JP2020516952A - 液晶配向剤組成物、それを用いた液晶配向膜の製造方法、それを用いた液晶配向膜および液晶表示素子 - Google Patents
液晶配向剤組成物、それを用いた液晶配向膜の製造方法、それを用いた液晶配向膜および液晶表示素子 Download PDFInfo
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000004976 cyclobutylene group Chemical group 0.000 description 1
- 125000004977 cycloheptylene group Chemical group 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004978 cyclooctylene group Chemical group 0.000 description 1
- 125000004979 cyclopentylene group Chemical group 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000004980 cyclopropylene group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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Abstract
Description
X1〜X9は、それぞれ独立して下記化学式10で表される4価の有機基であり、
[化学式10]
Y7〜Y9は、それぞれ独立して下記化学式11で表される2価の有機基であり、
[化学式11]
Y1〜Y3は、それぞれ独立して下記化学式12で表される2価の有機基であり、
[化学式12]
Y4〜Y6は、それぞれ独立して下記化学式13で表される2価の有機基であり、
[化学式13]
L3は、単結合、−O−、−SO2−、−O(CH2)yO−または−CR17R18−であり、ここで、yは、1〜10の整数であり、R17およびR18は、それぞれ独立して水素、または炭素数1〜10のアルキルである。
Claims (15)
- 下記の化学式1で表される繰り返し単位、下記の化学式2で表される繰り返し単位および下記の化学式3で表される繰り返し単位からなる群より選ばれた1種以上の繰り返し単位を含む第1液晶配向剤用重合体;
下記の化学式4で表される繰り返し単位、下記の化学式5で表される繰り返し単位および下記の化学式6で表される繰り返し単位からなる群より選ばれた1種以上の繰り返し単位を含む第2液晶配向剤用重合体;および
下記の化学式7で表される繰り返し単位、下記の化学式8で表される繰り返し単位および下記の化学式9で表される繰り返し単位からなる群より選ばれた1種以上の繰り返し単位を含む第3液晶配向剤用重合体;
を含む、
液晶配向剤組成物:
[化学式1]
R1およびR2のうち少なくとも一つは、炭素数1〜10のアルキル基であり、残りは水素であり、
R3およびR4のうち少なくとも一つは、炭素数1〜10のアルキル基であり、残りは水素であり、
R5およびR6のうち少なくとも一つは、炭素数1〜10のアルキル基であり、残りは水素であり、
X1〜X9は、それぞれ独立して下記の化学式10で表される4価の有機基であり、
[化学式10]
R7〜R12は、それぞれ独立して水素または炭素数1〜6のアルキル基であり、
L1は、単結合、−O−、−CO−、−COO−、−S−、−SO−、−SO2−、−CR13R14−、−(CH2)Z−、−O(CH2)ZO−、−COO(CH2)ZOCO−、−CONH−、フェニレン基またはこれらの組み合わせからなる群より選ばれたいずれか一つであり、
前記R13およびR14は、それぞれ独立して水素、炭素数1〜10のアルキル基またはフルオロアルキル基であり、
zは、1〜10の整数であり、
Y7〜Y9は、それぞれ独立して下記の化学式11で表される2価の有機基であり、
[化学式11]
R15およびR16は、それぞれ独立して水素、ハロゲン、シアノ、ニトリル、炭素数1〜10のアルキル、炭素数1〜10のアルケニル、炭素数1〜10のアルコキシ、炭素数1〜10のフルオロアルキル、または炭素数1〜10のフルオロアルコキシであり、
pおよびqは、それぞれ独立して0〜4の整数であり、
L2は、単結合、−O−、−CO−、−S−、−SO2−、−C(CH3)2−、−C(CF3)2−、−COO−、−(CH2)y−、−O(CH2)yO−、−O(CH2)y−、−NH−、−NH(CH2)y−NH−、−NH(CH2)yO−、−OCH2−C(CH3)2−CH2O−、−COO−(CH2)y−OCO−、または−OCO−(CH2)y−COO−であり、
yは、1〜10の整数であり、
kおよびmは、それぞれ独立して0〜1の整数であり、
nは、0〜3の整数であり、
Y1〜Y3は、それぞれ独立して下記の化学式12で表される2価の有機基であり、
[化学式12]
Tは、前記化学式10で表される4価の有機基であり、
D1およびD2は、それぞれ独立して炭素数1〜20のアルキレン基、炭素数1〜10のヘテロアルキレン基、炭素数3〜20のシクロアルキレン基、炭素数6〜20のアリーレン基または炭素数2〜20のヘテロアリーレン基であり、
Y4〜Y6は、それぞれ独立して下記の化学式13で表される2価の有機基であり、
[化学式13]
Aは、15族元素であり、
R'は、水素、または炭素数1〜10のアルキルであり、
aは、1〜3の整数であり、
Z1〜Z4のうち少なくとも一つは窒素であり、残りは炭素である。 - 前記化学式13において、
Z1〜Z4のうち一つが窒素であり、残りは炭素である、
請求項1に記載の液晶配向剤組成物。 - 前記化学式13において、
Z1〜Z4のうち一つが窒素であり、残りは炭素であり、
Z2およびZ4は炭素である、
請求項1に記載の液晶配向剤組成物。 - 前記化学式13において、
Aは窒素であり、
R'は、水素であり、
aは、1である、
請求項1から3のいずれか1項に記載の液晶配向剤組成物。 - 前記化学式13は、下記の化学式13−1、化学式13−2および化学式13−3からなる群より選ばれた1種以上の官能基を含む、
請求項1から4のいずれか1項に記載の液晶配向剤組成物:
[化学式13−1]
A、Z1〜Z4、R'、aは、請求項1で定義したとおりである。 - 前記化学式12において、
Tは、下記の化学式10−1または10−2であり、
D1およびD2は、それぞれ独立してフェニレン基である、
請求項1から5のいずれか1項に記載の液晶配向剤組成物:
[化学式10−1]
- 前記第1液晶配向剤用重合体の100重量部に対して第2液晶配向剤用重合体の含有量が10重量部〜1000重量部である、
請求項1から6のいずれか1項に記載の液晶配向剤組成物。 - 前記第1液晶配向剤用重合体の100重量部に対して第3液晶配向剤用重合体の含有量が10重量部〜1000重量部である、
請求項1から7のいずれか1項に記載の液晶配向剤組成物。 - 請求項1から8のいずれか一項に記載の液晶配向剤組成物を基板に塗布して塗膜を形成する段階;
前記塗膜を乾燥する段階;
前記乾燥する段階の直後の塗膜に光を照射するかラビング処理して配向処理する段階;および
前記配向処理した塗膜を熱処理して硬化する段階
を含む、
液晶配向膜の製造方法。 - 前記液晶配向剤組成物は、有機溶媒に溶解または分散させたものである、
請求項9に記載の液晶配向膜の製造方法。 - 前記塗膜を乾燥する段階は、50℃〜150℃で行われる、
請求項9または10に記載の液晶配向膜の製造方法。 - 前記配向処理する段階での光照射は、150nm〜450nm波長の偏光した紫外線を照射することである、
請求項9から11のいずれか1項に記載の液晶配向膜の製造方法。 - 前記塗膜を硬化する段階での熱処理温度は、150℃〜300℃である、
請求項9から12のいずれか1項に記載の液晶配向膜の製造方法。 - 請求項1から8のいずれか1項に記載の液晶配向剤組成物の配向硬化物を含む、
液晶配向膜。 - 請求項14に記載の液晶配向膜を含む、
液晶表示素子。
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