Organic electronic devices prepared using decomposable polymer additives

Patent metadata

Field	Value
Publication number	US-9260443-B2
Application number	US-201113333547-A
Country	US
Kind code	B2
Filing date	Dec 21, 2011
Priority date	Jan 4, 2011
Publication date	Feb 16, 2016
Grant date	Feb 16, 2016

Abstract

A method of fabricating an organic device is provided comprising providing a first solution comprising an organic semiconductor or a precursor thereof; a solvent and a decomposable polymer additive, where the polymer additive is heated so that it decomposes into gas. The method is applicable to large scale fabrication of OLEDs, OPVs and OFET devices.

First claim

The invention claimed is:

1. A method of fabricating an organic device comprising
providing a first solution comprising an organic semiconductor compound or a precursor compound thereof, a solvent and a decomposable polymer additive, wherein the organic semiconductor compound or the precursor compound thereof, and the decomposable polymer additive are dissolved in the first solution;
casting said first solution; and
removing at least 80% of the polymer additive by decomposing the polymer additive into volatile small molecules.

2. The method of claim 1 , wherein the polymer additive is decomposed by radiation or heating the casted first solution to a temperature at or above the decomposition temperature of the polymer additive.

3. The method of claim 2 , wherein the decomposition temperature of the polymer additive is 400° C. or lower.

4. The method of claim 3 , wherein the polymer additive is either a linear or block copolymer.

5. The method of claim 4 , wherein the polymer additive is selected from the group consisting of polyethers, polyacrylates, polyisocyanurates, aliphatic polycarbonates, polyethylene carbonates, polyesters, polysulfones and polystyrene or poly (αmethyl styrene).

6. The method of claim 4 , wherein the polymer additive is selected from the group consisting of poly carbonate, poly-phenylene oxide, poly (methyl methacrylate), poly (4-vinyl phenol), poly (4-vinyl pyridine), polyaldehyde, and poly(lactide-co-glycolide).

7. The method of claim 1 , wherein the polymer additive of claim 1 produces a larger viscosity value of the first solution than that of the solution without the polymer by at least 0.2 cps.

8. The method of claim 6 , wherein the poly carbonate has the following structure:

where R is bivalent and R is an alkanediyl, alkenediyl or alkynediyl group with less than 10 carbon atoms.

9. The method of claim 1 , wherein said organic semiconductor compound or said precursor compound thereof is a compound with a molecular weight less than or equal to 2000.

10. The method of claim 4 , wherein said organic semiconductor compound or said precursor compound thereof is a porphyrin or a phthalocyanine.

11. The method of claim 1 , wherein the organic semiconductor compound is a polymer.

12. The method of claim 6 , wherein the polymer is selected from the group consisting of P3HT, MEH-PPV, PBTTT, PDBTTT and PCDTBT.

13. The method of claim 1 , wherein the organic semiconductor precursor compound is the following compound:

where Y1-Y4 are H or alkyl group; R1-R4 are H, alkyl group or aryl group, F, or Cl; Z1a-Z4b are H, or alkyl group; and M is bivalent metal.

14. The method of claim 1 , wherein the organic semiconductor precursor compound is 1,4:8,11:15,18:22,25-tetraethano-29H,31H-tetrabenzo[b,g,l,q]porphyrin.

15. The method of claim 1 , wherein the organic semiconductor compound is selected from the group consisting of a porphyrin, a phthalocyanine, and derivatives of C60, C70, C76, C80 and C84.

16. The method of claim 9 , wherein the PCBNB, PCBM, and SIMEF derivatives of C60, C70, C76, C80 and C84 are selected.

17. The method of claim 1 , wherein the device is coated with benzoporphyrin prior to casting said first solution.

18. The method of claim 1 , further comprising casting a second solution, wherein the second solution comprises a second compound selected from a group consisting of C60, C70, C76, C80, C84, and PCBNB, PCBM, and SIMEF derivatives of C60, C70, C76, C80 and C84.

19. The method of claim 1 , wherein the first solution can be effectively deposited on said device using inkjet printing and slot or blade coating.

20. An organic thin film transistor made according to the methods of claim 9 .

21. A photovoltaic device made according to the method of claim 12 .

22. A composition comprising
an organic semiconductor compound, or a precursor compound thereof, and a polymer additive, wherein at least 80% of the polymer additive is capable of decomposing into gas upon heating, wherein the organic semiconductor precursor is 1,4:8,11:15,18:22,25-tetraethano-29H,31H-tetrabenzo [b,g,l,q]porphyrin, or one of the following compounds with the following formula:

where Y1-Y4 are H or alkyl group; R1-R4 are H, alkyl group or aryl group, F, or Cl; Z1a-Z4b are H, or alkyl group; and M is bivalent metal.

23. A method of fabricating an organic device comprising
providing a first solution comprising:
an organic semiconductor compound or a precursor compound thereof,
a solvent and a decomposable polymer additive, wherein:
the organic semiconductor compound or the precursor compound thereof, and the decomposable polymer additive are dissolved in the first solution; and
the decomposable polymer additive is selected for an ability to increase the viscosity of the first solution;
casting said first solution; and
removing at least 80% of the polymer additive by decomposing the polymer additive into volatile small molecules.

24. A method of fabricating an organic device comprising:
providing a first solution comprising an organic semiconductor compound or a precursor compound thereof, a solvent and a decomposable polymer additive, wherein:
the organic semiconductor compound or the precursor compound thereof, and the decomposable polymer additive are dissolved in the first solution; and
the decomposable polymer additive comprises a poly carbonate;
casting said first solution; and
removing at least 80% of the polymer additive by decomposing the polymer additive into volatile small molecules.

Assignees

• Hawker Craig J
• Chabinyc Michael
• Ku Sung-Yu
• Liman Christopher
• Aramaki Shinji
• Wang Hengbin
• Niinomi Takaaki
• Univ California
• Mitsubishi Chem Corp

Inventors

• Hawker Craig J
• Chabinyc Michael
• Ku Sung-Yu
• Liman Christopher
• Aramaki Shinji
• Wang Hengbin
• Niinomi Takaaki

Classifications

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• H01L51/0558

  Electricity · mapped topic

• H01L51/0037

  Electricity · mapped topic

• C07D487/22 Primary

  in which the condensed system contains four or more hetero rings · CPC title