JP4077797B2 - ジフェニルアントラセン誘導体及びそれを採用した有機電界発光素子 - Google Patents
ジフェニルアントラセン誘導体及びそれを採用した有機電界発光素子 Download PDFInfo
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- JP4077797B2 JP4077797B2 JP2004000681A JP2004000681A JP4077797B2 JP 4077797 B2 JP4077797 B2 JP 4077797B2 JP 2004000681 A JP2004000681 A JP 2004000681A JP 2004000681 A JP2004000681 A JP 2004000681A JP 4077797 B2 JP4077797 B2 JP 4077797B2
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- FCNCGHJSNVOIKE-UHFFFAOYSA-N 9,10-diphenylanthracene Chemical class C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 FCNCGHJSNVOIKE-UHFFFAOYSA-N 0.000 title claims description 31
- 238000005401 electroluminescence Methods 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 77
- 125000004432 carbon atom Chemical group C* 0.000 claims description 55
- 239000000126 substance Substances 0.000 claims description 54
- 239000000463 material Substances 0.000 claims description 29
- 238000002347 injection Methods 0.000 claims description 24
- 239000007924 injection Substances 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- -1 poly (p-phenylene vinylene) Polymers 0.000 claims description 16
- 230000005525 hole transport Effects 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229920000553 poly(phenylenevinylene) Polymers 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 229920000412 polyarylene Polymers 0.000 claims description 2
- 229920002098 polyfluorene Polymers 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 94
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000004519 manufacturing process Methods 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- 238000000034 method Methods 0.000 description 19
- 229920000291 Poly(9,9-dioctylfluorene) Polymers 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- 230000001629 suppression Effects 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000010408 film Substances 0.000 description 11
- 125000001072 heteroaryl group Chemical group 0.000 description 11
- 239000010409 thin film Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000004528 spin coating Methods 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229920000547 conjugated polymer Polymers 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 2
- MRWWWZLJWNIEEJ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane Chemical compound CC(C)OB1OC(C)(C)C(C)(C)O1 MRWWWZLJWNIEEJ-UHFFFAOYSA-N 0.000 description 2
- BRUOAURMAFDGLP-UHFFFAOYSA-N 9,10-dibromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=C(Br)C2=C1 BRUOAURMAFDGLP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 1
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- XHCAGOVGSDHHNP-UHFFFAOYSA-N 1-bromo-4-tert-butylbenzene Chemical compound CC(C)(C)C1=CC=C(Br)C=C1 XHCAGOVGSDHHNP-UHFFFAOYSA-N 0.000 description 1
- HPGNGICCHXRMIP-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dithiine Chemical compound S1CCSC2=CSC=C21 HPGNGICCHXRMIP-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- NLCSYTQMIMSIGC-UHFFFAOYSA-N 4-octoxy-3-[10-[2-octoxy-5-(n-phenylanilino)phenyl]anthracen-9-yl]-n,n-diphenylaniline Chemical compound CCCCCCCCOC1=CC=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1C(C1=CC=CC=C11)=C2C=CC=CC2=C1C(C(=CC=1)OCCCCCCCC)=CC=1N(C=1C=CC=CC=1)C1=CC=CC=C1 NLCSYTQMIMSIGC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229920000109 alkoxy-substituted poly(p-phenylene vinylene) Polymers 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000011254 layer-forming composition Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- JNBXWZGMEVQJTH-UHFFFAOYSA-N n,n-diphenylaniline;3-methyl-n-phenylaniline Chemical compound CC1=CC=CC(NC=2C=CC=CC=2)=C1.C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 JNBXWZGMEVQJTH-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical class C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000327 poly(triphenylamine) polymer Polymers 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 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 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
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Description
R1とR2は、相互に関係なく、炭素数1〜20の線型または分枝型アルキル基であり、
前記化学式1の−N(Ar 1 )(Ar 2 )または−N(Ar 3 )(Ar 4 )は、相互独立的に、下記化学式2または化学式(2a)で表示される基である、
A 1 、A 2 、A 3 、A 4 、A 5 、A 6 、A 7 及びA 8 は、相互に関係なく、水素原子または炭素数1〜10のアルキル基を有する炭素数6〜20のアリール基である。
R1とR2は、相互に関係なく、水素原子と、炭素数1〜20の線型(直鎖)または分枝型(分岐鎖)アルキル基と、炭素数5〜20のシクロアルキル基と、炭素数6〜20のアリール基と、炭素数4〜20のヘテロアリール基と、または、ハロゲン原子、炭素数1〜10のハロゲン化されたアルキル基、−Si(R)(R’)(R”)、炭素数1〜10のアルキル基、炭素数1〜10のアルコキシ基、炭素数6〜10のアリール基、炭素数4〜10のヘテロアリール基、−N(R)(R’)の中から選択された1つ以上の置換基を有する炭素数6〜20のアリール基と、よりなる群から選択され、
Ar1、Ar2、Ar3及びAr4は、相互に関係なく、水素原子と、炭素数1〜20の線型(直鎖)または分枝型(分岐鎖)アルキル基と、炭素数5〜20のシクロアルキル基と、炭素数6〜20のアリール基と、炭素数4〜20のヘテロアリール基と、または、ハロゲン原子、炭素数1〜10のハロゲン化されたアルキル基、−Si(R)(R’)(R”)、炭素数1〜10のアルキル基、炭素数1〜10のアルコキシ基、炭素数6〜10のアリール基、炭素数4〜10のヘテロアリール基、−N(R)(R’)の中から選択された1つ以上の置換基を有する炭素数6〜20のアリール基と、よりなる群から選択され、
前記Ar1とAr2、Ar3とAr4のうち選択された1つ以上は相互に連結されていてもよく、
前記R、R’及びR”は、相互独立的に、水素原子、炭素数1〜10のアルキル基、炭素数1〜10のアルコキシ基、炭素数6〜10のアリール基、炭素数4〜10のヘテロアリール基よりなる群から選択されてなるものである。
Xは、無結合(後述する化学式(2a)、(2b)参照のこと)、−(CH2)n−(ここでnは、0〜2の整数であり、n=0のときは、結合子(simple chemical bond;単一結合)を意味する。)、−C(R3)(R4)−、−CH=CH−、−S−、−O−または−Si(R3)(R4)−であり、
