Hole transport materials

Patent metadata

Field	Value
Publication number	US-9947872-B2
Application number	US-201515325936-A
Country	US
Kind code	B2
Filing date	Jul 2, 2015
Priority date	Jul 15, 2014
Publication date	Apr 17, 2018
Grant date	Apr 17, 2018

Abstract

There is disclosed a compound having Formula I

In Formula I: Ar 1 and Ar 3 are the same or different and are aryl groups; Ar 2 and Ar 4 are the same or different and are aryl groups; L is the same or different at each occurrence and can be H, D, halogen, aryl, arylamino, crosslinkable groups, deuterated aryl, deuterated arylamino, or deuterated crosslinkable groups; R 1 -R 4 are the same or different and can be H, D, alkyl, alkoxy, aryl, aryloxy, silyl, deuterated alkyl, deuterated alkoxy, deuterated aryl, deuterated aryloxy, or deuterated silyl; R 5 -R 8 are the same or different and can be D, F, alkyl, aryl, alkoxy, aryloxy, silyl, crosslinkable groups, deuterated alkyl, deuterated alkoxy, deuterated aryl, deuterated aryloxy, or deuterated silyl, where adjacent R 5 -R 8 groups can be joined together to form an aromatic ring; a and b are the same or different and are an integer from 0-3; c and d are the same or different at each occurrence and are an integer from 0-4; m and q are the same or different and are an integer from 1-6; and n is an integer greater than 0.

First claim

What is claimed is:

1. An organic electronic device comprising an anode, a cathode, and a photoactive layer therebetween, and further comprising a hole transport layer comprising a compound having Formula I

wherein:
Ar 1 and Ar 3 are the same or different and are aryl groups;
Ar 2 and Ar 4 are the same or different and are aryl groups;
L is the same or different at each occurrence and is selected from the group consisting of H, D, halogen, aryl, arylamino, crosslinkable groups, deuterated aryl, deuterated arylamino, and deuterated crosslinkable groups;
R 1 -R 4 are the same or different and are selected from the group consisting of H, D, alkyl, alkoxy, aryl, aryloxy, silyl, deuterated alkyl, deuterated alkoxy, deuterated aryl, deuterated aryloxy, and deuterated silyl;
R 5 -R 8 are the same or different and are selected from the group consisting of D, F, alkyl, aryl, alkoxy, aryloxy, silyl, crosslinkable groups, deuterated alkyl, deuterated alkoxy, deuterated aryl, deuterated aryloxy, and deuterated silyl, where adjacent R 5 -R 8 groups can be joined together to form an aromatic ring;
a and b are the same or different and are an integer from 0-3;
c and d are the same or different at each occurrence and are an integer from 0-4;
m and q are the same or different and are an integer from 1-6; and
n is an integer greater than 0.

2. The device of claim 1 , wherein Ar 1 -Ar 4 are aryl groups having no fused rings.

3. The device of claim 1 , wherein one or both of Ar 1 and Ar 3 has Formula a

where:
R 9 is the same or different at each occurrence and is selected from the group consisting of D, alkyl, alkoxy, siloxane and silyl;
p is the same or different at each occurrence and is an integer from 0-4;
r is an integer from 1 to 5; and
* indicates the point of attachment to L.

4. The device of claim 1 , wherein one or both of Ar 2 and Ar 4 has Formula d

where:
R 9 is the same or different at each occurrence and is selected from the group consisting of D, alkyl, alkoxy, siloxane and silyl;
p is the same or different at each occurrence and is an integer from 0-4;
q is an integer from 0-5; and
r is an integer from 1 to 5.

5. The device of claim 1 , wherein one or more of R 1 -R 4 are alkyl groups or deuterated alkyl groups having 1-5 carbons.

6. The device of claim 1 , wherein one or more of R 1 -R 4 are selected from the group consisting of phenyl, biphenyl, substituted derivatives thereof, and deuterated analogs thereof.

7. The device of claim 1 , wherein the compound has Formula I-b or Formula I-c

wherein:
Ar 1 and Ar 3 are the same or different and are aryl groups;
Ar 2 and Ar 4 are the same or different and are aryl groups;
L is the same or different at each occurrence and is selected from the group consisting of H, D, halogen, aryl, arylamino, crosslinkable groups, deuterated aryl, deuterated arylamino, and deuterated crosslinkable groups;
R 1 -R 4 are the same or different and are selected from the group consisting of H, D, alkyl, alkoxy, aryl, aryloxy, silyl, deuterated alkyl, deuterated alkoxy, deuterated aryl, deuterated aryloxy, and deuterated silyl;
R 5 -R 8 are the same or different and are selected from the group consisting of D, F, alkyl, aryl, alkoxy, aryloxy, silyl, crosslinkable groups, deuterated alkyl, deuterated alkoxy, deuterated aryl, deuterated aryloxy, and deuterated silyl, where adjacent R 5 -R 8 groups can be joined together to form an aromatic ring;
a and b are the same or different and are an integer from 0-3;
c and d are the same or different at each occurrence and are an integer from 0-4; and
n is an integer greater than 0.

8. The device of claim 1 , wherein n>10 and the compound is a polymer.

9. The device of claim 8 , wherein M n >20,000.

10. An organic electronic device comprising an anode, a cathode, and a photoactive layer therebetween, and further comprising a hole transport layer comprising a copolymer having at least one monomer unit of Formula I-m

wherein:
Ar 1 and Ar 3 are the same or different and are aryl groups;
Ar 2 and Ar 4 are the same or different and are aryl groups;
R 1 -R 4 are the same or different and are selected from the group consisting of H, D, alkyl, alkoxy, aryl, aryloxy, silyl, deuterated alkyl, deuterated alkoxy, deuterated aryl, deuterated aryloxy, and deuterated silyl;
R 5 -R 8 are the same or different and are selected from the group consisting of D, F, alkyl, aryl, alkoxy, aryloxy, silyl, crosslinkable groups, deuterated alkyl, deuterated alkoxy, deuterated aryl, deuterated aryloxy, and deuterated silyl, where adjacent R 5 -R 8 groups can be joined together to form an aromatic ring;
a and b are the same or different and are an integer from 0-3;
c and d are the same or different at each occurrence and are an integer from 0-4;
m and q are the same or different and are an integer from 1-6; and
* represents the point of attachment in the copolymer.

11. The device of claim 10 , wherein M n >20,000.

12. An organic electronic device comprising an anode, a cathode, and a photoactive layer therebetween, and further comprising a hole transport layer comprising a compound selected from the group consisting of Compound H2 through Compound H5 and Compound H7 through Compound H18:

where n is an integer greater than 0, and * indicates a point of attachment.

Assignees

• Du Pont

Inventors

• Fennimore Adam
• Radu Nora Sabina

Classifications

• C08G2261/314

  Condensed aromatic systems, e.g. perylene, anthracene or pyrene · CPC title

• C08G2261/3162

  Arylamines · CPC title

• C08G61/128

  Chemistry & Metallurgy · mapped topic

• H01L51/5056

  Electricity · mapped topic

• C08G2261/1412

  Saturated aliphatic units · CPC title