CN116589470A

CN116589470A - Carbazolo indole derivative and organic electroluminescent device thereof

Info

Publication number: CN116589470A
Application number: CN202310559163.2A
Authority: CN
Inventors: 杜明珠; 周雯庭; 刘喜庆; 孙敬
Original assignee: Changchun Hyperions Technology Co Ltd
Current assignee: Changchun Hyperions Technology Co Ltd
Priority date: 2023-05-17
Filing date: 2023-05-17
Publication date: 2023-08-15

Abstract

The invention relates to the technical field of organic photoelectric materials, in particular to a carbazolo indole derivative and an organic electroluminescent device thereof. The carbazolo indole derivative provided by the invention has proper HOMO and LUMO, can effectively transfer energy to a guest material when being used as a host material of a light-emitting layer, has proper charge transmission performance, and can improve the injection efficiency of holes and electrons to the light-emitting layer, thereby improving the generation rate of excitons in the light-emitting layer, reducing the driving voltage of a device and improving the light-emitting efficiency of the device. Because the material has proper HOMO and LUMO, the material can be well matched with other organic functional layers, the interface transmission efficiency of charges is improved, the interface stability between the material and the adjacent organic functional layers is also improved, the thermal stability and chemical stability of the material are excellent, the ageing of a device can be delayed, and the service life of the device is further prolonged.

Description

Carbazolo indole derivative and organic electroluminescent device thereof

Technical Field

The invention relates to the technical field of organic photoelectric materials, in particular to a carbazolo indole derivative and an organic electroluminescent device thereof.

Background

An Organic Light-Emitting Diode (OLED) has the characteristics of Light and thin body, wide viewing angle, fast response speed, wide use temperature range, low energy consumption, high efficiency, good color purity, high definition, good flexibility, and the like, and has been widely used in the fields of illumination and display, and is considered as one of the display and illumination technologies with the most development prospects in the industry.

The classical OLED device is in a sandwich structure, a luminescent layer is sandwiched between two electrodes of a cathode and an anode, wherein the luminescent layer contains luminescent substances (guest materials), a certain working voltage is applied between the two electrodes, so that holes and electrons are respectively injected from the anode and the cathode and then reach the luminescent layer, excitons are generated by recombination, energy is released, the excitons migrate under the action of an electric field, energy is transferred to the luminescent substances, electrons in molecules of the luminescent substances migrate from a ground state to an excited state, and the electrons migrate from the excited state to the ground state again due to unstable excited states, thereby releasing the energy in the form of light and generating a luminescence phenomenon. In general, the Lowest Unoccupied Molecular Orbital (LUMO) of the host material is higher than the guest material, and the Highest Occupied Molecular Orbital (HOMO) of the host material is lower than the guest material. In order to improve the performance of the device, more organic functional layers are arranged between the anode and the light-emitting layer and between the cathode and the light-emitting layer, and a hole transmission area is generally arranged between the anode and the light-emitting layer and mainly plays roles in injecting and transmitting holes, and comprises a hole injection layer, a hole transmission layer, a light-emitting auxiliary layer, an electron blocking layer and the like; an electron transmission area is arranged between the cathode and the light-emitting layer, and mainly plays roles in injecting and transmitting electrons, and comprises an electron injection layer, an electron transmission layer, a hole blocking layer and the like.

In addition to the organic functional layer between the anode and the cathode, a cover layer is provided on the outside of the light-emitting side electrode (away from the non-light-emitting side electrode). In general, the cover layer has a higher refractive index, and can improve the light transmittance of the device, change the light emission direction, and the like, thereby improving the light emission efficiency, color purity, and the like of the device.

In order to further improve the light-emitting efficiency, color purity, and lifetime of OLED devices, it is necessary to develop host materials that have high energy level matching with guest materials and adjacent organic functional layers, proper charge transport properties, and excellent stability.

Disclosure of Invention

In order to solve the technical problems, the invention provides a carbazolo indole derivative which has proper charge mobility, proper HOMO and T1 values and good thermal stability and chemical stability, is used as a main material in an OLED device, can improve the luminous efficiency, service life and other performances of the OLED device, and has a structure that a group shown in a formula (I-A) and a group shown in a formula (I-B) are combined:

wherein X in formula (I-A) ₁ ～X ₈ Wherein adjacent two of the radicals are carbon and are combined with two of the radicals of the formula (I-B), the remainder being independently selected from nitrogen atoms or C-L ₁ -R ₁ Said X ₉ To X ₁₂ Independently selected from nitrogen atoms or C-L ₁ -R ₁ ；

Ar as described ₁ 、Ar ₂ Independently selected from one of 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 fusing a substituted or unsubstituted C6-C30 aromatic ring to a substituted or unsubstituted C3-C7 alicyclic ring, a substituted or unsubstituted C2-C30 heteroaryl group, a group represented by the formula (I-C), and Ar ₁ With Ar ₂ At least one of which is selected from the group represented by the formula (I-C):

wherein said at least one ofY is selected from the group consisting of an oxygen atom, a sulfur atom, and N-L ₄ -R ₂ 、CR ₃ R ₄ One of said R ₂ The same or different is selected from bond, substituted or unsubstituted aryl of C6-C30, monovalent group formed by fusing substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted alicyclic of C3-C7, substituted or unsubstituted heteroaryl of C2-C30, substituted or unsubstituted arylene of C6-C30, divalent group formed by fusing substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted alicyclic of C3-C7, and substituted or unsubstituted heteroarylene of C2-C30; said R is ₃ 、R ₄ And each occurrence is the same or different selected from one of bond, hydrogen atom, deuterium atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, monovalent group formed by fusing substituted or unsubstituted C6-C30 aryl ring and substituted or unsubstituted C3-C7 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 arylene, divalent group formed by fusing substituted or unsubstituted C6-C30 aryl ring and substituted or unsubstituted C3-C7 aliphatic ring, substituted or unsubstituted C2-C30 heteroarylene, or R ₃ 、R ₄ Capable of linking to form a substituted or unsubstituted C5-C10 alicyclic ring; when R is ₂ 、R ₃ Or R is ₄ When selected from bond, substituted or unsubstituted C6-C30 arylene, divalent group formed by fusing substituted or unsubstituted C6-C30 aromatic ring and substituted or unsubstituted C3-C7 alicyclic ring, and substituted or unsubstituted C2-C30 heteroarylene, R ₂ 、R ₃ Or R is ₄ And L is equal to ₂ Or L ₃ Are connected;

said Y ₁ ～Y ₈ Independently selected from nitrogen atoms or C-L ₅ -R ₅ ；

Said R is ₁ 、R ₅ Is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, and a substituted or unsubstituted C3-C10 cycloalkyl group One of substituted or unsubstituted C6-C30 aryl, monovalent group formed by fusing substituted or unsubstituted C6-C30 aryl ring and substituted or unsubstituted C3-C7 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, substituted or unsubstituted amino, and two adjacent R ₁ Or two adjacent R ₅ Capable of being linked to form one of a substituted or unsubstituted C5-C7 aliphatic ring, a substituted or unsubstituted C6-C14 aromatic ring, a substituted or unsubstituted C2-C10 heteroaromatic ring, and having at least two adjacent R ₁ To form one of 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, and a substituted or unsubstituted quinazoline ring;

the L is ₁ ～L ₅ Each occurrence of which is the same or different selected from one of single bond, substituted or unsubstituted arylene of C6-C30, bivalent group formed by fusing substituted or unsubstituted aromatic ring of C6-C30 and aliphatic ring of substituted or unsubstituted C3-C7, and substituted or unsubstituted heteroarylene of C4-C30;

Provided that the molecule contains at least one of the following groups:wherein Z is selected from a carbon atom or a silicon atom, ar is ₁₀₁ One selected from single bond, substituted or unsubstituted C6-C30 arylene, divalent group formed by fusing substituted or unsubstituted C6-C30 aromatic ring and substituted or unsubstituted C3-C7 alicyclic ring, substituted or unsubstituted C4-C30 heteroarylene, wherein Ar ₁₀₂ ～Ar ₁₀₄ 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 substituted or unsubstituted C6-C30 aromatic ring, and a substituted or unsubstituted C3-C7 aliphatic ringOne of fused monovalent groups, substituted or unsubstituted C2-C30 heteroaryl groups, and Ar ₁₀₂ ～Ar ₁₀₄ At least one of the substituted or unsubstituted C6-C30 aryl, the monovalent group formed by fusing the substituted or unsubstituted C6-C30 aryl ring and the substituted or unsubstituted C3-C7 alicyclic ring, and the substituted or unsubstituted C2-C30 heteroaryl.

The invention also provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer, wherein the organic layer comprises at least one layer of a hole transmission area, a luminescent layer, an electron transmission area and a covering layer on one side of the cathode, which is far away from the anode, between the anode and the cathode, and the organic layer contains more than one carbazole-indole derivative.

The beneficial effects are that:

the carbazolo indole derivative provided by the invention has proper HOMO and LUMO, can effectively transfer energy to a guest material when being used as a host material of a light-emitting layer, has proper charge transmission performance, and can improve the injection efficiency of holes and electrons to the light-emitting layer, thereby improving the generation rate of excitons in the light-emitting layer, reducing the driving voltage of a device and improving the light-emitting efficiency of the device. Because the material has proper HOMO and LUMO, the material can be well matched with other organic functional layers, the interface transmission efficiency of charges is improved, the interface stability between the material and the adjacent organic functional layers is also improved, the thermal stability and chemical stability of the material are excellent, the ageing of a device can be delayed, and the service life of the device is further prolonged.

Detailed Description

The following description of the embodiments of the present invention will be made more complete and obvious by the following description of the embodiments of the present invention, wherein the embodiments are described in some, but not all, of the embodiments of the present invention. All other embodiments, which can be made by a person skilled in the art without making any inventive effort, are intended to fall within the scope of the present invention.

In the compounds of the present invention, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes atoms in both its natural isotopic abundance and non-natural abundance. Taking hydrogen as an example, each hydrogen atom of all naturally occurring compounds contains about 0.0156 atomic% deuterium.

In the present invention, the use of "H" and "hydrogen atom" means that the hydrogen atom in the chemical structure contains no more than the natural abundance of deuterium or tritium atoms, for example, no more than 0.0156 atomic% deuterium. "D" and "deuterium atom" refer to any value having an abundance of deuterium content above natural abundance, e.g., above 0.1 atom%, above 1 atom%, above 10 atom%, e.g., where about 95 atom% is deuterium. "T" and "tritium atom" refer to any value where the abundance of tritium content is above natural abundance, e.g., greater than 0.1 atomic%, greater than 1 atomic%, greater than 10 atomic%, e.g., where about 95% is tritium. In the present invention, hydrogen not shown is omitted to indicate "H" or "hydrogen atom".

The halogen atom in the present invention means fluorine atom, chlorine atom, bromine atom and iodine atom.

As used herein, "silyl" refers to-SiH ₃ A group, the "substituted or unsubstituted silyl" refers to one or more H on the silyl group being substituted or unsubstituted with a substituent.

The alkyl group according to the present invention is a hydrocarbon group having at least one hydrogen atom in the alkane molecule, and may be a straight chain alkyl group or a branched chain alkyl group, and preferably has 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, but is not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl and the like; the branched alkyl group includes, but is not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, an isomeric group of n-pentyl, an isomeric group of n-hexyl, an isomeric group of n-heptyl, an isomeric group of n-octyl, an isomeric group of n-nonyl, an isomeric group of n-decyl, and the like. The alkyl group is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group.

Cycloalkyl according to the invention is a hydrocarbon radical formed by the removal of at least one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 5 to 10 carbon atoms. Examples may include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, and the like. The cycloalkyl group is preferably a cyclopentylalkyl group, a cyclohexenyl group, a 1-adamantyl group, a 2-adamantyl group, or a norbornyl group.

Cycloalkenyl according to the invention means hydrocarbon radicals formed by the removal of at least one hydrogen atom from the cycloolefin molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 5 to 10 carbon atoms. Examples may include, but are not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like. The cycloalkyl group is preferably a cyclopentenyl group or a cyclohexenyl group.

The heterocycloalkyl group according to the present invention is a group formed by dropping at least one hydrogen atom from a heterocyclic molecule having at least one heteroatom other than carbon atoms, and the heteroatom includes a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a selenium atom, a phosphorus atom, and the like, and is preferably a nitrogen atom, an oxygen atom, or a sulfur atom. Preferably from 1 to 3 heteroatoms, more preferably from 1 to 2 heteroatoms, particularly preferably 1 heteroatom. Preferably from 3 to 15, more preferably from 3 to 12, particularly preferably from 5 to 6, ring atoms. Examples may include, but are not limited to, oxiranyl, ethylidenyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, and the like. The heterocyclic group is preferably a tetrahydropyrrolyl group, a piperidyl group, a morpholinyl group, a thiomorpholinyl group, or a piperazinyl group.

Aryl in the present invention means that after one hydrogen atom is removed from the aromatic nucleus carbon of the aromatic compound molecule, a monovalent group is left, which may be a monocyclic aryl group, a polycyclic aryl group, a condensed ring aryl group, or a condensed group of an aryl group and an alicyclic 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 aryl refers to aryl having only one aromatic ring in the molecule, for example, phenyl, etc., but is not limited thereto; the polycyclic aryl group refers to an aryl group having two or more independent aromatic rings in the molecule, for example, biphenyl, terphenyl, etc., but is not limited thereto; the condensed ring aryl group refers to an aryl group having two or more aromatic rings in the molecule and condensed by sharing two adjacent carbon atoms with each other, for example, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylene, fluoranthryl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, and the like, but is not limited thereto. The aryl group is preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl.

Heteroaryl according to the present invention refers to the generic term for groups in which one or more aromatic nucleus carbon atoms in the aryl group are replaced by heteroatoms, including but 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, most preferably 3 to 12 carbon atoms, the attachment site of the heteroaryl group may be located on a ring-forming carbon atom, or on a ring-forming nitrogen atom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a fused ring heteroaryl group. The monocyclic heteroaryl group includes, but is not limited to, pyridyl, pyrimidinyl, triazinyl, furyl, thienyl, pyrrolyl, imidazolyl, and the like; the polycyclic heteroaryl group includes bipyridyl, bipyrimidinyl, phenylpyridyl, etc., but is not limited thereto; the fused ring heteroaryl group includes, but is not limited to, quinolinyl, isoquinolinyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, carbazolyl, benzocarbazolyl, acridinyl, 9, 10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiazinyl, and the like. The heteroaryl group is preferably a pyridyl group, a pyrimidyl group, a thienyl group, a furyl group, a benzothienyl group, a benzofuryl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a dibenzofuryl group, a dibenzothienyl group, a benzodibenzothienyl group, a benzodibenzofuryl group, a carbazolyl group, an acridinyl group, a phenoxazinyl group, a phenothiazinyl group, or a phenoxathiazide group.

The group formed by fusing the aromatic ring and the aliphatic ring refers to the general name that after the aromatic ring and the aliphatic ring (cycloalkyl, cycloalkenyl and cycloalkynyl) are fused together, one hydrogen atom is removed, and a monovalent group is left. The aromatic ring preferably has 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, which may include benzene, naphthalene, anthracene, phenanthrene, etc., but is not limited thereto; the alicyclic ring preferably has 3 to 9 carbon atoms, more preferably 5 to 7 carbon atoms, which may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclopropyne, cyclobutyne, cyclopentyne, cyclohexayne, cycloheptyne. Preferably, examples of the group in which the aromatic ring is condensed with the aliphatic ring may include, but are not limited to, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, and the like.

Arylene in the context of the present invention means an aryl group having two bonding sites, i.e., a divalent group. With respect to the description of aryl groups that may be applied, provided above, the difference is that arylene groups are divalent groups.

Heteroaryl, as used herein, means a heteroaryl group having two bonding sites, i.e., a divalent group. With respect to the description of heteroaryl groups that may be applied, provided above, the difference is that the heteroarylene group is a divalent group.

The divalent group formed by fusing an aromatic ring and an aliphatic ring in the present invention refers to a group formed by fusing an aromatic ring and an aliphatic ring having two bonding sites, that is, a divalent group. Regarding the description thereof, which can be applied to the group formed by fusing an aromatic ring and an aliphatic ring provided above, the difference is that a divalent group formed by fusing an aromatic ring and an aliphatic ring is a divalent group.

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

The term "substituted or unsubstituted" as used herein means that it is not substituted or substituted with one or more substituents selected from the group consisting of: deuterium atom, halogen atom, amino group, cyano group, nitro group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C3-C30 cycloalkenyl group, substituted or unsubstituted C3-C30 heterocycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C6-C60 aryloxy group, substituted or unsubstituted C2-C60 heteroaryl group, substituted or unsubstituted silyl group, preferably deuterium atom, halogen atom, cyano group, nitro group, C1-C12 alkyl group, C3-C12 cycloalkyl group, C3-C12 cycloalkenyl group, C3-C12 heterocycloalkyl group, C6-C30 aryl group, C3-C30 heteroaryl group, substituted or unsubstituted silyl group, in the case of being substituted with a plurality of substituents, the plurality of substituents may be the same as or different from each other; preferably, it means not substituted or substituted with one or more substituents selected from the group consisting of: deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuteromethyl group, ethyl group, deuteroethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, deuterated tert-butyl group, cyclopropane group, methyl-substituted cyclopropane group, ethyl-substituted cyclopropane group, deuterated cyclopropane group, cyclobutane group, methyl-substituted cyclobutane group, ethyl-substituted cyclobutane group, deuterated cyclobutane group, cyclopentane group, methyl-substituted cyclopentane group, ethyl-substituted cyclopentane group, deuterated cyclopentane group, cyclohexane group, methyl-substituted cyclohexane group, ethyl-substituted cyclohexane group, n-propyl-substituted cyclohexane group, n-butyl-substituted cyclohexane group, cyclohexane-substituted cyclohexane group, deuterated cyclohexane group, cycloheptane group, cyclopentene group, methyl-substituted cyclopentene group 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 piperazinyl, ethyl substituted piperazinyl, phenyl substituted piperazinyl, naphthyl substituted piperazinyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracenyl, deuterated anthracenyl, phenanthryl, deuterated phenanthryl, triphenylenyl, pyrenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzothienyl, trimethylsilyl, triphenylsilyl, in the case of being substituted with a plurality of substituents, the plurality of substituents may be the same or different from each other.

In this specification, when the position of a substituent or attachment site on a ring is not fixed, it means that it can be attached to any of the optional sites of the ring. For example, the number of the cells to be processed,can indicate-> Can represent Can indicate-> And so on.

In this specification, when a substituent or linkage site is located across two or more rings, it is meant that it may be attached to either of the two or two rings, in particular to either of the respective selectable sites of the rings. For example, the number of the cells to be processed,can indicate-> Can indicate-> Can indicate->And so on.

The linking to form a ring structure (e.g., to form a saturated or unsaturated C3-C10 carbocycle, to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbocycle) as described herein means that the individual groups are linked to each other by chemical bonds and optionally form double/triple bonds, and may constitute aromatic groups, as exemplified below:

in the present invention, the ring formed by the connection may be an aromatic ring system, an aliphatic ring system or a ring system formed by the fusion of both, and the ring formed by the connection may 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, cyclopentaacene, cyclohexene, cyclohexane acene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.

In the present specification, "at least one" includes one, two, three, four, five, six, seven, eight, or more.

The invention provides a carbazolo indole derivative, which has a structure that a group shown in a formula (I-A) and a formula (I-B) are combined:

wherein each occurrence of Y is selected from the group consisting of an oxygen atom, a sulfur atom, and N-L ₄ -R ₂ 、CR ₃ R ₄ One of said R ₂ The same or different is selected from bond, substituted or unsubstituted aryl of C6-C30, monovalent group formed by fusing substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted alicyclic of C3-C7, substituted or unsubstituted heteroaryl of C2-C30, substituted or unsubstituted arylene of C6-C30, divalent group formed by fusing substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted alicyclic of C3-C7, and substituted or unsubstituted heteroarylene of C2-C30; said R is ₃ 、R ₄ And each occurrence is the same or different selected from one of bond, hydrogen atom, deuterium atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, monovalent group formed by fusing substituted or unsubstituted C6-C30 aryl ring and substituted or unsubstituted C3-C7 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 arylene, divalent group formed by fusing substituted or unsubstituted C6-C30 aryl ring and substituted or unsubstituted C3-C7 aliphatic ring, substituted or unsubstituted C2-C30 heteroarylene, or R ₃ 、R ₄ Capable of linking to form a substituted or unsubstituted C5-C10 alicyclic ring; when R is ₂ 、R ₃ Or R is ₄ When selected from bond, substituted or unsubstituted C6-C30 arylene, divalent group formed by fusing substituted or unsubstituted C6-C30 aromatic ring and substituted or unsubstituted C3-C7 alicyclic ring, and substituted or unsubstituted C2-C30 heteroarylene, R ₂ 、R ₃ Or R is ₄ And L is equal to ₂ Or L ₃ Are connected;

Said R is ₁ 、R ₅ At each time of occurrence of this, the process is completed, is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group,Nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, monovalent group formed by fusing a substituted or unsubstituted C6-C30 aromatic ring with a substituted or unsubstituted C3-C7 alicyclic ring, one of substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, substituted or unsubstituted amino, and two adjacent R ₁ Or two adjacent R ₅ Capable of being linked to form one of a substituted or unsubstituted C5-C7 aliphatic ring, a substituted or unsubstituted C6-C14 aromatic ring, a substituted or unsubstituted C2-C10 heteroaromatic ring, and having at least two adjacent R ₁ To form one of 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, and a substituted or unsubstituted quinazoline ring;

provided that the molecule contains at least one of the following groups:wherein Z is selected from a carbon atom or a silicon atom, ar is ₁₀₁ One selected from single bond, substituted or unsubstituted C6-C30 arylene, divalent group formed by fusing substituted or unsubstituted C6-C30 aromatic ring and substituted or unsubstituted C3-C7 alicyclic ring, substituted or unsubstituted C4-C30 heteroarylene, wherein Ar ₁₀₂ ～Ar ₁₀₄ 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-upper-halfOne of an aryl group of C30, a monovalent group formed by fusing 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, and the Ar ₁₀₂ ～Ar ₁₀₄ At least one of the substituted or unsubstituted C6-C30 aryl, the monovalent group formed by fusing the substituted or unsubstituted C6-C30 aryl ring and the substituted or unsubstituted C3-C7 alicyclic ring, and the substituted or unsubstituted C2-C30 heteroaryl.

