# US 2018/0323397 A1 · Electron buffering materials, electron transport materials and organic electroluminescent device comprising the same

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2018/0323397 A1
- Document ID: US20180323397A1
- Status: Published application
- Kind: A1
- Application number: 15/770,215
- Filed: 2016-10-17
- Published: 2018-11-08
- Earliest claimed: 2015-10-30
- Assignees: Rohm and Haas Electronic Materials Korea Ltd.
- Applicants: Rohm and Haas Electronic Materials Korea Ltd.
- Inventors: Hee-Choon AHN; Sang-Hee CHO
- Web page: https://patentgrep.com/patent/US20180323397A1

## CPC

- C07D 277/60: condensed with carbocyclic rings or ring systems
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 403/10: linked by a carbon chain containing aromatic rings
- C07D 413/04: directly linked by a ring-member-to-ring-member bond
- C07D 413/10: linked by a carbon chain containing aromatic rings
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 413/14: containing three or more hetero rings
- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- C07D 417/10: linked by a carbon chain containing aromatic rings
- C07D 417/14: containing three or more hetero rings
- C07D 487/04: Ortho-condensed systems
- C07D 495/14: Ortho-condensed systems
- C07D 498/14: Ortho-condensed systems
- C07D 513/04: Ortho-condensed systems
- C09K 11/06: containing organic luminescent materials
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 85/324: {comprising aluminium, e.g. Alq3}
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- 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 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 50/165: comprising dopants
- H10K 50/166: {comprising a multilayered structure}
- H10K 50/17: Carrier injection layers
- H10K 50/171: {Electron injection layers}
- H10K 50/181: {Electron blocking layers}
- H10K 2101/40: Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
- 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 an electron buffering material, and an organic electroluminescent device comprising a first electrode, a second electrode facing the first electrode, a light-emitting layer between the first electrode and the second electrode, and an electron transport zone and an electron buffering layer between the light-emitting layer and the second electrode. The organic electroluminescent device comprising the electron buffering material of the present disclosure has low driving voltage, excellent luminous efficiency, and long lifespan.

## Claims

### Claim 1

An electron buffering material comprising a compound represented by the following formula 1:
wherein,
X1 represents —N═, —O— or —S—;
Y1 represents —N═, —NR8—, —O— or —S—; where X1 is —N═, Y1 is —NR8—, —O— or —S—; where X1 is —NR7—, Y1 is —N═, —O— or —S—; the case that both of X1 and Y1 are —O— or —S—, and the case that one of X1 and Y1 is —O—, and the other is —S— are excluded;
R1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3 to 30-membered)heteroaryl;
R2 to R4, R7 and R8, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3 to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;
a represents an integer of 1; b and c, each independently, represent an integer of 1 or 2; d represents an integer of 1 to 4; and
the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si and P.

### Claim 2 (depends on 1)

The electron buffering material according to claim 1, wherein formula 1 is represented by any one of the following formulae 2 to 4:
wherein
L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene,
X2 to X4, each independently, represent —N— or —CR9—,
Ar1 and Ar2, each independently, represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl,
R9 is as defined for R2 to R4,
Z represents a single bond, or a substituted or unsubstituted (C1-C6)alkylene,
W represents —NR10—, —O—, —S— or —CR11R12—,
R10 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl,
R11 and R12, each independently, represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl,
R5 and R6 are as defined for R2 to R4,
n represents 0 or 1, e and h, each independently, represent an integer of 1 to 3, f and g, each independently, represent an integer of 1 to 4, and
X1, Y1, R1 to R4, and a to c are as defined in claim 1.

### Claim 3 (depends on 1)

The electron buffering material according to claim 1, wherein the compound of formula 1 is selected from the group consisting of:

### Claim 4 (depends on 1)

An electron transport material comprising a compound represented by the following formula 1:
wherein, X1, Y1, R1 to R4, and a to d are as defined in claim 1.

### Claim 5 (depends on 2, 4)

The electron transport material according to claim 4, wherein formula 1 is represented by any of the following formulae 2 to 4:
wherein, X1 to X4, Y1, R1 to R6, L1, Ar1, Ar2, Z, a to c, e to g and n are as defined in claim 2.

### Claim 6 (depends on 4)

The electron transport material according to claim 4, wherein the compound of formula 1 is selected from the group consisting of:

### Claim 7 (depends on 4)

An organic electroluminescent device comprising a first electrode, a second electrode facing the first electrode, a light-emitting layer between the first electrode and the second electrode, and an electron transport zone between the light-emitting layer and the second electrode, wherein the electron transport zone comprises the electron transport material according to claim 4.

### Claim 8 (depends on 1)

An organic electroluminescent device comprising a first electrode, a second electrode facing the first electrode, a light-emitting layer between the first electrode and the second electrode, and an electron transport zone and an electron buffering layer between the light-emitting layer and the second electrode, wherein the electron buffering layer comprises the electron buffering material according to claim 1.

### Claim 9 (depends on 4, 8)

The organic electroluminescent device according to claim 8, wherein the electron transport zone comprises the electron transport material according to claim 4.

### Claim 10 (depends on 7)

The organic electroluminescent device according to claim 7, wherein the electron transport zone further comprises a reductive dopant.

### Claim 11 (depends on 9)

The organic electroluminescent device according to claim 9, wherein the electron transport zone further comprises a reductive dopant.