# US 9,437,826 B2 · Heterocyclic compound 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 9,437,826 B2 - Document ID: US9437826B2 - Status: Granted - Kind: B2 - Application number: 14/167,037 - Filed: 2014-01-29 - Published: 2014-12-18 - Granted: 2016-09-06 - Earliest claimed: 2013-06-18 - Assignees: Samsung Display Co., Ltd.; Pusan National University Industry-University Cooperation Foundation - Applicants: Samsung Display Co., Ltd.; Pusan National University Industry-University Cooperation Foundation - Inventors: Jae-Hong Kim; Myeong-Suk Kim; Soung-Wook Kim; Hong-Suk Suh; Jin-Soo Hwang - Web page: https://patentgrep.com/patent/US9437826B2 ## CPC - H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)} - C07D 409/14: containing three or more hetero rings - H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons} - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 50/15: Hole transporting layers - H10K 50/16: Electron transporting layers - H10K 2101/10: Triplet emission - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) ## Abstract A heterocyclic compound, an organic light-emitting device, and a flat panel display apparatus, the compound being represented by Formula 1, below: ## Claims ### Claim 1 A heterocyclic compound represented by Formula 1, below: wherein, R1 to R17 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C2 to C60 alkenyl group, a substituted or unsubstituted C2 to C60 alkynyl group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C6 to C60 aryloxy group, a substituted or unsubstituted C6 to C60 arylthio group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, a substituted or unsubstituted C6 to C60 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group, and wherein a, b, c, d, m, and n are each independently 0 or 1, one of a, b, c, or d being 0, and one of m or n being 0. ### Claim 2 (depends on 1) The heterocyclic compound as claimed in claim 1, wherein the heterocyclic compound represented by Formula 1 is represented by Formula 2, below: wherein R1 to R15, and R17 in Formula 2 are the same as defined with respect to Formula 1, and wherein a, b, c, and d are each independently 0 or 1, one of a, b, c, or d being 0. ### Claim 3 (depends on 1) The heterocyclic compound as claimed in claim 1, wherein the heterocyclic compound represented by Formula 1 is represented by Formula 3, below: wherein R1 to R9, and R11 to R17 in Formula 3 are the same as defined with respect to Formula 1, and wherein m and n are each independently 0 or 1, one of m or n being 0. ### Claim 4 (depends on 1) The heterocyclic compound as claimed in claim 1, wherein the heterocyclic compound represented by Formula 1 is represented by Formula 4, below: wherein R1 to R9, R11 to R15, and R17 in Formula 4 are the same as defined with respect to Formula 1. ### Claim 5 (depends on 1) The heterocyclic compound as claimed in claim 1, wherein R1, R3, R4, R7, R13, and R15 in Formula 1 are each independently a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, or a substituted or unsubstituted C6 to C60 condensed polycyclic group. ### Claim 6 (depends on 1) The heterocyclic compound as claimed in claim 1, wherein R1, R3, R4, R7, R13, and R15 in Formula 1 are any one of Formulae 2a to 2d, below: wherein, in Formulae 2a to 2d: Z1 and Z2 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C20 heteroaryl group, a substituted or unsubstituted C6 to C20 condensed polycyclic group, a halogen group, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group; p is an integer of 1 to 7; and * indicates a binding site. ### Claim 7 (depends on 1) The heterocyclic compound as claimed in claim 1, wherein R2, R5, R6, R8 to R12, R14, R16, and R17 are each independently a hydrogen atom or a deuterium atom. ### Claim 8 (depends on 1) The heterocyclic compound as claimed in claim 1, wherein the compound represented by Formula 1 is any one of compounds 1-33, below: ### Claim 9 (depends on 1) An organic light-emitting diode, comprising: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer includes the heterocyclic compound as claimed in claim 1. ### Claim 10 (depends on 9) The organic light-emitting device as claimed in claim 9, wherein the organic layer includes a hole injection layer, a hole transport layer, a functional layer having a hole injection capability and a hole transportation capability, an emission layer, an electron injection layer, an electron transport layer, or a functional layer having an electron injection capability and an electron transportation capability. ### Claim 11 (depends on 9) The organic light-emitting device as claimed in claim 9, wherein the organic layer is an emission layer, an electron transport layer, or a hole transport layer. ### Claim 12 (depends on 9) The organic light-emitting device as claimed in claim 9, wherein: the organic layer includes an emission layer, and a hole injection layer, a hole transport layer, or a functional layer having a hole injection capability and a hole transportation capability, and the emission layer includes a red layer, a green layer, a blue layer, and a white layer, one of which includes a phosphorescent compound. ### Claim 13 (depends on 12) The organic light-emitting device as claimed in claim 12, wherein the hole injection layer, the hole transport layer, or the functional layer having a hole injection capability and a hole transportation capability includes a charge-generation material. ### Claim 14 (depends on 13) The organic light-emitting device as claimed in claim 13, wherein the charge-generation material is a p-dopant. ### Claim 15 (depends on 14) The organic light-emitting device as claimed in claim 14, wherein the p-dopant is a quinone derivative, metal oxide, or a cyano group-containing compound. ### Claim 16 (depends on 9) The organic light-emitting device as claimed in claim 9, wherein the organic layer includes an electron transport layer, the electron transport layer including a metal-containing material. ### Claim 17 (depends on 16) The organic light-emitting device as claimed in claim 16, wherein the metal-containing material is a Li complex. ### Claim 18 (depends on 16) The organic light-emitting device as claimed in claim 16, wherein the metal-containing material includes one of lithium quinolate (LiQ) or Compound 203 below: ### Claim 19 (depends on 9) The organic light-emitting device as claimed in claim 9, wherein the organic layer is formed by using a wet process performed by using the heterocyclic compound. ### Claim 20 (depends on 9) A flat panel display apparatus, comprising the organic light-emitting device as claimed in claim 9, wherein the first electrode of the organic light-emitting device is electrically connected to a source electrode or a drain electrode of a thin film transistor.