the lighting and display fields and is considered by the industry to be one of the most promising display and lighting technologies.

[0003] The classic OLED device has a "sandwich" structure, with a light-emitting layer sandwiched between the cathode and anode electrodes. The light-emitting layer contains a light-emitting substance (guest material). A certain operating voltage is applied between the two electrodes, causing holes and electrons to be injected from the anode and cathode respectively. Then, they reach the light-emitting layer, recombine to produce excitons, and release energy. Under the action of the electric field, the excitons migrate and transfer the energy to the light-emitting substance. The electrons in the molecules of the light-emitting substance jump from the ground state to the excited state. Because the excited state is unstable, the electrons migrate back from the excited state to the ground state, thereby releasing energy in the form of light and generating luminescence. Generally speaking, the lowest unoccupied molecular orbital (LUMO) of the host material is higher than that of the guest material, and the highest occupied molecular orbital (HOMO) of the host material is lower than that of the guest material. In order to improve the performance of the device, more organic functional layers are provided between the anode and the light-emitting layer, and between the cathode and the light-emitting layer. Generally, the hole transport region is between the anode and the light-emitting layer, which mainly plays the role of injecting and transporting holes, including the hole injection layer, hole transport layer, light-emitting auxiliary layer, electron blocking layer, etc.; the electron transport region is between the cathode and the light-emitting layer, which mainly plays the role of injecting and transporting electrons, including the electron injection layer, electron transport layer, hole blocking layer, etc.

[0004] In addition to the organic functional layer between the anode and cathode, a cover layer is also placed on the outside of the light-emitting electrode (away from the non-light-emitting electrode). Generally, the cover layer has a high refractive index, which can improve the device's light transmittance and redirect light, thereby improving the device's luminous efficiency and color purity.

[0005] In order to further improve the luminous efficiency, color purity and service life of OLED devices, it is necessary to develop a host material with high energy level matching with the guest material and the adjacent organic functional layer, appropriate charge transfer performance and excellent stability. Summary of the Invention

[0006] To solve the above technical problems, the present invention provides a carbazole indole derivative having appropriate charge mobility, appropriate HOMO and T1 values, and excellent thermal and chemical stability. When used as a host material in an OLED device, it can improve the luminous efficiency and service life of the OLED device. The carbazole indole derivative has a structure in which the groups represented by formula (IA) and formula (IB) are combined:

[0007]

[0008] Wherein, two adjacent X1 to X8 in formula (IA) are carbon atoms and are combined with two "*" in formula (IB), and the rest are independently selected from nitrogen atoms or C-L1-R1, and the X9 to X8 are carbon atoms. 12 Independently selected from nitrogen atom or C-L1-R1;

[0009] Ar1 and Ar2 are independently selected from a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a substituted or unsubstituted C2-C30 heteroaryl group, or a group represented by formula (IC), and at least one of Ar1 and Ar2 is selected from a group represented by formula (IC):

[0010]

[0011] wherein each occurrence of Y is the same or different and is selected from one of oxygen atom, sulfur atom, N-L4-R2, and CR3R4; each occurrence of R2 is the same or different and is selected from one of bond, substituted or unsubstituted C6-C30 aryl group, monovalent group formed by fusion of substituted or unsubstituted C6-C30 aromatic ring and substituted or unsubstituted C3-C7 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C6-C30 arylene group, divalent group formed by fusion of substituted or unsubstituted C6-C30 aromatic ring and substituted or unsubstituted C3-C7 aliphatic ring, and substituted or unsubstituted C2-C30 heteroarylene group; each occurrence of R3 and R4 is the same or different and is selected from one of bond, hydrogen atom, deuterium atom, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C6-C30 aryl group, , a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C2-C30 heteroarylene group, or The R3 and R4 can be linked to form a substituted or unsubstituted C5-C10 aliphatic ring; when R2, R3 or R4 is selected from a bond, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C2-C30 heteroarylene group, R2, R3 or R4 is linked to L2 or L3;

[0012] Said Y1 to Y8 are independently selected from nitrogen atom or C-L5-R5;

[0013] The R1 and R5, when they appear each time, are the same or different and are selected from one of hydrogen atom, deuterium atom, halogen atom, cyano group, nitro group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, monovalent group formed by fusion of substituted or unsubstituted C6-C30 aromatic ring and substituted or unsubstituted C3-C7 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted silyl group, substituted or unsubstituted amino group, and two adjacent R1 or two adjacent R5 are the same or different. R5 can be linked to form a substituted or unsubstituted C5-C7 aliphatic ring, a substituted or unsubstituted C6-C14 aromatic ring, or a substituted or unsubstituted C2-C10 heteroaromatic ring, and at least two adjacent R1s are linked to form a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted isoquinoline ring, a substituted or unsubstituted quinoxaline ring, or a substituted or unsubstituted quinazoline ring;

[0014] Each occurrence of L1 to L5 is identical or different and is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C4-C30 heteroarylene group;

[0015] Provided that the molecule contains at least one of the following groups: wherein said Z is selected from carbon atom or silicon atom, said Ar 101 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C4-C30 heteroarylene group, wherein Ar 102 ~Ar 104 is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C2-C30 heteroaryl group, and the Ar 102 ~Ar 104 At least one of the following is selected from a substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a substituted or unsubstituted C2-C30 heteroaryl group.

[0016] The present invention also provides an organic electroluminescent device comprising an anode, a cathode and an organic layer, wherein the organic layer comprises a hole transport region between the anode and the cathode, a light-emitting layer, an electron transport region and at least one of a covering layer on the side of the cathode facing away from the anode, and the organic layer contains one or more of the carbazole and indole derivatives described in the present invention.

[0017] Beneficial effects:

[0018] The carbazole indole derivative provided by the present invention has appropriate HOMO and LUMO moieties. When used as the host material of the light-emitting layer, it can effectively transfer energy to the guest material. It also has appropriate charge transport properties, which improves the injection efficiency of holes and electrons into the light-emitting layer, thereby increasing the generation rate of excitons in the light-emitting layer, thereby reducing the driving voltage of the device and improving the luminous efficiency of the device. Due to the appropriate HOMO and LUMO moieties, the material can be well matched with other organic functional layers, improving the interfacial transfer efficiency of charge and the interfacial stability with adjacent organic functional layers. The material itself also has excellent thermal and chemical stability, which can delay device aging and thus increase the service life of the device. DETAILED DESCRIPTION

[0019] The following will be a clear and complete description of the technical solutions of the specific embodiments of the present invention. Obviously, the embodiments described are only part of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without making any creative efforts shall fall within the scope of protection of the present invention.

[0020] In the compounds of the present invention, any atom not designated as a specific isotope is included as any stable isotope of that atom, and includes atoms at both their natural isotopic abundance and unnatural abundance. Taking hydrogen as an example, all naturally occurring compounds contain approximately 0.0156 atomic % deuterium per hydrogen atom.

[0021] As used herein, the use of "H" and "hydrogen atom" means that the hydrogen atoms in a chemical structure contain no more than natural abundance of deuterium atoms or tritium atoms, for example, no more than 0.0156 atomic % of deuterium. "D" and "deuterium atom" mean that the abundance of deuterium content is above natural abundance, for example, any value exceeding 0.1 atomic %, exceeding 1 atomic %, or exceeding 10 atomic %, for example, wherein about 95 atomic % is deuterium. "T" and "tritium atom" mean that the abundance of tritium content is above natural abundance, for example, any value exceeding 0.1 atomic %, exceeding 1 atomic %, or exceeding 10 atomic %, for example, wherein about 95 atomic % is tritium. As used herein, the omitted hydrogen represents "H" or "hydrogen atom".

[0022] The halogen atom mentioned in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0023] The "silyl group" mentioned in the present invention refers to a -SiH3 group, and the "substituted or unsubstituted silyl group" mentioned herein refers to a group in which one or more H groups on the silyl group are substituted or unsubstituted by a substituent.

[0024] The alkyl group described in the present invention refers to a hydrocarbon group formed by missing 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 group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto; the branched-chain alkyl group includes 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 is not limited thereto. The above-mentioned alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.

[0025] The cycloalkyl group described herein refers to a hydrocarbon group formed by removing a 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 include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, and norbornane. Preferred cycloalkyl groups include cyclopentane, cyclohexane, 1-adamantane, 2-adamantane, and norbornane.

[0026] The cycloalkenyl group herein refers to a hydrocarbon group formed by removing a 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 include, but are not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl. The cycloalkyl group is preferably cyclopentenyl or cyclohexenyl.

[0027] The heterocycloalkyl group described herein refers to a group formed by removing a hydrogen atom from a heterocyclic molecule containing at least one heteroatom in addition to carbon atoms. Heteroatoms include nitrogen, oxygen, sulfur, silicon, selenium, and phosphorus atoms, with nitrogen, oxygen, and sulfur atoms being preferred. 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 include, but are not limited to, oxiranyl, thioranyl, propidinyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, and piperazinyl. Preferred heterocyclic groups are tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, and piperazinyl.

[0028] The aryl group described in the present invention refers to a general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon nucleus of an aromatic compound molecule. It can be a monocyclic aromatic group, a polycyclic aromatic group, a condensed aromatic group, or a condensed group of an aromatic group and an aliphatic ring, 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 aromatic group refers to an aromatic group having only one aromatic ring in the molecule, for example, phenyl, etc., but not limited thereto; the polycyclic aromatic group refers to an aromatic group containing two or more independent aromatic rings in the molecule, for example, biphenyl, terphenyl, etc., but not limited thereto; the fused-ring aromatic group refers to an aromatic group containing two or more aromatic rings in the molecule and fused to each other by sharing two adjacent carbon atoms, for example, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylene, fluoranthenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, etc., but not limited thereto. The above-mentioned 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.

[0029] The heteroaryl group described in the present invention refers to a general term for a group in which one or more aromatic carbon atoms in an aromatic group are replaced by a heteroatom, wherein the heteroatom includes but is not limited to oxygen, sulfur, nitrogen, silicon, selenium 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 attachment site of the heteroaryl group may be located on a ring-forming carbon atom or a ring-forming nitrogen atom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a condensed-ring heteroaryl group. The monocyclic heteroaryl groups include, but are not limited to, pyridyl, pyrimidinyl, triazine, furyl, thienyl, pyrrolyl, imidazolyl, etc.; the polycyclic heteroaryl groups include, but are not limited to, bipyridyl, bipyrimidinyl, phenylpyridyl, etc.; the fused-ring heteroaryl groups include, but are not limited to, quinolyl, isoquinolyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, etc., but are not limited to. The above-mentioned heteroaryl group is preferably pyridyl, pyrimidinyl, thienyl, furyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, benzodibenzothienyl, benzodibenzofuranyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, or phenoxathiyl.

[0030] The group formed by the fusion of an aromatic ring and an aliphatic ring of the present invention refers to a general term for a monovalent group formed by removing a hydrogen atom from an aromatic ring and an aliphatic ring (cycloalkyl, cycloalkenyl, cycloalkynyl) fused together. The aromatic ring preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, most preferably 6 to 12 carbon atoms, and may include benzene, naphthalene, anthracene, phenanthrene, etc., but is not limited thereto; the aliphatic ring preferably has 3 to 9 carbon atoms, more preferably 5 to 7 carbon atoms, and may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclopropyne, cyclobutyne, cyclopentyne, cyclohexyne, and cycloheptyne. Preferably, examples of the group formed by the condensation of an aromatic ring and an aliphatic ring may include, but are not limited to, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, and the like.

[0031] The arylene group in the present invention means an aryl group having two bonding sites, that is, a divalent group. The description of the aryl group provided above can be applied thereto, except that the arylene group is a divalent group.

[0032] The heteroarylene group in the present invention means a heteroaryl group having two bonding sites, that is, a divalent group. The description of the heteroaryl group provided above can be applied thereto, except that the heteroarylene group is a divalent group.

[0033] The divalent group formed by the fusion of an aromatic ring and an aliphatic ring described herein refers to a group formed by the fusion of an aromatic ring and an aliphatic ring having two bonding sites, i.e., a divalent group. The description of the group formed by the fusion of an aromatic ring and an aliphatic ring provided above applies, except that the divalent group formed by the fusion of an aromatic ring and an aliphatic ring is a divalent group.

[0034] The term "substituted" as used herein means that a hydrogen atom in a certain functional group is replaced by another atom or functional group (i.e., a substituent), and the position of the substitution is not limited as long as the position is the position where the hydrogen atom is replaced, and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0035] The "substituted or unsubstituted" in the present invention means not substituted or substituted by 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 heterocycloalkyl 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 substituted or unsubstituted silyl group, preferably a deuterium atom, a halogen atom, a cyano group, a nitro group, a C1-C12 alkyl group, a C3-C12 cycloalkyl group, C3-C12 cycloalkenyl, C3-C12 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, substituted or unsubstituted silyl, when substituted by multiple substituents, the multiple substituents are the same or different from each other; preferably, it means not substituted or substituted by one or more substituents selected from the group consisting of: deuterium atom, fluorine atom, cyano group, methyl, trifluoromethyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, deuterated cyclopropane, cyclobutane, methyl-substituted cyclobutane, ethyl-substituted cyclobutane, deuterated Cyclobutanyl, cyclopentanyl, methyl-substituted cyclopentanyl, ethyl-substituted cyclopentanyl, deuterated cyclopentanyl, cyclohexanyl, methyl-substituted cyclohexanyl, ethyl-substituted cyclohexanyl, n-propyl-substituted cyclohexanyl, n-butyl-substituted cyclohexanyl, cyclohexane-substituted cyclohexanyl, deuterated cyclohexanyl, cycloheptyl, cyclopentenyl, methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazine The alkyl radicals include 1,2-dimethyl-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1,2-difluoro-1

[0036] In this specification, when the position of a substituent or a connection site on a ring is not fixed, it means that it can be connected to any of the optional sites of the ring. For example, Can be represented Can be represented Can be represented And so on.

[0037] In this specification, when a substituent or a bond at a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically any of the corresponding optional sites of the ring. For example, Can be represented Can be represented Can be represented And so on.

[0038] The linked ring structures (e.g., saturated or unsaturated C3-C10 carbocycles, substituted or unsubstituted saturated or unsaturated C3-C6 carbocycles) mentioned in the present invention refer to groups connected to each other by chemical bonds, optionally forming double bonds / triple bonds, and may constitute aromatic groups, as shown in the following examples:

[0039]

[0040] In the present invention, the ring formed by connection can be an aromatic ring system, an aliphatic ring system or a ring system formed by the fusion of the two. The ring formed by connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a spiro ring or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentane acene, cyclohexene, cyclohexane, cyclohexane acene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.

[0041] In this specification, "at least one" includes one, two, three, four, five, six, seven, eight or more.

[0042] The present invention provides a carbazole indole derivative having a structure in which the groups represented by formula (IA) and formula (IB) are combined:

[0043]

[0044] Wherein, two adjacent X1 to X8 in formula (IA) are carbon atoms and are combined with two "*" in formula (IB), and the rest are independently selected from nitrogen atoms or C-L1-R1, and the X9 to X8 are carbon atoms. 12Independently selected from nitrogen atom or C-L1-R1;

[0045] Ar1 and Ar2 are independently selected from a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a substituted or unsubstituted C2-C30 heteroaryl group, or a group represented by formula (IC), and at least one of Ar1 and Ar2 is selected from a group represented by formula (IC):

[0046]

[0047] wherein each occurrence of Y is the same or different and is selected from one of oxygen atom, sulfur atom, N-L4-R2, and CR3R4; each occurrence of R2 is the same or different and is selected from one of bond, substituted or unsubstituted C6-C30 aryl group, monovalent group formed by fusion of substituted or unsubstituted C6-C30 aromatic ring and substituted or unsubstituted C3-C7 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C6-C30 arylene group, divalent group formed by fusion of substituted or unsubstituted C6-C30 aromatic ring and substituted or unsubstituted C3-C7 aliphatic ring, and substituted or unsubstituted C2-C30 heteroarylene group; each occurrence of R3 and R4 is the same or different and is selected from one of bond, hydrogen atom, deuterium atom, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C6-C30 aryl group, , a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C2-C30 heteroarylene group, or The R3 and R4 can be linked to form a substituted or unsubstituted C5-C10 aliphatic ring; when R2, R3 or R4 is selected from a bond, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C2-C30 heteroarylene group, R2, R3 or R4 is linked to L2 or L3;

[0048] Said Y1 to Y8 are independently selected from nitrogen atom or C-L5-R5;

[0049] The R1 and R5, when they appear each time, are the same or different and are selected from one of hydrogen atom, deuterium atom, halogen atom, cyano group, nitro group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, monovalent group formed by fusion of substituted or unsubstituted C6-C30 aromatic ring and substituted or unsubstituted C3-C7 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted silyl group, substituted or unsubstituted amino group, and two adjacent R1 or two adjacent R5 are the same or different. R5 can be linked to form a substituted or unsubstituted C5-C7 aliphatic ring, a substituted or unsubstituted C6-C14 aromatic ring, or a substituted or unsubstituted C2-C10 heteroaromatic ring, and at least two adjacent R1s are linked to form a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted isoquinoline ring, a substituted or unsubstituted quinoxaline ring, or a substituted or unsubstituted quinazoline ring;

[0050] Each occurrence of L1 to L5 is identical or different and is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C4-C30 heteroarylene group;

[0051] Provided that the molecule contains at least one of the following groups: wherein said Z is selected from carbon atom or silicon atom, said Ar 101 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C4-C30 heteroarylene group, wherein Ar 102 ~Ar 104 is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C2-C30 heteroaryl group, and the Ar 102 ~Ar 104 At least one of the following is selected from a substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a substituted or unsubstituted C2-C30 heteroaryl group.

[0052] Preferably, at least one of Ar1, Ar2, R1, and R5 contains the following group: wherein said Z is selected from carbon atom or silicon atom, said Ar 101 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C4-C30 heteroarylene group, wherein Ar 102 ~Ar 104 is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C2-C30 heteroaryl group, and the Ar 102 ~Ar 104 At least one of the following is selected from a substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a substituted or unsubstituted C2-C30 heteroaryl group.

[0053] Preferably, the substituent in the "substituted or unsubstituted" is selected from the group consisting of a deuterium atom; a halogen atom; a cyano group; a C1-C12 straight or branched alkyl group substituted or unsubstituted by one or more of the group consisting of a deuterium atom, a halogen atom, a cyano group, 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 methyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a halogen-substituted phenyl group, a cyano-substituted phenyl group, an adamantyl-substituted phenyl group, a norbornyl-substituted phenyl group, a naphthyl group, a deuterated naphthyl group, an anthracenyl group, a phenanthrenyl group, a biphenyl group, a pyridyl group, a pyrimidyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; a deuterium atom; a cyano group; a methyl group; an ethyl group; a methyl group; an ethyl group; a methyl group; an ethyl group; a methyl group; an ethyl group; a methyl group; an ethyl group; a methyl group; a ... a C3-C12 cycloalkyl group which is unsubstituted or substituted by one or more of the group consisting of a deuterium atom, a halogen atom, a cyano group, 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 naphthyl group, and a biphenyl group; a C3-C12 cycloalkenyl group which is unsubstituted or substituted by one or more of the group consisting of a deuterium atom, a halogen atom, a cyano group, 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 naphthyl group, and a biphenyl group; a C6-C30 cycloalkenyl group which is unsubstituted or substituted by one or more of the group consisting of a deuterium atom, a halogen atom, a cyano group, 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 naphthyl group, and a biphenyl group substituted or unsubstituted C2-C30 heteroaryl groups selected from the group consisting of deuterium atoms, halogen atoms, cyano groups, methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, tert-butyl groups, phenyl groups, naphthyl groups, and biphenyl groups; substituted or unsubstituted C6-C30 aromatic rings selected from the group consisting of deuterium atoms, halogen atoms, cyano groups, methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, tert-butyl groups, phenyl groups, naphthyl groups, and biphenyl groups; substituted or unsubstituted C3-C7 aliphatic rings selected from the group consisting of deuterium atoms, halogen atoms, cyano groups, methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, tert-butyl groups, phenyl groups, naphthyl groups, and biphenyl groups; The present invention relates to a substituted or unsubstituted silyl group selected from the group consisting of a phenyl group, a deuterated phenyl group, a methyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a halogen-substituted phenyl group, a cyano-substituted phenyl group, an adamantyl-substituted phenyl group, a norbornyl-substituted phenyl group, a naphthyl group, a deuterated naphthyl group, an anthracenyl group, a phenanthrenyl group, a biphenyl group, a pyridyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group. The substituents are one or more. When there are multiple substituents, the multiple substituents are the same or different. When there are multiple substituents, two adjacent substituents can be connected to form a substituted or unsubstituted saturated or unsaturated C3-C7 carbocyclic ring.

