JP4571057B2 - 有機電界発光素子 - Google Patents
有機電界発光素子 Download PDFInfo
- Publication number
- JP4571057B2 JP4571057B2 JP2005306313A JP2005306313A JP4571057B2 JP 4571057 B2 JP4571057 B2 JP 4571057B2 JP 2005306313 A JP2005306313 A JP 2005306313A JP 2005306313 A JP2005306313 A JP 2005306313A JP 4571057 B2 JP4571057 B2 JP 4571057B2
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- Prior art keywords
- light emitting
- iridium
- emitting layer
- layer
- group
- Prior art date
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- 238000005401 electroluminescence Methods 0.000 title claims description 8
- 239000000463 material Substances 0.000 claims description 31
- 239000000126 substance Substances 0.000 claims description 29
- 238000002347 injection Methods 0.000 claims description 23
- 239000007924 injection Substances 0.000 claims description 23
- 230000005525 hole transport Effects 0.000 claims description 21
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000002019 doping agent Substances 0.000 claims description 14
- 229910052741 iridium Inorganic materials 0.000 claims description 12
- 230000000903 blocking effect Effects 0.000 claims description 11
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 8
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000007983 Tris buffer Substances 0.000 claims description 7
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 6
- -1 bis (hydroxyquinoline) aluminum group Chemical group 0.000 claims description 6
- 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 claims description 6
- XSNBULILWHLFQU-UHFFFAOYSA-N 2,3-dithiophen-2-ylpyridine Chemical group C1=CSC(C=2C(=NC=CC=2)C=2SC=CC=2)=C1 XSNBULILWHLFQU-UHFFFAOYSA-N 0.000 claims description 2
- NRSBAUDUBWMTGL-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)pyridine Chemical compound S1C2=CC=CC=C2C=C1C1=CC=CC=N1 NRSBAUDUBWMTGL-UHFFFAOYSA-N 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
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- SHNBXKOUKNSCSQ-UHFFFAOYSA-N iridium;1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 SHNBXKOUKNSCSQ-UHFFFAOYSA-N 0.000 claims description 2
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 claims 1
- XBHOUXSGHYZCNH-UHFFFAOYSA-N 2-phenyl-1,3-benzothiazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2S1 XBHOUXSGHYZCNH-UHFFFAOYSA-N 0.000 claims 1
- 239000000758 substrate Substances 0.000 description 9
- 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 8
- 238000000034 method Methods 0.000 description 8
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 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 3
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- 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
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- MBPCKEZNJVJYTC-UHFFFAOYSA-N 4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 MBPCKEZNJVJYTC-UHFFFAOYSA-N 0.000 description 2
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- 239000010405 anode material Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
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- 238000004506 ultrasonic cleaning Methods 0.000 description 2
- QCVAALUUJVLCTR-UHFFFAOYSA-N 1,1'-biphenyl 9H-carbazol-1-ol Chemical group C1=CC=CC=C1C1=CC=CC=C1.N1C2=CC=CC=C2C2=C1C(O)=CC=C2 QCVAALUUJVLCTR-UHFFFAOYSA-N 0.000 description 1
- MNHSTWRXCNIKFM-UHFFFAOYSA-N 1,2-diethyl-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(CC)C(CC)=C3CC2=C1 MNHSTWRXCNIKFM-UHFFFAOYSA-N 0.000 description 1
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- QTPLEVOKSWEYAC-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene Chemical compound C=1C=CC=CC=1C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC=CC=C1 QTPLEVOKSWEYAC-UHFFFAOYSA-N 0.000 description 1
- WECOUKMONWFOGF-UHFFFAOYSA-N 1-[2-[3,5-bis[2-(9h-carbazol-1-yl)-5-methoxyphenyl]phenyl]-4-methoxyphenyl]-9h-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C1=CC=C(OC)C=C1C1=CC(C=2C(=CC=C(OC)C=2)C=2C=3NC4=CC=CC=C4C=3C=CC=2)=CC(C=2C(=CC=C(OC)C=2)C=2C=3NC4=CC=CC=C4C=3C=CC=2)=C1 WECOUKMONWFOGF-UHFFFAOYSA-N 0.000 description 1
- AHBDIQVWSLNELJ-UHFFFAOYSA-N 1-[3,5-bis(9h-carbazol-1-yl)phenyl]-9h-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C1=CC(C=2C=3NC4=CC=CC=C4C=3C=CC=2)=CC(C2=C3NC=4C(C3=CC=C2)=CC=CC=4)=C1 AHBDIQVWSLNELJ-UHFFFAOYSA-N 0.000 description 1
- DBDOZRBRAYSLFX-UHFFFAOYSA-N 1-[4-[4-(9h-carbazol-1-yl)-2-methylphenyl]-3-methylphenyl]-9h-carbazole Chemical group N1C2=CC=CC=C2C2=C1C(C=1C=C(C(=CC=1)C=1C(=CC(=CC=1)C=1C3=C(C4=CC=CC=C4N3)C=CC=1)C)C)=CC=C2 DBDOZRBRAYSLFX-UHFFFAOYSA-N 0.000 description 1
- IERDDDBDINUYCD-UHFFFAOYSA-N 1-[4-[4-(9h-carbazol-1-yl)phenyl]phenyl]-9h-carbazole Chemical group C12=CC=CC=C2NC2=C1C=CC=C2C(C=C1)=CC=C1C(C=C1)=CC=C1C1=C2NC3=CC=CC=C3C2=CC=C1 IERDDDBDINUYCD-UHFFFAOYSA-N 0.000 description 1
- BEHYHCBDZZQSBV-UHFFFAOYSA-N 2,3-dimethyl-1,10-phenanthroline Chemical compound C1=CC=NC2=C(N=C(C(C)=C3)C)C3=CC=C21 BEHYHCBDZZQSBV-UHFFFAOYSA-N 0.000 description 1
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- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
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- YGXMMMPUTDCEAF-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis-phenyl-1,3,5-triazine-2,4,6-triamine Chemical compound C1=CC=CC=C1N(C=1N=C(N=C(N=1)N(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 YGXMMMPUTDCEAF-UHFFFAOYSA-N 0.000 description 1
- CZHQZVUBGSXJFF-UHFFFAOYSA-N 2-n,4-n,6-n-trinaphthalen-1-yl-2-n,4-n,6-n-triphenyl-1,3,5-triazine-2,4,6-triamine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=NC(N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)=NC(N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)=N1 CZHQZVUBGSXJFF-UHFFFAOYSA-N 0.000 description 1
- CDBMGJUEACTJIC-UHFFFAOYSA-N 2-n,4-n,6-n-trinaphthalen-2-yl-2-n,4-n,6-n-triphenyl-1,3,5-triazine-2,4,6-triamine Chemical compound C1=CC=CC=C1N(C=1N=C(N=C(N=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=CC=C2)C2=C1 CDBMGJUEACTJIC-UHFFFAOYSA-N 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
- FJXNABNMUQXOHX-UHFFFAOYSA-N 4-(9h-carbazol-1-yl)-n,n-bis[4-(9h-carbazol-1-yl)phenyl]aniline Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C(C=C1)=CC=C1N(C=1C=CC(=CC=1)C=1C=2NC3=CC=CC=C3C=2C=CC=1)C(C=C1)=CC=C1C1=C2NC3=CC=CC=C3C2=CC=C1 FJXNABNMUQXOHX-UHFFFAOYSA-N 0.000 description 1
- 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 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
- YUXBNNVWBUTOQZ-UHFFFAOYSA-N 4-phenyltriazine Chemical compound C1=CC=CC=C1C1=CC=NN=N1 YUXBNNVWBUTOQZ-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- YAPIJPOCONTNDY-UHFFFAOYSA-N N1C2=CC=CC=C2C2=C1C(C1=CC=C(C=C1)[SiH2]C=1C=CC(=CC=1)C=1C3=C(C4=CC=CC=C4N3)C=CC=1)=CC=C2 Chemical compound N1C2=CC=CC=C2C2=C1C(C1=CC=C(C=C1)[SiH2]C=1C=CC(=CC=1)C=1C3=C(C4=CC=CC=C4N3)C=CC=1)=CC=C2 YAPIJPOCONTNDY-UHFFFAOYSA-N 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 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
- 150000001716 carbazoles Chemical class 0.000 description 1
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- 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
- 230000007423 decrease Effects 0.000 description 1
- 125000004986 diarylamino group Chemical group 0.000 description 1
- 238000001035 drying Methods 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
- 230000006872 improvement Effects 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
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 1
- IVPZJRKMZLRFIL-UHFFFAOYSA-N iridium;pyridine Chemical compound [Ir].C1=CC=NC=C1 IVPZJRKMZLRFIL-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 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
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
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- 230000008569 process Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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Description
しかし、これまで知られているカルバゾール系化合物を利用する場合、燐光デバイスの効率及び寿命特性が満足するほどのレベルに至らずに改善の余地が多い。
A−C−B (1)
[前記化学式で、Aは正孔輸送単位であり、Bは電子輸送単位であり、Cは結合であるか、または連結基である。]
図1Aの有機発光表示素子は、第1電極の上部に正孔輸送層と発光層とが順次に積層されており、前記発光層の上部に電子輸送層と第2電極とが順次に積層されている構造を有する。図1Bの有機発光表示素子は、図1Aの有機発光表示素子で、第1電極と正孔輸送層との間に正孔注入層がさらに積層され、電子輸送層と第2電極との間に電子注入層がさらに積層されている構造を有する。図1Cの有機発光表示素子は、図1Bの有機発光表示素子で、発光層と電子輸送層との間に正孔阻止層がさらに積層されている構造を有する。
前記カソード金属としては、リチウム(Li)、マグネシウム(Mg)、アルミニウム(Al)、アルミニウム−リチウム(Al−Li)、カルシウム(Ca)、マグネシウム−インジウム(Mg−In)、マグネシウム−銀(Mg−Ag)などが利用される。
2−メチル−8−キノリノール(0.01mole)をエタノールと水との混合溶液で再結晶させた後、再結晶した物質をアルミニウムイソプロポキシド(0.005mole)と無水エチルエーテル中で撹拌する。30分の反応後に溶液を濾過した後、ヒドロキシカルバゾールビフェニル(0.01mole)をエチルエーテル溶液に入れて加熱し、6時間反応させた後で冷却する。固体物質を得た後で洗浄と乾燥とを行って本化合物を製造する。
アノードは、ITOガラス基板(15Ω/cm2、1,200Å;コーニング社製)を50mmx50mmx0.7mmサイズに裁断し、イソプロピルアルコールと純水の中でそれぞれ5分間超音波洗浄した後、30分間紫外線(UV)、オゾン洗浄して使用した。
前記基板上部にN,N’−ジ(1−ナフチル)−N,N’−ジフェニルベンジジン(NPD)を真空蒸着し、正孔輸送層を600Åの厚さに形成した。
前記正孔輸送層の上部に、燐光ホストとして製造した前記双極化合物90重量部と、燐光ドーパントであるトリス(2−フェニルピリジン)イリジウム10重量部とを真空蒸着し、約400Åの厚さに発光層を形成した。
前記発光層の上部に電子輸送物質であるAlq3を蒸着し、約300Å厚さの電子輸送層を形成した。
前記電子輸送層の上部に、LiF 10Å(電子注入層)と、Al 1,000Å(カソード)とを順次に真空蒸着してLiF/Al電極を形成し、図1に図示したような有機電界発光素子を製造した。
アノードは、ITOガラス基板(15Ω/cm2、1,200Å;コーニング社製)を50mmx50mmx0.7mmサイズに裁断し、イソプロピルアルコールと純水の中でそれぞれ5分間超音波洗浄した後、30分間UV、オゾン洗浄して使用した。
前記基板上部にNPDを真空蒸着して正孔輸送層を600Å厚さに形成した。前記正孔輸送層の上部に燐光ホストであるCBPに燐光ドーパントであるトリス(2−フェニルピリジン)イリジウム10重量部を真空蒸着し、約400Åの厚さに発光層を形成した。
前記発光層の上部に電子輸送物質であるAlq3を蒸着して約300Å厚さの電子輸送層を形成した。
前記電子輸送層の上部にLiF 10Å(電子注入層)とAl 1,000Å(カソード)とを順次に真空蒸着してLiF/Al電極を形成し、図1に図示したような有機電界発光素子を製造した。
前記実施例1及び比較例1によって製造された有機電界発光素子において、効率及び寿命特性を調べた。
また、寿命特性は、最初の発光輝度が50%レベルまで減少する時間で表すが、実施例1の有機電界発光素子は、1,000cd/m2で7,000時間であり、比較例1の有機電界発光素子は、1,000cd/m2で5,000時間と示され、実施例1は、比較例1の場合に比べて寿命特性が改善されていることが確認された。
Claims (6)
- 第1電極及び第2電極間に燐光ドーパントを含む発光層を有する有機電界発光素子において、
前記発光層は、燐光ホストとして下記化学式1を有する双極化合物を含むことを特徴とする有機電界発光素子:
A−C−B (1)
[前記化学式1で、Aは正孔輸送単位であり、Bは電子輸送単位であり、Cは結合である。]
であって、
前記正孔輸送単位Aは、下記の化学式:
で表され、
前記電子輸送単位Bが、ビス(ヒドロキシキノリン)アルミニウム基またはビス(2−メチルヒドロキシキノリン)アルミニウム基である、有機電界発光素子。 - 前記発光層で燐光ホストである双極化合物の含有量は、発光層の形成材料の総重量100重量部を基準として70から99重量部であることを特徴とする請求項1に記載の有機電界発光素子。
- 前記発光層で燐光ドーパントが、
ビスチエニルピリジンアセチルアセトネートイリジウム、ビス(ベンゾチエニルピリジン)アセチルアセトネートイリジウム、ビス(2−フェニルベンゾチアゾール)アセチルアセトネートイリジウム、ビス(1−フェニルイソキノリン)イリジウムアセチルアセトネート、トリス(1−フェニルイソキノリン)イリジウム、トリス(フェニルピリジン)イリジウム、トリス(2−ビフェニルピリジン)イリジウム、トリス(3−ビフェニルピリジン)イリジウム、及びトリス(4−ビフェニルピリジン)イリジウムからなる群から選択された一つ以上であることを特徴とする請求項1に記載の有機電界発光素子。 - 前記第1電極と発光層との間に正孔注入層及び正孔輸送層のうちから選択された一つ以上がさらに備わることを特徴とする請求項1に記載の有機電界発光素子。
- 前記発光層と第2電極との間に正孔阻止層、電子輸送層及び電子注入層のうちから選択された一つ以上がさらに備わることを特徴とする請求項1に記載の有機電界発光素子。
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