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 O, S, SO, SO 2 , Se, Te, NR, BR, PR, PO, PO 2 , and SiR 2 ;
R is the same or different at each occurrence and is independently selected from the group consisting of hydrogen, alkyl, aryl, alkenyl, and alkynyl;
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.
2. The electroactive material of claim 1 , wherein Q is selected from the group consisting of O and S.
3. The electroactive material of claim 1 , wherein at least one of R 2 and R 4 is selected from the group consisting of alkyl, aryl, and diarylamino.
4. The electroactive material of claim 1 , wherein at least one of R 1 and R 3 are selected from the group consisting of alkyl, aryl, and diarylamino.
5. 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.
6. The electroactive material of claim 1 , selected from the group consisting of Compound 1 through Compound 4:
7. An electroactive polymer having at least one monomeric unit selected from the group consisting of Formula II, Formula III, and combinations thereof:
wherein:
Q is the same or different at each occurrence and is independently selected from the group consisting of O, S, SO, SO 2 , Se, Te, NR, BR, PR, PO, PO 2 , and SiR 2 ;
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
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.
8. The polymer of claim 7 , wherein the polymer is a homopolymer.
9. The polymer of claim 7 , 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 O, S, SO, SO 2 , Se, Te, NR, BR, PR, PO, PO 2 , and SiR 2 ;
R is the same or different at each occurrence and is independently selected from the group consisting of hydrogen, alkyl, aryl, alkenyl, and alkynyl;
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
a and b represent mole fractions, such that a+b=1.
10. The polymer of claim 9 , wherein Ar is selected from the group consisting of Ar1 through Ar92
Ar1
Ar2
Ar3
Ar4
Ar5
Ar6
Ar7
Ar8
Ar9
Ar10
Ar11
Ar12
Ar13
Ar14
Ar15
Ar16
Ar17
Ar18
Ar19
Ar20
Ar21
Ar22
Ar23
Ar24
Ar25
Ar26
Ar27
Ar28
Ar29
Ar30
Ar31
Ar32
Ar33
Ar34
Ar35
Ar36
Ar37
Ar38
Ar39
Ar40
Ar41
Ar42
Ar43
Ar44
Ar45
Ar46
Ar47
Ar48
Ar49
Ar50
Ar51
Ar52
Ar53
Ar54
Ar55
Ar56
Ar57
Ar58
Ar59
Ar60
Ar61
Ar62
Ar63
Ar64
Ar65
Ar66
Ar67
Ar68
Ar69
Ar70
Ar71
Ar72
Ar73
Ar74
Ar75
Ar76
Ar77
Ar78
Ar79
Ar80
Ar81
Ar82
Ar83
Ar84
Ar85
Ar86
Ar87
Ar88
Ar89
Ar90
Ar91
Ar92
11. The polymer of claim 9 , wherein Ar is selected from the group consisting of phenylene, naphthylene, biphenylene, binaphthylene, anthracenylene, fluorenylene, diarylamine and combinations thereof.
12. The polymer of claim 9 selected from the group consisting of Compound 5 through Compound 7:
13. 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 and a polymer having at least one monomeric unit selected from the group consisting of Formula II, Formula III, and combinations thereof
wherein:
Q is the same or different at each occurrence and is independently selected from the group consisting of O, S, SO, SO 2 , Se, Te, NR, BR, PR, PO, PO 2 , and SiR 2 ;
R is the same or different at each occurrence and is independently selected from the group consisting of hydrogen, alkyl, aryl, alkenyl, and alkynyl;
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.
14. The device of claim 13 , 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 O, S, SO, SO 2 , Se, Te, NR, BR, PR, PO, PO 2 , and SiR 2 ;
R is the same or different at each occurrence and is independently selected from the group consisting of hydrogen, alkyl, aryl, alkenyl, and alkynyl;
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
a and b represent mole fractions, such that a+b=1.
15. The device of claim 14 , wherein Ar is selected from the group consisting of Ar1 through Ar92
Ar1
Ar2
Ar3
Ar4
Ar5
Ar6
Ar7
Ar8
Ar9
Ar10
Ar11
Ar12
Ar13
Ar14
Ar15
Ar16
Ar17
Ar18
Ar19
Ar20
Ar21
Ar22
Ar23
Ar24
Ar25
Ar26
Ar27
Ar28
Ar29
Ar30
Ar31
Ar32
Ar33
Ar34
Ar35
Ar36
Ar37
Ar38
Ar39
Ar40
Ar41
Ar42
Ar43
Ar44
Ar45
Ar46
Ar47
Ar48
Ar49
Ar50
Ar51
Ar52
Ar53
Ar54
Ar55
Ar56
Ar57
Ar58
Ar59
Ar60
Ar61
Ar62
Ar63
Ar64
Ar65
Ar66
Ar67
Ar68
Ar69
Ar70
Ar71
Ar72
Ar73
Ar74
Ar75
Ar76
Ar77
Ar78
Ar79
Ar80
Ar81
Ar82
Ar83
Ar84
Ar85
Ar86
Ar87
Ar88
Ar89
Ar90
Ar91
Ar92
16. The device of claim 14 , wherein Ar is selected from the group consisting of phenylene, naphthylene, biphenylene, binaphthylene, anthracenylene, fluorenylene, diarylamine and combinations thereof.
17. The device of claim 13 , wherein the electroactive layer is a charge transport layer.
18. The device of claim 17 , wherein the charge transport layer is a hole transport layer.
19. The device of claim 13 , wherein the electroactive layer is a photoactive layer.
20. The device of claim 19 , wherein the photoactive layer further comprises a host material.
21. The device of claim 19 , wherein the photoactive layer further comprises a photoactive material.
22. The polymer of claim 7 having at least 5 repeating units.
23. The polymer of claim 9 , wherein a is 0.3 to 0.7 and b is 0.3 to 0.7.