JP4077796B2 - ビフェニル誘導体及びこれを採用した有機電界発光素子 - Google Patents
ビフェニル誘導体及びこれを採用した有機電界発光素子 Download PDFInfo
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- JP4077796B2 JP4077796B2 JP2004000680A JP2004000680A JP4077796B2 JP 4077796 B2 JP4077796 B2 JP 4077796B2 JP 2004000680 A JP2004000680 A JP 2004000680A JP 2004000680 A JP2004000680 A JP 2004000680A JP 4077796 B2 JP4077796 B2 JP 4077796B2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title claims description 39
- 238000005401 electroluminescence Methods 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 134
- 239000000126 substance Substances 0.000 claims description 75
- 239000000463 material Substances 0.000 claims description 55
- 239000002019 doping agent Substances 0.000 claims description 11
- 229910052741 iridium Inorganic materials 0.000 claims description 9
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical group [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 5
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical group C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 description 48
- 125000004432 carbon atom Chemical group C* 0.000 description 47
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 238000004519 manufacturing process Methods 0.000 description 30
- 230000015572 biosynthetic process Effects 0.000 description 29
- 238000003786 synthesis reaction Methods 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 25
- -1 alkoxy halogen compound Chemical class 0.000 description 22
- 125000003118 aryl group Chemical group 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- 150000004696 coordination complex Chemical class 0.000 description 18
- 239000010408 film Substances 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 238000000103 photoluminescence spectrum Methods 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000010409 thin film Substances 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 13
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000010586 diagram Methods 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 238000000862 absorption spectrum Methods 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000004528 spin coating Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000007086 side reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 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 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- 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 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- HTDQSWDEWGSAMN-UHFFFAOYSA-N 1-bromo-2-methoxybenzene Chemical compound COC1=CC=CC=C1Br HTDQSWDEWGSAMN-UHFFFAOYSA-N 0.000 description 2
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- 238000004140 cleaning Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 238000011156 evaluation Methods 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
- 150000004820 halides Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 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
- 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
- HPGNGICCHXRMIP-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dithiine Chemical compound S1CCSC2=CSC=C21 HPGNGICCHXRMIP-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- USMRYMUZKSMTRL-UHFFFAOYSA-N 2-methyl-1,3,2-dioxaborolane Chemical compound CB1OCCO1 USMRYMUZKSMTRL-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- LTBWKAYPXIIVPC-UHFFFAOYSA-N 3-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC(Br)=CC=C3NC2=C1 LTBWKAYPXIIVPC-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C1C2=CCCC=C22)C=CC=C1N2c(cc1-c(cc(cc2)N3c4ccccc4C4=CC=CCC34)c2OI)ccc1O* Chemical compound CC(C1C2=CCCC=C22)C=CC=C1N2c(cc1-c(cc(cc2)N3c4ccccc4C4=CC=CCC34)c2OI)ccc1O* 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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000013461 design 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
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 230000009477 glass transition Effects 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
- 230000005283 ground state Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011254 layer-forming composition Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 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
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000001953 recrystallisation Methods 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 238000004809 thin layer chromatography 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
-
- 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
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/92—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring
-
- 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
-
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Description
R1及びR2は、相互に関係なく、水素原子と、炭素数1〜20の線形(直鎖)または分枝形(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、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一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の線形(直鎖)または分枝形(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、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一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のうち少なくとも一つ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)、単一結合(simple chemical bond;結合子)または−(CH2)n−(ここでnは0〜2の整数であり)、−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の線形(直鎖)または分枝形(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、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一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、及びA7とA8のうち少なくとも一つ、好ましくはA1とA2、A3とA4、A5とA6、及びA7とA8のうち少なくとも一つは、相互に連結されうる。
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の線形(直鎖)または分枝形(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、及びハロゲン原子、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一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、及び炭素数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(A)の製造
2−ブロモアニソール40g(214mmol)を無水THF(246mL)に溶解した後、これを−75℃に冷却してn−ブチルリチウム103mL(1.2eq)を徐々に添加し、1時間攪拌した。前記混合物に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51.8g(1.3eq)を添加して1時間反応させた。
化合物(A)10.3g(44mmol)及び2−ブロモアニソール7.5g(1.1eq)を無水トルエン(29mL)とTHF(29mL)とに溶かした後、2M Na2CO3水溶液89mLを添加して100℃で36時間反応させた。
化合物(B)8g(37.4mmol)をクロロホルム100mLに溶かした後、0℃に維持しつつBr215g(5eq)を徐々に添加した。化合物(B)が完全に除去されれば、Br2の添加を中止し、10分間攪拌した後に反応混合物に少量のアセトンを添加して反応を中止させた。次いで、反応混合物をH2OとCHCl3とを使用して抽出を実施した。抽出によって有機層を集めた後、これをMgSO4で乾燥させた後に濃縮させて、n−ヘキサンで再結晶することによって化合物(C)を収得した。化合物(C)の構造は、1H−NMRを通じて確認した。
化合物(C)4g(10.8mmole)とカルバゾール3.63g(2.02eq)とを無水トルエン(70mL)に溶かし、ここにソジウムtert−ブトキシド3.1g(3eq)、トリ(tert−ブチル)ホスフィン0.11g(0.05eq)及び触媒として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。) 0.4g(0.04eq)を添加して120℃で48時間反応させた。
化合物(C)3g(8.1mmole)とN−フェニル−1−ナフタルアミン3.57g(2.02eq)とを無水トルエン(70mL)に溶かし、ソジウムtert−ブトキシド2.35g(3eq)、トリ(tert−ブチル)ホスフィン0.08g(0.05eq)、そして触媒としてPd2(dba)3 0.3g(0.04eq)を添加して120℃で48時間反応させた。
1)化合物(D)の製造
2−ブロモフェノール50g(290mmol)をアセトン(500mL)に溶かし、K2CO3 48.4g(350mmol)を添加した。次いで、前記反応混合物に1−ブロモオクタン73.3g(380mmol)を添加して24時間還流させた。
化合物(D)38g(130mmol)を無水THF(150mL)に溶解し、反応混合物を−75℃に冷却した後、ここにn−ブチルリチウム100mL(1.2eq)を徐々に添加し、1時間攪拌した。次いで、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)を添加して1時間反応させた。
化合物(E)20g(70mmol)と化合物(D)25g(1.1eq)とを無水トルエン(100mL)に溶かした後、ここに2M Na2CO3水溶液150mLを添加して100℃で36時間反応させた。
化合物(F)10g(24.4 mmol)をCHCl3 150mLに溶かした後、反応混合物を0℃に維持しつつBr28.3g(2.1eq)を徐々に添加した。
化合物(G)4g(7.04 mmole)とカルバゾール2.38g(2.02eq)とを無水トルエン(70mL)に溶かし、ソジウムtert−ブトキシド2.03g(3eq)、トリ(tert−ブチル)ホスフィン0.07g(0.05eq)、そして触媒としてPd2(dba)3を0.26g(0.04eq)を添加して120℃で48時間反応させた。
化合物(G)4g(7.04mmole)とジフェニルアミン2.41g(2.02eq)を無水トルエン(70mL)に溶かし、ソジウムtert−ブトキシド2.03g(3eq)、トリ(tert−ブチル)ホスフィン0.07g(0.05eq)、及び触媒としてPd2(dba)3を0.26g(0.04eq)を添加して120℃で48時間反応させた。
1)化合物(H)の製造
1−ブロモ−4−tert−ブチルベンゼン47.5g(0.223mol)を無水THF500mlに溶かした後、反応混合物を−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分間攪拌させた後、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、反応混合物を約1時間攪拌した。
9−H−3,3−ブロモカルバゾール70g(0.22mol)をTHF 1Lに溶解した。次いで、反応混合物に(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)とを添加した後、常温で約12時間攪拌した。
化合物(H)49g(0.188mol)と化合物(I)24g(0.055mol)とをトルエン300ml及び蒸溜水200mlに添加し、Pd(OAc)2(パラジウムアセテート) 1.2g(5.5mol)とK2CO3 53gとを添加して70℃で16時間攪拌した。
化合物(G)1.2g(2.1mmole)と化合物(J)1.87g(2.05eq)とを無水トルエン(40mL)に溶かしてソジウムtert−ブトキシド0.61g(3eq)、トリ(tert−ブチル)ホスフィン0.02g(0.05eq)、及び触媒としてPd2(dba)3 0.084g(0.04eq)を添加して120℃で48時間反応させた。
ITO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ング剤とを利用してパターニングしてITO電極パターンを形成し、これを再びきれいに洗浄した。このように洗浄された結果物上にPEDOT(Batron P 4083,Bayer社)を約500Åの厚さにコーティングした後、180℃で約1時間ベーキングしてHILを形成した。
発光層の形成時、化学式1eで表示される化合物の代わりに化学式1aないし1dで表示される化合物を各々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 ホール輸送膜、
20 透明電極基板。
Claims (5)
- 下記化学式1aないし1eで表示される化合物のうち何れか一つであることを特徴とするビフェニル誘導体;
- 請求項1に記載のビフェニル誘導体を含むリン光ホスト材料。
- 一対の電極間に発光層を含む有機電界発光素子において、
前記発光層が、請求項2に記載のリン光ホスト材料70ないし99.9質量%と、ドーパント0.1ないし30質量%とよりなる有機電界発光素子。 - 前記ドーパントが、イリジウム錯体である、請求項3に記載の有機電界発光素子。
- 前記イリジウム錯体が、Ir(ppy) 3 である、請求項3または4に記載の有機電界発光素子。
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JP4552382B2 (ja) * | 2003-03-06 | 2010-09-29 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子材料、表示装置及び照明装置 |
KR20060018583A (ko) * | 2004-08-25 | 2006-03-02 | 삼성전자주식회사 | 반도체 나노결정을 함유하는 백색 발광 유·무기하이브리드 전기 발광 소자 |
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US6955856B2 (en) | 2005-10-18 |
KR100624406B1 (ko) | 2006-09-18 |
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US20040214040A1 (en) | 2004-10-28 |
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