IP Library Granted Patent US 9,574,084
Granted Patent B2
US 9,574,084 · App. 13/680,164 · Granted Feb 21, 2017

Hole transport composition

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Quick Facts
Patent No.
US 9,574,084
App. No.
13/680,164
Granted
Feb 21, 2017
Kind
B2
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.

Claims (54)

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.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2019
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: LG CHEM, LTD.
Reel/Frame 050150/0482 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 22, 2019
From: CHESTERFIELD, REID JOHN
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 048413/0424 →