Light-emitting device and electronic device including the light-emitting device
By optimizing the hole transport region with specific energy level and dipole moment conditions in an organic light-emitting device, the device's capacitance and light-emitting characteristics are enhanced, addressing turn-on and bleeding issues.
Patent Information
- Application Number
- JP2024232669
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-12-23
- Filing Date
- 2024-12-27
- Publication Date
- 2025-07-10
AI Technical Summary
Existing organic light-emitting devices face challenges in improving capacitance characteristics and light-emitting characteristics, particularly in the low gray-scale region, leading to issues such as turn-on prevention and bleeding.
The introduction of a light-emitting device with specific energy level and dipole moment conditions for the hole transport region, utilizing an organometallic compound with a transition metal and a host compound, to enhance hole mobility and prevent hole accumulation, thereby improving capacitance and light-emitting characteristics.
The proposed device achieves improved capacitance and light-emitting characteristics in the low gray-scale region, preventing turn-on issues and bleeding, resulting in a high-quality electronic device.
Smart Images

Figure 2025105590000001_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to a light-emitting element and an electronic device including the light-emitting element.
Background Art
[0002] Among light-emitting elements, an organic light-emitting device is a self-luminous element. Compared with conventional elements, it has a wide viewing angle, excellent contrast, fast response time, excellent characteristics of luminance, driving voltage, and response speed, and can be multi-colored.
[0003] According to an example, an organic light-emitting device includes an anode, a cathode, and an intermediate layer interposed between the anode and the cathode and including a light-emitting layer. A hole transport region is provided between the anode and the light-emitting layer, and an electron transport region is provided between the light-emitting layer and the cathode. Holes injected from the anode move to the light-emitting layer via the hole transport region, and electrons injected from the cathode move to the light-emitting layer via the electron transport region. The holes and the electrons recombine in the light-emitting layer region to generate excitons. Light is generated while the excitons change from an excited state to a ground state.
Summary of the Invention
Problems to be Solved by the Invention
[0004] By providing a light-emitting element with improved capacitance characteristics and improved light-emitting characteristics in a low gray-scale region, a high-quality electronic device using the same can be realized.
Means for Solving the Problems
[0005] According to one aspect, a first electrode, a second electrode facing the first electrode, and an intermediate layer disposed between the first electrode and the second electrode, wherein the intermediate layer includes a light-emitting layer and a hole transport region, The positive hole transport region includes a first layer, The first layer is disposed between the first electrode and the light-emitting layer, The light-emitting layer includes a host and an organometallic compound, The organometallic compound includes a transition metal, The host includes a first compound, The first layer includes a first material, There is provided a light-emitting device that satisfies the following <Condition 1> or <Condition 2>: <Condition 1> ΔHOMO is less than 0 eV, and the dipole moment of the first material is less than 3.0 debye, <Condition 2> ΔHOMO is greater than 0 eV, and the dipole moment of the first material is 3.0 debye or more, In the above <Condition 1> and <Condition 2>, The ΔHOMO is a value obtained by subtracting the HOMO energy level of the first compound from the HOMO energy level of the first material, The HOMO energy level of the first compound, the HOMO energy level of the first material, and the dipole moment of the first material are each calculated based on the Density Functional Theory (DFT), The HOMO energy level of the first compound and the HOMO energy level of the first material are negative numbers.
[0006] According to another aspect, there is provided an electronic device including the light-emitting device.
Advantages of the Invention
[0007] The light-emitting device has improved capacitance characteristics and improved light-emitting characteristics in the low gray scale region, and a high-quality electronic device can be manufactured by utilizing this.
Brief Description of the Drawings
[0008]
Figure 1
Figure 2
Embodiments for Carrying Out the Invention
[0009] The light-emitting device includes a first electrode, a second electrode facing the first electrode, and an intermediate layer disposed between the first electrode and the second electrode, and the intermediate layer includes a light-emitting layer and a hole transport region.
[0010] In this specification, "intermediate layer" is a term indicating a single and / or multiple layers disposed between the first electrode and the second electrode in a light-emitting device. The "intermediate layer" includes not only organic compounds but also organometallic complexes containing metals.
[0011] The hole transport region is disposed between the first electrode and the light-emitting layer.
[0012] For example, the first electrode is a hole injection electrode or an anode, and the second electrode is an electron injection electrode or a cathode.
[0013] The hole transport region includes a first layer, and the first layer is disposed between the first electrode and the light-emitting layer. The hole transport region may further include, in addition to the first layer, a hole injection layer, a hole transport layer, an electron blocking layer, an auxiliary layer, or any combination thereof.
[0014] According to an embodiment, the first layer can be in direct contact with the light-emitting layer.
[0015] The light-emitting device may further include an electron transport region disposed between the light-emitting layer and the second electrode. The electron transport region may include a buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0016] The light-emitting layer includes a host and an organometallic compound. The organometallic compound contains a transition metal.
[0017] The host includes a first compound. When the host further includes an additional compound other than the first compound, the HOMO energy level of the first compound is higher than the HOMO energy level of the additional compound contained in the host. That is, the first compound is a compound having the largest (or highest) HOMO energy level among the compounds contained in the host.
[0018] The first layer includes a first substance.
[0019] The first compound contained in the light-emitting layer and the first substance contained in the first layer are different from each other.
[0020] For the descriptions of the first compound and the organometallic compound contained in the light-emitting layer, and the first substance contained in the first layer, refer to what is described in this specification.
[0021] The light-emitting element can satisfy the following <Condition 1> or <Condition 2>: <Condition 1> ΔHOMO is less than 0 eV and the dipole moment of the first substance is less than 3.0 debye. <Condition 2> ΔHOMO is greater than 0 eV and the dipole moment of the first substance is 3.0 debye or more.
[0022] The ΔHOMO is a value obtained by subtracting the HOMO energy level of the first compound from the HOMO energy level of the first substance. That is, the ΔHOMO is "the HOMO energy level of the first substance - the HOMO energy level of the first compound", has the unit of "eV", and is a negative or positive number.
[0023] The HOMO energy level of the first compound, the HOMO energy level of the first substance, and the dipole moment of the first substance are each calculated based on density functional theory (DFT), and the HOMO energy level of the first compound and the HOMO energy level of the first substance are each negative. For example, the HOMO energy level of the first compound, the HOMO energy level of the first substance, and the dipole moment of the first substance are each evaluated using the DFT method (T1 adiabatic) of the Gaussian program with structural optimization at the B3LYP / 6-31G(d,p) level as described in Evaluation 1.
[0024] On the other hand, when the host further contains an additional compound other than the first compound, the HOMO energy level of the additional compound is also a negative number calculated based on density functional theory (DFT). For example, the HOMO energy level of the additional compound is a negative number evaluated using the DFT method (T1 adiabatic) of the Gaussian program with structural optimization at the B3LYP / 6-31G(d,p) level as described in Evaluation 1.
[0025] In this specification, each of the HOMO energy level and the LUMO energy level is a negative number calculated based on density functional theory (DFT).
[0026] In this specification, the HOMO energy level, the LUMO energy level, the dipole moment, and the triplet (T1) energy of various compounds are each calculated based on density functional theory (DFT), and are evaluated using the DFT method (T1 adiabatic) of the Gaussian program with structural optimization at the B3LYP / 6-31G(d,p) level as described in Evaluation 1, for example.
[0027] The holes injected from the first electrode are transmitted to the light-emitting layer through the hole transport region. Since the accumulation of holes inside the light-emitting layer and / or at the interface between the light-emitting layer and the hole transport region during the driving of the light-emitting device causes a decrease in the light-emitting efficiency and / or lifetime of the light-emitting device, it is necessary to improve the capacitance of the light-emitting device to prevent this.
[0028] When ΔHOMO of the light-emitting device is less than 0 eV as in the <Condition 1>, that is, when the HOMO energy level of the first substance contained in the first layer is less than the HOMO energy level of the first compound contained in the light-emitting layer (or when the HOMO energy level of the first substance contained in the first layer is deeper than the HOMO energy level of the first compound contained in the light-emitting layer), the injection of holes from the first electrode into the light-emitting layer is not relatively smoothly performed. Here, if the dipole moment of the first substance contained in the first layer is adjusted to be less than 3.0 debye, which is a relatively small value as in the <Condition 1>, and the energetic disorder of the first layer is relatively decreased, the hole mobility in the first layer increases. Therefore, the accumulation of holes inside the light-emitting layer and / or at the interface between the light-emitting layer and the hole transport region during the driving of the light-emitting device can be substantially prevented.
[0029] On the other hand, when ΔHOMO of the light-emitting device is greater than 0 eV as in the <Condition 2>, that is, when the HOMO energy level of the first substance contained in the first layer is greater than the HOMO energy level of the first compound contained in the light-emitting layer (or when the HOMO energy level of the first substance contained in the first layer is shallower than the HOMO energy level of the first compound contained in the light-emitting layer), the injection of holes from the first electrode into the light-emitting layer is relatively smoothly performed. Here, if the dipole moment of the first substance contained in the first layer is adjusted to be 3.0 debye or more, which is a relatively large value as in the <Condition 2>, and the energetic disorder of the first layer is relatively increased, the hole mobility in the first layer decreases. Therefore, the accumulation of holes inside the light-emitting layer and / or at the interface between the light-emitting layer and the hole transport region during the driving of the light-emitting device can be substantially prevented.
[0030] Therefore, when the light-emitting element satisfies the above-described <Condition 1> or <Condition 2>, the accumulation of holes inside the light-emitting layer and / or at the interface between the light-emitting layer and the hole transport region during the driving of the light-emitting element is substantially prevented, and the capacitance characteristics of the light-emitting element are improved. As a result, for example, the improvement of the light-emitting characteristics in the low gradation region of the light-emitting element, such as turn-on prevention and / or bleeding prevention, can be effectively achieved, and a high-quality electronic device can be manufactured using the above-described light-emitting element.
[0031] According to one embodiment, among the values obtained by multiplying the value obtained by subtracting 3 debye from the dipole moment of the first substance by ΔHOMO, the value excluding the unit is a positive number (for example, 0.0 or more and 0.7 or less).
[0032] According to another embodiment, the light-emitting element satisfies the above-described <Condition 1>, and ΔHOMO is -0.5 eV or more and less than 0 eV, -0.5 eV or more and less than -0.001 eV, -0.5 eV or more and less than -0.005 eV, -0.5 eV or more and less than -0.01 eV, -0.5 eV or more and less than -0.052 eV, -0.4 eV or more and less than 0 eV, -0.4 eV or more and less than -0.001 eV, -0.4 eV or more and less than -0.005 eV, -0.4 eV or more and less than -0.01 eV, -0.4 eV or more and less than -0.052 eV, -0.310 eV or more and less than 0 eV, -0.310 eV or more and less than -0.001 eV, -0.310 eV or more and less than -0.005 eV, -0.310 eV or more and less than -0.01 eV, or -0.310 eV or more and less than -0.052 eV.
[0033] According to still other embodiments, the light-emitting element satisfies the <Condition 1>, and the dipole moment of the first substance is 0.5 debye or more and less than 3.0 debye, 0.8 debye or more and less than 3.0 debye, 1.0 debye or more and less than 3.0 debye, 1.2 debye or more and less than 3.0 debye, 1.341 debye or more and less than 3.0 debye, 0.5 debye or more and less than 2.9 debye, 0.8 debye or more and less than 2.9 debye, 1.0 debye or more and less than 2.9 debye, 1.2 debye or more and less than 2.9 debye, 1.341 debye or more and less than 2.9 debye, 0.5 debye or more and less than 2.805 debye, 0.8 debye or more and less than 2.805 debye, 1.0 debye or more and less than 2.805 debye, 1.2 debye or more and less than 2.805 debye, or 1.341 debye or more and less than 2.805 debye.
[0034] According to still other embodiments, the light-emitting element satisfies the <Condition 2>, and ΔHOMO is more than 0 eV and 0.1 eV or less, more than 0 eV and 0.06 eV or less, more than 0 eV and 0.043 eV or less, 0.0001 eV or more and 0.1 eV or less, 0.0001 eV or more and 0.06 eV or less, 0.0001 eV or more and 0.043 eV or less, 0.001 eV or more and 0.1 eV or less, 0.001 eV or more and 0.06 eV or less, or 0.001 eV or more and 0.043 eV or less.
[0035] According to still other embodiments, the light-emitting element satisfies the <Condition 2>, and the dipole moment of the first substance is 3.0 debye or more and 6.0 debye or less, 3.0 debye or more and 5.0 debye or less, 3.0 debye or more and 4.667 debye or less, 3.5 debye or more and 6.0 debye or less, 3.5 debye or more and 5.0 debye or less, 3.5 debye or more and 4.667 debye or less, 4.0 debye or more and 6.0 debye or less, 4.0 debye or more and 5.0 debye or less, or 4.0 debye or more and 4.667 debye or less.
[0036] According to still other embodiments, the HOMO energy level of the first compound included in the light-emitting layer is -5.6 eV to -4.8 eV, -5.6 eV to -4.9 eV, -5.6 eV to -5.0 eV, -5.5 eV to -4.8 eV, -5.5 eV to -4.9 eV, -5.5 eV to -5.0 eV, -5.4 eV to -4.8 eV, -5.4 eV to -4.9 eV, -5.4 eV to -5.07 eV, or -5.419 eV to -5.066 eV.
[0037] According to still other embodiments, the triplet (T1) energy level of the first compound included in the light-emitting layer is 2.8 eV or higher, 2.8 eV to 3.5 eV, 2.8 eV to 3.3 eV, 2.8 eV to 3.1 eV, 2.8 eV to 3.05 eV, or 2.81 eV to 3.05 eV.
[0038] According to still other embodiments, the HOMO energy level of the first substance included in the first layer is -5.6 eV to -4.8 eV, -5.6 eV to -4.9 eV, -5.6 eV to -5.0 eV, -5.5 eV to -4.8 eV, -5.5 eV to -4.9 eV, -5.5 eV to -5.0 eV, -5.4 eV to -4.8 eV, -5.4 eV to -4.9 eV, -5.4 eV to -5.07 eV, or -5.419 eV to -5.066 eV.
[0039] According to still other embodiments, the dipole moment of the first substance included in the first layer is 0.8 debye to 7.0 debye, 0.8 debye to 6.0 debye, 0.8 debye to 5.1 debye, 1.0 debye to 6.0 debye, 1.0 debye to 5.1 debye, 1.2 debye to 6.0 debye, 1.2 debye to 5.1 debye, 1.3 debye to 6.0 debye, 1.3 debye to 5.1 debye, or 1.341 debye to 5.008 debye.
[0040] According to still other embodiments, each of the first compound included in the light-emitting layer and the first substance included in the first layer has at least one π-electron-excessive C3-C 60A compound that contains a cyclic group (e.g., a carbazole group, an indolocarbazole group, a benzene group, etc.) and does not contain an electron-transporting moiety. Examples of the electron-transporting moiety include a cyano group, a fluoro group, a nitrogen-containing C1-C π-electron-deficient 60 A cyclic group (e.g., a triazine group, a pyrimidine group, etc.), a phosphine oxide group, a sulfoxide group, etc. are included.
[0041] According to still other embodiments, each of the first compound included in the light-emitting layer and the first substance included in the first layer may contain at least one carbazole group, at least one deuterium, at least one tert-butyl group, at least one silicon, or any combination thereof.
[0042] According to still other embodiments, the first compound included in the light-emitting layer contains at least one silicon.
[0043] According to still other embodiments, the first substance included in the first layer does not contain silicon.
[0044] According to still other embodiments, each of the first compound included in the light-emitting layer and the first substance included in the first layer does not contain an amine moiety.
[0045] According to still other embodiments, the transition metal of the organometallic compound is iridium (Ir), platinum (Pt), palladium (Pd), gold (Au), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).
[0046] According to still other embodiments, the organometallic compound contained in the light-emitting layer further includes n ligands bonded to the transition metal, where n is an integer from 1 to 4. Each of the ligands is a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, or the like.
[0047] According to still other embodiments, the organometallic compound contained in the light-emitting layer further includes n ligands bonded to the transition metal, the transition metal in the organometallic compound is platinum (Pt) or palladium (Pd), n is 1, and the ligand is a tetradentate ligand.
[0048] According to still other embodiments, the tetradentate ligand includes a carbene moiety bonded to the transition metal.
[0049] According to still other embodiments, the organometallic compound contained in the light-emitting layer further includes n ligands bonded to the transition metal, the transition metal in the organometallic compound is iridium (Ir) or osmium (Os), n is 3, and at least one of the n ligands is a bidentate ligand containing -F, a cyano group, or a combination thereof, or a bidentate ligand containing a carbene moiety bonded to the transition metal. For example, the bidentate ligand may further include an imidazole group or a triazole group.
[0050] According to still other embodiments, the HOMO energy level of the organometallic compound is -4.1 eV to -5.1 eV, -4.1 eV to -4.9 eV, -4.1 eV to -4.7 eV, -4.3 eV to -5.1 eV, -4.3 eV to -4.9 eV, or -4.3 eV to -4.7 eV.
[0051] According to still other embodiments, the dipole moment of the organometallic compound is 4.0 debye to 12.0 debye, 4.0 debye to 10.0 debye, 4.0 debye to 8.0 debye, 6.0 debye to 12.0 debye, 6.0 debye to 10.0 debye, 6.0 debye to 8.0 debye, 7.0 debye to 12.0 debye, 7.0 debye to 10.0 debye, or 7.0 debye to 8.0 debye.
[0052] According to still other embodiments, the T1 energy of the organometallic compound is 2.2 eV to 3.0 eV, 2.2 eV to 2.8 eV, 2.2 eV to 2.7 eV, 2.4 eV to 3.0 eV, 2.4 eV to 2.8 eV, 2.4 eV to 2.7 eV, 2.6 eV to 3.0 eV, 2.6 eV to 2.8 eV, or 2.6 eV to 2.7 eV.
[0053] According to still other embodiments, the organometallic compound is an organometallic compound represented by Chemical Formula 3 (Chemical Formula 24) and / or an organometallic compound represented by Chemical Formula 5 (Chemical Formula 31) described herein. Descriptions regarding Chemical Formulas 3 and 5 will be described later.
[0054] According to still other embodiments, the content (by weight) of the host in the light-emitting layer is 50 parts by weight or more, 50 parts by weight to 99 parts by weight, or 60 parts by weight to 95 parts by weight per 100 parts by weight of the light-emitting layer.
[0055] According to still other embodiments, the host of the light-emitting layer further contains a second compound, and the second compound is different from the first compound. That is, the additional compound contains the second compound.
[0056] According to still other embodiments, the host of the light-emitting layer further contains a second compound, the second compound is different from the first compound, and the HOMO energy level of the first compound is greater than (or higher than) the HOMO energy level of the second compound.
[0057] According to still other embodiments, the host of the light-emitting layer contains only a first compound, and the first compound is a hole-transporting compound, an electron-transporting compound, or an ambipolar compound.
[0058] According to still other embodiments, the host of the light-emitting layer further contains a second compound, the second compound is different from the first compound, the first compound is a hole-transporting compound, and the second compound is an electron-transporting compound.
[0059] According to still other embodiments, the first compound is a compound that contains at least one π-electron-excessive C3-C 60 cyclic group (e.g., a carbazole group, an indolocarbazole group, a benzene group, etc.) and does not contain an electron-transporting moiety. Examples of the electron-transporting moiety include a cyano group, a fluoro group, a π-electron-deficient nitrogen-containing C1-C 60 cyclic group (e.g., a triazine group, a pyrimidine group, etc.), a phosphine oxide group, a sulfoxide group, etc.
[0060] According to still other embodiments, the second compound is a compound that contains at least one electron-transporting moiety. The electron-transporting moiety is a cyano group, a fluoro group, a π-electron-deficient nitrogen-containing C1-C 60 cyclic group (e.g., a triazine group, a pyrimidine group, etc.), a phosphine oxide group, a sulfoxide group, or any combination thereof.
[0061] According to still other embodiments, the second compound contains an azine group (e.g., a triazine group, etc.).
[0062] According to still other embodiments, the second compound a triazine group; and may contain at least one carbazole group, at least one deuterium, at least one tert-butyl group, at least one silicon, or any combination thereof.
[0063] According to still other embodiments, the triplet (T1) energy level of the second compound is in the range of 2.3 eV to 3.5 eV, 2.4 eV to 3.2 eV, 2.5 eV to 3.1 eV, or 2.6 eV to 3.0 eV.
[0064] According to still other embodiments, the LUMO energy level of the second compound is -2.2 eV to -1.4 eV, -2.0 eV to -1.4 eV, -1.8 eV to -1.4 eV, -2.2 eV to -1.6 eV, -2.0 eV to -1.6 eV, or -1.8 eV to -1.6 eV.
[0065] When the host of the light-emitting layer further contains a second compound, the weight ratio of the first compound to the second compound is in the range of 1:99 to 99:1, 10:90 to 90:10, 20:80 to 80:20, 30:70 to 70:30, or 40:60 to 60:40. When the weight ratio of the first compound to the second compound satisfies the above range, the balance between holes and electrons in the light-emitting layer is effectively achieved, and a light-emitting device having excellent luminous efficiency and / or lifetime characteristics can be realized.
[0066] According to still other embodiments, the light-emitting layer can emit blue light.
[0067] According to still other embodiments, the light-emitting layer can emit light (e.g., blue light) having a maximum emission wavelength range in the range of 400 nm to 490 nm, 410 nm to 470 nm, or 420 nm to 450 nm.
[0068] A light-emitting device in which the organometallic compound is an emitter The organometallic compound contained in the light-emitting layer is an emitter (or can serve as an emitter). That is, the organometallic compound is a compound that can transfer excitons generated from the host and emit light by transitioning to the ground state therefrom.
[0069] For example, the light-emitting layer includes a non-emissive material and an emitter, and the host is included in the non-emissive material.
[0070] The organometallic compound can emit phosphorescence or fluorescence (e.g., delayed fluorescence).
[0071] The content (by weight) of the organometallic compound is in the range of 0.01 part by weight to 30 parts by weight per 100 parts by weight of the light-emitting layer.
[0072] According to one embodiment, the organometallic compound included in the light-emitting layer can emit blue light.
[0073] According to other embodiments, the organometallic compound included in the light-emitting layer can emit light (e.g., blue light) having a maximum emission wavelength range in the range of 400 nm to 490 nm, 410 nm to 470 nm, or 420 nm to 450 nm.
[0074] A light-emitting device further comprising a thermally activated delayed fluorescence substance For example, the light-emitting layer may further include a thermally activated delayed fluorescence material.
[0075] According to one embodiment, the thermally activated delayed fluorescence material included in the light-emitting layer is an emitter (or can serve as an emitter), and the organometallic compound included in the light-emitting layer is a sensitizer (or can serve as a sensitizer). Therefore, the light-emitting device is a fluorescent light-emitting device. The sensitizer can effectively transfer excitons formed from the non-emissive material included in the light-emitting layer to the emitter.
[0076] According to other embodiments, the thermally activated delayed fluorescence material included in the light-emitting layer is a sensitizer (or can serve as a sensitizer), and the organometallic compound included in the light-emitting layer is an emitter (or can serve as an emitter).
[0077] According to still other embodiments, the thermally activated delayed fluorescence material is a multiple resonance thermally activated delayed fluorescence material. The multiple resonance thermally activated delayed fluorescence material does not contain a transition metal and is a polycyclic compound containing a core in which two or more C3-C 60 cyclic groups are condensed with each other, and two C3-C 60 cyclic groups among the cores are condensed with each other while sharing boron (B) or nitrogen (N).
[0078] According to still other embodiments, the emitter is a polycyclic compound represented by the following Chemical Formula 4 (Chemical Formula 36). The description regarding Chemical Formula 4 will be provided later.
[0079] According to still other embodiments, the content (by weight) of the thermally activated delayed fluorescence material is 0.01 part by weight to 30 parts by weight per 100 parts by weight of the light-emitting layer.
[0080] According to still other embodiments, the thermally activated delayed fluorescence material contained in the light-emitting layer can emit blue light.
[0081] According to still other embodiments, the thermally activated delayed fluorescence material contained in the light-emitting layer can emit light (for example, blue light) having a maximum emission wavelength range in the range of 400 nm to 490 nm, 410 nm to 470 nm, or 420 nm to 450 nm.
[0082] According to still other embodiments, at least one of the first substance, the first compound, and the organometallic compound, and optionally, at least one of the second compound and the thermally activated delayed fluorescence material contains at least one deuterium.
[0083] Hereinafter, each chemical formula will be described.
[0084] Explanation regarding Chemical Formulas 1-1, 1-2, and 1-3 In this specification, each of the first substance contained in the first layer and the first compound contained in the light-emitting layer is a compound represented by the following Chemical Formula 1-1 (Chemical Formula 1), a compound represented by the following Chemical Formula 1-2 (Chemical Formula 2), a compound represented by the following Chemical Formula 1-3 (Chemical Formula 3), or a combination thereof.
[0085]
Chem.
[0086]
Chem.
[0087]
Chem.
[0088]
Chem.
[0089] In Chemical Formulas 1-1, 1-2, and 1-3, R1 to R7 are, independently of one another, a group represented by the following Chemical Formula S-1 (Chemical Formula 4); hydrogen, deuterium, C1-C 60 alkyl group, deuterated C1-C 60 alkyl group, C1-C 60 alkoxy group, or deuterated C1-C 60 alkoxy group; or deuterium, C1-C 60 alkyl group, C1-C 60 alkoxy group, a π-electron-excessive C5-C 60 cyclic group, or a substituted or unsubstituted π-electron-excessive C5-C 60 cyclic group; and in Chemical Formulas 1-1, 1-2, and 1-3, a1 to a7 are, independently of one another, integers from 1 to 20, In Chemical Formulas 1-1, 1-2, 1-3, and S-1, each of Ring A1 to Ring A7 and Ring B1 to Ring B4 is a π-electron-excessive C5-C 60 cyclic group, In Chemical Formulas 1-1, 1-2, 1-3, and S-1, m1 and m2 are each independently 0, 1, 2, or 3. i) When m1 is 0, the group represented by the following Chemical Formula 5 is a single bond. ii) When m2 is 0, the group represented by the following Chemical Formula 6 is a single bond. In Chemical Formula S-1, W1 to W4 are each independently hydrogen, deuterium, a C1-C 60 alkyl group, a deuterated C1-C 60 alkyl group, a C1-C 60 alkoxy group, or a deuterated C1-C 60 alkoxy group; or deuterium, a C1-C 60 alkyl group, a C1-C 60 alkoxy group, a π-electron-excessive C5-C 60 cyclic group, or a π-electron-excessive C5-C 60 cyclic group which is substituted or unsubstituted with any combination thereof; In Chemical Formula S-1, b1 to b4 are each independently an integer from 1 to 20.
[0090]
Chemical Formula
[0091]
Chemical Formula
[0092] According to one embodiment, at least one of R1, R2, R3, R4, R5, and R6 in Chemical Formula 1-1, at least one of R1, R2, R4, R5, and R6 in Chemical Formula 1-2, and at least one of R1, R2, R3, R4, R5, R6, and R7 in Chemical Formula 1-3 are groups represented by Chemical Formula S-1.
[0093] According to another embodiment, in Chemical Formulas 1-1, 1-2, and 1-3, each of R1 to R7 is not a group represented by Chemical Formula S-1.
[0094] According to still another embodiment, in Chemical Formulas 1-1, 1-2, and 1-3, R1 to R7 are, independently of one another, a group represented by Chemical Formula S-1; hydrogen, deuterium, C1-C 20 alkyl group, deuterated C1-C 20 alkyl group, C1-C 20 alkoxy group, or deuterated C1-C 20 alkoxy group; or deuterium, C1-C 20 alkyl group, deuterated C1-C 20 alkyl group, C1-C 20 alkoxy group, deuterated C1-C 20 alkoxy group, phenyl group, deuterated phenyl group, biphenyl group, deuterated biphenyl group, terphenyl group, deuterated terphenyl group, naphthyl group, furanyl group, thiophenyl group, pyrrolyl group, cyclopentadienyl group, silolyl group, benzofuranyl group, benzothiophenyl group, indolyl group, indenyl group, benzosilolyl group, dibenzofuranyl group, deuterated dibenzofuranyl group, dibenzothiophenyl group, deuterated dibenzothiophenyl group, carbazolyl group, deuterated carbazolyl group, fluorenyl group, dibenzosilolyl group, benzofluorocarbazolyl group, benzothienocarbazolyl group, indolocarbazolyl group, indenocarbazolyl group, benzosilolocarbazolyl group, or a benzene group, naphthalene group, furan group, thiophene group, pyrrole group, cyclopentadiene group, silole group, benzofuran group, benzothiophene group, indole group, indene group, benzosilole group, dibenzofuran group, dibenzothiophene group, carbazole group, fluorene group, dibenzosilole group, benzofluorocarbazole group, benzothienocarbazole group, indolocarbazole group, indenocarbazole group, or benzosilolocarbazole group, which is substituted or unsubstituted with any combination thereof;
[0095] According to still other embodiments, in Chemical Formulas 1-1, 1-2, and 1-3, R1 to R7 are each independently a group represented by Chemical Formula S-1; hydrogen, deuterium, C1-C 20 alkyl group, or deuterated C1-C 20 alkyl group; or deuterium, C1-C 20 alkyl group, deuterated C1-C 20 alkyl group, phenyl group, deuterated phenyl group, biphenyl group, deuterated biphenyl group, terphenyl group, deuterated terphenyl group, dibenzofuranyl group, deuterated dibenzofuranyl group, dibenzothiophenyl group, deuterated dibenzothiophenyl group, carbazolyl group, deuterated carbazolyl group, or a benzene group, dibenzofuran group, dibenzothiophene group, carbazole group, benzofluorocarbazole group, benzothienocarbazole group, or indolocarbazole group which is substituted or unsubstituted with any combination thereof;
[0096] According to still other embodiments, in Chemical Formula 1-1, i) R1, ii) R3, iii) R4, or iv) each of R3 and R4 is a group represented by Chemical Formula S-1.
[0097] According to still other embodiments, in Chemical Formula 1-2, R6 is a group represented by Chemical Formula S-1.
[0098] On the other hand, in Chemical Formulas 1-1, 1-2, 1-3, and S-1, Ring A1 to Ring A7 and Ring B1 to Ring B4 are each independently a benzene group, naphthalene group, furan group, thiophene group, pyrrole group, cyclopentadiene group, silole group, benzofuran group, benzothiophene group, indole group, indene group, benzosilole group, dibenzofuran group, dibenzothiophene group, carbazole group, fluorene group, dibenzosilole group, benzofluorocarbazole group, benzothienocarbazole group, indolocarbazole group, indenocarbazole group, or benzosilolocarbazole group.
[0099] According to one embodiment, the rings A1, A2, A4, and A5 are, independently of one another, a benzene group, a benzofuran group, a benzothiophene group, or an indole group.
[0100] According to another embodiment, the rings A3, A6, A7, and rings B1 to B4 are, independently of one another, a benzene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a benzofluorocarbazole group, a benzothienocarbazole group, or an indolocarbazole group.
[0101] In the chemical formula S-1, W1 to W4 are, independently of one another, hydrogen, deuterium, C1-C 20 alkyl group, deuterated C1-C 20 alkyl group, C1-C 20 alkoxy group, or deuterated C1-C 20 alkoxy group; or deuterium, C1-C 20 alkyl group, deuterated C1-C 20 alkyl group, C1-C 20 alkoxy group, deuterated C1-C 20An alkoxy group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a naphthyl group, a furanyl group, a thiophenyl group, a pyrrolyl group, a cyclopentadienyl group, a silolyl group, a benzofuranyl group, a benzothiophenyl group, an indolyl group, an indenyl group, a benzosilolyl group, a dibenzofuranyl group, a deuterated dibenzofuranyl group, a dibenzothiophenyl group, a deuterated dibenzothiophenyl group, a carbazolyl group, a deuterated carbazolyl group, a fluorenyl group, a dibenzosilolyl group, a benzofluorocarbazolyl group, a benzothienocarbazolyl group, an indolocarbazolyl group, an indenocarbazolyl group, a benzosilolocarbazolyl group, or a benzene group, a naphthalene group, a furan group, a thiophene group, a pyrrole group, a cyclopentadiene group, a silole group, a benzofuran group, a benzothiophene group, an indole group, an indene group, a benzosilole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, a benzofluorocarbazole group, a benzothienocarbazole group, an indolocarbazole group, an indenocarbazole group, or a benzosilolocarbazole group which is substituted or unsubstituted with any combination thereof; provided that.
[0102] Specific examples of the first compound contained in the light-emitting layer and the first substance contained in the first layer According to one embodiment, the first compound contained in the light-emitting layer and the first substance contained in the first layer are independently selected from the following compounds H1 to H108 (Chemical Formulas 7 to 15) and their deuterium-containing derivatives.
[0103] As used herein, the term "deuterium-containing derivative" means a compound having the same backbone as the backbone of the compound, but at least one of the hydrogens of the compound is substituted with deuterium, or the substitution position of the deuterium contained in the compound is changed.
[0104] According to another embodiment, the first compound contained in the light-emitting layer is selected from the following compounds H1 to H42 and their deuterium-containing derivatives.
[0105] According to still other embodiments, the first compound contained in the light-emitting layer is selected from the following compounds H2 to H14 and H43 to H108 and their deuterium-containing derivatives.
[0106] According to still other embodiments, the first substance contained in the first layer is selected from the following compounds H2 to H14 and H43 to H108 and their deuterium-containing derivatives.
[0107] According to still other embodiments, when the first compound contained in the light-emitting layer is the following compound H1, the first substance contained in the first layer may be selected from the following compounds H5 to H108 and their deuterium-containing derivatives.
[0108]
Chemical formula
[0109]
Chemical formula
[0110]
Chemical formula
[0111]
Chemical formula
[0112]
Chemical formula
[0113]
Chemical formula
[0114]
Chemical formula
[0115] [Chemistry]
[0116] [Chemistry]
[0117] Explanation regarding Chemical Formula 2 In this specification, the second compound contained in the light-emitting layer is a compound represented by the following Chemical Formula 2 (Chemical Formula 16).
[0118] [Chemistry]
[0119] In Chemical Formula 2, X4 is N, C(H), or C(Z 14 ), X5 is N, C(H), or C(Z 15 ), and X6 is N, C(H), or C(Z 16 ), but at least one of X4 to X6 is N, Z1 to Z3 are, independently of one another, *-Si(Ar1)(Ar2)-*’, a C5-C 30 carbocyclic group which is substituted or unsubstituted with at least one R0, or a C2-C 30 heterocyclic group which is substituted or unsubstituted with at least one R0, e1 to e3 are, independently of one another, 0, 1, 2, or 3, and i) when e1 is 0, the group represented by *-(Z1) e1 -*’ is a single bond, ii) when e2 is 0, the group represented by *-(Z2) e2 -*’ is a single bond, and iii) when e3 is 0, the group represented by *-(Z3) e3 -*’ is a single bond, Z 11 ~Z 13 are, independently of one another, *-Si(Ar 11 )(Ar 12 )(Ar 13)、 at least one R0 - substituted or unsubstituted C5 - C 30 carbocyclic group, or at least one R0 - substituted or unsubstituted C2 - C 30 heterocyclic group, and Ar1, Ar2 and Ar 11 ~Ar 13 are, independently of one another, at least one R0 - substituted or unsubstituted C5 - C 30 carbocyclic group, or at least one R0 - substituted or unsubstituted C2 - C 30 heterocyclic group, and said R0 and Z 14 ~Z 16 are, independently of one another, deuterium, a C1 - C 60 alkyl group, or a deuterated C1 - C 60 alkyl group; or deuterium, a C1 - C 60 alkyl group, a deuterated C1 - C 60 alkyl group, a C5 - C 30 carbocyclic group, a C2 - C 30 heterocyclic group, or a C5 - C 30 carbocyclic group or a C2 - C 30 heterocyclic group; substituted or unsubstituted with any combination thereof.
[0120] For example, in Chemical Formula 2 above, at least two of X4 to X6 are N.
[0121] As yet another example, in Chemical Formula 2 above, X4 to X6 are all N.
[0122] According to one embodiment, said Z1 to Z3 are, independently of one another, * - Si(Ar1)(Ar2)-* ', a benzene group substituted or unsubstituted with at least one R0, or a carbazole group substituted or unsubstituted with at least one R0.
[0123] According to another embodiment, said Z1 to Z3 are, independently of one another, a group represented by one of the following Chemical Formulas 2(1) to 2(3) (Chemical Formula 17).
[0124] [Chemical formula]
[0125] In the above chemical formulas 2(1) to 2(3), Refer to the description of R0 as described in this specification. c4 is an integer from 0 to 4. Each of * and *’ is a bonding site with an adjacent atom.
[0126] According to still another embodiment, the Z1 to Z3 are, independently of each other, groups represented by one of the chemical formulas 2(2) and 2(3).
[0127] According to still another embodiment, in the chemical formula 2, i) e1 is 1, 2, or 3, and each of e2 and e3 is 0, or ii) e1 and e2 are, independently of each other, 1, 2, or 3, and e3 is 0, or iii) e1, e2, and e3 are, independently of each other, 1, 2, or 3.
[0128] According to still another embodiment, the Z 11 ~Z 13 are, independently of each other, *-Si(Ar 11 )(Ar 12 )(Ar 13 ); or Deuterium, a C1-C 20 alkyl group, a phenyl group, an N-carbazolyl group, or a phenyl group or an N-carbazolyl group substituted or unsubstituted with any combination thereof;
[0129] According to still another embodiment, at least one of the Z 11 ~Z 13 is, independently of each other, *-Si(Ar 11 )(Ar 12 )(Ar 13 ); or Deuterium, C1-C 20 an alkyl group, a phenyl group, an N-carbazolyl group, or an N-carbazolyl group which is substituted or unsubstituted with any combination thereof; provided that.
[0130] According to still another embodiment, the Z 11 ~Z 13 at least one of is *-Si(Ar 11 )(Ar 12 )(Ar 13 ), or a group represented by the following Chemical Formula 2-CZ (Formula 18).
[0131]
Chemical Formula
[0132] In the Chemical Formula 2-CZ, the description of R0 refers to that described in this specification, c8 is an integer from 0 to 8, * is a bonding site with an adjacent atom.
[0133] According to still another embodiment, in the Chemical Formula 2, i) each of the Z 11 , Z 12 and Z 13 is identical to each other, or ii) the Z 11 and Z 12 are different from each other, the Z 12 and the Z 13 are identical to each other, or iii) the Z 11 , Z 12 and Z 13 are different from each other.
[0134] According to still another embodiment, the Ar1, Ar2 and Ar 11 ~Ar 13 are, independently of each other, deuterium, C1-C 20It is a phenyl group which is substituted or unsubstituted with an alkyl group, a phenyl group, an N-carbazolyl group, or any combination thereof.
[0135] According to still another embodiment, the R0 and Z 14 ~Z 16 are, independently of each other, deuterium, a C1-C 20 alkyl group, or a deuterated C1-C 20 alkyl group; or deuterium, a C1-C 20 alkyl group, a phenyl group, an N-carbazolyl group, or a phenyl group or an N-carbazolyl group which is substituted or unsubstituted with any combination thereof;
[0136] According to another embodiment, the second compound is a compound represented by the following Chemical Formula 2-1 (Formula 19) or 2-2 (Formula 20).
[0137]
Chemical formula
[0138]
Chemical formula
[0139] In the Chemical Formulas 2-1 and 2-2, the descriptions of Z1, Z2, e1, e2 and Z 11 are the same as those described herein, Z 22 and Z 23 the descriptions of each refer to the description of R0 in this specification, e23 and e22 are, independently of each other, integers from 0 to 8, Ar 21 , Ar 22 and Ar 23 the descriptions of each refer to the descriptions of Ar 11 , Ar 12 and Ar 13 in this specification respectively.
[0140] According to still other embodiments, in Chemical Formula 2-1, e2 is not 0.
[0141] According to still other embodiments, the second compound is represented by Chemical Formula 2-1 or 2-2 and can satisfy at least one of the following <Condition 11> to <Condition 13>: <Condition 11> In Chemical Formulas 2-1 and 2-2, Z 11 is a phenyl group or an N-carbazolyl group which is substituted or unsubstituted with deuterium, a C1-C 20 alkyl group, a phenyl group, an N-carbazolyl group, or any combination thereof. <Condition 12> In Chemical Formulas 2-1 and 2-2, Z 11 is *-Si(Ar 11 )(Ar 12 )(Ar 13 ). <Condition 13> In Chemical Formulas 2-1 and 2-2, Z1 and Z2 are, independently of each other, an o-phenylene group or an m-phenylene group which is substituted or unsubstituted with deuterium, a C1-C 20 alkyl group, a phenyl group, an N-carbazolyl group, or any combination thereof.
[0142] According to still other embodiments, the second compound can satisfy at least one of the following <Condition 14> and <Condition 15>: <Condition 14> The second compound contains at least one deuterium. <Condition 15> The second compound contains at least one tert-butyl group.
[0143] Specific examples of the second compound According to one embodiment, the second compound is selected from the following Compounds E1 to E47 (Chemical Formulas 21 to 23) and deuterium-containing derivatives thereof.
[0144] [Chemical]
[0145] [Chemical]
[0146] [Chemical]
[0147] Explanation regarding Chemical Formula 3 In this specification, the organometallic compound contained in the light-emitting layer is an organometallic compound represented by the following Chemical Formula 3 (Chemical Formula 24).
[0148] [Chemical]
[0149] In the above Chemical Formula 3, M 31 is a transition metal, X 11 ~X 14 are, independently of each other, C or N, X 11 and M 31 of the bond between, X 12 and M 31 of the bond between, X 13 and M 31 of the bond between, and X 14 and M 31 of the bond between, two of them are coordination bonds and the remaining two are covalent bonds, Ring CY 31 ~Ring CY 34 are, independently of each other, a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group, T 31 is a single bond, a double bond, *-N(R 35a )-*’, *-B(R 35a )-*’, *-P(R 35a )-*’, *-C(R35a )(R 35b )-*’、*-Si(R 35a )(R 35b )-*’、*-Ge(R 35a )(R 35b )-*’、*-S-*’、*-Se-*’、*-O-*’、*-C(=O)-*’、*-S(=O)-*’、*-S(=O)2-*’、*-C(R 35a )=*’、*=C(R 35a )-*’、*-C(R 35a )=C(R 35b )-*’、*-C(=S)-*’、*-C≡C-*’、 at least one R 10a substituted or unsubstituted C5-C 30 carbocyclic group, or at least one R 10a substituted or unsubstituted C1-C 30 heterocyclic group, and T 32 is a single bond, double bond, *-N(R 36a )-*’、*-B(R 36a )-*’、*-P(R 36a )-*’、*-C(R 36a )(R 36b )-*’、*-Si(R 36a )(R 36b )-*’、*-Ge(R 36a )(R 36b )-*’、*-S-*’、*-Se-*’、*-O-*’、*-C(=O)-*’、*-S(=O)-*’、*-S(=O)2-*’、*-C(R 36a )=*’、*=C(R 36a )-*’、*-C(R 36a )=C(R 36b )-*’、*-C(=S)-*’、*-C≡C-*’、 at least one R 10a substituted or unsubstituted C5-C 30 carbocyclic group, or at least one R 10a substituted or unsubstituted C1-C 30 heterocyclic group, and T 33 is a single bond, double bond, *-N(R 37a )-*’、*-B(R 37a )-*’、*-P(R 37a)-*’, *-C(R 37a )(R 37b )-*’, *-Si(R 37a )(R 37b )-*’, *-Ge(R 37a )(R 37b )-*’, *-S-*’, *-Se-*’, *-O-*’, *-C(=O)-*’, *-S(=O)-*’, *-S(=O)2-*’, *-C(R 37a )=*’, *=C(R 37a )-*’, *-C(R 37a )=C(R 37b )-*’, *-C(=S)-*’, *-C≡C-*’, at least one R 10a substituted or unsubstituted C5-C 30 carbocyclic group, or at least one R 10a substituted or unsubstituted C1-C 30 heterocyclic group, and T 34 is a single bond, double bond, *-N(R 38a )(R 38a )-*, *-B(R 38a )(R 38a )-*, *-P(R 38b )(R 38a )-*, *-Si(R 38b )(R 38a )-*, *-Ge(R 38b )(R 38a )-*, *=C(R 38a )-*, *-C(R 38a )=C(R 38b )-*, *-C(=S)-*, *-C≡C-*, at least one R 10a substituted or unsubstituted C5-C 30 carbocyclic group, or at least one R 10a substituted or unsubstituted C1-C 30 heterocyclic group, and n31 to n34 are, independently of each other, integers from 0 to 5, provided that 3 or more of n31 to n34 are, independently of each other, integers from 1 to 5, and When n31 is 0, T 31 does not exist. When n32 is 0, T 32 does not exist. When n33 is 0, T 33 does not exist. When n34 is 0, T 34 does not exist. When n31 is 2 or more, two or more Ts 31 may be the same as or different from each other. When n32 is 2 or more, two or more Ts 32 may be the same as or different from each other. When n33 is 2 or more, two or more Ts 33 may be the same as or different from each other. When n34 is 2 or more, two or more Ts 34 may be the same as or different from each other. R 31 ~R 34 、R 35a 、R 35b 、R 36a 、R 36b 、R 37a 、R 37b 、R 38a and R 38b are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, -SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C7-C60 an arylalkyl group, a substituted or unsubstituted C6-C 60 an aryloxy group, a substituted or unsubstituted C6-C 60 an arylthio group, a substituted or unsubstituted C1-C 60 a heteroaryl group, a substituted or unsubstituted C2-C 60 a heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), and a31 to a34 are, independently of one another, integers from 0 to 20, and two or more of the a31 Rs 31 are optionally bonded to each other, and at least one R 10a substituted or unsubstituted C5-C 30 carbocyclic group, or at least one R 10a substituted or unsubstituted C1-C 30 heterocyclic group can be formed, two or more of the a32 Rs 32 are optionally bonded to each other, and at least one R 10a substituted or unsubstituted C5-C 30 carbocyclic group, or at least one R 10a substituted or unsubstituted C1-C 30 heterocyclic group can be formed, two or more of the a33 Rs 33 are optionally bonded to each other, and at least one R 10a substituted or unsubstituted C5-C 30 carbocyclic group, or at least one R 10a substituted or unsubstituted C1-C 30 heterocyclic group can be formed, two or more of the a34 Rs 34 are optionally bonded to each other, and at least one R 10a substituted or unsubstituted C5-C 30 carbocyclic group, or at least one R 10asubstituted or unsubstituted C1-C 30 can form a heterocyclic group, R 31 , R 32 , R 33 , R 34 , R 35a , R 35b , R 36a , R 36b , R 37a , R 37b , R 38a and R 38b among which two or more are selectively bonded to each other, and at least one R 10a substituted or unsubstituted C5-C 30 carbocyclic group, or at least one R 10a substituted or unsubstituted C1-C 30 can form a heterocyclic group, The description of the aforementioned R 10a refers to the description of the aforementioned R 31 , * and *’ are respectively the bonding sites with adjacent atoms, The aforementioned substituted C1-C 60 alkyl group, substituted C2-C 60 alkenyl group, substituted C2-C 60 alkynyl group, substituted C1-C 60 alkoxy group, substituted C3-C 10 cycloalkyl group, substituted C1-C 10 heterocycloalkyl group, substituted C3-C 10 cycloalkenyl group, substituted C1-C 10 heterocycloalkenyl group, substituted C6-C 60 aryl group, substituted C7-C 60 arylalkyl group, substituted C6-C 60 aryloxy group, substituted C6-C 60 arylthio group, substituted C1-C 60 heteroaryl group, substituted C2-C 60 The substituents of the heteroarylalkyl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic hetero-condensed polycyclic group are, Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, or C1-C 60 alkoxy group; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic hetero-fused polycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 13 )(Q 14 )(Q 15 ), -Ge(Q 13 )(Q 14 )(Q 15 ), -B(Q 16 )(Q 17 ), -P(=O)(Q 18 )(Q 19 ), -P(Q 18 )(Q 19 ), or an alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C2-C 60 alkynyl group, or C1-C 60 alkoxy group; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero-condensed polycyclic group, -N(Q 21 )(Q 22 ), -Si(Q 23 )(Q 24 )(Q 25 ), -Ge(Q 23 )(Q 24 )(Q 25 ), -B(Q 26 )(Q 27 ), -P(=O)(Q 28 )(Q 29 ), -P(Q 28 )(Q 29 ), or a C3-C substituted or unsubstituted with any combination thereof 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic hetero-condensed polycyclic group; -N(Q31 )(Q 32 )、 -Si(Q 33 )(Q 34 )(Q 35 )、 -Ge(Q 33 )(Q 34 )(Q 35 )、 -B(Q 36 )(Q 37 )、 -P(=O)(Q 38 )(Q 39 )、 or -P(Q 38 )(Q 39 ); or any combination thereof; and the aforementioned Q1 - Q9, Q 11 ~Q 19 、 Q 21 ~Q 29 、 and Q 31 ~Q 39 are, independently of each other, hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; amidino group; hydrazine group; hydrazone group; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphoric acid group or its salt; deuterium, C1 - C 60 alkyl group, C6 - C 60 aryl group, or a C1 - C 60 alkyl group which is substituted or unsubstituted with any combination thereof; C2 - C 60 alkenyl group; C2 - C 60 alkynyl group; C1 - C 60 alkoxy group; C3 - C 10 cycloalkyl group; C1 - C 10 heterocycloalkyl group; C3 - C 10 cycloalkenyl group; C1 - C 10 heterocycloalkenyl group; deuterium, C1 - C 60 alkyl group, C6 - C 60 aryl group, or a C6 - C 60 aryl group which is substituted or unsubstituted with any combination thereof; C6 - C 60 aryloxy group; C6 - C 60 arylthio group; C1 - C 60 heteroaryl group; monovalent non - aromatic condensed polycyclic group; or monovalent non - aromatic hetero - condensed polycyclic group; and
[0150] According to one embodiment, in the chemical formula 3, M 31 is Pt, Pd, or Au.
[0151] According to another embodiment, in the chemical formula 3, M 31 is Pt or Pd.
[0152] According to still another embodiment, in the chemical formula 3, the bond between X 11 and M 31 is a coordination bond.
[0153] According to still another embodiment, in the chemical formula 3, X 11 is C, and the bond between X 11 and M 31 is a coordination bond. That is, in the chemical formula 3, X 11 is C in the carbene moiety.
[0154] According to still another embodiment, in the chemical formula 3, ring CY 31 ~ ring CY 34 are, independently of each other, i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, or v) a condensed ring in which one or more first rings and one or more second rings are condensed with each other, the first ring is a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, or a triazasilole group, The second ring is an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, an oxazine group, a thiazine group, a dihydropyrazine group, a dihydropyridine group, or a dihydroazasilane group.
[0155] According to still another embodiment, in Chemical Formula 3, ring CY 31 is an imidazole group, a benzimidazole group, a naphthimidazole group, or a pyridoimidazole group.
[0156] According to still another embodiment, in Chemical Formula 3, ring CY 32 and CY 34 are, independently of each other, a benzene group, a naphthalene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a quinoline group, an isoquinoline group, a benzene group condensed with an adamantane group, or a benzene group condensed with a norbornane group.
[0157] According to still another embodiment, in Chemical Formula 3, ring CY 33 is a benzene group, a naphthalene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a benzene group condensed with an adamantane group, a benzene group condensed with a norbornane group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a benzocarbazole group, a naphthocarbazole group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azabenzocarbazole group, or an azanaphthocarbazole group.
[0158] According to still another embodiment, in Chemical Formula 3, T 31 is *-S-*’ or *-O-*’.
[0159] According to still another embodiment, in Chemical Formula 3, T 32 and T 33 are each a single bond.
[0160] According to still other embodiments, in the chemical formula 3, X 11 , X 12 and X 13 are C, and X 14 is N.
[0161] According to one embodiment, R 31 ~R 34 , R 35a , R 35b , R 36a , R 36b , R 37a , R 37b , R 38a and R 38b are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano group (CN), nitro group, amino group, C1-C 20 alkyl group, or C1-C 20 alkoxy group; a C1-C 20 alkyl group or a C1-C 20 alkoxy group substituted with at least one of deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano group (CN), nitro group, amino group, and phenyl group; or a cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, or anthracenyl group, which is substituted or unsubstituted with at least one of deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano group (CN), nitro group, amino group, C1-C 20 alkyl group, C1-C 20 alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, or anthracenyl group; is.
[0162] According to one embodiment, the organometallic compound represented by the chemical formula 3 is an organometallic compound represented by the following chemical formula 3-1 (Chemical Formula 25) or an organometallic compound represented by the following chemical formula 3-2 (Chemical Formula 26):
[0163]
Chemical Formula
[0164]
Chemical Formula
[0165] In the chemical formula 3-1, the bond between the carbon of the imidazole group and M 31 is a coordination bond. That is, in the chemical formula 3-1, the imidazole group contains a carbene moiety bonded to M 31 .
[0166] In the chemical formula 3-2, the bond between the carbon of the benzimidazole group and M 31 is a coordination bond. That is, in the chemical formula 3-2, the benzimidazole group contains a carbene moiety bonded to M 31 .
[0167] Therefore, it is easily understood that the following chemical formula 3-1’ (Chemical Formula 27), in which the carbon bonded to M 31 in the imidazole group is represented as carbene, is identical to the chemical formula 3-1, and the following chemical formula 3-2’ (Chemical Formula 28), in which the carbon bonded to M 31 in the benzimidazole group is represented as carbene, is identical to the chemical formula 3-2.
[0168]
Chemical Formula
[0169]
Chemical Formula
[0170] In the above chemical formulas 3-1 and 3-2, M 31 , CY 32 , CY 33 , CY 34 , X 12 , X 13 , X 14 , T 31 , T 32 , T 33 , n31, n32, n33, R 32 , R 33 , R 34 , the descriptions related to a32, a33, a34 respectively refer to what is described in this specification, R 311 ~R 317 Each refers to the description related to R 31 in this specification.
[0171] According to one embodiment, in the above chemical formulas 3-1 and 3-2, R 311 ~R 317 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, -SF5, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, or phosphoric acid group or its salt; deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, -SF5, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, or an optionally substituted or unsubstituted C1-C 20 alkyl group or C1-C 20 alkoxy group; deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, -SF5, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1-C 20 alkyl group, C1-C 20A C3-C optionally substituted with an alkoxy group or any combination thereof, or 10 a cycloalkyl group, a C1-C 10 heterocycloalkyl group, a C6-C 60 aryl group, a C7-C 60 arylalkyl group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, a C1-C 60 heteroaryl group, an optionally substituted C2-C 60 heteroarylalkyl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group; or -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9); wherein.
[0172] For example, in the above Chemical Formulas 3-1 and 3-2, R 311 ~R 317 at least one of which is a C1-C optionally substituted with at least one of a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a phenyl group, a cumyl group, or a combination thereof, 20 an alkyl group, a C6-C 60 an aryl group, or a C7-C 60 arylalkyl group.
[0173] According to one embodiment, the organometallic compound represented by the above Chemical Formula 3 is an organometallic compound represented by the following Chemical Formula 3-1(1) (Chemical Formula 29), or an organometallic compound represented by the following Chemical Formula 3-2(1) (Chemical Formula 30).
[0174]
Chemical Formula
[0175]
Chemical Formula
[0176] In the chemical formulas 3-1(1) and 3-2(1), M 31 , X 12 , X 13 , X 14 and T 31 For the explanations related to each, refer to what is described in this specification. R 311 ~R 317 For the explanations related to each, refer to the explanation of R 31 in this specification. R 321 ~R 323 For the explanations related to each, refer to the explanation of R 32 in this specification. R 321 ~R 323 Among them, two or more can be selectively bonded to each other to form a C5-C 10a carbocyclic group which is substituted or unsubstituted with at least one R 30 , or a C1-C 10a heterocyclic group which is substituted or unsubstituted with at least one R 30 . R 331 ~R 336 For the explanations related to each, refer to the explanation of R 33 in this specification. 331 ~R 336 Among them, two or more can be selectively bonded to each other to form a C5-C 10a carbocyclic group which is substituted or unsubstituted with at least one R 30 , or a C1-C 10a heterocyclic group which is substituted or unsubstituted with at least one R 30 . R 341 ~R 344 For the explanations related to each, refer to the explanation of R 34 in this specification. 341 ~R 344 Among them, two or more can be selectively bonded to each other to form a C5-C 10a carbocyclic group which is substituted or unsubstituted with at least one R 30 and at least one R10a is a C1-C which may be substituted or unsubstituted 30 and can form a heterocyclic group.
[0177] Explanation regarding Chemical Formula 5 In the present specification, the organometallic compound contained in the light-emitting layer is an organometallic compound represented by the following Chemical Formula 5 (Formula 31).
[0178] [Chemical Formula]
[0179] In the Chemical Formula 5, M 51 is a transition metal.
[0180] For example, the M 51 is a first transition metal, a second transition metal, or a third transition metal.
[0181] As yet another example, the M 51 is iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).
[0182] According to one embodiment, the M 51 is Ir, Pt, Os, or Rh.
[0183] According to another embodiment, the M 51 is Ir or Os.
[0184] In the Chemical Formula 5, L 51 is a ligand represented by the following Chemical Formula 5A (Formula 32), and L 52 is a ligand represented by the following Chemical Formula 5B (Formula 33).
[0185] [Chemical Formula]
[0186]
Chem.
[0187] For the descriptions related to Chemical Formulas 5A and 5B, refer to the places described in this specification respectively.
[0188] In the Chemical Formula 5, n51 is 1, 2 or 3; when n51 is 2 or more, two or more Ls 51 may be the same as or different from each other.
[0189] In the Chemical Formula 5, n52 is 0, 1 or 2; when n52 is 2, two Ls 52 may be the same as or different from each other.
[0190] In the Chemical Formula 5, the sum of n51 and n52 is 2 or 3. For example, the sum of n51 and n52 is 3.
[0191] According to one embodiment, in the Chemical Formula 5, i) M is Ir and n51 + n52 is 3, or ii) M is Pt and n51 + n52 is 2.
[0192] According to other embodiments, in the Chemical Formula 5, M is Ir, and i) n51 is 1 and n52 is 2, or ii) n51 is 2 and n52 is 1.
[0193] In the Chemical Formula 5, L 51 and L 52 are different from each other.
[0194] In the Chemical Formulas 5A and 5B, Y 51 ~Y 54 are, independently of each other, C or N. For example, each of the Ys 51 and Y 53 is N, and each of the Ys 52 and Y 54 is C.
[0195] In the above chemical formulas 5A and 5B, ring CY 51 ~ ring CY 54 are, independently of each other, C5-C 30 carbocyclic group or C1-C 30 heterocyclic group.
[0196] For example, in chemical formulas 5A and 5B, the above ring CY 51 ~ ring CY 54 are, independently of each other, i) a third ring, ii) a fourth ring, iii) a condensed ring in which two or more third rings are condensed with each other, iv) a condensed ring in which two or more fourth rings are condensed with each other, or v) a condensed ring in which one or more third rings and one or more fourth rings are condensed with each other, The third ring is a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an azasilole group, The fourth ring is an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
[0197] As still another example, in the chemical formulas 5A and 5B, the ring CY1 to ring CY4 are, independently of each other, a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, a pyrrole group, a furan group, a thiophene group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzogermole group, a benzoselenophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzogermole group, a dibenzoselenophene group, a benzofluorene group, a benzocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a naphthobenzosilole group, a naphthobenzoborole group, a naphthobenzophosphole group, a naphthobenzogermole group, a naphthobenzoselenophene group, a dibenzofluorene group, a dibenzocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, a dinaphthosilole group, a dinaphthoborole group, a dinaphthophosphole group, a dinaphthogermole group, a dinaphthoselenophene group, an indenophenanthrene group, an indophenanthrene group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a phenanthrobenzosilole group, a phenanthrobenzoborole group, a phenanthrobenzophosphole group, a phenanthrobenzogermole group, a phenanthrobenzoselenophene group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, azaindene group, azaindole group, azabenzofuran group, azabenzothiophene group, azabenzosilole group, azabenzoborole group, azabenzophosphole group, azabenzogermole group, azabenzoselenophene group, azafluorene group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzosilole group, azadibenzoborole group, azadibenzophosphole group, azadibenzogermole group, azadibenzoselenophene group, azabenzofluoren group, azabenzocarbazole group, azanaphthobenzofuran group, azanaphthobenzothiophene group, azanaphthobenzosilole group, azanaphthobenzoborole group, azanaphthobenzophosphole group, azanaphthobenzogermole group, azanaphthobenzoselenophene group, azadibenzofluoren group, azadibenzocarbazole group, azadinafuran group, azadinathiophene group, azadinasilole group, azadinaborole group, azadinaophosphole group, azadinaogermole group, azadinaselenophene group, azaindenophenanthrene group, azaindrophenanthrene group, azaphenanthrobenzofuran group, azaphenanthrobenzothiophene group, azaphenanthrobenzosilole group, azaphenanthrobenzoborole group, azaphenanthrobenzophosphole group, azaphenanthrobenzogermole group, azaphenanthrobenzoselenophene group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, benzoquinoline group, benzoisoquinoline group, benzoxquinoline group, benzquinazoline group, phenanthroline group, phenanthridine group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, azasilole group, azaborole group, azaphosphole group, azagermole group, azaselenophene group, benzopyrrole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, benzoxadiazole group, benzothiadiazole group, pyridinopyrrole group, pyridinopyrazole group, pyridinoimidazole group, pyridinooxazole group, pyridinoisoxazole group, pyridinothiazole group, pyridinoisothiazole group, pyridinooxadiazole group, pyridinothiadiazole group, pyrimidinopyrrole group, pyrimidinopyrazole group, pyrimidineimidazole group, pyrimidineoxazole group, pyrimidineisoxazole group, pyrimidinothiazole group, pyrimidinoisothiazole group, pyrimidineoxadiazole group, pyrimidinothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, adamantane group, norbornane group, norbornene group, benzene group condensed with cyclohexane group, benzene group condensed with norbornane group, pyridine group condensed with cyclohexane group, or pyridine group condensed with norbornane group.,
[0198] For example, in the chemical formulas 5A and 5B, ring CY 51 and ring CY 53 are different from each other.,
[0199] As another example, in the chemical formulas 5A and 5B, ring CY 52 and ring CY 54 are different from each other.,
[0200] As still another example, in the chemical formulas 5A and 5B, ring CY 51 ~ring CY 54 are each different from one another.
[0201] In the chemical formulas 5A and 5B, R 51 ~R 54 are, independently of one another, hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C1-C 60 alkylthio group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group, -N(Q 51 )(Q 52 )、-Si(Q 53 )(Q 54 )(Q 55 )、-Ge(Q 53 )(Q 54 )(Q 55 )、-B(Q 56 )(Q 57 )、-P(=O)(Q 58 )(Q 59) or -P(Q 58 )(Q 59 ) is. Regarding the description of the above Q 51 ~Q 59 , refer to the places described in this specification respectively.
[0202] According to one embodiment, in the chemical formulas 5A and 5B, R 51 ~R 54 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SF5, C1-C 20 alkyl group, C1-C 20 alkoxy group, or C1-C 20 alkylthio group; deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10 alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, (C1-C 20 alkyl)cyclopentyl group, (C1-C 20 alkyl)cyclohexyl group, (C1-C 20 alkyl)cycloheptyl group, (C1-C 20 alkyl)cyclooctyl group, (C1-C 20 alkyl)adamantanyl group, (C1-C 20 alkyl)norbornanyl group, (C1-C 20 alkyl)norbornenyl group, (C1-C 20 alkyl)cyclopentenyl group, (C1-C 20(Alkyl)cyclohexenyl group, (C1-C 20 (Alkyl)cycloheptenyl group, (C1-C 20 (Alkyl)bicyclo[1.1.1]pentyl group, (C1-C 20 (Alkyl)bicyclo[2.1.1]hexyl group, (C1-C 20 (Alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20 (Alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, or a C1-C substituted with any combination thereof 20 Alkyl group, C1-C 20 Alkoxy group, or C1-C 20 Alkylthio group; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 (Phenyl)C1-C alkyl group 10 Alkyl group, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, (C1-C 20 (Alkyl)cyclopentyl group, (C1-C 20 (Alkyl)cyclohexyl group, (C1-C 20 (Alkyl)cycloheptyl group, (C1-C 20 (Alkyl)cyclooctyl group, (C1-C 20 (Alkyl)adamantanyl group, (C1-C 20 (Alkyl)norbornanyl group, (C1-C 20 (Alkyl)norbornenyl group, (C1-C 20 (Alkyl)cyclopentenyl group, (C1-C 20 (Alkyl)cyclohexenyl group, (C1-C20 (C1-C alkyl)cycloheptenyl group 20 (C1-C alkyl)bicyclo[1.1.1]pentyl group 20 (C1-C alkyl)bicyclo[2.1.1]hexyl group 20 (C1-C alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20 (C1-C alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzoisothiazolyl group, benzoxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, or a substituted or unsubstituted cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20(alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzoisothiazolyl group, benzoxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group, or azadibenzothiophenyl group; or -N(Q 51 )(Q 52 )、-Ge(Q 53 )(Q 54 )(Q 55 )、-B(Q 56 )(Q 57 )、-P(=O)(Q 58 )(Q 59 )、or -P(Q 58 )(Q 59 ); where Q 51 ~Q 59 are, independently of each other, -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or deuterium, C1-C 10An n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, phenyl group, biphenyl group, or naphthyl group, which is substituted or unsubstituted with an alkyl group, phenyl group, or any combination thereof;
[0203] According to another embodiment, said R 51 ~R 54 are, independently of one another, hydrogen, deuterium, -F, or a cyano group; deuterium, cyano group, C3-C 10 cycloalkyl group, deuterated C3-C 10 cycloalkyl group, fluorinated C3-C 10 cycloalkyl group, (C1-C 20 alkyl)C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, deuterated C1-C 10 heterocycloalkyl group, fluorinated C1-C 10 heterocycloalkyl group, (C1-C 20 alkyl)C1-C 10 heterocycloalkyl group, phenyl group, deuterated phenyl group, fluorinated phenyl group, (C1-C 20 alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C1-C 20 alkyl)biphenyl group, dibenzofuranyl group, deuterated dibenzofuranyl group, fluorinated dibenzofuranyl group, (C1-C 20 alkyl)dibenzofuranyl group, dibenzothiophenyl group, deuterated dibenzothiophenyl group, fluorinated dibenzothiophenyl group, (C1-C 20 alkyl)dibenzothiophenyl group, or a C1-C 20 alkyl group which is substituted or unsubstituted with any combination thereof; deuterium, cyano group, C1-C 20 alkyl group, deuterated C1-C 20 alkyl group, fluorinated C1-C20 an alkyl group, C1-C 20 an alkoxy group, deuterated C1-C 20 an alkoxy group, fluorinated C1-C 20 an alkoxy group, C3-C 10 a cycloalkyl group, deuterated C3-C 10 a cycloalkyl group, fluorinated C3-C 10 a cycloalkyl group, (C1-C 20 alkyl)C3-C 10 a cycloalkyl group, C1-C 10 a heterocycloalkyl group, deuterated C1-C 10 a heterocycloalkyl group, fluorinated C1-C 10 a heterocycloalkyl group, (C1-C 20 alkyl)C1-C 10 a heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, (C1-C 20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, (C1-C 20 alkyl)biphenyl group, a dibenzofuranyl group, a deuterated dibenzofuranyl group, a fluorinated dibenzofuranyl group, (C1-C 20 alkyl)dibenzofuranyl group, a dibenzothiophenyl group, a deuterated dibenzothiophenyl group, a fluorinated dibenzothiophenyl group, (C1-C 20 alkyl)dibenzothiophenyl group, or a C3-C substituted or unsubstituted with any combination thereof 10 a cycloalkyl group, C1-C 10 a heterocycloalkyl group, a phenyl group, or a biphenyl group; or -Si(Q 53 )(Q 54 )(Q 55 ) or -Ge(Q 53 )(Q 54 )(Q 55 ); where
[0204] In the above chemical formulas 5A and 5B, each of b51 to b54 is R 51 ~R 54indicates the number, and independently of each other, they are integers from 0 to 20. When b51 is 2 or more, two or more Rs 51 may be the same as or different from each other. When b52 is 2 or more, two or more Rs 52 may be the same as or different from each other. When b53 is 2 or more, two or more Rs 53 may be the same as or different from each other. When b54 is 2 or more, two or more Rs 54 may be the same as or different from each other. For example, b51 to b54 are independently integers from 0 to 8.
[0205] According to one embodiment, in Chemical Formula 5A, Y 52 is C, and the bond between Y 52 and M 51 is a covalent bond, and at least one of the b52 Rs 52 is a cyano group or -F.
[0206] According to another embodiment, in Chemical Formula 5A, Y 51 is N, and the bond between Y 51 and M 51 is a coordination bond, CY 51 is an imidazole group, a triazole group, a benzimidazole group, or a triazolopyridine group, and at least one of the b52 Rs 52 is a cyano group or -F.
[0207] According to still another embodiment, in Chemical Formula 5A, Y 51 is C, and the bond between Y 51 and M 51 is a coordination bond.
[0208] According to still another embodiment, in Chemical Formula 5A, Y 51 is C, and the bond between Y 51 and M 51 is a coordination bond, CY 51 is a benzimidazole group or an imidazopyrazine group.
[0209] Specific examples of the organometallic compound According to one embodiment, the organometallic compound (for example, the organometallic compound represented by the chemical formula 3 and the organometallic compound represented by the chemical formula 5) contained in the light-emitting layer is one of the following compounds P1 to P52 (Chemical Formulas 34 to 35).
[0210]
Chemical Formula
[0211]
Chemical Formula
[0212] Explanation regarding Chemical Formula 4 In this specification, the thermally activated delayed fluorescence substance contained in the light-emitting layer is a polycyclic compound represented by the following chemical formula 4 (Chemical Formula 36).
[0213]
Chemical Formula
[0214] In the chemical formula 4, Z is B or N, ring CY 41 ~CY 43 are, independently of each other, a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group, Y 41 is a single bond, *-N(R 44 )-*’, *-B(R 44 )-*’, *-P(R 44 )-*’, *-C(R 44 )(R 45 )-*’, *-Si(R 44 )(R 45 )-*’, *-Ge(R 44 )(R 45 )-*’, *-O-*’, *-S-*’, *-Se-*’, *-C(=O)-*’, or *-S(=O)2-*’, Y 42 is a single bond, *-N(R 46 )-*, *-B(R 46 )-*, *-P(R 46 )-*, *-C(R 46 )(R 47 )-*, *-Si(R 46 )(R 47 )-*, *-Ge(R 46 )(R 47 )-*, *-O-*, *-S-*, *-Se-*, *-C(=O)-*, or *-S(=O)2-*, and Y 43 is a single bond, *-N(R 48 )-*, *-B(R 48 )-*, *-P(R 48 )-*, *-C(R 48 )(R 49 )-*, *-Si(R 48 )(R 49 )-*, *-Ge(R 48 )(R 49 )-*, *-O-*, *-S-*, *-Se-*, *-C(=O)-*, or *-S(=O)2-*, and b41 to b43 are, independently of one another, 0 or 1, when b41 is 0, Y 41 does not exist, when b42 is 0, Y 42 does not exist, and when b43 is 0, Y 43 does not exist, R 41 ~R 49 are, independently of one another, hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C3-C 10A cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C7-C 60 arylalkyl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted C2-C 60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), and a41 to a43 are, independently of each other, integers from 0 to 20, Among a41 R 41 Two or more of them are selectively bonded to each other, and at least one R 10b substituted or unsubstituted C5-C 30 carbocyclic group, or at least one R 10b substituted or unsubstituted C1-C 30 heterocyclic group can be formed, Among a42 R 42 Two or more of them are selectively bonded to each other, and at least one R 10b substituted or unsubstituted C5-C 30 carbocyclic group, or at least one R 10b substituted or unsubstituted C1-C 30 heterocyclic group can be formed, Among a43 R 43 Two or more of them are selectively bonded to each other, and at least one R 10b substituted or unsubstituted C5-C 30 carbocyclic group, or at least one R 10bsubstituted or unsubstituted C1-C 30 can form a heterocyclic group, R 41 ~R 49 two or more of which are selectively bonded to each other, and at least one R 10b substituted or unsubstituted C5-C 30 carbocyclic group, or at least one R 10b substituted or unsubstituted C1-C 30 can form a heterocyclic group, the description of the aforementioned R 10b refers to the description of the aforementioned R 41 and refer to it, * and *’ are respectively the bonding sites with adjacent atoms, the aforementioned substituted C1-C 60 alkyl group, substituted C2-C 60 alkenyl group, substituted C2-C 60 alkynyl group, substituted C1-C 60 alkoxy group, substituted C3-C 10 cycloalkyl group, substituted C1-C 10 heterocycloalkyl group, substituted C3-C 10 cycloalkenyl group, substituted C1-C 10 heterocycloalkenyl group, substituted C6-C 60 aryl group, substituted C7-C 60 arylalkyl group, substituted C6-C 60 aryloxy group, substituted C6-C 60 arylthio group, substituted C1-C 60 heteroaryl group, substituted C2-C 60 the substituents of heteroarylalkyl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic hetero-condensed polycyclic group are, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 60 alkyl group, C2-C60 an alkenyl group, C2-C 60 an alkynyl group, or C1-C 60 an alkoxy group; deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, C3-C 10 a cycloalkyl group, C1-C 10 a heterocycloalkyl group, C3-C 10 a cycloalkenyl group, C1-C 10 a heterocycloalkenyl group, C6-C 60 an aryl group, C6-C 60 an aryloxy group, C6-C 60 an arylthio group, C1-C 60 a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic hetero-condensed polycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-Ge(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19 )、-P(Q 18 )(Q 19 )、or a C1-C alkyl group, a C2-C alkenyl group, a C2-C alkynyl group, or a C1-C alkoxy group substituted with any combination thereof; 60 an alkenyl group, C2-C 60 an alkynyl group, C2-C 60 an alkynyl group, or C1-C 60 an alkoxy group; deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, C1-C 60 an alkyl group, C2-C 60Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic hetero-fused polycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-Ge(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28 )(Q 29 )、-P(Q 28 )(Q 29 )、or a C3-C substituted or unsubstituted with any combination thereof 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic hetero-fused polycyclic group; -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-Ge(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37)、 -P(=O)(Q 38 )(Q 39 )、 or -P(Q 38 )(Q 39 ); or, any combination thereof; and the aforementioned Q1 to Q9, Q 11 ~Q 19 、 Q 21 ~Q 29 and Q 31 ~Q 39 are, independently of each other, hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; amidino group; hydrazine group; hydrazone group; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphoric acid group or its salt; deuterium, C1-C 60 alkyl group, C6-C 60 aryl group, or a C1-C 60 alkyl group which is substituted or unsubstituted with any combination thereof; C2-C 60 alkenyl group; C2-C 60 alkynyl group; C1-C 60 alkoxy group; C3-C 10 cycloalkyl group; C1-C 10 heterocycloalkyl group; C3-C 10 cycloalkenyl group; C1-C 10 heterocycloalkenyl group; deuterium, C1-C 60 alkyl group, C6-C 60 aryl group, or a C6-C 60 aryl group which is substituted or unsubstituted with any combination thereof; C6-C 60 aryloxy group; C6-C 60 arylthio group; C1-C 60 heteroaryl group; monovalent non-aromatic condensed polycyclic group; or monovalent non-aromatic hetero-condensed polycyclic group; and
[0215] According to one embodiment, the ring CY 41 ~CY 43 are, independently of each other, i) benzene group, or ii) a polycyclic group in which two or more C3-C 60 cyclic groups are condensed with each other. Among the polycyclic groups, two C3-C 60The cyclic groups are condensed with each other while sharing boron (B) or nitrogen (N).
[0216] According to other embodiments, at least one of b41 to b43, or at least two of b41 to b43 are each 1. As yet another example, two of b41 to b43 are 1 and the remaining one is 0.
[0217] According to still other embodiments, R 41 ~R 49 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group (CN), a nitro group, an amino group, a C1-C 60 alkyl group, or a C1-C 60 alkoxy group; deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group (CN), a nitro group, an amino group, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenyl group, and a C1-C 60 alkyl group or a C1-C 60 alkoxy group substituted with at least one of; or deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group (CN), a nitro group, an amino group, a C1-C 60 alkyl group, a C1-C 60A cycloalkyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, or a carbazolyl group, which is substituted or unsubstituted with at least one of an alkoxy group, cycloalkyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, or a carbazolyl group; is provided.
[0218] According to still other embodiments, the polycyclic compound represented by Chemical Formula 4 is a polycyclic compound represented by one of the following Chemical Formulas 4-1 to 4-9 (Chemical Formulas 37 to 45):
[0219]
Chem.
[0220]
Chem.
[0221]
Chem.
[0222]
Chem.
[0223]
Chem.
[0224]
Chem.
[0225]
Chem.
[0226]
Chem.
[0227]
Chem.
[0228] In Chemical Formulas 4-1 to 4-9, Each of Z1 to Z3 refers to the description of Z in this specification. Y 41 and Y 42 refers to the description in this specification. Y 44 ~Y 47 each refers to Y in this specification 41 and Y 42 and refers to the description related thereto. R 411 refers to R in this specification 41 and refers to the description related to R. R 421 refers to R in this specification 42 and refers to the description related to R. R 431 and R 432 each refers to R in this specification 43 and refers to the description related to R. R 441 refers to R in this specification 41 and refers to the description related to R. R 451 refers to R in this specification 42 and refers to the description related to R. R 461 refers to R in this specification 43 and refers to the description related thereto. a411 is an integer selected from 0 to 4, a421 is an integer selected from 0 to 3, a431 is an integer selected from 0 to 4, a441 is an integer selected from 0 to 4, a451 is an integer selected from 0 to 3, a461 is an integer selected from 0 to 3.
[0229] Specific examples of the thermally activated delayed fluorescence substance According to one embodiment, the thermally activated delayed fluorescence substance (for example, the polycyclic compound represented by the chemical formula 4) is selected from the following compounds D1 to D30 (Chemical Formula 46 to Chemical Formula 48).
[0230]
Chemical Formula
[0231]
Chemical Formula
[0232]
Chem.
[0233] Explanation regarding Figure 1 FIG. 1 schematically shows a cross-sectional view of one organic light-emitting element 10 among the light-emitting elements according to an embodiment of the present invention. Hereinafter, with reference to FIG. 1, the structure and manufacturing method of the organic light-emitting element according to an embodiment of the present invention will be described as follows.
[0234] The organic light-emitting element 10 in FIG. 1 includes a first electrode 11, a second electrode 19 facing the first electrode 11, and an intermediate layer 10A disposed between the first electrode 11 and the second electrode 19.
[0235] The intermediate layer 10A includes a light-emitting layer 15, a hole transport region 12 is disposed between the first electrode 11 and the light-emitting layer 15, and an electron transport region 17 is disposed between the light-emitting layer 15 and the second electrode 19. The hole transport region 12 further includes a first layer (not shown). The first layer can be in direct contact with the light-emitting layer 15.
[0236] A substrate may be further disposed below the first electrode 11 or above the second electrode 19. As the substrate, a substrate used in a normal organic light-emitting element can be used, but a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness can be used.
[0237] [First Electrode 11] The first electrode 11 is formed, for example, by providing a first electrode material on the upper part of the substrate using a vapor deposition method or a sputtering method or the like. The first electrode 11 is an anode. The first electrode material includes a material having a high work function so that hole injection is easy.
[0238] The first electrode 11 is a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. To form the first electrode 11 that is a transmissive electrode, the material for the first electrode includes indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. Alternatively, to form the first electrode 11 that is a semi-transmissive electrode or a reflective electrode, the material for the first electrode includes magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
[0239] The first electrode 11 can have a single layer or a multilayer structure including two or more layers.
[0240] [Light-emitting layer 15] The thickness of the light-emitting layer 15 is about 100 Å to about 1000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light-emitting layer 15 satisfies the above range, excellent light-emitting characteristics can be exhibited without a substantial increase in the driving voltage.
[0241] According to one embodiment, the light-emitting layer 15 includes a first compound and an organometallic compound as described herein. Further, in addition to the first compound and the organometallic compound, the light-emitting layer 15 may further include at least one of a second compound and a thermally activated delayed fluorescence material.
[0242] [Hole transport region 12] In the organic light-emitting device 10, a hole transport region 12 is disposed between the first electrode 11 and the light-emitting layer 15.
[0243] The hole transport region 12 includes a first layer as described herein. For the description of the first layer, refer to what is described in this specification.
[0244] In addition to the first layer, the hole transport region 12 may further include a hole injection layer, a hole transport layer, a hole injection layer / hole transport layer, a hole injection layer / first hole transport layer / second hole transport layer, a hole injection layer / first hole transport layer / second hole transport layer / electron blocking layer, a hole transport layer / intermediate layer, a hole injection layer / hole transport layer / intermediate layer, a hole transport layer / electron blocking layer, or a hole injection layer / hole transport layer / electron blocking layer.
[0245] The hole transport region 12 contains any compound having hole transport properties.
[0246] For example, the hole transport region 12 contains an amine compound.
[0247] According to one embodiment, the hole transport region 12 may include, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD (Chemical Formula 49), 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), a compound represented by the following Chemical Formula 201 to a compound represented by the following Chemical Formula 205 (Chemical Formula 50 to Chemical Formula 54), or any combination thereof:
[0248]
Chemical Formula
[0249]
Chemical Formula
[0250]
Chemical Formula
[0251]
Chem.
[0252]
Chem.
[0253]
Chem.
[0254] In the chemical formulas 201 to 205, L 201 ~L 209 are, independently of one another, *-O-*’, *-S-*’, a substituted or unsubstituted C5-C 60 carbocyclic group, or a substituted or unsubstituted C1-C 60 heterocyclic group, xa1 to xa9 are, independently of one another, integers from 0 to 5, R 201 ~R 206 are, independently of one another, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic hetero-fused polycyclic group, and among R 201 ~R 206 two adjacent groups are optionally linked to each other via a single bond, a dimethylmethylene group, or a diphenylmethylene group.
[0255] For example, said L 201 ~L 209 is deuterium, a C1-C 10 alkyl group, a C1-C 10 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a triphenylenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, -Si(Q 11 )(Q 12 )(Q 13 ), or a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzoflocarbazole group, a benzothienocarbazole group, or a triindrobenzene group which is substituted or unsubstituted with any combination thereof, xa1 to xa9 are each independently 0, 1 or 2, R 201 ~R 206 are each independently deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a C1-C 10A phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), or a phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, indenocarbazolyl group, indolocarbazolyl group, benzoflocarbazolyl group, or benzothienocarbazolyl group, which is substituted or unsubstituted with any combination thereof, wherein the aforementioned Q 11 ~Q 13 and Q 31 ~Q 33 are each independently C1-C10 an alkyl group, C1-C 10 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.
[0256] According to one embodiment, the hole transport region 12 contains a carbazole-containing amine compound.
[0257] According to another embodiment, the hole transport region 12 contains a carbazole-containing amine compound and a carbazole-free amine compound.
[0258] The carbazole-containing amine compound includes, for example, a compound represented by Chemical Formula 201 that contains a carbazole group and further contains at least one of a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spiro-bifluorene group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, and a benzothienocarbazole group.
[0259] The carbazole-free amine compound includes, for example, a compound represented by Chemical Formula 201 that does not contain a carbazole group and contains at least one of a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spiro-bifluorene group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, and a benzothienocarbazole group.
[0260] According to still another embodiment, the hole transport region 12 contains the compound represented by Chemical Formula 201, the compound represented by Chemical Formula 202, or any combination thereof.
[0261] According to one embodiment, the hole transport region 12 contains the compound represented by the following Chemical Formula 201-1 (Chemical Formula 55), 202-1 (Chemical Formula 56), or 201-2 (Chemical Formula 77), or any combination thereof.
[0262]
Chemical Formula
[0263] [Chemical formula]
[0264] [Chemical formula]
[0265] In the chemical formulas 201-1, 202-1, and 201-2, L 201 ~L 203 , L 205 , xa1 to xa3, xa5, R 201 and R 202 The descriptions regarding them shall refer to those described in this specification respectively. R 211 ~R 213 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazo group, C1-C 20 alkyl group, C1-C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, phenyl group substituted with a C1-C 10 alkyl group, phenyl group substituted with -F, naphthyl group, fluorenyl group, spiro-bifluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, triphenylenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, or pyridinyl group.
[0266] For example, the hole transport region 12 may contain one of the following compounds HT1 to HT39 (Chemical formulas 58 to 60), or any combination thereof:
[0267] [Chemical formula]
[0268] [Chemistry]
[0269] [Chemistry]
[0270] On the one hand, the hole transport region 12 of the organic light-emitting element 10 may further contain a p-dopant. When the hole transport region 12 further contains a p-dopant, the hole transport region 12 can have a structure including a matrix (for example, at least one of the compounds represented by the chemical formulas 201 to 205) and the p-dopant contained in the matrix. The p-dopant is doped uniformly or non-uniformly in the hole transport region 12.
[0271] According to one embodiment, the LUMO energy level of the p-dopant is also -3.5 eV or less.
[0272] The p-dopant includes a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof.
[0273] For example, the p-dopant is a quinone derivative such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), F6-TCNNQ; a metal oxide such as tungsten oxide and molybdenum oxide; 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); a compound represented by the following chemical formula 221; or any combination thereof; and may include (the following Chemical Formulas 61 to 62).
[0274] [Chemistry]
[0275] [ka]
[0276] In the above formula 221, R 221 ~R 223 are each independently a substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C1-C 60 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, 221 ~R 223 At least one of the substituents is a C1-C substituted with a cyano group; -F; -Cl; -Br; -I; -F 20 Alkyl groups; C1-C substituted with -Cl 20 Alkyl groups; C1-C substituted with -Br 20 Alkyl groups; C1-C substituted with -I 20 an alkyl group; or any combination thereof;
[0277] The compound represented by the above chemical formula 221 includes, for example, the following compound HT-D2 (chemical formula 63).
[0278] [ka]
[0279] The thickness of the hole transport region 12 is from about 100 Å to about 10,000 Å, for example, from about 400 Å to about 2,000 Å, and the thickness of the light-emitting layer 15 is from about 100 Å to about 3,000 Å, for example, from about 300 Å to about 1,000 Å. When the thicknesses of the hole transport region 12 and the light-emitting layer 15 satisfy the above-mentioned ranges, hole transport characteristics and / or light-emitting characteristics to be satisfied can be obtained without substantial increase in driving voltage.
[0280] The hole transport region 12 may further include a buffer layer.
[0281] The buffer layer can play a role of compensating for the optical resonance distance according to the wavelength of light emitted from the light-emitting layer and increasing the efficiency.
[0282] The hole transport region 12 may further include an electron blocking layer. The electron blocking layer contains a known substance, for example, mCP or DBFPO (Chemical Formula 64):
[0283]
Chemical Formula
[0284] [Electron transport region 17] In the organic light-emitting device 10, an electron transport region 17 is disposed between the light-emitting layer 15 and the second electrode 19.
[0285] The electron transport region 17 can have a single-layer structure or a multilayer structure.
[0286] For example, the electron transport region 17 can have a structure of an electron transport layer, an electron transport layer / electron injection layer, a buffer layer / electron transport layer, a hole blocking layer / electron transport layer, a buffer layer / electron transport layer / electron injection layer, or a hole blocking layer / electron transport layer / electron injection layer. The electron transport region 17 may further include an electron control layer.
[0287] The electron transport region 17 contains a known electron transport material.
[0288] The electron transport region 17 (for example, in the electron transport region, a buffer layer, a hole blocking layer, an electron modulation layer, or an electron transport layer) contains a metal-free compound containing at least one π-electron-deficient nitrogen-containing C1-C 60 cyclic group. For the description of the π-electron-deficient nitrogen-containing C1-C 60 cyclic group, refer to what is described in this specification.
[0289] For example, the electron transport region 17 may contain a compound represented by the following Chemical Formula 601 (Chem. 65).
[0290]
Chemical Formula
[0291] In the Chemical Formula 601, Ar 601 and L 601 are each independently a C5-C 601a carbocyclic group which is substituted or unsubstituted with at least one R 60 or a C1-C 601a heterocyclic group which is substituted or unsubstituted with at least one R 60 , xe11 is 1, 2 or 3, xe1 is an integer from 0 to 5, R 601a and R 601 are each independently a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60A heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group, -Si(Q 601 )(Q 602 )(Q 603 ), -C(=O)(Q 601 ), -S(=O)2(Q 601 ), or -P(=O)(Q 601 )(Q 602 ), wherein said Q 601 ~Q 603 are, independently of each other, a C1-C 10 alkyl group, a C1-C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, xe21 is an integer from 1 to 5.
[0292] According to one embodiment, at least one of the xe11 Ar 601 and xe21 R 601 contains a π-electron-deficient nitrogen-containing C1-C 60 cyclic group as described above.
[0293] According to one embodiment, in the chemical formula 601, the ring Ar 601 and L 601 are, independently of each other, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -S(=O)2(Q 31 ), -P(=O)(Q 31 )(Q 32) or any combination thereof, a benzene group, naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphene group, indenopyrene 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, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, or azacarbazole group, which is substituted or unsubstituted, said Q 31 ~Q 33 are, independently of one another, C1-C 10 alkyl group, C1-C 10 alkoxy group, phenyl group, biphenyl group, terphenyl group, or naphthyl group.
[0294] In the chemical formula 601, when xe11 is 2 or more, two or more Ars 601 are linked to each other via a single bond.
[0295] According to another embodiment, in the chemical formula 601, Ar 601 is an anthracene group.
[0296] According to still another embodiment, the compound represented by the chemical formula 601 is represented by the following chemical formula 601-1 (Chemical Formula 66).
[0297]
Chemical Formula
[0298] In the formula (601-1), X 614 is N or C(R 614 ), X 615 is N or C(R 615 ), X 616 is N or C(R 616 ), X 614 ~X 616 at least one of which is N, L 611 ~L 613 are each independently referred to the description of the L 601 above, xe611~xe613 are each independently referred to the description of the xe1 above, R 611 ~R 613 are each independently referred to the description of the R 601 above, R 614 ~R 616 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 alkyl group, C1-C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, or naphthyl group.
[0299] According to another embodiment, in the formulas (601) and (601-1), xe1 and xe611~xe613 are each independently 0, 1 or 2.
[0300] According to yet another embodiment, in the formulas (601) and (601-1), R 601 and R 611 ~R 613 are each independently deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 alkyl group, C1-C 20An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, or a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, which is substituted or unsubstituted with any combination thereofa benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, or an azacarbazolyl group; or, -S(=O)2(Q 601 ) or -P(=O)(Q 601 )(Q 602 ); and for the description of said Q 601 and Q 602 refer to that described in this specification.
[0301] The electron transport region 17 may contain one of the following compounds ET1 to ET36 (Chemical Formula 67 to Chemical Formula 69), or any combination thereof:
[0302]
Chemical Formula
[0303]
Chemical Formula
[0304]
Chemical Formula
[0305] Alternatively, the electron transport region 17 may include 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), NTAZ, DBFPO, or any combination thereof (see Chemical Formula 70 below). For example, when the electron transport region 17 includes a hole blocking layer, the hole blocking layer may include BCP or Bphen.
[0306]
Chemical Formula
[0307] The thicknesses of the buffer layer, the hole blocking layer, or the electron adjusting layer are, independently of each other, about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å. When the thicknesses of the buffer layer, the hole blocking layer, or the electron adjusting layer satisfy the ranges as described above, excellent hole blocking characteristics or electron adjusting characteristics can be obtained without a substantial increase in the driving voltage.
[0308] The thickness of the electron transport layer is about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer satisfies the range as described above, electron transport characteristics to be satisfied can be obtained without a substantial increase in the driving voltage.
[0309] The electron transport region 17 (for example, the electron transport layer in the electron transport region) may further include a metal-containing substance in addition to the substances as described above.
[0310] The metal-containing substance includes an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ions of the alkali metal complex include Li ions, Na ions, K ions, Rb ions, Cs ions, or any combination thereof, and the metal ions of the alkaline earth metal complex include Be ions, Mg ions, Ca ions, Sr ions, Ba ions, or any combination thereof. The ligands coordinated to the metal ions of the alkali metal complex and the alkaline earth metal complex are, independently of each other, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0311] For example, the metal-containing substance may include a Li complex. The Li complex may include, for example, the following compound ET-D1(Liq) or ET-D2 (Chemical Formula 71).
[0312] [Chemical Formula]
[0313] The electron transport region 17 may include an electron injection layer that facilitates injection of electrons from the second electrode 19. The electron injection layer can be in direct contact with the second electrode 19.
[0314] The electron injection layer can have: i) a single-layer structure consisting of a single layer containing a single substance; ii) a single-layer structure consisting of a single layer containing a plurality of different substances; or iii) a multilayer structure consisting of a plurality of layers containing a plurality of different substances.
[0315] The electron injection layer may contain 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.
[0316] The alkali metal includes Li, Na, K, Rb, Cs, or any combination thereof. According to one embodiment, the alkali metal is Li, Na, or Cs. According to another embodiment, the alkali metal is Li or Cs.
[0317] The alkaline earth metal includes Mg, Ca, Sr, Ba, or any combination thereof.
[0318] The rare earth metal includes Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0319] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may include oxides of the alkali metal, the alkaline earth metal, and the rare earth metal, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), or any combination thereof.
[0320] The alkali metal compound includes one of alkali metal oxides such as Li2O, Cs2O, K2O, one of alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, or any combination thereof. According to one embodiment, the alkali metal compound includes LiF, Li2O, NaF, LiI, NaI, CsI, KI, or any combination thereof.
[0321] The alkaline earth metal compound is BaO, SrO, CaO, Ba x Sr 1-x O(0 < x < 1), Ba x Ca 1-xIt contains one of the alkaline earth metal compounds such as O(0 < x < 1), or any combination thereof. According to one embodiment, the alkaline earth metal compound contains BaO, SrO, CaO, or any combination thereof.
[0322] The rare earth metal compound contains YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3, TbF3, or any combination thereof. According to one embodiment, the rare earth metal compound contains YbF3, ScF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof.
[0323] The alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex contain ions of the alkali metal, alkaline earth metal, and rare earth metal as described above. The ligands coordinated to the metal ions of the alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex are, independently of each other, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0324] The electron injection layer may consist only of 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 as described above, and may further contain the organic substance. When the electron injection layer further contains an organic substance, the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof is uniformly or non-uniformly dispersed in the matrix containing the organic substance.
[0325] The thickness of the electron injection layer is about 1 Å to about 100 Å, about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the range as described above, electron injection characteristics to be satisfied can be obtained without a substantial increase in driving voltage.
[0326] [Second Electrode 19] A second electrode 19 is disposed on the upper part of the intermediate layer 10A as described above. The second electrode 19 is a cathode which is an electron injection electrode. At this time, as the material for the second electrode 19, a metal, an alloy, an electrically conductive compound, or a combination thereof having a low work function can be used.
[0327] The second electrode 19 may contain lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, IZO, or any combination thereof. The second electrode 19 is a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0328] The second electrode 19 can have a single-layer structure which is a single layer or a multilayer structure including a plurality of layers.
[0329] Explanation regarding terms In this specification, C1-C60 The alkyl group means a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, C1-C 60 The alkylene group is the C1-C 60 means a divalent group having the same structure as the alkyl group.
[0330] In this specification, C1-C 60 alkyl group, C1-C 20 alkyl group and / or C1-C 10 Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec-decyl group, tert-decyl group, or a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec-decyl group, or tert-decyl group, etc., which are substituted or unsubstituted and any combination thereof.
[0331] In this specification, C1-C 60 The alkoxy group is -OA 101 (where A 101 is the C1-C60 It means a monovalent group having a chemical formula of (being an alkyl group), and specific examples thereof include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or a pentoxy group, etc.
[0332] In this specification, C2-C 60 An alkenyl group has a structure containing one or more carbon-carbon double bonds in the middle or at the end of the above C2-C 60 alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, a butenyl group, etc. In this specification, C2-C 60 An alkenylene group means a divalent group having the same structure as the above alkenyl group. 60 An alkenylene group means a divalent group having the same structure as the above alkenyl group.
[0333] In this specification, C2-C 60 An alkynyl group has a structure containing one or more carbon-carbon triple bonds in the middle or at the end of the above C2-C 60 alkyl group, and specific examples thereof include an ethynyl group, a propynyl group, etc. In this specification, C2-C 60 An alkynylene group means a divalent group having the same structure as the above alkynyl group. 60 An alkynylene group means a divalent group having the same structure as the above alkynyl group.
[0334] In this specification, C3-C 10 A cycloalkyl group means a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, C3-C 10 A cycloalkylene group means a divalent group having the same structure as the above C3-C 10 cycloalkyl group.
[0335] In this specification, C3-C 10 Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, etc.
[0336] In this specification, C1-C 10 The heterocycloalkyl group means a monovalent monocyclic group having 1 to 10 carbon atoms and containing at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, and C1-C 10 The heterocycloalkylene group means a divalent group having the same structure as the above C1-C 10 heterocycloalkyl group.
[0337] In this specification, C1-C 10 Examples of the heterocycloalkyl group include a silolanyl group, a silinanil group, a tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, a tetrahydrothiophenyl group, and the like.
[0338] In this specification, C3-C 10 The cycloalkenyl group means a monovalent cyclic group having 3 to 10 carbon atoms and having at least one carbon-carbon double bond in the ring but not having aromaticity, and specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. In this specification, C3-C 10 The cycloalkenylene group means a divalent group having the same structure as the above C3-C 10 cycloalkenyl group.
[0339] In this specification, C1-C 10 The heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms and containing at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, and having at least one double bond in the ring. The above C1-C 10 Specific examples of the heterocycloalkenyl group include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. In this specification, C1-C 10 The heterocycloalkenylene group means a divalent group having the same structure as the above C1-C 10 heterocycloalkenyl group.
[0340] In this specification, C6-C 60An aryl group means a monovalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms, C6-C 60 An arylene group means a divalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms. The C6-C 60 Specific examples of the aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a chrysenyl group, etc. The C6-C 60 The aryl group and the C6-C 60 When the arylene group contains two or more rings, the two or more rings may be fused to each other.
[0341] In this specification, C1-C 60 A heteroaryl group means a monovalent group containing at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and having a heterocyclic aromatic system with 1 to 60 carbon atoms, C1-C 60 A heteroarylene group means a divalent group containing at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom and having a heterocyclic aromatic system with 1 to 60 carbon atoms. The C1-C 60 Specific examples of the heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, etc. The C1-C 60 The heteroaryl group and the C1-C 60 When the heteroarylene group contains two or more rings, the two or more rings may be fused to each other.
[0342] In this specification, C6-C 60 An aryloxy group is -OA 102 (where A 102 is the C6-C 60 aryl group), and the C6-C 60 An arylthio group is -SA 103 (where A 103 is the C6-C 60 aryl group).
[0343] As used herein, a monovalent non-aromatic condensed polycyclic group means a monovalent group in which two or more rings are condensed with each other, containing only carbon as ring-forming atoms (for example, having 8 to 60 carbon atoms), and the whole molecule having non-aromaticity. Specific examples of the non-aromatic condensed polycyclic group include a fluorenyl group and the like. As used herein, a divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
[0344] As used herein, a monovalent non-aromatic hetero-condensed polycyclic group means a monovalent group in which two or more rings are condensed with each other, containing, in addition to carbon (for example, having 1 to 60 carbon atoms), a hetero atom selected from N, O, P, Si, S, Se, Ge, and B as ring-forming atoms, and the whole molecule having non-aromaticity. The monovalent non-aromatic hetero-condensed polycyclic group includes a carbazolyl group and the like. As used herein, a divalent non-aromatic hetero-condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic hetero-condensed polycyclic group.
[0345] As used herein, the “nitrogen-containing C1-C 60 cyclic group with π-electron deficiency” is a cyclic group having 1 to 60 carbon atoms and containing at least one *-N=*’ (where * and *’ are respectively bonding sites with adjacent atoms) as a ring-constituting moiety. For example, it is a) a first ring, b) a condensed ring in which two or more first rings are condensed with each other, or c) a condensed ring in which one or more first rings and one or more second rings are condensed with each other.
[0346] As used herein, the “C3-C 60 cyclic group with π-electron excess” is a cyclic group having 3 to 60 carbon atoms and not containing *-N=*’ (where * and *’ are respectively bonding sites with adjacent atoms) as a ring-constituting moiety. For example, it is a) a second ring, or b) a condensed ring in which two or more second rings are condensed with each other.
[0347] As used herein, the “C5-C 60 cyclic group” is a monocyclic group or polycyclic group having 5 to 60 carbon atoms. For example, it is a) a third ring, or b) a condensed ring in which two or more third rings are condensed with each other.
[0348] In this specification, "C1-C 60 heterocyclic group" is a monocyclic or polycyclic group having 1 to 60 carbon atoms containing at least one heteroatom, for example, a) a fourth ring, b) a condensed ring in which two or more fourth rings are condensed with each other, or c) a condensed ring in which one or more third rings and one or more fourth rings are condensed with each other.
[0349] In this specification, the "first ring" is an imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, triazole group, tetrazole group, oxadiazole group, triazine group, or thiadiazole group.
[0350] In this specification, the "second ring" is a benzene group, cyclopentadiene group, pyrrole group, furan group, thiophene group, or silole group.
[0351] In this specification, the "third ring" is a cyclopentane group, cyclopentadiene group, indene group, adamantane group, norbornene group, bicyclo[1.1.1]pentane group, bicyclo[2.1.1]hexane group, bicyclo[2.2.1]heptane group (norbornane group), bicyclo[2.2.2]octane group, cyclohexane group, cyclohexene group, or benzene group.
[0352] In this specification, the "fourth ring" is a furan group, thiophene group, pyrrole group, silole group, oxazole group, isoxazole group, oxadiazole group, isoxadiazole group, oxatriazole group, isoxatriazole group, thiazole group, isothiazole group, thiadiazole group, isothiadiazole group, thiatriazole group, isothiatriazole group, pyrazole group, imidazole group, triazole group, tetrazole group, azasilole group, diazasilole group, triazasilole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, or triazine group.
[0353] For example, the π-electron-deficient nitrogen-containing C1-C 60 cyclic group is an imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, benzoquinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzosilole group, acridine group, or pyridopyrazine group.
[0354] For example, the π-electron-excessive C3-C 60The cyclic group is a benzene group, heptalene group, indene group, naphthalene group, azulene group, indacene group, acenaphthylene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentacene group, hexacene group, pentaphene group, rubicene group, coronene group, ovalene group, pyrrole group, furan group, thiophene group, isoindole group, indole group, indene group, benzofuran group, benzothiophene group, benzosilole group, naphthopyrrole group, naphthofuran group, naphthothiophene group, naphthosilole group, benzocarbazole group, dibenzocarbazole group, dibenzofuran group, dibenzothiophene group, carbazole group, dibenzosilole group, indenocarbazole group, indolocarbazole group, benzofluorocarbazole group, benzothienocarbazole group, benzosilolocarbazole group, triindrobenzene group, pyrrolophenanthrene group, furanophenanthrene group, thienophenanthrene group, benzonaphthofuran group, benzonaphthothiophene group, (indolo)phenanthrene group, (benzofurano)phenanthrene group, or (benzothieno)phenanthrene group.
[0355] For example, the C5-C 60 The carbocyclic group is a cyclopentane group, cyclohexane group, cyclohexene group, benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, 1,2,3,4-tetrahydronaphthalene group, cyclopentadiene group, indene group, fluorene group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, adamantane group, norbornane group, or norbornene group.
[0356] For example, the C1-C 60The heterocyclic group is a thiophene group, a furan group, a pyrrole group, a cyclopentadiene group, a silole group, a borole group, a phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, or a benzothiadiazole group.
[0357] As used herein, the "N-carbazolyl group" is a monovalent group in which hydrogen is separated from N of the carbazole group and can be bonded to another group, and is represented by the following Chemical Formula 72 (where * is a bonding site with an adjacent atom).
[0358]
Chemical Formula
[0359] In this specification, each of the π-electron-deficient nitrogen-containing C1-C 60 cyclic group, π-electron-excessive C3-C 60 cyclic group, C5-C 60 cyclic group, and C1-C 60 heterocyclic group is, depending on the chemical formula structure, part of a condensed ring or a monovalent, divalent, trivalent, tetravalent, pentavalent, or hexavalent group.
[0360] In this specification, each of the aforementioned substituted π-electron-deficient nitrogen-containing C1-C 60 cyclic group, substituted π-electron-excessive C3-C 60 cyclic group, substituted C5-C 60 cyclic group, substituted C1-C 60 heterocyclic group, substituted C1-C 60 alkylene group, substituted C2-C 60 alkenylene group, substituted C2-C 60 alkynylene group, substituted C3-C 10 cycloalkylene group, substituted C1-C 10 heterocycloalkylene group, substituted C3-C 10 cycloalkenylene group, substituted C1-C 10 heterocycloalkenylene group, substituted C6-C 60 arylene group, substituted C1-C 60 heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic hetero-condensed polycyclic group, substituted C1-C 60 alkyl group, substituted C2-C 60 alkenyl group, substituted C2-C 60 alkynyl group, substituted C1-C 60 alkoxy group, substituted C3-C 10 cycloalkyl group, substituted C1-C 10 heterocycloalkyl group, substituted C3-C 10 cycloalkenyl group, substituted C1-C 10 heterocycloalkenyl group, substituted C6-C 60 aryl group, substituted C6-C 60An aryloxy group, a substituted C6-C 60 An arylthio group, a substituted C1-C 60 The substituents of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic hetero-condensed polycyclic group are, independently of one another, Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, or C1-C 60 Alkoxy group; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C7-C 60 Alkylaryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, C2-C 60 Alkylheteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero-condensed polycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-Ge(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q19 ), -P(Q 18 )(Q 19 ), or a C1-C alkyl group, a C2-C alkenyl group, a C2-C alkynyl group, or a C1-C alkoxy group, replaced by any combination thereof; 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, or C1-C 60 alkoxy group; deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C7-C 60 alkylaryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, C2-C 60 alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic hetero-condensed polycyclic group, -N(Q 21 )(Q 22 ), -Si(Q 23 )(Q 24 )(Q 25 ), -Ge(Q 23 )(Q 24 )(Q 25 ), -B(Q 26 )(Q 27 ), -P(=O)(Q 28 )(Q 29 ), -P(Q 28 )(Q 29 ), or a C3-C group substituted or unsubstituted by any combination thereof; 10Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C7-C 60 Alkylaryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, C2-C 60 Alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic hetero-condensed polycyclic group; -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-Ge(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 )、or -P(Q 38 )(Q 39 ); or any combination thereof; and
[0361] In this specification, Q1 to Q9, Q 11 ~Q 19 、Q 21 ~Q 29 、and Q 31 ~Q 39 are, independently of one another, hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; amidino group; hydrazine group; hydrazone group; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphoric acid group or its salt; deuterium, C1-C 60 alkyl group, C6-C 60 aryl group, or a C1-C 60 alkyl group which is substituted or unsubstituted with any combination thereof; C2-C 60 alkenyl group; C2-C 60 alkynyl group; C1-C 60alkoxy group; C3-C 10 cycloalkyl group; C1-C 10 heterocycloalkyl group; C3-C 10 cycloalkenyl group; C1-C 10 heterocycloalkenyl group; deuterium, C1-C 60 alkyl group, C6-C 60 aryl group, or a C6-C substituted or unsubstituted with any combination thereof 60 aryl group; C6-C 60 aryloxy group; C6-C 60 arylthio group; C1-C 60 heteroaryl group; monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic hetero-condensed polycyclic group; is.
[0362] For example, in this specification, Q1 to Q9, Q 11 ~Q 19 、Q 21 ~Q 29 、and Q 31 ~Q 39 are, independently of one another, -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or deuterium, C1-C 10 alkyl group, phenyl group, or an n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, phenyl group, biphenyl group, or naphthyl group substituted or unsubstituted with any combination thereof; is.
[0363] In this specification, "room temperature" means a temperature of about 25 °C.
[0364] In this specification, "biphenyl group, terphenyl group, and tetraphenyl group" each mean a monovalent group in which two, three, or four phenyl groups are linked to each other via single bonds.
[0365] Hereinafter, synthesis examples and implementation examples will be given to more specifically explain the compounds and organic light-emitting devices according to an embodiment of the present invention. However, the present invention is not limited to the following synthesis examples and implementation examples. In the following synthesis examples, in the expression "using 'B' instead of 'A'", the usage amount of "B" and the usage amount of "A" are the same on a molar equivalent basis.
[0366] [Examples] Evaluation Example 1 The HOMO energy level, LUMO energy level, dipole moment, and T1 energy of the compounds (Chemical Formula 73 and Chemical Formula 74) described in Table 1 below were evaluated using the DFT method (T1 adiabatic) of the Gaussian program with structural optimization at the B3LYP / 6-31G(d,p) level, and the results were tabulated in Table 1.
[0367]
Table 1
[0368]
Chemical Formula
[0369]
Chemical Formula
[0370] Fabrication of OLED A1 A glass substrate with a 1500 Å thick ITO (Indium tin oxide) electrode (first electrode, anode) was cleaned with ultrasonic distilled water. After the cleaning with distilled water was completed, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, and after drying, it was transferred to a plasma cleaner and the substrate was cleaned with oxygen plasma for 5 minutes, and then the substrate was transferred to a vacuum laminator.
[0371] Compound HT1 and compound HT-D2 (see Chemical Formula 75 below) were co-evaporated on the ITO electrode of the glass substrate at a weight ratio of 98:2 to form a 100 Å thick hole injection layer. After that, compound HT3 (see Chemical Formula 75 below) was evaporated on the hole injection layer to form a 1300 Å thick hole transport layer. The first substance described in Table 2 was evaporated on the hole transport layer to form a 50 Å thick first layer, forming a hole transport region.
[0372] A first compound, a second compound, and an organometallic compound (weight ratio of first compound: second compound: organometallic compound is 57:30:13) were co-evaporated on the hole transport region to form a 400 Å thick light-emitting layer. H1, E1, and P31 were used as the first compound, the second compound, and the organometallic compound (emitter), respectively.
[0373] BCP (see Chemical Formula 75 below) was vacuum-evaporated on the light-emitting layer to form a 100 Å thick hole-blocking layer. Compound ET27 (see Chemical Formula 75 below) and Liq were co-evaporated on the hole-blocking layer at a volume ratio of 50:50 to form a 300 Å thick electron transport layer. After that, Liq was evaporated on the electron transport layer to form a 10 Å thick electron injection layer, and a 1200 Å thick Al second electrode (cathode) was formed on the electron injection layer to fabricate an organic light-emitting device.
[0374]
Chemical Formula
[0375] Fabrication of OLEDs A2 to A14 An organic light-emitting device was fabricated using a method similar to that for fabricating the OLED A1, except that the compound described in Table 2 was used as the first substance during the formation of the first layer.
[0376] Evaluation Example 2 The capacitance (F) - voltage (V) curves of each of the OLED A1 to OLED A14 were evaluated using FLUXIM PAIOS (measured in 80 steps by applying an AC amplitude of 0.1 V in the DC current range of -2V to 6V and fixing the measurement frequency at 500 Hz), and then the maximum capacitance value (Cmax) of each of the OLED A1 to OLED A14 was obtained. After that, the maximum capacitance values of each of the OLED A2 to OLED A14 are shown in Table 2 as relative values (%) with respect to the maximum capacitance value of the OLED A1. Also, the capacitance - voltage curves of the OLED A4 and OLED A9 are shown in Figure 2.
[0377]
Table 2
[0378] From Table 2 and Figure 2, it can be confirmed that the maximum capacitance values of the OLED A5 to OLED A14, which are examples, decreased compared to the maximum capacitance values of the OLED A1 to OLED A4, which are comparative examples.
[0379] Fabrication of OLEDs B1 to B14 An organic light-emitting device was fabricated using a method similar to that for each of the OLED A1 to OLED A14, except that during the formation of the light-emitting layer, the first compound, the second compound, the thermally activated delayed fluorescence substance, and the organometallic compound (the weight ratio of the first compound: the second compound: the thermally activated delayed fluorescence substance: the organometallic compound is 56:30.2:13:0.8) were co-evaporated to form a 400 Å thick light-emitting layer. H1, E1, D3, and P31 were used as the first compound, the second compound, the thermally activated delayed fluorescence substance (emitter), and the organometallic compound (sensitizer), respectively.
[0380] Evaluation Example 3 After obtaining the capacitance-voltage curves and the maximum capacitance (Cmax) of each of the OLEDs B1 to B14 in the same manner as in Evaluation Example 2, the maximum capacitance values of each of the OLEDs B2 to B14 were tabulated in Table 3 as relative values (%) with respect to the maximum capacitance value of the OLED B1.
[0381]
Table 3
[0382] From Table 3, it can be confirmed that the maximum capacitance values of the OLEDs B5 to B14, which are the examples, are lower than the maximum capacitance values of the OLEDs B1 to B4, which are the comparative examples.
Explanation of Reference Numerals
[0383] 10A Intermediate Layer 11 First Electrode 12 Hole Transport Region 15 Light-Emitting Layer 17 Electron Transport Region 19 Second Electrode
Claims
1. a first electrode, a second electrode facing the first electrode, an intermediate layer disposed between the first electrode and the second electrode, comprising: the intermediate layer includes a light-emitting layer and a hole transport region, the hole transport region includes a first layer, the first layer is disposed between the first electrode and the light-emitting layer, the light-emitting layer includes a host and an organometallic compound, the organometallic compound includes a transition metal, the host includes a first compound, the first layer includes a first material, satisfying one of the following <Condition 1> or <Condition 2>: <Condition 1> ΔHOMO is less than 0 eV, and the dipole moment of the first material is less than 3.0 debye; <Condition 2> ΔHOMO is greater than 0 eV, and the dipole moment of the first material is 3.0 debye or more; in the above <Condition 1> and <Condition 2>, the ΔHOMO is a value obtained by subtracting the HOMO energy level of the first compound from the HOMO energy level of the first material, each of the HOMO energy level of the first compound, the HOMO energy level of the first material, and the dipole moment of the first material is calculated based on Density Functional Theory (DFT), the HOMO energy level of the first compound and the HOMO energy level of the first material are negative numbers, a light-emitting device.
2. satisfying the above <Condition 1>, ΔHOMO is -0.5 eV or more and less than 0 eV, the light-emitting device according to Claim 1.
3. satisfying the above <Condition 1>, the dipole moment of the first material is 0.5 debye or more and less than 3.0 debye, the light-emitting device according to Claim 1.
4. satisfying the above <Condition 2>, ΔHOMO is more than 0 eV and 0.1 eV or less, the light-emitting device according to Claim 1.
5. satisfying the above <Condition 2>, the dipole moment of the first material is 3.0 debye or more and 6.0 debye or less, the light-emitting device according to Claim 1.
6. the HOMO energy level of the first compound is -5.6 eV to -4.8 eV, the light-emitting device according to Claim 1.
7. The triplet (T 1 ) energy level of the first compound is 2.8 eV or more, and the light-emitting element according to claim 1.
8. the HOMO energy level of the first material is -5.6 eV to -4.8 eV, the light-emitting device according to Claim 1.
9. The light-emitting device according to claim 1, wherein the dipole moment of the first substance is 0.8 debye to 7.0 debye.
10. The organometallic compound further includes n ligands bonded to the transition metal, The transition metal is platinum (Pt) or palladium (Pd), The n is 1, The light-emitting device according to claim 1, wherein the ligand is a tetradentate ligand.
11. The light-emitting device according to claim 10, wherein the tetradentate ligand includes a carbene moiety bonded to the transition metal.
12. The host of the light-emitting layer further includes a second compound, The second compound is different from the first compound, The light-emitting device according to claim 1, wherein the first compound is a hole-transporting compound and the second compound is an electron-transporting compound.
13. The light-emitting device according to claim 1, wherein the light-emitting layer emits blue light.
14. The light-emitting device according to claim 1, wherein the organometallic compound is an emitter.
15. The light-emitting device according to claim 14, wherein the organometallic compound emits blue light.
16. The light-emitting device according to claim 1, wherein the light-emitting layer further includes a thermally activated delayed fluorescence substance.
17. The thermally activated delayed fluorescence substance is a multiple resonance thermally activated delayed fluorescence substance, The multiple resonance thermally activated delayed fluorescence substance does not contain a transition metal and is a polycyclic compound containing a core in which two or more C 3 -C 60 cyclic groups are condensed with each other. Among the cores, two C 3 -C 60 The light-emitting element according to claim 16, wherein the cyclic groups are condensed with each other while sharing boron (B) or nitrogen (N).
18. The thermally activated delayed fluorescence substance is an emitter, The light-emitting device according to claim 16, wherein the organometallic compound is a sensitizer.
19. The light-emitting device according to claim 18, wherein the thermally activated delayed fluorescence substance emits blue light.
20. An electronic device including the light-emitting device according to any one of claims 1 to 19.