# US 12,595,257 B2 · Heterocyclic compound, organic light emitting device including the same and composition for organic layer of organic light emitting device

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- Number: US 12,595,257 B2
- Document ID: US12595257B2
- Status: Granted
- Kind: B2
- Application number: 17/720,608
- Filed: 2022-04-14
- Published: 2023-04-06
- Granted: 2026-04-07
- Earliest claimed: 2021-04-16
- Assignees: LG Display Co., Ltd.; Lt Materials Co., Ltd.
- Applicants: LG Display Co., Ltd.; LT Materials Co., Ltd.
- Inventors: Sang-Beom Kim; Young-Jun Yu; Seon-Keun Yoo; Seung-Kwang Roh; Woo-Chul Choi; Ji-Ho Baek; Kyung-Hoon Lee; Ki-Min Lim; Dong-Jun Kim; Young-Seok No; Hyun-Joo Lee; Eui-Jeong Choi
- Web page: https://patentgrep.com/patent/US12595257B2

## CPC

- C07D 405/14: containing three or more hetero rings
- C07D 409/14: containing three or more hetero rings
- C07D 487/04: Ortho-condensed systems
- C07D 495/04: Ortho-condensed systems
- C09K 11/06: containing organic luminescent materials
- H10K 85/342: {comprising iridium}
- H10K 85/624: {containing six or more rings}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- 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 50/13: comprising stacked EL layers within one EL unit
- H10K 50/18: Carrier blocking layers
- H10K 50/181: {Electron blocking layers}
- H10K 50/19: Tandem OLEDs
- H10K 59/32: Stacked devices having two or more layers, each emitting at different wavelengths
- H10K 2101/10: Triplet emission
- H10K 2101/90: {Multiple hosts in the emissive layer}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

The present disclosure relates to a heterocyclic compound being represented by Formula, an organic light emitting device including the heterocyclic compound and an organic light emitting display device including the organic light emitting device. The organic heterocyclic is included in an organic material layer of the organic light emitting device.

## Claims

### Claim 1

An organic light emitting device, comprising:
a first electrode;
a second electrode facing the first electrode;
a first emitting material layer between the first and second electrodes; and
a first electron blocking layer between the first emitting material layer and the first electrode,
wherein one or more of the at least one organic material layer includes a first compound and a second compound,
wherein the first compound is represented by Formula 1:
wherein N-Het is substituted or unsubstituted and a monocyclic or polycyclic C2 to C60 heterocyclic group having at least one nitrogen atom,
wherein L is a direct bond, a substituted or unsubstituted C6 to C60 arylene group or a substituted or unsubstituted C2 to C60 heteroarylene group, and a is an integer of 1 to 3, wherein when a is 2 or more, two or more L are same or different,
wherein R1 to R12 are same or different, wherein each of R1 to R12 is independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; 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 C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; —P(═O)RR′; —SiRR′R″; and —NRR′, or adjacent two or more of R1 to R12 are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring, wherein b is an integer of 1 to 3, wherein when b is 2 or more, two or more R9 are the same as or different,
wherein R, R′ and R″ are the same or different, wherein each of R, R′ and R″ is independently selected from the group consisting of a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 a heteroaryl group,
wherein a deuteration ratio of the heterocyclic compound is 20% to 100%,
wherein the second compound is represented by Formula 2:
wherein Ra and Rb are same or different, and each of Ra and Rb is independently a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group,
wherein Ra1 to Ra14 are same or different, and wherein each of Ra1 to Ra14 is independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group and a substituted or unsubstituted C2 to C60 heteroaryl group, or adjacent two or more of Ra1 to Ra14 are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring,
wherein the electron blocking layer includes a first electron blocking material represented by Formula 10:
wherein each of R51 and R52 is independently a substituted or unsubstituted C1 to C10 alkyl, or adjacent two of R51 and R52 is connected to form a ring, wherein b1 is an integer of 0 to 4, and b2 is an integer of 0 to 5,
wherein each of R53 and R54 is independently a substituted or unsubstituted C1 to C10 alkyl, or adjacent two of R53 and R54 is connected to form a ring, wherein b3 is an integer of 0 to 4, and b4 is an integer of 0 to 5,
wherein each of R55 and R56 is hydrogen, or adjacent two of R55 and R56 is connected to form a ring,
wherein each of c1, c2 and c3 is independently 0 or a positive integer, and at least one of c1, c2 and c3 is the positive integer, and
wherein Dc1, Dc2 and Dc3 refer the number of hydrogens replaced with deuterium.

### Claim 2 (depends on 1)

The organic light emitting device according to claim 1, wherein the at least one organic material layer includes an emitting material layer, and the emitting material layer includes the first compound.

### Claim 3 (depends on 1)

The organic light emitting device according to claim 1, wherein the at least one organic material layer includes an electron auxiliary layer, and the electron auxiliary layer includes the first compound.

### Claim 4 (depends on 1)

The organic light emitting device according to claim 1, wherein the at least one organic material layer includes a hole blocking layer, and the hole blocking layer includes the first compound.

### Claim 5 (depends on 1)

The organic light emitting device according to claim 1, wherein a deuteration ratio of the second compound is 20% to 100%.

### Claim 6 (depends on 1)

The organic light emitting device according to claim 1, wherein c1 is the positive integer, and c2 and c3 are 0.

### Claim 7 (depends on 1)

The organic light emitting device according to claim 1, wherein the first emitting material layer further includes a third compound represented by Formula 12:
wherein each of R61, R62, R63 and R64 is independently selected from the group consisting of a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group and a substituted or unsubstituted C3 to C30 heteroaryl group, and
wherein each of e1, e2, e3 and e4 is independently an integer of 0 to 4, and n is an integer of 1 to 3.

### Claim 8 (depends on 7)

The organic light emitting device according to claim 7, wherein the third compound is one of compounds in Formula 13:

### Claim 9 (depends on 1)

The organic light emitting device according to claim 1, wherein the at least one organic material layer further includes a second emitting material layer between the first emitting material layer and the second electrode and a second electron blocking layer between the first and second emitting material layers.

### Claim 10 (depends on 1)

The organic light emitting device according to claim 1, wherein a deuteration ratio of the first compound is greater than that of the second compound.

### Claim 11 (depends on 1)

The organic light emitting device according to claim 1, wherein Formula 1 is represented by one of Formulas 3 to 6:
wherein the definitions of N-Het, R1 to R12, L, a, and b are same as those in Formula 1.

### Claim 12 (depends on 1)

The organic light emitting device according to claim 1, wherein Formula 1 is represented by one of Formula 7 or Formula 8:
wherein the definitions of N-Het, R1 to R12, L, a, and b are the same as those in Formula 1.

### Claim 13 (depends on 1)

The organic light emitting device according to claim 1, wherein Formula 1 is divided into structures in Formulas 1-1 to 1-3:
wherein the definitions of N-Het, R1 to R12, L, a, and b are same as those in Formula 1, and the mark
is a bonding position between the structures of Formulas 1-1 to 1-3,
wherein a deuteration ratio of the structure of Formula 1-1, the structure of Formula 1-2 or the structure of Formula 1-3 is 100%, or a deuteration ratio of the structure of Formula 1-1, the structure of Formula 1-2 and the structure of Formula 1-3 is 100%.

### Claim 14 (depends on 1)

The organic light emitting device according to claim 1, wherein N-Het in Formula 1 is represented by one of structures of Formula 1a:
wherein R21 to R25 are same or different,
wherein each of R21 to R25 is independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; 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 C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group, or adjacent two or more of R21 to R25 are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring,
wherein R is selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; 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 C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group.

### Claim 15 (depends on 1)

The organic light emitting device according to claim 1, wherein the first compound d is one of compounds in Formula 1c:

### Claim 16 (depends on 1)

The organic light emitting device according to claim 1, wherein the second compound is one of compounds of Formula 2b:

### Claim 17 (depends on 1)

The organic light emitting device according to claim 1, wherein the first electron blocking material is one of compounds in Formula 11: