Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-10615348-B2
Application number	US-201615091172-A
Country	US
Kind code	B2
Filing date	Apr 5, 2016
Priority date	Nov 16, 2015
Publication date	Apr 7, 2020
Grant date	Apr 7, 2020

Abstract

An organic light-emitting device including a first electrode, a second electrode facing the first electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer, the emission layer includes a host and a fluorescent dopant, the organic light-emitting device satisfies Equation 1, the host includes a compound represented by Formulae 1, 2, or 3, and the fluorescent dopant satisfies Equation 2, wherein Formulae 1-3 and Equations 1-2 are the same as described in the specification.

First claim

What is claimed is:

1. An organic light-emitting device comprising:
a first electrode,
a second electrode facing the first electrode, and
an organic layer disposed between the first electrode and the second electrode, wherein
the organic layer comprises an emission layer,
the emission layer comprises a host and a delayed fluorescent dopant, wherein the delayed fluorescent dopant is a thermally activated delayed fluorescence (TADF) dopant,
the organic light-emitting device satisfies Equation 1,
the host comprises a compound represented by Formulae 1, 2, or 3, and
the delayed fluorescent dopant satisfies Equation 2:
0.2 electron Volts≤ E T1 ( H )− E T1 ( FD )≤0.5 electron Volts  Equation 1

0 electron Volts≤ E S1 ( FD )− E T1 ( FD )≤0.2 electron Volts,  Equation 2

wherein in Equation 1 and 2,
E T1 (H) is a triplet energy level of the host expressed in electron Volts,
E T1 (FD) is a triplet energy level of the delayed fluorescent dopant expressed in electron Volts,
E S1 (FD) is a singlet energy level of the delayed fluorescent dopant expressed in electron Volts, and
E T1 (H), E T1 (FD), and E S1 (FD) are evaluated by using a Density Functional Theory method of Gaussian program that is structurally optimized at a level of B3LYP/6-31G(d,p):

wherein Z 1 to Z 8 and Z 11 to Z 18 in Formula 1 are each independently selected from hydrogen, deuterium, and a cyano group (CN),
Z 21 to Z 24 in Formula 1 are each independently selected from hydrogen, deuterium, a cyano group, a group represented by Formula 2A, and a group represented by Formula 2B,
Z 31 to Z 40 in Formula 2 and Z 41 to Z 48 in Formula 3 are each independently selected from hydrogen, deuterium, a cyano group, and a group represented by Formula 2C, wherein at least two selected from Z 31 to Z 40 in Formula 2 and at least two selected from Z 41 to Z 48 in Formula 3 are each independently selected from groups represented by Formula 2C,
Z 51 to Z 55 in Formulae 2A to 2C are each independently hydrogen or deuterium,
a1 to a5 in Formulae 2A to 2C are each independently an integer selected from 0 to 4,
b1 in Formula 2A is an integer selected from 1 to 5,
b2 to b5 in Formulae 2B and 2C are each independently an integer selected from 0 to 4, provided that the sum of b2 and b3 is 1 or more,
* in Formulae 2A to 2C indicates a binding site to a neighboring atom, and the compound represented by Formula 1, the compound represented by Formula 2, and the compound represented by Formula 3 each independently comprise at least one cyano group,
wherein the delayed fluorescent dopant is a compound represented by Formula 11 or 14A:

wherein
ring A 1 in Formula 11 is a group represented by Formula 12A,
ring A 2 in Formula 11 is a group represented by Formula 12B,
X 1 in Formula 12B is O, or S,
L 1 and L 2 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,
c1 and c2 are each independently an integer selected from 0 to 4,
Ar 1 and Ar 2 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 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,
R 1 to R 10 are each independently selected from hydrogen, deuterium, 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 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 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, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 4 )(Q 5 ), and —B(Q 6 )(Q 7 ), and
at least one substituent selected from the substituted C 3 -C 10 cycloalkylene group, substituted C 1 -C 10 heterocycloalkylene group, substituted C 3 -C 10 cycloalkenylene group, substituted C 1 -C 10 heterocycloalkenylene group, substituted C 6 -C 60 arylene group, substituted C 1 -C 60 heteroarylene group, a substituted divalent non-aromatic condensed polycyclic group, a substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 alkyl group, substituted C 2 -C 60 alkenyl group, substituted C 2 -C 60 alkynyl group, substituted C 1 -C 60 alkoxy group, substituted C 3 -C 10 cycloalkyl group, substituted C 1 -C 10 heterocycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted C 1 -C 10 heterocycloalkenyl group, substituted C 6 -C 60 aryl group, substituted C 6 -C 60 aryloxy group, substituted C 6 -C 60 arylthio group, substituted heteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group and a substituted monovalent non-aromatic condensed heteropolycyclic group is selected from
deuterium, 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, 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, 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 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 condense

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Miyazaki Hiroshi
• Kang Hosuk
• Numata Masaki
• Ihn Sooghang
• Jeon Soonok
• Chae Miyoung

Classifications

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K11/025 Primary

  non-luminescent particle coatings or suspension media · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title