Fullerene derivatives and organic electronic device comprising fullerene derivatives

Patent metadata

Field	Value
Publication number	US-10693073-B2
Application number	US-201515110308-A
Country	US
Kind code	B2
Filing date	Jan 8, 2015
Priority date	Jan 8, 2014
Publication date	Jun 23, 2020
Grant date	Jun 23, 2020

Abstract

The present specification relates to an organic electronic device including a fullerene derivative.

First claim

The invention claimed is:

1. A fullerene derivative of Chemical Formula 1:

wherein:
n is an integer of 1 to 5;
when n is 2 or greater, structures within a parenthesis are the same as or different from each other;
Cn is fullerene of C 60 to C 120 ;
R1 to R6 are the same as or different from each other, and each is independently hydrogen, a halogen group, a nitro group, a cyano group, a carboxylic acid group, a hydroxyl group, a substituted or unsubstituted carbonyl group, a sulfo group (—SO 3 H), a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted thioester group, a substituted or unsubstituted amide group, a substituted or unsubstituted ether group, a substituted or unsubstituted sulfonyl group (—SO 2 —), a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted heteroarylalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroring group, or adjacent substituents bond to each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heteroring;
only one of R1 to R6 is

o is an integer of 1 to 3, and when o is an integer of 2 or greater, two or more Ls are the same as or different from each other;
L is an unsubstituted alkylene; and
R is hydrogen, a carboxylic acid group, a substituted or unsubstituted carbonyl group, an unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted thioester group, a substituted or unsubstituted amide group, a substituted or unsubstituted sulfonyl group (—SO 2 —), a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroring group,
when R is a substituted carbonyl group substituted with a substituted alkyl group, the substituted alkyl group of the substituted carbonyl group is substituted with one or more substituents selected from the group consisting of a halogen group, a nitro group, a cyano group, a hydroxyl group, a carbonyl group, a sulfo group, an allyl group, an alkoxy group, a cycloalkyl group, an alkenyl group, an ester group, an ether group, a sulfonyl group, a sulfoxy group, an arylalkyl group, an aryl group, and a heteroring group,
wherein when one of R5 and R6 is unsubstituted alkyl and the other one of R5 and R6 is hydrogen, R3 and R4 are each hydrogen, one of R1 and R2 is hydrogen and the other one of R1 and R2 is

L is an unsubstituted alkylene, and o is 1, R is a carboxylic acid group, a substituted or unsubstituted carbonyl group, an unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted thioester group, a substituted or unsubstituted amide group, a substituted or unsubstituted sulfonyl group (—SO 2 —), a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroring group.

2. The fullerene derivative of claim 1 , wherein the fullerene derivative of Chemical Formula 1 is a fullerene derivative of Chemical Formula 2 or 3:

wherein
R, Cn, n, o, L and R1 to R6 are the same as for Chemical Formula 1.

3. The fullerene derivative of claim 1 , wherein the fullerene derivative of Chemical Formula 1 is a fullerene derivative of Chemical Formula 2-1 or Chemical Formula 3-1:

wherein:
Cn, n, o, L and R1 to R6 are the same as for Chemical Formula 1;
R7 and R8 are each independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted ether group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted arylalkyl group, substituted or unsubstituted cyclic ketone, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroring group; and
when R8 is a substituted alkyl group, the substituted alkyl group is substituted with one or more substituents selected from the group consisting of a halogen group, a nitro group, a cyano group, a hydroxyl group, a carbonyl group, a sulfo group, an allyl group, an alkoxy group, a cycloalkyl group, an alkenyl group, an ester group, an ether group, a sulfonyl group, a sulfoxy group, an arylalkyl group, an aryl group, and a heteroring group.

4. The fullerene derivative of claim 1 , wherein R is hydrogen, an unsubstituted alkyl group, or a substituted or unsubstituted carbonyl group.

5. The fullerene derivative of claim 3 , wherein R7 and R8 are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, substituted or unsubstituted cyclic ketone, or a substituted or unsubstituted heteroring group.

6. The fullerene derivative of claim 1 , wherein the fullerene derivative of Chemical Formula 1 is a fullerene derivative of Chemical Formulae 1-1-1, 1-1-2, and 1-1-4 to 1-1-30:

wherein
n is the same as for Chemical Formula 1.

7. An organic electronic device comprising:
a first electrode;
a second electrode provided opposite to the first electrode; and
one or more organic material layers provided between the first electrode and the second electrode,
wherein the one or more organic material layers include the fullerene derivative of claim 1 .

8. The organic electronic device of claim 7 , which is selected from the group consisting of an organic light emitting device, an organic solar cell, and an organic transistor.

9. The organic electronic device of claim 7 is an organic solar cell.

10. The organic electronic device of claim 9 , wherein the one or more organic material layers include a photoactive layer, the photoactive l

Assignees

• Lg Chemical Ltd

Inventors

• Bae Jaesoon
• Lee Jaechol
• Lee Jiyoung
• Choi Doowhan

Classifications

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K85/215

  comprising substituents, e.g. PCBM · CPC title

• C09K11/65 Primary

  containing carbon (in organic compounds C09K11/06) · CPC title

• H10K50/00

  Organic light-emitting devices (integrated devices or assemblies of multiple devices H10K59/00, H10K65/00; organic semiconductor lasers H01S5/36) · CPC title

• H10K85/113

  Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene · CPC title