JP2020519947A - 液晶配向剤組成物、これを用いた液晶配向膜の製造方法、およびこれを用いた液晶配向膜 - Google Patents
液晶配向剤組成物、これを用いた液晶配向膜の製造方法、およびこれを用いた液晶配向膜 Download PDFInfo
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- JP2020519947A JP2020519947A JP2019561771A JP2019561771A JP2020519947A JP 2020519947 A JP2020519947 A JP 2020519947A JP 2019561771 A JP2019561771 A JP 2019561771A JP 2019561771 A JP2019561771 A JP 2019561771A JP 2020519947 A JP2020519947 A JP 2020519947A
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- 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
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 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
- 239000000428 dust Substances 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
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 230000008642 heat stress Effects 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
- 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
- 239000012535 impurity Substances 0.000 description 1
- 230000001939 inductive effect Effects 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 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
- 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
- 229920001778 nylon Polymers 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
- 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 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
- 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
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007650 screen-printing 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
- HUAUNKAZQWMVFY-UHFFFAOYSA-M sodium;oxocalcium;hydroxide Chemical compound [OH-].[Na+].[Ca]=O HUAUNKAZQWMVFY-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 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
- 239000004094 surface-active agent Substances 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
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
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Abstract
Description
下記化学式4で表される繰り返し単位、下記化学式5で表される繰り返し単位および下記化学式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;
を含む、液晶配向剤組成物が提供される。
R1、R2、R3、およびR4は、それぞれ独立して水素またはC1−10アルキルであり、ただしR1およびR2はいずれも水素ではなく、R3およびR4がいずれも水素ではなく、
X1は、下記化学式7で表される4価の有機基であり、
[化学式7]
R5、R6、R7、およびR8は、それぞれ独立して水素、またはC1−6アルキルであり、
X2、X3、X4、X5、およびX6は、それぞれ独立して炭素数4〜20の炭化水素に由来した4価の有機基であるか、あるいは前記4価の有機基のうち一つ以上のHがハロゲンに置換されるかまたは一つ以上の−CH2−が酸素または硫黄原子が直接連結されないように−O−、−CO−、−S−、−SO−、−SO2−または−CONH−に代替された4価の有機基であり、
前記化学式1〜3において、
Y1〜Y3は、それぞれ独立して下記化学式8で表される2価の有機基であり、
[化学式8]
R9およびR10は、それぞれ独立してハロゲン、シアノ、C1−10アルキル、C2−10アルケニル、C1−10アルコキシ、C1−10フルオロアルキル、またはC1−10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、
L1は、単一結合、−O−、−CO−、−S−、−SO2−、−C(CH3)2−、−C(CF3)2−、−CONH−、−COO−、−(CH2)z−、−O(CH2)zO−、−O(CH2)z−、−OCH2−C(CH3)2−CH2O−、−COO−(CH2)z−OCO−、または−OCO−(CH2)z−COO−であり、ここで、zは1〜10の整数であり、
kおよびmは、それぞれ独立して1〜3の整数であり、
nは、0〜3の整数であり、
前記化学式4〜6において、
Z1、Z2、およびZ3は、それぞれ独立して下記化学式9で表される2価の有機基であり、
[化学式9]
A1は、16族元素であり、
R11は、水素、またはC1−10アルキルであり、
aは、0〜3の整数であり、
A2、A3、A4、およびA5は、窒素または炭素であり、ただしA2〜A5のうち少なくとも一つは窒素であり、残りは炭素である。
R18およびR19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、
X7〜X9は、それぞれ独立して4価の有機基であり、
Z4〜Z6は、それぞれ独立して下記化学式16で表される2価の有機基であり、
[化学式16]
R20およびR21は、それぞれ独立してハロゲン、シアノ、C1−10アルキル、C2−10アルケニル、C1−10アルコキシ、C1−10フルオロアルキル、またはC1−10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、
L4は、単一結合、−O−、−CO−、−S−、−SO2−、−C(CH3)2−、−C(CF3)2−、−CONH−、−COO−、−(CH2)z−、−O(CH2)zO−、−O(CH2)z−、−OCH2−C(CH3)2−CH2O−、−COO−(CH2)z−OCO−、または−OCO−(CH2)z−COO−であり、ここで、zは、それぞれ独立して1〜10の整数であり、
k'およびm'は、それぞれ独立して0〜3の整数であり、
n'は、0〜3の整数である。
L5は、単結合、−O−、−SO2−、または−CR22R23−であり、ここで、R22およびR23は、それぞれ独立して水素、またはC1−10アルキルである。
Claims (17)
- 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2種以上の繰り返し単位を含み、
下記の化学式1〜3で表される全体繰り返し単位に対し、下記の化学式1で表される繰り返し単位を5〜74モル%含む
第1液晶配向剤用重合体;および
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;
を含む、
液晶配向剤組成物:
[化学式1]
R1、R2、R3、およびR4は、それぞれ独立して水素またはC1−10アルキルであり、ただしR1およびR2がいずれも水素ではなく、R3およびR4がいずれも水素ではなく、
X1は、下記の化学式7で表される4価の有機基であり、
[化学式7]
R5、R6、R7、およびR8は、それぞれ独立して水素、またはC1−6アルキルであり、
X2、X3、X4、X5、およびX6は、それぞれ独立して炭素数4〜20の炭化水素に由来した4価の有機基であるか、あるいは前記4価の有機基のうち一つ以上のHがハロゲンに置換されるかまたは一つ以上の−CH2−が酸素または硫黄原子が直接連結されないように−O−、−CO−、−S−、−SO−、−SO2−または−CONH−に代替された4価の有機基であり、
前記化学式1〜3において、
Y1〜Y3は、それぞれ独立して下記の化学式8で表される2価の有機基であり、
[化学式8]
R9およびR10は、それぞれ独立してハロゲン、シアノ、C1−10アルキル、C2−10アルケニル、C1−10アルコキシ、C1−10フルオロアルキル、またはC1−10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、
L1は、単一結合、−O−、−CO−、−S−、−SO2−、−C(CH3)2−、−C(CF3)2−、−CONH−、−COO−、−(CH2)z−、−O(CH2)zO−、−O(CH2)z−、−OCH2−C(CH3)2−CH2O−、−COO−(CH2)z−OCO−、または−OCO−(CH2)z−COO−であり、ここで、zは1〜10の整数であり、
kおよびmは、それぞれ独立して1〜3の整数であり、
nは、0〜3の整数であり、
前記化学式4〜6において、
Z1、Z2、およびZ3は、それぞれ独立して下記の化学式9で表される2価の有機基であり、
[化学式9]
A1は、16族元素であり、
R11は、水素、またはC1−10アルキルであり、
aは、0〜3の整数であり、
A2、A3、A4、およびA5は、窒素または炭素であり、ただしA2〜A5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X2、X3、X4、X5、およびX6は、それぞれ独立して下記の化学式10に記載された4価の有機基である、
請求項1に記載の液晶配向剤組成物:
[化学式10]
R5、R6、R7、およびR8は、それぞれ独立して水素、またはC1−6アルキルであり、
R12およびR13は、それぞれ独立して水素、またはC1−10アルキルであり、
L2は、単結合、−O−、−CO−、−S−、−SO−、−SO2−、−CR14R15−、−CONH−、−COO−、−(CH2)b−、−O(CH2)bO−、−COO−(CH2)b−OCO−、−HN−(CH2)b−NH−、−R14N−(CH2)b−NR15−、フェニレン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、
ここで、R14およびR15は、それぞれ独立して水素、C1−10アルキル、またはC1−10フルオロアルキルであり、
bは、それぞれ独立して1〜10の整数である。 - 前記化学式8は、下記の化学式11または化学式12である、
請求項1または2に記載の液晶配向剤組成物:
[化学式11]
L3は、単結合、−O−、−SO2−、または−CR16R17−であり、ここで、
R16およびR17は、それぞれ独立して水素、またはC1−10アルキルである。 - 前記化学式9において、
A2〜A5のうち一つが窒素であり、残りは炭素である、
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9において、
A2またはA5のうち一つが窒素であり、残りは炭素であり、
A3およびA4は炭素である、
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9において、
A1は酸素であり、
aは0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9は、下記の化学式9−1、化学式9−2および化学式9−3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、
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:
[化学式9−1]
A1〜A5、R11、aは、請求項1で定義したとおりである。 - 第1液晶配向剤用重合体と第2液晶配向剤用重合体は、5:95〜95:5の重量比で含まれる、
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。 - 前記第2液晶配向剤用重合体は、下記の化学式13で表される繰り返し単位、下記の化学式14で表される繰り返し単位および下記の化学式15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さらに含む、
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:
[化学式13]
R18およびR19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、
X7〜X9は、それぞれ独立して4価の有機基であり、
Z4〜Z6は、それぞれ独立して下記の化学式16で表される2価の有機基であり、
[化学式16]
R20およびR21は、それぞれ独立してハロゲン、シアノ、C1−10アルキル、C2−10アルケニル、C1−10アルコキシ、C1−10フルオロアルキル、またはC1−10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、
L4は、単一結合、−O−、−CO−、−S−、−SO2−、−C(CH3)2−、−C(CF3)2−、−CONH−、−COO−、−(CH2)z−、−O(CH2)zO−、−O(CH2)z−、−OCH2−C(CH3)2−CH2O−、−COO−(CH2)z−OCO−、または−OCO−(CH2)z−COO−であり、ここで、
zは、それぞれ独立して1〜10の整数であり、
k'およびm'は、それぞれ独立して0〜3の整数であり、
n'は0〜3の整数である。 - 前記化学式16は、下記の化学式17または化学式18である、
請求項9に記載の液晶配向剤組成物:
[化学式17]
L5は単結合、−O−、−SO2−、または−CR22R23−であり、ここで、
R22およびR23は、それぞれ独立して水素、またはC1−10アルキルである。 - 請求項1から10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に塗膜に光を照射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11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11または12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光照射は、150〜450nm波長の偏光した紫外線を照射することである、
請求項11から13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熱処理温度は、150〜300℃である、
請求項11から14のいずれか1項に記載の液晶配向膜の製造方法。 - 請求項11から15のいずれか1項に記載の液晶配向膜の製造方法により製造された、
液晶配向膜。 - 請求項16に記載の液晶配向膜を含む
液晶表示素子。
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