Amino fluorene polymer and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-10158080-B2
Application number	US-201615251312-A
Country	US
Kind code	B2
Filing date	Aug 30, 2016
Priority date	Sep 1, 2015
Publication date	Dec 18, 2018
Grant date	Dec 18, 2018

Abstract

An amino fluorene polymer including a first repeating unit represented by Formula 1:

wherein, in Formula 1, A, F, F′, m1, n1, n2, R 1 , R 2 , R 3 , and R 4 are the same as described in the specification.

First claim

What is claimed is:

1. An amino fluorene polymer comprising at least two first repeating units represented by Formula 1:

wherein, in Formula 1,
R 1 to R 3 are each independently selected from a hydrogen atom, a substituted or unsubstituted C 1 -C 10 alkyl group, and a substituted or unsubstituted C 6 -C 30 aryl group;
m1 is an integer from 1 to 20;
F and F′ are each independently selected from a substituted or unsubstituted azafluorenylene group and a substituted or unsubstituted fluorenylene group;
n1 and n2 are each independently selected from 1 and 2;
A is a group represented by Formula 2;
R 4 is selected from a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 3 -C 16 cycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 3 -C 16 cycloalkoxy group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 7 -C 40 aralkyl group, a substituted or unsubstituted C 5 -C 30 heteroaryl group, —Si(Q 1 )(Q 2 )(Q 3 ), and —N(Q 1 )(Q 2 );

wherein, in Formula 2,
L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 3 -C 16 cycloalkylene group, a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted C 1 -C 20 oxyalkylene group, a substituted or unsubstituted C 3 -C 16 oxycycloalkylene group, a substituted or unsubstituted C 6 -C 30 oxyarylene group, a substituted or unsubstituted C 7 -C 40 aralkylene group, a substituted or unsubstituted C 5 -C 30 heteroarylene group, —Si(Q 4 )(Q 5 )-, and —N(Q 4 )-;
n3 and n4 are each independently selected from 1 and 2;
Ar 1 is selected from a hydrogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 3 -C 16 cycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 3 -C 16 cycloalkoxy group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 7 -C 40 aralkyl group, a substituted or unsubstituted C 5 -C 30 heteroaryl group, and —N(Q 6 )(Q 7 );
wherein, Ar 1 optionally binds to F, F′, L 1 , or L 2 to form a ring;
Q 1 to Q 7 are each independently selected from a hydrogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, and a substituted or unsubstituted C 6 -C 30 aryl group; and
* is a binding site to an adjacent atom.

2. The amino fluorene polymer of claim 1 , wherein R 1 to R 3 are each independently selected from a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, and an n-butyl group.

3. The amino fluorene polymer of claim 1 , wherein F and F′ are each independently a group represented by Formula 3:

wherein, in Formula 3,
R 5 to R 8 are each independently selected from a binding site, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 3 -C 16 cycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 3 -C 16 cycloalkoxy group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 7 -C 40 aralkyl group, a substituted or unsubstituted C 5 -C 30 heteroaryl group, —Si(Q 1 )(Q 2 )(Q 3 ), and —N(Q 1 )(Q 2 );
wherein, adjacent groups selected from R 5 to R 8 are optionally linked to one another to form a ring;
two groups selected from R 5 to R 8 are binding sites to adjacent atoms;
Q 1 to Q 3 are each independently selected from a hydrogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, and a substituted or unsubstituted C 6 -C 30 aryl group;
a and b are each independently selected from 1, 2, 3, and 4; and
Y 1 to Y 8 are each independently a carbon atom or a nitrogen atom.

4. The amino fluorene polymer of claim 3 , wherein R 5 to R 8 are each independently selected from
a single bond representing a binding site, hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a tert-pentyl group, a neopentyl group, a 1,2-dimethylpropyl group, an n-hexyl group, an iso-hexyl group, a 1,3-dimethyl butyl group, a 1-isopropyl propyl group, a 1,2-dimethyl butyl group, an n-heptyl group, a 1,4-dimethyl pentyl group, a 3-ethyl pentyl group, a 2-methyl-1-isopropyl propyl group, a 1-ethyl-3-methyl butyl group, an n-octyl group, a 2-ethyl hexyl group, a 3-methyl-1-isopropyl butyl group, a 2-methyl-1-isopropyl group, a 1-tert-butyl-2-methyl propyl group, an n-nonyl group, a 3,5,5-trimethyl hexyl group, an n-decyl group, an iso-decyl group, an n-undecyl group, a 1-methyl decyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, an n-nonadecyl group, an n-eicosyl group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a triazinyl group, a furanyl group, and a thiophenyl group;
a methyl group, an ethyl group, and an n-propyl group, each substituted with at least one selected from —F, a phenyl group, and a naphthyl group;
a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a triazinyl group, a furanyl group, and a thiophenyl group, each substituted with at least one selected from a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-octyl group, a phenyl group, a naphthyl group, a phenyl group substituted with a methyl group, and a phenyl group substituted with a tert-butyl group;
wherein, adjacent groups selected from R 5 to R 8 are optionally linked to one another to form a ring; and
wherein two groups selected from R 5 to R 8 are binding sites to adjacent atoms.

5. The amino fluorene polymer of claim 1 , wherein F and F′ are each independently selected from groups represented by Formulae 4-1 to 4-58:

wherein, in Formulae

Assignees

• Samsung Electronics Co Ltd

Inventors

• Shibata Katsunori
• Ishii Norihito

Classifications

• C08F212/32

  containing two or more rings · CPC title

• C08F212/26

  Nitrogen · CPC title

• C08G2261/76

  crosslinking · CPC title

• C08F12/28

  Amines · CPC title

• C07C13/567

  with a fluorene or hydrogenated fluorene ring system · CPC title