Organic optoelectric device and display device

Patent metadata

Field	Value
Publication number	US-10074810-B2
Application number	US-201514864942-A
Country	US
Kind code	B2
Filing date	Sep 25, 2015
Priority date	Oct 31, 2014
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

Abstract

An organic optoelectric device including an anode and a cathode facing each other, an emission layer between the anode and the cathode, a hole transport layer between the anode and the emission layer, a hole transport auxiliary layer between the hole transport layer and the emission layer, an electron transport layer between the cathode and the emission layer, and an electron transport auxiliary layer between the electron transport layer and the emission layer, wherein the electron transport auxiliary layer includes a first compound represented by the following Chemical Formula 1, and the hole transport auxiliary layer includes a second compound represented by the following Chemical Formula 2:

First claim

What is claimed is:

1. An organic optoelectric device, comprising:
an anode and a cathode facing each other,
an emission layer between the anode and the cathode,
a hole transport layer between the anode and the emission layer,
a hole transport auxiliary layer between the hole transport layer and the emission layer,
an electron transport layer between the cathode and the emission layer, and
an electron transport auxiliary layer between the electron transport layer and the emission layer,
wherein the electron transport auxiliary layer includes a first compound represented by the following Chemical Formula 1, and
the hole transport auxiliary layer includes a second compound represented by the following Chemical Formula 2:

wherein, in Chemical Formula 1,
each Z is independently N or CR a , at least one Z being N,
R 1 to R 10 and R a are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof,
L 1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group,
n1 to n3 are each independently 0 or 1,
n 1+ n 2+ n 3≥1,

wherein, in Chemical Formula 2,
L 2 is a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C6 to C30 heteroarylene group,
n4 is an integer of 1 to 5,
R 11 to R 22 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, or a combination thereof,
R 11 to R 20 are separate or are fused with an adjacent group to form a ring,
wherein “substituted” of Chemical Formulae 1 and 2 refers to that at least one hydrogen is replaced by deuterium, a halogen, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group.

2. The organic optoelectric device as claimed in claim 1 , wherein the first compound is represented by the following Chemical Formula 1-I or Chemical Formula 1-II:

wherein, in Chemical Formulae 1-I and 1-II,
each Z is independently N or CR a , at least one Z being N,
R 1 to R 10 and R a are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof,
L 1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group,
n1 to n3 are each independently 0 or 1, and
n 1+ n 2+ n 3≥1,

wherein “substituted” refers to that at least one hydrogen is replaced by deuterium, a halogen, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group.

3. The organic optoelectric device as claimed in claim 1 , wherein the first compound is one of the following Compounds A-1 to A-125:

4. The organic optoelectric device as claimed in claim 1 , wherein the electron transport auxiliary layer further includes a third compound represented by the following Chemical Formula 3:

wherein, in Chemical Formula 3,
Y 1 and Y 2 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
Ar 1a and Ar 1b are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and
R 23 to R 28 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, or a combination thereof,
wherein “substituted” refers to that at least one hydrogen is replaced by deuterium, a halogen, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, or a cyano group.

5. The organic optoelectric device as claimed in claim 4 , wherein the third compound is represented by one of the following Chemical Formulae 3-IX to 3-XI:

wherein, in Chemical Formulae 3-IX to 3-XI,
Y 1 and Y 2 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
R 23 to R 28 are each independently hydrogen, deuterium, a substituted or unsubstitute

Assignees

• Samsung Sdi Co Ltd

Inventors

• Lui Jin-Hyun
• Park Jae-Han
• Jo Young-Kyoung
• Kim Chang-Woo
• Min Soo-Hyun
• Yu Eun-Sun
• Lee Han-Ill
• Jung Sung-Hyun
• Jung Ho-Kuk

Classifications

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• Y10S428/917

  Electroluminescent · CPC title

• C09K2211/1074

  containing more than three nitrogen atoms as heteroatoms · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• Y02E10/549

  Organic PV cells · CPC title