IP Library Granted Patent US 12696681
Granted Patent B2
US 12696681 · App. 17/744,164 · Granted Jul 28, 2026

Light-emitting element and aromatic compound for the same

Inventors: Heechoon Ahn (Seoul, KR); Juhui Yun (Suwon-si, KR); Hyunah Um (Seoul, KR); Yeseul Lee (Busan, KR); Seowon Cho (Asan-si, KR); Jiyong Choi (Cheonan-si, KR)
Assignee: Samsung Display Co., Ltd.
H10K85/40C07F7/0812C07F7/30C09K11/06H10K85/30C09K2211/1018C09K2211/1059C09K2211/188H10K50/11H10K50/16H10K85/626H10K85/654H10K85/6572H10K2101/10H10K2101/30
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Quick Facts
Patent No.
US 12696681
App. No.
17/744,164
Granted
Jul 28, 2026
Kind
B2
Abstract

A light-emitting that includes a first electrode, a second electrode on the first electrode, and at least one functional layer between the first electrode and the second electrode is provided. At least one functional layer may include an aromatic compound represented by Formula 1. The light-emitting element results in a reduced driving voltage and an improved luminous efficiency.

Claims (68)

1 . A light-emitting element comprising:

a first electrode;

a second electrode on the first electrode; and

at least one functional layer between the first electrode and the second electrode and including an aromatic compound represented by Formula 1:

wherein in Formula 1,

X 0 is Si or Ge,

n1 to n4 are each independently 1 or 2,

L 1 to L 4 are each independently a substituted or unsubstituted divalent hydrocarbon ring group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 3 to 30 ring-forming carbon atoms,

two selected groups from among Ar 1 to Ar 4 are nitrogen-containing heterocyclic groups and the other two groups are each a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,

n1 and n2 are 1, and L 1 and L 2 are each independently a substituted or unsubstituted divalent hydrocarbon ring group having 7 to 30 ring-forming carbon atoms if Ar 1 and Ar 2 are heterocyclic groups containing at least one nitrogen atom as a ring-forming atom, and

wherein the two nitrogen-containing heterocyclic groups are each independently a substituted pyridine group, a substituted pyrimidine group, a substituted triazine group, or a substituted quinazoline group, wherein the substituted pyridine group, the substituted pyrimidine group, or the substituted quinazoline group comprises, as a substituent, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted pyridine group.

2 . The light-emitting element of claim 1 , wherein, among the substituent, the substituted phenyl group, the substituted naphthyl group, the substituted biphenyl group, or the substituted pyridine group is substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, a oxy group, a thiol group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkenyl group, an alkynyl group, an alkoxy group, a hydrocarbon ring group, an aryl group, and a heterocyclic group.

3 . The light-emitting element of claim 1 , wherein the two nitrogen-containing heterocyclic groups are each independently represented by any one of W1-1 to W1-4 below:

wherein

in W1-1, a1 is an integer of 1 to 4,

in W1-2, a2 is an integer of 1 to 3,

in W1-3, a3 is an integer of 1 to 2,

in W1-4, a4 is an integer of 1 to 5, and

in W1-1 to W1-4, R 1 to R 4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted pyridine group.

4 . The light-emitting element of claim 1 , wherein Formula 1 is represented by any one of Formulas 2-1 to 2-3:

wherein

in Formula 2-1,

Q 1 and Q 2 are each independently CH or N and

in Formulas 2-1 to 2-3,

W 1 and W 2 are each independently the nitrogen-containing heterocyclic group,

Ar 12 to Ar 14 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and

L 2 to L 4 , n2 to n4, and X 0 are the same as defined in claim 1 .

5 . The light-emitting element of claim 4 , wherein in Formulas 2-1 to 2-3, W 1 and W 2 are the same.

6 . The light-emitting element of claim 4 , wherein in Formula 2-1, L 2 and L 4 are the same.

