KR20220095098A - Emitting compound and orgnic light emitting device including the same - Google Patents

Abstract

The objective of the present invention is to solve low luminous efficiency and short lifetime, which are problems found in conventional organic light emitting diodes and organic light emitting devices. To this end, the present invention provides a light-emitting compound represented by the following chemical formula, an organic light-emitting diode and organic light-emitting device comprising the same.

Description

EMITTING COMPOUND AND ORGNIC LIGHT EMITTING DEVICE INCLUDING THE SAME

The present invention relates to a light emitting compound, and more particularly, to a light emitting compound having high luminous efficiency and lifetime, and an organic light emitting diode and an organic light emitting device including the same.

Recently, as the display device becomes larger, the demand for a flat display device that occupies less space is increasing. As one of the flat display devices, the technology of an organic light emitting diode (OLED) is rapidly developing.

An organic light emitting diode is a device that emits light when electrons and holes are injected from a cathode and anode into a light emitting material layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), the electrons and holes are paired and then disappear. The device can be formed on a flexible transparent substrate such as plastic, and it can be driven at a low voltage (10V or less), and has the advantage of relatively low power consumption and excellent color.

For example, an organic light emitting diode display includes a red pixel, a green pixel, and a blue pixel, and an organic light emitting diode is formed in each pixel.

However, the blue organic light emitting diode does not realize sufficient luminous efficiency and lifespan, and accordingly, the organic light emitting display device also has limitations in luminous efficiency and lifespan.

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.

In order to solve the above problems, the present invention is represented by Formula 1, n is 0 or 1, X is one of B, P=O, P=S, Y ₁ and Y ₂ Each is independently NR ₁ , C(R ₂ ) ₂ , O, S, Se, Si(R ₃ ) ₂ , Y ₃ is O or S, and R ₁ to R ₃ are each independently hydrogen, deuterium, unsubstituted or deuterium A C1 to C10 alkyl group substituted with a C6 to C30 arylamine group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, a C6 to C30 aryl group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, is selected from a C5 to C30 heteroaryl group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, and each of R ₄ to R ₇ is independently hydrogen, deuterium, an unsubstituted or deuterated C1 to C10 alkyl group, C6 to C30 arylamine group unsubstituted or substituted with deuterium or C1 to C10 alkyl group, C6 to C30 aryl group unsubstituted or substituted with deuterium or C1 to C10 alkyl group, unsubstituted or deuterium or C1 to C10 alkyl group Selected from a C5 to C30 heteroaryl group substituted with an alkyl group or two adjacent ones are connected to each other to form a ring, and R ₈ and R ₉ are each independently hydrogen, deuterium, or a C1 to C10 alkyl group substituted with unsubstituted or deuterium, substituted C6 to C30 arylamine group unsubstituted or substituted with deuterium or C1 to C10 alkyl group, C6 to C30 aryl group unsubstituted or substituted with deuterium or C1 to C10 alkyl group, unsubstituted or deuterium or C1 to C10 alkyl group is selected from a C5 to C30 heteroaryl group substituted with or linked to each other to form a ring, and each of the A ring and the E ring is independently a substituted or unsubstituted 6-membered cycloalkyl ring, a substituted or unsubstituted 6-membered aromatic ring, substituted or unsubstituted heteroaromatic ring It provides a light-emitting compound characterized in that.

[Formula 1]

Formula 1 is characterized in that it is represented by Formula 2-1.

[Formula 2-1]

Formula 2-1 is represented by Formula 2-2, and in Formula 2-2, R ₂₁ to R ₂₇ are each independently hydrogen, deuterium, a C1 to C10 alkyl group unsubstituted or substituted with deuterium, unsubstituted or C6 to C30 arylamine group substituted with deuterium or C1 to C10 alkyl group, C6 to C30 aryl group unsubstituted or substituted with deuterium or C1 to C10 alkyl group, unsubstituted or substituted with deuterium or C1 to C10 alkyl group It is characterized in that it is selected from a C5 to C30 heteroaryl group.

[Formula 2-2]

Formula 1 is characterized in that it is represented by Formula 3-1.

[Formula 3-1]

Formula 3-1 is represented by Formula 3-2, and in Formula 3-2, R ₃₁ to R ₃₇ are each independently hydrogen, deuterium, a C1 to C10 alkyl group unsubstituted or substituted with deuterium, unsubstituted or C6 to C30 arylamine group substituted with deuterium or C1 to C10 alkyl group, C6 to C30 aryl group unsubstituted or substituted with deuterium or C1 to C10 alkyl group, unsubstituted or substituted with deuterium or C1 to C10 alkyl group It is characterized in that it is selected from a C5 to C30 heteroaryl group.

[Formula 3-2]

Formula 3-1 is represented by Formula 3-3, In Formula 3-3, Y ₄ is one of NR ₁ , C(R ₂ ) ₂ , O, S, Se, Si(R ₃ ) ₂ , each of R ₁₀ to R ₁₃ is independently hydrogen, deuterium, a C1 to C10 alkyl group unsubstituted or substituted with deuterium, a C6 to C30 arylamine group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, unsubstituted or selected from a C6 to C30 aryl group substituted with deuterium or a C1 to C10 alkyl group, a C5 to C30 heteroaryl group unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group, or adjacent two are connected to each other to form a ring, R ₁₄ and R ₁₅ are each independently hydrogen, deuterium, a C1 to C10 alkyl group unsubstituted or substituted with deuterium, a C6 to C30 arylamine group which is unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, unsubstituted or deuterium Or a C1 to C10 alkyl group substituted C6 to C30 aryl group, unsubstituted or substituted with a C1 to C10 alkyl group C5 to C30 heteroaryl group substituted with a C5 to C30 heteroaryl group It is characterized in that it is connected to each other to form a ring.

[Formula 3-3]

Formula 3-3 is represented by Formula 3-4, and in Formula 3-4, R ₄₁ to R ₄₃ are each independently hydrogen, deuterium, a C1 to C10 alkyl group unsubstituted or substituted with deuterium, unsubstituted or C6 to C30 arylamine group substituted with deuterium or C1 to C10 alkyl group, C6 to C30 aryl group unsubstituted or substituted with deuterium or C1 to C10 alkyl group, unsubstituted or substituted with deuterium or C1 to C10 alkyl group It is characterized in that it is selected from a C5 to C30 heteroaryl group.

[Formula 3-4]

In another aspect, the present invention, a substrate; a first electrode; a second electrode facing the first electrode; An organic light emitting diode including a first compound and a first light emitting material layer positioned between the first electrode and the second electrode, and an organic light emitting diode positioned on the substrate, wherein the first compound is represented by Formula 1, , in Formula 1, n is 0 or 1, X is one of B, P=O, P=S, and Y ₁ and Y ₂ are each independently NR ₁ , C(R ₂ ) ₂ , O, S, Se, one of Si(R ₃ ) ₂ , Y ₃ is O or S, and R ₁ to R ₃ are each independently hydrogen, deuterium, a C1 to C10 alkyl group unsubstituted or substituted with deuterium, unsubstituted or deuterium or a C1 to C10 arylamine group substituted with a C1 to C10 alkyl group, a C6 to C30 aryl group unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group, unsubstituted or substituted with deuterium or a C1 to C10 alkyl group selected from a C5 to C30 heteroaryl group, each of R ₄ to R ₇ is independently hydrogen, deuterium, an unsubstituted or deuterated C1 to C10 alkyl group, unsubstituted or substituted with deuterium or a C1 to C10 alkyl group Selected from a C6 to C30 arylamine group, a C6 to C30 aryl group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, a C5 to C30 heteroaryl group which is unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group or two adjacent ones are linked to each other to form a ring, and each of R ₈ and R ₉ is independently hydrogen, deuterium, an unsubstituted or deuterium-substituted C1 to C10 alkyl group, unsubstituted or deuterium or C1 to C10 substituted with a C10 alkyl group. a to C30 arylamine group, a C6 to C30 aryl group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, a C5 to C30 heteroaryl group which is unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group, or They are linked to each other to form a ring, and each of Ring A and Ring E is independently It provides an organic light emitting device, characterized in that selected from a substituted or unsubstituted 6-membered cycloalkyl ring, a substituted or unsubstituted 6-membered aromatic ring, and a substituted or unsubstituted heteroaromatic ring.

[Formula 1]

In the organic light emitting device of the present invention, Chemical Formula 1 is represented by Chemical Formula 2-1.

[Formula 2-1]

In the organic light emitting device of the present invention, Formula 2-1 is represented by Formula 2-2, and in Formula 2-2, R ₂₁ to R ₂₇ are each independently hydrogen, deuterium, unsubstituted or substituted with deuterium C1 to C10 alkyl group, unsubstituted or substituted with deuterium or C1 to C10 alkyl group, C6 to C30 arylamine group, unsubstituted or substituted with deuterium or C1 to C10 alkyl group, C6 to C30 aryl group, unsubstituted or substituted with a C1 to C10 alkyl group It is characterized in that it is selected from a C5 to C30 heteroaryl group substituted with deuterium or a C1 to C10 alkyl group.

[Formula 2-2]

In the organic light emitting device of the present invention, Chemical Formula 1 is represented by Chemical Formula 3-1.

[Formula 3-1]

In the organic light emitting device of the present invention, Formula 3-1 is represented by Formula 3-2, and in Formula 3-2, R ₃₁ to R ₃₇ are each independently hydrogen, deuterium, unsubstituted or substituted with deuterium. C1 to C10 alkyl group, unsubstituted or substituted with deuterium or C1 to C10 alkyl group, C6 to C30 arylamine group, unsubstituted or substituted with deuterium or C1 to C10 alkyl group, C6 to C30 aryl group, unsubstituted or substituted with a C1 to C10 alkyl group It is characterized in that it is selected from a C5 to C30 heteroaryl group substituted with deuterium or a C1 to C10 alkyl group.

[Formula 3-2]

In the organic light emitting device of the present invention, Formula 3-1 is represented by Formula 3-3, and in Formula 3-3, Y ₄ is NR ₁ , C(R ₂ ) ₂ , O, S, Se, Si (R ₃ ) is one of ₂ , and each of R ₁₀ to R ₁₃ is independently hydrogen, deuterium, an unsubstituted or deuterated C1 to C10 alkyl group, unsubstituted or deuterium or a C1 to C10 alkyl group substituted with a C6 to C10 alkyl group. A C30 arylamine group, a C6 to C30 aryl group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, a C5 to C30 heteroaryl group which is unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group, or adjacent They are linked to each other to form a ring, and each of R ₁₄ and R ₁₅ is independently hydrogen, deuterium, an unsubstituted or deuterium C1 to C10 alkyl group, unsubstituted or deuterium or a C1 to C10 alkyl group substituted with a C6 to C30 alkyl group. of an arylamine group, a C6 to C30 aryl group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, a C5 to C30 heteroaryl group which is unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group or linked to each other It is characterized in that it forms a ring.

[Formula 3-3]

In the organic light emitting device of the present invention, Chemical Formula 3-3 is represented by Chemical Formula 3-4, and in Chemical Formula 3-4, each of R ₄₁ to R ₄₃ is independently hydrogen, deuterium, unsubstituted or substituted with deuterium. C1 to C10 alkyl group, unsubstituted or substituted with deuterium or C1 to C10 alkyl group, C6 to C30 arylamine group, unsubstituted or substituted with deuterium or C1 to C10 alkyl group, C6 to C30 aryl group, unsubstituted or substituted with a C1 to C10 alkyl group It is characterized in that it is selected from a C5 to C30 heteroaryl group substituted with deuterium or a C1 to C10 alkyl group.

[Formula 3-4]

In the organic light emitting device of the present invention, the first light emitting material layer further comprises a second compound, the second compound is represented by Chemical Formula 5, and in Chemical Formula 4, Ar ₁ and Ar ₂ are each independently C ₆ -C ₃₀ aryl group or C ₅ -C ₃₀ heteroaryl group, L is a single bond or C ₆ -C ₂₀ arylene group, and hydrogen is unsubstituted or some or all of it is substituted with deuterium.

[Formula 5]

In the organic light emitting device of the present invention, the organic light emitting diode comprises: a second light emitting material layer including a third compound and positioned between the first light emitting material layer and the second electrode; It may further include a first charge generating layer positioned between the first light emitting material layer and the second light emitting material layer, wherein the third compound is represented by Formula 1 above.

In the organic light emitting device of the present invention, 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, the red pixel and the green color Corresponding to the pixel, it characterized in that it further comprises a color conversion layer provided between the substrate and the organic light emitting diode or on the organic light emitting diode.

In the organic light emitting device of the present invention, the organic light emitting diode includes a third light emitting material layer positioned between the first charge generating layer and the second light emitting material layer, the second light emitting material layer and the third light emitting material layer It may further include a second charge generating layer positioned between the material layers, wherein the third light emitting material layer emits yellow-green light or red and green light.

In the organic light emitting device of the present invention, the organic light emitting diode emits yellow-green color and includes a second light emitting material layer positioned between the first light emitting material layer and the second electrode, the first light emitting material layer and the first light emitting material layer It characterized in that it further comprises a first charge generating layer positioned between the two light emitting material layers.

In the organic light emitting device of the present invention, 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 the red pixel and the green color It characterized in that it further comprises a color filter layer provided between the substrate and the organic light emitting diode or on the organic light emitting diode corresponding to the pixel and the blue pixel.

The light emitting compound of the present invention is a polycyclic aromatic compound and has a significantly improved lifetime.

Accordingly, the organic light emitting diode and the organic light emitting device including the light emitting compound of the present invention have an improved lifespan without a large increase in driving voltage and reduction in luminous efficiency.

1 is a schematic circuit diagram of an organic light emitting display device according to an embodiment of the present invention.
2 is a schematic cross-sectional view of an organic light emitting display device according to a first embodiment of the present invention.
3 is a schematic cross-sectional view of an organic light emitting diode used in an organic light emitting display device according to a first exemplary embodiment of the present invention.
4 is a schematic cross-sectional view of an organic light emitting diode having a double stack structure used in an organic light emitting diode display according to a first exemplary embodiment of the present invention.
5 is a schematic cross-sectional view of an organic light emitting display device according to a second exemplary embodiment of the present invention.
6 is a schematic cross-sectional view of an organic light emitting diode having a double stack structure used in an organic light emitting diode display according to a second exemplary embodiment of the present invention.
7 is a schematic cross-sectional view of an organic light emitting diode having a triple stack structure used in an organic light emitting diode display according to a second exemplary embodiment of the present invention.
8 is a schematic cross-sectional view of an organic light emitting display device according to a third exemplary embodiment of the present invention.

Hereinafter, a preferred embodiment according to the present invention will be described with reference to the drawings.

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

As shown in FIG. 1 , in the organic light emitting display device, a gate line GL, a data line DL, and a power line PL that cross each other and define a pixel P are formed, and the pixel P has , 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 pixel P may include a red pixel, a green pixel, and a blue pixel.

The switching thin film transistor Ts is connected to the gate line GL and the data line DL, and the driving thin film transistor Td and the storage capacitor Cst are connected between the switching thin film transistor Ts and the power line PL. do. The organic light emitting diode D is connected to the driving thin film transistor Td.

In such an organic light emitting display device, when the switching thin film transistor Ts is turned on according to a gate signal applied to the gate line GL, the data signal applied to the data line DL is applied to the switching thin film transistor It is applied to the gate electrode of the driving thin film transistor Td and one electrode of the storage capacitor Cst through Ts.

The driving thin film transistor Td is turned on according to the data signal applied to the gate electrode, and as a result, a current proportional to the data signal is transmitted from the power line 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 luminance proportional to the current flowing through the driving thin film transistor Td.

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 constantly maintained for one frame.

Accordingly, the organic light emitting display device can display a desired image.

2 is a schematic cross-sectional view of an organic light emitting diode display according to the present invention.

As shown in FIG. 2 , the organic light emitting diode display 100 includes a thin film transistor Tr positioned on a substrate 110 and an organic light emitting diode D connected to the thin film transistor Tr. For example, a red pixel, a green pixel, and a blue pixel are defined on the substrate 110 , and the organic light emitting diode D is positioned for each pixel. That is, the organic light emitting diode D emitting red, green, and blue light is provided in the red pixel, the green pixel, and the blue pixel.

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.

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.

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

When the semiconductor layer 122 is made of an oxide semiconductor material, a light blocking pattern (not shown) may be formed under the semiconductor layer 122 , and the light blocking pattern prevents light from being incident on the semiconductor layer 122 to prevent the It prevents the layer 122 from being degraded by light. Alternatively, the semiconductor layer 122 may be made of polycrystalline silicon, and in this case, both edges of the semiconductor layer 122 may be doped with impurities.

A gate insulating layer 124 made of an insulating material is formed on the semiconductor layer 122 . The gate insulating layer 124 may be made of an inorganic insulating material such as silicon oxide or silicon nitride.

A gate electrode 130 made of a conductive material such as metal is formed on the gate insulating layer 124 to correspond to the center of the semiconductor layer 122 .

In FIG. 2 , the gate insulating layer 124 is formed on the entire surface of the substrate 110 , but the gate insulating layer 124 may be patterned to have the same shape as the gate electrode 130 .

An interlayer insulating layer 132 made of an insulating material is formed on the gate electrode 130 . The interlayer insulating layer 132 may be formed of an inorganic insulating material such as silicon oxide or silicon nitride, or an organic insulating material such as benzocyclobutene or photo-acryl.

The interlayer insulating layer 132 has first and second contact holes 134 and 136 exposing both sides of the semiconductor layer 122 . The first and second contact holes 134 and 136 are positioned at both sides of the gate electrode 130 to be spaced apart from the gate electrode 130 .

Here, the first and second contact holes 134 and 136 are also formed in the gate insulating layer 124 . Alternatively, when the gate insulating layer 124 is patterned to have the same shape as the gate electrode 130 , the first and second contact holes 134 and 136 may be formed only in the interlayer insulating layer 132 .

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

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

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.

The thin film transistor Tr has a coplanar structure in which the gate electrode 130 , the source electrode 142 , and the drain electrode 144 are positioned on the semiconductor layer 122 .

Alternatively, the thin film transistor Tr may have an inverted staggered structure in which a gate electrode is positioned under a semiconductor layer and a source electrode and a drain electrode are positioned above the semiconductor layer. In this case, the semiconductor layer may be made of amorphous silicon.

Although not shown, the gate line and the data line cross each other to define a pixel, and a switching element connected to the gate line and the data line is further formed. The switching element is connected to the thin film transistor Tr as a driving element.

In addition, the power line is formed to be spaced apart from the data line or the data line in parallel, and a storage capacitor is further configured to keep the voltage of the gate electrode of the thin film transistor Tr, which is the driving element, constant during one frame. can

A protective layer 150 having a drain contact hole 152 exposing the drain electrode 142 of the thin film transistor Tr is formed to cover the thin film transistor Tr.

On the protective layer 150 , the first electrode 160 connected to the drain electrode 142 of the thin film transistor Tr through the 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 having a relatively high work function value, for example, a transparent conductive oxide (TCO). Specifically, the first electrode 160 includes indium-tin-oxide (ITO), indium-zinc-oxide (IZO), and indium-tin-zinc-oxide (indium-). It may be made of tin-zinc oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium-copper-oxide (ICO), and aluminum:zinc oxide (Al:ZnO; AZO). .

When the organic light emitting diode display 100 of the present invention is a bottom-emission type, the first electrode 160 may have a single-layer structure made of a transparent conductive oxide. On the other hand, when the organic light emitting diode display 100 of the present invention is a top-emission type, a reflective electrode or a reflective layer may be further formed under 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.

In addition, a bank layer 166 covering an edge of the first electrode 160 is formed on the passivation layer 150 . The bank layer 166 exposes the center of the first electrode 160 in correspondence with the pixel.

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. In addition, in order to increase luminous efficiency, the organic light emitting layer 162 may have a multilayer structure.

The organic light emitting layer 162 is separated from the red pixel, the green pixel, and the blue pixel. As will be described later, in the blue pixel, the organic light emitting layer 162 includes the light emitting compound represented by Chemical Formula 1, and thus, the lifespan of the organic light emitting diode D of the blue pixel is greatly improved.

A second electrode 164 is formed on the substrate 110 on which the organic light emitting layer 162 is formed. The second electrode 164 is located on the entire surface of the display area and is made of a conductive material having a relatively small work function value and may be used as a cathode. For example, the second electrode 164 may include any one of aluminum (Al), magnesium (Mg), silver (Ag), or an alloy thereof, for example, an aluminum-magnesium alloy (AlMg) or a silver-magnesium alloy (MgAg). can be made into one. When the organic light emitting diode display 100 is a top emission type, the second electrode 164 has a thin thickness and has a light transmission (semitransmission) characteristic.

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

An encapsulation film 170 is formed on the second electrode 164 to prevent external moisture from penetrating into the organic light emitting diode (D). The encapsulation film 170 may have a stacked structure of the first inorganic insulating layer 172 , the organic insulating layer 174 , and the second inorganic insulating layer 174 , but is not limited thereto. Also, the encapsulation film 170 may be omitted.

The organic light emitting display device 100 may further include a polarizing plate (not shown) for reducing reflection of external light. For example, the polarizing plate (not shown) may be a circular polarizing plate. When the organic light emitting display device 100 is a bottom light emitting type, the polarizing plate may be located under the substrate 110 . Meanwhile, when the organic light emitting diode display 100 of the present invention is a top emission type, the polarizing plate may be located on the encapsulation film 170 .

In addition, in the top emission type organic light emitting display device 100 , a cover window (not shown) may be attached on the encapsulation film 170 or the polarizing plate. In this case, since the substrate 110 and the cover window have flexible characteristics, a flexible display device may be formed.

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

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

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. In addition, one of the first electrode 160 and the second electrode 164 may be a transmissive electrode (a transflective electrode), and the other of the first electrode 160 and the second electrode 164 may be a reflective electrode.

In addition, the organic light emitting layer 162 is formed between the electron blocking layer 230 positioned between the first electrode 160 and the light emitting material layer 240 and the light emitting material layer 240 and the second electrode 164 . It may further include a hole blocking layer (hole blocking layer, 250) located in the.

Also, the organic emission layer 162 may include a hole transporting layer 220 positioned between the first electrode 160 and the electron blocking layer 230 .

In addition, the organic emission layer 162 is formed between the hole injection layer 210 positioned between the first electrode 160 and the hole transport layer 220 and the second electrode 164 and the hole blocking layer 250 . It may further include an electron injection layer (electron injection layer, 260) located in the.

The light-emitting material layer 240 includes a light-emitting compound (a first compound, 242) that is a polycyclic aromatic compound. The light emitting compound of the present invention is represented by the formula (1).

[Formula 1]

In Formula 1, n is 0 or 1, and X is one of B, P=O, and P=S. Y ₁ and Y ₂ are each independently one of NR ₁ , C(R ₂ ) ₂ , O, S, Se, Si(R ₃ ) ₂ , and Y ₃ is O or S. Each of R ₁ to R ₃ is independently hydrogen, deuterium, a C1 to C10 alkyl group unsubstituted or substituted with deuterium, a C6 to C30 arylamine group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, unsubstituted or It is selected from a C6 to C30 aryl group substituted with deuterium or a C1 to C10 alkyl group, and a C5 to C30 heteroaryl group which is unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group. In addition, each of R ₄ to R ₇ is independently hydrogen, deuterium, a C1 to C10 alkyl group unsubstituted or substituted with deuterium, a C6 to C30 arylamine group which is unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, substituted Unsubstituted or selected from a C6 to C30 aryl group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, a C5 to C30 heteroaryl group unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group, or adjacent two are connected to each other to form a ring (ring ) is achieved. In addition, each of R ₈ and R ₉ is independently hydrogen, deuterium, a C1 to C10 alkyl group unsubstituted or substituted with deuterium, a C6 to C30 arylamine group which is unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, substituted Unsubstituted or selected from a C6 to C30 aryl group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, or a C5 to C30 heteroaryl group unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group, or connected to each other to form a ring.

Each of Ring A and Ring E is independently selected from a substituted or unsubstituted 6 membered cycloalkyl ring, a substituted or unsubstituted 6 membered aromatic ring, a substituted or unsubstituted heteroaromatic ring (or condensed heteroaromatic ring) .

In this case, the ring formed by connecting two adjacent ones of R ₄ to R ₇ and the ring formed by connecting R ₈ and R ₉ are each independently a C6 to C30 aromatic ring or a C5 to C30 heteroaromatic ring (or heteroaromatic condensation) ring) may be For example, the C6 to C30 aromatic ring may be a benzene ring or a naphthalene ring, and the C5 to C30 heteroaromatic ring may be a thiophene ring, a furan ring, a benzothiophene ring, or a benzofuran ring.

In addition, in each of ring A and ring E, hydrogen may be substituted with at least one of deuterium, a C1 to C10 alkyl group, a C6 to C30 aryl group, and a C5 to C30 heteroaryl group.

For example, in Formula 1, n may be 0. That is, the pentagonal ring including Y ₃ may be directly connected to X and Y ₂ , and the light-emitting compound of Formula 1 may be represented by Formula 2-1.

[Formula 2-1]

In addition, in Formula 2-1, X may be B, each of Y ₁ and Y ₂ may be NR ₁ , and each of the A ring and the E ring may be a substituted or unsubstituted benzene ring. That is, the light emitting compound of Formula 1 may be represented by Formula 2-2.

[Formula 2-2]

In Formula 2-2, each of R ₂₁ to R ₂₇ is independently hydrogen, deuterium, a C1 to C10 alkyl group unsubstituted or substituted with deuterium, an unsubstituted or deuterium or a C1 to C10 alkyl group substituted with a C1 to C10 alkyl group; It is selected from an amine group, a C6 to C30 aryl group unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group, a C5 to C30 heteroaryl group which is unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group.

For example, in Formula 2-2, R ₁ may be a C6 to C30 aryl group (eg, phenyl), and adjacent two of R ₄ to R ₇ are connected to each other to form a C6 to C30 aromatic ring (eg, benzene ring) and the other two may be hydrogen. In addition, R ₂₁ to R ₂₇ may be hydrogen.

Meanwhile, in Formula 1, n may be 1. That is, the light emitting compound of Formula 1 may be represented by Formula 3-1.

[Formula 3-1]

In addition, in Formula 3-1, X may be B, each of Y ₁ and Y ₂ may be NR ₁ , and each of the A ring and the E ring may be a substituted or unsubstituted benzene ring. That is, the light emitting compound of Formula 1 may be represented by Formula 3-2.

[Formula 3-2]

In Formula 3-2, each of R ₃₁ to R ₃₇ is independently hydrogen, deuterium, a C1 to C10 alkyl group unsubstituted or substituted with deuterium, an unsubstituted or deuterium or a C1 to C10 alkyl group substituted with a C1 to C10 alkyl group; It is selected from an amine group, a C6 to C30 aryl group unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group, a C5 to C30 heteroaryl group which is unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group.

For example, in Formula 3-2, R ₁ may be a C6 to C30 aryl group (eg, phenyl), and adjacent two of R ₄ to R ₇ or R ₈ and R ₉ are connected to each other to form C6 to C30 of an aromatic ring (eg, a benzene ring), and the other two of R ₄ to R ₇ may be hydrogen. In addition, R ₃₁ to R ₃₇ may be hydrogen.

Meanwhile, in Formula 3-1, ring E may be a condensed ring having a heteroaromatic ring. That is, the light emitting compound of Formula 1 may be represented by Formula 3-3.

[Formula 3-3]

In Formula 3-3, Y ₄ is one of NR ₁ , C(R ₂ ) ₂ , O, S, Se, and Si(R ₃ ) ₂ . each of R ₁₀ to R ₁₃ is independently hydrogen, deuterium, a C1 to C10 alkyl group unsubstituted or substituted with deuterium, a C6 to C30 arylamine group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, unsubstituted or A C6 to C30 aryl group substituted with deuterium or a C1 to C10 alkyl group, a C5 to C30 heteroaryl group unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group, or adjacent two are connected to each other to form a ring. In addition, each of R ₁₄ and R ₁₅ is independently hydrogen, deuterium, a C1 to C10 alkyl group unsubstituted or substituted with deuterium, a C6 to C30 arylamine group which is unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, substituted Unsubstituted or selected from a C6 to C30 aryl group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, or a C5 to C30 heteroaryl group unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group, or connected to each other to form a ring.

In this case, the ring formed by connecting two adjacent ones of R ₁₀ to R ₁₃ and the ring formed by connecting R ₁₄ and R ₁₅ are each independently a C6 to C30 aromatic ring or a C5 to C30 heteroaromatic ring (or heteroaromatic condensation) ring) may be

Also, in Formula 3-3, X may be B, Y ₁ , Y ₂ may each be NR ₁ , and ring A may be a benzene ring. That is, the light emitting compound of Formula 1 may be represented by Formula 3-4.

[Formula 3-4]

In Formula 3-4, each of R ₄₁ to R ₄₃ is independently hydrogen, deuterium, a C1 to C10 alkyl group unsubstituted or substituted with deuterium, or a C6 to C30 aryl group which is unsubstituted or substituted with deuterium or a C1 to C10 alkyl group. It is selected from an amine group, a C6 to C30 aryl group unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group, a C5 to C30 heteroaryl group which is unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group.

For example, in Formula 3-4, R ₁ may be a C6 to C30 aryl group (eg, phenyl), and adjacent two of R ₄ to R ₇ or R ₈ and R ₉ are connected to each other to form C6 to C30 may form an aromatic ring of (eg, a benzene ring) or adjacent two of R ₁₀ to R ₁₃ or R ₁₄ and R ₁₅ may be connected to each other to form a C6 to C30 aromatic ring (eg, a benzene ring). A remainder of R ₄ to R ₇ and a remainder of R ₁₀ to R ₁₃ and R ₄₁ to R ₄₃ may be hydrogen.

The light emitting compound of the present invention represented by Formula 1 may be one of the compounds represented by Formula 4.

[Formula 4]

The light emitting compound of the present invention represented by Formula 1 emits blue light and is used in the light emitting material layer 240 of the organic light emitting diode (D), and thus the lifespan of the organic light emitting diode (D) and the organic light emitting device 100 is greatly increased. do.

[Synthesis Example]

1. Synthesis of compound 1-1

(1) compound I1-1c

[Scheme 1-1]

In a 500 mL reactor, compound I1-1a 8.5 g (50 mmol), compound I1-1b 20.2 g (50 mmol), palladium acetate 0.45 g (2 mmol), sodium tert-butoxide 18.9 g (196 mmol), tritertiary 0.8 g (4 mmol) of butylphosphine and 300 mL of toluene were added, and the mixture was stirred under reflux for 5 hours. After completion of the reaction, the filtrate was concentrated by filtration and separated by column chromatography to obtain 16.1 g of compound I1-1c. (yield 60%)

(2) compound 1-1

[Scheme 1-2]

6.7 g (12.5 mmol) of compound I1-1c and 60 mL of tert-butylbenzene were placed in a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. After that, heptane was removed by blowing nitrogen at 60 °C. 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 dropwise addition, the mixture was stirred at 120 °C for 2 hours. After completion of the reaction, an aqueous sodium acetate solution was added at room temperature and stirred. After extraction with ethyl acetate, the organic layer was concentrated and separated by column chromatography to obtain 1.2 g of Compound 1-1. (yield 19%)

2. Synthesis of compound 1-2

(1) compound I1-2c

[Scheme 2-1]

In a 500 mL reactor, compound I1-2a 8.5 g (50 mmol), compound I1-2b 20.2 g (50 mmol), palladium acetate 0.45 g (2 mmol), sodium tert-butoxide 18.9 g (196 mmol), tritertiary 0.8 g (4 mmol) of butylphosphine and 300 mL of toluene were added, and the mixture was stirred under reflux for 5 hours. After the reaction was completed, the filtrate was concentrated by filtration and separated by column chromatography to obtain 16.1 g of compound I1-2c. (yield 60%)

(2) compound 1-2

[Scheme 2-2]

In a 500 mL reactor, 6.7 g (12.5 mmol) of compound I1-2c and 60 mL of tert-butylbenzene were placed. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. After that, heptane was removed by blowing nitrogen at 60 °C. 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 dropwise addition, the mixture was stirred at 120 °C for 2 hours. After completion of the reaction, an aqueous sodium acetate solution was added at room temperature and stirred. After extraction with ethyl acetate, the organic layer was concentrated and separated by column chromatography to obtain 1.1 g of Compound 1-2. (yield 18%)

3. Synthesis of compound 1-3

(1) compound I1-3c

[Scheme 3-1]

In a 500 mL reactor, compound I1-3a 8.5 g (50 mmol), compound I1-3b 20.2 g (50 mmol), palladium acetate 0.45 g (2 mmol), sodium tert-butoxide 18.9 g (196 mmol), tritertiary 0.8 g (4 mmol) of butylphosphine and 300 mL of toluene were added, and the mixture was stirred under reflux for 5 hours. After completion of the reaction, the filtrate was concentrated by filtration and separated by column chromatography to obtain 17.2 g of compound I1-3c. (Yield 64%)

(2) compound 1-3

[Scheme 3-2]

6.7 g (12.5 mmol) of compound I1-3c and 60 mL of tert-butylbenzene were placed in a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. After that, heptane was removed by blowing nitrogen at 60 °C. 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 dropwise addition, the mixture was stirred at 120 °C for 2 hours. After completion of the reaction, an aqueous sodium acetate solution was added at room temperature and stirred. After extraction with ethyl acetate, the organic layer was concentrated and separated by column chromatography to obtain 1.2 g of Compound 1-3. (yield 19%)

4. Synthesis of compound 1-4

(1) compound I1-4c

[Scheme 4-1]

In a 500 mL reactor, compound I1-4a 8.5 g (50 mmol), compound I1-4b 21.0 g (50 mmol), palladium acetate 0.45 g (2 mmol), sodium tert-butoxide 18.9 g (196 mmol), tritertiary 0.8 g (4 mmol) of butylphosphine and 300 mL of toluene were added, and the mixture was stirred under reflux for 5 hours. After completion of the reaction, the filtrate was concentrated by filtration and separated by column chromatography to obtain 17.1 g of compound I1-4c. (Yield 62%)

(2) compound 1-4

[Scheme 4-2]

6.9 g (12.5 mmol) of compound I1-4c and 60 mL of tert-butylbenzene were placed in a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. After that, heptane was removed by blowing nitrogen at 60 °C. 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 dropwise addition, the mixture was stirred at 120 °C for 2 hours. After completion of the reaction, an aqueous sodium acetate solution was added at room temperature and stirred. After extraction with ethyl acetate, the organic layer was concentrated and separated by column chromatography to obtain 1.3 g of Compound 1-4. (yield 19%)

5. Synthesis of compound 1-6

(1) compound I1-6c

[Scheme 5-1]

In a 500 mL reactor, compound I1-6a 8.5 g (50 mmol), compound I1-6b 21.0 g (50 mmol), palladium acetate 0.45 g (2 mmol), sodium tert-butoxide 18.9 g (196 mmol), tritertiary 0.8 g (4 mmol) of butylphosphine and 300 mL of toluene were added, and the mixture was stirred under reflux for 5 hours. After completion of the reaction, the filtrate was concentrated by filtration and separated by column chromatography to obtain 16.6 g of compound I1-6c. (yield 60%)

(2) compound 1-6

[Scheme 5-2]

6.9 g (12.5 mmol) of compound I1-6c and 60 mL of tert-butylbenzene were placed in a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. After that, heptane was removed by blowing nitrogen at 60 °C. 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 dropwise addition, the mixture was stirred at 120 °C for 2 hours. After completion of the reaction, an aqueous sodium acetate solution was added at room temperature and stirred. After extraction with ethyl acetate, the organic layer was concentrated and separated by column chromatography to obtain 1.4 g of Compound 1-6. (Yield 21%)

6. Synthesis of compound 2-1

(1) compound I2-1c

[Scheme 6-1]

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

(2) compound 2-1

[Scheme 6-2]

7.3 g (12.5 mmol) of compound I2-1c and 60 mL of tert-butylbenzene were placed in a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. After that, heptane was removed by blowing nitrogen at 60 °C. 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 dropwise addition, the mixture was stirred at 120 °C for 2 hours. After completion of the reaction, an aqueous sodium acetate solution was added at room temperature and stirred. After extraction with ethyl acetate, the organic layer was concentrated and separated by column chromatography to obtain 1.4 g of Compound 2-1. (yield 20%)

7. Synthesis of compound 2-2

(1) compound I2-2c

[Scheme 7-1]

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

(2) compound 2-2

[Scheme 7-2]

7.3 g (12.5 mmol) of compound I2-2c and 60 mL of tert-butylbenzene were placed in a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. After that, heptane was removed by blowing nitrogen at 60 °C. 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 dropwise addition, the mixture was stirred at 120 °C for 2 hours. After completion of the reaction, an aqueous sodium acetate solution was added at room temperature and stirred. After extraction with ethyl acetate, the organic layer was concentrated and separated by column chromatography to obtain 1.5 g of Compound 2-2. (Yield 22%)

8. Synthesis of compound 2-3

(1) compound I2-3c

[Scheme 8-1]

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

(2) compound 2-3

[Scheme 8-2]

7.3 g (12.5 mmol) of compound I2-3c and 60 mL of tert-butylbenzene were placed in a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. After that, heptane was removed by blowing nitrogen at 60 °C. 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 dropwise addition, the mixture was stirred at 120 °C for 2 hours. After completion of the reaction, an aqueous sodium acetate solution was added at room temperature and stirred. After extraction with ethyl acetate, the organic layer was concentrated and separated by column chromatography to obtain 1.6 g of compound 2-3. (yield 20%)

9. Synthesis of compound 2-4

(1) compound I2-4c

[Scheme 9-1]

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

(2) compound 2-4

[Scheme 9-2]

7.3 g (12.5 mmol) of compound I2-4c and 60 mL of tert-butylbenzene were placed in a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. After that, heptane was removed by blowing nitrogen at 60 °C. 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 dropwise addition, the mixture was stirred at 120 °C for 2 hours. After completion of the reaction, an aqueous sodium acetate solution was added at room temperature and stirred. After extraction with ethyl acetate, the organic layer was concentrated and separated by column chromatography to obtain 1.5 g of Compound 2-4. (Yield 21%)

10. Synthesis of compound 2-5

(1) compound I2-5c

[Scheme 10-1]

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

(2) compound 2-5

[Scheme 10-2]

9.1 g (12.5 mmol) of compound I2-5c and 60 mL of tert-butylbenzene were placed in a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. After that, heptane was removed by blowing nitrogen at 60 °C. 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 dropwise addition, the mixture was stirred at 120 °C for 2 hours. After completion of the reaction, an aqueous sodium acetate solution was added at room temperature and stirred. After extraction with ethyl acetate, the organic layer was concentrated and separated by column chromatography to obtain 1.6 g of Compound 2-5. (yield 18%)

11. Synthesis of compound 2-8

(1) compound I2-8c

[Scheme 11-1]

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

(2) compound 2-8

[Scheme 11-2]

9.1 g (12.5 mmol) of compound I2-8c and 60 mL of tert-butylbenzene were placed in a 500 mL reactor. 45 mL (37.5 mmol) of n-butyllithium was added dropwise at -78°C. After dropwise addition, the mixture was stirred at 60° C. for 3 hours. After that, heptane was removed by blowing nitrogen at 60 °C. 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 dropwise addition, the mixture was stirred at 120 °C for 2 hours. After completion of the reaction, an aqueous sodium acetate solution was added at room temperature and stirred. After extraction with ethyl acetate, the organic layer was concentrated and separated by column chromatography to obtain 1.5 g of Compound 2-8. (Yield 17%)

In the light emitting material layer 240 , the first compound 242 may be used as a dopant (light emitting body) and may emit blue light.

In addition, the light emitting material layer 240 may further include a second compound 244 used as a host. In this case, in the light emitting material layer 240 , the first compound 242 may have an amount of about 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 angstroms, preferably 50 to 400 angstroms, and more preferably 100 to 300 angstroms.

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

[Formula 5]

In Formula 5, Ar ₁ and Ar ₂ each is independently a substituted or unsubstituted C ₆ -C ₃₀ aryl group or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, and L is a single bond or a substituted or unsubstituted a cyclic C ₆ -C ₂₀ arylene group. In this case, hydrogen may be unsubstituted or some or all of it may be substituted with deuterium.

In formula (5), each of Ar1 and Ar2 may be selected from phenyl, naphthyl, dibenzofuranyl, and condensed dibenzofuranyl, and L may be a single bond or phenylene.

For example, Ar1 may be selected from naphthyl, dibenzofuranyl, phenyldibenzofuranyl, and condensed dibenzofuranyl, and Ar2 may be selected from phenyl and naphthyl. In addition, both Ar1 and Ar2 may be naphthyl and L may be a single bond or phenylene.

In addition, some or all of the hydrogens of the anthracene core may be substituted with deuterium, or some or all of the hydrogens of Ar1, Ar2, and L may be substituted with deuterium. Alternatively, some or all of hydrogens in each of the anthracene core, Ar1, Ar2, and L may be substituted with deuterium.

The second compound 244 represented by Formula 5 may be one of the compounds represented by Formula 6 below.

[Formula 6]

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), 1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile (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), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H It may include at least one compound of -fluoren-2-amine Alternatively, the hole injection layer 210 may include a compound of Formula 13 below (host) and a compound of Formula 14 below (dopant).

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-butylphenyl)-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), N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine; It may include at least one compound of N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl-4-amine. The transport layer 220 may be formed of a compound of Formula 13 below.

The electron blocking layer 230 is located between the hole transport layer 220 and the light emitting material layer 240 to prevent electron movement from the light emitting material layer 240 to the hole transport layer 220. The electron blocking material 232 is an amine derivative. ) is included. For example, the electron blocking material 232 of the electron blocking layer 230 may be represented by the following Chemical Formula 7 .

[Formula 7]

In Formula 7, L is a C6-C30 arylene group, and a is 0 or 1. In addition, R ₁ , R ₂ Each is independently a substituted or unsubstituted C6~ C30 aryl group or a substituted or unsubstituted C5~ C30 heteroaryl group.

For example, L may be phenylene, R ₁ , R ₂ each is independently biphenyl, fluorenyl (9,9-dimethyl-9H-fluorenyl), phenylcarbazoyl, carbazoylphenyl, dibenzothiophenyl or dibenzofuranyl.

That is, the electron blocking material 232 may be an amine derivative substituted with a spirofluorene group.

The electron blocking material 232 of Formula 7 may be one of the compounds of Formula 8 below.

[Formula 8]

In addition, the hole blocking layer 250 is located between the light emitting material layer 240 and the electron injection layer 260 to prevent the movement of holes from the light emitting material layer 240 to the electron injection layer 260 is a hole blocking layer ( 250 includes a hole blocking material 252 . For example, the hole blocking material 252 may be an azine derivative represented by Formula 9.

[Formula 9]

In Formula 9, each of Y ₁ to Y ₅ is independently CR ₁ or N, and one to three of them are N. In this case, R ₁ is independently a C6-C30 aryl group. In addition, L is a C6~ C30 allylene group, R ₂ is a C6~ C30 aryl group or a C5~ C30 heteroaryl group, R ₃ is hydrogen or two adjacent ones form a condensed ring. In addition, a is 0 or 1, b is 1 or 2, and c is an integer of 0-4.

For example, a C6~ C30 aryl group that may be R2 is substituted with another C6~ C30 aryl group or a C5~ C30 heteroaryl group, or spies together with a C10~ C30 condensed aryl ring or a C10~ C30 condensed heteroaryl ring can be structured with Here, another C6~ C30 aryl group may be substituted with a C6~ C30 aryl group or a C5~ C30 heteroaryl group, or form a spiro structure with a C10~ C30 condensed aryl ring.

The hole blocking material 252 of Formula 9 may be one of the compounds of Formula 10 below.

[Formula 10]

Alternatively, the hole blocking material 252 of the hole blocking layer 250 may be a benzimidazole derivative represented by Formula 11-1 or Formula 11-2.

[Formula 11-1]

In Formula 11-1, Ar is a C10~ C30 arylene group, R ₁ is a C6~ C30 aryl group or a C5~ C30 heteroaryl group, R ₂ is hydrogen, a C1~ C10 alkyl group, or a C6~ C30 It is an aryl group.

[Formula 11-2]

In Formula 11-2, Ar is a C10~ C30 arylene group, R ₁ is a C6~ C30 aryl group or a C5~ C30 heteroaryl group, R ₂ , R ₃ Each is independently hydrogen, C1~ C10 It is an alkyl group or a C6-C30 aryl group. Each of the C6~ C30 aryl group or the C5~ C30 heteroaryl group may be substituted with a C1~ C10 alkyl group.

For example, Ar may be naphthylene or anthracenylene, R ₁ may be benzimidazoyl or phenyl, and R ₂ may be methyl, ethyl or phenyl.

The hole blocking material 252 of Formula 11-1 or Formula 11-2 may be one of the compounds of Formula 12.

[Formula 12]

The hole blocking material 252 of the hole blocking layer 250 may include one of a compound of Formula 9 and a compound of Formula 11-1 or Formula 11-2.

In this case, the thickness of the light emitting material layer 240 may be greater than the thickness of each of the electron blocking layer 230 and the hole blocking layer 250 and smaller than the thickness of the hole transport layer 220 . For example, the light emitting material layer 240 has a thickness of about 150 to 250 Å, each of the electron blocking layer 230 and the hole blocking layer 250 has a thickness of about 50 to 150 Å, and the hole transport layer 220 is It 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.

Meanwhile, the hole blocking layer 250 may include both the compound of Formula 9 and the compound of Formula 11-1 or Formula 11-2 as the hole blocking material 252 . For example, in the hole blocking layer 250 , the hole blocking material of Formula 9 and the hole blocking material of Formula 11-1 or Formula 11-2 may have the same weight ratio.

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 . Also, 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. In addition, each of the hole blocking layers 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.

The compound (hole blocking material) of Formula 9 and/or Formula 11-1 (or Formula 11-2) has electron transport properties, so the electron transport layer may be omitted, and thus the hole blocking layer 250 is an electron injection layer ( 260 ) or in direct contact with the second electrode 164 .

The electron injection layer 260 may include at least one of an alkali metal such as Li, an alkali halide-based material such as LiF, CsF, NaF, BaF ₂ , and/or an organometallic material such as Liq, lithium benzoate, and sodium stearate. , but is not limited thereto. Alternatively, the electron injection layer 260 may include the compound of Formula 15 (host) and an alkali metal (dopant).

In the organic light emitting diode (D) of the present invention, the light emitting material layer 240 includes the light emitting compound 242 of Formula 1, and thus the lifespan of the organic light emitting diode (D) and the organic light emitting display device 100 is prolonged. greatly improved

[Organic light emitting diode]

Anode (ITO, 0.5mm), hole injection layer (Formula 13 (97wt%) + Formula 14 (3wt%), 100Å), hole transport layer (Formula 13, 1000Å), electron blocking layer (Compound EBL-11 of Formula 8, 100Å), light emitting material layer (host (compound H-1 of Formula 6, 98wt%) + dopant (2wt%), 200Å), hole blocking layer (compound E1 of Formula 10, 100Å), electron injection layer (Formula 15 ( 98wt%)+Li (2wt%), 200Å), and a cathode (Al, 500Å) were sequentially stacked, and an encapsulation film was formed using UV curing epoxy and a moisture getter to fabricate an organic light emitting diode.

[Formula 13]

[Formula 14]

[Formula 15]

(1) Comparative Example 1 and Comparative Example 2 (Ref1 ~ Ref2)

Each of the compounds of Formula 16 (Ref-1) and Formula 17 (Ref-2) was used as a dopant to form a light emitting material layer.

(2) Experimental Examples 1 to 11 (Ex1 to Ex11)

Compound 1-1 of Formula 4, Compound 1-2, Compound 1-3, Compound 1-4, Compound 1-6, Compound 2-1, Compound 2-2, Compound 2-3, Compound 2-4, Compound 2 A light emitting material layer was formed by using -5 and compound 2-8 as dopants, respectively.

[Formula 16]

[Formula 17]

The characteristics (driving voltage (V), external quantum efficiency (EQE), color coordinates, and lifetime (T95)) of the organic light emitting diodes manufactured in Comparative Examples 1 and 2 and Experimental Examples 1 to 11 were measured and shown in Table 1 described. The properties of organic light-emitting diodes were measured at room temperature using a current source (KEITHLEY) and a photometer PR 650. The driving voltage, external quantum efficiency, and color coordinates were measured under the current density condition of 10 mA/cm ² , and the lifetime was measured at 40° C., 22.5 mA/cm ² The time at which the lifetime reached 95% was measured.

[Table 1]

As shown in Table 1, compared with 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 using the light emitting compound of the present invention as a dopant is greatly improved.

4 is a schematic cross-sectional view of an organic light emitting diode having a double stack structure used in an organic light emitting diode display according to a first exemplary embodiment of the present invention.

As shown in FIG. 4 , the organic light emitting diode D is positioned between the first and second electrodes 160 and 164 facing each other and the first and second electrodes 160 and 164 and includes an organic light emitting layer ( 162), wherein the organic light emitting layer 162 includes a first light emitting unit 310 including a first light emitting material layer 320 and a second light emitting unit 330 including a second light emitting material layer 340 and a charge generation layer 350 positioned between the first light emitting unit 310 and the second light emitting unit 330 . The organic light emitting display device 100 of FIG. 2 may include a red pixel, a green pixel, and a blue pixel, and the organic light emitting diode D may be located in the blue pixel.

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. In addition, one of the first electrode 160 and the second electrode 164 may be a transmissive electrode (a transflective electrode), and the other of the first electrode 160 and the second electrode 164 may be a reflective electrode.

The charge generating layer 350 is positioned between the first and second light emitting units 310 and 330 , and the first light emitting unit 310 , the charge generating layer 350 , and the second light emitting unit 330 are formed as a first electrode. It is sequentially stacked on (160). That is, the first light emitting part 310 is positioned 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 . is located in

The first light emitting unit 310 includes a first light emitting material layer 320 . In addition, the first light emitting unit 310 includes a first electron blocking layer 316 , a first light emitting material layer 320 , and a charge generating layer positioned between the first electrode 160 and the first light emitting material layer 320 . A first hole blocking layer 318 positioned between the 350 may be further included.

In addition, the first light emitting part 310 includes a first hole transport layer 314 positioned between the first electrode 160 and the first electron blocking layer 316 , the first electrode 160 , and the first hole transport layer 314 . ) may further include a hole injection layer 312 positioned between them.

The first light emitting material layer 320 includes the light emitting compound represented by 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 Formula 4 .

The first light emitting material layer 320 may further include a second compound 324 . For example, the second compound 324 may be one of the compounds represented by Formula 5 and represented by Formula 6.

In this case, 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 is 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 wt%. In order to realize sufficient efficiency and lifespan, the first compound 322 may have about 0.1 to 10 wt%, preferably about 1 to 5 wt%.

The first electron blocking layer 316 may include the compound represented by Chemical Formula 7 as an electron blocking material. In addition, the first hole blocking layer 318 may include at least one of a compound of Formula 9 and a compound of Formula 11-1 or Formula 11-2 as a hole blocking material.

The second light emitting unit 330 includes a second light emitting material layer 340 . In addition, the second light emitting unit 330 includes a second electron blocking layer 334 , a second light emitting material layer 340 , and a second electrode positioned between the charge generating layer 350 and the second light emitting material layer 340 . A second hole blocking layer 336 positioned between the 164 may be further included.

In addition, the second light emitting unit 330 includes a second hole transport layer 332 , a second hole blocking layer 336 and a second electrode positioned between the charge generation layer 350 and the second electron blocking layer 334 ( An electron injection layer 338 positioned between 164 may be further included.

The second light emitting material layer 340 includes the light emitting compound represented by 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 Formula 4 .

The second light emitting material layer 340 may further include a fourth compound 344 . For example, the fourth compound 344 may be one of the compounds represented by Formula 5 and represented by Formula 6.

In this case, 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 is 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 wt%. In order to realize sufficient efficiency and lifespan, the third compound 342 may have an amount of about 0.1 to 10% by weight, preferably about 1 to 5% by weight.

The third compound 342 of the second light-emitting material 340 may be the same as or different from the first compound 322 of the first light-emitting material layer 320 , and the fourth compound 344 of the second light-emitting material 340 may be different. ) may be the same as or different from the second compound 324 of the first light emitting material layer 320 . Also, the weight ratio of the first compound 322 in the first light emitting material layer 320 to the weight ratio of the third compound 342 in the second light emitting material layer 340 may be the same or different.

The second electron blocking layer 334 may include the compound represented by Chemical Formula 7 as an electron blocking material. In addition, the second hole blocking layer 336 may include at least one of a compound of Formula 9 and a compound of Formula 11-1 or Formula 11-2 as a hole blocking material.

The charge generation layer 350 is positioned between the first light emitting part 310 and the second light emitting part 330 . That is, the first light emitting unit 310 and the second light emitting unit 330 are connected by the charge generation layer 350 . The charge generation layer 350 may be a PN junction charge generation layer in which the N-type charge generation layer 352 and the P-type charge generation layer 354 are joined.

The N-type charge generation layer 352 is positioned between the first electron blocking layer 318 and the second hole transport layer 332 , and the P-type charge generation layer 354 includes the N-type charge generation layer 352 and the second hole It is located between the transport layers 332 .

In such an organic light emitting diode (D), each of the first and second light emitting material layers 320 and 340 includes the light emitting compound 242 of Formula 1, and thus the organic light emitting diode (D) and the organic light emitting display device. The lifetime of (100) is greatly improved.

Furthermore, since the blue light emitting units are stacked in a double stack structure, an image having a high color temperature may be realized in the organic light emitting diode display 100 .

5 is a schematic cross-sectional view of an organic light emitting diode display according to a second embodiment of the present invention. It is a cross section. 7 is a schematic cross-sectional view of an organic light emitting diode having a triple stack structure used in an organic light emitting diode display according to a second exemplary embodiment of the present invention.

As shown in FIG. 5 , the organic light emitting diode display 400 includes a first substrate 410 on which a red pixel RP, a green pixel GP, and a blue pixel BP are defined, and a first substrate 410 . a second substrate 470 facing the A color filter layer 480 positioned between the substrates 470 is included.

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.

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

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

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

A gate electrode 430 made of a conductive material such as metal is formed on the gate insulating layer 424 to correspond to the center of the semiconductor layer 422 .

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

The interlayer insulating layer 432 has first and second contact holes 434 and 436 exposing both sides of the semiconductor layer 422 . The first and second contact holes 434 and 436 are positioned at both sides of the gate electrode 430 to be spaced apart from the gate electrode 430 .

A source electrode 440 and a drain electrode 442 made of a conductive material such as metal are formed on the interlayer insulating layer 432 .

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

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.

Although not shown, the gate line and the data line cross each other to define a pixel, and a switching element connected to the gate line and the data line is further formed. The switching element is connected to the thin film transistor Tr as a driving element.

In addition, the power line is formed to be spaced apart from the data line or the data line in parallel, and a storage capacitor is further configured to keep the voltage of the gate electrode of the thin film transistor Tr, which is the driving element, constant during one frame. can

A protective layer 450 having a drain contact hole 452 exposing the drain electrode 442 of the thin film transistor Tr is formed to cover the thin film transistor Tr.

On the passivation layer 450 , the 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 having a relatively high work function value, for example, a transparent conductive oxide (TCO). Specifically, the first electrode 460 is formed of indium-tin-oxide (ITO), indium-zinc-oxide (IZO), and indium-tin-zinc-oxide (indium-). It may be made of tin-zinc oxide (ITZO), tin oxide (SnO), zinc oxide (ZnO), indium-copper-oxide (ICO), and aluminum:zinc oxide (Al:ZnO; AZO). .

When the organic light emitting diode display 400 of the present invention is a bottom-emission type, the first electrode 460 may have a single-layer structure made of a transparent conductive oxide. On the other hand, when the organic light emitting diode display 400 of the present invention is a top-emission type, a reflective electrode or a reflective layer may be further formed under 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.

A bank layer 466 covering an edge of the first electrode 460 is formed on the passivation layer 450 . The bank layer 466 exposes the center of the first electrode 460 corresponding to the red, green, and blue pixels Rp, GP, and BP. Since the organic light emitting diode D emits white light from the red, green, and blue pixels Rp, GP, and BP, the emission layer 462 does not need to be separated from the red, green, and blue pixels Rp, GP, and BP. It may be formed as a common layer. The bank layer 466 is formed to prevent current leakage from the edge of the first electrode 460 , and the bank layer 466 may be omitted.

An organic emission layer 462 is formed on the first electrode 460 .

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 and a second light emitting part 730 including a second light emitting material layer 740 . and a charge generation layer 750 positioned between the first light emitting unit 710 and the second light emitting unit 730 .

The charge generating layer 750 is positioned between the first and second light emitting units 710 and 730 , and the first light emitting unit 710 , the charge generating layer 750 , and the second light emitting unit 730 are formed as a first electrode. are sequentially stacked on 460 . That is, the first light emitting part 710 is positioned between the first electrode 460 and the charge generating layer 750 , and the second light emitting part 730 is positioned between the second electrode 464 and the charge generating layer 750 . is located in

The first light emitting unit 710 includes a first light emitting material layer 720 . In addition, the first light emitting unit 710 includes a first electron blocking layer 716 , a first light emitting material layer 720 , and a charge generating layer positioned between the first electrode 460 and the first light emitting material layer 720 . A first hole blocking layer 718 positioned between the 750 may be further included.

In addition, the first light emitting unit 710 includes a first hole transport layer 714 positioned between the first electrode 460 and the first electron blocking layer 716 , the first electrode 460 , and the first hole transport layer 714 . ) may further include a hole injection layer 712 positioned between them.

In this case, the first light-emitting material layer 720 includes the light-emitting compound represented by 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 Formula 4 .

The first light emitting material layer 720 may further include a second compound 724 . For example, the second compound 724 may be one of the compounds represented by Formula 5 and represented by Formula 6.

In this case, 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 is 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 wt%. In order to realize sufficient efficiency and lifespan, the first compound 722 may have about 0.1 to 10 wt%, preferably about 1 to 5 wt%.

The first electron blocking layer 716 may include the compound represented by Chemical Formula 7 as an electron blocking material. In addition, the first hole blocking layer 718 may include at least one of a compound of Formula 9 and a compound of Formula 11-1 or Formula 11-2 as a hole blocking material.

The second light emitting unit 730 includes a second light emitting material layer 740 . In addition, the second light emitting unit 730 includes a second electron blocking layer 734 , a second light emitting material layer 740 , and a second electrode positioned between the charge generating layer 750 and the second light emitting material layer 740 . A second hole blocking layer 736 positioned between the 464 may be further included.

In addition, the second light emitting unit 730 includes a second hole transport layer 732, a second hole blocking layer 736, and a second electrode positioned between the charge generation layer 750 and the second electron blocking layer 734. An electron injection layer 738 interposed between 464 may be further included.

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.

In the second light emitting material layer 740 , the host 745 has about 70 to 99.9 wt%, and the yellow-green dopant 743 has about 0.1 to 30 wt%. In order to realize sufficient efficiency and lifetime, the yellow-green dopant 743 may have about 0.1 to 10 wt%, preferably about 1 to 5 wt%.

The second electron blocking layer 734 may include the compound represented by Chemical Formula 7 as an electron blocking material. In addition, the second hole blocking layer 736 may include at least one of a compound of Formula 9 and a compound of Formula 11-1 or Formula 11-2 as a hole blocking material.

The charge generation layer 750 is positioned between the first light emitting part 710 and the second light emitting part 730 . That is, the first light emitting unit 710 and the second light emitting unit 730 are connected by the charge generation layer 750 . The charge generation layer 750 may be a PN junction charge generation layer in which the N-type charge generation layer 752 and the P-type charge generation layer 754 are joined.

The N-type charge generation layer 752 is positioned between the first electron blocking layer 718 and the second hole transport layer 732 , and the P-type charge generation layer 754 includes the N-type charge generation layer 752 and the second hole It is located between the transport layers 732 .

In FIG. 6 , the first light emitting material layer 720 positioned between the first electrode 460 and the charge generating layer 750 includes a first compound 722 which is a light emitting compound of the present invention and a second compound 722 which is an anthracene derivative ( 724 , and the second light-emitting material layer 740 positioned between the second electrode 764 and the charge generating layer 750 is a yellow-green light-emitting material layer. On the contrary, the first light emitting material layer 720 positioned between the first electrode 460 and the charge generating layer 750 is a yellow-green light emitting material layer, and between the second electrode 764 and the charge generating layer 750 . The positioned second light emitting material layer 740 may be a blue light emitting material layer including the light emitting compound of the present invention and an anthracene derivative.

In such an organic light emitting diode (D), the first light emitting material layer 720 includes the light emitting compound 242 of Formula 1, and thus the lifespan of the organic light emitting diode (D) and the organic light emitting display device 100 is prolonged. greatly improved

In addition, the organic light emitting diode D provided with the first light emitting unit 710 emitting blue light and the second light emitting unit 730 emitting yellow green color may emit white light.

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 and a second light emitting part 550 including a second light emitting material layer 540 . and a third light emitting unit 570 including a third light emitting material layer 560 , and a first charge generating layer 580 positioned between the first light emitting unit 530 and the second light emitting unit 550 , and , and a second charge generation layer 590 positioned between the second light emitting unit 550 and the third light emitting unit 570 .

The first charge generating layer 580 is positioned between the first and second light emitting units 530 and 550 , and the second charge generating layer 590 is positioned between the second and third light emitting units 550 and 570 . do. That is, the first light emitting unit 530 , the first charge generating layer 580 , the second light emitting unit 550 , the second charge generating layer 590 , and the third light emitting unit 570 are formed by the first electrode 460 . are sequentially stacked on top. That is, the first light emitting unit 530 is positioned between the first electrode 460 and the first charge generating layer 580 , and the second light emitting unit 550 is provided with the first and second charge generating layers 580 and 590 . ), and the third light emitting part 570 is positioned between the second charge generating layer 590 and the second electrode 464 .

The first light emitting part 530 includes a hole injection layer 532 , a first hole transport layer 534 , a first electron blocking layer 536 , and a first light emitting material layer 520 sequentially stacked on the first electrode 460 . ), a first hole blocking layer 538 may be included. For example, the hole injection layer 532 , the first hole transport layer 534 , and the first electron blocking layer 536 are sequentially positioned between the first electrode 460 and the first light emitting material layer 520 , and the first The hole blocking layer 538 may be positioned between the first light emitting material layer 520 and the first charge generating layer 580 .

The first light-emitting material layer 520 includes the light-emitting compound represented by 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 Formula 4 .

The first light emitting material layer 520 may further include a second compound 524 . For example, the second compound 524 may be one of the compounds represented by Formula 5 and represented by Formula 6.

In this case, 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 is 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 wt%. In order to realize sufficient efficiency and lifespan, the first compound 522 may have about 0.1 to 10 wt%, preferably about 1 to 5 wt%.

The first electron blocking layer 536 may include the compound represented by Chemical Formula 7 as an electron blocking material. Also, the first hole blocking layer 538 may include at least one of a compound of Formula 9 and a compound of Formula 11-1 or Formula 11-2 as a hole blocking material.

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 positioned between the first charge generating layer 580 and the second light emitting material layer 540, and the electron transport layer 554 is formed between the second light emitting material layer 540 and the second charge generating layer ( 590) is located between

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.

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

In addition, the second light emitting material layer 540 may have a triple-layer structure of a first layer including a host and a red dopant, a second layer including a host and a yellow-green dopant, and a third layer including a host and a green dopant. have.

The third light emitting unit 570 includes 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 . may include

The third light emitting material layer 560 includes the light emitting compound represented by 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 Formula 4 .

The third light emitting material layer 560 may further include a fourth compound 564 . For example, the fourth compound 564 may be one of the compounds represented by Formula 5 and represented by Formula 6.

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 is 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 wt%. In order to realize sufficient efficiency and lifespan, the third compound 562 may have about 0.1 to 10% by weight, preferably about 1 to 5% by weight.

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 . Also, the weight ratio of the first compound 522 in the first light emitting material layer 520 to the weight ratio of the third compound 562 in the third light emitting material layer 560 may be the same or different.

The second electron blocking layer 574 may include the compound represented by Chemical Formula 7 as an electron blocking material. In addition, the second hole blocking layer 576 may include at least one of a compound of Formula 9 and a compound of Formula 11-1 or Formula 11-2 as a hole blocking material.

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

In the first charge generation layer 580 , an 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 an N type It is located between the charge generation layer 582 and the second hole transport layer 552 .

In the second charge generation layer 590 , the N-type charge generation layer 592 is positioned between the electron transport layer 454 and the third hole transport layer 572 , and the P-type charge generation layer 594 is an N-type charge generation layer It is located between 592 and the third hole transport layer 572 .

In the organic light emitting diode (D), each of the first and third light emitting material layers 520 and 560 includes the light emitting compound 242 of Formula 1, respectively, and thus the organic light emitting diode (D) and the organic light emitting display device The lifetime of (100) is greatly improved.

In addition, the organic light emitting diode D including the first and third light emitting units 530 and 570 and the second light emitting unit 550 for emitting yellow-green or red/green light may emit white light.

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 an additional light emitting unit and a charge generating layer.

Referring back to FIG. 5 , the second electrode 464 is formed on the first substrate 410 on which the organic emission layer 462 is formed.

In the organic light emitting display device 400 of the present invention, since light emitted from the organic light emitting layer 462 is incident on the color filter layer 480 through the second electrode 464, the second electrode 464 can transmit the light. so that it has a thin thickness.

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

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

Although not shown, 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).

Although not shown, in order to prevent external moisture from penetrating into the organic light emitting diode (D), an encapsulation film may be formed. 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.

In addition, a polarizing plate for reducing external light reflection may be attached to the outer surface of the second substrate 470 . For example, the polarizing plate may be a circular polarizing plate.

