Organic electroluminescent materials and devices

• US 9,590,180 B2
• Filed: 09/19/2014
• Issued: 03/07/2017
• Est. Priority Date: 06/23/2007
• 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): CLARK, GREGORY D
• Application Number:
  US14/491,280
• Publication Number:
  US 20150001524A1
• Time in Patent Office: 900 Days
• Field of Search: None
• 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: 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

Disclosed is a compound having substructure F:

wherein R′₁ is a straight or branched chain of two or more non-fused aryl or non-fused heteroaryl groups substituted with R_a, wherein R_a is a non-fused aryl or non-fused heteroaryl, a branched or straight chain of non-fused aryl or a non-fused heteroaryl, or an alkyl substituted non-fused aryl or an alkyl substituted non-fused heteroaryl group. The compounds may be useful in phosphorescent organic light emitting devices.

Claims

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

2. The compound of claim 1, wherein at least two of R₁, R₂, and R₃ is a non-fused aryl or heteroaryl six-membered ring 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.

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

4. The compound of claim 1, wherein the compound has the structure:

11. The compound of claim 1, wherein at least one of R₁, R₂, and R₃ is a heteroaryl six-membered ring selected from the group consisting of pyridine, pyrazine and pyrimidine, wherein said heteroaryl six-membered ring has at least one meta-substituent that is a non-fused aryl or heteroaryl group further substituted with one or more non-fused aryl or heteroaryl groups, wherein the at least one meta-substituent is substituted with a chain of at least two non-fused aryl or heteroaryl groups.

5. A compound comprising the substructure F:

6. The compound of claim 5, wherein R_a is a branched or straight chain of non-fused aryls or heteroaryls, or an alkyl substituted non-fused aryl or an alkyl substituted non-fused heteroaryl group.

7. The compound of claim 5,

wherein R′

₁ is a straight or branched chain of two or more non-fused aryl groups substituted with R_a or a straight or branched chain of two or more non-fused heteroaryl groups substituted with R_a.

8. The compound of claim 5, wherein the compound is any one of:

9. 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;

10. The organic light emitting device of claim 9, wherein at least one of R₁, R₂, and R₃ is a heteroaryl six-membered ring selected from the group consisting of pyridine, pyrazine and pyrimidine, wherein said heteroaryl six-membered ring has at least one meta-substituent that is a non-fused aryl or heteroaryl group further substituted with one or more non-fused aryl or heteroaryl groups, wherein the at least one meta-substituent is substituted with a chain of at least two non-fused aryl or heteroaryl groups.