JP2018013532A - 光配向膜用ワニス及び液晶表示装置 - Google Patents
光配向膜用ワニス及び液晶表示装置 Download PDFInfo
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- JP2018013532A JP2018013532A JP2016141379A JP2016141379A JP2018013532A JP 2018013532 A JP2018013532 A JP 2018013532A JP 2016141379 A JP2016141379 A JP 2016141379A JP 2016141379 A JP2016141379 A JP 2016141379A JP 2018013532 A JP2018013532 A JP 2018013532A
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- Prior art keywords
- polyamic acid
- group
- skeleton
- varnish
- compound
- Prior art date
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- 239000002966 varnish Substances 0.000 title claims abstract description 42
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 37
- 230000003287 optical effect Effects 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 104
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 40
- 239000002253 acid Substances 0.000 claims abstract description 28
- 150000002148 esters Chemical class 0.000 claims abstract description 25
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 14
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 229920005575 poly(amic acid) Polymers 0.000 claims description 149
- -1 pyridine compound Chemical class 0.000 claims description 36
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 125000003277 amino group Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000000962 organic group Chemical group 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 11
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- 230000008569 process Effects 0.000 claims description 9
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- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
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- 239000002904 solvent Substances 0.000 claims description 7
- 238000006358 imidation reaction Methods 0.000 claims description 6
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
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- 125000001302 tertiary amino group Chemical group 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
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- 238000005576 amination reaction Methods 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
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- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
