IP Library Granted Patent US 9,441,160
Granted Patent B2
US 9,441,160 · App. 14/416,930 · Granted Sep 13, 2016

Fluorobiphenyl-containing composition

Inventors: Joji Kawamura (Kita-adachi-gun, JP); Makoto Negishi (Kita-adachi-gun, JP); Masahiro Niwa (Kita-adachi-gun, JP)
Assignee: DIC CORPORATION
C09K19/3066C09K19/062C09K19/063C09K2019/0448C09K2019/0466C09K2019/122C09K2019/123C09K2019/124C09K2019/301C09K2019/3004C09K2019/3006C09K2019/3009C09K2019/3016C09K2019/3019C09K2019/3021C09K2019/3071C09K2019/3077C09K2019/3078G02F1/13394G02F1/133377
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Quick Facts
Patent No.
US 9,441,160
App. No.
14/416,930
Granted
Sep 13, 2016
Kind
B2
Abstract

There is provided a composition containing a compound represented by General Formula (i) and a compound represented by General Formula (ii) (where R i1 , R ii1 , and R ii2 each independently represent an alkyl group having 1 to 8 carbon atoms; in the alkyl group, one —CH 2 — group or two or more —CH 2 — groups not adjoining each other are each independently optionally substituted with —CH═CH—, —C≡C—, —O—, —CO—, —COO—, or —OCO—; m i1 represents 2; A i1 represents a 1,4-cyclohexylene group or a 1,4-phenylene group of which a hydrogen atom is optionally substituted with a fluorine atom or a chlorine atom; multiple A i1 's may be the same as or different from each other; Z i1 represents a single bond, —CH═CH—, —C≡C—, —CH 2 CH 2 —, —COO—, or —OCO—; multiple Z i1 's may be the same as or different from each other; and X i1 and X ii1 to X ii4 each independently represent a hydrogen atom or a fluorine atom).

Claims (36)

1. A composition used in a liquid crystal display device, the composition consisting of:

a compound represented by General Formula (i);

a compound represented by General Formula (ii);

a compound represented by General Formula (VIII-1);

a compound represented by General Formula (I-1-1);

a compound represented by General Formula (I-1-2),

a compound represented by General Formula (L);

a compound represented by General Formula (M);

optionally a compound represented by General Formula (Q); and

optionally a polymerizable compound;

wherein the total amount of the compound represented by General Formula (I-1-1) and the compound represented by General Formula (I-1-2) is at least 31 mass % relative to the total amount of the composition, and the amount of the compound represented by General Formula (VIII-1) is in the range of 2 mass % to 8 mass % relative to the total amount of the composition,

where R i1 , R ii1 , and R ii2 each independently represent an alkyl group having 1 to 8 carbon atoms; in the alkyl group, one —CH 2 — group or two or more —CH 2 — groups not adjoining each other are each independently optionally substituted with —CH═CH—, —C≡C—, —O—, —CO—, —COO—, or —OCO—; m i1 represents 2; A i1 represents a 1,4-cyclohexylene group; Z i1 represents a single bond; and X i1 and X ii1 to X ii4 each independently represent a hydrogen atom or a fluorine atom,

where R 8 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms,

where R 12 's each independently represent an alkyl group having 1 to 5 carbon atoms

where R L1 and R L2 each independently represent a linear alkyl group having 1 to 8 carbon atoms, and one —CH 2 — group or two or more —CH 2 — groups not adjoining each other in the alkyl group are each independently optionally substituted with —CH═CH—, —C≡C—, —O—, —CO—, —COO—, or —OCO—; OL represents 0, 1, 2, or 3; B L1 , B L2 , and B L3 each independently represent a group selected from the group consisting of

(a) a 1,4-cyclohexylene group in which one —CH 2 — group or two or more —CH 2 — groups not adjoining each other are optionally substituted with —O—, and

(b) a 1,4-phenylene group in which one —CH═ group or two or more —CH═ groups not adjoining each other are optionally substituted with —N═, and

the groups (a) and (b) are each independently optionally substituted with a cyano group, or a fluorine atom; L L1 and L 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—, or —C≡C—; in the case where OL is 2 or 3 and where L L2 is multiple, the multiple L L2 's are the same as or different from each other; in the case where OL is 2 or 3 and where B L3 is multiple, the multiple B L3 's are the same as or different from each other; wherein the compound represented by General Formula (L) excludes the compound represented by General Formula (ii), the compound represented by General Formula (I-1-1), and the compound represented by General Formula (I-1-2),

where R M1 represents an alkyl group having 1 to 8 carbon atoms, and one —CH 2 — group or two or more —CH 2 — groups not adjoining each other in the alkyl group are each independently optionally substituted with —CH═CH—, —C≡C—, —O—, —CO—, —COO—, or —OCO—; PM represents 0, 1, or 2; C M1 and C M2 each independently represent a group selected from the group consisting of

(d) a 1,4-cyclohexylene group in which one —CH 2 — group or two or more —CH 2 — groups not adjoining each other are optionally substituted with —O— or —S—, and

(e) a 1,4-phenylene group in which one —CH═ group or two or more —CH═ groups not adjoining each other are optionally substituted with —N═, and

the groups (d) and (e) are each independently optionally substituted with a cyano group, or a fluorine atom; K M1 and K M2 each independently represent a single bond, —CH 2 CH 2 —, —(CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 O—, —COO—, —OCO—, or —C≡C—; in the case where PM is 2 and where K M1 is multiple, the multiple K M1 's are the same as or different from each other; in the case where PM is 2 and where C M2 is multiple, the multiple C M2 's are the same as or different from each other; X M1 and X M3 each independently represent a hydrogen atom, or a fluorine atom; X M2 represents a hydrogen atom, a fluorine atom, a cyano group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, or a 2,2,2-trifluoroethyl group; and the compound represented by General Formula (M) excludes the compound represented by General Formula (i) and the compound represented by General Formula (VIII-1),

where R Q represents a linear or branched alkyl group having 1 to 22 carbon atoms; at least one CH 2 group in the alkyl group is optionally substituted with —O—, —CH═CH—, —CO—, —OCO—, —COO—, —C≡C—, —CF 2 O—, or —OCF 2 — such that oxygen atoms do not directly adjoin each other; and M Q represents a trans-1,4-cyclohexylene group, a 1,4-phenylene group, or a single bond.

2. The composition used in a liquid crystal display device according to claim 1 , wherein in the compound represented by General Formula (ii), X ii2 is a fluorine atom; and X ii1 , X ii3 , and X ii4 are hydrogen atoms.

3. The composition used in a liquid crystal display device according to claim 1 , wherein the compound represented by General Formula (M) is a compound represented by General Formula (XIII-3)

where R 13 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

4. The composition used in a liquid crystal display device according to claim 1 , wherein the compound represented by General Formula (M) comprises at least two compounds represented by General Formula (IX-2-5)

where R 9 represents an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

5. The composition used in a liquid crystal display device according to claim 1 , wherein the compound represented by General Formula (L) comprises at least three compounds represented by General Formula (IV-1)

where R 43 and R 44 each independently represent an alkyl group having 1 to 5 carbon atoms.

6. The composition used in a liquid crystal display device according to claim 1 , wherein at least three compounds represented by General Formula (I-1-2) are used

where R 12 each independently represent an alkyl group having 1 to 5 carbon atoms.

7. The composition used in a liquid crystal display device according to claim 1 , wherein at least one of X ii1 to X ii4 is a fluorine atom.

8. A liquid crystal display device comprising the composition used in a liquid crystal display device according to claim 1 .

9. An IPS device comprising the composition used in a liquid crystal display device according to claim 1 .

10. An FFS device comprising the composition used in a liquid crystal display device according to claim 1 .

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 Jan 23, 2015
From: KAWAMURA, JOJI; NEGISHI, MAKOTO; NIWA, MASAHIRO
To: DIC CORPORATION
Reel/Frame 034802/0372 →
Continuity (1)
Related Publication 20150291881A1 · Oct 15, 2015