Hole transport composition

Patent metadata

Field	Value
Publication number	US-9574084-B2
Application number	US-201213680164-A
Country	US
Kind code	B2
Filing date	Nov 19, 2012
Priority date	May 16, 2008
Publication date	Feb 21, 2017
Grant date	Feb 21, 2017

Abstract

There is provided a hole transport composition having (i) a first hole transport polymer having crosslinkable groups, and (ii) a second hole transport polymer having substantially no crosslinkable groups. There is also provided a crosslinked hole transport layer and an electronic device containing the crosslinked hole transport layer.

First claim

What is claimed is:

1. A hole transport composition comprising (i) a first hole transport polymer having crosslinkable groups, and (ii) a second hole transport polymer having substantially no crosslinkable groups, wherein said first hole transport polymer is a copolymer of a triarylamine derivative and a fluorene derivative and wherein said second hole transport polymer is a triarylamine polymer.

2. The hole transport composition of claim 1 , wherein the first hole transport polymer has a narrower band gap than the second hole transport polymer.

3. The hole transport composition of claim 1 , wherein the first polymer comprises a monomer having Formula I:

where:
R and Y are independently selected from the group consisting of H, D, alkyl, fluoroalkyl, aryl, fluoroaryl, alkoxy, aryloxy, NR″ 2 , R′,

R′ is a crosslinkable group;
R″ is independently selected from the group consisting of H, alkyl, fluoroalkyl, aryl, fluoroaryl, and R′;
X can be the same or different at each occurrence and is a leaving group;
Z is C, Si, or N;
Q is (ZR″ n ) b ;
a is an integer from 0 to 5;
b is an integer from 0 to 20;
c is an integer from 0 to 4;
q is an integer from 0 to 7; and
n is an integer from 1 to 2;
with the proviso that there is at least one crosslinking group.

4. The hole transport composition of claim 3 , wherein the hole transport polymer is a copolymer made from a monomer having Formula I and at least one comonomer selected from the group consisting of Formulae II through VII:

where R is independently selected from the group consisting of aryl, fluoroaryl, and aryloxy;
X can be the same or different at each occurrence and is a leaving group;
c is an integer from 0 to 4;
with the proviso that there is at least one crosslinking group.

5. The hole transport composition of claim 3 , wherein the first hole transport polymer has a narrower band gap than the second hole transport polymer.

6. The hole transport composition of claim 1 , wherein the second hole transport polymer has Formula IX or Formula X:

wherein:
Ar 1 is the same or different at each occurrence and is selected from the group consisting of phenylene and naphthylene;
Ar 2 is the same or different at each occurrence and is an aryl group;
M is the same or different at each occurrence and is a conjugated moiety;
T 1 and T 2 are independently the same or different at each occurrence and are conjugated moieties which are connected in a non-planar configuration;
d is an integer from 1 to 6;
e, f, and g are mole fractions such that e+f+g=1.0, with the proviso that f is not zero, and at least one of e and g is not zero, and when e is zero, M comprises at least two triarylamine units; and
m is an integer greater than 5.

7. The composition of claim 1 , wherein the crosslinkable groups are selected from the group consisting of vinyl, acrylate, perfluorovinylether, 1-benzo-3,4-cyclobutane, siloxane, cyanate groups, cyclic ethers (epoxides), cycloalkenes, and acetylenic groups.

8. A hole transport composition comprising (i) a first hole transport polymer having crosslinkable groups, and (ii) a second hole transport polymer having substantially no crosslinkable groups, wherein the first hole transport polymer is a polymer made from a monomer having Formula I:

where:
R and Y are independently selected from the group consisting of H, D, alkyl, fluoroalkyl, aryl, fluoroaryl, alkoxy, aryloxy, NR″ 2 , R′,

R′ is a crosslinkable group;
R″ is independently selected from the group consisting of H, alkyl, fluoroalkyl, aryl, fluoroaryl, and R′;
X can be the same or different at each occurrence and is a leaving group;
Z is C, Si, or N;
Q is (ZR″ n ) b ;
a is an integer from 0 to 5;
b is an integer from 0 to 20;
c is an integer from 0 to 4;
q is an integer from 0 to 7; and
n is an integer from 1 to 2;
with the proviso that the first hole transport polymer has at least one crosslinking group, and wherein the second hole transport polymer has Formula IX or Formula X:

wherein:
Ar 1 is the same or different at each occurrence and is selected from the group consisting of phenylene and naphthylene;
Ar 2 is the same or different at each occurrence and is an aryl group;
M is the same or different at each occurrence and is a conjugated moiety;
T 1 and T 2 are independently the same or different at each occurrence and are conjugated moieties which are connected in a non-planar configuration;
d is an integer from 1 to 6;
e, f, and g are mole fractions such that e+f+g=1.0, with the proviso that f is not zero, and at least one of e and g is not zero, and when e is zero, M comprises at least two triarylamine units; and
m is an integer greater than 5.

Assignees

• Du Pont

Inventors

• Chesterfield Reid John

Classifications

• H01B1/121

  Charge-transfer complexes · CPC title

• C08G2261/95

  Use in organic luminescent diodes · CPC title

• C08G2261/512

  Hole transport · CPC title

• C08G61/12

  Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule · CPC title

• C08L79/02 Primary

  Polyamines · CPC title