Heteroacenes for organic electronics

Patent metadata

Field	Value
Publication number	US-9716237-B2
Application number	US-201515120981-A
Country	US
Kind code	B2
Filing date	Feb 18, 2015
Priority date	Feb 25, 2014
Publication date	Jul 25, 2017
Grant date	Jul 25, 2017

Abstract

The present invention provides compounds of formula 1 wherein X 1 and X 2 are independently from each other O, S or Se, and an electronic device comprising the compounds as semiconducting material.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
X 1 and X 2 are independently O, S, or Se, and
R 1 , R 2 , R 3 and R 4 are independently H, halogen, CN, NO 2 , a C 1-30 -alkyl, a C 2-30 -alkenyl, a C 2-30 -alkynyl, a C 6-14 -aryl, or a 5 to 14 membered heteroaryl,
wherein
the C 1-30 -alkyl, the C 2-30 -alkenyl and the C 2-30 -alkynyl are optionally substituted by one to five substituents which are independently selected from the group consisting of a C 6-10 -aryl, a 5 to 10 membered heteroaryl, OR a , OC(O)—R a , C(O)—OR a , C(O)—R a , NR a R b , NR a [C(O)R b ], N[C(O)R a ][C(O)R b ], halogen, CN and NO 2 ; and one or more CH 2 -groups, but not adjacent CH 2 -groups, of the C 1-30 -alkyl, the C 2-30 -alkenyl and the C 2-30 -alkynyl are optionally replaced by O or S, and
the C 6-14 -aryl and the 5 to 14 membered heteroaryl are optionally substituted by one to five substituents which are independently selected from the group consisting of a C 1-20 -alkyl, a C 2-20 -alkenyl, a C 2-20 -alkynyl, OR a , OC(O)—R a , C(O)—OR a , C(O)—R a , NR a R b , NR a [C(O)R b ], N[C(O)R a ][C(O)R b ], halogen, CN and NO 2 ,
wherein
R a and R b are independently selected from the group consisting of H, a C 1-20 -alkyl, a C 2-20 -alkenyl and a C 2-20 -alkynyl,
the C 1-20 -alkyl, the C 2-20 -alkenyl and the C 2-20 -alkynyl are optionally substituted by one to five substituents selected from the group consisting of phenyl, OR c , OC(O)—R c , C(O)—C(O)—R c , NR c R d , NR c [C(O)R d ], N[C(O)R c ][C(O)R d ], halogen, CN and NO 2 , and,
the C 6-10 -aryl and the 5 to 10 membered heteroaryl are optionally substituted by one to five substituents independently selected from the group consisting of a C 1-10 -alkyl, a C 2-10 -alkenyl, C 2-10 -alkynyl, OR c , OC(O)R c , C(O)—OR c , C(O)—R c , NR c R d , NR c [C(O)R d ], N[C(O)R c ][C(O)R d ], halogen, CN and NO 2 ,
wherein
R c and R d are independently selected from the group consisting of H, a C 1-10 -alkyl, a C 2-10 -alkenyl and a C 2-10 -alkynyl,
wherein
the C 1-10 -alkyl, the C 2-10 -alkenyl and the C 2-10 -alkynyl are optionally substituted by one to five substituents selected from the group consisting of halogen, CN and NO 2 .

2. The compound of claim 1 , wherein X 1 and X 2 are independently O or S.

3. The compound of claim 1 , wherein X 1 and X 2 are both S.

4. The compound of claim 1 , wherein R 1 , R 2 , R 3 and R 4 are independently H, the C 1-30 -alkyl, the C 2-30 -alkenyl, the C 2-30 -alkynyl, the C 6-14 -aryl or the 5 to 14 membered heteroaryl.

5. The compound of claim 1 , wherein R 1 , R 2 , R 3 and R 4 are independently H, the C 1-30 -alkyl, the C 6-14 -aryl or the 5 to 14 membered heteroaryl.

6. The compound of claim 1 , wherein R 2 and R 3 are H, and R 1 and R 4 are independently H or the C 1-30 -alkyl.

7. The compound of claim 1 , wherein R 2 and R 3 are H, and R 1 and R 4 are independently H or the C 1-30 -alkyl.

8. An electronic device, comprising
the compound of claim 1 .

9. The electronic device of claim 8 , wherein the electronic device is an organic field effect transistor (OFET).

10. A method for making a semiconductor device, the method comprising
incorporating the compound of claim 1 into the semiconductor device as a semiconductor material.

11. A method for conducting a current, the method comprising
applying a potential to the compound of claim 1 .

Assignees

• Basf Se

Inventors

• Jiao Chongjun
• Doi Iori
• Weitz Thomas
• Wu Chao
• Zhao Wyman
• Chua Szehui
• Becker Stefan
• Eustachi Michael

Classifications

• C07D495/14 Primary

  Ortho-condensed systems · CPC title

• H01L51/0074 Primary

  Electricity · mapped topic

• H01L51/0541

  Electricity · mapped topic

• H01L51/0558

  Electricity · mapped topic

• H10K85/6576 Primary

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title