CN104119347A - An organic electroluminescence diode material and applications thereof - Google Patents
An organic electroluminescence diode material and applications thereof Download PDFInfo
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- CN104119347A CN104119347A CN201410331388.3A CN201410331388A CN104119347A CN 104119347 A CN104119347 A CN 104119347A CN 201410331388 A CN201410331388 A CN 201410331388A CN 104119347 A CN104119347 A CN 104119347A
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- 239000000463 material Substances 0.000 title claims abstract description 57
- 238000005401 electroluminescence Methods 0.000 title abstract description 46
- 239000002346 layers by function Substances 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 3
- 239000010703 silicon Substances 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims description 78
- 150000001875 compounds Chemical class 0.000 abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 85
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- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 22
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
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- 239000004327 boric acid Substances 0.000 description 10
- 150000003384 small molecules Chemical class 0.000 description 10
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- 125000004799 bromophenyl group Chemical group 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- 0 CCC(C)=C([C@@](C1*2)C(C)=C(*)C(*)=C1C1=C2C(*)=*C(*)C1*)C(CC(C)C=C=N)=C Chemical compound CCC(C)=C([C@@](C1*2)C(C)=C(*)C(*)=C1C1=C2C(*)=*C(*)C1*)C(CC(C)C=C=N)=C 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 230000006837 decompression Effects 0.000 description 4
- 229960000935 dehydrated alcohol Drugs 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
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- 229960004756 ethanol Drugs 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 235000015320 potassium carbonate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000004506 ultrasonic cleaning Methods 0.000 description 3
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
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- 229940125898 compound 5 Drugs 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
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- -1 desolventizing Substances 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
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- 238000002474 experimental method Methods 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000012736 patent blue V Nutrition 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- BMQDAIUNAGXSKR-UHFFFAOYSA-N (3-hydroxy-2,3-dimethylbutan-2-yl)oxyboronic acid Chemical compound CC(C)(O)C(C)(C)OB(O)O BMQDAIUNAGXSKR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
- BCMGOTDNNMLUBS-UHFFFAOYSA-N 2-bromo-1,8-naphthyridine Chemical class C1=CC=NC2=NC(Br)=CC=C21 BCMGOTDNNMLUBS-UHFFFAOYSA-N 0.000 description 1
- KQOOFMWRLDRDAX-UHFFFAOYSA-N 2-chloro-4-fluoro-1-nitrobenzene Chemical class [O-][N+](=O)C1=CC=C(F)C=C1Cl KQOOFMWRLDRDAX-UHFFFAOYSA-N 0.000 description 1
- HNACKJNPFWWEKI-UHFFFAOYSA-N 3,6-dimethyl-9h-carbazole Chemical compound C1=C(C)C=C2C3=CC(C)=CC=C3NC2=C1 HNACKJNPFWWEKI-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- CJVFHPYZIQBJOA-UHFFFAOYSA-N Brc(cc1)cc2c1N1c3c(CCCC4)c4c(CCCC4)c4c3C3C1=CC2=CC3 Chemical compound Brc(cc1)cc2c1N1c3c(CCCC4)c4c(CCCC4)c4c3C3C1=CC2=CC3 CJVFHPYZIQBJOA-UHFFFAOYSA-N 0.000 description 1
- 235000007466 Corylus avellana Nutrition 0.000 description 1
- 240000003211 Corylus maxima Species 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 150000005054 naphthyridines Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
Abstract
The invention relates to an organic electroluminescence diode (OLED) material and applications thereof. The material comprises a compound having a structure of any one of a formula (I), a formula (II) and a formula (III) as follows, wherein R1, R2, and R4-R7 are independently selected from hydrogen, cyano, C1-C40 alkyl, alkoxy, aryl or a silicon-containing substituted group, and R3 is selected from hydrogen, an aromatic ring or a heteroaromatic ring. The material can be used as a functional layer of micromolecule OLED devices, and is applied in the field of organic electroluminescence.
Description
Technical field
The present invention relates to a kind of organic electroluminescent LED (OLED) material, be specifically related to one centered by N atom, and there is the small molecules OLED material of closed-loop structure, and relate to the application of this material in organic electroluminescent field.
Background technology
Organic electroluminescent diode (OLED) results from the eighties in last century, with traditional mesomorphic phase ratio, OLED technique of display, there is luminous, wide viewing angle, fast response time, can realize the plurality of advantages such as flexible demonstration, therefore be considered to likely replace traditional liquid crystal, become the main flow of technique of display of future generation.
According to the difference of used organic materials, OLED device cell can be divided into two kinds of small molecules device and polymer devices, its small molecular device usually has multilayer sandwiched structure, bear respectively different functions for every layer, as hole transmission layer is responsible for transporting holes, luminescent layer is responsible for luminous, and electron transfer layer is responsible for transmission electronic etc., ensureing mutually to mate between each functional layer, is the essential condition of the small molecules device of excellent.
In small molecules device, luminescent layer, in central position, has remarkably influenced for the overall performance of OLED device, and luminescent layer determines the spectrum color of device, and affect efficiency and the life-span of device, in addition, due in OLED device, electric transmission speed is far smaller than hole transport speed, the performance that is electron transport material is usually difficult to match with hole material, therefore, the performance of electron transport material, also has remarkably influenced for device efficiency.
