TWI388564B - 經取代苯基乙炔基金-含氮雜環碳烯錯合物 - Google Patents
經取代苯基乙炔基金-含氮雜環碳烯錯合物 Download PDFInfo
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- TWI388564B TWI388564B TW096118660A TW96118660A TWI388564B TW I388564 B TWI388564 B TW I388564B TW 096118660 A TW096118660 A TW 096118660A TW 96118660 A TW96118660 A TW 96118660A TW I388564 B TWI388564 B TW I388564B
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- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 title claims description 35
- 125000000623 heterocyclic group Chemical group 0.000 title claims description 31
- ABDXFQAMNQWLPT-UHFFFAOYSA-N [N].[Au]C#CC1=CC=CC=C1 Chemical compound [N].[Au]C#CC1=CC=CC=C1 ABDXFQAMNQWLPT-UHFFFAOYSA-N 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 100
- -1 2,6-diisopropylphenyl group Chemical group 0.000 claims description 59
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical class C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 150000001721 carbon Chemical group 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 239000003446 ligand Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 11
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 125000005110 aryl thio group Chemical group 0.000 claims description 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000005592 polycycloalkyl group Polymers 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 150000001345 alkine derivatives Chemical class 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 117
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 105
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 68
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 68
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 47
- 239000000203 mixture Substances 0.000 description 46
- 239000011541 reaction mixture Substances 0.000 description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 239000010931 gold Substances 0.000 description 35
- 229910052786 argon Inorganic materials 0.000 description 34
- 238000005160 1H NMR spectroscopy Methods 0.000 description 33
- 238000003786 synthesis reaction Methods 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 30
- 239000007787 solid Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 239000007795 chemical reaction product Substances 0.000 description 23
- 235000019439 ethyl acetate Nutrition 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
- 238000004440 column chromatography Methods 0.000 description 22
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 239000000460 chlorine Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 17
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 14
- 238000000921 elemental analysis Methods 0.000 description 14
- 238000004020 luminiscence type Methods 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- 238000002076 thermal analysis method Methods 0.000 description 11
- 238000001035 drying Methods 0.000 description 10
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- 235000019270 ammonium chloride Nutrition 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 8
- 229910052737 gold Inorganic materials 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- AVJBQMXODCVJCJ-UHFFFAOYSA-M 1,3-bis[2,6-di(propan-2-yl)phenyl]imidazol-1-ium;chloride Chemical compound [Cl-].CC(C)C1=CC=CC(C(C)C)=C1N1C=[N+](C=2C(=CC=CC=2C(C)C)C(C)C)C=C1 AVJBQMXODCVJCJ-UHFFFAOYSA-M 0.000 description 6
- PHPIMLZTBYCDSX-UHFFFAOYSA-N 3-ethynylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C#C)=C1 PHPIMLZTBYCDSX-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 6
- 238000001291 vacuum drying Methods 0.000 description 6
- MPONAPFARZGDTH-UHFFFAOYSA-N Cl.OS(O)=O Chemical compound Cl.OS(O)=O MPONAPFARZGDTH-UHFFFAOYSA-N 0.000 description 5