[0054] Preferably, the substituent in the "substituted or unsubstituted" is selected from the group consisting of a deuterium atom; a fluorine atom; a cyano group; one or more substituted or unsubstituted methyl groups selected from the group consisting of a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a phenyl group, a deuterated phenyl group, a methyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a halogen-substituted phenyl group, a cyano-substituted phenyl group, an adamantyl-substituted phenyl group, a norbornyl-substituted phenyl group, a naphthyl group, a deuterated naphthyl group, an anthracenyl group, a phenanthrenyl group, a biphenyl group, a pyridyl group, a pyrimidyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; an ethyl group; an n-propyl group; an isopropyl group; an n-butyl group; a sec-butyl group; an isobutyl group; a tert-butyl group; a deuterated methyl group; a deuterated isopropyl group; a deuterated tert-butyl group; a deuterated methyl group; an ethyl group; an isopropyl group; an n-butyl group; a tert-butyl group; a deuterated ... substituted or unsubstituted cyclopropanyl by one or more selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, and a biphenyl group; substituted or unsubstituted cyclobutanyl by one or more selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, and a biphenyl group; substituted or unsubstituted cyclopentanyl by one or more selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, and a biphenyl group; substituted or unsubstituted cyclohexanyl by one or more selected from the group consisting of a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, and a biphenyl group; substituted or unsubstituted cyclopropanyl by one or more selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, and a biphenyl group; alkenyl; cyclobutenyl substituted or unsubstituted by one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, and a biphenyl group; cyclopentenyl substituted or unsubstituted by one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, and a biphenyl group; cyclohexenyl substituted or unsubstituted by one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, and a biphenyl group; adamantyl substituted or unsubstituted by one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, and a biphenyl group; a norbornyl group which is unsubstituted or substituted by one or more groups selected from the group consisting of phenyl, naphthyl, and biphenyl; a phenyl group which is unsubstituted or substituted by one or more groups selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a deuterated methyl group, a deuterated isopropyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group; a naphthyl group which is unsubstituted or substituted by one or more groups selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a deuterated methyl group, a deuterated isopropyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group; an anthracenyl group which is unsubstituted or substituted by one or more groups selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a deuterated methyl group, a deuterated isopropyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group;a phenanthrenyl group which is unsubstituted or substituted by one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a deuterated methyl group, a deuterated isopropyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group; a triphenylene group which is unsubstituted or substituted by one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a deuterated methyl group, a deuterated isopropyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group; a fluorenyl group which is unsubstituted or substituted by one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a deuterated methyl group, a deuterated isopropyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group; a fluorenyl group which is unsubstituted or substituted by one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a deuterated methyl group, a deuterated isopropyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group; a dibenzofuranyl group which is substituted or unsubstituted by one or more of the group consisting of n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; a dibenzothiophene group which is substituted or unsubstituted by one or more of the group consisting of deuterated atom, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; a carbazolyl group which is substituted or unsubstituted by one or more of the group consisting of deuterated atom, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; a carbazolyl group which is substituted or unsubstituted by one or more of the group consisting of deuterated atom, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated substituted or unsubstituted pyridyl by one or more selected from the group consisting of a deuterated methyl group, a deuterated isopropyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group; substituted or unsubstituted pyrimidyl by one or more selected from the group consisting of a deuterated atom, a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a deuterated methyl group, a deuterated isopropyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group; substituted or unsubstituted pyrazinyl by one or more selected from the group consisting of a deuterated atom, a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a deuterated methyl group, a deuterated isopropyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group; a pyridazinyl group which may be substituted by one or more selected from the group consisting of an alkyl group; a quinolinyl group which may be substituted by one or more selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a deuterated methyl group, a deuterated isopropyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group; an isoquinolinyl group which may be substituted by one or more selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a deuterated methyl group, a deuterated isopropyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group; a quinoxalinyl group which may be substituted by one or more selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a deuterated methyl group, a deuterated isopropyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group;Quinazolinyl substituted or unsubstituted by one or more selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a deuterated methyl group, a deuterated isopropyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group; indanyl substituted or unsubstituted by one or more selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a deuterated methyl group, a deuterated isopropyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group; tetralinyl substituted or unsubstituted by one or more selected from the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a deuterated methyl group, a deuterated isopropyl group, a deuterated tert-butyl group, an adamantyl group, and a norbornyl group; One or more substituted or unsubstituted silyl groups selected from the group consisting of propyl, isopropyl, n-butyl, tert-butyl, phenyl, deuterated phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, halogen-substituted phenyl, cyano-substituted phenyl, adamantyl-substituted phenyl, norbornyl-substituted phenyl, naphthyl, deuterated naphthyl, anthracenyl, phenanthrenyl, biphenyl, pyridyl, pyrimidinyl, dibenzofuranyl, and dibenzothiophenyl, wherein the substituents are one or more. When there are multiple substituents, the multiple substituents may be the same or different. When there are multiple substituents, two adjacent substituents may be linked to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbon ring.

[0055] Preferably, each occurrence of R1 and R5 is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; an isopropyl group; a deuterated isopropyl group; a tert-butyl group; a deuterated tert-butyl group; a cyclopentanyl group; a deuterated cyclopentanyl group; a cyclohexyl group; a deuterated cyclohexanyl group; an adamantyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group; a norbornyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a naphthyl group, a deuterated naphthyl group, an anthracenyl group, a phenanthrenyl group substituted or unsubstituted phenyl by one or more of the group consisting of deuterium atoms, fluorine atoms, cyano groups, methyl groups, deuterated methyl groups, isopropyl groups, deuterated isopropyl groups, tert-butyl groups, deuterated tert-butyl groups, adamantyl groups, norbornyl groups, phenyl groups, deuterated phenyl groups, naphthyl groups, deuterated naphthyl groups; substituted or unsubstituted naphthyl by one or more of the group consisting of deuterium atoms, fluorine atoms, cyano groups, methyl groups, deuterated methyl groups, isopropyl groups, deuterated isopropyl groups, tert-butyl groups, deuterated tert-butyl groups, adamantyl groups, norbornyl groups; substituted or unsubstituted biphenyl by one or more of the group consisting of deuterium atoms, fluorine atoms, cyano groups, methyl groups, deuterated methyl groups, isopropyl groups, deuterated isopropyl groups, tert-butyl groups, deuterated tert-butyl groups, adamantyl groups, norbornyl groups, phenyl groups, naphthyl groups anthracenyl substituted or unsubstituted by one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group, and a naphthyl group; a phenanthrenyl substituted or unsubstituted by one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a fluoren ... a spirobifluorenyl group which is substituted or unsubstituted by one or more of the group consisting of phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; a pyridyl group; a deuterated pyridyl group; a pyrimidinyl group; a deuterated pyrimidinyl group; a triazinyl group which is substituted or unsubstituted by one or more of the group consisting of phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; a quinolyl group which is substituted or unsubstituted by one or more of the group consisting of a deuterium atom, phenyl, and naphthyl; an isoquinolyl group which is substituted or unsubstituted by one or more of the group consisting of a deuterium atom, phenyl, and naphthyl; a dibenzofuranyl group; a deuterated dibenzofuranyl group; a dibenzothiophenyl group; a deuterated dibenzothiophenyl group; a phenylcarbazolyl group; One of them.

[0056] Preferably, at least two adjacent R1 are linked to form a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted norbornyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, One or more substituted or unsubstituted structures selected from the group consisting of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, and a pyrimidine ring.

[0057] Preferably, at least two adjacent R1 are connected to form a deuterium atom, a fluorine atom, a cyano group, a methyl group, an isopropyl group, a tert-butyl group, an adamantyl group, a norbornyl group, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, One of the substituted or unsubstituted structures described below: a benzene ring, a naphthalene ring, a pyridine ring, or a pyrimidine ring.

[0058] Preferably, two adjacent R1s are connected to form one of the following substituted or unsubstituted structures: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring.

[0059] Preferably, two adjacent R1s are connected to form one of the substituted or unsubstituted structures described below: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, or a quinazoline ring, and another two adjacent R1s are connected to form one of the substituted or unsubstituted structures described below: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, or a quinazoline ring.

[0060] Preferably, one of Ar1 and Ar2, i.e., a group represented by formula (IC), is selected from one of the following groups:

[0061]

[0062]

[0063]

[0064]

[0065] Among them, the a 11 Each occurrence is identically or differently selected from 1, 2, 3, 4 or 5; said b 11 Each time you first meet, you can choose from 1, 2, 3 or 4, the same or different; 11 Each occurrence is identically or differently selected from 1, 2 or 3; said d 11 Each occurrence is identically or differently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; said e 11 Each occurrence is identically or differently selected from 1, 2, 3, 4, 5, 6, 7 or 8; said f 11 Each occurrence is the same or different selected from 1 or 2; said g 11 Each occurrence is identically or differently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said h 11 Each time it occurs, it is selected from 0 or 1, either identically or differently;

[0066] The R 11 each occurrence is selected, identically or differently, from a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclopentanyl group, a substituted or unsubstituted cyclohexanyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted norbornyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, One of the following;

[0067] The R 12 Each occurrence is identically or differently selected from one of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, and a substituted or unsubstituted norbornyl group;

[0068] The R 13is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl,

[0069] One of them.

[0070] The other of Ar1 and Ar2 is selected from one of the following groups:

[0071]

[0072]

[0073] Among them, the a 21 Each occurrence is identically or differently selected from 1, 2, 3, 4 or 5; said b 21 Each occurrence is identically or differently selected from 1, 2, 3 or 4; said c 21 Each occurrence is identically or differently selected from 1, 2 or 3; said d 21 Each occurrence is identically or differently selected from 1, 2, 3, 4, 5 or 6; said e 21 Each occurrence is identically or differently selected from 1, 2, 3, 4, 5, 6, 7 or 8; said f 21 Each occurrence is the same or different selected from 1 or 2; said g 21 Each occurrence is identically or differently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said h 21 Each occurrence is identically or differently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; i 21 Each time it occurs, it is selected from 0 or 1, either identically or differently;

[0074] The R 21 Such as R 11 The R 22 Such as R 12 The R 23 Such as R 13 As stated.

[0075] Preferably, each R 11 、R 13 、R 21 、R 23One, two, three, four, five, six or more selected from

[0076]

[0077] Preferably, one of Ar1 and Ar2 is selected from one of the following groups:

[0078]

[0079] Preferably, one of Ar1 and Ar2 is selected from one of the following groups:

[0080]

[0081] The other of Ar1 and Ar2 is selected from one of the following groups:

[0082]

[0083]

[0084] Preferably, the other of Ar1 and Ar2 is selected from one of the following groups:

[0085]

[0086]

[0087] Preferably, the In the above, the Ar 101 is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidylene group, wherein Ar 102 ~Ar 104 is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted pyrimidinyl group, and the Ar 102 ~Ar 104At least one of the following is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, and substituted or unsubstituted pyrimidinyl.

[0088] Preferably, the Ar 101 One selected from a single bond, a phenylene group, a naphthylene group, and a biphenylene group, wherein Ar 102 ~Ar 104 is independently selected from one of methyl, isopropyl, tert-butyl, phenyl, deuterated phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, norbornyl-substituted phenyl, biphenyl, naphthyl-substituted phenyl, pyridyl-substituted phenyl, naphthyl, deuterated naphthyl, anthracenyl, deuterated anthracenyl, phenanthrenyl, deuterated phenanthrenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, N-phenylcarbazolyl, pyridyl, and pyrimidinyl, and Ar 102 ~Ar 104 At least one of the following is selected from phenyl, deuterated phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, norbornyl-substituted phenyl, biphenyl, naphthyl-substituted phenyl, pyridyl-substituted phenyl, naphthyl, deuterated naphthyl, anthracenyl, deuterated anthracenyl, phenanthryl, deuterated phenanthryl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, dibenzofuranyl, dibenzothiophenyl, N-phenylcarbazolyl, pyridyl, and pyrimidinyl.

[0089] Preferably, the Ar 101 Independently selected from a single bond or one of the following groups:

[0090]

[0091]

[0092] More preferably, the Ar 101 Select one of the following structures:

[0093]

[0094] Preferably, the Ar 102 ~Ar 104 At least one (one, two or three) is selected from one of the groups shown below, and the rest are independently selected from one of methyl, isopropyl and tert-butyl:

[0095]

[0096] More preferably, the Ar 102 ~Ar 104 At least one (one, two or three) is selected from one of the groups shown below, and the rest are independently selected from methyl, isopropyl, tert-butyl or one of the groups shown below:

[0097]

[0098] Preferably, in the present invention, the One selected from the following groups:

[0099]

[0100] Preferably, L1 to L5 are independently selected from a single bond or one of the following structures:

[0101]

[0102] Among them, the a 31 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 31 Each occurrence is identically or differently selected from 0, 1, 2 or 3; said c 31 Each occurrence is identically or differently selected from 0, 1 or 2; said d 31 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said e 31 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0103] The R 31 Each occurrence is identically or differently selected from one of the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclopentanyl group, a substituted or unsubstituted cyclohexanyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted norbornyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted silyl group.

[0104] Preferably, L1 to L5 are independently selected from a single bond or one of the following structures:

[0105]

[0106]

[0107] Preferably, the carbazole indole derivatives contain one, two, three, four, five, six

[0108] More preferably, the carbazole indole derivative contains one, two or three

[0109] More preferably, in the carbazole indole derivative, Ar1 contains a and / or Ar2 contains a

[0110]

[0111] Preferably, X1-X 12 At most five of them are selected from N; more preferably, X1-X 12 At most three of them are selected from N; more preferably, X1-X 12 At most two of them are selected from N; Also preferably, X1-X 12 At most one of them is selected from N.

[0112] Preferably, at most two of X1-X4 are selected from N, at most one of X5-X8 is selected from N, and X9-X 12 More preferably, at most one of X1-X4 is selected from N, at most one of X5-X8 is selected from N, and X9-X 12 At most one of them is selected from N.

[0113] Preferably, the carbazole indole derivative has one of the structures shown in formula (II-A) to (II-E):

[0114]

[0115] Among them, the X1 to X 12 , Ar1, Ar2, L2, and L3 are all as described in the present invention.

[0116] Preferably, in formula (II-A) and formula (II-B), at least two adjacent R1s in X1 to X4 are connected to form one of the following substituted or unsubstituted structures: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, or a quinazoline ring; and / or adjacent R1s in X5 to X6 are connected to form one of the following substituted or unsubstituted structures: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, or a quinazoline ring; and / or X9 to X 12 At least two adjacent R1s are connected to form one of the following substituted or unsubstituted structures: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, and quinazoline ring.

[0117] Also preferably, in formula (II-A) and formula (II-B), adjacent R1s in X1 to X2 are connected to form one of the substituted or unsubstituted structures described below: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, or a quinazoline ring; and / or adjacent R1s in X3 to X4 are connected to form one of the substituted or unsubstituted structures described below: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, or a quinazoline ring; and / or adjacent R1s in X5 to X6 are connected to form one of the substituted or unsubstituted structures described below: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, or a quinazoline ring; and / or X9 to X 10 wherein adjacent R1 are connected to form one of the following substituted or unsubstituted structures: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring; and / or X 11 ~X 12 Adjacent R1 are connected to form one of the following substituted or unsubstituted structures: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring.

[0118] Preferably, in formula (II-C) and formula (II-D), at least two adjacent R1s among X1 to X4 are connected to form one of the following substituted or unsubstituted structures: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring; and / or X9 to X 12 At least two adjacent R1s are connected to form one of the following substituted or unsubstituted structures: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, and quinazoline ring.

[0119] Also preferably, in formula (II-C) and formula (II-D), adjacent R1 in X1 to X2 are connected to form one of the following substituted or unsubstituted structures: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, or a quinazoline ring; and / or adjacent R1 in X3 to X4 are connected to form one of the following substituted or unsubstituted structures: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, or a quinazoline ring; and / or X9 to X 10 wherein adjacent R1 are connected to form one of the following substituted or unsubstituted structures: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring; and / or X 11 ~X 12 Adjacent R1 are connected to form one of the following substituted or unsubstituted structures: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring.

[0120] Preferably, in formula (II-E), at least two adjacent R1s in X1 to X4 are connected to form one of the following substituted or unsubstituted structures: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, or a quinazoline ring; and / or adjacent R1s in X7 to X8 are connected to form one of the following substituted or unsubstituted structures: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, or a quinazoline ring; and / or X9 to X 12 At least two adjacent R1s are connected to form one of the following substituted or unsubstituted structures: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, and quinazoline ring.

[0121] Also preferably, in formula (II-E), adjacent R1s in X1 to X2 are connected to form one of the substituted or unsubstituted structures described below: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, or a quinazoline ring; and / or adjacent R1s in X3 to X4 are connected to form one of the substituted or unsubstituted structures described below: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, or a quinazoline ring; and / or adjacent R1s in X7 to X8 are connected to form one of the substituted or unsubstituted structures described below: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, or a quinazoline ring; and / or X9 to X 10wherein adjacent R1 are connected to form one of the following substituted or unsubstituted structures: a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring; and / or X 11 ~X 12 Adjacent R1 are connected to form one of the following substituted or unsubstituted structures: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring.

[0122] Preferably, the carbazole indole derivative has one of the structures shown in formula (III-1) to (III-32):

[0123]

[0124]

[0125] Among them, the a 41 Each occurrence is identically or differently selected from 1, 2, 3, 4, 5 or 6; said b 41 Each time it occurs, the same or different is selected from 1 or 2; said c 41 Each occurrence is identically or differently selected from 1, 2, 3 or 4; said d 41 Each occurrence is identically or differently selected from 1, 2, 3, 4, 5, 6, 7 or 8;

[0126] The R 41 R in the present invention 11 same;

[0127] Said Ar1, Ar2, L2, and L3 are as described in the present invention;

[0128] Provided that the molecule contains at least one of the following groups: wherein said Z is selected from carbon atom or silicon atom, said Ar 101 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C4-C30 heteroarylene group, wherein Ar 102 ~Ar 104 is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C2-C30 heteroaryl group, and the Ar 102 ~Ar104 At least one of the following is selected from a substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a substituted or unsubstituted C2-C30 heteroaryl group.

[0129] Preferably, each R 11 、R 21 、R 41 At least one selected from

[0130] More preferably, each R 11 、R 21 、R 41 One or two selected from

[0131] More preferably, each R 11 One of the and / or each R 21 One of the

[0132] Preferably, the carbazole indole derivative has one of the structures shown in formula (IV-A) to (IV-V):

[0133]

[0134]

[0135] Among them, the a 41 、b 41 、c 41 、R 41 , Ar1, Ar2, L2, L3 are as described in the present invention;

[0136] Each occurrence of Y is identically or differently selected from one of an oxygen atom, a sulfur atom, N-L4-R2, and CR3R4; Y1 to Y8 are independently selected from a nitrogen atom or C-L5-R5; and R2, R3, R4, R5, L4, and L5 are as described herein;

[0137] Provided that the molecule contains at least one of the following groups: wherein said Z is selected from carbon atom or silicon atom, said Ar 101 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C4-C30 heteroarylene group, wherein Ar 102 ~Ar 104is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C2-C30 heteroaryl group, and the Ar 102 ~Ar 104 At least one of the following is selected from a substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a substituted or unsubstituted C2-C30 heteroaryl group.

[0138] Preferably, That is, the group represented by formula (IC) is as described in the present invention.

[0139] Preferably, each R 11 、R 21 、R 41 At least one selected from

[0140] More preferably, each R 11 、R 21 、R 41 One or two selected from

[0141] More preferably, each R 11 One of the and / or each R 21 One of the

[0142] Preferably, the carbazole indole derivative has one of the structures shown in formula (V-1) to (V-48):

[0143]

[0144]

[0145] Among them, the a 41 、b 41 、c 41 、R 41 , Ar1, Ar2, L2, L3, Y, Y1~Y8, Z, Ar 101 ~Ar 104 All as described in the present invention. Preferably, That is, the group represented by formula (IC) is as described in the present invention.

[0146] Preferably, the carbazole indole derivative has one of the structures shown in formula (VI-1) to (VI-38):

[0147]

[0148]

[0149] Among them, the a 41 、b 41 、c 41 、R 41 , Ar1, Ar2, L2, L3 are as described in the present invention;

[0150] Provided that the molecule contains at least one of the following groups: Wherein said Z is selected from carbon atom or silicon atom

[0151] Sub, the Ar 101 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C4-C30 heteroarylene group, wherein Ar 102 ~Ar 104 is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C2-C30 heteroaryl group, and the Ar 102 ~Ar 104 At least one of the following is selected from a substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a substituted or unsubstituted C2-C30 heteroaryl group.

[0152] Preferably, each R 11 、R 21 、R 41 At least one selected from

[0153] More preferably, each R 11 、R 21 、R 41 One or two selected from

[0154] More preferably, each R 11 One of the and / or each R21 One of the Preferably, the carbazole indole derivative has one of the structures shown in formula (VII-1) to (VII-44):

[0155]

[0156]

[0157] Among them, the a 41 、b 41 、c 41 、R 41 , Ar1, Ar2, L2, L3 are as described in the present invention;

[0158] Each occurrence of Y is identically or differently selected from one of an oxygen atom, a sulfur atom, N-L4-R2, and CR3R4; Y1 to Y8 are independently selected from a nitrogen atom or C-L5-R5; and R2, R3, R4, R5, L4, and L5 are as described herein;

[0159] Provided that the molecule contains at least one of the following groups: wherein said Z is selected from carbon atom or silicon atom, said Ar 101 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C4-C30 heteroarylene group, wherein Ar 102 ~Ar 104 is independently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C2-C30 heteroaryl group, and the Ar 102 ~Ar 104 At least one of the following is selected from a substituted or unsubstituted C6-C30 aryl group, a monovalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, and a substituted or unsubstituted C2-C30 heteroaryl group.

[0160] Preferably, That is, the group represented by formula (IC) is as described in the present invention.

[0161] Preferably, each R 11 、R 21 、R 41At least one selected from

[0162] More preferably, each R 11 、R 21 、R 41 One or two selected from

[0163] More preferably, each R 11 One of the and / or each R 21 One of the

[0164] Preferably, the carbazole indole derivative has one of the structures shown in formula (VIII-1) to (VIII-66):

[0165]

[0166]

[0167]

[0168] Among them, the a 41 、b 41 、c 41 、R 41 , Ar1, L2, L3, Y, Y1~Y8, Z, Ar 201 ~Ar 204 Most preferably, the carbazole indole derivative is selected from one of the following compounds:

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204] The above lists only some of the specific structural forms of the carbazole indole derivatives described in the present invention, but the present invention is not limited to these chemical structures listed. All chemical structures based on formulas (IA), (IB) and (IC) and substituents as defined in the present invention are included.

[0205] The carbazoloindole derivatives of the present invention can be prepared by the following synthetic route:

[0206]

[0207] Wherein, Z1 and Z2 are independently selected from chlorine atom, bromine atom or iodine atom;

[0208] The X1~X 12 , L2, L3, Ar1, and Ar2 are all as described in the present invention.

[0209] In the above synthetic route, compound (M) reacts with halides (N1) and (N2) through a CN coupling reaction to obtain the carbazoloindole derivative of the present invention. The order of reaction between compound (M) and halides (N1) and (N2) is not limited; i.e., compound (M) can react with (N1) first and then with (N2), or with (N2) first and then with (N1).

[0210] The above reaction route adopts the reaction type commonly used in organic synthesis, and the reaction conditions (for example, the selection of the types of reaction solvent, catalyst, ligand, base, etc., the amount used, and the order and method of addition) are not particularly limited. The above preparation method has readily available raw materials, a simple preparation process, and excellent yield. The present invention can also be synthesized using the conventional reaction type in other organic synthesis without particular limitation, and the above is only an example of a synthetic route.

[0211] The present invention also provides an organic electroluminescent device comprising an anode, a cathode and an organic layer, wherein the organic layer comprises a hole transport region between the anode and the cathode, a light-emitting layer, an electron transport region and at least one of a covering layer on the side of the cathode facing away from the anode, and the organic layer contains one or more of the carbazole and indole derivatives described in the present invention.

[0212] Preferably, the organic layer includes a light-emitting layer, and the light-emitting layer contains one or more carbazole indole derivatives described in the present invention.

[0213] Preferably, the light-emitting layer includes a guest material and a host material, and the host material contains one or more of the carbazole indole derivatives described in the present invention.

[0214] Preferably, the light-emitting layer contains two or more host materials, and the host materials contain one or more of the carbazole indole derivatives described in the present invention.

[0215] The hole transport region of the present invention includes at least one layer of a hole injection layer, a hole transport layer and a light-emitting auxiliary layer.

[0216] The hole injection layer of 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, radialene compounds, and other substances with high hole injection properties can be used, for example, 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'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT / PSS), compounds HT-1 to HT-19, and compounds p-1 to p-3, but are not limited thereto.

[0217]

[0218] The hole transport layer of the present invention can be a single layer structure composed of a single substance, or a single layer structure or a multilayer structure composed of different substances. Triarylamine compounds can be used, or other materials with hole mobility in the range of 10 -6 cm 2 / Vs or above, for example, N,N'-diphenyl-N,N'-di(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 compounds HT-1 to HT-19 shown above, but not limited thereto.

[0219] The light-emitting auxiliary layer of 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, and other substances with appropriate HOMO and T1 energy levels can also 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-furan-2-yl)-9,9'-spirobifluorene-2-amine, N,N-di([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, and compounds HT-1 to HT-19 shown above, but are not limited thereto.

[0220] The light-emitting layer of the present invention includes a guest material and a host material, and a dual host material formed by two host materials can be used. The guest material can use a fluorescent compound, such as a pyrene derivative, a fluoranthene derivative, an aromatic amine derivative, etc. Examples include 10-(2-benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolinazine-11-one (C545T), 4,4'-bis(9-ethyl-3-carbazole vinyl)-1,1'-biphenyl (BCzVBi), 4, 4'-bis[4-(di-p-tolylamino)phenylvinyl]biphenyl (DPAVBi), etc. Phosphorescent materials can also be used, such as metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Examples include bis(4,6-difluorophenylpyridine-N,C2)picolinoyliridium (FIrpic), tris(2-phenylpyridine)iridium (Ir(ppy)3), di(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), etc. The host material preferably uses a substance having a higher LUMO and a lower HOMO than that of the guest material, such as a metal complex such as an aluminum complex or a zinc complex, a heterocyclic compound such as an oxadiazole derivative, a benzoxazole derivative, a benzothiazole derivative or a benzimidazole derivative, a fused aromatic compound such as a carbazole derivative or anthracene derivative, an aromatic amine compound such as a triarylamine derivative or a fused polycyclic aromatic amine derivative, examples of which include Alq3, BAlq, TPBI, TPD, 4,4'-di(9-carbazole)biphenyl (CBP), 4,4',4"-tri(carbazole-9-yl)triphenylamine (TCTA), 9,10-di(2-naphthyl)anthracene (ADN), and the carbazole and indole derivatives described in the present invention, but are not limited thereto.

[0221] The electron transport region of the present invention includes at least one layer of an electron injection layer, an electron transport layer and a hole blocking layer.

[0222] The electron injection layer of 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. One or more of the following substances may be selected: alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances with high electron injection properties. Examples include, but are not limited to, Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, and the like.

[0223] 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, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, polymer compounds, etc. with high electron transport properties can be used. Examples include 8-hydroxyquinoline aluminum (Alq3), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), and 2-(4-biphenyl)-5-phenyloxadiazole (PBD), but are not limited thereto.

[0224] The hole blocking layer of the present invention can be a single layer structure composed of a single material, or a single layer structure or a multilayer structure composed of different materials. The selected material requires a T1 energy level higher than 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 must be lower than the HOMO energy level of the main material of the light-emitting layer, so as to play a role in blocking holes. Furthermore, the electron mobility of the hole blocking layer material used is 10 -6 cm 2 / Vs or above, which facilitates electron transport. 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, polymer compounds, etc. Examples include, but are not limited to, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBI) and BAlq.

[0225] The anode described in the present invention can be a reflective anode, such as a reflective film formed by silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb) or their alloys, or a layer structure with a high work function and being transparent or translucent, such as a layer structure formed by indium tin oxide (ITO), indium zinc oxide (ZnO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In2O3) or tin oxide (SnO2). The specific type of anode depends on the type of device to be prepared. If the device to be prepared is a bottom-emitting device (emitting light on the anode side), a transparent or translucent anode needs to be made. If the device to be prepared is a top-emitting device (emitting light on the cathode side), a reflective anode needs to be made.

[0226] The cathode described in the present invention can be a thin film with a low work function made of lithium, calcium, lithium fluoride / calcium, lithium fluoride / aluminum, aluminum, silver, magnesium, magnesium-silver alloy, etc., and can be made into a reflective electrode, a transparent electrode or a semi-transparent electrode by adjusting the thickness of the film. If a bottom-emitting device is to be prepared, a reflective cathode needs to be made. If a top-emitting device is to be prepared, a transparent or semi-transparent cathode needs to be made.

[0227] The cover layer of 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. The cover layer material may be an organic or inorganic substance with an appropriate refractive index, such as a metal halide, oxide, nitride, nitrogen oxide, sulfide, selenide, aromatic hydrocarbon compound, heteroaromatic hydrocarbon compound, aromatic amine compound, etc. Examples include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, ZnS, Alq3, compound CP-1, compound CP-2, compound CP-3, compound CP-4, and the aromatic amine compound of the present invention, but are not limited thereto.

[0228]

[0229] Preferably, the organic layer comprises a hole transport region, a light-emitting layer and an electron transport region, and the light-emitting layer contains one or more of the carbazole indole derivatives described in the present invention.

[0230] Preferably, the organic layer includes a hole transport region, a light-emitting layer, an electron transport region and a covering layer, and the light-emitting layer contains one or more of the carbazole and indole derivatives described in the present invention.

[0231] 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, and the light-emitting layer contains one or more of the carbazole indole derivatives described in the present invention.

[0232] 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, and the light-emitting layer contains one or more of the carbazole indole derivatives described in the present invention.

[0233] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a luminescent layer, an electron transport layer and an electron injection layer, and the luminescent layer contains one or more of the carbazole indole derivatives described in the present invention.

[0234] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a luminescent layer, a hole blocking layer, an electron transport layer and an electron injection layer, and the luminescent layer contains one or more of the carbazole indole derivatives described in the present invention.

[0235] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a covering layer, and the light-emitting layer contains one or more of the carbazole indole derivatives described in the present invention.

[0236] 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, an electron injection layer and a covering layer, and the light-emitting layer contains one or more of the carbazole and indole derivatives described in the present invention.

[0237] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a luminescent layer, an electron transport layer, an electron injection layer and a covering layer, and the luminescent layer contains one or more of the carbazole indole derivatives described in the present invention.

[0238] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a luminescent layer, a hole blocking layer, an electron transport layer, an electron injection layer and a covering layer, and the luminescence auxiliary layer contains one or more of the aromatic amine compounds described in the present invention.

[0239] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a luminescent layer, a hole blocking layer, an electron transport layer, an electron injection layer and a covering layer, and the luminescent layer contains one or more of the carbazole indole derivatives described in the present invention.

[0240] The organic layers, cathode, anode, and cover layer can be formed using any of the following methods: vacuum deposition, inkjet printing, sputtering, plasma deposition, ion plating, spin coating, dipping, or screen printing. The thickness of each layer is not particularly limited, provided that good device performance is achieved. Preferably, the organic layers are formed using vacuum deposition, inkjet printing, or spin coating.

[0241] The thickness of each organic layer and the 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.

[0242] The organic electroluminescent device provided by the present invention can be applied to fields such as lighting and display, and can be specifically listed as smartphone display screens, tablet computer display screens, smart wearable device display screens, large-size displays such as televisions, VR and car taillights.

[0243] The technical solutions and technical effects of the present invention are further described below with reference to embodiments and comparative examples.

[0244] The mass spectra of the compounds of the present invention were determined using a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters, UK, using chloroform as the solvent.

[0245] The elemental analysis was performed using a Vario EL cube organic element analyzer from Elementar, Germany, with a sample mass of 5 to 10 mg.

[0246] Synthesis Example 1: Synthesis of Compound N

[0247]

[0248] Synthesis of compound N-180:

[0249] Under nitrogen, A-180 (20.00 mmol, 8.31 g), B-180 (20.00 mmol, 3.13 g), potassium carbonate (30.00 mmol, 4.15 g), and Pd2(dba)3 (0.20 mmol, 0.18 g) were added to a reaction flask. 180 ml of a 2:1:1 toluene / ethanol / water mixture was added and stirred. The reaction system was heated under reflux for 6 h. After the reaction was completed, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. The mixture was cooled and crystallized, filtered, and the resulting solid was recrystallized from toluene to obtain compound N-180 (6.97 g, 78%). The purity of the solid was ≥99.71% as determined by HPLC. Mass spectrum: m / z: 446.1267 (theoretical value: 446.1258).

[0250] According to the above synthesis method, other compounds N required by the present invention were synthesized. The relevant raw materials are shown in Table 101:

[0251] Table 101:

[0252]

[0253] Synthesis Example 2: Synthesis of Compound 27

[0254]

[0255] Compound M-27 (10.00 mmol, 4.77 g), N-27 (12.00 mmol, 4.79 g), palladium acetate (1.10 mmol, 0.25 g), 2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl (2.00 mmol, 0.82 g), sodium tert-butoxide (15.00 mmol, 1.44 g) and 50 ml of o-xylene were added to the reaction vessel, and the mixture was stirred under reflux for 4.5 h. After the reaction was completed, the mixture was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was then dried over magnesium sulfate and the solvent was removed by rotary evaporation. Compound 27 (4.85 g, 61%) was obtained by recrystallization from o-xylene. The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 794.3225 (theoretical value: 794.3235). Theoretical element content (%) C 59 H 34 D4N2O: C, 89.14; H, 5.32; N, 3.52. Measured element content (%): C, 89.13; H, 5.33; N, 3.51.

[0256] Synthesis Example 3: Synthesis of Compound 47

[0257]

[0258] According to the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-47 to obtain compound 47 (5.59 g, 63%). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 886.3333 (theoretical value: 886.3320). Theoretical element content (%) C 65 H 38 D4N2S: C, 88.00; H, 5.23; N, 3.16. Measured element content (%): C, 88.01; H, 5.25; N, 3.15.

[0259] Synthesis Example 4: Synthesis of Compound 83

[0260]

[0261] According to the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-83 to obtain compound 83 (5.13 g, 59%). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 869.3718 (theoretical value: 869.3708). Theoretical element content (%) C 65 H 39D4N3: C, 89.73; H, 5.44; N, 4.83. Measured element content (%): C, 89.75; H, 5.45; N, 4.81.

[0262] Synthesis Example 5: Synthesis of Compound 120

[0263]

[0264] According to the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-120 to obtain compound 120 (5.64 g, 65%). The solid purity was ≥99.98% as determined by HPLC. Mass spectrum m / z: 866.3675 (theoretical value: 866.3661). Theoretical element content (%) C 66 H 46 N2: C, 91.42; H, 5.35; N, 3.23. Measured element content (%): C, 91.41; H, 5.38; N, 3.22.

[0265] Synthesis Example 6: Synthesis of Compound 172

[0266]

[0267] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-172, and N-27 was replaced with an equal molar amount of A-180 to obtain Compound 172 (5.65 g, 64%). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 882.3055 (theoretical value: 882.3066). Theoretical element content (%): C 64 H 42 N2OSi: C, 87.04; H, 4.79; N, 3.17. Measured element content (%): C, 87.06; H, 4.78; N, 3.18.

[0268] Synthesis Example 7: Synthesis of Compound 180

[0269]

[0270] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-180, and N-27 was replaced with an equal molar amount of N-180 to obtain Compound 180 (5.83 g, 66%). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 882.3058 (theoretical value: 882.3066). Theoretical element content (%): C 64 H 42 N2OSi: C, 87.04; H, 4.79; N, 3.17. Measured element content (%): C, 87.05; H, 4.77; N, 3.16.

[0271] Synthesis Example 8: Synthesis of Compound 241

[0272]

[0273] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-241, and N-27 was replaced with an equal molar amount of A-692 to obtain Compound 241 (5.47 g, 62%). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 881.3218 (theoretical value: 881.3226). Theoretical element content (%): C 64 H 43 N3Si: C, 87.14; H, 4.91; N, 4.76. Measured element content (%): C, 87.15; H, 4.92; N, 4.75.

[0274] Synthesis Example 9: Synthesis of Compound 361

[0275]

[0276] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-361, and N-27 was replaced with an equal molar amount of N-361 to obtain Compound 361 (4.69 g, 58%). The solid purity was ≥99.98% as determined by HPLC. Mass spectrum m / z: 807.2718 (theoretical value: 807.2706). Theoretical element content (%): C 57 H 37 N3OSi: C, 84.73; H, 4.62; N, 5.20. Measured element content (%): C, 84.72; H, 4.63; N, 5.21.

[0277] Synthesis Example 10: Synthesis of Compound 384

[0278]

[0279] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-384, and N-27 was replaced with an equal molar amount of N-384 to obtain compound 384 (5.40 g, 60%). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 898.2823 (theoretical value: 898.2838). Theoretical element content (%): C 64 H 42 N2SSi: C, 85.49; H, 4.71; N, 3.12. Measured element content (%): C, 85.47; H, 4.69; N, 3.13.

