JP5911418B2 - 有機発光素子 - Google Patents
有機発光素子 Download PDFInfo
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- JP5911418B2 JP5911418B2 JP2012285619A JP2012285619A JP5911418B2 JP 5911418 B2 JP5911418 B2 JP 5911418B2 JP 2012285619 A JP2012285619 A JP 2012285619A JP 2012285619 A JP2012285619 A JP 2012285619A JP 5911418 B2 JP5911418 B2 JP 5911418B2
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- substituted
- unsubstituted
- benzo
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- -1 naphthalenediyl group Chemical group 0.000 claims description 248
- 150000001875 compounds Chemical class 0.000 claims description 173
- 125000000623 heterocyclic group Chemical group 0.000 claims description 90
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 85
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 239000000463 material Substances 0.000 claims description 69
- 229910052741 iridium Inorganic materials 0.000 claims description 61
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 61
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 43
- 150000002894 organic compounds Chemical class 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 125000001624 naphthyl group Chemical group 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 239000003446 ligand Substances 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000006267 biphenyl group Chemical group 0.000 claims description 23
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 16
- 239000002184 metal Substances 0.000 claims description 16
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 14
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 13
- 125000005605 benzo group Chemical group 0.000 claims description 12
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 claims description 12
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 11
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 10
- 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 claims description 10
- JQXCGCPMGZBMLE-UHFFFAOYSA-N benzo[f]isoquinoline Chemical group N1=CC=C2C3=CC=CC=C3C=CC2=C1 JQXCGCPMGZBMLE-UHFFFAOYSA-N 0.000 claims description 10
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 10
- 125000005561 phenanthryl group Chemical group 0.000 claims description 10
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 claims description 10
- 125000001725 pyrenyl group Chemical group 0.000 claims description 10
- 230000036961 partial effect Effects 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
- 108091008695 photoreceptors Proteins 0.000 claims description 6
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical group C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 3
- 125000006836 terphenylene group Chemical group 0.000 claims description 3
