# US 12,006,335 B2 · Heterocyclic compound and organic light emitting device comprising same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,006,335 B2 - Document ID: US12006335B2 - Status: Granted - Kind: B2 - Application number: 17/293,340 - Filed: 2020-01-14 - Published: 2021-12-30 - Granted: 2024-06-11 - Earliest claimed: 2019-03-08 - Assignees: LG Chem, Ltd. - Applicants: LG Chem, Ltd. - Inventors: Kyunghee Kim; Tae Yoon Park; Wanpyo Hong; Sujeong Geum; Jongsoo Song - Web page: https://patentgrep.com/patent/US12006335B2 ## CPC - C07F 5/02: Boron compounds - C07F 5/027: {Organoboranes and organoborohydrides} - C07F 7/0812: {comprising a heterocyclic ring} - C09K 11/06: containing organic luminescent materials - H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene - 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 50/171: {Electron injection layers} - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES ## Abstract A compound represented by Formula 1 and an organic light emitting device including the same, and the compound providing lower driving voltage, improved light efficiency, and improved service life characteristics of the organic light emitting device. ## Claims ### Claim 1 A compound of Formula 1: wherein, in Formula 1: L1 to L5 are the same as or different from each other, and are each independently a substituted or unsubstituted alkylene group, Ar1 to Ar5 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; R1 to R3 and R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted arylheteroarylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; R4 is hydrogen; deuterium; an alkyl group having 1 to 6 carbon atoms, which is unsubstituted or substituted with deuterium; or an arylamine group having 6 to 40 carbon atoms, which is unsubstituted or substituted with a substituent selected from the group consisting of deuterium, an alkyl group having 1 to 6 carbon atoms, a trialkylsilyl group having 3 to 30 carbon atoms, and a triarylsilyl group having 6 to 50 carbon atoms; r1, r2, n1, and n2 are the same as or different from each other, and are each independently an integer from 0 to 4; r4 is an integer from 0 to 3; n4 is 0; r3, r5, n3, and n5 are the same as or different from each other, and are each independently an integer from 0 to 5; m is 0 or 1, and when m is 0, L5 is directly linked to N; a value of n1+n2+n3+n5 is an integer from 1 to 21; a value of r1+n1 is an integer from 0 to 4, a value of r2+n2 is an integer from 0 to 4, a value of r3+n3 is an integer from 0 to 5, a value of r4+n4 is an integer from 0 to 3, and a value of r5+n5 is an integer from 0 to 5; and substituents in the parenthesis are the same as or different from each other, provided that r1 to r5, n1 to n3, and n5 is 2 or higher. ### Claim 2 (depends on 1) The compound of claim 1, wherein the compound of Formula 1 is represented by the following Formula 2 or 3: wherein, in Formulae 2 and 3, L1 to L5, Ar1 to Ar5, R1 to R5, r1 to r5, and n1 to n5 are the same as defined in Formula 1. ### Claim 3 (depends on 1) The compound of claim 1, wherein the compound of Formula 1 is represented by any one of the following Formulae 401 to 407: wherein, in Formulae 401 to 407, L1, L2, L3, L5, Ar1, Ar2, Ar3, Ar5, R1 to R5, r1 to r5, n1, n2, n3, and n5 are the same as defined in Formula 1. ### Claim 4 (depends on 1) The compound of claim 1, wherein L1 to L5 are the same as or different from each other, and are each independently a methylene group which is unsubstituted or substituted with an alkyl group or an aryl group. ### Claim 5 (depends on 1) The compound of claim 1, wherein Ar1 to Ar5 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; or a substituted or unsubstituted biphenyl group. ### Claim 6 (depends on 1) The compound of claim 1, wherein R1 to R5 are the same as or different from each other, and are each independently hydrogen; deuterium; a nitrile group; an alkyl group having 1 to 6 carbon atoms, which is unsubstituted or substituted with deuterium; a cycloalkyl group having 3 to 20 carbon atoms; an aryl group having 6 to 20 carbon atoms, which is unsubstituted or substituted with a substituent selected from the group consisting of deuterium and an alkyl group having 1 to 6 carbon atoms or a substituent formed by linking two or more groups thereof; or an arylamine group having 6 to 40 carbon atoms, which is unsubstituted or substituted with a substituent selected from the group consisting of deuterium, an alkyl group having 1 to 6 carbon atoms, a trialkylsilyl group having 3 to 30 carbon atoms, and a triarylsilyl group having 6 to 50 carbon atoms, or a substituent formed by linking two or more groups thereof. ### Claim 7 (depends on 1) The compound of claim 1, wherein n1 to n3 and n5 are the same as or different from each other, and are each independently 0 or 1. ### Claim 8 (depends on 1) The compound of claim 1, wherein the compound represented by Formula 1 is any one selected from the following compounds: ### Claim 9 (depends on 1) An organic light emitting device comprising: a first electrode; a second electrode provided to face the first electrode; and an organic material layer having one or more layers provided between the first electrode and the second electrode, wherein the one or more layers of the organic material layer comprise the compound of claim 1. ### Claim 10 (depends on 9) The organic light emitting device of claim 9, wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the compound. ### Claim 11 (depends on 9) The organic light emitting device of claim 9, wherein the organic material layer comprises a light emitting layer, the light emitting layer comprises a dopant material, and the dopant material is the compound. ### Claim 12 (depends on 9) The organic light emitting device of claim 9, wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the compound and a compound represented by the following Formula H: wherein, in Formula H, L21 to L23 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, R21 to R27 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, Ar21 to Ar23 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and a is 0 or 1. ### Claim 13 An organic light emitting device comprising: a first electrode; a second electrode provided to face the first electrode; and an organic material layer having one or more layers provided between the first electrode and the second electrode, wherein the organic material layer comprises a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises a compound of Formula 1: wherein, in Formula 1: L1 to L5 are the same as or different from each other, and are each independently a substituted or unsubstituted alkylene group; Ar1 to Ar5 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted arylheteroarylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; r1, r2, n1, and n2 are the same as or different from each other, and are each independently an integer from 0 to 4; r4 is an integer from 0 to 3; n4 is 0; r3, r5, n3, and n5 are the same as or different from each other, and are each independently an integer from 0 to 5; m is 0 or 1, and L5 is directly linked to N, provided that m is 0; a value of n1+2+n3+n4+n5 is an integer from 1 to 21; a value of r1+n1 is an integer from 0 to 4, a value of r2+n2 is an integer from 0 to 4, a value of r3+n3 is an integer from 0 to 5, a value of r4+n4 is an integer from 0 to 3, and a value of r5+n5 is an integer from 0 to 5; and substituents in the parenthesis are the same as or different from each other, provided that r1 to r5, n1 to n3, and n5 is 2 or higher. ### Claim 14 An organic light emitting device comprising: a first electrode; a second electrode provided to face the first electrode; and an organic material layer having one or more layers provided between the first electrode and the second electrode, wherein the organic material layer comprises an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer comprises a compound of Formula 1: wherein, in Formula 1: L1 to L5 are the same as or different from each other, and are each independently a substituted or unsubstituted alkylene group; Ar1 to Ar5 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted arylheteroarylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; r1, r2, n1, and n2 are the same as or different from each other, and are each independently an integer from 0 to 4; r4 is an integer from 0 to 3; n4 is 0; r3, r5, n3, and n5 are the same as or different from each other, and are each independently an integer from 0 to 5; m is 0 or 1, and L5 is directly linked to N, provided that m is 0; a value of n1+n2+n3+n4+n5 is an integer from 1 to 21; a value of r1+n1 is an integer from 0 to 4, a value of r2+n2 is an integer from 0 to 4, a value of r3+n3 is an integer from 0 to 5, a value of r4+n4 is an integer from 0 to 3, and a value of r5+n5 is an integer from 0 to 5; and substituents in the parenthesis are the same as or different from each other, provided that r1 to r5, n1 to n3, and n5 is 2 or higher. ### Claim 15 (depends on 9) The organic light emitting device of claim 9, wherein the organic material layer further comprises one or two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.