US 11,968,887 B2Granted

Organic electroluminescence device and diamine compound for organic electroluminescence device

AssigneeSamsung Display Co., Ltd.

InventorTakao Sakuma

Life of this patent

Estimating the term…

Abstract

An organic electroluminescence device of an embodiment includes a first electrode, a hole transport region disposed on the first electrode, an emission layer disposed on the hole transport region, an electron transport region disposed on the emission layer, and a second electrode disposed on the electron transport region, wherein the hole transport region includes a diamine compound represented by Formula 1, thereby showing high emission efficiency:

Claims24

Dependent claims

An organic electroluminescence device, comprising:

a first electrode;
a hole transport region on the first electrode;
an emission layer on the hole transport region;
an electron transport region on the emission layer;
and
a second electrode on the electron transport region,
wherein the hole transport region comprises a diamine compound represented by Formula 1:
wherein in Formula 1,
Ar1 to Ar4 are each independently a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,
L1 is a direct linkage or a substituted or unsubstituted phenylene group,
L2 is a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms for forming a ring,
R1 and R2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,
x is an integer of 0 to 4,
y is an integer of 0 to 2, and
m and n are each independently an integer of 0 to 4, where m+n is not 0, and L1 and L2 are not both a direct linkage, and
wherein
i) when L2 is a naphthylene group,
the naphthylene group is represented by
where * represents a bindinq site to a neighboring atom, and
ii) when m is 1, n is 1, and L1 and L2 are each an unsubstituted phenylene group represented by
where * represents a bindinq site to a neighboring atom,
R1 and R2 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 5 carbon atoms, an unsubstituted phenyl group, or a substituted or unsubstituted carbazole group.

19 more elements

A diamine compound represented by Formula 1:

wherein in Formula 1,
Ar1 to Ar4 are each independently a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,
L1 is a direct linkage or a substituted or unsubstituted phenylene group,
L2 is a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms for forming a ring,
R1 and R2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,
x is an integer of 0 to 4,
y is an integer of 0 to 2, and
m and n are each independently an integer of 0 to 4, where m+n is not 0, and L1 and L2 are not both a direct linkage, and
wherein
i) when L2 is a naphthylene group,
the naphthylene group is represented by
where * represents a bindinq site to a neighboring atom, and
ii) when m is 1, n is 1, and L1 and L2 are each an unsubstituted phenylene group represented by
where * represents a bindinq site to a neighboring atom,
R1 and R2 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 5 carbon atoms, an unsubstituted phenyl group, or a substituted or unsubstituted carbazole group.

12 more elements

A diamine compound represented by Formula 1:

wherein the diamine compound represented by Formula 1 is at least one selected among compounds represented in Compound Group 1:
[Compound Group 1]
m
n
L1
L2
Ar1
A1-1
1
0
—
A1-2
1
0
—
A1-3
1
0
—
A1-4
1
0
—
A1-5
1
0
—
A1-6
1
0
—
A1-7
1
0
—
A1-8
1
0
—
A1-9
1
0
—
A1-10
1
0
—
A1-11
1
0
—
A1-12
1
0
—
A1-13
1
0
—
A1-14
1
0
—
A1-15
1
0
—
A1-16
1
0
—
A1-17
1
0
—
A1-18
1
0
—
A1-19
1
0
—
A1-20
1
0
—
A1-21
1
0
—
A1-22
1
0
—
A1-23
1
0
—
A1-24
1
0
—
A1-25
1
0
—
A1-26
1
0
—
A1-27
1
0
—
A1-28
1
0
—
A1-29
1
0
—
A1-30
1
0
—
A1-31
1
0
—
A1-32
1
0
—
A1-33
1
0
—
B1-1
1
0
—
B1-2
1
0
—
B1-3
1
0
—
B1-4
1
0
—
B1-5
1
0
—
B1-6
1
0
—
B1-7
1
0
—
B1-8
1
0
—
B1-9
1
0
—
B1-10
1
0
—
B1-11
1
0
—
B1-12
1
0
—
B1-13
1
0
—
B1-14
1
0
—
B1-15
1
0
—
B1-16
1
0
—
B1-17
1
0
—
B1-18
1
0
—
B1-19
1
0
—
B1-20
1
0
—
B1-21
1
0
—
B1-22
1
0
—
B1-23
1
0
—
B1-24
1
0
—
B1-25
1
0
—
B1-26
1
0
—
B1-27
1
0
—
B1-28
1
0
—
B1-29
1
0
—
B1-30
1
0
—
C1-1
1
0
—
C1-2
1
0
—
C1-3
1
0
—
C1-4
1
0
—
C1-5
1
0
—
C1-6
1
0
—
C1-7
1
0
—
C1-8
1
0
—
C1-9
1
0
—
C1-10
1
0
—
C1-11
1
0
—
C1-12
1
0
—
C1-13
1
0
—
C1-14
1
0
—
C1-15
1
0
—
C1-16
1
0
—
C1-17
1
0
—
C1-18
1
0
—
C1-19
1
0
—
C1-20
1
0
—
C1-21
1
0
—
C1-22
1
0
—
C1-23
1
0
—
C1-24
1
0
—
C1-25
1
0
—
C1-26
1
0
—
C1-27
1
0
—
C1-28
1
0
—
C1-29
1
0
—
C1-30
1
0
—
D1-1
1
0
—
D1-2
1
0
—
D1-3
1
0
—
D1-4
1
0
—
D1-5
1
0
—
D1-6
1
0
—
D1-7
1
0
—
D1-8
1
0
—
D1-9
1
0
—
D1-10
1
0
—
D1-11
1
0
—
D1-12
1
0
—
D1-13
1
0
—
D1-14
1
0
—
D1-15
1
0
—
D1-16
1
0
—
D1-17
1
0
—
D1-18
1
0
—
D1-19
1
0
—
D1-20
1
0
—
D1-21
1
0
—
D1-22
1
0
—
D1-23
1
0
—
D1-24
1
0
—
D1-25
1
0
—
D1-26
1
0
—
D1-27
1
0
—
D1-28
1
0
—
D1-29
1
0
—
D1-30
1
0
—
E1-1
1
0
—
E1-2
1
0
—
Ar2
Ar3
Ar4
A1-1
A1-2
A1-3
A1-4
A1-5
A1-6
A1-7
A1-8
A1-9
A1-10
A1-11
A1-12
A1-13
A1-14
A1-15
A1-16
A1-17
A1-18
A1-19
A1-20
A1-21
A1-22
A1-23
A1-24
A1-25
A1-26
A1-27
A1-28
A1-29
A1-30
A1-31
A1-32
A1-33
B1-1
B1-2
B1-3
B1-4
B1-5
B1-6
B1-7
B1-8
B1-9
B1-10
B1-11
B1-12
B1-13
B1-14
B1-15
B1-16
B1-17
B1-18
B1-19
B1-20
B1-21
B1-22
B1-23
B1-24
B1-25
B1-26
B1-27
B1-28
B1-29
B1-30
C1-1
C1-2
C1-3
C1-4
C1-5
C1-6
C1-7
C1-8
C1-9
C1-10
C1-11
C1-12
C1-13
C1-14
C1-15
C1-16
C1-17
C1-18
C1-19
C1-20
C1-21
C1-22
C1-23
C1-24
C1-25
C1-26
C1-27
C1-28
C1-29
C1-30
D1-1
D1-2
D1-3
D1-4
D1-5
D1-6
D1-7
D1-8
D1-9
D1-10
D1-11
D1-12
D1-13
D1-14
D1-15
D1-16
D1-17
D1-18
D1-19
D1-20
D1-21
D1-22
D1-23
D1-24
D1-25
D1-26
D1-27
D1-28
D1-29
D1-30
E1-1
E1-2

632 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/099,550Filed 16 Nov 2020
Priority: KR 10-2019-015480627 Nov 2019
Published: US 2022/0344589 A127 Oct 2022
Granted: 23 Apr 2024
Term ends: Not estimatedThe source records don’t support an estimate.

Classification22 codes

C07D 233/52
Nitrogen atoms not forming part of a nitro radical: with hetero atoms directly attached to said nitrogen atoms
C07C 211/54
Having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton: having amino groups bound to two or three…
C07C 211/55
Having amino groups bound to two or three six-membered aromatic rings: diphenylamines
C07C 211/58
Having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton:…

Family

US 2022/0344589 A1Pre-grant publication · published 27 Oct 2022
US 11,930,702 B2Related patent
US 11,968,887 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

An organic electroluminescence device, comprising:

a first electrode;
a hole transport region on the first electrode;
an emission layer on the hole transport region;
an electron transport region on the emission layer;
and
a second electrode on the electron transport region,
wherein the hole transport region comprises a diamine compound represented by Formula 1:
wherein in Formula 1,
Ar1 to Ar4 are each independently a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,
L1 is a direct linkage or a substituted or unsubstituted phenylene group,
L2 is a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms for forming a ring,
R1 and R2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,
x is an integer of 0 to 4,
y is an integer of 0 to 2, and
m and n are each independently an integer of 0 to 4, where m+n is not 0, and L1 and L2 are not both a direct linkage, and
wherein
i) when L2 is a naphthylene group,
the naphthylene group is represented by
where * represents a bindinq site to a neighboring atom, and
ii) when m is 1, n is 1, and L1 and L2 are each an unsubstituted phenylene group represented by
where * represents a bindinq site to a neighboring atom,
R1 and R2 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 5 carbon atoms, an unsubstituted phenyl group, or a substituted or unsubstituted carbazole group.

19 more elements

Facts

Application

17/099,550Filed 16 Nov 2020

Priority

KR 10-2019-015480627 Nov 2019

Published

US 2022/0344589 A127 Oct 2022

Granted

23 Apr 2024

Term ends

Not estimatedThe source records don’t support an estimate.

Classification22 codes

C07D 233/52
Nitrogen atoms not forming part of a nitro radical: with hetero atoms directly attached to said nitrogen atoms
C07C 211/54
Having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton: having amino groups bound to two or three…
C07C 211/55
Having amino groups bound to two or three six-membered aromatic rings: diphenylamines
C07C 211/58
Having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton:…