Organic electroluminescent diode (OLED) is from being born so far, the time of existing nearly 30 years, be accompanied by lasting input and the constantly effort of production, teaching & research all circles, nowadays, there are the multiple commodity based on OLED technique of display to realize industrialization, the kind of OLED base mateiral and quantity are also being constantly updated, and particularly the kind of luminescent material and electron transport material and quantity constantly increase.
Summary of the invention
Technical problem to be solved by this invention is, provides a class centered by N atom, and has the organic small molecule material of closed-loop structure, and such material can be used as luminescent material, or as electron transport material, is applied in organic electroluminescence device.
The scheme that the present invention solves the problems of the technologies described above is as follows:
A kind of OLED material, is characterized in that, comprises any one in structure shown in following formula I-formula III:
In formula I～formula III, R1, R2, R4～R7 is independently selected from hydrogen atom, cyano group, the alkyl of C1～C40, alkoxyl group, aromatic base or the substituting group containing element silicon.
R3 is selected from hydrogen atom, contain substituting group or do not contain substituent aromatic nucleus or aromatic heterocycle, and R3 preferentially selects the structure shown in following formula (in formula, A represents the group being connected with R3):
001～the C156 of Compound C shown in following formula, is the representative structure that meets the present invention's spirit and principle, should be appreciated that the concrete structure of listing following compound, just in order to explain better the present invention, is not limitation of the present invention.
An application for OLED material, is characterized in that, this material can be used as luminescent material or electron transport material, is applied in organic electroluminescent field.
The invention has the beneficial effects as follows:
The invention provides a class centered by N atom, and there is the organic small molecule material of closed-loop structure, and the preparation method of such material is provided.Such material can be used as blue emitting material, or is applied in organic electroluminescent field as electron transport material.Using material provided by the invention as functional layer, the organic electroluminescence device of making, has shown good usefulness.
A kind of OLED material of the present invention also has following characteristics:
1. by coupling, Guan Huan, reduces, and the polystep reactions such as iodo, have prepared main points intermediate (intermediate 1-intermediate 6), and based on this, synthesized a class centered by N atom, and had the organic small molecule material of closed-loop structure.
2. such material has stable luminescent properties and good electronic transmission performance, can be used as luminescent material or electron transport material, is applied in organic electroluminescence device.
3. using such material as luminescent layer, the organic electroluminescence device (embodiment 34-embodiment 39) of preparation, CIE coordinate (0.15-0.18,0.14-0.22), for sky blue luminous to mazarine, the maximum current efficiency 0.8-2.6cd/A of device.
4. using such material as luminescent layer, and simultaneously as electron transfer layer, the organic electroluminescence device (embodiment 40-embodiment 43) of preparation, CIE coordinate (0.16-0.18,0.14-0.21), for sky blue luminous to mazarine, the maximum current efficiency 0.48-1.12cd/A of device.
5. using such material as electron transfer layer, using Alq3 as luminescent layer, the organic electroluminescence device of preparation (embodiment 44-embodiment 46), the maximum current efficiency 1.8-2.4cd/A of device.
The preparation method of material described in the present invention is as follows:
First be the preparation of several key intermediates, reaction scheme be shown below (be labeled as the annulus of H1 and H2, represent respectively phenyl ring, hexamethylene ring or pyridine ring):
The 1-of intermediate shown in following formula intermediate 6 makes by above-mentioned route exactly, prepares the specific experiment process of intermediate 1-intermediate 6, refers to hereinafter embodiment 1-embodiment 8.
Further, taking above-mentioned intermediate as raw material, carry out linked reaction respectively from different substrates, obtain target compound, specific experiment process, refers to hereinafter embodiment 9-embodiment 31.
The invention provides a class centered by N atom, and there is the organic small molecule material of closed-loop structure, and the synthetic method of such material is provided,, provide using such material as functional layer meanwhile, be applied to the application example in organic electroluminescence device.
Prepared organic electroluminescence device generally comprises ITO Conducting Glass (anode), hole transmission layer (NPB), luminescent layer (Alq3 or this case material), electron transfer layer (this case material or TPBI), electron injecting layer (LiF) and the cathode layer (Al) of stack successively, and the structural representation of prepared organic electroluminescence device as shown in Figures 1 and 2.All functions layer all adopts vacuum evaporation process to make, and in device, the molecular structural formula of organic compound more used is shown below.
Should be appreciated that described implementation process and result for technician well known in the art, just in order to explain better the present invention, and in order to the operability of this case material to be described, described implementation process is not limitation of the present invention.
The present invention aims to provide a class and can be used as functional layer, be applied to the small molecule material in organic electroluminescent field, the molecular structure having for such small molecule material proposes claim simultaneously, and the application in organic electroluminescent field proposes claim for such material; The present invention also provides the preparation method of such material, due to adopted synthetic route and preparation technology, is mainly to complete with reference to existing document, so for preparation method and the preparation technology of material, have no right requirement; Simultaneously, the present invention also provides using such material as functional layer, be applied to the application example in organic electroluminescence device, described implementation process, there is ubiquity, so, for preparation method and the preparation process of the organic electroluminescence device arriving involved in the present invention, also without any claim.
