Organic light emitting device

Abstract

This disclosure relates to an organic light-emitting device. In particular, this disclosure relates to organic light-emitting diodes (OLEDs) and organic light-emitting devices, each comprising: at least one light-emitting material layer containing a boron-based dopant and an anthracene-based host substituted with at least one deuterium, at least one electron-blocking layer containing an amine compound substituted with at least one fused heteroaryl group, and optionally at least one hole-blocking layer containing an azazine or benzimidazole compound. The OLEDs and organic light-emitting devices exhibit improved luminous efficiency and enhanced luminous lifetime.

Description

[0001] This application claims priority to Korean Patent Application No. 10-2020-0184942, filed on December 28, 2020, in the Republic of Korea, the entire contents of which are hereby expressly incorporated by reference in its entirety into the present application. 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 lifespan. BACKGROUND

[0003] Among widely used flat panel display apparatuses, an organic light emitting diode (OLED) is a focus as a display apparatus rapidly replacing a liquid crystal display apparatus (LCD). The OLED can form an organic thin film of less than 1,000 angstroms, and can achieve a unidirectional or bidirectional image through electrode arrangement. In addition, the OLED can be formed even on a flexible transparent substrate such as a plastic substrate, so that a flexible or foldable display apparatus can be easily realized with the OLED. In addition, the OLED can be driven at a lower voltage than the LCD, and the OLED has excellent high color purity.

[0004] Since a fluorescent material uses only singlet exciton energy in a light emitting process, the fluorescent material of the related art shows low luminous efficiency. In contrast, a phosphorescent material can show high luminous efficiency because it uses both triplet exciton energy and singlet exciton energy in a light emitting process. However, a metal complex as a representative phosphorescent material has a short luminous lifespan in commercial applications. In particular, a blue light emitting material does not exhibit satisfactory luminous efficiency and luminous lifespan compared to light emitting materials of other colors. Therefore, it is necessary to develop a new compound or device structure capable of improving luminous efficiency and luminous lifespan of an organic light emitting diode. SUMMARY

[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 lifespan.

[0007] Additional features and aspects will be set forth in the description that follows, and in part will be apparent from the description, or can be learned by practice of the inventive concepts provided herein. The features and aspects of the present inventive concepts can be realized and attained by the structure particularly pointed out in the written description below as well as the appended drawings to represent a full and enabling disclosure of the present inventive concepts.

[0008] ​To achieve these and other aspects of the present inventive concepts embodied and broadly described herein, 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 an emission layer disposed between the first electrode and the second electrode, wherein the emission layer includes a first emission material layer including a first dopant and a first host, and a first electron blocking layer disposed between the first electrode and the first emission material layer, wherein the first dopant includes a boron-based compound having a structure of Formula 1A or Formula 1B below, wherein the first host includes an anthracene-based compound having a structure of Formula 3 below, and wherein the first electron blocking layer includes an amine-based compound having a structure of Formula 5 below.

[0009] [Formula 1A]

[0010]

[0011] wherein R 11 to R 14 and R 21 to R 24 are each independently selected from the group consisting of hydrogen, C1-C 10 alkyl, C6-C 30 aryl, C6-C 30 arylamino, C5-C 30 heteroaryl, and C3-C 30 alicyclic, or adjacent two of R 11 to R 14 and R 21 to R 24 form a fused ring, wherein the aryl, arylamino, heteroaryl, and alicyclic of R 11 to R 14 and R 21 to R 24 each independently have no substituent or are substituted with at least one C1-C 10 alkyl; R 31 and R 41 are each independently selected from the group consisting of hydrogen, C1-C 10 alkyl, C6-C 30 aryl, C6-C 30 arylamino, C5-C 30 heteroaryl, and C3-C 30 alicyclic, wherein the aryl, arylamino, heteroaryl, and alicyclic of R 31 and R 41 each independently have no substituent or are substituted with at least one C1-C 10 alkyl; R 51 is selected from the group consisting of 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 heterocyclyl, wherein the cycloalkyl, aryl, arylamino, heteroaryl, alicyclic and heterocyclyl groups of R 51 each independently are unsubstituted or substituted with at least one C1-C 10 alkyl; when the cycloalkyl, aryl, arylamino, heteroaryl, alicyclic and heterocyclyl groups of R 31 , R 41 and R 51 each are C6-C 10 aryl substituted with at least one C1-C 30 alkyl, the substituted alkyl groups are connected to each other to form a fused ring;

[0012] [Formula 1B]

[0013]

[0014] wherein X is NR1, CR2R3, O, S, Se or SiR4R5, each of R1to R5is independently selected from the group consisting of hydrogen, C1-C 10 alkyl, C6-C 30 aryl, C5-C 30 heteroaryl and C3-C 30 alicyclic; each of R 61 to R 64 is independently selected from the group consisting of hydrogen, C1-C 10 alkyl, C6-C 30 aryl, C6-C 30 aryl, C5-C 30 heteroaryl and C3-C 30 alicyclic, or adjacent two of R 61 to R 64 form a fused ring, wherein each of the aryl, arylamino, heteroaryl and alicyclic groups of R 61 to R 64 is independently unsubstituted or substituted with at least one C1-C 10 alkyl; each of R 71 to R 74 is independently selected from the group consisting of hydrogen, C1-C 10 alkyl and C3-C 30 alicyclic; R 81 is selected from the group consisting of C6-C 30 aryl, C5-C 30 heteroaryl and C3-C 30 alicyclic, or R 81 and R 61Formation of fused rings, where R 81 The aryl, heteroaryl, and alicyclic groups are each independently unsubstituents or have at least one C1-C substituent. 10 Alkyl; R 82 Choose C6-C freely 30 Aryl, C5-C 30 heteroaryl and C3-C 30 The group consisting of alicyclic groups, wherein R 82 The aryl, heteroaryl, and alicyclic groups are each independently unsubstituents or have at least one C1-C substituent. 10 Alkyl; R 91 Choose free 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 The group consisting of alicyclic groups, wherein R 91 The cycloalkyl, aryl, arylamino, heteroaryl, and alicyclic groups are each independently unsubstituent or have at least one C1-C substituent. 10 Alkyl; when R 81 R 82 and R 91 Each has at least one C1-C as a substitute 10 C6-C of alkyl groups 30 In the case of aryl groups, the substituted alkyl groups are linked together to form a fused ring;

[0015] [Formula 3]

[0016]

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

[0018] [Formula 5]

[0019]

[0020] L3 is C6-C 30 Aromatic; R 121 and R 122 Each independently is either hydrogen or R 121 and R 122 Two adjacent C10 -C 20 fused aryl or C 10 -C 20 fused heteroaryl, wherein the C 10 -C 20 fused aryl and the C 10 -C 20 fused heteroaryl are each independently optionally substituted with C1-C 10 alkyl; R 123 is hydrogen or C6-C 30 aryl; R 124 is C5-C 30 heteroaryl; o is 0 or 1 ; p is the number of substituents R 121 and is an integer from 0 to 4; and q is the number of substituents R 122 and is an integer from 0 to 5.

[0021] As an example, R 11 through R 14 , R 21 through R 24 , R 31 and R 41 may each be independently selected from the group consisting of hydrogen, C1-C 10 alkyl, C6-C 30 aryl and C5-C 30 heteroaryl, wherein the aryl and heteroaryl of R 11 through R 14 , R 21 through R 24 , R 31 and R 41 may each be independently unsubstituted or substituted with C1-C 10 alkyl, wherein R 51 of formula 1A can be selected from the group consisting of C1-C 10 alkyl, C6-C 30 arylamino, C5-C 30 heteroaryl and C3-C 30 heterocyclyl, and wherein the heteroaryl, arylamino and heterocyclyl of R 51 may each be independently unsubstituted or substituted with C1-C 10 alkyl.

[0022] Alternatively, X of formula 1B can be O or S, wherein R 61 through R 64 of formula 1B can each be independently selected from the group consisting of hydrogen, C1-C 10 alkyl and C6-C 30 aryl amino, or R 61 through R 64Two adjacent rings can form a fused ring, where R 71 To R 74 Each can be independently selected from hydrogen and C1-C. 10 The group consisting of alkyl groups, wherein R 81 You can choose the C6-C. 30 Aryl and C5-C 30 Groups composed of heteroaryl groups, or R 81 and R 61 Fused rings can be formed, wherein R 81 The aryl and heteroaryl groups can each independently be unsubstituented or substituted with C1-C2 groups. 10 Alkyl, wherein R 82 You can choose the C6-C. 30 Aryl and C5-C 30 The group consisting of heteroaryl groups, in which R 82 The aryl and heteroaryl groups can each independently be unsubstituented or substituted with C1-C2 groups. 10 Alkyl, and wherein R 91 Can be C1-C 10 alkyl.

[0023] The light-emitting layer may also 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 comprise at least one of an azazine compound having the structure of Formula 7 and a benzimidazole compound having the structure of Formula 9:

[0025] [Formula 7]

[0026]

[0027] Among them, 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 Aromatic; R 132 It is C6-C 30 Aryl or C5-C 30 heteroaryl, of which C6-C 30 The aryl group can optionally be replaced by another C6-C. 30 Aryl or C5-C 30 Mixed aromatics, or with C 10 -C 30 Fused aryl rings or C 10 -C 30 The fused heteroaryl rings form a spirocyclic structure, wherein the other C6-C 30 The aryl group may optionally be further substituted with other C6-C groups.30 aryl or C5-C 30 heteroaryl, or with C 10 -C 30 fused aryl rings form a spiro structure; R 133 is hydrogen, or two R 133 form 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] wherein Ar is C 10 -C 30 arylene; R 141 is C6-C 30 aryl or C5-C 30 heteroaryl, C6-C 30 aryl and C5-C 30 heteroaryl are each optionally substituted with C1-C 10 alkyl; and R 142 and R 143 are each independently hydrogen, C1-C 10 alkyl or C6-C 30 aryl.

[0031] As an alternative, the light-emitting layer can 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 can include a second dopant and a second host, wherein the second dopant can include a boron-based compound having a structure of Formula 1A or Formula 1B, and the second host can include an anthracene-based compound having a structure of Formula 3.

[0033] Further, the light-emitting layer can 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 can include an amine-based compound having a structure of Formula 5.

[0034] The light-emitting layer can 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 can 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 can define red, green, and blue pixel regions, and the organic light emitting diodes can be correspondingly located in the red, green, and blue pixel regions, and the organic light emitting device can further include color conversion layers corresponding to the red and green pixel regions 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 can define red, green, and blue pixel regions, and the organic light emitting diodes can be correspondingly arranged to the red, green, and blue pixel regions, and the organic light emitting device can further include color filter layers corresponding to the red, green, and blue pixel regions arranged between the substrate and the organic light emitting diodes or arranged above the organic light emitting diodes.

[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 claimed. BRIEF DESCRIPTION OF DRAWINGS

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

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

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

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

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

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

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

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

[0048] FIG. 8 is a cross-sectional view illustrating an organic light emitting display device according to yet 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 of the present disclosure can improve its luminous efficiency and its luminous life by applying a specific organic compound to a light emitting material layer, an electron blocking layer, and / or a hole blocking layer. The organic light emitting diode can be applied to an organic light emitting device, such as an organic light emitting display device or an organic light emitting illumination device.

[0051] FIG. 1 is a circuit schematic diagram illustrating an organic light emitting display device of the present disclosure. As shown in FIG. 1 a gate line GL, a data line DL, and a power line PL are formed in the organic light emitting display device, each of which crosses each other to define a pixel region 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 can 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, and 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, a data signal applied to the data line DL is applied to a gate of the driving thin film transistor Td and one electrode of the storage capacitor Cst through the switching thin film transistor Ts.

[0053] The driving thin film transistor Td is turned on by the data signal applied to the gate, so that a current proportional to the data signal is supplied from the power line PL to the organic light emitting diode D through the driving thin film transistor Td. Then, the organic light emitting diode D emits light having a luminance proportional to the current flowing through the driving thin film transistor Td. In this case, the storage capacitor Cst is charged with a voltage proportional to the data signal, so as to maintain the voltage of the gate of the driving thin film transistor Td constant during one frame. Accordingly, the organic light emitting display device can display a desired image.

[0054] FIG. 2 is a cross-sectional view illustrating an organic light emitting display device according to still another exemplary aspect of the present disclosure. As shown in FIG. 2As illustrated, the organic light emitting display device 100 includes a substrate 102, a thin film transistor Tr over 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 the organic light emitting diode D is located in each pixel region. In other words, the organic light emitting diodes D each emitting red, green, or blue (B) light are correspondingly located in the red pixel region, the green pixel region, and the blue pixel region.

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

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

[0057] A semiconductor layer 110 is disposed on the buffer layer 106. In one exemplary aspect, the semiconductor layer 110 can include, but is not limited to, an oxide semiconductor material. In this case, a light blocking pattern can be disposed under the semiconductor layer 110, which can prevent light from being incident to the semiconductor layer 110, thereby preventing the semiconductor layer 110 from being deteriorated by light. Alternatively, the semiconductor layer 110 can include polysilicon. In this case, opposite edges of the semiconductor layer 110 can be doped with impurities.

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

[0059] A gate 130 made of a conductive material such as metal is disposed on the gate insulating layer 120, corresponding to a center of the semiconductor layer 110. Although the gate insulating layer 120 is disposed on the entire area of the substrate 102 in FIG. 2 , the gate insulating layer 120 can be patterned the same as 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 can include an inorganic insulating material such as silicon oxide (SiO x ) or silicon nitride (SiN x) or an organic insulating material 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, which expose 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, spaced apart from the gate 130. The first semiconductor layer contact hole 142 and the second semiconductor layer contact hole 144 are formed in the gate insulating layer 120 in FIG. 2

[0062] The source 152 and the drain 154 are arranged on the interlayer insulating layer 140, and are made of a conductive material such as metal. The source 152 and the drain 154 are spaced apart from each other with respect 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 130, the source 152 and the drain 154 constitute a thin film transistor Tr, which functions as a drive element. FIG. 2 The thin film transistor Tr in

[0064] Although not shown in FIG. 2 , gate lines and data lines, which cross each other to define pixel regions, and switching elements connected to the gate lines and the data lines can be further formed in the pixel regions. The switching elements are connected to the thin film transistor Tr, which functions as a drive element. In addition, a power supply line is spaced apart from the gate lines or the data lines in parallel, and the thin film transistor Tr can further include a storage capacitor configured to constantly hold a voltage of an electrode in one frame.

[0065] The passivation layer 160 is arranged on the source 152 and the drain 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, which exposes the drain 154 of the thin film transistor Tr. Although the drain contact hole 162 is arranged on the second semiconductor layer contact hole 144, it can be spaced apart from the second semiconductor layer contact hole 144.

[0066] ​An organic light emitting diode (OLED) D includes a first electrode 210 disposed on the passivation layer 160 and connected with the drain 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 disposed in each pixel region. The first electrode 210 can be an anode and include 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), etc.

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

[0069] Further, to cover the edges 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 can be omitted.

[0070] The light emitting layer 230 is disposed on the first electrode 210. In one exemplary embodiment, the light emitting layer 230 can have a single layer structure of a light emitting material layer (EML). As an alternative, the light emitting layer 230 can have a multi-layer 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. 3 and 4 The light emitting layer 230 can have a single light emitting portion or a plurality of light emitting portions to form a tandem structure.

[0071] The light emitting layer 230 can include at least one light emitting material layer including at least one anthracene compound in which at least one hydrogen atom is substituted with tritium and a boron compound in a blue pixel area, and at least one electron blocking layer including an arylamine compound. Alternatively, the light emitting layer 230 can further include at least one hole blocking layer including at least one of an azine compound and a benzimidazole compound. The light emitting layer 230 can enable the OLED D and the organic light emitting display device 100 to significantly improve light emitting efficiency and light emitting lifespan thereof.

[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 on the entire display area, and can include a conductive material having a relatively low work function value compared to the first electrode 210, and can be a cathode. For example, the second electrode 220 can include, but is not limited to, a highly reflective material such as aluminum (Al), magnesium (Mg), calcium (Ca), silver (Ag), an alloy thereof, or a combination thereof, such as an aluminum magnesium alloy (Al-Mg). When the organic light emitting display device 100 is a top emission type, the second electrode 220 is thin such that it has light transmittance (semi-transparency).

[0073] Further, in order to prevent external moisture from penetrating the organic light emitting diode D, an encapsulation film 170 can be disposed on the second electrode 220, and the encapsulation film 170 can 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 can be omitted.

[0074] The organic light emitting display device 100 can further include a polarizing plate to reduce reflection of external light. For example, the polarizing plate can be a circular polarizing plate. When the organic light emitting display device 100 is a bottom emission type, the polarizing plate can be located below the substrate 102. Alternatively, when the organic light emitting display device 100 is a top emission type, the polarizing plate can be attached on the encapsulation film 170. Further, in the organic light emitting display device 100 of the top emission type, a cover window can be attached on the encapsulation film 170 or the polarizing plate. In this case, the substrate 102 and the cover window have flexibility, and thus a flexible display device can be constructed.

[0075] As described above, the light emitting layer 230 in the organic light emitting diode D includes a specific compound, and thus the organic light emitting diode D can improve light emitting efficiency and light emitting lifespan thereof. FIG. 3 FIG. 1 is a cross-sectional view illustrating an organic light emitting diode having a single light emitting portion according to one example embodiment of the present disclosure.

[0076] As FIG. 3As 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 opposite to 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, wherein 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] Furthermore, the light-emitting layer 230 may further include a HIL 310 disposed between the first electrode 210 and the EBL 330 and an HTL 320 disposed between the HIL 310 and the EBL 330. Furthermore, 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 ( FIG. 2 It includes red pixel areas, green pixel areas and blue pixel areas, and OLED D1 can be located in the blue pixel area.

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

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

[0080] [Formula 1A]

[0081]

[0082] Where R 11 To R 14 and R 21 To R 24 Each is independently selected from hydrogen, C1-C 10 Alkyl, C6-C 30 Aryl, C6-C 30 arylamino, C5-C 30 heteroaryl and C3-C 30 Groups composed of alicyclic groups, or R 11 To R 14 and R 21 To R 24 Two adjacent rings in the middle 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 unsubstituents or have at least one C1-C substituent. 10 Alkyl; R 31 and R 41 Each is independently selected from hydrogen, C1-C 10 Alkyl, C6-C 30 Aryl, C6-C 30 arylamino, C5-C 30 heteroaryl and C3-C 30 The group consisting of alicyclic groups, wherein R 31 and R 41 The aryl, arylamino, heteroaryl, and alicyclic groups are each independently unsubstituents or have at least one C1-C substituent. 10 Alkyl; R 51 Choose free 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 groups and C5-C 30 The group consisting of heterocyclic groups, where R 51 The cycloalkyl, aryl, arylamino, heteroaryl, alicyclic, and heterocyclic groups are each independently unsubstituent or have at least one C1-C substituent. 10 Alkyl; when R 31 R 41 and R 51 Each has at least one C1-C as a substitute 10 C6-C of alkyl groups 30 When aryl is used, the substituted alkyl groups are linked together to form a fused ring.

[0083] [Formula 1B]

[0084]

[0085] Where 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 Group composed of alicyclic groups; R 61 To R 64 Each is independently selected from hydrogen, C1-C 10 Alkyl, C6-C 30 Aryl, C6-C 30 arylamino, C5-C 30 heteroaryl and C3-C 30 Groups composed of alicyclic groups, or R 61 To R 64 Two adjacent rings in the middle form a fused ring, where R 61 To R 64 The aryl, arylamino, heteroaryl, and alicyclic groups are each independently unsubstituents or have at least one C1-C substituent. 10 Alkyl; R 71 To R 74 Each is independently selected from hydrogen, C1-C 10 Alkyl and C3-C 30 Group composed of alicyclic groups; R 81 Choose C6-C freely 30 Aryl, C5-C 30 heteroaryl and C3-C 30 Groups composed of alicyclic groups, or R 81 and R 61 Formation of fused rings, where R 81 The aryl, heteroaryl, and alicyclic groups are each independently unsubstituents or have at least one C1-C substituent. 10 Alkyl; R 82 Choose C6-C freely 30 Aryl, C5-C 30 heteroaryl and C3-C 30 The group consisting of alicyclic groups, wherein R 82 The aryl, heteroaryl, and alicyclic groups are each independently unsubstituents or have at least one C1-C substituent. 10 Alkyl; R 91 Choose free hydrogen, C1-C 10 Alkyl, C3-C 15 cycloalkyl, C6-C 30 Aryl, C6-C 30arylamino, C5-C 30 heteroaryl and C3-C 30 The group consisting of alicyclic groups, wherein R 91 The cycloalkyl, aryl, arylamino, heteroaryl, and alicyclic groups are each independently unsubstituent or have at least one C1-C substituent. 10 Alkyl; when R 81 R 82 and R 91 Each has at least one C1-C as a substitute 10 C6-C of alkyl groups 30 When aryl is used, the substituted alkyl groups are linked together to form a fused ring.

[0086] As an example, R in Equation 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, in which R 11 To R 14 R 21 To R 24 R 31 and R 41 The aryl and heteroaryl groups can each independently be unsubstituented or substituted with C1-C2 groups. 10 Alkyl group, and R in formula 1A 51 You can choose C1-C freely. 10 Alkyl, C6-C 30 arylamino, C5-C 30 heteroaryl and C3-C 30 A group composed of heterocyclic groups, wherein R 51 The heteroaryl, arylamino, and heterocyclic groups can each independently be unsubstituented or substituted with C1-C. 10 alkyl.

[0087] For example, in Equation 1A, R 11 To R 14 One of and / or R 21 To R 24 One of them could be C1-C 10 Alkyl groups, while R 11 To R 14 The remaining groups and / or R 21 To R 24 The remaining groups in can be hydrogen, and R 31 and R 41Each can independently replace C1-C 10 Alkyl groups with phenyl or substituted C1-C 10 Alkyl diphenylfuranyl. R in Formula 1A 51 It can be C1-C 10 Alkyl, diphenylamino, heteroaryl containing a nitrogen atom, or heterocyclic group containing a nitrogen atom. In this case, the alkyl group can be, but is not limited to, tert-butyl. Furthermore, the fused ring formed by adjacent groups can be, but is not limited to, C3-C. 10 Alicyclic ring.

[0088] Alternatively, X in Equation 1B can be O or S, and R in Equation 1B can be O or S. 61 To R 64 Each can be independently selected from hydrogen, C1-C 10 Alkyl and C6-C 30 The group consisting of aryl amino groups, or R 61 To R 64 Two adjacent rings in R can form a fused ring. 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 the C6-C. 30 Aryl and C5-C 30 Groups composed of heteroaryl groups, or R 81 and R 61 Fused rings can be formed, where R 81 The aryl and heteroaryl groups can each independently be unsubstituented or substituted with C1-C2 groups. 10 Alkyl, R 82 You can choose the C6-C. 30 Aryl and C5-C 30 The group consisting of heteroaryl groups, in which R 82 The aryl and heteroaryl groups can each independently be unsubstituented or substituted with C1-C2 groups. 10 Alkyl, and wherein R 91 Can be C1-C 10 alkyl.

[0089] For example, X in Equation 1B can be O. 61 To R 64 Each can independently choose protium, deuterium, and C1-C. 10 The group consisting of alkyl and diphenylamino, or R 61 To R 64 Two adjacent groups can form a fused ring, and the diphenylamino or fused group can be deuterated. 71 To R 74 Each can independently choose protium, deuterium, and C1-C. 10Groups composed of alkyl groups. R 81 and R 82 Each can be independently selected; each can be independently unsubstituented or substituted with deuterium and / or C1-C. 10 The group consisting of alkyl groups, phenyl groups, and dibenzofuranyl groups. R 91 It can be C1-C 10 Alkyl groups, such as tert-butyl, but not limited to these.

[0090] Alternatively, in Equation 1B, R 73 It can be C1-C 10 Alkyl, and R 71 R 72 and R 74 Each can be either protium or deuterium independently. For example, in boron compounds having the structure of Formula 1B, at least one protium atom can be substituted for deuterium, except for the aromatic ring bonded to the boron atom and two nitrogen atoms, and the aromatic ring fused with those heteroaromatic rings. That is, R in Formula 1B 91 It is not necessary to deuterate.

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

[0092] [Equation 2]

[0093]

[0094]

[0095] In another exemplary aspect, the body 344 of the anthracene compound may have the structure of Formula 3:

[0096] [Formula 3]

[0097]

[0098] Ar1 and Ar2 are each independently C6-C. 30 Aryl or C5-C 30 heteroaryl; L is a single bond, C6-C 20 aryl or C5-C 20 A heteroarylene; a is an integer from 0 to 8; b, c, and d are each independent integers 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 phenyl, naphthyl, dibenzofuranyl, or fused dibenzofuranyl, and L can be a single bond, phenylene, or dibenzofuranyl. For instance, in Formula 3, Ar1 can be naphthyl, dibenzofuranyl, or fused dibenzofuranyl, and Ar2 can be phenyl or naphthyl. Alternatively, both Ar1 and Ar2 can be naphthyl, and L can be a single bond, phenylene, or dibenzofuranyl.

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

[0101] For example, the body 344 of the anthracene compound can be selected from, but is not limited to, compounds of formula 4:

[0102] [Formula 4]

[0103]

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

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

[0106] Furthermore, when EML 340 includes a dopant 342 in which some or all of the protium linked to the aromatic rings and heteroaromatic rings other than the aromatic rings linked to boron atoms and two nitrogen atoms can be replaced by deuterium, the OLED D1 and organic light-emitting display device 100 can further improve their luminous efficiency and luminous lifetime.

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

[0108] HIL 310 is disposed between the first electrode 210 and HTL 320 and improves the interfacial properties between the inorganic first electrode 210 and the organic HTL 320. In an exemplary embodiment, 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-(naphthyl-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-tris(N-(naphthyl-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazolyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-di(1-naphthyl)-1,1'-biphenyl- 4,4”-Diamine (NPB; NPD), 1,4,5,8,9,11-hexaazatriphenylhexacarbonitrile (dipyrazine[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)polystyrene sulfonic acid (PEDOT / PSS), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl ether (F4TCNQ), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine and combinations thereof.

[0109] Alternatively, HIL 340 may comprise a hole injection host and a hole injection dopant. As an example, the hole injection host may comprise a spirofluorene compound having a structure of Formula 11, and the hole injection dopant may comprise an axialene compound having a structure of Formula 12, but is 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 can be, but is not limited to, from about 1 wt% to about 50 wt%, for example, from about 1 wt% to about 30 wt%. HIL 310 can be omitted if it meets the characteristics of OLEDD1.

[0115] HTL 320 is arranged between HIL 310 and EBL 330. In one exemplary embodiment, 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)) 3,5-Di(9H-carbazole-9-yl)-N,N-diphenylaniline (DCDPA), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl) N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine, N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine and / or spirofluorene compounds having the structure of Formula 11.

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

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

[0118] [Formula 5]

[0119]

[0120] L3 is C6-C 30 Aromatic; R 121 and R 122 Each is independently hydrogen, or R 121 and R 122 Two adjacent C 10 -C 20 Fused aryl or C 10 -C 20 Fused heteroaryl groups, wherein C 10 -C 20 Fused aryl and C 10 -C 20 Each of the fused heteroaryl groups may optionally be substituted with C1-C2. 10 Alkyl; R 123 Is it hydrogen or C6-C? 30 Aryl; R 124 It is C5-C 30 Heteroaryl; o is 0 or 1; p is a substituent R 121 The quantity is an integer from 0 to 4; and q is a substituent R. 122 The quantity is an integer between 0 and 5.

[0121] As an example, L3 can be phenylene, R 123 It can be hydrogen, phenyl, or biphenyl, and R 124 It can be carbazolyl, dibenzofuranyl, or dibenzothiophenel. R 121 and R 122 Each can be independently hydrogen, or R 121 and R 122 Two adjacent ones (e.g., 2 R) 121 and 2 R 122 , or R 121 and R 122 It can form naphthyl, C1-C 10 Alkyl-substituted fluorenyl, dibenzofuranyl and / or dibenzothiopheneyl.

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

[0123] [Formula 6]

[0124]

[0125]

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

[0127] [Formula 7]

[0128]

[0129] Among them, 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 Aromatic; R 132 It is C6-C 30 Aryl or C5-C 30 heteroaryl, of which C6-C 30 The aryl group can optionally be replaced by another C6-C. 30 Aryl or C5-C 30 Mixed aromatics, or with C 10 -C 30 Fused aryl rings or C 10 -C 30 The fused heteroaryl rings form a spirocyclic structure, in which another C6-C 30 The aryl group may optionally be further substituted with other C6-C groups. 30 Aryl or C5-C 30 Mixed aromatics, or with C 10 -C 30 Fused aryl rings form a spirocyclic structure; R 133 It is hydrogen, or two adjacent Rs 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 Aromatic; R 141 It is C6-C 30 Aryl or C5-C 30 heteroaryl, C6-C 30 Aryl and C5-C 30 Each of the heteroaryl groups may optionally be substituted with C1-C 10 Alkyl; and R 142 and R 143Each independently is hydrogen, C1-C 10 Alkyl or C6-C 30 Aryl.

[0133] In one exemplary implementation, R in Formula 7 132 The aryl group may be without substituents or further substituted with C6-C. 30 Aryl or C5-C 30 Heteroaryl, or formed with other fused aryl rings or fused heteroaryl rings into a spirocyclic structure. For example, it can be substituted into R. 132 The aryl or heteroaryl group can be C 10 -C 30 Fused aryl or C 10 -C 30 Dense heteroaryl groups. R in Formula 7 133 They can fuse to form naphthyl groups. In one exemplary embodiment, the azine compound used as hole-blocking material 352 can be selected from any azine compound having the structure of Formula 8:

[0134] [Formula 8]

[0135]

[0136]

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

[0138] [Formula 10]

[0139]

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

[0141] Compounds having structures of formulas 7 to 10 exhibit good electron transport properties and excellent hole blocking properties. Therefore, HBL 350, including compounds having structures of formulas 7 to 10, can serve as both 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, phenanthrene-rhein compounds, benzoxazole compounds, benzothiazole compounds, benzimidazole compounds, triazine compounds, etc.

[0143] In particular, the ETL may include electron transport materials 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, lithium hydroxyquinoline (Liq), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), di(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-yl) Aluminum hydroxyl (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4- Triazole (NTAZ), 1,3,5-tris(p-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), poly[9,9-di(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-anthrayl)phenyl]-1-phenyl-1H-benzimidazole (ZADN), 1,3-bis(9-phenyl-1,10-o-phenanthroline-2-yl)benzene, 1,4-bis(2-phenyl-1,10-o-phenanthroline-4-yl)benzene (p-bPPhenB) and / or 1,3-bis(2-phenyl-1,10-o-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 lifetime 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 (such as LiF, CsF, NaF and BaF2) and / or organometallic compounds (such as Liq, lithium benzoate and sodium stearate).

[0145] In another embodiment, EIL 360 may be an organic layer doped with alkali metals (such as Li, Na, K and / or Cs) and / or alkaline earth metals (such as Mg, Sr, Ba and / or Ra). The organic host used in EIL 360 may be an electron transport material, and the content of alkali metals and / or alkaline earth metals in EIL 360 may be, but is not limited to, from about 1% by weight to about 30% by weight. For example, 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 ETL and EIL 360 can each be independently from about 10nm to about 200nm, for example from about 10nm to 100nm.

[0149] The luminous efficiency and luminous lifetime of OLED D1 can be maximized by applying a dopant 342 of a boron compound having a structure of formula 1A to 2 and a body 344 of anthracene compound having a structure of formula 3 to 4 to EML 340, applying an arylamine compound having a structure of formula 5 and formula 6 to EBL 330, and optionally applying an azazine compound having a structure of formula 7 to 8 and / or a benzimidazole compound having a structure of formula 9 to 10 to HBL 350.

[0150] In a first exemplary embodiment, OLED D1 may have a single light-emitting element. The OLED of this disclosure may have a series structure comprising multiple light-emitting elements. FIG. 4 This is a schematic cross-sectional view showing an organic light-emitting diode having two light-emitting portions according to another exemplary embodiment of the present disclosure.

[0151] like FIG. 4As shown, the OLED D2 according to the second embodiment of this 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-generating layer (CGL) 470 disposed between the first light-emitting portion 400 and the second light-emitting portion 500. Organic light-emitting display device 100 ( FIG. 2 It includes red pixel areas, green pixel areas and blue pixel areas, and OLED D2 can be located in the blue pixel area.

[0152] One of the first electrode 210 and the second electrode 220 can be an anode, and the other of the first electrode 210 and the second electrode 220 can be a cathode. Alternatively, one of the first electrode 210 and the second electrode 220 can be a transmissive (semi-transmissive) electrode, and the other of the first electrode 210 and the second electrode 220 can 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 CGL 470. The first light-emitting portion 400 may include a first electron blocking layer (EBL1) 430 disposed between the first electrode 210 and EML1 440, and optionally a first hole blocking layer (HBL1) 450 disposed between EML1 440 and CGL 470. Furthermore, the first light-emitting portion 400 may further include a HIL 410 disposed between the first electrode 210 and EBL1 430, and a first hole transport layer (HTL1) 420 disposed between HIL 410 and EBL1 430.

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

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

[0156] The first dopant 442 and the second dopant 542 of the boron-based compounds 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 compounds 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 content of the first body 444 and the second body 544 in EML1 440 and EML2 540, respectively, can be independently from about 70% to about 99.9% by weight, and the content of the first dopant 442 and the second dopant 542 can be independently from about 0.1% to about 30% by weight. For example, the content of the first dopant 442 and the second dopant 542 in EML1 440 and EML2 540, respectively, can be from about 0.1% to about 10% by weight, for example, from about 1% to about 5% by weight, so that both EML1 440 and EML2 540 can achieve sufficient luminous efficiency and luminous lifetime.

[0158] EBL1 430 and EBL2 530 each prevent electrons from being transported from EML1 440 or EML2 540 to the first electrode 210 or CGL 470. EBL1 430 and EBL2 530 may each include a first electron-blocking material 432 and a second electron-blocking material 532. The first electron-blocking material 432 and the second electron-blocking material 532 may each independently include an amine compound having a structure of formula 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 prevent holes from being transported from EML1 440 or EML2 540 to CGL 470 or the second electrode 220. HBL1 450 and HBL2 550 may each include a first hole-blocking material 452 and a second hole-blocking material 552. The first hole-blocking material 452 and the second hole-blocking material 552 may each independently include an azazine compound having a structure of formula 7 to 8 and / or a benzimidazole compound having a structure of formula 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, compounds having structures of formulas 7 to 10 exhibit excellent electron transport properties and excellent hole blocking properties. Therefore, HBL1 450 and HBL2 550 can each serve as a hole blocking layer and an electron transport layer, respectively.

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

[0162] A CGL 470 is disposed between the first light-emitting part 400 and the second light-emitting part 500, such that the first light-emitting part 400 and the second light-emitting part 500 are connected by 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 HBL1 450 and HTL2 520, and the P-CGL 490 is disposed between the N-CGL 480 and HTL2 520. The N-CGL 480 injects electrons into the first light-emitting part 400, and the P-CGL 490 injects holes into the second light-emitting part 500.

[0163] As an example, N-CGL 480 can be an organic layer doped with alkali metals (such as Li, Na, K, and / or Cs) and / or alkaline earth metals (such as Mg, Sr, Ba, and / or Ra). For example, the organic host used in N-CGL 480 can include, but is not limited to, organic compounds such as Bphen or MTDATA. From about 0.01% to about 30% by weight of alkali metals and / or alkaline earth metals can be incorporated into N-type CGL 480.

[0164] P-CGL 490 may include, but is not limited to, tungsten oxide (WO3) x ), molybdenum oxide (MoO) xInorganic materials selected from the group consisting of beryllium oxide (Be2O3), vanadium oxide (V2O5), and combinations thereof, and / or organic materials selected from the group consisting of NPD, HAT-CN, F4TCNQ, TPD, N,N,N',N'-tetranaphthalene-benzidine (TNB), TCTA, N,N'-dioctyl-3,4,9,10-perylenedicarboximide (PTCDI-C8), and combinations thereof.

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

[0166] EML1 440 and EML2 540 each comprise 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. Furthermore, 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 indirectly connected to the anthracene moieties via linking groups, and at least one protium (e.g., all protium) is deuterated. Therefore, the OLED D2 and the organic light-emitting display device 100 can improve their luminous efficiency and luminous lifetime.

[0167] Furthermore, the OLED D2 and the organic light-emitting display device 100 can maximize their luminous efficiency and luminous lifetime by applying arylamine compounds having structures of formulas 5 and 6 as first and second electron blocking materials 432 and 532 to EBL1 430 and EBL2 530, respectively, and optionally applying azazine compounds having structures of formulas 7 to 8 and / or benzimidazole compounds having structures of formulas 9 to 10 as first hole blocking material 452 and second hole blocking material 552 to HBL1 450 and HBL2 550, respectively. Furthermore, the organic light-emitting display device 100 (see...) FIG. 2 High color purity images can be achieved by stacking two light-emitting parts 400 and 500 that each emit blue light in a double-stacked structure.

[0168] In the second embodiment, OLED D2 has a tandem structure of two light-emitting portions. Alternatively, the OLED may include more than three light-emitting portions; for example, it may include a second CGL and a third light-emitting portion arranged on the second light-emitting portion 500 other than EIL 560 (see...). FIG. 7 ).

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

[0170] like FIG. 5 As shown, the organic light-emitting display device 600 includes: a first substrate 602 defining 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 disposed between the first substrate 602 and the second substrate 604 and emitting white (W) light, and a color filter layer 680 disposed between the organic light-emitting diode D and the second substrate 604.

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

[0172] A buffer layer 606 may be disposed on the first substrate 602, and thin-film transistors Tr corresponding to the red pixel area RP, green pixel area GP, and blue pixel area BP are respectively disposed 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 disposed on the semiconductor layer 610, which includes an insulating material, such as an inorganic insulating material, like silicon oxide (SiO2). x ) or silicon nitride (SiN) x ).

[0175] A gate 630, made of a conductive material such as a metal, is disposed on a gate insulating layer 620, thereby corresponding to the center of the semiconductor layer 610. An interlayer insulating layer 640, comprising an insulating material such as an inorganic insulating material such as silicon oxide (SiO2), is disposed on the gate 630. x ) or silicon nitride (SiN) x ), or organic insulating materials such as benzocyclobutene or photopolymer acrylic.

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

[0178] Semiconductor layer 610, gate 630, source 652 and drain 654 constitute thin film transistor Tr, which acts as a driving element.

[0179] Although FIG. 5 Not shown, but intersecting gate lines and data lines defining the pixel area, as well as switching elements connected to the gate lines and data lines, can be further formed within the pixel area. The switching elements are connected to a thin-film transistor Tr, which serves as a driving element. Furthermore, power lines are parallel to and spaced from the gate lines or data lines, and the thin-film transistor Tr may further include a storage capacitor configured to maintain a constant voltage at the gate throughout a frame.

[0180] A passivation layer 660 is disposed on the source 652 and the drain 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 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 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 electrode 710 and the second electrode 720.

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

[0183] When the organic light-emitting display device 600 is a bottom-emitting type, the first electrode 710 may have a single-layer TCO structure. Alternatively, when the organic light-emitting display device 600 is a top-emitting 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 APC alloys. In the top-emitting 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 dam layer 664 is disposed on the passivation layer 660. Corresponding to the red pixel area RP, the green pixel area GP, and the blue pixel area BP respectively, the dam layer 664 exposes the center of the first electrode 710. The dam layer 664 can 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 the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP respectively, the light-emitting layer 730 can be formed by a common layer, instead of being divided into red pixel region RP, green pixel region GP, ​​and blue pixel region BP.

[0186] like FIG. 6 and FIG. 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-generating 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 HIL, HTL, EBL, HBL, ETL and / or EIL.

[0187] The second electrode 720 is disposed on the first substrate 602 on which the light-emitting layer 730 is arranged. The second electrode 720 may be disposed over the entire display area and may comprise a conductive material having a relatively low work function value compared to 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 of the second embodiment of this disclosure, since the 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 thinner thickness so that light can be transmitted.

[0189] A 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 respectively correspond to the red pixel area RP, the green pixel area GP, and the blue pixel area BP. Although in FIG. 5 Although not shown in the image, the color filter layer 680 can be bonded to the OLED using an adhesive layer. Alternatively, the color filter layer 680 can be directly disposed on the OLED D.

[0190] Furthermore, to prevent external moisture from penetrating the organic light-emitting diode D, an encapsulation film can 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. 2 (170 in the original text). Furthermore, the organic light-emitting display device 600 may further include a polarizing plate to reduce the 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 FIG. 5 In this configuration, light emitted from OLED D is transmitted through the second electrode 720, and a color filter layer 680 is disposed above OLED D. Alternatively, light emitted from OLED D is transmitted through the first electrode 710, and the color filter layer 680 can be disposed between OLED D and the first substrate 602. Furthermore, a color conversion layer can be formed between 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 disposed corresponding to a respective pixel region (RP, GP, and BP), thereby converting white (W) light into each of red, green, and blue light, respectively.

[0192] As described above, the white (W) light emitted from the OLED D is transmitted through a red filter 682, a green filter 684, and a blue filter 686. Each filter is set to correspond to the red pixel area RP, the green pixel area GP, and the blue pixel area BP, respectively, so that red, green, and blue light are displayed in the red pixel area RP, the green pixel area GP, and the blue pixel area BP.

[0193] FIG. 6 This is a schematic cross-sectional view showing an organic light-emitting diode (OLED) with two light-emitting portions. (See diagram below.)FIG. 6 As shown, an exemplary embodiment of an organic light-emitting diode (OLED) D3 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-generating 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 can be an anode, and the other of the first electrode 710 and the second electrode 720 can be a cathode. Alternatively, one of the first electrode 710 and the second electrode 720 can be a transmissive (semi-transmissive) electrode, and the other of the first electrode 710 and the second electrode 720 can be a reflective electrode.

[0195] Furthermore, 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. 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 below.

[0196] The first light-emitting part 800 includes an EML1 840 disposed between the first electrode 710 and CGL 870. The first light-emitting part 800 may include an EBL1 830 disposed between the first electrode 710 and EML1 840, and optionally an HBL1 850 disposed between EML1 840 and CGL 870. Furthermore, the first light-emitting part 800 may further include a HIL 810 disposed between the first electrode and EBL1 830, and an HTL1 820 disposed between HIL810 and EBL1 830. Alternatively, the first light-emitting part 800 may further include an ETL1 disposed between HBL1 850 and CGL 870.

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

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

[0199] HIL 810, HTL1 820, HTL2 920, EIL 560, and CGL 870 may each independently comprise the same materials as described above. HTL1 820 may comprise the same materials as HTL2 920 or different materials.

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

[0201] In one exemplary embodiment, in EML1 840, the content of the first body 844 can be from about 70% to about 99.9% by weight, and the content of the first dopant 842 can be from about 0.1% to about 30% by weight. For example, the content of the first dopant 844 in EML1 840 can be from about 0.1% to about 10% by weight, for example, from about 1% to about 5% by weight, so that EML1 840 can achieve sufficient luminous efficiency and luminous lifetime.

[0202] EBL1 830 prevents electrons from being transferred from 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 formula 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. The hole-blocking material 852 may include azazine compounds having structures of formulas 7 to 8 and / or benzimidazole compounds having structures of formulas 9 to 10. As described above, compounds having structures of formulas 7 to 10 have excellent electron transport properties and excellent hole-blocking properties. Therefore, HBL1 850 can serve as both a hole-blocking layer and an electron transport layer.

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

[0205] The main component 945 in EML2 940 may include, but is not limited to, 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (BCzPh), CBP, 1,3,5-tris(carbazole-9-yl)phenyl (TCP), TCTA, 4,4'-di(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), 2,7-di(carbazole-9-yl)-9,9-dimethylfluorene (DMFL-CBP), 2,2',7,7'-tetra(carbazole-9-yl)-9,9-spirofluorene (spiro-CBP), and di[2-(biphenylphosphine)]. [Phenyl] ether (DPEPO), 4'-(9H-carbazole-9-yl)biphenyl-3,5-dicarboxylonitrile (PCzB-2CN), 3'-(9H-carbazole-9-yl)biphenyl-3,5-dicarboxylonitrile (mCzB-2CN), 3,6-bis(carbazole-9-yl)-9-(2-ethylhexyl)-9H-carbazole (TCz1), bis(2-hydroxyphenyl)pyridine)beryllium (Bepp2), bis(10-hydroxybenzo[h]quinoline)beryllium (Bebq2) and / or 1,3,5-tris(1-pyrene)benzene (TPB3).

