# US 12,004,420 B2 · Organic electroluminescent compound and organic electroluminescent device comprising the same

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- Number: US 12,004,420 B2
- Document ID: US12004420B2
- Status: Granted
- Kind: B2
- Application number: 16/886,822
- Filed: 2020-05-29
- Published: 2021-01-07
- Granted: 2024-06-04
- Earliest claimed: 2019-07-01
- Assignees: Rohm and Haas Electronic Materials Korea Ltd.
- Applicants: Rohm and Haas Electronic Materials Korea Ltd.
- Inventors: Doo-Hyeon Moon; Su-Hyun Lee; Jin-Ri Hong; So-Young Jung; Dong-Hyung Lee; Sang-Hee Cho
- Web page: https://patentgrep.com/patent/US12004420B2

## CPC

- 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 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- 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 50/16: Electron transporting layers
- H10K 50/18: Carrier blocking layers
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound, an organic electroluminescent device having a low driving voltage and/or a high luminous efficiency and/or a long lifespan can be provided.

## Claims

### Claim 1

A plurality of host materials comprising at least one first host material comprising an organic electroluminescent compound represented by the following formula 1-1 or 1-2 and at least one second host material, which is different from the first host material, wherein the second host material comprises the compound represented by the following formula 100:
wherein,
R1 and R2 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a ring;
R3, Ra and Rb each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)heteroaryl where the (C3-C30)heteroaryl group is selected from the group consisting of furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolizidinyl, acrylidinyl, silafluorenyl and germafluorenyl, 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;
L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene;
ETU is selected from any one of the substituents listed in the following Group 1;
Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (C3-C30)heteroaryl X represents CR11R12, O, or S;
R11 and R12 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted C3-C30)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a ring;
p represents an integer of 1 to 4, and when p is 2 or more, each R3 may be the same or different;
r represents an integer of 1 or 2, when r is 2, each Ra may be the same or different;
s represents an integer of 1 to 4, when s is 2 or more, each Rb may be the same or different; and
with the proviso that the compounds represented by the following formulas I-1 to I-3:
wherein,
R1, R2, and L1 are as defined in formula 1-1 and 1-2;
ETU1 to ETU3 are as defined as ETU in formula 1-1 and 1-2;
at least one of L1 and ETU1 include(s) triazine structure in formula I-1;
at least one of L1 and ETU2 include(s) pyridine structure, pyrimidine structure, or triazine structure in formula I-2; and
at least one of L1 and ETU3 include quinazoline structure in formula I-3, are excluded:
wherein,
V represents CX11X12, NX13, O or S;
L100 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (C3-C30)heteroarylene;
Ar100 represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)heteroaryl, or -NX9X10;
X9 and X10 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (C3-C30)heteroaryl;
X11 to X13, X101 and X102 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)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-(C2-C30) alkenylamino, a substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino, a substituted or unsubstituted mono- or di-(C3-C30)heteroarylamino, a substituted or unsubstituted (C1-C30)alkyl(C3-C30)heteroarylamino, a substituted or unsubstituted (C2-C30)alkenyl(C3-C30)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(C3-C30)heteroarylamino; and
j represents an integer of 1 to 4, k represents an integer of 1 to 6, and when j and k are 2 or more, each X101 and each X102 may be the same or different.

### Claim 2 (depends on 1)

The plurality of host materials according to claim 1, wherein Ar1 and Ar2 each independently are selected from any one of the substituents listed in the following Group 2.

### Claim 3 (depends on 1)

The plurality of host materials according to claim 1, wherein the compound represented by formula 1-1 or 1-2 is selected from the group consisting of:

### Claim 4 (depends on 1)

An organic electroluminescent device comprising the plurality of host materials according to claim 1.

### Claim 5 (depends on 4)

The organic electroluminescent device according to claim 4, wherein the organic electroluminescent compound is contained in a light-emitting layer and/or an electron transport zone.

### Claim 6 (depends on 1)

The host materials according to claim 1, wherein the compound represented by formula 100 is selected from the group consisting of: