# US 7,608,310 B2 · Liquid crystal composition and liquid crystal display device > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,608,310 B2 - Document ID: US7608310B2 - Status: Granted - Kind: B2 - Application number: 11/472,564 - Filed: 2006-06-22 - Published: 2007-01-11 - Granted: 2009-10-27 - Earliest claimed: 2005-06-22 - Assignees: Chisso Corporation; Chisso Petrochemical Corporation - Inventors: Norikatsu Hattori; Hitoshi Yamamoto; Hiroaki Fujita - Web page: https://patentgrep.com/patent/US7608310B2 ## CPC - C09K 19/3001: {Cyclohexane rings} - C09K 19/44: containing compounds with benzene rings directly linked - C09K 2323/00: Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## Abstract The invention provides a liquid crystal composition that satisfies many characteristics among the characteristics such as a wide temperature range of a nematic phase, a small viscosity, a suitable optical anisotropy, a negatively large dielectric anisotropy, and a large specific resistance, and a liquid crystal display device containing the composition. The liquid crystal composition has a negative dielectric anisotropy and contains a first component containing a mono-fluorine-replaced liquid crystal compound having a specific structure and a second component containing a liquid crystal compound having two or more fluorines having a specific structure, and the liquid crystal display device contains the liquid crystal composition. ## Claims ### Claim 1 A liquid crystal composition having a negative dielectric anisotropy and comprising a first component comprising at least one compound selected from the group of compounds represented by formulas (1-1) to (1-3) and a second component comprising at least one compound selected from the group of compounds represented by formulas (2-1) to (2-3): wherein, in formulas (1-1) to (1-3) and formulas (2-1) to (2-3), R11 and R12 are independently alkyl, alkenyl or alkoxy; ring A11 is independently 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene; ring A12 is independently 1,4-cyclohexylene or 1,4-phenylene; ring A13 is independently 1,4-cyclohexylene or 1,4-phenylene, arbitrary hydrogen of which may be replaced by fluorine or chlorine; and Z11 and Z12 are independently a single bond, —C2H4—, —CH2O— or —OCH2—, provided that a compound represented by formula (1-2), wherein ring A11 is 2-fluoro-1,4-phenylene, ring A12 is 1,4-phenylene, and Z11 and Z12 are single bonds, and a compound represented by formula (1-3), wherein ring A11 is 3-fluoro-1,4-phenylene, ring A12 is 1,4-phenylene, and Z11 and Z12 are single bonds, are excluded. ### Claim 2 A liquid crystal composition having a negative dielectric anisotropy and comprising a first component comprising at least one compound selected from the group of compounds represented by formulas (1-1-1), (1-1-2), (1-2-1), (1-2-2), (1-2-3) and (1-3-1) and a second component comprising at least one compound selected from the group of compounds represented by formulas (2-1-1), (2-2-1) and (2-3-1): wherein in formulas (1-1-1), (1-1-2), (1-2-1), (1-2-2), (1-2-3), (1-3-1), (2-1-1), (2-2-1) and (2-3-1), Ra is independently alkyl or alkenyl; Rb is independently alkyl, alkenyl or alkoxy; ring A21 is independently 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene; ring A22 is independently 1,4-cyclohexylene or 1,4-phenylene; ring A23 is 1,4-cyclohexylene or 1,4-phenylene, arbitrary hydrogen of which may be replaced by fluorine; and Z21 is —CH2O— or —OCH2—. ### Claim 3 (depends on 2) The liquid crystal composition according to claim 2, wherein the liquid crystal composition comprises the first component comprising at least one compound selected from a group of compounds represented by formulas (1-1-1), (1-1-2), (1-2-1), (1-2-2) and (1-2-3) and the second component comprising at least one compound selected from the group of compounds represented by formulas (2-1-1), (2-2-1) and (2-3-1). ### Claim 4 (depends on 1) The liquid crystal composition according to claim 1, wherein the a content ratio of the first component is from approximately 10% to approximately 80% by weight, and a content ratio of the second component is from approximately 20% to approximately 90% by weight, based on the total weight of the liquid crystal compounds. ### Claim 5 A liquid crystal composition having a negative dielectric anisotropy and comprising a first component comprising at least one compound selected from the group of compounds represented by formulas (1-1) to (1-3), a second component comprising at least one compound selected from the group of compounds represented by formulas (2-1) to (2-3), and a third component comprising at least one compound selected from the group of compounds represented by formulas (3-1) to (3-3): wherein, in formulas (1-1) to (1-3) and formulas (2-1) to (2-3), R11 and R12 are independently alkyl, alkenyl or alkoxy; ring A11 is independently 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene; ring A12 is independently 1,4-cyclohexylene or 1,4-phenylene; ring A13 is independently 1,4-cyclohexylene or 1,4-phenylene, arbitrary hydrogen of which may be replaced by fluorine or chlorine; and Z11 and Z12 are independently a single bond, —C2H4—, —CH2O— or —OCH2—, wherein in formulas (3-1) to (3-3), Ra is independently alkyl or alkenyl; Rb is independently alkyl, alkenyl or alkoxy; Rc is alkyl, alkenyl, alkoxy or alkoxymethyl; plural rings A22 are independently 1,4-cyclohexylene or 1,4-phenylene; and ring A23 is independently 1,4-cyclohexylene or 1,4-phenylene, arbitrary hydrogen of which may be replaced by fluorine; and Z22 represents a single bond, —CH2O—, —OCH2— or —COO—, provided that a compounds represented by formula (1-2), wherein ring A11 is 2-fluoro-1,4-phenylene, ring A12 is 1,4-phenylene, and Z11 and Z12 are single bonds, and a compound represented by formula (1-3), wherein ring A11 is 3-fluoro-1,4-phenylene, ring A12 is 1,4-phenylene, and Z11 and Z12 are single bonds, are excluded. ### Claim 6 (depends on 5) The liquid crystal composition according to claim 5, wherein a content ratio of the first component is from approximately 5% to approximately 75% by weight, a content ratio of the second component is from approximately 20% to approximately 80% by weight, and a content ratio of the third component is from approximately 5% to approximately 45% by weight, based on the total weight of the liquid crystal compounds. ### Claim 7 A liquid crystal composition having a negative dielectric anisotropy and comprising a first component comprising at least one compound selected from the group of compounds represented by formulas (1-1-1-1), (1-1-1-2), (1-1-2-1), (1-1-2-2), (1-2-1-1), (1-2-1-2), (1-2-2-1), (1-2-3-1) and (1-2-3-2) and a second component comprising at least one compound selected from the group of compounds represented by formulas (2-1-1-1), (2-2-1-1), (2-2-1-2), (2-2-1-3), (2-2-1-4) and (2-2-1-5): wherein in formulas (1-1-1-1), (1-1-1-2), (1-1-2-1), (1-1-2-2), (1-2-1-1), (1-2-1-2), (1-2-2-1), (1-2-3-1), (1-2-3-2), (2-1-1-1), (2-2-1-1), (2-2-1-2), (2-2-1-3), (2-2-1-4) and (2-2-1-5), Ra is independently alkyl or alkenyl; and Rb is independently alkyl, alkenyl or alkoxy. ### Claim 8 (depends on 7) The liquid crystal composition according to claim 7, wherein the liquid crystal composition comprises the first component comprising at least one compound selected from a group of compounds represented by formulas (1-1-1-1), (1-1-2-1), (1-2-1-1) and (1-2-3-1) and the second component comprising at least one compound selected from the group of compounds represented by formulas (2-1-1-1) and (2-2-1-1) to (2-2-1-5). ### Claim 9 (depends on 7) The liquid crystal composition according to claim 7, wherein the liquid crystal composition comprises the first component comprising at least one compound selected from a group of compounds represented by formulas (1-1-1-1), (1-1-1-2), (1-2-1-1), (1-2-1-2) and (1-2-2-1) and the second component comprising at least one compound selected from the group of compounds represented by formulas (2-1-1-1) and (2-2-1-1) to (2-2-1-5). ### Claim 10 (depends on 7) The liquid crystal composition according to claim 7, wherein the liquid crystal composition comprises the first component comprising at least one compound selected from a group of compounds represented by formulas (1-1-1-1), (1-1-2-1), (1-2-1-1) and (1-2-3-1) and the second component comprising at least one compound selected from a group of compounds represented by formulas (2-1-1-1), (2-2-1-1) and (2-2-1-2). ### Claim 11 (depends on 7) The liquid crystal composition according to claim 7, wherein the liquid crystal composition comprises the first component comprising at least one compound selected from a group of compounds represented by formulas (1-1-2-1), (1-1-2-2), (1-2-3-1) and (1-2-3-2) and the second component comprising at least one compound selected from a group of compounds represented by formulas (2-1-1-1), (2-2-1-1) and (2-2-1-2). ### Claim 12 (depends on 7) The liquid crystal composition according to claim 7, wherein the liquid crystal composition comprises the first component comprising at least one compound selected from a group of compounds represented by formulas (1-1-2-1) and (1-2-3-1) and the second component comprising at least one compound selected from the group of compounds represented by formulas (2-1-1-1), (2-2-1-1) and (2-2-1-2). ### Claim 13 (depends on 7) The liquid crystal composition according to claim 7, wherein a content ratio of the first component is from approximately 30% to approximately 75% by weight, and a content ratio of the second component is from approximately 25% to approximately 70% by weight, based on the total weight of the liquid crystal compounds. ### Claim 14 A liquid crystal composition having a negative dielectric anisotropy and comprising a first component comprising at least one compound selected from the group of compounds represented by formulas (1-1-1-1), (1-1-1-2), (1-1-2-1), (1-1-2-2), (1-2-1-1), (1-2-1-2), (1-2-2-1), (1-2-3-1) and (1-2-3-2), a second component comprising at least one compound selected from the group of compounds represented by formulas (2-1-1-1), (2-2-1-1), (2-2-1-2), (2-2-1-3), (2-2-1-4) and (2-2-1-5), and a third component comprising at least one compound selected from the group of compounds represented by formulas (3-1-1), (3-1-2), (3-2-1), (3-3-1) and (3-3-2): wherein in formulas (1-1-1-1), (1-1-1-2), (1-1-2-1), (1-1-2-2), (1-2-1-1), (1-2-1-2), (1-2-2-1), (1-2-3-1), (1-2-3-2), (2-1-1-1), (2-2-1-1), (2-2-1-2), (2-2-1-3), (2-2-1-4) and (2-2-1-5), (3-1-1), (3-1-2), (3-2-1), (3-3-1) and (3-3-2), Ra is independently alkyl or alkenyl; Rb is independently alkyl, alkenyl or alkoxy; and Rc is independently alkyl, alkenyl, alkoxy or alkoxymethyl. ### Claim 15 (depends on 14) The liquid crystal composition according to claim 14, wherein the third component comprises at least one compound selected from a group of compounds represented by formulas (3-1-1), (3-1-2) and (3-2-1). ### Claim 16 (depends on 14) The liquid crystal composition according to claim 14, wherein the third component comprises at least one compound selected from a group of compounds represented by formula (3-2-1). ### Claim 17 (depends on 14) The liquid crystal composition according to claim 14, wherein a content ratio of the first component is from approximately 10% to approximately 65% by weight, a content ratio of the second component is from approximately 25% to approximately 60% by weight, and a content ratio of the third component is from approximately 5% to approximately 35% by weight, based on the total weight of the liquid crystal compounds. ### Claim 18 A liquid crystal composition having a negative dielectric anisotropy and consisting essentially of a first component comprising at least one compound selected from a group of compounds represented by formulas (1-1-1), (1-1-2), (1-2-1), (1-2-2), (1-2-3) and (1-3-1), a second component comprising at least one compound selected from the group of compounds represented by formulas (2-1-1), (2-2-1) and (2-3-1), and a third component comprising at least one compound selected from the group of compounds represented by formulas (3-1) to (3-3): wherein in formulas (1-1-1), (1-1-2), (1-2-1), (1-2-2), (1-2-3), (1-3-1), (2-1-1), (2-2-1), (2-3-1) and (3-1) to (3-3), Ra is independently alkyl or alkenyl; Rb is independently alkyl, alkenyl or alkoxy; Rc is alkyl, alkenyl, alkoxy or alkoxymethyl; ring A21 is independently 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene; ring A22 is independently 1,4-cyclohexylene or 1,4-phenylene; ring A23 is 1,4-cyclohexylene or 1,4-phenylene, arbitrary hydrogen of which may be replaced by fluorine; and Z21 is independently —CH2O— or —OCH2—; Z22 is independently a single bond, —CH2O—, —OCH2— or —COO. ### Claim 19 (depends on 2) The liquid crystal composition according to claim 2, wherein the liquid crystal composition consisting essentially of a first component comprising at least one compound selected from the group of compounds represented by formulas (1-1-1), (1-1-2), (1-2-1), (1-2-2), (1-2-3) and (1-3-1) and a second component comprising at least one compound selected from a group of compounds represented by formulas (2-1-1), (2-2-1) and (2-3-1). ### Claim 20 (depends on 1) The liquid crystal composition according to claim 1, wherein the liquid crystal composition has a dielectric anisotropy in a range of from approximately −6.5 to approximately −2.0. ### Claim 21 (depends on 1) The liquid crystal composition according to claim 1, wherein the liquid crystal composition has an optical anisotropy in a range of approximately 0.080 to approximately 0.120. ### Claim 22 (depends on 1) A liquid crystal display device comprising the liquid crystal composition according to claim 1. ### Claim 23 (depends on 1) The liquid crystal display device according to claim 1, wherein the liquid crystal display device is driven in an active matrix mode and is displayed in a VA mode or an IPS mode.