# US 12,120,949 B2 · 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 12,120,949 B2 - Document ID: US12120949B2 - Status: Granted - Kind: B2 - Application number: 17/269,331 - Filed: 2019-11-27 - Published: 2021-09-16 - Granted: 2024-10-15 - Earliest claimed: 2018-11-27 - Assignees: LG Chem, Ltd. - Applicants: LG Chem, Ltd. - Inventors: Miyeon Han; Sung Kil Hong; Jungoh Huh; Dong Uk Heo; Jae Tak Lee; Junghoon Yang - Web page: https://patentgrep.com/patent/US12120949B2 ## CPC - H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene} - H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene - H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene} - H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)} - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - 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} - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 50/165: comprising dopants - H10K 50/171: {Electron injection layers} - H10K 2101/10: Triplet emission - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES ## Abstract Provided is an organic light emitting device including a first organic material layer that comprises a compound of Formula 1: and a second organic material layer comprising a compound of Formula 2: ## Claims ### Claim 1 An organic light emitting device, comprising: a positive electrode; a negative electrode; and a first organic material layer and a second organic material layer provided between the positive electrode and the negative electrode, wherein the first organic material layer comprises a compound of the following Formula 1, and the second organic material layer comprises a compound of the following Formula 2: wherein in Formula 1: L101 and L102 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; R11 to R18 are deuterium, or adjacent substituents are bonded to each other to form a ring substituted with deuterium; Ar101 and Ar102 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, or are linked to an adjacent substituent to form a substituted or unsubstituted ring; m1 and m2 are each an integer from 0 to 5; when m1 is 2 or higher, the L101s are the same as or different from each other, and when m2 is 2 or higher, the L102s are the same as or different from each other, and the compound of Formula 1 is at least 40% or more deuterated; wherein in Formula 2: Y is O or S; R21 to R24 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are the following Formula 3, or adjacent substituents are bonded to each other to form a substituted or unsubstituted ring; at least one of R21 and R22 is the following Formula 3; r21 to r24 are the same as or different from each other, and are each independently an integer from 0 to 4, and when r21 is 2 or higher, the R21s are the same as or different from each other, and when r22 is 2 or higher, the R22s are the same as or different from each other, and when r23 is 2 or higher, the R23s are the same as or different from each other, and when r24 is 2 or higher, the R24s are the same as or different from each other; wherein in Formula 3: X1 is N or C(R31), X2 is N or C(R32), X3 is N or C(R33), and one or more of X1 to X3 are N; R31, R32, and R33 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are bonded to Ar1 or Ar2 to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted hetero ring; Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group which is unsubstituted or substituted with R41, or a heterocyclic group which is unsubstituted or substituted with R42, or are bonded to R31, R32, or R33 to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted hetero ring; R41 and R42 are the same as or different from each other, and are each independently one selected from the group consisting of deuterium, a halogen group, a nitrile group, an alkyl group, a haloalkyl group, an alkoxy group, a silyl group, an aryl group, and a heterocyclic group, or a group to which two or more substituents are linked; L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group; m is an integer from 0 to 4, and when m is 2 or higher, the Ls are the same as or different from each other; and * is a moiety bonded to Formula 2. ### Claim 2 (depends on 1) The organic light emitting device of claim 1, wherein Formula 3 is any one of the following Formulae 301 to 303: wherein in Formulae 301 to 303: the definitions of L, m, Ar1, and Ar2 are the same as those defined in Formula 3; one or more of X1 to X3 are N, and the others are CH or CD; R30 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; and r30 is an integer from 0 to 4, and when r30 is 2 or higher, the R30s are the same as or different from each other. ### Claim 3 (depends on 1) The organic light emitting device of claim 1, wherein Formula 2 is any one of the following Formulae 201, 203, and 204: wherein in Formulae 201, 203, and 204: the definitions of X1 to X3, L, m, Ar1, Ar2, R21 to R24, r21 to r24, and Y are the same as those defined in Formula 2; X4 is N or C(R34), X5 is N or C(R35), X6 is N or C(R36), and one or more of X4 to X6 are N; R34, R35, and R36 are the same as or different from each other, and are each independently hydrogen or deuterium, or are bonded to Ar3 or Ar4 to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted hetero ring; Ar3 and Ar4 are the same as or different from each other, and are each independently an aryl group which is unsubstituted or substituted with R43, or a heterocyclic group which is unsubstituted or substituted with R44, or are bonded to R34, R35, or R36 to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted hetero ring; R43 and R44 are the same as or different from each other, and are each independently one selected from the group consisting of deuterium, a halogen group, a nitrile group, an alkyl group, a haloalkyl group, an alkoxy group, a silyl group, an aryl group, and a heterocyclic group, or a group to which two or more substituents are linked; L11 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group; m11 is an integer from 0 to 4, and when m11 is 2 or higher, the L11s are the same as or different from each other. ### Claim 4 (depends on 1) The organic light emitting device of claim 1, wherein Formula 2 is any one of the following Formulae 211 to 214: wherein in Formulae 211 to 214: the definitions of X1 to X3, L, m, Ar1, Ar2, R21 to