# US 2023/0057581 A1 · Heterocyclic compound, organic light-emitting diode comprising same, and composition for organic layer of organic light-emitting diode > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2023/0057581 A1 - Document ID: US20230057581A1 - Status: Published application - Kind: A1 - Application number: 17/782,051 - Filed: 2020-12-17 - Published: 2023-02-23 - Earliest claimed: 2019-12-26 - Assignees: Lt Materials Co., Ltd. - Applicants: Lt Materials Co., Ltd. - Inventors: Ji-Yoon BYUN; Jun-Tae MO; Dong-Jun KIM - Web page: https://patentgrep.com/patent/US20230057581A1 ## CPC - C07D 405/04: directly linked by a ring-member-to-ring-member bond - C07D 403/04: directly linked by a ring-member-to-ring-member bond - C07D 405/12: linked by a chain containing hetero atoms as chain links - C07D 405/14: containing three or more hetero rings - C07D 409/04: directly linked by a ring-member-to-ring-member bond - C07D 409/14: containing three or more hetero rings - H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom} - H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom} - H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene} - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene} - H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)} - H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes} - H10K 2101/90: {Multiple hosts in the emissive layer} - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES ## Abstract The present application provides a heterocyclic compound, and an organic light emitting device containing the heterocyclic compound in an organic material layer. ## Claims ### Claim 1 A heterocyclic compound represented by the following Chemical Formula 1: wherein, in Chemical Formula 1, L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; X is O; S; or NRa; Y1 to Y5 are the same as or different from each other, and each independently N or CRb, at least one or more of Y1 to Y5 are N, and when there are two or more CRbs, Rbs are the same as or different from each other; R1 is represented by the following Chemical Formula A; R2 to R9 are hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms; Ra is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Rb is selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heteroring having 2 to 60 carbon atoms; m and n are each independently an integer of 0 to 3, and when m and n are each 2 or greater, substituents in the parentheses are the same as or different from each other; and p is 0 or 1, in Chemical Formula A, L11 and L12 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms; Ar11 and Ar12 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or Ar11 and Ar12 bond to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heteroring having 2 to 60 carbon atoms; a and b are each 0 or 1; and means a position bonding to L1 of Chemical Formula 1. ### Claim 2 (depends on 1) The heterocyclic compound of claim 1, wherein the “substituted or unsubstituted” means being substituted with one or more substituents selected from the group consisting of a linear or branched alkyl group having 1 to 60 carbon atoms; a linear or branched alkenyl group having 2 to 60 carbon atoms; a linear or branched alkynyl group having 2 to 60 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 60 carbon atoms; a monocyclic or polycyclic heterocycloalkyl group having 2 to 60 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 60 carbon atoms; a monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms; a silyl group; a phosphine oxide group; and an amine group, or being unsubstituted, or being substituted with a substituent linking two or more substituents selected from among the substituents illustrated above, or being unsubstituted. ### Claim 3 (depends on 1) The heterocyclic compound of claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 2 or 3: in Chemical Formulae 2 and 3, each substituent has the same definition as in Chemical Formula 1. ### Claim 4 (depends on 3) The heterocyclic compound of claim 3, wherein Chemical Formula 2 is represented by any one of the following Chemical Formulae 2-1 to 2-6: in Chemical Formulae 2-1 to 2-6, L1, L2, X, R1, m and n have the same definitions as in Chemical Formula 1; and Y11 to Y15 are CRb, and Rb has the same definition as in Chemical Formula 1. ### Claim 5 (depends on 3) The heterocyclic compound of claim 3, wherein Chemical Formula 3 is represented by any one of the following Chemical Formulae 3-1 to 3-6: in Chemical Formulae 3-1 to 3-6, L1, L2, X, R1, m and n have the same definition as in Chemical Formula 1, Y11 to Y15 are CRb, and Rb has the same definition as in Chemical Formula 1. ### Claim 6 (depends on 1) The heterocyclic compound of claim 1, wherein Chemical Formula A is represented by any one of the following Chemical Formulae A-1 to A-5: in Chemical Formulae A-1 to A-5, L13 and L14 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms; Ar13 and Ar14 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms; R20 to R26, are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; X11 is O; S; or CRcRd, and Rc and Rd are the same as or different from each other and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; c and d are each 0 or 1; and means a position bonding to L1 of Chemical Formula 1. ### Claim 7 (depends on 1) The heterocyclic compound of claim 1, wherein Chemical Formula 1 is represented by any one of the following compounds: ### Claim 8 (depends on 1) An organic light emitting device comprising: a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers comprise the heterocyclic compound of claim 1. ### Claim 9 (depends on 8) The organic light emitting device of claim 8, wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the heterocyclic compound. ### Claim 10 (depends on 8) The organic light emitting device of claim 8, wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the heterocyclic compound as a host material of a light emitting material. ### Claim 11 (depends on 10) The organic light emitting device of claim 10, wherein the light emitting layer comprises two or more host materials, and at least one of the host materials is the heterocyclic compound. ### Claim 12 (depends on 8) The organic light emitting device of claim 8, further comprising one, two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transfer layer, an electron injection layer, an electron transfer layer, an electron blocking layer, a hole auxiliary layer and a hole blocking layer. ### Claim 13 (depends on 1) A composition for an organic material layer of an organic light emitting device, the composition comprising: the heterocyclic compound represented by Chemical Formula 1 of claim 1; and any one of the following heterocyclic compounds 1-1 to 1-14: ### Claim 14 (depends on 13) The composition for an organic material layer of an organic light emitting device of claim 13, wherein, in the composition, the heterocyclic compound represented by Chemical Formula 1 and any one of the heterocyclic compounds 1-1 to 1-14 have a weight ratio of 1:10 to 10:1.