Heterocyclic fluorescent dyes and method of production thereof

Patent metadata

Field	Value
Publication number	US-9893302-B2
Application number	US-201715414060-A
Country	US
Kind code	B2
Filing date	Jan 24, 2017
Priority date	Mar 6, 2013
Publication date	Feb 13, 2018
Grant date	Feb 13, 2018

Abstract

The invention relates to novel compounds of formula (III) that can be used as heterocyclic dyes of unique structure and properties. These compounds can be obtained in a three-step synthesis from simple substrates. The compounds according to the invention have excellent solubility in organic solvents and excellent film-forming properties. In addition, high efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the compounds according to the invention are used in organic field effect transistors, organic photovoltaics (solar cells) and photodiodes.

First claim

The invention claimed is:

1. A compound of formula

wherein
R 3 is hydrogen, halogen; cyano, C 1 -C 25 alkoxy, C 1 -C 25 alkyl substituted with one or
more halogen atoms; C 1 -C 25 alkyl

wherein
X is O, S, Se, or NR 4 , where R 4 is hydrogen, C 6 -C 18 aryl, C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, halogen, cyano, C 1 -C 18 alkoxy, C 1 -C 25 alkyl which may optionally be interrupted by one or more oxygen or sulfur atoms and may optionally be substituted by one or more halogen atoms, or C 7 -C 25 arylalkyl;
R 22 to R 25 and R 29 to R 33 represent independently of each other H, F, cyano, C 1 -C 25 alkoxy, C 1 -C 25 alkyl substituted with one or more halogen atoms; or C 1 -C 25 alkyl, and
R 26 is H, F, cyano, phenyl, C 1 -C 25 alkoxy, C 1 -C 25 alkyl substituted with one or more halogen atoms, or C 1 -C 25 alkyl;
R 99 , R 99′ , R 99″ and R 99* are independently of each other hydrogen, C 1 -C 25 alkyl, or C 1 -C 25 alkyl interrupted by one or more oxygen atoms; preferably C 3 -C 25 alkyl, or C 3 -C 25 alkyl which is interrupted by one or more oxygen atoms;
R 121 , R 122 , R 123 , R 124 and R 125 are independently of each other hydrogen, halogen, C 1 -C 18 alkoxy or C 1 -C 25 alkyl; preferably hydrogen; and
R 130 is hydrogen, C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, halogen; or C 1 -C 18 alkoxy; C 1 -C 25 alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms and/or is optionally substituted by one or more halogen atoms; or C 7 -C 25 arylalkyl.

2. The compound of claim 1 , wherein the compound is according formula IN-1.

3. The compound of claim 1 , wherein the compound is according formula IN-2.

4. The compound of claim 1 , wherein the compound is according formula IN-3.

5. The compound of claim 1 , wherein the compound is according formula IN-4.

6. The compound of claim 1 , wherein the compound is according formula IN-5.

7. The compound of claim 1 , wherein the compound is according formula IN-6.

8. The compound of claim 1 , wherein the compound is according formula IN-7.

9. The compound of claim 1 , wherein the compound is according formula IN-8.

10. The compound of claim 1 , wherein the compound is according formula IN-9.

11. The compound of claim 1 , wherein the compound is according formula IN-10.

12. The compound of claim 1 , wherein the compound is according formula IN-11.

13. The compound of claim 1 , wherein the compound is according formula IN-12.

14. The compound of claim 1 , wherein the compound is according formula IN-13.

15. The compound of claim 1 , wherein the compound is according formula IN-14.

16. The compound of claim 1 , wherein the compound is according formula IN-15.

17. The compound of claim 1 , wherein the compound is according formula IN-16.

18. The compound of claim 1 , wherein the compound is according formula IN-17.

Assignees

• Basf Se

Inventors

• Gryko Daniel T
• Grzybowski Marek

Classifications

• C09B57/004

  Diketopyrrolopyrrole dyes · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• H01L51/0508

  Electricity · mapped topic

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title