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

Abstract

The present disclosure relates to an organic compound represented by a general formula, an organic light emitting diode including the organic compound, and an organic light emitting display device. In the general formula, X is oxygen (O) or sulfur (S), and R1 to R4 are independently selected from hydrogen, deuterium, halogen, cyano, deuterated or undeuterated C1-C10 alkyl, deuterated or undeuterated C1-C10 alkoxy, deuterated or undeuterated C3-C30 cycloalkyl, deuterated or undeuterated C6-C30 aryl, deuterated or undeuterated C6-C30 arylamino and a deuterated or undeuterated C5-C30 heteroaryl group, wherein L1 and L2 are each independently selected from the group consisting of a deuterated or undeuterated C6-C30 arylene group and a deuterated or undeuterated C5-C30 heteroarylene group, wherein a and b are each independently 0 or 1, c and f are each independently an integer of 0-3, and d and e are each independently an integer of 0-2.

Description

Technical Field

[0001] The present invention relates to an organic compound, and more particularly, to an organic compound having improved electron transport efficiency, an organic light emitting diode, and an organic light emitting display device including the organic compound and the organic light emitting diode. Background Art

[0002] As demand for flat panel display devices having a small footprint increases, an organic light emitting display device, which is referred to as an organic electroluminescent device (OELD), including an organic light emitting diode (OLED) in a flat panel display device has been the subject of recent research and development.

[0003] The OLED combines electrons with holes, generates excitons, and converts the excitons from an excited state to a ground state by injecting electrons from a cathode as an electron injection electrode and holes from an anode as a hole injection electrode into a light-emitting material layer (EML). A flexible substrate, such as a plastic substrate, can be used as a base substrate for forming an element. In addition, an organic light-emitting display device can be operated at a voltage (e.g., 10V or less) lower than the voltage required to operate other display devices. In addition, an organic light-emitting display device has advantages in power consumption and color purity.

[0004] In order to provide OLEDs with sufficient luminous efficiency and lifespan, it is necessary to develop electron transport materials with sufficient electron transport efficiency. Summary of the invention

[0005] Technical issues

[0006] Accordingly, the present invention is directed to an organic compound, an OLED, and an organic light emitting device that substantially obviate one or more problems due to limitations and disadvantages of the related art.

[0007] An object of the present invention is to provide an organic compound having improved electron transport efficiency.

[0008] Another object of the present invention is to provide an OLED and an organic light emitting display device including the organic compound and having improved luminous efficiency and lifespan and reduced driving voltage.

[0009] Additional features and advantages of the present invention will be described in the following description, and part of them will be obvious from the description, or can be understood through the practice of the present invention. The purpose and other advantages of the present invention will be realized and obtained through the structures particularly pointed out in the written description and its claims and the drawings.

[0010] Technical Solution

[0011] According to one aspect, the present invention provides an organic compound having the general formula, wherein X is oxygen (O) or sulfur (S), and R1 to R4 are independently selected from hydrogen, deuterium, halogen, cyano, deuterated or undeuterated C1-C10 alkyl, deuterated or undeuterated C1-C10 alkoxy, deuterated or undeuterated C3-C30 cycloalkyl, deuterated or undeuterated C6-C30 aryl, deuterated or undeuterated C6-C30 arylamino and deuterated or undeuterated C5-C30 heteroaryl, L1 and L2 are each independently selected from deuterated or undeuterated C6-C30 arylene and deuterated or undeuterated C5-C30 heteroarylene, a and b are each independently 0 or 1, c and f are each independently an integer of 0-3, and d and e are each independently an integer of 0-2.

[0012]

[0013] According to another aspect, the present invention provides an organic light emitting diode, comprising a first electrode, a second electrode facing the first electrode, and a first light emitting portion comprising a first light emitting material layer and a first electron transport layer and located between the first and second electrodes, wherein the first electron transport layer comprises a first electron transport material and is located between the first light emitting material layer and the second electrode, the first electron transport material is an organic compound of the general formula, wherein X is oxygen (O) or sulfur (S), and R1 to R4 are each independently selected from hydrogen, deuterium, halogen, cyano, deuterated or undeuterated C1-C10 alkyl , a deuterated or undeuterated C1-C10 alkoxy, a deuterated or undeuterated C3-C30 cycloalkyl, a deuterated or undeuterated C6-C30 aryl, a deuterated or undeuterated C6-C30 arylamino and a deuterated or undeuterated C5-C30 heteroaryl, L1 and L2 are each independently selected from a deuterated or undeuterated C6-C30 arylene group and a deuterated or undeuterated C5-C30 heteroarylene group, a and b are each independently 0 or 1, c and f are each independently an integer of 0-3, and d and e are each independently an integer of typically 0-2.

[0014]

[0015] According to another aspect, the present invention provides an organic light emitting diode, comprising a first electrode, a second electrode facing the first electrode, a first light emitting portion comprising a first light emitting material layer and located between the first and second electrodes, a second light emitting portion comprising a second light emitting material layer and located between the first light emitting portion and the second electrode; and a first n-type charge generating layer comprising a first n-type charge generating material and located between the first and second light emitting portions, wherein the first n-type charge generating material is an organic compound of the general formula, wherein X is oxygen (O) or sulfur (S), and R1 to R4 are each independently selected from hydrogen, deuterium, halogen, cyano, deuterated or an undeuterated C1 to C10 alkyl group, a deuterated or undeuterated C1-C10 alkoxy group, a deuterated or undeuterated C3-C30 cycloalkyl group, a deuterated or undeuterated C6-C30 aryl group, a deuterated or undeuterated C6-C30 arylamino group and a deuterated or undeuterated C5-C30 heteroaryl group, L1 and L2 are each independently selected from a deuterated or undeuterated C6-C30 arylene group and a deuterated or undeuterated C5-C30 heteroarylene group, a and b are each independently 0 or 1, c and f are each independently an integer of 0-3, and d and e are each independently an integer of 0-2.

[0016]

[0017] According to another aspect, the present invention provides an organic light emitting display device, including a substrate, the organic light emitting diode located above the substrate; and a packaging film covering the organic light emitting diode.

[0018] 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 invention as claimed.

[0019] Beneficial Effects

[0020] The organic compound of the present invention has a structure in which a thiophene group or a furan group is connected to a phenanthroline moiety directly or through a bond to provide high electron transport efficiency.

[0021] The organic compound of the present invention is included in (or used for) an electron transport layer and / or an n-type charge generation layer of an OLED, so that the OLED and the organic light-emitting device have improved luminous efficiency and lifespan and reduced driving voltage. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] The accompanying drawings are included to provide a further understanding of the invention and are incorporated in and constitute a part of this invention, illustrate embodiments of the invention and together with the description serve to explain the principle of the invention.

[0023] Figure 1 is a circuit diagram showing an organic light emitting display device of the present invention.

[0024] Figure 2 FIG. 4 is a schematic cross-sectional view showing an organic light emitting display device according to a first embodiment of the present invention.

[0025] Figure 3 is a schematic cross-sectional view showing an OLED according to a second embodiment of the present invention.

[0026] Figure 4 is a schematic cross-sectional view showing an organic light emitting display device according to a third embodiment of the present invention.

[0027] Figure 5 is a schematic cross-sectional view showing an OLED according to a fourth embodiment of the present invention.

[0028] Figure 6 is a schematic cross-sectional view showing an OLED according to a fifth embodiment of the present invention. DETAILED DESCRIPTION

[0029] Reference will now be made hereinafter in detail to various aspects of the present invention, examples of which are illustrated in the accompanying drawings.

[0030] The present invention provides a novel organic compound, an OLED containing the organic compound in an electron transport layer and / or an n-type charge generation layer, and an organic light-emitting device containing the OLED. For example, the organic light-emitting device may be an organic light-emitting display device or an organic light-emitting device. As an example, an organic light-emitting display device including the OLED display device of the present invention will be mainly described.

[0031] Figure 1 is a circuit diagram showing an organic light emitting display device of the present invention.

[0032] like Figure 1 As shown, the organic light emitting display device includes a gate line GL, a data line DL, a power line PL, a switching thin film transistor TFT Ts, a driving TFT Td, a storage capacitor Cst, and an OLED D. The gate line GL and the data line DL cross each other to define a pixel region P. The pixel region P may include a red pixel region, a green pixel region, and a blue pixel region.

[0033] The switching TFT Ts is connected to the gate line GL and the data line DL, and the driving TFT Td and the storage capacitor Cst are connected to the switching TFT Ts and the power line PL. The OLED D is connected to the driving TFT Td.

[0034] In the organic light emitting display device, when the switching TFT Ts is turned on by the gate signal applied from the gate line GL, the data signal from the data line DL is applied to the gate electrode of the driving TFT Td and the electrode of the storage capacitor Cst.

[0035] When the driving TFT Td is turned on by the data signal, current is supplied from the power line PL to the OLED D. Therefore, the OLED D emits light. In this case, when the driving TFT Td is turned on, the current level applied from the power line PL to the OLED D is determined so that the OLED D can generate grayscale.

[0036] When the switching TFT Ts is turned off, the storage capacitor Cst is used to maintain the voltage of the gate electrode of the driving TFT Td. Therefore, even if the switching TFT Ts is turned off, the current level applied from the power line PL to the OLED D is maintained until the next frame.

[0037] Therefore, the organic light emitting display device displays a desired image.

[0038] Figure 2 FIG. 4 is a schematic cross-sectional view showing an organic light emitting display device according to a first embodiment of the present invention.

[0039] like Figure 2 As shown, the organic light emitting display device 100 includes a substrate 110, a TFT Tr above the substrate 110, and an OLED D on a planarization layer and connected to the TFT Tr. For example, a red pixel region, a green pixel region, and a blue pixel region may be defined on the substrate 110, and the OLED D is located in each pixel region. That is, the OLED D emitting red, green, and blue light, respectively, may be disposed in the red pixel region, the green pixel region, and the blue pixel region.

[0040] 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.

[0041] A buffer layer 120 is formed on the substrate, and the TFT Tr is formed on the buffer layer 120. The buffer layer 120 may be omitted.

[0042] The semiconductor layer 122 is formed on the buffer layer 120. The semiconductor layer 122 may include an oxide semiconductor material or polysilicon.

[0043] When the semiconductor layer 122 includes an oxide semiconductor material, a light shielding pattern (not shown) may be formed under the semiconductor layer 122. Light reaching the semiconductor layer 122 is shielded or blocked by the light shielding pattern to prevent thermal degradation of the semiconductor layer 122. On the other hand, when the semiconductor layer 122 includes polysilicon, impurities may be doped into both sides of the semiconductor layer 122.

[0044] 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.

[0045] The gate electrode 130 formed of a conductive material such as metal is formed on the gate insulating layer 124 to correspond to the center of the semiconductor layer 122 .

[0046] 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.

[0047] 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.

[0048] 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 at both sides of the gate 130 to be spaced apart from the gate 130.

[0049] The first contact hole 134 and the second contact hole 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 contact hole 134 and the second contact hole 136 are formed only through the interlayer insulating layer 132.

[0050] A source electrode 140 and a drain electrode 142 formed of a conductive material such as metal are formed on the interlayer insulating layer 132 .

[0051] The source electrode 140 and the drain electrode 142 are spaced apart from each other relative to the gate electrode 130 and contact two sides of the semiconductor layer 122 through the first contact hole 134 and the second contact hole 136 , respectively.

[0052] The semiconductor layer 122, the gate electrode 130, the source electrode 140, and the drain electrode 142 constitute the TFT Tr. The TFT Tr functions as a driving element. That is, the TFT Tr functions as a driving element.

[0053] 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 planar structure.

[0054] 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.

[0055] Although not shown, the gate line and the data line cross each other to define a pixel region, and the switching TFT is formed to be connected to the gate line and the data line. The switching TFT is connected to a TFT Tr as a driving element.

[0056] 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 gate voltage of the TFT Tr in one frame may be further formed.

[0057] The planarization layer 150 is formed on the entire surface of the substrate 110 to cover the TFT Tr. The planarization layer 150 has a drain contact hole 152 exposing the drain electrode 142 of the TFT Tr.

[0058] The first electrode 160 is disposed on the planarization layer 150 and is formed in each pixel region, respectively. The first electrode 160 is connected to the drain electrode 142 of the TFT Tr through the drain contact hole 152 .

[0059] 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 oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium copper oxide (ICO) or aluminum zinc oxide (Al:ZnO, AZO).

[0060] 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 material layer. When the organic light-emitting display device 100 operates in a top emission mode, a reflective electrode or a reflective layer may be formed below the first electrode 160. For example, the reflective electrode or the 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.

[0061] In addition, a 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 area and exposes the center of the first electrode 160 in the pixel area.

[0062] The organic light emitting layer 162 as a light emitting unit is formed on the first electrode 160. The organic light emitting layer 162 may include a light emitting material layer (EML) containing a light emitting material and an electron transport layer (ETL) on or above the EML. In addition, the organic light emitting layer 162 may also include a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a hole blocking layer (HBL) and an electron injection layer (EIL) At least one. As described below, the ETL includes an organic compound having a structure in which a thiophene group or a furan group is directly or through a bond connected to a phenanthroline portion, so that electrons are effectively transferred to the EML through the ETL.

[0063] The second electrode 164 is formed above the substrate 110 on which the organic light emitting layer 162 is formed. The second electrode 164 covers the entire surface of the display area and may be formed of a conductive material having a relatively low work function to serve as a cathode. For example, the second electrode 164 may be formed of aluminum (Al), magnesium (Mg), silver (Ag), or alloys thereof such as Al-Mg alloy (AlMg) or Ag-Mg alloy (MgAg). In the top emission type organic light emitting display device 100, the second electrode 164 may have a thin profile (small thickness) to provide light-transmitting properties (or semi-light-transmitting properties).

[0064] 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.

[0065] The first electrode 160 , the organic light emitting layer 162 and the second electrode 164 constitute an OLED D.

[0066] An encapsulation film (or encapsulation layer) 170 is formed on the second electrode 164 to prevent moisture from penetrating into the OLED D. The encapsulation film 170 includes a first inorganic insulating layer 172, an organic insulating layer 174, and a second inorganic insulating layer 176 sequentially stacked, but is not limited thereto. The encapsulation film 170 may be omitted.

[0067] The organic light-emitting display device 100 may include a color filter layer (not shown). The color filter layer may include red, green, and blue color filters corresponding to red, green, and blue pixel regions, respectively. The color purity of the organic light-emitting display device 100 may be improved by the color filter layer.

[0068] The organic light-emitting display device 100 may further include a polarizing plate (not shown) for reducing ambient light reflection. For example, the polarizing plate may be a circular polarizing plate. In a bottom-emission organic light-emitting display device 100, the polarizing plate may be disposed below the substrate 110. In a top-emission organic light-emitting display device 100, the polarizing plate may be disposed on or above the encapsulation film 170.

[0069] In addition, in the top emission type organic light emitting display device 100, a cover window (not shown) may be attached to the packaging film 170 or the polarizing plate. In this case, the substrate 110 and the cover window have flexible characteristics, so that a flexible organic light emitting display device can be provided.

[0070] Figure 3 is a schematic cross-sectional view showing an OLED according to a second embodiment of the present invention.

[0071] like Figure 3 As shown, the OLED D1 includes the first electrode 160 and the second electrode 164 facing each other, and the organic light emitting layer 162 therebetween. The organic light emitting layer 162 includes an EML 240 between the first electrode 160 and the second electrode 164 and an ETL 250 between the second electrode 164 and the EML 240.

[0072] The first electrode 210 may be an anode, and the second electrode 230 may be a cathode. 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.

[0073] Holes are provided from the first electrode 160 into or toward the EML 240 , and electrons are provided from the second electrode 160 into or toward the EML 240 through the ETL 250 .

[0074] The organic light emitting layer 162 may further include a HTL 220 between the first electrode 160 and the EML 240 .

[0075] In addition, the organic light emitting layer 162 may further include at least one of a HIL 210 between the first electrode 160 and the HTL 220 and an EIL 260 between the second electrode 164 and the ETL 250 .

[0076] Although not shown, the organic light emitting layer 162 may further include at least one of an EBL between the HTL 220 and the EML 240 and an HBL between the EML 240 and the ETL 250 .

[0077] For example, the HIL 210 may include a phthalocyanine (CuPc), tris(4-carbazol-9-yl-phenyl)amine (TCTA), N,N'-biphenyl-N,N'-di(1-naphthyl)-1,1'-biphenyl-4,1 ... At least one compound selected from the group consisting of 4"-diamine (NPB; NPD), 1,4,5,8,9,11-hexaazatriphenylene hexacarbonitrile (dipyrazine [2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile; HAT-CN), 1,3,5-tris[4-(biphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene)polystyrenesulfonic acid (PEDOT / PSS) and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, but not limited thereto.

[0078] The HTL 220 may include a material selected from the group consisting of N,N'-biphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), NPB (NPD), 4,4'-di(N-carbazolyl)-1,1'-biphenyl (CBP), poly[N,N'-di(4-butylphenyl)-N,N'-di(phenyl)-benzidine] (poly-TPD), poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))] (TFB ), di[4-(N,N-di-p-tolyl-amino)-phenyl]cyclohexane (TAPC), 3,5-di(9H-carbazole-9-yl)-N,N-diphenylamine (DCDPA), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, and N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)biphenyl-4-amine, but is not limited thereto.

[0079] The EBL may include at least one compound selected from the group consisting of TCTA, tris[4-(diethylamino)phenyl]amine, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, TAPC, MTDATA, 1,3-di(carbazol-9-yl)benzene (mCP), 3,3'-di(N-carbazolyl)-1,1'-biphenyl (mCBP), CuPc, N,N'-bis[4-(bis(3-methylphenyl)amino)phenyl]-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD), TDAPB, DCDPA, and 2,8-bis(9-phenyl-9H-carbazol-3-yl)dibenzo[b,d]thiophene, but is not limited thereto.

[0080] The HBL may include a group consisting of tris-(8-hydroxyquinoline aluminum (Alq3), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, quinoline lithium (Liq), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), bis(2-methyl-8-hydroxyquinoline-N1,08)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 4,7-biphenyl-1,10-phenanthroline (Bphen), 2,9-di(naphthalene-2-yl)-4,7-biphenyl-1,10-phenanthroline (NBphen), 2,9-dimethyl-4,7-biphenyl-1,10-phenanthroline (BCP), 3-(4-biphenyl)-4-phenyl- At least one compound selected from the group consisting of 5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-biphenyl-4H-1,2,4-triazole (NTAZ), 1,3,5-tri(p-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tri(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), poly[9,9-di(3'-((N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene]-cross-2,7-(9,9-dioctylfluorene)] (PFNBr), tris(phenylquinoxaline) (TPQ) and biphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1), but not limited thereto.

[0081] The EIL 260 may include at least one of an alkali metal halide (eg, LiF, CsF, NaF, or BaF 2 ) and an organic metal compound (eg, Liq, lithium benzoate, or sodium stearate), but is not limited thereto.

[0082] The EML 240 in the red pixel region includes a host and a red dopant, the EML 240 in the green pixel region includes a host and a green dopant, and the EML 240 in the blue pixel region includes a host and a blue dopant. Each of the red dopant, the green dopant, and the blue dopant may be independently a fluorescent compound, a phosphorescent compound, or a delayed fluorescent compound.

[0083] For example, in the EML 240 of the red pixel area, the host may be CBP (4,4'-bis(carbazole-9-yl)biphenyl), and the red dopant may be selected from PIQIr(acac) (bis(1-phenylisoquinoline)iridium acetylacetonate), PQIr(acac) (bis(1-phenylquinoline)iridium acetylacetonate), PQIr(tris(1-phenylquinoline)iridium), and PtOEP (octaethylporphyrin platinum), but is not limited thereto. The EML 240 in the red pixel area may have an emission wavelength range of approximately 600 to 650 nm.

[0084] In the EML 240 of the green pixel region, the host may be CBP (4,4'-di(carbazole-9-yl)biphenyl), and the green dopant may be Ir(ppy)3 (fac-tris(2-phenylpyridine)iridium) or Alq3 (tris(8-hydroxyquinoline)aluminum), but are not limited thereto. The EML 240 in the green pixel region may have an emission wavelength range of approximately 510 to 570 nm.

[0085] In the EML 240 of the blue pixel region, the host may be an anthracene derivative, and the blue dopant may be a boron derivative, but is not limited thereto. For example, the host may be a compound of Formula 5, and the blue dopant may be a compound of Formula 6. In the EML 240 in the blue pixel region, the blue dopant may have a weight percentage of about 1 to 20%, preferably about 1 to 10. The EML 240 in the blue pixel region may have an emission wavelength range of about 440 to 480 nm.

[0086] The ETL 250 includes the organic compound of the present invention as the electron transport material 252, which has a structure in which a thiophene group or a furan group is directly or through a bond connected to a phenanthroline moiety. The organic compound of the present invention is represented by Formula 1-1.

[0087] [Formula 1-1]

[0088]

[0089] In Formula 1-1, X is oxygen (O) or sulfur (S), and R1 to R4 are independently selected from hydrogen, deuterium, halogen, cyano, deuterated or undeuterated C1-C10 alkyl, deuterated or undeuterated C1-C10 alkoxy, deuterated or undeuterated C3-C30 cycloalkyl, deuterated or undeuterated C6-C30 aryl, deuterated or undeuterated C L1 and L2 are each independently selected from a deuterated or undeuterated C6-C30 arylamino group and a deuterated or undeuterated C5-C30 heteroaryl group, a and b are each independently 0 or 1, c and f are each independently an integer of 0-3, and d and e are each independently an integer of 0-2.

[0090] For example, the C6-C30 aryl group may be selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, pentenyl, indenyl, indenoindenyl, heptenyl, biphenyl, indacenyl, phenanthrenyl, triphenylenyl, diphenylphenanthrenyl, azulenyl, pyrenyl, fluoranthenyl, triphenylene, chrysenyl, tetraphenyl, tetrasenyl, pyrenyl, pentaphenyl, fused pentaphenyl, fluorenyl, indenofluorenyl and spirofluorenyl, and the C6-C30 arylene group may be their arylene groups.

[0091] The C5-C30 heteroaryl group may be selected from pyrrolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, imidazolyl, pyrazolyl, indolyl, isoindolyl, indazolyl, indolizinyl, pyrrolizinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, quinolyl, isoquinolyl, phthalazinyl, quinoxalinyl, sinolinyl, quinazolinyl, quinozolinyl, quinolyl, purinyl, phthalazinyl, quinoxalinyl, benzoquinolyl, benzoisoquinolyl, benzoquinazolinyl The C5-C30 heteroarylene group may be a heteroarylene group thereof.

[0092] Each of the C1-C10 alkyl group, C1-C10 alkoxy group, C3-C30 cycloalkyl group, C6-C30 aryl group, C6-C30 arylamino group, C5-C30 heteroaryl group, C6-C30 arylene group, and C5-C30 heteroarylene group may be unsubstituted or substituted with deuterium or halogen (eg, fluorine).

[0093] For example, each of R1-R3 can be independently selected from deuterium, fluorine, cyano, methoxy, trifluoromethyl, trifluoromethoxy, methyl, phenyl, pyridyl, naphthyl and quinolyl. Each of R1-R3 can be unsubstituted or substituted with deuterium.

[0094] R4 can be a C6-C30 aryl group. R4 can be selected from phenyl, naphthyl, phenanthrenyl, pyrenyl, anthracenyl and phenylanthracenyl, and f can be an integer of 1-3. For example, f can be 2 or 3, and at least one of R4 can be a polycyclic aryl group, such as phenanthrenyl, pyrenyl, anthracenyl or phenylanthracenyl. Preferably, f can be 3, two of R4 can be phenyl, and another of R4 can be a polycyclic aryl group, such as phenanthrenyl, pyrenyl, anthracenyl or phenylanthracenyl. R4 can be unsubstituted or substituted with deuterium.

[0095] Each of L1 and L2 may be a C6-C30 arylene group, such as a phenylene group or a naphthylene group. For example, each of L1 and L2 may be unsubstituted or substituted with deuterium, a C1-C10 alkyl group, or C-D3. At least one of a and b may be 1.

[0096] For example, each of L1 and L2 can be independently selected from the groups in Formula 1-2.

[0097] [Formula 1-2]

[0098]

[0099] The phenanthroline moiety in Formula 1-1 may be selected from the group in Formula 1-3.

[0100] [Formula 1-3]

[0101]

[0102] The thiophene group in Formula 1-1, ie, X=S, can be selected from the groups in Formula 1-4.

[0103] [Formula 1-4]

[0104]

[0105]

[0106] The furan group in Formula 1-1, ie, X=O, can be selected from the group in Formula 1-5.

[0107] [Formula 1-5]

[0108]

[0109]

[0110] The organic compound of the present invention has a structure in which a thiophene group or a furan group is directly or through a bond connected to a phenanthroline portion to provide high electron transport performance. For example, when in Formula 1-1, the second position of the thiophene group or the furan group is directly or through a bond, i.e., L1 and / or L2, connected (bound or connected) to the phenanthroline portion, and the three hydrogen atoms of the thiophene group or the furan group are replaced by C6-C30 aryl groups, i.e., f=3, the electron transport performance of the organic compound is further improved.

[0111] The organic compound in Formula 1-1 can be represented by Formula 1-6.

[0112] [Formula 1-6]

[0113]

[0114] For example, the organic compound of the present invention may be one of the compounds in Formula 2.

[0115] [Formula 2]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] [synthesis]

[0134] 1. Synthesis of Compound D1

[0135] (1) Intermediate A

[0136] [Reaction formula 1-1]

[0137]

[0138] 1-Bromo-4-acetylnaphthalene (14.5 g, 0.058 mol), 8-aminoquinoline-7-carboxaldehyde (10 g, 0.058 mol), anhydrous EtOH (ethanol, 800 ml) and KOH (potassium hydroxide, 13 g), 0.232 mol) were added to a round-bottom flask and refluxed for 15 hours. The reaction mixture was cooled to room temperature, extracted with CH2Cl2 / H2O and the organic layer was recovered. The organic layer was concentrated under reduced pressure and recrystallized from EtOAc (ethyl acetate) to obtain Intermediate A (10.5 g, 0.027 mol, 47%).

[0139] (2) Intermediate B

[0140] [Reaction 1-2]

[0141]

[0142] Intermediate A (10 g, 0.026 mol), bis(pinacol)diboron (7.9 g, 0.04 mol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.1 g, 0.2 mol), KOAc (potassium acetate, 9.2 g, 0.09 mol) and 1,4-dioxane (200 ml) were added to a round-bottom flask and refluxed for 12 hours. After the reaction solution was cooled to room temperature, it was filtered using celite and washed with CHCl3. The residual solution was concentrated under reduced pressure and recrystallized with EtOAc to obtain Intermediate B (7.9 g, 0.023 mol, 88%).

[0143] (3) Intermediate C

[0144] [Reaction 1-3]

[0145]

[0146] In a round-bottom flask, 2,5-dibromothiophene (10.0 g, 0.041 mol), phenylboronic acid (4.88 g, 0.040 mol), tetrakis(triphenylphosphine)palladium(0) (1.8 g, 0.2 mmol) and K2OC3 (16.6 g, 0.12 mol) were dissolved in a mixed solvent of toluene (150 mL) and EtOH (60 mL) and refluxed for 12 hours. The reaction mixture was cooled to room temperature, and the reaction solution was filtered to obtain a crude product. After the crude product was dissolved in CH2Cl2, the organic solution was dried with MgSO4 and the solvent was removed. The mixture was subjected to silica gel column chromatography (eluent = CHCl3) to obtain intermediate C (8.14 g, 0.034 mol, 85%).

[0147] (4) Compound D1

[0148] [Reaction 1-4]

[0149]

[0150] Intermediate B (7.9 g, 0.022 mol) and Intermediate C were used to obtain Compound D1 (8.38 g, 0.018 mol, 82%) in the same manner as that for the synthesis of Intermediate C.

[0151] 2. Synthesis of Compound D5

[0152] (1) Intermediate D

[0153] [Reaction formula 2-1]

[0154]

[0155] Intermediate D (6.3 g, 0.016 mol, 64%) was obtained by the same method as that of Intermediate C using 2,3,4,5-tetrabromothiophene (10.0 g, 0.025 mol) and phenylboronic acid (9.1 g, 0.075 mol).

[0156] (2) Compound D5

[0157] [Reaction formula 2-2]

[0158]

[0159] Compound D5 (2.94 g, 0.0048 mol, 80%) was obtained by the same method as that for synthesizing Intermediate C using Intermediate B (2.1 g, 0.006 mol) and Intermediate D (2.5 g, 0.064 mol).

[0160] 3. Synthesis of Compound D7

[0161] (1) Intermediate E

[0162] [Reaction formula 3-1]

[0163]

[0164] Compound E (6.3 g, 0.016 mol, 64%) was obtained by the same method as that of Intermediate C using 2,3,4-tribromothiophene (10.0 g, 0.025 mol) and phenylboronic acid (9.1 g, 0.075 mol).

[0165] (2) Intermediate F

[0166] [Reaction formula 3-2]

[0167]

[0168] Intermediate E (6.0 g, 0.019 mol) and N-bromosuccinimide (NBS, 3.7 g, 0.021 mol) were dissolved in CHCl3 (200 mL) and stirred at room temperature for 5 hours. Distilled water (200 mL) was added to the reaction mixture, and Na2S2O3 (5 g) was added while stirring at room temperature, and the mixture was stirred for 1 hour. The reaction mixture was extracted with CH2Cl2 / H2O to recover the organic layer. The organic layer was concentrated under reduced pressure and recrystallized from CH2Cl2 and petroleum ether to obtain Intermediate F (7.1 g, 0.018 mol, 95%).

[0169] (3) Intermediate G

[0170] [Reaction formula 3-3]

[0171]

[0172] Intermediate F (10 g, 0.026 mol), bis(pinacol)diboron (7.8 g, 0.02 mol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.55 g, 0.1 mmol), KOAc (4.6 g, 0.045 mol) and 1,4-dioxane (150 ml) were added and refluxed for 12 hours. The reaction solution was cooled to room temperature, filtered using celite, and washed with CHCl3. The residual solution was concentrated under reduced pressure and recrystallized from hexane to obtain Intermediate G (7.9 g, 0.022 mol, 85%).

[0173] (4) Intermediate H

[0174] [Reaction 3-4]

[0175]

[0176] Compound H (5.1 g, 0.011 mol, 79%) was obtained by the same method as that of Intermediate C using Intermediate G (5.0 g, 0.014 mol) and 1,4-dibromobenzene (6.6 g, 0.028 mol).

[0177] (5) Compound D7

[0178] [Reaction 3-5]

[0179]

[0180] Compound D7 (3.2 g, 4.6 mmol, 87%) was obtained by the same method as that for the synthesis of Intermediate C using Intermediate B (1.9 g, 5.4 mmol) and Intermediate H (2.5 g, 5.3 mmol).

[0181] 4. Synthesis of Compound D23

[0182] (1) Intermediate I

[0183] [Reaction 4-1]

[0184]

[0185] Intermediate I (6.2 g, 14.8 mmol, 79%) was obtained in the same manner as Intermediate C using 2,3,4-tribromothiophene (6.0 g, 18.7 mmol) and phenanthren-9-ylboronic acid (4.2 g, 18.9 mmol).

[0186] (2) Intermediate J

[0187] [Reaction 4-2]

[0188]

[0189] Intermediate J (5.5 g, 13.3 mmol, 90%) was obtained by the same method as that of Intermediate C using Intermediate I (6.2 g, 14.8 mmol) and phenylboronic acid (4.0 g, 32.8 mmol).

[0190] (3) Intermediate L

[0191] [Reaction 4-3]

[0192]

[0193] Intermediate K was obtained by the same method as Intermediate F using Intermediate J (5.5 g, 13.3 mmol), and Intermediate L (4.9 g, 10.7 mmol, 80%) was obtained by the same method as Intermediate G using Intermediate K.

[0194] (4) Intermediate M

[0195] [Reaction formula 4-4]

[0196]

[0197] Intermediate M (3.9 g, 6.9 mmol, 78%) was obtained by the same method as that of Intermediate C using Intermediate L (4.0 g, 8.8 mmol) and 1,4-dibromobenzene (3.0 g, 12.7 mmol).

[0198] (5) Compound D23

[0199] [Reaction 4-5]

[0200]

[0201] Compound D23 (3.8 g, 4.8 mmol, 70%) was obtained by the same method as that for synthesizing Intermediate C using Intermediate B (2.4 g, 6.9 mmol) and Intermediate M (3.9 g, 6.9 mmol).

[0202] 5. Synthesis of Compound D29

[0203] (1) Intermediate N

[0204] [Reaction formula 5-1]

[0205]

[0206] Intermediate N (5.3 g, 10.3 mmol, 69%) was obtained by the same method as that of Intermediate C using 2,3,4-tribromothiophene (4.9 g, 15.3 mmol) and pyrene-1-ylboronic acid (3.7 g, 15.0 mmol).

[0207] (2) Compound D29

[0208] [Reaction formula 5-2]

[0209]

[0210] Compound D29 (5.8 g, 7.8 mmol, 76%) was obtained by the same method as that for synthesizing Intermediate C using Intermediate B (3.7 g, 10.6 mmol) and Intermediate N (5.3 g, 10.3 mmol).

[0211] 6. Synthesis of Compound D38

[0212] (1) Intermediate O

[0213] [Reaction formula 6-1]

[0214]

[0215] Intermediate O (5.2 g, 9.16 mmol, 61%) was obtained by the same method as that of Intermediate K using 2,3,4-tribromothiophene (4.9 g, 15.3 mmol) and 10-phenyl-anthracen-9-ylboronic acid (4.5 g, 15.1 mmol).

[0216] (2) Intermediate P

[0217] [Reaction formula 6-2]

[0218]

[0219] Intermediate P (4.6 g, 8.64 mmol, 94%) was obtained by the same method as that for the synthesis of Intermediate B using Intermediate O (5.2 g, 9.16 mmol).

[0220] (3) Intermediate Q

[0221] [Reaction formula 6-3]

[0222]

[0223] Intermediate Q (5.1 g, 7.9 mmol, 92%) was obtained by the same method as that of Intermediate C using Intermediate P (4.6 g, 8.6 mmol) and 1,3-dibromobenzene (3.0 g, 12.7 mmol).

[0224] (4) Compound D38

[0225] [Reaction 6-4]

[0226]

[0227] Compound D38 (4.2 g, 4.8 mmol, 61%) was obtained by the same method as that for synthesizing Intermediate C using Intermediate B (3.0 g, 8.6 mmol) and Intermediate Q (5.1 g, 7.9 mmol).

[0228] 7. Synthesis of Compound D41

[0229] (1) Intermediate S

[0230] [Reaction formula 7-1]

[0231]

[0232] Intermediate S (8.5 g, 0.038 mol, 86%) was obtained by the same method as that of Intermediate C using 2,5-dibromofuran (10.0 g, 0.044 mol) and phenylboronic acid (6.0 g, 0.049 mol).

[0233] (2) Compound D41

[0234] [Reaction 7-2]

[0235]

[0236] Compound D41 (8.4 g, 0.019 mol, 83%) was obtained by the same method as that for synthesizing Intermediate C using Intermediate B (8.0 g, 0.023 mol) and Intermediate S (6.5 g, 0.029 mol).

[0237] 8. Synthesis of Compound D45

[0238] (1) Intermediate T

[0239] [Reaction formula 8-1]

[0240]

[0241] Intermediate T (4.92 g, 0.0131 mol, 50%) was obtained by the same method as that of Intermediate C using 2,3,4,5-tetrabromofuran (10.0 g, 0.0261 mol) and phenylboronic acid (10.0 g, 0.0820 mol).

[0242] (2) Compound D45

[0243] [Reaction formula 8-2]

[0244]

[0245] Compound D45 (5.20 g, 0.00866 mol, 72%) was obtained by the same method as that for synthesizing Intermediate C using Intermediate B (4.20 g, 0.0120 mol) and Intermediate T (4.92 g, 0.0131 mol).

[0246] 9. Synthesis of Compound D47

[0247] (1) Intermediate U

[0248] [Reaction formula 9-1]

[0249]

[0250] Intermediate U (5.3 g, 0.0117 mol, 36%) was obtained by using 2,3,4-tribromofuran (10.0 g, 0.0328 mol) in the same manner as for synthesizing Intermediate E, Intermediate F, Intermediate G and Intermediate H.

[0251] (2) Compound D47

[0252] [Reaction formula 9-2]

[0253]

[0254] Compound D47 (5.3 g, 0.0078 mol, 65%) was obtained by the same method as that for synthesizing Intermediate C using Intermediate B (4.8 g, 0.014 mol) and Intermediate U (5.3 g, 0.012 mol).

[0255] 10. Synthesis of Compound D63

[0256] (1) Intermediate V

[0257] [Reaction formula 10-1]

[0258]

[0259] Intermediate V (6.82 g, 0.0124 mol, 38%) was obtained by using 2,3,4-tribromofuran (10.0 g, 0.0328 mol) in the same manner as for synthesizing Intermediate I, Intermediate J, Intermediate K, Intermediate L and Intermediate M.

[0260] (2) Compound D63

[0261] [Reaction formula 10-2]

[0262]

[0263] Intermediate B (4.8 g, 0.014 mol) and Intermediate V (6.8 g, 0.012 mol) were used to obtain compound D63 (7.1 g, 0.0091 mol, 76%) in the same manner as that of Intermediate C.

[0264] 11. Synthesis of Compound D69

[0265] (1) Intermediate W

[0266] [Reaction formula 11-1]

[0267]

[0268] Intermediate W (5.7 g, 0.00990 mol, 30%) was obtained by using 2,3,4-tribromofuran (10.0 g, 0.0328 mol) in the same manner as for synthesizing Intermediate I, Intermediate J, Intermediate K, Intermediate L and Intermediate M.

[0269] (2) Compound D69

[0270] [Reaction formula 11-2]

[0271]

[0272] Compound D69 (5.2 g, 0.0072 mol, 72%) was obtained by the same method as that for synthesizing Intermediate C using Intermediate B (4.0 g, 0.011 mol) and Intermediate W (5.7 g, 0.0099 mol).

[0273] 12. Synthesis of Compound D78

[0274] (1) Intermediate X

[0275] [Reaction formula 12-1]

[0276]

[0277]

[0278] Intermediate X (5.2 g, 0.0083 mol, 25%) was obtained by using 2,3,4-tribromofuran (10.0 g, 0.0328 mol) in the same manner as that for synthesizing Intermediate I, Intermediate J, Intermediate K, Intermediate L and Intermediate M.

[0279] (2) Compound D78

[0280] [Reaction 12-2]

[0281]

[0282] Compound D78 (4.8 g, 0.0056 mol, 67%) was obtained by the same method as that for synthesizing Intermediate C using Intermediate B (3.3 g, 0.0094 mol) and Intermediate X (5.2 g, 0.0083 mol).

[0283] In the OLED D, since the ETL 250 includes the electron transport material 252 as the organic compound of the present invention, the electron transport property from the second electrode 164 as the cathode into (or toward) the EML 240 is improved. Therefore, in the OLED D and the organic light emitting display device 100, the driving voltage is reduced, and the light emission efficiency and lifespan are improved.

[0284] [OLED]

[0285] On the anode (ITO), HIL ( Compound of Formula 3), HTL( Compound of Formula 4), EML ( Host (compound of formula 5) and dopant (compound of formula 6), 3wt%), ETL EIL( LiF) and cathode (Al) are stacked in sequence to form an OLED.

[0286] 1. Comparative Example (Ref)

[0287] The ETL is formed by using the compound of Formula 7.

[0288] 2. Example

[0289] (1) Example 1 (Ex1)

[0290] The ETL is formed by using the compound D1 in Formula 2.

[0291] (2) Example 2 (Ex2)

[0292] The ETL is formed by using compound D5 in Formula 2.

[0293] (3) Example 3 (Ex3)

[0294] The ETL is formed by using compound D7 in Formula 2.

[0295] (4) Example 4 (Ex4)

[0296] The ETL is formed by using compound D23 in Formula 2.

[0297] (5) Example 5 (Ex5)

[0298] The ETL is formed by using compound D29 in Formula 2.

[0299] (6) Example 6 (Ex6)

[0300] The ETL is formed by using compound D38 in Formula 2.

[0301] (7) Example 7 (Ex7)

[0302] The ETL is formed by using compound D41 in Formula 2.

[0303] (8) Example 8 (Ex8)

[0304] The ETL is formed by using compound D45 in Formula 2.

[0305] (9) Example 9 (Ex9)

[0306] The ETL is formed by using compound D47 in Formula 2.

[0307] (10) Example 10 (Ex10)

[0308] The ETL is formed by using compound D63 in Formula 2.

[0309] (11) Example 11 (Ex11)

[0310] The ETL is formed by using compound D69 in Formula 2.

[0311] (12)Example 12(Ex12)

[0312] The ETL is formed by using compound D78 in Formula 2.

[0313] [Formula 3]

[0314]

[0315] [Formula 4]

[0316]

[0317] [Formula 5]

[0318]

[0319] [Formula 6]

[0320]

[0321] [Formula 7]

[0322]

[0323] The light emitting characteristics, ie, driving voltage (ΔV), efficiency and lifetime of the OLEDs in Comparative Example and Examples 1 to 12 were measured and are listed in Table 1.

[0324] [Table 1]

[0325] ETL ΔV efficiency lifespan Ref Formula7 0.00 100 100 Ex1 D1 -0.14 99 84 Ex2 D5 -0.14 108 105 Ex3 D7 -0.18 114 113 Ex4 D23 -0.23 110 118 Ex5 D29 -0.28 118 115 Ex6 D38 -0.25 112 109 Ex7 D41 -0.10 88 81 Ex8 D45 -0.13 99 100 Ex9 D47 -0.15 108 110 Ex10 D63 -0.21 113 115 Ex11 D69 -0.22 115 108 Ex12 D78 -0.19 119 114

[0326] As shown in Table 1, compared with the OLED of Ref, the ETL of the OLEDs of Ex1 to Ex12 includes the organic compound of the present invention, which has a structure in which a thiophene group or a furan group is directly or through a bond connected to the phenanthroline part, and the OLEDs have advantages in driving voltage, luminous efficiency and lifespan.

[0327] In addition, compared with Ex1 and Ex7 using organic compounds in which hydrogen is present at the meta-position of the thiophene group or the meta-position of the furan group, the OLEDs of Ex2 to Ex6 using organic compounds in which an aromatic substituent is present at the meta-position of the thiophene group and Ex8 to Ex12 using organic compounds in which an aromatic substituent is present at the meta-position of the furan group have significantly reduced driving voltage and significantly improved luminous efficiency and lifetime.

[0328] In addition, compared with Ex1 to Ex3 OLEDs having only monocyclic aromatic substituents in the thiophene group and Ex7 to Ex9 OLEDs having only monocyclic aromatic substituents in the furan group, in Ex4 to Ex6 OLEDs having polycyclic aromatic substituents in the thiophene group and Ex10 to Ex12 OLEDs having polycyclic aromatic substituents in the furan group, the driving voltage is further reduced, and the luminous efficiency and lifetime are further improved.

[0329] Figure 4 is a schematic cross-sectional view showing an organic light emitting display device according to a third embodiment of the present invention. Figure 5 is a schematic cross-sectional view showing an OLED according to a fourth embodiment of the present invention, and Figure 6 is a schematic cross-sectional view showing an OLED according to a fifth embodiment of the present invention.

[0330] like Figure 4 As shown, the organic light-emitting display device 300 includes a first substrate 310 defining a red pixel area BP, a green pixel area GP, and a blue pixel area BP, 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 between the OLED D and the second substrate 370.

[0331] 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.

[0332] The buffer layer 320 is formed on the substrate, and the TFT Tr corresponding to each of the red pixel RP, the green pixel GP, and the blue pixel BP is formed on the buffer layer 320. The buffer layer 320 may be omitted.

[0333] The semiconductor layer 322 is formed on the buffer layer 320. The semiconductor layer 322 may include an oxide semiconductor material or polysilicon.

[0334] 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.

[0335] A gate electrode 330 formed of a conductive material such as metal is formed on the gate insulating layer 324 to correspond to the center of the semiconductor layer 322 .

[0336] 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.

[0337] The interlayer insulating layer 332 includes a first contact hole 334 and a second contact hole 336 exposing both ends of the semiconductor layer 322. The first contact hole 334 and the second contact hole 336 are located at both sides of the gate 330 to be spaced apart from the gate 330.

[0338] A source electrode 340 and a drain electrode 342 formed of a conductive material such as metal are formed on the interlayer insulating layer 332 .

[0339] The source electrode 340 and the drain electrode 342 are spaced apart from each other relative to the gate electrode 330 and contact two ends of the semiconductor layer 322 through the first contact hole 334 and the second contact hole 336 , respectively.

[0340] The semiconductor layer 322, the gate electrode 330, the source electrode 340, and the drain electrode 342 constitute the TFT Tr. The TFT Tr is used as a driving element. That is, the TFT Tr may correspond to the driving TFT Td ( Figure 1 ).

[0341] Although not shown, the gate lines and the data lines cross each other to define pixels, and the switching TFT is formed to be connected to the gate lines and the data lines. The switching TFT is connected to the TFT Tr as a driving element.

[0342] 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 gate voltage of the TFT Tr in one frame may be further formed.

[0343] A planarization layer 350 including a drain contact hole 352 exposing the drain electrode 342 of the TFT Tr is formed to cover the TFT Tr.

[0344] The 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 planar layer 350, respectively. 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 also 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 type organic light emitting display device 300, the first electrode 160 may have a three-layer structure of ITO / Ag / ITO or ITO / APC / ITO.

[0345] A bank layer 366 is formed on the planarization layer 350 to cover the edge of the first electrode 360. That is, the bank layer 366 is located at the boundary of the pixel area and exposes the center of the first electrode 360 ​​in the pixel area. Since the OLED D emits white light in the red pixel RP, the green pixel GP, and the blue pixel BP, the organic light emitting layer 362 may be formed as a common layer in the red pixel RP, the green pixel GP, and the blue pixel BP without separation. The bank layer 366 is formed to prevent current leakage at the edge of the first electrode 360 ​​and may be omitted.

[0346] The organic light emitting layer 362 is formed on the first electrode 360 ​​.

[0347] Reference Figure 5 The organic light emitting layer 362 includes a first light emitting portion 410 including a first EML 416 and a first ETL 420 , a second light emitting portion 430 including a second EML 434 and a second ETL 440 , and a charge generation layer (CGL) 450 between the first light emitting portion 410 and the second light emitting portion 430 .

[0348] The CGL 450 is located between the first light emitting portion 410 and the second light emitting portion 430, and the first light emitting portion 410, the CGL 450 and the second light emitting portion 430 are sequentially stacked on the first electrode 360. That is, the first light emitting portion 410 is located between the first electrode 360 ​​and the CGL 450, and the second light emitting portion 420 is located between the second electrode 364 and the CGL 450.

[0349] The first light emitting portion 410 may further include a first HTL 414 between the first electrode 360 ​​and the first EML 416. In addition, the first light emitting portion 410 may further include a HIL 412 between the first electrode 360 ​​and the first HTL 414.

[0350] Although not shown, the first light emitting portion 410 may further include at least one of an EBL between the first HTL 414 and the first EML 416 and an HBL between the first EML 416 and the first ETL 420 .

[0351] The second light emitting portion 430 may further include a second HTL 432 between the second EML 434 and the CGL 450. In addition, the second light emitting portion 430 may further include an EIL 436 between the second ETL 440 and the second electrode 364.

[0352] Although not shown, the second light emitting portion 430 may further include at least one of an EBL between the second HTL 432 and the second EML 434 and an HBL between the second EML 434 and the second ETL 440 .

[0353] One of the first EML 416 and the second EML 434 provides blue light emission, and the other of the first EML 416 and the second EML 434 provides yellow-green light emission. For example, the first EML 416 that can provide blue light emission may include a host and a blue dopant, and the second EML 434 that can provide yellow-green light emission may include a host and a yellow-green dopant. Alternatively, the second EML 434 may have a double-layer structure including a first layer that provides red light emission and a second layer that provides green light emission. In this case, the first layer that can provide red light emission may include a host and a red dopant, and the second layer that can provide green light emission may include a host and a green dopant.

[0354] For example, in the first EML 416 providing blue light emission, the host may be an anthracene derivative and the blue dopant may be a boron derivative.

[0355] The CGL 450 includes an n-type CGL 452 and a p-type CGL 454. The n-type CGL 452 is located between the first ETL 418 and the second HTL 432, and the p-type CGL 454 is located between the n-type CGL 452 and the second HTL 432.

[0356] The n-type CGL 452 supplies electrons to the first ETL 418, and the electrons are transferred to the first EML 416 through the first ETL 418. The p-type CGL 454 supplies holes to the second HTL 432, and the holes are transferred to the second EML 434 through the second HTL 432. Therefore, in the OLED D having a double stack (double layer) structure, the driving voltage is reduced, and the light emission efficiency is improved.

[0357] The p-type CGL 454 may be formed of an organic material doped with a metal or a p-type dopant. For example, the metal doped in the p-type CGL 454 may be selected from the group consisting of Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti, and the p-type dopant may be F4-TCNQ. The organic material in the p-type CGL 454 may be selected from NPB, TPD, N,N,N',N'-tetranaphthylbenzidine (TNB), and HAT-CN.

[0358] Alternatively, the p-type CGL 454 may include a compound represented by Formula 8-1 or 8-2.

[0359] [Formula 8-1]

[0360]

[0361] [Formula 8-2]

[0362]

[0363] In formulas 8-1 and 8-2, R1 to R6 are each independently selected from hydrogen, C6-C30 aryl, C6-C30 heteroaryl, C1-C12 alkyl, C1-C12 alkoxy, C2-C12 ether, cyano, fluorine, trifluoromethyl, trifluoromethoxy and trimethylsilyl, and at least one of R1 to R6 is cyano.

[0364] Z1 and Z2 are each independently represented by Formula 9.

[0365] [Formula 9]

[0366]

[0367] In Formula 9, A and B are each independently selected from hydrogen, C6-C30 aryl, C6-C30 heteroaryl, C1-C12 alkyl, C1-C12 alkoxy, C2-C12 ether, cyano, fluorine, trifluoromethyl, trifluoromethoxy and trimethylsilyl.

[0368] Each of the aryl group, heteroaryl group, alkyl group, alkoxy group and ether group may be unsubstituted or substituted with at least one of a C6-C30 aryl group, a C6-C30 heteroaryl group, a C1-C12 alkyl group, a cyano group, a fluorine group, a trifluoromethyl group, a trifluoromethoxy group and a trimethylsilyl group.

[0369] The compound in the p-type CGL 454 represented by Formula 8-1 or 8-2 may be one of the compounds in Formula 10.

[0370] [Formula 10]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378] At least one of the first ETL 420, the n-type CGL 452, and the second ETL 440 includes the organic compound of Formula 1-1. For example, the first ETL 420 includes the organic compound of the present invention as the first electron transport material 422. The second ETL 440 includes the organic compound of the present invention as the second electron transport material 442. The n-type CGL 452 includes the organic compound of the present invention as the n-type charge generation material 456.

[0379] The first electron transport material 422 of the first ETL 420 , the second electron transport material 442 of the second ETL 440 , and the n-type charge generation material 456 of the n-type CGL 452 may be the same or different.

[0380] When the n-type CGL 452 includes the organic compound of the present invention as the n-type charge generation material 456, the n-type CGL 452 may further include an auxiliary n-type charge generation material (not shown). 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. In the n-type CGL 452, the auxiliary n-type charge generation material may have a weight % of about 0.1 to 10 wt %, preferably about 0.5 to 5 wt %.

[0381] The OLED D including the first light emitting part 410 providing blue light emission and the second light emitting part 430 providing yellow-green light emission provides white light emission, and the CGL 450 including the organic compound of the present invention is disposed between the first light emitting part 410 and the second light emitting part 430. Therefore, the OLED D has advantages in driving voltage, light emission efficiency, and lifespan.

[0382] Reference Figure 6 The organic light emitting layer 362 includes a first light emitting portion 510 including a first EML 516 and a first ETL 520, a second light emitting portion 530 including a second EML 534 and a second ETL 540, a third light emitting portion 550 including a third EML 554 and a third ETL 560, a first CGL 570 located between the first light emitting portion 510 and the second light emitting portion 530, and a second CGL 580 between the second light emitting portion 530 and the third light emitting portion 550.

[0383] The first CGL 570 is located between the first light emitting portion 510 and the second light emitting portion 530, and the second CGL 580 is located between the second light emitting portion 530 and the third light emitting portion 550. That is, the first light emitting portion 510, the first CGL 570, the second light emitting portion 530, the second CGL 580 and the third light emitting portion 550 are sequentially stacked on the first electrode 360. In other words, the first light emitting portion 510 is located between the first electrode 360 ​​and the first CGL 570, the second light emitting portion 530 is located between the first CGL 570 and the second CGL 580, and the third light emitting portion 550 is located between the second electrode 360 ​​and the second CGL 580.

[0384] The first light emitting portion 510 may further include a first HTL 514 between the first electrode 360 ​​and the first EML 516. In addition, the first light emitting portion 510 may further include a HIL 512 between the first electrode 360 ​​and the first HTL 514.

[0385] Although not shown, the first light emitting portion 510 may further include at least one of an EBL between the first HTL 514 and the first EML 516 and an HBL between the first EML 516 and the first ETL 520 .

[0386] The second light emitting portion 530 may further include a second HTL 532 under the second EML 534 .

[0387] Although not shown, the second light emitting portion 510 may further include at least one of an EBL between the second HTL 532 and the second EML 534 and an HBL between the second EML 534 and the second ETL 550 .

[0388] The third light emitting portion 550 may further include a third HTL 552 between the third EML 554 and the second CGL 580. In addition, the third light emitting portion 550 may further include an EIL 556 between the third ETL 560 and the second electrode 364.

[0389] Although not shown, the third light emitting portion 550 may further include at least one of an EBL between the third HTL 552 and the third EML 554 and an HBL between the third EML 554 and the third ETL 560 .

[0390] Each of the first EML 516 and the third EML 554 provides blue light emission, and the third EML 534 provides yellow-green light emission. For example, the first EML 516 and the third EML 554 that can provide blue light emission may include a host and a blue dopant, and the second EML 534 that can provide yellow-green light emission may include a host and a yellow-green dopant. Alternatively, the second EML 534 may have a double-layer structure including a first layer that provides red light emission and a second layer that provides green light emission. In addition, the second EML 534 may have a three-layer structure including a first layer that provides red light emission and includes a host and a red dopant, a second layer that provides yellow-green light emission and includes a host and a yellow-green dopant, and a third layer that provides green light emission and includes a host and a green dopant.

[0391] For example, in the first EML 516 and the third EML 554 each providing blue light emission, a host may be an anthracene derivative and a blue dopant may be a boron derivative.

[0392] 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 520 and the second HTL 532, and the first p-type CGL 574 is located between the first n-type CGL 572 and the second HTL 532.

[0393] The second CGL 580 includes the second n-type CGL 582 and the second p-type CGL 584. The second n-type CGL 582 is located between the second ETL 540 and the third HTL 552, and the second p-type CGL 584 is located between the second n-type CGL 582 and the third HTL 552.

[0394] The first n-type CGL 572 supplies electrons to the first ETL 520, and the electrons are transferred to the first EML 516 through the first ETL 520. The first p-type CGL 574 supplies holes to the second HTL 532, and the holes are transferred to the second EML 534 through the second HTL 532.

[0395] The second n-type CGL 582 supplies electrons to the second ETL 540, and the electrons are transferred to the second EML 534 through the second ETL 540. The second p-type CGL 584 supplies holes to the third HTL 552, and the holes are transferred to the third EML 554 through the third HTL 552.

[0396] As a result, in the OLED D having a three-layer (tri-layer) structure, the driving voltage is reduced and the light emission efficiency is improved.

[0397] For example, each of the first and second p-type CGLs 574 and 584 may include one of HAT-CN and a compound represented by Formula 8-1 or 8-2. In addition, each of the first and second p-type CGLs 574 and 584 may further include a metal or a p-type dopant.

[0398] At least one of the first ETL 520, the first n-type CGL 572, the second ETL 540, the second n-type CGL 582, and the third ETL 560 includes the organic compound of Formula 1-1. For example, the first ETL 520 may include the organic compound of the present invention as the first electron transport material 522. The second ETL 540 may include the organic compound of the present invention as the second electron transport material 542. The third ETL 560 may include the organic compound of the present invention as the third electron transport material 562. The first n-type CGL 572 may include the organic compound of the present invention as the first n-type charge generation material 576. The second n-type CGL 582 may include the organic compound of the present invention as the second n-type charge generation material 586.

[0399] The first electron transport material 522 of the first ETL 520 , the second electron transport material 542 of the second ETL 540 , the third electron transport material 562 of the third ETL 560 , the first n-type charge generation material 576 of the first n-type CGL 574 , and the second n-type charge generation material 586 of the second n-type CGL 582 may be the same or different.