[0280] Synthesis Example 11: Synthesis of Compound 459

[0281]

[0282] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-459, and N-27 was replaced with an equal molar amount of A-180 to obtain Compound 459 (5.39 g, 61%). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 882.3075 (theoretical value: 882.3066). Theoretical element content (%): C 64 H 42 N2OSi: C, 87.04; H, 4.79; N, 3.17. Measured element content (%): C, 87.05; H, 4.76; N, 3.16.

[0283] Synthesis Example 12: Synthesis of Compound 467

[0284]

[0285] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-467, and N-27 was replaced with an equal molar amount of A-692 to obtain Compound 467 (5.54 g, 68%). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 813.3185 (theoretical value: 813.3193). Theoretical element content (%): C 58 H 31 D7N2OSi: C, 85.57; H, 5.57; N, 3.44. Measured element content (%): C, 85.54; H, 5.56; N, 3.46.

[0286] Synthesis Example 13: Synthesis of Compound 509

[0287]

[0288] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-509, and N-27 was replaced with an equal molar amount of N-361 to obtain Compound 509 (4.76 g, 59%). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 806.2742 (theoretical value: 806.2753). Theoretical element content (%): C 58 H 38 N2OSi: C, 86.32; H, 4.75; N, 3.47. Measured element content (%): C, 86.38; H, 4.72; N, 3.48.

[0289] Synthesis Example 14: Synthesis of Compound 511

[0290]

[0291] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-511, and N-27 was replaced with an equal molar amount of N-361 to obtain Compound 511 (5.23 g, 61%). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 856.2918 (theoretical value: 856.2910). Theoretical element content (%): C 62 H 40 N2OSi: C, 86.88; H, 4.70; N, 3.27. Measured element content (%): C, 86.85; H, 4.71; N, 3.28.

[0292] Synthesis Example 15: Synthesis of Compound 541

[0293]

[0294] According to the preparation method of Synthesis Example 2, N-27 was replaced with an equal molar amount of N-541 to obtain compound 541 (6.00 g, 64%). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 936.3485 (theoretical value: 936.3474). Theoretical element content (%) C 68 H 40 D4N2OSi: C, 87.15; H, 5.16; N, 2.99. Measured element content (%): C, 87.16; H, 5.18; N, 2.98.

[0295] Synthesis Example 16: Synthesis of Compound 567

[0296]

[0297] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-467, and N-27 was replaced with an equal molar amount of N-567 to obtain Compound 567 (6.05 g, 65%). The solid purity was ≥99.98% as determined by HPLC. Mass spectrum m / z: 929.3833 (theoretical value: 929.3819). Theoretical element content (%): C 67 H 39 D7N2OSi: C, 86.51; H, 5.74; N, 3.01. Measured element content (%): C, 86.53; H, 5.71; N, 3.00.

[0298] Synthesis Example 17: Synthesis of Compound 634

[0299]

[0300] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-634, and N-27 was replaced with an equal molar amount of N-384 to obtain compound 634 (5.26 g, 63%). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 834.3288 (theoretical value: 834.3278). Theoretical element content (%): C 58 H 26 D 12 N2SSi: C, 83.41; H, 6.03; N, 3.35. Measured element content (%): C, 83.43; H, 6.05; N, 3.33.

[0301] Synthesis Example 18: Synthesis of Compound 665

[0302]

[0303] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-47, and N-27 was replaced with an equal molar amount of A-180 to obtain compound 665 (6.05 g, 67%). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 902.3075 (theoretical value: 902.3089). Theoretical element content (%): C 64 H 38 D4N2SSi: C, 85.11; H, 5.13; N, 3.10. Measured element content (%): C, 85.10; H, 5.12; N, 3.11.

[0304] Synthesis Example 19: Synthesis of Compound 678

[0305]

[0306] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-678, and N-27 was replaced with an equal molar amount of N-384 to obtain Compound 678 (5.02 g, 61%). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 822.2538 (theoretical value: 822.2525). Theoretical element content (%): C 58 H 38 N2SSi: C, 84.64; H, 4.65; N, 3.40. Measured element content (%): C, 84.66; H, 4.66; N, 3.38.

[0307] Synthesis Example 20: Synthesis of Compound 692

[0308]

[0309] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-692, and N-27 was replaced with an equal molar amount of N-692 to obtain Compound 692 (5.82 g, 64%). The solid purity was ≥99.98% as determined by HPLC. Mass spectrum m / z: 908.3577 (theoretical value: 908.3587). Theoretical element content (%): C 67 H 48 N2Si: C, 88.51; H, 5.32; N, 3.08. Measured element content (%): C, 88.53; H, 5.31; N, 3.10.

[0310] Synthesis Example 21: Synthesis of Compound 798

[0311]

[0312] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-509, and N-27 was replaced with an equal molar amount of N-798 to obtain Compound 798 (5.73 g, 60%). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 954.3443 (theoretical value: 954.3430). Theoretical element content (%): C 71 H 46 N2Si: C, 89.27; H, 4.85; N, 2.93. Measured element content (%): C, 89.28; H, 4.83; N, 2.95.

[0313] Synthesis Example 22: Synthesis of Compound 849

[0314]

[0315] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-849, and N-27 was replaced with an equal molar amount of A-180 to obtain Compound 849 (5.94 g, 67%). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 885.3488 (theoretical value: 885.3477). Theoretical element content (%): C 64 H 39 D4N3Si: C, 86.74; H, 5.35; N, 4.74. Measured element content (%): C, 86.72; H, 5.33; N, 4.75.

[0316] Synthesis Example 23: Synthesis of Compound 876

[0317]

[0318] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-876, and N-27 was replaced with an equal molar amount of N-876 to obtain Compound 876 (5.47 g, 61%). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 896.2868 (theoretical value: 896.2859). Theoretical element content (%): C 64 H 40 N2O2Si: C, 85.69; H, 4.49; N, 3.12. Measured element content (%): C, 85.71; H, 4.50; N, 3.11.

[0319] Synthesis Example 24: Synthesis of Compound 908

[0320]

[0321] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-908, and N-27 was replaced with an equal molar amount of A-692 to obtain Compound 908 (5.40 g, 63%). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 856.2923 (theoretical value: 856.2910). Theoretical element content (%): C 62 H 40 N2OSi: C, 86.88; H, 4.70; N, 3.27. Measured element content (%): C, 86.85; H, 4.72; N, 3.30.

[0322] Synthesis Example 25: Synthesis of Compound 931

[0323]

[0324] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-931, and N-27 was replaced with an equal molar amount of N-931 to obtain Compound 931 (5.76 g, 66%). The solid purity was ≥99.98% as determined by HPLC. Mass spectrum m / z: 872.2695 (theoretical value: 872.2681). Theoretical element content (%): C 62 H 40 N2SSi: C, 85.29; H, 4.62; N, 3.21. Measured element content (%): C, 85.28; H, 4.59; N, 3.23.

[0325] Synthesis Example 26: Synthesis of Compound 942

[0326]

[0327] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-942, and N-27 was replaced with an equal molar amount of A-180 to obtain Compound 942 (5.59 g, 64%). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 872.2690 (theoretical value: 872.2681). Theoretical element content (%): C 62 H 40 N2SSi: C, 85.29; H, 4.62; N, 3.21. Measured element content (%): C, 85.27; H, 4.63; N, 3.24.

[0328] Synthesis Example 27: Synthesis of Compound 971

[0329]

[0330] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-971, and N-27 was replaced with an equal molar amount of A-180 to obtain Compound 971 (5.48 g, 62%). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 882.3442 (theoretical value: 882.3430). Theoretical element content (%): C 65 H 46 N2Si: C, 88.40; H, 5.25; N, 3.17. Measured element content (%): C, 88.42; H, 5.28; N, 3.14.

[0331] Synthesis Example 28: Synthesis of Compound 975

[0332]

[0333] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-975, and N-27 was replaced with an equal molar amount of N-975 to obtain Compound 975 (5.78 g, 65%). The solid purity was ≥99.98% as determined by HPLC. Mass spectrum m / z: 888.3908 (theoretical value: 888.3900). Theoretical element content (%): C 65 H 52 N2Si: C, 87.80; H, 5.89; N, 3.15. Measured element content (%): C, 87.85; H, 5.88; N, 3.14.

[0334] Synthesis Example 29: Synthesis of Compound 984

[0335]

[0336] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-984, and N-27 was replaced with an equal molar amount of A-692 to obtain Compound 984 (5.64 g, 61%). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 924.3891 (theoretical value: 924.3900). Theoretical element content (%): C 68 H 52 N2Si: C, 88.27; H, 5.66; N, 3.03. Measured element content (%): C, 88.28; H, 5.67; N, 3.02.

[0337] Synthesis Example 30: Synthesis of Compound 1044

[0338]

[0339] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-1044, and N-27 was replaced with an equal molar amount of N-1044 to obtain Compound 1044 (5.39 g, 59%). HPLC analysis of the solid purity was ≥99.96%. Mass spectrum m / z: 912.2638 (theoretical value: 912.2631). Theoretical element content (%): C 64 H 40 N2OSSi: C, 84.18; H, 4.42; N, 3.07. Measured element content (%): C, 84.16; H, 4.44; N, 3.08.

[0340] Synthesis Example 31: Synthesis of Compound 1057

[0341]

[0342] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-1044, and N-27 was replaced with an equal molar amount of N-1057 to obtain Compound 1057 (5.25 g, 65%). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 807.2718 (theoretical value: 807.2706). Theoretical element content (%): C 57 H 37 N3OSi: C, 84.73; H, 4.62; N, 5.20. Measured element content (%): C, 84.72; H, 4.61; N, 5.21.

[0343] Synthesis Example 32: Synthesis of Compound 1085

[0344]

[0345] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-1085, and N-27 was replaced with an equal molar amount of N-1085 to obtain Compound 1085 (5.60 g, 60%). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 932.3595 (theoretical value: 932.3587). Theoretical element content (%): C 69 H 48 N2Si: C, 88.80; H, 5.18; N, 3.00. Measured element content (%): C, 88.85; H, 5.16; N, 2.99.

