KR102635702B1 - Organic light emitting diode, organic light emitting display device and compound therefor - Google Patents

Abstract

The present invention discloses an organic light emitting device and an organic light emitting display device including the same. The organic light emitting device according to the present invention and the organic light emitting display device including the same include a first electrode disposed on a substrate, a second electrode disposed to face the first electrode, and disposed between the first electrode and the second electrode. and an organic light-emitting layer including a first organic light-emitting layer disposed in the first subpixel, a second organic light-emitting layer disposed in the second subpixel, and a third organic light-emitting layer disposed in the third subpixel, and the first electrode. and a hole transport layer disposed between the organic light emitting layer and between the hole transport layer and the organic light emitting layer, a first light emitting auxiliary layer disposed in the first subpixel, a second light emitting auxiliary layer disposed in the second subpixel, and It is disposed on the first and second light emitting auxiliary layers between the hole transport layer and the organic light emitting layer and includes a third light emitting auxiliary layer commonly disposed in the first to third subpixels.

Description

Organic light emitting device, organic light emitting display device and compound for organic light emitting device {ORGANIC LIGHT EMITTING DIODE, ORGANIC LIGHT EMITTING DISPLAY DEVICE AND COMPOUND THEREFOR }

The present invention relates to organic light emitting devices and organic light emitting display devices including the same.

In an organic light emitting device, holes introduced from the anode and electrons introduced from the cathode recombine in the organic light emitting layer sandwiched between the anode and the cathode to create molecular excitons with a high energy excited state. It is a light-emitting device that emits light unique to the material as it returns to the low-energy ground state after being formed.

These organic light-emitting devices are devices that use materials that emit light when a voltage is applied, and have the advantages of high brightness, excellent contrast, multicolor, large viewing angle, high response speed, and low driving voltage.

Meanwhile, an organic light emitting display device that displays an image is composed of a plurality of pixels, each containing an organic light emitting element. At this time, each pixel may be composed of two or more light-emitting areas, for example, a red light-emitting area, a green light-emitting area, and a blue light-emitting area.

Despite the above-described advantages of such organic light emitting display devices, there is a problem in that organic light emitting elements arranged in each light emitting area have a short lifespan or low efficiency. In addition, there are difficulties in the manufacturing process in patterning each pixel for each light-emitting area to increase the area.

Accordingly, there is a need for an organic light emitting display device that can reduce the number of times patterning the light emitting regions in the manufacturing process of an organic light emitting display device while improving the light emitting performance of organic light emitting elements or at least maintaining the same performance as before.

The purpose of the present invention is to provide an organic light emitting device that improves light emitting performance and an organic light emitting display device including the organic light emitting device.

Additionally, an object of the present invention is to provide an organic light emitting device and an organic light emitting display device including the organic light emitting device that minimizes the patterning process of light emitting areas during manufacturing.

In one aspect, the organic light emitting device according to the present invention includes a first electrode disposed on a substrate, a second electrode disposed to face the first electrode, disposed between the first electrode and the second electrode, and the first electrode. An organic light-emitting layer including a first organic light-emitting layer disposed in the first subpixel, a second organic light-emitting layer disposed in the second subpixel, and a third organic light-emitting layer disposed in the third subpixel, between the first electrode and the organic light-emitting layer A hole transport layer disposed in and between the hole transport layer and the organic light emitting layer, a first light emitting auxiliary layer disposed in the first subpixel, a second light emitting auxiliary layer disposed in the second subpixel, the hole transport layer and the organic light emitting layer. It includes a third auxiliary light emitting layer disposed on the first and second auxiliary light emitting layers between the light emitting layers and commonly disposed in the first to third subpixels.

In another aspect, the organic light emitting device according to the present invention includes a substrate including two or more subpixels, a first electrode disposed on the substrate, a second electrode disposed to face the first electrode, the first electrode and Organic light emitting layers of different colors disposed in each of two or more subpixels between the second electrodes, a hole transport layer disposed between the first electrode and the organic light emitting layer, and disposed between the hole transport layer and the organic light emitting layer, the two It includes one or more individual light-emitting auxiliary layers respectively disposed in some of the above subpixels, and a common light-emitting auxiliary layer disposed on the individual light-emitting auxiliary layers and commonly disposed in two or more subpixels.

In another aspect, the organic light emitting display device according to the present invention includes a driving transistor disposed in each of the first subpixel, the second subpixel, and the third subpixel that emit different colors, and is electrically connected to the driving transistor and a substrate. a first electrode disposed on the first electrode, a second electrode disposed to face the first electrode, a first organic light-emitting layer disposed between the first electrode and the second electrode and disposed in the first subpixel, and An organic light-emitting layer including a second organic light-emitting layer disposed in the second subpixel, a third organic light-emitting layer disposed in the third subpixel, a hole transport layer disposed between the first electrode and the organic light-emitting layer, and between the hole transport layer and the organic light-emitting layer. is disposed on the first and second light-emitting auxiliary layers between the first sub-pixel, the second light-emitting auxiliary layer and the second sub-pixel, and the hole transport layer and the organic light-emitting layer. and includes a third auxiliary light emitting layer commonly disposed in the first to third subpixels.

The organic light emitting device according to the present invention and the organic light emitting display device including the same have the effect of improving the lifespan and efficiency of the organic light emitting device.

In addition, the organic light emitting device according to the present invention and the organic light emitting display device including the same have the effect of minimizing the patterning process of the light emitting areas during manufacturing.

Figure 1 is a cross-sectional view of an organic light-emitting device according to an embodiment.
Figure 2 is a diagram showing the thickness of light-emitting auxiliary layers of an organic light-emitting device according to an embodiment.
Figure 3 is a diagram showing HOMO levels of a hole transport layer and a light-emitting auxiliary layer in an organic light-emitting device according to an embodiment.
Figure 4 is a cross-sectional view of an organic light-emitting device according to a comparative example.
Figures 5a to 5g are diagrams showing a method of manufacturing an organic light emitting device according to an embodiment of the present invention.
Figure 6 is a cross-sectional view of an organic light emitting device according to another embodiment.
Figure 7 is a conceptual diagram of an organic light emitting display device to which embodiments can be applied.
FIG. 8 is a diagram showing the pixel structure of the organic light emitting display panel of FIG. 7.

Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. The embodiments introduced below are provided as examples so that the idea of the present invention can be sufficiently conveyed to those skilled in the art. Accordingly, the present invention is not limited to the embodiments described below and may be embodied in other forms. And in the drawings, the size and thickness of the device may be exaggerated for convenience. Like reference numerals refer to like elements throughout the specification.

The advantages and features of the present invention and methods for achieving them will become clear by referring to the embodiments described in detail below along with the accompanying drawings. However, the present invention is not limited to the embodiments disclosed below and will be implemented in various different forms, but the present embodiments only serve to complete the disclosure of the present invention and are within the scope of common knowledge in the technical field to which the present invention pertains. It is provided to fully inform those who have the scope of the invention, and the present invention is only defined by the scope of the claims. Like reference numerals refer to like elements throughout the specification. The sizes and relative sizes of layers and regions in the drawings may be exaggerated for clarity of explanation.

When an element or layer is referred to as another element or “on” or “on” it includes not only those directly on top of another element or layer, but also all cases where there is another layer or element in between. do. On the other hand, referring to an element as “directly on” or “directly on” indicates that there is no intervening element or layer.

Spatially relative terms such as “below, beneath,” “lower,” “above,” and “upper” refer to one element or component as shown in the drawing. It can be used to easily describe the correlation with other elements or components. Spatially relative terms should be understood as terms that include different directions of the element during use or operation in addition to the direction shown in the drawings. For example, if an element shown in the drawings is turned over, an element described as “below” or “beneath” another element may be placed “above” the other element. Accordingly, the illustrative term “down” can include both downward and upward directions.

Additionally, when describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are only used to distinguish the component from other components, and the nature, sequence, order, or number of the components are not limited by the term.

Figure 1 is a cross-sectional view of an organic light-emitting device according to an embodiment. Referring to FIG. 1, the organic light emitting device 200 according to one embodiment includes a first subpixel (SP1), a second subpixel (SP3), and a third subpixel that emit different colors on the substrate 100. Includes (SP3).

The substrate 100 may be a substrate used in a typical organic light emitting device. The substrate 100 may be made of glass or transparent plastic, and may also be made of a translucent or opaque material such as silicon or stainless steel.

The first subpixel (SP1), the second subpixel (SP2), and the third subpixel (SP3) may be a red (R) subpixel, a green (G) subpixel, and a blue (B) subpixel, respectively. For example, the red (R) subpixel, green (G) subpixel, and blue (B) subpixel constitute each pixel (P) of the organic light emitting display device 1000, as described with reference to FIG. 9. You can.

Meanwhile, the organic light emitting device 200 includes a first electrode 120 disposed on a substrate 100, a second electrode 180 disposed to face the first electrode 120, and the first electrode 120. ) and an organic light-emitting layer 145 disposed between the second electrode 180. At this time, the first electrode 120 may be an anode and the second electrode 180 may be a cathode, but embodiments of the present invention are not limited thereto.

For example, in the case of the inverted type, the first electrode 120 may be a cathode and the second electrode 180 may be an anode. However, in the embodiments described later, the description will focus on the configuration in which the first electrode 120 of the organic light-emitting device 200 is an anode and the second electrode 170 is a cathode.

The first electrode 120 may be disposed separately for each subpixel on the insulating film 111 of the substrate 100. The first electrode 120 disposed in each subpixel is electrically connected to either the source or drain 110 of the transistor including the source, drain, gate, and active layer through a contact hole formed in the insulating film 111. .

The first electrode 120 may be made of a material with a relatively high work function. The first electrode 120 is, for example, ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), AZO (Al-doped zinc oxide), In2O3 (indium oxide), or SnO 2 (tin). oxide), but is not limited thereto. The first electrode 120 can be formed through a deposition method or sputtering method.

The second electrode 180 may be made of a metal, alloy, electrically conductive compound, or a mixture of two or more thereof having a relatively low work function. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. A transmissive electrode can be obtained by forming it into a thin film. Meanwhile, various modifications may be made to the embodiments of the present invention, such as forming a transmissive electrode using ITO or IZO to obtain a top emitting device.

The organic light emitting layer 145 is disposed in a first subpixel (eg, red (R) subpixel) and a second subpixel (eg, green (G) subpixel). It may include a second organic light emitting layer 145G and a third organic light emitting layer 145B disposed in a third subpixel (for example, a blue (B) subpixel).

At this time, the wavelength of the emitted light is larger in that order: the first organic light-emitting layer 145R, the second organic light-emitting layer 145G, and the third organic light-emitting layer 145B. Specifically, the first organic emission layer 145R may be a red organic emission layer, the second organic emission layer 145G may be a green organic emission layer, and the third organic emission layer 145B may be a blue organic emission layer.

At this time, the first organic emission layer 145R may include a red host and a red dopant. The red host may use Alq 3, CBP, PVK, ADN, TCTA, TPBI, TBADN, E3, DSA, or a mixture of two or more thereof, but is not limited thereto.

As red dopants, PtOEP, Ir(piq)3, Btp2Ir(acac), Ir(piq)2(acac), Ir(2-phq)2(acac), Ir(2-phq)3, Ir(flq)2( Compounds containing acac), Ir(fliq)2(acac), DCM or DCJTB can be used, but are not limited thereto.

The second organic emission layer 145G may include a green host and a green dopant. The green host may use Alq 3, CBP, PVK, ADN, TCTA, TPBI, TBADN, E3, DSA, or a mixture of two or more thereof, but is not limited thereto.

As green dopants, Ir(ppy) 3 (tris(2-phenylpyridine) iridium, tris(2-phenylpyridine) iridium), Ir(ppy) 2(acac)(Bis(2-phenylpyridine)(Acetylacetonato)iridium(III), Bis(2-phenylpyridine)(acetylaceto)iridium(III)), Ir(mppy)3 (tris(2-(4-tolyl)phenylpiridine)iridium, tris(2-(4-tolyl)phenylpyridine)iridium) , C545T (10-(2benzothiazolyl)-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-[1]benzopyrano [6,7,8-ij]-quinolizin11 -one, 10-(2-benzothiazolyl)-1,1,7,7-tetramethyl-2,3,6,7,-tetrahydro-1H,5H,11H-[1]benzopyrano [6 ,7,8ij]-quinolizin-11-one), etc. may be used, but are not limited thereto.

The first organic emission layer 145R and the second organic emission layer 145G may be formed using methods such as vacuum deposition, spin coating, casting, and LB methods. Meanwhile, a codeposition method may be used to form the first organic emission layer 145R and the second organic emission layer 145G including a host and a dopant.

The third organic emission layer 145B may include a blue host and a blue dopant. For example, the blue host is Alq3, CBP(4,4'-N,N'-dicabazole-biphenyl, 4,4'-N,N'-dicabazole-biphenyl), PVK(poly(n-vinylcabazole ), poly (n-vinylcarbazole)), ADN(9,10-di(naphthalene-2-yl)anthracene, 9,10-di(naphthalene-2-yl)anthracene), TCTA, TPBI(1, 3,5-tris(N-phenylbenzimidazole-2-yl)benzene, 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene), TBADN(3-tert-butyl-9,10- di(naphth-2-yl) anthracene, 3-tert-butyl-9,10-di(naphth-2yl) anthracene), E3, DSA (distyrylarylene), or mixtures of two or more thereof. However, it is not limited to this.

As blue dopants, F2Irpic, (F2ppy)2Ir(tmd), Ir(dfppz)3, ter-fluorene, DPAVBi(4,4'-bis(4diphenylaminostyryl)biphenyl, 4,4'-bis (4) Compounds including -diphenylaminostaryl) biphenyl), TBPe (2,5,8,11-tetra-tbutylperylene, 2,5,8,11-tetra-ti-butyl perylene), etc. can be used. , but is not limited to this.

The third organic light-emitting layer 145B can be formed using a method such as vacuum deposition, spin coating, casting, or LB method. When forming a light-emitting layer using vacuum deposition or spin coating, deposition conditions vary depending on the compound used, but can generally be selected from a range of conditions that are almost the same as those for forming the hole injection layer. Meanwhile, a co-deposition method may be used to simultaneously form a layer containing a host and a dopant.

The organic light emitting device 200 includes a hole transport layer 135 disposed between the first electrode 120 and the organic light emitting layer 145, and a light emitting auxiliary layer disposed between the hole transport layer 135 and the organic light emitting layer 145 ( 140) may be included.

Meanwhile, the light-emitting auxiliary layer 140 includes a first light-emitting auxiliary layer (140R'), a second light-emitting auxiliary layer (140G'), and a third light-emitting auxiliary layer (140B') disposed on the hole transport layer 135. Includes. Specifically, the first auxiliary light emitting layer 140R' is disposed on the hole transport layer 135 in the first subpixel SP1, and the second auxiliary light emitting layer 140G' is disposed on the second sub pixel SP1. It is disposed on the hole transport layer 130 in the pixel SP2.

In addition, the third auxiliary light emitting layer 140B' is formed by forming a first auxiliary light emitting layer 140R' and a second auxiliary light emitting layer 140G' in the first subpixel SP1 and the second subpixel SP2, respectively. It is disposed on the hole transport layer 135 in the third subpixel SP3. That is, the third auxiliary light emitting layer 140B' is commonly disposed in the first subpixel SP1, the second subpixel SP2, and the third subpixel SP3.

