organic light-emitting devices

Abstract

The present disclosure relates to an organic light-emitting device, comprising: a substrate; and an organic light-emitting diode, which is located on the substrate and includes: a first electrode; a second electrode facing the first electrode; a first light-emitting material layer, the first light-emitting material layer containing a first dopant of a boron derivative and a first host of an anthracene derivative and located between the first electrode and the second electrode; a first electron blocking layer, the first electron blocking layer containing an electron blocking material of an amine derivative and located between the first electrode and the first light-emitting material layer; and a first hole blocking layer, the first hole blocking layer containing a hole blocking material and located between the second electrode and the first light-emitting material layer, wherein the first host is deuterated.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of Korean Patent Application No. 10-2020-0184956, filed in Korea on December 28, 2020, which is hereby incorporated by reference in its entirety. Technical Field

[0003] The present disclosure relates to an organic light emitting device, and more particularly, to an organic light emitting diode (OLED) having enhanced luminous efficiency and lifespan, and an organic light emitting device including the same. Background Art

[0004] As demand for flat panel display devices having a small footprint increases, organic light emitting display devices including OLEDs have become the subject of recent research and development.

[0005] OLED emits light by injecting electrons from the cathode as an electron injection electrode and holes from the anode as a hole injection electrode into the light-emitting material layer (EML), combining the electrons with the holes to generate excitons, and converting the excitons from the excited state to the ground state. Flexible substrates, such as plastic substrates, can be used as base substrates for forming elements. In addition, organic light-emitting display devices can operate at a lower voltage (for example, below 10V) than the voltage required to operate other display devices. In addition, organic light-emitting display devices have advantages in power consumption and color perception.

[0006] The OLED includes a first electrode as an anode over a substrate, a second electrode spaced apart from and facing the first electrode, and an organic light emitting layer therebetween.

[0007] For example, the organic light emitting display device may include a red pixel region, a green pixel region, and a blue pixel region, and an OLED may be formed in each of the red pixel region, the green pixel region, and the blue pixel region.

[0008] However, the OLED in the blue pixel cannot provide sufficient luminous efficiency and lifespan, so that the OLED display device is limited in luminous efficiency and lifespan. Summary of the Invention

[0009] The present disclosure relates to an OLED and an organic light emitting device including the same that substantially obviate one or more problems associated with limitations and disadvantages of related conventional technologies.

[0010] Other features and advantages of the present disclosure are set forth in the following description and will become apparent from the description or be understood through the practice of the present disclosure. The objects and other advantages of the present disclosure are realized and obtained by the features described herein and in the accompanying drawings.

[0011] To achieve these and other advantages consistent with the objectives of the embodiments of the present disclosure, as described herein, one aspect of the present disclosure is an organic light-emitting device comprising: a substrate; and an organic light-emitting diode, the organic light-emitting diode being located on the substrate and comprising: a first electrode; a second electrode facing the first electrode; a first light-emitting material layer comprising a first dopant of a boron derivative and a first host of an anthracene derivative and being located between the first electrode and the second electrode; a first electron blocking layer comprising an electron blocking material and being located between the first electrode and the first light-emitting material layer; and a first hole blocking layer comprising a hole blocking material and being located between the second electrode and the first light-emitting material layer, wherein the first dopant is represented by Formula 1:

[0012] [Formula 1]

[0013]

[0014] wherein X is one of NR1, CR2R3, O, S, Se, SiR4R5, and R1, R2, R3, R4 and R5 are each independently selected from hydrogen, C1 to C 10 Alkyl, C6 to C 30 Aryl, C5 to C 30 Heteroaryl, C3 to C 30 Cycloalkyl and C3 to C 30 A group consisting of alicyclic groups,

[0015] Among them, R 61 to R 64 are each independently selected from hydrogen, deuterium, C1 to C2 which are unsubstituted or substituted with deuterium. 10 Alkyl, unsubstituted or substituted with deuterium and C1 to C 10 At least one of the C6 to C 30 Aryl, unsubstituted or substituted with deuterium and C1 to C 10 At least one of the C6 to C 30 Arylamino, unsubstituted or substituted with deuterium and C1 to C 10 At least one of the C5 to C 30 Heteroaryl and unsubstituted or substituted with deuterium and C1 to C 10 At least one of the C3 to C 30 A group consisting of alicyclic groups, or R 61 to R 64 Two adjacent ones are connected to form a fused ring.

[0016] Among them, R 71 to R 74 Each independently selected from hydrogen, deuterium, C1 to C 10 Alkyl and C3 to C30 A group consisting of alicyclic groups,

[0017] Among them, R 81 Selected from the group consisting of no substituent or substituted with deuterium and C1 to C 10 At least one of the C6 to C 30 Aryl, unsubstituted or substituted with deuterium and C1 to C 10 At least one of the C5 to C 30 Heteroaryl and unsubstituted or substituted with deuterium and C1 to C 10 At least one of the C3 to C 30 Alicyclic group, or with R 61 Connected to form a fused ring,

[0018] Among them, R 82 Selected from the group consisting of no substituent or substituted with deuterium and C1 to C 10 At least one of the C6 to C 30 Aryl, unsubstituted or substituted with deuterium and C1 to C 10 At least one of the C5 to C 30 Heteroaryl and unsubstituted or substituted with deuterium and C1 to C 10 At least one of the C3 to C 30 A group consisting of alicyclic groups,

[0019] Among them, R 91 Selected from hydrogen, C1 to C 10 Alkyl, unsubstituted or substituted with C1 to C 10 C3 to C 15 Cycloalkyl, unsubstituted or substituted with C1 to C 10 Alkyl C6 to C 30 Aryl, unsubstituted or substituted with C1 to C 10 Alkyl C5 to C 30 Heteroaryl, unsubstituted or substituted with C1 to C 10 Alkyl C6 to C 30 Arylamino and unsubstituted or substituted with C1 to C 10 C3 to C 30 A group consisting of alicyclic groups,

[0020] Among them, when R 81 、R 82 and R 91 Each is substituted with C1 to C 10 Alkyl C6 to C 30 When it is an aryl group, these alkyl groups are connected to form a fused ring.

[0021] Among them, the first entity is expressed by formula 2:

[0022] [Formula 2]:

[0023]

[0024] wherein Ar1 and Ar2 are each independently C6 to C 30 Aryl or C5 to C 30 heteroaryl, and L is a single bond or C6 to C 30 an arylene group, wherein a is an integer from 0 to 8, b, c and d are each independently an integer from 0 to 30, wherein at least one of a, b, c and d is a positive integer,

[0025] Wherein, the electron blocking material is represented by Formula 3:

[0026] [Formula 3]

[0027]

[0028] Wherein, in Formula 3, R1, R2 and R4 are each independently selected from the group consisting of a monocyclic aryl group or a polycyclic aryl group, R3 is a monocyclic arylene group or a polycyclic arylene group, and at least one of R1, R2, R3 and R4 is polycyclic.

[0029] 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 disclosure as claimed. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] The accompanying drawings are included to provide a further understanding of the disclosure and are incorporated in and constitute a part of this application, illustrate embodiments of the disclosure and together with the description serve to explain the principle of the disclosure.

[0031] Figure 1 is a schematic circuit diagram illustrating an organic light emitting display device of the present disclosure.

[0032] Figure 2 is a schematic cross-sectional view illustrating an organic light emitting display device according to a first embodiment of the present disclosure.

[0033] Figure 3 is a schematic cross-sectional view illustrating an OLED having a single emission portion for an organic light emitting display device according to a first embodiment of the present disclosure.

[0034] Figure 4 is a schematic cross-sectional view illustrating an OLED having a tandem structure of two emission parts according to a first embodiment of the present disclosure.

[0035] Figure 5 is a schematic cross-sectional view illustrating an organic light emitting display device according to a second embodiment of the present disclosure.

[0036] Figure 6 is a schematic cross-sectional view illustrating an OLED having a tandem structure of two emission parts according to a second embodiment of the present disclosure.

[0037] Figure 7 is a schematic cross-sectional view illustrating an OLED having a tandem structure of three emission parts according to a second embodiment of the present disclosure.

[0038] Figure 8 is a schematic cross-sectional view illustrating an organic light emitting display device according to a third embodiment of the present disclosure. DETAILED DESCRIPTION

[0039] Reference will now be made in detail to some examples and preferred embodiments which are illustrated in the accompanying drawings.

[0040] Figure 1 is a schematic circuit diagram illustrating an organic light emitting display device of the present disclosure.

[0041] like Figure 1 As shown, in an organic light-emitting display device, gate lines GL, data lines DL, and power lines PL are formed to intersect with each other to define pixels (pixel regions) P. A switching thin film transistor (TFT) Ts, a driving TFT Td, a storage capacitor Cst, and an OLED D are formed in the pixels P. The pixels P may include red pixels, green pixels, and blue pixels.

[0042] A switching thin film transistor Ts is connected to a gate line GL and a data line DL. A driving thin film transistor Td and a storage capacitor Cst are connected between the switching thin film transistor Ts and a power line PL. An OLED D is connected to the driving thin film transistor Td. When a gate signal applied via the gate line GL turns on the switching thin film transistor Ts, a data signal applied via the data line DL is applied to the gate electrode of the driving thin film transistor Td and one electrode of the storage capacitor Cst through the switching thin film transistor Ts.

[0043] The driving thin-film transistor Td is turned on by a data signal applied to its gate electrode, allowing a current proportional to the data signal to flow from the power line PL through the driving thin-film transistor Td to the OLED D. The OLED D emits light with a brightness proportional to the current flowing through the driving thin-film transistor Td. In this state, the storage capacitor Cst is charged with a voltage proportional to the data signal, maintaining a constant voltage at the gate electrode of the driving thin-film transistor Td during one frame. As a result, the organic light-emitting display device can display a desired image.

[0044] Figure 2 is a schematic cross-sectional view illustrating an organic light emitting display device according to a first embodiment of the present disclosure.

[0045] like Figure 2 As shown, the organic light-emitting display device 100 includes a substrate 110, a TFT Tr, and an OLED D connected to the TFT Tr. For example, the organic light-emitting display device 100 may include a red pixel, a green pixel, and a blue pixel, and an OLED D may be formed in each of the red pixel, the green pixel, and the blue pixel. That is, an OLED D emitting red light, green light, and blue light may be provided in the red pixel, the green pixel, and the blue pixel, respectively.

[0046] The substrate 110 may be a glass substrate or a flexible substrate. For example, the flexible substrate may be one of a polyimide (PI) substrate, polyethersulfone (PES), polyethylene naphthalate (PEN), polyethylene terephthalate (PET), and polycarbonate (PC).

[0047] The buffer layer 120 is formed on the substrate, and the TFT Tr is formed on the buffer layer 120. The buffer layer 120 may be omitted.

[0048] A semiconductor layer 122 is formed on the buffer layer 120. The semiconductor layer 122 may include an oxide semiconductor material or polysilicon.

[0049] When the semiconductor layer 122 includes an oxide semiconductor material, a light shielding pattern (not shown) may be formed below the semiconductor layer 122. Light entering the semiconductor layer 122 is shielded or blocked by the light shielding pattern, thereby preventing thermal degradation of the semiconductor layer 122. On the other hand, when the semiconductor layer 122 includes polycrystalline silicon, impurities may be doped into both sides of the semiconductor layer 122.

[0050] A gate insulating layer 124 is formed on the semiconductor layer 122. The gate insulating layer 124 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride.

[0051] A gate 130 formed of a conductive material such as metal is formed on the gate insulating layer 124 corresponding to the center of the semiconductor layer 122 .

[0052] exist Figure 2 In the embodiment of the present invention, the gate insulating layer 124 is formed on the entire surface of the substrate 110. Alternatively, the gate insulating layer 124 may be patterned to have the same shape as the gate 130.

[0053] An interlayer insulating layer 132 formed of an insulating material is formed on the gate electrode 130. The interlayer insulating layer 132 may be formed of an inorganic insulating material (eg, silicon oxide or silicon nitride) or an organic insulating material (eg, benzocyclobutene or photo acryl).

[0054] The interlayer insulating layer 132 includes a first contact hole 134 and a second contact hole 136 that expose both sides of the semiconductor layer 122. The first contact hole 134 and the second contact hole 136 are located on both sides of the gate 130 and are spaced apart from the gate 130.

[0055] The first and second contact holes 134 and 136 are formed through the gate insulating layer 124. Alternatively, when the gate insulating layer 124 is patterned to have the same shape as the gate 130, the first and second contact holes 134 and 136 are formed through only the interlayer insulating layer 132.

[0056] A source electrode 140 and a drain electrode 142 formed of a conductive material such as metal are formed on the interlayer insulating layer 132 .

[0057] The source electrode 140 and the drain electrode 142 are spaced apart from each other relative to the gate electrode 130 and contact two sides of the semiconductor layer 122 through the first contact hole 134 and the second contact hole 136 , respectively.

[0058] The semiconductor layer 122, the gate electrode 130, the source electrode 140, and the drain electrode 142 constitute a TFT Tr. The TFT Tr serves as a driving element. That is, the TFT Tr may correspond to the driving TFT Td ( Figure 1 ).

[0059] In the TFT Tr, the gate electrode 130, the source electrode 140, and the drain electrode 142 are located above the semiconductor layer 122. That is, the TFT Tr has a coplanar structure.

[0060] Alternatively, in the TFT Tr, the gate electrode may be located below the semiconductor layer, and the source electrode and the drain electrode may be located above the semiconductor layer, so that the TFT Tr may have an inverted staggered structure. In this case, the semiconductor layer may include amorphous silicon.

[0061] Although not shown, the gate lines and the data lines cross each other to define pixels, and a switching TFT is formed to be connected to the gate lines and the data lines. The switching TFT is connected to a TFT Tr as a driving element.

[0062] In addition, a power supply line (which may be formed parallel to and spaced apart from one of the gate line and the data line) and a storage capacitor for maintaining a voltage of the gate electrode of the TFT Tr in one frame may be further formed.

[0063] A passivation layer (or planarization layer) 150 is formed to cover the TFT Tr, and includes a drain contact hole 152 exposing the drain electrode 142 of the TFT Tr.

[0064] A first electrode 160 connected to the drain electrode 142 of the TFT Tr through the drain contact hole 152 is formed separately in each pixel and on the passivation layer 150. The first electrode 160 may be an anode and may be formed of a conductive material having a relatively high work function, such as a transmissive conductive oxide (TCO). For example, the first electrode 160 may be formed of indium tin oxide (ITO), indium zinc oxide (IZO), indium tin zinc oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium copper oxide (ICO), or aluminum zinc oxide (Al:ZnO, AZO).

[0065] When the organic light-emitting display device 100 operates in a bottom-emission mode, the first electrode 160 may have a single-layer structure of a transmissive conductive oxide. When the organic light-emitting display device 100 operates in a top-emission mode, a reflective electrode or reflective layer may be formed below the first electrode 160. For example, the reflective electrode or reflective layer may be formed of silver (Ag) or an aluminum-palladium-copper (APC) alloy. In this case, the first electrode 160 may have a three-layer structure of ITO / Ag / ITO or ITO / APC / ITO.

