Composition and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-11495758-B2
Application number	US-202016912752-A
Country	US
Kind code	B2
Filing date	Jun 26, 2020
Priority date	Jul 1, 2019
Publication date	Nov 8, 2022
Grant date	Nov 8, 2022

Abstract

A composition including a platinum-containing organometallic compound, a first compound, a second compound, and a third compound, and an organic light-emitting device including the same wherein the composition does not comprise iridium,the Pt-containing organometallic compound, the first compound, the second compound, and the third compound are different from each other,the first compound comprises at least one electron transport moiety,the second compound and the third compound do not include a metal,each of an absolute value of a HOMO energy level of the second compound and an absolute value of a HOMO energy level of the third compound is 5.30 eV to 5.85 eV,the difference between the absolute value of the HOMO energy level of the second compound and the absolute value of the HOMO energy level of the third compound is 0.01 eV to 0.30 eV.

First claim

What is claimed is:

1. A composition comprising a platinum-containing organometallic compound, a first compound, a second compound, and a third compound,
wherein the composition does not comprise iridium,
the Pt-containing organometallic compound, the first compound, the second compound, and the third compound are different from each other,
the first compound comprises at least one electron transport moiety,
the second compound and the third compound do not include a metal,
each of an absolute value of a HOMO energy level of the second compound and an absolute value of a HOMO energy level of the third compound is 5.30 eV to 5.85 eV,
the difference between the absolute value of the HOMO energy level of the second compound and the absolute value of the HOMO energy level of the third compound is 0.01 eV to 0.30 eV, and
each of the HOMO energy level of the second compound and the HOMO energy level of the third compound is measured using a photoelectron spectrometer in air.

2. The composition of claim 1 , wherein
the Pt-containing organometallic compound comprises Pt and a tetradentate organic ligand, wherein the Pt and the tetradentate organic ligand form 3 or 4 cyclometallated rings.

3. The composition of claim 2 , wherein
the tetradentate organic ligand comprises a benzimidazole group and a pyridine group.

4. The composition of claim 1 , wherein
an absolute value of the HOMO energy level of the Pt-containing organometallic compound is 5.25 eV to 5.55 eV, and
the HOMO energy level of the Pt-containing organometallic compound is measured using a photoelectron spectrometer in air.

5. The composition of claim 1 , wherein
the electron transport moiety is a cyano group, a fluoro group, a π-electron-deficient nitrogen-containing cyclic group, a group represented by one of the following formulae, or any combination thereof:

wherein, in the formulae above, *, *′, and *″ each indicate a binding site to a neighboring atom.

6. The composition of claim 1 , wherein
at least one of the second compound and the third compound does not include an electron transport moiety.

7. The composition of claim 1 , wherein
at least one of the second compound and the third compound independently comprises:
i) a condensed ring in which one or more fifth rings and one or more sixth rings are condensed with each other,
ii) a group represented by

or
iii) any combination thereof,
the fifth ring is a cyclopentadiene group, a pyrrole group, a furan group, a thiophene group, or a silole group,
the sixth ring is a π-electron-rich C 3 -C 30 cyclic group, and
*, *′, and *″ each indicate a binding site to a neighboring atom.

8. The composition of claim 1 , wherein
the Pt-containing organometallic compound is an organometallic compound represented by Formula 1,
the first compound is a compound represented by Formula 2, or
the second compound and the third compound are each independently represented by one of Formulae 3-1 to 3-4:

wherein, M in Formula 1 is Pt,
Y 1 to Y 4 in Formula 1 are each independently a chemical bond, O, S, N(R a ), C(R a )(R b ), or Si(R a )(R b ),
X 1 to X 4 in Formula 1 are each independently C or N,
ring CY 1 to ring CY 4 in Formula 1 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
T 1 in Formula 1 is a single bond, a double bond, *—N(R 51 )—*′, *—B(R 51 )—*′, *—P(R 51 )—*′, *—C(R 51 )(R 52 )—*′, *—Si(R 51 )(R 52 )—*′, *—Ge(R 51 )(R 52 )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(R 51 )=*′, *═C(R 51 )—*′, *—C(R 51 )═C(R 52 )—*′, *—C(═S)—*′, or *—C≡C—*′,
T 2 in Formula 1 is a single bond, a double bond, *—N(R 53 )—*′, *—B(R 53 )—*′, *—P(R 53 )—*′, *—C(R 53 )(R 54 )—*′, *—Si(R 53 )(R 54 )—*′, *—Ge(R 53 )(R 54 )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(R 53 )=*′, *═C(R 53 )—*′, *—C(R 53 )═C(R 54 )—*′, *—C(═S)—*′, or *—C≡C—*′,
T 3 in Formula 1 is a single bond, a double bond, *—N(R 55 )—*′, *—B(R 55 )—*′, *—P(R 55 )—*′, *—C(R 55 )(R 56 )—*′, *—Si(R 55 )(R 56 )—*′, *—Ge(R 55 )(R 56 )—*′, *—S—*′,*—Se—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(R 55 )=*′, *═C(R 55 )—*′, *—C(R 55 )═C(R 56 )—*′, *—C(═S)—*′, or *—C≡C—*′,
Het1 in Formula 2 is a π-electron-deficient nitrogen-containing C 1 -C 30 cyclic group,
ring CY 71 and ring CY 72 in Formula 3-1 are each independently a π-electron-rich C 3 -C 30 cyclic group, ring CY 71 and ring CY 72 in Formula 3-1 are optionally linked to each other via a π-electron-rich C 3 -C 30 cyclic group unsubstituted or substituted with at least one R 10a ,
X 71 in Formula 3-1 is O, S, N-(L 75 ) b75 -(R 75 ) a75 , C(R 75 )(R 76 ), or Si(R 75 )(R 76 ),
L 79 in Formula 3-1 is a single bond, or a π-electron-rich C 3 -C 30 cyclic group unsubstituted or substituted with at least one R 10a ; or absent,
n in Formula 2 is one of an integer from 1 to 10,
m in Formula 3-1 is 1, 2, or 3, wherein, when m is 1, L 79 is absent,
L 1 to L 4 , L 61 , L 75 , and L 81 to L 87 in Formulae 1, 2, and 3-1 to 3-4 are each independently a single bond, a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,
b1 to b4, b61, b75, and b81 to b87 in Formulae 1, 2, and 3-1 to 3-4 are each independently an integer from 1 to 10,
R a , R b , R 1 to R 4 , R 51 to R 56 , R 61 , R 62 , R 71 , R 72 , R 75 , R 76 , and R 81 to R 86 in Formulae 1, 2, and 3-1 to 3-4 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), or —P(═O)(Q 8 )(Q 9 ),
c1 to c4 in Formula 1 are each independently an integer from 1 to 10,
a1 to a4, a61, a62, a71, a72, a75, and a81 to a86 in Formulae 1, 2, and 3-1 to 3-4 are each independently an integer from 0 to 20,
two or more of R a , R b , R 1 to R 4 , and R 51 to R 56 in Formula 1 are optionally linked to each other to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,
R 10a is the same as defined in

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Kim Sangdong
• Kwak Seungyeon
• Koo Hyun
• Kim Sungjun
• Kim Hyungsun
• Baik Chul
• Sim Myungsun
• Yang Yongtak
• Lee Banglin
• Lee Sunyoung
• Lee Sunghun
• Yi Jeoungin
• Cho Yuri
• Cho Pyeongseok
• Choi Byoungki
• Choi Hyeonho
• Huh Dalho
• Hong Seokhwan

Classifications

• H01L51/0087 Primary

  Electricity · mapped topic

• H01L2251/552

  Electricity · mapped topic

• H01L51/5072

  Electricity · mapped topic

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title