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

Abstract

The present disclosure relates to a light-emitting compound and an organic light-emitting device including the same as follows.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of Korean Patent Application No. 10-2020-0186022 filed in Korea on December 29, 2020, which is hereby incorporated by reference in its 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 light-emitting compound. 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] By injecting electrons from the cathode as an electron injection electrode and holes from the anode as a hole injection electrode into the light-emitting material layer (EML), the electrons are combined with the holes to generate excitons, and the excitons are converted from an excited state to a ground state, so that the OLED emits light. A flexible substrate (such as a plastic substrate) can be used as a base substrate for forming an element. In addition, the organic light-emitting display device can operate at a voltage (such as 10V or less) lower than the voltage required for other display devices to operate. 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 does not provide sufficient light emitting efficiency and lifespan, so that the organic light emitting display device is limited in terms of light emitting efficiency and lifespan. Summary of the invention

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

[0009] Additional features and advantages of the present disclosure are set forth in the following description and will become apparent from the description or become apparent through the practice of the present disclosure. The purpose 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 embodiments of the present disclosure, as described herein, one aspect of the present disclosure is a luminescent compound represented by Formula 1: [Formula 1]

[0011]

[0012] 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 Z1 to Z4 are each independently N or CR4, and at least three of Z1 to Z4 are CR4, wherein R1 to R3 are each independently selected from hydrogen, deuterium, C1 to C10 alkyl which is unsubstituted or substituted by deuterium, C6 to C30 arylamino 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 , wherein R4 to R6 are each independently selected from hydrogen, deuterium, C1 to C10 alkyl groups which are unsubstituted or substituted with deuterium, C6 to C30 arylamino 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 adjacent two of R4 to R6 are connected to each other to form a condensed ring, and at least one of R4 to R6 is C1 to C10 alkyl groups which are substituted with deuterium, and wherein Ring A and Ring B 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 six-membered heteroaromatic ring.

[0013] Another aspect of the present disclosure is an organic light-emitting device, comprising: a substrate; and an organic light-emitting diode, located on the substrate and comprising a first electrode, a second electrode facing the first electrode, and a first light-emitting material layer comprising a first compound and located between the first electrode and the second electrode, wherein the first compound is the above-mentioned light-emitting compound.

[0014] 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

[0015] The present disclosure includes accompanying drawings to provide a further understanding of the present disclosure, and the accompanying drawings are incorporated in and constitute a part of this specification. The accompanying drawings illustrate embodiments of the present disclosure and together with the description serve to explain the principles of the present disclosure.

[0016] Figure 1 is a schematic circuit diagram showing an organic light emitting display device of the present disclosure.

[0017] Figure 2 is a schematic cross-sectional view showing an organic light emitting display device according to a first embodiment of the present disclosure.

[0018] Figure 3 is a schematic cross-sectional view showing an OLED having a single light emitting portion of an organic light emitting display device according to a first embodiment of the present disclosure.

[0019] Figure 4 1 is a schematic cross-sectional view showing an OLED having a tandem structure of two light emitting parts of an organic light emitting display device according to a first embodiment of the present disclosure.

[0020] Figure 5 is a schematic cross-sectional view showing an organic light emitting display device according to a second embodiment of the present disclosure.

[0021] Figure 6 1 is a schematic cross-sectional view showing an OLED having a tandem structure of two light emitting parts of an organic light emitting display device according to a second embodiment of the present disclosure.

[0022] Figure 7 2 is a schematic cross-sectional view showing an OLED having a series structure of three light-emitting portions of an organic light-emitting display device according to a second embodiment of the present disclosure.

[0023] Figure 8 is a schematic cross-sectional view showing an organic light emitting display device according to a third embodiment of the present disclosure. Specific embodiments

[0024] Reference will now be made in detail to some examples and preferred embodiments which are illustrated in the accompanying drawings.

[0025] Figure 1 is a schematic circuit diagram showing an organic light emitting display device of the present disclosure.

[0026] like Figure 1 As shown, in the organic light emitting display device, gate lines GL and data lines DL are formed to cross each other to define pixels (pixel regions) P, and power lines PL are formed. A switching thin film transistor (TFT) Ts, a driving 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.

[0027] 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 the gate of the driving thin film transistor Td and one electrode of the storage capacitor Cst through the switching thin film transistor Ts.

[0028] The driving thin film transistor Td is turned on by the data signal applied to the gate, so that a current proportional to the data signal is supplied from the power line PL to the OLED D through the driving thin film transistor Td. The OLED D emits light having 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 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.

[0029] Figure 2 is a schematic cross-sectional view showing an organic light emitting display device according to a first embodiment of the present disclosure.

[0030] like Figure 2 As shown, the organic light emitting display device 100 includes a substrate 110, a TFT Tr, and an OLED D connected to the TFT Tr. For example, the organic light emitting display device 100 may include a red pixel, a green pixel, and a blue pixel, and the OLED D may be formed in each of the red pixel, the green pixel, and the blue pixel. That is, the OLED D emitting red light, green light, and blue light may be respectively provided in the red pixel, the green pixel, and the blue pixel.

[0031] 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.

[0032] The buffer layer 120 is formed on the substrate, and the TFT Tr is formed on the buffer layer 120. The buffer layer 120 may be omitted.

[0033] The semiconductor layer 122 is formed on the buffer layer 120. The semiconductor layer 122 may include an oxide semiconductor material or polysilicon.

[0034] 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 to 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 to both sides of the semiconductor layer 122.

[0035] The 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.

[0036] The gate 130 formed of a conductive material such as metal is formed on the gate insulating layer 124 to correspond to the center of the semiconductor layer 122 .

[0037] exist Figure 2 In the embodiment of the present invention, the gate insulating layer 124 is formed on the entire surface of the substrate 110. Alternatively, the gate insulating layer 124 may be patterned to have the same shape as the gate 130.

[0038] 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 acrylic.

[0039] The interlayer insulating layer 132 includes a first contact hole 134 and a second contact hole 136 exposing both sides of the semiconductor layer 122. The first contact hole 134 and the second contact hole 136 are located at both sides of the gate 130 to be spaced apart from the gate 130.

[0040] 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 130, the first contact hole 134 and the second contact hole 136 are formed through only the interlayer insulating layer 132.

[0041] A source electrode 140 and a drain electrode 142 formed of a conductive material (eg, metal) are formed on the interlayer insulating layer 132 .

[0042] 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.

[0043] 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.

[0044] In the TFT Tr, the gate electrode 130, the source electrode 140, and the drain electrode 142 are located above the semiconductor layer 122. That is, the TFT Tr has a coplanar structure.

[0045] Alternatively, in the TFT Tr, the gate electrode may be located below the semiconductor layer, and the source electrode and the drain electrode may be located above the semiconductor layer, so that the TFT Tr may have an inverted staggered structure. In this case, the semiconductor layer may include amorphous silicon.

[0046] 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.

[0047] In addition, a power supply line which may be formed parallel to and spaced apart from one of the gate line and the data line and a storage capacitor for maintaining a voltage of the gate electrode of the TFT Tr in one frame may be further formed.

[0048] The passivation layer 150 is formed to cover the TFT Tr, and the passivation layer 150 includes a drain contact hole 152 exposing the drain electrode 142 of the TFT Tr.

[0049] The first electrode 160 connected to the drain electrode 142 of the TFT Tr through the drain contact hole 152 is formed in each pixel and on the 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).

[0050] 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.

[0051] The bank layer 166 is formed on the passivation layer 150 to cover the edge of the first electrode 160. That is, in the pixel, the bank layer 166 is located at the boundary of the pixel and exposes the center of the first electrode 160.

[0052] The 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.

[0053] The organic light emitting layer 162 in each of the red pixel, the green pixel and the blue pixel is separated. 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.

[0054] The second electrode 164 is formed over the substrate 110 on which the organic light emitting layer 162 is formed. The second electrode 164 covers the entire surface of the display area and may be formed of a conductive material having a relatively low work function to serve as a cathode. For example, the second electrode 164 may be formed of aluminum (Al), magnesium (Mg), 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-transmitting property).

[0055] The first electrode 160 , the organic light emitting layer 162 , and the second electrode 164 constitute an OLED D.

[0056] The encapsulation film 170 is formed on the second electrode 164 to prevent moisture from penetrating into the OLED D. The encapsulation film 170 includes a first inorganic insulating layer 172 , an organic insulating layer 174 , and a second inorganic insulating layer 176 sequentially stacked, but is not limited thereto. The encapsulation film 170 may be omitted.

[0057] The organic light-emitting display device 100 may further include a polarizing plate (not shown) for reducing ambient light reflection. For example, the polarizing plate may be a circular polarizing plate. In a bottom-emitting organic light-emitting display device 100, the polarizing plate may be disposed below the substrate 110. In a top-emitting organic light-emitting display device 100, the polarizing plate may be disposed on or above the encapsulation film 170.

[0058] 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.

[0059] Figure 3 is a schematic cross-sectional view showing an OLED having a single light emitting unit of an organic light emitting display device according to a first embodiment of the present disclosure.

[0060] 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 between the first electrode 160 and the second electrode 164. 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 located in the blue pixel.

[0061] 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.

[0062] 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 .

[0063] 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 .

[0064] 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 .

[0065] The EML 240 includes a luminescent compound 242 as a first compound. The luminescent compound is a polycyclic aromatic hydrocarbon compound and is represented by Formula 1.

[0066] [Molecular formula 1]

[0067]

[0068] 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. Z1 to Z4 are each independently N or CR4, and at least three of Z1 to Z4 are CR4. 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 arylamino 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. In addition, R4 to R6 are each independently selected from hydrogen, deuterium, C1 to C10 alkyl groups which are not substituted or substituted by deuterium, C6 to C30 arylamino groups which are not substituted or substituted by deuterium or C1 to C10 alkyl groups, C6 to C30 aryl groups which are not substituted or substituted by deuterium or C1 to C10 alkyl groups, and C5 to C30 heteroaryl groups which are not substituted or substituted by deuterium or C1 to C10 alkyl groups, or adjacent two of R4 to R6 are connected (combined) to form a condensed ring. At least one of R4 to R6 is C1 to C10 alkyl groups which are substituted by deuterium.

[0069] The A ring and the B 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 six-membered heteroaromatic ring.

[0070] The condensed ring may be a C6 to C30 aromatic ring or a C5 to C30 heteroaromatic (condensed) ring. For example, the condensed ring of the C6 to C30 aromatic ring may be a benzene ring or a naphthalene ring.

[0071] In each of the A ring and the B ring, hydrogen may be substituted with at least one of D, an unsubstituted or deuterium-substituted C1 to C10 alkyl group, a C6 to C30 aryl group, and a C5 to C30 heteroaryl group.

[0072] For example, in Formula 1, n may be 0. That is, a 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.

[0073] [Molecular formula 2-1]

[0074]

[0075] In addition, in Formula 2-1, X may be B, Y1 and Y2 may each be NR1, and Ring A and Ring B may each be a benzene ring. That is, the light-emitting compound in Formula 1 may be represented by Formula 2-2.

[0076] [Molecular formula 2-2]

[0077]

[0078] In the molecular formula 2-2, one of Z1 to Z4 is N, and three of Z1 to Z4 are CR4. At least one of the three R4 is a C1 to C10 alkyl group substituted with D. 11 To R 17 Each is independently selected from hydrogen, deuterium (D), C1 to C10 alkyl which is unsubstituted or substituted by deuterium, C6 to C30 arylamino 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.

[0079] For example, in Formula 2-2, R1 may be a C6 to C30 aryl group, such as a phenyl group. One of the three R4s may be a C1 to C10 alkyl group substituted with D, such as CD3, and the remaining two of the three R4s may be hydrogen. 11 To R 17The compound of Formula 2-1 or Formula 2-2 may be one of the compounds 1-1 to 1-10 in Formula 6.

[0080] Alternatively, in Formula 1, n may be O, and Z1 to Z4 may be CR4. That is, the light-emitting compound in Formula 1 may be represented by Formula 3-1.

[0081] [Molecular formula 3-1]

[0082]

[0083] In addition, in Formula 3-1, X may be B, Y1 and Y2 may each be NR1, and Ring A and Ring B may each be a benzene ring. That is, the light-emitting compound in Formula 1 may be represented by Formula 3-2.

[0084] [Molecular formula 3-2]

[0085]

[0086] In the molecular formula 3-2, adjacent two of R4 are connected to each other to form a condensed ring, and at least one of the remaining two of R4 is a C1 to C10 alkyl group substituted with D. 21 To R 27 and C5 to C30 heteroaryl groups which are unsubstituted or substituted with deuterium or C1 to C10 alkyl.

[0087] For example, in the molecular formula 3-2, R1 may be a C6 to C30 aromatic group, such as a phenyl group. One of the other two R4s may be C6 to C30, and the other of the other two R4s may be hydrogen. In addition, the condensed ring formed by the adjacent two R4s may be a C6 to C30 aromatic ring, such as a benzene ring, and R 21 To R 27 The compound of Formula 3-1 or Formula 3-2 may be one of the compounds 2-1 to 2-6 in Formula 6.

[0088] Alternatively, in Molecular Formula 1, n may be 1. That is, the light-emitting compound in Molecular Formula 1 may be represented by Molecular Formula 4-1.

[0089] [Molecular formula 4-1]

[0090]

[0091] In addition, in the molecular formula 4-1, X may be B, Y1 and Y2 may each be NR1, and the A ring and the B ring may each be a benzene ring. In this case, the luminescent compound in the molecular formula 4-1 may be represented by one of the molecular formulas 4-2 to 4-4, depending on the bonding position of the five-membered ring including Y3.

[0092] [Molecular formula 4-2]

[0093]

[0094] [Molecular formula 4-3]

[0095]

[0096] [Molecular formula 4-4]

[0097]

[0098] In Formula 4-2 to Formula 4-4, one of Z1 to Z4 is N, and three of Z1 to Z4 are CR4. At least one of the three R4 is a C1 to C10 alkyl group substituted with D. 31 To R 37 Each is independently selected from hydrogen, deuterium (D), C1 to C10 alkyl which is unsubstituted or substituted by deuterium, C6 to C30 arylamino 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.

[0099] For example, in Formula 4-2 to Formula 4-4, R1 may be a C6 to C30 aryl group, such as a phenyl group. One of the three R4s may be a C1 to C10 alkyl group substituted with D, such as CD3, and the remaining two of the three R4s may be hydrogen. 31 To R 37 The compounds of Formula 4-1 to Formula 4-4 may be one of the compounds 3-1 to 3-9 in Formula 6.

[0100] Alternatively, in each of Formula 4-2 to Formula 4-4, R 31 To R 34 Two adjacent ones of may be connected to each other to form a hetero-condensed ring. That is, the light-emitting compound of the present disclosure may be represented by one of Molecular Formula 4-5 to Molecular Formula 4-7.

[0101] [Molecular formula 4-5]

[0102]

[0103] [Molecular formula 4-6]

[0104]

[0105] [Molecular formula 4-7]

[0106]

[0107] In each of Formulae 4-5 to 4-7, Y4 is O or S. One of Z5 to Z8 is N, and the remaining three of Z5 to Z8 are CR7. The three R7s are each independently selected from hydrogen, deuterium, C1 to C10 alkyl which is not substituted or substituted by deuterium, C6 to C30 arylamino which is not substituted or substituted by deuterium or C1 to C10 alkyl, C6 to C30 aryl which is not substituted or substituted by deuterium or C1 to C10 alkyl, and C5 to C30 heteroaryl which is not substituted or substituted by deuterium or C1 to C10 alkyl, and at least one of the three R7s is C1 to C10 alkyl substituted by D.

[0108] R 35 To R 37 Each is independently selected from hydrogen, deuterium (D), C1 to C10 alkyl which is unsubstituted or substituted by deuterium, C6 to C30 arylamino 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.

[0109] For example, in each of Formulae 4-5 to 4-7, R1 may be a C6 to C30 aryl group, such as a phenyl group. One of the three R7s may be a C1 to C10 alkyl group substituted with D, such as CD3, and the other two of the three R7s may be hydrogen. 35 To R 37 It may be hydrogen.

[0110] Alternatively, in Formula 1, n may be 1, and Z1 to Z4 may be CR4. That is, the light-emitting compound in Formula 1 may be represented by Formula 5-1.

[0111] [Molecular formula 5-1]

[0112]

[0113] In addition, in Formula 5-1, X may be B, Y1 and Y2 may each be NR1, and Ring A and Ring B may each be a benzene ring. That is, the light-emitting compound in Formula 1 may be represented by one of Formulas 5-2.

[0114] [Molecular formula 5-2]

[0115]

[0116] In the molecular formula 5-2, adjacent two of four R4 or R5 and R6 are connected to form a condensed ring, and at least one of the remaining four of R4, R5 and R6 is a C1 to C10 alkyl group substituted with D. 41 To R 47 Each is independently selected from hydrogen, deuterium (D), C1 to C10 alkyl which is unsubstituted or substituted by deuterium, C6 to C30 arylamino 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.

[0117] For example, in the molecular formula 5-2, R1 can be a C6 to C30 aromatic group, such as a phenyl group. One of the remaining four of R4, R5 and R6 can be a C1-C10 alkyl group substituted with D, such as CD3, and the other of the remaining four of R4, R5 and R6 can be hydrogen. The condensed ring formed by two adjacent ones of the four R4, R5 and R6 can be a C6 to C30 aromatic ring, such as a benzene ring, and R 41 To R 47 The compound of Formula 5-1 or Formula 5-2 may be one of the compounds 4-1 to 4-4 in Formula 6.

[0118] Alternatively, in the molecular formula 5-1, the A ring may be a benzene ring, and the B ring may be a heteroaromatic condensed ring. That is, the light-emitting compound in the molecular formula 5-1 may be represented by the molecular formula 5-3.

[0119] [Molecular formula 5-3]

[0120]

[0121] In the molecular formula 5-3, Y5 is O or S. Adjacent two of four R4 or R5 and R6 are connected to form a condensed ring, and at least one of the remaining four of R4, R5 and R6 is a C1 to C10 alkyl group substituted with D. R8, R9 and R 51 To R 54 are each independently selected from hydrogen, deuterium (D), C1 to C10 alkyl which is unsubstituted or substituted by deuterium, C6 to C30 arylamino 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, or R 51 To R 54 Two adjacent R8 and R9 in the ring are connected to form a condensed ring. 51 To R 54At least one of the remaining four is a C1 to C10 alkyl group substituted by D. 55 To R 57 Each is independently selected from hydrogen, deuterium (D), C1 to C10 alkyl which is unsubstituted or substituted by deuterium, C6 to C30 arylamino 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.

[0122] In the molecular formula 5-3, X may be B, and Y1 and Y2 may each be NR1. That is, the light-emitting compound in the molecular formula 5-3 may be represented by the molecular formula 5-4.

[0123] [Molecular formula 5-4]

[0124]

[0125] For example, in Formula 5-4, R1 may be a C6 to C30 aryl group, such as a phenyl group. One of the remaining four of R4, R5, and R6 may be a C1 to C10 alkyl group substituted with D, such as CD3, and the other of the remaining four of R4, R5, and R6 may be hydrogen. The condensed ring formed by the four adjacent two of R4 or R5 and R6 and the condensed ring formed by R 51 To R 54 The adjacent two or fused rings formed by R8 and R9 in each of the above may be C6 to C30 aromatic rings, such as a benzene ring, and R 55 To R 57 The compound of Formula 5-3 or Formula 5-4 may be one of the compounds 4-5 to 4-8 in Formula 6.

[0126] The light-emitting compound of the present disclosure may be one of the compounds in Formula 6.

[0127] [Molecular formula 6]

[0128]

[0129]

[0130] The light-emitting compounds in Formulas 1 to 6 provide blue light emission and are used for the EML 240 in the OLED D. Therefore, the lifespan of the OLED D and the organic light-emitting device 100 is greatly increased.

[0131] [Synthesis of the subject]

[0132] 1. Synthesis of Compound 1-1

[0133] (1) Compound I1-1c

[0134] [Reaction formula 1-1]

[0135]

[0136] In a 500 mL reactor, 8.5 g (50 mmol) of compound I1-1a, 18.6 g (50 mmol) of compound I1-1b, 0.45 g (2 mmol) of palladium acetate, 18.9 g (196 mmol) of sodium tert-butoxide, 0.8 g (4 mmol) of tri-tert-butylphosphine and 300 mL of toluene were added and stirred / refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 17.2 g of compound I1-1c. (yield 68%)

[0137] (2) Compound 1-1

[0138] [Reaction 1-2]

[0139]

[0140] In a 500mL reactor, 6.3g (12.5mmol) of compound I1-1c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 1-1. (yield 21%)

[0141] 2. Synthesis of Compound 1-2

[0142] (1) Compound I1-2c

[0143] [Reaction formula 2-1]

[0144]

[0145] In a 500 mL reactor, 8.5 g (50 mmol) of compound I1-2a, 18.6 g (50 mmol) of compound I1-2b, 0.45 g (2 mmol) of palladium acetate, 18.9 g (196 mmol) of sodium tert-butoxide, 0.8 g (4 mmol) of tri-tert-butylphosphine and 300 mL of toluene were added and stirred / refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 16.9 g of compound I1-2c. (yield 67%)

[0146] (2) Compound 1-2

[0147] [Reaction formula 2-2]

[0148]

[0149] In a 500mL reactor, 6.3g (12.5mmol) of compound I1-2c and 60mL of tert-butylbenzene were added to a 500mL reactor. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 19%)

[0150] 3. Synthesis of Compounds 1-4

[0151] (1) Compound I1-4c

[0152] [Reaction formula 3-1]

[0153]

[0154] In a 500 mL reactor, 8.5 g (50 mmol) of compound I1-4a, 19.4 g (50 mmol) of compound I1-4b, 0.45 g (2 mmol) of palladium acetate, 18.9 g (196 mmol) of sodium tert-butoxide, 0.8 g (4 mmol) of tri-tert-butylphosphine and 300 mL of toluene were added and stirred / refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 13.5 g of compound I1-4c. (yield 52%)

[0155] (2) Compound 1-4

[0156] [Reaction formula 3-2]

[0157]

[0158] In a 500mL reactor, 6.5g (12.5mmol) of compound I1-4c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 0.9g of compound 1-4. (yield 15%)

[0159] 4. Synthesis of Compounds 1-7

[0160] (1) Compound I1-7c

[0161] [Reaction 4-1]

[0162]

[0163] In a 500 mL reactor, 8.5 g (50 mmol) of compound I1-7a, 19.4 g (50 mmol) of compound I1-7b, 0.45 g (2 mmol) of palladium acetate, 18.9 g (196 mmol) of sodium tert-butoxide, 0.8 g (4 mmol) of tri-tert-butylphosphine and 300 mL of toluene were added and stirred / refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 16.9 g of compound I1-7c. (yield 65%)

[0164] (2) Compound 1-7

[0165] [Reaction 4-2]

[0166]

[0167] In a 500mL reactor, 6.5g (12.5mmol) of compound I1-7c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 1-7. (yield 20%)

[0168] 5. Synthesis of Compounds 1-8

[0169] (1) Compound I1-8c

[0170] [Reaction formula 5-1]

[0171]

[0172] In a 500 mL reactor, 8.5 g (50 mmol) of compound I1-8a, 18.6 g (50 mmol) of compound I1-8b, 0.45 g (2 mmol) of palladium acetate, 18.9 g (196 mmol) of sodium tert-butoxide, 0.8 g (4 mmol) of tri-tert-butylphosphine and 300 mL of toluene were added and stirred / refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 16.7 g of compound I1-8c. (Yield 66%)

[0173] (2) Compound 1-8

[0174] [Reaction formula 5-2]

[0175]

[0176] In a 500mL reactor, 6.3g (12.5mmol) of compound I1-8c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 1-8. (yield 18%)

[0177] 6. Synthesis of Compounds 1-9

[0178] (1) Compound I1-9c

[0179] [Reaction formula 6-1]

[0180]

[0181] In a 500 mL reactor, 8.5 g (50 mmol) of compound I1-9a, 19.4 g (50 mmol) of compound I1-9b, 0.45 g (2 mmol) of palladium acetate, 18.9 g (196 mmol) of sodium tert-butoxide, 0.8 g (4 mmol) of tri-tert-butylphosphine and 300 mL of toluene were added, and refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 18.5 g of compound I1-9c. (Yield 71%)

[0182] (2) Compound 1-9

[0183] [Reaction formula 6-2]

[0184]

[0185] In a 500mL reactor, 6.5g (12.5mmol) of compound I1-9c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 1-9. (yield 23%)

[0186] 7. Synthesis of Compound 2-1

[0187] (1) Compound I2-1c

[0188] [Reaction formula 7-1]

[0189]

[0190] In a 500mL reactor, 8.5g (50mmol) of compound I2-1a, 21.1g (50mmol) of compound I2-1b, 0.45g (2mmol) of palladium acetate, 18.9g (196mmol) of sodium tert-butoxide, 0.8g (4mmol) of tri-tert-butylphosphine and 300mL of toluene were added, and refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 17.7g of compound I2-1c. (Yield 64%)

[0191] (2) Compound 2-1

[0192] [Reaction 7-2]

[0193]

[0194] In a 500mL reactor, 6.9g (12.5mmol) of compound I2-1c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyllithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 2-1. (yield 18%)

[0195] 8. Synthesis of Compound 2-2

[0196] (1) Compound I2-2c

[0197] [Reaction formula 8-1]

[0198]

[0199] In a 500mL reactor, 8.5g (50mmol) of compound I2-2a, 21.1g (50mmol) of compound I2-2b, 0.45g (2mmol) of palladium acetate, 18.9g (196mmol) of sodium tert-butoxide, 0.8g (4mmol) of tri-tert-butylphosphine and 300mL of toluene were added, and refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 18.0g of compound I2-2c. (Yield 65%)

[0200] (2) Compound 2-2

[0201] [Reaction formula 8-2]

[0202]

[0203] In a 500mL reactor, 6.9g (12.5mmol) of compound I2-2c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 2-2. (yield 16%)

[0204] 9. Synthesis of Compound 2-3

[0205] (1) Compound I2-3c

[0206] [Reaction formula 9-1]

[0207]

[0208] In a 500mL reactor, 8.5g (50mmol) of compound I2-3a, 21.1g (50mmol) of compound I2-3b, 0.45g (2mmol) of palladium acetate, 18.9g (196mmol) of sodium tert-butoxide, 0.8g (4mmol) of tri-tert-butylphosphine and 300mL of toluene were added, and refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 18.3g of compound I2-3c. (Yield 66%)

[0209] (2) Compound 2-3

[0210] [Reaction formula 9-2]

[0211]

[0212] In a 500mL reactor, 6.9g (12.5mmol) of compound I2-3c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 2-3. (yield 19%)

[0213] 10. Synthesis of Compound 2-4

[0214] (1) Compound I2-4c

[0215] [Reaction formula 10-1]

[0216]

