# US 10,319,921 B2 · Composition for organic optoelectronic device and organic optoelectronic device 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 10,319,921 B2 - Document ID: US10319921B2 - Status: Granted - Kind: B2 - Application number: 15/628,901 - Filed: 2017-06-21 - Published: 2018-01-25 - Granted: 2019-06-11 - Earliest claimed: 2016-07-19 - Assignees: Samsung SDI Co., Ltd. - Applicants: Samsung SDI Co., Ltd. - Inventors: Dong Min Kang; Youngkwon Kim; Changwoo Kim; Eun Sun Yu; Byoungkwan Lee; Hanill Lee; Sung-Hyun Jung; SooYoung Jeong; Ho Kuk Jung - Web page: https://patentgrep.com/patent/US10319921B2 ## CPC - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - C07D 209/82: Carbazoles; Hydrogenated carbazoles - C07D 247/02: having the nitrogen atoms in positions 1 and 3 - C07D 401/14: containing three or more hetero rings - C07D 487/04: Ortho-condensed systems - C07D 493/04: Ortho-condensed systems - C07D 495/04: Ortho-condensed systems - C09K 11/06: containing organic luminescent materials - H05B 33/20: characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded - H10K 50/12: comprising dopants - H10K 50/15: Hole transporting layers - H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)} - H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons} - C09K 2211/1029: containing one nitrogen atom as the heteroatom - C09K 2211/1044: containing two nitrogen atoms as heteroatoms - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 2101/10: Triplet emission - H10K 2101/90: {Multiple hosts in the emissive layer} - H10K 2102/302: {of OLED structures} - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE - H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL ## Abstract Disclosed are a composition for an organic optoelectronic device includes at least one of a first host compound represented by a combination of Chemical Formula 1 and Chemical Formula 2, and at least one of a second host compound represented by a combination of Chemical Formula 3 and Chemical Formula 4, and an organic optoelectronic device including the same, and a display device. Details of Chemical Formula 1 to 4 are the same as described in the detailed description. ## Claims ### Claim 1 A composition for an organic optoelectronic device, the composition comprising: at least one of a first host compound represented by a combination of Chemical Formula 1 and Chemical Formula 2, and at least one of a second host compound represented by a combination of Chemical Formula 3 and Chemical Formula 4: wherein, in Chemical Formulae 1 to 4, two adjacent *'s of Chemical Formula 1 are bound to two adjacent *'s of Chemical Formula 2 and the remainder *'s of Chemical Formula 1 not being bound to *'s of Chemical Formula 2 are CRa, two adjacent *'s of Chemical Formula 3 are bound to two *'s of Chemical Formula 4, the substituent A is a substituted or unsubstituted carbazolyl group, Ar1 and Ar2 are independently a substituted or unsubstituted C6 to C30 aryl group, L1 to L3 are independently a single bond or a substituted or unsubstituted C6 to C30 arylene group, the C6 to C30 arylene group consisting of carbocyclic ring(s), X is O or S, Y1 and Y2 are independently deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolyl group, or a substituted or unsubstituted quinoxalinyl group, the C6 to C30 aryl group consisting of carbocyclic ring(s), at least one of Y1 and Y2 is a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolyl group, or a substituted or unsubstituted quinoxalinyl group, Ra and R1 to R5 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, the C6 to C20 aryl group consisting of carbocyclic ring(s), and the “substituted” refers to replacement of at least one hydrogen by deuterium, a C1 to C4 alkyl group, a C6 to C12 aryl group, or a C2 to C20 heterocyclic group. ### Claim 2 (depends on 1) The composition for an organic optoelectronic device as claimed in claim 1, wherein Chemical Formula 1 is represented by Chemical Formula 1-I or Chemical Formula 1-II: wherein, in Chemical Formulae 1-I and 1-II, two adjacent *'s are bound to two adjacent *'s of Chemical Formula 2 and the remainder *'s not being bound to *'s of Chemical Formula 2 are CRa, L1 is a single bond or a substituted or unsubstituted C6 to C30 arylene group, Ar1 is a substituted or unsubstituted C6 to C30 aryl group, Ar3 is a C6 to C12 aryl group, Ra and R1 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof, and R6 to R11 are independently hydrogen, deuterium, a C1 to C4 alkyl group, a C6 to C12 aryl group, or a C2 to C20 heterocyclic group. ### Claim 3 (depends on 1) The composition for an organic optoelectronic device as claimed in claim 1, wherein the first host compound is represented by one of Chemical Formula C, Chemical Formula E, and Chemical Formula F: wherein, in Chemical Formula C, Chemical Formula E, and Chemical Formula F, the substituent A is a substituted or unsubstituted carbazolyl group, Ar1 and Ar2 are independently substituted or unsubstituted C6 to C20 aryl group, L1 is a single bond or a substituted or unsubstituted C6 to C20 arylene group, and Ra1 to Ra4 and R1 to R3 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof. ### Claim 4 (depends on 3) The composition for an organic optoelectronic device as claimed in claim 3, wherein the first host compound is represented by one of Chemical Formula C1 to Chemical Formula C6, Chemical Formula E1 to Chemical Formula E6, and Chemical Formula F1 to Chemical Formula F6: wherein, in Chemical Formula C1 to Chemical Formula C6, Chemical Formula E1 to Chemical Formula E6, and Chemical Formula F1 to Chemical Formula F6, Ar1 and Ar2 are independently substituted or unsubstituted C6 to C20 aryl group, Ar3 is a C6 to C12 aryl group, L1 is a single bond or a substituted or unsubstituted C6 to C20 arylene group, R1 to R3 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, and R6 to R11 are independently hydrogen, deuterium, a C1 to C4 alkyl group, or a C6 to C12 aryl group. ### Claim 5 (depends on 4) The composition for an organic optoelectronic device as claimed in claim 4, wherein: Ar1 and Ar2 are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted triphenylene group, Ar3 is a phenyl group, a biphenyl group, or a napthyl group, L1 is a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, R1 to R3 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted phenyl group, or a combination thereof, R6 to R11 are independently hydrogen, deuterium, a C1 to C4 alkyl group, or a phenyl group, and the “substituted” refers to replacement of at least one hydrogen by deuterium, a C1 to C4 alkyl group, or a C6 to C12 aryl group. ### Claim 6 (depends on 1) The composition for an organic optoelectronic device as claimed in claim 1, wherein the second host compound is represented by one of Chemical Formula 3-I, Chemical Formula 3-II, Chemical Formula 3-III, and Chemical Formula 3-IV: wherein, in Chemical Formula 3-I, Chemical Formula 3-II, Chemical Formula 3-III, and Chemical Formula 3-IV, X is O or S, L2 and L3 are independently a single bond or a substituted or unsubstituted C6 to C30 arylene group, the C6 to C30 arylene group consisting of carbocyclic ring(s), ET is a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolyl group, or a substituted or unsubstituted quinoxalinyl group, Y1 and Y2 are independently a substituted or unsubstituted C6 to C20 aryl group, the C6 to C20 aryl group consisting of carbocyclic ring(s), and R4 and R5 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, the C6 to C20 aryl group consisting of carbocyclic ring(s). ### Claim 7 (depends on 6) The composition for an organic optoelectronic device as claimed in claim 6, wherein: L2 and L3 are independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted quaterphenylene group, ET is a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, or a substituted or unsubstituted quinazolyl group, Y1 and Y2 are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group, R4 and R5 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted phenyl group, or a combination thereof, and the “substituted” refers to replacement of at least one hydrogen by deuterium, a C1 to C4 alkyl group, or a C6 to C12 aryl group. ### Claim 8 (depends on 1) The composition for an organic optoelectronic device as claimed in claim 1, wherein the first host compound is represented by one of Chemical Formula C2, Chemical Formula C3, Chemical Formula C4, Chemical Formula E1, Chemical Formula E2, Chemical Formula E3, Chemical Formula E4, and Chemical Formula F1; and the second host compound is represented by Chemical Formula 3-I: wherein, in Chemical Formula C2, Chemical Formula C3, Chemical Formula C4, Chemical Formula E1, Chemical Formula E2, Chemical Formula E3, Chemical Formula E4, and Chemical Formula F1, Ar1 and Ar2 are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted triphenylene group, Ar3 is a phenyl group, a biphenyl group, or a naphthyl group, L1 is a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, and R1 to R3 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted phenyl group, or a combination thereof, R6 to R11 are independently hydrogen, deuterium, a C1 to C4 alkyl group, or a phenyl group, wherein, in Chemical Formula 3-I, L2 and L3 are independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted quaterphenylene group, ET is a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, or a substituted or unsubstituted quinazolyl group, Y2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group, R4 and R5 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted phenyl group, or a combination thereof. ### Claim 9 (depends on 1) The composition for an organic optoelectronic device as claimed in claim 1, wherein the composition further includes a phosphorescent dopant. ### Claim 10 (depends on 1) An organic optoelectronic device, comprising an anode and a cathode facing each other, and at least one organic layer disposed between the anode and the cathode, wherein the organic layer includes the composition for an organic optoelectronic device as claimed in claim 1. ### Claim 11 (depends on 10) The organic optoelectronic device as claimed in claim 10, wherein the organic layer includes a light emitting layer, and the composition for an organic optoelectronic device is included as a host of the light emitting layer. ### Claim 12 (depends on 10) A display device comprising the organic optoelectronic device as claimed in claim 10. ### Claim 13 A composition for an organic optoelectronic device, the composition comprising: at least one of a first host compound represented by a combination of Chemical Formula 1 and Chemical Formula 2, and at least one of a second host compound represented by Chemical Formula 3-I, Chemical Formula 3-II, Chemical Formula 3-III, or Chemical Formula 3-IV: wherein, in Chemical Formulae 1 and 2, two adjacent *'s of Chemical Formula 1 are bound to two adjacent *'s of Chemical Formula 2 and the remainder *'s of Chemical Formula 1 not being bound to *'s of Chemical Formula 2 are CRa, the substituent A is a substituted or unsubstituted carbazolyl group, Ar1 and Ar2 are independently a substituted or unsubstituted C6 to C30 aryl group, L1 is a single bond or a substituted or unsubstituted C6 to C30 arylene group, Ra and R1 to R3 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, wherein, in Chemical Formula 3-I, Chemical Formula 3-II, Chemical Formula 3-III, and Chemical Formula 3-IV, X is O or S, L2 and L3 are independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted quaterphenylene group, ET is a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, or a substituted or unsubstituted quinazolyl group, Y1 and Y2 are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group, and R4 and R5 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted phenyl group, or a combination thereof, and the “substituted” refers to replacement of at least one hydrogen by deuterium. a C1 to C4 alkyl group, or a C6 to C12 aryl group.