A1、A2、A3、A4、A5、A6、A7、A8、R3、R4、R5及びR6は、相互に関係なく、水素原子と、炭素数1〜20の線型(直鎖)または分枝型(分岐鎖)アルキル基と、炭素数5〜20のシクロアルキル基と、炭素数6〜20のアリール基と、炭素数4〜20のヘテロアリール基と、ハロゲン原子、炭素数1〜10のハロゲン化されたアルキル基、−Si(R)(R’)(R”)、炭素数1〜10のアルキル基、炭素数1〜10のアルコキシ基、炭素数6〜10のアリール基、炭素数4〜10のヘテロアリール基及び−N(R)(R’)の中から選択された1つ以上の置換基を有する炭素数6〜20のアリール基と、よりなる群から選択され、
前記A1とA2、A2とA3、A3とA4、A5とA6、A6とA7、A7とA8のうちから選択された1つ以上、好ましくはA1とA2、A3とA4、A5とA6、A7とA8のうちから選択された1つ以上は、相互に連結される場合があり、
前記R、R’及びR”は、相互独立的に、水素原子、炭素数1〜10のアルキル基、炭素数1〜10のアルコキシ基、炭素数6〜10のアリール基、炭素数4〜10のヘテロアリール基よりなる群から選択されてなるものである。
B1、B2、B3、B4及びB5は、相互に関係なく、水素原子と、炭素数1〜20の線型(直鎖)または分枝型(分岐鎖)アルキル基と、炭素数5〜20のシクロアルキル基と、炭素数6〜20のアリール基と、炭素数4〜20のヘテロアリール基と、またはハロゲン原子、炭素数1〜10のハロゲン化されたアルキル基、−Si(R)(R’)(R”)、炭素数1〜10のアルキル基、炭素数1〜10のアルコキシ基、炭素数6〜10のアリール基、炭素数4〜10のヘテロアリール基及び−N(R)(R’)の中から選択された1つ以上の置換基を有する炭素数6〜20のアリール基と、よりなる群から選択され、
前記R、R’及びR”は、相互独立的に、水素原子、炭素数1〜10のアルキル基、炭素数1〜10のアルコキシ基、炭素数6〜10のアリール基、炭素数4〜10のヘテロアリール基よりなる群から選択されてなるものである。
1)化合物(1)の製造
2−ブロモフェノール50g(290mmol)をアセトン(500mL)に溶解させ、ここにK2CO3 48.4g(350mmol)を添加した。前記混合物に1−ブロモオクタン 73.3g(380mmol)を添加し、24時間還流させた。
化合物(1)38g(130mmol)を無水THF(150mL)に溶解させた。前記混合物を約−75℃に冷却した後、ここにn−ブチルリチウム(BuLi;Buはブチル基を表す)100mL(1.2eq)を徐々に添加し、1時間撹拌した。前記反応混合物に2−イソプロポキシ−4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン32.9g(1.3eq)を添加し、1時間反応させた。
500mの丸底フラスコに化合物(2)33g(2.3eq)、9,10−ジブロモアントラセン17g(0.05mol)、テトラキストリフェニルフォスフィンパラジウム(0)(Pd(pph3)4)0.87g(1.5mol%vs.9,10−ジブロモアントラセン)及び2M炭酸ナトリウム(Na2CO3)水溶液150mLを入れ、無水トルエン100mLを添加し、固形成分を溶解させた後、100℃で36時間反応させた。
250mの丸底フラスコ内でクロロホルム100mLに化合物(3)5g(8.5mmol)を加えた後、0℃を維持しながらブロム(Br2)2.8g(2.1eq)をゆっくりと添加しながら撹拌した。前記反応混合物から化合物(3)が消えることをTLC(薄層クロマトグラフィ)で確認した後、ブロム添加を中止し、30分間撹拌した後、少量のアセトンを添加してブロム化反応を中止させた。
窒素ガス雰囲気下で、250mLの丸底フラスコに化合物(4)4g(5.37mmol)、9−H−カルバゾール1.98g(11.82mmol)、Pd2(dba)3(tris(dibenzylideneacetone)dipalladium;dbaはジベンジリデンアセトン(dibenzylideneacetone)の略記号である。) 0.197g(2.15×10−4mol)、NaOtBu 1.6g(1.61×10−2mol)、及び(t−Bu)3P 0.0663mL(2.69×10−4mol)を付加した後、ここに無水トルエン100mLに添加した。前記反応混合物の温度をオイルバスを利用して約110℃に上げた後、この温度で反応混合物を約48時間撹拌した。
1)化合物(5)の製造
1−ブロモ−4−t−ブチルベンゼン47.5g(0.223mol)を無水THF500mLに溶かした後、反応混合物の温度を約−70℃まで冷却した。次いで、反応混合物に2.5M n−ブチルリチウム127.4mL(0.3185mol)を徐々に添加し、これを約30分間撹拌した後、2−イソプロポキシ−4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン50mL(0.245mol)を添加して約1時間撹拌した。
9−H−3,3−ジブロモカルバゾール70g(0.22mol)を1Lのフラスコに入れ、THF 1Lを添加して溶かした後、(Boc)2O(Bocは、tert−ブトキシカルボニル基を表す) 56.7g(0.26mol)とDMAP(4−dimethylaminopyridine)3.2g(0.026mol)を添加後、常温で約12時間撹拌した。
化合物(5)49g(0.188mol)と化合物(6)24g(0.055mol)とをトルエン300mLと蒸溜水200mLに添加し、Pd(OAc)2 1.2g(5.5mol)とK2CO3 53gを添加して70℃で16時間撹拌した。
前記反応が終結された後、反応混合物をエチルアセテート400mLで抽出し、減圧濃縮した。得られた残留物を直ちに次の反応に使用した。ここで、化合物(7)の構造は11H−NMRを通じて確認した。
前記過程によって得られた残留物にTFA(Trifluoroacetic acid)30mLとDMF100mLとを添加し、約48時間100℃で撹拌した。
窒素ガス雰囲気下で、100mLの丸底フラスコに化合物(4)1.2g(1.6mmol)、化合物(8)1.426g(3.3mmol)、Pd2(dba)3 0.059g(0.64×10−4mol)、NaOtBu 0.465g(4.835×10−3mol)、そして、(t−Bu)3P 0.016g(0.81×10−4mol)及び無水トルエン40mLを付加した。前記反応混合物の温度をオイルバスを利用して110℃まで上げた後、これを48時間撹拌した。
窒素ガス雰囲気下で、250mLの丸底フラスコに化合物(4)4g(5.37mmol)、N,N−ジフェニルアミン2.00g(11.82mmol)、Pd2(dba)3 0.197g(2.15×10−4mol)、NaOtBu 1.6g(1.61×10−2mol)及び(t−Bu)3P 0.0663mL(2.69×10−4mol)を付加し、無水トルエン100mLを付加した。前記反応混合物の温度をオイルバスを利用して約110℃までゆっくり上げた後、これを48時間撹拌した。
ITO(indium−tin oxide)がコーティングされた透明電極基板をきれいに洗浄した後、ITOを感光性樹脂とエッチェントを利用してパターニングしてITO電極パターンを形成し、これをさらにきれいに洗浄した。このように洗浄された結果物上にPEDOT(poly(styrene sulfonate)−doped poly(3,4−ethylenedioxythiophene:Bayer社のBatron P 4083)を約500Åの厚さにコーティングした後、180℃で約1時間ベイキングしてホール注入層を形成した。
発光層の形成時、10:90混合重量比の代わりに20:80混合重量比の合成例2によって製造された化学式1bの化合物0.02gとPC8F 0.08gとを使用したことを除いては、実施例1と同じ方法によって実施して有機EL素子を完成した。
発光層の形成時、10:90混合重量比の代わりに30:70混合重量比の合成例2によって製造された化学式1bの化合物0.03gとPC8F 0.07gとを使用したことを除いては、実施例1と同じ方法によって実施して有機EL素子を完成した。
発光層の形成時、10:90混合重量比の合成例2によって製造された化学式1bの化合物とPC8Fとの代わりに合成例2によって製造された化学式1bの化合物0.1gのみを使用したことを除いては、実施例1と同じ方法によって実施して有機EL素子を完成した。
発光層の形成時、10:90混合重量比の合成例2によって製造された化学式1bの化合物とPC8Fとの代わりにPC8F 0.1gのみを使用したことを除いては、実施例1と同じ方法によって実施して有機EL素子を完成した。
11 ホール注入層(HIL)、
12 発光層、
13 ホール抑制層(HBL)、
14 第2電極、
15 電子輸送層(ETL)、
16 ホール輸送層、
20 透明電極基板。
Claims (6)
- 下記化学式1で表示されるジフェニルアントラセン誘導体;
R1とR2は、相互に関係なく、炭素数1〜20の線型または分枝型アルキル基であり、
前記化学式1の−N(Ar 1 )(Ar 2 )または−N(Ar 3 )(Ar 4 )は、相互独立的に、下記化学式2または化学式(2a)で表示される基である、
A 1 、A 2 、A 3 、A 4 、A 5 、A 6 、A 7 及びA 8 は、相互に関係なく、水素原子または炭素数1〜10のアルキル基を有する炭素数6〜20のアリール基である。 - 前記化学式1で表示される化合物が、下記化学式1aないし1cで表示される化合物のうちの1つであることを特徴とする請求項1に記載のジフェニルアントラセン誘導体;
- 1対の電極間に有機膜を含む有機電界発光素子において、
前記有機膜が、請求項1または2に記載のジフェニルアントラセン誘導体を含むことを特徴とする有機電界発光素子。 - 前記有機膜が、発光層、ホール注入層またはホール輸送層であることを特徴とする請求項3に記載の有機電界発光素子。
- 前記有機膜が発光層であり、
前記発光層が、請求項1または2のジフェニルアントラセン誘導体0.1ないし99.9質量%と、発光物質99.9ないし0.1質量%と、を含むことを特徴とする請求項3に記載の有機電界発光素子。 - 前記発光物質が、
ポリフルオレン、ポリアリーレン、ポリ(p−フェニレン)またはポリ(p−フェニレンビニレン)よりなる群から選択された1つ以上であることを特徴とする請求項5に記載の有機電界発光素子。
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Families Citing this family (39)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7651787B2 (en) * | 2003-02-19 | 2010-01-26 | Lg Display Co., Ltd. | Organic electroluminescent device |
TWI373506B (en) | 2004-05-21 | 2012-10-01 | Toray Industries | Light-emitting element material and light-emitting material |
GB0417927D0 (en) * | 2004-08-12 | 2004-09-15 | Elam T Ltd | Electroluminescent materials and devices |
KR20060018583A (ko) * | 2004-08-25 | 2006-03-02 | 삼성전자주식회사 | 반도체 나노결정을 함유하는 백색 발광 유·무기하이브리드 전기 발광 소자 |
EP1655359A1 (de) * | 2004-11-06 | 2006-05-10 | Covion Organic Semiconductors GmbH | Organische Elektrolumineszenzvorrichtung |
