CN112961140B - Naphthoquinone heterocyclic compound and application thereof - Google Patents

Naphthoquinone heterocyclic compound and application thereof Download PDF

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CN112961140B
CN112961140B CN202110169880.5A CN202110169880A CN112961140B CN 112961140 B CN112961140 B CN 112961140B CN 202110169880 A CN202110169880 A CN 202110169880A CN 112961140 B CN112961140 B CN 112961140B
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温洁
陈婷
段陆萌
梁现丽
杭德余
曹占广
班全志
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Beijing Yunji Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • H—ELECTRICITY
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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    • Y02E10/00—Energy generation through renewable energy sources
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Abstract

The invention relates to the technical field of organic electroluminescent display, and particularly discloses an organic material of a naphthoquinone heterocyclic compound, and also discloses an application of the organic material in an organic electroluminescent device. The naphthoquinone heterocyclic compound provided by the invention 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, can reduce the driving voltage of the device and improve the luminous efficiency of the device.

Description

Naphthoquinone heterocyclic compound and application thereof
Technical Field
The invention relates to the technical field of materials for organic electroluminescence, and particularly discloses a novel compound containing a naphthoquinone heterocyclic structure, and also discloses application of the compound in an organic electroluminescent device.
Background
The application of the organic electroluminescent (OLED) material in the fields of information display materials, organic optoelectronic materials and the like has great research value and good application prospect. With the development of multimedia information technology, the requirements for the performance of flat panel display devices are higher and higher. The main display technologies at present are plasma display devices, field emission display devices, and organic electroluminescent display devices (OLEDs). Compared with liquid crystal display devices, OLEDs do not need backlight sources, have wider viewing angles and low power consumption, and have response speed 1000 times that of the liquid crystal display devices, so the OLEDs have wider application prospects.
Since the first reports of high efficiency Organic Light Emitting Diodes (OLEDs), 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 working voltage and serious power consumption of the device; part of the electron transport materials such as LG201 are not high in triplet energy level, 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, are prone to crystallization, resulting in reduced lifetimes. These problems with electron transport materials are bottlenecks that affect the development of organic electroluminescent display devices. Therefore, the development of new electron transport materials with better performance has important practical application value.
Disclosure of Invention
The invention aims to develop an electron transport material of an organic electroluminescent device, which is applied to an OLED device, can reduce driving voltage and improve the luminous efficiency of the device.
Specifically, in a first aspect, the present invention provides a naphthoquinone heterocyclic compound having a structure represented by general formula (i):
Figure BDA0002938659720000021
wherein:
R 1 ～R 8 is optionally selected from H, halogen atom, linear or branched alkyl, cycloalkyl, substituted or unsubstituted C 6 ～C 40 A monocyclic or polycyclic aromatic hydrocarbon group of (A), and R 1 ～R 8 At least one of which is substituted or unsubstituted C 6 ～C 40 Monocyclic aromatic hydrocarbon group or polycyclic aromatic hydrocarbon group of (a).
The halogen atom is F, cl, br or I.
Straight chain alkyl refers to the general formula C n H 2n+1 Straight chain alkyl of (E) -including but not limited to methyl, ethyl, propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and the like. Preferably, n is a straight chain alkyl group of 1 to 5.
Branched chain-containing alkyl groups include, but are not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, and the like. Branched alkyl groups having a carbon number of 1 to 5 are preferred.
Cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like. Cycloalkyl groups having 3 to 6 carbon atoms are preferred.
C 6 ～C 40 The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (1), wherein the monocyclic aromatic hydrocarbon group is preferably an aromatic hydrocarbon group having one benzene ring; the polycyclic aromatic hydrocarbon group is polyphenyl aliphatic hydrocarbon group, biphenyl and biphenyl type polycyclic aromatic hydrocarbon group, spirobifluorene group or condensed ring aromatic hydrocarbon group.
Polycyclic aromatic hydrocarbon groups include, but are not limited to, groups comprising biphenyl, terphenyl, naphthalene, acenaphthene, dihydroacenaphthene, fluorene, spirobifluorene, phenanthrene, pyrene, fluoranthene, chrysene, benzo (a) anthracene, benzofluoranthene, triphenylene, benzopyrene, perylene, indenofluoranthene.
As a preferred embodiment of the present invention, said substituted or unsubstituted C 6 ～C 40 The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group in the polycyclic aromatic hydrocarbon group is any one of polyphenyl aliphatic hydrocarbon group, biphenyl type polycyclic aromatic hydrocarbon group, spirobifluorene group and condensed ring aromatic hydrocarbon group; said substituted C 6 ～C 40 The substituents of the monocyclic or polycyclic aromatic hydrocarbon group of (a) are optionally selected from: halogen, straight-chain or branched-chain-containing alkyl, cycloalkyl, polycyclic aryl, polycyclic aryloaryl, monocyclic aryl, monocyclic aryloaryl, heterocyclic aryloaryl, and the number of the substituent groups is selected from an integer of 1-7.
The polycyclic aryl groups can be biphenyl, phenanthryl, fluorenyl, anthracyl, fluoranthenyl, triphenylenyl, naphthyl, and the like.
The polycyclic arylo group may be phenanthro, anthraco, fluorantheno, triphenylo, naphtho, or the like.
Monocyclic aryl is preferably phenyl.
The monocyclic aryl-o group is preferably a benzo group.
The heterocyclic aryl group is a group having an aromatic heterocyclic ring, and may be benzothienyl, benzofuranyl, pyridyl, pyrimidyl, thiazolyl, or the like.
The heterocycloaryl group may be benzothieno, benzofuro, or the like.
As a preferred embodiment of the present invention, said substituted or unsubstituted C 6 ～C 40 The monocyclic aromatic hydrocarbon group or polycyclic aromatic hydrocarbon group of (a) is optionally selected from: a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted benzo (a) anthracenyl group, a substituted or unsubstituted benzo (b) fluoranthenyl group, a substituted or unsubstituted benzo (k) fluoranthenyl group, a substituted or unsubstituted benzo (a) pyrenyl group, a substituted or unsubstituted indenofluoranthenyl group, a substituted or unsubstituted perylenyl group; the substituted substituent can be 1-3, and the substituent is selected from halogen and C 1-5 Linear or branched alkyl, C 3-8 Cycloalkyl, monocyclic aryl, monocyclic arylo, polycyclic aryl, polycyclic arylo of (a); the hydrogen on the substituent may be further substituted with 1 to 2 of the following optional substituents, respectively: c 1-5 Of a straight chain orAlkyl containing a branch, C 3-8 Cycloalkyl, phenyl.
As a preferred embodiment of the present invention, said substituted or unsubstituted C 6 ～C 40 The monocyclic aromatic hydrocarbon group or polycyclic aromatic hydrocarbon group of (a) is optionally selected from: a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted fluoranthyl group, a substituted or unsubstituted indenofluoranthyl group, a substituted or unsubstituted perylenyl group; the substituted substituent can be 1-3, and the substituent is selected from halogen and C 1-5 Linear or branched alkyl, C 3-8 Cycloalkyl, phenyl, biphenyl, naphthyl, naphtho, phenanthryl, benzo, triphenylene, fluoranthenyl; the hydrogen on the substituent may be further substituted with 1 to 2 of the following optional substituents, respectively: c 1-5 Linear or branched alkyl, C 3-8 Cycloalkyl, phenyl.
As a preferred embodiment of the present invention, said substituted or unsubstituted C 6 ～C 40 The monocyclic aromatic hydrocarbon group or polycyclic aromatic hydrocarbon group of (a) is optionally selected from: substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted indenopfluoranthenyl, substituted or unsubstituted perylenyl; the substituted substituent can be 1-2, and the substituent is selected from C 1-5 Linear or branched alkyl, C 3-6 Cycloalkyl, phenyl, biphenyl, naphthyl, phenanthryl, benzo, triphenylene, naphtho, fluoranthenyl.
As a preferred embodiment of the present invention, said substituted or unsubstituted C 6 ～C 40 Monocyclic or polycyclic aromatic hydrocarbon group of (A) anySelected from the following groups:
Figure BDA0002938659720000031
Figure BDA0002938659720000041
Figure BDA0002938659720000051
wherein
Figure BDA0002938659720000052
Represents the linking position of the substituent to the parent nucleus.
As a preferred embodiment of the present invention, in the general formula (I), R is as defined above 1 ～R 8 Except that represents substituted or unsubstituted C 6 ～C 40 The remainder of the monocyclic aromatic hydrocarbon group or polycyclic aromatic hydrocarbon group(s) is a H atom.
The R is 1 ～R 8 In which any one group is said substituted or unsubstituted C 6 ～C 40 Monocyclic aromatic hydrocarbon group or polycyclic aromatic hydrocarbon group.
Or, said R 1 ～R 8 Wherein two are said substituted or unsubstituted C 6 ～C 40 The two groups are located on different benzene rings, or on the same benzene ring; the two groups may be the same or different from each other.
As a preferred embodiment of the present invention, the compound represented by the general formula (I) is preferably selected from compounds represented by the following structural formulae:
Figure BDA0002938659720000053
Figure BDA0002938659720000061
Figure BDA0002938659720000071
in a second aspect, the invention provides an application of the naphthoquinone heterocyclic compound in preparation of an organic electroluminescent device.
Preferably, the naphthoquinone heterocyclic compound 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 naphthoquinone heterocyclic compound.
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 naphthoquinone heterocyclic compound, the parent nucleus of the series of compounds has stronger electron withdrawing capability, and can be used as an electron transmission material by being connected with a neutral group; meanwhile, the organic light emitting diode has good thermal stability and can be well applied to OLED devices. The organic compound is represented by a general formula (I), and can be applied to OLED devices and used as an OLED electron transmission material, so that the purposes of reducing the driving voltage of the devices and improving the luminous efficiency can be achieved.
The compound provided by the invention takes a naphthoquinone heterocyclic structure as a parent nucleus, the parent nucleus structure has strong electron-withdrawing capability and good thermal stability, and the structure has proper HOMO and LUMO energy levels and Eg; we have found that this is further achieved by introducing a neutral group R into the parent nucleus structure 1 ～R 8 The electron transport performance of the material can be improved by changing the stacking mode among molecules.
In conclusion, the novel OLED material provided by the invention takes a naphthoquinone heterocyclic structure as a parent nucleus, the parent nucleus structure has strong electron withdrawing capability, and a neutral group is introduced into the parent structure to obtain the novel OLED material. The material has good electron transport performance, good film stability and proper molecular energy level, can be applied to the field of organic electroluminescence, can be used as an electron transport material, can effectively improve the photoelectric performance of a device, and can be applied to 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 given to illustrate the present invention and 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 realize the preparation, 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, etc., which is 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 M1 to M15
Synthesis of intermediates M1 and M2
Figure BDA0002938659720000081
The synthetic route is as follows:
Figure BDA0002938659720000082
the specific operation steps are as follows:
(1) To a 2L three-necked flask equipped with mechanical stirring, dichloromethane (200 mL) and aluminum trichloride (29.3 g, 0.22mol) were added, stirring was turned on, after which 4-bromophthalic anhydride (22.6 g,0.1 mol) was dissolved in dichloromethane (150 mL) and added to the three-necked flask, and after stirring at room temperature (25-30 ℃ C.) for 30 minutes, benzothiophene (13.4 g,0.1 mol) was added over 1 hour, and then the reaction mixture was stirred at room temperature (25-30 ℃ C.) for 3 hours. After completion of the reaction, the reaction mixture was carefully quenched with hydrochloric acid (0.2M, 1L), extracted with dichloromethane, washed with aqueous NaOH (0.1M, 3X 200 mL), the aqueous layer was extracted with dichloromethane, and the solvent was distilled off under reduced pressure to obtain a solid which was directly charged into the next step.
The solid obtained above, nitrobenzene (200 mL) and phosphorus pentachloride (31.2g.0.15mol) were charged into a 2L three-necked flask, and after starting stirring, aluminum trichloride (20.0 g, 0.15mol) was added, and after stirring at room temperature for 1 hour, stirring was carried out at 140 ℃ for 4 hours. After the reaction was complete, the solvent was distilled off under vacuum to give a black solid. Then carrying out ultrasonic treatment in dichloromethane (500 mL) and filtering, concentrating the filtrate in vacuum to obtain brown solid, separating the product M1-01 from the product M2-01 by post column chromatography (room temperature is 25-30 ℃,150g of silica gel is 200-300 meshes, eluent is ethyl acetate and heptane, gradient elution is carried out), respectively concentrating the column-passing liquid to obtain yellow-brown solid, then recrystallizing by ethanol to further purify the product to respectively obtain 13.9g of yellow-brown solid M1-01, wherein the yield is 40.4%; 12.2g of M2-01 as a yellowish brown solid are obtained in a yield of 35.6%.
(2) M1-01 (34.3 g, 0.1mol) and 600mL of dichloromethane are added into a 2L three-necked bottle, stirring is started, aqueous hydrogen peroxide solution (40mL, 0.4mol, 30%) is slowly dropped into the bottle, reaction is carried out at room temperature for 2 hours, 100mL of saturated aqueous sodium bicarbonate solution is added after the reaction is finished, stirring and liquid separation are carried out, white solid is obtained by spin-drying, dichloromethane column chromatography is carried out, solvent is spin-dried through column chromatography, 33.2g of white solid is obtained, intermediate M1 is obtained, and the yield is 88.5%.
Product MS (m/e): 373.9; elemental analysis (C) 16 H 7 BrO 4 S): theoretical value C:51.22%, H:1.88 percent; measured value C:51.12%, H:1.78 percent.
(3) Replacing M1-01 with M2-01, and obtaining an intermediate M2 in the same way as the step (2).
Product MS (m/e): 373.9; elemental analysis (C) 16 H 7 BrO 4 S): theoretical value C:51.22%, H:1.88 percent; found value C:51.18%, H:1.93 percent.
Synthesis of intermediates M3 and M4
Figure BDA0002938659720000091
Reference intermediates M1 and M2, synthesis method using
Figure BDA0002938659720000092
Instead of the former
Figure BDA0002938659720000093
Selecting a proper material ratio, and obtaining the intermediates M3 and M4 by using other raw materials and steps which are the same as the synthesis method of the intermediates M1 and M2.
M3: product MS (m/e): 373.9; elemental analysis (C) 16 H 7 BrO 4 S): theoretical value C:51.22%, H:1.88 percent; measured value C:51.24%, H:1.69 percent.
M4: product MS (m/e): 373.9; elemental analysis (C) 16 H 7 BrO 4 S): theoretical value C:51.22%, H:1.88 percent; measured value C:51.31%, H:1.74 percent.
Synthesis of intermediate M5
Figure BDA0002938659720000101
Synthesis of reference intermediate M1, using
Figure BDA0002938659720000102
Respectively replace
Figure BDA0002938659720000103
Selecting a proper material ratio, and obtaining an intermediate M5 by using other raw materials and steps which are the same as the synthesis method of the intermediate M1.
Product MS (m/e): 373.9; elemental analysis (C) 16 H 7 BrO 4 S): theoretical value C:51.22%, H:1.88 percent; found value C:51.32%, H:1.68 percent.
Synthesis of intermediate M6
Figure BDA0002938659720000104
Synthesis of reference intermediate M1, using
Figure BDA0002938659720000105
Respectively replace
Figure BDA0002938659720000106
Figure BDA0002938659720000107
Selecting a proper material ratio, and obtaining an intermediate M6 by using other raw materials and steps which are the same as the synthesis method of the intermediate M1.
Product MS (m/e): 373.9; elemental analysis (C) 16 H 7 BrO 4 S): theoretical value C:51.22%, H:1.88 percent; found value C:51.36%, H:1.67 percent.
Synthesis of intermediate M7
Figure BDA0002938659720000108
Synthesis of reference intermediate M1, using
Figure BDA0002938659720000109
Respectively replace
Figure BDA00029386597200001010
Selecting a proper material ratio, and obtaining an intermediate M7 by using other raw materials and steps which are the same as the synthesis method of the intermediate M1.
Product MS (m/e): 373.9; elemental analysis (C) 16 H 7 BrO 4 S): theoretical value C:51.22%, H:1.88 percent; found value C:51.29%, H:1.67 percent.
Synthesis of intermediates M8 and M9
Figure BDA0002938659720000111
Reference intermediates M1 and M2, synthesis method using
Figure BDA0002938659720000112
Substitution
Figure BDA0002938659720000113
Selecting proper material ratio, and obtaining the intermediates M8 and M9 by the same synthesis method of the intermediates M1 and M2 and other raw materials and steps.
M8: product MS (m/e): 454.1 of the raw materials; elemental analysis (C) 16 H 6 Br 2 O 4 S): theoretical value C:42.32%, H:1.33 percent; found value C:42.37%, H:1.40 percent.
M9: product MS (m/e): 454.1 of the raw materials; elemental analysis (C) 16 H 6 Br 2 O 4 S): theoretical value C:42.32%, H:1.33 percent; found value C:42.46%, H:1.39 percent.
Synthesis of intermediates M10 and M11
Figure BDA0002938659720000114
Reference intermediates M1 and M2, synthesis method using
Figure BDA0002938659720000115
Substitution
Figure BDA0002938659720000116
Selecting a proper material ratio, and obtaining the intermediates M10 and M11 by using other raw materials and steps which are the same as the synthesis method of the intermediates M1 and M2.
