Light-emitting compound and organic light-emitting device containing the same

Abstract

The present disclosure relates to a light-emitting compound and an organic light-emitting device comprising the same, and more particularly, to the following light-emitting compound, and an organic light-emitting diode and an organic light-emitting device each comprising the light-emitting compound. #imgabs0#

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of Korean Patent Application No. 10-2020-0186024 filed in the Republic of Korea on December 29, 2020 and Korean Patent Application No. 10-2021-0135747 filed in the Republic of Korea on October 13, 2021, which are all incorporated herein by reference in their entirety. Technical Field

[0003] The present disclosure relates to a light-emitting compound, and more particularly, to a light-emitting compound having high light-emitting efficiency and lifetime and an organic light-emitting device including the same. Background Art

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

[0005] OLED injects electrons from the cathode as an electron injection electrode and holes from the anode as a hole injection electrode into the emitting material layer (EML), so that the electrons and holes are combined, excitons are generated, and the excitons are converted from the excited state to the ground state to emit light. A flexible substrate such as a plastic substrate can be used as a base substrate in which elements are formed. In addition, the organic light-emitting display device can operate at a lower voltage (e.g., 10V or lower) than the voltage required to operate other display devices. In addition, the organic light-emitting display device has advantages in power consumption and color perception.

[0006] For example, the organic light emitting display device may include a red pixel region, a green pixel region, and a blue pixel region, and an OLED may be formed in each of the red pixel region, the green pixel region, and the blue pixel region.

[0007] However, the OLED in the blue pixel cannot provide sufficient luminous efficiency and lifespan, so that the organic light emitting display device has limitations in terms of luminous efficiency and lifespan. Summary of the invention

[0008] The present disclosure relates to a light-emitting compound and an organic light-emitting device including the same that substantially obviates one or more of the problems associated with limitations and disadvantages of the related conventional technology.

[0009] Additional features and advantages of the present disclosure are set forth in the following description and will become apparent from the description or will become apparent 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.

[0010] To achieve these and other advantages according to the purpose of the embodiments of the present disclosure, as described herein, one aspect of the present disclosure is a light-emitting compound represented by Formula 1: [Formula 1] wherein n is 0 or 1, and X is one of B, P=O and P=S, wherein Y1 and Y2 are each independently selected from NR1, C(R2)2, O, S, Se and Si(R3)2, and Y3 is O or S, wherein R1 to R3 are each independently selected from hydrogen, deuterium (D), C1 to C10 alkyl unsubstituted or substituted with deuterium, C6 to C30 aromatic alkyl unsubstituted or substituted with deuterium or C1 to C10 alkyl, C6 to C30 aryl unsubstituted or substituted with deuterium or C1 to C10 alkyl, and C5 to C30 heteroaryl unsubstituted or substituted with deuterium or C1 to C10 alkyl, wherein R4 to R7 are each independently selected from hydrogen, deuterium, C1 to C10 alkyl unsubstituted or substituted with deuterium, C6 to C30 arylamine unsubstituted or substituted with deuterium or C1 to C10 alkyl, and C5 to C30 heteroaryl unsubstituted or substituted with deuterium or C1 to C10 alkyl. R4 to R7 are connected (combined) to form a ring, wherein R8 and R9 are each independently selected from hydrogen, deuterium, C1 to C10 alkyl unsubstituted or substituted with deuterium, C6 to C30 arylamine unsubstituted or substituted with deuterium or C1 to C10 alkyl, C6 to C30 aryl unsubstituted or substituted with deuterium or C1 to C10 alkyl, and C5 to C30 heteroaryl unsubstituted or substituted with deuterium or C1 to C10 alkyl, or R8 and R9 are connected to form a ring, and wherein the A ring and the E ring are each independently selected from a substituted or unsubstituted six-membered cycloalkyl ring, a substituted or unsubstituted six-membered aromatic ring, and a substituted or unsubstituted heteroaromatic condensed ring.

[0011] Another aspect of the present disclosure is an organic light-emitting device, which includes a substrate and an organic light-emitting diode, wherein the organic light-emitting diode is positioned on the substrate and includes: a first electrode; a second electrode facing the first electrode; and a first light-emitting material layer containing a first compound and positioned between the first electrode and the second electrode, wherein the first compound is the above light-emitting compound.

[0012] 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

[0013] The accompanying drawings, which are included to provide a further understanding of the disclosure and are incorporated in and constitute a part of this specification, illustrate embodiments of the disclosure and together with the description serve to explain the principles of the disclosure.

[0014] Figure 1 is a schematic circuit diagram showing an organic light emitting display device of the present disclosure.

[0015] Figure 2 is a schematic cross-sectional view showing an organic light emitting display device according to a first embodiment of the present disclosure.

[0016] Figure 3 is a schematic cross-sectional view showing an OLED having a single light emitting portion used for an organic light emitting display device according to a first embodiment of the present disclosure.

[0017] Figure 4 is a schematic cross-sectional view showing an OLED having a tandem structure of two light emitting parts for an organic light emitting display device according to a first embodiment of the present disclosure.

[0018] Figure 5 is a schematic cross-sectional view showing an organic light emitting display device according to a second embodiment of the present disclosure.

[0019] Figure 6 is a schematic cross-sectional view showing an OLED having a tandem structure of two light emitting parts for an organic light emitting display device according to a second embodiment of the present disclosure.

[0020] Figure 7 is a schematic cross-sectional view showing an OLED having a tandem structure of three light emitting parts for an organic light emitting display device according to a second embodiment of the present disclosure.

[0021] Figure 8 is a schematic cross-sectional view showing an organic light emitting display device according to a third embodiment of the present disclosure. DETAILED DESCRIPTION

[0022] Reference will now be made in detail to some examples and preferred embodiments which are illustrated in the accompanying drawings.

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

[0024] like Figure 1 As shown in FIG, in the organic light emitting display device, gate lines GL and data lines DL, and power lines PL are formed which cross each other to define pixels (pixel regions) P. A switching thin film transistor (TFT) Ts, a driving thin film transistor (TFT) Td, a storage capacitor Cst, and an OLED D are formed in the pixel region P. The pixel region P may include a red pixel, a green pixel, and a blue pixel.

[0025] The switching thin film transistor Ts is connected to the gate line GL and the data line DL, and the driving thin film transistor Td and the storage capacitor Cst are connected between the switching thin film transistor Ts and the power line PL. The OLED D is connected to the driving thin film transistor Td. When the switching thin film transistor Ts is turned on by a gate signal applied via the gate line GL, a data signal applied via the data line DL is applied to a gate electrode of the driving thin film transistor Td and one electrode of the storage capacitor Cst via the switching thin film transistor Ts.

[0026] The driving thin film transistor Td is turned on by the data signal applied to the gate electrode, so that a current proportional to the data signal is supplied from the power line PL to the OLED D via the driving thin film transistor Td. The OLED D emits light with a brightness proportional to the current flowing through the driving thin film transistor Td. In this case, the storage capacitor Cst is charged with a voltage proportional to the data signal, so that the voltage of the gate electrode in the driving thin film transistor Td is kept constant during one frame. Therefore, the organic light emitting display device can display a desired image.

[0027] Figure 2 is a schematic cross-sectional view showing an organic light emitting display device according to a first embodiment of the present disclosure.

[0028] like Figure 2 As shown in , the organic light emitting display device 100 includes a substrate 110, a TFT Tr, and an OLED D connected to the TFT Tr. For example, the organic light emitting display device 100 may include a red pixel, a green pixel, and a blue pixel, and an OLED D may be formed in each of the red pixel, the green pixel, and the blue pixel. That is, an OLED D emitting red light, green light, and blue light may be provided in the red pixel, the green pixel, and the blue pixel, respectively.

[0029] 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.

[0030] 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.

[0031] A semiconductor layer 122 is formed on the buffer layer 120. The semiconductor layer 122 may include an oxide semiconductor material or polysilicon.

[0032] 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, so that thermal degradation of the semiconductor layer 122 may be prevented. On the other hand, when the semiconductor layer 122 includes polycrystalline silicon, impurities may be doped into both sides of the semiconductor layer 122.

[0033] 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.

[0034] A gate electrode 130 made of a conductive material (eg, metal) is formed on the gate insulating layer 124 corresponding to the center of the semiconductor layer 122 .

[0035] 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.

[0036] 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.

[0037] 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 positioned at both sides of the gate electrode 130 to be spaced apart from the gate electrode 130.

[0038] 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 through only the interlayer insulating layer 132.

[0039] A source electrode 140 and a drain electrode 142 formed of a conductive material (eg, metal) are formed on the interlayer insulating layer 132 .

[0040] 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 contact hole 134 and the second contact hole 136 , respectively.

[0041] The semiconductor layer 122, the gate electrode 130, the source electrode 140, and the drain electrode 142 constitute a TFT Tr. The TFT Tr is used as a driving element. That is, the TFT Tr may correspond to ( Figure 1 ) driving TFT Td.

[0042] In the TFT Tr, the gate electrode 130, the source electrode 140, and the drain electrode 142 are positioned over the semiconductor layer 122. That is, the TFT Tr has a coplanar structure.

[0043] Alternatively, in the TFT Tr, the gate electrode may be positioned below the semiconductor layer, and the source electrode and the drain electrode may be positioned 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.

[0044] Although not shown, the gate lines and the data lines cross each other to define pixels, and a switching TFT is formed to be connected to the gate lines and the data lines. The switching TFT is connected to a TFT Tr as a driving element.

[0045] In addition, a power supply line may be formed to be parallel to and spaced apart from one of the gate line and the data line, and a storage capacitor for maintaining a voltage of a gate electrode of the TFT Tr in one frame may be further formed.

[0046] A passivation 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.

[0047] The first electrode 160 connected to the drain electrode 142 of the TFT Tr through the drain contact hole 152 is formed separately in each pixel and on the passivation layer 150. The first electrode 160 may be an anode and may be formed of a conductive material having a relatively high work function, such as a 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).

[0048] 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 under 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.

