IP Library Granted Patent US 12677587
Granted Patent B2
US 12677587 · App. 18/148,324 · Granted Jul 7, 2026

Light emitting element and organometallic compound for the same

Inventors: Eunyoung Lee (Sejong-si, KR); Iljoon Kang (Icheon-si, KR); Soo-Byung Ko (Yongin-si, KR); Sungbum Kim (Yongin-si, KR); Sujin Shin (Yongin-si, KR); Mina Jeon (Hwaseong-si, KR)
Assignee: Samsung Display Co., Ltd.
H10K85/341C07F15/006C09K11/06H10K85/40C09K2211/1044C09K2211/1059C09K2211/185H10K50/12H10K2101/90
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Quick Facts
Patent No.
US 12677587
App. No.
18/148,324
Granted
Jul 7, 2026
Kind
B2
Abstract

A light emitting element that includes a first electrode, a second electrode on the first electrode, and an emission layer between the first electrode and the second electrode is provided. The emission layer includes an organometallic compound represented by Formula 1. The light emitting element has a reduced driving voltage, emits light having an increased color purity, and exhibits a high efficiency and a long lifespan.

Claims (71)

1 . A light emitting element comprising:

a first electrode;

a second electrode on the first electrode; and

an emission layer between the first electrode and the second electrode, and comprising an organometallic compound represented by Formula 1:

wherein in Formula 1,

Y 10 to Y 12 , Y 20 to Y 22 , and Y 30 to Y 32 are each independently C or N,

ring groups A10 to A30 are each independently a substituted or unsubstituted hydrocarbon ring group having 5 to 60 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 ring-forming carbon atoms,

a1 to a3 are each independently an integer from 0 to 3,

L 1 to L 3 are each independently a direct linkage, O, S, —C(R a11 )(R a12 )—, —C(R a13 )═, —C(R a14 )═C(R a15 )—, —C≡C—, —C(═O)—, —C(═S)—, —B(R a16 )—, —N(R a17 )—, —P(R a18 )—, —Si(R a19 )(R a20 )—, or —Ge(R a21 )(R a22 )—,

b1 to b3 are each independently an integer from 0 to 8,

b5 is an integer from 0 to 6, and

R 1 to R 5 and R a11 to R a22 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, an amidino group, a sulfinyl group, a sulfonyl group, a carbonyl group, a phosphine group, a phosphine oxide group, a phosphine sulfide group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 ring-forming carbon atoms, and/or bonded to an adjacent group to form a ring.

2 . The light emitting element of claim 1 , wherein Formula 1 is represented by Formula 2:

wherein in Formula 2,

R 11 to R 13 , R 21 to R 24 , and R 31 to R 33 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, an amidino group, a sulfinyl group, a sulfonyl group, a carbonyl group, a phosphine group, a phosphine oxide group, a phosphine sulfide group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 ring-forming carbon atoms, and/or bonded to an adjacent group to form a ring, and

a1 to a3, L 1 to L 3 , b5, R 4 , and R 5 are the same as defined in Formula 1.

3 . The light emitting element of claim 2 , wherein Formula 2 is represented by Formula 3:

wherein in Formula 3,

a1 to a3, L 1 to L 3 , b5, R 4 , R 5 , R 11 , R 21 to R 24 , and R 31 to R 33 are the same as defined in Formula 2.

4 . The light emitting element of claim 1 , wherein in Formula 1, L 1 and L 3 are each independently a direct linkage, and L 2 is O.

5 . The light emitting element of claim 1 , wherein in Formula 1, R 1 to R 5 are each independently a hydrogen atom, a deuterium atom, a dimethylamine group, a trimethylsilyl group, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted i-butyl group, a substituted or unsubstituted t-butyl group, or a substituted or unsubstituted phenyl group.

6 . The light emitting element of claim 1 , wherein in Formula 1, R 1 to R 5 are each independently represented by any one selected from among R-1 to R-10:

wherein in R-2 and R-6,

D is a deuterium atom,

wherein in R-10,

b70 is an integer from 0 to 5, and

R 70 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

7 . The light emitting element of claim 1 , wherein in Formula 1, one or more of R 1 to R 5 comprise a deuterium atom or a substituent containing a deuterium atom.