[0217] In a 500mL reactor, 8.5g (50mmol) of compound I2-4a, 21.9g (50mmol) of compound I2-4b, 0.45g (2mmol) of palladium acetate, 18.9g (196mmol) of sodium tert-butoxide, 0.8g (4mmol) of tri-tert-butylphosphine and 300mL of toluene were added, and refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 18.5g of compound I2-4c. (Yield 65%)

[0218] (2) Compound 2-4

[0219] [Reaction formula 10-2]

[0220]

[0221] In a 500mL reactor, 7.1g (12.5mmol) of compound I2-4c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 2-4. (yield 20%)

[0222] 11. Synthesis of Compound 2-6

[0223] (1) Compound I2-6c

[0224] [Reaction formula 11-1]

[0225]

[0226] In a 500mL reactor, 8.5g (50mmol) of compound I2-6a, 21.9g (50mmol) of compound I2-6b, 0.45g (2mmol) of palladium acetate, 18.9g (196mmol) of sodium tert-butoxide, 0.8g (4mmol) of tri-tert-butylphosphine and 300mL of toluene were added, and refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 18.5g of compound I2-6c. (Yield 65%)

[0227] (2) Compound 2-6

[0228] [Reaction formula 11-2]

[0229]

[0230] In a 500mL reactor, 7.1g (12.5mmol) of compound I2-6c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 2-6. (yield 24%)

[0231] 12. Synthesis of Compound 3-1

[0232] (1) Compound I3-1c

[0233] [Reaction formula 12-1]

[0234]

[0235] In a 500mL reactor, 8.5g (50mmol) of compound I3-1a, 21.1g (50mmol) of compound I3-1b, 0.45g (2mmol) of palladium acetate, 18.9g (196mmol) of sodium tert-butoxide, 0.8g (4mmol) of tri-tert-butylphosphine and 300mL of toluene were added, and refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 17.5g of compound I3-1c. (Yield 63%)

[0236] (2) Compound 3-1

[0237] [Reaction 12-2]

[0238]

[0239] In a 500mL reactor, 6.9g (12.5mmol) of compound I3-1c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 3-1. (yield 21%)

[0240] 13. Synthesis of Compound 3-4

[0241] (1) Compound I3-4c

[0242] [Reaction formula 13-1]

[0243]

[0244] In a 500mL reactor, 8.5g (50mmol) of compound I3-4a, 21.1g (50mmol) of compound I3-4b, 0.45g (2mmol) of palladium acetate, 18.9g (196mmol) of sodium tert-butoxide, 0.8g (4mmol) of tri-tert-butylphosphine and 300mL of toluene were added, and refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 18.6g of compound I3-4c. (Yield 67%)

[0245] (2) Compound 3-4

[0246] [Reaction 13-2]

[0247]

[0248] In a 500mL reactor, 6.9g (12.5mmol) of compound I3-4c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 3-4. (yield 19%)

[0249] 14. Synthesis of Compound 3-7

[0250] (1) Compound I3-7c

[0251] [Reaction 14-1]

[0252]

[0253] In a 500mL reactor, 8.5g (50mmol) of compound I3-7a, 21.1g (50mmol) of compound I3-7b, 0.45g (2mmol) of palladium acetate, 18.9g (196mmol) of sodium tert-butoxide, 0.8g (4mmol) of tri-tert-butylphosphine and 300mL of toluene were added, and refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 17.8g of compound I3-7c. (Yield 64%)

[0254] (2) Compound 3-7

[0255] [Reaction 14-2]

[0256]

[0257] In a 500mL reactor, 6.9g (12.5mmol) of compound I3-7c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 3-7. (yield 21%)

[0258] 15. Synthesis of Compound 3-8

[0259] (1) Compound I3-8c

[0260] [Reaction 15-1]

[0261]

[0262] In a 500mL reactor, 8.5g (50mmol) of compound I3-8a, 21.1g (50mmol) of compound I3-8b, 0.45g (2mmol) of palladium acetate, 18.9g (196mmol) of sodium tert-butoxide, 0.8g (4mmol) of tri-tert-butylphosphine and 300mL of toluene were added, and refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 18.3g of compound I3-8c. (Yield 66%)

[0263] (2) Compound 3-8

[0264] [Reaction 15-2]

[0265]

[0266] In a 500mL reactor, 6.9g (12.5mmol) of compound I3-8c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 3-8. (yield 20%)

[0267] 16. Synthesis of Compound 3-9

[0268] (1) Compound I3-9c

[0269] [Reaction 16-1]

[0270]

[0271] In a 500mL reactor, 8.5g (50mmol) of compound I3-9a, 21.1g (50mmol) of compound I3-9b, 0.45g (2mmol) of palladium acetate, 18.9g (196mmol) of sodium tert-butoxide, 0.8g (4mmol) of tri-tert-butylphosphine and 300mL of toluene were added, and refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 19.1g of compound I3-9c. (Yield 69%)

[0272] (2) Compound 3-9

[0273] [Reaction 16-2]

[0274]

[0275] In a 500mL reactor, 6.9g (12.5mmol) of compound I3-9c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 3-9. (yield 17%)

[0276] 17. Synthesis of Compound 4-1

[0277] (1) Compound I4-1c

[0278] [Reaction 17-1]

[0279]

[0280] In a 500mL reactor, 8.5g (50mmol) of compound I4-1a, 23.6g (50mmol) of compound I4-1b, 0.45g (2mmol) of palladium acetate, 18.9g (196mmol) of sodium tert-butoxide, 0.8g (4mmol) of tri-tert-butylphosphine and 300mL of toluene were added, and refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 17.8g of compound I4-1c. (yield 59%)

[0281] (2) Compound 4-1

[0282] [Reaction 17-2]

[0283]

[0284] In a 500mL reactor, 7.6g (12.5mmol) of compound I4-1c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 4-1. (yield 19%)

[0285] 18. Synthesis of Compound 4-3

[0286] (1) Compound I4-3c

[0287] [Reaction 18-1]

[0288]

[0289] In a 500mL reactor, 8.5g (50mmol) of compound I4-3a, 23.6g (50mmol) of compound I4-3b, 0.45g (2mmol) of palladium acetate, 18.9g (196mmol) of sodium tert-butoxide, 0.8g (4mmol) of tri-tert-butylphosphine and 300mL of toluene were added, and refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 20.5g of compound I4-3c. (Yield 68%)

[0290] (2) Compound 4-3

[0291] [Reaction 18-2]

[0292]

[0293] In a 500mL reactor, 7.6g (12.5mmol) of compound I4-3c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 4-3. (yield 22%)

[0294] 19. Synthesis of Compound 4-4

[0295] (1) Compound I4-4c

[0296] [Reaction 19-1]

[0297]

[0298] In a 500mL reactor, 8.5g (50mmol) of compound I4-4a, 23.6g (50mmol) of compound I4-4b, 0.45g (2mmol) of palladium acetate, 18.9g (196mmol) of sodium tert-butoxide, 0.8g (4mmol) of tri-tert-butylphosphine and 300mL of toluene were added, and refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 20.8g of compound I4-4c. (Yield 69%)

[0299] (2) Compound 4-4

[0300] [Reaction 19-2]

[0301]

[0302] In a 500mL reactor, 7.6g (12.5mmol) of compound I4-4c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 4-4. (yield 19%)

[0303] 20. Synthesis of Compounds 4-7

[0304] (1) Compound I4-7c

[0305] [Reaction formula 20-1]

[0306]

[0307] In a 500mL reactor, 35.9g (110mmol) of compound I4-7a, 9.1g (50mmol) of compound I4-7b, 0.45g (2mmol) of palladium acetate, 18.9g (196mmol) of sodium tert-butoxide, 0.8g (4mmol) of tri-tert-butylphosphine and 300mL of toluene were added and refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 26.6g of compound I4-7c. (Yield 70%)

[0308] (2) Compound 4-7

[0309] [Reaction 20-2]

[0310]

[0311] In a 500mL reactor, 9.5g (12.5mmol) of compound I4-7c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 4-7. (yield 16%)

[0312] 21. Synthesis of Compounds 4-8

[0313] (1) Compound I4-8c

[0314] [Reaction 21-1]

[0315]

[0316] In a 500mL reactor, 35.9g (110mmol) of compound I4-8a, 9.1g (50mmol) of compound I4-8b, 0.45g (2mmol) of palladium acetate, 18.9g (196mmol) of sodium tert-butoxide, 0.8g (4mmol) of tri-tert-butylphosphine and 300mL of toluene were added and refluxed for 5 hours. After the reaction was completed, the resultant was filtered and concentrated. The mixture was separated by column chromatography to obtain 25.9g of compound I4-8c. (Yield 68%)

[0317] (2) Compound 4-8

[0318] [Reaction 21-2]

[0319]

[0320] In a 500mL reactor, 9.5g (12.5mmol) of compound I4-8c and 60mL of tert-butylbenzene were added. 45mL (37.5mmol) of n-butyl lithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60°C for 3 hours. Then, nitrogen was blown in at 60°C to remove heptane. 6.3g (25mmol) of boron tribromide was added dropwise at -78°C. After dropwise 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 dropwise 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 4-8. (yield 15%)

[0321] In the EML 240 , the first compound 242 serves as a dopant (emitter) emitting blue light.

