CN106588934A - Carbazole derivative, preparation method, and application thereof - Google Patents
Carbazole derivative, preparation method, and application thereof Download PDFInfo
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- CN106588934A CN106588934A CN201611057161.XA CN201611057161A CN106588934A CN 106588934 A CN106588934 A CN 106588934A CN 201611057161 A CN201611057161 A CN 201611057161A CN 106588934 A CN106588934 A CN 106588934A
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- substituted
- unsubstituted
- analog derivative
- carbazole analog
- aryl
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- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title claims abstract 19
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 238000005401 electroluminescence Methods 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 239000005416 organic matter Substances 0.000 claims description 7
- 230000005540 biological transmission Effects 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 239000000463 material Substances 0.000 abstract description 11
- 239000002994 raw material Substances 0.000 abstract description 4
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 230000005525 hole transport Effects 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 230000006872 improvement Effects 0.000 abstract description 2
- 230000001788 irregular Effects 0.000 abstract description 2
- 229920001621 AMOLED Polymers 0.000 abstract 1
- 230000009477 glass transition Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 55
- 238000004364 calculation method Methods 0.000 description 35
- 239000000470 constituent Substances 0.000 description 35
- 238000001819 mass spectrum Methods 0.000 description 35
- 238000005259 measurement Methods 0.000 description 35
- 239000010410 layer Substances 0.000 description 26
- 150000001716 carbazoles Chemical class 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 22
- 238000000034 method Methods 0.000 description 11
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 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 8
- 239000004305 biphenyl Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 229910001868 water Inorganic materials 0.000 description 5
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 4
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical class C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- -1 xenyl Chemical group 0.000 description 3
- QFUYDAGNUJWBSM-UHFFFAOYSA-N 1-iodo-2-phenylbenzene Chemical group IC1=CC=CC=C1C1=CC=CC=C1 QFUYDAGNUJWBSM-UHFFFAOYSA-N 0.000 description 2
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 2
- 102100024233 High affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7A Human genes 0.000 description 2
- 101001117267 Homo sapiens High affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7A Proteins 0.000 description 2
- 208000036626 Mental retardation Diseases 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 1
- UTDMSJMYYBXEPR-UHFFFAOYSA-N 1-bromo-2-iodoethene Chemical class BrC=CI UTDMSJMYYBXEPR-UHFFFAOYSA-N 0.000 description 1
- MFNHMOXVXWPIQL-UHFFFAOYSA-N 1-iodo-9h-fluorene Chemical class C12=CC=CC=C2CC2=C1C=CC=C2I MFNHMOXVXWPIQL-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- UWVQOVPKNIPJCA-UHFFFAOYSA-N 2-(2-methylphenyl)-1h-phenanthro[9,10-d]imidazole Chemical compound CC1=CC=CC=C1C1=NC(C2=CC=CC=C2C2=CC=CC=C22)=C2N1 UWVQOVPKNIPJCA-UHFFFAOYSA-N 0.000 description 1
- GMNOXGNZDZVBHX-UHFFFAOYSA-N 2-[[5-(4-bromophenyl)-1-methylpyrrol-2-yl]methylidene]propanedinitrile Chemical compound CN1C(C=C(C#N)C#N)=CC=C1C1=CC=C(Br)C=C1 GMNOXGNZDZVBHX-UHFFFAOYSA-N 0.000 description 1
- 0 CC(c(cccc1)c1N*)=*C=CC(*[n]1c2nc(cccc3)c3[n]2c2ccccc12)=C Chemical compound CC(c(cccc1)c1N*)=*C=CC(*[n]1c2nc(cccc3)c3[n]2c2ccccc12)=C 0.000 description 1
- GMEJYXSQKMXRBF-UHFFFAOYSA-N CCC(C)C1=CCSC=C1 Chemical compound CCC(C)C1=CCSC=C1 GMEJYXSQKMXRBF-UHFFFAOYSA-N 0.000 description 1
- 208000035126 Facies Diseases 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- KLACMEYLRXQSMN-UHFFFAOYSA-N c(cc1)cc([nH]2)c1[n]1c2nc2ccccc12 Chemical compound c(cc1)cc([nH]2)c1[n]1c2nc2ccccc12 KLACMEYLRXQSMN-UHFFFAOYSA-N 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- SXTLQDJHRPXDSB-UHFFFAOYSA-N copper;dinitrate;trihydrate Chemical compound O.O.O.[Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O SXTLQDJHRPXDSB-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical class Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000000007 visual effect Effects 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
- C07D487/04—Ortho-condensed systems
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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
- 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
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- 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
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- 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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- 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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- 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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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a carbazole derivative, a preparation method, and an application thereof, and relates to the technical field of organic photoelectric materials. Through introduction of a condensed-ring rigid and dense structure, the carbazole derivative has high molecular weight, which is beneficial to improvement of glass transition temperature. Meanwhile, because the substituent groups on the compound are non-planar, the whole molecule, stereoscopically, has a twisted structure in certain degree, wherein the spatial stereoscopic structure of the molecule is irregular, which is beneficial to formation of an amorphous film. The carbazole derivative can be used for producing an OLED, and especially, can be used as a hole transport material in the OLED. The carbazole derivative effectively improves luminous efficiency of the OLED and has long service life, and has a prospect of application in AMOLED industry. The invention also provides a preparation method of the carbazole derivative, which is simple and employs easy-to-obtain raw materials.
Description
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to a kind of carbazole analog derivative and preparation method thereof and
Using.
Background technology
With the progress of information industry, traditional display can not meet the requirement of people, such as：Cathode ray tube
(cathode ray tube, CRT) display volume is big, driving voltage is high；Liquid crystal display (liquid crystal
Display, LCD) brightness is low, narrow viewing angle, operating temperature range are little；Plasma display (plasma display panel,
PDP) involve great expense, resolution is not high, power consumption is big.
Organic electroluminescent LED (organic light-emitting diodes, OLEDs) is used as a kind of brand-new
Display Technique possesses the unmatched advantage of existing Display Technique in each performance, such as have it is all solid state, from main light emission, brightness
Height, high-resolution, visual angle width (more than 170 degree), fast response time, thickness of thin, small volume, it is lightweight, can using flexible base board,
Low-voltage direct-current drives (3-10V), low in energy consumption, operating temperature range width etc. so that its application market is quite varied, such as illuminates
System, communication system, car-mounted display, portable electric appts, fine definition show even military field.
All in all, the direction of following OLED be develop high efficiency, high brightness, the long-life, low cost white light parts and
Full color display device, but the technological industrialization process still faces many key issues.Therefore, design and a kind of chemical combination of searching
Thing, occurs, in being OLED material research work to overcome the shortcomings of it as OLED new materials in actual application
Emphasis and Development Trend from now on.
The content of the invention
It is an object of the invention to provide a kind of carbazole analog derivative and its preparation method and application, it is organic that the present invention is provided
Simply, the organic luminescent device by made by the compound shows for compound thermal stability height, good film-forming property and preparation method
Luminous efficiency is high, and the advantage of life-span length is the luminous organic material of function admirable.
Present invention firstly provides a kind of carbazole analog derivative, structural formula is：
Wherein, R1Unsaturated alkyl, the virtue of substituted or unsubstituted C6-C60 selected from substituted or unsubstituted C2-C4
One kind in base, the condensed ring of substituted or unsubstituted C10～C60, the condensed hetero ring of substituted or unsubstituted C8～C60；R2It is selected from
One kind in the aryl of substituted or unsubstituted C6-C60, the condensed ring of substituted or unsubstituted C10～C60.
Preferably, the R1Unsaturated alkyl, substituted or unsubstituted C6-C30 selected from substituted or unsubstituted C2-C4
Aryl, the condensed ring of substituted or unsubstituted C10～C30, the condensed hetero ring of substituted or unsubstituted C8～C30 in one kind；R2
One kind in aryl, the condensed ring of substituted or unsubstituted C10～C30 selected from substituted or unsubstituted C6-C30.
Preferably, the R1Unsaturated alkyl, substituted or unsubstituted C6-C18 selected from substituted or unsubstituted C2-C4
Aryl, the condensed ring of substituted or unsubstituted C10～C24 in one kind；R2Aryl selected from substituted or unsubstituted C6-C12,
One kind in the condensed ring of substituted or unsubstituted C10～C14.
Preferably, the R1Selected from vinyl, phenyl, naphthyl, anthryl, xenyl, terphenyl, fluorenyl, the fluorenyl of spiral shell two
Or carbazyl；R2Selected from phenyl, naphthyl or xenyl.
Preferably, any one of the carbazole analog derivative in structure shown in following TM1～TM24：
The present invention also provides a kind of preparation method of carbazole analog derivative, and syntheti c route is as follows：
Wherein, R1Unsaturated alkyl, the virtue of substituted or unsubstituted C6-C60 selected from substituted or unsubstituted C2-C4
One kind in base, the condensed ring of substituted or unsubstituted C10～C60, the condensed hetero ring of substituted or unsubstituted C8～C60；R2It is selected from
One kind in the aryl of substituted or unsubstituted C6-C60, the condensed ring of substituted or unsubstituted C10～C60.
The present invention also provides application of the carbazole analog derivative in organic electroluminescence device.
Preferably, the organic electroluminescence device includes anode, negative electrode and organic matter layer, contains in the organic matter layer
Carbazole analog derivative described in any one.
Preferably, the carbazole analog derivative is used to prepare the hole transmission layer of organic electroluminescence device.
Beneficial effects of the present invention:
Present invention firstly provides a kind of carbazole analog derivative, the carbazole analog derivative has structure shown in formula I, by introducing
Condensed ring class rigidity, close packed structure so that the carbazole analog derivative obtained by the present invention has higher molecular weight, is conducive to glass
Change the raising of temperature, simultaneously as each substituent group on the compound is in on-plane surface state so that whole molecule is vertical in space
Distortion to a certain extent is formed on body, the stereoeffect of molecule is irregular, advantageously forms unformed film.Institute of the present invention
The carbazole analog derivative for obtaining can be used to prepare organic electroluminescence device, especially as the sky in organic electroluminescence device
Hole transport materials, show luminous efficiency height, the advantage of life-span length, better than existing conventional OLED.The present invention also provides one
The preparation method of carbazole analog derivative is planted, the preparation method is simple, raw material is easy to get, and disclosure satisfy that the needs of industrialization development.This
Invention carbazole analog derivative has good application effect in OLED luminescent devices, with good industrialization prospect.
Specific embodiment
For a further understanding of the present invention, the preferred embodiment of the invention is described with reference to embodiment, but
It should be appreciated that these descriptions are simply to further illustrate the features and advantages of the present invention, rather than to the claims in the present invention
Limit.
Present invention firstly provides a kind of carbazole analog derivative, structural formula is：
Wherein, R1Unsaturated alkyl, the virtue of substituted or unsubstituted C6-C60 selected from substituted or unsubstituted C2-C4
One kind in base, the condensed ring of substituted or unsubstituted C10～C60, the condensed hetero ring of substituted or unsubstituted C8～C60；R2It is selected from
One kind in the aryl of substituted or unsubstituted C6-C60, the condensed ring of substituted or unsubstituted C10～C60.
Preferably R1Unsaturated alkyl, the virtue of substituted or unsubstituted C6-C30 selected from substituted or unsubstituted C2-C4
One kind in base, the condensed ring of substituted or unsubstituted C10～C30, the condensed hetero ring of substituted or unsubstituted C8～C30；R2It is selected from
One kind in the aryl of substituted or unsubstituted C6-C30, the condensed ring of substituted or unsubstituted C10～C30.
According to the present invention, in described substituted aryl, the condensed ring of replacement, the condensed hetero ring of replacement, the choosing of substituent group independence
From alkyl, alkoxyl, amino, halogen, cyano group, nitro, hydroxyl or sulfydryl.
Further preferably R1Unsaturated alkyl, the virtue of substituted or unsubstituted C6-C18 selected from substituted or unsubstituted C2-C4
One kind in base, the condensed ring of substituted or unsubstituted C10～C24；R2Aryl, replacement selected from substituted or unsubstituted C6-C12
Or the one kind in the condensed ring of unsubstituted C10～C14.
Most preferably R1Selected from vinyl, phenyl, naphthyl, anthryl, xenyl, terphenyl, fluorenyl, the fluorenyl of spiral shell two or carbazole
Base；R2Selected from phenyl, naphthyl or xenyl.
Specifically, the carbazole analog derivative is preferably selected from any one in structure shown in following TM1～TM24：
The present invention also provides a kind of preparation method of carbazole analog derivative, and syntheti c route is as follows：
Wherein, R1Unsaturated alkyl, the virtue of substituted or unsubstituted C6-C60 selected from substituted or unsubstituted C2-C4
One kind in base, the condensed ring of substituted or unsubstituted C10～C60, the condensed hetero ring of substituted or unsubstituted C8～C60；R2It is selected from
One kind in the aryl of substituted or unsubstituted C6-C60, the condensed ring of substituted or unsubstituted C10～C60.
According to the present invention, the compound shown in intermediate A is prepared according to method as follows：
Carbazole obtains intermediate A via nitration reaction and reduction reaction.
According to the present invention, the compound shown in intermediate B is prepared according to method as follows：
Under nitrogen protection, palladium and tri-butyl phosphine are catalyst, in the case that sodium tert-butoxide is alkali, benzimidazole
And<1,2-A>Benzimidazole obtains intermediate B with halides via Buchwald-Hartwig coupling reactions.
According to the present invention, the compound shown in target product is prepared according to method as follows：
Under nitrogen protection, palladium and tri-butyl phosphine are catalyst, in the case that sodium tert-butoxide is alkali, intermediate B
Target product is obtained with intermediate A via Buchwald-Hartwig coupling reactions.
According to the present invention, the compound and synthesis target product shown in synthetic intermediate B is to pass through under nitrogen protection
Coupling reaction is obtained, and the present invention does not have special restriction to the coupling reaction, using idol well-known to those skilled in the art
Connection reaction, the preparation method is simple, and raw material is easy to get.
The present invention also provides application of the carbazole analog derivative in organic electroluminescence device, the carbazoles of the present invention
Derivant can be applied as hole mobile material in terms of organic electroluminescence device, the organic electroluminescence device
Including anode, negative electrode and organic matter layer, organic matter layer comprising hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer,
At least one of which in hole blocking layer, electron transfer layer, electron injecting layer；At least one of which in the organic matter layer contains above-mentioned
Described carbazole analog derivative.The carbazole analog derivative specifically can be used as the hole transport for preparing organic electroluminescence device
Layer.Using device architecture be preferably specially：BH1 and BD1 is used as luminescent layer material, and Alq3 is used as electron-transporting material, described
Carbazole analog derivative be used as hole transmission layer material, to the organic luminescent device for manufacturing construction same as below：ITO/ institutes
Carbazole analog derivative/the BH1 for stating:BD1/Alq3/LiF/Al.The organic electroluminescence device can be used for flat faced display, shine
The applications such as Mingguang City source, direction board, signal lighties.
The present invention has no particular limits to the raw material employed in following examples, can be for commercially available prod or using this
Preparation method known to art personnel is prepared.
Embodiment A：
(A1)：The preparation of intermediate A 1
Gerhardite (9.9g, 41mmol), acetic acid (75mL), acetic anhydride (125mL) are placed in single port bottle (1L),
Stirring adds N- phenyl carbazoles (20g, 8.22mmol) after 10 minutes, heats 30 minutes at 30 DEG C.Then, add in system
Water (500mL) is filtered and rinses filter cake with water to obtain yellow solid.Afterwards, stirred using ethyl acetate and rinsed, after filtration
Obtain light yellow product.
By above-mentioned light yellow solid (15.5g, 53.8mmol), two hydrous tin chlorides (60.7g, 269mmol), ethyl acetate
(270mL) it is placed in 1L single port bottles with ethanol (270mL).It is stirred at reflux at 90 DEG C 10 hours, after being cooled to room temperature, is poured into
In the sodium hydroxide saturated aqueous solution of 2M, collected organic layer after ethyl acetate extraction afterwards.It is dried after concentration and obtains intermediate A 1
(yield is 74%).
Mass spectrum m/z：258.16 (value of calculation：258.12).Theoretical elemental content (%) C18H14N2：C,83.69；H,5.46；
N, 10.84 actual measurements constituent content (%)：C,83.67；H,5.47；N,10.85.The above results confirm to obtain product for target product
Product.
(A2)：The preparation of intermediate A 2
N- phenyl carbazoles in embodiment A1 are replaced with into equimolar 9- (1- naphthyls) carbazole, other steps with enforcement
A1 is identical for example, obtains intermediate A 2.Mass spectrum m/z：308.16 (value of calculation：308.13).Theoretical elemental content (%) C22H16N2：C,
85.69；H,5.23；N, 9.08 actual measurements constituent content (%)：C,85.69；H,5.24；N,9.07.The above results confirm to be produced
Thing is target product.
(A3)：The preparation of intermediate A 3
N- phenyl carbazoles in embodiment A1 are replaced with into equimolar 9- xenyls carbazole, other steps are and embodiment
A1 is identical, obtains intermediate A 3.Mass spectrum m/z：334.12 (value of calculation：334.15).Theoretical elemental content (%) C24H18N2：C,
86.20；H,5.43；N, 8.38 actual measurements constituent content (%)：C,86.21；H,5.42；N,8.37.The above results confirm to be produced
Thing is target product.
Embodiment B：
(B1) preparation of intermediate B 1
By tri-butyl phosphine (toluene solution of the 1.0M of 3mL, 7.32mmol), palladium (0.4g, 1.83mmol) and uncle
Sodium butoxide (22.8g, 238mmol) adds to benzimidazole simultaneously<1,2-A>Benzimidazole (37.7g, 183mmol) and 4- it is bromo- 4 '-
Iodo- 1, solution of the 1 '-biphenyl (65.5g, 183mmol) in degassed toluene (500mL), and the mixture is added under reflux
Heat 2 hours.The reactant mixture is cooled to into room temperature, is filtered with dilution with toluene and via kieselguhr.The filtrate water is dilute
Release, and use methylbenzene extraction, and merge organic faciess, it is evaporated under vacuo.The residue was carried out via silica gel
Filter, is recrystallized to give intermediate B 1 (67.0g, theoretical value 80%).
Mass spectrum m/z：437.06 (value of calculation：437.05).Theoretical elemental content (%) C25H16BrN3：C,68.50；H,
3.68；Br,18.23；N, 9.59 actual measurements constituent content (%)：C,68.52；H,3.69；Br,18.22；N,9.58.The above results
Confirm that it is target product to obtain product.
(B2) preparation of intermediate B 2
By the 4- bromo- 4 '-iodo- 1 in embodiment B1,1 '-biphenyl replace with it is equimolar to bromo-iodobenzene, other steps with
Embodiment B1 is identical, obtains intermediate B 2.Mass spectrum m/z：361.03 (value of calculation：361.02).Theoretical elemental content (%)
C19H12BrN3：C,63.00；H,3.34；Br,22.06；N, 11.60 actual measurements constituent content (%)：C,63.02；H,3.31；Br,
22.04；N,11.63.The above results confirm that it is target product to obtain product.
(B3) preparation of intermediate B 3
By the 4- bromo- 4 '-iodo- 1 in embodiment B1,1 '-biphenyl replaces with the bromo- 10- iodine anthracenes of equimolar 9-, other steps
It is identical with embodiment B1, obtain intermediate B 3.Mass spectrum m/z：461.03 (value of calculation：461.05).Theoretical elemental content (%)
C27H16BrN3：C,70.14；H,3.49；Br,17.28；N, 9.09 actual measurements constituent content (%)：C,70.15；H,3.47；Br,
17.29；N,9.09.The above results confirm that it is target product to obtain product.
(B4) preparation of intermediate B 4
By the 4- bromo- 4 '-iodo- 1 in embodiment B1,1 '-biphenyl replaces with the bromo- 5- iodine naphthalenes of equimolar 1-, other steps
It is identical with embodiment B1, obtain intermediate B 4.Mass spectrum m/z：411.05 (value of calculation：411.04).Theoretical elemental content (%)
C23H14BrN3：C,70.14；H,3.42；Br,19.38；N, 10.19 actual measurements constituent content (%)：C,70.15；H,3.42；Br,
19.37；N,10.18.The above results confirm that it is target product to obtain product.
(B5) preparation of intermediate B 5
Bromo- 4 '-the iodo- 1,1 '-biphenyl of 4- in embodiment B1 is replaced with into the iodo- 9,9- dimethyl of the bromo- 7- of equimolar 2-
Fluorenes, other steps are identical with embodiment B1, obtain intermediate B 5.Mass spectrum m/z：477.05 (value of calculation：477.08).Theoretical unit
Cellulose content (%) C28H20BrN3：C,70.30；H,4.21；Br,16.70；N, 8.78 actual measurements constituent content (%)：C,70.32；H,
4.21；Br,16.71；N,8.76.The above results confirm that it is target product to obtain product.
(B6) preparation of intermediate B 6
Bromo- 4 '-the iodo- 1,1 '-biphenyl of 4- in embodiment B1 is replaced with into the iodo- 9,9- diphenyl of the bromo- 7- of equimolar 2-
Fluorenes, other steps are identical with embodiment B1, obtain intermediate B 6.Mass spectrum m/z：601.15 (value of calculation：601.12).Theoretical unit
Cellulose content (%) C38H24BrN3：C,75.75；H,4.01；Br,13.26；N, 6.97 actual measurements constituent content (%)：C,75.74；H,
4.03；Br,13.25；N,6.98.The above results confirm that it is target product to obtain product.
(B7) preparation of intermediate B 7
By the 4- bromo- 4 '-iodo- 1 in embodiment B1,1 '-biphenyl replaces with the iodo- fluorenes of 9,9- spiral shells two of the bromo- 7- of equimolar 2-,
Other steps are identical with embodiment B1, obtain intermediate B 7.Mass spectrum m/z：599.09 (value of calculation：599.10).Theoretical elemental
Content (%) C38H22BrN3：C,76.00；H,3.69；Br,13.31；N, 7.00 actual measurements constituent content (%)：C,76.01；H,
3.67；Br,13.31；N,7.01.The above results confirm that it is target product to obtain product.
(B8) preparation of intermediate B 8
By the 4- bromo- 4 '-iodo- 1 in embodiment B1,1 '-biphenyl replaces with the bromo- 2- iodoethylenes of equimolar 1-, other steps
It is rapid identical with embodiment B1, obtain intermediate B 7.Mass spectrum m/z：311.04 (value of calculation：311.01).Theoretical elemental content
(%) C15H10BrN3：C,57.71；H,3.23；Br,25.60；N, 13.46 actual measurements constituent content (%)：C,57.73；H,3.21；
Br,25.61；N,13.45.The above results confirm that it is target product to obtain product.
