CN112778312B - Organic material containing indoloquinazolinedione heterocyclic structure and application thereof - Google Patents

Organic material containing indoloquinazolinedione heterocyclic structure and application thereof Download PDF

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CN112778312B
CN112778312B CN202011578535.9A CN202011578535A CN112778312B CN 112778312 B CN112778312 B CN 112778312B CN 202011578535 A CN202011578535 A CN 202011578535A CN 112778312 B CN112778312 B CN 112778312B
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范洪涛
梁现丽
杭德余
段陆萌
曹占广
班全志
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Beijing Yanhua Jilian Optoelectronic Technology Co ltd
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    • 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
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Abstract

The invention relates to the technical field of organic electroluminescent display, and particularly discloses an organic material containing an indoloquinazolinedione heterocyclic structure, and also discloses an application of the organic material in an organic electroluminescent device. The organic material containing the indole quinazoline dione heterocyclic structure is shown as a general formula (I), can be applied to the field of organic electroluminescence and can be used as an electron transport material. The structural compound provided by the invention is applied to an OLED device, and the device has the advantages of low driving voltage and high luminous efficiency.

Description

Organic material containing indoloquinazolinedione heterocyclic structure and application thereof
Technical Field
The invention relates to the technical field of materials for organic electroluminescence, and particularly discloses a novel organic material containing an indoloquinazolinedione heterocyclic 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 a carrier under the action of an electric field when the carrier (an electron or a hole) is injected, thereby carrying out charge transport. The organic charge transport material is mainly used for transporting holes and is called a hole type transport material, and the organic charge transport material is mainly used for transporting electrons and is called an electron type transport material or 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 working 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 electronic transmission 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.
Specifically, in a first aspect, the present invention provides an organic material containing an indoloquinazolinedione heterocyclic structure, having a structure represented by general formula (i):
Figure BDA0002864153380000021
wherein:
R 1 ～R 8 optionally selected from H, halogen atom, linear or branched alkyl, cycloalkyl, amino, alkylamino, substituted or unsubstituted aromatic group containing benzene ring and/or aromatic heterocycle, substituted or unsubstituted aromatic group containing hetero atom and having electron withdrawing property, and R 1 ～R 8 At least one of which is a substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing properties and is linked to the parent nucleus represented by the general formula (I) through a C atom on the substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing properties; r 1 ～R 8 May be the same or different.
The halogen atom is F, cl, br or I.
Straight chain alkyl refers to the general formula C n H 2n+1 Straight chain alkyl of-including but not limited to methyl, ethyl, propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and the like.
Branched alkyl groups include, but are not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, and the like.
Cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like.
Alkylamino refers to a group in which at least one H on the amino group is substituted with an alkyl group.
The substituted or unsubstituted aromatic group containing a heteroatom optionally selected from the group consisting of N atom, S atom and O atom and having electron withdrawing property contains at least one heteroatom. The substituted or unsubstituted aromatic group containing heteroatoms and having electron withdrawing property can be monocyclic aromatic hydrocarbon or polycyclic aromatic hydrocarbon; the polycyclic aromatic hydrocarbon can be poly-benzene aliphatic hydrocarbon, biphenyl polycyclic aromatic hydrocarbon or polycyclic aromatic hydrocarbon. The substituted or unsubstituted aromatic group containing a heteroatom and having an electron-withdrawing property may contain no five-membered ring or at least one five-membered ring.
Preferably, the substituted or unsubstituted aromatic group containing a heteroatom and having an electron-withdrawing property contains a benzene ring and a five-membered ring, and contains at least one heteroatom, specifically, a N atom, an S atom or an O atom, and the heteroatom may be on the five-membered ring or on the benzene ring.
When the substituted or unsubstituted aromatic group containing a heteroatom and having an electron-withdrawing property contains two heteroatoms, the two heteroatoms may be the same or different. Specifically, the two heteroatoms are both N atoms, or both S atoms, or both O atoms, or both N atoms and S atoms, or both N atoms and O atoms, or both S atoms and O atoms. The two heteroatoms may be on the same five-membered ring, may be on two different five-membered rings, may be on the same benzene ring, may be on two different benzene rings, or may be one on the five-membered ring and the other on the benzene ring.
When the substituted or unsubstituted heteroatom-containing aromatic group having an electron-withdrawing property contains three heteroatoms, the three heteroatoms may be the same, any two of the heteroatoms may be the same, or may be different from each other. Specifically, the three heteroatoms are all N atoms, or all S atoms, or all O atoms, or two N atoms and the other S atom, or two N atoms and the other O atom, or two S atoms and the other N atom, or two S atoms and the other O atom, or two O atoms and the other N atom, or two O atoms and the other S atom, or N atom, S atom and O atom, respectively. The three heteroatoms may all be on the same five-membered ring, may all be on the same benzene ring, may be any two of the other on the same five-membered ring on another five-membered ring, may be any two of the other on the same five-membered ring on a benzene ring, may be any two of the other on the same benzene ring on a five-membered ring, may be any two of the other on the same benzene ring on another benzene ring, may be any two of the other on different five-membered rings on a benzene ring, may be any two of the other on different benzene rings on five-membered rings, may be on three different five-membered rings, or may be on three different benzene rings, respectively.
In a preferred embodiment of the present invention, the substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing property is a monocyclic aromatic hydrocarbon group or a polycyclic aromatic hydrocarbon group, the polycyclic aromatic hydrocarbon group is optionally selected from a polyphenylaliphatic hydrocarbon group, a biphenyl-type polycyclic aromatic hydrocarbon group, a fused ring aromatic hydrocarbon group, the number of heteroatoms contained is 1 to 6, and the heteroatoms are optionally selected from N, O, S.
As a preferred embodiment of the present invention, the substituted or unsubstituted aromatic group containing a hetero atom and having an electron-withdrawing property is selected from the group consisting of 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-phenanthroline group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrimidyl 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, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group;
the substituted substituents may be 1 to 5, said substituents being optionally selected from: alkyl, 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, thiofluorenyl, quinolyl, isoquinolyl, carbazolyl;
the hydrogen on the substituent may be further substituted with any of the following groups 1 to 3, respectively: alkyl, phenyl, benzo, naphthyl, naphtho, pyridyl, biphenyl, quinazolinyl, benzopyrazinyl, triazolyl, oxadiazolyl, benzimidazolyl, fluorenyl, oxyfluorenyl, and dibenzothiophenyl.
As a further preferred embodiment, in the general formula (I), the substituted or unsubstituted aromatic group containing a heteroatom and having an electron-withdrawing property is selected from the group consisting of a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl 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-o-phenanthroline 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, a substituted or unsubstituted pyrimidyl group;
wherein, the substituted substituent can be 1-3, and the substituent is selected from the following groups: c 1 ～C 5 Alkyl, phenyl, biphenyl, quinazolinyl, benzopyrazinyl, triazolyl, oxadiazolyl, benzo, naphtho, benzimidazolyl, naphthyl, pyridyl, 1, 10-phenanthrolino, pyrazino, s-triazinyl, fluorenyl, oxyfluorenyl, thiofluorenyl, quinolyl;
the hydrogen on the substituent may be further substituted with any of the following groups 1 to 2, respectively: c 1 ～C 5 Alkyl, phenyl, benzo, naphthyl, naphtho, pyridyl, biphenyl, fluorenyl, oxyfluorenyl, or thiofluorenyl.
As a further preferred embodiment, the substituted or unsubstituted heteroatom-containing aromatic group having electron withdrawing properties is selected from the group consisting of:
Figure BDA0002864153380000041
Figure BDA0002864153380000051
Figure BDA0002864153380000061
preferably, the substituted or unsubstituted heteroatom-containing aromatic group having electron withdrawing properties is selected from the group consisting of:
Figure BDA0002864153380000062
Figure BDA0002864153380000071
Figure BDA0002864153380000081
further preferably, the substituted or unsubstituted heteroatom-containing aromatic group having electron withdrawing properties is selected from the group consisting of:
Figure BDA0002864153380000082
wherein "- -" represents a substituted bit.
As a further preferred embodiment, said R 1 ～R 8 Any one of the groups is a substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing properties;
or, R 1 ～R 8 Any two of the groups are substituted or unsubstituted aromatic groups containing hetero atoms and having electron withdrawing properties, and the two groups are located on different benzene rings, or located on the same benzene ring, preferably located on different benzene rings; the two groups may be the same or different from each other.
As a further preferred embodiment, said R 1 ～R 8 Wherein, in addition to representing a substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing properties, the remaining radicals being selected from hydrogen atoms, radicalsAnd a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.
In a preferred embodiment of the present invention, R is 1 ～R 8 In, R 1 、R 6 Is a group other than a hydrogen atom; or, R 1 、R 7 Is a group other than a hydrogen atom; or, R 2 、R 6 Is a group other than a hydrogen atom; or, R 2 、R 7 Is a group other than a hydrogen atom; or, R 3 、R 6 Is a group other than a hydrogen atom; or, R 3 、R 7 Is a group other than a hydrogen atom; or, R 3 、R 8 Is a group other than a hydrogen atom; or, R 4 、R 6 Is a group other than a hydrogen atom; or, R 4 、R 7 Is a group other than a hydrogen atom; r 1 ～R 8 Wherein the others each represent a hydrogen atom.
Further preferably, R 1 ～R 8 In, R 1 、R 6 Is a group other than a hydrogen atom; or, R 2 、R 6 Is a group other than a hydrogen atom; or, R 2 、R 7 Is a group other than a hydrogen atom; or, R 3 、R 6 Is a group other than a hydrogen atom; or, R 3 、R 7 Is a group other than a hydrogen atom; or, R 4 、R 7 Is a group other than a hydrogen atom; r 1 ～R 8 Wherein the others each represent a hydrogen atom.
As a preferred embodiment of the present invention, the organic material is selected from compounds represented by the following structural formula:
Figure BDA0002864153380000091
Figure BDA0002864153380000101
Figure BDA0002864153380000111
in a second aspect, the invention provides an application of the organic material containing the indole quinazoline dione heterocyclic structure in preparation of an organic electroluminescent device.
Preferably, the organic material containing the indole quinazoline diketone heterocyclic ring 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 material of the electron transport layer contains the organic material containing the indole quinazoline diketone heterocyclic ring structure.
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) provided by the invention.
In a preferred embodiment, the thickness of the electron transport layer may be 10 to 50nm, preferably 20 to 40nm.
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 an indole quinazoline diketone heterocyclic structure, which is specifically shown as a general formula (I), wherein the indole quinazoline diketone heterocyclic structure is taken as a parent nucleus, the parent nucleus of the series of compounds has strong electron-withdrawing capability and good thermal stability, and the structure has proper HOMO and LUMO energy levels and Eg; the organic light emitting diode is connected with the electron-withdrawing group, so that the electron injection capability can be effectively enhanced, the electron transmission performance is improved, the organic light emitting diode can be well applied to an OLED device and used as an electron transmission material, and the photoelectric performance of the device can be effectively improved.
The organic material containing the indole quinazoline dione heterocyclic structure provided by the invention can be used as an electron transport material, has high electron transport performance, high film stability and proper molecular energy level, can be applied to the field of organic electroluminescence, and can effectively improve the photoelectric property of a device. Meanwhile, the organic light emitting diode has the advantages of good thermal stability, stability and high efficiency, and can be well applied to OLED devices. Therefore, the driving voltage can be reduced, the luminous efficiency of the device can be improved, and the method has important practical application value. The organic electroluminescent device made of the organic material has the characteristics of low driving voltage and high luminous efficiency. 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.
Synthesis of intermediates
Synthesis of intermediate M1
Figure BDA0002864153380000121
The synthetic route is as follows:
Figure BDA0002864153380000122
the specific operation steps are as follows:
in DMSO, I 2 (1.5 equiv.), cuI (0.3 equiv.), K 2 CO 3 (1 eq) 2-amino-5-chlorobenzamide was reacted with 1- (2-bromo-5-chlorophenyl) ethan-1-one at 100 ℃ for 6 hours to give intermediate M1 in 70% yield. (production method references: international Journal of Pharma Research and Health Sciences,2018 (6): 2865-68.
With reference to the literature, and with reference to the method of synthesis of intermediate M1, other desired intermediates M2 to M8 were synthesized.
EXAMPLE 1 Synthesis of Compound I-1
Figure BDA0002864153380000131
The synthetic route is as follows:
Figure BDA0002864153380000132
the preparation process comprises the following steps: A1L three-necked flask was taken, and stirred with magnetic force, after nitrogen substitution, M1 (31.6 g, 0.1mol), (4-phenylquinazolin-2-yl) boronic acid (50.0 g, 0.2mol), cesium carbonate (78g, 0.24mol) and dioxane (400 ml) were added in this order, and stirring was started. After nitrogen substitution was again carried out, (1.5g, 8mmol) tri-tert-butylphosphine and (2.7g, 3mmol) 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 51.9g of light yellow solid with the yield of about 79%.
Product MS (m/e): 656.20; elemental analysis (C) 43 H 24 N 6 O 2 ): theoretical value C:78.65%, H:3.68%, N:12.80 percent; measured value C:78.70%, H:3.73%, N:12.65 percent.
EXAMPLE 2 Synthesis of Compound I-13
Figure BDA0002864153380000133
The synthetic route is as follows:
Figure BDA0002864153380000134
the preparation process comprises the following steps: A1L three-necked flask was taken, and magnetic stirring was carried out, then M2 (31.6 g, 0.1mol), benzo [ d ] thiazol-2-ylboronic acid (35.8g, 0.2mol), cesium carbonate (78g, 0.24mol) and dioxane (400 ml) were sequentially added under nitrogen substitution, and stirring was carried out. After the nitrogen substitution, tri-tert-butylphosphine (1.5g, 8 mmol) and tris (dibenzylideneacetone) dipalladium (2.7g, 3 mmol) 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 34.4g of pale yellow solid with the yield of about 67%.
Product MS (m/e): 514.06; elemental analysis (C) 29 H 14 N 4 O 2 S 2 ): theoretical value C:67.69%, H:2.74%, N:10.89 percent; found value C:67.74%, H:2.79%, N:10.73 percent.
EXAMPLE 3 Synthesis of Compound I-22
Figure BDA0002864153380000141
The synthetic route is as follows:
Figure BDA0002864153380000142
the preparation process comprises the following steps: A1L three-necked flask was taken, and magnetic stirring was carried out, then, M3 (31.6 g, 0.1mol), (1-phenyl-1H-naphthalene [2,3-d ] imidazol-2-yl) boronic acid (57.6 g, 0.2mol), cesium carbonate (78g, 0.24mol) and dioxane (400 ml) were sequentially added after nitrogen substitution, and stirring was started. After nitrogen substitution was again carried out, (1.5g, 8mmol) tri-tert-butylphosphine and (2.7g, 3mmol) 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 47.6g of pale yellow solid with the yield of about 65%.
Product MS (m/e): 732.23; elemental analysis (C) 49 H 28 N 6 O 2 ): theoretical value C:80.31%, H:3.85%, N:11.47 percent; found value C:80.38%, H:3.90%, N:11.30 percent.
EXAMPLE 4 Synthesis of Compound I-36
Figure BDA0002864153380000143
The synthetic route is as follows:
Figure BDA0002864153380000151
the preparation process comprises the following steps: into a 1L three-necked flask, M4 (36.0g, 0.1mol), (9, 9-dimethyl-9H-fluoren-2-yl) boronic acid (23.8g, 0.1mol), sodium carbonate (15.9g, 0.15mol), toluene 150mL, ethanol 150mL, and water 150mL were charged, and after the reaction system was purged with nitrogen, pd (PPh) was added 3 ) 4 (11.5g, 10mmol). The reaction was heated under reflux (temperature in the system: about 78 ℃ C.) for 3 hours to stop the reaction. The solvent was evaporated, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered, column-chromatographed with petroleum ether/ethyl acetate (2.
A1L three-necked flask was taken, stirred with magnetic force, purged with nitrogen, and then sequentially added with I-36-1 (47.4 g, 0.1mol), (3, 5-bis (pyridin-4-yl) phenyl) boronic acid (27.6 g, 0.1mol), cesium carbonate (39g, 0.12mol) and dioxane 400ml, followed by stirring. After the nitrogen substitution 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 an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 54.9g of pale yellow solid with the yield of about 82%.
Product MS (m/e): 670.24; elemental analysis (C) 46 H 30 N 4 O 2 ): theoretical value C:82.37%, H:4.51%, N:8.35 percent; found value C:82.43%, H:4.55%, N:8.21 percent.
EXAMPLE 5 Synthesis of Compound I-39
Figure BDA0002864153380000152
The synthetic route is as follows:
Figure BDA0002864153380000161
the preparation process comprises the following steps: A1L three-necked flask was taken, stirred with magnetic force, and after nitrogen substitution, M2 (31.6 g, 0.1mol), (1, 10-phenanthroline-5-yl) boronic acid (44.8g, 0.2mol), cesium carbonate (78g, 0.24mol) and dioxane (400 ml) were sequentially added thereto, followed by stirring. After nitrogen substitution was again carried out, (1.5g, 8mmol) tri-tert-butylphosphine and (2.7g, 3mmol) 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 39.3g of light yellow solid with the yield of about 65%.
Product MS (m/e): 604.16; elemental analysis (C) 39 H 20 N 6 O 2 ): theoretical value C:77.47%, H:3.33%, N:13.90 percent; found value C:77.53%, H:3.39%, N:13.73 percent.
EXAMPLE 6 Synthesis of Compound I-43
Figure BDA0002864153380000162
The synthetic route is as follows:
Figure BDA0002864153380000163
the preparation process comprises the following steps: A1L three-necked flask was taken, stirred with magnetic force, purged with nitrogen, and then sequentially charged with M5 (31.6 g, 0.1mol), (4, 6-diphenyl-1, 3, 5-triazin-2-yl) boronic acid (55.4 g, 0.2mol), cesium carbonate (78g, 0.24mol) and dioxane 400ml, followed by stirring. After the nitrogen substitution, tri-tert-butylphosphine (1.5g, 8 mmol) and tris (dibenzylideneacetone) dipalladium (2.7g, 3 mmol) 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 39.3g pale yellow solid with yield about 80%.
Product MS (m/e): 710.22; elemental analysis (C) 45 H 26 N 8 O 2 ): theoretical value C:76.04%, H:3.69%, N:15.77 percent; measured value C:76.09%, H:3.55%, N:15.61 percent.
EXAMPLE 7 Synthesis of Compound I-50
Figure BDA0002864153380000171
The synthetic route is as follows:
Figure BDA0002864153380000172
the preparation process comprises the following steps: into a 1L three-necked flask, M6 (36.0 g, 0.1mol), (4- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) phenyl) boronic acid (35.3 g, 0.1mol), sodium carbonate (15.9 g, 0.15mol), toluene 150mL, ethanol 150mL, and water 150mL were charged, and Pd (PPh) was added after the reaction system was purged with nitrogen 3 ) 4 (11.5g, 10mmol). The reaction was heated under reflux (temperature in the system: about 78 ℃ C.) for 3 hours to stop the reaction. The solvent was evaporated off under reduced pressure, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered, subjected to column chromatography with petroleum ether/ethyl acetate (2Solid I-50-1, yield about 78%.
A1L three-necked flask was taken, and magnetic stirring was carried out, then, after nitrogen substitution, I-50-1 (58.9g, 0.1mol), 2-naphthylboronic acid (17.2g, 0.1mol), cesium carbonate (39g, 0.12mol) and dioxane (400 ml) were sequentially added thereto, and stirring was carried out. After the 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 an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 61.3g of pale yellow solid with the yield of about 90%.
Product MS (m/e): 681.22; elemental analysis (C) 47 H 27 N 5 O 2 ): theoretical value C:81.04%, H:3.99%, N:10.27 percent; measured value C:81.09%, H:4.06%, N:10.08 percent.
EXAMPLE 8 Synthesis of Compound I-54
Figure BDA0002864153380000181
The synthetic route is as follows:
Figure BDA0002864153380000182
the preparation process comprises the following steps: A1L three-necked flask was taken, and stirred by magnetic force, and after nitrogen substitution, M5 (31.6 g,0.1 mol), (4- (dibenzo [ b, d ] furan-3-yl) -6-phenyl-1, 3, 5-triazin-2-yl) boronic acid (73.4 g,0.2 mol), cesium carbonate (78g, 0.24mol) and dioxane (400 ml) were added in this order, followed by stirring. After nitrogen substitution was again carried out, (1.5g, 8mmol) tri-tert-butylphosphine and (2.7g, 3mmol) 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 66.8g of pale yellow solid with the yield of about 75%.
Product MS (m/e): 890.24; elemental analysis (C) 57 H 30 N 8 O 4 ): theoretical value C:76.85%, H:3.39%, N:12.58 percent; measured value C:76.89%, H:3.45%, N:12.42 percent.
EXAMPLE 9 Synthesis of Compound I-56
Figure BDA0002864153380000183
The synthetic route is as follows:
Figure BDA0002864153380000191
the preparation process comprises the following steps: A1L three-necked flask was charged with M7 (36.0g, 0.1mol), (4, 6-bis (quinolin-3-yl) -1,3, 5-triazin-2-yl) boronic acid (37.9g, 0.1mol), sodium carbonate (15.9g, 0.15mol), toluene 150mL, ethanol 150mL, and water 150mL, and the reaction system was purged with nitrogen and then protected with Pd (PPh) 3 ) 4 (11.5g, 10mmol). The reaction was heated under reflux (temperature in the system: about 78 ℃ C.) for 3 hours to stop the reaction. The solvent was evaporated, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered, column-chromatographed with petroleum ether/ethyl acetate (2.
A1L three-necked flask was taken, stirred with magnetic force, and then replaced with nitrogen, followed by sequentially adding I-56-1 (61.5g, 0.1mol), (4-cyclohexylphenyl) boronic acid (20.4g, 0.1mol), cesium carbonate (39g, 0.12mol), and dioxane 400ml, followed by stirring. After the nitrogen substitution 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 light yellow solid 62.1g with yield of about 84%.
Product MS (m/e): 739.27; elemental analysis (C) 48 H 33 N 7 O 2 ): theoretical value C:77.93%, H:4.50%, N:13.25 percent; found value C:77.99%, H:4.55%, N:13.08 percent.
EXAMPLE 10 Synthesis of Compound I-59
Figure BDA0002864153380000192
The synthetic route is as follows:
Figure BDA0002864153380000201
the preparation process comprises the following steps: into a 1L three-necked flask, M8 (36.0g, 0.1mol), (4, 6-diphenyl-1, 3, 5-triazin-2-yl) boronic acid (27.7g, 0.1mol), sodium carbonate (15.9g, 0.15mol), toluene (150 mL), ethanol (150 mL), and water (150 mL) were charged, and after the reaction system was purged with nitrogen, pd (PPh) 3 ) 4 (11.5g, 10mmol). The reaction was heated under reflux (temperature in the system: about 78 ℃ C.) for 3 hours to stop the reaction. The solvent was evaporated off, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered, column-chromatographed with petroleum ether/ethyl acetate (2).
A1L three-necked flask was taken, stirred with magnetic force, and then, after nitrogen substitution, I-59-1 (51.3g, 0.1mol), (4-phenylquinazolin-2-yl) boronic acid (25.0 g, 0.1mol), cesium carbonate (39g, 0.12mol) and dioxane (400 ml) were sequentially added thereto, followed by stirring. After the nitrogen substitution 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 56.0g pale yellow solid with yield about 82%.
Product MS (m/e): 683.21; elemental analysis (C) 44 H 25 N 7 O 2 ): theoretical value C:77.29%, H:3.69%, N:14.34 percent; found value C:77.35%, H:3.74%, N:14.18 percent.
According to the synthesis schemes of the above examples 1 to 10, other compounds in I-1 to I-60 can be synthesized by simply replacing the corresponding raw materials without changing any substantial operation.
Example 11
The embodiment provides a group of OLED blue light fluorescent devices, and the device structure is as follows: ITO/HATCN (1 nm)/HT 01 (40 nm)/NPB (20 nm)/EML (30 nm)/any of the compounds (40 nm)/LiF (1 nm)/Al provided in examples 1 to 10, the preparation process was:
(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 -3 Pa, 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 1nm; then evaporating a second hole injection layer HT01 at the evaporation rate of 0.1nm/s and the thickness of 40nm; 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 20nm; wherein the structural formulas of HATCN, HT01 and NPB are as follows:
Figure BDA0002864153380000211
(3) The method comprises the following steps of performing vacuum evaporation on an EML (electron emission layer) serving as a light emitting layer of a device on a hole transport layer, wherein the EML comprises a main material and a dye material, and adjusting the evaporation rate of the main material ADN to be 0.1nm/s, the concentration of the dye material BD01 to be 5% and the total evaporation film thickness to be 30nm by using a multi-source co-evaporation method; the structural formulas of ADN and BD01 are as follows:
Figure BDA0002864153380000212
(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 10 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 40nm;
(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 150nm; respectively 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 a comparative compound, the structural formula of which is shown below, to obtain a comparative example device OLED-11.
Figure BDA0002864153380000213
The performance of the obtained devices OLED-1-OLED-11 is detected, and the detection results are shown in Table 1.
TABLE 1
Figure BDA0002864153380000221
The results in table 1 show that the novel organic material of the present invention is used for organic electroluminescent devices, the current efficiency of the manufactured devices is high, the working voltage is obviously superior to that of the comparative devices under the condition of the same brightness, and the organic material 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 (10)

1. An organic material containing an indoloquinazolinedione heterocyclic structure, which is characterized by having a structure shown as a general formula (I):
Figure FDA0003883141040000011
wherein:
R 1 ～R 8 at least one of which is a substituted or unsubstituted heteroatom-containing aromatic group having electron withdrawing properties, the remaining groups being independently selected from hydrogen atoms, fluorenyl groups, dibenzofuranyl groups, dibenzothienyl groups, spirobifluorenyl groups, naphthyl groups, phenyl groups, biphenyl groups;
the substituted or unsubstituted heteroatom-containing aromatic group having electron withdrawing properties is selected from the group consisting of:
Figure FDA0003883141040000012
Figure FDA0003883141040000021
Figure FDA0003883141040000031
Figure FDA0003883141040000041
wherein "- -" represents a substituted bit.
2. The organic material according to claim 1, wherein the substituted or unsubstituted heteroatom-containing aromatic group having electron withdrawing properties is selected from the group consisting of:
Figure FDA0003883141040000042
Figure FDA0003883141040000051
3. the organic material according to claim 1, wherein the substituted or unsubstituted heteroatom-containing aromatic group having electron withdrawing properties is selected from the group consisting of:
Figure FDA0003883141040000052
Figure FDA0003883141040000061
4. the organic material according to any one of claims 1 to 3, wherein R is 1 ～R 8 Any one of the groups is a substituted or unsubstituted heteroatom-containing aromatic group having electron-withdrawing properties;
or, R 1 ～R 8 Any two groups are substituted or unsubstituted heteroatom-containing aromatic groups with electron-withdrawing property, and the two groups are positioned on different benzene rings or on the same benzene ring; the two groups may be the same or different from each other.
5. An organic material containing an indoloquinazolinedione heterocyclic structure, wherein the organic material is selected from compounds represented by the following structural formula:
Figure FDA0003883141040000062
Figure FDA0003883141040000071
Figure FDA0003883141040000081
6. use of the organic material containing an indoloquinazolinedione heterocyclic structure according to any of claims 1 to 5 for the preparation of organic electroluminescent devices.
7. The use according to claim 6, wherein the organic material containing the heterocyclic structure of indoloquinazolinedione is used as an electron transport material in an organic electroluminescent device.
8. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises an electron transport layer, and the material of the electron transport layer contains the organic material containing the indole quinazoline dione heterocyclic structure according to any one of claims 1 to 5.
9. A display device comprising the organic electroluminescent element according to claim 8.
10. A lighting device characterized by comprising the organic electroluminescent element according to claim 8.
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