CN116283814A

CN116283814A - Heterocyclic compound and organic electroluminescent device thereof

Info

Publication number: CN116283814A
Application number: CN202211683107.1A
Authority: CN
Inventors: 郭建华; 杜明珠; 周雯庭
Original assignee: Changchun Hyperions Technology Co Ltd
Current assignee: Changchun Hyperions Technology Co Ltd
Priority date: 2022-12-27
Filing date: 2022-12-27
Publication date: 2023-06-23

Abstract

The invention relates to the technical field of organic photoelectric materials, in particular to a heterocyclic compound and an organic electroluminescent device thereof. The invention provides a heterocyclic compound which has a triplet state energy level higher than that of a luminescent substance, proper HOMO and LUMO and good electromigration capacity, can improve the luminous efficiency of a device, reduce the driving voltage of the device and prolong the service life of the device when being used as a main body material or an electron transport material, and is an OLED material with excellent performance.

Description

Heterocyclic compound and organic electroluminescent device thereof

Technical Field

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

Background

An Organic Light-Emitting Diode (OLED) has the characteristics of Light and thin body, wide viewing angle, quick response, 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 light-emitting layer is sandwiched between two electrodes of a cathode and an anode, wherein the light-emitting layer contains a light-emitting substance (guest material), 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 light-emitting layer, excitons are generated by recombination, energy is released, the excitons migrate under the action of an electric field, energy is transferred to the light-emitting substance, electrons in molecules of the light-emitting substance migrate from a ground state to an excited state, and then migrate from an unstable excited state to a stable ground state, and in the process, the energy is released in a light form, thereby generating a light-emitting phenomenon. 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 in general, a hole transmission area is arranged between the anode and the light-emitting layer to perform the functions of injecting and transmitting holes and the like, and the hole transmission area 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 has the functions of injecting and transmitting electrons and the like, and comprises an electron injection layer, an electron transmission layer, a hole blocking layer and the like.

In general, the light-emitting layer includes a host material in addition to the light-emitting substance, which mainly plays a role in transferring energy to the light-emitting substance, and this requires that T1 (triplet energy level) of the host material must be higher than T1 of the light-emitting substance, and generally requires more than 2.75eV, so that it can be ensured that the energy between the host material and the light-emitting substance is an exothermic process, and there is no possibility that the light-emitting substance transfers energy back to the host material. In addition, the highest occupied orbital level (HOMO) and the lowest unoccupied orbital Level (LUMO) of the host material need to be matched with other adjacent organic functional layers in the device to facilitate injection of holes and electrons, and the singlet energy level of the molecule needs to be relatively close to the triplet energy level, so that the driving voltage is reduced. The host material molecules also need to have good carrier transport properties so that holes and electrons can recombine well. Other organic functional layers generally need to have proper energy level matching and carrier transport capabilities, for example, each organic functional layer in an electron transport region needs to have good energy level matching with an adjacent organic functional layer, and also needs to have good electron transport capabilities, and the like.

In order to further improve the driving voltage, luminous efficiency, color purity, service life, and other properties of the OLED device, development of a host material, an electron transport material, and the like having more excellent properties is still required.

Disclosure of Invention

In order to solve the technical problems, the invention provides a heterocyclic compound which has proper three-wire energy level, HOMO and LUMO, has good carrier transmission capability, also has good thermal stability and chemical stability, can be used as a main material or an electron transmission material to be applied to an OLED device, further effectively improves the luminous efficiency, the driving voltage, the service life and other performances of the OLED device, and has one of structures shown in formulas (I-A) - (I-C):

wherein, X is ₁ Selected from oxygen, sulfur or NR ₁ Said R is ₁ Each occurrence of which is identically or differently 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 substituted or unsubstituted C2-C30 heteroaryl group;

said X ₂ Selected from oxygen atoms or sulfur atoms;

the A is selected from one of structures shown in formulas (A-1) to (A-10):

In the formulae (A-1) to (A-2), the Y ₁ ～Y ₆ Independently selected from CR ₂ Or nitrogen atoms, and up to 4 are selected from the group consisting of nitrogen atoms, said Y ₁ ～Y ₆ Is linked to L and is selected from carbon atoms; in the formulae (A-3) to (A-8), the Y ₁ ～Y ₈ Independently selected from CR ₂ Or nitrogen atoms, and up to 4 are selected from the group consisting of nitrogen atoms, said Y ₁ 、Y ₂ 、Y ₅ ～Y ₈ Is linked to L and is selected from carbon atoms; in the formulae (A-9) to (A-10), the Y ₁ ～Y ₁₀ Independently selected from CR ₂ Or nitrogen atoms, and up to 4 are selected from the group consisting of nitrogen atoms, said Y ₁ ～Y ₁₀ Is linked to L and is selected from carbon atoms; said R is ₂ Each occurrence of which is the same or different and is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 and a substituted or unsubstituted C2-C30 heteroaryl group;

ar as described ₁ One selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl group;

ar as described ₂ One selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, and a substituted or unsubstituted C2-C30 heteroaryl group;

L is selected from one of substituted or unsubstituted C6-C30 arylene and substituted or unsubstituted C2-C30 heteroarylene; the substituent in the "substituted or unsubstituted" is selected from one or more of the following: deuterium atoms; cyano group; a halogen atom; C1-C10 alkyl substituted or unsubstituted by one or more of deuterium atom, cyano group and halogen atom; a C6-C12 aryl group substituted or unsubstituted with one or more of deuterium atom, cyano group, halogen atom, C1-C4 alkyl group; C2-C10 heteroaryl substituted or unsubstituted by one or more of deuterium atom, cyano group, halogen atom and C1-C4 alkyl group;

said X ₃ Selected from CR ₃ Or a nitrogen atom, said R ₃ One selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, and a substituted or unsubstituted C2-C30 heteroaryl group;

the B is selected from one of structures shown in formulas (B-1) to (B-11):

in formula (B-1), said Z ₁ ～Z ₄ Independently selected from CR ₄ Or nitrogen atoms, and up to 3 selected from nitrogen atoms, in formula (I-C), said Z ₁ ～Z ₄ Is linked to L and is selected from carbon atoms; in the formulae (B-2) to (B-2)In the formula (B-3), the Z ₁ ～Z ₆ Independently selected from CR ₄ Or nitrogen atoms, and up to 4 are selected from nitrogen atoms, in formula (I-C), said Z ₃ ～Z ₆ Is linked to L and is selected from carbon atoms; in the formulae (B-4) to (B-9), the Z ₁ ～Z ₈ Independently selected from CR ₄ Or nitrogen atoms, and up to 4 are selected from nitrogen atoms, in formula (I-C), said Z ₃ ～Z ₈ Is linked to L and is selected from carbon atoms; in the formulae (B-10) to (B-11), the Z ₁ ～Z ₁₀ Independently selected from CR ₄ Or nitrogen atoms, and up to 4 are selected from nitrogen atoms, in formula (I-C), said Z ₃ ～Z ₁₀ Is linked to L and is selected from carbon atoms; said R is ₄ And is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, and a substituted or unsubstituted C2-C30 heteroaryl group.

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 heterocyclic compound.

The beneficial effects are that:

the heterocyclic compounds shown in the formulas (I-A) - (I-C) have a triplet state energy level higher than that of a luminescent material, and are beneficial to the energy transfer of the host material to the luminescent material when being used as the host material in an OLED device, and the phenomenon that the energy is transferred back to the host material from the guest material does not occur, and the heterocyclic compounds also have proper HOMO and LUMO, can be well matched with adjacent organic functional layers, effectively reduce energy loss, further improve the luminous efficiency of the device, reduce the driving voltage of the device and prolong the service life of the device; the heterocyclic compound also has good electron migration capability, and when being used as a main material or an electron transport material, the heterocyclic compound is matched with a proper hole transport material or other main materials, so that the electron transport efficiency can be improved, the recombination of electrons and holes in a light-emitting layer is facilitated, and the light-emitting efficiency of the device is further improved; the heterocyclic compound has good thermal stability and chemical stability, and can delay the aging of the device under the working environment of high temperature and corrosive gas, thereby further prolonging the service life of the device.

In conclusion, the heterocyclic compound provided by the invention is an OLED material with excellent performance.

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.

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

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 cyclopentenyl group, a cyclohexenyl group, a cyclopentenyl 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.

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.

"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 heterocyclic group, substituted or unsubstituted C1-C30 alkoxy group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C6-C60 aryloxy group, substituted or unsubstituted C2-C60 heteroaryl group, 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 heterocyclic group, C6-C30 aryl group, C3-C30 heteroaryl group, silyl group, in the case of being substituted with a plurality of substituents, the plurality of substituents are 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, chlorine atom, bromine atom, iodine atom, cyano group, nitro 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, n-propyl group, sec-butyl group, tert-butyl group, deuterated tert-butyl group, cyclopropane group, methyl-substituted cyclobutane group ethyl substituted cyclobutyl, deuterated cyclobutyl, cyclopentyl, methyl substituted cyclopentyl, ethyl substituted cyclopentyl, deuterated cyclopentyl, cyclohexenyl, methyl substituted cyclohexenyl, ethyl substituted cyclohexenyl, n-propyl substituted cyclohexenyl, n-butyl substituted cyclohexenyl, cyclohexane substituted cyclohexenyl, deuterated cyclohexenyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cyclohexenyl, and the like methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazinyl, ethyl-substituted piperazinyl, phenyl-substituted piperazinyl, naphthyl-substituted piperazinyl, methoxy, ethoxy, phenyl, deuterophenyl, naphthyl, deuterated naphthyl, anthracenyl, deuterated anthracenyl, phenanthrenyl, deuterated phenanthrenyl, triphenylenyl, pyrenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, 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 an aromatic ring is not fixed, it means that it can be attached to any of the optional sites of the aromatic ring. For example, the number of the cells to be processed,

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->

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:

the present invention provides a heterocyclic compound having one of structures represented by formulas (I-A) to (I-C):

wherein, X is ₁ Selected from oxygen, sulfur or NR ₁ Said R is ₁ Each occurrence of which is the same or different and is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 and a substituted or unsubstituted C2-C30 heteroaryl group;

Said X ₂ Selected from oxygen atoms or sulfur atoms;

said X ₂ Selected from oxygen atoms or sulfur atoms;

the A is selected from one of structures shown in formulas (A-1) to (A-10):

in the formulae (A-1) to (A-2), the Y ₁ ～Y ₆ Independently selected from CR ₂ Or nitrogen atoms, and up to 4 are selected from the group consisting of nitrogen atoms, said Y ₁ ～Y ₆ Is linked to L and is selected from carbon atoms; in the formulae (A-3) to (A-8), the Y ₁ ～Y ₈ Independently selected from CR ₂ Or nitrogen atoms, and up to 4 are selected from the group consisting of nitrogen atoms, said Y ₁ 、Y ₂ 、Y ₅ ～Y ₈ Is linked to L and is selected from carbon atoms; in the formulae (A-9) to (A-10), the Y ₁ ～Y ₁₀ Independently selected from CR ₂ Or alternativelyA nitrogen atom and up to 4 atoms selected from the group consisting of nitrogen atoms, said Y ₁ ～Y ₁₀ Is linked to L and is selected from carbon atoms; said R is ₂ Each occurrence of which is the same or different and is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 and a substituted or unsubstituted C2-C30 heteroaryl group;

the B is selected from one of structures shown in formulas (B-1) to (B-11):

in formula (B-1), said Z ₁ ～Z ₄ Independently selected from CR ₄ Or nitrogen atoms, and up to 3 selected from nitrogen atoms, in formula (I-C), said Z ₁ ～Z ₄ Is linked to L and is selected from carbon atoms; in the formulae (B-2) to (B-3), the Z ₁ ～Z ₆ Independently selected from CR ₄ Or nitrogen atoms, and up to 4 are selected from nitrogen atoms, in formula (I-C), said Z ₃ ～Z ₆ Is linked to L and is selected from carbon atoms; in the formulae (B-4) to (B-9), the Z ₁ ～Z ₈ Independently selected from CR ₄ Or nitrogen atoms, and up to 4 are selected from nitrogen atoms, in formula (I-C), said Z ₃ ～Z ₈ Is linked to L and is selected from carbon atoms; in the formulae (B-10) to (B-11), the Z ₁ ～Z ₁₀ Independently selected from CR ₄ Or nitrogen atoms, and up to 4 are selected from nitrogen atoms, in formula (I-C), said Z ₃ ～Z ₁₀ Is linked to L and is selected from carbon atoms; said R is ₄ And is selected from one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, and a substituted or unsubstituted C2-C30 heteroaryl group.

Preferably, the substituents in said "substituted or unsubstituted" are selected from deuterium atoms; a halogen atom; cyano group; a C1-C12 alkyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a halogen atom, a cyano group, a C1-C4 alkyl group, a C6-C20 aryl group, and a C2-C20 heteroaryl group; a C3-C12 cycloalkyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a halogen atom, a cyano group, a C1-C4 alkyl group, a C6-C20 aryl group, and a C2-C20 heteroaryl group; a C3-C12 cycloalkenyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a halogen atom, a cyano group, a C1-C4 alkyl group, a C6-C20 aryl group, and a C2-C20 heteroaryl group; a heterocycloalkyl group having 3 to 12 ring atoms which is substituted or unsubstituted with one or more of deuterium atom, halogen atom, cyano group, C1 to C4 alkyl group, C6 to C20 aryl group, C2 to C20 heteroaryl group; a C6-C30 aryl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a halogen atom, a cyano group, a C1-C4 alkyl group, a C6-C20 aryl group, and a C2-C20 heteroaryl group; a C3-C30 heteroaryl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a halogen atom, a cyano group, a C1-C4 alkyl group, a C6-C20 aryl group, and a C2-C20 heteroaryl group; one of a silyl group substituted or unsubstituted by one or more than one of the group consisting of a deuterium atom, a halogen atom, a cyano group, a C1-C4 alkyl group, a C6-C20 aryl group, and a C2-C20 heteroaryl group, wherein the heterocycloalkyl group or heteroaryl group contains at least one of O, S, N, si, se, P, and wherein the substituents are one or more, when the substituents are plural, the substituents are the same or different, and when there are plural substituents, adjacent two substituents are optionally linked to form a saturated or unsaturated C3-C10 carbocyclic ring.

Preferably, the substituents in said "substituted or unsubstituted" are selected from deuterium atoms; a fluorine atom; cyano group; a methyl group; trifluoromethyl; deuterated methyl; an ethyl group; deuterated ethyl; n-propyl; an isopropyl group; deuterated isopropyl; n-butyl; sec-butyl; an isobutyl group; a tertiary butyl group; deuterated tert-butyl; a cyclopropane group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a cyclobutyl group substituted or unsubstituted by one or more than one kind selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, t-butyl group, deuterated t-butyl group, phenyl group, deuterated phenyl group, pentafluorophenyl group, naphthyl group, deuterated naphthyl group, biphenyl group and deuterated biphenyl group; a cyclopentylalkyl group substituted or unsubstituted with one or more than one kind selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a cyclohexylalkyl group which is substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a cyclopropenyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a cyclobutenyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a cyclopentenyl group substituted or unsubstituted with one or more than one of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, t-butyl group, deuterated t-butyl group, phenyl group, deuterated phenyl group, pentafluorophenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, deuterated biphenyl group; a cyclohexenyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, t-butyl group, deuterated t-butyl group, phenyl group, deuterated phenyl group, pentafluorophenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, deuterated biphenyl group; an adamantyl group substituted or unsubstituted with one or more than one kind selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, t-butyl group, deuterated t-butyl group, phenyl group, deuterated phenyl group, pentafluorophenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, deuterated biphenyl group; norbornyl substituted or unsubstituted with one or more of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, t-butyl group, deuterated t-butyl group, phenyl group, deuterated phenyl group, pentafluorophenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, deuterated biphenyl group; a tetrahydropyrrole group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a piperidyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; morpholinyl substituted or unsubstituted with one or more of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, t-butyl group, deuterated t-butyl group, phenyl group, deuterated phenyl group, pentafluorophenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, deuterated biphenyl group; a thiomorpholinyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; piperazinyl substituted or unsubstituted with one or more of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, t-butyl group, deuterated t-butyl group, phenyl group, deuterated phenyl group, pentafluorophenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, deuterated biphenyl group; phenyl substituted or unsubstituted with one or more of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, t-butyl group, deuterated t-butyl group, phenyl group, deuterated phenyl group, pentafluorophenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, deuterated biphenyl group; a naphthyl 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 trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; an anthracene group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; phenanthryl substituted or unsubstituted with one or more of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, t-butyl group, deuterated t-butyl group, phenyl group, deuterated phenyl group, pentafluorophenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, deuterated biphenyl group; a triphenylene group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; 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 trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl 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 deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, t-butyl group, deuterated t-butyl group, phenyl group, deuterated phenyl group, pentafluorophenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, deuterated biphenyl group; a spiro-cyclopentyl-fluorenyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a spiro-cyclohexyl-fluorenyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a spiro-adamantyl-fluorenyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuteromethyl group, an ethyl group, an isopropyl group, a deuterohsopropyl group, a t-butyl group, a deuteroht-butyl group, a phenyl group, a deuterohenyl group, a pentafluorophenyl group, a naphthyl group, a deuterohenyl group, a biphenyl group, and a deuterohenyl group; a spiro-cyclopentenyl-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 trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a spiro-cyclohexenyl-fluorenyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a carbazolyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a furan 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 trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; thienyl substituted or unsubstituted with one or more of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, t-butyl group, deuterated t-butyl group, phenyl group, deuterated phenyl group, pentafluorophenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, deuterated biphenyl group; benzofuranyl substituted or unsubstituted with one or more of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, t-butyl group, deuterated t-butyl group, phenyl group, deuterated phenyl group, pentafluorophenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, deuterated biphenyl group; a benzothienyl group substituted or unsubstituted with one or more than one of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, t-butyl group, deuterated t-butyl group, phenyl group, deuterated phenyl group, pentafluorophenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, deuterated biphenyl group; a dibenzofuranyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a dibenzothiophene group substituted or unsubstituted with one or more than one kind selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a pyridyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; pyrimidinyl substituted or unsubstituted with one or more of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, t-butyl group, deuterated t-butyl group, phenyl group, deuterated phenyl group, pentafluorophenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, deuterated biphenyl group; triazinyl substituted or unsubstituted with one or more of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, t-butyl group, deuterated t-butyl group, phenyl group, deuterated phenyl group, pentafluorophenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, deuterated biphenyl group; a pyrazinyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a pyridazinyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; a quinolinyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a pentafluorophenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, and a deuterated biphenyl group; an isoquinolinyl group substituted or unsubstituted with one or more than one of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, t-butyl group, deuterated t-butyl group, phenyl group, deuterated phenyl group, pentafluorophenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, deuterated biphenyl group; a quinoxalinyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuteromethyl group, an ethyl group, an isopropyl group, a deuteroiisopropyl group, a tert-butyl group, a deuteroit-butyl group, a phenyl group, a deuteroiphenyl group, a pentafluorophenyl group, a naphthyl group, a deuteroinaphthyl group, a biphenyl group, and a deuteroibiphenyl group; quinazolinyl substituted or unsubstituted by one or more of the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, trifluoromethyl group, deuterated methyl group, ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, phenyl group, deuterated phenyl group, pentafluorophenyl group, naphthyl group, deuterated naphthyl group, biphenyl group, deuterated biphenyl group; one or more substituted or unsubstituted silyl groups selected from the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuteromethyl, ethyl, isopropyl, deuteromethyl, tert-butyl, deuterated tert-butyl, phenyl, deuterophenyl, pentafluorophenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl, wherein one or more of the substituents are the same or different when a plurality of substituents are present, and adjacent two substituents are optionally linked to form a saturated or unsaturated C3-C10 carbocyclic ring.

Preferably, said R ₁ The substituents are, for each occurrence, the same or different selected from the group consisting of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted t-butyl, substituted or unsubstituted cyclopropanyl, substituted or unsubstituted cyclobutylalkyl, substituted or unsubstituted cyclopentanyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyridazine, substituted or unsubstituted quinolinyl, and unsubstituted quinolinyl.

Preferably, said R ₁ At each occurrence, is selected identically or differently from methyl, deuteromethyl, ethyl, isopropyl, deuterated isopropyl, t-butyl, deuterated t-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthylphenyl, deuterated naphthylphenyl, phenylnaphthyl, deuterated benzeneOne of a naphthylnaphthyl group, a methyl substituted phenyl group, an isopropyl substituted phenyl group, a tert-butyl substituted phenyl group, and an adamantyl substituted phenyl group.

Preferably, in the formulae (A-1) to (A-2), the Y ₁ ～Y ₆ Up to 3 selected from nitrogen atoms, and one of which is linked to L and is selected from carbon atoms; in the formulae (A-3) to (A-8), the Y ₁ ～Y ₈ Up to 3 of said atoms are selected from nitrogen atoms, and said Y ₁ 、Y ₂ 、Y ₅ ～Y ₈ Is linked to L and is selected from carbon atoms; in the formulae (A-9) to (A-10), the Y ₁ ～Y ₁₀ Up to 3 of which are selected from nitrogen atoms and one of which is linked to L and is selected from carbon atoms.

Preferably, in the formulae (A-1) to (A-2), the Y ₁ ～Y ₆ Up to 2 of which are selected from nitrogen atoms and one of which is linked to L and is selected from carbon atoms; in the formulae (A-3) to (A-8), the Y ₁ ～Y ₈ Up to 2 of said atoms are selected from nitrogen atoms, and said Y ₁ 、Y ₂ 、Y ₅ ～Y ₈ Is linked to L and is selected from carbon atoms; in the formulae (A-9) to (A-10), the Y ₁ ～Y ₁₀ Up to 2 of which are selected from nitrogen atoms and one of which is linked to L and is selected from carbon atoms.

Preferably, in the formulae (A-1) to (A-2), the Y ₁ ～Y ₆ Up to 1 selected from nitrogen atoms, and one of which is linked to L and is selected from carbon atoms; in the formulae (A-3) to (A-8), the Y ₁ ～Y ₈ Up to 1 of them is selected from nitrogen atoms, and said Y ₁ 、Y ₂ 、Y ₅ ～Y ₈ Is linked to L and is selected from carbon atoms; in the formulae (A-9) to (A-10), the Y ₁ ～Y ₁₀ Up to 1 selected from nitrogen atoms, and one of which is linked to L, is selected from carbon atoms.

Preferably, a is selected from one of the following structures:

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wherein, a is as follows ₁₁ Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b ₁₁ Each occurrence is identically or differently selected from 0, 1 or 2; the said c ₁₁ Each occurrence is identically or differently selected from 0 or 1; d is as follows ₁₁ Each occurrence is identically or differently selected from 0, 1, 2 or 3;

said R is ₁₁ And is selected from the group consisting of hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuteromethyl group, trifluoromethyl group, ethyl group, deuteroethyl group, n-propyl group, isopropyl group, deuterated isopropyl group, n-butyl group, tert-butyl group, deuterated tert-butyl group, cyclopentyl group, deuterated cyclopentyl group, cyclohexenyl group, deuterated cyclohexenyl group, phenyl group, deuterated phenyl group, pyridyl group, deuterated pyridyl group, pyrimidinyl group, deuterated pyrimidinyl group, triazinyl group, deuterated triazinyl group, pyrazinyl group, deuterated pyrazinyl group, pyridazinyl group, deuterated pyridazinyl group, and the like.

Preferably, said Ar ₁ Selected from a hydrogen atom, a deuterium atom, a cyano group, a halogen atom or one of the structures shown below:

wherein, a is as follows ₂₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; said b ₂₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6 or 7; the said c ₂₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; d is as follows ₂₁ At each occurrence, are identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or

11; said e ₂₁ At each time of occurrence of this, the process is completed,the same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15; said f ₂₁ Each occurrence is identically or differently selected from 0, 1, 2 or 3; g is as described ₂₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said h ₂₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the i is ₂₁ Is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, identically or differently at each occurrence,

13 or 14; said j ₂₁ Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said k ₂₁ Each occurrence is identically or differently selected from 0, 1 or 2; the l is ₂₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6;

said R is ₂₁ Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, deuteromethyl, trifluoromethyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentylalkyl, deuterated cyclopentylalkyl, cyclohexenyl, deuterated cyclohexenyl, adamantyl, norbornyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracenyl, deuterated anthracenyl, phenanthryl, deuterated phenanthryl, triphenylene, deuterated triphenylene, biphenyl, deuterated biphenyl, indanyl, deuterated indanyl, tetrahydronaphthyl, deuterated tetrahydronaphthyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, pyridyl, deuterated pyridyl, pyrimidinyl, deuterated pyrimidinyl, triazinyl, deuterated triazinyl, pyrazinyl, substituted pyrazinyl, pyridazinyl, deuteropyridazinyl, quinolyl, isoquinolyl, quinazolinyl, and monoquinolinyl.

Preferably, said Ar ₁ Selected from a hydrogen atom, a deuterium atom, a cyano group, a fluorine atom or one of the structures shown below:

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wherein, a is as follows ₃₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said b ₃₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the said c ₃₁ The same or different at each occurrence is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15; d is as follows ₃₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6 or 7; said e ₃₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; said f ₃₁ Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; g is as described ₃₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said h ₃₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the i is ₃₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said j ₃₁ Each occurrence is identically or differently selected from 0, 1, 2 or 3; said k ₃₁ And is selected, identically or differently, for each occurrence, from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14.

Preferably, said Ar ₂ Selected from a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, an n-propyl group, an isopropyl group, a deuterated isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a cyano group, a halogen atom or one of the structures shown below:

wherein, a is as follows ₂₁ 、b ₂₁ 、c ₂₁ 、d ₂₁ 、e ₂₁ 、f ₂₁ 、g ₂₁ 、h ₂₁ 、i ₂₁ 、j ₂₁ 、k ₂₁ 、l ₂₁ 、R ₂₁ All as described herein.

Preferably, said Ar ₂ Selected from a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyano group, a fluorine atom or one of the structures shown below:

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wherein, a is as follows ₃₁ 、b ₃₁ 、c ₃₁ 、d ₃₁ 、e ₃₁ 、f ₃₁ 、g ₃₁ 、h ₃₁ 、i ₃₁ 、j ₃₁ 、k ₃₁ All as described herein.

Preferably, L is selected from one of the following structures:

wherein, a is as follows ₄₁ Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b ₄₁ Each occurrence is identically or differently selected from 0, 1, 2 or 3; the said c ₄₁ Each occurrence is identically or differently selected from 0, 1 or 2; d is as follows ₄₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said e ₄₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said f ₄₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; g is as described ₄₁ Each occurrence of which is the same or differentFrom 0 or 1;

said R is ₄₁ And is selected, identically or differently, at each occurrence from one of a hydrogen atom, a deuterium atom, a cyano group, a fluorine atom, a methyl group, a deuteromethyl group, a trifluoromethyl group, an ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentylalkyl group, a deuterated cyclopentylalkyl group, a cyclohexenyl group, an adamantyl group, a norbornyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, a biphenyl group, a deuterated biphenyl group, a pyridyl group, a deuterated pyridyl group, a pyrimidinyl group, a deuterated pyrimidinyl group, a triazinyl group, a deuterated triazinyl group, a pyrazinyl group, a deuterated pyrazinyl group, a pyridazinyl group, a deuterated pyridazinyl group, a quinolinyl group, a deuterated quinolinyl group, an isoquinolinyl group, a deuterated quinoxalinyl group, a quinazolinyl group, and a deuterated quinazolinyl group.

Preferably, L is selected from one of the following structures:

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wherein, a is as follows ₅₁ Each occurrence is identically or differently selected from 1, 2, 3 or 4; said b ₅₁ Each occurrence is identically or differently selected from 1, 2 or 3; the said c ₅₁ Each occurrence is identically or differently selected from 1 or 2; d is as follows ₅₁ Each occurrence is identically or differently selected from 1, 2, 3, 4, 5 or 6; said e ₅₁ Each occurrence is identically or differently selected from 1, 2, 3, 4 or 5; said f ₅₁ Each occurrence is identically or differently selected from 1, 2, 3, 4, 5, 6, 7 or 8; g is as described ₅₁ Each occurrence is identically or differently selected from 1, 2, 3, 4, 5, 6 or 7;

said R is ₅₁ One selected from hydrogen atom, deuterium atom, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl and deuterated biphenyl.

Preferably, the B is selected from one of the following structures:

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wherein,,

represented by the formulae (I-A) and (I-B), and represented by the formula (I-C) is a bond to L; the a ₁₁ 、b ₁₁ 、c ₁₁ 、d ₁₁ 、R ₁₁ All as described herein.

Preferably, the heterocyclic compound is selected from one of the following structures:

wherein, the A, B, ar ₁ 、Ar ₂ 、R ₁ 、R ₃ And L are as described in the invention. Preferably, the heterocyclic compound is selected from one of the following structures:

wherein, the A, B, ar ₁ 、Ar ₂ 、R ₁ And L are as described in the invention.

wherein the saidA, B, ar of (5) ₁ 、Ar ₂ 、R ₁ 、R ₃ And L are as described in the invention. Most preferably, the heterocyclic compound is selected from one of the following compounds:

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The above only shows some specific structural forms of the heterocyclic compounds represented by the formulae (I-A) to (I-C), but the present invention is not limited to these chemical structures, and substituents are included as defined in the present invention even when the heterocyclic compounds are represented by the formulae (I-A) to (I-C).

The heterocyclic compounds represented by the formulas (I-A) to (I-C) can be prepared by one of the following synthetic routes:

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wherein x is selected from

Y is selected from chlorine atom, bromine atom or iodine atom;

a, B, X described in ₁ 、X ₂ 、X ₃ 、Ar ₁ 、Ar ₂ And L are as described in the invention.

In each of the above synthetic routes, the target compounds (I-A) to (I-C) can be obtained by Suzuki coupling reaction of the compound Y (i.e., the compounds Y-A to Y-L) with the compound Z (i.e., the compounds Z-A to Z-D).

The above reaction schemes are all of the types of reactions commonly used in organic synthesis, and the reaction conditions (e.g., selection and amounts of the reaction solvents, catalysts, ligands, bases, etc., and the order and method of addition) are not particularly limited. The preparation method has the advantages of easily available raw materials, simple preparation process and excellent yield. The compounds represented by the formulas (I-A) to (I-C) provided by the invention can be synthesized by adopting the conventional reaction types in other organic synthesis, and the compounds are not particularly limited, and the above are only examples of synthetic routes.

Preferably, the organic layer includes a hole transport region, a light emitting layer and an electron transport region between the anode and the cathode, at least one of the light emitting layer and the electron transport region contains one or more heterocyclic compounds of the present invention; further preferably, the light-emitting layer contains one or more heterocyclic compounds of the present invention.

Preferably, the organic layer comprises a hole transport region, a light emitting layer, an electron transport region and a cover layer on one side of the cathode away from the anode, wherein at least one of the light emitting layer, the electron transport region and the cover layer contains more than one heterocyclic compound; further preferably, the light-emitting layer or the electron-transporting region contains one or more heterocyclic compounds of the present invention; still more preferably, the light-emitting layer contains one or more heterocyclic compounds 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.

Preferably, the hole transport region includes at least two layers of a hole injection layer, a hole transport layer, and a light emitting auxiliary layer; further preferably, the hole transport region includes a hole injection layer and a hole transport layer.

Preferably, the hole transport region includes 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-Carbazolyl) Biphenyl (CBP), 4' -tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (2-naphthyl) Anthracene (ADN), the heterocyclic compound described in the present invention, but is not limited thereto. Preferably, the host material contains more than one heterocyclic compound.

Preferably, the host material contains at least two different compounds, and at least one selected from the heterocyclic compounds of the present invention. Further preferably, the host material contains two different compounds, the heterocyclic compound of the present invention is used as an n-type host, and the other compound is used as a p-type host. The p-type host may be 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 the like, and carbazole derivatives are preferably used, and specific examples thereof include, but are not limited to, compounds H-1 to H-17 shown below. Still more preferably, the mass ratio of the heterocyclic compound (n-type host) to the p-type host used in combination is 1: 10-10: 1. Most preferably, the mass ratio of the heterocyclic compound (n-type main body) to the p-type main body used in a matching way is 1: 5-5: 1.

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.

Preferably, the electron transport region includes at least two layers of an electron injection layer, an electron transport layer and a hole blocking layer; further preferably, the electron transport region includes an electron injection layer and an electron transport layer.

Preferably, the electron transport region includes 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 are not limited toThis is done.

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), the heterocyclic compounds described in the present invention, and the like, but are 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 complex, lithium complex, beryllium complex, oxazole derivative, benzoxazole derivative, thiazole derivative, benzothiazole derivative, imidazole derivative, benzimidazole derivative, phenanthroline derivative, polymer compound, and the like. Examples thereof include, but are not limited to, 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBI), BAlq, heterocyclic compounds of the present invention, and the like. Preferably, the hole blocking layer contains the heterocyclic compound of the present invention.

The anode of the invention can be a reflecting anode, such as a reflecting 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) and 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 The heterocyclic compounds according to the invention include, but are not limited to, compound CP-1, compound CP-2, compound CP-3, compound CP-4.

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 6

Preparation of intermediate bb-6:

aa-6 (23.76 g,120.00 mmol), pinacol diboronate (33.52 g,132.00 mmol), CH were added to the flask under nitrogen ₃ COOK(15.31g，156.00mmol)、Pd(dppf)Cl ₂ (0.44 g,0.60 mmol) and 900ml THF were reacted under reflux for 7 hours. After the reaction, cooling to room temperature, adding water, suction-filtering to obtain a filter cake, drying in a vacuum oven, and separating and purifying the crude product by a silica gel column (n-hexane: ethyl acetate=1:1) to obtain an intermediate bb-6 (24.12 g, yield 82%); HPLC purity is more than or equal to 99.78%. Mass spectrum m/z:245.1235 (theory: 245.1223).

Preparation of intermediate dd-6:

into a reaction flask was charged bb-6 (19.61 g,80.00 mmol), cc-6 (28.72 g,80.00 mmol), under nitrogen,Na ₂ CO ₃ (12.72g,120.00mmol)、Pd(PPh ₃ ) ₄ (0.92 g,0.80 mmol) and 320ml of 1, 4-dioxane were reacted under reflux for 8.5 hours. After the reaction was completed, the mixture was cooled to room temperature, water was then added thereto, the mixture was extracted with methylene chloride, and the organic layer was dried over anhydrous MgSO ₄ Drying, removal of solvent under reduced pressure, recrystallisation from toluene/petroleum ether=4:1 gives intermediate dd-6 (21.29 g, 76% yield); HPLC purity is more than or equal to 99.70%. Mass spectrum m/z:349.0120 (theory: 349.0102).

Preparation of intermediate ee-6:

into a reaction flask was charged dd-6 (17.51 g,50.00 mmol), pinacol diboronate (13.97 g,55.00 mmol), K under nitrogen ₂ CO ₃ (8.98g，65.00mmol)、Pd(dppf)Cl ₂ (0.18 g,0.25 mmol) and 435ml THF were reacted under reflux for 6.5 hours. After the reaction was completed, cooled to room temperature, water was added, and suction filtration was performed to obtain a cake, which was recrystallized from toluene/n-hexane=5:1 to obtain intermediate ee-6 (15.49 g, yield 78%); HPLC purity is more than or equal to 99.80%. Mass spectrum m/z:397.1840 (theory: 397.1849).

Preparation of Compound 6:

under the protection of nitrogen, ee-6 (11.92 g,30.00 mmol), ff-6 (9.89 g,30.00 mmol) and Na were added to the flask ₂ CO ₃ (4.77g，45.00mmol)、Pd(OAc) ₂ (0.07g，0.30mmol)、P(t-Bu) ₃ (0.06 g,0.30 mmol) and 120ml THF, and reacted under reflux for 8 hours. After the completion of the reaction, the mixture was cooled to room temperature, water was then added thereto, the mixture was extracted with chloroform, and the organic layer was dried over anhydrous MgSO ₄ Drying, removal of solvent under reduced pressure, and recrystallization from toluene gave compound 6 (12.54 g, yield 74%); HPLC purity is more than or equal to 99.92%. Mass spectrum m/z:564.1827 (theory: 564.1838). Theoretical element content (%) C ₄₀ H ₂₄ N ₂ O ₂ : c,85.09; h,4.28; n,4.96. Measured element content (%): c,85.06; h,4.24; n,4.99.

Synthesis example 2: synthesis of Compound 51

According to the same manner as that of Synthesis example 1 except that dd-6 and ff-6 were replaced with equimolar dd-51 and ff-51, compound 51 (11.51 g, yield 76%) was obtained, and the purity of the solid was found to be not less than 99.94% by HPLC. Mass spectrum m/z:504.1283 (theory: 504.1296). Theoretical element content (%) C ₃₄ H ₂₀ N ₂ OS: c,80.93; h,4.00; n,5.55. Measured element content (%): c,80.97; h,4.03; n,5.52. Synthesis example 3: synthesis of Compound 57

According to the same manner as that of Synthesis example 1 except that cc-6 and ff-6 were replaced with equimolar cc-57 and ff-57, compound 57 (12.56 g, yield: 72%) was obtained, and the purity of the solid was not less than 99.90% by HPLC. Mass spectrum m/z:581.1573 (theory: 581.1562). Theoretical element content (%) C ₃₉ H ₂₃ N ₃ OS: c,80.53; h,3.99; n,7.22. Measured element content (%): c,80.50; h,3.95; n,7.26. Synthesis example 4: synthesis of Compound 118

According to the same manner as that of Synthesis example 1 except that dd-6 and ff-6 were replaced with equimolar dd-118 and ff-118, compound 118 (12.89 g, yield: 74%) was obtained, and the purity of the solid was found to be not less than 99.97% by HPLC. Mass spectrum m/z:580.1621 (theory: 580.1609). Theoretical element content (%) C ₄₀ H ₂₄ N ₂ OS: c,82.73; h,4.17; n,4.82. Measured element content (%): c,82.76; h,4.12; n,4.86.

Synthesis example 5: synthesis of Compound 142

According to the synthesis ofExample 1 the same procedure was followed except that aa-6, cc-6, ff-6 were replaced with equimolar aa-142, cc-142, ff-142 to give compound 142 (11.60 g, 73% yield) with a purity of 99.91% solids as determined by HPLC. Mass spectrum m/z:529.1642 (theory: 529.1633). Theoretical element content (%) C ₃₄ H ₁₁ D ₉ N ₂ S ₂ : c,77.09; h,5.52; n,5.29. Measured element content (%): c,77.13; h,5.49; n,5.33.

Synthesis example 6: synthesis of Compound 290

According to the same manner as that of Synthesis example 1, aa-6, cc-6 and ff-6 were replaced with aa-290, aa-6 and ff-290 in equimolar amounts, respectively, to give compound 290 (11.14 g, yield: 72%) and a solid purity of not less than 99.91% by HPLC. Mass spectrum m/z:515.1622 (theory: 515.1634). Theoretical element content (%) C ₃₅ H ₂₁ N ₃ O ₂ : c,81.54; h,4.11; n,8.15. Measured element content (%): c,81.51; h,4.16; n,8.18.

Synthesis example 7: synthesis of Compound 292

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-290, aa-6 and ff-292 in equimolar amounts, compound 292 (12.70 g, yield: 75%) was obtained, and the purity of the solid was not less than 99.96% by HPLC detection. Mass spectrum m/z:564.1825 (theory: 564.1838). Theoretical element content (%) C ₄₀ H ₂₄ N ₂ O ₂ : c,85.09; h,4.28; n,4.96. Measured element content (%): c,85.12; h,4.23; n,4.93.

