Phosphine oxide-based compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-9627627-B2
Application number	US-201314014732-A
Country	US
Kind code	B2
Filing date	Aug 30, 2013
Priority date	Sep 14, 2012
Publication date	Apr 18, 2017
Grant date	Apr 18, 2017

Abstract

A phosphine oxide-based compound represented by Formula 1, and an organic light-emitting device including the phosphine oxide-based compound.

wherein Ar 1 through Ar 3 , and a, b, and c are defined as in the specification.

First claim

What is claimed is:

1. A phosphine oxide-based compound represented by Formula 1 below:

wherein Ar 1 to Ar 3 are each independently deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, or an N-containing electron withdrawing group;
a, b and c are each independently an integer from 0 to 5;
the sum of a, b, and c must be greater than or equal to 1; and
at least one of a number of Ar 1 s, b number of Ar 2 s, and c number of Ar 3 s is an N-containing electron withdrawing group,
wherein the N-containing electron withdrawing group is selected from among:
a substituted or unsubstituted pyrrolyl group,
a substituted or unsubstituted pyrazolyl group,
an unsubstituted imidazolyl group,
a substituted or unsubstituted imidazolinyl group,
a substituted or unsubstituted imidazopyridinyl group,
a substituted or unsubstituted imidazopyrimidinyl group,
a substituted or unsubstituted pyrazinyl group,
an unsubstituted pyrimidinyl group,
a substituted benzoimidazolyl group,
a substituted or unsubstituted indolyl group,
a substituted or unsubstituted purinyl group,
a substituted or unsubstituted quinolinyl group,
a substituted or unsubstituted isoquinolyl group,
a substituted or unsubstituted phthalazinyl group,
a substituted or unsubstituted indolizinyl group,
a substituted or unsubstituted naphthyridinyl group,
a substituted or unsubstituted quinazolinyl group,
a substituted or unsubstituted cinnolinyl group,
a substituted or unsubstituted indazolyl group,
a substituted or unsubstituted isothiazolyl group,
a substituted or unsubstituted isoxazolyl group,
a substituted or unsubstituted triazinyl group,
a substituted or unsubstituted oxadiazolyl group,
a substituted or unsubstituted pyridazinyl group,
a substituted or unsubstituted triazolyl group,
a substituted or unsubstituted tetrazolyl group,
a substituted or unsubstituted benzothiazolyl group, and
a substituted or unsubstituted benzoxazolyl group.

2. The phosphine oxide-based compound of claim 1 , wherein the N-containing electron withdrawing group is selected from among:
an unsubstituted pyrimidinyl group,
a substituted or unsubstituted pyrazinyl group,
a substituted or unsubstituted triazinyl group,
a substituted or unsubstituted quinolinyl group,
a substituted or unsubstituted isoquinolinyl group,
a substituted benzoimidazolyl group,
a substituted or unsubstituted imidazopyridinyl group,
a substituted or unsubstituted imidazopyrimidinyl group,
a substituted or unsubstituted benzothiazolyl group, and
a substituted or unsubstituted benzoxazolyl group.

3. The phosphine oxide-based compound of claim 1 , wherein the N-containing electron withdrawing group is represented by one of Formulae 2C to 2L:

wherein Z 1 and Z 2 are each independently selected from deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group and a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group 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 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 3 -C 10 cycloalkenyl group and a C 6 -C 60 aryl group; a C 6 -C 60 aryl group substituted with at least one of —F, —CN, and a C 1 -C 10 alkyl group; and a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group and a C 2 -C 60 heteroaryl group;
c 1 is an integer from 0 to 4;
c 2 is an integer of 0 to 3;
c 3 is an integer from 0 to 2;
c 4 is an integer of 0 to 6;
c 5 is an integer from 0 to 5; and
T 1 is O or S.

4. The phosphine oxide-based compound of claim 3 , wherein the Z 1 and Z 2 are each independently deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxylic group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group, or a phenanthrenyl group.

5. The phosphine oxide-based compound of claim 2 , wherein the N-containing electron withdrawing group is represented by Formula 2I below:

wherein Z 1 is a phenyl group, a naphthyl group, an anthryl group, or a phenanthrenyl group, and Z 2 is independently selected from deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group and a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group 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 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 3 -C 10 cycloalkenyl group and a C 6 -C 60 aryl group; a C 6 -C 60 aryl group substituted with at least one of —F, —CN, and a C 1 -C 10 alkyl group; and a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group and a C 2 -C 60 heteroaryl group; and
c 1 is an integer from 0 to 4.

6. The phosphine oxide-based compound of claim 1 , wherein at least two of the a number of Ar 1 s, the b number of Ar 2 s, and the c number of Ar 3 s are N-containing electron withdrawing groups.

7. The phosphine oxide-based compound of claim 1 , wherein a, b, and c are all 1, and at least two of Ar 1 , Ar 2 , and Ar 3 are N-containing electron withdrawing groups.

8. The phosphine oxide-based compound of claim 1 , wherein the phosphine oxide-based compound is a compound represented by Formula 1A below:

wherein Ar 1 to Ar 3 are each independently deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a sub

Assignees

• Samsung Display Co Ltd
• Industry-Academic Coop Found Gyeongsang Nat Univ

Inventors

• Kim Mi-Kyung
• Lee Kwan-Hee
• Chu Chang-Woong
• Kim Yun-Hi
• Kwon Soon-Ki
• Yoo Seung-Jin

Classifications

• C07F15/0086

  Platinum compounds · CPC title

• C07F15/0026

  without a metal-carbon linkage · CPC title

• C07F15/0033

  Iridium compounds · CPC title

• C07F15/0093

  without a metal-carbon linkage · CPC title

• C07F9/6561

  containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings · CPC title