# US 12,225,814 B2 · Compound for organic optoelectronic diode, composition for organic optoelectronic diode, organic optoelectronic diode and display device > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,225,814 B2 - Document ID: US12225814B2 - Status: Granted - Kind: B2 - Application number: 16/955,128 - Filed: 2018-12-31 - Published: 2020-12-10 - Granted: 2025-02-11 - Earliest claimed: 2017-12-29 - Assignees: Samsung SDI Co., Ltd. - Applicants: Samsung SDI Co., Ltd. - Inventors: Changwoo Kim; Seungjae Lee; Hyung Sun Kim; Dong Wan Ryu; Chang Ju Shin; Kipo Jang; Sung-Hyun Jung; Juyeon Jung; Handong Chu - Web page: https://patentgrep.com/patent/US12225814B2 ## CPC - H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)} - C07D 405/14: containing three or more hetero rings - C09K 11/06: containing organic luminescent materials - H10K 85/342: {comprising iridium} - H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes} - C09K 2211/1029: containing one nitrogen atom as the heteroatom - C09K 2211/1033: with oxygen - C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - H10K 2101/10: Triplet emission - H10K 2101/90: {Multiple hosts in the emissive layer} - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## Abstract Provided are: a compound for an organic optoelectronic diode; a composition for an organic optoelectronic diode including the same; an organic optoelectronic diode including the composition for the organic optoelectronic diode as a host; and a display device including the organic optoelectronic diode. ## Claims ### Claim 1 A compound for an organic optoelectronic diode represented by Chemical Formula 1: wherein, in Chemical Formula 1, Ar1 is an unsubstituted biphenyl group or an unsubstituted terphenyl group, Ar2 is represented by one of Chemical Formula 2A, Chemical Formula 3A, and Chemical Formula 4A, and Ar3 is represented by Chemical Formula 2B or Chemical Formula 4B, wherein, in Chemical Formula 2A, Chemical Formula 3A, Chemical Formula 4A, Chemical Formula 2B and Chemical Formula 4B, X is O, R1 and R2 are independently an unsubstituted phenyl group, R1 is bonded to the moiety that includes X at the 1 or 4 position, R2 is bonded to the moiety that includes X at the 9 position, m1 and m2 are each 0, m3 and m4 are each independently 0 or 1, and m1+m2+m3+m4=1, and * is a linking point. ### Claim 2 (depends on 1) The compound for the organic optoelectronic diode of claim 1, wherein Ar2 is represented by Chemical Formula 2-3, Chemical Formula 3-3, or Chemical Formula 4-2 and Ar3 is represented by Chemical Formula 2-1, Chemical Formula 2-2, or Chemical Formula 4-1: wherein, in Chemical Formula 2-1, Chemical Formula 2-2, Chemical Formula 2-3, Chemical Formula 3-3, Chemical Formula 4-1, and Chemical Formula 4-2, X is O, R1 and R2 are independently an unsubstituted phenyl group, m1 and m2 are each 0, and * is a linking point. ### Claim 3 (depends on 1) The compound for the organic optoelectronic diode of claim 1, wherein the compound for an organic optoelectronic diode represented by Chemical Formula 1 is selected from compounds of Group 1: ### Claim 4 (depends on 1) A composition for an organic optoelectronic diode comprising the compound of claim 1. ### Claim 5 (depends on 4) An organic optoelectronic diode, comprising an anode and a cathode facing each other, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises at least one of a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, and the light emitting layer comprises the composition for an organic optoelectronic diode of claim 4 as a first host. ### Claim 6 (depends on 5) The organic optoelectronic diode of claim 5, wherein the light emitting layer further comprises a compound represented by a combination of Chemical Formula 6 and Chemical Formula 7 as a second host: wherein, in Chemical Formula 6 to Chemical Formula 7, Y1 and Y2 are independently a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, adjacent two *'s of Chemical Formula 6 are linked to Chemical Formula 7, *'s of Chemical Formula 6 not linked to Chemical Formula 7 is independently C-La-Rb, La, L3, and L4 are independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and Rb and R5 to R8 are independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group. ### Claim 7 (depends on 6) The organic optoelectronic diode of claim 6, wherein the compound represented by the combination of Chemical Formula 6 and Chemical Formula 7 is represented by one of Chemical Formula 6A, Chemical Formula 6B, Chemical Formula 6C, and Chemical Formula 6D: wherein, in Chemical Formula 6A to Chemical Formula 6D, Y1 and Y2 are independently a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, La1 to La4, L3, and L4 are independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and Rb1 to Rb4 and R5 to R8 are independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group. ### Claim 8 (depends on 7) The organic optoelectronic diode of claim 7, wherein Y1 and Y2 are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and Rb1 to Rb4 and R5 to R8 are independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. ### Claim 9 (depends on 5) The organic optoelectronic diode of claim 5, wherein the organic optoelectronic diode further comprises a phosphorescent dopant represented by Chemical Formula 8: wherein, in Chemical Formula 8, Z4 to Z11 are independently N, C or CRc, the ring C is bound to the ring B through a C—C bond, iridium is bound to the ring B through a Ir—C bond, X2 is O or S, Rc and R14 to R19 are independently hydrogen, deuterium, a halogen, germanium group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and n is one of integers of 1 to 3. ### Claim 10 (depends on 9) The organic optoelectronic diode of claim 9, wherein Chemical Formula 8 is represented by one of Chemical Formula 8-1 to Chemical Formula 8-6: wherein, in Chemical Formula 4-1 to Chemical Formula 4-6, X2 is O or S, Rc1, Rc2, Rc3, and R14 to R19 are independently hydrogen, deuterium, a halogen, germanium group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and n is one of integers of 1 to 3. ### Claim 11 (depends on 5) A display device comprising the organic optoelectronic diode of claim 5. ### Claim 12 (depends on 6) The organic optoelectronic diode of claim 6, wherein, in Chemical Formula 6 and Chemical Formula 7, moiety -L3-Y1 and moiety -L4-Y2 do not include a terphenyl group. ### Claim 13 (depends on 6) The organic optoelectronic diode of claim 6, wherein the compound represented by the combination of Chemical Formula 6 and Chemical Formula 7 is represented by Chemical Formula 6A or Chemical Formula 6B: wherein, in Chemical Formula 6A and Chemical Formula 6B, Y1 and Y2 are independently a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, La1, La3, La4, L3, and L4 are independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and Rb1, Rb3, Rb4 and R5 to R8 are independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group. ### Claim 14 (depends on 1) The compound for the organic optoelectronic diode of claim 1, wherein the compound for an organic optoelectronic diode represented by Chemical Formula 1 is selected from compounds of Group 2: