Emitting compound and orgnic light emitting device including the same

Abstract

The present invention provides a luminescent compound represented by the following chemical formula, an organic light-emitting diode comprising the same, and an organic light-emitting device.

Description

Technology Field

[0001] The present invention relates to a luminescent compound, and more specifically, to a luminescent compound having high luminescent efficiency and lifespan, and to an organic light-emitting diode and an organic light-emitting device containing the same. Background Technology

[0003] With the recent increase in the size of display devices, there is a growing demand for flat display devices that take up less space, and as one such flat display device, the technology of organic light-emitting diodes (OLEDs) is developing rapidly.

[0004] An organic light-emitting diode (OLED) is a device that emits light when electrons and holes are injected from the cathode and anode into a light-emitting material layer formed between the electron injection electrode (cathode) and the hole injection electrode (anode), and subsequently annihilate each other. It has the advantages of being able to be formed on flexible transparent substrates such as plastic, operating at low voltages (below 10V), consuming relatively little power, and offering excellent color quality.

[0005] For example, an organic light-emitting display device includes red pixels, green pixels, and blue pixels, and an organic light-emitting diode is formed in each pixel.

[0006] However, blue organic light-emitting diodes cannot achieve sufficient luminous efficiency and lifespan, and consequently, organic light-emitting display devices also have limitations in luminous efficiency and lifespan. The problem to be solved

[0008] The present invention aims to solve the problems of low luminous efficiency and short lifespan in conventional organic light-emitting diodes and organic light-emitting devices. means of solving the problem

[0010] To solve the above problem, the present invention comprises: a ring represented by Chemical Formula 1, wherein X is one of B, P=O, or P=S; Y1 is one of NR1, C(R2)2, O, S, Se, or Si(R3)2; Y2 is O or S; each of R1 to R6 is independently selected from hydrogen, deuterium, an unsubstituted or deuterium-substituted C1 to C10 alkyl group, an unsubstituted or deuterium-substituted or C1 to C10 alkyl group arylamine group of C6 to C30 substituted with a deuterium or C1 to C10 alkyl group, an unsubstituted or deuterium-substituted or C1 to C10 aryl group aryl group of C6 to C30 substituted with a deuterium or C1 to C10 alkyl group, or a unsubstituted or deuterium-substituted or C5 to C30 heteroaryl group alkyl group of C5 to C30 substituted with a deuterium or C1 to C10 alkyl group; and each of the A ring, B ring, and C ring is independently a substituted or unsubstituted cycloalkyl ring of six elements, a substituted or unsubstituted aromatic ring of six elements, or a substituted or unsubstituted The present invention provides a luminescent compound characterized by being selected from a heteroaromatic ring of six elements.

[0011] [Chemical Formula 1]

[0012]

[0013] The above chemical formula 1 is represented by chemical formula 2-1, wherein in chemical formula 2-1, R7, R8, and R9 are each independently selected from hydrogen, deuterium, a C1 to C10 alkyl group that is unsubstituted or substituted with deuterium, a C6 to C30 arylamine group that is unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, a C6 to C30 aryl group that is unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, and a C6 to C30 heteroaryl group that is unsubstituted or substituted with deuterium or a C1 to C10 alkyl group.

[0014] [Chemical Formula 2-1]

[0015]

[0016] The above chemical formula 2-1 is characterized by being represented by chemical formula 2-2.

[0017] [Chemical Formula 2-2]

[0018]

[0019] The above Chemical Formula 1 is represented by the following Chemical Formula 2-3, wherein in Chemical Formula 2-3, each of Z1 to Z4 is independently N or CR 10 Igo, R7, R8, R9, R 10 Each is characterized by being independently selected from hydrogen, deuterium, an unsubstituted or deuterium-substituted C1 to C10 alkyl group, an unsubstituted or deuterium-substituted C6 to C30 arylamine group substituted with a deuterium or C1 to C10 alkyl group, an unsubstituted or deuterium or C1 to C10 aryl group substituted with a C6 to C30 aryl group, or an unsubstituted or deuterium or C1 to C10 alkyl group substituted with a C6 to C30 heteroaryl group.

[0020] [Chemical Formula 2-3]

[0021]

[0022] The above chemical formula 2-3 is characterized by being represented by chemical formula 2-4.

[0023] [Chemical Formula 2-4]

[0024]

[0025] In another aspect, the present invention comprises: a substrate; a first electrode; and a second electrode facing the first electrode; The apparatus comprises an organic light-emitting diode positioned on a substrate, the first light-emitting material layer comprising a first compound and positioned between the first electrode and the second electrode, wherein the first compound is represented by Chemical Formula 1, X is one of B, P=O, P=S, Y1 is one of NR1, C(R2)2, O, S, Se, Si(R3)2, Y2 is O or S, and R1 to R6 are each independently selected from hydrogen, deuterium, an unsubstituted or deuterium-substituted C1 to C10 alkyl group, an unsubstituted or deuterium-substituted C6 to C30 arylamine group substituted with a deuterium or C1 to C10 alkyl group, an unsubstituted or deuterium-substituted C6 to C30 aryl group substituted with a deuterium or C1 to C10 alkyl group, and a C5 to C30 heteroaryl group substituted with a deuterium or C1 to C10 alkyl group, and A ring, B ring The present invention provides an organic light-emitting device characterized in that each of the C rings is independently selected from a cycloalkyl ring of six elements that is substituted or unsubstituted, an aromatic ring of six elements that is substituted or unsubstituted, and a heteroaromatic ring of six elements that is substituted or unsubstituted.

[0026] [Chemical Formula 1]

[0027]

[0028] In the organic light-emitting device of the present invention, the above formula 1 is represented by formula 2-1, and in formula 2-1, each of R7, R8, and R9 is independently selected from hydrogen, deuterium, a C1 to C10 alkyl group that is not substituted or is substituted with deuterium, a C6 to C30 arylamine group that is not substituted or is substituted with deuterium or a C1 to C10 alkyl group, an C6 to C30 aryl group that is not substituted or is substituted with deuterium or a C1 to C10 alkyl group, and a C6 to C30 heteroaryl group that is not substituted or is substituted with deuterium or a C1 to C10 alkyl group.

[0029] [Chemical Formula 2-1]

[0030]

[0031] In the organic light-emitting device of the present invention, the chemical formula 2-1 is characterized by being represented by chemical formula 2-2.

[0032] [Chemical Formula 2-2]

[0033]

[0034] In the organic light-emitting device of the present invention, the above chemical formula 1 is represented by the following chemical formula 2-3, and in the above chemical formula 2-3, each of Z1 to Z4 is independently N or CR 10 Igo, R7, R8, R9, R 10 Each is characterized by being independently selected from hydrogen, deuterium, an unsubstituted or deuterium-substituted C1 to C10 alkyl group, an unsubstituted or deuterium-substituted C6 to C30 arylamine group substituted with a deuterium or C1 to C10 alkyl group, an unsubstituted or deuterium or C1 to C10 aryl group substituted with a C6 to C30 aryl group, or an unsubstituted or deuterium or C1 to C10 alkyl group substituted with a C6 to C30 heteroaryl group.

[0035] [Chemical Formula 2-3]

[0036]

[0037] In the organic light-emitting device of the present invention, the chemical formula 2-3 is characterized by being represented by chemical formula 2-4.

[0038] [Chemical Formula 2-4]

[0039]

[0040] In the organic light-emitting device of the present invention, the first light-emitting material layer further comprises a second compound, wherein the second compound is represented by Chemical Formula 4, and in Chemical Formula 4, Ar1 and Ar2 are each independently C6-C 30 aryl group or C5-C 30 It is a heteroaryl group, and L is a single bond or C6-C 20 It is an arylene group, characterized in that hydrogen is not substituted or is partially or entirely substituted with deuterium.

[0041] [Chemical Formula 4]

[0042]

[0043] In the organic light-emitting device of the present invention, the organic light-emitting diode further comprises a second light-emitting material layer located between the first light-emitting material layer and the second electrode, the second light-emitting material layer comprising a third compound; and a first charge-generating layer located between the first light-emitting material layer and the second light-emitting material layer, wherein the third compound is represented by the chemical formula 1.

[0044] The organic light-emitting device of the present invention is characterized in that, in the substrate, a red pixel, a green pixel, and a blue pixel are defined, and the organic light-emitting diode corresponds to the red pixel, the green pixel, and the blue pixel, and further comprises a color conversion layer provided between the substrate and the organic light-emitting diode or on top of the organic light-emitting diode corresponding to the red pixel and the green pixel.

[0045] In the organic light-emitting device of the present invention, the organic light-emitting diode further comprises a third light-emitting material layer located between the first charge generating layer and the second light-emitting material layer, and a second charge generating layer located between the second light-emitting material layer and the third light-emitting material layer, wherein the third light-emitting material layer emits yellow-green light or emits red and green light.

[0046] In the organic light-emitting device of the present invention, the organic light-emitting diode further comprises a second light-emitting material layer located between the first light-emitting material layer and the second electrode, which emits a yellow-green color, and a first charge-generating layer located between the first light-emitting material layer and the second light-emitting material layer.

[0047] The organic light-emitting device of the present invention is characterized in that, in the substrate, a red pixel, a green pixel, and a blue pixel are defined, and the organic light-emitting diode corresponds to the red pixel, the green pixel, and the blue pixel, and further comprises a color filter layer provided between the substrate and the organic light-emitting diode or on top of the organic light-emitting diode corresponding to the red pixel, the green pixel, and the blue pixel. Effects of the invention

[0049] The luminescent compound of the present invention is a polycyclic aromatic compound and has a significantly improved lifespan.

[0050] Accordingly, the organic light-emitting diode and organic light-emitting device containing the light-emitting compound of the present invention have an improved lifespan without a significant increase in driving voltage or a decrease in luminous efficiency. Brief explanation of the drawing

[0052] FIG. 1 is a schematic circuit diagram of an organic light-emitting display device according to an embodiment of the present invention. FIG. 2 is a schematic cross-sectional view of an organic light-emitting display device according to a first embodiment of the present invention. FIG. 3 is a schematic cross-sectional view of an organic light-emitting diode used in an organic light-emitting display device according to the first embodiment of the present invention. FIG. 4 is a schematic cross-sectional view of a double-stack structured organic light-emitting diode used in an organic light-emitting display device according to the first embodiment of the present invention. FIG. 5 is a schematic cross-sectional view of an organic light-emitting display device according to a second embodiment of the present invention. FIG. 6 is a schematic cross-sectional view of a double-stack structured organic light-emitting diode used in an organic light-emitting display device according to a second embodiment of the present invention. FIG. 7 is a schematic cross-sectional view of a triple-stack structured organic light-emitting diode used in an organic light-emitting display device according to a second embodiment of the present invention. FIG. 8 is a schematic cross-sectional view of an organic light-emitting display device according to a third embodiment of the present invention. Specific details for implementing the invention

[0053] Hereinafter, preferred embodiments according to the present invention will be described with reference to the drawings.

[0054] FIG. 1 is a schematic circuit diagram of an organic light-emitting display device according to an embodiment of the present invention.

[0055] As illustrated in FIG. 1, in an organic light-emitting display device, gate wiring (GL), data wiring (DL), and power wiring (PL) are formed to intersect each other and define pixels (P), and in the pixels (P), a switching thin-film transistor (Ts), a driving thin-film transistor (Td), a storage capacitor (Cst), and an organic light-emitting diode (D) are formed. The pixels (P) may include red pixels, green pixels, and blue pixels.

