Organic electroluminescent materials and devices

• US 9,577,200 B2
• Filed: 08/28/2015
• Issued: 02/21/2017
• 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:
  US14/838,450
• Publication Number:
  US 20150372243A1
• Time in Patent Office: 543 Days
• US Class Current: 1/1
• 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 a structure selected from the group consisting of:

2. The compound of claim 1, wherein X is O.

3. The compound of claim 1, wherein X is S.

4. The compound of claim 1, wherein each of R₁ to R₉ is aryl, heteroaryl, or no substitution.

5. The compound of claim 1, wherein at least one R₁, R₂, R₃, or R₄ is other than hydrogen.

6. The compound of claim 1,

wherein at least one R₅ is other than hydrogen, and

wherein the structure is selected from the group consisting of Compound 1G to Compound 30G and Compound 32G to Compound 48G.

7. The compound of claim 1,

wherein at least one R₆ is other than hydrogen, and

wherein the compound has a structure is selected from the group consisting of Compound 2G, Compound 3G, Compound 4G, Compound 5G, Compound 9G, Compound 10G, Compound 11G, Compound 16G, Compound 21G, Compound 22G, Compound 23G, Compound 24G, Compound 25G, Compound 26G, Compound 27G, Compound 28G, Compound 35G, Compound 36G, Compound 37G, Compound 38G, Compound 39G, Compound 40G, Compound 43G, Compound 44G, Compound 45G, Compound 46G, Compound 47G, and, Compound 48G.

8. The compound of claim 1,

wherein at least one R₆ is other than hydrogen, and

wherein the compound has a structure is selected from the group consisting of Compound 2G, Compound 3G, Compound 4G, Compound 50, Compound 9G, Compound 10G, Compound 11G, Compound 16G, Compound 21G, Compound 22G, Compound 23G, Compound 24G, Compound 25G, Compound 26G, Compound 27G, Compound 28G, Compound 35G, Compound 36G, Compound 37G, Compound 38G, Compound 39G, Compound 40G, Compound 43G, Compound 44G, Compound 45G, Compound 46G, Compound 47G, and Compound 48G.

9. The compound of claim 1,

wherein at least one R₇ is other than hydrogen, and

wherein the compound has a structure is selected from the group consisting of Compound 4G, Compound 5G, Compound 9G, Compound 10G, Compound 11G, Compound 16G, 21G, Compound 23G, Compound 25G, Compound 26G, Compound 27G, Compound 28G, Compound 37G, Compound 38G, Compound 39G, Compound 44G, and Compound 47G.

10. The compound of claim 1,

wherein at least one R₈ is other than hydrogen, and

wherein the compound has a structure is selected from the group consisting of Compound 4G, Compound 5G, Compound 27G, Compound 28G, Compound 38G, and Compound 39G.

11. The compound of claim 1,

wherein at least one R₉ is other than hydrogen, and the compound has a structure of Compound 4G.

12. The compound of claim 1, having a structure selected from the group consisting of:

13. The compound of claim 12, wherein X is O.

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

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 a structure selected from the group consisting of;

16. The organic light emitting device of claim 15, wherein the organic layer further comprises a phosphorescent emitter.

17. The organic light emitting device of claim 16, wherein the phosphorescent emitter is an iridium complex.

18. The organic light emitting device of claim 15, wherein the compound is

19. The organic light emitting device of claim 15, wherein the compound is