IP Library Granted Patent US 8,026,665
Granted Patent B2
US 8,026,665 · App. 11/913,683 · Granted Sep 27, 2011

Deuterated aryl amine compound, preparation method thereof, and organic light emitting diode using the same

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Quick Facts
Patent No.
US 8,026,665
App. No.
11/913,683
Granted
Sep 27, 2011
Kind
B2
Abstract

Disclosed are a novel deuterated aryl amine compound capable of enhancing thermal stability, hole transporting capability, luminescence efficiency, etc. of an organic light emitting diode at the time of being used as a hole-injecting layer, a preparation method thereof, and an organic light emitting diode using the same.

Claims (12)

1. A deuterated aryl amine compound consisting essentially of, the compound represented by Formula HIL-1 or Formula HIL-2:

2. An organic light emitting diode, comprising a hole injecting layer and a light emitting layer, said hole injecting layer consisting essentially of the deuterated aryl amine compound according to claim 1 .

3. A method for preparing the aryl amine compound of claim 1 , comprising:

(1) reacting a compound of Formula 6 with a compound of Formula 7a and/or 7b, followed by halogenating the resulting product, to obtain compounds represented by general formulae Ar 1 —Y and Ar 2 —Y;

(2) reacting any one compound shown in Formula 8 with a compound of Formula 9, to obtain a compound of Formula 5; and

(3) reacting the compound of Formula 5 with compounds represented by general formulae Ar 1 —Y and Ar 2 —Y, to obtain the compound of Formula 1:

wherein Ar 1 and Ar 2 are respectively a diphenylaminophenyl group represented by Formula 2 and are identical to or different from each other;

Ar 3 and Ar 4 are respectively a naphthyl group represented by Formula 3 and are identical to or different from each other;

R 1 to R 21 are respectively selected from the group consisting of hydrogen, deuterium, C 1 -C 30 alkyl group and a halogen atom, provided that at least one of R 1 to R 21 are deuterium atom;

X is selected from the species of structures shown in Formula 4 and may be unsubstituted or substituted with at least one deuterium atoms;

Y is a halogen atom selected from F, Cl, Br and I; and

Z is hydrogen or deuterium.

Assignments (4)
CHANGE OF NAME Recorded Jan 4, 2021
From: DOOSAN SOLUS CO., LTD.
To: SOLUS ADVANCED MATERIALS CO., LTD.
Reel/Frame 054887/0911 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 18, 2020
From: DOOSAN CORPORATION
To: DOOSAN SOLUS CO., LTD.
Reel/Frame 052970/0277 →
CHANGE OF ADDRESS Recorded Jun 18, 2020
From: DOOSAN CORPORATION
To: DOOSAN CORPORATION
Reel/Frame 052971/0480 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2007
From: KIM, KYOUNG-SOO; KIM, TAE-HYUNG; YOUN, KYU-MAN; SEO, HYEON-JIN; KO, MYUNG-SOO; LEE, SANG-HOON; RYU, DONG-WAN; KIM, YEONG-EUN
To: DOOSAN CORPORATION
Reel/Frame 020070/0768 →