[0066] The bank layer 166 is formed on the planarization layer 150 to cover the edge of the first electrode 160. That is, the bank layer 166 is located at the boundary of the pixel and exposes the center of the first electrode 160 in the pixel.

[0067] The organic light emitting layer 162 is formed on the first electrode 160. The organic light emitting layer 162 may include an emission material layer (EML) including an emission material, an electron blocking layer (EBL) between the first electrode 160 and the EML, and a hole blocking layer (HBL) between the EML and the second electrode 164.

[0068] Organic light-emitting layer 162 is separated in each of the red, green, and blue pixels. As shown below, organic light-emitting layer 162 in the blue pixel includes a host of an anthracene derivative (anthracene compound) in which at least a portion of hydrogen is substituted with deuterium (deuterated), and a dopant of a boron derivative (boron compound), thereby improving the luminous efficiency and lifespan of the OLED D in the blue pixel.

[0069] Furthermore, in the OLED D, the EBL includes an amine derivative having or substituted with a polycyclic aromatic group, and the HBL includes at least one of an azine derivative and a benzimidazole derivative as hole blocking materials. Consequently, the lifespan of the OLED D and the organic light-emitting display device 100 is further improved.

[0070] The second electrode 164 is formed above the substrate 110 on which the organic light-emitting layer 162 is formed. The second electrode 164 covers the entire surface of the display area and can be formed of a conductive material having a relatively low work function to function as a cathode. For example, the second electrode 164 can be formed of aluminum (Al), magnesium (Mg), silver (Ag), or alloys thereof, such as an Al-Mg alloy (AlMg) or an Ag-Mg alloy (MgAg). In a top-emission organic light-emitting display device 100, the second electrode 164 can have a thin profile (small thickness) to provide transmissive characteristics (or semi-transmissive characteristics).

[0071] The first electrode 160 , the organic light emitting layer 162 , and the second electrode 164 constitute an OLED D.

[0072] The encapsulation film 170 is formed on the second electrode 164 to prevent moisture from penetrating into the OLED D. The encapsulation film 170 includes a first inorganic insulating layer 172 , an organic insulating layer 174 , and a second inorganic insulating layer 176 sequentially stacked, but is not limited thereto. The encapsulation film 170 may be omitted.

[0073] The organic light-emitting display device 100 may further include a polarizing plate (not shown) for reducing ambient light reflection. For example, the polarizing plate may be a circular polarizing plate. In a bottom-emission organic light-emitting display device 100, the polarizing plate may be disposed below the substrate 110. In a top-emission organic light-emitting display device 100, the polarizing plate may be disposed on or above the encapsulation film 170.

[0074] In addition, in the top emission type organic light emitting display device 100, a cover window (not shown) may be attached to the packaging film 170 or the polarizing plate. In this case, the substrate 110 and the cover window have flexibility, thereby providing a flexible organic light emitting display device.

[0075] Figure 3 is a schematic cross-sectional view illustrating an OLED having a single emission portion of an organic light emitting display device according to a first embodiment of the present disclosure.

[0076] like Figure 3 As shown, the OLED D includes a first electrode 160 and a second electrode 164 facing each other and an organic light emitting layer 162 therebetween. The organic light emitting layer 162 includes an EML 240 between the first electrode 160 and the second electrode 164, an EBL 230 between the first electrode 160 and the EML 240, and an HBL between the EML 240 and the second electrode 164. The organic light emitting display device 100 ( Figure 2 ) includes a red pixel, a green pixel and a blue pixel, and the OLED D can be positioned in the blue pixel.

[0077] One of the first electrode 160 and the second electrode 164 is an anode, and the other is a cathode. One of the first electrode 160 and the second electrode 164 is a transmissive electrode (or a semi-transmissive electrode), and the other is a reflective electrode.

[0078] The organic light emitting layer 162 may further include a hole transport layer (HTL) 220 between the first electrode 160 and the EBL 230 .

[0079] In addition, the organic light emitting layer 162 may further include a hole injection layer (HIL) 210 between the first electrode 160 and the HTL 220 and an electron injection layer (EIL) 260 between the second electrode 164 and the HBL 250 .

[0080] For example, the HTL 210 may include at least one compound selected from 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-(naphthalene-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazolyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-

[0066] In some embodiments, the HIL 210 may include a compound of Formula 12 as a host and a compound of Formula 13 as a dopant.

[0081] The HTL 220 may include at least one compound selected from the group consisting of N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), NPB (or NPD), 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), bis[4-(N,N-di-p-tolylamino)-phenyl] cyclohexane (TAPC), 3,5-bis(9H-carbazolyl-9-yl)-N,N-diphenylaniline (DCDPA), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, and N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl-4-amine. Alternatively, HTL 220 may include the compound of Formula 12.

[0082] The EIL 260 may include an alkali metal such as Li, an alkali metal halide such as LiF, CsF, NaF, or BaF2, and an organometallic compound such as Liq, lithium benzoate, or sodium stearate, but is not limited thereto. Alternatively, the EIL 260 may include the compound of Formula 14 as a host and an alkali metal as a dopant.

[0083] EML 240 includes a dopant 242 of a boron derivative and a host 244 of a deuterated anthracene derivative, providing blue emission. Specifically, at least one hydrogen atom in the anthracene derivative is replaced with deuterium, and is referred to as a deuterated anthracene derivative. A boron derivative, which has no deuterium replacement or partially replaced hydrogen atoms, is referred to as a non-deuterated boron derivative or a partially deuterated boron derivative.

[0084] In the EML 240 , the host 244 is partially or fully deuterated, while the dopant 242 is non-deuterated or partially deuterated.

[0085] The boron derivative as the dopant 242 may be represented by Formula 1-1 or 1-2.

[0086] [Formula 1-1]

[0087]

[0088] [Formula 1-2]

[0089]

[0090] In formula 1-1, R 11 to R14 and R 21 to R 24 Each selected from hydrogen, C1 to C 10 Alkyl, unsubstituted or substituted with C1 to C 10 Alkyl C6 to C 30 Aryl, unsubstituted or substituted with C1 to C 10 Alkyl C6 to C 30 Arylamino, unsubstituted or substituted with C1 to C 10 Alkyl C5 to C 30 Heteroaryl and unsubstituted or substituted with C1 to C 10 C3 to C 30 A group consisting of alicyclic groups, or R 11 to R 14 and R 21 to R 24 Two adjacent ones of R are connected (combined, joined or combined) to form a fused ring. 31 to R 34 Each independently selected from hydrogen, C1 to C 10 Alkyl, unsubstituted or substituted with C1 to C 10 Alkyl C6 to C 30 Aryl, unsubstituted or substituted with C1 to C 10 Alkyl C6 to C 30 Arylamino, unsubstituted or substituted with C1 to C 10 Alkyl C5 to C 30 Heteroaryl and unsubstituted or substituted with C1 to C 10 C3 to C 30 A group consisting of alicyclic groups. 51 Selected from hydrogen, C1 to C 10 Alkyl, unsubstituted or substituted with C1 to C 10 C3 to C 15 Cycloalkyl, unsubstituted or substituted with C1 to C 10 Alkyl C6 to C 30 Aryl, unsubstituted or substituted with C1 to C 10 Alkyl C5 to C 30 Heteroaryl, unsubstituted or substituted with C1 to C 10 Alkyl C6 to C 30 Arylamino, substituted or substituted with C1 to C 10 C3 to C 30 Alicyclic group, and no substituent or substituted with C1 to C 10 Alkyl C5 to C 30 A group consisting of a heterocyclic group (e.g., a heteroalicyclic group).

[0091] When R 31 、R 41 and R 51 Each is substituted with C1 to C 10 Alkyl C6 to C 30 In the case of an aryl group, the alkyl groups may be linked to each other to form a fused ring.

[0092] For example, in Formula 1-1, R 11 to R 14 、R 21 to R 24 and R 31 and R 41 Each can be independently selected from hydrogen, C1 to C 10 Alkyl, unsubstituted or substituted with C1 to C 10 Alkyl C6 to C 30 Aryl and unsubstituted or substituted with C1 to C 10 Alkyl C5 to C 30 heteroaryl; and R 51 Can be independently selected from C1 to C 10 Alkyl, unsubstituted or substituted with C1 to C 10 Alkyl C5 to C 30 Heteroaryl, unsubstituted or substituted with C1 to C 10 Alkyl C6 to C 30 Arylamino and unsubstituted or substituted with C1 to C 10 Alkyl C5 to C 30 A group consisting of heterocyclic groups.

[0093] In one exemplary embodiment, in Formula 1-1, R 11 to R 14 One and R 21 to R 24 One of them can be C1 to C 10 Alkyl, and R 11 to R 14 The rest of R 21 to R 24 The remainder of R may be hydrogen. 31 and R 41 Each may be substituted with C1 to C 10 Phenyl or substituted with C1 to C 10 Alkyl dibenzofuranyl. 51 It can be an alkyl group, a diphenylamino group, a nitrogen-containing heteroaryl group or a nitrogen-containing heterocyclic group. In this case, C1 to C 10 The alkyl group may be tert-butyl.

[0094] Unless otherwise specified, the fused ring may be C3 to C10 Alicyclic.

[0095] In Formula 1-2, X is one of NR1, CR2R3, O, S, Se, SiR4R5, and R1, R2, R3, R4, and R5 are each independently selected from hydrogen, C1 to C 10 Alkyl, C6 to C 30 Aryl, C5 to C 30 Heteroaryl, C3 to C 30 Cycloalkyl and C3 to C 30 A group consisting of alicyclic groups. 61 to R 64 are each independently selected from: hydrogen, deuterium, C1 to C2 which are unsubstituted or substituted with deuterium 10 Alkyl, unsubstituted or substituted with deuterium and C1 to C 10 At least one of the C6 to C 30 Aryl, unsubstituted or substituted with deuterium and C1 to C 10 At least one of the C6 to C 30 Arylamino, unsubstituted or substituted with deuterium and C1 to C 10 At least one of the C5 to C 30 Heteroaryl and unsubstituted or substituted with deuterium and C1 to C 10 At least one of the C3 to C 30 A group consisting of alicyclic groups, or R 61 to R 64 Two adjacent Rs are connected to form a fused ring. 71 to R 74 Each independently selected from hydrogen, deuterium, C1 to C 10 Alkyl and C3 to C 30 A group consisting of alicyclic groups. 81 Selected from the group consisting of no substituent or substituted with deuterium and C1 to C 10 At least one of the C6 to C 30 Aryl, unsubstituted or substituted with deuterium and C1 to C 10 At least one of the C5 to C 30 Heteroaryl and unsubstituted or substituted with deuterium and C1 to C 10 At least one of the C3 to C 30 Alicyclic group, or with R 61 Connect to form a fused ring. 82 Selected from the group consisting of no substituent or substituted with deuterium and C1 to C 10 At least one of the C6 to C 30 Aryl, unsubstituted or substituted with deuterium and C1 to C 10 At least one of the C5 to C 30Heteroaryl and unsubstituted or substituted with deuterium and C1 to C 10 At least one of the C3 to C 30 The group consisting of alicyclic groups, R 91 Selected from hydrogen, C1 to C 10 Alkyl, unsubstituted or substituted with C1 to C 10 C3 to C 15 Cycloalkyl, unsubstituted or substituted with C1 to C 10 Alkyl C6 to C 30 Aryl, unsubstituted or substituted with C1 to C 10 Alkyl C5 to C 30 Heteroaryl, unsubstituted or substituted with C1 to C 10 Alkyl C6 to C 30 Arylamino and unsubstituted or substituted with C1 to C 10 C3 to C 30 A group consisting of alicyclic groups.

[0096] When R 81 、R 82 and R 91 Each is substituted with C1 to C 10 Alkyl C6 to C 30 In the case of an aryl group, the alkyl groups may be linked to each other to form a fused ring.

[0097] For example, in Formula 1-2, X may be O or S. 61 to R 64 Each can be independently selected from hydrogen, deuterium, C1 to C 10 Alkyl and C6 to C 30 A group consisting of an arylamino group, or R 61 to R 64 Two adjacent R can be connected to form a fused ring. 71 to R 74 Each can be independently selected from hydrogen, deuterium and C1 to C 10 A group consisting of an alkyl group. 81 It can be selected from the group consisting of no substituent or substituted with deuterium and C1 to C 10 At least one of the C6 to C 30 Aryl and unsubstituted or substituted with deuterium and C1 to C 10 At least one of the C5 to C 30 A group consisting of heteroaryl groups, or may be combined with R 61 Connect to form a fused ring. 82 It can be selected from the group consisting of no substituent or substituted with deuterium and C1 to C 10 At least one of the C6 to C 30Aryl and unsubstituted or substituted with deuterium and C1 to C 10 At least one of the C5 to C 30 A group consisting of heteroaryl groups, and R 91 Can be selected from C1 to C 10 A group consisting of alkyl groups.

[0098] In one exemplary embodiment, in Formula 1-2, X may be O. 61 to R 64 Each may be independently selected from the group consisting of hydrogen, deuterium and diphenylamino, or R 61 to R 64 Two adjacent groups in R can be linked to form a fused ring. In this case, the diphenylamino group and the fused ring can be deuterated. 71 to R 74 Each can be independently selected from hydrogen, deuterium and C1 to C 10 A group consisting of an alkyl group. 81 and R 82 Each can be independently selected from the group consisting of unsubstituted or substituted deuterium and C1 to C 10 At least one phenyl group in the alkyl group and no substituent or substituted with deuterium and C1 to C 10 A group consisting of at least one dibenzofuranyl group in the alkyl group. 91 Can be C1 to C 10 In this case, C1 to C 10 The alkyl group may be tert-butyl.

[0099] In a further exemplary embodiment, in Formula 1-2, R 73 Can be C1 to C 10 Alkyl, and R 71 、R 72 and R 74 Each may independently be hydrogen or deuterium.

[0100] In the boron derivative in Formula 1-2, other aromatic rings and heteroaromatic rings except the benzene ring bound to the boron atom and the two nitrogen atoms may be deuterated. That is, in Formula 1-2, R 91 It doesn't have to be deuterium.

[0101] The deuterated anthracene derivative as the host 244 can be represented by Formula 2:

[0102] [Formula 2]

[0103]

[0104] In Formula 2, Ar1 and Ar2 are each independently C6 to C 30 Aryl or C5 to C 30heteroaryl, and L is a single bond or C6 to C 30 Arylene. In addition, a is an integer from 0 to 8, b, c, and d are each independently an integer from 0 to 30, and at least one of a, b, c, and d is a positive integer. (D represents a deuterium atom, and a, b, c, and d each represent the number of deuterium atoms.)

[0105] Ar1 and Ar2 may be the same or different.

[0106] In Formula 2, Ar1 and Ar2 may be selected from the group consisting of a phenyl group, a naphthyl group, a dibenzofuranyl group, a phenyl-dibenzofuranyl group, and a condensed dibenzofuranyl group, and L may be a single bond or a phenylene group.