Brief description of the drawings
Accompanying drawing 1 is structural representation Fig. 1 of prepared organic electroluminescence device, to upper strata, be followed successively by ITO Conducting Glass (101), hole transmission layer (102), luminescent layer (103), electron transfer layer (104), electron injecting layer (105) and cathode layer (106) by lower floor.Wherein luminescent layer (103) or electron transfer layer (104) relate to this case material.
Accompanying drawing 2 is structural representation Fig. 2 of prepared organic electroluminescence device, to upper strata, be followed successively by ITO Conducting Glass (201), hole transmission layer (202), simultaneously as functional layer (203), electron injecting layer (204) and the cathode layer (205) of luminescent layer and electron transfer layer by lower floor.Wherein functional layer (203) relates to this case material.
Embodiment
Below principle of the present invention and feature are described, example, only for explaining the present invention, is not intended to limit scope of the present invention.
Compound Preparation Example:
The preparation of embodiment 1 intermediate 1
Method preparation described in intermediate 1 referenced patent JP2013147481.In 2L there-necked flask, add raw material 1 (53.4g, 0.2mol), chloro-4 fluoronitrobenzenes (35.1g, 0.2mol) of 2-, K
2cO
3(82.8g, 0.6mol), N,N-dimethylacetamide (DMA, 950g), N
2protection, is warming up to 180 DEG C of interior temperature, and insulation reaction 6h, is down to room temperature, adds palladium (5.3g, 0.023mol), tricyclohexyl phosphine a tetrafluoro borate (16.9g, 0.046mol), N in reaction solution
2protection, is warming up to 180 DEG C of interior temperature, insulation reaction 2.5h; by reaction solution slowly in impouring 3.5L deionized water, rapid stirring 30min, suction filtration; 450mL X2 deionized water drip washing filter cake, 300mL cold methanol drip washing filter cake, collects filter cake; add 1.5LTHF to dissolve, gained solution by 180g silicagel column, is sloughed solvent fast; it is solvent recrystallization that thick product uses Virahol, obtains compound 2, gross weight 55.7g; yield 72.1%, MS (m/s): 386.1.
Collect compound 2 (55.7g, 0.144mol), add THF (1100g), room temperature is dissolved, above solution is added in high-pressure hydrogenation still, add palladium carbon 5.0g, airtight hydrogenation still, shortening, hydrogenation pressure 1.5MPa, hydrogenation temperature 60-65 DEG C, reaction times 10h, collect reaction solution, filter, filtrate, by 120g silicagel column, is sloughed solvent, taking toluene: dehydrated alcohol=1:2 (W/W) as solvent, recrystallization, obtains compound 3, filbert solid 40.2g, yield 78.3%, MS (m/s): 356.1.
In 2L there-necked flask, add compound 3 (40.2g, 0.11mol), acetonitrile (428g), deionized water (75g), concentrated hydrochloric acid (34.5g, 0.33mol), N
2protection, is cooled to Nei Wen-5 DEG C, by NaNO
2(8.3g, 0.12mol) is dissolved in 45g deionized water, splashes into reaction flask, about 10min dropwises, and-5 DEG C of insulation reaction 1h, obtain diazonium salt, KI (21.9g, 0.13mol) is dissolved in 50g deionized water, slowly splashes in diazonium salt, about 1h dropwises, and-5 DEG C of insulation 1h, are then warming up to interior temperature 55-60 DEG C, insulation reaction 4h, be down to room temperature, add toluene (500mL), NaHSO
3(20g, 0.19mol), stirs 10min, separatory, 200mL toluene aqueous phase extracted 1 time, merges organic phase, 100mLX3 deionized water wash organic phase, desolventizing, crude product is taking hexanaphthene as eluent, cross purification by silica gel column chromatography, further taking toluene: dehydrated alcohol=1:2 (W/W) is solvent recrystallization, obtains intermediate 1, be the crystal 42.7g of pink colour slightly, yield 83.2%, MS (m/s): 467.0.
The preparation of embodiment 2 intermediates 2
In 1L there-necked flask, add intermediate 1 (21.3g, 0.045mol), duplex pinacol borate (13.7g, 0.054mol), two (diphenylphosphine) ferrocene Palladous chloride (0.33g of 1,2'-, 0.45mmol), Potassium ethanoate (17.6g, 0.18mol), 1,4-dioxane (560g), N
2protection, is warming up to backflow, and insulation reaction 8h stops heating, adds deionized water 100mL; slough organic solvent, add 500mL methylene dichloride, separatory, 100mL X2 deionized water wash organic phase; collect organic phase, desolventizing, gained crude product is through purification by silica gel column chromatography, and eluent is hexanaphthene: CH
2cl
2=8:1, obtains intermediate 2, gross weight 16.7g, yield 79.5%, MS (m/s): 467.2.
The preparation (compound 8) of embodiment 3 bis cyclohexanes carbazole
In 2L there-necked flask, add compound 4 (186.3g, 1.0mol), methylene dichloride (1400g), under room temperature, add NBS (178.0g in batches, 1.0mol), stirring at room temperature 4h, be warming up to backflow, insulation reaction 1h, be down to room temperature, 200mL X3 deionized water wash organic phase, collect organic phase, slough solvent, add sherwood oil (2.5L), be warming up to interior temperature >60 DEG C, organic phase is while hot fast by 200g silicagel column, collected post liquid, slough solvent, obtain compound 5, for colourless dope 281g, yield 106%, the thick product of gained no longer carries out purifying, be directly used in next step reaction.
