Electroactive materials

Patent metadata

Field	Value
Publication number	US-9685613-B2
Application number	US-201113990800-A
Country	US
Kind code	B2
Filing date	Dec 19, 2011
Priority date	Dec 20, 2010
Publication date	Jun 20, 2017
Grant date	Jun 20, 2017

Abstract

There is disclosed a compound having Formula I

In Formula I:
Ar 1 through Ar 4 are the same or different and are aryl groups; L is a spiro group, an adamantyl group, bicyclic cyclohexyl, deuterated analogs thereof, or substituted derivatives thereof; R 1 is the same or different at each occurrence and is D, F, alkyl, aryl, alkoxy, silyl, or a crosslinkable group, where adjacent R 1 groups can be joined together to form an aromatic ring; R 2 is the same or different at each occurrence and is H, D, or halogen; a is the same or different at each occurrence and is an integer from 0-4; and n is an integer greater than 0.

First claim

What is claimed is:

1. A compound having Formula I

wherein:
** indicates a point of attachment or R 2 ;
Ar 1 through Ar 4 are the same or different and are aryl groups;
R 1 is the same or different at each occurrence and is selected from the group consisting of D, F, alkyl, aryl, alkoxy, silyl, and a crosslinkable group, where adjacent R 1 groups can be joined together to form an aromatic ring;
R 2 is the same or different at each occurrence and is selected from the group consisting of H, D, and halogen;
a is the same or different at each occurrence and is an integer from 0-4;

wherein the compound is a small molecule, an oligomer or a polymer, and wherein

is selected from the group consisting of

where:
R is the same or different at each occurrence and is H or R 1 ; and
an asterisk indicates a point of attachment to a nitrogen of an arylamino group.

2. The compound of claim 1 , having Formula II

wherein:
** indicates a point of attachment or R 2 ;
Ar 1 and Ar 2 are the same or different and are aryl groups;
E is the same or different at each occurrence and is selected from the group consisting of a single bond, C(R 3 ) 2 , C(R 4 ) 2 C(R 4 ) 2 , O, Si(R 3 ) 2 , Ge(R 3 ) 2 ;
R 1 is the same or different at each occurrence and is selected from the group consisting of D, F, alkyl, aryl, alkoxy, silyl, and a crosslinkable group, where adjacent R 1 groups can be joined together to form an aromatic ring;
R 2 is the same or different at each occurrence and is selected from the group consisting of H, D, and halogen;
R 3 is the same or different at each occurrence and is selected from the group consisting of H, alkyl and aryl, where adjacent R 3 groups can be joined together to form an aliphatic ring;
R 4 is the same or different at each occurrence and is selected from the group consisting of H, D, and alkyl;
a is the same or different at each occurrence and is an integer from 0-4;

wherein the compound is a small molecule, an oligomer or a polymer, and wherein

is selected from the group consisting of

where:
R is the same or different at each occurrence and is H or R 1 ; and
an asterisk indicates a point of attachment to a nitrogen of an arylamino group.

3. The compound of claim 1 , having Formula III

wherein:
** indicates a point of attachment or R 2 ;
Ar 1 and Ar 2 are the same or different and are aryl groups;
R 1 is the same or different at each occurrence and is selected from the group consisting of D, F, alkyl, aryl, alkoxy, silyl, and a crosslinkable group, where adjacent R 1 groups can be joined together to form an aromatic ring;
R 2 is the same or different at each occurrence and is selected from the group consisting of H, D, and halogen;
R 5 is the same or different at each occurrence and is selected from the group consisting of D, F, alkyl, aryl, alkoxy, silyl, and a crosslinkable group;
R 6 through R 9 are the same or different at each occurrence and are selected from the group consisting of H, D, F, alkyl, aryl, alkoxy, silyl, and a crosslinkable group, with the proviso that at least one of R 6 and R 7 is alkyl or silyl, and at least one of R 8 and R 9 is alkyl or silyl;
a is the same or different at each occurrence and is an integer from 0-4;
b is the same or different at each occurrence and is an integer from 0-2;

wherein the compound is a small molecule, an oligomer or a polymer, and wherein

is selected from the group consisting of

where:
R is the same or different at each occurrence and is H or R 1 ; and
an asterisk indicates a point of attachment to a nitrogen of an arylamino group.

4. The compound of claim 1 , wherein Ar 1 and Ar 2 have Formula a

where:
R 10 is the same or different at each occurrence and is selected from the group consisting of D, alkyl, alkoxy, siloxane and silyl;
c is the same or different at each occurrence and is an integer from 0-4;
d is an integer from 0-5; and
m is an integer from 1 to 5.

5. The compound of claim 1 , wherein Ar 1 and Ar 2 are selected from the group consisting of phenyl, biphenyl, terphenyl, deuterated derivatives thereof, and derivatives thereof having one or more substituents selected from the group consisting of alkyl, alkoxy, silyl, and a substituent with a crosslinking group.

6. The compound of claim 1 , wherein a=0.

7. The compound of claim 2 , wherein R 3 is selected from the group consisting of phenyl, biphenyl, and fluoroalkyl.

8. The compound of claim 3 , wherein R 6 ═R 8 =alkyl.

9. The compound of claim 3 , wherein R 7 ═R 9 =alkyl.

10. An organic electronic device comprising a first electrical contact layer, a second electrical contact layer and an electroactive layer therebetween, wherein the electroactive layer comprises a compound according to claim 1 .

11. The device of claim 10 , wherein the electroactive layer is a hole transport layer.

12. The device of claim 10 , wherein the electroactive layer is an electroactive layer comprising a host compound having Formula I and a dopant.

13. The compound of claim 1 , wherein

14. The compound of claim 1 , wherein

is selected from the group consisting of

15. The compound of claim 1 , wherein

is selected from the group consisting of

16. A compound having Formula I

wherein:
Ar 1 through Ar 4 are the same or different and are aryl groups;
R 1 is the same or different at each occurrence and is selected from the group consisting of D, F, alkyl, aryl, alkoxy, silyl, and a crosslinkable group, where adjacent R 1 groups can be joined together to form an aromatic ring;
R 2 is the same or different at each occurrence and is selected from the group consisting of H, D, and halogen;
a is the same or different at each occurrence and is an integer from 0-4;
n=1; and

wherein

Assignees

• Radu Nora Sabina
• Fennimore Adam
• Du Pont

Inventors

• Radu Nora Sabina
• Fennimore Adam

Classifications

• C08G2261/95

  Use in organic luminescent diodes · CPC title

• C08G2261/5222

  electrofluorescent · CPC title

• C08G2261/512

  Hole transport · CPC title

• C08G2261/3424

  non-conjugated, e.g. paracyclophanes or xylenes · CPC title

• C08G2261/3162

  Arylamines · CPC title