TW201523130A - 硬化膜形成組成物、配向材及相位差材 - Google Patents
硬化膜形成組成物、配向材及相位差材 Download PDFInfo
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- TW201523130A TW201523130A TW103129540A TW103129540A TW201523130A TW 201523130 A TW201523130 A TW 201523130A TW 103129540 A TW103129540 A TW 103129540A TW 103129540 A TW103129540 A TW 103129540A TW 201523130 A TW201523130 A TW 201523130A
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- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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- 238000001226 reprecipitation Methods 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- JQZAKMJZYGPUFD-UHFFFAOYSA-N spiro[3.3]heptane-2,6-dicarboxylic acid Chemical compound C1C(C(=O)O)CC21CC(C(O)=O)C2 JQZAKMJZYGPUFD-UHFFFAOYSA-N 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- DFKSOSAMNIMACB-UHFFFAOYSA-N sulfanyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OS DFKSOSAMNIMACB-UHFFFAOYSA-N 0.000 description 1
- AZADLAPXFZPRFJ-UHFFFAOYSA-N sulfanylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCS AZADLAPXFZPRFJ-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
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- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- AGKLVMVJXDFIGC-MDZDMXLPSA-N tert-butyl (e)-3-phenylprop-2-enoate Chemical compound CC(C)(C)OC(=O)\C=C\C1=CC=CC=C1 AGKLVMVJXDFIGC-MDZDMXLPSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- QWFRRFLKWRIKSZ-UHFFFAOYSA-N truxillic acid Chemical compound OC(=O)C1C(C=2C=CC=CC=2)C(C(O)=O)C1C1=CC=CC=C1 QWFRRFLKWRIKSZ-UHFFFAOYSA-N 0.000 description 1
- 235000013976 turmeric Nutrition 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical compound C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
- C08G69/50—Polymers modified by chemical after-treatment with aldehydes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
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Abstract
提供形成具備優異的光反應效率與耐溶劑性
之硬化膜的硬化膜形成組成物且提供光配向用之配向材及使用該配向材而形成的相位差材。
硬化膜形成組成物含有(A)具有光配向性
基與羥基、羧基及胺基中選出之任1個取代基之化合物、(B)醯胺基的氮原子之中至少一部份經烷氧基甲基化或烷基硫甲基化的聚醯胺及(C)交聯觸媒。使用該硬化膜形成組成物形成硬化膜,利用光配向技術形成配向材。配向材上塗佈聚合性液晶,使硬化而得到相位差材。
Description
本發明係關於硬化膜形成組成物、配向材及相位差材。
近年來,使用液晶面板之電視等之顯示器領域中,已進展可享受3D影像之3D顯示器之開發作為朝向高性能化之取向。3D顯示器係藉由例如以觀察者之右眼辨識右眼用影像,以觀察者之左眼辨識左眼用影像,而可顯示立體感之影像。
顯示3D影像之3D顯示器之方式有多樣者,作為不須專用眼鏡之方式,已知有柱狀透鏡(lenticular lens)方式及視差屏障(parallax barrier)方式等。
而且,作為觀察者配戴眼鏡觀察3D影像之顯示器之方式之一已知有圓偏光眼鏡方式等(參照例如專利文獻1)。
圓偏光眼鏡方式之3D顯示器之情況,通常在
液晶面板等之形成影像之顯示元件上配置經圖型化之相位差材。該經圖型化之相位差材係分別複數、規則地配置相位差特性不同之2種相位差區域而構成。又,以下,本說明書中,將配置此種相位差特性不同之複數個相位差區域之方式而圖型化之相位差材稱為圖型化相位差材。
圖型化相位差材係如專利文獻2所揭示,可藉由使由聚合性液晶所成之相位差材料進行光學圖型化而製作。由聚合性液晶所成之相位差材料之光學圖型化係利用於液晶面板之配向材形成中已知之光配向技術。亦即,於基板上設置由光配向性之材料所成之塗膜,對其照射偏光方向不同之2種偏光。接著,獲得形成有液晶之配向控制方向不同之2種液晶配向區域之作為配向材之光配向膜。於該光配向膜上塗佈包含聚合性液晶之溶液狀之相位差材料,而實現聚合性液晶之配向。隨後,使經配向之聚合性液晶硬化,形成圖型化相位差材。
使用液晶面板之光配向技術之配向材形成中,作為可利用之光配向性之材料,已知有側鏈具有桂皮醯基(cinnamoyl)及查爾酮(chalconc)基等之光二聚化部位之丙烯酸樹脂或聚醯亞胺樹脂等。已報導該等樹脂藉由偏光UV照射,而顯示控制液晶配向之性能(以下亦稱為液晶配向性)(參照專利文獻3至專利文獻5)。
[專利文獻1]日本特開平10-232365號公報
[專利文獻2]日本特開2005-49865號公報
[專利文獻3]日本專利第3611342號公報
[專利文獻4]日本特開2009-058584號公報
[專利文獻5]日本特表2001-517719號公報
但是,根據本發明者們之檢討,可知如此於側鏈具有桂皮醯基或查耳酮基等的光二聚化部位之丙烯酸樹脂,用作為相位差材的形成的場合無法得到充分特性(配向感度)。尤其、對此等之樹脂照射偏光UV,形成配向材,使用該配向材,進行由聚合性液晶所構成之相位差材料之光學圖案化,需要大的偏光UV曝光量。該偏光UV曝光量比使一般的液晶面板用的液晶配向之足夠偏光UV曝光量(例如100mJ/cm2左右。)多很多。
偏光UV曝光量變多的理由方面,可舉例如於相位差材形成的場合,與液晶面板用的液晶相異,聚合性液晶以溶液之狀態使用而塗佈於配向材上。
具體上使用側鏈具有桂皮醯基等的光二聚化部位的丙烯酸樹脂等,形成配向材,並使用該配向材使聚合性液晶配向之場合,首先在丙烯酸樹脂等中進行光二聚化反應所致之光交聯。而,至對聚合性液晶溶液表現耐性為止,需要進行大曝光量的偏光照射。
另一方面,為使液晶面板的液晶進行配向,通常僅使光配向性之配向材的表面進行二聚化反應即可。
但,使用上述丙烯酸樹脂等的以往材料,欲於配向材表現對聚合性液晶溶液之耐性(溶劑耐性),則反應需進行至配向材的內部,變得需要更多的曝光量。結果,有以往材料之配向感度變得非常小之問題。
