Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-11043646-B2
Application number	US-201615134956-A
Country	US
Kind code	B2
Filing date	Apr 21, 2016
Priority date	Sep 7, 2015
Publication date	Jun 22, 2021
Grant date	Jun 22, 2021

Abstract

An organic light-emitting device including: a first electrode, a hole transport region including a first hole transport layer (HTL), an emission layer, an electron transport region; and a second electrode; wherein the first HTL includes a first compound and a second compound, the emission layer includes a third compound and a fourth compound, the electron affinity of the second compound is greater than the electron affinity of the first compound, a lowest unoccupied molecular orbital (LUMO) energy level of the fourth compound is greater than a LUMO energy level of the third compound, the second compound and the third compound are different from each other, and the minimum anionic dissociation energy of the second compound is greater than the triplet energy of the third compound.

First claim

What is claimed is:

1. An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode;
an emission layer between the first electrode and the second electrode;
a hole transport region between the first electrode and the emission layer, the hole transport region comprising a first hole transport layer directly contacting the emission layer; and
an electron transport region between the second electrode and the emission layer,
wherein the first hole transport layer comprises a first compound and a second compound,
the emission layer comprises a third compound and a fourth compound,
an electron affinity of the second compound is greater than an electron affinity of the first compound,
a lowest unoccupied molecular orbital (LUMO) energy level of the fourth compound is greater than a LUMO energy level of the third compound,
the second compound and the third compound are different from each other,
a minimum anionic decomposition energy of the second compound is greater than a triplet energy of the third compound, and
the second compound is represented by one selected from Compounds 1, 2, and 4:

wherein a weight ratio of the first compound to the second compound is 99:1 to 50:50.

2. The organic light-emitting device of claim 1 , wherein a difference between the electron affinity of the second compound and the electron affinity of the first compound is 0.2 eV or greater.

3. The organic light-emitting device of claim 1 , wherein a difference between the LUMO energy level of the fourth compound and the LUMO energy level of the third compound is 0.1 eV or greater.

4. The organic light-emitting device of claim 1 , wherein a difference between the minimum anionic decomposition energy of the second compound and the triplet energy of the third compound is 0.1 eV or greater.

5. The organic light-emitting device of claim 1 , wherein the minimum anionic decomposition energy of the second compound is greater than a singlet energy of the fourth compound.

6. The organic light-emitting device of claim 1 , wherein the first compound is selected from m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD, TCTA, and compounds represented by Formulae 1A and 1B:

wherein, in Formulae 1A and 1B,
L 11 to L 15 are each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
a11 to a14 are each independently selected from 0, 1, 2, and 3,
a15 is selected from 1, 2, 3, 4, and 5, and
R 11 to R 14 are each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -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, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

7. The organic light-emitting device of claim 1 , wherein the first compound is represented by one selected from Compounds HT1 to HT20:

8. The organic light-emitting device of claim 1 , wherein the third compound is represented by Formula 3:
Ar 31 −[(L 31 ) a31 −R 31 ] b31 ,  Formula 3

wherein, in Formula 3,
Ar 31 is selected from an anthracene and an indenoanthracene; and
an anthracene and an indenoanthracene, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino 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 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 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, and —Si(Q 31 )(Q 32 )(Q 33 ),
L 31 is selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
a31 is selected from 0, 1, 2, and 3,
R 31 is selected from:
a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group;
a C 1 -C 20 alkyl group and a C 1 -C 20 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 amino 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 phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benz

Assignees

• Samsung Display Co Ltd

Inventors

• Lee Sunghun
• Kim Seulong
• Park Illsoo
• Shin Hyosup
• Kang Sunwoo
• Koh Eunkyung
• Kim Minkyung
• Kim Taekyung
• Lee Jaeyong

Classifications

• H10K2101/40 Primary

  Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H01L2251/552

  Electricity · mapped topic

• H01L51/006

  Electricity · mapped topic

• H01L51/5064

  Electricity · mapped topic