IP Library › Granted Patent US 11,572,346
Granted Patent B2
US 11,572,346 · App. 16/761,954 · Granted Feb 7, 2023

Compound, coating composition comprising same, and organic light-emitting device

Inventors: Kwanghyun Kim (Daejeon, KR); Youngju Park (Daejeon, KR); Sungkyoung Kang (Daejeon, KR); Jaesoon Bae (Daejeon, KR); Jaechol Lee (Daejeon, KR); Yu Jin Woo (Daejeon, KR); Daeho Kim (Daejeon, KR); Byungjae Kim (Daejeon, KR)
C07D209/86H01L51/006H01L51/008H01L51/0072H01L51/0081H01L51/5056
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Quick Facts
Patent No.
US 11,572,346
App. No.
16/761,954
Granted
Feb 7, 2023
Kind
B2
Abstract

The present specification relates to a compound, a coating composition including the same, and an organic light emitting device.

Claims (56)

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

wherein, in Chemical Formula 1,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group;

R1 to R4 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group;

r1 to r3 are the same as or different from each other, and each independently from 1 to 3;

r4 is from 1 to 4;

when r1 to r4 are each 2 or greater, the two or more R1 to R4 are the same as or different from each other;

X1 and X2 are the same as or different from each other, and each independently

each

means a linking site;

a1 is 0 or 1, a2 is an integer of 0 to 2;

when a2 is 0, L2 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted aralkyl group;

when a2 is 1, L2 is a direct bond; or a substituted or unsubstituted arylene group;

when a2 is 2, L2 is a trivalent substituted or unsubstituted aryl group;

L1 is a substituted or unsubstituted arylene group;

m is an integer of 1 or 2, and when m is 2, L1s are the same as or different from each other;

n is an integer of 1 or 2, and when n is 1, L3 is a substituted or unsubstituted arylene group, and when n is 2, L3s are the same as or different from each other, and each independently a substituted or unsubstituted arylene group and a substituted or unsubstituted alkylene group; and

0≤a1+a2≤2.

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

in Chemical Formula 2,

L1 to L3, Ar1, Ar2, R1 to R4, r1 to r4, X1, X2, m, n, a1 and a2 have the same definitions as in Chemical Formula 1.

3. The compound of claim 1 , wherein L1 and L3 are the same as or different from each other, and each independently a substituted or unsubstituted phenylene group.

4. The compound of claim 1 , wherein Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted spirobifluorene group; or a substituted or unsubstituted dibenzofuran group.

5. The compound of claim 1 , wherein the compound represented by Chemical Formula 1 is any one selected from among the following compounds:

6. A coating composition comprising the compound of claim 1 .

7. An organic light emitting device comprising:

a first electrode;

a second electrode provided opposite to the first electrode; and

at least one organic material layers provided between the first electrode and the second electrode,

wherein the at least one organic material layer includes the coating composition of claim 6 or a cured material thereof.

8. The organic light emitting device of claim 7 , wherein the cured material of the coating composition is in a cured state by heat treating or light treating the coating composition.

9. The organic light emitting device of claim 7 , wherein the at least one organic material layer including the coating composition or a cured material thereof is a hole transfer layer, a hole injection layer, or a layer carrying out hole transfer and hole injection at the same time.

10. The organic light emitting device of claim 7 , wherein the at least one organic material layer including the coating composition or a cured material thereof is a light emitting layer.

11. The organic light emitting device of claim 7 , wherein coating composition further includes an ionic compound including an anion group represented by the following Chemical Formula 11; and a cation group represented by the following Chemical Formula 12:

in Chemical Formula 11,

at least one of R101 to R120 is F; a cyano group; or a substituted or unsubstituted fluoroalkyl group;

at least one of the remaining R101 to R120 is a curing group; and

the remaining R101 to R120 if present are the same as or different from each other, and each independently hydrogen; deuterium; a nitro group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

in Chemical Formula 12,

R121 to R130 are the same as or different from each other, and each independently hydrogen; deuterium; a nitro group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or a curing group.

12. The organic light emitting device of claim 11 , wherein at least one of R103, R108, R113 and R118 is a curing group.

13. The organic light emitting device of claim 11 , wherein the curing group is any one selected from among the following structures:

in the structures,

L11 is a direct bond; —O—; —S—; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group;

k is 1 or 2;

when k is 2, L11s are the same as or different from each other;

R131 is a substituted or unsubstituted alkyl group; and

each

means a linking site.

14. The organic light emitting device of claim 11 , wherein the anion group represented by Chemical Formula 11 is any one selected from among the following structures:

15. The organic light emitting device of claim 11 , wherein the cation group represented by Chemical Formula 12 is any one selected from among the following structures:

16. The compound of claim 1 , wherein when a2 is 0, L2 is a phenyl group unsubstituted or substituted with deuterium, a halogen group, an alkyl group or an alkoxy group; a fluorene group unsubstituted or substituted with deuterium, a halogen group, an alkyl group or an alkoxy group; or a benzyl group unsubstituted or substituted with deuterium, a halogen group, an alkyl group or an alkoxy group,

when a2 is 1, L2 is a direct bond; or a phenylene group, and

when a2 is 2, L2 is a trivalent substituted or unsubstituted phenyl group.

17. The organic light emitting device of claim 11 , wherein the curing group of Chemical Formula 11 is a vinyl group.

18. The organic light emitting device of claim 11 , wherein R103, R108, R113 and R118 are the same as or different from each other, and each independently a vinyl group or F.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 7, 2020
From: KIM, KWANGHYUN; PARK, YOUNGJU; KANG, SUNGKYOUNG; BAE, JAESOON; LEE, JAECHOL; WOO, YU JIN; KIM, DAEHO; KIM, BYUNGJAE
To: LG CHEM, LTD.
Reel/Frame 052597/0047 →
Priority Claims (1)
KR 10-2018-0058329 · May 23, 2018 · national
Continuity (1)
Related Publication 20210147358A1 · May 20, 2021