IP Library Granted Patent US 12686661
Granted Patent B2
US 12686661 · App. 17/632,875 · Granted Jul 21, 2026

Compound and organic light emitting device comprising the same

Inventors: Sang Duk Suh (Daejeon, KR); Min Woo Jung (Daejeon, KR); Jungha Lee (Daejeon, KR); Su Jin Han (Daejeon, KR); Seulchan Park (Daejeon, KR); Sunghyun Hwang (Daejeon, KR); Dong Hoon Lee (Daejeon, KR)
Assignee: LG CHEM, LTD.
C07D209/86C07D403/04C07D405/14C07D409/14C07D487/04C07D491/048C07D495/04H10K50/11H10K50/157H10K50/16H10K85/6572H10K85/6574H10K85/6576C07B2200/05
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Quick Facts
Patent No.
US 12686661
App. No.
17/632,875
Granted
Jul 21, 2026
Kind
B2
Abstract

Provided is a compound of Chemical Formula 1: wherein: each X is independently N or CH, provided that at least one X is N; Y is O or S; each Ar is independently substituted or unsubstituted: C 6-60 aryl or C 5-60 heteroaryl containing N, O or S; each R 1 , R 2 , R 3 , and R 4 independently is hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted: C 1-60 alkyl, C 1-60 alkoxy, C 2-60 alkenyl, C 2-60 alkynyl, C 3-60 cycloalkyl, C 6-60 aryl, or C 2-60 heteroaryl containing N, O or S, or two adjacent R 4S combine to form a C 4-60 aliphatic or aromatic ring; n1, n2, and n3 are each independently 0 or 1, and n4 is 1 to 4, provided that at least one of Ar is substituted with deuterium, or at least one of R 1 , R 2 , R 3 , or R 4 is, or is substituted with, one or more deuterium, and an organic light-emitting diode comprising same.

Claims (69)

1 . An organic light emitting device, comprising:

a first electrode;

a second electrode that is provided opposite to the first electrode; and

one or more organic material layers that are provided between the first electrode and the second electrode, wherein at least one layer of the organic material layers comprises a compound of Chemical Formula 1, and the organic material layer comprising the compound is a light emitting layer:

wherein in the Chemical Formula 1:

each X is independently N or CH, provided that at least one of X is N;

Y is O or S;

each Ar is independently substituted or unsubstituted C 6-60 aryl; or substituted or unsubstituted C 5-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S;

R 1 , R 2 , and R 3 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 1-60 alkyl, substituted or unsubstituted C 1-60 alkoxy, substituted or unsubstituted C 2-60 alkenyl, substituted or unsubstituted C 2-60 alkynyl, substituted or unsubstituted C 3-60 cycloalkyl, substituted or unsubstituted C 6-60 aryl, or substituted or unsubstituted C 2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S;

each R 4 is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 1-60 alkyl, substituted or unsubstituted C 1-60 alkoxy, substituted or unsubstituted C 2-60 alkenyl, substituted or unsubstituted C 2-60 alkynyl, substituted or unsubstituted C 3-60 cycloalkyl, substituted or unsubstituted C 6-60 aryl, or substituted or unsubstituted C 2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S, or two adjacent Ras combine with each other to form a C 4-60 aliphatic or aromatic ring;

n1, n2, and n3 are each independently 0 or 1; and

n4 is an integer of 1 to 4,

provided that at least one of Ar is substituted with one or more deuterium, at least one of R 1 , R 2 , R 3 , or R 4 is substituted with one or more deuterium, or at least one of R 1 , R 2 , R 3 , and R 4 is deuterium;

wherein the light emitting layer further comprises a compound of the following Chemical Formula 2:

wherein in the Chemical Formula 2:

Ar 1 and Ar 2 are independently substituted or unsubstituted C 6-60 aryl or substituted or unsubstituted C 5-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S;

R 7 and R 8 are each independently hydrogen, deuterium, halogen, cyano, nitro, amino, substituted or unsubstituted C 1-60 alkyl, substituted or unsubstituted C 3-60 cycloalkyl, substituted or unsubstituted C 2-60 alkenyl, substituted or unsubstituted C 6-60 aryl, or substituted or unsubstituted C 5-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S; and

p and q are each independently an integer of 0 to 7.

2 . The organic light emitting device of claim 1 , wherein Ar 1 and Ar 2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl.