[0206] The yellow-green (YG) dopant 943 may include at least one of yellow-green (YG) fluorescent materials, yellow-green (YG) phosphorescent materials, and yellow-green (YG) delayed fluorescent materials. As examples, 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-diphenyl-tetraphenyl (TBRb), bis(2-phenylbenzothiazole)(acetylacetone)iridium(III)(Ir(BT)2(acac)), bis(2-(9,9-diethyl-fluorene-2-yl)-1-phenyl-1H-benzo[d]imidazol)(acetylacetone)iridium(III)(Ir(fbi)2(acac)), bis(2-phenylpyridine)(3-(pyridin-2-yl)-2H-chromene-2-one)iridium(III)(fac-Ir(ppy)2Pc), and bis(2-(2,4-difluorophenyl)quinoline)(pyridinecarboxylic acid)iridium(III)(FPQIrpic), etc.

[0207] Alternatively, the EML2 940 can emit red and green (RG) light. In this case, the EML2 940 may include green (G) and red (R) dopants 943 and a body 945. In this case, the EML2 940 may have a single-layer structure comprising the body, green (G) dopants, and red (R) dopants, or it may have a double-layer structure comprising: a lower layer (first layer) containing the body and green (G) dopants (or red (R) dopants), and an upper layer (second layer) containing the body and red (R) dopants (or green (G) dopants).

[0208] The main body 945 in the EML2 940 that emits red-green (RG) light can be the same as the main body that emits yellow-green (YG) light.

[0209] The green (G) dopant 943 in EML2 940 can include at least one of green fluorescent materials, green phosphorescent materials, and green delayed fluorescent materials. As examples, the green (G) dopant 943 can include, but is not limited to, [bis(2-phenylpyridine)](pyridine-2-benzofuran[2,3-b]pyridine)iridium, fac-tris(2-phenylpyridine)iridium(III) (fac-Ir(ppy)3), bis(2-phenylpyridine)(acetylacetone)iridium(III) (Ir(ppy)2(acac)), tris[2-(p-tolyl)pyridine]iridium(III) (Ir(mppy)3), bis(2-(naphthyl-2-yl)pyridine)(acetylacetone)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), etc.

[0210] The red (R) dopant 943 in EML2 940 can include at least one of red fluorescent materials, red phosphorescent materials, and red delayed fluorescent materials. As examples, the red (R) dopant 943 can include, but is not limited to, [bis(2-(4,6-dimethyl)phenylquinoline)](2,2,6,6-tetramethylhept-3,5-dione)iridium(III), bis[2-(4-n-hexylphenyl)quinoline](acetylacetone)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), and bis(phenylisoquinoline)(2,2,6,6-tetramethyl... Examples of iridium(III)[(4-hexylphenyl)isoquinoline](acetylacetone)iridium(III)[(Hex-Ir(piq)2(acac))], tris[2-(4-hexylphenyl)quinoline]iridium(III)[(Hex-Ir(piq)3)], tris[2-(3-methylphenyl)-7-methylquinoline]iridium(Ir(dmpq)3], di[2-(2-methylphenyl)-7-methylquinoline](acetylacetone)iridium(III)[Ir(dmpq)2(acac)], di[2-(3,5-dimethylphenyl)-4-methylquinoline](acetylacetone)iridium(III)[Ir(mphmq)2(acac)], etc.

[0211] Alternatively, the EML2 940 can have a three-layer structure, with the first layer consisting of a host and a red (R) dopant, the second layer consisting of a host and a yellow-green (YG) dopant, and the third layer consisting of 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 main component 945 in the EML2 940 can be from about 70% to about 99.9% by weight, and the content of the dopant 943 can be from about 0.01% to about 30% by weight. For example, the content of the dopant 943 in the EML2 940 can be from about 0.1% to about 10% by weight, such as from about 1% to about 5% by weight, so that the EML2 940 can achieve sufficient luminous efficiency and luminous lifetime.

[0213] ETL1 and ETL2 950 may each independently include oxazole compounds, triazole compounds, phenanthrene-rhein compounds, benzoxazole compounds, benzothiazole compounds, benzimidazole compounds, triazine compounds, etc. For example, ETL1 and ETL2 950 may each independently include electron transport materials 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-o-phenanthroline-2-yl)benzene, p-bPPhenB, m-bPPhenB, and combinations thereof.

[0214] The EBL2, which can be positioned between HTL2 920 and 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 formula 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-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, TAPC, MTDATA, 1,3-di(carbazole-9-yl)phenyl (mCP), 3,3-di(9H-carbazole-9-yl)biphenyl (mCBP), CuPc, DNTPD, TDAPB, DCDPA, 2,8-di(9-phenyl-9H-carbazole-3-yl)dibenzo[b,d]thiophene, 3,6-di(N-carbazole)-N-phenyl-carbazole, and combinations thereof.

[0216] The HBL2, which can be located between EML2 940 and ETL2 960, may include a second hole-blocking material. As an example, the second hole-blocking material may include azazine compounds having a structure of formula 7 to 8 and / or benzimidazole compounds having a structure of formula 9 to 10. Alternatively, HBL2 may include oxadiazole compounds, triazole compounds, phenanthrene-rhein compounds, benzoxazole compounds, benzothiazole compounds, benzimidazole compounds, triazine compounds, etc., which can be used as electron transport materials in ETL2 950.

[0217] In OLED D3, EML1 840 includes a boron dopant 842 and an anthracene compound body 844 in which at least one protium is replaced by 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 boron dopant 842 and an anthracene compound body 844 to emit blue (B) light.

[0218] In the OLED D3, EML1 840 comprises a boron-based dopant 842 and a body 844 of an at least partially deuterated anthracene compound. The boron-based dopant 842 may have an asymmetric chemical structure as shown in Formula 1B, and may be undeuterated or partially deuterated. Furthermore, the anthracene compound body 844 may have a structure in which two naphthyl moieties are directly or indirectly linked to the anthracene moieties, and at least one protium (e.g., all protium) is deuterated. Therefore, the OLED D3 and the organic light-emitting display device 600 can have improved luminous efficiency and luminous lifetime.

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

[0220] Alternatively, organic light-emitting diodes can have more than three light-emitting parts. FIG. 7 This is a schematic cross-sectional view depicting an organic light-emitting diode according to another exemplary aspect of this disclosure. FIG. 7 As shown, the organic light-emitting diode (OLED) D4 includes a first electrode 710 and a second electrode 720 opposite to 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-generating layer (CGL1) 1070 disposed between the first light-emitting portion 1000 and the second light-emitting portion 1100, and a second charge-generating 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 can emit blue (B) light, and at least another of the first to third light-emitting portions 1000, 1100, and 1200 can emit red-green (RG) or yellow-green (YG) light. The OLED D4 will now be described in detail, wherein the first light-emitting portion 1000 and the third light-emitting portion 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 EML 11040 disposed between the first electrode 710 and CGL1 1070. The first light-emitting portion 1000 may include an EBL 11030 disposed between the first electrode 710 and EML1 1040, and optionally an HBL 1050 disposed between EML11040 and CGL1 1070. Furthermore, the first light-emitting portion 1000 may further include a HIL 1010 disposed between the first electrode 710 and EBL1 1030, an HTL 1020 disposed between HIL 1010 and EBL1 1030, and optionally a first electron transport layer (ETL 1) disposed between HBL 11050 and CGL1 1070.

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

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

[0225] CGL1 1070 is disposed between the first light-emitting part 1000 and the second light-emitting part 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 part 1000, and P-CGL1 1090 injects holes into the second light-emitting part 1100.

[0226] CGL2 1170 is disposed between the second light-emitting part 1100 and the third light-emitting part 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 1080 is disposed between ETL2 11150 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 part 1100, and P-CGL2 1190 injects holes into the third light-emitting part 1200.

[0227] HIL 1010, HTL1 1020, HTL2 1120, HTL3 1130, EIL 120, CGL1 10170, and CGL2 1170 may each independently comprise the same material as described above. HTL1 1020, HTL2 1120, and HTL3 1220 may each comprise the same material or different materials from each other. Furthermore, CGL1 1070 may comprise the same material as CGL2 1170 or a different material.

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

[0229] The first dopant 1042 and the second dopant 1242 of the boron-based compounds 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 compounds 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, in EML1 1040 and EML3 1240, the contents of the first body 1044 and the second body 1244 can each be independently about 70% to about 99.9% by weight, and the contents of the first dopant 1042 and the second dopant 1242 can each be independently about 0.1% to about 30% by weight. For example, the contents of the first dopant 1042 and the second dopant 1242 in EML1 1040 and EML3 1240 can be about 0.1% to about 10% by weight, for example, about 1% to about 5% by weight, so that both EML1 1040 and EML3 1240 can achieve sufficient luminous efficiency and luminous lifetime.

[0231] EBL1 1030 and EBL3 1230 can each prevent electrons from being transferred from EML1 1040 or EML3 1240 to the first electrode 710 or CGL2 1170, respectively. EBL1 1030 and EBL3 1230 can each 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 formula 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 transported from EML1 1040 or EML3 1240 to CGL11070 or the second electrode 720. HBL1 1050 and HBL3 1250 may each include a first hole-blocking material 1052 and a third hole-blocking material 1252. The first hole-blocking material 1052 and the third hole-blocking material 1252 may each independently include an azazine compound having a structure of formula 7 to 8 and / or a benzimidazole compound having a structure of formula 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, compounds having structures of formulas 7 to 10 exhibit 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, respectively.

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

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

[0236] Alternatively, EML2 1140 can have a three-layer structure: the first layer comprises a host and a red (R) dopant, the second layer comprises a host and a yellow-green (YG) dopant, and the third layer comprises a host and a green (G) dopant. Dopant 1143 and host 1145 in EML2 1140 can be referenced above. FIG. 6 The corresponding materials described are the same.

[0237] ETL1, ETL2 1150, ETL3, EBL2 disposed between HTL2 1120 and EML2 1140, and HBL2 disposed between EML2 1140 and ETL2 1150 may each comprise the same compound as the corresponding material described above.

[0238] EML1 1040 and EML3 1240 each comprise 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 wherein 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. Furthermore, 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 indirectly connected to the anthracene moieties via linking groups, and at least one protium (e.g., all protium) is deuterated. Therefore, the OLED D4 and the organic light-emitting display device 600 can improve their luminous efficiency and luminous lifetime.

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

[0240] exist FIG. 7 The image depicts an OLED D4 with a tandem structure of three light-emitting portions. Alternatively, the OLED may further include at least one other light-emitting portion and at least one other charge-generating layer.

[0241] Furthermore, the organic light-emitting device disclosed herein may include a color conversion layer. FIG. 8 This is a schematic cross-sectional view depicting an organic light-emitting display device in another exemplary embodiment of the present disclosure.

[0242] like FIG. 8 As 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 disposed between the first substrate 1302 and the second substrate 1304 and emitting blue (B) light, and a color conversion layer 1380 disposed between the OLED D and the second substrate 1304. Although in FIG. 8 It is not shown, but a color filter layer can be arranged between the second substrate 1304 and each color conversion layer 1380.

[0243] A thin-film transistor Tr is disposed on a 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 over the entire first substrate 1302 covering the thin-film transistor Tr, which has a drain contact hole 1362 to expose an electrode (e.g., the drain) constituting the thin-film transistor Tr.

[0244] An OLED D, comprising a first electrode 1410, a light-emitting layer 1430, and a second electrode 1420, is disposed on a passivation layer 1360. The first electrode 1410 can be connected to the drain of a thin-film transistor Tr through a drain contact hole 1362. Furthermore, a dam layer 1364 is formed at the boundary between the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP, covering the edge of the first electrode 1410. In this configuration, the OLED D can have… FIG. 3 or FIG. 4 The OLED has a structure that allows it to emit blue (B) light. The OLED is arranged in red pixel regions RP, green pixel regions GP, and blue pixel regions BP to provide blue (B) light.

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

[0246] Blue (B) light emitted from 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 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 color images.

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

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

[0249] (1) Synthetic 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 added to a 500 ml reaction vessel, and the solution was refluxed with 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 give 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 added to 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 gas was purged 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 complete, an aqueous sodium acetate 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 give compound 1-1 (2.3 g, yield: 20%).

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

[0258] (1) Synthetic intermediate 1-4C

[0259] [Reaction 2-1]

[0260]

[0261] Compounds 1-4A (43.1 g, 98 mmol), 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 added to a 500 ml reaction vessel, and the solution was refluxed with 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 give intermediate 1-4C (57.1 g, yield: 85%).

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

[0263] [Reaction 2-2]

[0264]

[0265] Intermediate 1-4C (8.6 g, 12.5 mmol) and tert-butylbenzene (60 mL) were added to 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 gas was purged 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 complete, an aqueous sodium acetate 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 give compound 1-4 (1.9 g, yield: 23%).

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

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

[0268] [Reaction 3-1]

[0269]

[0270] Compounds 1-6A (58.9 g, 98 mmol), 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 added to a 500 ml reaction vessel, and the solution was refluxed with 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 give intermediate 1-6C (59.7 g, yield: 75%).

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

[0272] [Reaction 3-2]

[0273]

[0274] Intermediate 1-6C (10.1 g, 12.5 mmol) and tert-butylbenzene (60 mL) were added to 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 gas was purged 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 complete, an aqueous sodium acetate 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 give compound 1-6 (1.9 g, yield: 21%).

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

[0276] (1) Synthetic intermediate 1-8C

[0277] [Reaction 4-1]

[0278]

[0279] Compounds 1-8A (33.0 g, 98 mmol), 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 added to a 500 ml reaction vessel, and the solution was refluxed with 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 give intermediate 1-8C (54.1 g, yield: 72%).

[0280] (2) Synthesize compounds 1-8

[0281] [Reaction 4-2]

[0282]

[0283] Intermediate 1-8C (9.6 g, 12.5 mmol) and tert-butylbenzene (60 mL) were added to 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 gas was purged 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 complete, an aqueous sodium acetate 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 give compound 1-8 (2.0 g, yield: 21%).

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

[0285] (1) Synthetic intermediate 1-11C

[0286] [Reaction 5-1]

[0287]

[0288] Compounds 1-11A (28.4 g, 98 mmol), 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 added to a 500 ml reaction vessel, and the solution was refluxed with 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 give intermediate 1-11C (39.9 g, yield: 52%).

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

[0290] [Reaction 5-2]

[0291]

[0292] Intermediate 1-11C (9.8 g, 12.5 mmol) and tert-butylbenzene (60 mL) were added to 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 gas was purged 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 complete, an aqueous sodium acetate 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 give compound 1-11 (1.4 g, yield: 15%).

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

[0294] (1) Synthetic intermediate 1-12C

[0295] [Reaction 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 added to a 500 ml reaction vessel, and the solution was refluxed with 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 give intermediate 1-12C (44.1 g, yield: 58%).

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

[0299] [Reaction 6-2]

[0300]

[0301] Intermediate 1-12C (9.7 g, 12.5 mmol) and tert-butylbenzene (60 mL) were added to 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 gas was purged 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 complete, an aqueous sodium acetate 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 give compound 1-12 (1.7 g, yield: 18%).

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

[0303] (1) Synthetic intermediate 1-13C

[0304] [Reaction Formula 7-1]

[0305]

[0306] Compounds 1-13A (34.8 g, 98 mmol), 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 added to a 500 ml reaction vessel, and the solution was refluxed with 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 give intermediate 1-13C (41.3 g, yield: 53%).

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

[0308] [Reaction 7-2]

[0309]

[0310] Intermediate 1-13C (9.9 g, 12.5 mmol) and tert-butylbenzene (60 mL) were added to 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 gas was purged 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 complete, an aqueous sodium acetate 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 give compound 1-13 (1.4 g, yield: 15%).

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

[0312] (1) Synthetic intermediate 1-17C

[0313] [Reaction Equation 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 added to a 500 ml reaction vessel, and the solution was refluxed with 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 give intermediate 1-17C (47.1 g, yield: 62%).

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

[0317] [Reaction Equation 8-2]

[0318]

[0319] Intermediate 1-17C (9.7 g, 12.5 mmol) and tert-butylbenzene (60 mL) were added to 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 gas was purged 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 complete, an aqueous sodium acetate 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 give 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(dibenzylacetone)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 removed from the drying oven, and anhydrous sodium carbonate (2 M, 20 ml) was added to the solution. The reaction mixture was stirred and heated overnight at 90 °C. The reaction was monitored by HPLC (high performance liquid chromatography). After cooling the solution 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 a white powder of compound 2-1 (2.3 g, yield: 86%).

[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 reaction mixture was stirred and heated overnight at 90 °C. The reaction was monitored by HPLC. After cooling the solution 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 a white powder of compound 2-2 (2.0 g, yield: 89%).

[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 reaction mixture was stirred and heated overnight at 90 °C. The reaction was monitored by HPLC. After cooling the solution 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 a white powder of compound 2-3 (2.0 g, yield: 79%).

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

[0333] [Reaction 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 reaction mixture was stirred and heated overnight at 90 °C. The reaction was monitored by HPLC. After cooling the solution 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 a white powder of compound 2-4 (2.0 g, yield: 67%).

[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 added to 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 reaction mixture was stirred and heated overnight at 90 °C. The reaction was monitored by HPLC. After cooling the solution 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 a white powder of compound 2-5 (2.0 g, yield: 81%).

[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 added to 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 reaction mixture was stirred and heated overnight at 90 °C. The reaction was monitored by HPLC. After cooling the solution 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 a white powder of compound 2-6 (2.0 g, yield: 81%).

[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 under a nitrogen atmosphere to a solution of compound 2-1 (5.0 g, 9.9 mmol) dissolved in per-deuterated benzene (100 mL). The resulting mixture was stirred at RT for 6 hours, and then D2O (50 mL) was added to the mixture. After separation of the organic and aqueous layers, the aqueous layer was washed with dichloromethane (30 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 give 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 under a nitrogen atmosphere to a solution of compound 2-2 (5.0 g, 11.6 mmol) dissolved in per-deuterated benzene (120 mL). The resulting mixture was stirred at RT for 6 hours, and then D2O (70 mL) was added to the mixture. After separation of the organic and aqueous layers, 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 give compound 2-8 (4.0 g, yield: 76%) as a white powder.

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

[0353] [Reaction Formula 17]

[0354]

[0355] Aluminum chloride (0.9 g, 4.3 mmol) was added under a nitrogen atmosphere to a solution of compound 2-3 (5.0 g, 11.9 mmol) dissolved in per-deuterated benzene (120 mL). The resulting mixture was stirred at RT for 6 hours, and then D2O (70 mL) was added to the mixture. After separation of the organic and aqueous layers, 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 give 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 under a nitrogen atmosphere to a solution of compound 2-4 (5.0 g, 10.1 mmol) dissolved in per-deuterated benzene (120 mL). The resulting mixture was stirred at RT for 6 hours, and then D2O (70 mL) was added to the mixture. After separation of the organic and aqueous layers, 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 give 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 under a nitrogen atmosphere to a solution of compound 2-5 (5.0 g, 10.6 mmol) dissolved in per-deuterated benzene (120 mL). The resulting mixture was stirred at RT for 6 hours, and then D2O (70 mL) was added to the mixture. After separation of the organic and aqueous layers, 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 give compound 2-11 (4.0 g, yield: 77%) as a white powder.

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

[0365] [Reaction 20]

[0366]

[0367] Aluminum chloride (0.9 g, 4.3 mmol) was added under a nitrogen atmosphere to a solution of compound 2-6 (5.0 g, 10.6 mmol) dissolved in per-deuterium benzene (120 mL). The resulting mixture was stirred at RT for 6 hours, and then D2O (70 mL) was added to the mixture. After separation of the organic and aqueous layers, 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 give compound 2-12 (4.3 g, yield: 82%) as a white powder.

[0368] Manufacture of an organic light emitting diode (OLED)

[0369] A glass substrate (40mm × 40mm × 0.5mm) coated with a thin film of ITO was washed with solvents such as isopropanol, acetone, and distilled water, and ultrasonically cleaned for 5 minutes, then dried in an oven at 100°C. After cleaning, 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 approximately 5 to 7 × 10⁻⁶ mm... - 7 Under Torr, through evaporation from the heated boat, to The deposition rate is such that the light-emitting layer and the cathode are deposited in the following order:

[0370] HIL (Formula 11 (97 wt%) and Formula 12 (3 wt%), ); HTL (Formula 11, EBL EML (body (H, 98 wt%) and dopant (D, 2 wt%), HBL EIL (Formula 13 (98 wt%), Li (2 wt%), ); and cathode (Al, ).

[0371] Then, the OLED is encapsulated with UV-curable epoxy resin and a moisture-proofing agent.

[0372] Comparative Example 1 (Ref. 1): Manufacture of an OLED

[0373] An OLED was manufactured in which the EBL includes the following Ref. EBL, the EML includes compound 1-1 (dopant) and compound 2-1 (body) of Formula 2, and the HBL includes the following Ref. HBL.

[0374] Example 1-9 (Ex. 1-9): Manufacture of an OLED

[0375] The OLED is manufactured in which the EML contains compounds 1-1 (dopant) of Formula 2 and compounds 2-7 (body) of Formula 4, the EBL contains the following Ref. EBL (Ex. 1-3), H21 (Ex. 4-6) of Formula 6 or H23 (Ex. 7-9) of Formula 6, and the HBL contains the following Ref. HBL (Ex. 1, 4 and 7), E1 (Ex. 2, 5 and 8) of Formula 8 or F1 (Ex. 3, 6 and 9) of Formula 10.

[0376] [Reference Compound]

[0377]

[0378] Experimental Example 1: Measurement of light emitting properties of an OLED

[0379] The 9mm-sized samples manufactured in Examples 1 to 9 and Comparative Example 1 2 Each OLED with a specific luminescent area was connected to an external power supply, and the luminescent characteristics of all OLEDs were evaluated at room temperature using a constant current source (KEITHLEY) and a PR650 photometer. Specifically, the evaluation was conducted at a current density of 10 mA / cm². 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 duration (T) during which the brightness decreases from the initial brightness to 95%. 95 The measurement results are shown in Table 1 below.

[0380] Table 1: Light emitting properties of an OLED

[0381]

[0382] Comparative Example 2 (Ref. 2): Manufacture of an OLED

[0383] Manufacturing an OLED, wherein the EBL comprises Ref.EBL, the EML comprises compound 1-1 (dopant) and compound 2-3 (body) of Formula 2, and the HBL comprises Ref.HBL.

[0384] Example 10-18 (Ex. 10-18): Manufacture of an OLED

[0385] The OLED is manufactured in which the EML contains compounds 1-1 (dopant) of Formula 2 and compounds 2-9 (body) of Formula 4, the EBL contains Ref. EBL (Ex. 10-12), H21 (Ex. 13-15) of Formula 6 or H23 (Ex. 16-18) of Formula 6, and the HBL contains Ref. HBL (Ex. 10, 13 and 16), E1 (Ex. 11, 14 and 17) of Formula 8 or F1 (Ex. 12, 15 and 18) of Formula 10.

[0386] Experimental Example 2: Measurement of light emitting properties of an OLED

[0387] The luminescence characteristics of each OLED manufactured in Examples 10-18 and Comparative Example 2 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 2 below.

[0388] Table 2: Light emitting properties of an OLED

[0389]

[0390] Comparative Example 3 (Ref. 3): Manufacture of an OLED

[0391] Manufacturing an OLED, wherein the EBL comprises Ref.EBL, the EML comprises compounds 1-4 (dopers) and compound 2-1 (body) of Formula 2, and the HBL comprises Ref.HBL.

[0392] Example 19-27 (Ex. 19-27): Manufacture of an OLED

[0393] The OLED is manufactured in which the EML contains compounds 1-4 (dopers) of Formula 2 and compounds 2-7 (body) of Formula 4, the EBL contains Ref. EBL (Ex. 19-21), H21 (Ex. 22-24) of Formula 6 or H23 (Ex. 25-27) of Formula 6, and the HBL contains Ref. HBL (Ex. 19, 22 and 25), E1 (Ex. 20, 23 and 26) of Formula 8 or F1 (Ex. 21, 24 and 27) of Formula 10.

[0394] Experimental Example 3: Measurement of light emitting properties of an OLED

[0395] The luminescence characteristics of each OLED manufactured in Examples 19-27 and Comparative Example 3 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 3 below.

[0396] Table 3: Light emitting properties of an OLED

[0397]

[0398] Comparative Example 4 (Ref. 4): Manufacture of an OLED

[0399] Manufacturing an OLED, wherein the EBL comprises Ref.EBL, the EML comprises compounds 1-4 (dopers) and compounds 2-3 (host) of Formula 2, and the HBL comprises Ref.HBL.

[0400] Example 28-36 (Ex. 28-36): Manufacture of an OLED

[0401] The OLED is manufactured in which the EML contains compounds 1-4 (dopersants) of Formula 2 and compounds 2-9 (body) of Formula 4, the EBL contains Ref. EBL (Ex. 28-30), H21 (Ex. 31-33) of Formula 6 or H23 (Ex. 34-36) of Formula 6, and the HBL contains Ref. HBL (Ex. 28, 31 and 34), E1 (Ex. 29, 32 and 35) of Formula 8 or F1 (Ex. 30, 33 and 36) of Formula 10.

[0402] Experimental Example 4: Measurement of light emitting properties of an OLED

[0403] The luminescence characteristics of each OLED manufactured in Examples 28-36 and Comparative Example 4 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 4 below.

[0404] Table 4: Light emitting properties of an OLED

[0405]

[0406] Comparative Example 5 (Ref. 5): Manufacture of an OLED

[0407] Manufacturing an OLED, wherein the EBL comprises Ref.EBL, the EML comprises compounds 1-6 (dopers) and compound 2-1 (body) of Formula 2, and the HBL comprises Ref.HBL.

[0408] Example 37-45 (Ex. 37-45): Manufacture of an OLED

[0409] The OLED is manufactured in which the EML contains compounds 1-6 (dopersants) of Formula 2 and compounds 2-7 (body) of Formula 4, the EBL contains Ref. EBL (Ex. 37-39), H21 (Ex. 40-42) of Formula 6 or H23 (Ex. 43-45) of Formula 6, and the HBL contains Ref. HBL (Ex. 37, 40 and 43), E1 (Ex. 38, 41 and 44) ​​of Formula 8 or F1 (Ex. 39, 42 and 45) of Formula 10.

[0410] Experimental Example 5: Measurement of light emitting properties of an OLED

[0411] The luminescence properties of each OLED manufactured in Examples 37-45 and Comparative Example 5 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 5 below.

[0412] Table 5: Light emitting properties of an OLED

[0413] Sample EBL D H HBL V EQE (%) CIE (x) CIE (y) T 95 (hr) Ref. 5 Ref. 1-6 2-1 Ref. 3.93 3.11 0.140 0.076 26 Ex. 37 Ref. 1-6 2-7 Ref. 3.95 3.09 0.140 0.075 45 Ex. 38 Ref. 1-6 2-7 E1 3.95 3.14 0.141 0.074 54 Ex. 39 Ref. 1-6 2-7 F1 3.91 3.19 0.140 0.075 61 Ex. 40 H21 1-6 2-7 Ref. 3.89 6.74 0.140 0.076 90 Ex. 41 H21 1-6 2-7 E1 3.83 6.90 0.140 0.074 118 Ex. 42 H21 1-6 2-7 F1 3.80 7.02 0.140 0.074 137 Ex. 43 H23 1-6 2-7 Ref. 3.87 6.13 0.140 0.076 94 Ex. 44 H23 1-6 2-7 E1 3.82 6.27 0.140 0.074 124 Ex. 45 H23 1-6 2-7 F1 3.82 6.38 0.140 0.074 142

[0414] Comparative Example 6 (Ref. 6): Manufacture of an OLED

[0415] Manufacturing an OLED, wherein the EBL comprises Ref.EBL, the EML comprises compounds 1-6 (dopers) and compounds 2-3 (host) of Formula 2, and the HBL comprises Ref.HBL.

[0416] Example 46-54 (Ex. 46-54): Manufacture of an OLED

[0417] The OLED is manufactured in which the EML contains compounds 1-6 (dopersants) of Formula 2 and compounds 2-9 (body) of Formula 4, the EBL contains Ref. EBL (Ex. 46-48), H21 (Ex. 49-51) of Formula 6 or H23 (Ex. 52-54) of Formula 6, and the HBL contains Ref. HBL (Ex. 46, 49 and 52), E1 (Ex. 47, 50 and 53) of Formula 8 or F1 (Ex. 48, 51 and 54) of Formula 10.

[0418] Experimental Example 6: Measurement of light emitting properties of an OLED

[0419] The luminescence characteristics of each OLED manufactured in Examples 46-54 and Comparative Example 6 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 6 below.

[0420] Table 6: Light emitting properties of an OLED

[0421] Sample EBL D H HBL V EQE (%) CIE (x) CIE (y) T 95 (hr) Ref. 6 Ref. 1-6 2-3 Ref. 3.82 3.01 0.139 0.076 28 Ex. 46 Ref. 1-6 2-9 Ref. 3.84 3.03 0.138 0.081 38 Ex. 47 Ref. 1-6 2-9 E1 3.81 3.09 0.137 0.080 49 Ex. 48 Ref. Ref. 1-6 2-9 F1 3.82 3.19 0.138 0.081 58 Ex. 49 H21 1-6 2-9 Ref. 3.77 6.66 0.140 0.078 82 Ex. 50 H21 1-6 2-9 E1 3.70 6.74 0.137 0.081 106 Ex. 51 H21 1-6 2-9 F1 3.71 6.94 0.137 0.082 128 Ex. 52 H23 1-6 2-9 Ref. 3.76 6.13 0.138 0.079 86 Ex. 53 H23 1-6 2-9 E1 3.72 6.13 0.138 0.079 112 Ex. 54 H23 1-6 2-9 F1 3.71 6.31 0.137 0.082 134

[0422] Comparative Example 7 (Ref. 7): Manufacture of an OLED

[0423] Manufacturing an OLED, wherein the EBL comprises Ref.EBL, the EML comprises compounds 1-8 (dopers) and compound 2-1 (body) of Formula 2, and the HBL comprises Ref.HBL.

[0424] Examples 55-63 (Ex. 55-63): Manufacture of an OLED

[0425] The OLED is manufactured in which the EML contains compounds 1-8 (dopersants) of Formula 2 and compounds 2-7 (hosts) of Formula 4, the EBL contains Ref. EBL (Ex. 55-57), H21 (Ex. 58-60) of Formula 6 or H23 (Ex. 61-63) of Formula 6, and the HBL contains Ref. HBL (Ex. 55, 58 and 61), E1 (Ex. 56, 59 and 62) of Formula 8 or F1 (Ex. 57, 60 and 63) of Formula 10.

[0426] Experimental Example 7: Measurement of the light-emitting properties of an OLED

[0427] The luminescence characteristics of each OLED manufactured in Examples 55-63 and Comparative Example 7 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 7 below.

[0428] Table 7: Light-emitting properties of an OLED

[0429] Sample EBL D H HBL V EQE (%) CIE (x) CIE (x) T 95 (hr) Ref. 7 Ref. 1-8 2-1 Ref. 3.92 3.12 0.136 0.081 28 Ex. 55 Ref. 1-8 2-7 Ref. 3.93 3.08 0.139 0.082 42 Ex. 56 Ref. 1-8 2-7 E1 3.87 3.17 0.137 0.081 50 Ex. 57 Ref. 1-8 2-7 F1 3.91 3.22 0.137 0.082 59 Ex. 58 H21 1-8 2-7 Ref. 3.83 6.78 0.138 0.081 87 Ex. 59 H21 1-8 2-7 E1 3.80 6.92 0.137 0.080 109 Ex. 60 H21 1-8 2-7 F1 3.81 7.08 0.137 0.081 128 Ex. 61 H23 1-8 2-7 Ref. 3.83 6.17 0.137 0.082 91 Ex. 62 H23 1-8 2-7 E1 3.79 6.29 0.138 0.081 115 Ex. 63 H23 1-8 2-7 F1 3.83 6.44 0.136 0.082 135

[0430] Comparative Example 8 (Ref. 8): Manufacture of an OLED

[0431] Manufacturing an OLED, wherein the EBL comprises Ref.EBL, the EML comprises compounds 1-8 (dopers) and compounds 2-3 (host) of Formula 2, and the HBL comprises Ref.HBL.

[0432] Examples 64-72 (Ex. 64-72): Manufacture of an OLED

[0433] The OLED is manufactured in which the EML contains compounds 1-8 (dopants) of Formula 2 and compounds 2-9 (body) of Formula 4, the EBL contains Ref. EBL (Ex. 64-66), H21 (Ex. 67-69) of Formula 6 or H23 (Ex. 70-72) of Formula 6, and the HBL contains Ref. HBL (Ex. 64, 67 and 70), E1 (Ex. 65, 68 and 71) of Formula 8 or F1 (Ex. 66, 69 and 72) of Formula 10.

[0434] Experimental Example 8: Measurement of the light-emitting properties of an OLED

[0435] The luminescence characteristics of each OLED manufactured in Examples 64-72 and Comparative Example 8 were measured using the same procedure as in Experimental Example 1. The measurement results are shown in Table 8 below.

[0436] Table 8: Light-emitting properties of an OLED

[0437] Sample EBL D H HBL V EQE (%) CIE (x) CIE (y) T 95 (hr) Ref. 8 Ref. 1-8 2-3 Ref. 3.80 3.05 0.137 0.081 27 Ex. 64 Ref. 1-8 2-9 Ref. 3.81 3.07 0.138 0.083 36 Ex. 65 Ref. 1-8 2-9 E1 3.76 3.06 0.137 0.083 42 Ex. 66 Ref. 1-8 2-9 F1 3.80 3.18 0.137 0.083 52 Ex. 67 H21 1-8 2-9 Ref. 3.74 6.56 0.138 0.081 78 Ex. 68 H21 1-8 2-9 E1 3.69 6.73 0.136 0.084 97 Ex. 69 H21 1-8 2-9 F1 3.73 6.93 0.137 0.082 115 Ex. 70 H23 1-8 2-9 Ref. 3.73 6.05 0.137 0.083 82 Ex. 71 H23 1-8 2-9 E1 3.69 6.12 0.136 0.084 102 Ex. 72 H23 1-8 2-9 F1 3.71 6.30 0.137 0.083 120

[0438] Summarizing the results in Tables 1 to 8, compared with OLEDs manufactured in Ref. 1 to Ref. 8 in which the EML includes non-deuterated anthracene compounds (compound 2-1 or compound 2-3) as the main components, OLEDs manufactured in Ex. 1 to Ex. 72 in which the EML includes deuterated anthracene compounds (compound 2-7 or compound 2-9) as the main components, have improved luminous efficiency and luminous lifetime.

[0439] Furthermore, compared to OLEDs manufactured in Ex.1-9, 19-27, 37-45, and 55-63, where the EML contains compounds 2-9 as the main component, OLEDs manufactured in Ex.1-9, 19-27, 37-45, and 55-63, where the EML contains compounds 2-7 as the main component, exhibit improved luminous efficiency and lifetime. In other words, when the naphthyl moiety (1-naphthyl) is directly attached to one side of the anthracene moiety and another naphthyl moiety (2-naphthyl) is directly or via a bridging group (linking group) attached to the other side of the anthracene moiety and is used as the main component in the EML by a deuterated anthracene compound, the luminous efficiency and lifetime of the OLED are further improved.

[0440] Furthermore, when boron compounds with asymmetric chemical structures (compounds 1-6 or 1-8) are used as dopants 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...) is used as a dopant, the luminous efficiency and luminous lifetime of the OLED are further improved. 91 It is alkyl (tert-butyl), R 81 and R 82 When aryl (phenyl) groups, each substituted with an alkyl group (tert-butyl), are used as dopants in the EML, the luminous efficiency and luminous lifetime of the OLED are significantly improved.

[0441] Furthermore, when the HBL includes an azazine compound of formula 8 or a benzimidazole compound of formula 10, the OLED exhibits excellent luminous efficiency and luminous lifetime. Additionally, when the HBL includes an amine compound of formula 6, the luminous efficiency and luminous lifetime of the OLED can be maximized.

[0442] Furthermore, when the EML includes deuterated anthracene compounds (compounds 2-7 or 2-9) and boron compounds of formula 1B, the EBL includes amine compounds of formula 5, and the HBL includes azazine compounds of formula 7 or benzimidazole compounds of formula 9, the luminous efficiency and luminous lifetime of the OLED are significantly improved.

[0443] It will be apparent to those skilled in the art that various modifications and variations can be made to this disclosure without departing from its scope. Therefore, this disclosure is intended to cover such modifications and variations as long as they fall within the scope of the appended claims.

Claims

1. An organic light-emitting device, comprising: substrate; and An organic light-emitting diode (OLED) is mounted on the substrate, the OLED 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 monolayer of first light-emitting material containing a first dopant and a first host, and a first electron-blocking layer disposed between the first electrode and the first light-emitting material layer. The first dopant includes a boron compound having the structure of Formula 1B. The first main body consists only of anthracene compounds having the structure of Formula 3, and The first electron-blocking layer comprises an amine compound having the structure of Formula 5: [Formula 1B] Where 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 Group composed of alicyclic groups; R 61 To R 64 Each is independently selected from hydrogen, C1-C 10 Alkyl, C6-C 30 Aryl, C6-C 30 arylamino, C5-C 30 heteroaryl and C3-C 30 Groups composed of alicyclic groups, or R 61 To R 64 Two adjacent rings in the middle form a fused ring, where R 61 To R 64 The aryl, arylamino, heteroaryl, and alicyclic groups are each independently unsubstituents or have at least one C1-C substituent. 10 Alkyl; R 71 To R 74 Each is independently selected from hydrogen, C1-C 10 Alkyl and C3-C 30 Group composed of alicyclic groups; R 81 Choose C6-C freely 30 Aryl, C5-C 30 heteroaryl and C3-C 30 Groups composed of alicyclic groups, or R 81 and R 61 Formation of fused rings, where R 81 The aryl, heteroaryl, and alicyclic groups are each independently unsubstituents or have at least one C1-C substituent. 10 Alkyl; R 82 Choose C6-C freely 30 Aryl, C5-C 30 heteroaryl and C3-C 30 The group consisting of alicyclic groups, wherein R 82 The aryl, heteroaryl, and alicyclic groups are each independently unsubstituents or have at least one C1-C substituent. 10 Alkyl; R 91 Choose free 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 The group consisting of alicyclic groups, wherein R 91 The cycloalkyl, aryl, arylamino, heteroaryl, and alicyclic groups are each independently unsubstituent or have at least one C1-C substituent. 10 Alkyl; when R 81 R 82 and R 91 Each has at least one C1-C as a substitute 10 C6-C of alkyl groups 30 In the case of aryl groups, the substituted alkyl groups are linked together to form a fused ring; [Formula 3] Ar1 and Ar2 are each independently C6-C. 30 Aryl or C5-C 30 heteroaryl; L is a single bond, C6-C 20 aryl or C5-C 20 A heteroarylene; a is an integer from 0 to 8; b, c, and d are each independent integers from 0 to 30, wherein at least one of a, b, c, and d is a positive integer; [Formula 5] L3 is C6-C 30 Aromatic; R 121 and R 122 Each is independently hydrogen, or R 121 and R 122 Two adjacent C 10 -C 20 Fused aryl or C 10 -C 20 Fused heteroaryl groups, wherein the C 10 -C 20 Fused aryl and the C 10 -C 20 Each fused heteroaryl group is independently unsubstituent or has C1-C substituents. 10 Alkyl; R 123 Is it hydrogen or C6-C? 30 Aryl; R 124 It is C5-C 30 Heteroaryl; o is 0 or 1; p is a substituent R 121 The quantity is an integer from 0 to 4; q is a substituent R. 122 The quantity is an integer between 0 and 5.

2. The organic light-emitting device as described in claim 1, wherein, In Equation 1B, X is O or S, where R in Equation 1B 61 To R 64 Each is independently selected from hydrogen, C1-C 10 Alkyl and C6-C 30 The group consisting of aryl amino groups, or R 61 To R 64 Two adjacent rings in the middle form a fused ring, where R 71 To R 74 Each is independently selected from hydrogen and C1-C 10 The group consisting of alkyl groups, wherein R 81 Choose C6-C freely 30 Aryl and C5-C 30 Groups composed of heteroaryl groups, or R 81 and R 61 Forming a fused ring, wherein R 81 The aryl and heteroaryl groups are each independently unsubstituents or have C1-C substituents. 10 Alkyl, wherein R 82 Choose C6-C freely 30 Aryl and C5-C 30 The group consisting of heteroaryl groups, in which R 82 The aryl and heteroaryl groups are each independently unsubstituents or have C1-C substituents. 10 Alkyl group, wherein R 91 For C1-C 10 alkyl.

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

4. The organic light-emitting device as described in claim 1, wherein, The first component is selected from the following anthracene compounds:

5. The organic light-emitting device as claimed in claim 1, wherein, The amine compounds are selected from the following amine compounds:

6. The organic light-emitting device as claimed in 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 as claimed in claim 6, wherein, The first hole-blocking layer comprises at least one of an azazine compound having the structure of Formula 7 and a benzimidazole compound having the structure of Formula 9: [Formula 7] Among them, 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 Aromatic; R 132 It is C6-C 30 Aryl or C5-C 30 Heteroaryl, wherein the C6-C 30 The aryl group either does not have a substituent independently or the substituent has another C6-C. 30 Aryl or C5-C 30 Mixed aromatics, or with C 10 -C 30 Fused aryl rings or C 10 -C 30 The fused heteroaryl rings form a spirocyclic structure, wherein the other C6-C 30 The aryl group independently does not have substituents or further substitutions with other C6-C groups. 30 Aryl or C5-C 30 Mixed aromatics, or with C 10 -C 30 Fused aryl rings form a spirocyclic structure; R 133 It is hydrogen, or two adjacent Rs 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 Aromatic; R 141 It is C6-C 30 Aryl or C5-C 30 Heteroaryl, the C6-C 30 Aryl and the C5-C 30 Each heteroaryl group is independently unsubstituent or has C1-C substituents. 10 Alkyl; and R 142 and R 143 Each independently is hydrogen, C1-C 10 Alkyl or C6-C 30 Aryl.

8. The organic light-emitting device as claimed in claim 7, wherein, The acridine compounds are selected from the following acridine compounds:

9. The organic light-emitting device as claimed in claim 7, wherein, The benzimidazole compounds are selected from the following benzimidazole compounds:

10. The organic light-emitting device as claimed in claim 1, wherein, The light-emitting layer further includes a single-layer second light-emitting material layer disposed between the first light-emitting material layer and the second electrode, and a first charge-generating layer disposed between the first light-emitting material layer and the second light-emitting material layer.

11. The organic light-emitting device as claimed in claim 10, wherein, The second luminescent material layer comprises a second dopant and a second host, wherein the second dopant comprises a boron compound having a structure of Formula 1B, and wherein the second host consists only of an anthracene compound having a structure of Formula 3.

12. The organic light-emitting device as claimed in claim 10, wherein, The light-emitting layer further includes a second electron-blocking layer disposed between the first charge-generating layer and the second light-emitting material layer, wherein the second electron-blocking layer comprises an amine compound having the structure of Formula 5.

13. The organic light-emitting device as claimed in 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-generating 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 as claimed in claim 10, wherein, The light-emitting layer further includes: a single-layer third light-emitting material layer disposed between the second light-emitting material layer and the second electrode, and a second charge-generating layer disposed between the second light-emitting material layer and the third light-emitting material layer.

15. The organic light-emitting device as claimed in claim 1, wherein, The substrate defines a red pixel area, a green pixel area, and a blue pixel area, and the organic light-emitting diode is correspondingly located in the red pixel area, the green pixel area, and the blue pixel area. The organic light-emitting device further includes a color conversion layer, which corresponds to the red pixel area and the green pixel area and is disposed between the substrate and the organic light-emitting diode or above the organic light-emitting diode.

16. The organic light-emitting device as claimed in claim 10, wherein, The second luminescent material layer emits yellow-green or red-green light.

17. The organic light-emitting device as claimed in claim 14, wherein, The second luminescent material layer emits yellow-green or red-green light.

18. The organic light-emitting device as claimed in claim 16, wherein, The substrate defines a red pixel area, a green pixel area, and a blue pixel area, and the organic light-emitting diode is 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 disposed between the substrate and the organic light-emitting diode or above the organic light-emitting diode.

19. The organic light-emitting device as claimed in claim 17, wherein, The substrate defines a red pixel area, a green pixel area, and a blue pixel area, and the organic light-emitting diode is 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 disposed between the substrate and the organic light-emitting diode or above the organic light-emitting diode.

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