JP5536618B2 - 有機電界発光装置 - Google Patents
有機電界発光装置 Download PDFInfo
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- JP5536618B2 JP5536618B2 JP2010254990A JP2010254990A JP5536618B2 JP 5536618 B2 JP5536618 B2 JP 5536618B2 JP 2010254990 A JP2010254990 A JP 2010254990A JP 2010254990 A JP2010254990 A JP 2010254990A JP 5536618 B2 JP5536618 B2 JP 5536618B2
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- electroluminescent device
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- 238000005401 electroluminescence Methods 0.000 title description 7
- 239000010410 layer Substances 0.000 claims description 89
- -1 triarylamine compound Chemical class 0.000 claims description 38
- 230000005525 hole transport Effects 0.000 claims description 33
- 239000012044 organic layer Substances 0.000 claims description 27
- 150000001412 amines Chemical class 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 20
- 150000003216 pyrazines Chemical class 0.000 claims description 19
- 125000006617 triphenylamine group Chemical group 0.000 claims description 14
- 150000001454 anthracenes Chemical class 0.000 claims description 13
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 12
- 125000005504 styryl group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 6
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000005265 dialkylamine group Chemical group 0.000 claims description 3
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000002347 injection Methods 0.000 description 25
- 239000007924 injection Substances 0.000 description 25
- 229920002554 vinyl polymer Polymers 0.000 description 19
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 15
- 239000000758 substrate Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 12
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 235000010290 biphenyl Nutrition 0.000 description 9
- 239000004305 biphenyl Substances 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 6
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 125000001725 pyrenyl group Chemical group 0.000 description 6
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- ZVQPLPSCABMKLZ-UHFFFAOYSA-N 3-methyl-9-[4-[4-(3-methylcarbazol-9-yl)phenyl]phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC(C)=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=C(C)C=C3C3=CC=CC=C32)C=C1 ZVQPLPSCABMKLZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229920000767 polyaniline Polymers 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 125000005956 isoquinolyl group Chemical group 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- QZXNDEONRUSYFB-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]-3-methylaniline Chemical compound CC1=CC=CC(NC=2C=CC(=CC=2)C=2C=CC(N)=CC=2)=C1 QZXNDEONRUSYFB-UHFFFAOYSA-N 0.000 description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000002098 pyridazinyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 125000005493 quinolyl group Chemical group 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- YMRHXVOHLPIMNN-UHFFFAOYSA-N 1-n-(3-methylphenyl)-2-n,2-n-diphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 YMRHXVOHLPIMNN-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
- 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 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
- MVIXNQZIMMIGEL-UHFFFAOYSA-N 4-methyl-n-[4-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 MVIXNQZIMMIGEL-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
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 2
- 241000796522 Olene Species 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 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
- 239000011368 organic material Substances 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003220 pyrenes Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 2
- 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 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- TWELBQMSBSLKDQ-UHFFFAOYSA-N 9-n,10-n-bis(4-butylphenyl)-9-n,10-n-bis(2-methylphenyl)phenanthrene-9,10-diamine Chemical compound C1=CC(CCCC)=CC=C1N(C=1C2=CC=CC=C2C2=CC=CC=C2C=1N(C=1C=CC(CCCC)=CC=1)C=1C(=CC=CC=1)C)C1=CC=CC=C1C TWELBQMSBSLKDQ-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- SOFASJSIZMFTJM-UHFFFAOYSA-N CC(C)(c1c2)c(cc(cc3)N(c(cc4)ccc4F)c(cc4)ccc4F)c3-c1cc(C(C)(C)c1c3)c2-c1ccc3N(c(cc1)ccc1F)c(cc1)ccc1F Chemical compound CC(C)(c1c2)c(cc(cc3)N(c(cc4)ccc4F)c(cc4)ccc4F)c3-c1cc(C(C)(C)c1c3)c2-c1ccc3N(c(cc1)ccc1F)c(cc1)ccc1F SOFASJSIZMFTJM-UHFFFAOYSA-N 0.000 description 1
- AALWAAHLDVBICG-UHFFFAOYSA-N CC1=C(C=CC=C1)N(C=1C2=CC=CC=C2C=2C=CC=CC2C1N(C1=CC=C(C=C1)CCCC)C1=C(C=CC=C1)C)C1=CC=C(C=C1)CCCC.C1(=CC=CC=C1)N(C1=CC=C(C=C1)C1=CC=C(C=C1)N(C1=CC=CC2=CC=CC=C12)C1=CC=CC=C1)C1=CC=CC2=CC=CC=C12 Chemical compound CC1=C(C=CC=C1)N(C=1C2=CC=CC=C2C=2C=CC=CC2C1N(C1=CC=C(C=C1)CCCC)C1=C(C=CC=C1)C)C1=CC=C(C=C1)CCCC.C1(=CC=CC=C1)N(C1=CC=C(C=C1)C1=CC=C(C=C1)N(C1=CC=CC2=CC=CC=C12)C1=CC=CC=C1)C1=CC=CC2=CC=CC=C12 AALWAAHLDVBICG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 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
- 241001024304 Mino Species 0.000 description 1
- AWFDUOVDQHJMKG-UHFFFAOYSA-N N-(3-methylphenyl)-2-phenoxyaniline Chemical compound CC=1C=C(C=CC=1)NC1=C(C=CC=C1)OC1=CC=CC=C1 AWFDUOVDQHJMKG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 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
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 150000001492 aromatic hydrocarbon derivatives Chemical class 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 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
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 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
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical class O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 125000005843 halogen group Chemical group 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 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
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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
- 229920003023 plastic Polymers 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 230000009666 qualitative growth Effects 0.000 description 1
- 230000009663 quantitative growth Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- LGYQERJJBDQQHH-UHFFFAOYSA-N spiro[adamantane-2,9'-fluorene] Chemical class C1C2CC3CC1CC(C2)C31c2ccccc2-c2ccccc12 LGYQERJJBDQQHH-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002207 thermal evaporation Methods 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
- 239000012780 transparent material Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
-
- 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
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Description
第1電極と第2電極との間に、少なくとも1個以上の青色発光層を使用する有機電界発光素子において、ピラジン誘導体をフルオレン・モイエティを含有するトリフェニルアミン化合物にドーピングし、有機電界発光素子の特性を評価した。ドーピング濃度は0〜100%まで、ドーピング厚は0〜2100Åまで評価したが、そのうち顕著に特性が向上する条件を実施例として示した。ただし、素子の製作時に蒸着される有機膜の厚さは、クリスタル・センサ(crystal sensor)でモニタリングした。
