# US 11,898,012 B2 · Poly(amide-imide) copolymer, composition for preparing poly(amide-imide) copolymer, article including poly(amide-imide) copolymer, and display device including the article > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,898,012 B2 - Document ID: US11898012B2 - Status: Granted - Kind: B2 - Application number: 17/246,926 - Filed: 2021-05-03 - Published: 2021-08-19 - Granted: 2024-02-13 - Earliest claimed: 2017-09-08 - Assignees: Samsung Electronics Co., Ltd.; Samsung SDI Co., Ltd. - Applicants: Samsung Electronics Co., Ltd.; Samsung SDI Co., Ltd. - Inventors: A Ra Jo; Chanjae Ahn; Sungwon Choi; Won Suk Chang; Boreum Jeong - Web page: https://patentgrep.com/patent/US11898012B2 ## CPC - C08G 73/14: Polyamide-imides - B29C 41/003: {characterised by the choice of material} - B29C 41/46: Heating or cooling - C08G 73/1039: {comprising halogen-containing substituents} - C08G 73/1042: {Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds} - C08J 5/18: Manufacture of films or sheets - B29K 2079/08: {PI, i.e. polyimides or derivatives thereof} - B29L 2007/008: {Wide strips, e.g. films, webs} - C08J 2379/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00) - C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29) - B29K: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR {MOULDS, } REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS - B29L: INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES ## Abstract A poly(amide-imide) copolymer that is a reaction product of a substituted or unsubstituted linear aliphatic diamine including two terminals, a diamine represented by Chemical Formula 1, a dicarbonyl compound represented by Chemical Formula 2, and a tetracarboxylic acid dianhydride represented by Chemical Formula 3: NH2-A-NH2 Chemical Formula 1 wherein, in Chemical Formulae 1 to 3, A, R3, R10, R12, R13, X, n7 and n8 are the same as defined in the specification. ## Claims ### Claim 1 A composition for preparing a poly(amide-imide) copolymer comprising a substituted or unsubstituted linear aliphatic diamine, a compound represented by Chemical Formula 4, and a tetracarboxylic acid dianhydride comprising a combination of a compound represented by Chemical Formula 3-1 and a compound represented by Chemical Formula 3-2, and a solvent: wherein, in Chemical Formula 4, R3 is a substituted or unsubstituted phenylene or a substituted or unsubstituted biphenylene group, n0 is a number greater than or equal to 1, and Ar1 and Ar2 are each independently represented by Chemical Formula 5: wherein, in Chemical Formula 5, R6 and R7 are each independently an electron withdrawing group selected from —CF3, —CCl3, —CBr3, —Cl3, —NO2, —CN, —C(═O)CH3, and —CO2C2H5, R8 and R9 are each independently a halogen, a hydroxy group, a substituted or unsubstituted C1 to C10 aliphatic organic group, a substituted or unsubstituted C6 to C20 aromatic organic group, an alkoxy group of formula —OR204, wherein R204 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR205R206R207 wherein —R205, R206, and R207 are each independently hydrogen or a C1 to C10 aliphatic organic group, n3 is an integer ranging from 1 to 4, n5 is an integer ranging from 0 to 3, provided that n3+n5 is an integer ranging from 1 to 4, and n4 is an integer ranging from 1 to 4, n6 is an integer ranging from 0 to 3, provided that n4+n6 is an integer ranging from 1 to 4; ### Claim 2 (depends on 1) The composition for preparing a poly(amide-imide) copolymer according to claim 1, wherein the substituted or unsubstituted linear aliphatic diamine comprises two terminals, wherein the substituted or unsubstituted linear aliphatic diamine comprises an amino group located at each end of the two terminals thereof, and wherein the substituted or unsubstituted linear aliphatic diamine is a substituted or unsubstituted C1 to C30 saturated or unsaturated linear aliphatic diamine. ### Claim 3 (depends on 1) The composition for preparing a poly(amide-imide) copolymer according to claim 1, wherein the substituted or unsubstituted linear aliphatic diamine comprises two terminals, wherein the substituted or unsubstituted linear aliphatic diamine comprises an amino group located at each end of the two terminals thereof, and wherein the substituted or unsubstituted linear aliphatic diamine is a substituted or unsubstituted C1 to C20 saturated linear aliphatic diamine. ### Claim 4 (depends on 1) The composition for preparing a poly(amide-imide) copolymer according to claim 1, wherein the substituted or unsubstituted linear aliphatic diamine is selected from methylene diamine, ethylene diamine, 1,3-propane diamine, 1,4-tetramethylene diamine, 1,5-pentamethylene diamine, 1,6-hexamethylene diamine, 1,7-heptamethylene diamine, 1,8-octamethylene diamine, 1,9-nanomethylene diamine, 1,10-decamehtylene diamine, 1,11-undecamethylene diamine, 1,12-dodecamethylene diamine, and a combination thereof. ### Claim 5 (depends on 1) The composition for preparing a poly(amide-imide) copolymer according to claim 1, wherein the composition further comprises a diamine represented by Chemical Formula 1: NH2-A-NH2 Chemical Formula 1 wherein in Chemical Formula 1, A is a ring system comprising two or more C6 to C30 aromatic rings linked by a single bond, wherein each of the two or more aromatic rings is independently unsubstituted or substituted by an electron-withdrawing group. ### Claim 6 (depends on 5) The composition for preparing a poly(amide-imide) copolymer according to claim 5, wherein the diamine represented by Chemical Formula 1 comprises a ring system comprising two C6 to C12 aromatic rings linked by a single bond, wherein each of the two C6 to C12 aromatic rings are independently substituted by an electron-withdrawing group selected from a halogen atom, a nitro group, a cyano group, a C1 or C2 haloalkyl group, a C2 to C6 alkanoyl group, and a C2 to C6 ester group. ### Claim 7 (depends on 5) The composition for preparing a poly(amide-imide) copolymer according to claim 5, wherein the diamine represented by Chemical Formula 1 comprises at least one selected from the diamines represented by chemical formulae: ### Claim 8 (depends on 5) The composition for preparing a poly(amide-imide) copolymer according to claim 5, wherein the diamine represented by Chemical Formula 1 comprises a diamine represented by Chemical Formula A: ### Claim 9 (depends on 1) The composition for preparing a poly(amide-imide) copolymer according to claim 1, wherein in Chemical Formula 4, R3 is a phenylene group. ### Claim 10 (depends on 1) The composition for preparing a poly(amide-imide) copolymer according to claim 1, wherein the compound represented by Chemical Formula 3-1 comprises 4,4-(hexafluoroisopropylidene)diphthalic anhydride (6FDA), and the compound represented by Chemical Formula 3-2 comprises 3,3′,4,4′-biphenyl tetracarboxylic dianhydride (BPDA). ### Claim 11 (depends on 1) The composition for preparing a poly(amide-imide) copolymer according to claim 1, wherein the compound represented by Chemical Formula 4 is prepared by reacting a diamine represented by Chemical Formula 1 and a dicarbonyl compound represented by Chemical formula 2, and wherein the substituted or unsubstituted linear aliphatic diamine is present in an amount of greater than 20 mole percent and less than 90 mol percent based on the total mole numbers of diamines that include the diamine represented by Chemical Formula 1 to be used to prepare the compound represented by Chemical Formula 4 and the substituted or unsubstituted linear aliphatic diamine present in the composition: NH2-A-NH2 Chemical Formula 1 wherein in Chemical Formula 1, A is a ring system comprising two or more C6 to C30 aromatic rings linked by a single bond, wherein each of the two or more aromatic rings is independently unsubstituted or substituted by an electron-withdrawing group; wherein, in Chemical Formula 2, R3 is a substituted or unsubstituted phenylene or a substituted or unsubstituted biphenylene group, and each X is an identical or different halogen atom. ### Claim 12 (depends on 1) An article comprising a poly(amide-imide) copolymer prepared from the composition according to claim 1. ### Claim 13 (depends on 12) The article according to claim 12, wherein the article comprises a film, and wherein the film has a toughness of greater than or equal to 1,000 Joules×reverse cubic meters×104 (Joul·m−3·104), when the film has a thickness of about 30 micrometers to about 100 micrometers. ### Claim 14 (depends on 1) A window film for a display device comprising a poly(amide-imide) copolymer prepared from the composition according to claim 1. ### Claim 15 (depends on 12) A display device comprising the article according to claim 12. ### Claim 16 (depends on 6) The display device according to claim 6, wherein the display device comprises a flexible display device. ### Claim 17 (depends on 14) A display device comprising the window film according to claim 14.