organic light-emitting devices

Abstract

The present disclosure relates to an organic light-emitting device (OLED). In particular, the present disclosure relates to an organic light-emitting diode (OLED) and an organic light-emitting device (OLED), each comprising: at least one luminescent material layer comprising a boron-based dopant and an anthracene-based host substituted with at least one deuterium; at least one electron-blocking layer comprising an amine-based compound substituted with at least one spiroaryl group; and optionally, at least one hole-blocking layer comprising an azine-based or benzimidazole-based compound. These OLEDs and OLEDs exhibit improved luminous efficiency and enhanced luminous lifetime.

Description

[0001] This application claims priority to Korean Patent Application No. 10-2020-0184940 filed in the Republic of Korea on December 28, 2020, the entire contents of which are hereby expressly incorporated by reference into this application in their entirety. Technical Field

[0002] The present disclosure relates to an organic light-emitting device, and more particularly, to an organic light-emitting device having excellent luminous efficiency and luminous lifetime. Background Art

[0003] Among the widely used flat panel display devices, organic light emitting diodes (OLEDs) have become a focus as display devices that are rapidly replacing liquid crystal displays (LCDs). OLEDs can form smaller than OLEDs are made of thin organic films and can achieve unidirectional or bidirectional images through electrode arrangement. Furthermore, OLEDs can even be formed on flexible, transparent substrates such as plastic substrates, making it easy to realize flexible or foldable display devices. Furthermore, compared to LCDs, OLEDs can be driven at lower voltages and exhibit exceptionally high color purity.

[0004] Because fluorescent materials only utilize singlet exciton energy during luminescence, existing fluorescent materials exhibit low luminescence efficiency. In contrast, phosphorescent materials can exhibit high luminescence efficiency because they utilize both triplet and singlet exciton energy during luminescence. However, metal complexes, which are representative phosphorescent materials, have a very short luminescence lifetime in commercial applications. In particular, blue-emitting materials do not exhibit satisfactory luminescence efficiency and luminescence lifetime compared to luminescent materials of other colors. Therefore, there is a need to develop new compounds or device structures that can improve the luminescence efficiency and luminescence lifetime of organic light-emitting diodes. Summary of the Invention

[0005] Accordingly, embodiments of the present disclosure are directed to an organic light emitting device that substantially obviates one or more problems due to limitations and disadvantages of the related art.

[0006] An aspect of the present disclosure is to provide an organic light emitting device having improved luminous efficiency and luminous lifetime.

[0007] Other features and aspects will be described in the following description and, in part, will be apparent from the description or may be learned by practicing the inventive concepts provided herein. Other features and aspects of the inventive concepts may be realized and achieved by the structures particularly pointed out in the written description, or structures derivable therefrom, as well as the claims and drawings of the present invention.

[0008] To achieve these and other aspects of the inventive concept as embodied and generally described, an organic light-emitting device includes: a substrate; and an organic light-emitting diode on the substrate, the organic light-emitting diode including a first electrode, a second electrode facing the first electrode, and a light-emitting layer arranged between the first electrode and the second electrode, wherein the light-emitting layer includes: a first light-emitting material layer including a first dopant and a first host, and a first electron blocking layer arranged between the first electrode and the first light-emitting material layer, wherein the first dopant includes a boron compound having a structure of the following Formula 1A or Formula 1B, wherein the first host includes an anthracene compound having a structure of the following Formula 3, and wherein the first electron blocking layer includes an amine compound having a structure of the following Formula 5.

[0009] [Formula 1A]

[0010]

[0011] Among them, R 11 to R 14 and R 21 to R 24 Each independently selected from hydrogen, C1-C 10 Alkyl, C6-C 30 Aryl, C6-C 30 Arylamino, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups, or R 11 to R 14 and R 21 to R 24 The two adjacent ones form a fused ring, where R 11 to R 14 and R 21 to R 24 The aryl, arylamino, heteroaryl and alicyclic groups are each independently free of substituents or substituted with at least one C1-C 10 Alkyl; R 31 and R 41 Each independently selected from hydrogen, C1-C 10 Alkyl, C6-C 30 Aryl, C6-C 30 Arylamino, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups, wherein R 31 and R 41 The aryl, arylamino, heteroaryl and alicyclic groups are each independently free of substituents or substituted with at least one C1-C 10 Alkyl; R 51 Selected from hydrogen, C1-C 10 Alkyl, C3-C 15Cycloalkyl, C6-C 30 Aryl, C6-C 30 Arylamino, C5-C 30 Heteroaryl, C3-C 30 Alicyclic and C5-C 30 A group consisting of heterocyclic groups, wherein R 51 The cycloalkyl, aryl, arylamino, heteroaryl, alicyclic and heterocyclic groups are each independently free of substituents or substituted with at least one C1-C 10 Alkyl; when R 31 、R 41 and R 51 Each is substituted with at least one C1-C 10 Alkyl C6-C 30 In the case of an aryl group, the substituted alkyl groups are linked to each other to form a fused ring;

[0012] [Formula 1B]

[0013]

[0014] wherein X is NR1, CR2R3, O, S, Se or SiR4R5, and R1 to R5 are each independently selected from hydrogen, C1-C 10 Alkyl, C6-C 30 Aryl, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups; R 61 to R 64 Each independently selected from hydrogen, C1-C 10 Alkyl, C6-C 30 Aryl, C6-C 30 Arylamino, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups, or R 61 to R 64 The two adjacent ones form a fused ring, where R 61 to R 64 The aryl, arylamino, heteroaryl and alicyclic groups are each independently free of substituents or substituted with at least one C1-C 10 Alkyl; R 71 to R 74 Each independently selected from hydrogen, C1-C 10 Alkyl and C3-C 30 A group consisting of alicyclic groups; R 81 Choose from C6-C 30 Aryl, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups, or R 81 and R 61Form a fused ring, where R 81 The aryl, heteroaryl and alicyclic groups are each independently free of substituents or substituted with at least one C1-C 10 Alkyl; R 82 Choose from C6-C 30 Aryl, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups, wherein R 82 The aryl, heteroaryl and alicyclic groups are each independently free of substituents or substituted with at least one C1-C 10 Alkyl; R 91 Selected from hydrogen, C1-C 10 Alkyl, C3-C 15 Cycloalkyl, C6-C 30 Aryl, C6-C 30 Arylamino, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups, wherein R 91 The cycloalkyl, aryl, arylamino, heteroaryl and alicyclic groups are each independently unsubstituted or substituted with at least one C1-C 10 Alkyl; when R 81 、R 82 and R 91 Each is substituted with at least one C1-C 10 Alkyl C6-C 30 In the case of an aryl group, the substituted alkyl groups are linked to each other to form a fused ring;

[0015] [Formula 3]

[0016]

[0017] wherein Ar1 and Ar2 are each independently C6-C 30 Aryl or C5-C 30 Heteroaryl; L is a single bond, C6-C 20 Arylene or C5-C 20 heteroarylene; a is an integer from 0 to 8; b, c and d are each independently an integer from 0 to 30, wherein at least one of a, b, c and d is a positive integer;

[0018] [Formula 5]

[0019]

[0020] Among them, L3 is C6-C 30 Arylene; o is 0 or 1; R 121 and R 122 Each independently is C6-C 30 Aryl or C5-C 30Heteroaryl, wherein the C6-C 30 Aryl or the C5-C 30 Heteroaryl groups are each optionally substituted with C1-C 10 Alkyl and C6-C 30 At least one of the aryl groups.

[0021] As an example, R in Formula 1A 11 to R 14 、R 21 to R 24 、R 31 and R 41 Each can be independently selected from hydrogen, C1-C 10 Alkyl, C6-C 30 Aryl and C5-C 30 The group consisting of heteroaryl groups, wherein R 11 to R 14 、R 21 to R 24 、R 31 and R 41 The aryl and heteroaryl groups may each independently be unsubstituted or substituted with C1-C 10 Alkyl, wherein R 51 You can choose from C1-C 10 Alkyl, C6-C 30 Arylamino, C5-C 30 Heteroaryl and C3-C 30 A group consisting of a heterocyclic group, and wherein R 51 The heteroaryl, arylamino and heterocyclic groups may each independently be unsubstituted or substituted with C1-C 10 alkyl.

[0022] Alternatively, X of Formula 1B may be O or S, wherein R 61 to R 64 Each can be independently selected from hydrogen, C1-C 10 Alkyl and C6-C 30 A group consisting of an arylamino group, or R 61 to R 64 Two adjacent rings can form a fused ring, where R 71 to R 74 Each can be independently selected from hydrogen and C1-C 10 A group consisting of alkyl groups, wherein R 81 You can choose from C6-C 30 Aryl and C5-C 30 A group consisting of heteroaryl groups, or R 81 and R 61 Can form a fused ring, where R 81The aryl and heteroaryl groups may each independently be unsubstituted or substituted with C1-C 10 Alkyl, where R 82 You can choose from C6-C 30 Aryl and C5-C 30 The group consisting of heteroaryl groups, wherein R 82 The aryl and heteroaryl groups may each independently be unsubstituted or substituted with C1-C 10 alkyl, and wherein R 91 Can be C1-C 10 alkyl.

[0023] The light emitting layer may further include a first hole blocking layer disposed between the first light emitting material layer and the second electrode.

[0024] As an example, the first hole blocking layer may include at least one of an azine-based compound having a structure of the following Formula 7 and a benzimidazole-based compound having a structure of the following Formula 9:

[0025] [Formula 7]

[0026]

[0027] wherein Y1 to Y5 are each independently CR 131 or N, one to three of Y1 to Y5 are N, and R 131 It is C6-C 30 Aryl; L is C6-C 30 Arylene; R 132 It is C6-C 30 Aryl or C5-C 30 Heteroaryl, wherein C6-C 30 Aryl is optionally substituted with another C6-C 30 Aryl or C5-C 30 Heteroaryl, or with C 10 -C 30 Fused aryl ring or C 10 -C 30 The fused heteroaryl ring forms a spirocyclic structure wherein the other C6-C 30 The aryl group may be further substituted with other C6-C 30 Aryl or C5-C 30 Heteroaryl, or with C 10 -C 30 The fused aromatic rings form a spiro ring structure; R 133 is hydrogen, or two adjacent R 133 forming a fused aromatic ring; r is 0 or 1; s is 1 or 2; and t is an integer from 0 to 4;

[0028] [Formula 9]

[0029]

[0030] Where Ar is C 10 -C 30 Arylene; R 141 It is C6-C 30 Aryl or C5-C 30 Heteroaryl, C6-C 30 Aryl and C5-C 30 The heteroaryl groups are each optionally substituted with C1-C 10 alkyl; and R 142 and R 143 are independently hydrogen, C1-C 10 Alkyl or C6-C 30 Aryl.

[0031] Alternatively, the light emitting layer may further include a second light emitting material layer disposed between the first light emitting material layer and the second electrode, and a first charge generation layer disposed between the first and second light emitting material layers.

[0032] The second light emitting material layer may include a second dopant and a second host, wherein the second dopant may include a boron-based compound having a structure of Formula 1A or Formula 1B, and the second host may include an anthracene-based compound having a structure of Formula 3.

[0033] In addition, the light emitting layer may further include a second electron blocking layer disposed between the first charge generation layer and the second light emitting material layer, wherein the second electron blocking layer may include an amine compound having a structure of Formula 5.

[0034] The light emitting layer may further include at least one of a first hole blocking layer disposed between the first light emitting material layer and the first charge generation layer and a second hole blocking layer disposed between the second light emitting material layer and the second electrode.

[0035] For example, the light emitting layer may further include a third light emitting material layer disposed between the second light emitting material layer and the second electrode and a second charge generation layer disposed between the second and third light emitting material layers.

[0036] The substrate may define a red pixel region, a green pixel region, and a blue pixel region, and the organic light-emitting diodes may be correspondingly located in the red pixel region, the green pixel region, and the blue pixel region, and the organic light-emitting device may further include a color conversion layer corresponding to the red pixel region and the green pixel region arranged between the substrate and the organic light-emitting diodes or arranged above the organic light-emitting diodes.

[0037] In one exemplary aspect, the second light emitting material layer can emit yellow-green (YG) light or red-green (RG) light.

[0038] In this case, the substrate may define a red pixel region, a green pixel region, and a blue pixel region, and the organic light-emitting diodes may be located correspondingly in the red pixel region, the green pixel region, and the blue pixel region, and the organic light-emitting device may further include a color filter layer corresponding to the red pixel region, the green pixel region, and the blue pixel region arranged between the substrate and the organic light-emitting diode or arranged above the organic light-emitting diode.

[0039] It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory and are intended to provide further explanation of the inventive concept as claimed. BRIEF DESCRIPTION OF THE DRAWINGS

[0040] The accompanying drawings, which are included to provide a further understanding of the disclosure and are incorporated in and constitute a part of this application, illustrate embodiments of the disclosure and together with the description serve to explain the principle of the disclosure.

[0041] Figure 1 is a schematic circuit diagram illustrating an organic light emitting display device of the present disclosure.

[0042] Figure 2 is a cross-sectional view illustrating an organic light-emitting display device as an example of an organic light-emitting device according to an exemplary aspect of the present disclosure.

[0043] Figure 3 is a cross-sectional view illustrating an organic light emitting diode having a single light emitting portion according to an exemplary aspect of the present disclosure.

[0044] Figure 4 is a cross-sectional view illustrating an organic light emitting diode having a double stack structure according to another exemplary aspect of the present disclosure.

[0045] Figure 5 is a cross-sectional view illustrating an organic light emitting display device according to another exemplary aspect of the present disclosure.

[0046] Figure 6 is a cross-sectional view illustrating an organic light emitting diode having a double stack structure according to still another exemplary aspect of the present disclosure.

[0047] Figure 7 is a cross-sectional view illustrating an organic light emitting diode having a triple-stack structure according to still another exemplary aspect of the present disclosure.

[0048] Figure 8 is a cross-sectional view illustrating an organic light emitting display device according to still another exemplary aspect of the present disclosure. DETAILED DESCRIPTION

[0049] Reference will now be made in detail to various aspects of the present disclosure, examples of which are illustrated in the accompanying drawings.

[0050] The organic light-emitting diode disclosed herein can improve its luminous efficiency and luminous lifetime by applying specific organic compounds to the luminescent material layer, electron blocking layer, and / or hole blocking layer. The organic light-emitting diode can be applied to organic light-emitting devices, such as organic light-emitting display devices or organic light-emitting lighting devices.

[0051] Figure 1 FIG. 1 is a circuit diagram illustrating the organic light emitting display device disclosed herein. Figure 1 As shown, in an organic light-emitting display device, gate lines GL, data lines DL, and power lines PL are formed, intersecting each other to define pixel regions P. A switching thin-film transistor Ts, a driving thin-film transistor Td, a storage capacitor Cst, and an organic light-emitting diode D are formed in the pixel region P. The pixel region P may include a red (R) pixel region, a green (G) pixel region, and a blue (B) pixel region.

[0052] The switching thin-film transistor Ts is connected to the gate line GL and the data line DL. The driving thin-film transistor Td and the storage capacitor Cst are connected between the switching thin-film transistor Ts and the power line PL. The organic light-emitting diode D is connected to the driving thin-film transistor Td. When the switching thin-film transistor Ts is turned on by a gate signal applied to the gate line GL, the data signal applied to the data line DL is applied to the gate electrode of the driving thin-film transistor Td and one electrode of the storage capacitor Cst via the switching thin-film transistor Ts.

[0053] The driving thin-film transistor Td is turned on by a data signal applied to its gate electrode, allowing a current proportional to the data signal to flow from the power line PL through the driving thin-film transistor Td to the organic light-emitting diode D. The organic light-emitting diode D then emits light with a brightness proportional to the current flowing through the driving thin-film transistor Td. In this state, the storage capacitor Cst is charged with a voltage proportional to the data signal, thereby maintaining a constant voltage at the gate electrode of the driving thin-film transistor Td during one frame. As a result, the organic light-emitting display device can display a desired image.

[0054] Figure 2 1 is a cross-sectional view of an organic light emitting display device depicting an exemplary aspect of the present disclosure. Figure 2 As shown, the organic light-emitting display device 100 includes a substrate 102, a thin-film transistor Tr on the substrate 102, and an organic light-emitting diode D connected to the thin-film transistor Tr. As an example, the substrate 102 defines a red pixel region, a green pixel region, and a blue pixel region, and an organic light-emitting diode D is located in each pixel region. In other words, the organic light-emitting diode D, which emits red, green, or blue (B) light, is located in the red pixel region, the green pixel region, and the blue pixel region, respectively.

[0055] The substrate 102 may include, but is not limited to, glass, a thin flexible material, and / or a polymer plastic. For example, the flexible material may be selected from, but is not limited to, polyimide (PI), polyethersulfone (PES), polyethylene naphthalate (PEN), polyethylene terephthalate (PET), polycarbonate (PC), and combinations thereof. The substrate 102 on which the thin film transistors Tr and the organic light emitting diodes D are arranged forms an array substrate.

[0056] The buffer layer 106 may be disposed on the substrate 102, and the thin film transistor Tr is disposed on the buffer layer 106. The buffer layer 106 may be omitted.

[0057] A semiconductor layer 110 is disposed on the buffer layer 106. In one exemplary aspect, the semiconductor layer 110 may include, but is not limited to, an oxide semiconductor material. In this case, a light shielding pattern may be disposed below the semiconductor layer 110 to prevent light from entering the semiconductor layer 110, thereby preventing the semiconductor layer 110 from being degraded by the light. Alternatively, the semiconductor layer 110 may include polycrystalline silicon. In this case, impurities may be doped at the opposite edges of the semiconductor layer 110.

[0058] The gate insulating layer 120 including an insulating material is disposed on the semiconductor layer 110. The gate insulating layer 120 may include, but is not limited to, an inorganic insulating material such as silicon oxide (SiO x ) or silicon nitride (SiN x ).

[0059] The gate electrode 130 made of a conductive material such as metal is disposed on the gate insulating layer 120 so as to correspond to the center of the semiconductor layer 110. Figure 2 The gate insulating layer 120 is disposed on the entire area of ​​the substrate 102 , but the gate insulating layer 120 may be patterned identically to the gate 130 .

[0060] An interlayer insulating layer 140 including an insulating material is disposed on the gate 130, covering the entire surface of the substrate 102. The interlayer insulating layer 140 may include an inorganic insulating material, such as silicon oxide (SiO x ) or silicon nitride (SiN x ), or organic insulating materials such as benzocyclobutene or photo-acryl.

[0061] The interlayer insulating layer 140 has a first semiconductor layer contact hole 142 and a second semiconductor layer contact hole 144, exposing both sides of the semiconductor layer 110. The first semiconductor layer contact hole 142 and the second semiconductor layer contact hole 144 are arranged on opposite sides of the gate 130 and are spaced apart from the gate 130. The first semiconductor layer contact hole 142 and the second semiconductor layer contact hole 144 are formed at Figure 2Alternatively, when the gate insulating layer 120 is patterned identically to the gate electrode 130 , the first semiconductor layer contact hole 142 and the second semiconductor layer contact hole 144 are formed only in the interlayer insulating layer 140 .

[0062] A source electrode 152 and a drain electrode 154 are arranged on the interlayer insulating layer 140 and are made of a conductive material such as metal. The source electrode 152 and the drain electrode 154 are separated from each other relative to the gate 130 and contact both sides of the semiconductor layer 110 through the first semiconductor layer contact hole 142 and the second semiconductor layer contact hole 144, respectively.

[0063] The semiconductor layer 110 , the gate electrode 130 , the source electrode 152 , and the drain electrode 154 constitute a thin film transistor Tr, which functions as a driving element. Figure 2 The thin film transistor Tr in FIG has a coplanar structure, wherein the gate 130, the source 152, and the drain 154 are arranged on the semiconductor layer 110. Alternatively, the thin film transistor Tr may have an inversely staggered structure, wherein the gate is arranged under the semiconductor layer and the source and drain are arranged on the semiconductor layer. In this case, the semiconductor layer may include amorphous silicon.

[0064] Although Figure 2 Although not shown, gate lines and data lines that intersect to define the pixel area, as well as switching elements connected to the gate lines and data lines, may be further formed in the pixel area. The switching element is connected to a thin film transistor Tr serving as a driving element. In addition, the power line is parallel to and spaced from the gate line or the data line, and the thin film transistor Tr may further include a storage capacitor configured to constantly maintain the voltage of the electrode during a frame.

[0065] A passivation layer 160 is disposed on the source electrode 152 and the drain electrode 154, and the thin film transistor Tr covers the entire substrate 102. The passivation layer 160 has a flat top surface and a drain contact hole 162 that exposes the drain electrode 154 of the thin film transistor Tr. Although the drain contact hole 162 is disposed on the second semiconductor layer contact hole 144, it can be separated from the second semiconductor layer contact hole 144.

[0066] The organic light emitting diode (OLED) D includes a first electrode 210 disposed on the passivation layer 160 and connected to the drain electrode 154 of the thin film transistor Tr. The organic light emitting diode D further includes a light emitting layer 230 and a second electrode 220, each disposed on the first electrode 210 in sequence.

[0067] The first electrode 210 is arranged in each pixel region. The first electrode 210 can be an anode and includes a conductive material having a relatively high work function value. For example, the first electrode 210 can include, but is not limited to, a transparent conductive oxide (TCO). In particular, the first electrode 210 can include indium tin oxide (ITO), indium zinc oxide (IZO), indium tin zinc oxide (ITZO), SnO, ZnO, indium cerium oxide (ICO), and aluminum-doped zinc oxide (AZO).

[0068] In one exemplary embodiment, when the organic light-emitting display device 100 is a bottom-emission type, the first electrode 210 may have a single-layer TCO structure. Alternatively, when the organic light-emitting display device 100 is a top-emission type, a reflective electrode or reflective layer may be disposed below the first electrode 210. For example, the reflective electrode or reflective layer may include, but is not limited to, silver (Ag) or an aluminum-palladium-copper (APC) alloy. In a top-emission type organic light-emitting display device 100, the first electrode 210 may have a three-layer structure of ITO / Ag / ITO or ITO / APC / ITO.

[0069] In addition, in order to cover the edge of the first electrode 210, a bank layer 164 is disposed on the passivation layer 160. The bank layer 164 exposes the center of the first electrode 210. The bank layer 164 may be omitted.

[0070] The light emitting layer 230 is disposed on the first electrode 210. In an exemplary embodiment, the light emitting layer 230 may have a single-layer structure of a light emitting material layer (EML). Alternatively, the light emitting layer 230 may have a multilayer structure of a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an EML, a hole blocking layer (HBL), an electron transport layer (ETL), and / or an electron injection layer (EIL), as shown in FIG. Figure 3 and 4 The light emitting layer 230 may have a single light emitting portion or may have multiple light emitting portions to form a series structure.

[0071] The light-emitting layer 230 can include at least one light-emitting material layer comprising an anthracene compound and a boron compound in which at least one hydrogen atom is tritiated in the blue pixel region, and at least one electron-blocking layer comprising an arylamine compound. Alternatively, the light-emitting layer 230 can further include at least one hole-blocking layer comprising at least one of an azine compound and a benzimidazole compound. The light-emitting layer 230 can significantly improve the luminous efficiency and lifetime of the OLED D and the organic light-emitting display device 100.

[0072] The second electrode 220 is disposed on the substrate 102 on which the light-emitting layer 230 is disposed. The second electrode 220 can be disposed over the entire display area and can include a conductive material having a relatively lower work function value than the first electrode 210, and can serve as a cathode. For example, the second electrode 220 can include, but is not limited to, highly reflective materials such as aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), alloys thereof, or combinations thereof, such as an aluminum-magnesium alloy (Al-Mg). When the organic light-emitting display device 100 is a top-emitting type, the second electrode 220 is very thin, making it light-transmissive (semi-transmissive).

[0073] In addition, in order to prevent external moisture from penetrating into the organic light emitting diode D, an encapsulation film 170 may be disposed on the second electrode 220. The encapsulation film 170 may have, but is not limited to, a stacked structure of a first inorganic insulating film 172, an organic insulating film 174, and a second inorganic insulating film 176. The encapsulation film 170 may be omitted.

[0074] The organic light-emitting display device 100 may further include a polarizing plate to reduce reflection of external light. For example, the polarizing plate may be a circular polarizing plate. When the organic light-emitting display device 100 is a bottom-emitting type, the polarizing plate may be located below the substrate 102. Alternatively, when the organic light-emitting display device 100 is a top-emitting type, the polarizing plate may be attached to the encapsulation film 170. In addition, in a top-emitting organic light-emitting display device 100, a cover window may be attached to the encapsulation film 170 or the polarizing plate. In this case, the substrate 102 and the cover window are flexible, thereby constructing a flexible display device.

[0075] As described above, the light emitting layer 230 in the organic light emitting diode D includes a specific compound, so that the organic light emitting diode D can improve its light emitting efficiency and light emitting life. Figure 3 is a cross-sectional view illustrating an organic light emitting diode having a single light emitting portion according to an exemplary embodiment of the present disclosure.

[0076] like Figure 3 As shown, an organic light emitting diode (OLED) D1 according to a first embodiment of the present disclosure includes a first electrode 210 and a second electrode 220 facing each other, and a light emitting layer 230 disposed between the first electrode 210 and the second electrode 220. In an exemplary embodiment, the light emitting layer 230 includes an EML 340 and an EBL 330. The EML 340 may be a first EML disposed between the first and second electrodes 210 and 220, and the EBL 330 may be a first EBL disposed between the first electrode 210 and the EML 340. Alternatively, the light emitting layer 230 may further include an HBL 350, which may be a first HBL disposed between the EML 340 and the second electrode 220.

[0077] In addition, the light emitting layer 230 may further include a HIL 310 disposed between the first electrode 210 and the EBL 330 and a HTL 320 disposed between the HIL 310 and the EBL 330. In addition, the light emitting layer 230 may further include an EIL 360 disposed between the HBL 350 and the second electrode 220. In an alternative embodiment, the light emitting layer 230 may further include an ETL disposed between the HBL 350 and the EIL 360. Organic light emitting display device 100 ( Figure 2 ) includes a red pixel area, a green pixel area and a blue pixel area, and the OLED D1 can be located in the blue pixel area.

[0078] One of the first electrode 210 and the second electrode 220 may be an anode, and the other of the first electrode 210 and the second electrode 220 may be a cathode. In addition, one of the first electrode 210 and the second electrode 220 may be a transmissive (semi-transmissive) electrode, and the other of the first electrode 210 and the second electrode 220 may be a reflective electrode. For example, the thickness of each of the first electrode 210 and the second electrode 220 may be, but is not limited to, about 30 nm to about 300 nm.

[0079] EML 340 includes a boron-based compound dopant 342 (which may be a first dopant) and an anthracene-based compound host 344 (which may be a first host), thereby causing EML 340 to emit blue (B) light. In this case, boron-based compound dopant 342 may be partially or partially deuterated, while at least one hydrogen atom in anthracene-based compound host 344 may be deuterated. In other words, host 344 in EML 340 may be partially or completely deuterated, while dopant 342 may be partially or partially deuterated. Boron-based compound dopant 342 may have the following structure of Formula 1A or Formula 1B.

[0080] [Formula 1A]

[0081]

[0082] Among them, R 11 to R 14 and R 21 to R 24 Each independently selected from hydrogen, C1-C 10 Alkyl, C6-C 30 Aryl, C6-C 30 Arylamino, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups, or R 11 to R 14 and R 21 to R 24 The two adjacent ones form a fused ring, where R11 to R 14 and R 21 to R 24 The aryl, arylamino, heteroaryl and alicyclic groups are each independently free of substituents or substituted with at least one C1-C 10 Alkyl; R 31 and R 41 Each independently selected from hydrogen, C1-C 10 Alkyl, C6-C 30 Aryl, C6-C 30 Arylamino, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups, wherein R 31 and R 41 The aryl, arylamino, heteroaryl and alicyclic groups are each independently free of substituents or substituted with at least one C1-C 10 Alkyl; R 51 Selected from hydrogen, C1-C 10 Alkyl, C3-C 15 Cycloalkyl, C6-C 30 Aryl, C6-C 30 Arylamino, C5-C 30 Heteroaryl, C3-C 30 Alicyclic and C5-C 30 A group consisting of heterocyclic groups, wherein R 51 The cycloalkyl, aryl, arylamino, heteroaryl, alicyclic and heterocyclic groups are each independently free of substituents or substituted with at least one C1-C 10 Alkyl; when R 31 、R 41 and R 51 Each is substituted with at least one C1-C 10 Alkyl C6-C 30 In the case of an aryl group, the substituted alkyl groups are linked to each other to form a condensed ring.

[0083] [Formula 1B]

[0084]

[0085] wherein X is NR1, CR2R3, O, S, Se or SiR4R5, and R1 to R5 are each independently selected from hydrogen, C1-C 10 Alkyl, C6-C 30 Aryl, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups; R 61 to R 64 Each independently selected from hydrogen, C1-C 10 Alkyl, C6-C30 Aryl, C6-C 30 Arylamino, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups, or R 61 to R 64 The two adjacent ones form a fused ring, where R 61 to R 64 The aryl, arylamino, heteroaryl and alicyclic groups are each independently free of substituents or substituted with at least one C1-C 10 Alkyl; R 71 to R 74 Each independently selected from hydrogen, C1-C 10 Alkyl and C3-C 30 A group consisting of alicyclic groups; R 81 Choose from C6-C 30 Aryl, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups, or R 81 and R 61 Form a fused ring, where R 81 The aryl, heteroaryl and alicyclic groups are each independently free of substituents or substituted with at least one C1-C 10 Alkyl; R 82 Choose from C6-C 30 Aryl, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups, wherein R 82 The aryl, heteroaryl and alicyclic groups are each independently free of substituents or substituted with at least one C1-C 10 Alkyl; R 91 Selected from hydrogen, C1-C 10 Alkyl, C3-C 15 Cycloalkyl, C6-C 30 Aryl, C6-C 30 Arylamino, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups, wherein R 91 The cycloalkyl, aryl, arylamino, heteroaryl and alicyclic groups are each independently unsubstituted or substituted with at least one C1-C 10 Alkyl; when R 81 、R 82 and R 91 Each is substituted with at least one C1-C 10 Alkyl C6-C 30 In the case of an aryl group, the substituted alkyl groups are linked to each other to form a condensed ring.

[0086] As an example, R in Formula 1A11 to R 14 、R 21 to R 24 、R 31 and R 41 Each can be independently selected from hydrogen, C1-C 10 Alkyl, C6-C 30 Aryl and C5-C 30 The group consisting of heteroaryl groups, wherein R 11 to R 14 、R 21 to R 24 、R 31 and R 41 The aryl and heteroaryl groups may each independently be unsubstituted or substituted with C1-C 10 alkyl, and R in Formula 1A 51 You can choose from C1-C 10 Alkyl, C6-C 30 Arylamino, C5-C 30 Heteroaryl and C3-C 30 A group consisting of a heterocyclic group, and wherein R 51 The heteroaryl, arylamino and heterocyclic groups may each independently be unsubstituted or substituted with C1-C 10 alkyl.

[0087] For example, in Formula 1A, R 11 to R 14 One of and / or R 21 to R 24 One of them can be C1-C 10 Alkyl, and R 11 to R 14 The remaining groups and / or R 21 to R 24 The remaining groups in may be hydrogen, and R 31 and R 41 Each may be independently substituted with C1-C 10 Phenyl or substituted C1-C 10 Alkyl dibenzofuranyl. R in Formula 1A 51 Can be C1-C 10 In this case, the alkyl group may be, but is not limited to, a tert-butyl group. In addition, the condensed ring formed by the adjacent groups may be, but is not limited to, a C3-C 10 Alicyclic.

[0088] Alternatively, X in Formula 1B may be O or S, and R in Formula 1B may be 61 to R 64Each can be independently selected from hydrogen, C1-C 10 Alkyl and C6-C 30 A group consisting of an arylamino group, or R 61 to R 64 Two adjacent rings can form a fused ring, R 71 to R 74 Each can be independently selected from hydrogen and C1-C 10 The group consisting of alkyl groups, R 81 You can choose from C6-C 30 Aryl and C5-C 30 A group consisting of heteroaryl groups, or R 81 and R 61 Can form a fused ring, where R 81 The aryl and heteroaryl groups may each independently be unsubstituted or substituted with C1-C 10 Alkyl, R 82 You can choose from C6-C 30 Aryl and C5-C 30 The group consisting of heteroaryl groups, wherein R 82 The aryl and heteroaryl groups may each independently be unsubstituted or substituted with C1-C 10 alkyl, and wherein R 91 Can be C1-C 10 alkyl.

[0089] For example, X in Formula 1B may be O. 61 to R 64 Each can be independently selected from protium, deuterium, C1-C 10 A group consisting of an alkyl group and a diphenylamino group, or R 61 to R 64 Two adjacent groups may form a fused ring, and the diphenylamino group or the fused group may be deuterated. 71 to R 74 Each can be independently selected from protium, deuterium and C1-C 10 A group consisting of an alkyl group. 81 and R 82 Each may be independently selected from the group consisting of: each may be independently unsubstituted or substituted with deuterium and / or C1-C 10 The alkyl group consists of phenyl and dibenzofuranyl. 91 Can be C1-C 10 Alkyl groups, such as tert-butyl, but not limited thereto.

[0090] Alternatively, in Formula 1B, R 73 Can be C1-C 10 Alkyl, and R 71 、R 72 and R 74Each can be independently protium or deuterium. For example, in the boron compound having the structure of Formula 1B, at least one protium connected to the aromatic ring and the heteroaromatic ring other than the aromatic ring connected to the boron atom and the two nitrogen atoms and the aromatic ring fused by those heteroaromatic rings can be replaced by deuterium. That is, R in Formula 1B 91 Deuterium substitution is not required.

[0091] For example, the boron compound dopant 342 may be selected from, but not limited to, the compounds of Formula 2 below:

[0092] [Formula 2]

[0093]

[0094]

[0095] In another exemplary aspect, the host 344 of the anthracene-based compound may have a structure of Formula 3 below:

[0096] [Formula 3]

[0097]

[0098] wherein Ar1 and Ar2 are each independently C6-C 30 Aryl or C5-C 30 Heteroaryl; L is a single bond, C6-C 20 Arylene or C5-C 20 a is an integer from 0 to 8; b, c and d are each independently an integer from 0 to 30, wherein at least one of a, b, c and d is a positive integer.

[0099] As an example, in Formula 3, Ar1 and Ar2 can each independently be a phenyl group, a naphthyl group, a dibenzofuranyl group, or a fused dibenzofuranyl group, and L can be a single bond, a phenylene group, or a dibenzofuranyl group. For example, in Formula 3, Ar1 can be a naphthyl group, a dibenzofuranyl group, or a fused dibenzofuranyl group, and Ar2 can be a phenyl group or a naphthyl group. Alternatively, both Ar1 and Ar2 can be naphthyl groups, and L can be a single bond, a phenylene group, or a dibenzofuranyl group.

[0100] In particular, the 1-naphthyl moiety is directly linked to the anthracenyl moiety, the 2-naphthyl moiety is directly linked to the anthracenyl moiety or through a phenylene linker (bridging group), and at least one protium in the molecule (e.g., all protiums) may be deuterated.

[0101] For example, the host 344 of the anthracene compound may be selected from, but not limited to, the compound of Formula 4 below:

[0102] [Formula 4]

[0103]

[0104] In one exemplary embodiment, the content of the host 344 in the EML 340 may be approximately 70 wt% to approximately 99.9 wt%, and the content of the dopant 342 may be approximately 0.1 wt% to approximately 30 wt%. For example, the content of the dopant 342 in the EML 340 may be approximately 0.1 wt% to approximately 10 wt%, for example, approximately 1 wt% to approximately 5 wt%, so that the EML 340 can achieve sufficient luminous efficiency and luminous lifetime. The thickness of the EML 340 may be, but is not limited to, approximately 10 nm to approximately 200 nm, for example, approximately 20 nm to approximately 100 nm or approximately 20 nm to approximately 50 nm.

[0105] EML 340 includes a boron-based dopant 342 and a host 344 of an anthracene-based compound substituted with at least one deuterium, thereby improving the luminous efficiency and lifetime of OLED D1 and organic light-emitting display device 100. When boron-based dopant 342 has an asymmetric chemical structure as shown in Formula 1B, OLED D1 and organic light-emitting display device 100 can significantly improve their luminous efficiency and lifetime.

[0106] In addition, when the EML 340 includes the dopant 342 in which part or all of the protium bonded to aromatic rings and heteroaromatic rings other than the aromatic ring bonded to the boron atom and the two nitrogen atoms may be substituted with deuterium, the OLED D1 and the organic light-emitting display device 100 may further improve their luminous efficiency and luminous lifetime.

[0107] In addition, when the EML 340 includes a host 344 of an anthracene-based compound in which two naphthyl moieties are connected to an anthracene moiety directly or through a linker and at least one (e.g., all) protium is deuterated, the luminous efficiency and luminous lifetime of the OLED D1 and the organic light-emitting display device 100 can be further improved.

[0108] The HIL 310 is disposed between the first electrode 210 and the HTL 320 and improves interface characteristics between the inorganic first electrode 210 and the organic HTL 320. In one exemplary embodiment, the HIL 310 may include a hole injection material selected from, but not limited to, the group consisting of: 4,4'4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4"-tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4',4"-tris(N-(naphthalen-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-tris(N-(naphthalen-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazolyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-di(1-naphthyl)-1,1'-biphenyl- 4,4″-diamine (NPB; NPD), 1,4,5,8,9,11-hexaazatriphenylene hexacarbonitrile (dipyrazino[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile; HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene)polystyrenesulfonic acid (PEDOT / PSS), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, and combinations thereof.

[0109] Alternatively, HIL 340 may include a hole injection host and a hole injection dopant. As an example, the hole injection host may include a spirofluorene compound having a structure of Formula 11 below, and the hole injection dopant may include a radialene compound having a structure of Formula 12 below, but are not limited thereto.

[0110] [Equation 11]

[0111]

[0112] [Equation 12]

[0113]

[0114] When HIL 310 includes a hole injection host and a hole injection dopant, the content of the hole injection dopant in HIL 310 may be, but is not limited to, about 1 wt % to about 50 wt %, for example, about 1 wt % to about 30 wt %. HIL 310 may be omitted if it meets the characteristics of OLED D1.

[0115] The HTL 320 is disposed between the HIL 310 and the EBL 330. In one exemplary embodiment, the HTL 320 may include a hole injection material selected from, but not limited to, N,N'-diphenyl-N,N'-di(3-methylphenyl-1,1'-biphenyl-4,4'-diamine (TPD), NPB (NPD), N,N'-di[4-[di(3-methylphenyl)amino]phenyl]-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD), 4,4'-di(N-carbazolyl)-1,1'-biphenyl (CBP), poly[N,N'-di(4-butylphenyl)-N,N'-di(phenyl)-benzidine] (poly-TPD), poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))] (TFB), 1,1-di(4-(N,N'-di(p-toluene))] 9H-fluoren-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, 1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine and / or a spirofluorene compound having a structure of Formula 11.

[0116] In an exemplary embodiment, the thickness of each of the HIL 310 and the HTL 320 may independently be, but is not limited to, about 5 nm to about 200 nm, for example, about 5 nm to about 100 nm.

[0117] The EBL 330 prevents electrons from being transferred from the EML 340 to the first electrode 210. The EBL 330 may include an electron blocking material 332 of a spiroarylamine-based compound having a structure of Formula 5 below.

[0118] [Formula 5]

[0119]

[0120] Among them, L3 is C6-C 30 Arylene; o is 0 or 1; R 121 and R 122 Each independently is C6-C 30 Aryl or C5-C 30 Heteroaryl, wherein the C6-C30 Aryl or the C5-C 30 Heteroaryl groups are each optionally substituted with C1-C 10 Alkyl and C6-C 30 At least one of the aryl groups.

[0121] As an example, L3 can be phenylene, and R 121 to R 122 Each may independently have no substituent or be substituted with C1-C 10 Alkyl and C6-C 30 At least one of an aryl group (eg, a phenyl group), and may be selected from the group consisting of a phenyl group, a biphenyl group, a fluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a carbazolylphenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.

[0122] For example, the electron blocking material 332 may be selected from any spiroarylamine compound having the structure of Formula 6 below:

[0123] [Formula 6]

[0124]

[0125]

[0126] Alternatively, the OLED D1 may further include an HBL 350 that prevents holes from being transferred from the EML 340 to the second electrode 220. As an example, the HBL 350 may include a hole blocking material 352 of an azine-based compound having a structure of Formula 7 below and / or a benzimidazole-based compound having a structure of Formula 9 below.

[0127] [Formula 7]

[0128]

[0129] wherein Y1 to Y5 are each independently CR 131 or N, one to three of Y1 to Y5 are N, and R 131 It is C6-C 30 Aryl; L is C6-C 30 Arylene; R 132 It is C6-C 30 Aryl or C5-C 30 Heteroaryl, wherein C6-C 30 Aryl is optionally substituted with another C6-C 30 Aryl or C5-C 30 Heteroaryl, or with C 10 -C 30 Fused aryl ring or C 10 -C 30The fused heteroaryl ring forms a spirocyclic structure, wherein the other C6-C 30 The aryl group may be further substituted with other C6-C 30 Aryl or C5-C 30 Heteroaryl, or with C 10 -C 30 The fused aromatic rings form a spiro ring structure; R 133 is hydrogen, or two adjacent R 133 forming a fused aromatic ring; r is 0 or 1; s is 1 or 2; and t is an integer from 0 to 4;

[0130] [Formula 9]

[0131]

[0132] Where Ar is C 10 -C 30 Arylene; R 141 It is C6-C 30 Aryl or C5-C 30 Heteroaryl, C6-C 30 Aryl and C5-C 30 The heteroaryl groups are each optionally substituted with C1-C 10 alkyl; and R 142 and R 143 are independently hydrogen, C1-C 10 Alkyl or C6-C 30 Aryl.

[0133] In an exemplary embodiment, R 132 The aryl group may have no substituent or may be further substituted with C6-C 30 Aryl or C5-C 30 Heteroaryl, or with other fused aryl rings or fused heteroaryl rings to form a spiro ring structure. For example, R 132 The aryl or heteroaryl group may be C 10 -C 30 Fused aromatic or C 10 -C 30 Fused heteroaryl. R in Formula 7 133 In one exemplary embodiment, the azine compound used as the hole blocking material 352 may be selected from any azine compound having a structure of the following formula 8:

[0134] [Formula 8]

[0135]

[0136]

[0137] As an example, "Ar" in Formula 9 can be naphthyl or anthracenyl, and R in Formula 9 can be 141 It can be phenyl or benzimidazole, R in formula 9 142 It can be methyl, ethyl or phenyl. R in formula 9 143 In one exemplary embodiment, the benzimidazole compound used as the hole blocking material 352 may be selected from any benzimidazole compound having the structure of the following formula 10:

[0138] [Equation 10]

[0139]

[0140] In an exemplary embodiment, the thickness of the EBL 330 and the HBL 350 may each independently be, but is not limited to, about 5 nm to about 200 nm, for example, about 5 nm to about 100 nm.

[0141] The compounds having structures of Formulae 7 to 10 have good electron transport properties and excellent hole blocking properties. Therefore, the HBL 350 including the compounds having structures of Formulae 7 to 10 can function as a hole blocking layer and an electron transport layer.

[0142] In another embodiment, the OLED D1 may further include an ETL disposed between the HBL 350 and the EIL 360. In an exemplary embodiment, the ETL may include, but is not limited to, oxadiazole compounds, triazole compounds, phenanthroline compounds, benzoxazole compounds, benzothiazole compounds, benzimidazole compounds, triazine compounds, and the like.

[0143] In particular, the ETL may include an electron transport material selected from, but not limited to, the group consisting of tris-(8-hydroxyquinoline)aluminum (Alq3), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, hydroxyquinoline lithium (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(naphthalene-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-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole 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), biphenyl-4-triazine Phenylsilyl-phenylphosphine oxide (TSPO1), 2-[4-(9,10-di-2-naphthyl-2-anthryl)phenyl]-1-phenyl-1H-benzimidazole (ZADN), 1,3-bis(9-phenyl-1,10-phenanthroline-2-yl)benzene, 1,4-bis(2-phenyl-1,10-phenanthroline-4-yl)benzene (p-bPPhenB) and / or 1,3-bis(2-phenyl-1,10-phenanthroline-4-yl)benzene (m-bPPhenB).

[0144] The EIL 360 is disposed between the HBL 350 and the second electrode 220 and can improve the physical properties of the second electrode 320, thereby increasing the lifespan of the OLED D1. In one exemplary embodiment, the EIL 360 may include, but is not limited to, alkali metal halides or alkaline earth metal halides (e.g., LiF, CsF, NaF, BaF2, etc.) and / or organometallic compounds (e.g., Liq, lithium benzoate, sodium stearate, etc.).

[0145] In another embodiment, the EIL 360 may be an organic layer doped with an alkali metal (e.g., Li, Na, K, and / or Cs) and / or an alkaline earth metal (e.g., Mg, Sr, Ba, and / or Ra). The organic host used in the EIL 360 may be an electron transport material, and the content of the alkali metal and / or alkaline earth metal in the EIL 360 may be, but is not limited to, about 1 wt % to about 30 wt %. For example, the EIL 360 may include an electron transport material having a structure of the following Formula 13:

[0146] [Equation 13]

[0147]

[0148] As an example, the thickness of the ETL and the EIL 360 may each independently be about 10 nm to about 200 nm, for example, about 10 nm to 100 nm.

[0149] The OLED D1 can maximize its luminous efficiency and luminous lifetime by applying a dopant 342 of a boron-based compound having structures of Formulas 1A to 2 and a host 344 of an anthracene-based compound having structures of Formulas 3 to 4 to the EML 340, applying arylamine-based compounds having structures of Formulas 5 and 6 to the EBL 330, and optionally applying azine-based compounds having structures of Formulas 7 to 8 and / or benzimidazole-based compounds having structures of Formulas 9 to 10 to the HBL 350.

[0150] In the first exemplary embodiment, the OLED D1 may have a single light emitting portion. The OLED of the present disclosure may have a tandem structure including a plurality of light emitting portions. Figure 4 is a schematic cross-sectional view illustrating an organic light emitting diode having two light emitting parts according to another exemplary embodiment of the present disclosure.

[0151] like Figure 4 As shown, the OLED D2 according to the second embodiment of the present disclosure includes a first electrode 210 and a second electrode 220 facing each other, and a light-emitting layer 230A disposed between the first electrode 210 and the second electrode 220. The light-emitting layer 230A includes a first light-emitting portion 400 disposed between the first electrode 210 and the second electrode 220, a second light-emitting portion 500 disposed between the first light-emitting portion 400 and the second electrode 220, and a charge generation layer (CGL) 470 disposed between the first light-emitting portion 400 and the second light-emitting portion 500. The organic light-emitting display device 100 ( Figure 2 ) includes a red pixel area, a green pixel area and a blue pixel area, and the OLED D2 can be located in the blue pixel area.

[0152] One of the first electrode 210 and the second electrode 220 may be an anode, and the other of the first electrode 210 and the second electrode 220 may be a cathode. In addition, one of the first electrode 210 and the second electrode 220 may be a transmissive (semi-transmissive) electrode, and the other of the first electrode 210 and the second electrode 220 may be a reflective electrode.

[0153] The first light-emitting portion 400 includes a first light-emitting material layer (EML1) 440 disposed between the first electrode 210 and the CGL 470. The first light-emitting portion 400 may include a first electron blocking layer (EBL1) 430 disposed between the first electrode 210 and the EML1 440, and optionally a first hole blocking layer (HBL1) 450 disposed between the EML1 440 and the CGL 470. In addition, the first light-emitting portion 400 may further include a HIL 410 disposed between the first electrode 210 and the EBL1 430, and a first hole transport layer (HTL1) 420 disposed between the HIL 410 and the EBL1 430.

[0154] The second light-emitting portion 500 includes a second light-emitting material layer (EML2) 540 disposed between the CGL 470 and the second electrode 220. The second light-emitting portion 500 may include a second electron blocking layer (EBL2) 530 disposed between the CGL 470 and the EML2 540, and optionally a second hole blocking layer (HBL2) 550 disposed between the EML2 540 and the second electrode 220. In addition, the second light-emitting portion 500 may further include a second hole transport layer (HTL2) 520 disposed between the CGL 470 and the EBL2 530, and an EIL 560 disposed between the HBL2 550 and the second electrode 220. The HIL 410, HTL1 420, HTL2 520, and EIL 560 may each independently include the same materials as described above. The HTL1 420 may include the same material as the HTL2 520 or a different material.

[0155] EML1 440 includes a first dopant 442 of a boron-based compound and a first host 444 of an anthracene-based compound, thereby emitting blue (B) light. EML2 540 includes a second dopant 542 of a boron-based compound and a second host 544 of anthracene-based compound, thereby emitting blue (B) light.

[0156] The first dopant 442 and the second dopant 542 of the boron-based compound may each be undeuterated or partially deuterated and may independently have the structures of Formulas 1A to 2. The first host 444 and the second host 544 of the anthracene-based compound may each be at least partially deuterated and may independently have the structures of Formulas 3 to 4. The first dopant 442 may be the same as or different from the second dopant 542, and the first host 444 may be the same as or different from the second host 544.

[0157] In one exemplary embodiment, the first host 444 and the second host 544 in each of EML1 440 and EML2 540 may each independently contain about 70 wt% to about 99.9 wt%, and the first dopant 442 and the second dopant 542 may each independently contain about 0.1 wt% to about 30 wt%. For example, the first dopant 442 and the second dopant 542 in each of EML1 440 and EML2 540 may each contain about 0.1 wt% to about 10 wt%, for example, about 1 wt% to about 5 wt%, so that both EML1 440 and EML2 540 can achieve sufficient luminous efficiency and luminous lifetime.

[0158] Each of EBL1 430 and EBL2 530 blocks electrons from being transported from EML1 440 or EML2 540 to first electrode 210 or CGL 470, respectively. Each of EBL1 430 and EBL2 530 may include a first electron blocking material 432 and a second electron blocking material 532, respectively. The first electron blocking material 432 and the second electron blocking material 532 may each independently include an amine compound having a structure of Formulae 5 to 6. The first electron blocking material 432 may be the same as or different from the second electron blocking material 532.

[0159] HBL1 450 and HBL2 550 each block holes from being transported from EML1 440 or EML2 540 to CGL 470 or second electrode 220. HBL1 450 and HBL2 550 each may include a first hole blocking material 452 and a second hole blocking material 552, respectively. The first hole blocking material 452 and the second hole blocking material 552 each may independently include an azine compound having a structure of Formulae 7 to 8 and / or a benzimidazole compound having a structure of Formulae 9 to 10. The first hole blocking material 452 may be the same as or different from the second hole blocking material 552.

[0160] As described above, the compounds having the structures of Formulae 7 to 10 have excellent electron transport properties and excellent hole blocking properties. Therefore, HBL1 450 and HBL2 550 can each function as a hole blocking layer and an electron transport layer.

[0161] In alternative embodiments, the first light emitting portion 400 may further include a first electron transport layer (ETL1) disposed between the HBL1 450 and the CGL 470 , and / or the second light emitting portion 500 may further include a second electron transport layer (ETL2) disposed between the HBL2 550 and the EIL 560 .

[0162] The CGL 470 is disposed between the first light-emitting portion 400 and the second light-emitting portion 500, so that the first light-emitting portion 400 and the second light-emitting portion 500 are connected through the CGL 470. The CGL 470 may be a PN junction CGL having an N-type CGL (N-CGL) 480 and a P-type CGL (P-CGL) 490. The N-CGL 480 is disposed between the HBL1 450 and the HTL2 520, and the P-CGL 490 is disposed between the N-CGL 480 and the HTL2 520. The N-CGL 480 injects electrons into the first light-emitting portion 400, and the P-CGL 490 injects holes into the second light-emitting portion 500.

[0163] As an example, the N-CGL 480 may be an organic layer doped with an alkali metal (e.g., Li, Na, K, and / or Cs) and / or an alkaline earth metal (e.g., Mg, Sr, Ba, and / or Ra). For example, the organic host used in the N-CGL 480 may include, but is not limited to, organic compounds such as Bphen or MTDATA. The N-CGL 480 may be doped with an alkali metal and / or alkaline earth metal in an amount of approximately 0.01 wt % to approximately 30 wt %.

[0164] The P-CGL 490 may include, but is not limited to, a material selected from tungsten oxide (WO x ), molybdenum oxide (MoO x ), an inorganic material selected from the group consisting of beryllium oxide (Be2O3), vanadium oxide (V2O5) and a combination thereof, and / or an organic material selected from the group consisting of NPD, HAT-CN, F4TCNQ, TPD, N,N,N',N'-tetranaphthyl-benzidine (TNB), TCTA, N,N'-dioctyl-3,4,9,10-perylene dicarboximide (PTCDI-C8) and a combination thereof.

[0165] Alternatively, the P-CGL 490 may include a P-type body having a structure of Formula 11 and a P-type dopant having a structure of Formula 12. When the P-CGL 490 includes the P-type body and the P-type dopant, the content of the P-type dopant in the P-CGL 490 may be, but is not limited to, about 1 wt % to about 50 wt %, for example, about 1 wt % to about 30 wt %.

[0166] Each of EML1 440 and EML2 540 includes a first dopant 442 and a second dopant 542 of a boron-based compound, and a first host 444 and a second host 544 of an anthracene-based compound in which at least one carbon atom is deuterated. The first dopant 442 and the second dopant 542 of the boron-based compound can each independently have an asymmetric chemical structure as shown in Formula 1B and can be undeuterated or partially deuterated. In addition, the first host 444 and the second host 544 of the anthracene-based compound can each have a structure in which two naphthyl moieties are directly or via a linker connected to an anthracene moiety, and at least one protium (e.g., all protium) is deuterated. As a result, OLED D2 and organic light-emitting display device 100 can improve their luminous efficiency and luminous life.

[0167] In addition, the OLED D2 and the organic light-emitting display device 100 can maximize their luminous efficiency and luminous lifetime by applying the arylamine compounds having the structures of Formula 5 and Formula 6 as the first and second electron blocking materials 432 and 532 to the EBL1 430 and EBL2 530, respectively, and optionally applying the azine compounds having the structures of Formulas 7 to 8 and / or the benzimidazole compounds having the structures of Formulas 9 to 10 as the first hole blocking material 452 and the second hole blocking material 552 to the HBL1 450 and HBL2 550, respectively. In addition, the organic light-emitting display device 100 (see Figure 2 ) An image with high color purity can be achieved by stacking a double stack structure of two light-emitting portions 400 and 500, each of which emits blue light.

[0168] In the second embodiment, the OLED D2 has a series structure of two light emitting parts. Alternatively, the OLED may include three or more light emitting parts, for example, a second CGL and a third light emitting part arranged on the second light emitting part 500 in addition to the EIL 560 (see FIG. Figure 7 ).

[0169] In the above embodiment, the organic light emitting display device 100 and the OLEDs D1 and D2 realize blue light (B) emission. Alternatively, the organic light emitting display device and the OLEDs can realize a full-color display device including white light (W) emission. Figure 5 is a schematic cross-sectional view illustrating an organic light emitting display device according to another exemplary embodiment of the present disclosure.

[0170] like Figure 5As shown, the organic light-emitting display device 600 includes: a first substrate 602 that defines a red pixel area RP, a green pixel area GP, and a blue pixel area BP, a second substrate 604 facing the first substrate 602, a thin film transistor Tr on the first substrate 602, an organic light-emitting diode D arranged between the first substrate 602 and the second substrate 604 and emitting white (W) light, and a color filter layer 680 arranged between the organic light-emitting diode D and the second substrate 604.

[0171] Each of the first substrate 602 and the second substrate 604 may include, but is not limited to, glass, flexible materials, and / or polymer plastics. For example, each of the first substrate 602 and the second substrate 604 may be made of PI, PES, PEN, PET, PC, or a combination thereof. The first substrate 602, on which the thin film transistors Tr and the organic light emitting diodes D are arranged, forms an array substrate.

[0172] A buffer layer 606 may be provided on the first substrate 602, and thin film transistors Tr corresponding to the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP are each provided on the buffer layer 606. The buffer layer 606 may be omitted.

[0173] A semiconductor layer 610 is disposed on the buffer layer 606. The semiconductor layer 610 may be made of an oxide semiconductor material or polysilicon.

[0174] A gate insulating layer 620 is provided on the semiconductor layer 610 and includes an insulating material, for example, an inorganic insulating material such as silicon oxide (SiO x ) or silicon nitride (SiN x ).

[0175] A gate electrode 630 made of a conductive material such as metal is disposed on the gate insulating layer 620 so as to correspond to the center of the semiconductor layer 610. An interlayer insulating layer 640 is provided on the gate electrode 630 and includes an insulating material, for example, an inorganic insulating material such as silicon oxide (SiO x ) or silicon nitride (SiN x ), or organic insulating materials such as benzocyclobutene or photoacrylic.

[0176] The interlayer insulating layer 640 has a first semiconductor layer contact hole 642 and a second semiconductor layer contact hole 644, exposing both sides of the semiconductor layer 610. The first semiconductor layer contact hole 642 and the second semiconductor layer contact hole 644 are arranged on opposite sides of the gate 630 and are spaced apart from the gate 630.

[0177] A source electrode 652 and a drain electrode 654 made of a conductive material such as metal are provided on the interlayer insulating layer 640. The source electrode 652 and the drain electrode 654 are spaced apart from each other relative to the gate electrode 630 and contact both sides of the semiconductor layer 610 through the first semiconductor layer contact hole 642 and the second semiconductor layer contact hole 644, respectively.

[0178] The semiconductor layer 610 , the gate electrode 630 , the source electrode 652 , and the drain electrode 654 constitute a thin film transistor Tr, which functions as a driving element.

[0179] Although Figure 5 Although not shown, gate lines and data lines that intersect to define the pixel area, as well as switching elements connected to the gate lines and data lines, may be further formed in the pixel area. The switching element is connected to a thin film transistor Tr serving as a driving element. In addition, the power line is spaced apart in parallel with the gate line or the data line, and the thin film transistor Tr may further include a storage capacitor configured to constantly maintain a gate voltage during a frame.

[0180] A passivation layer 660 is disposed on the source electrode 652 and the drain electrode 654, and the thin film transistor Tr covers the entire first substrate 602. The passivation layer 660 has a drain contact hole 662, exposing the drain electrode 654 of the thin film transistor Tr.

[0181] An organic light emitting diode (OLED) D is located on the passivation layer 660. The OLED D includes a first electrode 710 connected to the drain electrode 654 of the thin film transistor Tr, a second electrode 720 opposite to the first electrode 710, and a light emitting layer 730 disposed between the first and second electrodes 710 and 720.

[0182] The first electrode 710 formed for each pixel region may be an anode and may include a conductive material having a relatively high work function value, such as TCO. As an example, the first electrode 710 may include ITO, IZO, TZO, SnO, ZnO, ICO, AZO, etc.

[0183] When the organic light-emitting display device 600 is a bottom-emission type, the first electrode 710 may have a single-layer TCO structure. Alternatively, when the organic light-emitting display device 600 is a top-emission type, a reflective electrode or reflective layer may be disposed below the first electrode 710. For example, the reflective electrode or reflective layer may include, but is not limited to, Ag or an APC alloy. In a top-emission type organic light-emitting display device 600, the first electrode 710 may have a three-layer structure of ITO / Ag / ITO or ITO / APC / ITO.

[0184] To cover the edge of the first electrode 710, a bank layer 664 is disposed on the passivation layer 660. The bank layer 664 exposes the center of the first electrode 710 corresponding to each of the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP. The bank layer 664 may be omitted.

[0185] The light emitting layer 730 including the light emitting portion is disposed on the first electrode 710. Since the OLED D emits white light in each of the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP, the light emitting layer 730 may be formed of a common layer without being divided into the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP.

[0186] like Figure 6 and Figure 7 As shown, the light emitting layer 730 may include a plurality of light emitting portions 800, 900, 1000, 1100, and 1200 and at least one charge generation layer 870, 1070, and 1170. Each of the light emitting portions 800, 900, 1000, 1100, and 1200 may include an EML and may further include at least one of a HIL, a HTL, an EBL, an HBL, an ETL, and / or an EIL.

[0187] The second electrode 720 is disposed on the first substrate 602 on which the light-emitting layer 730 is disposed. The second electrode 720 may be disposed over the entire display area and may include a conductive material having a relatively lower work function value than the first electrode 710, and may be a cathode. For example, the second electrode 720 may include, but is not limited to, Al, Mg, Ca, Ag, alloys thereof, and combinations thereof, such as Al-Mg.

[0188] In the organic light emitting display device 600 according to the second embodiment of the present disclosure, since light emitted from the light emitting layer 730 is incident on the color filter layer 680 through the second electrode 720 , the second electrode 720 has a relatively thin thickness so that the light can be transmitted.

[0189] The color filter layer 680 is disposed above the OLED D and includes a red color filter 682, a green color filter 684, and a blue color filter 686, which are disposed corresponding to the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP, respectively. Figure 5 Although not shown in FIG, the color filter layer 680 can be attached to the OLED through an adhesive layer. Alternatively, the color filter layer 680 can be directly arranged on the OLED D.

[0190] In addition, in order to prevent external moisture from penetrating into the organic light emitting diode D, an encapsulation film may be provided on the second electrode 720. The encapsulation film may have, but is not limited to, a laminated structure of a first inorganic insulating film, an organic insulating film, and a second inorganic insulating film (see FIG. Figure 2170 in FIG). Furthermore, the organic light-emitting display device 600 may further include a polarizing plate to reduce reflection of external light. For example, the polarizing plate may be a circular polarizing plate. When the organic light-emitting display device 600 is a bottom-emitting type, the polarizing plate may be located below the first substrate 602. Alternatively, when the organic light-emitting display device 600 is a top-emitting type, the polarizing plate may be located above the second substrate 604.

[0191] exist Figure 5 , light emitted from the OLED D is transmitted through the second electrode 720, and the color filter layer 680 is arranged above the OLED D. Alternatively, light emitted from the OLED D is transmitted through the first electrode 710, and the color filter layer 680 may be arranged between the OLED D and the first substrate 602. In addition, a color conversion layer may be formed between the OLED D and the color filter layer 680. The color conversion layer may include a red conversion layer, a green conversion layer, and a blue conversion layer, wherein each color conversion layer is arranged corresponding to each pixel region (RP, GP, and BP), thereby converting white (W) light into each of red, green, and blue light, respectively.

[0192] As described above, white (W) light emitted from the OLED D is transmitted through the red filter 682, the green filter 684, and the blue filter 686, each of which is provided corresponding to the red pixel area RP, the green pixel area GP, and the blue pixel area BP, respectively, thereby displaying red, green, and blue light in the red pixel area RP, the green pixel area GP, and the blue pixel area BP.

[0193] Figure 6 : is a schematic cross-sectional view showing an organic light emitting diode having two light emitting parts. Figure 6 As shown, an organic light emitting diode (OLED) D3 according to an exemplary embodiment includes a first electrode 710 and a second electrode 720, and a light emitting layer 730 disposed between the first electrode 710 and the second electrode 720. The light emitting layer 730 includes a first light emitting portion 800 disposed between the first electrode 710 and the second electrode 720, a second light emitting portion 900 disposed between the first light emitting portion 800 and the second electrode 720, and a charge generation layer (CGL) 870 disposed between the first light emitting portion 800 and the second light emitting portion 900.

[0194] One of the first electrode 710 and the second electrode 720 may be an anode, and the other of the first electrode 710 and the second electrode 720 may be a cathode. In addition, one of the first electrode 710 and the second electrode 720 may be a transmissive (semi-transmissive) electrode, and the other of the first electrode 710 and the second electrode 720 may be a reflective electrode.

[0195] In addition, one of the first light-emitting portion 800 and the second light-emitting portion 900 emits blue (B) light, and the other of the first light-emitting portion 800 and the second light-emitting portion 900 emits red-green (RG) or yellow-green (YG) light. Below, the OLED D3 in which the first light-emitting portion 800 emits blue (B) light and the second light-emitting portion 900 emits red-green (RG) and / or yellow-green (YG) light will be described in detail.

[0196] The first light-emitting portion 800 includes an EML1 840 disposed between the first electrode 710 and the CGL 870. The first light-emitting portion 800 may include an EBL1 830 disposed between the first electrode 710 and the EML1 840, and optionally, an HBL1 850 disposed between the EML1 840 and the CGL 870. In addition, the first light-emitting portion 800 may further include a HIL 810 disposed between the first electrode and the EBL1 830, and an HTL1 820 disposed between the HIL 810 and the EBL1 830. Alternatively, the first light-emitting portion 800 may further include an ETL1 disposed between the HBL1 850 and the CGL 870.

[0197] The second light-emitting portion 900 includes an EML2 940 disposed between the CGL 870 and the second electrode 720. The second light-emitting portion 900 may include an HTL 920 disposed between the CGL 870 and the EML2 940, an ETL2 950 disposed between the second electrode 720 and the EML2 940, and an EIL 960 disposed between the second electrode 720 and the ETL2 950. Alternatively, the second light-emitting portion 900 may further include an EBL2 disposed between the HTL2 920 and the EML2 940, and / or an HBL2 disposed between the EML2 940 and the ETL2 950.

[0198] The CGL 870 is disposed between the first light emitting portion 800 and the second light emitting portion 900. The CGL 870 may be a PN junction CGL having an N-CGL 870 and a P-CGL 890. The N-CGL 880 is disposed between the HBL1 850 and the HTL2 920, and the P-CGL 890 is disposed between the N-CGL 880 and the HTL2 920.

[0199] Each of the HIL 810 , HTL1 820 , HTL2 920 , EIL 560 , and CGL 870 may independently include the same materials as described above. The HTL1 820 may include the same material as the HTL2 920 or a different material.

[0200] EML1 840 includes a first dopant 842 of a boron-based compound and a first host 844 of an anthracene-based compound, thereby emitting blue (B) light. The first dopant 842 of the boron-based compound may be undeuterated or partially deuterated and may have a structure of Formulas 1A to 2. The first host 844 of the anthracene-based compound may be at least partially deuterated and may have a structure of Formulas 3 to 4.

[0201] In one exemplary embodiment, the first host 844 may be present in an amount of about 70 wt% to about 99.9 wt%, and the first dopant 842 may be present in an amount of about 0.1 wt% to about 30 wt% in the EML1 840. For example, the first dopant 844 may be present in an amount of about 0.1 wt% to about 10 wt%, for example, about 1 wt% to about 5 wt%, in the EML1 840 to achieve sufficient luminous efficiency and luminous lifetime.

[0202] The EBL1 830 prevents electrons from being transferred from the EML1 840 to the first electrode 710 and may include an electron blocking material 832. The electron blocking material 832 may include an amine compound having a structure of Formulae 5 to 6.

[0203] HBL1 850 prevents holes from being transported from EML1 840 to CGL 870 and may include a hole-blocking material 852. Hole-blocking material 852 may include azine compounds having structures of Formulae 7 to 8 and / or benzimidazole compounds having structures of Formulae 9 to 10. As described above, compounds having structures of Formulae 7 to 10 have excellent electron transport properties and excellent hole-blocking properties. Therefore, HBL1 850 can function as both a hole-blocking layer and an electron transport layer.

[0204] In an exemplary aspect, EML2 940 can emit yellow-green (YG) light. For example, EML2 940 can include a yellow-green (YG) dopant 943 and a host 945.

[0205] The host 945 in the EML2 940 may include, but is not limited to, 9,9'-diphenyl-9H,9'H-3,3'-dicarbazole (BCzPh), CBP, 1,3,5-tris(carbazol-9-yl)benzene (TCP), TCTA, 4,4'-di(carbazol-9-yl)-2,2'-dimethylbiphenyl (CDBP), 2,7-di(carbazol-9-yl)-9,9-dimethylfluorene (DMFL-CBP), 2,2',7,7'-tetra(carbazol-9-yl)-9,9-spirofluorene (spiro-CBP), bis[2-(diphenylphosphine)] phenyl] ether (DPEPO), 4'-(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitrile (PCzB-2CN), 3'-(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitrile (mCzB-2CN), 3,6-bis(carbazol-9-yl)-9-(2-ethyl-hexyl)-9H-carbazole (TCz1), bis(2-hydroxyphenyl)-pyridinium)beryllium (Bepp2), bis(10-hydroxybenzo[h]quinolinium)beryllium (Bebq2) and / or 1,3,5-tri(1-pyrenyl)benzene (TPB3).

[0206] The yellow-green (YG) dopant 943 may include at least one of a yellow-green (YG) fluorescent material, a yellow-green (YG) phosphorescent material, and a yellow-green (YG) delayed fluorescent material. As an example, the yellow-green (YG) dopant 943 may include, but is not limited to, 5,6,11,12-tetraphenylnaphthalene (Rubrene), 2,8-di-tert-butyl-5,11-di(4-tert-butylphenyl)-6,12-diphenyltetracene (TBRb), bis(2-phenylbenzothiazole)(acetylacetonate)iridium(III) (Ir(BT)2(acac)), bis(2-(9,9-diethyl-fluoren-2-yl)-1-phenyl-1H-benzo[d]imidazole)(acetylacetonate)iridium(III) (Ir(fbi)2(acac)), bis(2-phenylpyridine)(3-(pyridin-2-yl)-2H-chromen-2-one)iridium(III) (fac-Ir(ppy)2Pc), bis(2-(2,4-difluorophenyl)quinoline)(picolinic acid)iridium(III) (FPQIrpic), and the like.

[0207] Alternatively, EML2 940 may emit red-green (RG) light. In this case, EML2 940 may include green (G) and red (R) dopants 943 and a host 945. In this case, EML2 940 may have a single-layer structure including a host, a green (G) dopant, and a red (R) dopant, or may have a double-layer structure including a lower layer (first layer) including a host and a green (G) dopant (or a red (R) dopant), and an upper layer (second layer) including a host and a red (R) dopant (or a green (G) dopant).

[0208] The host 945 in the EML2 940 emitting red-green (RG) light may be the same as the host emitting yellow-green (YG) light.

[0209] The green (G) dopant 943 in the EML2 940 may include at least one of a green fluorescent material, a green phosphorescent material, and a green delayed fluorescent material. As examples, the green (G) dopant 943 may include, but is not limited to, [bis(2-phenylpyridine)](pyridine-2-benzofurano[2,3-b]pyridine)iridium, fac-tris(2-phenylpyridine)iridium(III) (fac-Ir(ppy)3), bis(2-phenylpyridine)(acetylacetonate)iridium(III) (Ir(ppy)2(acac)), tris[2-(p-tolyl)pyridine]iridium(III) (Ir(mppy)3), bis(2-(naphthalene-2-yl)pyridine)(acetylacetonate)iridium(III) (Ir(npy)2acac), tris(2-phenyl-3-methyl-pyridine)iridium (Ir(3mppy)3), fac-tris(2-(3-p-xylyl)phenyl)pyridineiridium(III) (TEG), and the like.

[0210] The red (R) dopant 943 in the EML2 940 may include at least one of a red fluorescent material, a red phosphorescent material, and a red delayed fluorescent material. As examples, the red (R) dopant 943 may include, but is not limited to, [bis(2-(4,6-dimethyl)phenylquinoline)](2,2,6,6-tetramethylheptene-3,5-dione)iridium(III), bis[2-(4-n-hexylphenyl)quinoline](acetylacetonate)iridium(III) (Hex-Ir(phq)2(acac)), tris[2-(4-n-hexylphenyl)quinoline]iridium(III) (Hex-Ir(phq)3), tris[2-phenyl-4-methylquinoline]iridium(III) (Ir(Mphq)3), bis(2-phenylquinoline)(2,2,6,6-tetramethylheptene-3,5-dione)iridium(III) (Ir(dpm)PQ2), bis(phenylisoquinoline)(2,2,6,6-tetramethylheptene-3,5-dione)iridium(III) (Ir(dpm)PQ2), (dmpq)3), bis[2-(2-methylphenyl)-7-methyl-quinolinol]iridium(III) (Ir(dmpq)2(acac)), bis[2-(3,5-dimethylphenyl)-4-methyl-quinolinol](acetylacetonate)iridium(III) (Ir(mphmq)2(acac)), etc.

[0211] In an alternative aspect, EML2 940 can have a three-layer structure, with a first layer including a host and a red (R) dopant, a second layer including a host and a yellow-green (YG) dopant, and a third layer including a host and a green (G) dopant.

[0212] When the EML2 940 emits red-green (RG) or yellow-green (YG) light, the content of the host 945 may be about 70 wt% to about 99.9 wt%, and the content of the dopant 943 may be about 0.01 wt% to about 30 wt% in the EML2 940. For example, the content of the dopant 943 in the EML2 940 may be about 0.1 wt% to about 10 wt%, for example, about 1 wt% to about 5 wt%, so that the EML2 940 can achieve sufficient luminous efficiency and luminous lifetime.

[0213] Each of ETL1 and ETL2 950 can independently include an oxazole compound, a triazole compound, a phenanthroline compound, a benzoxazole compound, a benzothiazole compound, a benzimidazole compound, a triazine compound, etc. For example, each of ETL1 and ETL2 950 can independently include an electron transport material selected from, but not limited to, the following: Alq3, PBD, spiro-PBD, Liq, TPBi, BAlq, Bphen, NBphen, BCP, TAZ, NTAZ, TpPyPB, TmPPPyTz, PFNBr, TPQ, TSPO1, ZADN, 1,3-bis(9-phenyl-1,10-phenanthroline-2-yl)benzene, p-bPPhenB, m-bPPhenB, and combinations thereof.

[0214] The EBL2, which may be disposed between the HTL2 920 and the EML2 940, may include a second electron blocking material. As an example, the second electron blocking material may include an amine compound having a structure of Formulas 5 to 6.

[0215] Alternatively, EBL2 may include, but is not limited to, TCTA, tris[4-(diethylamino)phenyl]amine, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, TAPC, MTDATA, 1,3-di(carbazol-9-yl)benzene (mCP), 3,3-di(9H-carbazol-9-yl)biphenyl (mCBP), CuPc, DNTPD, TDAPB, DCDPA, 2,8-bis(9-phenyl-9H-carbazol-3-yl)dibenzo[b,d]thiophene, 3,6-bis(N-carbazyl)-N-phenyl-carbazole, and combinations thereof.

[0216] The HBL2, which may be disposed between the EML2 940 and the ETL2 960, may include a second hole blocking material. As an example, the second hole blocking material may include an azine compound having a structure of Formulae 7 to 8 and / or a benzimidazole compound having a structure of Formulae 9 to 10. Alternatively, the HBL2 may include an oxadiazole compound, a triazole compound, a phenanthroline compound, a benzoxazole compound, a benzothiazole compound, a benzimidazole compound, a triazine compound, or the like, which may be used as an electron transport material in the ETL2 950.

[0217] In OLED D3, EML1 840 includes a dopant 842 of a boron-based compound and a host 844 of an anthracene-based compound in which at least one protium is substituted with deuterium, and EML2 940 emits red-green (RG) and / or yellow-green (YG) light. Alternatively, EML1 840 may emit red-green (RG) and / or yellow-green light, and EML2 940 may include a dopant 842 of a boron-based compound and a host 844 of an anthracene-based compound to emit blue (B) light.

[0218] In OLED D3, EML1 840 includes a boron-based compound dopant 842 and a host 844 of an at least partially deuterated anthracene-based compound. Boron-based compound dopant 842 can have an asymmetric chemical structure as shown in Formula 1B and can be undeuterated or partially deuterated. Furthermore, host 844 of anthracene-based compound can have a structure in which two naphthyl moieties are directly or via a linker connected to an anthracene moiety, and at least one protium (e.g., all protium) is deuterated. Consequently, OLED D3 and organic light-emitting display device 600 can improve their luminous efficiency and luminous lifetime.

[0219] In addition, the OLED D3 and the organic light-emitting display device 600 can maximize their luminous efficiency and luminous lifetime by applying the arylamine compounds having the structures of Formula 5 and Formula 6 as the first electron blocking material 832 to the EBL1 830, and optionally applying the azine compounds having the structures of Formula 7 to Formula 8 and / or the benzimidazole compounds having the structures of Formula 9 to Formula 10 as the first hole blocking layer 852 to the HBL1 850.

[0220] Alternatively, the organic light emitting diode may have three or more light emitting parts. Figure 7 is a schematic cross-sectional view illustrating an organic light emitting diode according to another exemplary aspect of the present disclosure. Figure 7As shown, the organic light emitting diode (OLED) D4 includes a first electrode 710 and a second electrode 720 facing each other, and a light emitting layer 730A disposed between the first electrode 710 and the second electrode 720. The light emitting layer 730A includes a first light emitting portion 1000 disposed between the first electrode 710 and the second electrode 720, a second light emitting portion 1100 disposed between the first light emitting portion 1000 and the second electrode 720, a third light emitting portion 1200 disposed between the second light emitting portion 1100 and the second electrode 720, a first charge generation layer (CGL1) 1070 disposed between the first light emitting portion 1000 and the second light emitting portion 1100, and a second charge generation layer (CGL2) 1170 disposed between the second light emitting portion 1100 and the third light emitting portion 1200.

[0221] At least one of the first to third light-emitting portions 1000, 1100, and 1200 may emit blue (B) light, and at least another of the first to third light-emitting portions 1000, 1100, and 1200 may emit red-green (RG) or yellow-green (YG) light. OLED D4 will be described in detail below, in which the first and third light-emitting portions 1000 and 1200 emit blue (B) light, and the second light-emitting portion 1100 emits red-green (RG) and / or yellow-green (YG) light.

[0222] The first light-emitting portion 1000 includes an EML1 1040 disposed between the first electrode 710 and the CGL1 1070. The first light-emitting portion 1000 may include an EBL1 1030 disposed between the first electrode 710 and the EML1 1040, and optionally, an HBL1 1050 disposed between the EML1 1040 and the CGL1 1070. In addition, the first light-emitting portion 1000 may further include a HIL 1010 disposed between the first electrode 710 and the EBL1 1030, an HTL1 1020 disposed between the HIL 1010 and the EBL1 1030, and optionally, a first electron transport layer (ETL1) disposed between the HBL1 1050 and the CGL1 1070.

[0223] The second light emitting portion 1100 includes an EML2 1140 disposed between the CGL1 1070 and the CGL2 1170. The second light emitting portion 1100 may include an HTL2 1120 disposed between the CGL1 1070 and the EML2 1140, and an ETL2 1150 disposed between the EML2 1140 and the CGL2 1170. In addition, the second light emitting portion 1100 may further include an EBL2 disposed between the HTL2 1120 and the EML2 1140, and / or an HBL2 disposed between the EML2 1140 and the ETL2 1150.

[0224] The third light-emitting portion 1200 includes a third light-emitting material layer (EML3) 1240 disposed between the CGL2 1170 and the second electrode 720. The third light-emitting portion 1200 may include a third electron blocking layer (EBL3) 1230 disposed between the CGL2 1170 and the EML3 1240, and optionally a third hole blocking layer (HBL3) 1250 disposed between the EML3 1240 and the second electrode 720. In addition, the third light-emitting portion 1200 may further include a third hole transport layer (HTL3) 1220 disposed between the CGL2 1170 and the EBL3 1230, an EIL 1260 disposed between the HBL3 1250 and the second electrode 720, and optionally a third electron transport layer (ETL3) disposed between the HBL3 1250 and the EIL 1260.

[0225] CGL1 1070 is provided between the first light-emitting portion 1000 and the second light-emitting portion 1100. CGL1 1070 may be a PN junction CGL having a first N-type CGL (N-CGL1) 1080 and a first P-type CGL (P-CGL1) 1090. N-CGL1 1080 is disposed between HBL1 1050 and HTL2 1120, and P-CGL1 1090 is disposed between N-CGL1 1080 and HTL2 1120. N-CGL1 1080 injects electrons into the first light-emitting portion 1000, and P-CGL1 1090 injects holes into the second light-emitting portion 1100.

[0226] CGL2 1170 is disposed between the second light-emitting portion 1100 and the third light-emitting portion 1200. CGL2 1170 may be a PN junction CGL having a second N-type CGL (N-CGL2) 1180 and a second P-type CGL (P-CGL2) 1190. N-CGL2 1180 is disposed between ETL2 1150 and HTL3 1220, and P-CGL2 1190 is disposed between N-CGL2 1180 and HTL3 1220. N-CGL2 1180 injects electrons into the second light-emitting portion 1100, and P-CGL2 1190 injects holes into the third light-emitting portion 1200.

[0227] Each of the HIL 1010, HTL1 1020, HTL2 1120, HTL3 1130, EIL 120, CGL1 1070, and CGL2 1170 may independently include the same materials as described above. Each of the HTL1 1020, HTL2 1120, and HTL3 1220 may include the same material or different materials from each other. Furthermore, the CGL1 1070 may include the same material as or different materials from the CGL2 1170.

[0228] EML1 1040 includes a first dopant 1042 of a boron-based compound and a first host 1044 of an anthracene-based compound, thereby emitting blue (B) light. EML3 1240 includes a second dopant 1242 of a boron-based compound and a second host 1244 of anthracene-based compound, thereby emitting blue (B) light.

[0229] The first dopant 1042 and the second dopant 1242 of the boron-based compound may each be undeuterated or partially deuterated and may independently have the structures of Formulas 1A to 2. The first host 1044 and the second host 1244 of the anthracene-based compound may each be at least partially deuterated and may independently have the structures of Formulas 3 to 4. The first dopant 1042 may be the same as or different from the second dopant 1242, and the first host 1044 may be the same as or different from the second host 1244.

[0230] In one exemplary embodiment, the first host 1044 and the second host 1244 may each independently contain about 70 wt% to about 99.9 wt%, and the first dopant 1042 and the second dopant 1242 may each independently contain about 0.1 wt% to about 30 wt% in EML1 1040 and EML3 1240, respectively. For example, the first dopant 1042 and the second dopant 1242 may each contain about 0.1 wt% to about 10 wt%, for example, about 1 wt% to about 5 wt%, in EML1 1040 and EML3 1240, respectively, so that both EML1 1040 and EML3 1240 can achieve sufficient luminous efficiency and luminous lifetime.

[0231] Each of EBL1 1030 and EBL3 1230 can prevent electrons from being transferred from EML1 1040 or EML3 1240 to the first electrode 710 or CGL2 1170, respectively. Each of EBL1 1030 and EBL3 1230 can include a first electron blocking material 1032 and a third electron blocking material 1232, respectively. The first electron blocking material 1032 and the third electron blocking material 1232 can each independently include an amine compound having a structure of Formulae 5 to 6. The first electron blocking material 1032 can be the same as or different from the third electron blocking material 1232.

[0232] HBL1 1050 and HBL3 1250 each prevent holes from being transferred from EML1 1040 or EML3 1240 to CGL1 1070 or the second electrode 720. HBL1 1050 and HBL3 1250 each may include a first hole blocking material 1052 and a third hole blocking material 1252, respectively. The first hole blocking material 1052 and the third hole blocking material 1252 each may independently include an azine compound having a structure of Formulae 7 to 8 and / or a benzimidazole compound having a structure of Formulae 9 to 10. The first hole blocking material 1052 may be the same as or different from the third hole blocking material 1252.

[0233] As described above, the compounds having the structures of Formulae 7 to 10 have excellent electron transport properties and excellent hole blocking properties. Therefore, HBL1 1050 and HBL3 1250 can each serve as a hole blocking layer and an electron transport layer.

[0234] In one exemplary aspect, the EML2 1140 can emit yellow-green (YG) light. For example, the EML2 1140 can include a yellow-green (YG) dopant 1143 and a host 1145.

[0235] Alternatively, the EML2 1140 may emit red-green (RG) light and may include a red (R) dopant, a green (G) dopant 1143, and a host 1145. In this case, the EML2 1140 may have a single-layer structure including a host, a green (G) dopant, and a red (R) dopant, or may have a double-layer structure including a lower layer (first layer) including a host and a green (G) dopant (or a red (R) dopant) and an upper layer (second layer) including a host and a red (R) dopant (or a green (G) dopant).

[0236] In an alternative aspect, EML2 1140 may have a three-layer structure: a first layer includes a host and a red (R) dopant, a second layer includes a host and a yellow-green (YG) dopant, and a third layer includes a host and a green (G) dopant. The dopant 1143 and host 1145 in EML2 1140 may be the same as those described above. Figure 6 The corresponding materials described are the same.

[0237] Each of the ETL1, the ETL2 1150, the ETL3, the EBL2 disposed between the HTL2 1120 and the EML2 1140, and the HBL2 disposed between the EML2 1140 and the ETL2 1150 may include the same compounds as the corresponding materials described above.

[0238] Each of EML1 1040 and EML3 1240 includes a first dopant 1042 and a second dopant 1242 of a boron-based compound, and a first host 1044 and a second host 1244 of an anthracene-based compound in which at least one carbon atom is deuterated. The first dopant 1042 and the second dopant 1242 of the boron-based compound can each independently have an asymmetric chemical structure as shown in Formula 1B and can be undeuterated or partially deuterated. In addition, the first host 1044 and the second host 1244 of the anthracene-based compound can each have a structure in which two naphthyl moieties are directly or via a linker connected to an anthracene moiety, and at least one protium (e.g., all protium) is deuterated. As a result, the OLED D4 and the organic light-emitting display device 600 can improve their luminous efficiency and luminous lifespan.

[0239] Furthermore, by using arylamine compounds having structures of Formulae 5 and 6 as the first electron-blocking material 1032 and the third electron-blocking material 1232 in EBL1 1030 and EBL3 1230, respectively, and optionally using azine compounds having structures of Formulae 7 to 8 and / or benzimidazole compounds having structures of Formulae 9 to 10 as the first hole-blocking material 1052 and the third hole-blocking material 1252 in HBL1 1050 and HBL3 1250, respectively, OLED D4 and organic light-emitting display device 600 can maximize their luminous efficiency and luminous lifetime. Furthermore, OLED D4 includes a first light-emitting portion 1000 and a third light-emitting portion 1020, each emitting blue (B) light, and a second light-emitting portion 1100 emitting yellow-green (YG) or red-green (RG) light, thereby emitting white (W) light.

[0240] exist Figure 7 , depicts an OLED D4 having a series structure of three light-emitting sections. Alternatively, the OLED may further include at least one other light-emitting section and at least one other charge generation layer.

[0241] In addition, the organic light-emitting device of the present disclosure may include a color conversion layer. Figure 8 is a schematic cross-sectional view illustrating an organic light emitting display device in another exemplary embodiment of the present disclosure.

[0242] like Figure 8As shown, the organic light emitting display device 1300 includes a first substrate 1302 (which defines a red pixel area RP, a green pixel area GP, and a blue pixel area BP), a second substrate 1304 facing the first substrate 1302, a thin film transistor Tr above the first substrate 1302, an organic light emitting diode (OLED) D arranged between the first substrate 1302 and the second substrate 1304 and emitting blue (B) light, and a color conversion layer 1380 arranged between the OLED D and the second substrate 1304. Figure 8 Although not shown, a color filter layer may be disposed between the second substrate 1304 and each color conversion layer 1380 .

[0243] Thin film transistors Tr are arranged on the first substrate 1302, corresponding to the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP. A passivation layer 1360 is formed on the entire first substrate 1302, covering the thin film transistors Tr. The passivation layer 1360 has a drain contact hole 1362, exposing one electrode (e.g., the drain) of the thin film transistor Tr.

[0244] An OLED D including a first electrode 1410, a light emitting layer 1430, and a second electrode 1420 is disposed on the passivation layer 1360. The first electrode 1410 can be connected to the drain of the thin film transistor Tr through a drain contact hole 1362. In addition, a bank layer 1364 covering the edge of the first electrode 1410 is formed on the boundary between the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP. In this case, the OLED D may have Figure 3 or Figure 4 The OLED D is arranged in the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP to provide blue (B) light.

[0245] Color conversion layer 1380 may include a first color conversion layer 1382 corresponding to the red pixel region RP and a second color conversion layer 1384 corresponding to the green pixel region GP. As an example, color conversion layer 1380 may include an inorganic light emitting material such as quantum dots (QD).

[0246] Blue (B) light emitted from the OLED D in the red pixel region RP is converted into red (R) light by the first color conversion layer 1382, while blue (B) light emitted from the OLED D in the green pixel region GP is converted into green (G) light by the second color conversion layer 1384. Therefore, the organic light-emitting display device 1300 can realize a color image.

[0247] In addition, when light emitted from the OLED D is displayed through the first substrate 1302 , a color conversion layer 1380 may be disposed between the OLED D and the first substrate 1302 .

[0248] Synthesis Example 1: Synthesis of Compound 1-1

[0249] (1) Synthesis of intermediate 1-1C

[0250] [Reaction formula 1-1]

[0251]

[0252] Compound 1-1A (69.2 g, 98 mmol), compound 1-1B (27.6 g, 98 mmol), palladium acetate (0.45 g, 2 mmol), sodium tert-butoxide (18.9 g, 196 mmol), tri-tert-butylphosphine (0.8 g, 4 mmol) and toluene (300 ml) were placed in a 500 ml reaction vessel, and the solution was refluxed under stirring for 5 hours. After the reaction was completed, the solution was filtered and the filtrate was concentrated. The crude product was purified by column chromatography to obtain intermediate 1-1C (58.1 g, yield: 84%).

[0253] (2) Synthesis of compound 1-1

[0254] [Reaction formula 1-2]

[0255]

[0256] Intermediate 1-1C (11.9 g, 12.5 mmol) and tert-butylbenzene (60 ml) were placed in a 500 ml reaction vessel. n-Butyl lithium (45 ml, 37.5 mmol) was added dropwise to the reaction vessel at -78°C, and the solution was stirred at 60°C for 3 hours. Nitrogen was blown into the reaction vessel at 60°C to remove by-products, and boron tribromide (6.3 g, 25 mmol) was added dropwise to the solution at -78°C, and the solution was stirred at room temperature (RT) for 1 hour. N,N-diisopropylethylamine (3.2 g, 25 mmol) was added dropwise to the solution at 0°C, and the solution was stirred at 120°C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added to the reaction vessel at RT, and the solution was stirred. The organic layer was extracted with ethyl acetate and concentrated, and the crude product was purified by column chromatography to obtain compound 1-1 (2.3 g, yield: 20%).

[0257] Synthesis Example 2: Synthesis of Compound 1-4

[0258] (1) Synthesis of intermediate 1-4C

[0259] [Reaction formula 2-1]

[0260]

[0261] Compound 1-4A (43.1 g, 98 mmol), compound 1-4B (27.6 g, 98 mmol), palladium acetate (0.45 g, 2 mmol), sodium tert-butoxide (18.9 g, 196 mmol), tri-tert-butylphosphine (0.8 g, 4 mmol) and toluene (300 ml) were placed in a 500 ml reaction vessel, and the solution was refluxed under stirring for 5 hours. After the reaction was completed, the solution was filtered and the filtrate was concentrated. The crude product was purified by column chromatography to obtain intermediate 1-4C (57.1 g, yield: 85%).

[0262] (2) Synthesis of Compounds 1-4

[0263] [Reaction formula 2-2]

[0264]

[0265] Intermediate 1-4C (8.6 g, 12.5 mmol) and tert-butylbenzene (60 ml) were placed in a 500 ml reaction vessel. n-Butyl lithium (45 ml, 37.5 mmol) was added dropwise to the reaction vessel at -78°C, and the solution was stirred at 60°C for 3 hours. Nitrogen was blown into the reaction vessel at 60°C to remove by-products, and boron tribromide (6.3 g, 25 mmol) was added dropwise to the solution at -78°C, and the solution was stirred at room temperature (RT) for 1 hour. N,N-diisopropylethylamine (3.2 g, 25 mmol) was added dropwise to the solution at 0°C, and the solution was stirred at 120°C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added to the reaction vessel at RT, and the solution was stirred. The organic layer was extracted with ethyl acetate and concentrated, and the crude product was purified by column chromatography to obtain compound 1-4 (1.9 g, yield: 23%).

[0266] Synthesis Example 3: Synthesis of Compound 1-6

[0267] (1) Synthesis of intermediate 1-6C

[0268] [Reaction formula 3-1]

[0269]

[0270] Compound 1-6A (58.9 g, 98 mmol), compound 1-6B (33.2 g, 98 mmol), palladium acetate (0.45 g, 2 mmol), sodium tert-butoxide (18.9 g, 196 mmol), tri-tert-butylphosphine (0.8 g, 4 mmol) and toluene (300 ml) were placed in a 500 ml reaction vessel, and the solution was refluxed under stirring for 5 hours. After the reaction was completed, the solution was filtered and the filtrate was concentrated. The crude product was purified by column chromatography to obtain intermediate 1-6C (59.7 g, yield: 75%).

[0271] (2) Synthesis of Compounds 1-6

[0272] [Reaction formula 3-2]

[0273]

[0274] Intermediate 1-6C (10.1 g, 12.5 mmol) and tert-butylbenzene (60 ml) were placed in a 500 ml reaction vessel. n-Butyl lithium (45 ml, 37.5 mmol) was added dropwise to the reaction vessel at -78°C, and the solution was stirred at 60°C for 3 hours. Nitrogen was blown into the reaction vessel at 60°C to remove by-products, and boron tribromide (6.3 g, 25 mmol) was added dropwise to the solution at -78°C, and the solution was stirred at room temperature (RT) for 1 hour. N,N-diisopropylethylamine (3.2 g, 25 mmol) was added dropwise to the solution at 0°C, and the solution was stirred at 120°C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added to the reaction vessel at RT, and the solution was stirred. The organic layer was extracted with ethyl acetate and concentrated, and the crude product was purified by column chromatography to obtain compound 1-6 (1.9 g, yield: 21%).

[0275] Synthesis Example 4: Synthesis of Compound 1-8

[0276] (1) Synthesis of intermediate 1-8C

[0277] [Reaction formula 4-1]

[0278]

[0279] Compound 1-8A (33.0 g, 98 mmol), compound 1-8B (45.7 g, 98 mmol), palladium acetate (0.45 g, 2 mmol), sodium tert-butoxide (18.9 g, 196 mmol), tri-tert-butylphosphine (0.8 g, 4 mmol) and toluene (300 ml) were placed in a 500 ml reaction vessel, and the solution was refluxed under stirring for 5 hours. After the reaction was completed, the solution was filtered and the filtrate was concentrated. The crude product was purified by column chromatography to obtain intermediate 1-8C (54.1 g, yield: 72%).

[0280] (2) Synthesis of Compounds 1-8

[0281] [Reaction Formula 4-2]

[0282]

[0283] Intermediate 1-8C (9.6 g, 12.5 mmol) and tert-butylbenzene (60 ml) were placed in a 500 ml reaction vessel. n-Butyllithium (45 ml, 37.5 mmol) was added dropwise to the reaction vessel at -78°C, and the solution was stirred at 60°C for 3 hours. Nitrogen was blown into the reaction vessel at 60°C to remove byproducts. Boron tribromide (6.3 g, 25 mmol) was added dropwise to the solution at -78°C, and the solution was stirred at room temperature (RT) for 1 hour. N,N-Diisopropylethylamine (3.2 g, 25 mmol) was added dropwise to the solution at 0°C, and the solution was stirred at 120°C for 2 hours. After the reaction was completed, aqueous sodium acetate was added to the reaction vessel at RT, and the solution was stirred. The organic layer was extracted with ethyl acetate and concentrated, and the crude product was purified by column chromatography to obtain Compound 1-8 (2.0 g, 21% yield).

[0284] Synthesis Example 5: Synthesis of Compound 1-11

[0285] (1) Synthesis of intermediate 1-11C

[0286] [Reaction Formula 5-1]

[0287]

[0288] Compound 1-11A (28.4 g, 98 mmol), compound 1-11B (52.0 g, 98 mmol), palladium acetate (0.45 g, 2 mmol), sodium tert-butoxide (18.9 g, 196 mmol), tri-tert-butylphosphine (0.8 g, 4 mmol) and toluene (300 ml) were placed in a 500 ml reaction vessel, and the solution was then refluxed under stirring for 5 hours. After the reaction was complete, the solution was filtered and the filtrate was concentrated. The crude product was purified by column chromatography to obtain intermediate 1-11C (39.9 g, yield: 52%).

[0289] (2) Synthesis of Compounds 1-11

[0290] [Reaction Formula 5-2]

[0291]

[0292] Intermediate 1-11C (9.8 g, 12.5 mmol) and tert-butylbenzene (60 ml) were placed in a 500 ml reaction vessel. n-Butyl lithium (45 ml, 37.5 mmol) was added dropwise to the reaction vessel at -78°C, and the solution was stirred at 60°C for 3 hours. Nitrogen was blown into the reaction vessel at 60°C to remove by-products, and boron tribromide (6.3 g, 25 mmol) was added dropwise to the solution at -78°C, and the solution was stirred at room temperature (RT) for 1 hour. N,N-diisopropylethylamine (3.2 g, 25 mmol) was added dropwise to the solution at 0°C, and the solution was stirred at 120°C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added to the reaction vessel at RT, and the solution was stirred. The organic layer was extracted with ethyl acetate and concentrated, and the crude product was purified by column chromatography to obtain compound 1-11 (1.4 g, yield: 15%).

[0293] Synthesis Example 6: Synthesis of Compound 1-12

[0294] (1) Synthesis of intermediate 1-12C

[0295] [Reaction formula 6-1]

[0296]

[0297] Compound 1-12A (28.0 g, 98 mmol), compound 1-12B (51.6 g, 98 mmol), palladium acetate (0.45 g, 2 mmol), sodium tert-butoxide (18.9 g, 196 mmol), tri-tert-butylphosphine (0.8 g, 4 mmol), and toluene (300 ml) were placed in a 500 ml reaction vessel, and the solution was refluxed under stirring for 5 hours. After the reaction was completed, the solution was filtered, and the filtrate was concentrated. The crude product was purified by column chromatography to obtain intermediate 1-12C (44.1 g, yield: 58%).

[0298] (2) Synthesis of Compounds 1-12

[0299] [Reaction formula 6-2]

[0300]

[0301] Intermediate 1-12C (9.7 g, 12.5 mmol) and tert-butylbenzene (60 ml) were placed in a 500 ml reaction vessel. n-Butyl lithium (45 ml, 37.5 mmol) was added dropwise to the reaction vessel at -78°C, and the solution was stirred at 60°C for 3 hours. Nitrogen was blown into the reaction vessel at 60°C to remove by-products, and boron tribromide (6.3 g, 25 mmol) was added dropwise to the solution at -78°C, and the solution was stirred at room temperature (RT) for 1 hour. N,N-diisopropylethylamine (3.2 g, 25 mmol) was added dropwise to the solution at 0°C, and the solution was stirred at 120°C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added to the reaction vessel at RT, and the solution was stirred. The organic layer was extracted with ethyl acetate and concentrated, and the crude product was purified by column chromatography to obtain compound 1-12 (1.7 g, yield: 18%).

[0302] Synthesis Example 7: Synthesis of Compound 1-13

[0303] (1) Synthesis of intermediate 1-13C

[0304] [Reaction Formula 7-1]

[0305]

[0306] Compound 1-13A (34.8 g, 98 mmol), compound 1-13B (46.6 g, 98 mmol), palladium acetate (0.45 g, 2 mmol), sodium tert-butoxide (18.9 g, 196 mmol), tri-tert-butylphosphine (0.8 g, 4 mmol), and toluene (300 ml) were placed in a 500 ml reaction vessel, and the solution was refluxed under stirring for 5 hours. After the reaction was completed, the solution was filtered, and the filtrate was concentrated. The crude product was purified by column chromatography to obtain intermediate 1-13C (41.3 g, yield: 53%).

[0307] (2) Synthesis of Compounds 1-13

[0308] [Reaction Formula 7-2]

[0309]

[0310] Intermediate 1-13C (9.9 g, 12.5 mmol) and tert-butylbenzene (60 ml) were placed in a 500 ml reaction vessel. n-Butyl lithium (45 ml, 37.5 mmol) was added dropwise to the reaction vessel at -78°C, and the solution was stirred at 60°C for 3 hours. Nitrogen was blown into the reaction vessel at 60°C to remove by-products, and boron tribromide (6.3 g, 25 mmol) was added dropwise to the solution at -78°C, and the solution was stirred at room temperature (RT) for 1 hour. N,N-diisopropylethylamine (3.2 g, 25 mmol) was added dropwise to the solution at 0°C, and the solution was stirred at 120°C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added to the reaction vessel at RT, and the solution was stirred. The organic layer was extracted with ethyl acetate and concentrated, and the crude product was purified by column chromatography to obtain compound 1-13 (1.4 g, yield: 15%).

[0311] Synthesis Example 8: Synthesis of Compound 1-17

[0312] (1) Synthesis of intermediate 1-17C

[0313] [Reaction formula 8-1]

[0314]

[0315] Compound 1-17A (33.4 g, 98 mmol), compound 1-17B (46.1 g, 98 mmol), palladium acetate (0.45 g, 2 mmol), sodium tert-butoxide (18.9 g, 196 mmol), tri-tert-butylphosphine (0.8 g, 4 mmol), and toluene (300 ml) were placed in a 500 ml reaction vessel, and the solution was refluxed under stirring for 5 hours. After the reaction was completed, the solution was filtered, and the filtrate was concentrated. The crude product was purified by column chromatography to obtain intermediate 1-17C (47.1 g, yield: 62%).

[0316] (2) Synthesis of Compounds 1-17

[0317] [Reaction formula 8-2]

[0318]

[0319] Intermediate 1-17C (9.7 g, 12.5 mmol) and tert-butylbenzene (60 ml) were placed in a 500 ml reaction vessel. n-Butyl lithium (45 ml, 37.5 mmol) was added dropwise to the reaction vessel at -78°C, and the solution was stirred at 60°C for 3 hours. Nitrogen was blown into the reaction vessel at 60°C to remove by-products, and boron tribromide (6.3 g, 25 mmol) was added dropwise to the solution at -78°C, and the solution was stirred at room temperature (RT) for 1 hour. N,N-diisopropylethylamine (3.2 g, 25 mmol) was added dropwise to the solution at 0°C, and the solution was stirred at 120°C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added to the reaction vessel at RT, and the solution was stirred. The organic layer was extracted with ethyl acetate and concentrated, and the crude product was purified by column chromatography to obtain compound 1-17 (1.6 g, yield: 17%).

[0320] Synthesis Example 9: Synthesis of Compound 2-1

[0321] [Reaction formula 9]

[0322]

[0323] Compound 2-1A (2.0 g, 5.2 mmol), compound 2-1B (1.5 g, 5.7 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.24 g, 0.26 mmol) and toluene (50 ml) were placed in a 250 ml reaction vessel in a drying oven. The reaction vessel was taken out of the drying oven, and anhydrous sodium carbonate (2 M, 20 ml) was added to the solution. The reactants were stirred and heated at 90°C overnight. The reaction was monitored by HPLC (high performance liquid chromatography). After the solution was cooled to RT, the organic layer was separated. The aqueous layer was washed with dichloromethane, and the organic layer was concentrated by rotary evaporation to obtain a gray powder. The gray powder was purified with alumina, precipitated with hexane, and purified by silica gel column chromatography to obtain compound 2-1 (2.3 g, yield: 86%) as a white powder.

[0324] Synthesis Example 10: Synthesis of Compound 2-2

[0325] [Reaction formula 10]

[0326]

[0327] Compound 2-2A (2.0 g, 5.2 mmol), compound 2-2B (1.5 g, 5.7 mmol), Pd2(dba)3 (0.24 g, 0.26 mmol) and toluene (50 ml) were placed in a 250 ml reaction vessel in a drying oven. The reaction vessel was removed from the drying oven, and anhydrous sodium carbonate (2 M, 20 ml) was added to the solution. The reactants were stirred and heated at 90° C. overnight. The reaction was monitored by HPLC. After the solution was cooled to RT, the organic layer was separated. The aqueous layer was washed with dichloromethane, and the organic layer was concentrated by rotary evaporation to obtain a gray powder. The gray powder was purified with alumina, precipitated with hexane, and purified by silica gel column chromatography to obtain compound 2-2 (2.0 g, yield: 89%) as a white powder.

[0328] Synthesis Example 11: Synthesis of Compound 2-3

[0329] [Reaction formula 11]

[0330]

[0331] Compound 2-3A (2.0 g, 6.0 mmol), compound 2-3B (1.9 g, 6.6 mmol), Pd2(dba)3 (0.3 g, 0.3 mmol) and toluene (50 ml) were placed in a 250 ml reaction vessel in a drying oven. The reaction vessel was removed from the drying oven, and anhydrous sodium carbonate (2 M, 20 ml) was added to the solution. The reactants were stirred and heated at 90°C overnight. The reaction was monitored by HPLC. After the solution was cooled to RT, the organic layer was separated. The aqueous layer was washed with dichloromethane, and the organic layer was concentrated by rotary evaporation to obtain a gray powder. The gray powder was purified with alumina, precipitated with hexane, and purified by silica gel column chromatography to obtain compound 2-3 (2.0 g, yield: 79%) as a white powder.

[0332] Synthesis Example 12: Synthesis of Compound 2-4

[0333] [Reaction formula 12]

[0334]

[0335] Compound 2-4A (2.0 g, 6.0 mmol), compound 2-4B (2.4 g, 6.6 mmol), Pd2(dba)3 (0.3 g, 0.3 mmol) and toluene (50 ml) were placed in a 250 ml reaction vessel in a drying oven. The reaction vessel was removed from the drying oven, and anhydrous sodium carbonate (2 M, 20 ml) was added to the solution. The reactants were stirred and heated at 90° C. overnight. The reaction was monitored by HPLC. After the solution was cooled to RT, the organic layer was separated. The aqueous layer was washed with dichloromethane, and the organic layer was concentrated by rotary evaporation to obtain a gray powder. The gray powder was purified with alumina, precipitated with hexane, and purified by silica gel column chromatography to obtain compound 2-4 (2.0 g, yield: 67%) as a white powder.

[0336] Synthesis Example 13: Synthesis of Compound 2-5

[0337] [Reaction formula 13]

[0338]

[0339] Compound 2-5A (2.0 g, 5.2 mmol), compound 2-5B (2.0 g, 5.7 mmol), Pd2(dba)3 (0.24 g, 0.26 mmol) and toluene (50 ml) were placed in a 250 ml reaction vessel in a drying oven. The reaction vessel was removed from the drying oven, and anhydrous sodium carbonate (2 M, 20 ml) was added to the solution. The reactants were stirred and heated at 90° C. overnight. The reaction was monitored by HPLC. After the solution was cooled to RT, the organic layer was separated. The aqueous layer was washed with dichloromethane, and the organic layer was concentrated by rotary evaporation to obtain a gray powder. The gray powder was purified with alumina, precipitated with hexane, and purified by silica gel column chromatography to obtain compound 2-5 (2.0 g, yield: 81%) as a white powder.

[0340] Synthesis Example 14: Synthesis of Compound 2-6

[0341] [Reaction formula 14]

[0342]

[0343] Compound 2-6A (2.0 g, 5.2 mmol), compound 2-6B (2.0 g, 5.7 mmol), Pd2(dba)3 (0.24 g, 0.26 mmol) and toluene (50 ml) were placed in a 250 ml reaction vessel in a drying oven. The reaction vessel was removed from the drying oven, and anhydrous sodium carbonate (2 M, 20 ml) was added to the solution. The reactants were stirred and heated at 90° C. overnight. The reaction was monitored by HPLC. After the solution was cooled to RT, the organic layer was separated. The aqueous layer was washed with dichloromethane, and the organic layer was concentrated by rotary evaporation to obtain a gray powder. The gray powder was purified with alumina, precipitated with hexane, and purified by silica gel column chromatography to obtain compound 2-6 (2.0 g, yield: 81%) as a white powder.

[0344] Synthesis Example 15: Synthesis of Compound 2-7

[0345] [Reaction formula 15]

[0346]

[0347] Aluminum chloride (0.5 g, 3.6 mmol) was added to a solution of compound 2-1 (5.0 g, 9.9 mmol) dissolved in perdeuterated benzene (100 ml) under a nitrogen atmosphere. The resulting mixture was stirred at RT for 6 hours, and then D2O (50 ml) was added to the mixture. After the organic layer was separated from the aqueous layer, the aqueous layer was washed with dichloromethane (30 ml). The resulting organic layer was dried over MgSO4 and volatile components were removed by rotary evaporation. The crude product was purified by column chromatography to obtain compound 2-7 (4.5 g, yield: 85%) as a white powder.

[0348] Synthesis Example 16: Synthesis of Compound 2-8

[0349] [Reaction formula 16]

[0350]

[0351] Aluminum chloride (0.9 g, 4.3 mmol) was added to a solution of compound 2-2 (5.0 g, 11.6 mmol) dissolved in perdeuterated benzene (120 ml) under a nitrogen atmosphere. The resulting mixture was stirred at RT for 6 hours, and then D2O (70 ml) was added to the mixture. After the organic layer was separated from the aqueous layer, the aqueous layer was washed with dichloromethane (50 ml). The resulting organic layer was dried with MgSO4 and volatile components were removed by rotary evaporation. The crude product was purified by column chromatography to obtain compound 2-8 (4.0 g, yield: 76%) as a white powder.

[0352] Synthesis Example 17: Synthesis of Compound 2-9

[0353] [Reaction 17]

[0354]

[0355] Aluminum chloride (0.9 g, 4.3 mmol) was added to a solution of compound 2-3 (5.0 g, 11.9 mmol) dissolved in perdeuterated benzene (120 ml) under a nitrogen atmosphere. The resulting mixture was stirred at RT for 6 hours, and then D2O (70 ml) was added to the mixture. After the organic layer was separated from the aqueous layer, the aqueous layer was washed with dichloromethane (50 ml). The resulting organic layer was dried with MgSO4 and volatile components were removed by rotary evaporation. The crude product was purified by column chromatography to obtain compound 2-9 (3.0 g, yield: 57%) as a white powder.

[0356] Synthesis Example 18: Synthesis of Compound 2-10

[0357] [Reaction formula 18]

[0358]

[0359] Aluminum chloride (0.9 g, 4.3 mmol) was added to a solution of compound 2-4 (5.0 g, 10.1 mmol) dissolved in perdeuterated benzene (120 ml) under a nitrogen atmosphere. The resulting mixture was stirred at RT for 6 hours, and then D2O (70 ml) was added to the mixture. After the organic layer was separated from the aqueous layer, the aqueous layer was washed with dichloromethane (50 ml). The resulting organic layer was dried over MgSO4 and volatile components were removed by rotary evaporation. The crude product was purified by column chromatography to obtain compound 2-10 (3.5 g, yield: 67%) as a white powder.

[0360] Synthesis Example 19: Synthesis of Compound 2-11

[0361] [Reaction formula 19]

[0362]

[0363] Aluminum chloride (0.9 g, 4.3 mmol) was added to a solution of compound 2-5 (5.0 g, 10.6 mmol) dissolved in perdeuterated benzene (120 ml) under a nitrogen atmosphere. The resulting mixture was stirred at RT for 6 hours, and then D2O (70 ml) was added to the mixture. After the organic layer was separated from the aqueous layer, the aqueous layer was washed with dichloromethane (50 ml). The resulting organic layer was dried over MgSO4 and volatile components were removed by rotary evaporation. The crude product was purified by column chromatography to obtain compound 2-11 (4.0 g, yield: 77%) as a white powder.

[0364] Synthesis Example 20: Synthesis of Compound 2-12

[0365] [Reaction formula 20]

[0366]

[0367] Aluminum chloride (0.9 g, 4.3 mmol) was added to a solution of compound 2-6 (5.0 g, 10.6 mmol) dissolved in deuterated benzene (120 ml) under a nitrogen atmosphere. The resulting mixture was stirred at RT for 6 hours, and then D2O (70 ml) was added to the mixture. After the organic layer was separated from the aqueous layer, the aqueous layer was washed with dichloromethane (50 ml). The resulting organic layer was dried over MgSO4 and volatile components were removed by rotary evaporation. The crude product was purified by column chromatography to obtain compound 2-12 (4.3 g, yield: 82%) as a white powder.

[0368] Manufacturing of Organic Light Emitting Diodes (OLEDs)1

[0369] A glass substrate (40 mm × 40 mm × 0.5 mm) coated with a thin film of ITO was washed with a solvent such as isopropyl alcohol, acetone, and distilled water, ultrasonically cleaned for 5 minutes, and dried in an oven at 100°C. After cleaning the substrate, the substrate was treated with O2 plasma under vacuum for 2 minutes and then transferred to a vacuum chamber for deposition of the light-emitting layer. Subsequently, at about 5 to 7 × 10 - 7 Torr, by evaporation from a heated boat, The light-emitting layer and cathode are deposited in the following order at a deposition rate of:

[0370] HIL (Formula 11 (97 wt%) and Formula 12 (3 wt%), ); HTL (Formula 11, ); EBL (H23 in Formula 6, ); EML (host (H, 98 wt%) and dopant (D, 2 wt%), ); HBL (E1 in formula 8, ); EIL (Formula 13 (98 wt%), Li (2 wt%), ); and cathode (Al, ).

[0371] The OLED is then encapsulated with UV-curable epoxy resin and a moisture-proof agent.

[0372] Comparative Example 1-8 (Ref. 1-8): Production of OLED

[0373] An OLED was manufactured in which the EML contained compound 2-1 as a host and each of compound 1-1 (Ref. 1), compound 1-4 (Ref. 2), compound 1-6 (Ref. 3), compound 1-8 (Ref. 4), compound 1-11 (Ref. 5), compound 1-12 (Ref. 6), compound 1-13 (Ref. 7), and compound 1-17 (Ref. 8) in Formula 3 as dopants, respectively.

[0374] Comparative Examples 9-16 (Ref. 9-16): Fabrication of OLED

[0375] An OLED was manufactured in which the EML contained compound 2-2 as a host and each of compound 1-1 (Ref. 9), compound 1-4 (Ref. 10), compound 1-6 (Ref. 11), compound 1-8 (Ref. 12), compound 1-11 (Ref. 13), compound 1-12 (Ref. 14), compound 1-13 (Ref. 15), and compound 1-17 (Ref. 16) in Formula 3 as dopants, respectively.

[0376] Experimental Example 1: Measurement of OLED Light Emitting Characteristics

[0377] The 9 mm 2 The OLEDs with the same light-emitting area were each connected to an external power supply, and the light-emitting characteristics of all OLEDs were evaluated at room temperature using a constant current source (KEITHLEY) and a photometer PR650. Specifically, at a current density of 10 mA / cm 2 The driving voltage (V), current efficiency (cd / A) and CIE color coordinates at 40°C and a current density of 22.5 mA / m 2 The time it takes for the brightness to drop from the initial brightness to 95% (T 95 ). The measurement results are shown in Table 1 below.

[0378] Table 1: Light-emitting characteristics of OLEDs

[0379] sample dopant main body V EQE (%) CIE(x,y) <![CDATA[T 95 (hr)]]> Ref.1 1-1 2-1 3.99 6.35 (0.140,0.061) 63 Ref.2 1-4 2-1 3.94 6.33 (0.131,0.089) 68 Ref.3 1-6 2-1 3.90 6.61 (0.139,0.074) 88 Ref.4 1-8 2-1 3.88 6.63 (0.137,0.079) 82 Ref.5 1-11 2-1 3.89 6.61 (0.140,0.074) 101 Ref.6 1-12 2-1 3.90 6.59 (0.140,0.073) 95 Ref.7 1-13 2-1 3.91 6.64 (0.137,0.080) 94 Ref.8 1-17 2-1 3.91 6.58 (0.137,0.079) 89 Ref.9 1-1 2-2 4.20 6.24 (0.140,0.060) 69 Ref.10 1-4 2-2 4.20 6.22 (0.131,0.090) 74 Ref.11 1-6 2-2 4.15 6.49 (0.138,0.074) 96 Ref.12 1-8 2-2 4.19 6.51 (0.137,0.079) 106 Ref.13 1-11 2-2 4.20 6.50 (0.140,0.074) 110 Ref.14 1-12 2-2 4.21 6.47 (0.141,0.074) 103 Ref.15 1-13 2-2 4.20 6.53 (0.138,0.080) 102 Ref.16 1-17 2-2 4.19 6.47 (0.137,0.079) 96

[0380] Comparative Examples 17-24 (Ref. 17-24): Fabrication of OLEDs

[0381] OLEDs were manufactured in which the EML contained compound 2-3 as a host and each of compound 1-1 (Ref. 17), compound 1-4 (Ref. 18), compound 1-6 (Ref. 19), compound 1-8 (Ref. 20), compound 1-11 (Ref. 21), compound 1-12 (Ref. 22), compound 1-13 (Ref. 23), and compound 1-17 (Ref. 24) in Formula 3 as a dopant, respectively.

[0382] Comparative Examples 25-32 (Ref. 25-32): OLED Manufacturing

[0383] OLEDs were fabricated in which the EML contained compounds 2-4 as hosts and compounds 1-1 (Ref. 25), 1-4 (Ref. 26), 1-6 (Ref. 27), 1-8 (Ref. 28), 1-11 (Ref. 29), 1-12 (Ref. 30), 1-13 (Ref. 31), and 1-17 (Ref. 32) in Formula 3 as dopants, respectively.

[0384] Experimental Example 2: Measurement of OLED Light Emitting Characteristics

[0385] The light emitting characteristics of each of the OLEDs manufactured in Comparative Examples 17 to 32 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 2 below.

[0386] Table 2: Light-emitting characteristics of OLEDs

[0387]

[0388] Comparative Examples 33-40 (Ref. 33-40): Fabrication of OLEDs

[0389] OLEDs were fabricated in which the EML contained compounds 2-5 as hosts and compounds 1-1 (Ref. 33), 1-4 (Ref. 34), 1-6 (Ref. 35), 1-8 (Ref. 36), 1-11 (Ref. 37), 1-12 (Ref. 38), 1-13 (Ref. 39), and 1-17 (Ref. 40) in Formula 3 as dopants, respectively.

[0390] Comparative Examples 41-48 (Ref. 41-48): Fabrication of OLEDs

[0391] OLEDs were fabricated in which the EML contained compound 2-6 as a host and compound 1-1 (Ref. 41), compound 1-4 (Ref. 42), compound 1-6 (Ref. 43), compound 1-8 (Ref. 44), compound 1-11 (Ref. 45), compound 1-12 (Ref. 46), compound 1-13 (Ref. 47), and compound 1-17 (Ref. 48) in Formula 3 as dopants, respectively.

[0392] Experimental Example 3: Measurement of OLED Light Emitting Characteristics

[0393] The light emitting characteristics of each of the OLEDs manufactured in Comparative Examples 33 to 48 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 3 below.

[0394] Table 3: Light-emitting characteristics of OLEDs

[0395]

[0396] Example 1-8: Fabrication of OLED

[0397] OLEDs were manufactured in which the EML contained compound 2-7 as a host and compound 1-1 (Ex. 1), compound 1-4 (Ex. 2), compound 1-6 (Ex. 3), compound 1-8 (Ex. 4), compound 1-11 (Ex. 5), compound 1-12 (Ex. 6), compound 1-13 (Ex. 7), and compound 1-17 (Ex. 8) in Formula 3 as dopants, respectively.

[0398] Example 9-16 (Ref. 9-16): Fabrication of OLED

[0399] OLEDs were manufactured in which the EML contained compound 2-8 as a host and compound 1-1 (Ex.9), compound 1-4 (Ex.10), compound 1-6 (Ex.11), compound 1-8 (Ex.12), compound 1-11 (Ex.13), compound 1-12 (Ex.14), compound 1-13 (Ex.15) and compound 1-17 (Ex.16) in Formula 3 as dopants, respectively.

[0400] Experimental Example 4: Measurement of OLED Light Emitting Characteristics

[0401] The light emitting characteristics of each of the OLEDs manufactured in Examples 1 to 16 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 4 below.

[0402] Table 4: Light-emitting characteristics of OLEDs

[0403]

[0404] Examples 17-24: Fabrication of OLEDs

[0405] An OLED was manufactured in which the EML contained compound 2-9 as a host and compound 1-1 (Ex. 17), compound 1-4 (Ex. 18), compound 1-6 (Ex. 19), compound 1-8 (Ex. 20), compound 1-11 (Ex. 21), compound 1-12 (Ex. 22), compound 1-13 (Ex. 23) and compound 1-17 (Ex. 24) in Formula 3 as dopants, respectively.

[0406] Examples 25-32 (Ref. 25-32): Fabrication of OLEDs

[0407] OLEDs were manufactured in which the EML contained compound 2-10 as a host and compound 1-1 (Ex.25), compound 1-4 (Ex.26), compound 1-6 (Ex.27), compound 1-8 (Ex.28), compound 1-11 (Ex.29), compound 1-12 (Ex.30), compound 1-13 (Ex.31) and compound 1-17 (Ex.32) in Formula 3 as dopants, respectively.

[0408] Experimental Example 5: Measurement of OLED Luminescence Characteristics

[0409] The light emitting characteristics of each of the OLEDs manufactured in Examples 17 to 32 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 5 below.

[0410] Table 5: Light-emitting characteristics of OLEDs

[0411]

[0412] Examples 33-40: Fabrication of OLEDs

[0413] An OLED was manufactured in which the EML contained compound 2-11 as a host and compound 1-1 (Ex.33), compound 1-4 (Ex.34), compound 1-6 (Ex.35), compound 1-8 (Ex.36), compound 1-11 (Ex.37), compound 1-12 (Ex.38), compound 1-13 (Ex.39) and compound 1-17 (Ex.40) in Formula 3 as dopants, respectively.

[0414] Examples 41-48 (Ref. 41-48): Fabrication of OLEDs

[0415] OLEDs were manufactured in which the EML contained compound 2-12 as a host and compound 1-1 (Ex.41), compound 1-4 (Ex.42), compound 1-6 (Ex.43), compound 1-8 (Ex.44), compound 1-11 (Ex.45), compound 1-12 (Ex.46), compound 1-13 (Ex.47) and compound 1-17 (Ex.48) in Formula 3 as dopants, respectively.

[0416] Experimental Example 6: Measurement of OLED Light Emitting Characteristics

[0417] The light emitting characteristics of each of the OLEDs manufactured in Examples 33 to 48 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 6 below.

[0418] Table 6: Light-emitting characteristics of OLEDs

[0419]

[0420] Summarizing the results in Tables 1 to 6, the OLEDs manufactured in Ex. 1 to Ex. 48 in which the EML includes deuterated anthracene compounds (Compounds 2-7 to 2-12) as the main body have improved luminous efficiency and luminous lifetime compared to the OLEDs manufactured in Ref. 1 to Ref. 48 in which the EML includes non-deuterated anthracene compounds (Compounds 2-1 to 2-6) as the main body.

[0421] Furthermore, the OLEDs manufactured in Ex. 1-8, in which the EML contained compound 2-7 as a host, and the OLEDs manufactured in Ex. 9-16, in which the EML contained compound 2-9 as a host, showed improved luminous efficiency and luminous lifetime compared to the OLEDs manufactured in Ex. 17-48. In other words, when a deuterated anthracene compound in which a naphthyl moiety (1-naphthyl) is directly attached to one side of the anthracene moiety and another naphthyl moiety (2-naphthyl) is attached to the other side of the anthracene moiety directly or via a bridging group (linker) as a host in the EML, the luminous efficiency and luminous lifetime of the OLEDs were further improved.

[0422] In addition, compared to the OLED fabricated in Ex. 1-8, in which the EML contained Compound 2-7 as a host, the OLED fabricated in Ex. 9-16, in which the EML contained Compound 2-8 as a host, exhibited a sufficient luminescence lifetime. In contrast, the OLED in which the EML contained Compound 2-7 as a host had a reduced driving voltage. In other words, the OLED in which the EML contained an anthracene compound in which a naphthyl moiety (1-naphthyl) was directly attached to one side of the anthracene moiety and the other naphthyl moiety (2-naphthyl) was attached directly or via a bridging group and was deuterated, had a reduced driving voltage and improved luminous efficiency and luminescence lifetime.

[0423] In addition, compared with OLEDs whose EMLs include boron-based compounds with symmetrical chemical structures (Compounds 1-1 and 1-4) as dopants, OLEDs whose EMLs include boron-based compounds with asymmetric chemical structures (Compounds 1-6 and 1-8) as dopants have improved their luminous efficiency and luminous lifetime.

[0424] Furthermore, OLEDs with an EML containing deuterated, asymmetric boron compounds (compounds 1-11, 1-12, 1-13, and 1-17) as dopants further improved their luminous efficiency and lifetime. In particular, OLEDs with improved luminescence performance can be achieved when the HIL and HTL include the compound of Formula 11 and the EBL includes the amine compound of Formula 5.

[0425] Manufacturing of Organic Light-Emitting Diodes (OLEDs)2

[0426] A glass substrate (40 mm × 40 mm × 0.5 mm) coated with a thin film of ITO was washed with a solvent such as isopropyl alcohol, acetone, and distilled water, ultrasonically cleaned for 5 minutes, and dried in an oven at 100°C. After cleaning the substrate, the substrate was treated with O2 plasma under vacuum for 2 minutes and then transferred to a vacuum chamber for deposition of the light-emitting layer. Subsequently, at about 5 to 7 × 10 - 7 Torr, by evaporation from a heated boat, The light-emitting layer and cathode are deposited in the following order at a deposition rate of:

[0427] HIL (Formula 11 (97 wt%) and Formula 12 (3 wt%), ); HTL (Formula 11, ); EBL EML (host (H, 98 wt%) and dopant (D, 2 wt%), ); HBL EIL (Formula 13 (98 wt%), Li (2 wt%), ); and cathode (Al, ).

[0428] The OLED is then encapsulated with UV-curable epoxy resin and a moisture-proof agent.

[0429] Comparative Example 49 (Ref. 49): Production of OLED

[0430] An OLED was manufactured in which the EBL included the following Ref. EBL, the EML included Compound 1-1 (dopant) and Compound 2-1 (host) in Formula 2, and the HBL included the following Ref. HBL.

[0431] Examples 49-56: Fabrication of OLEDs

[0432] OLEDs were manufactured in which the EML contained compound 1-1 (dopant) in Formula 2 and compounds 2-7 (host) in Formula 4, the EBL contained the following Ref. EBL (Ex. 49-51), H4 (Ex. 52-54) in Formula 6, or H3 (Ex. 55-57) in Formula 6, respectively, and the HBL contained the following Ref. HBL (Ex. 49, 52, and 55), E1 (Ex. 50, 53, and 56) in Formula 8, or F1 (Ex. 51, 54, and 57) in Formula 10, respectively.

[0433] [Reference compound]

[0434]

[0435] Experimental Example 7: Measurement of OLED Light Emitting Characteristics

[0436] The light emitting characteristics of each of the OLEDs manufactured in Examples 49 to 57 and Comparative Example 49 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 7 below.

[0437] Table 7: Light-emitting characteristics of OLEDs

[0438] sample EBL D H HBL V EQE (%) CIE(x) CIE(y) <![CDATA[T 95 (hr)]]> Ref.49 Ref. 1-1 2-1 Ref. 4.00 3.00 0.140 0.063 22 Ex.49 Ref. 1-1 2-7 Ref. 4.02 2.97 0.140 0.062 30 Ex.50 Ref. 1-1 2-7 E1 4.01 2.99 0.140 0.061 38 Ex.51 Ref. 1-1 2-7 F1 3.96 3.04 0.140 0.060 46 Ex.52 H4 1-1 2-7 Ref. 4.01 5.85 0.139 0.060 87 Ex.53 H4 1-1 2-7 E1 3.98 5.99 0.140 0.060 115 Ex.54 H4 1-1 2-7 F1 3.98 6.17 0.140 0.060 133 Ex.55 H3 1-1 2-7 Ref. 4.01 6.20 0.139 0.62 85 Ex.56 H3 1-1 2-7 E1 4.00 6.31 0.141 0.059 114 Ex.57 H3 1-1 2-7 F1 3.96 6.48 0.141 0.060 124

[0439] Comparative Example 50 (Ref. 50): Production of OLED

[0440] An OLED was manufactured in which the EBL included Ref.EBL, the EML included Compound 1-1 (dopant) and Compound 2-3 (host) in Formula 2, and the HBL included Ref.HBL.

[0441] Examples 58-66: Fabrication of OLEDs

[0442] OLEDs were manufactured in which the EML contained compound 1-1 (dopant) in Formula 2 and compound 2-9 (host) in Formula 4, the EBL contained Ref.EBL (Ex.58-60), H4 (Ex.61-63) in Formula 6, or H3 (Ex.64-66) in Formula 6, respectively, and the HBL contained Ref.HBL (Ex.58, 61, and 64), E1 (Ex.59, 62, and 65) in Formula 8, or F1 (Ex.60, 63, and 66) in Formula 10, respectively.

[0443] Experimental Example 8: Measurement of OLED Luminescence Characteristics

[0444] The light emitting characteristics of each of the OLEDs manufactured in Examples 58 to 66 and Comparative Example 50 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 8 below.

[0445] Table 8: Light-emitting characteristics of OLEDs

[0446] sample EBL D H HBL V EQE (%) CIE(x) CIE(y) <![CDATA[T 95 (hr)]]> Ref.50 Ref. 1-1 2-3 Ref. 3.86 2.92 0.139 0.064 21 Ex.58 Ref. 1-1 2-9 Ref. 3.87 2.93 0.140 0.063 28 Ex.59 Ref. 1-1 2-9 E1 3.83 2.98 0.139 0.062 36 Ex.60 Ref. 1-1 2-9 F1 3.90 3.08 0.141 0.062 39 Ex.61 H4 1-1 2-9 Ref. 3.86 5.81 0.140 0.063 83 Ex.62 H4 1-1 2-9 E1 3.81 5.93 0.139 0.062 102 Ex.63 H4 1-1 2-9 F1 3.90 6.11 0.140 0.063 116 Ex.64 H3 1-1 2-9 Ref. 3.89 6.15 0.139 0.064 79 Ex.65 H3 1-1 2-9 E1 3.82 6.22 0.139 0.062 97 Ex.66 H3 1-1 2-9 F1 3.89 6.41 0.140 0.061 115

[0447] Comparative Example 51 (Ref. 51): Production of OLED

[0448] An OLED was manufactured in which the EBL included Ref.EBL, the EML included Compound 1-4 (dopant) and Compound 2-1 (host) in Formula 2, and the HBL included Ref.HBL.

[0449] Examples 67-75: Fabrication of OLEDs

[0450] OLEDs were manufactured in which the EML contained compounds 1 to 4 (dopants) in Formula 2 and compounds 2 to 7 (hosts) in Formula 4, the EBL contained Ref. EBL (Ex. 67 to 69), H4 (Ex. 70 to 72) in Formula 6, or H3 (Ex. 73 to 75) in Formula 6, respectively, and the HBL contained Ref. HBL (Ex. 67, 70, and 73), E1 (Ex. 68, 71, and 74) in Formula 8, or F1 (Ex. 69, 72, and 75) in Formula 10, respectively.

[0451] Experimental Example 9: Measurement of OLED Luminescence Characteristics

[0452] The light emitting characteristics of each of the OLEDs manufactured in Examples 67 to 75 and Comparative Example 51 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 9 below.

[0453] Table 9: Light-emitting characteristics of OLEDs

[0454]

[0455]

[0456] Comparative Example 52 (Ref. 52): Production of OLED

[0457] An OLED was manufactured in which the EBL included Ref.EBL, the EML included Compounds 1-4 (dopant) and Compounds 2-3 (host) in Formula 2, and the HBL included Ref.HBL.

[0458] Examples 76-84: Fabrication of OLEDs

[0459] OLEDs were manufactured in which the EML contained compounds 1 to 4 (dopants) in Formula 2 and compounds 2 to 9 (hosts) in Formula 4, the EBL contained Ref. EBL (Ex. 76 to 78), H4 (Ex. 79 to 81) in Formula 6, or H3 (Ex. 82 to 84) in Formula 6, respectively, and the HBL contained Ref. HBL (Ex. 76, 79, and 82), E1 (Ex. 77, 80, and 83) in Formula 8, or F1 (Ex. 78, 81, and 84) in Formula 10, respectively.

[0460] Experimental Example 10: Measurement of OLED Luminescence Characteristics

[0461] The light emitting characteristics of each of the OLEDs manufactured in Examples 76 to 84 and Comparative Example 52 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 10 below.

[0462] Table 10: Light-emitting characteristics of OLEDs

[0463] sample EBL D H HBL V EQE (%) CIE(x) CIE(y) <![CDATA[T 95 (hr)]]> Ref.52 Ref. 1-4 2-3 Ref. 3.82 2.89 0.131 0.092 20 Ex.76 Ref. 1-4 2-9 Ref. 3.87 2.89 0.131 0.092 29 Ex.77 Ref. 1-4 2-9 E1 3.80 2.97 0.131 0.091 36 Ex.78 Ref. 1-4 2-9 F1 3.87 3.08 0.132 0.091 44 Ex.79 H4 1-4 2-9 Ref. 3.85 5.77 0.130 0.092 84 Ex.80 H4 1-4 2-9 E1 3.80 5.91 0.131 0.092 109 Ex.81 H4 1-4 2-9 F1 3.82 6.09 0.131 0.091 133 Ex.82 H3 1-4 2-9 Ref. 3.85 6.09 0.131 0.091 83 Ex.83 H3 1-4 2-9 E1 3.77 6.23 0.131 0.092 110 Ex.84 H3 1-4 2-9 F1 3.85 6.39 0.130 0.092 131

[0464] Comparative Example 53 (Ref. 53): Production of OLED

[0465] An OLED was manufactured in which the EBL included Ref.EBL, the EML included Compound 1-6 (dopant) and Compound 2-1 (host) in Formula 2, and the HBL included Ref.HBL.

[0466] Examples 85-93: Fabrication of OLEDs

[0467] OLEDs were manufactured in which the EML contained compounds 1 to 6 (dopants) in Formula 2 and compounds 2 to 7 (hosts) in Formula 4, the EBL contained Ref. EBL (Ex. 85 to 87), H4 (Ex. 88 to 90) in Formula 6, or H3 (Ex. 91 to 93) in Formula 6, respectively, and the HBL contained Ref. HBL (Ex. 85, 88, and 91), E1 (Ex. 86, 89, and 92) in Formula 8, or F1 (Ex. 87, 90, and 93) in Formula 10, respectively.

