Heteroaromatic compounds for organic electronics

Patent metadata

Field	Value
Publication number	US-10079346-B2
Application number	US-201515537522-A
Country	US
Kind code	B2
Filing date	Dec 16, 2015
Priority date	Dec 19, 2014
Publication date	Sep 18, 2018
Grant date	Sep 18, 2018

Abstract

The present invention provides compounds of formula (I) wherein X is O, S or NR 10 , wherein R 10 is H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl or C(0)-OR 11 , R 1 and R 11 are independently from each other selected from the group consisting of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, and substituted C 5-8 -cycloalkenyl, and an electronic device comprising the compounds as semiconducting material.

First claim

The invention claimed is:

1. A compound of formula (1):

wherein:
X is O, S or NR 10 ,
R 10 is H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl or C(O)—OR 11 ,
R 1 and R 11 are independently from each other selected from the group consisting of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, and substituted C 5-8 -cycloalkenyl,
R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are independently from each other selected from the group consisting of H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, substituted C 5-8 -cycloalkenyl, O—C 1-30 -alkyl, substituted O—C 1-30 -alkyl, S—C 1-30 -alkyl, substituted S—C 1-30 -alkyl, C 6-14 -aryl, substituted C 6-14 -aryl, 5 to 15 membered heteroaryl, substituted 5 to 15 membered heteroaryl and halogen,
or R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , or, R 8 and R 9 together with the C-atoms, to which they are connected, form a 6 to 10 membered aromatic ring system, substituted 6 to 10 membered aromatic ring system, 5 to 12 membered heteroaromatic ring system or a substituted 5 to 12 membered heteroaromatic ring system,
substituted C 1-30 -alkyl, substituted C 2-30 -alkenyl, substituted C 2-30 -alkynyl, substituted O—C 1-30 -alkyl and substituted S—C 1-30 -alkyl, at each occurrence, are C 1-30 -alkyl, C 2-30 -alkenyl, C 2-30 -alkynyl, O—C 1-30 -alkyl, respectively, S—C 1-30 -alkyl, which are substituted with at least one substituent independently selected from the group consisting of C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 12 membered heteroaryl, OR a , OC(O)—R a , OC(O)—OR a , OC(O)—NR a R b , C(O)—R a , C(O)—OR a , C(O)—NR a R b , C(O)—NR a —NR b R c , C(O)—NR a —OR b , C(O)—NR a —C(O)—R b , C(O)—NR a —C(O)—OR b , C(O)—SR a , NR a R b , NR a —NR b R c , NR a —C(O)R b , NR a —C(O)—OR b , NR a —C(O)—NR b R c , SR a , S—C(O)—R a , halogen, CN, and NO 2 ;
substituted C 5-8 -cycloalkyl, and substituted C 5-8 -cycloalkenyl, at each occurrence, are C 5-8 -cycloalkyl, respectively, C 5-8 -cycloalkenyl, which are substituted with at least one substituent independently selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 12 membered heteroaryl, OR a , OC(O)—R a , OC(O)—OR a , OC(O)—NR a R b , C(O)—R a , C(O)—OR a , C(O)—NR a R b , C(O)—NR a —NR b R c , C(O)—NR a —OR b , C(O)—NR a —C(O)—R b , C(O)—NR a —C(O)—OR b , C(O)—SR a , NR a R b , NR a —NR b R c , NR a —C(O)R b , NR a —C(O)—OR b , NR a —C(O)—NR b R c , SR a , S—C(O)—R a , halogen, CN, and NO 2 ;
substituted C 6-14 -aryl, substituted 5 to 15 membered heteroaryl, substituted 6 to 10 membered aromatic ring system, and substituted 5 to 12 membered heteroaromatic ring system, at each occurrence, are C 6-14 -aryl, 5 to 15 membered heteroaryl, 6 to 10 membered aromatic ring system, respectively, 5 to 12 membered heteroaromatic ring system, which are substituted with at least one substituent independently selected from the group consisting of C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, C 5-6 -cycloalkenyl, C 6-10 -aryl, 5 to 12 membered heteroaryl, OR a , OC(O)—R a , OC(O)—OR a , OC(O)—NR a R b , C(O)—R a , C(O)—OR a , C(O)—NR a R b , C(O)—NR a —NR b R c , C(O)—NR a —OR b , C(O)—NR a —C(O)—R b , C(O)—NR a —C(O)—OR b , C(O)—SR a , NR a R b , NR a —NR b R c , NR a —C(O)R b , NR a —C(O)—OR b , NR a C(O)—NR b R c , SR a , S—C(O)—R a , halogen, CN, and NO 2 ,
at least one CH 2 -group, but not adjacent CH 2 -groups, of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, substituted C 5-8 -cycloalkenyl, O—C 1-30 -alkyl, substituted O—C 1-30 -alkyl, S—C 1-30 -alkyl and substituted S—C 1-30 -alkyl, can be replaced by a linking group selected from the group consisting of O, S, NR 12 , CO, O—C(O), C(O)—O, O—C(O)—O, S—C(O), C(O)—S, NR 12 —C(O), C(O)—NR 12 , OC(O)—NR 12 and NR 12 —C(O)—O,
R 12 is H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl or C(O)—OR d , and
R a , R b , R c and R d are independently from each other and at each occurrence selected from the group consisting of H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-6 -cycloalkyl, C 5-6 -cycloalkenyl, C 6-10 -aryl, and 5 to 12 membered heteroaryl.

2. The compound of claim 1 , wherein:
X is O, S or NR 10 ,
R 10 is H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, or C(O)—OR 11 ,
R 1 and R 11 are independently from each other selected from the group consisting of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, and substituted C 5-8 -cycloalkenyl,
R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are independently from each other selected from the group consisting of H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, substituted C 5-8 -cycloalkenyl, O—C 1-30 -alkyl, substituted O—C 1-30 -alkyl, S—C 1-30 -alkyl, substituted S—C 1-30 -alkyl, C 6-14 -aryl, substituted C 6-14 -aryl, 5 to 15 membered heteroaryl, substituted 5 to 15 membered heteroaryl and halogen, or R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , or, R 8 and R 9 together with the C-atoms, to which they are connected, form a 6 to 10 membered aromatic ring system, substituted 6 to 10 membered aromatic ring system, 5 to 12 membered heteroaromatic ring system or a substituted 5 to 12 membered heteroaromatic ring system,
substituted C 1-30 -alkyl, substituted C 2-30 -alkenyl, substituted O—C 1-30 -alkyl and substituted S—C 1-30 -alkyl, at each occurrence, are C 1-30 -alkyl, C 2-30 -alkenyl, O—C 1-30 -alkyl, respectively, S—C 1-30 -alkyl, which are substituted with at least one substituent independently selected from the group consisting of C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 12 membered heteroaryl, OR a , OC(O)—R a , OC(O)—OR a , OC(O)—NR a R b , C(O)—R a , C(O)—OR a , C(O)—NR a R b , C(O)—NR a —NR b R c , C(O)—NR a —OR b , C(O)—NR a —C(O)—R b , C(O)—NR a —C(O)—OR b , C(O)—SR a , NR a R b , NR a —NR b R c , NR a —C(O)R b , NR a —C(O)—OR b , NR a —C(O)—NR b R c , SR a , S—C(O)—R a , halogen, CN, and NO 2 ;
substituted C 5-8 -cycloalkyl, and substituted C 5-8 -cycloalkenyl, at each occurrence, are C 5-8 -cycloalkyl, respectively, C 5-8 -cycloalkenyl, which are substituted with at least one substituent independently selected from the group consisting of C 1-20 -alkyl, C 5-6 -cycloalkyl, C 6-10 -aryl, 5 to 12 membered heteroaryl, OR a , OC(O)—R a , OC(O)—OR a , OC(O)—NR a R b , C(O)—R a , C(O)—OR a , C(O)—NR a R b , C(O)—NR a —NR b R c , C(O)—NR a —OR b , C(O)—NR a —C(O)—R b , C(O)—NR a —C(O)—OR b , C(O)—SR a , NR a R b , NR a —NR b R c , NR a —C(O)R b , NR a —C(O)—OR b , NR a —C(O)—NR b R c , SR a , S—C(O)—R a , halogen, CN, and NO 2 ;
substituted C 6-14 -aryl, substituted 5 to 15 membered heteroaryl, substituted 6 to 10 membered aromatic ring system, and substituted 5 to 12 membered heteroaromatic ring system, at each occurrence, are C 6-14 -aryl,

Assignees

• Basf Se

Inventors

• Yamato Hitoshi
• Tsuda Takuya
• Wu Chao
• Weitz Thomas
• Eustachi Michael
• Hemgesberg Maximilian

Classifications

• C07D513/14 Primary

  Ortho-condensed systems · CPC title

• H01L51/0071 Primary

  Electricity · mapped topic

• H01L51/0562

  Electricity · mapped topic

• H10D30/00

  Field-effect transistors [FET] (insulated-gate bipolar transistors H10D12/00) · CPC title

• C07D498/14

  Ortho-condensed systems · CPC title