Organic electroluminescent transistor

Patent metadata

Field	Value
Publication number	US-9825261-B2
Application number	US-201715414513-A
Country	US
Kind code	B2
Filing date	Jan 24, 2017
Priority date	Jul 24, 2014
Publication date	Nov 21, 2017
Grant date	Nov 21, 2017

Abstract

The present teachings relate to an organic electroluminescent transistor with improved light-emission characteristics. More specifically, the present organic electroluminescent transistor has an emissive ambipolar channel including at least one layer of an n-type semiconductor material, at least one layer of a p-type semiconductor material, and at least one layer of an emissive material arranged between the layers of the p-type and n-type semiconductor materials, with the n-type semiconductor material comprising an electron-transporting compound represented by formula (N-1):

where X, Ar, Ar′, R 1 , R 2 , m and m′ are as defined herein.

First claim

The invention claimed is:

1. An organic electroluminescent transistor comprising: at least one dielectric layer; at least one control electrode; at least one hole electrode; at least one electron electrode; and an assembly comprising an emissive ambipolar channel, wherein:
said dielectric layer is arranged between said control electrode and said assembly;
said emissive ambipolar channel comprises at least one layer of an n-type semiconductor material, at least one layer of a p-type semiconductor material, and at least one layer of an emissive material arranged between said layers of p-type and n-type semiconductor materials;
said n-type semiconductor material comprises an electron-transporting compound represented by formula (N-1):

wherein:
X is selected from the group consisting of O, S, and Se;
Ar and Ar′, at each occurrence, independently are identical or different monocyclic aryl or heteroaryl groups;
R 1 and R 2 independently are identical or different electron-withdrawing groups selected from the group consisting of —CN, R a , —C(O)R b , and —C(O)OR b ; wherein R a is a C 1-20 alkyl, C 2-20 alkenyl, or C 2-20 alkynyl group substituted with at least one fluoro or cyano group; and R b is selected from the group consisting of H, a C 1-20 alkyl group, a C 2-20 alkenyl group, and a C 2-20 alkynyl group, wherein each of the C 1-20 alkyl group, the C 2-20 alkenyl group, and the C 2-20 alkynyl group optionally is substituted with one or more fluoro and/or cyano groups; and
m and m′ independently are 1 or 2.

2. The transistor of claim 1 , wherein the electron-transporting compound is represented by formula (N-2):

3. The transistor of claim 1 , wherein the electron-transporting compound is represented by formula (N-3):

wherein n is an integer ranging from 1 to 12 (inclusive).

4. The transistor of claim 1 , wherein Ar and Ar′, at each occurrence, independently are selected from the group consisting of a phenyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a pyrrolyl group, a triazolyl group, a tetrazolyl group, a pyrazolyl group, an imidazolyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, and a pyrazinyl group.

5. The transistor of claim 4 , wherein the electron-transporting compound is represented by formula (N-4):

6. The transistor of claim 5 , wherein the electron-transporting compound is 2,5-bis(4-(perfluorooctyl)phenyl)thieno[3,2-b]thiophene (N-F2-6):

or 2,5-bis(4-(trifluoromethyl)phenyl)thieno[3,2-b]thiophene (N-F2-6-CF3):

7. The transistor of claim 1 , wherein the p-type semiconductor material comprises a hole-transporting compound selected from the group consisting of an oligothiophene, an acene, and a fused heteroarene.

8. The transistor of claim 1 , wherein the p-type semiconductor material comprises a hole-transporting compound selected from the group consisting of a dithiophene, a quaterthiophene, a thienothiophene, a benzothiophene, a naphthothiophene, a benzothieno[3,2-b][1]benzothiophene, and a dinaphtho[2,3-b:2′,3′-f]thieno[3,2-b]thiophenes, each of which can be optionally α- and/or ω-substituted with a hydrocarbon group.

9. The transistor of claim 1 , wherein the p-type semiconductor material comprises a hole-transporting compound represented by formula (P-1), (P-2), (P-3), (P-4), (P-5) or (P-6):

wherein R 3 and R 4 independently are H or identical or different C 1-20 alkyl groups.

10. The transistor of claim 9 , wherein the p-type semiconductor material comprises a hole-transporting compound selected from the group consisting of:

11. The transistor of claim 10 , wherein the emissive material is blue-emitting.

12. The transistor of claim 11 , wherein the emissive material comprises a blend of the arylamine matrix compound of formula (H-1) and the blue emitter of formula (G-1):

a blend of the arylamine matrix compound of formula (H-2) and the blue emitter of formula (G-1):

or
a blend of the arylamine matrix compound of formula (H-3) and the blue emitter of formula (G-1):

13. The transistor of claim 10 , wherein the emissive material is green-emitting.

14. The transistor of claim 13 , wherein the emissive material comprises a blend of the arylamine matrix compound of formula (H-1) and the green emitter of formula (G-2):

a blend of the arylamine matrix compound of formula (H-2) and the green emitter of formula (G-2):

or
a blend of the arylamine matrix compound of formula (H-3) and the green emitter of formula (G-2):

15. The transistor of claim 10 , wherein the emissive material is red-emitting.

16. The transistor of claim 15 , wherein the emissive material comprises a blend of the arylamine matrix compound of formula (H-1) and the red emitter of formula (G-3):

a blend of the arylamine matrix compound of formula (H-2) and the red emitter of formula (G-3):

or
a blend of the arylamine matrix compound of formula (H-3) and the red emitter of formula (G-3):

17. The transistor of claim 1 , wherein each of the electron electrode, hole electrode, and gate electrode independently comprises a metal or a transparent conducting oxide, wherein optionally, such metal or transparent conducting oxide is selected from the group consisting of gold, silver, molybdenum, copper, titanium, chromium, tin-doped indium oxide and combination thereof, and wherein optionally, the electron electrode and the hole electrode are composed of different metals.

18. The transistor of claim 1 , wherein the dielectric layer comprises an electrically insulating material selected from the group consisting of an inorganic oxide or nitride, a molecular dielectric, a polymeric dielectr

Assignees

• Flexterra Inc
• E T C Srl

Inventors

• Facchetti Antonio
• Usta Hakan
• Denti Mitchell
• Biondo Viviana
• Soldano Caterina
• Muccini Michele

Classifications

• H01L51/0072

  Electricity · mapped topic

• H01L51/0061

  Electricity · mapped topic

• H01L51/0074

  Electricity · mapped topic

• H01L51/5296 Primary

  Electricity · mapped topic

• H01L51/5072

  Electricity · mapped topic