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研究生:徐敏華
研究生(外文):Miin-Hua Hsu
論文名稱:含丙烯酸酯及桂皮醇基之碟狀化合物之合成及其在光配向膜上之應用
論文名稱(外文):Synthesis of Discotic Compounds Containing Acrylate and Cinnamoyl Side Groups for Application of Liquid Crystal Photo Alignment Layers
指導教授:許千樹
指導教授(外文):Chain-Shu Hsu
學位類別:碩士
校院名稱:國立交通大學
系所名稱:應用化學系
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2002
畢業學年度:90
語文別:中文
論文頁數:59
中文關鍵詞:碟狀化合物光配向膜
外文關鍵詞:discoticphoto alignment
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本研究主要是探討不同的感光基團在配向膜上的應用;將合成出的含丙烯酸酯及桂皮醇基之碟狀分子與環氧基及香豆素之碟狀分子作比較,此四種配向材料塗佈在ITO玻璃後製成薄膜,經一次線性偏極紫外光照射後均能達到排列液晶之能力。討論其含不同感光基團之盤狀分子之熱穩定性及光穩定性,經線性偏極紫外光(LPUV)照射配向膜後所製成之液晶盒測量,其中,在兩種測量溫度下,所測得之結果可知,HTP11Cu之熱穩定性較佳。此四種材料以傾斜線性偏極紫外光照射後均得到小角度之預傾角,而所測得的扭轉錨定能均在10-6J/cm2左右,其所測得的驅動電壓皆在1.5V以下,此種結果可應用於薄膜電晶顯示器顯示器(TFT-LCD)上的潛力。
The goal of this study is to synthesize two discotic compounds containing acrylate (HTP6Ac) and cinnamoyl (HTP6Ci) side groups which are used for the application of photo-alignment layers in liquid crystal display (LCD). These compounds were coated on ITO glass substrates and irradiated with linearly polarized UV light (LPUV), and their photo-alignment capability was compared with that of their corresponding discotic compounds containing epoxy(HTP11Ep) and coumarin(HTP11Cu) side groups in terms of thermal stability, photo stability, pretilt angle and twist anchoring energy. For HTP6Ac and HTP6Ci films, they underwent photoaddition and 【2+2】 photodimerization reaction during UV exposure. The LC alignment direction is parallel to the polarization axis of LPUV. Among these four disc compounds, HTP11Cu film required the lowest exposure energy to achieve alignment and showed the highest thermal stability. Both discotic compounds are soluble in common organic solvents. When they are irradiated with a sigle oblique exposure of LPUV light, uniform alignment for a LC cell can be achieved. The pretilt angle is around 1° and the twist anchoring energy is about 10-6 J/cm2. The threshold voltages are below 1.5 V. These discotic compounds have potential application for the alignment materials of TFT-LCD device.
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中文摘要--------------------------------------------------------------------------------i
英文摘要--------------------------------------------------------------------------------- ii
謝誌----------------------------------------------------------------------------------------i v
目錄-----------------------------------------------------------------------------------------v
Scheme目錄---------------------------------------------------------------------------- viii
Table 目錄--------------------------------------------------------------------------------xi
Figure 目錄--------------------------------------------------------------------------------x
第一章 緒論--------------------------------------------------------------------------1
1-1 簡介---------------------------------------------------------------------------1
1-2 液晶配向簡介----------------------------------------------------------------2
1-3 配向膜之要求---------------------------------------------------------------4
1-4 預傾角------------------------------------------------------------------------4
1-5 定向摩擦之缺點---------------------------------------------------------------5
1-6 光配向技術------------------------------------------------------------------6
1-7 光配向材料------------------------------------------------------------------6
1-8 研究動機----------------------------------------------------------------------10
第二章 實驗部份-----------------------------------------------------------------------11
2-1試藥-----------------------------------------------------------------------------11
2-2測試儀器-----------------------------------------------------------------------11
2-3合成-----------------------------------------------------------------------------12
2-4液晶盒製作方法--------------------------------------------------------------17
2-4-1 薄膜製備-----------------------------------------------------------------17
2-4-2 液晶盒的製備-----------------------------------------------------------19
2-4-3 液晶盒中液晶配向之評估方法--------------------------------------20
2-5 電壓與光穿透率之量測----------------------------------------------------20
2-6 預傾角之量測----------------------------------------------------------------21
2-7 扭轉錨定能量之量測-------------------------------------------------------22
第三章 結果與討論--------------------------------------------------------------------25
3-1 碟狀分子之紅外光譜分析-------------------------------------------------25
3-2光配向膜之聚合機制--------------------------------------------------------27
3-2-1 聚合反應-----------------------------------------------------------------27
3-2-2 薄膜分析-----------------------------------------------------------------29
3-2-3 紫外可見光譜分析-----------------------------------------------------32
3-3 液晶盒的製作----------------------------------------------------------------33
3-4 配向膜排列方向之分析----------------------------------------------------41
3-4-1排列效果之分析--------------------------------------------------------35
3-4-2誘導液晶排列方向之測量--------------------------------------------39
3-4 熱穩定性的量測-------------------------------------------------------------45
3-5 光穩定性的量測-------------------------------------------------------------47
3-6 電壓-穿透率的量測---------------------------------------------------------49
3-7 預傾角的量測----------------------------------------------------------------50
3-8扭轉錨定能量-----------------------------------------------------------------52
第四章 結論-----------------------------------------------------------------------------56
第五章 參考文獻-----------------------------------------------------------------------57
List of Schemes
Scheme 1 Synthesis of monomer HTP6Ac---------------------------------------15
Scheme 2 Synthesis of monomer HTP6Ci----------------------------------------16
Scheme 3 NMR of monomer HTP6Ac--------------------------------------------60
Scheme 4 NMR of monomer HTP6Ci--------------------------------------------61
List of tables
Table 3-1 IR dichroism of the HTP6Ac film-------------------------------------43
Table 3-2 LC alignment characteristics in cell constructed using LPUV irradiated four discotic thin films ------------------------------------44
Table 3-3 Calculated results for the anchoring energy.(A) HTP6Ac、HTP6Ci (B) HTP11Ep、HTP11Cu ---------------------------------------------53
List of Figures
Figure 1-1 Fundamental molecular alignments of LC on the alignment layers ------------------------------------------------------------------------------2
Figure 1-2 The texture of reverse-twist domains on a LCD panel--------------3
Figure 1-3 LC pretilt angle on a substrate-----------------------------------------5
Figure 1-4 The formation of disclination line on TN-LCD devices------------6
Figure 1-5 Azobenene-containing photo-alignment material--------------------7
Figure 1-6 PI for photo-alignment application------------------------------------6
Figure 1-7 Photodimerization materials for photo-alignment application-----8
Figure 1-8 The photo-dimerization reaction of PVCi molecules---------------8
Figure 1-9 Polarized light induced changes of poly(vinylcinnamate) film surface---------------------------------------------------------------------9
Figure 1-10 Polarized light induced changes of coumarin-based polymer-----9
Figure 1-11 The molecular structure of decided discotic materials-------------10
Figure 2-1 The way to irradiate LPUV on discotic film------------------------18
Figure 2-2 Brewster’s angle,the refracted and reflected rays of an incident beam are perpendicular------------------------------------------------18
Figure 2-3 Experimental setup for the V-T curve measurement---------------20
Figure 2-4 Experimental setup for the Phase retardation extrema method used to measure the pretilt angle -------------------------------------------26
Figure 2-5 LC cell prepared for double cells to measure twist anchoring energy--------------------------------------------------------------------23
Figure 2-6 Schematic drawing of twist anchoring energy measure -----------24
Figure 3-1 FT-IR spectrum of HTP6Ac ------------------------------------------25
Figure 3-2 FT-IR spectrum of HTP6Ci -------------------------------------------26
Figure 3-3 Crosslinked structures of different discotic photo-alignment materials(a)HTP6Ac (b)HTP6Ci (c)HTP11Ep(d)HTP11Cu -----31
Figure 3-4 UV conventional spectra of a HTP6Ac film irradiated UV light from 0 J to 830 J--------------------------------------------------------32
Figure 3-5 UV conventional spectra of a HTP6Ci film irradiated UV light from 0 J to 15 J.---------------------------------------------------------33
Figure 3-6 Pictures of Newton circles---------------------------------------------34
Figure 3-7 The interferogram of an empty LC cell.-----------------------------34
Figure 3-8 The POM pictures of MLC-2042 LC cells alignmed by HTP6Ac discotic film irradiated with different exposured energy by LPUV.--------------------------------------------------------------------36
Figure 3-9 The POM pictures of MLC-2042 LC cells alignmed by HTP6Ci discotic film irradiated with different exposured energy by LPUV ----------------------------------------------------------------------------37
Figure 3-10 Experimental setup for measuring the UV-induced LC alignment----------------------------------------------------------------38
Figure 3-11 Polarized UV-visible spectrum of a dye dopeing MLC-2042 aligned by HTP6Ac film-----------------------------------------------38
Figure 3-12 Order parameter for LC cells contain different alignment layer ----------------------------------------------------------------------------39
Figure 3-13 Polar diagrams of the dye-doped homogeneous LPUV irradiated MLC-2042 cells contain different alignment layer (a) HTP6Ac (b) HTP6Ci (c) HTP11Ep (d) HTP11Cu---------------------------------41
Figure 3-14 Experimental setup for the measurement of polarized FT-IR spectrum-----------------------------------------------------------------42
Figure 3-15 Above: IR dichroic difference spectrium of a 108 J irradiated HTP6Ac film. Below:Conventional IR absorbance spectra of a HTP6Ac film before and after irradiation---------------------------43
Figure 3-16 Thermal stability of dye-doped LC cell of different time at constant temperature 70℃---------------------------------------------46
Figure 3- 17 Thermal stability of dye-doped LC cell of different time at constant temperature 120℃-------------------------------------------46
Figure 3-18 Photostability of dye-doped LC cell of different exposure energy ----------------------------------------------------------------------------48
Figure 3-19 V-T curve of a homogeneous cell prepared with LPUV- irradiated HTP6Ac film------------------------------------------------------------49
Figure 3-20 V-T curve of a homogeneous cell prepared with LPUV- irradiated HTP6Ci film-------------------------------------------------------------50
Figure 3-21 The pretilt angle of various thin films generated at different oblique angle. LC mixing is MLC-2042-----------------------------51
Figure 3-22 Twist anchoring energy for various photoalignment thin films generated at different oblique angles. LC mixture is MLC-2042 with chiral----------------------------------------------------------------55
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