[0346] Synthesis Example 33: Synthesis of Compound 1159

[0347]

[0348] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-931, and N-27 was replaced with an equal molar amount of N-361 to obtain compound 1159 (5.84 g, 64%). The solid purity was ≥99.98% as determined by HPLC. Mass spectrum m / z: 912.2623 (theoretical value: 912.2631). Theoretical element content (%): C 64 H 40 N2OSSi: C, 84.18; H, 4.42; N, 3.07. Measured element content (%): C, 84.17; H, 4.43; N, 3.08.

[0349] Synthesis Example 34: Synthesis of Compound 1166

[0350]

[0351] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-47, and N-27 was replaced with an equal molar amount of N-1166 to obtain compound 1166 (5.53 g, 71%). The solid purity was ≥99.93% as determined by HPLC. Mass spectrum m / z: 778.2763 (theoretical value: 78.2776). Theoretical element content (%): C 54 H 34 D4N2SSi: C, 83.25; H, 5.43; N, 3.60. Measured element content (%): C, 83.22; H, 5.41; N, 3.64.

[0352] Synthesis Example 35: Synthesis of Compound 1172

[0353]

[0354] Following the preparation method of Synthesis Example 2, M-27 was replaced with an equal molar amount of M-459, and N-27 was replaced with an equal molar amount of N-1172 to obtain Compound 1172 (5.75 g, 70%). HPLC analysis of the solid showed a purity of ≥99.94%. Mass spectrum m / z: 820.2930 (theoretical value: 820.2910). Theoretical element content (%): C 59 H 40 N2OSi: C, 86.31; H, 4.91; N, 3.41. Measured element content (%): C, 86.28; H, 4.94; N, 3.42.

[0355] The organic materials used in the device preparation examples were purified by sublimation, with a purity of more than 99.99%. The ITO glass substrate and ITO / Ag / ITO glass substrate used in the device preparation examples were purchased from the market.

[0356] The following are other compounds used in the device preparation examples in addition to the carbazole indole derivatives described in the present invention:

[0357]

[0358] The test software, computer, K2400 digital source meter from Keithley Company, USA and PR788 spectrum scanning luminance meter from Photo Research Company, USA were used to form a combined IVL test system. The device prepared by the present invention was tested at a current density of 15 mA / cm at atmospheric pressure and room temperature. 2 The luminous efficiency and driving voltage at the time of 100 s are shown in Tables 1 and 2. The lifespan of the device prepared in the present invention was tested using the McScience M6000 OLED lifespan test system at atmospheric pressure and room temperature (brightness decays to 95% of the initial brightness).

[0359] Comparative device preparation example 1: Comparative device 1

[0360] First, the ITO / Ag / ITO glass substrate was ultrasonically cleaned twice with deionized water for 20 minutes each time, and then ultrasonically cleaned with isopropyl alcohol, acetone and methanol for 20 minutes each, followed by exposure to ultraviolet light and ozone for 30 minutes, and finally placed in a vacuum evaporation equipment for use.

[0361] The following layers were evaporated layer by layer on the above-mentioned ITO / Ag / ITO glass substrate: a, HT-8 and p-1 (mass ratio of 100:3) as hole injection layer with a thickness of 20 nm; b, HT-8 as hole transport layer with a thickness of 30 nm; c, HOST-1, RH and Ir(dpm)(piq)2 (mass ratio of 48:48:4) as light-emitting layer with a thickness of 35 nm; d, BAlq as hole blocking layer with a thickness of 25 nm; e, NBphen and Liq (mass ratio of 7:3) as electron transport layer with a thickness of 20 nm; f, LiF as electron injection layer with a thickness of 0.1 nm; g, Mg and Ag (mass ratio of 1:7) as cathode with a thickness of 10 nm; h: CP-4 as covering layer with a thickness of 100 nm.

[0362] Comparative device preparation examples 2 to 3: Comparative devices 2 to 3

[0363] HOST-1 is replaced by HOST-2, and the other steps are the same as those in Comparative Device Preparation Example 1 to obtain Comparative Device Preparation Example 2.

[0364] Device Preparation Examples 1-34: Light-Emitting Devices 1-34

[0365] Light-emitting devices 1 to 34 are obtained by replacing HOST-1 with the carbazole indole derivatives of the present invention prepared in Synthesis Examples 2 to 35, and following the same other steps as in Comparative Device Preparation Example 1.

[0366] Table 1

[0367]

[0368]

[0369]

[0370] Comparative device preparation example 4: Comparative device 4

[0371] First, the ITO / Ag / ITO glass substrate was ultrasonically cleaned twice with deionized water for 20 minutes each time, and then ultrasonically cleaned with isopropyl alcohol, acetone and methanol for 20 minutes each, followed by exposure to ultraviolet light and ozone for 30 minutes, and finally placed in a vacuum evaporation equipment for use.

[0372] The following layers were evaporated layer by layer on the above-mentioned ITO / Ag / ITO glass substrate: a, HT-1 and p-1 (mass ratio of 100:7) as hole injection layer with a thickness of 25 nm; b, HT-1 as hole transport layer with a thickness of 35 nm; c, HOST-1, GH and Ir(ppy)2(m-bppy) (mass ratio of 47:47:6) as light-emitting layer with a thickness of 35 nm; d, TPBi as hole blocking layer with a thickness of 20 nm; e, NBphen and Liq (mass ratio of 1:1) as electron transport layer with a thickness of 20 nm; f, LiF as electron injection layer with a thickness of 0.1 nm; g, Mg and Ag (mass ratio of 7:3) as cathode with a thickness of 10 nm; h: CP-4 as covering layer with a thickness of 110 nm.

[0373] Comparative device preparation examples 5-6: Comparative devices 5-6

[0374] HOST-1 is replaced by HOST-2, and the other steps are the same as those in Comparative Device Preparation Example 3 to obtain Comparative Device 4.

[0375] Device Preparation Examples 35-68: Light-Emitting Devices 35-68

[0376] Light-emitting devices 35 to 68 are obtained by replacing HOST-1 with the carbazole indole derivatives of the present invention prepared in Synthesis Examples 2 to 35, and following the same other steps as in Comparative Device Preparation Example 3.

[0377] Table 2

[0378]

[0379]

[0380] The device data in Tables 1 and 2 demonstrate that the carbazolindole derivatives described herein, when used as host materials in OLED devices, significantly improve luminous efficiency, service life, and driving voltage. In summary, the carbazolindole derivatives provided by the present invention represent a class of high-performance OLED materials with promising application prospects.

[0381] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.

Claims

1. A carbazole indole derivative, characterized in that: The carbazole indole derivative has one of the following structures: Among them, the a 41 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said b 41 Each occurrence is identically or differently selected from 0, 1 or 2; said c 41 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; The R 41a Each occurrence is identically or differently selected from one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, and a substituted or unsubstituted phenyl group; The R 41 Each occurrence is the same or different selection from one of hydrogen atoms and deuterium atoms; One of Ar1 and Ar2 is selected from the following groups: Among them, the a 11 Each occurrence is identically or differently selected from 1, 2, 3, 4 or 5; said b 11 Each occurrence is identically or differently selected from 1, 2, 3 or 4; said c 11 Each occurrence is identically or differently selected from 1, 2 or 3; said d 11 Each occurrence is identically or differently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; The R 11 Each occurrence is selected, identically or differently, from a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, One of the following; The R 11a Each occurrence is identically or differently selected from one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, and a substituted or unsubstituted phenyl group; The R 12 Each occurrence is identically or differently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group; The R 13 One selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl; The other of Ar1 and Ar2 is selected from one of the following groups: Among them, the a 21 Each occurrence is identically or differently selected from 1, 2, 3, 4 or 5; said b 21 Each occurrence is identically or differently selected from 1, 2, 3 or 4; said c 21 Each occurrence is identically or differently selected from 1, 2, or 3; The R 21 Such as R 11 As stated; The L1 is selected from a single bond; The L2 to L3 are independently selected from a single bond or one of the following structures: Among them, the a 31 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 31 Each occurrence is identically or differently selected from 0, 1, 2 or 3; The R 31 Each occurrence is identically or differently selected from one of a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, and a substituted or unsubstituted tert-butyl group; Provided that the molecule contains one of the following groups: wherein said Z is selected from carbon atom or silicon atom, said Ar 101 Selected from single bonds, the Ar 102 ~Ar 104 is independently selected from substituted or unsubstituted methyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and the Ar 102 ~Ar 104 At least one of the following groups is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl; The term "substituted or unsubstituted" means not substituted or substituted with one or more substituents selected from the group consisting of a deuterium atom, a methyl group, and a deuterated methyl group. In the case of being substituted with multiple substituents, the multiple substituents may be the same or different.

2. The carbazoloindole derivative according to claim 1, characterized in that One of Ar1 and Ar2 is selected from the following groups: The other of Ar1 and Ar2 is selected from one of the following groups:

3. The carbazoloindole derivative according to claim 1, characterized in that described In the above, the Ar 101 Selected from single bonds, the Ar 102 ~Ar 104 is independently selected from one of substituted or unsubstituted methyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and the Ar 102 ~Ar 104 At least one of them is selected from substituted or unsubstituted phenyl groups.

4. The carbazoloindole derivative according to claim 1, characterized in that The carbazole indole derivative has one of the following structures: The R 41 Each occurrence is identically or differently selected from one of a hydrogen atom and a deuterium atom.

5. A carbazolindole derivative, characterized in that: The carbazole indole derivative is selected from one of the following compounds:

6. An organic electroluminescent device comprising an anode, a cathode, and an organic layer, wherein the organic layer comprises at least one of a hole transport region between the anode and the cathode, a light-emitting layer, an electron transport region, and a covering layer on the side of the cathode facing away from the anode, characterized in that: The organic layer includes a light-emitting layer, and the light-emitting layer contains one or more carbazolindole derivatives according to any one of claims 1 to 5.

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