Organic electroluminescent device comprising a redox-doped electron transport layer and an auxiliary electron transport layer

Patent metadata

Field	Value
Publication number	US-11532801-B2
Application number	US-201715784389-A
Country	US
Kind code	B2
Filing date	Oct 16, 2017
Priority date	Oct 24, 2016
Publication date	Dec 20, 2022
Grant date	Dec 20, 2022

Abstract

The present invention relates to an organic electroluminescent device, particularly to an organic light emitting diode (OLED) including an ETL stack of at least two electron transport layers, wherein the first electron transport layer comprises a first electron transport matrix compound and the second electron transport layer comprises second electron transport matrix compound and a redox n-dopant, and a device comprising the OLED.

First claim

The invention claimed is:

1. An organic electroluminescent device comprising an anode, a cathode, an emission layer arranged between the anode and the cathode, a first electron transport layer comprising a first electron transport matrix, a second electron transport layer comprising a second electron transport matrix and a redox n-dopant, wherein the first electron transport layer and the second electron transport layer are arranged between the emission layer and the cathode, wherein the first electron transport layer is arranged closer to the emission layer than the second electron transport layer and the second electron transport layer is arranged closer to the cathode than the first electron transport layer; wherein at least the first electron transport matrix comprises a matrix compound according to Chemical Formula I:

wherein
A 1 , A 2 , A 3 and A 4 is independently selected from single bond, an unsubstituted or substituted C 6 to C 30 arylene and an unsubstituted or substituted C 1 to C 30 heteroarylene;
A 5 is selected from an unsubstituted or substituted C 6 to C 40 aryl group and/or from an unsubstituted or substituted C 2 to C 40 heteroaryl group;
R 1 to R 5 are independently a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group;
a to e are independently an integer of 0 or 1 and 4≤a+b+c+d+e≤5; and
wherein in the substituted group, at least one hydrogen is replaced by
(i) deuterium,
(ii) a halogen,
(iii) a C 2 to C 60 tertiary amino group, wherein the nitrogen atom of the tertiary amino group is substituted with two independently selected C 1 to C 30 hydrocarbyl groups or the nitrogen atom of the C 2 to C 60 tertiary amino group forms a C 1 to C 30 heterocyclic group,
(iv) a C 2 to C 60 phosphine oxide group, wherein the phosphorus atom of the phosphine oxide group is substituted with two C 1 to C 30 groups independently selected from hydrocarbyl, halogenated hydrocarbyl and hydrocarbyloxy or the phosphorus atom of the phosphine oxide group forms a C 1 to C 30 heterocyclic group,
(v) a C 1 to C 22 silyl group,
(vi) a C 1 to C 30 alkyl group,
(vii) a C 1 to C 10 alkylsilyl group,
(viii) a C 6 to C 22 arylsilyl group,
(ix) a C 3 to C 30 cycloalkyl group,
(x) a C 2 to C 30 heterocycloalkyl group,
(xi) a C 6 to C 30 aryl group,
(xii) a C 2 to C 30 heteroaryl group,
(xiii) a C 1 to C 20 alkoxy group,
(xiv) a C 1 to C 30 perfluoro-hydrocarbyl group,
(xv) a C 1 to C 10 trifluoroalkyl group, or
(xvi) a cyano group, and

the redox dopant is
a) an elemental electropositive metal selected from an alkali metal, an alkaline earth metal, a rare earth metal, a transition metal, or a combination thereof, wherein the transition metal is selected from the group consisting of Ti, V, Cr, and Mn; and/or
b) an electrically neutral metal complex having redox potential which has a value which is more negative than −1.7 V, if measured by cyclic voltammetry against ferrocene/ferrocenium reference redox couple; and/or
c) an electrically neutral organic radical having redox potential which has a value which is more negative than −1.7 V, if measured by cyclic voltammetry against ferrocene/ferrocenium reference redox couple.

2. The organic electroluminescent device according to claim 1 , wherein the matrix compound (I) is a compound according to Chemical Formula (Ia)

wherein, in Chemical Formula Ia,
Ar 1 is selected from C 6 to C 12 arylene and C 1 to C 11 heteroarylene;
R 1 to R 5 are independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group;
a to e are independently an integer of 0 or 1 and 4≤a+b+c+d+e≤5;
L is a single bond, a substituted or unsubstituted C 6 to C 30 arylene group, or a substituted or unsubstituted C 2 to C 30 heteroarylene group;
ET is a unsubstituted C 6 to C 40 aryl or a unsubstituted C 5 to C 40 heteroaryl group, or a substituted C 6 to C 40 aryl or a substituted C 5 to C 40 heteroaryl group; and
wherein in the substituted group, at least one hydrogen is replaced by
(i) deuterium,
(ii) a halogen,
(iii) a C 2 to C 60 tertiary amino group, wherein the nitrogen atom of the C 2 to C 60 tertiary amino group is substituted with two independently selected C 1 to C 30 hydrocarbyl groups or forms a C 1 to C 30 heterocyclic group,
(iv) a C 2 to C 60 phosphine oxide group, wherein the phosphorus atom of the phosphine oxide group is substituted with two C 1 to C 30 groups independently selected from hydrocarbyl, halogenated hydrocarbyl and hydrocarbyloxy or the phosphorus atom of the phosphine oxide group forms a C 1 to C 30 heterocyclic group,
(v) a C 1 to C 22 silyl group,
(vi) a C 1 to C 30 alkyl group,
(vii) a C 1 to C 10 alkylsilyl group,
(viii) a C 6 to C 22 arylsilyl group,
(ix) a C 3 to C 30 cycloalkyl group,
(x) a C 2 to C 30 heterocycloalkyl group,
(xi) a C 6 to C 30 aryl group,
(xii) a C 2 to C 30 heteroaryl group,
(xiii) a C 1 to C 20 alkoxy group,
(xiv) a C 1 to C 30 perfluoro-hydrocarbyl group,
(xv) a C 1 to C 10 trifluoroalkyl group, or
(xvi) a cyano group.

3. The organic electroluminescent device according to claim 1 , wherein the matrix compound (I) is a compound according to Chemical Formula (Ib)

wherein in Chemical Formula Ib:
X 1 to X 11 are independently, N, C, or CR a ;
R a is independently, hydrogen, deuterium, a C 1 to C 30 alkyl group, a C 3 to C 30 cycloalkyl group, a C 6 to C 30 aryl group, a C 6 to C 30 diarylamine group, a C 1 to C 30 alkoxy group, a C 3 to C 21 silyl group, a C 3 to C 21 silyloxy group, a C 1 to C 30 alkylthiol group, a C 6 to C 30 arylthiol group, a halogen, a C 1 to C 30 halogenated hydrocarbyl group, a cyano group;
R 1 to R 5 are independently a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 2 to C 30 heteroaryl group;
a to e are independently an integer of 0 or 1 and 4≤a+b+c+d+e≤5;
L is a single bond, a substituted or unsubstituted C 6 to C 30 arylene group, a substituted or unsubstituted C 2 to C 30 heteroarylene group;
ET is a unsubstituted C 6 to C 40 aryl or a unsubstituted C 2 to C 40 heteroaryl group, or a substituted C 6 to C 40 aryl or a substituted C 2 to C 40 heteroaryl group; and
wherein in the substituted group, at least one hydrogen is replaced by
(i) deuterium,
(ii) a halogen,
(iii) a C 1 to C 60 tertiary amino group, wherein the nitrogen atom of the C 2 to C 60 tertiary amino group is substituted with two independently selected C 1 to C 30 hydrocarbyl groups or forms a C 1 to C 30 heterocyclic group,
(iv) a C 2 to C 60 phosphine oxide group, wherein the phosphorus atom of the phosphine oxide group is substituted with two C 1 to C 30 groups independently selected from hydrocarbyl, halogenated hydrocarbyl and hydrocarbyloxy or the phosphorus atom of the phosphine oxide group forms a C 1 to C 30 heterocyclic group,
(v) a C 1 to C 22 silyl group,
(vi) a C 1 to C 30 alkyl group,
(vii) a C 1 to C 10 alkylsilyl group,
(viii) a C 6 to C 22 arylsilyl group,
(ix) a C 3 to C 30 cycloalkyl group,
(x) a C 2 to C 30 heterocycloalkyl group,
(xi) a C 6 to C 30 aryl group,
(xii) a C 2 to C 30 heteroaryl group,
(xiii) a C 1 to C 20 alkoxy group,
(xi

Assignees

• Novaled Gmbh
• Samsung Sdi Co Ltd

Inventors

• Pavicic Domagoj
• Ganier Jerome
• Jankus Vygintas
• Kim Hyungsun
• Kim Byungku
• Kim Youngkwon
• Kim Younhwan
• Kim Hun
• Yu Eun Sun
• Jung Sung-Hyun

Classifications

• C07D239/70

  condensed with carbocyclic rings or ring systems · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title

• C07D251/24

  to three ring carbon atoms · CPC title

• C07D221/18 Primary

  Ring systems of four or more rings · CPC title

• H01L51/0071

  Electricity · mapped topic