Fullerene derivatives and photoelectric devices and image sensors

Patent metadata

Field	Value
Publication number	US-10249823-B2
Application number	US-201715822400-A
Country	US
Kind code	B2
Filing date	Nov 27, 2017
Priority date	Jul 12, 2017
Publication date	Apr 2, 2019
Grant date	Apr 2, 2019

Abstract

A fullerene derivative may be included in photoelectric devices and image sensor. Optical absorption characteristics of a thin film including the fullerene derivative may be shifted toward a short wavelength compared with those of the thin film including the unsubstituted C60 fullerene, for example, a thin film including the fullerene derivative may be associated with a peak absorption wavelength (λ max ) that is be shorter than that of a thin film including the unsubstituted C60 fullerene.

First claim

What is claimed is:

1. A compound, comprising:
a fullerene derivative represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
R a is hydrogen or a C1 to C10 alkyl group,
R 1 to R 5 are independently one of
a substituted or unsubstituted C1 to C10 alkyl group, or
a substituted or unsubstituted C6 to C12 aryl group, and

at least one of R 1 to R 5 is
a C1 to C10 alkyl group substituted with at least one of a fluorine and a cyano group, or
a C6 to C12 aryl group substituted with at least one of a fluorine and a cyano group.

2. The compound of claim 1 , wherein the fullerene derivative is a compound that is configured to be vacuum-deposited based on sublimation.

3. The compound of claim 2 , wherein the fullerene derivative is configured to, at a pressure of 1 Pa or less,
have an about 10 wt % weight loss relative to an initial weight at a temperature of less than or equal to about 450° C.,
have an about 50 wt % weight loss relative to an initial weight at a temperature of less than or equal to about 510° C., and
have an about 90 wt % weight loss relative to an initial weight at a temperature of less than or equal to about 600° C.

4. The compound of claim 1 , wherein the fullerene derivative has a LUMO energy level of about 3.7 eV to about 5.0 eV and a HOMO energy level of about 5.8 eV to about 7.0 eV.

5. The compound of claim 1 , wherein R 1 to R 5 are independently one of
a C1 to C10 alkyl group substituted with at least one of a fluorine and a cyano group, or
a C6 to C12 aryl group substituted with at least one of a fluorine and a cyano group.

6. The compound of claim 1 , wherein the fullerene derivative is represented by one of Chemical Formulae 1a to 1l:

wherein, in Chemical Formulae 1a and 1b,
R 1 to R 3 are independently one of hydrogen or a fluorine and at least one of R 1 to R 3 is a fluorine.

7. A thin film comprising the compound of claim 1 .

8. The thin film of claim 7 , wherein the thin film is associated with a peak absorption wavelength (λ max ) that is shorter than a peak absorption wavelength (λ max ) of a thin film including C60 fullerene.

9. A photoelectric device, comprising:
a first electrode and a second electrode facing each other, and
an organic layer between the first electrode and the second electrode
wherein the organic layer includes a fullerene derivative represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
R a is hydrogen or a C1 to C10 alkyl group,
R 1 to R 5 are independently one of a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group, and
at least one of R 1 to R 5 is
a C1 to C10 alkyl group substituted with at least one of a fluorine and a cyano group, or
a C6 to C12 aryl group substituted with at least one of a fluorine and a cyano group.

10. The photoelectric device of claim 9 , wherein R 1 to R 5 of Chemical Formula 1 are independently one of
a C1 to C10 alkyl group substituted with at least one of a fluorine and a cyano group, or
a C6 to C12 aryl group substituted with at least one of a fluorine and a cyano group.

11. The photoelectric device of claim 9 , wherein the fullerene derivative is represented by one of Chemical Formulae 1a to 1l:

wherein, in Chemical Formula 1a,
R 1 to R 3 is hydrogen or a fluorine, and
at least one of R 1 to R 3 is a fluorine.

12. The photoelectric device of claim 9 , wherein
the organic layer includes an active layer,
the active layer includes a p-type semiconductor and an n-type semiconductor that at least partially comprise a pn junction, and
the n-type semiconductor includes the fullerene derivative.

13. The photoelectric device of claim 12 , wherein the p-type semiconductor and the n-type semiconductor are configured to be co-deposited based on sublimation.

14. The photoelectric device of claim 12 , wherein the fullerene derivative has a LUMO energy level of about 3.7 eV to about 5.0 eV and a HOMO energy level of about 5.8 eV to about 7.0 eV.

15. The photoelectric device of claim 14 , wherein the p-type semiconductor has a LUMO energy level of about 3.0 eV to about 3.6 eV and a HOMO energy level of about 5.1 eV to about 5.7 eV.

16. The photoelectric device of claim 15 , wherein the p-type semiconductor is a light absorbing material having a core structure including an electron donating moiety, a pi conjugation linking group, and an electron accepting moiety.

17. The photoelectric device of claim 16 , wherein the p-type semiconductor includes a compound represented by Chemical Formula 2:

wherein, in Chemical Formula 2,
X is Se, Te, SO, SO 2 , or SiR a R b ,
EDG is an electron donating group,
EAG is an electron accepting group, and
R 11 , R 12 , R a , and R b are independently one of hydrogen or a monovalent substituent.

18. An electronic device comprising the photoelectric device of claim 9 .

19. An image sensor comprising the photoelectric device of claim 9 .

Assignees

• Samsung Electronics Co Ltd

Inventors

• Shibuya Hiromasa
• Yagi Tadao
• Sakurai Rie
• Choi Yeong Suk
• Matsuo Yutaka

Classifications

• H01L27/307

  Electricity · mapped topic

• C07C23/46

  with more than three condensed rings · CPC title

• H01L51/0047 Primary

  Electricity · mapped topic

• C07C25/18 Primary

  Polycyclic aromatic halogenated hydrocarbons · CPC title

• H01L51/001

  Electricity · mapped topic