Electroactive materials
View Patent ↗There is provided a compound having Formula I or Formula II: In the Formula: Ar 1 is a single bond or an arylene; Ar 2 is an aryl group; Ar 3 is a single bond or an arylene; R 1 is selected from H, D, aryl groups, alkyl groups, silyl groups, siloxane groups, fluoroalkyl groups, alkoxy groups, and fluoroalkoxy groups, or the two R 1 groups may be joined together to form an aliphatic ring having 5-10 carbons; R 2 is selected from D, aryl groups, alkyl groups, silyl groups, siloxane groups, fluoroalkyl groups, alkoxy groups, or fluoroalkoxy groups; M is a conjugated moiety; a is an integer from 0 to 2; b is an integer from 0 to 3; n is an integer equal to or greater than 1; and x and y are mole fractions where x+y=1.0.
1. A polymer having a formula selected from the group consisting of Formula Ia, Formula Ic, and Formula Ie:
wherein:
Ar 1 is a single bond;
Ar 2 is the same or different at each occurrence and is an aryl group;
Ar 3 is the same or different at each occurrence and is an arylene;
R 1 is the same or different at each occurrence and is selected from the group consisting of H, D, aryl groups, alkyl groups, silyl groups, siloxane groups, fluoroalkyl groups, alkoxy groups, and fluoroalkoxy groups, or the two R 1 groups may be joined together to form an aliphatic ring having 5-10 carbons;
R 2 is the same or different at each occurrence and is selected from the group consisting of D, aryl groups, alkyl groups, silyl groups, siloxane groups, fluoroalkyl groups, alkoxy groups, and fluoroalkoxy groups;
n is an integer equal to or greater than 20;
b is the same or different at each occurrence and is an integer from 0 to 4;
c is the same or different at each occurrence and is an integer from 0 to 1;
d is the same or different at each occurrence and is an integer from 0 to 2; and
e is the same or different at each occurrence and is an integer from 0 to 3.
2. The compound of claim 1 , wherein Ar 2 is selected from the group consisting of naphthyl and a group having Formula IV
where:
R 3 is the same or different at each occurrence and is selected from the group consisting of 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 6.
3. The compound of claim 1 , wherein Ar 3 is selected from the group consisting of naphthylene, and a group having Formula III
R 3 is the same or different at each occurrence and is selected from the group consisting of alkyl, alkoxy, siloxane and silyl;
c is the same or different at each occurrence and is an integer from 0-4; and
m is an integer from 1 to 6.
4. A polymer having a formula selected from the group consisting of Formula Ia, Formula Ic, and Formula Ie:
wherein:
Ar 1 is a single bond;
Ar 2 is the same or different at each occurrence and is an aryl group;
Ar 3 is the same or different at each occurrence and is selected from the group consisting of a single bond and an arylene;
R 1 is the same or different at each occurrence and is selected from the group consisting of H, D, aryl groups, alkyl groups, silyl groups, siloxane groups, fluoroalkyl groups, alkoxy groups, and fluoroalkoxy groups, or the two R 1 groups may be joined together to form an aliphatic ring having 5-10 carbons;
R 2 is the same or different at each occurrence and is selected from the group consisting of D, aryl groups, alkyl groups, silyl groups, siloxane groups, fluoroalkyl groups, alkoxy groups, and fluoroalkoxy groups;
n is an integer equal to or greater than 20;
b is the same or different at each occurrence and is an integer from 0 to 4;
c is the same or different at each occurrence and is an integer from 0 to 1;
d is the same or different at each occurrence and is an integer from 0 to 2; and
e is the same or different at each occurrence and is an integer from 0 to 3,
wherein crosslinking substituents are present on at least one Ar 2 .
5. The compound of claim 1 , wherein R 1 is selected from an alkyl group having 1-12 carbon atoms and an alkoxy group having 1-12 carbon atoms.
6. The compound of claim 1 , wherein R 2 is selected from an alkyl group having 1-12 carbon atoms and an alkoxy group having 1-12 carbon atoms.
7. An organic electronic device comprising a first electrical contact layer, a second electrical contact layer and an active layer therebetween, wherein the active layer comprises a compound having a formula selected from the group consisting of Formula Ia, Formula Ic, and Formula Ie:
wherein:
Ar 1 is a single bond;
Ar 2 is the same or different at each occurrence and is an aryl group;
Ar 3 is the same or different at each occurrence and is an arylene;
R 1 is the same or different at each occurrence and is selected from the group consisting of H, D, aryl groups, alkyl groups, silyl groups, siloxane groups, fluoroalkyl groups, alkoxy groups, and fluoroalkoxy groups, or the two R 1 groups may be joined together to form an aliphatic ring having 5-10 carbons;
R 2 is the same or different at each occurrence and is selected from the group consisting of D, aryl groups, alkyl groups, silyl groups, siloxane groups, fluoroalkyl groups, alkoxy groups, and fluoroalkoxy groups;
n is an integer equal to or greater than 20;
b is the same or different at each occurrence and is an integer from 0 to 4;
c is the same or different at each occurrence and is an integer from 0 to 1;
d is the same or different at each occurrence and is an integer from 0 to 2; and
e is the same or different at each occurrence and is an integer from 0 to 3.
8. The device of claim 7 , wherein Ar 1 has Formula III
where:
R 3 is the same or different at each occurrence and is selected from the group consisting of alkyl, alkoxy, siloxane and silyl;
c is the same or different at each occurrence and is an integer from 0-4; and
m is an integer from 1 to 6.
9. The device of claim 7 , wherein Ar 2 is selected from the group consisting of naphthyl and a group having Formula IV
where:
R 3 is the same or different at each occurrence and is selected from the group consisting of 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 6.
10. The device of claim 7 , wherein Ar 3 is selected from the group consisting of naphthylene, and a group having Formula III
where:
R 3 is the same or different at each occurrence and is selected from the group consisting of alkyl, alkoxy, siloxane and silyl;
c is the same or different at each occurrence and is an integer from 0-4; and
m is an integer from 1 to 6.
11. An organic electronic device comprising a first electrical contact layer, a second electrical contact layer and an active layer therebetween, wherein the active layer comprises a compound having a formula selected from the group consisting of Formula Ia, Formula Ic, and Formula Ie:
wherein:
Ar 1 is a single bond;
Ar 2 is the same or different at each occurrence and is an aryl group;
Ar 3 is the same or different at each occurrence and is selected from the group consisting of a single bond and an arylene;
R 1 is the same or different at each occurrence and is selected from the group consisting of H, D, aryl groups, alkyl groups, silyl groups, siloxane groups, fluoroalkyl groups, alkoxy groups, and fluoroalkoxy groups, or the two R 1 groups may be joined together to form an aliphatic ring having 5-10 carbons;
R 2 is the same or different at each occurrence and is selected from the group consisting of D, aryl groups, alkyl groups, silyl groups, siloxane groups, fluoroalkyl groups, alkoxy groups, and fluoroalkoxy groups;
n is an integer equal to or greater than 20;
b is the same or different at each occurrence and is an integer from 0 to 4;
c is the same or different at each occurrence and is an integer from 0 to 1;
d is the same or different at each occurrence and is an integer from 0 to 2; and
e is the same or different at each occurrence and is an integer from 0 to 3,
wherein a crosslinking substituent is present on at least one Ar 2 .
12. The device of claim 7 , wherein the active layer is a hole transport layer and the layer consists essentially of a compound having a formula selected from the group consisting of Formula Ia, Formula Ic, and Formula Ie.
13. The device of claim 7 , wherein the active layer is a photoactive layer.
14. The polymer of claim 4 , wherein Ar 2 is selected from the group consisting of naphthyl and a group having Formula IV
where:
R 3 is the same or different at each occurrence and is selected from the group consisting of 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 6.
15. The polymer of claim 4 , wherein Ar 3 is selected from the group consisting of a single bond, naphthylene, and a group having Formula III
where:
R 3 is the same or different at each occurrence and is selected from the group consisting of alkyl, alkoxy, siloxane and silyl;
c is the same or different at each occurrence and is an integer from 0-4; and
m is an integer from 1 to 6.
16. The polymer of claim 4 , wherein R 1 is selected from an alkyl group having 1-12 carbon atoms and an alkoxy group having 1-12 carbon atoms.
17. The polymer of claim 4 , wherein R 2 is selected from an alkyl group having 1-12 carbon atoms and an alkoxy group having 1-12 carbon atoms.
18. The device of claim 11 , wherein Ar 1 has Formula III
where:
R 3 is the same or different at each occurrence and is selected from the group consisting of alkyl, alkoxy, siloxane and silyl;
c is the same or different at each occurrence and is an integer from 0-4; and
m is an integer from 1 to 6.
19. The device of claim 11 , wherein Ar 2 is selected from the group consisting of naphthyl and a group having Formula IV
where:
R 3 is the same or different at each occurrence and is selected from the group consisting of 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 6.
20. The device of claim 11 , wherein Ar 3 is selected from the group consisting of a single bond, naphthylene, and a group having Formula III
where:
R 3 is the same or different at each occurrence and is selected from the group consisting of alkyl, alkoxy, siloxane and silyl;
c is the same or different at each occurrence and is an integer from 0-4; and
m is an integer from 1 to 6.
21. The device of claim 11 , wherein the active layer is a hole transport layer and the layer consists essentially of a compound having a formula selected from the group consisting of Formula Ia, Formula Ic, and Formula Ie.
22. The device of claim 11 , wherein the active layer is a photoactive layer.