IP Library Granted Patent US 11,201,290
Granted Patent B2
US 11,201,290 · App. 16/157,121 · Granted Dec 14, 2021

Tetraphenylene anthracene compounds

Inventor: Chuanjun Xia (Lawrenceville, NJ)
Assignee: BEIJING SUMMER SPROUT TECHNOLOGY CO., LTD.
H01L51/0055C07C13/62C07D209/58C07D235/08C07D251/24C07D307/91C07D333/50C07D401/04C07D471/04C07D487/04C07D491/04C07D495/04C09K11/06H01L51/0058C07C2603/24C07C2603/40C07C2603/50C07C2603/52C09K2211/1007C09K2211/1011H01L51/5012H01L51/5056H01L51/5072
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Quick Facts
Patent No.
US 11,201,290
App. No.
16/157,121
Granted
Dec 14, 2021
Kind
B2
Abstract

Novel tetraphenylene anthracene compounds are disclosed, which can be used as charge transporting materials, emitters, hosts in an organic electroluminescent device. These novel compounds offer better device performance. Also disclosed are an electroluminescent device and a formulation.

Claims (23)

1. A compound having formula 1:

wherein

X 1 to X 16 are each independently selected from the group consisting of C, CR, and N;

L is selected from the group consisting of a single bond, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 4 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms;

R 1 represents mono, multi substitution or no substitution;

R is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

R 1 is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

any adjacent substitution can be optionally joined to form a ring or fused structure.

2. The compound of claim 1 , wherein none of X 1 to X 16 is N.

3. The compound of claim 1 , wherein at least one of X 1 to X 16 is N.

4. The compound of claim 1 , wherein L is selected from the group consisting of:

and combinations thereof.

5. The compound of claim 1 , wherein R 1 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.

6. The compound of claim 1 , wherein R 1 is a substituted or unsubstituted aryl group comprising a fused ring system.

7. The compound of claim 1 , wherein R 1 is selected from the group consisting of phenyl, biphenyl, terphenyl, pyridine, pyrimidine, triazine, dibenzofuran, dibenzothiophene, carbazole, fluorene, triphenylene, phenanthrene, phenanthroline, pyrene, and combinations thereof.

8. The compound of claim 1 , wherein L is connected to the 9 th position of anthracene and R 1 is connected to the 10 th position of anthracene.

9. The compound of claim 1 , wherein the compound is selected from the group consisting of:

10. An electroluminescent device comprises an anode, a cathode, and an organic layer, disposed between the anode and the cathode, comprising the compound of claim 1 .

11. The device of claim 10 , wherein the organic layer is a charge transporting layer.

12. The device of claim 10 , wherein the organic layer is a light-emitting layer and the compound is a host.

13. The device of claim 10 , wherein the organic layer is a light-emitting layer and the compound is an emitter.

14. The device of claim 10 , wherein the organic layer further comprises a fluorescent emitter.

15. A formulation comprising the compound of claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 27, 2018
From: XIA, CHUANJUN
To: BEIJING SUMMER SPROUT TECHNOLOGY CO., LTD.
Reel/Frame 047855/0713 →
Continuity (2)
Provisional Application 62571763 · Oct 12, 2017
Related Publication 20190115541A1 · Apr 18, 2019