KR20060093800A - 스피로비플루오렌 유도체, 그의 제조 및 그의 용도 - Google Patents
스피로비플루오렌 유도체, 그의 제조 및 그의 용도 Download PDFInfo
- Publication number
- KR20060093800A KR20060093800A KR1020057001890A KR20057001890A KR20060093800A KR 20060093800 A KR20060093800 A KR 20060093800A KR 1020057001890 A KR1020057001890 A KR 1020057001890A KR 20057001890 A KR20057001890 A KR 20057001890A KR 20060093800 A KR20060093800 A KR 20060093800A
- Authority
- KR
- South Korea
- Prior art keywords
- spirobifluorene
- derivatives
- aromatic group
- sbf
- alkyl
- Prior art date
Links
- 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 abstract description 26
- 238000002360 preparation method Methods 0.000 title claims description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 150000005838 radical anions Chemical class 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 19
- -1 aliphatic radical Chemical group 0.000 claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 230000005669 field effect Effects 0.000 claims abstract description 4
- 239000004065 semiconductor Substances 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 24
- 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 claims description 20
- 239000002904 solvent Substances 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 229910052700 potassium Inorganic materials 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 12
- 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 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 238000004377 microelectronic Methods 0.000 claims description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 4
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 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 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 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 3
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 239000003792 electrolyte Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 claims description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- IRKPWADORCEPNA-UHFFFAOYSA-N 9,9'-spirobi[fluorene]-2-carbonyl chloride Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=C(C(=O)Cl)C=C12 IRKPWADORCEPNA-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000005868 electrolysis reaction Methods 0.000 claims 1
- 238000005401 electroluminescence Methods 0.000 abstract description 4
- 238000005442 molecular electronic Methods 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 90
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 34
- 238000003756 stirring Methods 0.000 description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 239000003480 eluent Substances 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 15
- 239000008346 aqueous phase Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- PMDGDMHDPNFIPW-UHFFFAOYSA-N phenyl(9,9'-spirobi[fluorene]-2-yl)methanone Chemical compound C=1C=C2C3=CC=CC=C3C3(C4=CC=CC=C4C4=CC=CC=C43)C2=CC=1C(=O)C1=CC=CC=C1 PMDGDMHDPNFIPW-UHFFFAOYSA-N 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 239000008151 electrolyte solution Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- PHYWAIOCEHDTHP-UHFFFAOYSA-N [2'-(4-fluorobenzoyl)-9,9'-spirobi[fluorene]-2-yl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(C=2C(=CC=CC=2)C23C4=CC(=CC=C4C4=CC=CC=C43)C(=O)C=3C=CC(F)=CC=3)C2=C1 PHYWAIOCEHDTHP-UHFFFAOYSA-N 0.000 description 4
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
- 229910021397 glassy carbon Inorganic materials 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- WGHUNMFFLAMBJD-UHFFFAOYSA-M tetraethylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CC[N+](CC)(CC)CC WGHUNMFFLAMBJD-UHFFFAOYSA-M 0.000 description 4
- FVLANAMJWVQMQQ-UHFFFAOYSA-N 1-(2'-acetyl-9,9'-spirobi[fluorene]-2-yl)ethanone Chemical compound C12=CC=CC=C2C2=CC=C(C(C)=O)C=C2C21C1=CC=CC=C1C1=CC=C(C(=O)C)C=C12 FVLANAMJWVQMQQ-UHFFFAOYSA-N 0.000 description 3
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- IUPUUHSDFMCJIP-UHFFFAOYSA-N [2'-(thiophene-2-carbonyl)-9,9'-spirobi[fluorene]-2-yl]-thiophen-2-ylmethanone Chemical compound C=1C=C2C3=CC=CC=C3C3(C4=CC(=CC=C4C4=CC=CC=C43)C(=O)C=3SC=CC=3)C2=CC=1C(=O)C1=CC=CS1 IUPUUHSDFMCJIP-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical compound Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 3
- 238000002848 electrochemical method Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- MYHOHFDYWMPGJY-UHFFFAOYSA-N pentafluorobenzoyl chloride Chemical compound FC1=C(F)C(F)=C(C(Cl)=O)C(F)=C1F MYHOHFDYWMPGJY-UHFFFAOYSA-N 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 3
- AXIHLUSDNBGLCM-UHFFFAOYSA-N (2'-benzoyl-9,9'-spirobi[fluorene]-2-yl)-phenylmethanone Chemical compound C=1C=C2C3=CC=CC=C3C3(C4=CC(=CC=C4C4=CC=CC=C43)C(=O)C=3C=CC=CC=3)C2=CC=1C(=O)C1=CC=CC=C1 AXIHLUSDNBGLCM-UHFFFAOYSA-N 0.000 description 2
- PNDPGGVYLHLWGT-UHFFFAOYSA-N (4-tert-butylphenyl)-(9,9'-spirobi[fluorene]-2-yl)methanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)C1=CC=C(C=2C(=CC=CC=2)C23C4=CC=CC=C4C4=CC=CC=C43)C2=C1 PNDPGGVYLHLWGT-UHFFFAOYSA-N 0.000 description 2
- LBDBFEJSQZIUOX-UHFFFAOYSA-N 2-(furan-2-yl)-2-oxoacetyl chloride Chemical compound ClC(=O)C(=O)C1=CC=CO1 LBDBFEJSQZIUOX-UHFFFAOYSA-N 0.000 description 2
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229940075397 calomel Drugs 0.000 description 2
- 238000002484 cyclic voltammetry Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- UFUHDMPCBVZHDW-UHFFFAOYSA-N furan-2-yl(9,9'-spirobi[fluorene]-1-yl)methanone Chemical compound C=1C=CC=2C3=CC=CC=C3C3(C4=CC=CC=C4C4=CC=CC=C43)C=2C=1C(=O)C1=CC=CO1 UFUHDMPCBVZHDW-UHFFFAOYSA-N 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000005297 pyrex Substances 0.000 description 2
- 150000003413 spiro compounds Chemical class 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003115 supporting electrolyte Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RZWLQRMBWWMZOU-UHFFFAOYSA-N (4-fluorophenyl)-(9,9'-spirobi[fluorene]-2-yl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(C=2C(=CC=CC=2)C23C4=CC=CC=C4C4=CC=CC=C43)C2=C1 RZWLQRMBWWMZOU-UHFFFAOYSA-N 0.000 description 1
- CXNPSSFFBVGGRH-UHFFFAOYSA-N (4-methoxyphenyl)-(9,9'-spirobi[fluorene]-2-yl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(C=2C(=CC=CC=2)C23C4=CC=CC=C4C4=CC=CC=C43)C2=C1 CXNPSSFFBVGGRH-UHFFFAOYSA-N 0.000 description 1
- UWYLNIDYNYDTOX-UHFFFAOYSA-N (4-nitrophenyl)-(9,9'-spirobi[fluorene]-2-yl)methanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)C1=CC=C(C=2C(=CC=CC=2)C23C4=CC=CC=C4C4=CC=CC=C43)C2=C1 UWYLNIDYNYDTOX-UHFFFAOYSA-N 0.000 description 1
- MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical class CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 1
- WNLMYNASWOULQY-UHFFFAOYSA-N 4-tert-butylbenzoyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)C=C1 WNLMYNASWOULQY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BLOJUVWYFKTBHL-UHFFFAOYSA-N C12(C(=CC=C3C4=CC=CC=C4C=C13)C(=O)O)C(=CC=C1C3=CC=CC=C3C=C12)C(=O)O Chemical compound C12(C(=CC=C3C4=CC=CC=C4C=C13)C(=O)O)C(=CC=C1C3=CC=CC=C3C=C12)C(=O)O BLOJUVWYFKTBHL-UHFFFAOYSA-N 0.000 description 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- SPMMUDILVUJNPH-UHFFFAOYSA-N [2'-(4-tert-butylbenzoyl)-9,9'-spirobi[fluorene]-2-yl]-(4-tert-butylphenyl)methanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)C1=CC=C(C=2C(=CC=CC=2)C23C4=CC(=CC=C4C4=CC=CC=C43)C(=O)C=3C=CC(=CC=3)C(C)(C)C)C2=C1 SPMMUDILVUJNPH-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- NENBKFYWWJFYKI-UHFFFAOYSA-N furan-2-yl(9,9'-spirobi[fluorene]-2-yl)methanone Chemical compound C=1C=C2C3=CC=CC=C3C3(C4=CC=CC=C4C4=CC=CC=C43)C2=CC=1C(=O)C1=CC=CO1 NENBKFYWWJFYKI-UHFFFAOYSA-N 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 1
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
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Abstract
Description
모노 유도체에 대한 표준 전위 | |
생성물 | E°(V vs SCE) |
2-(4-니트로벤조일)-9,9'-스피로비플루오렌 | -0.81 |
2-(펜타플루오로)-벤조일-9,9'-스피로비플루오렌 | -1.36 |
2-(2-푸로일)-9,9'-스피로비플루오렌 | -1.49 |
2-(4-플루오로벤조일)-9,9'-스피로비플루오렌 | -1.60 |
2-벤조일-9,9'-스피로비플루오렌 | -1.62 |
2-(4-메톡시벤조일)-9,9'-스피로비플루오렌 | -1.64 |
2-(4-tert-부틸벤조일)-9,9'-스피로비플루오렌 | -1.69 |
디-유도체에 대한 표준 전위 | |
생성물 | E°(V vs SCE) |
2,2'-디-(펜타플루오로)-벤조일-9,9'-스피로비플루오렌 | -1.39 |
2,2'-디-(2-티에노일)-9,9'-스피로비플루오렌 | -1.47 |
2,2'-디-(4-플루오로벤조일)-9,9'-스피로비플루오렌 | -1.57 |
2,2'-디-(4-tert-부틸벤조일)-9,9'-스피로비플루오렌 | -1.63 |
2,2'-디벤조일-9,9'-스피로비플루오렌 | -1.65 |
Claims (27)
- 제 1 항에 있어서, A가, 방향족기, 헤테로원자 함유 방향족기, 축합 방향족기, 헤테로원자 함유 축합 방향족기 및 대응하는 유도체들 중에서 선택되는 스피로비플루오렌 유도체 및 대응하는 라디칼 음이온.
- 제 1 항에 있어서, A 가 하기 유도체의 군에서 선택되는 스피로비플루오렌 유도체 및 대응하는 라디칼 음이온: 페닐, 비페닐, 1-나프틸, 2-나프틸, 2-티에닐, 2-푸릴, 2-피롤릴, 3-티에닐, 3-푸릴, 3-피롤릴, 9-안트릴, 비페닐레닐, 페릴레닐, 풀레레닐 및 대응하는 유도체들.
- 제 1 항에 있어서, R 이 선형, 분지형 또는 고리형 지방족 C1-Cn 이고, n 은 ≥0 인 양의 정수, 바람직하게는 C1-C18, 더 바람직하게는 C1-C6인 스피로비플루오렌 유도체 및 대응하는 라디칼 음이온.
- 제 1 항에 있어서, A 가 하나 이상의 R' 기로 치환되며, R' 는 하기의 군에서 선택되는 스피로비플루오렌 유도체 및 대응하는 라디칼 음이온: 할로겐, 트리플루오로메틸, 히드록실, -SH, -SC[C1-6(알킬)], 알콕시, 니트로, 시아노, -COOH, -COOC[C1-4(알킬)], -NH2, -NC[C1-4(알킬)]2, 벤질, 벤조일.
- 제 6 항 내지 제 9 항 중 어느 한 항에 있어서, A 가 방향족기, 헤테로원자 함유 방향족기, 축합 방향족기, 헤테로원자 함유 축합 방향족기 및 대응하는 유도체들 중에서 선택되는 스피로비플루오렌 유도체 및 대응하는 라디칼 음이온.
- 제 6 항 내지 제 9 항 중 어느 한 항에 있어서, A 가 하기의 군에서 선택되는 스피로비플루오렌 유도체 및 대응하는 라디칼 음이온: 페닐, 비페닐, 1-나프틸, 2-나프틸, 2-티에닐, 2-푸릴, 2-피롤릴, 3-티에닐, 3-푸릴, 3-피롤릴, 9-안트릴, 비페닐레닐, 페릴레닐, 풀레레닐, 및 대응하는 유도체.
- 제 1 항에 있어서, L=M=N=H 이고, 위치 2 의 K=A-C=O (여기서, A=페닐) 이며, R=H 인 스피로비플루오렌 유도체 및 대응하는 라디칼 음이온.
- 제 1 항에 있어서, L=N=H 이고, 위치 2 및 2' 의 K 및 M 이 A-C=O (여기서, A=페닐) 이며, R=H 인 스피로비플루오렌 유도체 및 대응하는 라디칼 음이온.
- 제 1 항에 있어서, L=N=H 이고, 위치 2 및 7' 의 K 및 M 이 A-C=O (여기서, A=페닐) 이며, R=H 인 스피로비플루오렌 유도체 및 대응하는 라디칼 음이온.
- 제 1 항에 있어서, L=M=N=H 이고, 위치 2 의 K 가 A-C=O (여기서, A=페닐) 이며, R=p-tert-Bu 인 스피로비플루오렌 유도체 및 대응하는 라디칼 음이온.
- 제 1 항에 있어서, L=N=H 이고, 위치 2 및 2' 의 K 및 M 이 A-C=O (여기서, A=페닐) 이며, R=p-tert-Bu 인 스피로비플루오렌 유도체 및 대응 음이온성 라디칼.
- 제 1 항에 있어서, L=M=H 이고, 위치 2 및 7' 의 K 및 N 이 A-C=O (여기서, A=페닐) 이며, R=p-tert-Bu 인 스피로비플루오렌 유도체 및 대응 라디칼 음이온.
- 제 1 항 내지 제 17 항 중 어느 한 항에 있어서, 거울상 이성질체의 혼합물인 스피로비플루오렌 유도체 및 대응하는 라디칼 음이온.
- 제 1 항 내지 제 17 항 중 어느 한 항에 있어서, 광학적으로 순수한 형태인 스피로비플루오렌 유도체 및 대응하는 라디칼 음이온.
- 하기 단계를 포함하는, 제 1 항에 따른 스피로비플루오렌 유도체의 제조 방법:비관능화 SBF 를 출발 생성물 (화학식 I) 로 사용하고,이를 반응 온도 10℃ 내지 환류 온도에서, 바람직하게는 CH2Cl2 및 CS2 로부터 선택되는 용매, 특히 바람직하게는 CH2Cl2 중, 바람직하게는 AlCl3, AlBr3, FeCl3 중에서 선택되는 루이스산, 특히 바람직하게는 AlCl3 의 존재 하에, 화합물 A-C=OCl (이때, A = 방향족기임) 에 첨가함.
- 하기를 포함하는, 제 1 항에 따른 스피로비플루오렌 유도체의 제조 방법:산 염화물 SBF(COCl)x (이때, x 는 1 이상의 양의 정수이며, SBF 상에서 수득되는 치환기의 수와 같음) 로서 관능화된 SBF 를 중간체로 사용하고;이어서 상기 산 염화물을 A-H (여기서, A = 방향족기임) 와 조합함 (상기 산 염화물 중간체는 대응하는 아세틸 유도체 SBF(COCH3)x 로부터 수득되는, SBF 의 대응 카르복실산인 SBF(COOH)x 로부터 제조되며, x 는 두 경우 모두 상술된 의미를 가짐).
- 9,9'-스피로비[9H-플루오렌]-2-카르보닐 클로라이드.
- 9,9'-스피로비[9H-플루오렌]-2,2',7-트리카르보닐 트리클로라이드.
- 9,9'-스피로비[9H-플루오렌]-2,2',7-7'-테트라카르보닐 테트라클로라이드.
- 제 1 항 내지 제 24 항 중 어느 한 항에 따른 SBF 의 유도체에 대응하는 라디칼 음이온의 전기화학적 제조 방법에 있어서, 라디칼 음이온으로 전환될 상기 유도체를 0.1 M 내지 0.1 mM, 바람직하게는 0.01 M 내지 0.5 mM, 특히 바람직하게는 약 1 mM 의 농도로 역시 무수물인 지지 전해질을 함유하는 무수 비양성자성 용매에 첨가하여 지지 전해질 농도 1 M 내지 0.01 M, 바람직하게는 0.2 M 내지 0.05 M, 특히 바람직하게는 약 0.1 M 을 수득한 후, 혼합물을 전기분해 전지내에 위치시키고 전극 사이에 d.d.p. 를 적용하여 목적하는 라디칼 음이온을 수득하는 것을 특징으로 하는 방법.
- 전자 장치, 특히 전자발광용 시스템, 분자-기재 컴퓨터 시스템, OLED, 분자 스위칭 성분, 비선형 광학용 성분, 분자-기재 컴퓨터 시스템, 전계-효과 트랜지스터, 부성저항 (negative differential resistance, NDR) 을 갖는 반도체에 있어서, 제 1 항 내지 제 24 항 중 어느 한 항에 따른 하나 이상의 화합물을 함유하는 필름 또는 코팅이 한층 이상 표면에 제공되는 요소를 포함하는 시스템.