- 238000005401 electroluminescence Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- BPPGPFOTTDXLDS-UHFFFAOYSA-N 1,3-bis[2,6-di(propan-2-yl)phenyl]-2h-imidazole;hydrochloride Chemical compound [Cl-].CC(C)C1=CC=CC(C(C)C)=C1N1C=C[NH+](C=2C(=CC=CC=2C(C)C)C(C)C)C1 BPPGPFOTTDXLDS-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- TVPNFSJRTAQQOQ-UHFFFAOYSA-N (2-ethynylphenyl)-phenylmethanone Chemical compound C=1C=CC=C(C#C)C=1C(=O)C1=CC=CC=C1 TVPNFSJRTAQQOQ-UHFFFAOYSA-N 0.000 description 3
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 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 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- KYABTUSRPCQRFU-UHFFFAOYSA-N n,n-diethyl-3-ethynylbenzamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C#C)=C1 KYABTUSRPCQRFU-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- DKQONZPFABJCNX-UHFFFAOYSA-N s-methyl 3-ethynylbenzenecarbothioate Chemical compound CSC(=O)C1=CC=CC(C#C)=C1 DKQONZPFABJCNX-UHFFFAOYSA-N 0.000 description 3
- VRDACQUDHPNIJM-UHFFFAOYSA-N s-phenyl 3-ethynylbenzenecarbothioate Chemical compound C=1C=CC(C#C)=CC=1C(=O)SC1=CC=CC=C1 VRDACQUDHPNIJM-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- WNMIRCGBPKWNBR-UHFFFAOYSA-N (3-ethynylphenyl)-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CC(C#C)=C1 WNMIRCGBPKWNBR-UHFFFAOYSA-N 0.000 description 2
- NICMXQZRHOKNPM-UHFFFAOYSA-N (3-ethynylphenyl)-phenylmethanone Chemical compound C=1C=CC(C#C)=CC=1C(=O)C1=CC=CC=C1 NICMXQZRHOKNPM-UHFFFAOYSA-N 0.000 description 2
- QJIMTLTYXBDJFC-UHFFFAOYSA-N (4-methylphenyl)-diphenylphosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJIMTLTYXBDJFC-UHFFFAOYSA-N 0.000 description 2
- LHNRHYOMDUJLLM-UHFFFAOYSA-N 1-hexylsulfanylhexane Chemical compound CCCCCCSCCCCCC LHNRHYOMDUJLLM-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical group CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- SLKUPHOLMBNXIM-UHFFFAOYSA-N 3-ethynyl-n,n-diphenylbenzamide Chemical compound C=1C=CC(C#C)=CC=1C(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 SLKUPHOLMBNXIM-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 241000208340 Araliaceae Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 2
- 235000003140 Panax quinquefolius Nutrition 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- IBIYMKGFWFEPPB-UHFFFAOYSA-N [Au].C(C)N(C(=O)C=1C=C(C=CC1)C#CC1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1)CC Chemical compound [Au].C(C)N(C(=O)C=1C=C(C=CC1)C#CC1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1)CC IBIYMKGFWFEPPB-UHFFFAOYSA-N 0.000 description 2
- MKHLCHSQBLGBTR-UHFFFAOYSA-N [Au].C1(=CC=CC=C1)N(C(=O)C=1C=C(C=CC1)C#CC1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [Au].C1(=CC=CC=C1)N(C(=O)C=1C=C(C=CC1)C#CC1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 MKHLCHSQBLGBTR-UHFFFAOYSA-N 0.000 description 2
- SIMJNMXPARBIJO-UHFFFAOYSA-N [Au].O(C1=CC=CC=C1)C(=O)C=1C=C(C=CC1)C#CC1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [Au].O(C1=CC=CC=C1)C(=O)C=1C=C(C=CC1)C#CC1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 SIMJNMXPARBIJO-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical class BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000005266 diarylamine group Chemical group 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical group CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- DIZFWJVCPSJKGW-UHFFFAOYSA-N ethyl 3-ethynylbenzoate Chemical compound CCOC(=O)C1=CC=CC(C#C)=C1 DIZFWJVCPSJKGW-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 235000008434 ginseng Nutrition 0.000 description 2
- VENHFCZBHVZHMO-UHFFFAOYSA-N gold;triphenylphosphane Chemical compound [Au].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VENHFCZBHVZHMO-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000005446 heptyloxy 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])O* 0.000 description 2