Synthesis example 8: synthesis of Compound 293

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-293, cc-142 and ff-6 in equimolar amounts, compound 293 (12.37 g, yield: 71%) was obtained, and the purity of the solid was not less than 99.96% by HPLC detection. Mass spectrum m/z:580.1623 (theory: 580.1609). Theoretical element content (%) C ₄₀ H ₂₄ N ₂ OS: c,82.73; h,4.17; n,4.82. Measured element content (%): c,82.70; h,4.13; n,4.86.

Synthesis example 9: synthesis of Compound 316

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with dd-118, cc-316 and ff-316 in equimolar amounts, compound 316 (12.87 g, yield 68%) was obtained, and the purity of the solid was not less than 99.92% by HPLC detection. Mass spectrum m/z:630.1526 (theory: 630.1514). Theoretical element content (%) C ₄₂ H ₂₂ N ₄ OS: c,79.98; h,3.52; n,8.88. Measured element content (%): c,79.93; h,3.55; n,8.84.

Synthesis example 10: synthesis of Compound 325

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-290, cc-325 and ff-292 in equimolar amounts, compound 325 (12.51 g, yield 74%) was obtained, and the purity of the solid was not less than 99.93% by HPLC. Mass spectrum m/z:563.1876 (theory: 563.1885). Theoretical element content (%) C ₄₁ H ₂₅ NO ₂ : c,87.37; h,4.47; n,2.49. Measured element content (%): c,87.33; h,4.44; n,2.52.

Synthesis example 11: synthesis of Compound 339

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-339, cc-339 and ff-339 in equimolar amounts, compound 339 (13.12 g, yield: 70%) was obtained, and the purity of the solid was not less than 99.94% by HPLC detection. Mass spectrum m/z:624.1431 (theory: 624.1442). Theoretical element content (%) C ₄₀ H ₂₄ N ₄ S ₂ : c,76.90; h,3.87; n,8.97. Measured element content (%): c,76.94; h,3.84; n,8.95.

Synthesis example 12: synthesis of Compound 353

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-142, cc-353 and ff-353 in equimolar amounts, compound 353 (15.08 g, yield: 73%) was obtained, and the purity of the solid was not less than 99.96% by HPLC. Mass spectrum m/z:668.2420 (theory: 668.2402). Theoretical element content (%) C ₄₈ H ₂₄ D ₄ N ₂ O ₂ : c,86.20; h,4.82; n,4.19. Measured element content (%): c,86.23; h,4.86; n,4.14.

Synthesis example 13: synthesis of Compound 356

According to the same manner as that of Synthesis example 1, aa-6, cc-6 and ff-6 were replaced with aa-339, aa-6 and ff-356 in equimolar amounts, respectively, to give 356 (12.75 g, yield: 75%) as compound, and the purity of the solid was not less than 99.91% by HPLC. Mass spectrum m/z:564.1849 (theory: 564.1838). Theoretical element content (%) C ₄₀ H ₂₄ N ₂ O ₂ : c,85.09; h,4.28; n,4.96. Measured element content (%): c,85.05; h,4.31; n,4.98.

Synthesis example 14: synthesis of Compound 366

According to the same manner as that of Synthesis example 1, aa-6, cc-6 and ff-6 were replaced with aa-293, aa-6 and ff-366 in equimolar amounts, respectively, to obtain compound 366 (17.15 g, yield: 71%) having a solid purity of 99.95% or more as measured by HPLC. Mass spectrum m/z:804.2790 (theory: 804.2777). Theoretical element content (%) C ₅₉ H ₃₆ N ₂ O ₂ : c,88.04; h,4.51; n,3.48. Measured element content (%): c,88.08; h,4.54; n,3.44.

Synthesis example 15: synthesis of Compound 379

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-293, cc-379 and ff-379 in equimolar amounts, compound 379 (14.51 g, yield: 72%) was obtained, and the purity of the solid was not less than 99.96% by HPLC. Mass spectrum m/z:671.1729 (theory: 671.1741). Theoretical element content (%) C ₄₇ H ₂₉ NS ₂ : c,84.02; h,4.35; n,2.08. Measured element content (%): c,84.06; h,4.38; n,2.03.

Synthesis example 16: synthesis of Compound 401

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-401, aa-339 and ff-401 in equimolar amounts, compound 401 (12.62 g, yield: 74%) was obtained, and the purity of the solid was not less than 99.93% by HPLC detection. Mass spectrum m/z:568.2073 (theory: 568.2089). Theoretical element content (%) C ₄₀ H ₂₀ D ₄ N ₂ O ₂ : c,84.49; h,4.96; n,4.93. Measured element content (%): c,84.52; h,4.92; n,4.97.

Synthesis example 17: synthesis of Compound 432

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-432, aa-6 and ff-353 in equimolar amounts, compound 432 (12.70 g, yield: 75%) was obtained, and the purity of the solid was not less than 99.92% by HPLC detection. Mass spectrum m/z:564.1850 (theory: 564.1838). Theoretical element content (%) C ₄₀ H ₂₄ N ₂ O ₂ : c,85.09; h,4.28; n,4.96. Measured element content (%): c,85.04; h,4.25; n,4.92.

Synthesis example 18: synthesis of Compound 441

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-142, cc-441 and ff-441 in equimolar amounts, compound 441 (13.90 g, yield: 73%) was obtained, and the purity of the solid was not less than 99.92% by HPLC. Mass spectrum m/z:634.2032 (theory: 634.2017). Theoretical element content (%) C ₄₄ H ₂₂ D ₄ N ₂ OS: c,83.25; h,4.76; n,4.41. Measured element content (%): c,83.21; h,4.73; n,4.45.

Synthesis example 19: synthesis of Compound 449

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According to the same manner as that of Synthesis example 1, aa-6, cc-6 and ff-6 were replaced with aa-449, aa-6 and ff-449 in equimolar amounts, respectively, to give compound 449 (13.42 g, yield 68%) and a solid purity of not less than 99.97% by HPLC. Mass spectrum m/z:657.2203 (theory: 657.2216). Theoretical element content (%) C ₄₆ H ₂₈ FN ₃ O：C,84.00；H4.29; n,6.39. Measured element content (%): c,84.03; h,4.26; n,6.34.

Synthesis example 20: synthesis of Compound 476

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-339, cc-476 and ff-57 in equimolar amounts, compound 476 (14.38 g, yield 73%) was obtained, and the purity of the solid was not less than 99.96% by HPLC. Mass spectrum m/z:656.1906 (theory: 656.1922). Theoretical element content (%) C ₄₆ H ₂₈ N ₂ OS: c,84.12; h,4.30; n,4.27. Measured element content (%): c,84.08; h,4.27; n,4.31.

Synthesis example 21: synthesis of Compound 488

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-488, cc-488 and ff-488 in equimolar amounts, compound 488 (14.51 g, yield: 70%) was obtained and the purity of the solid was not less than 99.92% by HPLC. Mass spectrum m/z:690.2572 (theory: 690.2581). Theoretical element content (%) C ₄₈ H ₂₂ D ₈ N ₂ OS: c,83.45; h,5.54; n,4.05. Measured element content (%): c,83.48; h,5.58; n,4.01.

Synthesis example 22: synthesis of Compound 506

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-506, cc-506 and ff-449 in equimolar amounts, compound 506 (14.41 g, 67% yield) was obtained, and the purity of the solid was not less than 99.93% by HPLC. Mass spectrum m/z:716.2590 (theory: 716.2576). Theoretical element content(％)C ₅₁ H ₃₂ N ₄ O: c,85.45; h,4.50; n,7.82. Measured element content (%): c,85.49; h,4.53; n,7.85.

Synthesis example 23: synthesis of Compound 518

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-401, cc-518 and ff-292 in equimolar amounts, compound 518 (13.93 g, yield: 72%) was obtained, and the purity of the solid was not less than 99.96% by HPLC detection. Mass spectrum m/z:644.2416 (theory: 644.2402). Theoretical element content (%) C ₄₆ H ₂₄ D ₄ N ₂ O ₂ : c,85.69; h,5.00; n,4.34. Measured element content (%): c,85.64; h,5.03; n,4.38.

