CN113880854A - Organic compound containing spiro furocarbazole structure and application thereof - Google Patents

Organic compound containing spiro furocarbazole structure and application thereof Download PDF

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CN113880854A
CN113880854A CN202111159864.4A CN202111159864A CN113880854A CN 113880854 A CN113880854 A CN 113880854A CN 202111159864 A CN202111159864 A CN 202111159864A CN 113880854 A CN113880854 A CN 113880854A
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substituted
unsubstituted
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aromatic hydrocarbon
hydrocarbon group
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向陆军
张小玲
曹占广
杭德余
陈婷
程丹丹
班全志
段陆萌
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Beijing Yunji Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons

Abstract

The invention relates to the technical field of organic electroluminescent display, and particularly discloses an organic compound containing a spiro furocarbazole structure, and also discloses an application of the organic compound in an organic electroluminescent device. The organic compound containing the spiro furocarbazole structure has the structure shown in the general formula (I), can be applied to the field of organic electroluminescence, and particularly can be used as a hole transport material for a hole transport layer of an organic electroluminescent device. The organic compound with the structure provided by the invention is applied to an OLED device, can reduce the driving voltage and improve the luminous efficiency of the device.

Description

Organic compound containing spiro furocarbazole structure and application thereof
Technical Field
The invention relates to the technical field of materials for organic electroluminescent display, and particularly discloses an organic compound containing a spiro furocarbazole structure, and also discloses an application of the organic compound in an organic electroluminescent device.
Background
Organic electroluminescent diodes (OLEDs) are also known as organic electroluminescent displays, organic light emitting semiconductors. Originally discovered in 1979 by professor dung Qing cloud in the laboratory, there has been a development course of more than 40 years to date. Since the OLED has a series of advantages of self-luminescence, lightness, thinness, power saving, high contrast, wide viewing angle, high response speed, rich colors and the like, the OLED is often used in the fields of display and illumination, is expected to replace the existing liquid crystal display and fluorescent illumination in the future, has a very wide application prospect, and also attracts the attention of a plurality of researchers. In order to improve the light emitting efficiency and extend the service life of the light emitting device, the development and research of the light emitting device are increasingly active.
Materials used to make OLEDs generally include electrode materials, light emitting materials, and auxiliary materials. Wherein the auxiliary material mainly comprises a carrier transport material, a carrier injection material and a carrier blocking material. Different assist materials play different roles in the device and therefore often have different performance requirements for the different assist materials.
Taking hole transport materials as an example, the hole transport materials are mainly used for transporting holes, improving the transport efficiency of the holes in the device, blocking electrons in the light emitting layer and realizing the maximum recombination of carriers. Therefore, hole transport materials for OLEDs generally have to meet the following performance requirements:
(1) has high hole mobility;
(2) the triplet state energy level of the molecule is higher than the excitation energy of the light-emitting layer;
(3) the film has good film forming property, and can form a uniform and amorphous thin film without defects;
(4) the melting point and the glass transition temperature are higher;
(5) the appropriate HOMO energy level can ensure the effective injection and transmission of holes between various interfaces.
At present, more and more display manufacturers are invested in research and development, and the industrialization process of the OLED is greatly promoted. However, the conventional organic electroluminescent materials still have room for improvement in light-emitting properties, and development of new organic electroluminescent materials is urgently needed in the art.
The invention aims to provide a stable and efficient hole transport material to reduce the driving voltage and improve the luminous efficiency of a device, which has important practical application value.
Disclosure of Invention
The invention aims to provide a stable and efficient organic hole transport material which is applied to an OLED device, can reduce the driving voltage and improve the luminous efficiency of the device.
Specifically, in a first aspect, the present invention provides an organic compound containing a spiro furocarbazole structure, having a structure represented by general formula (i):
Figure BDA0003289634670000021
wherein:
R1～R3each independently represents H, halogen, substituted or unsubstituted C1～C20A chain alkyl group of (A), a substituted or unsubstituted C3～C20Cycloalkyl, substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a);
R1～R3the groups represented by each may be the same or different; r1～R3At least one of them represents substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a);
m, n and p are each independently selected from integers of 1 to 4; preferably, m, n and p are each independently selected from 1 or 2; more preferably, m, n and p are all 1;
R4、R5each independently represents H, halogen, amino, substituted or unsubstituted C1～C20A chain alkyl group of (A), a substituted or unsubstituted C3～C20Cycloalkyl, substituted or unsubstituted C3～C60Arylamine or heteroarylamine, substituted or unsubstituted C3～C60Aryl or heteroaryl of (a); r4、R5The groups represented by each may be the same or different;
q and r are each independently selected from integers of 1 to 4; preferably, q, r are each independently selected from 1 or 2; more preferably, q and r are both 1;
R1～R5when a substituent exists on the group represented by (A), the substituents are respectively and independently selected from C1～C20Chain alkyl group of (2), C3～C20A cycloalkane group of6～C30Aryl group of (1).
As a preferred embodiment of the present invention, in the general formula (I), said substituted or unsubstituted C6～C40In the monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), the monocyclic aromatic hydrocarbon group is an aromatic hydrocarbon group containing one benzene ring; and/or the polycyclic aromatic hydrocarbon group is a polyphenyl aliphatic hydrocarbon group, biphenyl and biphenyl polycyclic aromatic hydrocarbon group, spirobifluorene group or fused ring aromatic hydrocarbon group.
Preferably, said substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a) is optionally selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted benzo (a) anthracenyl group, a substituted or unsubstituted benzo (b) phenanthrenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted fluorenyl group, or a substituted phenanthrenyl group, or a substituted or unsubstituted fluorenyl group, or a substituted fluorenyl group, or a substituted phenanthrenyl group, or a substituted or unsubstituted fluorenyl group, a substituted or a substituted fluorenyl group, a substituted or a substituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or a substituted or unsubstituted fluorenyl group, a substituted or a substituted or a substituted or a substituted or unsubstituted phenanthrenyl group, or substituted or a substituted or a substituted or substitutedSubstituted benzo (b) fluoranthenyl, substituted or unsubstituted benzo (k) fluoranthenyl, substituted or unsubstituted benzo (a) pyrenyl, substituted or unsubstituted indenofluoranthenyl, substituted or unsubstituted perylenyl;
when the substituent exists, the number of the substituent is 1-3, and the substituent is respectively and independently selected from C1～C20Chain alkyl group of (2), C3～C20A cycloalkane group of1～C10Alkoxy group of (C)1～C10Thioalkoxy of, C6～C30Arylamino group of (C)3～C30Heteroarylamino of (A), C6～C30Aryl of (C)3～C30The heteroaryl group of (a).
As a further preferred embodiment of the present invention, in the general formula (I), said substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a) is optionally selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted indenopluoranthenyl group, a substituted or unsubstituted perylenyl group;
the substituted substituent can be 1-2, and the substituent is selected from C1～C5Chain alkyl group of (1), C3～C6Cycloalkyl, phenyl, biphenyl, naphthyl, phenanthryl, anthracyl, benzo, triphenylene, naphtho, fluoranthenyl.
More preferably, in the general formula (I), said substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group is optionally selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl groupSubstituted or unsubstituted fluoranthenyl, substituted or unsubstituted perylene;
when substituents are present, the substituents are each independently selected from C1～C5Chain alkyl group of (1), C3～C6The number of the substituents is selected from an integer of 1 to 2.
Wherein, C1～C5The chain alkyl group of (a) includes, but is not limited to: methyl, ethyl, propyl (n-propyl, isopropyl), butyl, etc.; c3～C6Cycloalkyl groups of (a) include, but are not limited to: cyclopropyl, cyclopentyl, cyclohexyl, and the like.
As a preferred embodiment of the present invention, R in the formula (I)5Is H, in particular a structure represented by the general formula (II):
Figure BDA0003289634670000041
in the formula (II), R is1、R2、R3、R4M, n, p, q are as defined in formula (I).
Preferably, in formula (II), m, n, p and q are each independently selected from 1 or 2; more preferably, m, n, p and q are all 1.
As a preferred embodiment of the present invention, R in the formula (II)4Is H, in particular a structure represented by the general formula (III):
Figure BDA0003289634670000042
in the formula (III), the R1、R2、R3M, n and p are as defined for formula (I).
Preferably, in formula (III), m, n and p are each independently selected from 1 or 2; more preferably, m, n and p are all 1.
In the formula (III), the R1、R2、R3May be the same or different.
As a preferred embodiment of the present invention, in the general formula (I), the general formula (II) or the general formula (III), R is1～R3Each independently represents H, phenyl, substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a); and said R is1～R3At least one of them represents substituted or unsubstituted C6～C40Monocyclic aromatic hydrocarbon group or polycyclic aromatic hydrocarbon group of (a).
Preferably, said substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a) is optionally selected from any one of the following groups:
Figure BDA0003289634670000043
Figure BDA0003289634670000051
the dotted line in the above group represents the position of the access bond of the group.
As a further preferred embodiment, in the general formula (I), (II) or (III), said m, n and p are each 1.
As a further preferred embodiment, in the general formula (I), (II) or (III), said R1、R2、R3Any one of which is said substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a); other groups are H or phenyl.
Or, R1、R2、R3Any two groups in the above list are said substituted or unsubstituted C6～C40The monocyclic or polycyclic aromatic hydrocarbon group of (a), the other groups being H or phenyl; the two groups may be the same or different from each other.
As a still further preferred embodiment, in the general formula (I), (II) or (III), said R1、R2Any one of the groups isThe substituted or unsubstituted C6～C40The monocyclic or polycyclic aromatic hydrocarbon group of (a), the other group being H; r3Is H or phenyl.
Or, R1、R2Is said substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), the two groups being the same as or different from each other; r3Is H or phenyl.
In the present specification, the "substituted or unsubstituted" group may have one substituent or a plurality of substituents, and when a plurality of substituents are present, different substituents may be selected, and when the same expression manner is involved in the present invention, the same meaning is given, and the selection ranges of the substituents are as shown above, and are not described again.