[0468] Experimental Example 11: Measurement of OLED Luminescence Characteristics

[0469] The light emitting characteristics of each of the OLEDs manufactured in Examples 85 to 93 and Comparative Example 53 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 11 below.

[0470] Table 11: Light-emitting characteristics of OLEDs

[0471] sample EBL D H HBL V EQE (%) CIE(x) CIE(y) <![CDATA[T 95 (hr)]]> Ref.53 Ref. 1-6 2-1 Ref. 3.93 3.11 0.140 0.076 26 Ex.85 Ref. 1-6 2-7 Ref. 3.95 3.09 0.140 0.075 45 Ex.86 Ref. 1-6 2-7 E1 3.95 3.14 0.141 0.074 54 Ex.87 Ref. 1-6 2-7 F1 3.91 3.19 0.140 0.075 61 Ex.88 H4 1-6 2-7 Ref. 3.96 6.13 0.140 0.076 122 Ex.89 H4 1-6 2-7 E1 3.91 6.27 0.140 0.074 161 Ex.90 H4 1-6 2-7 F1 3.91 6.38 0.140 0.074 190 Ex.91 H3 1-6 2-7 Ref. 3.93 6.45 0.139 0.077 110 Ex.92 H3 1-6 2-7 E1 3.92 6.58 0.140 0.074 150 Ex.93 H3 1-6 2-7 F1 3.92 6.70 0.140 0.074 177

[0472] Comparative Example 54 (Ref. 54): Production of OLED

[0473] An OLED was fabricated in which the EBL included Ref.EBL, the EML included Compounds 1-6 (dopant) and Compounds 2-3 (host) in Formula 2, and the HBL included Ref.HBL.

[0474] Example 94-102: Fabrication of OLED

[0475] OLEDs were manufactured in which the EML contained compounds 1 to 6 (dopants) in Formula 2 and compounds 2 to 9 (hosts) in Formula 4, the EBL contained Ref. EBL (Ex. 94 to 96), H4 (Ex. 97 to 99) in Formula 6, or H3 (Ex. 100 to 102) in Formula 6, respectively, and the HBL contained Ref. HBL (Ex. 94, 97, and 100), E1 (Ex. 95, 98, and 101) in Formula 8, or F1 (Ex. 96, 99, and 102) in Formula 10, respectively.

[0476] Experimental Example 12: Measurement of OLED Luminescence Characteristics

[0477] The light emitting characteristics of each of the OLEDs manufactured in Examples 94 to 102 and Comparative Example 54 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 12 below.

[0478] Table 12: Light-emitting characteristics of OLEDs

[0479] sample EBL D H HBL V EQE (%) CIE(x) CIE(y) <![CDATA[T 95 (hr)]]> Ref.54 Ref. 1-6 2-3 Ref. 3.82 3.01 0.139 0.076 28 Ex.94 Ref. 1-6 2-9 Ref. 3.84 3.03 0.138 0.081 38 Ex.95 Ref. 1-6 2-9 E1 3.81 3.09 0.137 0.080 49 Ex.96 Ref. 1-6 2-9 F1 3.82 3.19 0.138 0.081 58 Ex.97 H4 1-6 2-9 Ref. 3.85 6.05 0.138 0.081 112 Ex.98 H4 1-6 2-9 E1 3.79 6.13 0.137 0.081 145 Ex.99 H4 1-6 2-9 F1 3.80 6.31 0.137 0.082 174 Ex.100 H3 1-6 2-9 Ref. 3.83 6.36 0.138 0.081 106 Ex.101 H3 1-6 2-9 E1 3.79 6.41 0.138 0.079 136 Ex.102 H3 1-6 2-9 F1 3.80 6.60 0.137 0.082 169

[0480] Comparative Example 55 (Ref. 55): Production of OLED

[0481] An OLED was manufactured in which the EBL included Ref.EBL, the EML included Compound 1-8 (dopant) and Compound 2-1 (host) in Formula 2, and the HBL included Ref.HBL.

[0482] Example 103-111: Fabrication of OLED

[0483] OLEDs were manufactured in which the EML contained compounds 1 to 8 (dopants) in Formula 2 and compounds 2 to 7 (hosts) in Formula 4, the EBL contained Ref. EBL (Ex. 103 to 105), H4 (Ex. 106 to 108) in Formula 6, or H3 (Ex. 109 to 111) in Formula 6, respectively, and the HBL contained Ref. HBL (Ex. 103, 106, and 109), E1 (Ex. 104, 107, and 110) in Formula 8, or F1 (Ex. 105, 108, and 111) in Formula 10, respectively.

[0484] Experimental Example 13: Measurement of OLED Luminescence Characteristics

[0485] The light emitting characteristics of each of the OLEDs manufactured in Examples 103-111 and Comparative Example 55 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 13 below.

[0486] Table 13: Light-emitting characteristics of OLEDs

[0487] sample EBL D H HBL V EQE (%) CIE(x) CIE(y) <![CDATA[T 95 (hr)]]> Ref.55 Ref. 1-8 2-1 Ref. 3.92 3.12 0.136 0.081 28 Ex.103 Ref. 1-8 2-7 Ref. 3.93 3.08 0.139 0.082 42 Ex.104 Ref. 1-8 2-7 E1 3.87 3.17 0.137 0.081 50 Ex.105 Ref. 1-8 2-7 F1 3.91 3.22 0.137 0.082 59 Ex.106 H4 1-8 2-7 Ref. 3.92 6.17 0.138 0.081 119 Ex.107 H4 1-8 2-7 E1 3.88 6.29 0.137 0.080 149 Ex.108 H4 1-8 2-7 F1 3.89 6.44 0.137 0.081 175 Ex.109 H3 1-8 2-7 Ref. 3.90 6.48 0.138 0.081 118 Ex.110 H3 1-8 2-7 E1 3.88 6.67 0.138 0.081 142 Ex.111 H3 1-8 2-7 F1 3.89 6.72 0.136 0.082 167

[0488] Comparative Example 56 (Ref. 56): Production of OLED

[0489] An OLED was manufactured in which the EBL included Ref.EBL, the EML included Compounds 1-8 (dopant) and Compounds 2-3 (host) in Formula 2, and the HBL included Ref.HBL.

[0490] Examples 112-120: Fabrication of OLEDs

[0491] OLEDs were manufactured in which the EML contained compounds 1 to 8 (dopants) in Formula 2 and compounds 2 to 9 (hosts) in Formula 4, the EBL contained Ref. EBL (Ex. 112 to 114), H4 (Ex. 115 to 117) in Formula 6, or H3 (Ex. 118 to 120) in Formula 6, respectively, and the HBL contained Ref. HBL (Ex. 112, 115, and 118), E1 (Ex. 113, 116, and 119) in Formula 8, or F1 (Ex. 114, 117, and 120) in Formula 10, respectively.

[0492] Experimental Example 14: Measurement of OLED Light Emitting Characteristics

[0493] The light emitting characteristics of each of the OLEDs manufactured in Examples 112 to 120 and Comparative Example 56 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 14 below.

[0494] Table 14: Light-emitting characteristics of OLEDs

[0495] sample EBL D H HBL V EQE (%) CIE(x) CIE(y) <![CDATA[T 95 (hr)]]> Ref.56 Ref. 1-8 2-3 Ref. 3.80 3.05 0.137 0.081 27 Ex.112 Ref. 1-8 2-9 Ref. 3.81 3.07 0.138 0.083 36 Ex.113 Ref. 1-8 2-9 E1 3.76 3.06 0.137 0.083 42 Ex.114 Ref. 1-8 2-9 F1 3.80 3.18 0.137 0.083 52 Ex.115 H4 1-8 2-9 Ref. 3.82 6.05 0.137 0.083 107 Ex.116 H4 1-8 2-9 E1 3.78 6.12 0.136 0.084 132 Ex.117 H4 1-8 2-9 F1 3.79 6.30 0.136 0.084 156 Ex.118 H3 1-8 2-9 Ref. 3.84 6.38 0.137 0.083 102 Ex.119 H3 1-8 2-9 E1 3.76 6.42 0.136 0.084 129 Ex.120 H3 1-8 2-9 F1 3.81 6.62 0.136 0.083 144

[0496] Summarizing the results in Tables 7 to 14, the OLEDs manufactured in Ex.49 to Ex.120, in which the EML includes a deuterated anthracene compound (Compound 2-7 or Compound 2-9) as the main body, have improved luminous efficiency and luminous lifetime compared to the OLEDs manufactured in Ref.49 to Ref.56, in which the EML includes a non-deuterated anthracene compound (Compound 2-1 or Compound 2-3) as the main body.

[0497] Furthermore, the OLEDs fabricated in Ex. 49-57, 67-75, 85-93, and 103-111, in which the EML contained compound 2-7 as a host, had improved luminous efficiency and luminous lifetime compared to the OLEDs fabricated in Ex. 58-66, 76-84, 94-102, and 112-120, in which the EML contained compound 2-9 as a host. In other words, when a deuterated anthracene compound in which a naphthyl moiety (1-naphthyl) is directly attached to one side of the anthracene moiety and another naphthyl moiety (2-naphthyl) is attached to the other side of the anthracene moiety directly or via a bridging group (linker) and is used as a host in the EML, the luminous efficiency and luminous lifetime of the OLED are further improved.

[0498] In addition, when the boron compound with an asymmetric chemical structure (Compound 1-6 or Compound 1-8) is used as a dopant in the EML, the luminous efficiency and luminous lifetime of the OLED are further improved. In particular, when Compound 1-6 (in Formula 1B, R 91 is an alkyl group (tert-butyl), R 81 and R 82When aryl groups (phenyl groups), each of which is substituted with an alkyl group (tert-butyl group), are used as dopants in the EML, the luminous efficiency and luminous lifetime of the OLED are significantly improved.

[0499] Furthermore, when the HBL includes the azine compound of Formula 8 or the benzimidazole compound of Formula 10, the OLED exhibits very excellent luminous efficiency and luminous lifetime. In addition, when the HBL includes the amine compound of Formula 6, the luminous efficiency and luminous lifetime of the OLED can be maximized.

[0500] In addition, when the EML includes a deuterated anthracene compound (Compound 2-7 or Compound 2-9) and a boron compound of Formula 1B, the EBL includes an amine compound of Formula 5, and the HBL includes an azine compound of Formula 7 or a benzimidazole compound of Formula 9, the luminous efficiency and luminous lifetime of the OLED are significantly improved.

[0501] It is obvious to those skilled in the art that various modifications and variations can be made to the present disclosure without departing from the scope of the present disclosure. Therefore, the present disclosure is intended to cover the modifications and variations of the present disclosure as long as they fall within the scope of the appended claims.

Claims

1. An organic light-emitting device, comprising: substrate; and an organic light emitting diode on the substrate, the organic light emitting diode comprising a first electrode, a second electrode facing the first electrode, and a light emitting layer disposed between the first electrode and the second electrode, The light-emitting layer includes: a first light-emitting material layer containing a first dopant and a first host, and a first electron blocking layer arranged between the first electrode and the first light-emitting material layer. The first dopant includes a boron compound having the structure of the following formula 1B: The first host includes an anthracene compound having a structure of the following formula 3, and The first electron blocking layer includes an amine compound having a structure of the following formula 5: [Formula 1B] wherein X is NR1, CR2R3, O, S, Se or SiR4R5, and R1 to R5 are each independently selected from hydrogen, C1-C 10 Alkyl, C6-C 30 Aryl, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups; R 61 to R 64 Each independently selected from hydrogen, C1-C 10 Alkyl, C6-C 30 Aryl, C6-C 30 Arylamino, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups, or R 61 to R 64 The two adjacent ones form a fused ring, where R 61 to R 64 The aryl, arylamino, heteroaryl and alicyclic groups are each independently free of substituents or substituted with at least one C1-C 10 Alkyl; R 71 to R 74 Each independently selected from hydrogen, C1-C 10 Alkyl and C3-C 30 A group consisting of alicyclic groups; R 81 Choose from C6-C 30 Aryl, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups, or R 81 and R 61 Form a fused ring, where R 81 The aryl, heteroaryl and alicyclic groups are each independently free of substituents or substituted with at least one C1-C 10 Alkyl; R 82 Choose from C6-C 30 Aryl, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups, wherein R 82 The aryl, heteroaryl and alicyclic groups are each independently free of substituents or substituted with at least one C1-C 10 Alkyl; R 91 Selected from hydrogen, C1-C 10 Alkyl, C3-C 15 Cycloalkyl, C6-C 30 Aryl, C6-C 30 Arylamino, C5-C 30 Heteroaryl and C3-C 30 A group consisting of alicyclic groups, wherein R 91 The cycloalkyl, aryl, arylamino, heteroaryl and alicyclic groups are each independently free of substituents or substituted with at least one C1-C 10 Alkyl; when R 81 、R 82 and R 91 Each is substituted with at least one C1-C 10 Alkyl C6-C 30 In the case of an aryl group, the substituted alkyl groups are linked to each other to form a fused ring; [Formula 3] wherein Ar1 and Ar2 are each independently C6-C 30 Aryl or C5-C 30 Heteroaryl; L is a single bond, C6-C 20 Arylene or C5-C 20 heteroarylene; a is an integer from 0 to 8; b, c and d are each independently an integer from 0 to 30, wherein at least one of a, b, c and d is a positive integer; [Formula 5] Among them, L3 is C6-C 30 Arylene; o is 0 or 1; R 121 and R 122 Each independently is C6-C 30 Aryl or C5-C 30 Heteroaryl, wherein the C6-C 30 Aryl or the C5-C 30 The heteroaryl groups are each independently unsubstituted or substituted with C1-C 10 Alkyl and C6-C 30 At least one of the aryl groups.

2. The organic light-emitting device according to claim 1, wherein: X in Formula 1B is O or S, wherein R in Formula 1B 61 to R 64 Each independently selected from hydrogen, C1-C 10 Alkyl and C6-C 30 A group consisting of an arylamino group, or R 61 to R 64 The two adjacent ones form a fused ring, where R 71 to R 74 Each independently selected from hydrogen and C1-C 10 A group consisting of alkyl groups, wherein R 81 Choose from C6-C 30 Aryl and C5-C 30 A group consisting of heteroaryl, or R 81 and R 61 Form a fused ring, where R 81 The aryl and heteroaryl groups are each independently unsubstituted or substituted with C1-C 10 Alkyl, where R 82 Choose from C6-C 30 Aryl and C5-C 30 The group consisting of heteroaryl groups, wherein R 82 The aryl and heteroaryl groups are each independently unsubstituted or substituted with C1-C 10 alkyl, and wherein R 91 C1-C 10 alkyl.

3. The organic light-emitting device according to claim 1, wherein: The first dopant is selected from the following boron compounds:

4. The organic light-emitting device according to claim 1, wherein: The first host is selected from the following anthracene compounds:

5. The organic light-emitting device according to claim 1, wherein: The amine compound is selected from the following amine compounds: The organic light-emitting device according to claim 1 , wherein: The light emitting layer further includes a first hole blocking layer disposed between the first light emitting material layer and the second electrode.

7. The organic light-emitting device according to claim 6, wherein: The first hole blocking layer includes at least one of an azine compound having a structure of the following formula 7 and a benzimidazole compound having a structure of the following formula 9: [Formula 7] wherein Y1 to Y5 are each independently CR 131 or N, one to three of Y1 to Y5 are N, and R 131 It is C6-C 30 Aryl; L is C6-C 30 Arylene; R 132 It is C6-C 30 Aryl or C5-C 30 Heteroaryl, wherein the C6-C 30 Aryl groups independently have no substituent or are substituted with another C6-C 30 Aryl or C5-C 30 Heteroaryl, or with C 10 -C 30 Fused aryl ring or C 10 -C 30 The fused heteroaryl ring forms a spirocyclic structure wherein the other C6-C 30 The aryl groups independently have no substituents or are further substituted with other C6-C 30 Aryl or C5-C 30 Heteroaryl, or with C 10 -C 30 The fused aromatic rings form a spiro ring structure; R 133 is hydrogen, or two adjacent R 133 forming a fused aromatic ring; r is 0 or 1; s is 1 or 2; and t is an integer from 0 to 4; [Formula 9] Where Ar is C 10 -C 30 Arylene; R 141 It is C6-C 30 Aryl or C5-C 30 Heteroaryl, the C6-C 30 Aryl and the C5-C 30 The heteroaryl groups are each independently unsubstituted or substituted with C1-C 10 alkyl; and R 142 and R 143 are independently hydrogen, C1-C 10 Alkyl or C6-C 30 Aryl.

8. The organic light-emitting device according to claim 7, wherein: The azine compound is selected from the following azine compounds:

9. The organic light-emitting device according to claim 7, wherein: The benzimidazole compound is selected from the following benzimidazole compounds:

10. The organic light-emitting device according to claim 1, wherein: The light-emitting layer further includes a second light-emitting material layer disposed between the first light-emitting material layer and the second electrode, and a first charge generation layer disposed between the first light-emitting material layer and the second light-emitting material layer.

11. The organic light-emitting device according to claim 10, wherein: The second light emitting material layer includes a second dopant and a second host, wherein the second dopant includes a boron-based compound having a structure of Formula 1B, and wherein the second host includes an anthracene-based compound having a structure of Formula 3.

12. The organic light-emitting device according to claim 10, wherein: The light emitting layer further includes a second electron blocking layer disposed between the first charge generation layer and the second light emitting material layer, wherein the second electron blocking layer includes an amine compound having a structure of Formula 5.

13. The organic light-emitting device according to claim 10, wherein: The light emitting layer further includes at least one of a first hole blocking layer disposed between the first light emitting material layer and the first charge generation layer and a second hole blocking layer disposed between the second light emitting material layer and the second electrode.

14. The organic light-emitting device according to claim 10, wherein: The light-emitting layer further includes a third light-emitting material layer disposed between the second light-emitting material layer and the second electrode, and a second charge generation layer disposed between the second light-emitting material layer and the third light-emitting material layer.

15. The organic light-emitting device according to claim 1, wherein: The substrate defines a red pixel area, a green pixel area, and a blue pixel area, and the organic light-emitting diodes are correspondingly located in the red pixel area, the green pixel area, and the blue pixel area. The organic light-emitting device also includes a color conversion layer, which corresponds to the red pixel area and the green pixel area and is arranged between the substrate and the organic light-emitting diodes or above the organic light-emitting diodes.

16. The organic light-emitting device according to claim 10, wherein: The second luminescent material layer emits yellow-green light or red-green light.

17. The organic light-emitting device according to claim 14, wherein: The second luminescent material layer emits yellow-green light or red-green light.

18. The organic light-emitting device according to claim 16, wherein: The substrate defines a red pixel area, a green pixel area, and a blue pixel area, and the organic light-emitting diodes are correspondingly located in the red pixel area, the green pixel area, and the blue pixel area. The organic light-emitting device also includes a color filter layer, which corresponds to the red pixel area, the green pixel area, and the blue pixel area, and is arranged between the substrate and the organic light-emitting diodes or above the organic light-emitting diodes.

19. The organic light-emitting device according to claim 17, wherein: The substrate defines a red pixel area, a green pixel area, and a blue pixel area, and the organic light-emitting diodes are correspondingly located in the red pixel area, the green pixel area, and the blue pixel area. The organic light-emitting device also includes a color filter layer, which corresponds to the red pixel area, the green pixel area, and the blue pixel area, and is arranged between the substrate and the organic light-emitting diodes or above the organic light-emitting diodes.

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