Organic Electroluminescent Device Comprising a Redox-Doped Electron Transport Layer and an Auxiliary Electron Transport Layer

Patent metadata

Field	Value
Publication number	US-2018114940-A1
Application number	US-201715784389-A
Country	US
Kind code	A1
Filing date	Oct 16, 2017
Priority date	Oct 24, 2016
Publication date	Apr 26, 2018
Grant date	—

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

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.

2 . The organic electroluminescent device according to claim 1 , wherein the redox n-dopant is selected from an elemental metal, an electrically neutral metal complex and/or an electrically neutral organic radical.

3 . The organic electroluminescent device according to claim 2 , wherein the electrically neutral metal complex and/or the electrically neutral organic radical has a 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.

4 . 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.

5 . 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,
(xiv) a C 1 to C 30 perfluoro-hydrocarbyl group,
(xv) a C 1 to C 10 trifluoroalkyl group, or
(xvi) a cyano group.

6 . The organic elect

Assignees

• Novaled Gmbh
• Samsung Sdi Co Ltd

Inventors

• Pavicic Domagoj
• Ganier Jerome
• Jankus Vygintas
• Kim Hyungsun
• Kim Byungku

Classifications

• C07D239/70

  condensed with carbocyclic rings or ring systems · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title

• H01L2251/554

  Electricity · mapped topic

• C07D221/18 Primary

  Ring systems of four or more rings · CPC title

• C07D251/24

  to three ring carbon atoms · CPC title