# US 12,600,903 B2 · Delayed fluorescence compound, and organic light-emitting device comprising same

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- Number: US 12,600,903 B2
- Document ID: US12600903B2
- Status: Granted
- Kind: B2
- Application number: 18/039,108
- Filed: 2021-04-20
- Published: 2024-05-02
- Granted: 2026-04-14
- Earliest claimed: 2020-11-26
- Assignees: University-Industry Cooperation Group of Kyung Hee University
- Applicants: University-Industry Cooperation Group of Kyung Hee University
- Inventors: Jang Hyuk Kwon; Ju Young Lee; Ramanaskanda Braveenth; Kijoon Yang; Hyuna Lee
- Web page: https://patentgrep.com/patent/US12600903B2

## CPC

- C09K 11/06: containing organic luminescent materials
- C07F 5/027: {Organoboranes and organoborohydrides}
- H10K 85/658: {Organoboranes}
- C09K 2211/1018: Heterocyclic compounds
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/12: comprising dopants
- H10K 2101/20: Delayed fluorescence emission
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

The present specification relates to a delayed fluorescence compound represented by chemical formula 1 and an organic light-emitting device comprising same, and achieves delayed fluorescence light sensitive hyperfluorescence properties by the use of a compound that exhibits deep blue properties and has a low singlet-triplet energy difference, and a fluorescence compound which, relative to conventional delayed fluorescence material, exhibits deep blue properties, has a narrow half-width, and has excellent color purity.

## Claims

### Claim 1

A delayed fluorescence compound represented by Chemical Formula 1 below:
in Chemical Formula 1, D3 is represented by Chemical Formula 2 below,
in the above Chemical Formulae, A1 to A6 are each independently a ring structure selected from a substituted or unsubstituted C5-C60 carbocyclic group, a substituted or unsubstituted C2-C60 heterocyclic group, a C6-C60 aryl group, and a C5-C60 heteroaryl group, X1 and X2 are each independently O, N—R7, C(R8)2, or S; at least one of X1 and X2 is not N—R7; Y1 and Y2 are each independently selected from O or S; L3 is a single bond or C6-C60 arylene; R1 to R6 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group; and R7 and R8 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C6-C60 heteroaryl group.

### Claim 2 (depends on 1)

The delayed fluorescence compound of claim 1, wherein the delayed fluorescence compound is any one of compounds represented by the following Chemical Formulas T-1 to T-144:

### Claim 3 (depends on 1)

An organic light-emitting device comprising:
a first electrode;
a second electrode provided to face the first electrode; and
one or more organic material layers interposed between the first electrode and the second electrode,
wherein one or more of the organic material layers include one or more of the delayed fluorescence compounds according to claim 1.

### Claim 4 (depends on 3)

The organic light-emitting device of claim 3, wherein one or more of the organic material layers include a fluorescence compound represented by Chemical Formula 3 below:
in Chemical Formula 3, R9 to R13 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group; and X3 to X6 are each independently hydrogen or bind together to form a ring.

### Claim 5 (depends on 4)

The organic light-emitting device of claim 4, wherein the fluorescence compound represented by Chemical Formula 3 is represented by any one of the following Chemical Formulas F-1 to F-35:

### Claim 6 (depends on 3)

The organic light-emitting device of claim 3, wherein the first electrode is an anode, the second electrode is a cathode, and the organic material layer comprises: a light-emitting layer comprising the one or more of the delayed fluorescence compounds; a hole transport region interposed between the first electrode and the light-emitting layer and including at least one of a hole injection layer, a hole transport layer, and an electron blocking layer; and an electron transport region interposed between the light-emitting layer and the second electrode and including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.

### Claim 7 (depends on 4)

The organic light-emitting device of claim 4, wherein the first electrode is an anode, the second electrode is a cathode, and the organic material layer comprises: a light-emitting layer including the one or more of the delayed fluorescence compounds and the fluorescence compound represented by Chemical Formula 3; a hole transport region interposed between the first electrode and the light-emitting layer and including at least one of a hole injection layer, a hole transport layer, and an electron blocking layer; and an electron transport region interposed between the light-emitting layer and the second electrode and including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.