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, wherein the first emission portion is located between the first and second electrodes and comprises a first emission material layer, a hole injection layer located between the first electrode and the first emission material layer, and a first hole transport layer located between the hole injection layer and the first emission material layer, wherein the hole injection layer comprises a hole injection material, and the first hole transport layer comprises at least one of a first hole transport material and a second hole transport material, and wherein the first hole transport material and the second hole transport material are fluorene derivatives having different structures.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of Korean Patent Application No. 10-2020-0179672, 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 being located between the first electrode and the second electrode and comprising a first emission material layer, a hole injection layer located between the first electrode and the first emission material layer, and a first hole transport layer located between the hole injection layer and the first emission material layer, wherein the hole injection layer comprises a hole injection material, and the hole injection material is an organic compound represented by Formula 1-1: [Formula 1-1]

[0013] 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 first hole transport layer comprises at least one of a first hole transport material represented by Formula 2 and a second hole transport material represented by Formula 3:

[0014] [Formula 2]

[0015] and

[0016] [Formula 3]

[0017] 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.

[0018] 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.

[0019] 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

[0020] 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.

[0021] Figure 1 is a schematic circuit diagram of an organic light emitting display device disclosed herein.

[0022] Figure 2 is a schematic cross-sectional view of an organic light-emitting device according to a first embodiment of the present disclosure.

[0023] Figure 3 is a schematic cross-sectional view of an OLED according to a second embodiment of the present disclosure.

[0024] Figure 4 is a schematic cross-sectional view of an organic light-emitting device according to a third embodiment of the present disclosure.

[0025] Figure 5 is a schematic cross-sectional view of an OLED according to a fourth embodiment of the present disclosure.

[0026] Figure 6 is a schematic cross-sectional view of an OLED according to a fifth embodiment of the present disclosure. DETAILED DESCRIPTION

[0027] Reference will now be made in detail to some examples and preferred embodiments illustrated in the accompanying drawings.

[0028] 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.

[0029] Figure 1 is a schematic circuit diagram of an organic light emitting display device disclosed herein.

[0030] 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.

[0031] 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.

[0032] 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. This allows the organic light-emitting display device to display the desired image.

[0033] Figure 2 is a schematic cross-sectional view of an organic light emitting display device according to a first embodiment of the present disclosure.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] A semiconductor layer 122 is formed on the buffer layer 120. The semiconductor layer 122 may include an oxide semiconductor material or polysilicon.

[0038] 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.

[0039] 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.

[0040] 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 .

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] A source electrode 140 and a drain electrode 142 formed of a conductive material (eg, metal) are formed on the interlayer insulating layer 132 .

[0046] 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.

[0047] 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 ).

[0048] 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.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] 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.

[0053] 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).

[0054] 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.

[0055] 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.

[0056] 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, a hole injection layer (HIL) below the EML, and a hole transport layer (HTL) between the EML and the HIL. Furthermore, the organic emission layer 162 may further include at least one of an electron blocking layer (EBL), a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL).

[0057] As described below, the HIL includes an indacene derivative substituted with a malononitrile group (e.g., an indacene compound) as a hole injection material, and the HTL includes fluorene derivatives with different structures as first and second hole transport materials. Thus, holes are efficiently injected and transported from the anode to the EML.

[0058] 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).

[0059] 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.

[0060] The first electrode 160 , the organic emission layer 162 , and the second electrode 164 constitute an OLED D.

[0061] 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.

[0062] 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.

[0063] 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.

[0064] 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.

[0065] Figure 3 is a schematic cross-sectional view of an OLED according to a second embodiment.

[0066] like Figure 3As 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, a HIL 210 located between the first electrode 160 and the EML 240, and a HTL 220 located between the HIL 210 and the EML 240.

[0067] 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.

[0068] Holes are injected and transported from the first electrode 160 to the EML 240 through the HIL 210 and the HTL 220 , and electrons are transported from the second electrode 164 to the EML.

[0069] The organic emission layer 162 may further include at least one of an EIL 260 positioned between the second electrode 164 and the EML 240 , and an ETL 250 positioned between the EML 240 and the EIL 260 .

[0070] 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 .

[0071] For example, 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 200-300 nm. Preferred

[0072] 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

[0073] 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-hydroxyquinoline)aluminum (Alq3), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 3-(4-biphenyl)-4-phenyl-5-tert-butyl Phenyl-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-(phenylphenol)aluminum (BAlq), but are not limited thereto. For example, ETL 250 may include an azine-based compound such as TmPyPB, or an imidazole-based compound such as TPBi, and may have a carbonyl group of 50 to 100 carbon atoms. Thickness, preferably

[0074] 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

[0075] 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.

[0076] 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.

[0077] 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.

[0078] 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.

[0079] The HIL 210 includes a hole injection material 212 that is an indacene derivative (eg, an indacene-based organic compound) substituted with malononitrile. The hole injection material 212 is represented by Formula 1-1.

[0080] [Formula 1-1]

[0081]

[0082] 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.

[0083] 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.

[0084] 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.

[0085] 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.

[0086] [Formula 1-2]

[0087]

[0088] [Formula 1-3]

[0089]

[0090] 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.

[0091] 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.

[0092] For example, the first hole injection material 212 in Formula 1-1 may be represented by Formula 1-4.

[0093] [Formula 1-4]

[0094]

[0095] 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.

[0096] The hole injection material 212 has excellent hole injection performance, so that the hole injection performance from the first electrode 160 as an anode is improved.

[0097] The HTL 220 contacts the HIL 210 and is disposed under the EML 240. The HTL 220 may have a thickness of about 500 to 1000 mm. Thickness, preferably But it is not limited to this.

[0098] The HTL 220 includes at least one of a first hole transport material 222 and a second hole transport material 224. That is, the HTL 220 may be formed of only the first hole transport material 222, only the second hole transport material, or a mixture of the first hole transport material 222 and the second hole transport material 224. The first hole transport material 222 and the second hole transport material 224 are fluorene derivatives (or spirofluorene derivatives) having different structures and properties.

[0099] The first hole transport material 222 may be represented by Formula 2.

[0100] [Formula 2]

[0101]

[0102] 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.

[0103] 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.

[0104] 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.

[0105] 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).

[0106] 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.

[0107] The second hole transport material 224 may be represented by Formula 3.

[0108] [Formula 3]

[0109]

[0110] 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.

[0111] 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.

[0112] The first hole transport material 222 and the second hole transport material 224 differ in the attachment position of the amine moiety (or amino group) or the linker L1. That is, in the first hole transport material 222, the amine moiety is attached to the second position of the fluorene moiety (or spirofluorene moiety), while in the second hole transport material 224, the amino moiety is attached to the third position of the fluorene moiety (or spirofluorene moiety).

[0113] The highest occupied molecular orbital (HOMO) energy level of the first hole transport material 222 is lower than the highest occupied molecular orbital energy level of the second hole transport material 224. For example, the first hole transport material 222 may have a HOMO energy level higher than -5.50 eV, and the second hole transport material 224 may have a HOMO energy level equal to or lower than -5.50 eV.

[0114] When an EBL including an electron blocking material is formed between the HTL 220 and the EML 240, the HOMO energy level of the second hole transport material 224 is higher than the HOMO energy level of the electron blocking material. The difference between the HOMO energy levels of the second hole transport material 224 and the electron blocking material may be 0.3 eV or less. For example, the electron blocking material may be TCTA.

[0115] The first hole transport material 222 lowers the energy barrier between the HIL 210 and the HTL 220, and the second hole transport material 224 lowers the energy barrier between the HTL 220 and the EML 240. Therefore, hole transport efficiency from the HIL 210 is improved.

[0116] When the first hole transport material 222 and the second hole transport material 224 are included in the HTL 220, the first hole transport material 222 and the second hole transport material 224 may have the same or different weight percentages. For example, the weight percentage of the first hole transport material 222 may be equal to or greater than the weight percentage of the second hole transport material 224.

[0117] The hole injection material in Formula 1-1 may be one of the compounds in Formula 4.

[0118] [Formula 4]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125] The first hole transport material 222 in Formula 2 may be one of the compounds in Formula 5.

[0126] [Formula 5]

[0127]

[0128]

[0129] The second hole transport material 224 in Formula 3 may be one of the compounds in Formula 6.

[0130] [Formula 6]

[0131]

[0132]

[0133] [synthesis]

[0134] 1. Synthesis of Compound A04

[0135] (1) Compound 4-A

[0136] [Reaction formula 1-1]

[0137]

[0138] 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)

[0139] (2) Compound 4-B

[0140] [Reaction formula 1-2]

[0141]

[0142] 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).

[0143] (3) Compound 4-C

[0144] [Reaction formula 1-3]

[0145]

[0146] 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)

[0147] (4) Compound A04

[0148] [Reaction formula 1-4]

[0149]

[0150] 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)

[0151] 2. Synthesis of Compound A13

[0152] (1) Compound 13-A

[0153] [Reaction formula 2-1]

[0154]

[0155] 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)

[0156] (2) Compound 13-B

[0157] [Reaction formula 2-2]

[0158]

[0159] 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)

[0160] (3) Compound 13-C

[0161] [Reaction formula 2-3]

[0162]

[0163] 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)

[0164] (4) Compound A13

[0165] [Reaction formula 2-4]

[0166]

[0167] 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)

[0168] 3. Synthesis of Compound A37

[0169] (1) Compound 37-A

[0170] [Reaction formula 3-1]

[0171]

[0172] 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)

[0173] (2) Compound 37-B

[0174] [Reaction formula 3-2]

[0175]

[0176] 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)

[0177] (3) Compound 37-C

[0178] [Reaction formula 3-3]

[0179]

[0180] 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)

[0181] (4) Compound 37

[0182] [Reaction formula 3-4]

[0183]

[0184] 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)

[0185] The HIL 210 may further include a hole injection host material (not shown). That is, the HIL 210 may be formed of only the hole injection material 212 that is the organic compound in Formula 1-1, or may be formed of a mixture of the hole injection material 212 and a hole injection host material.

[0186] The hole injection host material may include at least one of the following: 4,4',4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (NATA), 4,4',4"-tris(N-(naphthalene-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazolyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4"- The hole injection host material may be, but is not limited to, NPD, 1,4,5,8,9,11-hexaazatriphenylene hexacarbonitrile (dipyrazino[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene)polystyrenesulfonate (PEDOT / PSS), and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine. For example, the hole injection host material may be NPD. In this case, the hole injection material 212 may have a concentration of about 1-40 wt%, preferably about 5-20 wt%, in the HIL 210.

[0187] As described above, in the OLED of the present disclosure, the HIL 210 includes the hole injection material 212, which is the organic compound in Formula 1-1, and the HTL 220 includes at least one of the first hole transport material 222, which is the organic compound in Formula 2, and the second hole transport material 224, which is the organic compound in Formula 3. Therefore, the hole injection and transport efficiency from the first electrode 160 to the EML 240 is improved. Therefore, in the OLED D of the present disclosure, the driving voltage is reduced, and the emission efficiency and lifespan are improved.

[0188] 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.

[0189] 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.

[0190] 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.

[0191] 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.

[0192] A semiconductor layer 322 is formed on the buffer layer 320. The semiconductor layer 322 may include an oxide semiconductor material or polysilicon.

[0193] 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.

[0194] 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 .

[0195] 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.

[0196] 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.

[0197] A source electrode 340 and a drain electrode 342 formed of a conductive material (eg, metal) are formed on the interlayer insulating layer 332 .

[0198] 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.

[0199] 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 ).

[0200] 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.

[0201] 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.

[0202] 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.

[0203] 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.

[0204] 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.

[0205] An organic emission layer 362 is formed on the first electrode 360 .

[0206] 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, the first emission portion 410 includes a HIL 420, a first HTL 424 and a first EML 416, and the second emission portion 430 includes a second HTL 440 and a second EML 432.

[0207] 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.

[0208] In the first emission portion 410, the HIL 420 is located under the first EML 416, and the first HTL 424 is located between the HIL 420 and the first EML 416. That is, the HIL 420 is located between the first electrode 360 and the first EML 416.

[0209] The first transmitting portion 410 may further include a first ETL 418 over the first EML 416 .

[0210] Although not shown, the first transmitting portion 410 may further include at least one of an EBL between the first HTL 424 and the first EML 416 and an HBL between the first EML 416 and the first ETL 418. For example, the EBL may include a TCTA.

[0211] In the second emission portion 430 , the second HTL 440 is located under the second EML 432 .

[0212] The second transmitting portion 430 may further include at least one of an EIL 436 over the second EML 432 and a second ETL 434 between the second EML 432 and the EIL 436 .

[0213] Although not shown, the second transmitting portion 430 may further include at least one of an EBL located between the second HTL 440 and the second EML 432 and an HBL located between the second EML 432 and the second ETL 434. For example, the EBL may include a TCTA.

[0214] One of the first EML 416 and the second EML 432 provides light having a wavelength range of approximately 440 to 480 nm, and the other of the first EML 416 and the second EML 432 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 432 may provide light having a wavelength range of approximately 500 to 550 nm. Alternatively, the second EML 432 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.

[0215] 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 432 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).

[0216] 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 440, and the p-type CGL 454 is located between the n-type CGL 452 and the second HTL 440.

[0217] 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 440, and the holes are transferred to the second EML 432 through the second HTL 440. Therefore, in the OLED D having a two-stack (double-stack) structure, the driving voltage is reduced and the emission efficiency is improved.

[0218] 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).

[0219] 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.

[0220] At least one of the HIL 420 and the p-type CGL 454 includes the organic compound of Formula 1-1. For example, the HIL 420 may include the organic compound of Formula 1-1 as the hole injection material 422, and the p-type CGL 454 may include the organic compound of Formula 1-1 as the p-type charge generation material 456.

[0221] The hole injection material 422 in the HIL 420 and the p-type charge generation material 456 in the p-type CGL 454 may be the same or different.

[0222] The HIL 420 may have a When the HIL 420 includes the organic compound of Formula 1-1 as the hole injection material 422, the HIL 420 may further include a hole injection host material (not shown). That is, the HIL 420 may be formed of only the hole injection material 422 that is the organic compound of Formula 1-1, or may be formed of a mixture of the hole injection material 422 and a hole injection host material.

[0223] The hole injection host material may be NPD. In this case, the hole injection material 422 may have about 1-40 wt%, preferably about 5-20 wt%, in the HIL 420.

[0224] The p-type CGL 454 may have a When the p-type CGL 454 includes the organic compound of Formula 1-1 as the p-type charge-generating material 456, the p-type CGL 454 may further include a p-type charge-generating host material (not shown). That is, the p-type CGL 454 may be formed only of the p-type charge-generating material 456, which is the organic compound of Formula 1-1, or may be formed of a mixture of the p-type charge-generating material 456 and the p-type charge-generating host material.

[0225] For example, the p-type charge generation host material may include at least one of the following: 4,4',4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (NATA), 4,4',4"-tris(N-(naphthalene-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazolyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4"- The p-type charge generation host material may be, but is not limited to, NPD, 1,4,5,8,9,11-hexaazatriphenylene hexacarbonitrile (dipyrazino[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene)polystyrenesulfonate (PEDOT / PSS), and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine. For example, the p-type charge generation host material may be NPD. In this case, the p-type charge generation material 456 may have a weight percentage of about 1-40%, preferably about 10-30%, in the p-type CGL 454.

[0226] When the HIL 420 includes the hole injection host material and the hole injection material 422 in Formula 1-1, and the p-type CGL 454 includes the p-type charge generation host material and the p-type charge generation material 456, the weight percentage of the p-type charge generation material 456 in the p-type CGL 454 can be equal to or greater than the weight percentage of the hole injection material 422 in the HIL 420.

[0227] At least one of the first HTL 424 and the second HTL 440 includes at least one of a first hole transport material that is an organic compound in Formula 2 and a second hole transport material that is an organic compound in Formula 3. For example, the first HTL 424 may include at least one of a first hole transport material 426 that is an organic compound in Formula 2 and a second hole transport material 428 that is an organic compound in Formula 3, and the second HTL 440 may include at least one of a first hole transport material 442 that is an organic compound in Formula 2 and a second hole transport material 444 that is an organic compound in Formula 3.

[0228] That is, the first HTL 424 may be formed of only the first hole transport material 426, may be formed of only the second hole transport material 428, or may be formed of a mixture of the first hole transport material 426 and the second hole transport material 428. The second HTL 440 may be formed of only the first hole transport material 442, may be formed of only the second hole transport material 444, or may be formed of a mixture of the first hole transport material 442 and the second hole transport material 444.

[0229] When the first hole transport material 426 and the second hole transport material 428 are included in the first HTL 424 and the first hole transport material 442 and the second hole transport material 444 are included in the second HTL 440, the first hole transport material 426 has a first weight percentage in the first HTL 424, and the first hole transport material 442 has a second weight percentage less than the first weight percentage in the second HTL 440. In other words, the weight percentage of the second hole transport material 444 in the second HTL 440 may be greater than the weight percentage of the second hole transport material 428 in the first HTL 424. Since the second HTL 440 is closer to the second electrode 364, which is a cathode, than the first HTL 424, the weight percentage of the second hole transport material 444 in the second HTL 440 increases, so that the emission region in the second EML 432 can be prevented from moving toward the second HTL 440. Therefore, the emission region in the second EML 432 may be present at the center of the second EML 432, and the emission efficiency and lifespan of the OLED D may be improved.

[0230] The thickness of the first HTL 424 may be greater than that of the second HTL 440. For example, the first HTL 424 may have a thickness of about 500 to 1000 mm. Thickness, preferably And the second HTL 440 may have a thickness of about 200 to Thickness, preferably

[0231] The OLED D includes a first emission part 410 having a wavelength range of 440 to 480 nm and a second emission part 430 having a wavelength range of 500 to 550 nm, and provides white light emission, with the CGL 450 disposed between the first emission part 410 and the second emission part 430. Therefore, the OLED D has advantages in driving voltage, emission efficiency, and lifespan.

[0232] In addition, at least one of the HIL 420 and the p-type CGL 454 includes the organic compound of Formula 1-1, and at least one of the first HTL 424 and the second HTL 440 includes at least one of the organic compound of Formula 2 and the organic compound of Formula 3. Therefore, in the OLED D, the driving voltage is further reduced, and the emission efficiency and lifespan are further improved.

[0233] refer to Figure 6 , the organic emission layer 362 includes: a first emission portion 510, which includes a HIL 520, a first HTL 524 and a first EML 516; a second emission portion 530, which includes a second HTL 540 and a second EML 534; a third emission portion 550, which includes a third HTL 560 and a third EML 552; 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.

[0234] 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 stacked in sequence 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 CGL 580 and the second electrode 364.

[0235] In the first emission portion 510, the HIL 520 is located under the first EML 516, and the first HTL 524 is located between the HIL 520 and the first EML 516. That is, the HIL 520 is located between the first electrode 360 and the first EML 516.

[0236] The first transmitting portion 510 may further include a first ETL 518 over the first EML 516 .

[0237] Although not shown, the first transmitting portion 510 may further include at least one of an EBL located between the first HTL 524 and the first EML 516 and an HBL located between the first EML 516 and the first ETL 518. For example, the EML may include a TCTA.

[0238] In the second emission portion 530 , the second HTL 540 is located under the second EML 534 .

[0239] The second transmitting portion 530 may further include a second ETL 536 over the second EML 534 .

[0240] Although not shown, the second transmitting portion 530 may further include at least one of an EBL located between the second HTL 540 and the second EML 534 and an HBL located between the second EML 534 and the second ETL 536. For example, the EML may include a TCTA.

[0241] In the third emission portion 550 , the third HTL 560 is located under the third EML 552 .

[0242] The third emission portion 550 may further include an EIL 556 over the third EML 552 and a third ETL 554 between the third EML 552 and the EIL 556 .

[0243] Although not shown, the third emission portion 550 may further include at least one of an EBL located between the third HTL 560 and the third EML 552 and an HBL located between the third EML 552 and the third ETL 554. For example, the EML may include a TCTA.

[0244] Each of the first EML 516 and the third EML 552 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. In addition, 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.

[0245] In each of the first EML 516 and the third EML 552 that provide light having a wavelength in the range of approximately 440 to 480 nm, 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 552, the host may be 9,10-di(naphthalene-2-yl)anthracene, and the dopant may be 1,6-bis(diphenylamino)pyrene.

[0246] In the second EML 534 that provides light having a wavelength in the range of approximately 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 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).

[0247] 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 540, and the first p-type CGL 574 is located between the first n-type CGL 572 and the second HTL 540.

[0248] 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 536 and the third HTL 560, and the second p-type CGL 584 is located between the second n-type CGL 582 and the third HTL 560.

[0249] 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 540, and the holes are transported to the second EML 534 through the second HTL 540.

[0250] The second n-type CGL 582 provides electrons to the second ETL 536, and the electrons are transported to the second EML 534 through the second ETL 536. The second p-type CGL 584 provides holes to the third HTL 560, and the holes are transported to the third EML 552 through the third HTL 560.

[0251] Therefore, in the OLED D having a triple-stack (three-layer overlap) structure, the driving voltage is reduced and the emission efficiency is improved.

[0252] 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.

[0253] 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. For example, the HIL 520 may include the organic compound of Formula 1-1 as the hole injection material 522. The first p-type CGL 574 may include the organic compound of Formula 1-1 as the first p-type charge generation material 576, and the second p-type CGL 584 may include the organic compound of Formula 1-1 as the second p-type charge generation material 586.

[0254] The hole injection material 522 in the HIL 520 , and 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 may be the same or different.

[0255] The HIL 520 may have a When the HIL 520 includes the organic compound of Formula 1-1 as the hole injection material 522, the HIL 520 may further include a hole injection host material (not shown). That is, the HIL 520 may be formed only of the hole injection material 522 that is the organic compound of Formula 1-1, or may be formed of a mixture of the hole injection material 522 and a hole injection host material.

[0256] The hole injection host material may be NPD. In this case, the hole injection material 522 may have about 1-40 wt%, preferably about 5-20 wt%, in the HIL 520.

[0257] Each of the first p-type CGL 574 and the second p-type CGL 584 may have a thickness of about 100 to 100 mm. When the first p-type CGL 574 and the second p-type CGL 584 include the organic compound of Formula 1-1 as the first p-type charge generation material 576 and the second p-type charge generation material 586, respectively, each of the first p-type CGL 574 and the second p-type CGL 584 may further include a p-type charge generation host material (not shown). That is, the first p-type CGL 574 may be formed only of the first p-type charge generation material 576, which is the organic compound of Formula 1-1, or may be formed of a mixture of the first p-type charge generation material 576 and the p-type charge generation host material. The second p-type CGL 584 may be formed only of the second p-type charge generation material 586, which is the organic compound of Formula 1-1, or may be formed of a mixture of the second p-type charge generation material 586 and the p-type charge generation host material.

[0258] For example, the p-type charge generation host material may be NPD. In this case, in each of the first p-type CGL 574 and the second p-type CGL 584, each of the first charge generation material 576 and the second charge generation material 586 may have about 1-40 wt%, preferably about 10-30 wt%.

[0259] When the HIL 520 includes the hole injection host material and the hole injection material 522 in Formula 1-1, the first p-type CGL 574 includes the p-type charge generation host material and the first p-type charge generation material 576, and the second p-type CGL 584 includes the p-type charge generation host material and the second p-type charge generation material 586, the weight percentage of each of the first p-type charge generation material 576 and the second p-type charge generation material 586 in each of the first p-type CGL 574 and the second p-type CGL 584 can be equal to or greater than the weight percentage of the hole injection material 522 in the HIL 520.

[0260] At least one of the first to third HTLs 524 , 540 , and 560 includes at least one of a first hole transport material that is an organic compound in Formula 2 and a second hole transport material that is an organic compound in Formula 3.

[0261] For example, the first HTL 524 may include at least one of a first hole transport material 526 of an organic compound of Formula 2 and a second hole transport material 528 of an organic compound of Formula 3, the second HTL 540 may include at least one of a first hole transport material 542 of an organic compound of Formula 2 and a second hole transport material 544 of an organic compound of Formula 3, and the third HTL 560 may include at least one of a first hole transport material 562 of an organic compound of Formula 2 and a second hole transport material 564 of an organic compound of Formula 3.

[0262] That is, the first HTL 524 may be formed of only the first hole transport material 526, may be formed of only the second hole transport material 528, or may be formed of a mixture of the first hole transport material 526 and the second hole transport material 528. The second HTL 540 may be formed of only the first hole transport material 542, may be formed of only the second hole transport material 544, or may be formed of a mixture of the first hole transport material 542 and the second hole transport material 544. The third HTL 560 may be formed of only the first hole transport material 562, may be formed of only the second hole transport material 564, or may be formed of a mixture of the first hole transport material 562 and the second hole transport material 564.

[0263] When the first hole transport material 526 and the second hole transport material 528 are included in the first HTL 524, the first hole transport material 542 and the second hole transport material 544 are included in the second HTL 540, and the first hole transport material 562 and the second hole transport material 564 are included in the third HTL 560, the first hole transport material 526 has a first weight percentage in the first HTL 524, and the first hole transport material 542 has a second weight percentage less than the first weight percentage in the second HTL 540. In addition, the first hole transport material 562 has a third weight percentage less than the first weight percentage in the third HTL 560. In other words, each of the weight percentage of the second hole transport material 544 in the second HTL 540 and the weight percentage of the second hole transport material 564 in the third HTL 560 can be greater than the weight percentage of the second hole transport material 528 in the first HTL 524. Therefore, the emission regions in the second and third EMLs 534 and 552 may be present at the centers of the second and third EMLs 534 and 552, and the emission efficiency and lifetime of the OLED D may be improved.

[0264] The thickness of the first HTL 524 may be greater than the thickness of each of the second HTL 540 and the third HTL 560. For example, the first HTL 524 may have a thickness of about 500 to 1000 mm. Thickness, preferably And each of the second HTL 540 and the third HTL 560 may have a thickness of about 200 to Thickness, preferably

[0265] The OLED D includes a first emission part 510 and a third emission part 550, each having a wavelength range of 440 to 480 nm, and a second emission part 530 having a wavelength range of 500 to 550 nm, and provides white light emission, and a first CGL 570 and a second CGL 580 are respectively disposed between the first emission part 510 and the second emission part 530 and between the second emission part 530 and the third emission part 550. Therefore, the OLED D has advantages in driving voltage, emission efficiency, and lifespan.

[0266] refer to Figure 4 , a second electrode 364 is formed on the first substrate 310 in which the organic emission layer 362 is formed.

[0267] 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.

[0268] The first electrode 360 , the organic light emitting layer 362 , and the second electrode 364 constitute an OLED D.

[0269] 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.

[0270] 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.

[0271] 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.

[0272] 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.

[0273] 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.

[0274] 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.

[0275] A color conversion layer may be included instead of the color filter layer 380 .

[0276] 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.

[0277] 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.

[0278] 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 HTL includes the organic compound of Formula 2 and the organic compound of Formula 3. Therefore, hole injection / transport performance toward the EML is improved. Consequently, 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.

[0279] [OLED]

[0280] On the anode (ITO), HIL (HIL, )、HTL(HTL, )、EBL(EBL, TCTA)、EML(EML, Host (9,10-di(naphthalene-2-yl)anthracene) and dopant (1,6-bis(diphenylamino)pyrene, 3 wt%)), ETL (ETL, 1,3,5-Tris(m-pyridin-3-ylphenyl)benzene (TmPyPB)), EIL (LiF, ) and cathode (Al, ) to form an OLED.

[0281] 1. Comparative Example

[0282] (1) Comparative Example 1 (Ref 1)

[0283] The HIL was formed with NPD and HATCN (10 wt %), and the HTL was formed with NPD.

[0284] (2) Comparative Example 2 (Ref2)

[0285] The HIL was formed using NPD and HATCN (10 wt %), and the HTL was formed using compound HO1 in Formula 5.

[0286] (3) Comparative Example 3 (Ref3)

[0287] The HIL was formed using NPD and HATCN (10 wt %), and the HTL was formed using compound H33 in Formula 6.

[0288] (4) Comparative Example 4 (Ref4)

[0289] The HIL was formed using NPD and HATCN (10 wt %), and the HTL was formed using compound H01 in Formula 5 (50 wt %) and compound H33 in Formula 6 (50 wt %).

[0290] 2. Examples

[0291] (1) Example 1 (Ex1)

[0292] The HIL was formed using NPD and compound S07 (10 wt %) in Formula 5, and the HTL was formed using compound H01 in Formula 5.

[0293] (2) Example 2 (Ex2)

[0294] The HIL was formed using NPD and compound S07 (10 wt %) in Formula 5, and the HTL was formed using compound H33 in Formula 6.

[0295] (3) Example 3 (Ex3)

[0296] The HIL was formed using NPD and compound S07 in Formula 5 (10 wt %), and the HTL was formed using compound H01 in Formula 5 (50 wt %) and compound H33 in Formula 6 (50 wt %).

[0297] (4) Example 4 (Ex4)

[0298] The HIL was formed using NPD and compound S20 (10 wt %) in Formula 5, and the HTL was formed using compound H01 in Formula 5.

[0299] (5) Example 5 (Ex5)

[0300] The HIL was formed using NPD and compound S20 (10 wt %) in Formula 5, and the HTL was formed using compound H33 in Formula 6.

[0301] (6) Example 6 (Ex6)

[0302] The HIL was formed using NPD and compound S20 in Formula 5 (10 wt %), and the HTL was formed using compound H01 in Formula 5 (50 wt %) and compound H33 in Formula 6 (50 wt %).

[0303] (7) Example 7 (Ex7)

[0304] The HIL was formed using NPD and compound A13 (10 wt %) in Formula 5, and the HTL was formed using compound H01 in Formula 5.

[0305] (8) Example 8 (Ex8)

[0306] The HIL was formed using NPD and compound A13 (10 wt %) in Formula 5, and the HTL was formed using compound H33 in Formula 6.

[0307] (9) Example 9 (Ex9)

[0308] The HIL was formed using NPD and compound A13 in Formula 5 (10 wt %), and the HTL was formed using compound H01 in Formula 5 (50 wt %) and compound H33 in Formula 6 (50 wt %).

[0309] (10) Example 10 (Ex10)

[0310] The HIL was formed using NPD and compound A13 in Formula 5 (10 wt %), and the HTL was formed using compound H15 in Formula 5 (50 wt %) and compound H26 in Formula 6 (50 wt %).

[0311] 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.

