# US 2013/0155360 A1 · Liquid crystal display device and method of manufacturing the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2013/0155360 A1 - Document ID: US20130155360A1 - Status: Published application - Kind: A1 - Application number: 13/709,085 - Filed: 2012-12-10 - Published: 2013-06-20 - Earliest claimed: 2011-12-16 - Assignees: Sony Corporation - Inventors: Seiji Shibahara; Shunichi Suwa; Masashi Miyakawa; Masahiko Nakamura; Tadaaki Isozaki - Web page: https://patentgrep.com/patent/US20130155360A1 ## CPC - G02F 1/1337: Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers - C08G 73/1078: {wholly aromatic in the diamino moiety} - C09K 19/56: Aligning agents - G02F 1/133788: {by light irradiation, e.g. linearly polarised light photo-polymerisation} - G02F 1/133715: {by first depositing a monomer} - G02F 1/13712: {the liquid crystal having negative dielectric anisotropy} - G02F: OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## Abstract A liquid crystal display device includes a liquid crystal display element including a pair of alignment films provided on opposing face sides of a pair of substrates, and a liquid crystal layer including liquid crystal molecules with negative dielectric constant anisotropy provided between the pair of alignment films, wherein at least one of the pair of alignment films includes a compound in which a polymer compound including a cross-linkable functional group as a side chain is cross-linked, a pretilt is conferred on the liquid crystal molecules by the cross-linked compound, and at least one type of a compound represented by the following General Formula 101 or General Formula 102 is included in the liquid crystal layer. CH(4-n)(R1)n (101) (R2)m-A-(X)p (102) ## Claims ### Claim 1 A liquid crystal display device comprising: a liquid crystal display element including a pair of alignment films provided on opposing face sides of a pair of substrates, and a liquid crystal layer including liquid crystal molecules with negative dielectric constant anisotropy provided between the pair of alignment films, wherein at least one of the pair of alignment films includes a compound in which a polymer compound including a cross-linkable functional group as a side chain is cross-linked, a pretilt is conferred on the liquid crystal molecules by the cross-linked compound, and at least one type of a compound represented by a following General Formula 101 or General Formula 102 is included in the liquid crystal layer, CH(4-n)(R1)n (101) (R2)m-A-(X)p (102). wherein in General Formula 101, R1 represents a phenyl group or a cyclohexyl group which may be respectively independently substituted and n is 3 or 4, and in General Formula 102, “A” represents a benzene ring or a cyclohexane ring, R2 represents a phenyl group, a cyclopentadienyl group, or a naphthyl group which may be respectively independently substituted, X respectively independently represents a halogen atom, m is 3, and p is an integer between 0 and 3. ### Claim 2 A liquid crystal display device comprising: a liquid crystal display element including a pair of alignment films provided on opposing face sides of a pair of substrates, and a liquid crystal layer including liquid crystal molecules with negative dielectric constant anisotropy provided between the pair of alignment films, wherein at least one of the pair of alignment films includes a compound in which a polymer compound including a photosensitive functional group as a side chain is deformed, a pretilt is conferred on the liquid crystal molecules by the deformed compound, and at least one type of a compound represented by a following General Formula 101 or General Formula 102 is included in the liquid crystal layer, CH(4-n)(R1)n (101) (R2)m-A-(X)p (102). wherein in General Formula 101, R1 represents a phenyl group or a cyclohexyl group which may be respectively independently substituted and n is 3 or 4, and in General Formula 102, “A” represents a benzene ring or a cyclohexane ring, R2 represents a phenyl group, a cyclopentadienyl group, or a naphthyl group which may be respectively independently substituted, X respectively independently represents a halogen atom, m is 3, and p is an integer between 0 and 3. ### Claim 3 (depends on 1) The liquid crystal display device according to claim 1, wherein a substituent in R1 or R2 of the compound represented by General Formula 101 or General Formula 102 is at least one type selected from the group consisting of a halogen atom, a hydrocarbon group with one to eight carbon atoms, and an alkoxy group with one to six carbon atoms. ### Claim 4 (depends on 3) The liquid crystal display device according to claim 3, wherein the halogen atom is a fluorine atom or a chlorine atom. ### Claim 5 (depends on 1) The liquid crystal display device according to claim 1, wherein a mass ratio of the compound represented by General Formula 101 or General Formula 102 with respect to a total of the compound represented by General Formula 101 or General Formula 102 and the liquid crystal molecules is 0.1 mass % to 5 mass %. ### Claim 6 (depends on 1) The liquid crystal display device according to claim 1, wherein a compound configuring at least one of the pair of alignment films is further formed by a compound including a group represented by Formula 1 as a side chain, —R1—R2—R3 (1) here, R1 is a linear or branched divalent organic group with three or more carbon atoms which is coupled with a main chain of the polymer compound, R2 is a divalent organic group including a plurality of ring structures in which one of the atoms configuring the ring structures is coupled with R1, and R3 is a monovalent group including a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, and a carbonate group, or a derivative thereof. ### Claim 7 (depends on 1) The liquid crystal display device according to claim 1, wherein a compound configuring at least one of the pair of alignment films is further formed by a compound including a group represented by Formula 2 as a side chain, —R11—R12—R13—R14 (2) here, R11 is a linear or branched divalent organic group with one or more and twenty or fewer carbon atoms, and preferably three or more and twelve or fewer carbon atoms including an ether group or an ester group which is coupled with a main chain of the polymer compound, or R11 is an ether group or an ester group which is coupled with the main chain of the polymer compound, R12 is a divalent group including any one type of structure out of chalcone, cinnamate, cinnamoyl, coumarin, maleimide, benzophenone, norbornene, oryzanol, and chitosan, or is an ethynylene group, R13 is a divalent organic group including a plurality of ring structures, and R14 is a monovalent group including a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, and a carbonate group, or a derivative thereof. ### Claim 8 (depends on 1) The liquid crystal display device according to claim 1, wherein the compound obtained by cross-linking the polymer compound is configured by a side chain and a main chain supporting the side chain with respect to the substrates, the side chain is configured by a cross-linked portion coupled to the main chain and in which a portion of the side chain is cross-linked and a terminal structure portion coupled to the cross-linked portion, and a pretilt is conferred by the liquid crystal molecules being along the terminal structure portion or being interposed by the terminal structure portion. ### Claim 9 (depends on 2) The liquid crystal display device according to claim 2, wherein the compound obtained by deforming the polymer compound is configured by a side chain and a main chain supporting the side chain with respect to the substrates, the side chain is configured by a deformed portion coupled to the main chain and in which a portion of the side chain is deformed and a terminal structure portion coupled to the deformed portion, and a pretilt is conferred by the liquid crystal molecules being along the terminal structure portion or being interposed by the terminal structure portion. ### Claim 10 (depends on 1) The liquid crystal display device according to claim 1, wherein the compound obtained by cross-linking the polymer compound is configured by a side chain and a main chain supporting the side chain with respect to the substrates, and the side chain is configured by a cross-linked portion coupled to the main chain and in which a portion of the side chain is cross-linked and a terminal structure portion coupled to the cross-linked portion, including a mesogenic group. ### Claim 11 (depends on 2) The liquid crystal display device according to claim 2, wherein the compound obtained by deforming the polymer compound is configured by a side chain and a main chain supporting the side chain with respect to the substrates, and the side chain is configured by a deformed portion coupled to the main chain and in which a portion of the side chain is deformed and a terminal structure portion coupled to the deformed portion, including a mesogenic group. ### Claim 12 (depends on 1) The liquid crystal display device according to claim 1, wherein a surface roughness Ra of at least one of the pair of alignment films is equal to or less than 1 nm. ### Claim 13 (depends on 1) The liquid crystal display device according to claim 1, wherein the pair of alignment films have a same composition. ### Claim 14 (depends on 1) The liquid crystal display device according to claim 1, wherein an alignment regulation unit formed of a slit formed on an electrode or a protrusion provided on a substrate is provided. ### Claim 15 A method of manufacturing a liquid crystal display device, the method comprising: forming a first alignment film formed of a polymer compound including a cross-linkable functional group as a side chain on one of a pair of substrates; forming a second alignment film on an other of the pair of substrates; arranging the pair of substrates so that the first alignment film and the second alignment film are opposing, and sealing a liquid crystal layer including liquid crystal molecules with negative dielectric constant anisotropy and at least one type of compound represented by a following General Formula 101 or General Formula 102 between the first alignment film and the second alignment film; and conferring a pretilt on the liquid crystal molecules by cross-linking the polymer compound after sealing the liquid crystal layer, CH(4-n)(R1)n (101) (R2)m-A-(X)p (102). wherein in General Formula 101, R1 represents a phenyl group or a cyclohexyl group which may be respectively independently substituted and n is 3 or 4, and in General Formula 102, “A” represents a benzene ring or a cyclohexane ring, R2 represents a phenyl group, a cyclopentadienyl group, or a naphthyl group which may be respectively independently substituted, X respectively independently represents a halogen atom, m is 3, and p is an integer between 0 and 3. ### Claim 16 A method of manufacturing a liquid crystal display device, the method comprising: forming a first alignment film formed of a polymer compound including a photosensitive functional group as a side chain on one of a pair of substrates; forming a second alignment film on an other of the pair of substrates; arranging the pair of substrates so that the first alignment film and the second alignment film are opposing, and sealing a liquid crystal layer including liquid crystal molecules with negative dielectric constant anisotropy and at least one type of compound represented by a following General Formula 101 or General Formula 102 between the first alignment film and the second alignment film; and conferring a pretilt on the liquid crystal molecules by deforming the polymer compound after sealing the liquid crystal layer, CH(4-n)(R1)n (101) (R2)m-A-(X)p (102). wherein in General Formula 101, R1 represents a phenyl group or a cyclohexyl group which may be respectively independently substituted and n is 3 or 4, and in General Formula 102, “A” represents a benzene ring or a cyclohexane ring, R2 represents a phenyl group, a cyclopentadienyl group, or a naphthyl group which may be respectively independently substituted, X respectively independently represents a halogen atom, m is 3, and p is an integer between 0 and 3. ### Claim 17 A method of manufacturing a liquid crystal display device, the method comprising: forming a first alignment film formed of a polymer compound including a cross-linkable functional group or a photosensitive functional group as a side chain on one of a pair of substrates; forming a second alignment film on an other of the pair of substrates; arranging the pair of substrates so that the first alignment film and the second alignment film are opposing, and sealing a liquid crystal layer including liquid crystal molecules with negative dielectric constant anisotropy and at least one type of compound represented by a following General Formula 101 or General Formula 102 between the first alignment film and the second alignment film; and conferring a pretilt on the liquid crystal molecules by irradiating energy rays on the polymer compound after sealing the liquid crystal layer, CH(4-n)(R1)n (101) (R2)m-A-(X)p (102). wherein in General Formula 101, R1 represents a phenyl group or a cyclohexyl group which may be respectively independently substituted and n is 3 or 4, and in General Formula 102, “A” represents a benzene ring or a cyclohexane ring, R2 represents a phenyl group, a cyclopentadienyl group, or a naphthyl group which may be respectively independently substituted, X respectively independently represents a halogen atom, m is 3, and p is an integer between 0 and 3.