In the present specification, Ca～CbThe expression (a) represents that the group has carbon atoms of a to b unless otherwise specified. Each group in the present specification has a substituent, and the carbon number thereof does not include the carbon number of the substituent.
In the present specification, "independently" means that the subject may be the same or different when a plurality of subjects are provided.
In the present specification, the expression of chemical elements includes the concept of chemically identical isotopes, for example, hydrogen (H) includes1H (protium or H),2H (deuterium or D), etc.; carbon (C) then comprises12C、13C and the like.
In the present specification, the hetero atom in the heteroaryl group generally means an atom or an atomic group selected from N, O, S, P, Si and Se, and preferably N, O or S atom.
In the present specification, the halogen atom is F, Cl, Br or I.
In the present specification, the substituted or unsubstituted chain alkyl group includes a straight-chain alkyl group and an alkyl group having a branched chain. Straight chain alkyl refers to the general formula CnH2n+1Straight chain alkyl of (E) -including but not limited to methyl, ethyl, propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and the like. Preferably, n is a linear alkyl group of 1-5. ComprisesBranched alkyl groups include, but are not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, and the like. The preferred branched alkyl group has 1 to 5 carbon atoms.
In the present specification, cycloalkyl includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and the like. Cycloalkyl groups having 3 to 6 carbon atoms are preferable.
In the present specification, said C6～C40The monocyclic aromatic hydrocarbon group or the monocyclic aromatic hydrocarbon group in the polycyclic aromatic hydrocarbon groups of (1), preferably an aromatic hydrocarbon group containing one benzene ring; the polycyclic aromatic hydrocarbon group is polyphenyl aliphatic hydrocarbon group, biphenyl and biphenyl type polycyclic aromatic hydrocarbon group, spirobifluorene group or condensed ring aromatic hydrocarbon group.
In the present specification, said C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group in the polycyclic aromatic hydrocarbon group of (a) is any one of a polyphenyl aliphatic hydrocarbon group, a biphenyl type polycyclic aromatic hydrocarbon group, a spirobifluorene group and a fused ring aromatic hydrocarbon group, including but not limited to: biphenyl, phenanthryl, fluorenyl, anthracyl, fluoranthenyl, triphenylenyl, naphthyl, and the like. The polycyclic arylo group may be phenanthro, anthraco, fluorantheno, triphenylo, naphtho, or the like.
In the present specification, monocyclic aryl is preferably phenyl; monocyclic aryl-and-heteroaryl are preferably benzo; the heterocyclic aryl is a group with aromatic heterocyclic ring, and can be benzothienyl, benzofuranyl, pyridyl, pyrimidyl, thiazolyl and the like; the heterocycloaryl group may be benzothieno, benzofuro, or the like.
As a preferred embodiment of the present invention, the compound is selected from the group consisting of compounds represented by the following structural formulae:
Figure BDA0003289634670000071
Figure BDA0003289634670000081
Figure BDA0003289634670000091
Figure BDA0003289634670000101
Figure BDA0003289634670000111
in a second aspect, the invention provides an application of the organic compound containing the spiro furocarbazole structure.
In particular, the application is use as a functional material in organic electronic devices including organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information labels, electronic artificial skin sheets, sheet type scanners or electronic paper.
Further, the invention provides application of the organic compound in an organic electroluminescent device.
Preferably, the organic compounds of the present invention are used as hole transport materials in Hole Transport Layers (HTLs) in organic electroluminescent devices.
In a third aspect, the present invention provides an organic electroluminescent device comprising an anode, a cathode and one or more light-emitting functional layers interposed between the anode and the cathode, the light-emitting functional layers containing the organic compound according to the present invention.
Further preferably, the light-emitting functional layer includes at least one of an electron blocking layer, a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, wherein the hole transport layer contains the organic compound according to the present invention.
More preferably, the organic electroluminescent device comprises a transparent substrate, an anode layer, a hole transport layer containing the organic compound of the present invention, an electroluminescent layer, an electron transport layer, an electron injection layer and a cathode layer in sequence from bottom to top.
In a fourth aspect, the present invention provides an organic electronic device wherein the functional material comprises an organic compound according to the present invention. The organic electronic device comprises an organic electroluminescent device, an optical sensor, a solar cell, an illuminating element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet type scanner and electronic paper.
The organic compound shown in the general formula (I) has a mother nucleus structure which adopts a rigid structural unit, and the mother structure has good thermal stability and simultaneously has proper HOMO and LUMO energy levels and Eg; by introducing neutral groups, in particular R, at active sites in the parent nucleus structure1～R3The hole transport performance of the material can be further improved by changing the mode of intermolecular stacking. The organic compound shown in the general formula (I) has higher triplet state energy level, better carrier transmission capability, proper HOMO/LUMO energy level, higher thermal stability and film forming stability. Experiments show that the compounds can be applied to the field of organic electroluminescence, can effectively improve the photoelectric property of an OLED device after being applied to the OLED device as an organic electroluminescence material and used as a hole transport material, and the device has the advantages of low driving voltage and high luminous efficiency, namely the effects of reducing the driving voltage and improving the luminous efficiency can be achieved. The OLED device prepared by the compound can be applied to the field of display or illumination.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention, and it should be understood by those skilled in the art that they are merely examples to assist understanding of the invention and should not be construed as specifically limiting the invention.
