Electroactive materials
View Patent ↗A compound having at least two diarylamino moieties and at least 10% deuteration.
1. A compound having Formula I, Formula II, or 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;
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;
e is the same or different at each occurrence and is an integer from 1 to 6; and
n is an integer greater than 1
wherein the compound is at least 10% deuterated.
2. The compound of claim 1 , having at least one substituent group on an aryl ring, wherein deuteration is on the substituent group on an aryl ring.
3. The compound of claim 1 , wherein at least one of Ar 1 and Ar 2 is a deuterated aryl group.
4. The compound of claim 3 , wherein Ar 1 and Ar 2 are at least 20% deuterated.
5. The compound of claim 1 , having at least one substituent group on an aryl ring, wherein deuteration is present on both at least one substituent group and at least one aryl ring.
6. The compound of claim 1 , wherein deuteration is present on [T 1 -T 2 ].
7. The compound of claim 6 , wherein [T 1 -T 2 ] is at least 20% deuterated.
8. The compound of claim 7 , wherein Ar 1 and Ar 2 are at least 20% deuterated.
9. The compound of claim 6 , wherein at least one of Ar 1 and Ar 2 is a deuterated aryl group.
10. The compound of claim 1 , wherein [T 1 -T 2 ] is selected from the group consisting of:
and deuterated analogs thereof,
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.
11. The compound of claim 10 , wherein R is selected from the group consisting of C1-10 alkyl and C1-10 alkoxy.
12. The compound of claim 1 , wherein a is 1-3.
13. The compound of claim 12 , wherein M is selected from the group consisting of triarylamine units, an aromatic unit having a crosslinkable substituent, and deuterated analogs thereof.
14. 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 D, alkyl, alkoxy, siloxane and, silyl; or adjacent R 1 groups may be joined to form an aromatic ring;
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.
15. The compound of claim 1 , wherein Ar 2 is selected from the group consisting phenyl, p-biphenyl, p-terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, and deuterated analogs thereof.
16. The compound of claim 1 , wherein Ar 2 has a substituent comprising a crosslinking group.
17. The compound of claim 1 having Formula III, wherein c is at least 0.4.
18. The compound of claim 1 , wherein [T 1 -T 2 ] is a substituted biphenylene group, or deuterated analog thereof.
19. The compound of claim 1 , wherein [T 1 -T 2 ] is a binaphthylene group, or deuterated analog thereof.
20. 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 I, Formula II, or 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
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;
e is the same or different at each occurrence and is an integer from 1 to 6; and
n is an integer greater than 1
wherein the compound is at least 10% deuterated.
21. The device of claim 20 , wherein the active layer is a hole transport layer.
22. The device of claim 20 , wherein the hole transport layer consists essentially of the compound having Formula I, Formula II, or Formula III.
23. The device of claim 20 , wherein the active layer is an electroluminescent layer.
24. The device of claim 20 , wherein the active layer consists essentially of one or more electroluminescent materials and a compound having Formula I, Formula II, or Formula III.