Organic light emitting diode and organic light emitting device comprising the same

Abstract

The present invention relates to an organic light emitting diode and an organic light emitting device each comprising in a light emitting material layer a first compound represented by the following formula, a second compound as a p-type host and a third compound as an n-type host. Thus, the organic light emitting diode and the organic light emitting device have advantages in driving voltage, luminous efficiency and lifetime.

Description

Technical Field

[0001] Cross-reference to related applications

[0002] This application claims priority to Korean Patent Application No. 10-2021-0133079, filed in Korea on October 7, 2021, the entire contents of which are incorporated herein by reference.

[0003] This invention relates to an organic light-emitting diode (OLED), and more specifically, to an OLED with excellent luminous efficiency and luminous lifetime, and an organic light-emitting device including the OLED. Background Technology

[0004] Organic light-emitting diode (OLED) displays, widely used in flat panel displays, are attracting attention as a rapidly growing replacement for liquid crystal displays (LCDs). OLEDs can be formed with a thickness of less than... OLEDs are organic thin films that can achieve unidirectional or bidirectional images through electrode configuration. Furthermore, OLEDs can even be formed on flexible transparent substrates such as plastic substrates, making it easy to realize flexible or foldable display devices. In addition, OLEDs can be driven at lower voltages and offer superior color purity compared to LCDs.

[0005] An OLED comprises an anode, a cathode, and a light-emitting material layer, and the light-emitting material layer comprises a host and a dopant (e.g., an emitter).

[0006] Because fluorescent materials used as dopants utilize only singlet exciton energy during luminescence, they exhibit low luminescence efficiency. Conversely, phosphorescent materials, utilizing both triplet and singlet exciton energies, can exhibit higher luminescence efficiency. However, representative phosphorescent metal complexes show short luminescence lifetimes in commercial applications.

[0007] In addition, the luminous efficiency and luminous lifetime of OLEDs are also affected by the exciton generation efficiency in the host and the energy transfer efficiency from the host to the dopant.

[0008] Therefore, it is necessary to develop materials for luminescent material layers that can improve the luminous efficiency and luminous lifetime of OLEDs. Summary of the Invention

[0009] Therefore, embodiments of the present invention relate to an OLED and an organic light-emitting device that substantially eliminate one or more problems associated with the limitations and disadvantages of the prior art.

[0010] One aspect of the present invention is to provide an OLED and an organic light-emitting device with excellent luminous efficiency and luminous lifetime.

[0011] Additional features and aspects will be set forth in the following description, some of which will be apparent from the description or may be learned by practicing the inventive concepts provided herein. Other features and aspects of the inventive concept may be realized and obtained by means of structures particularly pointed out in the written description or derived therefrom, as well as by the claims and drawings.

[0012] To achieve these and other aspects of the inventive concept, as embodied and broadly described, in one aspect, the present invention provides an organic light-emitting diode (OLED) comprising: a first electrode, a second electrode facing the first electrode, and a first light-emitting portion comprising a first red light-emitting material layer and located between the first and second electrodes, wherein the first red light-emitting material layer comprises a first compound, a second compound, and a third compound, wherein the first compound is represented by formula 1-1:

[0013] [Equation 1-1] Where M is molybdenum (Mo), tungsten (W), rhenium (Re), ruthenium (Ru), osmium (Os), rhodium (Rh), iridium (Ir), palladium (Pd), platinum (Pt), or silver (Ag); A and B are each carbon atoms; R is an unsubstituted or substituted C1-C atom. 20 Alkyl, unsubstituted or substituted C1-C 20 Alkyl silyl, unsubstituted or substituted C3-C 30 Alicyclic group, unsubstituted or substituted C3-C 30 Heterocyclic groups, unsubstituted or substituted C6-C 30 Aromatic groups or unsubstituted or substituted C3-C 30 Mixed aromatic groups; X 1 To X 11 Each independently consists of carbon atoms, CR 1 Or N; can only form with X 3 -X 5 Y 1 and the ring (a) of A or having X 8 -X 11 Y 2 One of the rings (b) with B; if a ring (a) is formed, then X 3 and Y 1 Each is a carbon atom, X 6 and X 7 or X 7 and X 8 Further formation of unsubstituted or substituted C3-C 30 Alicyclic, unsubstituted or substituted C3-C 30 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic rings or unsubstituted or substituted C3-C 30 Mixed aromatic rings; and Y2 It is BR 2 CR 2 R 3 C=O, SiR 2 R 3 GeR 2 R 3 PR 2 ,P=O,O,S,SO2,Se,SeO2,Te,TeO2 or NR a , where R a It is unsubstituted or substituted C1-C 20 Alkyl or unsubstituted or substituted C6-C 30 Aromatic groups; if a ring (b) is formed, then X 8 and Y 2 Each is a carbon atom, X 1 and X 2 or X 2 and X 3 Further formation of unsubstituted or substituted C3-C 30 Alicyclic, unsubstituted or substituted C3-C 30 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic rings or unsubstituted or substituted C3-C 30 Mixed aromatic rings; and Y 1 It is BR 2 CR 2 R 3 C=O, SiR 2 R 3 GeR 2 R 3 PR 2 ,P=O,O,S,SO2,Se,SeO2,Te,TeO2 or NR a , where R a It is unsubstituted or substituted C1-C 20 Alkyl or unsubstituted or substituted C6-C 30 Fangzuji, R 1 To R 3 Each is independently a hydrogen, protium, deuterium, tritium, halogen atom, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, unsubstituted or substituted C1-C group. 20 Alkyl, unsubstituted or substituted C2-C 20 Alkenyl, unsubstituted or substituted C2-C 20 Alkyne group, unsubstituted or substituted C1-C 20 Alkoxy, amino, unsubstituted or substituted C1-C 20 Alkylamino, unsubstituted or substituted C1-C 20Alkyl silyl, carboxyl, nitrile, isonitrile, thioalkyl, phosphine, unsubstituted or substituted C3-C 30 Alicyclic group, unsubstituted or substituted C3-C 30 Heterocyclic groups, unsubstituted or substituted C6-C 30 Aromatic groups or unsubstituted or substituted C3-C 30 Hybrid aromatic bases, optionally, two adjacent R 1 , and / or R 2 and R 3 Further unsubstituted or substituted C3-C 30 Alicyclic, unsubstituted or substituted C3-C 30 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic rings or unsubstituted or substituted C3-C 30 Mixed aromatic rings; It is an auxiliary ligand; m is an integer from 1 to 3; n is an integer from 0 to 2; m+n is the oxidation number of M, where the second compound is represented by Equation 2-1: [Equation 2-1]

[0014] X and Y are each independently selected from deuterated or undeuterated unsubstituted or substituted C6-C. 30 Aryl and deuterated or undeuterated unsubstituted or substituted C3-C 30 The group composed of heteroaryl groups, R 4 Choose C1-C, either unsubstituted or substituted. 10 Alkyl groups and unsubstituted or substituted C6-C 30 The group consisting of aryl groups, where a1 is an integer from 0 to 9, L 1 Choose either deuterated or undeuterated unsubstituted or substituted C6-C. 30 aryl and deuterated or undeuterated unsubstituted or substituted C3-C 30 The group consists of heteroarylene groups, where a2 is 0 or 1, and the third compound is represented by formula 3-1: [Formula 3-1]

[0015] Where M is an oxygen atom (O) or a sulfur atom (S); Q and Z are each independently chosen from unsubstituted or substituted C6-C atoms. 30 Aryl and unsubstituted or substituted C3-C 30 Group composed of heteroaryl groups; L 2 Choose either deuterated or undeuterated unsubstituted or substituted C6-C. 30 aryl and deuterated or undeuterated unsubstituted or substituted C3-C 30 Groups composed of heteroarylene groups; b is 0 or 1.

[0016] On the other hand, the present invention provides an organic light-emitting device, including a substrate and the aforementioned organic light-emitting diode located on or above the substrate.

[0017] It should be understood that the foregoing general description and the following detailed description are exemplary and explanatory, and are intended to provide further explanation of the claimed inventive concept. Attached Figure Description

[0018] The accompanying drawings are incorporated in and constitute a part of this application and are intended to provide a further understanding of the invention, illustrate embodiments of the invention, and, together with the description, serve to explain the principles of the invention.

[0019] Figure 1 This is a schematic circuit diagram illustrating an organic light-emitting display device according to the present invention.

[0020] Figure 2 This is a cross-sectional view showing an organic light-emitting display device according to a first embodiment of the present invention.

[0021] Figure 3 This is a cross-sectional view showing an OLED according to a second embodiment of the present invention.

[0022] Figure 4 This is a cross-sectional view showing an OLED according to a third embodiment of the present invention.

[0023] Figure 5 This is a cross-sectional view showing an organic light-emitting display device according to a fourth embodiment of the present invention.

[0024] Figure 6 This is a cross-sectional view showing an OLED according to a fifth embodiment of the present invention.

[0025] Figure 7 This is a cross-sectional view showing an OLED according to a sixth embodiment of the present invention.

[0026] Figure 8 This is a cross-sectional view showing an OLED according to a seventh embodiment of the present invention. Detailed Implementation

[0027] Reference will now be made in detail to various aspects of the invention, examples of which are shown in the accompanying drawings.

[0028] In this invention, the light-emitting material layer (EML) of the OLED includes dopants (e.g., emitters), n-type hosts, and p-type hosts, each possessing excellent optical properties, thereby giving the OLED advantages in at least one of driving voltage, luminous efficiency, and luminous lifetime. For example, the organic light-emitting device can be an organic light-emitting display device or an organic light-emitting lighting device. The following explanation focuses on organic light-emitting display devices including OLEDs.

[0029] Figure 1 This is a schematic circuit diagram illustrating an organic light-emitting display device according to the present invention.

[0030] like Figure 1 As shown, the organic light-emitting display device includes a gate line GL, a data line DL, a power line PL, a switching thin-film transistor (TFT) Ts, a driving TFT Td, a storage capacitor Cst, and an OLED D. The gate line GL and the data line DL intersect to define a pixel region P. The pixel region may include a red pixel region, a green pixel region, and a blue pixel region.

[0031] The switching TFT Ts is connected to the gate line GL and the data line DL, while the driving TFT Td and the storage capacitor Cst are connected to the switching TFT Ts and the power line PL. The OLED D is connected to the driving TFT Td.

[0032] In an organic light-emitting display device, when the switch TFT Ts is turned on by the gate signal applied through the gate line GL, the data signal from the data line DL is applied to the gate electrode of the driving TFT Td and the electrode of the storage capacitor Cst.

[0033] When the driving TFT Td is turned on by a data signal, current is supplied from the power line PL to the OLED D. As a result, the OLED D emits light. In this case, when the driving TFT Td is turned on, the current level applied from the power line PL to the OLED D is determined so that the OLED D can produce grayscale.

[0034] When the switching TFT Ts is turned off, the storage capacitor Cst is used to maintain the voltage of the gate electrode of the driving TFT Td. Therefore, even when the switching TFT Ts is turned off, the current level applied to the OLED D from the power line PL is maintained until the next frame.

[0035] Therefore, organic light-emitting display devices display the desired image.

[0036] Figure 2 This is a cross-sectional view showing an organic light-emitting display device according to a first embodiment of the present invention.

[0037] like Figure 2 As shown, the organic light-emitting display device 100 includes a substrate 110, a TFT Tr on or above the substrate 110, a planarization layer 150 covering the TFT Tr, and an OLED on the planarization layer 150 and connected to the TFT Tr.

[0038] The substrate 110 can be a glass substrate or a flexible substrate. For example, the flexible substrate can be one of a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylene naphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate, and a polycarbonate (PC) substrate.

[0039] A buffer layer 122 is formed on a substrate, and a TFT Tr is formed on the buffer layer 122. The buffer layer 122 may be omitted. For example, the buffer layer 122 may be formed of an inorganic insulating material, such as silicon oxide or silicon nitride.

[0040] Semiconductor layer 120 is formed on buffer layer 122. Semiconductor layer 120 may include oxide semiconductor material or polysilicon.

[0041] When the semiconductor layer 120 comprises an oxide semiconductor material, a light-shielding pattern (not shown) can be formed beneath the semiconductor layer 120. Light reaching the semiconductor layer 120 is shielded or blocked by the light-shielding pattern, thus preventing thermal degradation of the semiconductor layer 120. On the other hand, when the semiconductor layer 120 comprises polysilicon, impurities can be doped onto both sides of the semiconductor layer 120.

[0042] A gate insulating layer 124 of insulating material is formed on the semiconductor layer 120. The gate insulating layer 124 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride.

[0043] A gate electrode 130, formed of a conductive material such as a metal, is formed on the gate insulating layer 124 corresponding to the center of the semiconductor layer 120. (See reference...) Figure 2 The gate insulating layer 124 is formed on the entire surface of the substrate 110. Alternatively, the gate insulating layer 124 may be patterned to have the same shape as the gate electrode 130.

[0044] An interlayer insulating layer 132 of insulating material is formed on the gate electrode 130 and the entire surface of the substrate 110. The interlayer insulating layer 132 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride, or an organic insulating material such as benzocyclobutene or photopropylene.

[0045] The interlayer insulating layer 132 includes first and second contact holes 134 and 136 exposed on both sides of the semiconductor layer 120. The first and second contact holes 134 and 136 are located on both sides of the gate electrode 130 and spaced apart from the gate electrode 130.

[0046] The first and second contact holes 134 and 136 are formed through the gate insulating layer 124. Alternatively, when the gate insulating layer 124 is patterned to have the same shape as the gate electrode 130, the first and second contact holes 134 and 136 are formed only through the interlayer insulating layer 132.

[0047] Source electrode 144 and drain electrode 146, formed of a conductive material such as metal, are formed on interlayer insulating layer 132.

[0048] The source electrode 144 and the drain electrode 146 are spaced apart from each other relative to the gate electrode 130 and contact the two sides of the semiconductor layer 120 through the first and second contact holes 134 and 136, respectively.

[0049] Semiconductor layer 120, gate electrode 130, source electrode 144, and drain electrode 146 constitute TFT Tr. TFT Tr serves as a driving element. That is, TFT Tr drives TFT Td (… Figure 1 ).

[0050] In the TFT Tr, the gate electrode 130, the source electrode 144, and the drain electrode 146 are located above the semiconductor layer 120. That is, the TFT Tr has a coplanar structure.

[0051] Alternatively, in the TFT Tr, the gate electrode can be located below the semiconductor layer, and the source and drain electrodes can be located above the semiconductor layer, allowing the TFT Tr to have an inverted staggered structure. In this case, the semiconductor layer may include amorphous silicon.

[0052] Although not shown, the gate line and data line intersect to define the pixel area, and the switching TFT is formed to connect to the gate line and the data line. The switching TFT is connected to the TFT Tr, which serves as a driving element. Furthermore, power lines that can be spaced parallel to one of the gate line and data line, and storage capacitors for maintaining the voltage of the gate electrode of the TFT Tr within a frame, may also be formed.

[0053] A planarization layer 150 is formed on the entire surface of the substrate 110 to cover the source electrode 144 and the drain electrode 146. The planarization layer 150 provides a flat top surface and has a drain contact hole 152 that exposes the drain electrode 146 of the TFT Tr.

[0054] OLED D is disposed on planarization layer 150 and includes a first electrode 160 connected to drain electrode 146 of TFT Tr through drain contact hole 152, an organic light-emitting layer 162, and a second electrode 164. Organic light-emitting layer 162 and second electrode 164 are sequentially stacked on first electrode 160. For example, red pixel region, green pixel region, and blue pixel region can be defined on substrate 110, and OLED D is located in each red, green, and blue pixel region. That is, OLEDs emitting red, green, and blue light respectively are located in the red, green, and blue pixel regions respectively.

[0055] First electrodes 160 are formed in each pixel and on the planarization layer 150. The first electrode 160 can be an anode and can be formed of a conductive material with a relatively high work function, such as a transparent conductive oxide (TCO). For example, the first electrode 160 can be formed of indium tin oxide (ITO), indium zinc oxide (IZO), indium tin zinc oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium copper oxide (ICO), or aluminum zinc oxide (Al:ZnO, AZO).

[0056] When the organic light-emitting display device 100 operates in a bottom-emitting mode, the first electrode 160 may have a single-layer structure with a transparent conductive material layer. When the organic light-emitting display device 100 operates in a top-emitting mode, the first electrode 160 may further include a reflective electrode or a reflective layer. For example, the reflective electrode or reflective layer may be formed of a silver (Ag) or aluminum-palladium-copper (APC) alloy. In the top-emitting organic light-emitting display device 100, the first electrode 160 may have a three-layer structure of ITO / Ag / ITO or ITO / APC / ITO.

[0057] A bank layer 166 is formed on the planarization layer 150 to cover the edge of the first electrode 160. That is, the bank layer 166 is located at the boundary of the pixel and exposes the center of the first electrode 160 in the pixel.

[0058] An organic light-emitting layer 162 is formed on the first electrode 160. The organic light-emitting layer 162 may have a monolayer structure of a light-emitting material layer. Alternatively, the organic light-emitting layer 162 may further include at least one of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL) to have a multilayer structure. Furthermore, the organic light-emitting layer 162 may include at least two spaced-apart EMLs to have a tandem structure.

[0059] As shown below, in the OLED D of the red pixel region, the EML in the organic light-emitting layer 162 includes a first compound as a red dopant (emitter), a second compound as a p-type host, and a third compound as an n-type host. Therefore, in the OLED D, the driving voltage is reduced, and the luminous efficiency and luminous lifetime are increased.

[0060] A second electrode 164 is formed on the substrate 110 on which the organic light-emitting layer 162 is formed. The second electrode 164 covers the entire surface of the display area and can be formed of a conductive material with a relatively low work function to serve as a cathode. For example, the second electrode 164 can be formed of aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), or alloys or combinations thereof. In the top-emitting organic light-emitting display device 100, the second electrode 164 can have a thin profile (small thickness) to provide light-transmitting (or semi-transmitting) properties.

[0061] Although not shown, the organic light-emitting display device 100 may also include color filters corresponding to the red, green, and blue pixel regions. For example, red, green, and blue color filter patterns can be formed in the red, green, and blue pixel regions, respectively, thereby improving the color purity of the organic light-emitting display device 100. In the bottom-emitting organic light-emitting display device 100, the color filter may be disposed between the OLED D and the substrate 110, for example, between the interlayer insulating layer 132 and the planarization layer 150. Alternatively, in the top-emitting organic light-emitting display device 100, the color filter may be disposed on or above the OLED D, for example, on or above the second electrode 164.

[0062] An encapsulation film 170 is formed on the second electrode 164 to prevent moisture from penetrating into the OLED D. The encapsulation film 170 includes, but is not limited to, a first inorganic insulating layer 172, an organic insulating layer 174, and a second inorganic insulating layer 176 stacked sequentially. The encapsulation film 170 may be omitted.

[0063] The organic light-emitting display device 100 may also include a polarizer (not shown) for reducing ambient light reflection. For example, the polarizer may be a circular polarizer. In a bottom-emitting organic light-emitting display device 100, the polarizer may be disposed below the substrate 110. In a top-emitting organic light-emitting display device 100, the polarizer may be disposed on or above the encapsulation film 170.

[0064] Furthermore, in the top-emitting organic light-emitting display device 100, a cover window (not shown) can be attached to the encapsulation film 170 or a polarizer. In this case, the substrate 110 and the cover window have flexible properties, thereby providing a flexible organic light-emitting display device.

[0065] Figure 3 This is a cross-sectional view showing an OLED according to a second embodiment of the present invention.

[0066] like Figure 3 As shown, OLED D1 includes a first electrode 160 and a second electrode 164 facing each other, and an organic light-emitting layer 162 between them. The organic light-emitting layer 162 includes a red EML 230.

[0067] Organic light-emitting display device 100 ( Figure 2 It includes red, green and blue pixel areas, and the OLED D1 can be located in the red pixel area.

[0068] The first electrode 160 is the anode for injecting holes, and the second electrode 164 is the cathode for injecting electrons. One of the first electrode 160 and the second electrode 164 is a reflective electrode, while the other of the first electrode 160 and the second electrode 164 is a transparent (semi-transparent) electrode.

[0069] For example, the first electrode 160 may include a transparent conductive material, such as ITO or IZO, and the second electrode 164 may include one of Al, Mg, Ag, AlMg, and MgAg.

[0070] The organic light-emitting layer 162 may further include at least one of an HTL 220 below the red EML 230 and an ETL 240 above or on the red EML 230. That is, the HTL 220 is disposed between the red EML 230 and the first electrode 160, and the ETL 240 is disposed between the red EML 230 and the second electrode 164.

[0071] In addition, the organic light-emitting layer 162 may also include at least one of HIL 210 below HTL 220 and EIL 250 above ETL 240.

[0072] Although not shown, the organic light-emitting layer 162 may also include at least one of an EBL between HTL 220 and red EML 230 and an HBL between ETL 240 and red EML 230.

[0073] In the OLED D1 of the present invention, the red EML 230 can constitute the light-emitting part, or the red EML 230 and at least one of HIL210, HTL 220, EBL, HBL, ETL 240 and EIL 250 can constitute the light-emitting part.

[0074] Red EML 230 includes a first compound 232 as a red dopant, a second compound 234 as a p-type host (e.g., the first host), and a third compound 236 as an n-type host (e.g., the second host). The red EML can have... The thickness, for example

[0075] In red EML 230, the weight percentage of each of the second compound 234 and the third compound 236 is greater than that of the first compound 232. For example, in red EML 230, the first compound 232 may have 1-20% by weight, for example 5-15% by weight.

[0076] Furthermore, in red EML 230, the weight percentage ratio of the second compound 234 to the third compound 236 can be from 1:3 to 3:1. For example, in red EML 230, the second compound 234 and the third compound 236 can have the same weight percentage.

[0077] The first compound 232 is represented by Formula 1-1. The first compound 232 is an organometallic compound with a rigid chemical conformation, which can improve the luminous efficiency and luminous lifetime of OLED D1.

[0078] [Equation 1-1]

[0079]

[0080] in

[0081] M is molybdenum (Mo), tungsten (W), rhenium (Re), ruthenium (Ru), osmium (Os), rhodium (Rh), iridium (Ir), palladium (Pd), platinum (Pt), or silver (Ag);

[0082] A and B are each carbon atoms;

[0083] R is unsubstituted or substituted C1-C 20 Alkyl, unsubstituted or substituted C1-C 20 Alkyl silyl, unsubstituted or substituted C3-C 30 Alicyclic group, unsubstituted or substituted C3-C 30 Heterocyclic groups, unsubstituted or substituted C6-C 30 Aromatic groups or unsubstituted or substituted C3-C 30 Mixed aromatic groups;

[0084] X 1 To X 11 Each independently consists of carbon atoms, CR 1 Or N;

[0085] Only those with X can be formed 3 -X 5 Y 1 and the ring (a) of A or having X 8 -X 11 Y 2 and one of the rings (b) of B; and

[0086] If a ring (a) is formed,

[0087] X 3 and Y 1 Each is a carbon atom.

[0088] X 6 and X 7or X 7 and X 8 Further formation of unsubstituted or substituted C3-C 30 Alicyclic, unsubstituted or substituted C3-C 30 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic rings or unsubstituted or substituted C3-C 30 Mixed aromatic rings; and

[0089] Y 2 It is BR 2 CR 2 R 3 C=O, SiR 2 R 3 GeR 2 R 3 PR 2 ,P=O,O,S,SO2,Se,SeO2,Te,TeO2 or NR a , where R a It is unsubstituted or substituted C1-C 20 Alkyl or unsubstituted or substituted C6-C 30 Aroma base;

[0090] If a ring (b) is formed,

[0091] X 8 and Y 2 Each is a carbon atom.

[0092] X 1 and X 2 or X 2 and X 3 Further formation of unsubstituted or substituted C3-C 30 Alicyclic, unsubstituted or substituted C3-C 30 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic rings or unsubstituted or substituted C3-C 30 Mixed aromatic rings; and

[0093] Y 1 It is BR 2 CR 2 R 3 C=O, SiR 2 R 3 GeR 2 R 3 PR 2 ,P=O,O,S,SO2,Se,SeO2,Te,TeO2 or NR a , where R a It is unsubstituted or substituted C1-C 20 Alkyl or unsubstituted or substituted C6-C30 Fangzuji,

[0094] R 1 To R 3 Each is independently a hydrogen, protium, deuterium, tritium, halogen atom, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, unsubstituted or substituted C1-C group. 20 Alkyl, unsubstituted or substituted C2-C 20 Alkenyl, unsubstituted or substituted C2-C 20 Alkyne group, unsubstituted or substituted C1-C 20 Alkoxy, amino, unsubstituted or substituted C1-C 20 Alkylamino, unsubstituted or substituted C1-C 20 Alkyl silyl, carboxyl, nitrile, isonitrile, thioalkyl, phosphine, unsubstituted or substituted C3-C 30 Alicyclic group, unsubstituted or substituted C3-C 30 Heterocyclic groups, unsubstituted or substituted C6-C 30 Aromatic groups or unsubstituted or substituted C3-C 30 Mixed aromatic compounds, optional

[0095] Two adjacent R 1 , and / or R 2 and R 3 Further formation of unsubstituted or substituted C3-C 30 Alicyclic, unsubstituted or substituted C3-C 30 heterocyclic ring, unsubstituted or substituted C6-C 30 Aromatic rings or unsubstituted or substituted C3-C 30 Mixed aromatic rings;

[0096] It is an auxiliary ligand;

[0097] m is an integer between 1 and 3; and

[0098] n is an integer between 0 and 2;

[0099] m+n is the oxidation number of M.

[0100] As used herein, the term "unsubstituted" means that the specified group does not have substituents and that hydrogen is attached. In this case, hydrogen includes protium, deuterium, and tritium, which are not specifically disclosed.

[0101] As used herein, the substituents in the term "substitution" include, but are not limited to, unsubstituted or halogenated C1-C substituents. 20 Alkyl, unsubstituted or halogenated C1-C 20 Alkoxy, halogen, cyano, -CF3, hydroxy, carboxyl, carbonyl, amino, C1-C 10 Alkylamino, C6-C30 arylamino, C3-C 30 heteroarylamino, C 6- C 30 Aryl, C3-C 30 heteroaryl, nitro, hydrazine, sulfonate, C1-C 20 Alkyl silyl, C1-C 20 Alkoxysilyl, C3-C 20 cycloalkylsilyl, C6-C 30 Arylsilyl and C3-C 30 Heteroarylsilyl group.

[0102] As used herein, the term "alkyl" refers to a branched or unbranched saturated hydrocarbon group having 1 to 20 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, etc.

[0103] As used herein, the term "alkenyl" is a hydrocarbon group consisting of 2 to 20 carbon atoms containing at least one carbon-carbon double bond. Alkenyl groups can be substituted with one or more substituents.

[0104] As used herein, the term "alicyclic" or "cycloalkyl" refers to a non-aromatic carbonyl ring consisting of at least three carbon atoms. Examples of alicyclic groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, etc. Alicyclic groups can be substituted with one or more substituents.

[0105] As used herein, the term "alkoxy" refers to a branched or unbranched alkyl group bonded by an ether bond represented by the formula -O (-alkyl), where alkyl is defined herein. Examples of alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, and tert-butoxy.

[0106] As used herein, the term "alkylamino" refers to a group represented by the formula -NH(-alkyl) or -N(-alkyl)2, where alkyl is defined herein. Examples of alkylamino groups represented by the formula -NH(-alkyl) include, but are not limited to, methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, (sec-butyl)amino, (tert-butyl)amino, pentamino, isopentamino, (tert-pentyl)amino, hexylamino, etc. Examples of alkylamino groups represented by the formula -N(-alkyl)2 include, but are not limited to, dimethylamino, diethylamino, dipropylamino, diisopropylamino, dibutylamino, diisobutylamino, di(sec-butyl)amino, di(tert-butyl)amino, dipentylamino, diisopentylamino, di(tert-pentyl)amino, dihexylamino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-ethyl-N-propylamino, etc.

[0107] As used herein, the terms "aromatic" or "aryl" are well known in the art. This term includes covalently linked monocyclic or fused-ring polycyclic groups. Aromatic groups can be unsubstituted or substituted. Examples of aromatic or aryl groups include phenyl, 1-naphthyl, 2-naphthyl, 4-biphenyl, anthraceneyl, and phenanthrene, etc. Substituents in each of the above aromatic ring systems are acceptable substituents as defined herein.

[0108] As used herein, the term "alkylsilyl" refers to any straight-chain or branched, saturated or unsaturated acyclic or acyclic alkyl group having 1-20 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, trimethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl.

[0109] As used in this article, the term "halogen" refers to a fluorine, chlorine, bromine, or iodine atom.

[0110] As used herein, the term "hetero" in terms such as "heteroaromatic ring," "heterocyclic alkylene," "heteroarylene," "heteroaryl alkylene," "heteroaryl oxylene group," "heterocyclic alkyl," "heteroaryl," "heteroaryl alkyl," "heteroaryloxy," "heteroaryl amino," and "heteroaryl silyl" means that at least one carbon atom (e.g., 1-5 carbon atoms) constituting an aromatic or alicyclic ring is substituted by at least one heteroatom selected from N, O, S, Si, Se, P, B, and combinations thereof.

[0111] As used herein, the term "heteroaromatic" or "heteroaryl" refers to a heterocycle that includes a heteroatom selected from N, O, and S in the ring system, wherein the ring system is an aromatic ring. The term includes covalently linked monocyclic or fused-ring polycyclic groups. Heteroaromatic groups can be unsubstituted or substituted. Examples of heteroaromatic or heteroaryl groups include pyridyl, pyrroleyl, pyrazinyl, pyrimidinyl, thiopheneyl (or thiophene group), thiazolyl, furanyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, oxadiazolyl, thiazolyl, and thiadiazolyl.

[0112] As used herein, the term “heteroaryloxy” refers to a group represented by the formula -O-(heteroaryl), where heteroaryl is defined herein.

[0113] For example, when R and R in equation 1-1 1 To R 3 Each independently is C6-C 30 When aromatic groups are present, R and R 1 To R 3 Each is independently selected from, but not limited to, C6-C30 Aryl, C7-C 30 Aryl group, C6-C 30 aryloxy groups and C6-C 30 The group consisting of aromatic amino groups. For example, when R and R 1 To R 3 Each independently is C6-C 30 In the aryl form, R and R 1 To R 3 Each aryl group is independently selected from, but is not limited to, unfused or fused aryl groups, such as phenyl, biphenyl, terphenyl, naphthyl, anthracene, pentalenyl, indenyl, indeno-indenyl, heptalenyl, biphenylenyl, indacenyl, phenalenyl, phenanthrenyl, benzo-phenanthrenyl, dibenzo-phenanthrenyl, azulenyl, pyrenyl, fluoranthenyl, and triphenylenyl. Chrysenyl, tetraphenylenyl, tetracenyl, pleiadenyl, picenyl, pentaphenylenyl, pentaphenylenyl, fluorenyl, indeno-fluorenyl, and spirofluorenyl.

[0114] Or, when R and R in equation 1 1 To R 3 Each independently constitutes C3-C 30 When the aromatic gene is mixed, R and R 1 To R 3 Each is independently selected from, but not limited to, C3-C 30 heteroaryl, C4-C 30 Heteroarylalkyl, C3-C 30 Heteroaryl groups and C3-C 30 The group consisting of heteroaryl amino groups. For example, when R and R 1 To R 3 Each independently constitutes C3-C 30 When heteroaryl, R and R 1 To R 3Each group is independently selected from, but is not limited to, unfused or fused heteroaryl groups, such as pyrroloyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetraazinyl, imidazolyl, pyrazolyl, indoleyl, isoindoleyl, indolizinyl, pyrroloazinyl, carbazoleyl, benzo[carbazoleyl], dibenzo[carbazoleyl], indolecarbazoleyl, indocarbazoleyl, benzofurancarbazoleyl, benzothiocarbazoleyl, carbolinyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, cinnamyl, quinazolinyl, quinolinyl, purinyl, benzoquinolinyl, benzo[isoquinolinyl], benzo[quinoxalinyl], acridineyl, phenazinyl, phenoxazinyl, phenoxazinyl, phen... Thiazinyl, phenanthrolinyl, piperidinyl, phenanthridine, pteridinyl, naphridinyl, furanyl, pyranyl, oxazinyl, oxazolyl, oxadiazolyl, triazolyl, dioxinyl, benzofuranyl, dibenzofuranyl, thiopyranyl, xanthenyl, chromenyl, isochromenyl, thioazinyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, difuran-pyazinyl, benzofuran-dibenzofuranyl, benzothiopheneyl-benzothiopheneyl, benzothiopheneyl-dibenzothiopheneyl, benzothiopheneyl-benzofuranyl, benzothiopheneyl-dibenzofuranyl, xanthenyl-linked spiroacridinyl, bound by at least one C1-C 10 Alkyl-substituted dihydroacrylinyl and N-substituted spirofluorenyl.

[0115] As an example, R and R 1 To R 3 Each of the aromatic or heteroaromatic groups can consist of one to three aromatic or heteroaromatic rings. When R and R 1 To R 3 When the number of aromatic or heteroaromatic rings exceeds three, the conjugated structure of the first compound 232 becomes too long, resulting in a band gap that is too narrow. For example, R and R 1 To R 3 The aryl or heteroaryl groups are each independently selected from, but not limited to, the group consisting of phenyl, biphenyl, naphthyl, anthracene, pyrrolyl, triazinyl, imidazolyl, pyrazolyl, pyridyl, pyridinyl, pyrimidinyl, pyridazinyl, furanyl, benzofuranyl, dibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, carbazolyl, acridinel, carbaolinyl, phenazinyl, phenoxazinyl, and phenothiazinyl.

[0116] Or, two adjacent R 1 , and / or R 2 and R 3 Further unsubstituted or substituted C3-C 30 Alicyclic (e.g., C5-C) 10 Alicyclic, unsubstituted or substituted C3-C 30 heterocyclic rings (e.g., C3-C)10 heterocyclic rings), unsubstituted or substituted C6-C 30 Aroma rings (e.g., C6-C) 20 Aromatic rings or unsubstituted or substituted C3-C 30 heterocyclic aromatic rings (e.g., C3-C) 20 (Heteroaromatic rings). Aliphatic rings, heteroaliphatic rings, aromatic rings, and heteroaromatic rings consist of: two adjacent carbon atoms R 1 ; or R 2 and R 3 The formation is not limited to specific rings. For example, the aromatic or heteroaromatic rings formed by these groups are each independently selected from, but not limited to, unsubstituted or substituted rings with at least one C1-C2 group. 10 Alkyl-substituted benzene rings, pyridine rings, indole rings, pyran rings, and fluorene rings.

[0117] Compound 232 is an organometallic compound having the structure of Formula 1-1. Its ligands are fused with multiple aromatic rings and / or heteroaromatic rings, thus exhibiting a narrow full width at half maximum (FWHM) in its photoluminescence spectrum. In particular, due to its rigid chemical conformation, compound 232 does not undergo rotation during luminescence, thereby maintaining a good luminescence lifetime. Furthermore, because compound 232 exhibits a specific range of photoluminescence, the color purity of the light emitted from compound 232 can be improved.

[0118] Furthermore, the first compound 232 can be a heterocyclic metal complex comprising two distinct bidentate ligands coordinated to the central metal atom (n is a positive integer in Formula 1-1). By combining two different bidentate ligands, the photoluminescence purity and emission color of the first compound 232 can be easily controlled. Moreover, the color purity and emission peak of the first compound 232 can be controlled by introducing various substituents into each ligand. For example, the first compound 232 having the structure of Formula 1-1 can emit yellow to red and can improve the luminous efficiency of organic light-emitting diodes.

[0119] In one exemplary aspect, the first compound 232 may have X represented by formulas 1-2. 3 -X 5 Y 1 And the ring (a) of Ato.

[0120] [Equation 1-2]

[0121]

[0122] Where X 21 To X 27 Each independently for CR 1 Or N; Y 3 It is BR 2 CR 2R 3 C=O, SiR 2 R 3 GeR 2 R 3 PR 2 ,P=O,O,S,SO2,Se,SeO2,Te,TeO2 or NR a ; and M, R, m, n, R 1 To R 3 and R a Same as defined in Equation 1-1.

[0123] In an alternative aspect, the first compound 232 can be represented by formulas 1-3 having X 8 -X 11 Y 2 The ring (b) of B.

[0124] [Equation 1-3]

[0125]

[0126] Where X 31 To X 38 Each is independently CR1 or N; Y 4 It is BR 2 CR 2 R 3 C=O, SiR 2 R 3 GeR 2 R 3 PR 2 ,P=O,O,S,SO2,Se,SeO2,Te,TeO2 or NR a M, m, n, R 1 To R 3 and R a They are the same as the definitions in Equation 1-1.

[0127] For example, M can be iridium (Ir), palladium (Pd), or platinum (Pt). X 31 To X 38 It can be CR 1 R 1 The free choice can be hydrogen, protium, deuterium, and unsubstituted or deuterated C1-C atoms. 20 The group consisting of alkyl groups, or alternatively, X 31 To X 33 R 1 The two in can form unsubstituted or C1-C 20 Alkyl-substituted C6-C 30 Fangzu ring. Y4 It can be CR 2 R 3 N a Or O. R 2 and R 3 Each is independently selected from hydrogen, protium, deuterium, unsubstituted or deuterated C1-C. 20 Alkyl and C6-C 30 A group composed of aromatic groups (aryl groups). Furthermore, one of m and n can be 1, and the other of m and n can be 2.

[0128] More specifically, in Equation 1-2, X 25 and X 26 They are interconnected to form aromatic or heteroaromatic rings, such that the first compound 232 can be represented by formulas 1-4. Alternatively, in formula 1-2, X 26 and X 27 They are connected to each other to form an aromatic ring or a heteroaromatic ring, such that the first compound 232 can be represented by formulas 1-5.

[0129] [Equations 1-4]

[0130]

[0131] [Equations 1-5]

[0132]

[0133] Where X 41 To X 45 Each independently for CR 1 Or N; M, R, m, n and R 1 To R 3 The definitions are the same as those in Equation 1-1; X 21 To X 24 and Y 3 Same as the definition in Equation 1-2;

[0134] Alternatively, in equation 1-3, X 31 and X 32 They are interconnected to form aromatic or heteroaromatic rings, such that the first compound 232 can be represented by formulas 1-6. Alternatively, in formulas 1-3, X 32 and X 33 They are connected to each other to form an aromatic ring or a heteroaromatic ring, such that the first compound 232 can be represented by formulas 1-7.

[0135] [Equations 1-6]

[0136]

[0137] [Equations 1-7]

[0138]

[0139] Where X 51 To X 55 Each independently for CR 1 Or N; M, m, n, R 1 To R 3 Same as the definition in Equation 1-1; X 34 To X 38 Y 4 They are the same as those defined in Equations 1-3.

[0140] For example, M can be iridium (Ir), palladium (Pd), or platinum (Pt). X 31 To X 38 and X 5 To X 55 One of them can be N, and the rest are X 31 To X 38 and X 5 To X 55 It can be CR 1 Y 4 It can be CR 2 R 3 N a 、O or S. R 1 The free choice can be hydrogen, protium, deuterium, unsubstituted or deuterated C1-C. 20 Alkyl, C1-C 20 Alkyl silyl, C6-C 30 Aryl groups (aryl) and C3-C 30 The group composed of heteroaryl groups (heteroaryl groups). R 2 and R 3 Each is independently selected from hydrogen, protium, deuterium, unsubstituted or deuterated C1-C. 20 Alkyl, C3-C 30 Alicyclic group, C3-C 30 heterocyclic group, C6-C 30 Aryl (aryl) or C3-C 30 A group consisting of heteroaryl groups (heteroaryl groups), or alternatively, two adjacent R groups. 1 , and / or R 2 and R 3 It can further form C3-C 30 Alicyclic, C3-C 30 Aliphatic ring, C6-C 30 Aromatic rings or C3-C 30 Mixed fragrance ring.

[0141] For example, in Equation 1-1, the auxiliary ligand It can be a bidentate ligand, where Z 1 and Z 2 The ligand is independently selected from the group consisting of oxygen, nitrogen, and phosphorus atoms. The bidentate ligand can be an acetylacetone ligand, or an N,N'- or N,O- bidentate anion ligand.

[0142] For example, the central coordinating metal could be iridium, and the auxiliary ligands could be... It can be an acetylacetone ligand. That is, the first compound 232 can be represented by one of formulas 1-8 to 1-11:

[0143] [Equations 1-8]

[0144]

[0145] [Equations 1-9]

[0146]

[0147] [Equation 1-10]

[0148]

[0149] [Equation 1-11]

[0150]

[0151] In equations 1-8 and 1-9, R is defined the same as in equation 1-1; X 21 To X 24 X 34 To X 38 X 41 To X 45 and X 51 To X 55 Each independently for CR 1 Or N; Y 3 and Y 4 Each independently as BR 2 CR 2 R 3 C=O, SiR 2 R 3 GeR 2 R 3 PR 2 P = O, O, S, SO2, Se, SeO2, Te or TeO2 or NR a ;R 1 To R 3 and R a They are the same as those defined in Equation 1-1; R 11 To R 13Each is independently selected from hydrogen, tritium, deuterium, tritium, halogen atom, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, unsubstituted or substituted C1-C. 20 Alkyl, unsubstituted or substituted C2-C 20 Alkenyl, unsubstituted or substituted C2-C 20 Alkyne group, unsubstituted or substituted C1-C 20 Alkoxy, amino, unsubstituted or substituted C1-C 20 Alkylamino, unsubstituted or substituted C1-C 20 Alkyl silyl, carboxyl, nitrile, isonitrile, thioalkyl, phosphine, unsubstituted or substituted C3-C 30 Alicyclic group, unsubstituted or substituted C3-C 30 Heterocyclic groups, unsubstituted or substituted C6-C 30 Aromatic groups and unsubstituted or substituted C3-C 30 A group consisting of heteroaryrophores; m is an integer from 1 to 3; n is an integer from 0 to 2; where m+n is 3.

[0152] In Equation 1-1, M can be iridium, and Z... 1 and Z 2 One of them could be an oxygen atom, Z 1 and Z 2 The other atom in the formula can be a nitrogen atom. That is, the first compound 232 can be represented by one of formulas 1-12 to 1-15.

[0153] [Equation 1-12]

[0154]

[0155] [Equation 1-13]

[0156]

[0157] [Equation 1-14]

[0158]

[0159] [Equation 1-15]

[0160]

[0161] In equations 1-12 and 1-13, R is defined the same as in equation 1-1; X 21 To X 24 X 34 To X 38 X 41 To X 45 and X 51 To X 55 Each independently for CR 1Or N; Y 3 and Y 4 Each independently as BR 2 CR 2 R 3 C=O, SiR 2 R 3 GeR 2 R 3 PR 2 P = O, O, S, SO2, Se, SeO2, Te or TeO2 or NR a ;R 1 To R 3 and R a They are the same as those defined in Equation 1-1; R 61 To R 64 Each is independently selected from hydrogen, protium, deuterium, tritium, halogen atom, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, unsubstituted or substituted C1-C. 20 Alkyl, unsubstituted or substituted C2-C 20 Alkenyl, unsubstituted or substituted C2-C 20 Alkyne group, unsubstituted or substituted C1-C 20 Alkoxy, amino, unsubstituted or substituted C1-C 20 Alkylamino, unsubstituted or substituted C1-C 20 Alkyl silyl, carboxyl, nitrile, isonitrile, thioalkyl, phosphine, unsubstituted or substituted C3-C 30 Alicyclic group, unsubstituted or substituted C3-C 30 Heterocyclic groups, unsubstituted or substituted C6-C 30 Aromatic groups and unsubstituted or substituted C3-C 30 A group consisting of heteroaryrophores; m is an integer from 1 to 3; n is an integer from 0 to 2; where m+n is 3.

[0162] In Equation 1-1, M can be iridium, and Z... 1 and Z 2 It can be a nitrogen atom. That is, the first compound 232 can be represented by one of formulas 1-16 to 1-23.

[0163] [Equation 1-16]

[0164]

[0165] [Equation 1-17]

[0166]

[0167] [Equation 1-18]

[0168]

[0169] [Equation 1-19]

[0170]

[0171] [Equation 1-20]

[0172]

[0173] [Equation 1-21]

[0174]

[0175] [Equation 1-22]

[0176]

[0177] [Equation 1-23]

[0178]

[0179] In equations 1-16, 1-17, 1-20, and 1-21, R is defined the same as in equation 1-1; X 21 To X 24 X 34 To X 38 X 41 To X 45 and X 51 To X 55 Each independently for CR 1 Or N; Y 3 and Y 4 Each independently as BR 2 CR 2 R 3 C=O, SiR 2 R 3 GeR 2 R 3 PR2, P=O, O, S, SO2, Se, SeO2, Te or TeO2 or NR a ;R 1 To R 3 and R a They are the same as those defined in Equation 1-1; m is an integer from 1 to 3, n is an integer from 0 to 2, where m+n is 3; R in Equations 1-16 to 1-19 71 To R 73 Each is independently selected from hydrogen, protium, deuterium, tritium, halogen atom, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, unsubstituted or substituted C1-C. 20 Alkyl, unsubstituted or substituted C2-C 20 Alkenyl, unsubstituted or substituted C2-C 20Alkyne group, unsubstituted or substituted C1-C 20 Alkoxy, amino, unsubstituted or substituted C1-C 20 Alkylamino, unsubstituted or substituted C1-C 20 Alkyl silyl, carboxyl, nitrile, isonitrile, thioalkyl, phosphine, unsubstituted or substituted C3-C 30 Alicyclic group, unsubstituted or substituted C3-C 30 Heterocyclic groups, unsubstituted or substituted C6-C 30 Aromatic groups and unsubstituted and substituted C3-C 30 Groups composed of heteroaryl groups; R in formulas 1-20 to 1-23 81 To R 85 Each is independently selected from hydrogen, protium, deuterium, tritium, halogen atom, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, unsubstituted or substituted C1-C. 20 Alkyl, unsubstituted or substituted C2-C 20 Alkenyl, unsubstituted or substituted C2-C 20 Alkyne group, unsubstituted or substituted C1-C 20 Alkoxy, amino, unsubstituted or substituted C1-C 20 Alkylamino, unsubstituted or substituted C1-C 20 Alkyl silyl, carboxyl, nitrile, isonitrile, thioalkyl, phosphine, unsubstituted or substituted C3-C 30 Alicyclic group, unsubstituted or substituted C3-C 30 Heterocyclic groups, unsubstituted or substituted C6-C 30 Aromatic groups and unsubstituted or substituted C3-C 30 A group composed of aromatic compounds.

[0180] For example, the first compound 232 represented by formula 1-8 can be one of the compounds in formula 1-24.

[0181] [Equation 1-24]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199] For example, the first compound 232 represented by formula 1-9 can be one of the compounds in formula 1-25.

[0200] [Equation 1-25]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219] For example, the first compound 232 represented by formula 1-10 can be one of the compounds in formula 1-26.

[0220] [Equation 1-26]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233] When Y in equation 1-11 4 It is an unsubstituted or substituted carbon atom, i.e., CH2 or CR. 2 R 3 In this case, the first compound 232 can be one of the compounds in formulas 1-27.

[0234] [Equation 1-27]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243] When Y in equation 1-11 4 It is an unsubstituted or substituted heteroatom, i.e., NR a When O, the first compound 232 can be one of the compounds in formulas 1-28.

[0244] [Equation 1-28]

[0245]

[0246]

[0247]

[0248]

[0249] For example, the first compound 232 can be one of the compounds in formulas 1-29.

[0250] [Equation 1-29]

[0251]

[0252]

[0253] Synthesis Example 1: Synthesis of Compound 369 (Compound RD7 in Formula 8) (1) Synthesis of compound B-1

[0254] [Reaction Formula 1-1]

[0255]

[0256] Compound A-1 (5-bromoquinoline, 50.0 g, 240.33 mmol), propane-2-boronic acid (42.25 g, 480.65 mmol), Pd2(dba)3 (tris(dibenzylacetone)dipalladium(0), 6.6 g, 3 mol%), SPhos (2-bicyclohexylphosphine-2',6'-dimethoxydiphenyl, 9.9 g, 24.03 mmol), potassium phosphate monohydrate (276.71 g, 1.2 mol), and toluene (1000 mL) were added to a reaction vessel, and the solution was stirred at 120 °C for 12 hours. After the reaction was complete, the solution was cooled to room temperature and extracted with ethyl acetate to remove the solvent. The crude product was purified by column chromatography (elution: ethyl acetate and hexane) to give compound B-1 (5-isopropylquinoline, 35.4 g, yield: 86%).

[0257] MS (m / z): 171.10

[0258] (2) Synthesis of compound C-1

[0259] [Reaction 1-2]

[0260]

[0261] Compound B-1 (5-isopropylquinoline, 35.4 g, 206.73 mmol), mCBPA (3-chloroperbenzoic acid, 53.5 g, 310.09 mmol), and dichloromethane (500 mL) were added to a reaction vessel, and the solution was stirred at room temperature for 3 hours. Sodium sulfite (80 g) was added to the solution, the organic layer was washed with water, and then the solution was subjected to reduced pressure to give compound C-1 (27.5 g, yield: 71%).

[0262] MS (m / z): 187.10

[0263] (3) Synthesis of compound D1

[0264] [Reaction Formula 1-3]

[0265]

[0266] Compound C-1 (27.5 g, 146.87 mmol) dissolved in toluene (500 mL) was placed in a reaction vessel, and phosphorus oxychloride (POCl3, 45.0 g, 293.74 mmol) and diisopropylethylamine (DIPEA, 38.0 g, 293.74 mmol) were added. The solution was then stirred at 120 °C for 4 hours. The solvent was removed from the reactants under reduced pressure, and the mixture was extracted with dichloromethane and washed with an organic layer of water. Water was removed with MgSO4, and the crude product was filtered off, followed by solvent removal. The crude product was purified by column chromatography to give compound D-1 (2-chloro-5-isopropylquinoline, 11.8 g, yield: 39%).

[0267] MS (m / z): 205.07

[0268] (4) Synthesis of compound F-1

[0269] [Reaction Equations 1-4]

[0270]

[0271] Compound E-1 (1-naphthoic acid, 50 g, 290.30 mmol) and SOCl2 (200 mL) were added to a reaction vessel. The solution was refluxed for 4 hours to remove SOCl2. Ethanol (200 mL) was added, and the solution was stirred at 70 °C for 7 hours. Water was added, and the organic layer was extracted with diethyl ether. The water was removed with MgSO4, and the solution was filtered. The solvent was removed under reduced pressure to give compound F-1 (ethyl 1-naphthoic acid, 53.2 g, 90% yield).

[0272] MS (m / z): 200.08

[0273] (5) Synthesis of compound G-1

[0274] [Reaction Formulas 1-5]

[0275]

[0276] Compound F-1 (ethyl 1-naphthylcarboxylate, 52.3 g, 261.20 mmol), NBS (N-bromosuccinimide, 51.14 g, 287.32 mmol), Pd(OAc)2 (palladium(II) acetate, 0.6 g, 2.61 mmol), Na2S2O8 (124.4 g, 522.40 mmol), and dichloromethane (500 mL) were added to a reaction vessel, along with TfOH (trifluoromethanesulfonic acid, 19.6 g, 130.60 mmol). The solution was then stirred at 70 °C for 1 hour. The reactants were cooled to room temperature, and the reaction was completed using NaHCO3, followed by extraction with dichloromethane. The water in the organic layer was removed with MgSO4, the solvent was removed, and the crude product was purified by column chromatography (eluent: petroleum ether and ethyl acetate) to give compound G-1 (ethyl 8-bromonaphthyl-1-carboxylate, 54.0 g, yield: 74%).

[0277] MS (m / z): 277.99

[0278] (6) Synthesis of compound H-1

[0279] [Reaction Equations 1-6]

[0280]

[0281] Compound G-1 (ethyl 8-bromonaphthyl-1-carboxylate, 54.0 g, 193.46 mmol), bis(pinacol)diboron (58.6 g, 232.15 mmol), Pd(dppf)Cl2 ([1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloride, 7.1 g, 9.67 mmol), KOAc (potassium acetate, 57.0 g, 580.37 mmol), and 1,4-dioxane (500 mL) were added to a reaction vessel, and the solution was stirred at 100 °C for 4 hours. The reaction mixture was cooled to room temperature, extracted with ethyl acetate, and the water in the organic layer was removed with MgSO4. The solution was then filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (elution: hexane and ethyl acetate) to give compound H-1 (ethyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)naphthalene-1-carboxylate, 54.3 g, yield: 86%).

[0282] MS (m / z): 326.17

[0283] (7) Synthesis of compound I-1

[0284] [Reaction Equations 1-7]

[0285]

[0286] Compound D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol), compound H-1 (ethyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)naphthalene-1-carboxylate, 17.45 g, 53.48 mmol), Pd(OAc)2 (0.5 g, 2.43 mmol), PPh3 (chloro(triphenylphosphine)[2-(2'-amino-1,1'-biphenyl)]palladium(II), 2.6 g, 9.72 mmol), K2CO3 (20.2 g, 145.86 mmol), 1,4-dioxane (100 mL), and water (100 mL) were added to a reaction vessel, and the solution was stirred at 100 °C for 12 hours. The reaction mixture was cooled to room temperature and extracted with ethyl acetate. The water in the organic layer was removed with MgSO4, and the solution was then filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (eluent: hexane and ethyl acetate) to give compound I-1 (ethyl 8-(5-isopropylquinolin-2-yl)naphthalene-1-carboxylate, 13.5 g, yield: 75%). MS (m / z): 369.17

[0287] (8) Synthesis of compound J-1

[0288] [Reaction Equations 1-8]

[0289]

[0290] Compound I-1 (ethyl 8-(5-isopropylquinoline-2-yl)naphth-1-carboxylate, 13.5 g, 36.6 mmol) and THF (100 mL) were added to the reaction vessel, followed by the dropwise addition of CH3MgBr (21.8 g, 182.70 mmol) at 0 °C. The solution was brought to room temperature, and the reaction was completed after 12 hours. The mixture was extracted with ethyl acetate, and the water in the organic layer was removed with MgSO4. The solution was then filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (eluent: hexane and ethyl acetate) to give compound J-1 (2-(1-(5-isopropylquinoline-2-yl)naphth-8-yl)prop-2-ol, 6.9 g, yield: 53%).

[0291] MS (m / z): 355.19

[0292] (9) Synthesis of compound K-1

[0293] [Reaction formulas 1-9]

[0294]

[0295] Compound J-1 (2-(1-(5-isopropylquinolin-2-yl)naphth-8-yl)prop-2-ol, 20 g, 56.26 mmol) and a mixed aqueous solution of acetic acid and sulfuric acid (200 mL) were added to a reaction vessel, and the solution was refluxed for 16 hours. After the reaction was complete, the solution was cooled to room temperature, and the reactants were added dropwise to an ice-cold aqueous solution of sodium hydroxide. The organic layer was extracted with dichloromethane and water was removed with MgSO4. After removing the solvent, the crude product was recrystallized from toluene and ethanol to give a yellow solid of compound K-1 (9-isopropyl-7,7-dimethyl-7H-naphtho[1,8-bc]acridine, 10.25 g, yield: 54%).

[0296] MS (m / z): 337.18

[0297] (10) Synthesis of compound L-1

[0298] [Reaction Formula 1-10]

[0299]

[0300] Compound K-1 (10.25 g, 30.37 mmol), 2-ethoxyethanol (200 mL), and distilled water (50 mL) were added to a reaction vessel. Nitrogen gas was bubbled through the solution for 1 hour, followed by the addition of IrCl3·H2O (4.4 g, 13.81 mmol). The solution was then refluxed for 2 days. After the reaction was complete, the solution was cooled to room temperature and filtered to obtain a solid. The solid was washed with hexane and water and dried to give compound L-1 (4.0 g, yield: 32%).

[0301] (11) Synthesis of compound 369

[0302] [Reaction Formula 1-11]

[0303]

[0304] Compound L-1 (4.0 g, 2.21 mmol), 3,7-diethylnonane-4,6-dione (4.7 g, 22.09 mmol), Na₂CO₃ (4.7 g, 441.8 mmol), and 2-ethoxyethanol (100 mL) were added to a reaction vessel, and the solution was slowly stirred for 24 hours. After the reaction was complete, dichloromethane was added to the reactants to dissolve the product, and the solution was filtered through diatomaceous earth. The solvent was removed, the solid was filtered through filter paper, and the filtered solid was then placed in isopropanol, and the solution was stirred. The solution was filtered to remove the isopropanol, dried, and recrystallized from dichloromethane and isopropanol. The solution was purified using a sublimation apparatus to obtain compound 369 (2.5 g, yield: 53%) with high purity.

[0305] MS (m / z): 1076.48

[0306] Synthesis Example 2: Synthesis of Compound 2 (Compound RD5 in Formula 8)

[0307] (1) Synthesis of compound C-2

[0308] [Reaction 2-1]

[0309]

[0310] The synthesis of compound I-1 was repeated to obtain compound C-2 (ethyl 3-6-(isopropylisoquinoline-1-yl)-naphthoate, 14.4 g, yield: 80%), except that compounds A-2 (1-chloro-6-isopropylisoquinoline, 10 g, 48.62 mmol) and B-2 (ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxoborhecyclopentan-2-yl)-2-naphthoate (17.45 g, 53.50 mmol) were used instead of compounds D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and H-1 (ethyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxoborhecyclopentan-2-yl)naphthalene-1-carboxylate).

[0311] MS (m / z): 369.17

[0312] (2) Synthesis of compound D-2

[0313] [Reaction 2-2]

[0314]

[0315] The synthesis of compound J-1 was repeated to obtain compound D-2 (2-(3-(6-isopropylisoquinoline-1-yl)naphth-2-yl)prop-2-ol, 6.9 g, yield: 50%), except that compound C-2 (ethyl 3-(6-isopropylisoquinoline-1-yl)-2-naphthylcarboxylate, 14.4 g, 39.0 mmol) was used instead of compound I-1 (ethyl 8-(5-isopropylquinoline-2-yl)naphth-1-carboxylate, 13.5 g, 36.5 mmol).

[0316] MS (m / z): 355.19

[0317] (3) Synthesis of compound E-2

[0318] [Reaction 2-3]

[0319]

[0320] The synthesis of compound K-1 was repeated to obtain compound E-2 (5-isopropyl-7,7-dimethyl-7H-benzo[de]naphtha[2,3-h]quinolone, 11.39 g, yield: 60%), except that compound D-2 (2-(3-(6-isopropylisoquinoline-1-yl)naphth-2-yl)prop-2-ol, 20 g, 56.26 mmol) was used instead of compound J-1 (2-(1-(5-isopropylquinoline-2-yl)naphth-8-yl)prop-2-ol, 20 g, 56.26 mmol). MS (m / z): 337.18

[0321] (4) Synthesis of compound F-2

[0322] [Reaction 2-4]

[0323]

[0324] The synthesis of compound L-1 was repeated to obtain compound F-2 (4.7 g, yield: 34%), except that compound E-2 (11.39 g, 33.76 mmol) was used instead of compound K-1 (10.25 g, 30.37 mmol).

[0325] (5) Synthesis of Compound 2

[0326] [Reaction 2-5]

[0327]

[0328] The synthesis of compound 369 was repeated to obtain compound 2 (3.2 g, yield: 57%), except that compound F-2 (4.7 g, 2.61 mmol) was used instead of compound L-1 (4.0 g, 2.21 mmol).

[0329] MS (m / z): 1076.48

[0330] Synthesis Example 3: Synthesis of Compound 501 (Compound RD8 in Formula 8) become

[0331] (1) Synthesis of compound C-3

[0332] [Reaction 3-1]

[0333]

[0334] The synthesis of compound I-1 was repeated to obtain compound C-3 (ethyl 8-6-(isopropylisoquinoline-3-yl)-naphthoate, 12.6 g, yield: 70%), except that compound A-3 (3-chloro-6-isopropylisoquinoline, 10 g, 48.62 mmol) was used instead of compound D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol).

[0335] MS (m / z): 369.17

[0336] (2) Synthesis of compound D-3

[0337] [Reaction 3-2]

[0338]

[0339] The synthesis of compound J-1 was repeated to obtain compound D-3 (2-(8-(6-isopropylisoquinoline-3-yl)naphth-1-yl)prop-2-ol, 7.3 g, yield: 60%), except that compound C-3 (ethyl 8-(6-isopropylisoquinoline-3-yl)naphthylcarboxylate, 12.6 g, 34.0 mmol) was used instead of compound I-1 (ethyl 8-(5-isopropylquinoline-2-yl)naphth-1-carboxylate, 13.5 g, 36.5 mmol).

[0340] MS (m / z): 355.19

[0341] (3) Synthesis of compound E-3

[0342] [Reaction 3-3]

[0343]

[0344] The synthesis of compound K-1 was repeated to obtain compound E-3 (2-isopropyl-13,13-dimethyl-13H-naphtho[1,8-bc]phenanthridine, 4.3 g, yield: 62%), except that compound D-3 (2-(8-(6-isopropylisoquinoline-3-yl)naphth-1-yl)prop-2-ol, 7.3 g, 20.4 mmol) was used instead of compound J-1 (2-(1-(5-isopropylquinoline-2-yl)naphth-8-yl)prop-2-ol, 20 g, 56.26 mmol).

[0345] Mass spectrometry (m / z): 337.18

[0346] (4) Synthesis of compound F-3

[0347] [Reaction 3-4]

[0348]

[0349] The synthesis of compound L-1 was repeated to obtain compound F-3 (1.9 g, yield: 37%), except that compound E-3 (2-isopropyl-13,13-dimethyl-13H-naphtho[1,8-bc]phenanthridine, 4.3 g, 12.6 mmol) was used instead of compound K-1 (10.25 g, 30.37 mmol).

[0350] (5) Synthesis of compound 501

[0351] [Reaction 3-5]

[0352]

[0353] The synthesis of compound 369 was repeated to obtain compound 501 (1.4 g, yield: 60%), except that compound F-3 (1.9 g, 1.07 mmol) was used instead of compound L-1 (4.0 g, 2.21 mmol).

[0354] MS (m / z): 1076.48

[0355] Synthesis Example 4: Synthesis of Compound 182 (Compound RD6 in Formula 8)

[0356] (1) Synthesis of compound C-4

[0357] [Reaction 4-1]

[0358]

[0359] The synthesis of compound I-1 was repeated to obtain compound C-4 (12.2 g, yield: 68%), except that compounds A-4 (10 g, 48.62 mmol) and B-4 (17.45 g, 53.48 mmol) were used instead of compounds D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)naphthalene-1-carboxylic acid ethyl ester (17.45 g, 53.48 mmol) respectively.

[0360] MS (m / z): 369.17

[0361] (2) Synthesis of compound D-4

[0362] [Reaction 4-2]

[0363]

[0364] The synthesis of compound J-1 was repeated to obtain compound D-4 (6.8 g, yield: 58%), except that compound C-4 (12.2 g, 33.02 mmol) was used instead of compound I-1 (ethyl 8-(5-isopropylquinolin-2-yl)naphthalene-1-carboxylate, 13.5 g, 36.5 mmol).

[0365] MS (m / z): 355.19

[0366] (3) Synthesis of compound E-4

[0367] [Reaction 4-3]

[0368]

[0369] The synthesis of compound K-1 was repeated to obtain compound E-4 (4.1 g, yield: 63%), except that compound D-4 (6.8 g, 19.15 mmol) was used instead of compound J-1 (2-(1-(5-isopropylquinolin-2-yl)naphth-8-yl)prop-2-ol, 20 g, 56.26 mmol).

[0370] MS (m / z): 337.18

[0371] (4) Synthesis of compound F-4

[0372] [Reaction 4-4]

[0373]

[0374] The synthesis of compound L-1 was repeated to obtain compound F-4 (2.1 g, yield: 42%), except that compound E-4 (4.1 g, 12.15 mmol) was used instead of compound K-1 (10.25 g, 30.37 mmol).

[0375] (5) Synthesis of compound 182

[0376] [Reaction 4-5]

[0377]

[0378] The synthesis of compound 369 was repeated to obtain compound 182 (1.1 g, yield: 57%), except that compound F-4 (2.1 g, 1.17 mmol) was used instead of compound L-1 (4.0 g, 2.21 mmol).

[0379] MS (m / z): 1076.48

[0380] Synthesis Example 5: Synthesis of Compound 154 (Compound RD9 in Formula 8)

[0381] (1) Synthesis of compound C-5

[0382] [Reaction 5-1]

[0383]

[0384] The synthesis of compound I-1 was repeated to obtain compound C-5 (11.8 g, yield: 78%), except that compounds A-5 (10 g, 48.62 mmol) and B-5 (14.4 g, 53.48 mmol) were used instead of compounds D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)naphthalene-1-carboxylic acid ethyl ester (17.45 g, 53.48 mmol)).

[0385] MS (m / z): 312.16

[0386] (2) Synthesis of compound D-5

[0387] [Reaction 5-2]

[0388]

[0389] Compound C-5 (11.8 g, 37.75 mmol) and dimethyl sulfoxide (DMSO) (200 mL) were added to a reaction vessel, followed by CuI (10.8 g, 56.66 mmol). The solution was then refluxed at 150 °C for 12 hours. After the reaction was complete, the solution was filtered, extracted with ethyl acetate, and the water in the organic layer was removed with MgSO4. The solution was then filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (eluent: hexane and ethyl acetate) to give compound D-5 (4.6 g, yield: 39%).

[0390] MS (m / z): 310.15

[0391] (3) Synthesis of compound E-5

[0392] [Reaction 5-3]

[0393]

[0394] Compound D-5 (4.6 g, 14.82 mmol), 1-iodobenzene (3.3 g, 16.30 mmol), and toluene (200 mL) were added to a reaction vessel. Pd2(dba)3 (0.7 g, 0.74 mmol), P(t-Bu)3 (tri-tert-butylphosphine, 0.3 g, 1.48 mmol), and NaOt-Bu (sodium tert-butoxide, 2.8 g, 29.64 mmol) were then added to the reaction vessel, and the solution was refluxed at 100 °C for 24 hours. After the reaction was complete, the solution was extracted with ethyl acetate, and the water in the organic layer was removed with MgSO4. The solution was then filtered and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (eluent: hexane and ethyl acetate) to give compound E-5 (4.6 g, yield: 81%).

[0395] MS (m / z): 386.18

[0396] (4) Synthesis of compound F-5

[0397] [Reaction 5-4]

[0398]

[0399] The synthesis of compound L-1 was repeated to obtain compound F-5 (2.5 g, yield: 47%), except that compound E-5 (4.6 g, 11.90 mmol) was used instead of compound K-1 (10.25 g, 30.37 mmol).

[0400] (5) Synthesis of compound 154

[0401] [Reaction 5-5]

[0402]

[0403] The synthesis of compound 369 was repeated to obtain compound 154 (1.4 g, yield: 46%), except that compound F-5 (2.5 g, 1.25 mmol) was used instead of compound L-1 (4.0 g, 2.21 mmol).

[0404] MS (m / z): 1174.47

[0405] Synthesis Example 6: Synthesis of Compound 334 (Compound RD10 in Formula 8)

[0406] (1) Synthesis of compound C-6

[0407] [Reaction 6-1]

[0408]

[0409] The synthesis of compound I-1 was repeated to obtain compound C-6 (11.4 g, yield: 75%), except that compounds A-6 (10 g, 48.62 mmol) and B-6 (14.4 g, 53.48 mmol) were used instead of compound D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and compound H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)naphthalene-1-carboxylic acid ethyl ester (17.45 g, 53.48 mmol)).

[0410] MS (m / z): 312.16

[0411] (2) Synthesis of compound D-6

[0412] [Reaction 6-2]

[0413]

[0414] The synthesis of compound D5 was repeated to obtain compound D-6 (6.8 g, yield: 58%), except that compound C-6 (11.4 g, 35.49 mmol) was used instead of compound C-5 (11.8 g, 37.77 mmol).

[0415] MS (m / z): 310.15

[0416] (3) Synthesis of compound E-6

[0417] [Reaction 6-3]

[0418]

[0419] The synthesis of compound E-5 was repeated to obtain compound E-6 (5.6 g, yield: 78%), except that compound D-6 (5.8 g, 18.61 mmol) was used instead of compound D-5 (4.6 g, 14.82 mmol).

[0420] MS (m / z): 386.18

[0421] (4) Synthesis of compound F-6

[0422] [Reaction 6-4]

[0423]

[0424] The synthesis of compound L-1 was repeated to obtain compound F-6 (2.8 g, yield: 42%), except that compound E-6 (5.6 g, 14.49 mmol) was used instead of compound K-1 (10.25 g, 30.37 mmol).

[0425] (5) Synthesis of compound 334

[0426] [Reaction 6-5]

[0427]

[0428] The synthesis of compound 369 was repeated to obtain compound 334 (2.0 g, yield: 61%), except that compound F-6 (2.8 g, 1.38 mmol) was used instead of compound L-1 (4.0 g, 2.21 mmol).

[0429] MS (m / z): 1174.47

[0430] Synthesis Example 7: Synthesis of Compound 465 (Compound RD11 in Formula 8)

[0431] (1) Synthesis of compound C-7

[0432] [Reaction Formula 7-1]

[0433]

[0434] The synthesis of compound I-1 was repeated to obtain compound C-7 (9.0 g, yield: 50%), except that compounds A-7 (10 g, 48.62 mmol) and B-7 (14.4 g, 53.48 mmol) were used instead of compounds D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)naphthalene-1-carboxylic acid ethyl ester (17.45 g, 53.48 mmol) respectively.

[0435] MS (m / z): 312.16

[0436] (2) Synthesis of compound D-7

[0437] [Reaction 7-2]

[0438]

[0439] The synthesis of compound D-5 was repeated to obtain compound D-7 (7.4 g, yield: 55%), except that compound C-7 (9.0 g, 28.69 mmol) was used instead of compound C-5 (11.8 g, 37.77 mmol).

[0440] MS (m / z): 310.15

[0441] (3) Synthesis of compound E-7

[0442] [Reaction 7-3]

[0443]

[0444] The synthesis of compound E-5 was repeated to obtain compound E-7 (4.7 g, yield: 77%), except that compound D-7 (4.9 g, 15.78 mmol) was used instead of compound D-5 (4.6 g, 14.82 mmol). MS (m / z): 386.18

[0445] (4) Synthesis of compound F-7

[0446] [Reaction 7-4]

[0447]

[0448] The synthesis of compound L-1 was repeated to obtain compound F-7 (2.6 g, yield: 48%), except that compound E-7 (4.7 g, 12.16 mmol) was used instead of compound K-1 (10.25 g, 30.37 mmol).

[0449] (5) Synthesis of compound 465

[0450] [Reaction 7-5]

[0451]

[0452] The synthesis of compound 369 was repeated to obtain compound 465 (2.0 g, yield: 64%), except that compound F-7 (2.6 g, 1.33 mmol) was used instead of compound L-1 (4.0 g, 2.21 mmol).

[0453] MS (m / z): 1174.47

[0454] Synthesis Example 8: Synthesis of Compound 582 (Compound RD12 in Formula 8)

[0455] (1) Synthesis of compound C-8

[0456] [Reaction Equation 8-1]

[0457]

[0458] The synthesis of compound I-1 was repeated to obtain compound C-8 (9.0 g, yield: 50%), except that compounds A-8 (10 g, 48.62 mmol) and B-8 (14.4 g, 53.48 mmol) were used instead of compounds D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)naphthalene-1-carboxylic acid ethyl ester (17.45 g, 53.48 mmol)).

[0459] MS (m / z): 312.16

[0460] (2) Synthesis of compound D-8

[0461] [Reaction Equation 8-2]

[0462]

[0463] The synthesis of compound D-5 was repeated to obtain compound D-8 (7.4 g, yield: 55%), except that compound C-8 (10.0 g, 35.01 mmol) was used instead of compound C-5 (11.8 g, 37.77 mmol).

[0464] MS (m / z): 310.15

[0465] (3) Synthesis of compound E-8

[0466] [Reaction Equation 8-3]

[0467]

[0468] The synthesis of compound E-5 was repeated to obtain compound E-8 (5.3 g, yield: 83%), except that compound D-8 (5.1 g, 15.45 mmol) was used instead of compound D-5 (4.6 g, 14.82 mmol). MS (m / z): 386.18

[0469] (4) Synthesis of compound F-8

[0470] [Reaction Equation 8-4]

[0471]

[0472] The synthesis of compound L-1 was repeated to obtain compound F-8 (2.4 g, yield: 39%), except that compound E-8 (5.3 g, 13.66 mmol) was used instead of compound K-1 (10.25 g, 30.37 mmol).

[0473] (5) Synthesis of compound 582

[0474] [Reaction 8-5]

[0475]

[0476] The synthesis of compound 369 was repeated to obtain compound 582 (1.8 g, yield: 64%), except that compound F-8 (2.4 g, 1.1 mmol) was used instead of compound L-1 (4.0 g, 2.21 mmol).

[0477] MS (m / z): 1174.47

[0478] Synthesis Example 9: Synthesis of Compound 168 (Compound RD13 in Formula 8)

[0479] (1) Synthesis of compound C-9

[0480] [Reaction 9-1]

[0481]

[0482] The synthesis of compound I-1 was repeated to obtain compound C-9 (9.9 g, yield: 67%), except that compounds A-9 (10 g, 44.71 mmol) and B-9 (13.3 g, 49.18 mmol) were used instead of compounds D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)naphthalene-1-carboxylic acid ethyl ester (17.45 g, 53.48 mmol) respectively.

[0483] MS (m / z): 331.14

[0484] (2) Synthesis of compound D-9

[0485] [Reaction 9-2]

[0486]

[0487] Compound C-9 (9.9 g, 29.88 mmol) and DMF (100 mL) were added to a reaction vessel, allowing C-9 to dissolve in the DMF. K₂CO₃ (12.4 g, 89.62 mmol) was then added to the reaction vessel, and the solution was stirred at 100 °C for 1 hour. After the reaction was complete, the solution was cooled to room temperature, and then ethanol (100 mL) was added to the reaction vessel. After vacuum distillation of the mixture, the reactants were recrystallized from chloroform / ethyl acetate to give compound D-9 (4.9 g, yield: 53%).

[0488] MS (m / z): 311.13

[0489] (3) Synthesis of compound E-9

[0490] [Reaction 9-3]

[0491]

[0492] The synthesis of compound L-1 was repeated with compound E-9 (3.1 g, yield: 50%), except that compound D-9 (4.9 g, 15.83 mmol) was used instead of compound K-1 (10.25 g, 30.37 mmol).

[0493] (4) Synthesis of compound 168

[0494] [Reaction 9-4]

[0495]

[0496] The synthesis of compound 369 was repeated to obtain compound 168 (2.0 g, yield: 54%), except that compound E-9 (3.1 g, 1.80 mmol) was used instead of compound L-1 (4.0 g, 2.21 mmol).

[0497] MS (m / z): 1024.38

[0498] Synthesis Example 10: Synthesis of Compound 348 (Compound RD14 in Formula 8)

[0499] (1) Synthesis of compound C-10

[0500] [Reaction Formula 10-1]

[0501]

[0502] The synthesis of compound I-1 was repeated to obtain compound C-10 (9.0 g, yield: 64%), except that compounds A-10 (10 g, 44.71 mmol) and B-10 (13.3 g, 49.18 mmol) were used instead of compounds D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and H-1 (ethyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)naphthalene-1-carboxylate, respectively).

[0503] MS (m / z): 331.14

[0504] (2) Synthesis of compound D-10

[0505] [Reaction formula 10-2]

[0506]

[0507] The synthesis of compound D-9 was repeated to obtain compound D-10 (5.0 g, yield: 55%), except that compound C-10 (9.6 g, 29.06 mmol) was used instead of compound C-9 (9.9 g, 28.88 mmol).

[0508] MS (m / z): 311.13

[0509] (3) Synthesis of compound E-10

[0510] [Reaction formula 10-3]

[0511]

[0512] The synthesis of compound L-1 was repeated to obtain compound E-10 (3.5 g, yield: 57%), except that compound D-10 (5.0 g, 15.98 mmol) was used instead of compound K-1 (10.25 g, 30.37 mmol).

[0513] (4) Synthesis of compound 348

[0514] [Reaction formula 10-4]

[0515]

[0516] The synthesis of compound 369 was repeated to obtain compound 348 (1.8 g, yield: 43%), except that compound E-10 (3.5 g, 2.07 mmol) was used instead of compound L-1 (4.0 g, 2.21 mmol).

[0517] MS (m / z): 1024.38

[0518] Synthesis Example 11: Synthesis of Compound 483 (Compound RD15 in Formula 8)

[0519] (1) Synthesis of compound C-11

[0520] [Reaction Formula 11-1]

[0521]

[0522] The synthesis of compound I-1 was repeated to obtain compound C-11 (7.9 g, yield: 53%), except that compounds A-11 (10 g, 44.71 mmol) and B-11 (13.3 g, 49.18 mmol) were used instead of compounds D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)naphthalene-1-carboxylic acid ethyl ester (17.45 g, 53.48 mmol).

[0523] MS (m / z): 331.14

[0524] (2) Synthesis of compound D-11

[0525] [Reaction 11-2]

[0526]

[0527] The synthesis of compound D-9 was repeated to obtain compound D-11 (3.8 g, yield: 51%), except that compound C-11 (7.9 g, 23.07 mmol) was used instead of compound C-9 (9.9 g, 28.88 mmol).

[0528] MS (m / z): 311.13

[0529] (3) Synthesis of compound E-11

[0530] [Reaction 11-3]

[0531]

[0532] The synthesis of compound L-1 was repeated to obtain compound E-11 (3.0 g, yield: 63%), except that compound D-11 (3.8 g, 12.20 mmol) was used instead of compound K-1 (10.25 g, 30.37 mmol).

[0533] (4) Synthesis of compound 483

[0534] [Reaction 11-4]

[0535]

[0536] The synthesis of compound 369 was repeated to obtain compound 483 (1.6 g, yield: 44%), except that compound E-11 (3.0 g, 1.75 mmol) was used instead of compound L-1 (4.0 g, 2.21 mmol).

[0537] MS (m / z): 1024.38

[0538] Synthesis Example 12: Synthesis of Compound 598 (Compound RD16 in Formula 8)

[0539] (1) Synthesis of compound C-12

[0540] [Reaction 12-1]

[0541]

[0542] The synthesis of compound I-1 was repeated to obtain compound C-12 (9.8 g, yield: 66%), except that compounds A-12 (10 g, 44.71 mmol) and B-12 (13.3 g, 49.18 mmol) were used instead of compounds D-1 (2-chloro-5-isopropylquinoline, 10 g, 48.62 mmol) and H-1 (8-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)naphthalene-1-carboxylic acid ethyl ester (17.45 g, 53.48 mmol) respectively.

[0543] MS (m / z): 331.14

[0544] (2) Synthesis of compound D-12

[0545] [Reaction 12-2]

[0546]

[0547] The synthesis of compound D-9 was repeated to obtain compound D-12 (5.0 g, yield: 54%), except that compound C-12 (9.8 g, 29.51 mmol) was used instead of compound C-9 (9.9 g, 28.88 mmol).

[0548] MS (m / z): 311.13

[0549] (3) Synthesis of compound E-12

[0550] [Reaction 12-3]

[0551]

[0552] The synthesis of compound L-1 was repeated to obtain compound E-12 (3.4 g, yield: 55%), except that compound D-12 (5.0 g, 15.93 mmol) was used instead of compound K-1 (10.25 g, 30.37 mmol).

[0553] (4) Synthesis of compound 598

[0554] [Reaction 12-4]

[0555]

[0556] The synthesis of compound 369 was repeated to obtain compound 598 (1.6 g, yield: 39%), except that compound E-12 (3.4 g, 1.99 mmol) was used instead of compound L-1 (4.0 g, 2.21 mmol).

[0557] MS (m / z): 1024.38

[0558] Synthesis Example 13: Synthesis of compound RD1 (compound 4 in Formula 1-24)

[0559] (1) Synthesis of compound B-1

[0560] [Reaction Formula 13-1]

[0561]

[0562] Compound A-1 (1-chloro-6-isobutylisoquinoline, 10 g, 45.51 mmol), ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-2-naphthoate (16.3 g, 50.06 mmol), Pd(OAc)2 (0.51 g, 2.28 mmol), PPh3 (2.39 g, 0.91 mmol), K2CO3 (18.9 g, 136.53 mmol), 1-4-dioxane (100 mL), and water (100 mL) were stirred at 100 °C for 12 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate, and the water in the organic layer was removed with MgSO4. The mixture was then filtered under reduced pressure to remove the solvent. The mixture was purified by wet purification using hexane and ethyl acetate to obtain compound B-1 (10 g, 26.07 mmol). (Yield: 57%)

[0563] (2) Synthesis of compound C-1

[0564] [Reaction 13-2]

[0565]

[0566] Compound B-1 (ethyl 3-(6-isobutylisoquinoline-1-yl)-2-naphthoic acid, 10 g, 26.07 mmol) and THF (100 mL) were added, and CH3MgBr (15.5 g, 130 mmol) was slowly added at 0 °C. The reaction was terminated after 12 hours at room temperature. The mixture was extracted with ethyl acetate, water in the organic layer was removed with MgSO4, and the solvent was removed under reduced pressure. The mixture was purified by wet purification with hexane and ethyl acetate to give compound C-1 (7 g, 18.94 mmol). (Yield: 73%)

[0567] (3) Synthesis of compound D-1

[0568] [Reaction 13-3]

[0569]

[0570] Compound C-1 (2-(3-(6-isobutylisoquinolin-1-yl)naphth-2-yl)prop-2-ol, 10 g, 27.06 mmol) was added to a mixed aqueous solution of acetic acid and sulfuric acid (200 mL), and the mixture was refluxed and stirred for 16 hours. After the reaction was complete, the mixture was cooled to room temperature, and the reactants were slowly added to an aqueous solution of sodium hydroxide. The organic layer was extracted with dichloromethane and the water was removed with MgSO4, followed by removal of the organic solvent under reduced pressure. The mixture was recrystallized from toluene and ethanol to obtain a yellow solid compound D-1 (5 g, 14.22 mmol). (Yield: 53%)

[0571] (4) Synthesis of compound E-1

[0572] [Reaction 13-4]

[0573]

[0574] Compound D-1 (5-isobutyl-7,7-dimethyl-7H-benzo[de]naphtho[2,3-h]quinoline, 10 g, 28.45 mmol), 2-ethoxyethanol (200 mL), and distilled water (50 mL) were added, and nitrogen was introduced into the mixture for 1 hour. IrCl3·H2O (4.5 g, 12.93 mmol) was added to the reaction vessel and refluxed for 2 days. After the reaction was complete, the mixture was cooled to room temperature and filtered to obtain the solid. The solid was washed with methanol and dried to give compound E-1 (7.0 g, 6.05 mmol). (Yield: 21%)

[0575] (5) Synthesis of compound RD1

[0576] [Reaction 13-5]

[0577]

[0578] Compound E-1 (10 g, 8.64 mmol), 3,7-diethylnonane-4,6-dione (18.3 g, 86.4 mmol), and Na₂CO₃ (18.3 g, 172.8 mmol) were added and dissolved in 2-ethoxyethanol (100 mL). The mixture was stirred slowly for 24 hours. After the reaction was complete, the product was filtered through dichloromethane. After removing the solvent, the solid was filtered off. The filtered solid was added to isopropanol and stirred, then dried. Recrystallization and sublimation purification using dichloromethane and isopropanol gave compound RD1 (5 g, 4.53 mmol) in high purity (yield: 52%).

[0579] Synthesis Example 14: Synthesis of compound RD2 (compound 184 in Formula 1-25)

[0580] (1) Synthesis of compound B-2

[0581] [Reaction 14-1]

[0582]

[0583] Compound A-2 (1-chloro-6-isobutylisoquinoline, 10 g, 45.51 mmol), ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)-1-naphthoate (16.3 g, 50.06 mmol), Pd(OAc)2 (0.51 g, 2.28 mmol), PPh3 (2.39 g, 0.91 mmol), K2CO3 (18.9 g, 136.53 mmol), 1-4-dioxane (100 mL), and water (100 mL) were stirred at 100 °C for 12 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate, and the water in the organic layer was removed with MgSO4. The mixture was then filtered under reduced pressure to remove the solvent. The mixture was purified by wet purification using hexane and ethyl acetate to obtain compound B-2 (9 g, 23.47 mmol). (Yield: 52%)

[0584] (2) Synthesis of compound C-2

[0585] [Reaction 14-2]

[0586]

[0587] Compound B-2 (ethyl 2-(6-isobutylisoquinoline-1-yl)-1-naphthoate, 10 g, 26.07 mmol) and THF (100 mL) were added, and CH3MgBr (15.5 g, 130 mmol) was slowly added at 0 °C. The reaction was terminated after 12 hours at room temperature. The mixture was extracted with ethyl acetate, water in the organic layer was removed with MgSO4, and the solvent was removed under reduced pressure. The mixture was purified by wet purification with hexane and ethyl acetate to give compound C-2 (6 g, 16.23 mmol). (Yield: 62%)

[0588] (3) Synthesis of compound D-2

[0589] [Reaction 14-3]

[0590]

[0591] Compound C-2 (2-(2-(6-isobutylisoquinolin-1-yl)naphth-1-yl)prop-2-ol, 10 g, 27.06 mmol) was added to a mixed aqueous solution of acetic acid and sulfuric acid (200 mL). The mixture was refluxed and stirred for 16 hours. After the reaction was complete, the mixture was cooled to room temperature and slowly added to an aqueous solution of sodium hydroxide. The organic layer was extracted with dichloromethane and the water was removed with MgSO4. The organic solvent was then removed under reduced pressure. The mixture was recrystallized from toluene and ethanol to give compound D-2 (4 g, 11.38 mmol) as a yellow solid. (Yield: 42%)

[0592] (4) Synthesis of compound E-2

[0593] [Reaction 14-4]

[0594]

[0595] Compound D-2 (5-isobutyl-7,7-dimethyl-7H-benzo[de]naphtho[1,2-h]quinoline, 10 g, 28.45 mmol), 2-ethoxyethanol (200 mL), and distilled water (50 mL) were added, and nitrogen gas was introduced into the mixture for 1 hour. IrCl3·H2O (4.5 g, 12.93 mmol) was added to the reaction vessel and refluxed for 2 days. After the reaction was complete, the temperature was lowered to room temperature and the resulting solid was filtered. The solid was washed with methanol and dried to give compound E-2 (10 g, 8.65 mmol). (Yield: 30%)

[0596] (5) Synthesis of compound RD2

[0597] [Reaction 14-5]

[0598]

[0599] Compound E-2 (10 g, 8.64 mmol), 3,7-diethylnonane-4,6-dione (18.3 g, 86.4 mmol), and Na₂CO₃ (18.3 g, 172.8 mmol) were added and dissolved in 2-ethoxyethanol (100 mL). The mixture was stirred slowly for 24 hours. After the reaction was complete, the product was filtered through dichloromethane. After removing the solvent, the solid was filtered off. The filtered solid was added to isopropanol and stirred, then the filtered solid was dried. The mixture was recrystallized and purified using dichloromethane and isopropanol to give compound RD2 (4 g, 3.98 mmol) in high purity (yield: 46%).

[0600] Synthesis Example 15: Synthesis of compound RD3 (compound 371 in Formula 1-26)

[0601] (1) Synthesis of compound B-3

[0602] [Reaction Formula 15-1]

[0603]

[0604] Compound A-3 (5-bromoquinoline, 50 g, 240.33 mmol), isobutylboronic acid (49 g, 480.65 mmol), Pd2(dba)3 (6.6 g, 3 mol%), Sphos (2-bicyclohexylphosphine-2',6'-dimethoxydiphenyl, 9.9 g, 24.03 mmol), potassium phosphate monohydrate (276.71 g, 1.2 mol), and toluene (1000 mL) were stirred at 120 °C for 12 hours. After the reaction was complete, the mixture was cooled and extracted with ethyl acetate. After removing the solvent, the mixture was purified by wet purification with ethyl acetate and hexane to give compound B-3 (35 g, 188.92 mmol). (Yield: 79%)

[0605] (2) Synthesis of compound C-3

[0606] [Reaction 15-2]

[0607]

[0608] Compound B-3 (5-isobutylquinoline, 35 g, 188.92 mmol), 3-chloroperbenzoic acid (57 g, 283.38 mmol), and dichloromethane (500 mL) were stirred at room temperature for 3 hours. After the reaction was complete, sodium sulfite (80 g) was added to the mixture. The organic layer was extracted under reduced pressure to give compound C-3 (27 g, 134.15 mmol). (Yield: 71%)

[0609] (3) Synthesis of compound D-3

[0610] [Reaction 15-3]

[0611]

[0612] Compound C-3 (25 g, 124.22 mmol) and toluene (500 mL) were added, along with phosphorus trichloride (38.1 g, 248.44 mmol) and diisopropylethylamine (32.1 g, 248.44 mmol). The mixture was stirred at 120 °C for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane under reduced pressure. The mixture was filtered under reduced pressure using MgSO4 to remove the organic solvent. The mixture was then purified by wet filtration to obtain compound D-3 (30 g, 91.0 mmol). (Yield: 73%)

[0613] (4) Synthesis of compound E-3

[0614] [Reaction 15-4]

[0615]

[0616] Compound D-3 (10 g, 45.51 mmol), ethyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)naphthalene-1-carboxylate (16.33 g, 50.06 mmol), Pd(OAc)2 (0.5 g, 2.28 mmol), PPh3 (2.4 g, 9.10 mmol), K2CO3 (18.9 g, 136.53 mmol), 1,4-dioxane (100 mL), and water (100 mL) were stirred at 100 °C for 12 hours. After the reaction was complete, the mixture was extracted with ethyl acetate, and the water in the organic layer was removed with MgSO4. The solvent was removed from the mixture under reduced pressure. The mixture was purified by wet purification with hexane and ethyl acetate to obtain compound E-3 (13 g, 33.90 mmol). (Yield: 74%)

[0617] (5) Synthesis of compound F3

[0618] [Reaction 15-5]

[0619]

[0620] Compound E-3 (10 g, 26.07 mmol) and THF (100 mL) were added, followed by the slow addition of CH3MgBr (15.5 g, 130.35 mmol) at 0 °C. After the reaction proceeded at room temperature for 12 hours, the mixture was post-treated with ethyl acetate and MgSO4. The mixture was then purified by wet purification using hexane and ethyl acetate to obtain compound F-3 (6 g, 16.24 mmol). (Yield: 62%)

[0621] (5) Synthesis of compound G3

[0622] [Reaction Formula 15-6]

[0623]

[0624] Compound F-3 (20 g, 54.12 mmol) was added along with a mixed aqueous solution of acetic acid and sulfuric acid (200 mL), and the mixture was refluxed for 16 hours. After the reaction was complete, the reactants were slowly added to a cold aqueous solution of sodium hydroxide (cold sodium hydroxide). Following treatment with dichloromethane and MgSO4, the mixture was recrystallized from toluene and ethanol to give a yellow solid, compound G-3 (10 g, 28.45 mmol). (Yield: 53%)

[0625] (5) Synthesis of compound H3

[0626] [Reaction Formula 15-7]

[0627]

[0628] Compound G-3 (10 g, 28.45 mmol), 2-ethoxyethanol (200 mL), and distilled water (50 mL) were added, and nitrogen was purged for 1 hour. Then, IrCl3·H2O (4.5 g, 14.22 mmol) was added to the reaction vessel, and the mixture was refluxed for 2 days. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The solid was washed with hexane and methanol and dried to obtain compound H-3 (6.0 g, 5.19 mmol). (Yield: 18%)

[0629] (5) Synthesis of compound RD3

[0630] [Reaction 15-8]

[0631]

[0632] Compound H-3 (10 g, 8.64 mmol), 3,7-diethylnonane-4,6-dione (18.3 g, 86.4 mmol), and Na₂CO₃ (18.3 g, 172.8 mmol) were added and dissolved in 2-ethoxyethanol (100 mL). The mixture was stirred slowly for 24 hours. After the reaction was complete, the product was filtered through dichloromethane. After removing the solvent, the solid was filtered off. The filtered solid was added to isopropanol and the mixture was stirred. After stirring, the mixture was filtered off and the filtered solid was dried. The solid was recrystallized from dichloromethane and isopropanol to obtain compound RD3 (4 g, 3.62 mmol) with high purity. (Yield: 42%)

[0633] Synthesis Example 16: Synthesis of compound RD4 (compound 503 in Formula 1-27)

[0634] (1) Synthesis of compound B-4

[0635] [Reaction Formula 16-1]

[0636]

[0637] Compound A-4 (10 g, 45.51 mmol), ethyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborhecyclopentan-2-yl)naphthalene-1-carboxylate (16.33 g, 50.06 mmol), Pd(OAc)₂ (0.5 g, 2.28 mmol), PPh₃ (2.4 g, 9.10 mmol), K₂CO₃ (18.9 g, 136.53 mmol), 1,4-dioxane (100 mL), and water (100 mL) were stirred at 100 °C for 12 hours. After the reaction was complete, the mixture was extracted with ethyl acetate, and the water in the organic layer was removed with MgSO₄. The solvent was removed from the mixture under reduced pressure. The mixture was purified by wet purification using hexane and ethyl acetate to obtain compound B-4 (13 g, 33.90 mmol). (Yield: 74%)

[0638] (2) Synthesis of compound C-4

[0639] [Reaction 16-2]

[0640]

[0641] Compound B-4 (10 g, 26.07 mmol) and THF (100 mL) were added, followed by the slow addition of CH3MgBr (15.5 g, 130 mmol) at 0 °C. The reaction was carried out for 12 hours, and the mixture was post-treated with ethyl acetate and MgSO4. The mixture was then purified by wet purification using hexane and ethyl acetate to give compound C-4 (6 g, 16.24 mmol). (Yield: 62%)

[0642] (3) Synthesis of compound D-4

[0643] [Reaction 16-3]

[0644]

[0645] Compound C-4 (20 g, 54.12 mmol) was added to a mixed aqueous solution of acetic acid and sulfuric acid (200 mL), and the mixture was refluxed for 16 hours. After the reaction was complete, a cold aqueous solution of sodium hydroxide was slowly added to the mixture. The mixture was post-treated with dichloromethane and MgSO4. The mixture was recrystallized from toluene and ethanol to give compound D-4 (10 g, 28.45 mmol) as a yellow solid. (Yield: 53%)

[0646] (4) Synthesis of compound E-4

[0647] [Reaction 16-4]

[0648]

[0649] Compound D-4 (10 g, 28.45 mmol), 2-ethoxyethanol (200 mL), and distilled water (50 mL) were added, and nitrogen gas was introduced into the mixture for 1 hour. IrCl3·H2O (4.5 g, 14.22 mmol) was added to the reaction vessel and refluxed for 2 days. After the reaction was complete, the temperature was slowly lowered to room temperature, and the resulting solid was filtered. The solid was washed with methanol and dried to give compound E-4 (6.0 g, 5.19 mmol). (Yield: 18%)

[0650] (5) Synthesis of compound RD4

[0651] [Reaction 16-5]

[0652]

[0653] Compound E-4 (10 g, 8.64 mmol), 3,7-diethylnonane-4,6-dione (18.3 g, 86.4 mmol), and Na₂CO₃ (18.3 g, 172.8 mmol) were added and dissolved in 2-ethoxyethanol (100 mL). The mixture was stirred slowly for 24 hours. After the reaction was complete, the product was filtered through dichloromethane. After removing the solvent, the solid was filtered off. The filtered solid was added to isopropanol and stirred, then the filtered solid was dried. The mixture was recrystallized and purified using dichloromethane and isopropanol to give compound RD4 (4 g, 3.62 mmol) in high purity (yield: 42%).

[0654] Synthesis Example 17: Synthesis of compound RD17 (compound 610 in Formula 1-29)

[0655] [Reaction Formula 17]

[0656]

[0657] Compound A-17 (10 g, 5.38 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (12.94 g, 53.84 mmol), and Na₂CO₃ (11.4 g, 107.7 mmol) were added and dissolved in 2-ethoxyethanol (100 mL). The mixture was stirred slowly for 24 hours. After the reaction was complete, the product was filtered through dichloromethane. After removing the solvent, the solid was filtered off. The filtered solid was added to isopropanol and stirred, then the filtered solid was dried. The mixture was recrystallized from dichloromethane and isopropanol and purified to give compound RD17 (3.8 g, 3.36 mmol) in high purity (yield: 42%).

[0658] Synthesis Example 18: Synthesis of compound RD18 (compound 611 in Formula 1-29)

[0659] [Reaction Formula 18]

[0660]

[0661] Under nitrogen atmosphere, bromobenzene (1.01 g, 6.46 mmol) and 50 mL THF were added to a reaction vessel, and the mixture was cooled to -78 °C. Butyllithium (2.6 mL, 2.5 M hexane solution) was slowly added to the mixture. After 30 minutes, while maintaining the temperature, N,N'-diisopropylcarbodiimide (0.82 g, 6.46 mmol) was slowly added, and the mixture was stirred for 30 minutes. The mixture was then added to a reaction vessel in which compound A-18 (3 g, 1.62 mmol) was dissolved in 100 mL THF, and the mixture was stirred at 80 °C for 8 hours. The mixture was cooled to room temperature, and volatiles were removed. The mixture was purified by recrystallization using THF / pentane and dichloromethane / hexane to obtain compound RD18 (2.3 g, 2.03 mmol) of high purity.

[0662] Synthesis Example 19: Synthesis of compound RD19 (compound 612 in Formula 1-29)

[0663] [Reaction Formula 19]

[0664]

[0665] Under nitrogen atmosphere, compound A-19 (3 ​​g, 1.62 mmol) and THT (100 mL) were added to a reaction vessel, followed by the slow addition of compound F-1 (0.8 g, 3.56 mmol) dissolved in THF. The mixture was stirred at room temperature for 8 hours. The mixture was extracted with toluene to remove the solvent, and diethyl ether was added to obtain a solid. The obtained solid was purified to give compound RD19 (1.1 g, 1.01 mmol) in high purity.

[0666] Synthesis Example 20: Synthesis of compound RD20 (compound 613 in Formula 1-29)

[0667] [Reaction 20]

[0668]

[0669] Under nitrogen atmosphere, compound A-20 (3 g, 1.62 mmol) and THT (100 mL) were added to a reaction vessel, followed by the slow addition of compound F-2 (0.8 g, 3.56 mmol) dissolved in THF. The mixture was stirred at room temperature for 8 hours. The mixture was extracted with toluene to remove the solvent, and diethyl ether was added to obtain a solid. The obtained solid was purified to give compound RD20 (0.9 g, 0.80 mmol) in high purity.

[0670] Synthesis Example 21: Synthesis of compound RD21 (compound 614 in Formula 1-29)

[0671] [Reaction 21]

[0672]

[0673] Compound A-21 (10 g, 5.38 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (12.94 g, 53.84 mmol), and Na₂CO₃ (11.4 g, 107.7 mmol) were added and dissolved in 2-ethoxyethanol (100 mL). The mixture was stirred slowly for 24 hours. After the reaction was complete, the product was filtered through dichloromethane. After removing the solvent, the solid was filtered off. The filtered solid was added to isopropanol and stirred, and then the filtered solid was dried. The mixture was recrystallized from dichloromethane and isopropanol to obtain high-purity compound RD2 (3.4 g, 3.00 mmol).

[0674] Synthesis Example 22: Synthesis of compound RD22 (compound 615 in Formula 1-29)

[0675] [Reaction 22]

[0676]

[0677] Under nitrogen atmosphere, bromobenzene (1.01 g, 6.46 mmol) and 50 mL of THF were added to a reaction vessel, and the mixture was cooled to -78 °C. Butyllithium (2.6 mL, 2.5 M hexane solution) was slowly added to the mixture. After 30 minutes, while maintaining the temperature, N,N'-diisopropylcarbodiimide (0.82 g, 6.46 mmol) was slowly added, and the mixture was stirred for 30 minutes. The mixture was then added to a reaction vessel in which compound A-22 (3 g, 1.62 mmol) was dissolved in 100 mL of THF, and the mixture was stirred at 80 °C for 8 hours. The mixture was cooled to room temperature, and volatile substances were removed. The mixture was recrystallized from THF / pentane and dichloromethane / hexane and purified to obtain compound RD22 (2.0 g, 1.82 mmol) in high purity.

[0678] Synthesis Example 23: Synthesis of compound RD23 (compound 616 in Formula 1-29)

[0679] [Reaction 23]

[0680]

[0681] Under nitrogen atmosphere, compound A-23 (3 g, 1.62 mmol) and THT (100 mL) were added to a reaction vessel, followed by the slow addition of compound F-1 (0.8 g, 3.56 mmol) dissolved in THF. The mixture was stirred at room temperature for 8 hours. The mixture was extracted with toluene to remove the solvent, and diethyl ether was added to give a solid. The obtained solid was purified to give compound RD23 (2.5 g, 2.29 mmol) in high purity.

[0682] Synthesis Example 24: Synthesis of compound RD24 (compound 617 in Formula 1-29)

[0683] [Reaction 24]

[0684]

[0685] Under nitrogen atmosphere, compound A-24 (3 g, 1.62 mmol) and THT (100 mL) were added to a reaction vessel, followed by the slow addition of compound F-2 (0.8 g, 3.56 mmol) dissolved in THF. The mixture was stirred at room temperature for 8 hours. The mixture was extracted with toluene to remove the solvent, and diethyl ether was added to obtain a solid. The obtained solid was purified to give compound RD24 (2.2 g, 1.95 mmol) in high purity.

[0686] Synthesis Example 25: Synthesis of compound RD25 (compound 618 in Formula 1-29)

[0687] [Reaction 25]

[0688]

[0689] Compound A-25 (10 g, 5.38 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (12.94 g, 53.84 mmol), and Na₂CO₃ (11.4 g, 107.7 mmol) were added and dissolved in 2-ethoxyethanol (100 mL). The mixture was stirred slowly for 24 hours. After the reaction was complete, the product was filtered through dichloromethane. After removing the solvent, the solid was filtered off. The filtered solid was added to isopropanol and stirred, and then the filtered solid was dried. The mixture was recrystallized from dichloromethane and isopropanol to obtain high-purity compound RD25 (3.3 g, 2.91 mmol).

[0690] Synthesis Example 26: Synthesis of compound RD26 (compound 619 in Formula 1-29)

[0691] [Reaction 26]

[0692]

[0693] Under nitrogen atmosphere, bromobenzene (1.01 g, 6.46 mmol) and 50 mL of THF were added to a reaction vessel, and the mixture was cooled to -78 °C. Butyllithium (2.6 mL, 2.5 M hexane solution) was slowly added to the mixture. After 30 minutes, while maintaining the temperature, N,N'-diisopropylcarbodiimide (0.82 g, 6.46 mmol) was slowly added, and the mixture was stirred for 30 minutes. The mixture was then added to a reaction vessel in which compound A-26 (3 g, 1.62 mmol) was dissolved in 100 mL of THF, and the mixture was stirred at 80 °C for 8 hours. The mixture was cooled to room temperature, and volatile substances were removed. The mixture was purified by recrystallization from THF / pentane and dichloromethane / hexane to give high-purity compound RD26 (2.1 g, 1.92 mmol).

[0694] Synthesis Example 27: Synthesis of compound RD27 (compound 620 in Formula 1-29)

[0695] [Reaction 27]

[0696]

[0697] Under nitrogen atmosphere, compound A-27 (3 g, 1.62 mmol) and THT (100 mL) were added to a reaction vessel, followed by the slow addition of compound F-1 (0.8 g, 3.56 mmol) dissolved in THF. The mixture was stirred at room temperature for 8 hours. The mixture was extracted with toluene to remove the solvent, and diethyl ether was added to obtain a solid. The obtained solid was purified to give compound RD27 (2.2 g, 2.02 mmol) in high purity.

[0698] Synthesis Example 28: Synthesis of compound RD28 (compound 621 in Formulas 1-29)

[0699] [Reaction 28]

[0700]

[0701] Under nitrogen atmosphere, compound A-28 (3 g, 1.62 mmol) and THT (100 mL) were added to a reaction vessel, followed by the slow addition of compound F-2 (0.8 g, 3.56 mmol) dissolved in THF. The mixture was stirred at room temperature for 8 hours. The mixture was extracted with toluene to remove the solvent, and diethyl ether was added to obtain a solid. The obtained solid was purified to give compound RD28 (1.9 g, 1.68 mmol) in high purity.

[0702] Synthesis Example 29: Synthesis of compound RD29 (compound 622 in Formulas 1-29)

[0703] [Reaction 29]

[0704]

[0705] Compound A-29 (10 g, 5.38 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (12.94 g, 53.84 mmol), and Na₂CO₃ (11.4 g, 107.7 mmol) were added and dissolved in 2-ethoxyethanol (100 mL). The mixture was stirred slowly for 24 hours. After the reaction was complete, the product was filtered through dichloromethane. After removing the solvent, the solid was filtered off. The filtered solid was added to isopropanol and stirred, and then the filtered solid was dried. The mixture was recrystallized from dichloromethane and isopropanol to obtain high-purity compound RD29 (3.9 g, 3.44 mmol).

[0706] Synthesis Example 30: Synthesis of compound RD30 (compound 623 in Formula 1-29)

[0707] [Reaction 30]

[0708]

[0709] Under nitrogen atmosphere, bromobenzene (1.01 g, 6.46 mmol) and 50 mL of THF were added to a reaction vessel, and the mixture was cooled to -78 °C. Butyllithium (2.6 mL, 2.5 M hexane solution) was slowly added to the mixture. After 30 minutes, while maintaining the temperature, N,N'-diisopropylcarbodiimide (0.82 g, 6.46 mmol) was slowly added, and the mixture was stirred for 30 minutes. The mixture was then added to a reaction vessel in which compound A-30 (3 g, 1.62 mmol) was dissolved in 100 mL of THF, and the mixture was stirred at 80 °C for 8 hours. The mixture was cooled to room temperature, and volatile substances were removed. The mixture was purified by recrystallization from THF / pentane and dichloromethane / hexane to give high-purity compound RD30 (2.7 g, 2.46 mmol).

[0710] Synthesis Example 31: Synthesis of compound RD31 (compound 624 in Formula 1-29)

[0711] [Reaction Formula 31]

[0712]

[0713] Under nitrogen atmosphere, compound A-31 (3 g, 1.62 mmol) and THT (100 mL) were added to a reaction vessel, followed by the slow addition of compound F-1 (0.8 g, 3.56 mmol) dissolved in THF. The mixture was stirred at room temperature for 8 hours. The mixture was extracted with toluene to remove the solvent, and diethyl ether was added to obtain a solid. The obtained solid was purified to give compound RD31 (2.0 g, 1.84 mmol) in high purity.

[0714] Synthesis Example 32: Synthesis of compound RD32 (compound 625 in Formula 1-29)

[0715] [Reaction 32]

[0716]

[0717] Under nitrogen atmosphere, compound A-32 (3 g, 1.62 mmol) and THT (100 mL) were added to a reaction vessel, followed by the slow addition of compound F-2 (0.8 g, 3.56 mmol) dissolved in THF. The mixture was stirred at room temperature for 8 hours. The mixture was extracted with toluene to remove the solvent, and diethyl ether was added to obtain a solid. The obtained solid was purified to give compound RD32 (1.8 g, 1.59 mmol) in high purity.

[0718] The second compound 234 has excellent hole-dominant properties (characteristics) and is represented by Formula 2-1.

[0719] [Equation 2-1]

[0720]

[0721] X and Y are each independently selected from deuterated or undeuterated unsubstituted or substituted C6-C. 30 Aryl and deuterated or undeuterated unsubstituted or substituted C3-C 30 Group composed of heteroaryl groups.

[0722] R 4 Choose unsubstituted or substituted C1-C, whether deuterated or undeuterated. 10 Alkyl groups and deuterated or undeuterated unsubstituted or substituted C6-C 30 A group composed of aryl groups.

[0723] a1 is an integer between 0 and 9.

[0724] L 1 Choose C6-C, either unsubstituted or substituted. 30 aryl and unsubstituted or substituted C3-C 30 Groups composed of heteroarylene groups, and

[0725] a2 is 0 or 1.

[0726] Each of X, Y, and L1 can be partially or completely replaced by deuterium.

[0727] X and Y can be the same or different. The aryl and heteroaryl groups of X and Y can be deuterated, C6-C... 30 Aryl and C3-C 30 At least one of the heteroaryl groups is substituted.

[0728] For example, X and Y can each be independently selected from unsubstituted or deuterated, C6-C. 30 Aryl and C3-C 30 At least one substituted phenyl group in the heteroaryl group, unsubstituted or deuterated, C6-C 30 Aryl and C3-C 30 At least one substituted biphenyl in the heteroaryl group, unsubstituted or deuterated, C6-C 30 Aryl and C3-C 30 At least one substituted naphthyl group in the heteroaryl group, either unsubstituted or C1-C2 substituted. 20 Alkyl or C6-C 30 The group consisting of aryl-substituted fluorenyl groups (e.g., 9,9-dimethyl-9H-fluorenyl or 9,9-diphenyl-9H-fluorenyl), phenanthrene groups, and dibenzofuranyl and dibenzothiophene groups. R 1 It can be phenyl, and L1 can be selected from the group consisting of unsubstituted or deuterated phenylene, unsubstituted or deuterated naphthylene, and unsubstituted or deuterated biphenylene.

[0729] In Equation 2-1, R can be specified. 1The connection position. That is, Equation 2-1 can be represented by Equation 2-2.

[0730] [Equation 2-2]

[0731]

[0732] in

[0733] X and Y are each independently selected from either deuterated or undeuterated unsubstituted or substituted C6-C. 30 Aryl and deuterated or undeuterated unsubstituted or substituted C3-C 30 Group composed of heteroaryl groups.

[0734] R 4 Choose unsubstituted or substituted C1-C, whether deuterated or undeuterated. 10 Alkyl groups and deuterated or undeuterated unsubstituted or substituted C6-C 30 A group composed of aryl groups.

[0735] L 1 Choose C6-C, either unsubstituted or substituted. 30 aryl and unsubstituted or substituted C3-C 30 The group composed of heteroarylene groups, and

[0736] a2 is 0 or 1.

[0737] Alternatively, in Equation 2-1, X may include at least two aromatic rings, and optionally, the two aromatic rings may be fused. That is, Equation 2-1 can be represented by Equation 2-3.

[0738] [Equation 2-3]

[0739]

[0740] in

[0741] Y is selected from either deuterated or undeuterated, unsubstituted, or C6-C. 30 Aryl and C3-C 30 At least one substituted phenyl group, deuterated or undeuterated, or C6-C substituted phenyl group. 30 Aryl and C3-C 30 At least one substituted biphenyl, deuterated or undeuterated, or C6-C substituted biphenyl in the heteroaryl group. 30 Aryl and C3-C 30 The group consisting of at least one substituted naphthyl group in heteroaryl groups.

[0742] R 4 Choose C1-C, either unsubstituted or substituted. 10 Alkyl and unsubstituted or substituted C6-C 30 A group composed of aryl groups.

[0743] a1 is an integer from 0 to 9.

[0744] R 5 and R 6 Each is independently selected from hydrogen and unsubstituted or substituted C6-C. 30 A group composed of aryl groups.

[0745] Optionally,

[0746] R 5 and R 6 Formation of heterocyclic aromatic rings,

[0747] L 1 Choose C6-C, either unsubstituted or substituted. 30 aryl and unsubstituted or substituted C3-C 30 The group composed of heteroarylene groups, and

[0748] a2 is 0 or 1.

[0749] For example, L1 can be phenylene or biphenylene, and a2 can be 1. Additionally, from R... 5 and R 6 The resulting heteroaromatic rings may include oxygen atoms (O).

[0750] For example, the second compound 234 could be one of the compounds in formula 2-4.

[0751] [Equation 2-4]

[0752]

[0753]

[0754]

[0755]

[0756] The third compound 236 has excellent electronic dominance properties and is represented by Formula 3-1.

[0757] [Equation 3-1]

[0758]

[0759] in

[0760] M is an oxygen atom (O) or a sulfur atom (S);

[0761] Q and Z are each independently selected from either deuterated or undeuterated unsubstituted or substituted C6-C. 30 Aryl and deuterated or undeuterated unsubstituted or substituted C3-C30 Group composed of heteroaryl groups;

[0762] L 2 Choose either the unsubstituted or substituted C6-C. 30 aryl groups and unsubstituted or substituted C3-C 30 The group composed of heteroarylene groups; and

[0763] b is 0 or 1.

[0764] C6-C 30 Aryl, C3-C 30 heteroaryl, C6-C 30 aryl and C3-C 30 Heteroarylene can be deuterated, C1-C 10 Alkyl or C6-C 30 At least one of the aryl groups is substituted.

[0765] For example, Q and Z can be the same or different, and Q and Z are each independently chosen to be unsubstituted or replaced by deuterium and C6-C. 30 The group consisting of aryl-substituted phenyl, naphthyl, dibenzofuranyl, dibenzothiopheneyl, 9,9-dimethylfluorenyl, phenylcarbazoyl, and phenanthreneyl groups. L2 can be phenylene or naphthylene.

[0766] In one exemplary embodiment, Q may be phenyl or naphthyl, and Z may be naphthyl.

[0767] For example, the third compound 236 of formula 3-1 can be represented by formula 3-2.

[0768] [Equation 3-2]

[0769]

[0770] In one exemplary embodiment, M can be O and b can be 1. That is, the third compound 236 of formula 3-2 can be represented by formula 3-3.

[0771] [Equation 3-3]

[0772]

[0773] For example, the third compound 236 could be one of the compounds in formula 3-4.

[0774] [Equation 3-4]

[0775]

[0776]

[0777]

[0778]

[0779] HIL 210 is located between the first electrode 160 and HTL 220. HIL 210 may include 4,4',4”-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4”-tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4',4”-tris(N-(naphthyl-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4”-tris(N-(naphthyl-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazolyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4”-diamine (NPB) Or NPD), 1,4,5,8,9,11-hexaazabenzonitrile (dipyrazine[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbamate (HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene)polystyrene sulfonate (PEDOT / PSS), and N-(biphenyl-4-yl))-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine, but not limited thereto. HIL 210 may have 10 to The thickness is preferably 50 to

[0780] HTL 220 is located between HIL 210 and Red EML 230. HTL 220 may include N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), NPB (or NPD), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)-benzidine] (poly-TPD), poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))] (TFB), di-[4-(N,N-di-p-tolyl-amino)-phenyl]cyclohexane (TAPC), and 3,5-bis(9H-carbazol-9-yl)-N,N-diphenylaniline (DCDPA).

[0781] N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl))

[0782] -9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)

[0783] At least one compound from the group consisting of biphenyl-4-amine and compounds of formula 4, but not limited thereto. HTL 220 may have 500 to The thickness is preferably 600 to

[0784] [Formula 4]

[0785]

[0786] ETL 240 is located between red EML 230 and second electrode 164, and includes at least one of the following: oxadiazole compounds, triazole compounds, phenanthrene-rhein compounds, benzoxazole compounds, benzothiazole compounds, benzimidazole compounds, and triazine compounds. For example, ETL... 240 may include, selected from, tris-(8-hydroxyquinoline aluminum (Alq3), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, lithium quinoline (Liq), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-di(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl 1,2,4-Triazole (TAZ), 4-(naphth-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 1,3,5-tris(p-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), poly[9,9-bis(3'-(N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene]-alt-2,7-(9,9-dioctylfluorene)](PFNBr), tris(phenylquinoxaline) (TPQ), and diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide (TSPO1), but not limited thereto. ETL 240 may have 100 to The thickness is preferably 200 to

[0787] EIL 250 is located between ETL 240 and the second electrode 164. EIL 250 is at least one, but not limited to, alkali metal halide compounds (e.g., LiF, CsF, NaF, or BaF2) and organometallic compounds (e.g., Liq, lithium benzoate, or sodium stearate). EIL 250 may have 1 to The thickness is preferably 5 to 10 mm.

[0788] Located between HTL 220 and red EML 230 to prevent electrons from transferring from red EML 230 to HTL. The EBL of 220 may include, but is not limited to, at least one compound selected from the group consisting of TCTA, tris[4-(diethylamino)phenyl]amine, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, TAPC, MTDATA, 1,3-bis(carbazole-9-yl)phenyl (mCP), 3,3'-bis(N-carbazole)-1,1'-biphenyl (mCBP), CuPc, N,N'-bis[4-(bis(3-methylphenyl))amino)phenyl]-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD), TDAPB, DCDPA, and 2,8-bis(9-phenyl-9H-carbazole-3-yl)dibenzo[b,d]thiophene.

[0789] The HBL located between ETL 240 and red EML 230 to prevent holes from transferring from red EML 230 to ETL 240 may include the aforementioned material of ETL 240. For example, the HOMO level of the HBL material is lower than that of the red EML 230 material, and it may be at least one compound selected from, but not limited to, the group consisting of BCP, BAlq, Alq3, PBD, spiro-PBD, Liq, bis-4,6-(3,5-di-3-pyridylphenyl)-2-methylpyrimidine (B3PYMPM), bis[2-(diphenylphosphino)phenyl] ether oxide (DPEPO), 9-(6-9H-carbazole-9-yl)pyridin-3-yl)-9H-3,9'-bicarbazole and TSPO1.

[0790] As described above, OLED D1 is located in the red pixel region. The red EML 230 of OLED D1 includes a first compound 232 represented by Formula 1-1 as a dopant, a second compound 234 represented by Formula 2-1 as a first host or p-type host, and a third compound 236 represented by Formula 3-1 as a second host or n-type host. Therefore, in OLED D1, the driving voltage is reduced, and the luminous efficiency and luminous lifetime are increased.

[0791] Figure 4This is a cross-sectional view showing an OLED according to a third embodiment of the present invention.

[0792] like Figure 4 As shown, OLED D2 includes a first electrode 160 and a second electrode 164 facing each other, and an organic light-emitting layer 162 between them. The organic light-emitting layer 162 includes a first light-emitting portion 710 containing a first red EML 720 and a second light-emitting portion 730 containing a second red EML 740. In addition, the organic light-emitting layer 162 may also include a charge-generating layer (CGL) 750 between the first and second light-emitting portions 710 and 730.

[0793] For example, the first electrode 160 may include a transparent conductive material, such as ITO or IZO, and the second electrode 164 may include one of Al, Mg, Ag, AlMg, and MgAg.

[0794] CGL 750 is located between the first and second light-emitting portions 710 and 730, such that the first light-emitting portion 710, CGL 750 and the second light-emitting portion 730 are stacked sequentially on the first electrode 160. That is, the first light-emitting portion 710 is located between the first electrode 160 and CGL 750, and the second light-emitting portion 730 is located between the second electrode 164 and CGL 750.

[0795] As shown below, the first light-emitting part 710 includes a first red EML 720. The first red EML 720 includes a first compound 722 as a red dopant (e.g., a red emitter), a second compound 724 as a p-type host (e.g., a first host), and a third compound 726 as an n-type host (e.g., a second host). In the first red EML 720, the first compound 722 is represented by Formula 1-1, the second compound 724 by Formula 2-1, and the third compound 726 by Formula 3-1.

[0796] The first red EML 720 can have 100 to The thickness can be, for example, 200 to 400, but is not limited to.

[0797] In the first red EML 720, the weight percentage of each of the second and third compounds 724 and 726 is greater than that of the first compound 722. For example, in the first red EML 720, the first compound 722 may have 1-20% by weight, for example 5-15% by weight.

[0798] Furthermore, in the first red EML 720, the weight percentage ratio of the second compound 724 to the third compound 726 can be from 1:3 to 3:1. For example, in the first red EML 720, the second and third compounds 724 and 726 can have the same weight percentage.

[0799] The first light-emitting portion 710 may further include at least one of a first HTL 714 below the first red EML 720 and a first ETL 716 on or above the first red EML 720. That is, the first HTL 714 is disposed between the first red EML 720 and the first electrode 160, and the first ETL 716 is disposed between the first red EML 720 and the CGL 750.

[0800] In addition, the first light-emitting part 710 may also include a HIL 712 between the first electrode 160 and the first HTL 714.

[0801] As shown below, the second light-emitting part 730 includes a second red EML 740. The second red EML 740 includes a first compound 742 (e.g., a fourth compound) as a red dopant (e.g., a red emitter), a second compound 744 (e.g., a fifth compound) as a p-type host (e.g., a first host), and a third compound 726 (e.g., a sixth compound) as an n-type host (e.g., a second host). In the second red EML 740, the first compound 742 is represented by Formula 1-1, the second compound 744 by Formula 2-1, and the third compound 746 by Formula 3-1.

[0802] The second red EML 740 can have 100 to The thickness can be, for example, 200 to 400, but is not limited to.

[0803] In the second red EML 740, the weight percentage of each of the second and third compounds 744 and 746 may be greater than that of the first compound 742. For example, in the second red EML 740, the first compound 742 has 1-20% by weight, for example 5-15% by weight.

[0804] Furthermore, in the second red EML 740, the weight percentage ratio of the second compound 744 to the third compound 746 can be from 1:3 to 3:1. For example, in the second red EML 740, the second and third compounds 744 and 746 can have the same weight percentage.

[0805] The first compound 742 in the second red EML 740 and the first compound 722 in the first red EML 720 may be the same or different. The second compound 744 in the second red EML 740 and the second compound 724 in the first red EML 720 may be the same or different. The third compound 746 in the second red EML 740 and the third compound 726 in the first red EML 720 may be the same or different.

[0806] The second light-emitting portion 730 may further include at least one of a second HTL 732 below the second red EML 740 and a second ETL 734 on or above the second red EML 740. That is, the second HTL 732 is disposed between the second red EML 740 and CGL 750, and the second ETL 734 is disposed between the second red EML 740 and the second electrode 164.

[0807] In addition, the second light-emitting part 730 may also include an EIL 736 between the second ETL 734 and the second electrode 164.

[0808] CGL 750 is located between the first and second light-emitting portions 710 and 730. That is, the first and second light-emitting portions 710 and 730 are connected to each other through CGL 750. CGL 750 can be a PN junction type CGL, such as N-type CGL 752 or P-type CGL 754.

[0809] The N-type CGL 752 is located between the first ETL 716 and the second HTL 732, and the P-type CGL 754 is located between the N-type CGL 752 and the second HTL 732.

[0810] In OLED D2, at least one of the first and second red EMLs 720 and 740 includes a first compound represented by Formula 1-1 (e.g., a red dopant), a second compound represented by Formula 2-1 (e.g., a p-type host), and a third compound represented by Formula 3-1 (e.g., an n-type host). Therefore, OLED D2 has advantages in terms of driving voltage, luminous efficiency, and luminous lifetime.

[0811] Figure 5 This is a cross-sectional view showing an organic light-emitting display device according to a fourth embodiment of the present invention.

[0812] like Figure 5 As shown, the organic light-emitting display device 300 includes a first substrate 310 defining a red pixel region RP, a green pixel region GP and a blue pixel region BP, a second substrate 370 facing the first substrate 310, an OLED D located between the first substrate 310 and the second substrate 370 and providing white light emission, and a color filter layer 380 located between the OLED D and the second substrate 370.

[0813] Each of the first substrate 310 and the second substrate 370 may be a glass substrate or a flexible substrate. For example, each of the first and second substrates 310 and 370 may be a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylene naphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate, or a polycarbonate (PC) substrate.

[0814] A buffer layer 320 is formed on the substrate, and a corresponding TFT Tr is formed on the buffer layer 320 for each of the red pixel area RP, the green pixel area GP, and the blue pixel area BP. The buffer layer 320 can be omitted.

[0815] Semiconductor layer 322 is formed on buffer layer 320. Semiconductor layer 322 may include oxide semiconductor material or polysilicon.

[0816] A gate insulating layer 324 is formed on the semiconductor layer 322. The gate insulating layer 324 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride.

[0817] A gate electrode 330, formed of a conductive material such as metal, is formed on the gate insulating layer 324 to correspond to the center of the semiconductor layer 322.

[0818] An interlayer insulating layer 332, formed of an insulating material, is formed on the gate electrode 330. The interlayer insulating layer 332 may be formed of an inorganic insulating material (e.g., silicon oxide or silicon nitride) or an organic insulating material (e.g., benzocyclobutene or photopropylene).

[0819] The interlayer insulating layer 332 includes a first contact hole 334 and a second contact hole 336 exposing both sides of the semiconductor layer 322. The first contact hole 334 and the second contact hole 336 are located on both sides of the gate electrode 330 and spaced apart from the gate electrode 330.

[0820] A source electrode 340 and a drain electrode 342, formed of a conductive material such as metal, are formed on an interlayer insulating layer 332.

[0821] The source electrode 340 and the drain electrode 342 are spaced apart from each other relative to the gate electrode 330 and contact both sides of the semiconductor layer 322 through the first and second contact holes 334 and 336, respectively.

[0822] Semiconductor layer 322, gate electrode 330, source electrode 340, and drain electrode 342 constitute TFT Tr. TFT Tr serves as a driving element. That is, TFT Tr can correspond to driving TFT Td ( Figure 1 ).

[0823] Although not shown, the gate lines and data lines intersect to define the pixel, and the switching TFT is connected to the gate lines and data lines. The switching TFT is connected to the TFT Tr, which serves as a driving element.

[0824] Furthermore, a power supply line spaced parallel to one of the gate line and the data line can be formed, as well as a storage capacitor for maintaining the voltage of the gate electrode of the TFT Tr in a frame.

[0825] A planarization layer 350 is formed to cover the TFT Tr, the planarization layer 350 including a drain contact hole 352 that exposes the drain 342 of the TFT Tr.

[0826] First electrodes 360, connected to the drain 342 of the TFT Tr via drain contact holes 352, are formed in each pixel region and on the planarization layer 350. The first electrode 360 ​​can be an anode and can be formed of a conductive material with a relatively high work function, such as a transparent conductive oxide (TCO). The first electrode 360 ​​may also include a reflective electrode or a reflective layer. For example, the reflective electrode or reflective layer may include Ag or aluminum-palladium-copper (APC). In the top-emitting organic light-emitting display device 300, the first electrode 360 ​​may have an ITO / Ag / ITO or ITO / APC / ITO structure.

[0827] A dam layer 366 is formed on the planarization layer 350 to cover the edge of the first electrode 360. That is, the dam layer 366 is located at the boundary of the pixel and exposed to the center of the first electrode 360 ​​within the pixel. Since the OLED D emits white light in the red, green, and blue pixel regions RP, GP, and BP, the organic light-emitting layer 362 can be formed as a universal layer in the red, green, and blue pixel regions RP, GP, and BP without separation. The dam layer 366 can be formed to prevent current leakage at the edge of the first electrode 360 ​​and can be omitted.

[0828] An organic light-emitting layer 362 is formed on the first electrode 360. As shown in the figure below, the organic light-emitting layer 362 includes at least two light-emitting portions, each of which includes at least one EML. As a result, the OLED D emits white light.

[0829] At least one light-emitting part includes a first compound, such as a red dopant, represented by Formula 1-1, a second compound, such as a p-type host or a first host, represented by Formula 2-1, and a third compound, such as an n-type host or a second host, represented by Formula 3-1, to emit red light.

[0830] A second electrode 364 is formed above the substrate 310 on which the organic light-emitting layer 362 is formed.

[0831] In the organic light-emitting display device 300, since light emitted from the organic light-emitting layer 362 is incident on the color filter layer 380 through the second electrode 364, the second electrode 364 has a thin profile for transmitting light.

[0832] The first electrode 360, the organic light-emitting layer 362, and the second electrode 364 constitute an OLED D.

[0833] The color filter layer 380 is located above the OLED D and includes a red color filter 382, ​​a green color filter 384, and a blue color filter 386 corresponding to the red, green, and blue pixel regions RP, GP, and BP, respectively. The red color filter 382 may include at least one of red dye and red pigment, the green color filter 384 may include at least one of green dye and green pigment, and the blue color filter 386 may include at least one of blue dye and blue pigment.

[0834] Although not shown, the color filter layer 380 can be attached to the OLED D using an adhesive layer. Alternatively, the color filter layer 380 can be formed directly on the OLED D.

[0835] An encapsulation film (not shown) can be formed to prevent moisture from penetrating into the OLED D. For example, the encapsulation film may include, but is not limited to, a first inorganic insulating layer, an organic insulating layer, and a second inorganic insulating layer stacked sequentially. The encapsulation film may be omitted.

[0836] A polarizer (not shown) for reducing ambient light reflection can be mounted on the top-emitting OLED D. For example, the polarizer can be a circular polarizer.

[0837] exist Figure 5 In the OLED, the first and second electrodes 360 and 364 are a reflective electrode and a transparent (or semi-transparent) electrode, respectively, and a color filter layer 380 is disposed above the OLED D. Alternatively, when the first and second electrodes 360 and 364 are a transparent (or semi-transparent) electrode and a reflective electrode, respectively, the color filter layer 380 can be disposed between the OLED D and the first substrate 310.

[0838] A color conversion layer (not shown) may be formed between the OLED D and the color filter layer 380. The color conversion layer may include a red conversion layer, a green conversion layer, and a blue conversion layer corresponding to the red, green, and blue pixel regions RP, GP, and BP, respectively. White light emitted by the OLED D is converted into red, green, and blue light, respectively, by the red, green, and blue color conversion layers. For example, the color conversion layer may include quantum dots. Therefore, the color purity of the organic light-emitting display device 300 can be further improved.

[0839] A color conversion layer may be included to replace the color filter layer 380.

[0840] As described above, in the organic light-emitting display device 300, the OLED D in the red, green, and blue pixel regions RP, GP, and BP emits white light, and the white light from the organic light-emitting diode D passes through the red color filter 382, ​​the green color filter 384, and the blue color filter 386. As a result, red light, green light, and blue light are provided from the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP, respectively.

[0841] exist Figure 5 In this embodiment, an OLED D emitting white light is used as a display device. Alternatively, an OLED D can be formed on the entire surface of a substrate without at least one of a driving element and a color filter layer for use as a light-emitting device. Display devices and light-emitting devices each incorporating the OLED D of the present invention can be referred to as organic light emitters.

[0842] Figure 6 This is a cross-sectional view showing an OLED according to a fifth embodiment of the present invention.

[0843] like Figure 6 As shown, in OLED D3, the organic light-emitting layer 362 includes: a first light-emitting portion 430 including a red EML 410, a second light-emitting portion 440 including a first blue EML 450, and a third light-emitting portion 460 including a third blue EML 470. Furthermore, the organic light-emitting layer 362 may also include a first CGL 480 between the first and second light-emitting portions 430 and 440, and a second CGL 490 between the first and third light-emitting portions 430 and 460. Additionally, the first light-emitting portion 430 may also include a green EML 420.

[0844] The first electrode 360 ​​is the anode, and the second electrode 364 is the cathode. One of the first electrode 360 ​​and the second electrode 364 can be a transparent (semi-transparent) electrode, and the other of the first electrode 360 ​​and the second electrode 364 can be a reflective electrode.

[0845] The second light-emitting part 440 is located between the first electrode 360 ​​and the first light-emitting part 430, and the third light-emitting part 460 is located between the first light-emitting part 430 and the second electrode 364. Furthermore, the second light-emitting part 440 is located between the first electrode 360 ​​and the first CGL 480, and the third light-emitting part 460 is located between the second CGL 490 and the second electrode 364. That is, the second light-emitting part 440, the first CGL 480, the first light-emitting part 430, the second CGL 460, and the third light-emitting part 460 are sequentially stacked on the first electrode 360.

[0846] In the first light-emitting part 430, the green EML 420 is located on the red EML 410.

[0847] The first light-emitting portion 430 may further include at least one of a first HTL 432 below the red EML 410 and a first ETL 434 above the red EML 410. When the first light-emitting portion 430 includes a green EML 420, the first ETL 434 is located on the green EML 420.

[0848] The second light-emitting portion 440 may further include at least one of a second HTL 444 below the first blue EML 450 and a second ETL 448 on the first blue EML 450. Furthermore, the second light-emitting portion 440 may also include a HIL 442 between the first electrode 360 ​​and the first HTL 444.

[0849] Although not shown, the second light-emitting portion 440 may also include at least one of a first EBL between the second HTL 444 and the first blue EML 450 and a first HBL between the first blue EML 450 and the second ETL 448.

[0850] The third light-emitting portion 460 may further include at least one of a third HTL 462 below the second blue EML 470 and a third ETL 466 on the second blue EML 470. Furthermore, the third light-emitting portion 460 may also include an EIL 468 between the second electrode 364 and the third ETL 466.

[0851] Although not shown, the third light-emitting part 460 may also include at least one of the first EBL between the third HTL 462 and the second blue EML 470 and the first HBL between the second blue EML 470 and the third EML 466.

[0852] For example, HIL 442 may include at least one of MTDATA, NATA, 4,4',4”-tris(N-(naphthyl-1-yl)-N-phenyl-amino)triphenylamine 1T-NATA, 2T-NATA, CuPc, TCTA, NPB, HAT-CN, TDAPB, PEDOT / PSS, and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl))phenyl)-9H-fluorene-2-amine.

[0853] Each of the first to third HTLs 432, 444 and 464 may include at least one of TPD, NPB, CBP, poly-TPD, TFB, TAPC, DCDPA, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H)-carbazole-3-yl)phenyl)biphenyl-4-amine, and a compound of formula 4.

[0854] Each of the first to third ETLs 434, 448 and 466 may include at least one of Alq3, PBD, spiro-PBD, Liq, TPBi, BAlq, Bphen, NBphen, BCP, TAZ, NTAZ, TpPyPB, TmPPPyTz, PFNBr, TPQ and TSPO1.

[0855] EIL 468 may include at least one of an alkali metal halide compound (e.g., LiF, CsF, NaF, or BaF2) and an organometallic compound (e.g., Liq, lithium benzoate, or sodium stearate).

[0856] The first CGL 480 is located between the first and second light-emitting portions 430 and 440, and the second CGL 490 is located between the first and third light-emitting portions 430 and 460. That is, the first and second light-emitting portions 430 and 440 are connected to each other through the first CGL 480, and the first and third light-emitting portions 430 and 460 are connected to each other through the second CGL 490. The first CGL 480 can be a PN junction type CGL of N-type CGL 482 and P-type CGL 484, and the second CGL 490 can be a PN junction type CGL of N-type CGL 492 and P-type CGL 494.

[0857] In the first CGL 480, the N-type CGL 482 is located between the first HTL 432 and the second ETL 448, and the P-type CGL 484 is located between the N-type CGL 482 and the first HTL 432.

[0858] In the second CGL 490, the N-type CGL 492 is located between the first ETL 434 and the third HTL 462, and the P-type CGL 494 is located between the N-type CGL 492 and the third HTL 462.

[0859] Each of the N-type CGL 482 of the first CGL 480 and the N-type CGL 492 of the second CGL 490 may be an organic layer doped with an alkali metal (e.g., Li, Na, K, or Cs) and / or an alkaline earth metal (e.g., Mg, Sr, Ba, or Ra). For example, each of the N-type CGL 482 of the first CGL 480 and the N-type CGL 492 of the second CGL 490 may include an organic material, such as 4,7-diphenyl-1,10-phenanthroline (Bphen) or MTDATA as the host, and an alkali metal and / or an alkaline earth metal as a dopant may be doped from about 0.01 to 30% by weight.

[0860] Each of the p-type CGL 484 of the first CGL 480 and the p-type CGL 494 of the second CGL 490 may include at least one inorganic material and an organic material, wherein the inorganic material is selected from tungsten oxide (WOx), molybdenum oxide (MoOx), beryllium oxide (Be2O3), vanadium oxide (V2O5) and combinations thereof, and wherein the organic material is selected from NPD, HAT-CN, F4TCNQ, TPD, N,N,N'N'-tetranaphthalenebenzidine (TNB), TCTA, N,N'-dioctyl-3,4,9,10-perylenedicarboximide (PTCDI-C8) and combinations thereof.

[0861] Red EML 410 includes a first compound 412 as a red dopant (e.g., a red emitter), a second compound 414 as a p-type host (e.g., a first host), and a third compound 416 as an n-type host (e.g., a second host). In red EML 410, the first compound 412 is represented by Formula 1-1, the second compound 414 by Formula 2-1, and the third compound 416 by Formula 3-1.

[0862] In red EML 410, the weight percentage of each of the second and third compounds 414 and 416 can be greater than that of the first compound 412. For example, in red EML 410, the first compound 412 can have 1-20% by weight, for example 5-15% by weight.

[0863] Furthermore, in Red EML 410, the weight percentage ratio between the second compound 414 and the third compound 416 can be from 1:3 to 3:1. For example, in Red EML 410, the second and third compounds 414 and 416 can have the same weight percentage.

[0864] In the first light-emitting part 410, the green EML 420 includes a green host and a green dopant. The green dopant can be one of a phosphorescent compound, a fluorescent compound, and a delayed fluorescence compound. For example, in the green EML 420, the host can be 4,4'-bis(carbazole-9-yl)biphenyl (CBP), and the green dopant can be a faceted tris(2-phenylpyridine)iridiumIr(ppy)3 or tris(8-hydroxyquinoline)aluminum (Alq3).

[0865] The first blue EML 450 in the second light-emitting part 440 includes a first blue body and a first blue dopant, and the second blue EML 470 in the third light-emitting part 460 includes a second blue body and a second blue dopant.

[0866] For example, the first and second blue bodies can each be independently selected from mCP, 9-(3-(9H-carbazole-9-yl)phenyl)-9H-carbazole-3-onitrile (mCP-CN)), mCBP, CBP-CN, 9-(3-(9H-carbazole-9-yl)phenyl)-3-(diphenylphosphoyl)-9H-carbazole (mCPPO1), 3,5-bis(9H-carbazole-9-yl)biphenyl (Ph-mCP), TSPO1, 9-(3'-(9H-carbazole-9-yl)-[ The group consisting of 1,1'-biphenyl]-3-yl)-9H-pyrido[2,3-b]indole (CzBPCb), bis(2-methylphenyl)diphenylsilane (UGH-1), 1,4-bis(triphenylsilyl)benzene (UGH-2), 1,3-bis(triphenylsilyl)benzene (UGH-3), 9,9-spirofluorene-2-acyldiphenylphosphine oxide (SPPO1) and 9,9'-(5-(triphenylsilyl)-1,3-phenyl)bis(9h-carbazole) (SimCP).

[0867] For example, the first and second blue dopants can be independently selected from perylene, 4,4'-bis[4-(diphenyl)phenyl]biphenyl (DPAVBi), 4-(diphenyl)phenyl-4-(diphenyl)phenyl]stilbene (DPAVB), 4,4'-bis[4-(diphenyl)phenyl]biphenyl (BDAVBi), 2,7-bis(4-diphenyl)phenyl)-9,9-spirofluorene (spiro-DPVBi), [1,4-bis[2-[4-[N,N-diphenyl)amino]phenyl]benzene (DSB), 1,4-bis[4-(N,N-diphenyl)amino]phenyl]benzene (DSA), 2,5,8,11-tetra-tetrabutylperylene (TBPe), bis(2-hydroxyphenyl)pyridine beryllium (Bepp2), 9-(9 The group consisting of 1,3-phenylcarbazol-3-yl)-10-(naphth-1-yl)anthracene (PCAN), poly-tris(1-phenyl-3-methylimidazol-2-methylene-C,C(2)'iridium(III))(mer-Ir(pmi)3), facet-tris(1,3-diphenyl-benzimidazole-2-methylene-C,C(2)'iridium(III))(fac-Ir(dpbic)3), bis-3,4,5-trifluoro-2-(2-pyridine)phenyl-(2-carboxypyridyl)iridium(III))(Ir(tfpd)2pic), tris(2-(4,6-difluorophenyl)pyridine)iridium(III))(Ir(Fppy)3) and bis[2-(4,6-difluorophenyl)pyridine-c2,N](pyridine)iridium(III))(FIrpic).

[0868] In one exemplary aspect, each of the first and second blue EMLs 450 and 470 may include an anthracene derivative as the blue body and a boron derivative as the blue dopant.

[0869] As described above, the OLED D3 of the present invention includes: a first light-emitting portion 430 including a red EML 410 and a green EML 420, a second light-emitting portion 440 including a first blue EML 450, and a third light-emitting portion 460 including a second blue EML 470. As a result, the OLED D3 emits white light.

[0870] Furthermore, the red EML 410 includes a first compound 412 represented by Formula 1-1 as a red dopant, a second compound 414 represented by Formula 2-1 as a first host or p-type host, and a third compound 416 represented by Formula 3-1 as a second host or n-type host. Therefore, OLED D3 has advantages in driving voltage, luminous efficiency, and luminous lifetime.

[0871] Figure 7 This is a cross-sectional view showing an OLED according to a sixth embodiment of the present invention.

[0872] like Figure 7 As shown, in OLED D4, the organic light-emitting layer 362 includes: a first light-emitting portion 530 including a red EML 510, a green EML 520, and a yellow-green EML 525; a second light-emitting portion 540 including a first blue EML 550; and a third light-emitting portion 560 including a third blue EML 570. Furthermore, the organic light-emitting layer 362 may also include a first CGL 580 between the first and second light-emitting portions 530 and 540, and a second CGL 590 between the first and third light-emitting portions 530 and 560.

[0873] The first electrode 360 ​​is the anode, and the second electrode 364 is the cathode. One of the first electrode 360 ​​and the second electrode 364 can be a transparent (semi-transparent) electrode, and the other of the first electrode 360 ​​and the second electrode 364 can be a reflective electrode.

[0874] The second light-emitting part 540 is located between the first electrode 360 ​​and the first light-emitting part 530, and the third light-emitting part 560 is located between the first light-emitting part 530 and the second electrode 364. Furthermore, the second light-emitting part 540 is located between the first electrode 360 ​​and the first CGL 580, and the third light-emitting part 560 is located between the second CGL 590 and the second electrode 364. That is, the second light-emitting part 540, the first CGL 580, the first light-emitting part 530, the second CGL 560, and the third light-emitting part 560 are sequentially stacked on the first electrode 360.

[0875] In the first light-emitting part 530, the yellow-green EML 525 is located between the red EML 510 and the green EML 520. That is, the red EML 510, the yellow-green EML 525 and the green EML 520 are stacked in sequence, so that the first light-emitting part 530 includes an EML with a three-layer structure.

[0876] The first light-emitting part 530 may also include at least one of a first HTL 532 below the red EML 510 and a first ETL 534 above the red EML 510.

[0877] The second light-emitting portion 540 may further include at least one of a second HTL 544 below the first blue EML 550 and a second ETL 548 on the first blue EML 550. Furthermore, the second light-emitting portion 540 may also include a HIL 542 between the first electrode 360 ​​and the first HTL 544.

[0878] Although not shown, the second light-emitting portion 540 may also include at least one of a first EBL between the second HTL 544 and the first blue EML 550 and a first HBL between the first blue EML 550 and the second ETL 548.

[0879] The third light-emitting portion 560 may further include at least one of a third HTL 562 below the second blue EML 570 and a third ETL 566 on the second blue EML 570. Furthermore, the third light-emitting portion 560 may also include an EIL 568 between the second electrode 364 and the third ETL 566.

[0880] Although not shown, the third light-emitting portion 560 may also include at least one of the first EBL between the third HTL 562 and the second blue EML 570, and the first HBL between the second blue EML 570 and the third EML 566.

[0881] For example, HIL 542 may include at least one of MTDATA, NATA, 4,4',4”-tris(N-(naphthyl-1-yl)-N-phenyl-amino)triphenylamine 1T-NATA, 2T-NATA, CuPc, TCTA, NPB, HAT-CN, TDAPB, PEDOT / PSS, and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl))phenyl)-9H-fluorene-2-amine.

[0882] Each of the first to third HTLs 532, 544 and 564 may include at least one of TPD, NPB, CBP, poly-TPD, TFB, TAPC, DCDPA, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H)-carbazole-3-yl)phenyl)biphenyl-4-amine, and a compound of formula 4.

[0883] Each of the first to third ETLs 534, 548 and 566 may include at least one of Alq3, PBD, spiro-PBD, Liq, TPBi, BAlq, Bphen, NBphen, BCP, TAZ, NTAZ, TpPyPB, TmPPPyTz, PFNBr, TPQ and TSPO1.

[0884] EIL 568 may include at least one of an alkali metal halide compound (e.g., LiF, CsF, NaF, or BaF2) and an organometallic compound (e.g., Liq, lithium benzoate, or sodium stearate).

[0885] The first CGL 580 is located between the first and second light-emitting portions 530 and 540, and the second CGL 590 is located between the first and third light-emitting portions 530 and 560. That is, the first and second light-emitting portions 530 and 540 are connected to each other through the first CGL 580, and the first and third light-emitting portions 530 and 560 are connected to each other through the second CGL 590. The first CGL 580 can be a PN junction type CGL of N-type CGL 582 and P-type CGL 584, and the second CGL 590 can be a PN junction type CGL of N-type CGL 592 and P-type CGL 594.

[0886] In the first CGL 580, the N-type CGL 582 is located between the first HTL 532 and the second ETL 548, and the P-type CGL 584 is located between the N-type CGL 582 and the first HTL 532.

[0887] In the second CGL590, the N-type CGL592 is located between the first ETL534 and the third HTL562, and the P-type CGL594 is located between the N-type CGL592 and the third HTL562.

[0888] Each of the N-type CGL582 of the first CGL 580 and the N-type CGL 592 of the second CGL 590 may be an organic layer doped with an alkali metal (e.g., Li, Na, K, or Cs) and / or an alkaline earth metal (e.g., Mg, Sr, Ba, or Ra). For example, each of the N-type CGL582 of the first CGL 580 and the N-type CGL 592 of the second CGL 590 may include an organic material, such as 4,7-diphenyl-1,10-phenanthroline (Bphen) or MTDATA as the host, and an alkali metal and / or an alkaline earth metal as a dopant may be doped at about 0.01 to 30% by weight.

[0889] Each of the P-type CGL 584 of the first CGL 580 and the P-type CGL 594 of the second CGL 590 may include at least one of inorganic and organic materials, wherein the inorganic material is selected from tungsten oxide (WOx), molybdenum oxide (MoOx), beryllium oxide (Be2O3), vanadium oxide (V2O5) and combinations thereof, and wherein the organic material is selected from NPD, HAT-CN, F4TCNQ, TPD, N,N,N'N'-tetranaphthalenebenzidine (TNB), TCTA, N,N'-dioctyl-3,4,9,10-perylenedicarboximide (PTCDI-C8) and combinations thereof.

[0890] Red EML 510 includes a first compound 512 as a red dopant (e.g., a red emitter), a second compound 514 as a p-type host (e.g., a first host), and a third compound 516 as an n-type host (e.g., a second host). In red EML 510, the first compound 512 is represented by Formula 1-1, the second compound 514 by Formula 2-1, and the third compound 516 by Formula 3-1.

[0891] In red EML 510, the weight percentage of each of the second and third compounds 514 and 516 can be greater than that of the first compound 512. For example, in red EML 510, the first compound 512 can have 1-20% by weight, such as 5-15% by weight.

[0892] Furthermore, in Red EML 510, the weight percentage ratio between the second compound 514 and the third compound 516 can be from 1:3 to 3:1. For example, in Red EML 510, the second and third compounds 514 and 516 can have the same weight percentage.

[0893] In the first light-emitting unit 510, the green EML 520 includes a green substrate and a green dopant. The green dopant can be one of a phosphorescent compound, a fluorescent compound, and a delayed fluorescence compound. Furthermore, in the first light-emitting unit 510, the yellow-green EML 525 includes a yellow-green substrate and a yellow-green dopant. The yellow-green dopant can be one of a phosphorescent compound, a fluorescent compound, and a delayed fluorescence compound.

[0894] The first blue EML 550 in the second light-emitting part 540 includes a first blue body and a first blue dopant, and the second blue EML 570 in the third light-emitting part 560 includes a second blue body and a second blue dopant.

[0895] For example, the first and second blue subjects can each be independently selected from the group consisting of mCP, mCP-CN, mCBP, CBP-CN, mCPPO1, Ph-mCP, TSPO1, CzBPCb, UGH-1, UGH-2, UGH-3, SPPO1 and SimCP.

[0896] For example, the first and second blue dopants can be independently selected from the group consisting of perylene, DPAVBi, DPAVB, BDAVBi, spiro-DPVBi, DSB, DSA, TBPe, Bepp2, PCAN, mer-Ir(pmi)3, fac-Ir(dpbic)3, Ir(tfpd)2pic, Ir(Fppy)3, and Firpic.

[0897] In one exemplary aspect, each of the first and second blue EMLs 550 and 570 may include an anthracene derivative as the blue body and a boron derivative as the blue dopant.

[0898] As described above, the OLED D4 of the present invention includes: a first light-emitting portion 530 including a red EML 510 and a green EML 520, a second light-emitting portion 540 including a first blue EML 550, and a third light-emitting portion 560 including a second blue EML 570. As a result, the OLED D4 emits white light.

[0899] Furthermore, the red EML 510 includes a first compound 512 represented by Formula 1-1 as a red dopant, a second compound 514 represented by Formula 2-1 as a first host or p-type host, and a third compound 516 represented by Formula 3-1 as a second host or n-type host. Therefore, OLED D4 has advantages in driving voltage, luminous efficiency, and luminous lifetime.

[0900] Figure 8 This is a cross-sectional view showing an OLED according to a seventh embodiment of the present invention.

[0901] like Figure 8 As shown, in OLED D5, the organic light-emitting layer 362 includes: a first light-emitting portion 630 including a red EML 610 and a green EML 620, and a second light-emitting portion 640 including a first blue EML 650. Furthermore, the organic light-emitting layer 362 may also include a CGL 660 between the first and second light-emitting portions 630 and 640.

[0902] The first electrode 360 ​​is the anode, and the second electrode 364 is the cathode. One of the first electrode 360 ​​and the second electrode 364 can be a transparent (semi-transparent) electrode, and the other of the first electrode 360 ​​and the second electrode 364 can be a reflective electrode.

[0903] The first light-emitting part 630 is located between CGL 660 and the second electrode 364, and the second light-emitting part 640 is located between CGL 660 and the first electrode 360. Alternatively, the first light-emitting part 630 may be located between CGL 660 and the first electrode 360, and the second light-emitting part 640 may be located between CGL 660 and the second electrode 364.

[0904] In the first light-emitting part 630, the green EML 620 is located on the red EML 610.

[0905] The first light-emitting portion 630 may further include at least one of a first HTL 632 below the red EML 610 and a first ETL 634 above the red EML 610. When the first light-emitting portion 630 includes a green EML 620, the first ETL 634 is located on the green EML 620. Furthermore, the first light-emitting portion 630 may also include an EIL 636 between the first ETL 634 and the second electrode 364.

[0906] The second light-emitting portion 640 may further include at least one of a second HTL 644 below the blue EML 650 and a second ETL 646 on the blue EML 650. Furthermore, the second light-emitting portion 640 may also include a HIL 642 between the first electrode 360 ​​and the first HTL 644.

[0907] For example, HIL 642 may include at least one of MTDATA, NATA, 4,4',4”-tris(N-(naphthyl-1-yl)-N-phenyl-amino)triphenylamine 1T-NATA, 2T-NATA, CuPc, TCTA, NPB, HAT-CN, TDAPB, PEDOT / PSS, and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine.

[0908] Each of the first and second HTLs 632 and 644 may include at least one of TPD, NPB, CBP, poly-TPD, TFB, TAPC, DCDPA, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)biphenyl-4-amine, and a compound of formula 4.

[0909] Each of the first and second ETLs 634 and 646 may include at least one of Alq3, PBD, spiro-PBD, Liq, TPBi, BAlq, Bphen, NBphen, BCP, TAZ, NTAZ, TpPyPB, TmPPPyTz, PFNBr, TPQ, and TSPO1.

[0910] EIL 636 may include at least one of an alkali metal halide compound (e.g., LiF, CsF, NaF, or BaF2) and an organometallic compound (e.g., Liq, lithium benzoate, or sodium stearate).

[0911] CGL 660 is located between the first and second light-emitting parts 630 and 640. That is, the first and second light-emitting parts 630 and 640 are connected to each other through CGL 660.

[0912] CGL 660 can be a PN junction type CGL of N-type CGL 662 and P-type CGL 664.

[0913] In CGL 660, N-type CGL 662 is located between the first HTL 632 and the second ETL 646, and P-type CGL 664 is located between N-type CGL 662 and the first HTL 632.

[0914] N-type CGL 662 can be an organic layer doped with an alkali metal (e.g., Li, Na, K, or Cs) and / or an alkaline earth metal (e.g., Mg, Sr, Ba, or Ra). For example, N-type CGL 662 may include an organic material (e.g., 4,7-diphenyl-1,10-phenanthroline (Bphen) or MTDATA) as the host, and the alkali metal and / or alkaline earth metal as dopants may be doped at about 0.01 to 30% by weight.

[0915] P-type CGL 664 may include at least one of inorganic and organic materials, wherein the inorganic material is selected from tungsten oxide (WOx), molybdenum oxide (MoOx), beryllium oxide (Be2O3), vanadium oxide (V2O5) and combinations thereof, and wherein the organic material is selected from NPD, HAT-CN, F4TCNQ, TPD, N,N,N'N'-tetranaphthalenebenzidine (TNB), TCTA, N,N'-dioctyl-3,4,9,10-perylenedicarboximide (PTCDI-C8) and combinations thereof.

[0916] Red EML 610 includes a first compound 612 as a red dopant (e.g., a red emitter), a second compound 614 as a p-type host (e.g., a first host), and a third compound 616 as an n-type host (e.g., a second host). In Red EML 610, the first compound 612 is represented by Formula 1-1, the second compound 614 by Formula 2-1, and the third compound 616 by Formula 3-1.

[0917] In red EML 610, the weight percentage of each of the second and third compounds 614 and 616 can be greater than that of the first compound 612. For example, in red EML 610, the first compound 612 can have 1-20% by weight, for example 5-15% by weight.

[0918] Furthermore, in Red EML 610, the weight percentage ratio of the second compound 614 to the third compound 616 can be from 1:3 to 3:1. For example, in Red EML 610, the second and third compounds 614 and 616 can have the same weight percentage.

[0919] In the first light-emitting part 610, the green EML 620 includes a green body and a green dopant. The green dopant can be one of a phosphorescent compound, a fluorescent compound, and a delayed fluorescence compound.

[0920] The blue EML 650 in the second light-emitting part 640 includes a blue body and a blue dopant.

[0921] For example, the blue host can be selected from the group consisting of mCP, mCP-CN, mCBP, CBP-CN, mCPPO1, Ph-mCP, TSPO1, CzBPCb, UGH-1, UGH-2, UGH-3, SPPO1, and SimCP, and the blue dopant can be selected from the group consisting of perylene, DPAVBi, DPAVB, BDAVBi, spiro-DPVBi, DSB, DSA, TBPe, Bepp2, PCAN, mer-Ir(pmi)3, fac-Ir(dpbic)3, Ir(tfpd)2pic, Ir(Fppy)3, and Firpic.

[0922] In one exemplary aspect, the blue EML 650 may include an anthracene derivative as the blue host and a boron derivative as the blue dopant.

[0923] As described above, the OLED D5 of the present invention includes a first light-emitting portion 630 comprising a red EML 610 and a green EML 620, and a second light-emitting portion 640 comprising a blue EML 650. As a result, the OLED D5 emits white light.

[0924] Furthermore, the red EML 610 comprises a first compound 612 represented by Formula 1-1 as a red dopant, a second compound 614 represented by Formula 2-1 as a first host or p-type host, and a third compound 616 represented by Formula 3-1 as a second host or n-type host. Therefore, OLED D5 has advantages in driving voltage, luminous efficiency, and luminous lifetime.

[0925] [OLED]

[0926] Anode (ITO), HIL (HATCN (compound in Formula 5), HTL (the compound in Formula 4), ), EML (body and dopant (10wt%), ),ETL(Alq3, EIL(LiF, ) and cathode (Al, The layers are deposited sequentially. An encapsulation film is formed by using UV-cured epoxy resin and a hygroscopic agent to form an OLED.

[0927] [Formula 5]

[0928]

[0929] [Formula 6]

[0930]

[0931] [Formula 7]

[0932]

[0933] [Formula 8]

[0934]

[0935]

[0936]

[0937]

[0938] 1. Comparative Example 1 (Ref 1)

[0939] Compound RD1 in Formula 8 and compound (CBP) in Formula 7 are used as dopant and host, respectively, to form EML.

[0940] 2. Example

[0941] (1) Examples 1 to 6 (Ex1 to Ex6)

[0942] Compound RD1 from Formula 8 is used as a dopant, compound RHH-2 from Formulas 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formulas 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[0943] (2) Examples 7 to 12 (Ex7 to Ex12)

[0944] Compound RD1 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[0945] (3) Examples 13 to 18 (Ex13 to Ex18)

[0946] Compound RD1 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[0947] (4) Examples 19 to 24 (Ex19 to Ex24)

[0948] Compound RD1 from Formula 8 is used as a dopant, compound RHH-17 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[0949] (5) Examples 25 to 30 (Ex25 to Ex30)

[0950] Compound RD1 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[0951] (6) Examples 31 to 36 (Ex31 to Ex36)

[0952] Compound RD1 from Formula 8 is used as a dopant, compound RHH-27 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[0953] The characteristics of the OLEDs manufactured in Comparative Example 1 and Examples 1 to 36, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Tables 1 and 2. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[0954] Table 1

[0955]

[0956]

[0957] Table 2

[0958]

[0959]

[0960] As shown in Tables 1 and 2, compared with the OLED of Ref1 (where the red EML includes compound RD1 as a dopant and CBP as the host), the OLEDs of Ex1 to Ex36 (where the red EML includes compound RD1 as a dopant, compounds RHH-2, RHH-5, RHH-11, RHH-17, RHH-22 and RHH-27 as the first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[0961] 3. Comparative Example 2 (Ref 2)

[0962] Compound RD2 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form the EML.

[0963] 4. Example

[0964] (1) Examples 37 to 42 (Ex37 to Ex42)

[0965] Compound RD2 from Formula 8 is used as a dopant, compound RHH-2 from Formula 2-4 is used as the first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[0966] (2) Examples 43 to 48 (Ex43 to Ex48)

[0967] Compound RD2 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[0968] (3) Examples 49 to 54 (Ex49 to Ex54)

[0969] Compound RD2 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[0970] (4) Examples 55 to 60 (Ex55 to Ex60)

[0971] Compound RD2 from Formula 8 is used as a dopant, compound RHH-17 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[0972] (5) Examples 61 to 66 (Ex61 to Ex66)

[0973] Compound RD2 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[0974] (6) Examples 67 to 72 (Ex67 to Ex72)

[0975] Compound RD2 from Formula 8 is used as a dopant, compound RHH-27 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[0976] The characteristics of the OLEDs manufactured in Comparative Examples 2 and Examples 37 to 72, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Tables 3 and 4. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[0977] Table 3

[0978]

[0979]

[0980] Table 4

[0981]

[0982]

[0983] As shown in Tables 3 and 4, compared with the OLED of Ref2 (where the red EML includes compound RD2 as a dopant and CBP as the host), the OLEDs of Ex37 to Ex72 (where the red EML includes compound RD2 as a dopant, compounds RHH-2, RHH-5, RHH-11, RHH-17, RHH-22 and RHH-27 as the first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[0984] 5. Comparative Example 3 (Ref 3)

[0985] Compound RD3 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form the EML.

[0986] 6. Example

[0987] (1) Examples 73 to 78 (Ex73 to Ex78)

[0988] Compound RD3 from Formula 8 is used as a dopant, compound RHH-2 from Formulas 2-4 is used as the first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formulas 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[0989] (2) Examples 79 to 84 (Ex79 to Ex84)

[0990] Compound RD3 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[0991] (3) Examples 85 to 90 (Ex85 to Ex90)

[0992] Compound RD3 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[0993] (4) Examples 91 to 96 (Ex91 to Ex96)

[0994] Compound RD3 from Formula 8 is used as a dopant, compound RHH-17 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[0995] (5) Examples 97 to 102 (Ex97 to Ex102)

[0996] Compound RD3 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[0997] (6) Examples 103 to 108 (Ex103 to Ex108)

[0998] Compound RD3 from Formula 8 is used as a dopant, compound RHH-27 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[0999] The characteristics of the OLEDs manufactured in Comparative Examples 3 and Examples 73 to 108, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Tables 5 and 6. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1000] Table 5

[1001]

[1002]

[1003] Table 6

[1004]

[1005] As shown in Tables 5 and 6, compared with the OLED of Ref3 (where the red EML includes compound RD3 as a dopant and CBP as the host), the OLEDs of Ex73 to Ex108 (where the red EML includes compound RD3 as a dopant, compounds RHH-2, RHH-5, RHH-11, RHH-17, RHH-22 and RHH-27 as the first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1006] 7. Comparative Example 4 (Ref 4)

[1007] Compound RD4 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form the EML.

[1008] 8. Examples

[1009] (1) Examples 109 to 114 (Ex109 to Ex114)

[1010] Compound RD4 from Formula 8 is used as a dopant, compound RHH-2 from Formulas 2-4 is used as the first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formulas 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1011] (2) Examples 115 to 120 (Ex115 to Ex120)

[1012] Compound RD4 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1013] (3) Examples 121 to 126 (Ex121 to Ex126)

[1014] Compound RD4 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1015] (4) Examples 127 to 132 (Ex127 to Ex132)

[1016] Compound RD4 from Formula 8 is used as a dopant, compound RHH-17 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1017] (5) Examples 133 to 138 (Ex133 to Ex138)

[1018] Compound RD4 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1019] (6) Examples 139 to 144 (Ex139 to Ex144)

[1020] Compound RD4 from Formula 8 is used as a dopant, compound RHH-24 from Formula 2-4 is used as a first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1021] The characteristics of the OLEDs manufactured in Comparative Example 4 and Examples 109 to 144, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Tables 7 and 8. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1022] Table 7

[1023]

[1024]

[1025] Table 8

[1026]

[1027] As shown in Tables 7 and 8, compared with the OLED of Ref4 (where the red EML includes compound RD4 as a dopant and CBP as the host), the OLEDs of Ex109 to Ex144 (where the red EML includes compound RD4 as a dopant, compounds RHH-2, RHH-5, RHH-11, RHH-17, RHH-22 and RHH-27 as the first host, and compounds REH-1, REH-7, REH-12, REH-21, REH-27 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1028] 9. Comparative Example 5 (Ref 5)

[1029] Compound RD5 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form the EML.

[1030] 10. Example

[1031] (1) Examples 145 to 147 (Ex145 to Ex147)

[1032] Compound RD5 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1033] (2) Examples 148 to 150 (Ex148 to Ex150)

[1034] Compound RD5 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1035] (3) Examples 151 to 153 (Ex151 to Ex153)

[1036] Compound RD5 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1037] The characteristics of the OLEDs manufactured in Comparative Example 5 and Examples 145 to 153, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 9. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1038] Table 9

[1039]

[1040]

[1041] As shown in Table 9, compared with the OLED of Ref5 (where the red EML includes compound RD5 as a dopant and CBP as the host), the OLEDs of Ex145 to Ex153 (where the red EML includes compound RD5 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1042] 11. Comparative Example 6 (Ref 6)

[1043] Compound RD6 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form the EML.

[1044] 12. Example

[1045] (1) Examples 154 to 156 (Ex154 to Ex156)

[1046] Compound RD6 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1047] (2) Examples 157 to 159 (Ex157 to Ex159)

[1048] Compound RD6 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1049] (3) Examples 160 and 162 (Ex160 and Ex162)

[1050] Compound RD6 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1051] The characteristics of the OLEDs manufactured in Comparative Example 6 and Examples 154 to 162, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 10. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm².2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1052] Table 10

[1053]

[1054] As shown in Table 10, compared with the OLED of Ref6 (where the red EML includes compound RD6 as a dopant and CBP as the host), the OLEDs of Ex154 to Ex162 (where the red EML includes compound RD6 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1055] 13. Comparative Example 7 (Ref 7)

[1056] Compound RD7 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form the EML.

[1057] 14. Example

[1058] (1) Examples 163 to 165 (Ex169 to Ex170)

[1059] Compound RD7 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1060] (2) Examples 166 to 168 (Ex166 to Ex168)

[1061] Compound RD7 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1062] (3) Examples 169 to 171 (Ex169 to Ex171)

[1063] Compound RD7 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1064] The characteristics of the OLEDs manufactured in Comparative Example 7 and Examples 163 to 171, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 11. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1065] Table 11

[1066]

[1067] As shown in Table 11, compared with the OLED of Ref7 (where the red EML includes compound RD7 as a dopant and CBP as the host), the OLEDs of Ex163 to Ex171 (where the red EML includes compound RD7 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1068] 15. Comparative Example 8 (Ref 8)

[1069] Compound RD8 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form the EML.

[1070] 16. Example

[1071] (1) Examples 172 to 174 (Ex172 to Ex174)

[1072] Compound RD8 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1073] (2) Examples 175 to 177 (Ex175 to Ex177)

[1074] Compound RD8 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1075] (3) Examples 178 to 180 (Ex178 to Ex180)

[1076] Compound RD8 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1077] The characteristics of the OLEDs manufactured in Comparative Examples 8 and Examples 172 to 180, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 12. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1078] Table 12

[1079]

[1080]

[1081] As shown in Table 12, compared with the Ref8 OLED (where the red EML includes compound RD8 as a dopant and CBP as the host), the Ex172 to Ex180 OLEDs (where the red EML includes compound RD8 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1082] 17. Comparative Example 9 (Ref 9)

[1083] Compound RD9 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form the EML.

[1084] 18. Example

[1085] (1) Examples 181 to 183 (Ex181 to Ex183)

[1086] Compound RD9 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1087] (2) Examples 184 to 186 (Ex184 to Ex186)

[1088] Compound RD9 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1089] (3) Examples 187 to 189 (Ex187 to Ex189)

[1090] Compound RD9 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1091] The characteristics of the OLEDs manufactured in Comparative Example 9 and Examples 181 to 189, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 13. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1092] Table 13

[1093]

[1094] As shown in Table 13, compared with the Ref9 OLED (where the red EML includes compound RD9 as a dopant and CBP as the host), the Ex181 to Ex189 OLEDs (where the red EML includes compound RD9 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1095] 19. Comparative Example 10 (Ref 10)

[1096] Compound RD10 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form the EML.

[1097] 20. Example

[1098] (1) Examples 190 to 192 (Ex190 to Ex192)

[1099] Compound RD10 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1100] (2) Examples 193 to 195 (Ex193 to Ex195)

[1101] Compound RD10 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1102] (3) Examples 196 to 198 (Ex196 to Ex198)

[1103] Compound RD10 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1104] The characteristics of the OLEDs manufactured in Comparative Example 10 and Examples 190 to 198, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 14. The characteristics of the OLEDs were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1105] Table 14

[1106]

[1107] As shown in Table 14, compared with the OLED of Ref10 (where the red EML includes compound RD10 as a dopant and CBP as the host), the OLEDs of Ex190 to Ex198 (where the red EML includes compound RD10 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1108] 21. Comparative Example 11 (Ref 11)

[1109] Compound RD11 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form the EML.

[1110] 22. Example

[1111] (1) Examples 199 to 201 (Ex199 to Ex201)

[1112] Compound RD11 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1113] (2) Examples 202 to 204 (Ex202 to Ex204)

[1114] Compound RD11 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1115] (3) Examples 205 to 207 (Ex205 to Ex207)

[1116] Compound RD11 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1117] The characteristics of the OLEDs manufactured in Comparative Example 11 and Examples 199 to 207, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 15. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1118] Table 15

[1119]

[1120]

[1121] As shown in Table 15, compared with the OLED of Ref11 (where the red EML includes compound RD11 as a dopant and CBP as the host), the OLEDs of Ex199 to Ex207 (where the red EML includes compound RD11 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1122] 23. Comparative Example 12 (Ref 12)

[1123] Compound RD12 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form the EML.

[1124] 24. Example

[1125] (1) Examples 208 to 210 (Ex208 to Ex210)

[1126] Compound RD12 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1127] (2) Examples 211 to 213 (Ex211 to Ex213)

[1128] Compound RD12 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1129] (3) Examples 214 to 216 (Ex214 to Ex216)

[1130] Compound RD12 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1131] The characteristics of the OLEDs manufactured in Comparative Example 12 and Examples 208 to 216, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 16. The characteristics of the OLEDs were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1132] Table 16

[1133]

[1134] As shown in Table 16, compared with the OLED of Ref12 (where the red EML includes compound RD12 as a dopant and CBP as the host), the OLEDs of Ex208 to Ex216 (where the red EML includes compound RD12 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1135] 25. Comparative Example 13 (Ref 13)

[1136] Compound RD13 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form the EML.

[1137] 26. Example

[1138] (1) Examples 217 to 219 (Ex217 to Ex219)

[1139] Compound RD13 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1140] (2) Examples 220 to 222 (Ex220 to Ex222)

[1141] Compound RD13 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1142] (3) Examples 223 to 225 (Ex223 to Ex225)

[1143] Compound RD13 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1144] The characteristics of the OLEDs manufactured in Comparative Example 13 and Examples 217 to 225, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 17. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1145] Table 17

[1146]

[1147] As shown in Table 17, compared with the OLED of Ref13 (where the red EML includes compound RD13 as a dopant and CBP as the host), the OLEDs of Ex217 to Ex225 (where the red EML includes compound RD13 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1148] 27. Comparative Example 14 (Ref 14)

[1149] Compound RD14 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form the EML.

[1150] 28. Example

[1151] (1) Examples 226 to 228 (Ex226 to Ex228)

[1152] Compound RD14 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1153] (2) Examples 229 to 231 (Ex229 to Ex231)

[1154] Compound RD14 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1155] (3) Examples 232 to 234 (Ex232 to Ex234)

[1156] Compound RD14 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1157] The characteristics of the OLEDs manufactured in Comparative Example 14 and Examples 226 to 234, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 18. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1158] Table 18

[1159]

[1160]

[1161] As shown in Table 18, compared with the OLED of Ref14 (where the red EML includes compound RD14 as a dopant and CBP as the host), the OLEDs of Ex226 to Ex234 (where the red EML includes compound RD14 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1162] 29. Comparative Example 15 (Ref 15)

[1163] Compound RD15 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form the EML.

[1164] 30. Example

[1165] (1) Examples 235 to 237 (Ex235 to Ex237)

[1166] Compound RD15 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1167] (2) Examples 238 to 240 (Ex238 to Ex240)

[1168] Compound RD15 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1169] (3) Examples 241 to 243 (Ex241 to Ex243)

[1170] Compound RD15 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1171] The characteristics of the OLEDs manufactured in Comparative Example 15 and Examples 235 to 243, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 19. The characteristics of the OLEDs were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1172] Table 19

[1173]

[1174] As shown in Table 19, compared with the OLED of Ref15 (where the red EML includes compound RD15 as a dopant and CBP as the host), the OLEDs of Ex235 to Ex243 (where the red EML includes compound RD15 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1175] 31. Comparative Example 16 (Ref 16)

[1176] Compound RD16 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form the EML.

[1177] 32. Example

[1178] (1) Examples 244 to 246 (Ex244 to Ex246)

[1179] Compound RD16 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1180] (2) Examples 247 to 249 (Ex247 to Ex249)

[1181] Compound RD16 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1182] (3) Examples 250 to 252 (Ex250 to Ex252)

[1183] Compound RD16 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1184] The characteristics of the OLEDs manufactured in Comparative Example 16 and Examples 244 to 252, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 20. The characteristics of the OLEDs were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1185] Table 20

[1186]

[1187] As shown in Table 20, compared with the OLED of Ref16 (where the red EML includes compound RD16 as a dopant and CBP as the host), the OLEDs of Ex244 to Ex252 (where the red EML includes compound RD16 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1188] 33. Comparative Example 17 (Ref 17)

[1189] Compound RD17 from Formula 8 was used as a dopant and compound (CBP) from Formula 7 was used as the host to form the EML.

[1190] 34. Example

[1191] (1) Examples 253 and 255 (Ex253 and Ex255)

[1192] Compound RD17 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1193] (2) Examples 256 and 258 (Ex256 and Ex258)

[1194] Compound RD17 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1195] (3) Examples 259 and 261 (Ex259 and Ex261)

[1196] Compound RD17 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1197] The characteristics of the OLEDs manufactured in Comparative Example 17 and Examples 253 to 261, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 21. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1198] Table 21

[1199]

[1200]

[1201] As shown in Table 21, compared with the OLED of Ref17 (where the red EML includes compound RD17 as a dopant and CBP as the host), the OLEDs of Ex253 to Ex261 (where the red EML includes compound RD17 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1202] 35. Comparative Example 18 (Ref 18)

[1203] Compound RD18 from Formula 8 was used as a dopant and compound (CBP) from Formula 7 was used as the host to form an EML.

[1204] 36. Example

[1205] (1) Examples 262 and 264 (Ex262 and Ex264)

[1206] Compound RD18 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1207] (2) Examples 265 and 267 (Ex265 and Ex267)

[1208] Compound RD18 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1209] (3) Examples 268 and 270 (Ex268 and Ex270)

[1210] Compound RD18 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1211] The characteristics of the OLEDs manufactured in Comparative Example 18 and Examples 262 to 270, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 22. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1212] Table 22

[1213]

[1214] As shown in Table 22, compared with the OLED of Ref18 (where the red EML includes compound RD21 as a dopant and CBP as the host), the OLEDs of Ex262 to Ex270 (where the red EML includes compound RD18 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1215] 37. Comparative Example 19 (Ref 19)

[1216] Compound RD19 from Formula 8 was used as a dopant and compound (CBP) from Formula 7 was used as the host to form the EML.

[1217] 38. Example

[1218] (1) Examples 271 and 273 (Ex271 and Ex273)

[1219] Compound RD19 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1220] (2) Examples 274 and 276 (Ex274 and Ex276)

[1221] Compound RD19 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1222] (3) Examples 277 and 279 (Ex277 and Ex279)

[1223] Compound RD19 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1224] The characteristics of the OLEDs manufactured in Comparative Example 19 and Examples 271 to 279, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 23. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1225] Table 23

[1226]

[1227] As shown in Table 23, compared with the OLED of Ref19 (where the red EML includes compound RD19 as a dopant and CBP as the host), the OLEDs of Ex271 to Ex279 (where the red EML includes compound RD19 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1228] 39. Comparative Example 20 (Ref 20)

[1229] Compound RD20 from Formula 8 was used as a dopant and compound (CBP) from Formula 7 was used as the host to form an EML.

[1230] 40. Example

[1231] (1) Examples 280 and 282 (Ex280 and Ex282)

[1232] Compound RD20 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1233] (2) Examples 283 and 285 (Ex283 and Ex285)

[1234] Compound RD20 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1235] (3) Examples 286 and 288 (Ex286 and Ex288)

[1236] Compound RD20 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1237] The characteristics of the OLEDs manufactured in Comparative Example 20 and Examples 280 to 288, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 24. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1238] Table 24

[1239]

[1240]

[1241] As shown in Table 24, compared with the OLED of Ref20 (where the red EML includes compound RD20 as a dopant and CBP as the host), the OLEDs of Ex280 to Ex288 (where the red EML includes compound RD20 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1242] 41. Comparative Example 21 (Ref 21)

[1243] Compound RD21 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form an EML.

[1244] 42. Example

[1245] (1) Examples 289 and 291 (Ex289 and Ex291)

[1246] Compound RD21 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1247] (2) Examples 292 and 294 (Ex292 and Ex294)

[1248] Compound RD21 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1249] (3) Examples 295 and 297 (Ex295 and Ex297)

[1250] Compound RD21 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1251] The characteristics of the OLEDs manufactured in Comparative Example 21 and Examples 289 to 297, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 25. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1252] Table 25

[1253]

[1254] As shown in Table 25, compared with the OLED of Ref21 (where the red EML includes compound RD21 as a dopant and CBP as the host), the OLEDs of Ex289 to Ex297 (where the red EML includes compound RD21 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1255] 43. Comparative Example 22 (Ref 22)

[1256] Compound RD22 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form an EML.

[1257] 44. Example

[1258] (1) Examples 298 and 300 (Ex298 and Ex300)

[1259] Compound RD22 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1260] (2) Examples 301 and 303 (Ex301 and Ex303)

[1261] Compound RD22 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1262] (3) Examples 304 and 306 (Ex304 and Ex306)

[1263] Compound RD22 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1264] The characteristics of the OLEDs manufactured in Comparative Example 22 and Examples 298 to 306, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 26. The characteristics of the OLEDs were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1265] Table 26

[1266]

[1267] As shown in Table 26, compared with the OLED of Ref22 (where the red EML includes compound RD22 as a dopant and CBP as the host), the OLEDs of Ex298 to Ex306 (where the red EML includes compound RD22 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1268] 45. Comparative Example 23 (Ref 23)

[1269] Compound RD23 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form an EML.

[1270] 46. ​​Example

[1271] (1) Examples 307 and 309 (Ex307 and Ex309)

[1272] Compound RD23 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1273] (2) Examples 310 and 312 (Ex310 and Ex312)

[1274] Compound RD23 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1275] (3) Examples 313 and 315 (Ex313 and Ex315)

[1276] Compound RD23 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1277] The characteristics of the OLEDs manufactured in Comparative Example 23 and Examples 307 to 315, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 27. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1278] Table 27

[1279]

[1280]

[1281] As shown in Table 27, compared with the OLED of Ref20 (where the red EML includes compound RD23 as a dopant and CBP as the host), the OLEDs of Ex307 to Ex315 (where the red EML includes compound RD23 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1282] 47. Comparative Example 24 (Ref 24)

[1283] Compound RD24 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form an EML.

[1284] 48. Example

[1285] (1) Examples 316 and 318 (Ex316 and Ex318)

[1286] Compound RD24 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1287] (2) Examples 319 and 321 (Ex319 and Ex321)

[1288] Compound RD24 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1289] (3) Examples 322 and 324 (Ex322 and Ex324)

[1290] Compound RD24 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1291] The characteristics of the OLEDs manufactured in Comparative Example 24 and Examples 316 to 324, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 28. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1292] Table 28

[1293]

[1294] As shown in Table 28, compared with the OLED of Ref24 (where the red EML includes compound RD24 as a dopant and CBP as the host), the OLEDs of Ex316 to Ex324 (where the red EML includes compound RD24 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1295] 49. Comparative Example 25 (Ref 25)

[1296] Compound RD25 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form an EML.

[1297] 50. Example

[1298] (1) Examples 325 and 327 (Ex325 and Ex327)

[1299] Compound RD25 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1300] (2) Examples 328 and 330 (Ex328 and Ex330)

[1301] Compound RD25 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1302] (3) Examples 331 and 333 (Ex331 and Ex333)

[1303] Compound RD25 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1304] The characteristics of the OLEDs manufactured in Comparative Example 25 and Examples 325 to 333, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 29. The characteristics of the OLEDs were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1305] Table 29

[1306]

[1307] As shown in Table 29, compared with the OLED of Ref25 (where the red EML includes compound RD25 as a dopant and CBP as the host), the OLEDs of Ex325 to Ex333 (where the red EML includes compound RD25 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1308] 51. Comparative Example 26 (Ref 26)

[1309] Compound RD26 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form an EML.

[1310] 52. Example

[1311] (1) Examples 334 and 336 (Ex334 and Ex336)

[1312] Compound RD26 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1313] (2) Examples 337 and 339 (Ex337 and Ex339)

[1314] Compound RD26 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1315] (3) Examples 340 and 342 (Ex340 and Ex342)

[1316] Compound RD26 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1317] The characteristics of the OLEDs manufactured in Comparative Example 26 and Examples 334 to 342, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 30. The characteristics of the OLEDs were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1318] Table 30

[1319]

[1320]

[1321] As shown in Table 30, compared with the OLED of Ref26 (where the red EML includes compound RD26 as a dopant and CBP as the host), the OLEDs of Ex334 to Ex342 (where the red EML includes compound RD26 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1322] 53. Comparative Example 27 (Ref 27)

[1323] Compound RD27 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form an EML.

[1324] 54. Examples

[1325] (1) Examples 343 and 345 (Ex342 and Ex345)

[1326] Compound RD27 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1327] (2) Examples 346 and 348 (Ex346 and Ex348)

[1328] Compound RD27 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1329] (3) Examples 349 and 351 (Ex349 and Ex351)

[1330] Compound RD27 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1331] The characteristics of the OLEDs manufactured in Comparative Example 27 and Examples 343 to 351, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 31. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1332] Table 31

[1333]

[1334] As shown in Table 31, compared with the OLED of Ref27 (where the red EML includes compound RD27 as a dopant and CBP as the host), the OLEDs of Ex343 to Ex351 (where the red EML includes compound RD27 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1335] 55. Comparative Example 28 (Ref 28)

[1336] Compound RD28 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form an EML.

[1337] 56. Example

[1338] (1) Examples 352 and 354 (Ex352 and Ex354)

[1339] Compound RD28 from Formula 8 was used as a dopant, compound RHH-5 from Formula 2-4 as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1340] (2) Examples 355 and 357 (Ex355 and Ex357)

[1341] Compound RD28 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1342] (3) Examples 358 and 360 (Ex358 and Ex360)

[1343] Compound RD28 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1344] The characteristics of the OLEDs manufactured in Comparative Example 28 and Examples 352 to 360, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 32. The OLED characteristics were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1345] Table 32

[1346]

[1347] As shown in Table 32, compared with the Ref28 OLED (where the red EML includes compound RD28 as a dopant and CBP as the host), the Ex352 to Ex360 OLEDs (where the red EML includes compound RD28 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1348] 57. Comparative Example 29 (Ref 29)

[1349] Compound RD29 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form an EML.

[1350] 58. Examples

[1351] (1) Examples 361 and 363 (Ex361 and Ex363)

[1352] Compound RD29 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1353] (2) Examples 364 and 366 (Ex364 and Ex366)

[1354] Compound RD29 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1355] (3) Examples 367 and 369 (Ex367 and Ex369)

[1356] Compound RD29 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1357] The characteristics of the OLEDs manufactured in Comparative Example 29 and Examples 361 to 369, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 33. The characteristics of the OLEDs were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1358] Table 33

[1359]

[1360]

[1361] As shown in Table 33, compared with the OLED of Ref29 (where the red EML includes compound RD29 as a dopant and CBP as the host), the OLEDs of Ex361 to Ex369 (where the red EML includes compound RD29 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1362] 59. Comparative Example 30 (Ref 30)

[1363] Compound RD30 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form an EML.

[1364] 60. Example

[1365] (1) Examples 370 and 372 (Ex370 and Ex372)

[1366] Compound RD30 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1367] (2) Examples 373 and 375 (Ex373 and Ex375)

[1368] Compound RD30 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1369] (3) Examples 376 and 378 (Ex376 and Ex378)

[1370] Compound RD30 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1371] The characteristics of the OLEDs manufactured in Comparative Example 30 and Examples 370 to 378, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 34. The characteristics of the OLEDs were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1372] Table 34

[1373]

[1374] As shown in Table 34, compared with the OLED of Ref30 (where the red EML includes compound RD30 as a dopant and CBP as the host), the OLEDs of Ex370 to Ex378 (where the red EML includes compound RD30 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1375] 61. Comparative Example 31 (Ref 31)

[1376] Compound RD31 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form an EML.

[1377] 62. Example

[1378] (1) Examples 379 and 381 (Ex379 and Ex381)

[1379] Compound RD31 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1380] (2) Examples 382 and 384 (Ex382 and Ex384)

[1381] Compound RD31 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1382] (3) Examples 385 and 387 (Ex385 and Ex387)

[1383] Compound RD31 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1384] The characteristics of the OLEDs manufactured in Comparative Example 31 and Examples 379 to 387, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 35. The characteristics of the OLEDs were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1385] Table 35

[1386]

[1387] As shown in Table 35, compared with the OLED of Ref31 (where the red EML includes compound RD31 as a dopant and CBP as the host), the OLEDs of Ex379 to Ex387 (where the red EML includes compound RD31 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1388] 63. Comparative Example 32 (Ref 32)

[1389] Compound RD32 from Formula 8 and compound (CBP) from Formula 7 were used as dopant and host, respectively, to form an EML.

[1390] 64. Example

[1391] (1) Examples 388 and 390 (Ex388 and Ex390)

[1392] Compound RD32 from Formula 8 is used as a dopant, compound RHH-5 from Formula 2-4 is used as the first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1393] (2) Examples 391 and 393 (Ex391 and Ex393)

[1394] Compound RD32 from Formula 8 is used as a dopant, compound RHH-11 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1395] (3) Examples 394 and 396 (Ex394 and Ex396)

[1396] Compound RD32 from Formula 8 is used as a dopant, compound RHH-22 from Formula 2-4 is used as a first host, and compounds REH-1, REH-12, and REH-30 from Formula 3-4 are used as second dopant to form an EML. (First host: Second host = 1:1 (wt%))

[1397] The characteristics of the OLEDs manufactured in Comparative Example 32 and Examples 388 to 396, namely driving voltage (V), external quantum efficiency (EQE), and lifetime (LT95), were measured and are listed in Table 36. The characteristics of the OLEDs were measured at room temperature using a current source (KEITHLEY) and a photometer (PR 650). The current density was 10 mA / cm². 2 The driving voltage and external quantum efficiency were measured under the conditions of 40 °C and 40 mA / cm². 2 The lifespan (time to reach 95% of the lifespan) is measured under certain conditions.

[1398] Table 36

[1399]

[1400]

[1401] As shown in Table 36, compared with the OLED of Ref32 (where the red EML includes compound RD32 as a dopant and CBP as the host), the OLEDs of Ex388 to Ex396 (where the red EML includes compound RD32 as a dopant, compounds RHH-5, RHH-11 and RHH-22 as the first host, and compounds REH-1, REH-12 and REH-30 as the second host) have advantages in driving voltage, luminous efficiency and luminous lifetime.

[1402] It will be apparent to those skilled in the art that various modifications and variations can be made to the invention without departing from its scope. Therefore, this invention is intended to cover such modifications and variations as long as they fall within the scope of the appended claims.

Claims

1. An organic light-emitting diode, comprising: First electrode; The second electrode facing the first electrode; and The first light-emitting part includes a first red light-emitting material layer and is located between the first electrode and the second electrode. The first red luminescent material layer comprises a first compound, a second compound, and a third compound. The first compound is one of the compounds in Formula 1: [Formula 1] The second compound is represented by formula 2: [Equation 2] The third compound is represented by formula 3-1: [Equation 3-1] in M is an oxygen atom (O) or a sulfur atom (S); Q and Z are each independently selected from unsubstituted or substituted C6-C, whether deuterated or undeuterated. 30 Aryl and deuterated or undeuterated unsubstituted or substituted C3-C 30 Group composed of heteroaryl groups; L 2 Choose C6-C, either unsubstituted or substituted. 30 aryl and unsubstituted or substituted C3-C 30 The group composed of heteroarylene groups, and b is 0 or 1.

2. The organic light-emitting diode according to claim 1, wherein formula 3-1 is represented by formula 3-2: [Equation 3-2] In Equation 3-2, M, Q, Z, and L 2 b is defined in the same way as in Equation 3-1.

3. The organic light-emitting diode as described in claim 1, wherein formula 3-1 is represented by formula 3-3: [Equation 3-3] In Equation 3-3, M, Q, Z, and L 2 b is defined in the same way as in Equation 3-1.

4. The organic light-emitting diode according to claim 1, wherein the third compound is one of the compounds in formulas 3-4: [Equation 3-4] 5. The organic light-emitting diode according to claim 1, wherein the weight percentage of the second compound and the third compound is each greater than the weight percentage of the first compound.

6. The organic light-emitting diode according to claim 1, further comprising: The second light-emitting part includes a second red light-emitting material layer and is located between the first light-emitting part and the second electrode; and A charge-generating layer is located between the first and second light-emitting portions.

7. The organic light-emitting diode according to claim 6, wherein, The second red luminescent material layer includes a fourth compound represented by Formula 1-1, a fifth compound represented by Formula 2-1, and a sixth compound represented by Formula 3-1.

8. The organic light-emitting diode according to claim 1, further comprising: The second light-emitting part includes a first blue light-emitting material layer and is located between the first electrode and the first light-emitting part; and A first charge-generating layer is located between the first and second light-emitting portions.

9. The organic light-emitting diode according to claim 8, further comprising: The third light-emitting part includes a second blue light-emitting material layer and is located between the first light-emitting part and the second electrode; and The second charge-generating layer is located between the first and third light-emitting parts.

10. The organic light-emitting diode according to claim 9, wherein, The first light-emitting part further includes a green light-emitting material layer located between the red light-emitting material layer and the second charge-generating layer.

11. The organic light-emitting diode according to claim 10, wherein, The first light-emitting part further includes a yellow-green light-emitting material layer located between the red light-emitting material layer and the green light-emitting material layer.

12. An organic light-emitting device, comprising: Substrate; The organic light-emitting diode according to claim 1 is located on the substrate.

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