Organometallic compound, light-emitting device including the same, and electronic apparatus

Patent metadata

Field	Value
Publication number	US-12101996-B2
Application number	US-202117384623-A
Country	US
Kind code	B2
Filing date	Jul 23, 2021
Priority date	Jul 31, 2020
Publication date	Sep 24, 2024
Grant date	Sep 24, 2024

Abstract

An organometallic compound represented by Formula 1, a light-emitting device including the same, and an electronic apparatus including the light-emitting device are disclosed. In Formula 1, the substituents are as described in more detail in the specification.

First claim

What is claimed is:

1. A light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode; and
an interlayer between the first electrode and the second electrode and comprising an emission layer,
wherein the interlayer comprises at least one organometallic compound represented by Formula 1:

wherein, in Formula 1,
M 1 is selected from the group consisting of platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),
Y 1 to Y 3 are each independently selected from the group consisting of a carbon atom (C) and a nitrogen atom (N),
T 1 to T 4 are each independently a chemical bond, O, S, B(R′), N(R′), P(R′), C(R′)(R″), Si(R′)(R″), Ge(R′)(R″), or C(═O),
when T 1 is a chemical bond, Y 1 and M 1 are directly bonded to each other,
when T 2 is a chemical bond, Y 2 and M 1 are directly bonded to each other,
when T 3 is a chemical bond, Y 3 and M 1 are directly bonded to each other,
when T 4 is a chemical bond, C in ring A 4 is directly bonded to M 1 ,
two bonds selected from the group consisting of a bond between M 1 and Y 1 or T 1 , a bond between M 1 and Y 2 or T 2 , a bond between M 1 and Y 3 or T 3 , and a bond between M 1 and C in ring A 4 or T 4 are each a coordinate bond, and the remaining two bonds are each a covalent bond,
ring A 1 to ring A 3 , ring A 11 and ring A 12 are each independently selected from the group consisting of a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group,
L 1 to L 3 are each independently selected from the group consisting of a single bond, a double bond, *—N(R 4 )—*′, *—B(R 4 )—*′, *—P(R 4 )—*′, *—C(R 4 )(R 5 )—*′, *—Si(R 4 )(R 5 )—*′, *—Ge(R 4 )(R 5 )—*′, *—S—*′, *—Se*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(R 4 )═*′, *═C(R 4 )—*′, *—C(R 4 )═C(R 5 )—*′, *—C(═S)—*′ and *—C≡C—*′,
a1 to a3 are each independently an integer from 0 to 3,
when a1 is 0, ring A 1 and ring A 2 are not linked to each other,
when a2 is 0, ring A 2 and ring A 3 are not linked to each other,
when a3 is 0, ring A 3 and ring A 4 are not linked to each other,
R′, R″, R 1 to R 5 , R 11 and R 12 are each independently selected from the group consisting of hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), and —P(═S)(Q 1 )(Q 2 ),
b1 to b3, b11 and b12 are each independently an integer from 1 to 20,
two or more neighboring groups from among R 1 to R 5 , R 11 and R 12 are optionally bonded to form a C 5 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , * and *′ each indicate a binding site to a neighboring atom, and
R 10a is:
deuterium (—D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio 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 ), —P(═O)(Q 11 )(Q 12 ), or any combination thereof;
a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, or a C 6 -C 60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or any combination thereof; or
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ), and wherein Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C 1 -C 60 alkyl group; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy group; or a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

2. The light-emitting device of claim 1 , wherein
the first electrode is an anode,
the second electrode is a cathode,
the interlayer further comprises a hole transport region between the first electrode and the emission layer and an electron 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 buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

3. The light-emitting device of claim 1 , further comprising a capping layer on the second electrode,
wherein the capping layer comprises a material having a refractive index of 1.6 or more at a wavelength of 589 nm.

4. The light-emitting device of claim 1 , wherein the emission layer comprises the at least one organometallic compound.

5. The light-emitting device of claim 4 , wherein the emission layer further comprises a host, and an amount of the at least one organometallic compound is from 0.01 parts by weight to 49.99 parts in amount by weight based on 100 parts by weight of the emission layer.

6. The light-emitting device of claim 4 , wherein the emission layer is configured to emit green light having a maximum luminescence wavelength of 500 nm to 570 nm.

7. The light-emitting device of claim 2 , wherein the electron transport region comprises a phosphine oxide-containing compound.

8. An electronic apparatus comprising the light-emitting device of claim 1 .

9. The electronic apparatus of claim 8 , further comprising a thin-film transistor,
wherein the thin-film transistor comprises a source electrode and a drain electrode, and
the first electrode of the light-emitting device is electrically connected to the source electrode or the drain electrode of the thin-film transistor.

10. The electronic apparatus of claim 8 , further comprising a color filter, a color conversio

Assignees

• Samsung Display Co Ltd

Inventors

• Lee Eunyoung
• Ko Soobyung
• Kim Haejin
• Shin Sujin
• Ahn Eunsoo
• HAN Junghoon

Classifications

• H10K85/346 Primary

  comprising platinum · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K59/123

  Connection of the pixel electrodes to the thin film transistors [TFT] · CPC title

• H10K50/858

  comprising refractive means, e.g. lenses · CPC title