JP2016516084A - 有機エレクトロルミッセンス素子のための材料の調製用の合成構築ブロック - Google Patents
有機エレクトロルミッセンス素子のための材料の調製用の合成構築ブロック Download PDFInfo
- Publication number
- JP2016516084A JP2016516084A JP2016504508A JP2016504508A JP2016516084A JP 2016516084 A JP2016516084 A JP 2016516084A JP 2016504508 A JP2016504508 A JP 2016504508A JP 2016504508 A JP2016504508 A JP 2016504508A JP 2016516084 A JP2016516084 A JP 2016516084A
- Authority
- JP
- Japan
- Prior art keywords
- groups
- group
- atoms
- aromatic
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000463 material Substances 0.000 title description 9
- 238000002360 preparation method Methods 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims description 93
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- -1 P (= O ) (R 1 ) Chemical compound 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 17
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 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
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000001118 alkylidene group Chemical group 0.000 claims description 6
- 239000003054 catalyst Substances 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
- 238000007339 nucleophilic aromatic substitution reaction Methods 0.000 claims description 6
- 125000004001 thioalkyl group Chemical group 0.000 claims description 6
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 5
- 239000012038 nucleophile Substances 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 150000001716 carbazoles Chemical group 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
- JTAUTNBVFDTYTI-UHFFFAOYSA-N 2-fluoro-1,3-dimethylbenzene Chemical group CC1=CC=CC(C)=C1F JTAUTNBVFDTYTI-UHFFFAOYSA-N 0.000 claims description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000005259 triarylamine group Chemical group 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- HQALDKFFRYFTKP-UHFFFAOYSA-N 2-[4-[4-(2-benzyl-1-benzothiophen-3-yl)phenyl]-2-bromo-6-(3-methoxyphenyl)phenoxy]acetic acid Chemical compound COC1=CC=CC(C=2C(=C(Br)C=C(C=2)C=2C=CC(=CC=2)C=2C3=CC=CC=C3SC=2CC=2C=CC=CC=2)OCC(O)=O)=C1 HQALDKFFRYFTKP-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001907 coumarones Chemical group 0.000 claims 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 claims description 2
- 150000002240 furans Chemical group 0.000 claims description 2
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical group C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 claims description 2
- 150000002475 indoles Chemical group 0.000 claims description 2
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical group C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 150000003577 thiophenes Chemical class 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- 239000000543 intermediate Substances 0.000 abstract description 3
- 239000011149 active material Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- PKJMCNWVFGYQRW-UHFFFAOYSA-N 5-bromo-2-fluorobenzene-1,3-dicarbonitrile Chemical compound FC1=C(C#N)C=C(Br)C=C1C#N PKJMCNWVFGYQRW-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 0 **1C=C(*)C(F)=C(*)C=C1 Chemical compound **1C=C(*)C(F)=C(*)C=C1 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- IDFLRCZOIXAMSZ-UHFFFAOYSA-N 5-tert-butyl-2-fluorobenzene-1,3-dicarbonitrile Chemical compound CC(C)(C)C1=CC(C#N)=C(F)C(C#N)=C1 IDFLRCZOIXAMSZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 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
- 125000006239 protecting group Chemical group 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 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 4
- 239000011701 zinc Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 238000000260 fractional sublimation Methods 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- JORVCRLRRRRLFI-UHFFFAOYSA-N 1,3-dichloro-2-fluorobenzene Chemical compound FC1=C(Cl)C=CC=C1Cl JORVCRLRRRRLFI-UHFFFAOYSA-N 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
- XCPFHWVTZLIWRF-UHFFFAOYSA-N 5-bromo-2-fluorobenzene-1,3-dicarbonyl chloride Chemical compound FC1=C(C(Cl)=O)C=C(Br)C=C1C(Cl)=O XCPFHWVTZLIWRF-UHFFFAOYSA-N 0.000 description 2
- KBJOHAQIUYFQJJ-UHFFFAOYSA-N 5-bromo-2-fluorobenzene-1,3-dicarboxamide Chemical compound NC(=O)C1=CC(Br)=CC(C(N)=O)=C1F KBJOHAQIUYFQJJ-UHFFFAOYSA-N 0.000 description 2
- HXTYPCYLVFPBCQ-UHFFFAOYSA-N 5-bromo-2-fluorobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(Br)=CC(C(O)=O)=C1F HXTYPCYLVFPBCQ-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 2
- 235000019798 tripotassium phosphate Nutrition 0.000 description 2
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-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 1
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 1
- HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical compound C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 1
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- AAIJEURQKZASKQ-UHFFFAOYSA-N 1-fluoro-2,4-dimethylbenzene Chemical group CC1=CC=C(F)C(C)=C1 AAIJEURQKZASKQ-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- USYCQABRSUEURP-UHFFFAOYSA-N 1h-benzo[f]benzimidazole Chemical compound C1=CC=C2C=C(NC=N3)C3=CC2=C1 USYCQABRSUEURP-UHFFFAOYSA-N 0.000 description 1
- IGHOZKDBCCFNNC-UHFFFAOYSA-N 1h-imidazole;quinoxaline Chemical compound C1=CNC=N1.N1=CC=NC2=CC=CC=C21 IGHOZKDBCCFNNC-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- PFRPMHBYYJIARU-UHFFFAOYSA-N 2,3-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),2,4,6,8(16),9,11(15),12-octaene Chemical compound C1=CC=C2N=NC3=CC=CC4=CC=C1C2=C43 PFRPMHBYYJIARU-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 1
- NXINXVRARMMZDP-UHFFFAOYSA-N 2-fluoro-5-phenylbenzene-1,3-dicarbonitrile Chemical compound C1=C(C#N)C(F)=C(C#N)C=C1C1=CC=CC=C1 NXINXVRARMMZDP-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- CPDDXQJCPYHULE-UHFFFAOYSA-N 4,5,14,16-tetrazapentacyclo[9.7.1.12,6.015,19.010,20]icosa-1(18),2,4,6,8,10(20),11(19),12,14,16-decaene Chemical group C1=CC(C2=CC=CC=3C2=C2C=NN=3)=C3C2=CC=NC3=N1 CPDDXQJCPYHULE-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- IUKNPBPXZUWMNO-UHFFFAOYSA-N 5,12-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4,6,8(16),9,11,13-octaene Chemical compound N1=CC=C2C=CC3=NC=CC4=CC=C1C2=C43 IUKNPBPXZUWMNO-UHFFFAOYSA-N 0.000 description 1
- NHWJSCHQRMCCAD-UHFFFAOYSA-N 5,14-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),2,4,6,8(16),9,11(15),12-octaene Chemical compound C1=CN=C2C=CC3=NC=CC4=CC=C1C2=C43 NHWJSCHQRMCCAD-UHFFFAOYSA-N 0.000 description 1
- ZXPHUVHMBKRRJF-UHFFFAOYSA-N 5-bromo-2-fluoro-1,3-dimethylbenzene Chemical group CC1=CC(Br)=CC(C)=C1F ZXPHUVHMBKRRJF-UHFFFAOYSA-N 0.000 description 1
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- ZPQQFEPXKTVQLP-UHFFFAOYSA-N C1=NN=C2C=CC3=CC=CC4=CC=C1C2=C34.C3=NC=C4C=CC2=CN=CC1=CC=C3C4=C21 Chemical compound C1=NN=C2C=CC3=CC=CC4=CC=C1C2=C34.C3=NC=C4C=CC2=CN=CC1=CC=C3C4=C21 ZPQQFEPXKTVQLP-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 101100406879 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) par-2 gene Proteins 0.000 description 1
- 102100033617 Retinal-specific phospholipid-transporting ATPase ABCA4 Human genes 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- VGRJHHLDEYYRNF-UHFFFAOYSA-N ac1lasce Chemical compound C1C2=CC=CC=C2C(C=2C3=CC=CC=C3CC=22)=C1C1=C2CC2=CC=CC=C21 VGRJHHLDEYYRNF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 125000005620 boronic acid group Chemical group 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007333 cyanation reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 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 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 125000004986 diarylamino group Chemical group 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 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 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 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
- 125000005981 pentynyl group Chemical group 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 125000005385 peroxodisulfate group Chemical group 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000002243 precursor Substances 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
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000006413 ring segment Chemical group 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
- 239000011780 sodium chloride Substances 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
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/20—Preparation of carboxylic acid nitriles by dehydration of carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/95—Spiro compounds containing "not free" spiro atoms
- C07C2603/96—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members
- C07C2603/97—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members containing five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Electroluminescent Light Sources (AREA)
- Indole Compounds (AREA)
- Furan Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Materials Engineering (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Lは、単結合または2,3,4,5もしくは6価基であり;
Rは、出現毎に同一であるか異なり、H、D、Cl、Br、I、NAr2、N(R1)2(ここで、R1は、Hではない。)、C(=O)Ar、C(=O)R1、BR1、P(=O)Ar2、PAr2、OAr、SAr、S(=O)Ar、S(=O)2Ar、Si(R1)3、1〜40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、3〜40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、2〜40個のC原子を有するアルケニルもしくはアルキニル基(夫々1以上の基R1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、R1C=CR1、C≡C、Si(R1)2、C=NR1、P(=O)(R1)、NR1、O、SもしくはCONR1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R1により置換されてよい5〜60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;ここで、2個以上の隣接する置換基Rは、1以上の基R1により置換されてよい単環もしくは多環式の脂肪族、芳香族あるいは複素環式芳香族環構造を随意に形成してよく;
Arは、出現毎に同一であるか異なり、1以上の基R1により置換されてよい5〜30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であり;ここで、同じN原子もしくはP原子に結合する2つの基Arは、単結合により、またはN(R1)、C(R1)2、O、SもしくはBR1から選ばれるブリッジにより互いにブリッジされてもよく;
R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(R2)2、P(=O)(R2)2、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キル基、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キル基、2〜40個のC原子を有するアルケニルもしくはアルキニル基(夫々、1以上の基R2により置換されてよく、ここで、1以上の隣接しないCH2基は、R2C=CR2、C≡C、Si(R2)2、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SもしくはCONR2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、IもしくはCNで置き代えられてよい。)、または各場合に、1以上の基R2により置換されてよい5〜60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;ここで、2個以上の隣接する置換基R1は、1以上の基R2により置換されてよい単環もしくは多環式の脂肪族、芳香族あるいは複素環式芳香族環構造を随意に形成してよく;
R2は、出現毎に同一であるか異なり、H、D、F、CN、1〜20個のC原子を有する脂肪族炭化水素基、または5〜30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(さらに、1以上のH原子は、D、F、Cl、Br、IもしくはCNで置き代えられてよい。)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R2は、単環もしくは多環式の脂肪族環構造をたがいに形成してよく;
nは、0、1、2、3、4または5であり、ただし、nが0の場合にはLは存在せず、さらに、ただし、nが1以上の場合には、Lは、各場合に、基Rに代わりベンゼン骨格に結合し、それゆえに対応する基Rは存在せず:
ただし、以下の化合物は除外される。
Eは、C(R1)2、NR1、O、S、BR1またはSi(R1)2、好ましくは、NR1、OまたはSより成る基から選ばれる。
Aは、出現毎に同一であるか異なり、CR1またはNであり、ただし、2または3個の基Aは、Nであり;
Ar1は、出現毎に同一であるか異なり、1以上の基R1により置換されてよい5〜16個の芳香族環原子を有する2価の芳香族もしくは複素環式芳香族環構造であり;
mは、0または1である。
Gは、NR1、OまたはSより成る基から選ばれる。
a)フルオロ-メタ-キシレンの酸化によりカルボン酸を得る工程、および
b)カルボン酸官能基のニトリル基への変換工程。
以下の合成を、別段の指定がない限り、無水溶媒中で保護ガス雰囲気下で実施する。溶媒及び試薬を、たとえば、Sigma-ALDRICHまたはABCRから購入することができる。個々の化合物に対して示されている角括弧中のそれぞれの番号は、文献から公知ではあるが、市場で入手可能ではない化合物のCAS番号に関連する。
22.5g(100ミリモル)の5-ブロモ-2-フルオロイソフタロニトリル(S1)と、14.6g(120ミリモル)のフェニルボロン酸[98-80-6]と、42.5g(200ミリモル)のリン酸三カリウムと、1.8g(6ミリモル)のトリ-o-トリホスフィンと、224mg(1ミリモル)の酢酸パラジウム(II)と、200mlのトルエンと、50mlのジオキサンと、200mlの水との混合物を、5-ブロモ-2-フルオロイソフタロニトリル(S1)が消費されるまで(約6時間)還流下で加熱する。冷却後、水相を分離させ、有機相をセライトベッドを通して濾過してパラジウムを除去し、濾過物を各回、200mlの水で三度と、200mlの飽和塩化ナトリウム溶液で一度、洗浄し、硫酸マグネシウムで脱水させる。溶媒の除去後に得られた残留物を、DMFから二度、再結晶化させる。収率:15.1g(68ミリモル)68%。純度:1H−NMRによると約99%。
22.5g(100ミリモル)の5-ブロモ-2-フルオロイソフタロニトリル(S1)と、14.6g(120ミリモル)のフェニルボロン酸と、17.5g(300ミリモル)のフッ化カリウム、無水物と、263mg(1.3ミリモル)のトリ-tert-ブチルホスフィンと、224mg(1ミリモル)の酢酸パラジウム(II)と、250mlのTHFとの混合物を、5-ブロモ-2-フルオロイソフタロニトリル(S1)が消費されるまで(約2時間)還流下で加熱する。冷却後、混合物をセライトベッドを通して濾過し、200mlのTHFで濯いで塩とパラジウムとを除去する。濾過物を蒸発乾固させ、残留物を200mlの水/EtOH(1:1、vv)の混合物と共に撹拌することにより洗浄し、固形物を吸引濾過し、各回、100mlのエタノールで三度洗浄し、真空で乾燥させる。このようにして得られた固形物をDMFから二度、再結晶化させる。収率:16.9g(76ミリモル)76%。純度:1H−NMRによると約99%。反復する再結晶化またはクロマトグラフによって、および真空での分別昇華によって、さらに精製を行うことができる。
20.1g(120ミリモル)のカルバゾール[51555-21-6]を、200mlのTHF中で、鉱油中60重量%で分散させた、4.8g(120ミリモル)の水酸化ナトリウムの激しく撹拌した懸濁液に対して、氷冷しながら、約+10℃にて、小分けして、添加する−注意!水素の発生!起泡!。添加が完了したとき、混合物をさらに30分間撹拌し、20.2g(100ミリモル)を、2-フルオロ-5-tert-ブチルイソフタロニトリル(S6)と共に、次いで、温度が+20℃を超えない速度で氷冷しながら、小分けして添加する。添加が完了したとき、混合物を+10℃でさらに2時間撹拌し、その後、冷却槽を移動し、混合物を20−25℃に温めておき、さらに2時間撹拌し、次いで、40℃でさらに12時間温める。室温まで冷ました後、混合物を30mlのMeOHを滴下することによりクエンチし、次いで、反応混合物を真空中で、実質的に蒸発乾固させる。残留物を、100mlのメタノールと100mlの水との混合物で二度、次いで200mlのメタノールで一度、上昇温度で撹拌することにより洗浄する。DMFからの五度の再結晶化と、二度の分別昇華により精製を行う(p約1×10−5ミリバール、T約180℃)。収率:23.1g(66ミリモル)66%。純度:H−NMRによると約99.9。
変形例Aと類似の手順であるが、カルバゾールを最初にTHFに入れ、次いで、n−ヘキサン中、2.5モルの48ml(120ミリモル)のn−BuLiを滴下する。収率:20.6g(59ミリモル)59%。純度:H−NMRによると約99.9。
20.1g(120ミリモル)のカルバゾール[51555-21-6]を、20.2g(100ミリモル)の2-フルオロ-5-tert-ブチルイソフタロニトリル(S6)と、31.8g(150ミリモル)のリン酸三カリウム、無水物と、100gのガラスビーズと共に激しく撹拌した懸濁液を、300mlのジメチルアセトアミド中で160℃で16時間、撹拌する。冷却後、500mlの水を添加し、沈殿した固形物を吸引濾過し、各回、100mlの水で二度、各回、100mlのメタノールで二度、洗浄し、次いで真空で乾燥させる。変形例Aと同じように、さらに精製する。収率:22.0g(63ミリモル)63%。純度:H−NMRによると約99.9。
28mlのN,N-ジメチルアセトアミド中の2.81gの濃硫酸の3mlの混合物を、60mlのN,N-ジメチルアセトアミド中の、2.73g(5.7ミリモル)のX−Phosと643mg(2.9ミリモル)の酢酸パラジウム(II)の溶液に添加し、混合物を80℃で30分間撹拌し、その期間に暗茶色の溶液が形成される。
Claims (13)
- 式(1)、式(2)または式(3)の化合物;
Lは、単結合または2,3,4,5もしくは6価基であり;
Rは、出現毎に同一であるか異なり、H、D、Cl、Br、I、NAr2、N(R1)2(ここで、R1は、Hではない。)、C(=O)Ar、C(=O)R1、BR1、P(=O)Ar2、PAr2、OAr、SAr、S(=O)Ar、S(=O)2Ar、Si(R1)3、1〜40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、3〜40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、2〜40個のC原子を有するアルケニルもしくはアルキニル基(夫々1以上の基R1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、R1C=CR1、C≡C、Si(R1)2、C=NR1、P(=O)(R1)、NR1、O、SもしくはCONR1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R1により置換されてよい5〜60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;ここで、2個以上の隣接する置換基Rは、1以上の基R1により置換されてよい単環もしくは多環式の脂肪族、芳香族あるいは複素環式芳香族環構造を随意に形成してよく;
Arは、出現毎に同一であるか異なり、1以上の基R1により置換されてよい5〜30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であり;ここで、同じN原子もしくはP原子に結合する2つの基Arは、単結合により、またはN(R1)、C(R1)2、O、SもしくはBR1から選ばれるブリッジにより互いにブリッジされてもよく;
R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、CN、NO2、N(R2)2、P(=O)(R2)2、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キル基、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キル基、2〜40個のC原子を有するアルケニルもしくはアルキニル基(夫々、1以上の基R2により置換されてよく、ここで、1以上の隣接しないCH2基は、R2C=CR2、C≡C、Si(R2)2、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、SもしくはCONR2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、IもしくはCNで置き代えられてよい。)、または各場合に、1以上の基R2により置換されてよい5〜60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;ここで、2個以上の隣接する置換基R1は、1以上の基R2により置換されてよい単環もしくは多環式の脂肪族、芳香族あるいは複素環式芳香族環構造を随意に形成してよく;
R2は、出現毎に同一であるか異なり、H、D、F、CN、1〜20個のC原子を有する脂肪族炭化水素基、または5〜30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(さらに、1以上のH原子は、D、F、Cl、Br、IもしくはCNで置き代えられてよい。)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R2は、単環もしくは多環式の脂肪族環構造をたがいに形成してよく;
nは、0、1、2、3、4または5であり、ただし、nが0の場合にはLは存在せず、さらに、ただし、nが1以上の場合には、Lは、各場合に、基Rに代わりベンゼン骨格に結合し、それゆえに対応する基Rは存在せず:
ただし、以下の化合物は除外される。
- nは、0、1、2または3、好ましくは、0、1または2であることを特徴とする、請求項1記載の化合物。
- Lは、単結合、NR、BR、P(=O)R、1〜10個のC原子を有する直鎖アルキレンもしくはアルキリデン基、3〜10個のC原子を有する分岐あるいは環状アルキレンもしくはアルキリデン基(各場合に、一以以上の基Rにより置換されてよく、ここで1以上の隣接しないCH2基は、-RC=CR-、-C≡C-、Si(R)2、C=O、-O-、-S-もしくは-CONR-で置き代えられてよく、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い。)、または各場合に、1以上の基R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であることを特徴とする、請求項1または2記載の化合物。
- Rは、出現毎に同一であるか異なり、H、NAr2、C(=O)Ar、C(=O)R1、P(=O)Ar2、PAr2、Si(R1)3、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、2〜10個のC原子を有するアルケニル基(夫々、1以上の基R1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、R1C=CR1または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R1により置換されてよい5〜40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;ここで、2個以上の隣接する置換基Rは、1以上の基R1により置換されてよい単環もしくは多環式の脂肪族、芳香族あるいは複素環式芳香族環構造を随意に形成してよいことを特徴とする、請求項1〜5何れか1項記載の化合物。
- 基R、R1もしくはR2のいずれもが、6員環が互いに直接縮合した縮合アリールもしくはヘテロアリール基を含まないことを特徴とする、請求項1〜6何れか1項記載の化合物。
- 少なくとも一つの基Rは、1以上の基R1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;特に、ベンゼン、ビフェニル、特に、オルト-、メタ-もしくはパラ-ビフェニル、テルフェニル、特に、オルト-、メタ-、パラ-もしくは分岐テルフェニル、クアテルフェニル、特に、オルト-、メタ-、パラ-もしくは分岐クアテルフェニル、1-,2-,3-もしくは4-スピロビフルオレン、1-,2-,3-もしくは4-フルオレン、1-もしくは2-ナフチル、ピロール、フラン、チオフェン、インドール、ベンゾフラン、ベンゾチオフェン、カルバゾール、アザカルバゾール、ジベンゾフラン、ジベンゾチオフェン、ピリジン、ピリミジン、ピラジン、ピリダジン、トリアジン、イミダゾール、ベンズイミダゾール、ピラゾール、チアゾール、オキサゾール、オキサジアゾール、トリアゾール、フェナントレン、トリフェニレンまたは2もしくは3個のこれらの組み合わせから選ばれ、それぞれは、1以上の基R1により置換されてよいか、または少なくとも一つの置換基Rは、式(7)〜(18)の基の一つ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:
Aは、出現毎に同一であるか異なり、CR1またはNであり、ただし、1、2または3個の基Aは、Nであり;
Ar1は、出現毎に同一であるか異なり、1以上の基R1により置換されてよい5〜16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であり;
mは、0または1である。 - 少なくとも一つの基Rは、1以上の基R1により置換されてよいトリアリールアミン誘導体、カルバゾール誘導体、インデノカルバゾール誘導体、インドロカルバゾール誘導体、アザカルバゾール誘導体、インドール誘導体、フラン誘導体、ベンゾフラン誘導体、ジベンゾフラン誘導体、チオフェン誘導体、ベンゾチオフェン誘導体もしくはジベンゾチオフェン誘導体から選ばれるか、または少なくとも一つの置換基Rは、-NAr2であり、ここで2個の基Arは、NR1、O、S、C(R1)2、Si(R1)2もしくはBR1から選ばれる基、特に、式(19)〜(33)の基から選ばれる基により互いにブリッジされてもよいことを特徴とする、請求項1〜8何れか1項記載の化合物:
Gは、NR1、OまたはSから選ばれ
式中、各場合に、1または2個の基CR1は、Nにより置き代えられてよい。 - 以下の反応工程を含む、請求項1〜9何れか1項記載の化合物の製造方法:
a)フルオロ-メタ-キシレンの酸化によりカルボン酸を得る工程、および
b)カルボン酸官能基のニトリル基への変換工程。 - 触媒の存在下、フルオロ-メタ-ジハロベンゼン誘導体とZn(CN)2およびZnとの反応による、請求項1〜9何れか1項記載の化合物の製造方法。
- 請求項1〜9何れか1項記載の化合物の求核芳香族置換反応における出発材料としての使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP13001485.5 | 2013-03-22 | ||
EP13001485 | 2013-03-22 | ||
PCT/EP2014/000481 WO2014146750A1 (de) | 2013-03-22 | 2014-02-24 | Synthesebausteine für die herstellung von materialien für organische elektrolumineszenzvorrichtungen |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018237431A Division JP2019073520A (ja) | 2013-03-22 | 2018-12-19 | 有機エレクトロルミッセンス素子のための材料の調製用の合成構築ブロック |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2016516084A true JP2016516084A (ja) | 2016-06-02 |
JP6644673B2 JP6644673B2 (ja) | 2020-02-12 |
Family
ID=48013698
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016504508A Active JP6644673B2 (ja) | 2013-03-22 | 2014-02-24 | 有機エレクトロルミッセンス素子のための材料の調製用の合成構築ブロック |
JP2018237431A Withdrawn JP2019073520A (ja) | 2013-03-22 | 2018-12-19 | 有機エレクトロルミッセンス素子のための材料の調製用の合成構築ブロック |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018237431A Withdrawn JP2019073520A (ja) | 2013-03-22 | 2018-12-19 | 有機エレクトロルミッセンス素子のための材料の調製用の合成構築ブロック |
Country Status (6)
Country | Link |
---|---|
US (2) | US9718764B2 (ja) |
EP (1) | EP2976322B1 (ja) |
JP (2) | JP6644673B2 (ja) |
KR (1) | KR102256770B1 (ja) |
CN (2) | CN111718281A (ja) |
WO (1) | WO2014146750A1 (ja) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018113364A (ja) * | 2017-01-12 | 2018-07-19 | 日本放送協会 | 有機エレクトロルミネッセンス素子 |
WO2018181183A1 (ja) * | 2017-03-28 | 2018-10-04 | キヤノン株式会社 | 光学素子、材料、光学機器及び化合物 |
JP2019006767A (ja) * | 2017-06-21 | 2019-01-17 | 三星ディスプレイ株式會社Samsung Display Co.,Ltd. | ヘテロ環式化合物、及びそれを含んだ有機発光素子 |
WO2021066059A1 (ja) * | 2019-10-01 | 2021-04-08 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器 |
US11500129B2 (en) | 2017-03-28 | 2022-11-15 | Canon Kabushiki Kaisha | Optical element, material, optical apparatus and compound |
US11588111B2 (en) | 2017-08-04 | 2023-02-21 | Samsung Display Co., Ltd. | Condensed-cyclic compound and organic light-emitting device including the same |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3015457B1 (en) | 2013-06-26 | 2020-10-28 | Idemitsu Kosan Co., Ltd. | Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device |
CN104557532B (zh) * | 2015-01-13 | 2017-03-01 | 西安力邦制药有限公司 | 二联苯衍生物及其应用 |
WO2016116508A1 (de) * | 2015-01-20 | 2016-07-28 | Cynora Gmbh | Organische moleküle, insbesondere zur verwendung in optoelektronischen bauelementen |
CN107207434B (zh) * | 2015-01-20 | 2021-11-23 | 西诺拉股份有限公司 | 有机分子,特别是用于光电器件中的有机分子 |
EP3247768B1 (de) * | 2015-01-20 | 2019-03-13 | cynora GmbH | Naphthyl-substituierte organische moleküle zur verwendung in optoelektronischen bauelementen |
WO2016116524A2 (de) * | 2015-01-20 | 2016-07-28 | Cynora Gmbh | Organische moleküle zur verwendung in optoelektronischen bauelementen |
JP6596776B2 (ja) * | 2015-04-24 | 2019-10-30 | エルジー・ケム・リミテッド | 有機発光素子 |
WO2017005698A1 (de) * | 2015-07-03 | 2017-01-12 | Cynora Gmbh | Organische moleküle zur verwendung in organischen optoelektronischen vorrichtungen |
JP6738838B2 (ja) * | 2015-07-03 | 2020-08-12 | サイノーラ・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 有機光電子デバイスに使用するための有機分子 |
EP3113239A1 (de) * | 2015-07-03 | 2017-01-04 | cynora GmbH | Organische moleküle zur verwendung in organischen optoelektronischen vorrichtungen |
CN105085320B (zh) * | 2015-09-08 | 2017-03-22 | 北京大未来生物科技有限公司 | 一种二氰基取代联苯类化合物的合成方法 |
KR102509827B1 (ko) * | 2015-09-22 | 2023-03-15 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
EP3580300B1 (de) * | 2017-02-07 | 2020-10-21 | cynora GmbH | Organische moleküle, insbesondere zur verwendung in organischen optoelektronischen vorrichtungen |
KR102563713B1 (ko) | 2017-04-26 | 2023-08-07 | 오티아이 루미오닉스 인크. | 표면의 코팅을 패턴화하는 방법 및 패턴화된 코팅을 포함하는 장치 |
CN108947868B (zh) * | 2017-05-18 | 2021-02-23 | 山东师范大学 | 一种2,4-二氟苯腈的制备工艺 |
EP3418272B1 (en) * | 2017-06-21 | 2023-08-30 | Samsung Display Co., Ltd. | Triazine compounds and organic light-emitting devices including the same |
US11751415B2 (en) | 2018-02-02 | 2023-09-05 | Oti Lumionics Inc. | Materials for forming a nucleation-inhibiting coating and devices incorporating same |
KR20210149058A (ko) | 2019-03-07 | 2021-12-08 | 오티아이 루미오닉스 인크. | 핵생성 억제 코팅물 형성용 재료 및 이를 포함하는 디바이스 |
KR20220005359A (ko) | 2020-07-06 | 2022-01-13 | 삼성전자주식회사 | 헤테로시클릭 화합물 및 이를 포함한 유기 발광 소자 |
WO2022123431A1 (en) | 2020-12-07 | 2022-06-16 | Oti Lumionics Inc. | Patterning a conductive deposited layer using a nucleation inhibiting coating and an underlying metallic coating |
Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3331735A (en) * | 1963-04-01 | 1967-07-18 | Diamond Alkali Co | Halogenated aromatic pesticidal compositions for controlling fungi, bacteria and nematodes |
JPS513974A (ja) * | 1974-06-06 | 1976-01-13 | Diamond Shamrock Corp | Shokubutsuseichosokushinho |
US4556426A (en) * | 1983-06-13 | 1985-12-03 | Tile Council Of America, Inc. | Fungicidal grout composition |
JPS62240655A (ja) * | 1986-04-14 | 1987-10-21 | Sds Biotech Kk | イソフタロニトリル誘導体 |
JPS62294648A (ja) * | 1986-06-13 | 1987-12-22 | Sds Biotech Kk | フツ素含有芳香族ジエ−テル化合物及び該化合物からなる単量体 |
JP2003137855A (ja) * | 2001-08-23 | 2003-05-14 | Nippon Shokubai Co Ltd | 含フッ素芳香族化合物及びその製法 |
WO2003051119A1 (en) * | 2001-12-15 | 2003-06-26 | Bayer Cropscience Limited | New herbicidal compounds and method |
WO2007015567A1 (ja) * | 2005-08-01 | 2007-02-08 | Takeda Pharmaceutical Company Limited | 環状アミン化合物 |
JP2010518067A (ja) * | 2007-02-09 | 2010-05-27 | ファイザー・リミテッド | 抗寄生虫剤 |
JP2011521894A (ja) * | 2008-04-07 | 2011-07-28 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネセント素子用フッ素誘導体 |
JP2012522824A (ja) * | 2009-04-06 | 2012-09-27 | ジョージア・テック・リサーチ・コーポレーション | 新規なホスホン酸表面改質剤を含む電子デバイス |
JP2014135466A (ja) * | 2012-04-09 | 2014-07-24 | Kyushu Univ | 有機発光素子ならびにそれに用いる発光材料および化合物 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4539507A (en) | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
US5151629A (en) | 1991-08-01 | 1992-09-29 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (I) |
DE59510315D1 (de) | 1994-04-07 | 2002-09-19 | Covion Organic Semiconductors | Spiroverbindungen und ihre Verwendung als Elektrolumineszenzmaterialien |
DE19652261A1 (de) | 1996-12-16 | 1998-06-18 | Hoechst Ag | Arylsubstituierte Poly(p-arylenvinylene), Verfahren zur Herstellung und deren Verwendung in Elektroluminszenzbauelementen |
KR101317511B1 (ko) * | 2009-04-30 | 2013-10-15 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 전자 소자 |
JP5773585B2 (ja) * | 2009-06-29 | 2015-09-02 | 日東電工株式会社 | 発光性トリアリール |
EP2536702A4 (en) * | 2010-02-18 | 2013-07-10 | Astrazeneca Ab | NEW CRYSTALLINE FORM OF A CYCLOPROPYLBENZAMIDE DERIVATIVE |
WO2012143079A1 (de) * | 2011-04-18 | 2012-10-26 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
EP2574511B1 (en) | 2011-09-30 | 2016-03-16 | Honda Research Institute Europe GmbH | Analyzing road surfaces |
-
2014
- 2014-02-24 JP JP2016504508A patent/JP6644673B2/ja active Active
- 2014-02-24 CN CN202010441511.2A patent/CN111718281A/zh active Pending
- 2014-02-24 EP EP14706786.2A patent/EP2976322B1/de active Active
- 2014-02-24 KR KR1020157030234A patent/KR102256770B1/ko active IP Right Grant
- 2014-02-24 US US14/778,783 patent/US9718764B2/en active Active
- 2014-02-24 WO PCT/EP2014/000481 patent/WO2014146750A1/de active Application Filing
- 2014-02-24 CN CN201480017494.2A patent/CN105073709A/zh active Pending
-
2017
- 2017-06-27 US US15/634,746 patent/US10407384B2/en active Active
-
2018
- 2018-12-19 JP JP2018237431A patent/JP2019073520A/ja not_active Withdrawn
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3331735A (en) * | 1963-04-01 | 1967-07-18 | Diamond Alkali Co | Halogenated aromatic pesticidal compositions for controlling fungi, bacteria and nematodes |
JPS513974A (ja) * | 1974-06-06 | 1976-01-13 | Diamond Shamrock Corp | Shokubutsuseichosokushinho |
US4556426A (en) * | 1983-06-13 | 1985-12-03 | Tile Council Of America, Inc. | Fungicidal grout composition |
JPS62240655A (ja) * | 1986-04-14 | 1987-10-21 | Sds Biotech Kk | イソフタロニトリル誘導体 |
JPS62294648A (ja) * | 1986-06-13 | 1987-12-22 | Sds Biotech Kk | フツ素含有芳香族ジエ−テル化合物及び該化合物からなる単量体 |
JP2003137855A (ja) * | 2001-08-23 | 2003-05-14 | Nippon Shokubai Co Ltd | 含フッ素芳香族化合物及びその製法 |
WO2003051119A1 (en) * | 2001-12-15 | 2003-06-26 | Bayer Cropscience Limited | New herbicidal compounds and method |
WO2007015567A1 (ja) * | 2005-08-01 | 2007-02-08 | Takeda Pharmaceutical Company Limited | 環状アミン化合物 |
JP2010518067A (ja) * | 2007-02-09 | 2010-05-27 | ファイザー・リミテッド | 抗寄生虫剤 |
JP2011521894A (ja) * | 2008-04-07 | 2011-07-28 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネセント素子用フッ素誘導体 |
JP2012522824A (ja) * | 2009-04-06 | 2012-09-27 | ジョージア・テック・リサーチ・コーポレーション | 新規なホスホン酸表面改質剤を含む電子デバイス |
JP2014135466A (ja) * | 2012-04-09 | 2014-07-24 | Kyushu Univ | 有機発光素子ならびにそれに用いる発光材料および化合物 |
Non-Patent Citations (8)
Title |
---|
BOUYSSOU, PASCAL, ET AL., JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 29(4), JPN6017049288, 1992, pages 895 - 898, ISSN: 0003709242 * |
HEILMAN, WILLIAM P. , ET AL., JOURNAL OF MEDICINAL CHEMISTRY, vol. 21(9), JPN6017049287, 1978, pages 906 - 913, ISSN: 0003959621 * |
HUANG, CHAO, ET AL., BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 23(8), JPN5016004607, 16 February 2013 (2013-02-16), NL, pages 2399 - 2403, ISSN: 0003959620 * |
KORNBLUM, NATHAN, ET AL., TETRAHEDRON, vol. 45(5), JPN6017049290, 1989, pages 1311 - 1322, ISSN: 0003709243 * |
NANDURDIKAR, RAHUL S. , ET AL., BIOORGANIC & MEDICINAL CHEMISTRY, vol. 20(9), JPN5016004609, 2012, GB, pages 3094 - 3099, ISSN: 0003709240 * |
PATCH, RAYMOND J. , ET AL., JOURNAL OF MEDICINAL CHEMISTRY, vol. 54(3), JPN5016004610, 2011, pages 788 - 808, ISSN: 0003709241 * |
UOYAMA, HIROKI, ET AL., NATURE, vol. 492(7428), JPN6017049292, 2012, pages 234 - 238, ISSN: 0003709244 * |
WALLENFELS, K. , ET AL., TETRAHEDRON, vol. 23(3), JPN5016004608, 1 January 1967 (1967-01-01), NL, pages 1353 - 1358, ISSN: 0003709239 * |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018113364A (ja) * | 2017-01-12 | 2018-07-19 | 日本放送協会 | 有機エレクトロルミネッセンス素子 |
WO2018181183A1 (ja) * | 2017-03-28 | 2018-10-04 | キヤノン株式会社 | 光学素子、材料、光学機器及び化合物 |
US11500129B2 (en) | 2017-03-28 | 2022-11-15 | Canon Kabushiki Kaisha | Optical element, material, optical apparatus and compound |
JP7417350B2 (ja) | 2017-03-28 | 2024-01-18 | キヤノン株式会社 | 光学素子、光学材料、光学機器及びトリアリールアミン化合物 |
JP2019006767A (ja) * | 2017-06-21 | 2019-01-17 | 三星ディスプレイ株式會社Samsung Display Co.,Ltd. | ヘテロ環式化合物、及びそれを含んだ有機発光素子 |
US11563183B2 (en) | 2017-06-21 | 2023-01-24 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
JP7304682B2 (ja) | 2017-06-21 | 2023-07-07 | 三星ディスプレイ株式會社 | ヘテロ環式化合物、及びそれを含んだ有機発光素子 |
US11844273B2 (en) | 2017-06-21 | 2023-12-12 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
US11588111B2 (en) | 2017-08-04 | 2023-02-21 | Samsung Display Co., Ltd. | Condensed-cyclic compound and organic light-emitting device including the same |
WO2021066059A1 (ja) * | 2019-10-01 | 2021-04-08 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器 |
Also Published As
Publication number | Publication date |
---|---|
US20170313650A1 (en) | 2017-11-02 |
WO2014146750A1 (de) | 2014-09-25 |
KR20150132873A (ko) | 2015-11-26 |
US20160046563A1 (en) | 2016-02-18 |
CN105073709A (zh) | 2015-11-18 |
US10407384B2 (en) | 2019-09-10 |
US9718764B2 (en) | 2017-08-01 |
JP6644673B2 (ja) | 2020-02-12 |
KR102256770B1 (ko) | 2021-05-26 |
EP2976322B1 (de) | 2019-11-20 |
CN111718281A (zh) | 2020-09-29 |
JP2019073520A (ja) | 2019-05-16 |
EP2976322A1 (de) | 2016-01-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6644673B2 (ja) | 有機エレクトロルミッセンス素子のための材料の調製用の合成構築ブロック | |
CN107619402B (zh) | 具有高效率特性的有机发光元件 | |
JP6239522B2 (ja) | 有機エレクトロルミネッセンス素子 | |
KR102402729B1 (ko) | 유기 전계발광 소자용 재료 | |
JP6165746B2 (ja) | 有機エレクトロルミッセンス素子のための材料 | |
JP6092195B2 (ja) | 有機エレクトロルミネッセンス素子 | |
JP2019536752A (ja) | 二核金属錯体および電子デバイス、特に、前記金属錯体を含んでなる有機エレクトロルミネッセンス素子 | |
JP5833013B2 (ja) | 電子素子のための材料 | |
JP2014513679A (ja) | 有機エレクトロルミネッセンス素子用材料 | |
Butler et al. | Utility of tris (4-bromopyridyl) europium complexes as versatile intermediates in the divergent synthesis of emissive chiral probes | |
KR20240005782A (ko) | 유기 전계 발광 디바이스용 재료 | |
KR20200113220A (ko) | 유기 전계 발광 디바이스용 재료 | |
KR102357223B1 (ko) | 기능성 물질의 합성을 위한 중간체 및 절차 | |
JP2021529207A (ja) | アリールアミンを製造するための方法 | |
KR20240005806A (ko) | 유기 전계발광 디바이스용 재료 | |
JP2020504762A (ja) | 有機エレクトロルミネッセンスデバイス用の材料 | |
WO2021199310A1 (ja) | 芳香族化合物の製造方法 | |
JP2024502093A (ja) | 有機エレクトロルミネッセントデバイスのための材料 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20170222 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20171214 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20180109 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20180404 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20180821 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20181219 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20181227 |
|
A912 | Re-examination (zenchi) completed and case transferred to appeal board |
Free format text: JAPANESE INTERMEDIATE CODE: A912 Effective date: 20190118 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20190918 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20191021 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20191029 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20200108 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6644673 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |