Organic light emitting device and display device including the same
By introducing a triplet exciton quenching layer into the organic light emitting device, the problems of reduced efficiency and short life of organic light emitting devices in the prior art are solved, and high-efficiency and long-life luminous performance are achieved.
Patent Information
- Application Number
- CN201811548326.2
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2017-12-18
- Filing Date
- 2018-12-18
- Publication Date
- 2025-02-28
- Estimated Expiration
- 2038-12-18
AI Technical Summary
The efficiency of existing organic light emitting devices decreases after long-term use and short life, making it difficult to extend their service life while maintaining high efficiency.
A triplet exciton quenching layer is introduced into an organic light emitting device, through which triplet excitons are quenched, thereby reducing the junction between the exciton recombination region and the exciton quenching region and extending the lifetime of the light emitting device.
It effectively prevents the efficiency of organic light-emitting devices from being reduced, extends its service life, and maintains efficient light-emitting performance.
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Figure CN109994637B_ABST
Abstract
Description
[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2017-0174430 filed on December 18, 2017, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field
[0002] One or more embodiments relate to an organic light emitting device and a display apparatus including the same. Background Art
[0003] Organic light emitting devices are self-emissive devices that produce full-color images and also have wide viewing angles, high contrast, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed compared to devices in the art.
[0004] An example of such an organic light-emitting device may include a first electrode disposed on a substrate and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially disposed on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. These excitons transition (e.g., relax) from an excited state to a ground state, thereby generating light. Summary of the invention
[0005] Aspects of embodiments of the present disclosure provide an organic light-emitting device including a triplet exciton quenching layer.
[0006] Additional aspects of the embodiments will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented embodiments.
[0007] An aspect of an embodiment provides an organic light emitting device, the organic light emitting device comprising:
[0008] a first electrode;
[0009] a second electrode facing the first electrode; and
[0010] The organic layer is located between the first electrode and the second electrode and includes an emission layer and a triplet exciton quenching layer.
[0011] Another aspect of the embodiment provides a display device, the display device comprising:
[0012] A thin film transistor comprising a source electrode, a drain electrode and an active layer; and
[0013] The organic light-emitting device,
[0014] Here, the first electrode of the organic light emitting device is electrically coupled to (eg, electrically connected to) one selected from a source electrode and a drain electrode of the thin film transistor. BRIEF DESCRIPTION OF THE DRAWINGS
[0015] These and / or other aspects of the embodiments will become apparent and more readily understood through the following description of the embodiments in conjunction with the accompanying drawings, in which:
[0016] Figure 1 is a schematic diagram of an organic light emitting device according to an embodiment;
[0017] Figure 2 is a diagram showing relative energy levels of a host and a dopant in an emission layer of an organic light emitting device according to an embodiment;
[0018] Figure 3 is a diagram showing relative energy levels of a host and a dopant in an emission layer of an organic light emitting device according to another embodiment;
[0019] Figure 4 is a graph showing results obtained by measuring lifespans of organic light emitting devices manufactured according to Examples 1 and 2 and Comparative Example 1; and
[0020] Figure 5 is a graph showing results obtained by measuring delayed triplet exciton components of organic light emitting devices manufactured according to Examples 1 and 2 and Comparative Example 1 by using transient electroluminescence (EL). DETAILED DESCRIPTION
[0021] The subject matter of the present disclosure will now be more fully described with reference to exemplary embodiments. However, the present disclosure may be implemented in many different forms and should not be construed as being limited to the embodiments set forth herein; on the contrary, these embodiments are provided so that the present disclosure will be thorough and complete and will fully convey the disclosed concepts to those skilled in the art. Here, by reference to the embodiments and drawings that will be described in more detail below, the features of the present disclosure and how to achieve them will become apparent. However, the subject matter of the present disclosure may be implemented in many different forms and should not be limited to exemplary embodiments.
[0022] Hereinafter, embodiments are described in more detail by referring to the accompanying drawings, in which like reference numerals denote like elements and redundant explanation thereof is unnecessary.
[0023] As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.
[0024] It will also be understood that the term “comprises” and / or variations thereof used herein specify the presence of stated features or components, but do not preclude the presence or addition of one or more other features or components.
[0025] It will be understood that when a layer, region or component is referred to as being "on" or "to" another layer, region or component, the layer, region or component may be directly or indirectly formed on the other layer, region or component. For example, there may be intermediate layers, intermediate regions or intermediate components.
[0026] For convenience of explanation, the sizes of components in the drawings may be exaggerated. In other words, since the sizes and thicknesses of components in the drawings may be arbitrarily shown for convenience of explanation, the following embodiments of the present disclosure are not limited thereto.
[0027] According to an embodiment, an organic light emitting device includes:
[0028] a first electrode;
[0029] a second electrode facing the first electrode; and
[0030] The organic layer is located between the first electrode and the second electrode and includes an emission layer and a triplet exciton quenching layer.
[0031] As used herein, the term "organic layer" refers to a single layer and / or a plurality of layers disposed between a first electrode and a second electrode of an organic light emitting device. Materials included in the "organic layer" are not limited to organic materials.
[0032] As used herein, the term "triplet exciton quenching layer" may refer to a layer that quenches triplet excitons formed in an emission layer.
[0033] Since the triplet exciton quenching layer exists as a layer separated from the emission layer, the region where the excitons recombine (hereinafter, referred to as the "exciton recombination region") can be separated from the region where the triplet excitons are quenched. Therefore, when the organic light-emitting device includes the triplet exciton quenching layer, the life of the organic light-emitting device can be increased without reducing (or substantially reducing) the efficiency of the organic light-emitting device.
[0034] Figure 1 1 is a schematic diagram of an organic light emitting device 10 according to an embodiment. The organic light emitting device 10 includes a first electrode 110 , an organic layer 150 , and a second electrode 190 .
[0035] In the following, we will combine Figure 1 A structure of an organic light emitting device 10 and a method of manufacturing the organic light emitting device 10 according to an embodiment are described.
[0036] [First electrode 110]
[0037] exist Figure 1 In the embodiment, a substrate may be additionally disposed under the first electrode 110 or on the second electrode 190. The substrate may be a glass substrate or a plastic substrate, both of which have excellent mechanical strength, thermal stability, transparency, surface flatness, easy handling, and waterproofness.
[0038] The first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for the first electrode 110 may be selected from materials having a high work function to facilitate hole injection.
[0039] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and any combination thereof, but the embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 110 may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but the embodiments of the present disclosure are not limited thereto.
[0040] The first electrode 110 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited thereto.
[0041] Organic layer 150
[0042] The organic layer 150 is disposed on the first electrode 110. The organic layer 150 may include an emission layer and a triplet exciton quenching layer.
[0043] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 190 .
[0044] The triplet exciton quenching layer may be disposed between the emission layer and the hole transport region, or may be disposed between the emission layer and the electron transport region.
[0045] In one embodiment, (i) the exciton recombination zone in the emission layer may be disposed at the interface between the emission layer and the electron transport region, and the triplet exciton quenching layer may be disposed between the emission layer and the hole transport region; or
[0046] (ii) The exciton recombination zone in the emission layer may be disposed at an interface between the emission layer and the hole transporting zone, and the triplet exciton quenching layer may be disposed between the emission layer and the electron transporting zone.
