IP Library Granted Patent US 9,181,478
Granted Patent B2
US 9,181,478 · App. 14/389,215 · Granted Nov 10, 2015

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
C09K19/12C09K19/20C09K19/3003G02F1/13C09K2019/0466C09K2019/122C09K2019/123C09K2019/3004C09K2019/3016C09K2019/3019C09K2019/3027
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Quick Facts
Patent No.
US 9,181,478
App. No.
14/389,215
Granted
Nov 10, 2015
Kind
B2
Abstract

A composition contains three or more compounds represented by general formula (i) below. (In the formula, R i1 represents an alkyl group having 1 to 8 carbon atoms, and one or nonadjacent two or more —CH 2 — in the alkyl group may be each independently substituted by —CH═CH—, —C≡C—, —O—, —CO—, —COO—, or —OCO—; m i1 represents 1 or 2; A i1 represents a 1,4-cyclohexylene group or a 1,4-phenylene group which may have a fluorine atom or a chlorine atom substituted for a hydrogen atom, when m i1 represents 1, A i1 represents a 1,4-phenylene group which may have a fluorine atom or a chlorine atom substituted for a hydrogen atom, and when m i1 represents 2 and a plurality of A i1 are present, A i1 may be the same or different, and X i1 represents a hydrogen atom, a fluorine atom, or a chlorine atom.)

Claims (36)

1. A liquid crystal composition comprising three or more compounds represented by general formula (i) below, at least one compound represented by general formula (i′-2) below being contained as a compound represented by general formula (i) below, and further comprising at least one compound selected from the group consisting of a compound represented by general formula (I-1-1) below, a compound represented by general formula (I-1-2) below, a compound represented by general formula (IV-1) below, a compound represented by general formula (III) below, a compound represented by general formula (X-4) below, a compound represented by general formula (IX-1) below, a compound represented by general formula (XI-1) below, and a compound represented by general formula (VIII-1) below:

(In the formula, R i1 represents an alkyl group having 1 to 8 carbon atoms, and one or nonadjacent two or more —CH 2 — in the alkyl group may be each independently substituted by —CH═CH—, —C≡C—, —O—, —CO—, —COO—, or —OCO—; m i1 represents 1 or 2; A i1 represents a 1,4-cyclohexylene group or a 1,4-phenylene group which may have a fluorine atom or a chlorine atom substituted for a hydrogen atom, when m i1 represents 1, A i1 represents a 1,4-phenylene group which may have a fluorine atom or a chlorine atom substituted for a hydrogen atom, and when m i1 represents 2 and a plurality of A i1 are present, A i1 may be the same or different; and X i1 represents a hydrogen atom, a fluorine atom, or a chlorine atom)

(In the formula, R i1 represents the same meaning as R i1 in the general formula (i), and X i1 represents a fluorine atom)

(In the formulae, R 12 each independently represent 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 5 carbon atoms)

(In the formula, R 43 and R 44 each independently represent an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms)

(In the formula, R 31 and R 32 each independently represent an alkenyl group having 2 to 5 carbon atoms, an alkyl group having 1 to 5 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms)

(In the formula, X 102 represents a fluorine atom or a hydrogen atom, and R 10 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)

(In the formula, 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, X 92 represents a hydrogen atom or a fluorine atom, and Y 9 represents a fluorine atom or —OCF 3 )

(In the formula, R 11 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)

(In the formula, 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).

2. The liquid crystal composition according to claim 1 , comprising at least one compound represented by general formula (i-2) below and at least one compound represented by general formula (i-1) below as the compounds represented by the general formula (i):

(In the formula (i-1), R i1 represents the same meaning as R i1 in the general formula (i), and X i1 represents the same meaning X i1 as in the general formula (i), and in the formula (i-2), X i1 represents the same meaning as R i1 in the general formula (i), and X i1 represents a hydrogen atom or a chlorine atom).

3. The liquid crystal composition according to claim 2 , comprising at least two compounds represented by general formula (i-2) as the compounds represented by the general formula (i).

4. The liquid crystal composition according to claim 1 , further comprising a compound represented by general formula (L) below:

[Chem. 12]

R L1 —B L1 -L L1 -B L2 L L2 -B L3 OL R L2   (L)

(In the formula, R L1 and R L2 each independently represents an alkyl group having 1 to 8 carbon atoms, and one or nonadjacent two or more —CH 2 — in the alkyl group may be each independently substituted by —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 (one —CH 2 — or nonadjacent two or more —CH 2 — present in the group may be substituted by —O—); and

(b) a 1,4-phenylene group (one —CH═ or nonadjacent two or more —CH═ present in the group may be substituted by —N═), and the group (a) and the group (b) may be each independently substituted by a cyano group, a fluorine atom, or a chlorine 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—, —CF═CF—, or —C≡C—; and

when OL is 2 or 3 and a plurality of L L2 are present, L L2 may be the same or different, and when OL is 2 or 3 and a plurality of B L3 are present, B L3 may be the same or different, the compound represented by the general formula (I-1-1), the compound represented by the general formula (I-1-2), the compound represented by the general formula (IV-1), and the compound represented by the general formula (III) being excluded).

5. The liquid crystal composition according to claim 1 , further comprising a compound represented by general formula (M) below:

(In the formula, R M1 represents an alkyl group having 1 to 8 carbon atoms, and one or nonadjacent two or more —CH 2 — in the alkyl group may be each independently substituted by —CH═CH—, —C≡C—, —O—, —CO—, —COO—, or —OCO—;

PM represents 0, 1, 2, 3, or 4;

C M1 and C M2 each independently represent a group selected from the group consisting of:

(d) a 1,4-cyclohexylene group (one —CH 2 — or nonadjacent two or more —CH 2 — present in the group may be substituted by —O— or —S—); and

(e) a 1,4-phenylene group (one —CH═ or nonadjacent two or more —CH═ present in the group may be substituted by —N═), and the group (d) and the group (e) may be each independently substituted by a cyano group, a fluorine atom, or a chlorine 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—;

when PM is 2, 3, or 4 and a plurality of K M1 are present, K M1 may be the same or different, and when PM is 2, 3, or 4 and a plurality of C M2 are present, C M2 may be the same or different;

X M1 and X M3 each independently represent a hydrogen atom, a chlorine atom, or a fluorine atom; and

X M2 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, or a 2,2,2-trifluoroethyl group, the compound represented by the general formula (i), the compound represented by the general formula (X-4), the compound represented by the general formula (IX-1), the compound represented by the general formula (XI-1), and the compound represented by the general formula (VIII-1) being excluded).

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

7. An IPS device comprising the liquid crystal composition according to claim 1 .

8. A FFS device comprising the liquid crystal composition 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 Sep 29, 2014
From: KAWAMURA, JOJI; NEGISHI, MAKOTO; NIWA, MASAHIRO
To: DIC CORPORATION
Reel/Frame 033843/0296 →
Continuity (1)
Related Publication 20150053891A1 · Feb 26, 2015