US7714501B2 (en) * | 2004-12-01 | 2010-05-11 | Semiconductor Energy Laboratory Co., Ltd. | Light emitting element, light emitting device and electronic equipment |
GB0426675D0 (en) * | 2004-12-06 | 2005-01-05 | Elam T Ltd | Electroluminescent materials and devices |
US7351999B2 (en) * | 2004-12-16 | 2008-04-01 | Au Optronics Corporation | Organic light-emitting device with improved layer structure |
US20080001123A1 (en) * | 2004-12-28 | 2008-01-03 | Idemitsu Kosan Co., Ltd | Luminescent Ink Composition for Organic Electroluminescent Device |
WO2006104221A1 (en) * | 2005-03-28 | 2006-10-05 | Semiconductor Energy Laboratory Co., Ltd. | Anthracene derivative, material for light emitting element, light emitting element, light emitting device, and electronic device |
WO2007026587A1 (en) * | 2005-08-29 | 2007-03-08 | Semiconductor Energy Laboratory Co., Ltd. | Anthracene derivative and hole transporting material, light emitting element, and electronic appliance using the same |
JP2007091715A (ja) * | 2005-08-29 | 2007-04-12 | Semiconductor Energy Lab Co Ltd | アントラセン誘導体及びそれを用いた正孔輸送材料、発光素子、発光装置、電子機器 |
WO2007026626A1 (en) * | 2005-08-31 | 2007-03-08 | Semiconductor Energy Laboratory Co., Ltd. | Carbazole derivative, material for light emitting element, light emitting element, light emitting device, and electronic device |
JP5041766B2 (ja) * | 2005-09-02 | 2012-10-03 | 株式会社半導体エネルギー研究所 | アントラセン誘導体、アントラセン誘導体を用いた発光素子、発光装置及び電子機器 |
KR101479924B1 (ko) | 2005-09-02 | 2015-01-12 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 안트라센 유도체 |
US7901793B2 (en) * | 2005-09-23 | 2011-03-08 | Samsung Mobile Display Co., Ltd. | Organic light-emitting compound and organic light-emitting device containing the same |
KR101243918B1 (ko) * | 2006-01-03 | 2013-03-14 | 삼성디스플레이 주식회사 | 청색 발광 고분자, 그 제조방법 및 이를 채용한 유기 전계발광 소자 |
EP1840120B1 (de) * | 2006-03-27 | 2013-04-24 | Novaled AG | N-Heterozyklische Verbindungen und deren Verwendung in elektronischen, optoelektronischen und elektroluminiszenten Bauelementen. |
KR101320382B1 (ko) * | 2006-05-22 | 2013-10-29 | 삼성디스플레이 주식회사 | 유기 발광 화합물 및 이를 구비한 유기 발광 소자 |
CN101506163B (zh) * | 2006-08-30 | 2012-05-02 | 株式会社半导体能源研究所 | 合成蒽衍生物的方法和蒽衍生物、发光元件、发光装置、电子装置 |
WO2008038607A1 (en) | 2006-09-28 | 2008-04-03 | Semiconductor Energy Laboratory Co., Ltd. | Anthracene derivative, and light emitting element, light emitting device, and electronic device using the anthracene derivative |
JP4478166B2 (ja) | 2006-11-09 | 2010-06-09 | 三星モバイルディスプレイ株式會社 | 有機金属錯体を含む有機膜を備えた有機発光素子 |