Preferably, said Ar ₁ 、Ar ₂ 、R ₁ 、R ₅ At least one of which contains the following groups:wherein Z is selected from a carbon atom or a silicon atom, ar is ₁₀₁ One selected from single bond, substituted or unsubstituted C6-C30 arylene, divalent group formed by fusing substituted or unsubstituted C6-C30 aromatic ring and substituted or unsubstituted C3-C7 alicyclic ring, substituted or unsubstituted C4-C30 heteroarylene, wherein Ar ₁₀₂ ～Ar ₁₀₄ Independently selected from one of 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 fusing a substituted or unsubstituted C6-C30 aromatic ring with a substituted or unsubstituted C3-C7 alicyclic ring, a substituted or unsubstituted C2-C30 heteroaryl group, and ₁₀₂ ～Ar ₁₀₄ At least one of the substituted or unsubstituted C6-C30 aryl, the monovalent group formed by fusing the substituted or unsubstituted C6-C30 aryl ring and the substituted or unsubstituted C3-C7 alicyclic ring, and the substituted or unsubstituted C2-C30 heteroaryl.

Preferably, the substituents in said "substituted or unsubstituted" are selected from deuterium atoms; a halogen atom; cyano group; straight-chain or branched-chain alkyl of 1 to 12 carbon atoms substituted or unsubstituted with one or more of the group consisting of deuterium atom, halogen atom, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, phenyl group, deuterated phenyl group, methyl-substituted phenyl group, tert-butyl-substituted phenyl group, halogen-substituted phenyl group, cyano-substituted phenyl group, adamantyl-substituted phenyl group, norbornyl-substituted phenyl group, naphthyl group, deuterated naphthyl group, anthryl group, phenanthryl group, biphenyl group, pyridyl group, pyrimidinyl group, dibenzofuranyl group, dibenzothienyl group; a C3-C12 cycloalkyl group which is substituted or unsubstituted with one or more of the group consisting of deuterium atom, halogen atom, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, t-butyl group, phenyl group, naphthyl group and biphenyl group; a C3-C12 cycloalkenyl group which is substituted or unsubstituted with one or more of the group consisting of deuterium atom, halogen atom, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, t-butyl group, phenyl group, naphthyl group and biphenyl group; a C6-C30 aryl group which is substituted or unsubstituted with one or more of the group consisting of deuterium atom, halogen atom, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, t-butyl group, phenyl group, naphthyl group and biphenyl group; a C2-C30 heteroaryl group which is substituted or unsubstituted with one or more of the group consisting of deuterium atom, halogen atom, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, t-butyl group, phenyl group, naphthyl group and biphenyl group; a group formed by fusing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, wherein the substituted or unsubstituted C6-C30 aromatic ring is one or more selected from the group consisting of deuterium atom, halogen atom, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, t-butyl group, phenyl group, naphthyl group and biphenyl group; one or more substituted or unsubstituted silyl groups selected from the group consisting of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, phenyl, deuterated phenyl, methyl-substituted phenyl, t-butyl-substituted phenyl, halogen-substituted phenyl, cyano-substituted phenyl, adamantyl-substituted phenyl, norbornyl-substituted phenyl, naphthyl, deuterated naphthyl, anthryl, phenanthryl, biphenyl, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothienyl, wherein one or more of the substituents may be substituted or unsubstituted, and when a plurality of substituents are present, the plurality of substituents may be the same or different, and when a plurality of substituents are present, two adjacent substituents may be linked to form a substituted or unsubstituted saturated or unsaturated C3 to C7 carbocyclic ring.

Preferably, the substituents in said "substituted or unsubstituted" are selected from deuterium atoms; a fluorine atom; cyano group; methyl substituted or unsubstituted one or more of the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, phenyl, deuterated phenyl, methyl-substituted phenyl, t-butyl-substituted phenyl, halogen-substituted phenyl, cyano-substituted phenyl, adamantyl-substituted phenyl, norbornyl-substituted phenyl, naphthyl, deuterated naphthyl, anthracenyl, phenanthryl, biphenyl, pyridinyl, pyrimidinyl, dibenzofuranyl, dibenzothiophenyl; an ethyl group; n-propyl; an isopropyl group; n-butyl; sec-butyl; an isobutyl group; a tertiary butyl group; deuterated methyl; deuterated isopropyl; deuterated tert-butyl; a cyclopropane group substituted or unsubstituted with one or more of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, phenyl group, naphthyl group, biphenyl group; a cyclobutyl group substituted or unsubstituted by one or more than one of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, phenyl group, naphthyl group and biphenyl group; a cyclopentylalkyl group substituted or unsubstituted with one or more than one of the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, phenyl group, naphthyl group, biphenyl group; a cyclohexyl group substituted or unsubstituted with one or more of the group consisting of methyl, ethyl, isopropyl, n-butyl, t-butyl, phenyl, naphthyl, and biphenyl; a cyclopropenyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, phenyl group, naphthyl group, biphenyl group; a cyclobutenyl group substituted or unsubstituted with one or more of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, phenyl group, naphthyl group, biphenyl group; cyclopentenyl substituted or unsubstituted with one or more from the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, t-butyl, phenyl, naphthyl, biphenyl; cyclohexenyl substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, t-butyl, phenyl, naphthyl, biphenyl; an adamantyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, phenyl group, naphthyl group, biphenyl group; norbornyl substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, phenyl group, naphthyl group, biphenyl group; phenyl substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, t-butyl, deuterated methyl, deuterated isopropyl, deuterated t-butyl, adamantyl, norbornyl; naphthyl substituted or unsubstituted by one or more of the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; an anthracene group substituted or unsubstituted with one or more than one of the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, t-butyl, deuterated methyl, deuterated isopropyl, deuterated t-butyl, adamantyl, and norbornyl; phenanthryl substituted or unsubstituted by one or more of the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; a triphenylene group substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, deuterated methyl group, deuterated isopropyl group, deuterated t-butyl group, adamantyl group, and norbornyl group; a fluorenyl group substituted or unsubstituted with one or more than one of the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, deuterated methyl group, deuterated isopropyl group, deuterated t-butyl group, adamantyl group, norbornyl group, phenyl group, naphthyl group, biphenyl group; a dibenzofuranyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, deuterated methyl group, deuterated isopropyl group, deuterated t-butyl group, adamantyl group, and norbornyl group; a dibenzothienyl group substituted with one or more than one of deuterium atom, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; a carbazolyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, deuterated methyl group, deuterated isopropyl group, deuterated t-butyl group, adamantyl group, norbornyl group, phenyl group, naphthyl group, biphenyl group; a pyridyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, deuterated methyl group, deuterated isopropyl group, deuterated t-butyl group, adamantyl group, and norbornyl group; pyrimidinyl substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, t-butyl, deuterated methyl, deuterated isopropyl, deuterated t-butyl, adamantyl, norbornyl; a pyrazinyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, deuterated methyl group, deuterated isopropyl group, deuterated t-butyl group, adamantyl group, and norbornyl group; a pyridazinyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, deuterated methyl group, deuterated isopropyl group, deuterated t-butyl group, adamantyl group, and norbornyl group; a quinolinyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, deuterated methyl group, deuterated isopropyl group, deuterated t-butyl group, adamantyl group, and norbornyl group; an isoquinolinyl group substituted or unsubstituted with one or more from the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, deuterated methyl group, deuterated isopropyl group, deuterated t-butyl group, adamantyl group, and norbornyl group; a quinoxalinyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, deuterated methyl group, deuterated isopropyl group, deuterated t-butyl group, adamantyl group, and norbornyl group; a quinazolinyl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, deuterated methyl group, deuterated isopropyl group, deuterated t-butyl group, adamantyl group, and norbornyl group; an indanyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, deuterated methyl group, deuterated isopropyl group, deuterated t-butyl group, adamantyl group, and norbornyl group; a tetrahydronaphthyl group substituted or unsubstituted with one or more than one of the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, deuterated methyl group, deuterated isopropyl group, deuterated t-butyl group, adamantyl group, and norbornyl group; one or more substituted or unsubstituted silyl groups selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, phenyl, deuterated phenyl, methyl-substituted phenyl, t-butyl-substituted phenyl, halogen-substituted phenyl, cyano-substituted phenyl, adamantyl-substituted phenyl, norbornyl-substituted phenyl, naphthyl, deuterated naphthyl, anthracenyl, phenanthryl, biphenyl, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothienyl, wherein one or more of the substituents is/are the same or different when the substituents are plural, and two adjacent substituents may be linked to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbocyclic ring when the substituents are plural.

Preferably, said R ₁ 、R ₅ Each occurrence is selected identically or differently from hydrogen atoms; deuterium atoms; a fluorine atom; cyano group; an isopropyl group; deuterated isopropyl; a tertiary butyl group; deuterated tert-butyl; a cyclopentylalkyl group; deuterated cyclopentylalkyl; a cyclohexenyl group; deuterated cyclohexenyl; an adamantyl group substituted or unsubstituted with one or more of deuterium atom, methyl group, ethyl group, isopropyl group, tert-butyl group; norbornyl substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl group, ethyl group, isopropyl group, tert-butyl group; phenyl substituted or unsubstituted with one or more of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, naphthyl group, deuterated naphthyl group, anthryl group, phenanthryl group; one of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuteromethyl group, isopropyl group, deuterisopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, deuterated phenyl group, naphthyl group, deuterated naphthyl groupA substituted or unsubstituted naphthyl group; biphenyl substituted or unsubstituted with one or more of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, and norbornyl group; an anthracene group substituted or unsubstituted with one or more than one 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; phenanthryl substituted or unsubstituted by one or more of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, adamantyl group, norbornyl group, phenyl group, and naphthyl group; triphenylene; deuterated triphenylene; a fluorenyl group substituted or unsubstituted with one or more than one of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuteromethyl 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 spirobifluorenyl group substituted or unsubstituted with one or more than one of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuteromethyl 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 pyridyl group; deuterated pyridyl; pyrimidinyl; deuterated pyrimidinyl; a triazine group substituted or unsubstituted with one or more selected from the group consisting of phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl; a quinolinyl group substituted or unsubstituted with one or more of deuterium atom, phenyl group, and naphthyl group; an isoquinolinyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, phenyl group and naphthyl group; dibenzofuranyl; deuterated dibenzofuranyl; dibenzothienyl; deuterated dibenzothienyl; phenyl carbazolyl; One of them.