又,為了於上述以往材料之樹脂表現如此之溶劑耐性,已知添加交聯劑之技術。但,得知進行交聯劑所致之熱硬化反應後,於形成的塗膜之內部形成3次元構造,光反應性降低。亦即即使於以往材料中添加交聯劑使用,結果配向感度大幅降低,無法得到所期望之效果。
由以上,追求使配向材的配向感度提升且可降低偏光UV曝光量之光配向技術、與該配向材的形成使用的硬化膜形成組成物。且追求可高效率提供圖型化相位差材之技術。
又,使用光配向技術,製造3D顯示器之圖型化相位差材之場合,以往係在玻璃基板上形成。但,近年因應製造花費降低之要求,追求於TAC(三乙醯纖維素)薄膜、COP(環烯烴聚合物)薄膜等之便宜的樹脂薄膜上以所謂連續捲軸式生產。
但是,在上述般以往材料所形成的光配向膜,對樹脂薄膜之密著性弱、在樹脂薄膜上製造高信賴之圖型化相位差材有困難。
因此,追求對樹脂薄膜之密著性優異、即使
在TAC薄膜等的樹脂薄膜上可形成高信賴的相位差材,可適用於光配向技術的配向材與形成該配向材用之硬化膜形成組成物。
本發明為基於以上的知識或檢討結果而成者。亦即,本發明的目的為提供具有優異的光反應效率且具備耐溶劑性,即使在樹脂薄膜上可以高感度使聚合性液晶配向之配向材用之硬化膜形成組成物。
而,本發明的別的目的為提供由該硬化膜形成組成物所得到,具有優異的光反應效率且具備耐溶劑性,即使在樹脂薄膜上可以高感度使聚合性液晶配向之配向材與使用該配向材形成的相位差材。
本發明的其他目的及優點由以下的記載可明白。
本發明的第1態樣為一種硬化膜形成組成物,其特徵係含有(A)具有光配向性基、與由羥基、羧基、胺基及烷氧基矽烷基中選出之任1個取代基之化合物、(B)醯胺基的氮原子之中至少一部份經烷氧基甲基化或烷基硫甲基化的聚醯胺、及(C)交聯觸媒。
本發明的第1態樣中,
(A)成分的光配向性基以進行光二聚化或光異構化之
構造之官能基為佳。
本發明的第1態樣中,
(A)成分的光配向性基以桂皮醯基為佳。
本發明的第1態樣中,
(A)成分的光配向性基以偶氮苯構造之基為佳。
本發明的第1態樣中,
(B)成分的聚醯胺以使尼龍-6、尼龍-11、尼龍-12、尼龍-66、尼龍-610、尼龍-612、尼龍-1010、尼龍-1212、尼龍-66/610、尼龍6/66、尼龍6/69、尼龍6-I/6-T、及此等之2種以上的組合所構成之群中選出的聚醯胺進行N-烷氧基甲基化或N-烷基硫甲基化者為佳。
本發明的第1態樣中,(B)成分的聚醯胺以使聚醯胺進行N-烷氧基甲基化者為佳。
本發明的第1態樣中,除(A)成分、(B)成分及(C)成分外,以進一步含有(D)具有碳原子數2~5之羥基烷基酯基、烷氧基矽烷基、N-烷氧基甲基、羧基及酚性羥基之中至少一個的丙烯酸聚合物為佳。
本發明的第1態樣中,(B)成分的聚醯胺以具有1,000~100,000的重量平均分子量為佳。
本發明的第2之態樣係關於使用本發明的第1態樣之熱硬化膜形成組成物而得到的配向材。
本發明的第3之態樣係關於使用本發明的第1態樣之硬化膜形成組成物所得到的硬化膜而形成的相位差材。
根據本發明的第1態樣,可提供用以提供具備優異的光反應效率與耐溶劑性,可以高感度使聚合性液晶配向、顯示與基板之高密著性的配向材之硬化膜形成組成物。
根據本發明的第2之態樣,可提供具備優異的光反應效率與耐溶劑性,可以高感度使聚合性液晶配向、顯示與基板之高密著性的配向材。
根據本發明的第3之態樣,可提供即使在樹脂薄膜上,可以高效率形成、且可光學圖案化之相位差材。
本實施形態之硬化膜形成組成物含有(A)成分之低分子的光配向成分、與(B)成分之醯胺基的氮原子之中至少一部份經烷氧基甲基化或烷基硫甲基化的聚醯胺及(C)成分之交聯觸媒。本實施形態之硬化膜形成組成物除(A)成分、(B)成分及(C)成分,進一步可含有作為(D)成分之具有碳原子數2~5之羥基烷基酯基、烷氧基矽烷基、N-烷氧基甲基、羧基及酚性羥基之中至少一個的丙烯酸聚合物。而,在不損及本發明的效果範圍,可含有其他添加劑。
以下,詳細說明各成分。
本發明的組成物的(A)成分為低分子配向成分。(A)成分為對由本發明的組成物所得到的本實施形態之硬化膜賦予光配向性之成分,與成為基質之後述(B)成分的聚合物相比為低分子的光配向成分。
本發明的組成物中,(A)成分之低分子配向成分具有光配向性基、以及羥基、羧基、胺基及烷氧基矽烷基所組成群中選出的一個基之化合物。
又,本發明中,光配向性基係指具有進行光二聚化的構造之官能基或具有進行光異構化的構造之官能基。又光配向性基方面,亦可使用引發photo Fries rearrangement反應之官能基(例示化合物:安息香酸酯化合物等)、引發光分解反應之基(例示化合物;環丁烷環等)等。
又,(A)成分的化合物可具有作為光配向性基之進行光二聚化之構造部位係指藉由光照射形成二聚物的部位,其具體例方面,可舉例如桂皮醯基、查耳酮基、香豆素基、蒽基等。此等中,由在可見光領域透明性高、以及高光二聚化反應性,以桂皮醯基為佳。
又,(A)成分的化合物可具有作為光配向性基之進行光異構化之構造部位係指,藉由光照射變換成順式體與反式體之構造部位,其具體例,可舉例如偶氮苯構造、茋構造等所構成的部位。此等中,由高反應性以偶氮苯構造為佳。
具有光配向性基、與羥基、羧基、胺基及烷氧基矽烷基所組成群中選出的一個的化合物的具體例,如下述式[A1]~式[A5]所示。又A成分的化合物不被下述具體例限定。
前述式中、A1與A2各自獨立,表示氫原子或甲基。
X1為單鍵、醚鍵、酯鍵、羰基、醯胺鍵、胺基甲酸乙酯鍵、脲鍵、胺基鍵及彼等之組合中選出的1種或2種以上的鍵、或者間隔該1種或2種之鍵,鍵結碳原子數1~18之伸烷基、伸苯基、伸聯苯基及彼等之組合中選出的1~3之取代基而成之構造,且前述取代基可為間隔前述
鍵,各自複數個連結而成之構造。
X2為氫原子、鹵素原子、氰基、碳原子數1~18之烷基、苯基、聯苯基或環己基。此時,碳原子數1~18之烷基、苯基、聯苯基及環己基可透過共價鍵、醚鍵、酯鍵、醯胺鍵或尿素鍵鍵結。
X3為羥基、巰基、碳原子數1~10的烷氧基、碳原子數1~10的烷基硫基、苯基、苯氧基、聯苯基、聯苯基氧基。
X4各自獨立,為單鍵、碳原子數1~20的伸烷基、芳香族環基、或、脂肪族環基。在此碳原子數1~20的伸烷基可為分支狀或直鏈狀。
X5為羥基、羧基、胺基或烷氧基矽烷基。
X為單鍵、氧原子或硫原子。
又,此等之取代基中,苯基與聯苯基可被碳原子數1~4的烷基、碳原子數1~4的烷氧基、鹵素原子、三氟甲基及氰基中選出的相同或不同的1個或複數之取代基所取代。
上述式中、R1、R2、R3、R4、R5、R6、R7及R8各自獨立,為氫原子、碳原子數1~4的烷基、碳原子數1~4的烷氧基、鹵素原子、三氟甲基或氰基。
(A)成分之具有光配向性基及羥基的化合物的具體例,作為上述式[A1]~[A5]所表示之化合物以及該式以外之化合物,例如4-(8-羥基辛基氧基)桂皮酸甲基酯、4-(6-羥基己基氧基)桂皮酸甲基酯、4-(4-羥基丁基氧基)桂
皮酸甲基酯、4-(3-羥基丙基氧基)桂皮酸甲基酯、4-(2-羥基乙基氧基)桂皮酸甲基酯、4-羥基甲基氧基桂皮酸甲基酯、4-羥基桂皮酸甲基酯、4-(8-羥基辛基氧基)桂皮酸乙基酯、4-(6-羥基己基氧基)桂皮酸乙基酯、4-(4-羥基丁基氧基)桂皮酸乙基酯、4-(3-羥基丙基氧基)桂皮酸乙基酯、4-(2-羥基乙基氧基)桂皮酸乙基酯、4-羥基甲基氧基桂皮酸乙基酯、4-羥基桂皮酸乙基酯、4-(8-羥基辛基氧基)桂皮酸苯基酯、4-(6-羥基己基氧基)桂皮酸苯基酯、4-(4-羥基丁基氧基)桂皮酸苯基酯、4-(3-羥基丙基氧基)桂皮酸苯基酯、4-(2-羥基乙基氧基)桂皮酸苯基酯、4-羥基甲基氧基桂皮酸苯基酯、4-羥基桂皮酸苯基酯、4-(8-羥基辛基氧基)桂皮酸聯苯基酯、4-(6-羥基己基氧基)桂皮酸聯苯基酯、4-(4-羥基丁基氧基)桂皮酸聯苯基酯、4-(3-羥基丙基氧基)桂皮酸聯苯基酯、4-(2-羥基乙基氧基)桂皮酸聯苯基酯、4-羥基甲基氧基桂皮酸聯苯基酯、4-羥基桂皮酸聯苯基酯、桂皮酸8-羥基辛基酯、桂皮酸6-羥基己基酯、桂皮酸4-羥基丁基酯、桂皮酸3-羥基丙基酯、桂皮酸2-羥基乙基酯、桂皮酸羥基甲基酯、4-(8-羥基辛基氧基)偶氮苯、4-(6-羥基己基氧基)偶氮苯、4-(4-羥基丁基氧基)偶氮苯、4-(3-羥基丙基氧基)偶氮苯、4-(2-羥基乙基氧基)偶氮苯、4-羥基甲基氧基偶氮苯、4-羥基偶氮苯、4-(8-羥基辛基氧基)查耳酮、4-(6-羥基己基氧基)查耳酮、4-(4-羥基丁基氧基)查耳酮、4-(3-羥基丙基氧基)查耳酮、4-(2-羥基乙基氧基)查耳酮、4-羥基甲基氧基查耳酮、4-羥基查耳酮、
