CN111763210B - Compound containing multi-heterocyclic structure and application - Google Patents

Compound containing multi-heterocyclic structure and application Download PDF

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CN111763210B
CN111763210B CN202010661822.XA CN202010661822A CN111763210B CN 111763210 B CN111763210 B CN 111763210B CN 202010661822 A CN202010661822 A CN 202010661822A CN 111763210 B CN111763210 B CN 111763210B
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substituted
unsubstituted
aromatic hydrocarbon
hydrocarbon group
polycyclic aromatic
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CN111763210A (en
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梁现丽
程丹丹
范洪涛
段陆萌
杭德余
曹占广
班全志
陈婷
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Beijing Yanhua Jilian Optoelectronic Technology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Abstract

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

Description

Compound containing multi-heterocyclic structure and application
Technical Field
The invention relates to the technical field of materials for organic electroluminescence, and particularly discloses a novel compound containing a multi-heterocyclic structure, and also discloses application of the compound in an organic electroluminescent device.
Background
The application of the organic electroluminescent (OLED) material in the fields of information display materials, organic optoelectronic materials and the like has great research value and good application prospect. With the development of multimedia information technology, the requirements for the performance of flat panel display devices are higher and higher. The main display technologies at present are plasma display devices, field emission display devices, and organic electroluminescent display devices (OLEDs). Compared with liquid crystal display devices, OLEDs do not need backlight sources, have wider viewing angles and low power consumption, and have response speed 1000 times that of the liquid crystal display devices, so the OLEDs have wider application prospects.
Since the first time high efficiency Organic Light Emitting Diodes (OLEDs) were reported, many researchers have been working on improving the performance of OLED devices. Organic charge transport materials are an important material for OLED devices. The organic charge transport material is an organic semiconductor material which can realize the controllable directional ordered movement of carriers under the action of an electric field when the carriers (electrons or holes) are injected, thereby carrying out charge transport. The organic charge transport material mainly transports holes and is called a hole type transport material, and the organic charge transport material mainly transports electrons and is called an electron type transport material or an electron transport material for short. Organic charge transport materials have been developed to date, in which hole transport materials are more diverse and have better performance, and electron transport materials are less diverse and have poorer performance. For example, the currently commonly used electron transport material Alq3 has low electron mobility, which results in higher operating voltage of the device and serious power consumption; part of electron transport materials such as LG201 triplet level is not high, and when a phosphorescent light emitting material is used as a light emitting layer, an exciton blocking layer needs to be added, otherwise the efficiency is reduced; still other materials, such as Bphen, tend to crystallize, resulting in reduced lifetimes. These problems with electron transport materials are bottlenecks that affect the development of organic electroluminescent display devices. Therefore, the development of new electron transport materials with better performance has important practical application value.
Disclosure of Invention
The invention aims to develop an electron transport material of an organic electroluminescent device, which is applied to an OLED device, can reduce driving voltage and improve the luminous efficiency of the device.
Specifically, in a first aspect, the present invention provides a compound containing a polyheterocyclic structure, having a structure represented by general formula (i):
Figure BDA0002578874010000021
wherein:
R1～R12is optionally selected from H, halogen atom, linear or branched alkyl, cycloalkyl, substituted or unsubstituted C6～C40A monocyclic or polycyclic aromatic hydrocarbon group of (A), and R1～R12At least one of which is substituted or unsubstituted C6～C40Monocyclic aromatic hydrocarbon group or polycyclic aromatic hydrocarbon group of (a).
The halogen atom is F, Cl, Br or I.
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.
Branched chain-containing 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.
Cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like. Cycloalkyl groups having 3 to 6 carbon atoms are preferable.
C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (1), wherein the monocyclic aromatic hydrocarbon group is preferably an aromatic hydrocarbon group having 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.
Polycyclic aromatic hydrocarbon groups include, but are not limited to, groups comprising biphenyl, terphenyl, naphthalene, acenaphthene, dihydroacenaphthene, fluorene, spirobifluorene, phenanthrene, pyrene, fluoranthene, chrysene, benzo (a) anthracene, benzofluoranthene, triphenylene, benzopyrene, perylene, indenofluoranthene.
As a preferred embodiment of the present invention, said substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group in the polycyclic aromatic hydrocarbon group is a polyphenyl aliphatic hydrocarbon group, a biphenyl polycyclic aromatic hydrocarbon group, a spirobifluorene group or a fused aromatic hydrocarbon groupAny one of cyclic aromatic hydrocarbon groups; said substituted C6～C40The substituents of the monocyclic or polycyclic aromatic hydrocarbon group of (a) are optionally selected from: halogen, straight-chain or branched-chain alkyl, cycloalkyl, polycyclic aryl, monocyclic aryl, heterocyclic aryl and heterocyclic aryl, wherein the number of the substituent groups is an integer selected from 1-7.
