Tetrasubstituted coronenes
Tetrasubstituted coronenes are provided. Also provided are electronic devices in which the active layer includes a tetrasubstituted coronene.
1. An electronic device comprising at least one layer comprising a compound having Formula I:
wherein:
R 1 -R 16 are independently selected from the group consisting of H, F, alkyl, aryl, fluoroalkyl, fluoroaryl, and E(R 9 ) 3 groups wherein E is Si, Ge, or Sn, wherein at least one of R 1 -R 4 , at least one of R 5 -R 8 , at least one of R 9 -R 12 and at least one of R 13 -R 16 is not H or F.
2. The device of claim 1 , wherein R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 are methyl, and R 2 , R 3 , R 6 , R 7 , R 10 , R 11 and R 15 are H.
3. The device of claim 1 , wherein R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 are H and R 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 are CF 3 .
4. The device of claim 1 , further comprising a diluent selected from the group consisting of poly(N-vinyl carbazole), polysilane, 4,4′-N,N′-dicarbazole biphenyl, and tertiary amines.
5. The device of claim 1 , further comprising a hole-transport layer comprising a compound selected from the group consisting of:
N,N′-diphenyl-N,N′-bis(3-methylphenyl)-[1,1′-biphenyl]4,4′-diamine; 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane; N,N′-bis(4-methylphenyl)-N,N′-bis(4-ethylphenyl)-[1,1′-(3,3′-dimethyl)biphenyl]-4,4′-diamine; tetrakis-(3-methylphenyl)-N,N,N′, N′-2,5-phenylenediamine; α-phenyl-4-N,N-diphenylaminostyrene; p-(diethylamino)benzaldehyde diphenylhydrazone; triphenylamine; bis[4-(N,N-diethylamino)-2-methylphenyl](4-methylphenyl)methane; 1-phenyl-3-[p-(diethylamino)styryl]-5-[p-(diethylamino)phenyl]pyrazoline; 1,2-trans-bis(9H-carbazol-9-yl)cyclobutane; N,N,N′,N′-tetrakis(4-methylphenyl)-(1,1′-biphenyl)-4,4′-diamine; porphyrinic compounds,
and combinations thereof.
6. The device of claim 1 , further comprising an electron-transport layer comprising a compound selected from the group consisting of tris(8-hydroxyquinolato)aluminum; 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline; 4,7-diphenyl-1,10-phenanthroline; 2-(4-biphenylyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole; 3-(4-biphenylyl)-4-phenyl-5-(4-t-butylphenyl)-1,2,4-triazole,
and combinations thereof.
7. A composition of Formula I
wherein:
R 1 -R 16 are independently selected from the group consisting of H, F, alkyl, aryl, fluoroalkyl, fluoroaryl, and E(R 9 ) 3 groups wherein E is Si, Ge, or Sn, wherein at least one of R 1 -R 4 , at least one of R 5 -R 8 , at least one of R 9 -R 12 and at least one of R 13 -R 16 is not H or F.
8. The composition of claim 7 , wherein the composition is selected from the group of compositions represented by Structures I and II: