JP6242817B2 - 有機エレクトロルミネッセンス素子のためのスピロビフルオレン化合物 - Google Patents
有機エレクトロルミネッセンス素子のためのスピロビフルオレン化合物 Download PDFInfo
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- JP6242817B2 JP6242817B2 JP2014556942A JP2014556942A JP6242817B2 JP 6242817 B2 JP6242817 B2 JP 6242817B2 JP 2014556942 A JP2014556942 A JP 2014556942A JP 2014556942 A JP2014556942 A JP 2014556942A JP 6242817 B2 JP6242817 B2 JP 6242817B2
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- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical class C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 title claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 148
- 125000003118 aryl group Chemical group 0.000 claims description 81
- 125000004432 carbon atom Chemical group C* 0.000 claims description 68
- 239000000463 material Substances 0.000 claims description 47
- -1 quaterphenyl Chemical compound 0.000 claims description 38
- 230000005525 hole transport Effects 0.000 claims description 35
- 239000011159 matrix material Substances 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 32
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- 238000002347 injection Methods 0.000 claims description 21
- 239000007924 injection Substances 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 12
- 125000004986 diarylamino group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 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 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
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- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
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- 238000010791 quenching Methods 0.000 claims description 3
- 125000005266 diarylamine group Chemical group 0.000 claims description 2
- 230000005684 electric field Effects 0.000 claims description 2
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- 238000007689 inspection Methods 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 1
- 239000011368 organic material Substances 0.000 claims 1
- 125000003367 polycyclic group Polymers 0.000 claims 1
- 239000010410 layer Substances 0.000 description 128
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- 230000015572 biosynthetic process Effects 0.000 description 21
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- 229920000642 polymer Polymers 0.000 description 17
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- 230000000903 blocking effect Effects 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 239000000412 dendrimer Substances 0.000 description 10
- 229920000736 dendritic polymer Polymers 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- OBARUOOPPWHZRQ-UHFFFAOYSA-N 9,9-dimethyl-n-(2-phenylphenyl)fluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1NC1=CC=CC=C1C1=CC=CC=C1 OBARUOOPPWHZRQ-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- GQXFSXMUBDPXBG-UHFFFAOYSA-N 4-bromo-9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=C2C=CC=C1Br GQXFSXMUBDPXBG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
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- 238000009472 formulation Methods 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
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- 125000005259 triarylamine group Chemical group 0.000 description 3
- 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 2
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- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- NYRQYDOTDXVFCO-UHFFFAOYSA-N n-(9,9-dimethylfluoren-2-yl)-n-(2-phenylphenyl)-9,9'-spirobi[fluorene]-4-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C2=C(C3(C4=CC=CC=C4C4=CC=CC=C43)C3=CC=CC=C32)C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 NYRQYDOTDXVFCO-UHFFFAOYSA-N 0.000 description 2
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
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- DRKHIWKXLZCAKP-UHFFFAOYSA-N 1-bromo-2-(2-bromophenyl)benzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1Br DRKHIWKXLZCAKP-UHFFFAOYSA-N 0.000 description 1
- ZTISECWDPWDTAH-UHFFFAOYSA-N 1-bromo-9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=C2C(Br)=CC=C1 ZTISECWDPWDTAH-UHFFFAOYSA-N 0.000 description 1
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- 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
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
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- 238000001126 phototherapy Methods 0.000 description 1
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- 125000006617 triphenylamine group Chemical class 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
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Description
Ar1は、出現毎に同一であるか異なり、夫々、1以上の基R5により置換されてよいフルオレン、スピロビフルオレン、ビフェニル、テルフェニル、クアテルフェニル、カルンバゾール、ジベンゾフランおよびジベンゾチオフェンより成る基から選ばれる6〜60個のC原子を有する芳香族もしくは複素環式芳香族環構造であって;ここで、Ar1とAr2は、基Eによって、互いに結合してもよく;
Ar2は、出現毎に同一であるか異なり、各場合に、1以上の基R5により置換されてもよい6〜60個のC原子を有する芳香族もしくは複素環式芳香族環構造であって;ここで、Ar1とAr2は、基Eによって、互いに結合してもよく;
ArSは、出現毎に同一であるか異なり、各場合に、1以上の基R5により置換されてもよい6〜60個のC原子を有する芳香族もしくは複素環式芳香族環構造であり;
Eは、出現毎に同一であるか異なり、単結合、C(R5)2、NR5、OまたはSであり;
R1、R2、R3、R4は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、Si(R6)3、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基(夫々は、1以上の基R6により置換されてよく、各場合に、1以上の隣接しないCH2基は、Si(R6)2、C=NR6、P(=O)(R6)、SO、SO2、NR6、O、SもしくはCONR6で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、BrもしくはIで置き代えられてよい。)または、各場合に、1以上の基R6により置換されてよい6〜60個のC原子を有する芳香族もしくは複素環式芳香族環構造、または1以上の基R6で置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基、または各場合に1以上の基R6で置換されてよい5〜60個の芳香族環原子を有するアラルキルもしくはヘテロアラルキル基より成る基から選ばれ;ここで、2個以上の隣接する置換基R1もしくはR2もしくはR3もしくはR4は、一以上の基R6により置換されてよいモノあるいはポリ環式の脂肪族環構造を随意に形成してもよく;
