Organic compound, light-emitting element, light-emitting device, electronic device, and lighting device
A novel substance with which an increase in life and emission efficiency of a light-emitting element can be achieved is provided. A carbazole compound having a structure represented by General Formula (G1) is provided. Note that a substituent which makes the HOMO level and the LUMO level of a compound in which a bond of the substituent is substituted with hydrogen deep and shallow, respectively is used as each of substituents in General Formula (G1) (R 1 , R 2 , Ar 3 , and α 3 ). Further, a subsistent which makes the band gap (Bg) and the T1 level of a compound in which a bond of the substituent is substituted with hydrogen wide and high is used as each of the substituents in General Formula (G1) (R 1 , R 2 , Ar 3 , and α 3 ).
1. A method for synthesizing an organic compound, of Formula (G1), the method including:
conducting a reaction according to the following scheme (A-3):
conducting a reaction according to the following scheme (A-4):
and
conducting a reaction according to the following scheme (A-5):
wherein R 1 represents any one of an alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylenyl group, and a substituent represented by General Formula (G1-1);
wherein R 2 represents any one of hydrogen, an alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, and a substituent represented by General Formula (G1-2);
wherein α 1 to α 3 independently represent an unsubstituted phenylene group or an unsubstituted biphenyldiyl group,
wherein Ar 1 and Ar 2 independently represent any one of an alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, and a substituted or unsubstituted triphenylenyl group,
wherein Ar 3 represents any one of a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, and a substituted or unsubstituted triphenylenyl group,
wherein X 2 to X 4 independently represent halogen, and
wherein B 2 and B 3 independently represent boronic acid or dialkoxyboron.
2. The method according to claim 1 , wherein R 1 represents any one of the following structures:
3. The method according to claim 1 , wherein R 2 represents any one of the following structures:
4. The method according to claim 1 , wherein α 3 represents any one of the following structures:
5. The method according to claim 1 , wherein Ar 1 and Ar 2 independently represent any one of the following structures:
6. The method according to claim 1 , wherein Ar 3 represents any one of the following structures:
7. The method according to claim 1 , wherein the boron compound is trimethyl borate or triethyl borate.
8. The method according to claim 1 , wherein X 2 to X 4 independently are bromine or iodine.
9. The method according to claim 1 , wherein a reactivity of X 3 is higher than a reactivity of X 4 .
10. The method according to claim 9 , wherein X 3 is iodine and X 4 is bromine.
11. The method according to claim 1 , wherein the Formula (a4) is the following structure:
12. The method according to claim 1 , wherein the Formula (a5) is the following structure:
13. The method according to claim 12 , wherein the Formula (a6) is any one of the following structures:
14. The method according to claim 1 , wherein the Formula (a7) is any one of the following structures:
15. A method for synthesizing an organic compound of Formula (G1), the method including:
conducting a reaction according to the following scheme (B-1):
wherein R 1 represents any one of an alkyl group having 1 to 12 carbon atoms, an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, an unsubstituted triphenylenyl group, and a substituent represented by General Formula (G1-1);
wherein R 2 represents any one of hydrogen, an alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, and a substituent represented by General Formula (G1-2);
wherein α 1 to α 3 independently represent an unsubstituted phenylene group or an unsubstituted biphenyldiyl group,
wherein Ar 1 represents any one of an alkyl group having 1 to 12 carbon atoms, an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, and an unsubstituted triphenylenyl group,
wherein Ar 2 represents any one of an alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, and a substituted or unsubstituted triphenylenyl group,
wherein Ar 3 represents any one of a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, and a substituted or unsubstituted triphenylenyl group,
wherein X 2 represents halogen, and
wherein B 4 represents boronic acid or dialkoxyboron.
16. The method according to claim 15 , wherein R 1 represents any one of the following structures:
17. The method according to claim 15 , wherein R 2 represents any one of the following structures:
18. The method according to claim 15 , wherein α 3 represents any one of the following structures:
19. The method according to claim 15 , wherein Ar 1 and Ar 2 independently represent any one of the following structures:
20. The method according to claim 15 , wherein Ar 3 represents any one of the following structures:
21. The method according to claim 15 , wherein X 2 is bromine or iodine.
22. The method according to claim 15 , wherein the Formula (a4) is the following structure:
23. The method according to claim 22 , wherein the Formula (a9) is the following structure: