Functional materials based on stable chemical structure

1. A compound of General Formula I:

wherein:

T 2 and T 3 represent a Donor or an Acceptor; T 1 optionally represents a Donor;

Y 1 and Y 2 each independently represent C, N, Si, B, or P;

wherein when Y 1 and Y 2 both represent C, then two groups R 1 may optionally together form a fused aryl or heteroaryl ring having the following structure:

wherein for any two adjacent X a and X b representing X 5 -X 8 where a and b are integers from 5-8, then two groups R 2 may optionally together form a fused aryl or heteroaryl ring having the following structure:

wherein for any two adjacent X c and X d representing X 9 -X 12 where c and d are integers from 9-12, then two groups R 3 may optionally together form a fused aryl or heteroaryl ring having the following structure:

wherein:

X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , and X 16 each independently represents C, N, Si, B, or P;

U 1 represents O, S, Se, NR 21 , P═O, As═O, Bi═O, CR 21 R 22 , C═O, SiR 21 R 22 , GeR 21 R 22 , NR 21 , PR 21 , PR 21 R 22 , R 21 P═O, AsR 21 , R 21 As═O, S═O, SeO 2 , Se═O, SeO 2 , BR 21 , BR 21 R 22 , AlR 21 , AlR 21 R 22 , R 21 Bi═O, or BiR 21 ;

each n is independently an integer, valency permitting; and

each of R 1 , R 2 , R 3 , R 4 , R 5 , R 21 and R 22 independently represents hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof;

wherein two adjacent groups R 1 , R 2 , R 3 , R 4 , R 5 , R 21 , R 22 , or a combination thereof may optionally together form a fused ring; and

wherein at least one of the following conditions (i)-(iii) is satisfied:

(i) two groups R 1 together form a fused heteroaryl structure having the structure

 or

(ii) X 9 and X 10 each represent C substituted by R 3 , wherein the two groups R 3 are represented by the following structure:

wherein the dashed lines indicate bonds to X 9 and X 10 , and

X 11 and X 12 each represent C substituted by R 3 , wherein the two groups R 3 are represented by the following structure:

wherein the dashed lines indicate bonds to X 11 and X 12 , or

(iii) at least one of Y 1 and Y 2 represents C, and at least one R 1 is represented by the following structure:

2. The compound of claim 1 , wherein one or more of the following conditions is true:

(i) Y 1 and Y 2 are each C, and two groups R 1 are represented by one of the following structures, where dashed lines indicate bonds to Y 1 and Y 2 in General Formula I:

(ii) for two adjacent X a and X b , two groups R 2 are represented by one of the following structures, where dashed lines indicate bonds to X a and X b in General Formula I:

(iii) for two adjacent X c and X 4 , two groups R 3 are represented by one of the following structures, where dashed lines indicate bonds to X 9 and X d in General Formula I:

wherein:

X 13 , X 14 , X 15 , X 16 , X 17 , X 18 , X 19 , and X 20 each independently represents C, N, Si, B, or P;

each U 1 and U 2 represents O, S, Se, P═O, As═O, Bi═O, CR 21 R 22 , C═O, SiR 21 R 22 , GeR 21 R 22 , NR 21 , PR 21 , PR 21 R 22 , R 21 P═O, AsR 21 , R 21 As═O, S═O, SeO 2 , Se═O, SeO 2 , BR 21 , BR 21 R 22 , AlR 21 , AlR 21 R 22 , R 21 Bi═O, or BiR 21 ;

each R 4 , R 5 , R 6 , and R 7 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each occurrence of R 4 , R 5 , R 6 , R 21 and R 22 independently represents hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof;

any two adjacent R 4 , R 5 , R 6 , R 7 , or a combination thereof may optionally together form a fused ring; and

each occurrence of n is independently an integer, valency permitting.

3. The compound of claim 1 , wherein one or more of the following conditions are true:

(i) at least one of Y 1 and Y 2 represents C, and at least one R 1 is represented by the following structure:

(ii) at least one R 2 is represented by the following structure:

(iii) at least one R 3 is represented by the following structure:

wherein

dashed lines indicate the bond to General Formula I;

X 13 , X 14 , X 15 , X 16 , X 17 , X 18 , X 19 , and X 20 , each independently represents C, N, Si, B, or P;

U 1 represents N, P, As, B, Al, or Bi, CR 21 , SiR 21 , GeR 21 , P═O, As═O, B, Bi═O, PR 21 R 22 , R 21 P═O, AsR 21 , R 21 As═O, S═O, SeO 2 , S═O, SeO 2 , R 21 Bi═O, or BiR 21 ;

each R 4 , R 5 and R 6 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each occurrence of R 4 , R 5 , R 6 , R 21 and R 22 independently represents hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof;

any two adjacent R 4 , R 5 , R 6 , or a combination thereof may optionally join to form a fused ring; and

each occurrence of n is independently an integer, valency permitting.

4. The compound of claim 1 , wherein at least one of X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , and X 12 represents N.

5. The compound of claim 1 , wherein at least two of X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , and X 12 represents N.

6. The compound of claim 1 , wherein at least one of X 5 , X 6 , X 7 , and X 8 represents N, and at least one of X 9 , X 10 , X 11 , and X 12 represents N.

7. The compound of claim 1 , wherein the compound is represented by General Formula IV, General Formula V, or General Formula VI:

wherein X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , and X 12 each independently represents C, N, Si, B, or P;

Y 1 and Y 2 each independently represent C, N, Si, B, or P;

each occurrence of n is independently an integer, valency permitting; and

each occurrence of R 1 , R 2 , and R 3 independently represents hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof; and

any two adjacent R 1 , R 2 , R 3 , or a combination thereof may optionally together form a fused ring.

8. The compound of claim 1 , wherein the compound is represented by one of the following structures:

wherein X 1 , X 2 , X 3 , X 4 , X 3 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 , X 19 , X 20 , X 21 , X 22 , X 23 , X 24 , X 25 , X 26 , X 27 , and X 28 each independently represents C, N, Si, B, or P;

Y 1 and Y 2 each independently represents C, N, Si, B, or P

each occurrence of n is independently an integer, valency permitting;

each U 1 and U 2 represents, valency permitting, O, S, Se, N, P, As, B, Al, Bi, P═O, As═O, Bi═O, CR 21 , CR 21 R 22 , C═O, SiR 21 , SiR 21 R 22 , GeR 21 , GeR 21 R 22 , NR 21 , PR 21 , PR 21 R 22 , R 21 P═O, AsR 21 , R 21 As═O, S═O, SeO 2 , S═O, SeO 2 , BR 21 , BR 21 R 22 , AlR 21 , AlR 21 R 22 , R 21 Bi═O, or BiR 21 ,

each occurrence of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 21 and R 22 independently represents hydrogen, deuterium, halogen, hydroxyl, thiol, nitro, cyano, nitrile, isonitrile, sulfinyl, mercapto, sulfo, carboxyl, hydrazino; substituted or unsubstituted: aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, amino, monoalkylamino, dialkylamino, monoarylamino, diarylamino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, ureido, phosphoramide, silyl, polymeric; or any conjugate or combination thereof.

9. The compound of claim 1 , wherein the compound is represented by one of the following structures:

wherein each U 1 and U 2 independently represents, valency permitting, N, NPh, S, O, S═O, SO 2 , P═O, Se═O, CPh 2 , or CMe 2 , where Me is methyl and Ph is phenyl.

10. An organic light emitting diode comprising the compound of claim 1 .

11. A light emitting device comprising the organic light emitting diode of claim 10 .

12. An organic light emitting diode comprising the compound of claim 2 .

13. A light emitting device comprising the organic light emitting diode of claim 12 .

14. An organic light emitting diode comprising the compound of claim 3 .

15. An organic light emitting diode comprising the compound of claim 7 .

16. A light emitting device comprising the organic light emitting diode of claim 15 .

17. An organic light emitting diode comprising the compound of claim 8 .

18. A light emitting device comprising the organic light emitting diode of claim 17 .

19. An organic light emitting diode comprising the compound of claim 9 .

20. A light emitting device comprising the organic light emitting diode of claim 19 .