M10: product MS (m/e): 409.9; elemental analysis (C) 16 H 6 BrClO 4 S): theoretical value C:46.91%, H:1.48 percent; measured value C:46.87%, H:1.42 percent.
M11: product MS (m/e): 409.9; elemental analysis (C) 16 H 6 BrClO 4 S): theoretical value C:46.91%, H:1.48 percent; found value C:46.92%, H:1.51 percent.
Synthesis of intermediates M12 and M13
Figure BDA0002938659720000121
Reference intermediates M1 and M2, synthesis method using
Figure BDA0002938659720000122
Instead of the former
Figure BDA0002938659720000123
Selecting a proper material ratio, and obtaining the intermediates M12 and M13 by using other raw materials and steps which are the same as the synthesis method of the intermediates M1 and M2.
M12: product MS (m/e): 409.9; elemental analysis (C) 16 H 6 BrClO 4 S): theoretical value C:46.91%, H:1.48 percent; measured value C:46.84%, H:1.53 percent.
M13: product MS (m/e): 409.9; elemental analysis (C) 16 H 6 BrClO 4 S): theoretical value C:46.91%, H:1.48 percent; found value C:46.73%, H:1.61 percent.
Synthesis of intermediate M14
Figure BDA0002938659720000124
Synthesis of reference intermediate M1, using
Figure BDA0002938659720000125
Respectively substitute
Figure BDA0002938659720000126
Figure BDA0002938659720000127
And selecting a proper material ratio, and obtaining an intermediate M14 by the same synthesis method of the intermediate M1 and other raw materials and steps.
Product MS (m/e): 409.9; elemental analysis (C) 16 H 6 BrClO 4 S): theoretical value C:46.91%, H:1.48 percent; found value C:46.85%, H:1.47 percent.
Synthesis of intermediate M15
Figure BDA0002938659720000131
Synthesis of reference intermediate M1, using
Figure BDA0002938659720000132
Respectively substitute
Figure BDA0002938659720000133
Figure BDA0002938659720000134
And selecting a proper material ratio, and obtaining an intermediate M15 by the same synthesis method of the intermediate M1 and other raw materials and steps.
Product MS (m/e): 453.8; elemental analysis (C) 16 H 6 Br 2 O 4 S): theoretical value C:42.32%, H:1.33 percent; found value C:42.36%, H:1.41 percent.
EXAMPLE 1 Synthesis of Compound I-1
Figure BDA0002938659720000135
The synthetic route is as follows:
Figure BDA0002938659720000136
into a 1L three-necked flask, M3 (37.7g, 0.1mol), phenylboronic acid (18.3g, 0.1mol), sodium carbonate (15.9g, 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). Heating and refluxing for reaction (the temperature in the system is 70-80 ℃) for 3 hours, and stopping the reaction. The solvent was evaporated off, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered, column-chromatographed with petroleum ether/ethyl acetate (2.
Product MS (m/e): 374.41; elemental analysis (C) 22 H 14 O 4 S): theoretical value C:70.58%, H:3.77 percent; found value C:70.51%, H:3.79 percent.
EXAMPLE 2 Synthesis of Compound I-2
Figure BDA0002938659720000141
The synthetic route is as follows:
Figure BDA0002938659720000142
m1 is used for replacing M3, and p-methyl phenylboronic acid is used for replacing phenylboronic acid, the proper material ratio is selected, other raw materials and steps are the same as those in example 1, and 32.9g of light yellow solid I-2 is obtained, and the yield is 84.7%.
Product MS (m/e): 388.08 of the total weight of the mixture; elemental analysis (C) 23 H 16 O 4 S): theoretical value C:71.12%, H:4.15 percent; found value C:71.15%, H:4.18 percent.
EXAMPLE 3 Synthesis of Compound I-5
Figure BDA0002938659720000143
The synthetic route is as follows:
Figure BDA0002938659720000144
m6 is used for replacing M3, and p-cyclohexylphenylboronic acid is used for replacing phenylboronic acid, a proper material ratio is selected, other raw materials and steps are the same as those in example 1, and 40g of light yellow solid I-5 is obtained, and the yield is 85.1%.
Product MS (m/e): 456.14; elemental analysis (C) 28 H 24 O 4 S): theoretical value C:73.66%, H:5.3 percent; found value C:73.70%, H:5.26 percent.
EXAMPLE 4 Synthesis of Compound I-6
Figure BDA0002938659720000151
The synthetic route is as follows:
Figure BDA0002938659720000152
using M4 instead of M3, 3-biphenylboronic acid instead of phenylboronic acid, selecting a suitable ratio of materials, the other materials and procedures were the same as in example 1, yielding 36.5g of pale yellow solid I-6 with a yield of 81.2%.
Product MS (m/e): 450.51 of the total weight of the mixture; elemental analysis (C) 28 H 18 O 4 S): theoretical value C:74.65%, H:4.03 percent; found value C:74.67%, H:4.01 percent.
EXAMPLE 5 Synthesis of Compound I-8
Figure BDA0002938659720000153
The synthetic route is as follows:
Figure BDA0002938659720000154
the M7 is used for replacing the M3, 2-naphthalene boric acid for replacing the phenylboronic acid, the proper material ratio is selected, other raw materials and steps are the same as those of the example 1, and 35.3 light yellow solid I-8 is obtained, and the yield is 83.3%.
Product MS (m/e): 450.09; elemental analysis (C) 28 H 18 O 4 S): theoretical value C:73.57%, H:3.80 percent; found value C:73.60%, H:3.78 percent.
EXAMPLE 6 Synthesis of Compound I-13
Figure BDA0002938659720000161
The synthetic route is as follows:
Figure BDA0002938659720000162
the M2 was used instead of the M3, 9-phenanthreneboronic acid instead of the phenylboronic acid, the appropriate material ratio was chosen, the other raw materials and the procedure were the same as in example 1, and 42.0g of pale yellow solid I-13 was obtained with a yield of 75.5%.
Product MS (m/e): 550.12 of the total weight of the mixture; elemental analysis (C) 36 H 22 O 4 S): theoretical value C:78.53%, H:4.03 percent; measured value C:78.55%, H:4.01 percent.
EXAMPLE 7 Synthesis of Compound I-16
Figure BDA0002938659720000163
The synthetic route is as follows:
Figure BDA0002938659720000164
using M5 instead of M3 and triphenylene-2-boronic acid instead of phenylboronic acid, the appropriate material ratios were chosen and the other starting materials and procedures were the same as in example 1, giving 41g of I-16 as a pale yellow solid in 78.3% yield.
Product MS (m/e): 524.11; elemental analysis (C) 34 H 20 O 4 S): theoretical value C:77.85%, H:3.84 percent; measured value C:77.89%, H:3.83 percent.
EXAMPLE 8 Synthesis of Compound I-27
Figure BDA0002938659720000171
The synthetic route is as follows:
Figure BDA0002938659720000172
substituting M8 for M3, 5-dimethylphenylboronic acid for phenylboronic acid, selecting appropriate ratios of materials, the other materials and procedures were the same as in example 1 to give 39.2 pale yellow solid I-27 with a yield of 77.4%.
Product MS (m/e): 506.16; elemental analysis (C) 28 H 18 O 4 S): theoretical value C:75.87%, H:5.17 percent; measured value C:75.90%, H:5.15 percent.
EXAMPLE 9 Synthesis of Compound I-28
Figure BDA0002938659720000173
The synthetic route is as follows:
Figure BDA0002938659720000174
using M9 instead of M3, 4-isopropylphenylboronic acid instead of phenylboronic acid, the appropriate material ratios were chosen and the other raw materials and procedures were the same as in example 1 to give 31.8g of pale yellow solid I-28 in 71.3% yield.
Product MS (m/e): 534.19 of the total weight of the mixture; elemental analysis (C) 34 H 30 O 4 S): theoretical value C:76.38%, H:5.66 percent; measured value C:76.41 percent，H：5.69％。
EXAMPLE 10 Synthesis of Compounds I-32
Figure BDA0002938659720000181
The synthetic route is as follows:
Figure BDA0002938659720000182
into a 1L three-necked flask, M10 (41.2 g, 0.1mol), 3, 4-dimethylbenzeneboronic acid (15g, 0.1mol), sodium carbonate (15.9g, 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). Heating and refluxing for reaction (the temperature in the system is 70-80 ℃) for 3 hours, and stopping the reaction. The solvent was evaporated, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered, column-chromatographed with petroleum ether/ethyl acetate (2.
Product MS (m/e): 436.05; elemental analysis (C) 24 H 17 ClO 4 S): theoretical value C:65.98%, H:3.92 percent; found value C:65.72%, H:3.89 percent.
A1L three-necked flask was charged with I-32-1 (43.7 g, 0.1mol), 1-naphthalene boronic acid (17.2g, 0.1mol), cesium carbonate (39g, 0.12mol) and dioxane (400 ml) in this order under magnetic stirring and nitrogen exchange, and then stirred. 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 37.3g of pale yellow solid I-32 with the yield of 69.8%.
Product MS (m/e): 528.62; elemental analysis (C) 34 H 24 O 4 S): theoretical value C:77.25%, H:4.58 percent; found value C:77.29%, H:4.55 percent.
EXAMPLE 11 Synthesis of Compound I-33
Figure BDA0002938659720000183
The synthetic route is as follows:
Figure BDA0002938659720000191
using M11 instead of M10, 4-isopropylphenylboronic acid instead of 3, 4-dimethylphenylboronic acid, selecting an appropriate material ratio, and using the same raw materials and procedures as in example 10, 34.5g of pale yellow solid I-33-1 was obtained first, with a yield of 72.0%, and using I-33-1 instead of I-32-1, 4-phenyl-1-naphthylboronic acid instead of 1-naphthylboronic acid, 52.4g of pale yellow solid I-33 was obtained, with a yield of 84.7%.
I-33-1: product MS (m/e): 496.0; elemental analysis (C) 28 H 13 ClO 5 S): theoretical value C:67.68%, H:2.64 percent; found value C:67.71%, H:2.55 percent.
I-33: product MS (m/e): 618.2; elemental analysis (C) 41 H 30 O 4 S): theoretical value C:79.59%, H:4.89%; found value C:79.63%, H:4.86 percent.
EXAMPLE 12 Synthesis of Compound I-50
Figure BDA0002938659720000192
The synthetic route is as follows:
Figure BDA0002938659720000193
m12 is used for replacing M10, 2-naphthalene boric acid for replacing 3, 4-dimethyl benzene boric acid, a proper material ratio is selected, other raw materials and steps are the same as those of the example 10, 33.9g of light yellow solid I-50-1 is obtained firstly, the yield is 73.8%, I-32-1 is replaced by I-50-1, and benzene boric acid is used for replacing 1-naphthalene boric acid, 43.3g of light yellow solid I-50 is obtained, and the yield is 86.5%.
I-50-1: product MS (m/e): 458.04; elemental analysis (C) 26 H 15 ClO 4 S): theoretical value C:68.05%, H:3.29 percent; measured value C:68.08%, H:3.25 percent.
I-50: product MS (m/e): 500.11 of the total weight of the mixture; elemental analysis (C) 32 H 20 O 4 S): theoretical value C:76.78%, H:4.03 percent; found value C:76.71%, H:4.00 percent.
EXAMPLE 13 Synthesis of Compound I-51
Figure BDA0002938659720000201
The synthetic route is as follows:
Figure BDA0002938659720000202
m14 is used for replacing M12, 2-naphthalene boric acid for replacing 3, 4-dimethyl benzene boric acid, a proper material ratio is selected, other raw materials and steps are the same as those of the example 12, 36.2g of light yellow solid I-51-1 is obtained firstly, the yield is 78.2%, and I-51-1 is used for replacing I-32-1, 43.1g of light yellow solid I-51 is obtained, and the yield is 83.6%.
I-51-1: product MS (m/e): 458.04; elemental analysis (C) 26 H 15 ClO 4 S): theoretical value C:68.05%, H:4.03 percent; found value C:68.07%, H:4.01 percent.
I-51: product MS (m/e): 514.12 of the basic material; elemental analysis (C) 33 H 22 O 4 S): theoretical value C:77.02%, H:4.31 percent; measured value C:77.06%, H:4.27 percent.
EXAMPLE 14 Synthesis of Compound I-52
Figure BDA0002938659720000203
The synthetic route is as follows:
Figure BDA0002938659720000204
m13 is used for replacing M12, 4-biphenylboronic acid for replacing 3, 4-dimethylbenzeneboronic acid, a proper material ratio is selected, other raw materials and steps are the same as those of the example 12, 38.3g of light yellow solid I-52-1 is obtained firstly, the yield is 79%, I-32-1 is replaced by I-52-1, and 44.7 light yellow solid I-52 is obtained, and the yield is 84.9%.
I-52-1: product MS (m/e): 484.05; elemental analysis (C) 28 H 17 ClO 4 S): theoretical value C:69.35%, H:3.53 percent; found value C:69.38%, H:3.50 percent.
I-52: product MS (m/e): 526.12 of the total weight of the steel; elemental analysis (C) 34 H 22 O 4 S): theoretical value C:77.55%, H:4.21 percent; measured value C:77.57%, H:4.24 percent.
EXAMPLE 15 Synthesis of Compound I-53
Figure BDA0002938659720000211
The synthetic route is as follows:
Figure BDA0002938659720000212
the appropriate material ratio was chosen by substituting M15 for M3, and the other starting materials and procedures were the same as in example 1, to give 38.8g of I-53 as a pale yellow solid in 86.1% yield.
Product MS (m/e): 450.09; elemental analysis (C) 28 H 18 O 4 S): theoretical value C:74.65%, H:4.03 percent; found value C:74.68%, H:4.00 percent.
According to the synthesis methods of examples 1 to 15, other compounds in I-1 to I-56 can be synthesized by simply replacing the corresponding raw materials without changing any substantial operation.
Example 16
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)/one of the compounds (40 nm)/LiF (1 nm)/Al provided in examples 1 to 15, the preparation process was:
(1) Carrying out ultrasonic treatment on a glass substrate coated with an ITO transparent conducting layer in a commercial cleaning agent, washing in deionized water, carrying out ultrasonic oil removal in an acetone-ethanol mixed solvent (volume ratio is 1: 1), baking in a clean environment until water is completely removed, cleaning 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 (nitrogen-phosphorus) 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 BDA0002938659720000221
(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 AND AND BD01 are as follows:
Figure BDA0002938659720000222
(4) Taking any one of the compounds provided in the embodiments 1 to 15 as an electron transport material of an electron transport layer of the device, and continuously performing vacuum evaporation on the EML luminescent layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 40nm to obtain the electron transport layer;
(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; a series of OLED devices provided by the invention are obtained.
Following the same procedure as above, only the electron transport material in step (4) was replaced with the following commercial BPhen comparative compound, the structural formula of which is shown below, to obtain comparative device OLED-11.
Figure BDA0002938659720000223
Comparative compounds.
The invention detects the performance of the devices OLED-1 to OLED-11. The results are shown in Table 1.
TABLE 1
Figure BDA0002938659720000231
From the above results, it can be seen that the current efficiencies of the devices OLED-1 to OLED-10 prepared by using the compound provided by the present invention are relatively high, and the operating voltage is significantly lower than that of the device OLED-11 using the comparative compound Bphen as the electron transport material under the same brightness condition.
The results show that the novel organic material is used for the organic electroluminescent device, can effectively reduce the driving voltage and improve the current efficiency, and is an electron transport material with good performance.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.

Claims (8)

1. A naphthoquinone heterocyclic compound having a structure represented by general formula (i):
Figure FDA0003849378610000011
wherein:
R 1 ～R 8 at least one of which is substituted or unsubstituted C 6 ～C 40 A monocyclic or polycyclic aromatic hydrocarbon group of (A), said R 1 ～R 8 In addition to represents substituted or unsubstituted C 6 ～C 40 The rest of the monocyclic aromatic hydrocarbon group or polycyclic aromatic hydrocarbon group is H atom;
said substituted or unsubstituted C 6 ～C 40 The monocyclic aromatic hydrocarbon group or polycyclic aromatic hydrocarbon group of (a) is optionally selected from the following groups:
Figure FDA0003849378610000012
Figure FDA0003849378610000021
2. a compound of claim 1, wherein R is 1 ～R 8 Wherein any one group is said substituted or unsubstituted C 6 ～C 40 The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a);
or, said R 1 ～R 8 Wherein two are said substituted or unsubstituted C 6 ～C 40 The monocyclic aromatic hydrocarbon group or the polycyclic aromatic hydrocarbon group of (a), the two groups being located on different benzene rings, or on the same benzene ring; the two groups may be the same or different from each other.
3. The compound of claim 1, wherein the compound is selected from the group consisting of compounds represented by the following structural formulae:
Figure FDA0003849378610000031
Figure FDA0003849378610000041
4. use of a naphthoquinone heterocyclic compound as defined in any one of claims 1 to 3 for the preparation of an organic electroluminescent device.
5. The use according to claim 4, wherein the naphthoquinone heterocycle compound is used as an electron transport material in an organic electroluminescent device.
6. An organic electroluminescent device comprising an electron transport layer, wherein the material of the electron transport layer contains the naphthoquinone-based heterocyclic compound according to any one of claims 1 to 3.
7. A display device comprising the organic electroluminescent element according to claim 6.
8. An illumination apparatus comprising the organic electroluminescent device according to claim 6.
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