R5は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、Si(R6)3、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基(夫々は、1以上の基R6により置換されてよく、各場合に、1以上の隣接しないCH2基は、Si(R6)2、C=NR6、P(=O)(R6)、SO、SO2、NR6、O、SもしくはCONR6で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、BrもしくはIで置き代えられてよい。)または、各場合に、1以上の基R6により置換されてよい6〜60個のC原子を有する芳香族もしくは複素環式芳香族環構造、または1以上の基R6で置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基、または各場合に1以上の基R6で置換されてよい5〜60個の芳香族環原子を有するアラルキルもしくはヘテロアラルキル基より成る基から選ばれ;ここで、2個以上の隣接する置換基R5は、一以上の基R6により置換されてよいモノあるいはポリ環式の脂肪族環構造を随意に形成してもよく;
R6は、H、D、F、1〜20個のC原子を有する脂肪族炭化水素基、5〜30個のC原子を有する芳香族もしくは複素環式環構造より成る基から選ばれ、ここで、1以上のH原子は、DもしくはFで置き代えられてよく、ここで、2個以上の隣接する置換基R6は、モノ-あるいはポリ環式の脂肪族環構造を互いに形成してもよく;
iは、出現毎に同一であるか異なり、0または1であり;
mは、0、1または2であり;
nは、出現毎に同一であるか異なり、0、1、2、3または4であり;
p、qは、出現毎に同一であるか異なり、0または1であり;
r、sは、出現毎に同一であるか異なり、0、1、2、3または4であり、ここで、p+r≦4およびq+s≦4である。
基Ar1とAr2は、上記定義のとおり、基Eを介して互いに結合し、および
基Ar1とAr2は、出現毎に同一であるか異なり、各場合に、1以上の基R5により置換されてもよい6〜60個のC原子を有する芳香族もしくは複素環式芳香族環構造である。
Eは、出現毎に同一であるか異なり、単結合、またはC(R1)2、N(R1)、OもしくはSであり;
R1〜R4は、出現毎に同一であるか異なり、H、F、CN、1〜10個のC原子を有する直鎖アルキルもしくはアルコキシ基、3〜10個のC原子を有する分岐あるいは環状アルキルもしくはアルコキシ基(夫々は、1以上の基R6により置換されてよく、1以上の隣接しないCH2基は、Oで置き代えられてよく、ここで、1以上のH原子は、Fで置き代えられてよい。)または、各場合に、1以上の基R6により置換されてよい6〜24個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造より成る基から選ばれ
R5は、基R5が、Ar1またはAr2またはArsに結合するならば、出現毎に同一であるか異なり、H、F、CN、1〜10個のC原子を有する直鎖アルキル基、3〜10個のC原子を有する分岐あるいは環状アルキル基、または、それぞれ、1以上の基R6により置換されてよい5〜24個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造より成る基から選ばれるか;
または、式(20)〜(23)、(53)、(54)、(68)および(72)中で炭素ブリッジに結合するR5は、出現毎に同一であるか異なり、1〜10個のC原子を有する直鎖アルキル基、特に、メチルもしくは1以上の基R6により置換されてよいフェニル基;または、式(28)〜(31)、(40)〜(43)、または(55)〜(58)、(63)〜(66)および(71)および(73)中で窒素ブリッジに結合するR5は、1以上の基R6により置換されてよいフェニル基から選択され;
R6は、出現毎に同一であるか異なり、H、1〜10個のC原子を有する直鎖アルキル基、3〜10個のC原子を有する分岐あるいは環状アルキル基、または、6〜24個のC原子を有する芳香族環構造より成る基から選ばれ;
iは、0であり;
mは、0または1であり、好ましくは、0であり;
nは、0または1であり、
p+qは、0または1あり:
rは、0または1であり、
sは、0または1である。
(A)スズキ重合;
(B)ヤマモト重合;
(C)スチル重合および
(D)ハートウイッグ-ブッフバルト重合。
更に好ましい有機エレクトロルミネッセンス素子は、1以上の層が、昇華プロセスにより適用され、材料は、10−5mbar未満、好ましくは、10−6mbar未満の初期圧力で、真空昇華ユニット中で真空気相堆積されることを特徴とする。しかしながら、初期圧力は、さらにより低くても、たとえば、10−7mbar未満でも可能である。
A)合成例
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)またはABCRから購入することができる。文献から知られる出発材料の場合の角括弧内の番号は、対応するCAS番号である。
1-(1-ビフェン-4-イル)-(9,9’-ジメチルフルオレン-2-イル)アミン-9H-フルオレン-9-オンの合成
1,1’-ビス(ジフェニルホスフィノ)フェロセン(1.5g、2.7ミリモル)、酢酸パラジウム(616mg、2.7ミリモル)と、ナトリウムtert-ブトキシド(22.9g、238ミリモル)とを、脱気トルエン(400ml)中のビフェニル-2-イルアミン(31.0g、183ミリモル)と、2-ブロモ-9,9-ジメチル-9H-フルオレン(50.0g、183ミリモル)の溶液に添加し、その混合物を20時間、還流下で加熱する。反応混合物を室温まで冷まし、トルエンで増量し、セライトで濾過する。濾過物を水で増量し、トルエンで再抽出し、結合した有機相を真空で蒸発乾固させる。残留物をシリカゲルを通して濾過し(ヘプタン/ジクロロメタン)、イソプロパノールから結晶化させる。ビフェニル-2-イル-(9,9-ジメチル-9H-フルオレン-2-イル)アミンは淡黄色の固形形状で得られる(63.0g、理論値の95%)。
トリ-tert-ブチルホスフィン(トルエン中、4.4mlの1.0モル濃度の溶液、4.4ミリモル)と、酢酸パラジウム(248mg、1.1ミリモル)と、ナトリウムtert-ブトキシド(16.0g、166ミリモル)とを、脱気トルエン(500ml)中のビフェニル-2-イル-(9,9-ジメチル-9H-フルオレン-2-イル)アミン(40.0g、111ミリモル)と、4-ブロモ-9,9’-スピロビフルオレン(56.9g、144ミリモル)の溶液に添加し、その混合物を2時間、還流下で加熱する。反応混合物を室温まで冷まし、トルエンで増量し、セライトで濾過する。濾過物を真空で蒸発させ、残留物を酢酸エチル/ヘプタンから結晶化させる。粗生成物をソックスレー抽出器(トルエン)で抽出し、真空下で2度、ゾーン昇華により精製する(p=3×10−4mバール、T=298℃)。生成物を淡黄色の固形形状で単離させる(20.4g、理論値の27%、HPLCによる純度>99.99%)。
ビフェニル-4-イル-(9,9-ジメチル-9H-フルオレン-2-イル(4,4,5,5テトラメチル-[1,3,2]ジオキサボロラン-2-イル)-フェニル]-アミンの合成
本発明によるOLEDと先行技術によるOLEDが、WO 2004/058911にしたがう一般的プロセスにより製造されるが、ここに記載される状況(層の厚さの変化、材料)に適合される。
特に、本発明の化合物は、OLEDでのHIL,HTLもしくはEBLとして適している。それらは、単一層としてのならず、HIL,HTL、EBLとして混合成分として、またはEML内で適している。
一重項青色素子が、表1と2に示され、三重項緑色素子が、表3と4に示される。
異なる青色蛍光素子構造(表6)において、技術水準の材料(NPBとHTMV1)を使用する参照素子V5とV6は、本発明の化合物を含む素子E3(8.5%)、E4(8.3%)、E5(7.9%)、E6(7.6%)、E7(7.8%)、E8(8.9%)、E9(8.4%)、E10(8.1%)およびE11(8.2%)と比べて、より低い効率(V5に対して6.2%のEQE@10mA/cm2および V6に対して5.8%)を有する。
異なる緑色蛍光素子構造(表6)において、参照素子V7は、本発明の化合物を含む素子E12(20.0%)、E13(19.6%)、E14(18.9%)、E15(19.2%)およびE16(20.2%)と比べて、11.7%のより低い効率(EQE@2mA/cm2)を有する。参照素子V6は、また、試料E12(90h)、E13(185h)、E14(105h)、E15(205h)およびE16(185h)と比べて、80hのより短い寿命(LT80@20mA)を有する。
例4
異なる緑色燐光素子構造(表7)において、本発明の化合物を発光層のマトリックス材料として含まない参照素子V8は、EML中で混合マトリックス成分として使用される本発明の化合物HTM3を含む試料E17(16.1%のEQE@2mA/cm2)と比べてより低い効率(14.4%のEQE@2mA/cm2)を有する。参照試料V8は、また、330hの試料E17と比べて305hのより短い寿命(LT80@20mA)を有する。
異なる緑色燐光素子構造(表7)において、本発明の化合物は、ラクタム化合物H4と組み合わせて、発光層中の混合マトリックス成分として好ましい効果を示す。参照素子V9は、17.6%の効率(EQE@2mA/cm2)と255hの寿命を有する。V9と比べた例E18とE19により示されるとおりに、コマトリックス材料として本発明の化合物を発光層に添加することにより、寿命を改善することができる。素子E18は、13.4%の効率と400hの寿命を示し、素子E19は、17.9%の効率と270hの寿命を示し、参照素子V9と比べて、両者改善されている。
Claims (14)
- 以下の式(2a)、(5)または(8)の化合物;
Ar1は、出現毎に同一であるか異なり、夫々、1以上の基R5により置換されてよいフルオレン、スピロビフルオレン、ビフェニル、テルフェニル、クアテルフェニル、カルバゾール、ジベンゾフランおよびジベンゾチオフェンより成る基から選ばれる6〜60個のC原子を有する芳香族もしくは複素環式芳香族環構造であり;
Ar2は、出現毎に同一であるか異なり、各場合に、1以上の基R5により置換されてもよい6〜60個のC原子を有する芳香族環構造であって;
ArSは、出現毎に同一であるか異なり、各場合に、1以上の基R5により置換されてもよい6〜60個のC原子を有する芳香族もしくは複素環式芳香族環構造であり;
Eは、出現毎に同一であるか異なり、単結合、C(R5)2、NR5、OまたはSであり;
R1、R2、R3、R4は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、Si(R6)3、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基(夫々は、1以上の基R6により置換されてよく、各場合に、1以上の隣接しないCH2基は、Si(R6)2、C=NR6、P(=O)(R6)、SO、SO2、NR6、O、SもしくはCONR6で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、BrもしくはIで置き代えられてよい。)または、各場合に、1以上の基R6により置換されてよい6〜60個のC原子を有する芳香族もしくは複素環式芳香族環構造、または1以上の基R6で置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基、または各場合に1以上の基R6で置換されてよい5〜60個の芳香族環原子を有するアラルキルもしくはヘテロアラルキル基より成る基から選ばれ;ここで、2個以上の隣接する置換基R1もしくはR2もしくはR3もしくはR4は、一以上の基R6により置換されてよいモノあるいはポリ環式の脂肪族環構造を随意に形成してもよく;
ここで、式(5)および(8)において、R 1 、R 2 、R 3 およびR 4 が結合しない位置には、水素原子が結合し、
R5は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、Si(R6)3、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基(夫々は、1以上の基R6により置換されてよく、各場合に、1以上の隣接しないCH2基は、Si(R6)2、C=NR6、P(=O)(R6)、SO、SO2、NR6、O、SもしくはCONR6で置き代えられてよく、ここで、1以上のH原子は、D、F、Cl、BrもしくはIで置き代えられてよい。)または、各場合に、1以上の基R6により置換されてよい6〜60個のC原子を有する芳香族環構造、または1以上の基R6で置換されてよい5〜60個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基、または各場合に1以上の基R6で置換されてよい5〜60個の芳香族環原子を有するアラルキルもしくはヘテロアラルキル基より成る基から選ばれ;ここで、2個以上の隣接する置換基R5は、一以上の基R6により置換されてよいモノあるいはポリ環式の脂肪族環構造を随意に形成してもよく;
R6は、H、D、F、1〜20個のC原子を有する脂肪族炭化水素基、5〜30個のC原子を有する芳香族もしくは複素環式環構造より成る基から選ばれ、ここで、1以上のH原子は、DもしくはFで置き代えられてよく、ここで、2個以上の隣接する置換基R6は、モノ-あるいはポリ環式の脂肪族環構造を互いに形成してもよく;
iは、出現毎に同一であるか異なり、0または1であり;
mは、0、1または2であり;
nは、出現毎に同一であるか異なり、0、1、2、3または4であり;
r、sは、出現毎に同一であるか異なり、0、1、2、3または4であり;
または、上記定義に代えて、基Ar1とAr2に、以下の定義が適用されるという条件付きで式(2a)または(8)の化合物である:
基Ar1とAr2は、上記定義のとおり、基Eを介して互いに結合し、および基Ar1とAr2は、出現毎に同一であるか異なり、各場合に、1以上の基R5により置換されてもよい6〜60個のC原子を有する芳香族環構造である。 - 添え字iは、0であることを特徴とする、請求項1記載の化合物。
- Ar1およびAr2は、出現毎に同一であるか異なり、1以上の基R5により置換されてよい式(11)、(20)および(24)の基から選ばれることを特徴とする、請求項5記載の化合物。
- 基Ar1およびAr2は、互いに異なって選択されることを特徴とする、請求項1〜6何れか1項記載の化合物。
- R1〜R4は、出現毎に同一であるか異なり、H、F、CN、1〜10個のC原子を有する直鎖アルキルもしくはアルコキシ基、3〜10個のC原子を有する分岐あるいは環状アルキルもしくはアルコキシ基(夫々は、1以上の基R6により置換されてよく、1以上の隣接しないCH2基は、Oで置き代えられてよく、ここで、1以上のH原子は、Fで置き代えられてよい。)または、各場合に、1以上の基R6により置換されてよい6〜24個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造より成る基から選ばれることを特徴とする、請求項1〜7何れか1項記載の化合物。
- Ar1またはAr2またはArsに結合するR5は、出現毎に同一であるか異なり、H、F、CN、1〜10個のC原子を有する直鎖アルキル基、3〜10個のC原子を有する分岐あるいは環状アルキル基、または、それぞれ、1以上の基R6により置換されてよい5〜24個のC原子を有する芳香族環構造より成る基から選ばれることを特徴とする、請求項1〜8何れか1項記載の化合物。
- 以下であることを特徴とする、請求項1〜9何れか1項記載の化合物:
Ar1、Ar2は、出現毎に同一であるか異なり、式(11)〜(39)または(52)〜(58)の内の一つの基であるか;または-NAr1Ar2は、式(67)〜(72)または(74)の内の一つの基であり;
R1〜R4は、出現毎に同一であるか異なり、H、F、CN、1〜10個のC原子を有する直鎖アルキルもしくはアルコキシ基、3〜10個のC原子を有する分岐あるいは環状アルキルもしくはアルコキシ基(夫々は、1以上の基R6により置換されてよく、1以上の隣接しないCH2基は、Oで置き代えられてよく、ここで、1以上のH原子は、Fで置き代えられてよい。)または、各場合に、1以上の基R6により置換されてよい6〜24個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造より成る基から選ばれ
R5は、基R5が、Ar1またはAr2またはArsに結合するならば、出現毎に同一であるか異なり、H、F、CN、1〜10個のC原子を有する直鎖アルキル基、3〜10個のC原子を有する分岐あるいは環状アルキル基、または、それぞれ、1以上の基R6により置換されてよい5〜24個の芳香族環原子を有する芳香族環構造より成る基から選ばれるか;
または、式(20)〜(23)、(53)、(54)、(68)および(72)中で炭素ブリッジに結合するR5は、同一であるか異なり、1〜10個のC原子を有するアルキル基、特に、メチルもしくは1以上の基R6により置換されてよいフェニル基であるか;または、式(28)〜(31)または(55)〜(58)および(71)中で窒素ブリッジに結合するR5は、1以上の基R6により置換されてよいフェニル基であり;
R6は、出現毎に同一であるか異なり、H、1〜10個のC原子を有する直鎖アルキル基、3〜10個のC原子を有する分岐あるいは環状アルキル基、または、6〜24個のC原子を有する芳香族環構造より成る基から選ばれ;
iは、0であり;
mは、0または1であり、
nは、0または1であり、
rは、0または1であり、
sは、0または1である。 - ジアリールアミノ基が、1-もしくは3-もしくは4-ハロゲン化スピロビフルオレンとジアリールアミン間のC-Nカップリング反応により導入されることを特徴とする、請求項1〜10何れか1項記載の化合物の製造方法。
- 請求項1〜10何れか1項記載の化合物の電子素子での使用。
- 請求項1〜10何れか1項記載の少なくとも一つの化合物を含み、有機エレクトロルミネッセンス素子、有機集積回路、有機電界効果トランジスタ、有機薄膜トランジスタ、有機発光トランジスタ、有機太陽電池、有機染料感受性太陽電池、有機光学検査器、有機光受容器、有機電場消光素子、発光電子化学電池、有機レーザーダイオードおよび有機プラスモン発光素子より成る群から選ばれる電子素子。
- 請求項1〜10何れか1項記載の化合物が、正孔輸送もしくは正孔注入もしくは励起子ブロックもしくは電子ブロック層中で正孔輸送材料として含まれ、または、発光層中で蛍光もしくは燐光エミッターのためのマトリックス材料として含まれることを特徴とする、請求項13記載の素子。
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