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- CMLWFCUAXGSMBB-UHFFFAOYSA-N tris(2,6-dimethoxyphenyl)phosphane Chemical compound COC1=CC=CC(OC)=C1P(C=1C(=CC=CC=1OC)OC)C1=C(OC)C=CC=C1OC CMLWFCUAXGSMBB-UHFFFAOYSA-N 0.000 description 1
- IIOSDXGZLBPOHD-UHFFFAOYSA-N tris(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC IIOSDXGZLBPOHD-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- DAGQYUCAQQEEJD-UHFFFAOYSA-N tris(2-methylpropyl)phosphane Chemical compound CC(C)CP(CC(C)C)CC(C)C DAGQYUCAQQEEJD-UHFFFAOYSA-N 0.000 description 1
- CUTRINLXFPIWQB-UHFFFAOYSA-N tris(3-fluorophenyl)phosphane Chemical compound FC1=CC=CC(P(C=2C=C(F)C=CC=2)C=2C=C(F)C=CC=2)=C1 CUTRINLXFPIWQB-UHFFFAOYSA-N 0.000 description 1
- CCXTYQMZVYIQRP-UHFFFAOYSA-N tris(3-methoxyphenyl)phosphane Chemical compound COC1=CC=CC(P(C=2C=C(OC)C=CC=2)C=2C=C(OC)C=CC=2)=C1 CCXTYQMZVYIQRP-UHFFFAOYSA-N 0.000 description 1
- LFNXCUNDYSYVJY-UHFFFAOYSA-N tris(3-methylphenyl)phosphane Chemical compound CC1=CC=CC(P(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 LFNXCUNDYSYVJY-UHFFFAOYSA-N 0.000 description 1
- IQKSLJOIKWOGIZ-UHFFFAOYSA-N tris(4-chlorophenyl)phosphane Chemical compound C1=CC(Cl)=CC=C1P(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 IQKSLJOIKWOGIZ-UHFFFAOYSA-N 0.000 description 1
- GEPJPYNDFSOARB-UHFFFAOYSA-N tris(4-fluorophenyl)phosphane Chemical compound C1=CC(F)=CC=C1P(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 GEPJPYNDFSOARB-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- GNFABDZKXNKQKN-UHFFFAOYSA-N tris(prop-2-enyl)phosphane Chemical compound C=CCP(CC=C)CC=C GNFABDZKXNKQKN-UHFFFAOYSA-N 0.000 description 1
- PXYCJKZSCDFXLR-UHFFFAOYSA-N tris[4-(trifluoromethyl)phenyl]phosphane Chemical compound C1=CC(C(F)(F)F)=CC=C1P(C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 PXYCJKZSCDFXLR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
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Description
本發明係有關作為電場發光元件(有機電激發光(electroluminescence)元件)用發光材料等有用之經取代苯基乙炔基金-含氮雜環碳烯錯合物。
有機電激發光元件近年來作為高性能平面彩色顯示器用顯示裝置受注目,發光材料主要利用從發光分子之激發單重態(excited singlet state)發光之螢光材料,為了達到更高效率,而盛大進行開發利用從激發三重態發光之磷光發光材料。然而,本發明之經取代苯基乙炔基金-含氮雜環碳烯錯合物則完全尚未為人所知。
本發明之課題為提供具有實現全彩顯示器不可缺之460nm以下藍色區帶之發光,具有可忍受施加電壓時產生之焦耳熱200℃以上之高融點,作為有機電激發光元件用發光材料等有用之非離子性化合物。
該種課題可由通式(1)或(2)表示之經取代苯基乙炔基金-含氮雜環碳烯錯合物解決。
依本發明可提供作為有機電激發光元件用發光材料等有用之經取代苯基乙炔基金-含氮雜環碳烯錯合物。
本發明之經取代苯基乙炔基金-含氮雜環碳烯錯合物以上述通式(1)或(2)表示。於該通式(1)或(2),L表示含氮雜環碳烯配位基。X表示烷基、環烷基、芳基、芳烷基、雜環基、烷氧基、芳氧基、烷基硫基、芳基硫基或取代胺基。
上述烷基較好為碳原子數1至10之烷基,可列舉例如甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基等。以碳原子數1至6之烷基較佳。此等取代基亦包含其異構物。
上述環烷基較好為碳原子數3至12之環烷基,可列舉例如環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基、環十一碳基、環十二碳基等。
上述芳基較好為碳原子數6至18之芳基,可列舉例如苯基、甲苯基、二甲苯基、聯苯基、茚基(indenyl)、萘基、二甲基萘基、蒽基、菲基(phenanthryl)、茀基(fluorenyl)、芘基(pyrenyl)、屈基(chrysenyl)、丁省基(naphthacenyl)等。以碳子數6至14之芳基較佳。此等取代基亦包含其異構物。
上述芳烷基較好為碳原子數7至20之芳烷基,可列舉例如苯甲基、苯乙基、萘甲基、茚基甲基、聯苯基甲基等。
上述雜環基較好為由含有選自N、O或S之至少1個雜原子之3至10員環組成之飽和或不飽和環式基,可列舉例如吡咯基、呋喃基、噻吩基(thienyl)、吲哚基(indolyl)、苯并呋喃基(benzofuranyl)、苯并噻吩基(benzothiophenyl)、吡啶基、吡基、嘧啶基、嗒基、喹啉基、異喹啉基、喹唑啉基(quinazolinyl)、喹啉基(quinoxalinyl)等。
上述烷氧基較好為碳原子數1至10之烷氧基,可列舉例如甲氧基、乙氧基、丙氧基、丁氧基、戊氧基、己氧基、庚氧基、辛氧基、壬氧基、癸氧基等。以碳原子數1至6之烷氧基較佳。此等取代基亦包含其異構物。
上述芳氧基較好為碳原子數6至14之芳氧基,可列舉例如苯氧基、甲苯氧基、二甲苯氧基、萘氧基等。此等取代基亦包含其異構物。
上述烷基硫基較好為碳原子數1至6之烷基硫基,可列舉例如甲基硫基、乙基硫基、丙基硫基、丁基硫基、戊基硫基、己基硫基等。此等取代基亦包含其異構物。
上述芳基硫基較好為碳原子數6至14之芳基硫基,可列舉例如苯基硫基、甲苯基硫基、二甲苯基硫基、萘基硫基等。此等取代基亦包含其異構物。
上述取代胺基較好為經選自碳原子數1至6之烷基、碳原子數6至14之芳基或碳原子數7至20之芳烷基之1或2個基取代之胺基。可列舉例如甲胺基、乙胺基、丙胺基、丁胺基等碳原子數1至6之烷胺基,二甲胺基、甲基乙胺基、二乙胺基、二丙胺基等經相同或不同之2個碳原子數1至6之烷基取代之二烷胺基,苯胺基、甲苯胺基、二甲苯胺基、萘胺基等碳原子數6至14之芳胺基,二苯胺基、二(甲苯)胺基、二(二甲苯)胺基等經相同或不同之2個碳原子數6至14之芳基取代之二芳胺基,苯甲胺基、苯乙胺基等碳原子數7至20之芳烷胺基或二苯甲胺基等經相同或不同之2個碳原子數7至20之芳烷基取代之二芳烷基胺基。此等取代基亦包含其異構物。
X之碳原子上一個或複數個氫原子可獨立地經鹵素原子、烷基、環烷基、烯基、芳基、芳烷基、烷氧基、芳氧基、烷基硫基、芳基硫基或經取代胺基所取代。
上述鹵素原子可列舉氟原子、氯原子、溴原子、碘原子。
上述烷基較好為碳原子數1至20,更好為1至12之烷基,可列舉例如甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一碳基、十二碳基等。以碳原子數1至6之烷基較佳。此等取代基亦包含其異構物。
上述環烷基較好為碳原子數3至7之環烷基,可列舉例如環丙基、環丁基、環戊基、環己基、環庚基等。
上述烯基較好為碳原子數2至20,更好為2至12之烯基,可列舉例如乙烯基、丙烯基、丁烯基、戊烯基、己烯基、庚烯基、辛烯基、壬烯基、癸烯基、十一碳烯基、十二碳烯基等。此等取代基亦包含其異構物。
上述芳基較好為碳原子數6至20,更好為6至16之芳基,可列舉例如苯基、甲苯基、二甲苯基、萘基、二甲基萘基、蒽基、菲基、茀基、芘基等。此等取代基亦包含其異構物。
上述芳烷基較好為碳原子數7至20之芳烷基,可列舉例如苯甲基、苯乙基、萘甲基、茚基甲基、聯苯基甲基等。
上述烷氧基較好為碳原子數1至10之烷氧基,可列舉例如甲氧基、乙氧基、丙氧基、丁氧基、戊氧基、己氧基、庚氧基、辛氧基、壬氧基、癸氧基等。此等取代基亦包含其異構物。
上述芳氧基較好為碳原子數6至14之芳氧基,可列舉例如苯氧基、甲苯氧基、二甲苯氧基、萘氧基等。此等取代基亦包含其異構物。
上述烷基硫基較好為碳原子數1至6之烷基硫基,可列舉例如甲基硫基、乙基硫基、丙基硫基、丁基硫基、戊基硫基、己基硫基。此等取代基亦包含其異構物。
上述芳基硫基較好為碳原子數6至14之芳基硫基,可列舉例如苯基硫基、甲苯基硫基、二甲苯基硫基、萘基硫基等。此等取代基亦包含其異構物。
上述取代胺基較好為經選自碳原子數1至6之烷基、碳原子數6至14之芳基或碳原子數7至20之芳烷基之1或2個基取代之胺基。可列舉例如甲胺基、乙胺基、丙胺基、丁胺基等碳原子數1至6之烷胺基,二甲胺基、甲基乙基胺基、二乙胺基、二丙胺基等經相同或不同之2個碳原子數1至6之烷基取代之二烷胺基,苯胺基、甲苯基胺基、二甲苯基胺基、萘胺基等碳原子數6至14之芳胺基,二苯胺基、二(甲苯基)胺基、二(二甲苯基)胺基等相同或不同之2個碳原子數6至14之芳基取代之二芳胺基,苯甲胺基、苯乙胺基等碳原子數7至20之芳烷基胺基或二苯甲胺基等相同或不同之2個碳原子數7至20之芳烷基取代之二芳烷基胺基。此等取代基亦包含其異構物。
X之碳原子上複數個氫原子經烷基、烯基、芳基、芳烷基、烷氧基、芳氧基或取代胺基取代時,鄰接之基之間可鍵結形成環。
上述鄰接之基之間鍵結形成環時之環可列舉例如環戊烯環、環己烯環、環庚烯環、苯環、萘環、四氫呋喃環、苯并吡喃環、N-甲基吡咯啶環、N-甲基哌啶環等。
此等中,X為選自碳原子數1至6之烷基、碳原子數6至14之芳基、碳原子數1至6之烷氧基、碳原子數6至14之芳氧基、碳原子數1至6之烷基硫基、碳原子數6至14之芳基硫基、經相同或不同之2個碳原子數1至6之烷基取代之二烷胺基、經相同或不同之2個碳原子數6至14之芳基取代之二芳胺基,X之碳原子上一個或複數個氫原子以可獨立地經氟原子、氯原子、溴原子或碘原子取代者較佳。又,X以甲基、苯基、氟苯基、甲氧基、苯氧基、甲基硫基、苯基硫基、二乙胺基或二苯胺基較佳。
含氮雜環碳烯配位基以通式(3)或(4)表示。
於通式(3)或(4),R1
及R2
表示烷基、環烷基、多環烷基或芳基,但烷基、環烷基、芳基與定義為上述X之碳原子上可經取代者同意義。
上述多環烷基較好為碳原子數6至10之多環烷基,可列舉例如雙環-[2.1.1]-己基、雙環-[2.2.1]-庚基、雙環-[2.2.2]-辛基、雙環-[3.3.0]-辛基、雙環-[4.3.0]-壬基、雙環-[4.4.0]-辛基、金剛烷基等。
R3
、R4
、R5
及R6
表示氫原子、鹵素原子、烷基、烯基、芳基、芳烷基、烷氧基、芳氧基、硝基、氰基或二烷胺基,但烷基、烯基、芳基、芳烷基、烷氧基、芳氧基或二烷胺基與定義為上述X之碳原子上可經取代者同意義。
R3
、R4
、R5
及R6
鄰接之基之間,可與該等鍵結之碳原子一同形成環。於通式(3),R3
及R4
為與該等鍵結之碳原子一同形成環時之環可列舉例如環戊烯環、環己烯環、環庚烯環、苯環、萘環等碳原子數5至10之碳環。又,於通式(4),R3
(或R4
)及R5
(或R6
)與該等鍵結之碳原子一同形成環時之環可列舉例如環戊烷環、環己烷環、環庚烷環、苯環、萘環等碳原子數5至10之碳環。
又,R1
至R6
表示含碳原子之基時,該碳原子上之1個或複數氫原子可經鹵素原子、烷基、環烷基、烯基、芳基、芳烷基、烷氧基或芳氧基取代,此等亦與定義為上述X之碳原子上可經取代者同意義。此等中,R1
及R2
為選自碳原子數1至6之烷基、碳原子數6至14之芳基或碳原子數6至10之多環烷基之基,上述芳基之碳原子上之1個或複數氫原子較宜為可獨立地經碳原子數1至6之烷基取代者,以三級丁基、2,6-二異丙基苯基、2,4,6-三甲基苯基或金剛烷基較佳,R3
、R4
、R5
及R6
較好為氫原子或鹵素原子,又以氫原子或氯原子較佳。
本發明含氮雜環碳烯配位基(L)之具體例可列舉例如式(5)至(14)表示之化合物。
本發明通式(1)或(2)表示之經取代苯基乙炔基金-含氮雜環碳烯錯合物,經由例如反應步驟式(1)表示之將通式(Ia)或(Ib)之經取代苯基乙炔基金膦錯合物與含氮雜環碳烯配位基(L)進行反應獲得
式中,X及L與上述者同意義,P表示單牙膦配位基。
上述單牙膦配位基(P)可列舉例如雙(五氟苯基)苯基膦、(4-溴苯基)二苯基膦、二烯丙基苯基膦、二環己基苯基膦、二乙基苯基膦、4-(二甲胺基)苯基二苯基膦、二甲基苯基膦、二苯基(2-甲氧基苯基)膦、二苯基(五氟苯基)膦、二苯基丙基膦、二苯基-2-吡啶基膦、二苯基(對-甲苯基)膦、二苯基乙烯基膦、乙基二苯基膦、異丙基二苯基膦、甲基二苯基膦、三(苯甲基)膦、三丁基膦、三-三級丁基膦、三環己基膦、三環戊基膦、三乙基膦、三-2-呋喃基膦、三異丁基膦、三異丙基膦、三丙基膦、三甲基膦、三辛基膦、三苯基膦、三(4-氯苯基)膦、三(3-氯苯基)膦、三(2,6-二甲氧基苯基)膦、三(4-氟苯基)膦、三(3-氟苯基)膦、三(4-甲氧基苯基)膦、三(3-甲氧基苯基)膦、三(2-甲氧基苯基)膦、三(4-三氟甲基苯基)膦、三(五氟苯基)膦、三(2,4,6-三甲氧基苯基)膦、三(2,4,6-三甲基苯基)膦、三-間-甲苯基膦、三-鄰-甲苯基膦、三-對-甲苯基膦、苯甲基二苯基膦、雙(2-甲氧基苯基)苯基膦、二苯基環己基膦、2-(二-三級丁基膦基)聯苯、2-(二環己基膦基)聯苯、新薄荷基(neomenthyl)二苯基膦、對-甲苯基二苯基膦、三烯丙基膦、參(2,4,4-三甲基戊基)膦、三(1-萘基)膦、參(羥基甲基)膦、參(羥基丙基)膦等。此等亦可直接使用市售品。
上述經取代苯基乙炔基金膦錯合物經由例如反應步驟式(2)表示,將金鹵素膦錯合物與經取代之苯基乙炔進行反應獲得(參照例如Journal of Chemical Society,Dalton Trans.,1986,411)
式中,X及P與上述者同意義,Y表示鹵素原子。
又,上述金鹵素膦錯合物可經由習知之方法合成(參照例如實驗化學講座,第4版,丸善公司,455頁,18卷(1991年))。
上述含氮雜環碳烯配位基可直接使用市售品,亦可使用例如經由習知之方法合成者(參照例如J.Am.Chem.Soc.,114
,5530(1992)及國際公開第98/27064號公報)。
通式(15)或(16)表示之上述經取代苯基乙炔化合物
式中,X與上述者同意義可經由例如反應步驟式(3)所示,由對應之經取代苯基溴化物根據習知之方法(例如Journal of Organic Chemistry,1985,50卷,1763)合成。
又,亦可經由將乙炔基取代芳族羧酸衍生後(特開平3-227954號公報),將羧基衍生為種種羧酸衍生物而合成(實驗化學講座第4版22卷有機合成IV丸善(股)公司)。
在本發明經取代苯基乙炔基金-含氮雜環碳烯錯合物之合成中,含氮雜環碳烯配位基之使用量相對於經取代苯基乙炔基金膦錯合物1莫耳,較好為1至3莫耳,更好為1至1.5莫耳。
於本發明經取代苯基乙炔基金-含氮雜環碳烯錯合物之合成中使用之溶劑只要不阻礙反應者則並無特別限制,使用例如四氫呋喃、呋喃、二烷、四氫吡喃、二乙基醚、二異丙基醚、二丁基醚等醚類;戊烷、己烷、庚烷、辛烷等脂肪族烴類;苯、甲苯、二甲苯等芳族烴類;二氯甲烷、二氯乙烷、二氯丙烷等鹵化脂肪族烴類;氯苯等鹵化芳族烴類。又,此等溶劑可單獨使用,亦可混合使用二種以上。
上述溶劑之使用量根據反應液之均一性或攪拌性適當調節,相對於經取代苯基乙炔基金膦錯合物1莫耳較好為1至30L,更好為5至20L。
本發明之經取代苯基乙炔基金-含氮雜環碳烯錯合物之合成根據例如將經取代苯基乙炔基金膦錯合物、含氮雜環碳烯配位基(經由含氮雜環鹵化氫與鹼進行反應生成)及溶劑混合,邊攪拌邊進行反應等方法進行。此時之反應溫度較好為0至120℃,更好為20至100℃,反應壓力並無特別限制。
本發明之經取代苯基乙炔基金-含氮雜環碳烯錯合物在反應完成後經由中和、萃取、過濾、濃縮、蒸餾、再結晶、昇華、層析法等習知之方法分離.生成。
本發明之經取代苯基乙炔基金-含氮雜環碳烯錯合物可列舉例如以下式(17)至(26)表示之化合物。
本發明之經取代苯基乙炔基金-含氮雜環碳烯錯合物根據實施例記載之物性值,暗示適合作為有機電激發光元件使用。
接著,列舉實施例對本發明作具體之說明,但本發明並不只限於此等實施例。
在氬氣下,在20mL施嫰克管(Schlenk tube)中加入氯化1,3-雙(2,6-二異丙基苯基)咪唑(IPrH+
Cl-
