IP Library Granted Patent US 11,535,637
Granted Patent B2
US 11,535,637 · App. 16/643,721 · Granted Dec 27, 2022

Compound and organic light emitting element comprising same

Inventors: Hongsik Yoon (Daejeon, KR); Yujin Kang (Daejeon, KR); Wanpyo Hong (Daejeon, KR); Sang Duk Suh (Daejeon, KR)
Assignee: LG CHEM, LTD.
C07F5/02C07F5/027C09K11/06H01L51/008H01L51/0072H01L51/0073H01L51/0074H01L51/5012
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Quick Facts
Patent No.
US 11,535,637
App. No.
16/643,721
Granted
Dec 27, 2022
Kind
B2
Abstract

Provided are boron-containing polycyclic compounds of Chemical Formula 1: wherein X1 to X4 are identical to or different from one another and are each independently O, S, NR2 or CR3R4, and a to d are each 0 or 1, with the proviso that 1≤a+b+c+d, and the other substituents are as described in the specification. The compounds have a high electron accepting ability and excellent heat resistance, and can be highly purified by sublimation purification due to their high sublimation temperature. The compounds can form a stable interface with an electrode or an adjacent organic material layer of an organic light emitting device. Also provided is an organic light emitting device including the compound of Chemical Formula 1. The compound can lower driving voltage and lengthen lifetime of the organic light emitting device.

Claims (32)

1. A compound of Chemical Formula 1:

wherein X1 to X4 are identical to or different from one another and are each independently O, S, NR2 or CR3R4, and a to d are each 0 or 1, with the proviso that 1≤a+b+c+d;

R1 and R11 to R14 are identical to or different from one another and are each independently hydrogen, deuterium, a nitrile 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;

e is an integer of 0 to 3, wherein, when e is 2 or more, each R1 is identical to or different from each other;

aa, bb, cc and dd are each an integer of 0 to 4, wherein, when aa, bb, cc and dd are 2 or more, the substituents in parentheses are identical to or different from one another;

R2 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group; and

R3 and R4 are identical to or different from each other and are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

2. The compound of claim 1 , wherein Chemical Formula 1 any one of the following Chemical Formulae 2 to 7:

wherein X1 to X4, R1, R11 to R14, aa, bb, cc, dd and e are defined as in Chemical Formula 1 above.

3. The compound of claim 1 , wherein Chemical Formula 1 is any one of the following Chemical Formulae 8 to 12:

wherein X1 to X4, R1, R11 to R14, aa, bb, cc, dd and e are defined as in Chemical Formula 1 above.

4. The compound of claim 1 , wherein Chemical Formula 1 is the following Chemical Formula 1-1:

wherein X1 to X4, R1 and a to d are defined as in Chemical Formula 1 above.

5. The compound of claim 4 , wherein R1 is hydrogen, a methyl group, a tert-butyl group or a nitrile group.

6. The compound of claim 1 , wherein X1 to X4 are identical to or different from each other and each independently is O, S, NR2, or CR3R4;

R2 is an aryl group that is unsubstituted or substituted by a deuterium, a nitrile group or an alkyl group; and

R3 and R4 are each an alkyl group.

7. The compound of claim 1 , wherein the compound of Chemical Formula 1 is selected from one of the following compounds:

8. An organic light emitting device comprising:

a first electrode;

a second electrode facing the first electrode; and

at least one organic material layer interposed between the first electrode and the second electrode,

wherein the at least one organic material layer comprises the compound of claim 1 .

9. The organic light emitting device of claim 8 , wherein:

the organic material layer comprises a light emitting layer, and

the light emitting layer comprises the compound.

10. The organic light emitting device of claim 8 , wherein:

the organic material layer comprises an electron injection layer, an electron transport layer or an electron injection and transport layer, and

the electron injection layer, the electron transport layer or the electron injection and transport layer comprises the compound.

11. The organic light emitting device of claim 8 , wherein:

the organic material layer comprises a hole injection layer, a hole transport layer or a hole injection and transport layer, and

the hole injection layer, the hole transport layer or the hole injection and transport layer comprises the compound.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 2, 2020
From: YOON, HONGSIK; KANG, YUJIN; HONG, WANPYO; SUH, SANG DUK
To: LG CHEM, LTD.
Reel/Frame 051980/0230 →
Priority Claims (1)
KR 10-2017-0179561 · Dec 26, 2017 · national
Continuity (1)
Related Publication 20200216475A1 · Jul 9, 2020