THERMALLY ACTIVATED DELAYED FLUORESCENCE CHROMOPHORES AND ORGANIC LAYERS INCLUDING THE SAME

• US 20200131436A1
• Filed: 10/30/2019
• Published: 04/30/2020
• Est. Priority Date: 10/31/2018
• Status: Active Application

• Current Assignee: Wright State University
• Original Assignee: Wright State University
• Inventors: Fossum, Eric
• Application Number:
  US16/668,876
• Publication Number:
  US 20200131436A1
• Time in Patent Office: Days
• CPC Class Codes: C08G 65/40 from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
• CPC Class Codes: C08G 75/23 Polyethersulfones
• CPC Class Codes: C08L 81/06 Polysulfones; Polyethersulfones
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1018 Heterocyclic compounds

Abstract

Thermally activated delayed fluorescence chromophores may comprise a donor ligand, an acceptor ligand, and an acceptor tuner ligand. The donor ligand may be selected from one or more of carbazole, diphenylamine, phenothiazine, phenoxazine, or acridine. The acceptor ligand may be selected from one or more of benzoxazole, benzothiazole, or diphenyl sulfone. The acceptor tuner ligand may comprise a benzene ring. The benzene ring may be at least partially substituted. Organic layers, such as polymers or films, comprising the thermally activated delayed fluorescence chromophores are also disclosed.

Claims

1. A thermally activated delayed fluorescence chromophore comprising:

a donor ligand selected from one or more of carbazole, diphenylamine, phenothiazine, phenoxazine, or acridine;

an acceptor ligand selected from one or more of benzoxazole, benzothiazole, or diphenyl sulfone; and

an acceptor tuner ligand comprising a benzene ring, wherein the benzene ring is at least partially substituted.

2. The thermally activated delayed fluorescence chromophore of claim 1, wherein the donor ligand comprises carbazole comprising the structure:

3. The thermally activated delayed fluorescence chromophore of claim 1, wherein the donor ligand comprises diphenylamine comprising the structure:

4. The thermally activated delayed fluorescence chromophore of claim 1, wherein the donor ligand comprises phenothiazine comprising the structure:

5. The thermally activated delayed fluorescence chromophore of claim 1, wherein the donor ligand comprises phenoxazine comprising the structure:

6. The thermally activated delayed fluorescence chromophore of claim 1, wherein the donor ligand comprises acridine comprising the structure:

7. The thermally activated delayed fluorescence chromophore of claim 1, wherein the benzene ring is substituted with one or more functional groups selected from one or more of fluorine, chlorine, bromine, hydroxyl, thiol, nitro, nitrile, trifluoromethyl, amine, alkyl, ester, sulfonyl, sulfonamide, acyl, amide, ether, aryl, trialyklsilyl, or trialkylsiloxy.

8. The thermally activated delayed fluorescence chromophore of claim 1, wherein the benzene ring is at least partially substituted with two or more functional groups and at least two of the two or more functional groups are located at the 2 and 3 position of the benzene ring, the 2 and 4 position of the benzene ring, the 2 and 5 position of the benzene ring, or the 2 and 6 position of the benzene ring.

9. A poly(arylene ether) comprising:

a thermally activated delayed fluorescence chromophore comprising;

a donor ligand selected from one or more of carbazole, diphenylamine, phenothiazine, phenoxazine, or acridine;

an acceptor ligand selected from one or more of benzoxazole, benzothiazole, or diphenyl sulfone; and

an acceptor tuner ligand comprising a benzene ring, wherein the benzene ring is at least partially substituted with two or more functional groups; and

at least one monomer selected from one or more of 4,4′

-difluorodiphenyl sulfone, 4,4′

-difluorobenzophenone, 4,4′

-difluorotriphenylphosphine oxide, 2,5-bis(4-fluorophenyl)-1,3,4-oxadiazole, 2,3-bis(4-fluorophenyl)-quinoxaline, 2,5-bis(4-fluorophenyl)-oxazole, bisphenol-A, bisphenol-AF, 4,4′

-dihydroxybiphenyl, 4,4′

-dihydroxydiphenyl ether, hydroquinone, catchol, or resorcinol.

10. The poly(arylene ether) of claim 9, wherein the donor ligand comprises carbazole comprising the structure:

11. The poly(arylene ether) of claim 9, wherein the donor ligand comprises diphenylamine comprising the structure:

12. The poly(arylene ether) of claim 9, wherein the donor ligand comprises phenothiazine comprising the structure:

13. The poly(arylene ether) of claim 9, wherein the donor ligand comprises phenoxazine comprising the structure:

14. The poly(arylene ether) of claim 9, wherein the donor ligand comprises acridine comprising the structure:

15. The poly(arylene ether) of claim 9, wherein the two or more functional groups are selected from one or more of fluorine, chlorine, a hydroxyl group, or a thiol group.

16. The poly(arylene ether) of claim 9, wherein at least two of the two or more functional groups are located at the 2 and 3 position of the benzene, the 2 and 4 position of the benzene, the 2 and 5 position of the benzene, or the 2 and 6 position of the benzene.

17. The poly(arylene ether) of claim 9, wherein the two or more functional groups are selected from one or more of fluorine and chlorine.

18. The poly(arylene ether) of claim 17, wherein the poly(arylene ether) has the formula:

{[M₁]_x-[M₂]_1-x-M₃}_n

wherein;

M₁ is the thermally activated delayed fluorescence chromophore;

M₂ is a first monomer selected from one or more of 4,4′

-difluorodiphenyl sulfone, 4,4′

-difluorobenzophenone, 4,4′

-difluorotriphenylphosphine oxide, 2,5-bis(4-fluorophenyl)-1,3,4-oxadiazole, 2,3-bis(4-fluorophenyl)-quinoxaline, or 2,5-bis(4-fluorophenyl)-oxazole; and

M₃ is a second monomer selected from one or more of bisphenol-A, bisphenol-AF, 4,4′

-dihydroxybiphenyl, 4,4′

-dihydroxydiphenyl ether, hydroquinone, catechol, or resorcinol.

19. The poly(arylene ether) of claim 9, wherein the two or more functional groups are selected from one or more of a hydroxyl group and a thiol group.

20. The poly(arylene ether) of claim 19, wherein the poly(arylene ether) has the formula:

{[M₁]_x-[M₃]_1-x-M₂}_n

wherein;

M₁ is the thermally activated delayed fluorescence chromophore;

M₂ is a first monomer selected from one or more of 4,4′

-difluorodiphenyl sulfone, 4,4′

-difluorobenzophenone, 4,4′

-difluorotriphenylphosphine oxide, 2,5-bis(4-fluorophenyl)-1,3,4-oxadiazole, 2,3-bis(4-fluorophenyl)-quinoxaline, or 2,5-bis(4-fluorophenyl)-oxazole; and

M₃ is a second monomer selected from one or more of bisphenol-A, bisphenol-AF, 4,4′

-dihydroxybiphenyl, 4,4′

-dihydroxydiphenyl ether, hydroquinone, catechol, or resorcinol.