R24, r21 to r24, and Y are the same as those defined in Formula 2. ### Claim 5 (depends on 1) The organic light emitting device of claim 1, wherein Formula 2 is any one of the following Formulae 401 to 403: wherein in Formulae 401 to 403: the definitions of X1 to X3, L, m, Ar1, Ar2, R23, R24, r23, r24, and Y are the same as those defined in Formula 2; R25 to R28 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and r25 and r28 are each an integer from 0 to 6, r26 is an integer from 0 to 5, r27 is an integer from 0 to 3, r28 and r26 are the same as or different from each other, and are each independently an integer from 0 to 6, and when r25 is 2 or higher, the R25s are the same as or different from each other, and when r26 is 2 or higher, the R26s are the same as or different from each other, and when r27 is 2 or higher, the R27s are the same as or different from each other, and when r28 is 2 or higher, the R28s are the same as or different from each other. ### Claim 6 (depends on 1) The organic light emitting device of claim 1, wherein the compound of Formula 1 is 60% or more deuterated. ### Claim 7 (depends on 1) The organic light emitting device of claim 1, wherein one of Ar101 and Ar102 is a substituted or unsubstituted C2-C20 heteroaryl group, and the other is a substituted or unsubstituted C6-C20 aryl group. ### Claim 8 (depends on 1) The organic light emitting device of claim 1, wherein the compound of Formula 1 is any one compound selected from the following Compounds M1 to M5 and M7 to M34: wherein in Compound M1, z is 8 and a value of x+y+z+n is 20 to 26; wherein in Compound M2, z is 8 and a value of x+y+z+p+n is 24 to 30; wherein in Compound M3, z is 8 and a value of x+y+z+p+n+r is 26 to 32; wherein in Compound M4, z is 8 and a value of x+y+z+q+n is 22 to 30; wherein in Compound M5, z is 8 and a value of x+y+z+p+n+q is 28 to 34; wherein in Compound M7, z is 8 and a value of x+y+z+p+n is 22 to 28; wherein in Compound M8, y is 8 and a value of x+y+z is 16 to 22; wherein in Compound M9, y is 8 and a value of x+y+z+n is 20 to 26; wherein in Compound M10, z is 8 and a value of x+y+z+p+n is 22 to 28; wherein in Compound M11, z is 8 and a value of x+y+z+n is 20 to 26; wherein in Compound M1, y is 8 and a value of x+y+z is 18 to 24; wherein in Compound M13, z is 8 and a value of x+y+z+p+n is 21 to 27; wherein in Compound M14, z is 8 and a value of x+y+2+n is 16 to 22; wherein in Compound M15, y is 8 and a value of x+y+z+n is 20 to 26; wherein in Compound M16, z is 7, y is 3, and a value of x+y+z+p is 14 to 20; wherein in Compound M17, z is 8 and a value of x+y+z+p is 19 to 25; wherein in Compound M18, y is 8 and a value of x+y+z+n is 19 to 25; wherein in Compound M19, z is 8 and a value of x+y+z+p+n is 20 to 26; wherein in Compound M20, y is 8 and a value of x+y+z is 14 to 20; wherein in Compound M21, y is 8 and a value of x+y+z is 14 to 20; wherein in Compound M22, y is 8 and a value of x+y+z is 14 to 20; wherein in Compound M23, y is 8 and a value of x+y+z is 14 to 20; wherein in Compound M24, z is 8 and a value of x+y+z+n is 18 to 24; wherein in Compound M25, z is 8 and a value of x+y+z+p is 16 to 22; wherein in Compound M26, z is 8 and a value of x+y+2+n is 12 to 24; wherein in Compound M27, y is 8 and a value of x+y+z+n is 13 to 26; wherein in Compound M28, y is 8 and a value of x+y+z+n is 16 to 22; wherein in Compound M29, z is 8 and a value of x+y+z+n is 12 to 24; wherein in Compound M30, y is 8 and a value of x+y+z is 12 to 24; wherein in Compound M31, y is 8 and a value of x+y+z is 11 to 22; wherein in Compound M32, y is 8 and a value of x+y+z is 11 to 22; wherein in Compound M33, z is 8 and a value of x+y+z+p+n is 15 to 30; wherein in Compound M34, y is 8 and a value of x+y+z is 11 to 22. ### Claim 9 (depends on 1) The organic light emitting device of claim 1, wherein the compound of Formula 1 is any one compound selected from the following compounds: ### Claim 10 (depends on 1) The organic light emitting device of claim 1, wherein the compound of Formula 2 is any one compound selected from the following compounds: ### Claim 11 (depends on 1) The organic light emitting device of claim 1, wherein the first organic material layer is a light emitting layer. ### Claim 12 (depends on 1) The organic light emitting device of claim 1, wherein the first organic material layer is a light emitting layer, the light emitting layer comprises a host material, and the host material comprises the compound of Formula 1. ### Claim 13 (depends on 11) The organic light emitting device of claim 11, wherein the organic light emitting device further comprises one or more additional light emitting layers. ### Claim 14 (depends on 11) The organic light emitting device of claim 11, wherein the organic light emitting device further comprises one or more additional light emitting layers in which the maximum light emission peak appears in a wavelength band different from a wavelength band in which the maximum light emission peak of the light emitting layer comprising one or more of the compound of Formula 1 appears. ### Claim 15 (depends on 11) The organic light emitting device of claim 11, wherein the light emitting layer comprising the compound of Formula 1 further comprises a fluorescent dopant. ### Claim 16 (depends on 14) The organic light emitting device of claim 14, wherein one or more light emitting layers in which the maximum light emission peak appears in a wavelength band different from a wavelength band in which the maximum light emission peak of the light emitting layer comprising one or more of the compound of Formula 1 appears comprise a phosphorescent dopant. ### Claim 17 (depends on 1) The organic light emitting device of claim 1, wherein Ar101 and Ar102 are the same as or different from each other, and are each 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, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted naphthobenzofuran group, a substituted or unsubstituted naphthobenzothiophene group, a substituted or unsubstituted benzocarbazole group, a substituted or unsubstituted indole group, a substituted or unsubstituted furan group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted quinoline group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, or a substituted or unsubstituted triazine group.