[0107] For example, Ar1 may be selected from the group consisting of naphthyl, dibenzofuranyl, phenyl-dibenzofuranyl, and condensed dibenzofuranyl, Ar2 may be selected from the group consisting of phenyl and naphthyl, and L may be a single bond or a phenylene group.

[0108] In an exemplary embodiment, in the deuterated anthracene derivative of Formula 2, the 1-naphthalene moiety can be directly linked to the anthracene moiety, and the 2-naphthalene moiety can be directly linked to the anthracene moiety or through a phenylene linker. At least one hydrogen, preferably all hydrogens, of the anthracene derivative are substituted with deuterium.

[0109] For example, the boron derivative in Formula 1-1 or 1-2 as the dopant 242 may be one of the compounds in Formula 3.

[0110] [Formula 3]

[0111]

[0112]

[0113] For example, the anthracene derivative of Formula 2 as the host 244 may be one of the compounds of Formula 4.

[0114] [Formula 4]

[0115]

[0116] In the EML 240, the dopant 242 may be about 0.1 to 10 wt%, preferably 1 to 5 wt%, but is not limited thereto. The EML 240 may have a thickness of about 100 to 100 wt%. The thickness is preferably 100 to , but not limited to this.

[0117] In the OLED D of the present disclosure, since the EML 240 includes the dopant 242 that is a boron derivative and the host 244 that is a deuterated anthracene derivative, the luminous efficiency and lifespan of the OLED D and the organic light emitting display device 100 are improved.

[0118] In addition, when the EML 240 includes the boron derivative as the dopant 242 having the asymmetric structure as shown in Formula 1-2, the luminous efficiency and lifespan of the OLED D and the organic light emitting display device 100 are further improved.

[0119] Furthermore, when the EML 240 includes a boron derivative as the dopant 242 in which aromatic and heteroaromatic rings other than the benzene ring bound to the boron atom and two nitrogen atoms are partially or completely deuterated, the luminous efficiency and lifespan of the OLED D and the organic light-emitting display device 100 are further improved.

[0120] Furthermore, when the anthracene derivative as the host 244 includes two naphthalene moieties connected to an anthracene moiety and is partially or fully deuterated, the luminous efficiency and lifespan of the OLED D and the organic light-emitting display device 100 including the anthracene derivative are further improved.

[0121] [Synthesis of dopant]

[0122] 1. Synthesis of Compound 1-1

[0123] (1) Compound I1-1c

[0124] [Reaction formula 1-1]

[0125]

[0126] Compound I1-1a (69.2 g, 98 mmol), compound I1-1b (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 flask and refluxed for 5 hours. After the reaction was completed, the mixture was filtered and the residual solution was concentrated. The mixture was separated by column chromatography to obtain compound I1-1c (58.1 g). (Yield 84%).

[0127] (2) Compound 1-1

[0128] [Reaction formula 1-2]

[0129]

[0130] Compound I1-1c (11.9 g, 12.5 mmol) and tert-butylbenzene (60 ml) were added to a 500 mL flask. At a temperature of -78 ° C, n-butyllithium (45 mL, 37.5 mmol) in heptane was added dropwise to the mixture, and the mixture was stirred at a temperature of 60 ° C for 3 hours. Heptane was removed by blowing nitrogen at 60 ° C. Boron tribromide (6.3 g, 25 mmol) was added dropwise at -78 ° C. The mixture was stirred at room temperature for 1 hour, and N, N-diisopropylethylamine (3.2 g, 25 mmol) was added dropwise at 0 ° C. The mixture was stirred at 120 ° C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added and stirred at room temperature. After extraction with ethyl acetate, the organic layer was concentrated. The mixture was separated by column chromatography to obtain compound I-1 (2.3 g). (Yield 20%)

[0131] 2. Synthesis of Compounds 1-4

[0132] (1) Compound I1-4c

[0133] [Reaction formula 2-1]

[0134]

[0135] Compound I1-4a (43.1 g, 98 mmol), compound I1-4b (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 flask and refluxed for 5 hours. After the reaction was completed, the mixture was filtered and the residual solution was concentrated. The mixture was separated by column chromatography to obtain compound I1-4c (57.1 g). (Yield 85%).

[0136] (2) Compounds 1-4

[0137] [Reaction formula 2-2]

[0138]

[0139] Compound I1-4c (8.6g, 12.5mmol) and tert-butylbenzene (60ml) are added to a 500mL flask. At a temperature of -78°C, n-butyllithium (45mL, 37.5mmol) in heptane is added dropwise to the mixture, and the mixture is stirred at a temperature of 60°C for 3 hours. Heptane is removed by blowing nitrogen at 60°C. Boron tribromide (6.3g, 25mmol) is added dropwise at -78°C. The mixture is stirred at room temperature for 1 hour, and N,N-diisopropylethylamine (3.2g, 25mmol) is added dropwise at 0°C. The mixture is stirred at 120°C for 2 hours. After the reaction is completed, sodium acetate aqueous solution is added and stirred at room temperature. After extraction with ethyl acetate, the organic layer is concentrated. The mixture is separated by column chromatography to obtain compound I-4 (1.9g). (Yield 23%).

[0140] 3. Synthesis of Compounds 1-6

[0141] (1) Compound I1-6c

[0142] [Reaction formula 3-1]

[0143]

[0144] Compound I1-6a (58.9 g, 98 mmol), compound I1-6b (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 flask and refluxed for 5 hours. After the reaction was completed, the mixture was filtered and the residual solution was concentrated. The mixture was separated by column chromatography to obtain compound I1-6c (59.7 g). (Yield 75%).

[0145] (2) Compounds 1-6

[0146] [Reaction formula 3-2]

[0147]

[0148] Compound I1-6c (10.1g, 12.5mmol) and tert-butylbenzene (60ml) are added to a 500mL flask. At a temperature of -78°C, n-butyllithium (45mL, 37.5mmol) in heptane is added dropwise to the mixture, and the mixture is stirred at a temperature of 60°C for 3 hours. Heptane is removed by blowing nitrogen at 60°C. Boron tribromide (6.3g, 25mmol) is added dropwise at -78°C. The mixture is stirred at room temperature for 1 hour, and N,N-diisopropylethylamine (3.2g, 25mmol) is added dropwise at 0°C. The mixture is stirred at 120°C for 2 hours. After the reaction is completed, sodium acetate aqueous solution is added and stirred at room temperature. After extraction with ethyl acetate, the organic layer is concentrated. The mixture is separated by column chromatography to obtain compound I-6 (1.9g). (Yield 21%)

[0149] 4. Synthesis of Compounds 1-8

[0150] (1) Compound I1-8c

[0151] [Reaction formula 4-1]

[0152]

[0153] Compound I1-8a (33.0 g, 98 mmol), compound I1-8b (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 flask and refluxed for 5 hours. After the reaction was completed, the mixture was filtered and the residual solution was concentrated. The mixture was separated by column chromatography to obtain compound I1-8c (54.1 g). (Yield 72%).

[0154] (2) Compounds 1-8

[0155] [Reaction Formula 4-2]

[0156]

[0157] Compound I1-8c (9.6g, 12.5mmol) and tert-butylbenzene (60ml) are added to a 500mL flask. At a temperature of -78°C, n-butyllithium (45mL, 37.5mmol) in heptane is added dropwise to the mixture, and the mixture is stirred at a temperature of 60°C for 3 hours. Heptane is removed by blowing nitrogen at 60°C. Boron tribromide (6.3g, 25mmol) is added dropwise at -78°C. The mixture is stirred at room temperature for 1 hour, and N,N-diisopropylethylamine (3.2g, 25mmol) is added dropwise at 0°C. The mixture is stirred at 120°C for 2 hours. After the reaction is completed, sodium acetate aqueous solution is added and stirred at room temperature. After extraction with ethyl acetate, the organic layer is concentrated. The mixture is separated by column chromatography to obtain compound I-8 (2.0g). (Yield 21%).

[0158] 5. Synthesis of Compounds 1-11

[0159] (1) Compound I1-11c

[0160] [Reaction Formula 5-1]

[0161]

[0162] Compound II-11a (28.4 g, 98 mmol), compound II-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 flask and refluxed for 5 hours. After the reaction was complete, the mixture was filtered and the residual solution was concentrated. The mixture was separated by column chromatography to obtain compound II-11c (39.9 g). (Yield 52%).

[0163] (2) Compounds 1-11

[0164] [Reaction Formula 5-2]

[0165]

[0166] Compound I1-11c (9.8g, 12.5mmol) and tert-butylbenzene (60ml) are added to a 500mL flask. At a temperature of -78°C, n-butyllithium (45mL, 37.5mmol) in heptane is added dropwise to the mixture, and the mixture is stirred at a temperature of 60°C for 3 hours. Heptane is removed by blowing nitrogen at 60°C. Boron tribromide (6.3g, 25mmol) is added dropwise at -78°C. The mixture is stirred at room temperature for 1 hour, and N,N-diisopropylethylamine (3.2g, 25mmol) is added dropwise at 0°C. The mixture is stirred at 120°C for 2 hours. After the reaction is completed, sodium acetate aqueous solution is added and stirred at room temperature. After extraction with ethyl acetate, the organic layer is concentrated. The mixture is separated by column chromatography to obtain compound I-11 (1.4g). (Yield 15%)

[0167] 6. Synthesis of Compounds 1-12

[0168] (1) Compound I1-12c

[0169] [Reaction formula 6-1]

[0170]

[0171] Compound II-12a (28.0 g, 98 mmol), compound II-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 flask and refluxed for 5 hours. After the reaction was complete, the mixture was filtered and the residual solution was concentrated. The mixture was separated by column chromatography to obtain compound II-12c (44.1 g). (Yield 58%).

[0172] (2) Compounds 1-12

[0173] [Reaction formula 6-2]

[0174]

[0175] Compound I1-12c (9.7g, 12.5mmol) and tert-butylbenzene (60ml) are added to a 500mL flask. At a temperature of -78°C, n-butyllithium (45mL, 37.5mmol) in heptane is added dropwise to the mixture, and the mixture is stirred at a temperature of 60°C for 3 hours. Heptane is removed by blowing nitrogen at 60°C. Boron tribromide (6.3g, 25mmol) is added dropwise at -78°C. The mixture is stirred at room temperature for 1 hour, and N,N-diisopropylethylamine (3.2g, 25mmol) is added dropwise at 0°C. The mixture is stirred at 120°C for 2 hours. After the reaction is completed, sodium acetate aqueous solution is added and stirred at room temperature. After extraction with ethyl acetate, the organic layer is concentrated. The mixture is separated by column chromatography to obtain compound I-12 (1.7g). (Yield 18%)

[0176] 7. Synthesis of Compounds 1-13

[0177] (1) Compound I1-13c

[0178] [Reaction Formula 7-1]

[0179]

[0180] Compound II-13a (34.8 g, 98 mmol), compound II-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 flask and refluxed for 5 hours. After the reaction was complete, the mixture was filtered and the residual solution was concentrated. The mixture was separated by column chromatography to obtain compound II-13c (41.3 g). (Yield 53%).

[0181] (2) Compounds 1-13

[0182] [Reaction Formula 7-2]

[0183]

[0184] Compound I1-13c (9.9 g, 12.5 mmol) and tert-butylbenzene (60 ml) were added to a 500 mL flask. At a temperature of -78 ° C, n-butyllithium (45 mL, 37.5 mmol) in heptane was added dropwise to the mixture, and the mixture was stirred at a temperature of 60 ° C for 3 hours. Heptane was removed by blowing nitrogen at 60 ° C. Boron tribromide (6.3 g, 25 mmol) was added dropwise at -78 ° C. The mixture was stirred at room temperature for 1 hour, and N, N-diisopropylethylamine (3.2 g, 25 mmol) was added dropwise at 0 ° C. The mixture was stirred at 120 ° C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added and stirred at room temperature. After extraction with ethyl acetate, the organic layer was concentrated. The mixture was separated by column chromatography to obtain compound I-13 (1.4 g). (Yield 15%)

[0185] 8. Synthesis of Compounds 1-17

[0186] (1) Compound I1-17c

[0187] [Reaction formula 8-1]

[0188]

[0189] Compound II-17a (33.4 g, 98 mmol), compound II-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 flask and refluxed for 5 hours. After the reaction was completed, the mixture was filtered and the residual solution was concentrated. The mixture was separated by column chromatography to obtain compound II-17c (47.1 g). (Yield 62%).

[0190] (2) Compounds 1-17

[0191] [Reaction formula 8-2]

[0192]

[0193] Compound I1-18c (9.7g, 12.5mmol) and tert-butylbenzene (60ml) are added to a 500mL flask. At a temperature of -78°C, n-butyllithium (45mL, 37.5mmol) in heptane is added dropwise to the mixture, and the mixture is stirred at a temperature of 60°C for 3 hours. Heptane is removed by blowing nitrogen at 60°C. Boron tribromide (6.3g, 25mmol) is added dropwise at -78°C. The mixture is stirred at room temperature for 1 hour, and N,N-diisopropylethylamine (3.2g, 25mmol) is added dropwise at 0°C. The mixture is stirred at 120°C for 2 hours. After the reaction is completed, sodium acetate aqueous solution is added and stirred at room temperature. After extraction with ethyl acetate, the organic layer is concentrated. The mixture is separated by column chromatography to obtain compound I-17 (1.6g). (Yield 17%)

[0194] [Synthesis of the subject]

[0195] 1. Synthesis of Compound 2-1

[0196] [Reaction formula 9]

[0197]

[0198] Compound I2-1a (2.0 g, 5.2 mmol), compound I2-1b (1.5 g, 5.7 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.24 g, 0.26 mmol) and toluene (50 mL) were added to a 250 mL reactor in a drying oven. After the reactor was taken out of the drying oven, anhydrous sodium carbonate (2 M, 20 mL) was added to the mixture. The reactants were stirred and heated at 90 ° C overnight. The reaction was monitored by high performance liquid chromatography (HPLC). After the mixture was cooled to room temperature, the organic layer was separated from the mixture. 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 using alumina, precipitated with hexane and subjected to column chromatography on silica gel to obtain compound 2-1 (2.3 g) as a white powder. (Yield 86%)

[0199] 2. Synthesis of Compound 2-2

[0200] [Reaction formula 10]

[0201]

[0202] Compound I2-2a (2.0 g, 5.2 mmol), compound I2-2b (1.5 g, 5.7 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.24 g, 0.26 mmol) and toluene (50 mL) were added to a 250 mL reactor in a drying oven. After the reactor was taken out of the drying oven, anhydrous sodium carbonate (2 M, 20 mL) was added to the mixture. The reactants were stirred and heated at 90 ° C overnight. The reaction was monitored by high performance liquid chromatography (HPLC). After the mixture was cooled to room temperature, the organic layer was separated from the mixture. 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 using alumina, precipitated with hexane and subjected to column chromatography on silica gel to obtain compound 2-2 (2.0 g) as a white powder. (Yield 89%)

[0203] 3. Synthesis of Compound 2-3

[0204] [Reaction formula 11]

[0205]

[0206] Compound I2-3a (2.0 g, 6.0 mmol), compound I2-3b (1.9 g, 6.6 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.3 g, 0.3 mmol) and toluene (50 mL) were added to a 250 mL reactor in a drying oven. After the reactor was taken out of the drying oven, anhydrous sodium carbonate (2 M, 20 mL) was added to the mixture. The reactants were stirred and heated at 90 ° C overnight. The reaction was monitored by high performance liquid chromatography (HPLC). After the mixture was cooled to room temperature, the organic layer was separated from the mixture. 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 using alumina, precipitated with hexane and subjected to column chromatography on silica gel to obtain compound 2-3 (2.0 g) as a white powder. (Yield 79%)

[0207] 4. Synthesis of Compounds 2-4

[0208] [Reaction formula 12]

[0209]

[0210] Compound I2-4a (2.0 g, 6.0 mmol), compound I2-4b (2.4 g, 6.6 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.3 g, 0.3 mmol) and toluene (50 mL) were added to a 250 mL reactor in a drying oven. After the reactor was taken out of the drying oven, anhydrous sodium carbonate (2 M, 20 mL) was added to the mixture. The reactants were stirred and heated at 90 ° C overnight. The reaction was monitored by high performance liquid chromatography (HPLC). After the mixture was cooled to room temperature, the organic layer was separated from the mixture. 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 using alumina, precipitated with hexane and subjected to column chromatography on silica gel to obtain compound 2-4 (2.0 g) as a white powder. (Yield 67%)

[0211] 5. Synthesis of Compounds 2-5

[0212] [Reaction formula 13]

[0213]

[0214] Compound I2-5a (2.0 g, 5.2 mmol), compound I2-5b (2.0 g, 5.7 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.24 g, 0.26 mmol) and toluene (50 mL) were added to a 250 mL reactor in a drying oven. After the reactor was taken out of the drying oven, anhydrous sodium carbonate (2 M, 20 mL) was added to the mixture. The reactants were stirred and heated at 90 ° C overnight. The reaction was monitored by high performance liquid chromatography (HPLC). After the mixture was cooled to room temperature, the organic layer was separated from the mixture. 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 using alumina, precipitated with hexane and subjected to column chromatography on silica gel to obtain compound 2-5 (2.0 g) as a white powder. (Yield 81%)

[0215] 6. Synthesis of Compounds 2-6

[0216] [Reaction formula 14]

[0217]

[0218] Compound I2-6a (2.0 g, 5.2 mmol), compound I2-6b (2.0 g, 5.7 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.24 g, 0.26 mmol) and toluene (50 mL) were added to a 250 mL reactor in a drying oven. After the reactor was taken out of the drying oven, anhydrous sodium carbonate (2 M, 20 mL) was added to the mixture. The reactants were stirred and heated at 90 ° C overnight. The reaction was monitored by high performance liquid chromatography (HPLC). After the mixture was cooled to room temperature, the organic layer was separated from the mixture. 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 using alumina, precipitated with hexane and subjected to column chromatography using silica gel to obtain compound 2-6 (2.0 g) as a white powder. (Yield 81%)

[0219] 7. Synthesis of Compounds 2-7

[0220] [Reaction formula 15]

[0221]

[0222] Under nitrogen conditions, aluminum chloride (0.5 g, 3.6 mmol) was added to a perdeuterobenzene solution (100 mL) in which compound 2-1 (5.0 g, 9.9 mmol) was dissolved. The product of the mixture was stirred at room temperature for 6 hours, and D2O (50 mL) was added. After separation of the organic layer, the aqueous layer was washed with dichloromethane (30 mL). The obtained organic layer was dried over magnesium sulfate and volatiles were removed by rotary evaporation. Thereafter, the crude product was purified by column chromatography to obtain compound 2-7 (4.5 g) as a white powder. (Yield 85%)

[0223] 8. Synthesis of Compounds 2-8

[0224] [Reaction formula 16]

[0225]

[0226] Under nitrogen conditions, aluminum chloride (0.9 g, 4.3 mmol) was added to a perdeuterated benzene solution (120 mL) in which compound 2-2 (5.0 g, 11.6 mmol) was dissolved. The product of the mixture was stirred at room temperature for 6 hours, and D2O (70 mL) was added. After separation of the organic layer, the aqueous layer was washed with dichloromethane (50 mL). The obtained organic layer was dried over magnesium sulfate and volatiles were removed by rotary evaporation. Thereafter, the crude product was purified by column chromatography to obtain compound 2-8 (4.0 g) as a white powder. (Yield 76%)

[0227] 9. Synthesis of Compound 2-9

[0228] [Reaction 17]

[0229]

[0230] Under nitrogen conditions, aluminum chloride (0.9 g, 4.3 mmol) was added to a perdeuterated benzene solution (120 mL) in which compound 2-3 (5.0 g, 11.9 mmol) was dissolved. The product of the mixture was stirred at room temperature for 6 hours, and D2O (70 mL) was added. After separation of the organic layer, the aqueous layer was washed with dichloromethane (50 mL). The obtained organic layer was dried over magnesium sulfate and volatiles were removed by rotary evaporation. Thereafter, the crude product was purified by column chromatography to obtain compound 2-9 (3.0 g) as a white powder. (Yield 57%)

[0231] 10. Synthesis of Compound 2-10

[0232] [Reaction formula 18]

[0233]

[0234] Under nitrogen conditions, aluminum chloride (0.9 g, 4.3 mmol) was added to a perdeuterated benzene solution (120 mL) in which compound 2-4 (5.0 g, 10.1 mmol) was dissolved. The product of the mixture was stirred at room temperature for 6 hours, and D2O (70 mL) was added. After separation of the organic layer, the aqueous layer was washed with dichloromethane (50 mL). The resulting organic layer was dried over magnesium sulfate and volatiles were removed by rotary evaporation. Thereafter, the crude product was purified by column chromatography to obtain compound 2-10 (3.5 g) as a white powder. (Yield 67%)

[0235] 11. Synthesis of Compound 2-11

[0236] [Reaction formula 19]

[0237]

[0238] Under nitrogen conditions, aluminum chloride (0.9 g, 4.3 mmol) was added to a perdeuterated benzene solution (120 mL) in which compound 2-5 (5.0 g, 10.6 mmol) was dissolved. The product of the mixture was stirred at room temperature for 6 hours, and then D2O (70 mL) was added. After separation of the organic layer, the aqueous layer was washed with dichloromethane (50 mL). The obtained organic layer was dried over magnesium sulfate and volatiles were removed by rotary evaporation. Thereafter, the crude product was purified by column chromatography to obtain compound 2-11 (4.0 g) as a white powder. (Yield 77%)

[0239] 12. Synthesis of Compound 2-12

[0240] [Reaction formula 20]

[0241]

[0242] Under nitrogen conditions, aluminum chloride (0.9 g, 4.3 mmol) was added to a perdeuterated benzene solution (120 mL) in which compound 2-6 (5.0 g, 10.6 mmol) was dissolved. The product of the mixture was stirred at room temperature for 6 hours, and then D2O (70 mL) was added. After separation of the organic layer, the aqueous layer was washed with dichloromethane (50 mL). The obtained organic layer was dried over magnesium sulfate and volatiles were removed by rotary evaporation. Thereafter, the crude product was purified by column chromatography to obtain compound 2-12 (4.3 g) as a white powder. (Yield 82%)

[0243] The EBL 230 includes an amine derivative as an electron blocking material 232. The electron blocking material 232 may be represented by Formula 5:

[0244] [Formula 5]

[0245]

[0246] In Formula 5, R1, R2, and R4 are each independently selected from the group consisting of a monocyclic aryl group or a polycyclic aryl group, R3 is a monocyclic arylene group or a polycyclic arylene group, and at least one of R1, R2, R3, and R4 is polycyclic. For example, at least two of R1, R2, R3, and R4 may be polycyclic. The monocyclic aryl group may be phenyl, and the polycyclic aryl group may be C 10 to C 13 Fused aryl. Monocyclic arylene can be phenylene, polycyclic arylene can be C 10 to C 13 Fused arylene groups. The polycyclic aryl group may be an aryl group fused with at least two phenyl groups, and may include phenyl, anthracenyl, phenanthrenyl, and pyrenyl. The polycyclic arylene group may be an arylene group fused with at least two phenylene groups, and may include phenylene, anthracenyl, phenanthrenyl, and pyrenyl.

[0247] The electron blocking material of Formula 5 may be one of the following compounds of Formula 6:

[0248] [Formula 6]

[0249]

[0250]

[0251] The HBL 250 includes a hole blocking material 252 .

[0252] For example, the hole blocking material 252 may be an azine derivative represented by Formula 7:

[0253] [Formula 7]

[0254]

[0255] In Formula 7, Y1 to Y5 are each independently CR1 or N, and one to three of Y1 to Y5 are N. R1 is independently hydrogen or C6 to C 30 Aryl. L is C6 to C 30 Arylene, and R2 is C6 to C 50 Aryl or C5 to C 50 Heteroaryl. R3 is C1 to C 10 Alkyl, or two adjacent R3 are connected to each other to form a condensed ring. In addition, a is 0 or 1, b is 1 or 2, and c is an integer from 0 to 4.

[0256] The hole blocking material 252 of Formula 7 may be one of the following compounds of Formula 8:

[0257] [Formula 8]

[0258]

[0259]

[0260] Alternatively, the hole blocking material 252 of the HBL 250 may be a benzimidazole derivative represented by Formula 9:

[0261] [Formula 9]

[0262]

[0263] In formula 9, Ar is C 10 to C 30 Arylene, R 81 is unsubstituted or substituted with C1 to C 10 Alkyl C6 to C 30 The aryl group may be unsubstituted or substituted with C1 to C 10 Alkyl C5 to C 30 heteroaryl, and R 82 and R 83 are each independently hydrogen, C1 to C 10 Alkyl or C6 to C 30 Aryl.

[0264] For example, Ar can be naphthylene or anthracenylene, R 81 It can be benzimidazolyl or phenyl. 82 can be methyl, ethyl or phenyl, and R 83 It may be hydrogen, methyl or phenyl.

[0265] The hole blocking material 252 of Formula 9 may be one of the following compounds of Formula 10:

[0266] [Equation 10]

[0267]

[0268] The hole blocking material 252 of the HBL 250 may include one of the compound of Formula 7 and the compound of Formula 9.

[0269] In this case, the thickness of the EML 240 may be greater than each of the EBL 230 and the HBL 250, and may be smaller than the HTL 220. For example, the thickness of the EML 240 may be about 150 to 2000 Å. The thickness of each of the EBL 230 and the HBL 250 may be from about 50 to The thickness of HTL 220 may be about 900 to The EBL 230 and the HBL 250 may have the same thickness.

[0270] Alternatively, the hole blocking material 252 of the HBL 250 may include both the compound of Formula 7 and the compound of Formula 9. For example, in the HBL 250, the compound of Formula 7 and the compound of Formula 9 may have the same weight %.

[0271] In this case, the thickness of the EML 240 may be greater than that of the EBL 230 and may be smaller than that of the HBL 250. In addition, the thickness of the HBL 250 may be smaller than that of the HTL 220. For example, the thickness of the EML 240 may be about 200 to 300 Å. The thickness of the EBL 230 may be from about 50 to The thickness of HBL 250 may be from about 250 to , and the thickness of the HTL 220 may be about 800 to .

[0272] The compound in Formula 7 and / or 9, i.e., the hole blocking material 252, has excellent hole blocking properties and excellent electron transport properties. Therefore, the HBL 250 can serve as a hole blocking layer as well as an electron transport layer (ETL). In this case, the HBL 250 can directly contact the EIL 260 without the ETL. Alternatively, the HBL 250 can directly contact the second electrode 164 without the ETL and the EIL 260.

[0273] In the OLED D, the EML 240 includes a dopant 242 that is a boron derivative and a host 244 that is a deuterated anthracene derivative. As a result, the OLED D and the organic light emitting display device 100 have advantages in terms of luminous efficiency and lifespan.

[0274] In addition, when the boron derivative as the dopant 242 has an asymmetric structure as shown in Formula 1-2, the luminous efficiency and lifespan of the OLED D and the organic light emitting display device 100 are further improved.

[0275] Furthermore, when a boron derivative in which aromatic and heteroaromatic rings other than a benzene ring bound to a boron atom and two nitrogen atoms are partially or completely deuterated is included as the dopant 242 , the luminous efficiency and lifespan of the OLED D and the organic light-emitting display device 100 are further improved.

[0276] Furthermore, when the anthracene derivative as the host 244 includes two naphthalene moieties connected to an anthracene moiety and is partially or fully deuterated, the luminous efficiency and lifespan of the OLED D and the organic light-emitting display device 100 including the anthracene derivative are further improved.

[0277] In addition, since the EBL 230 includes the compound of Formula 5 as the electron blocking material 232 and the HBL 250 includes at least one of the compounds of Formula 7 and Formula 9 as the hole blocking material 252 , the luminous efficiency and lifespan of the OLED D and the organic light emitting display device 100 are further improved.

[0278] [Organic Light Emitting Diode]

[0279] Anode (ITO, 0.5 mm), HIL (Formula 12 (97 wt%) and Formula 13 (3 wt%)) were deposited in sequence. ), HTL (Formula 12, ), EBL , EML (host (98 wt%) and dopant (2 wt%), ), HBL , EIL (Formula 14 (98 wt%) and Li (2 wt%), ) and cathode (Al, ). An encapsulation film is formed by using a UV-curable epoxy resin and a moisture absorbent to form an OLED.

[0280] [Equation 12]

[0281]

[0282] [Equation 13]

[0283]

[0284] [Equation 14]

[0285]

[0286] 1. Comparative Example

[0287] (1) Comparative Example 1 (Ref 1)

[0288] The compound "Ref" in Formula 15 is used to form the EBL, the compound 1-6 in Formula 3 is used as a dopant, and the compound 2-1 is used as a host to form the EML. The compound "Ref" in Formula 16 is used to form the HBL.

[0289] (2) Comparative Example 2 (Ref2)

[0290] The compound "Ref" in Formula 15 is used to form the EBL, and the compounds 1-6 in Formula 3 are used as dopants and the compounds 2-3 are used as hosts to form the EML. The compound "Ref" in Formula 16 is used to form the HBL.

[0291] (3) Comparative Example 3 (Ref3)

[0292] The compound "Ref" in Formula 15 is used to form the EBL, the compound 1-8 in Formula 3 is used as a dopant, and the compound 2-1 is used as a host to form the EML. The compound "Ref" in Formula 16 is used to form the HBL.

[0293] (4) Comparative Example 4 (Ref4)

[0294] The compound "Ref" in Formula 15 is used to form the EBL, the compounds 1-8 in Formula 3 are used as dopants, and the compounds 2-3 are used as hosts to form the EML. The compound "Ref" in Formula 16 is used to form the HBL.

[0295] (5) Comparative Example 5 (Ref5)

[0296] The compound "Ref" in Formula 15 is used to form the EBL, the compound 1-11 in Formula 3 is used as a dopant, and the compound 2-1 is used as a host to form the EML. The compound "Ref" in Formula 16 is used to form the HBL.

[0297] (6) Comparative Example 6 (Ref6)

[0298] The compound "Ref" in Formula 15 is used to form the EBL, and the compounds 1-11 in Formula 3 are used as dopants and the compounds 2-3 are used as hosts to form the EML. The compound "Ref" in Formula 16 is used to form the HBL.

[0299] (7) Comparative Example 7 (Ref7)

[0300] The compound "Ref" in Formula 15 is used to form the EBL, the compound 1-13 in Formula 3 is used as a dopant, and the compound 2-1 is used as a host to form the EML. The compound "Ref" in Formula 16 is used to form the HBL.

[0301] (8) Comparative Example 8 (Ref8)

[0302] The compound "Ref" in Formula 15 is used to form the EBL, and the compounds 1-13 in Formula 3 are used as dopants and the compounds 2-3 are used as hosts to form the EML. The compound "Ref" in Formula 16 is used to form the HBL.

[0303] 2. Examples

[0304] (1) Examples 1 to 3 (Ex1 to Ex3)

[0305] Compound "Ref" in Formula 15 is used to form the EBL, compounds 1-6 in Formula 3 serve as dopants, and compounds 2-7 in Formula 4 serve as hosts to form the EML. Compound "Ref" in Formula 16, compound E1 in Formula 8 ("HBL-1-1"), and compound F1 in Formula 10 ("HBL-2-1") are each used to form the HBL.

[0306] (2) Examples 4 to 6 (Ex4 to Ex6)

[0307] Compound H-3 ("EBL-1") in Formula 6 is used to form the EBL, compounds 1-6 in Formula 3 serve as dopants, and compounds 2-7 in Formula 4 serve as hosts to form the EML. Compound "Ref" in Formula 16, compound E1 ("HBL-1-1") in Formula 8, and compound F1 ("HBL-2-1") in Formula 10 are each used to form the HBL.

[0308] (3) Examples 7 to 9 (Ex7 to Ex9)

[0309] Compound H-9 ("EBL-2") in Formula 6 is used to form the EBL, compounds 1-6 in Formula 3 serve as dopants, and compounds 2-7 in Formula 4 serve as hosts to form the EML. Compound "Ref" in Formula 16, compound E1 ("HBL-1-1") in Formula 8, and compound F1 ("HBL-2-1") in Formula 10 are each used to form the HBL.

[0310] (4) Examples 10 to 12 (Ex10 to Ex12)

[0311] Compound "Ref" in Formula 15 is used to form the EBL, compounds 1-6 in Formula 3 serve as dopants, and compounds 2-9 in Formula 4 serve as hosts to form the EML. Compound "Ref" in Formula 16, compound E1 in Formula 8 ("HBL-1-1"), and compound F1 in Formula 10 ("HBL-2-1") are each used to form the HBL.

[0312] (5) Examples 13 to 15 (Ex13 to Ex15)

[0313] Compound H-3 ("EBL-1") in Formula 6 is used to form the EBL, compounds 1-6 in Formula 3 serve as dopants, and compounds 2-9 in Formula 4 serve as hosts to form the EML. Compound "Ref" in Formula 16, compound E1 ("HBL-1-1") in Formula 8, and compound F1 ("HBL-2-1") in Formula 10 are each used to form the HBL.

[0314] (6) Examples 16 to 18 (Ex16 to Ex18)

[0315] Compound H-9 ("EBL-2") in Formula 6 is used to form the EBL, Compound 1-6 in Formula 3 serves as a dopant, and Compound 2-9 in Formula 4 serves as a host to form the EML. Compound "Ref" in Formula 16, Compound E1 ("HBL-1-1") in Formula 8, and Compound F1 ("HBL-2-1") in Formula 10 are each used to form the HBL.

[0316] (7) Examples 19 to 21 (Ex19 to Ex21)

[0317] Compound "Ref" in Formula 15 is used to form the EBL, compounds 1-8 in Formula 3 serve as dopants, and compounds 2-7 in Formula 4 serve as hosts to form the EML. Compound "Ref" in Formula 16, compound E1 in Formula 8 ("HBL-1-1"), and compound F1 in Formula 10 ("HBL-2-1") are each used to form the HBL.

[0318] (8) Examples 22 to 24 (Ex22 to Ex24)

[0319] Compound H-3 ("EBL-1") in Formula 6 is used to form the EBL, compounds 1-8 in Formula 3 serve as dopants, and compounds 2-7 in Formula 4 serve as hosts to form the EML. Compound "Ref" in Formula 16, compound E1 ("HBL-1-1") in Formula 8, and compound F1 ("HBL-2-1") in Formula 10 are each used to form the HBL.

[0320] (9) Examples 25 to 27 (Ex25 to Ex27)

[0321] Compound H-9 ("EBL-2") in Formula 6 is used to form the EBL, Compounds 1-8 in Formula 3 serve as dopants, and Compounds 2-7 in Formula 4 serve as hosts to form the EML. Compound "Ref" in Formula 16, Compound E1 ("HBL-1-1") in Formula 8, and Compound F1 ("HBL-2-1") in Formula 10 are each used to form the HBL.

[0322] (10) Examples 28 to 30 (Ex28 to Ex30)

[0323] Compound "Ref" in Formula 15 is used to form the EBL, compounds 1-8 in Formula 3 serve as dopants, and compounds 2-9 in Formula 4 serve as hosts to form the EML. Compound "Ref" in Formula 16, compound E1 in Formula 8 ("HBL-1-1"), and compound F1 in Formula 10 ("HBL-2-1") are each used to form the HBL.

[0324] (11) Examples 31 to 33 (Ex31 to Ex33)

[0325] Compound H-3 ("EBL-1") in Formula 6 is used to form the EBL, compounds 1-8 in Formula 3 serve as dopants, and compounds 2-9 in Formula 4 serve as hosts to form the EML. Compound "Ref" in Formula 16, compound E1 ("HBL-1-1") in Formula 8, and compound F1 ("HBL-2-1") in Formula 10 are each used to form the HBL.

[0326] (12) Examples 34 to 36 (Ex34 to Ex36)

[0327] Compound H-9 ("EBL-2") in Formula 6 is used to form the EBL, Compound 1-8 in Formula 3 serves as a dopant, and Compound 2-9 in Formula 4 serves as a host to form the EML. Compound "Ref" in Formula 16, Compound E1 ("HBL-1-1") in Formula 8, and Compound F1 ("HBL-2-1") in Formula 10 are each used to form the HBL.

[0328] (13) Examples 37 to 39 (Ex37 to Ex39)

[0329] Compound "Ref" in Formula 15 is used to form the EBL, compounds 1-11 in Formula 3 serve as dopants, and compounds 2-7 in Formula 4 serve as hosts to form the EML. Compound "Ref" in Formula 16, compound E1 in Formula 8 ("HBL-1-1"), and compound F1 in Formula 10 ("HBL-2-1") are each used to form the HBL.

[0330] (14) Examples 40 to 42 (Ex40 to Ex42)

[0331] Compound H-3 ("EBL-1") in Formula 6 is used to form the EBL, Compound 1-11 in Formula 3 serves as a dopant, and Compound 2-7 in Formula 4 serves as a host to form the EML. Compound "Ref" in Formula 16, Compound E1 ("HBL-1-1") in Formula 8, and Compound F1 ("HBL-2-1") in Formula 10 are each used to form the HBL.

[0332] (15) Examples 43 to 45 (Ex43 to Ex45)

[0333] Compound H-9 ("EBL-2") in Formula 6 is used to form the EBL, Compound 1-11 in Formula 3 serves as a dopant, and Compound 2-7 in Formula 4 serves as a host to form the EML. Compound "Ref" in Formula 16, Compound E1 ("HBL-1-1") in Formula 8, and Compound F1 ("HBL-2-1") in Formula 10 are each used to form the HBL.

[0334] (16) Examples 46 to 48 (Ex46 to Ex48)

[0335] Compound "Ref" in Formula 15 is used to form the EBL, compounds 1-11 in Formula 3 serve as dopants, and compounds 2-9 in Formula 4 serve as hosts to form the EML. Compound "Ref" in Formula 16, compound E1 in Formula 8 ("HBL-1-1"), and compound F1 in Formula 10 ("HBL-2-1") are each used to form the HBL.

[0336] (17) Examples 49 to 51 (Ex49 to Ex51)

[0337] Compound H-3 ("EBL-1") in Formula 6 is used to form the EBL, Compound 1-11 in Formula 3 serves as a dopant, and Compound 2-9 in Formula 4 serves as a host to form the EML. Compound "Ref" in Formula 16, Compound E1 ("HBL-1-1") in Formula 8, and Compound F1 ("HBL-2-1") in Formula 10 are each used to form the HBL.

[0338] (18) Examples 52 to 54 (Ex52 to Ex54)

[0339] Compound H-9 ("EBL-2") in Formula 6 is used to form the EBL, Compound 1-11 in Formula 3 serves as a dopant, and Compound 2-9 in Formula 4 serves as a host to form the EML. Compound "Ref" in Formula 16, Compound E1 ("HBL-1-1") in Formula 8, and Compound F1 ("HBL-2-1") in Formula 10 are each used to form the HBL.

[0340] (19) Examples 55 to 57 (Ex55 to Ex57)

[0341] Compound "Ref" in Formula 15 is used to form the EBL, compounds 1-13 in Formula 3 serve as dopants, and compounds 2-7 in Formula 4 serve as hosts to form the EML. Compound "Ref" in Formula 16, compound E1 in Formula 8 ("HBL-1-1"), and compound F1 in Formula 10 ("HBL-2-1") are each used to form the HBL.

[0342] (20) Examples 58 to 60 (Ex58 to Ex60)

[0343] Compound H-3 ("EBL-1") in Formula 6 is used to form the EBL, Compound 1-13 in Formula 3 serves as a dopant, and Compound 2-7 in Formula 4 serves as a host to form the EML. Compound "Ref" in Formula 16, Compound E1 ("HBL-1-1") in Formula 8, and Compound F1 ("HBL-2-1") in Formula 10 are each used to form the HBL.

[0344] (21) Examples 61 to 63 (Ex61 to Ex63)

[0345] Compound H-9 ("EBL-2") in Formula 6 is used to form the EBL, Compound 1-13 in Formula 3 serves as a dopant, and Compound 2-7 in Formula 4 serves as a host to form the EML. Compound "Ref" in Formula 16, Compound E1 ("HBL-1-1") in Formula 8, and Compound F1 ("HBL-2-1") in Formula 10 are each used to form the HBL.

[0346] (22) Examples 64 to 66 (Ex64 to Ex66)

[0347] Compound "Ref" in Formula 15 is used to form the EBL, compounds 1-13 in Formula 3 serve as dopants, and compounds 2-9 in Formula 4 serve as hosts to form the EML. Compound "Ref" in Formula 16, compound E1 in Formula 8 ("HBL-1-1"), and compound F1 in Formula 10 ("HBL-2-1") are each used to form the HBL.

[0348] (23) Examples 67 to 69 (Ex67 to Ex69)

[0349] Compound H-3 ("EBL-1") in Formula 6 is used to form the EBL, Compound 1-13 in Formula 3 serves as a dopant, and Compound 2-9 in Formula 4 serves as a host to form the EML. Compound "Ref" in Formula 16, Compound E1 ("HBL-1-1") in Formula 8, and Compound F1 ("HBL-2-1") in Formula 10 are each used to form the HBL.

[0350] (24) Examples 70 to 72 (Ex70 to Ex72)

[0351] Compound H-9 ("EBL-2") in Formula 6 is used to form the EBL, Compound 1-13 in Formula 3 serves as a dopant, and Compound 2-9 in Formula 4 serves as a host to form the EML. Compound "Ref" in Formula 16, Compound E1 ("HBL-1-1") in Formula 8, and Compound F1 ("HBL-2-1") in Formula 10 are each used to form the HBL.

[0352] [Equation 15]

[0353]

[0354] [Equation 16]

[0355]

[0356] The properties of the OLEDs manufactured in Comparative Examples 1 to 8 and Examples 1 to 72, namely, driving voltage (V), external quantum efficiency (EQE), color coordinates (CIE) and lifetime (T 95 ), and listed them in Tables 1 to 8.

[0357] Table 1

[0358] EBL D H HBL V EQE(%) CIE(x) CIE(y) <![CDATA[T 95 (hr)]]> Ref1 Ref. 1-6 2-1 Ref. 3.93 3.11 0.140 0.076 26 Ex1 Ref. 1-6 2-7 Ref. 3.95 3.09 0.140 0.075 45 Ex2 Ref. 1-6 2-7 HBL-1-1 3.95 3.14 0.141 0.074 54 Ex3 Ref. 1-6 2-7 HBL-2-1 3.91 3.19 0.140 0.075 61 Ex4 EBL-1 1-6 2-7 Ref. 3.95 6.11 0.139 0.078 136 Ex5 EBL-1 1-6 2-7 HBL-1-1 3.91 6.24 0.140 0.074 180 Ex6 EBL-1 1-6 2-7 HBL-2-1 3.89 6.35 0.140 0.074 213 Ex7 EBL-2 1-6 2-7 Ref. 3.95 6.43 0.139 0.077 123 Ex8 EBL-2 1-6 2-7 HBL-1-1 3.92 6.58 0.139 0.075 168 Ex9 EBL-2 1-6 2-7 HBL-2-1 3.92 6.67 0.140 0.074 198

[0359] Table 2

[0360] EBL D H HBL V EQE(%) CIE(x) CIE(y) <![CDATA[T 95 (hr)]]> Ref2 Ref. 1-6 2-3 Ref. 3.82 3.01 0.139 0.076 28 Ex10 Ref. 1-6 2-9 Ref. 3.84 3.03 0.138 0.081 38 Ex11 Ref. 1-6 2-9 HBL-1-1 3.81 3.09 0.137 0.080 49 Ex12 Ref. 1-6 2-9 HBL-2-1 3.82 3.19 0.138 0.081 58 Ex13 EBL-1 1-6 2-9 Ref. 3.85 6.05 0.139 0.080 125 Ex14 EBL-1 1-6 2-9 HBL-1-1 3.79 6.13 0.137 0.081 162 Ex15 EBL-1 1-B 2-9 HBL-2-1 3.80 6.31 0.137 0.082 195 Ex16 EBL-2 1-6 2-9 Ref. 3.83 6.36 0.138 0.081 119 Ex17 EBL-2 1-6 2-9 HBL-1-1 3.79 6.42 0.138 0.079 152 Ex18 EBL-2 1-6 2-9 HBL-2-1 3.81 6.60 0.138 0.081 189

[0361] Table 3

[0362] EBL D H HBL V EQE(%) CIE(x) CIE(y) <![CDATA[T 95 (hr)]]> Ref3 Ref. 1-8 2-1 Ref. 3.92 3.12 0.136 0.081 28 Ex19 Ref. 1-8 2-7 Ref. 3.93 3.08 0.139 0.082 42 Ex20 Ref. 1-8 2-7 HBL-1-1 3.87 3.17 0.137 0.081 50 Ex21 Ref. 1-8 2-7 HBL-2-1 3.91 3.22 0.137 0.082 59 Ex22 EBL-1 1-8 2-7 Ref. 3.92 6.17 0.138 0.082 133 Ex23 EBL-1 1-8 2-7 HBL-1-1 3.88 6.32 0.138 0.080 166 Ex24 EBL-1 1-8 2-7 HBL-2-1 3.90 6.40 0.137 0.081 195 Ex25 EBL-2 1-8 2-7 Ref. 3.88 6.48 0.138 0.081 132 Ex26 EBL-2 1-8 2-7 HBL-1-1 3.86 6.60 0.138 0.081 158 Ex27 EBL-2 1-8 2-7 HBL-2-1 3.89 6.69 0.136 0.082 186

[0363] Table 4

[0364] EBL D H HBL V EQE(%) CIE(x) CIE(y) <![CDATA[T 95 (hr)]]> Ref4 1-8 2-3 Ref. 3.80 3.05 0.137 0.081 27 Ref. Ex28 1-8 2-9 Ref. 3.81 3.07 0.138 0.083 36 Ref. Ex29 1-8 2-9 Ref. 3.76 3.06 0.137 0.083 42 HBL-1-1 Ex30 1-8 2-9 Ref. 3.80 3.18 0.137 0.083 52 HBL-2-1 Ex31 1-8 2-9 EBL-1 3.82 6.08 0.137 0.083 119 Ref. Ex32 1-8 2-9 EBL-1 3.80 6.15 0.136 0.084 147 HBL-1-1 Ex33 1-8 2-9 EBL-1 3.79 6.32 0.136 0.084 175 HBL-2-1 Ex34 1-8 2-9 EBL-2 3.84 6.39 0.138 0.082 114 Ref. Ex35 1-8 2-9 EBL-2 3.76 6.42 0.136 0.084 144 HBL-1-1 Ex36 1-8 2-9 EBL-2 3.81 6.65 0.137 0.081 161

[0365] Table 5

[0366] HBL-2-1 D H EBL V HBL EQE(%) CIE(x) <![CDATA[T 95 (hr)]]> CIE(y) Ref5 1-11 2-1 Ref. 3.95 3.08 0.141 0.076 40 Ref. Ex37 1-11 2-7 Ref 3.94 3.04 0.140 0.074 68 Ref. Ex38 1-11 2-7 Ref. 3.94 3.09 0.140 0.076 80 HBL-1-1 Ex39 1-11 2-7 Ref. 3.90 3.14 0.140 0.076 92 HBL-2-1 Ex40 1-11 2-7 EBL-1 3.96 6.18 0.139 0.075 205 Ref. Ex41 1-11 2-7 EBL-1 3.90 6.20 0.140 0.074 270 HBL-1-1 Ex42 1-11 2-7 EBL-1 3.90 6.29 0.140 0.074 319 HBL-2-1 Ex43 1-11 2-7 EBL-2 3.96 6.41 0.139 0.076 184 Ref. Ex44 1-11 2-7 EBL-2 3.94 6.52 0.140 0.075 251 HBL-1-1 Ex45 1-11 2-7 EBL-2 3.91 6.58 0.140 0.074 297

[0367] Table 6

[0368] HBL-2-1 D H EBL V HBL EQE(%) CIE(x) <![CDATA[T 95 (hr)]]> CIE(y) Ref6 1-11 2-3 Ref. 3.83 2.99 0.140 0.077 42 Ref. 1-11 2-9 Ex46 3.82 2.98 0.138 0.083 57 Ref. Ref. 1-11 2-9 Ex47 3.82 3.04 0.137 0.080 74 Ref. HBL-1-1 1-11 2-9 Ex48 3.84 3.20 0.138 0.083 87 Ref. HBL-2-1 1-11 2-9 Ex49 3.84 6.09 0.139 0.080 187 EBL-1 Ref. 1-11 2-9 [[ID=z12]]Ex50 3.81 6.18 0.138 0.081 243 EBL-1 HBL-1-1 1-11 2-9 Ex51 3.82 6.21 0.139 0.076 292 EBL-1 HBL-2-1 1-11 2-9 Ex52 EBL-2 Ref. 3.85 6.32 0.138 0.081 178 Ex53 EBL-2 1-11 2-9 HBL-1-1 3.81 6.39 0.139 0.075 228 Ex54 EBL-2 1-11 2-9 HBL-2-1 3.84 6.63 0.139 0.081 283

[0369] Table 7

[0370] EBL D H HBL V EQE (%) CIE(x) CIE(y) <![CDATA[T 95 (hr)]]> Ref7 Ref. 1-13 2-1 Ref. 3.90 3.11 0.138 0.082 42 Ex55 Ref. 1-13 2-7 Ref. 3.95 3.01 0.139 0.084 63 Ex56 Ref. 1-13 2-7 HBL-1-1 3.85 3.14 0.137 0.083 74 Ex57 Ref. 1-13 2-7 HBL-2-1 3.93 3.18 0.137 0.085 89 Ex58 EBL-1 1-13 2-7 Ref. 3.91 6.08 0.138 0.084 199 Ex59 EBL-1 1-13 2-7 HBL-1-1 3.86 6.27 0.138 0.084 250 Ex60 EBL-1 1-13 2-7 HBL-2-1 3.92 6.38 0.137 0.085 293 Ex61 EBL-2 1-13 2-7 Ref. 3.89 6.39 0.138 0.083 201 Ex62 EBL-2 1-13 2-7 HBL-1-1 3.87 6.54 0.138 0.084 238 Ex63 EBL-2 1-13 2-7 HBL-2-1 3.87 6.52 0.136 0.084 279

[0371] Table 8

[0372] EBL D H HBL V EQE (%) CIE(x) CIE(y) <![CDATA[T 95 (hr)]]> Ref8 Ref. 1-13 2-3 Ref. 3.84 3.00 0.137 0.082 41 Ex64 Ref. 1-13 2-9 Ref. 3.82 3.09 0.139 0.083 53 Ex65 Ref. 1-13 2-9 HBL-1-1 3.75 3.03 0.138 0.083 63 Ex66 Ref. 1-13 2-9 HBL-2-1 3.82 3.20 0.137 0.083 78 Ex67 EBL-1 1-13 2-9 Ref. 3.83 6.01 0.137 0.083 179 Ex68 EBL-1 1-13 2-9 HBL-1-1 3.81 6.18 0.137 0.085 221 Ex69 EBL-1 1-13 2-9 HBL-2-1 3.81 6.29 0.138 0.084 262 Ex70 EBL-2 1-13 2-9 Ref. 3.86 6.40 0.138 0.084 177 Ex71 EBL-2 1-13 2-9 HBL-1-1 3.74 6.35 0.137 0.084 223 Ex72 EBL-2 1-13 2-9 HBL-2-1 3.84 6.49 0.137 0.083 250

[0373] As shown in Tables 1 to 8, the OLEDs Ex1 to Ex72, each of which includes a deuterated anthracene derivative (e.g., Compound 2-7 or 2-9) as a host, have significantly improved luminous efficiency and lifetime compared to the OLEDs Ref1 to Ref8, each of which includes a non-deuterated anthracene derivative (e.g., Compound 2-1 or 2-3) as a host.

[0374] In addition, the OLEDs of Ex1 to Ex9, Ex19 to Ex27, Ex37 to Ex45, and Ex55 to Ex63, each of which includes the compound 2-7 as a host, have increased luminous efficiency and lifetime compared to the OLEDs of Ex10 to Ex18, Ex28 to Ex36, Ex46 to Ex54, and Ex64 to Ex72, each of which includes the compound 2-9 as a host. That is, when a deuterated anthracene derivative (in which one naphthalene moiety (i.e., 1-naphthyl) is directly attached to one side of the anthracene moiety and the other naphthalene moiety (i.e., 2-naphthyl) is attached to the other side of the anthracene moiety directly or through a linker) is included as a host, the luminous efficiency and lifetime of the OLED are increased.

[0375] Furthermore, when a boron derivative having an asymmetric structure, such as Compound 1-6, 1-8, 1-11, or 1-13, is used as a dopant, the luminous efficiency and lifetime of the OLED are improved.

[0376] Furthermore, when a deuterated boron derivative having an asymmetric structure, such as Compound 1-11, 1-12, 1-13, or 1-17, is used as a dopant, the luminous efficiency and lifetime of the OLED are further improved.

[0377] In addition, when R 81 and R 82 When the compounds of Formula 1-2, each of which is an aryl (phenyl) group substituted with an alkyl (tert-butyl) group, such as Compound 1-6 or 1-11, are used as a dopant, the luminous efficiency and lifespan of the OLED are further improved.

[0378] In addition, when the HBL includes the compound of Formula 8 or the compound of Formula 10, the luminous efficiency and lifespan of the OLED are improved.

[0379] Furthermore, when the EBL includes the compound of Formula 6, the luminous efficiency and lifetime of the OLED are significantly improved.

[0380] In addition, when the EML has Compound 2-7 or 2-9 as a deuterated anthracene derivative and Compound 1-2 as a boron derivative, the EBL has the compound of Formula 5, and the HBL has the compound of Formula 7 or 9, the luminous efficiency and lifespan of the OLED are significantly improved.

[0381] Figure 4is a schematic cross-sectional view illustrating an OLED having a tandem structure of two emission parts according to a first embodiment of the present disclosure.

[0382] like Figure 4 As shown, the OLED D includes a first electrode 160 and a second electrode 164 facing each other, and an organic light-emitting layer 162 between the first electrode 160 and the second electrode 164. The organic light-emitting layer 162 includes: a first emission portion 310 including a first EML 320, a first EBL 316, and a first HBL 318; a second emission portion 330 including a second EML 340, a second EBL 334, and a second HBL 336; and a charge generation layer (CGL) 350 between the first emission portion 310 and the second emission portion 330. The organic light-emitting display device 100 ( Figure 2 ) includes a red pixel, a green pixel and a blue pixel, and the OLED D can be located in the blue pixel.

[0383] One of the first electrode 160 and the second electrode 164 is an anode, and the other is a cathode. One of the first electrode 160 and the second electrode 164 is a transmissive electrode (or a semi-transmissive electrode), and the other is a reflective electrode.

[0384] The CGL 350 is located between the first emitting portion 310 and the second emitting portion 330, and the first emitting portion 310, the CGL 350, and the second emitting portion 330 are sequentially stacked on the first electrode 160. That is, the first emitting portion 310 is located between the first electrode 160 and the CGL 350, and the second emitting portion 330 is located between the second electrode 164 and the CGL 350.

[0385] The first emission portion 310 may further include a first HTL 314 between the first electrode 160 and the first EBL 316 , and a HIL 312 between the first electrode 160 and the first HTL 314 .

[0386] First EML 320 includes a dopant 322 of a boron derivative and a host 324 of a deuterated anthracene derivative and emits blue light. Specifically, at least one hydrogen atom in the anthracene derivative is replaced by deuterium. The boron derivative is not deuterated, or some hydrogen atoms in the boron derivative are replaced by deuterium. Dopant 322 can be represented by Formula 1-1 or 1-2 and can be one of the compounds shown in Formula 3. Host 324 can be represented by Formula 2 and can be one of the compounds shown in Formula 4.

[0387] In the first EML 320, the host 324 may be about 70 to 99.9 wt%, and the dopant 322 may be about 0.1 to 30 wt%. To provide sufficient luminous efficiency, the dopant 322 may be about 0.1 to 10 wt%, preferably about 1 to 5 wt%.

[0388] The first EBL 316 may include the compound of Formula 5 as the electron blocking material 317. The first HBL 318 may include at least one of the compound of Formula 7 and the compound of Formula 9 as the hole blocking material 319. For example, the first HBL 318 may include the compound of Formula 7 and the compound of Formula 9 at the same weight %.

[0389] The second emission section 330 may further include a second HTL 332 between the CGL 350 and the second EBL 334 , and an EIL 338 between the second HBL 336 and the second electrode 164 .

[0390] The second EML 340 includes a dopant 342 of a boron derivative and a host 344 of a deuterated anthracene derivative and emits blue light. That is, at least one hydrogen in the anthracene derivative is replaced by deuterium. The boron derivative is not deuterated, or some hydrogen in the boron derivative is replaced by deuterium.

[0391] In the second EML 340, the host 344 may be about 70 to 99.9 wt%, and the dopant 342 may be about 0.1 to 30 wt%. To provide sufficient luminous efficiency, the dopant 342 may be about 0.1 to 10 wt%, preferably about 1 to 5 wt%.

[0392] The body 344 of the second EML 340 may be the same as or different from the body 324 of the first EML 320 , and the dopant 342 of the second EML 340 may be the same as or different from the dopant 322 of the first EML 320 .

[0393] The second EBL 334 may include the compound of Formula 5 as the electron blocking material 335. The second HBL 336 may include at least one of the compound of Formula 7 and the compound of Formula 9 as the hole blocking material 337. For example, the second HBL 336 may include the compound of Formula 7 and the compound of Formula 9 at the same weight %.

[0394] The CGL 350 is located between the first emitting portion 310 and the second emitting portion 330. That is, the first emitting portion 310 and the second emitting portion 330 are connected through the CGL 350. The CGL 350 may be a PN junction CGL of an N-type CGL 352 and a P-type CGL 354.

[0395] The N-type CGL 352 is located between the first HBL 318 and the second HTL 332 , and the P-type CGL 354 is located between the N-type CGL 352 and the second HTL 332 .

[0396] In the OLED D, the first and second EMLs 320 and 340 each include dopants 322 and 342 that are boron derivatives and hosts 324 and 344 that are deuterated anthracene derivatives. As a result, the OLED D and the organic light emitting display device 100 have advantages in luminous efficiency and lifespan.

[0397] When the boron derivatives as the dopants 322 and 342 have an asymmetric structure as shown in Formula 1-2, the luminous efficiency and lifespan of the OLED D and the organic light emitting display device 100 are further improved.

[0398] Furthermore, when boron derivatives in which aromatic and heteroaromatic rings other than the benzene ring bonded to the boron atom and two nitrogen atoms are partially or completely deuterated are included as dopants 322 and 342 , luminous efficiency and lifespan of OLED D and organic light-emitting display device 100 are further improved.

[0399] Furthermore, when the anthracene derivatives as the hosts 324 and 344 include two naphthalene moieties connected to an anthracene moiety and are partially or fully deuterated, the luminous efficiency and lifespan of the OLED D and the organic light emitting display device 100 including the anthracene derivatives are further improved.

[0400] In addition, since at least one of the first EBL 316 and the second EBL 334 includes the compound of Formula 5 as an electron blocking material and each of the first HBL 318 and the second HBL 336 includes at least one of the compound of Formula 7 and the compound of Formula 9 as a hole blocking material, the luminous efficiency and lifespan of the OLED D and the organic light emitting display device 100 are further improved.

[0401] In addition, since the first emission part 310 and the second emission part 330 for emitting blue light are stacked, the organic light emitting display device 100 provides an image with a high color temperature.

