# US 9,434,883 B2 · Liquid crystal composition and liquid crystal display device

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- Number: US 9,434,883 B2
- Document ID: US9434883B2
- Status: Granted
- Kind: B2
- Application number: 14/806,657
- Filed: 2015-07-23
- Published: 2016-02-04
- Granted: 2016-09-06
- Earliest claimed: 2014-07-29
- Assignees: Jnc Corporation; Jnc Petrochemical Corporation
- Applicants: Jnc Corporation; Jnc Petrochemical Corporation
- Inventors: Yoshimasa Furusato; Masayuki Saito
- Web page: https://patentgrep.com/patent/US9434883B2

## CPC

- C09K 19/54: Additives having no specific mesophase {characterised by their chemical composition}
- C09K 19/0208: {Twisted Nematic (T.N.); Super Twisted Nematic (S.T.N.); Optical Mode Interference (O.M.I.)}
- C09K 19/20: linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters {or ethers}
- C09K 19/3066: {in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers}
- C09K 19/3402: {having oxygen as hetero atom (sugars C09K19/0422)}
- C09K 2019/0466: {the linking chain being a -CF2O- chain}
- C09K 2019/123: {Ph-Ph-Ph}
- C09K 2019/301: {Cy-Cy-Ph}
- C09K 2019/3021: {Cy-Ph-Ph-Cy}
- C09K 2019/3025: {Cy-Ph-Ph-Ph}
- C09K 2019/3071: {Cy-Cy-COO-Cy}
- C09K 2019/3077: {Cy-Cy-COO-Ph}
- C09K 2019/3078: {Cy-Cy-COO-Ph-Cy}
- C09K 2019/3083: {Cy-Ph-COO-Ph}
- C09K 2019/3422: {the heterocyclic ring being a six-membered ring}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

A liquid crystal composition having at least one or a suitable balance regarding at least two of characteristic such as high maximum temperature of a nematic phase, low minimum temperature thereof, small viscosity, suitable optical anisotropy, large dielectric anisotropy, large specific resistance, high stability to ultraviolet-light or heat, or large elastic constant; an AM-device having short response time, a large voltage holding ratio, low threshold voltage, a large contrast ratio, a negatively large DC brightness relaxation time constant and long-service-life. The liquid crystal composition contains a compound contributing to high stability to heat or ultraviolet-light as an additive component and a specific compound having positively large dielectric anisotropy, and a liquid crystal display device includes the composition. The composition may contain a specific compound having high maximum temperature or small viscosity as a second component or a specific compound having negative dielectric anisotropy as a third component.

## Claims

### Claim 1

A liquid crystal composition that has a positive dielectric anisotropy and a nematic phase, and contains at least one compound selected from the group of compounds represented by formula (1) as an additive component and at least one compound from the group of compounds represented by formula (2) as a first component:
wherein, in formula (1), R1 is hydrogen or alkyl having 1 to 15 carbons; R2, R3, R4 and R5 are independently hydrogen or alkyl having 1 to 4 carbons; ring A is a polyvalent group derived from benzene or cyclohexane by eliminating hydrogen; a is 3 or 4; and
in formula (2), R6 is alkyl having 1 to 12 carbons, alkoxy having to 12 carbons or alkenyl having 2 to 12 carbons; ring B is 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl or tetrahydropyran-2,5-diyl; Z1 is a single bond, ethylene, carbonyloxy or difluoromethyleneoxy; X1 and X2 are independently hydrogen or fluorine; Y1 is fluorine, chlorine, alkyl having 1 to 12 carbons in which at least one of hydrogen is replaced by fluorine or chlorine, alkoxy having 1 to 12 carbons in which at least one of hydrogen is replaced by fluorine or chlorine, or alkenyloxy having 2 to 12 carbons in which at least one of hydrogen is replaced by fluorine or chlorine; and b is 1, 2, 3 or 4.

### Claim 2 (depends on 1)

The liquid crystal composition according to claim 1, containing a compound represented by formula (1-1) or formula (1-2) as the additive component:

### Claim 3 (depends on 1)

The liquid crystal composition according to claim 1, wherein a ratio of the additive component is in the range of 0.005% by weight to 1% by weight based on the weight of the liquid crystal composition.

### Claim 4 (depends on 1)

The liquid crystal composition according to claim 1, containing at least one compound selected from the group of compounds represented by formula (2-1) to (2-35) as the first component:
wherein, in formula (2-1) to (2-35), R6 is alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkenyl having 2 to 12 carbons.

