JP4177310B2 - 4,4’−ビス(カルバゾール−9−イル)−ビフェニル系シリコン化合物及びそれを利用した有機電界発光素子 - Google Patents
4,4’−ビス(カルバゾール−9−イル)−ビフェニル系シリコン化合物及びそれを利用した有機電界発光素子 Download PDFInfo
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- JP4177310B2 JP4177310B2 JP2004265417A JP2004265417A JP4177310B2 JP 4177310 B2 JP4177310 B2 JP 4177310B2 JP 2004265417 A JP2004265417 A JP 2004265417A JP 2004265417 A JP2004265417 A JP 2004265417A JP 4177310 B2 JP4177310 B2 JP 4177310B2
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- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group 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 title description 12
- 150000003377 silicon compounds Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 76
- 239000000126 substance Substances 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 239000002019 doping agent Substances 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 238000002347 injection Methods 0.000 claims description 7
- 239000007924 injection Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 230000005525 hole transport Effects 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 5
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 4
- 125000005638 hydrazono group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 2
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 35
- 239000000463 material Substances 0.000 description 22
- 125000001424 substituent group Chemical group 0.000 description 21
- -1 CBP compound Chemical class 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- 238000005424 photoluminescence Methods 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 238000005401 electroluminescence Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000002411 thermogravimetry Methods 0.000 description 8
- 238000000103 photoluminescence spectrum Methods 0.000 description 7
- 238000002076 thermal analysis method Methods 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000005281 excited state Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 5
- 239000004926 polymethyl methacrylate Substances 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 230000005283 ground state Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 3
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000002207 thermal evaporation 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
- 238000002211 ultraviolet spectrum Methods 0.000 description 3
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-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
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000004776 molecular orbital Methods 0.000 description 2
- 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 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 description 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 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
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- MZYDBGLUVPLRKR-UHFFFAOYSA-N 9-(3-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 MZYDBGLUVPLRKR-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- 0 C*1(c2ccccc2-c2c1cccc2)c1cc(*)cc(N(C2C=CC=CC22)c3c2cccc3)c1 Chemical compound C*1(c2ccccc2-c2c1cccc2)c1cc(*)cc(N(C2C=CC=CC22)c3c2cccc3)c1 0.000 description 1
- JYUDEEWCLRYKIX-UHFFFAOYSA-N Cc1cc(-[n]2c3ccccc3c3c2cccc3)cc(-[n]2c3ccccc3c3c2cccc3)c1 Chemical compound Cc1cc(-[n]2c3ccccc3c3c2cccc3)cc(-[n]2c3ccccc3c3c2cccc3)c1 JYUDEEWCLRYKIX-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 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 1
- XRXAVEQCLXHNEH-UHFFFAOYSA-O c(cc1)cc(c2c3cccc2)c1[n]3-c(cc1)ccc1[SH+]c(cc1)ccc1-[n]1c(cccc2)c2c2c1cccc2 Chemical compound c(cc1)cc(c2c3cccc2)c1[n]3-c(cc1)ccc1[SH+]c(cc1)ccc1-[n]1c(cccc2)c2c2c1cccc2 XRXAVEQCLXHNEH-UHFFFAOYSA-O 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 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
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000000109 phenylethoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005554 pyridyloxy group Chemical group 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- 239000011787 zinc oxide Substances 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
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Description
最近、CBPより大きい三重項エネルギーギャップを有するmCP(1,3−ビス(カルバゾール−9−イル)−ベンゼン)化合物が使われているが、この分子は分子量があまりにも小さく、安定性が低い問題点を有している。したがって、高効率長寿命の青色発光特性を得るためには、CBPより三重項エネルギーギャップがさらに大きくて青色ドーパントへのエネルギー転移が効率的で高いTg(ガラス転移温度)を有するホスト材料の確保が非常に重要である。
下記反応式3の反応経路によって化学式4の化合物と化学式5の化合物とを合成した。
カルバゾール(335mg、2mmol)、1,4−ジブロモベンゼン(1.2g、5mmol)、CuI(76mg、0.4mmol)、K2CO3(1.1g、8mmol)及び18−クラウン−6(上記反応式3では、18−C−6と略記した)(10mg、0.04mmol)をDMPU(1,3−ジメチル−3,4,5,6−テトラヒドロ−(1H)−ピリミジノン)(5mL)に溶かした後、175℃で8時間加熱した。前記反応混合物を常温に冷ました後、固体物質を濾過して濾過液に少量のアンモニア水を添加した後、ジエチルエーテル(10mL)で3回洗浄した。洗浄されたジエチルエーテル層をMgSO4で乾燥させた後、減圧乾燥して粗生成物を得、シリカゲルカラムクロマトグラフィで分離、精製して中間体(A’)である480mg(収率75%)の白色の固体を得た。
化学式4の化合物の合成
中間体(A’)(2g、6.29mmol)をTHF(20mL)に溶かした後、−78℃でn−へキサンに溶けているn−ブチルリチウム(上記反応式3では、n−BuLiと記した)(2.75mL、7.2mmol、2.5eqiv.)を一滴ずつ滴下した後、1時間攪拌した。前記反応混合物にジクロロジメチルシラン(上記反応式3では、(CH3)2SiCl2と記した)(0.365mL、3.0mmol)を付加した後、常温で5時間攪拌した。
13CNMR(CDCl3、100MHz)δ(ppm)140.7、138.7、137.1、135.7、126.3、125.9、123.5、120.3、120.0、109.9、−2.2
前記化学式4の化合物をCHCl3に0.2mMの濃度に薄くしてUVスペクトルを得、最大吸収波長293nmを観察した。そして、化学式4の化合物をCHCl3に10mMの濃度に薄くして293nmでフォトルミネセンス(PL;photoluminescent)スペクトルを測定して364nmで最大発光を観察した(図2)。この時の色純度は、NTSC色座標計でCIE(x,y):0.2534,0.3029を得た。
中間体(A’)(710mg、2.2mmol)をTHF(10mL)に溶かした後、−78℃でn−へキサンに溶けているn−ブチルリチウム(0.92mL、2.3mmol、2.5equiv.)を一滴ずつ滴下した後、1時間攪拌した。この反応混合物にジクロロジフェニルシラン(上記反応式3では、Ph2SiCl2と記した)(0.205mL、1.0mmol)を付加した後、−78℃で1時間攪拌し、常温で5時間攪拌した。
13CNMR(CDCl3、100MHz)δ(ppm)140.5、139.2、137.9、136.4、133.6、133.1、130.0、128.2、126.3、125.9、123.5、120.3、120.1、109.9
前記化学式5の化合物をCHCl3に0.2mMの濃度に薄くしてUVスペクトルを得、最大吸収波長293nmを観察した。そして、化学式5の化合物をCHCl3に10mMの濃度に薄くして293nmでPLを測定して365nmで最大発光を観察した(図6)。この時の色純度は、NTSC色座標計でCIE(x,y):0.2166,0.1401を得た。
下記反応式4によって化学式6の化合物を合成した。
カルバゾール(1g、6mmol)、1,3,5−トリブロモベンゼン(944mg、6mmol)、CuI(50mg、0.6mmol)、K2CO3(3g、48mmol)、そして18−クラウン−6(30mg、0.24mmol)をDMPU(15mL)に溶かした後、175℃で8時間加熱した。
13CNMR(CDCl3、100MHz)δ(ppm)140.4、140.2、134.4、128.6、126.3、123.9、123.8、120.7、120.5、109.5
化学式6の化合物の合成
中間体(B)(200mg、0.41mmol)をTHF(3mL)に溶かした後、−78℃でノルマルへキサン(n−へキサン)に溶けているノルマルブチルリチウム(n−ブチルリチウム)(0.2mL、0.49mmol、2.5eqiv.)を一滴ずつ滴下した後、1時間攪拌した。この反応混合物にジクロロジメチルシラン(0.02mL、0.16mmol)を付加した後、−78℃で1時間、そして常温で5時間攪拌した。
13CNMR(CDCl3、100MHz)δ(ppm)141.7、140.5、139.3、131.0、126.4、126.2、123.6、120.5、120.4、109.5、−2.5
前記過程による化学式6の化合物をCHCl3に0.2mMの濃度に薄くしてUVスペクトルを得、最大吸収波長292.5nmを観察した。そして、化学式6の化合物をCHCl3に10mMの濃度に薄くして292.5nmでPLを測定し、364nmで最大発光を観察した(図8)。この時の色純度は、NTSC色座標計でCIE(x,y):0.2241,0.1926を得た。
アノードとしては、コーニング社の10Ω/cm2 ITO基板を使用し、前記基板の上部にIDE406(イデミツ社)を真空蒸着してHILを600Åの厚さに形成した。次いで、前記HILの上部に前記IDE320(イデミツ社)を300Åの厚さに真空蒸着してHTLを形成した。前記HTLの上部に90:10混合重量比の化学式4の化合物とTEB002(コビオン社)の混合物とを真空蒸着して300Åの厚さにEMLを形成した。
EML形成時、90:10混合重量比の化学式4の化合物及びTEB002(コビオン社)の混合物の代わりに、80:20混合重量比の化学式4の化合物及びTEB002(コビオン社)の混合物を使用したことを除いては、参考例1と同じ方法で実施して有機電界発光素子を完成した。
EML形成時、90:10混合重量比の化学式4の化合物及びTEB002(コビオン社)の混合物の代わりに、90:10混合重量比の化学式5の化合物及びTEB002(コビオン社)の混合物を使用したことを除いては、参考例1と同じ方法で実施して有機電界発光素子を完成した。
EML形成時、90:10混合重量比の化学式4の化合物及びTEB002(コビオン社)の混合物の代わりに、90:10混合重量比の化学式6の化合物及びTEB002(コビオン社)の混合物を使用したことを除いては、参考例1と同じ方法で実施して有機電界発光素子を完成した。
10 基板、
12 アノード、
14 ホール注入層(HIL)、
16 ホール輸送層(HTL)、
18 発光層(EML)、
20 ホールブロッキング層(HBL)、
22 電子輸送層(ETL)、
24 電子注入層(EIL)、
26 カソード。
Claims (8)
- 下記化学式1で表示されることを特徴とする化合物:
Xは−Si(A1)(A2)−であり、
A1、A2、R1ないしR24は、独立的に水素原子、C1−C30のYで置換されたまたは非置換のアルキル基、C1−C30のYで置換されたまたは非置換のアシル基、C1−C30のYで置換されたまたは非置換のアルコキシカルボニル基、C1−C30のYで置換されたまたは非置換のアルコキシ基、C2−C30のYで置換されたまたは非置換のアルケニル基、C2−C30のYで置換されたまたは非置換のアルキニル基、C2−C30のYで置換されたまたは非置換のアルキルカルボキシル基、C6−C30のYで置換されたまたは非置換のアリール基、C6−C30のYで置換されたまたは非置換のアラルキル基、C6−C30のYで置換されたまたは非置換のアラルキルオキシ基、C2−C30のYで置換されたまたは非置換のヘテロアリール基、C2−C30のYで置換されたまたは非置換のヘテロアリールオキシ基、C6−C30のYで置換されたまたは非置換のアリールオキシ基、C6−C30のYで置換されたまたは非置換のアリールオキシカルボニル基、C6−C30のYで置換されたまたは非置換のアリールアルケニル基、C6−C30のYで置換されたまたは非置換のアリールアルキニル基、C6−C30のYで置換されたまたは非置換のアリールカルボキシル基、C2−C30のYで置換されたまたは非置換のヘテロアラルキル基、C4ないしC30のYで置換されたまたは非置換のシクロアルキル基、−N(R)(R’)(但し、RとR’とは相互独立的に水素原子、C1−C30のアルキル基、C6−C30のアリール基またはC2−C30のヘテロアリール基である)、シアノ基、ヒドロキシル基、カルボキシル基であり、
Yはハロゲン原子、ヒドロキシル基、ニトロ基、シアノ基、アミノ基、アミジノ基、ヒドラジノ基(−HN−NH 2 )、ヒドラゾノ基(=N−NH 2 )、カルボキシル基もしくはその塩、スルホン酸基もしくはその塩、リン酸基もしくはその塩、またはC1−C30のアルキル基、C1−C30のアルケニル基、C1−C30のアルキニル基、C6−C30のアリール基、C7−C20のアリールアルキル基、C2−C20のヘテロアリール基、またはC3−C30のヘテロアリールアルキル基であり、
またはR1ないしR24のうち隣接した2個以上が相互に連結されて環が形成されていてもよい。 - A 1 およびA 2 は、独立的に水素原子、C1−C30のYで置換されたまたは非置換のアルキル基、C1−C30のYで置換されたまたは非置換のアシル基、C1−C30のYで置換されたまたは非置換のアルコキシカルボニル基、C1−C30のYで置換されたまたは非置換のアルコキシ基、C2−C30のYで置換されたまたは非置換のアルケニル基、C2−C30のYで置換されたまたは非置換のアルキニル基、C2−C30のYで置換されたまたは非置換のアルキルカルボキシル基、フェニル基、ビフェニル基、もしくはナフチル基、C6−C30のYで置換されたまたは非置換のアラルキル基、C6−C30のYで置換されたまたは非置換のアラルキルオキシ基、C2−C30のYで置換されたまたは非置換のヘテロアリール基、C2−C30のYで置換されたまたは非置換のヘテロアリールオキシ基、C6−C30のYで置換されたまたは非置換のアリールオキシ基、C6−C30のYで置換されたまたは非置換のアリールオキシカルボニル基、C6−C30のYで置換されたまたは非置換のアリールアルケニル基、C6−C30のYで置換されたまたは非置換のアリールアルキニル基、C6−C30のYで置換されたまたは非置換のアリールカルボキシル基、C2−C30のYで置換されたまたは非置換のヘテロアラルキル基、C4ないしC30のYで置換されたまたは非置換のシクロアルキル基、−N(R)(R’)(但し、RとR’とは相互独立的に水素原子、C1−C30のアルキル基、C6−C30のアリール基またはC2−C30のヘテロアリール基である)、シアノ基、ヒドロキシル基、カルボキシル基であり、
Yはハロゲン原子、ヒドロキシル基、ニトロ基、シアノ基、アミノ基、アミジノ基、ヒドラジノ基(−HN−NH 2 )、ヒドラゾノ基(=N−NH 2 )、カルボキシル基もしくはその塩、スルホン酸基もしくはその塩、リン酸基もしくはその塩、またはC1−C30のアルキル基、C1−C30のアルケニル基、C1−C30のアルキニル基、C6−C30のアリール基、C7−C20のアリールアルキル基、C2−C20のヘテロアリール基、またはC3−C30のヘテロアリールアルキル基であることを特徴とする請求項1に記載の化合物。 - 一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1〜4のいずれか1項に記載の化合物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。
- 前記発光層が可視領域のりん光または蛍光ドーパントをさらに含むことを特徴とする請求項6に記載の有機電界発光素子。
- 前記有機膜が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5に記載の有機電界発光素子。
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