Amine-based compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-10290820-B2
Application number	US-201414572701-A
Country	US
Kind code	B2
Filing date	Dec 16, 2014
Priority date	Jun 13, 2014
Publication date	May 14, 2019
Grant date	May 14, 2019

Abstract

An amine-based compound is represented by Formula 1.

Where, in Formula 1, at least one of R 1 , R 3 , R 8 , and R 10 is a group represented by Formula 2.

Where, in Formula 2, a1 is selected from 0, 1, 2 and 3. The remaining substituents of Formulae 1 and 2 are as described herein. An organic light-emitting device (OLED) includes the amine-based compound represented by Formula 1.

First claim

What is claimed is:

1. An amine-based compound represented by Formula 1:

wherein, in Formulae 1 and 2,
L 1 is selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 3 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 3 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic hetero-condensed polycyclic group;
a1 is selected from 0, 1, 2 and 3;
R 1 , R 3 , R 8 , and R 10 are each independently selected from a group represented by Formula 2, a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, and —Si(Q 3 )(Q 4 )(Q 5 );
at least one of R 1 , R 3 , R 8 , and R 10 is a group represented by Formula 2;
R 2 , R 4 to R 7 , R 9 , R 11 , and R 12 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, and —Si(Q 3 )(Q 4 )(Q 5 ),
wherein Q 3 to Q 5 are each independently selected from a C 1 -C 20 alkyl group, a phenyl group, and a naphthyl group;
R 21 and R 22 are each independently selected from a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group;
at least one substituent of the substituted C 3 -C 10 cycloalkylene group, substituted C 3 -C 10 heterocycloalkylene group, substituted C 3 -C 10 cycloalkenylene group, substituted C 3 -C 10 heterocycloalkenylene group, substituted C 6 -C 60 arylene group, substituted C 1 -C 60 heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic hetero-condensed polycyclic group, substituted C 1 -C 60 alkyl group, substituted C 2 -C 60 alkenyl group, substituted C 2 -C 60 alkynyl group, substituted C 1 -C 60 alkoxy group, substituted C 3 -C 10 cycloalkyl group, substituted C 3 -C 10 heterocycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted C 3 -C 10 heterocycloalkenyl group, substituted C 6 -C 60 aryl group, substituted C 6 -C 60 aryloxy group, substituted C 6 -C 60 arylthio group, substituted C 1 -C 60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic hetero-condensed polycyclic group is selected from:
a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy, a C 6 -C 60 arylthio, a C 1 -C 60 group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic hetero-condensed polycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), and —B(Q 16 )(Q 17 );
a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group;
a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 a alkoxy group, a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic hetero-condensed polycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), and —B(Q 26 )(Q 27 ); and
—N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ), and —B(Q 36 )(Q 37 ),

wherein Q 1 to Q 7 , Q 11 to Q 17 , Q 21 to Q 27 , and Q 31 to Q 37 are each independently selected from a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group, and
wherein:
R 3 and R 10 are each independently a group represented by Formula 2;
R 3 and R 8 are each independently a group represented by Formula 2;
R 1 and R 10 are each independently a group represented by Formula 2;
R 1 and R 8 are each independently a group represented by Formula 2;
R 1 and R 3 are each independently a group represented by Formula 2; or
R 8 and R 10 are each independently a group represented by Formula 2.

2. The amine-based compound of cl

Assignees

• Samsung Display Co Ltd

Inventors

• Jun Mi-Eun
• Han Sang-Hyun
• Kim Young-Kook
• Hwang Seok-Hwan
• Kho Sam-Il

Classifications

• C07C211/58

  Naphthylamines; N-substituted derivatives thereof · CPC title

• C07F7/081

  comprising at least one atom selected from the elements N, O, halogen, S, Se or Te · CPC title

• C07C2603/52

  containing five condensed rings · CPC title

• C07C2603/26

  Phenanthrenes; Hydrogenated phenanthrenes · CPC title

• C09B57/001

  Pyrene dyes · CPC title