[0049] A bank layer 166 is formed on the passivation layer 150 to cover the edge of the first electrode 160. That is, the bank layer 166 is positioned at the boundary of the pixel and exposes the center of the first electrode 160 in the pixel.

[0050] An organic light emitting layer 162 is formed on the first electrode 160. The organic light emitting layer 162 may have a single-layer structure of a light emitting material layer including a light emitting material. In order to improve the light emitting efficiency of the OLED D and / or the organic light emitting display device 100, the organic light emitting layer 162 may have a multi-layer structure.

[0051] The organic light emitting layer 162 is separated in each of the red, green and blue pixels. As shown below, the organic light emitting layer 162 in the blue pixel includes the light emitting compound of Formula 1, so that the light emitting efficiency and life span of the OLED D in the blue pixel are improved.

[0052] A second electrode 164 is formed over the substrate 110 in 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), calcium (Ca), silver (Ag), or an alloy or combination thereof. In the top emission type organic light emitting display device 100, the second electrode 164 may have a thin profile (small thickness) to provide a light-transmitting property (or a semi-transparent property).

[0053] The first electrode 160 , the organic light emitting layer 162 , and the second electrode 164 constitute an OLED D.

[0054] 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 sequentially stacked, but is not limited thereto. The encapsulation film 170 may be omitted.

[0055] 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 top-emitting organic light-emitting display device 100, the polarizing plate may be arranged below the substrate 110. In a top-emitting organic light-emitting display device 100, the polarizing plate may be arranged on or above the encapsulation film 170.

[0056] 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.

[0057] Figure 3 is a schematic cross-sectional view showing an OLED having a single light emitting unit used for an organic light emitting display device according to a first embodiment of the present disclosure.

[0058] like Figure 3 As shown, the OLED D includes a first electrode 160 and a second electrode 164 facing each other and an organic light emitting layer 162 interposed therebetween. The organic light emitting layer 162 includes a light emitting material layer (EML) 240 between the first electrode 160 and the second electrode 164. Figure 2 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 positioned in the blue pixel.

[0059] One of the first electrode 160 and the second electrode 164 is an anode, and the other of the first electrode 160 and the second electrode 164 is a cathode. In addition, one of the first electrode 160 and the second electrode 164 may be a transparent (or semi-transparent) electrode, and the other of the first electrode 160 and the second electrode 164 may be a reflective electrode.

[0060] The organic light emitting layer 162 may further include an electron blocking layer (EBL) 230 between the first electrode 160 and the EML 240 , and a hole blocking layer (HBL) 250 between the EML 240 and the second electrode 164 .

[0061] In addition, the organic light emitting layer 162 may further include a hole transport layer (HTL) 220 between the first electrode 160 and the EBL 230 .

[0062] In addition, the organic light emitting layer 162 may further include a hole injection layer (HIL) 210 between the first electrode 160 and the HTL 220 and an electron injection layer (EIL) 260 between the second electrode 164 and the HBL 250 .

[0063] The EML 240 includes a light-emitting compound 242 as a first compound. The light-emitting compound is a polycyclic aromatic compound and is represented by Formula 1.

[0064] [Formula 1]

[0065]

[0066] In Formula 1, n is 0 or 1, and X is one of B, P═O and P═S. Y1 and Y2 are each independently selected from NR1, C(R2)2, O, S, Se and Si(R3)2, and Y3 is O or S. R1 to R3 are each independently selected from hydrogen, deuterium (D), C1 to C10 alkyl groups which are unsubstituted or substituted with deuterium, C6 to C30 arylamine groups which are unsubstituted or substituted with deuterium or C1 to C10 alkyl, C6 to C30 aryl groups which are unsubstituted or substituted with deuterium or C1 to C10 alkyl, and C5 to C30 heteroaryl groups which are unsubstituted or substituted with deuterium or C1 to C10 alkyl. In addition, R4 to R7 are each independently selected from hydrogen, deuterium, C1 to C10 alkyl groups which are unsubstituted or substituted with deuterium, C6 to C30 arylamine groups which are unsubstituted or substituted with deuterium or C1 to C10 alkyl groups, C6 to C30 aryl groups which are unsubstituted or substituted with deuterium or C1 to C10 alkyl groups, and C5 to C30 heteroaryl groups which are unsubstituted or substituted with deuterium or C1 to C10 alkyl groups, or two adjacent ones of R4 to R7 are connected (combined) to each other to form a ring. R8 and R9 are each independently selected from hydrogen, deuterium, C1 to C10 alkyl groups which are unsubstituted or substituted with deuterium, C6 to C30 arylamine groups which are unsubstituted or substituted with deuterium or C1 to C10 alkyl, C6 to C30 aryl groups which are unsubstituted or substituted with deuterium or C1 to C10 alkyl, and C5 to C30 heteroaryl groups which are unsubstituted or substituted with deuterium or C1 to C10 alkyl, or R8 and R9 are connected to each other to form a ring.

[0067] The A ring and the E ring are each independently selected from a substituted or unsubstituted six-membered cycloalkyl ring, a substituted or unsubstituted six-membered aromatic ring, and a substituted or unsubstituted heteroaromatic condensed ring.

[0068] The formed ring may be a C6 to C30 aromatic ring or a C5 to C30 heteroaromatic (condensed) ring. For example, the C6 to C30 aromatic ring may be a benzene ring or a naphthalene ring, and the condensed ring of the C5 to C30 heteroaromatic ring may be a thiophene ring, a furan ring, a benzothiophene ring or a benzofuran ring.

[0069] In each of the A ring and the E ring, hydrogen may be substituted with at least one of D, a C1 to C10 alkyl group, a C6 to C30 aryl group, and a C5 to C30 heteroaryl group.

[0070] For example, in Formula 1, n may be 0. That is, the five-membered ring including Y3 may be directly connected to X and Y2, and the light-emitting compound in Formula 1 may be represented by Formula 2-1.

[0071] [Formula 2-1]

[0072]

[0073] In addition, in Formula 2-1, X may be B, Y1 and Y2 may each be NR1, and the A ring and the E ring may each be an unsubstituted or substituted benzene ring. That is, the light-emitting compound in Formula 1 may be represented by Formula 2-2.

[0074] [Formula 2-2]

[0075]

[0076] In formula 2-2, R 21 To R 27 and are each independently selected from hydrogen, deuterium (D), C1-C10 alkyl unsubstituted or substituted with deuterium, C6-C30 arylamine unsubstituted or substituted with deuterium or C1-C10 alkyl, C6-C30 aryl unsubstituted or substituted with deuterium or C1-C10 alkyl, and C5-C30 heteroaryl unsubstituted or substituted with deuterium or C1-C10 alkyl.

[0077] For example, in Formula 2-2, R1 may be a C6 to C30 aryl group, such as a phenyl group. Two adjacent ones of R4 to R7 may be connected to each other to form a ring, and the other two of R4 to R7 may be hydrogen. 21 To R 27 It may be hydrogen.

[0078] Alternatively, in Formula 1, n may be 1. That is, the light-emitting compound in Formula 1 may be represented by Formula 3-1.

[0079] [Formula 3-1]

[0080]

[0081] In addition, in Formula 3-1, X may be B, Y1 and Y2 may each be NR1, and the A ring and the E ring may each be an unsubstituted or substituted benzene ring. That is, the light-emitting compound in Formula 1 may be represented by Formula 3-2.

[0082] [Formula 3-2]

[0083]

[0084] In formula 3-2, R 31 To R 37 and are each independently selected from hydrogen, deuterium (D), C1-C10 alkyl unsubstituted or substituted with deuterium, C6-C30 arylamine unsubstituted or substituted with deuterium or C1-C10 alkyl, C6-C30 aryl unsubstituted or substituted with deuterium or C1-C10 alkyl, and C5-C30 heteroaryl unsubstituted or substituted with deuterium or C1-C10 alkyl.

[0085] For example, in Formula 3-2, R1 may be a C6 to C30 aromatic group, such as a phenyl group. R8 and R9 or two adjacent ones of R4 to R7 may be connected to each other to form a C6 to C30 aromatic ring, such as a benzene ring, and the other two of R4 to R7 may be hydrogen. 31 To R 37 It may be hydrogen.

[0086] Alternatively, in Formula 3-1, the E ring may be a heteroaromatic condensed ring. That is, the light-emitting compound in Formula 1 may be represented by Formula 3-3.

[0087] [Formula 3-3]

[0088]

[0089] In Formula 3-3, Y4 is one of NR1, C(R2)2, O, S, Se and Si(R3)2. 10 To R 13 are each independently selected from hydrogen, deuterium, C1-C10 alkyl unsubstituted or substituted with deuterium, C6-C30 arylamine unsubstituted or substituted with deuterium or C1-C10 alkyl, C6-C30 aryl unsubstituted or substituted with deuterium or C1-C10 alkyl, and C5-C30 heteroaryl unsubstituted or substituted with deuterium or C1-C10 alkyl, or R 10 To R 13 Two adjacent ones of R are connected (combined) to each other to form a ring. 14 and R 15 are each independently selected from hydrogen, deuterium, C1-C10 alkyl unsubstituted or substituted with deuterium, C6-C30 arylamine unsubstituted or substituted with deuterium or C1-C10 alkyl, C6-C30 aryl unsubstituted or substituted with deuterium or C1-C10 alkyl, and C5-C30 heteroaryl unsubstituted or substituted with deuterium or C1-C10 alkyl, or R 14 and R 15 Connect (bind) to each other to form a ring.

[0090] The formed ring may be a C6 to C30 aromatic ring or a C5 to C30 heteroaromatic (condensed) ring.

[0091] In Formula 3-3, X may be B, Y1 and Y2 may each be NR1, and Ring A may be a benzene ring. That is, the light-emitting compound in Formula 1 may be represented by one of Formulas 3-4.

[0092] [Formula 3-4]

[0093]

[0094] In formula 3-4, R 41 To R43 and are each independently selected from hydrogen, deuterium, C1-C10 alkyl unsubstituted or substituted with deuterium, C6-C30 arylamine unsubstituted or substituted with deuterium or C1-C10 alkyl, C6-C30 aryl unsubstituted or substituted with deuterium or C1-C10 alkyl, and C5-C30 heteroaryl unsubstituted or substituted with deuterium or C1-C10 alkyl.

[0095] For example, in Formula 3-4, R1 may be a C6 to C30 aromatic group, such as a phenyl group. R8 and R9 or two adjacent ones of R4 to R7 may be connected to each other to form a C6 to C30 aromatic ring, such as a benzene ring, or R 14 and R 15 or R 10 To R 13 Two adjacent ones of R4 to R7 may be connected to each other to form a C6 to C30 aromatic ring, such as a benzene ring. The other two of R4 to R7, R 10 To R 13 The other two, and R 41 To R 43 It may be hydrogen.

[0096] The luminescent compound in Formula 1 of the present disclosure may be one of the compounds in Formula 4.

[0097] [Formula 4]

[0098]

[0099] The light-emitting compound in Formula 1 provides blue light emission and is used for the EML 240 in the OLED D. Therefore, the lifespan of the OLED D and the organic light-emitting display device 100 is significantly improved.

[0100] [Synthesis of dopant]

[0101] 1. Synthesis of Compound 1-1

[0102] (1) Compound I1-1c

[0103] [Reaction formula 1-1]

[0104]

[0105] In a 500 mL reactor, add compound I1-1a 8.5 g (50 mmol), compound I1-1b 20.2 g (50 mmol), palladium acetate 0.45 g (2 mmol), sodium tert-butoxide 18.9 g (196 mmol), tri-tert-butylphosphine 0.8 g (4 mmol) and 300 mL toluene, and stir / reflux for 5 hours. After the reaction is completed, the resultant is filtered and concentrated. The mixture is separated by column chromatography to obtain 16.1 g of compound I1-1c. (Yield 60%)

[0106] (2) Compound 1-1

[0107] [Reaction 1-2]

[0108]

[0109] In a 500mL reactor, compound I1-1c 6.7g (12.5mmol) and tert-butylbenzene 60mL were added. 45mL (37.5mmol) of n-butyllithium was added dropwise at -78°C. After the addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown at 60°C to remove heptane. Boron tribromide 6.3g (25mmol) was added dropwise at -78°C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2g (25mmol) of N,N-diisopropylethylamine was added dropwise at 0°C. After the addition, the mixture was stirred at 120°C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.2g of compound 1-1. (yield 19%)

[0110] 2. Synthesis of Compound 1-2

[0111] (1) Compound I1-2c

[0112] [Reaction formula 2-1]

[0113]

[0114] In a 500 mL reactor, add compound I1-2a 8.5 g (50 mmol), compound I1-2b 20.2 g (50 mmol), palladium acetate 0.45 g (2 mmol), sodium tert-butoxide 18.9 g (196 mmol), tri-tert-butylphosphine 0.8 g (4 mmol) and 300 mL toluene, and stir / reflux for 5 hours. After the reaction is completed, the resultant is filtered and concentrated. The mixture is separated by column chromatography to obtain 16.1 g of compound I1-2c. (Yield 60%)

[0115] (2) Compound 1-2

[0116] [Reaction formula 2-2]

[0117]

[0118] In a 500mL reactor, compound I1-2c 6.7g (12.5mmol) and tert-butylbenzene 60mL were added to a 500mL reactor. 45mL (37.5mmol) of n-butyllithium was added dropwise at -78°C. After the addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown at 60°C to remove heptane. Boron tribromide 6.3g (25mmol) was added dropwise at -78°C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2g (25mmol) of N,N-diisopropylethylamine was added dropwise at 0°C. After the addition, the mixture was stirred at 120°C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.1g of compound 1-2. (yield 18%)

[0119] 3. Synthesis of Compounds 1-3

[0120] (1) Compound I1-3c

[0121] [Reaction formula 3-1]

[0122]

[0123] In a 500 mL reactor, add compound I1-3a 8.5 g (50 mmol), compound I1-3b 20.2 g (50 mmol), palladium acetate 0.45 g (2 mmol), sodium tert-butoxide 18.9 g (196 mmol), tri-tert-butylphosphine 0.8 g (4 mmol) and 300 mL toluene, and stir / reflux for 5 hours. After the reaction is completed, the resultant is filtered and concentrated. The mixture is separated by column chromatography to obtain 17.2. g of compound I1-3c. (Yield 64%)

[0124] (2) Compound 1-3

[0125] [Reaction formula 3-2]

[0126]

[0127] In a 500mL reactor, compound I1-3c 6.7g (12.5mmol) and tert-butylbenzene 60mL were added. 45mL (37.5mmol) of n-butyllithium was added dropwise at -78°C. After the addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown at 60°C to remove heptane. Boron tribromide 6.3g (25mmol) was added dropwise at -78°C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2g (25mmol) of N,N-diisopropylethylamine was added dropwise at 0°C. After the addition, the mixture was stirred at 120°C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.2g of compound 1-3. (yield 19%)

[0128] 4. Synthesis of Compounds 1-4

[0129] (1) Compound I1-4c

[0130] [Reaction 4-1]

[0131]

[0132] In a 500 mL reactor, add compound I1-4a 8.5 g (50 mmol), compound I1-4b 21.0 g (50 mmol), palladium acetate 0.45 g (2 mmol), sodium tert-butoxide 18.9 g (196 mmol), tri-tert-butylphosphine 0.8 g (4 mmol) and 300 mL toluene, and stir / reflux for 5 hours. After the reaction is completed, the resultant is filtered and concentrated. The mixture is separated by column chromatography to obtain 17.1 g of compound I1-4c. (Yield 62%)

[0133] (2) Compound 1-4

[0134] [Reaction 4-2]

[0135]

[0136] In a 500mL reactor, compound I1-4c 6.9g (12.5mmol) and tert-butylbenzene 60mL were added. 45mL (37.5mmol) of n-butyllithium was added dropwise at -78°C. After the addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown at 60°C to remove heptane. Boron tribromide 6.3g (25mmol) was added dropwise at -78°C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2g (25mmol) of N,N-diisopropylethylamine was added dropwise at 0°C. After the addition, the mixture was stirred at 120°C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.3g of compound 1-4. (yield 19%)

[0137] 5. Synthesis of Compounds 1-6

[0138] (1) Compound I1-6c

[0139] [Reaction formula 5-1]

[0140]

[0141] In a 500 mL reactor, add compound I1-6a 8.5 g (50 mmol), compound I1-6b 21.0 g (50 mmol), palladium acetate 0.45 g (2 mmol), sodium tert-butoxide 18.9 g (196 mmol), tri-tert-butylphosphine 0.8 g (4 mmol) and 300 mL toluene, and stir / reflux for 5 hours. After the reaction is completed, the resultant is filtered and concentrated. The mixture is separated by column chromatography to obtain 16.6 g of compound I1-6c. (yield 60%)

[0142] (2) Compound 1-6

[0143] [Reaction 5-2]

[0144]

[0145] In a 500mL reactor, compound I1-6c 6.9g (12.5mmol) and tert-butylbenzene 60mL were added. 45mL (37.5mmol) of n-butyllithium was added dropwise at -78°C. After the addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown at 60°C to remove heptane. Boron tribromide 6.3g (25mmol) was added dropwise at -78°C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2g (25mmol) of N,N-diisopropylethylamine was added dropwise at 0°C. After the addition, the mixture was stirred at 120°C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.4g of compound 1-6. (yield 21%)

[0146] 6. Synthesis of Compound 2-1

[0147] (1) Compound I2-1c

[0148] [Reaction formula 6-1]

[0149]

[0150] In a 500 mL reactor, compound I2-1a 8.5 g (50 mmol), compound I2-1b 22.7 g (50 mmol), palladium acetate 0.45 g (2 mmol), sodium tert-butoxide 18.9 g (196 mmol), tri-tert-butylphosphine 0.8 g (4 mmol) and 300 mL toluene were added and stirred under reflux for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 18.2 g of compound I2-1c. (Yield 62%)

[0151] (2) Compound 2-1

[0152] [Reaction formula 6-2]

[0153]

[0154] In a 500mL reactor, compound I2-1c 7.3g (12.5mmol) and tert-butylbenzene 60mL were added. 45mL (37.5mmol) of n-butyllithium was added dropwise at -78°C. After the addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown at 60°C to remove heptane. Boron tribromide 6.3g (25mmol) was added dropwise at -78°C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2g (25mmol) of N,N-diisopropylethylamine was added dropwise at 0°C. After the addition, the mixture was stirred at 120°C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.4g of compound 2-1. (yield 20%)

[0155] 7. Synthesis of Compound 2-2

[0156] (1) Compound I2-2c

[0157] [Reaction formula 7-1]

[0158]

[0159] In a 500 mL reactor, compound I2-2a 8.5 g (50 mmol), compound I2-2b 22.7 g (50 mmol), palladium acetate 0.45 g (2 mmol), sodium tert-butoxide 18.9 g (196 mmol), tri-tert-butylphosphine 0.8 g (4 mmol) and 300 mL toluene were added and stirred under reflux for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 17.6 g of compound I2-2c. (Yield 60%)

[0160] (2) Compound 2-2

[0161] [Reaction 7-2]

[0162]

[0163] In a 500mL reactor, compound I2-2c 7.3g (12.5mmol) and tert-butylbenzene 60mL were added. 45mL (37.5mmol) of n-butyllithium was added dropwise at -78°C. After the addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown at 60°C to remove heptane. Boron tribromide 6.3g (25mmol) was added dropwise at -78°C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2g (25mmol) of N,N-diisopropylethylamine was added dropwise at 0°C. After the addition, the mixture was stirred at 120°C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.5g of compound 2-2. (yield 22%)

[0164] 8. Synthesis of Compound 2-3

[0165] (1) Compound I2-3c

[0166] [Reaction formula 8-1]

[0167]

[0168] In a 500 mL reactor, compound I2-3a 8.5 g (50 mmol), compound I2-3b 22.7 g (50 mmol), palladium acetate 0.45 g (2 mmol), sodium tert-butoxide 18.9 g (196 mmol), tri-tert-butylphosphine 0.8 g (4 mmol) and 300 mL toluene were added and stirred under reflux for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 19.1 g of compound I2-3c. (Yield 65%)

[0169] (2) Compound 2-3

[0170] [Reaction formula 8-2]

[0171]

[0172] In a 500mL reactor, compound I2-3c 7.3g (12.5mmol) and tert-butylbenzene 60mL were added. 45mL (37.5mmol) of n-butyllithium was added dropwise at -78°C. After the addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown at 60°C to remove heptane. Boron tribromide 6.3g (25mmol) was added dropwise at -78°C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2g (25mmol) of N,N-diisopropylethylamine was added dropwise at 0°C. After the addition, the mixture was stirred at 120°C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.6g of compound 2-3. (yield 20%)

[0173] 9. Synthesis of Compound 2-4

[0174] (1) Compound I2-4c

[0175] [Reaction formula 9-1]

[0176]

[0177] In a 500 mL reactor, compound I2-4a 8.5 g (50 mmol), compound I2-4b 22.7 g (50 mmol), palladium acetate 0.45 g (2 mmol), sodium tert-butoxide 18.9 g (196 mmol), tri-tert-butylphosphine 0.8 g (4 mmol) and 300 mL toluene were added and stirred under reflux for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 19.1 g of compound I2-4c. (Yield 65%)

[0178] (2) Compound 2-4

[0179] [Reaction formula 9-2]

[0180]

[0181] In a 500mL reactor, compound I2-4c 7.3g (12.5mmol) and tert-butylbenzene 60mL were added. 45mL (37.5mmol) of n-butyllithium was added dropwise at -78°C. After the addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown at 60°C to remove heptane. Boron tribromide 6.3g (25mmol) was added dropwise at -78°C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2g (25mmol) of N,N-diisopropylethylamine was added dropwise at 0°C, and after the addition, the mixture was stirred at 120°C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.5g of compound 2-4. (yield 21%)

[0182] 10. Synthesis of Compound 2-5

[0183] (1) Compound I2-5c

[0184] [Reaction formula 10-1]

[0185]

[0186] In a 500 mL reactor, compound I2-5a 34.0 g (110 mmol), compound I2-5b 9.1 g (50 mmol), palladium acetate 0.45 g (2 mmol), sodium tert-butoxide 18.9 g (196 mmol), tri-tert-butylphosphine 0.8 g (4 mmol) and 300 mL toluene were added and stirred under reflux for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 23.6 g of compound I2-5c. (Yield 65%)

[0187] (2) Compound 2-5

[0188] [Reaction formula 10-2]

[0189]

[0190] In a 500mL reactor, compound I2-5c 9.1g (12.5mmol) and tert-butylbenzene 60mL were added. 45mL (37.5mmol) of n-butyllithium was added dropwise at -78°C. After the addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown at 60°C to remove heptane. Boron tribromide 6.3g (25mmol) was added dropwise at -78°C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2g (25mmol) of N,N-diisopropylethylamine was added dropwise at 0°C. After the addition, the mixture was stirred at 120°C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.6g of compound 2-5. (yield 18%)

[0191] 11. Synthesis of Compound 2-8

[0192] (1) Compound I2-8c

[0193] [Reaction formula 11-1]

[0194]

[0195] In a 500 mL reactor, compound I2-8a 34.0 g (110 mmol), compound I2-8b 9.1 g (50 mmol), palladium acetate 0.45 g (2 mmol), sodium tert-butoxide 18.9 g (196 mmol), tri-tert-butylphosphine 0.8 g (4 mmol) and 300 mL toluene were added and stirred under reflux for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 22.1 g of compound I2-8c. (Yield 61%)

[0196] (2) Compound 2-8

[0197] [Reaction formula 11-2]

[0198]

[0199] In a 500mL reactor, compound I2-8c 9.1g (12.5mmol) and tert-butylbenzene 60mL were added. 45mL (37.5mmol) of n-butyllithium was added dropwise at -78°C. After the addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown at 60°C to remove heptane. Boron tribromide 6.3g (25mmol) was added dropwise at -78°C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2g (25mmol) of N,N-diisopropylethylamine was added dropwise at 0°C. After the addition, the mixture was stirred at 120°C for 2 hours. After the reaction was completed, sodium acetate aqueous solution was added thereto and stirred at room temperature. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.5g of compound 2-8. (yield 17%)

[0200] In the EML 240 , the first compound 242 acts as a dopant (luminescent body) to emit blue light.

[0201] In addition, the EML 240 may further include a second compound 244 as a main body. In this case, in the EML 240, the weight % of the first compound 242 may be about 0.1 weight % to 30 weight %, preferably about 0.1 weight % to 10 weight %, and more preferably about 1 weight % to 5 weight %. The thickness of the EML 240 may be about to Preferably about to and more preferably about to

[0202] The second compound 244 as a host may be an anthracene derivative. For example, the second compound 244 may be represented by Formula 5.

[0203] [Formula 5]

[0204]

[0205] In Formula 5, Ar1 and Ar2 are each independently an unsubstituted or substituted C6 to C30 aryl group or an unsubstituted or substituted C5 to C30 heteroaryl group. L is a single bond or an unsubstituted or substituted C6 to C60 arylene group. In this case, the hydrogen in the anthracene derivative is undeuterated or partially or fully deuterated. That is, no hydrogen, some hydrogen, or all hydrogen in the anthracene derivative is substituted with deuterium.

[0206] In Formula 5, Ar1 and Ar2 may each be selected from a phenyl group, a naphthyl group, a dibenzofuranyl group, and a condensed dibenzofuranyl group, and L may be a single bond or a phenylene group.

[0207] For example, Ar1 may be selected from naphthyl, dibenzofuranyl, phenyl-dibenzofuranyl and fused dibenzofuranyl, and Ar2 may be selected from phenyl and naphthyl. In one embodiment, Ar1 and Ar2 may be naphthyl, and L may be a single bond or a phenylene group.

[0208] In Formula 5, the anthracene nucleus may be partially or fully deuterated, or Ar1, Ar2, and L may each be partially or fully deuterated. Alternatively, the anthracene nucleus, Ar1, Ar2, and L may each be partially or fully deuterated.

[0209] The second compound 244 in Formula 5 may be one of the compounds in Formula 6. In compounds H5 to H8, "D" represents a deuterium atom, and "x" in "Dx" represents the number of deuterium atoms.

[0210] [Formula 6]

[0211]

[0212] The HIL 210 may include at least one compound selected from the group consisting of 4,4'4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4"-tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4',4"-tris(N-(naphthalen-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-tris(N-(naphthalen-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"-diamine (NPB or 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-(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-carbazole-3-yl)phenyl)-9H-fluoren-2-amine. Alternatively, the HIL 210 may include a compound of Formula 13 as a host and a compound of Formula 14 as a dopant.

[0213] The HTL 220 may include at least one compound selected from the group consisting of N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), NPB (or NPD), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)-benzidine] (poly-TPD), poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)-1,1'-biphenyl)-4,4'-diamine ...

[0063] In some embodiments, HTL 220 may include bis-[4-(N,N-di-p-tolyl-amino)-phenyl]cyclohexane (TAPC), 3,5-bis(9H-carbazole-9-yl)-N,N'-diphenylaniline (DCDPA), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, and N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)biphenyl-4-amine. Alternatively, HTL 220 may include a compound of Formula 13 below.

[0214] The EBL 230 disposed between the HTL 220 and the EML 240 is formed to prevent electrons from flowing toward the HTL 220. The EBL 230 includes an electron blocking material of an amine derivative.

[0215] [Formula 7]

[0216]

[0217] In Formula 7, L is a C6 to C30 arylene group, and a is 0 or 1. R1 and R2 are each independently selected from an unsubstituted or substituted C6 to C30 aryl group and an unsubstituted or substituted C5 to C30 heteroaryl group.

[0218] For example, L may be a phenylene group, and R1 and R2 may each be selected from a biphenyl group, a dimethyl-substituted fluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a carbazolylphenyl group, a dibenzothienyl group, and a dibenzofuranyl group.

[0219] That is, the electron blocking material may be a spirofluorene-substituted amine derivative (eg, a "spirofluorene-substituted amine derivative").

[0220] The electron blocking material of Formula 7 may be one of the following Formula 8:

[0221] [Formula 8]

[0222]

[0223]

[0224] The HBL 250 disposed between the EML 240 and the EIL 260 is formed to prevent holes from flowing toward the EIL 260. The HBL 250 includes a hole blocking material of an azine derivative. The azine derivative as the hole blocking material is represented by Formula 9.

[0225] [Formula 9]

[0226]

[0227] In Formula 9, Y1 to Y5 are each independently CR1 or N, and one to three of Y1 to Y5 are N. R1 is independently C6 to C30 aryl. L is C6 to C30 arylene, and R2 is C6 to C30 aryl or C5 to C30 heteroaryl, wherein C6 to C30 aryl is optionally substituted by another C6 to C30 aryl or C5 to C30 heteroaryl or forms a spiral structure with a C10 to C30 fused aromatic ring or a C10 to C30 fused heteroaromatic ring, wherein another C6 to C30 aryl is optionally further substituted by another C6 to C30 aryl or C5 to C30 heteroaryl or forms a spiral structure with a C10 to C30 fused aromatic ring. R3 is hydrogen, or two adjacent R3 form a fused ring. "a" is 0 or 1, "b" is 1 or 2, and "c" is an integer of 0 to 4.

[0228] The hole blocking material of Formula 9 may be one of the following Formula 10.

[0229] [Formula 10]

[0230]

[0231]

[0232] Alternatively, the HBL 250 may include a benzimidazole derivative as a hole blocking material. For example, the benzimidazole derivative as the hole blocking material is represented by Formula 11-1 or Formula 11-2.

[0233] [Formula 11-1]

[0234]

[0235] [Formula 11-2]

[0236]

[0237] In formula 11-1, Ar is C 10 To C 30 Arylene, R1 is C6 to C 30 Aryl or C5 to C 30 heteroaryl, and R2 is hydrogen, C1 to C 10 Alkyl or C6 to C 30Aryl.

[0238] In formula 11-2, Ar is C 10 To C 30 Arylene, R1 is C6 to C 30 Aryl or C5 to C 30 Heteroaryl, C6 to C 30 Aryl and C5 to C 30 The heteroaryl groups are each optionally C1 to C 10 alkyl, and R2 and R3 are each independently hydrogen, C1 to C 10 Alkyl or C6 to C 30 Aryl.

[0239] For example, Ar may be naphthylene or anthracene, R1 may be benzimidazole or phenyl, and R2 may be methyl, ethyl or phenyl.

[0240] The hole blocking material of Formula 11-1 or Formula 11-2 may be one of the following Formula 12.

[0241] [Formula 12]

[0242]

[0243] The HBL 250 may include at least one of the hole blocking material in Formula 9 and the hole blocking material in Formula 11-1 or Formula 11-2.

[0244] In this case, the thickness of the EML 240 may be greater than the thickness of each of the EBL 230 and the HBL 250 and may be less than the thickness of the HTL 220. For example, the thickness of the EML 240 may be about 100 Å. to The thickness of each of the EBL 230 and the HBL 250 may be about to The thickness of HTL 220 may be about to The EBL 230 and the HBL 250 may have the same thickness.

[0245] The HBL 250 may include the compound of Formula 9 and the compound of Formula 11-1 or Formula 11-2. For example, in the HBL 250, the compound of Formula 9 and the compound of Formula 11-1 or Formula 11-2 may have the same weight %.

[0246] In this case, the thickness of the EML 240 may be greater than the thickness of the EBL 230 and may be less than the thickness of the HBL 250. In addition, the thickness of the HBL 250 may be less than the thickness of the HTL 220. For example, the thickness of the EML 240 may be about 100 Å. to The thickness of the EBL can be about to The thickness of HBL 250 may be about to The thickness of HTL 220 may be about to

[0247] The hole blocking material in Formula 9 and / or Formula 11-1 (or Formula 11-2) has excellent hole blocking properties and excellent electron transport properties. Therefore, an electron transport layer may be present, and the HBL 250 may directly contact the EIL 260 or the second electrode 164 .

[0248] The EIL 260 may include at least one of an alkali metal such as Li, an alkali halide compound such as LiF, CsF, NaF, or BaF2, and an organic metal compound such as Liq, lithium benzoate, or sodium stearate, but is not limited thereto. Alternatively, the EIL 260 may include a compound of Formula 15 as a host and an alkali metal as a dopant.

[0249] In the OLED D, the EML 240 includes the light-emitting compound 242 of Formula 1, so that the lifespan of the OLED D and the organic light-emitting display device 100 is significantly improved.

[0250] [Organic Light Emitting Diode]

[0251] The anode (ITO, 0.5 mm), HIL (Formula 13 (97 wt%) and Formula 14 (3 wt%), )、HTL(Formula 13、 ), EBL (compound EBL-11 in formula 8, ), EML (compound H-1 in Formula 6 (host, 98 wt%) and dopant (2 wt%), ), HBL (compound E1 in formula 10, ), EIL (Formula 15 (98 wt%) and Li (2 wt%), ) and cathode (Al, ) are sequentially deposited. An encapsulation film is formed by using a UV-curable epoxy compound and a moisture absorbent to form an OLED.

[0252] [Formula 13]

[0253]

[0254] [Formula 14]

[0255]

[0256] [Formula 15]

[0257]

[0258] (1) Comparative Examples 1 and 2 (Ref1 and Ref2)

[0259] The compound “Ref-1” in Formula 16 and the compound “Ref-2” in Formula 17 are respectively used as dopants to form the EML.

[0260] (2) Examples 1 to 11 (Ex1 to Ex11)

[0261] Compounds 1-1 to 1-4, 1-6, 2-1 to 2-5, and 2-8 in Formula 4 are respectively used as dopants to form the EML.

[0262] [Formula 16]

[0263]

[0264] [Formula 17]

[0265]

[0266] The characteristics of the OLEDs manufactured in Comparative Examples 1 and 2 and Examples 1 to 11, namely, voltage (V), external quantum efficiency (EQE), color coordinates (CIE), and lifetime (T 95 ), and are listed in Table 1. At room temperature, the characteristics of the OLED were measured using a current source (KEITHLEY) and a photometer (PR 650). 2 The driving voltage, external quantum efficiency and color coordinates were measured under the conditions of 22.5 mA / cm at 40 °C. 2 The life span T is measured under the conditions of 95 (95% of the time to life).

[0267] Table 1

[0268]

[0269]

[0270] As shown in Table 1, the lifespans of the OLEDs of Ex1 to Ex11 using the light-emitting compound of the present disclosure as a dopant are significantly improved compared to the OLEDs of Ref1 and Ref2.

[0271] Figure 4 is a schematic cross-sectional view showing an OLED having a tandem structure of two light emitting units for an organic light emitting display device according to a first embodiment of the present disclosure.

[0272] like Figure 4 As shown, the OLED D includes a first electrode 160 and a second electrode 164 facing each other, and an organic light emitting layer 162 between the first electrode 160 and the second electrode 164. The organic light emitting layer 162 includes: a first light emitting portion 310, which includes a first EML 320; a second light emitting portion 330, which includes a second EML 340; and a charge generation layer (CGL) 350 between the first light emitting portion 310 and the second light emitting portion 330. Figure 2 The organic light emitting display device 100 includes a red pixel, a green pixel, and a blue pixel, and the OLED D is positioned in the blue pixel.

[0273] One of the first electrode 160 and the second electrode 164 is an anode, and the other of the first electrode 160 and the second electrode 164 is a cathode. In addition, one of the first electrode 160 and the second electrode 164 may be a transparent (or semi-transparent) electrode, and the other of the first electrode 160 and the second electrode 164 may be a reflective electrode.

[0274] The CGL 350 is positioned between the first light emitting portion 310 and the second light emitting portion 330, and the first light emitting portion 310, the CGL 350, and the second light emitting portion 330 are sequentially stacked on the first electrode 160. That is, the first light emitting portion 310 is positioned between the first electrode 160 and the CGL 350, and the second light emitting portion 330 is positioned between the second electrode 164 and the CGL 350.

[0275] The first light emitting portion 310 includes a first EML 320. In addition, the first light emitting portion 310 may further include a first EBL 316 between the first electrode 160 and the first EML 320 and a first HBL 318 between the first EML 320 and the CGL 350.

[0276] In addition, the first light emitting portion 310 may further include a first HTL 314 between the first electrode 160 and the first EBL 316 , and a HIL 312 between the first electrode 160 and the first HTL 314 .

[0277] The first EML 320 includes the light-emitting compound in Formula 1 as the first compound 322 and provides blue light emission. For example, the first compound 322 in the first EML 320 may be one of the compounds in Formula 4.

[0278] The EML 320 may further include a second compound 324. For example, the second compound 324 may be represented by Formula 5 and may be one of the compounds in Formula 6.

[0279] In the first EML 320, the first compound 322 has a weight less than the second compound 324. The first compound 322 may act as a dopant (luminescent body), and the second compound 324 may act as a host. For example, in the first EML 320, the weight % of the first compound 322 may be about 0.1 wt % to 30 wt %. In order to provide sufficient luminous efficiency and life, the weight % of the first compound 322 may be about 0.1 wt % to 10 wt %, preferably about 1 wt % to 5 wt %.

[0280] The first EBL 316 may include the compound of Formula 7 as an electron blocking material. In addition, the first HBL 318 may include at least one of the compounds of Formula 9 and Formula 11-1 or Formula 11-2 as a hole blocking material.

[0281] The second light emitting portion 330 includes a second EML 340. In addition, the second light emitting portion 330 may further include a second EBL 334 between the CGL 350 and the second EML 340 and a second HBL 336 between the second EML 340 and the second electrode 164.

[0282] In addition, the second light emitting portion 330 may further include a second HTL 332 between the CGL 350 and the second EBL 334 , and an EIL 338 between the second HBL 336 and the second electrode 164 .

[0283] The second EML 340 includes the light emitting compound in Formula 1 as the third compound 342 and provides blue light emission. For example, the third compound 342 in the second EML 340 may be one of the compounds in Formula 4.

[0284] The second EML 340 may further include a fourth compound 344. For example, the fourth compound 344 may be represented by Formula 5 and may be one of the compounds in Formula 6.

[0285] In the second EML 340, the third compound 342 may have a weight less than that of the fourth compound 344. In the second EML 340, the third compound 342 may act as a dopant (luminescent body), and the fourth compound 344 may act as a host. For example, in the second EML 340, the weight % of the third compound 342 is about 0.1 wt % to 30 wt %. In order to provide sufficient luminous efficiency and lifespan, the weight % of the third compound 342 may be about 0.1 wt % to 10 wt %, preferably about 1 wt % to 5 wt %.

[0286] The third compound 342 in the second EML 340 and the first compound 322 in the first EML 320 may be the same or different, and the fourth compound 344 in the second EML 340 and the second compound 324 in the first EML 320 may be the same or different. In addition, the weight % of the first compound 322 in the first EML 320 and the weight % of the third compound 342 in the second EML 340 may be the same or different.

[0287] The second EBL 334 may include the electron blocking material of Formula 7. In addition, the second HBL 336 may include the hole blocking material of Formula 9 and at least one of the hole blocking materials of Formula 11-1 or Formula 11-2.

[0288] The CGL 350 is positioned between the first light emitting portion 310 and the second light emitting portion 330. That is, the first light emitting portion 310 and the second light emitting portion 330 are connected through the CGL 350. The CGL 350 may be a PN junction CGL of an N-type CGL 352 and a P-type CGL 354.

[0289] The N-type CGL 352 is positioned between the first HBL 318 and the second HTL 332 , and the P-type CGL 354 is positioned between the N-type CGL 352 and the second HTL 332 .

[0290] In the OLED D, since the first EML 320 and the second EML 340 each include the light-emitting compound in Formula 1 as the first compound 322 and the third compound 342 , respectively, the light emission efficiency and lifespan of the OLED D and the organic light-emitting display device 100 are improved.

[0291] In addition, since the first light emitting portion 310 and the second light emitting portion 330 for emitting blue light are stacked, the organic light emitting display device 100 provides an image having a high color temperature.

[0292] Figure 5 is a schematic cross-sectional view showing an organic light emitting display device according to a second embodiment of the present disclosure, and Figure 6 is a schematic cross-sectional view showing an OLED having a tandem structure of two light emitting parts for an organic light emitting display device according to a second embodiment of the present disclosure. Figure 7 is a schematic cross-sectional view showing an OLED having a tandem structure of three light emitting parts for an organic light emitting display device according to a second embodiment of the present disclosure.

[0293] like Figure 5As shown in the figure, the organic light-emitting display device 400 includes: a first substrate 410 in which red pixels RP, green pixels GP and blue pixels BP are defined; a second substrate 470 facing the first substrate 410; an OLED D positioned between the first substrate 410 and the second substrate 470 and providing white light emission; and a color filter layer 480 between the OLED D and the second substrate 470.

[0294] The first substrate 410 and the second substrate 470 may each be a glass substrate or a flexible substrate. For example, the first substrate 410 and the second substrate 470 may each be a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylene naphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate, or a polycarbonate (PC) substrate.

[0295] A buffer layer 420 is formed on the substrate, and a 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 420. The buffer layer 420 may be omitted.

[0296] A semiconductor layer 422 is formed on the buffer layer 420. The semiconductor layer 422 may include an oxide semiconductor material or polysilicon.

[0297] A gate insulating layer 424 is formed on the semiconductor layer 422. The gate insulating layer 424 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride.

[0298] A gate electrode 430 made of a conductive material (eg, metal) is formed on the gate insulating layer 424 corresponding to the center of the semiconductor layer 422 .

[0299] An interlayer insulating layer 432 formed of an insulating material is formed on the gate electrode 430. The interlayer insulating layer 432 may be formed of an inorganic insulating material (eg, silicon oxide or silicon nitride) or an organic insulating material (eg, benzocyclobutene or photo acryl).

[0300] The interlayer insulating layer 432 includes a first contact hole 434 and a second contact hole 436 exposing both sides of the semiconductor layer 422. The first contact hole 434 and the second contact hole 436 are positioned at both sides of the gate electrode 430 to be spaced apart from the gate electrode 430.

[0301] A source electrode 440 and a drain electrode 442 formed of a conductive material (eg, metal) are formed on the interlayer insulating layer 432 .

[0302] The source electrode 440 and the drain electrode 442 are spaced apart from each other with respect to the gate electrode 430 and contact both sides of the semiconductor layer 422 through the first contact hole 434 and the second contact hole 436 , respectively.

[0303] The semiconductor layer 422, the gate electrode 430, the source electrode 440, and the drain electrode 442 constitute a TFT Tr. The TFT Tr is used as a driving element. That is, the TFT Tr may correspond to ( Figure 1 ) driving TFT Td.

[0304] Although not shown, the gate lines and the data lines cross each other to define pixels, and a switching TFT is formed to be connected to the gate lines and the data lines. The switching TFT is connected to a TFT Tr as a driving element.

[0305] In addition, a power supply line may be formed to be parallel to and spaced apart from one of the gate line and the data line, and a storage capacitor for maintaining a voltage of a gate electrode of the TFT Tr in one frame may be further formed.

[0306] A passivation layer 450 is formed to cover the TFT Tr, and includes a drain contact hole 452 exposing the drain electrode 442 of the TFT Tr.

[0307] The first electrode 460 connected to the drain electrode 442 of the TFT Tr through the drain contact hole 452 is separately formed in each pixel and on the passivation layer 450. The first electrode 460 may be an anode and may be formed of a conductive material having a relatively high work function, such as a transparent conductive oxide (TCO). For example, the first electrode 460 may be formed of indium-tin-oxide (ITO), indium-zinc-oxide (IZO), indium-tin-zinc-oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium-copper-oxide (ICO) or aluminum-zinc-oxide (Al:ZnO, AZO).

[0308] When the organic light-emitting display device 400 operates in a bottom emission mode, the first electrode 460 may have a single-layer structure of a transparent conductive material layer. When the organic light-emitting display device 400 operates in a top emission mode, a reflective electrode or a reflective layer may be formed under the first electrode 460. 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 460 may have a three-layer structure of ITO / Ag / ITO or ITO / APC / ITO.

[0309] A bank layer 466 is formed on the passivation layer 450 to cover the edge of the first electrode 460. That is, the bank layer 466 is positioned at the boundary of the pixel and exposes the center of the first electrode 460 in the pixel. Since the OLED D emits white light in the red pixel RP, the green pixel GP, and the blue pixel BP, the organic light emitting layer 462 may be formed as a common layer in the red pixel RP, the green pixel GP, and the blue pixel BP without being separated. The bank layer 466 may be formed to prevent current leakage at the edge of the first electrode 460, and may be omitted.

[0310] An organic light emitting layer 462 is formed on the first electrode 460 .

[0311] Reference Figure 6 , the OLED D includes a first electrode 460 and a second electrode 464 facing each other and an organic light emitting layer 462 between the first electrode 460 and the second electrode 464. The organic light emitting layer 462 includes: a first light emitting portion 710 including a first EML 720; a second light emitting portion 730 including a second EML 740; and a charge generation layer (CGL) 750 between the first light emitting portion 710 and the second light emitting portion 730.

[0312] The first electrode 460 may be formed of a conductive material having a relatively high work function to serve as an anode for injecting holes into the organic light emitting layer 462. The second electrode 464 may be formed of a conductive material having a relatively low work function to serve as a cathode for injecting electrons into the organic light emitting layer 462.

[0313] The CGL 750 is positioned between the first light emitting portion 710 and the second light emitting portion 730, which are sequentially stacked on the first electrode 460. That is, the first light emitting portion 710 is positioned between the first electrode 460 and the CGL 750, and the second light emitting portion 730 is positioned between the second electrode 464 and the CGL 750.

[0314] The first light emitting portion 710 includes a first EML 720. In addition, the first light emitting portion 710 may further include a first EBL 716 between the first electrode 460 and the first EML 720 and a first HBL 718 between the first EML 720 and the CGL 750.

[0315] In addition, the first light emitting portion 710 may further include a first HTL 714 between the first electrode 460 and the first EBL 716 , and a HIL 712 between the first electrode 460 and the first HTL 714 .

[0316] The first EML 720 includes the luminescent compound in Formula 1 as the first compound 722 and provides blue luminescence. For example, the first compound 722 in the first EML 720 may be one of the compounds in Formula 4.

[0317] The EML 720 may further include a second compound 724. For example, the second compound 724 may be represented by Formula 5 and may be one of the compounds in Formula 6.

[0318] In the first EML 720, the first compound 722 has a weight less than the second compound 724. The first compound 722 may act as a dopant (luminescent body), and the second compound 724 may act as a host. For example, in the first EML 720, the weight % of the first compound 722 may be about 0.1 wt % to 30 wt %. In order to provide sufficient luminous efficiency and life, the weight % of the first compound 722 may be about 0.1 wt % to 10 wt %, preferably 1 wt % to 5 wt %.

[0319] The first EBL 716 may include, as an electron blocking material, a compound of Formula 7. In addition, the first HBL 718 may include, as a hole blocking material, at least one of the compounds of Formula 9 and Formula 11-1 or Formula 11-2.

[0320] The second light emitting portion 730 includes a second EML 740. In addition, the second light emitting portion 730 may further include a second EBL 734 between the CGL 750 and the second EML 740 and a second HBL 736 between the second EML 740 and the second electrode 464.

[0321] In addition, the second light emitting portion 730 may further include a second HTL 732 between the CGL 750 and the second EBL 734 , and an EIL 738 between the second HBL 736 and the second electrode 464 .

[0322] The second EML 740 may be a yellow-green EML. For example, the second EML 740 may include a yellow-green dopant 743 and a host 745. The yellow-green dopant 743 may be one of a yellow-green fluorescent compound, a yellow-green phosphorescent compound, and a yellow-green delayed fluorescent compound.

[0323] In the second EML 740, the weight % of the host 745 may be about 70 wt % to 99.9 wt %, and the weight % of the yellow-green dopant 743 may be about 0.1 wt % to 30 wt %. In order to provide sufficient light emitting efficiency, the weight % of the yellow-green dopant 743 may be about 0.1 wt % to 10 wt %, preferably about 1 to 5 wt %.

[0324] The second EBL 734 may include the compound of Formula 7 as an electron blocking material. In addition, the second HBL 736 may include at least one of the compounds of Formula 9 and Formula 11-1 or Formula 11-2 as a hole blocking material.

[0325] The CGL 750 is positioned between the first light emitting portion 710 and the second light emitting portion 730. That is, the first light emitting portion 710 and the second light emitting portion 730 are connected through the CGL 750. The CGL 750 may be a PN junction CGL of an N-type CGL 752 and a P-type CGL 754.

[0326] The N-type CGL 752 is positioned between the first HBL 718 and the second HTL 732 , and the P-type CGL 754 is positioned between the N-type CGL 752 and the second HTL 732 .

[0327] exist Figure 6 In the embodiment, the first EML 720 positioned between the first electrode 460 and the CGL 750 includes a first compound 722 which is a light-emitting compound of the present disclosure and a second compound 724 which is an anthracene derivative, and the second EML 740 positioned between the second electrode 464 and the CGL 750 is a yellow-green EML. Alternatively, the first EML 720 positioned between the first electrode 460 and the CGL 750 may be a yellow-green EML, and the second EML 740 positioned between the second electrode 464 and the CGL 750 may include a light-emitting compound of the present disclosure and an anthracene derivative to become a blue EML.

[0328] In the OLED D, since the first EML 720 or the second EML 740 includes the light-emitting compound 722 of the present disclosure, the light-emitting efficiency and lifespan of the OLED D and the organic light-emitting display device 400 are significantly improved.

[0329] The OLED D including the first light emitting portion 710 providing blue light emission and the second light emitting portion 730 providing yellow-green light emission emits white light.

[0330] Reference Figure 7 The organic light-emitting layer 462 includes: a first light-emitting portion 530, which includes a first EML 520; a second light-emitting portion 550, which includes a second EML 540; a third light-emitting portion 570, which includes a third EML 560; a first CGL 580 between the first light-emitting portion 530 and the second light-emitting portion 550; and a second CGL 590 between the second light-emitting portion 550 and the third light-emitting portion 570.

[0331] The first CGL 580 is positioned between the first light emitting portion 530 and the second light emitting portion 550, and the second CGL 590 is positioned between the second light emitting portion 550 and the third light emitting portion 570. That is, the first light emitting portion 530, the first CGL 580, the second light emitting portion 550, the second CGL 590, and the third light emitting portion 570 are sequentially stacked on the first electrode 460. In other words, the first light emitting portion 530 is positioned between the first electrode 460 and the first CGL 580, the second light emitting portion 550 is positioned between the first CGL 580 and the second CGL 590, and the third light emitting portion 570 is positioned between the second electrode 464 and the second CGL 590.

[0332] The first light emitting portion 530 may include a HIL 532, a first HTL 534, a first EBL 536, a first EML 520, and a first HBL 538 sequentially stacked on the first electrode 460. For example, the HIL 532, the first HTL 534, and the first EBL 536 are positioned between the first electrode 460 and the first EML 520, and the first HBL 538 is positioned between the first EML 520 and the first CGL 580.

[0333] The first EML 520 includes the light emitting compound in Formula 1 as the first compound 522 and provides blue light emission. For example, the first compound 522 in the first EML 520 may be one of the compounds in Formula 4.

[0334] The first EML 520 may further include a second compound 524. For example, the second compound 524 may be represented by Formula 5 and may be one of the compounds in Formula 6.

[0335] In the first EML 520, the first compound 522 has a weight less than the second compound 524. The first compound 522 may act as a dopant (luminescent body), and the second compound 524 may act as a host. For example, in the first EML 520, the weight % of the first compound 522 may be about 0.1 wt % to 30 wt %. In order to provide sufficient luminous efficiency and life, the weight % of the first compound 522 may be about 0.1 wt % to 10 wt %, preferably about 1 wt % to 5 wt %.

[0336] The first EBL 536 may include the compound of Formula 7 as an electron blocking material. In addition, the first HBL 538 may include at least one of the compounds of Formula 9 and Formula 11-1 or Formula 11-2 as a hole blocking material.

[0337] The second light emitting portion 550 may include a second HTL 552, a second EML 540, and an electron transport layer (ETL) 554. The second HTL 552 is positioned between the first CGL 580 and the second EML 540, and the ETL 554 is positioned between the second EML 540 and the second CGL 590.

[0338] The second EML 540 may be a yellow-green EML. For example, the second EML 540 may include a host and a yellow-green dopant.

[0339] Alternatively, the second EML 540 may include a host, a red dopant, and a green dopant. In this case, the second EML 540 may have a single-layer structure or a double-layer structure having a lower layer including a host and a red dopant (or a green dopant) and an upper layer including a host and a green dopant (or a red dopant).

[0340] The second EML 540 may have a triple-layer structure of a first layer including a host and a red dopant, a second layer including a host and a yellow-green dopant, and a third layer including a host and a green dopant.

[0341] The third light emitting portion 570 may include a third HTL 572 , a second EBL 574 , a third EML 560 , a second HBL 576 , and an EIL 578 .

[0342] The third EML 560 includes the light emitting compound in Formula 1 as the third compound 562 and provides blue light emission. For example, the third compound 562 in the third EML 560 may be one of the compounds in Formula 4.

[0343] The third EML 560 may further include a fourth compound 564. For example, the fourth compound 564 may be represented by Formula 5, and may be one of the compounds in Formula 6.

[0344] In the third EML 560, the third compound 562 may have a weight percentage less than that of the fourth compound 564. In the third EML 560, the third compound 562 may act as a dopant (luminescent body), and the fourth compound 564 may act as a host. For example, in the third EML 560, the weight percentage of the third compound 562 is about 0.1 weight % to 30 weight %. In order to provide sufficient luminous efficiency and lifespan, the weight percentage of the third compound 562 may be about 0.1 weight % to 10 weight %, preferably about 1 weight % to 5 weight %.

[0345] The third compound 562 in the third EML 560 and the first compound 522 in the first EML 520 may be the same or different, and the fourth compound 564 in the third EML 560 and the second compound 524 in the first EML 520 may be the same or different. In addition, the weight % of the first compound 522 in the first EML 520 and the weight % of the third compound 562 in the third EML 560 may be the same or different.

[0346] The second EBL 574 may include the electron blocking material of Formula 7. In addition, the second HBL 576 may include the hole blocking material of Formula 9 and at least one of the hole blocking materials of Formula 11-1 or Formula 11-2.

[0347] The first CGL 580 is positioned between the first light emitting portion 530 and the second light emitting portion 550, and the second CGL 590 is positioned between the second light emitting portion 550 and the third light emitting portion 570. That is, the first light emitting portion 530 and the second light emitting portion 550 are connected through the first CGL 580, and the second light emitting portion 550 and the third light emitting portion 570 are connected through the second CGL 590. The first CGL 580 may be a PN junction CGL of a first N-type CGL 582 and a first P-type CGL 584, and the second CGL 590 may be a PN junction CGL of a second N-type CGL 592 and a second P-type CGL 594.

[0348] In the first CGL 580 , a first N-type CGL 582 is positioned between the first HBL 538 and the second HTL 552 , and a first P-type CGL 584 is positioned between the first N-type CGL 582 and the second HTL 552 .

[0349] In the second CGL 590 , the second N-type CGL 592 is positioned between the ETL 554 and the third HTL 572 , and the second P-type CGL 594 is positioned between the second N-type CGL 592 and the third HTL 572 .

[0350] In the OLED D, since the first EML 520 and the third EML 560 each include the light-emitting compound of Formula 1 as the first compound 522 and the third compound 562, respectively, the light emission efficiency and lifespan of the OLED D and the organic light-emitting display device 400 are improved.

[0351] In addition, the OLED D including the first and third light emitting parts 530 and 570 and the second light emitting part 550 emitting yellow-green light or red / green light may emit white light.

[0352] exist Figure 7In the embodiment, the OLED D has a three-stack structure of a first light emitting portion 530, a second light emitting portion 550, and a third light emitting portion 570. Alternatively, the OLED D may further include another light emitting portion and a CGL.

[0353] Refer again Figure 5 A second electrode 464 is formed on the substrate 410 on which the organic light emitting layer 462 is formed.

[0354] In the organic light emitting display device 400 , since light emitted from the organic light emitting layer 462 is incident to the color filter layer 480 through the second electrode 464 , the second electrode 464 has a thin profile to transmit the light.

[0355] The first electrode 460 , the organic light emitting layer 462 , and the second electrode 464 constitute an OLED D.

[0356] The color filter layer 480 is positioned above the OLED D and includes a red color filter 482, a green color filter 484, and a blue color filter 486 corresponding to the red pixel RP, the green pixel GP, and the blue pixel BP, respectively. The red color filter 482 may include at least one of a red dye and a red pigment, the green color filter 484 may include at least one of a green dye and a green pigment, and the blue color filter 486 may include at least one of a blue dye and a blue pigment.

[0357] Although not shown, the color filter layer 480 may be attached to the OLED D by using an adhesive layer. Alternatively, the color filter layer 480 may be directly formed on the OLED D.

[0358] 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.

[0359] A polarizing plate (not shown) for reducing ambient light reflection may be disposed above the top emission type OLED D. For example, the polarizing plate may be a circular polarizing plate.

[0360] exist Figure 5 In the OLED D, the first electrode 460 and the second electrode 464 are respectively a reflective electrode and a transparent (or semi-transparent) electrode, and the color filter layer 480 is arranged above the OLED D. Alternatively, when the first electrode 460 and the second electrode 464 are respectively a transparent (or semi-transparent) electrode and a reflective electrode, the color filter layer 480 may be arranged between the OLED D and the first substrate 410.

[0361] A color conversion layer (not shown) may be formed between the OLED D and the color filter layer 480. The color conversion layer may include a red color conversion layer, a green color conversion layer, and a blue color conversion layer corresponding to the red pixel RP, the green pixel GP, and the blue pixel BP, respectively. White light from the OLED D is converted into red light, green light, and blue light by the red color conversion layer, the green color conversion layer, and the blue color conversion layer, respectively. For example, the color conversion layer may include quantum dots. Therefore, the color purity of the organic light emitting display device 400 may be further improved.

[0362] A color conversion layer may be included instead of the color filter layer 480 .

[0363] As described above, in the organic light emitting display device 400, the OLED D in the red pixel RP, the green pixel GP, and the blue pixel BP emits white light, and the white light from the organic light emitting diode D passes through the red filter 482, the green filter 484, and the blue filter 486. Therefore, red light, green light, and blue light are provided by the red pixel RP, the green pixel GP, and the blue pixel BP, respectively.

[0364] exist Figures 5 to 7 In the embodiment, the OLED D emitting white light is used for a display device. Alternatively, for use in a lighting device, 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. A display device and a lighting device each including the OLED D of the present disclosure may be referred to as an organic light emitting device.

[0365] Figure 8 is a schematic cross-sectional view showing an organic light emitting display device according to a third embodiment of the present disclosure.

[0366] like Figure 8 As shown, the organic light-emitting display device 600 includes: a first substrate 610 in which red pixels RP, green pixels GP and blue pixels BP are defined; a second substrate 670 facing the first substrate 610; an OLED D positioned between the first substrate 610 and the second substrate 670 and providing white light emission; and a color conversion layer 680 between the OLED D and the second substrate 670.

[0367] Although not shown, a color filter may be formed between the second substrate 670 and each color conversion layer 680 .

[0368] The first substrate 610 and the second substrate 670 may each be a glass substrate or a flexible substrate. For example, the first substrate 610 and the second substrate 670 may each be a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylene naphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate, or a polycarbonate (PC) substrate.

[0369] A TFT Tr corresponding to each of the red pixel RP, the green pixel GP, and the blue pixel BP is formed on the first substrate 610 , and a passivation layer 650 having a drain contact hole 652 exposing an electrode, eg, a drain electrode, of the TFT Tr is formed to cover the TFT Tr.

[0370] An OLED including a first electrode 660, an organic light emitting layer 662, and a second electrode 664 is formed on the passivation layer 650. In this case, the first electrode 660 may be connected to the drain electrode of the TFT Tr through the drain contact hole 652.

[0371] A bank layer 666 is formed on the passivation layer 650 to cover the edge of the first electrode 660. That is, the bank layer 666 is positioned at the boundary of the pixel and exposes the center of the first electrode 660 in the pixel. Since the OLED D emits blue light in the red pixel RP, the green pixel GP, and the blue pixel BP, the organic light emitting layer 662 may be formed as a common layer in the red pixel RP, the green pixel GP, and the blue pixel BP without being separated. The bank layer 666 may be formed to prevent current leakage at the edge of the first electrode 660, and may be omitted.

[0372] OLED D emits blue light and may have Figure 3 or Figure 4 That is, the OLED D is formed in each of the red pixel RP, the green pixel GP, and the blue pixel BP and provides blue light.

[0373] The color conversion layer 680 includes a first color conversion layer 682 corresponding to the red pixel RP and a second color conversion layer 684 corresponding to the green pixel GP. For example, the color conversion layer 680 may include an inorganic color conversion material such as quantum dots. The color conversion layer 680 does not exist in the blue pixel BP, so that the OLED D in the blue pixel BP can directly face the second substrate 670.

[0374] The blue light from the OLED D is converted into red light by the first color conversion layer 682 in the red pixel RP, and the blue light from the OLED D is converted into green light by the second color conversion layer 684 in the green pixel GP.

[0375] Therefore, the organic light emitting display device 600 can display a full-color image.

[0376] On the other hand, when light from the OLED D passes through the first substrate 610 , the color conversion layer 680 is disposed between the OLED D and the first substrate 610 .

[0377] It will be apparent to those skilled in the art that various modifications and changes may be made to the embodiments of the present disclosure without departing from the spirit or scope of the present disclosure. Therefore, it is intended that modifications and changes cover the present disclosure as long as they fall within the scope of the appended claims and their equivalents.

Claims

1. A luminescent compound represented by formula 2-2 or 3-2: [Formula 2-2] [Formula 3-2] In formulas 2-2 and 3-2, Y3 is O or S, R1 is selected from hydrogen, deuterium, C1-C10 alkyl which is unsubstituted or substituted by deuterium, C6-C30 arylamine which is unsubstituted or substituted by deuterium or C1-C10 alkyl, C6-C30 aryl which is unsubstituted or substituted by deuterium or C1-C10 alkyl, and C5-C30 heteroaryl which is unsubstituted or substituted by deuterium or C1-C10 alkyl, wherein in formula 2-2, two adjacent ones of R4 to R7 are connected to each other to form a benzene ring, and the other two of R4 to R7 are each independently selected from hydrogen, deuterium, C1 to C10 alkyl groups which are unsubstituted or substituted with deuterium, C6 to C30 arylamine groups which are unsubstituted or substituted with deuterium or C1 to C10 alkyl, C6 to C30 aryl groups which are unsubstituted or substituted with deuterium or C1 to C10 alkyl, and C5 to C30 heteroaryl groups which are unsubstituted or substituted with deuterium or C1 to C10 alkyl, R 21 To R 27 are each independently selected from hydrogen, deuterium, C1-C10 alkyl which is unsubstituted or substituted by deuterium, C6-C30 arylamine which is unsubstituted or substituted by deuterium or C1-C10 alkyl, C6-C30 aryl which is unsubstituted or substituted by deuterium or C1-C10 alkyl, and C5-C30 heteroaryl which is unsubstituted or substituted by deuterium or C1-C10 alkyl, Wherein in Formula 3-2, R8 and R9, or two adjacent ones of R4 to R7 are connected to each other to form a benzene ring, The rest of R4 to R7, R8 and R9 are each independently selected from hydrogen, deuterium, C1 to C10 alkyl which is unsubstituted or substituted by deuterium, C6 to C30 arylamine which is unsubstituted or substituted by deuterium or C1 to C10 alkyl, C6 to C30 aryl which is unsubstituted or substituted by deuterium or C1 to C10 alkyl, and C5 to C30 heteroaryl which is unsubstituted or substituted by deuterium or C1 to C10 alkyl, R 31 To R 37 and are each independently selected from hydrogen, deuterium, C1-C10 alkyl unsubstituted or substituted with deuterium, C6-C30 arylamine unsubstituted or substituted with deuterium or C1-C10 alkyl, C6-C30 aryl unsubstituted or substituted with deuterium or C1-C10 alkyl, and C5-C30 heteroaryl unsubstituted or substituted with deuterium or C1-C10 alkyl.

2. The luminescent compound according to claim 1, wherein the luminescent compound is one of the compounds in Formula 4-1: [Formula 4-1] 3. A luminescent compound represented by formula 3-4: [Formula 3-4] Wherein in the formula 3-4, Y3 is O or S, Y4 is O or S, R1 is selected from hydrogen, deuterium, C1-C10 alkyl which is unsubstituted or substituted by deuterium, C6-C30 arylamine which is unsubstituted or substituted by deuterium or C1-C10 alkyl, C6-C30 aryl which is unsubstituted or substituted by deuterium or C1-C10 alkyl, and C5-C30 heteroaryl which is unsubstituted or substituted by deuterium or C1-C10 alkyl, R 41 To R 43 are each independently selected from hydrogen, deuterium, C1-C10 alkyl which is unsubstituted or substituted by deuterium, C6-C30 arylamine which is unsubstituted or substituted by deuterium or C1-C10 alkyl, C6-C30 aryl which is unsubstituted or substituted by deuterium or C1-C10 alkyl, and C5-C30 heteroaryl which is unsubstituted or substituted by deuterium or C1-C10 alkyl, R 14 and R 15 , or R 10 To R 13 The two adjacent ones are connected to each other to form a benzene ring, R 14 and R 15 , R 10 To R 13 The rest of the residues are each independently selected from hydrogen, deuterium, C1 to C10 alkyl which is unsubstituted or substituted by deuterium, C6 to C30 arylamine which is unsubstituted or substituted by deuterium or C1 to C10 alkyl, C6 to C30 aryl which is unsubstituted or substituted by deuterium or C1 to C10 alkyl, and C5 to C30 heteroaryl which is unsubstituted or substituted by deuterium or C1 to C10 alkyl, R8 and R9, or two adjacent ones of R4 to R7, are connected to each other to form a benzene ring, and the rest of R4 to R7, R8 and R9 are each independently selected from hydrogen, deuterium, C1 to C10 alkyl groups which are unsubstituted or substituted with deuterium, C6 to C30 arylamine groups which are unsubstituted or substituted with deuterium or C1 to C10 alkyl, C6 to C30 aryl groups which are unsubstituted or substituted with deuterium or C1 to C10 alkyl, and C5 to C30 heteroaryl groups which are unsubstituted or substituted with deuterium or C1 to C10 alkyl.

4. The luminescent compound according to claim 3, wherein the luminescent compound is one of the compounds in Formula 4-2: [Formula 4-2] 5. An organic light-emitting device, comprising: substrate; and An organic light emitting diode positioned on the substrate and comprising: a first electrode; a second electrode facing the first electrode; and a first light emitting material layer containing a first compound and positioned between the first electrode and the second electrode, The first compound is the luminescent compound according to any one of claims 1 to 4.

6. The organic light-emitting device according to claim 5, wherein the first light-emitting material layer further comprises a second compound, The second compound is represented by Formula 5: [Formula 5] wherein Ar1 and Ar2 are each independently a C6 to C30 aryl group or a C5 to C30 heteroaryl group, L is a single bond or a C6 to C30 arylene group, and The hydrogen in the second compound is undeuterated or partially or fully deuterated.

7. The organic light-emitting device according to claim 6, wherein the second compound is one of the compounds in Formula 6: [Formula 6] 8. The organic light emitting device according to claim 5, wherein the organic light emitting diode further comprises: a second light-emitting material layer, the second light-emitting material layer comprising a third compound and positioned between the first light-emitting material layer and the second electrode; and a first charge generation layer, the first charge generation layer being between the first light emitting material layer and the second light emitting material layer, and The third compound is the luminescent compound according to any one of claims 1 to 4.

9. The organic light emitting device according to claim 5, 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 conversion layer is disposed between the substrate and the organic light emitting diode, or on the organic light emitting diode and corresponds to the red pixel and the green pixel.

10. The organic light emitting device according to claim 8, wherein the organic light emitting diode further comprises: a third light emitting material layer positioned between the first charge generation layer and the second light emitting material layer; as well as a second charge generation layer, the second charge generation layer being between the second light emitting material layer and the third light emitting material layer, and The third luminescent material layer emits yellow-green light or red light and green light.

11. The organic light emitting device according to claim 5, wherein the organic light emitting diode further comprises: a second light emitting material layer, the second light emitting material layer emitting yellow-green light and positioned between the first light emitting material layer and the second electrode; A charge generation layer is between the first light emitting material layer and the second light emitting material layer.

12. The organic light emitting device according to claim 5, 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 disposed between the substrate and the organic light emitting diode, or on the organic light emitting diode and corresponds to the red pixel, the green pixel, and the blue pixel.

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