- 230000010365 information processing Effects 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 196
- 230000015572 biosynthetic process Effects 0.000 description 53
- 238000003786 synthesis reaction Methods 0.000 description 53
- 150000002503 iridium Chemical class 0.000 description 31
- 239000000758 substrate Substances 0.000 description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 21
- 230000000903 blocking effect Effects 0.000 description 18
- 238000000034 method Methods 0.000 description 16
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- 230000005525 hole transport Effects 0.000 description 13
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 10
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 10
- 238000006862 quantum yield reaction Methods 0.000 description 9
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000000470 constituent Substances 0.000 description 8
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 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 7
- 230000006866 deterioration Effects 0.000 description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 7
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000006880 cross-coupling reaction Methods 0.000 description 6
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 125000001041 indolyl group Chemical group 0.000 description 6
- 125000005956 isoquinolyl group Chemical group 0.000 description 6
- 125000006606 n-butoxy group Chemical group 0.000 description 6
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 6
- 125000001715 oxadiazolyl group Chemical group 0.000 description 6
- 125000002971 oxazolyl group Chemical group 0.000 description 6
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 6
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 6
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- 125000000168 pyrrolyl group Chemical group 0.000 description 6
- 125000005493 quinolyl group Chemical group 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 238000000859 sublimation Methods 0.000 description 6
- 230000008022 sublimation Effects 0.000 description 6
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 125000001544 thienyl group Chemical group 0.000 description 6
- NBJKWEHXLWUBOS-UHFFFAOYSA-N 14h-phenanthro[9,10-b]chromene Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1CC1=CC=CC=C1O2 NBJKWEHXLWUBOS-UHFFFAOYSA-N 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 5
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 5
- 125000003373 pyrazinyl group Chemical group 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- 0 Cc1c(C)c(*)c(*)c(*)c1C Chemical compound Cc1c(C)c(*)c(*)c(*)c1C 0.000 description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 238000000103 photoluminescence spectrum Methods 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 3
- UWMISBRPSJFHIR-UHFFFAOYSA-N naphtho[2,3-b][1]benzothiole Chemical compound C1=CC=C2C=C3C4=CC=CC=C4SC3=CC2=C1 UWMISBRPSJFHIR-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- SOSIJULCFHJNTI-UHFFFAOYSA-N triphenyleno[2,1-b]thiophene Chemical compound C1=CC=CC2=C3C(C=CS4)=C4C=CC3=C(C=CC=C3)C3=C21 SOSIJULCFHJNTI-UHFFFAOYSA-N 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- YEUHHUCOSQOCIX-UHFFFAOYSA-N Benzo[b]naphtho[2,1-d]thiophene Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1S2 YEUHHUCOSQOCIX-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 150000001716 carbazoles Chemical class 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000553 poly(phenylenevinylene) Chemical class 0.000 description 2
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- 230000000171 quenching effect Effects 0.000 description 2
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- 238000005215 recombination Methods 0.000 description 2
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
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- 238000001771 vacuum deposition Methods 0.000 description 2
- JGPBJHMWFAOODS-UHFFFAOYSA-N 19-chloro-3-thiapentacyclo[11.8.0.02,10.04,9.016,21]henicosa-1(13),2(10),4,6,8,11,14,16(21),17,19-decaene Chemical compound C1=CC=C2SC3=C(C=4C(=CC=C(C=4)Cl)C=C4)C4=CC=C3C2=C1 JGPBJHMWFAOODS-UHFFFAOYSA-N 0.000 description 1
- RNEOFIVNTNLSEH-UHFFFAOYSA-N 2-bromo-1-benzofuran Chemical compound C1=CC=C2OC(Br)=CC2=C1 RNEOFIVNTNLSEH-UHFFFAOYSA-N 0.000 description 1
- WIFMYMXKTAVDSQ-UHFFFAOYSA-N 2-bromo-1-benzothiophene Chemical compound C1=CC=C2SC(Br)=CC2=C1 WIFMYMXKTAVDSQ-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- RSZPXFNGKYIZRV-UHFFFAOYSA-N 3,6-dimethylphenanthren-9-ol Chemical compound C1=C(C)C=C2C3=CC(C)=CC=C3C=C(O)C2=C1 RSZPXFNGKYIZRV-UHFFFAOYSA-N 0.000 description 1
- MBEIUMZROARQFG-UHFFFAOYSA-N 5-bromonaphtho[1,2-b][1]benzothiole Chemical compound S1C2=C3C=CC=C[C]3C(Br)=CC2=C2[C]1C=CC=C2 MBEIUMZROARQFG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- DZKIUEHLEXLYKM-UHFFFAOYSA-N 9-phenanthrol Chemical compound C1=CC=C2C(O)=CC3=CC=CC=C3C2=C1 DZKIUEHLEXLYKM-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- NEUVARHYLWGENO-UHFFFAOYSA-N 9h-xanthen-2-ylboronic acid Chemical compound C1=CC=C2CC3=CC(B(O)O)=CC=C3OC2=C1 NEUVARHYLWGENO-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
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- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
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- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 108091006149 Electron carriers Proteins 0.000 description 1
- 150000000918 Europium Chemical class 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
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Description
前記有機化合物層が、下記一般式[1]に示されるイリジウム錯体と、下記一般式[21]に示されるヘテロ環含有化合物と、を有することを特徴とする。
前記有機化合物層が、下記一般式[1]で示されるイリジウム錯体と、下記一般式[5]で示されるヘテロ環含有化合物と、を有することを特徴とする。
mは、1乃至3の整数を表し、nは、0乃至2の整数を表す。ただしm+nは、3である。
環Aは、ベンゼン環、ナフタレン環、フルオレン環、フェナンスレン環及び9,9−スピロビフルオレン環から選ばれる環状構造を表し、ベンゾ[f]イソキノリン骨格及びIr金属と共有結合している。尚、環Aは、さらに置換基を有してもよい。
Xは、二座配位子を表す。
部分構造IrX n は、下記一般式[2]乃至[4]に示される構造のいずれかである。
Y 1 及びY 2 は、それぞれアルキル基又は置換あるいは無置換の芳香族炭化水素基を表す。
aは、0乃至4の整数を表す。aが2以上の場合、複数のY 1 は同一であっても異なっていてもよい。
bは、0乃至4の整数を表す。ただし環B 2 がベンゼン環である場合、bは、0乃至3の整数である。bが2以上の場合、複数のY 2 は同一であっても異なっていてもよい。
Ar 1 は、置換あるいは無置換の2価の芳香族炭化水素基を表す。
Ar 2 は、置換あるいは無置換の1価の芳香族炭化水素基を表す。
pは、0乃至4の整数を表す。pが2以上の場合、複数のAr 1 は同一であっても異なっていてもよい。〕
本発明の有機発光素子は、互いに対向し合う一対の電極である陽極と陰極と、これら一対の電極の間に配置される有機化合物層とを少なくとも有する発光素子である。そして本発明の有機発光素子は、有機化合物層に、下記一般式[1]に示されるイリジウム錯体と下記一般式[5]に示されるヘテロ環含有化合物とを有する。
(1)陽極/発光層/陰極
(2)陽極/正孔輸送層/発光層/電子輸送層/陰極
(3)陽極/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
(4)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/陰極
(5)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
(6)陽極/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極
次に、本発明の有機発光素子の構成材料の一つであるイリジウム錯体について説明する。本発明の有機発光素子の構成材料の一つであるイリジウム錯体は、下記一般式[1]に示される化合物である。
次に、本発明の有機発光素子に、発光層のホストとして用いられるヘテロ環含有化合物について説明する。本発明の有機発光素子に含まれるヘテロ環含有化合物は、具体的には、下記一般式[5]に示される化合物である。
以上説明したように、本発明の有機発光素子は、有機化合物層(好ましくは、発光層)に、一般式[1]に示されるイリジウム錯体と、一般式[5]に示されるヘテロ環含有化合物と、を共に有している。
(I)発光層内でのキャリアバランスの向上
(II)発光領域(キャリア再結合領域)の拡大
(III)発光層ホスト材料分子の構造安定性向上
以下に、一般式[1]で定義されるイリジウム錯体の具体的な構造式を例示する。
以下に、一般式[5]で定義されるヘテロ環含有化合物の具体的な構造式を例示する。尚、以下に示される具体例のうち、H−126乃至H140、H145、H146、H−201乃至H229、H301乃至H329、H−401乃至H−444、H−501乃至H−518、H−601乃至H−617、H−626乃至H−636、H−639乃至H−642、H−706、及びH−711乃至H−743は、本発明に含まれる。
以上説明したように、本発明の有機発光素子は、有機化合物層(好ましくは、発光層)に、一般式[1]のイリジウム錯体及び一般式[5]のヘテロ環含有化合物が少なくとも含まれている。ただし、本発明では、これら化合物以外にも、必要に応じて従来公知の低分子系及び高分子系の材料を使用することができる。より具体的には正孔注入輸送性材料、発光アシスト材料、あるいは電子注入輸送性材料等を上記イリジウム錯体及び上記ヘテロ環含有化合物と一緒に使用することができる。
本発明の有機発光素子は、表示装置や照明装置の構成部材として用いることができる。他にも、電子写真方式の画像形成装置の露光光源や液晶表示装置のバックライト、白色光源にカラーフィルターを有する発光装置等の用途がある。カラーフィルターは例えば赤、緑、青の3つの色が透過するフィルターが挙げられる。
[合成例1、2](例示化合物Ir−201、Ir−201の合成)
特許文献1及び非特許文献1乃至4等を参考にして、Ir−101及びIr−201を
下記に示す合成スキームにて合成した。
(1)配位子L(ベンゾ[f]イソキノリン誘導体)の合成
(2)配位子Lを有するクロロ架橋錯体(Ir2L4Cl2)の合成
(3)補助配位子Xを有する錯体(IrL2X)の合成(Ir−201の合成、合成例1)
(4)配位子Lが3個配位されている錯体(IrL3)の合成(Ir−101の合成、合成例2)
上記合成例1及び2の合成スキームにおいて、合成原料となる化合物(M1乃至M3)を適宜変更する以外は、合成例1及び2と同様の合成方法により表1に示すイリジウム錯体を合成した。得られたイリジウム錯体について、合成例1及び2で得たイリジウム錯体と同様に同定を行い構造を確認すると共に、PLスペクトル測定により最大発光ピーク波長測定を行った。結果を表1に示す。
特許文献3等を参考にして、下記に示す合成スキームにてIr−515を合成した。
合成例17において、補助配位子(フェニルピリジン)の投入量を適宜調節すること以外は、合成例17と同様の合成方法でIr−516を合成した。得られたIr−516について、合成例1及び2で得たイリジウム錯体と同様に同定を行い構造を確認すると共に、PLスペクトル測定により最大発光ピーク波長測定を行った。結果を表1に示す。
下記に示す合成スキームにより、4−ジベンゾチオフェンボロン酸を出発原料として、Pd触媒を用いたクロスカップリング反応を用いて、例示化合物H−108、H−131及びH−139をそれぞれ合成した。
下記に示す合成スキームにより、ベンゾ[b]ナフト[2,1−d]チオフェン−10−ボロン酸を合成し、続いてPd触媒を用いたクロスカップリング反応を行うことにより例示化合物H−206及びH−210をそれぞれ合成した。
下記に示す合成スキームにより、2−クロロベンゾ[b]フェナントロ[3,4−d]チオフェンを合成し、続いてPd触媒を用いたクロスカップリング反応を行うことにより例示化合物H−317及びH−322をそれぞれ合成した。
非特許文献5を参考にして、下記に示す合成スキームにより、ジベンゾ[b,mn]キサンテン−7−ボロン酸を合成した。続いてPd触媒を用いたクロスカップリング反応を行うことにより、例示化合物H−401、H−422及びH−424をそれぞれ合成した。
合成例27において、出発原料を9−ヒドロキシフェナントレンから3,6−ジメチルフェナントレン−9−オールに変更したこと以外は、合成例27と同様の方法により例示化合物H−439を合成した。MALDI−TOF−MSにて得られた化合物(例示化合物H−439)の同定を行った。結果を表2に示す。
下記に示す合成スキームにより、5−クロロジベンゾ[b,mn]キサンテンを合成し、続いてPd触媒を用いたクロスカップリング反応を行うことにより例示化合物H−507、H−508及びH−509を合成した。
合成例22において、出発原料を2−ブロモベンゾ[b]チオフェンから2−ブロモベンゾフランに変更したこと以外は、合成例22と同様の方法により例示化合物H−629を合成した。
下記に示す合成スキームにより例示化合物H−712を合成した。
本実施例では、基板上に、陽極/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極がこの順に設けられた構成の有機発光素子を以下に示す方法で作製した。
実施例1において、正孔輸送層(HTL)、電子阻止層(EBL)、発光層ホスト(HOST)、発光層ゲスト(GUEST)、正孔阻止層(HBL)及び電子輸送層(ETL)として用いた化合物を、下記表4に示される化合物に適宜変更した。これを除いては、実施例1と同様の方法により有機発光素子を作製した。得られた素子について実施例1と同様に素子の特性を測定・評価した。測定の結果を表4に示す。
本実施例では、基板上に、陽極/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極がこの順に設けられた構成の有機発光素子を作製した。尚、本実施例において、発光層にはアシスト材料が含まれている。
実施例27において、正孔輸送層(HTL)、電子阻止層(EBL)、発光層ホスト(HOST)、発光層アシスト(ASSIST)、発光層ゲスト(GUEST)、正孔阻止層(HBL)及び電子輸送層(ETL)に用いた化合物を、表6の通りに変更した。これを除いては、実施例27と同様の方法により有機発光素子を作製した。得られた素子について実施例27と同様に素子の特性を測定・評価した。測定の結果を表6に示す。
Claims (24)
- 一対の電極と、前記一対の電極の間に配置される有機化合物層と、を有し、
前記有機化合物層が、下記一般式[1]で示されるイリジウム錯体と、下記一般式[21]で示されるヘテロ環含有化合物と、を有することを特徴とする有機発光素子。
mは、1乃至3の整数を表し、nは、0乃至2の整数を表す。ただしm+nは、3である。
環Aは、ベンゼン環、ナフタレン環、フルオレン環、フェナンスレン環及び9,9−スピロビフルオレン環から選ばれる環状構造を表し、ベンゾ[f]イソキノリン骨格及びIr金属と共有結合している。尚、環Aは、さらに置換基を有してもよい。
Xは、二座配位子を表す。
部分構造IrXnは、下記一般式[2]乃至[4]に示される構造のいずれかである。
Ar1は、ナフタレンジイル基、フェナンスレンジイル基、アントラセンジイル基、ベンゾ[a]アントラセンジイル基、フルオレンジイル基、ベンゾ[a]フルオレンジイル基、ベンゾ[b]フルオレンジイル基、ベンゾ[c]フルオレンジイル基、ジベンゾ[a,c]フルオレンジイル基、ジベンゾ[b,h]フルオレンジイル基、ジベンゾ[c,g]フルオレンジイル基、ビフェニレンジイル基、アセナフチレンジイル基、クリセンジイル基、ベンゾ[b]クリセンジイル基、ピレンジイル基、ベンゾ[e]ピレンジイル基、トリフェニレンジイル基、ベンゾ[a]トリフェニレンジイル基、ベンゾ[b]トリフェニレンジイル基、ピセンジイル基、フルオランテンジイル基、ベンゾ[a]フルオランテンジイル基、ベンゾ[b]フルオランテンジイル基、ベンゾ[j]フルオランテンジイル基、ベンゾ[k]フルオランテンジイル基、ペリレンジイル基及びナフタセンジイル基から選択される2価の芳香族炭化水素基を表す。尚、当該2価の芳香族炭化水素基は、置換基をさらに有していてもよい。
Ar2は、ナフチル基、フェナントリル基、アントリル基、ベンゾ[a]アントリル基、フルオレニル基、ベンゾ[a]フルオレニル基、ベンゾ[b]フルオレニル基、ベンゾ[c]フルオレニル基、ジベンゾ[a,c]フルオレニル基、ジベンゾ[b,h]フルオレニル基、ジベンゾ[c,g]フルオレニル基、ビフェニレニル基、アセナフチレニル基、クリセニル基、ベンゾ[b]クリセニル基、ピレニル基、ベンゾ[e]ピレニル基、トリフェニレニル基、ベンゾ[a]トリフェニレニル基、ベンゾ[b]トリフェニレニル基、ピセニル基、フルオランテニル基、ベンゾ[a]フルオランテニル基、ベンゾ[b]フルオランテニル基、ベンゾ[j]フルオランテニル基、ベンゾ[k]フルオランテニル基、ペリレニル基及びナフタセニル基から選択される1価の芳香族炭化水素基を表す。尚、当該1価の芳香族炭化水素基は、置換基をさらに有していてもよい。
pは、1乃至4の整数を表す。pが2以上の場合、複数のAr1は同一であっても異なっていてもよい。〕 - 前記一般式[21]に示されるヘテロ環含有化合物において、
前記pが1であり、
前記Ar1が、置換あるいは無置換のナフタレンジイル基、置換あるいは無置換のフルオレンジイル基、置換あるいは無置換のフェナンスレンジイル基、置換あるいは無置換のクリセンジイル基又は置換あるいは無置換のトリフェニレンジイル基であり、
前記Ar2が、置換あるいは無置換のナフチル基、置換あるいは無置換のフルオレニル基、置換あるいは無置換のフェナンスレニル基、置換あるいは無置換のクリセニル基又は置換あるいは無置換のトリフェニレニル基であることを特徴とする、請求項1に記載の有機発光素子。 - 前記一般式[21]に示されるヘテロ環含有化合物において、
前記E1乃至E3が水素原子であることを特徴とする、請求項1又は2に記載の有機発光素子。 - 前記有機化合物層が、ホストとゲストとを有する発光層であり、
前記ゲストが、前記一般式[1]で示されるイリジウム錯体であり、
前記ホストが、前記一般式[21]で示されるヘテロ環含有化合物であることを特徴とする、請求項1乃至3のいずれか一項に記載の有機発光素子。 - 一対の電極と、前記一対の電極の間に配置される有機化合物層と、を有し、
前記有機化合物層が、下記一般式[1]で示されるイリジウム錯体と、下記一般式[5]で示されるヘテロ環含有化合物と、を有することを特徴とする有機発光素子。
mは、1乃至3の整数を表し、nは、0乃至2の整数を表す。ただしm+nは、3である。
環Aは、ベンゼン環、ナフタレン環、フルオレン環、フェナンスレン環及び9,9−スピロビフルオレン環から選ばれる環状構造を表し、ベンゾ[f]イソキノリン骨格及びIr金属と共有結合している。尚、環Aは、さらに置換基を有してもよい。
Xは、二座配位子を表す。
部分構造IrXnは、下記一般式[2]乃至[4]に示される構造のいずれかである。
Y1及びY2は、それぞれアルキル基又は置換あるいは無置換の芳香族炭化水素基を表す。
aは、0乃至4の整数を表す。aが2以上の場合、複数のY1は同一であっても異なっていてもよい。
bは、0乃至4の整数を表す。ただし環B2がベンゼン環である場合、bは、0乃至3の整数である。bが2以上の場合、複数のY2は同一であっても異なっていてもよい。
Ar1は、置換あるいは無置換の2価の芳香族炭化水素基を表す。
Ar2は、置換あるいは無置換の1価の芳香族炭化水素基を表す。
pは、0乃至4の整数を表す。pが2以上の場合、複数のAr1は同一であっても異なっていてもよい。〕 - 前記一般式[22]乃至[25]に示されるヘテロ環含有化合物において、
前記pが1であり、
前記Ar1が、置換あるいは無置換のフェニレン基、置換あるいは無置換のビフェニレン基、置換あるいは無置換のターフェニレン基、置換あるいは無置換のナフタレンジイル基、置換あるいは無置換のフルオレンジイル基、置換あるいは無置換のフェナンスレンジイル基、置換あるいは無置換のクリセンジイル基又は置換あるいは無置換のトリフェニレンジイル基であり、
前記Ar2が、置換あるいは無置換のフェニル基、置換あるいは無置換のビフェニル基、置換あるいは無置換のターフェニル基、置換あるいは無置換のナフチル基、置換あるいは無置換のフルオレニル基、置換あるいは無置換のフェナンスレニル基、置換あるいは無置換のクリセニル基又は置換あるいは無置換のトリフェニレニル基であることを特徴とする、請求項6乃至9のいずれか一項に記載の有機発光素子。 - 前記一般式[22]乃至[25]に示されるヘテロ環含有化合物において、
前記E4乃至E22が水素原子であることを特徴とする、請求項6乃至10のいずれか一項に記載の有機発光素子。 - 前記有機化合物層が、ホストとゲストとを有する発光層であり、
前記ゲストが、前記一般式[1]で示されるイリジウム錯体であり、
前記ホストが、前記一般式[5]で示されるヘテロ環含有化合物であることを特徴とする、請求項5乃至11のいずれか一項に記載の有機発光素子。 - 前記有機化合物層に、前記ホスト及び前記ゲストとは異なるアシスト材料がさらに含まれることを特徴とする、請求項4又は12に記載の有機発光素子。
- 前記アシスト材料がイリジウム錯体であることを特徴とする、請求項13に記載の有機発光素子。
- 前記一般式[1]で示されるイリジウム錯体において、
前記mが2であり、前記nが1であることを特徴とする、請求項1乃至14のいずれか一項に記載の有機発光素子。 - 前記一般式[1]で示されるイリジウム錯体が、下記一般式[6]で示されることを特徴とする、請求項1乃至15のいずれか一項に記載の有機発光素子。
mは、1乃至3の整数を表し、nは、0乃至2の整数を表す。ただしm+nは、3である。
*1は、環AとIr金属との結合を表し、*2は、環Aとベンゾ[f]イソキノリン骨格内の4位の炭素原子との結合を表す。
環Aは、下記一般式[7]乃至[11]に示される構造のいずれかである。
*1は、Ir金属との結合位置を表し、*2は、ベンゾ[f]イソキノリン骨格内の4位の炭素原子との結合位置を表す。〕〕 - 前記環Aが、前記一般式[7]に示される構造であることを特徴とする、請求項16に記載の有機発光素子。
- 赤色発光することを特徴とする、請求項1乃至18のいずれか一項に記載の有機発光素子。
- 複数の画素を有し、
前記画素が、請求項1乃至19のいずれか一項に記載の有機発光素子と、前記有機発光素子に接続されている能動素子と、を有することを特徴とする、表示装置。 - 画像を表示するための表示部と、
画像情報を入力するための入力部と、を有し、
前記表示部が、請求項20に記載の表示装置であることを特徴とする、情報処理装置。 - 請求項1乃至19のいずれか一項に記載の有機発光素子と、
前記有機発光素子に接続されているAC/DCコンバーター回路と、を有することを特徴とする照明装置。 - 感光体と、
前記感光体の表面を帯電させる帯電手段と、
前記感光体を露光して静電潜像を形成するための露光手段と、
前記感光体の表面に形成された静電潜像を現像するための現像手段と、を有する画像形成装置であって、
前記露光手段が、請求項1乃至19のいずれか一項に記載の有機発光素子を有することを特徴とする、画像形成装置。 - 感光体を露光するための露光装置であって、
前記露光装置が、請求項1乃至19のいずれか一項に記載の有機発光素子を有し、
前記有機発光素子が、所定の方向に沿って列を形成して配置されていることを特徴とする、露光装置。
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