[0056] The switching thin-film transistor (Ts) is connected to the gate wiring (GL) and data wiring (DL), and the driving thin-film transistor (Td) and storage capacitor (Cst) are connected between the switching thin-film transistor (Ts) and the power wiring (PL). The organic light-emitting diode (D) is connected to the driving thin-film transistor (Td).

[0057] In this organic light-emitting display device, when the switching thin-film transistor (Ts) is turned on according to the gate signal applied to the gate wiring (GL), the data signal applied to the data wiring (DL) is applied to the gate electrode of the driving thin-film transistor (Td) and one electrode of the storage capacitor (Cst) through the switching thin-film transistor (Ts).

[0058] The driving thin-film transistor (Td) is turned on according to a data signal applied to the gate electrode, and as a result, a current proportional to the data signal flows from the power wiring (PL) through the driving thin-film transistor (Td) to the organic light-emitting diode (D), and the organic light-emitting diode (D) emits light with a brightness proportional to the current flowing through the driving thin-film transistor (Td).

[0059] At this time, the storage capacitor (Cst) is charged with a voltage proportional to the data signal so that the voltage of the gate electrode of the driving thin-film transistor (Td) is maintained constant during one frame.

[0060] Therefore, the organic light-emitting display device can display a desired image.

[0061] FIG. 2 is a schematic cross-sectional view of the organic light-emitting display device of the present invention.

[0062] As illustrated in FIG. 2, the organic light-emitting display device (100) includes a thin-film transistor (Tr) located on a substrate (110) and an organic light-emitting diode (D) connected to the thin-film transistor (Tr). For example, red pixels, green pixels, and blue pixels are defined on the substrate (110), and an organic light-emitting diode (D) is located at each pixel. That is, an organic light-emitting diode (D) emitting red, green, and blue light is provided at the red pixel, green pixel, and blue pixel.

[0063] The substrate (110) may be a glass substrate or a flexible substrate. For example, the flexible substrate may be any one of a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylenenaphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate, and a polycarbonate (PC) substrate.

[0064] A buffer layer (120) is formed on the substrate (110), and a thin-film transistor (Tr) is formed on the buffer layer (120). The buffer layer (120) may be omitted.

[0065] A semiconductor layer (122) is formed on the buffer layer (120). The semiconductor layer (122) may be made of an oxide semiconductor material or polycrystalline silicon.

[0066] If the semiconductor layer (122) is made of an oxide semiconductor material, a light-blocking pattern (not shown) may be formed on the lower part of the semiconductor layer (122), and the light-blocking pattern prevents light from being incident on the semiconductor layer (122) so as not to degrade the semiconductor layer (122) due to light. Alternatively, the semiconductor layer (122) may be made of polycrystalline silicon, in which case impurities may be doped on both edges of the semiconductor layer (122).

[0067] A gate insulating film (124) made of an insulating material is formed on the upper surface of the semiconductor layer (122). The gate insulating film (124) may be made of an inorganic insulating material such as silicon oxide or silicon nitride.

[0068] On the upper part of the gate insulating film (124), a gate electrode (130) made of a conductive material such as metal is formed corresponding to the center of the semiconductor layer (122).

[0069] In FIG. 2, the gate insulating film (124) is formed on the front surface of the substrate (110), but the gate insulating film (124) may be patterned in the same shape as the gate electrode (130).

[0070] An interlayer insulating film (132) made of an insulating material is formed on the upper part of the gate electrode (130). The interlayer insulating film (132) may be formed of an inorganic insulating material such as silicon oxide or silicon nitride, or may be formed of an organic insulating material such as benzocyclobutene or photoacryl.

[0071] The interlayer insulating film (132) has first and second contact holes (134, 136) that expose both sides of the semiconductor layer (122). The first and second contact holes (134, 136) are located on both sides of the gate electrode (130) and spaced apart from the gate electrode (130).

[0072] Here, the first and second contact holes (134, 136) are also formed within the gate insulating film (124). Alternatively, if the gate insulating film (124) is patterned in the same shape as the gate electrode (130), the first and second contact holes (134, 136) may be formed only within the interlayer insulating film (132).

[0073] On the interlayer insulating film (132), a source electrode (140) and a drain electrode (142) made of a conductive material such as metal are formed.

[0074] The source electrode (140) and the drain electrode (142) are spaced apart from the gate electrode (130) and contact both sides of the semiconductor layer (122) through the first and second contact holes (134, 136), respectively.

[0075] The semiconductor layer (122), the gate electrode (130), the source electrode (140), and the drain electrode (142) form a thin-film transistor (Tr), and the thin-film transistor (Tr) functions as a driving element.

[0076] The thin-film transistor (Tr) has a coplanar structure in which a gate electrode (130), a source electrode (142), and a drain electrode (144) are located on top of a semiconductor layer (122).

[0077] In contrast, the thin-film transistor (Tr) can have an inverted staggered structure in which the gate electrode is located below the semiconductor layer and the source and drain electrodes are located above the semiconductor layer. In this case, the semiconductor layer can be made of amorphous silicon.

[0078] Although not illustrated, gate wiring and data wiring intersect to define a pixel, and switching elements connected to the gate wiring and data wiring are further formed. The switching elements are connected to thin-film transistors (Tr), which are driving elements.

[0079] In addition, power wiring is formed spaced apart from data wiring or parallel to data wiring, and a storage capacitor may be further configured to maintain a constant voltage of the gate electrode of a thin-film transistor (Tr), which is a driving element, during one frame.

[0080] A protective layer (150) having a drain contact hole (152) that exposes the drain electrode (142) of the thin-film transistor (Tr) is formed to cover the thin-film transistor (Tr).

[0081] On the protective layer (150), a first electrode (160) connected to the drain electrode (142) of the thin-film transistor (Tr) through a drain contact hole (152) is formed separately for each pixel area. The first electrode (160) may be an anode and may be made of a conductive material with a relatively large work function value, for example, a transparent conductive oxide (TCO). Specifically, the first electrode (160) may be made of indium-tin-oxide (ITO), indium-zinc-oxide (IZO), indium-tin-zinc-oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium-copper-oxide (ICO), and aluminum:zinc oxide (Al:ZnO; AZO).

[0082] In the case where the organic light-emitting display device (100) of the present invention is of the bottom-emission type, the first electrode (160) may have a single-layer structure made of a transparent conductive oxide. Alternatively, in the case where the organic light-emitting display device (100) of the present invention is of the top-emission type, a reflective electrode or a reflective layer may be further formed below the first electrode (160). For example, the reflective electrode or the reflective layer may be made of silver (Ag) or an aluminum-palladium-copper (APC) alloy. In the top-emission type organic light-emitting display device (100), the first electrode (160) may have a triple-layer structure of ITO / Ag / ITO or ITO / APC / ITO.

[0083] Additionally, a bank layer (166) covering the edge of the first electrode (160) is formed on the protective layer (150). The bank layer (166) exposes the center of the first electrode (160) corresponding to the pixel.

[0084] An organic light-emitting layer (162) is formed on the first electrode (160). The organic light-emitting layer (162) may have a single-layer structure of an emitting material layer made of a light-emitting material. Additionally, to increase the light-emitting efficiency, the organic light-emitting layer (162) may have a multi-layer structure.

[0085] The organic light-emitting layer (162) is positioned separately in the red pixel, the green pixel, and the blue pixel. As described below, the organic light-emitting layer (162) in the blue pixel contains a light-emitting compound represented by Chemical Formula 1, and accordingly, the lifespan of the organic light-emitting diode (D) in the blue pixel is greatly improved.

[0086] A second electrode (164) is formed on the upper surface of a substrate (110) on which an organic light-emitting layer (162) is formed. The second electrode (164) is located on the front surface of the display area and is made of a conductive material with a relatively small work function value and can be used as a cathode. For example, the second electrode (164) may be made of aluminum (Al), magnesium (Mg), silver (Ag), or an alloy thereof, for example, an aluminum-magnesium alloy (AlMg) or a silver-magnesium alloy (MgAg). When the organic light-emitting display device (100) is of the top-emitting type, the second electrode (164) has a thin thickness and has light-transmitting (semi-transmitting) characteristics.

[0087] The first electrode (160), the organic light-emitting layer (162), and the second electrode (164) form an organic light-emitting diode (D).

[0088] On the second electrode (164), an encapsulation film (170) is formed to prevent external moisture from penetrating into the organic light-emitting diode (D). The encapsulation film (170) may have a laminated structure of a first inorganic insulating layer (172), an organic insulating layer (174), and a second inorganic insulating layer (174), but is not limited thereto. Additionally, the encapsulation film (170) may be omitted.

[0089] The organic light-emitting display device (100) may further include a polarizing plate (not shown) to reduce the reflection of external light. For example, the polarizing plate (not shown) may be a circular polarizing plate. If the organic light-emitting display device (100) is a bottom-emitting type, the polarizing plate may be located below the substrate (110). Meanwhile, if the organic light-emitting display device (100) of the present invention is a top-emitting type, the polarizing plate may be located above the encapsulation film (170).

[0090] In addition, in the top-emitting type organic light-emitting display device (100), a cover window (not shown) may be attached to an encapsulation film (170) or a polarizing plate. At this time, the substrate (110) and the cover window may have flexible characteristics to form a flexible display device.

[0091] FIG. 3 is a schematic cross-sectional view of an organic light-emitting diode according to an embodiment of the present invention.

[0092] As illustrated in FIG. 3, an organic light-emitting diode (D) according to an embodiment of the present invention comprises first and second electrodes (160, 164) facing each other and an organic light-emitting layer (162) located between them, and the organic light-emitting layer (162) may include a light-emitting material layer (240) located between the first and second electrodes (160, 164). An organic light-emitting display device (100 of FIG. 2) includes a red pixel, a green pixel, and a blue pixel, and the organic light-emitting diode (D) may be located in the blue pixel.

[0093] One of the first electrode (160) and the second electrode (164) may be an anode, and the other of the first electrode (160) and the second electrode (164) may be a cathode. Additionally, one of the first electrode (160) and the second electrode (164) may be a transmissive electrode (semitransmissive electrode), and the other of the first electrode (160) and the second electrode (164) may be a reflective electrode.

[0094] Additionally, the organic light-emitting layer (162) may further include an electron blocking layer (230) located between the first electrode (160) and the light-emitting material layer (240), and a hole blocking layer (250) located between the light-emitting material layer (240) and the second electrode (164).

[0095] Additionally, the organic light-emitting layer (162) may include a hole transporting layer (220) located between the first electrode (160) and the electron blocking layer (230).

[0096] Additionally, the organic light-emitting layer (162) may further include a hole injection layer (210) located between the first electrode (160) and the hole transport layer (220), and an electron injection layer (260) located between the second electrode (164) and the hole blocking layer (250).

[0097] The luminescent material layer (240) includes a luminescent compound (first compound, 242) which is a polycyclic aromatic compound. The luminescent compound of the present invention is represented by Chemical Formula 1.

[0098] [Chemical Formula 1]

[0099]

[0100] In Chemical Formula 1, X is one of B, P=O, P=S, Y1 is one of NR1, C(R2)2, O, S, Se, Si(R3)2, and Y2 is O or S. Each of R1 to R6 is independently selected from hydrogen, deuterium, C1 to C10 alkyl groups that are unsubstituted or substituted with deuterium, C6 to C30 arylamines that are unsubstituted or substituted with deuterium or C1 to C10 alkyl groups, C6 to C30 aryl groups that are unsubstituted or substituted with deuterium or C1 to C10 alkyl groups, and C5 to C30 heteroaryl groups that are unsubstituted or substituted with deuterium or C1 to C10 alkyl groups.

[0101] Each of the A ring, B ring, and C ring is independently selected from a substituted or unsubstituted 6-element cycloalkyl ring, a substituted or unsubstituted 6-element aromatic ring, or a substituted or unsubstituted 6-element heteroaromatic ring. In each of the A ring, B ring, and C ring, hydrogen may be substituted with at least one of deuterium, a C1 to C10 alkyl group, a C6 to C30 aryl group, or a C5 to C30 heteroaryl group.

[0102] For example, the C1 to C10 alkyl group may be selected from methyl, ethyl, and tertiarybutyl, and the C6 to C30 aryl group may be selected from phenyl, naphthyl, and biphenyl. Additionally, the C6 to C30 arylamine group may be diphenylamine, and the C5 to C30 heteroaryl group may be selected from dibenzofuranyl, dibenzothiophenyl, and carbazoyl. The 6-element cycloalkyl ring may be a cyclopentane ring or a cyclohexane ring, the 6-element aromatic ring may be a benzene ring, and the 6-element heteroaromatic ring may be a pyridine ring.

[0103] For example, in Chemical Formula 1, ring A and ring B can each be a cyclohexane ring, and ring C can be a benzene ring. That is, the luminescent compound of Chemical Formula 1 can be represented by Chemical Formula 2-1.

[0104] [Chemical Formula 2-1]

[0105]

[0106] In Chemical Formula 2-1, R7, R8, and R9 can each be independently selected from hydrogen, deuterium, an unsubstituted or deuterium-substituted C1 to C10 alkyl group, an unsubstituted or deuterium-substituted C6 to C30 arylamine group substituted with a deuterium or C1 to C10 alkyl group, an unsubstituted or deuterium or C1 to C10 aryl group substituted with a C6 to C30 aryl group, or an unsubstituted or deuterium or C1 to C10 alkyl group substituted with a C6 to C30 heteroaryl group.

[0107] In addition, in Chemical Formula 2-1, X can be B and Y1 can be NR1. That is, the luminescent compound of Chemical Formula 1 can be represented by Chemical Formula 2-2.

[0108] [Chemical Formula 2-2]

[0109]

[0110] For example, in Formula 2-2, R1 may be a C6 to C30 aryl group (e.g., phenyl) substituted with a C1 to C10 alkyl group (e.g., tertiarybutyl) or a C5 to C30 heteroaryl group (e.g., dibenzofuranyl) substituted with a C1 to C10 alkyl group (e.g., tertiarybutyl). Additionally, two of R4 to R6 may be hydrogen and the other may be a C6 to C30 arylamine group (e.g., diphenylamine) substituted with a C1 to C10 alkyl group (e.g., tertiarybutyl) or a C1 to C10 alkyl group (e.g., tertiarybutyl). Additionally, R7 may be a C1 to C10 alkyl group (e.g., tertiarybutyl), and R8 and R9 may be hydrogen.

[0111] Meanwhile, in Chemical Formula 1, ring A is a heteroaromatic ring of six elements, and ring B and ring C can each be a benzene ring. That is, the luminescent compound of Chemical Formula 1 can be represented by Chemical Formula 2-3.

[0112] [Chemical Formula 2-3]

[0113]

[0114] In Chemical Formula 2-3, each of Z1 to Z4 is independently N or CR 10 It could be, R7, R8, R9, R 10 Each may be independently selected from hydrogen, deuterium, an unsubstituted or deuterium-substituted C1 to C10 alkyl group, an unsubstituted or deuterium-substituted C6 to C30 arylamine group substituted with a deuterium or C1 to C10 alkyl group, an unsubstituted or deuterium or C1 to C10 aryl group substituted with a C6 to C30 aryl group, or an unsubstituted or deuterium or C1 to C10 alkyl group substituted with a C6 to C30 heteroaryl group.

[0115] In addition, in Chemical Formula 2-3, X can be B and Y1 can be NR1. That is, the luminescent compound of Chemical Formula 1 can be represented by Chemical Formula 2-4.

[0116] [Chemical Formula 2-4]

[0117]

[0118] For example, in Chemical Formula 2-4, R1 may be a C6 to C30 aryl group (e.g., phenyl or biphenyl) or a C5 to C30 heteroaryl group (e.g., dibenzofuranyl). Additionally, R4 to R9 are hydrogen, and one of Z1 to Z4 may be N.

[0119] The first compound (242), which is the luminescent compound of the present invention shown in Chemical Formula 1, may be one of the compounds of Chemical Formula 3.

[0120] [Chemical Formula 3]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127] The luminescent compound of the present invention shown in Chemical Formula 1 emits blue light and is used in the luminescent material layer (240) of an organic light-emitting diode (D), thereby greatly increasing the lifespan of the organic light-emitting diode (D) and the organic light-emitting device (100).

[0128] [Synthetic Example]

[0129] 1. Synthesis of Compound 1-1

[0130] (1) Compound I1-1c

[0131] [Reaction Equation 1-1]

[0132]

[0133] 12.9 g (50 mmol) of Compound I1-1a, 25.9 g (50 mmol) of Compound I1-1b, 0.45 g (2 mmol) of Palladium Acetate, 18.9 g (196 mmol) of Sodium Tertiary Butoxide, 0.8 g (4 mmol) of Tritertiary Butylphosphine, and 300 mL of Toluene were added to a 500 mL reactor and stirred under reflux for 5 hours. After the reaction was complete, the mixture was filtered, the filtrate was concentrated, and separated by column chromatography to obtain 19.2 g of Compound I1-1c (yield 52%).

[0134] (2) Compound 1-1

[0135] [Reaction Equation 1-2]

[0136]

[0137] 9.2 g (12.5 mmol) of Compound I1-1c and 60 mL of tert-butylbenzene were added to a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78 °C. After the dropwise addition, the mixture was stirred at 60 °C for 3 hours. Subsequently, nitrogen was blown at 60 °C to remove heptane. 6.3 g (25 mmol) of boron tribromide was added dropwise at -78 °C. After the dropwise addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was added dropwise at 0 °C. After the dropwise addition, the mixture was stirred at 120 °C for 2 hours. After the reaction was complete, an aqueous sodium acetate solution was added at room temperature and stirred. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.3 g of Compound I1-1 (yield 15%).

[0138] 2. Synthesis of Compounds 1-3

[0139] (1) Compound I1-3c

[0140] [Reaction Equation 2-1]

[0141]

[0142] 24.0 g (50 mmol) of Compound I1-3a, 25.8 g (50 mmol) of Compound I1-3b, 0.45 g (2 mmol) of Palladium Acetate, 18.9 g (196 mmol) of Sodium Tertiary Butoxide, 0.8 g (4 mmol) of Tritertiary Butylphosphine, and 300 mL of Toluene were added to a 500 mL reactor and stirred under reflux for 5 hours. After the reaction was complete, the mixture was filtered, the filtrate was concentrated, and separated by column chromatography to obtain 22.1 g of Compound I1-3c. (Yield 46%)

[0143] (2) Compound 1-3

[0144] [Reaction Equation 2-2]

[0145]

[0146] 12.0 g (12.5 mmol) of Compound I1-3c and 60 mL of tert-butylbenzene were added to a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78 °C. After the addition, the mixture was stirred at 60 °C for 3 hours. Subsequently, nitrogen was blown at 60 °C to remove heptane. 6.3 g (25 mmol) of boron tribromide was added dropwise at -78 °C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was added dropwise at 0 °C. After the addition, the mixture was stirred at 120 °C for 2 hours. After the reaction was complete, an aqueous sodium acetate solution was added at room temperature and stirred. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.4 g of Compound I1-3 (yield 12%).

[0147] 3. Synthesis of Compounds 1-4

[0148] (1) Compound I1-4c

[0149] [Reaction Equation 3-1]

[0150]

[0151] 24.0 g (50 mmol) of Compound I1-4a, 30.3 g (50 mmol) of Compound I1-4b, 0.45 g (2 mmol) of Palladium Acetate, 18.9 g (196 mmol) of Sodium Tertiary Butoxide, 0.8 g (4 mmol) of Tritertiary Butylphosphine, and 300 mL of Toluene were added to a 500 mL reactor and stirred under reflux for 5 hours. After the reaction was complete, the mixture was filtered, the filtrate was concentrated, and separated by column chromatography to obtain 25.2 g of Compound I1-4c. (Yield 48%)

[0152] (2) Compound 1-4

[0153] [Reaction Equation 3-2]

[0154]

[0155] 13.1 g (12.5 mmol) of Compound I1-4c and 60 mL of tert-butylbenzene were added to a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78 °C. After the addition, the mixture was stirred at 60 °C for 3 hours. Subsequently, nitrogen was blown at 60 °C to remove heptane. 6.3 g (25 mmol) of boron tribromide was added dropwise at -78 °C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was added dropwise at 0 °C. After the addition, the mixture was stirred at 120 °C for 2 hours. After the reaction was complete, an aqueous sodium acetate solution was added at room temperature and stirred. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.8 g of Compound I1-4 (yield 14%).

[0156] 4. Synthesis of Compounds 1-6

[0157] (1) Compound I1-6c

[0158] [Reaction Equation 4-1]

[0159]

[0160] 12.9 g (50 mmol) of Compound I1-6a, 23.3 g (50 mmol) of Compound I1-6b, 0.45 g (2 mmol) of Palladium Acetate, 18.9 g (196 mmol) of Sodium Tertiary Butoxide, 0.8 g (4 mmol) of Tritertiary Butylphosphine, and 300 mL of Toluene were added to a 500 mL reactor and stirred under reflux for 5 hours. After the reaction was complete, the solution was filtered, the filtrate was concentrated, and separated by column chromatography to obtain 16.2 g of Compound I1-6c (yield 45%).

[0161] (2) Compound 1-6

[0162] [Reaction Equation 4-2]

[0163]

[0164] 9.0 g (12.5 mmol) of Compound I1-6c and 60 mL of tert-butylbenzene were added to a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78 °C. After the addition, the mixture was stirred at 60 °C for 3 hours. Subsequently, nitrogen was blown at 60 °C to remove heptane. 6.3 g (25 mmol) of boron tribromide was added dropwise at -78 °C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was added dropwise at 0 °C. After the addition, the mixture was stirred at 120 °C for 2 hours. After the reaction was complete, an aqueous sodium acetate solution was added at room temperature and stirred. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.0 g of Compound I1-6 (yield 11%).

[0165] 5. Synthesis of Compounds 1-7

[0166] (1) Compound I1-7c

[0167] [Reaction Equation 5-1]

[0168]

[0169] 24.0 g (50 mmol) of Compound I1-7a, 25.0 g (50 mmol) of Compound I1-7b, 0.45 g (2 mmol) of Palladium Acetate, 18.9 g (196 mmol) of Sodium Tertiary Butoxide, 0.8 g (4 mmol) of Tritertiary Butylphosphine, and 300 mL of Toluene were added to a 500 mL reactor and stirred under reflux for 5 hours. After the reaction was complete, the mixture was filtered, the filtrate was concentrated, and separated by column chromatography to obtain 22.7 g of Compound I1-7c. (Yield 48%)

[0170] (2) Compound 1-7

[0171] [Reaction Equation 5-2]

[0172]

[0173] 11.8 g (12.5 mmol) of Compound I1-7c and 60 mL of tert-butylbenzene were added to a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78 °C. After the addition, the mixture was stirred at 60 °C for 3 hours. Subsequently, nitrogen was blown at 60 °C to remove heptane. 6.3 g (25 mmol) of boron tribromide was added dropwise at -78 °C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was added dropwise at 0 °C. After the addition, the mixture was stirred at 120 °C for 2 hours. After the reaction was complete, an aqueous sodium acetate solution was added at room temperature and stirred. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.5 g of Compound I1-7 (yield 13%).

[0174] 6. Synthesis of Compound 2-2

[0175] (1) Compound I2-2c

[0176] [Reaction Equation 6-1]

[0177]

[0178] 8.4 g (50 mmol) of Compound I2-2a, 18.5 g (50 mmol) of Compound I2-2b, 0.45 g (2 mmol) of Palladium Acetate, 18.9 g (196 mmol) of Sodium Tertiary Butoxide, 0.8 g (4 mmol) of Tritertiary Butylphosphine, and 300 mL of Toluene were added to a 500 mL reactor and stirred under reflux for 5 hours. After the reaction was complete, the mixture was filtered, the filtrate was concentrated, and separated by column chromatography to obtain 12.8 g of Compound I2-2c. (Yield 51%)

[0179] (2) Compound 2-2

[0180] [Reaction Equation 6-2]

[0181]

[0182] 6.3 g (12.5 mmol) of Compound I2-2c and 60 mL of tert-butylbenzene were added to a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78 °C. After the addition, the mixture was stirred at 60 °C for 3 hours. Subsequently, nitrogen was blown at 60 °C to remove heptane. 6.3 g (25 mmol) of boron tribromide was added dropwise at -78 °C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was added dropwise at 0 °C. After the addition, the mixture was stirred at 120 °C for 2 hours. After the reaction was complete, an aqueous sodium acetate solution was added at room temperature and stirred. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 0.8 g of Compound 2-2 (yield 14%).

[0183] 7. Synthesis of Compound 2-3

[0184] (1) Compound I2-3c

[0185] [Reaction Equation 7-1]

[0186]

[0187] 8.4 g (50 mmol) of Compound I2-3a, 18.5 g (50 mmol) of Compound I2-3b, 0.45 g (2 mmol) of Palladium Acetate, 18.9 g (196 mmol) of Sodium Tertiary Butoxide, 0.8 g (4 mmol) of Tritertiary Butylphosphine, and 300 mL of Toluene were added to a 500 mL reactor and stirred under reflux for 5 hours. After the reaction was complete, the mixture was filtered, the filtrate was concentrated, and separated by column chromatography to obtain 14.6 g of Compound I2-3c (yield 58%).

[0188] (2) Compound 2-3

[0189] [Reaction Equation 7-2]

[0190]

[0191] 6.3 g (12.5 mmol) of Compound I2-3c and 60 mL of tert-butylbenzene were added to a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78 °C. After the addition, the mixture was stirred at 60 °C for 3 hours. Subsequently, nitrogen was blown at 60 °C to remove heptane. 6.3 g (25 mmol) of boron tribromide was added dropwise at -78 °C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was added dropwise at 0 °C. After the addition, the mixture was stirred at 120 °C for 2 hours. After the reaction was complete, an aqueous sodium acetate solution was added at room temperature and stirred. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.2 g of Compound 2-3 (yield 20%).

[0192] 8. Synthesis of Compound 2-5

[0193] (1) Compound I2-5c

[0194] [Reaction Equation 8-1]

[0195]

[0196] 8.4 g (50 mmol) of Compound I2-5a, 23.0 g (50 mmol) of Compound I2-5b, 0.45 g (2 mmol) of Palladium Acetate, 18.9 g (196 mmol) of Sodium Tertiary Butoxide, 0.8 g (4 mmol) of Tritertiary Butylphosphine, and 300 mL of Toluene were added to a 500 mL reactor and stirred under reflux for 5 hours. After the reaction was complete, the mixture was filtered, the filtrate was concentrated, and separated by column chromatography to obtain 16.2 g of Compound I2-5c (Yield 55%).

[0197] (2) Compound 2-5

[0198] [Reaction Equation 8-2]

[0199]

[0200] 7.4 g (12.5 mmol) of Compound I2-5c and 60 mL of tert-butylbenzene were added to a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78 °C. After the addition, the mixture was stirred at 60 °C for 3 hours. Subsequently, nitrogen was blown at 60 °C to remove heptane. 6.3 g (25 mmol) of boron tribromide was added dropwise at -78 °C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was added dropwise at 0 °C. After the addition, the mixture was stirred at 120 °C for 2 hours. After the reaction was complete, an aqueous sodium acetate solution was added at room temperature and stirred. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.3 g of Compound I2-5 (yield 18%).

[0201] 9. Synthesis of Compound 2-7

[0202] (1) Compound I2-7c

[0203] [Reaction Equation 9-1]

[0204]

[0205] 8.4 g (50 mmol) of Compound I2-7a, 17.7 g (50 mmol) of Compound I2-7b, 0.45 g (2 mmol) of Palladium Acetate, 18.9 g (196 mmol) of Sodium Tertiary Butoxide, 0.8 g (4 mmol) of Tritertiary Butylphosphine, and 300 mL of Toluene were added to a 500 mL reactor and stirred under reflux for 5 hours. After the reaction was complete, the mixture was filtered, the filtrate was concentrated, and separated by column chromatography to obtain 14.8 g of Compound I2-7c (yield 61%).

[0206] (2) Compound 2-7

[0207] [Reaction Equation 9-2]

[0208]

[0209] 6.1 g (12.5 mmol) of Compound I2-7c and 60 mL of tert-butylbenzene were added to a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78 °C. After the addition, the mixture was stirred at 60 °C for 3 hours. Subsequently, nitrogen was blown at 60 °C to remove heptane. 6.3 g (25 mmol) of boron tribromide was added dropwise at -78 °C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was added dropwise at 0 °C. After the addition, the mixture was stirred at 120 °C for 2 hours. After the reaction was complete, an aqueous sodium acetate solution was added at room temperature and stirred. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.0 g of Compound I2-7 (yield 17%).

[0210] 10. Synthesis of Compound 2-9

[0211] (1) Compound I2-9c

[0212] [Reaction Equation 10-1]

[0213]

[0214] 8.4 g (50 mmol) of Compound I2-9a, 21.5 g (50 mmol) of Compound I2-9b, 0.45 g (2 mmol) of Palladium Acetate, 18.9 g (196 mmol) of Sodium Tertiary Butoxide, 0.8 g (4 mmol) of Tritertiary Butylphosphine, and 300 mL of Toluene were added to a 500 mL reactor and stirred under reflux for 5 hours. After the reaction was complete, the mixture was filtered, the filtrate was concentrated, and separated by column chromatography to obtain 15.2 g of Compound I2-9c (yield 54%).

[0215] (2) Compound 2-9

[0216] [Reaction Equation 10-2]

[0217]

[0218] 7.0 g (12.5 mmol) of Compound I2-9c and 60 mL of tert-butylbenzene were added to a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78 °C. After the addition, the mixture was stirred at 60 °C for 3 hours. Subsequently, nitrogen was blown at 60 °C to remove heptane. 6.3 g (25 mmol) of boron tribromide was added dropwise at -78 °C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was added dropwise at 0 °C. After the addition, the mixture was stirred at 120 °C for 2 hours. After the reaction was complete, an aqueous sodium acetate solution was added at room temperature and stirred. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.1 g of Compound I2-9 (yield 16%).

[0219] 11. Synthesis of Compound 2-10

[0220] (1) Compound I2-10c

[0221] [Reaction Equation 11-1]

[0222]

[0223] 8.4 g (98 mmol) of Compound I2-10a, 22.2 g (98 mmol) of Compound I2-10b, 0.45 g (2 mmol) of Palladium Acetate, 18.9 g (196 mmol) of Sodium Tertiary Butoxide, 0.8 g (4 mmol) of Tritertiary Butylphosphine, and 300 mL of Toluene were added to a 500 mL reactor and stirred under reflux for 5 hours. After the reaction was complete, the mixture was filtered, the filtrate was concentrated, and separated by column chromatography to obtain 16.4 g of Compound I2-10c (yield 57%).

[0224] (2) Compound 2-10

[0225] [Reaction Equation 11-2]

[0226]

[0227] 7.2 g (12.5 mmol) of Compound I2-10c and 60 mL of tert-butylbenzene were added to a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78 °C. After the addition, the mixture was stirred at 60 °C for 3 hours. Subsequently, nitrogen was blown at 60 °C to remove heptane. 6.3 g (25 mmol) of boron tribromide was added dropwise at -78 °C. After the addition, the mixture was stirred at room temperature for 1 hour, and 3.2 g (25 mmol) of N,N-diisopropylethylamine was added dropwise at 0 °C. After the addition, the mixture was stirred at 120 °C for 2 hours. After the reaction was complete, an aqueous sodium acetate solution was added at room temperature and stirred. The mixture was extracted with ethyl acetate, the organic layer was concentrated, and separated by column chromatography to obtain 1.2 g of Compound I2-10 (yield 18%).

[0229] In the light-emitting material layer (240), the first compound (242) is used as a dopant (light-emitting body) and can emit blue light.

[0230] Additionally, the light-emitting material layer (240) may further include a second compound (244) used as a host. In this case, the first compound (242) in the light-emitting material layer (240) may have an amount of 0.1 to 30 wt%, preferably 0.1 to 10 wt%, more preferably 1 to 5 wt%. The light-emitting material layer (240) may have a thickness of 10 to 500 Å, preferably 50 to 400 Å, more preferably 100 to 300 Å.

[0231] The second compound (244) that is the host may be an anthracene derivative. For example, the second compound (244) may be represented by Chemical Formula 4.

[0232] [Chemical Formula 4]

[0233]

[0234] In Chemical Formula 4, Ar1 and Ar2 are each independently C6-C 30 aryl group or C5-C 30It is a heteroaryl group, and L is a single bond or C6-C 20 It is an arylene group. In this case, hydrogen may not be substituted, or may be partially or entirely replaced by deuterium.

[0235] In Chemical Formula 4, Ar1 and Ar2 can each be selected from phenyl, naphthyl, dibenzofuranyl, and condensed dibenzofuranyl, and L can be a single bond or phenylene.

[0236] For example, Ar1 can be selected from naphthyl, dibenzofuranyl, phenyldibenzofuranyl, and condensed dibenzofuranyl, and Ar2 can be selected from phenyl and naphthyl. Additionally, both Ar1 and Ar2 may be naphthyl and L may be a single bond or phenylene.

[0237] Additionally, some or all of the hydrogens in the anthracene core may be replaced with deuterium, or some or all of the hydrogens in Ar1, Ar2, and L may be replaced with deuterium. Alternatively, some or all of the hydrogens in the anthracene core, Ar1, Ar2, and L may be replaced with deuterium.

[0238] The second compound (244) shown in Chemical Formula 4 may be one of the compounds of Chemical Formula 5 below.

[0239] [Chemical Formula 5]

[0240]

[0241]

[0242]

[0243]

[0244] The hole injection layer 210 is 4,4',4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4"-tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4',4"-tris(N-(naphthalene-1-yl)-N-phenyl-amino)triphenylamine(1T-NATA), 4,4',4"-tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine(2T-NATA), copper phthalocyanine(CuPc), tris(4-carbazoyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4"-diamine (NPB; NPD), It may include at least one compound selected from 1,4,5,8,9,11-hexaazactriphenylenehexacarbonitrile (dipyrazino[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile; HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiphene)polystyrene sulfonate (PEDOT / PSS), and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine. Alternatively, the hole injection layer (210) may include the following compound of Formula 12 (host) and the following compound of Formula 13 (dopant).

[0245] The hole transport layer 220 is N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine; TPD), NPB (NPD), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl(CBP), poly[N,N'-bis(4-butylpnehyl)-N,N'-bis(phenyl)-benzidine](Poly-TPD), (poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphenylamine))] (TFB), di-[4-(N,N-di-p-tolyl-amino)-phenyl]cyclohexane(TAPC), 3,5-di(9H-carbazol-9-yl)-N,N-diphenylaniline (DCDPA), It may include at least one compound selected from N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine and N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl-4-amine. Alternatively, the hole transport layer (220) may be composed of the following chemical formula 12 compound.

[0246] The electron blocking layer (230), which is positioned between the hole transport layer (220) and the light-emitting material layer (240) to block electron movement from the light-emitting material layer (240) to the hole transport layer (220), includes an electron blocking material (232) which is an amine derivative. For example, the electron blocking material (232) of the electron blocking layer (230) can be represented by the following chemical formula 6.

[0247] [Chemical Formula 6]

[0248]

[0249] In Chemical Formula 6, L is a C6–C30 arylene group, and a is 0 or 1. Also, R1 and R2 are each independently a C6–C30 aryl group or a C5–C30 heteroaryl group.

[0250] For example, L can be phenylene, and R1 and R2 can each independently be biphenyl, fluorenyl, phenylcarbazoyl, carbazoylphenyl, dibenzothiophenyl, or dibenzofuranyl.

[0251] That is, the electron blocking material (232) may be an amine derivative substituted with a spirofluorene group.

[0252] The electron blocking material (232) of Chemical Formula 6 may be one of the compounds of Chemical Formula 7 below.

[0253] [Chemical Formula 7]

[0254]

[0255]

[0256]

[0257]

[0258] Additionally, a hole blocking layer (250) located between the light-emitting material layer (240) and the electron injection layer (260) to prevent hole movement from the light-emitting material layer (240) to the electron injection layer (260) comprises a hole blocking material (252). For example, the hole blocking material (252) may be an azine derivative represented by the chemical formula 8.

[0259] [Chemical Formula 8]

[0260]

[0261] In Chemical Formula 8, Y1 to Y5 are each independently CR1 or N, and one to three of them are N. In this case, R1 is independently a C6 to C30 aryl group. Also, L is a C6 to C30 allylene group, R2 is a C6 to C30 aryl group or a C5 to C30 heteroaryl group, and R3 is a hydrogen or two adjacent ones form a condensed ring. Also, a is 0 or 1, b is 1 or 2, and c is an integer from 0 to 4.

[0262] The hole blocking substance (252) of chemical formula 8 may be one of the compounds of chemical formula 9 below.

[0263] [Chemical Formula 9]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271] In contrast, the hole blocking material (252) of the hole blocking layer (250) may be a benzimidazole derivative represented by the chemical formula 10.

[0272] [Chemical Formula 10]

[0273]

[0274] In chemical formula 10, Ar is a C10-C30 arylene group, R1 is a C6-C30 aryl group or a C5-C30 heteroaryl group, and R2 is hydrogen, a C1-C10 alkyl group or a C6-C30 aryl group.

[0275] For example, Ar can be naphthylene or anthracenylene, R1 can be benzimidazoyl or phenyl, and R2 can be methyl, ethyl, or phenyl.

[0276] The hole-blocking substance (252) of chemical formula 10 may be one of the compounds of chemical formula 11.

[0277] [Chemical Formula 11]

[0278]

[0279]

[0280] The hole blocking material (252) of the hole blocking layer (250) may include one of the compound of Formula 8 and the compound of Formula 10.

[0281] In this case, the thickness of the light-emitting material layer (240) may be greater than the thickness of the electron blocking layer (230) and the hole blocking layer (250), respectively, and smaller than the thickness of the hole transport layer (220). For example, the light-emitting material layer (240) may have a thickness of about 150 to 250 Å, the electron blocking layer (230) and the hole blocking layer (250) may each have a thickness of about 50 to 150 Å, and the hole transport layer (220) may have a thickness of about 900 to 1100 Å. The electron blocking layer (230) and the hole blocking layer (250) may have the same thickness.

[0282] Meanwhile, the hole blocking layer (250) may include both the compound of Formula 8 and the compound of Formula 10 as hole blocking materials (252). For example, in the hole blocking layer (250), the hole blocking material of Formula 8 and the hole blocking material of Formula 10 may have the same weight ratio.

[0283] In this case, the thickness of the light-emitting material layer (240) may be greater than the thickness of the electron blocking layer (230) and smaller than the thickness of the hole blocking layer (250). Additionally, the thickness of the hole blocking layer (250) may be smaller than the thickness of the hole transport layer (220). For example, the light-emitting material layer (240) may have a thickness of about 200 to 300 Å, and the electron blocking layer (230) may have a thickness of about 50 to 150 Å. Additionally, each of the hole blocking layer (250) may have a thickness of about 250 to 350 Å, and the hole transport layer (220) may have a thickness of about 800 to 1000 Å. The electron blocking layer (230) and the hole blocking layer (250) may have the same thickness.

[0284] The compound of Formula 8 and / or Formula 10 (hole blocking material) has electron transport properties, so the electron transport layer can be omitted, and accordingly, the hole blocking layer (250) can come into direct contact with the electron injection layer (260) or the second electrode (164).

[0285] The electron injection layer (260) may include at least one of an alkali metal such as Li, an alkali halide material such as LiF, CsF, NaF, BaF2, and / or an organometallic material such as LiQ, lithium benzoate, sodium stearate, but is not limited thereto. Alternatively, the electron injection layer (260) may include a compound of Formula 14 (host) and an alkali metal (dopant).

[0286] In the organic light-emitting diode (D) of the present invention, the light-emitting material layer (240) comprises a light-emitting compound (242) of Formula 1, and accordingly, the lifespan of the organic light-emitting diode (D) and the organic light-emitting display device (100) is greatly improved.

[0288] [Organic Light Emitting Diode]

[0289] An organic light-emitting diode was fabricated by sequentially stacking an anode (ITO, 0.5 mm), a hole injection layer (Formula 12 (97 wt%) + Formula 13 (3 wt%), 100 Å), a hole transport layer (Formula 12, 1000 Å), an electron blocking layer (Compound EBL-11 of Formula 7, 100 Å), a light-emitting material layer (Host (Compound H-1 of Formula 5, 98 wt%) + Dopant (2 wt%), 200 Å), a hole blocking layer (Compound E1 of Formula 9, 100 Å), an electron injection layer (Formula 14 (98 wt%) + Li (2 wt%), 200 Å), and a cathode (Al, 500 Å), and forming an encapsulation film using UV-cured epoxy and a moisture getter.

[0290] [Chemical Formula 12]

[0291]

[0292] [Chemical Formula 13]

[0293]

[0294] [Chemical Formula 14]

[0295]

[0296] (1) Comparative Example 1 and Comparative Example 2 (Ref1~Ref2)

[0297] A luminescent material layer was formed using the compound of Chemical Formula 15 (Ref-1) and the compound of Chemical Formula 16 (Ref-2), respectively, as dopants.

[0298] (2) Experimental Examples 1 to 11 (Ex1~Ex11)

[0299] A luminescent material layer was formed using compounds 1-1, 1-3, 1-4, 1-6, 1-7, 2-2, 2-3, 2-5, 2-7, 2-9, and 2-10 of Chemical Formula 3, respectively, as dopants.

[0300] [Chemical Formula 15]

[0301]

[0302] [Chemical Formula 16]

[0303]

[0304] The characteristics (driving voltage (V), external quantum efficiency (EQE), color coordinates, and lifetime (T95)) of the organic light-emitting diodes fabricated in Comparative Examples 1 and 2 and Experimental Examples 1 to 11 were measured and are listed in Table 1. The characteristics of the organic light-emitting diodes were measured at room temperature using a current source (KEITHLEY) and a PR 650 photometer. The driving voltage, external quantum efficiency, and color coordinates were 10 mA / cm². 2 It was measured under current density conditions, and the lifetime was 22.5 mA / cm² at 40℃. 2 The time required to reach 95% of the lifespan was measured under the conditions.

[0305] [Table 1]

[0306]

[0307] As shown in Table 1, compared to the organic light-emitting diodes of Comparative Examples 1 and 2, the lifespan of the organic light-emitting diodes of Experimental Examples 1 to 11, which use the light-emitting compound of the present invention as a dopant, is significantly improved.

[0309] FIG. 4 is a schematic cross-sectional view of a double-stack structured organic light-emitting diode used in an organic light-emitting display device according to the first embodiment of the present invention.

[0310] As illustrated in FIG. 4, the organic light-emitting diode (D) comprises first and second electrodes (160, 164) facing each other and an organic light-emitting layer (162) located between the first and second electrodes (160, 164), wherein the organic light-emitting layer (162) comprises a first light-emitting part (310) comprising a first light-emitting material layer (320), a second light-emitting part (330) comprising a second light-emitting material layer (340), and a charge-generating layer (350) located between the first light-emitting part (310) and the second light-emitting part (330). The organic light-emitting display device (100 of FIG. 2) comprises a red pixel, a green pixel, and a blue pixel, and the organic light-emitting diode (D) may be located in the blue pixel.

[0311] One of the first electrode (160) and the second electrode (164) may be an anode, and the other of the first electrode (160) and the second electrode (164) may be a cathode. Additionally, one of the first electrode (160) and the second electrode (164) may be a transmissive electrode (semitransmissive electrode), and the other of the first electrode (160) and the second electrode (164) may be a reflective electrode.

[0312] The charge generating layer (350) is located between the first and second light-emitting parts (310, 330), and the first light-emitting part (310), the charge generating layer (350), and the second light-emitting part (330) are sequentially stacked on the first electrode (160). That is, the first light-emitting part (310) is located between the first electrode (160) and the charge generating layer (350), and the second light-emitting part (330) is located between the second electrode (164) and the charge generating layer (350).

[0313] The first light-emitting part (310) includes a first light-emitting material layer (320). Additionally, the first light-emitting part (310) may further include a first electron blocking layer (316) located between the first electrode (160) and the first light-emitting material layer (320), and a first hole blocking layer (318) located between the first light-emitting material layer (320) and the charge generating layer (350).

[0314] Additionally, the first light-emitting part (310) may further include a first hole transport layer (314) located between the first electrode (160) and the first electron blocking layer (316), and a hole injection layer (312) located between the first electrode (160) and the first hole transport layer (314).

[0315] The first light-emitting material layer (320) contains a light-emitting compound indicated in Chemical Formula 1 as the first compound (322) and emits blue light. For example, the first compound (322) of the first light-emitting material layer (320) may be one of the compounds of Chemical Formula 3.

[0316] The first light-emitting material layer (320) may further include a second compound (324). For example, the second compound (324) may be represented by Chemical Formula 4 and be one of the compounds of Chemical Formula 5.

[0317] At this time, in the first light-emitting material layer (320), the first compound (322) has a smaller weight ratio than the second compound (324), and the first compound (322) can be used as a dopant (light-emitting body) and the second compound (324) can be used as a host. For example, in the first light-emitting material layer (320), the first compound (322) has 0.1 to 30 weight%. To achieve sufficient efficiency and lifespan, the first compound (322) can have about 0.1 to 10 weight%, preferably about 1 to 5 weight%.

[0318] The first electron blocking layer (316) may include a compound indicated by Formula 6 as an electron blocking material. Additionally, the first hole blocking layer (318) may include at least one of the compound of Formula 8 and the compound of Formula 10 as a hole blocking material.

[0319] The second light-emitting part (330) includes a second light-emitting material layer (340). Additionally, the second light-emitting part (330) may further include a second electron blocking layer (334) located between the charge generating layer (350) and the second light-emitting material layer (340), and a second hole blocking layer (336) located between the second light-emitting material layer (340) and the second electrode (164).

[0320] Additionally, the second light-emitting part (330) may further include a second hole transport layer (332) located between the charge generating layer (350) and the second electron blocking layer (334), and an electron injection layer (338) located between the second hole blocking layer (336) and the second electrode (164).

[0321] The second light-emitting material layer (340) contains the light-emitting compound indicated in Chemical Formula 1 as the third compound (342) and emits blue light. For example, the third compound (342) of the first light-emitting material layer (340) may be one of the compounds of Chemical Formula 3.

[0322] The second light-emitting material layer (340) may further include a fourth compound (344). For example, the fourth compound (344) may be represented by Chemical Formula 4 and may be one of the compounds of Chemical Formula 5.

[0323] At this time, in the second light-emitting material layer (340), the third compound (342) has a smaller weight ratio than the fourth compound (344), and the third compound (342) can be used as a dopant (light-emitting body) and the fourth compound (344) can be used as a host. For example, in the second light-emitting material layer (340), the third compound (342) has 0.1 to 30 weight%. To achieve sufficient efficiency and lifespan, the third compound (342) can have about 0.1 to 10 weight%, preferably about 1 to 5 weight%.

[0324] The third compound (342) of the second emitting material (340) may be the same as or different from the first compound (322) of the first emitting material layer (320), and the fourth compound (344) of the second emitting material (340) may be the same as or different from the second compound (324) of the first emitting material layer (320). Additionally, the weight ratio of the first compound (322) in the first emitting material layer (320) and the weight ratio of the third compound (342) in the second emitting material layer (340) may be the same or different.

[0325] The second electron blocking layer (334) may include a compound indicated by Formula 6 as an electron blocking material. Additionally, the second hole blocking layer (336) may include at least one of the compound of Formula 8 and the compound of Formula 10 as a hole blocking material.

[0326] The charge generating layer (350) is located between the first light-emitting part (310) and the second light-emitting part (330). That is, the first light-emitting part (310) and the second light-emitting part (330) are connected by the charge generating layer (350). The charge generating layer (350) may be a PN junction charge generating layer in which an N-type charge generating layer (352) and a P-type charge generating layer (354) are joined.

[0327] The N-type charge generation layer (352) is located between the first electron blocking layer (318) and the second hole transport layer (332), and the P-type charge generation layer (354) is located between the N-type charge generation layer (352) and the second hole transport layer (332).

[0328] In such an organic light-emitting diode (D), each of the first and second light-emitting material layers (320, 340) contains a light-emitting compound (242) of Formula 1, and accordingly, the lifespan of the organic light-emitting diode (D) and the organic light-emitting display device (100) is greatly improved.

[0329] Furthermore, by stacking the blue light-emitting part in a double stack structure, a high color temperature image can be realized in the organic light-emitting display device (100).

[0331] FIG. 5 is a schematic cross-sectional view of an organic light-emitting display device according to a second embodiment of the present invention, and FIG. 6 is a schematic cross-sectional view of a double-stack structured organic light-emitting diode used in an organic light-emitting display device according to a second embodiment of the present invention. In addition, FIG. 7 is a schematic cross-sectional view of a triple-stack structured organic light-emitting diode used in an organic light-emitting display device according to a second embodiment of the present invention.

[0332] As illustrated in FIG. 5, the organic light-emitting display device (400) includes a first substrate (410) in which a red pixel (RP), a green pixel (GP), and a blue pixel (BP) are defined, a second substrate (470) facing the first substrate (410), an organic light-emitting diode (D) located between the first substrate (410) and the second substrate (470) and emitting white light, and a color filter layer (480) located between the organic light-emitting diode (D) and the second substrate (470).

[0333] Each of the first substrate (410) and the second substrate (470) may be a glass substrate or a flexible substrate. For example, the flexible substrate may be any one of a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylenenaphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate, and a polycarbonate (PC) substrate.

[0334] A buffer layer (420) is formed on the first substrate (410), and a thin-film transistor (Tr) is formed on the buffer layer (420) corresponding to each of the red pixel (RP), green pixel (GP), and blue pixel (BP). The buffer layer (420) may be omitted.

[0335] A semiconductor layer (422) is formed on the buffer layer (420). The semiconductor layer (422) may be made of an oxide semiconductor material or polycrystalline silicon.

[0336] A gate insulating film (424) made of an insulating material is formed on the upper surface of the semiconductor layer (422). The gate insulating film (424) may be made of an inorganic insulating material such as silicon oxide or silicon nitride.

[0337] A gate electrode (430) made of a conductive material such as metal is formed on the upper part of the gate insulating film (424) in correspondence with the center of the semiconductor layer (422).

[0338] An interlayer insulating film (432) made of an insulating material is formed on the upper part of the gate electrode (430). The interlayer insulating film (432) may be formed of an inorganic insulating material such as silicon oxide or silicon nitride, or may be formed of an organic insulating material such as benzocyclobutene or photoacryl.

[0339] The interlayer insulating film (432) has first and second contact holes (434, 436) that expose both sides of the semiconductor layer (422). The first and second contact holes (434, 436) are located on both sides of the gate electrode (430) and spaced apart from the gate electrode (430).

[0340] On the interlayer insulating film (432), a source electrode (440) and a drain electrode (442) made of a conductive material such as metal are formed.

[0341] The source electrode (440) and the drain electrode (442) are spaced apart from the gate electrode (430) and contact both sides of the semiconductor layer (422) through the first and second contact holes (434, 436), respectively.

[0342] The semiconductor layer (422), the gate electrode (430), the source electrode (440), and the drain electrode (442) form the thin-film transistor (Tr), and the thin-film transistor (Tr) functions as a driving element.

[0343] Although not illustrated, gate wiring and data wiring intersect to define a pixel, and switching elements connected to the gate wiring and data wiring are further formed. The switching elements are connected to thin-film transistors (Tr), which are driving elements.

[0344] In addition, power wiring is formed spaced apart from data wiring or parallel to data wiring, and a storage capacitor may be further configured to maintain a constant voltage of the gate electrode of a thin-film transistor (Tr), which is a driving element, during one frame.

[0345] A protective layer (450) having a drain contact hole (452) that exposes the drain electrode (442) of the thin-film transistor (Tr) is formed to cover the thin-film transistor (Tr).

[0346] On the protective layer (450), a first electrode (460) connected to the drain electrode (442) of the thin-film transistor (Tr) through the drain contact hole (452) is formed separately for each pixel area. The first electrode (460) may be an anode and may be made of a conductive material with a relatively large work function value, for example, a transparent conductive oxide (TCO). Specifically, the first electrode (460) may be made of indium-tin-oxide (ITO), indium-zinc-oxide (IZO), indium-tin-zinc-oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium-copper-oxide (ICO), and aluminum:zinc oxide (Al:ZnO; AZO).

[0347] In the case where the organic light-emitting display device (400) of the present invention is of the bottom-emission type, the first electrode (460) may have a single-layer structure made of a transparent conductive oxide. Alternatively, in the case where the organic light-emitting display device (400) of the present invention is of the top-emission type, a reflective electrode or a reflective layer may be further formed below the first electrode (460). For example, the reflective electrode or the reflective layer may be made of silver (Ag) or an aluminum-palladium-copper (APC) alloy. In the top-emission type organic light-emitting display device (400), the first electrode (460) may have a triple-layer structure of ITO / Ag / ITO or ITO / APC / ITO.

[0348] A bank layer (466) covering the edge of the first electrode (460) is formed on the protective layer (450). The bank layer (466) exposes the center of the first electrode (460) corresponding to the red, green, and blue pixels (Rp, GP, BP). Since the organic light-emitting diode (D) emits white light from the red, green, and blue pixels (Rp, GP, BP), the light-emitting layer (462) can be formed as a common layer without needing to be separated from the red, green, and blue pixels (Rp, GP, BP). The bank layer (466) is formed to prevent current leakage at the edge of the first electrode (460), and the bank layer (466) may be omitted.

[0349] An organic light-emitting layer (462) is formed on the first electrode (460).

[0350] Referring to FIG. 6, the organic light-emitting layer (462) includes a first light-emitting part (710) including a first light-emitting material layer (720), a second light-emitting part (730) including a second light-emitting material layer (740), and a charge-generating layer (750) located between the first light-emitting part (710) and the second light-emitting part (730).

[0351] The charge generating layer (750) is located between the first and second light-emitting parts (710, 730), and the first light-emitting part (710), the charge generating layer (750), and the second light-emitting part (730) are sequentially stacked on the first electrode (460). That is, the first light-emitting part (710) is located between the first electrode (460) and the charge generating layer (750), and the second light-emitting part (730) is located between the second electrode (464) and the charge generating layer (750).

[0352] The first light-emitting part (710) includes a first light-emitting material layer (720). Additionally, the first light-emitting part (710) may further include a first electron blocking layer (716) located between the first electrode (460) and the first light-emitting material layer (720), and a first hole blocking layer (718) located between the first light-emitting material layer (720) and the charge generating layer (750).

[0353] Additionally, the first light-emitting part (710) may further include a first hole transport layer (714) located between the first electrode (460) and the first electron blocking layer (716), and a hole injection layer (712) located between the first electrode (460) and the first hole transport layer (714).

[0354] At this time, the first light-emitting material layer (720) contains the light-emitting compound indicated in Chemical Formula 1 as the first compound (722) and emits blue light. For example, the first compound (722) of the first light-emitting material layer (720) may be one of the compounds of Chemical Formula 3.

[0355] The first light-emitting material layer (720) may further include a second compound (724). For example, the second compound (724) may be represented by Chemical Formula 4 and be one of the compounds of Chemical Formula 5.

[0356] At this time, in the first light-emitting material layer (720), the first compound (722) has a smaller weight ratio than the second compound (724), and the first compound (722) can be used as a dopant (light-emitting body) and the second compound (724) can be used as a host. For example, in the first light-emitting material layer (720), the first compound (722) has 0.1 to 30 weight%. To achieve sufficient efficiency and lifespan, the first compound (722) can have about 0.1 to 10 weight%, preferably about 1 to 5 weight%.

[0357] The first electron blocking layer (716) may include a compound indicated by Formula 6 as an electron blocking material. Additionally, the first hole blocking layer (718) may include at least one of the compound of Formula 8 and the compound of Formula 10 as a hole blocking material.

[0358] The second light-emitting part (730) includes a second light-emitting material layer (740). Additionally, the second light-emitting part (730) may further include a second electron blocking layer (734) located between the charge generating layer (750) and the second light-emitting material layer (740), and a second hole blocking layer (736) located between the second light-emitting material layer (740) and the second electrode (464).

[0359] Additionally, the second light-emitting part (730) may further include a second hole transport layer (732) located between the charge generating layer (750) and the second electron blocking layer (734), and an electron injection layer (738) located between the second hole blocking layer (736) and the second electrode (464).

