# US 12,120,948 B2 · Boron-containing compound and organic light-emitting element comprising same

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- Number: US 12,120,948 B2
- Document ID: US12120948B2
- Status: Granted
- Kind: B2
- Application number: 17/284,760
- Filed: 2020-02-13
- Published: 2021-12-16
- Granted: 2024-10-15
- Earliest claimed: 2019-02-13
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Sujeong Geum; Kyunghee Kim; Wanpyo Hong; Jaegoo Lee; Sang Duk Suh
- Web page: https://patentgrep.com/patent/US12120948B2

## CPC

- C07F 7/0812: {comprising a heterocyclic ring}
- C09K 11/06: containing organic luminescent materials
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/658: {Organoboranes}
- C07B 2200/05: Isotopically modified compounds, e.g. labelled
- C09K 2211/1018: Heterocyclic compounds
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 50/17: Carrier injection layers
- H10K 50/171: {Electron injection layers}
- H10K 2101/10: Triplet emission
- 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
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

A compound represented by Chemical Formula 1, and an organic light emitting device comprising the same, the compound used in an organic material layer of the organic light emitting device, and providing low driving voltage and high efficiency properties of the organic light emitting device.

## Claims

### Claim 1

A compound of Chemical Formula 1:
wherein, in Chemical Formula 1:
A1, A2, A3, B1 and B2 are the same as or different from each other, and are each independently a hydrocarbon ring;
Ar1, Ar2, Ar4 and Ar5 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group;
Ar3 and Ar6 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;
R1 and R3 are the same as or different from each other, and are each independently deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group;
R2 and R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group;
R4 is deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted heterocyclic group;
n1 to n3 and n5 are each an integer of 0 to 10, n4 is an integer of 1 to 10, and when any of n1 to n5 is 2 or greater, the two or more substituents in the parentheses are the same as or different from each other;
n1+n3 is 1 or greater; and
m1 and m2 are each 0 or 1, and m1+m2 is 1.

### Claim 2 (depends on 1)

The compound of claim 1, wherein A1, A2, A3, B1 and B2 are the same as or different from each other, and are each independently an aromatic hydrocarbon ring having 6 to 30 carbon atoms.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R4 is deuterium, a halogen group, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms and comprising one or more heteroatoms selected from the group consisting of O, S, N and Si.

### Claim 4 (depends on 1)

The compound of claim 1, wherein the compound of Chemical Formula 1 is represented by the following Chemical Formula 2 or 3:
wherein, in Chemical Formulae 2 and 3,
A1, A2, A3, B1, B2, R1 to R5, n1 to n5 and Ar1 to Ar6 are the same as defined in Chemical Formula 1.

### Claim 5 (depends on 1)

The compound of claim 1, wherein the compound of Chemical Formula 1 is represented by—the following Chemical Formula 4:
wherein, in Chemical Formula 4,
A1, A3, B1, R1 to R5, n1 to n3, Ar1 to Ar6, m1 and m2 are the same as defined in Chemical Formula 1, and
n11 is an integer of 1 to 5, n12 is an integer of 0 to 4, and when n11 and n12 are 2 or greater, the two or more substituents in the parentheses are the same as or different from each other.

### Claim 6 (depends on 1)

The compound of claim 1, wherein the compound of Chemical Formula 1 is represented by the following Chemical Formula 5:
wherein, in Chemical Formula 5,
R1 to R5, Ar1 to Ar6, m1 and m2 are the same as defined in Chemical Formula 1, and
n11 is an integer of 1 to 5, n14 is an integer of 0 to 5, n12 and n13 are each an integer of 0 to 4, and n15 is an integer of 0 to 3, and when any of n11 to n15 are 2 or greater, the two or more substituents in the parentheses are the same as or different from each other, and n13+n15 is 1 or greater.

### Claim 7 (depends on 1)

The compound of claim 1, wherein the compound of Chemical Formula 1 is represented by the following Chemical Formula 6 or 7:
wherein, in Chemical Formulae 6 and 7,
R1 to R5 and Ar1 to Ar6 are the same as defined in Chemical Formula 1, and
n11 is an integer of 1 to 5, n14 is an integer of 0 to 5, n12 and n13 are each an integer of 0 to 4, n15 and n12′ are each an integer of 0 to 3, n11′ is an integer of 1 to 4, and when any of n11 to n15, n11′ or n12′ are 2 or greater, the two or more substituents in the parentheses are the same as or different from each other, and n13+n15 is 1 or greater.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the compound of Chemical Formula 1 is any one compound selected from among the following compounds:

### Claim 9 (depends on 1)

The compound of claim 1, which is a fluorescence dopant for a thermally activated delayed fluorescence device.

### Claim 10 (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 compound of claim 1.

### Claim 11 (depends on 10)

The organic light emitting device of claim 10, wherein the organic material layer comprises a hole injection layer or a hole transfer layer, and the hole injection layer or the hole transfer layer comprises the compound.

### Claim 12 (depends on 10)

The organic light emitting device of claim 10, wherein the organic material layer comprises an electron transfer layer or an electron injection layer, and the electron transfer layer or the electron injection layer comprises the compound.

### Claim 13 (depends on 10)

The organic light emitting device of claim 10, wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the compound.

### Claim 14 (depends on 13)

The organic light emitting device of claim 13, wherein the light emitting layer comprises the compound as a dopant.

### Claim 15 (depends on 13)

The organic light emitting device of claim 13, wherein the light emitting layer comprises the compound as a thermally activated delayed fluorescence dopant.

### Claim 16 (depends on 10)

The organic light emitting device of claim 10, wherein the organic material layer comprises one or more of a hole transfer layer, a hole injection layer, an electron blocking layer, a layer carrying out hole transfer and hole injection at the same time, a light emitting layer, an electron transfer layer, an electron injection layer, a hole blocking layer, and a layer carrying out electron transfer and electron injection at the same time.