;285mg,0.67mmol)、三級丁醇鉀(85質量%物、114mg,0.86mmol)、四氫呋喃(10mL),於室溫攪拌15分鐘後減壓蒸餾除去四氫呋喃。加入甲苯(10mL),於70℃攪拌5分鐘後過濾反應混合物,將濾液滴入加有3-苯甲醯基苯基乙炔基(三苯基膦)金(340mg,0.51mmol)、甲苯10mL之另一支30mL施嫰克管中。滴下後將反應混合物於70℃加熱3小時。將反應混合物冷卻至室溫後在反應混合液中加入甲苯,水洗使pH為7。用硫酸鈉乾燥後用蒸發器減壓蒸餾除去溶劑。反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=5/1至3/1)精製,獲得之固體用己烷洗淨過濾,獲得白色固體之目標物0.29g(收率72%)。
1
H-NMR(300MHz,CDCl3
)δ:7.74-7.12(m,17H),2.64-2.55(sept,4H),1.37(d,12H),1.21(d,12H)
EI-MS(M/Z):790(M)+
發光分析(CHCl3
,77K,Ex240nm)λ(nm):446(max)熱分析:融點:224℃元素分析 觀測值C:63.74,H:5.58,N:3.68理論值C:63.79,H:5.74,N:3.54
在氬氣下,在20mL施嫰克管中加入氯化1,3-雙(2,6-二異丙基苯基)咪唑(IPrH+
Cl-
;259mg,0.61mmol)、三級丁醇鉀(85質量%物、104mg,0.79mmol)、四氫呋喃(10mL),於室溫攪拌15分鐘後減壓蒸餾除去四氫呋喃。加入甲苯(10mL),於70℃攪拌5分鐘後過濾反應混合物,將濾液滴入加有[3-(4’-氟苯甲醯基)苯基乙炔基](三苯基膦)金(320mg,0.47mmol)、甲苯10mL之另一支30mL施嫰克管中。滴下後將反應混合物於70℃加熱3小時。將反應混合物冷卻至室溫後在反應混合液中加入甲苯,水洗使pH為7。用硫酸鈉乾燥後用蒸發器減壓蒸餾除去溶劑。反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=5/1)精製,獲得之固體用己烷洗淨過濾,獲得白色固體之目標物0.32g(收率84%)。
1
H-NMR(300MHz,CDCl3
)δ:7.76-7.07(m,16H),2.62-2.56(sept,4H),1.37(d,12H),1.21(d,12H)
EI-MS(M/Z):808(M)+
發光分析(CHCl3
,77K,Ex240nm)λ(nm):442(max)熱分析:融點:224℃元素分析 觀測值C:62.35,H:5.44,N:3.44理論值C:62.37,H:5.48,N:3.46
在氬氣下,在20mL施嫰克管中加入氯化1,3-雙(2,6-二異丙基苯基)咪唑(IPrH+
Cl-
;272mg,0.64mmol)、三級丁醇鉀(85質量%物、111mg,0.84mmol)、四氫呋喃(10mL),於室溫攪拌15分鐘後減壓蒸餾除去四氫呋喃。加入甲苯(10mL),於70℃攪拌5分鐘後過濾反應混合物,將濾液滴入加有3-乙醯基苯基乙炔基(三苯基膦)金(298mg,0.49mmol)、甲苯10mL之另一支30mL施嫰克管中。滴下後將反應混合物於70℃加熱3小時。將反應混合物冷卻至室溫後在反應混合液中加入甲苯,水洗使pH為7。用硫酸鈉乾燥後用蒸發器減壓蒸餾除去溶劑。反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=5/1至3/1)精製,獲得之固體用己烷洗淨過濾,獲得白色固體之目標物0.34g(收率95%)。
1
H-NMR(300MHz,CDCl3
)δ:7.88-7.13(m,12H),2.65-2.49(sept,4H),2.49(s,3H),1.44(d,12H),1.21(d,12H)
EI-MS(M/Z):728(M)+
發光分析(CHCl3,77K,Ex240nm)λ(nm):440(max)熱分析:融點:224℃元素分析 觀測值C:60.73,H:5.95,N:3.97理論值C:60.98,H:5.95,N:3.84
在氬氣下,在20mL施嫰克管中加入氯化1,3-雙(2,6-二異丙基苯基)咪唑(IPrH+
Cl-
;298mg,0.70mmol)、三級丁醇鉀(85質量%物、120mg,0.91mmol)、四氫呋喃(11mL),於室溫攪拌15分鐘後減壓蒸餾除去四氫呋喃。加入甲苯(11mL),於70℃攪拌5分鐘後過濾反應混合物,將濾液滴入加有3-(二乙胺基羰基)苯基乙炔基(三苯基膦)金(356mg,0.54mmol)、甲苯11mL之另一支30mL施嫰克管中。滴下後將反應混合物於70℃加熱3小時。將反應混合物冷卻至室溫後在反應混合液中加入甲苯,水洗使pH為7。用硫酸鈉乾燥後用蒸發器減壓蒸餾除去溶劑。反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=5/1至1/1)精製,獲得之固體用己烷洗淨過濾,獲得白色固體之目標物0.38g(收率91%)。
1
H-NMR(300MHz,CDCl3
)δ:7.52-7.03(m,12H),3.31(m,4H),2.65-2.54(sept,4H),1.44(d,12H),1.21(d,12H),1.09(m,6H)
EI-MS(M/Z):785(M)+
發光分析(CHCl3
,77K,Ex240nm)λ(nm):421(max)熱分析:融點:218℃元素分析 觀測值C:61.02,H:6.30,N:5.32理論值C:61.14,H:6.41,N:5.35
在氬氣下,在20mL施嫰克管中加入氯化1,3-雙(2,6-二異丙基苯基)咪唑(IPrH+
Cl-
;319mg,0.75mmol)、三級丁醇鉀(85質量%物、129mg,0.98mmol)、四氫呋喃(12mL),於室溫攪拌15分鐘後減壓蒸餾除去四氫呋喃。加入甲苯(12mL),於70℃攪拌5分鐘後過濾反應混合物,將濾液滴入加有3-(二苯胺基羰基)苯基乙炔基(三苯基膦)金(356mg,0.54mmol)、甲苯12mL之另一支30mL施嫰克管中。滴下後將反應混合物於70℃加熱3小時。將反應混合物冷卻至室溫後在反應混合液中加入甲苯,水洗使pH為7。用硫酸鈉乾燥後用蒸發器減壓蒸餾除去溶劑。反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=5/1)精製,獲得之固體用己烷洗淨過濾,獲得白色固體之目標物0.48g(收率95%)。
1
H-NMR(300MHz,CDCl3
)δ:7.54-6.83(m,22H),2.62-2.55(sept,4H),1.37(d,12H),1.21(d,12H)
EI-MS(M/Z):881(M)+
發光分析(CHCl3
,77K,Ex240nm)λ(nm):427(max)熱分析:融點:260℃元素分析 觀測值C:65.23,H:5.62,N:4.87理論值C:65.37,H:5.71,N:4.76
在氬氣下,在20mL施嫰克管中加入氯化1,3-雙(2,6-二異丙基苯基)咪唑(IPrH+
Cl-
;282mg,0.66mmol)、三級丁醇鉀(85質量%物、114mg,0.86mmol)、四氫呋喃(10mL),於室溫攪拌15分鐘後減壓蒸餾除去四氫呋喃。加入甲苯(10mL),於70℃攪拌5分鐘後過濾反應混合物,將濾液滴入加有3-(甲氧基羰基)苯基乙炔基(三苯基膦)金(315mg,0.51mmol)、甲苯10mL之另一支30mL施嫰克管中。滴下後將反應混合物於70℃加熱3小時。將反應混合物冷卻至室溫後在反應混合液中加入甲苯,水洗使pH為7。用硫酸鈉乾燥後用蒸發器減壓蒸餾除去溶劑。反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=5/1)精製,獲得之固體用己烷洗淨過濾,獲得白色固體之目標物0.31g(收率80%)。
1
H-NMR(300MHz,CDCl3
)δ:7.98-7.12(m,12H),3.83(s,3H),2.67-2.54(sept,4H),1.38(d,12H),1.23(d,12H)EI-MS(M/Z):744(M)+
發光分析(CHCl3
,77K,Ex240nm)λ(nm):426(max)熱分析:融點:205℃元素分析 觀測值C:59.75,H:5.69,N:3.77理論值C:59.67,H:5.82,N:3.76
在氬氣下,在20mL施嫰克管中加入氯化1,3-雙(2,6-二異丙基苯基)咪唑(IPrH+
Cl-
;212mg,0.50mmol)、三級丁醇鉀(85質量%物、86mg,0.65mmol)、四氫呋喃(8mL),於室溫攪拌15分鐘後減壓蒸餾除去四氫呋喃。加入甲苯(8mL),於70℃攪拌5分鐘後過濾反應混合物,將濾液滴入加有3-(苯氧基羰基)苯基乙炔基(三苯基膦)金(260mg,0.38mmol)、甲苯8mL之另一支30mL施嫰克管中。滴下後將反應混合物於70℃加熱3小時。將反應混合物冷卻至室溫後在反應混合液中加入甲苯,水洗使pH為7。用硫酸鈉乾燥後用蒸發器減壓蒸餾除去溶劑。反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=5/1)精製,獲得之固體用己烷洗淨過濾,獲得白色固體之目標物0.22g(收率70%)。
1
H-NMR(300MHz,CDCl3
)δ:8.16-7.13(m,17H),2.63-2.56(sept,4H),1.38(d,12H),1.22(d,12H)
EI-MS(M/Z):806(M)+
發光分析(CHCl3
,77K,Ex240nm)λ(nm):427(max)熱分析:融點:224℃元素分析 觀測值C:62.17,H:5.52,N:3.48理論值C:62.53,H:5.62,N:3.47
在氬氣下,在20mL施嫰克管中加入氯化1,3-雙(2,6-二異丙基苯基)咪唑(IPrH+
Cl-
;221mg,0.52mmol)、三級丁醇鉀(85質量%物、90mg,0.68mmol)、四氫呋喃(8mL),於室溫攪拌15分鐘後減壓蒸餾除去四氫呋喃。加入甲苯(8mL),於70℃攪拌5分鐘後過濾反應混合物,將濾液滴入加有3-(甲基硫基羰基)苯基乙炔基(三苯基膦)金(256mg,0.4mmol)、甲苯8mL之另一支30mL施嫰克管中。滴下後將反應混合物於70℃加熱3小時。將反應混合物冷卻至室溫後在反應混合液中加入甲苯,水洗使pH為7。用硫酸鈉乾燥後用蒸發器減壓蒸餾除去溶劑。反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=5/1)精製,獲得之固體用己烷洗淨過濾,獲得白色固體之目標物0.22g(收率73%)。
1
H-NMR(300MHz,CDCl3
)δ:7.91-7.13(m,12H),2.67-2.54(sept,4H),2.40(s,3H),1.38(d,12H),1.22(d,12H)
EI-MS(M/Z):760(M)+
發光分析(CHCl3
,77K,Ex240nm)λ(nm):434(max)熱分析:融點:212℃元素分析 觀測值C:58.15,H:5.70,N:3.80理論值C:58.41,H:5.70,N:3.68
在氬氣下,在20mL施嫰克管中加入氯化1,3-雙(2,6-二異丙基苯基)咪唑(IPrH+
Cl-
;212mg,0.50mmol)、三級丁醇鉀(85質量%物、206mg,0.49mmol)、四氫呋喃(8mL),於室溫攪拌15分鐘後減壓蒸餾除去四氫呋喃。加入甲苯(8mL),於70℃攪拌5分鐘後過濾反應混合物,將濾液滴入加有3-(苯基硫基羰基)苯基乙炔基(三苯基膦)金(260mg,0.37mmol)、甲苯8mL之另一支30mL施嫰克管中。滴下後將反應混合物於70℃加熱3小時。將反應混合物冷卻至室溫後在反應混合液中加入甲苯,水洗使pH為7。用硫酸鈉乾燥後用蒸發器減壓蒸餾除去溶劑。反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=5/1)精製,獲得之固體用己烷洗淨過濾,獲得白色固體之目標物0.17g(收率56%)。
1
H-NMR(300MHz,CDCl3
)δ:7.99-7.13(m,17H),2.63-2.56(sept,4H),1.39(d,12H),1.22(d,12H)
EI-MS(M/Z):822(M)+
發光分析(CHCl3
,77K,Ex240nm)λ(nm):435(max)熱分析:融點:223℃元素分析 觀測值C:60.94,H:5.49,N:3.50理論值C:61.30,H:5.51,N:3.40
在氬氣下,在20mL施嫰克管中加入氯化1,3-雙(2,6-二異丙基苯基)咪唑(IPrH+
Cl-
;278mg,0.66mmol)、三級丁醇鉀(85質量%物、112mg,0.85mmol)、四氫呋喃(10mL),於室溫攪拌15分鐘後減壓蒸餾除去四氫呋喃。加入甲苯(10mL),於70℃攪拌5分鐘後過濾反應混合物,將濾液滴入加有2-苯甲醯基苯基乙炔基(三苯基膦)金(335mg,0.50mmol)、甲苯10mL之另一支30mL施嫰克管中。滴下後將反應混合物於70℃加熱3小時。將反應混合物冷卻至室溫後在反應混合液中加入甲苯,水洗使pH為7。用硫酸鈉乾燥後用蒸發器減壓蒸餾除去溶劑。反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=5/1)精製,獲得之固體用己烷洗淨過濾,獲得白色固體之目標物0.37g(收率93%)。
1
H-NMR(300MHz,CDCl3
)δ:7.67-7.06(m,17H),2.53-2.44(sept,4H),1.23(d,12H),1.18(d,12H)
EI-MS(M/Z):790(M)+
發光分析(CHCl3
,77K,Ex240nm)λ(nm):457(max)熱分析:融點:242℃元素分析 觀測值C:63.77,H:5.51,N:3.54理論值C:63.79,H:5.74,N:3.54
碳烯錯合物經由磷光螢光光度計測定發光光譜(在氯仿中,溫度77K(凱氏(Kelvin))、紫外線照射下)後,結果顯示發光最大波長421nm至457nm、CIE色度座標(0.149,0.085)至(0.153,0.208)之藍色磷光發光。
又,熱分析之結果,本發明之經取代苯基乙炔基金-含氮雜環碳烯錯合物之融點都在200℃以上,暗示可適當作為有機激電發光元件使用。
(第1步驟)將15mL施嫰克管進行氬氣取代,加入3-溴二苯甲酮1.57mg(6mmol)、四(三苯基膦)鈀70mg(0.06mmol)、哌啶6mL、2-甲基-3-丁炔-2-醇640 μ L(6.6mmol),於100℃攪拌1.25小時。
反應混合物中加入飽和氯化銨水溶液後用二乙基醚萃取,用硫酸鎂乾燥,用蒸發器減壓蒸餾除去溶劑。獲得之反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=5/1)精製,獲得黃色液體之目標物3-(3-羥基-3-甲基-1-丁炔基)二苯甲酮1.46g(收率92%)。
1
H-NMR(300MHz,CDCl3
)δ:7.83-7.40(m,9H),2.09(s,1H),1.61(s,6H)
EI-MS(M/Z):264(M)+
(第2步驟)在備有回流管之100mL2口燒瓶中加入3-(3-羥基-3-甲基-1-丁炔基)二苯甲酮1.45g(5.5mmol)、氫氧化鈉(Kishida化學公司,0.7mm粒狀,98%)230mg(5.8mmol),將內部進行氬氣取代。加入甲苯30mL,於120℃回流0.5小時。反應混合液中加入甲苯,用飽和氯化銨水溶液洗淨,用硫酸鎂乾燥,用蒸發器減壓蒸餾除去溶劑。反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=30/1)精製,獲得橘色固體之3-乙炔基二苯甲酮0.9g(收率80%)。
1
H-NMR(300MHz,CDCl3
)δ:7.91-7.26(m,9H),3.12(s,1H)
EI-MS(M/Z):206(M)+
(第1步驟)將15mL施嫰克管進行氬氣取代,加入3-溴-4’-氟二苯甲酮1.4g(5mmol)、肆(三苯基膦)鈀58mg(0.05mmol)、1-甲基哌啶5mL、2-甲基-3-丁炔-2-醇533 μ L(5.5mmol),於100℃攪拌4.5小時。
反應混合物中加入飽和氯化銨水溶液後用二乙基醚萃取,用硫酸鎂乾燥,用蒸發器減壓蒸餾除去溶劑。獲得之反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=5/1)精製,獲得橘色結晶之目標物4-氟-3’-(3-羥基-3-甲基-1-丁炔基)二苯甲酮1.11g。收量(收率79%)。
1
H-NMR(300MHz,CDCl3
)δ:7.83-7.15(m,8H),2.15(s,1H),1.62(s,6H)
EI-MS(M/Z):282(M)+
(第2步驟)在備有回流管之100mL2口燒瓶中加入4-氟-3’-(3-羥基-3-甲基-1-丁炔基)二苯甲酮1.11mg(3.9mmol)、氫氧化鈉(Kishida化學公司,0.7mm粒狀,98%)165mg(4.1mmol),將內部進行氬氣取代。加入甲苯20mL,於120℃回流0.5小時。反應混合液中加入甲苯,用飽和氯化銨水溶液洗淨,用硫酸鎂乾燥,用蒸發器減壓蒸餾除去溶劑。反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=10/1)精製,獲得黃色固體之3-乙炔基-4’-氟二苯甲酮0.5g(收率53%)。
1
H-NMR(300MHz,CDCl3
)δ:7.87-7.14(m,8H),3.13(s,1H)
EI-MS(M/Z):224(M)+
(第1步驟)將30mL施嫰克管進行氬氣取代,加入3-溴苯乙酮1.99mL(15mmol)、肆(三苯基膦)鈀173mg(0.15mmol)、哌啶15mL、2-甲基-3-丁炔-2-醇1.6mL(16.5mmol),於100℃攪拌1.25小時。
反應混合物中加入飽和氯化銨水溶液後用二乙基醚萃取,用硫酸鎂乾燥,用蒸發器減壓蒸餾除去溶劑。獲得之反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=5/1)精製,獲得橘色液體之目標物3-(3-羥基-3-甲基-1-丁炔基)苯乙酮2.98g(收率98%)。
1
H-NMR(300MHz,CDCl3
)δ:8.00-7.38(m,4H),2.59(s,3H),2.3(s,1H),1.63(s,6H)
EI-MS(M/Z):202(M)+
(第2步驟)在備有回流管之200mL2口燒瓶中加入3-(3-羥基-3-甲基-1-丁炔基)苯乙酮2.98g(14.7mmol)、氫氧化鈉(Kishida化學公司,0.7mm粒狀,98%)0.62g(15.4mmol),將內部進行氬氣取代。加入甲苯75mL,於120℃回流0.5小時。反應混合液中加入甲苯,用飽和氯化銨水溶液洗淨,用硫酸鎂乾燥,用蒸發器減壓蒸餾除去溶劑。將反應粗生成物於70℃溶解於己烷40mL,過濾不溶物後將濾液冷卻,獲得白色固體之目標物3-乙炔基苯乙酮(1.43g,收率67%)。
1
H-NMR(300MHz,CDCl3
)δ:8.07-7.39(m,4H),3.14(s,1H),2.61(s,3H)
EI-MS(M/Z):144(M)+
將20mL施嫰克管進行氬氣取代,加入間-乙炔基苯甲酸1.02g(7mmol)、亞硫醯氯(thionyl chloride)5g(42mmol),於50℃攪拌2小時後減壓蒸餾除去過剩之亞硫醯氯,獲得間-乙炔基苯甲醯氯(benzoyl chloride)。在獲得之間-乙炔基苯甲醯氯中,於冰冷下加入將二乙胺1.49mL(14.4mmol)溶解於二氯甲烷7mL形成之溶液後將溫度設定為室溫,攪拌1小時。攪拌完成後減壓蒸餾除去二氯甲烷,殘渣中加入水35mL,用二乙基醚35mL萃取,用硫酸鎂乾燥,用蒸發器減壓蒸餾除去溶劑。獲得之反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=5/1:3/1)精製,獲得淡黃色液體之目標物3-乙炔基-N,N-二乙基苯甲醯胺1.3g(收率92%)。
1
H-NMR(300MHz,cDCl3
)δ:7.76-7.22(m,4H),3.54(m,2H),3.25(m,2H),3.11(s,1H),1.26(m,3H)1.11(m,3H)
EI-MS(M/Z):201(M)+
將20mL施嫰克管進行氬氣取代,加入間-乙炔基苯甲酸1.02g(7mmol)、亞硫醯氯5g(42mmol),於50℃攪拌2小時後減壓蒸餾除去過剩之亞硫醯氯,獲得間-乙炔基苯甲醯氯。在獲得之間-乙炔基苯甲醯氯中,於冰冷下加入將二苯胺2.44g(14.4mmol)溶解於二氯甲烷7mL形成之溶液後將溫度設定為室溫,攪拌1小時。攪拌完成後減壓蒸餾除去二氯甲烷,殘渣中加入水35mL,用乙酸乙酯35mL萃取,用硫酸鎂乾燥,用蒸發器減壓蒸餾除去溶劑。獲得之反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=10/1)精製,獲得淡黃色液體之目標物3-乙炔基-N,N-二苯基苯甲醯胺0.7g(收率35%)。
1
H-N MR(300MHz,CDCl3
)δ:7.63-6.91(m,14H),3.03(s,1H)
EI-MS(M/Z):297(M)+
將20mL施嫰克管進行氬氣取代,加入間-乙炔基苯甲酸1.02g(7mmol)、亞硫醯氯5g(42mmol),於50℃攪拌2小時後減壓蒸餾除去過剩之亞硫醯氯,獲得間-乙炔基苯甲醯氯。在獲得之間-乙炔基苯甲醯氯中,於冰冷下加入將甲醇298 μ L(7.35mmol)、吡啶3.4mL(42mmol)溶解於二氯甲烷7mL形成之溶液後將溫度設定為室溫,攪拌1小時。攪拌完成後減壓蒸餾除去二氯甲烷,殘渣中加入水35mL,用二乙基醚35mL萃取,用硫酸鎂乾燥,用蒸發器減壓蒸餾除去溶劑。獲得之反應粗生成物於70℃溶解於己烷15mL,過濾不溶物後將濾液冷卻,獲得黃色固體之目標物3-乙炔基苯甲酸乙酯0.74g(收率66%)。
1
H-NMR(300MHz,CDCl3
)δ:8.17-7.38(m,4H),3.95(s,3H),3.11(s,1H)
EI-MS(M/Z):160(M)+
將20mL施嫰克管進行氬氣取代,加入間-乙炔基苯甲酸1.02g(7mmol)、亞硫醯氯5g(42mmol),於50℃攪拌2小時後減壓蒸餾除去過剩之亞硫醯氯,獲得間-乙炔基苯甲醯氯。在獲得之間-乙炔基苯甲醯氯中,於冰冷下加入將苯酚692mg(7.35mmol)、吡啶3.4mL(42mmol)溶解於二氯甲烷7mL形成之溶液後將溫度設定為室溫,攪拌1小時。攪拌完成後減壓蒸餾除去二氯甲烷,殘渣中加入水35mL,用乙酸乙酯35mL萃取,用硫酸鎂乾燥,用蒸發器減壓蒸餾除去溶劑。獲得之反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=10/1)精製,獲得黃色固體之目標物3-乙炔基苯甲酸苯酯0.55g(收率35%)。
1
H-NMR(300MHz,CDCl3
)δ:8.34-6.69(m,9H),3.15(s,1H)
EI-MS(M/Z):222(M)+
將20mL施嫰克管進行氬氣取代,加入間-乙炔基苯甲酸1.02g(7mmol)、亞硫醯氯5g(42mmol),於50℃攪拌2小時後減壓蒸餾除去過剩之亞硫醯氯,獲得間-乙炔基苯甲醯氯。在獲得之間-乙炔基苯甲醯氯中加入二氯甲烷7mL,冰冷後加入甲硫醇(methanethiolate)鈉515mg(7.35mmol),將溫度設定為室溫,攪拌3小時。攪拌完成後減壓蒸餾除去二氯甲烷,殘渣中加入水35mL,用乙酸乙酯35mL萃取,用硫酸鎂乾燥,用蒸發器減壓蒸餾除去溶劑。獲得之反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=10/1)精製,獲得黃色固體之目標物3-乙炔基-硫代苯甲酸-S-甲酯0.49g(收率40%)。
1
H-NMR(300MHz,CDCl3
)δ:8.09-7.39(m,4H),3.14(s,1H),2.48(s,3H)
EI-MS(M/Z):176(M)+
將20mL施嫰克管進行氬氣取代,加入間-乙炔基苯甲酸1.02g(7mmol)、亞硫醯氯5g(42mmol),於50℃攪拌2小時後減壓蒸餾除去過剩之亞硫醯氯,獲得間-乙炔基苯甲醯氯。在獲得之間-乙炔基苯甲醯氯中加入THF7mL,冰冷後加入苯硫醇鈉971mg(7.35mmol)後將溫度設定為室溫,攪拌2小時。攪拌完成後減壓蒸餾除去THF,殘渣中加入水35mL,用乙酸乙酯35mL萃取,用硫酸鎂乾燥,用蒸發器減壓蒸餾除去溶劑。獲得之反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=20/1)精製,獲得黃色固體之目標物3-乙炔基-硫代苯甲酸-S-苯酯0.51g(收率31%)。
1
H-NMR(300MHz,CDCl3
)δ:8.15-7.39(m,9H),3.16(s,1H)
EI-MS(M/Z):238(M)+
在氬氣下,在30mL施嫰克管中加入Au(PPh3
)Cl(297mg,0.60mmol)、3-乙炔基二苯甲酮(186mg,0.9mmol)、乙醇(12mL)後滴下乙醇鈉(247 μ L,0.63mmol:濃度2.55mol/L(公升)之乙醇溶液),於室溫攪拌17小時。過濾反應後獲得之白色沉澱,用乙醇(12mL×3次)、水(12mL×3次)及乙醇(6mL×3次)依序洗淨,經由真空乾燥獲得白色粉末之目標化合物0.38g(收率96%)。
1
H-NMR(300MHz,CDCl3
)δ:7.88-7.26(m,24H)
FAB-MS(M/Z):665(M+H)+
發光分析(CHCl3
,77K,Ex240nm)λ(nm):441(max)元素分析 觀測值C:59.57,H:3.57理論值C:59.65,H:3.64
在氬氣下,在30mL施嫰克管中加入Au(PPh3
)Cl(297mg,0.60mmol)、3-乙炔基-4’-氟二苯甲酮(202mg,0.9mmol)、乙醇(12mL)後滴下乙醇鈉(247 μ L,0.63mmol:濃度2.55mol/L(公升)之乙醇溶液),於室溫攪拌17小時。過濾反應後獲得之白色沉澱,用乙醇(12mL×3次)、水(12mL×3次)及乙醇(6mL×3次)依序洗淨,經由真空乾燥獲得白色粉末之目標化合物0.36g(收率89%)。
1
H-NMR(300MHz,cDcl3
)δ:7.86-7.11(m,23H)
FAB-MS(M/Z):683(M+H)+
發光分析(CHCl3
,77K,Ex240nm)λ(nm):424(max)元素分析 觀測值C:58.26,H:3.32理論值C:58.08,H:3.40
在氬氣下,在30mL施嫰克管中加入Au(PPh3
)Cl(297mg,0.60mmol)、3-乙炔基苯乙酮(130mg,0.9mmol)、乙醇(12mL)後滴下乙醇鈉(247 μ L,0.63mmol:濃度2.55mol/L(公升)之乙醇溶液),於室溫攪拌17小時。過濾反應後獲得之白色沉澱,用乙醇(12mL×3次)、水(12mL×3次)及乙醇(6mL×3次)依序洗淨,經由真空乾燥獲得白色粉末之目標化合物0.34g(收率94%)。