4’-(8-羥基辛基氧基)查耳酮、4’-(6-羥基己基氧基)查耳酮、4’-(4-羥基丁基氧基)查耳酮、4’-(3-羥基丙基氧基)查耳酮、4’-(2-羥基乙基氧基)查耳酮、4’-羥基甲基氧基查耳酮、4’-羥基查耳酮、7-(8-羥基辛基氧基)香豆素、7-(6-羥基己基氧基)香豆素、7-(4-羥基丁基氧基)香豆素、7-(3-羥基丙基氧基)香豆素、7-(2-羥基乙基氧基)香豆素、7-羥基甲基氧基香豆素、7-羥基香豆素、6-羥基辛基氧基香豆素、6-羥基己基氧基香豆素、6-(4-羥基丁基氧基)香豆素、6-(3-羥基丙基氧基)香豆素、6-(2-羥基乙基氧基)香豆素、6-羥基甲基氧基香豆素、6-羥基香豆素。
(A)成分之具有光配向性基及羧基的化合物的具體例方面,可舉例如桂皮酸、阿魏酸、4-硝基桂皮酸、4-甲氧基桂皮酸、3,4-二甲氧基桂皮酸、香豆素-3-羧酸、4-(N,N-二甲基胺基)桂皮酸等。
(A)成分之具有光配向性基及胺基的化合物的具體例方面,可舉例如4-胺基桂皮酸甲基酯、4-胺基桂皮酸乙基酯、3-胺基桂皮酸甲基酯、3-胺基桂皮酸乙基酯等。
(A)成分之具有光配向性基與烷氧基矽烷基之化合物的具體例方面,可舉例如4-(3-三甲氧基矽烷基丙基氧基)桂皮酸甲基酯、4-(3-三乙氧基矽烷基丙基氧基)桂皮酸甲基酯、4-(3-三甲氧基矽烷基丙基氧基)桂皮酸乙基酯、4-(3-三乙氧基矽烷基丙基氧基)桂皮酸乙基酯、4-(6-三甲氧基矽烷基己基氧基)桂皮酸甲基酯、4-(6-三乙氧基
矽烷基己基氧基)桂皮酸甲基酯、4-(6-三甲氧基矽烷基己基氧基)桂皮酸乙基酯及4-(6-三乙氧基矽烷基己基氧基)桂皮酸乙基酯等。
(A)成分之低分子配向成分,可舉例如以上的具體例,但不限於此等。
又,(A)成分之低分子配向成分為具有光配向性基及羥基的化合物之場合,作為(A)成分,可使用分子內具有光配向性基2個以上及/或羥基2個以上之化合物。具體上作為(A)成分,可使用分子內具有1個羥基與2個以上的光配向性基之化合物、或分子內具有1個光配向性基與2個以上的羥基之化合物、或分子內具有光配向性基與羥基各2個以上之化合物。例如分子內具有光配向性基與羥基各2個以上之化合物,可舉例如下述式所表示之化合物。
藉由適宜選擇如此化合物,可使(A)成分之低分子配向成分之分子量控制於所期望範圍之值。為了使用本發明的組成物,形成本實施形態之硬化膜,雖需要加熱硬化,但可抑制進行該加熱時,(A)成分之低分子配向成
分昇華。
又,本發明的組成物中(A)成分的化合物方面,可為具有光配向性基與羥基、羧基、胺基及烷氧基矽烷基任一個之複數種化合物的混合物。
又本發明的組成物,作為(A)成分,可含有具有下述式[1]所表示之光配向性基之化合物。
式中、A1與A2各自獨立,為氫原子或甲基,A3為羥基、巰基、碳原子數1~10的烷氧基、碳原子數1~10的羥基烷氧基、碳原子數1~10的烷基硫基、苯基、苯氧基、聯苯基或聯苯基氧基,*為鍵結端。
在此上述苯環與苯基的氫原子,各自獨立可被碳原子數1~10的烷基、碳原子數1~10的烷氧基、鹵素原子、氰基及硝基中選出的取代基所取代。
其中,上述A1方面,以氫原子或甲基為佳、A2以氫原子為佳、A3以碳原子數1~10的烷氧基、苯基等為佳。
上述式[1]所表示之具有光配向性基及羥基的化合物的具體例方面,例如4-[4-(8-羥基辛基氧基)苯甲醯
基]桂皮酸甲基酯、4-[4-(6-羥基己基氧基)苯甲醯基]桂皮酸甲基酯、4-[4-(4-羥基丁基氧基)苯甲醯基]桂皮酸甲基酯、4-[4-(3-羥基丙基氧基)苯甲醯基]桂皮酸甲基酯、4-[4-(2-羥基乙基氧基)苯甲醯基]桂皮酸甲基酯、4-[4-羥基甲基氧基苯甲醯基]桂皮酸甲基酯、4-[4-羥基苯甲醯基]桂皮酸甲基酯、4-[4-(8-羥基辛基氧基)苯甲醯基]桂皮酸乙基酯、4-[4-(6-羥基己基氧基)苯甲醯基]桂皮酸乙基酯、4-[4-(4-羥基丁基氧基)苯甲醯基]桂皮酸乙基酯、4-[4-(3-羥基丙基氧基)苯甲醯基]桂皮酸乙基酯、4-[4-(2-羥基乙基氧基)苯甲醯基]桂皮酸乙基酯、4-[4-羥基甲基氧基苯甲醯基]桂皮酸乙基酯、4-[4-羥基苯甲醯基]桂皮酸乙基酯、4-[4-(8-羥基辛基氧基)苯甲醯基]桂皮酸第三丁基酯、4-[4-(6-羥基己基氧基)苯甲醯基]桂皮酸第三丁基酯、4-[4-(4-羥基丁基氧基)苯甲醯基]桂皮酸第三丁基酯、4-[4-(3-羥基丙基氧基)苯甲醯基]桂皮酸第三丁基酯、4-[4-(2-羥基乙基氧基)苯甲醯基]桂皮酸第三丁基酯、4-[4-羥基甲基氧基苯甲醯基]桂皮酸第三丁基酯、4-[4-(8-羥基辛基氧基)苯甲醯基]桂皮酸苯基酯、4-[4-(6-羥基己基氧基)苯甲醯基]桂皮酸苯基酯、4-[4-(4-羥基丁基氧基)苯甲醯基]桂皮酸苯基酯、4-[4-(3-羥基丙基氧基)苯甲醯基]桂皮酸苯基酯、4-[4-(2-羥基乙基氧基)苯甲醯基]桂皮酸苯基酯、4-[4-羥基甲基氧基苯甲醯基]桂皮酸苯基酯、4-[4-羥基苯甲醯基]桂皮酸苯基酯、4-[4-(8-羥基辛基氧基)苯甲醯基]桂皮酸聯苯基酯、4-[4-(6-羥基己基氧基)苯甲醯基]桂皮酸聯苯基酯、4-[4-(4-羥基丁
基氧基)苯甲醯基]桂皮酸聯苯基酯、4-[4-(3-羥基丙基氧基)苯甲醯基]桂皮酸聯苯基酯、4-[4-(2-羥基乙基氧基)苯甲醯基]桂皮酸聯苯基酯、4-[4-羥基甲基氧基苯甲醯基]桂皮酸聯苯基酯、4-[4-羥基苯甲醯基]桂皮酸聯苯基酯、4-苯甲醯基桂皮酸8-羥基辛基酯、4-苯甲醯基桂皮酸6-羥基己基酯、4-苯甲醯基桂皮酸4-羥基丁基酯、4-苯甲醯基桂皮酸3-羥基丙基酯、4-苯甲醯基桂皮酸2-羥基乙基酯、4-苯甲醯基桂皮酸羥基甲基酯、4-[4-(8-羥基辛基氧基)苯甲醯基]查耳酮、4-[4-(6-羥基己基氧基)苯甲醯基]查耳酮、4-[4-(4-羥基丁基氧基)苯甲醯基]查耳酮、4-[4-(3-羥基丙基氧基)苯甲醯基]查耳酮、4-[4-(2-羥基乙基氧基)苯甲醯基]查耳酮、4-(4-羥基甲基氧基苯甲醯基)查耳酮、4-(4-羥基苯甲醯基)查耳酮等。
上述式[1]所表示之具有光配向性基及羧基的化合物的具體例方面,可舉例如4-苯甲醯基桂皮酸、4-(4-硝基苯甲醯基)桂皮酸、4-(4-甲氧基苯甲醯基)桂皮酸、4-(3,4-二甲氧基苯甲醯基)桂皮酸等。
上述式[1]所表示之具有光配向性基及胺基的化合物的具體例方面,可舉例如4-(4-胺基苯甲醯基)桂皮酸甲基酯、4-(4-胺基苯甲醯基)桂皮酸乙基酯、4-(4-胺基苯甲醯基)桂皮酸第三丁基酯、4-(3-胺基苯甲醯基)桂皮酸甲基酯、4-(3-胺基苯甲醯基)桂皮酸乙基酯、4-(3-胺基苯甲醯基)桂皮酸第三丁基酯等。
上述式[1]所表示之具有光配向性基與烷氧基
矽烷基之化合物的具體例方面,可舉例如4-[4-(3-三甲氧基矽烷基丙基氧基)苯甲醯基]桂皮酸甲基酯、4-[4-(3-三乙氧基矽烷基丙基氧基)苯甲醯基]桂皮酸甲基酯、4-[4-(3-三甲氧基矽烷基丙基氧基)苯甲醯基]桂皮酸乙基酯、4-[4-(3-三乙氧基矽烷基丙基氧基)苯甲醯基]桂皮酸乙基酯、4-[4-(3-三甲氧基矽烷基丙基氧基)苯甲醯基]桂皮酸第三丁基酯、4-[4-(3-三乙氧基矽烷基丙基氧基)苯甲醯基]桂皮酸第三丁基酯、4-[4-(6-三甲氧基矽烷基己基氧基)苯甲醯基]桂皮酸甲基酯、4-[4-(6-三乙氧基矽烷基己基氧基)苯甲醯基]桂皮酸甲基酯、4-[4-(6-三甲氧基矽烷基己基氧基)苯甲醯基]桂皮酸乙基酯、4-[4-(6-三乙氧基矽烷基己基氧基)苯甲醯基]桂皮酸乙基酯、4-[4-(6-三甲氧基矽烷基己基氧基)苯甲醯基]桂皮酸第三丁基酯及4-[4-(6-三乙氧基矽烷基己基氧基)苯甲醯基]桂皮酸第三丁基酯等。
又,具有上述式[1]所表示之基作為光配向性基的化合物方面,例如下述式[2]所表示之化合物。
上述式[2]中、A1與A2各自獨立,為氫原子或甲基,A3為羥基、巰基、碳原子數1~10的烷氧基、碳原子數1~10的羥基烷氧基、碳原子數1~10的烷基硫基、
苯基、苯氧基、聯苯基或聯苯基氧基,在此苯環與苯基的氫原子,各自獨立可被碳原子數1~10的烷基、碳原子數1~10的烷氧基、鹵素原子、氰基及硝基中選出的取代基所取代,n為2~20的整數。
該化合物為文獻未記載的新穎化合物,可以例如下述路徑所示之方法製造。
上述式中、A1、A2、A3及n同前述式[2]所定義者,Hal為鹵素原子。
本實施形態之硬化膜形成組成物,含有醯胺基的氮原子之中至少一部份經烷氧基甲基化或烷基硫甲基化的聚醯胺作為(B)成分。
本發明中之(B)成分的聚醯胺,可使用經ω-胺基羧酸
之聚縮合、該內醯胺之開環聚合而合成的聚醯胺、或經二羧酸與二胺之聚縮合等而合成的聚醯胺、或者此等之2種以上的共聚合或者摻混物。
經ω-胺基羧酸之聚縮合、或其內醯胺之開環聚合而合成的聚醯胺,例如Nylon Plastics(Melvin L.Kohan編,1973,John Wiley and Sons,Inc.)所揭示,作為如此者,可舉例如尼龍-6、尼龍-11、尼龍-12、或此等之2種以上的組合。由超過1種類之上述內醯胺或上述胺基羧酸所調製的聚醯胺方面,可舉例如尼龍-6,12。使用頻率高的聚醯胺方面,可舉例如尼龍-6、尼龍-11、尼龍-12、及尼龍-6,12、或此等之2種以上的組合。
以二羧酸與二胺之聚縮合等製造聚醯胺時之二胺成分方面,以脂肪族二胺或脂環式二胺等的不具有芳香族環之二胺為佳。
脂肪族二胺類之例方面,可舉例如1,2-二胺基乙烷、1,3-二胺基丙烷、1,4-二胺基丁烷、1,5-二胺基戊烷、1,6-二胺基己烷、1,7-二胺基庚烷、1,8-二胺基辛烷、1,9-二胺基壬烷、1,10-二胺基癸烷、1,3-二胺基-2,2-二甲基丙烷、1,6-二胺基-2,5-二甲基己烷、1,7-二胺基-2,5-二甲基庚烷、1,7-二胺基-4,4-二甲基庚烷、1,7-二胺基-3-甲基庚烷、1,9-二胺基-5-甲基庚烷、1,12-二胺基十二烷、1,18-二胺基十八烷、1,2-雙(3-胺基丙氧基)乙烷等。
脂環式二胺之例方面,可舉例如1,4-二胺基環己烷、1,3-二胺基環己烷、4,4’-二胺基二環己基甲烷、
4,4’-二胺基-3,3’-二甲基二環己基胺、異佛爾酮二胺等。
又,製造本發明使用的聚醯胺時,在不損及本發明的效果範圍,可使用芳香族二胺、芳香族-脂肪族二胺、雜環式二胺等。此時,此等芳香族二胺、芳香族-脂肪族二胺、雜環式二胺等的合計量,全二胺之合計量每100莫耳以10莫耳以下為佳。芳香族二胺、芳香族-脂肪族二胺、雜環式二胺等的含量過大,則N-烷氧基甲基改性時甲醛與芳香族環進行反應,有得到的樹脂的操作性、物性等降低之情形。
芳香族二胺類之例方面,可舉例如o-伸苯基二胺、m-伸苯基二胺、p-伸苯基二胺、2,4-二胺基甲苯、2,5-二胺基甲苯、3,5-二胺基甲苯、1,4-二胺基-2-甲氧基苯、2,5-二胺基-p-二甲苯、1,3-二胺基-4-氯苯、3,5-二胺基安息香酸、1,4-二胺基-2,5-二氯苯、4,4’-二胺基-1,2-二苯基乙烷、4,4’-二胺基-2,2’-二甲基聯苄基、4,4’-二胺基二苯基甲烷、3,3’-二胺基二苯基甲烷、3,4’-二胺基二苯基甲烷、4,4’-二胺基-3,3’-二甲基二苯基甲烷、2,2’-二胺基茋、4,4’-二胺基茋、4,4’-二胺基二苯基醚、3,4’-二胺基二苯基醚、4,4’-二胺基二苯基硫化物、4,4’-二胺基二苯基碸、3,3’-二胺基二苯基碸、4,4’-二胺基二苯甲酮、1,3-雙(3-胺基苯氧基)苯、1,3-雙(4-胺基苯氧基)苯、1,4-雙(4-胺基苯氧基)苯、3,5-雙(4-胺基苯氧基)安息香酸、4,4’-雙(4-胺基苯氧基)聯苄基、2,2-雙[(4-胺基苯氧基)甲基]丙烷、2,2-雙[4-(4-胺基苯氧基)苯基]六氟丙烷、2,2-雙[4-(4-胺基
苯氧基)苯基]丙烷、雙[4-(3-胺基苯氧基)苯基]碸、雙[4-(4-胺基苯氧基)苯基]碸、1,1-雙(4-胺基苯基)環己烷、α,α’-雙(4-胺基苯基)-1,4-二異丙基苯、9,9-雙(4-胺基苯基)茀、2,2-雙(3-胺基苯基)六氟丙烷、2,2-雙(4-胺基苯基)六氟丙烷、4,4’-二胺基二苯基胺、2,4-二胺基二苯基胺、1,8-二胺基萘、1,5-二胺基萘、1,5-二胺基蒽醌、1,3-二胺基芘、1,6-二胺基芘、1,8-二胺基芘、2,7-二胺基茀、1,3-雙(4-胺基苯基)四甲基二矽氧烷、聯苯胺、2,2’-二甲基聯苯胺、1,2-雙(4-胺基苯基)乙烷、1,3-雙(4-胺基苯基)丙烷、1,4-雙(4-胺基苯基)丁烷、1,5-雙(4-胺基苯基)戊烷、1,6-雙(4-胺基苯基)己烷、1,7-雙(4-胺基苯基)庚烷、1,8-雙(4-胺基苯基)辛烷、1,9-雙(4-胺基苯基)壬烷、1,10-雙(4-胺基苯基)癸烷、1,3-雙(4-胺基苯氧基)丙烷、1,4-雙(4-胺基苯氧基)丁烷、1,5-雙(4-胺基苯氧基)戊烷、1,6-雙(4-胺基苯氧基)己烷、1,7-雙(4-胺基苯氧基)庚烷、1,8-雙(4-胺基苯氧基)辛烷、1,9-雙(4-胺基苯氧基)壬烷、1,10-雙(4-胺基苯氧基)癸烷、二(4-胺基苯基)丙烷-1,3-二酸酯(dioate)、二(4-胺基苯基)丁烷-1,4-二酸酯、二(4-胺基苯基)戊烷-1,5-二酸酯、二(4-胺基苯基)己烷-1,6-二酸酯、二(4-胺基苯基)庚烷-1,7-二酸酯、二(4-胺基苯基)辛烷-1,8-二酸酯、二(4-胺基苯基)壬烷-1,9-二酸酯、二(4-胺基苯基)癸烷-1,10-二酸酯、1,3-雙〔4-(4-胺基苯氧基)苯氧基〕丙烷、1,4-雙〔4-(4-胺基苯氧基)苯氧基〕丁烷、1,5-雙〔4-(4-胺基苯氧基)苯氧基〕戊烷、1,6-雙〔4-(4-胺基苯氧基)
苯氧基〕己烷、1,7-雙〔4-(4-胺基苯氧基)苯氧基〕庚烷、1,8-雙〔4-(4-胺基苯氧基)苯氧基〕辛烷、1,9-雙〔4-(4-胺基苯氧基)苯氧基〕壬烷、1,10-雙〔4-(4-胺基苯氧基)苯氧基〕癸烷等。
芳香族-脂肪族二胺之例方面,可舉例如3-胺基苄基胺、4-胺基苄基胺、3-胺基-N-甲基苄基胺、4-胺基-N-甲基苄基胺、3-胺基苯乙基胺、4-胺基苯乙基胺、3-胺基-N-甲基苯乙基胺、4-胺基-N-甲基苯乙基胺、3-(3-胺基丙基)苯胺、4-(3-胺基丙基)苯胺、3-(3-甲基胺基丙基)苯胺、4-(3-甲基胺基丙基)苯胺、3-(4-胺基丁基)苯胺、4-(4-胺基丁基)苯胺、3-(4-甲基胺基丁基)苯胺、4-(4-甲基胺基丁基)苯胺、3-(5-胺基戊基)苯胺、4-(5-胺基戊基)苯胺、3-(5-甲基胺基戊基)苯胺、4-(5-甲基胺基戊基)苯胺、2-(6-胺基萘基)甲基胺、3-(6-胺基萘基)甲基胺、2-(6-胺基萘基)乙基胺、3-(6-胺基萘基)乙基胺等。
雜環式二胺之例方面,可舉例如2,6-二胺基吡啶、2,4-二胺基吡啶、2,4-二胺基-1,3,5-三嗪、2,7-二胺基二苯並呋喃、3,6-二胺基咔唑、2,4-二胺基-6-異丙基-1,3,5-三嗪、2,5-雙(4-胺基苯基)-1,3,4-氧雜二唑等。
為得到本發明的聚醯胺,與二胺成分反應之二羧酸方面,以不具有芳香族環的二羧酸,例如脂肪族二羧酸或脂環式系的二羧酸為佳。如此之二羧酸或其衍生物的脂肪族二羧酸的具體例,可舉例如丙二酸、草酸、二甲基丙二酸、琥珀酸、富馬酸、戊二酸、己二酸、黏康酸、
2-甲基己二酸、三甲基己二酸、庚二酸、2,2-二甲基戊二酸、3,3-二乙基琥珀酸、杜鵑花酸、癸二酸及辛二酸等的二羧酸。
脂環式系的二羧酸方面,可舉例如1,1-環丙烷二羧酸、1,2-環丙烷二羧酸、1,1-環丁烷二羧酸、1,2-環丁烷二羧酸、1,3-環丁烷二羧酸、3,4-二苯基-1,2-環丁烷二羧酸、2,4-二苯基-1,3-環丁烷二羧酸、1-環丁烯-1,2-二羧酸、1-環丁烯-3,4-二羧酸、1,1-環戊烷二羧酸、1,2-環戊烷二羧酸、1,3-環戊烷二羧酸、1,1-環己烷二羧酸、1,2-環己烷二羧酸、1,3-環己烷二羧酸、1,4-環己烷二羧酸、1,4-(2-降冰片烯)二羧酸、降冰片烯-2,3-二羧酸、雙環[2.2.2]辛烷-1,4-二羧酸、雙環[2.2.2]辛烷-2,3-二羧酸、2,5-二側氧基-1,4-雙環[2.2.2]辛烷二羧酸、1,3-金剛烷二羧酸、4,8-二側氧基-1,3-金剛烷二羧酸、2,6-螺[3.3]庚烷二羧酸、1,3-金剛烷二乙酸、樟腦酸等。
又,製造本發明使用的聚醯胺時,在不損及本發明的效果範圍,可使用芳香族二羧酸或含雜環之二羧酸等。此時,芳香族二羧酸或含雜環之二羧酸之合計量,全二羧酸之合計量每100莫耳以10莫耳以下為佳。芳香族二羧酸或含雜環之二羧酸之含量過大,則N-烷氧基甲基改性時甲醛與芳香族環進行反應,有得到的樹脂的操作性、物性等降低之情形。
芳香族二羧酸方面,可舉例如o-苯二甲酸、間苯二甲酸、對苯二甲酸、5-甲基間苯二甲酸、5-tert-丁
基間苯二甲酸、5-胺基間苯二甲酸、5-羥基間苯二甲酸、2,5-二甲基對苯二甲酸、四甲基對苯二甲酸、1,4-萘二羧酸、2,5-萘二羧酸、2,6-萘二羧酸、2,7-萘二羧酸、1,4-蒽二羧酸、1,4-蒽醌二羧酸、2,5-聯苯基二羧酸、4,4’-聯苯基二羧酸、1,5-聯伸苯基二羧酸、4,4”-三聯苯基二羧酸、4,4’-二苯基甲烷二羧酸、4,4’-二苯基乙烷二羧酸、4,4’-二苯基丙烷二羧酸、2,2-雙(苯基)丙烷二羧酸、4,4’-二苯基六氟丙烷二羧酸、2,2-二苯基六氟丙烷-4,4’-二羧酸、4,4’-二苯基醚二羧酸、4,4’-聯苄基二羧酸、4,4’-茋二羧酸、4,4’-二苯乙炔二羧酸、4,4’-羰基二安息香酸、4,4’-二苯基碸二羧酸、4,4’-二苯基硫化物二羧酸、p-伸苯基二乙酸、3,3’-p-伸苯基二丙酸、4-羧基桂皮酸、p-伸苯基二丙烯酸、3,3’-[4,4’-(亞甲基二-p-伸苯基)]二丙酸、4,4’-[4,4’-(氧雙-p-伸苯基)]二丙酸、4,4’-[4,4’-(氧雙-p-伸苯基)]二丁酸、(異亞丙基二-p-伸苯基二氧基)二丁酸、雙(p-羧基苯基)二甲基矽烷等的二羧酸。
含雜環之二羧酸方面,可舉例如1,5-(9-側氧基茀)二羧酸、3,4-呋喃二甲酸、4,5-噻唑二羧酸、2-苯基-4,5-噻唑二羧酸、1,2,5-噻二唑-3,4-二羧酸、1,2,5-氧雜二唑-3,4-二羧酸、2,3-吡啶二羧酸、2,4-吡啶二羧酸、2,5-吡啶二羧酸、2,6-吡啶二羧酸、3,4-吡啶二羧酸、3,5-吡啶二羧酸等。
上述各種二羧酸可為酸二鹵化物或者無水之構造者。上述各種二羧酸之化合物亦有存在有異構物者,
但亦可為包含彼等之混合物。又,亦可併用2種以上的化合物。又,本發明使用的二羧酸類不限於上述例示化合物。
以二羧酸與二胺之聚縮合等製造聚醯胺之方法方面,可舉例如二羧酸二氯化物與二胺成分之反應或使二羧酸與二胺成分在適當縮合劑、鹼的存在下反應之方法。
具體上可藉由使二羧酸二氯化物與二胺在鹼與有機溶劑的存在下,-20℃~150℃、較佳為0℃~50℃中,進行30分鐘~24小時、較佳為1~4小時反應而合成。
前述鹼可使用吡啶、三乙基胺、4-二甲基胺基吡啶,為了反應穩定進行,以吡啶為佳。鹼的添加量,由為可易除去之量且易得到高分子聚物觀點來看,相對二羧酸二氯化物以2~4倍莫耳為佳。
在縮合劑存在下進行縮合聚合之場合,作為該縮合劑,可使用三苯基亞磷酸酯、二環己基碳二醯亞胺、1-乙基-3-(3-二甲基胺基丙基)碳二醯亞胺鹽酸鹽、N,N’-羰基二咪唑、二甲氧基-1,3,5-三嗪基甲基嗎啉鎓、O-(苯並三唑-1-基)-N,N,N’,N’-四甲基脲鎓四氟硼酸酯、O-(苯並三唑-1-基)-N,N,N’,N’-四甲基脲鎓六氟磷酸鹽、(2,3-二氫-2-硫酮基-3-苯並噁唑基)膦酸二苯基酯、4-(4,6-二甲氧基-1,3,5-三嗪-2-基)4-甲氧基嗎啉鎓氯化物n-水合物等。
又,使用上述縮合劑之方法中,藉由添加路易士酸作為添加劑,反應有效率地進行。路易士酸方面,以氯化鋰、溴化鋰等之鹵素原子化鋰為佳。路易士酸之添加量相對二羧酸以0.1~1.0倍莫耳量為佳。
二羧酸類與二胺成分之反應使用的有機溶劑方面,為溶解生成之聚醯胺者,則不特別限定。其具體例如以下。
可舉例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯烷酮、N-乙基-2-吡咯烷酮、N-甲基己內醯胺、二甲基亞碸、四甲基尿素、吡啶、二甲基碸、γ-丁內酯、異丙基醇、甲氧基甲基戊醇、二戊烯、乙基戊基酮、甲基壬基酮、甲基乙基酮、甲基異戊基酮、甲基異丙基酮、甲基溶纖劑、乙基溶纖劑、甲基溶纖劑乙酸酯、乙基溶纖劑乙酸酯、丁基卡必醇、乙基卡必醇、乙二醇、乙二醇單乙酸酯、乙二醇單異丙基醚、乙二醇單丁基醚、丙二醇、丙二醇單乙酸酯、丙二醇單甲基醚、丙二醇-tert-丁基醚、二丙二醇單甲基醚、二乙二醇、二乙二醇單乙酸酯、二乙二醇二甲基醚、二丙二醇單乙酸酯單甲基醚、二丙二醇單乙基醚、二丙二醇單乙酸酯單乙基醚、二丙二醇單丙基醚、二丙二醇單乙酸酯單丙基醚、3-甲基-3-甲氧基丁基乙酸酯、三丙二醇甲基醚、3-甲基-3-甲氧基丁醇、二異丙基醚、乙基異丁基醚、二異丁烯、戊基乙酸酯、丁基丁酯、丁基醚、二異丁基酮、甲基環己烯、丙基醚、二己基醚、二噁烷、n-己烷、n-戊烷、n-辛烷、二乙
基醚、環己酮、乙烯碳酸酯、丙烯碳酸酯、乳酸甲基酯、乳酸乙基酯、乙酸甲基酯、乙酸乙基酯、乙酸n-丁基酯、乙酸丙二醇單乙基醚、丙酮酸甲基酯、丙酮酸乙基酯、3-甲氧基丙酸甲基酯、3-甲氧基丙酸乙基酯、3-乙氧基丙酸甲基酯、3-乙氧基丙酸乙基酯、3-乙氧基丙酸、3-甲氧基丙酸、3-甲氧基丙酸丙基酯、3-甲氧基丙酸丁基酯、二甘醇二甲醚、4-羥基-4-甲基-2-戊酮、3-甲氧基-N,N-二甲基丙烷醯胺、3-乙氧基-N,N-二甲基丙烷醯胺、3-丁氧基-N,N-二甲基丙烷醯胺等。此等可單獨使用或混合使用。進一步即使為不溶解聚醯胺酸之溶劑,在生成的聚醯胺不析出的範圍,可與上述溶劑混合使用。
由單體及聚合物的溶解性,以N-甲基-2-吡咯烷酮、γ-丁內酯為佳,此等可為1種或2種以上混合使用。合成時之單體之合計濃度由不易引起聚合物的析出、且易得到高分子聚物觀點來看,以1~30質量%為佳、5~20質量%更佳。
較佳實施形態中,本發明處使用的聚醯胺為依據ISO307,在96%H2SO4中0.5%所測定的黏度(黏度數:VN)在約140~約270立方公分每公克(cm3/g)的範圍之脂肪族聚醯胺。
上述聚醯胺中,較佳聚醯胺方面,可舉例如尼龍-6、尼龍-11、尼龍-12、尼龍-66、尼龍-610、尼龍-612、尼龍-1010、尼龍-1212、尼龍-66/610、尼龍6/66、尼龍6/69、或此等之2種以上的組合所構成之群中選出的
聚醯胺。進一步較佳為H-(NH-(CH2)5-CO)n-OH(尼龍-6)單獨聚合物或共聚物、H-(NH-(CH2)6-HN-CO-(CH2)4-CO)n-OH(尼龍66)、H-(NH-(CH2)6-HN-CO-(CH2)8-CO)n-OH(尼龍610)、H-(NH-(CH2)6-HN-CO-(CH2)10-CO)n-OH(尼龍612)、H-(NH-(CH2)5-CO)-OH+H-(NH-(CH2)6-HN-CO-(CH2)4-CO)-OH(不規則配列)(尼龍6/66)、H-NH-(CH2)5-CO)-OH+H-(NH-(CH2)11-CO)-OH(不規則配列)(尼龍6/12)、及H-(NH-(CH2)5-CO)-OH+H-(NH-(CH2)6-HN-CO-(CH2)7-CO)-OH(不規則配列)(尼龍6/69)、以及包含上述聚醯胺之混合物之聚醯胺。
又尼龍6/66(聚醯胺6/66)為BASF公司以「Ultramid C4」及「Ultramid C35」之商品名、或宇部興產(股)以(UbeIndustries Ltd.)~「Ube5033FXD27」之商品名販售者。尼龍6(聚醯胺6)為例如E.I.du Pont de Nemours公司所販售者。
較佳之聚醯胺方面,有poly-ε-caplamide(尼龍-6)、聚六亞甲基己二醯二胺(尼龍66)、聚六亞甲基癸二醯胺(尼龍610)等,亦可為主鏈含其他脂肪族聚醯胺、脂環或者異節環之聚醯胺。
本說明書中使用的「脂肪族聚醯胺」之用語可指脂肪族聚醯胺、脂肪族共聚醯胺、及此等之摻混或混合物。
如此得到的聚醯胺或市售的聚醯胺,可以例如T.L.Cairns等(J.Am.Chem.Soc.,71,P651(1949))提案之方法於醯胺鍵的氮原子N導入烷氧基甲基或烷基硫甲基。
例如使聚醯胺之甲酸溶液與甲醛之醇或硫醇溶液作用後,注入水/丙酮混合液等之貧溶劑中,以氨中和,產生改性聚醯胺之沈澱物。又,工業上可藉由使上述聚醯在高溫、高壓下使用磷酸觸媒,直接與甲醛與醇或硫醇作用,製作改性聚醯胺。伴隨聚醯胺之氮原子N的取代度變大,樹脂的結晶性、熔點、彈性率降低,且溶解性、柔軟性增大。取代度雖可因反應條件在廣範圍選擇,但本發明中使用取代度為10~50莫耳%、較佳為20~40莫耳%者。該取代範圍者最可溶於醇且在溶液狀態安定性佳。比10莫耳%低者無法滿足溶劑溶解性或密著性、及體積電阻率中之特性。另一方面,取代度比50莫耳%高,則反應條件設定變得困難。醯胺鍵的氮原子的取代基的種類可因改性反應使用的溶劑而選擇,使用醇之場合,例如可得到具有甲氧基甲基、乙氧基甲基、異丁氧基甲基等者,使用硫醇之場合,例如可得到具有乙基硫甲基、異丁基硫甲基等者。因取代該上述改性聚醯胺樹脂的醯胺鍵的氮原子之極性基的機能,可使得到的樹脂的溶解度提升。
又,經N-烷氧基甲基化或N-烷基硫甲基化的聚醯胺方面,可使用市售者。如此之市售者方面,例如Nagasechemtex(股)之Tresin(登錄商標)薄片型F-30K、MF-30、EF-30T、Tresin水溶性型FS-350E5AS、(股)鉛市之FINE RESIN(登錄商標)FR-101、FR-101K、FR-104、FR-105、FR-301、EM-120、EM-220、EM-325、NK-1001、Finelex(登錄商標)SN-802、SN-803、FR-700E、
FR-750E、SG-2000等。
又本發明中,作為(B)成分以使用具有1,000~100,000的重量平均分子量之聚醯胺為佳。又本說明書中,重量平均分子量為以膠體滲透層析法(GPC)使用聚苯乙烯作為標準試料得到的值。
本實施形態之硬化膜形成組成物除上述(A)成分及(B),可含有作為(C)成分之交聯觸媒。
(C)成分的交聯觸媒方面,例如可為酸或熱酸產生劑。該交聯觸媒在使用本實施形態之硬化膜形成組成物的硬化膜之形成中,對熱硬化反應的促進有效。
作為(C)成分使用酸或熱酸產生劑之場合,(C)成分為含磺酸基化合物、鹽酸或其鹽、預烘烤或曝光後烘烤時熱分解而產生酸之化合物、即在溫度80℃~250℃進行熱分解而產生酸之化合物則不特別限制。
如此之化合物方面,例如鹽酸、以及甲烷磺酸、乙烷磺酸、丙烷磺酸、丁烷磺酸、戊烷磺酸、辛烷磺酸、苯磺酸、p-甲苯磺酸、樟腦磺酸、三氟甲烷磺酸、p-酚磺酸、2-萘磺酸、三甲苯磺酸、p-二甲苯-2-磺酸、m-二甲苯-2-磺酸、4-乙基苯磺酸、1H,1H,2H,2H-全氟辛烷磺酸、全氟(2-乙氧基乙烷)磺酸、五氟乙烷磺酸、九氟丁烷-1-磺酸、十二基苯磺酸等的磺酸或其水合物或鹽等。
又,因熱產生酸之化合物方面,例如雙(甲苯
磺醯基氧基)乙烷、雙(甲苯磺醯基氧基)丙烷、雙(甲苯磺醯基氧基)丁烷、p-硝基苄基對甲苯磺酸鹽、o-硝基苄基對甲苯磺酸鹽、1,2,3-伸苯基參(甲基磺酸酯)、p-甲苯磺酸吡啶鎓鹽、p-甲苯磺酸嗎啉鎓鹽、p-甲苯磺酸乙基酯、p-甲苯磺酸丙基酯、p-甲苯磺酸丁基酯、p-甲苯磺酸異丁基酯、p-甲苯磺酸甲基酯、p-甲苯磺酸苯乙基酯、氰甲基p-甲苯磺酸酯、2,2,2-三氟乙基p-甲苯磺酸酯、2-羥基丁基p-對甲苯磺酸鹽、N-乙基-4-甲苯磺醯胺、及下述式[TAG-1]~式[TAG-41]所表示之化合物等。
本發明的實施形態之硬化膜形成組成物中(C)成分之含量,相對(A)成分之化合物與(B)成分的醯胺基的氮原子之中至少一部份經烷氧基甲基化或烷基硫甲基化的聚醯胺的合計量100質量份,較佳為0.01質量份~10質量份、更佳為0.05質量份~8質量份、進一步較佳為0.1質量份~6質量份。交聯觸媒的含量相對上述合計量為0.01質量份以上,則可賦予充分熱硬化性與溶劑耐性,亦可賦予對曝光之高感度。又,藉由使交聯觸媒的含量相對上述合計量為10質量份以下,可使硬化膜形成組成物的保存安定性良好。
本發明除上述(A)~(C)成分,亦可含有(D)成分。(D)成
分為具有碳原子數2~5之羥基烷基酯基、烷氧基矽烷基、N-烷氧基甲基、羧基及酚性羥基之中至少一個的丙烯酸聚合物。藉由添加(D)成分,對溶劑之溶解性提升。(D)成分的較佳添加量,基於(A)成分與(B)成分之合計量的100質量份,為5質量份~100質量份、進一步較佳為10質量份~80質量份。
本發明中,作為丙烯酸聚合物,可適用使丙烯酸酯、甲基丙烯酸酯、苯乙烯、丙烯醯胺、甲基丙烯醯胺等的具有不飽和雙鍵之單體聚合而得到的聚合物。
(D)成分的具有碳原子數2~5之羥基烷基酯基、烷氧基矽烷基、N-烷氧基甲基、羧基及酚性羥基之中至少一個的丙烯酸聚合物為具有該構造之丙烯酸聚合物即可,構成丙烯酸聚合物之高分子的主鏈的骨架及側鏈的種類等不特別限定。
例如具有碳原子數2~5之羥基烷基酯基或烷氧基矽烷基之構造單位,較佳構造單位如下述式[D1]所表示。
又具有羧基或酚性羥基中至少一者之構造單位,較佳構造單位如下述式[D2]所表示。
進一步具有N-烷氧基甲基之構造單位,較佳構造單位如下述式[D3]所表示。
上述式中、X11、X12及X13,各自獨立為氫原子或甲基,Y1為碳原子數1~3之羥基烷基或碳原子數1~4的烷氧基矽烷基烷基,Y2為羧基或酚性羥基,Y3為(碳原子數1~6之烷氧基)甲基。
(D)成分的丙烯酸聚合物重量平均分子量以3,000~200,000為佳、4,000~150,000更佳、5,000~100,000再更佳。重量平均分子量超過200,000為過大者,則有對溶劑之溶解性降低且操作性降低之情形,重量平均分子量未達3,000為過小者,則有熱硬化時變得硬化不足、溶劑耐性及耐熱性降低之情形。
上述般(D)成分的丙烯酸聚合物的合成方法方面,以使具有碳原子數2~5之羥基烷基酯基、烷氧基矽烷基、N-烷氧基甲基、羧基及酚性羥基之中至少一個的單體共聚合之方法為簡便。
具有碳原子數2~5之羥基烷基酯基之單體方
面,例如2-羥基乙基甲基丙烯酸酯、2-羥基乙基丙烯酸酯、2-羥基丙基甲基丙烯酸酯、2-羥基丙基丙烯酸酯、4-羥基丁基甲基丙烯酸酯、4-羥基丁基丙烯酸酯。
具有羧基之單體方面,例如丙烯酸、甲基丙烯酸、乙烯基安息香酸。
具有酚性羥基之單體方面,例如p-羥基苯乙烯、m-羥基苯乙烯、o-羥基苯乙烯。
具有烷氧基矽烷基之單體方面,例如甲基丙烯醯氧基丙基三甲氧基矽烷、甲基丙烯醯氧基丙基三環氧基矽烷、丙烯醯基氧基丙基三甲氧基矽烷、丙烯醯基氧基丙基三環氧基矽烷。
具有N-烷氧基甲基之單體方面,可舉例如N-甲氧基甲基丙烯醯胺、N-甲氧基甲基甲基丙烯醯胺、N-丁氧基甲基丙烯醯胺、N-丁氧基甲基甲基丙烯醯胺、N-(異丁氧基甲基)丙烯醯胺、N-(異丁氧基甲基)甲基丙烯醯胺。
又,本發明中,得到(D)成分的丙烯酸聚合物時,在不損及本發明的效果範圍,上述單體外,可併用可與該單體共聚合之單體(以下,亦稱其他單體)。
該其他單體方面,例如丙烯酸酯化合物、甲基丙烯酸酯化合物、馬來醯亞胺化合物、丙烯醯胺化合物、丙烯腈、馬來酸酐、苯乙烯化合物及乙烯化合物等。
其他單體之具體例雖不特別限定,若舉例如此之單體之具體例,其如下。
丙烯酸酯化合物方面,例如甲基丙烯酸酯、
乙基丙烯酸酯、異丙基丙烯酸酯、苄基丙烯酸酯、萘基丙烯酸酯、蒽基丙烯酸酯、蒽基甲基丙烯酸酯、苯基丙烯酸酯、2,2,2-三氟乙基丙烯酸酯、tert-丁基丙烯酸酯、環己基丙烯酸酯、異冰片基丙烯酸酯、2-甲氧基乙基丙烯酸酯、甲氧基三乙二醇丙烯酸酯、2-乙氧基乙基丙烯酸酯、四氫糠基丙烯酸酯、3-甲氧基丁基丙烯酸酯、2-甲基-2-金剛烷基丙烯酸酯、γ-丁內酯丙烯酸酯、2-丙基-2-金剛烷基丙烯酸酯、8-甲基-8-三環癸基丙烯酸酯、8-乙基-8-三環癸基丙烯酸酯、2,3-二羥基丙基丙烯酸酯、二乙二醇單丙烯酸酯、己內酯2-(丙烯醯基氧基)乙基酯、聚(乙二醇)乙基醚丙烯酸酯及5-丙烯醯基氧基-6-羥基降冰片烯-2-羧酸-6-內酯等。
甲基丙烯酸酯化合物方面,例如甲基甲基丙烯酸酯、乙基甲基丙烯酸酯、異丙基甲基丙烯酸酯、苄基甲基丙烯酸酯、萘基甲基丙烯酸酯、蒽基甲基丙烯酸酯、蒽基甲基甲基丙烯酸酯、苯基甲基丙烯酸酯、2,2,2-三氟乙基甲基丙烯酸酯、tert-丁基甲基丙烯酸酯、環己基甲基丙烯酸酯、異冰片基甲基丙烯酸酯、2-甲氧基乙基甲基丙烯酸酯、甲氧基三乙二醇甲基丙烯酸酯、2-乙氧基乙基甲基丙烯酸酯、四氫糠基甲基丙烯酸酯、3-甲氧基丁基甲基丙烯酸酯、2-甲基-2-金剛烷基甲基丙烯酸酯、γ-丁內酯甲基丙烯酸酯、2-丙基-2-金剛烷基甲基丙烯酸酯、8-甲基-8-三環癸基甲基丙烯酸酯、8-乙基-8-三環癸基甲基丙烯酸酯、2,3-二羥基丙基甲基丙烯酸酯、二乙二醇單甲基丙烯
酸酯、己內酯2-(甲基丙烯醯氧基)乙基酯、聚(乙二醇)乙基醚甲基丙烯酸酯及5-甲基丙烯醯氧基-6-羥基降冰片烯-2-羧酸-6-內酯等。
馬來醯亞胺化合物方面,例如馬來醯亞胺、N-甲基馬來醯亞胺、N-苯基馬來醯亞胺及N-環己基馬來醯亞胺等。
苯乙烯化合物方面,例如苯乙烯、甲基苯乙烯、氯苯乙烯、溴苯乙烯、4-tert-丁基苯乙烯等的苯乙烯化合物。
乙烯基化合物方面,例如甲基乙烯基醚、苄基乙烯基醚、乙烯基萘、乙烯基蒽、乙烯基聯苯、乙烯基咔唑、2-羥基乙基乙烯基醚、苯基乙烯基醚及丙基乙烯基醚等。
其他單體方面,上述化合物中,以丙烯酸酯化合物、甲基丙烯酸酯化合物為佳、尤其甲基甲基丙烯酸酯(甲基丙烯酸甲基酯)在取得性及溶解性等點,為佳。
為了得到(D)成分的丙烯酸聚合物,使用上述其他單體之場合,該其他單體之使用量基於欲獲得(D)成分的丙烯酸聚合物使用的全單體之合計量,以5~100莫耳%為佳。上述其他單體之使用量過少之場合,有無法得到對液晶溶劑之所期望之耐性、即耐性降低之情形。
得到本發明使用的(D)成分的丙烯酸聚合物之方法不特別限制,例如藉由使上述單體與依期望之上述以外之其他單體與聚合起始劑等在共存之溶劑中,50~110℃
之溫度下聚合反應而得到。此時,使用的溶劑為溶解單體及聚合起始劑等者,則不特別限定。具體例方面,如後述<溶劑>之記載。
前述方法所得到的(D)成分的丙烯酸聚合物通常為溶解於溶劑之溶液之狀態。
又,使上述方法所得到的(D)成分的丙烯酸聚合物的溶液投入攪拌下之二乙基醚或水等進行再沈澱,將生成的沈澱物過濾.洗淨後,在常壓或減壓下進行常溫乾燥或加熱乾燥,可作成(D)成分的丙烯酸聚合物的粉體。藉由前述操作,可除去與(D)成分的丙烯酸聚合物共存之聚合起始劑及未反應的單體,結果可得到精製的(D)成分的丙烯酸聚合物的粉體。以一次的操作不能充分精製之場合,可使得到的粉體再溶解於溶劑,重複上述操作。
本發明中,(D)成分的丙烯酸聚合物可以粉體形態或者使精製的粉末再溶解於後述溶劑之溶液形態使用。
又,本發明中,(D)成分的丙烯酸聚合物可為複數種(D)成分的丙烯酸聚合物的混合物。
本實施形態之硬化膜形成組成物主要以溶解於溶劑之溶液狀態使用。此時使用之溶劑為可將(A)成分及(B)成分、(C)成分、其他因應必要之(D)成分及後述之其他添加劑溶解即可,其種類及構造等不特別限定。
溶劑的具體例方面,例如甲醇、乙醇、2-丙醇、1-丁醇、2-丁醇、乙二醇單甲基醚、乙二醇單乙基醚、甲基溶纖劑乙酸酯、乙基溶纖劑乙酸酯、二乙二醇單甲基醚、二乙二醇單乙基醚、丙二醇、丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、丙二醇丙基醚乙酸酯、甲苯、二甲苯、甲基乙基酮、環戊酮、環己酮、2-丁酮、3-甲基-2-戊酮、2-戊酮、2-庚酮、γ-丁內酯、2-羥基丙酸乙基酯、2-羥基-2-甲基丙酸乙基酯、乙氧基乙酸乙基酯、羥基乙酸乙基酯、2-羥基-3-甲基丁烷酸甲基酯、3-甲氧基丙酸甲基酯、3-甲氧基丙酸乙基酯、3-環氧基丙酸乙基酯、3-環氧基丙酸甲基酯、丙酮酸甲基酯、丙酮酸乙基酯、乙酸乙基酯、乙酸丁基酯、乳酸乙基酯、乳酸丁基酯、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、及N-甲基吡咯烷酮等。此等中,因(B)成分的溶解性高,以甲醇、乙醇、2-丙醇、丙二醇單甲基醚等的溶劑為佳。
此等之溶劑可1種單獨或2種以上組合使用,進而可與水混合使用。
進一步,本實施形態之硬化膜形成組成物在不損及本發明的效果範圍,因應必要,可含有增感劑、矽烷偶合劑、界面活性劑、流變學調整劑、顏料、染料、保存安定劑、消泡劑、抗氧化劑等。
例如增感劑在使用本實施形態之硬化膜形成
組成物,形成熱硬化膜後,有效促進光反應。
其他添加劑的一例之增感劑方面,例如二苯甲酮、蒽、蒽醌、噻噸酮等及其衍生物、以及硝基苯基化合物等。此等中,以二苯甲酮衍生物及硝基苯基化合物為佳。較佳之化合物的具體例,例如N,N-二乙基胺基二苯甲酮、2-硝基茀、2-硝基芴酮、5-硝基苊、4-硝基聯苯、4-硝基桂皮酸、4-硝基茋、4-硝基二苯甲酮、5-硝基吲哚等。尤其、以二苯甲酮之衍生物之N,N-二乙基胺基二苯甲酮為佳。
此等之增感劑不限於上述者。又,增感劑可單獨或2種以上的化合物組合併用。
本實施形態之硬化膜形成組成物中增感劑的較佳使用比例,相對(A)成分的化合物與(B)成分的醯胺基的氮原子之中至少一部份經烷氧基甲基化或烷基硫甲基化的聚醯胺之合計質量的100質量份,為0.1質量份~20質量份,更佳為0.2質量份~10質量份。該比例過小之場合,有無法充分得到作為增感劑之效果之情形,過大之場合有透過率的降低及產生塗膜粗糙之情形。
本實施形態之硬化膜形成組成物為(A)成分之低分子的光配向成分、(B)成分之醯胺基的氮原子之中至少一部份經烷氧基甲基化或烷基硫甲基化的聚醯胺及(C)成分之交聯觸媒溶解於溶劑者。進一步、本實施形態之硬化膜形
成組成物可含有作為(D)成分之具有碳原子數2~5之羥基烷基酯基、烷氧基矽烷基、N-烷氧基甲基、羧基及酚性羥基之中至少一個的丙烯酸聚合物。而,在不損及本發明的效果範圍,可含有其他添加劑。
(A)成分與(B)成分的搭配比,以質量比計(A)成分:(B)成分=5:95~60:40為佳。(B)成分之含量比上述數值範圍大的場合,液晶配向性易降低、過小的場合因溶劑耐性降低而配向性易降低。
本實施形態之硬化膜形成組成物的較佳例如下。
[1]:含有(A)成分與(B)成分的搭配比為以質量比計5:95~60:40且基於(A)成分與(B)成分之合計量的100質量份為0.01質量份~10質量份之(C)成分、溶劑之硬化膜形成組成物。
[2]:含有(A)成分與(B)成分的搭配比為以質量比計5:95~60:40且基於(A)成分與(B)成分之合計量的100質量份為0.01質量份~10質量份之(C)成分、且基於(A)成分與(B)成分之合計量的100質量份為5質量份~100質量份之(D)成分、溶劑之硬化膜形成組成物。
以溶液使用本實施形態之硬化膜形成組成物之場合的搭配比例、調製方法等如以下詳述。
本實施形態之硬化膜形成組成物中固形分的比例在各成分均勻溶解於溶劑範圍,雖不特別限定,為1質量%~80質量%,較佳為3質量%~60質量%,更佳為5質量
%~40質量%。在此,固形分係指由硬化膜形成組成物的全成分除去溶劑者。
本實施形態之硬化膜形成組成物的調製方法,不特別限定。調製法方面,例如於溶解於溶劑的(B)成分的溶液中將(A)成分及(C)成分以特定的比例混合、作成均勻的溶液之方法、或者在該調製法之適當階段中,因應必要進一步添加其他添加劑混合之方法。
本實施形態之硬化膜形成組成物的調製中,以溶劑中之聚合反應得到的聚合物或共聚物的溶液可直接使用。該場合,例如於(B)成分的溶液與前述同樣地加入(A)成分及(C)成分作成均勻的溶液。此時、以濃度調整為目的可進一步追加投入溶劑。此時,(B)成分的生成過程所使用的溶劑與硬化膜形成組成物的濃度調整使用的溶劑可為相同或相異。
又,調製的硬化膜形成組成物的溶液以使用孔徑為0.2μm左右之過濾器等過濾後、使用為佳。
以塗佈棒塗佈、旋轉塗佈、流動塗佈、輥塗佈、狹縫塗佈、繼狹縫塗佈後旋轉塗佈、噴墨塗佈、印刷等,將本實施形態之硬化膜形成組成物之溶液塗佈於基板(例如,矽/被覆二氧化矽之基板、氮化矽基板、被覆有金屬例如鋁、鉬、鉻等之基板、玻璃基板、石英基板、ITO基板等)或薄膜(例如三乙醯基纖維素(TAC)薄膜、環烯烴聚合物薄
膜、聚對苯二甲酸乙二酯薄膜、丙烯酸薄膜等樹脂薄膜)等之上形成塗膜,隨後,以加熱板或烘箱等加熱乾燥,可形成硬化膜。
至於加熱乾燥之條件只要不使由硬化膜形成之配向材之成分溶出於塗佈於其上之聚合性液晶溶液中之程度進行交聯反應(加熱硬化)即可,例如採用在溫度60℃至200℃,時間0.4分鐘至60分鐘之範圍中適當選擇之加熱溫度及加熱時間。加熱溫度及加熱時間較好為70℃至160℃,0.5分鐘至10分鐘。
使用本實施形態之硬化膜形成組成物形成之硬化膜之膜厚例如為0.05μm至5μm,可考慮使用之基板之階差或光學、電性質適當選擇。
如此形成之硬化膜可藉由進行偏光UV照射而可發揮作為配向材,亦即作為使液晶等具有液晶性之化合物配向之構件之功能。
偏光UV之照射方法通常使用150nm至450nm之波長之紫外光至可見光,在室溫或加熱狀態下自垂直或傾斜方向照射直線偏光而進行。
由本實施形態之硬化膜組成物形成之配向材由於具有耐溶劑性及耐熱性,故將由後述聚合性液晶溶液所成之相位差材料塗佈於該配向材上後,藉由加熱至液晶之相轉移溫度使相位差材料成為液晶狀態,於配向材上配向,之後,使成為配向狀態之相位差材料直接硬化,可形成具有光學異向性之層之相位差材。
至於相位差材料係使用例如具有聚合性基之液晶單體及含有其之組成物(亦即聚合性液晶溶液)等。而且,形成配向材之基板為薄膜時,具有本實施形態之相位差材之薄膜可使用作為相位差薄膜。形成此種相位差材之相位差材料有成為液晶狀態時,而於配向材上成為水平配向、膽甾醇相配向、垂直配向、混合配向等配向狀態者,可分別依據必要之相位差特性使用。
另外,製造3D顯示器所用之圖型化相位差材時,對由本實施形態之硬化膜組成物以上述方法形成之硬化膜,介隔線與間隔圖型之遮罩自特定基準,以例如+45度方向進行偏光UV曝光,接著卸除遮罩後以-45度之方向進行偏光UV曝光,得到形成有液晶之配向控制方向不同之2種液晶配向區域之配向材。隨後,塗佈由聚合性液晶溶液所成之上述相位差材料後,加熱至液晶之相轉移溫度使相位差材料成為液晶狀態,在配向材上配向。接著,使成為配向狀態之相位差材料直接硬化,分別複數、規則地配置相位差特性不同之2種相位差區域,可獲得圖型化相位差材。
又,使用具有上述般形成的本實施形態之配向材之2片基板,透過間隔件,兩基板上的配向材相互面向貼合後,於彼等之基板間注入液晶,亦可作成液晶配向之液晶顯示元件。
如此、本實施形態之硬化膜形成組成物可適用在各種相位差材(相位差薄膜)或液晶顯示元件等的製造。
以下,舉實施例將本實施形態進一步詳細說明,但本實施形態不限於此等實施例。
以下的實施例使用的縮寫的意思如下。
CIN1:4-(6-羥基己基氧基)桂皮酸甲基酯
CIN2:4-[4-(6-羥基己基氧基)苯甲醯基]桂皮酸第三丁基酯
FR-101:將(股)鉛市製低聚合度6尼龍之30%甲氧基甲基化的樹脂於20wt%乙醇溶液調製者
FR-103:將(股)鉛市製6尼龍共聚合聚醯胺的20%甲氧基甲基化的樹脂於20wt%乙醇溶液調製者
HMM:日本Cytec Industries(股)製Cymel303(六甲氧基甲基三聚氰胺)
EM-220:將(股)鉛市製低聚合度6尼龍之30%甲氧基甲基化的樹脂於20wt%乙醇溶液調製者
PTSA:p-甲苯磺酸.一水合物
MAA:甲基丙烯酸
MMA:甲基甲基丙烯酸酯
HEMA:2-羥基乙基甲基丙烯酸酯
AIBN:α,α’-偶氮雙異丁腈
PM:丙二醇單甲基醚
EtOH:乙醇
依據以下的合成例得到的丙烯酸共聚物的數平均分子量及重量平均分子量為使用日本分光(股)製GPC裝置(Shodex(登錄商標)管柱KF803L及KF8()4L),溶出溶劑四氫呋喃以流量1mL/分鐘在管柱中(管柱溫度40℃)流動使溶離之條件下測定。又,下述數平均分子量(以下,稱Mn。)及重量平均分子量(以下,亦稱Mw。)以聚苯乙烯換算值表示。
於1L四口燒瓶,加入4-溴-4’-羥基二苯甲酮80.0g、N,N-二甲基乙醯胺(DMAc)500mL、丙烯酸tert-丁基酯55.4g、三丁基胺(Bu3N)160.2g、乙酸鈀(Pd(OAc)2)1.29g、三(o-甲苯基)膦(P-(o-Tol)3)3.50g,在100℃邊加熱邊攪拌。反應完畢後、於2L之乙酸乙基酯中注入反應系,使用1N-鹽酸水溶液、飽和食鹽水進行萃取。於萃取的有機層加入無水硫酸鎂進行脫水乾燥,過濾無水硫酸鎂。將得到的濾液使用迴轉蒸發濃縮機進行溶劑餾去,得到109.4g的目的物CIN2-1(紅褐色黏體)。得到的CIN2-1不精製而用於後續反應。
於2L四口燒瓶,加入CIN2-1 93.4g、N,N-二甲基甲醯胺(DMF)1L、6-氯-1-己醇39.3g、碳酸鉀
(K2CO3)119.4g、碘化鉀(KI)4.8g,在100℃邊加熱邊攪拌。反應完畢後、於5L之水使反應系注入,以1N-鹽酸水溶液進行中和,使用乙酸乙基進行萃取。於萃取的有機層加入無水硫酸鎂進行脫水乾燥,過濾無水硫酸鎂。將得到的濾液使用迴轉蒸發濃縮機進行溶劑餾去。殘渣使用異丙醇/己烷=1/10,進行再結晶,得到CIN2(黃土色固體)113.8g。目的物以1H-NMR測定結果如以下所示。由該結果,確認得到的固體為目的之CIN2。
1H NMR(400MHz,[D6]-DMSO):δ7.86-7.88(d,2H),7.73-7.75(d,2H),7.69-7.71(d,2H),7.62-7.66(d,1H),7.08-7.10(d,2H),6.65-6.69(d,1H),4.35-4.37(t,1H),4.06-4.09(t,2H),3.37-3.42(q,2H),1.73-1.77(m,2H),1.50(s,9H),1.37-1.46(m,6H)。
使MAA 2.5g、MMA 9.2g、HEMA 5.0g、作為聚合觸媒之AIBN 0.2g溶於PM 50.7g,藉由在70℃進行20小時反應得到丙烯酸共聚物溶液(固形分濃度25質量%)(P1)。得到的丙烯酸共聚物的Mn為19,600、Mw為45,200。
以表1、2所示之組成調製實施例1~6、及比較例1~4的各硬化膜形成組成物,對其各自進行密著性、配向感度、圖型形成性、透過率的評估。
將實施例及比較例的各硬化膜形成組成物於無鹼玻璃、TAC薄膜、丙烯酸薄膜上,使用棒塗佈機,以Wet膜厚4μm塗佈後,在溫度100℃、60秒鐘、熱循環式烤箱中進行加熱乾燥,形成硬化膜。對該硬化膜使313nm的直線偏光以種種的曝光量(最大100mJ/cm2)垂直照射,形成配向材。於基板上的配向材上,將Merck(股)製的水平配向用聚合性液晶溶液使用棒塗佈機以Wet膜厚6μm進行塗佈,接著,在65℃、60秒鐘加熱板上進行預烘烤,形成膜厚1.0μm的塗膜。使該基板上的塗膜以300mJ/cm2曝光,製作相位差材。使製作的基板上的相位差材以一對偏光板挾持。觀察相位差材中相位差特性之表現狀況,以配向材表現液晶配向性所必要之偏光UV之曝光量為配向感度。
將實施例及比較例的各硬化膜形成組成物於無鹼玻璃、TAC薄膜、丙烯酸薄膜上,使用棒塗佈機以Wet膜厚4μm塗佈後,在溫度100℃、60秒鐘、熱循環式烤箱中進行加熱乾燥,形成硬化膜。對該硬化膜以313nm的直線偏光垂直20mJ/cm2照射。曝光後的基板上將Merck(股)製的水平配向用聚合性液晶溶液使用旋轉塗佈機進行塗佈,接著,在65℃、60秒鐘加熱板上進行預烘
烤,形成膜厚1.0μm的塗膜。使該薄膜以300mJ/cm2曝光,製作相位差材。於得到的基板上的相位差材使用美工刀切入方格(1mm×1mm×100棋盤方格),之後黏貼黏著膠帶(Nichiban(股)製Cellotape(登錄商標)),接著計算剝離該黏著膠帶時,基板上的膜未剝離而殘留的棋盤格個數,以[殘留棋盤格數/100]評估。膜未剝離且殘留棋盤格在90個以上者評估為密著性良好。
進行以上評估結果如下表2所示。
實施例1~6不因使用基板之種類而異,皆以少曝光量顯示液晶配向性,可得到具有優異的光反應效率與耐溶劑性之硬化膜(配向材)。
進一步得到的硬化膜不限基板之種類,對基板顯示高密著性。
另一方面,比較例1~4即使照射100mJ/cm2之直線偏光亦未配向,不能進行密著性之評估。
本發明之硬化膜形成組成物適用作為液晶顯示元件的液晶配向膜或於液晶顯示元件形成內部或外部設置的光學異方向性薄膜用的配向材,尤其宜用作為3D顯示器之圖型化相位差材的形成材料。進一步宜用作為形成薄膜電晶體(TFT)型液晶顯示元件或有機EL元件等之各種顯示器中保護膜、平坦化膜及絕緣膜等之硬化膜之材料、尤其形成TFT型液晶元件的層間絕緣膜、彩色濾光器之保護膜或有機EL元件的絕緣膜等之材料。
Claims (10)
- 一種硬化膜形成組成物,其特徵係含有(A)具有光配向性基、與由羥基、羧基、胺基及烷氧基矽烷基中選出之任1個取代基之化合物、(B)醯胺基的氮原子之中至少一部份經烷氧基甲基化或烷基硫甲基化的聚醯胺、及(C)交聯觸媒。
- 如請求項1記載的硬化膜形成組成物,其中,(A)成分的光配向性基為進行光二聚化或光異構化之構造之官能基。
- 如請求項1或請求項2記載的硬化膜形成組成物,其中,(A)成分的光配向性基為桂皮醯基。
- 如請求項1或請求項2記載的硬化膜形成組成物,其中,(A)成分的光配向性基為偶氮苯構造之基。
- 如請求項1~請求項4中任一項記載的硬化膜形成組成物,其中,(B)成分的聚醯胺為使尼龍-6、尼龍-11、尼龍-12、尼龍-66、尼龍-610、尼龍-612、尼龍-1010、尼龍-1212、尼龍-66/610、尼龍6/66、尼龍6/69、尼龍6-I/6-T、及此等之2種以上的組合所構成之群中選出的聚醯胺進行N-烷氧基甲基化或N-烷基硫甲基化者。
- 如請求項1~請求項5中任一項記載的硬化膜形成組成物,其中,(B)成分的聚醯胺為使聚醯胺進行N-烷氧 基甲基化者。
- 如請求項1~請求項6中任一項記載的硬化膜形成組成物,其中,進一步含有(D)具有碳原子數2~5之羥基烷基酯基、烷氧基矽烷基、N-烷氧基甲基、羧基及酚性羥基之中至少一個的丙烯酸聚合物。
- 如請求項1~請求項7中任一項記載的硬化膜形成組成物,其中,(B)成分的聚醯胺具有1,000~100,000的重量平均分子量。
- 一種配向材,其特徵係使用請求項1~請求項8中任一項記載的硬化膜形成組成物而得到。
- 一種相位差材,其特徵係使用請求項1~請求項8中任一項記載的硬化膜形成組成物所得到的硬化膜而形成。
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WO2015030000A1 (ja) | 2015-03-05 |
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CN105492535B (zh) | 2018-03-16 |
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