CN103896966A - 一类阳极修饰薄膜材料及其在电致发光器件中的应用 - Google Patents
一类阳极修饰薄膜材料及其在电致发光器件中的应用 Download PDFInfo
- Publication number
- CN103896966A CN103896966A CN201410153175.6A CN201410153175A CN103896966A CN 103896966 A CN103896966 A CN 103896966A CN 201410153175 A CN201410153175 A CN 201410153175A CN 103896966 A CN103896966 A CN 103896966A
- Authority
- CN
- China
- Prior art keywords
- film
- glass substrate
- quartz crucible
- film material
- starting material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims abstract description 40
- 239000010409 thin film Substances 0.000 title claims abstract description 25
- 238000012986 modification Methods 0.000 title abstract description 7
- 230000004048 modification Effects 0.000 title abstract description 7
- 238000002347 injection Methods 0.000 claims abstract description 30
- 239000007924 injection Substances 0.000 claims abstract description 30
- 239000010408 film Substances 0.000 claims description 82
- 238000002360 preparation method Methods 0.000 claims description 41
- 238000005401 electroluminescence Methods 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- -1 aromatic heterocycle Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000000243 solution Substances 0.000 abstract description 4
- 238000007738 vacuum evaporation Methods 0.000 abstract description 4
- 238000004528 spin coating Methods 0.000 abstract description 2
- 230000005693 optoelectronics Effects 0.000 abstract 1
- 239000010453 quartz Substances 0.000 description 72
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 72
- 239000000758 substrate Substances 0.000 description 68
- 239000011521 glass Substances 0.000 description 67
- 239000007858 starting material Substances 0.000 description 54
- 239000000047 product Substances 0.000 description 49
- 230000000873 masking effect Effects 0.000 description 36
- 238000004458 analytical method Methods 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000002207 thermal evaporation Methods 0.000 description 18
- 230000005540 biological transmission Effects 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 13
- 239000002994 raw material Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000004949 mass spectrometry Methods 0.000 description 12
- 238000001819 mass spectrum Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000002800 charge carrier Substances 0.000 description 6
- 210000003739 neck Anatomy 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 230000027756 respiratory electron transport chain Effects 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 3
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical class O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 description 2
- PNWSHHILERSSLF-UHFFFAOYSA-N 4-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC=C(C(O)=O)C=C1C(O)=O PNWSHHILERSSLF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- QBKSWRVVCFFDOT-UHFFFAOYSA-N gossypol Chemical compound CC(C)C1=C(O)C(O)=C(C=O)C2=C(O)C(C=3C(O)=C4C(C=O)=C(O)C(O)=C(C4=CC=3C)C(C)C)=C(C)C=C21 QBKSWRVVCFFDOT-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WACNXHCZHTVBJM-UHFFFAOYSA-N 1,2,3,4,5-pentafluorobenzene Chemical compound FC1=CC(F)=C(F)C(F)=C1F WACNXHCZHTVBJM-UHFFFAOYSA-N 0.000 description 1
- YPTYLQNUERVVHH-UHFFFAOYSA-N 1,2-bis(bromomethyl)-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(CBr)C(CBr)=C1 YPTYLQNUERVVHH-UHFFFAOYSA-N 0.000 description 1
- BTAKGWBWUAVBGB-UHFFFAOYSA-N 1,2-bis(bromomethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C(CBr)=C1 BTAKGWBWUAVBGB-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical class C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- VFMUXPQZKOKPOF-UHFFFAOYSA-N 2,3,7,8,12,13,17,18-octaethyl-21,23-dihydroporphyrin platinum Chemical compound [Pt].CCc1c(CC)c2cc3[nH]c(cc4nc(cc5[nH]c(cc1n2)c(CC)c5CC)c(CC)c4CC)c(CC)c3CC VFMUXPQZKOKPOF-UHFFFAOYSA-N 0.000 description 1
- SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 1
- KBZDJUHYRBFGDL-UHFFFAOYSA-N 3,4,5,6-tetrafluorocyclohexa-3,5-diene-1,2-dione Chemical class FC1=C(F)C(=O)C(=O)C(F)=C1F KBZDJUHYRBFGDL-UHFFFAOYSA-N 0.000 description 1
- DNIDAYOSPDNUKP-UHFFFAOYSA-N 3-(2-phenylethenyl)benzene-1,2-diamine Chemical compound NC1=CC=CC(C=CC=2C=CC=CC=2)=C1N DNIDAYOSPDNUKP-UHFFFAOYSA-N 0.000 description 1
- XMPPBZUHDDHOME-UHFFFAOYSA-N 4,5-dioxocyclohexa-2,6-diene-1,2-dicarbonitrile Chemical class O=C1C=C(C#N)C(C#N)=CC1=O XMPPBZUHDDHOME-UHFFFAOYSA-N 0.000 description 1
- SLVJFJMQJYCWFK-UHFFFAOYSA-N 4-(trifluoromethyl)cyclohexa-3,5-diene-1,2-dione Chemical class FC(C1=CC(C(C=C1)=O)=O)(F)F SLVJFJMQJYCWFK-UHFFFAOYSA-N 0.000 description 1
- PXKIKNFPTRUELE-UHFFFAOYSA-N 5,8-dioxonaphthalene-2,3-dicarbonitrile Chemical compound C(#N)C=1C=C2C(C=CC(C2=CC=1C#N)=O)=O PXKIKNFPTRUELE-UHFFFAOYSA-N 0.000 description 1
- XUGYJWSZRANJOP-UHFFFAOYSA-N 6-(trifluoromethyl)naphthalene-1,4-dione Chemical class O=C1C=CC(=O)C2=CC(C(F)(F)F)=CC=C21 XUGYJWSZRANJOP-UHFFFAOYSA-N 0.000 description 1
- XDIWXFTZTJQXDE-UHFFFAOYSA-N 6-nitronaphthalene-1,4-dione Chemical compound O=C1C=CC(=O)C2=CC([N+](=O)[O-])=CC=C21 XDIWXFTZTJQXDE-UHFFFAOYSA-N 0.000 description 1
- 241000024287 Areas Species 0.000 description 1
- GWTWHGRUVIHCIQ-UHFFFAOYSA-N CC1(C(C2=C3NC(C)(C=C(C(F)(F)F)C=C4)C4=N2)=C(C#N)C#N)NSN=C1C3=C(C#N)C#N Chemical compound CC1(C(C2=C3NC(C)(C=C(C(F)(F)F)C=C4)C4=N2)=C(C#N)C#N)NSN=C1C3=C(C#N)C#N GWTWHGRUVIHCIQ-UHFFFAOYSA-N 0.000 description 1
- LHUPLDLZYKXEEN-UHFFFAOYSA-N Cc(cc1C(c2n[s]nc22)=C(C#N)C#N)ccc1C2=C(C#N)C#N Chemical compound Cc(cc1C(c2n[s]nc22)=C(C#N)C#N)ccc1C2=C(C#N)C#N LHUPLDLZYKXEEN-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- SFVMTBLHNSZLKX-UHFFFAOYSA-N N#CC(C#N)=C(c1n[s]nc1C(c1c2)=C(C#N)C#N)c1cc(C#N)c2C#N Chemical compound N#CC(C#N)=C(c1n[s]nc1C(c1c2)=C(C#N)C#N)c1cc(C#N)c2C#N SFVMTBLHNSZLKX-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QHOPXUFELLHKAS-UHFFFAOYSA-N Thespesin Natural products CC(C)c1c(O)c(O)c2C(O)Oc3c(c(C)cc1c23)-c1c2OC(O)c3c(O)c(O)c(C(C)C)c(cc1C)c23 QHOPXUFELLHKAS-UHFFFAOYSA-N 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 229930000755 gossypol Natural products 0.000 description 1
- 229950005277 gossypol Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 235000007715 potassium iodide Nutrition 0.000 description 1
- 229960004839 potassium iodide Drugs 0.000 description 1
- 230000005610 quantum mechanics Effects 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/14—Thiadiazoles; Hydrogenated thiadiazoles condensed with carbocyclic rings or ring systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Physical Vapour Deposition (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410153175.6A CN103896966B (zh) | 2014-04-16 | 2014-04-16 | 一类阳极修饰薄膜材料及其在电致发光器件中的应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410153175.6A CN103896966B (zh) | 2014-04-16 | 2014-04-16 | 一类阳极修饰薄膜材料及其在电致发光器件中的应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103896966A true CN103896966A (zh) | 2014-07-02 |
CN103896966B CN103896966B (zh) | 2016-08-24 |
Family
ID=50988582
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410153175.6A Active CN103896966B (zh) | 2014-04-16 | 2014-04-16 | 一类阳极修饰薄膜材料及其在电致发光器件中的应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN103896966B (zh) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105918772A (zh) * | 2016-05-30 | 2016-09-07 | 华南理工大学 | 一类羧甲基赖氨酸消除剂及其应用 |
CN108264463A (zh) * | 2016-12-30 | 2018-07-10 | 浙江省诸暨合力化学对外贸易有限公司 | 一种制备2-芳基丙二酸衍生物的方法及其应用 |
CN109860397A (zh) * | 2019-03-27 | 2019-06-07 | 南方科技大学 | 光探测器件及光探测器 |
US11950507B2 (en) | 2019-12-03 | 2024-04-02 | Beijing Summer Sprout Technology Co., Ltd. | Organic electroluminescence device |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0346842A1 (en) * | 1988-06-13 | 1989-12-20 | Mitsubishi Oil Company, Limited | Process for separating 2,6-dimethylnaphthalene |
US5102757A (en) * | 1988-09-13 | 1992-04-07 | Fuji Xerox Co., Ltd. | Electrophotographic photosensitive member and image forming process |
JP2002216970A (ja) * | 2001-01-17 | 2002-08-02 | Fuji Xerox Co Ltd | 有機電界発光素子 |
-
2014
- 2014-04-16 CN CN201410153175.6A patent/CN103896966B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0346842A1 (en) * | 1988-06-13 | 1989-12-20 | Mitsubishi Oil Company, Limited | Process for separating 2,6-dimethylnaphthalene |
US5102757A (en) * | 1988-09-13 | 1992-04-07 | Fuji Xerox Co., Ltd. | Electrophotographic photosensitive member and image forming process |
JP2002216970A (ja) * | 2001-01-17 | 2002-08-02 | Fuji Xerox Co Ltd | 有機電界発光素子 |
Non-Patent Citations (2)
Title |
---|
TSUBATA, YOSHIAKI ET AL.: "Tetracyanoquinodimethanes fused with 1,2,5-thiadiazole and pyrazine units", 《HETEROCYCLES》 * |
TSUBATA, YOSHIAKI ET AL.: "Tetracyanoquinodimethanes fused with 1,2,5-thiadiazole and pyrazine units", 《HETEROCYCLES》, vol. 33, no. 1, 31 December 1992 (1992-12-31) * |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105918772A (zh) * | 2016-05-30 | 2016-09-07 | 华南理工大学 | 一类羧甲基赖氨酸消除剂及其应用 |
CN105918772B (zh) * | 2016-05-30 | 2020-01-14 | 华南理工大学 | 一类羧甲基赖氨酸消除剂及其应用 |
CN108264463A (zh) * | 2016-12-30 | 2018-07-10 | 浙江省诸暨合力化学对外贸易有限公司 | 一种制备2-芳基丙二酸衍生物的方法及其应用 |
CN108264463B (zh) * | 2016-12-30 | 2021-04-09 | 浙江省诸暨合力化学对外贸易有限公司 | 一种制备2-芳基丙二酸衍生物的方法及其应用 |
CN109860397A (zh) * | 2019-03-27 | 2019-06-07 | 南方科技大学 | 光探测器件及光探测器 |
CN109860397B (zh) * | 2019-03-27 | 2024-01-26 | 南方科技大学 | 光探测器件及光探测器 |
US11950507B2 (en) | 2019-12-03 | 2024-04-02 | Beijing Summer Sprout Technology Co., Ltd. | Organic electroluminescence device |
Also Published As
Publication number | Publication date |
---|---|
CN103896966B (zh) | 2016-08-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102933531B (zh) | 新有机电致发光化合物和使用该化合物的有机电致发光器件 | |
CN105153130B (zh) | 三嗪类衍生物电子传输化合物及其有机电致发光器件 | |
CN102617477B (zh) | 菲并咪唑衍生物及其作为电致发光材料的应用 | |
WO2020082601A1 (zh) | 深红光热活化延迟荧光材料及其合成方法、电致发光器件 | |
CN109336772A (zh) | 一种含螺结构的三芳香胺化合物及其用途和发光器件 | |
CN107721979A (zh) | 一种基于吡啶和三嗪的有机电致发光化合物及其有机电致发光器件 | |
Huang et al. | Unsymmetrically amorphous 9, 10-disubstituted anthracene derivatives for high-efficiency blue organic electroluminescence devices | |
CN109970642A (zh) | 双极性热活化延迟荧光材料及其制备方法与有机电致发光二极管器件 | |
CN107056807B (zh) | 一种以均苯为核心的化合物及其在有机电致发光器件中的应用 | |
CN103896966B (zh) | 一类阳极修饰薄膜材料及其在电致发光器件中的应用 | |
WO2023165079A1 (zh) | 一种双吡啶吩嗪热激活延迟荧光材料掺杂的白光电致发光器件 | |
CN110272377B (zh) | 红绿蓝热活化延迟荧光材料,其合成方法及应用 | |
CN105566399B (zh) | 铱配合物及其制备方法和应用该铱配合物的有机电致发光器件 | |
CN110041268A (zh) | 一种嘧啶类双极性化合物及其在oled器件中的应用 | |
CN102050798B (zh) | 2-(2’-羟基苯基)-苯并噻唑衍生物发光材料 | |
CN108752317A (zh) | 一种含蒽衍生物及其用途和发光器件 | |
WO2020237885A1 (zh) | 深蓝色热活化延迟荧光材料和其制备方法、电致发光器件 | |
JP2014208602A (ja) | 新規イミダゾール化合物、電子デバイス用材料、発光素子、電子デバイス及びその製造方法 | |
CN101597255B (zh) | 一种有机材料及其在有机电致发光器件中的应用 | |
CN116120349B (zh) | 一种硼氮化合物及其制备方法和应用 | |
CN106554358B (zh) | 一种具有螺结构的有机电致发光化合物及其发光器件 | |
CN109232495A (zh) | 一种含茚并噻吩和呋喃的三芳香胺化合物及发光器件 | |
Ouyang et al. | Design and synthesis of 2-substituted-8-hydroxyquinline zinc complexes with hole-transporting ability for highly effective yellow-light emitters | |
CN108976196A (zh) | 一种含五元环螺结构的芳香胺化合物及其用途和发光器件 | |
CN107501101A (zh) | 一种含萘并茚芴单元的有机发光小分子材料及其制备方法与应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20170822 Address after: Room 5, building A, zone, No. 2499, Wei Shan Road, high tech Zone, Changchun, Jilin, China Patentee after: Jilin University Science Park Development Center Address before: 130012 Changchun Qianjin Street, Jilin, No. 2699 Patentee before: Jilin University |
|
TR01 | Transfer of patent right |
Effective date of registration: 20170928 Address after: 130012 Jilin province Changchun high tech District No. 3333 North Street North Grand Changchun science and technology park a first floor of building C2-1 Patentee after: Jilin Jida Incubator Co. Ltd. Address before: Room 5, building A, zone, No. 2499, Wei Shan Road, high tech Zone, Changchun, Jilin, China Patentee before: Jilin University Science Park Development Center |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20171120 Address after: 130000 Jilin province Changchun Beihu Sheng Technology Development Zone No. 3333 North Street North Lake Science and technology park a B1-1 8 storey building 801 room 002 block Patentee after: Jilin meta synthetic electronic material Limited by Share Ltd Address before: 130012 Jilin province Changchun high tech District No. 3333 North Street North Grand Changchun science and technology park a first floor of building C2-1 Patentee before: Jilin Jida Incubator Co. Ltd. |
|
TR01 | Transfer of patent right | ||
CP01 | Change in the name or title of a patent holder |
Address after: 130000 Jilin province Changchun Beihu Sheng Technology Development Zone No. 3333 North Street North Lake Science and technology park a B1-1 8 storey building 801 room 002 block Patentee after: Jilin Yuanhe Electronic Material Co.,Ltd. Address before: 130000 Jilin province Changchun Beihu Sheng Technology Development Zone No. 3333 North Street North Lake Science and technology park a B1-1 8 storey building 801 room 002 block Patentee before: Jilin meta synthetic electronic material Limited by Share Ltd. |
|
CP01 | Change in the name or title of a patent holder |