CN109509845A - A kind of organic electroluminescence device combined material and its organic electroluminescence device - Google Patents

A kind of organic electroluminescence device combined material and its organic electroluminescence device Download PDF

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CN109509845A
CN109509845A CN201811540738.1A CN201811540738A CN109509845A CN 109509845 A CN109509845 A CN 109509845A CN 201811540738 A CN201811540738 A CN 201811540738A CN 109509845 A CN109509845 A CN 109509845A
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electroluminescence device
organic electroluminescence
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蔡辉
董秀芹
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The present invention provides a kind of organic electroluminescence device combined material and its organic electroluminescence device, is related to organic optoelectronic materials technology.The present invention is by containing carbazole and 3, axis vinyl compound is adulterated in the arylamine class host material of 5- diphenyl benzene group obtains a kind of organic electroluminescent combined material, it has good electric conductivity and cavity transmission ability, it is easy to form a film, it is not easy to crystallize, thermal stability is good, applied in organic electroluminescence device be used as hole injection layer, it can effectively reduce organic electroluminescence device driving voltage, improve the luminous efficiency of device, it is high to solve existing organic electroluminescence device driving voltage, the high problem of energy consumption.

Description

A kind of organic electroluminescence device combined material and its organic electroluminescence device
Technical field
The present invention relates to organic photoelectrical material technical field more particularly to a kind of organic electroluminescence device combined materials And its organic electroluminescence device.
Background technique
Organic electroluminescent is the phenomenon to shine under electric current or electric field action in luminous organic material, utilizes this principle system Electric energy can be converted into luminous energy by standby organic electroluminescence device, with self-luminous, visual angle is wide, fast response time, Color is true to nature, clarity is high, high-luminous-efficiency, operation voltage is low, plate thickness is thin, can make large scale and flexible panel And the simply equal outstanding advantages of production process, become domestic and international popular emerging FPD industry.
Organic electroluminescence device generally uses laminar structure, and typical organic electroluminescence device structure is to generally comprise Cathode, anode and the organic matter layer between electrode.It is organic used in organic matter layer applied to organic electroluminescence device Photoelectric material can be roughly divided into two class materials: charge injection and transport layer, luminescent material from purposes.Wherein, charge injection passes Defeated material is divided into hole-injecting material, hole mobile material, electron injection material, electron transport material, and effect is mainly flat The carrier that weighs injects, so that electronics is effectively combined to form exciton with hole in luminescent layer, and then is shone, improves luminous efficiency.
Currently, the research of electroluminescent organic material is carried out in academia and industry extensively, a large amount of function admirables Electroluminescent organic material be developed successively, all in all, the direction of the following OLED be develop high efficiency, high brightness, Long-life, inexpensive white light parts and full color display device, but the technological industrialization process still faces many keys and asks How topic reduces carrier injection barrier, improves carrier injection and migration rate, equilbrium carrier injection, and then reduce device The driving voltage of part reduces energy consumption, improves luminous efficiency, and extending device service life etc. becomes urgent problem to be solved.
Summary of the invention
The object of the present invention is to provide a kind of organic electroluminescence device combined material and its organic electroluminescence device, A kind of organic electroluminescence device provided by the invention combined material has the injection of good hole and transmittability, conductivity Height, stability is good, and good film-forming property, synthetic method is simple to operation, which is applied to combined material Device drive voltage can be effectively reduced as hole injection layer in organic electroluminescence device, improves device light emitting efficiency, reduces Energy consumption.
The present invention provides a kind of organic electroluminescence device combined material, which contains host material and mixes Miscellaneous material, wherein any one of host material in chemical formula I, II:
Wherein, Ar1、Ar2Independently selected from substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C30 Any one in aryl, substituted or unsubstituted C3~C30 heteroaryl；R1、R2、R3、R4Independently selected from H, deuterium, substitution or Unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C30 aryl, takes substituted or unsubstituted C1~C10 alkylene Generation or unsubstituted C6~C30 aryl amine, substituted or unsubstituted C6~C30 aralkyl, substituted or unsubstituted C6~C30 virtue Sulfenyl, substituted or unsubstituted C6~C30 aryloxy group, any one in substituted or unsubstituted C3~C30 heteroaryl, a, b, C, d independently selected from 0 to 5 integer, when independently value is greater than 1 by a, b, c, d, corresponding multiple R1It can be selected from different bases Group, corresponding multiple R2It can be selected from different groups, corresponding multiple R3It can be selected from different groups, corresponding multiple R4It is optional From different groups, multiple R1Between, multiple R2Between, multiple R3Between, multiple R4Between can be independently connected cyclization；
Wherein dopant material is Radialene compounds, and molecular structural formula is as shown in chemical formula III:
Wherein, R5、R6、R7Independently selected from CN, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3 Any one in the heteroaryl of~C30, the substituent group is independently selected from any one in cyano, halogen, trifluoromethyl Kind.
