Benzo-fused thiophene / triphenylene hybrid materials

• US 8,822,708 B2
• Filed: 12/14/2012
• Issued: 09/02/2014
• Est. Priority Date: 08/08/2007
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Ma, Bin, Wu, Yonggang, Lin, Chun, Kwong, Raymond
• Primary Examiner(s): SHAMEEM, GOLAM M
• Application Number:
  US13/714,872
• Publication Number:
  US 20130175510A1
• Time in Patent Office: 627 Days
• Field of Search: 549/29, 549/49, 549/456, 549/462, 549/471, 428/690, 428/917, 313/504, 313/506
• US Class Current: 549/471
• CPC Class Codes: C07C 15/38 containing four rings
• CPC Class Codes: C07C 2603/42 containing only six-membered rings
• CPC Class Codes: C07D 307/91 Dibenzofurans; Hydrogenated dibenzofurans
• CPC Class Codes: C07D 333/76 Dibenzothiophenes
• CPC Class Codes: C07D 409/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C09B 57/00 Other synthetic dyes of known constitution
• CPC Class Codes: C09K 11/025 non-luminescent particle coatings or suspension media
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/12 comprising dopants
• CPC Class Codes: H10K 50/15 Hole transporting layers
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 50/18 Carrier blocking layers
• CPC Class Codes: H10K 85/141 comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
• CPC Class Codes: H10K 85/324 : comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/342 : comprising iridium
• CPC Class Codes: H10K 85/622 : containing four rings, e.g. pyrene
• 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 85/657 : Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: H10K 85/6574 : comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
• CPC Class Codes: H10K 85/6576 : comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

Triphenylene containing benzo-fused thiophene compounds are provided. Additionally, triphenylene containing benzo-fused furan compounds are provided. The compounds may be useful in organic light emitting devices, particularly as hosts in the emissive layer of such devices, or as materials for enhancement layers in such devices, or both.

Claims

1. A compound represented by the structure of Formula (IV):

2. The compound of claim 1, wherein the compound is represented by the structure of Formula (IV):

3. The compound of claim 2, wherein X is S.

4. The compound of claim 2, wherein X is O.

5. The compound of claim 2, wherein the compound is represented by the structure:

6. The compound of claim 5, wherein X is S.

7. The compound of claim 5, wherein X is O.

8. The compound of claim 1, wherein the compound is represented by the structure of Formula (V):

9. The compound of claim 8, wherein X is S.

10. The compound of claim 8, wherein X is O.

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

12. The compound of claim 11, wherein X is S.

13. The compound of claim 11, where X is O.

14. The compound of claim 1, wherein Ar₁ and Ar₂ are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, and carbazole.

15. An organic light emitting device, comprising:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound represented by the structure of Formula (IV);

16. The device of claim 15, wherein the organic layer is an emissive layer.

17. The device of claim 16, wherein the organic layer further comprises a phosphorescent emitter.

18. The device of claim 17, wherein the phosphorescent emitter is an iridium complex.

19. The device of claim 15, wherein the organic layer comprises Compound 2S and an iridium complex.

20. The device of claim 15, wherein Ar₁ and Ar₂ are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, and carbazole.