[0402] Figure 5 is a schematic cross-sectional view showing an organic light emitting display device according to a second embodiment of the present disclosure, Figure 6 is a schematic cross-sectional view illustrating an OLED having a tandem structure of two emission parts according to a second embodiment of the present disclosure. Figure 7 is a schematic cross-sectional view illustrating an OLED having a tandem structure of three emission parts according to a second embodiment of the present disclosure.

[0403] like Figure 5As shown, the organic light emitting display device 400 includes a first substrate 410 in which red pixels RP, green pixels GP, and blue pixels BP are defined, a second substrate 470 facing the first substrate 410, an OLED D located between the first substrate 410 and the second substrate 470 and providing white light emission, and a color filter layer 480 between the OLED D and the second substrate 470.

[0404] The first substrate 410 and the second substrate 470 may each be a glass substrate or a flexible substrate. For example, the flexible substrate may be one of a polyimide (PI) substrate, polyethersulfone (PES), polyethylene naphthalate (PEN), polyethylene terephthalate (PET), and polycarbonate (PC).

[0405] A buffer layer 420 is formed on the first substrate, and respective TFTs Tr corresponding to the red pixel RP, the green pixel GP, and the blue pixel BP are formed on the buffer layer 420. The buffer layer 420 may be omitted.

[0406] The semiconductor layer 422 is formed on the buffer layer 420. The semiconductor layer 422 may include an oxide semiconductor material or polysilicon.

[0407] A gate insulating layer 424 is formed on the semiconductor layer 422. The gate insulating layer 424 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride.

[0408] The gate 430 formed of a conductive material such as metal is formed on the gate insulating layer 424 corresponding to the center of the semiconductor layer 422 .

[0409] An interlayer insulating layer 432 formed of an insulating material is formed on the gate electrode 430. The interlayer insulating layer 432 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride or an organic insulating material such as benzocyclobutene or photo acryl.

[0410] The interlayer insulating layer 432 includes a first contact hole 434 and a second contact hole 436 exposing both sides of the semiconductor layer 422. The first contact hole 434 and the second contact hole 436 are located on both sides of the gate 430 to be spaced apart from the gate 430.

[0411] A source electrode 440 and a drain electrode 442 formed of a conductive material such as metal are formed on the interlayer insulating layer 432 .

[0412] The source electrode 440 and the drain electrode 442 are spaced apart from each other relative to the gate electrode 430 , and contact two sides of the semiconductor layer 422 through the first contact hole 434 and the second contact hole 436 , respectively.

[0413] The semiconductor layer 422, the gate electrode 430, the source electrode 440, and the drain electrode 442 constitute a TFT Tr. The TFT Tr serves as a driving element. That is, the TFT Tr may correspond to the driving TFT Td ( Figure 1 ).

[0414] Although not shown, the gate lines and the data lines cross each other to define pixels, and a switching TFT is formed to be connected to the gate lines and the data lines. The switching TFT is connected to a TFT Tr as a driving element.

[0415] In addition, a power supply line (which may be formed parallel to and spaced apart from one of the gate line and the data line) and a storage capacitor for maintaining a voltage of the gate electrode of the TFT Tr in one frame may be further formed.

[0416] A passivation layer (or planarization layer) 450 is formed to cover the TFT Tr, and includes a drain contact hole 452 exposing the drain electrode 442 of the TFT Tr.

[0417] A first electrode 460 connected to the drain electrode 442 of the TFT Tr through the drain contact hole 452 is formed separately in each pixel and on the passivation layer 450. The first electrode 460 may be an anode and may be formed of a conductive material having a relatively high work function, such as a transmissive conductive oxide (TCO). For example, the first electrode 460 may be formed of indium tin oxide (ITO), indium zinc oxide (IZO), indium tin zinc oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium copper oxide (ICO), or aluminum zinc oxide (Al:ZnO, AZO).

[0418] When the organic light-emitting display device 400 operates in a bottom-emission mode, the first electrode 460 may have a single-layer structure of a transmissive conductive oxide. When the organic light-emitting display device 400 operates in a top-emission mode, a reflective electrode or reflective layer may be formed below the first electrode 460. For example, the reflective electrode or reflective layer may be formed of silver (Ag) or an aluminum-palladium-copper (APC) alloy. In this case, the first electrode 460 may have a three-layer structure of ITO / Ag / ITO or ITO / APC / ITO.

[0419] A bank layer 466 is formed on the passivation layer 450 to cover the edge of the first electrode 460. That is, the bank layer 466 is located at the boundary of the pixel and exposes the center of the first electrode 460 in the pixel. Since the OLED D emits white light in the red pixel RP, the green pixel GP, and the blue pixel BP, the organic light-emitting layer 462 can be formed as a common layer in the red pixel RP, the green pixel GP, and the blue pixel BP without being separated. The bank layer 466 can be formed to prevent leakage at the edge of the first electrode 460, or the bank layer 466 can be omitted.

[0420] The organic light emitting layer 462 is formed on the first electrode 460 .

[0421] See also Figure 6 OLED D includes a first electrode 460 and a second electrode 464 facing each other, and an organic light-emitting layer 462 between the first electrode 460 and the second electrode 464. Organic light-emitting layer 462 includes a first emission portion 710 including a first EML 720, a first EBL 716, and a first HBL 718; a second emission portion 730 including a second EML 740, a second EBL 734, and a second HBL 736; and a charge generation layer (CGL) 750 between the first emission portion 710 and the second emission portion 730.

[0422] The CGL 750 is located between the first emitting portion 710 and the second emitting portion 730, and the first emitting portion 710, the CGL 750, and the second emitting portion 730 are sequentially stacked on the first electrode 460. That is, the first emitting portion 710 is located between the first electrode 460 and the CGL 750, and the second emitting portion 730 is located between the second electrode 464 and the CGL 750.

[0423] The first emission portion 710 may further include a first HTL 714 between the first electrode 460 and the first EBL 716 , and a HIL 712 between the first electrode 460 and the first HTL 714 .

[0424] First EML 720 includes a boron derivative dopant 722 and a deuterated anthracene derivative host 724, and emits blue light. Specifically, at least one hydrogen atom in the anthracene derivative is replaced by deuterium. The boron derivative is not deuterated, or some hydrogen atoms in the boron derivative are replaced by deuterium. Dopant 722 can be represented by Formula 1-1 or 1-2 and can be one of the compounds shown in Formula 3. Host 724 can be represented by Formula 2 and can be one of the compounds shown in Formula 4.

[0425] In the first EML 720, the host 724 may be about 70 to 99.9 wt%, and the dopant 722 may be about 0.1 to 30 wt%. To provide sufficient luminous efficiency, the dopant 722 may be about 0.1 to 10 wt%, preferably about 1 to 5 wt%.

[0426] The first EBL 716 may include the compound of Formula 5 as the electron blocking material 717. The first HBL 718 may include at least one of the compound of Formula 7 and the compound of Formula 9 as the hole blocking material 719. For example, the first HBL 718 may include the compound of Formula 7 and the compound of Formula 9 at the same weight %.

[0427] In addition, the second emission portion 730 may further include a second HTL 732 between the CGL 750 and the second EBL 734 , and an EIL 738 between the second HBL 736 and the second electrode 464 .

[0428] The second EML 740 may be a yellow-green EML. For example, the second EML 740 may include a yellow-green dopant 743 and a host 745. The yellow-green dopant 743 may be one of a fluorescent compound, a phosphorescent compound, and a delayed fluorescent compound.

[0429] In the second EML 740, the host 745 may be about 70 to 99.9 wt%, and the yellow-green dopant 743 may be about 0.1 to 30 wt%. To provide sufficient luminous efficiency, the yellow-green dopant 743 may be about 0.1 to 10 wt%, preferably about 1 to 5 wt%.

[0430] The second EBL 734 may include the compound of Formula 5 as the electron blocking material 735. The second HBL 736 may include at least one of the compound of Formula 7 and the compound of Formula 9 as the hole blocking material 737. For example, the second HBL 736 may include the compound of Formula 7 and the compound of Formula 9 at the same weight %.

[0431] The CGL 750 is located between the first emitting portion 710 and the second emitting portion 730. That is, the first emitting portion 710 and the second emitting portion 730 are connected through the CGL 750. The CGL 750 may be a PN junction CGL of an N-type CGL 752 and a P-type CGL 754.

[0432] The N-type CGL 752 is located between the first HBL 718 and the second HTL 732 , and the P-type CGL 754 is located between the N-type CGL 752 and the second HTL 732 .

[0433] exist Figure 6 , the first EML 720 located between the first electrode 460 and the CGL 750 includes a host 722 of an anthracene derivative and a dopant 724 of a boron derivative, and the second EML 740 located between the second electrode 464 and the CGL 750 is a yellow-green EML. Alternatively, the first EML 720 located between the first electrode 460 and the CGL 750 may be a yellow-green EML, and the second EML 740 located between the second electrode 464 and the CGL 750 may include a host of an anthracene derivative and a dopant of a boron derivative, and be a blue EML.

[0434] In the OLED D, the first EML 720 includes dopants 722 each being a boron derivative and hosts 724 each being a deuterated anthracene derivative. As a result, the OLED D and the organic light emitting display device 400 have advantages in terms of luminous efficiency and lifespan.

[0435] When the boron derivative as the dopant 722 has an asymmetric structure as shown in Formula 1-2, the luminous efficiency and lifespan of the OLED D and the organic light emitting display device 400 are further improved.

[0436] Furthermore, when a boron derivative in which aromatic rings and heteroaromatic rings other than the benzene ring bonded to the boron atom and two nitrogen atoms are partially or completely deuterated is included as the dopant 722 , the luminous efficiency and lifespan of the OLED D and the organic light emitting display device 400 are further improved.

[0437] Furthermore, when the anthracene derivative as the host 724 includes two naphthalene moieties connected to an anthracene moiety and is partially or fully deuterated, the luminous efficiency and lifespan of the OLED D and the organic light emitting display device 400 including the anthracene derivative are further improved.

[0438] In addition, since at least one of the first EBL 716 and the second EBL 734 includes the compound of Formula 5 as an electron blocking material, and each of the first HBL 718 and the second HBL 736 includes at least one of the compound of Formula 7 and the compound of Formula 9 as a hole blocking material, the luminous efficiency and lifespan of the OLED D and the organic light emitting display device 400 are further improved.

[0439] In addition, the OLED D including the first emission part 710 and the second emission part 730 providing yellow-green emission emits white light.

[0440] See also Figure 7 The organic light-emitting layer 462 includes: a first emission portion 530 including a first EML 520, a first EBL 536 and a first HBL 538, a second emission portion 550 including a second EML 540, a third emission portion 570 including a third EML 560, a second EBL 574 and a second HBL 576, a first CGL 580 between the first emission portion 530 and the second emission portion 550, and a second CGL 590 between the second emission portion 550 and the third emission portion 570.

[0441] The first CGL 580 is located between the first emitting section 530 and the second emitting section 550, and the second CGL 590 is located between the second emitting section 550 and the third emitting section 570. That is, the first emitting section 530, the first CGL 580, the second emitting section 550, the second CGL 590, and the third emitting section 570 are stacked in sequence on the first electrode 460. In other words, the first emitting section 530 is located between the first electrode 460 and the first CGL 580, the second emitting section 550 is located between the first CGL 580 and the second CGL 590, and the third emitting section 570 is located between the second electrode 464 and the second CGL 590.

[0442] The first emission portion 530 may include at least one of a first HTL 534 located between the first electrode 460 and the first EBL 546, and a HIL 532 located between the first electrode 460 and the first HTL 534. For example, the HIL 532, the first HTL 534, and the first EBL 536 may be sequentially stacked between the first electrode 460 and the first EML 520, and the first HBL 538 may be located between the first EML 520 and the first CGL 580.

[0443] First EML 520 includes a dopant 522 of a boron derivative and a host 524 of a deuterated anthracene derivative and emits blue light. Specifically, at least one hydrogen atom in the anthracene derivative is replaced by deuterium. The boron derivative is not deuterated, or some hydrogen atoms in the boron derivative are replaced by deuterium. Dopant 522 can be represented by Formula 1-1 or 1-2 and can be one of the compounds shown in Formula 3. Host 524 can be represented by Formula 2 and can be one of the compounds shown in Formula 4.

[0444] In the first EML 520, the host 524 may be about 70 to 99.9 wt%, and the dopant 522 may be about 0.1 to 30 wt%. To provide sufficient emission efficiency, the dopant 522 may be about 0.1 to 10 wt%, preferably 1 to 5 wt%.

[0445] The first EBL 536 may include the compound of Formula 5 as the electron blocking material 537. The first HBL 538 may include at least one of the compound of Formula 7 and the compound of Formula 9 as the hole blocking material 539. For example, the first HBL 538 may include both the compound of Formula 7 and the compound of Formula 9 at the same weight %.

[0446] The second emission portion 550 may further include a second HTL 552 and an electron transport layer (ETL) 554. The second HTL 552 is located between the first CGL 580 and the second EML 540, and the ETL 554 is located between the second EML 540 and the second CGL 590.

[0447] The second EML 540 may be a yellow-green EML. For example, the second EML 540 may include a host and a yellow-green dopant.

[0448] Alternatively, the second EML 540 may include a host, a red dopant, and a green dopant. In this case, the second EML 540 may have a single-layer structure, or may have a double-layer structure including a lower layer including a host and a red dopant (or a green dopant) and an upper layer including a host and a green dopant (or a red dopant).

[0449] The second EML 540 may have a triple-layered structure of a first layer including a host and a red dopant, a second layer including a host and a yellow-green dopant, and a third layer including a host and a green dopant.

[0450] The third emission part 570 may further include at least one of a third HTL 572 under the second EBL 574 and an EIL 578 over the second HBL 576 .

[0451] Third EML 560 includes a dopant 562 of a boron derivative and a host 564 of a deuterated anthracene derivative and emits blue light. That is, at least one hydrogen in the anthracene derivative is replaced by deuterium. The boron derivative is not deuterated, or some hydrogen in the boron derivative is replaced by deuterium. Dopant 562 can be represented by Formula 1-1 or 1-2 and can be one of the compounds in Formula 3. Host 564 can be represented by Formula 2 and can be one of the compounds in Formula 4.

[0452] In the third EML 560, the host 564 may be about 70 to 99.9 wt%, and the dopant 562 may be about 0.1 to 30 wt%. To provide sufficient luminous efficiency, the dopant 562 may be about 0.1 to 10 wt%, preferably about 1 to 5 wt%.

[0453] The body 564 of the third EML 560 may be the same as or different from the body 524 of the first EML 520 , and the dopant 562 of the third EML 560 may be the same as or different from the dopant 522 of the first EML 520 .

[0454] The second EBL 574 may include the compound of Formula 5 as the electron blocking material 575. The second HBL 576 may include at least one of the compound of Formula 7 and the compound of Formula 9 as the hole blocking material 577. For example, the second HBL 576 may include both the compound of Formula 7 and the compound of Formula 9 at the same weight %.

[0455] The first CGL 580 is located between the first emitting portion 530 and the second emitting portion 550, and the second CGL 590 is located between the second emitting portion 550 and the third emitting portion 570. That is, the first emitting portion 530 and the second emitting portion 550 are connected via the first CGL 580, and the second emitting portion 550 and the third emitting portion 570 are connected via the second CGL 590. The first CGL 580 may be a PN junction CGL formed by a first N-type CGL 582 and a first P-type CGL 584, and the second CGL 590 may be a PN junction CGL formed by a second N-type CGL 592 and a second P-type CGL 594.

[0456] In the first CGL 580 , a first N-type CGL 582 is located between the first HBL 538 and the second HTL 552 , and a first P-type CGL 584 is located between the first N-type CGL 582 and the second HTL 552 .

[0457] In the second CGL 590 , a second N-type CGL 592 is located between the ETL 554 and the third HTL 572 , and a second P-type CGL 594 is located between the second N-type CGL 592 and the third HTL 572 .

[0458] In the OLED D, the first and third EMLs 520 and 560 each include dopants 522 and 562 each being a boron derivative and hosts 524 and 564 each being a deuterated anthracene derivative. As a result, the OLED D and the organic light emitting display device 400 have advantages in luminous efficiency and lifespan.

[0459] When the boron derivatives as the dopants 522 and 562 have an asymmetric structure as shown in Formula 1-2, the luminous efficiency and lifespan of the OLED D and the organic light-emitting display device 400 are further improved.

[0460] Furthermore, when boron derivatives in which aromatic and heteroaromatic rings other than the benzene ring bonded to the boron atom and two nitrogen atoms are partially or completely deuterated are included as dopants 522 and 562 , the luminous efficiency and lifespan of OLED D and organic light-emitting display device 400 are further improved.

[0461] Furthermore, when the anthracene derivatives as the hosts 524 and 564 include two naphthalene moieties connected to an anthracene moiety and are partially or fully deuterated, the luminous efficiency and lifespan of the OLED D and the organic light-emitting display device 400 including the anthracene derivatives are further improved.

[0462] In addition, since at least one of the first EBL 536 and the second EBL 574 includes the compound of Formula 5 as an electron blocking material and each of the first HBL 538 and the second HBL 576 includes at least one of the compound of Formula 7 and the compound of Formula 9 as a hole blocking material, the luminous efficiency and lifespan of the OLED D and the organic light emitting display device 400 are further improved.

[0463] In addition, the OLED D including the first and third emission parts 530 and 570 and the second emission part 550 emitting yellow-green light or red-green light may emit white light.

[0464] exist Figure 7 , the OLED D has a triple stack structure of a first emission part 530, a second emission part 550, and a third emission part 570. Alternatively, the OLED D may further include other emission parts and a CGL.

[0465] See again Figure 5 , a second electrode 464 is formed on the substrate 410 on which the organic light emitting layer 462 is formed.

[0466] In the organic light emitting display device 400 , since light emitted from the organic light emitting layer 462 is incident on the color filter layer 480 through the second electrode 464 , the second electrode 464 has a thin profile for transmitting the light.

[0467] The first electrode 460 , the organic light emitting layer 462 , and the second electrode 464 constitute an OLED D.

[0468] Color filter layer 480 is positioned over OLED D and includes red, green, and blue filters 482, 484, and 486 corresponding to red, green, and blue pixels RP, GP, and BP, respectively. Red filter 482 may include at least one of a red dye and a red pigment, green filter 484 may include at least one of a green dye and a green pigment, and blue filter 486 may include at least one of a blue dye and a blue pigment.

[0469] Although not shown, the color filter layer 480 may be attached to the OLED D using an adhesive layer. Alternatively, the color filter layer 480 may be formed directly on the OLED D.

[0470] An encapsulation film (not shown) may be formed to prevent moisture from penetrating into the OLED D. For example, the encapsulation film may include a first inorganic insulating layer, an organic insulating layer, and a second inorganic insulating layer stacked in sequence, but is not limited thereto. The encapsulation film may be omitted.

[0471] A polarizing plate (not shown) for reducing ambient light reflection may be disposed above the top emission type OLED D. For example, the polarizing plate may be a circular polarizing plate.

[0472] exist Figure 5 In the OLED D, the first electrode 460 and the second electrode 464 are a reflective electrode and a transmissive (or semi-transmissive) electrode, respectively, and the color filter layer 480 is disposed over the OLED D. Alternatively, when the first electrode 460 and the second electrode 464 are a transmissive (or semi-transmissive) electrode and a reflective electrode, respectively, the color filter layer 480 may be disposed between the OLED D and the first substrate 410.

[0473] A color conversion layer (not shown) may be formed between the OLED D and the color filter layer 480. The color conversion layer may include a red conversion layer, a green conversion layer, and a blue conversion layer corresponding to the red pixel RP, the green pixel GP, and the blue pixel BP, respectively. White light from the OLED D is converted into red light, green light, and blue light by the red, green, and blue conversion layers, respectively. For example, the color conversion layer may include quantum dots. As a result, the color purity of the organic light-emitting display device 400 can be further improved.

[0474] A color conversion layer may be included instead of the color filter layer 480 .

[0475] As described above, in the organic light emitting display device 400, the OLEDs D in the red pixels RP, the green pixels GP, and the blue pixels BP emit white light, and the white light from the organic light emitting diodes D passes through the red color filter 482, the green color filter 484, and the blue color filter 486. As a result, red light, green light, and blue light are provided from the red pixels RP, the green pixels GP, and the blue pixels BP, respectively.

[0476] exist Figures 5 to 7 In the present invention, an OLED D emitting white light is used in a display device. Alternatively, for a lighting device, the OLED D can be formed on the entire surface of the substrate without using at least one of a driving element and a color filter layer. A display device and a lighting device each including an OLED D of the present disclosure can be referred to as an organic light-emitting device.

[0477] Figure 8 is a schematic cross-sectional view illustrating an organic light emitting display device according to a third embodiment of the present disclosure.

[0478] like Figure 8As shown, the organic light emitting display device 600 includes a first substrate 610 in which red pixels RP, green pixels GP, and blue pixels BP are defined, a second substrate 670 facing the first substrate 610, an OLED D located between the first substrate 610 and the second substrate 670 and providing white light emission, and a color conversion layer 680 between the OLED D and the second substrate 670.

[0479] Although not shown, color filters may be formed between the second substrate 670 and the respective color conversion layers 680 .

[0480] The first substrate 610 and the second substrate 670 may each be a glass substrate or a flexible substrate. For example, the flexible substrate may be one of a polyimide (PI) substrate, polyethersulfone (PES), polyethylene naphthalate (PEN), polyethylene terephthalate (PET), and polycarbonate (PC).

[0481] TFTs Tr corresponding to respective red, green, and blue pixels RP, GP, and BP are formed on the first substrate 610 , and a passivation layer 650 having a drain contact hole 652 exposing an electrode (eg, drain) of the TFT Tr is formed to cover the TFT Tr.

[0482] The OLED D including the first electrode 660, the organic light emitting layer 662, and the second electrode 664 is formed on the passivation layer 650. In this case, the first electrode 660 may be connected to the drain electrode of the TFT Tr through the drain contact hole 652.

[0483] A bank layer 666 is formed on the passivation layer 650 to cover the edge of the first electrode 660. That is, the bank layer 666 is located at the boundary of the pixel and exposes the center of the first electrode 660 in the pixel. Since the OLED D emits blue light in the red pixel RP, the green pixel GP, and the blue pixel BP, the organic light-emitting layer 662 can be formed as a common layer in the red pixel RP, the green pixel GP, and the blue pixel BP without being separated. The bank layer 666 can be formed to prevent leakage at the edge of the first electrode 660, but it can be omitted.

[0484] OLED D emits blue light and can have Figure 3 or Figure 4 That is, an OLED D is formed in each of the red pixel RP, the green pixel GP, and the blue pixel BP and provides blue light.

[0485] Color conversion layer 680 includes a first color conversion layer 682 corresponding to red pixel RP and a second color conversion layer 684 corresponding to green pixel GP. For example, color conversion layer 680 may include an inorganic color conversion material such as quantum dots. Color conversion layer 680 is not present in blue pixel BP, so that OLED D in the blue pixel can directly face second electrode 664.

[0486] The blue light from the OLED D is converted into red light by the first color conversion layer 682 in the red pixel RP, and the blue light from the OLED D is converted into green light by the second color conversion layer 684 in the green pixel GP.

[0487] Therefore, the organic light emitting display device 600 can display a full-color image.

[0488] On the other hand, when light from the OLED D passes through the first substrate 610 , the color conversion layer 680 is disposed between the OLED D and the first substrate 610 .

[0489] It is obvious to those skilled in the art that various modifications and variations can be made to the embodiments of the present disclosure without departing from the spirit and scope of the present invention. Therefore, it is intended to cover modifications and variations of the present disclosure as long as they are within the scope of the appended claims and their equivalents.

Claims

1. An organic light-emitting device, comprising: substrate; and An organic light emitting diode located on the substrate, the organic light emitting diode comprising: a first electrode; a second electrode facing the first electrode; a first light emitting material layer comprising a first dopant of a boron derivative and a first host of anthracene derivative and located between the first electrode and the second electrode; a first electron blocking layer comprising an electron blocking material and positioned between the first electrode and the first light emitting material layer; and a first hole blocking layer comprising a hole blocking material and located between the second electrode and the first light emitting material layer, Wherein, the first dopant is one of the compounds in Formula 4: [Formula 4] Among them, the first entity is expressed by formula 2: [Formula 2] wherein Ar1 and Ar2 are each independently C6 to C 30 Aryl or C5 to C 30 heteroaryl, and L is a single bond or C6 to C 30 arylene groups, wherein a is an integer from 0 to 8, b, c and d are each independently an integer from 0 to 30, Wherein, at least one of a, b, c and d is a positive integer, Wherein, the electron blocking material is represented by Formula 3: [Formula 3] Among them, in formula 3, R1, R2 and R4 are each independently selected from the group consisting of a monocyclic aryl group or a polycyclic aryl group, R3 is a monocyclic arylene group or a polycyclic arylene group, and at least one of R1, R2, R3 and R4 is polycyclic.

2. The organic light-emitting device according to claim 1, wherein The first host is one of the compounds of Formula 5: [Formula 5] 3. The organic light-emitting device according to claim 1, wherein The electron blocking material is one of the compounds in Formula 6: [Formula 6] 4. The organic light-emitting device according to claim 1, wherein The hole blocking material is represented by Formula 7: [Formula 7] wherein Y1 to Y5 are each independently CR1 or N, and one to three of Y1 to Y5 are N, wherein R1 is independently hydrogen or C6 to C 30 Aryl, Among them, L is C6 to C 30 Arylene, and R2 is C6 to C 50 Aryl or C5 to C 50 heteroaryl, Among them, R3 is C1 to C 10 Alkyl, or two adjacent R3 are connected to form a condensed ring, and wherein a is 0 or 1, b is 1 or 2, and c is an integer from 0 to 4.

5. The organic light emitting device according to claim 4, wherein: The hole blocking material is one of the compounds of Formula 8: [Formula 8] The organic light emitting device according to claim 1 , wherein: The hole blocking material is represented by Formula 9: [Formula 9] Where Ar is C 10 to C 30 arylene, and Among them, R 81 is unsubstituted or substituted with C1 to C 10 Alkyl C6 to C 30 The aryl group may be unsubstituted or substituted with C1 to C 10 Alkyl C5 to C 30 heteroaryl, and Among them, R 82 and R 83 are each independently hydrogen, C1 to C 10 Alkyl or C6 to C 30 Aryl.

7. The organic light emitting device according to claim 6, wherein: The hole blocking material is one of the compounds of formula 9-1: [Formula 9-1] 8. The organic light emitting device according to claim 1, wherein The organic light emitting diode further comprises: a second light-emitting material layer comprising a second dopant of a boron derivative and a second host of anthracene derivative and located between the first light-emitting material layer and the second electrode; and A first charge generation layer is provided between the first light emitting material layer and the second light emitting material layer.

9. The organic light emitting device according to claim 8, wherein: The second dopant is one of the compounds in Formula 4, and the second host is represented by Formula 2.

10. The organic light emitting device according to claim 9, wherein: A red pixel, a green pixel, and a blue pixel are defined on the substrate, and the organic light emitting diode corresponds to each of the red pixel, the green pixel, and the blue pixel, and Wherein, the organic light-emitting device further comprises: The color conversion layer is disposed between the substrate and the organic light emitting diode or on the organic light emitting diode and corresponds to the red pixel and the green pixel.

11. The organic light emitting device according to claim 8, wherein: The organic light emitting diode further comprises: a third light-emitting material layer that emits yellow-green light and is located between the first charge generation layer and the second light-emitting material layer; and A second charge generation layer is provided between the second light emitting material layer and the third light emitting material layer.

12. The organic light emitting device according to claim 8, wherein: The organic light emitting diode further comprises: a third light-emitting material layer that emits red light and green light and is located between the first charge generation layer and the second light-emitting material layer; and A second charge generation layer is provided between the second light emitting material layer and the third light emitting material layer.

13. The organic light emitting device according to claim 8, wherein: The organic light emitting diode further comprises: a third light-emitting material layer including the first layer and the second layer and positioned between the first charge generation layer and the second light-emitting material layer; and a second charge generation layer between the second light emitting material layer and the third light emitting material layer, Among them, the first layer emits red light and the second layer emits yellow-green light.

14. The organic light emitting device according to claim 13, wherein: The third luminescent material layer further includes a third layer that emits green light.

15. The organic light emitting device according to claim 1, wherein The organic light emitting diode further comprises: a second light-emitting material layer that emits yellow-green light and is located between the first light-emitting material layer and the second electrode; and A first charge generation layer is provided between the first light emitting material layer and the second light emitting material layer.

16. The organic light emitting device according to claim 11, wherein: A red pixel, a green pixel, and a blue pixel are defined on the substrate, and the organic light emitting diode corresponds to each of the red pixel, the green pixel, and the blue pixel, and Wherein, the organic light-emitting device further comprises: A color filter layer is disposed between the substrate and the organic light emitting diode or on the organic light emitting diode, and corresponds to the red pixel, the green pixel, and the blue pixel.

17. The organic light emitting device according to claim 1, wherein: A red pixel, a green pixel, and a blue pixel are defined on the substrate, and the organic light emitting diode corresponds to each of the red pixel, the green pixel, and the blue pixel, and Wherein, the organic light-emitting device further comprises: The color conversion layer is disposed between the substrate and the organic light emitting diode or on the organic light emitting diode and corresponds to the red pixel and the green pixel.

18. The organic light emitting device according to claim 1, wherein: The first dopant is one of the compounds of Formula 4-1: [Formula 4-1] 19. The organic light emitting device according to claim 18, wherein: The first host is one of the compounds of formula 5-1: [Formula 5-1] 20. The organic light emitting device according to claim 19, wherein The electron blocking material is one of the compounds in Formula 6-1: [Formula 6-1]

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