JP5937002B2 - 有機発光ダイオードのための2−アザトリフェニレン物質 - Google Patents
有機発光ダイオードのための2−アザトリフェニレン物質 Download PDFInfo
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- JP5937002B2 JP5937002B2 JP2012510966A JP2012510966A JP5937002B2 JP 5937002 B2 JP5937002 B2 JP 5937002B2 JP 2012510966 A JP2012510966 A JP 2012510966A JP 2012510966 A JP2012510966 A JP 2012510966A JP 5937002 B2 JP5937002 B2 JP 5937002B2
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- azatriphenylene
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- 239000000463 material Substances 0.000 title description 72
- CYCGKTMTMXGLSE-UHFFFAOYSA-N phenanthro[9,10-c]pyridine Chemical group N1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 CYCGKTMTMXGLSE-UHFFFAOYSA-N 0.000 title description 39
- 150000001875 compounds Chemical class 0.000 claims description 201
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 125000001072 heteroaryl group Chemical group 0.000 claims description 61
- 239000003446 ligand Substances 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 125000003342 alkenyl group Chemical group 0.000 claims description 37
- 125000000304 alkynyl group Chemical group 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000003545 alkoxy group Chemical group 0.000 claims description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
- 238000006467 substitution reaction Methods 0.000 claims description 28
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 239000010410 layer Substances 0.000 description 92
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- 239000012044 organic layer Substances 0.000 description 35
- 150000002431 hydrogen Chemical class 0.000 description 25
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- -1 arylkyl Chemical group 0.000 description 18
- 230000000903 blocking effect Effects 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 18
- 239000002184 metal Substances 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 15
- 125000005580 triphenylene group Chemical group 0.000 description 15
- 239000007924 injection Substances 0.000 description 13
- 238000002347 injection Methods 0.000 description 13
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- 238000000034 method Methods 0.000 description 12
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- 125000001424 substituent group Chemical group 0.000 description 12
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- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 11
- 229940125904 compound 1 Drugs 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
- RIYPENPUNLHEBK-UHFFFAOYSA-N phenanthro[9,10-b]pyridine Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 RIYPENPUNLHEBK-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
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- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- 0 CC(C)(C=C1)C=Cc2c1c(C=C*(*)C=C1)c1c1c2C=NC(C)(*)C=C1C1=CC(C(c2c(C=C3)c(C=C(**)CC=C4)c4[s]2)=CC3(C)S)=CC(C)(*)C=C1 Chemical compound CC(C)(C=C1)C=Cc2c1c(C=C*(*)C=C1)c1c1c2C=NC(C)(*)C=C1C1=CC(C(c2c(C=C3)c(C=C(**)CC=C4)c4[s]2)=CC3(C)S)=CC(C)(*)C=C1 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- OBRCRADLHSQIGF-UHFFFAOYSA-N 2h-phenanthro[9,10-c]pyridin-3-one Chemical compound C1=CC=C2C3=CNC(=O)C=C3C3=CC=CC=C3C2=C1 OBRCRADLHSQIGF-UHFFFAOYSA-N 0.000 description 3
- CULMFALPCRDYCM-UHFFFAOYSA-N 3-phenylphenanthro[9,10-c]pyridine Chemical compound C1=CC=CC=C1C1=CC2=C(C=CC=C3)C3=C(C=CC=C3)C3=C2C=N1 CULMFALPCRDYCM-UHFFFAOYSA-N 0.000 description 3
- 238000003775 Density Functional Theory Methods 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 238000010586 diagram Methods 0.000 description 3
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
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- HTQKPETUMFKKIC-UHFFFAOYSA-N 2-(3-dibenzothiophen-4-ylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC(C=2C=3SC4=CC=CC=C4C=3C=CC=2)=C1 HTQKPETUMFKKIC-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
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- 238000006243 chemical reaction Methods 0.000 description 2
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- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical group [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 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- QJYBUUJZDHARPY-UHFFFAOYSA-N phenanthro[9,10-c]pyridin-3-yl trifluoromethanesulfonate Chemical compound C1=CC=CC2=C(C=NC(OS(=O)(=O)C(F)(F)F)=C3)C3=C(C=CC=C3)C3=C21 QJYBUUJZDHARPY-UHFFFAOYSA-N 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- HYCYKHYFIWHGEX-UHFFFAOYSA-N (2-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C1=CC=CC=C1 HYCYKHYFIWHGEX-UHFFFAOYSA-N 0.000 description 1
- FNHHVPPSBFQMEL-KQHDFZBMSA-N (3S)-5-N-[(1S,5R)-3-hydroxy-6-bicyclo[3.1.0]hexanyl]-7-N,3-dimethyl-3-phenyl-2H-1-benzofuran-5,7-dicarboxamide Chemical compound CNC(=O)c1cc(cc2c1OC[C@@]2(C)c1ccccc1)C(=O)NC1[C@H]2CC(O)C[C@@H]12 FNHHVPPSBFQMEL-KQHDFZBMSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical class C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- QKPLXUQYVDAZCT-UHFFFAOYSA-N 2-methoxy-4-(2-phenylphenyl)pyridine Chemical compound C1=NC(OC)=CC(C=2C(=CC=CC=2)C=2C=CC=CC=2)=C1 QKPLXUQYVDAZCT-UHFFFAOYSA-N 0.000 description 1
- KPDJYJYGEKVFJO-UHFFFAOYSA-N 3-(3-dibenzothiophen-4-ylphenyl)phenanthro[9,10-c]pyridine Chemical compound C1=CC=CC2=C(C=NC(C=3C=CC=C(C=3)C3=C4SC=5C(C4=CC=C3)=CC=CC=5)=C3)C3=C(C=CC=C3)C3=C21 KPDJYJYGEKVFJO-UHFFFAOYSA-N 0.000 description 1
- QHBNULPDPOHSIP-UHFFFAOYSA-N 3-methoxyphenanthro[9,10-c]pyridine Chemical compound C1=CC=CC2=C(C=NC(OC)=C3)C3=C(C=CC=C3)C3=C21 QHBNULPDPOHSIP-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical group C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- JVHWZEWMZMHZFN-UHFFFAOYSA-N 4-(3-bromophenyl)dibenzothiophene Chemical compound BrC1=CC=CC(C=2C3=C(C4=CC=CC=C4S3)C=CC=2)=C1 JVHWZEWMZMHZFN-UHFFFAOYSA-N 0.000 description 1
- LXMZGUADXGEKKL-UHFFFAOYSA-N 4-(3-bromophenyl)dibenzothiophene 2-(3-dibenzothiophen-4-ylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound BrC=1C=C(C=CC1)C1=CC=CC2=C1SC1=C2C=CC=C1.C1=CC=C(C=2SC3=C(C21)C=CC=C3)C=3C=C(C=CC3)B3OC(C(O3)(C)C)(C)C LXMZGUADXGEKKL-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 group 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
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- 239000004215 Carbon black (E152) Substances 0.000 description 1
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- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
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- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
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- 150000002503 iridium Chemical class 0.000 description 1
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- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- HLYTZTFNIRBLNA-LNTINUHCSA-K iridium(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ir+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O HLYTZTFNIRBLNA-LNTINUHCSA-K 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
- 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 1
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 229940062627 tribasic potassium phosphate Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
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Description
本出願は、2009年5月12日に出願した米国仮出願No.61/177,435号に対する優先権を主張し、それらの開示を、その全体を参照により本明細書に明示して援用する。
本発明は、有機発光デバイスに有利に用いることができる新規な有機物質に関する。より詳細には、本発明は、新規な2−アザトリフェニレン含有化合物及びそのような化合物を含むデバイスに関する。
新規な有機化合物を提供する。この化合物は、OLEDに有利に用いることができる2−アザトリフェニレン含有化合物を包含する。特にこれらの化合物は、ホスト物質、正孔阻止物質、又は発光性金属錯体のための配位子として用いることができる。本明細書において提供される2−アザトリフェニレン化合物を含むデバイスは、向上した安定性と効率を有しうる。新規な化合物を提供し、その化合物は以下の構造:
一般にOLEDは、アノードとカソードの間に配置され且つこれらと電気的に接続された少なくとも1つの有機層を含む。電流が流された場合、その有機層(一つ又は複数)中にアノードは正孔を注入し、カソードは電子を注入する。注入された正孔と電子は、それぞれ反対に帯電した電極に向かって移動する。同じ分子上に電子と正孔が局在した場合、励起エネルギー状態を有する、局在化した電子-正孔対である「励起子」が形成される。この励起子が発光機構によって緩和する時に光が発せられる。ある場合には、励起子はエキシマー又はエキシプレックス上に局在することもできる。非放射機構、例えば熱緩和も起こることがあるが、通常は好ましくないと考えられている。
及び、Baldoら,“Very high-efficiency green organic light-emitting devices based on electrophosphorescence”, Appl. Phys. Lett., vol. 75, No. 3, 4-6 (1999)(“Baldo-II”)、これらを参照により全体を援用する。リン光は、米国特許第7,279, 704号明細書の第5〜6欄により詳細に記載されており、これを参照により援用する。
式中、Rx及びRyは、モノ、ジ、トリ、又はテトラ置換を表すことができる。Rx及びRyは独立に、水素、アルキル、及びアリールからなる群から選択される。
4-クロロ-2-メトキシピリジン(3.0 g, 21.03 mmol)、2-ビフェニルボロン酸(5.0g, 25.23 mmol)、Pd2(dba)3(381 mg, 0.414 mmol)、2-ジシクロへキシルホスフィノ-2’,6’-ジメトキシビフェニル(681 mg, 1.66 mmol)、トルエン(250 mL)、及び水(25 mL)中のK3PO4・H2O(14.57 g, 63.09 mmol)の混合物(窒素でフラッシュしたもの)を18時間還流させた。この混合物を室温まで冷やした後、有機層を無水Na2SO4上で乾燥させ、濾過し、減圧下で濃縮した。残留物をシリカ(ヘキサン:酢酸エチル)上でのフラッシュクロマトグラフィーによって精製し、酢酸エチルから再結晶して4-(ビフェニル-2-イル)-2-メトキシピリジン(4.2 g、76.5%)を得た。
4-(ビフェニル-2-イル)-2-メトキシピリジン(2.9 g, 10.9 mmol)、ヨウ素(281 mg, 1.1 mmol)、及びトルエンを、磁気撹拌機、空気バブラー、及び紫外線ランプを備えた二重壁石英製光化学反応装置に仕込んだ。その溶媒中に穏やかに空気をバブリングさせながら、15時間光照射した。反応混合物をシリカ(ヘキサン:酢酸エチル)上でのフラッシュクロマトグラフィーによって精製し、MeOH中で超音波照射して3-メトキシジベンゾ[f,h]イソキノリンを得た(0.5 g, 17%)。
3-メトキシジベンゾ[f,h]イソキノリン(1.0 g, 3.9 mmol)とピリジン塩酸塩(4.5 g, 39 mmol)を約220℃で1.5時間加熱した。反応物を冷やし、水を添加した。得られた固体を濾過し、水で洗い、真空乾燥してジベンゾ[f,h]イソキノリン-3-オール(0.91 g, 95%)を得た。
無水トリフルオロメタンスルホン酸(5.2 g, 19 mmol)を、ジベンゾ[f,h]イソキノリン-3-オール(0.91 g, 3.7 mmol)、ピリジン(1.2 g, 15 mmol)、及びジクロロメタン100mLの混合物に窒素下で0℃にて添加し、室温で夜通し撹拌した。反応を飽和NaHCO3で止めた。有機層を水で洗い、Na2SO4上で乾燥させた。残留物をシリカ上のフラッシュクロマトグラフィー(ヘキサン:酢酸エチル)で精製し、生成物を得た(1.1 g, 79%)。
1,3-ジブロモベンゼン(18.63 g, 78.92 mmol)、ジベンゾ[b,d]チオフェン-4-イルボロン酸(6.0 g, 26.3 mmol)、Pd(PPh3)4(304 mg, 0.414 mmol)、トルエン(200 mL)、及び水(20 mL)中のK2CO3(10.9 g, 78.92 mmol)の混合物(窒素をフラッシュさせたもの)を23時間還流させた。混合物を室温まで冷やした後、有機層を水で洗い、無水Na2SO4上で乾燥させ、濾過し、減圧下で濃縮した。残留物を減圧蒸留(Kugelrohr)と続いてのシリカ上でのフラッシュクロマトグラフィー(ヘキサン:ジクロロメタン)によって精製して、4-(3-ブロモフェニル)ジベンゾ[b,d]チオフェン(3.5 g, 39.2%)を得た。
4-(3-ブロモフェニル)ジベンゾ[b,d]チオフェン(2.4 g, 7.70 mmol)、4,4,4’, 4’,5,5,5’,5’-オクタメチル-2,2’-ビ(1,3,2-ジオキサボロラン)(3.58 g, 14 mmol)、Pd(dppf)Cl2(114 mg, 0.14 mmol)、及びKOAc(2.08
g, 21.2 mmol)をジオキサン(100 mL)中、90℃にて18時間加熱した。混合物を室温に冷やした後、酢酸エチルを添加し、有機層を水で洗い、食塩水で洗い、無水Na2SO4上で乾燥させ、濾過した。セライトをろ液に添加し、次に減圧下で濃縮した。残留物をフラッシュクロマトグラフィー(ヘキサン:ジクロロメタン)とそれに続く減圧蒸留(Kugelrohr)により、過剰な4,4,4’, 4’,5,5,5’,5’-オクタメチル-2,2’-ビ(1,3,2-ジオキサボロラン)を除去し、次にヘキサン:酢酸エチルから再結晶して、2-(3-(ジベンゾ[b,d]チオフェン-4-イル)フェニル)-4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン(1.62 g, 59%)を得た。
工程4の生成物であるジベンゾ[f,h]イソキノリン-3-イル トリフルオロメタンスルホネート(1.1 g, 2.9 mmol)、工程6の生成物である2-(3-(ジベンゾ[b,d]チオフェン-4-イル)フェニル)-4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン(1.5 g, 3.8 mmol)、三塩基性リン酸カリウム一水和物(2.0 g, 8.8 mmol)、150mLのトルエン、及び15mLの水の混合物を調製し、20分間窒素でバブリングした。次にトリス(ジベンジリデンアセトン)ジパラジウム(0)(27 mg, 0.029 mmol)及び2-ジシクロへキシルホスフィノ-2’,6’-ジメトキシビフェニル(48 mg, 0.12 mmol)をその混合物に添加した。反応混合物を窒素でさらに20分間バブリングし、次に夜通し還流させた。室温まで冷やした後、2-(3-(ジベンゾ[b,d]チオフェン-4-イル)フェニル)-4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン(1.3 g, 3.4 mmol)、トリス(ジベンジリデンアセトン)ジパラジウム(0)(60 mg, 0.066 mmol)、及び2-ジシクロへキシルホスフィノ-2’,6’-ジメトキシビフェニル(100 mg, 0.24 mmol)をその混合物に添加した。反応混合物に窒素を30分間バブリングし、次に夜通し還流させた。この混合物を次に室温まで冷やした。有機層を集めて、MgSO4で乾燥させた。粗生成物をシリカゲルカラムで精製して、白色固体の化合物1を得た(1.0 g, 71%収率)。
化合物1の合成の上記工程4で合成したジベンゾ[f,h]イソキノリン-3-イル トリフルオロメタンスルホネート化合物を、化合物1の合成の工程7に記載した鈴木反応条件下でフェニルボロン酸と反応させて、配位子3-フェニルジベンゾ[f,h]イソキノリンを得た。
エチレングリコール中でIr(acac)3と混合した3-フェニルジベンゾ[f,h]イソキノリン配位子を加熱して、窒素下で夜通し還流させて化合物79を得た。配位子とIr(acac)のモル比は約3.5対1である。
LEは発光効率であり、これはOLEDの輝度を駆動電流密度で割ったものとして定義される。EQEは外部量子効率であり、これは接合(ジャンクション)を通過した電子に対する光子の測定数の割合として定義される。PEは電力効率であり、発した全光束を全電力入力で割ったものとして定義される。L0は初期輝度であり、これは特定の電流密度における初期の明るさとして定義される。RT80%は寿命の尺度であり、これは40mA/cm2の一定電流密度において室温で、初期輝度L0がその値の80%に低下するのに必要な時間として定義される。
Claims (11)
- 前記配位子Lがホモレプティック化合物に含まれている請求項2に記載の化合物。
- 前記配位子がヘテロレプティック化合物に含まれている請求項2に記載の化合物。
- nが1である、請求項5に記載の化合物。
- nが2である、請求項5に記載の化合物。
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US12/778,362 US9005771B2 (en) | 2009-05-12 | 2010-05-12 | 2-azatriphenylene materials for organic light emitting diodes |
US12/778,362 | 2010-05-12 | ||
PCT/US2010/034479 WO2010132524A1 (en) | 2009-05-12 | 2010-05-12 | 2-azatriphenylene materials for organic light emitting diodes |
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US9005771B2 (en) | 2015-04-14 |
JP6025959B2 (ja) | 2016-11-16 |
EP2520571B1 (en) | 2016-08-17 |
KR101738534B1 (ko) | 2017-05-23 |
KR20170056035A (ko) | 2017-05-22 |
KR20120023780A (ko) | 2012-03-13 |
CN107325089B (zh) | 2021-07-13 |
KR101884581B1 (ko) | 2018-08-01 |
TWI541234B (zh) | 2016-07-11 |
EP2429997A1 (en) | 2012-03-21 |
EP2429997B1 (en) | 2014-01-15 |
CN107325089A (zh) | 2017-11-07 |
TW201111347A (en) | 2011-04-01 |
JP2016104745A (ja) | 2016-06-09 |
US20100289406A1 (en) | 2010-11-18 |
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