Preferably, there are at least two adjacentR ₁ To form deuterium atom, fluorine atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted cyclohexenyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted norbornyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted spirobifluorenyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothienyl group, substituted or unsubstituted carbazolyl group,One or more substituted or unsubstituted ones of the following structures: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring.

Preferably, there are at least two adjacent R ₁ To form a group consisting of deuterium, fluorine, cyano, methyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, naphthyl, pyridyl, pyrimidinyl,One of the following substituted or unsubstituted structures: benzene ring, naphthalene ring, pyridine ring, pyrimidine ring.

Preferably, there are two adjacent R ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring.

Preferably, there are two adjacent R ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, and quinoline ringAn isoquinoline ring, a quinoxaline ring, a quinazoline ring, and two other adjacent R ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring.

Preferably, said Ar ₁ With Ar ₂ One of the groups represented by the formula (I-C) is selected from one of the groups represented by the following:

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Wherein, a is as follows ₁₁ Each occurrence is identically or differently selected from 1, 2, 3, 4 or 5; said b ₁₁ Each initial acquaintance is selected from 1, 2, 3 or 4 identically or differently; the said c ₁₁ Each occurrence is identically or differently selected from 1, 2 or 3; d is as follows 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 identically or differently selected from 1 or 2; g is as described ₁₁ Each occurrence is identically or differently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said h ₁₁ Each occurrence is identically or differently selected from 0 or 1;

said R is ₁₁ At each occurrence, the same or notA substituent selected from 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 cyclopentyl group, a substituted or unsubstituted cyclohexenyl 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 triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, One of the following;

said R is ₁₂ Each occurrence of which is the same or different 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 cyclopentylalkyl group, a substituted or unsubstituted cyclohexenyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted norbornyl group;

said R is ₁₃ Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, 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 quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, and,

One of them.

Ar as described ₁ With Ar ₂ Is selected from one of the following groups:

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wherein, a is as follows 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; the said c ₂₁ Each occurrence is identically or differently selected from 1, 2 or 3; d is as follows 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 identically or differently selected from 1 or 2; g is as described 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.e ₂₁ Each occurrence is identically or differently selected from 0 or 1;

said R is ₂₁ For example R ₁₁ The said; said R is ₂₂ For example R ₁₂ The said; said R is ₂₃ For example R ₁₃ Said method.

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

Preferably, said Ar ₁ With Ar ₂ Is selected from one of the following groups:

preferably Ar ₁ With Ar ₂ Is selected from one of the following groups:

ar as described ₁ With Ar ₂ Is selected from one of the following groups:

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preferably Ar ₁ With Ar ₂ Is selected from one of the following groups:

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preferably, the saidWherein Ar is as described ₁₀₁ Selected from the group consisting of 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 azorylene groupOne of the pyridyl groups, ar ₁₀₂ ～Ar ₁₀₄ Independently 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, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, and ₁₀₂ ～Ar ₁₀₄ at least one of the substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, and substituted or unsubstituted pyrimidinyl.

Preferably, said Ar ₁₀₁ One selected from single bond, phenylene, naphthylene and biphenylene, the Ar ₁₀₂ ～Ar ₁₀₄ Independently selected from one of methyl, isopropyl, tert-butyl, phenyl, deuterated phenyl, fluorine atom-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-dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, N-phenylcarbazolyl, pyridyl, pyrimidinyl, and Ar ₁₀₂ ～Ar ₁₀₄ At least one selected from the group consisting of phenyl, deuterated phenyl, fluorine atom-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-dimethylfluorenyl, 9-diphenylfluorenyl, dibenzofuranyl, dibenzothienyl, N-phenylcarbazolyl, pyridyl, and pyrimidinyl.

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

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more preferably, said Ar ₁₀₁ One selected from the following structures:

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

more preferably, said Ar ₁₀₂ ～Ar ₁₀₄ At least one (one, two or three) of which is selected from one of the groups shown below, and the rest is independently selected from one of methyl, isopropyl, tert-butyl or the groups shown below:

preferably, in the present invention, theOne selected from the group consisting of: />

Preferably, said L ₁ ～L ₅ Independently selected from a single bond or one of the structures shown below:

wherein, a is as follows 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 said c ₃₁ Each occurrence is identically or differently selected from 0, 1 or 2; d is as follows 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;

Said R is ₃₁ Each occurrence of which is the same or different, is 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 cyclopentanyl group, a substituted or unsubstituted cyclohexenyl 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 anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl 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.

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preferably, the carbazolo indole derivative contains one, two, three, four, five and six

More preferably, the carbazoloindole derivative contains one, two or three

More preferably, ar in the carbazoloindole derivative ₁ Contains one ofAnd/or Ar ₂ Contains one of

Preferably, X ₁ -X ₁₂ Up to five of which are selected from N; more preferably, X ₁ -X ₁₂ Up to three of which are selected from N; more preferably, X ₁ -X ₁₂ At most two of which are selected from N; also preferably, X ₁ -X ₁₂ At most one of which is selected from N.

Preferably, X ₁ -X ₄ At most two of them are selected from N, X ₅ -X ₈ At most one of them is selected from N, X ₉ -X ₁₂ At most two of which are selected from N; more, thePreferably, X ₁ -X ₄ At most one of them is selected from N, X ₅ -X ₈ At most one of them is selected from N, X ₉ -X ₁₂ At most one of which is selected from N.

Preferably, the carbazolo indole derivative has one of the structures shown in formulas (II-A) to (II-E):

wherein, X is ₁ ～X ₁₂ 、Ar ₁ 、Ar ₂ 、L ₂ 、L ₃ All as described herein.

Preferably, in the formula (II-A) and the formula (II-B), the X ₁ ～X ₄ At least two adjacent R ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring; and/or X ₅ ～X ₆ R adjacent to each other ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring; and/or X ₉ ～X ₁₂ At least two adjacent R ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring.

Also preferably, in the formula (II-A), the formula (II-B), the X ₁ ～X ₂ R adjacent to each other ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring; and/or X ₃ ～X ₄ R adjacent to each other ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring,Quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring; and/or X ₅ ～X ₆ R adjacent to each other ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring; and/or X ₉ ～X ₁₀ R adjacent to each other ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring; and/or X ₁₁ ～X ₁₂ R adjacent to each other ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring.

Preferably, in the formulae (II-C) and (II-D), the X ₁ ～X ₄ At least two adjacent R ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring; and/or X ₉ ～X ₁₂ At least two adjacent R ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring.

Also preferred, in formula (II-C), formula (II-D), the X ₁ ～X ₂ R adjacent to each other ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring; and/or X ₃ ～X ₄ R adjacent to each other ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring; and/or X ₉ ～X ₁₀ R adjacent to each other ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring; and/or X ₁₁ ～X ₁₂ R adjacent to each other ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring.

Preferably, in formula (II-E), the X ₁ ～X ₄ At least two adjacent R ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring; and/or X ₇ ～X ₈ R adjacent to each other ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring; and/or X ₉ ～X ₁₂ At least two adjacent R ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring.

Also preferably, in formula (II-E), the X ₁ ～X ₂ R adjacent to each other ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring; and/or X ₃ ～X ₄ R adjacent to each other ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring; and/or X ₇ ～X ₈ R adjacent to each other ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring,Quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring; and/or X ₉ ～X ₁₀ R adjacent to each other ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring; and/or X ₁₁ ～X ₁₂ R adjacent to each other ₁ And are linked to form one of the substituted or unsubstituted structures described below: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring.

Preferably, the carbazolo indole derivative has one of the structures shown in formulas (III-1) to (III-32):

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wherein, a is as follows ₄₁ Each occurrence is identically or differently selected from 1, 2, 3, 4, 5 or 6; said b ₄₁ Each occurrence is identically or differently selected from 1 or 2; the said c ₄₁ Each occurrence is identically or differently selected from 1, 2, 3 or 4; d is as follows ₄₁ Each occurrence is identically or differently selected from 1, 2, 3, 4, 5, 6, 7 or 8;

said R is ₄₁ R in the present invention ₁₁ The same;

ar as described ₁ 、Ar ₂ 、L ₂ 、L ₃ All as described herein;

provided that the molecule contains at least one of the following groups:wherein Z is selected from a carbon atom or a silicon atom, ar is ₁₀₁ Arylene selected from single bond, substituted or unsubstituted C6 to C30One of a divalent group formed by fusing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring and a substituted or unsubstituted C4-C30 heteroarylene group, wherein Ar is ₁₀₂ ～Ar ₁₀₄ Independently selected from one of 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 fusing a substituted or unsubstituted C6-C30 aromatic ring with a substituted or unsubstituted C3-C7 alicyclic ring, a substituted or unsubstituted C2-C30 heteroaryl group, and ₁₀₂ ～Ar ₁₀₄ At least one of the substituted or unsubstituted C6-C30 aryl, the monovalent group formed by fusing the substituted or unsubstituted C6-C30 aryl ring and the substituted or unsubstituted C3-C7 alicyclic ring, and the substituted or unsubstituted C2-C30 heteroaryl.

Preferably, each R ₁₁ 、R ₂₁ 、R ₄₁ At least one of them is selected from

More preferably, each R ₁₁ 、R ₂₁ 、R ₄₁ One or two of them are selected from

More preferably, each R ₁₁ One of them is selected fromAnd/or each R ₂₁ One of them is selected from

Preferably, the carbazolo indole derivative has one of the structures shown in formulas (IV-A) to (IV-V):

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wherein, a is as follows ₄₁ 、b ₄₁ 、c ₄₁ 、R ₄₁ 、Ar ₁ 、Ar ₂ 、L ₂ 、L ₃ All as described herein;

y is selected from the group consisting of an oxygen atom, a sulfur atom, and N-L ₄ -R ₂ 、CR ₃ R ₄ One of said Y ₁ ～Y ₈ Independently selected from nitrogen atoms or C-L ₅ -R ₅ Said R is ₂ 、R ₃ 、R ₄ 、R ₅ 、L ₄ 、L ₅ All as described herein;

provided that the molecule contains at least one of the following groups:wherein Z is selected from a carbon atom or a silicon atom, ar is ₁₀₁ One selected from single bond, substituted or unsubstituted C6-C30 arylene, divalent group formed by fusing substituted or unsubstituted C6-C30 aromatic ring and substituted or unsubstituted C3-C7 alicyclic ring, substituted or unsubstituted C4-C30 heteroarylene, wherein Ar ₁₀₂ ～Ar ₁₀₄ Independently selected from one of 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 fusing a substituted or unsubstituted C6-C30 aromatic ring with a substituted or unsubstituted C3-C7 alicyclic ring, a substituted or unsubstituted C2-C30 heteroaryl group, and ₁₀₂ ～Ar ₁₀₄ at least one of the substituted or unsubstituted C6-C30 aryl, the monovalent group formed by fusing the substituted or unsubstituted C6-C30 aryl ring and the substituted or unsubstituted C3-C7 alicyclic ring, and the substituted or unsubstituted C2-C30 heteroaryl.

