Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-10396296-B2
Application number	US-201715602581-A
Country	US
Kind code	B2
Filing date	May 23, 2017
Priority date	Jul 13, 2016
Publication date	Aug 27, 2019
Grant date	Aug 27, 2019

Abstract

An organic light-emitting device includes electrodes and light-emitting units that each include an emission layer; and a charge generation layer, including n- and p-type charge generation layers, disposed between each adjacent pair of light-emitting units. A wavelength of maximum intensity of light emitted from one of the light-emitting units may be different from another, an n-type charge generation layer may have a metal-containing material having a work function of about 2.0 eV to about 4.5 eV, and a p-type charge generation layer may be formed of a hole transport material, an absolute value of a HOMO energy level of the hole transport material being greater than about 5.5 eV, and an absolute value of a LUMO energy level of the hole transport material being less than that of a LUMO energy level of a hole transport layer of a light-emitting unit adjacent to the p-type charge generation layer.

First claim

What is claimed is:

1. An organic light-emitting device, comprising:
a first electrode, a second electrode facing the first electrode, and a plurality of light-emitting units disposed in a stack between the first and second electrodes, each light emitting unit including an emission layer; and
a charge generation layer, including an n-type charge generation layer and a p-type charge generation layer, disposed between each adjacent pair of light-emitting units, wherein:
a wavelength of maximum intensity of light emitted from one of the light-emitting units is different from the wavelength of maximum intensity of light emitted from another of the light-emitting units,
at least one n-type charge generation layer consists of a metal-containing material having a work function of about 2.0 eV to about 4.5 eV, the metal-containing material being a metal, a metal oxide, a metal halide, or a combination thereof, and
at least one p-type charge generation layer includes a hole transport material,
at least one light-emitting unit adjacent to the p-type charge generation layer including the hole transport material includes a hole transport region,
the hole transport region includes a hole transport layer,
an absolute value of a highest occupied molecular orbital (HOMO) energy level of the hole transport material being greater than about 5.5 eV, and an absolute value of a lowest unoccupied molecular orbital (LUMO) energy level of the hole transport material being less than that of a LUMO energy level of a hole transport layer of a light-emitting unit adjacent to the p-type charge generation layer.

2. The organic light-emitting device as claimed in claim 1 , wherein the metal-containing material has a work function of about 2.5 eV to about 4.0 eV.

3. The organic light-emitting device as claimed in claim 1 , wherein the metal-containing material includes at least one selected from ytterbium (Yb), silver (Ag), aluminum (Al), samarium (Sm), magnesium (Mg), lithium (Li), RbI, titanium (Ti), rubidium (Rb), sodium (Na), potassium (K), barium (Ba), manganese (Mn), and YbSi 2 .

4. The organic light-emitting device as claimed in claim 1 , wherein the absolute value of the HOMO energy level of the hole transport material is greater than an absolute value of a HOMO energy level of the hole transport layer.

5. The organic light-emitting device as claimed in claim 1 , wherein the absolute value of the HOMO energy level of the hole transport material is about 5.5 eV to about 7.0 eV.

6. The organic light-emitting device as claimed in claim 1 , wherein the hole transport material is formed from compounds that do not have a cyano group, the absolute value of the HOMO energy level of the hole transport material being about 5.5 eV to about 7.0 eV.

7. The organic light-emitting device as claimed in claim 1 , wherein the hole transport material is selected from an amine-containing compound and a carbazole-containing compound, the absolute value of the HOMO energy level of the hole transport material being about 5.5 eV to about 7.0 eV.

8. The organic light-emitting device as claimed in claim 1 , wherein the hole transport material is selected from compounds represented by Formulae 201, 202, and 301-2:

wherein, in Formulae 201, 202, and 301-2,
A 301 to A 304 are each independently selected from a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a pyridine group, a pyrimidine group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, an indole group, a carbazole group, a benzocarbazole group, a dibenzocarbazole group, a furan group, a benzofuran group, a dibenzofuran group, a naphthofuran group, a benzonaphthofuran group, a dinaphthofuran group, a thiophene group, a benzothiophene group, a dibenzothiophene group, a naphthothiophene group, a benzonaphthothiophene group, and a dinaphthothiophene group,
X 301 is O, S, or N-[(L 304 ) xb4 -R 304 ],
L 201 to L 204 and L 301 to L 303 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,
L 205 is selected from *—O—*′, *—S—*′, *—N(Q 201 )-*′, a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 2 -C 20 alkenylene group, 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,
xa1 to xa4 are each independently an integer of 0 to 3,
xa5 is an integer of 1 to 10,
xb1 to xb4 are each independently an integer of 0 to 5,
xb22 and xb23 are each independently 0, 1, or 2,
R 201 to R 204 and Q 201 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,
R 301 to R 304 are each independently selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 301 )(Q 302 )(Q 303 ), —N(Q 301 )(Q 302 ), —B(Q 301 )(Q 302 ), —C(═O)(Q 301 ), —S(═O) 2 (Q 301 ), and —P(═O)(Q 301 )(Q 302 ),
R 311 to R 314 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl

Assignees

• Samsung Display Co Ltd

Inventors

• Ko Heejoo

Classifications

• C07C2601/14

  The ring being saturated · CPC title

• C07C211/54

  having amino groups bound to two or three six-membered aromatic rings · CPC title

• H01L51/5004

  Electricity · mapped topic

• H01L51/508

  Electricity · mapped topic

• H01L51/504

  Electricity · mapped topic