JP5454854B2 - 有機エレクトロルミネセンス素子のための新規物質 - Google Patents
有機エレクトロルミネセンス素子のための新規物質 Download PDFInfo
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- JP5454854B2 JP5454854B2 JP2008515076A JP2008515076A JP5454854B2 JP 5454854 B2 JP5454854 B2 JP 5454854B2 JP 2008515076 A JP2008515076 A JP 2008515076A JP 2008515076 A JP2008515076 A JP 2008515076A JP 5454854 B2 JP5454854 B2 JP 5454854B2
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- 239000000463 material Substances 0.000 title claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 79
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- 239000010410 layer Substances 0.000 claims description 40
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 22
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 20
- 239000002019 doping agent Substances 0.000 claims description 16
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- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 230000005525 hole transport Effects 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
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- KGXCHACLIFYNOP-VOTSOKGWSA-N [(e)-2-phenylethenyl]phosphane Chemical compound P\C=C\C1=CC=CC=C1 KGXCHACLIFYNOP-VOTSOKGWSA-N 0.000 claims description 3
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- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 claims description 2
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- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
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- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical class C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 8
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- 238000005859 coupling reaction Methods 0.000 description 7
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 6
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 5
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000005504 styryl group Chemical group 0.000 description 5
- 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
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- BRUOAURMAFDGLP-UHFFFAOYSA-N 9,10-dibromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=C(Br)C2=C1 BRUOAURMAFDGLP-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 150000001642 boronic acid derivatives Chemical class 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- YAXMWEZMAZJPJT-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,4-methanonaphthalene-5-boronic acid Chemical compound OB(O)C1=CC=CC2=C1C1CCC2C1 YAXMWEZMAZJPJT-UHFFFAOYSA-N 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
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- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- LOJUIJIETJSSJJ-UHFFFAOYSA-N (4,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-1-yl)boronic acid Chemical compound CC1(C)CCC(C)(C)C2=C1C(C)=CC=C2B(O)O LOJUIJIETJSSJJ-UHFFFAOYSA-N 0.000 description 2
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- JRCJYPMNBNNCFE-UHFFFAOYSA-N 1,6-dibromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=C(Br)C=CC2=C1 JRCJYPMNBNNCFE-UHFFFAOYSA-N 0.000 description 2
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ORYDPTDVQRQHQO-UHFFFAOYSA-N 5-bromo-1,2,3,4-tetrahydro-1,4-methanonaphthalene Chemical compound BrC1=CC=CC2=C1C1CCC2C1 ORYDPTDVQRQHQO-UHFFFAOYSA-N 0.000 description 2
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- IAAQMIBNRYWDOD-UHFFFAOYSA-N 9,10-bis(4,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-1-yl)anthracene Chemical compound C12=CC=CC=C2C(C2=CC=C(C3=C2C(CCC3(C)C)(C)C)C)=C(C=CC=C2)C2=C1C1=CC=C(C)C2=C1C(C)(C)CCC2(C)C IAAQMIBNRYWDOD-UHFFFAOYSA-N 0.000 description 2
- GWNJZSGBZMLRBW-UHFFFAOYSA-N 9,10-dinaphthalen-1-ylanthracene Chemical class C12=CC=CC=C2C(C=2C3=CC=CC=C3C=CC=2)=C(C=CC=C2)C2=C1C1=CC=CC2=CC=CC=C12 GWNJZSGBZMLRBW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
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- 125000004429 atom Chemical group 0.000 description 2
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- GGFKOVMZDAWYEX-UHFFFAOYSA-N dicyclohexyl-(1,3-dimethoxy-2-phenylcyclohexa-2,4-dien-1-yl)phosphane Chemical group C1CCCCC1P(C1CCCCC1)C1(OC)CC=CC(OC)=C1C1=CC=CC=C1 GGFKOVMZDAWYEX-UHFFFAOYSA-N 0.000 description 2
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- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
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- 229910052700 potassium Inorganic materials 0.000 description 2
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- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
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- 238000007645 offset printing Methods 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- GDISDVBCNPLSDU-UHFFFAOYSA-N pyrido[2,3-g]quinoline Chemical compound C1=CC=NC2=CC3=CC=CN=C3C=C21 GDISDVBCNPLSDU-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000006836 terphenylene 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
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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Description
Ar1は、出現毎に同一であるか異なり、1以上のR基により置換されていてもよい少なくとも14個の芳香族環原子を有する縮合アリール若しくはヘテロアリール基であり;
Xは、出現毎に同一であるか異なり、式(2)若しくは式(3)であり、
Yは、出現毎に同一であるか異なり、X、Ar3基若しくはN(Ar3)2基であって、2個のAr3基は、単結合若しくはO、S、N(R)若しくはC(R)2基により互いに結合していてもよく;
Ar2は、出現毎に同一であるか異なり、1以上のR基により置換されていてもよく、Qが結合している、アリール若しくはヘテロアリール基であるが、但し、Q基或いはH以外のR基の何れかが、Ar2-Ar1結合に対しオルト位で結合しており;
Ar3は、出現毎に同一であるか異なり、1以上のR基により置換されていてもよい芳香族若しくは複素芳香族環構造であり;
Qは、出現毎に同一であるか異なり、直鎖、分岐或いは環状アルキレン若しくはアルキリデン基であり、Ar2への2個の結合若しくは隣接するAr1への1個の結合とAr2への1個の結合とを形成し、そしてそれにより更なる環構造を形成し、;Qは、ここで、1〜20個のC原子を含み、R1基により置換されていてもよく、そして、1以上の隣接しないC原子は、N-R1、O、S、O-CO-O、CO-O-、CR1=CR1-若しくは-C≡C-で置き代えられていてもよく、また、1以上のH原子は、F、Cl、Br、I若しくはCNで置き代えられていてもよく;
Rは、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、1〜40個のC原子を有する直鎖アルキル或いはアルコキシ鎖、又は3〜40個のC原子を有する分岐或いは環状アルキル若しくはアルコキシ基(各鎖はR1により置換されていてもよく、そして、1以上の隣接しないC原子は、N-R1、O、S、O-CO-O、CO-O-、CR1=CR1-若しくは-C≡C-で置換されていてもよく、また、1以上のH原子は、F、Cl、Br、I若しくはCNで置き代えられていてもよい)であり、又は1以上のR1基により置換されていてもよい5〜40個の芳香族環原子を有する芳香族若しくは複素環式芳香族環構造、又は、2、3若しくは4個のこれらの構造の組み合わせであり;ここで、2以上のR基は、互いに更なるモノ若しくはポリ環状、脂肪族若しくは芳香族環構造を形成するものであってもよく;
R1は、出現毎に同一であるか異なり、H若しくは1〜20個のC原子を有する炭化水素基であって、脂肪族若しくは芳香族若しくは脂肪族及び芳香族の組合せであってよく、そして、1以上のH原子は、Fにより置き代えられてよく;
mは、出現毎に0若しくは1であり;
pは、出現毎に0、1若しくは2であり;
但し、以下の化合物は除く。
Aは、単結合、O、S、N(R)若しくはC(R)2を表し;
Ar3基は、出現毎に同一であるか異なり、1以上のR基により置換されていてよい5〜20個の芳香族環原子、好ましくは、1以上のR基により置換されていてよい6〜14個の芳香族環原子を有するアリール若しくはヘテロアリール基であり、特に好ましくは、夫々、1以上のR基により置換されていてよい1-ナフチル若しくは2-ナフチルである。
Zは、CR2、O、S、NR、PR、P(=O)R、SiR2若しくはCR2-CR2であり;
nは、1、2若しくは3であり、好ましくは2であり;
ダッシュ記号の結合は、Ar1単位への結合を意味する。
以下の合成は、他に断らない限り、保護ガス雰囲気下で行われる。出発物質は、アルドリッチ(ALDRICH)或いはABCRから購入することができる(トリス(ジベンジリデンアセトン)ジパラジウム(0)、2-ジシクロヘキシルホスフィノ-2,6-ジメトキシビフェニル、9,10-ジブロモアントラセン、1,6-ジブロモピレン、1,3,6,8-テトラブロモピレン、無機物、溶媒)。5-ブロモ-1,2,3,4-テトラヒドロ-1,4-メタノナフタレンは、Tanida et al., J. Am. Chem. Soc. 1965, 87(21), 4794,の方法により調製され、5-ブロモ-1,1,4,4-テトラメチル-1,2,3,4-テトラヒドロ-8-メチルナフタレンは、Garipova et al., Tetrahedron 2005, 61(20), 4755.の方法により、6-ブロモ-1,1,4,4-テトラメチル-1,2,3,4-テトラヒドロナフタレン同様に調製される。5-ブロモ-1,2,3,4-テトラヒドロナフタレンは、Synthetic Communications 1992, 22(8), 1095-1099.に記載のように合成される。(5,6,7,8-テトラヒドロ-1-ナフトイル)ボロン酸は、US2002/019527に記載されるように合成される。
a)1,1,4,4-テトラメチル-1,2,3,4-テトラヒドロ-8-メチルナフタレン-5ボロン酸
OLEDを、WO 04/058911に記載される一般的プロセスにより製造したが、これは、特別な状況(例えば、最適な効率と色を達成するための層の厚さの変化)に対する個々の場合において適合される。
正孔輸送層(HTL1):20nmの2,2’,7,7’-テトラキス(ジ-パラ-トリルアミノ)-スピロ-9,9’-ビフルオレン(蒸着)、
正孔輸送層(HTL2):20nmのNPB(N-ナフチル-N-フェニル-4,4’-ジアミノビフェニル)
発光層(EML):ドーパントE1(WO 06/000388により合成、蒸着)をx%ドープされた(表参照)母体材料としてのH1乃至H7の30nmの層
電子伝導体(ETC):20nm(蒸着AlQ3、SynTec社から購入したトリス(キノリノラート)アルミニウム(III))
陰極:150nmのAl上の1nmLiF。
Claims (10)
- 式(1)の化合物;
Ar1は、出現毎に同一であるか異なり、1以上のR基により置換されていてもよい、アントラセン、フェナントレン及びピレンからなる群より選択され、;
Xは、出現毎に同一であるか異なり、式(21)乃至(24)の構造から選択される基であり、
nは、1、2若しくは3であり;
ここで、ダッシュ記号の結合は、Ar 1 単位への結合を意味し;
Yは、出現毎に同一であるか異なり、
−X、
−Ar3基であって、ここで、Ar3基は、R基により置換されていてもよいし非置換でもよい5〜20個の芳香族環原子を有する複素環式芳香族環構造であり、または
−N(Ar3)2基であって、ここで、Ar3は、R基により置換されていてもよい芳香族若しくは複素環式芳香族環構造であり、2個のAr3基は、単結合若しくはO、S、N(R)若しくはC(R)2基により互いに結合していてもよく;
Rは、出現毎に同一であるか異なり、H、F、Cl、Br、I、CN、1〜40個のC原子を有する直鎖アルキル或いはアルコキシ鎖、又は3〜40個のC原子を有する分岐或いは環状アルキル若しくはアルコキシ基(各鎖はR1により置換されていてもよく、そして、1以上の隣接しないC原子は、N-R1、O、S、O-CO-O、CO-O-若しくは、-C≡C-で置き代えられていてもよく、また、1以上のH原子は、F、Cl、Br、I若しくはCNで置き代えられていてもよい)又は1以上のR1基により置換されていてもよい、5〜40個の芳香族環原子を有する芳香族若しくは複素環式芳香族環構造、又は、2、3若しくは4個のこれらの構造の組み合わせであり;ここで、2以上のR基は、互いに更なるモノ若しくはポリ環状、脂肪族若しくは芳香族環構造を形成するものであってもよく;
R1は、出現毎に同一であるか異なり、H若しくは1〜20個のC原子を有する炭化水素基であって、脂肪族若しくは芳香族若しくは脂肪族及び芳香族の組合せであってよく、
1以上のH原子は、Fにより置き代えられてよく;
mは、出現毎に0若しくは1であり;
pは、0である。 - Qが、ベンジル型プロトンを含まないように選択されるか、又は橋頭C原子が、Ar2に直接結合していることを特徴とする、請求項1又は2記載の化合物。
- 請求項1乃至3の何れか1項記載の少なくとも1つの化合物及び1以上のドーパントを含む混合物。
- ドーパントが、芳香族アントラセンアミン、芳香族アントラセンジアミン、芳香族ピレンアミン、芳香族ピレンジアミン、モノスチリルアミン、ジスチリルアミン、トリスチリルアミン、テトラスチリルアミン、スチリルホスフィン、スチリルエーテル及びアリールアミンのクラスから選ばれることを特徴とする、請求項4記載の混合物。
- 請求項1乃至5の何れか1項記載の化合物若しくは混合物の有機電子素子での使用。
- 陽極、陰極及び請求項1乃至5の何れか1項記載の少なくとも1つの化合物若しくは混合物を含む少なくとも1つの有機層を含む有機電子素子。
- 有機及びポリマー発光ダイオード(OLED、PLED)、有機電界効果トランジスタ(O-FET)、有機薄膜トランジスタ(O-TFT)、有機光放出トランジスタ(O-LET)、有機集積回路(O-IC)、有機太陽電池(O-SC)、有機電場消光素子(O-FQD)、光放出電子化学電池(LEC)、有機光受容器及び有機レーザーダイオード(O-laser)からなる群より選択されることを特徴とする、請求項7の有機電子素子。
- 発光層に加えて、正孔注入層、正孔輸送層、電荷障壁層、電子輸送層及び/又は電子注入層から選択される1以上の更なる層も存在することを特徴とする、請求項7または8記載の有機電子素子。
- 請求項1乃至3の何れか1項記載の化合物が、シングレット状態若しくはより高スピン多重項状態から発光するドーパントのための母体材料として、ドーパントとして、正孔輸送材料として、電子輸送材料として、若しくは正孔障壁材料として使用されることを特徴とする請求項7乃至9の何れか1項記載の有機電子素子。
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-
2005
- 2005-06-09 DE DE102005026651A patent/DE102005026651A1/de not_active Withdrawn
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2006
- 2006-05-16 JP JP2008515076A patent/JP5454854B2/ja active Active
- 2006-05-16 EP EP06753643.3A patent/EP1888707B1/de active Active
- 2006-05-16 US US11/916,070 patent/US8679645B2/en active Active
- 2006-05-16 WO PCT/EP2006/004609 patent/WO2006131192A1/de active Application Filing
- 2006-06-06 TW TW095120070A patent/TW200704751A/zh unknown
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US20090128009A1 (en) | 2009-05-21 |
EP1888707B1 (de) | 2017-08-09 |
DE102005026651A1 (de) | 2006-12-14 |
WO2006131192A1 (de) | 2006-12-14 |
US20140203215A1 (en) | 2014-07-24 |
US8679645B2 (en) | 2014-03-25 |
TW200704751A (en) | 2007-02-01 |
JP2008545762A (ja) | 2008-12-18 |
US9893292B2 (en) | 2018-02-13 |
EP1888707A1 (de) | 2008-02-20 |
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