・・・(化合物2)
・・・(化合物3)
前記第1電極がパターニングされている基板上部に、まず4,4’−ビス(3−メチル−9−カルバゾリル)−1,1’−ビフェニルに、ヘキサアザトリフェニレンヘキサカルボキシルニトリルを質量比97:3で同時蒸着し、100Å厚に真空蒸着した混合有機層を形成し、N,N’−ジフェニル−N,N’−(3−メチルフェニル)−1,1−ビフェニル−4,4’−ジアミンを1300Å厚に真空蒸着し、正孔輸送層を形成した。
前記第1電極がパターニングされている基板上部に、まず化合物4のトリフェニルアミン誘導体に、ヘキサアザトリフェニレンヘキサカルボキシルニトリルを、質量比97:3で同時蒸着し、100Å厚に真空蒸着して混合有機層を形成し、化合物4のトリフェニルアミン誘導体を1300Å厚に真空蒸着し、正孔輸送層を形成したことを除き、実施例1と同じ方法によって、有機電界発光装置を製作した。
前記第1電極がパターニングされている基板上部に、混合有機層は形成せずに、4,4’−ビス(3−メチル−9−カルバゾリル)−1,1’−ビフェニルを1400Å厚に真空蒸着し、正孔輸送層を形成したことを除き、実施例1と同じ方法によって、有機電界発光装置を製作した。
前記第1電極がパターニングされている基板上部に、混合有機層は形成せずに、化合物4のトリフェニルアミン誘導体を1400Å厚に真空蒸着し、正孔輸送層を形成したことを除き、実施例1と同じ方法によって、有機電界発光装置を製作した。
前記第1電極がパターニングされている基板上部に、まずα−N,N’−ジ(1−ナフチル)−N,N’−ジフェニルベンジジン(NPB)に、ヘキサアザトリフェニレンヘキサカルボキシルニトリルを質量比97:3で同時蒸着し、100Å厚に真空蒸着した混合有機層を形成し、α−NPBを1300Å厚に真空蒸着し、正孔輸送層を形成したことを除き、実施例1と同じ方法によって、有機電界発光装置を製作した。
前記実施例1〜3及び比較例1〜3で製作した有機電界発光装置の効率と駆動電圧とを、PR650輝度計と、KEITHLEYの238 HIGH CURRENT SOURCE MEASURE UNITで評価した。このとき、有機電界発光素子に印加された電圧は、DC2.0Vから0.5V間隔で5Vまで同一素子構造に対して、それぞれ異なる8個以上のデータを収集して評価した。結果を下記表1に示した。
Claims (10)
- 第1電極、第2電極、前記第1電極及び前記第2電極間に介在された発光層、並びに、前記第1電極及び前記発光層間に介在された混合有機層を含み、
前記混合有機層は、カルバゾール・モイエティ又はフルオレン・モイエティの少なくとも何れか一方を含有するトリフェニルアミン誘導体と、ピラジン誘導体と、を含み、
前記発光層は、アントラセン誘導体、アミン含有スチリル誘導体又はこれらの混合物を含み、
前記アントラセン誘導体は、下記構造式11〜構造式19で表される化合物からなる群より選択され、
・・・(構造式11)
・・・(構造式12)
・・・(構造式13)
・・・(構造式14)
・・・(構造式15)
・・・(構造式16)
・・・(構造式17)
・・・(構造式18)
・・・(構造式19)
前記アミン含有スチリル誘導体は、下記構造式20〜構造式24で表される化合物からなる群より選択されることを特徴とする、有機電界発光装置。
・・・(構造式20)
・・・(構造式21)
・・・(構造式22)
・・・(構造式23)
・・・(構造式24) - 前記ピラジン誘導体は、ヘキサアザトリフェニレン誘導体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装置。
- 前記ピラジン誘導体は、下記の構造式で表されることを特徴とする、請求項1に記載の有機電界発光装置。
ここで、前記構造式において、Rは、同一であるか、またはそれぞれ独立して、水素、C1−C10のアルキル基、アルキルオキシ基、ジアルキルアミン基、ハロゲンまたはシアノ基である。 - 正孔輸送層をさらに含むことを特徴とする、請求項1に記載の有機電界発光装置。
- 前記混合有機層は、前記正孔輸送層と第1電極との間に形成されたことを特徴とする、請求項4に記載の有機電界発光装置。
- 前記正孔輸送層は、トリアリールアミン系化合物であることを特徴とする、請求項4に記載の有機電界発光装置。
- 前記混合有機層の厚さは、2〜210nmであることを特徴とする、請求項1〜6のいずれか1項に記載の有機電界発光装置。
- 前記ピラジン誘導体の含有量は、前記混合有機層100質量部に対して、0.1〜95質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装置。
- 前記正孔輸送層の厚さは、3〜180nmであることを特徴とする、請求項4に記載の有機電界発光装置。
- リチウムキノレート及び有機物を含む混合電子輸送層をさらに含むことを特徴とする、請求項1〜9のいずれか1項に記載の有機電界発光装置。
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KR1020090109703A KR101137388B1 (ko) | 2009-11-13 | 2009-11-13 | 유기 전계 발광 장치 |
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EP1860097B1 (en) * | 2005-03-18 | 2011-08-10 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and organic electroluminescence device utilizing the same |
KR101511169B1 (ko) * | 2012-02-07 | 2015-04-13 | 삼성디스플레이 주식회사 | 아민계 화합물 및 이를 포함한 유기 발광 소자 |
US9882143B2 (en) | 2012-02-07 | 2018-01-30 | Samsung Display Co., Ltd. | Amine-based compound and organic light-emitting diode including the same |
US9181474B2 (en) * | 2012-02-07 | 2015-11-10 | Samsung Display Co., Ltd. | Amine-based compound and organic light-emitting diode including the same |
KR20140122613A (ko) | 2013-04-10 | 2014-10-20 | 삼성디스플레이 주식회사 | 헤테로아릴계 화합물 및 이를 포함한 유기 발광 소자 |
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JP6600495B2 (ja) | 2015-06-17 | 2019-10-30 | 三星ディスプレイ株式會社 | 有機電界発光素子用材料及びこれを用いた有機電界発光素子 |
KR102560940B1 (ko) | 2015-06-17 | 2023-08-01 | 삼성디스플레이 주식회사 | 모노 아민 유도체 및 이를 포함하는 유기 전계 발광 소자 |
JP7325731B2 (ja) | 2018-08-23 | 2023-08-15 | 国立大学法人九州大学 | 有機エレクトロルミネッセンス素子 |
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