Preferably, any one of host material in chemical formula IV, V:
Preferably, R1、R2、R3、R4It does not take independently selected from H, deuterium, substituted or unsubstituted C1~C10 alkyl, substitution or C1~C10 alkene in generation, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C6~C30 aryl amine, replace or Any one in unsubstituted C3~C30 heteroaryl.
Further preferably, R1、R2、R3、R4Independently selected from H, deuterium, methyl, ethyl, isopropyl, tert-butyl, sec-butyl, substitution or Unsubstituted following group: phenyl, naphthalene, anthryl, phenanthryl, acridinyl, fluorenyl, Spirofluorene-based, carbazyl, furyl, thienyl, Benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophene, pyridyl group, pyrimidine radicals, triazine radical, quinolyl, Isoquinolyl, pyridazinyl, pyrazinyl, quinoxalinyl, quinazolyl, indyl, azepine carbazyl, phenoxazine base, phenoxazine thiophene base, Phenothiazinyl, imidazole radicals, benzimidazolyl, any one in diphenyl amido.
Further preferably, Ar1、Ar2Independently selected from substituted or unsubstituted following group: phenyl, naphthalene, anthryl, phenanthryl, three Phenylene, pyrenyl, base, acridinyl, fluorenyl, Spirofluorene-based, carbazyl, furyl, thienyl, benzofuranyl, benzothiophene Base, dibenzofuran group, dibenzothiophene, pyridyl group, pyrimidine radicals, triazine radical, quinolyl, isoquinolyl, pyridazinyl, pyrazine Base, quinoxalinyl, quinazolyl, indyl, azepine carbazyl, phenoxazine base, phenoxazine thiophene base, phenothiazinyl, imidazole radicals, benzo Any one in imidazole radicals, naphtho- imidazoles, phenanthro- imidazoles, pyrene and imidazole radicals.
Further preferably, R5、R6、R7Independently selected from any one in group as follows:
Wherein, X1、X2、X3、X4、X5、X6、X7、X8、X9Independently selected from halogen, cyano, trifluoromethyl, substituted or unsubstituted C1~C6 alkyl, substituted or unsubstituted C6~C12 aryl, any one in substituted or unsubstituted C3~C12 heteroaryl Kind, wherein substituent group is independently selected from any one in halogen, cyano, trifluoromethyl.
Most preferably, a kind of host material of organic electroluminescence device combined material of the present invention is selected from following knot Any one in structure:
Most preferably, any one of the dopant material in such as flowering structure:
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device successively include cathode, Organic matter layer, anode, it is at least one layer of in the organic matter layer to contain organic electroluminescence device of the present invention combination Material.
Preferably, organic matter layer of the present invention includes hole injection layer, and institute of the present invention is contained in the hole injection layer Any organic electroluminescence device combined material stated.
Beneficial effects of the present invention:
The present invention provides a kind of organic electroluminescence device combined material and its organic electroluminescence device.The present invention is logical Cross axis vinyl compound shown in doped compound II in the arylamine class host material shown in chemical compounds I obtain it is of the present invention Organic electroluminescence device combined material.Chemical compounds I host material of the present invention has both carbazole structure and 3,5- bis- Phenyl group, foring the biggish multichain dendritic morphology of steric configuration conducive to the transmission in hole reduces the coplanar of molecule Property, it is easy to form a film, molecular weight is larger, glass transition temperature with higher, is not easy to crystallize, and is easy to form a film.
The aryl and heterocycle that there is compound ii doped compound of the present invention cyano, halogen, trifluoromethyl to replace The electron accepting groups such as base, itself has stronger electron affinity, these electron acceptor molecules pass through in chemical compounds I matrix material Electron transmission in material generates so-called hole, realizes the generation and transmitting in hole, a kind of organic electroluminescence hair of the present invention Optical device has good electric conductivity and hole transport performance with combined material.
It, will since organic electroluminescence device combined material of the present invention is conductive and hole transport performance Organic electroluminescence device of the present invention uses combined material to be applied in organic electroluminescence device as hole injection layer, The injection barrier that can effectively reduce device anode side hole reduces the driving voltage of device, improves injection rate and the migration in hole Rate, and then improve carrier and improved in the compound quantity and recombination probability of luminescent layer, so that luminous efficiency with higher, reduces Energy consumption.
Organic electroluminescence device of the present invention combined material mesostroma material glass transition temperature with higher And film forming, the stability of device can be effectively improved.
Had using organic electroluminescence device prepared by organic electroluminescence device combined material of the present invention The beneficial effect that driving voltage is low, luminous efficiency is high, low energy consumption.
Specific embodiment:
It is clearly and completely described below in conjunction with the technical solution of the embodiment of the present invention, it is clear that described implementation Example is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, art technology Personnel's every other embodiment obtained without making creative work, belongs to protection scope of the present invention.
Alkyl of the present invention refers to alkyl made of minusing a hydrogen atom in alkane molecule, can be straight chain alkane Base, branched alkyl, naphthenic base, example may include methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary fourth Base, amyl, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Aryl of the present invention refers to remove a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule after, be left the total of univalent perssad Claiming, can be monocyclic aryl or fused ring aryl, example may include phenyl, xenyl, naphthalene, anthryl, phenanthryl or pyrenyl etc., but It is without being limited thereto.
Heteroaryl of the present invention be the heteroaromatic being made of carbon and hetero atom core carbon on remove a hydrogen atom, be left The general name of univalent perssad, the hetero atom include but is not limited to oxygen, sulphur, nitrogen-atoms, and the heterocycle can be monocyclic heterocycles base Or fused ring heterocycle base, example may include pyridyl group, pyrimidine radicals, triazine radical, indyl, quinolyl, isoquinolyl, benzothiophene Base, benzofuranyl, dibenzofuran group, dibenzothiophene, carbazyl etc., but not limited to this.
The present invention provides a kind of organic electroluminescence device combined material, which contains host material and mixes Miscellaneous material, wherein any one of host material in chemical formula I, II:
Wherein, Ar1、Ar2Independently selected from substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C30 Any one in aryl, substituted or unsubstituted C3~C30 heteroaryl；R1、R2、R3、R4Independently selected from H, deuterium, substitution or Unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C30 aryl, takes substituted or unsubstituted C1~C10 alkylene Generation or unsubstituted C6~C30 aryl amine, substituted or unsubstituted C6~C30 aralkyl, substituted or unsubstituted C6~C30 virtue Sulfenyl, substituted or unsubstituted C6~C30 aryloxy group, any one in substituted or unsubstituted C3~C30 heteroaryl, a, b, C, d independently selected from 0 to 5 integer, when independently value is greater than 1 by a, b, c, d, corresponding multiple R1It can be selected from different bases Group, corresponding multiple R2It can be selected from different groups, corresponding multiple R3It can be selected from different groups, corresponding multiple R4It is optional From different groups, multiple R1Between, multiple R2Between, multiple R3Between, multiple R4Between can be independently connected cyclization；
According to the present invention, the substituted alkyl, substituted aryl, substituted heteroaryl, substituted aryl amine, replace Aralkyl, substituted alkylene, substituted arylthio, substituted aryloxy group, wherein the substituent group is independently selected from deuterium, cyanogen Base, halogen, C1~C10 alkyl, C6~C24 aryl, C6~C24 aryl amine or C3~C24 heteroaryl, preferably deuterium, methyl, second Base, propyl, isopropyl, tert-butyl, phenyl, naphthalene, xenyl, phenanthryl, anthryl, triphenylene, carbazyl, furyl, thiophene Base, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophene, acridinyl, phenoxazine base, phenothiazinyl, It is 9,9-dimethylacridan base, fluorenyl, 9,9- dimethyl fluorenyl, pyridyl group, pyrimidine radicals, triazine radical, any in diphenyl amido It is a kind of.
Wherein dopant material is Radialene compounds, and molecular structural formula is as shown in chemical formula III:
Wherein, R5、R6、R7Independently selected from CN, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3 Any one in the heteroaryl of~C30, the substituent group is independently selected from any one in cyano, halogen, trifluoromethyl Kind.
Preferably, any one of host material in chemical formula IV, V:
Preferably, R1、R2、R3、R4It does not take independently selected from H, deuterium, substituted or unsubstituted C1~C10 alkyl, substitution or C1~C10 alkene in generation, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C6~C30 aryl amine, replace or Any one in unsubstituted C3~C30 heteroaryl.
Further preferably, R1、R2、R3、R4Independently selected from H, deuterium, methyl, ethyl, isopropyl, tert-butyl, sec-butyl, substitution or Unsubstituted following group: phenyl, naphthalene, anthryl, phenanthryl, acridinyl, fluorenyl, Spirofluorene-based, carbazyl, furyl, thienyl, Benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophene, pyridyl group, pyrimidine radicals, triazine radical, quinolyl, Isoquinolyl, pyridazinyl, pyrazinyl, quinoxalinyl, quinazolyl, indyl, azepine carbazyl, phenoxazine base, phenoxazine thiophene base, Phenothiazinyl, imidazole radicals, benzimidazolyl, any one in diphenyl amido.
Further preferably, Ar1、Ar2Independently selected from substituted or unsubstituted following group: phenyl, naphthalene, anthryl, phenanthryl, three Phenylene, pyrenyl, base, acridinyl, fluorenyl, Spirofluorene-based, carbazyl, furyl, thienyl, benzofuranyl, benzothiophene Base, dibenzofuran group, dibenzothiophene, pyridyl group, pyrimidine radicals, triazine radical, quinolyl, isoquinolyl, pyridazinyl, pyrazine Base, quinoxalinyl, quinazolyl, indyl, azepine carbazyl, phenoxazine base, phenoxazine thiophene base, phenothiazinyl, imidazole radicals, benzo Any one in imidazole radicals, naphtho- imidazoles, phenanthro- imidazoles, pyrene and imidazole radicals.