Collect above compound 5 crude products in 5L there-necked flask, add THF (1500g), room temperature is dissolved, be cooled to Nei Wen-78 DEG C, drip the hexane solution (2.5mol/L of n-Butyl Lithium, 400mL, 1.0mmol), about 30min dropwises, insulation reaction 1.5h, by triisopropyl borate ester (197.4g, 1.05mol) be dissolved in 220g THF, slowly splash in 5L bottle, about 1.5h dropwises, insulation reaction 4.5h, after insulation finishes, during the low temperature of 0 DEG C of reaction flask immigration is bathed, naturally heat up, Nei Wen-5 DEG C, drip 10% dilute hydrochloric acid 750g, stir 1h, separatory, the water washing of 200mL X2 saturated common salt, collect organic phase, slough solvent, deionized water is solvent recrystallization, obtain compound 6, for off-white color solid 156.4g, yield 68%, the thick product of gained no longer carries out purifying, be directly used in next step reaction.
In 5L there-necked flask, add compound 6 (154g, 0.67mol), o-bromonitrobenzene (149.5g, 0.74mol), Pd (PPh
3)
4(8.4g, 0.0072mol), K
2cO
3(185g, 1.34mol), THF (1400g), deionized water (400g), be warming up to backflow, insulation reaction 24h, is down to room temperature, and organic solvent is sloughed in decompression, add methylene dichloride (1400g), separatory, 200mL X2 washes organic phase, collects organic phase, cross 180g silicagel column, slough solvent, obtain 240g oily liquids, taking dehydrated alcohol as solvent recrystallization, obtain compound 7, for pale solid 138g, yield 67.3%, MS (m/s): 307.2.
In 2L there-necked flask, add compound 7 (126g, 0.41mol), triphenylphosphine (325g, 1.24mol), orthodichlorobenzene (1500g), be warming up to backflow, insulation reaction 28h, cooling, underpressure distillation, desolvation, gained crude product, taking acetone: dehydrated alcohol=1:1 (W/W) as solvent recrystallization, obtain compound 8, gross weight 62.5g, yield 55.4%, MS (m/s): 275.2.
The preparation of embodiment 4 intermediates 3
The preparation of intermediate 3, in embodiment 1, the preparation method of intermediate 1 completes, and obtains intermediate 3, gross weight 37.5g, MS (m/s): 475.1.
The preparation of embodiment 5 intermediates 4
The preparation of intermediate 4, in embodiment 2, the preparation method of intermediate 2 completes, and obtains intermediate 4, gross weight 13.5g, yield 69%, MS (m/s): 475.2.
The preparation of embodiment 6 compounds 12
The preparation of compound 12, reference literature KR20110092262 completes, and reaction totally two steps, are respectively coupling and Guan Huan, obtain compound 12, gross weight 72.1g, two-step reaction total recovery 44.5%, MS (m/s): 269.1.
The preparation of embodiment 7 intermediates 5
The preparation of intermediate 5, in embodiment 1, the preparation method of intermediate 1 completes, and obtains intermediate 5, gross weight 42.7g, MS (m/s): 469.0.
The preparation of embodiment 8 intermediates 6
The preparation of intermediate 6, in embodiment 2, the preparation method of intermediate 2 completes, and obtains intermediate 6, gross weight 17.1g, yield 72.7%, MS (m/s): 469.2.
The preparation of embodiment 9 Compound C 002
In 250mL there-necked flask, add intermediate 1 (1.6g, 3.4mmol), phenylo boric acid (0.5g, 4.1mmol), Pd (PPh
3)
4(0.2g), THF (25mL), deionized water (12mL), salt of wormwood (1.2g, 8.8mmol), be warming up to backflow, insulation reaction 24h, cooling, decompression steams THF, adds methylene dichloride 50mL, separatory, 20mL deionized water wash organic phase, collect organic phase, desolventizing, gained crude product is crossed purification by silica gel column chromatography, eluent is sherwood oil: ethyl acetate=8:1, obtain 1.11g Compound C 002, use the chemical gas-phase deposition system purification that further distils, 235 DEG C of sublimation temperatures, obtain 0.91g target compound C002, yield 64.5%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
32h
19n, theoretical value 417.1517, test value 417.1524.Ultimate analysis (C
32h
19n), theoretical value C:92.06, H:4.59, N:3.35, measured value C:92.11, H:4.58, N:3.31.
The preparation of embodiment 10 Compound C 006
Taking intermediate 1 and 4-phenyl-1-naphthalene boronic acids as raw material, according to the preparation of method described in embodiment 9, yield 68.2%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
42h
25n, theoretical value 543.1987, test value 543.1985.Ultimate analysis (C
42h
25n), theoretical value C:92.79, H:4.64, N:2.58, measured value C:92.76, H:4.65, N:2.59.
The preparation of embodiment 11 Compound C 010
Taking intermediate 1 and 9-naphthyl-10-anthracene boric acid as raw material, according to the preparation of method described in embodiment 9, yield 59.7%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
50h
29n, theoretical value 643.2300, test value 643.2308.Ultimate analysis (C
50h
29n), theoretical value C:93.28, H:4.54, N:2.18, measured value C:93.29, H:4.52, N:2.18.
The preparation of embodiment 12 Compound C 018
With intermediate 1 and 9,9'-spiral shell, two fluorenes-2-boric acid for raw material, according to the preparation of method described in embodiment 9, yield 66.3%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
51h
29n, theoretical value 655.2300, test value 655.2304.Ultimate analysis (C
51h
29n), theoretical value C:93.41, H:4.46, N:2.14, measured value C:93.46, H:4.44, N:2.10.
The preparation of embodiment 13 Compound C 023
Taking intermediate 1 and triphenylene-2-boric acid as raw material, according to the preparation of method described in embodiment 9, yield 72.1%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
44h
25n, theoretical value 567.1987, test value 567.1986.Ultimate analysis (C
44h
25n), theoretical value C:93.09, H:4.44, N:2.47, measured value C:93.10, H:4.45, N:2.45.
The preparation of embodiment 14 Compound C 024
In 100mL there-necked flask, add compound intermediate 1 (1.8g, 3.8mmol), carbazole (1.9g, 11.4mmol), CuI (0.36g, 1.9mmol), phenanthroline (0.68g, 3.8mmol), salt of wormwood (2.2g, 15.9mmol), orthodichlorobenzene (60mL), be warming up to 160 DEG C of interior temperature, insulation reaction 12h, be down to room temperature, add toluene 50mL, 20mL X2 deionized water wash organic phase, separatory, collect organic phase, decompression desolventizing, gained crude product is crossed purification by silica gel column chromatography, eluent is sherwood oil: methylene dichloride=2:1, obtain 1.3g Compound C 024, use the chemical gas-phase deposition system purification that further distils, 300 DEG C of sublimation temperatures, obtain 1.1g target compound C024, yield 57.3%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
38h
22n
2, theoretical value 506.1783, test value 506.1788.Ultimate analysis (C
38h
22n
2), theoretical value C:90.09, H:4.38, N:5.53, measured value C:90.11, H:4.33, N:5.56.
The preparation of embodiment 15 Compound C 028
Taking intermediate 1 and N-phenyl carbazole-3-boric acid as raw material, according to the preparation of method described in embodiment 9, yield 69.7%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
44h
26n
2, theoretical value 582.2096, test value 582.2093.Ultimate analysis (C
44h
26n
2), theoretical value C:90.69, H:4.50, N:4.81, measured value C:90.72, H:4.52, N:4.79.
The preparation of embodiment 16 Compound C 040
Taking intermediate 3 and 9-naphthalene anthracene-10-boric acid as raw material, according to the preparation of method described in embodiment 9, yield 67.1%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
50h
37n, theoretical value 651.2926, test value 651.2928.Ultimate analysis (C
50h
37n), theoretical value C:92.13, H:5.72, N:2.15, measured value C:92.15, H:5.73, N:2.12.
The preparation of embodiment 17 Compound C 042
Taking the luxuriant and rich with fragrance boric acid of intermediate 3 and 9-as raw material, according to the preparation of method described in embodiment 9, yield 56.7%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
40h
31n, theoretical value 525.2456, test value 525.2458.Ultimate analysis (C
40h
31n), theoretical value C:91.39, H:5.94, N:2.66, measured value C:91.38, H:5.95, N:2.67.
The preparation of embodiment 18 Compound C 058
Taking intermediate 3 and N-phenyl-carbazole-3-boric acid as raw material, according to the preparation of method described in embodiment 9, yield 55.7%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
44h
34n
2, theoretical value 590.2722, test value 590.2724.Ultimate analysis (C
44h
34n
2), theoretical value C:89.46, H:5.80, N:4.74, measured value C:89.45, H:5.82, N:4.73.
The preparation of embodiment 19 Compound C 071
Taking the luxuriant and rich with fragrance boric acid of intermediate 5 and 9-as raw material, according to the preparation of method described in embodiment 9, yield 61.5%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
38h
21n
3, theoretical value 519.1735, test value 519.1733.Ultimate analysis (C
38h
21n
3), theoretical value C:87.84, H:4.07, N:8.09, measured value C:87.84, H:4.08, N:8.08.
The preparation of embodiment 20 Compound C 081
Taking intermediate 5 and triphenylene-2-boric acid as raw material, according to the preparation of method described in embodiment 9, yield 49.8%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
42h
23n
3, theoretical value 569.1892, test value 569.1894.Ultimate analysis (C
42h
23n
3), theoretical value C:88.55, H:4.07, N:7.38, measured value C:88.56, H:4.09, N:7.35.
The preparation of embodiment 21 Compound C 082
Taking intermediate 5 and carbazole as raw material, according to the preparation of method described in embodiment 14, yield 49.8%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
36h
20n
4, theoretical value 508.1688, test value 508.1689.Ultimate analysis (C
36h
20n
4), theoretical value C:85.02, H:3.96, N:11.02, measured value C:85.04, H:3.98, N:10.98.
The preparation of embodiment 22 Compound C 083
With intermediate 5 and 3,6-dimethyl-9H-carbazole for raw material, according to the preparation of method described in embodiment 14, yield 69.2%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
38h
24n
4, theoretical value 536.2001, test value 536.2003.Ultimate analysis (C
38h
24n
4), theoretical value C:85.05, H:4.51, N:10.44, measured value C:85.04, H:4.50, N:10.46.
The preparation of embodiment 23 Compound C 093
In 250mL there-necked flask, add compound intermediate 2 (1.6g, 3.4mmol), 2-(3-Xiu – phenyl)-[1,8] naphthyridines (0.97g, 3.4mmol), Pd (PPh
3)
4(0.30g, 0.26mmol), THF (35mL), deionized water (18mL), salt of wormwood (2.3g, 16.6mmol), be warming up to backflow, insulation reaction 36h, cooling, decompression steams THF, add methylene dichloride 150mL, separatory, 30mL deionized water wash, collect organic phase, desolventizing, obtain thick product 1.72g, gained crude product is crossed purification by silica gel column chromatography, eluent is sherwood oil: ethyl acetate=2:1, obtain 1.31g Compound C 093, use the chemical gas-phase deposition system purification that further distils, 345 DEG C of sublimation temperatures, obtain 1.2g target compound C093, yield 64.8%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
40h
23n
3, theoretical value 545.1892, test value 545.1986.Ultimate analysis (C
40h
23n
3), theoretical value C:88.05, H:4.25, N:7.70, measured value C:88.08, H:4.26, N:7.66.
The preparation of embodiment 24 Compound C 098
With intermediate 2 and 3,5-bis-(4-pyridine) bromobenzene for raw material, according to the preparation of method described in embodiment 23, yield 55.7%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
42h
25n
3, theoretical value 571.2048, test value 571.2046.Ultimate analysis (C
42h
25n
3), theoretical value C:88.24, H:4.41, N:7.35, measured value C:88.26, H:4.40, N:7.34.
The preparation of embodiment 25 Compound C 099
Taking intermediate 2 and 3-(4-pyridine)-5-(3-pyridine) bromobenzene as raw material, according to the preparation of method described in embodiment 23, yield 57.6%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
42h
25n
3, theoretical value 571.2048, test value 571.2049.Ultimate analysis (C
42h
25n
3), theoretical value C:88.24, H:4.41, N:7.35, measured value C:88.25, H:4.42, N:7.33.
The preparation of embodiment 26 Compound C 105
Taking intermediate 2 and 4-biphenyl-6-(the bromo-phenyl of 4-)-2-phenyl-pyrimidine as raw material, according to the preparation of method described in embodiment 23, yield 65.5%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
54h
33n
3, theoretical value 723.2674, test value 723.2677.Ultimate analysis (C
54h
33n
3), theoretical value C:89.60, H:4.60, N:5.81, measured value C:89.61, H:4.59, N:5.80.
The preparation of embodiment 27 Compound C 110
Taking intermediate 2 and 2-(the bromo-phenyl of 4-)-1-phenyl-1H-benzoglyoxaline as raw material, according to the preparation of method described in embodiment 23, yield 59.8%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
45h
27n
3, theoretical value 609.2205, test value 609.2208.Ultimate analysis (C
45h
27n
3), theoretical value C:88.64, H:4.46, N:6.89, measured value C:88.66, H:4.46, N:6.88.
The preparation of embodiment 28 Compound C 115
For raw material, prepare yield 71.5% with intermediate 4 and 2-bromo-[1,8] naphthyridines according to method described in embodiment 23.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
34h
27n
3, theoretical value 477.2205, test value 477.2208.Ultimate analysis (C
34h
27n
3), theoretical value C:85.50, H:5.70, N:8.80, measured value C:85.51, H:5.72, N:8.77.
The preparation of embodiment 29 Compound C 132
With intermediate 4 and 2-(the bromo-phenyl of 3-)-4,6-phenylbenzene-[1,3,5] triazine is raw material, according to the preparation of method described in embodiment 23, yield 69.8%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
47h
36n
4, theoretical value 656.2940, test value 656.2941.Ultimate analysis (C
47h
36n
4), theoretical value C:85.95, H:5.52, N:8.53, measured value C:85.96, H:5.54, N:8.50.
The preparation of embodiment 30 Compound C 145
Taking intermediate 6 and 3-(4-pyridine)-5-(3-pyridine) bromobenzene as raw material, according to the preparation of method described in embodiment 23, yield 57.2%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
40h
23n
5, theoretical value 573.1953, test value 573.1952.Ultimate analysis (C
40h
23n
5), theoretical value C:83.75, H:4.04, N:12.21, measured value C:83.77, H:4.03, N:12.20.
The preparation of embodiment 31 Compound C 151
Taking intermediate 6 and 4-biphenyl-6-(the bromo-phenyl of 4-)-2-phenyl-pyrimidine as raw material, according to the preparation of method described in embodiment 23, yield 73.2%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
52h
31n
5, theoretical value 725.2579, test value 725.2576.Ultimate analysis (C
52h
31n
5), theoretical value C:86.05, H:4.30, N:9.65, measured value C:86.06, H:4.31, N:9.63.
The preparation of embodiment 32 Compound C 153
With intermediate 6 and 2-(the bromo-phenyl of 4-)-4,6-phenylbenzene-[1,3,5] triazine is raw material, according to the preparation of method described in embodiment 23, yield 59.3%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
45h
26n
6, theoretical value 650.2219, test value 650.2220.Ultimate analysis (C
45h
26n
6), theoretical value C:83.06, H:4.03, N:12.91, measured value C:83.08, H:4.01, N:12.91.
The preparation of embodiment 33 Compound C 156
Taking intermediate 6 and 2-(the bromo-phenyl of 4-)-1-phenyl-1H-benzoglyoxaline as raw material, according to the preparation of method described in embodiment 23, yield 69.7%.
High resolution mass spectrum, ESI source, positive ion mode, molecular formula C
43h
25n
5, theoretical value 611.2110, test value 611.2111.Ultimate analysis (C
43h
25n
5), theoretical value C:84.43, H:4.12, N:11.45, measured value C:84.44, H:4.16, N:11.40.
Organic electroluminescence device embodiment:
The present invention chooses Compound C 006, Compound C 010, Compound C 023, Compound C 040, Compound C 058 and Compound C 071 are made first group of organic electroluminescence device, and device architecture is as shown in Figure 1, be to be understood that, device implementation process and result, just in order to explain better the present invention, not limitation of the present invention.
Embodiment 34 application of Compound C 006 in organic electroluminescence device
The present embodiment is prepared with organic electroluminescence devices one by the following method:
A) clean ITO (tin indium oxide) glass: use respectively deionized water, acetone, ethanol ultrasonic cleaning ito glass each 30 minutes, then in plasma clean device, process 5 minutes;
B) on anode ito glass, vacuum evaporation hole transmission layer NPB, thickness is 50nm;
C) on hole transmission layer NPB, vacuum evaporation luminescent layer Compound C 006, thickness is 30nm;
D) on luminescent layer, vacuum evaporation electron transfer layer TPBI, thickness is 30nm;
E) on electron transfer layer TPBI, vacuum evaporation electron injecting layer LiF, thickness is 1nm;
F) on electron injecting layer, vacuum evaporation negative electrode Al, thickness is 100nm.
The structure of device one is ITO/NPB (50nm)/Compound C 006 (30nm)/TPBI (30nm)/LiF (1nm)/Al (100nm), in vacuum evaporation process, and pressure <1.0X10
-3pa, device one open bright voltage, maximum current efficiency, the photooptical datas such as purity of color see below civilian table 1 (in embodiment 39).
Embodiment 35 application of Compound C 010 in organic electroluminescence device
Replace Compound C 006 as luminescent layer using Compound C 010, according to method described in embodiment 34, be manufactured with organic electroluminescence devices two, the structure of device two is ITO/NPB (50nm)/Compound C 010 (30nm)/TPBI (30nm)/LiF (1nm)/Al (100nm), device two open bright voltage, maximum current efficiency, the photooptical datas such as purity of color see below civilian table 1.
Embodiment 36 application of Compound C 023 in organic electroluminescence device
Using Compound C 023 as luminescent layer, according to method described in embodiment 34, be manufactured with organic electroluminescence devices three, the structure of device three is ITO/NPB (50nm)/Compound C 023 (30nm)/TPBI (30nm)/LiF (1nm)/Al (100nm), device three open bright voltage, maximum current efficiency, the photooptical datas such as purity of color, list in hereinafter in table 1.
Embodiment 37 application of Compound C 040 in organic electroluminescence device
Using Compound C 040 as luminescent layer, according to method described in embodiment 34, be manufactured with organic electroluminescence devices four, the structure of device four is ITO/NPB (50nm)/Compound C 040 (30nm)/TPBI (30nm)/LiF (1nm)/Al (100nm), device four open bright voltage, maximum current efficiency, the photooptical datas such as purity of color see below civilian table 1.
Embodiment 38 application of Compound C 058 in organic electroluminescence device
Using Compound C 058 as luminescent layer, according to method described in embodiment 34, be manufactured with organic electroluminescence devices five, the structure of device five is ITO/NPB (50nm)/Compound C 058 (30nm)/TPBI (30nm)/LiF (1nm)/Al (100nm), device five open bright voltage, maximum current efficiency, the photooptical datas such as purity of color see below civilian table 1.
Embodiment 39 application of Compound C 071 in organic electroluminescence device
Using Compound C 071 as luminescent layer, according to method described in embodiment 34, be manufactured with organic electroluminescence devices six, the structure of device six is ITO/NPB (50nm)/Compound C 071 (30nm)/TPBI (30nm)/LiF (1nm)/Al (100nm), device six open bright voltage, maximum current efficiency, the photooptical datas such as purity of color are in table 1.
Table 1 device one is to device six photooptical data tables
The present invention chooses Compound C 099, Compound C 105, and Compound C 110 and Compound C 115 are made second group of organic electroluminescence device, device architecture as shown in Figure 2, should be appreciated that device implementation process and result,, in order to explain better the present invention, be not just limitation of the present invention.
Embodiment 40 application of Compound C 099 in organic electroluminescence device
The present embodiment is prepared with organic electroluminescence devices seven by the following method:
A) clean ITO (tin indium oxide) glass: use respectively deionized water, acetone, ethanol ultrasonic cleaning ito glass each 30 minutes, then in plasma clean device, process 5 minutes;
B) on anode ito glass, vacuum evaporation hole transmission layer NPB, thickness is 50nm;
C) on hole transmission layer NPB, vacuum evaporation is simultaneously as the Compound C 099 of luminescent layer and electron transfer layer, and thickness is 60nm;
D) on Compound C 099, vacuum evaporation electron injecting layer LiF, thickness is 1nm;
E) on electron injecting layer, vacuum evaporation negative electrode Al, thickness is 100nm.
The structure of device seven is ITO/NPB (50nm)/Compound C 099 (60nm)/LiF (1nm)/Al (100nm), in vacuum evaporation process, and pressure <1.0X10
-3pa, device seven open bright voltage, maximum current efficiency, the photooptical datas such as purity of color see below civilian table 2.
Embodiment 41 application of Compound C 105 in organic electroluminescence device
Replace Compound C 099 as luminescent layer and electron transfer layer using Compound C 105, according to method described in embodiment 40, be manufactured with organic electroluminescence devices eight, the structure of device eight is ITO/NPB (50nm)/Compound C 105 (60nm)/LiF (1nm)/Al (100nm), device eight open bright voltage, maximum current efficiency, the photooptical datas such as purity of color see below civilian table 2.
Embodiment 42 application of Compound C 110 in organic electroluminescence device
Using Compound C 110 as luminescent layer with electron transfer layer, according to method described in embodiment 40, be manufactured with organic electroluminescence devices nine, the structure of device nine is ITO/NPB (50nm)/Compound C 110 (60nm)/LiF (1nm)/Al (100nm), device nine open bright voltage, maximum current efficiency, the photooptical datas such as purity of color are in table 2.
Embodiment 43 application of Compound C 115 in organic electroluminescence device
Using Compound C 115 as luminescent layer with electron transfer layer, according to method described in embodiment 40, be manufactured with organic electroluminescence devices ten, the structure of device ten is ITO/NPB (50nm)/Compound C 115 (60nm)/LiF (1nm)/Al (100nm), device ten open bright voltage, maximum current efficiency, the photooptical datas such as purity of color are in table 2.
Table 2 device seven is to device ten photooptical data tables
The present invention chooses Compound C 145, and Compound C 151 and Compound C 156 are made the 3rd group of organic electroluminescence device, and device architecture as shown in Figure 1, be to be understood that, device implementation process and result, just in order to explain better the present invention, not limitation of the present invention.
Embodiment 44 application of Compound C 145 in organic electroluminescence device
The present embodiment is prepared with organic electroluminescence devices 11 by the following method:
A) clean ITO (tin indium oxide) glass: use respectively deionized water, acetone, ethanol ultrasonic cleaning ito glass each 30 minutes, then in plasma clean device, process 5 minutes;
B) on anode ito glass, vacuum evaporation hole transmission layer NPB, thickness is 50nm;
C) on hole transmission layer NPB, vacuum evaporation luminescent layer AIq
3, thickness is 30nm;
D) at luminescent layer AIq
3on, vacuum evaporation electron transfer layer Compound C 145, thickness is 30nm;
E) on electron transfer layer, vacuum evaporation electron injecting layer LiF, thickness is 1nm;
F) on electron injecting layer, vacuum evaporation negative electrode Al, thickness is 100nm.
The structure of device 11 is ITO/NPB (50nm)/AIq
3(30nm)/Compound C 145 (30nm)/LiF (1nm)/Al (100nm), in vacuum evaporation process, pressure <1.0X10
-3pa, device 11 open bright voltage, maximum current efficiency, the photooptical datas such as purity of color, list in hereinafter in table 3.
Embodiment 45 application of Compound C 151 in organic electroluminescence device
Replace Compound C 145 as electron transfer layer using Compound C 151, according to method described in embodiment 44, be manufactured with organic electroluminescence devices 12, the structure of device 12 is ITO/NPB (50nm)/AIq
3(30nm)/Compound C 151 (30nm)/LiF (1nm)/Al (100nm), device 12 open bright voltage, maximum current efficiency, the photooptical datas such as purity of color are listed in table 3.
Embodiment 46 application of Compound C 156 in organic electroluminescence device
Using Compound C 156 as electron transfer layer, according to method described in embodiment 46, be manufactured with organic electroluminescence devices 13, the structure of device 13 is ITO/NPB (50nm)/AIq
3(30nm)/Compound C 156 (30nm)/LiF (1nm)/Al (100nm), device 13 open bright voltage, maximum current efficiency, the photooptical datas such as purity of color, are listed in the table below in 3.
Table 3 device 11 is to device 13 photooptical data tables
Claims (6)
1. an organic electroluminescent LED material, is characterized in that, comprises any one in structure shown in following formula I, formula II, formula III:
2. a kind of organic electroluminescent LED material according to claim 1, is characterized in that, described R1, and R2, R4～R7 is independently selected from hydrogen atom, cyano group, the alkyl of C1～C40, alkoxyl group, aromatic base or the substituting group containing element silicon.
3. a kind of organic electroluminescent LED material according to claim 2, is characterized in that, described R1, and R2, R4～R7 is identical.
4. a kind of organic electroluminescent LED material according to claim 2, is characterized in that, described R1, and R2, R4～R7 is not identical.
5. a kind of organic electroluminescent LED material according to claim 1, is characterized in that, R3 is selected from hydrogen atom, contain substituting group or containing substituent aromatic nucleus or aromatic heterocycle.
6. an application for organic electroluminescent LED material, is characterized in that, in the organic electroluminescent LED (OLED) of preparation, has a functional layer at least, contains organic electroluminescent LED material described in claim 1 to 4 any one.
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