According to the method for synthesizing the compound and the method for manufacturing the organic electroluminescent device provided by the present invention, a person skilled in the art can use known common means to realize the method, and the present invention is not particularly limited thereto. If not specifically stated, the starting materials for the preparation of solvents, catalysts, bases, etc. may be obtained by published commercial routes or by methods known in the art.
The synthesis of the compounds of the present invention is briefly described below. The compounds of the general formula (I) of the present invention can be synthesized by a known organic synthesis method. An exemplary synthetic route is given below, and the synthesis of the compounds of formula (I) according to the invention can be accomplished according to the following synthetic methods of intermediates M1-M7. The method can also be obtained by other known methods, such as further selecting suitable catalyst and solvent, and determining suitable reaction temperature, time, material ratio, etc.
Synthesis of intermediates M1-M7
Synthesis of intermediate M1
Figure BDA0003289634670000131
The synthetic route is as follows:
Figure BDA0003289634670000132
the specific operation steps are as follows:
(1) adding 200ml of dichloromethane and 44g M1-01 into a dry 500ml three-necked bottle under the protection of nitrogen, starting stirring, slowly dropwise adding 11ml of liquid bromine at room temperature, dropwise adding for 30min, continuing to react for 2 hours at room temperature after dropwise adding, separating an organic phase after the reaction is finished, extracting, drying, carrying out column chromatography, and spin-drying a solvent to obtain 37.2g of a compound M1-02 with the yield of 62%.
(2) Adding 200ml of anhydrous tetrahydrofuran, 31.4g of 2-chloro-2' -iodobiphenyl into a dry 1L three-necked bottle under the protection of nitrogen, cooling the liquid nitrogen to below-78 ℃, slowly dropwise adding 48ml of n-butyllithium (2.5mol/L), stirring for 1h, slowly dropwise adding an anhydrous tetrahydrofuran solution containing 30g M1-02 into the three-necked bottle under the protection of nitrogen, naturally heating to room temperature, stirring for 10h, and quenching the reaction by using a saturated sodium bicarbonate solution. Separating organic phase, extracting, drying, column chromatography and spin drying solvent to obtain 27.2g of product M1-03 with yield of 56%.
(3) 250ml of toluene and 40g M1-03 and 2.0g of p-toluenesulfonic acid are respectively added into a 500ml three-neck flask with mechanical stirring, stirring is started, heating is carried out until reflux is achieved, and reflux water-diversion reaction is carried out for 6 hours. After the reaction is finished, an organic phase is separated, extracted, dried, subjected to column chromatography and solvent rotary drying to obtain 32.7g of a product M1-04 with the yield of 85%.
(4) Under the protection of nitrogen, 250mL of toluene, 32.7g M1-04, 14.3g N-phenyl-2-chloroaniline, 9.6g of sodium tert-butoxide, 0.64g of dibenzylidene acetone dipalladium and 0.2mL of tri-tert-butylphosphine are respectively added into a 500mL three-necked bottle, magnetic stirring is carried out, heating is carried out until reflux, heat preservation reaction is carried out for 8 hours, after the reaction is finished, an organic phase is separated, extraction, drying, column chromatography and solvent spin drying are carried out, 29.4g of a compound M1-05 are obtained, and the yield is 71%.
(5) Under the protection of nitrogen, 300ml of dimethylformamide, 29.4g M1-05, 13.8g of potassium carbonate and 0.12g of palladium acetate are respectively added into a 500ml three-necked bottle provided with a condenser tube, a magneton and a thermometer, stirring is started, heating is carried out until reflux is achieved, heat preservation reaction is carried out for 4 hours, and the reaction is finished. The organic phase was separated, extracted, dried, column chromatographed and the solvent dried to give 18.1g of intermediate M1 in 65% yield.
Analysis of product M1: MS (m/e): 556.06, respectively; elemental analysis (C)39H22ClNO): theoretical value C: 84.24%, H: 3.99%, N: 2.52 percent; found value C: 84.30%, H: 3.92%, N: 2.48 percent.
Synthesis of intermediate M2
Figure BDA0003289634670000141
Referring to the synthesis method of the intermediate M1, 2-bromo-6-chlorobiphenyl is used for replacing 2-chloro-2' -iodobiphenyl, a proper material ratio is selected, and other raw materials and steps are the same as those of the synthesis method of the intermediate M1, so that the intermediate M2 is obtained.
Analysis of product M2: MS (m/e): 556.06, respectively; elemental analysis (C)39H22ClNO): theoretical value C: 84.24%, H: 3.99%, N: 2.52 percent; found value C: 84.20%, H: 3.96%, N: 2.49 percent.
