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

Abstract

The present disclosure relates to an organic light-emitting diode, comprising: a first electrode; a second electrode facing the first electrode; a first emission portion, comprising a first emission material layer and a hole injection layer and located between the first electrode and the second electrode, wherein the hole injection layer comprises a first hole injection material and a second hole injection material and is located between the first electrode and the first emission material layer, and wherein the first hole injection material is an indacene derivative, and the second hole injection material comprises at least one of fluorene derivatives having different structures.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of Korean Patent Application No. 10-2020-0179673, filed in Korea on December 21, 2020, which is hereby incorporated by reference in its entirety. Technical Field

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

[0004] Currently, the demand for flat panel display devices with a small footprint is increasing. Among flat panel display devices, the technology of organic light emitting display devices including OLEDs is developing rapidly.

[0005] OLEDs emit light by injecting electrons from a cathode serving as an electron injection electrode and holes from an anode serving as a hole injection electrode into an organic emission layer, combining electrons with holes to generate excitons, and converting the excitons from an excited state to a ground state. Flexible transparent substrates, such as plastic substrates, can be used as base substrates for forming elements thereon. In addition, OLEDs can operate at a lower voltage (e.g., 10V or lower) than that required to operate other display devices and have lower power consumption. In addition, the light from OLEDs has excellent color purity.

[0006] The OLED may include a first electrode as an anode, a second electrode facing the first electrode as a cathode, and an organic light emitting layer between the first and second electrodes.

[0007] To improve the light emission efficiency of OLEDs, the organic emission layer may include a hole injection layer (HIL), a hole transport layer (HTL), an emission material layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL) sequentially stacked on a first electrode.

[0008] In an OLED, holes from the first electrode (anode) are transported into the EML through the HIL and HTL, while electrons from the second electrode (cathode) are transported into the EML through the EIL and ETL. The holes and electrons combine in the EML to form excitons, which then transition from an excited state to a ground state, emitting light.

[0009] In order to provide a low driving voltage of an OLED and sufficient luminous efficiency and lifespan, sufficient hole injection efficiency and sufficient hole transport efficiency are required. Summary of the Invention

[0010] Embodiments of the present disclosure are directed to OLEDs and organic light-emitting devices that substantially obviate one or more problems associated with limitations and disadvantages of related conventional technologies.

[0011] Other features and advantages of the present disclosure are set forth in the following description and will be apparent from the description or will be clearly seen through the practice of the present disclosure. The objects and other advantages of the present disclosure are realized and obtained through the features described herein and in the accompanying drawings.

[0012] To achieve these and other advantages according to the purposes of the embodiments of the present disclosure, as described herein, one aspect of the present disclosure is an organic light emitting diode comprising a first electrode; a second electrode facing the first electrode; and a first emission portion, the first emission portion comprising a first emission material layer and a hole injection layer and being located between the first and second electrodes, wherein the hole injection layer comprises a first hole injection material and a second hole injection material and is located between the first electrode and the first emission material layer, wherein the first hole injection material is an organic compound of Formula 1-1: [Formula 1-1] wherein R1 and R2 are each independently selected from hydrogen (H), deuterium (D), halogen, and cyano, wherein R3 to R6 are each independently selected from halogen, cyano, malononitrile, C1-C10 haloalkyl, and C1-C10 haloalkoxy, and at least one of R3 and R4 and at least one of R5 and R6 is malononitrile, wherein X and Y are each independently phenyl substituted with at least one of the following: C1-C10 alkyl, halogen, cyano, malononitrile, C1-C10 haloalkyl, and C1-C10 haloalkoxy, wherein the second hole injection material comprises at least one of the first compound in Formula 2 and the second compound in Formula 3:

[0013] [Formula 2]

[0014] and

[0015] [Formula 3]

[0016] wherein in Formula 2, X1 and X2 are each independently selected from a C6-C30 aryl group and a C5-C30 heteroaryl group, and L1 is selected from a C6-C30 arylene group and a C5-C30 heteroarylene group, wherein a is 0 or 1, wherein each of R1 to R14 is independently selected from H, D, a C1-C10 alkyl group, a C6-C30 aryl group and a C5-C30 heteroaryl group, or adjacent two of R1 to R14 are connected to each other to form a condensed ring; wherein In Formula 3, Y1 and Y2 are each independently selected from a C6-C30 aryl group and a C5-C30 heteroaryl group, L1 is selected from a C6-C30 arylene group and a C5-C30 heteroarylene group, wherein b is 0 or 1, and wherein each of R21 to R34 is independently selected from H, D, a C1-C10 alkyl group, a C6-C30 aryl group and a C5-C30 heteroaryl group, or adjacent two of R21 to R34 are connected to each other to form a condensed ring.

[0017] Another aspect of the present disclosure is an organic light-emitting diode comprising: a first electrode; a second electrode facing the first electrode; a first emission portion comprising a first emission material layer and located between the first and second electrodes; a second emission portion comprising a second emission material layer and located between the first emission portion and the second electrode; and a first p-type charge generation layer comprising a first charge generation material and a second charge generation material and located between the first and second emission portions, wherein the first charge generation material is an organic compound of Formula 1-1: [Formula 1-1] wherein R1 and R2 are each independently selected from hydrogen (H), deuterium (D), halogen, and cyano, wherein R3 to R6 are each independently selected from halogen, cyano, malononitrile, C1-C10 haloalkyl, and C1-C10 haloalkoxy, and at least one of R3 and R4 and at least one of R5 and R6 is malononitrile, wherein X and Y are each independently phenyl substituted with at least one of: C1-C10 alkyl, halogen, cyano, malononitrile, C1-C10 haloalkyl, and C1-C10 haloalkoxy, wherein the second charge generation material comprises at least one of the first compound in Formula 2 and the second compound in Formula 3:

[0018] [Formula 2]

[0019] and

[0020] [Formula 3]

[0021] wherein in Formula 2, X1 and X2 are each independently selected from C6-C30 aryl and C5-C30 heteroaryl, L1 is selected from C6-C30 arylene and C5-C30 heteroarylene, wherein a is 0 or 1, wherein each of R1 to R14 is independently selected from H, D, C1-C10 alkyl, C6-C30 aryl and C5-C30 heteroaryl, or adjacent two of R1 to R14 are connected to each other to form a condensed ring; wherein In Formula 3, Y1 and Y2 are each independently selected from a C6-C30 aryl group and a C5-C30 heteroaryl group, L1 is selected from a C6-C30 arylene group and a C5-C30 heteroarylene group, wherein b is 0 or 1, and wherein each of R21 to R34 is independently selected from H, D, a C1-C10 alkyl group, a C6-C30 aryl group and a C5-C30 heteroaryl group, or adjacent two of R21 to R34 are connected to each other to form a condensed ring.

[0022] Another aspect of the present disclosure is an organic light-emitting device, comprising: a substrate; the organic light-emitting diode described above on the substrate; and an encapsulation film covering the organic light-emitting diode.

[0023] 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

[0024] The accompanying drawings are included to provide a further understanding of the disclosure and are incorporated in and constitute a part of this specification. The drawings illustrate embodiments of the disclosure and together with the description serve to explain the principles of the disclosure.

[0025] Figure 1 is a schematic circuit diagram of an organic light emitting display device disclosed herein.

[0026] Figure 2 is a schematic cross-sectional view of an organic light-emitting device according to a first embodiment of the present disclosure.

[0027] Figure 3 is a schematic cross-sectional view of an OLED according to a second embodiment of the present disclosure.

[0028] Figure 4 is a schematic cross-sectional view of an organic light-emitting device according to a third embodiment of the present disclosure.

[0029] Figure 5 is a schematic cross-sectional view of an OLED according to a fourth embodiment of the present disclosure.

[0030] Figure 6 is a schematic cross-sectional view of an OLED according to a fifth embodiment of the present disclosure. DETAILED DESCRIPTION

[0031] Reference will now be made in detail to some examples and preferred embodiments illustrated in the accompanying drawings.

[0032] The present disclosure relates to OLEDs and organic light-emitting devices including the OLEDs. For example, the organic light-emitting device may be an organic light-emitting display device or an organic light-emitting device. As an example, the organic light-emitting display device will be mainly described, which is a display device including the OLED of the present disclosure.

[0033] Figure 1 is a schematic circuit diagram of an organic light emitting display device disclosed herein.

[0034] like Figure 1 As shown, gate lines GL, data lines DL, and power lines PL are formed in an organic light-emitting display device. The gate lines GL and data lines DL intersect with each other to define pixels (pixels) P. A switching thin film transistor (TFT) Ts, a driving TFT Td, a storage capacitor Cst, and an OLED D are formed in the pixel P. The pixel P may include a red pixel, a green pixel, and a blue pixel. In addition, the pixel P may also include a white pixel.

[0035] A switching thin film transistor Ts is connected to a gate line GL and a data line DL, and 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 a 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 via the switching thin film transistor Ts.

[0036] 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 to the OLED D through the driving thin-film transistor Tr. 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 across the gate electrode of the driving thin-film transistor Td during one frame. As a result, the organic light-emitting display device can display the desired image.

[0037] Figure 2 is a schematic cross-sectional view of an organic light emitting display device according to a first embodiment of the present disclosure.

[0038] like Figure 2As shown. The organic light-emitting display device 100 includes a substrate 110, a TFT Tr, and an OLED D. The OLED D is disposed on a planarization layer 150 and 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 the OLED D may be formed in each of the red, green, and blue pixels. That is, the OLED D emitting red light, green light, and blue light may be disposed in the red, green, and blue pixels, respectively.

[0039] The substrate 110 may be a glass substrate or a flexible substrate. For example, the flexible substrate may be a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylene naphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate, or a polycarbonate (PC) substrate.

[0040] A buffer layer 120 is formed on the substrate, and a TFT Tr is formed on the buffer layer 120. The buffer layer 120 may be omitted.

[0041] A semiconductor layer 122 is formed on the buffer layer 120. The semiconductor layer 122 may include an oxide semiconductor material or polysilicon.

[0042] When the semiconductor layer 122 includes an oxide semiconductor material, a light shielding pattern (not shown) may be formed below the semiconductor layer 122. The light shielding pattern shields or blocks light from reaching the semiconductor layer 122, 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.

[0043] 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.

[0044] A gate electrode 130 formed of a conductive material (eg, metal) is formed on the gate insulating layer 124 to correspond to the center of the semiconductor layer 122 .

[0045] exist Figure 2 In the embodiment, the gate insulating layer 124 is formed on the entire surface of the substrate 110. Alternatively, the gate insulating layer 124 may be patterned to have the same shape as the gate electrode 130.

[0046] 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 such as silicon oxide or silicon nitride or an organic insulating material such as benzocyclobutene or photo-acryl.

[0047] The interlayer insulating layer 132 includes a first contact hole 134 and a second contact hole 136 exposing 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 electrode 130 to be spaced apart from the gate electrode 130.

[0048] The first and second contact holes 134 and 136 are formed through the gate insulating layer 124. Alternatively, when the gate insulating layer 124 is patterned to have the same shape as the gate electrode 130, the first and second contact holes 134 and 136 are formed only through the interlayer insulating layer 132.

[0049] A source electrode 140 and a drain electrode 142 formed of a conductive material (eg, metal) are formed on the interlayer insulating layer 132 .

[0050] The source electrode 140 and the drain electrode 142 are spaced apart from each other with respect to the gate electrode 130 and contact both sides of the semiconductor layer 122 through the first and second contact holes 134 and 136 , respectively.

[0051] 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 ).

[0052] In the TFT Tr, the gate electrode 130, the source electrode 140, and the drain electrode 142 are located on the semiconductor layer 122. That is, the TFT Tr has a coplanar structure.

[0053] 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.

[0054] Although not shown, gate lines and 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.

[0055] In addition, a power supply line 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.

[0056] A 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.

[0057] A first electrode 160 connected to the drain electrode 142 of the TFT Tr through the drain contact hole 152 is formed in each pixel and on the planarization 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 transparent 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).

[0058] 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 transparent 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.

[0059] 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.

[0060] An organic emission layer 162 is formed on the first electrode 160. The organic emission layer 162 includes an emission material layer (EML) including a light-emitting material and a hole injection layer (HIL) below the EML. In addition, the organic emission layer 162 may further include at least one of a hole transport layer (HTL), an electron blocking layer (EBL), a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL).

[0061] As described below, the HIL includes an indacene derivative substituted with a malononitrile group (eg, an indacene compound) as a hole-injection dopant and a fluorene derivative as a hole-injection host, thereby efficiently injecting and / or transporting holes from the anode into the EML.

[0062] A second electrode 164 is formed on the substrate 110 on which the organic emission 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 serve as a cathode. For example, the second electrode 164 can be formed of aluminum (Al), magnesium (Mg), silver (Ag), or alloys thereof (e.g., Al-Mg alloy (AlMg) or Ag-Mg alloy (MgAg)). In the top-emission organic light-emitting display device 100, the second electrode 164 can have a thin profile (small thickness) to provide light transmission characteristics (or semi-transmission characteristics).

[0063] That is, one of the first electrode 160 and the second electrode 164 is a transparent (or semi-transparent) electrode, and the other of the first electrode 160 and the second electrode 164 is a reflective electrode.

[0064] The first electrode 160 , the organic emission layer 162 , and the second electrode 164 constitute an OLED D.

[0065] An encapsulation film 170 is formed on the second electrode 164 to prevent moisture from penetrating into the OLED D. The encapsulation film 170 includes a first inorganic insulating layer 172, an organic insulating layer 174, and a second inorganic insulating layer 176 stacked in sequence, but is not limited thereto. The encapsulation film 170 may be omitted.

[0066] The organic light-emitting display device 100 may further include a color filter layer (not shown). The color filter layer may include a red filter, a green filter, and a blue filter corresponding to red pixels, green pixels, and blue pixels, respectively. The color filter layer may improve the color purity of the organic light-emitting display device 100.

[0067] The organic light-emitting display device 100 may further include a polarizing plate (not shown) to reduce ambient light reflection. For example, the polarizing plate may be a circular polarizing plate. In a bottom-emitting organic light-emitting display device 100, the polarizing plate may be disposed below the substrate 110. In a top-emitting organic light-emitting display device 100, the polarizing plate may be disposed on or above the encapsulation film 170.

[0068] In addition, in the top-emission organic light-emitting display device 100, a cover window (not shown) may be connected to the packaging film 170 or the polarizing plate. In this case, the substrate 110 and the cover window have flexible properties, thereby providing a flexible organic light-emitting display device.

[0069] Figure 3 is a schematic cross-sectional view of an OLED according to a second embodiment.

[0070] like Figure 3 As shown, the OLED D includes a first electrode 160 and a second electrode 164 facing each other, and an organic emission layer 162 located between the first electrode 160 and the second electrode 164. The organic emission layer 162 includes an EML 240 located between the first electrode 160 and the second electrode 164, and a HIL 210 located between the first electrode 160 and the EML 240.

[0071] The first electrode 160 is an anode, and the second electrode 164 is a cathode. One of the first electrode 160 and the second electrode 164 is a transparent electrode (or a semi-transparent electrode), and the other of the first electrode 160 and the second electrode 164 is a reflective electrode.

[0072] Holes are injected and / or transported from the first electrode 160 to the EML 240 through the HIL 210 , and electrons are transported from the second electrode 164 to the EML.

[0073] The organic emission layer 162 may further include an HTL 220 between the HIL 210 and the EML 240. In addition, the organic emission layer 162 may further include at least one of an EIL 260 between the second electrode 164 and the EML 240 and an ETL 250 between the EML 240 and the EIL 260.

[0074] Although not shown, the organic emission layer 162 may further include at least one of an EBL located between the HTL 220 and the EML 240 and an HBL located between the ETL 250 and the EML 240 .

[0075] For example, the HTL 220 may include at least one compound selected from the following group: N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4"-diamine (NPD), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)-benzidine] (polyTPD), poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-diyl)- '-(N-(4-sec-butylphenyl) diphenylamine))] (TFB), di-[4-(N,N-di-p-tolyl-amino)-phenyl] cyclohexane (TAPC), 3,5-bis(9H-carbazol-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, but are not limited thereto. For example, the HTL 220 may include NPD, and its thickness may be Preferred

[0076] The EBL may include at least one compound selected from the group consisting of tris(4-carbazolyl-9-yl-phenyl)amine (TCTA), tris[4-(diethylamino)phenyl]amine, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, TAPC, 4,4',4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 1,3-bis(carbazol-9-yl)benzene (mCP), 3,3'-bis(N- -carbazolyl)-1,1'-biphenyl (mCBP), copper phthalocyanine (CuPc), N,N'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), DCDPA and 2,8-bis(9-phenyl-9H-carbazol-3-yl)dibenzo[b,d]thiophene, but are not limited thereto. The thickness of the EBL can be 2,400 nm. Preferred

[0077] The HBL may include at least one compound selected from the group consisting of tris-(8-hydroxyquinolinolato)aluminum (Alq3), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, lithium hydroxyquinolinolato (Liq), 2,2',2"-(1,3,5-phenyltriyl)-tris(1-phenyl-1-H benzimidazole) (TPBi), bis(2-methyl-8-hydroxyquinolinolato-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthalen-2-yl)4,7-diphenyl-1,10-phenanthroline (NBphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3-(4 The HBL may be, but is not limited to, 1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 1,3,5-tris(p-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), poly[9,9-bis(3'-(((N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene]-alt-2,7-(9,9-dioctylfluorene)] (PFNBr), tris(phenylquinoxaline) (TPQ), and diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1). For example, the thickness of the HBL may be 1,2,4-triazole (TAZ), 1,3,5-tris(p-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), poly[9,9-bis(3'-(((N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene]-alt-2,7-(9,9-dioctylfluorene)] (PFNBr), tris(phenylquinoxaline) (TPQ), and diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1). Preferred

[0078] The ETL 250 may include at least one compound selected from the group consisting of 1,3,5-tris(m-pyridin-3-ylphenyl)benzene (TmPyPB), 2,2',2"-(1,3,5-phenyltriyl)-tris(1-phenyl-1-H benzimidazole) (TPBi), tris(8-hydroxyquinolinolato)aluminum (Alq3), 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 2-biphenyl-4-yl-4,6-bis-(4'-pyridin-2-yl-biphenyl-4-yl)-[1,3,5]triazine (DPT), and bis(2-methyl-8-hydroxyquinolinolato)-4-(phenylphenolate)aluminum (BAlq), but is not limited thereto. For example, the ETL 250 may include an azine-based compound such as TmPyPB, or an imidazole-based compound such as TPBi, and may have a Thickness, preferably

[0079] The EIL 260 may include at least one of an alkali metal (e.g., Li), an alkali halide compound (e.g., LiF, CsF, NaF, or BaF2), and an organic metal compound (e.g., Liq, lithium benzoate, or sodium stearate), but is not limited thereto. For example, the thickness of the EIL 260 may be Preferred

[0080] The EML 240 in the red pixel includes a host and a red dopant, the EML 240 in the green pixel includes a host and a green dopant, and the EML 240 in the blue pixel includes a host and a blue dopant. Each of the red dopant, the green dopant, and the blue dopant can be one of a fluorescent compound, a phosphorescent compound, and a delayed fluorescent compound.

[0081] For example, in the EML 240 in a red pixel, the host may be 4,4'-bis(carbazol-9-yl)-biphenyl (CBP), and the red dopant may be selected from bis(1-phenylisoquinolinolato)iridium acetylacetonate (PIQIr(acac)), bis(1-phenylquinolinolato)iridium acetylacetonate (PQIr(acac)), tris(1-phenylquinolinolato)iridium (PQIr), and platinum octaethylporphyrin (PtOEP). The EML 240 in the red pixel may provide light having a wavelength range (e.g., an emission wavelength range) of approximately 600 to 650 nm.

[0082] In the EML 240 in the green pixel, the host may be CBP, and the green dopant may be face-tris(2-phenylpyridinium)iridium (Ir(ppy)3) or tris(8-hydroxyquinoline)aluminum (Alq3). However, the present invention is not limited thereto. The EML 240 in the green pixel may provide light having a wavelength in the range of approximately 510 to 570 nm.

[0083] In the EML 240 in the blue pixel, the host may be an anthracene derivative and the blue dopant may be a pyrene derivative. However, it is not limited thereto. For example, the host may be 9,10-di(naphthalene-2-yl)anthracene and the blue dopant may be 1,6-bis(diphenylamino)pyrene. In the EML 240 in the blue pixel, the blue dopant may have a weight of 0.1 to 20%, preferably 1 to 10%. The thickness of the EML 240 in the blue pixel may be Preferred And light having a wavelength range of approximately 440 to 480 nm can be provided.

[0084] HIL 210 includes a first hole injection material 212, which is an indacene derivative (e.g., an indacene-based organic compound) substituted with malononitrile, and a second hole injection material 214, which is a fluorene derivative (e.g., a fluorene-based organic compound). The second hole injection material 214 has a highest occupied molecular orbital (HOMO) energy level higher than that of the first hole injection material 212.

[0085] The first hole injection material 212 is represented by Formula 1-1.

[0086] [Formula 1-1]

[0087]

[0088] In Formula 1-1, R1 and R2 are each independently selected from hydrogen (H), deuterium (D), halogen, and cyano. Each of R3 to R6 is independently selected from halogen, cyano, malononitrile, C1-C10 haloalkyl, and C1-C10 haloalkoxy, and at least one of R3 and R4 and at least one of R5 and R6 is malononitrile. X and Y are each independently phenyl substituted with at least one of C1-C10 alkyl, halogen, cyano, malononitrile, C1-C10 haloalkyl, and C1-C10 haloalkoxy.

[0089] For example, the C1-C10 haloalkyl group may be a trifluoromethyl group, and the C1-C10 haloalkoxy group may be a trifluoromethoxy group. In addition, the halogen group may be one of F, Cl, Br, and I.

[0090] In Formula 1-1, one of R3 and R4 and one of R5 and R6 may be malononitrile, and the other of R3 and R4 and the other of R5 and R6 may be a cyano group.

[0091] For example, in Formula 1-1, R3 and R6 may be malononitrile. Alternatively, in Formula 1-1, R4 and R6 may be malononitrile. That is, the first hole injection material 212 in Formula 1-1 may be represented by Formula 1-2 or 1-3.

[0092] [Formula 1-2]

[0093]

[0094] [Formula 1-3]

[0095]

[0096] In Formula 1-1, a substituent at a first side of the indoded nucleus may be different from a substituent at a second side of the indoded nucleus, so that the first hole injection material 212 in Formula 1-1 may have an asymmetric structure.

[0097] For example, each of X and Y may independently be a phenyl group substituted with at least one of a C1-C10 alkyl group, a halogen group, a cyano group, a malononitrile group, a C1-C10 haloalkyl group, and a C1-C10 haloalkoxy group, and X and Y may differ in at least one of the substituents and the position of the substituent. That is, the phenyl moiety that is X and the phenyl moiety that is Y may have different substituents and / or may have the same substituent or different substituents at different positions.

[0098] For example, the first hole injection material 212 in Formula 1-1 may be represented by Formula 1-4.

[0099] [Formula 1-4]

[0100]

[0101] In Formulas 1-4, each of X1 to X3 and each of Y1 to Y3 is independently selected from H, C1-C10 alkyl, halogen, cyano, malononitrile, C1-C10 haloalkyl and C1-C10 haloalkoxy, and satisfies at least one of the following conditions: i) X1 and Y1 are different, ii) X2 is different from Y2 and Y3, or X3 is different from Y2 and Y3.

[0102] The second hole injection material 214 includes at least one of a first compound 216 and a second compound 218, wherein the amine portion (or amino group) of the first compound 216 is directly or through a linker L1 bonded (connected, linked or joined) to the second position of the fluorene portion (or spirofluorene portion), and the amine portion of the second compound 218 is directly or through a linker L1 bonded to the third position of the fluorene portion.

[0103] The HOMO energy level of the first compound 216 is higher than the HOMO energy level of the second compound 218. For example, the HOMO energy level of the first compound 216 may be equal to or higher than -5.50 eV, and the HOMO energy level of the second compound 218 may be lower than -5.50 eV. The difference between the HOMO energy levels of the first compound 216 and the second compound 218 may be 0.3 eV or less.

[0104] The first compound 216 is represented by Formula 2.

[0105] [Formula 2]

[0106]

[0107] In Formula 2, X1 and X2 are each independently selected from a C6-C30 aryl group and a C5-C30 heteroaryl group, L1 is selected from a C6-C30 arylene group and a C5-C30 heteroarylene group, and a is 0 or 1. Each of R1 to R14 is independently selected from H, D, a C1-C10 alkyl group, a C6-C30 aryl group, and a C5-C30 heteroaryl group, or adjacent two of R1 to R14 are connected (bound or joined) to each other to form a fused ring.

[0108] In the above formula 2 and the following formula 3, the C6 to C30 aryl (or arylene) group may be selected from: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, pentanenyl, indenyl, indenoindenyl, heptalenyl, biphenylenyl, indacenyl, phenanthrenyl, triphenylenyl, dibenzophenanthrenyl, azulenyl, pyrenyl, fluoranthenyl, triphenylenyl, phenyl, tetraphenyl, tetrasenyl, fluorenyl, pentaphenyl, pentacenyl, fluorenyl, indenofluorenyl and spirofluorenyl.

[0109] In the above formula 2 and the following formula 3, the C5-C30 heteroaryl (or heteroarylene) can be selected from: pyrrolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, imidazolyl, pyrazolyl, indolyl, isoindolyl, indazolyl, indolizinyl, pyrrolizinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolecarbazolyl, indenocarbazolyl, benzofurancarbazolyl, benzothiophenecarbazolyl, quinolyl, isoquinolyl, phthalazinyl, quinoxalinyl, cinnolinyl, quinazolinyl, quinozolinyl, quinolyl, purinyl, phthalazinyl, quinoxalinyl, benzoquinolyl, benzoisoquinolyl, benzoquinazolinyl, benzoquinoxalinyl, acridinyl, phenanthrolinyl, perimidinyl, phenanthridinyl, pteridinyl, cinnolinyl, naphthyridinyl, furanyl, oxazinyl, oxazolyl, oxadiazolyl, triazolyl, dioxynyl, benzofuranyl, dibenzofuranyl, thiopyranyl, xantenyl, chromanyl, isochromanyl, thioazinyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, difuryrazinyl, benzofurandibenzofuranyl, benzothiophenebenzothiophenyl, benzothiophenedibenzothiophenyl, benzothiophenebenzofuranyl, and benzothiophenedibenzofuranyl.

[0110] In the above formula 2 and the following formula 3, each of the C6-C30 aryl group and the C5-C30 heteroaryl group may include substituted and unsubstituted groups. That is, each of the C6-C30 aryl group and the C5-C30 heteroaryl group may be unsubstituted or substituted with a C1-C10 alkyl group (e.g., a methyl group, an ethyl group, or a tert-butyl group).

[0111] In Formula 2, X1 and X2 may be the same or different. Each of X1 and X2 may be selected from a fluorenyl group, a spirofluorenyl group, a phenyl group, a biphenyl group, a tert-butylphenyl group, a fluorenylphenyl group, a carbazolyl group, and a carbazolylphenyl group, and L1 may be a phenylene group. Each of R1 to R14 may be selected from H, D, a C1-C10 alkyl group (e.g., a tert-butyl group), and a C6-C30 aryl group (e.g., a phenyl group), and two adjacent groups of R1 to R14 (e.g., R1 and R6) may be connected to form a condensed ring. The condensed ring may be one of an aromatic ring, an alicyclic ring, and a heteroaromatic ring.

[0112] The second compound 218 is represented by Formula 3.

[0113] [Formula 3]

[0114]

[0115] In Formula 3, Y1 and Y2 are each independently selected from a C6-C30 aryl group and a C5-C30 heteroaryl group, L1 is selected from a C6-C30 arylene group and a C5-C30 heteroarylene group, and b is 0 or 1. Each of R21 to R34 is independently selected from H, D, a C1-C10 alkyl group, a C6-C30 aryl group, and a C5-C30 heteroaryl group, or adjacent two of R21 to R34 are connected (bound or joined) to each other to form a condensed ring.

[0116] In Formula 3, Y1 and Y2 may be the same or different. Each of Y1 and Y2 may be selected from fluorenyl, spirofluorenyl, phenyl, biphenyl, tert-butylphenyl, fluorenylphenyl, carbazolyl, and carbazolylphenyl, and L1 may be a phenylene group. Each of R21 to R34 may be selected from H, D, a C1-C10 alkyl group (e.g., a tert-butyl group), and a C6-C30 aryl group (e.g., a phenyl group), and adjacent two of R21 to R34 (e.g., R21 and R26) may be connected to form a condensed ring. The condensed ring may be one of an aromatic ring, an alicyclic ring, and a heteroaromatic ring.

[0117] In the HIL 210, the weight percentage of the first hole injection material 212 may be less than the weight percentage of the second hole injection material 214. That is, in the HIL 210, the second hole injection material 214 may be referred to as a host, and the first hole injection material 212 may be referred to as a dopant. For example, in the HIL 210, the first hole injection material 212 may have an amount of approximately 1 to 25 weight percent, and the second hole injection material 214 may have an amount of approximately 75 to 99 weight percent.

[0118] In the OLED D of the present disclosure, the HIL 210 includes a first hole injection material 212, which may be a host, and at least one of first and second compounds 216 and 218, each of which may be a dopant, so that the HIL 210 has excellent hole injection performance. Therefore, the hole injection efficiency from the first electrode 160, which is an anode, is improved.

[0119] More specifically, hole injection performance from the first electrode 160 is improved by the first compound 216 having a high HOMO energy level, and a potential barrier between the HIL 210 and the HTL 220 is lowered by the second compound 218 having a low HOMO energy level.

[0120] When the HIL 210 includes all of the first hole injection material 212, the first compound 216, and the second compound 218, the weight percentage of the first hole injection material 212 may be less than the weight percentage of each of the first and second compounds 216 and 218. Furthermore, the weight percentage of the first compound 216 may be equal to or greater than the weight percentage of the second compound 218. For example, the weight percentage ratio of the first compound 216 to the second compound 218 may be approximately 5:5 to 6:4. When the weight percentage of the first compound 216 is less than the weight percentage range of the present disclosure, hole injection performance from the first electrode 160 is reduced. When the weight percentage of the first compound 216 is greater than the weight percentage range of the present disclosure, the potential barrier between adjacent layers (e.g., the HIL 210 and the HTL 220) increases, thereby reducing hole transport performance.

[0121] The first hole injection material 212 in Formula 1-1 may be one of the compounds in Formula 4.

[0122] [Formula 4]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129] The first compound 216 in Formula 2 may be one of the compounds in Formula 5.

[0130] [Formula 5]

[0131]

[0132]

[0133]

[0134] The second compound 218 in Formula 3 may be one of the compounds in Formula 6.

[0135] [Formula 6]

[0136]

[0137]

[0138] [synthesis]

[0139] 1. Synthesis of Compound A04

[0140] (1) Compound 4-A

[0141] [Reaction formula 1-1]

[0142]

[0143] 2,2'-(4,6-dibromo-1,3-phenylene)diacetonitrile (180g, 573mmol), toluene (6L), copper iodide (CuI, 44mmol), tetrakis(triphenylphosphine)palladium (44mmol), diisopropylamine (2885mmol) and 1-ethynyl-4-(trifluoromethyl)benzene (637mmol) were mixed and heated to 100°C. After the reaction, the solvent (5L) was distilled off. The mixture was cooled to room temperature and filtered to obtain a solid. After the solid was dissolved in chloroform and extracted with water, magnesium sulfate and acidic clay were added and stirred for 1 hour. The mixture was filtered and the solvent was distilled again. The mixture was recrystallized from ethanol to obtain compound 4-A (104g). (Yield 45%, MS [M+H] + = 403)

[0144] (2) Compound 4-B

[0145] [Reaction formula 1-2]

[0146]

[0147] Compound 4-A (104 g, 258 mmol), toluene (3 L), CuI (21 mmol), tetrakis(triphenylphosphine)palladium (21 mmol), diisopropylamine (1290 mmol), and 1-ethynyl-4-(trifluoromethoxy)benzene (258 mmol) were mixed, heated to 100°C, and stirred for 2 hours. After the reaction, the solvent (2 L) was distilled off. The mixture was cooled to room temperature and filtered to obtain a solid. The solid was dissolved in chloroform and extracted with water, followed by addition of magnesium sulfate and acidic clay and stirring for 1 hour. After filtering the mixture, the solvent was distilled again. The mixture was recrystallized from tetrahydrofuran and ethanol to obtain compound 4-B (39.3 g). (Yield 30%, MS [M+H] + = 509).

[0148] (3) Compound 4-C

[0149] [Reaction formula 1-3]

[0150]

[0151] Compound 4-B (39 g, 77 mmol), 1,4-dioxane (520 mL), diphenyl sulfoxide (462 mmol), copper (II) bromide (CuBr (II), 15 mmol), and palladium acetate (15 mmol) were mixed, heated to 100°C, and stirred for 5 hours. After the reaction, the solvent was distilled off. The mixture was dissolved in chloroform, acidic clay was added and stirred for 1 hour. After filtering the mixture, the solvent was distilled again. The mixture was reverse precipitated with hexane to obtain a solid. The solid was recrystallized with tetrahydrofuran and hexane, and filtered to obtain compound 4-C (7 g). (Yield 17%, MS [M+H] + = 537)

[0152] (4) Compound A04

[0153] [Reaction formula 1-4]

[0154]

[0155] Compound 4-C (7 g, 13 mmol), dichloromethane (220 mL) and malononitrile (96 mmol) were added and cooled to 0 ° C. Titanium (IV) chloride (65 mmol) was slowly added and stirred at 0 ° C for 1 hour. Pyridine (97.5 mmol) dissolved in dichloromethane (75 mL) was slowly added to the mixture at 0 ° C and stirred for 1 hour. After the reaction was completed, acetic acid (130 mmol) was added and stirred for another 30 minutes. After the reaction solution was extracted with water, the organic layer was reversely precipitated in hexane to obtain a solid. After the solid was filtered through acetonitrile, magnesium sulfate and acidic clay were added and stirred for 30 minutes. After filtering the solution, it was recrystallized from acetonitrile and toluene and washed with toluene. The solid was recrystallized from acetonitrile and tert-butyl methyl ether and purified by sublimation to obtain compound A04 (1.6 g). (Yield 20%, MS [M + H] + = 633)

[0156] 2. Synthesis of Compound A13

[0157] (1) Compound 13-A

[0158] [Reaction formula 2-1]

[0159]

[0160] 2,2'-(4,6-dibromo-1,3-phenylene)diacetonitrile (200g, 637mmol), toluene (6L), copper iodide (CuI, 51mmol), tetrakis(triphenylphosphine)palladium (51mmol), diisopropylamine (3185mmol) and 1-ethynyl-3,5-bis(trifluoromethyl)benzene (637mmol) were mixed and heated to 100°C. After the reaction, the solvent (5L) was distilled off. The mixture was cooled to room temperature and filtered to obtain a solid. After the solid was dissolved in chloroform and extracted with water, magnesium sulfate and acidic clay were added and stirred for 1 hour. The mixture was filtered and the solvent was distilled again. The mixture was recrystallized from ethanol to obtain compound 13-A (105g). (Yield 35%, MS [M+H] + = 471)

[0161] (2) Compound 13-B

[0162] [Reaction formula 2-2]

[0163]

[0164] Compound 13-A (105 g, 223 mmol), toluene (3 L), CuI (18 mmol), tetrakis(triphenylphosphine)palladium (18 mmol), diisopropylamine (1115 mmol) and 4-ethynyl-2-(trifluoromethyl)benzonitrile (223 mmol) were mixed, heated to 100° C., and stirred for 2 hours. After the reaction, the solvent (2 L) was distilled off. The mixture was cooled to room temperature and filtered to obtain a solid. The solid was dissolved in chloroform and extracted with water, and then magnesium sulfate and acidic clay were added and stirred for 1 hour. After filtering the mixture, the solvent was distilled again. The mixture was recrystallized from tetrahydrofuran and ethanol to obtain compound 13-B (32.6 g). (Yield 25%, MS [M+H] + = 586)

[0165] (3) Compound 13-C

[0166] [Reaction formula 2-3]

[0167]

[0168] Compound 13-B (32 g, 55 mmol), 1,4-dioxane (480 mL), diphenyl sulfoxide (330 mmol), CuBr(II) (11 mmol), and palladium acetate (11 mmol) were mixed, heated to 100°C, and stirred for 5 hours. After the reaction, the solvent was distilled off. The mixture was dissolved in chloroform, acidic clay was added, and stirred for 1 hour. After filtering the mixture, the solvent was distilled again. The mixture was reverse precipitated with hexane to obtain a solid. The solid was recrystallized with tetrahydrofuran and hexane, and filtered to obtain compound 13-C (5 g). (Yield 15%, MS [M+H] + = 614)

[0169] (4) Compound A13

[0170] [Reaction formula 2-4]

[0171]

[0172] Compound 13-C (5 g, 8.2 mmol), dichloromethane (150 mL) and malononitrile (49.2 mmol) were added and cooled to 0°C. Titanium (IV) chloride (41 mmol) was slowly added and stirred at 0°C for 1 hour. Pyridine (61.5 mmol) dissolved in dichloromethane (50 mL) was slowly added to the mixture at 0°C and stirred for 1 hour. After the reaction was completed, acetic acid (82 mmol) was added and stirred for another 30 minutes. After the reaction solution was extracted with water, the organic layer was reversely precipitated in hexane to obtain a solid. After the solid was filtered through acetonitrile, magnesium sulfate and acidic clay were added and stirred for 30 minutes. After the solution was filtered, it was recrystallized from acetonitrile and toluene and washed with toluene. The solid was recrystallized from acetonitrile and tert-butyl methyl ether and purified by sublimation to obtain compound A13 (1 g). (Yield 18%, MS [M+H] + = 710)

[0173] 3. Synthesis of Compound A37

[0174] (1) Compound 37-A

[0175] [Reaction formula 3-1]

[0176]

[0177] 2,2'-(4,6-dibromo-2-fluoro-1,3-phenylene)diacetonitrile (300g, 903.7mmol), toluene (9L), CuI (72.3mmol), tetrakis(triphenylphosphine)palladium (72.3mmol), diisopropylamine (4518mmol) and 1-ethynyl-3,5-bis(trifluoromethyl)benzene (903.7mmol) were mixed and heated to 100°C. After the reaction, the solvent (8L) was distilled off. The mixture was cooled to room temperature and filtered to obtain a solid. After the solid was dissolved in chloroform and extracted with water, magnesium sulfate and acidic clay were added and stirred for 1 hour. The mixture was filtered and the solvent was distilled again. The mixture was recrystallized from ethanol to obtain compound 37-A (137g). (Yield 31%, MS [M+H] + = 489)

[0178] (2) Compound 37-B

[0179] [Reaction formula 3-2]

[0180]

[0181] Compound 37-A (137 g, 280 mmol), toluene (4.1 L), CuI (22 mmol), tetrakis(triphenylphosphine)palladium (22 mmol), diisopropylamine (1400 mmol) and 4-ethynyl-2-(trifluoromethyl)benzonitrile (280 mmol) were mixed, heated to 100° C., and stirred for 2 hours. After the reaction, the solvent (3 L) was distilled off. The mixture was cooled to room temperature and filtered to obtain a solid. The solid was dissolved in chloroform and extracted with water, and then magnesium sulfate and acidic clay were added and stirred for 1 hour. After filtering the mixture, the solvent was distilled again. The mixture was recrystallized from tetrahydrofuran and ethanol to obtain compound 37-B (33.8 g). (Yield 20%, MS [M+H] + = 603)

[0182] (3) Compound 37-C

[0183] [Reaction formula 3-3]

[0184]

[0185] Compound 37-B (33 g, 54.7 mmol), 1,4-dioxane (500 mL), diphenyl sulfoxide (328.2 mmol), CuBr(II) (10.9 mmol), and palladium acetate (10.9 mmol) were mixed, heated to 100° C., and stirred for 5 hours. After the reaction, the solvent was distilled off. The mixture was dissolved in chloroform, acidic clay was added, and stirred for 1 hour. After filtering the mixture, the solvent was distilled again. The mixture was reverse precipitated with hexane to obtain a solid. The solid was recrystallized with tetrahydrofuran and hexane, and filtered to obtain compound 37-C (4.8 g). (Yield 14%, MS [M+H] + = 632)

[0186] (4) Compound 37

[0187] [Reaction formula 3-4]

[0188]

[0189] Compound 37-C (4.8 g, 7.6 mmol), dichloromethane (145 mL) and malononitrile (45.6 mmol) were added and cooled to 0°C. Titanium (IV) chloride (38 mmol) was slowly added and stirred at 0°C for 1 hour. Pyridine (57 mmol) dissolved in dichloromethane (48 mL) was slowly added to the mixture at 0°C and stirred for 1 hour. After the reaction was completed, acetic acid (76 mmol) was added and stirred for another 30 minutes. After the reaction solution was extracted with water, the organic layer was reversely precipitated in hexane to obtain a solid. After the solid was filtered through acetonitrile, magnesium sulfate and acidic clay were added and stirred for 30 minutes. After the solution was filtered, it was recrystallized from acetonitrile and toluene, and then washed with toluene. The solid was recrystallized from acetonitrile and tert-butyl methyl ether and purified by sublimation to obtain compound A37 (1.1 g). (Yield 20%, MS [M+H] + = 728)

[0190] As described above, in the OLED D of the present disclosure, the HIL 210 includes a first hole injection material 212 and a second hole injection material 214. The first hole injection material 212 is an organic compound of Formula 1-1, and the second hole injection material 214 includes at least one of a first compound 216, an organic compound of Formula 2, and a second compound 218, an organic compound of Formula 3. This allows holes to be efficiently injected and / or transported from the first electrode 160 to the EML 240. Therefore, the driving voltage of the OLED D is reduced, and the luminous efficiency and lifespan of the OLED D are improved.

[0191] Figure 4 is a schematic cross-sectional view of an organic light-emitting device according to a third embodiment of the present disclosure. Figure 5 is a schematic cross-sectional view of an OLED according to a fourth embodiment of the present disclosure, and Figure 6 is a schematic cross-sectional view of an OLED according to a fifth embodiment of the present disclosure.

[0192] like Figure 4 As shown, the organic light-emitting display device 300 includes: a first substrate 310 in which red pixels BP, green pixels GP and blue pixels BP are defined; a second substrate 370 facing the first substrate 310; an OLED D located between the first substrate 310 and the second substrate 370 and providing white light emission, and a color filter layer 380 located between the OLED D and the second substrate 370.

[0193] Each of the first substrate 310 and the second substrate 370 may be a glass substrate or a flexible substrate. For example, each of the first substrate 310 and the second substrate 370 may be a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylene naphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate, or a polycarbonate (PC) substrate.

[0194] A buffer layer 320 is formed on the substrate, and a TFT Tr corresponding to each of the red, green, and blue pixels RP, GP, and BP is formed on the buffer layer 320. The buffer layer 320 may be omitted.

[0195] A semiconductor layer 322 is formed on the buffer layer 320. The semiconductor layer 322 may include an oxide semiconductor material or polysilicon.

[0196] A gate insulating layer 324 is formed on the semiconductor layer 322. The gate insulating layer 324 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride.

[0197] A gate electrode 330 formed of a conductive material (eg, metal) is formed on the gate insulating layer 324 to correspond to the center of the semiconductor layer 322 .

[0198] An interlayer insulating layer 332 formed of an insulating material is formed on the gate electrode 330. The interlayer insulating layer 332 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride or an organic insulating material such as benzocyclobutene or photopropylene.

[0199] The interlayer insulating layer 332 includes a first contact hole 334 and a second contact hole 336 exposing both sides of the semiconductor layer 322. The first contact hole 334 and the second contact hole 336 are located on both sides of the gate electrode 330 to be spaced apart from the gate electrode 330.

[0200] A source electrode 340 and a drain electrode 342 formed of a conductive material (eg, metal) are formed on the interlayer insulating layer 332 .

[0201] The source electrode 340 and the drain electrode 342 are spaced apart from each other with respect to the gate electrode 330 , and contact both sides of the semiconductor layer 322 through the first contact hole 334 and the second contact hole 336 , respectively.

[0202] The semiconductor layer 322, the gate electrode 330, the source electrode 340, and the drain electrode 342 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 ).

[0203] Although not shown, gate lines and 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.

[0204] In addition, a power supply line 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.

[0205] The planarization layer 350 is formed to cover the TFT Tr, and includes a drain contact hole 352 exposing the drain electrode 342 of the TFT Tr.

[0206] A first electrode 360 ​​connected to the drain electrode 342 of the TFT Tr through the drain contact hole 352 is formed in each pixel and on the planarization layer 350. The first electrode 360 ​​may be an anode and may be formed of a conductive material having a relatively high work function, such as a transparent conductive oxide (TCO). The first electrode 360 ​​may further include a reflective electrode or a reflective layer. For example, the reflective electrode or the reflective layer may be formed of silver (Ag) or an aluminum-palladium-copper (APC) alloy. In the top-emission organic light-emitting display device 300, the first electrode 360 ​​may have a three-layer structure of ITO / Ag / ITO or ITO / APC / ITO.

[0207] A bank layer 366 is formed on the planarization layer 350 to cover the edges of the first electrode 360. That is, the bank layer 366 is located at the boundary of the pixel and exposes the center of the first electrode 360 ​​in the pixel. Since the OLED D emits white light in the red, green, and blue pixels RP, GP, and BP, the organic emission layer 162 can be formed as a common layer in the red, green, and blue pixels RP, GP, and BP without being separated. The bank layer 366 can be formed to prevent current leakage at the edge of the first electrode 360, and the bank layer 366 can be omitted.

[0208] An organic emission layer 362 is formed on the first electrode 360 ​​.

[0209] refer to Figure 5 The organic emission layer 362 includes a first emission portion 410, a second emission portion 430, and a charge generation layer (CGL) 450 located between the first emission portion 410 and the second emission portion 430, wherein the first emission portion 410 includes a first EML 416 and a HIL 420, and the second emission portion 430 includes a second EML 434.

[0210] The CGL 450 is located between the first emission portion 410 and the second emission portion 430, and the first emission portion 410, the CGL 450, and the second emission portion 430 are sequentially stacked on the first electrode 360. That is, the first emission portion 410 is located between the first electrode 360 ​​and the CGL 450, and the second emission portion 430 is located between the second electrode 364 and the CGL 450.

[0211] In the first emission portion 410, the HIL 420 is located under the first EML 416. That is, the HIL 420 is located between the first electrode 360 ​​and the first EML 416.

[0212] The first transmitting portion 410 may further include at least one of a first HTL 414 located between the HIL 420 and the first EML 416 and a first ETL 418 located above the first EML 416 .

[0213] Although not shown, the first transmitting portion 410 may further include at least one of an EBL between the first HTL 414 and the first EML 416 and an HBL between the first EML 416 and the first ETL 418 .

[0214] The second emission portion 430 may further include at least one EIL 436 above the second EML 434. In addition, the second emission portion 430 may further include at least one of a second HTL 432 below the second EML 434 and a second ETL 440 between the second EML 434 and the EIL 436.

[0215] Although not shown, the second transmitting portion 430 may further include at least one of an EBL located between the second HTL 432 and the second EML 434 and an HBL located between the second EML 434 and the second ETL 440 .

[0216] One of the first EML 416 and the second EML 434 provides light having a wavelength range of approximately 440 to 480 nm, and the other of the first EML 416 and the second EML 434 provides light having a wavelength range of approximately 500 to 550 nm. For example, the first EML 416 may provide light having a wavelength range of approximately 440 to 480 nm, and the second EML 434 may provide light having a wavelength range of approximately 500 to 550 nm. Alternatively, the second EML 434 may have a double-layer structure with a first layer emitting red light and a second layer emitting green light. In this case, the first layer emitting red light may include a host and a red dopant, and the second layer emitting green light may include a host and a green dopant.

[0217] In the first EML 416 having a wavelength range of 440 to 480 nm, the host may be an anthracene derivative, and the dopant may be a pyrene derivative. For example, in the first EML 416, the host may be 9,10-di(naphthalene-2-yl)anthracene, and the dopant may be 1,6-bis(diphenylamino)pyrene. In the second EML 434 having a wavelength range of 500 to 550 nm, the host may be a carbazole derivative, and the dopant may be an iridium derivative (complex). For example, in the second EML 434, the host may be 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), and the dopant may be tris(2-phenylpyridine)iridium(III) (Ir(ppy)3).

[0218] The CGL 450 includes an n-type CGL 452 and a p-type CGL 454. The n-type CGL 452 is located between the first ETL 418 and the second HTL 432, and the p-type CGL 454 is located between the n-type CGL 452 and the second HTL 432.

[0219] The n-type CGL 452 supplies electrons to the first ETL 418, and the electrons are transferred to the first EML 416 through the first ETL 418. The p-type CGL 454 supplies holes to the second HTL 432, and the holes are transferred to the second EML 434 through the second HTL 432. Therefore, in the OLED D having a two-stack (double-stack) structure, the driving voltage is reduced and the emission efficiency is improved.

[0220] The n-type CGL 452 includes an n-type charge generating material and may have a thickness of 100 to 100 nm. For example, the n-type charge generating material may be selected from the group consisting of tris-(8-hydroxyquinoline)aluminum (Alq3), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, hydroxyquinoline lithium (Liq), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthalene-2-yl)4,7-diphenyl-1,10-phenanthroline (NBphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2 ,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 1,3,5-tris(p-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), poly[9,9-bis(3'-(((N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene]-alt-2,7-(9,9-dioctylfluorene)] (PFNBr), tris(phenylquinoxaline) (TPQ) and diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1). In one embodiment of the present disclosure, the n-type charge generating material may be a phenanthroline derivative, for example, bathophenanthroline (Bphen).

[0221] Additionally, the n-type CGL 452 may further include an auxiliary n-type charge generation material. For example, the auxiliary n-type charge generation material may be an alkali metal such as Li, Cs, K, Rb, Na, or Fr, or an alkaline earth metal such as Be, Mg, Ca, Sr, Ba, or Ra. The auxiliary n-type charge generation material may comprise approximately 0.1 to 20% by weight of the n-type CGL 452, preferably approximately 1 to 10% by weight.

[0222] At least one of the HIL 420 and the p-type CGL 454 includes at least one of the organic compound of Formula 1-1, the organic compound of Formula 2, and the organic compound of Formula 3. For example, the HIL 420 may include a first hole injection material 422 and a second hole injection material 424. In this case, the first hole injection material 422 is the organic compound of Formula 1-1, and the second hole injection material 424 includes at least one of a first compound 426 that is the organic compound of Formula 2 and a second compound 428 that is the organic compound of Formula 3. The p-type CGL 454 may include a first p-type charge generation material 456 and a second p-type charge generation material 457. In this case, the first p-type charge generation material 456 is the organic compound of Formula 1-1, and the second p-type charge generation material 457 includes at least one of a third compound 458 that is the organic compound of Formula 2 and a fourth compound 459 that is the organic compound of Formula 3.

[0223] The first hole injection material 422 in the HIL 420 and the first p-type charge generation material 456 in the p-type CGL 454 may be the same or different. Each of the first compound 426 and the second compound 428 in the HIL 420 and each of the third compound 458 and the fourth compound 459 in the p-type CGL 454 may be the same or different.

[0224] In the HIL 420, the weight percentage of the first hole injection material 422 may be less than the weight percentage of the second hole injection material 424. That is, in the HIL 420, the second hole injection material 424 may be referred to as a host, and the first hole injection material 422 may be referred to as a dopant. For example, in the HIL 420, the first hole injection material 422 may have approximately 1 to 25 weight percent, and the second hole injection material 424 may have approximately 75 to 99 weight percent.

[0225] When the HIL 420 includes all of the first hole injection material 422, the first compound 426, and the second compound 428, the weight percentage of the first hole injection material 422 may be less than the weight percentage of each of the first compound 426 and the second compound 428. In addition, the weight percentage of the first compound 426 may be equal to or greater than the weight percentage of the second compound 428. For example, the weight percentage ratio of the first compound 426 to the second compound 428 may be about 5:5 to 6:4. The HIL 420 may have a thickness of about 50 to 60 mm. thickness.

[0226] In the p-type CGL 454, the weight percentage of the first p-type charge generation material 456 may be less than the weight percentage of the second p-type charge generation material 457. That is, in the p-type CGL 454, the second p-type charge generation material 457 may be referred to as a host, and the first p-type charge generation material 456 may be referred to as a dopant. For example, in the p-type CGL 454, the first p-type charge generation material 456 may have a weight percentage of approximately 1 to 25%, and the second p-type charge generation material 457 may have a weight percentage of approximately 75 to 99%.

[0227] When the p-type CGL 454 includes all of the first p-type charge generation material 456, the third compound 458, and the fourth compound 459, the weight percentage of the first p-type charge generation material 456 may be less than the weight percentage of each of the third compound 458 and the fourth compound 459. In addition, the weight percentage of the third compound 458 may be equal to or greater than the weight percentage of the fourth compound 459. For example, the weight percentage ratio of the third compound 458 to the fourth compound 459 may be about 5:5 to 6:4. The p-type CGL 454 may have a thickness of about 100 to about 100 mm. thickness.

[0228] When the HIL 420 includes the first hole injection material 422, the first compound 426, and the second compound 428, and the p-type CGL 454 includes the first p-type charge generation material 456, the third compound 458, and the fourth compound 459, a weight percentage ratio of the first compound 426 to the second compound 428 in the HIL 420 may be smaller than a weight percentage ratio of the third compound 458 to the fourth compound 459 in the p-type CGL 454. For example, the first compound 426 and the second compound 428 may have the same weight percentage in the HIL 420, and a weight percentage of the third compound 458 may be greater than a weight percentage of the fourth compound 459 in the p-type CGL 454.

[0229] As described above, the first compound 426 and the third compound 458, which are organic compounds of Formula 2, have relatively high HOMO energy levels and excellent hole injection performance. HIL 420 can be used to inject holes from first electrode 360, which serves as an anode, into first HTL 414, and p-type CGL 454 can be used to directly inject holes into second emission portion 430. Therefore, the ratio of third compound 458, which is an organic compound of Formula 2, in p-type CGL 454 is relatively high, thereby further improving the hole injection performance of p-type CGL 454.

[0230] For example, when the HIL 420 and the p-type CGL 454 include a first hole injection material 422 that is an organic compound in Formula 1-1 and a first p-type charge generation material 456 that is an organic compound in Formula 1-1, respectively, the weight percentage of the first p-type charge generation material 456 in the p-type CGL 454 may be equal to or greater than the weight percentage of the first hole injection material 422 in the HIL 420.

[0231] The OLED D includes a first emission portion 410 having a wavelength range of 440 to 480 nm and a second emission portion 430 having a wavelength range of 500 to 550 nm, and provides white light emission, with a CGL 450 including a first p-type charge generation material 456 and a second p-type charge generation material 457 disposed between the first emission portion 410 and the second emission portion 430. Therefore, the OLED D has advantages in terms of driving voltage, emission efficiency, and lifespan.

[0232] refer to Figure 6 The organic emission layer 362 includes: a first emission portion 510 including a first EML 516 and a HIL 520, a second emission portion 530 including a second EML 534, a third emission portion 550 including a third EML 554, and a first CGL 570 located between the first emission portion 510 and the second emission portion 530 and a second CGL 580 located between the second emission portion 530 and the third emission portion 550.

[0233] The first CGL 570 is located between the first emission portion 510 and the second emission portion 530, and the second CGL 580 is located between the second emission portion 530 and the third emission portion 550. That is, the first emission portion 510, the first CGL 570, the second emission portion 530, the second CGL 580, and the third emission portion 550 are sequentially stacked on the first electrode 360. In other words, the first emission portion 510 is located between the first electrode 360 ​​and the first CGL 570, the second emission portion 530 is located between the first CGL 570 and the second CGL 580, and the third emission portion 550 is located between the second electrode 364 and the second CGL 580.

[0234] In the first emission portion 510, the HIL 520 is located under the first EML 516. That is, the HIL 520 is located between the first electrode 360 ​​and the first EML 516.

[0235] The first transmitting portion 510 may further include at least one of a first HTL 514 located between the HIL 520 and the first EML 516 and a first ETL 518 located above the first EML 516 .

[0236] Although not shown, the first transmitting portion 510 may further include at least one of an EBL located between the first HTL 514 and the first EML 516 and an HBL located between the first EML 516 and the first ETL 518 .

[0237] The second emission portion 530 may further include at least one of a second HTL 532 below the second EML 534 and a second ETL 540 above the second EML 534 .

[0238] Although not shown, the second transmitting portion 530 may further include at least one of an EBL located between the second HTL 532 and the second EML 534 and an HBL located between the second EML 534 and the second ETL 540 .

[0239] The third emission part 550 may further include an EIL 556. In addition, the third emission part 550 may further include at least one of a third HTL 552 below the third EML 554 and a third ETL 560 between the third EML 554 and the EIL 556.

[0240] Although not shown, the third transmitting portion 550 may further include at least one of an EBL located between the third HTL 552 and the third EML 554 and an HBL located between the third EML 554 and the third ETL 560 .

[0241] Each of the first EML 516 and the third EML 554 provides light having a wavelength range of approximately 440 to 480 nm, and the second EML 534 provides light having a wavelength range of approximately 500 to 550 nm. Alternatively, the second EML 534 may have a double-layer structure with a first layer emitting red light and a second layer emitting green light. Furthermore, the second EML 534 may have a triple-layer structure: 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.

[0242] In each of the first EML 516 and the third EML 554, the host may be an anthracene derivative, and the dopant may be a pyrene derivative. For example, in each of the first EML 516 and the third EML 554, the host may be 9,10-di(naphthalene-2-yl)anthracene, and the dopant may be 1,6-bis(diphenylamino)pyrene.

[0243] In the second EML 534, the host may be a carbazole derivative, and the dopant may be an iridium derivative (complex). For example, in the second EML 534, the host may be 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), and the dopant may be tris(2-phenylpyridine)iridium(III) (Ir(ppy)3).

[0244] The first CGL 570 includes a first n-type CGL 572 and a first p-type CGL 574. The first n-type CGL 572 is located between the first ETL 518 and the second HTL 532, and the first p-type CGL 574 is located between the first n-type CGL 572 and the second HTL 532.

[0245] The second CGL 580 includes a second n-type CGL 582 and a second p-type CGL 584. The second n-type CGL 582 is located between the second ETL 540 and the third HTL 552, and the second p-type CGL 584 is located between the second n-type CGL 582 and the third HTL 552.

[0246] The first n-type CGL 572 provides electrons to the first ETL 518, and the electrons are transported to the first EML 516 through the first ETL 518. The first p-type CGL 574 provides holes to the second HTL 532, and the holes are transported to the second EML 534 through the second HTL 532.

[0247] The second n-type CGL 582 provides electrons to the second ETL 540, and the electrons are transported to the second EML 534 through the second ETL 540. The second p-type CGL 584 provides holes to the third HTL 552, and the holes are transported to the third EML 554 through the third HTL 552.

[0248] Therefore, in the OLED D having a triple-stack (three-layer overlap) structure, the driving voltage is reduced and the emission efficiency is improved.

[0249] Each of the first n-type CGL 572 and the second n-type CGL 582 includes an n-type charge generation material and may have a thickness of 100 to 100 mm. For example, the n-type charge generation material may be Bphen. In addition, each of the first n-type CGL 572 and the second n-type CGL 582 may further include an auxiliary n-type charge generation material. For example, the auxiliary n-type charge generation material may be an alkali metal or an alkaline earth metal.

[0250] At least one of the HIL 520, the first p-type CGL 574, and the second p-type CGL 584 includes the organic compound of Formula 1-1 and at least one of the organic compound of Formula 2 and the organic compound of Formula 3. For example, the HIL 520 may include a first hole injection material 522 and a second hole injection material 524. In this case, the first hole injection material 522 is the organic compound of Formula 1-1, and the second hole injection material 524 includes at least one of a first compound 526, which is the organic compound of Formula 2, and a second compound 528, which is the organic compound of Formula 3. The first p-type CGL 574 may include a first p-type charge generation material 576 and a second p-type charge generation material 577. In this case, the first p-type charge generation material 576 is the organic compound of Formula 1-1, and the second p-type charge generation material 577 includes at least one of a third compound 578, which is the organic compound of Formula 2, and a fourth compound 579, which is the organic compound of Formula 3. The second p-type CGL 584 may include a third p-type charge generation material 586 and a fourth p-type charge generation material 587. In this case, the third p-type charge generation material 586 is the organic compound of Formula 1-1, and the fourth p-type charge generation material 587 includes at least one of a fifth compound 588 that is the organic compound of Formula 2 and a sixth compound 589 that is the organic compound of Formula 3.

[0251] The first hole injection material 522 in the HIL 520, the first p-type charge generation material 576 in the first p-type CGL 574, and the third p-type charge generation material 586 in the second p-type CGL 584 can be the same or different. Each of the first compound 526 and the second compound 528 in the HIL 520, and each of the third compound 578 and the fourth compound 579 in the first p-type CGL 574 can be the same or different. Each of the first compound 526 and the second compound 528 in the HIL 520, and each of the fifth compound 588 and the sixth compound 589 in the second p-type CGL 584 can be the same or different. Each of the third compound 578 and the fourth compound 579 in the first p-type CGL 574, and each of the fifth compound 588 and the sixth compound 589 in the second p-type CGL 584 can be the same or different.

[0252] In the HIL 520, the weight percentage of the first hole injection material 522 may be less than the weight percentage of the second hole injection material 524. That is, in the HIL 520, the second hole injection material 524 may be referred to as a host, and the first hole injection material 522 may be referred to as a dopant. For example, in the HIL 520, the first hole injection material 522 may have approximately 1 to 25 weight percent, and the second hole injection material 524 may have approximately 75 to 99 weight percent.

[0253] When the HIL 520 includes all of the first hole injection material 522, the first compound 526, and the second compound 528, the weight percentage of the first hole injection material 522 may be less than the weight percentage of each of the first and second compounds 526 and 528. In addition, the weight percentage of the first compound 526 may be equal to or greater than the weight percentage of the second compound 528. For example, the weight percentage ratio of the first compound 526 to the second compound 528 may be about 5:5 to 6:4. The HIL 520 may have a thickness of about 50 to 60 mm. thickness.

[0254] In the first p-type CGL 574, the weight percentage of the first p-type charge generation material 576 may be less than the weight percentage of the second p-type charge generation material 577. That is, in the first p-type CGL 574, the second p-type charge generation material 577 may be referred to as a host, and the first p-type charge generation material 576 may be referred to as a dopant. For example, in the first p-type CGL 574, the first p-type charge generation material 576 may have a weight percentage of approximately 1 to 25%, and the second p-type charge generation material 577 may have a weight percentage of approximately 75 to 99%.

[0255] When the first p-type CGL 574 includes all of the first p-type charge generation material 576, the third compound 578, and the fourth compound 579, the weight percentage of the first p-type charge generation material 576 may be less than the weight percentage of each of the third compound 578 and the fourth compound 579. In addition, the weight percentage of the third compound 578 may be equal to or greater than the weight percentage of the fourth compound 579. For example, the weight percentage ratio of the third compound 578 to the fourth compound 579 may be approximately 5:5 to 6:4. The first p-type CGL 574 may have a thickness of approximately 100 to 200 nm. thickness.

[0256] In the second p-type CGL 584, the weight percentage of the third p-type charge generation material 586 may be less than the weight percentage of the fourth p-type charge generation material 587. That is, in the second p-type CGL 584, the fourth p-type charge generation material 587 may be referred to as a host, and the third p-type charge generation material 586 may be referred to as a dopant. For example, in the second p-type CGL 584, the third p-type charge generation material 586 may have a weight percentage of approximately 1 to 25%, and the fourth p-type charge generation material 587 may have a weight percentage of approximately 75 to 99%.

[0257] When the second p-type CGL 584 includes all of the third p-type charge generation material 586, the fifth compound 588, and the sixth compound 589, the weight percentage of the third p-type charge generation material 586 may be less than the weight percentage of each of the fifth compound 588 and the sixth compound 589. In addition, the weight percentage of the fifth compound 588 may be equal to or greater than the weight percentage of the sixth compound 589. For example, the weight percentage ratio of the fifth compound 588 to the sixth compound 589 may be approximately 5:5 to 6:4. The second p-type CGL 584 may have a thickness of approximately 100 to 200 nm. thickness.

[0258] When the HIL 520 includes a first hole injection material 522, a first compound 526, and a second compound 528, the first p-type CGL 574 includes a first p-type charge generation material 576, a third compound 578, and a fourth compound 579, and the second p-type CGL 584 includes a third p-type charge generation material 586, a fifth compound 588, and a sixth compound 589, the weight percentage ratio of the first compound 726 to the second compound 528 in the HIL 520 may be less than each of the weight percentage ratio of the third compound 578 to the fourth compound 579 in the first p-type CGL 574 and the weight percentage ratio of the fifth compound 588 to the sixth compound 589 in the second p-type CGL 584. For example, the weight percentages of the first compound 526 and the second compound 528 in the HIL 520 may be the same, the weight percentage of the third compound 578 in the first p-type CGL 574 may be greater than the weight percentage of the fourth compound 579, and the weight percentage of the fifth compound 588 in the second p-type CGL 584 may be greater than the weight percentage of the sixth compound 589.

[0259] For example, when the HIL 520, the first p-type CGL 574, and the second p-type CGL 584 respectively include a first hole injection material 522 which is an organic compound in Formula 1-1, a first p-type charge generation material 576 which is an organic compound in Formula 1-1, and a third p-type charge generation material 586 which is an organic compound in Formula 1-1, the weight percentage of each of the first p-type charge generation material 576 and the third p-type charge generation material 586 in the first p-type CGL 574 and the second p-type CGL 584 may be equal to or greater than the weight percentage of the first hole injection material 522 in the HIL 520.

[0260] OLED D, which includes first and third emission sections 510 and 550 having wavelengths ranging from 440 to 480 nm, and second emission section 430 having a wavelength ranging from 500 to 550 nm, emits white light. Furthermore, a first CGL 570 including a first p-type charge generation material 576 and a second p-type charge generation material 577 is disposed between the first and second emission sections 510 and 530, and a second CGL 580 including a third p-type charge generation material 586 and a fourth p-type charge generation material 587 is disposed between the second and third emission sections 530 and 550. Consequently, OLED D offers advantages in terms of driving voltage, emission efficiency, and lifespan.

[0261] refer to Figure 4 , a second electrode 364 is formed on the first substrate 310 in which the organic emission layer 362 is formed.

[0262] In the organic light emitting display device 300 , since light emitted from the organic emission layer 362 is incident on the color filter layer 380 through the second electrode 364 , the second electrode 364 has a thin profile for transmitting the light.

[0263] The first electrode 360 ​​, the organic light emitting layer 362 , and the second electrode 364 constitute an OLED D.

[0264] The color filter layer 380 is positioned over the OLED D and includes a red filter 382, ​​a green filter 384, and a blue filter 386 corresponding to the red, green, and blue pixels RP, GP, and BP, respectively. The red filter 382 may include at least one of a red dye and a red pigment, the green filter 384 may include at least one of a green dye and a green pigment, and the blue filter 386 may include at least one of a blue dye and a blue pigment.

[0265] Although not shown, the color filter layer 380 may be attached to the OLED D by using an adhesive layer. Alternatively, the color filter layer 380 may be formed directly on the OLED D.

[0266] 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.

[0267] A polarizing plate (not shown) for reducing ambient light reflection may be disposed on the top-emission type OLED D. For example, the polarizing plate may be a circular polarizing plate.

[0268] exist Figure 4 In the OLED D, the first electrode 360 ​​and the second electrode 364 are a reflective electrode and a transparent (or semi-transparent) electrode, respectively, and the color filter layer 380 is provided on the OLED D. Alternatively, when the first electrode 360 ​​and the second electrode 364 are a transparent (or semi-transparent) electrode and a reflective electrode, respectively, the color filter layer 380 may be provided between the OLED D and the first substrate 310.

[0269] A color conversion layer (not shown) may be formed between the OLED D and the color filter layer 380. The color conversion layer may include a red conversion layer, a green conversion layer, and a blue conversion layer corresponding to the red, green, and blue pixels RP, GP, and BP, respectively. The red, green, and blue conversion layers convert white light from the OLED D into red, green, and blue light, respectively. For example, the color conversion layer may include quantum dots. Thus, the color purity of the organic light-emitting display device 300 can be further improved.

[0270] A color conversion layer may be included instead of the color filter layer 380 .