Synthesis example 24: synthesis of Compound 605

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-605, cc-605 and ff-6 in equimolar amounts, compound 605 (14.01 g, yield: 73%) was obtained, and the purity of the solid was not less than 99.92% by HPLC detection. Mass spectrum m/z:639.1932 (theory: 639.1947). Theoretical element content (%) C ₄₅ H ₂₅ N ₃ O ₂ : c,84.49; h,3.94; n,6.57. Measured element content (%): c,84.45; h,3.91; n,6.53.

Synthesis example 25: synthesis of Compound 615

According to the same manner as that of Synthesis example 1 except that dd-6 and ff-6 were replaced with equimolar dd-615 and ff-615, respectively, compound 615 (12.20 g, yield 67%) was obtained, and the purity of the solid was found to be greater than or equal to 99.95% by HPLC. Mass spectrum m/z:606.2316 (theory: 606.2307). Theoretical element content (%) C ₄₃ H ₃₀ N ₂ O ₂ : c,85.12; h,4.98; n,4.62. Measured element content (%): c,85.16; h,4.95; n,4.67.

Synthesis example 26: synthesis of Compound 633

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-633, cc-633 and ff-6 in equimolar amounts, compound 633 (14.90 g, yield: 72%) was obtained, and the purity of the solid was not less than 99.91% as measured by HPLC. Mass spectrum m/z:689.2369 (theory: 689.2355). Theoretical element content (%) C ₅₁ H ₃₁ NO ₂ : c,88.80; h,4.53; n,2.03. Measured element content (%): c,88.85; h,4.50; n,2.07.

Synthesis example 27: synthesis of Compound 685

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with equimolar amounts of cc-142, cc-685 and ff-57, compound 685 (12.67 g, yield: 74%) was obtained, and the purity of the solid was not less than 99.93% by HPLC. Mass spectrum m/z:570.1216 (theory: 570.1224). Theoretical element content (%) C ₃₈ H ₂₂ N ₂ S ₂ : c,79.97; h,3.89; n,4.91. Measured element content (%): c,79.93; h,3.85; n,4.95.

Synthesis example 28: synthesis of Compound 748

According to the same production method as that of Synthesis example 1, aa-6, cc-6 and ff-6 were replaced with aa-748, cc-441 and ff-748 in equimolar amounts, respectively, to obtainCompound 748 (13.56 g, yield 70%) was found to be at least 99.94% pure by HPLC. Mass spectrum m/z:645.1862 (theory: 645.1875). Theoretical element content (%) C ₄₄ H ₂₇ N ₃ OS: c,81.84; h,4.21; n,6.51. Measured element content (%): c,81.80; h,4.24; n,6.53.

Synthesis example 29: synthesis of Compound 749

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-749, cc-749 and ff-749 in equimolar amounts, compound 749 (15.13 g, yield: 68%) was obtained, and the purity of the solid was not less than 99.93% by HPLC. Mass spectrum m/z:741.2406 (theory: 741.2416). Theoretical element content (%) C ₅₃ H ₃₁ N ₃ O ₂ : c,85.81; h,4.21; n,5.66. Measured element content (%): c,85.85; h,4.17; n,5.69.

Synthesis example 30: synthesis of Compound 752

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-752, aa-6 and ff-353 in equimolar amounts, compound 752 (12.71 g, yield: 71%) was obtained, and the purity of the solid was not less than 99.96% by HPLC detection. Mass spectrum m/z:596.2351 (theory: 596.2340). Theoretical element content (%) C ₄₂ H ₁₆ D ₈ N ₂ O ₂ : c,84.54; h,5.40; n,4.69. Measured element content (%): c,84.57; h,5.44; n,4.64.

Synthesis example 31: synthesis of Compound 769

The same preparation as in Synthesis example 1Aa-6, cc-6 and ff-6 were replaced with equimolar aa-769, cc-769 and ff-769, respectively, to give compound 769 (12.72 g, 67% yield), and the purity of the solid was not less than 99.92% by HPLC. Mass spectrum m/z:632.1683 (theory: 632.1671). Theoretical element content (%) C ₄₂ H ₂₄ N ₄ OS: c,79.73; h,3.82; n,8.85. Measured element content (%): c,79.78; h,3.85; n,8.81.

Synthesis example 32: synthesis of Compound 790

According to the same manner as that of Synthesis example 1 except that dd-6 and ff-6 were replaced with equimolar dd-790 and ff-476, compound 790 (12.52 g, yield 69%) was obtained, and the purity of the solid was found to be 99.95% or more by HPLC. Mass spectrum m/z:604.1625 (theory: 604.1609). Theoretical element content (%) C ₄₂ H ₂₄ N ₂ OS: c,83.42; h,4.00; n,4.63. Measured element content (%): c,83.46; h,4.03; n,4.59.

Synthesis example 33: synthesis of Compound 866

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-866, cc-142 and ff-292 in equimolar amounts, compound 866 (13.74 g, yield: 75%) was obtained, and the purity of the solid was not less than 99.93% by HPLC detection. Mass spectrum m/z:610.1159 (theory: 610.1174). Theoretical element content (%) C ₄₀ H ₂₂ N ₂ OS ₂ : c,78.66; h,3.63; n,4.59. Measured element content (%): c,78.62; h,3.66; n,4.54.

Synthesis example 34: synthesis of Compound 868

According to the same manner as that of Synthesis example 1 except that dd-6 was replaced with equimolar dd-868, compound 868 (13.95 g, yield 71%) was obtained, and the purity of the solid as measured by HPLC was not less than 99.95%. Mass spectrum m/z:654.2320 (theory: 654.2307). Theoretical element content (%) C ₄₇ H ₃₀ N ₂ O ₂ : c,86.22; h,4.62; n,4.28. Measured element content (%): c,86.26; h,4.65; n,4.23.

Synthesis example 35: synthesis of Compound 896

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with equimolar amounts of cc-142, cc-896 and ff-292, compound 896 (12.00 g, yield: 72%) was obtained, and the purity of the solid was not less than 99.95% by HPLC. Mass spectrum m/z:555.1415 (theory: 555.1405). Theoretical element content (%) C ₃₇ H ₂₁ N ₃ OS: c,79.98; h,3.81; n,7.56. Measured element content (%): c,79.93; h,3.85; n,7.53.

Synthesis example 36: synthesis of Compound 897

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with equimolar amounts of ff-292, cc-897 and ff-897, compound 897 (13.10 g, yield: 69%) was obtained, and the purity of the solid was not less than 99.91% by HPLC. Mass spectrum m/z:632.1660 (theory: 632.1671). Theoretical element content (%) C ₄₂ H ₂₄ N ₄ OS: c,79.73; h,3.82; n,8.85. Measured element content (%): c,79.70; h,3.85; n,8.81.

Synthesis example 37: synthesis of Compound 898

The same preparation method as in Synthesis example 1 was followed except that cc-6 and ff-6 were replaced with equimolar cc-898 and ff-57, respectively, to give compound 898 (12.74 g, yield 73%) having a solid purity of 99.93% or higher as measured by HPLC. Mass spectrum m/z:581.1578 (theory: 581.1562). Theoretical element content (%) C ₃₉ H ₂₃ N ₃ OS: c,80.53; h,3.99; n,7.22. Measured element content (%): c,80.57; h,3.96; n,7.25.

Synthesis example 38: synthesis of Compound 899

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-899, cc-142 and ff-292 in equimolar amounts, compound 899 (12.72 g, yield: 70%) was obtained, and the purity of the solid was not less than 99.94% by HPLC detection. Mass spectrum m/z:605.1576 (theory: 605.1562). Theoretical element content (%) C ₄₁ H ₂₃ N ₃ OS: c,81.30; h,3.83; n,6.94. Measured element content (%): c,81.26; h,3.86; n,6.97.

Synthesis example 39: synthesis of Compound 900

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-900, cc-900 and cc-142 in equimolar amounts, compound 900 (12.89 g, yield 69%) was obtained, and the purity of the solid was not less than 99.92% as measured by HPLC. Mass spectrum m/z:622.1273 (theory: 622.1286). Theoretical element content (%) C ₄₀ H ₂₂ N ₄ S ₂ : c,77.15; h,3.56; n,9.00. Measured element content (%): c,77.11; h,3.53; n,9.03.

Synthesis example 40: synthesis of Compound 901

According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-901, cc-379 and ff-6 in equimolar amounts, compound 901 (14.33 g, yield 65%) was obtained, and the purity of the solid was not less than 99.97% by HPLC detection. Mass spectrum m/z:734.2155 (theory: 734.2140). Theoretical element content (%) C ₅₀ H ₃₀ N ₄ OS: c,81.72; h,4.11; n,7.62. Measured element content (%): c,81.68; h,4.14; n,7.66.

Synthesis example 41: synthesis of Compound 902

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According to the same manner as that of Synthesis example 1 except that aa-6, cc-6 and ff-6 were replaced with aa-902, cc-142 and ff-292 in equimolar amounts, compound 902 (11.71 g, yield: 67%) was obtained, and the purity of the solid as determined by HPLC was not less than 99.92%. Mass spectrum m/z:582.1528 (theory: 582.1514). Theoretical element content (%) C ₃₈ H ₂₂ N ₄ OS: c,78.33; h,3.81; n,9.62. Measured element content (%): c,78.30; h,3.85; n,9.66.

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 heterocyclic compounds described in the present invention:

test software, computer, K2400 digital Source Table from Keithley, USA, and PR78 from Photo Research, USA8 spectrum scanning brightness meter forms a combined IVL test system, and the device prepared by the invention is tested under the atmospheric pressure and room temperature under the 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 M6000OLED lifetime test system at atmospheric pressure and room temperature. The test results are shown in tables 1 to 3. 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. 2-TNATA is used as a hole injection layer with the thickness of 60nm; b. NPB is used as a hole transport layer, and the thickness is 40nm; c. HOST-1 and Ir (dpm) (piq) ₂ (mass ratio 96:4) as a light-emitting layer, the thickness was 35nm; d. NBphen and Liq (mass ratio 5:4) are used as electron transport layers with the thickness of 35nm; e. LiF is used as an electron injection layer, and the thickness is 0.2nm; f. mg and Ag (mass ratio 7:1) are used as cathodes with the thickness of 10nm; g: CP-4 was used as a coating layer with a thickness of 100nm.

Comparative device preparation example 2: contrast device 2

The comparative device 2 was obtained by replacing HOST-1 in the light-emitting layer with HOST-2 and performing the same procedure as in comparative device preparation example 1. Device preparation examples 1 to 41: light emitting devices 1 to 41

The HOST-1 in the light-emitting layer was replaced with the heterocyclic compound of the present invention in synthesis examples 1 to 41, respectively, and the other steps were the same as those of comparative device preparation example 1, to obtain light-emitting devices 1 to 41.

TABLE 1

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Comparative device preparation example 3: contrast device 3

The following layers are evaporated layer by layer on the ITO/Ag/ITO glass substrate: a. hat is used as a hole injection layer, and the thickness is 5nm; b. HT-9 is used as a hole transport layer, and the thickness is 40nm; c. HOST-1, H-4 and Ir (ppy) ₂ (m-bppy) (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 35nm; e. NBphen and Liq (mass ratio 3:1) are used as electron transport layers with the thickness of 25nm; f. LiF is used as an electron injection layer, and the thickness is 0.2nm; g. mg and Ag (mass ratio 1:3) 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 example 4: contrast device 4

The comparative device 4 was obtained by replacing HOST-1 in the light-emitting layer with HOST-2 and the other steps were the same as those of comparative device preparation 3. Device preparation examples 42 to 82: light emitting devices 42 to 82

The light-emitting devices 42 to 82 were obtained by replacing HOST-1 in the light-emitting layer with the heterocyclic compounds of the present invention in Synthesis examples 1 to 41, respectively, and the other steps were the same as those of comparative device preparation example 3.

TABLE 2

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Comparative device preparation example 5: contrast device 5

The following layers are evaporated layer by layer on the ITO/Ag/ITO glass substrate: a. HT-3 and p-1 (mass ratio 100:3) as hole injection layers with thickness of 25nm; b. HT-3 is used as a hole transport layer, and the thickness is 35nm; c. NPB is used as a light-emitting auxiliary layer, and the thickness is 30nm; d. BH and BD (mass ratio 97:3) as light-emitting layers, thickness 35nm; d. HOST-1 is used as a hole blocking layer, and the thickness is 30nm; e. NBphen and Liq (mass ratio 3:1) are used as electron transport layers with the thickness of 25nm; f. LiF is used as an electron injection layer, and the thickness is 0.2nm; g. mg and Ag (mass ratio 5:1) 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 6 to 7: contrast devices 6 to 7

HOST-1 in the hole blocking layer was replaced with HOST-2 and HB-1, respectively, and the other steps were the same as those of comparative device preparation example 5, thereby obtaining comparative devices 6 to 7.

Device preparation examples 83 to 123: light emitting devices 83 to 123

The hole-blocking layer HOST-1 was replaced with the heterocyclic compound of the present invention in Synthesis examples 1 to 41, respectively, and the other steps were the same as those of comparative device preparation example 5, thereby obtaining light-emitting devices 83 to 123.

TABLE 3 Table 3

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The device data in tables 1-3 show that when the heterocyclic compound provided by the invention is used as a main material of a luminescent layer and a hole blocking layer, the driving voltage, the luminous efficiency and the service life of the device are all obviously improved, and the heterocyclic compound provided by the invention is an OLED material with excellent performance and has a good application prospect.

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 heterocyclic compound characterized by having one of structures represented by formulas (I-a) to (I-C):

said X ₂ Selected from oxygen atoms or sulfur atoms;

the A is selected from one of structures shown in formulas (A-1) to (A-10):

Said X ₃ Selected from CR ₃ Or a nitrogen atom, said R ₃ Selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstitutedCycloalkyl of C3-C10, aryl of substituted or unsubstituted C6-C30, heteroaryl of substituted or unsubstituted C2-C30;

the B is selected from one of structures shown in formulas (B-1) to (B-11):

2. The heterocyclic compound according to claim 1, wherein R ₁ The groups are selected, identically or differently, for each occurrence, from substituted or unsubstituted methyl groups, substituted or unsubstituted ethyl groups, substituted or unsubstituted n-propyl groups, takenSubstituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or 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 benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinyl, or an unsubstituted quinazoline.

3. The heterocyclic compound of claim 1, wherein a is selected from one of the structures shown below:

4. The heterocyclic compound according to claim 1, wherein Ar is ₁ Selected from a hydrogen atom, a deuterium atom, a cyano group, a halogen atom or one of the structures shown below:

Ar as described ₂ Selected from a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, an n-propyl group, an isopropyl group, a deuterated isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a cyano group, a halogen atom or one of the structures shown below:

wherein, a is as follows ₂₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; said b ₂₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6 or 7; the said c ₂₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; d is as follows ₂₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said e ₂₁ The same or different at each occurrence is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15; by a means ofF is described in ₂₁ Each occurrence is identically or differently selected from 0, 1, 2 or 3; g is as described ₂₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said h ₂₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the i is ₂₁ The same or different at each occurrence is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; said j ₂₁ Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said k ₂₁ Each occurrence is identically or differently selected from 0, 1 or 2; the l is ₂₁ Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6;

5. The heterocyclic compound of claim 1, wherein L is selected from one of the structures shown below:

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

6. The heterocyclic compound of claim 1, wherein B is selected from one of the structures shown below:

wherein,,

represented by the formulae (I-A) and (I-B), and represented by the formula (I-C) is a bond to L;

the a ₁₁ 、b ₁₁ 、c ₁₁ 、d ₁₁ 、R ₁₁ A method as claimed in claim 3.

7. The heterocyclic compound according to claim 1, wherein the heterocyclic compound is selected from one of the following structures:

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8. 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, characterized in that the organic layer contains one or more heterocyclic compounds according to claims 1 to 7.

9. The organic electroluminescent device according to claim 8, wherein the organic layer comprises a hole transport region, a light emitting layer and an electron transport region between the anode and the cathode, wherein at least one of the light emitting layer and the electron transport region contains one or more heterocyclic compounds according to claims 1 to 7.

10. The organic electroluminescent device according to claim 8, wherein the organic layer comprises 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 at least one of the light emitting layer, the electron transport region, and the cover layer contains one or more heterocyclic compounds according to claims 1 to 7.