# US 2025/0154136 A1 · Compound, and organic electroluminescent material and organic electroluminescent device comprising the same

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- Number: US 2025/0154136 A1
- Document ID: US20250154136A1
- Status: Published application
- Kind: A1
- Application number: 18/928,865
- Filed: 2024-10-28
- Published: 2025-05-15
- Earliest claimed: 2023-11-02
- Applicants: DuPont Specialty Materials Korea Ltd.
- Inventors: Doo-Hyeon MOON; Mi-Ja LEE; Tae-Jun HAN; Kyoung-Jin PARK; Eun-Young LEE
- Web page: https://patentgrep.com/patent/US20250154136A1

## CPC

- C07D 405/14: containing three or more hetero rings
- C07B 59/004: {Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur, selenium or tellurium}
- C07D 409/14: containing three or more hetero rings
- C07D 487/04: Ortho-condensed systems
- H10K 85/342: {comprising iridium}
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/656: {comprising two or more different heteroatoms per ring (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}
- C07B 2200/05: Isotopically modified compounds, e.g. labelled
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

The present disclosure relates to a compound, and an organic electroluminescent material and an organic electroluminescent device comprising the same. By comprising the compound and/or the organic electroluminescent material according to the present disclosure, an organic electroluminescent device can be provided which has low driving voltage and/or high luminous efficiency and/or long lifespan characteristics compared to conventional organic electroluminescent devices.

## Claims

### Claim 1

A compound represented by the following Formula 1:
wherein,
X1 to X3 each independently represent CR5 or N, provided that at least one of X1 to X3 is N;
Ar1 represents hydrogen, deuterium, halogen, cyano, amino, 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, —Si(R11)(R12)(R13), or —N(R14)(R15);
R11 to R15 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
Ar represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
R1 to R5 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 (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, or a substituted or unsubstituted tri(C6-C30)arylsilyl; or may be linked to the adjacent substituents to form a ring(s); and
a, b, and d each independently represent an integer of 1 to 4, c represents an integer of 1 to 3, and when a to d are an integer of 2 or more, each of R1 to R4 may be the same as or different from each other.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein the substituted alkyl, the substituted alkenyl, the substituted cycloalkyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, and the substituted triarylsilyl, each independently are substituted with at least one selected from the group consisting of deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (C6-C30)aryl unsubstituted or substituted with at least one of (C1-C30)alkyl and di(C6-C30)arylamino; (3- to 30-membered)heteroaryl unsubstituted or substituted with at least one (C6-C30)aryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; a fused ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring; amino; mono- or di(C1-C30)alkylamino; mono- or di(C2-C30)alkenylamino; mono- or di(C6-C30)arylamino unsubstituted or substituted with (C1-C30)alkyl; mono- or di(3- to 30-membered)heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl(3- to 30-membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(3- to 30-membered)heteroarylamino; (C6-C30)aryl(3- to 30-membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein Formula 1 is represented by the following Formula 1-1:
wherein,
R1 to R4, X1 to X3, Ar1, L1, and a to d are as defined in claim 1;
X represents O, S, or Se;
R6 and R7 are as defined as R1 in claim 1; and
e represents an integer of 1 to 3, f represents an integer of 1 to 4, and when e and f are an integer of 2 or more, each of R6 and each of R7 may be the same as or different from each other.

### Claim 4 (depends on 1)

The compound according to claim 1, wherein the compound represented by Formula 1 is selected from the following compounds:
wherein “Dn” in the above compounds means that n number of hydrogens is replaced by deuterium, wherein n represents an integer of 1 or more, and the upper limit of n is determined by the number of hydrogens that can be substituted in each compound.

### Claim 5 (depends on 1)

An organic electroluminescent material, comprising the compound represented by Formula 1 according to claim 1 and a compound represented by the following Formula 2 or 3:
wherein,
A1 and A2 each independently represent a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted carbazolyl;
any one of X15 to X18 and any one of X19 to X22 are linked to each other to form a single bond; and
X11 to X14, X23 to X26, and X15 to X22 which do not form a single bond each independently represent hydrogen, deuterium, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or may be linked to the adjacent substituents to form a ring(s);
wherein,
A3 represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted dibenzoselenophenyl, or a substituted or unsubstituted carbazolyl;
L2 represents a single bond or a substituted or unsubstituted (C6-C30)arylene;
a pair of adjacent X35 to X38 are linked to the following Formula 3-A to form a ring, and X35 to X38 which do not form a ring and X31 to X34 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; and
wherein,
A4 represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted dibenzoselenophenyl, or a substituted or unsubstituted carbazolyl;
L3 represents a single bond or a substituted or unsubstituted (C6-C30)arylene; and
X41 to X44 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl.

### Claim 6 (depends on 5)

The organic electroluminescent material according to claim 5, wherein at least one of X11, X18, X19, and X26 in Formula 2 is deuterium.

### Claim 7 (depends on 5)

The organic electroluminescent material according to claim 5, wherein the deuterium substitution rate of X11 to X26 in Formula 2 is 25% to 100%.

### Claim 8 (depends on 5)

The organic electroluminescent material according to claim 5, wherein the deuterium substitution rate of the compound represented by Formula 2 or 3 is 40% to 100%.

### Claim 9 (depends on 5)

The organic electroluminescent material according to claim 5, wherein Formula 2 is represented by any one of the following Formulas 2-1 to 2-8.
wherein,
A1, A2, and X11 to X26 each independently are as defined in claim 5.

### Claim 10 (depends on 5)

The organic electroluminescent material according to claim 5, wherein A1 and A2 in Formula 2 each independently represent phenyl unsubstituted or substituted with deuterium; biphenyl unsubstituted or substituted with deuterium; terphenyl unsubstituted or substituted with deuterium; naphthyl unsubstituted or substituted with deuterium; fluorenyl unsubstituted or substituted with at least one of deuterium, (C1-C30)alkyl, and (C6-C30)aryl; benzofluorenyl unsubstituted or substituted with at least one of deuterium, (C1-C30)alkyl, and (C6-C30)aryl; triphenylenyl unsubstituted or substituted with deuterium; fluoranthenyl unsubstituted or substituted with deuterium; phenanthrenyl unsubstituted or substituted with deuterium; dibenzofuranyl unsubstituted or substituted with deuterium; dibenzothiophenyl unsubstituted or substituted with deuterium; carbazolyl unsubstituted or substituted with deuterium; or a combination thereof.

### Claim 11 (depends on 5)

The organic electroluminescent material according to claim 5, wherein Formula 3 is represented by any one of the following Formulas 3-1 to 3-6.
wherein,
A3, A4, L2, L3, X31 to X38, and X41 to X44 are as defined in claim 5.

### Claim 12 (depends on 5)

The organic electroluminescent material according to claim 5, wherein the compound represented by Formula 2 is selected from the following compounds:
wherein “Dn” in the above compounds means that n number of hydrogens is replaced by deuterium.

### Claim 13 (depends on 5)

The organic electroluminescent material according to claim 5, wherein the compound represented by Formula 3 is selected from the following compounds:
wherein “Dn” in the above compounds means that n number of hydrogens is replaced by deuterium, wherein n represents an integer of 1 or more, and the upper limit of n is determined by the number of hydrogens that can be substituted in each compound.

### Claim 14 (depends on 1)

An organic electroluminescent device, comprising a first electrode; a second electrode; and at least one light-emitting layer interposed between the first electrode and the second electrode, wherein the at least one light-emitting layer comprises a compound according to claim 1.

### Claim 15 (depends on 5)

An organic electroluminescent device, comprising a first electrode; a second electrode; and at least one light-emitting layer interposed between the first electrode and the second electrode, wherein the at least one light-emitting layer comprises an organic electroluminescent material according to claim 5.