The polycyclic aryl groups can be biphenyl, phenanthryl, fluorenyl, anthracyl, fluoranthenyl, triphenylenyl, naphthyl, and the like.
The polycyclic arylo group may be phenanthro, anthraco, fluorantheno, triphenylo, naphtho, or the like.
Monocyclic aryl is preferably phenyl.
The monocyclic aryl-and-aryl groups are preferably benzo groups.
The heteroaryl group is a group having a heteroaryl ring, and may be a benzothienyl group, a benzofuranyl group, a pyridyl group, a pyrimidyl group, a thiazolyl group, or the like.
The heterocycloaryl group may be benzothieno, benzofuro, or the like.
As a preferred embodiment of the present invention, said substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or 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 anthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted benzo (a) anthryl, 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; the substituted substituent can be 1-3, and the substituent is selected from halogen and C1-5Linear or branched alkyl, C3-8Cycloalkyl, monocyclic aryl, monocyclic arylo, polycyclic aryl, polycyclic arylo of (a); the hydrogen on the substituent may be further substituted by 1 to 2 or moreThe following optional substituents: c1-5Linear or branched alkyl, C3-8Cycloalkyl, phenyl.
As a preferred embodiment of the present invention, said substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or 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 triphenylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted indenopfluoranthenyl, substituted or unsubstituted perylenyl; the substituted substituent can be 1-3, and the substituent is selected from halogen and C1-5Linear or branched alkyl, C3-8Cycloalkyl, phenyl, biphenyl, naphthyl, naphtho, phenanthryl, benzo, triphenylene, fluoranthenyl; the hydrogen on the substituent can be further substituted by 1-2 optional substituents as follows: c1-5Linear or branched alkyl, C3-8Cycloalkyl, phenyl.
As a preferred embodiment of the present invention, said substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or 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 triphenylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted indenopfluoranthenyl, substituted or unsubstituted perylenyl; the substituted substituent can be 1-2, and the substituent is selected from C1-5Linear or branched alkyl, C3-6Cycloalkyl, phenyl, biphenyl, naphthyl, phenanthryl, benzo, triphenylene, naphtho, fluoranthenyl.
As a preferred embodiment of the present invention, said substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a) is optionally selected from the following groups:
Figure BDA0002578874010000031
Figure BDA0002578874010000041
wherein
Figure BDA0002578874010000042
Represents the linking position of the substituent to the parent nucleus.
As a preferred embodiment of the present invention, in the general formula (I), R is as defined above1～R12Except that represents substituted or unsubstituted C6～C40The remainder of the monocyclic aromatic hydrocarbon group or polycyclic aromatic hydrocarbon group(s) is a H atom.
As a preferred embodiment, in the general formula (I), R is as defined above1～R12At least one of which is selected from substituted or unsubstituted C6～C40Preferably said R is a monocyclic or polycyclic aromatic hydrocarbon radical of1～R121 to 5 of C are selected from substituted or unsubstituted6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (A), more preferably said R1～R121 to 3 of them are selected from substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a); when said R is1～R12Two or more of them are selected from substituted or unsubstituted C6～C40With monocyclic or polycyclic aromatic hydrocarbon groups, said substituted or unsubstituted C is selected6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group in (b) may be the same or different.
As a preferred embodiment, in the general formula (I), R is as defined above1～R12One of them is selected from substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; preferably R1Is substituted or unsubstitutedC of (A)6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; or, R2Is substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; or, R3Is substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; or, R6Is substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; or, R7Is substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; or, R10Is substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; or, R11Is substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), and others are all H.
As a preferred embodiment, in the general formula (I), R is as defined above1～R12Two of which are selected from substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; the R is1～R12C selected from6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group in (b) may be the same or different. Preferably R1、R3Is substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; or, R6、R8Is substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; or, R9、R11Is substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; or, R2、R7Is substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; or, R7、R10Is substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; or, R2、R10Is substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; or, R3、R11Is substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; more preferably, R2、R7Is substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; or, R7、R10Is substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; or, R2、R10Is substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), and others are all H.
As a preferred embodiment, in the general formula (I), R is as defined above1～R12Three of (1) are selected from substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; the R is1～R12C selected from6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group in (b) may be the same or different. Preferably R1～R4Wherein one is selected from substituted or unsubstituted C6～C40A monocyclic or polycyclic aromatic hydrocarbon radical of R5～R8Wherein one is selected from substituted or unsubstituted C6～C40A monocyclic or polycyclic aromatic hydrocarbon radical of R9～R12Wherein one is selected from substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), others being H; more preferably, said R1～R12In R2、R7、R10Is selected from substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), and others are all H.
As a preferred embodiment of the present invention, the compound represented by the general formula (I) is preferably selected from compounds represented by the following structural formulae:
Figure BDA0002578874010000061
Figure BDA0002578874010000071
in a second aspect, the invention provides an application of the compound containing the multi-heterocyclic structure in preparing an organic electroluminescent device.
Preferably, the compound containing the multi-heterocyclic structure is used as an electron transport material in an organic electroluminescent device.
In a third aspect, the invention provides an organic electroluminescent device, which comprises an electron transport layer, wherein the electron transport layer contains the compound containing the multi-heterocyclic ring structure in the material.
Specifically, the invention provides an organic electroluminescent device, which sequentially comprises a transparent substrate, an anode layer, a hole injection layer, a hole transport layer, an electroluminescent layer, an electron transport layer, an electron injection layer and a cathode layer from bottom to top, wherein an electron transport material of the electron transport layer comprises the compound shown in the general formula (I), namely the compound containing a multi-heterocyclic structure.
In a preferred embodiment, the thickness of the electron transport layer may be 10 to 50nm, preferably 20 to 40 nm.
In a fourth aspect, the present invention provides a display device comprising the organic electroluminescent device.
In a fifth aspect, the present invention provides a lighting apparatus comprising the organic electroluminescent device.
The invention provides a novel compound containing a multi-heterocyclic structure, which is specifically shown as a general formula (I), wherein the multi-heterocyclic structure is taken as a parent nucleus, and the parent nucleus structure has strong electron-withdrawing capability and good thermal stability; the compounds of this structure have suitable HOMO and LUMO energy levels and Eg; we have found that this is further achieved by introducing a neutral group R into the parent nucleus structure1～R12The electron transport performance of the material can be improved by changing the stacking mode among molecules.
The novel OLED material provided by the invention takes a compound containing a multi-heterocyclic ring structure as a parent nucleus, the parent nucleus structure has strong electron-withdrawing capability, and a neutral group is introduced into the parent nucleus structure to obtain the novel OLED material. The material has high electron transport performance, high film stability and proper molecular energy level, and can be applied to the field of organic electroluminescence and used as an electron transport material of an OLED device. The novel OLED material provided by the invention is a stable and efficient electronic transmission material, can effectively reduce the driving voltage of a device, improves the luminous efficiency of the device and improves the photoelectric property of the device. The novel OLED material containing the compound with the multi-heterocyclic structure can be well applied to OLED devices, and the devices have the characteristics of low driving voltage and high luminous efficiency, and have very important practical application value. The device can be applied in the fields of display and illumination.
Detailed Description
The technical solution of the present invention will be described in detail by specific examples. The following examples are intended to illustrate the present invention, but are not intended to limit the scope of the present invention, and other equivalent changes or modifications made without departing from the spirit of the present invention are intended to be included within the scope of the appended claims.
According to the preparation method provided by the present invention, a person skilled in the art can use known common means to implement, such as further selecting a suitable catalyst and a suitable solvent, and determining a suitable reaction temperature, a suitable reaction time, a suitable material ratio, and the like, which are not particularly limited in the present invention. 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.
Synthesizing intermediate M1-M10
Synthesis of intermediate M1
Figure BDA0002578874010000091
The synthetic route is as follows:
Figure BDA0002578874010000092
the specific operation steps are as follows:
(1) adding 4-chloro-1-fluoro-2-nitrobenzene (17.5g, 0.1mol) and 2-bromo-4-chloroaniline (30.8g, 0.15mol) into a 2L three-necked bottle with mechanical stirring, protecting with argon, heating to 180 ℃, keeping the temperature for reaction for more than 30 hours, wherein the color of the reaction solution gradually becomes red in the reaction process, and finally gradually becomes deep red. After the reaction is finished, an organic phase is separated, extracted, dried, subjected to column chromatography, and subjected to spin-drying to obtain 30g of orange-red solid M-01 with the yield of 83%.
(2) In a 1L three-necked flask equipped with a mechanical stirrer, M-01(36.0g, 0.1mol), sodium sulfide nonahydrate (96g, 0.4mol), ethanol (200mL), and water (100mL) were added, and the mixture was heated to reflux under nitrogen protection, and the reaction was terminated after refluxing for 3 hours. Separating organic phase, extracting, drying, column chromatography and spin-drying solvent to obtain 26.5g white solid M-02 with yield of 80%.
(3) In a 1L three-necked flask with mechanical stirring, adding M-02(33.0g, 0.1mol) and 300mL of acetone for complete dissolution, adding a solution of KOH (11.2g, 0.2mol) dissolved in water (50mL), slowly dropwise adding 2-bromo-4-chlorobenzoyl chloride (25.2g, 0.1mol) into the reaction flask, gradually precipitating solids in the reaction flask, reacting at normal temperature for 2 hours after the dropwise adding is finished, and finishing the reaction. Adjusting to neutrality, separating an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 43.8g of white solid M-03 with the yield of 79%.
(4) Adding M-03(54.8g, 0.1mol) and 200mL of glycol ether into a 1L three-necked flask, gradually heating to reflux under the protection of nitrogen, gradually dissolving the solid, magnetically stirring, keeping the temperature and reacting for 3 hours, and finishing the reaction. The organic phase was separated, extracted, dried, column chromatographed, and the solvent was spin-dried to give 40g of M-04 as a pale red solid in 76% yield.
(5) M-04(53.0g, 0.1mol) and THF were added under nitrogen in a 2L three-necked flask800mL, cooling to-78 ℃, slowly adding n-butyllithium (100mL, 0.25mol) dropwise under stirring for about 30mins, flushing a dropping funnel with 50mL of THF after dropping, keeping the temperature at-78 ℃ for 1.5 hours after dropping, and then adding 20g of freshly sublimed anhydrous AlCl3The mixture is kept at low temperature for 20 minutes, anhydrous acetone (30mL, 0.4mol) is slowly dropped, then a small amount of THF is used for washing a dropping funnel, the temperature is kept for 1 hour after the addition, then the temperature is slowly raised to room temperature, the mixture is stirred at room temperature for reaction for 4 hours, and the reaction is finished. Adjusting to neutrality, separating the organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 25g of white solid, namely intermediate M1, with the yield of 61%.
Product MS (m/e): 412.03, respectively; elemental analysis (C)22H15Cl3N2): theoretical value C: 63.87%, H: 3.65%, N: 6.77 percent; found value C: 63.61%, H: 3.42%, N: 6.50 percent.
Synthesis of intermediate M2
Figure BDA0002578874010000101
By using
Figure BDA0002578874010000102
Instead of the former
Figure BDA0002578874010000107
And selecting a proper material ratio, and synthesizing other raw materials and steps which are the same as the intermediate M1 to obtain the intermediate M2.
Product MS (m/e): 378.07, respectively; elemental analysis (C)22H16Cl2N2): theoretical value C: 69.67%, H: 4.25%, N: 7.39 percent; found value C: 69.41%, H: 4.00%, N: 7.10 percent.
Synthesis of intermediate M3
Figure BDA0002578874010000104
By using
Figure BDA0002578874010000105
Respectively replace
Figure BDA0002578874010000106
And selecting a proper material ratio, and synthesizing other raw materials and steps which are the same as the intermediate M1 to obtain the intermediate M3.
Product MS (m/e): 378.07, respectively; elemental analysis (C)22H16Cl2N2): theoretical value C: 69.67%, H: 4.25%, N: 7.39 percent; found value C: 69.42%, H: 4.01%, N: 7.12 percent.
Synthesis of intermediate M4
Figure BDA0002578874010000111
By using
Figure BDA0002578874010000112
Respectively replace
Figure BDA0002578874010000113
And selecting a proper material ratio, and synthesizing other raw materials and steps which are the same as the intermediate M1 to obtain the intermediate M4.
Product MS (m/e): 378.07, respectively; elemental analysis (C)22H16Cl2N2): theoretical value C: 69.67%, H: 4.25%, N: 7.39 percent; found value C: 69.41%, H: 4.00%, N: 7.08 percent.
Synthesis of intermediate M5
Figure BDA0002578874010000114
By using
Figure BDA0002578874010000115
Respectively replace
Figure BDA0002578874010000116
Selecting suitable substancesThe material ratio, other raw materials and steps are the same as those of the intermediate M1, and the intermediate M5 is obtained.
Product MS (m/e): 378.07, respectively; elemental analysis (C)22H16Cl2N2): theoretical value C: 69.67%, H: 4.25%, N: 7.39 percent; found value C: 69.43%, H: 4.00%, N: 7.11 percent.
Synthesis of intermediate M6
Figure BDA0002578874010000117
By using
Figure BDA0002578874010000118
Respectively replace
Figure BDA0002578874010000119
And selecting a proper material ratio, and synthesizing other raw materials and steps which are the same as the intermediate M1 to obtain the intermediate M6.
Product MS (m/e): 344.11, respectively; elemental analysis (C)22H17ClN2): theoretical value C: 76.63%, H: 4.97%, N: 8.12 percent; found value C: 76.39%, H: 4.72%, N: 7.93 percent.
Synthesis of intermediate M7
Figure BDA0002578874010000121
By using
Figure BDA0002578874010000122
Respectively replace
Figure BDA0002578874010000123
And selecting a proper material ratio, and obtaining the intermediate M7 by the same synthesis of other raw materials and steps as the intermediate M1.
Product MS (m/e): 344.11, respectively; elemental analysis (C)22H17ClN2): theoretical value C: 76.63%, H: 4.97%, N: 8.12 percent; fruit of Chinese wolfberryMeasured value C: 76.39%, H: 4.72%, N: 7.93 percent.
Synthesis of intermediate M8
Figure BDA0002578874010000124
By using
Figure BDA0002578874010000125
Respectively replace
Figure BDA0002578874010000126
And selecting a proper material ratio, and synthesizing other raw materials and steps which are the same as the intermediate M1 to obtain the intermediate M8.
Product MS (m/e): 344.11, respectively; elemental analysis (C)22H17ClN2): theoretical value C: 76.63%, H: 4.97%, N: 8.12 percent; found value C: 76.36%, H: 4.73%, N: 7.90 percent.
Synthesis of intermediate M9
Figure BDA0002578874010000127
The synthetic route is as follows:
Figure BDA0002578874010000131
(1) synthesis of intermediate M9-04:
by using
Figure BDA0002578874010000132
Respectively replace
Figure BDA0002578874010000133
Figure BDA0002578874010000134
Selecting proper material ratio, and obtaining the intermediate M by the same synthesis method of the intermediate M1 and other raw materials and steps9-04。
(2) Synthesis of intermediate M9:
under the protection of nitrogen, M9-04(51.0g, 0.1mol) and THF 800mL are added into a 2L three-necked bottle, the mixture is cooled to-78 ℃, n-butyllithium (44mL, 0.11mol) is slowly dropped under stirring for about 30mins, the dropping funnel is flushed with 50mL of THF after dropping, the temperature is kept at-78 ℃ for 1.5 hours after dropping, then anhydrous acetone (30mL, 0.4mol) is slowly dropped, then a small amount of THF is used for flushing the dropping funnel, the temperature is kept for 1 hour after adding, then the temperature is slowly raised to room temperature, the reaction is stirred at room temperature for 4 hours, and the reaction is finished. Adjusting to neutrality, separating organic phase, extracting, drying with anhydrous molecular sieve, and pumping off solvent to obtain yellow solid.
This solid was dissolved in 300ml of dry CH2Cl2Cooling to 0 ℃ in an ice water bath, slowly dropwise adding methanesulfonic acid (19.2g, 0.2mol), after dropwise adding, continuously stirring at 0 ℃ for 2 hours, then heating to room temperature, continuously stirring for 1 hour, detecting by TLC to complete the reaction, adding saturated NaHCO3 solution to quench the reaction, adjusting to be neutral, washing twice with dichloromethane, combining organic solvents, drying with anhydrous magnesium sulfate, performing column chromatography, and spin-drying the solvents to obtain 29.5g of white solid, namely the intermediate M9, with the yield of 70%.
Product MS (m/e): 422.02, respectively; elemental analysis (C)22H16BrClN2): theoretical value C: 62.36%, H: 3.81%, N: 6.61 percent; found value C: 62.10%, H: 3.55%, N: 6.38 percent.
Synthesis of intermediate M10
Figure BDA0002578874010000141
By using
Figure BDA0002578874010000142
Respectively replace
Figure BDA0002578874010000143
And selecting a proper material ratio, and synthesizing other raw materials and steps which are the same as the intermediate M9 to obtain the intermediate M10.
Product MS (m/e): 422.02, respectively; elemental analysis (C)22H16BrClN2): theoretical value C: 62.36%, H: 3.81%, N: 6.61 percent; found value C: 62.11%, H: 3.54%, N: 6.36 percent.
Example 1
Figure BDA0002578874010000144
The synthetic route is as follows:
Figure BDA0002578874010000145
the synthesis of the compound I-1 comprises the following specific steps:
A2L three-necked flask was taken, and magnetic stirring was carried out, after nitrogen substitution, M1(41.2g, 0.1mol), phenylboronic acid (36.6g, 0.3mol), cesium carbonate (117g, 0.36mol) and 800ml of dioxane were sequentially added, and stirring was started. After nitrogen replacement again, (2.2g, 11mmol) tri-tert-butylphosphine and (4.1g, 4.5mmol) tris (dibenzylideneacetone) dipalladium were added. After the addition, heating and raising the temperature, controlling the temperature to be 80-90 ℃ for reaction for 4 hours, and cooling after the reaction is finished. Adjusting to neutrality, separating an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 38.7g of pale yellow solid with the yield of about 72 percent.
Product MS (m/e): 538.24, respectively; elemental analysis (C)40H30N2): theoretical value C: 89.19%, H: 5.61%, N: 5.20 percent; found value C: 88.96%, H: 5.39%, N: 4.98 percent.
Example 2
Figure BDA0002578874010000151
The synthetic route is as follows:
Figure BDA0002578874010000152
synthesis of Compound I-8: m2 was used instead of M1, and 3, 4-dimethylphenylboronic acid was used instead of phenylboronic acid, and the other raw materials and procedures were the same as in example 1, with the selection of an appropriate material ratio, to obtain 41.4g of a pale yellow solid with a yield of about 80%.
Product MS (m/e): 518.27, respectively; elemental analysis (C)38H34N2): theoretical value C: 87.99%, H: 6.61%, N: 5.40 percent; found value C: 87.73%, H: 6.39%, N: 5.18 percent.
Example 3
Figure BDA0002578874010000153
The synthetic route is as follows:
Figure BDA0002578874010000154
synthesis of Compound I-10: m3 was used instead of M1, 4-cyclopentylphenylboronic acid was used instead of phenylboronic acid, and the other raw materials and procedures were the same as in example 1, except that the appropriate material ratio was selected, whereby 49.6g of a pale yellow solid was obtained with a yield of about 83%.
Product MS (m/e): 598.33, respectively; elemental analysis (C)44H42N2): theoretical value C: 88.25%, H: 7.07%, N: 4.68 percent; found value C: 88.02%, H: 6.79%, N: 4.38 percent.
Example 4
Figure BDA0002578874010000161
The synthetic route is as follows:
Figure BDA0002578874010000162
synthesis of Compound I-14: m4 is used for replacing M1, biphenyl boric acid is used for replacing phenylboronic acid, a proper material ratio is selected, other raw materials and steps are the same as those of example 1, 43.6g of light yellow solid is obtained, and the yield is about 71%.
Product MS (m/e): 614.27, respectively; elemental analysis (C)46H34N2): theoretical value C: 89.87%, H: 5.57%, N: 4.56 percent; found value C: 89.65%, H: 5.34%, N: 4.26 percent.
Example 5
Figure BDA0002578874010000163
The synthetic route is as follows:
Figure BDA0002578874010000164
synthesis of Compound I-24: m5 was used instead of M1, and 2-naphthalene boronic acid was used instead of phenylboronic acid, and the other raw materials and procedures were the same as in example 1, with the selection of a suitable material ratio, to obtain 41.6g of a pale yellow solid with a yield of about 74%.
Product MS (m/e): 562.24, respectively; elemental analysis (C)42H30N2): theoretical value C: 89.65%, H: 5.37%, N: 4.98 percent; found value C: 89.42%, H: 5.16%, N: 4.74 percent.
Example 6
Figure BDA0002578874010000171
The synthetic route is as follows:
Figure BDA0002578874010000172
synthesis of Compound I-34: m6 was used instead of M1 and triphenylen-2-yl boronic acid was used instead of phenylboronic acid, and the other raw materials and procedures were the same as in example 1, selecting an appropriate material ratio, to obtain 45.0g of a pale yellow solid with a yield of about 84%.
Product MS (m/e): 536.23, respectively; elemental analysis (C)40H28N2): theoretical value C: 89.52%, H: 5.26Percent, N: 5.22 percent; found value C: 89.26%, H: 5.03%, N: 5.00 percent.
Example 7
Figure BDA0002578874010000173
The synthetic route is as follows:
Figure BDA0002578874010000174
synthesis of Compound I-41: m7 was used instead of M1, 9, 9' -spirobifluorene-2-boronic acid instead of phenylboronic acid, and the other raw materials and procedures were the same as in example 1, with the selection of an appropriate material ratio, to obtain 51.8g of a pale yellow solid with a yield of about 83%.
Product MS (m/e): 624.26, respectively; elemental analysis (C)47H32N2): theoretical value C: 90.35%, H: 5.16%, N: 4.48 percent; found value C: 90.12%, H: 4.96%, N: 4.23 percent.
Example 8
Figure BDA0002578874010000181
The synthetic route is as follows:
Figure BDA0002578874010000182
synthesis of Compound I-43: m8 was used in place of M1, and indeno [1,2,3-cd ] fluoranthen-5-ylboronic acid was used in place of phenylboronic acid, and the other raw materials and steps were the same as in example 1, except that the appropriate material ratio was selected, whereby 47.3g of a pale yellow solid was obtained with a yield of about 81%.
Product MS (m/e): 584.23, respectively; elemental analysis (C)44H28N2): theoretical value C: 90.38%, H: 4.83%, N: 4.79 percent; found value C: 90.11%, H: 4.62%, N: 4.54 percent.
Example 9
Figure BDA0002578874010000183
The synthetic route is as follows:
Figure BDA0002578874010000184
the synthesis of the compound I-49 comprises the following specific steps:
into a 1L three-necked flask, M9(44.4g, 0.1mol), 4-isopropylphenylboronic acid (16.4g, 0.1mol), sodium carbonate (21.2g,0.2mol), toluene (150 mL), ethanol (150 mL), and water (150 mL) were charged, and Pd (PPh) was added after the reaction system was purged with nitrogen3)4(11.5g, 10 mmol). The reaction was heated under reflux (temperature in the system: about 78 ℃ C.) for 3 hours to stop the reaction. The solvent is evaporated off, 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 filtration is carried out to obtain 37.4g of light yellow solid I-49-1 with the yield of about 81%.
A1L three-necked flask was equipped with magnetic stirring, and after nitrogen substitution, I-49-1(48.4g, 0.1mol), biphenylboronic acid (19.8g, 0.1mol), cesium carbonate (39g, 0.12mol) and dioxane (400 ml) were sequentially added, followed by stirring. After nitrogen replacement again, (0.8g, 4mmol) tri-tert-butylphosphine and (1.4g, 1.5mmol) tris (dibenzylideneacetone) dipalladium were added. After the addition, heating and raising the temperature, controlling the temperature to be 80-90 ℃ for reaction for 4 hours, and cooling after the reaction is finished. Adjusting to neutrality, separating organic phase, extracting, drying, column chromatography, and spin-drying solvent to obtain 43.5g pale yellow solid I-49 with yield of about 75%.
Product MS (m/e): 580.29, respectively; elemental analysis (C)43H36N2): theoretical value C: 88.93%, H: 6.25%, N: 4.82%; found value C: 88.69%, H: 6.01%, N: 4.58 percent.
Example 10
Figure BDA0002578874010000191
The synthetic route is as follows:
Figure BDA0002578874010000192
synthesis of Compound I-50: replacement of M9 with M10, (4-phenylnaphthalen-1-yl) boronic acid for 4-isopropylphenylboronic acid, [1, 1': 3', 1' -terphenyl ] -5' -ylboronic acid was substituted for biphenylboronic acid, the appropriate material ratios were chosen and the other raw materials and procedures were the same as in example 9, yielding 53.3g of a pale yellow solid I-50 with a yield of about 72%.
Product MS (m/e): 740.32, respectively; elemental analysis (C)56H40N2): theoretical value C: 90.78%, H: 5.44%, N: 3.78 percent; found value C: 90.52%, H: 5.20%, N: 3.53 percent.
According to the synthesis schemes of the above examples 1 to 10, other compounds in I-1 to I-52 can be synthesized by simply replacing the corresponding raw materials without changing any substantial operation.
Example 11
The embodiment provides a group of OLED green light devices, and the device structure is as follows: ITO/HATCN (1nm)/HT01(40nm)/NPB (20nm)/EML (30 nm)/any of the compounds (40nm)/LiF (1nm)/Al provided in examples 1 to 10, the preparation process comprising:
(1) ultrasonically cleaning a glass substrate coated with an ITO transparent conductive thin film layer in cleaning solution, ultrasonically treating the glass substrate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent (the volume ratio is 1: 1), baking the glass substrate in a clean environment until the water is completely removed, etching and cleaning the glass substrate by using an ultraviolet lamp, and bombarding the surface by using low-energy cationic beams;
(2) placing the glass substrate with the 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, a layer of NPB is evaporated on the hole injection layer film to form a hole transport layer, the evaporation rate is 0.1nm/s,the thickness of the evaporation film is 20 nm; wherein the structural formulas of HATCN, HT01 and NPB are as follows:
Figure BDA0002578874010000201
(3) vacuum evaporating EML on the hole transport layer to serve as a light emitting layer of the device, wherein the EML comprises a main material and a dye material, placing the main material CBP serving as the light emitting layer in a chamber of vacuum vapor deposition equipment by using a multi-source co-evaporation method, and adding Ir (ppy) serving as a dopant3Placing in another chamber of vacuum vapor deposition equipment, and adjusting evaporation rate of main material to 0.1nm/s, Ir (ppy)3The concentration of (2) is 10%, and the total film thickness of evaporation plating is 30 nm; wherein CBP, Ir (ppy)3The structural formula of (A) is as follows:
Figure BDA0002578874010000202
(4) evaporating an electron transport layer on the luminescent layer, taking any one of the compounds provided in the embodiments 1 to 10 as an electron transport material of the electron transport layer of the device, and evaporating, wherein the evaporation rate is 0.1nm/s, and the total thickness of the evaporated film is 40 nm;
(5) sequentially vacuum evaporating LiF with the thickness of 1nm on the electron transport layer to serve as an electron injection layer of the device, continuously evaporating a layer of Al on the electron injection layer to serve as a cathode of the device, and evaporating the film with the thickness of 150 nm; obtaining a series of OLED-1-OLED-10 devices provided by the invention.