- 극소 전자공학용 성분, 특히 전자발광용 시스템, 분자-기재 컴퓨터 시스템, OLED, 분자 스위칭 성분, 비선형 광학용 성분, 분자-기재 컴퓨터 시스템, 전계-효과 트랜지스터, 및 부성저항 (negative differential resistance, NDR) 을 갖는 반도체에서의, 제 1 항 내지 제 24 항 중 어느 한 항에 따른 화합물의 용도.
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GB8623510D0 (en) * | 1986-09-30 | 1986-11-05 | Raychem Ltd | Aryl carbonyl compounds |
DE59510315D1 (de) * | 1994-04-07 | 2002-09-19 | Covion Organic Semiconductors | Spiroverbindungen und ihre Verwendung als Elektrolumineszenzmaterialien |
EP0863931A2 (de) * | 1995-12-01 | 1998-09-16 | Ciba SC Holding AG | Poly(9,9'-spirobisfluorene), deren herstellung und deren verwendung |
DE19711568A1 (de) * | 1997-03-20 | 1998-10-01 | Hoechst Ag | Spiroverbindungen und deren Verwendung |
JPH1154284A (ja) * | 1997-08-04 | 1999-02-26 | Canon Inc | 電界発光素子 |
KR100610126B1 (ko) * | 1998-02-04 | 2006-08-09 | 메르크 파텐트 게엠베하 | 레이저 염료로서의 스피로 화합물의 용도 |
DE19808936A1 (de) * | 1998-03-03 | 1999-09-16 | Aventis Res & Tech Gmbh & Co | Photodetektor und seine Verwendung |
ITRM20020411A1 (it) * | 2002-08-01 | 2004-02-02 | Univ Roma La Sapienza | Derivati dello spirobifluorene, loro preparazione e loro uso. |
EP1618170A2 (de) * | 2003-04-15 | 2006-01-25 | Covion Organic Semiconductors GmbH | Mischungen von organischen zur emission befähigten halbleitern und matrixmaterialien, deren verwendung und elektronikbauteile enthaltend diese mischungen |
DE10357315A1 (de) * | 2003-12-05 | 2005-07-07 | Covion Organic Semiconductors Gmbh | Organisches Elektrolumineszenzelement |
-
2002
- 2002-08-01 IT IT000411A patent/ITRM20020411A1/it unknown
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2003
- 2003-07-31 US US10/523,101 patent/US7557249B2/en not_active Expired - Fee Related
- 2003-07-31 DE DE60336907T patent/DE60336907D1/de not_active Expired - Lifetime
- 2003-07-31 KR KR1020057001890A patent/KR100969179B1/ko active IP Right Grant
- 2003-07-31 AU AU2003260342A patent/AU2003260342A1/en not_active Abandoned
- 2003-07-31 JP JP2004525396A patent/JP4572113B2/ja not_active Expired - Fee Related
- 2003-07-31 EP EP03766376A patent/EP1534661B1/en not_active Expired - Lifetime
- 2003-07-31 CN CNB038207818A patent/CN100338022C/zh not_active Expired - Fee Related
- 2003-07-31 WO PCT/EP2003/008465 patent/WO2004013080A1/en active Application Filing
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DE60336907D1 (de) | 2011-06-09 |
AU2003260342A1 (en) | 2004-02-23 |
EP1534661B1 (en) | 2011-04-27 |
CN100338022C (zh) | 2007-09-19 |
KR100969179B1 (ko) | 2010-07-08 |
ITRM20020411A1 (it) | 2004-02-02 |
US8188462B2 (en) | 2012-05-29 |
EP1534661A1 (en) | 2005-06-01 |
CN1678561A (zh) | 2005-10-05 |
US20090302274A1 (en) | 2009-12-10 |
ITRM20020411A0 (it) | 2002-08-01 |
JP4572113B2 (ja) | 2010-10-27 |
WO2004013080A1 (en) | 2004-02-12 |
US20060006365A1 (en) | 2006-01-12 |
JP2005538999A (ja) | 2005-12-22 |
US7557249B2 (en) | 2009-07-07 |
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