7 . The light-emitting element of claim 1 , wherein Formula 1 is represented by Formula 3:

wherein in Formula 3,

W 1 and W 2 are each independently the nitrogen-containing heterocyclic group,

Ar 12 and Ar 14 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and

L 2 , L 4 , n2, n4, and X 0 are the same as defined in claim 1 .

8 . The light-emitting element of claim 1 , wherein

L 1 to L 4 are each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted pyridylene group, or a substituted or unsubstituted naphthylene group.

9 . The light-emitting element of claim 1 , wherein the at least one functional layer comprises a light-emitting layer, a hole transport region between the first electrode and the light-emitting layer, and an electron transport region between the light-emitting layer and the second electrode, and

at least one of the light-emitting layer or the electron transport region includes the aromatic compound.

10 . The light-emitting element of claim 9 , wherein

the electron transport region comprises a hole blocking layer on the light-emitting layer, an electron transport layer on the hole blocking layer, and an electron injection layer on the electron transport layer, and

at least one of the hole blocking layer, the electron transport layer, or the electron injection layer includes the aromatic compound.

11 . The light-emitting element of claim 1 , wherein the aromatic compound is represented by any one of compounds of Compound Group 1:

12 . An aromatic compound represented by Formula 1:

wherein in Formula 1,

X 0 is Si or Ge,

n1 to n4 are each independently 1 or 2,

L 1 to L 4 are each independently a substituted or unsubstituted divalent hydrocarbon ring group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 3 to 30 ring-forming carbon atoms,

two selected groups from among Ar 1 to Ar 4 are nitrogen-containing heterocyclic groups and the other two groups are each a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,

n1 and n2 are 1, and L 1 and L 2 are each independently a substituted or unsubstituted divalent hydrocarbon ring group having 7 to 30 ring-forming carbon atoms if Ar 1 and Ar 2 are heterocyclic groups containing at least one nitrogen atom as a ring-forming atom, and

wherein the two nitrogen-containing heterocyclic groups are each independently a substituted pyridine group, a substituted pyrimidine group, a substituted triazine group, or a substituted quinazoline group, wherein the substituted pyridine group, the substituted pyrimidine group, or the substituted quinazoline group comprises, as a substituent, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted pyridine group.

13 . The aromatic compound of claim 12 , wherein, among the substituent, the substituted phenyl group, the substituted naphthyl group, the substituted biphenyl group, or the substituted pyridine group is substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, a oxy group, a thiol group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkenyl group, an alkynyl group, an alkoxy group, a hydrocarbon ring group, an aryl group, and a heterocyclic group.

14 . The aromatic compound of claim 12 , wherein the two nitrogen-containing heterocyclic groups are each independently represented by any one of W1-1 to W1-4 below:

wherein

in W1-1, a1 is an integer of 1 to 4,

in W1-2, a2 is an integer of 1 to 3,

in W1-3, a3 is an integer of 1 to 2,

in W1-4, a4 is an integer of 1 to 5, and

in W1-1 to W1-4, R 1 to R 4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted pyridine group.

15 . The aromatic compound of claim 12 , wherein Formula 1 is represented by any one of Formulas 2-1 to 2-3:

wherein

in Formula 2-1, Q 1 and Q 2 are each independently CH or N

in Formulas 2-1 to 2-3,

W 1 and W 2 are each independently the nitrogen-containing heterocyclic group and,

Ar 12 to Ar 14 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and

L 2 to L 4 , n2 to n4, and X 0 are the same as defined in claim 1 .

16 . The aromatic compound of claim 15 , wherein in Formulas 2-1 to 2-3, W 1 and W 2 are same.

17 . The aromatic compound of claim 12 , wherein L 1 to L 4 are each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted pyridylene group, or a substituted or unsubstituted naphthylene group.

18 . An aromatic compound, wherein the aromatic compound is represented by any one of compounds of Compound Group 1: