JP5376272B2 - 末端環構造にラテラル置換基を有する重合性化合物 - Google Patents
末端環構造にラテラル置換基を有する重合性化合物 Download PDFInfo
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- JP5376272B2 JP5376272B2 JP2013510938A JP2013510938A JP5376272B2 JP 5376272 B2 JP5376272 B2 JP 5376272B2 JP 2013510938 A JP2013510938 A JP 2013510938A JP 2013510938 A JP2013510938 A JP 2013510938A JP 5376272 B2 JP5376272 B2 JP 5376272B2
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- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003232 pyrogallols Chemical class 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
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- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/10—Esters
- C08F22/12—Esters of phenols or saturated alcohols
- C08F22/20—Esters containing oxygen in addition to the carboxy oxygen
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- C07C69/78—Benzoic acid esters
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- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
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- C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
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- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
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- C09K19/3814—Polyethers
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- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
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- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
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- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/13363—Birefringent elements, e.g. for optical compensation
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- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
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- C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
- C09K2019/325—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a tetrahydronaphthalene, e.g. -2,6-diyl (tetralin)
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- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3411—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a three-membered ring
- C09K2019/3413—Three-membered member ring with oxygen(s), e.g. oxirane in fused, bridged or spiro ring systems
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- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3416—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a four-membered ring, e.g. oxetane
Description
(製法1)下記化合物(S6)の製造
(製法2)下記化合物(S11)の製造
(製法3)下記化合物(S16)の製造
(製法4)下記化合物(S18)の製造
(製法5)下記化合物(S24)の製造
(製法6)下記化合物(S29)の製造
(実施例1) 式(I−1)で表される化合物の製造
(式(I−1)で表される化合物の物性値)
1H NMR(CDCl3)δ 2.19〜2.25(m,5H),2.34(s,3H),4.17(t,2H),4.39(t,2H),5.85(dd,1H),6.14(dd,1H),6.42(dd,1H),6.98〜7.08(m,5H),7.36(d,2H),8.16(d,2H),8.29(d,2H)ppm.
13C NMR(CDCl3)δ 16.1,20.8,28.5,61.1,64.7,113.1,114.3,121.3,121.6,122.0,127.0,127.5,128.2,129.8,131.0,131.7,131.8,132.4,135.6,147.2,155.2,163.3,164.2,164.3,166.1ppm.
LRMS(EI)m/z 474(100).
(実施例2) 式(I−2)で表される化合物の製造
(式(I−2)で表される化合物の物性値)
1H NMR(CDCl3)δ 1.45〜1.57(m,4H),1.73(quin,2H),1.85(quin,2H),2.19(s,3H),2.34(s,3H),4.06(t,2H),4.18(t,2H),5.82(dd,1H),6.12(dd,1H),6.41(dd,1H),6.97〜7.08(m,5H),7.36(d,2H),8.15(d,2H),8.29(d,2H)ppm.
13C NMR(CDCl3)δ 16.1,20.8,25.6,25.7,28.5,28.9,64.4,68.1,114.3,121.0,121.6,122.0,126.9,127.2,127.5,128.5,129.8,130.5,131.7,131.8,132.4,135.6,147.2,155.2,163.7,164.3,164.3,166.3ppm.
LRMS(EI)m/z 516(100).
(実施例3) 式(I−3)で表される化合物の製造
(式(I−3)で表される化合物の物性値)
1H NMR(CDCl3)δ 2.20〜2.26(m,5H),2.35(s,3H),4.18(t,2H),4.40(t,2H),5.85(dd,1H),6.14(dd,1H),6.43(dd,1H),7.01(d,2H),7.07(s,2H),7.11(s,1H),7.46(dd,1H),7.77(d,1H),7.93(d,1H),8.06(d,1H),8.20(d,2H),8.24(dd,1H),8.82(d,1H)ppm.
13C NMR(CDCl3)δ 16.2,20.8,28.5,61.1,64.7,114.3,118.8,121.6,121.6,122.5,126.2,126.6,127.5,128.1,128.2,129.8,130.4,131.0,131.6,131.8,132.4,135.7,136.4,147.3,150.8,163.2,164.7,165.0,166.1ppm.
LRMS(EI)m/z 524(100).
(実施例4) 式(I−4)で表される化合物の製造
(式(I−4)で表される化合物の物性値)
1H NMR(CDCl3)δ 1.45〜1.56(m,4H),1.73(quin,2H),1.86(quin,2H),2.23(s,3H),2.35(s,3H),4.07(t,2H),4.19(t,2H),5.82(dd,1H),6.13(dd,1H),6.41(dd,1H),7.00(dd,2H),7.06(s,2H),7.11(s,1H),7.46(dd,1H),7.77(d,1H),7.93(d,1H),8.06(d,1H),8.19(d,2H),8.23(dd,1H),8.81(s,1H)ppm.
13C NMR(CDCl3)δ 16.2,20.8,25.7,25.7,28.5,28.9,64.4,68.1,114.3,118.8,121.2,121.6,122.5,126.2,126.6,127.5,128.1,128.5,129.8,130.4,130.5,131.0,131.6,131.8,132.4,135.7,136.4,147.3,150.9,163.6,164.8,165.0,166.3ppm.
LRMS(EI)m/z 566(100).
(実施例5) 式(I−7)で表される化合物の製造
(式(I−7)で表される化合物の物性値)
1H NMR(CDCl3)δ 2.22(s,3H),2.25(quin,2H),2.34(s,3H),4.23(t,2H),4.42(t,2H),5.85(dd,1H),6.15(dd,1H),6.43(dd,1H),7.03〜7.09(m,3H),7.22(dd,2H),7.80(d,1H),7.89(d,1H),8.17(dd,1H),8.71(s,1H)ppm.
13C NMR(CDCl3)δ 16.2,20.8,28.5,61.3,64.5,106.4,119.9,121.7,124.5,126.2,127.0,127.5,127.9,128.3,129.9,130.9,131.0,131.5,131.7,135.5,137.4,147.4,158.9,165.3,166.1ppm.
LRMS(EI)m/z 418(100).
(実施例6) 式(I−5)で表される化合物の製造
(式(I−5)で表される化合物の物性値)
1H NMR(CDCl3)δ 2.20〜2.26(m,7H),2.35(s,3H),4.18(t,2H),4.40(t,2H),5.85(dd,1H),6.14(dd,1H),6.43(dd,1H),7.01(d,2H),7.07(s,2H),7.11(s,1H),7.46(dd,1H),7.77(d,1H),8.06(d,1H),8.20(d,2H),8.24(dd,1H),8.82(d,1H)ppm.
13C NMR(CDCl3)δ 16.2,20.8,28.5,61.1,61.5,64.7,114.3,118.8,121.6,121.6,122.5,126.2,126.6,127.5,128.1,128.2,129.8,130.4,131.0,131.8,132.4,135.7,136.4,147.3,150.8,163.2,164.7,165.0,166.1ppm.
LRMS(EI)m/z 538(100).
(実施例7) 式(I−11)で表される化合物の製造
(式(I−11)で表される化合物の物性値)
1H NMR(CDCl3)δ 2.20〜2.26(m,5H),2.35(s,3H),4.18(t,2H),4.40(t,2H),5.86(dd,1H),6.15(dd,1H),6.43(dd,1H),7.01(d,2H),7.09(d,3H),7.49(dd,1H),7.54(dd,1H),7.83(dd,2H),7.97(d,2H),8.10(dd,2H),8.21(d,2H),8.27(dd,2H),8.86(d,2H)ppm.
13C NMR(CDCl3)δ 16.2,20.9,28.5,61.1,64.7,114.4,118.9,118.9,121.6,121.7,122.4,122.7,126.2,126.3,126.8,127.6,128.2,128.2,128.3,129.9,130.5,130.6,131.0,131.1,131.2,131.7,131.8,131.9,132.5,135.7,136.5,136.6,147.3,150.8,151.1,163.3,164.7,165.1,165.1,166.1ppm.
LRMS(EI)m/z 694(100).
(実施例8) 式(I−13)で表される化合物の製造
(式(I−13)で表される化合物の物性値)
1H NMR(CDCl3)δ 1.29(m,4H),1.57(quin,2H),1.71(quin,2H),2.46(s,3H),2.65(s,3H),3.94(t,2H),4.15(t,2H),5.80(dd,1H),6.05(dd,1H),6.43(dd,1H),6.83(d,1H),6.92(d,2H),7.15(d,1H),7.24(d,1H),7.43(d,1H),7.39(s,1H),7.57(d,1H),8.03(d,2H),8.09(d,1H),8.22(s,1H)ppm.
13C NMR(CDCl3)δ 9.2,21.3,26.3,26.5,30.0,30.6,66.8,72.3,114.1,114.1,114.9,118.0,121.4,122.2,122.7,126.6,126.7,127.4,127.9,128.6,128.6,128.6,128.8,130.3,130.7,130.7,130.9,131.4,132.1,152.6,158.7,164.0,164.0,164.0,165.0ppm.
LRMS(EI)m/z 600(100).
(実施例9)
(式(I−14)で表される化合物の物性値)
1H NMR(CDCl3)δ 1.44−1.56(m,4H),1.73(quin,7.3Hz,2H),1.84(quin,7.3Hz,2H),2.21(s,3H),2.34(s,3H),4.02(t,6.5Hz,2H),4.18(t,6.5Hz,2H),5.82(dd,1.4,10.4Hz,1H),6.13(dd,10.4,17.4Hz,1H),6.41(dd,1.6,17.3Hz,1H),6.98−7.09(m,5H),7.59(d,8.9Hz,2H),7.69(d,8.9Hz,2H),8.25(d,8.11Hz,2H)ppm.
13C NMR(CDCl3)δ 16.2,20.9,25.7,25.7,28.6,29.1,64.5,67.9,114.9,121.7,126.6,127.5,128.4,128.6,129.9,130.6,130.6,130.7,131.8,132.1,135.6,145.9,147.3,159.4,165.0,166.3ppm.
LRMS(EI)m/z 472(100).
(実施例10〜14、比較例1〜5)
実施例1から実施例5に記載の本願発明の化合物(I−1)から化合物(I−4)、化合物(I−7)、化合物(I−9)、EP1786887B1号公報記載の比較化合物1、比較化合物2及びGB2280445A号公報記載の比較化合物3の物性値を下記表1に記載した。
次に、本願組成物である実施例10から実施例14並びに比較組成物である比較例1から比較例5のそれぞれの重合性液晶組成物98%に光重合開始剤イルガキュア907(チバスペシャリティーケミカル社製)を2%添加した後シクロヘキサノンに溶解させ、ポリイミド付きガラスにスピンコートし、これに高圧水銀ランプを用いて4mW/cm2の紫外線を120秒間照射し、本願重合体である実施例15から実施例19及び比較重合体である比較例6から比較例10を得た。得られた重合体のヘイズ値と外観を評価した。ヘイズ値は下記式
ヘイズ(%)=Td/Tt×100
(式中、Tdは拡散透過率、Ttは全光線透過率を表す。)で表され、測定にはヘイズ測定装置(日本電色工業株式会社製NHD2000)を用い、基板上5カ所について測定を行い、その平均をとった。また、目視によって重合体上にムラ等が無く全体に均一であれば◎、ムラが見られる場合は△とした。
Claims (7)
- 一般式(I)
- 一般式(I)においてA3が、L1がフッ素原子、塩素原子又は炭素原子数1から4のアルキル基若しくはアルコキシ基を表し、さらにベンゼン環又はナフタレン環上の水素原子がフッ素原子、塩素原子又は炭素原子数1から4のアルキル基若しくはアルコキシ基によって置換されていても良い式(A3−1)又は式(A3−5)で表される請求項1記載の重合性化合物。
- 一般式(I)においてA3が、L1がフッ素原子、塩素原子、CH3基又はCH3O基を表し、さらにベンゼン環又はナフタレン環上の水素原子がフッ素原子、塩素原子、CH3基又はCH3O基によって置換されていても良い式(A3−1)又は式(A3−5)で表される請求項1又は2記載の重合性化合物。
- 一般式(I)においてZ1及びZ2が、各々独立して−COO−、−OCO−、−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−又は−CH2−OCO−で表わされる請求項1から3のいずれか一項に記載の重合性化合物。
- 請求項1から4のいずれか一項に記載の重合性化合物を含有する重合性液晶組成物。
- 請求項5記載の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。
- 請求項6記載の重合体を用いた光学異方体。
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JP6090514B1 (ja) * | 2016-05-18 | 2017-03-08 | 日本ゼオン株式会社 | 重合性化合物の製造方法 |
JP2017206494A (ja) * | 2017-02-08 | 2017-11-24 | 日本ゼオン株式会社 | ハロゲン化体および混合物 |
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US9469810B2 (en) * | 2011-11-30 | 2016-10-18 | Dic Corporation | Polymerizable liquid crystal composition and thin film using same |
JP5522319B1 (ja) * | 2013-04-05 | 2014-06-18 | Dic株式会社 | 組成物の製造方法 |
KR20170106953A (ko) * | 2015-01-16 | 2017-09-22 | 디아이씨 가부시끼가이샤 | 중합성 화합물 및 광학 이방체 |
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US11370740B2 (en) * | 2016-03-10 | 2022-06-28 | Dic Corporation | Method for producing ester group-containing compound |
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