[0360] The second light-emitting material layer (740) may be a yellow-green light-emitting material layer. For example, the second light-emitting material layer (740) may include a yellow-green dopant (743) and a host (745). For example, the yellow-green dopant (743) may be one of a yellow-green fluorescent compound, a yellow-green phosphorescent compound, or a yellow-green delayed fluorescent compound.

[0361] In the second light-emitting material layer (740), the host (745) has about 70 to 99.9 weight%, and the yellow-green dopant (743) has about 0.1 to 30 weight%. To achieve sufficient efficiency and lifespan, the yellow-green dopant (743) may have about 0.1 to 10 weight%, preferably about 1 to 5 weight%.

[0362] The second electron blocking layer (734) may include a compound indicated by Formula 6 as an electron blocking material. Additionally, the second hole blocking layer (736) may include at least one of the compound of Formula 8 and the compound of Formula 10 as a hole blocking material.

[0363] The charge generating layer (750) is located between the first light-emitting part (710) and the second light-emitting part (730). That is, the first light-emitting part (710) and the second light-emitting part (730) are connected by the charge generating layer (750). The charge generating layer (750) may be a PN junction charge generating layer in which an N-type charge generating layer (752) and a P-type charge generating layer (754) are joined.

[0364] The N-type charge generation layer (752) is located between the first electron blocking layer (718) and the second hole transport layer (732), and the P-type charge generation layer (754) is located between the N-type charge generation layer (752) and the second hole transport layer (732).

[0365] In FIG. 6, a first emitting material layer (720) located between the first electrode (460) and the charge generation layer (750) is shown to include a first compound (722) which is a emitting compound of the present invention and a second compound (724) which is an anthracene derivative, and a second emitting material layer (740) located between the second electrode (764) and the charge generation layer (750) is shown to be a yellow-green emitting material layer. Alternatively, the first emitting material layer (720) located between the first electrode (460) and the charge generation layer (750) may be a yellow-green emitting material layer, and the second emitting material layer (740) located between the second electrode (764) and the charge generation layer (750) may be a blue emitting material layer containing a emitting compound of the present invention and an anthracene derivative.

[0366] In such an organic light-emitting diode (D), the first light-emitting material layer (720) includes a light-emitting compound (242) of chemical formula 1, and accordingly, the lifespan of the organic light-emitting diode (D) and the organic light-emitting display device (100) is greatly improved.

[0367] In addition, an organic light-emitting diode (D) equipped with a first light-emitting part (710) that emits blue light and a second light-emitting part (730) that emits yellow-green light can emit white light.

[0368] Referring to FIG. 7, the organic light-emitting layer (462) includes a first light-emitting part (530) including a first light-emitting material layer (520), a second light-emitting part (550) including a second light-emitting material layer (540), a third light-emitting part (570) including a third light-emitting material layer (560), a first charge-generating layer (580) located between the first light-emitting part (530) and the second light-emitting part (550), and a second charge-generating layer (590) located between the second light-emitting part (550) and the third light-emitting part (570).

[0369] The first charge generating layer (580) is located between the first and second light-emitting parts (530, 550), and the second charge generating layer (590) is located between the second and third light-emitting parts (550, 570). That is, the first light-emitting part (530), the first charge generating layer (580), the second light-emitting part (550), the second charge generating layer (590), and the third light-emitting part (570) are sequentially stacked on the first electrode (460). That is, the first light-emitting part (530) is located between the first electrode (460) and the first charge generating layer (580), the second light-emitting part (550) is located between the first and second charge generating layers (580, 590), and the third light-emitting part (570) is located between the second charge generating layer (590) and the second electrode (464).

[0370] The first light-emitting part (530) may include a hole injection layer (532), a first hole transport layer (534), a first electron blocking layer (536), a first light-emitting material layer (520), and a first hole blocking layer (538) that are sequentially stacked on the first electrode (460). For example, the hole injection layer (532), the first hole transport layer (534), and the first electron blocking layer (536) may be sequentially located between the first electrode (460) and the first light-emitting material layer (520), and the first hole blocking layer (538) may be located between the first light-emitting material layer (520) and the first charge generation layer (580).

[0371] The first light-emitting material layer (520) contains a light-emitting compound indicated in Chemical Formula 1 as the first compound (522) and emits blue light. For example, the first compound (522) of the first light-emitting material layer (520) may be one of the compounds of Chemical Formula 3.

[0372] The first light-emitting material layer (520) may further include a second compound (524). For example, the second compound (524) may be represented by Chemical Formula 4 and be one of the compounds of Chemical Formula 5.

[0373] At this time, in the first light-emitting material layer (520), the first compound (522) has a smaller weight ratio than the second compound (524), and the first compound (522) can be used as a dopant (light-emitting body) and the second compound (524) can be used as a host. For example, in the first light-emitting material layer (520), the first compound (522) has 0.1 to 30 weight%. To achieve sufficient efficiency and lifespan, the first compound (522) can have about 0.1 to 10 weight%, preferably about 1 to 5 weight%.

[0374] The first electron blocking layer (536) may include a compound indicated by Formula 6 as an electron blocking material. Additionally, the first hole blocking layer (538) may include at least one of the compound of Formula 8 and the compound of Formula 10 as a hole blocking material.

[0375] The second light-emitting part (550) may include a second hole transport layer (552), a second light-emitting material layer (540), and an electron transport layer (554). The second hole transport layer (552) is located between the first charge generating layer (580) and the second light-emitting material layer (540), and the electron transport layer (554) is located between the second light-emitting material layer (540) and the second charge generating layer (590).

[0376] The second light-emitting material layer (540) may be a yellow-green light-emitting material layer. For example, the second light-emitting material layer (540) may include a host and a yellow-green dopant.

[0377] The second light-emitting material layer (540) may include a host, a red dopant, and a green dopant. In this case, the second light-emitting material layer (540) may have a single-layer structure or a double-layer structure consisting of a lower layer including a host and a red dopant (or green dopant) and an upper layer including a host and a green dopant (or red dopant).

[0378] Additionally, the second light-emitting material layer (540) may have a triple-layer structure comprising a first layer containing a host and a red dopant, a second layer containing a host and a yellow-green dopant, and a third layer containing a host and a green dopant.

[0379] The third light-emitting part (570) may include a third hole transport layer (572), a second electron blocking layer (574), a third light-emitting material layer (560), a second hole blocking layer (576), and an electron injection layer (578).

[0380] The third light-emitting material layer (560) contains the light-emitting compound indicated in Chemical Formula 1 as the third compound (562) and emits blue light. For example, the third compound (562) of the third light-emitting material layer (560) may be one of the compounds of Chemical Formula 3.

[0381] The third light-emitting material layer (560) may further include a fourth compound (564). For example, the fourth compound (564) may be represented by Chemical Formula 4 and may be one of the compounds of Chemical Formula 5.

[0382] At this time, in the third light-emitting material layer (560), the third compound (562) has a smaller weight ratio than the fourth compound (564), and the third compound (562) can be used as a dopant (light-emitting body) and the fourth compound (564) can be used as a host. For example, in the third light-emitting material layer (560), the third compound (562) has 0.1 to 30 weight%. To achieve sufficient efficiency and lifespan, the third compound (562) can have about 0.1 to 10 weight%, preferably about 1 to 5 weight%.

[0383] The third compound (562) of the third light-emitting material (560) may be the same as or different from the first compound (522) of the first light-emitting material layer (520), and the fourth compound (564) of the third light-emitting material (560) may be the same as or different from the second compound (524) of the first light-emitting material layer (520). Additionally, the weight ratio of the first compound (522) in the first light-emitting material layer (520) and the weight ratio of the third compound (562) in the third light-emitting material layer (560) may be the same or different.

[0384] The second electron blocking layer (574) may include a compound indicated by Formula 6 as an electron blocking material. Additionally, the second hole blocking layer (576) may include at least one of the compound of Formula 8 and the compound of Formula 10 as a hole blocking material.

[0385] The first charge generating layer (580) is located between the first light-emitting part (530) and the second light-emitting part (550), and the second charge generating layer (590) is located between the second light-emitting part (550) and the third light-emitting part (570). That is, the first light-emitting part (530) and the second light-emitting part (550) are connected by the first charge generating layer (580), and the second light-emitting part (550) and the third light-emitting part (570) are connected by the second charge generating layer (590). The first charge generating layer (580) may be a PN junction charge generating layer in which an N-type charge generating layer (582) and a P-type charge generating layer (584) are joined, and the second charge generating layer (590) may be a PN junction charge generating layer in which an N-type charge generating layer (592) and a P-type charge generating layer (594) are joined.

[0386] In the first charge generation layer (580), the N-type charge generation layer (582) is located between the first hole blocking layer (538) and the second hole transport layer (552), and the P-type charge generation layer (584) is located between the N-type charge generation layer (582) and the second hole transport layer (552).

[0387] In the second charge generation layer (590), the N-type charge generation layer (592) is located between the electron transport layer (454) and the third hole transport layer (572), and the P-type charge generation layer (594) is located between the N-type charge generation layer (592) and the third hole transport layer (572).

[0388] In the organic light-emitting diode (D), the first and third light-emitting material layers (520, 560) each contain a light-emitting compound (242) of Formula 1, and accordingly, the lifespan of the organic light-emitting diode (D) and the organic light-emitting display device (100) is greatly improved.

[0389] Additionally, an organic light-emitting diode (D) equipped with first and third light-emitting parts (530, 570) and a second light-emitting part (550) that emits yellow-green or red / green light can emit white light.

[0390] Meanwhile, in FIG. 7, the organic light-emitting diode (D) has a triple stack structure including a first light-emitting part (530), a second light-emitting part (550), and a third light-emitting part (570). Alternatively, the organic light-emitting diode (D) may include additional light-emitting parts and a charge-generating layer.

[0391] Referring again to FIG. 5, a second electrode (464) is formed on the upper part of the first substrate (410) on which the organic light-emitting layer (462) is formed.

[0392] In the organic light-emitting display device (400) of the present invention, light emitted from the organic light-emitting layer (462) is incident on the color filter layer (480) through the second electrode (464), so the second electrode (464) has a thin thickness so that light can be transmitted.

[0393] The first electrode (460), the organic light-emitting layer (462), and the second electrode (464) form an organic light-emitting diode (D).

[0394] The color filter layer (480) is located on top of the organic light-emitting diode (D) and includes a red color filter (482), a green color filter (484), and a blue color filter (486) corresponding to each of the red pixel (RP), the green pixel (GP), and the blue pixel (BP). The red color filter (482) may include at least one of a red dye and a red pigment, the green color filter (484) may include at least one of a green dye and a green pigment, and the blue color filter (485) may include at least one of a blue dye and a blue pigment.

[0395] Although not illustrated, the color filter layer (480) may be attached to the organic light-emitting diode (D) by an adhesive layer. Alternatively, the color filter layer (480) may be formed directly on the organic light-emitting diode (D).

[0396] Although not shown, an encapsulation film may be formed to prevent external moisture from penetrating into the organic light-emitting diode (D). For example, the encapsulation film may have a laminated structure of a first inorganic insulating layer, an organic insulating layer, and a second inorganic insulating layer, but is not limited thereto.

[0397] Additionally, a polarizing plate may be attached to the outer surface of the second substrate (470) to reduce external light reflection. For example, the polarizing plate may be a circular polarizing plate.

[0398] In the organic light-emitting diode (D) of FIG. 5, the first electrode (460) is a reflective electrode and the second electrode (464) is a transmissive (semi-transmissive) electrode, and the color filter layer (480) is disposed on the upper part of the organic light-emitting diode (D). Alternatively, the first electrode (460) may be a transmissive (semi-transmissive) electrode and the second electrode (464) may be a reflective electrode, in which case the color filter layer (480) may be disposed between the organic light-emitting diode (D) and the first substrate (410).

[0399] Additionally, a color conversion layer (not shown) may be provided between the organic light-emitting diode (D) and the color filter layer (480). The color conversion layer includes a red color conversion layer, a green color conversion layer, and a blue color conversion layer corresponding to each pixel, and can convert white light from the organic light-emitting diode (D) into red, green, and blue, respectively. For example, the color conversion layer may include quantum dots. Thus, the color purity of the organic light-emitting display device (400) can be further improved.

[0400] In addition, a color conversion layer may be included instead of the color filter layer (480).

[0401] As described above, in the organic light-emitting display device (400), the organic light-emitting diodes (D) of the red pixel (RP), green pixel (GP), and blue pixel (BP) emit white light, and the light from the organic light-emitting diodes (D) passes through the red color filter (482), green color filter (484), and blue color filter (486), thereby displaying green, red, and blue colors in the red pixel (RP), green pixel (GP), and blue pixel (BP), respectively.

[0402] Meanwhile, in FIGS. 5 to 7, an organic light-emitting diode (D) that emits white light is used in a display device. Alternatively, the organic light-emitting diode (D) may be formed on the entire surface of a substrate without a driving element such as a thin-film transistor (Tr) and a color filter layer (480) and used in a lighting device. In the present invention, the organic light-emitting device includes a display device and a lighting device.

[0404] FIG. 8 is a schematic cross-sectional view of an organic light-emitting display device according to a third embodiment of the present invention.

[0405] As illustrated in FIG. 8, the organic light-emitting display device (600) includes a first substrate (610) in which a red pixel (RP), a green pixel (GP), and a blue pixel (BP) are defined, a second substrate (670) facing the first substrate (610), an organic light-emitting diode (D) located between the first substrate (610) and the second substrate (670) and emitting blue light, and a color conversion layer (680) located between the organic light-emitting diode (D) and the second substrate (670).

[0406] Although not shown, a color filter may be formed between each of the second substrate (670) and the color conversion layer (680).

[0407] Each of the first substrate (610) and the second substrate (670) may be a glass substrate or a flexible substrate. For example, the flexible substrate may be any one of a polyimide (PI) substrate, a polyethersulfone (PES) substrate, a polyethylenenaphthalate (PEN) substrate, a polyethylene terephthalate (PET) substrate, and a polycarbonate (PC) substrate.

[0408] On the first substrate (610), a thin film transistor (Tr) is provided corresponding to each of the red pixel (RP), green pixel (GP), and blue pixel (BP), and a protective layer (650) is formed covering the thin film transistor (Tr) and having a drain contact hole (652) that exposes one electrode of the thin film transistor (Tr), for example, the drain electrode.

[0409] An organic light-emitting diode (D) comprising a first electrode (660), an organic light-emitting layer (662), and a second electrode (664) is formed on the protective layer (650). At this time, the first electrode (660) can be connected to the drain electrode of a thin-film transistor (Tr) through a drain contact hole (652).

[0410] Additionally, a bank layer (666) covering the edge of the first electrode (660) is formed at the boundary of each of the red pixel (RP), green pixel (GP), and blue pixel (BP). Since the organic light-emitting diode (D) emits blue light from the red pixel (RP), green pixel (GP), and blue pixel (BP), the light-emitting layer (662) can be formed as a common layer without needing to be separated from the red pixel (RP), green pixel (GP), and blue pixel (BP). The bank layer (666) is formed to prevent current leakage at the edge of the first electrode (660), and the bank layer (666) may be omitted.

[0411] At this time, the organic light-emitting diode (D) has the structure of FIG. 3 or FIG. 4 and can emit blue light. That is, the organic light-emitting diode (D) is provided in each of the red pixel (RP), green pixel (GP), and blue pixel (BP) to provide blue light.

[0412] Since the organic light-emitting diode (D) emits blue light from the red pixel (RP), green pixel (GP), and blue pixel (BP), the light-emitting layer (662) can be formed as a common layer without needing to be separated from the red pixel (RP), green pixel (GP), and blue pixel (BP). The bank layer (666) is formed to prevent current leakage at the edge of the first electrode (660), and the bank layer (666) can be omitted.

[0413] The color conversion layer (680) includes a first color conversion layer (682) corresponding to a red pixel (RP) and a second color conversion layer (684) corresponding to a green pixel (BP). For example, the color conversion layer (680) may be made of an inorganic light-emitting material such as a quantum dot. A color conversion layer is not formed on the blue pixel (BP), and the organic light-emitting diode (D) of the blue pixel (BP) may face directly with the second substrate (670).

[0414] Blue light from the organic light-emitting diode (D) in the red pixel (RP) is converted into red light by the first color conversion layer (682), and blue light from the organic light-emitting diode (D) in the green pixel (GP) is converted into green light by the second color conversion layer (684).

[0415] Therefore, the organic light-emitting display device (600) can display a color image.

[0416] Meanwhile, when light from the organic light-emitting diode (D) passes through the first substrate (610) and is displayed, the color conversion layer (680) may be provided between the organic light-emitting diode (D) and the first substrate (610).

[0418] Although the present invention has been described above with reference to preferred embodiments, those skilled in the art will understand that various modifications and changes can be made to the invention without departing from the technical spirit and scope of the invention as described in the following claims. Explanation of the symbols

[0420] 100, 400, 600: Organic light-emitting display device 160, 460, 660: First electrode 162, 462, 662: Organic light-emitting layer 164, 464, 664: Second electrode 240, 320, 340, 520, 540, 560, 720, 740: Luminescent material layer 242, 322, 342, 522, 562, 722: First compound (luminescent agent) D: Organic light-emitting diode

Claims

Claim 1 Represented by Chemical Formula 2-1 or Chemical Formula 2-3, [Chemical Formula 2-1] [Chemical Formula 2-3] In Chemical Formulas 2-1 and 2-3, X is one of B, P=O, P=S, Y1 is one of NR1, C(R2)2, O, S, Se, Si(R3)2, Y2 is O or S, R2 to R6 are each independently selected from hydrogen, deuterium, C1 to C10 alkyl groups unsubstituted or substituted with deuterium, C6 to C30 arylamines substituted unsubstituted or substituted with deuterium or C1 to C10 alkyl groups, C6 to C30 aryl groups substituted unsubstituted or substituted with deuterium or C1 to C10 alkyl groups, C5 to C30 heteroaryl groups substituted unsubstituted or substituted with deuterium or C1 to C10 alkyl groups, and R7, R8, and R9 are each independently selected from hydrogen, deuterium, C1 to C10 alkyl groups substituted unsubstituted or substituted with deuterium, unsubstituted or substituted with deuterium or C1 A C6 to C30 arylamine group substituted with an alkyl group of up to C10, an aryl group of C6 to C30 that is unsubstituted or substituted with deuterium or an alkyl group of C1 to C10, and a C6 to C30 heteroaryl group substituted with an alkyl group of C1 to C10 that is unsubstituted or substituted with deuterium or an alkyl group of C1 to C10, wherein in Formula 2-1, R1 is selected from hydrogen, deuterium, an alkyl group of C1 to C10 that is unsubstituted or substituted with deuterium, an arylamine group of C6 to C30 that is unsubstituted or substituted with a deuterium or an alkyl group of C1 to C10, an aryl group of C6 to C30 substituted with a deuterium or an alkyl group of C1 to C10, and a heteroaryl group of C5 to C30 that is unsubstituted or substituted with a deuterium or an alkyl group of C1 to C10, wherein in Formula 2-3, Z1 to Z4 are each independently N or CR 10 and, one of Z1 to Z4 is N, and R 10 A luminescent compound characterized by being independently selected from hydrogen, deuterium, a C1 to C10 alkyl group that is unsubstituted or substituted with deuterium, a C6 to C30 arylamine group that is unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, a C6 to C30 aryl group that is unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, or a C6 to C30 heteroaryl group that is unsubstituted or substituted with deuterium or a C1 to C10 alkyl group. Claim 2 delete Claim 3 A luminescent compound according to claim 1, characterized in that the above chemical formula 2-1 is represented by chemical formula 2-2.[Chemical formula 2-2] Claim 4 delete Claim 5 A luminescent compound according to claim 1, characterized in that the above chemical formula 2-3 is represented by chemical formula 2-4.[Chemical formula 2-4] Claim 6 A luminescent compound according to claim 1, characterized in that the luminescent compound is one of the compounds of the following chemical formula 3.[Chemical Formula 3] Claim 7 An organic light-emitting device comprising: a substrate; a first electrode; a second electrode facing the first electrode; and an organic light-emitting diode positioned on the substrate, the first electrode comprising a first light-emitting material layer positioned between the first electrode and the second electrode and comprising a first compound, wherein the first compound is a light-emitting compound described in one of claims 1, 3, 5, and 6. Claim 8 In claim 7, the first luminescent material layer further comprises a second compound, said second compound is represented by Chemical Formula 4, wherein Ar1 and Ar2 are each independently C6-C 30 aryl group or C5-C 30 It is a heteroaryl group, and L is a single bond or C6-C 20 An organic light-emitting device characterized by having an arylene group, wherein hydrogen is not substituted or is partially or entirely substituted with deuterium.[Chemical Formula 4] Claim 9 An organic light-emitting diode according to claim 7, wherein the organic light-emitting diode further comprises a second light-emitting material layer located between the first light-emitting material layer and the second electrode and the third compound, and a first charge-generating layer located between the first light-emitting material layer and the second light-emitting material layer, wherein the third compound is represented by Chemical Formula 2-1 or Chemical Formula 2-3. Claim 10 An organic light-emitting device according to claim 7, wherein the substrate has a red pixel, a green pixel, and a blue pixel defined therein, and the organic light-emitting diode corresponds to the red pixel, the green pixel, and the blue pixel, and further comprising a color conversion layer provided between the substrate and the organic light-emitting diode or on top of the organic light-emitting diode corresponding to the red pixel and the green pixel. Claim 11 An organic light-emitting diode according to claim 9, wherein the organic light-emitting diode further comprises a third light-emitting material layer located between the first charge generating layer and the second light-emitting material layer, and a second charge generating layer located between the second light-emitting material layer and the third light-emitting material layer, wherein the third light-emitting material layer emits yellow-green light or emits red and green light. Claim 12 An organic light-emitting device according to claim 7, wherein the organic light-emitting diode further comprises a second light-emitting material layer located between the first light-emitting material layer and the second electrode, and a first charge-generating layer located between the first light-emitting material layer and the second light-emitting material layer, the organic light-emitting diode emitting a yellow-green color. Claim 13 An organic light-emitting device according to claim 11, wherein a red pixel, a green pixel, and a blue pixel are defined on the substrate, and the organic light-emitting diode corresponds to the red pixel, the green pixel, and the blue pixel, and further comprising a color filter layer provided between the substrate and the organic light-emitting diode or on top of the organic light-emitting diode corresponding to the red pixel, the green pixel, and the blue pixel. Claim 14 An organic light-emitting device according to claim 8, wherein the second compound is selected from the compounds of the following chemical formula 5.[Chemical Formula 5]

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