CN114605434A - Organic compound and application thereof - Google Patents

Organic compound and application thereof Download PDF

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CN114605434A
CN114605434A CN202210306718.8A CN202210306718A CN114605434A CN 114605434 A CN114605434 A CN 114605434A CN 202210306718 A CN202210306718 A CN 202210306718A CN 114605434 A CN114605434 A CN 114605434A
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heteroaryl
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王家豪
曹占广
张小玲
呼建军
石志亮
张朝霞
杭德余
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Beijing Yanhua Jilian Optoelectronic Technology Co ltd
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Abstract

The invention relates to an organic compound, belongs to the technical field of materials for light-emitting display, and particularly discloses an organic light-emitting material shown as the following formula, wherein R in the formula (I)1、R2、R3And R4At least one of the two is substituted or unsubstituted C5-C60 heteroaryl with electron withdrawing property. When the compound is applied to an OLED device and used as an electron transport layer material, the photoelectric property of the device can be effectively improved.

Description

Organic compound and application thereof
Technical Field
The invention relates to an organic luminescent material, belongs to the technical field of materials for luminescent display, and particularly discloses an organic material taking a spiroheterocyclic carbazole structure as a parent nucleus structure, and also discloses application of the organic material 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 and has the advantages of low driving voltage and high luminous efficiency.
In a first aspect, the present invention provides an organic compound, specifically an organic material containing a spiroheterocyclic carbazole structure, having a structure represented by general formula (i):
Figure BDA0003565809650000021
in the general formula (I), X is selected from O, S, Se and NRX1、CRX2RX3、PRX4Or SiRX5RX6；
RX1、RX2、RX3、RX4、RX5And RX6Each independently selected from one of halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 straight chain or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; rX2And RX3Can be connected in a ring between RX5And RX6Can be connected into a ring;
r is selected from one of substituted or unsubstituted C1-C20 straight chain or branched chain alkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
R1、R2、R3and R4Each independently represents a substituent group ranging from mono-substitution to the maximum allowable number, R1、R2、R3And R4Each independently selected from one of hydrogen, deuterium, halogen, amino, substituted or unsubstituted C1-C20 straight chain or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroaryl amino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C5-C60 heteroaryl with electron withdrawing property;
and R is1、R2、R3And R4At least one of which is a substituted or unsubstituted heteroaryl group having electron withdrawing properties of C5-C60, said heteroaryl group containing at least one heteroatom selected from the group consisting of N atom, S atom and O atom, said aromatic group being linked to the parent nucleus represented by formula (I) through a C atom;
r is as defined above1、R2、R3、R4、R、RX1、RX2、RX3、RX4、RX5And RX6The substituted substituent groups are respectively and independently selected from one or the combination of two of deuterium, halogen, C1-C20 straight-chain or branched-chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, nitro, cyano, amino, hydroxyl, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl and C3-C60 heteroaryl.
As a preferred embodiment, said X is selected from O, S, Se; more preferably, X is selected from O, S.
As a preferred embodiment, R is selected from substituted or unsubstituted aryl groups of C6-C30; more preferably, R is selected from substituted or unsubstituted phenyl, and the substituent substituted on R is selected from one or two of deuterium, fluorine, cyano, amino, C1-C10 straight-chain or branched-chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl and C3-C60 heteroaryl.
As a preferred embodiment, said R1、R2、R3And R4At least one of the aryl is substituted or unsubstituted C5-C60 heteroaryl with electron withdrawing property, and the heteroaryl is selected from at least one or the combination of two of the following groups: a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted 1, 10-phenanthrolinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted benzopyrazinyl group, a substituted or unsubstituted s-triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group; the substituted substituent on the heteroaryl is 1-4, and the substituted substituent on the heteroaryl is respectively and independently selected from one or a combination of two of C1-C20 straight-chain or branched-chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, nitro, cyano, amino, hydroxyl, C1-C20 alkyl silicon base, C1-C20 alkyl amino, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl and C3-C60 heteroaryl.
Further preferably, R is1、R2、R3And R4At least one selected from the group consisting of substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzopyrazinyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted 1, 10-phenanthrolinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted s-triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, and substituted or unsubstituted pyrimidyl; 1 to 3 substituents on the heteroaryl are respectively and independently selected from methyl, ethyl, propyl, isopropyl, and the substituted with 1-substituted or a substituted aryl, and the substituted aryl,Propyl, butyl, isopropyl, tert-butyl, phenyl, biphenyl, quinazolinyl, benzopyrazinyl, triazolyl, oxadiazolyl, benzo, naphthoyl, benzimidazolyl, naphthyl, pyridyl, pyridoyl, pyrrolyl, pyrrolo, imidazolyl, imidazo, pyrazolyl, pyrazolo, diazinyl, diazino, 1, 10-phenanthroline, s-triazinyl, fluorenyl, oxyfluorenyl, thiofluorenyl, quinolyl, isoquinolyl, carbazolyl or a combination of two thereof.
As a preferred embodiment, said R1、R2、R3And R4At least one of the aryl is substituted or unsubstituted C5-C60 heteroaryl with electron withdrawing property, and the heteroaryl is selected from one of the following groups:
Figure BDA0003565809650000031
Figure BDA0003565809650000041
Figure BDA0003565809650000051
Figure BDA0003565809650000061
wherein "- -" represents a substituted bit.
In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or a plurality of substituents, and when a plurality of substituents are present, different substituents may be selected from the group.
In the invention, the substituted or unsubstituted C5-C60 heteroaryl with electron withdrawing property can contain no five-membered ring or at least one five-membered ring, and the heteroatom is optionally selected from N atom, S atom or O atom; the substituted or unsubstituted C5-C60 heteroaryl with electron withdrawing property can contain one, two or three five-membered heterocyclic rings; the five-membered heterocycle contains one, two or three heteroatoms; when the substituted or unsubstituted electron-withdrawing C5 to C60 heteroaryl group contains a plurality of heteroatoms, the heteroatoms may be the same or different. As a preferred embodiment, the substituted or unsubstituted C5 to C60 heteroaryl group having electron withdrawing properties is selected from the group consisting of at least one of the following groups: substituted or unsubstituted quinazolinyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted 1, 10-phenanthrolinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted benzopyrazinyl, substituted or unsubstituted s-triazinyl, substituted or unsubstituted quinolyl, and substituted or unsubstituted isoquinolyl. The number of the substituted substituent groups on the heteroaryl is an integer from 1 to 4; the substituent groups substituted on the heteroaryl are respectively and independently selected from one or two combinations of C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, nitro, cyano, amino, hydroxyl, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl and C3-C60 heteroaryl.
In the present specification, unless otherwise specified, both aryl and heteroaryl groups include monocyclic and fused rings. The monocyclic aryl group means that at least one phenyl group is contained in the molecule, and when at least two phenyl groups are contained in the molecule, the phenyl groups are independent of each other and are linked by a single bond, such as phenyl, biphenylyl, terphenylyl, and the like, for example; the fused ring aryl group means that at least two benzene rings are contained in the molecule, but the benzene rings are not independent of each other, but common ring sides are fused with each other, and exemplified by naphthyl, anthryl and the like; monocyclic heteroaryl refers to a compound having at least one heteroaryl group in the molecule, and when a heteroaryl group and other groups (e.g., aryl, heteroaryl, alkyl, etc.) are present in the molecule, the heteroaryl and other groups are independently linked by a single bond, illustratively pyridine, furan, thiophene, etc.; fused ring heteroaryl refers to a fused ring of at least one phenyl group and at least one heteroaryl group, or, fused ring of at least two heteroaryl rings, illustratively quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, and the like.
In the present specification, the expression of Ca to Cb means that the group has carbon atoms of a to b, and the carbon atoms do not generally include the carbon atoms of the substituents unless otherwise specified.
In the present specification, the substituted or unsubstituted C6 to C60 aryl group is preferably a substituted or unsubstituted C6 to C30 aryl group, more preferably a C6 to C20 aryl group, and more preferably a group selected from the group consisting of a phenyl group, a naphthyl group, an anthryl group, a benzanthryl group, a phenanthryl group, a benzophenanthryl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, a tetracenyl group, a pentacenyl group, a benzopyrenyl group, a biphenyl group, an idophenyl group, a terphenyl group, a quaterphenyl group, a fluorenyl group, a spirobifluorenyl group, an acenaphthenyl group, a dihydrophenanthrenyl group, a dihydropyrenyl group, a tetrahydropyrenyl group, a cis-or trans-indenofluorenyl group, a trimeric indenyl group, an isotridecyl group, a spiro trimeric indenyl group, and a spiro isotridec indenyl group. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl, and 4-biphenyl; terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracene group is selected from 1-anthracene group, 2-anthracene group and 9-anthracene group; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracene group is selected from the group consisting of 1-tetracene, 2-tetracene, and 9-tetracene. Preferred examples of the aryl group in the present invention include phenyl, biphenyl, terphenyl and naphthylAnthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof, fluoranthenyl, triphenylene, pyrenyl, perylenyl,
Figure BDA0003565809650000071
A group of the group consisting of a phenyl group and a tetracenyl group. The biphenyl group is selected from the group consisting of 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracene group is selected from the group consisting of 1-anthracene group, 2-anthracene group, and 9-anthracene group; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9, 9 '-dimethylfluorene, 9' -spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracene group is selected from the group consisting of 1-tetracene, 2-tetracene, and 9-tetracene.
The heteroatom in the present specification is generally referred to as being selected from N, O, S, P, Si and Se, preferably from N, O, S.
In the present specification, the substituted or unsubstituted C3 to C60 heteroaryl group is preferably a substituted or unsubstituted C3 to C30 heteroaryl group, more preferably a C4 to C20 heteroaryl group, more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, and the like, and specific examples thereof include: furyl, thienyl, pyrrolyl, pyridyl, benzofuryl, benzothienyl, isobenzofuryl, isobenzothienyl, indolyl, isoindolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalimidazolyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzpyridazinyl, Pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazananthracenyl, 2, 7-diazpyrenyl, 2, 3-diazpyrenyl, 1, 6-diazenyl, 1, 8-diazenyl, 4,5, 9, 10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2, 4, 5-tetrazinyl, 1,2, 3, 4-tetrazinyl, 1,2, 3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazole, and the like. Preferred examples of the heteroaryl group in the present invention include furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole or indolocarbazole.
The aryloxy group in the present specification includes a monovalent group composed of the above aryl group, heteroaryl group and oxygen.
In the present specification, examples of the C1 to C20 alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, adamantyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2, 2, 2-trifluoroethyl and the like.
In the present specification, the cycloalkyl group having 3 to 20 includes monocycloalkyl groups and polycycloalkyl groups, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
In the present specification, examples of the C1 to C20 alkoxy group include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like, among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutyloxy, isopentyloxy, more preferably methoxy, are preferred.
Examples of the C1-C20 silyl group in the present specification include silyl groups substituted with the groups exemplified for the C1-C20 alkyl groups, and specifically include: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, t-butyldimethylsilyl, t-butyldiphenylsilyl and the like.
In the present specification, examples of the halogen include: fluorine, chlorine, bromine, iodine, and the like.
As a preferred embodiment of the present invention, the compound represented by the general formula (I) is arbitrarily selected from compounds represented by the following structural formulae, and these compounds are merely representative and do not limit the scope of the present invention:
Figure BDA0003565809650000081
Figure BDA0003565809650000091
Figure BDA0003565809650000101
Figure BDA0003565809650000111
Figure BDA0003565809650000121
Figure BDA0003565809650000131
Figure BDA0003565809650000141
in a second aspect, the invention provides an application of the organic material containing the spiroheterocyclic carbazole structure in preparation of organic electroluminescent devices.
Preferably, the organic material is used as an electron transport layer material in an organic electroluminescent device.
In a third aspect, the present invention provides an organic electroluminescent device comprising an electron transport layer containing the organic material according to the present invention.
More 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 the electron transport layer comprises the compound shown in the general formula (I) provided by the invention. The thickness of the electron transport layer can be 10-50 nm, and preferably 20-40 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 an organic compound containing a spiro heterocyclic carbazole structure with a novel structure, wherein a parent nucleus of the compound has strong electron withdrawing capability and good thermal stability, the electron injection capability can be effectively enhanced and the electron transport performance can be improved by designing the connection of the parent nucleus of the compound and an electron withdrawing group, and the structure has proper HOMO and LUMO energy levels and Eg, so that the structure has good film stability and proper molecular energy levels. Meanwhile, the compound has the advantages of good thermal stability, stability and high efficiency.
The material provided by the invention can be applied to the field of organic electroluminescence, and experiments prove that the organic material provided by the invention is applied to an OLED device, for example, the organic material is applied to the OLED device as an electron transport layer material, so that the driving voltage can be reduced, the luminous efficiency of the device can be improved, the photoelectric property of the device can be effectively improved, and the manufactured OLED device can be applied to the field of display or 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.
Synthesis of intermediates
Synthesis of intermediate M1
Figure BDA0003565809650000151
The synthetic route is as follows:
Figure BDA0003565809650000152
the specific operation steps are as follows:
(1) 2-bromobenzo [ b ] thiophene (21.3g, 0.1mol), methyl 2- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) benzoate (26.2g, 0.1mol), sodium carbonate (26.5g,0.25mol), toluene 200mL, ethanol 200mL, and water 150mL were charged in a 2L three-necked flask, and Pd (PPh3)4(11.5g, 10mmol) was added after the reaction system was purged with nitrogen. The reaction was heated under reflux for 6 hours to stop the reaction. Water was added to the system, and the mixture was allowed to stand for liquid separation, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and purified by column chromatography to obtain 23.0g of M1-1 as a white solid with a yield of about 86%.
(2) M1-1(26.8g, 0.1mol), sodium hydroxide (0.8g, 0.2mol) and 200mL of ethanol were put into a 1L three-necked flask, and the reaction was stopped by refluxing for 2 hours. The pH value is adjusted to 2-3 by 50 percent of dilute hydrochloric acid, stirred for half an hour and filtered by suction to obtain 24.9g of white solid M1-2 with the yield of about 98 percent.
(3) In a 1L three-necked flask, M1-2(25.4g, 0.1mol), 25g methanesulfonic acid and toluene are added in 200mL, stirred and heated, and reacted at 90-100 ℃ for 2 hours, then cooled to room temperature, 200mL distilled water is added, stirred for half an hour, and filtered by suction to obtain 21.2g white solid M1-3 with the yield of about 90%.
(4) M1-3(23.6g, 0.1mol) and 600mL of dichloromethane were added to a 2L three-necked flask, stirred, slowly added dropwise (40mL, 0.4mol, 30%) aqueous hydrogen peroxide, reacted at room temperature for 2 hours, and after completion of the reaction, 100mL of saturated aqueous sodium bicarbonate was added, followed by stirring, liquid separation and spin-drying to obtain 24.1g of a white solid M1-4, with a yield of about 90%.
(5) Under the protection of nitrogen, 1-bromo-2- (3-chlorophenoxy) benzene (28.4g, 0.1mol) and 400mL of THF were added into a 2L three-necked flask, cooled to-78 deg.C, n-butyllithium (100mL, 0.25mol) was slowly added dropwise under stirring for about 1 hour, the dropping funnel was flushed with 50mL of THF after dropping, and the temperature was maintained for 1 hour after dropping. In a low-temperature system at-78 ℃, a solution prepared from M1-4(26.8g, 0.1mol) and 60 ml of THF 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 dropping is finished, then the temperature is slowly raised to room temperature, the reaction is stirred at the room temperature for 1 hour, and the reaction is finished. Adjusting to neutrality, separating organic phase, extracting, drying, column chromatography, and spin-drying solvent to obtain 42.6g white solid M1-5 with yield about 90%.
(6) M1-5(47.3g, 0.1mol), concentrated hydrochloric acid 50mL, and glacial acetic acid 200mL were added to a 1L three-necked flask, stirred and heated, reacted at 100 ℃ for 4 hours, and cooled to room temperature. And adding 200ml of toluene and 100ml of water, standing, separating liquid, washing an organic phase to be neutral, drying, carrying out column chromatography, and spin-drying a solvent to obtain 38.7g of a white solid M1-6 with the yield of about 85%.
(7) M1-6(45.5g, 0.1mol) and 200mL of dichloromethane are added into a 1L three-necked flask, stirring is started, the temperature is controlled at 0-5 ℃, bromine (1.6g, 0.1mol) is added, and reaction is carried out for 3 hours at 0-5 ℃. The solution was neutralized, the organic phase was separated, dried and the solvent was evaporated under reduced pressure to give 48.1g of M1-7 as a white solid with a yield of about 90%.
(8) M1-7(53.4g, 0.1mol), 2-nitrobenzene-4, 4,5, 5-tetramethyl-1, 3, 2-dioxaborane (24.9g, 0.1mol), sodium carbonate (26.5g,0.25mol), toluene 200mL, ethanol 200mL, and water 150mL were charged in a 2L three-necked flask, and after the reaction system was purged with nitrogen, 0.1g of Pd2(dba)3, 0.05g X-phos was added. The reaction was heated under reflux for 6 hours to stop the reaction. Water was added to the system, and the mixture was allowed to stand for liquid separation, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and purified by toluene column chromatography to obtain 46g of white solid M1-8 with a yield of about 80%.
(9) M1-8(57.5g, 0.1mol), triphenylphosphine 65g and 200mL of o-dichlorobenzene were added to a 2L three-necked flask, and the mixture was stirred and heated at 178 ℃ and 182 ℃ for reaction for 3 hours to terminate the reaction. The solvent was evaporated off, subjected to column chromatography and evaporated to dryness under reduced pressure to give 42.3g of M1-9 as a white solid with a yield of about 78%.
(10) Under the protection of nitrogen, a 2L three-mouth bottle is stirred with magnetic force, M1-9(54.3g, 0.1mol), bromobenzene (15.7g, 0.1mol), copper powder (0.6g, 0.01mol), 1, 10-phenanthroline (2.0g, 0.01mol), potassium carbonate (20.7g, 0.15mol) and DMF500ml are sequentially added after nitrogen replacement. Heating to 125-130 ℃ under the protection of nitrogen for 8 hours, and finishing the reaction. Cooling, adding water, and filtering. The solid product was washed with water, filtered, dried and purified by column chromatography to give 49.5g of M1 as a white solid with a yield of about 80%.
Product MS [ M + H [ ]]+: 619; elemental analysis (C)39H22ClNO3S): theoretical value C: 75.54%, H: 3.58%, N: 2.26 percent; found value C: 75.66%, H: 3.70%, N: 2.08 percent
Synthesis of intermediates M2-M13
During preparation, corresponding raw materials are replaced, a proper material ratio is selected, other raw materials and steps are the same as those of the intermediate M1, and the intermediates M2-M13 can be obtained.
Figure BDA0003565809650000171
Figure BDA0003565809650000181
EXAMPLE 1 Synthesis of Compound I-4
Figure BDA0003565809650000182
The synthetic route is as follows:
Figure BDA0003565809650000183
the preparation process comprises the following steps: respectively adding M1(61.9g, 0.1mol), (4-phenylquinazolin-2-yl) boric acid (25g, 0.1mol), sodium carbonate (15.9g,0.15mol), toluene 250mL, ethanol 150mL and water 100mL into a 1L three-neck flask provided with a condenser, a magneton and a thermometer, replacing the reaction system with nitrogen for protection, adding Pd (PPh3)4(11.5g, 10mmol), magnetically stirring and heating to reflux reaction (the temperature in the system is 70-80 ℃) for 3 hours, and stopping 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 62.3g of product I-4 is obtained through filtration, and the yield is 79%.
Product MS [ M + H [ ]]+: 789; elemental analysis (C)53H31N3O3S): theoretical value C: 80.59%, H: 3.96%, N: 5.32 percent; actual value C: 80.77%, H: 3.85%, N: 5.50 percent.
EXAMPLE 2 Synthesis of Compound I-9
Figure BDA0003565809650000191
The synthetic route is as follows:
Figure BDA0003565809650000192
substituting M2 for M1, (5- (4- (tert-butyl) phenyl) -1,3, 4-oxadiazol-2-yl) boronic acid for (4-phenylquinazolin-2-yl) boronic acid the appropriate material ratios were chosen and the other starting materials and procedures were the same as in example 1 to give 57.3g of product I-9 in 73% yield.
Product MS [ M + H [ ]]+: 785; elemental analysis (C)51H35N3O4S): theoretical value C: 77.94%, H: 4.49%, N: 5.35 percent; actual value C: 77.77%, H: 4.65%, N: 5.50 percent
EXAMPLE 3 Synthesis of Compound I-22
Figure BDA0003565809650000193
The synthetic route is as follows:
Figure BDA0003565809650000201
using M3 instead of M1, (4- (5-phenyl-1, 3, 4-oxadiazol-2-yl) phenyl) boronic acid instead of (4-phenylquinazolin-2-yl) boronic acid, the appropriate material ratios were chosen and the other starting materials and procedures were the same as in example 1 to give 56.3g of product I-22 in 70% yield.
Product MS [ M + H [ ]]+: 805; elemental analysis (C)53H31N3O4S): theoretical value C: 78.99%, H: 3.88%, N: 5.21 percent; actual value C: 78.80%, H: 3.75%, N: 5.15 percent
EXAMPLE 4 Synthesis of Compound I-32
Figure BDA0003565809650000202
The synthetic route is as follows:
Figure BDA0003565809650000203
using M4 instead of M1 and naphtho [1,2-d ] thiazol-2-yl boronic acid instead of (4-phenylquinazolin-2-yl) boronic acid, the other raw materials and procedures were the same as in example 1, selecting the appropriate material ratio, to obtain 59.1g of product I-32 with a yield of 77%.
Product MS [ M + H [ ]]+: 768; elemental analysis (C)50H28N2O3S2): theoretical value C: 78.10%, H: 3.67%, N: 3.64 percent; actual value C: 78.25%, H: 3.49%, N: 3.48 percent.
EXAMPLE 5 Synthesis of Compound I-81
Figure BDA0003565809650000204
The synthetic route is as follows:
Figure BDA0003565809650000211
substituting M1 with M5 and substituting (4-phenylquinazolin-2-yl) boronic acid with naphtho [1,2-d ] thiazol-2-yl boronic acid, choosing appropriate ratios of materials and the other starting materials and procedures were the same as in example 1, to give 77.9g of product I-81 with a yield of 82%.
Product MS [ M + H [ ]]+: 951; elemental analysis (C)61H33N3O3S3): theoretical value C: 76.95%, H: 3.49%, N: 4.41 percent; actual value C: 76.77%, H: 3.61%, N: 4.55 percent.
EXAMPLE 6 Synthesis of Compound I-91
Figure BDA0003565809650000212
The synthetic route is as follows:
Figure BDA0003565809650000213
using M6 instead of M1, (5-phenyl-1, 3, 4-oxadiazol-2-yl) boronic acid instead of (4-phenylquinazolin-2-yl) boronic acid, the other starting materials and procedures were the same as in example 1, selecting the appropriate material ratios, to give 66.3g of product I-91 with a yield of 76%.
Product MS [ M + H [ ]]+: 873; elemental analysis (C)55H31N5O5S): theoretical value C: 75.59%, H: 3.58%, N: 8.01 percent; actual value C: 75.65%, H: 3.40%, N: 8.18 percent.
EXAMPLE 7 Synthesis of Compound I-97
Figure BDA0003565809650000221
The synthetic route is as follows:
Figure BDA0003565809650000222
using M7 instead of M1 and phenanthro [9,10-d ] oxazol-2-ylboronic acid instead of (4-phenylquinazolin-2-yl) boronic acid, the other starting materials and procedures were the same as in example 1, selecting the appropriate material ratios, to give 77.3g of product I-97 with a yield of 72%.
Product MS [ M + H [ ]]+: 1019; elemental analysis (C)69H37N3O5S): theoretical value C: 81.24%, H: 3.66%, N: 4.12 percent; actual value C: 81.40%, H: 3.81%, N: 4.25 percent.
EXAMPLE 8 Synthesis of Compound I-114
Figure BDA0003565809650000223
The synthetic route is as follows:
Figure BDA0003565809650000224
the preparation process comprises the following steps: m8(69.7g, 0.1mol), phenanthrene [9,10-d ] oxazol-2-yl boric acid (26.3g, 0.1mol), sodium carbonate (15.9g,0.15mol), toluene 250mL, ethanol 150mL and water 100mL are respectively added into a 1L three-necked flask provided with a condenser tube, a thermometer and a magneton, Pd (PPh3)4(11.5g, 10mmol) is added after the reaction system is replaced and protected by nitrogen, stirring is started, the reaction is heated to reflux reaction (the temperature in the system is 70-80 ℃) for 3 hours, and the reaction is stopped. 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, 51.8g of the compound I-114-1 is obtained through filtration, and the yield is 62%.
To a 1L three-necked flask equipped with a condenser tube, a thermometer and a magneton, I-114-1(83.6g, 0.1mol), quinolin-6-ylboronic acid (17.3g, 0.1mol), cesium carbonate (39g, 0.12mol) and 400ml of dioxane were added in this order under nitrogen protection, and stirring was started. Tri-tert-butylphosphine (0.8g, 4mmol) and tris (dibenzylideneacetone) dipalladium (1.4g, 1.5mmol) were added to the reaction flask under nitrogen. Then heating to 85 ℃, keeping the temperature 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 73.8g of the product I-114 with a yield of 70.4%.
Product MS [ M + H [ ]]+: 929; elemental analysis (C)63H35N3O4S): theoretical value C: 81.36%, H: 3.79%, N: 4.52 percent; actual value C: 81.45%, H: 3.91%, N: 4.65 percent.
EXAMPLE 9 Synthesis of Compound I-118
Figure BDA0003565809650000231
The synthetic route is as follows:
Figure BDA0003565809650000232
m9 was used instead of M8, benzo [ f ] [1,10] phenanthroline-6-yl boronic acid was used instead of phenanthrene [9,10-d ] oxazol-2-yl boronic acid, the appropriate material ratios were chosen, the other raw materials and procedures were the same as in example 8, and 61.4g of compound I-118-1 was obtained first, with a yield of 72.5%. Then I-118-1 was used instead of I-114-1, (6-isopropylquinolin-2-yl) boronic acid was used instead of quinolin-6-ylboronic acid, giving 64.2g of product I-118, with a yield of 65.4%.
Product MS [ M + H [ ]]+: 929; elemental analysis (C)63H35N3O4S): theoretical value C: 81.85%, H: 4.31%, N: 5.70 percent; actual value C: 81.75%, H: 3.25%, N: 5.85 percent.
EXAMPLE 10 Synthesis of Compound I-134
Figure BDA0003565809650000233
The synthetic route is as follows:
Figure BDA0003565809650000241
m10 was used instead of M8, benzo [ f ] [1,10] phenanthroline-6-yl boronic acid was used instead of phenanthrene [9,10-d ] oxazol-2-yl boronic acid, the appropriate material ratios were chosen, the other raw materials and procedures were the same as in example 8, 56.4g of compound I-134-1 was obtained, yield 74%. I-134-1 was then used instead of I-114-1, naphtho [2,3-d ] oxazol-2-ylboronic acid instead of quinolin-6-ylboronic acid, giving 67.2g of product I-134 with a yield of 75%.
Product MS [ M + H [ ]]+: 896; elemental analysis (C)58H32N4O5S): theoretical value C: 77.67%, H: 3.60%, N: 6.25 percent; actual value C: 77.81%, H: 3.75%, N: 6.38 percent.
EXAMPLE 11 Synthesis of Compound I-86
Figure BDA0003565809650000242
The synthetic route is as follows:
Figure BDA0003565809650000243
substituting M1 with M11 and substituting (4-phenylquinazolin-2-yl) boronic acid with naphtho [1,2-d ] thiazol-2-yl boronic acid, selecting appropriate ratios of materials and the other starting materials and procedures were the same as in example 1, to give 76g of product I-86 in 80% yield.
Product MS [ M + H [ ]]+: 951; elemental analysis (C)61H33N3O3S3): theoretical value C: 76.95%, H: 3.49%, N: 4.41 percent; actual value C: 7678%, H: 3.60%, N: 4.58 percent.
EXAMPLE 12 Synthesis of Compounds I-89
Figure BDA0003565809650000244
The synthetic route is as follows:
Figure BDA0003565809650000251
using M12 instead of M1, (5-phenyl-1, 3, 4-oxadiazol-2-yl) boronic acid instead of (4-phenylquinazolin-2-yl) boronic acid, the other starting materials and procedures were the same as in example 1, selecting the appropriate material ratios, 64.6g of product I-89 were obtained with a yield of 74%.
Product MS [ M + H [ ]]+: 873, a lubricant; elemental analysis (C)55H31N5O5S): theoretical value C: 75.59%, H: 3.58%, N: 8.01 percent; actual value C: 75.75%, H: 3.45%, N: 8.15 percent.
EXAMPLE 13 Synthesis of Compounds I-94
Figure BDA0003565809650000252
The synthetic route is as follows:
Figure BDA0003565809650000253
using M13 instead of M1 and naphtho [2,3-d ] oxazol-2-ylboronic acid instead of (4-phenylquinazolin-2-yl) boronic acid, the other materials and procedures were the same as in example 1, selecting the appropriate material ratios, to give 74.4g of product I-89, in 81% yield.
Product MS [ M + H [ ]]+: 919; elemental analysis (C)61H33N3O5S): theoretical value C: 79.64%, H: 3.62%, N: 4.57 percent; actual value C: 79.80%, H: 3.79%, N: 4.65 percent.
According to the synthetic schemes of the above examples 1 to 13, other compounds among the representative compounds I-1 to I-135 in the present invention can be synthesized by simply replacing the corresponding starting materials without changing any substantial operation.
Example 14
The embodiment provides a group of OLED blue light fluorescent devices, and the device structure is as follows: ITO/HATCN (1nm)/HT01(40nm)/NPB (30nm)/EML (30 nm)/any of the compounds (30nm)/LiF (1nm)/Al provided in examples 1 to 13, the preparation process comprising:
(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 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, evaporating and plating a layer of NPB (N-propyl bromide) on the hole injection layer film to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 30 nm; wherein the structural formulas of HATCN, HT01 and NPB are as follows:
Figure BDA0003565809650000261
(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 ADN is adjusted to be 0.1nm/s, the concentration of the dye material BD01 is adjusted to be 5%, and the total thickness of the evaporation film is 30nm by using a multi-source co-evaporation method; the structural formulas of ADN and BD01 are as follows:
Figure BDA0003565809650000262
(4) vacuum evaporation is carried out on the electron transport layer material of the device on the luminescent layer, and any compound provided in the embodiment 1 to the embodiment 13 is taken as the electron transport material of the electron transport layer of the device for evaporation, the evaporation rate is 0.1nm/s, and the total thickness of the evaporation film is 30 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; respectively obtaining a series of OLED-1-OLED-13 devices provided by the invention.
According to the same procedure as above, only the electron transporting material in the step (4) was replaced with comparative compound D1, the structural formula of which is shown below, to obtain comparative example device OLED-14.
Figure BDA0003565809650000271
The performance of the obtained devices OLED-1 to OLED-14 is detected, and the detection result is shown in Table 1.
Table 1:
Figure BDA0003565809650000272
it can be seen from the results in table 1 that, on the basis of the completely same device structure scheme, the organic compound represented by formula (I) provided by the present invention is used as an electron transport material to be compared in parallel with the comparative compound D-1, and the organic compound represented by formula (I) provided by the present invention is used as an electron transport layer material, so that the prepared device has high current efficiency, and under the condition of the same brightness, the operating voltage is significantly lower than that of the comparative device, and the lifetime is prolonged. The applicant believes that the stability of the compound is improved and the electron mobility is improved due to the fact that the aromatic group containing the five-membered heterocycle and having strong electron-withdrawing capability is introduced into the molecular structure of the compound, so that the compound is beneficial to injection balance of carriers in a functional layer in an applied OLED device, and finally the service life and the luminous efficiency of the device are improved.
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 (10)

1. An organic compound having the structure shown in formula (i):
Figure FDA0003565809640000011
in the general formula (I), X is selected from O, S, Se and NRX1、CRX2RX3、PRX4Or SiRX5RX6；
RX1、RX2、RX3、RX4、RX5And RX6Each independently selected from halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 straight chain or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-one of a C30 aryloxy, a substituted or unsubstituted C3-C30 heteroaryloxy, a substituted or unsubstituted C6-C60 aryl, a substituted or unsubstituted C3-C60 heteroaryl; rX2And RX3Can be connected in a ring between RX5And RX6Can be connected into a ring;
r is selected from one of substituted or unsubstituted C1-C20 straight chain or branched chain alkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
R1、R2、R3and R4Each independently represents a substituent group ranging from mono-substitution to the maximum allowable number, R1、R2、R3And R4Each independently selected from one of hydrogen, deuterium, halogen, amino, substituted or unsubstituted C1-C20 straight chain or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroaryl amino, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C5-C60 heteroaryl with electron withdrawing property;
and R is1、R2、R3And R4At least one of the aryl groups is a substituted or unsubstituted heteroaryl group with electron-withdrawing property of C5-C60, the heteroaryl group contains at least one heteroatom selected from N atom, S atom or O atom, and the aromatic group is connected with a mother nucleus shown in a formula (I) through a C atom;
r is as defined above1、R2、R3、R4、R、RX1、RX2、RX3、RX4、RX5And RX6The substituted substituent is respectively and independently selected from one or a combination of two of deuterium, halogen, C1-C20 straight-chain or branched-chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, nitro, cyano, amino, hydroxyl, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl and C3-C60 heteroaryl.
2. An organic light-emitting material according to claim 1, wherein X is selected from O, S or Se;
further, X is selected from O or S.
3. The organic light-emitting material of claim 1, wherein R is selected from substituted or unsubstituted aryl groups of C6-C30, and the substituent substituted on R is selected from one or a combination of two of deuterium, fluorine, cyano, amino, C1-C10 linear or branched alkyl groups, C3-C10 cycloalkyl groups, C1-C10 alkoxy groups, C6-C30 aryloxy groups, C3-C30 heteroaryloxy groups, C6-C60 aryl groups, and C3-C60 heteroaryl groups;
further, R is selected from substituted or unsubstituted phenyl.
4. An organic light-emitting material according to any one of claims 1 to 3, wherein R is1、R2、R3And R4At least one of the aryl is substituted or unsubstituted C5-C60 heteroaryl with electron withdrawing property, and the heteroaryl is selected from at least one or the combination of two of the following groups: a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted 1, 10-phenanthrolinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted benzopyrazinyl group, a substituted or unsubstituted s-triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group;
the substituted substituent on the heteroaryl is 1-4, and the substituted substituent on the heteroaryl is respectively and independently selected from one or a combination of two of C1-C20 straight-chain or branched-chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, nitro, cyano, amino, hydroxyl, C1-C20 alkyl silicon base, C1-C20 alkyl amino, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl and C3-C60 heteroaryl;
further, said R1、R2、R3And R4At least one selected from the group consisting of a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzopyrazinyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted 1, 10-phenanthrolinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted s-triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, and a substituted or unsubstituted pyrimidyl group; the substituted substituent on the heteroaryl is 1-3, and is respectively and independently selected from one or a combination of two of methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, phenyl, biphenyl, quinazolinyl, benzopyrazinyl, triazolyl, oxadiazolyl, benzo, naphtho, benzimidazolyl, naphthyl, pyridyl, pyrido, pyrrolyl, pyrrolo, imidazolyl, imidazo, pyrazolyl, pyrazolo, diazinyl, diazino, 1, 10-phenanthroline, s-triazinyl, fluorenyl, oxyfluorenyl, sulfenyl, quinolyl, isoquinolyl and carbazolyl.
5. An organic light-emitting material according to any one of claims 1 to 3, wherein R is1、R2、R3And R4At least one of the aryl is substituted or unsubstituted C5-C60 heteroaryl with electron withdrawing property, and the heteroaryl is selected from one of the following groups:
Figure FDA0003565809640000021
Figure FDA0003565809640000031
Figure FDA0003565809640000041
Figure FDA0003565809640000051
wherein the dotted line represents the substituted bit.
6. An organic light-emitting material according to claim 1, wherein the organic light-emitting material is selected from the following compounds:
Figure FDA0003565809640000052
Figure FDA0003565809640000061
Figure FDA0003565809640000071
Figure FDA0003565809640000081
Figure FDA0003565809640000091
Figure FDA0003565809640000101
Figure FDA0003565809640000111
7. use of the organic light emitting material according to any one of claims 1 to 6 as a functional material in an organic electronic device comprising an organic electroluminescent device, an optical sensor, a solar cell, a lighting 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 or electronic paper;
further, the organic luminescent material is applied to be used as an electron transport layer material in an organic electroluminescent device.
8. An organic electroluminescent device comprising an anode, a cathode and one or more light-emitting functional layers interposed between the anode and the cathode, wherein the light-emitting functional layers contain the organic light-emitting material according to any one of claims 1 to 6 therein;
further, the light emitting function layer comprises an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer, wherein the electron transport layer contains the organic light emitting material according to any one of claims 1 to 6;
furthermore, the thickness of the electron transmission layer is 10-50 nm, and the preferable thickness is 20-40 nm.
9. A display apparatus comprising the organic electroluminescent device according to claim 8.
10. A lighting device comprising the organic electroluminescent device according to claim 8.
CN202210306718.8A 2022-03-25 2022-03-25 Organic compound and application thereof Pending CN114605434A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116120277A (en) * 2023-03-03 2023-05-16 陕西师范大学 Synthesis method of 10H-benzo [ b ] indeno [2,1-d ] thiophene-10-ketone compound

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116120277A (en) * 2023-03-03 2023-05-16 陕西师范大学 Synthesis method of 10H-benzo [ b ] indeno [2,1-d ] thiophene-10-ketone compound
CN116120277B (en) * 2023-03-03 2024-04-05 陕西师范大学 Synthesis method of 10H-benzo [ b ] indeno [2,1-d ] thiophene-10-ketone compound

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