Single triphenylene chromophores in phosphorescent light emitting diodes

• US 8,652,652 B2
• Filed: 08/07/2008
• Issued: 02/18/2014
• Est. Priority Date: 08/08/2007
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Brooks, Jason, Xia, Chuanjun, Kwong, Raymond, Fiordeliso, James
• Primary Examiner(s): Wilson, Michael H
• Application Number:
  US12/865,628
• Publication Number:
  US 20110084599A1
• Time in Patent Office: 2,021 Days
• Field of Search: None
• US Class Current: 428/690
• 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: 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 2101/30 Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
• CPC Class Codes: H10K 2101/40 Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/12 comprising dopants
• 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 85/631 : 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: Y02E 10/549 : Organic PV cells

Abstract

Novel triphenylene compounds are provided. Specific examples include multi-aryl-substituted triphenylenes. A preferred group of compounds are triphenylenes that are substituted with a non-fused aryl group having one or more meta-substituents, where each meta-substituent is a non-fused aryl group optionally substituted with further substituents selected from the group consisting of non-fused aryl groups and alkyl groups. A further preferred group of compounds are triphenylenes that are substituted with a non-fused heteroaryl group having one or more meta-substituents, where each meta-substituent is a non-fused aryl or heteroaryl group optionally substituted with further substituents selected from the group consisting of non-fused aryl groups, non-fused heteroaryl groups, and alkyl groups. Some high triplet energy analogs are expected to work with deep blue phosphorescent dopants. The compounds may be useful in phosphorescent organic light emitting devices. Also provided is an organic electroluminescent device comprising an anode, a cathode, and an emissive layer between the anode and the cathode, the emissive layer comprising a phosphorescent material and a compound having a repeat unit, the repeat unit containing a triphenylene moiety.

Claims

1. A compound comprising a triphenylene core of Formula I:

2. The compound of claim 1, wherein at least one meta-substituent is substituted with a chain of at least two non-fused aryl or heteroaryl groups.

3. The compound of claim 1, wherein at least two of R₁, R₂, and R₃ is a non-fused aryl or heteroaryl group having at least one meta-substituent that is a non-fused aryl or heteroaryl group optionally substituted with further substituents selected from the group consisting of non-fused aryl groups, non-fused heteroaryl groups, and alkyl groups.

4. The compound of claim 1, wherein each of R₁, R₂, and R₃ includes no more than three para-substituted phenyl rings.

5. The compound of claim 1 having no more than three para-substituted phenyl rings including the phenyl rings of the triphenylene core.

6. The compound of claim 1, wherein each of R₁, R₂, and R₃ is independently a hydrogen or a non-fused aryl group having one or more meta-substituents,

wherein each meta-substituent is a non-fused aryl group optionally substituted with further substituents selected from the group consisting of non-fused aryl groups and alkyl groups, and

wherein at least one of R₁, R₇ and R₃ is a non-fused aryl group having at least one meta-substituent that is a non-fused aryl further substituted with one or more non-fused aryl groups.

7. The compound of claim 1, wherein the compound is:

8. The compound of claim 1 comprising any one of substructures F—

O;

9. The compound of claim 8 having substructure F:

10. The compound of claim 9, wherein the compound is any one of:

11. The compound of claim 8 having substructure F:

12. The compound of claim 11, wherein R′

₁ is a non-fused aryl or heteroaryl group substituted with two alkyl substituted phenyl groups.

13. The compound of claim 12, wherein the compound is:

14. A compound of selected from the group consisting of:

15. The compound of claim 14, wherein the compound is selected from the group consisting of:

16. An organic light emitting device, comprising:

an anode;

a cathode;

an organic layer, disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a triphenylene core of Formula I;