IP Library Granted Patent US 9,296,949
Granted Patent B2
US 9,296,949 · App. 13/822,971 · Granted Mar 29, 2016

Nematic liquid crystal composition and liquid crystal display element using the same

Inventors: Takeshi Kuriyama (Kitaadachi-gun, JP); Joji Kawamura (Kitaadachi-gun, JP)
Assignee: DIC CORPORATION
C09K19/3003C09K19/0403C09K19/062C09K19/20C09K19/3066C09K19/44C09K19/54C09K2019/0448C09K2019/0466C09K2019/123C09K2019/301C09K2019/3004C09K2019/3009C09K2019/3016C09K2019/3019C09K2019/3021C09K2019/3422C09K2019/548
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Quick Facts
Patent No.
US 9,296,949
App. No.
13/822,971
Granted
Mar 29, 2016
Kind
B2
Abstract

The nematic liquid crystal composition exhibits a positive dielectric anisotropy (Δ∈), the liquid crystal composition being useful as a liquid crystal display material, and a liquid crystal display element using the same. The liquid crystal composition of the present invention has a large absolute value of dielectric anisotropy thereof and a low viscosity. By using this liquid crystal composition, it is possible to provide a liquid crystal display element which has a high contrast, high-speed responsiveness, and good display quality in which image sticking and display defects are not generated. The liquid crystal display element using the liquid crystal composition is a useful display element which realizes both high-speed response and suppression of display defects. In particular, the liquid crystal display element is useful as a liquid crystal display element for active-matrix driving, and can be applied to, for example, an IPS-type or TN-type liquid crystal display element.

Claims (51)

1. A nematic liquid crystal composition comprising:

as a first component, at least one compound represented by general formula (I):

where R 1 represents a linear or branched alkyl group having 1 to 22 carbon atoms and one CH 2 group in the alkyl group may be substituted with —O—; and M 1 represents a trans-1,4-cyclohexylene group; and

as a second component, at least one compound selected from the group consisting of compounds represented by general formulae (II-a) to (II-e):

where R 21 to R 30 each independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms and X 21 represents a hydrogen atom or a fluorine atom, wherein a dielectric anisotropy (Δ∈) at 25° C. is +3.5 or more.

2. The nematic liquid crystal composition according to claim 1 , further comprising, as a third component, at least one compound represented by general formula (III):

where R 31 represents an alkyl group or alkoxy group having 1 to 10 carbon atoms, or an alkenyl group or alkenyloxy group having 2 to 10 carbon atoms; M 31 to M 33 each independently represent a trans-1,4-cyclohexylene group or a 1,4-phenylene group, one or two —CH2- groups in the trans-1,4-cyclohexylene group may be substituted with —O— so that oxygen atoms are not directly adjacent to each other, and one or two hydrogen atoms in the phenylene group may be substituted with a fluorine atom; X 31 and X 32 each independently represent a hydrogen atom or a fluorine atom; Z 31 represents a fluorine atom, a trifluoromethoxy group, or a trifluoromethyl group; n 31 and n 32 each independently represent 0, 1, or 2; n 31 +n 32 represents 0, 1, or 2; and when plural M 31 s and M 33 s are present, they may be the same or different.

3. The nematic liquid crystal composition according to claim 2 , wherein general formula (III) is represented by any one of general formulae (III-a) to (III-e):

where R 32 represents an alkyl group or alkoxy group having 1 to 10 carbon atoms, or an alkenyl group or alkenyloxy group having 2 to 10 carbon atoms; X 31 to X 38 each independently represent a hydrogen atom or a fluorine atom; and Z 31 represents a fluorine atom, a trifluoromethoxy group, or a trifluoromethyl group.

4. The nematic liquid crystal composition according to claim 3 , further comprising at least one compound selected from the group consisting of compounds represented by general formulae (IV-a) to (IV-f):

where R 41 represents an alkyl group or alkoxy group having 1 to 10 carbon atoms, or an alkenyl group or alkenyloxy group having 2 to 10 carbon atoms; X 41 to X 48 each independently represent a hydrogen atom or a fluorine atom; and Z 41 represents a fluorine atom, a trifluoromethoxy group, or a trifluoromethyl group.

5. The nematic liquid crystal composition according to claim 4 , wherein, in general formula (I), R 1 represents a linear or branched alkyl group having 1 to 10 carbon atoms.

6. The nematic liquid crystal composition according to claim 5 , wherein the content of the at least one compound represented by general formula (I) is 0.001% to 1% by mass, and the content of the at least one compound represented by general formula (II) is 10% to 70% by mass.

7. The nematic liquid crystal composition according to claim 6 , further comprising a polymerizable compound represented by general formula (V):

where X 51 and X 52 each independently represent a hydrogen atom or a methyl group;

Sp 1 and Sp 2 each independently represent a single bond, an alkylene group having 1 to 8 carbon atoms, or —O—(CH 2 ) s —

where s represents an integer of 2 to 7 and the oxygen atom is bonded to an aromatic ring;

Z 51 represents —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CY 1 ═CY 2 — (where Y 1 and Y 2 each independently represent a fluorine atom or a hydrogen atom), —C≡C—, or a single bond; and

M 51 represents a 1,4-phenylene group, a trans-1,4-cyclohexylene group, or a single bond, and any hydrogen atom in all the 1,4-phenylene groups in the formula may be substituted with a fluorine atom.

8. A liquid crystal display element for active-matrix driving, the liquid crystal display element comprising the liquid crystal composition according to claim 7 .

9. A liquid crystal display element for an IPS mode, an FFS mode, or a VA-IPS mode, the liquid crystal display element comprising the liquid crystal composition according to claim 7 .

10. A polymer-stabilized mode liquid crystal display element produced by using the nematic liquid crystal composition according to claim 7 , the liquid crystal composition containing a polymerizable compound, and polymerizing the polymerizable compound contained in the liquid crystal composition with or without application of a voltage.

11. The nematic liquid crystal composition according to claim 1 , wherein the first component further comprises a compound represented by the formula (1-b):

wherein R 12 is a linear alkyl group or branched alkyl group having 1 to 20 carbon atoms, and L 1 is a linear alkylene group or branched alkylene group having 1 to 8 carbon atoms.

12. The nematic liquid crystal composition according to claim 1 , wherein the first component is represented by the formula (1-c):

wherein R 13 is a linear alkyl group, branched alkyl group, linear alkoxy group, or branched alkoxy group having 1 to 8 carbon atoms.

13. The nematic liquid crystal composition according to claim 1 , wherein the first component is represented by the formula (1-c-1)

14. A nematic liquid crystal composition comprising:

as a first component, at least one compound represented by general formula (I):

where R 1 represents a linear or branched alkyl group having 1 to 22 carbon atoms and one CH 2 group in the alkyl group may be substituted with —O—; and M 1 represents a trans-1,4-cyclohexylene group;

as a second component, at least one compound selected from the group consisting of compounds represented by general formulae (II-a) to (II-e):

where R 21 to R 30 each independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms and X 21 represents a hydrogen atom or a fluorine atom, wherein a dielectric anisotropy (Δ∈) at 25° C. is +3.5 or more, and

a third component, at least one compound represented by general formula (III):

where R 31 represents an alkyl group or alkoxy group having 1 to 10 carbon atoms, or an alkenyl group or alkenyloxy group having 2 to 10 carbon atoms; M 31 to M 33 each independently represent a trans-1,4-cyclohexylene group or a 1,4-phenylene group, one or two —CH2- groups in the trans-1,4-cyclohexylene group may be substituted with —O— so that oxygen atoms are not directly adjacent to each other, and one or two hydrogen atoms in the phenylene group may be substituted with a fluorine atom; X 31 and X 32 each represent a fluorine atom; Z 31 represents a fluorine atom; n 31 and n 32 each independently represent 0, 1, or 2; n 31 +n 32 represents 0, 1, or 2; and when plural M 31 s and M 33 s are present, they may be the same or different.

15. The nematic liquid crystal composition according to claim 14 , wherein general formula (III) is represented by any one of general formulae (III-a) to (III-e):

where R 32 represents an alkyl group or alkoxy group having 1 to 10 carbon atoms, or an alkenyl group or alkenyloxy group having 2 to 10 carbon atoms; X 31 to X 32 each represent a fluorine atom, X 33 to X 38 each independently represent a hydrogen atom or a fluorine atom; and Z 31 represents a fluorine atom, a trifluoromethoxy group, or a trifluoromethyl group.

16. The nematic liquid crystal composition according to claim 15 , further comprising at least one compound selected from the group consisting of compounds represented by general formulae (IV-a) to (IV-f):

where R 41 represents an alkyl group or alkoxy group having 1 to 10 carbon atoms, or an alkenyl group or alkenyloxy group having 2 to 10 carbon atoms; X 41 to X 48 each independently represent a hydrogen atom or a fluorine atom; and Z 41 represents a fluorine atom, a trifluoromethoxy group, or a trifluoromethyl group.

17. The nematic liquid crystal composition according to claim 16 , further comprising a polymerizable compound represented by general formula (V):

where X 51 and X 52 each independently represent a hydrogen atom or a methyl group;

Sp 1 and Sp 2 each independently represent a single bond, an alkylene group having 1 to 8 carbon atoms, or —O—(CH 2 ) s —

where s represents an integer of 2 to 7 and the oxygen atom is bonded to an aromatic ring;

Z 51 represents —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CY 1 ═CY 2 — (where Y 1 and Y 2 each independently represent a fluorine atom or a hydrogen atom), —C≡C—, or a single bond; and

M 51 represents a 1,4-phenylene group, a trans-1,4-cyclohexylene group, or a single bond, and any hydrogen atom in all the 1,4-phenylene groups in the formula may be substituted with a fluorine atom.

18. A polymer-stabilized mode liquid crystal display element produced by using the nematic liquid crystal composition according to claim 17 , the liquid crystal composition containing a polymerizable compound, and polymerizing the polymerizable compound contained in the liquid crystal composition with or without application of a voltage.

19. The nematic liquid crystal composition according to claim 14 , wherein the first component further comprises a compound represented by the formula (1-b):

wherein R 12 is a linear alkyl group or branched alkyl group having 1 to 20 carbon atoms, and L 1 is a linear alkylene group or branched alkylene group having 1 to 8 carbon atoms.

20. The nematic liquid crystal composition according to claim 14 , wherein the second component comprises a compound represented by general formula (II-a)

and

wherein the third component comprises at least one compound selected from the group consisting of compounds represented by general formulae (III-b), (III-d) and (III-e)

where R 21 to R 22 each independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, R 32 represents an alkyl group or alkoxy group having 1 to 10 carbon atoms, or an alkenyl group or alkenyloxy group having 2 to 10 carbon atoms; X 31 to X 32 each represent a fluorine atom, X 33 to X 38 each independently represent a hydrogen atom or a fluorine atom; and Z 31 represents a fluorine atom.

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 Jul 19, 2013
From: KURIYAMA, TAKESHI; KAWAMURA, JOJI
To: DIC CORPORATION
Reel/Frame 030840/0865 →
Priority Claims (1)
JP 2012-117546 · May 23, 2012 · national
Continuity (1)
Related Publication 20150060733A1 · Mar 5, 2015