Azide-based compound, organic light-emitting device including the azide-based compound, and method of manufacturing the organic light-emitting device

Patent metadata

Field	Value
Publication number	US-12178114-B2
Application number	US-201916599212-A
Country	US
Kind code	B2
Filing date	Oct 11, 2019
Priority date	Dec 21, 2018
Publication date	Dec 24, 2024
Grant date	Dec 24, 2024

Abstract

Provided are an azide-based compound, an organic light-emitting device including the azide-based compound, and a method of manufacturing the organic light-emitting device.

First claim

What is claimed is:

1. An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode;
an organic layer disposed between the first electrode and the second electrode and comprising an emission layer; and
an azide-based compound represented by Formula 1:
wherein the organic layer further comprises a hole transport region between the first electrode and the emission layer,
wherein the hole transport region comprises the at least one of the azide-based compound and a polymer having a molecular weight of about 5,000 g/mol or greater:

wherein, in Formula 1,
each of L 1 , L 2 , and L 3 and L 11 to L 12 is independently a single bond or a substituted or unsubstituted C 1 -C 10 alkylene group,
each of a1, a2, and a3 and a11 to a12 is independently an integer from 1 to 5, wherein, when a1 is two or more, two or more L 1 (s) are identical to or different from each other, when a2 is two or more, two or more L 2 (s) are identical to or different from each other, when a3 is two or more, two or more L 3 (s) are identical to or different from each other, when a11 is two or more, two or more L 11 (s) are identical to or different from each other, and when a12 is two or more, two or more L 12 (s) are identical to or different from each other,
each of b1 and b2 is independently an integer of 1 or 2,
b3 is an integer of 0 or 1,
when b3 is 0, *-((L 3 ) a3 -N 3 ) b3 is hydrogen,
when b1 is two or more, two or more *-((L 1 ) a1 -N 3 )(s) are identical to or different from each other, and when b2 is two or more, two or more *-((L 2 ) a2 -N 3 )(s) are identical to or different from each other,
* indicates a binding site to a neighboring atom, and
at least one substituent of the substituted C 1 -C 10 alkylene group is selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 10 alkyl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, and a C 1 -C 10 alkoxy group.

2. The organic light-emitting device of claim 1 , wherein
the first electrode is an anode,
the second electrode is a cathode,
the organic layer comprises at least one of the azide-based compound represented by Formula 1,
the organic layer further comprises a hole transport region between the emission layer and the second electrode,
the hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and
the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

3. The organic light-emitting device of claim 1 , wherein
the emission layer comprises a host material and a dopant material, and
the dopant material comprises a phosphorescent dopant or a fluorescent dopant.

4. The organic light-emitting device of claim 1 , wherein each of L 1 , L 2 , and L 3 is independently a single bond.

5. The organic light-emitting device of claim 1 , wherein
each of L 11 and L 12 is independently selected from:
a single bond, a methylene group, an ethylene group, a propylene group, a butylene group, and a pentylene group; and
a methylene group, an ethylene group, a propylene group, a butylene group, and a pentylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, and a C 1 -C 10 alkyl group.

6. The organic light-emitting device of claim 1 , wherein
*-(L 11 ) a11 -*′ and *-(L 12 ) a12 -*′ are identical to each other.

7. The organic light-emitting device of claim 1 , wherein
the azide-based compound has a molecular weight of about 100 g/mol to about 2,000 g/mol.

8. The organic light-emitting device of claim 1 , wherein
a sum of b1, b2, and b3 is 2, 3, or 4.

9. The organic light-emitting device of claim 6 , wherein
the azide-based compound is represented by Formula 1-1:

wherein, in Formula 1-1,
each of b1 and b2 is independently an integer of 1 or 2,
b3 is an integer of 0 or 1,
when b3 is 0, *-((L 3 ) a3 -N 3 ) b3 is hydrogen,
when b1 is two or more, two or more *-((L 1 ) a1 -N 3 )(s) are identical to or different from each other, and when b2 is two or more, two or more *-((L 2 ) a2 -N 3 )(s) are identical to or different from each other,
* indicates a binding site to a neighboring atom,
each of Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , and Z 8 is independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 10 alkyl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, and a C 1 -C 10 alkoxy group.

10. The organic light-emitting device of claim 1 , wherein
the azide-based compound is selected from Compounds 1, 2, and 3:

11. A composition comprising:
the azide-based compound of claim 1 ;
a polymeric compound represented by Formula 2; and
a solvent:

wherein, in Formula 2,
each of Ar 1 , Ar 2 , and Ar 3 is independently a substituted or unsubstituted C 3 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
to each of c1 and c2 is independently an integer from 1 to 3,
n is an integer from 70 to 400,
at least one substituent of the substituted C 3 -C 60 carbocyclic group and the substituted C 1 -C 60 heterocyclic group is selected from:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), and —P(═O)(Q 11 )(Q 12 );
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group;
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 h

Assignees

• Samsung Display Co Ltd

Inventors

• Park Junwoo
• Kim Dukki
• Kim Jaeyun
• Shin Dongwoo
• Ha Jaekook

Classifications

• H10K71/40

  Thermal treatment, e.g. annealing in the presence of a solvent vapour · CPC title

• H10K71/12

  using liquid deposition, e.g. spin coating · CPC title

• H10K50/16

  Electron transporting layers · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• H10K85/141

  comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE · CPC title