Electron-transporting materials and processes for making the same
View Patent ↗Compound of formula C is made by reacting a compound of formula A with an pyridyl boronic acid or pyridyl borate ester to form a compound of formula B; and combining the compound of formula B with a pyridyl dihalide to form the compound of C; wherein R 3 , R 4 , R 5 , R 6 and R 7 are, independently at each occurrence, a C 1 -C 20 aliphatic radical, a C 3 -C 20 aromatic radical, or a C 3 -C 20 cycloaliphatic radical; X is, independently at each occurrence, CH or N; Y is chloro or bromo; Z is bromo or iodo; and when Y is bromo, Z is iodo; d, e, and g are, independently at each occurrence, an integer ranging from 0-4; f is an integer ranging from 0-2; and h is an integer ranging from 0-3.
1. A process comprising:
reacting a compound of formula A with a pyridyl boronic acid or pyridyl borate ester to form a compound of formula B; and
combining the compound of formula B with a pyridyl dihalide to form a compound of formula C;
wherein
R 3 , R 4 , R 5 , R 6 and R 7 are, independently at each occurrence, a C 1 -C 20 aliphatic radical, a C 3 -C 20 aromatic radical, or a C 3 -C 20 cycloaliphatic radical;
X is, independently at each occurrence, CH or N;
Y is chloro or bromo;
Z is bromo or iodo; and when Y is bromo, Z is iodo;
d, e, and g are, independently at each occurrence, an integer ranging from 0-4;
f is an integer ranging from 0-2; and
h is an integer ranging from 0-3.
2. The process of claim 1 , wherein the compound of formula A is of formula
3. The process of claim 1 , wherein the compound of formula A is of formula
4. The process of claim 1 , wherein the pyridyl boronic acid or pyridyl borate ester is
5. The process of claim 1 , wherein the compound of formula B is
6. The process of claim 1 , wherein the compound of formula B is
7. The process of claim 1 , wherein the pyridyl dihalide is
8. The process of claim 1 , additionally comprising combining the compound of formula B with a borane esterification reagent before combining with the pyridyl dihalide.
9. The process of claim 1 , additionally comprising combining the pyridyl dihalide with a borane esterification reagent before reacting with the compound of formula B.
10. The process of any of claim 8 , wherein the borane esterification reagent is pinacolate diborane.
11. The process of claim 1 , wherein the compound of formula C is
12. The process of claim 1 , wherein the compound of formula C is
13. A compound of formula C produced by reacting a compound of formula A with an pyridyl boronic acid or pyridyl borate ester to form a compound of formula B; and
combining the compound of formula B with a pyridyl dihalide to form the compound of C;
wherein
R 3 , R 4 , R 5 , R 6 and R 7 are, independently at each occurrence, a C 1-C 20 aliphatic radical, a C 3 -C 20 aromatic radical, or a C 3 -C 20 cycloaliphatic radical;
X is, independently at each occurrence, CH or N;
Y is chloro or bromo;
Z is bromo or iodo; and when Y is bromo, Z is iodo;
d, e, and g are, independently at each occurrence, an integer ranging from 0-4;
f is an integer ranging from 0-2; and
h is an integer ranging from 0-3.
14. The compound of claim 13 , wherein the compound of formula A is of formula
15. The compound of claim 13 , wherein the compound of formula A is of formula
16. The compound of claim 13 , wherein the pyridyl boronic acid or pyridyl borate ester is
17. The compound of claim 13 , wherein the compound of formula B is
18. The compound of claim 13 , wherein the compound of formula B is
19. The compound of claim 13 , wherein the pyridyl dihalide is
20. The compound of claim 13 , additionally comprising combining the compound of formula B with a borane esterification reagent before combining with the pyridyl dihalide.
21. The compound of claim 13 , additionally comprising combining the pyridyl dihalide with a borane esterification reagent before reacting with compound B.
22. The compound of any of claim 20 , wherein the borane esterification reagent is pinacolate diborane.
23. The compound of claim 13 , being of formula
24. The compound of claim 13 , being of formula