# US 2021/0175475 A1 · Organic light-emitting element

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- Number: US 2021/0175475 A1
- Document ID: US20210175475A1
- Status: Published application
- Kind: A1
- Application number: 16/761,553
- Filed: 2018-11-15
- Published: 2021-06-10
- Earliest claimed: 2017-11-23
- Assignees: Toray Industries, Inc.
- Applicants: Toray Industries, Inc.
- Inventors: Peng Wang; Guangnan Jin; Takeshi Ikeda; Jincai Li; Daisaku Tanaka
- Web page: https://patentgrep.com/patent/US20210175475A1

## CPC

- H10K 85/658: {Organoboranes}
- C07F 5/04: Esters of boric acids
- H10K 59/879: {comprising refractive means, e.g. lenses}
- H10K 85/322: {comprising boron}
- H10K 2102/3026: {Top emission}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

The present invention provides an organic light-emitting element, comprising a substrate, a first electrode, more than one organic layer film comprising a light-emitting layer, and a second electrode. The light-emitting element further comprises a cover layer. The cover layer is located on the second electrode, and comprises a high refractive layer and a low refractive layer. A material for the low refractive layer of the cover layer is a boron complex organic small molecular compound. The organic light-emitting element provided by the present invention can achieve high light-emitting efficiency and color reproducibility. The organic light-emitting element of the present invention can be used for an organic EL display, a backlight source of a liquid crystal display, illumination, a sign board, an identification lamp, etc.

## Claims

### Claim 1

An organic light-emitting element, comprising a substrate, a first electrode, more than one organic layer film comprising a light-emitting layer, and a second electrode, wherein the light-emitting element further comprises a cover layer; the cover layer comprises a low refractive layer; and the low refractive layer is formed from an organic small molecular compound.

### Claim 2 (depends on 1)

The organic light-emitting element according to claim 1, wherein the cover layer is disposed on the second electrode, and the cover layer comprises a high refractive layer and the low refractive layer.

### Claim 3 (depends on 2)

The organic light-emitting element according to claim 2, wherein the high refractive layer has a refractive index of 1.8 or more; and the low refractive layer has a refractive index of 1.5 to 1.7.

### Claim 4 (depends on 2)

The organic light-emitting element according to claim 2, wherein a difference between the refractive index of the high refractive layer and the refractive index of the low refractive layer is 0.3 or more.

### Claim 5 (depends on 1)

The organic light-emitting element according to claim 1, wherein the high refractive layer is formed from at least one of the following inorganic compounds and organic compounds, wherein the inorganic compound is one or more of SiOx, SiNy, ZnS, ZnSe, ZrO or TiO2, in which said x, y are independently an integer from 1 to 4; the organic compound is one or more an arylamine derivative, a carbazole derivative, a benzimidazole derivative or a triazole derivative.

### Claim 6 (depends on 1)

The organic light-emitting element according to claim 1, which contains a boron complex compound.

### Claim 7 (depends on 1)

The organic light-emitting element according to claim 1, wherein the low refractive layer of the cover layer contains a boron complex compound.

### Claim 8 (depends on 6)

The organic light-emitting element according to claim 6, wherein the boron complex compound is represented by the following formula 1:
in which, R1 to R4 are the same or different and are each independently selected from one or more of the group consisting of hydrogen, deuterium, optionally substituted alkyl group, optionally substituted cycloalkyl group, optionally substituted heterocyclic group, optionally substituted alkenyl group, optionally substituted cycloalkenyl group, optionally substituted alkynyl group, optionally substituted alkoxyl group, optionally substituted alkyl sulphanyl group, optionally substituted aryl ether group group, optionally substituted aryl sulfide group group, optionally substituted aryl group, optionally substituted heteroaryl group, optionally substituted carbonyl group, optionally substituted carboxyl group, optionally substituted oxycarbonyl group, optionally substituted carbamoyl group, optionally substituted alkylamino group, or optionally substituted silanyl group; R5 to R6 are the same or different and are each independently selected from fluorine, alkoxyl group, aryl ether group or aryl group; R1 and R2 can be bonded to form a ring; and
in the case of being substituted, substituents are each independently selected from one or more of the group consisting of deuterium, halogen, C1-C15 alkyl group, C3-C15 cycloalkyl group, C3-C15 heterocyclic group, C2-C15 alkenyl group, C4-C15 cycloalkenyl group, C2-C15 alkynyl group, C1-C15 alkoxyl group, C1-C15 alkyl sulphanyl group, C6-C55 aryl ether group, C6-C55 aryl sulfide group, C6-C55 aryl group, C5-C55 aromatic heterocyclic group, carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, C1-C40 alkylamino group or C3-C15 silanyl group with 1-5 silicon atoms.

### Claim 9 (depends on 8)

The organic light-emitting element according to claim 8, wherein R5 to R6 are fluorine.

### Claim 10 (depends on 8)

The organic light-emitting element according to claim 8, wherein the boron complex compound is represented by the following formula 2:
in which, R7 to R14 are the same or different and are each independently selected from one or more of the group consisting of hydrogen, deuterium, optionally substituted alkyl group, optionally substituted cycloalkyl group, optionally substituted heterocyclic group, optionally substituted alkenyl group, optionally substituted cycloalkenyl group, optionally substituted alkynyl group, optionally substituted alkoxyl group, optionally substituted alkyl sulphanyl group, optionally substituted aryl ether group group, optionally substituted aryl sulfide group group, optionally substituted aryl group, optionally substituted heteroaryl group, optionally substituted carbonyl group, optionally substituted carboxyl group, optionally substituted oxycarbonyl group, optionally substituted carbamoyl group, optionally substituted alkylamino group, or optionally substituted silanyl group; R13 to R14 may be bonded to form a ring; R15 to R18 are the same or different and are each independently selected from fluorine, alkoxyl group, aryl ether group or aryl group; n is an integer from 1 to 3; R7 and R8 can be bonded to form a ring; and R10 and R11 can be bonded to form a ring; and
in the case of being substituted, substituents are each independently selected from one or more of the group consisting of deuterium, halogen, C1-C15 alkyl group, C3-C15 cycloalkyl group, C3-C15 heterocyclic group, C2-C15 alkenyl group, C4-C15 cycloalkenyl group, C2-C15 alkynyl group, C1-C15 alkoxyl group, C1-C15 alkyl sulphanyl group, C6-C55 aryl ether group, C6-C55 aryl sulfide group, C6-C55 aryl group, C5-C55 aromatic heterocyclic group, carbonyl group, carboxyl group, oxycarbonyl group, carbamoyl group, C1-C40 alkylamino group or C3-C15 silanyl group with 1-5 silicon atoms.

### Claim 11 (depends on 10)

The organic light-emitting element according to claim 10, wherein R15 to R18 are fluorine.

### Claim 12 (depends on 10)

The organic light-emitting element according to claim 10, wherein the boron complex compound is represented by the following formula 3:
in which, R19 to R30 are the same or different and are each independently selected from one or more of the group consisting of hydrogen, deuterium, optionally substituted alkyl group, optionally substituted cycloalkyl group, optionally substituted heterocyclic group, optionally substituted alkenyl group, optionally substituted cycloalkenyl group, optionally substituted alkynyl group, optionally substituted alkoxyl group, optionally substituted alkyl sulphanyl group, optionally substituted aryl ether group group, optionally substituted aryl sulfide group group, optionally substituted aryl group, optionally substituted heteroaryl group, optionally substituted carbonyl group, optionally substituted carboxyl group, optionally substituted oxycarbonyl group, optionally substituted carbamoyl group, optionally substituted alkylamino group, or optionally substituted silanyl group; R29 to R30 may also be bonded to form a ring; R31 to R34 are the same or different and are each independently selected from fluorine, alkoxyl group, aryl ether group or aryl group; n is an integer from 1 to 3; and
in the case of being substituted, substituents are each independently selected from one or more of the group consisting of deuterium, halogen, C1-C6 alkyl group, C3-C6 cycloalkyl group, C3-C6 heterocyclic group, C2-C6 alkenyl group, C4-C6 cycloalkenyl group, C2-C6 alkynyl group, C1-C6 alkoxyl group, or C1-C6 alkyl sulphanyl group.

### Claim 13 (depends on 12)

The organic light-emitting element according to claim 12, wherein at least three of R19 to R22 and R24 to R27 are not hydrogen.

### Claim 14 (depends on 12)

The organic light-emitting element according to claim 12, wherein R31 to R34 are fluorine.

### Claim 15 (depends on 10)

The organic light-emitting element according to claim 10, wherein n is 1.