US7723722B2 (en) | 2007-03-23 | 2010-05-25 | Semiconductor Energy Laboratory Co., Ltd. | Organic compound, anthracene derivative, and light-emitting element, light-emitting device, and electronic device using anthracene derivative |
US20080286445A1 (en) * | 2007-05-17 | 2008-11-20 | Semiconductor Energy Laboratory Co., Ltd. | Composition, and method of fabricating light-emitting element |
JP5352304B2 (ja) * | 2008-04-02 | 2013-11-27 | 株式会社半導体エネルギー研究所 | アントラセン誘導体、発光材料、発光素子用材料、塗布用組成物、発光素子、及び発光装置 |
JP5501656B2 (ja) | 2008-05-16 | 2014-05-28 | 株式会社半導体エネルギー研究所 | 組成物、薄膜の作製方法、及び発光素子の作製方法 |
WO2010005066A1 (en) * | 2008-07-08 | 2010-01-14 | Semiconductor Energy Laboratory Co., Ltd. | Carbazole derivative, light-emitting element material, light-emitting element, and light-emitting device |
KR20110043744A (ko) * | 2008-08-13 | 2011-04-27 | 우베 고산 가부시키가이샤 | 유기 황 화합물 및 그 제조 방법, 그리고 그것을 사용한 유기 전계발광 소자 |
JP5459903B2 (ja) * | 2008-09-02 | 2014-04-02 | 株式会社半導体エネルギー研究所 | アントラセン誘導体、発光素子、発光装置、電子機器、及び照明装置 |
KR101661328B1 (ko) | 2008-09-19 | 2016-09-29 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 카르바졸 유도체 및 그 제조 방법 |
WO2010151654A1 (en) | 2009-06-24 | 2010-12-29 | Cyalume Technologies, Inc. | Blue/violet diphenylanthracene chemiluminescent fluorescers |
US20110143274A1 (en) * | 2009-12-10 | 2011-06-16 | Xerox Corporation | Toner processes |
KR101170220B1 (ko) * | 2009-12-30 | 2012-07-31 | 주식회사 두산 | 트리페닐렌계 화합물 및 이를 포함하는 유기 전계 발광 소자 |
JP6349902B2 (ja) * | 2014-04-16 | 2018-07-04 | Jnc株式会社 | アントラセン誘導体および有機el素子 |
KR102287341B1 (ko) | 2014-08-19 | 2021-08-06 | 삼성디스플레이 주식회사 | 유기 발광 소자 및 이를 포함하는 유기 발광 표시 장치 |
US20160126505A1 (en) * | 2014-10-30 | 2016-05-05 | Nano And Advanced Materials Institute Limited | Solution Process Electron Transporting Layer for Polymer Light Emitting Diode |
KR102318252B1 (ko) * | 2015-01-14 | 2021-10-28 | 삼성디스플레이 주식회사 | 유기 발광 소자 및 이를 포함하는 표시 장치 |
KR20170101128A (ko) | 2016-02-26 | 2017-09-05 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
JP7325731B2 (ja) | 2018-08-23 | 2023-08-15 | 国立大学法人九州大学 | 有機エレクトロルミネッセンス素子 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1208422C (zh) * | 1999-09-21 | 2005-06-29 | 出光兴产株式会社 | 有机电致发光装置和有机发光介质 |
JP4094203B2 (ja) * | 2000-03-30 | 2008-06-04 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子及び有機発光媒体 |
US7053255B2 (en) * | 2000-11-08 | 2006-05-30 | Idemitsu Kosan Co., Ltd. | Substituted diphenylanthracene compounds for organic electroluminescence devices |
DE10228769A1 (de) * | 2002-06-27 | 2004-02-05 | Infineon Technologies Ag | Isoliermaterial für Aluminium und Kupfermetallisierungen |
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