[0047] In this way, since the exciton recombination region in the emission layer is formed close to the electron transport region or the hole transport region, and the triplet exciton quenching layer is disposed on the side of the emission layer opposite to the side on which the exciton recombination region in the emission layer is formed, the triplet exciton quenching layer may not quench singlet excitons, but may selectively quench triplet excitons instead. Therefore, the reduction in efficiency of the organic light-emitting device may be more effectively prevented or reduced.
[0048] Hole transport region in the organic layer 150
[0049] The hole transport region may have: i) a single layer structure including a single layer including a single material; ii) a single layer structure including a single layer including a plurality of different materials; or iii) a multilayer structure having a plurality of layers including a plurality of different materials.
[0050] The hole transport region may include at least one layer selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.
[0051] For example, the hole transport region may have: a single-layer structure including a single layer containing a plurality of different materials; or a multilayer structure having a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure or a hole injection layer / hole transport layer / emission assisting layer structure, wherein, for each structure, the constituent layers are stacked sequentially from the first electrode 110 in the order stated, but the structure of the hole transport region is not limited thereto.
[0052] The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, and a compound represented by Formula 202:
[0053]
[0054]
[0055] Formula 201
[0056]
[0057] Formula 202
[0058]
[0059] In equation 201 and equation 202,
[0060] L 201 To L 204 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0061] L 205 Can be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C 1 -C 20 Alkylene, substituted or unsubstituted C 2 -C 20 Alkenylene, substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0062] xa1 to xa4 may each independently be an integer from 0 to 3,
[0063] xa5 can be an integer from 1 to 10,
[0064] R 201 To R 204 and Q 201 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, 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.
[0065] In one embodiment, in Formula 202, R 201 and R 202 can be optionally linked via a single bond, a dimethyl-methylene or a diphenyl-methylene, R 203 and R 204 Attachment may alternatively be via a single bond, a dimethyl-methylene group or a diphenyl-methylene group.
[0066] In one or more embodiments, in equation 201 and equation 202,
[0067] L 201 To L 205 Can be independently selected from:
[0068] Phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, rubidinylene, camphenylene, ovaphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene, and pyridinylene; and
[0069] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ) is at least one of phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalene, indacenylene, acenaphthenylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, rubidinylene, camphenylene, ovphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene and pyridylene,
[0070] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0071] In one or more embodiments, xa1 to xa4 may each independently be 0, 1 or 2.
[0072] In one or more embodiments, xa5 can be 1, 2, 3 or 4.
[0073] In one or more embodiments, R 201 To R 204 and Q 201 can be independently selected from: phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridyl; and
[0074] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32) is phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl and pyridyl,
[0075] Q 31 To Q 33 may all independently be the same as described above.
[0076] In one or more embodiments, in Formula 201, from R 201 To R 203 At least one of the selected ones can be independently selected from:
[0077] fluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and
[0078] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 an alkyl group of phenyl, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group,
[0079] However, the embodiments of the present disclosure are not limited thereto.
[0080] In one or more embodiments, in Formula 202, i) R 201 and R 202 can be connected via a single bond, and / or ii) R 203 and R 204 Connection can be made via a single button.
[0081] In one or more embodiments, in Formula 202, from R 201 To R 204 At least one of the selected ones may be selected from:
[0082] carbazolyl; and
[0083] The substitution is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 a carbazolyl group selected from at least one of a phenyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,
[0084] However, the embodiments of the present disclosure are not limited thereto.
[0085] The compound represented by Formula 201 can be represented by Formula 201A:
[0086] Formula 201A
[0087]
[0088] In one embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A(1), but embodiments of the present disclosure are not limited thereto:
[0089] Formula 201A(1)
[0090]
[0091] In one embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A-1, but the embodiments of the present disclosure are not limited thereto:
[0092] Formula 201A-1
[0093]
[0094] In one embodiment, the compound represented by Formula 202 can be represented by Formula 202A:
[0095] Formula 202A
[0096]
[0097] In one embodiment, the compound represented by Formula 202 can be represented by Formula 202A-1:
[0098] Formula 202A-1
[0099]
[0100] In Formula 201A, Formula 201A(1), Formula 201A-1, Formula 202A, and Formula 202A-1,
[0101] L 201 To L 203 , xa1 to xa3, xa5 and R 202 To R 204 may all independently be the same as described above,
[0102] R 211 and R 212 Can be combined with R 203 Same as described,
[0103] R 213 To R 217 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl and pyridyl.
[0104] The hole transport region may include at least one compound selected from Compound HT1 to Compound HT39, but the embodiments of the present disclosure are not limited thereto:
[0105]
[0106]
[0107]
[0108] The thickness of the hole transport region can be approximately To about In the range of, for example, about To about When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in the range of about To about In the range of, for example, about To about In the range of To about In the range of, for example, about To about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, suitable or satisfactory hole transport characteristics may be obtained without significantly increasing the driving voltage.
[0109] The emission auxiliary layer can improve light emitting efficiency by compensating the optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer can block the flow of electrons from the electron transport region. The emission auxiliary layer and the electron blocking layer can include materials as described above.
[0110] p-dopant
[0111] In addition to these materials, the hole transport region may also include a charge generating material for improving the conductive property. The charge generating material may be dispersed uniformly or non-uniformly in the hole transport region.
[0112] The charge generating material may be, for example, a p-dopant.
[0113] In one or more embodiments, the p-dopant can have a lowest unoccupied molecular orbital (LUMO) energy level of about -3.5 eV or less.
[0114] In one or more embodiments, the hole transport region may include an electron blocking layer, and the electron blocking layer may include a p-dopant having a LUMO energy level of about −3.5 eV or less.
[0115] The p-dopant may include at least one selected from quinone derivatives, metal oxides, and cyano-containing compounds, but the embodiments of the present disclosure are not limited thereto.
[0116] For example, the p-dopant may include at least one selected from the following compounds:
[0117] Quinone derivatives, such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);
[0118] Metal oxides, such as tungsten oxide or molybdenum oxide;
[0119] 1,4,5,8,9,12-Hexaazatriphenylene-hexanitrile (HAT-CN); and
[0120] The compound represented by formula 221,
[0121] However, the embodiments of the present disclosure are not limited thereto:
[0122] HAT-CN F4-TCNQ
[0123]
[0124] Formula 221
[0125]
[0126] In formula 221,
[0127] R 221 To R 223 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein R 221 To R 223 at least one selected from cyano, -F, -Cl, -Br, -I, C substituted with -F 1 -C 20 Alkyl, C substituted with -Cl 1 -C 20 Alkyl, C substituted with -Br 1 -C 20 Alkyl and C substituted with -I 1 -C 20 At least one substituent selected from the group consisting of:
[0128] [Emission Layer and Triplet Exciton Quenching Layer in Organic Layer 150]
[0129] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, or a blue emission layer according to the sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, wherein the two or more layers are in contact with each other or separated from each other. In one or more embodiments, the emission layer may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.
[0130] In one embodiment, the emissive layer may include a host and a dopant, and the host may include a fluorescent dopant.
[0131] In one embodiment,
[0132] (i) The highest occupied molecular orbital (HOMO) energy level of the host (E HH ), the lowest unoccupied molecular orbital (LUMO) energy level of the host (E HL ), the HOMO energy level of the fluorescent dopant (E DH ) and the LUMO energy level of the fluorescent dopant (E DL ) satisfies |E DH |>|E HH | and|E DL |>|E HL |,
[0133] A triplet exciton quenching layer is disposed between the emission layer and the electron transport region; or
[0134] (ii) The HOMO energy level of the host (E HH ), the LUMO energy level of the main body (E HL ), the HOMO energy level of the fluorescent dopant (E DH ) and the LUMO energy level of the fluorescent dopant (E DL ) satisfies |E DH |<|E HH | and|E DL |<|E HL |,
[0135] The triplet exciton quenching layer may be disposed between the emission layer and the hole transport region.
[0136] In one embodiment,
[0137] (i) The HOMO energy level of the host (E HH ), the LUMO energy level of the main body (E HL ), the HOMO energy level of the fluorescent dopant (E DH) and the LUMO energy level of the fluorescent dopant (E DL ) satisfies |E DH |>|E HH | and|E DL |>|E HL |,
[0138] The electron transport region includes a hole blocking layer,
[0139] The triplet exciton quenching layer may be disposed between the emission layer and the hole blocking layer.
[0140] In this case, for example, the triplet exciton quenching layer may be in direct contact with the emission layer and the hole blocking layer (eg, may directly contact the emission layer and the hole blocking layer).
[0141] In one or more embodiments,
[0142] (ii) The HOMO energy level of the host (E HH ), the LUMO energy level of the main body (E HL ), the HOMO energy level of the fluorescent dopant (E DH ) and the LUMO energy level of the fluorescent dopant (E DL ) satisfies |E DH |<|E HH | and|E DL |<|E HL |,
[0143] The hole transport region includes an electron blocking layer,
[0144] The triplet exciton quenching layer may be disposed between the emission layer and the electron blocking layer.
[0145] In this case, for example, the triplet exciton quenching layer may be in direct contact with the emission layer and the electron blocking layer.
[0146] Reference Figure 2 , when the HOMO energy level (E HH ), the LUMO energy level of the main body (E HL ), the HOMO energy level of the fluorescent dopant (E DH ) and the LUMO energy level of the fluorescent dopant (E DL ) satisfies |E DH |>|E HH | and|E DL |>|E HL|, the exciton recombination region in the emission layer is formed close to the hole transport region in the organic layer. In this case, since the triplet exciton quenching layer is disposed between the emission layer and the electron transport region, the triplet exciton quenching layer does not quench singlet excitons, but instead selectively quenches triplet excitons. Therefore, a fluorescent device with a long lifespan can be realized while more effectively preventing or reducing the reduction in efficiency of the organic light-emitting device.
[0147] Reference Figure 3 , when the HOMO energy level (E HH ), the LUMO energy level of the main body (E HL ), the HOMO energy level of the fluorescent dopant (E DH ) and the LUMO energy level of the fluorescent dopant (E DL ) satisfies |E DH |<|E HH | and|E DL |<|E HL |, the exciton recombination region in the emission layer is formed close to the electron transport region in the organic layer. In this case, since the triplet exciton quenching layer is disposed between the emission layer and the hole transport region, the triplet exciton quenching layer does not quench singlet excitons, but instead selectively quenches triplet excitons. Therefore, a fluorescent device with a long lifespan can be realized while more effectively preventing or reducing the reduction in efficiency of the organic light-emitting device.
[0148] In one or more embodiments,
[0149] (i) the fluorescent dopant may be a hole-trapping emitter, and the triplet exciton quenching layer may be disposed between the emission layer and the electron transport region; or
[0150] (ii) The fluorescent dopant may be an electron capture emitter, and the triplet exciton quenching layer may be disposed between the emission layer and the hole transport region.
[0151] As used herein, the term "hole capture emitter" may refer to a component having a HOMO energy level and a LUMO energy level higher than the HOMO energy level and the LUMO energy level of the host. As used herein, the term "electron capture emitter" may refer to a component having a HOMO energy level and a LUMO energy level lower than the HOMO energy level and the LUMO energy level of the host.
[0152] When the fluorescent dopant is a hole-trapping emitter, an exciton recombination region in the emission layer is formed close to a hole transport region in the organic layer. In this case, since the triplet exciton quenching layer is disposed between the emission layer and the electron transport region, the triplet exciton quenching layer does not quench singlet excitons, but instead selectively quenches triplet excitons. Therefore, a fluorescent device with a long lifespan can be realized while more effectively preventing or reducing the reduction in efficiency of the organic light-emitting device.
[0153] When the fluorescent dopant is an electron capture emitter, the exciton recombination region in the emission layer is formed close to the electron transport region in the organic layer. In this case, since the triplet exciton quenching layer is disposed between the emission layer and the hole transport region, the triplet exciton quenching layer does not quench singlet excitons, but instead selectively quenches triplet excitons. Therefore, a fluorescent device with a long life can be realized while more effectively preventing or reducing the reduction in efficiency of the organic light-emitting device.
[0154] The amount of the dopant in the emission layer may be in a range between about 0.01 parts by weight and about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.
[0155] The thickness of the emitter layer can be approximately To about In the range of, for example, about To about When the thickness of the emission layer is within this range, excellent light emitting characteristics can be obtained without significantly increasing the driving voltage.
[0156] In one embodiment, the triplet exciton quenching layer may include a triplet exciton quenching additive. 1 ) energy level is lower than the main body T 1 Energy-level materials act as triplet exciton quenching additives.
[0157] In one embodiment, the triplet exciton quenching additive may include heavy atoms.
[0158] In one or more embodiments, the triplet exciton quenching additive may include a halogen group heavy atom (heavy halogen atom).
[0159] For example, the triplet exciton quenching additive may include a Br atom or an I atom, but the embodiments of the present disclosure are not limited thereto.
[0160] In one or more embodiments, the triplet exciton quenching additive may include a heavy atom and may also include a T 1 Low energy level T 1For example, the triplet exciton quenching additive may include a Br atom or an I atom, and may also include, for example, a compound having a low T 1 Energy level of organic compounds, such as DPVBi, but the embodiments of the present disclosure are not limited thereto:
[0161] DPVBi
[0162]
[0163] In one embodiment, the amount of the triplet exciton quenching additive may be in a range of about 0.1 wt % to about 2 wt % in the triplet exciton quenching layer (eg, based on the total weight of the triplet exciton quenching layer).
[0164] In one embodiment, the triplet exciton quenching layer may further include a first matrix material.
[0165] In one embodiment, the first matrix material may be the same as the bulk in the emissive layer.
[0166] In one embodiment, when the triplet exciton quenching layer further includes a first matrix material, the amount of the first matrix material can be in a range of about 80 wt % to about 99.9 wt %, or about 95 wt % to about 99.9 wt %, or about 98 wt % to about 99.9 wt % in the triplet exciton quenching layer (e.g., based on the total weight of the triplet exciton quenching layer).
[0167] In one embodiment, the thickness of the triplet exciton quenching layer may be in the range of about 0.01 nm to about 2 nm. For example, the thickness of the triplet exciton quenching layer may be in the range of about 0.1 nm to about 1 nm, but the embodiments of the present disclosure are not limited thereto.
[0168] In one embodiment, the emission layer may emit blue fluorescence having a maximum emission wavelength of about 440 nm to about 490 nm (or a maximum emission wavelength of about 450 nm to about 490 nm).
[0169] In one embodiment, the ratio of the delayed fluorescent component to the total luminescent components emitted from the emission layer may be about 20% or less.
[0170] Triplet-triplet annihilation (TTA), triplet-polaron quenching (TPQ), etc. have been found as intrinsic causes for determining (or reducing) the lifetime of an organic light-emitting device. This is a phenomenon in which the material of a device is degraded by triplet excitons, which are excitons with a long lifetime.
[0171] Although the present disclosure should not be limited to a specific mechanism or theory, since the organic light-emitting device according to the present disclosure includes a triplet exciton quenching layer located between the emission layer and the electrode, the lifetime of the fluorescent device can be increased by quenching triplet excitons (which are excitons with a long lifetime).
[0172] In addition, since the triplet exciton quenching layer exists as a layer separated from the emission layer, the exciton recombination region can be separated from the triplet exciton quenching region. Therefore, since the triplet exciton quenching layer is included, the efficiency of the organic light-emitting device is not reduced, and the life of the organic light-emitting device is increased.
[0173] Subject in the emission layer
[0174] In one or more embodiments, the host may include a compound represented by Formula 301.
[0175] Formula 301
[0176] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .
[0177] In formula 301,
[0178] Ar 301 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0179] xb11 can be 1, 2 or 3,
[0180] L 301 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0181] xb1 can be an integer from 0 to 5.
[0182] R 301 It can be selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, 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 ),
[0183] xb21 can be an integer from 1 to 5,
[0184] Q 301 To Q 303 can be independently selected from C 1 -C 10 Alkyl, C 1-C 10 An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the embodiments of the present disclosure are not limited thereto.
[0185] In one embodiment, Ar in Formula 301 301 Can be selected from:
[0186] naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, peryl, phenanthrenyl, indenoanthryl, dibenzofuranyl, and dibenzothiophenyl; and
[0187] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -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 ) and -P(=O)(Q 31 )(Q 32 ) is at least one of naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, peryl, peryl, pentaphenyl, indenoanthryl, dibenzofuranyl and dibenzothiophenyl,
[0188] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the embodiments of the present disclosure are not limited thereto.
[0189] When xb11 in Formula 301 is two or more, two or more Ar 301 Connection can be made via a single button.
[0190] In one or more embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or Formula 301-2:
[0191] Formula 301-1
[0192]
[0193] Formula 301-2
[0194]
[0195] In Formula 301-1 and Formula 301-2,
[0196] A 301 To A 304 can be independently selected from phenyl, naphthyl, phenanthrenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyridyl, pyrimidyl, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, indolyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, furanyl, benzofuranyl, dibenzofuranyl, naphthofuranyl, benzonaphthofuranyl, dinaphthofuranyl, thienyl, benzothienyl, dibenzothienyl, naphthiothienyl, benzonaphthothienyl and dinaphthothienyl,
[0197] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304 ],
[0198] R 311 To R 314 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -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 ) and -P(=O)(Q 31 )(Q 32 ),
[0199] xb22 and xb23 can each independently be 0, 1 or 2,
[0200] L 301 、xb1、R 301 and Q 31 To Q 33 may all independently be the same as described above,
[0201] L 302 To L 304 can be independently combined with L 301 Same as described,
[0202] xb2 to xb4 may each independently be the same as described in conjunction with xb1,
[0203] R 302 To R 304 can be independently combined with R 301 Same as described.
[0204] For example, in Formula 301, Formula 301-1, and Formula 301-2, L 301 To L 304 Can be independently selected from:
[0205] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene, and azacarbazolylene; and
[0206] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridyl azine, pyrimidinyl, pyridazinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -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 ) and -P(=O)(Q 31 )(Q 32 ) is at least one of phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene, yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene , pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene and azacarbazolylene,
[0207] Q 31 To Q 33 may all independently be the same as described above.
[0208] In one embodiment, in Formula 301, Formula 301-1 and Formula 301-2, R 301 To R 304 Can be independently selected from:
[0209] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0210] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridyl azine, pyrimidinyl, pyridazinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl,
[0211] Q 31 To Q 33 may all independently be the same as described above.
[0212] In one or more embodiments, the host may include an alkaline earth metal complex. For example, the host may be selected from a Be complex (eg, compound H55), a Mg complex, and a Zn complex.
[0213] In one embodiment, the host may include a compound represented by Formula 301-3:
[0214] Formula 301-3
[0215]
[0216] In formula 301-3,
[0217] A 301 To A 304 can be independently selected from phenyl, naphthyl, phenanthrenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyridyl, pyrimidyl, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, indolyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, furanyl, benzofuranyl, dibenzofuranyl, naphthofuranyl, benzonaphthofuranyl, dinaphthofuranyl, thienyl, benzothienyl, dibenzothienyl, naphthiothienyl, benzonaphthothienyl and dinaphthothienyl,
[0218] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304 ],
[0219] R 311 To R 314 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -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 ) and -P(=O)(Q 31 )(Q 32 ),
[0220] xb22 and xb23 can each independently be 0, 1 or 2,
[0221] L 301 To L 305 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0222] xb1 to xb4 may each independently be an integer from 1 to 5,
[0223] xb5 can be an integer from 0 to 5.
[0224] R 301 To R 304 can be independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, 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 ),
[0225] Q 31 To Q 33 and Q 301 To Q 303 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0226] The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), 3,3'-di(9H-carbazol-9-yl)biphenyl (mCBP), and compounds H1 to H55, but embodiments of the present disclosure are not limited thereto:
[0227]
[0228]
[0229]
[0230] Fluorescent dopants in the emitting layer
[0231] The fluorescent dopant may include an arylamine compound or a styrylamine compound.
[0232] The fluorescent dopant may include a compound represented by Formula 501:
[0233] Formula 501
[0234]
[0235] In formula 501,
[0236] Ar 501 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0237] L 501 To L 503 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0238] xd1 to xd3 may each independently be an integer from 0 to 3,
[0239] R 501 and R 502 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
[0240] xd4 can be an integer from 1 to 6.
[0241] In one embodiment, Ar in Formula 501 501 Can be selected from:
[0242] naphthyl, heptathenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, phenanthrenyl, perylenyl, pentaphenanthrenyl, indenoanthryl, and indenophenanthrenyl; and
[0243] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20at least one of an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group, a naphthyl group, a heptathenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a benzo[9,10]phenanthrenyl group, a pyrenyl group, The following examples include 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33,
[0244] In one or more embodiments, L in Formula 501 501 To L 503 Can be independently selected from:
[0245] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, ...
[0246] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, a phenylene radical, a naphthylene radical, a fluorenyl radical, a spirobifluorenyl radical, a benzofluorenyl radical, a dibenzofluorenyl radical, a phenanthrenyl radical, an anthracene radical, a fluoranthenyl radical, a benzo[9,10]phenanthrenyl radical, a pyrenyl radical, a fluorenyl radical, a phenanthren ... The compounds include phenylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothiophenylene, and pyridylene.
[0247] In one or more embodiments, in Formula 501, R 501 and R 502 Can be independently selected from:
[0248] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridyl; and
[0249] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl and -Si(Q 31 )(Q 32 )(Q 33 ) is at least one of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, benzothiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, ...
[0250] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0251] In one or more embodiments, xd4 in equation 501 may be 2, but embodiments of the present disclosure are not limited thereto.
[0252] For example, the fluorescent dopant may be selected from Compound FD1 to Compound FD22:
[0253]
[0254]
[0255] In one or more embodiments, the fluorescent dopant may be selected from the following compounds, but the embodiments of the present disclosure are not limited thereto:
[0256]
[0257] Electron transport region in the organic layer 150
[0258] The electron transport region may have: i) a single layer structure including a single layer including a single material; ii) a single layer structure including a single layer including a plurality of different materials; or iii) a multilayer structure having a plurality of layers including a plurality of different materials.
[0259] The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but the embodiments of the present disclosure are not limited thereto.
[0260] For example, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein for each structure, the constituent layers are sequentially stacked from the emission layer. However, the embodiment of the structure of the electron transport region is not limited thereto.
[0261] The electron transport region (eg, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one π electron-depleted nitrogen-containing ring.
[0262] As used herein, the term "π-electron-poor nitrogen-containing ring" may refer to a C 1 -C 60 Heterocyclic group.
[0263] For example, the "π-electron-poor nitrogen-containing ring" may be i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' portion, ii) a heteropolycyclic group in which two or more 5- to 7-membered heteromonocyclic groups each having at least one *-N=*' portion are condensed with each other, or iii) at least one 5- to 7-membered heteromonocyclic group each having at least one *-N=*' portion and at least one C 5 -C 60 A carbocyclic condensed heteropolycyclic group.
[0264] Examples of π-electron-poor nitrogen-containing rings include, but are not limited to, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine and azacarbazole.
[0265] For example, the electron transport region may include a compound represented by Formula 601:
[0266] Formula 601
[0267] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0268] In formula 601,
[0269] Ar 601 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0270] xe11 can be 1, 2 or 3,
[0271] L 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0272] xe1 can be an integer from 0 to 5,
[0273] R 601 Can be selected from substituted or unsubstituted C 3 -C10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),
[0274] Q 601 To Q 603 can be independently C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, terphenyl or naphthyl,
[0275] xe21 can be an integer from 1 to 5.
[0276] In one embodiment, the Ar of the number of xe11 601 and xe21 number of R 601 At least one selected from may include a π-electron-poor nitrogen-containing ring.
[0277] In one embodiment, in Formula 601, Ar 601 Can be selected from:
[0278] Phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, phenanthrenyl, phenanthrenyl, phenanthrenyl, phenanthryl, phenanthroline, phenazinyl, phenanthryl ...
[0279] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, phenanthracene, phenanthrenyl, phenanthrenyl, phenanthryl, phenanthroline, phenazine, phenanthryl ...
[0280] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0281] When xe11 in Formula 601 is two or greater, two or more Ar 601 Can connect via one-touch.
[0282] In one or more embodiments, Ar in Formula 601 601 It may be anthracene.
[0283] In one or more embodiments, the compound represented by Formula 601 can be represented by Formula 601-1:
[0284] Formula 601-1
[0285]
[0286] In formula 601-1,
[0287] X 614 Can be N or C (R 614 ), X 615 Can be N or C (R 615 ), X 616 Can be N or C (R 616 ), where, from X 614 To X 616 At least one of the selected ones may be N,
[0288] L 611 To L 613 can be independently combined with L 601 Same as described,
[0289] xe611 to xe613 can each independently be the same as described in conjunction with xe1,
[0290] R 611 To R 613 can be independently combined with R 601 Same as described,
[0291] R 614 To R 616 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0292] In one embodiment, L in equation 601 and equation 601-1 601 and L 611 To L 613 Can be independently selected from:
[0293] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene, and azacarbazolylene; and
[0294] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalide the phenylene radical of at least one of oxazinyl, naphthidinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthrylenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene , pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene and azacarbazolylene,
[0295] However, the embodiments of the present disclosure are not limited thereto.
[0296] In one or more embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 may each independently be 0, 1, or 2.
[0297] In one or more embodiments, in Formula 601 and Formula 601-1, R 601 and R 611 To R 613 Can be independently selected from:
[0298] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl;
[0299] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a benzo[9,10]phenanthrenyl group, a pyrenyl group, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0300] -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),
[0301] Q 601 and Q 602 may all independently be the same as described above.
[0302] The electron transport region may include at least one compound selected from compound ET1 to compound ET36, but the embodiments of the present disclosure are not limited thereto:
[0303]
[0304]
[0305]
[0306] In one or more embodiments, the electron transport region may include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 At least one compound selected from the group consisting of BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ) and NTAZ:
[0307]
[0308] The thickness of the buffer layer, hole blocking layer or electron control layer can be about To about In the range of, for example, about To about When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, the hole blocking layer may have excellent hole blocking properties and / or the electron control layer may have excellent electron control properties without significantly increasing the driving voltage.
[0309] In one embodiment, the electron transport region may include a hole blocking layer, which may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0310] The thickness of the electron transport layer can be about To about In the range of, for example, about To about When the thickness of the electron transport layer is within the range described above, the electron transport layer may have appropriate or satisfactory electron transport characteristics without significantly increasing the driving voltage.
[0311] The electron transport region (eg, an electron transport layer in the electron transport region) may further include a material including a metal in addition to the materials described above.
[0312] The material containing metal may include at least one selected from alkali metal complexes and alkaline earth metal complexes. The alkali metal complex may include metal ions selected from Li ions, Na ions, K ions, Rb ions and Cs ions, and the alkaline earth metal complex may include metal ions selected from Be ions, Mg ions, Ca ions, Sr ions and Ba ions. The ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.
[0313] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium quinolate, LiQ) or compound ET-D2:
[0314]
[0315] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 190. The electron injection layer may directly contact the second electrode 190.
[0316] The electron injection layer may have: i) a single layer structure including a single layer including a single material; ii) a single layer structure including a single layer including a plurality of different materials; or iii) a multilayer structure having a plurality of layers including a plurality of different materials.
[0317] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0318] The alkali metal may be selected from Li, Na, K, Rb and Cs. In one embodiment, the alkali metal may be Li, Na or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but the embodiments of the present disclosure are not limited thereto.
[0319] The alkaline earth metal may be selected from Mg, Ca, Sr and Ba.
[0320] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb and Gd.
[0321] The alkali metal compound, alkaline earth metal compound and rare earth metal compound may be selected from oxides and halides (eg, fluorides, chlorides, bromides or iodides) of alkali metals, alkaline earth metals and rare earth metals.
[0322] The alkali metal compound may be selected from alkali metal oxides (such as Li 2 O, Cs 2 O or K 2 O) and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI or KI). In one embodiment, the alkali metal compound may be selected from LiF, Li 2 O, NaF, LiI, NaI, CsI and KI, but the embodiments of the present disclosure are not limited thereto.
[0323] The alkaline earth metal compound may be selected from alkaline earth metal oxides such as BaO, SrO, CaO, Ba x Sr 1-x O (0 < x < 1) or Ba x Ca 1-x O (0 < x < 1). In one embodiment, the alkaline earth metal compound may be selected from BaO, SrO and CaO, but the embodiments of the present disclosure are not limited thereto.
[0324] The rare earth metal compound may be selected from YbF 3 , ScF 3 , Sc 2 O 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 and TbF 3 . In one embodiment, the rare earth metal compound may be selected from YbF 3 , ScF 3 , TbF 3 , YbI 3 , ScI 3 and TbI 3 , but the embodiments of the present disclosure are not limited thereto.
[0325] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may include ions of alkali metals, alkaline earth metals and rare earth metals as described above, and the ligands coordinated with the metal ions of the alkali metal complex, alkaline earth metal complex or rare earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.
[0326] The electron injection layer may include alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof (e.g., consisting of the above materials) as described above. In one or more embodiments, the electron injection layer may also include organic materials. When the electron injection layer also includes organic materials, alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix including an organic material.
[0327] The thickness of the electron injection layer can be about To about In the range of, for example, about To about When the thickness of the electron injection layer is within the range described above, the electron injection layer may have appropriate or satisfactory electron injection characteristics without significantly increasing the driving voltage.
[0328] The second electrode 190
[0329] The second electrode 190 may be disposed on the organic layer 150 having such a structure. The second electrode 190 may be a cathode as an electron injection electrode, and in this regard, a material for forming the second electrode 190 may be selected from metals, alloys, conductive compounds, and combinations thereof having a relatively low work function.
[0330] The second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, and IZO, but the embodiments of the present disclosure are not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0331] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.
[0332] In the above, reference has been made to Figure 1 An organic light emitting device is described, but embodiments of the present disclosure are not limited thereto.
[0333] A layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region can be formed in a specific region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser induced thermal imaging.
[0334] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, for example, the deposition temperature may be about 100° C. to about 500° C., about 10 -8 Up to about 10 -3 Torr vacuum and approx. / second to approximately The vacuum deposition was performed at a deposition rate of 2000 Å / s.
[0335] When a layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region are formed by spin coating, spin coating can be performed at a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80°C to about 200°C by taking into account the materials to be included in the layer to be formed and the structure of the layer to be formed.
[0336] The organic light-emitting device according to the embodiment of the present disclosure can be applied to a display device. The display device may include, for example, a thin film transistor having a source electrode, a drain electrode and an active layer, and one of the source electrode and the drain electrode of the thin film transistor may be electrically connected to the first electrode 110 of the organic light-emitting device according to the embodiment of the present disclosure.
[0337] [General definitions of some substituents]
[0338] As used herein, the term “C 1 -C 60 "Alkyl" refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl. As used herein, the term "C 1 -C 60 "Alkylene" refers to a group having a C 1 -C 60 The structure of the alkyl group is basically the same as the divalent group of the structure.
[0339] As used herein, the term “C 2 -C 60 "Alkenyl" refers to 2 -C 60 Alkyl refers to a hydrocarbon group having at least one carbon-carbon double bond at the main chain (e.g., in the middle) or at the end, examples of which include ethenyl, propenyl, and butenyl. As used herein, the term “C 2 -C 60 "Alkenylene" refers to a 2 -C 60 The structure of the alkenyl group is a divalent group of substantially the same structure.
[0340] As used herein, the term “C2 -C 60 "Alkynyl" refers to a C 2 -C 60 An alkyl group is a hydrocarbon group having at least one carbon-carbon triple bond at the main chain (e.g., in the middle) or at the end, examples of which include ethynyl and propynyl. As used herein, the term “C 2 -C 60 "Alkyne" refers to a group having a C 2 -C 60 The structure of the alkynyl group is a divalent group of substantially the same structure.
[0341] As used herein, the term “C 1 -C 60 "Alkoxy" refers to -OA 101 (Among them, A 101 C 1 -C 60 An alkyl group is a monovalent group represented by an alkyl group, examples of which include a methoxy group, an ethoxy group and an isopropoxy group.
[0342] As used herein, the term “C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, examples of which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. As used herein, the term "C 3 -C 10 "Cycloalkylene" refers to a cycloalkylene group having a 3 -C 10 The structure of the cycloalkyl group is substantially the same as that of a divalent group.
[0343] As used herein, the term “C 1 -C 10 "Heterocycloalkyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as ring atoms and 1 to 10 carbon atoms, examples of which include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and tetrahydrothienyl. As used herein, the term "C 1 -C 10 "Heterocycloalkylene" refers to a group having a C 1 -C 10 The structure of the heterocycloalkyl group is substantially the same as that of a divalent group.
[0344] As used herein, the term “C 3 -C 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not having aromaticity (e.g., the entire group and / or molecule does not have aromaticity), examples of which include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C 3-C 10 "Cycloalkenylene" refers to a 3 -C 10 The structure of the cycloalkenyl group is a divalent group of substantially the same structure.
[0345] As used herein, the term “C 1 -C 10 The term "heterocycloalkenyl group" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as ring atoms, 1 to 10 carbon atoms and at least one double bond in its ring. 1 -C 10 Non-limiting examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" refers to a 1 -C 10 The structure of the heterocycloalkenyl group is a divalent group of substantially the same structure.
[0346] As used herein, the term “C 6 -C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. 6 -C 60 The arylene group refers to a divalent group having a carbocyclic aromatic system including 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and When C 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the rings may be fused to each other (eg, bonded together).
[0347] As used herein, the term “C 1 -C 60 "Heteroaryl" refers to a monovalent group having a carbocyclic aromatic system having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom in addition to 1 to 60 carbon atoms. As used herein, the term "C 1 -C 60 The term "heteroarylene" refers to a divalent group having a carbocyclic aromatic system having at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom in addition to 1 to 60 carbon atoms. 1 -C 60Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene group includes two or more rings, the rings may be condensed with each other.
[0348] As used herein, the term “C 6 -C 60 "Aryloxy" refers to -OA 102 (Among them, A 102 C 6 -C 60 Aryl), as used herein, the term "C 6 -C 60 "Arylthio" refers to -SA 103 (Among them, A 103 C 6 -C 60 aryl).
[0349] As used herein, the term "monovalent non-aromatic condensed polycyclic group" refers to a monovalent group having two or more rings condensed to each other (e.g., bound together), only carbon atoms (e.g., having 8 to 60 carbon atoms) as ring atoms, and not having aromaticity in its entire molecular structure (e.g., the entire molecule does not have aromaticity). An example of a monovalent non-aromatic condensed polycyclic group is a fluorenyl group. As used herein, the term "divalent non-aromatic condensed polycyclic group" refers to a divalent group having a structure substantially the same as that of a monovalent non-aromatic condensed polycyclic group.
[0350] As used herein, the term "monovalent non-aromatic condensed heteropolycyclic group" refers to a monovalent group having two or more rings condensed with each other, having at least one heteroatom selected from N, O, Si, P and S other than carbon atoms (e.g., having 1 to 60 carbon atoms) as ring-forming atoms, and not having aromaticity in its entire molecular structure (e.g., the entire molecule does not have aromaticity). An example of a monovalent non-aromatic condensed heteropolycyclic group is a carbazolyl group. As used herein, the term "divalent non-aromatic condensed heteropolycyclic group" refers to a divalent group having a structure substantially the same as that of a monovalent non-aromatic condensed heteropolycyclic group.
[0351] As used herein, the term “C 5 -C 60 "Carbocyclic group" refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms, wherein the ring atoms are only carbon atoms. 5 -C 60 The carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. 5 -C 60The carbocyclic group can be a ring (such as benzene), a monovalent group (such as phenyl) or a divalent group (such as phenylene). In one or more embodiments, the carbonyl group is connected to the carbonyl group. 5 -C 60 The number of substituents of the carbocyclic group, C 5 -C 60 The carbocyclic group may be a trivalent group or a tetravalent group.
[0352] As used herein, the term “C 1 -C 60 "Heterocyclic group" refers to a 5 -C 60 The structure of the carbocyclic group is substantially the same as that of the group except that as a ring-constituting atom, in addition to carbon (the number of carbon atoms may be in the range of 1 to 60), at least one hetero atom selected from N, O, Si, P and S is used.
[0353] Substituted C 5 -C 60 Carbocyclic, substituted C 1 -C 60 Heterocyclic, substituted C 3 -C 10 Cycloalkylene, substituted C 1 -C 10 Heterocycloalkylene, substituted C 3 -C 10 Cycloalkenylene, substituted C 1 -C 10 Heterocycloalkenylene, substituted C 6 -C 60 Arylene, substituted C 1 -C 60 Heteroarylene, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
[0354] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0355] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, 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 ) and -P(=O)(Q 11 )(Q 12 ) of at least one of C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C60 Alkynyl and C 1 -C 60 Alkoxy;
[0356] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;
[0357] are substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, 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 ) and -P(=O)(Q 21 )(Q 22 ) of at least one of C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0358] -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 ) and -P(=O)(Q 31 )(Q 32 ),
[0359] Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group and a terphenyl group.
[0360] As used herein, the term "Ph" means phenyl, as used herein, the term "Me" means methyl, as used herein, the term "Et" means ethyl, as used herein, the term "ter-Bu" or "Bu" means phenyl. t " represents a tert-butyl group, and as used herein, the term "OMe" represents a methoxy group.
[0361] As used herein, the term "biphenyl" refers to a "phenyl group substituted with a phenyl group". 6 -C 60 "substituted phenyl" having "aryl" as a substituent.
[0362] As used herein, the term "terphenyl" refers to a phenyl group substituted with a biphenyl group. A "terphenyl" is a phenyl group substituted with a C 6 -C 60 Aryl C 6 -C 60 "phenyl" having "aryl" as a substituent.
[0363] Unless otherwise defined, * and *' as used herein refer to the binding sites to adjacent atoms in the corresponding formula.
[0364] Hereinafter, the compound according to the embodiment and the organic light emitting device according to the embodiment will be described in more detail with reference to examples. The expression "using B instead of A" used in describing the examples means using the same (eg, substantially the same) molar equivalent of B instead of the molar equivalent of A.
[0365] Example
[0366] Example 1
[0367] The ITO glass substrate was cut into a size of 50 mm × 50 mm × 0.5 mm, ultrasonically treated with isopropyl alcohol and pure water for 10 minutes each, and then cleaned by exposing to ultraviolet light and ozone for 10 minutes. Then, the ITO glass substrate was provided to a vacuum deposition device. NPB was vacuum deposited on the ITO glass substrate to form a A hole injection layer having a thickness of , and a hole transport material mCP is vacuum deposited on the hole injection layer to form a The compound DSA-Ph (dopant) and mCBP (host) were co-deposited on the hole transport layer at a weight ratio of 5:95 to form a Then, a triplet exciton quenching layer in which iodine as a triplet exciton quenching additive is contained in an amount of 0.5 wt % (based on the total weight of the triplet exciton quenching layer) is formed on the emission layer to a thickness of 1 nm. Then, TPBi is deposited on the triplet exciton quenching layer to form An electron transport layer having a thickness of , and Al is vacuum deposited on the electron transport layer to form a An Al electrode with a thickness of is formed, thereby completing the manufacture of the organic light-emitting device.
[0368] mCBP
[0369]
[0370] DSA-Ph
[0371]
[0372] TPB
[0373]
[0374] Example 2
[0375] An organic light emitting device was manufactured in substantially the same manner as in Example 1, except that bromine was used instead of iodine.
[0376] Comparative Example 1
[0377] An organic light emitting device was manufactured in substantially the same manner as in Example 1, except that the triplet exciton quenching layer was not formed.
[0378] Comparative Example 2
[0379] An organic light emitting device was manufactured in substantially the same manner as in Example 1, except that the triplet exciton quenching layer was not formed and iodine was included in an amount of 0.5 wt % (based on the total weight of the emission layer) in forming the emission layer.
[0380] Evaluation Example 1
[0381] The luminance (cd / m2) of the organic light emitting devices manufactured according to Examples 1 and 2 and Comparative Examples 1 and 2 was measured by using Keithley SMU 236, luminance meter PR650, oscilloscope 54810A, and Hammamtsu PMT. 2 )(Current density is 10 mA / cm 2), efficiency (cd / A), 97% lifetime and delayed fluorescence (DF) component, and the results are shown in Table 1.
[0382] The results obtained by measuring the lifetime of the organic light emitting devices manufactured according to Examples 1 and 2 and Comparative Example 1 are shown in Figure 4 and the results obtained by measuring the DF component using transient electroluminescence (EL) are shown in Figure 5 middle.
[0383] Table 1
[0384]
[0385] Refer to Table 1 and Figure 4 It is demonstrated that, compared with the efficiency and lifespan of the organic light emitting device of Comparative Example 1, the organic light emitting devices of Examples 1 and 2 achieve similar levels of efficiency and have excellent lifespans of about three times or more.
[0386] In addition, referring to Table 1, it is confirmed that, compared with the efficiency of the organic light emitting device of Comparative Example 2, the organic light emitting devices of Examples 1 and 2 have excellent efficiency.
[0387] In addition, refer to Figure 5 , it is demonstrated that the delayed triplet exciton component in the organic light-emitting devices of Examples 1 and 2 is significantly reduced than that in the organic light-emitting device of Comparative Example 1.
[0388] For example, the organic light emitting device according to the embodiment may exhibit excellent effects in terms of driving voltage, brightness, efficiency, and lifespan.
[0389] An organic light emitting device including a triplet exciton quenching layer may have a long lifetime.
[0390] It will be understood that, although the terms "first", "second", "third", etc. may be used herein to describe various elements, components, regions, layers and / or parts, these elements, components, regions, layers and / or parts should not be limited by these terms. These terms are used to distinguish one element, component, region, layer or part from another element, component, region, layer or part. Therefore, without departing from the spirit and scope of the present disclosure, the first element, component, region, layer or part described below may be named as the second element, component, region, layer or part.
[0391] For ease of explanation, spatially relative terms such as "under", "below", "below", "under", "above", "on", etc. may be used herein to describe the relationship of one element or feature to another element or feature as shown in the figure. It will be understood that in addition to the orientations depicted in the drawings, the spatially relative terms are intended to include different orientations of the device in use or operation. For example, if the device in the drawings is turned over, the elements described as "below" or "below" or "below" other elements or features will then be positioned as "above" the other elements or features. Therefore, the example terms "below" and "under" can include both above and below orientations. The device can be positioned otherwise (e.g., rotated 90 degrees or in other orientations), and the spatially relative descriptors used herein should be interpreted accordingly.
[0392] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. When an expression such as "at least one of..." follows a list of elements (elements), it modifies the entire list of elements (elements), rather than modifying the individual elements (elements) of the list.