Synthesis of intermediate M3
Figure BDA0003289634670000142
Referring to the synthesis method of the intermediate M1, 2-bromo-5-chlorobiphenyl is used for replacing 2-chloro-2' -iodobiphenyl, a proper material ratio is selected, and other raw materials and steps are the same as those of the synthesis method of the intermediate M1, so that the intermediate M3 is obtained.
Analysis of product M3: MS (m/e): 556.06, respectively; elemental analysis (C)39H22ClNO): theoretical value C: 84.24%, H: 3.99%, N: 2.52 percent; found value C: 84.3%, H: 3.92%, N: 2.47 percent.
Synthesis of intermediate M4
Figure BDA0003289634670000151
Referring to the synthesis method of the intermediate M1, 2-bromo-4-chlorobiphenyl is used for replacing 2-chloro-2' -iodobiphenyl, a proper material ratio is selected, and other raw materials and steps are the same as those of the synthesis method of the intermediate M1, so that the intermediate M4 is obtained.
Analysis of product M4: MS (m/e): 556.06, respectively; elemental analysis (C)39H22ClNO): theoretical value C: 84.24%, H: 3.99%, N: 2.52 percent; found value C: 84.28%, H: 3.96%, N: 2.49 percent.
Synthesis of intermediate M5
Figure BDA0003289634670000152
Referring to the synthesis method of the intermediate M4, N-biphenyl-2-chloroaniline is used for replacing N-phenyl-2-chloroaniline, a proper material ratio is selected, and other raw materials and steps are the same as those of the synthesis method of the intermediate M4, so that the intermediate M5 is obtained.
Analysis of product M5: MS (m/e): 632.16, respectively; elemental analysis (C)45H26ClNO): theoretical value C: 85.5%, H: 4.15%, N: 2.22 percent; found value C: 85.53%, H: 4.14%, N: 2.20 percent.
Synthesis of intermediate M6
Figure BDA0003289634670000153
Referring to the synthesis method of the intermediate M1, 2-bromo-2 ', 4-dichlorobiphenyl is used for replacing 2-chloro-2' -iodobiphenyl, a proper material ratio is selected, and other raw materials and steps are the same as those of the synthesis method of the intermediate M1, so that the intermediate M6 is obtained.
Analysis of product M6: MS (m/e): 590.5; elemental analysis (C)39H21Cl2NO): theoretical value C: 79.33%, H: 3.58%, N: 2.37 percent; found value C: 79.20%, H: 3.61%, N: 2.42 percent.
Synthesis of intermediate M7
Figure BDA0003289634670000161
Referring to the synthesis method of the intermediate M1, 2 '-dibromo-4-chlorobiphenyl is used for replacing 2-chloro-2' -iodobiphenyl, a proper material ratio is selected, and other raw materials and steps are the same as those of the synthesis method of the intermediate M1, so that the intermediate M7 is obtained.
Analysis of product M7: MS (m/e): 633.95, respectively; elemental analysis (C)39H21BrClNO): theoretical value C: 73.77%, H: 3.33%, N: 2.21 percent; found value C: 73.70%, H: 3.28%, N: 2.26 percent.
The following are examples of synthesis of specific compounds provided by the present invention.
EXAMPLE 1 Synthesis of Compound I-1
Figure BDA0003289634670000162
The synthetic route is as follows:
Figure BDA0003289634670000163
the synthesis of the compound I-1 comprises the following specific steps:
250ml of dioxane were added to a 500ml three-necked flask equipped with a condenser, thermometer and magneton under nitrogen protection, followed by the addition of intermediate M1(27.8g, 0.05mol), pinacol phenylboronate (10g, 0.05mol), cesium carbonate (39g, 0.12mol), tri-tert-butylphosphine (1.2g, 6mmol) and tris (dibenzylideneacetone) dipalladium (0.92, 1.0mmol) in that order. After the addition, heating to reflux reaction for 6 hours, and cooling after the reaction is finished. The reaction solution was adjusted to neutral, and the organic phase was separated, extracted, dried, column chromatographed, and the solvent was spin-dried to give 24.2g of compound I-1 as a pale yellow solid with a yield of about 81.2%.
Product MS (m/e): 597.72, respectively; elemental analysis (C)45H27NO): theoretical value C: 90.43%, H: 4.55%, N: 2.34 percent; found value C: 90.35%, H: 4.60%, N: 2.36 percent.
EXAMPLE 2 Synthesis of Compound I-3
Figure BDA0003289634670000171
The synthetic route is as follows:
Figure BDA0003289634670000172
the synthesis of the compound I-3 comprises the following specific steps:
100ml of toluene, 50ml of ethanol, 50ml of water, followed by intermediate M2(27.8g, 0.05mol), 2-naphthalene boronic acid (8.6g, 0.05mol), sodium bicarbonate (6.3g,0.075mol), 0.1g of Pd132 were added in this order to a 500ml three-necked flask equipped with a condenser, thermometer and magneton under nitrogen. After the addition, heating to reflux reaction for 6 hours, and cooling after the reaction is finished. The reaction solution was adjusted to neutral, and the organic phase was separated, extracted, dried, column chromatographed, and the solvent was dried by spinning to give 23.4g of compound I-3 as a pale yellow solid with a yield of about 72.5%.
Product MS (m/e): 647.78, respectively; elemental analysis (C)49H29NO): theoretical value C: 90.86%, H: 4.51%, N: 2.16 percent; found value C: 90.91%, H: 4.52%, N: 2.11 percent.
EXAMPLE 3 Synthesis of Compound I-18
Figure BDA0003289634670000173
The synthetic route is as follows:
Figure BDA0003289634670000174
the synthesis of the compound I-18 comprises the following specific steps:
intermediate M3 was used in place of intermediate M1, and intermediate M1, 10- (1-naphthyl) -9-anthraceneboronic acid pinacol ester was used in place of phenylboronic acid pinacol ester, and the other raw materials and procedures were the same as in example 1, to obtain 25.2g of compound I-18 as a pale yellow solid with a yield of about 61.2%.
Product MS (m/e): 824.0; elemental analysis (C)63H37NO): theoretical value C: 91.83%, H: 4.53%, N: 1.70 percent; found value C: 91.90%, H: 4.48%, N: 1.69 percent.
EXAMPLE 4 Synthesis of Compound I-20
Figure BDA0003289634670000181
The synthetic route is as follows:
Figure BDA0003289634670000182
the synthesis of the compound I-20 comprises the following specific steps:
intermediate M4 was used in place of M2, triphenylene-2-boronic acid was used in place of 2-naphthaleneboronic acid, the appropriate material ratios were chosen, and the other raw materials and procedures were the same as in example 2, to give 21.8g of compound I-20 as a pale yellow solid with a yield of about 58.5%.
Product MS (m/e): 747.90, respectively; elemental analysis (C)57H33NO): theoretical value C: 91.54%, H: 4.45%, N: 1.87 percent; found value C: 91.58%, H: 4.42%, N: 1.85 percent.
EXAMPLE 5 Synthesis of Compound I-41
Figure BDA0003289634670000183
The synthetic route is as follows:
Figure BDA0003289634670000191
the synthesis of the compound I-41 comprises the following specific steps:
the intermediate M5 was used in place of M1, 2- (9-9-dimethyl-9-fluoren-2-yl) -4,4,5, 5-tetramethyl-1, 3-dioxaborane in place of pinacol ester phenylboronic acid, and the appropriate material ratios were selected, and the other raw materials and procedures were the same as in example 1, whereby 30.0g of the compound I-41 was obtained as a pale yellow solid with a yield of about 65.7%.
Product MS (m/e): 789.98, respectively; elemental analysis (C)60H39NO): theoretical value C: 91.23%, H: 4.98%, N: 1.77 percent; found value C: 91.22%, H: 4.96%, N: 1.80 percent.
EXAMPLE 6 Synthesis of Compound I-47
Figure BDA0003289634670000192
The synthetic route is as follows:
Figure BDA0003289634670000193
the synthesis of the compound I-47 comprises the following specific steps:
intermediate M5 was used in place of M2, 9, 10-bis (2-naphthyl) anthracene-2-boronic acid in place of 2-naphthaleneboronic acid, and the appropriate ratios of materials were selected, and the other raw materials and procedures were the same as in example 2, to give 31.8g of compound I-47 as a pale yellow solid with a yield of about 62.1%.
Product MS (m/e): 1026.25, respectively; elemental analysis (C)79H47NO): theoretical value C: 92.46%, H: 4.62%, N: 1.36 percent; found value C: 92.32%, H: 4.72%, N: 1.38 percent.
EXAMPLE 7 Synthesis of Compound I-50
Figure BDA0003289634670000201
The synthetic route is as follows:
Figure BDA0003289634670000202
the intermediate M6 was used instead of M2, the molar ratio of 2-naphthaleneboronic acid to M6 was changed to 2:1, and the other starting materials and procedures were the same as in example 2, to give 25.2g of Compound I-50 as a pale yellow solid with a yield of about 65.3%.
Product MS (m/e): 773.94, respectively; elemental analysis (C)59H35NO): theoretical value C: 91.56%, H: 4.56%, N: 1.81 percent; found value C: 91.60%, H: 4.58%, N: 1.78 percent.
EXAMPLE 8 Synthesis of Compound I-60
Figure BDA0003289634670000203
The synthetic route is as follows:
Figure BDA0003289634670000204
the synthesis of the compound I-60 comprises the following specific steps:
(1) synthesis of I-60-1
150mL of toluene, 75mL of ethanol and 75mL of water were added to a 500, mlL three-necked flask equipped with a condenser, a thermometer and a magneton, followed by addition of intermediate M7(31.2g, 0.05mol), 4-biphenylboronic acid (9.9g, 0.05mol), sodium carbonate (6.3g,0.075mol), replacement of the reaction system with nitrogen, addition of 0.1g of Pd132, stirring was started, and the reaction was stopped by heating to reflux for 6 hours. The solvent is evaporated, dichloromethane is extracted, anhydrous magnesium sulfate is dried, filtration is carried out, petroleum ether/ethyl acetate (2:1) column chromatography is carried out, the solvent is dried in a rotating mode, ethyl acetate is pulped, and 29.4g of compound I-60-1 is obtained through filtration, and the yield is 83.2%.
(1) Synthesis of I-60
250ml of dioxane were added to a 500ml three-necked flask equipped with a condenser, thermometer and magneton under nitrogen protection, followed by the sequential addition of I-60-1(35.4g, 0.05mol), 2- (9-9-dimethyl-9-fluoren-2-yl) -4,4,5, 5-tetramethyl-1, 3-dioxaborane (16g, 0.05mol), cesium carbonate (39g, 0.12mol), tri-tert-butylphosphine (1.2g, 6mmol) and tris (dibenzylideneacetone) dipalladium (0.92, 1.0 mmol). After the addition, heating to reflux reaction for 6 hours, and cooling after the reaction is finished. Adjusting to neutrality, separating organic phase, extracting, drying, column chromatography, and spin-drying solvent to obtain 24.2g of compound I-60 as pale yellow solid with yield of about 81.2%.
Product MS (m/e): 866.08, respectively; elemental analysis (C)66H43NO): theoretical value C: 91.53%, H: 5.00%, N: 1.62 percent; found value C: 91.55%, H: 4.98%, N: 1.60 percent.
According to the synthetic methods of the above synthetic examples 1 to 8, other compounds among the compounds I-1 to I-80 which are typically preferred in the present invention can be synthesized by simply replacing the corresponding raw materials without changing any substantial operation.
Example 9 preparation and Performance testing of OLED devices
The organic electroluminescent device manufactured by the compound provided by the invention has a structure consistent with that of the organic electroluminescent device in the prior art, and comprises an anode layer, a plurality of light-emitting functional layers and a cathode layer; the plurality of light emitting functional layers include at least a light emitting layer. Preferably, the light-emitting functional layer includes at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, and an electron transport layer, wherein the hole transport layer contains the organic compound of the present invention.
In embodiments in which organic electroluminescent devices are specifically prepared, a substrate may be used either below the anode or above the cathode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The anode may be formed by sputtering or depositing a material serving as an anode on the substrate. For example, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and tin dioxide (SnO)2) And transparent conductive oxide materials such as zinc oxide (ZnO), and any combination thereof. The cathode may be made of magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
The plurality of light-emitting functional layers may be formed on the electrodes by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination thereof.
The following are examples of organic electroluminescent devices prepared according to the present invention using the organic compounds according to the present invention.
The embodiment provides an OLED green light device, the structure of which is as follows:
ITO/HATCN (1nm)/HT01(40nm)/I-1 compound (20nm)/EML (30nm)/Bphen (40nm)/LiF (1nm)/Al, wherein 1nm, 40nm, 20nm and the like all represent the thickness of the functional layer.
The molecular structure of each functional layer material is as follows:
Figure BDA0003289634670000221
the specific preparation process of the OLED green device in this embodiment is as follows:
(1) carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing the glass plate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent (the volume ratio is 1: 1), baking the glass plate in a clean environment until the water is completely removed, cleaning the glass plate by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
(2) placing the glass substrate with anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, performing vacuum evaporation on the anode layer film to form HATCN as a first hole injection layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 1 nm; then evaporating a second hole injection layer HT01 at the evaporation rate of 0.1nm/s and the thickness of 40 nm; then evaporating a hole transport layer by using the I-1 compound prepared in the example 1, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 20 nm;
(3) EML is evaporated on the hole transport layer in vacuum and used as a light emitting layer of the device, the EML comprises a main material and a dye material, the evaporation rate of the main material CBP is adjusted to be 0.1nm/s by using a multi-source co-evaporation method, and the dye material Ir (ppy)3The concentration of (2) is 5%, and the total film thickness of evaporation plating is 30 nm;
(4) bphen is used as an electron transport material of an electron transport layer of the device, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 40 nm;
(5) and sequentially performing vacuum evaporation on the electron transport layer to form LiF with the thickness of 1nm as an electron injection layer and an Al layer with the thickness of 150nm as a cathode of the device, thereby preparing the green light device.
The organic electroluminescent device numbered as OLED-1 was prepared according to the above procedure.
Organic electroluminescent devices, which were numbered OLED-2-OLED-8, were prepared by following the same procedure as above, except that the hole transport layer material in step (2) was replaced with only the compound I-1 prepared in example 1 with the compounds I-3, I-18, I-20, I-41, I-47, I-50, and I-60, respectively.
The adopted comparative example device is also prepared according to the same preparation steps as the OLED-1 device, and only the hole transport material in the step (2) is replaced by the existing compound PSA to obtain the comparative example device OLED-9, wherein the structural formula of the PSA is as follows:
Figure BDA0003289634670000231
the performance test data of the above devices prepared by the present invention are detailed in table 1 below.
TABLE 1
Figure BDA0003289634670000232
The data in table 1 show that, when the organic compound containing the spiro furocarbazole structure provided by the invention is used as a hole transport material, the current efficiency of the prepared device is high, the working voltage is obviously lower than that of a comparative device under the condition of the same brightness, and the current efficiency is also obviously improved, so that the organic material provided by the invention is a hole transport material with good performance.
The present invention is illustrated in detail by the above examples, but the present invention is not limited to the above detailed methods. It is obvious to those skilled in the art that any modification of the present invention, equivalent substitution of each raw material and addition of auxiliary components, selection of specific modes, etc., of the product of the present invention fall within the protection scope of the present invention.

Claims (10)

1. An organic compound having a structure represented by general formula (i):
Figure FDA0003289634660000011
wherein:
R1～R3each independently represents H, halogen, substituted or unsubstituted C1～C20A chain alkyl group of (A), a substituted or unsubstituted C3～C20Cycloalkyl, substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a);
R1～R3the groups represented by each may be the same or different; r1～R3At least one of them represents substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a);
m, n and p are each independently selected from integers of 1 to 4; preferably, m, n and p are each independently selected from 1 or 2; more preferably, m, n and p are all 1;
R4、R5each independently represents H, halogen, amino, substituted or unsubstituted C1～C20A chain alkyl group of (A), a substituted or unsubstituted C3～C20Cycloalkyl, substituted or unsubstituted C3～C60Arylamine or heteroarylamine, substituted or unsubstituted C3～C60Aryl or heteroaryl of (a); r4、R5The groups represented by each may be the same or different;
q and r are each independently selected from integers of 1 to 4; preferably, q, r are each independently selected from 1 or 2; more preferably, q and r are both 1;
R1～R5when a substituent exists on the group represented by (A), the substituents are respectively and independently selected from C1～C20Chain alkyl group of (2), C3～C20A cycloalkane group of6～C30Aryl group of (1).
2. The compound of claim 1, wherein said substituted or unsubstituted C is6～C40In the monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), the monocyclic aromatic hydrocarbon group is an aromatic hydrocarbon group containing one benzene ring; and/or the polycyclic aromatic hydrocarbon group is a polyphenyl aliphatic hydrocarbon group, biphenyl and biphenyl polycyclic aromatic hydrocarbon group, spirobifluorene group or fused ring aromatic hydrocarbon group;
preferably, said substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (A) is optionally selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted phenanthrylAny of fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted benzo (a) anthracenyl, substituted or unsubstituted benzo (b) fluoranthenyl, substituted or unsubstituted benzo (k) fluoranthenyl, substituted or unsubstituted benzo (a) pyrenyl, substituted or unsubstituted indenofluoranthenyl, substituted or unsubstituted perylenyl;
when the substituent exists, the number of the substituent is 1-3, and the substituent is respectively and independently selected from C1～C20Chain alkyl group of (2), C3～C20A cycloalkane group of1～C10Alkoxy group of (C)1～C10Thioalkoxy of, C6～C30Arylamino group of (C)3～C30Heteroarylamino of (A), C6～C30Aryl of (C)3～C30The heteroaryl group of (a).
3. The compound of claim 1 or 2, wherein said substituted or unsubstituted C is6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a) is optionally selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted indenopluoranthenyl group, a substituted or unsubstituted perylenyl group;
the substituted substituent can be 1-2, and the substituent is selected from C1～C5Chain alkyl group of (1), C3～C6Cycloalkyl, phenyl, biphenyl, naphthyl, phenanthryl, anthracyl, benzo, triphenylene, naphtho, fluoranthenyl;
preferably, said substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group is optionally selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl groupSubstituted naphthyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted perylenyl;
when substituents are present, the substituents are each independently selected from C1～C5Chain alkyl group of (1), C3～C6The number of the substituents is selected from an integer of 1 to 2.
4. A compound according to any one of claims 1 to 3, wherein R is5Is H.
5. A compound according to any one of claims 1 to 4, wherein R is4Is H.
6. A compound according to any one of claims 1 to 5 wherein R is1～R3Each independently represents H, phenyl, substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a); and said R is1～R3At least one of them represents substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a);
preferably, said substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a) is selected from any one of the following groups:
Figure FDA0003289634660000021
Figure FDA0003289634660000031
Figure FDA0003289634660000041
7. the compound of any one of claims 1 to 6, wherein the compound is selected from the group consisting of compounds represented by the following structural formulae:
Figure FDA0003289634660000042
Figure FDA0003289634660000051
Figure FDA0003289634660000061
Figure FDA0003289634660000071
Figure FDA0003289634660000081
8. use of a compound according to any one of claims 1 to 7 for the preparation of an organic electroluminescent device;
preferably, the compound is used as a hole transport material of a hole transport layer in an organic electroluminescent device.
9. An organic electroluminescent device, characterized in that a hole transport layer of the organic electroluminescent device contains the compound according to any one of claims 1 to 7.
10. An organic electronic device, wherein the functional material in the organic electronic device comprises the compound according to any one of claims 1 to 7.
CN202111159864.4A 2021-09-30 2021-09-30 Organic compound containing spiro furocarbazole structure and application thereof Pending CN113880854A (en)

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