IP Library › Granted Patent US 11,685,751
Granted Patent B2
US 11,685,751 · App. 17/428,851 · Granted Jun 27, 2023

Compound and organic light-emitting element comprising same

Inventors: Sujeong Geum (Daejeon, KR); Hye Min Cho (Daejeon, KR); Seonwoo Kim (Daejeon, KR); Wanpyo Hong (Daejeon, KR); Jaegoo Lee (Daejeon, KR); Hoon Jun Kim (Daejeon, KR)
Assignee: LG CHEM, LTD.
H01L51/008C07F5/027C09K11/06C07B2200/05C09K2211/1018H01L51/5016H01L51/5028H01L2251/5384
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Quick Facts
Patent No.
US 11,685,751
App. No.
17/428,851
Granted
Jun 27, 2023
Kind
B2
Abstract

A compound of Chemical Formula 1, and an organic light emitting device including the same, the compound used as a material of an organic material layer of the organic light emitting device and providing high color purity and enhanced lifetime properties.

Claims (53)

1. A compound represented by the following Chemical Formula 1:

wherein in Chemical Formula 1,

X1 is O or S,

A1 is a substituted or unsubstituted heteroring; a substituted or unsubstituted aromatic hydrocarbon ring; or a substituted or unsubstituted fused ring of aromatic hydrocarbon ring and aliphatic hydrocarbon ring,

A2 is a substituted or unsubstituted aliphatic hydrocarbon ring; or a substituted or unsubstituted fused ring of aromatic hydrocarbon ring and aliphatic hydrocarbon ring having 6 to 30 carbon atoms,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted fused ring group of aromatic hydrocarbon ring and aliphatic hydrocarbon ring,

R1 is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic hydrocarbon ring and aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group,

r1 is an integer of 1 to 3,

when r1 is 2 or greater, the two or more R1s are the same as or different from each other,

the compound of Chemical Formula 1 includes at least one fused aliphatic hydrocarbon ring having 6 to 10 carbon atoms substituted with a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

2. The compound of claim 1 , wherein the compound of Chemical Formula 1 is represented by the following Chemical Formula 1-3 or 1-4:

wherein in Chemical Formulae 1-3 and 1-4,

X1, A2, Ar1, Ar2, R1 and r1 are the same as defined in Chemical Formula 1,

A″1 is a substituted or unsubstituted aliphatic hydrocarbon ring,

R11 and R12 are the same as or different from each other, and each independently hydrogen; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or adjacent groups bond to each other to form a substituted or unsubstituted ring,

r11 is an integer of 1 to 4, and when r11 is 2 or greater, the two or more R11s are the same as or different from each other, and

r12 is 1 or 2, and when r12 is 2, the two R12s are the same as or different from each other.

3. The compound of claim 2 , wherein the compound of Chemical Formula 1-4 is represented by the following Chemical Formula 1-4-1 or 1-4-2:

wherein in Chemical Formulae 1-4-1 and 1-4-2,

X1, A2, Ar1, Ar2, R1 and r1 are the same as defined in Chemical Formula 1,

A″1 is a substituted or unsubstituted aliphatic hydrocarbon ring,

R12 is hydrogen; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

r12 is 1 or 2, and when r12 is 2, the two R12s are the same as or different from each other.

4. The compound of claim 1 , wherein the compound of Chemical Formula 1 includes at least one monocyclic or polycyclic fused aliphatic hydrocarbon ring having 3 to 10 carbon atoms substituted with a linear or branched alkyl group having 1 to 30 carbon atoms unsubstituted or substituted with deuterium.

5. The compound of claim 1 , wherein A1 is a substituted or unsubstituted monocyclic or polycyclic heteroring having 2 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted fused ring of monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms,

A2 is a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted fused ring of monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 30 carbon atoms,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms; or a substituted or unsubstituted fused ring group of monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, and

R1 is hydrogen; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted amine group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted fused ring group of monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

6. A compound selected from the followings:

wherein,

Ph is a phenyl group, and D is deuterium.

7. An organic light emitting device comprising:

a first electrode;

a second electrode; and

an organic material layer including one or more layers provided between the first electrode and the second electrode,

wherein the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following Chemical Formula 1 as a dopant material, and two or more types of compounds represented by the following Chemical Formula H as the host compound:

in Chemical Formula 1,

X1 is O or S,

A1 is a substituted or unsubstituted heteroring; a substituted or unsubstituted aromatic hydrocarbon ring; or a substituted or unsubstituted fused ring of aromatic hydrocarbon ring and aliphatic hydrocarbon ring;

A2 is a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a substituted or unsubstituted fused ring of aromatic hydrocarbon ring and aliphatic hydrocarbon ring;

Ar1 and Ar2 are the same as or different from each other; and each independently a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted fused ring group of aromatic hydrocarbon ring and aliphatic hydrocarbon ring;

R1 is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted fused ring group of aromatic hydrocarbon ring and aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic group;

r1 is an integer of 1 to 3;

when r1 is 2 or greater, the two or more R1s are the same as or different from each other; and

the compound of Chemical Formula 1 includes at least one fused aliphatic hydrocarbon ring substituted with a substituted or unsubstituted alkyl group,

wherein in Chemical Formula H,

L20 and L21 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

Ar20 and Ar21 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

R20 and R21 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

r21 is an integer of 1 to 7, and when r21 is 2 or greater, the two or more R21s are the same as or different from each other.

8. The organic light emitting device of claim 7 , wherein the compound of Chemical Formula 1 is any one selected from the following compounds:

wherein,

Ph is a phenyl group, and D is deuterium.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 5, 2021
From: GEUM, SUJEONG; CHO, HYE MIN; KIM, SEONWOO; HONG, WANPYO; LEE, JAEGOO; KIM, HOON JUN
To: LG CHEM, LTD.
Reel/Frame 057094/0698 →
Priority Claims (2)
KR 10-2019-0156840 · Nov 29, 2019 · national
KR 10-2020-0060630 · May 20, 2020 · national
Continuity (1)
Related Publication 20230061019A1 · Mar 2, 2023
Cited By (2)
US 12,421,449 US 12,501,825