CN109593042A - A kind of electroluminescent organic material and the organic electroluminescence device comprising it - Google Patents

A kind of electroluminescent organic material and the organic electroluminescence device comprising it Download PDF

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CN109593042A
CN109593042A CN201811581701.3A CN201811581701A CN109593042A CN 109593042 A CN109593042 A CN 109593042A CN 201811581701 A CN201811581701 A CN 201811581701A CN 109593042 A CN109593042 A CN 109593042A
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substituted
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unsubstituted carbon
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CN109593042B (en
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马天天
杨雷
李红燕
冯震
孙占义
王亚龙
李健
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Shaanxi Smythe Wright Photoelectric Material Co Ltd
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Abstract

The present invention provides a kind of electroluminescent organic material and the organic electroluminescence device comprising it, belongs to electroluminescent technology field.The present invention introduces adamantane as new core group, changes molecular conformation, reduce the symmetry of structure on the basis of bis- (triarylamine) symmetrical structures, to promote material filming；Adamantane group itself has biggish steric hindrance and rigid structure, while its unconjugated molecular structure will not influence the electron energy level of triarylamine, ensure that the hole transport performance of material；The compound of the group of the present invention containing adamantane has excellent hole transport performance, it can be used for making organic electroluminescence device, especially as the hole transport layer material in organic electroluminescence device, the luminous efficiency and service life of organic luminescent device can be effectively improved.

Description

A kind of electroluminescent organic material and the organic electroluminescence device comprising it
Technical field
The present invention relates to a kind of electroluminescent organic material and its as organic electroluminescence device hole-transporting layer material The application of material, and in particular to electroluminescent organic material and the organic electroluminescence device comprising it belong to electroluminescent field.
Background technique
Electroluminescent (Electroluminescence), and electroluminescence can be claimed, abbreviation EL is by being added in two electrodes Voltage generate electric field, by electric field excite electronics hit the centre of luminescence, and be led to electronics transition between energy level, variation, answer Conjunction leads to a kind of luminous physical phenomenon.In recent years, organic electroluminescence device (OLED:Organic Electroluminescent device) visual field of people is progressed into as display technology of new generation.OLED is one kind by more The electroluminescent device that layer organic thin film structure is formed, organic film therein are using vapor deposition, vapor deposition or spin coating proceeding in base The film of the luminous organic material formed on plate.Compared with traditional display technology, in voltage characteristic, light emission luminance, shine effect Rate, chromaticness, response speed and appreciative perspective etc. very advantageous, and it is at low cost, therefore possess vast market prospect.
In order to improve brightness, efficiency and the service life of organic electroluminescence device, multilayered structure is usually used in the devices.This A little multilayered structures include: hole injection layer (hole injection layer), hole transmission layer (hole transport Layer), electronic barrier layer ((electron-blocking layer), luminescent layer (emitting layer) and electron-transport Layer (electron transport layer) etc..These organic layers, which have, improves carrier (hole and electronics) in each stratum boundary Injection efficiency between face, the ability that equilbrium carrier transmits between the layers, to improve the brightness and efficiency of device.
Although the technology is still currently, the electroluminescent organic material of a large amount of function admirables developed successively There are many problems, how to design the better material of new performance and are adjusted, so that all devices can reach reduction electricity It presses, improve efficiency effect with the service life, be always those skilled in the art's urgent problem to be solved.
Summary of the invention
The purpose of the present invention is to provide a kind of with high-fire resistance and excellent chemical stability and can be used as sky The electroluminescent organic material of cave implanted layer, hole transporting layer or electronic blocking layer material etc..
Another object of the present invention is to provide a kind of organic luminescent device comprising the electroluminescent organic material, tools There are lower driving voltage, higher luminous efficiency and service life.
To achieve the above object, the present invention adopts the following technical scheme that:
A kind of electroluminescent organic material, the structural formula of the material as described in chemical formula 1:
Ar1、Ar2、Ar5With Ar6It is identical or different, it is separately 1-20 selected from substituted or unsubstituted carbon atom number Alkyl, substituted or unsubstituted carbon atom number be 2-20 alkenyl, substituted or unsubstituted carbon atom number be 2-24 alkynyl, Heterocyclylalkyl that naphthenic base that substituted or unsubstituted carbon atom number is 3-20, substituted or unsubstituted carbon atom number are 2-20, Heteroarylalkyl that aralkyl that substituted or unsubstituted carbon atom number is 7-30, substituted or unsubstituted carbon atom number are 2-30, Aryl that substituted or unsubstituted carbon atom number is 6-30, substituted or unsubstituted carbon atom number are one in the heteroaryl of 1-30 Kind；
Ar3And Ar4It is identical or different, separately selected from singly-bound, the Asia that substituted or unsubstituted carbon atom number is 1-20 The sub- alkynes that alkenylene that alkyl, substituted or unsubstituted carbon atom number are 2-20, substituted or unsubstituted carbon atom number are 2-24 The heterocycle that ring alkylidene that base, substituted or unsubstituted carbon atom number are 3-20, substituted or unsubstituted carbon atom number are 2-20 Sub- aralkyl that alkylidene, substituted or unsubstituted carbon atom number are 7-30, substituted or unsubstituted carbon atom number are 2-30's Arlydene that miscellaneous Asia aralkyl, substituted or unsubstituted carbon atom number are 6-30, substituted or unsubstituted carbon atom number are 1-30 Heteroarylidene, the ring alkenylene of substituted or unsubstituted carbon atom number 3-15, substituted or unsubstituted carbon atom number 2-15 One of miscellaneous alkenylene, miscellaneous alkynylene of substituted or unsubstituted carbon atom number 2-15；
The Ar1、Ar2、Ar3、Ar4、Ar5With Ar6Substituent group it is identical or different, and separately be selected from deuterium, cyanogen Base, nitro, halogen, hydroxyl, the alkyl of substituted or unsubstituted carbon atom number 1-20, substituted or unsubstituted carbon atom number 3-20 Naphthenic base, the alkenyl of substituted or unsubstituted carbon atom number 2-20, substituted or unsubstituted carbon atom number 2-24 alkynyl, take Generation or the Heterocyclylalkyl of unsubstituted carbon atom number 2-20, substituted or unsubstituted carbon atom number 7-20 aralkyl, replace or The aryl, substituted or unsubstituted of the heteroarylalkyl of unsubstituted carbon atom number 2-20, substituted or unsubstituted carbon atom number 6-20 The heteroaryl of carbon atom number 1-20, the alkoxy of substituted or unsubstituted carbon atom number 1-20, substituted or unsubstituted carbon it is former Subnumber is the alkylthio group of 1-20, the alkylamino of substituted or unsubstituted carbon atom number 1-20, substituted or unsubstituted carbon atom number The fragrant amino of 6-20, the heteroaryl amino of substituted or unsubstituted carbon atom number 1-20, substituted or unsubstituted carbon atom number 7-20 Arylalkylamino, substituted or unsubstituted carbon atom number be the aIkylsilyl groups of 1-20, substituted or unsubstituted carbon atom number For the arylsilyl groups of 6-24, substituted or unsubstituted carbon atom number be 6-20 aryloxy group, substituted or unsubstituted carbon it is former Subnumber is one of 6-20 arylthio.
A further improvement of the present invention lies in that the Ar1、Ar2、Ar5With Ar6It is identical or different, separately it is selected from Heteroarylalkyl that aralkyl that substituted or unsubstituted carbon atom number is 7-30, substituted or unsubstituted carbon atom number are 2-30, Aryl that substituted or unsubstituted carbon atom number is 6-30, substituted or unsubstituted carbon atom number are one in the heteroaryl of 1-30 Kind.
A further improvement of the present invention lies in that the Ar3、Ar4The Asia for being 6-30 selected from substituted or unsubstituted carbon atom number The Asia that heteroarylidene that aryl, substituted or unsubstituted carbon atom number are 1-30, substituted or unsubstituted carbon atom number are 7-30 Aralkyl, substituted or unsubstituted carbon atom number are one of miscellaneous sub- aralkyl of 2-30.
A further improvement of the present invention lies in that the chemical formula 1 is such as one of flowering structure:
A further improvement of the present invention lies in that the Ar3、Ar4Selected from substituted or unsubstituted phenyl, substituted or unsubstituted Xenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted dimethyl fluorenyl, One of substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene.
A kind of organic electroluminescence device, including cathode, anode and one layer or more between the cathode and anode Organic layer, at least one layer of in one layer or more organic layer between the cathode and anode includes electroluminescent hair described in claim 1 Luminescent material.
A further improvement of the present invention lies in that the organic layer is selected from hole injection layer, hole transmission layer, electronic blocking Layer, luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer.
A further improvement of the present invention lies in that the organic matter layer comprising electroluminescent material described in claim 1 is sky Cave transport layer.
Compared with prior art, the invention has the benefit that
1. the present invention introduces adamantane as new core base on the basis of bis- (triarylamine) symmetrical structures Group, changes molecular conformation, reduces the symmetry of structure, to promote material filming；
2. adamantane group itself has biggish steric hindrance and rigid structure, while its unconjugated molecular structure is not The electron energy level that will affect triarylamine ensure that the hole transport performance of material；
3. the adamantane group in molecular center position can also be by the protective effect of two sides triarylamine, can be one Determine degree inhibition its isomerization/dehydrogenation reaction occurs at high temperature, to improve the purity and device performance of material；
4. the compound of the group of the present invention containing adamantane has excellent hole transport performance, can be used for making organic Electroluminescent device can effectively improve organic hair especially as the hole transport layer material in organic electroluminescence device The luminous efficiency and service life of optical device.
Detailed description of the invention
Fig. 1 is the structural schematic diagram of electroluminescent organic material of the invention.
Specific embodiment
Hereinafter, by embodiment, the present invention is described in more detail.But following embodiments are only examples of the invention Show, and and the non-limiting present invention.
Referring to Fig. 1, a kind of electroluminescent organic material of the invention, the structural formula of the material as described in chemical formula 1:
Ar1、Ar2、Ar5With Ar6It is identical or different, it is separately 1-20 selected from substituted or unsubstituted carbon atom number Alkyl, substituted or unsubstituted carbon atom number be 2-20 alkenyl, substituted or unsubstituted carbon atom number be 2-24 alkynyl, Heterocyclylalkyl that naphthenic base that substituted or unsubstituted carbon atom number is 3-20, substituted or unsubstituted carbon atom number are 2-20, Heteroarylalkyl that aralkyl that substituted or unsubstituted carbon atom number is 7-30, substituted or unsubstituted carbon atom number are 2-30, Aryl that substituted or unsubstituted carbon atom number is 6-30, substituted or unsubstituted carbon atom number are one in the heteroaryl of 1-30 Kind；
Ar3And Ar4It is identical or different, separately selected from singly-bound, the Asia that substituted or unsubstituted carbon atom number is 1-20 The sub- alkynes that alkenylene that alkyl, substituted or unsubstituted carbon atom number are 2-20, substituted or unsubstituted carbon atom number are 2-24 The heterocycle that ring alkylidene that base, substituted or unsubstituted carbon atom number are 3-20, substituted or unsubstituted carbon atom number are 2-20 Sub- aralkyl that alkylidene, substituted or unsubstituted carbon atom number are 7-30, substituted or unsubstituted carbon atom number are 2-30's Arlydene that miscellaneous Asia aralkyl, substituted or unsubstituted carbon atom number are 6-30, substituted or unsubstituted carbon atom number are 1-30 Heteroarylidene, the ring alkenylene of substituted or unsubstituted carbon atom number 3-15, substituted or unsubstituted carbon atom number 2-15 One of miscellaneous alkenylene, miscellaneous alkynylene of substituted or unsubstituted carbon atom number 2-15；
The Ar1、Ar2、Ar3、Ar4、Ar5With Ar6Substituent group it is identical or different, and separately be selected from deuterium, cyanogen Base, nitro, halogen, hydroxyl, the alkyl of substituted or unsubstituted carbon atom number 1-20, substituted or unsubstituted carbon atom number 3-20 Naphthenic base, the alkenyl of substituted or unsubstituted carbon atom number 2-20, substituted or unsubstituted carbon atom number 2-24 alkynyl, take Generation or the Heterocyclylalkyl of unsubstituted carbon atom number 2-20, substituted or unsubstituted carbon atom number 7-20 aralkyl, replace or The aryl, substituted or unsubstituted of the heteroarylalkyl of unsubstituted carbon atom number 2-20, substituted or unsubstituted carbon atom number 6-20 The heteroaryl of carbon atom number 1-20, the alkoxy of substituted or unsubstituted carbon atom number 1-20, substituted or unsubstituted carbon it is former Subnumber is the alkylthio group of 1-20, the alkylamino of substituted or unsubstituted carbon atom number 1-20, substituted or unsubstituted carbon atom number The fragrant amino of 6-20, the heteroaryl amino of substituted or unsubstituted carbon atom number 1-20, substituted or unsubstituted carbon atom number 7-20 Arylalkylamino, substituted or unsubstituted carbon atom number be the aIkylsilyl groups of 1-20, substituted or unsubstituted carbon atom number For the arylsilyl groups of 6-24, substituted or unsubstituted carbon atom number be 6-20 aryloxy group, substituted or unsubstituted carbon it is former Subnumber is one of 6-20 arylthio.
Specifically, the Ar1、Ar2、Ar5With Ar6It is identical or different, separately it is selected from substituted or unsubstituted carbon Heteroarylalkyl that aralkyl that atomicity is 7-30, substituted or unsubstituted carbon atom number are 2-30, substituted or unsubstituted carbon Aryl that atomicity is 6-30, substituted or unsubstituted carbon atom number are one of heteroaryl of 1-30.
Specifically, the Ar3、Ar4Selected from the arlydene that substituted or unsubstituted carbon atom number is 6-30, replaces or do not take Sub- aralkyl that heteroarylidene that the carbon atom number in generation is 1-30, substituted or unsubstituted carbon atom number are 7-30, substitution or not Substituted carbon atom number is one of miscellaneous sub- aralkyl of 2-30.
Specifically, the chemical formula 1 is such as one of flowering structure:
Heretofore described Ar3、Ar4Selected from substituted or unsubstituted phenyl, substituted or unsubstituted xenyl, substitution or Unsubstituted terphenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted dimethyl fluorenyl, substituted or unsubstituted two One of benzofuranyl, substituted or unsubstituted dibenzothiophene.
A kind of organic electroluminescence device based on above-mentioned electroluminescent organic material, including cathode, anode and in institute One layer or more organic layer possessed by stating between cathode and anode, it is at least one layer of comprising upper in described one layer or more of organic layer The electroluminescent material stated.
The organic layer includes hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electronics Transport layer and electron injecting layer.
Organic matter layer comprising the electroluminescent organic material is hole transmission layer.
" alkyl " unsubstituted in the present invention refers to that carbon atom number is the alkyl of 1-20, is 1-20 comprising carbon atom number Straight chained alkyl or carbon atom number be 1-6 branched alkyl.For example, methyl, ethyl, propyl, isobutyl group, sec-butyl, amyl, Isopentyl, base etc..Substituted carbon atom number be 1-20 alkyl refer at least one hydrogen atom by D-atom, F, Cl, I, CN, Hydroxyl, nitro, amino etc. replace.
Unsubstituted alkenyl in the present invention, the carbon atom number referred to are the alkenyl of 2-20, the carbon comprising carbon-carbon double bond Atomicity is the alkenyl of the straight chain of 2-20, or the alkenyl comprising the branch that carbon atom number is 1-6.Such as: vinyl, acrylic, Allyl, isopropenyl, 2- cyclobutenyl etc..The alkenyl that substituted carbon atom number is 2-20 refers at least one hydrogen atom by deuterium original Son, F, Cl, I, CN, hydroxyl, nitro, amino etc. replace.Unsubstituted alkynyl in the present invention, the carbon atom number referred to are 2- 24 alkynyl, the carbon atom number comprising triple carbon-carbon bonds are the straight-chain alkynyl of 2-24, or the alkynes comprising the branch that carbon atom number is 1-7 Base.Such as: acetenyl, 2-propynyl etc..The alkynyl that substituted carbon atom number is 2-24 refers at least one hydrogen atom by deuterium original Son, F, Cl, I, CN, hydroxyl, nitro, amino etc. replace.
Unsubstituted aryl in the present invention, the carbon atom number referred to are the aryl of 6-30.Such as: phenyl, naphthalene, pyrene Base, dimethyl fluorenyl, anthryl, phenanthryl,Base, camomile ring group, acenaphthenyl, xenyl, benzo anthryl, two fluorenyl of spiral shell, base, indenyl Deng.Substituted carbon atom number be 6-30 aryl refer at least one hydrogen atom by D-atom, F, Cl, I, CN, hydroxyl, nitro, Amino etc. replaces.
Unsubstituted aralkyl in the present invention refers to that carbon atom number is the aralkyl of 7-30.Such as: tolyl, diformazan Base fluorenyl etc..Substituted carbon atom number be 7-30 aralkyl refer at least one hydrogen atom by D-atom, F, Cl, I, CN, Hydroxyl, nitro, amino etc. replace.
The unsubstituted heteroaryl of the present invention refers to that carbon atom number is the heteroaryl of 2-30.Such as: pyridyl group, pyrazinyl, Pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, indyl, carbazyl, dibenzofuran group, dibenzothiophene, dibenzo selenium Pheno base etc..Substituted carbon atom number be 2-30 heteroaryl refer at least one hydrogen atom by D-atom, F, Cl, I, CN, hydroxyl, Nitro, amino etc. replace.
The unsubstituted naphthenic base of the present invention refers to that carbon atom number is the naphthenic base of 3-20.Such as: cyclopropyl, cyclobutyl, Cyclopenta, cyclohexyl, norborny, adamantyl etc..Substituted carbon atom number is that the naphthenic base of 3-20 refers at least one Hydrogen atom is replaced by D-atom, F, Cl, I, CN, hydroxyl, nitro, amino etc..
The synthesis of compound 1
1,3- adamantane glycol (5.0g, 29.7mmol) and bromobenzene (10.3g, 65.4mmol) are dissolved in methylene chloride In (70mL), under the conditions of 0 DEG C of nitrogen protection, it is slowly added dropwise trifluoromethanesulfonic acid (11.2g, 74.3mmol), after insulated and stirred 8h It is warmed to room temperature, 2mol/L sodium hydrate aqueous solution is added dropwise into reaction solution, so that pH value=7 of reaction solution.Then liquid separation, it is organic It is mutually dry using magnesium sulfate is added after washing, solvent is removed under reduced pressure；Using normal heptane as mobile phase, using silica gel column chromatography to thick It after product are purified, is recrystallized using methylene chloride/n-heptane system, obtains 6.8g white solid intermediate 1-A, yield It is 51%.
By 2 bromo toluene (10.0g, 58.5mmol), 2- amino -9,9- dimethyl fluorene (13.5g, 64.3mmol), three (two BENZYLIDENE ACETONE) two palladiums (1.1g, 1.2mmol), 2- dicyclohexyl phosphorus -2,4,6- tri isopropyl biphenyl (1.1g, 2.3mmol) with And sodium tert-butoxide (8.4g, 87.7mmol) is added in toluene (150mL), is heated to reflux temperature under nitrogen protection, stirs 2h； It is then cooled to room temperature, using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column, decompression removes reaction solution Remove solvent；Recrystallization purification is carried out to crude product using methylene chloride/ethanol system, obtains 11.3g light yellow solid intermediate 1- B, yield 65%.
By intermediate 1-A (6.8g, 15.2mmol), 1-B (10.0g, 33.5mmol), tris(dibenzylideneacetone) dipalladium (0.6g, 0.6mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.5g, 1.2mmol) and sodium tert-butoxide (4.4g, It 45.7mmol) is added in toluene (50mL), is heated to reflux temperature under nitrogen protection, stir 16h；Then it is cooled to room temperature, Solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in reaction solution；Use dichloro Ethane carries out recrystallization purification to crude product, obtains 5.6g compound as white solid 1, yield 42%.Mass spectrum: m/z=883.5 (M +H+)
The synthesis of compound 2
By bromo- 9, the 9- dimethyl fluorene (15.0g, 54.9mmol) of 2-, 4- aminobphenyl (10.2g, 60.4mmol), three (two BENZYLIDENE ACETONE) two palladiums (1.0g, 1.1mmol), 2- dicyclohexyl phosphorus -2,4,6- tri isopropyl biphenyl (1.0g, 2.2mmol) with And sodium tert-butoxide (7.9g, 82.4mmol) is added in toluene (200mL), is heated to reflux temperature under nitrogen protection, stirs 2h； It is then cooled to room temperature, using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column, decompression removes reaction solution Remove solvent；Recrystallization purification is carried out to crude product using methylene chloride/n-heptane system, obtains 14.4g white solid intermediate 2- B, yield 73%.
By intermediate 1-A (5.0g, 11.2mmol), 2-B (8.9g, 24.7mmol), tris(dibenzylideneacetone) dipalladium (0.4g, 0.4mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.4g, 0.9mmol) and sodium tert-butoxide (3.2g, It 33.6mmol) is added in toluene (50mL), is heated to reflux temperature under nitrogen protection, stir 12h；Then it is cooled to room temperature, Solid is obtained by filtration, solid is dry after washing using water and ethyl alcohol；Recrystallization purification is carried out to crude product using dichloroethanes, is obtained 6.8g compound as white solid 2, yield 60%.Mass spectrum: m/z=1007.5 (M+H+)
The synthesis of compound 3
By bromo- 9, the 9- dimethyl fluorene (15.0g, 54.9mmol) of 2-, 2- aminobphenyl (10.2g, 60.4mmol), three (two BENZYLIDENE ACETONE) two palladiums (1.0g, 1.1mmol), 2- dicyclohexyl phosphorus -2,4,6- tri isopropyl biphenyl (1.0g, 2.2mmol) with And sodium tert-butoxide (7.9g, 82.4mmol) is added in toluene (200mL), is heated to reflux temperature under nitrogen protection, stirs 5h； It is then cooled to room temperature, using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column, decompression removes reaction solution Remove solvent；Recrystallization purification is carried out to crude product using methylene chloride/n-heptane system, obtains 11.9g pale brownish solid Intermediate 3-B, yield 60%.
By intermediate 1-A (5.0g, 11.2mmol), 3-B (8.9g, 24.7mmol), tris(dibenzylideneacetone) dipalladium (0.4g, 0.4mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.4g, 0.9mmol) and sodium tert-butoxide (3.2g, It 33.6mmol) is added in toluene (50mL), is heated to reflux temperature under nitrogen protection, stir 16h；Then it is cooled to room temperature, Solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in reaction solution；Use dichloro Methane carries out recrystallization purification to crude product, obtains 5.2g compound as white solid 3, yield 46%.Mass spectrum: m/z=1007.5 (M+H+)
The synthesis of compound 4
1,3- adamantane glycol (5.0g, 29.7mmol) and 2 bromo toluene (11.2g, 65.4mmol) are dissolved in methylene chloride In (70mL), under the conditions of 0 DEG C of nitrogen protection, it is slowly added dropwise trifluoromethanesulfonic acid (11.2g, 74.3mmol), after insulated and stirred 8h It is warmed to room temperature, 2mol/L sodium hydrate aqueous solution is added dropwise into reaction solution, so that pH value=7 of reaction solution.Then liquid separation, it is organic It is mutually dry using magnesium sulfate is added after washing, solvent is removed under reduced pressure；Using normal heptane as mobile phase, using silica gel column chromatography to thick It after product are purified, is recrystallized using methylene chloride/n-heptane system, obtains 6.0g white solid intermediate 4-A, yield It is 43%.
By bromobenzene (10g, 63.7mmol), 2- amino -9,9- dimethyl fluorene (14.7g, 70.1mmol), three (dibenzylidenes Acetone) two palladiums (1.2g, 1.3mmol), 2- dicyclohexyl phosphorus -2,4,6- tri isopropyl biphenyl (1.2g, 2.5mmol) and tertiary fourth Sodium alkoxide (9.2g, 95.5mmol) is added in toluene (150mL), and reflux temperature is heated under nitrogen protection, stirs 2h；Then cool down To room temperature, solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in reaction solution； Recrystallization purification is carried out to crude product using methylene chloride/ethanol system, obtains 14.5g white solid intermediate 4-B, yield is 80%.
By intermediate 4-A (6.0g, 12.7mmol), 4-B (7.9g, 27.8mmol), tris(dibenzylideneacetone) dipalladium (0.5g, 0.5mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.4g, 1.0mmol) and sodium tert-butoxide (3.6g, It 38.0mmol) is added in toluene (50mL), is heated to reflux temperature under nitrogen protection, stir 16h；Then it is cooled to room temperature, Solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in reaction solution；Use dichloro Methane/n-heptane system carries out recrystallization purification to crude product, obtains 6.1g compound as white solid 4, yield 55%.Mass spectrum: M/z=883.5 (M+H+)
The synthesis of compound 5
1,3- adamantane glycol (5.0g, 29.7mmol) and 2- bromofluorobenzene (11.4g, 65.4mmol) are dissolved in methylene chloride In (80mL), under the conditions of 0 DEG C of nitrogen protection, it is slowly added dropwise trifluoromethanesulfonic acid (11.2g, 74.3mmol), after insulated and stirred 12h It is warmed to room temperature, 2mol/L sodium hydrate aqueous solution is added dropwise into reaction solution, so that pH value=7 of reaction solution.Then liquid separation, it is organic It is mutually dry using magnesium sulfate is added after washing, solvent is removed under reduced pressure；Use silica gel column chromatography to thick by mobile phase of normal heptane It after product are purified, is recrystallized using methylene chloride/n-heptane system, obtains 8.1g white solid intermediate 5-A, yield It is 57%.
By intermediate 5-A (4.0g, 8.3mmol), 4-B (5.2g, 18.2mmol), tris(dibenzylideneacetone) dipalladium (0.3g, 0.3mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.3g, 0.7mmol) and sodium tert-butoxide (2.4g, It 24.9mmol) is added in toluene (30mL), is heated to reflux temperature under nitrogen protection, stir 12h；Then it is cooled to room temperature, Solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in reaction solution；Use dichloro Ethane carries out recrystallization purification to crude product, obtains 6.1g compound as white solid 5, yield 83%.Mass spectrum: m/z=891.5 (M +H+)
The synthesis of compound 6
1,3- adamantane glycol (5.0g, 29.7mmol) and 4- bromo biphenyl (15.2g, 65.4mmol) are dissolved in methylene chloride In (100mL), under the conditions of 0 DEG C of nitrogen protection, it is slowly added dropwise trifluoromethanesulfonic acid (11.2g, 74.3mmol), after insulated and stirred 4h It is warmed to room temperature, 2mol/L sodium hydrate aqueous solution is added dropwise into reaction solution, so that pH value=7 of reaction solution.Then by reaction solution Solid is obtained by filtration, solid is dry after washing using water and ethyl alcohol, carries out recrystallization purification to solid crude product using methylene chloride, obtains To 7.7g white solid intermediate 6-A, yield 43%.
By 2- bromonaphthalene (15.0g, 72.4mmol), 2-aminotoluene (8.5g, 79.7mmol), three (dibenzalacetones) two Palladium (1.3g, 1.4mmol), 2- dicyclohexyl phosphorus -2,4,6- tri isopropyl biphenyl (1.4g, 2.9mmol) and sodium tert-butoxide (10.4g, 108.7mmol) is added in toluene (200mL), is heated to reflux temperature under nitrogen protection, stirs 3h；Then cool down To room temperature, solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in reaction solution； Recrystallization purification is carried out to crude product using methylene chloride/n-heptane system, obtains 13.1g white solid intermediate 6-B, yield is 78%.
By intermediate 6-A (7.7g, 12.9mmol), 6-B (6.6g, 28.3mmol), tris(dibenzylideneacetone) dipalladium (0.5g, 0.5mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.4g, 1.0mmol) and sodium tert-butoxide (3.7g, It 38.6mmol) is added in toluene (60mL), is heated to reflux temperature under nitrogen protection, stir 20h；Then it is cooled to room temperature, Solid is obtained after reaction solution filtering, is dried after being washed using water and ethyl alcohol；Recrystallization purification then is carried out to crude product using toluene, is obtained To 5.4g compound as white solid 6, yield 46%.Mass spectrum: m/z=903.5 (M+H+)
The synthesis of compound 7
1,3- adamantane glycol (5.0g, 29.7mmol) and 2- bromine dibenzofurans (16.2g, 65.4mmol) are dissolved in two In chloromethanes (100mL), under the conditions of subzero 10 DEG C of nitrogen protections, trifluoromethanesulfonic acid (11.2g, 74.3mmol) is slowly added dropwise, It is warmed to room temperature after insulated and stirred 4h, 2mol/L sodium hydrate aqueous solution is added dropwise into reaction solution, so that pH value=7 of reaction solution, Solid is obtained by filtration, solid is dry after washing using water and ethyl alcohol, carries out recrystallization purification to crude product using methylene chloride, obtains 9.2g white solid intermediate 7-A, yield 49%.
By bromobenzene (10.0g, 63.7mmol), 4- aminobphenyl (11.9g, 70.1mmol), three (dibenzalacetones) two Palladium (1.2g, 1.3mmol), 2- dicyclohexyl phosphorus -2,4,6- tri isopropyl biphenyl (1.2g, 2.5mmol) and sodium tert-butoxide (9.2g, 95.5mmol) is added in toluene (150mL), and reflux temperature is heated under nitrogen protection, stirs 1h；Then it is cooled to room Solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in temperature, reaction solution；It uses Methylene chloride/ethanol system carries out recrystallization purification to crude product, obtains 11.7g light yellow solid intermediate 7-B, and yield is 75%.
By intermediate 7-A (9.2g, 14.7mmol), 7-B (7.9g, 32.3mmol), tris(dibenzylideneacetone) dipalladium (0.5g, 0.6mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.5g, 1.2mmol) and sodium tert-butoxide (4.2g, It 44.1mmol) is added in toluene (80mL), is heated to reflux temperature under nitrogen protection, stir 8h；It is then cooled to room temperature, instead Solid is obtained after answering liquid to filter, is dried after being washed using water and ethyl alcohol；Recrystallization purification then is carried out to crude product using dichloroethanes, Obtain 7.0g compound as white solid 7, yield 50%.Mass spectrum: m/z=955.4 (M+H+)
The synthesis of compound 8
1,3- adamantane glycol (5.0g, 29.7mmol) and 2- bromodiphenylthiophene (xxg, xxmmol) are dissolved in dichloromethane It in alkane (100mL), under the conditions of subzero 10 DEG C of nitrogen protections, is slowly added dropwise trifluoromethanesulfonic acid (11.2g, 74.3mmol), keeps the temperature It is warmed to room temperature after stirring 6h, 2mol/L sodium hydrate aqueous solution is added dropwise into reaction solution, so that pH value=7 of reaction solution, filtering Solid is obtained, solid is dry after washing using water and ethyl alcohol, carries out recrystallization purification to crude product using dichloroethanes, it is white to obtain 7.6g Color solid intermediate 8-A, yield 39%.
By 2 bromo toluene (15.0g, 87.7mmol), aniline (9.0g, 96.5mmol), tris(dibenzylideneacetone) dipalladium (1.6g, 1.8mmol), 2- dicyclohexyl phosphorus -2,4,6- tri isopropyl biphenyl (1.7g, 3.5mmol) and sodium tert-butoxide (12.6g, 131.5mmol) is added in toluene (200mL), is heated to reflux temperature under nitrogen protection, stirs 1h；Then cool down To room temperature, solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in reaction solution； It the use of methylene chloride/normal heptane is after eluent carries out silica gel column chromatography purification to crude product, to be recrystallized, obtained using ethyl alcohol To 10.2g pale brownish solid Intermediate 8-B, yield 63%.
By intermediate 8-A (7.6g, 11.5mmol), 8-B (4.7g, 25.4mmol), tris(dibenzylideneacetone) dipalladium (0.4g, 0.5mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.4g, 0.9mmol) and sodium tert-butoxide (3.3g, It 34.6mmol) is added in toluene (60mL), is heated to reflux temperature under nitrogen protection, stir 12h；Then it is cooled to room temperature, Solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in reaction solution；Use dichloro Methane/n-heptane system carries out recrystallization purification to crude product, obtains 4.7g compound as white solid 8, yield 47%.Mass spectrum: M/z=863.4 (M+H+)
The synthesis of compound 9
1,3- adamantane glycol (5.0g, 29.7mmol) and 2- bromonaphthalene (13.5g, 65.4mmol) are dissolved in methylene chloride In (80mL), under the conditions of subzero 20 DEG C of nitrogen protections, trifluoromethanesulfonic acid (11.2g, 74.3mmol), insulated and stirred is slowly added dropwise It is warmed to room temperature after 4h, 2mol/L sodium hydrate aqueous solution is added dropwise into reaction solution, so that pH value=7 of reaction solution, are obtained by filtration Solid, solid is dry after being washed using water and ethyl alcohol, carries out recrystallization purification to crude product using methylene chloride, and it is solid to obtain 6.9g white Body intermediate 9-A, yield 42%.
By 2 bromo toluene (10.0g, 58.5mmol), 4- aminobphenyl (10.9g, 64.3mmol), three (dibenzylidenes third Ketone) two palladiums (1.1g, 1.2mmol), 2- dicyclohexyl phosphorus -2,4,6- tri isopropyl biphenyl (1.1g, 2.3mmol) and the tert-butyl alcohol Sodium (8.4g, 87.7mmol) is added in toluene (150mL), is heated to reflux temperature under nitrogen protection, stirs 2h；Then cool down To room temperature, solid is obtained after reaction solution filtering, is dried after being washed using water and ethyl alcohol；Then crude product is recrystallized using toluene Purification, obtains 7.0g compound as white solid 9, yield 50%.
By intermediate 9-A (6.9g, xxmmol), 9-B (7.2g, 27.8mmol), tris(dibenzylideneacetone) dipalladium (0.5g, 0.5mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.4g, 1.0mmol) and sodium tert-butoxide (3.6g, It 37.9mmol) is added in toluene (60mL), is heated to reflux temperature under nitrogen protection, stir 16h；Then it is cooled to room temperature, Solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in reaction solution；Use dichloro Ethane system carries out recrystallization purification to crude product, obtains 6.1g compound as white solid 9, yield 53%.Mass spectrum: m/z=903.5 (M+H+)
The synthesis of compound 10
1,3- adamantane glycol (5.0g, 29.7mmol) and the bromo- 9,9- dimethyl fluorene (17.9g, 65.4mmol) of 2- is molten In methylene chloride (100mL), under the conditions of subzero 10 DEG C of nitrogen protections, be slowly added dropwise trifluoromethanesulfonic acid (11.2g, 74.3mmol), it is warmed to room temperature after insulated and stirred 4h, 2mol/L sodium hydrate aqueous solution is added dropwise into reaction solution, so that reaction solution PH value=7.Then liquid separation, organic phase is dry using magnesium sulfate is added after washing, and solvent is removed under reduced pressure；It is flowing with normal heptane Phase after being purified using silica gel column chromatography to crude product, is recrystallized using methylene chloride/n-heptane system, is obtained 8.9g white solid intermediate 10-A, yield 44%.
By intermediate 10-A (8.9g, 13.1mmol), diphenylamines (4.9g, 29mmol), tris(dibenzylideneacetone) dipalladium (0.5g, 0.5mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.4g, 1.0mmol) and sodium tert-butoxide (3.8g, It 39.3mmol) is added in toluene (70mL), is heated to reflux temperature under nitrogen protection, stir 6h；It is then cooled to room temperature, instead It answers liquid using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column, solvent is removed under reduced pressure；Use toluene pair Crude product carries out recrystallization purification, obtains 6.9g compound as white solid 10, yield 62%.Mass spectrum: m/z=855.5 (M+H+)
Embodiment 1: production organic electroluminescence device
Anode is prepared by following procedure: will be with a thickness ofIto substrate (healthy and free from worry manufacture) be cut into 40mm × The size of 40mm × 0.7mm is prepared into the experiment base with cathode, anode and insulating layer pattern using photo-mask process Plate utilizes UV ozone and O2:N2Plasma is surface-treated, with increase anode (experimental substrate) work function and it is clear Except dross.
On experimental substrate (anode) vacuum evaporation m-MTDATA with formed with a thickness of hole injection layer (HIL), and On hole injection layer vacuum evaporation compound 1 with formed with a thickness ofHole transmission layer (HTL).
Be deposited TCTA on the hole transport layer, formed with a thickness ofElectronic barrier layer (EBL).
It regard α, β-AND as main body, while adulterating 4,4'- (3,8- bis- (N, the N- diphenyl benzenes of diphenyl pyrene -1,6- diyl Amine), form with a thickness ofLuminescent layer (EML).
DBimiBphen and LiQ is mixed and is deposited with the weight ratio of 1:1 and is formdThick electron transport Layer (ETL), by LiQ vapor deposition on the electron transport layer with formed with a thickness ofElectron injecting layer (EIL), then by magnesium (Mg) Mixed with silver-colored (Ag) with the ratio of 9:1, vacuum evaporation on electron injecting layer, formed with a thickness ofCathode.
In addition, as N- (4- (9H- carbazole -9- base) the phenyl) -4'- being deposited with a thickness of 65nm on above-mentioned cathode (9H- carbazole -9- base)-N- phenyl-[1,1'- biphenyl] -4- amine is formed coating (CPL), to complete organic luminescent device Manufacture.
Embodiment 2-10
Other than respectively using compound shown in table 1 when forming hole transmission layer, utilization is same as Example 1 Method make organic electroluminescence device.
I.e. embodiment 2 makes organic electroluminescence device using compound 2, and embodiment 3 makes Organic Electricity using compound 3 Corresponding compound 4-10 production organic electroluminescence device is respectively adopted in electroluminescence device, embodiment 4-10, and device performance is shown in Table 1.
1~comparative example of comparative example 3
In the embodiment 1, in addition to having used NPB, compound A and compound B as hole transporting layer substitutionization It closes except object 1, manufactures organic electroluminescence device with method same as Example 1.
I.e. comparative example 1 manufactures organic electroluminescence device using NPB, and comparative example 2 is using compound A manufacture organic electroluminescence hair Optical device, comparative example 3 manufacture organic electroluminescence device using compound B, and device performance is shown in Table 1.
To organic electroluminescence device prepared above, in 10mA/cm2Under conditions of analyze the performance of device, knot Fruit is shown in the following table 1.
1 device performance of table
Embodiment Compound V lm/W Cd/A Cd/m2 Color EQE (%) T50(hr)
1 Compound 1 3.95 5.7 7.1 772.3 Blue 14.4 3000
2 Compound 2 3.90 6 7.4 745.2 Blue 14.7 3050
3 Compound 3 3.88 6.1 7.5 758.9 Blue 14.9 2900
4 Compound 4 3.89 5.5 6.9 751.8 Blue 13.8 3300
5 Compound 5 3.89 6.2 7.7 724.5 Blue 14.9 2900
6 Compound 6 3.88 5.3 6.9 728.4 Blue 13.3 3400
7 Compound 7 3.89 5.4 7.0 734.7 Blue 13.8 3100
8 Compound 8 3.89 6 7.4 717.7 Blue 14.4 3000
9 Compound 9 3.87 5.2 6.4 730.1 Blue 13.1 3400
10 Compound 10 3.90 6 7.4 732.4 Blue 14.7 2980
Comparative example 1 NPB 4.00 5.6 6.5 549 Blue 6.9 1650
Comparative example 2 Compound A 4.10 6.0 6.7 627 Blue 10.9 2600
Comparative example 3 Compound B 3.91 5.7 6.8 665.5 Blue 10.9 2850
Reference table 1, in the case that the compound of the present invention is used as hole transporting layer by embodiment 1-10, with comparative example 1-3 Compound compare, voltage (V), current efficiency (Cd/A), brightness (Cd/m2) and external quantum efficiency (EQE) and half-life (T50) better characteristics is showed.Therefore, the device made using the compounds of this invention, having reduces driving voltage, improves Luminous efficiency and the characteristic to prolong the service life.
In conclusion the compounds of this invention to be used as to the hole transmission layer of organic electroluminescence device, so that including the change The organic electroluminescence device for closing object has lower driving voltage, higher luminous efficiency and better service life.
According to the table 1 of the result of the organic electroluminescent device of the embodiment it is found that the compound of the present invention is in bis- (three virtues Base amine) on the basis of symmetrical structure, adamantane is introduced as new core group, changes molecular conformation, reduction finishes The symmetry of structure.When being used as hole transporting material, the hole transport performance of material can be further promoted.It therefore, can be with Manufacture the organic electroluminescence device with excellent characteristics such as driving voltage, luminous efficiency, external quantum efficiency and half-life.
Above embodiments are the further explanation to the compound of the present invention, and range is claimed simultaneously in invention of the invention It is not limited to this.For those skilled in the art, remembered not departing to invent in claimed range Under the range of the technical idea of the invention carried, the various supplements and deformation carry out to the present invention also belong to protection model of the invention It encloses.

Claims (9)

1. a kind of electroluminescent organic material, which is characterized in that the structural formula of the material as described in chemical formula 1:
Ar1、Ar2、Ar5With Ar6Alkane that is identical or different, being separately 1-20 selected from substituted or unsubstituted carbon atom number Alkynyl that alkenyl that base, substituted or unsubstituted carbon atom number are 2-20, substituted or unsubstituted carbon atom number are 2-24 replaces Or unsubstituted carbon atom number be 3-20 naphthenic base, substituted or unsubstituted carbon atom number be 2-20 Heterocyclylalkyl, replace Or unsubstituted carbon atom number be 7-30 aralkyl, substituted or unsubstituted carbon atom number be 2-30 heteroarylalkyl, replace Or unsubstituted carbon atom number be 6-30 aryl, substituted or unsubstituted carbon atom number be one of heteroaryl of 1-30；
Ar3And Ar4It is identical or different, separately selected from singly-bound, the alkylene that substituted or unsubstituted carbon atom number is 1-20 Alkynylene that alkenylene that base, substituted or unsubstituted carbon atom number are 2-20, substituted or unsubstituted carbon atom number are 2-24, The heterocycle alkylene that ring alkylidene that substituted or unsubstituted carbon atom number is 3-20, substituted or unsubstituted carbon atom number are 2-20 The miscellaneous Asia that sub- aralkyl that base, substituted or unsubstituted carbon atom number are 7-30, substituted or unsubstituted carbon atom number are 2-30 Arlydene that aralkyl, substituted or unsubstituted carbon atom number are 6-30, substituted or unsubstituted carbon atom number are the miscellaneous of 1-30 The miscellaneous Asia of arlydene, the ring alkenylene of substituted or unsubstituted carbon atom number 3-15, substituted or unsubstituted carbon atom number 2-15 One of alkenyl, miscellaneous alkynylene of substituted or unsubstituted carbon atom number 2-15.
2. electroluminescent organic material according to claim 1, which is characterized in that the Ar1、Ar2、Ar3、Ar4、Ar5And Ar6Substituent group it is identical or different, and separately be selected from deuterium, cyano, nitro, halogen, hydroxyl, substituted or unsubstituted carbon The alkyl of atomicity 1-20, the naphthenic base of substituted or unsubstituted carbon atom number 3-20, substituted or unsubstituted carbon atom number 2- 20 alkenyl, the alkynyl of substituted or unsubstituted carbon atom number 2-24, substituted or unsubstituted carbon atom number 2-20 heterocycle alkane Base, the aralkyl of substituted or unsubstituted carbon atom number 7-20, substituted or unsubstituted carbon atom number 2-20 heteroarylalkyl, take The aryl of generation or unsubstituted carbon atom number 6-20, the heteroaryl of substituted or unsubstituted carbon atom number 1-20, substitution do not take It is the alkoxy of the carbon atom number 1-20 in generation, the alkylthio group that substituted or unsubstituted carbon atom number is 1-20, substituted or unsubstituted The alkylamino of carbon atom number 1-20, the fragrant amino of substituted or unsubstituted carbon atom number 6-20, substituted or unsubstituted carbon atom Number the heteroaryl amino of 1-20, the arylalkylamino of substituted or unsubstituted carbon atom number 7-20, substituted or unsubstituted carbon atom number The arylsilyl groups, substituted or unsubstituted for being 6-24 for the aIkylsilyl groups of 1-20, substituted or unsubstituted carbon atom number Carbon atom number be 6-20 aryloxy group, substituted or unsubstituted carbon atom number be one of 6-20 arylthio.
3. electroluminescent organic material according to claim 1, which is characterized in that the Ar1、Ar2、Ar5With Ar6It is identical Or it is different, it is separately former selected from the aralkyl, substituted or unsubstituted carbon that substituted or unsubstituted carbon atom number is 7-30 Aryl that heteroarylalkyl that subnumber is 2-30, substituted or unsubstituted carbon atom number are 6-30, substituted or unsubstituted carbon atom Number is one of the heteroaryl of 1-30.
4. electroluminescent organic material according to claim 1, which is characterized in that the Ar3、Ar4It does not take selected from substitution or Heteroarylidene that arlydene that the carbon atom number in generation is 6-30, substituted or unsubstituted carbon atom number are 1-30 replaces or does not take Sub- aralkyl that the carbon atom number in generation is 7-30, substituted or unsubstituted carbon atom number are one in the miscellaneous sub- aralkyl of 2-30 Kind.
5. electroluminescent organic material according to claim 1, which is characterized in that the chemical formula 1 is as in flowering structure One kind:
6. electroluminescent organic material according to claim 1, which is characterized in that the Ar3、Ar4It does not take selected from substitution or The phenyl in generation, substituted or unsubstituted xenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthalene, substitution Or in unsubstituted dimethyl fluorenyl, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene One kind.
7. a kind of organic electroluminescence device, have including cathode, anode and one layer or more between the cathode and anode Machine layer, which is characterized in that at least one layer of comprising described in claim 1 in one layer or more organic layer between the cathode and anode Electroluminescent material.
8. organic electroluminescence device according to claim 7, which is characterized in that the organic layer includes hole injection Layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer.
9. organic electroluminescence device according to claim 7, which is characterized in that comprising described in claim 1 electroluminescent The organic matter layer of luminescent material is hole transmission layer.
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CN112209840B (en) * 2020-03-13 2022-01-28 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, electronic component, and electronic device
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