1
H-NMR(300MHz,CDCl3
)δ:8.09-7.26(m,19H),2.57(s,3H)
FAB-MS(M/Z):603(M+H)+
發光分析(CHCl3
,77K,Ex240nm)λ(nm):434(max)元素分析 觀測值C:55.74,H:3.73理論值C:55.83,H:3.68
在氬氣下,在30mL施嫰克管中加入Au(PPh3
)Cl(297mg,0.60mmol)、3-乙炔基-N,N-二乙基苯甲醯胺(181mg,0.9mmol)、乙醇(12mL)後滴下乙醇鈉(247 μ L,0.63mmol:濃度2.55mol/L(公升)之乙醇溶液),於室溫攪拌17小時。減壓蒸餾除去乙醇,殘渣中加入二氯甲烷,水洗後用硫酸鈉乾燥,用蒸發器減壓蒸餾除去溶劑,獲得油狀物之目標化合物0.36g(收率90%)。
1
H-NMR(300MHz,cDCl3
)δ:7.59-7.20(m,19H),3.40(d,4H),1.15(d,6H)
FAB-MS(M/Z):660(M+H)+
在氬氣下,在30mL施嫰克管中加入Au(PPh3
)Cl(297mg,0.60mmol)、3-乙炔基-N,N-二苯基苯甲醯胺(268mg,0.9mmol)、乙醇(12mL)後滴下乙醇鈉(247 μ L,0.63mmol:濃度2.55mol/L(公升)之乙醇溶液),於室溫攪拌17小時。過濾反應後獲得之白色沉澱,用乙醇(12mL×3次)、水(12mL×3次)及乙醇(6mL×3次)依序洗淨,經由真空乾燥獲得白色粉末之目標化合物0.41g(收率91%)。
1
H-NMR(300MHz,CDCl3
)δ:7.67-7.06(m,29H)
FAB-MS(M/Z):756(M+H)+
在氬氣下,在30mL施嫰克管中加入Au(PPh3
)Cl(297mg,0.60mmol)、3-乙炔基苯甲酸乙酯(181mg,0.9mmol)、乙醇(12mL)後滴下甲醇鈉(91 μ L,0.63mmol:濃度6.95mol/L(公升)之甲醇溶液),於室溫攪拌17小時。過濾反應後獲得之白色沉澱,用甲醇(12mL×3次)、水(12mL×3次)及甲醇(6mL×3次)依序洗淨,經由真空乾燥獲得白色粉末之目標化合物0.33g(收率88%)。
1
H-NMR(300MHz,CDCl3
)δ:8.20-7.26(m,19H),3.89(s,3H)
FAB-MS(M/Z):619(M+H)+
在氬氣下,在30mL施嫰克管中將Au(PPh3
)Cl(297mg,0.60mmol)、3-乙炔基苯甲酸苯酯(200mg,0.9mmol)、三級丁醇鈉(61mg,0.63mmol)混合,加入戊醇(12mL)後於室溫攪拌17小時。過濾反應後獲得之白色沉澱,用三級丁醇(12mL×3次)、溫水(12mL×3次)及乙醇(6mL×3次)依序洗淨,經由真空乾燥獲得白色粉末之目標化合物0.27g(收率67%)。
1
H-NMR(300MHz,CDCl3
)δ:8.38-7.19(m,24H)
FAB-MS(M/Z):679(M+H)+
在氬氣下,在30mL施嫰克管中將Au(PPh3
)Cl(297mg,0.60mmol)、3-乙炔基-硫代苯甲酸-S-甲酯(159mg,0.9mmol)、三級丁醇鈉(61mg,0.63mmol)混合,加入戊醇(12mL)後於室溫攪拌17小時。過濾反應後獲得之白色沉澱,用三級丁醇(12mL×3次)、溫水(12mL×3次)及乙醇(6mL×3次)依序洗淨,經由真空乾燥獲得白色粉末之目標化合物0.27g(收率70%)。
1
H-NMR(300MHz,CDCl3
)δ:8.14-7.31(m,19H),2.46(s,3H)
FAB-MS(M/Z):635(M+H)+
在氬氣下,在30mL施嫰克管中將Au(PPh3
)Cl(297mg,0.60mmol)、3-乙炔基-硫代苯甲酸-S-苯酯(215mg,0.9mmol)、三級丁醇鈉(61mg,0.63mmol)混合,加入戊醇(12mL)後於室溫攪拌17小時。過濾反應後獲得之白色沉澱,用三級丁醇(12mL×3次)、溫水(12mL×3次)及乙醇(6mL×3次)依序洗淨,經由真空乾燥獲得白色粉末之目標化合物0.27g(收率65%)。
1
H-NMR(300MHz,CDCl3
)δ:8.21-6.99(m,24H)
FAB-MS(M/Z):697(M+H)+
(第1步驟)將15mL施嫰克管進行氬氣取代,加入2-溴二苯甲酮2.61g(10mmol)、肆(三苯基膦)鈀231mg(0.2mmol)、哌啶10mL、2-甲基3-丁炔-2-醇1.9mL(20mmol),於100℃攪拌1小時。
反應混合物中加入飽和氯化銨水溶液後用二乙基醚萃取,用硫酸鎂乾燥,用蒸發器減壓蒸餾除去溶劑。獲得之反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=5/1)精製,獲得黃色液體之目標物2-(3-羥基-3-甲基-1-丁炔基)二苯甲酮2.6g(收率99%)。
1
H-NMR(300MHz,CDCl3
)δ:7.84-7.40(m,9H),1.67(s,1H),1.21(s,6H)
EI-MS(M/Z):264(M)+
(第2步驟)在備有回流管之100mL2口燒瓶中加入二甲基羥基甲基-2-苯甲醯基苯基乙炔2.6g(9.9mmol)、氫氧化鈉(Kishida化學公司,0.7mm粒狀,98%)416mg(10.4mmol),將內部進行氬氣取代。加入甲苯50mL,於120℃回流0.25小時。反應混合液中加入甲苯,用飽和氯化銨水溶液洗淨,用硫酸鎂乾燥,用蒸發器減壓蒸餾除去溶劑。反應粗生成物經由附有矽膠之管柱層析法(己烷/乙酸乙酯=20/1)精製,獲得橘色固體之2-乙炔基二苯甲酮1.7g(收率82%)。
1
H-NMR(300MHz,CDCl3
)δ:7.84-7.42(m,9H),3.04(s,1H)
EI-MS(M/Z):206(M)+
在氬氣下,在30mL施嫰克管中加入Au(PPh3
)Cl(297mg,0.60mmol)、2-乙炔基二苯甲酮(186mg,0.9mmol)、乙醇(12mL)後滴下乙醇鈉(247 μ L,0.63mmol:濃度2.55mol/L(公升)之乙醇溶液),於室溫攪拌17小時。過濾反應後獲得之白色沉澱,用乙醇(12mL×3次)、水(12mL×3次)及乙醇(6mL×3次)依序洗淨,經由真空乾燥獲得白色粉末之目標化合物0.39g(收率97%)。
1
H-NMR(300MHz,CDCl3
)δ:7.88-7.25(m,24H)
FAB-MS(M/Z):665(M+H)+
發光分析(CHCl3
,77K,Ex240nm)λ(nm):459(max)元素分析 觀測值C:59.24,H:3.62理論值C:59.65,H:3.64
本發明之經取代苯基乙炔基金-含氮雜環碳烯錯合物可作為電場發光元件(有機電激發光元件)用發光材料等使用。亦即,具有實現全彩顯示器不可缺之460nm以下藍色區帶之發光,具有可忍受施加電壓時產生之焦耳熱200℃以上之高融點之作為有機電激發光元件用發光材料等使用。
Claims (8)
- 一種通式(1)或(2)表示之經XCO取代苯基乙炔基金-含氮雜環碳烯錯合物:
- 如申請專利範圍第1項之經XCO取代苯基乙炔基金-含氮雜環碳烯錯合物,其中,該多環烷基為選自包括雙環-[2.1.1]-己基、雙環-[2.2.1]-庚基、雙環-[2.2.2]-辛基、雙環-[3.3.0]-辛基、雙環-[4.3.0]-壬基、雙環-[4.4.0]-辛基及金剛烷基之組群者。
- 如申請專利範圍第1項之經XCO取代苯基乙炔基金-含氮雜環碳烯錯合物,其中,該R1 及R2 為三級丁基、2,6-二異丙基苯基、2,4,6-三甲基苯基或金剛烷基,R3 、R4 、R5 及R6 為氫原子或氯原子。
- 如申請專利範圍第3項之經XCO取代苯基乙炔基金-含氮雜環碳烯錯合物,其中,該R1 及R2 為三級丁基、2,6-二異丙基苯基、2,4,6-三甲基苯基或金剛烷基,R3 、R4 、R5 及R6 為氫原子。
- 如申請專利範圍第1項至第4項中任一項之經XCO取代苯基乙炔基金-含氮雜環碳烯錯合物,其中,該X為選自包括苯基、氟苯基、甲基、二乙胺基、二苯胺基、甲氧基、苯氧基、甲基硫基及苯基硫基之組群者。
- 一種如申請專利範圍第1項之經XCO取代苯基乙炔基金-含氮雜環碳烯錯合物之製法,係包含令通式(Ia)或(Ib)表示之經XCO取代苯基乙炔基金膦錯合物與含氮雜環碳烯配位基進行反應之步驟:
- 如申請專利範圍第6項之製法,其中,該反應係對通式(Ia)或(Ib)表示之經XCO取代苯基乙炔基金膦錯合物1莫耳,使用1至3莫耳含氮雜環碳烯配位基者。
- 如申請專利範圍第6項或第7項之製法,其中,該反應係將通式(Ia)或(Ib)表示之經XCO取代苯基乙炔基金膦錯合物與含氮雜環碳烯配位基混合,在溶劑存在下於0至120℃之溫度攪拌而進行者。
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