According to the same procedure as above, only the electron transport material in the step (4) was replaced with the following comparative compound, the structural formula of which is shown below, to obtain a comparative device OLED-11.
Figure BDA0002578874010000203
Comparative compounds.
The performance of the obtained devices OLED-1 to OLED-11 is detected, and the detection results are shown in Table 1.
TABLE 1
Figure BDA0002578874010000211
As can be seen from the results in the table above, the green fluorescent devices OLED-1 to OLED-10 prepared by using the compound provided by the invention have higher current efficiency, and the working voltage is obviously lower than that of the device OLED-11 using the comparative compound Bphen as an electron transport material under the condition of the same brightness. The results show that the organic material shown in the general formula (I) provided by the invention is used for an organic electroluminescent device, can effectively reduce the driving voltage and improve the current efficiency, and is an electron transport material with good performance.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.

Claims (9)

1. A compound containing a polyheterocyclic structure, having a structure represented by general formula (i):
Figure FDA0003184548180000011
wherein:
R1～R12is optionally selected from H, halogen atom, linear or branched alkyl, cycloalkyl, substituted or unsubstituted C6～C40A monocyclic or polycyclic aromatic hydrocarbon group of (A), and R1～R12At least one of which is substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a);
wherein, said substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or polycyclic aromatic hydrocarbon group is optionally selectedFrom: 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 triphenylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted indenopfluoranthenyl, substituted or unsubstituted perylenyl; the substituted substituent can be 1-2, and the substituent is selected from C1-5Linear or branched alkyl, C3-6Cycloalkyl, phenyl, biphenyl, naphthyl, phenanthryl, benzo, triphenylene, naphtho, fluoranthenyl.
2. The compound of claim 1, wherein said substituted or unsubstituted C is6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a) is optionally selected from the following groups:
Figure FDA0003184548180000012
Figure FDA0003184548180000021
3. a compound according to claim 1 or 2, wherein R is1～R12Except that represents substituted or unsubstituted C6～C40The rest of the monocyclic aromatic hydrocarbon group or polycyclic aromatic hydrocarbon group is H atom;
the R is1～R12In, R1、R2、R3、R6、R7、R10Or R11Is substituted or unsubstituted C6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), the remainder being H atoms;
or, said R1～R12In, R1And R3、R2And R7、R7And R10、R2And R10、R6And R8、R9And R11Or R3And R11Is substituted or unsubstituted C6～C40With the remainder being H atoms, said substituted or unsubstituted C being selected6～C40The monocyclic aromatic hydrocarbon groups or polycyclic aromatic hydrocarbon groups of (a) may be the same or different;
or, said R1～R12In, R1～R4One of them is substituted or unsubstituted C6～C40A monocyclic or polycyclic aromatic hydrocarbon radical of R5～R8One of them is substituted or unsubstituted C6～C40A monocyclic or polycyclic aromatic hydrocarbon radical of R9～R12One of them is substituted or unsubstituted C6～C40With respect to the monocyclic or polycyclic aromatic hydrocarbon group of (A), the others being H, said substituted or unsubstituted C being selected6～C40The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group in (b) may be the same or different.
4. The compound of claim 1, wherein the compound is selected from the group consisting of compounds represented by the following structural formulae:
Figure FDA0003184548180000031
Figure FDA0003184548180000041
5. use of the compound containing a polyheterocyclic structure according to any one of claims 1 to 4 in the preparation of an organic electroluminescent device.
6. The use according to claim 5, wherein the compound containing a polyheterocyclic structure is used as an electron transport material in an organic electroluminescent device.
7. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises an electron transport layer, and the electron transport layer comprises a compound containing a polyheterocycle structure according to any one of claims 1 to 4.
8. A display device comprising the organic electroluminescent element according to claim 7.
9. An illumination device comprising the organic electroluminescent element according to claim 7.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20170237015A1 (en) * 2016-02-11 2017-08-17 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
CN111039954A (en) * 2019-11-28 2020-04-21 北京燕化集联光电技术有限公司 Novel organic material and application thereof in device

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20170237015A1 (en) * 2016-02-11 2017-08-17 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
CN111039954A (en) * 2019-11-28 2020-04-21 北京燕化集联光电技术有限公司 Novel organic material and application thereof in device

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