Disubstituted pyrene compounds with amino group containing ortho aryl group and devices containing the same

• US 9,293,712 B2
• Filed: 09/15/2014
• Issued: 03/22/2016
• Est. Priority Date: 10/11/2013
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Kwong, Raymond, Tsang, Kit Yee, Lam, Sze Kui
• Primary Examiner(s): HENRY, CALEB E
• Application Number:
  US14/486,468
• Publication Number:
  US 20150102321A1
• Time in Patent Office: 554 Days
• Field of Search: 257/40, 564/308, 564/426, 549/460
• US Class Current: 1/1
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/156 comprising a multilayered structure
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/623 containing five rings, e.g. pentacene
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• CPC Class Codes: H10K 85/636 comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6574 comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes

Abstract

Compounds according to Formula 1, devices containing the same and formulations containing the same are described. Formula 1 has the following structure:

• • where at least two of R¹—R¹⁰ are not H,
  • where at least one of R¹—R¹⁰ has the formula T1

• • where L is an organic linker,
  • where Y¹ to Y⁴ are CR or N,
  • where adjacent R moieties can form fused rings,
  • where R^s and R^t are independently aryl or heteroaryl, either of which may independently be further substituted, and
  • where R^s and R^t do not form fused rings with any part of the molecule.

Claims

1. A compound having Formula 1:

2. The compound of claim 1, wherein linker L is alkyl, aryl or heteroaryl.

3. The compound of claim 1, wherein R_s can comprise a moiety selected from the group consisting of dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-dibenzothiophene, aza-dibenzofuran, or aza-dibenzoselenophene, phenyl, pyridine, and combinations thereof.

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

5. The compound of claim 1, wherein R¹ has the formula

6. The compound of claim 1, wherein R¹ has the formula

7. The compound of claim 6, wherein the compound is selected from the group consisting of:

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

9. The compound of claim 1, wherein R¹ has the formula

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

11. A first device comprising a first organic light emitting device, the first organic light emitting device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound having Formula 1;

12. The first device of claim 11, wherein R¹ has the formula T1

13. The first device of claim 11, wherein R¹ has the formula T1

14. The first device of claim 11, wherein R¹ and R⁶ have the formula T1

15. The first device of claim 11, wherein R¹ has the formula T1

16. The first device of claim 11, wherein the first device is selected from the group consisting of a consumer product, an electronic component module, an organic light-emitting device, and a lighting panel.

17. The first device of claim 11, wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

18. The first device of claim 11, wherein the organic layer further comprises a host material;

wherein the host material contains aromatic groups selected from the group consisting of naphthalene, triphenylene, anthracene, chrysene, triazene, carbazole, dibenzofuran, dibenzothiophene, dibenzoselenophene, and various aza analogs thereof.

19. A formulation comprising a compound of Formula 1,