# US 2025/0098537 A1 · Electronic barrier material and organic semiconductor element

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- Number: US 2025/0098537 A1
- Document ID: US20250098537A1
- Status: Published application
- Kind: A1
- Application number: 18/722,157
- Filed: 2022-11-29
- Published: 2025-03-20
- Earliest claimed: 2021-12-23
- Assignees: Kyulux, Inc.
- Applicants: Kyulux, Inc.
- Inventors: Hiroaki OZAWA; Takahiro KASHIWAZAKI; Aiko GOTO; Tomoki YUKAWA; Momoko MORIO; Songhye HWANG; Makoto YOSHIZAKI; Ayataka ENDO
- Web page: https://patentgrep.com/patent/US20250098537A1

## CPC

- H10K 85/658: {Organoboranes}
- C07D 491/048: the oxygen-containing ring being five-membered
- C09K 11/06: containing organic luminescent materials
- H10K 50/00: Organic light-emitting devices (integrated devices or assemblies of multiple devices H10K59/00, H10K65/00; organic semiconductor lasers H01S5/36)
- H10K 50/10: OLEDs or polymer light-emitting diodes [PLED]
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/18: Carrier blocking layers
- H10K 50/81: Anodes
- H10K 50/82: Cathodes
- H10K 85/322: {comprising boron}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- 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 2101/20: Delayed fluorescence emission
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

A compound represented by the following general formula is useful as an electron barrier material. R1 to R21 each are H, a deuterium atom, or a substituent except a cyano group; X represents O or S.

## Claims

### Claim 1

An electron barrier material containing a compound represented by the following general formula (1):
wherein R1 to R21 each independently represent a hydrogen atom, a deuterium atom, or a substituent not including a cyano group;
one combination of R2 and R13, R13 and R14, and R14 and R15 can bond to each other to form a benzofuro skeleton or a benzothieno skeleton;
R1 to R11, and R16 to R21 do not bond to the other R1 to R11, R16 to R21 or R12 to R15 to form a cyclic structure; and
X represents an oxygen atom or a sulfur atom.

### Claim 2 (depends on 1)

The electron barrier material according to claim 1, wherein R1 to R21 do not bond to the other R1 to R21 to form a cyclic structure.

### Claim 3 (depends on 1)

The electron barrier material according to claim 1, wherein R1 to R21 each independently represent a hydrogen atom, a deuterium atom, an optionally-deuterated alkyl group, or an optionally-deuterated phenyl group.

### Claim 4 (depends on 1)

The electron barrier material according to claim 1, wherein R1 to R11, R20 and R21 each independently represent a hydrogen atom or a deuterium atom.

### Claim 5 (depends on 1)

The electron barrier material according to claim 1, wherein R12 to R15 each independently represent a hydrogen atom or a deuterium atom.

### Claim 6 (depends on 1)

The electron barrier material according to claim 1, wherein R16 to R19 each independently represent a hydrogen atom or a deuterium atom.

### Claim 7 (depends on 1)

The electron barrier material according to claim 1, wherein X is an oxygen atom.

### Claim 8 (depends on 1)

The electron barrier material according to claim 1, which is used in combination with a compound represented by the following general formula (G):
wherein one of X1 and X2 is a nitrogen atom, and the other is a boron atom;
R1 to R26, A1 and A2 each independently represent a hydrogen atom, a deuterium atom, or a substituent;
R1 and R2, R2 and R3, R3 and R4, R4 and R5, R5 and R6, R6 and R7, R7 and R8, R8 and R9, R9 and R10, R10 and R11, R11 and R12, R13 and R14, R14 and R15, R15 and R16, R16 and R17, R17 and R18, R18 and R19, R19 and R20, R20 and R21, R21 and R22, R22 and R23, R23 and R24, R24 and R25, and R25 and R26 can bond to each other to form a cyclic structure; and
provided that when X1 is a nitrogen atom, R17 and R18 bond to each other to be a single bond to form a pyrrole ring, and when X2 is a nitrogen atom, R21 and R22 bond to each other to be a single bond to form a pyrrole ring.

### Claim 9 (depends on 1)

An organic semiconductor device containing the electron barrier material according to claim 1.

### Claim 10 (depends on 9)

The organic semiconductor device according to claim 9, wherein the organic semiconductor device is an organic electroluminescent device having an anode, a cathode, and at least two organic layers containing an electron barrier layer that contains the above electron barrier material and a light emitting layer, between the anode and the cathode.

### Claim 11 (depends on 10)

The organic semiconductor device according to claim 10, wherein the light emitting layer contains a host material and a delayed fluorescent material.

### Claim 12 (depends on 10)

The organic semiconductor device according to claim 10, wherein the light emitting layer contains a host material, a delayed florescent material and a fluorescence emitting material, and the amount of light emitted from the fluorescence emitting material is the largest among the light from the device.

### Claim 13 (depends on 10)

The organic semiconductor device according to claim 10, wherein the light emitting layer is adjacent to the electron barrier layer.

### Claim 14 (depends on 10)

The organic semiconductor device according to claim 10, wherein the light emitting layer contains the compound represented by the following general formula (G):
wherein one of X1 and X2 is a nitrogen atom, and the other is a boron atom;
R1 to R26, A1 and A2 each independently represent a hydrogen atom, a deuterium atom, or a substituent;
R1 and R2, R2 and R3, R3 and R4, R4 and R5, R5 and R6, R6 and R7, R7 and R8, R8 and R9, R9 and R10, R10 and R11, R11 and R12, R13 and R14, R14 and R15, R15 and R16, R16 and R17, R17 and R18, R18 and R19, R19 and R20, R20 and R21, R21 and R22, R22 and R23, R23 and R24, R24 and R25, and R25 and R26 can bond to each other to form a cyclic structure;
provided that when X1 is a nitrogen atom, R17 and R18 bond to each other to be a single bond to form a pyrrole ring, and when X2 is a nitrogen atom, R21 and R22 bond to each other to be a single bond to form a pyrrole ring.