# US 9,520,569 B2 · Aryl compounds for application in a highly polar solvent > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,520,569 B2 - Document ID: US9520569B2 - Status: Granted - Kind: B2 - Application number: 14/351,317 - Filed: 2012-10-11 - Published: 2014-08-21 - Granted: 2016-12-13 - Earliest claimed: 2011-10-17 - Assignees: Sumitomo Chemical Company, Limited - Applicants: Sumitomo Chemical Company, Limited - Inventors: Ken Sakakibara; Masanobu Tanaka; Rui Ishikawa; Hideyuki Higashimura - Web page: https://patentgrep.com/patent/US9520569B2 ## CPC - H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine} - C07C 229/64: the carbon skeleton being further substituted by singly-bound oxygen atoms - C08G 61/12: Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule - C08L 65/00: Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08L7/00 - C08L57/00, C08L61/00 take precedence); Compositions of derivatives of such polymers - C09D 165/00: Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C09D107/00 - C09D157/00, C09D161/00 take precedence); Coating compositions based on derivatives of such polymers - H01B 1/12: organic substances {(organic macromolecular compounds or compositions C08)} - H10K 85/111: {comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene} - H10K 85/115: {Polyfluorene; Derivatives thereof} - H10K 85/151: {Copolymers} - H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene} - H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom} - H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)} - H10K 85/655: {comprising only sulfur as heteroatom} - C08G 2261/135: Cross-linked structures - C08G 2261/1412: Saturated aliphatic units - C08G 2261/1424: containing ether groups, including alkoxy - C08G 2261/1426: containing carboxy groups (COOH) and/or -C(=O)O-moieties - C08G 2261/3142: fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene - C08G 2261/3162: Arylamines - C08G 2261/411: Suzuki reactions - C08G 2261/5222: electrofluorescent - C08G 2261/5242: electrophosphorescent - C08G 2261/76: crosslinking - C08G 2261/91: Photovoltaic applications - C08G 2261/95: Use in organic luminescent diodes - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 50/15: Hole transporting layers - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) - H01B: CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES (selection for magnetic properties H01F1/00; waveguides H01P {; printed circuits H05K}) ## Abstract The present invention provides a compound that has high solubility in a highly polar solvent and is usefully usable for an application method using a highly polar solvent, the compound that can manufacture an electroluminescent device having high light-emitting efficiency. Specifically, the present invention provides a compound containing a structure represented by Formula (1): wherein: Ar1, Ar2, Ar3, and Ar4 each independently represent a divalent aromatic group optionally having substituent(s); Ar5 represents a monovalent aromatic group optionally having substituent(s); p and q each independently represent an integer of 0 or more; and R1 represents a given monovalent group. ## Claims ### Claim 1 A polymer compound comprising a structure represented by Formula (1) as a constitutional unit: wherein: Ar1, Ar2, Ar3, and Ar4 each independently represent a divalent aromatic group optionally having substituent(s) and may be bonded to each other to form a ring, when more than one Ar2 is present, such Ar2s may be the same as or different from each other, and when more than one Ar4 is present, such Ar4s may be the same as or different from each other; Ar5 represents a monovalent aromatic group optionally having substituent(s), and when more than one Ar5 is present, such Ar5s may be the same as or different from each other; p and q each independently represent an integer of 0 or more; and R1 represents a monovalent group represented by Formula (2), and when more than one R1 is present, such R1s may be the same as or different from each other: wherein: R2 represents a (1+n1+n4)-valent aromatic group optionally having substituent(s); R3 represents a divalent organic group optionally having substituent(s); R4 represents a divalent organic group comprising a structure which is capable of interacting with a cation through chelation, and when more than one R4 is present, such R4s may be bonded to each other to form a ring; R5 is an optionally substituted monovalent organic group remaining after removing one hydrogen atom from a compound represented by a formula selected from the group consisting of formulas 3-1 to 3-4 and 3-6 to 3-27, and when more than one R5 is present, such R5s may be bonded to each other to form a ring: Y1 represents a monovalent group comprising an anion; n1 represents 1 or 2, n2 represents 0 or 1, n3 represents an integer of 0 or more, n4 represents an integer of 1 or more, and n1+n3≧1 is satisfied, when more than one R3 is present, such R3s may be the same as or different from each other, when more than one R4 is present, such R4s may be the same as or different from each other, when more than one R5 is present, such R5s may be the same as or different from each other, and when more than one Y1 is present, such Y1s may be the same as or different from each other; M1 represents a cation; Z1 represents an anion; a represents an integer of 1 or more, and b represents an integer of 0 or more, provided that a and b are selected so that electric charge of the structure represented by Formula (1) becomes zero; and when more than one M1 is present, such M1s may be the same as or different from each other, and when more than one Z1 is present, such Z1s may be the same as or different from each other. ### Claim 2 (depends on 1) The polymer compound according to claim 1, wherein the group represented by Y1 is a group selected from —CO2−, —SO2−, —SO3−, —O−, PO32−, and —BRa3−, wherein Ra represents a hydrogen atom or a monovalent organic group, and a plurality of Ras may be the same as or different from each other and may be bonded to each other to form a ring. ### Claim 3 (depends on 2) The polymer compound according to claim 2, wherein the group represented by Y1 is a group represented by —CO2−. ### Claim 4 (depends on 1) The polymer compound according to claim 1, wherein M1 is a cation selected from Li+, Na+, K+, Rb+, Cs+, and (Rb)4N+, wherein Rb represents a hydrogen atom or a monovalent organic group, and a plurality of Rbs may be the same as or different from each other and may be bonded to each other to form a ring. ### Claim 5 (depends on 1) The polymer compound according to claim 1, wherein the group represented by R4 is a divalent organic group having two or more oxygen atoms. ### Claim 6 (depends on 1) The polymer compound according to claim 1, wherein the groups represented by Ar1, Ar2, Ar3, and Ar4 are each a phenylene group optionally having substituent(s). ### Claim 7 (depends on 1) The polymer compound according to claim 1, wherein the group represented by R2 is a (1+n1+n4)-valent group optionally having substituent(s), wherein the (1+n1+n4)-valent group optionally having substituent(s) is a remainder of a benzene ring optionally having substituent(s) from which (1+n1+n4) hydrogen atoms bonded to the benzene ring are removed. ### Claim 8 (depends on 1) The polymer compound according to claim 1, wherein q is 0. ### Claim 9 (depends on 8) The polymer compound according to claim 8, comprising a structure represented by Formula (3) as a constitutional unit: wherein: p represents an integer of 0 or more; M1 represents a cation; n5 and n8 each independently represent 1, 2, 3, or 4; n6, n7, n9, and n10 each independently represent an integer of 1 to 4, and n6+n7≦5 and n9+n10≦5 are satisfied. ### Claim 10 (depends on 9) The polymer compound according to claim 9, comprising a structure represented by Formula (4) as a constitutional unit: wherein M1 represents a cation, and n5 represents 1, 2, 3, or 4. ### Claim 11 (depends on 1) A composition comprising: the polymer compound according to claim 1; and at least one material selected from the group consisting of a hole transport material, an electron transport material, and a light-emitting material. ### Claim 12 (depends on 1) A stacked structure comprising the polymer compound according to claim 1. ### Claim 13 (depends on 12) The stacked structure according to claim 12, wherein the stacked structure is an electroluminescent device. ### Claim 14 (depends on 12) The stacked structure according to claim 12, wherein the stacked structure is a photoelectric conversion device. ### Claim 15 A polymer compound comprising a structure represented by Formula (5) as a constitutional unit: wherein n5 represents an integer of 1 or more, and R6 represents a monovalent organic group. ### Claim 16 A compound represented by Formula (6): wherein: n5 represents an integer of 1 or more, and R6 represents a monovalent organic group; X represents a chlorine atom, a bromine atom, an iodine atom, a p-toluenesulfonate group, a trifluoromethanesulfonate group, a methanesulfonate group, a dihydroxyboryl group, or a dialkoxyboryl group, and the two X may be the same as or different from each other. ### Claim 17 A compound represented by Formula (7): wherein: R6 represents a monovalent organic group; and X represents a chlorine atom, a bromine atom, an iodine atom, a p-toluenesulfonate group, a trifluoromethanesulfonate group, a methanesulfonate group, a dihydroxyboryl group, or a dialkoxyboryl group, and the two X may be the same as or different from each other.