Organic electroluminescent device

Patent metadata

Field	Value
Publication number	US-11917907-B2
Application number	US-202117532294-A
Country	US
Kind code	B2
Filing date	Nov 22, 2021
Priority date	Jul 22, 2014
Publication date	Feb 27, 2024
Grant date	Feb 27, 2024

Abstract

The present disclosure relates to an organic electroluminescent device. The organic electroluminescent device of the present disclosure shows high luminous efficiency and good lifespan by comprising a specific combination of the plural kinds of host compounds and a specific hole transport compound.

First claim

The invention claimed is:

1. An organic electroluminescent device comprising an anode, a cathode, and an organic layer between the anode and the cathode,
wherein the organic layer comprises one or more light-emitting layers and one or more hole transport layers; at least one of the one or more light-emitting layers comprises one or more dopant compounds and two or more host compounds; a first host compound of the two or more host compounds is represented by the following formula 1; a second host compound is represented by the following formula 2; and at least one of the one or more hole transport layers comprises the compound represented by the following formula 3:

wherein
A 1 and A 2 , each independently, represent a deuterium-substituted or unsubstituted (C6-C18)aryl;
L 1 represents a single bond or a substituted or unsubstituted (C6-C30)arylene;
X 1 to X 16 , each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl containing at least one hetero atom selected from B, N, O, S, Si, and P, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl;

wherein
Ma represents a substituted or unsubstituted nitrogen-containing 5- to 11-membered heteroaryl;
La represents a substituted or unsubstituted (C6-C30)arylene;
Xa to Xh, each independently, represent hydrogen, deuterium, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl containing at least one heteroatom selected from O and S, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur, with the proviso that at least one of Xa to Xh is not hydrogen;

wherein
A 4 and A 5 , each independently, represent a substituted or unsubstituted (C6-C30)aryl;
L 3 represents a single bond or a substituted or unsubstituted (C6-C30)arylene;
Z 1 to Z 9 , each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di-(C6-C30)arylamino provided that at least one of Z 1 to Z 9 is linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
n represents an integer of 0;
t represents an integer of 0, 1, or 2; and
the heteroaryl contains at least one hetero atom selected from B, N, O, S, Si, and P.

2. The organic electroluminescent device according to claim 1 , wherein in formula 1, A 1 and A 2 , each independently, represent a deuterium-substituted or unsubstituted (C6-C18)aryl wherein the (C6-C18)aryl is selected from the group consisting of a phenyl, a biphenyl, a terphenyl, a naphthyl, a fluorenyl, a benzofluorenyl, a phenanthrenyl, a anthracenyl, a indenyl, a triphenylenyl, a pyrenyl, a tetracenyl, a perylenyl, a chrysenyl, a phenylnaphthyl, a naphthylphenyl, and a fluoranthenyl.

3. The organic electroluminescent device according to claim 1 , wherein in formula 1, Li represents a single bond, or one selected from the following formulae 9 to 21

wherein
Xi to Xp, each independently, represent hydrogen, deuterium a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, or a substituted or unsubstituted 3- to 30-membered heteroaryl; and represents a bonding site.

4. The organic electroluminescent device according to claim 1 , wherein in formula 2, Ma represents a substituted or unsubstituted monocyclic ring-type heteroaryl selected from the group consisting of a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted tetrazinyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted tetrazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyrimidinyl, and a substituted or unsubstituted pyridazinyl, or a substituted or unsubstituted fused ring-type heteroaryl selected from the group consisting of a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted isoindolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted indazolyl, a substituted or unsubstituted benzothiadiazolyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted cinnolinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted naphthyridinyl, and a substituted or unsubstituted quinoxalinyl.

5. The organic electroluminescent device according to claim 1 , wherein in formula 2, La represents a single bond, or one selected from the following formulae 9 to 21

Wherein
Xi to Xp, each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, or a substituted or unsubstituted 3- to 30-membered heteroaryl; and sulfur; and represents a bonding site.

6. The organic electroluminescent device according to claim 1 , wherein in formula 2, Xa to Xh, each independently, represent hydrogen, a cyano, a (C6-C15)aryl unsubstituted or substituted with a tri(C6-C10)arylsilyl, or a 10- to 20-membered heteroaryl containing at least one heteroatom selected from O and S unsubstituted or substituted with a (C6-C12)aryl; or may be linked to an adjacent subs

Assignees

• Rohm & Haas Elect Materials Korea Ltd

Inventors

• Park Kyoung-Jin
• Lee Tae-Jin
• Shim Jae-Hoon
• Doh Yoo Jin
• Ahn Hee-Choon
• Kim Young-Kwang
• Moon Doo-Hyeon
• Yang Jeong-Eun
• Lee Su-Hyun
• Kim Chi-Sik
• Jun Ji-Song

Classifications

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H10K50/00 Primary

  Organic light-emitting devices (integrated devices or assemblies of multiple devices H10K59/00, H10K65/00; organic semiconductor lasers H01S5/36) · CPC title

• H10K85/633 Primary

  comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• C07D209/86

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• C07D405/14

  containing three or more hetero rings · CPC title