JP4683882B2 - ピラン誘導体とその製造方法、並びにピラン誘導体を用いた発光素子及び発光装置。 - Google Patents
ピラン誘導体とその製造方法、並びにピラン誘導体を用いた発光素子及び発光装置。 Download PDFInfo
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- JP4683882B2 JP4683882B2 JP2004246178A JP2004246178A JP4683882B2 JP 4683882 B2 JP4683882 B2 JP 4683882B2 JP 2004246178 A JP2004246178 A JP 2004246178A JP 2004246178 A JP2004246178 A JP 2004246178A JP 4683882 B2 JP4683882 B2 JP 4683882B2
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- light
- formula
- pyran
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- emitting element
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- 150000004880 oxines Chemical class 0.000 title claims description 64
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical class C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 title description 3
- 125000005504 styryl group Chemical group 0.000 claims description 32
- POXIZPBFFUKMEQ-UHFFFAOYSA-N 2-cyanoethenylideneazanide Chemical group [N-]=C=[C+]C#N POXIZPBFFUKMEQ-UHFFFAOYSA-N 0.000 claims description 28
- 239000000758 substrate Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000005264 aryl amine group Chemical group 0.000 claims description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004986 diarylamino 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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
- DZFWNZJKBJOGFQ-UHFFFAOYSA-N julolidine Chemical group C1CCC2=CC=CC3=C2N1CCC3 DZFWNZJKBJOGFQ-UHFFFAOYSA-N 0.000 claims description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 2
- 239000011159 matrix material Substances 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 82
- 239000000463 material Substances 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000010408 film Substances 0.000 description 24
- -1 aryl aldehyde compound Chemical class 0.000 description 22
- 239000000126 substance Substances 0.000 description 21
- 239000007787 solid Substances 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 18
- 238000002347 injection Methods 0.000 description 16
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000000295 emission spectrum Methods 0.000 description 14
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- 238000000034 method Methods 0.000 description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
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- 150000003973 alkyl amines Chemical group 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 8
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group 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 8
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- RCAFEQWFDGXVLJ-UHFFFAOYSA-N 2-(2-methylpyran-4-ylidene)propanedinitrile Chemical class CC1=CC(=C(C#N)C#N)C=CO1 RCAFEQWFDGXVLJ-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 239000012212 insulator Substances 0.000 description 6
- UESSERYYFWCTBU-UHFFFAOYSA-N 4-(n-phenylanilino)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UESSERYYFWCTBU-UHFFFAOYSA-N 0.000 description 5
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- 0 Cc(cc1)ccc1N(*)[Al] Chemical compound Cc(cc1)ccc1N(*)[Al] 0.000 description 4
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- 125000004947 alkyl aryl amino group Chemical group 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
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- 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 4
- 229920003023 plastic Polymers 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000004544 sputter deposition Methods 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- KWDDGUCSVPNQBN-UHFFFAOYSA-N C#CC1=CCC=CO1 Chemical compound C#CC1=CCC=CO1 KWDDGUCSVPNQBN-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000000565 sealant Substances 0.000 description 3
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- 229910052709 silver Inorganic materials 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 3
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 2
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 2
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 2
- MRUWJENAYHTDQG-UHFFFAOYSA-N 4H-pyran Chemical compound C1C=COC=C1 MRUWJENAYHTDQG-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
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- MNFZZNNFORDXSV-UHFFFAOYSA-N 4-(diethylamino)benzaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C=C1 MNFZZNNFORDXSV-UHFFFAOYSA-N 0.000 description 1