Preferably, the method comprises the steps of,i.e. the radicals of the formula (I-C) are as described in the present invention.

More preferably, each R ₁₁ One of them is selected fromAnd/or each R ₂₁ One of them is selected from->

Preferably, the carbazoloindole derivative has one of the structures shown in formulas (V-1) to (V-48):

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wherein, a is as follows ₄₁ 、b ₄₁ 、c ₄₁ 、R ₄₁ 、Ar ₁ 、Ar ₂ 、L ₂ 、L ₃ 、Y、Y ₁ ～Y ₈ 、Z、Ar ₁₀₁ ～Ar ₁₀₄ All as described herein. Preferably, the method comprises the steps of,i.e. the radicals of the formula (I-C) are as described in the present invention.

Preferably, the carbazolo indole derivative has one of the structures shown in formulas (VI-1) to (VI-38):

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provided that the molecule contains at least one of the following groups:wherein Z is selected from carbon atoms or silicon atoms

Son, ar as described ₁₀₁ One selected from single bond, substituted or unsubstituted C6-C30 arylene, divalent group formed by fusing substituted or unsubstituted C6-C30 aromatic ring and substituted or unsubstituted C3-C7 alicyclic ring, substituted or unsubstituted C4-C30 heteroarylene, wherein Ar ₁₀₂ ～Ar ₁₀₄ Independently selected from one of 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 fusing a substituted or unsubstituted C6-C30 aromatic ring with a substituted or unsubstituted C3-C7 alicyclic ring, a substituted or unsubstituted C2-C30 heteroaryl group, and ₁₀₂ ～Ar ₁₀₄ at least one of the substituted or unsubstituted C6-C30 aryl, the monovalent group formed by fusing the substituted or unsubstituted C6-C30 aryl ring and the substituted or unsubstituted C3-C7 alicyclic ring, and the substituted or unsubstituted C2-C30 heteroaryl.

More preferably, each R ₁₁ One of them is selected fromAnd/or each R ₂₁ One of them is selected from->Preferably, the carbazolo indole derivative has one of the structures shown in formulas (VII-1) to (VII-44):

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provided that the molecule contains at least one of the followingThe group:wherein Z is selected from a carbon atom or a silicon atom, ar is ₁₀₁ One selected from single bond, substituted or unsubstituted C6-C30 arylene, divalent group formed by fusing substituted or unsubstituted C6-C30 aromatic ring and substituted or unsubstituted C3-C7 alicyclic ring, substituted or unsubstituted C4-C30 heteroarylene, wherein Ar ₁₀₂ ～Ar ₁₀₄ Independently selected from one of 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 fusing a substituted or unsubstituted C6-C30 aromatic ring with a substituted or unsubstituted C3-C7 alicyclic ring, a substituted or unsubstituted C2-C30 heteroaryl group, and ₁₀₂ ～Ar ₁₀₄ At least one of the substituted or unsubstituted C6-C30 aryl, the monovalent group formed by fusing the substituted or unsubstituted C6-C30 aryl ring and the substituted or unsubstituted C3-C7 alicyclic ring, and the substituted or unsubstituted C2-C30 heteroaryl.

Preferably, the carbazolo indole derivative has one of the structures shown in formulas (VIII-1) to (VIII-66):

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wherein, a is as follows ₄₁ 、b ₄₁ 、c ₄₁ 、R ₄₁ 、Ar ₁ 、L ₂ 、L ₃ 、Y、Y ₁ ～Y ₈ 、Z、Ar ₂₀₁ ～Ar ₂₀₄ All as described herein. Most preferably, the carbazoloindole derivative is selected from one of the following compounds:

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the above list only shows some specific structural forms of the carbazoloindole derivatives according to the present invention, but the present invention is not limited to the chemical structures shown, and substituents are included as defined in the present invention, even when the carbazoloindole derivatives are based on the formulae (I-A), (I-B) and (I-C).

The carbazolo indole derivative provided by the invention can be prepared by the following synthetic route:

wherein said Z ₁ 、Z ₂ Independently selected from a chlorine atom, a bromine atom, or an iodine atom;

said X ₁ ～X ₁₂ 、L ₂ 、L ₃ 、Ar ₁ 、Ar ₂ All as described herein.

In the synthetic route, the carbazoloindole derivative can be obtained by C-N coupling reaction of the compound (M) and the halides (N1) and (N2). The order of the reaction of the compound (M) with the halides (N1) and (N2) is not limited, and the compound (M) may be reacted with (N1) and then (N2), or may be reacted with (N2) and then (N1).

The reaction route is not particularly limited as long as it is of a reaction type commonly used in organic synthesis, and the reaction conditions (e.g., selection of the kind, amount, and order and method of addition of the reaction solvent, catalyst, ligand, base, etc.). The preparation method has the advantages of easily available raw materials, simple preparation process and excellent yield. The present invention may also be synthesized by using other conventional reaction types in organic synthesis, and is not particularly limited, and the above are merely examples of synthetic routes.

Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer contains more than one of the carbazolo indole derivatives.

Preferably, the light-emitting layer comprises a guest material and a host material, and the host material contains more than one of the carbazole-indole derivatives.

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

The hole transport region according to the present invention includes at least one of a hole injection layer, a hole transport layer, and a light emitting auxiliary layer.

The hole injection layer of the present invention may have a single-layer structure formed of a single material, or may have a single-layer structure or a multi-layer structure formed of different materials. Triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and derivatives thereof, phthalocyanine derivatives, axial vinyl compounds, and other substances having high hole injection properties, for example, 4',4″ -tris [ 2-naphthylphenylamino ] triphenylamine (2-TNATA), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-Hexaazabenzophenanthrene (HATCN), copper phthalocyanine (CuPC), 2,3,5, 6-tetrafluoro-7, 7', 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.

The hole transport layer of the present invention may have a single layer structure of a single material, or may have a single layer structure or a multilayer structure of different materials. Triarylamine compounds can be used, as can other hole mobilities at 10 ^-6 cm ² Examples of the material above/Vs include, but are not limited to, N, N ' -diphenyl-N, N ' -bis (3-methylphenyl) -1,1' -biphenyl-4, 4' -diamine (TPD), N, N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), 4' -tris (N, N-diphenylamino) triphenylamine (TDATA), and the above-mentioned compounds HT-1 to HT-19.

The light-emitting auxiliary layer of the present invention may have a single-layer structure composed of a single substance, or may have a single-layer structure or a multi-layer structure composed of different substances. Triarylamine compounds, spirofluorene derivatives and dibenzofuran derivatives may be used, and other materials having appropriate HOMO and T1 energy levels may be used, and TPD, NPB, N, 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' -biphenyl ] -4-yl) -N- (9, 9-dimethyl-9H-furan-2-yl) -9,9 '-spirobifluorene-2-amine, N-bis ([ 1,1' -biphenyl ] -4-yl) -3'- (dibenzo [ b, d ] furan-4-yl) - [1,1' -biphenyl ] -4-amine, compounds HT-1-HT-19 as indicated above, but are not limited thereto.

The light emitting layer according to the present invention includes a guest material and a host material, and a dual host material formed of two host materials may be used. As the guest material, fluorescent compounds such as pyrene derivatives, fluoranthene derivatives, aromatic amine derivatives and the like can be used, and examples thereof include 10- (2-benzothiazolyl) -2,3,6, 7-tetrahydro-1, 7-tetramethyl-1H, 5H,11H- [1]Benzopyran [6,7,8-ij ]]Quinolizin-11-one (C545T), 4' -bis (9-ethyl-3-carbazolyl vinyl) -1,1' -biphenyl (BCzVBi), 4' -bis [4- (di-p-tolylamino) styryl]Examples of the metal complex such as an iridium complex, an osmium complex, and a platinum complex, which may be used as a phosphorescent light-emitting material, include bis (4, 6-difluorophenylpyridine-N, C2) picolinated iridium (FIrpic) and tris (2-phenylpyridine) iridium (Ir (ppy) ₃ ) Bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy) ₂ (acac)) and the like. The host material is preferably a material having higher LUMO and lower HOMO than the guest material, for example, a metal complex such as an aluminum complex or zinc complex, an oxadiazole derivative, a benzoxazole derivative, a heterocyclic compound such as a benzothiazole derivative or a benzimidazole derivative, a condensed aromatic compound such as a carbazole derivative or an anthracene derivative, an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative, and examples thereof include Alq ₃ BAlq, TPBI, TPD, 4 '-bis (9-Carbazole) Biphenyl (CBP), 4',4 "-tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (2-naphthyl) Anthracene (ADN), and the carbazoloindole derivatives according to the present invention are not limited thereto.

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

The electron injection layer of the invention can be a single layer structure formed by a single substance, can also be a single layer structure or a multi-layer structure formed by different substances, and can be selected from one or more of the following substances: alkali metal, alkaline earth metal, alkali metal halide, alkaline earth metal halide, alkali metal oxide, alkaline earth metal oxide, alkali metal salt, alkaline earth metal salt, and other substances having high electron injection properties. Examples can be cited as Li, ca, sr, liF, csF, caF ₂ 、BaO、Li ₂ CO ₃ 、CaCO ₃ 、Li ₂ C ₂ O ₄ 、Cs ₂ C ₂ O ₄ 、CsAlF ₄ LiOx, yb, tb, etc., but is not limited thereto.

The electron transporting layer according to the present invention may have a single layer structure, or may have a single layer structure or a multilayer structure of different materials, and aluminum complex, lithium complex, beryllium complex, zinc complex, oxazole derivative, benzoxazole derivative, thiazole derivative, benzothiazole derivative, imidazole derivative, benzimidazole derivative, carbazole derivative, phenanthroline derivative, polymer compound, etc. having high electron transporting property may be used, and examples thereof include 8-hydroxyquinoline aluminum (Alq ₃ ) Bis (10-hydroxybenzo [ h ]]Quinoline) beryllium (BeBq ₂ ) Bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-hydroxy) aluminum (BAlq), 2- (4-biphenyl) -5-Phenyloxadiazole (PBD), but is not limited thereto.

The hole blocking layer of the present invention may have a single layer structure formed of a single material, or may have a single layer structure or a multilayer structure formed of different materials. The material selected requires a T1 energy level higher than the light emitting layer so that energy loss from the light emitting layer is blocked. In addition, the HOMO energy level of the selected material is lower than that of the main body material of the light-emitting layer, so that the hole blocking effect is realized. Further, the electron mobility of the hole blocking layer material used was 10 ^-6 cm ² and/Vs, facilitating electron transport. One or more of the following may be selected: aluminum (Al)Complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, high molecular compounds, and the like. Examples include, but are not limited to, 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBI), BAlq, and the like.

The anode of the 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 alloys thereof, or a transparent or semitransparent layer structure with high work function, such as Indium Tin Oxide (ITO), indium zinc oxide (ZnO), aluminum Zinc Oxide (AZO), indium Gallium Oxide (IGO), indium oxide (In) ₂ O ₃ ) Or tin oxide (SnO) ₂ ) The layer structure is formed according to the type of the device to be manufactured, if the device to be manufactured is a bottom emission device (anode side emits light), a transparent or semitransparent anode is required to be manufactured, and if the device to be manufactured is a top emission device (cathode side emits light), a reflecting anode is required to be manufactured.

The cathode of the invention can be a thin film with low work function, which is made of lithium, calcium, lithium fluoride/aluminum, silver, magnesium silver alloy, etc., and can be made into a reflecting electrode, a transparent electrode or a semitransparent electrode by adjusting the thickness of the film, if a bottom emission device is required to be prepared, a reflecting cathode is required to be prepared, if a top emission device is required to be prepared, and a transparent or semitransparent cathode is required to be prepared.

The cover layer according to the present invention may have a single layer structure of a single substance, or may have a single layer structure or a multilayer structure of different substances. The material for the covering layer may be an organic or inorganic substance having an appropriate refractive index, and may be, for example, a metal halide, oxide, nitride, oxynitride, sulfide, selenide, aromatic hydrocarbon compound, heteroaromatic compound, aromatic amine compound, or the like, and LiF, csF, mgF is exemplified ₂ 、CaF ₂ 、CsCl、CuI、V ₂ O ₅ 、WO ₃ 、MoO ₃ 、TiO ₂ 、ZrO、ZnO、SiO ₂ 、SiN、ZnS、Alq ₃ Compound CP-1, compound CP-2, compound CP-3, compound CP-4, arylamine compound according to the invention, but not limited thereto.

Preferably, the organic layer comprises a hole transport region, a light emitting layer and an electron transport region, and the light emitting layer contains more than one of the carbazoloindole derivatives.

Preferably, the organic layer comprises a hole transport region, a light emitting layer, an electron transport region and a cover layer, and the light emitting layer contains more than one carbazole-indole derivative.

Preferably, the organic layer comprises 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 more than one carbazole-indole derivative.

Preferably, the organic layer comprises 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 more than one of the carbazoloindole derivatives.

Preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer and an electron injection layer, and the light-emitting layer contains more than one carbazole-indole derivative.

Preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer, and the light-emitting layer contains more than one carbazole-indole derivative.

Preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cover layer, and the light emitting layer contains more than one carbazole-indole derivative.

Preferably, the organic layer comprises 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 cover layer, and the light emitting layer contains more than one carbazole-indole derivative.

Preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cover layer, and the light-emitting layer contains more than one carbazole-indole derivative.

Preferably, the organic layer includes a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a capping layer, and the light emitting auxiliary layer contains one or more of the aromatic amine compounds of the present invention.

Preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cover layer, and the light-emitting layer contains more than one of the carbazole-indole derivatives.

The organic layers, cathode, anode and cover layer can be prepared by any one of vacuum evaporation, ink-jet printing, sputtering, plasma, ion plating, spin coating, dipping, screen printing and the like, and the thickness of each layer is not particularly limited, so that good device performance can be obtained. Each of the organic layers described above is preferably prepared using a method of vacuum evaporation, inkjet printing or spin coating.

The thickness of each of the organic layer and the cover layer is usually 5nm to 100. Mu.m, preferably 10nm to 200nm. The thickness of the anode and cathode is adjusted according to the desired transparency.

The organic electroluminescent device provided by the invention can be applied to the fields of illumination, display and the like, and can be specifically exemplified by a large-size display such as a smart phone display screen, a tablet personal computer display screen, an intelligent wearable device display screen, a television and the like, VR, an automobile tail lamp and the like.

The technical scheme and technical effects of the present invention will be further described below with examples and comparative examples.

The mass spectrum of the compound of the invention uses a G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer of the Wolts company, england, chloroform as a solvent;

the elemental analysis was carried out using a Vario EL cube organic elemental analyzer from Elementar, germany, and the sample mass was 5 to 10mg.

Synthesis example 1: synthesis of Compound N

Synthesis of Compound N-180:

a-180 (20.00 mmol,8.31 g), B-180 (20.00 mmol,3.13 g), potassium carbonate (30.00 mmol,4.15 g), pd were added to the flask under nitrogen ₂ (dba) ₃ (0.20 mmol,0.18 g) 180ml toluene/ethanol/water (2:1:1) mixed solvent was added and the mixture was stirred and the above reactant system was heated under reflux for 6h. After the reaction, cooling to room temperature, adding toluene, separating each phase, washing the toluene phase with distilled water three times, drying with anhydrous magnesium sulfate, rotationally evaporating to concentrate the solvent, cooling to crystallize, suction filtering, recrystallizing the obtained solid with toluene to obtain a compound N-180 (6.97 g, 78%), wherein the purity of the solid detected by HPLC is more than or equal to 99.71%. Mass spectrum m/z:446.1267 (theory: 446.1258).

According to the above synthesis method, other compounds N required in the present invention were synthesized, and the relevant raw materials are shown in table 101:

Table 101:

synthesis example 2: synthesis of Compound 27

To the reaction vessel were added 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 t-butoxide (15.00 mmol,1.44 g) and 50ml o-xylene, and the mixture was stirred under reflux for 4.5h. 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. And then the o-xylene is recrystallized to obtain compound 27 (4.85 g, 61%), and the purity of the solid detected by HPLC is more than or equal to 99.96%. Mass spectrum m/z:794.3225 (theory: 794.3235). Theoretical element content (%) C ₅₉ H ₃₄ D ₄ N ₂ O: c,89.14; h,5.32; n,3.52. Measured element content (%): c,89.13; h,5.33; n,3.51.

Synthesis example 3: synthesis of Compound 47

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-47 to obtain compound 47 (5.59 g, 63%), and the purity of the solid was not less than 99.97% by HPLC. Mass spectrum m/z:886.3333 (theory: 886.3320). Theoretical element content (%) C ₆₅ H ₃₈ D ₄ N ₂ S: c,88.00; h,5.23; n,3.16. Measured element content (%): c,88.01; h,5.25; n,3.15.

Synthesis example 4: synthesis of Compound 83

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-83 to obtain compound 83 (5.13 g, 59%) whose purity by HPLC was not less than 99.95%. Mass spectrum m/z:869.3718 (theory: 869.3708). Theoretical element content (%) C ₆₅ H ₃₉ D ₄ N ₃ : c,89.73; h,5.44; n,4.83. Measured element content (%): c,89.75; h,5.45; n,4.81.

Synthesis example 5: synthesis of Compound 120

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-120 to obtain compound 120 (5.64 g, 65%), and the purity of the solid was not less than 99.98% by HPLC detection. Mass spectrum m/z:866.3675 (theory: 866.3661). Theoretical element content (%) C ₆₆ H ₄₆ N ₂ : c,91.42; h,5.35; n,3.23. Measured element content (%): c,91.41; h,5.38; n,3.22.

Synthesis example 6: synthesis of Compound 172

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-172 and N-27 was replaced with equimolar A-180 to obtain compound 172 (5.65 g, 64%), and the purity of the solid was not less than 99.97% by HPLC detection. Mass spectrum m/z:882.3055 (theory: 882.3066). Theoretical element content (%) C ₆₄ H ₄₂ N ₂ OSi: c,87.04; h,4.79; n,3.17. Measured element content (%): c,87.06; h,4.78; n,3.18.

Synthesis example 7: synthesis of Compound 180

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-180 and N-27 was replaced with equimolar N-180 to obtain compound 180 (5.83 g, 66%), and the purity of the solid was not less than 99.95% by HPLC detection. Mass spectrum m/z:882.3058 (theory: 882.3066). Theoretical element content (%) C ₆₄ H ₄₂ N ₂ OSi: c,87.04; h,4.79; n,3.17. Measured element content (%): c,87.05; h,4.77; n,3.16.

Synthesis example 8: synthesis of Compound 241

According to the preparation method of Synthesis example 2, M-27 was replaced with equimolar M-241 and N-27 was replaced with equimolar A-692, to obtain compound 241 (5.47 g, 62%), and the purity of the solid was not less than 99.96% by HPLC detection. Mass spectrum m/z:881.3218 (theory: 881.3226). Theoretical element content (%) C ₆₄ H ₄₃ N ₃ Si: c,87.14; h,4.91; n,4.76. Measured element content (%): c,87.15; h,4.92; n,4.75.

Synthesis example 9: synthesis of Compound 361

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-361 and N-27 was replaced with equimolar N-361, to obtain compound 361 (4.69 g, 58%) having a purity of not less than 99.98% by HPLC. Mass spectrum m/z:807.2718 (theory: 807.2706). Theoretical element content (%) C ₅₇ H ₃₇ N ₃ OSi: c,84.73; h,4.62; n,5.20. Measured element content (%): c,84.72; h,4.63; n,5.21.

Synthesis example 10: synthesis of Compound 384

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-384 and N-27 was replaced with equimolar N-384 to obtain compound 384 (5.40 g, 60%), and the purity of the solid was not less than 99.97% by HPLC. Mass spectrum m/z:898.2823 (theory: 898.2838). Theoretical element content (%) C ₆₄ H ₄₂ N ₂ SSi: c,85.49; h,4.71; n,3.12. Measured element content (%): c,85.47; h,4.69; n,3.13.

Synthesis example 11: synthesis of Compound 459

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-459 and N-27 was replaced with equimolar A-180 to obtain compound 459 (5.39 g, 61%) having a purity of not less than 99.97% as measured by HPLC. Mass spectrum m/z:882.3075 (theory: 882.3066). Theoretical element content (%) C ₆₄ H ₄₂ N ₂ OSi: c,87.04; h,4.79; n,3.17. Measured element content (%): c,87.05; h,4.76; n,3.16.

Synthesis example 12: synthesis of Compound 467

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-467 and N-27 was replaced with equimolar A-692, to obtain compound 467 (5.54 g, 68%), and the purity of the solid was not less than 99.96% by HPLC. Mass spectrum m/z:813.3185 (theory: 813.3193). Theoretical element content (%) C ₅₈ H ₃₁ D ₇ N ₂ OSi: c,85.57; h,5.57; n,3.44. Measured element content (%): c,85.54; h,5.56; n,3.46.

