Aromatic AZA heterocycles, method of production and use of the material in organic electronics
View Patent ↗An electron transport material based on fused aromatic electron-deficient compounds. The accumulation of aromatic rings with an electron deficiency allows free-radical anions to be stabilized very efficiently in these systems.
1. A heteroaromatic compound having a chemical formula B, C, or D as shown below:
wherein each of R 1 and R 2 is independently selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, and a π-deficient aromatic compound; and
R 3 is aryl or alkyl.
2. The compound of claim 1 having a chemical formula C or D as shown in claim 1 , wherein R 3 is phenyl.
3. The compound of claim 1 having a chemical formula C or D as shown in claim 1 , wherein R 3 is methyl.
4. The compound of claim 1 having a chemical formula B or D as shown in claim 1 , wherein the π-deficient aromatic compound is selected from fused and unfused aromatic six-membered aza heterocyclic compounds with one or more nitrogen atoms.
5. The compound of claim 1 having a chemical formula B or D as shown in claim 1 , wherein the π-deficient aromatic compound is selected from five-membered π-deficient aromatic compounds having at least 3 heteroatoms.
6. The compound of claim 1 having a general chemical formula B as shown in claim 1 and a specific chemical formula A as shown below:
7. A process for preparing a heteroaromatic compound having a chemical formula B, C, or D as shown below:
wherein each of R 1 and R 2 is independently selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, and a π-deficient aromatic compound; and
R 3 is aryl or alkyl, wherein a compound of formula 4
is converted to the compound of formula B; or a compound of formula 7
is converted to the compound of formula C or D;
wherein the step of converting the compound of formula 7 to the compound of formula D comprises reacting the compound of formula 7 with a compound of formula R 1 R 2 C═O.
8. The process of claim 7 wherein
the compound of formula 4 is prepared by a process comprising: 1) reacting a compound of formula 1
with a compound of formula 2 1
to form a compound of formula 3;
and 2) converting the compound of formula 3 to the compound of formula 4
9. The process of claim 7 wherein the compound of formula 7 is prepared by a process comprising: 1) reacting a compound of formula 1
with a compound of formula 5
to form a compound of formula 6;
and 2) converting the compound of formula 6 to the compound of formula 7
10. An electronic device comprising an electronic transport component, wherein the electronic transport component comprises a compound of claim 1 .
11. The process of claim 7 wherein the step of converting the compound of formula 4 to the compound of formula B comprises dimerizing the compound of formula 4 or reacting the compound of formula 4 with a compound of formula R 1 R 2 C═O, wherein each of R 1 and R 2 is independently selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, and a π-deficient aromatic compound.
12. The process of claim 7 wherein the step of converting the compound of formula 7 to the compound of formula C comprises dimerizing the compound of formula 7.
13. The process of claim 8 wherein the compound of formula 3 is converted to the compound of formula 4 via hydrogenation and cyclization.
14. The process of claim 9 wherein the compound of formula 6 is converted to the compound of formula 7 via hydrogenation and cyclization.