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- 230000001678 irradiating effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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Images
Classifications
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- 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
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Abstract
Description
すなわち、本発明の第1の側面に係る光配向膜用ワニスは、有機溶媒中に、イミド化促進剤と、ポリアミド酸又はポリアミド酸エステルである第1ポリアミド酸系化合物とを含む。第1ポリアミド酸系化合物は、第一級アミノ基を含まない末端骨格を有する。イミド化促進剤は、第一級アミノ基及び第二級アミノ基を含まない骨格を有する。
イミド化促進剤は、第1ポリアミド酸系化合物に対する脱水閉環反応を促進する。
本発明の第1ポリアミド酸系化合物は、上述の通り、末端骨格が式(3)、(4)又は(5)の何れかであることが好ましい。
上に述べたように、DC残像を実質的に生じさせないためのイミド化促進剤についての要件は、イミド化促進剤に第一級アミノ基及び第二級アミノ基以外の骨格を持たせないことであり、このことは究極的には、イミド化促進剤を実質的に用いないことにより達成することができる。しかし、イミド化促進剤を用いないと、イミド化を促進させることができないので、第1ポリアミド酸系化合物(第一級アミノ基を含まない末端骨格を有する)にイミド化を促進し得る骨格を導入する。
別の実施形態において、光配向膜用ワニスは、第1ポリアミド酸系化合物に加えて、ポリアミド酸又はポリアミド酸エステルである第2ポリアミド酸系化合物をさらに含む。その場合、第1ポリアミド酸系化合物は、第2ポリアミド酸系化合物よりも高い極性(大きな表面エネルギー)を有する。したがって、第1ポリアミド酸系化合物と第2ポリアミド酸系化合物とを共存させた場合、両者は相分離する。この場合、第1ポリアミド酸系化合物の方が、液晶表示装置における画素電極を形成するITO又はSiO2やSiNxのような無機パッシベーション膜又は有機樹脂を用いた有機パッシベーション膜との親和性が高いので、第1ポリアミド酸系化合物が下層となる。通常、ポリアミド酸エステルとポリアミド酸が共存する場合、ポリアミド酸エステルが上層を形成し、ポリアミド酸が下層を形成する。また、2種のポリアミド酸が共存する場合であって、一方のポリアミド酸のジアミン骨格に酸素又はフッ素が存在し、他方のポリアミド酸のジアミン骨格に酸素及びフッ素のいずれも存在しない場合、上記一方のポリアミド酸が下層を形成し、上記他方のポリアミド酸が上層を形成する。また、上記他方のポリアミド酸に酸素又はフッ素が存在していてもその量が上記一方のポリアミド酸のジアミン骨格における酸素又はフッ素の量よりも少ない場合も、上記一方のポリアミド酸が下層を形成し、上記他方のポリアミド酸が上層を形成する。
イミド化後の膜に、光配向処理を行って、配向膜を提供する。光配向処理は、波長254nm又は365nmの短波長紫外光を膜に照射することによって行うことができる。
本発明の第3の側面によると、本発明の光配向膜用ワニスのイミド化物を含む配向膜を備える液晶表示装置が提供される。
1,3−ジメチル−1,2,3,4−シクロブタンテトラカルボン酸二無水物100モル部のN−メチル−2−ピロリドン(NMP)溶液と、p−フェニレンジアミン110モル部のNMP溶液を混合し、室温で8時間反応させて、第一級アミンを両末端に有するポリアミド酸を生成させた。この反応混合物に、N,N−ジメチルホルムアミドジメチルアセタール100モル部を滴下し、50℃で2時間反応させて、各酸骨格中の2個のカルボキシル基をメチルエステル化させた。得られた反応混合物に、フタル酸無水物5モル部のNMP溶液を添加し、室温で8時間反応させて、ポリアミド酸の両末端第一級アミノ基をアミド酸として封止した。未反応のモノマー、低分子量成分を除去して、固形分濃度15質量%の所望の両末端封止ポリアミド酸エステル溶液を得た。
ピロメリット酸二無水物100モル部のNMP溶液と、4,4’−ジアミノジフェニルエーテル110モル部のNMP溶液を混合し、室温で8時間反応させて、第一級アミンを両末端に有するポリアミド酸を生成させた。この反応混合物に、フタル酸無水物5モル部のNMP溶液を添加し、室温で8時間反応させて、ポリアミド酸の両末端第一級アミノ基をアミド酸として封止した。未反応のモノマー、低分子量成分を除去して、固形分濃度15質量%のポリアミド酸溶液を得た。
合成例1において、p−フェニレンジアミンの代わりに、4−[(4−アミノフェニル)メチル]アニリンを用いた以外は、合成例1と同様の手法により、両末端第一級アミノ基をアミド化したポリアミド酸溶液を得た。
1,3−ジメチル−1,2,3,4−シクロブタンテトラカルボン酸二無水物100モル部のNMP溶液と、p−フェニレンジアミン90モル部のNMP溶液を混合し、室温で8時間反応させて、カルボキシル基を両末端に有するポリアミド酸を生成させた。未反応のモノマー、低分子量成分を除去して、固形分濃度15質量%のポリアミド酸溶液を得た。
ピロメリット酸二無水物100モル部のNMP溶液と、4,4’−ジアミノジフェニルエーテル90モル部のNMP溶液を混合し、室温で8時間反応させて、カルボキシル基を両末端に有するポリアミド酸を生成させた。未反応のモノマー、低分子量成分を除去して、固形分濃度15質量%のポリアミド酸溶液を得た。
合成例1において、p−フェニレンジアミンの代わりに、上の式(G)で示されるジアミンを用いた以外は、合成例1と同様の手法により、両末端第一級アミノ基をアミド化したポリアミド酸溶液を得た。
合成例1において、p−フェニレンジアミンの代わりに、上の式(F)で示されるジアミンを用いた以外は、合成例1と同様の手法により、両末端第一級アミノ基をアミド化したポリアミド酸溶液を得た。
下記表2−1、表2−2及び表2−3に示す実施例1〜10及び比較例1〜4の各ポリアミド酸系化合物には、当該表に示すようなイミド化促進剤をそれぞれ加え(加えない場合もある)、均一になるように撹拌し、上層成分及び下層成分を質量比1:1で混合して塗布液を調製した。図1に示す構造の液晶表示装置のアレイ基板及び対向基板の配向膜113を塗布すべき領域に各塗布液を塗布し、200℃に加熱してイミド化を行った。イミド化率は、いずれも80%であった。各イミド化膜に対し、短波長の紫外光を用いて光配向処理を行った。各配向膜を洗浄した後、こうして配向膜を形成したアレイ基板及び対向基板を用いて常法により図1に示す構造の表示パネルを備える液晶表示装置を作製した。液晶としては、誘電異方性がΔεが負でその値が−4.1(1kHz,20℃)であり、屈折率異方性Δnが0.0821(波長590nm,20℃)のネマチック液晶材料(メルク社製MLC−2039)を用いた。
{(a−b)/b}×100
(式中、aは、白表示部の輝度であり、bは、黒表示部の輝度である)を残像強度とした。この数値が1%以上あると、人間の目には残像として認識される。
A:グレー表示初期より残像は発生しなかった。
B:グレー表示初期で斜めから見たらかろうじて見える残像が発生し、1時間以内に消失した。
C:グレー表示初期で正面から目視可能な残像が発生し、1時間以内に消失した。
D:グレー表示初期で正面から目視可能な残像が発生し、1時間後には斜めから見たらかろうじて見える残像に低減した。
E:グレー表示初期で正面から目視可能な残像が発生し、1時間後も消失しなかった。
A:1000時間までに表示むらは発生しなかった。
B:750時間までに表示むらは発生せず、1000時間後に直径1mm以下の小さな輝度むら(表示むら)が基板外周の一部に発生した。
C:500時間までに表示むらは発生せず、1000時間後に直径1mm以上の、一目で視認可能な大きさの輝度むらが基板外周の一部に発生した。
D:500時間までに直径1mm以下の小さな輝度むらが基板外周の一部に発生した。
E:500時間までに直径1mm以上の、一目で視認可能な大きさの輝度むらが基板外周の一部に発生した。
Claims (13)
- 有機溶媒中に、イミド化促進剤と、ポリアミド酸又はポリアミド酸エステルである第1ポリアミド酸系化合物とを含み、
前記イミド化促進剤は、第一級アミノ基及び第二級アミノ基を含まない骨格を有し、
前記第1ポリアミド酸系化合物は、第一級アミノ基を含まない末端骨格を有することを特徴とする光配向膜用ワニス。 - 前記イミド化促進剤は、ピリジン系化合物、キノリン系化合物、イソキノリン系化合物、イミダゾ−ル系化合物、若しくはベンゾイミダゾ−ル系化合物、又は第三級アミンであることを特徴とする請求項1に記載の光配向膜用ワニス。
- 前記イミド化促進剤が、アミン反応性骨格を有することを特徴とする請求項1又は請求項2に記載の光配向膜用ワニス。
- 前記アミン反応性骨格は、ハロゲン基、ジアゾ基、カルボキシル基、ヒドロキシル基、イソシアネート基、又は酸無水物骨格のいずれかであることを特徴とする請求項3に記載の光配向膜用ワニス。
- 前記イミド化促進剤は、130以上の分子量を有することを特徴とする請求項1から請求項4までのいずれか1項に記載の光配向膜用ワニス。
- 前記末端骨格が、イミド骨格、アミド骨格、ウレア骨格、第三級アミノ骨格、アゾ結合又はカルボキシル基を有することを特徴とする請求項1から請求項9までのいずれか1項に記載の光配向膜用ワニス。
- ポリアミド酸又はポリアミド酸エステルである第2ポリアミド酸系化合物をさらに含み、前記第1ポリアミド酸系化合物は、前記第2ポリアミド酸系化合物よりも高い極性を有することを特徴とする請求項1から請求項10までのいずれか1項に記載の光配向膜用ワニス。
- 請求項1から請求項11までに記載の光配向膜用ワニスのイミド化物を含む配向膜を備える液晶表示装置。
- 請求項1から請求項11までに記載の光配向膜用ワニスを用いて光配向膜を形成する工程と、前記光配向膜を有機溶媒又は酸化性溶媒を用いて洗浄をする工程とを有することを特徴とする光配向膜の製造方法。
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