8 . The light emitting element of claim 1 , wherein the emission layer comprises a hole transporting host, an electron transporting host, and a dopant,

the dopant containing the organometallic compound.

9 . The light emitting element of claim 8 , wherein the hole transporting host comprises a compound represented by Formula HT-1, and the electron transporting host comprises a compound represented by Formula ET-1:

wherein in Formula HT-1,

a10 is an integer from 0 to 8, and

R 100 and R 101 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms;

wherein in Formula ET-1,

one or more of Y 51 to Y 53 is N and the Y 51 to Y 53 that are not N are each independently CR a ,

R a is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms,

e1 to e3 are each independently an integer from 0 to 10,

L 51 to L 53 are each independently a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms, and

Ar 1 to Ar 3 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 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.

10 . The light emitting element of claim 8 , wherein the dopant further comprises a delayed fluorescent compound.

11 . The light emitting element of claim 1 , wherein the organometallic compound is represented by any one selected from among compounds of Compound Group 1:

wherein in Compound Group 1, D is a deuterium atom.

12 . An organometallic compound represented by Formula 1:

wherein in Formula 1,

Y 10 to Y 12 , Y 20 to Y 22 , and Y 30 to Y 32 are each independently C or N,

ring groups A10 to A30 are each independently a substituted or unsubstituted hydrocarbon ring group having 5 to 60 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 ring-forming carbon atoms,

a1 to a3 are each independently an integer from 0 to 3,

L 1 to L 3 are each independently a direct linkage, O, S, —C(R a11 )(R a12 )—, —C(R a13 )═, —C(R a14 )═C(R a15 )—, —C≡C—, —C(═O)—, —C(═S)—, —B(R a16 )—, —N(R a17 )—, —P(R a18 )—, —Si(R a19 )(R a20 )—, or —Ge(R a21 )(R a22 )—,

b1 to b3 are each independently an integer from 0 to 8,

b5 is an integer from 0 to 6, and

R 1 to R 5 and R a11 to R a22 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, an amidino group, a sulfinyl group, a sulfonyl group, a carbonyl group, a phosphine group, a phosphine oxide group, a phosphine sulfide group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 ring-forming carbon atoms, and/or bonded to an adjacent group to form a ring.

13 . The organometallic compound of claim 12 , wherein Formula 1 is represented by Formula 2:

wherein in Formula 2,

R 11 to R 13 , R 21 to R 24 , and R 31 to R 33 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, an amidino group, a sulfinyl group, a sulfonyl group, a carbonyl group, a phosphine group, a phosphine oxide group, a phosphine sulfide group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 ring-forming carbon atoms, and/or bonded to an adjacent group to form a ring, and

a1 to a3, L 1 to L 3 , b5, R 4 , and R 5 are the same as defined in Formula 1.

14 . The organometallic compound of claim 13 , wherein Formula 2 is represented by Formula 3:

wherein in Formula 3,

a1 to a3, L 1 to L 3 , b5, R 4 , R 5 , R 11 , R 21 to R 24 , and R 31 to R 33 are the same as defined in Formula 2.

15 . The organometallic compound of claim 12 , wherein in Formula 1, L 1 and L 3 are each independently a direct linkage, and L 2 is O.

16 . The organometallic compound of claim 12 , wherein in Formula 1, R 1 to R 5 are each independently a hydrogen atom, a deuterium atom, a dimethylamine group, a trimethylsilyl group, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted i-butyl group, a substituted or unsubstituted t-butyl group, or a substituted or unsubstituted phenyl group.

17 . The organometallic compound of claim 12 , wherein in Formula 1, R 1 to R 5 are each independently represented by any one selected from among R-1 to R-10:

wherein in R-2 and R-6,

D is a deuterium atom,

wherein in R-10,

b70 is an integer from 0 to 5, and

R 70 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

18 . The organometallic compound of claim 12 , wherein in Formula 1, one or more of R 1 to R 5 comprise a deuterium atom or a substituent containing a deuterium atom.

19 . The organometallic compound of claim 12 , wherein in Formula 1, one or more of R 1 to R 5 comprise a t-butyl group or a substituent containing a t-butyl group.

20 . The organometallic compound of claim 12 , wherein Formula 1 is represented by any one selected from among compounds of Compound Group 1:

wherein in Compound Group 1, D is a deuterium atom.