Synthesis example 13: synthesis of Compound 509

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According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-509 and N-27 was replaced with equimolar N-361, to obtain compound 509 (4.76 g, 59%) having a purity of not less than 99.95% as measured by HPLC. Mass spectrum m/z:806.2742 (theory: 806.2753). Theoretical element content (%) C ₅₈ H ₃₈ N ₂ OSi: c,86.32; h,4.75; n,3.47. Measured element content (%): c,86.38; h,4.72; n,3.48.

Synthesis example 14: synthesis of Compound 511

According to the preparation method of Synthesis example 2, M-27 was replaced with equimolar M-511 and N-27 was replaced with equimolar N-361, to give Compound 511 (5.23 g, 61%), and the purity of the solid was not less than 99.97% by HPLC detection. Mass spectrum m/z:856.2918 (theory: 856.2910). Theoretical element content (%) C ₆₂ H ₄₀ N ₂ OSi: c,86.88; h,4.70; n,3.27. Measured element content (%): c,86.85; h,4.71; n,3.28.

Synthesis example 15: synthesis of Compound 541

According to the preparation method of Synthesis example 2, N-27 was replaced with equimolar N-541 to obtain compound 541 (6.00 g, 64%), and the purity of the solid was not less than 99.95% by HPLC. Mass spectrum m/z:936.3485 (theory: 936.3474). Theoretical element content (%) C ₆₈ H ₄₀ D ₄ N ₂ OSi: c,87.15; h,5.16; n,2.99. Measured element content (%): c,87.16; h,5.18; n,2.98.

Synthesis example 16: synthesis of Compound 567

According to the preparation method of Synthesis example 2, M-27 was replaced with equimolar M-467 and N-27 was replaced with equimolar N-567, to obtain compound 567 (6.05 g, 65%), and the purity of the solid was not less than 99.98% by HPLC detection. Mass spectrum m/z:929.3833 (theory: 929.3819). Theoretical element content (%) C ₆₇ H ₃₉ D ₇ N ₂ OSi: c,86.51; h,5.74; n,3.01. Measured element content (%): c,86.53; h,5.71; n,3.00.

Synthesis example 17: synthesis of Compound 634

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-634, N-27 was replaced with equimolar N-384, to obtain compound 634 (5.26 g, 63%), and the purity of the solid was not less than 99.97% by HPLC detection. Mass spectrum m/z:834.3288 (theory: 834.3278). Theoretical element content (%) C ₅₈ H ₂₆ D ₁₂ N ₂ SSi: c,83.41; h,6.03; n,3.35. Measured element content (%): c,83.43; h,6.05; n,3.33.

Synthesis example 18: synthesis of Compound 665

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-47 and N-27 was replaced with equimolar A-180 to obtain compound 665 (6.05 g, 67%), and the purity of the solid was not less than 99.96% by HPLC detection. Mass spectrum m/z:902.3075 (theory: 902.3089). Theoretical element content (%) C ₆₄ H ₃₈ D ₄ N ₂ SSi: c,85.11; h,5.13; n,3.10. Measured element content (%): c,85.10; h,5.12; n,3.11.

Synthesis example 19: synthesis of Compound 678

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-678 and N-27 was replaced with equimolar N-384 to give compound 678 (5.02 g, 61%) having a purity of not less than 99.97% by HPLC. Mass spectrum m/z:822.2538 (theory: 822.2525). Theoretical element content (%) C ₅₈ H ₃₈ N ₂ SSi: c,84.64; h,4.65; n,3.40. Measured element content (%): c,84.66; h,4.66; n,3.38.

Synthesis example 20: synthesis of Compound 692

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-692 and N-27 was replaced with equimolar N-692, to obtain compound 692 (5.82 g, 64%), and the purity of the solid was not less than 99.98% by HPLC detection. Mass spectrum m/z:908.3577 (theory: 908.3587). Theoretical element content (%) C ₆₇ H ₄₈ N ₂ Si: c,88.51; h,5.32; n,3.08. Measured element content (%): c,88.53; h,5.31; n,3.10.

Synthesis example 21: synthesis of Compound 798

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-509 and N-27 was replaced with equimolar N-798 to give compound 798 (5.73 g, 60%) having a purity of not less than 99.96% as measured by HPLC. Mass spectrum m/z:954.3443 (theory: 954.3430). Theoretical element content (%) C ₇₁ H ₄₆ N ₂ Si: c,89.27; h,4.85; n,2.93. Measured element content (%): c,89.28; h,4.83; n,2.95.

Synthesis example 22: synthesis of Compound 849

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-849 and N-27 was replaced with equimolar A-180 to obtain compound 849 (5.94 g, 67%), and the purity of the solid was not less than 99.97% by HPLC. Mass spectrum m/z:885.3488 (theory: 885.3477). Theoretical element content (%) C ₆₄ H ₃₉ D ₄ N ₃ Si: c,86.74; h,5.35; n,4.74. Measured element content (%): c,86.72; h,5.33; n,4.75.

Synthesis example 23: synthesis of Compound 876

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-876 and N-27 was replaced with equimolar N-876, to give compound 876 (5.47 g, 61%) and a solid purity of not less than 99.95% by HPLC. Mass spectrum m/z:896.2868 (theory: 896.2859). Theoretical element content (%) C ₆₄ H ₄₀ N ₂ O ₂ Si: c,85.69; h,4.49; n,3.12. Measured element content (%): c,85.71; h,4.50; n,3.11.

Synthesis example 24: synthesis of Compound 908

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-908 and N-27 was replaced with equimolar A-692, to obtain compound 908 (5.40 g, 63%), and the purity of the solid was not less than 99.96% by HPLC detection. Mass spectrum m/z:856.2923 (theory: 856.2910). Theoretical element content (%) C ₆₂ H ₄₀ N ₂ OSi: c,86.88; h,4.70; n,3.27. Measured element content (%): c,86.85; h,4.72; n,3.30.

Synthesis example 25: synthesis of Compound 931

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-931 and N-27 was replaced with equimolar N-931 to obtain compound 931 (5.76 g, 66%), and the purity of the solid was not less than 99.98% by HPLC detection. Mass spectrum m/z:872.2695 (theory: 872.2681). Theoretical element content (%) C ₆₂ H ₄₀ N ₂ SSi: c,85.29; h,4.62; n,3.21. Measured element content (%): c,85.28; h,4.59; n,3.23.

Synthesis example 26: synthesis of Compound 942

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-942 and N-27 was replaced with equimolar A-180 to obtain compound 942 (5.59 g, 64%), and the purity of the solid was not less than 99.97% by HPLC detection. Mass spectrum m/z:872.2690 (theory: 872.2681). Theoretical element content (%) C ₆₂ H ₄₀ N ₂ SSi: c,85.29; h,4.62; n,3.21. Measured element content (%): c,85.27; h,4.63; n,3.24.

Synthesis example 27: synthesis of Compound 971

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-971 and N-27 was replaced with equimolar A-180 to obtain compound 971 (5.48 g, 62%), and the purity of the solid was not less than 99.96% by HPLC. Mass spectrum m/z:882.3442 (theory: 882.3430). Theoretical element content (%) C ₆₅ H ₄₆ N ₂ Si: c,88.40; h,5.25; n,3.17. Measured element content (%): c,88.42; h,5.28; n,3.14.

Synthesis example 28: synthesis of Compound 975

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-975 and N-27 was replaced with equimolar N-975, to give compound 975 (5.78 g, 65%), and the purity of the solid was not less than 99.98% by HPLC detection. Mass spectrum m/z:888.3908 (theory: 888.3900). Theoretical element content (%) C ₆₅ H ₅₂ N ₂ Si: c,87.80; h,5.89; n,3.15. Measured element content (%): c,87.85; h,5.88; n,3.14.

Synthesis example 29: synthesis of Compound 984

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-984 and N-27 was replaced with equimolar A-692, to obtain compound 984 (5.64 g, 61%), and the purity of the solid was not less than 99.97% by HPLC detection. Mass spectrum m/z:924.3891 (theory: 924.3900). Theoretical element content (%) C ₆₈ H ₅₂ N ₂ Si: c,88.27; h,5.66; n,3.03. Measured element content (%): c,88.28; h,5.67; n,3.02.

Synthesis example 30: synthesis of Compound 1044

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-1044 and N-27 was replaced with equimolar N-1044, to obtain compound 1044 (5.39 g, 59%), and the purity of the solid was not less than 99.96% by HPLC detection. Mass spectrum m/z:912.2638 (theory: 912.2631). Theoretical element content (%) C ₆₄ H ₄₀ N ₂ OSSi: c,84.18; h,4.42; n,3.07. Measured element content (%): c,84.16; h,4.44; n,3.08.

Synthesis example 31: synthesis of Compound 1057

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-1044 and N-27 was replaced with equimolar N-1057, to obtain compound 1057 (5.25 g, 65%), and the purity of the solid was not less than 99.97% by HPLC detection. Mass spectrum m/z:807.2718 (theory: 807.2706). Theoretical element content (%) C ₅₇ H ₃₇ N ₃ OSi: c,84.73; h,4.62; n,5.20. Measured element content (%): c,84.72; h,4.61; n,5.21.

Synthesis example 32: synthesis of Compound 1085

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-1085 and N-27 was replaced with equimolar N-1085, to give compound 1085 (5.60 g, 60%), and the purity of the solid was not less than 99.96% by HPLC detection. Mass spectrum m/z:932.3595 (theory: 932.3587). Theoretical element content (%) C ₆₉ H ₄₈ N ₂ Si: c,88.80; h,5.18; n,3.00. Measured element content (%): c,88.85; h,5.16; n,2.99.

Synthesis example 33: synthesis of Compound 1159

According to the preparation method of Synthesis example 2, M-27 was replaced with equimolar M-931 and N-27 was replaced with equimolar N-361, to obtain compound 1159 (5.84 g, 64%), and the purity of the solid was not less than 99.98% by HPLC detection. Mass spectrum m/z:912.2623 (theory: 912.2631). Theoretical element content (%) C ₆₄ H ₄₀ N ₂ OSSi: c,84.18; h,4.42; n,3.07. Measured element content (%): c,84.17; h,4.43; n,3.08.

Synthesis example 34: synthesis of Compound 1166

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-47 and N-27 was replaced with equimolar N-1166, to obtain compound 1166 (5.53 g, 71%), and the purity of the solid was not less than 99.93% by HPLC. Mass spectrum m/z:778.2763 (theory: 78.2776). Theoretical element content (%) C ₅₄ H ₃₄ D ₄ N ₂ SSi: c,83.25; h,5.43; n,3.60. Measured element content (%) C,83.22; h,5.41; n,3.64.

Synthesis example 35: synthesis of Compound 1172

According to the preparation method of synthetic example 2, M-27 was replaced with equimolar M-459 and N-27 was replaced with equimolar N-1172, to obtain compound 1172 (5.75 g, 70%), and the purity of the solid was not less than 99.94% by HPLC detection. Mass spectrum m/z 820.2930 (theory: 820.2910). Theoretical element content (%) C ₅₉ H ₄₀ N ₂ OSi: c,86.31; h,4.91; n,3.41. Measured element content (%): c,86.28; h,4.94; n,3.42.

The organic materials in the device preparation examples are purified by sublimation, and the purity is over 99.99 percent. The ITO glass substrate and the ITO/Ag/ITO glass substrate used in the device preparation example are all purchased in the market.

The following are other compounds used in the device preparation examples in addition to the carbazoloindole derivatives described in the present invention:

test software, a computer, a K2400 digital source meter from Keithley company, U.S. and a PR788 spectral scanning luminance meter from Photo Research, U.S. are combined into a combined IVL test system, and the device prepared by the invention is tested at atmospheric pressure and room temperature at a current density of 15mA/cm ² Light-emitting efficiency and driving voltage at the time. The lifetime of the devices prepared according to the invention (decay of brightness to 95% of the initial brightness) was tested using the Mcscience M6000 OLED lifetime test system at atmospheric pressure and room temperature. The test results are shown in tables 1 and 2.

Comparative device preparation example 1: contrast device 1

Firstly, the ITO/Ag/ITO glass substrate is ultrasonically cleaned by deionized water for 2 times, each time for 20 minutes, then sequentially ultrasonically cleaned by isopropanol, acetone and methanol for 20 minutes respectively, then exposed to ultraviolet rays and ozone for 30 minutes, and finally placed in a vacuum evaporation device for standby.

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

Comparative device preparation examples 2 to 3: contrast devices 2 to 3

HOST-1 was replaced with HOST-2, and the other steps were the same as those of comparative device preparation 1, to obtain comparative device preparation 2.

Device preparation examples 1 to 34: light emitting devices 1 to 34

HOST-1 was replaced with the carbazoloindole derivatives of the present invention prepared in Synthesis examples 2 to 35, and the other steps were the same as those of comparative device preparation example 1, thereby obtaining light-emitting devices 1 to 34.

TABLE 1

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Comparative device preparation example 4: contrast device 4

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

Comparative device preparation examples 5 to 6: contrast devices 5 to 6

The comparative device 4 was obtained by replacing HOST-1 with HOST-2 and performing the same procedure as in comparative device preparation 3.

Device preparation examples 35 to 68: light emitting devices 35 to 68

HOST-1 was replaced with the carbazoloindole derivatives of the present invention prepared in Synthesis examples 2 to 35, and the other steps were the same as those of comparative device preparation example 3, thereby obtaining light-emitting devices 35 to 68.

TABLE 2

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The device data in tables 1 and 2 show that the carbazoloindole derivative provided by the invention is used as a main material and applied to an OLED device, so that the luminous efficiency, the service life and the driving voltage are improved well. In conclusion, the carbazolo indole derivatives provided by the invention are OLED materials with excellent performance, and have good application prospects.

It should be noted that while the invention has been particularly described with reference to individual embodiments, those skilled in the art may make various modifications in form or detail without departing from the principles of the invention, which modifications are also within the scope of the invention.

Claims

1. A carbazoloindole derivative having a structure in which a group represented by the formula (I-a) is bonded to a group represented by the formula (I-B):

wherein each occurrence of Y is selected from the group consisting of an oxygen atom, a sulfur atom, and N-L ₄ -R ₂ 、CR ₃ R ₄ One of said R ₂ The radicals are selected identically or differently from the bonds, substituted or unsubstituted aryl radicals of from 6 to 30 carbon atoms, substituted or unsubstituted aryl rings of from 6 to 30 carbon atoms and substituted or unsubstituted C3-ultrahigh for each occurrenceOne of a monovalent group formed by fusing an aliphatic ring of C7, a substituted or unsubstituted heteroaryl group of C2 to C30, a substituted or unsubstituted arylene group of C6 to C30, a divalent group formed by fusing an aromatic ring of C6 to C30, which is substituted or unsubstituted, with an aliphatic ring of C3 to C7, and a substituted or unsubstituted heteroarylene group of C2 to C30; said R is ₃ 、R ₄ And each occurrence is the same or different selected from one of bond, hydrogen atom, deuterium atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, monovalent group formed by fusing substituted or unsubstituted C6-C30 aryl ring and substituted or unsubstituted C3-C7 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 arylene, divalent group formed by fusing substituted or unsubstituted C6-C30 aryl ring and substituted or unsubstituted C3-C7 aliphatic ring, substituted or unsubstituted C2-C30 heteroarylene, or R ₃ 、R ₄ Capable of linking to form a substituted or unsubstituted C5-C10 alicyclic ring; when R is ₂ 、R ₃ Or R is ₄ When selected from bond, substituted or unsubstituted C6-C30 arylene, divalent group formed by fusing substituted or unsubstituted C6-C30 aromatic ring and substituted or unsubstituted C3-C7 alicyclic ring, and substituted or unsubstituted C2-C30 heteroarylene, R ₂ 、R ₃ Or R is ₄ And L is equal to ₂ Or L ₃ Are connected;

Said R is ₁ 、R ₅ Each occurrence is identically or differently selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, 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 fusing a substituted or unsubstituted C6-C30 aromatic ring with a substituted or unsubstituted C3-C7 alicyclic ring, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, and two adjacent R' s ₁ Or two adjacent R ₅ Capable of being linked to form one of a substituted or unsubstituted C5-C7 aliphatic ring, a substituted or unsubstituted C6-C14 aromatic ring, a substituted or unsubstituted C2-C10 heteroaromatic ring, and having at least two adjacent R ₁ To form one of 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, and a substituted or unsubstituted quinazoline ring;

provided that the molecule contains at least one of the following groups:wherein Z is selected from a carbon atom or a silicon atom, ar is ₁₀₁ One selected from single bond, substituted or unsubstituted C6-C30 arylene, divalent group formed by fusing substituted or unsubstituted C6-C30 aromatic ring and substituted or unsubstituted C3-C7 alicyclic ring, substituted or unsubstituted C4-C30 heteroarylene, wherein Ar ₁₀₂ ～Ar ₁₀₄ Independently selected from one of 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 fusing a substituted or unsubstituted C6-C30 aromatic ring with a substituted or unsubstituted C3-C7 alicyclic ring, a substituted or unsubstituted C2-C30 heteroaryl group, and ₁₀₂ ～Ar ₁₀₄ At least one monovalent group selected from the group consisting of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C6-C30 aromatic rings and substituted or unsubstituted C3-C7 alicyclic rings, substituted or unsubstitutedOne of the substituted C2-C30 heteroaryl groups.

2. The carbazoloindole derivative according to claim 1, wherein Ar ₁ 、Ar ₂ 、R ₁ 、R ₅ At least one of which contains the following groups:wherein Z is selected from a carbon atom or a silicon atom, ar is ₁₀₁ One selected from single bond, substituted or unsubstituted C6-C30 arylene, divalent group formed by fusing substituted or unsubstituted C6-C30 aromatic ring and substituted or unsubstituted C3-C7 alicyclic ring, substituted or unsubstituted C4-C30 heteroarylene, wherein Ar ₁₀₂ ～Ar ₁₀₄ Independently selected from one of 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 fusing a substituted or unsubstituted C6-C30 aromatic ring with a substituted or unsubstituted C3-C7 alicyclic ring, a substituted or unsubstituted C2-C30 heteroaryl group, and ₁₀₂ ～Ar ₁₀₄ at least one of the substituted or unsubstituted C6-C30 aryl, the monovalent group formed by fusing the substituted or unsubstituted C6-C30 aryl ring and the substituted or unsubstituted C3-C7 alicyclic ring, and the substituted or unsubstituted C2-C30 heteroaryl.

3. The carbazoloindole derivative according to claim 1, wherein Ar ₁ With Ar ₂ One of the groups represented by the formula (I-C) is selected from one of the groups represented by the following:

said R is ₁₁ Each occurrence of which is the same or different and is selected from 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 cyclohexenyl 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 anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, and a substituted or unsubstituted dibenzofuranyl group Substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl,One of the following;

said R is ₁₃ Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, 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 quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, and,One of the following;

ar as described ₁ With Ar ₂ Is selected from one of the following groups:

Wherein, a is as follows 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; the said c ₂₁ Each occurrence is identically or differently selected from 1, 2 or 3; d is as follows ₂₁ The same or different at each occurrenceSelected 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 identically or differently selected from 1 or 2; g is as described 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.e ₂₁ Each occurrence is identically or differently selected from 0 or 1;

4. The carbazoloindole derivative according to claim 1, characterized in that the carbazoloindole derivative isWherein Ar is as described ₁₀₁ One 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 pyrimidinylene group, and the Ar ₁₀₂ ～Ar ₁₀₄ Independently 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, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, and ₁₀₂ ～Ar ₁₀₄ at least one selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzofuranylAn unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group.

5. The carbazoloindole derivative according to claim 1, wherein L is ₁ ～L ₅ Independently selected from a single bond or one of the structures shown below:

6. The carbazoloindole derivative of claim 1, wherein the carbazoloindole derivative has one of the structures of formulas (II-a) - (II-E):

wherein, X is ₁ ～X ₁₂ 、Ar ₁ 、Ar ₂ 、L ₂ 、L ₃ All as claimed in claim 1.

7. The carbazoloindole derivative according to claim 1, which has one of the structures represented by the formulas (III-1) to (III-32) and (VI-1) to (VI-38):

wherein, a is as follows 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; the said c ₄₁ Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; d is as follows ₄₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

said R is ₄₁ The groups are, for each occurrence, identically or differently selected from hydrogen atoms, deuterium atoms, fluorine atoms, cyano groups, substituted or unsubstituted methyl groups, substituted or unsubstituted isopropyl groups, substituted or unsubstituted tert-butyl groups, substituted or unsubstituted cyclopentylalkyl groups, substituted or unsubstituted cyclohexenyl groups, substituted or unsubstituted adamantyl groups, substitutedOr one of unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, and substituted or unsubstituted silyl;

Ar as described ₁ 、Ar ₂ 、L ₂ 、L ₃ All as claimed in claim 1;

8. The carbazoloindole derivative according to claim 1, wherein the carbazoloindole derivative is selected from one of the following compounds:

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9. An organic electroluminescent device comprising an anode, a cathode and an organic layer comprising at least one of a hole transport region between the anode and the cathode, a light emitting layer, an electron transport region, and a cover layer on a side of the cathode facing away from the anode, wherein the organic layer comprises one or more carbazolo indole derivatives as claimed in any one of claims 1 to 8.

10. The organic electroluminescent device according to claim 9, wherein the organic layer comprises a light-emitting layer, wherein the light-emitting layer contains one or more carbazoloindole derivatives according to any one of claims 1 to 8.