Electroactive materials
View Patent ↗There is provided an electroactive material having Formula I wherein: Q is the same or different at each occurrence and can be O, S, Se, Te, NR, SO, SO 2 , or SiR 3 ; R is the same or different at each occurrence and can be hydrogen, alkyl, aryl, alkenyl, or alkynyl; R 1 through R 8 are the same or different and can be hydrogen, alkyl, aryl, halogen, hydroxyl, aryloxy, alkoxy, alkenyl, alkynyl, amino, alkylthio, phosphino, silyl, —COR, —COOR, —PO 3 R 2 , —OPO 3 R 2 , or CN.
1. An electroactive material having Formula I:
wherein:
Q is the same or different at each occurrence and is independently selected from the group consisting of S, SO, SO 2 , Se, and Te;
R 1 through R 8 are the same or different and are independently selected from the group consisting of hydrogen, alkyl, aryl, halogen, hydroxyl, aryloxy, alkoxy, alkenyl, alkynyl, amino, alkylthio, phosphino, silyl, —COR, —COOR, —PO 3 R 2 , —OPO 3 R 2 , and CN and at least one of R 1 through R 8 is diarylamino R is the same or different at each occurrence and is indpendently selected from the group consisting of hydrogen, alkyl, aryl, alkenyl, and alkynyl.
2. The electroactive material of claim 1 , wherein Q is S.
3. The electroactive material of claim 1 , wherein at least one of R 5 , R 6 , R 7 , and R 8 is selected from the group consisting of alkyl, aryl, and diarylamino.
4. The electroactive material of claim 1 , selected from the group consisting of Compound 28 and 29;
5. An electroactive polymer having at least one monomeric unit selected from the group consisting of Formula II and Formula III, or an electroactive polymer having at least two monomeric units wherein the first unit is of Formula II and a second unit is of Formula III:
wherein:
Q is the same or different at each occurrence and is independently selected from the group consisting of S, SO, and SO 2 ;
and
R 1 through R 8 are the same or different and are independently selected from the group consisting of hydrogen, alkyl, aryl, halogen, hydroxyl, aryloxy, alkoxy, alkenyl, alkynyl, amino, alkylthio, phosphino, silyl, —COR, —COOR, —PO 3 R 2 , —OPO 3 R 2 , and CN and at least one of R 1 through R 8 is diarylamino R is the same or different at each occurrence and is independently selected from the group consisting of hydrogen, alkyl, aryl, alkenyl, and alkynyl.
6. The polymer of claim 5 , wherein the polymer is a homopolymer.
7. The polymer of claim 5 , having Formula IV or V:
wherein:
Ar is the same or different at each occurrence and is an aromatic unit;
Q is the same or different at each occurrence and is independently selected from the group consisting of S, SO, SO 2 , Se, and Te;
R 1 through R 8 are the same or different and are independently selected from the group consisting of hydrogen, alkyl, aryl, halogen, hydroxyl, aryloxy, alkoxy, alkenyl, alkynyl, amino, alkylthio, phosphino, silyl, —COR, —COOR, —PO 3 R 2 , —OPO 3 R 2 , and CN and at least one of R 1 through R 8 is diarylamino; R is the same or different at each occurrence and is independently selected from the group consisting of hydrogen, alkyl, aryl, alkenyl, and alkynyl; and
a and b represent mole fractions, such that a+b=1.
8. The polymer of claim 7 , wherein Ar is selected from the group consisting of phenylene, naphthylene, biphenylene, binaphthylene, anthracenylene, fluorenylene, diarylamine and combinations thereof.
9. An organic electronic device comprising a first electrical contact, a second electrical contact and an electroactive layer therebetween, the electroactive layer comprising an electroactive material selected from the group consisting of a compound having Formula I, a polymer having at least one monomeric unit of Formula II, a polymer having at least one monomeric unit of Formula III, and a polymer having at least two monomeric units wherein the first unit if of Formula II and a second unit is of Formula III
wherein:
Q is the same or different at each occurrence and is independently selected from the group consisting of S, SO, SO 2 , Se, and Te;
R 1 through R 6 are the same or different and are independently selected from the group consisting of hydrogen, alkyl, aryl, halogen, hydroxyl, aryloxy, alkoxy, alkenyl, alkynyl, amino, alkylthio, phosphino, silyl, —COR, —COOR, —PO 3 R 2 , —OPO 3 R 2 , and CN and at least one of R 1 through R 8 is diarylamino; R is the same or different at each occurrence and is independently selected from the group consisting of hydrogen, alkyl, aryl, alkenyl, and alkynyl; and
a and b represent mole fractions, such that a+b=1.
10. The device of claim 9 , wherein the polymer has Formula IV or V:
wherein:
Ar is the same or different at each occurrence and is an aromatic unit;
Q is the same or different at each occurrence and is independently selected from the group consisting of S, SO, SO 2 , Se, and Te;
R 1 through R 8 are the same or different and are independently selected from the group consisting of hydrogen, alkyl, aryl, halogen, hydroxyl, aryloxy, alkoxy, alkenyl, alkynyl, amino, alkylthio, phosphino, silyl, —COR, —COOR, —PO 3 R 2 , —OPO 3 R 2 , and CN and at least one of R 1 through R 8 is diarylamino; R is the same or different at each occurrence and is independently selected from the group consisting of hydrogen, alkyl, aryl, alkenyl, and alkynyl; and
a and b represent mole fractions, such that a+b=1.
11. The device of claim 9 , wherein the electroactive layer is a charge transport layer.
12. The device of claim 11 , wherein the charge transport layer is a hole transport layer.
13. The device of claim 9 , wherein the electroactive layer is a photoactive layer.
14. The device of claim 13 , where the photoactive layer further comprises a host material.
15. The device of claim 13 , wherein the photoactive layer further comprises a photoactive material.