# US 8,568,839 B2 · Liquid crystal composition and retardation film > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,568,839 B2 - Document ID: US8568839B2 - Status: Granted - Kind: B2 - Application number: 12/569,225 - Filed: 2009-09-29 - Published: 2010-04-01 - Granted: 2013-10-29 - Earliest claimed: 2008-09-30 - Assignees: FUJIFILM Corporation - Applicants: Hiroshi Takeuchi; Mitsuyoshi Ichihashi; Ryo Hamasaki - Inventors: Hiroshi Takeuchi; Mitsuyoshi Ichihashi; Ryo Hamasaki - Web page: https://patentgrep.com/patent/US8568839B2 ## CPC - C09K 19/32: containing condensed ring systems, i.e. fused, bridged or spiro ring systems - C09K 19/2007: {the chain containing -COO- or -OCO- groups} - C09K 19/3066: {in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers} - C09K 19/322: {Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring} - C09K 19/3411: {the heterocyclic ring being a three-membered ring} - C09K 2019/0407: {containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone} - C09K 2019/0448: {the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate} - C09K 2019/0466: {the linking chain being a -CF2O- chain} - C09K 2019/3408: {Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems} - C09K 2019/3416: {the heterocyclic ring being a four-membered ring, e.g. oxetane} - 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 relates to a liquid crystal composition comprising two or more species of liquid crystal compounds respectively having a polymerizable group, at least one species of which being a compound represented by formula (I) below, having a content of the compound of from 20% to 80% relative to the total mass of said two or more species of liquid crystal compounds. In formula (I), P1 represents a polymerizable group; each of L1 and L2 represents a divalent spacer group; each of Z1 to Z4 represents a divalent linking group; each of A1 and A2 represents a divalent cyclic group; each of m and n represents an integer from 0 to 3; MA represents any one group of A-I to A-V below: ## Claims ### Claim 1 A retardation film comprising a liquid crystal composition comprising two or more species of liquid crystal compounds respectively having a polymerizable group, at least one species of which being a compound represented by formula (I) below, having a content of the compound represented by the formula (I) of from 20% by mass to 80% by mass relative to the total mass of said two or more species of liquid crystal compounds: P1-L1-(Z1-A1)m-Z3-MA-Z4-(A2-Z2)n-L2-R0 Formula (I) where, P1 represents a polymerizable group; each of L1 and L2 independently represents a divalent spacer group; each of Z1 to Z4 independently represents a divalent linking group; each of A1 and A2 independently represents a divalent cyclic group; each of m and n independently represents an integer from 0 to 3; R0 represents a hydrogen atom or substituent; MA represents any one group selected from the group consisting of M-1, M-5, M-6, M-8, M-9 and M-11 below: ### Claim 2 (depends on 1) The retardation film according to claim 1, wherein the content of the compound represented by formula (I) is from 40% by mass to 80% by mass relative to the total mass of said two or more species of liquid crystal compounds. ### Claim 3 (depends on 1) The retardation film according to claim 1, wherein R0 in formula (I) represents a hydrogen atom, alkyl group or polymerizable group. ### Claim 4 (depends on 1) The retardation film according to claim 1, wherein P1 in formula (I) represents a group represented by any one of formulae P1, P2, P3 and P4 below: where, each of R511, R512, R513, R521, R522, R523, R531, R532, R533, R541, R542, R543, R544 and R545 independently represents a hydrogen atom or alkyl group, and n represents 0 or 1. ### Claim 5 (depends on 1) The retardation film according to claim 1, wherein MA in formula (I) represents M-1. ### Claim 6 (depends on 1) The retardation film according to claim 1, wherein each of A1 and A2 is a substituted or non-substituted phenyl group, or substituted or non-substituted cyclohexyl group. ### Claim 7 (depends on 1) The retardation film according to claim 1, wherein each of Z1 to Z4 in formula (I) independently represents a single bond or a group selected from the group consisting of —O—CF2—, alkylene group having 1 to 6 carbon atoms, and —≡—. ### Claim 8 (depends on 1) The retardation film according to claim 1, wherein each of L1 and L2 in formula (I) independently represents a single bond, or alkylene group having 1 to 20 carbon atoms, provided that, in the alkylene group, an arbitrary —CH2— may be replaced by —O—, —S—, —COO—, —OCO—, —CH═CH—, —CF═CF— or —C≡C—, and an arbitrary hydrogen atom may be replaced by a halogen atom. ### Claim 9 (depends on 1) The retardation film according to claim 1, comprising a compound represented by formula (II) below, with a content of 20% by mass or more and 80% by mass or less relative to the total mass of said two species or more of liquid crystal compounds: P11-L11-(Z11-A11)m-Z13-MB-Z14-(A12-Z12)n-L12-R10 Formula (II) where, P11 represents a polymerizable group; each of L11 and L12 independently represents a divalent spacer group; each of Z11 to Z14 independently represents a divalent linking group; each of A11 and A12 independently represents a divalent cyclic group; each of m and n represents an integer from 0 to 3; MB represents any one group of B-I to B-III below: wherein each of R11 to R18 independently represents a hydrogen atom, bromine atom, —CN, —COR wherein R represents a hydrogen atom or alkyl group having 1 to 6 carbon atoms, —COOR wherein R represents a hydrogen atom or alkyl group having 1 to 6 carbon atoms, alkyl group having 1 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, or alkenyl group having 1 to 6 carbon atoms; and R10 represents a hydrogen atom or substituent. ### Claim 10 (depends on 9) The retardation film according to claim 9, wherein the compound represented by formula (II) has no fluorine atom. ### Claim 11 (depends on 9) The retardation film according to claim 9, wherein MB in formula (II) represents any one of B-1 to B-12: ### Claim 12 (depends on 9) The retardation film according to claim 9, wherein R10 in formula (II) represents a hydrogen atom, alkyl group or polymerizable group. ### Claim 13 (depends on 9) The retardation film according to claim 9, wherein P11 in formula (II) represents a group represented by any one of formulae P1, P2, P3 and P4 below: where, each of R511, R512, R513, R521, R522, R523, R531, R532, R533, R541, R542, R543, R544 and R545 independently represents a hydrogen atom or alkyl group, and n represents 0 or 1. ### Claim 14 (depends on 9) The retardation film according to claim 9, wherein each of A11 and A12 is a substituted or non-substituted phenyl group, or substituted or non-substituted cyclohexyl group. ### Claim 15 (depends on 9) The retardation film according to claim 9, wherein each of Z11 to Z14 in formula (II) independently represents a single bond or a group selected from the group consisting of —O—CF2—, alkylene group having 1 to 6 carbon atoms, and —≡—. ### Claim 16 (depends on 9) The retardation film according to claim 9, wherein each of L11 and L12 in formula (II) independently represents a single bond, or alkylene group having 1 to 20 carbon atoms, provided that, in the alkylene group, an arbitrary —CH2— may be replaced by —O—, —S—, —COO—, —OCO—, —CH═CH—, —CF═CF— or —C≡C—, and an arbitrary hydrogen atom may be replaced by a halogen atom.