3 . The organic light emitting device of claim 1 , wherein the compound of Chemical Formula 2 is any one compound selected from the group consisting of the following compounds:

4 . An organic light emitting device comprising:

a first electrode;

a second electrode that is provided opposite to the first electrode; and

one or more organic material layers that are provided between the first electrode and the second electrode, wherein at least one layer of the one or more organic material layers is a light emitting layer comprising a compound of Chemical Formula 1:

wherein in the Chemical Formula 1:

each X is independently N or CH, provided that at least one of X is N;

Y is O or S;

at least one of Ar is phenyl, biphenylyl, or phenyl substituted with five deuteriums, and the rest of Ar are any one of phenyl, biphenylyl, dibenzofuranyl, or dibenzothiophenyl;

R 1 , R 2 , and R 3 are each independently hydrogen or deuterium;

each R 4 is independently hydrogen or deuterium, or two adjacent Ras combine with each other to form a 1,1′-dimethyl-indene, benzofuran, benzothiophene, 1-phenyl-indole, deuterium-substituted 1,1′-dimethyl-indene, deuterium-substituted benzofuran, deuterium-substituted benzothiophene, or deuterium-substituted 1-phenyl-indole ring, and the rest of R 4 are hydrogen or deuterium;

n1, n2, and n3 are each independently 0 or 1; and

n4 is an integer of 1 to 4,

provided that at least one of Ar is phenyl substituted with five deuteriums, or the compound of Chemical Formula 1 is substituted with at least four deuterium;

wherein the light emitting layer further comprises a compound of the following Chemical Formula 2:

wherein in the Chemical Formula 2:

Ar 1 and Ar 2 are independently substituted or unsubstituted C 6-60 aryl or substituted or unsubstituted C 5-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S;

R 7 and R 8 are each independently hydrogen, deuterium, halogen, cyano, nitro, amino, substituted or unsubstituted C 1-60 alkyl, substituted or unsubstituted C 3-60 cycloalkyl, substituted or unsubstituted C 2-60 alkenyl, substituted or unsubstituted C 6-60 aryl, or substituted or unsubstituted C 5-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S; and

p and q are each independently an integer of 0 to 7.

5 . The organic light emitting device of claim 4 , wherein Ar 1 and Ar 2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl.

6 . The organic light emitting device of claim 4 , wherein the compound of Chemical Formula 2 is any one compound selected from the group consisting of the following compounds:

7 . The organic light emitting device of claim 1 , wherein the compound of Chemical Formula 1 is the following Chemical Formula 1-1 or Chemical Formula 1-2:

wherein in the Chemical Formulae 1-1 and 1-2:

X, Y, Ar, R 1 , R 2 , R 3 , n1, n2, and n3 are as defined in claim 1 ;

A is a benzene ring;

Z is C(R 5 ) 2 , O, S, or N—(R 6 );

each R 5 is independently a C 1-10 alkyl that is unsubstituted or substituted with deuterium, or a C 6-20 aryl that is unsubstituted or substituted with deuterium;

R 6 is a C 6-60 aryl that is unsubstituted or substituted with deuterium;

R′ and R″ are each independently hydrogen or deuterium;

m1 is an integer of 1 to 4; and

m2 is an integer of 1 to 6,

provided that at least one of Ar is phenyl substituted with five deuteriums, or at least one of R 1 , R 2 , R 3 , R′, and R″ is deuterium.

8 . The organic light emitting device of claim 1 , wherein the compound of Chemical Formula 1 is any one compound selected from among the following compounds:

9 . The organic light emitting device of claim 4 , wherein the compound of Chemical Formula 1 is the following Chemical Formula 1-1 or Chemical Formula 1-2:

wherein in the Chemical Formulae 1-1 and 1-2:

X, Y, Ar, R 1 , R 2 , R 3 , n1, n2, and n3 are as defined in claim 4 ;

A is a benzene ring;

Z is C(R 5 ) 2 , O, S, or N—(R 6 );

each R 5 is independently a C 1-10 alkyl that is unsubstituted or substituted with deuterium, or a C 6-20 aryl that is unsubstituted or substituted with deuterium;

R 6 is a C 6-60 aryl that is unsubstituted or substituted with deuterium;

R′ and R″ are each independently hydrogen or deuterium;

m1 is an integer of 1 to 4; and

m2 is an integer of 1 to 6,

provided that at least one of Ar is phenyl substituted with five deuteriums, or at least one of R 1 , R 2 , R 3 , R′, and R″ is deuterium.

10 . The organic light emitting device of claim 4 , wherein the compound of Chemical Formula 1 is any one compound selected from among the following compounds:

11 . The organic light emitting device of claim 4 , wherein each X is N.

12 . The organic light emitting device of claim 9 , wherein each R 5 is methyl or phenyl.

13 . The organic light emitting device of claim 9 , wherein each R 6 is phenyl.

14 . The organic light emitting device of claim 7 , wherein each R 5 is methyl or phenyl.

15 . The organic light emitting device of claim 7 , wherein each R 6 is phenyl.