Further preferably, R5、R6、R7Independently selected from any one in group as follows:
Wherein, X1、X2、X3、X4、X5、X6、X7、X8、X9Independently selected from halogen, cyano, trifluoromethyl, substituted or unsubstituted C1~C6 alkyl, substituted or unsubstituted C6~C12 aryl, any one in substituted or unsubstituted C3~C12 heteroaryl Kind, wherein substituent group is independently selected from any one in halogen, cyano, trifluoromethyl.
Most preferably, as an example, it is not particularly limited, a kind of organic electroluminescence device combination material of the present invention Any one of the host material of material in such as flowering structure:
Most preferably, as an example, it is not particularly limited, a kind of organic electroluminescence device combination material of the present invention Any one of the dopant material of material in such as flowering structure:
A kind of host material chemical compounds I of organic electroluminescence device combined material of the invention, synthetic route is such as Under:
1, raw material a-1, a-2, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains intermediate I -1；
2, raw material a-3, a-4, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains intermediate I -2；
3, raw material a-5, intermediate I -2, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains centre Body I -3；
4, intermediate I -3, I -1, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains chemical compounds I.
A kind of host material compound ii of organic electroluminescence device combined material of the invention, synthetic route is such as Under:
1, raw material b-1, b-2, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains intermediate II -1；
2, raw material b-3, b-4, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains intermediate II -2；
3, raw material b-5, intermediate II -2, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains centre Body II -3；
4, intermediate II -3, II -1, with Pd2(dba)3、P(t-Bu)3For catalyst, NaOBu-t is alkali, obtains compound Ⅱ。
A kind of dopant material compound III of organic electroluminescence device combined material of the invention, synthetic route is such as Under:
1, raw material c-1, ethyl cyanoacetate, K2CO3, reaction obtains intermediate c-2 in DMF solution；Intermediate is in acetic acid water Solution, H2SO4Under the conditions of reaction obtain intermediate c-3 when n=6 (for c-3-1 when n=5, when n=6 is c-3-2, be c-3-3)；
2, intermediate c-3-1, c-3-2, tetrachloro cyclopropylene, triethylamine react to obtain intermediate III -1；Intermediate III -1 with C-3-3 reacts to obtain intermediate III -2；Intermediate III -2 and HNO3Reaction obtains compound III.
The present invention limitation not special to above-mentioned reaction be using popular response well-known to those skilled in the art Can, the preparation method is simple, easily operated.
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device successively include cathode, Organic matter layer, anode, it is at least one layer of in the organic matter layer to contain organic electroluminescence device of the present invention combination Material.
Preferably, organic matter layer of the present invention includes hole injection layer, and institute of the present invention is contained in the hole injection layer Any organic electroluminescence device combined material stated.
Organic electroluminescence device structure of the present invention are as follows: ITO is as transparent anode, Organic Electricity of the present invention Electroluminescence device is with combined material compound as hole injection layer, and NPB is as hole transmission layer, CBP/Ir (ppy)3As hair Photosphere substance, BAlq is as hole blocking layer, Alq3As electron transfer layer, LiF is used as cathode as electron injecting layer, Al.
Organic electroluminescence device of the present invention can be widely applied to Display panel, lighting source, flexibility OLED, electronics The fields such as paper, Organophotoreceptor or Organic Thin Film Transistors, direction board, signal lamp.
The synthesis of [embodiment 1] compound 1-1
Step2: 1,1':3', 1 " terphenyl -5'- amine (2.45,10mmol), 3- bromine-N-phenylcarbazole are added in reactor (3.22g, 10mmol), Pd2(dba)3(0.21g, 0.25mmol), P (t-Bu)3(0.18g, 0.84mmol), NaOt-Bu (2.8g, 25mmol), toluene solution 100mL reacts for 24 hours under the conditions of 100 DEG C, organic with ether and water extraction after reaction Phase, organic layer MgSO4Dry, condensed organic crosses column chromatography, is recrystallized to give intermediate 1-1-1 (3.80g, 78%).
Step3: in reactor be added intermediate 1-1-1 (4.87g, 10mmol), the iodo- biphenyl of the bromo- 4- of 4- (3.59g, 10mmol)、Pd2(dba)3(0.21g, 0.25mmol), P (t-Bu)3(0.18g, 0.84mmol), NaOt-Bu (2.8g, 25mmol), toluene solution 100mL reacts for 24 hours under the conditions of 100 DEG C, extracts organic phase with ether and water after reaction, organic Layer uses MgSO4Dry, condensed organic crosses column chromatography, is recrystallized to give intermediate 1-1-2 (5.74g, 80%).
Step4: intermediate 1-1-2 (7.17g, 10mmol), diphenylamines (1.69g, 10mmol), Pd are added in reactor2 (dba)3(0.21g, 0.25mmol), P (t-Bu)3(0.18g, 0.84mmol), NaOt-Bu (2.8g, 25mmol), toluene solution 100mL reacts for 24 hours under the conditions of 100 DEG C, extracts organic phase, organic layer MgSO with ether and water after reaction4It is dry, it is dense Contracting organic matter crosses column chromatography, is recrystallized to give compound 1-1 (6.61g, 82%).
The synthesis of [embodiment 2] compound 1-18
Compound 1-18 (7.19g, 78%) is obtained according to the synthetic method of compound 1-1.
The synthesis of [embodiment 3] compound 1-41
Compound 1-41 (7.46g, 80%) is obtained according to the synthetic method of compound 1-1.
The synthesis of [embodiment 4] compound 1-81
Compound 1-81 (7.02,82%) is obtained according to the synthetic method of compound 1-1.
The synthesis of [embodiment 5] compound 1-111
Compound 1-111 (7.08,79%) is obtained according to the synthetic method of compound 1-1.
The synthesis of [embodiment 6] compound 1-117
Compound 1-117 (7.69g, 79%) is obtained according to the synthetic method of compound 1-1.
The synthesis of [embodiment 7] compound 1-165
Compound 1-165 (6.88g, 78%) is obtained according to the synthetic method of compound 1-1.
The synthesis of [embodiment 8] compound 1-185
Compound 1-185 (6.68g, 78%) is obtained according to the synthetic method of compound 1-1.
The synthesis of [embodiment 9] compound 2-1
Step1: 370mL DMF, 207mmol cyan-acetic ester (being dissolved in 50mL DMF), perfluoro are added in reactor Benzene (38.51g, 207mmol), K2CO3(34.55g, 250mmol), stirs 48h at room temperature, after by reaction suspension and 1L ice water It injects in 3L beaker, in stirring with 100mL spirit acid souring soln, successively uses 250mL, 150mL, 100mL, 100mL CCl4Extraction aqueous solution four times, obtained organic layer is dry with magnesium sulfate, removes solvent in vacuum, obtains intermediate 2-1-1, will Obtained intermediate 2-1-1 all additions, the 4.15mL concentrated sulfuric acid, 84mL acetic acid (50%), are heated to reflux 16h, are cooled to room temperature Afterwards, by mixture and 120mL ice water injection 500mL beaker in, stir 30min, with 100mL chloroform extract, separation organic layer and Water layer, organic layer are washed with the saturated sodium bicarbonate solution of the water of 100mL and 100mL, and obtained organic layer is dry with magnesium sulfate, Solvent is removed in vacuum, rear vacuum distillation obtains intermediate 2-1-2 (36.4g, 85%).
Step2: addition lithium hydride (98%), which is suspended in the 1,2- dimethoxy-ethane of 600mL, in reactor is cooled to 0 ℃.Intermediate 2-1-2 (31.48g, 152mmol) is dissolved in 1, the 2- dimethoxy-ethane of 60mL and is added in 10-15min Add, removes ice bath and heating 45min carries out reaction, stir 15min at room temperature, mixture is cooled to 0 DEG C again, by tetrachloro Cyclopropylene (7.12g, 40mmol) is added dropwise in 1, the 2- dimethoxy-ethane of 40mL, is continued to be stirred to react 44h while is heated to Then room temperature is injected reaction suspension in 2L beaker together with 1.2L ice water, be acidified to the solution in stirring with concentrated hydrochloric acid PH=1, and being extracted with ethyl acetate three times, after the organic layer of mixing is successively washed with salt water, water and bicarbonate solution, then It is washed with water again, organic layer, and removal solvent careful in a vacuum is dried with magnesium sulfate, until generating dark material.Afterwards The HBr (48%) for the 360mL that dark material is dissolved in the acetic acid (100%) of 1400mL, and was prepared before with about ten minutes It is handled with the mixture of 120mL nitric acid (65%), obtained mixture is stirred into 1.5h, mixture is filtered, is washed with water to obtain Organic layer precipitating, and is dried in a vacuum to obtain crude product, it is rear by gradient biochemical purification obtain compound 2-1 (9.38g, 36%).
The synthesis of [embodiment 10] compound 2-3
Compound 2-3 (2.69g, 40%) is obtained according to the synthetic method of compound 2-1.
The synthesis of [embodiment 11] compound 2-5
Step1: intermediate 2-5-1,2-5-2 are obtained according to the synthetic method of the intermediate 2-1-2 in embodiment 9.
Step2: in reactor be added tetrachloro cyclopropylene (8.30g, 46.7mmol), intermediate 2-5-1 (20.0g, 93.4mmol), anhydrous methylene chloride 160mL stirs mixture, is cooled to -30 DEG C, and triethylamine is added dropwise in 30min Mixture is warming to room temperature in 1h, water is added dropwise and filters mixture by (30.7,304mmol), with DCM (3 × 50mL), MeOH (2 × 50mL) and water (4 × 50mL) washing solid are simultaneously dried in a vacuum, and obtain crude product, recrystallize from acetonitrile To intermediate 2-5-3 (19g, 72.8%).
Step3: 2.12 cesium carbonates are added under protection of argon gas, in reactor and are suspended in 45mL anhydrous DMF, and are cooled to 0℃.It is slowly added dropwise into suspension intermediate 2-5-2 (0.80g, 3.95mmol are dissolved in the DMF of 5mL), stirs mixture 5min And add intermediate 2-5-3 (1.74g, 3.1mmol), continue stirring for 24 hours and reaction is made to reach environment temperature, by reaction mixture It imports 250mL to contain in the separatory funnel of 100mL water and 80mL ethyl acetate, organic layer is separated, with 80mL semi-saturation NaCl water Solution washes twice, and is washed twice with 80mL 2M HCL aqueous solution, and washed twice with 80mL saturated sodium bicarbonate aqueous solution, Organic layer is dried with magnesium sulfate afterwards, and by being evaporated in vacuo solvent of carefully going out, obtains intermediate 2-5-4 (2.8g, 115%).
Step4: intermediate 2-5-4 (1.35g, 1.88mmol), 19mL glacial acetic acid are added in reactor, is being vigorously stirred Under, 19mL concentrated nitric acid (65%, w/w) is added dropwise dropwise, after continue to be stirred overnight, after solution be cooled to 0 DEG C and be added dropwise 40mL water is generated with induced precipitation, the mobile phone crude solid product and with 3 × 15mL water washing in sintered frit, in 40 DEG C of temperature Under dry wet crude product 3h in a vacuum drying oven, it is then dry in high vacuum at ambient temperature, produced through dry Object is recrystallized to give compound 2-5 (0.311g, 25%) in 3:2 (v/v) mixture of 1-chlorobutane and hexamethylene.
The FD-MS value for the organic electroluminescence device combined material that the embodiment of the present invention 1~11 synthesizes is as shown in table 1:
[table 1]
Embodiment FD-MS
Embodiment 1 M/z=805.38 (C60H43N3=805.36)
Embodiment 2 M/z=921.43 (C69H51N3=921.41)
Embodiment 3 M/z=931.42 (C70H49N3=931.39)
Embodiment 4 M/z=855.38 (C65H45N3=855.36)
Embodiment 5 M/z=895.37 (C66H45N3O=895.36)
Embodiment 6 M/z=972.44 (C72H52N4=972.42)
Embodiment 7 M/z=881.39 (C66H47N3=881.38)
Embodiment 8 M/z=855.37 (C64H45N3=855.36)
Embodiment 9 M/z=650.98 (C27F15N3=650.99)
Embodiment 10 M/z=672.02 (C30F12N6=672.0)
Embodiment 11 M/z=715.01 (C30F15N5=714.99)
The measurement of conductivity:
[embodiment 12]
Vapor deposition compound 1-1 is mixed in high vacuum chamber on the glass substrate and is used as host material and compound 2-1 and is mixed Miscellaneous material, wherein doping concentration is 3%, film thickness 50nm, and glass substrate has two ITO items of the distance for 1mm as band Type electrode measures vapor deposition membrane conductivity from the I-E characteristic of film.
[embodiment 13]
Host material in embodiment 12 is changed to compound 1-18, measurement vapor deposition membrane conductivity.
[embodiment 14]
Host material in embodiment 12 is changed to compound 1-41, measurement vapor deposition membrane conductivity.
[embodiment 15]
Host material in embodiment 12 is changed to compound 1-81, measurement vapor deposition membrane conductivity.
[embodiment 16]
Host material in embodiment 12 is changed to compound 1-111, measurement vapor deposition membrane conductivity.
[embodiment 17]
Host material in embodiment 12 is changed to compound 1-117, measurement vapor deposition membrane conductivity.
[embodiment 18]
Host material in embodiment 12 is changed to compound 1-165, measurement vapor deposition membrane conductivity.
[embodiment 19]
Host material in embodiment 12 is changed to compound 1-185, measurement vapor deposition membrane conductivity.
[embodiment 20]
Dopant material in embodiment 12 is changed to 2-2, measurement vapor deposition membrane conductivity.
[embodiment 21]
Host material in embodiment 12 is changed to compound 1-18, dopant material is changed to 2-2, measurement evaporation film electricity Conductance.
[embodiment 22]
Host material in embodiment 12 is changed to compound 1-41, dopant material is changed to 2-2, measurement evaporation film electricity Conductance.
[embodiment 23]
Host material in embodiment 12 is changed to compound 1-81, dopant material is changed to 2-2, measurement evaporation film electricity Conductance.
[embodiment 24]
Host material in embodiment 12 is changed to compound 1-111, dopant material is changed to 2-3, measures evaporation film Conductivity.
[embodiment 25]
Host material in embodiment 12 is changed to compound 1-117, dopant material is changed to 2-3, measures evaporation film Conductivity.
[embodiment 26]
Host material in embodiment 12 is changed to compound 1-165, dopant material is changed to 2-3, measures evaporation film Conductivity.
[embodiment 27]
Host material in embodiment 12 is changed to compound 1-185, dopant material is changed to 2-3, measures evaporation film Conductivity.
The conductivity value of the organic electroluminescence device combined material of 12-27 of the embodiment of the present invention is as shown in table 2:
Table 2
[comparative example 1] device prepares embodiment:
Ito glass substrate is placed in distilled water and is cleaned 2 times, it is ultrasonic washing 30 minutes, different after distilled water cleans Ultrasonic washing is later dry in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base Plate washs 5 minutes, is sent in evaporator.
Hole injection layer 2-TNATA/60nm, hole transmission layer are successively deposited on the ito transparent electrode having had been prepared for Compound N PB/60nm, vapor deposition main body CBP: doping Ir (ppy)310% mixing/30nm, hole blocking layer BAlq/10nm, electricity Sub- transport layer Alq3/ 30nm, electron injecting layer LiF/0.2nm, cathode Al/150nm.
[embodiment 28] device prepares embodiment:
The hole injection layer 2-TNATA of comparative example 1 is changed to 1-1:2-1 (97mol%:3mol%).
[embodiment 29] device prepares embodiment:
The hole injection layer 2-TNATA of comparative example 1 is changed to 1-18:2-1 (97mol%:3mol%).
[embodiment 30] device prepares embodiment:
The hole injection layer 2-TNATA of comparative example 1 is changed to 1-41:2-1 (97mol%:3mol%).
[embodiment 31] device prepares embodiment:
The hole injection layer 2-TNATA of comparative example 1 is changed to 1-81:2-1 (97mol%:3mol%).
[embodiment 32] device prepares embodiment:
The hole injection layer 2-TNATA of comparative example 1 is changed to 1-111:2-1 (97mol%:3mol%).
[embodiment 33] device prepares embodiment:
The hole injection layer 2-TNATA of comparative example 1 is changed to 1-117:2-1 (97mol%:3mol%).
[embodiment 34] device prepares embodiment:
The hole injection layer 2-TNATA of comparative example 1 is changed to 1-165:2-1 (97mol%:3mol%).
[embodiment 35] device prepares embodiment:
The hole injection layer 2-TNATA of comparative example 1 is changed to 1-185:2-1 (97mol%:3mol%).
[embodiment 36] device prepares embodiment:
The hole injection layer 2-TNATA of comparative example 1 is changed to 1-1:2-2 (97mol%:3mol%).
[embodiment 37] device prepares embodiment:
The hole injection layer 2-TNATA of comparative example 1 is changed to 1-18:2-2 (97mol%:3mol%).
[embodiment 38] device prepares embodiment:
The hole injection layer 2-TNATA of comparative example 1 is changed to 1-41:2-2 (97mol%:3mol%).
[embodiment 39] device prepares embodiment:
The hole injection layer 2-TNATA of comparative example 1 is changed to 1-81:2-2 (97mol%:3mol%).
[embodiment 40] device prepares embodiment:
The hole injection layer 2-TNATA of comparative example 1 is changed to 1-111:2-3 (97mol%:3mol%).
[embodiment 41] device prepares embodiment:
The hole injection layer 2-TNATA of comparative example 1 is changed to 1-117:2-3 (97mol%:3mol%).
[embodiment 42] device prepares embodiment:
The hole injection layer 2-TNATA of comparative example 1 is changed to 1-165:2-3 (97mol%:3mol%).
[embodiment 43] device prepares embodiment:
The hole injection layer 2-TNATA of comparative example 1 is changed to 1-185:2-3 (97mol%:3mol%).
The characteristics of luminescence test result such as table 3 of luminescent device prepared by 28-43 of the embodiment of the present invention and comparative example 1 It is shown.
[table 3]
The above result shows that a kind of organic electroluminescence device of the invention is applied to organic electroluminescent with combined material In device, especially as hole injection layer, the driving voltage of organic electroluminescence device has apparent reduction, luminous efficiency It increases, can effectively reduce energy consumption, economize on resources.Organic electroluminescence device of the invention is function admirable with combined material Electroluminescent organic material.
It should be pointed out that the present invention is particularly described with individual embodiments, but before not departing from the principle of the invention It puts, ordinary skill people can carry out the improvement on various forms or details to the present invention, these improvement also fall into this hair In bright protection scope.

Claims (10)

1. a kind of organic electroluminescence device combined material, which is characterized in that the combined material contains host material and doping Material, wherein any one of host material in chemical formula I, II:
Wherein, Ar1、Ar2Independently selected from substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C30 aryl, Any one in substituted or unsubstituted C3~C30 heteroaryl；R1、R2、R3、R4Independently selected from H, deuterium, substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C1~C10 alkylene, substituted or unsubstituted C6~C30 aryl, replace or not Substituted C6~C30 aryl amine, substituted or unsubstituted C6~C30 aralkyl, substituted or unsubstituted C6~C30 arylthio, Any one in substituted or unsubstituted C6~C30 aryloxy group, substituted or unsubstituted C3~C30 heteroaryl, a, b, c, d are only It is on the spot selected from 0 to 5 integer, when independently value is greater than 1 by a, b, c, d, corresponding multiple R1It can be selected from different groups, phase The multiple R answered2It can be selected from different groups, corresponding multiple R3It can be selected from different groups, corresponding multiple R4It can be selected from difference Group, multiple R1Between, multiple R2Between, multiple R3Between, multiple R4Between can be independently connected cyclization；
Wherein dopant material is Radialene compounds, and molecular structural formula is as shown in chemical formula III:
Wherein, R5、R6、R7Independently selected from CN, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~ Any one in the heteroaryl of C30, the substituent group is independently selected from any one in cyano, halogen, trifluoromethyl.
2. a kind of organic electroluminescence device combined material according to claim 1, which is characterized in that host material choosing From any one in chemical formula IV, V:
3. a kind of organic electroluminescence device combined material according to claim 1, which is characterized in that R1、R2、R3、R4 It does not take independently selected from H, deuterium, substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C1~C10 alkene, substitution or C6~C30 aryl in generation, substituted or unsubstituted C6~C30 aryl amine, appointing in substituted or unsubstituted C3~C30 heteroaryl It anticipates one kind.
4. a kind of organic electroluminescence device combined material according to claim 1, which is characterized in that R1、R2、R3、R4 Independently selected from H, deuterium, methyl, ethyl, isopropyl, tert-butyl, sec-butyl, substituted or unsubstituted following group: phenyl, naphthalene Base, anthryl, phenanthryl, acridinyl, fluorenyl, Spirofluorene-based, carbazyl, furyl, thienyl, benzofuranyl, benzothienyl, two Benzofuranyl, dibenzothiophene, pyridyl group, pyrimidine radicals, triazine radical, quinolyl, isoquinolyl, pyridazinyl, pyrazinyl, quinoline Quinoline base, quinazolyl, indyl, azepine carbazyl, phenoxazine base, phenoxazine thiophene base, phenothiazinyl, imidazole radicals, benzimidazole Any one in base, diphenyl amido.
5. a kind of organic electroluminescence device combined material according to claim 1, which is characterized in that Ar1、Ar2It is independent Ground is selected from substituted or unsubstituted following group: phenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrenyl, base, acridinyl, fluorenes Base, Spirofluorene-based, carbazyl, furyl, thienyl, benzofuranyl, benzothienyl, dibenzofuran group, dibenzothiophenes Base, pyridyl group, pyrimidine radicals, triazine radical, quinolyl, isoquinolyl, pyridazinyl, pyrazinyl, quinoxalinyl, quinazolyl, indoles Base, azepine carbazyl, phenoxazine base, phenoxazine thiophene base, phenothiazinyl, imidazole radicals, benzimidazolyl, naphtho- imidazoles, phenanthro- imidazoles, Any one in pyrene and imidazole radicals.
6. a kind of organic electroluminescence device combined material according to claim 1, which is characterized in that R5、R6、R7Solely On the spot any one in group as follows:
Wherein, X1、X2、X3、X4、X5、X6、X7、X8、X9Independently selected from halogen, cyano, trifluoromethyl, substituted or unsubstituted C1 ~C6 alkyl, substituted or unsubstituted C6~C12 aryl, any one in substituted or unsubstituted C3~C12 heteroaryl, Middle substituent group is independently selected from any one in halogen, cyano, trifluoromethyl.
7. a kind of organic electroluminescence device combined material according to claim 1, which is characterized in that the matrix material Any one of material in such as flowering structure:
8. a kind of organic electroluminescence device combined material according to claim 1, which is characterized in that the doping material Any one of material in such as flowering structure:
9. a kind of organic electroluminescence device, which is characterized in that the organic electroluminescence device successively includes cathode, organic matter Layer, anode, it is at least one layer of in the organic matter layer to contain organic electroluminescence device according to any one of claims 1 to 8 Use combined material.
10. a kind of organic electroluminescence device according to claim 9, which is characterized in that the organic matter layer includes sky Cave implanted layer contains organic electroluminescence device according to any one of claims 1 to 8 combination material in the hole injection layer Material.
CN201811540738.1A 2018-12-17 2018-12-17 A kind of organic electroluminescence device combined material and its organic electroluminescence device Withdrawn CN109509845A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113372313A (en) * 2021-07-02 2021-09-10 长春海谱润斯科技股份有限公司 Triarylamine compound and organic electroluminescent device thereof
CN113728454A (en) * 2019-04-15 2021-11-30 诺瓦尔德股份有限公司 Compound, organic semiconductor material comprising the compound, organic electronic device comprising the material, and display device and lighting device comprising the organic electronic device

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113728454A (en) * 2019-04-15 2021-11-30 诺瓦尔德股份有限公司 Compound, organic semiconductor material comprising the compound, organic electronic device comprising the material, and display device and lighting device comprising the organic electronic device
CN113372313A (en) * 2021-07-02 2021-09-10 长春海谱润斯科技股份有限公司 Triarylamine compound and organic electroluminescent device thereof

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