[0312] Table 1

[0313]

[0314] Table 2

[0315] 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 H01 -5.46 -2.19 H15 -5.38 -2.12 H26 -5.51 -2.25 H33 -5.59 -2.28 TCTA -5.80 -2.26

[0316] As shown in Table 1, compared to the OLED of Ref1, which uses NPD to form the HTL, the OLEDs of Ref2 to Ref4, which use the organic compounds of Formula 2 and / or Formula 3 to form the HTL, still have limitations in terms of driving voltage, emission efficiency, and lifespan. That is, even though the organic compounds of Formula 2 and / or Formula 3 are used in the HTL, the energy levels of the HIL and HTL do not match, resulting in performance limitations for the OLEDs of Ref2 to Ref4.

[0317] On the other hand, in the OLEDs of Ex1 to Ex10, the compound of Formula 1-1 (i.e., compound S07, compound S20, or compound A13) is used in the HIL, and at least one of the compound of Formula 2 (i.e., compound H01 or compound H15) and the compound of Formula 3 (i.e., compound H26 or compound H33) is used in the HTL, and the driving voltage is significantly reduced, and the emission efficiency and lifetime are significantly increased.

[0318] Furthermore, in the OLEDs of Ex3, Ex6, Ex9, and Ex10, in which the compound of Formula 2 and the compound of Formula 3 were included in the HTL, the driving voltage was further reduced, and the emission efficiency and lifetime were further increased. Furthermore, in the OLEDs of Ex7 to Ex10, in which the indacene derivative having an asymmetric structure was included in the p-type CGL, the driving voltage was significantly reduced, and the emission efficiency and lifetime were significantly increased.

[0319] 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 being located between the first electrode and the second electrode and comprising a first emission material layer, a hole injection layer located between the first electrode and the first emission material layer, and a first hole transport layer located between the hole injection layer and the first emission material layer; The hole injection layer includes a hole injection material, and the hole injection material is an organic compound represented by Formula 1-4: [Formula 1-4] 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 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, and ii) X2 is different from Y2 and Y3, or X3 is different from Y2 and Y3, The first hole transport layer includes at least one of a first hole transport material shown in Formula 2 and a second hole transport material shown 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, 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.

2. The organic light emitting diode according to claim 1, wherein the hole injection material is one of the compounds of Formula 4: [Formula 4] 3. The organic light emitting diode according to claim 1, wherein the hole injection layer further comprises a hole injection host material, and the hole injection host material is one of the following: 4,4',4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (NATA), 4,4',4"-tris(N-(naphthalene-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazolyl-9-yl-phenyl)amine (TCT A), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4"-diamine (NPD), 1,4,5,8,9,11-hexaazatriphenylene hexacarbonitrile (dipyrazino[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene) polystyrene sulfonate (PEDOT / PSS), and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine.

4. The organic light emitting diode according to claim 1, wherein the first hole transport material is one of the compounds of Formula 5: [Formula 5] 5. The organic light emitting diode according to claim 1, wherein the second hole transport material is one of the compounds of Formula 6: [Formula 6] The organic light emitting diode according to claim 1 , wherein: The first hole transport layer includes the first hole transport material and the second hole transport material, and the first hole transport material and the second hole transport material have the same weight percentage.

7. The organic light emitting diode according to claim 1, further comprising: a second emitting portion comprising a second emitting material layer and a second hole transport 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 is located between the first emission portion and the second emission portion. 8 . The organic light emitting diode according to claim 7 , wherein the second hole transport layer comprises at least one of the first hole transport material and the second hole transport material.

9. The organic light emitting diode according to claim 8, wherein: The second hole transport layer includes the first hole transport material and the second hole transport material, and the first hole transport material and the second hole transport material in the second hole transport layer have the same weight percentage. 10 . The organic light emitting diode according to claim 7 , wherein the first p-type charge generation material is a compound of Formula 1-4.

11. The organic light emitting diode according to claim 7, 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.

12. The organic light emitting diode according to claim 7, further comprising: a third emission portion comprising a third emission material layer and a third hole transport layer, and located between the second emission portion and the second electrode; and A second p-type charge generation layer includes a second p-type charge generation material and is located between the second emission portion and the third emission portion. 13 . The organic light emitting diode according to claim 12 , wherein the third hole transport layer comprises at least one of the first hole transport material and the second hole transport material. 14 . The organic light emitting diode according to claim 13 , wherein the third hole transport layer comprises the first hole transport material and the second hole transport material, and the first hole transport material and the second hole transport material in the third hole transport layer have the same weight percentage. 15 . The organic light emitting diode according to claim 12 , wherein the second p-type charge generating material is an organic compound of Formula 1-4.

16. The organic light emitting diode according to claim 12, 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.

17. 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.

18. The organic light-emitting device according to claim 17, 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 a red pixel, a green pixel, and a blue pixel.

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