In the organic light emitting diode (D) of FIG. 5 , the first electrode 460 is a reflective electrode, the second electrode 464 is a transmissive (semi-transmissive) electrode, and the color filter layer 480 is an upper portion of the organic light emitting diode (D). is being placed on Alternatively, the first electrode 460 may be a transmissive (semi-transmissive) electrode and the second electrode 464 may be a reflective electrode. In this case, the color filter layer 480 includes the organic light emitting diode D and the first substrate 410 . ) can be placed between

In addition, 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 may 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. Accordingly, the color purity of the organic light emitting display device 400 may be further improved.

Also, a color conversion layer may be included instead of the color filter layer 480 .

As described above, in the organic light emitting diode display 400 , the organic light emitting diodes D of the red pixel RP, the green pixel GP, and the blue pixel BP emit white light, and the organic light emitting diode D ), the light passes through the red color filter 482 , the green color filter 484 , and the blue color filter 486 , so that the red pixel RP, the green pixel GP, and the blue pixel BP are green and red. and blue, respectively.

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

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

As shown in FIG. 8 , the organic light emitting diode display 600 includes a first substrate 610 on which a red pixel RP, a green pixel GP, and a blue pixel BP are defined, and a first substrate 610 . a second substrate 670 facing the A color conversion layer 680 positioned between the substrates 670 is included.

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

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.

A thin film transistor Tr is provided on the first substrate 610 to correspond to each of the red pixel RP, the green pixel GP, and the blue pixel BP, and one electrode of the thin film transistor Tr, for example, a drain A protective layer 650 having a drain contact hole 652 exposing an electrode is formed to cover the thin film transistor Tr.

An organic light emitting diode D including a first electrode 660 , an organic light emitting layer 662 , and a second electrode 664 is formed on the passivation layer 650 . In this case, the first electrode 660 may be connected to the drain electrode of the thin film transistor Tr through the drain contact hole 652 .

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

In this case, the organic light emitting diode D has the structure of FIG. 3 or 4 and may emit blue light. That is, the organic light emitting diode D is provided in each of the red pixel RP, the green pixel GP, and the blue pixel BP to provide blue light.

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

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

In the red pixel RP, the blue light from the organic light emitting diode D is converted into red light by the first color conversion layer 682, and the blue light from the organic light emitting diode D in the green pixel GP is It is converted into green light by the second color conversion layer 684 .

Accordingly, the organic light emitting display device 600 may implement a color image.

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 . have.

Although the above has been described with reference to the preferred embodiment of the present invention, those skilled in the art can variously modify and change the present invention within the scope without departing from the spirit and scope of the present invention described in the claims below You will understand that it can be done.

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: light emitting material layer
242, 322, 342, 522, 562, 722: first compound (luminescent body)
D: organic light emitting diode

Claims (15)

represented by the formula (1),
n is 0 or 1, X is one of B, P=O, P=S,
each of Y ₁ and Y ₂ is independently one of NR ₁ , C(R ₂ ) ₂ , O, S, Se, Si(R ₃ ) ₂ , Y ₃ is O or S;
Each of R ₁ to R ₃ is independently hydrogen, deuterium, a C1 to C10 alkyl group unsubstituted or substituted with deuterium, a C6 to C30 arylamine group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, unsubstituted or It is selected from a C6 to C30 aryl group substituted with deuterium or a C1 to C10 alkyl group, a C5 to C30 heteroaryl group unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group,
each of R ₄ to R ₇ is independently hydrogen, deuterium, a C1 to C10 alkyl group unsubstituted or substituted with deuterium, a C6 to C30 arylamine group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, unsubstituted or a C6 to C30 aryl group substituted with deuterium or a C1 to C10 alkyl group, a C5 to C30 heteroaryl group unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group, or adjacent two are connected to each other to form a ring,
each of R ₈ and R ₉ is independently hydrogen, deuterium, a C1 to C10 alkyl group unsubstituted or substituted with deuterium, a C6 to C30 arylamine group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, unsubstituted or A C6 to C30 aryl group substituted with deuterium or a C1 to C10 alkyl group, a C5 to C30 heteroaryl group unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group, or connected to each other to form a ring,
A light-emitting compound, characterized in that each of ring A and E ring is independently selected from a substituted or unsubstituted 6 membered cycloalkyl ring, a substituted or unsubstituted 6 membered aromatic ring, and a substituted or unsubstituted heteroaromatic ring.
[Formula 1]

The method of claim 1,
Formula 1 is a light emitting compound, characterized in that represented by Formula 2-1.
[Formula 2-1]

3. The method of claim 2,
Formula 2-1 is represented by Formula 2-2,
In Formula 2-2, each of R ₂₁ to R ₂₇ is independently hydrogen, deuterium, an unsubstituted or deuterium-substituted C1 to C10 alkyl group, unsubstituted or deuterium or a C1 to C10 alkyl group substituted with a C6 to C30 alkyl group. An arylamine group, a C6 to C30 aryl group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, a C5 to C30 heteroaryl group unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group, characterized in that a luminescent compound.
[Formula 2-2]

The method of claim 1,
Formula 1 is a light-emitting compound, characterized in that represented by Formula 3-1.
[Formula 3-1]

5. The method of claim 4,
Formula 3-1 is represented by Formula 3-2,
In Formula 3-2, each of R ₃₁ to R ₃₇ is independently hydrogen, deuterium, an unsubstituted or deuterium-substituted C1 to C10 alkyl group, unsubstituted or deuterium or a C1 to C10 alkyl group substituted with a C6 to C30 alkyl group. An arylamine group, a C6 to C30 aryl group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, a C5 to C30 heteroaryl group unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group, characterized in that a luminescent compound.
[Formula 3-2]

5. The method of claim 4,
Formula 3-1 is represented by Formula 3-3,
In Formula 3-3, Y ₄ is one of NR ₁ , C(R ₂ ) ₂ , O, S, Se, Si(R ₃ ) ₂ , and each of R ₁₀ to R ₁₃ is independently hydrogen, deuterium, substituted C1 to C10 alkyl group unsubstituted or substituted with deuterium, C6 to C30 arylamine group unsubstituted or substituted with deuterium or C1 to C10 alkyl group, C6 to C30 unsubstituted or substituted with deuterium or C1 to C10 alkyl group An aryl group, unsubstituted or deuterium, or a C5 to C30 heteroaryl group substituted with a C1 to C10 alkyl group or adjacent two are connected to each other to form a ring, and R ₁₄ and R ₁₅ are each independently hydrogen, deuterium, unsubstituted C1 to C10 alkyl group unsubstituted or substituted with deuterium, C6 to C30 arylamine group unsubstituted or substituted with deuterium or C1 to C10 alkyl group, C6 to C30 aryl unsubstituted or substituted with deuterium or C1 to C10 alkyl group A light-emitting compound, characterized in that it is selected from a C5 to C30 heteroaryl group substituted with a group, unsubstituted or deuterium or a C1 to C10 alkyl group, or is linked to each other to form a ring.
[Formula 3-3]

7. The method of claim 6,
Formula 3-3 is represented by Formula 3-4,
In Formula 3-4, each of R ₄₁ to R ₄₃ is independently hydrogen, deuterium, unsubstituted or substituted C1 to C10 alkyl group, unsubstituted or deuterium or C1 to C10 alkyl group substituted with C6 to C30 alkyl group An arylamine group, a C6 to C30 aryl group unsubstituted or substituted with deuterium or a C1 to C10 alkyl group, a C5 to C30 heteroaryl group unsubstituted or substituted with a deuterium or a C1 to C10 alkyl group, characterized in that a luminescent compound.
[Formula 3-4]

The method of claim 1,
The light-emitting compound is a light-emitting compound, characterized in that it is one of the compounds of formula (4).
[Formula 4]

a substrate;
a first electrode; a second electrode facing the first electrode; An organic light emitting diode including a first light emitting material layer comprising a first compound and positioned between the first electrode and the second electrode and positioned on the substrate,
The first compound is an organic light emitting diode of any one of claims 1 to 8, wherein the light emitting compound.
10. The method of claim 9,
The first light-emitting material layer further comprises a second compound,
The second compound is represented by Formula 5,
In Formula 4, Ar ₁ and Ar ₂ are each independently a C ₆ -C ₃₀ aryl group or a C ₅ -C ₃₀ heteroaryl group, L is a single bond or a C ₆ -C ₂₀ arylene group, and hydrogen is unsubstituted Or an organic light emitting device, characterized in that some or all are substituted with deuterium.
[Formula 5]

10. The method of claim 9,
The organic light emitting diode,
a second light emitting material layer including a third compound and positioned between the first light emitting material layer and the second electrode;
Further comprising a first charge generation layer positioned between the first light-emitting material layer and the second light-emitting material layer,
The third compound is an organic light emitting device, characterized in that represented by the formula (1).
10. The method of claim 9,
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 a color conversion layer provided between the substrate and the organic light emitting diode or on the organic light emitting diode corresponding to the red pixel and the green pixel.
12. The method of claim 11,
The organic light emitting diode includes a third light emitting material layer positioned between the first charge generating layer and the second light emitting material layer, and a second charge positioned between the second light emitting material layer and the third light emitting material layer. further comprising a generative layer,
and the third light emitting material layer emits yellow-green light or red and green light.
10. The method of claim 9,
The organic light emitting diode includes a second light emitting material layer emitting yellow-green light and positioned between the first light emitting material layer and the second electrode, and a second light emitting material layer positioned between the first light emitting material layer and the second light emitting material layer. 1 Organic light emitting device, characterized in that it further comprises a charge generation layer.
14. The method of claim 13,
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 a color filter layer provided between the substrate and the organic light emitting diode or above the organic light emitting diode to correspond to the red pixel, the green pixel, and the blue pixel.

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