[0393] As used herein, the terms "substantially", "approximately" and similar terms are used as approximate terms, rather than as terms of degree, and are intended to explain the inherent deviations in measurements or calculations that will be recognized by those of ordinary skill in the art. In addition, when describing embodiments of the present disclosure, the use of "may" refers to "one or more embodiments of the present disclosure." As used herein, the term "using" and variations thereof may be considered to be synonymous with the term "utilizing" and variations thereof, respectively. In addition, the term "exemplary" is intended to represent an example or illustration.
[0394] In addition, any numerical range stated herein is intended to include all sub-ranges of the same numerical precision included in the stated range. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between the stated minimum value 1.0 and the stated maximum value 10.0 (and including the minimum value 1.0 and the maximum value 10.0), that is, with a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical value limit stated herein is intended to include all lower numerical limits included therein, and any minimum numerical value limit stated in this specification is intended to include all higher numerical limits included therein. Therefore, the applicant reserves the right to modify this specification (including claims) to explicitly state any sub-range included in the scope explicitly stated herein.
[0395] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should generally be considered as available for other similar features or aspects in other embodiments.
[0396] Although one or more embodiments have been described with reference to the drawings, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the claims and their equivalents.
Claims
1. An organic light-emitting device, comprising: a first electrode; a second electrode, facing the first electrode; as well as an organic layer, located between the first electrode and the second electrode, and comprising an emission layer, a hole transport region between the first electrode and the emission layer, an electron transport region between the emission layer and the second electrode, and a triplet exciton quenching layer, wherein the triplet exciton quenching layer comprises a triplet exciton quenching additive, and the triplet exciton quenching additive comprises a heavy halogen atom, The triplet exciton quenching layer is located between the emission layer and the hole transport region, or between the emission layer and the electron transport region. wherein the emission layer comprises a host and a dopant, and the dopant comprises a fluorescent dopant, Wherein, the host comprises a compound represented by Formula 301-3: Formula 301-3 Among them, in formula 301-3, A 301 To A 304 are independently selected from phenyl, naphthyl, phenanthrenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyridyl, pyrimidyl, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, indolyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, furanyl, benzofuranyl, dibenzofuranyl, naphthofuranyl, benzonaphthofuranyl, dinaphthofuranyl, thienyl, benzothienyl, dibenzothienyl, naphthothienyl, benzonaphthothienyl and dinaphthothienyl, X 301 O, S or N-[(L 304 ) xb4 -R 304 ], R 311 To R 314 are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -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 ) and -P(=O)(Q 31 )(Q 32 ), xb22 and xb23 are independently 0, 1 or 2, L 301 To L 305 are independently selected from substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocycloalkylene, substituted or unsubstituted C3-C 10 Cycloalkenylene, substituted or unsubstituted C1-C 10 Heterocycloalkenylene, substituted or unsubstituted C6-C 60 Arylene, substituted or unsubstituted C1-C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group, xb1 to xb4 are each independently an integer from 1 to 5, xb5 is an integer from 0 to 5, R 301 To R 304 are independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, 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 ),and Q 31 To Q 33 and Q 301 To Q 303 are independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl, Wherein, the fluorescent dopant includes a compound represented by Formula 501: Formula 501 Wherein, in Formula 501, Ar 501 is substituted or unsubstituted C5-C 60 Carbocyclic or substituted or unsubstituted C1-C 60 Heterocyclic group, L 501 To L 503 are independently selected from substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocycloalkylene, substituted or unsubstituted C3-C 10 Cycloalkenylene, substituted or unsubstituted C1-C 10 Heterocycloalkenylene, substituted or unsubstituted C6-C 60 Arylene, substituted or unsubstituted C1-C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and 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 independently selected from substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and xd4 is an integer from 1 to 6.
2. The organic light emitting device according to claim 1, wherein: (i) the exciton recombination zone in the emissive layer is located at the interface between the emissive layer and the electron transport region, and the triplet exciton quenching layer is located between the emissive layer and the hole transport region; or (ii) the exciton recombination zone in the emissive layer is located at the interface between the emissive layer and the hole transporting region, and the triplet exciton quenching layer is located between the emissive layer and the electron transporting region.
3. The organic light emitting device according to claim 1, wherein: (i) the highest occupied molecular orbital energy level E of the host HH , the lowest unoccupied molecular orbital energy level E of the subject HL , the highest occupied molecular orbital energy level E of the fluorescent dopant DH and the lowest unoccupied molecular orbital energy level E of the fluorescent dopant DL Satisfy |E DH |>|E HH | and|E DL |>|E HL |, and The triplet exciton quenching layer is located between the emission layer and the electron transport region; or (ii) the highest occupied molecular orbital energy level E of the host HH , the lowest unoccupied molecular orbital energy level E of the host HL , the highest occupied molecular orbital energy level E of the fluorescent dopant DH and the lowest unoccupied molecular orbital energy level E of the fluorescent dopant DL Satisfy |E DH |<|E HH | and|E DL |<|E HL |, and The triplet exciton quenching layer is located between the emission layer and the hole transport region.
4. The organic light emitting device according to claim 1, wherein: (i) the fluorescent dopant is a hole-trapping emitter, and the triplet exciton quenching layer is located between the emissive layer and the electron transport region; or (ii) The fluorescent dopant is an electron capture emitter, and the triplet exciton quenching layer is located between the emission layer and the hole transport region.
5. The organic light emitting device according to claim 1, wherein: In the triplet exciton quenching layer, an amount of the triplet exciton quenching additive is in a range of 0.1 wt % to 2.0 wt %.
6. The organic light emitting device according to claim 1, wherein: The thickness of the triplet exciton quenching layer is in the range of 0.01 nm to 2 nm.
7. The organic light emitting device according to claim 1, wherein: The emission layer emits blue fluorescence having a maximum emission wavelength of 450 nm to 490 nm.
8. The organic light emitting device according to claim 1, wherein: The ratio of the delayed fluorescent component to the total luminescent components emitted from the emission layer is 20% or less.
9. The organic light emitting device according to claim 1, wherein: The host is selected from 4,4'-bis(N-carbazolyl)-1,1'-biphenyl, 1,3-di-9-carbazolylbenzene, 1,3,5-tri(carbazol-9-yl)benzene and 3,3'-di(9H-carbazol-9-yl)biphenyl.
10. The organic light emitting device according to claim 1, wherein: The fluorescent dopant is selected from the following compounds:
11. The organic light emitting device according to claim 10, wherein: The fluorescent dopant is selected from the following compounds:
12. The organic light emitting device according to claim 1, wherein: The hole transport region includes an electron blocking layer, and The electron blocking layer includes a p-dopant having a lowest unoccupied molecular orbital energy level of -3.5 eV or less.
13. The organic light emitting device according to claim 1, wherein: The electron transport region includes a hole blocking layer, and The hole blocking layer includes an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, or any combination thereof.
14. The organic light emitting device according to claim 13, wherein: The hole blocking layer includes an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex or any combination thereof.
15. A display device, comprising: A thin film transistor, comprising a source electrode, a drain electrode and an active layer; as well as The organic light-emitting device according to claim 1, The first electrode of the organic light emitting device is electrically coupled to one selected from the source electrode and the drain electrode of the thin film transistor.
Citation Information
Patent Citations
Organic electroluminescence device
US20120126208A1