JP6217999B2 - 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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- JP6217999B2 JP6217999B2 JP2016549178A JP2016549178A JP6217999B2 JP 6217999 B2 JP6217999 B2 JP 6217999B2 JP 2016549178 A JP2016549178 A JP 2016549178A JP 2016549178 A JP2016549178 A JP 2016549178A JP 6217999 B2 JP6217999 B2 JP 6217999B2
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Classifications
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- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
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Description
Sはスペーサー基又は単結合を表すが、S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、
X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、X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、P−(S−X)k−には−O−O−結合を含まない。)、
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Lによって置換されても良く、A1及び/又はA2が複数現れる場合は各々同一であっても異なっていても良く、
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、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、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、
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及び/又はZ2が複数現れる場合は各々同一であっても異なっていても良く、
Mは下記の式(M−1)から式(M−8)
R1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、シアノ基、ニトロ基、イソシアノ基、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−、−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、
Gは下記の式(G−1)又は式(G−2)
W1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の基を表すが、当該基は無置換であるか又は1つ以上のLWによって置換されても良く、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いが、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、
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、また、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し、
kは0から8の整数を表し、m1及びm2は各々独立して0から5の整数を表すが、m1+m2は1から5の整数を表す。)で表される化合物を提供し、併せて当該化合物を含有する重合性組成物、重合性液晶組成物、当該重合性液晶組成物を重合させることにより得られる重合体及び当該重合体を用いた光学異方体を提供する。
X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、X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い(ただし、P−(S−X)k−には−O−O−結合を含まない。)。また、原料の入手容易さ及び合成の容易さの観点から、複数存在する場合は各々同一であっても異なっていても良く、各々独立して−O−、−S−、−OCH2−、−CH2O−、−COO−、−OCO−、−CO−S−、−S−CO−、−O−CO−O−、−CO−NH−、−NH−CO−、−COO−CH2CH2−、−OCO−CH2CH2−、−CH2CH2−COO−、−CH2CH2−OCO−又は単結合を表すことが好ましく、各々独立して−O−、−OCH2−、−CH2O−、−COO−、−OCO−、−COO−CH2CH2−、−OCO−CH2CH2−、−CH2CH2−COO−、−CH2CH2−OCO−又は単結合を表すことがより好ましく、複数存在する場合は各々同一であっても異なっていても良く、各々独立して−O−、−COO−、−OCO−又は単結合を表すことが特に好ましい。
Gは下記の式(G−1)又は式(G−2)
(製法1)下記式(S−9)で表される化合物の製造
式(S−1)で表される化合物をホルミル化することによって、式(S−2)で表される化合物を得ることができる。反応例として例えば塩化マグネシウム及び塩基存在下パラホルムアルデヒドと反応させる方法が挙げられる。塩基としては例えばトリエチルアミン等が使用可能である。
(製法2)下記式(S−15)で表される化合物の製造
式(S−10)で表される化合物を式(S−11)で表される化合物と反応させることによって、式(S−12)で表される化合物を得ることができる。反応例として例えば金属触媒及び塩基存在下、クロスカップリングさせる方法が挙げられる。金属触媒としては例えば、[1,1’−ビス(ジフェニルホスフィノ)フェロセン]パラジウム(II)ジクロリド、酢酸パラジウム(II)、テトラキス(トリフェニルホスフィン)パラジウム(0)が挙げられる。塩基としては例えばトリエチルアミン等が挙げられる。反応条件としては例えばMetal−Catalyzed Cross−Coupling Reactions(Armin de Meijere、Francois Diedrich共著、Wiley−VCH)、Palladium Reagents and Catalysts:New Perspectives for the 21st Century(Jiro Tsuji著、Wiley & Sons,Ltd.)、Cross−Coupling Reactions:A Practical Guide(Topics in Current Chemistry)(S.L.Buchwald、K.Fugami、T.Hiyama、M.Kosugi、M.Miura、N.Miyaura、A.R.Muci、M.Nomura、E.Shirakawa、K.Tamao著、Springer)等の文献に記載の方法が挙げられる。
(製法3)下記式(S−25)で表される化合物の製造
式(S−16)で表される化合物のヒドロキシル基を保護基(PG)によって保護する。保護基(PG)としては、脱保護工程に至るまで安定に保護しうるものであれば特に制限は無いが、例えば、GREENE’S PROTECTIVE GROUPS IN ORGANIC SYNTHESIS((Fourth Edition)、PETER G.M.WUTS、THEODORA W.GREENE共著、A John Wiley & Sons,Inc.,Publication)等に挙げられている保護基(PG)が好ましい。保護基の具体例としてはテトラヒドロピラニル基が挙げられる。
本願発明の化合物を含有する重合性液晶組成物には、当該組成物の液晶性を大きく損なわない程度に、液晶性を示さない重合性化合物を添加することも可能である。具体的には、この技術分野で高分子形成性モノマーあるいは高分子形成性オリゴマーとして認識される化合物であれば特に制限なく使用可能である。具体例として例えば「光硬化技術データブック、材料編(モノマー,オリゴマー,光重合開始剤)」(市村國宏、加藤清視監修、テクノネット社)記載のものが挙げられる。
(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 105 N 150 I
1H NMR(CDCl3)δ 0.93(t,3H),1.10(q,2H),1.25(m,2H),1.37(m,3H),1.46−1.59(m,6H),1.74(quin,2H),1.81−1.98(m,6H),2.56(m,1H),4.03(t,2H),4.19(t,2H),5.83(dd,1H),6.13(dd,1H),6.41(dd,1H),6.87(d,2H),7.08(t,1H),7.12(d,1H),7.20(t,1H),7.28(dd,1H),7.45(dd,1H),7.58(d,1H),7.84(s,1H),8.06(m,3H)ppm.
MS(m/z):668[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 62 N 95 poly
1H NMR(CDCl3)δ 0.89(t,3H),1.33(m,4H),1.43−1.57(m,2H),1.61(quin,2H),1.73(quin,2H),1.85(quin,2H),2.59(t,2H),2.97(m,4H),4.03(t,2H),4.19(m,2H),5.83(dd,1H),6.13(dd,1H),6.41(dd,1H),6.87(d,2H),7.04−7.29(m,8H),7.44(d,1H),7.58(d,1H),7.85(s,1H),8.05(m,3H)ppm.
MS(m/z):718[M++1]
(実施例3)式(I−3)で表される化合物の製造
MS(m/z):794[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 156 N 173 I
1H NMR(CDCl3)δ 1.02(t,3H),1.40−1.92(m,12H),4.00(br,2H),4.09(t,2H),4.18(t,2H),5.82(dd,1H),6.13(dd,1H),6.41(dd,1H),6.64−6.13(m,14H),8.19(d,2H)ppm.
MS(m/z):736[M++1]
(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 147 N 153 I
1H NMR(CDCl3)δ 0.93(t,3H),1.37(m,4H),1.46−1.59(m,4H),1.63−1.78(m,4H),1.86(quin,2H),2.68(t,2H),4.07(t,2H),4.19(t,2H),5.84(dd,1H),6.14(dd,1H),6.42(dd,1H),7.00(d,2H),7.09(t,1H),7.12(d,1H),7.19(t,1H),7.23−7.33(m,3H),7.45(d,1H),7.61(d,1H),7.80(d,1H),8.07(s,1H),8.14−8.23(m,4H)ppm.
MS(m/z):734[M++1]
(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 79 N 137 I
1H NMR(CDCl3)δ 1.01(t,3H),1.48(m,4H),1.69−1.79(m,6H),2.67(t,2H),3.95(m,2H),4.18(t,2H),5.83(dd,1H),6.13(dd,1H),6.41(dd,1H),6.83(m,2H),7.03−7.68(m,10H),7.97−8.30(m,4H)ppm.
MS(m/z):662[M++1]
(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 79 N 112 I
1H NMR(CDCl3)δ 0.96(t,3H),1.43−1.78(m,8H),1.87(quin,2H),2.60(t,2H),4.08(t,2H),4.20(t,2H),5.83(dd,1H),6.13(dd,1H),6.42(dd,1H),7.01(d,2H),7.09(t,1H),7.17−7.29(m,7H),7.37(d,1H),7.60(d,1H),7.91(s,2H),8.21(d,2H)ppm.
MS(m/z):662[M++1]
(実施例8)式(I−8)で表される化合物の製造
MS(m/z):838[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 178 N 180 I
1H NMR(CDCl3)δ 1.44−1.60(m,4H),1.74(quin,2H),1.86(quin,2H),3.89(s,3H),4.07(t,2H),4.20(t,2H),5.83(dd,1H),6.14(dd,1H),6.42(dd,1H),6.99(m,3H),7.09(t,1H),7.13(d,1H),7.19(t,1H),7.27(d,2H),7.44(d,1H),7.54(d,1H),7.60(d,1H),8.03(s,1H),8.17(d,4H)ppm.
MS(m/z):694[M++1]
(実施例10)式(I−10)で表される化合物の製造
MS(m/z):837[M++1]
(実施例11)式(I−11)で表される化合物の製造
IR:3060−3030,2975−2920,1725,1630,1200,1160,1130,750,690cm−1.
MS(m/z):829[M++1]
(実施例12)式(I−12)で表される化合物の製造
MS(m/z):631[M++1]
(実施例13)式(I−13)で表される化合物の製造
MS(m/z):1204[M++1]
(実施例14)式(I−14)で表される化合物の製造
MS(m/z):1034[M++1]
(実施例15)式(I−15)で表される化合物の製造
MS(m/z):705[M++1]
(実施例16)式(I−106)で表される化合物の製造
転移温度(昇温5℃/分):C 169 N 178 I
1H NMR(CDCl3)δ 1.43(t,3H),1.47−1.60(m,4H),1.75(quin,2H),1.87(m,2H),3.99(q,2H),4.08(t,2H),4.20(t,2H),5.83(dd,1H),6.14(dd,1H),6.42(dd,1H),6.85(d,2H),7.01(d,2H),7.08(t,1H),7.14(t,1H),7.20(t,3H),7.25(dd,1H),7.35(d,1H),7.60(d,1H),7.90(d,1H),7.94(s,1H)8.21(d,2H)ppm.
MS(m/z):664[M++1]
(実施例17)式(I−107)で表される化合物の製造
転移温度(昇温5℃/分):C 98 N 157 I
1H NMR(CDCl3)δ 0.94(t,3H),1.31−1.76(m,12H),2.66(t,2H),3.89(t,2H),4.12(t,2H),5.80(dd,1H),6.13(dd,1H),6.41(dd,1H),6.50−8.20(m,16H)ppm.
MS(m/z):700[M++1]
(実施例18)式(I−108)で表される化合物の製造
転移温度(昇温5℃/分):C 164 I
1H NMR(DMSO−d6)δ 0.94(t,3H),1.65(q,2H),2.15(t,2H),2.63(t,2H),4.22(t,2H),4.30(t,2H),5.96(d,1H),6.20(q,1H),6.36(d,1H),7.10(t,1H),7.18(d,2H),7.28(t,1H),7.35(d,2H),7.52(d,2H),7.63(d,2H),7.23(t,2H),8.15(t,3H),8.25(s,1H)ppm.
MS(m/z):620[M++1]
(実施例19)式(I−109)で表される化合物の製造
転移温度(昇温5℃/分):C 155 N 158 I
1H NMR(CDCl3)δ 1.02(t,3H),1.73(q,3H),1.86(m,4H),2.68(t,2H),3.96(m,2H),4.24(m,2H),5.85(d,1H),6.14(dd,1H),6.43(d,1H),6.80(m,2H),7.08−7.33(m,5H),7.44(m,1H),7.59(m,4H),8.01(m,2H),8.23(m,2H)ppm.
MS(m/z):634[M++1]
(実施例20)式(I−110)で表される化合物の製造
転移温度(昇温5℃/分):C 154 I
1H NMR(CDCl3)δ 0.95(tt,3H),1.63(m,2H),2.24(quin,2H),2.59(m,2H),4.19(t,2H),4.41(t,2H),5.85(dd,1H),6.14(dd,1H),6.43(dd,1H),7.02(d,2H),7.09−7.28(m,8H),7.37(d,1H),7.60(d,1H),7.91(m,2H),8.22(d,2H)ppm.
MS(m/z):620[M++1]
(実施例21)式(I−111)で表される化合物の製造
転移温度(昇温5℃/分):C 146 N 149 I
1H NMR(CDCl3)δ 0.95(t,3H),1.63(m,2H),1.93(m,4H),2.58(t,2H),4.12(t,2H),4.28(t,2H),5.85(dd,1H),6.14(dd,1H),6.43(dd,1H),7.01(d,2H),7.07−7.29(m,8H),7.36(d,1H),7.60(d,1H),7.91(m,2H),8.21(d,2H)ppm.
MS(m/z):634[M++1]
(実施例22)式(I−112)で表される化合物の製造
転移温度(昇温5℃/分):C 117 N 220 I
1H NMR(CDCl3)δ 0.92(t,3H),1.07(q,2H),1.24−2.06(m,27H),2.35(m,2H),2.55(t,1H),3.95(t,2H),4.18(t,2H),5.83(dd,1H),6.13(dd,1H),6.42(dd,1H),6.88(d,2H),6.98(m,3H),7.19−7.26(m,2H),7.35(m,1H),7.51(m,1H),7.68(m,1H),7.89(m,1H),8.08(m,1H)ppm.
MS(m/z):794[M++1]
(実施例23)式(I−113)で表される化合物の製造
転移温度(昇温5℃/分):C 90 S 156 N
1H NMR(CDCl3)δ 0.92(t,3H),1.09(m,2H),1.31(m,13H),1.48(m,6H),1.74(t,3H),1.81(t,3H),1.93(m,6H),2.54(t,1H),2.72(t,1H),3.94(t,2H),4.18(t,2H),5.81(d,1H),6.13(q,1H),6.41(d,1H),6.41(d,1H),6.88(d,2H),6.96(d,2H),7.20(t,1H),7.26(d,1H),7.45(d,1H),7.57(d,1H),7.84(s,1H),8.07(d,3H)ppm.
MS(m/z):822[M++1]
(実施例24)式(I−114)で表される化合物の製造
転移温度(昇温、降温5℃/分):C 128 (N 80) I
1H NMR(CDCl3)δ 0.92(t,3H),1.07(m,2H),1.20−1.50(m,11H),1.66(quin,2H),1.78(quin,2H),1.89(m,4H),2.51(tt,1H),2.73(t,2H),2.91(t,2H),3.95(t,2H),4.14(t,2H),5.81(dd,1H),6.12(dd,1H),6.39(dd,1H),6.85(d,2H),6.93(d,1H),7.09(d,2H),7.14(t,1H),7.21(dd,1H),7.33(t,1H),7.54(d,1H),7.58(s,1H),7.66(d,1H),7.80(d,1H)ppm.
MS(m/z):696[M++1]
(実施例25)式(I−115)で表される化合物の製造
転移温度(昇温、降温5℃/分):C 128 (N 80) I
1H NMR(CDCl3)δ 1.00(t,3H),1.47−1.60(m,4H),1.73(m,4H),1.87(quin,2H),2.67(t,2H),3.55(s,3H),4.08(t,2H),4.20(t,2H),5.84(dd,1H),6.14(dd,1H),6.42(dd,1H),7.02(d,2H),7.13(t,1H),7.25−7.33(m,6H),7.39(d,1H),7.62(dd,2H),7.69(s,1H),7.93(d,1H),8.22(d,2H)ppm.
MS(m/z):696[M++1]
(実施例26)式(I−116)で表される化合物の製造
転移温度(昇温5℃/分):C 64−77 N >220 I
1H NMR(CDCl3)δ 0.92(t,3H),1.07(q,2H),1.23(m,2H),1.37(m,3H),1.48−1.60(m,6H),1.74(quin,2H),1.83−1.90(m,4H),1.97(d,2H),2.56(tt,1H),4.07(t,2H),4.19(t,2H),5.83(dd,1H),6.13(dd,1H),6.42(dd,1H),7.00(d,2H),7.11(q,1H),7.12(d,1H),7.19−7.31(m,4H),7.46(d,1H),7.61(d,1H),7.85(d,1H),8.09(s,1H),8.17(m,4H)ppm.
MS(m/z):788[M++1]
(実施例27)式(I−117)で表される化合物の製造
転移温度(昇温5℃/分):C 147−156 N 173 I
1H NMR(CDCl3)δ 0.92(t,3H),1.11(q,2H),1.25(m,2H),1.37−1.55(m,9H),1.71(m,6H),1.78(m,2H),1.94(m,4H),2.33(m,4H),2.56(m,2H),2.70(m,1H),3.72(s,3H),3.94(t,2H),4.17(t,2H),5.82(dd,1H),6.13(dd,1H),6.40(dd,1H),6.88(d,2H),6.98(m,3H),7.17(t,1H),7.24(dd,1H),7.35(t,1H),7.66−7.72(m,3H),7.88(d,1H)ppm.
MS(m/z):808[M++1]
(実施例28)式(I−118)で表される化合物の製造
転移温度(昇温5℃/分):C 117−122 N 146 I
1H NMR(CDCl3)δ 0.91(m,6H),1.10(q,2H),1.23−1.56(m,18H),1.68−1.81(m,9H),1.94(t,4H),2.32(m,4H),2.56−2.70(m,3H),3.94(t,2H),4.18(t,2H),4.29(t,2H),5.82(dd,1H),6.13(dd,1H),6.40(dd,1H),6.89(d,2H),6.99(m,3H),7.16(t,1H),7.23(dd,1H),7.34(t,1H),7.66−7.72(m,3H),7.90(d,1H)ppm.
MS(m/z):878[M++1]
(実施例29)式(I−119)で表される化合物の製造
転移温度(昇温5℃/分):C 190 N 260 I
1H NMR(CDCl3)δ 0.89(t,1H),1.05(t,2H),1.31(q,2H),1.50(m,6H),1.74,(m,15H),2.54(t,1H),4.03(t,2H),4.19(t,2H),5.81(d,1H),6.13(q,1H),6.41(d,1H),6.43(d,1H),7.09(d,2H),7.11(d,2H),7.20(t,1H),7.26(d,1H),7.45(d,1H),7.57(d,1H),7.84(s,1H),8.07(d,3H)ppm.
MS(m/z):750[M++1]
(実施例30)式(I−120)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.
MS(m/z):978[M++1]
(実施例31)式(I−122)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32)式(I−126)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),1.05−1.83(m,22H),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.
(実施例33)式(I−127)で表される化合物の製造
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1から実施例33と同様の方法、公知の方法に準拠した方法を用いて、式(I−16)から式(I−105)、式(I−121)、式(I−123)から式(I−125)、式(I−128)で表される化合物を製造した。
(実施例34〜66、比較例1〜3)
実施例1から実施例33記載の式(I−1)から式(I−15)、式(I−106)から式(I−120)、式(I−122)、式(I−126)、式(I−127)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)並びに特許文献3記載の化合物(R−3)を評価対象の化合物とした。
(実施例67〜99、比較例4〜6)
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。
Claims (8)
- 一般式(I)
下記の式(P−1)から式(P−20)
SIはスペーサー基又は単結合を表すが、SI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、
前記スペーサー基が各々独立して、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−、−OCO−O−、−CO−NH−、−NH−CO−、−CH=CH−又は−C≡C−に置き換えられても良い炭素原子数1から20のアルキレン基を表し、
X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、X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、P−(S I −X)k−には−O−O−結合を含まない。)、
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Lによって置換されても良く、A1及び/又はA2が複数現れる場合は各々同一であっても異なっていても良く、
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、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、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、
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及び/又はZ2が複数現れる場合は各々同一であっても異なっていても良く、存在するZ1及びZ2の少なくとも1つは−O−、−S−、−OCH2−、−CH2O−、−CH2CH2−、−CO−、−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−又は単結合を表し、
Mは下記の式(M−1)から式(M−8)
R1は水素原子、フッ素原子、塩素原子、シアノ基、又は、1個の−CH2−若しくは隣接していない2個以上の−CH2−が各々独立して−O−、−COO−、−OCO−若しくは−O−CO−O−によって置換されても良い炭素原子数1から12の直鎖状若しく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、
Gは下記の式(G−1)又は式(G−2)
W1は炭素原子数2から30の下記の式(W−1)から式(W−19)
で表される少なくとも1つの芳香族基を表すが、当該基は無置換であるか又は1つ以上のLWによって置換されても良く、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いが、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、又はW 1 は下記の式(W−20)
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又はシアノ基に置換されても良く、若しくは、W2は炭素原子数2から30の式(W−1)から式(W−19)で表される少なくとも1つの芳香族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、また、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し、
kは0から8の整数を表し、m1及びm2は各々独立して0から5の整数を表すが、m1+m2は1から5の整数を表す。)で表される化合物。 - 一般式(I)において、W1及びW2に含まれるπ電子の総数が4から24である、請求項1に記載の化合物。
- 請求項1から請求項3のいずれか一項に記載の化合物を含有する組成物。
- 請求項1から請求項3のいずれか一項に記載の化合物を含有する液晶組成物。
- 請求項4又は請求項5に記載の組成物を重合することにより得られる重合体。
- 請求項6記載の重合体を用いた光学異方体。
- 請求項1から請求項3いずれか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、自動車部品、航空機部品、機械部品、農薬若しくは食品又はそれらのいずれかを使用した製品。
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