[0322] In addition, the EML 240 may further include a second compound 244 as a main body. In this case, in the EML 240, the first compound 242 may have about 0.1 to 30 weight percent, preferably about 0.1 to 10 weight percent, and more preferably about 1 to 5 weight percent. The EML 240 may have about to The thickness is preferably about to The thickness is preferably about to Thickness.

[0323] The second compound 244 as a host may be an anthracene derivative. For example, the second compound 244 may be represented by Formula 7.

[0324] [Molecular Formula 7]

[0325]

[0326] In Formula 7, 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. In this case, the hydrogen in the anthracene derivative is not deuterated or is partially or fully deuterated. That is, there is no hydrogen in the anthracene derivative or a part or all of the hydrogen is replaced by deuterium.

[0327] In Formula 7, 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.

[0328] 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.

[0329] In Formula 7, 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.

[0330] The second compound 244 in Formula 7 may be one of the compounds in Formula 8.

[0331] [Molecular formula 8]

[0332]

[0333] The HIL 210 may include a plurality of amines selected from the group consisting of 4,4',4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4"-tris(N,N-diphenylamino)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-nitropropene. ,4″-diamine (NPB or NPD), 1,4,5,8,9,11-hexaazabenzohexacarbonitrile (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 at least one compound. Alternatively, the HIL 210 may include the compound of Formula 15 as a host and the compound of Formula 16 as a dopant.

[0334] The HTL 220 may include a material selected from 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] (polyTPD), (poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))] (TFPD), B), di-[4-(N,N-di-p-tolylamino)-phenyl]cyclohexane (TAPC), 3,5-di(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, the HTL 220 may include the compound of Formula 15.

[0335] The EBL 230 disposed between the HTL 220 and the EML 240 is formed to prevent electrons from heading toward the HTL 220. The EBL 230 includes an electron blocking material of an amine derivative. The electron blocking material is represented by Formula 9.

[0336] [Molecular formula 9]

[0337]

[0338] In Formula 9, L is a C6 to C30 arylene group, and a is 0 or 1. R1 and R2 are each independently selected from a C6 to C30 aryl group and a C5 to C30 heteroaryl group.

[0339] For example, L may be a phenylene group, and R1 and R2 may each be selected from a biphenyl group, a fluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a carbazolylphenyl group, a dibenzothienyl group, and a dibenzofuranyl group.

[0340] That is, the electron blocking material may be an amine derivative substituted with spirofluorene (eg, “spirofluorene-substituted amine derivative”).

[0341] The electron blocking material of Formula 9 may be one of the following Formula 10:

[0342] [Molecular Formula 10]

[0343]

[0344]

[0345] The HBL 250 disposed between the EML 240 and the EIL 260 is formed to prevent holes from heading 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 11.

[0346] [Molecular Formula 11]

[0347]

[0348] In Formula 11, Y1 to Y5 are each independently CR1 or N, and one to three of Y1 to Y5 are N. R1 is independently a C6 to C30 aryl group. L is a C6 to C30 arylene group, and R2 is a C6 to C30 aryl group or a C5 to C30 heteroaryl group. R3 is hydrogen, or two adjacent R3s form a condensed ring. "a" is 0 or 1, "b" is 1 or 2, and "c" is an integer from 0 to 4.

[0349] The hole blocking material of Formula 11 may be one of Formula 12 below.

[0350] [Molecular Formula 12]

[0351]

[0352]

[0353]

[0354] Alternatively, the HBL 250 may include a benzimidazole derivative as a hole blocking material. For example, the benzimidazole derivative as a hole blocking material is represented by Formula 13.

[0355] [Molecular Formula 13]

[0356]

[0357] In formula 13, 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 30 Aryl.

[0358] For example, Ar may be naphthalene or anthracene, R1 may be benzimidazole or phenyl, and R2 may be methyl, ethyl or phenyl.

[0359] The hole blocking material of Formula 13 may be one of Formula 14 below.

[0360] [Molecular Formula 14]

[0361]

[0362] The HBL 250 may include at least one of the hole blocking material of Formula 11 and the hole blocking material of Formula 13.

[0363] 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 EML 240 may have a thickness of about to Each of the EBL 230 and the HBL 250 may have a thickness of about to and the HTL 220 may have a thickness of about to The EBL 230 and the HBL 250 may have the same thickness.

[0364] The HBL 250 may include the compound of Formula 11 and the compound of Formula 13. For example, in the HBL 250, the compound of Formula 11 and the compound of Formula 13 may have the same weight percentage.

[0365] In this case, the thickness of the EML 240 may be greater than the thickness of the EBL 250, 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 EML 240 may have a thickness of about to The thickness of the EBL can be about to The HBL 250 may have a thickness of about to and the HTL 220 may have a thickness of about to Thickness.

[0366] The electron blocking material in Formula 11 and / or Formula 13 has excellent hole blocking properties and excellent electron transport properties. Therefore, an electron transport layer may be provided, and the HBL 250 may directly contact the HIL 260 or the second electrode 164 .

[0367] The EIL 260 may include at least one of an alkali metal (e.g., Li), an alkali halide compound (e.g., LiF, CsF, NaF, or BaF2), and an organic metal compound (e.g., Liq, lithium benzoate, or sodium stearate), but is not limited thereto. Alternatively, the EIL 260 may include the compound of Formula 17 (as a host) and an alkali metal (as a dopant).

[0368] In the OLED D, the EML 240 includes the light-emitting compound 242 of Formula 1, thereby significantly improving the lifespan of the OLED D and the organic light-emitting display device 100 .

[0369] [Organic Light Emitting Diode]

[0370] Anode (ITO, 0.5 mm), HIL (Formula 15 (97 wt%) and Formula 16 (3 wt%) were deposited in sequence. )、HTL(Molecular formula 15, ), EBL (compound EBL-11 in formula 10, ), EML (compound H-1 in formula 8 (host, 98 wt%) and dopant (2 wt%), ), HBL (compound E1 in formula 12, )、EIL(Molecular Formula 17(98wt%) and Li(2wt%), ) and cathode (Al, ). An encapsulation film is formed by using a UV curable epoxy resin and a moisture absorbent to form an OLED.

[0371] [Molecular Formula 15]

[0372]

[0373] [Molecular Formula 16]

[0374]

[0375] [Molecular Formula 17]

[0376]

[0377] (1) Comparative Example 1 and Comparative Example 2 (Ref1 and Ref2)

[0378] The compound “Ref-1” in Formula 18 and the compound “Ref-2” in Formula 19 are respectively used as dopants to form the EML.

[0379] (2) Example 1 to Example 21 (Ex1 to Ex21)

[0380] Compounds 1-1, 1-2, 1-4, 1-7 to 1-9, 2-1 to 2-4, 2-6, 3-1, 3-4, 3-7 to 3-9, 4-1, 4-3, 4-4, 4-7, and 4-9 in Formula 6 are respectively used as dopants to form the EML.

[0381] [Molecular Formula 18]

[0382]

[0383] [Molecular formula 19]

[0384]

[0385] The characteristics of the OLEDs manufactured in Comparative Examples 1 and 2 and Examples 1 to 21, namely, voltage (V), external quantum efficiency (EQE), color coordinates (CIE) and lifetime (T95) were measured and listed in Tables 1 and 2. The characteristics of the OLEDs were measured using a current source (KEITHLEY) and a photometer (PR650) at room temperature. At 10 mA / cm 2 The driving voltage, external quantum efficiency and color coordinates were measured at a current density of 22.5 mA / cm 2 conditions to achieve 95% of the lifespan.

[0386] Table 1

[0387] Dopant V EQE(%) CIE(x,y) <![CDATA[T 95 (hr)]]> Ref1 Ref-1 3.95 6.31 (0.140,0.060) 76 Ref2 Ref-2 3.94 6.28 (0.140,0.075) 72 Ex1 1-1 3.93 6.42 (0.141,0.128) 115 Ex2 1-2 3.94 6.25 (0.140,0.121) 109 Ex3 1-4 3.91 6.21 (0.140,0.120) 114 Ex4 1-7 3.91 6.35 (0.140,0.123) 120 Ex5 1-8 3.90 5.99 (0.141,0.120) 115 Ex6 1-9 3.97 6.08 (0.140,0.119) 103 Ex7 2-1 3.95 6.15 (0.140,0.078) 105 Ex8 2-2 3.96 6.32 (0.140,0.186) 111 Ex9 2-3 3.92 6.75 (0.141,0.129) 117 Ex10 2-4 3.88 6.66 (0.140,0.079) 101 Ex11 2-6 3.90 6.49 (0.142,0.125) 105

[0388] Table 2

[0389] Dopant V EQE(%) CIE(x,y) <![CDATA[T 95 (hr)]]> Ex12 3-1 3.99 6.38 (0.141,0.071) 110 Ex13 3-4 3.98 6.47 (0.140,0.178) 106 Ex14 3-7 3.96 5.72 (0.140,0.046) 108 Ex15 3-8 3.98 5.44 (0.141,0.045) 102 Ex16 3-9 4.01 5.51 (0.140,0.046) 99 Ex17 4-1 3.88 6.28 (0.140,0.055) 111 Ex18 4-3 3.89 6.29 (0.140,0.087) 114 Ex19 4-4 3.92 6.45 (0.141,0.115) 109 Ex20 4-7 3.91 6.50 (0.140,0.095) 102 Ex21 4-8 3.91 6.42 (0.140,0.127) 118

[0390] As shown in Tables 1 and 2, the lifespans of the OLEDs in Ex1 to Ex21 using the light-emitting compound of the present disclosure as a dopant are significantly improved compared to the OLEDs of Ref1 and Ref2.

[0391] In particular, as can be seen from Examples 1, 3 to 5 and 12 to 14, when compounds 1-1, 1-4, 1-7, 1-8, 3-1, 3-4 and 3-7 (in which the carbon atom adjacent to the nitrogen atom is substituted with a D-substituted alkyl group (e.g., CD3)) are used as dopants, the lifespan of the OLED is further increased.

[0392] In addition, as can be seen from Examples 8, 9 and 11, when compounds 2-2, 2-3 and 2-6 (in which the carbon atom adjacent to the heteroatom in the five-membered ring is substituted with a D-substituted alkyl group (e.g., CD3)) are used as dopants, the lifetime of the OLED is further increased.

[0393] Figure 4is a schematic cross-sectional view showing an OLED having a series structure of two light emitting units of an organic light emitting display device according to a first embodiment of the present disclosure.

[0394] 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 having a first EML 320, a second light emitting portion 330 having 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 located in the blue pixel.

[0395] 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.

[0396] The CGL 350 is located 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 located between the first electrode 160 and the CGL 350, and the second light emitting portion 320 is located between the second electrode 160 and the CGL 350.

[0397] 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.

[0398] 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 .

[0399] 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 6.

[0400] The EML 320 may further include a second compound 324. For example, the second compound 324 may be represented by Formula 7 and may be one of the compounds in Formula 8.

[0401] In the first EML 320, the first compound 322 has a weight percentage less than the second compound 324. The first compound 322 may be used as a dopant (emitter), and the second compound 324 may be used as a host. For example, in the first EML 320, the first compound 322 may have a weight percentage of about 0.1 to 30. In order to provide sufficient luminous efficiency and lifespan, the weight percentage of the first compound 322 may be about 0.1 to 10, preferably about 1 to 5.

[0402] The first EBL 316 may include the compound of Formula 9 as an electron blocking material. In addition, the first HBL 318 may include at least one of the compounds of Formula 11 and Formula 13 as a hole blocking material.

[0403] 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.

[0404] 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 .

[0405] The second EML 340 includes the light emitting compound of 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 of Formula 6.

[0406] The second EML 340 may further include a fourth compound 344. For example, the fourth compound 344 may be represented by Formula 7 and may be one of the compounds in Formula 8.

[0407] In the second EML 340, the third compound 342 may have a weight percentage less than that of the fourth compound 344. In the second EML 340, the third compound 342 may be used as a dopant (emitter), and the fourth compound 344 may be used as a host. For example, in the second EML 340, the third compound 342 has a weight percentage of about 0.1 to 30. In order to provide sufficient luminous efficiency and lifespan, the weight percentage of the third compound 342 may be about 0.1 to 10, preferably about 1 to 5.

[0408] 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 percentage of the first compound 322 in the first EML 320 and the weight percentage of the third compound 342 in the second EML 340 may be the same or different.

[0409] The second EBL 334 may include the electron blocking material of Formula 9. In addition, the second HBL 336 may include at least one of the hole blocking material of Formula 11 and the hole blocking material of Formula 13.

[0410] The CGL 350 is located 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.

[0411] The N-type CGL 352 is located between the first HBL 318 and the second HTL 332 , and the P-type CGL 354 is located between the N-type CGL 352 and the second HTL 332 .

[0412] In the OLED D, since each of the first EML 320 and the second EML 340 includes the light-emitting compound of Formula 1 as the first compound 322 and the third compound 342 , respectively, the light-emitting efficiency and lifespan of the OLED D and the organic light-emitting display device 100 are improved.

[0413] In addition, since the first light emitting portion 310 and the second light emitting portion for emitting blue light are stacked, the organic light emitting display device 100 provides an image having a high color temperature.

[0414] Figure 5 is a schematic cross-sectional view showing an organic light emitting display device according to a second embodiment of the present disclosure. Figure 6 2 is a schematic cross-sectional view showing an OLED having a tandem structure of two light emitting parts of 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 series structure of three light-emitting portions of an organic light-emitting display device according to a second embodiment of the present disclosure.

[0415] like Figure 5As shown, the organic light emitting display device 400 includes: a first substrate 410, in which red pixels RP, green pixels GP and blue pixels BP are defined; a second substrate 470, facing the first substrate 410; an OLED D, located between the first substrate 410 and the second substrate 470 and providing white light emission; and a color filter layer 480, located between the OLED D and the second substrate 470.

[0416] Each of the first substrate 410 and the second substrate 470 may be a glass substrate or a flexible substrate. For example, each of the first substrate 410 and the second substrate 470 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.

[0417] The buffer layer 420 is formed on the substrate, and the TFT Tr corresponding to each of the red pixel RP, the green pixel GP, and the blue pixel BP is formed on the buffer layer 420. The buffer layer 420 may be omitted.

[0418] The semiconductor layer 422 is formed on the buffer layer 420. The semiconductor layer 422 may include an oxide semiconductor material or polysilicon.

[0419] The 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.

[0420] The gate 430 formed of a conductive material (eg, metal) is formed on the gate insulating layer 424 to correspond to the center of the semiconductor layer 422 .

[0421] An interlayer insulating layer 432 formed of an insulating material is formed on the gate electrode 430. The interlayer insulating layer 432 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride, or an organic material such as benzocyclobutene or photo acrylic.

[0422] The interlayer insulating layer 432 includes a first contact hole 434 and a second contact hole 436 exposing both sides of the semiconductor layer 422. The first contact hole 434 and the second contact hole 436 are located at both sides of the gate 430 to be spaced apart from the gate 430.

[0423] A source electrode 440 and a drain electrode 442 formed of a conductive material (eg, metal) are formed on the interlayer insulating layer 432 .

[0424] 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.

[0425] 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.

[0426] 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.

[0427] In addition, a power supply line which may be formed parallel to and spaced apart from one of the gate line and the data line and a storage capacitor for maintaining a voltage of the gate electrode of the TFT Tr in one frame may be further formed.

[0428] The passivation layer 450 is formed to cover the TFT Tr, and the passivation layer 450 includes a drain contact hole 452 exposing the drain electrode 442 of the TFT Tr.

[0429] The first electrode 460 connected to the drain electrode 442 of the TFT Tr through the drain contact hole 452 is 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 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).

[0430] 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 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 460 may have a three-layer structure of ITO / Ag / ITO or ITO / APC / ITO.

[0431] The bank layer 466 is formed on the passivation layer 450 to cover the edge of the first electrode 460. That is, in the pixel, the bank layer 466 is located at the boundary of the pixel and exposes the center of the first electrode 460. 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 162 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.

[0432] The organic light emitting layer 462 is formed on the first electrode 460 .

[0433] refer to 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.

[0434] 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.

[0435] The CGL 750 is located between the first light emitting portion 710 and the second light emitting portion 730, and the first light emitting portion 710, the CGL 750 and the second light emitting portion 730 are sequentially stacked on the first electrode 460. That is, the first light emitting portion 710 is located between the first electrode 460 and the CGL 750, and the second light emitting portion 720 is located between the second electrode 460 and the CGL 750.

[0436] 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.

[0437] 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 .

[0438] The first EML 720 includes the light emitting compound in Formula 1 as the first compound 722 and provides blue light emission. For example, the first compound 722 in the first EML 720 may be one of the compounds in Formula 6.

[0439] The EML 720 may further include a second compound 724. For example, the second compound 724 may be represented by Formula 7 and may be one of the compounds in Formula 8.

[0440] In the first EML 720, the first compound 722 has a weight percentage less than the second compound 724. The first compound 722 may be used as a dopant (emitter), and the second compound 724 may be used as a host. For example, in the first EML 720, the first compound 722 may have a weight percentage of about 0.1 to 30. In order to provide sufficient luminous efficiency and lifespan, the weight percentage of the first compound 722 may be about 0.1 to 10, preferably about 1 to 5.

[0441] The first EBL 716 may include the compound of Formula 9 as an electron blocking material. In addition, the first HBL 718 may include at least one of the compounds of Formula 11 and Formula 13 as a hole blocking material.

[0442] 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.

[0443] 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 .

[0444] 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.

[0445] In the second EML 740, the host 745 may have about 70 to 99.9 weight percent, and the yellow-green dopant 743 may have about 0.1 to 30 weight percent. To provide sufficient light emitting efficiency, the yellow-green dopant 744 may have about 0.1 to 10 weight percent, preferably about 1 to 5 weight percent.

[0446] The second EBL 734 may include the compound of Formula 9 as an electron blocking material. In addition, the second HBL 736 may include at least one of the compounds of Formula 11 and Formula 13 as a hole blocking material.

[0447] The CGL 750 is located 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.

[0448] The N-type CGL 752 is located between the first HBL 718 and the second HTL 732 , and the P-type CGL 754 is located between the N-type CGL 752 and the second HTL 732 .

[0449] exist Figure 6 , the first EML 720 between the first electrode 460 and the CGL 750 includes the first compound 722 as the light-emitting compound of the present disclosure and the second compound 724 as the anthracene derivative, and the second EML 740 between the second electrode 464 and the CGL 750 is a yellow-green EML. Alternatively, the first EML 720 between the first electrode 460 and the CGL 750 may be a yellow-green EML, and the second EML 740 between the second electrode 464 and the CGL 750 may include the light-emitting compound of the present disclosure and the anthracene derivative and be a blue EML.

[0450] In the OLED D, since the first EML 720 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.

[0451] 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.

[0452] refer to Figure 7 The organic light-emitting layer 462 includes: a first light-emitting portion 530, including a first EML 520; a second light-emitting portion 550, including a second EML 540; a third light-emitting portion 570, including a third EML 560; a first CGL 580, located between the first light-emitting portion 530 and the second light-emitting portion 550; and a second CGL 590, located between the second light-emitting portion 550 and the third light-emitting portion 570.

[0453] The first CGL 580 is located between the first light emitting portion 530 and the second light emitting portion 550, and the second CGL 590 is located 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 located between the first electrode 460 and the first CGL 570, the second light emitting portion 550 is located between the first CGL 580 and the second CGL 590, and the third light emitting portion 570 is located between the second electrode 460 and the second CGL 590.

[0454] 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 HTL 532, the first HTL 534, and the first EBL 536 are located between the first electrode 460 and the first EML 520, and the first HBL 538 is located between the first EML 520 and the first CGL 580.

[0455] The first EML 520 includes the light emitting compound of 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 of Formula 6.

[0456] The EML 520 may further include a second compound 524. For example, the second compound 524 may be represented by Formula 7 and may be one of the compounds in Formula 8.

[0457] In the first EML 520, the first compound 522 has a weight percentage less than the second compound 524. The first compound 522 may be used as a dopant (emitter), and the second compound 524 may be used as a host. For example, in the first EML 520, the weight percentage of the first compound 522 may be about 0.1 to 30. In order to provide sufficient luminous efficiency and lifespan, the weight percentage of the first compound 522 may be about 0.1 to 10, preferably about 1 to 5.

[0458] The first EBL 536 may include the compound of Formula 9 as an electron blocking material. In addition, the first HBL 538 may include at least one compound of Formula 11 and Formula 13 as a hole blocking material.

[0459] The second EML 550 may include a second HTL 552, a second EML 540, and an electron transport layer (ETL) 554. The second HTL 552 is located between the first CGL 580 and the second EML 540, and the ETL 554 is located between the second EML 540 and the second CGL 590.

[0460] 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.

[0461] 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 in which a lower layer includes a host and a red dopant (or a green dopant) and an upper layer includes a host and a green dopant (or a red dopant).

[0462] The second EML 540 may have a three-layer structure in which a first layer includes a host and a red dopant, a second layer includes a host and a yellow-green dopant, and a third layer includes a host and a green dopant.

[0463] 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 .

[0464] 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 6.

[0465] The third EML 560 may further include a fourth compound 564. For example, the fourth compound 564 may be represented by Formula 7 and may be one of the compounds in Formula 8.

[0466] 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 be used as a dopant (emitter), and the fourth compound 564 may be used as a host. For example, in the third EML 560, the weight percentage of the third compound 562 is about 0.1 to 30. In order to provide sufficient luminous efficiency and lifespan, the weight percentage of the third compound 562 may be about 0.1 to 10, preferably about 1 to 5.

[0467] 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 percentage of the first compound 522 in the first EML 520 and the weight percentage of the third compound 562 in the third EML 560 may be the same or different.

[0468] The second EBL 574 may include the electron blocking material of Formula 9. In addition, the second HBL 576 may include at least one of the hole blocking material of Formula 11 and the hole blocking material of Formula 13.

[0469] The first CGL 580 is located between the first light emitting portion 530 and the second light emitting portion 550, and the second CGL 590 is located between the second light emitting portion 550 and the third light emitting portion 570. That is, the first light emitting stack 530 and the second light emitting stack 550 are connected through the first CGL 580, and the second light emitting stack 550 and the third light emitting stack 570 are connected through the second CGL 590. The first CGL 580 may be a PN junction CGL of the first N-type CGL 582 and the first P-type CGL 584, and the second CGL 590 may be a PN junction CGL of the second N-type CGL 592 and the second P-type CGL 594.

[0470] In the first CGL 580 , a first N-type CGL 582 is located between the first HBL 538 and the second HTL 552 , and a first P-type CGL 584 is located between the first N-type CGL 582 and the second HTL 552 .

[0471] In the second CGL 590 , the second N-type CGL 592 is located between the ETL 554 and the third HTL 572 , and the second P-type CGL 594 is located between the second N-type CGL 592 and the third HTL 572 .

[0472] In the OLED D, since each of the first EML 520 and the third EML 560 includes 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.

[0473] 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.

[0474] exist Figure 7 , the OLED D has a triple-stacked 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 an additional light emitting portion and a CGL.

[0475] Reference again Figure 5 , a second electrode 464 is formed above the substrate 410 on which the organic light emitting layer 462 is formed.

[0476] 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.

[0477] The first electrode 460 , the organic light emitting layer 462 , and the second electrode 464 constitute an OLED D.

[0478] The color filter layer 480 is located 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 482 may include at least one of a green dye and a green pigment, and the blue color filter 482 may include at least one of a blue dye and a blue pigment.

[0479] 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 formed directly on the OLED D.

[0480] 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, without being limited thereto. The encapsulation film may be omitted.

[0481] 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.

[0482] exist Figure 5 In the OLED D, the first electrode 460 and the second electrode 464 are a reflective electrode and a transparent (or semi-transparent) electrode, respectively, and the color filter layer 480 is disposed above the OLED D. Alternatively, when the first electrode 460 and the second electrode 464 are a transparent (or semi-transparent) electrode and a reflective electrode, respectively, the color filter layer 480 may be disposed between the OLED D and the first substrate 410.

[0483] A color conversion layer (not shown) may be formed between the OLED D and the color filter layer 480. The color conversion layer may include a red conversion layer, a green conversion layer, and a blue conversion layer corresponding to the red pixel RP, the green pixel GP, and the blue pixel BP, respectively. White light from the OLED D is converted into red light, green light, and blue light by the red conversion layer, the green conversion layer, and the blue 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.

[0484] A color conversion layer may be included instead of the color filter layer 480 .

[0485] 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 color filter 482, the green color filter 484, and the blue color filter 486. Therefore, red light, green light, and blue light are provided from the red pixel RP, the green pixel GP, and the blue pixel BP, respectively.

[0486] exist Figures 5 to 7 In the embodiment, the OLED D emitting white light is used for a display device. Alternatively, the OLED D may be formed on the entire surface of the substrate (without at least one of a driving element and a color filter layer) for a lighting device. 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.

[0487] Figure 8 is a schematic cross-sectional view showing an organic light emitting display device according to a third embodiment of the present disclosure.

[0488] like Figure 8 As shown, the organic light emitting display device 600 includes: a first substrate 610, in which red pixels BP, green pixels GP and blue pixels BP are defined; a second substrate 670, facing the first substrate 610; an OLED D, located between the first substrate 610 and the second substrate 670 and providing white light emission; and a color conversion layer 680, located between the OLED D and the second substrate 670.

[0489] Although not shown, a color filter may be formed between the second substrate 670 and each color conversion layer 680 .

[0490] Each of the first substrate 610 and the second substrate 670 may be a glass substrate or a flexible substrate. For example, each of the first substrate 410 and the second substrate 470 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.

[0491] A TFT Tr corresponding to each of the red pixel BP, 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 of the TFT Tr) is formed to cover the TFT Tr.

[0492] The OLED D including the first electrode 660, the organic light emitting layer 662, and the second electrode 664 is formed on the passivation layer 650. In this case, the first electrode 660 may be connected to the drain electrode of the TFT Tr through the drain contact hole 652.

[0493] The bank layer 666 is formed on the passivation layer 650 to cover the edge of the first electrode 660. That is, in the pixel, the bank layer 666 is located at the boundary of the pixel and exposes the center of the first electrode 460. Since the OLED D emits blue light in the red pixel BP, the green pixel GP, and the blue pixel BP, the organic light emitting layer 162 may be formed as a common layer in the red pixel BP, 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.

[0494] OLED D emits blue light and can have Figure 3 or Figure 4 That is, an OLED D is formed in each of a red pixel BP, a green pixel GP, and a blue pixel BP and provides blue light.

[0495] 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.

[0496] 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.

[0497] Therefore, the organic light emitting display device 600 can display a full-color image.

[0498] 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 .

[0499] It will be apparent to those skilled in the art that various modifications and variations may be made to the embodiments of the present disclosure without departing from the spirit or scope of the present disclosure. Therefore, it is intended that modifications and variations cover the present disclosure as long as they fall within the scope of the appended claims and their equivalents.

Claims

1. A light-emitting compound represented by one of the formula 2-2, the formula 3-2, the formulas 4-2 to 4-4, the formula 5-2 and the formula 5-4: [Molecular formula 2-2] in, In the molecular formula 2-2, one of Z1 to Z4 is N, three of Z1 to Z4 are CR4, wherein one of the three R4 is a C1 to C10 alkyl group substituted with deuterium, wherein the rest of the three R4 are independently selected from hydrogen, unsubstituted C1 to C10 alkyl, C6 to C30 arylamino unsubstituted or substituted by C1 to C10 alkyl, C6 to C30 aryl unsubstituted or substituted by C1 to C10 alkyl, and C5 to C30 heteroaryl unsubstituted or substituted by C1 to C10 alkyl, Among them, R 11 To R 17 are each independently selected from hydrogen, unsubstituted C1 to C10 alkyl, C6 to C30 arylamino unsubstituted or substituted by C1 to C10 alkyl, C6 to C30 aryl unsubstituted or substituted by C1 to C10 alkyl, and C5 to C30 heteroaryl unsubstituted or substituted by C1 to C10 alkyl, [Molecular formula 3-2] Wherein, in the molecular formula 3-2, two adjacent R4 are connected to each other to form a condensed ring, and one of the remaining two R4 is a C1 to C10 alkyl group substituted with deuterium, wherein the remaining one R4 is selected from hydrogen, unsubstituted C1 to C10 alkyl, C6 to C30 arylamino unsubstituted or substituted by C1 to C10 alkyl, C6 to C30 aryl unsubstituted or substituted by C1 to C10 alkyl, and C5 to C30 heteroaryl unsubstituted or substituted by C1 to C10 alkyl, Among them, R 21 To R 27 are each independently selected from hydrogen, unsubstituted C1 to C10 alkyl, C6 to C30 arylamino unsubstituted or substituted by C1 to C10 alkyl, C6 to C30 aryl unsubstituted or substituted by C1 to C10 alkyl, and C5 to C30 heteroaryl unsubstituted or substituted by C1 to C10 alkyl, [Molecular formula 4-2] [Molecular formula 4-3] [Molecular formula 4-4] Wherein, in the molecular formula 4-2 to the molecular formula 4-4, one of Z1 to Z4 is N, three of Z1 to Z4 are CR4, wherein one of the three R4 is a C1 to C10 alkyl group substituted with deuterium, wherein the rest of the three R4 are independently selected from hydrogen, deuterium, C1 to C10 alkyl which is unsubstituted or substituted by deuterium, C6 to C30 arylamino 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, or two adjacent R4 to R6 are connected to each other to form a condensed ring, Among them, R 31 To R 37 are each independently selected from hydrogen, unsubstituted C1 to C10 alkyl, C6 to C30 arylamino unsubstituted or substituted by C1 to C10 alkyl, C6 to C30 aryl unsubstituted or substituted by C1 to C10 alkyl, and C5 to C30 heteroaryl unsubstituted or substituted by C1 to C10 alkyl, [Molecular formula 5-2] Wherein, in the molecular formula 5-2, two adjacent ones of the four R4s or R5 and R6 are connected to form a condensed ring, and one of the remaining four of R4, R5 and R6 is a C1 to C10 alkyl group substituted with deuterium, wherein the rest of R4, R5 and R6 are independently selected from hydrogen, unsubstituted C1 to C10 alkyl, C6 to C30 arylamino unsubstituted or substituted by C1 to C10 alkyl, C6 to C30 aryl unsubstituted or substituted by C1 to C10 alkyl, and C5 to C30 heteroaryl unsubstituted or substituted by C1 to C10 alkyl, Among them, R 41 To R 47 are each independently selected from hydrogen, unsubstituted C1 to C10 alkyl, C6 to C30 arylamino unsubstituted or substituted by C1 to C10 alkyl, C6 to C30 aryl unsubstituted or substituted by C1 to C10 alkyl, and C5 to C30 heteroaryl unsubstituted or substituted by C1 to C10 alkyl, [Molecular formula 5-4] Wherein, in the molecular formula 5-4, Y5 is O or S, wherein two adjacent ones of the four R4s or R5 and R6 are connected to form a condensed ring, and one of the remaining four of R4, R5 and R6 is a C1 to C10 alkyl group substituted with deuterium, wherein the rest of R4, R5 and R6 are independently selected from hydrogen, unsubstituted C1 to C10 alkyl, C6 to C30 arylamino unsubstituted or substituted by C1 to C10 alkyl, C6 to C30 aryl unsubstituted or substituted by C1 to C10 alkyl, and C5 to C30 heteroaryl unsubstituted or substituted by C1 to C10 alkyl, Among them, R8, R9 and R 51 To R 54 One of the following is a deuterated C1 to C10 alkyl group, Among them, R8, R9 and R 51 To R 54 The rest are independently selected from hydrogen, unsubstituted C1 to C10 alkyl, C6 to C30 arylamino unsubstituted or substituted by C1 to C10 alkyl, C6 to C30 aryl unsubstituted or substituted by C1 to C10 alkyl, and C5 to C30 heteroaryl unsubstituted or substituted by C1 to C10 alkyl, or R 51 To R 54 Two adjacent R8 and R9 are connected to form a condensed ring, Among them, R 55 To R 57 are each independently selected from hydrogen, unsubstituted C1 to C10 alkyl, C6 to C30 arylamino unsubstituted or substituted by C1 to C10 alkyl, C6 to C30 aryl unsubstituted or substituted by C1 to C10 alkyl, and C5 to C30 heteroaryl unsubstituted or substituted by C1 to C10 alkyl, Wherein, in each of Formula 2-2, Formula 3-2, Formulas 4-2 to 4-4, Formula 5-2 and Formula 5-4, each R1 is independently selected from hydrogen, unsubstituted C1 to C10 alkyl, C6 to C30 arylamino unsubstituted or substituted by C1 to C10 alkyl, C6 to C30 aryl unsubstituted or substituted by C1 to C10 alkyl, and C5 to C30 heteroaryl unsubstituted or substituted by C1 to C10 alkyl, and Y3 is O or S.

2. The luminescent compound according to claim 1, wherein The molecular formulas 4-2 to 4-4 are respectively represented by molecular formulas 4-5 to 4-7: [Molecular formula 4-5] [Molecular formula 4-6] [Molecular formula 4-7] Wherein, in the molecular formulas 4-5 to 4-7, Y4 is O or S, wherein one of Z5 to Z8 is N, and the remaining three of Z5 to Z8 are CR7, wherein one of the three R7 is a C1 to C10 alkyl group substituted by deuterium, and the rest of the three R7 are independently selected from hydrogen, unsubstituted C1 to C10 alkyl, C6 to C30 arylamino unsubstituted or substituted by C1 to C10 alkyl, C6 to C30 aryl unsubstituted or substituted by C1 to C10 alkyl, and C5 to C30 heteroaryl unsubstituted or substituted by C1 to C10 alkyl, Among them, R 35 To R 37 Each is independently selected from hydrogen, unsubstituted C1 to C10 alkyl, C6 to C30 arylamino unsubstituted or substituted by C1 to C10 alkyl, C6 to C30 aryl unsubstituted or substituted by C1 to C10 alkyl, and C5 to C30 heteroaryl unsubstituted or substituted by C1 to C10 alkyl.

3. The luminescent compound according to claim 1, wherein The luminescent compound is a compound of formula 6: [Molecular formula 6] 4. An organic light-emitting device, comprising: substrate; and an organic light emitting diode located on the substrate and comprising a first electrode, a second electrode facing the first electrode, and a first light emitting material layer including a first compound and located between the first electrode and the second electrode, Wherein, the first compound is the light-emitting compound according to claim 1.

5. The organic light-emitting device according to claim 4, wherein: The first luminescent material layer further includes a second compound, Wherein, the second compound is represented by Molecular Formula 7: [Molecular Formula 7] 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, Therein, hydrogen is not deuterated or is partially or fully deuterated.

6. The organic light-emitting device according to claim 4, wherein: The organic light emitting diode further comprises: a second light-emitting material layer including a third compound and located between the first light-emitting material layer and the second electrode; and a first charge generation layer, the first charge generation layer being located between the first light emitting material layer and the second light emitting material layer, Wherein, the third compound is the light-emitting compound according to claim 1.

7. The organic light-emitting device according to claim 6, wherein: The organic light emitting diode further comprises: a third light emitting material layer, the third light emitting material layer being located between the first charge generation layer and the second light emitting material layer; and 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, The third luminescent material layer emits yellow-green light or red and green light.

8. The organic light-emitting device according to claim 4, wherein: The organic light emitting diode further comprises: a second light-emitting material layer, which emits yellow-green light and is located 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.

9. The organic light-emitting device according to claim 4, 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. Wherein, the organic light-emitting device further comprises: A color filter layer is disposed between the substrate and the organic light emitting diode or on the organic light emitting diode and corresponds to the red pixel, the green pixel, and the blue pixel.

10. The organic light-emitting device according to claim 4, wherein: The first compound is a compound of formula 8: [Molecular formula 8] 11. A luminescent compound represented by a compound in Formula 6: [Formula 6] 12. An organic light-emitting device, comprising: substrate; and an organic light emitting diode located on the substrate and comprising a first electrode, a second electrode facing the first electrode, and a first light emitting material layer including a compound and located between the first electrode and the second electrode, Wherein, the compound is the luminescent compound described in claim 11.

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