JP4924865B2 - 重合性液晶化合物、重合性液晶組成物及びこれの重合体 - Google Patents
重合性液晶化合物、重合性液晶組成物及びこれの重合体 Download PDFInfo
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- JP4924865B2 JP4924865B2 JP2006012395A JP2006012395A JP4924865B2 JP 4924865 B2 JP4924865 B2 JP 4924865B2 JP 2006012395 A JP2006012395 A JP 2006012395A JP 2006012395 A JP2006012395 A JP 2006012395A JP 4924865 B2 JP4924865 B2 JP 4924865B2
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- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- JNTPTNNCGDAGEJ-UHFFFAOYSA-N 6-chlorohexan-1-ol Chemical compound OCCCCCCCl JNTPTNNCGDAGEJ-UHFFFAOYSA-N 0.000 description 2
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- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
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- SUSAZDLJYMQAEJ-UHFFFAOYSA-N 2-[4-(4-hydroxyphenyl)phenyl]acetic acid Chemical group C1=CC(CC(=O)O)=CC=C1C1=CC=C(O)C=C1 SUSAZDLJYMQAEJ-UHFFFAOYSA-N 0.000 description 1
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- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical class OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 1
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- JTGCXYYDAVPSFD-UHFFFAOYSA-N 4-(4-hydroxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(O)C=C1 JTGCXYYDAVPSFD-UHFFFAOYSA-N 0.000 description 1
- XGYITPJVLUVDJP-UHFFFAOYSA-N CCCCCCc(cc1)ccc1-c1ccc(C)cc1 Chemical compound CCCCCCc(cc1)ccc1-c1ccc(C)cc1 XGYITPJVLUVDJP-UHFFFAOYSA-N 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004696 Poly ether ether ketone Substances 0.000 description 1
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- 150000008062 acetophenones Chemical class 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
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- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
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- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 1
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Liquid Crystal Substances (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Liquid Crystal (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
一般式(I)は次に記載する一般式(Ia)
このような化合物の中でも耐熱性や耐久性の点から、一般式(I-2)、一般式(I-5)、一般式(I-6)、一般式(I-9)又は一般式(I-10)の化合物が好ましく、一般式(I-2)の化合物が特に好ましい。
本発明の化合物は、通常の有機合成で用いられる手法で合成することができる。例えば、以下のような合成例を挙げることができる。
(S-1)のアルコール誘導体を酸触媒下でアクリル酸と反応させて(S-2)を得る。(S-2)と(S-3)の2-(4-ヒドロキシフェニル)エタノールを炭酸カリウム等の塩基触媒を用いて反応させて(S-4)のフェネチルアルコール誘導体を得る。次に、(S-5)の4-ヒドロキシ-4’-カルボキシメチルビフェニルと(S-6)を反応させて(S-7)を得て、さらに加水分解して(S-8)を得る。さらに(S-8)を酸触媒下でアクリル酸と反応させて(S-9)を得る。最後に、(S-9)と(S-4)をジシクロヘキシルカルボジイミド等の縮合剤を用いて反応させて(S-10)のような本発明の化合物を合成することができる。
r、sはそれぞれ独立的に3〜6の整数が特に好ましい。
u、vは3〜18が好ましく、4〜16が好ましく、6〜12がさらに好ましい。
さらに本発明の重合性液晶組成物には、重合性官能基を有する化合物であって、液晶性を示さない化合物を添加することもできる。このような化合物としては、通常、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ものであれば特に制限なく使用することができるが、その添加量は組成物として液晶性を呈するように調整する必要がある。
また、電場によって配向状態を制御する場合には、電極層を有する基板を使用する。この場合、電極上に前述のポリイミド薄膜等の有機薄膜を形成するのが好ましい。
このような方法によって製造される本発明の重合体は、基板から剥離して単体で用いても、剥離せずに用いても良い。また、得られた重合体を積層しても、他の基板に貼り合わせて用いてもよい。
(実施例1)
重合性化合物の合成(1)
200mlの水に、水酸化ナトリウム8g、テトラブチルアンモニウムブロミド2.2g、4-(4-ヒドロキシフェニル)安息香酸42.8gを加えて撹拌し、50℃に加熱した。この反応液に、100mlのトルエンに溶解させた32.6gの6-クロロ-1-ヘキサノールを滴下し、14時間加熱還流させた。室温まで冷却後、反応液に5%塩酸水溶液を加えてpHを2〜3に調節し、結晶を析出させ、ろ取した。ろ取した結晶を水で洗浄し、更に風乾しての式(1)の粗生成物を64g得た。
ヘキサン475ml、6-クロロ-1-ヘキサノール63.2g、ヒドロキノン0.5g、p-トルエンスルホン酸4.4gの混合物を生成してくる水を留去しながら6時間還流させた。室温まで冷却後300mlのTHFを加え、飽和炭酸水素ナトリウム水溶液、ついで飽和塩化ナトリウム水溶液で洗浄した。有機層を水洗した後、有機溶媒を減圧留去して式(3)
2-(4-ヒドロキシフェニル)エチルアルコール200g、式(3)の化合物44g、炭酸カリウム32g、2,4-ジ-tertブチルフェノール0.4g、DMF200mlの混合物を80℃で16時間加熱撹拌した。室温まで冷却後、有機層を希塩酸水溶液、飽和塩化ナトリウム水溶液で洗浄後、有機溶媒を減圧留去して式(4)
(実施例2)
実施例1と同様の方法を用いて、式(6)
以下に示す組成の重合性液晶組成物(A)を調製した。重合性液晶組成物(A)は、一度、等方性液体相まで加熱してから冷却すると、75℃でネマチック相に相転移した。このネマチック相は室温においても保たれた。
(比較例1)
以下に示す組成の重合性液晶組成物(B)を調製した。重合性液晶組成物(A)は、一度、等方性液体相まで加熱してから冷却すると、72℃でネマチック相に相転移した。
(実施例6)
以下に示す組成の重合性液晶組成物(C)を調製した。
(比較例2)
以下に示す組成の重合性液晶組成物(D)を調製した。
Claims (4)
- 請求項1記載の重合性液晶化合物を含有し、ネマチック相またはスメクチックA相を呈することを特徴とする重合性液晶組成物。
- 請求項1記載の重合性液晶化合物、もしくは請求項2記載の重合性液晶組成物の重合体。
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