[0400] When each of the first n-type CGL 572 and the second n-type CGL 582 includes the organic compound of the present invention as the first n-type CGL 572 and the second n-type charge generating material, respectively, the first n-type CGL 572 and the second n-type CGL 582 may further include an auxiliary n-type charge generating material (not shown). For example, the auxiliary n-type charge generating 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. In each of the first n-type CGL 572 and the second n-type CGL 582, the auxiliary n-type charge generating material may have a weight % of about 0.1 to 10 wt %, preferably about 0.5 to 5 wt %.

[0401] The OLED D providing white light emission includes the first light emitting portion 510 and the third light emitting portion 550 each providing blue light emission and the second light emitting portion 530 providing yellow-green light emission, and the first CGL 570 and the second CGL 580 including the organic compound of the present invention are respectively disposed between the first light emitting portion 510 and the second light emitting portion 530 and between the second light emitting portion 530 and the third light emitting portion 550. Therefore, the OLED D has advantages in driving voltage, light emission efficiency, and lifespan.

[0402] Refer again Figure 4 , a second electrode 364 is formed above the substrate 310 on which the organic light-emitting layer 362 is formed.

[0403] In the organic light emitting display device 300 , since light emitted from the organic light emitting 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.

[0404] The first electrode 360 ​​, the organic light emitting layer 362 and the second electrode 364 constitute an OLED D.

[0405] The color filter layer 380 is located above the OLED D and includes a red color filter 382, ​​a green color filter 384, and a blue color filter 386 corresponding to the red, green, and blue pixel regions RP, GP, and BP, respectively. The red color filter 382 may include at least one of a red dye and a red pigment, the green color filter 384 may include at least one of a green dye and a green pigment, and the blue color filter 386 may include at least one of a blue dye and a blue pigment.

[0406] Although not shown, the color filter layer 380 may be attached to the OLED D through an adhesive layer. Alternatively, the color filter layer 380 may be formed directly on the OLED D.

[0407] 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 sequentially stacked, but is not limited thereto. The encapsulation film may be omitted.

[0408] 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.

[0409] exist Figure 4 In the OLED, 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 disposed 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 disposed between the OLED D and the first substrate 310 .

[0410] 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 pixel regions RP, GP, and BP, respectively. White light emitted by the OLED D is converted into red light, green light, and blue light by the red, green, and blue color conversion layers, respectively. For example, the color conversion layer may include quantum dots. Therefore, the color purity of the organic light emitting display device 300 may be further improved.

[0411] A color conversion layer may be used instead of the color filter layer 380 .

[0412] As described above, in the organic light emitting display device 300, the OLED D emits white light in the red, green, and blue pixel regions RP, GP, and BP, and the white light from the organic light emitting diode D passes through the red color filter 382, ​​the green color filter 384, and the blue color filter 386. As a result, red light, green light, and blue light are provided from the red pixel region RP, the green pixel region GP, ​​and the blue pixel region BP, respectively.

[0413] exist Figure 4 In the embodiment, the OLED D emitting white light is used for a display device. Alternatively, the OLED D may be formed on the entire surface of the substrate without at least one of a driving element and a color filter layer for a light emitting device. A display device and a light emitting device including the OLED D of the present invention, respectively, may be referred to as an organic light emitting device.

[0414] In the OLED D and the organic light emitting display device 300, at least one of the ETL and the n-type CGL includes the organic compound of the present invention, thereby improving the electron transport characteristics into the EML. Therefore, in the OLED and the display device 300, the driving voltage is reduced, and the light emitting efficiency and lifespan are improved.

[0415] Although the present disclosure has been described with reference to exemplary embodiments and examples, these embodiments and examples are not intended to limit the scope of the present invention. On the contrary, it will be apparent to those skilled in the art that various modifications and variations may be made to the present invention without departing from the spirit or scope of the present invention. Therefore, the present invention is intended to cover modifications and variations of the present disclosure as long as they fall within the scope of the appended claims and their equivalents.

[0416] The various embodiments described above may be combined to provide further embodiments. All patents, patent application publications, patent applications, foreign patents, foreign patent applications, and non-patent publications mentioned in this specification and / or listed in the application data sheet are incorporated herein by reference in their entirety. If necessary, aspects of the embodiments may be modified to adopt the concepts of the various patents, applications, and publications to provide further embodiments.

[0417] These and other changes can be made to the embodiments in light of the above detailed description. In general, in the following claims, the terms used should not be interpreted to limit the claims to the specific embodiments disclosed in the specification and claims, but should be interpreted to include all possible embodiments and the full scope of equivalents to these claims. Therefore, the claims are not limited by the invention.

Claims

1. An organic compound, which is one of the compounds in Formula 2: [Formula 2] 2. An organic light emitting diode, comprising: a first electrode; a second electrode facing the first electrode; as well as a first light emitting portion including a first light emitting material layer and a first electron transport layer and located between the first electrode and the second electrode, The first electron transport layer includes a first electron transport material and is located between the first light emitting material layer and the second electrode, Wherein the first electron transport material is an organic compound, and the organic compound is one of the compounds in Formula 2: [Formula 2] 3. The organic light emitting diode according to claim 2, further comprising: a second light-emitting portion including a second light-emitting material layer and a second electron transport layer and located between the first light-emitting portion and a second electrode, the second electron transport layer including a second electron transport material and located between the second light-emitting material layer and the second electrode; and A first n-type charge generation layer includes a first n-type charge generation material and is located between the first light emitting portion and the second light emitting portion. 4 . The organic light emitting diode according to claim 3 , wherein at least one of the second electron transport material and the first n-type charge generation material is an organic compound represented by Formula 2. 5 . The organic light emitting diode according to claim 3 , wherein the first light emitting material layer emits blue light, and the second light emitting material layer emits yellow-green light. 6 . The organic light emitting diode according to claim 3 , wherein the first light emitting material layer emits blue light, and the second light emitting material layer comprises a first layer emitting red light and a second layer emitting green light.

7. The organic light emitting diode according to claim 3, further comprising: a third light-emitting portion including a third light-emitting material layer and a third electron transport layer and located between the second light-emitting portion and the second electrode, the third electron transport layer including a third electron transport material and located between the third light-emitting material layer and the second electrode; and A second n-type charge generation layer includes a second n-type charge generation material and is located between the second light emitting portion and the third light emitting portion. 8 . The organic light emitting diode according to claim 7 , wherein at least one of the second electron transport material, the third electron transport material, the first n-type charge generation material, and the second n-type charge generation material is an organic compound represented by Formula 2. 9 . The organic light emitting diode according to claim 7 , wherein the first light emitting material layer and the second light emitting material layer each emit blue light, and the second light emitting material layer emits yellow-green light. 10 . The organic light emitting diode according to claim 7 , wherein the first light emitting material layer and the third light emitting material layer each emit blue light, and the second light emitting material layer includes a first layer emitting red light and a second layer emitting green light.

11. An organic light emitting diode, comprising: a first electrode; a second electrode facing the first electrode; a first light emitting portion including a first light emitting material layer and located between the first electrode and the second electrode; a second light-emitting portion including a second light-emitting material layer and a second electron transport layer and located between the first light-emitting portion and the second electrode; as well as a first n-type charge generation layer including a first n-type charge generation material and located between the first light emitting portion and the second light emitting portion, Wherein the first n-type charge generating material is an organic compound, and the organic compound is one of the compounds in Formula 2: [Formula 2] 12 . The organic light emitting diode according to claim 11 , wherein the first n-type charge generation layer further comprises a metal or a p-type dopant.

13. The organic light emitting diode according to claim 11, further comprising: a third light emitting portion including a third light emitting material layer and located between the second light emitting portion and the second electrode; and A second n-type charge generation layer includes a second n-type charge generation material and is located between the second light emitting portion and the third light emitting portion. 14 . The organic light emitting diode according to claim 13 , wherein the second n-type charge generating material is an organic compound represented by Formula 2.

15. An organic light-emitting device, comprising: substrate; an organic light emitting diode according to any one of claims 2 to 14 over the substrate; as well as A packaging film covers the organic light emitting diode.

16. The organic light-emitting device according to claim 15, wherein a red pixel region, a green pixel region, and a blue pixel region are defined on the substrate, and the organic light-emitting diode is connected to each of the red pixel region, the green pixel region, and the blue pixel region, and The organic light-emitting device further comprises: A color filter layer is disposed between the substrate and the organic light emitting diode or on the organic light emitting diode and corresponds to the red pixel region, the green pixel region, and the blue pixel region.

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