Search

US-12624061-B2 - Organic light-emitting device and electronic apparatus

US12624061B2US 12624061 B2US12624061 B2US 12624061B2US-12624061-B2

Abstract

An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer includes an emission layer, the emission layer includes a first host, a first dopant, and a second dopant, and the first dopant is an organometallic compound the first dopant represented by one of Formulae 40 and 50 and including metal having an atomic weight of 40 or greater:

Inventors

  • Seokgyu Yoon
  • Jinwon SUN
  • Hyosup Shin
  • Hyeongu CHO

Assignees

  • SAMSUNG DISPLAY CO., LTD.

Dates

Publication Date
20260512
Application Date
20200325
Priority Date
20190328

Claims (14)

  1. 1 . An organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises an emission layer, the emission layer comprises a first host, a first dopant, and a second dopant, wherein the first dopant is an organometallic compound selected from among Compounds 50-11 to 50-15, 50-21 to 50-28, 50-39 to 50-43, 50-49 to 50-56, 50-67 to 50-71, and 50-77 to 50-84, wherein the second dopant comprises a heterocyclic compound represented by one of Formula 11(4) or Formula 501: wherein, in Compounds 50-11 to 50-15, 50-21 to 50-28, 50-39 to 50-43, 50-49 to 50-56, 50-67 to 50-71, and 50-77 to 50-84, “Me” represents a methyl group, “iso-Pr” represents an iso-propyl group, and “tert-Bu” represents a t-butyl group, and wherein, in Formula 11(4), CY 11 to CY 13 are each independently a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, Y 11 and Y 12 are each independently at least one of a single bond, —O—, —S—, —C(R 14 )(R 15 )—, —N(R 14 )—, Si(R 14 )(R 15 )—, —C(═O)—, —S(═O) 2 —, —B(R 14 )—, or —P(═O)(R 14 )—, at least one selected from among Y 11 or Y 12 is each independently at least one of —C(R 14 )(R 15 )—, —N(R 14 )—, Si(R 14 )(R 15 )—, —C(═O)—, —S(═O) 2 —, —B(R 14 )—, or —P(═O)(R 14 )—, Y 15 is N, B, or P, R 11 to R 15 are each independently at least one of hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano 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 C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio 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 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ), at least two substituents selected from R 11 to R 15 are optionally bound to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group, R 14 is bound to at least one of R 11 or R 13 to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group, or Formula 11(4) is represented by Compound 12-1 or Compound 12-2: a11 to a13 are each independently an integer from 1 to 6, and at least one substituent of the substituted C 5 -C 60 carbocyclic group, the substituted C 1 -C 60 heterocyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted C 1 -C 60 heteroaryloxy group, the substituted C 1 -C 60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, or the substituted monovalent non-aromatic condensed heteropolycyclic group is at least one of: deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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; 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 substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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, —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 ), or —P(═O)(Q 11 )(Q 12 ); 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, or a monovalent non-aromatic condensed heteropolycyclic 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, or a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 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, —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 ), or —P(═O)(Q 21 )(Q 22 ); 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 ), 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 at least one of hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 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 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, or a terphenyl group, wherein, in Formula 501, Ar 501 is selected from a substituted or unsubstituted C 5 -C 60 carbocyclic group and a substituted or unsubstituted C 1 -C 60 heterocyclic group, L 501 to L 503 are each independently at least one of 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, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group, xd1 to xd3 are each independently an integer from 0 to 3, R 501 and R 502 are each independently at least one of 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, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and xd4 is an integer from 1 to 6.
  2. 2 . The organic light-emitting device of claim 1 , wherein the first dopant and the second dopant each satisfy Equations 1-1 and 1-2: S 1( D 1) onset ≥S 1( D 2) onset Equation 1-1 S 1( D 1) max ≥S 1( D 2) max , Equation 1-2 wherein, in Equations 1-1 and 1-2, S1(D1) onset indicates a singlet energy at an onset wavelength (λ onset ) in a photoluminescence (PL) spectrum of the first dopant, S1(D2) onset indicates a singlet energy at an onset wavelength in a PL spectrum of the second dopant, S1(D1) max indicates a singlet energy at a maximum emission wavelength (λ max ) in a PL spectrum of the first dopant, and S1(D2) max indicates a singlet energy at a maximum emission wavelength in a PL spectrum of the second dopant.
  3. 3 . The organic light-emitting device of claim 1 , wherein the first dopant and the second dopant satisfy Equation 2-1: S 1( D 1) onset −S 1( D 2) onset ≤0.2 eV, Equation 2-1 wherein, in Equation 2-1, S1(D1) onset indicates a singlet energy level at an onset wavelength (λ onset ) in a photoluminescence (PL) spectrum of the first dopant, and S1(D2) onset indicates a singlet energy level at an onset wavelength in a PL spectrum of the second dopant.
  4. 4 . The organic light-emitting device of claim 1 , wherein the first dopant and the second dopant satisfy Equation 2-2: T 1( D 1) onset −T 1( D 2) onset ≤0.2 eV, Equation 2-2 wherein, in Equation 2-2, T1(D1) onset indicates a triplet energy at an onset wavelength in a photoluminescence (PL) spectrum of the first dopant, and T1(D2) onset indicates a triplet energy at an onset wavelength in a PL spectrum of the second dopant.
  5. 5 . The organic light-emitting device of claim 1 , wherein the emission layer is configured to emit blue light having a maximum emission wavelength of about 420 nanometers (nm) or greater to about 470 nm or less.
  6. 6 . The organic light-emitting device of claim 1 , wherein a ratio of an emission component emitted from the second dopant to total emission components from the emission layer is 50 percent (%) or greater.
  7. 7 . The organic light-emitting device of claim 1 , wherein the emission layer consists of the first host, the first dopant, and the second dopant.
  8. 8 . The organic light-emitting device of claim 1 , wherein the second dopant is a delayed fluorescence dopant that satisfies Equation 3-2: S 1( D 2)− T 1( D 2)≤0.3 eV, Equation 3-2 wherein, in Equation 3-2, S1(D2) indicates a singlet energy of the second dopant, and T1(D2) indicates a triplet energy of the second dopant.
  9. 9 . The organic light-emitting device of claim 1 , wherein CY 11 to CY 13 are each independently at least one of a benzene group, a naphthalene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group, and R 11 to R 15 are each independently at least one of hydrogen, deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, iso-butyl group, a tert-butyl group, an ethenyl group, a propenyl group, a butenyl group, a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, a sec-butoxy group, an iso-butoxy group, a tert-butoxy group, a phenyl group, a biphenyl group, or a group represented by one of Formulae 4-1 to 4-34, Formulae 5-1 to 5-26, and Formulae 6-1 to 6-55: wherein, in Formulae 4-1 to 4-34, Formulae 5-1 to 5-26, and Formulae 6-1 to 6-55, Y 21 and Y 22 are each independently O, S, C(Z 26 )(Z 27 ), N(Z 26 ), or Si(Z 26 )(Z 27 ), Y 23 to Y 26 are each independently a single bond, O, S, C(Z 28 )(Z 29 ), N(Z 28 ), or Si(Z 28 )(Z 29 ), Y 27 is N, B, or P, Y 31 and Y 32 are each independently O, S, C(Z 33 )(Z 34 ), N(Z 33 ), or Si(Z 33 )(Z 34 ), Z 21 to Z 29 and Z 31 to Z 34 are each independently at least one of hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl 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, a dibenzofuranyl group, a dibenzothiophenyl group, a triazinyl group, a benzimidazolyl group, a phenanthrolinyl group, and —Si(Q 31 )(Q 32 )(Q 33 ), wherein Q 31 to Q 33 are each independently selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, g2 is 1 or 2, g3 is an integer from 1 to 3, g4 is an integer from 1 to 4, g5 is an integer from 1 to 5, g7 is an integer from 1 to 7, g8 is an integer from 1 to 8, e2 is 1 or 2, e3 is an integer from 1 to 3, e4 is an integer from 1 to 4, e5 is an integer from 1 to 5, e6 is an integer from 1 to 6, e7 is an integer from 1 to 7, e9 is an integer from 1 to 9, and * indicates a binding site to an adjacent atom.
  10. 10 . The organic light-emitting device of claim 1 , wherein the second dopant is selected from Compounds FD1 to FD23:
  11. 11 . The organic light-emitting device of claim 1 , wherein the first electrode is an anode, the second electrode is a cathode, the organic layer 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 a combination thereof, and the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
  12. 12 . The organic light-emitting device of claim 11 , wherein the hole transport region comprises a p-dopant, wherein a lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant is −3.5 electron volts (eV) or less.
  13. 13 . The organic light-emitting device of claim 11 , wherein the electron transport region comprises a metal-containing material.
  14. 14 . An electronic apparatus comprising: an organic light-emitting device according to claim 1 and a thin-film transistor, wherein the first electrode of the organic light-emitting device is electrically connected to one of a source electrode or a drain electrode of the thin-film transistor.

Description

CROSS-REFERENCE TO RELATED APPLICATION This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0036222, filed on Mar. 28, 2019, in the Korean Intellectual Property Office, the entire content of which is incorporated herein by reference. BACKGROUND 1. Field One or more aspects of embodiments of the present disclosure are directed toward to an organic light-emitting device and an electronic apparatus including the organic light-emitting device. 2. Description of the Related Art Organic light-emitting devices (OLEDs) are self-emission devices that, as compared with related devices, have wide viewing angles, high contrast ratios, short response times, and/or excellent characteristics in terms of brightness, driving voltage, and/or response speed, and can produce full-color images. OLEDs may include a first electrode on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region. Electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, may then recombine in the emission layer to produce excitons. These excitons transition from an excited state to a ground state to thereby generate light. SUMMARY One or more aspects of embodiments of the present disclosure are directed toward an organic light-emitting device having a low driving voltage, excellent external quantum efficiency, and improved lifespan characteristics, and an electronic device including the organic light-emitting device. Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments. According to one or more embodiments, an organic light-emitting device may include a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer may include an emission layer, the emission layer may include a first host, a first dopant, and a second dopant, and the first dopant may be an organometallic compound including a metal having an atomic weight of 40 or greater. According to one or more embodiments, an electronic apparatus may include the organic light-emitting device and a thin-film transistor, wherein the first electrode of the organic light-emitting device may be electrically connected to one selected from a source electrode and a drain electrode of the thin-film transistor. BRIEF DESCRIPTION OF THE DRAWINGS These and/or other aspects will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawings in which: FIG. 1 is a schematic cross-sectional view illustrating an organic light-emitting device according to an embodiment; FIG. 2 is a schematic cross-sectional view illustrating an organic light-emitting device according to an embodiment; FIG. 3 is a schematic cross-sectional view illustrating an organic light-emitting device according to an embodiment; FIG. 4 is a schematic cross-sectional view illustrating an organic light-emitting device according to an embodiment; and FIG. 5 is a schematic view of an energy relationship between a first host, a first dopant, and a second dopant included in an emission layer of an organic light-emitting device according to an embodiment. FIG. 6 is a schematic view illustrating an electronic apparatus according to an embodiment. DETAILED DESCRIPTION Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects of the present description. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” “one of,” and “selected from,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list. Further, the use of “may” when describing embodiments of the present invention may refer to “one or more embodiments of the present invention.” As the inventive concept allows for various modifications and includes various embodiments, example embodiments will be illustrated in the drawings and described in more detail in the written description. Effects, features, and a method of achieving the inventive concept should become apparent by reference to the example em