Single triphenylene chromophores in phosphorescent light emitting diodes
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.
1. A compound comprising a triphenylene core of Formula I:
wherein each of R 1 , R 2 , and R 3 is independently a hydrogen, a non-fused aryl group or a non-fused heteroaryl group having one or more meta-substituents;
wherein 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; and
wherein at least one of R 1 , R 7 and R 3 is a non-fused aryl or heteroaryl group having 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.
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 R 1 , R 2 , and R 3 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 R 1 , R 2 , and R 3 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 R 1 , R 2 , and R 3 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 R 1 , R 7 and R 3 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:
wherein each of R′ 1-6 is independently a hydrogen, a non-fused aryl group or a non-fused heteroaryl group optionally substituted with R a , wherein R a is-a non-fused aryl or heteroaryl, a branched or straight chain of non-fused aryls or heteroaryls, or alkyl substituted aryl or heteroaryl group.
9. The compound of claim 8 having substructure F:
wherein R′ 1 is a straight or branched chain of two or more non-fused aryl groups or non-fused heteroaryl groups.
10. The compound of claim 9 , wherein the compound is any one of:
11. The compound of claim 8 having substructure F:
wherein R′ 1 is a non-fused aryl or heteroaryl group substituted with at least one alkyl substituted phenyl group.
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:
wherein each of R′ 1 , R′ 2 , R′ 3 , and R′ 4 is an unsubstituted non-fused aryl or heteroaryl group.
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:
wherein each of R 1 , R 2 , and R 3 is independently a hydrogen, a non-fused aryl group or a non-fused heteroaryl group having one or more meta-substituents,
wherein 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, and
wherein at least one of R 1 , R 7 and R 3 is a non-fused aryl or heteroaryl group having 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.