Embodiment C：
(C1) synthesis of compound TM1：
By tri-butyl phosphine (toluene solution of the 1.0M of 3mL, 7.32mmol), palladium (0.4g, 1.83mmol) and uncle
Sodium butoxide (22.8g, 238mmol) adds to intermediate B 2 (66.0g, 183mmol) and intermediate A 1 (51.8g, 201mmol) and exists
Solution in degassed toluene (500mL), and the mixture is heated under reflux 2 hours.The reactant mixture is cooled to
Room temperature, filters with dilution with toluene and via kieselguhr.By the filtrate water dilution, and methylbenzene extraction is used, and merge organic
Phase, it is evaporated under vacuo.The residue is filtered via silica gel, target product TM1 is recrystallized to give
(76.7g, theoretical value 80%).
Mass spectrum m/z：524.25 (value of calculation：524.20).Theoretical elemental content (%) C37H24N4：C,84.71；H,4.61；
N, 10.68 actual measurements constituent content (%)：C,84.72；H,4.62；N,10.66.The above results confirm to obtain product for target product
Product.
Following compound is obtained in a similar fashion：
Embodiment C2:Mass spectrum m/z：574.25 (value of calculation：574.22).Theoretical elemental content (%) C41H26N4：C,
85.69；H,4.56；N, 9.75 actual measurements constituent content (%)：C,85.67；H,4.55；N,9.77.The above results confirm to be produced
Thing is target product.
Embodiment C3:Mass spectrum m/z：600.23 (value of calculation：600.23).Theoretical elemental content (%) C43H28N4：C,
85.98；H,4.70；N, 9.33 actual measurements constituent content (%)：C,85.96；H,4.71；N,9.33.The above results confirm to be produced
Thing is target product.
Embodiment C4:Mass spectrum m/z：600.25 (value of calculation：600.23).Theoretical elemental content (%) C43H28N4：C,
85.98；H,4.70；N, 9.33 actual measurements constituent content (%)：C,85.96；H,4.72；N,9.32.The above results confirm to be produced
Thing is target product.
Embodiment C5:Mass spectrum m/z：650.23 (value of calculation：650.25).Theoretical elemental content (%) C47H30N4：C,
86.74；H,4.65；N, 8.61 actual measurements constituent content (%)：C,86.73；H,4.65；N,8.62.The above results confirm to be produced
Thing is target product.
Embodiment C6:Mass spectrum m/z：676.25 (value of calculation：676.26).Theoretical elemental content (%) C49H32N4：C,
86.96；H,4.77；N, 8.28 actual measurements constituent content (%)：C,86.95；H,4.77；N,8.28.The above results confirm to be produced
Thing is target product.
Embodiment C7:Mass spectrum m/z：624.27 (value of calculation：624.23).Theoretical elemental content (%) C45H28N4：C,
86.51；H,4.52；N, 8.97 actual measurements constituent content (%)：C,86.51；H,4.51；N,8.98.The above results confirm to be produced
Thing is target product.
Embodiment C8:Mass spectrum m/z：674.27 (value of calculation：674.25).Theoretical elemental content (%) C49H30N4：C,
87.22；H,4.48；N, 8.30 actual measurements constituent content (%)：C,87.22；H,4.47；N,8.31.The above results confirm to be produced
Thing is target product.
Embodiment C9:Mass spectrum m/z：700.25 (value of calculation：700.26).Theoretical elemental content (%) C51H32N4：C,
87.40；H,4.60；N, 7.99 actual measurements constituent content (%)：C,87.41；H,4.61；N,7.98.The above results confirm to be produced
Thing is target product.
Embodiment C10:Mass spectrum m/z：574.23 (value of calculation：574.22).Theoretical elemental content (%) C41H26N4：C,
85.69；H,4.56；N, 9.75 actual measurements constituent content (%)：C,85.67；H,4.57；N,9.76.The above results confirm to be produced
Thing is target product.
Embodiment C11:Mass spectrum m/z：624.27 (value of calculation：624.23).Theoretical elemental content (%) C45H28N4：C,
86.51；H,4.52；N, 8.97 actual measurements constituent content (%)：C,86.51；H,4.53；N,8.96.The above results confirm to be produced
Thing is target product.
Embodiment C12:Mass spectrum m/z：650.21 (value of calculation：650.25).Theoretical elemental content (%) C47H30N4：C,
86.74；H,4.65；N, 8.61 actual measurements constituent content (%)：C,86.74；H,4.64；N,8.62.The above results confirm to be produced
Thing is target product.
Embodiment C13:Mass spectrum m/z：640.25 (value of calculation：640.26).Theoretical elemental content (%) C46H32N4：C,
86.22；H,5.03；N, 8.74 actual measurements constituent content (%)：C,86.23；H,5.04；N,8.74.The above results confirm to be produced
Thing is target product.
Embodiment C14:Mass spectrum m/z：690.22 (value of calculation：690.28).Theoretical elemental content (%) C50H34N4：C,
86.93；H,4.96；N, 8.11 actual measurements constituent content (%)：C,86.92；H,4.96；N,8.12.The above results confirm to be produced
Thing is target product.
Embodiment C15:Mass spectrum m/z：716.25 (value of calculation：716.29).Theoretical elemental content (%) C52H36N4：C,
87.12；H,5.06；N, 7.82 actual measurements constituent content (%)：C,87.11；H,5.07；N,7.82.The above results confirm to be produced
Thing is target product.
Embodiment C16:Mass spectrum m/z：764.22 (value of calculation：764.29).Theoretical elemental content (%) C56H36N4：C,
87.93；H,4.74；N, 7.32 actual measurements constituent content (%)：C,87.94；H,4.74；N,7.32.The above results confirm to be produced
Thing is target product.
Embodiment C17:Mass spectrum m/z：814.33 (value of calculation：814.31).Theoretical elemental content (%) C60H38N4：C,
88.43；H,4.70；N, 6.87 actual measurements constituent content (%)：C,88.42；H,4.72；N,6.86.The above results confirm to be produced
Thing is target product.
Embodiment C18:Mass spectrum m/z：840.30 (value of calculation：840.33).Theoretical elemental content (%) C62H40N4：C,
88.54；H,4.79；N, 6.66 actual measurements constituent content (%)：C,88.55；H,4.79；N,6.66.The above results confirm to be produced
Thing is target product.
Embodiment C19:Mass spectrum m/z：762.26 (value of calculation：762.28).Theoretical elemental content (%) C56H34N4：C,
88.16；H,4.49；N, 7.34 actual measurements constituent content (%)：C,88.15；H,4.50；N,7.35.The above results confirm to be produced
Thing is target product.
Embodiment C20:Mass spectrum m/z：812.27 (value of calculation：812.29).Theoretical elemental content (%) C60H36N4：C,
88.64；H,4.46；N, 6.89 actual measurements constituent content (%)：C,88.64；H,4.47；N,6.88.The above results confirm to be produced
Thing is target product.
Embodiment C21:Mass spectrum m/z：838.32 (value of calculation：838.31).Theoretical elemental content (%) C62H38N4：C,
88.76；H,4.57；N, 6.68 actual measurements constituent content (%)：C,88.77；H,4.56；N,6.67.The above results confirm to be produced
Thing is target product.
Embodiment C22:Mass spectrum m/z：474.12 (value of calculation：474.18).Theoretical elemental content (%) C33H22N4：C,
83.52；H,4.67；N, 11.81 actual measurements constituent content (%)：C,83.52；H,4.66；N,11.82.The above results confirm to obtain
Product is target product.
Embodiment C23:Mass spectrum m/z：524.22 (value of calculation：524.20).Theoretical elemental content (%) C37H24N4：C,
84.71；H,4.61；N, 10.68 actual measurements constituent content (%)：C,84.72；H,4.61；N,10.67.The above results confirm to obtain
Product is target product.
Embodiment C24:Mass spectrum m/z：550.21 (value of calculation：550.22).Theoretical elemental content (%) C39H26N4：C,
85.07；H,4.76；N, 10.17 actual measurements constituent content (%)：C,85.08；H,4.75；N,10.17.The above results confirm to obtain
Product is target product.
Contrast Application Example：
The glass plate of the transparent conductive layer supersound process in commercial detergent will be coated with, be rinsed in deionized water,
In acetone：Ultrasonic oil removing, is baked under clean environment and completely removes moisture content in alcohol mixed solvent, clear with ultraviolet light and ozone
Wash, and with mental retardation cation beam bombarded surface.Subsequently the ito substrate after process is put into into evaporated device.One layer is deposited with first
The NPB of 40nm is used as hole transmission layer, followed by the evaporation of luminescent layer, the BD1 of mixing evaporation BH1 and 5%, and evaporation total film thickness is
30nm.Subsequently the Alq3 of evaporation 30nm is subsequently deposited with again 0.5nm LiF as electron transfer layer, subsequently the metal of evaporation 60nm
Al。
Application Example 1
The glass plate of the transparent conductive layer supersound process in commercial detergent will be coated with, be rinsed in deionized water,
In acetone：Ultrasonic oil removing, is baked under clean environment and completely removes moisture content in alcohol mixed solvent, clear with ultraviolet light and ozone
Wash, and with mental retardation cation beam bombarded surface.Subsequently the ito substrate after process is put into into evaporated device.One layer is deposited with first
The compound TM7 of 40nm is used as hole transmission layer, followed by the evaporation of luminescent layer, and the BD1 of mixing evaporation BH1 and 5%, evaporation is total
Thickness is 30nm.Subsequently the Alq3 of evaporation 30nm is subsequently deposited with again 0.5nm LiF as electron transfer layer, is subsequently deposited with 60nm
Metal Al.
Application Example 2
Change the TM7 in Application Example 1 into TM19.
Application Example 3
Change the TM7 in Application Example 1 into TM22.
OLED is produced as follows：
Contrast Application Example：ITO/NPB/BH1:BD1/Alq3/LiF/Al；
Application Example 1：ITO/TM7/BH1:BD1/Alq3/LiF/Al；
Application Example 2：ITO/TM19/BH1:BD1/Alq3/LiF/Al；
Application Example 3：ITO/TM22/BH1:BD1/Alq3/LiF/Al；
Under 1000nits, Nan dian Yao device result is as follows：
| Device | Luminous efficiency | Driving voltage | Life-span (T80) |
| Contrast Application Example | 55.2cd/A | 4.7V | 35hours |
| Application Example 1 | 60.3cd/A | 4.5V | 113hours |
| Application Example 2 | 63.1cd/A | 4.3V | 223hours |
| Application Example 3 | 61.2cd/A | 4.4V | 165hours |
Result above shows that the carbazole analog derivative of the present invention is applied in organic electroluminescence device, especially as
Hole mobile material, shows luminous efficiency height, the advantage of life-span length, is luminous organic material of good performance.
Obviously, the explanation of above example is only intended to help and understands the method for the present invention and its core concept.Should refer to
Go out, for the those of ordinary skill of the technical field, under the premise without departing from the principles of the invention, can also be to this
Bright to carry out some improvement and modification, these are improved and modification is also fallen in the protection domain of the claims in the present invention.
Claims (9)
1. a kind of carbazole analog derivative, it is characterised in that with as led to the structure shown in formula I：
Wherein, R1Unsaturated alkyl, the aryl of substituted or unsubstituted C6-C60, replacement selected from substituted or unsubstituted C2-C4
Or the one kind in condensed ring, the condensed hetero ring of substituted or unsubstituted C8～C60 of unsubstituted C10～C60；R2Selected from replacement or not
One kind in the aryl of substituted C6-C60, the condensed ring of substituted or unsubstituted C10～C60.
2. a kind of carbazole analog derivative according to claim 1, it is characterised in that R1Selected from substituted or unsubstituted C2-C4
Unsaturated alkyl, the aryl of substituted or unsubstituted C6-C30, the condensed ring of substituted or unsubstituted C10～C30, replace or not
One kind in the condensed hetero ring of substituted C8～C30；R2It is aryl selected from substituted or unsubstituted C6-C30, substituted or unsubstituted
One kind in the condensed ring of C10～C30.
3. a kind of carbazole analog derivative according to claim 1, it is characterised in that R1Selected from substituted or unsubstituted C2-C4
Unsaturated alkyl, the aryl of substituted or unsubstituted C6-C18, the condensed ring of substituted or unsubstituted C10～C24 in one kind；
R2One kind in aryl, the condensed ring of substituted or unsubstituted C10～C14 selected from substituted or unsubstituted C6-C12.
4. a kind of carbazole analog derivative according to claim 1, it is characterised in that R1Selected from vinyl, phenyl, naphthyl, anthracene
Base, xenyl, terphenyl, fluorenyl, the fluorenyl of spiral shell two or carbazyl；R2Selected from phenyl, naphthyl or xenyl.
5. a kind of carbazole analog derivative according to claim 1, it is characterised in that the carbazole analog derivative is selected from as follows
Any one in structure shown in TM1～TM24：
6. the preparation method of the carbazole analog derivative described in any one of claim 1-5, it is characterised in that closed by following route
Into obtaining the carbazole analog derivative：
Wherein, R1Unsaturated alkyl, the aryl of substituted or unsubstituted C6-C60, replacement selected from substituted or unsubstituted C2-C4
Or the one kind in condensed ring, the condensed hetero ring of substituted or unsubstituted C8～C60 of unsubstituted C10～C60；R2Selected from replacement or not
One kind in the aryl of substituted C6-C60, the condensed ring of substituted or unsubstituted C10～C60.
7. application of the carbazole analog derivative described in claim 1-5 any one in organic electroluminescence device.
8. application of the carbazole analog derivative according to right wants 7 in organic electroluminescence device, it is characterised in that described
Organic electroluminescence device includes anode, negative electrode and organic matter layer, and any one of Claims 1 to 5 is contained in the organic matter layer
Described carbazole analog derivative.
9. application of the carbazole analog derivative according to claim 8 in organic electroluminescence device, it is characterised in that institute
Carbazole analog derivative is stated for preparing the hole transmission layer of organic electroluminescence device.
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