IP Library Granted Patent US 11,312,906
Granted Patent B2
US 11,312,906 · App. 16/611,753 · Granted Apr 26, 2022

Polymerizable monomer, liquid crystal composition using polymerizable monomer, and liquid crystal display device

Inventors: Junichi Mamiya (Kita-adachi-gun, JP); Yuichi Inoue (Kita-adachi-gun, JP); Masaomi Kimura (Kita-adachi-gun, JP); Junko Yamamoto (Kita-adachi-gun, JP); Masanao Hayashi (Kita-adachi-gun, JP); Hirokazu Sugiyama (Kita-adachi-gun, JP)
Assignee: DIC CORPORATION
C09K19/12C09K19/32C09K19/3402G02F1/1337G02F1/1343B32B2457/20B32B2457/202C09K2019/0448C09K2019/122C09K2019/3425C09K2323/00
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Quick Facts
Patent No.
US 11,312,906
App. No.
16/611,753
Granted
Apr 26, 2022
Kind
B2
Abstract

A problem to be solved by the present invention is to provide a liquid crystal composition excellent in vertical alignment and compatibility and to provide a liquid crystal display device produced using the same. The problem is solved by a liquid crystal composition containing one or two or more kinds of self-aligning polymerizable monomers and one or two or more kinds of polymerizable monomers (or polymerizable compounds) having a specific chemical structure, and a liquid crystal display device produced using the same, specifically a liquid crystal composition containing a polymerizable monomer represented by General Formula (I) and a spontaneously aligning monomer which has a chemical structure different from that of the polymerizable monomer represented by General Formula (I), and has a polar group, and a liquid crystal display device containing the same.

Claims (61)

1. A liquid crystal composition for a liquid crystal display device, the liquid crystal composition comprising:

a polymerizable monomer represented by General Formula (I); and

a spontaneously aligning monomer selected from the group consisting of compounds represented by Formulae (P-1-1) to (P-1-15), (P-1-20) to (P-1-26), (P-J-10) to (P-J-50), and (P-1) to (P-18),

wherein the content of the polymerizable monomer represented by General Formula (I) is 0.02 to 2.5% by mass, and the content of the spontaneously aligning monomer is 0.02 to 2.5% by mass,

wherein R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 , R 108 , R 109 , and R 110 each independently represent any selected from the group consisting of P 11 —S 11 —, an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a halogen atom, and a hydrogen atom, and P 11 represents any of the following Formula (R-I) to Formula (R-IX):

wherein

R 21 , R 31 , R 41 , R 51 , and R 61 are each independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms,

W is a single bond, —O—, or a methylene group,

T is a single bond or —COO—,

p, t, and q are each independently 0, 1, or 2,

S 11 represents a single bond or an alkylene group having 1 to 15 carbon atoms, and one or two or more —CH 2 —'s in the alkylene group may be substituted with —O—, —OCO—, or —COO— so that an oxygen atom is not directly adjacent thereto,

n 11 represents 0, 1, or 2,

A 11 represents a group selected from the group consisting of a group (a), a group (b), and a group (c) as follows:

(a) 1,4-cyclohexylene group (one —CH 2 — or two or more non-adjacent —CH 2 —'s present in this group may be substituted with —O—),

(b) 1,4-phenylene group (one —CH═ or two or more non-adjacent —CH═'s present in this group may be substituted with —N═), and

(c) naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or decahydronaphthalene-2,6-diyl group (one —CH═ or two or more non-adjacent —CH═'s present in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be substituted with —N═),

the group (a), the group (b), and the group (c) may be each independently substituted with an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, halogen atoms, a cyano group, a nitro group, or P 11 —S 11 —,

L 10 and L 11 each independently represent a single bond, —OCH 2 —, —CH 2 O—, —C 2 H 4 —, —OC 2 H 4 O—, —COO—, —OCO—, —CH═CR a —COO—, —CH═CR a —OCO—, —COO—CR a ═CH—, —OCO—CR a ═CH—, —(CH 2 ) z —COO—, —(CH 2 ) z —OCO—, —OCO—(CH 2 ) z —, —COO—(CH 2 ) z —, —CH═CH—, —CF 2 O—, —OCF 2 —, or —C≡C— (wherein, R a 's each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and z's each independently represent an integer of 1 to 4),

at least two or more P 11 —S 11 —'s are included in one molecule of General Formula (I), and

at least one alkyl group having 1 to 18 carbon atoms is included in the polymerizable monomer represented by General Formula (I), in which one —CH 2 — or two or more non-adjacent —CH 2 —'s in an alkylene group of said at least one alkyl group may be each independently substituted with —O—, and

in a case where there are a plurality of P 11 's, S 11 's, L 11 's, and A 11 's, those may be the same as or different from each other,

2. The liquid crystal composition according to claim 1 , wherein

in General Formula (I), n 11 is 0 or 1.

3. The liquid crystal composition according to claim 1 , wherein

in General Formula (I), L 10 and L 11 are single bonds.

4. The liquid crystal composition according to claim 1 , further comprising:

one or two or more kinds of compounds selected from the group consisting of compounds represented by General Formulae (N-1), (N-2), and (N-3):

wherein

R N11 , R N12 , R N21 , R N22 , R N31 , and R N32 each independently represent an alkyl group having 1 to 8 carbon atoms, and one —CH 2 — or two or more non-adjacent —CH 2 —'s in the alkyl group may be each independently substituted with —CH═CH—, —C≡C—, —O—, —CO—, —COO—, or —OCO—,

A N11 , A N12 , A N21 , A N22 , A N31 , and A N32 each independently represent a group selected from the group consisting of

(a) 1,4-cyclohexylene group (one —CH 2 — or two or more non-adjacent —CH 2 —'s present in this group may be substituted with —O—),

(b) 1,4-phenylene group (one —CH═ or two or more non-adjacent —CH═'s present in this group may be substituted with —N═),

(c) naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or decahydronaphthalene-2,6-diyl group (one —CH═ or two or more non-adjacent —CH═'s present in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be substituted with —N═), and

(d) 1,4-cyclohexenylene group,

the group (a), the group (b), the group (c), and the group (d) may be each independently substituted with a cyano group, a fluorine atom, or a chlorine atom,

Z N11 , Z N12 , Z N21 , Z N22 , Z N31 , and Z N32 each independently represent a single bond, —CH 2 CH 2 —, —(CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —OCF 2 —, —CF 2 O—, —CH═N—N═CH—, —CH═CH—, —CF═CF—, or —C≡C—,

X N21 represents a hydrogen atom or a fluorine atom,

T N31 represents a —CH 2 — or an oxygen atom, and

n N11 , n N12 , n N21 , n N22 , n N31 , and n N32 each independently represent an integer of 0 to 3, wherein n N11 +n N12 , n N21 +n N22 , and n N31 +n N32 each independently represent 1, 2, or 3, and in a case where there are a plurality of A N11 's to A N32 's and Z N11 's to Z N32 's, those may be the same as or different from each other.

5. The liquid crystal composition according to claim 1 , further comprising:

one or two or more kinds of compounds selected from compounds represented by General Formula (L):

wherein

R L1 and R L2 each independently represent an alkyl group having 1 to 8 carbon atoms, wherein one —CH 2 — or two or more non-adjacent —CH 2 —'s in the alkyl group may be each independently substituted with —CH═CH—, —C≡C—, —O—, —CO—, —COO—, or —OCO—,

n L1 represents 0, 1, 2, or 3,

A L1 , A L2 , and A L3 each independently represent a group selected from the group consisting of

(a) 1,4-cyclohexylene group (one —CH 2 — or two or more non-adjacent —CH 2 —'s present in this group may be substituted with —O—),

(b) 1,4-phenylene group (one —CH═ or two or more non-adjacent —CH═'s present in this group may be substituted with —N═), and

(c) naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or decahydronaphthalene-2,6-diyl group (one —CH═ or two or more non-adjacent —CH═'s present in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be substituted with —N═),

the group (a), the group (b), and the group (c) may be each independently substituted with a cyano group, a fluorine atom, or a chlorine atom,

Z L1 and Z L2 each independently represent a single bond, —CH 2 CH 2 —, —(CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —OCF 2 —, —CF 2 O—, —CH═N—N═CH—, —CH═CH—, —CF═CF—, or —C≡C—,

in a case where n L1 is 2 or 3 and a plurality of A L2 's are present, those may be the same as or different from each other, and in a case where n L1 is 2 or 3 and a plurality of Z L2 's are present, those may be the same as or different from each other.

6. The liquid crystal composition according to claim 1 for use in a liquid crystal display device having a pair of substrates, at least one of which is provided with no alignment film on a surface.

7. A liquid crystal display device comprising the liquid crystal composition according to claim 1 .

8. A liquid crystal display device for active matrix drive comprising the liquid crystal composition according to claim 1 .

9. A liquid crystal display device for a PSA mode, a PSVA mode, a PS-IPS mode, or a PS-FFS mode comprising the liquid crystal composition according to claim 1 .

10. A liquid crystal display device having a pair of substrates, at least one of which is provided with no alignment film on a surface, the device comprising:

a first substrate and a second substrate which are disposed opposite to each other;

a liquid crystal layer which is placed between the first substrate and the second substrate;

an electrode layer which has a plurality of gate bus lines and data bus lines arranged in a matrix, a thin film transistor provided at each intersection of the gate bus lines and the data bus lines, and a pixel electrode driven by the thin film transistor for each pixel, on the first substrate;

a common electrode which is formed on the first substrate or the second substrate; and

a resin component formed by curing the polymerizable monomer and the spontaneously aligning monomer of the liquid crystal composition according to claim 1 between the first substrate and the second substrate.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 24, 2024
From: DIC CORPORATION
To: SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIAL CO., LTD.
Reel/Frame 067528/0688 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2019
From: MAMIYA, JUNICHI; INOUE, YUICHI; KIMURA, MASAOMI; YAMAMOTO, JUNKO; HAYASHI, MASANAO; SUGIYAMA, HIROKAZU
To: DIC CORPORATION
Reel/Frame 050951/0640 →
Priority Claims (2)
JP JP2017-109172 · Jun 1, 2017 · national
JP JP2018-013593 · Jan 30, 2018 · national
Continuity (1)
Related Publication 20200224098A1 · Jul 16, 2020