Method and composition

Patent metadata

Field	Value
Publication number	US-10756272-B2
Application number	US-201716314310-A
Country	US
Kind code	B2
Filing date	Jun 27, 2017
Priority date	Jun 28, 2016
Publication date	Aug 25, 2020
Grant date	Aug 25, 2020

Abstract

A method of forming an n-doped organic semiconductor, the method comprising: formation of an n-dopant reagent by reaction of a composition comprising two or more precursor units for forming the n-dopant reagent and an organic semiconductor; and n-doping the organic semiconductor. One or more of the precursor units may be a substituent of a polymeric repeat unit. The n-doped organic semiconductor may be an electron-injection layer of an organic light-emitting device.

First claim

The invention claimed is:

1. A method of forming an n-doped organic semiconductor, the method comprising:
formation of an n-dopant reagent by reaction of a composition comprising two or more precursor units for forming the n-dopant reagent and an organic semiconductor; and
n-doping the organic semiconductor, wherein the composition comprises a first precursor polymer comprising a repeat unit of formula (I):

wherein BG1 is a first backbone group; Sp 1 is a first spacer group; P-1 is a first precursor unit; R 6 is a substituent; t1 is 0 or a positive integer; u1 is 0 or 1; v1 is 1 if u1 is 0; v1 is at least 1 if u1 is 1; and w1 is at least 1.

2. The method according to claim 1 , wherein P-1 is a group of formula (VII):

wherein R 1 independently in each occurrence is a substituent; R 2 independently in each occurrence is H or a substituent; and x is 0, 1, 2, 3 or 4, with the proviso that one of R 1 and R 2 is a direct bond to BG1 or, if present, to Sp 1 .

3. The method according to claim 1 , wherein the first precursor polymer is a conjugated polymer.

4. The method according to claim 3 , wherein BG1 is a C 6-20 arylene group.

5. The method according to claim 1 , wherein the composition comprises a second precursor polymer comprising a repeat unit of formula (II):

wherein BG2 is a second backbone group; Sp 2 is a second spacer group; P-2 is a second precursor unit; R 6 is a substituent; t2 is 0 or a positive integer; u2 is 0 or 1; v2 is 1 if u2 is 0; v2 is at least 1 if u2 is 1; and w2 is at least 1.

6. The method according to claim 5 , wherein P-2 is a group of formula (VIII):

wherein R 3 and R 4 are each independently H or a substituent; R 5 independently in each occurrence is a substituent; and y is 0, 1, 2, 3 or 4, with the proviso that one of R 3 , R 4 and R 5 is a direct bond to BG2 or, if present, to Sp 2 .

7. The method according to claim 5 , wherein the second precursor polymer is a conjugated polymer.

8. The method according to claim 1 , wherein the organic semiconductor is a polymer.

9. The method according to claim 8 , wherein at least one precursor unit is a substituent of the organic semiconductor polymer.

10. The method according to claim 1 , wherein the composition is in the solid state at 20° C.

11. The method according to claim 1 , wherein the composition is heated to form the n-dopant reagent.

12. The method according to claim 11 , wherein the composition is heated to above the glass transition temperature of a polymer of the composition.

13. A method of forming an organic electronic device wherein an n-doped organic semiconductor layer of the device is formed by forming a precursor layer comprising the precursor units and the organic semiconductor according to claim 1 ; reacting the precursor units to form the n-dopant reagent; and n-doping the organic semiconductor.

14. The method according to claim 13 , wherein the organic electronic device is an organic light-emitting device comprising an anode, a cathode, a light-emitting layer between the anode and the cathode and an electron-injection layer between the light-emitting layer and the cathode wherein the electron-injection layer is the n-doped organic semiconducting layer.

15. A composition comprising two or more precursor units for forming an n-dopant reagent and an organic semiconductor wherein the two or more precursor units and the organic semiconductor are as defined in claim 1 .

16. A formulation comprising the composition according to claim 15 dissolved in a solvent.

17. A method of forming an n-doped organic semiconductor, the method comprising:
formation of an n-dopant reagent by reaction of a first precursor unit and a second precursor unit of a precursor polymer in a composition comprising the precursor polymer and an organic semiconductor; and
n-doping the organic semiconductor, wherein the precursor polymer comprises a repeat unit of formula (I) and a repeat unit of formula (II):

wherein BG1 is a first backbone group; Sp 1 is a first spacer group; P-1 is a first precursor unit; R 6 is a substituent; t1 is 0 or a positive integer; u1 is 0 or 1; v1 is 1 if u1 is 0; v1 is at least 1 if u1 is 1; w1 is at least 1; BG2 is a second backbone group; Sp 2 is a second spacer group; P-2 is a second precursor unit; R 6 is a substituent; t2 is 0 or a positive integer; u2 is 0 or 1; v2 is 1 if u2 is 0; v2 is at least 1 if u2 is 1; and w2 is at least 1.

18. A method of forming an n-doped organic semiconductor, the method comprising:
formation of an n-dopant reagent by reaction of a first precursor unit and a second precursor unit of a precursor polymer in a composition comprising the precursor polymer and an organic semiconductor; and
n-doping the organic semiconductor, wherein the precursor polymer comprises a repeat unit of formula (VI):

wherein BG3 is a backbone group; P-1 is a first precursor unit; P-2 is a second precursor unit; Sp 3 in each occurrence is independently a spacer group; R 6 is a substituent; t3 is 0 or a positive integer; u31 is 0 or 1; u32 is 0 or 1; v31 is 1 if u31 is 0; v31 is at least 1 if u31 is 1; v32 is 1 if u32 is 0; v32 is at least 1 if u32 is 1; and w3 independently in each occurrence is at least 1.

Assignees

• Sumitomo Chemical Co
• Sumitmoor Chemical Company Ltd

Inventors

• Kugler Thomas
• Bourcet Florence
• Zuberi Sheena

Classifications

• C09K19/58

  Dopants or charge transfer agents · CPC title

• H10K71/30 Primary

  Doping active layers, e.g. electron transporting layers · CPC title

• H10K50/165

  comprising dopants · CPC title

• H10K85/151

  Copolymers · CPC title

• H10K85/115

  Polyfluorene; Derivatives thereof · CPC title