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- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical group C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 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
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 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
- 238000011161 development Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000008020 evaporation 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
- 238000005286 illumination Methods 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method 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
- 239000011787 zinc oxide Substances 0.000 description 1
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
- QEPMORHSGFRDLW-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzoxazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1 QEPMORHSGFRDLW-UHFFFAOYSA-L 0.000 description 1
Images
Landscapes
- Electroluminescent Light Sources (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
本形態では、本発明のピラン誘導体を用いた発光素子の態様について図1を用いて説明する。
−フェニル−アミノ]−ビフェニル(略称:TPD)の他、その誘導体である4,4’−ビス[N−(1−ナフチル)−N−フェニル−アミノ]−ビフェニル(略称
:α−NPD)、あるいは4,4’,4’’−トリス(N,N−ジフェニル−アミ
ノ)−トリフェニルアミン(略称:TDATA)、4,4’,4’’−トリス[N
−(3−メチルフェニル)−N−フェニル−アミノ]−トリフェニルアミン(略称:MTDATA)などのスターバースト型芳香族アミン化合物が挙げられる。
,2”−(1,3,5−ベンゼントリ−イル)−トリス[1−フェニル−1H−ベンズイミダゾール](略称:TPBI)、9,10−ジ(2−ナフチル)アントラセン(略称:DNA)などの公知の化合物を用いることができる。
本形態では、上記一般式(6)で表される本発明のピラン誘導体の製造方法の態様について説明する。
構造式(18)で表される4−(ジシアノメチレン)−2−{p−(ジメチルアミノ)スチリル}−6−{p−(ジフェニルアミノ)スチリル}−4H−ピランの合成方法について説明する。
この化合物の1H−NMRは次のようであった。
1H−NMR(300MHz, CDCl3) d ppm: 7.47−7.40(m, 6H), 7.31(t, 4H, J=7.8Hz), 7.17−7.03(m, 8H), 6.72(d, 2H, J=8.7Hz), 6.61−6.55(m, 3H), 6.51(d, 1H, J=15.9Hz), 3.06(s, 6H)
構造式(19)で表される4−(ジシアノメチレン)−2−(9−ジュロリジン−イル)エチニル−6−{p−(ジフェニルアミノ)スチリル}−4H−ピランの合成方法について説明する。
この化合物の1H−NMRは次のようであった。
1H−NMR(300MHz, CDCl3) d ppm: 7.43−7.26(m, 8H), 7.15−7.00(m, 10H), 6.58−6.38(m, 4H), 3.27−3.23(m, 4H), 2.77−2.73(m, 4H), 2.00−1.94(m, 4H)
構造式(20)で表される4−(ジシアノメチレン)−2−(8−メトキシ−1,1,7,7−テトラメチルジュロリジン−イル)エチニル−6−{p−(ジフェニルアミノ)スチリル}−4H−ピランの合成方法について説明する。
この化合物の1H−NMRは次のようであった。
1H−NMR(300MHz, CDCl3) d ppm:7.73(d, 1H, J=16.2Hz), 7.45(d, 1H, J=15.9Hz), 7.38(d, 2H, J=8.7Hz), 7.32−7.27(m, 5H), 7.14−7.07(m, 6H), 7.03(d, 2H, J=9.0Hz), 6.61−6.55(m, 3H), 6.48(d, 1H, J=15.6Hz),3.83(s, 3H), 3.28−3.24(m,2H), 3.20−3.17(m, 2H), 1.74−1.70(m, 4H), 1.41(s, 6H), 1.30(s, 6H)
構造式(21)で表される4−(ジシアノメチレン)−2−{p−(ジメチルアミノ)スチリル}−6−{p−(N−カルバゾリル)スチリル}−4H−ピランの合成方法について説明する。
この化合物の1H−NMRは次のようであった。
1H−NMR(300MHz, CDCl3) d ppm:8.14(d, 2H, J=7.2Hz), 7.80(d, 2H, J=8.7Hz), 7.67(d, 2H, J=8.7Hz), 7.61−7.28(m, 12H), 6.85−6.52(m, 4H), 3.06(s, 6H)
構造式(22)で表される4−(ジシアノメチレン)−2−(9−ジュロリジン−イル)エチニル−6−{p−(N−カルバゾリル)スチリル}−4H−ピランの合成方法について説明する。
この化合物の1H−NMRは次のようであった。
1H−NMR(300MHz, CDCl3) d ppm:8.14(d, 2H, J=7.2Hz), 7.80(d, 2H, J=8.1Hz), 7.66(d, 2H, J=8.7Hz), 7.57(d, 1H, J=16.2Hz), 7.49−7.28(m, 7H), 7.05(s, 2H), 6.81(d, 1H, J=16.2Hz), 6.84−6.39(m, 3H), 3.27−3.23(m, 4H), 2.77−2.73(m, 4H), 2.00−1.94(m, 4H)
本発明の発光素子との比較例として、Bis構造のピラン誘導体のひとつである4−(ジシアノメチレン)−2,6−ビス{p−(ジメチルアミノ)スチリル}−4H−ピラン(BisDCM)を含む発光素子およびその素子特性について説明する。なお、素子構造は実施例2および実施例3と同様である。
11 TFT
12 TFT
13 発光素子
14 第1の電極
15 発光物質を含む層
16 第2の電極
17 配線
100 基板
101 第1の電極
102 発光物質を含む層
103 第2の電極
111 ホール注入層
112 ホール輸送層
113 発光層
114 電子輸送層
401 駆動回路部
402 画素部
403 駆動回路部
404 封止基板
405 シール材
407 空間
408 引き回し配線
409 FPC(フレキシブルプリントサーキット)
410 素子基板
411 スイッチング用TFT
412 電流制御用TFT
413 第1の電極
414 絶縁物
416 発光物質を含む層
417 第2の電極
418 発光素子
423 nチャネル型TFT
424 pチャネル型TFT
5501 筐体
5502 支持台
5503 表示部
5511 本体
5512 表示部
5513 音声入力
5514 操作スイッチ
5515 バッテリー
5516 受像部
5521 本体
5522 筐体
5523 表示部
5524 キーボード
5531 本体
5532 スタイラス
5533 表示部
5534 操作ボタン
5535 外部インターフェイス
5551 本体
5552 表示部(A)
5553 接眼部
5554 操作スイッチ
5555 表示部(B)
5556 バッテリー
5561 本体
5562 音声出力部
5563 音声入力部
5564 表示部
5565 操作スイッチ
5566 アンテナ
Claims (15)
- 下記一般式
下記式で表わされる、4−(ジシアノメチレン)−2−{p−(ジアルキルアミノ)スチリル}−6−メチル−4H-ピランと、アリールアミン骨格を有するp−(ジアリールアミノ)ベンズアルデヒドとを縮合させることを特徴とする製造方法。
- 請求項1乃至請求項4のいずれか一に記載のピラン誘導体を用いた発光素子。
- 一対の電極間に、請求項1乃至請求項4のいずれか一に記載のピラン誘導体を含む層を有することを特徴とする発光素子。
- 請求項1乃至請求項4のいずれか一に記載のピラン誘導体を発光体として用いていることを特徴とする発光素子。
- 請求項6乃至8のいずれか一に記載の発光素子を有することを特徴とする発光装置。
- 請求項6乃至8のいずれか一に記載の発光素子を同一基板上に複数有することを特徴とするアクティブマトリクス型発光装置。
- 請求項9または10に記載の発光装置を表示部に備えたビデオカメラ。
- 請求項9または10に記載の発光装置を表示部に備えたパーソナルコンピュータ。
- 請求項9または10に記載の発光装置を表示部に備えた携帯情報端末。
- 請求項9または10に記載の発光装置を表示部に備えたデジタルビデオカメラ。
- 請求項9または10に記載の発光装置を表示部に備えた携帯電話。
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