JP7067302B2 - 重合性化合物及び光学異方体 - Google Patents
重合性化合物及び光学異方体 Download PDFInfo
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- JP7067302B2 JP7067302B2 JP2018116098A JP2018116098A JP7067302B2 JP 7067302 B2 JP7067302 B2 JP 7067302B2 JP 2018116098 A JP2018116098 A JP 2018116098A JP 2018116098 A JP2018116098 A JP 2018116098A JP 7067302 B2 JP7067302 B2 JP 7067302B2
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- 125000000217 alkyl group Chemical group 0.000 claims description 94
- 229910052731 fluorine Inorganic materials 0.000 claims description 48
- 125000001153 fluoro group Chemical group F* 0.000 claims description 48
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- 239000004973 liquid crystal related substance Substances 0.000 claims description 43
- 125000002947 alkylene group Chemical group 0.000 claims description 31
- 229910052801 chlorine Inorganic materials 0.000 claims description 29
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 29
- 239000000463 material Substances 0.000 claims description 23
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- 125000003545 alkoxy group Chemical group 0.000 claims description 13
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
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- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 13
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 12
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- 238000006116 polymerization reaction Methods 0.000 description 9
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 7
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
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- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
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- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 5
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- CLFRCXCBWIQVRN-UHFFFAOYSA-N 2,5-dihydroxybenzaldehyde Chemical compound OC1=CC=C(O)C(C=O)=C1 CLFRCXCBWIQVRN-UHFFFAOYSA-N 0.000 description 4
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 description 4
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- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
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- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 2
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- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
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- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
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Classifications
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Description
《位相差の測定》
配向膜用ポリイミド溶液を厚さ0.7mmのガラス基材にスピンコート法を用いて塗布し、100℃で10分乾燥した後、200℃で60分焼成することにより塗膜を得る。得られた塗膜を市販のラビング装置を用いてラビング処理する。
A1及びA2は各々独立して1,4-フェニレン基、1,4-シクロヘキシレン基、ピリジン-2,5-ジイル基、ピリミジン-2,5-ジイル基、ナフタレン-2,6-ジイル基、ナフタレン-1,4-ジイル基、テトラヒドロナフタレン-2,6-ジイル基、デカヒドロナフタレン-2,6-ジイル基又は1,3-ジオキサン-2,5-ジイル基を表すが、これらの基は無置換であるか又は1つ以上の置換基Lによって置換されても良く、Lはフッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、LはPL-(SpL-XL)kL-で表される基を表しても良く、ここでPLは重合性基を表し、好ましい重合性基は上記P0で定義したものと同一のものを表し、SpLは1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-COO-、-OCO-によって置換されても良い炭素原子数1から10の直鎖状アルキレン基又は単結合を表すが、SpLが複数存在する場合それらは同一であっても異なっていても良く、XLは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XLが複数存在する場合それらは同一であっても異なっていても良く(ただし、PL-(SpL-XL)kL-には-O-O-結合を含まない。)、kLは0から10の整数を表すが、化合物内にLが複数存在する場合それらは同一であっても異なっていても良く、置換基Lはフッ素原子、塩素原子、ペンタフルオロスルフラニル基、ニトロ基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、又は、任意の水素原子はフッ素原子に置換されても良く、1個の-CH2-又は隣接していない2個以上の-CH2-は各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-O-CO-O-、-CH=CH-、-CF=CF-又は-C≡C-から選択される基によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すことが好ましく、フッ素原子、塩素原子、又は、任意の水素原子はフッ素原子に置換されても良く、1個の-CH2-又は隣接していない2個以上の-CH2-は各々独立して-O-、-COO-又は-OCO-から選択される基によって置換されても良い炭素原子数1から12の直鎖状又は分岐状アルキル基を表すことがより好ましく、フッ素原子、塩素原子、又は、任意の水素原子はフッ素原子に置換されても良い炭素原子数1から12の直鎖状又は分岐状アルキル基若しくはアルコキシ基を表すことがさらに好ましく、フッ素原子、塩素原子、又は、炭素原子数1から8の直鎖アルキル基若しくは直鎖アルコキシ基を表すことが特に好ましい。
Z1及びZ2は各々独立して-O-、-S-、-OCH2-、-CH2O-、-CH2CH2-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-OCO-NH-、-NH-COO-、-NH-CO-NH-、-NH-O-、-O-NH-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-、-N=CH-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、Z1が複数存在する場合それらは同一であっても異なっていても良く、Z2が複数存在する場合それらは同一であっても異なっていても良く、
G1は芳香族炭化水素環又は芳香族複素環からなる群から選ばれる少なくとも1つの芳香族環を有する2価の基を表すが、G1で表される基中の芳香族環に含まれるπ電子の数は12以上であり、G1で表される基は無置換であるか又は1つ以上の置換基LGによって置換されても良く、置換基LGはフッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、LGはPLG-(SpLG-XLG)kLG-で表される基を表しても良く、ここでPLGは重合性基を表し、好ましい重合性基は上記P0で定義したものと同一のものを表し、SpLGは1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-COO-、-OCO-によって置換されても良い炭素原子数1から10の直鎖状アルキレン基又は単結合を表すが、SpLGが複数存在する場合それらは同一であっても異なっていても良く、XLGは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XLGが複数存在する場合それらは同一であっても異なっていても良く(ただし、PLG-(SpLG-XLG)kLG-には-O-O-結合を含まない。)、kLGは0から10の整数を表すが、化合物内にLGが複数存在する場合それらは同一であっても異なっていても良く、m1及びm2は各々独立して0から6の整数を表すが、m1+m2は0から6の整数を表す。)で表される化合物であることが好ましい。
W2は水素原子、又は、1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、W2は少なくとも1つの芳香族基を有する、炭素原子数2から30の基を表しても良いが、当該基は無置換であるか又は1つ以上の置換基LWによって置換されても良く、若しくは、W2はPW-(SpW-XW)kW-で表される基を表しても良く、ここでPWは重合性基を表し、SpWはスペーサー基又は単結合を表し、SpWが複数存在する場合それらは同一であっても異なっていても良く、XWは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XWが複数存在する場合それらは同一であっても異なっていても良く(ただし、PW-(SpW-XW)kW-には-O-O-結合を含まない。)、kWは0から10の整数を表し、
置換基LWはフッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、LWはPLW-(SpLW-XLW)kLW-で表される基を表しても良く、ここでPLWは重合性基を表し、好ましい重合性基は上記P0で定義したものと同一のものを表し、SpLWは1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-COO-、-OCO-によって置換されても良い炭素原子数1から10の直鎖状アルキレン基又は単結合を表すが、SpLWが複数存在する場合それらは同一であっても異なっていても良く、XLWは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XLWが複数存在する場合それらは同一であっても異なっていても良く(ただし、PLW-(SpLW-XLW)kLW-には-O-O-結合を含まない。)、kLWは0から10の整数を表すが、化合物内に置換基LWが複数存在する場合それらは同一であっても異なっていても良く、
Yは水素原子、フッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基又は1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくはYはPY-(SpY-XY)kY-で表される基を表しても良く、PYは重合性基を表し、好ましい重合性基は上記P0で定義したものと同一のものを表し、SpYは上述の1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-COO-、-OCO-によって置換されても良い炭素原子数1から10の直鎖状アルキレン基又は単結合を表し、SpYが複数存在する場合それらは同一であっても異なっていても良く、XYは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XYが複数存在する場合それらは同一であっても異なっていても良く(ただし、PY-(SpY-XY)kY-には-O-O-結合を含まない。)、kYは0から10の整数を表すが、W1及びW2は一緒になって環構造を形成しても良い。)から選ばれる基を表す。)から選ばれる基を表すことがより好ましい。溶媒への溶解性、合成の容易さの観点から、G1は上記の式(M-1)、式(M-3)、式(M-4)、式(M-7)、式(M-8)から選ばれる基を表すことがさらに好ましく、式(M-1)、式(M-7)、式(M-8)から選ばれる基を表すことがさらにより好ましく、式(M-7)、式(M-8)から選ばれる基を表すことが特に好ましい。
(実施例1)式(I-1)で表される化合物の製造
転移温度(昇温5℃/分):C 89-123 I
1H NMR(CDCl3)δ 1.05(t,3H),1.70(m,2H),2.70(t,2H),3.58-3.73(m,6H),3.75(t,2H),4.02(t,2H),4.27(t,2H),5.84(dd,1H),6.12(dd,1H),6.42(dd,1H),6.65(d,2H),7.00(d,2H),7.15-7.45(m,5H),7.51-7.70(m,5H),7.78(dd,1H),8.17(s,1H),11.7(s,1H)ppm.
LCMS:694[M+1]
(実施例2)式(I-2)で表される化合物の製造
転移温度(昇温5℃/分):C 75-108 N 180 I
1H NMR(CDCl3)δ 0.94(t,3H),1.10(m,2H),1.25(m,2H),1.29-1.57(m,11H),1.80-2.08(m,6H),2.30(m,2H),2.54(m,1H),3.67-3.78(m,6H),3.85(t,2H),4.11(t,2H),4.32(t,2H),5.84(dd,1H),6.15(dd,1H),6.40(dd,1H),6.82-7.00(m,4H),7.08-7.60(m,4H),7.65-8.10(m,3H)、8.40(s,1H)、11.6(s,1H)ppm.
LCMS:826[M+1]
(実施例3)式(I-3)で表される化合物の製造
転移温度(昇温5℃/分):C 131 I
1H NMR(CDCl3)δ 0.88-0.94(m,6H),1.10(m,2H),1.22-1.52(m,13H),1.72(m,6H),1.94(t,4H),2.32(m,4H),2.53-2.62(m,3H),3.69-3.77(m,6H),3.86(t,2H),4.12(t,2H),4.27-4.34(m,4H),5.83(dd,1H),6.16(dd,1H),6.43(dd,1H),6.91(d,2H),6.97-7.02(m,3H),7.16(t,1H),7.23(dd,1H),7.33(t,1H),6.66-7.72(m,3H),7.90(d,1H)ppm.
LCMS:910[M+1]
(実施例4)式(I-4)で表される化合物の製造
転移温度(昇温5℃/分):C 90 Sm 218 N 265 I
1H NMR(CDCl3)δ 0.88(m,6H),1.01-1.19(m,8H),1.32-1.45(m,6H),1.71-1.76(m,6H),1.88-1.99(m,3H),2.17(m,12H),2.31(m,4H),2.53(m,2H),2.67(m,1H),3.70-3.76(m,6H),3.85(t,2H),4.11(t,2H),4.31(m,4H),5.82(d,2H),6.15(q,2H),6.43(d,2H),6.92(m,5H),7.14-7.26(m,2H),7.33(t,1H),7.68(m,3H),7.88(s,1H)ppm.
(実施例5)式(I-5)で表される化合物の製造
転移温度(昇温5℃/分):C 77 S 90 N 109 I
1H NMR(CDCl3)δ 0.89(t,3H),1.20-1.35(m,10H),1.61-1.69(m,6H),1.78(m,2H),1.90(m,2H),2.07(t,4H),2.23(d,4H),2.50(m,2H),3.69-3.76(m,12H),3.83-3.87(m,8H),4.11(t,4H),4.32(t,6H),5.82(d,2H),6.15(q,2H),6.42(d,2H),6.83-6.98(m,10H),7.13(t,1H),7.32(t,1H),7.53(t,1H),7.66(t,2H),8.13(s,1H)ppm.
(実施例6)式(I-6)で表される化合物の製造
転移温度(昇温5℃/分):C 85 N 128 I
1H NMR(CDCl3)δ 1.22-1.28(m,4H),1.44-1.47(m,8H),1.60-1.82(m,12H),1.90(m,2H),2.07(t,4H),2.24(d,4H),2.53(m,2H),3.30(s,3H),3.50(t,2H),3.66(t,2H),3.85-3.89(m,6H),3.93(t,4H),4.17(t,4H),4.53(t,2H),5.82(d,2H),6.13(q,2H),6.40(d,2H),6.83-6.90(m,6H),6.95-6.98(m,4H),7.14(t,1H),7.32(t,1H),7.52(t,1H),7.67(t,2H),8.33(s,1H)ppm.
(実施例7)式(I-7)で表される化合物の製造
転移温度(昇温5℃/分):C 106 N 125 I
1H NMR(CDCl3)δ 0.92(t,3H),1.11(q,2H),1.25(m,2H),1.36(m,2H),1.48(m,4H),1.68-1.81(m,12H),1.93(t,4H),2.32(m,3H),2.58(m,2H),2.71(m,1H),3.30(s,3H),3.48(m,2H),3.62(m,2H),3.85(t,2H),3.94(t,2H),4.17(t,2H),4.47(t,2H),5.82(d,2H),6.12(q,2H),6.40(d,2H),6.87(d,2H),6.96(m,3H),7.16(t,1H),7.22(m,1H),7.33(t,1H),7.70(q,2H),7.88(d,1H),8.01(s,1H)ppm.
(実施例8)式(I-8)で表される化合物の製造
転移温度(昇温5℃/分):C 89-95 N 145 I
1H NMR(CDCl3)δ 1.24(m,4H),1.65(m,4H),1.91(m,2H),2.05-2.25(m,12H),2.55(m,2H),3.30(s,3H),3.51(m,2H),3.67(m,2H),3.84-3.89(m,6H),4.05(t,4H),4.36(t,4H),4.54(t,2H),5.84(dd,2H),6.13(dd,2H),6.41(dd,2H),6.84-6.89(m,6H),6.97-7.00(m,4H),7.14(t,1H),7.33(t,1H),7.52(d,1H),7.67(dd,2H),8.34(s,1H)ppm.
LCMS:1076[M+1]
(実施例9)式(I-9)で表される化合物の製造
転移温度(昇温5℃/分)C 71 N 115 I
1H NMR(CDCl3)δ 1.19-1.29(m,4H),1.41-1.82(m,22H),1.91(m,2H),2.08(m,4H),2.24(m,4H),2.53(m,2H),3.62(m,3H),3.67(m,2H),3.84-3.90(m,5H),3.94(t,4H),4.15-4.19(m,6H),4.53(t,2H),5.76(dd,1H),5.82(dd,2H),6.08(dd,1H),6.12(dd,2H),6.37(dd,1H),6.40(dd,2H),6.84-6.90(m,6H),6.95-6.98(m,4H),7.14(t,1H),7.32(t,1H),7.53(d,1H),7.65(d,1H),7.69(d,1H),8.34(s,1H)ppm.
LCMS:1244[M+1]
(実施例10)式(I-10)で表される化合物の製造
転移温度(昇温5℃/分、降温5℃/分):C 101-105(N 82)I
1H NMR(CDCl3)δ 0.92(t,3H),1.08-1.91(m,26H),2.06(d,2H),2.24(d,2H),2.51(m,2H),3.30(s,3H),3.51(dd,2H),3.67(dd,2H),3.87(quin,4H),3.94(t,2H),4.17(t,2H),4.54(t,2H),5.82(dd,1H),6.12(dd,1H),6.40(dd,1H),6.86(m,3H),6.97(m,2H),7.16(m,2H),7.32(t,1H),7.65(d,1H),7.70(d,1H),7.82(d,1H),8.36(s,1H)ppm.
(実施例11)式(I-11)で表される化合物の製造
転移温度(昇温5℃/分):C 67-100 I
1H NMR(CDCl3)δ 1.00(t,3H),1.28(m,2H),1.45-1.81(m,12H),1.97(br,1H),2.13(m,2H),2.26(m,2H),2.57(tt,1H),2.65(t,2H),3.27(s,3H),3.37(m,2H),3.50(m,2H),3.70(t,2H),3.95(q,4H),4.17(t,2H),4.33(t,2H),5.82(dd,1H),6.12(dd,1H),6.40(dd,1H),6.87(d,2H),6.98(m,3H),7.15(t,1H),7.25(m,5H),7.32(t,1H),7.64(m,2H),7.69(d,1H),7.91(s,1H)ppm.
(実施例12)式(I-12)で表される化合物の製造
LCMS:1153[M+1]
(実施例13)式(I-13)で表される化合物の製造
LCMS:1088[M+1]
(実施例14)式(I-14)で表される化合物の製造
LCMS:1259[M+1]
(実施例15)式(I-15)で表される化合物の製造
LCMS:1222[M+1]
(実施例16)式(I-16)で表される化合物の製造
LCMS:1188[M+1]
(実施例17)式(I-17)で表される化合物の製造
1H NMR(CDCl3)δ 0.92(t,3H),1.05-1.83(m,32H),1.93(t,5H),2.33(m,4H),2.55(m,2H),2.71(m、1H),3.30(s,3H),3.62(m,2H),3.85(t,2H),3.94(t,2H),4.17(t,2H),4.48(t,2H),5.82(dd,1H),6.12(dd,1H),6.40(dd,1H),6.88(d,2H),6.99(m,3H),7.17(t,1H),7.23(dd,1H),7.34(t,1H),7.66(d,1H),7.71(d,1H),7.89(d,1H),8.02(s,1H)ppm.
LCMS:978[M+1]
実施例1から実施例17と同様の方法及び公知の方法を用いて、上述の式(I-18)から式(I-99)で表される化合物を製造した。
(実施例18~34、比較例1~3)
実施例1から実施例17記載の式(I-1)から式(I-17)で表される化合物及び特許文献1記載の化合物(R-1)、特許文献2記載の化合物(R-2)、特許文献3記載の化合物(R-3)を評価対象の化合物とした。
(実施例35~51、比較例4~6)
配向膜用ポリイミド溶液をシクロオレフィンポリマー基材にスピンコート法を用いて塗布し、60℃で10分乾燥した後、100℃で60分焼成することにより塗膜を得た。得られた塗膜をラビング処理した。ラビング処理は、市販のラビング装置を用いて行った。
分類0:いずれの基盤目にもはがれがない。
分類1:カットの交差点における塗膜の小さなはがれが確認される(5%未満)。
分類2:塗膜がカットの線に沿って、交差点においてはがれている(5%以上15%未満)。
分類3:塗膜がカットの線に沿って部分的、全面的にはがれている(15%以上35%未満)。
分類4:塗膜がカットの線に沿って部分的、全面的に大きくはがれを生じている(35%以上65%未満)。
分類5:分類4以上(65%以上)。
Claims (6)
- 一般式(I)
R2は水素原子、フッ素原子、塩素原子、若しくは、炭素原子数1から12の直鎖アルキル基又は直鎖アルコキシ基を表し、
A1及びA2は式(A-1)から式(A-4)
Z1及びZ2は各々独立して-OCH2-、-CH2O-、-COO-、-OCO-又は単結合を表すが、Z1が複数存在する場合それらは同一であっても異なっていても良く、Z2が複数存在する場合それらは同一であっても異なっていても良く、
G1は下記の一般式(M-7)又は一般式(M-8)
W2は水素原子、若しくは、炭素原子数1から20の直鎖状又は分岐状アルキル基を表し、
Yは水素原子を表し、
m1は1又は2の整数を表し、m2は1の整数を表す。)で表される重合性低波長分散性又は重合性逆波長分散性化合物。 - 請求項1に記載の化合物を含有する組成物。
- 請求項1に記載の化合物を含有する液晶組成物。
- 請求項2又は請求項3に記載の組成物を用いた重合体。
- 請求項4記載の重合体を用いた光学異方体。
- 請求項1に記載の化合物を用いた樹脂、樹脂添加剤、オイル、フィルター、接着剤、粘着剤、油脂、インキ、医薬品、化粧品、洗剤、建築材料、包装材、液晶材料、有機EL材料、有機半導体材料、電子材料、表示素子、電子デバイス、通信機器、自動車部品、航空機部品、機械部品、農薬及び食品並びにそれらを使用した製品。
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JPWO2017098988A1 (ja) | 2018-01-25 |
CN108368070B (zh) | 2023-04-28 |
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JP6624696B2 (ja) | 2019-12-25 |
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