Syntheses, characterizations, and applications of heli-acenes

Patent metadata

Field	Value
Publication number	US-11319266-B2
Application number	US-202016867931-A
Country	US
Kind code	B2
Filing date	May 6, 2020
Priority date	May 6, 2019
Publication date	May 3, 2022
Grant date	May 3, 2022

Abstract

A method is provided for using twisted acenes, and more particularly to configurationally stable twisted acenes that are imbedded into the structure of [7]helicene at the fulcrum ring to form useable material structures. The helicene propagates its chiral nature into the acene, while acting as a locking mechanism to thermal racemization. These doubly-helical compounds are part of a new homologous series of polycyclic aromatic hydrocarbons, namely the [7]helitwistacenes. Such [7]helitwistacenes have utility as materials suitable for forming a circularly polarized organic light emitting diode (CP-OLED) for direct emission of circularly polarized (CP) light for the fabrication of high efficiency electronic displays.

First claim

The invention claimed is:

1. A heli-twisted acene selected from the group consisting of:

wherein n is 1-3, and X is simultaneously CN, Me or Ph.

2. The heli-twisted acene of claim 1 wherein the heli-twisted acene is at least one of a hole transport layer and an emissive layer of a mulit-layer organic light emitting diode (OLED).

3. The heli-twisted acene of claim 2 wherein the OLED is a circularly polarized OLED.

4. The heli-twisted acene of claim 2 wherein the OLED is a biomedical device.

5. The heli-twisted acene of claim 1 wherein the acene core is highly flurorescent.

6. The heli-twisted acene of claim 1 wherein the acene core has an end to end twist of any of 30°, 60°, and 144°.

7. The heli-twisted acene of claim 1 wherein the acene core has a specific rotation [∝] n 35 32 7400°.

8. The heli-twisted acene of claim 2 wherein the acene core is longitudinally twisted.

9. The heli-twisted acene of claim 2 wherein the heli-twisted acene is a carbocyclic heli-acene.

10. The heli-twisted acene of claim 1 wherein X in every instance is cyano.

11. The heli-twisted acene of claim 1 wherein X in every instance is methyl.

12. The heli-twisted acene of claim 1 wherein X in every instance is phenyl.

13. A process for synthesizing the heli-twisted acene of claim 2 , the process comprising:
performing a bis-Wittig reaction with a 2,8-dibromophenanthrene-5,6-dione to form an intermediate; and
then reacting the intermediate with styene in the presence of a Pd catalysis to synthesize the heli-twisted acene.

Assignees

• Univ Wyoming
• Univ Of Wyoming Office Of Research & Economic Development

Inventors

• Clennan Edward L
• Weber Jacob

Classifications

• H10K59/8793

  Arrangements for polarized light emission (H10K59/8791 takes precedence) · CPC title

• C07C15/20 Primary

  Polycyclic condensed hydrocarbons · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07C2603/54

  containing more than five condensed rings · CPC title

• C07B2200/09

  Geometrical isomers · CPC title