Intermediate for heteroacene compound and synthetic method of heteroacene compound using its intermediate

Patent metadata

Field	Value
Publication number	US-9954183-B2
Application number	US-201615293873-A
Country	US
Kind code	B2
Filing date	Oct 14, 2016
Priority date	Oct 21, 2015
Publication date	Apr 24, 2018
Grant date	Apr 24, 2018

Abstract

An intermediate of a heteroacene compound is represented by Chemical Formula 1.

First claim

What is claimed is:

1. An intermediate of a heteroacene compound represented by Chemical Formula 3-1 1:

wherein, in Chemical Formula 3-1,
Z is one of an ethenylene group and an ethynylene group,
each of X 1 and X 2 is independently one of O, S, Se, and Te,
each X 3 and X 4 are independently one of O, S, Se, Te, N—R x , and C(R y )—C(R z ), wherein each of R x , R y and R z is independently one of hydrogen and a linear or branched C 1 to C 10 alkyl group, and
each of L 1 and L 2 is independently one of functional groups of Chemical Formula A and Chemical Formula B,

wherein, in Chemical Formula A,
each of R 1 , R 2 , and R 3 is independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a substituted or unsubstituted C 3 to C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 3 to C 30 heteroaryl group;
R 4 is one of hydrogen and a methyl group,
R 5 is one of a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 6 to C 30 aryloxy group, and an amine group (NR x R y , wherein each of R x and R y is independently one of hydrogen, a C 1 to C 30 alkyl group, and a C 6 to C 30 aryl group), and
* indicates a linking position to X 1 and X 2 ,

wherein, in Chemical Formula B,
each of R 1 , R 2 , and R 3 is independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a substituted or unsubstituted C 3 to C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 3 to C 30 heteroaryl group,
R 4 is one of hydrogen and a methyl group,
each of R 5a and R 5b is independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 6 to C 30 aryloxy group, and an amine group (NR x R y , wherein each of R x and R y is independently one of hydrogen, a C 1 to C 30 alkyl group, and a C 6 to C 30 aryl group), and
* indicates a linking position to X 1 and X 2 .

2. The intermediate of claim 1 , wherein each of the L 1 and L 2 groups is independently one of functional groups represented by Chemical Formula A-1, Chemical Formula A-2, and Chemical Formula A-3:

wherein, in Chemical Formula A-1,
each of R 1a , R 2a , and R 3a is independently one of hydrogen, a C 1 to C 6 alkyl group, a C 3 to C 10 cycloalkyl group, a C 3 to C 10 heterocycloalkyl group, a C 6 to C 10 aryl group, and a C 3 to C 10 heteroaryl group,
R 4a is one of hydrogen and a methyl group,
R 5a is one of a substituted or unsubstituted C 1 to C 10 alkyl group and a substituted or unsubstituted C 6 to C 10 aryl group, and
* indicates a linking position to X 1 and X 2 ,

wherein, in Chemical Formula A-2,
each of R 1a , R 2a , and R 3a is independently one of hydrogen, a C 1 to C 6 alkyl group, a C 3 to C 10 cycloalkyl group, a C 3 to C 10 heterocycloalkyl group, a C 6 to C 10 aryl group, and a C 3 to C 10 heteroaryl group,
R 4a is one of hydrogen and a methyl group,
R 5a is one of a substituted or unsubstituted C 1 to C 10 alkyl group and a substituted or unsubstituted C 6 to C 10 aryl group, and
* indicates a linking position to X 1 and X 2 , and

wherein, in Chemical Formula A-3,
each of R 1a , R 2a , and R 3a is independently one of hydrogen, a C 1 to C 6 alkyl group, a C 3 to C 10 cycloalkyl group, a C 3 to C 10 heterocycloalkyl group, a C 6 to C 10 aryl group and a C 3 to C 10 heteroaryl group,
R 4a is one of hydrogen and a methyl group,
each of R 5a and R 5b is independently one of a substituted or unsubstituted C 1 to C 10 alkyl group and a substituted or unsubstituted C 6 to C 10 aryl group, and
* indicates a linking position to X 1 and X 2 .

3. The intermediate of claim 1 , wherein in the Chemical Formula 3-1, a hydrogen of each aromatic ring is replaced by a substituent selected from a C 1 to C 30 linear or branched alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 2 to C 30 heteroacyl group, a substituted or unsubstituted C7 to C 30 arylalkyl group, a substituted or unsubstituted C 2 to C 30 heteroarylalkyl group, a substituted or unsubstituted C 2 to C 30 alkylheteroaryl group, a substituted or unsubstituted C5 to C 30 cycloalkyl group and a substituted or unsubstituted C 2 to C 30 heterocycloalkyl group.

4. A synthetic method of a heteroacene compound comprising:
forming a chalcogenophene ring by reacting an intermediate of a heteroacene compound represented by Chemical Formula 3-1 with a base material:

wherein, in Chemical Formula 3-1,
Z is one of an ethenylene group and an ethynylene group,
each of X 1 and X 2 is independently one of O, S, Se, and Te,
each of X 3 , and X 4 are independently one of O, S, Se, Te, N—R x , and C(R y )—C(R z ), wherein each of R x , R y and R z is independently one of hydrogen and a linear or branched C 1 to C 10 alkyl group, and
each of L 1 and L 2 is independently one of functional groups of Chemical Formula A and Chemical Formula B,

wherein, in Chemical Formula A,
each of R 1 , R 2 , and R 3 is independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a substituted or unsubstituted C 3 to C 30 heterocycloalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, and a substituted or unsubstituted C 3 to C 30 heteroaryl group,
R 4 is one of hydrogen and a methyl group,
R 5 is a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 1 to C 30 alkoxy group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 6 to C 30 aryloxy group, and an amine group (NR x R y , wherein each of R x and R y is independently one of hydrogen, a C 1 to C 30 alkyl group, and a C 6 to C 30 aryl group), and
* indicates a linking position to X 1 and X 2 ,

wherein, in Chemical Formula B,
each of R 1 , R 2 , and R 3 is independently one of hydrogen, a substituted or unsubstituted C 1 to C 30 alkyl group, a su

Assignees

• Samsung Electronics Co Ltd

Inventors

• Miyazaki Eigo
• Park Jeong Il
• Lee Eun Kyung

Classifications

• H01L51/0541

  Electricity · mapped topic

• C07D517/22

  in which the condensed system contains four or more hetero rings · CPC title

• H01L51/5012

  Electricity · mapped topic

• C07D345/00 Primary

  Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms · CPC title

• H01L51/0558

  Electricity · mapped topic