JP6308415B2 - 重合性化合物及びそれを用いた液晶組成物 - Google Patents
重合性化合物及びそれを用いた液晶組成物 Download PDFInfo
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- JP6308415B2 JP6308415B2 JP2018502192A JP2018502192A JP6308415B2 JP 6308415 B2 JP6308415 B2 JP 6308415B2 JP 2018502192 A JP2018502192 A JP 2018502192A JP 2018502192 A JP2018502192 A JP 2018502192A JP 6308415 B2 JP6308415 B2 JP 6308415B2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 11
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 5
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- 150000002367 halogens Chemical class 0.000 claims description 4
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- BDLXTDLGTWNUFM-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]ethanol Chemical compound CC(C)(C)OCCO BDLXTDLGTWNUFM-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- 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
- 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
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- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3004—Cy-Cy
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- G—PHYSICS
- 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
- 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
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
-
- G—PHYSICS
- 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
- 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
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/13378—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation
- G02F1/133788—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation by light irradiation, e.g. linearly polarised light photo-polymerisation
Description
また、本発明の他の課題は、フイルム基板に重合性の液晶組成物を塗布し硬化させた場合の密着性改善及び、PSA表示素子に用いた場合の組成物の保存安定性、及び表示特性、短いUV照射時間又は少ない照射エネルギーでポリマー化するUV反応性、未反応の重合物の残存量の低減を改善した液晶表示素子を提供することである。
R1及びR2はお互い独立して、水素原子又は以下の式(R−1)から式(R−15):
L1は、単結合、−OCH2−、−CH2O−、−CO−、−C2H4−、−COO−、−OCO−、−OCOOCH2−、−CH2OCOO−、−OCH2CH2O−、−CH=CRa−COO−、−CH=CRa−OCO−、−COO−CRa=CH−、−OCO−CRa=CH−、−COO−CRa=CH−COO−、−COO−CRa=CH−OCO−、−OCO−CRa=CH−COO−、−OCO−CRa=CH−OCO−、−COOC2H4−、−OCOC2H4−、−C2H4OCO−、−CH2OCO−、−COOCH2−、−OCOCH2−、−CH=CH−、−CF=CF−、−CF=CH−、−CH=CF−、−CF2O−、−OCF2−、−CF2CH2−、−CH2CF2−、−CF2CF2−又は−C≡C−を表し、 L2は、−C4H8−、−OCH2CH2O−、−CH=CRa−COO−、−CH=CRa−OCO−、−COO−CRa=CH−、−OCO−CRa=CH−、−COO−CRa=CH−COO−、−COO−CRa=CH−OCO−、−OCO−CRa=CH−COO−、−OCO−CRa=CH−OCO−、−COOC2H4−、−OCOC2H4−、−C2H4OCO−(式中、Raはそれぞれ独立して水素原子又は炭素原子数1〜4のアルキル基を表す。)を表し、
M1およびM2は、それぞれ独立して、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、1,3−ジオキサン−2,5−ジイル基、1,3,5−ベンゼントリイル基、1,3,4−ベンゼントリイル基又は1,3,4,5−ベンゼンテトライル基を表し、前記M1及びM2は、それぞれ独立して、アルキル基、ハロゲン化アルキル基、アルコキシ基、ハロゲン化アルコキシ基、ハロゲン、シアノ基又はニトロ基により置換されていても良く、
X1、X2およびX3は、それぞれ独立して、水素原子、炭素原子数1〜5のアルキル基、炭素原子数1〜5のハロゲン化アルキル基、炭素原子数1〜5のアルコキシ基、炭素原子数1〜5のハロゲン化アルコキシ基、ハロゲン原子、シアノ基又はニトロ基を表し、
mおよびnは、それぞれ互い独立して、0又は1の整数を表し、l及びoは1又は2を表す。)で表される重合性化合物である。
4‘−ベンジルオキシ−4−ヒドロキシ−3−メトキシビフェニルとエチレングリコールモノターシャリーブチルエーテルとのトリフェニルホスフィン、ジイソプロピルアゾジカルボン酸との光延反応により、ビフェノール誘導体(S−1)を得て、更にパラジウムカーボンを用いた接触水素還元を行った後、塩化メタクリロイルとのエステル化反応によりメタクリル酸誘導体(S−2)を得る。次いでトリフルオロ酢酸により、ターシャリーブチル基を脱離させてエタノールに変換したメタクリル酸誘導体(S−3)を得る。
4−ブロモ−4‘−オキシテトラヒドロキシピラニル−3−プロポキシビフェニルとメタクリル酸ターシャリーブチルとのヘック反応によりビフェニル誘導体(S−4)を得て、更にテトラヒドロピラニル基を塩酸/テトラヒドフラン溶液で除去した後、メタクリル酸とのエステル化反応でメタクリル誘導体(S−5)を得る。次いで、蟻酸/ジクロロメタンによりターシャリーブチル基を除去した後、4−メタクリロイルオキシフェノールとのエステル化で目的物の化合物(I−12)を得る。
4‘−ベンジルオキシ−4−ヒドロキシ−3−プロポキシビフェニルとエチレングリコールモノターシャリーブチルエーテルとのトリフェニルホスフィン、ジイソプロピルアゾジカルボン酸との光延反応により、ビフェノール誘導体(S−6)を得て、更にパラジウムカーボンを用いた接触水素還元を行った後、6−クロロヘキシルアクリレートとのエーテル化反応によりアクリル酸誘導体(S−7)を得る。
4−{(4‘−ベンジルオキシ)−3−メトキシ−(1,1’−ビフェニル)−4−イル}ブタナール と4−ベンジルオキシフェニルマグネシウムブロミドとの反応によりビフェニル誘導体(S−9)を得る。更にp−トルエンスルホン酸を用いた脱水反応によりアルケン化合物(S−10)を得た後、パラジウムカーボンを用いた接触水素還元によりベンジル基及びアルケン部を還元してヒドロキシビフェニル誘導体(S−11)得る。
一般式(II)で表される化合物について、L11及びL12はお互い独立して、単結合、−O−、−COO−又は−OCO−が好ましく、M11及びM12はお互い独立して、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−ジイル基又はナフタレン−2,6−ジイル基が好ましい。
本願発明の重合性化合物は、偏向板、位相差板などに用いられる光学補償フイルムを作成する際の構成成分として有効であり、重合性化合物で液晶分子の配向を制御するPSA(Polymer Sustained Alignment)型液晶表示装置、PSVA(Polymer Stabilised Vertical Alignment)型液晶表示装置にも有効である。またOCB(Optically Compensated Birefringence)−LCD及びIPS−LCD(インプレーンスイッチング液晶表示素子)にも使用可能である。当該液晶表示装置の駆動方式としては、アクティブ駆動及びパッシブ駆動が可能であり、AM−LCD(アクティブマトリックス液晶表示素子)、TN(ネマチック液晶表示素子)及びSTN−LCD(超ねじれネマチック液晶表示素子)に有用であり、AM−LCDに特に有用である。
本発明の重合性化合物を用いたPSA、PS−VA、PS−IPS及びPS−OCB液晶組成物の場合は、一般式(I)で表される重合性化合物を少なくとも1種を含有するが、1種〜5種含有することが好ましく、1種〜3種含有することが特に好ましい。また、一般式(I)で表される重合性化合物の含有率は、少ないと非重合性液晶化合物に対する配向規制力が弱くなり、多すぎると重合時の必要エネルギーが上昇し、重合せず残存してしまう重合性化合物の量が増してしまうため、下限値は0.01質量%であることが好ましく、0.03質量%であることがより好ましく、上限値は5.0質量%であることが好ましく、1.0質量%であることがより好ましい。
撹拌装置、冷却器、及び温度計を備えた反応容器に4−ベンジルオキシフェニルホウ酸 35g(155ミリモル)、4−ブロモ−2−メトキシフェノール 30.5g(150ミリモル)、炭酸カリウム 32g(232ミリモル)、テトラキストリフェニルホスフィンパラジウム 1.8g、テトラヒドロフラン200ml、純水100mlを仕込み、70℃で5時間反応させた。反応終了後、冷却し、10%塩酸を加えた後、酢酸エチルにより目的物を抽出した。有機層を水、飽和食塩水で洗浄し、溶媒を留去した。その後、トルエンによる分散洗浄、アルミナカラムによる精製を行い式(1)で表される化合物 37gを得た。
1H−NMR(溶媒:重クロロホルム):δ: 2.12(s,6H),3.85(s,3H),5.77(s,2H),6.38(s,2H),7.11−7.25(m,5H),7.54−7.58(m,2H)
13C−NMR(溶媒:重クロロホルム):δ:17.9,55.8,113.2,121.5,122.3,123.5,128.1,129.4,137.2,143.8,150.3,151.4,166.4
赤外吸収スペクトル(IR)(KBr):1760,1652−1622,809cm−1
融点:101℃
(実施例2)
撹拌装置、冷却器、及び温度計を備えた反応容器に4−ベンジルオキシ−3−メトキシフェニルホウ酸 39g(150ミリモル)、4−ブロモ−2−メトキシフェノール 28.5g(140ミリモル)、炭酸カリウム 32g(232ミリモル)、テトラキストリフェニルホスフィンパラジウム 1.6g、テトラヒドロフラン200ml、純水100mlを仕込み、70℃で5時間反応させた。反応終了後、冷却し、10%塩酸を加えた後、酢酸エチルにより目的物を抽出した。有機層を水、飽和食塩水で洗浄し、溶媒を留去した。その後、トルエンによる分散洗浄、アルミナカラムによる精製を行い式(4)で表される化合物 40gを得た。
1H−NMR(溶媒:重クロロホルム):δ: 2.12(s,6H),3.87(s,6H),5.77(s,2H),6.39(s,2H),7.11(s,6H)
13C−NMR(溶媒:重クロロホルム):δ:17.9,55.8,113.1,121.8,123.5,128.1,137.2,143.8,150.3,151.4,166.4
赤外吸収スペクトル(IR)(KBr):1760,1652−1622,809cm−1
融点:125℃
(実施例3)
撹拌装置、冷却器、及び温度計を備えた反応容器に実施例(1)で合成した式(1)の化合物 27.5g(90ミリモル)、エチレングリコールモノターシャリーブチルエーテル 12g(107ミリモル)、トリフェニルホスフィン 35g(134ミリモル)、ジクロロメタン 300mlを仕込み、反応容器を5℃に冷却した。その後、ジアゾカルボン酸ジイソプロピル(DIAD)22g(107ミリモル)を滴下した。滴下終了後、室温で5時間撹拌して反応を終了させた。反応終了後、ジクロロメタン 200mlを加え、純水、飽和食塩水で有機層を洗浄した。溶媒を留去した後、シリカゲルカラムによる精製により(7)で表される化合物32gを得た。
1H−NMR(溶媒:重クロロホルム):δ: 2.06(d,6H),3.96(s,3H),4.39(dd,4H),5.74(dd,2H),6.33(dd,2H),6.38−6.94(m,2H),7.03−7.05(m,3H),7.09−7.11(m,2H),7.12−7.19(m,2H),7.52−7.53(m,2H)
13C−NMR(溶媒:重クロロホルム):δ:17.8,56.1,68.9,69.2,111.2,113.6,114.8,118.0,122.1,128.2,129.5,135.3,136.2,137.6,138.3,142.9,149.5,150.4,166.0
赤外吸収スペクトル(IR)(KBr):1760,1652−1622,809cm−1
融点:141℃
(実施例4)
撹拌装置、冷却器、及び温度計を備えた反応容器に2−(4−ブロモフェノキシ)テトラヒドロピラン 40g(155ミリモル)、4−ヒドロキシフェニルホウ酸 21g(155ミリモル)、炭酸カリウム 32g(232ミリモル)、テトラキストリフェニルホスフィンパラジウム 1.8g、テトラヒドロフラン200ml、純水100mlを仕込み、70℃で5時間反応させた。反応終了後、冷却し、10%塩酸を加えた後、酢酸エチルにより目的物を抽出した。有機層を水、飽和食塩水で洗浄し、溶媒を留去した。その後、トルエンによる分散洗浄、アルミナカラムによる精製を行い式(12)1で表される化合物 27gを得た。
1H−NMR(溶媒:重クロロホルム):δ: 2.73(t,3H),2.85(t,3H),3.93(s,3H),5.74−5.78(m,2H),6.10−6.13(m,2H),6.24−6.31(m,2H),6.91−7.05(m,3H),7.12−7.15(m,3H),7.34−7.39(m,2H),7.71(d,2H),
13C−NMR(溶媒:重クロロホルム):δ:30.5,33.7,55.8,113.4,121.8,122.0,123.0,123.3,123.4,123.9,126.6,127.1,127.4,128.0,133.1,135.7,138.8,140.5,141.9,145.6,150.2,150.7,163.3,165.7,170.1,172.3
赤外吸収スペクトル(IR)(KBr):1760,1652−1622,809cm−1
(実施例5)
撹拌装置、冷却器、及び温度計を備えた反応容器に4−ブロモ−2−メトキシフェノール 31g(155ミリモル)、4−ベンジルオキシ−2−フルオロフェニルホウ酸 38g(155ミリモル)、炭酸カリウム 32g(232ミリモル)、テトラキストリフェニルホスフィンパラジウム 1.8g、テトラヒドロフラン300ml、純水100mlを仕込み、70℃で5時間反応させた。反応終了後、冷却し、10%塩酸を加えた後、酢酸エチルにより目的物を抽出した。有機層を水、飽和食塩水で洗浄し、溶媒を留去した。その後、トルエンによる分散洗浄、アルミナカラムによる精製を行い式(16)1で表される化合物 39gを得た。
1H−NMR(溶媒:重クロロホルム):δ: 2.08(s,6H),3.86(s,3H),5.77(s,2H),6.38(s,2H),6,99−7.02(m,2H),7.09−7.15(m,3H),7.41(m,1H)
13C−NMR(溶媒:重クロロホルム):δ:17.9,55.8,110.2,113.4,117.7,121.8,123.5,125.8,128.1,134.3,135.3,137.3,151.1,159.1,166.0,
赤外吸収スペクトル(IR)(KBr):1760,1652−1622,809cm−1
融点:81℃
(実施例6)
撹拌装置、冷却器、及び温度計を備えた反応容器に4‘−ベンゾイルオキシー3,5−ジフロロ−3’−メトキシ(1,1‘−ビフェニル)−4−オール 30.8g(90ミリモル)、エチレングリコールモノターシャリーブチルエーテル 12g(107ミリモル)、トリフェニルホスフィン 35g(134ミリモル)、ジクロロメタン 300mlを仕込み、反応容器を5℃に冷却した。その後、ジアゾカルボン酸ジイソプロピル(DIAD)22g(107ミリモル)を滴下した。滴下終了後、室温で5時間撹拌して反応を終了させた。反応終了後、ジクロロメタン 200mlを加え、純水、飽和食塩水で有機層を洗浄した。溶媒を留去した後、シリカゲルカラムによる精製により(19)で表される化合物33gを得た。
1H−NMR(溶媒:重クロロホルム):δ: 2.05(s,3H),2.08(s,3H),3.94(s,3H),4.28−4.29(m,2H),4.50−4.52(m,2H),5.77(d,2H),6.38(d,2H),6,91−6.94(m,2H),7.03−7.13(m,6H)
13C−NMR(溶媒:重クロロホルム):δ:17.9,55.8,68.9,113.4,116.8,117.8,121.8,123.1,128.6,131.5,137.3,144.5,144.6,152.6,153.8,154.3,166.3
赤外吸収スペクトル(IR)(KBr):1760,1652−1622,809cm−1
融点:81℃
(実施例7)
以下に示す組成の重合性液晶組成物(組成物1)を調製した。
以下に示す組成の重合性液晶組成物(組成物3)を調製した。
以下に示す組成の重合性液晶組成物(組成物4)を調製した。
下記に示す化合物を含有した液晶組成物LC−1を調製した。構成する化合物及び含有する比率は以下の通りである。
下記に示す化合物を含有した液晶組成物LC−1を調製した。構成する化合物及び含有する比率は以下の通りである。
下記に示す化合物を含有した液晶組成物LC−2を調製した。構成する化合物及び含有する比率は以下の通りである。
上記液晶組成物LC−1に上記に示す式(16)で表される化合物0.3%添加した。この重合性液晶組成物は−10℃で1週間保管しても析出は見られず、保存安定性に優れていた。この組成物を3.5μmの配向処理を施したポリイミド付きFFSガラスセル注入し、紫外線を5J照射後、FFSガラスセルから液晶組成物を抽出し、高速液体クロマトグラフィーで残存モノマーを分析した結果、モノマーが0.1%検出された。
Claims (9)
- 一般式(I):
S 2 は、炭素原子数1〜12個のアルキレン基及び単結合からなる群から選択される少なくとも1種の連結基であり、該アルキレン基中の1個の−CH 2 −又は隣接していない2個以上の−CH 2 −は、−O−、−COO−又は−OCOO−に置き換えられても良く、
R1及びR2は、それぞれ独立して、水素原子又は以下の式(R−1)から式(R−15):
L1は、単結合、−OCH2−、−CH2O−、−CO−、−C2H4−、−COO−、−OCO−、−OCOOCH2−、−CH2OCOO−、−OCH2CH2O−、−CH=CRa−COO−、−CH=CRa−OCO−、−COO−CRa=CH−、−OCO−CRa=CH−、−COO−CRa=CH−COO−、−COO−CRa=CH−OCO−、−OCO−CRa=CH−COO−、−OCO−CRa=CH−OCO−、−COOC2H4−、−OCOC2H4−、−C2H4OCO−、−CH2OCO−、−COOCH2−、−OCOCH2−、−CH=CH−、−CF=CF−、−CF=CH−、−CH=CF−、−CF2O−、−OCF2−、−CF2CH2−、−CH2CF2−、−CF2CF2−又は−C≡C−、(式中、Raはそれぞれ独立して水素原子又は炭素原子数1〜4のアルキル基を表す)を表し、 L2は、−C4H8−、−OCH2CH2O−、−CH=CRa−COO−、−CH=CRa−OCO−、−COO−CRa=CH−、−OCO−CRa=CH−、−COO−CRa=CH−COO−、−COO−CRa=CH−OCO−、−OCO−CRa=CH−COO−、−OCO−CRa=CH−OCO−、−COOC2H4−、−OCOC2H4−又は−C2H4OCO−、(式中、Raはそれぞれ独立して水素原子又は炭素原子数1〜4のアルキル基を表す)を表し、
M1およびM2は、それぞれ独立して、
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、1,3−ジオキサン−2,5−ジイル基、1,3,5−ベンゼントリイル基、1,3,4−ベンゼントリイル基又は1,3,4,5−ベンゼンテトライル基を表すが、前記M1及びM2は、それぞれ独立して、アルキル基、ハロゲン化アルキル基、アルコキシ基、ハロゲン化アルコキシ基、ハロゲン、シアノ基又はニトロ基により置換されていても良く、
X1 は、水素原子、炭素原子数1〜5のアルキル基、炭素原子数1〜5のハロゲン化アルキル基、炭素原子数1〜5のアルコキシ基、炭素原子数1〜5のハロゲン化アルコキシ基、シアノ基又はニトロ基を表し、
X2およびX3は、それぞれ独立して、水素原子、炭素原子数1〜5のアルキル基、炭素原子数1〜5のハロゲン化アルキル基、炭素原子数1〜5のアルコキシ基、炭素原子数1〜5のハロゲン化アルコキシ基、ハロゲン原子、シアノ基又はニトロ基を表し、
mおよびnは、それぞれ独立して、0又は1の整数を表し、l及びoは、それぞれ独立して、1又は2の整数を表す。)で表される重合性化合物。 - 前記一般式(I)中、L1が−OCH2−、−CH2O−、−COO−、−OCO−、−C2H4−、−C≡C−、−OCF2−、−CF2O−又は単結合を表し、
M1及びM2が、それぞれ独立して、1,4−シクロヘキシレン基、1,4−フェニレン基又はナフタレン−2,6−ジイル基、1,3,5−ベンゼントリイル基、1,3,4−ベンゼントリイル基又は1,3,4,5−ベンゼンテトライル基を表すが、前記M1及びM2は、それぞれ独立して、アルキル基、ハロゲン化アルキル基、アルコキシ基、ハロゲン化アルコキシ基、ハロゲン、シアノ基又はニトロ基により置換されていても良く、mが1を表す、請求項1記載の重合性化合物。 - 前記一般式(I)中、mが0を表す請求項1記載の重合性化合物。
- 前記一般式(I)中、M2が、1,3,5−ベンゼントリイル基、1,3,4−ベンゼントリイル基または1,3,4,5−ベンゼンテトライル基を表し、nが1を表す、請求項1記載の重合性化合物。
- 請求項1〜4のいずれか1項に記載の重合性化合物を含有する重合性組成物。
- 液晶相を呈する、請求項5記載の重合性組成物。
- 一対の基板を有する液晶表示素子に使用する前記重合性化合物を含有する重合性化合物含有液晶組成物であって、
前記一対の基板間における前記重合性化合物含有液晶組成物中の前記重合性化合物由来の重合体により液晶配向能が付与されることを特徴とする、請求項1〜6に記載の重合性化合物含有液晶組成物。 - 請求項5〜6のいずれか1項に記載の重合性液晶組成物を重合することにより形成される光学異方体。
- 前記重合性化合物含有液晶組成物を使用し、前記重合性化合物含有液晶組成物中の前記重合性化合物を重合することにより液晶配向能を付与した、請求項7記載の液晶表示素子。
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