[0271] As described above, in the organic light emitting display device 300, the OLEDs D in the red, green, and blue pixels RP, GP, and BP emit white light, and the white light from the organic light emitting diodes D passes through the red color filter 382, ​​the green color filter 384, and the blue color filter 386. Therefore, red light, green light, and blue light are provided from the red pixel RP, the green pixel GP, and the blue pixel BP, respectively.

[0272] exist Figure 4 In the present invention, an OLED D emitting white light is used in a display device. Alternatively, the OLED D can be formed on the entire surface of a substrate, without requiring at least one of a driving element and a color filter layer for an illumination device. Display devices and illumination devices each including an OLED D of the present disclosure can be referred to as organic light-emitting devices.

[0273] In the OLED D and the organic light-emitting display device 300, at least one of the HIL and the p-type CGL includes the organic compound of Formula 1-1 and at least one of the organic compound of Formula 2 and the organic compound of Formula 3, thereby improving hole injection / transport performance toward the EML. Therefore, in the OLED D and the organic light-emitting display device 300, the driving voltage is reduced, and the emission efficiency and lifetime are improved.

[0274] [OLED1]

[0275] On the anode (ITO), HIL (HIL, NPD+HATCN (10 wt%)), the first HTL (HTL1, NPD), the first EML (EML1, Host (9,10-di(naphthalene-2-yl)anthracene) and dopant (1,6-bis(diphenylamino)pyrene, 3 wt%), first ETL (ETL1, 1,3,5-Tris(m-pyridin-3-ylphenyl)benzene (TmPyPB)), n-type CGL (N-CGL, Bphen+Li(2wt%)), p-type CGL (P-CGL, )、Second HTL (HTL2, NPD), the second EML (EML2, Host (CBP) and dopant (Ir(ppy)3, 8 wt%)), second ETL (ETL2, 2,2',2"-(1,3,5-phenyltriyl)-tris(1-phenyl-1-H-benzimidazole)(TPBi)), EIL(LiF, ) and cathode (Al, ) to form an OLED.

[0276] 1. Comparative Example

[0277] (1) Comparative Example 1 (Ref 1)

[0278] A p-type CGL was formed using NPD and HATCN (20 wt %).

[0279] (2) Comparative Example 2 (Ref2)

[0280] A p-type CGL was formed using compound H1-1 in Formula 5 and HATCN (20 wt %).

[0281] (3) Comparative Example 3 (Ref3)

[0282] A p-type CGL was formed using compound H2-8 in Formula 6 and HATCN (20 wt %).

[0283] (4) Comparative Example 4 (Ref4)

[0284] A p-type CGL was formed using compound H1-1 in Formula 5 (40 wt %), compound H2-8 in Formula 6 (40 wt %), and HATCN (20 wt %).

[0285] 2. Examples

[0286] (1) Example 1 (Ex1)

[0287] A p-type CGL was formed using compound H1-1 in Formula 5 and compound S07 in Formula 4 (20 wt %).

[0288] (2) Example 2 (Ex2)

[0289] A p-type CGL was formed using compound H2-8 in Formula 5 and compound S07 in Formula 4 (20 wt %).

[0290] (3) Example 3 (Ex3)

[0291] The p-type CGL was formed using compound H1-1 in Formula 5 (40 wt %), compound H2-8 in Formula 6 (40 wt %), and compound S07 in Formula 4 (20 wt %).

[0292] (4) Example 4 (Ex4)

[0293] A p-type CGL was formed using compound H1-1 in Formula 5 and compound S20 in Formula 4 (20 wt %).

[0294] (5) Example 5 (Ex5)

[0295] A p-type CGL was formed using compound H2-8 in Formula 5 and compound S20 in Formula 4 (20 wt %).

[0296] (6) Example 6 (Ex6)

[0297] The p-type CGL was formed using compound H1-1 in Formula 5 (40 wt %), compound H2-8 in Formula 6 (40 wt %), and compound S20 in Formula 4 (20 wt %).

[0298] (7) Example 7 (Ex7)

[0299] A p-type CGL was formed using Compound H1-1 in Formula 5 and Compound A13 in Formula 4 (20 wt %).

[0300] (8) Example 9 (Ex9)

[0301] A p-type CGL was formed using compound H2-8 in Formula 5 and compound A13 in Formula 4 (20 wt %).

[0302] (9) Example 9 (Ex9)

[0303] A p-type CGL was formed using compound H1-1 in Formula 5 (40 wt %), compound H2-8 in Formula 6 (40 wt %), and compound A13 in Formula 4 (20 wt %).

[0304] (10) Example 10 (Ex10)

[0305] A p-type CGL was formed using compound H1-15 in Formula 5 (40 wt %), compound H2-1 in Formula 6 (40 wt %), and compound A13 in Formula 4 (20 wt %).

[0306] In the OLEDs of Comparative Examples 1-4 (Ref1-Ref4) and Examples 1-10 (Ex1-Ex10), their characteristics, namely, driving voltage (V), efficiency (Cd / A), and lifespan (hr), were measured and listed in Table 1. The HOMO and LUMO energy levels of the organic compounds used in the p-type CGL were measured and listed in Table 2.

[0307] Table 1

[0308]

[0309] Table 2

[0310] HOMO(eV) LUMO(eV) HATCN -8.55 -6.07 S07 -8.21 -6.34 S20 -8.27 -6.46 A13 -8.22 -6.32 NPD -5.45 -2.18 H1-1 -5.46 -2.19 H1-15 -5.38 -2.12 H2-1 -5.51 -2.25 H2-8 -5.59 -2.28 H2-21 -5.56 -2.27

[0311] As shown in Table 1, compared to the OLED of Ref1 in which NPD and HATCN are used to form a p-type CGL, the OLEDs of Ref2 to Ref5 in which the organic compound of Formula 2 and / or the organic compound of Formula 3 are used together with HAT-CN to form a p-type CGL still have limitations in terms of driving voltage, emission efficiency, and lifespan. That is, even though the organic compound of Formula 2 and / or the organic compound of Formula 3 are used in the p-type CGL, the energy levels of the organic compound and HATCN (e.g., dopant) do not match, resulting in limitations in the performance of the OLEDs of Ref2 to Ref4.

[0312] On the other hand, in the OLEDs of Ex1 to Ex10, the p-type CGL includes a compound of formula 1-1 (i.e., compound S07, compound S20 or compound A13), and at least one of the compound of formula 2 (i.e., compound H1-1 or compound H1-15) and the compound of formula 3 (i.e., compound H2-1 or compound H2-8), and the driving voltage is significantly reduced, and the emission efficiency and lifespan are significantly increased.

[0313] Furthermore, in the OLEDs of Ex3, Ex6, Ex9, and Ex10, in which the compounds of Formula 2 and Formula 3, as well as the compound of Formula 1-1, are included in the p-type CGL, the driving voltage is further reduced, and the emission efficiency and lifetime are further increased. Furthermore, in the OLEDs of Ex7 to Ex10, in which the p-type CGL includes an indacene derivative having an asymmetric structure, the driving voltage is significantly reduced, and the emission efficiency and lifetime are significantly increased.

[0314] [OLED2]

[0315] HIL (HIL, )、HTL(HTL, NPD)、EML(EML, Host (9,10-di(naphthalene-2-yl)anthracene) and dopant (1,6-bis(diphenylamino)pyrene, 3 wt%)), ETL (ETL, TmPyPB)、EIL(LiF, ) and cathode (Al, ) to form an OLED.

[0316] 3. Comparative Example

[0317] (1) Comparative Example 5 (Ref5)

[0318] The HIL was formed using NPD and HATCN (20 wt %).

[0319] (2) Comparative Example 6 (Ref6)

[0320] The HIL was formed using compound H1-1 of Formula 5 and HATCN (20 wt %).

[0321] (3) Comparative Example 7 (Ref7)

[0322] The HIL was formed using compound H2-8 of Formula 6 and HATCN (20 wt %).

[0323] (3) Comparative Example 8 (Ref8)

[0324] The HIL was formed using compound H1-1 of Formula 5 (40 wt %), compound H2-8 of Formula 6 (40 wt %), and HATCN (20 wt %).

[0325] 4. Examples

[0326] (1) Example 11 (Ex11)

[0327] The HIL was formed using compound H1-1 of Formula 5 and compound A13 of Formula 4 (20 wt %).

[0328] (2) Example 12 (Ex12)

[0329] The HIL was formed using compound H2-8 of Formula 5 and compound A13 of Formula 4 (20 wt %).

[0330] (3) Example 13 (Ex13)

[0331] The HIL was formed using compound H1-1 in Formula 5 (40 wt %), compound H2-8 in Formula 5 (40 wt %), and compound A13 in Formula 4 (20 wt %).

[0332] (4) Example 14 (Ex14)

[0333] The HIL was formed using compound H1-15 in Formula 5 (40 wt %), compound H2-1 in Formula 5 (40 wt %), and compound A13 in Formula 4 (20 wt %).

[0334] In the OLEDs of Comparative Examples 5-8 (Ref5-Ref8) and Examples 11-14 (Ex11-Ex14), their characteristics, ie, driving voltage (V), efficiency (Cd / A), and lifespan (hr), were measured and listed in Table 3.

[0335] Table 3

[0336]

[0337] As shown in Table 3, compared with the OLEDs of Ref4 to Ref8, in the OLEDs of Ex11 to Ex14, in which the compound of Formula 1-1 (i.e., compound A13) and at least one of the compound of Formula 2 (i.e., compound H1-1 or compound H1-15) and the compound of Formula 3 (i.e., compound H2-1 or compound H2-8) are included in the p-type CGL, the driving voltage is significantly reduced, and the emission efficiency and lifetime are significantly increased.

[0338] Furthermore, in the OLEDs of Ex13 and Ex14, in which the compounds of Formula 2 and Formula 3 as well as the compound of Formula 1-1 are included in the p-type CGL, the driving voltage is further reduced, and the emission efficiency and lifetime are further increased.

[0339] It will be apparent to those skilled in the art that various modifications and variations may be made to the embodiments of the present disclosure without departing from the spirit or scope of the present disclosure. Therefore, as long as these modifications and variations fall within the scope of the appended claims and their equivalents, these modifications and variations are included in the present disclosure.

Claims

1. An organic light emitting diode, comprising: a first electrode; a second electrode facing the first electrode; and a first emission portion, the first emission portion including a first emission material layer and a hole injection layer, and located between the first electrode and the second electrode, The hole injection layer includes a first hole injection material and a second hole injection material, and is located between the first electrode and the first emission material layer. The first hole injection material is an organic compound of formula 1-1: [Formula 1-1] wherein R1 and R2 are each independently selected from hydrogen (H), deuterium (D), halogen and cyano, wherein each of R3 to R6 is independently selected from halogen, cyano, malononitrile, C1-C10 haloalkyl and C1-C10 haloalkoxy, and at least one of R3 and R4 and at least one of R5 and R6 is malononitrile, wherein X and Y are each independently a phenyl group substituted with at least one of a C1-C10 alkyl group, a halogen group, a cyano group, a malononitrile group, a C1-C10 haloalkyl group, and a C1-C10 haloalkoxy group, The second hole injection material includes both the first compound in Formula 2 and the second compound in Formula 3: [Formula 2] and [Formula 3] Wherein in Formula 2, X1 and X2 are each independently selected from C6-C30 aryl and C5-C30 heteroaryl, and L1 is selected from C6-C30 arylene and C5-C30 heteroarylene, Where a is 0 or 1, wherein each of R1 to R14 is independently selected from H, D, C1-C10 alkyl, C6-C30 aryl and C5-C30 heteroaryl, or adjacent two of R1 to R14 are connected to each other to form a condensed ring, Wherein in Formula 3, Y1 and Y2 are each independently selected from C6-C30 aryl and C5-C30 heteroaryl, L1 is selected from C6-C30 arylene and C5-C30 heteroarylene, Where b is 0 or 1, wherein each of R21 to R34 is independently selected from H, D, C1-C10 alkyl, C6-C30 aryl, and C5-C30 heteroaryl, or adjacent two of R21 to R34 are connected to each other to form a fused ring; The weight percentage of the first hole injection material is less than the weight percentage of each of the first compound and the second compound.

2. The organic light emitting diode according to claim 1, wherein the hole injection layer comprises the first hole injection material, the first compound and the second compound, and The weight percentage of the first compound is equal to or greater than the weight percentage of the second compound.

3. An organic light emitting diode, comprising: a first electrode; a second electrode facing the first electrode; and a first emission portion, the first emission portion including a first emission material layer and a hole injection layer, and located between the first electrode and the second electrode, The hole injection layer includes a first hole injection material and a second hole injection material, and is located between the first electrode and the first emission material layer. The first hole injection material is an organic compound of formula 1-1: [Formula 1-1] wherein R1 and R2 are each independently selected from hydrogen (H), deuterium (D), halogen and cyano, wherein each of R3 to R6 is independently selected from halogen, cyano, malononitrile, C1-C10 haloalkyl and C1-C10 haloalkoxy, and at least one of R3 and R4 and at least one of R5 and R6 is malononitrile, wherein X and Y are each independently a phenyl group substituted with at least one of a C1-C10 alkyl group, a halogen group, a cyano group, a malononitrile group, a C1-C10 haloalkyl group, and a C1-C10 haloalkoxy group, The second hole injection material includes both the first compound in Formula 2 and the second compound in Formula 3: [Formula 2] and [Formula 3] Wherein in Formula 2, X1 and X2 are each independently selected from C6-C30 aryl and C5-C30 heteroaryl, and L1 is selected from C6-C30 arylene and C5-C30 heteroarylene, Where a is 0 or 1, wherein each of R1 to R14 is independently selected from H, D, C1-C10 alkyl, C6-C30 aryl and C5-C30 heteroaryl, or adjacent two of R1 to R14 are connected to each other to form a condensed ring, Wherein in Formula 3, Y1 and Y2 are each independently selected from C6-C30 aryl and C5-C30 heteroaryl, L1 is selected from C6-C30 arylene and C5-C30 heteroarylene, where b is 0 or 1, and wherein each of R21 to R34 is independently selected from H, D, C1-C10 alkyl, C6-C30 aryl, and C5-C30 heteroaryl, or adjacent two of R21 to R34 are connected to each other to form a fused ring; The weight percentage of the first compound is equal to or greater than the weight percentage of the second compound.

4. The organic light emitting diode according to any one of claims 1 to 3, wherein the first hole injection material is represented by one of Formulas 1-2 to 1-4: [Formula 1-2] [Formula 1-3] and [Formula 1-4] Wherein in Formula 1-4, each of X1 to X3 and each of Y1 to Y3 are independently selected from H, C1-C10 alkyl, halogen, cyano, malononitrile, C1-C10 haloalkyl and C1-C10 haloalkoxy, and satisfy at least one of the following conditions: i) X1 and Y1 are different, and ii) X2 is different from Y2 and Y3, or X3 is different from Y2 and Y3.

5. The organic light emitting diode according to any one of claims 1 to 3, wherein the first hole injection material is one of the compounds of Formula 4: [Formula 4] 6. The organic light emitting diode according to any one of claims 1 to 3, wherein the first compound is one of the compounds of Formula 5: [Formula 5] 7. The organic light emitting diode according to any one of claims 1 to 3, wherein the second compound is one of the compounds of Formula 6: [Formula 6] 8. The organic light emitting diode according to claim 1 or 3, further comprising: a second emitting portion, the second emitting portion comprising a second emitting material layer and located between the first emitting portion and the second electrode; and A first p-type charge generation layer includes a first p-type charge generation material and a second p-type charge generation material and is located between the first emission portion and the second emission portion. 9 . The organic light emitting diode according to claim 8 , wherein the first p-type charge generation material is the organic compound of Formula 1-1, and the second p-type charge generation material comprises at least one of the third compound of Formula 2 and the fourth compound of Formula 3.

10. The organic light emitting diode according to claim 9, wherein: In the first p-type charge generation layer, a weight percentage of the first p-type charge generation material is less than a weight percentage of the second p-type charge generation material.

11. The organic light emitting diode according to claim 9, wherein: The first p-type charge generation layer includes the first p-type charge generation material, the third compound, and the fourth compound, and The weight percentage of the first p-type charge generating material is less than the weight percentage of each of the third compound and the fourth compound.

12. The organic light emitting diode according to claim 9, wherein: The first p-type charge generation layer includes the first p-type charge generation material, the third compound, and the fourth compound, and The weight percentage of the third compound is equal to or greater than the weight percentage of the fourth compound.

13. The organic light emitting diode according to claim 9, wherein the hole injection layer comprises the first hole injection material, the first compound, and the second compound, and the first p-type charge generation layer comprises the first p-type charge generation material, the third compound, and the fourth compound, and The weight percentage ratio of the first compound to the second compound is smaller than the weight percentage ratio of the third compound to the fourth compound. 14 . The organic light emitting diode according to claim 13 , wherein the first compound and the second compound have the same weight percentage, and the weight percentage of the third compound is greater than the weight percentage of the fourth compound.

15. The organic light emitting diode according to claim 8, wherein: The first emitting material layer has an emission wavelength range of 440 to 480 nm, and the second emitting material layer has an emission wavelength range of 500 to 550 nm.

16. The organic light emitting diode according to claim 8, further comprising: a third emitting portion, the third emitting portion comprising a third emitting material layer and located between the second emitting portion and the second electrode; and A second p-type charge generation layer includes a third p-type charge generation material and a fourth p-type charge generation material and is located between the second emission portion and the third emission portion. 17 . The organic light emitting diode according to claim 16 , wherein the third p-type charge generation material is the organic compound of Formula 1-1, and the fourth p-type charge generation material comprises at least one of the fifth compound of Formula 2 and the sixth compound of Formula 3.

18. The organic light emitting diode according to claim 17, wherein: In the second p-type charge generation layer, a weight percentage of the third p-type charge generation material is less than a weight percentage of the fourth p-type charge generation material.

19. The organic light emitting diode according to claim 17, wherein: The second p-type charge generation layer includes the third p-type charge generation material, the fifth compound, and the sixth compound, and wherein a weight percentage of the third p-type charge generation material is less than a weight percentage of each of the fifth compound and the sixth compound.

20. The organic light emitting diode according to claim 17, wherein: The second p-type charge generation layer includes the third p-type charge generation material, the fifth compound, and the sixth compound, and The weight percentage of the fifth compound is equal to or greater than the weight percentage of the sixth compound.

21. The organic light emitting diode according to claim 16, wherein: Each of the first emitting material layer and the third emitting material layer has an emission wavelength range of 440 to 480 nm, and the second emitting material layer has an emission wavelength range of 500 to 550 nm.

22. An organic light emitting diode, comprising: a first electrode; a second electrode facing the first electrode; a first emitting portion, the first emitting portion comprising a first emitting material layer and located between the first electrode and the second electrode; a second emitting portion, the second emitting portion comprising a second emitting material layer and located between the first emitting portion and the second electrode; and a first p-type charge generation layer, the first p-type charge generation layer including a first p-type charge generation material and a second p-type charge generation material, and being located between the first emission portion and the second emission portion; The first p-type charge generating material is an organic compound in Formula 1-1: [Formula 1-1] wherein R1 and R2 are each independently selected from hydrogen (H), deuterium (D), halogen and cyano, wherein each of R3 to R6 is independently selected from halogen, cyano, malononitrile, C1-C10 haloalkyl and C1-C10 haloalkoxy, and at least one of R3 and R4 and at least one of R5 and R6 is malononitrile, wherein X and Y are each independently a phenyl group substituted with at least one of a C1-C10 alkyl group, a halogen group, a cyano group, a malononitrile group, a C1-C10 haloalkyl group, and a C1-C10 haloalkoxy group, The second p-type charge generating material includes both the first compound in Formula 2 and the second compound in Formula 3: [Formula 2] and [Formula 3] Wherein in Formula 2, X1 and X2 are each independently selected from C6-C30 aryl and C5-C30 heteroaryl, and L1 is selected from C6-C30 arylene and C5-C30 heteroarylene, Where a is 0 or 1, wherein each of R1 to R14 is independently selected from H, D, C1-C10 alkyl, C6-C30 aryl and C5-C30 heteroaryl, or adjacent two of R1 to R14 are connected to each other to form a condensed ring, Wherein in Formula 3, Y1 and Y2 are each independently selected from C6-C30 aryl and C5-C30 heteroaryl, L1 is selected from C6-C30 arylene and C5-C30 heteroarylene, Where b is 0 or 1, wherein each of R21 to R34 is independently selected from H, D, C1-C10 alkyl, C6-C30 aryl, and C5-C30 heteroaryl, or adjacent two of R21 to R34 are connected to each other to form a fused ring; The weight percentage of the first p-type charge generating material is less than the weight percentage of each of the first compound and the second compound.

23. The organic light emitting diode according to claim 22, wherein the first p-type charge generating material is represented by one of Formulas 1-2 to 1-4: [Formula 1-2] [Formula 1-3] and [Formula 1-4] Wherein in Formula 1-4, each of X1 to X3 and each of Y1 to Y3 are independently selected from H, C1-C10 alkyl, halogen, cyano, malononitrile, C1-C10 haloalkyl and C1-C10 haloalkoxy, and satisfy at least one of the following conditions: i) X1 and Y1 are different, and ii) X2 is different from Y2 and Y3, or X3 is different from Y2 and Y3.

24. The organic light emitting diode according to claim 22, wherein the first p-type charge generating material is one of the compounds of Formula 4: [Formula 4] 25. The organic light emitting diode according to claim 22, wherein the first compound is one of the compounds of Formula 5: [Formula 5] 26. The organic light emitting diode according to claim 22, wherein the second compound is one of the compounds of Formula 6: [Formula 6] 27. The organic light emitting diode according to claim 22, further comprising: a third emitting portion, the third emitting portion comprising a third emitting material layer and located between the second emitting portion and the second electrode; and A second p-type charge generation layer includes a third p-type charge generation material and a fourth p-type charge generation material and is located between the second emission portion and the third emission portion. 28 . The organic light emitting diode according to claim 27 , wherein the third p-type charge generation material is the organic compound of Formula 1-1, and the fourth p-type charge generation material comprises at least one of the fifth compound of Formula 2 and the sixth compound of Formula 3.

29. The organic light emitting diode according to claim 28, wherein: In the second p-type charge generation layer, a weight percentage of the third p-type charge generation material is less than a weight percentage of the fourth p-type charge generation material.

30. An organic light-emitting device, comprising: substrate; The organic light emitting diode according to claim 1, which is located on the substrate; and An encapsulation film covers the organic light emitting diode.

31. The organic light-emitting device according to claim 30, wherein: A red pixel, a green pixel, and a blue pixel are defined on the substrate, and the organic light emitting device corresponds to each of the red pixel, the green pixel, and the blue pixel, and The organic light-emitting device further comprises: A color filter layer is provided 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.

32. An organic light-emitting device, comprising: substrate; The organic light emitting diode according to claim 22, which is located on the substrate; and An encapsulation film covers the organic light emitting diode.

33. The organic light-emitting device according to claim 32, 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 The organic light-emitting device further comprises: A color filter layer is provided 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.

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