# US 12,016,243 B2 · Condensed cyclic 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 12,016,243 B2 - Document ID: US12016243B2 - Status: Granted - Kind: B2 - Application number: 17/271,762 - Filed: 2019-10-02 - Published: 2021-10-28 - Granted: 2024-06-18 - Earliest claimed: 2018-12-14 - Assignees: LG Chem, Ltd. - Applicants: LG Chem, Ltd. - Inventors: Jungoh Huh; Sung Kil Hong; Sangbin Lee - Web page: https://patentgrep.com/patent/US12016243B2 ## CPC - C09K 11/06: containing organic luminescent materials - C07D 405/04: directly linked by a ring-member-to-ring-member bond - C07D 405/10: linked by a carbon chain containing aromatic rings - C07D 405/14: containing three or more hetero rings - C07D 409/04: directly linked by a ring-member-to-ring-member bond - H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene} - H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-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 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene} - C09K 2211/1018: Heterocyclic compounds - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 50/131: {with spacer layers between the electroluminescent layers} - H10K 50/15: Hole transporting layers - H10K 50/16: Electron transporting layers - H10K 50/165: comprising dopants - H10K 50/17: Carrier injection layers - H10K 50/171: {Electron injection layers} - H10K 50/19: Tandem OLEDs - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES ## Abstract Provided is a compound of Chemical Formula 1: wherein: X is O or S; one or more of R9 to R16 are linked to * of the following Chemical Formula 2; and R1 to R8, and the rest of R9 to R16 not linked to Chemical Formula 2, are the same as or different from each other, and each independently is hydrogen, deuterium, a cyano group, a nitro group, a carbonyl group, or a substituted or unsubstituted: silyl group, boron group, alkyl group, alkoxy group, aryloxy group, cycloalkyl group, aryl group or heterocyclic group, or bond to adjacent groups to form a substituted or unsubstituted benzene ring; and an organic light emitting device including the same. ## Claims ### Claim 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 at least one of the one or more organic material layers includes a hole injection layer, a hole transfer layer, or a layer carrying out hole transfer and hole injection at the same time, and the hole injection layer, the hole transfer layer, or the layer carrying out hole transfer and hole injection at the same time includes a compound of Chemical Formula 1: wherein, in Chemical Formula 1: X is O or S; one or more of R9 to R16 are linked to * of the following Chemical Formula 2; and R1 to R8, and the rest of R9 to R16 not linked to Chemical Formula 2, are the same as or different from each other, and each independently is hydrogen, deuterium, a cyano group, a nitro group, a carbonyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; wherein in Chemical Formula 2: A1 to A3 are the same as or different from each other and each independently is N or CR, and one or more of Al to A3 are N; L1 and L2 are the same as or different from each other, and each independently is a direct bond, a substituted or unsubstituted cycloalkylene group, or a substituted or unsubstituted arylene group; L3 is a direct bond, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted naphthylene group; one or more of Ar1 and Ar2 are a substituted or unsubstituted dicyclic or higher condensed aryl group, and the rest are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group; Rs are the same as or different from each other, and each independently is hydrogen, deuterium, a cyano group, a nitro group, a carbonyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and m1 to m3 are each an integer of 0 to 3, and when m1 to m3 are each 2 or greater, two or more substituents in the parentheses are the same as or different from each other. ### Claim 2 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 the one or more organic material layers include one or more light emitting layers, at least one of the one or more light emitting layers includes a host and a dopant, and the dopant is a blue fluorescent dopant having a maximum light emission wavelength of 400 nm to 520 nm, and wherein one or more layers of the organic material layers includes a compound of Chemical Formula 1: wherein, in Chemical Formula 1: X is O or S; one or more of R9 to R16 are linked to * of the following Chemical Formula 2; and R1 to R8, and the rest of R9 to R16 not linked to Chemical Formula 2, are the same as or different from each other, and each independently is hydrogen, deuterium, a cyano group, a nitro group, a carbonyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; wherein in Chemical Formula 2: A1 to A3 are the same as or different from each other and each independently is N or CR, and one or more of Al to A3 are N; L1 and L2 are the same as or different from each other, and each independently is a direct bond, a substituted or unsubstituted cycloalkylene group, or a substituted or unsubstituted arylene group; L3 is a direct bond, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted naphthylene group; one or more of Ar1 and Ar2 are a substituted or unsubstituted dicyclic or higher condensed aryl group, and the rest are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group; Rs are the same as or different from each other, and each independently is hydrogen, deuterium, a cyano group, a nitro group, a carbonyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and m1 to m3 are each an integer of 0 to 3, and when m1 to m3 are each 2 or greater, two or more substituents in the parentheses are the same as or different from each other. ### Claim 3 (depends on 2) The organic light emitting device of claim 2, wherein the one or more organic material layers include two or more light emitting layers. ### Claim 4 (depends on 2) The organic light emitting device of claim 2, wherein the one or more organic material layers include: a first stack including one or more light emitting layers; and a second stack including one or more light emitting layers; and one or more charge generating layers between the first stack and the second stack, wherein at least one of the first stack or the second stack includes the light emitting layer including the host and the blue fluorescent dopant having a maximum light emission wavelength of 400 nm to 520 nm. ### Claim 5 (depends on 2) The organic light emitting device of claim 2, wherein the one or more organic material layers include: a first stack including one or more light emitting layers; a second stack including one or more light emitting layers; a third stack including one or more light emitting layers; and one or more charge generating layers between each of the first stack and the second stack, and the second stack and the third stack, wherein at least one of the first stack, the second stack, or the third stack includes the light emitting layer including the host and the blue fluorescent dopant having a maximum light emission wavelength of 400 nm to 520 nm. ### Claim 6 (depends on 2) The organic light emitting device of claim 2, wherein two or more of A1 to A3 are N, and the rest is CR, and R has the same definition as in Chemical Formula 2. ### Claim 7 (depends on 2) The organic light emitting device of claim 2, wherein one or more of Ar1 and Ar2 are a substituted or unsubstituted spirofluorenexanthene group, a substituted or unsubstituted spirofluorenethioxanthene group, a substituted or unsubstituted dibenzofuran group, or any one of the following structures, and the rest are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group: wherein in the structures: R21 to R30 are the same as or different from each other, and each independently is hydrogen, deuterium, a cyano group, a nitro group, a carbonyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; n1 is an integer of 0 to 7, n2 is an integer of 0 to 9, n3 and n6 are each an integer of 0 to 6, n4, n5 and n9 are each an integer of 0 to 3, n7 is an integer of 0 to 4, n8 is an integer of 0 to 5, n10 is an integer of 0 to 8, and when n1 to n10 are each 2 or greater, two or more substituents in the parentheses are the same as or different from each other; and * means a linked site. ### Claim 8 (depends on 2) The organic light emitting device of claim 2, wherein Chemical Formula 1 is any one of the following Chemical Formulae 3 to 8: wherein in Chemical Formulae 3 to 8: X, R1 to R8, A1 to A3, L1 to L3 and m1 to m3 have the same definitions as in Chemical Formula 1; Ar3 is a substituted or unsubstituted dicyclic or higher condensed aryl group, a substituted or unsubstituted monocyclic aryl group, or a substituted or unsubstituted heterocyclic group; R21 to R30 are the same as or different from each other, and each independently is hydrogen, deuterium, a cyano group, a nitro group, a carbonyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; R32 is hydrogen, deuterium, a cyano group, a nitro group, a carbonyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; n1 is an integer of 0 to 7, n2 is an integer of 0 to 9, n3 and n6 are each an integer of 0 to 6, n4, n5 and n9 are each an integer of 0 to 3, n7 is an integer of 0 to 4, n8 is an integer of 0 to 5, n10 is an integer of 0 to 8, and when n1 to n10 are each 2 or greater, two or more substituents in the parentheses are the same as or different from each other; and p1 is an integer of 0 to 7, and when p1 is 2 or greater, two or more R32s are the same as or different from each other. ### Claim 9 (depends on 2) The organic light emitting device of claim 2, wherein the compound of Chemical Formula 1 is any one compound selected from among the following compounds: ### Claim 10 (depends on 2) The organic light emitting device of claim 2, wherein the compound of Chemical Formula 1 satisfies the following Equation 1: ΔESTCEl>ΔESTEl wherein in Equation 1: ΔESTCEl is a difference between a singlet energy (S1) value and a triplet energy (T1) value of the compound of Chemical Formula 1; and ΔESTEl is a difference between a singlet energy (S1) value and a triplet energy (T1) value of a compound having the same core structure as the compound of Chemical Formula 1 in which the dicyclic or higher condensed aryl group of Ar1 and/or Ar2 in the compound of Chemical Formula 1 is replaced with a phenyl group. ### Claim 11 (depends on 2) The organic light emitting device of claim 2, wherein the compound of Chemical Formula 1 satisfies the following Equation 2: 0.30 eV<ΔESTCEl<1.5 eV wherein in Equation 2: ΔESTCEl is a difference between a singlet energy (S1) value and a triplet energy (T1) value of the compound of Chemical Formula 1. ### Claim 12 (depends on 2) The organic light emitting device of claim 2, wherein the compound of Chemical Formula 1 satisfies the following Equation 3: ΔESTCEl−ΔESTEl>0.05 eV wherein in Equation 3: ΔESTCEl is a difference between a singlet energy (S1) value and a triplet energy (T1) value of the compound of Chemical Formula 1; and ΔESTEl is a difference between a singlet energy (S1) value and a triplet energy (T1) value of a compound having the same core structure as the compound of Chemical Formula 1 in which the dicyclic or higher condensed aryl group of Ar1 and/or Ar2 in the compound of Chemical Formula 1 is replaced with a phenyl group.