Electroactive materials
View Patent ↗A compound having Formula I, Formula II, or Formula III: Ar 1 may independently be phenylene, substituted phenylene, naphthylene, or substituted 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; a and e are the same or different at each occurrence and are an integer from 1 to 6; b, c, and d are mole fractions such that b+c+d=1.0, with the proviso that c is not zero, and at least one of b and d is not zero, and when b is zero, M has at least two triarylamine units; and n is an integer greater than 1.
1. A compound having Formula III:
wherein:
Ar 1 is the same or different at each occurrence and is selected from the group consisting of phenylene, substituted phenylene, naphthylene, and substituted 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;
a is the same or different at each occurrence and is an integer from 1 to 6;
b, c, and d are mole fractions such that b+c+d=1.0, with the proviso that c is not zero, and at least one of b and d is not zero, and when b is zero, M comprises at least two triarylamine units; and
e is the same or different at each occurrence and is an integer from 1 to 6;
wherein the members of [T1-T2] are independently selected from the group consisting of:
where:
R is the same or different and is selected from the group consisting of alkyl, aryl, alkoxy, aryloxy, fluoroalkyl, fluoroaryl, fluoroaryloxy fluoroalkyloxy, oxyalkyl, and alkenyl groups.
2. The compound of claim 1 , wherein R is selected from the group consisting of C1-10 alkyl and C1-10 alkoxy; wherein the members of [T1-T2] are independently selected from the group consisting of:
3. The compound of claim 1 , wherein R is selected from the group consisting of C3-8 branched alkyl and C3-8 branched alkoxy; wherein the members of are independently selected from the group consisting of:
4. The compound of claim 1 , wherein both R groups are joined together to form a non-aromatic ring; wherein the members of [T1- T2] are independently selected from the group consisting of:
5. The compound of claim 1 , wherein a is 1-3; wherein b is not equal to 0.
6. The compound of claim 1 , wherein Ar 2 has Formula a
where:
R 1 is the same or different at each occurrence and is selected from the group consisting of alkyl, alkoxy, and silyl;
f is the same or different at each occurrence and is an integer from 0-4;
g is an integer from 0-5; and
m is an integer from 1 to 5;wherein b is not equal to 0.
7. The compound of claim 1 , wherein Ar 2 is selected from the group consisting phenyl, p-biphenyl, p-terphenyl, naphthyl, phenylnaphthyl, and naphthylphenyl ;wherein b is not equal to 0.
8. The compound of claim 1 , wherein Ar 2 has a substituent comprising a crosslinking group; wherein b is not equal to 0.
9. The compound of claim 1 , wherein at least one Ar 2 has at least one substituent selected from the group consisting of alkyl, alkoxy and silyl wherein b is not equal to 0.
10. The compound of claim 1 having Formula III, wherein c is at least 0.4.
11. The compound of claim 10 , wherein M is selected from the group consisting of triarylamine units and an aromatic unit having a crosslinkable substituent; wherein b is not equal to 0.
12. A compound selected from the group consisting of
13. 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 Formula III:
wherein:
Ar 1 is the same or different at each occurrence and is selected from the group consisting of phenylene, substituted phenylene, naphthylene, and substituted 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;
a is the same or different at each occurrence and is an integer from 1 to 6;
b, c, and d are mole fractions such that b+c+d=1.0, with the proviso that c is not zero, and at least one of b and d is not zero, and when b is zero, M comprises at least two triarylamine units; and
e is the same or different at each occurrence and is an integer from 1 to 6;
wherein the members of [T 1 -T 2 ] are independently selected from the group consisting of:
where:
R is the same or different and is selected from the group consisting of alkyl, aryl, alkoxy, aryloxy, fluoroalkyl, fluoroaryl, fluoroaryloxy fluoroalkyloxy, oxyalkyl, and alkenyl groups.
14. The device of claim 13 , wherein the active layer is a hole transport layer.
15. The device of claim 14 , wherein the hole transport layer consists essentially of the Compound having Formula III.
16. The device of claim 13 , wherein the active layer is a photoactive layer.
17. The device of claim 16 , wherein the active layer further comprises a photoactive material.
18. The device of claim 17 , wherein the active layer consists essentially of a photoactive material and a compound Formula III.
19. The compound of claim 1 , wherein at least one Ar 1 is a substituted phenyl with a substituent selected from the group consisting of alkyl, alkoxy, silyl, and a substitutent with a crosslinking group; wherein b is not equal to 0.
20. A compound having Formula III:
wherein:
Ar 1 is the same or different at each occurrence and is selected from the group consisting of phenylene, substituted phenylene, naphthylene, and substituted 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;
a is the same or different at each occurrence and is an integer from 1 to 6;
b, c, and d are mole fractions such that b+c+d=1.0, with the proviso that c is not zero, M comprises at least two triarylamine units; and e is the same or different at each occurrence and is an integer from 1 to 6; wherein b is not zero; wherein the members of [T1-T2] are independently selected from the group consisting of:
21. 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 Formula III:
wherein:
Ar 1 is the same or different at each occurrence and is selected from the group consisting of phenylene, substituted phenylene, naphthylene, and substituted 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;
a is the same or different at each occurrence and is an integer from 1 to 6;
b, c, and d are mole fractions such that b+c+d=1.0, with the proviso that c is not zero, M comprises at least two triarylamine units; and
e is the same or different at each occurrence and is an integer from 1 to 6;
wherein b is not zero; wherein the members of [T1-T2] are independently selected from the group consisting of: