Organic light emitting device and apparatus including the same
By employing a double-layer hole transport layer structure in OLED devices and utilizing a combination of specific compounds and dopants to optimize hole mobility, the problem of low hole transport layer mobility in existing OLED devices is solved, thereby improving luminous efficiency and blue light luminous efficiency.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- SAMSUNG DISPLAY CO LTD
- Filing Date
- 2021-04-07
- Publication Date
- 2026-08-04
AI Technical Summary
Existing OLED devices suffer from low hole transport layer mobility, which affects luminous efficiency.
A dual-layer hole transport layer structure is adopted, including a first hole transport layer and a second hole transport layer, which are composed of different hole transport compounds and p-type dopants, respectively. By combining specific compounds and dopants, a certain HOMO energy level relationship is satisfied to optimize hole mobility.
This improves the hole mobility of OLED devices, thereby enhancing luminous efficiency and performance, particularly in the blue light wavelength range.
Smart Images

Figure CN113497199B_ABST
Abstract
Description
[0001] This application claims priority and benefit to Korean Patent Application No. 10-2020-0042403, filed on April 7, 2020, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field
[0002] One or more aspects of embodiments of this disclosure relate to an organic light-emitting device and an apparatus including the organic light-emitting device. Background Technology
[0003] Organic light-emitting devices (OLEDs) are self-emitting devices that, compared to other prior art devices, have a wider viewing angle, higher contrast, shorter response time, and / or superior characteristics in terms of brightness, driving voltage, and / or response speed, and produce full-color images.
[0004] An example OLED includes a first electrode disposed on a substrate and a hole transport region, an emitter layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes supplied from the first electrode can move towards the emitter layer through the hole transport region, and electrons supplied from the second electrode can move towards the emitter layer through the electron transport region. Charge carriers (such as holes and electrons) can recombine in the emitter layer to generate excitons. These excitons can transition from an excited state to a ground state, thereby generating light. Summary of the Invention
[0005] One or more aspects of embodiments of this disclosure relate to an organic light-emitting device and an apparatus including the organic light-emitting device.
[0006] Additional aspects will be set forth in part in the description which follows, and will also be apparent in part from the description, or may be learned by practice of the disclosed embodiments given.
[0007] One or more exemplary embodiments of this disclosure provide an organic light-emitting device, the organic light-emitting device comprising:
[0008] A first electrode, a second electrode facing the first electrode, and an organic layer disposed between the first electrode and the second electrode.
[0009] The organic layer may include an emitter layer and a hole transport region disposed between the first electrode and the emitter layer.
[0010] The hole transport region may include a first hole transport layer and a second hole transport layer.
[0011] The first hole transport layer may include a first hole transport compound and a p-type dopant.
[0012] The second hole transport layer may include a second hole transport compound, and
[0013] The emitter layer may include the host compound represented by Formula 1 and the dopant compound represented by Formula 2:
[0014] Formula 1
[0015]
[0016] Formula 2
[0017]
[0018] Among them, in Equations 1 and 2,
[0019] L1 and L2 can both be independently selected from single-bonded, substituted, or unsubstituted C3-C bonds. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed heterocyclic groups,
[0020] a1 and a2 can both be independent integers from 0 to 5.
[0021] Ar1 and Ar2 can both be independently selected from 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 C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups.
[0022] Y1 and Y2 can both be independently selected from single bonds, -O-, -S-, and -C(R). 41 (R) 42 )-、-N(R 41 )-、-Si(R 41 (R) 42 )-, -C(=O)-, -S(=O)2-, -B(R 41 )-、-P(R 42- and -P(=O)(R 41 )-,
[0023] Y3 can be N, B, P, P (=O) or P (=S).
[0024] CY1 to CY3 can all be independently selected from C5-C. 60 Carbocyclic groups and C1-C 60 Heterocyclic group,
[0025] R1 to R8, R 10 R 20 R 30 R 41 and R 42 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, 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 C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic groups, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), and -P(=O)(Q1)(Q2),
[0026] From R 10 R 20 R 30 R 41 and R 42 The two or more substituents selected may optionally be connected to each other to form substituted or unsubstituted C5-C. 60 Carbocyclic group or substituted or unsubstituted C1-C60 Heterocyclic group,
[0027] b10, b20, and b30 can each be an integer from 1 to 8 independently.
[0028] Replacement C3-C 10 Cycloalkylene, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 aryl, substituted C1-C 60 Hybrid aryl, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heterocyclic group, substituted C5-C 60 Carbocyclic groups, substituted C1-C 60 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 heteroaryl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 At least one substituent selected from the following: heteroarylsulfonyl, substituted monovalent nonaromatic condensed polycyclic group, and substituted monovalent nonaromatic condensed heterocyclic group.
[0029] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy
[0030] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, and C3-C. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic 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 Choose at least one of the C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy
[0031] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, and monovalent non-aromatic condensed heterocyclic group.
[0032] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic 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 Choose at least one of the C3-C options. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic condensed heterocyclic, and
[0033] -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 ),
[0034] Among them, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60Heteroaryl, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, biphenyl and terphenyl.
[0035] One or more exemplary embodiments of this disclosure provide an apparatus including a thin-film transistor and the organic light-emitting device, the thin-film transistor including a source electrode, a drain electrode and an active layer, wherein a first electrode of the organic light-emitting device is electrically connected to one of the source electrode and the drain electrode of the thin-film transistor. Attached Figure Description
[0036] The above and other aspects, features, and advantages of certain embodiments disclosed will become more apparent from the following description taken in conjunction with the accompanying drawings, in which:
[0037] Figure 1 This is a schematic cross-sectional view of an embodiment of an organic light-emitting device;
[0038] Figure 2 This is a schematic cross-sectional view of an embodiment of an organic light-emitting device;
[0039] Figure 3 A schematic cross-sectional view of an embodiment of an organic light-emitting device; and
[0040] Figure 4 This is a schematic cross-sectional view of an embodiment of an organic light-emitting device. Detailed Implementation
[0041] Referring now to embodiments in more detail, examples of which are shown in the accompanying drawings, wherein the same reference numerals always denote the same elements and may not be repeated in their description. In this respect, the given embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, the embodiments are described below with reference to the accompanying drawings only to explain aspects of this description. As used herein, the term “and / or” includes any and all combinations of one or more of the associated listed items. Throughout this disclosure, the expression “at least one of a, b, and c” may refer to only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.
[0042] Because this disclosure can have various embodiments and can be modified in various ways, exemplary embodiments will be shown in the accompanying drawings and described in detail in the specific embodiments. The effects and features of this disclosure, as well as methods for implementing them, will be illustrated by referring to the described embodiments. However, this disclosure is not limited to the embodiments disclosed below and can be implemented in various suitable forms.
[0043] As used herein, unless the context clearly indicates otherwise, the singular forms “a,” “one,” and “the” are also intended to include the plural forms.
[0044] It will also be understood that the terms “comprising” and / or “including” as used herein indicate the presence of a stated feature or component, but do not exclude the presence or addition of one or more other features or components. Furthermore, when describing embodiments of this disclosure, the use of “may” refers to “one or more embodiments of this disclosure”.
[0045] It will be understood that when a layer, region, or component is referred to as being "on" or "to" another layer, region, or component, that layer, region, or component may be formed directly or indirectly on said other layer, region, or component. That is, for example, intermediate layers, regions, or components may exist. Conversely, when the term "directly" is used, there are no intermediate elements.
[0046] For ease of illustration, the dimensions of the elements in the accompanying drawings may be exaggerated. For example, because the dimensions and thicknesses of the components in the drawings are arbitrarily shown for ease of illustration, the following embodiments of this disclosure are not limited thereto.
[0047] An organic light-emitting device according to an embodiment of the present disclosure includes a first electrode, a second electrode facing the first electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer may include an emission layer and a hole transport region disposed between the first electrode and the emission layer.
[0048] The term "organic layer" as used herein can refer to, for example, a single layer or multiple layers within an organic layer between the first and second electrodes of an organic light-emitting device. The materials included in the "organic layer" are not limited to organic materials.
[0049] According to one embodiment, the first electrode can be an anode and the second electrode can be a cathode.
[0050] The hole transport region may include a first hole transport layer and a second hole transport layer. The first hole transport layer may include a first hole transport compound and a p-type dopant, and the second hole transport layer may include a second hole transport compound. The second hole transport layer may consist only of the second hole transport compound.
[0051] According to one embodiment, a first hole transport layer may be disposed on a first electrode, and an emitter layer may be disposed on a second hole transport layer.
[0052] According to one embodiment, the first electrode can directly contact the first hole transport layer. According to one embodiment, the first hole transport layer can directly contact the second hole transport layer.
[0053] In one embodiment, the hole transport region may further include a hole injection layer, an emission assist layer, an electron blocking layer, or any combination thereof.
[0054] The emitter layer may include a host compound represented by Formula 1 and a dopant compound represented by Formula 2. The emitter layer may also include only the host compound represented by Formula 1 and the dopant compound represented by Formula 2. The emitter layer may be composed of the host compound represented by Formula 1 and the dopant compound represented by Formula 2.
[0055] According to an embodiment, the amount of the host compound in the emitter layer can be greater than the amount of the dopant compound.
[0056] According to one embodiment, the emitting layer can emit blue light with a maximum emission wavelength of about 410 nm to about 490 nm.
[0057] According to an embodiment, the emitter layer may include doped regions and undoped regions; the doped regions may include a host compound and a dopant compound, and the undoped regions may include a host compound.
[0058] According to one embodiment, the organic layer may further include an electron transport region disposed between the emitter layer and the second electrode, the electron transport region including a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0059] According to one embodiment, the electron transport region may include a metallic material.
[0060] Figure 1 Description
[0061] Figure 1 This is a schematic cross-sectional view 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.
[0062] In the following text, we will combine Figure 1 The structure of the organic light-emitting device 10 according to the embodiments and the method of manufacturing the organic light-emitting device 10 are described.
[0063] First electrode 110
[0064] exist Figure 1 In this process, the substrate may be additionally disposed below the first electrode 110 and / or above the second electrode 190. The substrate may be a glass substrate and / or a plastic substrate, both of which possess excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and / or water resistance.
[0065] The first electrode 110 can be formed, for example, by depositing or sputtering a material for forming the first electrode 110 onto a substrate. When the first electrode 110 is an anode, the material used for the first electrode 110 can be selected from materials with high work function to facilitate hole injection.
[0066] The first electrode 110 can be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but the embodiments of this disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transparent electrode or a reflective electrode, the material used to form the first electrode 110 can 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 this disclosure are not limited thereto.
[0067] 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 to this.
[0068] Organic layer 150
[0069] An organic layer 150 is disposed on the first electrode 110.
[0070] The organic layer 150 may include an emitter layer and a hole transport region disposed between the first electrode 110 and the emitter layer.
[0071] In one embodiment, the organic layer 150 may further include an electron transport region between the emitter layer and the second electrode 190.
[0072] Hole transport region in organic layer 150
[0073] Each layer included in the hole transport region may have: i) a single-layer structure comprising a single material; ii) a single-layer structure comprising multiple different materials; or iii) a multi-layer structure comprising multiple layers comprising multiple different materials.
[0074] The hole transport region may include a first hole transport layer and a second hole transport layer.
[0075] The first hole transport layer may include a first hole transport compound and a p-type dopant, and the second hole transport layer may include a second hole transport compound. The second hole transport layer may consist only of the second hole transport compound.
[0076] In one embodiment, the highest occupied molecular orbital (HOMO) energy level of the first electrode (HOMO) EL1 ), the HOMO level of the first hole transport layer (HOMO HT1 ) and the HOMO level of the second hole transport layer (HOMO HT2 It can satisfy Formula 1:
[0077] Formula 1
[0078] |HOMO EL1 |<|HOMO HT1 |<|HOMO HT2 |
[0079] In one embodiment, the thickness of the first hole transport layer can be approximately to approximately For example, about to approximately
[0080] In one embodiment, the thickness of the second hole transport layer can be approximately to approximately For example, about to approximately
[0081] When the thickness of each of the first and second hole transport layers meets these ranges, the hole mobility inside the organic light-emitting device can be excellent, thus improving the luminous efficiency of the organic light-emitting device.
[0082] According to one embodiment, the first hole transport compound and the second hole transport compound may each be independently selected from the compound represented by formula 201 and the compound represented by formula 202:
[0083] Formula 201
[0084]
[0085] Formula 202
[0086]
[0087] In equations 201 and 202,
[0088] L 201 To L 204 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed heterocyclic groups,
[0089] L 205 It can be selected from *-O-*', *-S-*', *-N(Q) 201 )-*', substituted or unsubstituted C1-C 20 Alkylene, substituted or unsubstituted C2-C 20 alkenyl, substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed heterocyclic groups,
[0090] xa1 to xa4 can each be an independent integer from 0 to 3.
[0091] xa5 can be an integer from 1 to 10.
[0092] R 201 To R 204 and Q 201 Each can be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, 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 nonaromatic condensed polycyclic groups, and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, and
[0093] Both * and *' represent bonding sites with adjacent atoms.
[0094] For example, in equation 202, R 201 and R 202They can be optionally linked to each other via single bonds, dimethyl-methylene, or diphenyl-methylene, and R 203 and R 204 They can be optionally linked to each other via single bonds, dimethyl-methylene, or diphenyl-methylene.
[0095] In one embodiment, in equations 201 and 202,
[0096] L 201 To L 205 Each can be independently selected from:
[0097] Phenylidene, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptadienyl, adafenyl, acenaphthene, fluorene, spirodifluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenenyl, anthracene, fluorenyl, benzo[9,10]phenenyl, pyrene, phenylene alkyl, benzotetraphenyl, purylene, perylene, pentaphenylene, benzohexaphenylene, benzopentaphenylene, benzobenzyl, benzoylene, oleophylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoydinolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzothiopheneyl, and pyridylene; and
[0098] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 Alkyl phenyl, substituted -F phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, pyrene alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32The following are selected from at least one of the following: phenylene, cyclopentadienylene, indenylene, naphthylene, chamomilecycloylene, heptadienylene, adaninylene, fluoreneylene, spirodifluoreneylene, benzo[9,10]fluoreneylene, dibenzo[9,10]fluoreneylene, phenanthroline, anthraceneylene, fluoranthroline, benzo[9,10]phenanthroline, pyreneylene, etc. alkyl, tetraphenyl, arbutinyl, perylene, pentaphenyl, hexaphenyl, pentaphenyl, rubidinyl, benzoyl, oleophyl, thiopheneyl, furanyl, carbazolyl, indoleyl, isoydinolyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, and pyridylyl.
[0099] Among them, Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0100] In one or more embodiments, xa1 to xa4 can each be independently 0, 1 or 2.
[0101] In one or more embodiments, xa5 can be 1, 2, 3 or 4.
[0102] In one or more embodiments, R 201 To R 204 and Q 201 All of these can be independently selected from phenyl, biphenyl, terphenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, phenanthyl, anthraceneyl, fluoranthyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoydinoleyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenyl, and pyridyl; and
[0103] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10Alkyl phenyl, substituted -F phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, pyrene alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, -Si(Q) 31 (Q) 32 (Q) 33 ) and -N(Q 31 (Q) 32 The following are selected from at least one of the following: phenyl, biphenyl, terphenyl, cyclopentadienyl, indole, naphthyl, chamomilecycloyl, heptalenyl, indoleyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, pyrene, alkyl, tetraphenyl, francyl, perylene, pentylenetyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiopheneyl, and pyridyl.
[0104] Among them, Q 31 To Q 33 They can all be independently identical to those described above.
[0105] In one or more embodiments, R from formula 201 201 To R 203 At least one of the selected items can be independently selected from:
[0106] Fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl and dibenzothiopheneyl; and
[0107] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 The alkyl group of phenyl, the phenyl group substituted with -F, naphthyl, fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl and dibenzothiopheneyl are selected from at least one of the following: fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl and dibenzothiopheneyl.
[0108] However, the embodiments disclosed herein are not limited thereto.
[0109] In one or more embodiments, in formula 202, i)R 201 and R 202 They can be connected to each other via a single key, and / or ii)R 203 and R 204 They can be connected to each other via a single key.
[0110] In one or more embodiments, R in formula 202 201 To R 204 At least one of them can be selected from:
[0111] Carbazolyl; and
[0112] Substitutions include deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 The carbazoyl group selected from at least one of the following: alkyl phenyl, phenyl substituted with -F, naphthyl, fluorenyl, spirodifluorenyl, carbazoyl, dibenzofuranyl, and dibenzothiopheneyl.
[0113] However, the embodiments disclosed herein are not limited thereto.
[0114] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A:
[0115] Formula 201A
[0116]
[0117] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A(1), but the embodiments of this disclosure are not limited thereto:
[0118] Formula 201A(1)
[0119]
[0120] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A-1, but the embodiments of this disclosure are not limited thereto:
[0121] Formula 201A-1
[0122]
[0123] In one or more embodiments, the compound represented by formula 202 can be represented by formula 202A:
[0124] Formula 202A
[0125]
[0126] In one or more embodiments, the compound represented by formula 202 can be represented by formula 202A-1:
[0127] Formula 202A-1
[0128]
[0129] In Equations 201A, 201A(1), 201A-1, 202A, and 202A-1,
[0130] L 201 To L 203 xa1 to xa3, xa5 and R 202 To R 204 Each can be independently identical to the one described above.
[0131] R 211 and R 212 They can all independently bind with R 203 The descriptions are the same, and
[0132] R 213 To R 217 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 Alkyl phenyl, substituted -F phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indaneyl, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthryl, dibenzo[9,10]fluorenyl, pyrene alkyl, tetraphenyl, furanyl, perylene, pentyranyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, leucophenyl, thiophenyl, furanyl, carbazoyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, dibenzothiophenyl, and pyridyl.
[0133] In one embodiment, the p-type dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of -3.5 eV or less.
[0134] In one embodiment, the p-type dopant may include at least one selected from quinone derivatives, metal oxides, and cyano-containing compounds. For example, the p-type dopant may include a cyano-containing compound.
[0135] In one embodiment, the p-type dopant may include at least one selected from the following compounds:
[0136] Quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl (F4-TCNQ);
[0137] Metal oxides, such as tungsten oxide or molybdenum oxide;
[0138] 1,4,5,8,9,12-hexaazabenzophenanthrene-hexanitrile (HAT-CN); and
[0139] The compound represented by formula 221,
[0140] However, the embodiments disclosed herein are not limited thereto:
[0141]
[0142] Equation 221
[0143]
[0144] In Equation 221,
[0145] R 221 To R 223 Each can be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, and from R 221 To R 223 At least one of the selected groups may have a C1-C group substituted with cyano, -F, -Cl, -Br, -I, or -F. 20 Alkyl groups, C1-C substituted with -Cl 20 Alkyl groups, C1-C substituted with -Br 20 Alkyl groups and substituted C1-C groups with -I 20 At least one substituent selected from alkyl groups.
[0146] In one embodiment, the hole transport region may include m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4”-tris(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), or combinations thereof.
[0147]
[0148]
[0149] In one embodiment, the hole transport region may include at least one compound selected from compounds HT1 to HT39, but the compounds to be included in the hole transport region are not limited thereto:
[0150]
[0151]
[0152]
[0153]
[0154] In addition to these materials, the hole transport region may also include charge-generating materials to improve conductivity. The charge-generating materials may be uniformly or non-uniformly dispersed within the hole transport region.
[0155] In one embodiment, the hole transport region may include at least one layer selected from the hole injection layer (HIL), the emission assist layer, and the electron blocking layer (EBL).
[0156] For example, the hole transport region can have a single-layer structure or a multi-layer structure. The single-layer structure includes a variety of different materials. The multi-layer structure has a hole injection layer / first hole transport layer / second hole transport layer structure, a hole injection layer / first hole transport layer / second hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / first hole transport layer / second hole transport layer / electron blocking layer structure. The constituent layers of each structure are stacked sequentially from the first electrode 110 in the order stated therein, but the structure of the hole transport region is not limited to this.
[0157] The thickness of the hole transport region can be approximately to approximately For example, for about to approximately When the hole transport region includes at least one selected from the hole injection layer and the hole transport layer, the thickness of the hole injection layer can be approximately to approximately For example, for about to approximately The thickness of the hole transport layer can be approximately to approximately For example, for about to approximately When the hole transport region, hole injection layer, and hole transport layer thickness are within these ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0158] The emission assist layer can improve the luminous efficiency of the device by compensating for the optical resonant distance of the wavelength of light emitted by the emission layer, and the electron blocking layer can block or reduce the inflow of electrons from the electron transport region. Both the emission assist layer and the electron blocking layer can comprise the materials described above.
[0159] Emission layer in organic layer 150
[0160] The host and dopants in the emitter layer
[0161] The emitter layer may include the host compound represented by Formula 1 and the dopant compound represented by Formula 2:
[0162] Formula 1
[0163]
[0164] Formula 2
[0165]
[0166] In Equation 1, L1 and L2 can both be independently selected from single-bonded, substituted, or unsubstituted C3-C bonds. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent nonaromatic condensed polycyclic groups and substituted or unsubstituted divalent nonaromatic condensed heterocyclic groups.
[0167] In one embodiment, L1 and L2 can both be independently selected from:
[0168] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenylanethyl, benzo[9,10]phenanthrene, pyrene, phenanthrene Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrenediyl, acridineyl, phenanthrene-rheinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl; and
[0169] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazole, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridinyl Azinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, 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 The following are selected from at least one of the following: phenylene, naphthylene, fluorene, spirodifluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenanthrene, anthracene, fluoranthracene, benzo[9,10]phenanthrene, pyrene, etc. Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthreneridinyl, acridineyl, phenanthrene-pyridinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl,
[0170] Among them, Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, and substituted with C1-C 10 Alkyl groups including phenyl, biphenyl, terphenyl, and naphthyl.
[0171] In one embodiment, L1 and L2 may each be independently a single bond or a group represented by one of Formulas 3-1 to 3-36:
[0172]
[0173]
[0174] Among them, in equations 3-1 to 3-36,
[0175] Y 11 It can be *-O-*', *-S-*', or *-N(Z5)-*'.
[0176] Z1 to Z5 can all be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, dibenzothiopheneyl, triazinyl, benzimidazolyl, phenanthrolinel, and -Si(Q) 31 (Q) 32 (Q) 33 ),
[0177] Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl,
[0178] d2 can be an integer from 0 to 2.
[0179] d3 can be an integer from 0 to 3.
[0180] d4 can be an integer from 0 to 4.
[0181] d5 can be an integer from 0 to 5.
[0182] d6 can be an integer from 0 to 6.
[0183] d8 can be an integer from 0 to 8, and
[0184] Both * and *' represent bonding sites with adjacent atoms.
[0185] In Equation 1, a1 and a2 can both be independent integers from 0 to 5.
[0186] In one embodiment, a1 and a2 can each be independently 0, 1, or 2.
[0187] In one embodiment, a1 and a2 can both be 0 or 1 independently.
[0188] Ar1 and Ar2 in Formula 1 can both be independently selected from 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 C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups.
[0189] In one embodiment, Ar1 and Ar2 can each be independently a group represented by one of formulas 5-1 to 5-26 and 6-1 to 6-55:
[0190]
[0191]
[0192]
[0193]
[0194] Among them, in equations 5-1 to 5-26 and equations 6-1 to 6-55,
[0195] Y 31 and Y 32 Each can be independently represented as O, S, C(Z) 33 (Z) 34 ), N(Z 33 ) or Si(Z 33 (Z) 34 ),
[0196] Z 31 To Z 34 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C2-C 20 alkenyl, C2-C 20 Alkyne group, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, phenanthryl, anthracene, benzo[9,10]phenanthryl, pyridyl, pyrimidinyl, carbazole, dibenzofuranyl, dibenzothiopheneyl, and triazineyl.
[0197] e2 can be 1 or 2.
[0198] e3 is an integer from 1 to 3.
[0199] e4 is an integer from 1 to 4.
[0200] e5 is an integer from 1 to 5.
[0201] e6 can be an integer from 1 to 6.
[0202] e7 can be an integer from 1 to 7.
[0203] e9 can be an integer from 1 to 9, and
[0204] * indicates a bonding site with an adjacent atom.
[0205] In Equation 2, Y1 and Y2 can both be independently selected from single bonds, -O-, -S-, and -C(R). 41 (R) 42 )-、-N(R 41 )-、-Si(R 41 (R) 42 )-, -C(=O)-, -S(=O)2-, -B(R 41 )-、-P(R 42 - and -P(=O)(R 41 )-.
[0206] In one embodiment, Y1 and Y2 can both be independently selected from single bonds, -O-, -S-, and -C(R). 41 (R) 42 )- and -N(R 41 )-.
[0207] In Equation 2, Y3 can be N, B, P, P (=O) or P (=S).
[0208] In Equation 2, CY1 to CY3 can each be independently C5-C. 60 Carbocyclic or C1-C 60 Heterocyclic group.
[0209] In one embodiment, CY1 to CY3 can each be independently selected from:
[0210] Groups represented by formula CY-1, phenyl groups, naphthyl groups, anthracene groups, phenanthrene groups, benzo[9,10]phenanthrene groups, pyrene groups, Groups, cyclopentadienyl group, 1,2,3,4-tetrahydronaphthyl group, furan group, thiophene group, thiophene group, indene group, fluorene group, indole group, carbazole group, benzofuran group, dibenzofuran group, benzothiophene group, dibenzothiophene group, benzothiophene group, dibenzothiophene group, indolepyrimidine group, indolepyrimidine group, benzofuranpyrimidine group, benzothiophenpyrimidine group, benzothiophenpyrimidine group, indolepyrimidine group, benzofuranpyrimidine group, benzothiophenpyrimidine group, dihydropyrimidine group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group Quinazolinyl group, phenanthrene-rhein group, pyrrole group, pyrazole group, imidazole group, 2,3-dihydroimidazolium group, triazole group, 2,3-dihydrotriazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, 2,3-dihydrobenzimidazole group, imidazopyridine group, 2,3-dihydroimidazopyridine group, imidazopyrimidine group, 2,3-dihydroimidazopyrimidine group, imidazopyrazine group, 2,3-dihydroimidazopyrazine group, benzoxazole group, benzothiazole group, benzooxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group and 5,6,7,8-tetrahydroquinoline group:
[0211] Formula CY-1
[0212]
[0213] In equation CY-1,
[0214] Y 11 and Y 12 Each can be independently selected from single bonds, -O-, -S-, -C(R) 51 (R) 52 )-、-N(R 51 )-、-Si(R 51 (R) 52 )-, -C(=O)-, -S(=O)2-, -B(R 51 )-、-P(R 52 - and -P(=O)(R 51 )-,
[0215] Y 13 It can be N, B, P, P (=O) or P (=S),
[0216] CY 11 To CY 13They can all be independently selected from phenyl groups, naphthyl groups, fluorene groups, pyridine groups, pyrimidine groups, triazine groups, benzofuran groups, benzothiophene groups, quinoline groups, isoquinoline groups, quinazoline groups, carbazole groups, dibenzofuran groups, dibenzothiophene groups, and dibenzothiophene groups, and
[0217] R 51 and R 52 They can all independently bind with R 41 and R 42 The descriptions are the same.
[0218] In one embodiment, CY1 to CY3 can all be independently selected from groups represented by formula CY-1, phenyl groups, naphthyl groups, fluorene groups, pyridine groups, pyrimidine groups, triazine groups, benzofuran groups, benzothiophene groups, quinoline groups, isoquinoline groups, quinazoline groups, carbazole groups, dibenzofuran groups, dibenzothiophene groups, and dibenzothiophene groups.
[0219] R1 to R8 and R in Equations 1 and 2 10 R 20 R 30 R 41 and R 42 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, 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 C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60The compounds are heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2).
[0220] In one embodiment, R1 to R8, R 10 R 20 R 30 R 41 and R 42 Each can be independently selected from:
[0221] Hydrogen, deuterium, -F, -Cl, -Br, -I, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, vinyl, propenyl, butenyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, and tert-butoxy; and
[0222] A group represented by one of formulas 5-1 to 5-26 and 6-1 to 6-55.
[0223] In one embodiment, R1 to R8, R 10 R 20 R 30 R 41 and R 42 Each of these can be independently selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl and C1-C 20 Alkoxy;
[0224] All are substituted with at least one of the C1-C groups selected from deuterium, -F, -Cl, -Br, -I, cyano, phenyl, and biphenyl. 20 Alkyl and C1-C 20 Alkoxy;
[0225] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl, dibenzothiophenyl, and dibenzothiophenyl; and
[0226] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, cyano, and C1-C. 20 Alkyl, C1-C 20 The phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophene, and dibenzothiophene are selected from at least one of alkoxy, phenyl, and biphenyl.
[0227] From R in Equation 2 10 R20 R 30 R 41 and R 42 Two or more substituents selected may optionally connect to each other to form substituted or unsubstituted C5-C. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group.
[0228] In Equation 2, b10, b20, and b30 can each be an integer from 1 to 8 independently.
[0229] Replacement C3-C 10 Cycloalkylene, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 aryl, substituted C1-C 60 Hybrid aryl, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heterocyclic group, substituted C5-C 60 Carbocyclic groups, substituted C1-C 60 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 heteroaryl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 At least one substituent among heteroarylsulfo, substituted monovalent nonaromatic condensed polycyclic group, and substituted monovalent nonaromatic condensed heterocyclic group may be selected from:
[0230] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;
[0231] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, and C3-C. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic 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 Choose at least one of the C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;
[0232] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heterocyclic group;
[0233] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic 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 Choose at least one of the C3-C options. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic condensed heterocyclic; and
[0234] -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 ),
[0235] Among them, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, biphenyl and terphenyl.
[0236] According to one embodiment, the host compound may be selected from compounds 1-1 to 1-143:
[0237]
[0238]
[0239]
[0240]
[0241]
[0242]
[0243] According to one embodiment, the dopant compound may be selected from compounds 2-1 to 2-75:
[0244]
[0245]
[0246]
[0247]
[0248]
[0249] In one embodiment, the HOMO level (HOMO) of the host compound in the emitter layer EM1 ) and HOMO levels of dopant compounds (HOMO EM2 This satisfies Formula 2:
[0250] Formula 2
[0251] 0.1eV <||HOMO EM1 |-|HOMO EM2 ||<0.9eV.
[0252] When the host compound and dopant compound in the emitter layer satisfy Equation 2, the hole trapping phenomenon (e.g., hole capture) in the emitter layer can be improved. Therefore, holes can be smoothly injected into the emitter layer, and organic light-emitting devices with high efficiency and long lifetime can be obtained.
[0253] Based on approximately 100 parts by weight of the main body, the amount of dopant in the emitter layer can be from approximately 0.01 parts by weight to approximately 15 parts by weight, but the embodiments of this disclosure are not limited thereto.
[0254] The thickness of the emission layer can be approximately to approximately For example, for about to approximately When the thickness of the emitting layer is within this range, excellent light emission characteristics can be obtained without significantly increasing the driving voltage.
[0255] Because it includes an emitting layer with the above structure, organic light-emitting devices can have high efficiency and long lifespan.
[0256] According to an embodiment, the amount of the host compound in the emitter layer can be greater than the amount of the dopant compound.
[0257] In addition to the host compound and dopant compound that satisfy Formula 1, the emitter layer may also include any other suitable host or dopant.
[0258] In one or more embodiments, the host compound may further include a compound represented by formula 301:
[0259] Formula 301
[0260] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .
[0261] In Equation 301,
[0262] Ar 301 C5-C can be substituted or unsubstituted. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group,
[0263] xb11 can be 1, 2, or 3.
[0264] L 301 It can be selected from substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed heterocyclic groups,
[0265] xb1 can be an integer from 0 to 5.
[0266] R 301 It can be selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, 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 nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, -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
[0267] xb21 can be an integer from 1 to 5.
[0268] Among them, Q 301 To Q 303 Each can be independently selected from C1-C 10 Alkyl, C1-C 10Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, but the embodiments disclosed herein are not limited thereto.
[0269] In one embodiment, Ar in formula 301 301 It can be selected from:
[0270] Naphthalene group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, Groups, tetraphenyl groups, styrene groups, perylene groups, pentylenetetrazol groups, indene-anthracene groups, dibenzofuran groups, and dibenzothiophene groups; and
[0271] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, 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 The following groups are selected from at least one of the following groups: naphthyl group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, Groups, tetraphenyl group, furan group, perylene group, pentylenetetrazol group, indene-anthracene group, dibenzofuran group and dibenzothiophene group,
[0272] Among them, Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, but the embodiments disclosed herein are not limited thereto.
[0273] When xb11 in equation 301 is 2 or greater, two or more Ar 301 It can be connected via a single key.
[0274] In one or more embodiments, the compound represented by formula 301 may be represented by one of formulas 301-1 and 301-2:
[0275] Formula 301-1
[0276]
[0277] Formula 301-2
[0278]
[0279] In Equations 301-1 and 301-2,
[0280] A 301 To A 304 They can all be independently selected from benzene rings, naphthalene rings, phenanthrene rings, fluoranthene rings, benzo[9,10]phenanthrene rings, pyrene rings, Rings, pyridine rings, pyrimidine rings, indene rings, fluorene rings, spirobisfluorene rings, benzo[a]fluorene rings, dibenzo[a]fluorene rings, indole rings, carbazole rings, benzo[a]carbazole rings, dibenzo[a]carbazole rings, furan rings, benzo[a]furan rings, dibenzo[a]furan rings, naphtho[a]furan rings, benzo[a]naphtho[a]furan rings, dinaphtho[a]furan rings, thiophene rings, benzo[a]thiophene rings, dibenzo[a]thiophene rings, naphtho[a]thiophene rings, benzo[a]naphtho[a]thiophene rings, and dinaphtho[a]thiophene rings.
[0281] X 301 It can be O, S or N-[(L 304 ) xb4 -R 304 ],
[0282] R 311 To R 314 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, 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 ),
[0283] xb22 and xb23 can each be independently 0, 1, or 2.
[0284] L 301 xb1, R 301 and Q 31 To Q 33Each can be independently identical to the one described above.
[0285] L 302 To L 304 Each can independently bind with L 301 The descriptions are the same.
[0286] xb2 to xb4 can all be independently identical to those described in conjunction with xb1, and
[0287] R 302 To R 304 They can all independently bind with R 301 The descriptions are the same.
[0288] For example, L in Equations 301, 301-1, and 301-2 301 To L 304 Each can be independently selected from:
[0289] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenylanethyl, benzo[9,10]phenanthrene, pyrene, phenanthrene Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrenediyl, acridineyl, phenanthrene-rheinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl; and
[0290] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazole, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridinyl Azinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, 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 The following are selected from at least one of the following: phenylene, naphthylene, fluorene, spirodifluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenanthrene, anthracene, fluoranthracene, benzo[9,10]phenanthrene, pyrene, etc. Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthreneridinyl, acridineyl, phenanthrene-pyridinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl,
[0291] Among them, Q 31 To Q 33 Each can be independently identical to the one described above.
[0292] In one embodiment, R in Equations 301, 301-1, and 301-2 301 To R 304Each can be independently selected from:
[0293] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0294] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazole, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridinyl Azinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, 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) 32The following are selected from at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthraceneyl, fluoranthraceneyl, benzo[9,10]phenanthryl, pyreneyl, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl.
[0295] Among them, Q 31 To Q 33 Each can be independently identical to the one described above.
[0296] In one or more embodiments, the host may include an alkaline earth metal complex. For example, the host may be selected from Be complexes (e.g., compound H55) and Mg complexes. In some embodiments, the host may be a Zn complex.
[0297] The main body may include at least one selected from 9,10-bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), 9,10-bis(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-bis-9-carbazolylbenzene (mCP), 1,3,5-tris(carbazolyl-9-yl)benzene (TCP) and compounds H1 to H55, but the embodiments of this disclosure are not limited thereto:
[0298]
[0299]
[0300]
[0301] For example, the emitter layer may also include an organometallic complex represented by formula 401:
[0302] Formula 401
[0303] M(L 401 ) xc1 (L 402 ) xc2
[0304] Formula 402
[0305]
[0306] In Equations 401 and 402,
[0307] M can be selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), and thulium (Tm).
[0308] L 401 It can be a ligand represented by Equation 402, and xc1 can be 1, 2, or 3, wherein when xc1 is 2 or greater, two or more L... 401 They can be the same or different from each other.
[0309] L 402 It can be an organic ligand, and xc2 can be an integer from 0 to 4, where when xc2 is 2 or greater, two or more L... 402 They can be the same or different from each other.
[0310] X 401 To X 404 They can each be nitrogen or carbon independently.
[0311] X 401 and X 403 It can be connected via a single or double key, X 402 and X 404 It can be connected via a single key or a double key.
[0312] A 401 and A 402 Each can be independently C5-C 60 Carbocyclic or C1-C 60 Heterocyclic group,
[0313] X 405 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q) 411 )-*'、*-C(Q 411 (Q) 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 ) = *' or * = C = *', where Q 411 and Q 412 It can be hydrogen, deuterium, or C1-C. 20 Alkyl, C1-C 20Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl,
[0314] X 406 It can be a single bond, O, or S.
[0315] R 401 and R 402 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 20 Alkyl, substituted or unsubstituted C1-C 20 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, 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 nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, -Si(Q 401 (Q) 402 (Q) 403 -N(Q) 401 (Q) 402 -B(Q) 401 (Q) 402 -C(=O)(Q) 401 -S(=O)2(Q) 401 ) and -P(=O)(Q 401 (Q) 402 ), and Q 401 To Q 403 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, C6-C 20 Aryl and C1-C 20 Mixed aromatics,
[0316] xc11 and xc12 can both be independent integers from 0 to 10, and
[0317] In Equation 402, * and *' both represent the binding position with M in Equation 401.
[0318] In one embodiment, A in Equation 402 401 and A 402They can all be independently selected from phenyl groups, naphthyl groups, fluorene groups, spirodifluorene groups, indene groups, pyrrole groups, thiophene groups, furan groups, imidazole groups, pyrazole groups, thiazole groups, isothiazole groups, oxazole groups, isoxazole groups, pyridine groups, pyrazine groups, pyrimidine groups, pyridazine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, quinoxaloline groups, quinazoline groups, carbazole groups, benzimidazole groups, benzofuran groups, benzothiophene groups, isobenzothiophene groups, benzooxazole groups, isobenzooxazole groups, triazole groups, tetraazole groups, oxadiazole groups, triazine groups, dibenzofuran groups, and dibenzothiophene groups.
[0319] In one or more embodiments, in formula 402, i)X 401 It can be nitrogen, X 402 It can be carbon, or ii)X 401 and X 402 Both can be nitrogen.
[0320] In one or more embodiments, R in Formula 402 401 and R 402 Each can be independently selected from:
[0321] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl and C1-C 20 Alkoxy;
[0322] All are substituted with at least one of the following C1-C groups selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, phenyl, naphthyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, and norbornyl. 20 Alkyl and C1-C 20 Alkoxy;
[0323] Cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiophenyl;
[0324] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20The cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl groups selected from at least one of the following: cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, and dibenzothiopheneyl groups; and
[0325] -Si(Q 401 (Q) 402 (Q) 403 -N(Q) 401 (Q) 402 -B(Q) 401 (Q) 402 -C(=O)(Q) 401 -S(=O)2(Q) 401 ) and -P(=O)(Q 401 (Q) 402 ),
[0326] Among them, Q 401 To Q 403 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, and naphthyl groups are used, but the embodiments disclosed herein are not limited thereto.
[0327] In one or more embodiments, when xc1 in equation 401 is 2 or greater, two or more L 401 The two A's in 401 Optionally via X 407 (X 407 As connecting bases, two A's are connected to each other. 402 Optionally via X 408 (X 408 (As linking groups) they are connected to each other (see compounds PD1 to PD4 and PD7). X 407 and X 408 They can all be independent single bonds, *-O-*', *-S-*', *-C(=O)-*', *-N(Q) 413 )-*'、*-C(Q 413 (Q) 414 )-*' or *-C(Q 413 )=C(Q 414 )-*'(where Q 413 and Q414 They can all be independently hydrogen, deuterium, or C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl or naphthyl), but the embodiments disclosed herein are not limited thereto.
[0328] L in Equation 401 402 It can be a monovalent, divalent, or trivalent organic ligand. For example, L... 402 The components may be selected from halogens, diketones (e.g., acetylacetone (compound)), carboxylic acids (e.g., pyridinecarboxylic acid (salt)), -C (=O), isonitriles, -CN and phosphorus-containing substances (e.g., phosphine or phosphorous acid (salt)), but the embodiments disclosed herein are not limited thereto.
[0329] In one or more embodiments, the emitter layer may further include one or more organometallic complexes selected from compounds PD1 to PD25:
[0330]
[0331]
[0332] In one or more embodiments, the emission layer may include an arylamine compound or a styreneamine compound.
[0333] In one or more embodiments, the emission layer may include a compound represented by Formula 501:
[0334] Formula 501
[0335]
[0336] In Equation 501,
[0337] Ar 501 C5-C can be substituted or unsubstituted. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group,
[0338] L 501 To L 503 Each can be independently selected from substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60Hybrid aryl, substituted or unsubstituted divalent nonaromatic condensed polycyclic groups and substituted or unsubstituted divalent nonaromatic condensed heterocyclic groups,
[0339] xd1 to xd3 can each be an independent integer from 0 to 3.
[0340] R 501 and R 502 Each can be independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, 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 nonaromatic condensed polycyclic groups, and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, and
[0341] xd4 can be an integer from 1 to 6.
[0342] In one embodiment, Ar in Formula 501 501 It can be selected from:
[0343] Naphthyl group, heptadene group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Groups, tetraphenyl groups, styrene groups, perylene groups, pentylenetetrazol groups, indene-anthracene groups, and indene-phenanthrene groups; and
[0344] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 The naphthyl group selected from at least one of alkoxy, phenyl, biphenyl, terphenyl and naphthyl, heptadene group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Groups, tetraphenyl group, styrene group, perylene group, penfenol group, indene-anthracene group and indene-phenanthrene group.
[0345] In one or more embodiments, L in Formula 501 501 To L 503 Each can be independently selected from:
[0346] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenylanethyl, benzo[9,10]phenanthrene, pyrene, phenanthrene alkyl, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazoyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoyl, dibenzocarbazoyl, dibenzothiopheneyl, and pyridylene; and
[0347] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, The following are selected from at least one of the following groups: phenylene, perylene, pentofenyl, nehexaphenyl, nepentylphenyl, thiophenyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiophenolyl, and pyridyl; phenylene, naphthylene, fluoreneylene, spirodifluoreneyl, benzo[9,10]fluoreneyl, dibenzo[9,10]fluoreneyl, phenanthreneyl, anthraceneylene, fluorenyleneyl, benzo[9,10]phenanthreneyl, pyreneyleneyl, etc. The compounds are: alkyl, perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazoyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoyl, dibenzothiopheneyl, dibenzothiopheneyl, and pyridylene.
[0348] In one or more embodiments, R in Formula 501 501 and R 502 Each can be independently selected from:
[0349] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene alkyl, peryl, pentyranyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, and pyridyl; and
[0350] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, alkyl, peryl, pentyranyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl and -Si(Q) 31 (Q) 32 (Q) 33 The following are selected from at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthraceneyl, fluoranthraceneyl, benzo[9,10]phenanthryl, pyreneyl, The following groups are listed: alkyl, peryl, pentyranyl, benzohexaphenyl, benzopentaphenyl, thienyl, furanyl, carbazoleyl, indoleyl, isoindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazoleyl, dibenzocarbazoleyl, dibenzothiopheneyl, and pyridyl.
[0351] Among them, Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0352] In one or more embodiments, xd4 in Formula 501 can be 2, but the embodiments of this disclosure are not limited thereto.
[0353] In one or more embodiments, the emitter layer may further include one or more compounds selected from compounds FD1 to FD22:
[0354]
[0355]
[0356]
[0357] In one or more embodiments, the emitter layer may further include compounds selected from the following compounds, but the embodiments are not limited thereto:
[0358]
[0359] According to one embodiment, the emitting layer can emit blue light with a maximum emission wavelength of about 410 nm to about 490 nm.
[0360] According to one embodiment, the emitter layer may include doped and undoped regions. The doped regions may include a host compound and a dopant compound, while the undoped regions may include the host compound.
[0361] When the emitter layer includes doped and undoped regions as described above, exciton leakage from the emitter layer can be prevented or reduced.
[0362] In one or more embodiments, when the emitter layer includes doped and undoped regions, the undoped regions may be composed of a host compound. In one or more embodiments, the undoped regions may not include a dopant compound.
[0363] In one embodiment, when the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer can be patterned as a red emission layer, a green emission layer, or a blue emission layer, depending on the sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from red, green, and blue emission layers, wherein the two or more layers may be in contact with each other or may be separated from each other. In one or more embodiments, the emission layer may include two or more materials selected from red, green, and blue luminescent materials, wherein the two or more materials may be mixed with each other in a single layer to emit white light.
[0364] In one embodiment, in an organic light-emitting device...
[0365] The emission layer is the first color light emission layer.
[0366] The organic light-emitting device may further include, between the first electrode and the second electrode: i) at least one second-color light-emitting layer, or ii) at least one second-color light-emitting layer and at least one third-color light-emitting layer.
[0367] The maximum emission wavelengths of the first color light, the second color light, and the third color light may be the same as or different from each other, and
[0368] The first color light and the second color light can be emitted in the form of a mixed light, or the first color light, the second color light and the third color light can be emitted in the form of a mixed light.
[0369] Electron transport region in organic layer 150
[0370] According to one embodiment, the organic layer 150 may further include an electron transport region disposed between the emitter layer and the second electrode.
[0371] The electron transport region can have: i) a single-layer structure comprising a single material; ii) a single-layer structure comprising multiple different materials; or iii) a multi-layer structure comprising multiple layers comprising multiple different materials.
[0372] 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 embodiments of this disclosure are not limited thereto.
[0373] 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 the constituent layers of each structure are stacked sequentially from the emitter layer in the order stated herein. However, embodiments of the electron transport region structure are not limited to these.
[0374] The electron transport region (including, for example, a buffer layer, a hole blocking layer, an electron control layer, and / or an electron transport layer) may comprise a metal-free compound containing at least one π-electron-depleted nitrogen-containing ring.
[0375] The term "π-electron-poor nitrogen-containing ring" refers to a C1-C ring having at least one *-N=*' moiety as the cyclic part. 60 Heterocyclic group.
[0376] For example, the term "π-electron-poor nitrogen-containing ring" can refer to: i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' moiety; ii) a heteropolycyclic group in which two or more 5- to 7-membered heteromonocyclic groups, each having at least one *-N=*' moiety, are condensed together; or iii) at least one of the 5- to 7-membered heteromonocyclic groups, each having at least one *-N=*' moiety, is combined with at least one C5-C 60 Heterocyclic groups formed by the condensation of carbocyclic groups.
[0377] Non-limiting examples of π-electron-depleted nitrogen-containing rings include imidazole rings, pyrazole rings, thiazole rings, isothiazole rings, oxazole rings, isoxazole rings, pyridine rings, pyrazine rings, pyrimidine rings, pyridazine rings, indazole rings, purine rings, quinoline rings, isoquinoline rings, benzo[a]quinoline rings, phthalazine rings, naphthidine rings, quinoxaline rings, quinazoline rings, cyclophosphine rings, phenanthridine rings, acridine rings, phenanthrene-rhein rings, phenazine rings, benzimidazole rings, isobenzo[a]thiazole rings, benzo[a]oxazole rings, isobenzo[a]oxazole rings, triazole rings, tetraazole rings, oxadiazole rings, triazine rings, thiadiazole rings, imidazo[a]pyridine rings, imidazo[a]pyrimidine rings, and azacarbazole rings.
[0378] For example, the electron transport region may include a compound represented by Formula 601:
[0379] Formula 601
[0380] [Ar601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0381] In Equation 601,
[0382] Ar 601 C5-C can be substituted or unsubstituted. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group,
[0383] xe11 can be 1, 2, or 3.
[0384] L 601 It can be selected from substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent nonaromatic condensed polycyclic groups and substituted or unsubstituted divalent nonaromatic condensed heterocyclic groups,
[0385] xe1 can be an integer from 0 to 5.
[0386] R 601 It can be selected from substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, 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 nonaromatic condensed polycyclic groups, substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups, -Si(Q 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) and -P(=O)(Q 601 (Q) 602 ),
[0387] Q 601 To Q 603 Each can be independently C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and
[0388] xe21 can be an integer from 1 to 5.
[0389] In one embodiment, xe11 Ar 601 and xe21 R 601 At least one of them may include a nitrogen-containing ring that is π-electron depleted.
[0390] In one embodiment, Ar in Formula 601 601 It can be selected from:
[0391] Phenyl group, naphthyl group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, Groups, tetraphenyl groups, styrene groups, perylene groups, pentylenetetrazol groups, indoxanthracene groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, imidazole groups, pyrazole groups, thiazole groups, isothiazole groups, oxazole groups, isoxazole groups, pyridine groups, pyrazine groups, pyrimidine groups, pyridazine groups, indazole groups, purine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, phthalazine groups, naphthidine groups, quinoxaloline groups, quinazolinoline groups, cyclophosphine groups, phenanthridine groups, acridine groups, phenanthrene-rhein groups, phenazine groups, benzimidazole groups, isobenzothiazole groups, benzoxazole groups, isobenzoxazole groups, triazole groups, tetraazole groups, oxadiazole groups, triazine groups, thiadiazole groups, imidazopyridine groups, imidazopyrimidine groups, and azacarbazole groups; and
[0392] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-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 The phenyl group, naphthyl group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, selected from at least one of the following: Groups, tetraphenyl group, styrene group, perylene group, pentylenetetrazol group, indoxanthracene group, dibenzofuran group, dibenzothiophene group, carbazole group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthidine group, quinoxaline group, quinazolinoline group, cyclophosphine group, phenanthridine group, acridine group, phenanthrene-rhein group, phenazine group, benzimidazole group, isobenzothiazole group, benzooxazole group, isobenzooxazole group, triazole group, tetraazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, and azacarbazole group,
[0393] Among them, Q 31 To Q 33 Each can be independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0394] When xe11 in equation 601 is 2 or greater, two or more Ar 601 They can be connected to each other via a single key.
[0395] In one or more embodiments, Ar in Formula 601 601 It can be an anthracene group.
[0396] In one or more embodiments, the compound represented by formula 601 can be represented by formula 601-1:
[0397] Formula 601-1
[0398]
[0399] In Equation 601-1,
[0400] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), and X 614 To X 616 At least one of them can be N,
[0401] L 611 To L 613 Each can independently bind with L 601 The descriptions are the same.
[0402] xe611 to xe613 can all be independently identical to those described in conjunction with xe1.
[0403] R 611 To R 613 They can all independently bind with R 601 The descriptions are the same, and
[0404] R 614 To R 616 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0405] In one embodiment, L in Equation 601 601 L in Equation 601-1 611 To L 613 Each can be independently selected from:
[0406] Phenylidene, naphthylene, fluorene, spirodifluorene, benzo[a]fluorene, dibenzo[a]fluorene, phenanthrene, anthracene, fluorenylanethyl, benzo[9,10]phenanthrene, pyrene, phenanthrene Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthrenediyl, acridineyl, phenanthrene-rheinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl; and
[0407] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazine The following are at least one of the following groups selected from: phenylene, naphthidyl, quinoxolinyl, quinazolinyl, phenanthrynyl, phenanthrinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl; phenylene, naphthylene, fluorene, spirodifluorene, benzo[9,10]fluorene, dibenzo[9,10]fluorene, phenanthrynyl, anthraceneyl, fluoranthraceneyl, benzo[9,10]phenanthrynyl, pyreneylyl, etc. Perylene, pentafenyl, hexaphenylene, pentaphenylene, thiopheneyl, furanyl, carbazolyl, indoleyl, isoyindoleyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiopheneyl, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, quinoxalinyl, phenanthreneridinyl, acridineyl, phenanthrene-pyridinyl, benzimidazolyl, isobenzothiazolyl, benzimidazolyl, isobenzoxazolyl, isobenzoxazolyl, triazoleyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and zazacarbazolyl,
[0408] However, the embodiments disclosed herein are not limited thereto.
[0409] In one or more embodiments, xe1 in Formula 601 and xe611 to xe613 in Formula 601-1 can each be independently 0, 1 or 2.
[0410] In one or more embodiments, R in Formula 601 601 R in equation 601-1 611 To R 613 Each can be independently selected from:
[0411] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cinolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl;
[0412] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thiophene, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalyl The phenyl, biphenyl, terphenyl, naphthinyl, quinoxalinyl, quinazolinyl, terazolinyl, phenanthrynyl, acridineyl, phenanthrynyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidinyl, and azacarbazolyl are selected from at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]fluorenyl, dibenzo[9,10]fluorenyl, pyrene, Peryl, pentylenyl, hexaphenyl, pentaphenyl, thienyl, furanyl, carbazole, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl Pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cenolinyl, phenanthridineyl, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0413] -S(=O)2(Q 601 ) and -P(=O)(Q 601 (Q) 602 ),
[0414] Among them, Q 601 and Q 602 Each can be independently identical to the one described above.
[0415] The electron transport region may include at least one compound selected from compounds ET1 to ET36, but embodiments of this disclosure are not limited thereto:
[0416]
[0417]
[0418]
[0419]
[0420] In one or more embodiments, the electron transport region may include at least one compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ.
[0421]
[0422] The thicknesses of the buffer layer, hole blocking layer, and electronic control layer can all be independently set to approximately [value missing]. to approximately For example, for about to approximately When the thicknesses of the buffer layer, hole blocking layer, and electronic control layer are within these ranges, excellent hole blocking characteristics and / or excellent electronic control characteristics can be obtained without significantly increasing the driving voltage.
[0423] The thickness of the electron transport layer can be approximately to approximately For example, for about to approximately When the thickness of the electron transport layer is within the above range, the electron transport layer can have satisfactory electron transport characteristics without significantly increasing the driving voltage.
[0424] In addition to the materials mentioned above, the electron transport region (e.g., the electron transport layer in the electron transport region) may also include metallic materials.
[0425] According to one embodiment, the electron transport region may include a metallic material.
[0426] The metal-containing material may include at least one selected from alkali metal complexes and alkaline earth metal complexes. Alkali metal complexes may include metal ions selected from lithium (Li) ions, sodium (Na) ions, potassium (K) ions, rubidium (Rb) ions, and cesium (Cs) ions, while alkaline earth metal complexes may include metal ions selected from beryllium (Be) ions, magnesium (Mg) ions, calcium (Ca) ions, strontium (Sr) ions, and barium (Ba) ions. The ligand coordinated to the metal ion of the alkali metal complex or alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, and cyclopentadiene, but the embodiments of this disclosure are not limited thereto.
[0427] In some embodiments, for example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium hydroxyquinoline, LiQ) or compound ET-D2:
[0428]
[0429] The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.
[0430] The electron injection layer can have: i) a single-layer structure comprising a single material; ii) a single-layer structure comprising multiple different materials; or iii) a multi-layer structure comprising multiple layers comprising multiple different materials.
[0431] 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.
[0432] 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.
[0433] The alkaline earth metal may be selected from magnesium (Mg), calcium (Ca), strontium (Sr), and barium (Ba).
[0434] The rare earth metal may be selected from scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb), and gadolinium (Gd).
[0435] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may each independently be selected from oxides and halides (e.g., fluorides, chlorides, bromides, and / or iodides) of the alkali metal, the alkaline earth metal, and the rare earth metal.
[0436] The alkali metal compound may be selected from alkali metal oxides (such as Li2O, Cs2O, or K2O) 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, Li2O, NaF, LiI, NaI, CsI, and KI, but the embodiments of the present disclosure are not limited thereto.
[0437] 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.
[0438] The rare earth metal compound may be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, and TbF3. In one embodiment, the rare earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but the embodiments of the present disclosure are not limited thereto.
[0439] Alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may respectively include alkali metal ions, alkaline earth metal ions, and rare earth metal ions as described above, and the ligands coordinated with the metal ions of alkali metal complexes, alkaline earth metal complexes, or rare earth metal complexes may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, and cyclopentadiene, but the embodiments of this disclosure are not limited thereto.
[0440] 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 as described above (e.g., it may consist of 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 as described above). In one or more embodiments, the electron injection layer may also include organic materials. When the electron injection layer further includes organic materials, the 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 combinations thereof may be uniformly or non-uniformly dispersed in a matrix comprising organic materials.
[0441] The thickness of the electron injection layer can be approximately to approximately For example, for about to approximately When the thickness of the electron injection layer is within the above range, the electron injection layer can have satisfactory electron injection characteristics without significantly increasing the driving voltage.
[0442] Second electrode 190
[0443] The second electrode 190 is disposed on the organic layer 150 having such a structure. The second electrode 190 can be a cathode serving as an electron injection electrode. In this respect, the material used to form the second electrode 190 can be selected from metals, alloys, conductive compounds, and combinations thereof, all of which have relatively low work functions.
[0444] 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 embodiments of this disclosure are not limited thereto. The second electrode 190 may be a transmission electrode, a semi-transmission electrode, or a reflection electrode.
[0445] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.
[0446] Figures 2 to 4 Description
[0447] In one embodiment, the organic light-emitting device may further include a capping layer disposed on the first electrode and / or the second electrode.
[0448] according to Figure 2 An example organic light-emitting device 20 has a structure in which a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190 are stacked sequentially in the order stated herein. Figure 3 An example organic light-emitting device 30 has a structure in which a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 are stacked sequentially in the order stated herein. Figure 4 An example organic light-emitting device 40 has a structure in which a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 are stacked sequentially in the order stated above.
[0449] about Figures 2 to 4 The first electrode 110, the organic layer 150, and the second electrode 190 can all be bonded by reference. Figure 1 Use the given description to understand.
[0450] In each of the organic layers 150 of organic light-emitting devices 20 and 40, light generated in the emitting layer can pass outward through the first electrode 110 (which is a semi-transparent electrode or a transmissive electrode) and the first capping layer 210. In each of the organic layers 150 of organic light-emitting devices 30 and 40, light generated in the emitting layer can pass outward through the second electrode 190 (which is a semi-transparent electrode or a transmissive electrode) and the second capping layer 220.
[0451] The first capping layer 210 and the second capping layer 220 can improve the external light emission efficiency of the device based on the principle of constructive interference.
[0452] The first capping layer 210 and the second capping layer 220 can each be independently an organic capping layer including organic materials, an inorganic capping layer including inorganic materials, or a composite capping layer including both organic and inorganic materials.
[0453] The first capping layer 210 and the second capping layer 220 can each independently have a refractive index of 1.6 or higher relative to a wavelength of 589 nm.
[0454] At least one of the first capping layer 210 and the second capping layer 220 may each independently comprise at least one material selected from carbocyclic compounds, heterocyclic compounds, amine compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalenephthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compound, heterocyclic compound, and amine compound may each optionally be substituted with substituents comprising at least one element selected from oxygen (O), nitrogen (N), sulfur (S), selenium (Se), silicon (Si), fluorine (F), chlorine (Cl), bromine (Br), and iodine (I). In one embodiment, at least one of the first capping layer 210 and the second capping layer 220 may each independently comprise an amine compound.
[0455] In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include a compound represented by formula 201 or a compound represented by formula 202.
[0456] In one or more embodiments, at least one of the first capping layer 210 and the second capping layer 220 may each independently comprise a compound selected from compounds HT28 to HT33 and compounds CP1 to CP5, but the embodiments of this disclosure are not limited thereto:
[0457]
[0458] In the above text, it has already been combined Figures 1 to 4 An organic light-emitting device according to an embodiment has been described. However, the embodiments disclosed herein are not limited thereto.
[0459] Layers constituting hole transport regions, emission regions, and electron transport regions can be formed in a set or predetermined area 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.
[0460] When forming layers constituting hole transport regions, emitter layers, and electron transport regions by vacuum deposition, depending on the materials to be included and the structure of the layers to be formed, deposition temperatures of approximately 100°C to approximately 500°C and a deposition temperature of approximately 10°C can be used. -8 To about 10 -3 The vacuum degree and about to approximately Vacuum deposition was performed at a deposition rate of [value missing].
[0461] When spin coating is used to form layers constituting hole transport regions, emitter layers, and electron transport regions, spin coating can be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80°C to about 200°C, depending on the material to be included and the structure of the layers to be formed.
[0462] equipment
[0463] Organic light-emitting devices can be included in any suitable device.
[0464] Another aspect of this disclosure provides an apparatus including an organic light-emitting device.
[0465] For example, the device may be a light-emitting device, an authentication device, or an electronic device, but the embodiments disclosed herein are not limited thereto.
[0466] Light-emitting devices can be used as any suitable display, light source, etc.
[0467] Authentication devices can be, for example, biometric authentication devices used to authenticate individuals using biometric information from a biometric body (e.g., fingertip, pupil, etc.).
[0468] In addition to organic light-emitting devices, authentication equipment can also include biometric information collectors.
[0469] Electronic devices can be applied to personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, video game consoles, medical instruments (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram (ECG) displays, ultrasound diagnostic devices, or endoscopic displays), fish detectors, various measuring instruments, meters (e.g., instruments for vehicles, aircraft, and ships), projectors, etc., but the embodiments of this disclosure are not limited thereto.
[0470] In one embodiment, in addition to the organic light-emitting device, the device may also include a thin-film transistor. Here, the thin-film transistor may include a source electrode, an active layer, and a drain electrode, wherein a first electrode of the organic light-emitting device may be in electrical contact with one of the source electrode and the drain electrode of the thin-film transistor.
[0471] General definition of substituents
[0472] As used herein, the term "C1-C" 60 "alkyl" refers to a straight-chain or branched monovalent group of an aliphatic saturated hydrocarbon having 1 to 60 carbon atoms, and non-limiting examples include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. As used herein, the term "C1-C" is used in conjunction with the alkyl group. 60 "alkylene" refers to a compound with C1-C2 atoms. 60Alkyl groups are divalent groups with essentially the same structure.
[0473] As used herein, the term "C2-C" 60 "Alkenyl" refers to the group formed at C2-C. 60 A hydrocarbon group having at least one carbon-carbon double bond at the middle or end of an alkyl group, non-limiting examples of which include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" is used... 60 "Alkenyl" refers to a group that has a C2-C bond structure. 60 Alkenes are divalent groups with essentially the same structure.
[0474] As used herein, the term "C2-C" 60 "Alkyne group" refers to the group at C2-C 60 A hydrocarbon group having at least one carbon-carbon triple bond at the middle or end of an alkyl group, non-limiting examples of which include ethynyl and propynyl groups. As used herein, the term "C2-C" is used in conjunction with this. 60 "Immyneyl" refers to a group with a C2-C group. 60 The alkynyl group is a divalent group with a basically the same structure.
[0475] As used herein, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups, and non-limiting examples include methoxy, ethoxy, and isopropoxy.
[0476] As used herein, the term "C3-C" 10 "Cycloalkyl" refers to a monocyclic saturated hydrocarbon group having 3 to 10 carbon atoms, and non-limiting examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "C3-C" is also used. 10 "Cycloalkylene" refers to a compound with C3-C66 atoms. 10 Divalent groups with essentially the same structure as cycloalkyl groups.
[0477] As used herein, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as the cyclic atom and 1 to 10 carbon atoms, with non-limiting examples including 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and tetrahydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkyl" refers to a compound with C1-C2 atoms. 10 Divalent groups with essentially the same structure as heterocyclic alkyl groups.
[0478] As used herein, the term "C3-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 being aromatic; non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C" is also used. 10 "Biopylidene alkenyl" refers to a group that has a similar structure to C3-C4. 10 A divalent group with a structure that is essentially the same as a cycloalkenyl group.
[0479] As used herein, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a cyclizing atom, one to ten carbon atoms, and at least one double bond in its ring. C1-C 10 Non-limiting examples of heterocyclic alkenyl groups include 4,5-dihydro-1,2,3,4-oxarizolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl" refers to a group that has a similar structure to C1-C1. 10 Divalent groups with essentially the same structure as heterocyclic alkenyl groups.
[0480] As used here, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system comprising 6 to 60 carbon atoms, and as used herein, "C6-C" 60 "Aryl" refers to a divalent group in a carbocyclic aromatic system having 6 to 60 carbon atoms. (C6-C) 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, and Base. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the two or more rings may be fused together.
[0481] As used herein, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, Si, P, and S as a cyclizing atom in addition to 1 to 60 carbon atoms. As used herein, the term "C1-C" is also relevant. 60 "Hypo-aryl" refers to a divalent group having a heterocyclic aromatic system, wherein the heterocyclic aromatic system has at least one heteroatom selected from N, O, Si, P, and S as a cyclizing atom in addition to 1 to 60 carbon atoms. C1-C 60 Non-limiting examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C1-C 60 heteroaryl and C1-C 60When each heteroaryl group comprises two or more rings, the two or more rings may condense together.
[0482] As used here, the term "C6-C" 60 "Aryloxy group" refers to -OA 102 (where A) 102 For C6-C 60 Aryl), as used herein in the term "C6-C 60 "Arylthio" refers to -SA 103 (where A) 103 For C6-C 60 Aryl).
[0483] As used herein, the term "monovalent nonaromatic condensation polycyclic group" refers to a monovalent group having two or more rings condensed together, with only carbon atoms as cyclic atoms (e.g., 8 to 60 carbon atoms) and lacking aromaticity throughout its molecular structure. Non-limiting examples of monovalent nonaromatic condensation polycyclic groups include fluorenyl and adamantyl. As used herein, the term "divalent nonaromatic condensation polycyclic group" refers to a divalent group having substantially the same structure as a monovalent nonaromatic condensation polycyclic group.
[0484] As used herein, the term "monovalent non-aromatic condensed heterocyclic group" refers to a monovalent group having two or more rings condensed together, at least one heteroatom selected from N, O, Si, P, and S as cyclic atoms in addition to carbon atoms (e.g., 1 to 60 carbon atoms), and lacking aromaticity throughout its molecular structure. Non-limiting examples of monovalent non-aromatic condensed heterocyclic groups include carbazolyl and azadamaneyl. As used herein, the term "divalent non-aromatic condensed heterocyclic group" refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed heterocyclic group.
[0485] As used herein, the term "C5-C" 60 A "carbocyclic group" refers to a monocyclic or polycyclic group consisting of 5 to 60 carbon atoms, with carbon as the only cyclic atom. (C5-C) 60 The carbocyclic group can be an aromatic carbocyclic group or a non-aromatic carbocyclic group. (C5-C) 60 The 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, depending on the connection to C5-C... 60 The number of substituents in the carbocyclic group, C5-C 60 The carbon cyclic group can be a trivalent group or a tetravalent group.
[0486] As used herein, the term "C1-C" 60"Heterocyclic group" refers to a group that, in addition to using at least one heteroatom selected from N, O, Si, P, and S (excluding carbon, which can be 1 to 60 carbon atoms) as a cyclic atom, has a cyclic structure similar to C5-C6. 60 Groups with essentially the same structure as carbon cyclic groups.
[0487] In this specification, C5-C is replaced. 60 Carbocyclic groups, substituted C1-C 60 Heterocyclic groups, substituted C1-C 20 Alkylene, substituted C2-C 20 alkenyl, substituted C3-C 10 Cycloalkylene, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 aryl, substituted C1-C 60 Hybrid aryl, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heterocyclic group, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 heteroaryl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 At least one substituent among heteroarylsulfo, substituted monovalent nonaromatic condensed polycyclic group, and substituted monovalent nonaromatic condensed heterocyclic group may be selected from:
[0488] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;
[0489] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, and C3-C.10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic 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 Choose at least one of the C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl and C1-C 60 Alkoxy;
[0490] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heterocyclic group;
[0491] All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic 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 Choose at least one of the C3-C options. 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic condensed heterocyclic; and
[0492] -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 ),
[0493] Among them, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each group can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic, monovalent non-aromatic condensed heterocyclic, biphenyl and terphenyl.
[0494] As used herein, the term "Ph" refers to phenyl, as used herein, the term "Me" refers to methyl, as used herein, the term "Et" refers to ethyl, and as used herein, the terms "tert-Bu" or "Bu" refer to... t "Refers to tert-butyl, as the term "OMe" used herein refers to methyl methacrylate (MMA).
[0495] As used herein, the term "biphenyl" refers to a phenyl group that has a substituted phenyl group. In other words, "biphenyl" is a phenyl group with a C6-C bond. 60 Aryl groups are examples of substituted phenyl groups.
[0496] As used herein, the term "terphenyl" refers to a phenyl group substituted with biphenyl groups. In other words, "terphenyl" is a phenyl group having C6-C substitutions. 60 C6-C of aryl 60 Aryl groups are examples of substituted phenyl groups.
[0497] Unless otherwise defined, * and *' as used herein refer to the binding site with the adjacent atom in the corresponding expression.
[0498] In the following, the compounds and organic light-emitting devices according to the embodiments will be described in more detail with reference to examples.
[0499] Example
[0500] Example 1
[0501] As the substrate and anode, 15Ω / cm from Corning Incorporated 2 The (120nm) ITO glass substrate was cut into 50mm×50mm×0.5mm pieces, sonicated for 5 minutes each with acetone, isopropanol, and ultrapure water, and then cleaned by exposure to ultraviolet light and ozone for 10 minutes. The ITO glass substrate was then fed into a vacuum deposition apparatus.
[0502] m-MTDATA and F4-TCNQ (3wt%) were vacuum deposited on an ITO anode to form a first hole transport layer with a thickness of 110 nm, and 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 10 nm.
[0503] Then, compounds 1-2 (body) and 2-1 (doper) (3 wt%) are simultaneously (e.g., together) vacuum deposited on the second hole transport layer to form an emitter layer with a thickness of 30 nm. Next, BAlq is deposited on the emitter layer to form a hole blocking layer with a thickness of 10 nm. Alq3 is deposited on the hole blocking layer to form an electron transport layer with a thickness of 30 nm, LiF is deposited on the electron transport layer to form an electron injection layer with a thickness of 1 nm, and Ag is vacuum deposited on the electron injection layer to form a cathode with a thickness of 200 nm, thereby completing the fabrication of the organic light-emitting device.
[0504]
[0505] Examples 2 through 8 and Comparative Examples 1 through 5
[0506] In addition to using the compounds shown in Table 1 as host and dopant compounds, other organic light-emitting devices are fabricated in substantially the same manner as in Example 1.
[0507]
[0508] Comparison Example 6
[0509] The other organic light-emitting devices are fabricated in essentially the same manner as in Example 1, except that the first hole transport layer does not include p-type dopant.
[0510] Evaluation Example 1
[0511] Hole mobility, driving voltage, and efficiency of organic light-emitting devices fabricated according to Examples 1 to 8 and Comparative Examples 1 to 6 were evaluated using an M7000 (manufactured by McScience Inc.), a Keithley SMU 236, and a PR650 Spectroscan Source Measurement Unit (manufactured by PhotoResearch).
[0512] Furthermore, based on the Mott-Gurney equation, the hole mobility of each device is calculated using a "hole-only device" with a structure having a first electrode / first hole transport layer / second hole transport layer / emitter layer / second electrode.
[0513] The results are shown in Table 1:
[0514] [Table 1]
[0515]
[0516] Table 1 confirms that the organic light-emitting devices of Examples 1 to 8 possess excellent hole mobility, low driving voltage, and high efficiency. Furthermore, it is confirmed that the organic light-emitting devices of Examples 1 to 8 have higher hole mobility and efficiency than the organic light-emitting devices of Comparative Examples 1 to 6.
[0517] Organic light-emitting devices can have excellent hole mobility as well as improved efficiency and lifetime.
[0518] As used herein, the terms “basically,” “about,” and similar terms are used as approximate terms rather than as terms of degree, and are intended to explain the inherent biases in measurements or calculations that will be recognized by one of ordinary skill in the art.
[0519] Any numerical range stated herein is intended to include all subranges with the same numerical precision contained within the stated range. For example, the range “1.0 to 10.0” is intended to include all subranges between the stated minimum value 1.0 and the stated maximum value 10.0 (inclusive), that is, 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 limit stated herein is intended to include all lower numerical limits contained therein, and any minimum numerical limit stated in this specification is intended to include all higher numerical limits contained therein. Therefore, the applicant reserves the right to amend this specification (including the claims) to expressly state any subranges contained within the range expressly stated herein.
[0520] It should be understood that the embodiments described herein are to be considered in a descriptive sense only and not for limiting purposes. The description of features or aspects in each embodiment should generally be considered applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the spirit and scope defined by the claims and their equivalents.
Claims
1. An organic light-emitting device, the organic light-emitting device comprising: First electrode; The second electrode faces the first electrode; as well as An organic layer is located between the first electrode and the second electrode. The organic layer includes an emitter layer and a hole transport region located between the first electrode and the emitter layer. The hole transport region includes a first hole transport layer and a second hole transport layer. The first hole transport layer includes a first hole transport compound and a p-type dopant. The second hole transport layer includes a second hole transport compound, and The emitter layer comprises a host compound represented by Formula 1 and a dopant compound represented by Formula 2: Formula 1 Formula 2 , Among them, in Equations 1 and 2, L1 and L2 are both independently single bonds or groups represented by one of formulas 3-1 to 3-36: , Among them, in equations 3-1 to 3-36, Y 11 for -O- '、 -S- 'or -N(Z5)- ', Z1 to Z5 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, dibenzofuranyl, dibenzothiopheneyl, triazinyl, benzimidazolyl, phenanthrolinyl, and -Si(Q) 31 (Q) 32 (Q) 33 ), Q 31 To Q 33 All were independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, d2 is an integer from 0 to 2. d3 is an integer from 0 to 3. d4 is an integer from 0 to 4. d5 is an integer from 0 to 5. d6 is an integer from 0 to 6. d8 is an integer from 0 to 8, and and 'These all represent bonding sites with adjacent atoms,' a1 and a2 are both independently 0, 1, or 2. Ar1 and Ar2 are each independently a group represented by one of formulas 5-1 to 5-26: , In Equations 5-1 to 5-26, Y 31 and Y 32 Each is independently O, S, C(Z) 33 (Z) 34 ), N(Z 33 ) or Si(Z 33 (Z) 34 ), Z 31 To Z 34 Each group is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl group, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, phenanthryl, anthracene, benzo[9,10]phenanthryl, pyridyl, pyrimidinyl, carbazole, dibenzofuranyl, dibenzothiopheneyl, and triazineyl. e2 is 1 or 2. e3 is an integer from 1 to 3. e4 is an integer from 1 to 4. e5 is an integer from 1 to 5. e6 is an integer from 1 to 6. e7 is an integer from 1 to 7. e9 is an integer from 1 to 9, and Indicates the bonding site with adjacent atoms. Y1 and Y2 are both independently selected from single bonds, -O-, -S-, and -C(R). 41 (R) 42 )-、-N(R 41 )-、-Si(R 41 (R) 42 )-, -C(=O)-, -S(=O)2-, -B(R 41 )-、-P(R 42 )- and -P(=O)(R 41 )-, and Y1 and Y2 are not simultaneously -N(R 41 )-, Y3 is N, B, P, P (=O) or P (=S). CY1 to CY3 are each independently selected from: Groups represented by formula CY-1, including phenyl groups, naphthyl groups, fluorene groups, pyridine groups, pyrimidine groups, triazine groups, benzofuran groups, benzothiophene groups, quinoline groups, isoquinoline groups, quinazoline groups, carbazole groups, dibenzofuran groups, dibenzothiophene groups, and dibenzothiophene groups: Formula CY-1 , In equation CY-1, Y 11 and Y 12 Each is independently selected from single bonds, -O-, -S-, and -C(R). 51 (R) 52 )-、-N(R 51 )-、-Si(R 51 (R) 52 )-, -C(=O)-, -S(=O)2-, -B(R 51 )-、-P(R 52 )- and -P(=O)(R 51 )-, Y 13 For N, B, P, P (=O) or P (=S), CY 11 To CY 13 All are independently selected from phenyl groups, naphthyl groups, fluorene groups, pyridine groups, pyrimidine groups, triazine groups, benzofuran groups, benzothiophene groups, quinoline groups, isoquinoline groups, quinazoline groups, carbazole groups, dibenzofuran groups, dibenzothiophene groups, and dibenzothiophene groups, and R 51 and R 52 Each group is independently selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl and C1-C 20 Alkyl groups; all substituted with at least one of the following C1-C groups selected from deuterium, -F, -Cl, -Br, -I, cyano, phenyl, and biphenyl. 20 Alkyl and C1-C 20 Alkoxy; phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl, dibenzothiopheneyl, and dibenzothiopheneyl; and all substituted with deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C1-C 20 The phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl, dibenzothiophenyl, and dibenzothiophenyl group selected from at least one of alkoxy, phenyl, and biphenyl groups. R1 to R8, R 10 R 20 R 30 R 41 and R 42 All were independently selected from: Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl and C1-C 20 Alkoxy; All are substituted with at least one of the C1-C groups selected from deuterium, -F, -Cl, -Br, -I, cyano, phenyl, and biphenyl. 20 Alkyl and C1-C 20 Alkoxy; Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl, dibenzothiophenyl, and dibenzothiophenyl; and All are substituted with groups ranging from deuterium, -F, -Cl, -Br, -I, cyano, and C1-C. 20 Alkyl, C1-C 20 The phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, carbazole, dibenzofuranyl, dibenzothiophenyl, and dibenzothiophenyl group selected from at least one of alkoxy, phenyl, and biphenyl groups. From R 10 R 20 R 30 R 41 and R 42 Two or more substituents selected may optionally connect to each other to form substituted or unsubstituted C5-C. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group, b10, b20, and b30 are each an independent integer from 1 to 8.
2. The organic light-emitting device according to claim 1, wherein, The highest occupied molecular orbital energy level (HOMO) of the first electrode EL1 The highest occupied molecular orbital energy level (HOMO) of the first hole transport layer HT1 And the highest occupied molecular orbital energy level (HOMO) of the second hole transport layer HT2 Satisfying Formula 1: Formula 1 |HOMO EL1 | < |HOMO HT1 | < |HOMO HT2 |。 3. The organic light-emitting device according to claim 1, wherein, Both the first hole transport compound and the second hole transport compound are independently selected from compounds represented by formula 201A and compounds represented by formula 202A: Formula 201A Formula 202A , In Equations 201A and 202A, L 201 To L 203 All were independently selected from substituted or unsubstituted C3-C. 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C1-C 60 Hybrid aryl, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed heterocyclic groups, xa1 to xa3 are all independent integers from 0 to 3. xa5 is an integer from 1 to 10. R 202 To R 204 R 211 and R 212 All were independently selected from substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, 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 nonaromatic condensed polycyclic groups, and substituted or unsubstituted monovalent nonaromatic condensed heterocyclic groups. R 213 To R 216 Each group is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C1-C 10 Alkyl phenyl, substituted -F phenyl, cyclopentadienyl, indene, naphthyl, chamomilecycloyl, heptalenyl, indane, acenaphthyl, fluorenyl, spirodifluorenyl, benzo[9,10]phenanthrene, pyrene, thionyl, tetraphenyl, styrene, peryl, pentofenyl, hexaphenyl, pentaphenyl, rubidyl, benzoyl, ovylphenyl, thiophene, furanyl, carbazolyl, indole, isoindole, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, and pyridyl.
4. The organic light-emitting device according to claim 1, wherein, The p-type dopant has a lowest unoccupied molecular orbital energy level of -3.5 eV or less.
5. The organic light-emitting device according to claim 1, wherein, The p-type dopant includes at least one selected from quinone derivatives, metal oxides, and cyano-containing compounds.
6. The organic light-emitting device according to claim 1, wherein, The first hole transport layer is located on the first electrode, and The transmitting layer is located on the second hole transport layer.
7. The organic light-emitting device according to claim 6, wherein, The first electrode and the first hole transport layer are in direct contact with each other, and The first hole transport layer and the second hole transport layer are in direct contact with each other.
8. The organic light-emitting device according to claim 1, wherein, The highest occupied molecular orbital (HOMO) level of the host compound in the emitter layer EM1 And the highest occupied molecular orbital energy level (HOMO) of the dopant compound EM2 Satisfying Formula 2: Formula 2 0.1 eV < | |HOMO EM1 | - |Homo EM2 | | < 0.9 eV.
9. The organic light-emitting device according to claim 1, wherein, The main compounds are selected from compounds 1-1 to 1-143: 。 10. The organic light-emitting device according to claim 1, wherein, The dopant compound is selected from the following compounds: 。 11. The organic light-emitting device according to claim 1, wherein, Both the first hole transport compound and the second hole transport compound are independently selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4”-tris(N-carbazolyl)triphenylamine, polyaniline / dodecylbenzenesulfonic acid, poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphorsulfonic acid, polyaniline / poly(4-styrenesulfonate) (PANI / PSS) or combinations thereof: 。 12. The organic light-emitting device according to claim 1, wherein, Both the first hole transport compound and the second hole transport compound are independently selected from compounds HT1 to HT39: 。 13. The organic light-emitting device according to claim 1, wherein, The emitting layer emits blue light with a maximum emission wavelength of 410 nm to 490 nm.
14. The organic light-emitting device according to claim 1, wherein, The emitter layer includes doped and undoped regions. The doped region includes the host compound and the dopant compound, and The undoped region includes the host compound but excludes the dopant compound.
15. The organic light-emitting device according to claim 1, wherein, The first electrode is the anode. The second electrode is the cathode. The organic layer further includes an electron transport region located between the emitter layer and the second electrode, and The electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
16. The organic light-emitting device according to claim 15, wherein, The electron transport region includes metallic materials.
17. The organic light-emitting device according to claim 1, further comprising a capping layer located on the second electrode. in, The capping layer has a refractive index of 1.6 or greater.
18. An apparatus comprising a thin-film transistor and an organic light-emitting device according to claim 1, wherein, The first electrode of the organic light-emitting device is in electrical contact with one of the source electrode and the drain electrode of the thin-film transistor.