新型相邻长支链取代的聚酰亚胺液晶垂直取向剂的合成及其用于液晶显示元件的性能表现
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摘要
报道了一类新型相邻柔性长支链聚酰亚胺液晶垂直取向剂的合成,并考察其用于液晶显示元件的性能表现。首先,以2,3,4-三氟硝基苯、4-(4-庚基环己基)-苯酚、邻苯二甲酰亚胺钾盐等原料合成了含有相邻柔性长支链结构的新型功能性对苯二胺(L-14),通过核磁共振波谱(NMR)和高压液相色质联用(HPLC-MS)对目标产物进行结构表征。用1,2,3,4-环丁烷四甲酸二酐(CBDA)、对苯二胺(PDA)和L-14制备了一类PDA与L-14不同比例的聚酰亚胺液晶垂直取向剂,并对以该聚酰亚胺膜作为液晶取向层制得的液晶显示元件开展了预倾角、液晶定向时间、陡度、对比度等性能测试。结果表明,基于该新型聚酰亚胺液晶垂直取向膜的液晶显示元件耐磨性能强、液晶定向时间短、取向性能优良、显示画面清晰。
The synthesis of a new polyimide liquid crystal vertical alignment agent substituted with adjacent double long side chains was reported,and its performance for liquid crystal display elements was investigated.First,2,3,4-trifluoronitrobenzene,4-(4-heptylcyclohexyl)-phenol,phthalimide potassium salt and other raw materials were used to synthesize a functional diamine(L-14)substituted with adjacent double long side chains.The diamine L-14 was characterized by NMR and HPLC-MS.Then a kind of polyimide liquid crystal vertical alignment agents were prepared using 1,2,3,4-cyclobutanetetracarboxylic dianhydride(CBDA),p-phenylenediamine(PDA)and L-14 with variant ratio of L-14/PDA.The liquid crystal display elements prepared with thus obtained polyimine film as the aligning layer were subjected to performance tests such as pretilt angle,liquid crystal aligning time,steepness,and contrast.The results show that the liquid crystal display elements based on the newly synthesized polyimide liquid crystal vertical aligning film possess strong abrasion resistance,short liquid crystal aligning time,excellent orientation performance,and clear display image.
The synthesis of a new polyimide liquid crystal vertical alignment agent substituted with adjacent double long side chains was reported,and its performance for liquid crystal display elements was investigated.First,2,3,4-trifluoronitrobenzene,4-(4-heptylcyclohexyl)-phenol,phthalimide potassium salt and other raw materials were used to synthesize a functional diamine(L-14)substituted with adjacent double long side chains.The diamine L-14 was characterized by NMR and HPLC-MS.Then a kind of polyimide liquid crystal vertical alignment agents were prepared using 1,2,3,4-cyclobutanetetracarboxylic dianhydride(CBDA),p-phenylenediamine(PDA)and L-14 with variant ratio of L-14/PDA.The liquid crystal display elements prepared with thus obtained polyimine film as the aligning layer were subjected to performance tests such as pretilt angle,liquid crystal aligning time,steepness,and contrast.The results show that the liquid crystal display elements based on the newly synthesized polyimide liquid crystal vertical aligning film possess strong abrasion resistance,short liquid crystal aligning time,excellent orientation performance,and clear display image.
引文
[1]日本学术振兴会第142委员会.液晶器件手册[M].黄锡珉,黄辉光,李之熔,译.北京:航空工业出版社,1992.Japan Society for the Promotion of Science,Committee 142.Handbook of Liquid Crystal Devices[M].Huang XM,Huang H G,Li Z R,trans.Beijing:Aviation Industry Press,1992.(in Chinese)
[2]杨正华,李悦生,丁孟贤,等.TN-LCD用聚酰亚胺取向排列剂[J].液晶与显示,1995,3(2):77-81.YANG Z H,LI Y S,DING M X,et al.Polyimide as alignment agent of the twist nematic liquid crystals display device[J].Chinese Letters of Liquid Crystals and Displays,1995,3(2):77-81.(in Chinese)
[3]孙睿鹏,黄锡珉.液晶的表面排列机理[J].液晶与显示,1995,3(2):82-109.SUN R P,HUANG X M.Surface alignment mechanism of liquid crystals[J].Chinese Journal of Liquid Crystals and Displays,1995,3(2):82-109.(in Chinese)
[4]徐寿颐.液晶显示器用取向材料和封接材料[J].化工新型材料,1992(5):10-14.XU S Y.Orienting material and sealing material for liquid crystal display[J].New Chemical Materials,1992(5):10-14.(in Chinese)
[5]徐寿颐,张伟,石琳.聚酰亚胺取向材料表面排列性能的研究[J].功能材料,1995,26(1):87-90.XU S Y,ZHANG W,SHI L.Study on the surface orientation properties of the polyimide aligning agents[J].Journal of Functional Materials,1995,26(1):87-90.(in Chinese)
[6]LEE J B,LEE H K,PARK J C,et al.The structural effects on the pretilt angle of alignment materials with alkylcyclohexylbenzene as a side chain in polyimides[J].Molecular Crystals and Liquid Crystals,2005,439(1):161-172.
[7]CAI C,LIEN A,ANDRY P S,et al.Dry vertical alignment method for multi-domain homeotropic thin-filmtransistor liquid crystal displays[J].Japanese Journal of Applied Physics,2001,40(12):6913-6917.
[8]DAVID H,WANG Z H,SHEN M M,et al.Synthesis and properties of polyimides containing multiple alkyl side chains[J].Macromolecules,2007,40(4):889-900.
[9]LEE S W,KIM S I,PARK Y H,et al.Liquid-crystal alignment on the rubbed film surface of semi-flexible copolyimides containing n-alkyl side group[J].Molecular Crystals and Liquid Crystals Science and Technology.Section A.:Molecular Crystals and Liquid Crystals,2000,349(1):279-282.
[10]郭春桔,夏森林,孙振,等.侧链含稠环的新型聚酰亚胺液晶垂直取向剂的制备及表征[J].液晶与显示,2012,27(1):8-13.GUO C J,XIA S L,SUN Z,et al.Preparation and characterization of novel polyimide with thick ring in side chain for vertical alignment liquid crystals[J].Chinese Journal of Liquid Crystals and Displays,2012,27(1):8-13.(in Chinese)
[11]刘志杰,于奋飞,汪映寒.聚酰亚胺液晶垂直取向膜的制备与性质[J].液晶与显示,2007,22(5):524-528.LIU Z J,YU F F,WANG Y H.Preparation and properties of a novel polyimide liquid crystal vertical alignment layer[J].Chinese Journal of Liquid Crystals and Displays,2007,22(5):524-528.(in Chinese)
[12]SEO D S,ARAYA K,YOSHIDA N,et al.Effect of the polymer tilt angle for generation of pretilt angle in nematic liquid crystal on rubbed polyimide surfaces[J].Japanese Journal of Applied Physics,1995,34(4B):L503-L506.
[2]杨正华,李悦生,丁孟贤,等.TN-LCD用聚酰亚胺取向排列剂[J].液晶与显示,1995,3(2):77-81.YANG Z H,LI Y S,DING M X,et al.Polyimide as alignment agent of the twist nematic liquid crystals display device[J].Chinese Letters of Liquid Crystals and Displays,1995,3(2):77-81.(in Chinese)
[3]孙睿鹏,黄锡珉.液晶的表面排列机理[J].液晶与显示,1995,3(2):82-109.SUN R P,HUANG X M.Surface alignment mechanism of liquid crystals[J].Chinese Journal of Liquid Crystals and Displays,1995,3(2):82-109.(in Chinese)
[4]徐寿颐.液晶显示器用取向材料和封接材料[J].化工新型材料,1992(5):10-14.XU S Y.Orienting material and sealing material for liquid crystal display[J].New Chemical Materials,1992(5):10-14.(in Chinese)
[5]徐寿颐,张伟,石琳.聚酰亚胺取向材料表面排列性能的研究[J].功能材料,1995,26(1):87-90.XU S Y,ZHANG W,SHI L.Study on the surface orientation properties of the polyimide aligning agents[J].Journal of Functional Materials,1995,26(1):87-90.(in Chinese)
[6]LEE J B,LEE H K,PARK J C,et al.The structural effects on the pretilt angle of alignment materials with alkylcyclohexylbenzene as a side chain in polyimides[J].Molecular Crystals and Liquid Crystals,2005,439(1):161-172.
[7]CAI C,LIEN A,ANDRY P S,et al.Dry vertical alignment method for multi-domain homeotropic thin-filmtransistor liquid crystal displays[J].Japanese Journal of Applied Physics,2001,40(12):6913-6917.
[8]DAVID H,WANG Z H,SHEN M M,et al.Synthesis and properties of polyimides containing multiple alkyl side chains[J].Macromolecules,2007,40(4):889-900.
[9]LEE S W,KIM S I,PARK Y H,et al.Liquid-crystal alignment on the rubbed film surface of semi-flexible copolyimides containing n-alkyl side group[J].Molecular Crystals and Liquid Crystals Science and Technology.Section A.:Molecular Crystals and Liquid Crystals,2000,349(1):279-282.
[10]郭春桔,夏森林,孙振,等.侧链含稠环的新型聚酰亚胺液晶垂直取向剂的制备及表征[J].液晶与显示,2012,27(1):8-13.GUO C J,XIA S L,SUN Z,et al.Preparation and characterization of novel polyimide with thick ring in side chain for vertical alignment liquid crystals[J].Chinese Journal of Liquid Crystals and Displays,2012,27(1):8-13.(in Chinese)
[11]刘志杰,于奋飞,汪映寒.聚酰亚胺液晶垂直取向膜的制备与性质[J].液晶与显示,2007,22(5):524-528.LIU Z J,YU F F,WANG Y H.Preparation and properties of a novel polyimide liquid crystal vertical alignment layer[J].Chinese Journal of Liquid Crystals and Displays,2007,22(5):524-528.(in Chinese)
[12]SEO D S,ARAYA K,YOSHIDA N,et al.Effect of the polymer tilt angle for generation of pretilt angle in nematic liquid crystal on rubbed polyimide surfaces[J].Japanese Journal of Applied Physics,1995,34(4B):L503-L506.