# US 10,308,735 B2 · Material for organic light-emitting device and organic light-emitting device including the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,308,735 B2 - Document ID: US10308735B2 - Status: Granted - Kind: B2 - Application number: 14/972,853 - Filed: 2015-12-17 - Published: 2016-06-23 - Granted: 2019-06-04 - Earliest claimed: 2014-12-18 - Assignees: Samsung Electronics Co., Ltd. - Applicants: Samsung Electronics Co., Ltd. - Inventors: Masashi Tsuji; Koji Hasegawa; Makoto Taguchi - Web page: https://patentgrep.com/patent/US10308735B2 ## CPC - C08F 32/00: Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system - H10K 85/141: {comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE} - H10K 50/15: Hole transporting layers - H10K 85/151: {Copolymers} - H10K 85/342: {comprising iridium} - H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine} - H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)} - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES ## Abstract A material for an organic light-emitting device, the material including a repeating unit represented by Formula 1: wherein, in Formula 1, R1, A, and X1 are the same as described in the specification. ## Claims ### Claim 1 A material for an organic light-emitting device, the material comprising a repeating unit represented by Formula 1: wherein, in Formula 1, R1 is selected from a single bond, a phenylene group, and a group represented by one of Formulae a1 to a9: wherein, in Formulae a1 to a9, R22 is a C1-C6 alkyl group, X21 and X22 are each independently selected from an oxygen atom and a sulfur atom; A is selected from an adamantylene group, a diadamantylene group, a triadamantylene group, and a tetraadamantylene group; and X1 is a charge transport unit represented by one of Formulae b1 to b13: wherein, in Formulae b1 to b13, R311, R312, R313, R321, R322, R331, R341, R351, R352, R361, R362, R363, R371, R372, R381, R391, R3101, R3111, R3112, R3113, R3121, R3122, R3123, R3124, R3125, R3131 and R3132 are each independently selected from a hydrogen atom, a C1-C6 alkyl group, and a group represented by one of Formulae c1 to c16: wherein, in Formulae c1 to c16, p is 0 or 1; and Z11, Z12, Z21, Z31, Z41, Z42, Z51, Z52, Z53, Z61, Z62, Z71, Z72, Z81, Z82, Z91, and Z92 are each independently selected from a C1-C6 alkyl group, a methoxy group, and a group represented by one of Formulae d1 to d7: wherein, in Formulae d1 to d7, alkyl indicates a C1-C6 alkyl group; Y11, Y12, Y21, Y31, Y41, Y42, Y51, Y52, Y61, Y62, and Y63 are each independently a group represented by one of Formulae e1 to e11: wherein, in Formulae e1 to e11, R411, R412, R421, R431, R441, R442, R451, R452, R461, and R462 are each independently selected from a hydrogen atom, a C1-C6 alkyl group, a phenyl group, and a tolyl group. ### Claim 2 (depends on 1) The material of claim 1, wherein R1 is selected from a phenylene group and a group represented by one of Formulae a1 to a9. ### Claim 3 (depends on 1) The material of claim 1, wherein R1 is selected from a phenylene group and a group represented by Formula a1. ### Claim 4 (depends on 1) The material of claim 1, wherein R1 is a phenylene group. ### Claim 5 (depends on 1) The material of claim 1, wherein X1 is selected from an arylamine moiety, a fluorene moiety, a carbazole moiety, a dibenzofurane moiety, a dibenzothiophene moiety, each optionally forming a fused ring system or a spiro ring system; a fluorenone moiety, a quinone moiety, an anthraquinone moiety, a diphenylquinone moiety, a thiopyrandioxide moiety, an oxazole moiety, an oxadiazole moiety, a triazole moiety, an imidazole moiety, an anthrone moiety, a bipyridine moiety, and a phenanthroline moiety. ### Claim 6 (depends on 1) The material of claim 1, wherein X1 is a group represented by one of Formulae b1 to b5, b8, and b11. ### Claim 7 (depends on 1) The material of claim 1, wherein X1 is a group represented by one of Formulae b1 and b11. ### Claim 8 (depends on 1) The material of claim 1, wherein the repeating unit represented by Formula 1 is represented by Formula 1a: wherein, in Formula 1a, X1 is the same as in Formula 1. ### Claim 9 (depends on 1) The material of claim 1, wherein the material for the organic light-emitting device comprises 20 to 500 repeating units in total. ### Claim 10 (depends on 1) The material of claim 1, wherein the material comprises the repeating unit represented by Formula 1 in an amount of 10 to 100 mol %. ### Claim 11 (depends on 1) The material of claim 1, wherein the material comprises the repeating unit represented by Formula 1 in an amount of 30 to 100 mol %. ### Claim 12 (depends on 1) The material of claim 1, further comprising a repeating unit represented by Formula 2: wherein, in Formula 2, R10 is the same as R1 in claim 1; X10 is the same as X1 in claim 1; and q is 0 or 1. ### Claim 13 (depends on 1) The material of claim 1, wherein the material for the organic light-emitting device is represented by Formula 3: wherein, in Formula 3, R1 and R10 are each independently defined as R1 in Formula 1; A is the same as A in Formula 1; X1 and X10 are each independently defined as X1 in Formula 1; q is 0 or 1; n is an integer of 20 to 500; and m is an integer of 1 to 180. ### Claim 14 (depends on 13) The material of claim 13, wherein n and m satisfy the condition of 0.1≤n/(n+m)≤1. ### Claim 15 (depends on 13) The material of claim 13, wherein n and m satisfy the condition of 20≤n+m≤500. ### Claim 16 An organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode; wherein the organic layer comprises the material comprising: a repeating unit represented by Formula 1: wherein, in Formula 1, R1 is selected from a single bond, a phenylene group, and a group represented by one of Formulae a1 to a9: wherein, in Formulae a1 to a9, R22 is a C1-C6 alkyl group, X21 and X22 are each independently selected from an oxygen atom and a sulfur atom; A is selected from an adamantylene group, a diadamantylene group, a triadamantylene group, and a tetraadamantylene group; and X1 is a charge transport unit represented by one of Formulae b1 to b13: wherein, in Formulae b1 to b13, R311, R312, R313, R321, R322, R331, R341, R351, R352, R361, R362, R363 , R371, R372, R381, R391, R3101, R3111, R3112, R3113, R3121, R3122, R3123, R3124,R3125, R3131 and R3132 are each independently selected from a hydrogen atom, a C1-C6 alkyl group, and a group represented by one of Formulae c1 to c16: wherein, in Formulae c1 to c16, p is 0 or 1; and Z11, Z12, Z21, Z31, Z41, Z42, Z51, Z52, Z53, Z61, Z62, Z71, Z72, Z81, Z82, Z91, and Z92 are each independently selected from a C1-C6 alkyl group, a methoxy group, and a group represented by one of Formulae d1 to d7: wherein, in Formulae d1 to d7, alkyl indicates a C1-C6 alkyl group; Y11, Y12, Y21, Y31, Y41, Y42, Y51, Y52, Y61, Y62, and Y63 are each independently a group represented by one of Formulae e1 to e11: wherein, in Formulae e1 to e11, R411, R412, R421, R431, R441, R442, R451, R452, R461, and R462 are each independently selected from a hydrogen atom, a C1-C6 alkyl group, a phenyl group, and a tolyl group. ### Claim 17 (depends on 16) The organic light-emitting device of claim 16, wherein the organic film comprises at least one layer selected from a hole injection layer and a hole transport layer; and the at least one layer comprises the material.