### Claim 5 (depends on 1)

The liquid crystal composition according to claim 1, wherein a ratio of the first component is in the range of 10% by weight to 90% by weight based on the weight of the liquid crystal composition.

### Claim 6 (depends on 1)

The liquid crystal composition according to claim 1, containing at least one compound selected from the group of compounds represented by formula (3) as a second component:
wherein, in formula (3), R7 and R8 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkyl having 1 to 12 carbons in which at least one of hydrogen is replaced by fluorine or chlorine, or alkenyl having 2 to 12 carbons in which at least one of hydrogen is the replaced by fluorine or chlorine; ring C and ring D are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene; Z2 is a single bond, ethylene or carbonyloxy; and c is 1, 2 or 3.

### Claim 7 (depends on 6)

The liquid crystal composition according to claim 6, containing at least one compound selected from the group of compounds represented by formula (3-1) to (3-13) as the second component:
wherein, in formula (3-1) to formula (3-13), R7 and R8 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkyl having 1 to 12 carbons in which at least one of hydrogen is replaced by fluorine or chlorine, or alkenyl having 2 to 12 carbons in which at least one of hydrogen is replaced by fluorine or chlorine.

### Claim 8 (depends on 6)

The liquid crystal composition according to claim 6, wherein a ratio of the second component is in the range of 10% by weight to 90% by weight based on the weight of the liquid crystal composition.

### Claim 9 (depends on 1)

The liquid crystal composition according to claim 1, containing at least one compound selected from the group of compounds represented by formula (4) as a third component:
wherein, in formula (4), R9 and R10 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one of hydrogen is replaced by fluorine or chlorine; ring E and ring G are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one of hydrogen is replaced by fluorine or chlorine, or tetrahydropyran-2,5-diyl; ring F is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 3,4,5-trifluoronaphthalene-2,6-diyl or 7,8-difluorochroman-2,6-diyl; Z3 and Z4 are independently a single bond, ethylene, carbonyloxy or methyleneoxy; d is 1, 2 or 3, and e is 0 or 1; and a sum of d and e is 3 or less.

### Claim 10 (depends on 9)

The liquid crystal composition according to claim 9, containing at least one compound selected from the group of compounds represented by a formula (4-1) to formula (4-21) as the third component:
wherein, in formula (4-1) to formula (4-21), R9 and R10 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkenyloxy having 2 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one of hydrogen is replaced by fluorine or chlorine.

### Claim 11 (depends on 9)

The liquid crystal composition according to claim 9, wherein a ratio of the third component is in the range of 3% by weight to 25% by weight based on the weight of the liquid crystal composition.

### Claim 12 (depends on 6)

The liquid crystal composition according to claim 6, containing at least one compound selected from the group of compounds represented by formula (4) as a third component:
wherein, in formula (4), R9 and R10 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one of hydrogen is replaced by fluorine or chlorine; ring E and ring G are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one of hydrogen is replaced by fluorine or chlorine, or tetrahydropyran-2,5-diyl; ring F is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4-phenylene, 3,4,5-trifluoronaphthalene-2,6-diyl or 7,8-difluorochroman-2,6-diyl; Z3 and Z4 are independently a single bond, ethylene, carbonyloxy or methyleneoxy; d is 1, 2 or 3, and e is 0 or 1; and a sum of d and e is 3 or less.

### Claim 13 (depends on 12)

The liquid crystal composition according to claim 12, containing at least one compound selected from the group of compounds represented by a formula (4-1) to formula (4-21) as the third component:
wherein, in formula (4-1) to formula (4-21), R9 and R10 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkenyloxy having 2 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one of hydrogen is replaced by fluorine or chlorine.

### Claim 14 (depends on 12)

The liquid crystal composition according to claim 12, wherein a ratio of the third component is in the range of 3% by weight to 25% by weight based on the weight of the liquid crystal composition.

### Claim 15 (depends on 1)

The liquid crystal composition according to claim 1, wherein a maximum temperature of a nematic phase is 70° C. or higher, optical anisotropy (measured at 25° C.) at a wavelength of 589 nanometers is 0.07 or more, and dielectric anisotropy (measured at 25° C.) at a frequency of 1 kHz is 2 or more.

### Claim 16 (depends on 1)

A liquid crystal display device, including the liquid crystal composition according to claim 1.

### Claim 17 (depends on 16)

The liquid crystal display device according to claim 16, wherein an operating mode of the liquid crystal display includes a TN mode, an ECB mode, an OCB mode, an IPS mode, an FFS mode or an FPA mode, and a driving mode of the liquid crystal display device includes an active matrix mode.