Meanwhile, the first light-emitting auxiliary layer 140R', the second light-emitting auxiliary layer 140G', and the third light-emitting auxiliary layer 140B' may play a hole transport role, for example, and may be made of a hole transport material. there is. The first light-emitting auxiliary layer (140R'), the second light-emitting auxiliary layer (140G'), and the third light-emitting auxiliary layer (140B') may be made of the same material or compound or may be made of different materials or compounds. In addition, the first light-emitting auxiliary layer 140R', the second light-emitting auxiliary layer 140G', and the third light-emitting auxiliary layer 140B' may be made of the same material or compound as the hole transport layer 135, or may be made of different materials or compounds. It may be composed of compounds.

For example, the hole transport layer 135, the first light-emitting auxiliary layer (140R'), and the second light-emitting auxiliary layer (140G') are made of a material containing a tertiary amine or a tertiary amine containing fluorine. It can be done.

Specifically, the hole transport layer 135, the first light-emitting auxiliary layer (140R'), and the second light-emitting auxiliary layer (140G') may include a compound represented by the following formula (1).

[Formula 1]

In Formula 1, L is a single bond, a C6-C60 arylene group, a fluorenylene group, or a C2-C60 heterocyclic group, l and m are integers of 0 or more, and R ₁ and R ₂ are C6- Any one of an aryl group at C60, a heterocyclic group at C2-C60, or an alkenyl group, Ar ₁ and Ar ₂ is any one of a C6-C60 aryl group, a C2-C60 heterocyclic group, or a fluorene group, and X may be either NR' or CR'R''. In this specification, the fluorene group includes a spirofluorene group.

Here, R' and R" are either a C6-C60 aryl group, a C2-C60 heterocyclic group, or a C1-C30 alkyl group.

Here, Ar ₁ And when Ar ₂ is a C2-C60 heterocyclic group, it may include carbazole.

In Formula 1, R' and R'' of X can combine with each other to form a spiro compound.

When l and m in R ₁ and R ₂ are integers of 1 or more, R ₁ and R ₂ can be combined with each other to form a ring.

The aryl group, heterocyclic group, alkenyl group, alkyl group, aryloxy group, fluorene group (including spirofluorene group), arylene group, and fluorenyl group (including spirofluorenyl group) are C6-24 aryl groups. , C2-24 heterocyclic group, C1-30 alkyl group, C2-24 alkenyl group, C6-24 aryloxy group, fluorenyl group, halogen group, nitro group, and at least one selected from the group consisting of cyano group. It may be further substituted with a substituent, and when each of these substituents is adjacent, they may combine with each other to form a ring.

Additionally, Formula 1 may include compounds represented by Formulas 2 to 4 below. That is, the hole transport layer 135, the first light-emitting auxiliary layer (140R'), and the second light-emitting auxiliary layer (140G') may include compounds represented by Formulas 2 to 4 below. At this time, the first light-emitting auxiliary layer (140R') and the second light-emitting auxiliary layer (140G') may be the same compound, and the hole transport layer 135 may be a different compound, but is not limited thereto.

[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4, L is any one of a C6-C60 arylene group, a fluorene group, and a C2-C60 heterocyclic group, and Ar ₃ and Ar ₄ is any one of a C6-C60 aryl group, a C2-C60 heterocyclic group, and a fluorene group, and Ar ₅ to Ar ₈ are any one of a C6-C60 aryl group, a C2-C60 heterocyclic group, and a fluorene group, and R' and R” are a C6-C60 aryl group, a C2-C60 heterocyclic group, or C1- It is one of the alkyl groups of C30.

Here, Ar ₃ And when Ar ₄ is a C2-C60 heterocyclic group, carbazole may be included, and when Ar ₅ to Ar ₈ are C6-C60 heterocyclic groups, carbazole may not be included.

Additionally, the hole transport layer 135 may include a compound represented by Chemical Formula 2. Meanwhile, when the hole transport layer 135 includes a compound represented by Formula 2, the first light-emitting auxiliary layer 140R' and the second light-emitting auxiliary layer 140G' are represented by Formulas 3 and 4. It may contain compounds.

At this time, as described above, the first light emitting auxiliary layer 140R' and the second light emitting auxiliary layer 140G' may be the same compound, and the hole transport layer 135 may be a different compound. The hole transport layer 135, the first light-emitting auxiliary layer 140R', and the second light-emitting auxiliary layer 140G' may use the same compounds represented by the above-described chemical formulas 1 to 4.

Additionally, the third auxiliary light emitting layer 140B' may include a compound represented by the following Chemical Formula 5.

[Formula 5]

In Formula 5, 1) R ₃ and R ₄ are hydrogen, deuterium, C6-60 aryl group, C2-60 alkenyl group, C1-60 alkyl group, C6-60 aryloxy group, C2-60 hetero group. Cyclic group, cyano group, nitro group, halogen group.

2) n=0-4 integer, o=0-3 integer

3) L is a single bond, an arylene group at C6-60, a heterocyclic group at C3-60,

4) Ar ₉ and Ar ₁₀ are an aryl group at C6-24, a heterocyclic group at C3-24, and a fluorenyl group.

5) When n=2 or more, R ₃ can combine with each other to form a ring, and when o=2 or more, R ₄ can combine with each other to form a ring.

The aryl group, heterocyclic group, alkenyl group, alkyl group, aryloxy group, arylene group, and fluorenyl group (including spirofluorenyl group) include an aryl group at C6-24, a heterocyclic group at C2-24, and a heterocyclic group at C1-30. may be further substituted with one or more substituents selected from the group consisting of alkyl group, C2-24 alkenyl group, C6-24 aryloxy group, fluorenyl group, halogen group, nitro group, and cyano group, and each of these substituents When adjacent, they can combine with each other to form a ring.

Additionally, Formula 5 may include compounds represented by Formulas 6 and 7 below. That is, the third auxiliary light emitting layer 140B' may include compounds represented by the following Chemical Formulas 6 to 9.

[Formula 6]

[Formula 7]

In Formulas 6 and 7, R ₃ and R ₄ , n, o, L, Ar ₉ , and Ar ₁₀ are the same as Formula 5.

Generally, when the organic light-emitting layer is phosphorescent, the material for the light-emitting auxiliary layer is a material with a high T1 value, whereas when the organic light-emitting layer is fluorescent, the lifespan tends to be shortened when a phosphorescent light-emitting auxiliary layer is used. However, in the case of the compounds represented by the above-mentioned formulas 5 to 7, it can be confirmed that both blue, where the organic light-emitting layer is fluorescent, and green and red, where the organic light-emitting layer is phosphorescent, exhibit a high lifespan even when a common auxiliary light emitting layer is used. In addition, it can be confirmed that it shows high efficiency in green and red phosphorescence.

When the above-described substituent in Formulas 1 to 7 is a fluorene group or a fluorene group, it may include a spirofluorene group or a spirofluorene group.

Here, in the case of the aryl group, the aryl group may have 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, and more preferably 6 to 30 carbon atoms. In the case of the heterocyclic group, the aryl group may have 2 to 60 carbon atoms, preferably 2 carbon atoms. It may be a heterocycle with ~30 carbon atoms, more preferably 2-20 carbon atoms, and in the case of the alkyl group, it may be an alkyl group with 1-30 carbon atoms, more preferably 1-20 carbon atoms, and preferably 1-10 carbon atoms.

More specifically, the compounds represented by Formulas 1 to 7 may be any one of the following compounds, and are not limited to the following compounds.

Hereinafter, examples of synthesis of compounds represented by Formulas 1 to 7 and examples of manufacturing organic electric devices according to the present invention will be described in detail through examples, but the present invention is not limited to the examples below.

[ Synthesis example ]

Compounds represented by formulas 1 and 2 according to the present invention (final product (1), for example, compounds represented by P1-1 to P1-77) are prepared by reacting Sub 1 and Sub 4 as shown in Scheme 1 below. However, it is not limited to this.

I. Final product (1)

<Scheme 1>

Example of synthesis of Sub 1 (when L is not a single bond)

Sub 4 of Scheme 1 can be synthesized through the reaction route of Scheme 2 below, but is not limited thereto. Specific compounds of Sub 1 may be compounds represented by the formulas Sub 1-1 to Sub 1-52, which will be described later, but are not limited thereto.

<Scheme 2>

(1) M 1-1 synthesis example

After dissolving 3-bromo-9-phenyl-9H-carbazole (45.1 g, 140 mmol) in 980mL of DMF, Bispinacolborate (39.1 g, 154 mmol), PdCl ₂ (dppf) catalyst (3.43 g, 4.2 mmol), and KOAc ( After adding 41.3 g, 420 mmol) in order and stirring for 24 hours to synthesize the borate compound, the obtained compound was separated through a silicagel column and recrystallization to obtain 35.2 g (68%) of the borate compound.

(2) M 1-2 synthesis example

40 g (64%) was obtained through the same experimental method as M 1-1.

(3) Sub 1-23 synthesis example

After dissolving M 1-1 (29.5 g, 80 mmol) in 360 mL of THF, 4-bromo-4'-iodo-1,1'-biphenyl (30.16 g, 84 mmol), Pd(PPh ₃ ) ₄ (2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol), and 180 mL of water were added, then stirred and refluxed. When the reaction was completed, extraction was performed with ether and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was recrystallized using a silicagel column to obtain 26.56 g (70%) of the product.

(4) Sub 1-16 synthesis example

M 1-2 (29.5 g, 80 mmol), THF 360 mL, 1-bromo-4-iodobenzene (23.8 g, 84 mmol), Pd(PPh ₃ ) ₄ (2.8 g, 2.4mmol), NaOH (9.6 g, 240 mmol), 180 mL of water, 22.9 g (72%) of product was obtained using the Sub 1-23 synthesis method above.

(5) Sub 1-26 synthesis example

After dissolving M 1-2 (29.5 g, 80 mmol) in 360 mL of THF, 4'-bromo-3-iodo-1,1'-biphenyl (30.16 g, 84 mmol), Pd(PPh ₃ ) ₄ (2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol), 180 mL of water, 24.7 g (65%) of the product was obtained using the Sub 1-23 synthesis method above.

(6) M 1-3 synthesis example

After dissolving 2-bromo-9-phenyl-9H-carbazole (45.1 g, 140 mmol) in 980mL of DMF, Bispinacolborate (39.1 g, 154 mmol), PdCl ₂ (dppf) catalyst (3.43 g, 4.2 mmol), and KOAc ( 41.3 g, 420 mmol) was used to obtain 36.2 g (70%) of the product using the M 1-1 synthesis method.

(7) M 1-4 synthesis example

43.6g (67%) was obtained through the same experimental method as M 1-1 above.

(8) Sub 1-32 synthesis example

After dissolving M 1-3 (30g, 81.24mmol) in 357mL of THF, 3-Bromoiodobenzene (22.98g, 81.24mmol), Pd(PPh ₃ ) ₄ (2.82g, 2.44mmol), NaOH (9.75g, 243.72mmol) , 26.95 g (70%) of the product was obtained using 179 mL of water using the Sub 1-23 synthesis method.

(9) Sub 1-28 synthesis example

M 1-3 (29.5 g, 80 mmol), THF 360 mL, 1-bromo-4-iodobenzene (23.8 g, 84 mmol), Pd(PPh ₃ ) ₄ (2.8 g, 2.4mmol), NaOH (9.6 g, After adding 240 mmol) and 180 mL of water, 23.26 g (73%) of the product was obtained through the same experimental method as in Sub 1-32 above.

(10) Sub 1-36 synthesis example

After dissolving M 1-3 (29.5 g, 79.89 mmol) in 351 mL of THF, 3,7-dibromodibenzo[b,d]thiophene (27.33 g, 79.89 mmol), Pd(PPh ₃ ) ₄ (1.38 g, 1.2 mmol) ), NaOH (4.79 g, 119.83 mmol), and 176 mL of water were added, and 25.79 g (64%) of the product was obtained through the same experimental method as Sub 1-32 above.

(11) Synthesis of Sub 1-47

1) M 1-I-47-I synthesis

After dissolving naphthalen-1-ylboronic acid (66g, 383.74mmol) in THF (1688ml) in a round bottom flask, 4-bromo-1-iodo-2-nitrobenzene (125.83g, 383.74mmol), Pd(PPh ₃ ) ₄ (13.30g, 11.51mmol), K ₂ CO ₃ (159.11g, 1151.23mmol), and water (844ml) were added, then stirred and refluxed. When the reaction was completed, extraction was performed with ether and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was recrystallized using a silicagel column to obtain 102.01 g (yield: 81%) of the product.

2) M 1-I-47-II synthesis

M 1-I-47-I (102g, 310.82mmol), Triphenylphosphine (203.81g, 777.04mmol), and o-Dichlorobenzene (1243ml) were added to the round bottom flask and refluxed at 180°C. When the reaction was completed, it was cooled to room temperature and extracted using methylene chloride and water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was recrystallized using a silicagel column to obtain 77.33 g of product (yield: 84%).

3) M 1-I-47 synthesis

After dissolving M 1-I-47-II (77.33g, 261.1mmol) in nitrobenzene (1305ml) in a round bottom flask, iodoben ene (58.59g, 287.21mmol), Na ₂ SO ₄ (37.09g, 261.1mmol), K ₂ CO ₃ (36.09g, 261.1mmol) and Cu (4.98g, 78.33mmol) were added and stirred at 200°C. When the reaction was completed, nitrobenzene was removed through distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 70.96 g of product (yield: 73%).

4) M 1-47 synthesis

After dissolving M 1-I-47 (70.96g, 216.82mmol) in 1084mL of DMF, Bispinacolborate (60.57g, 238.51mmol), PdCl ₂ (dppf) catalyst (4.76g, 6.50mmol), KOAc (63.84g, 650.47mmol) ) using the above M 1-1 synthesis method 64.55 (71%) of the products were obtained.

5) Sub 1-47 synthesis

After dissolving M 1-47 (64.55g, 153.94mmol) in THF (677ml) in a round bottom flask, 2,7-dibromo-9,9-dimethyl-9H-fluorene (54.20g, 153.94mmol), Pd(PPh) ₃ ) ₄ (2.67g, 2.31mmol), K ₂ CO ₃ (31.91g, 230.9mmol), and water (338ml) were used to obtain 59.96g of product (yield: 69) using the above M 1-I-47-I synthesis method. %) was obtained.

Although the synthesis method for some of the specific compounds of Sub 1 is exemplified, compounds represented by the formulas Sub 1-1 to Sub 1-52, which will be described later, can also be synthesized using the same synthesis method.

Synthesis example of Sub 4

Sub 4 of Scheme 1 can be synthesized through the reaction route of Scheme 3 below, but is not limited thereto. Specific compounds of Sub 4 may be compounds represented by formulas Sub 4-1 to Sub 1-81, which will be described later, but are not limited thereto.

<Scheme 3>

(1) Synthesis example of Sub 4-2

Aniline (15 g, 161.1 mmol), 1-bromonaphthalene (36.7 g, 177.2 mmol), Pd ₂ (dba) ₃ (7.37 g, 8.05 mmol), P(t-Bu) ₃ (3.26 g, 16.1 mmol) in a round bottom flask. mmol), NaOt-Bu (51.08 g, 531.5 mmol), and toluene (1690 mL) were added and the reaction was carried out at 100°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was recrystallized using a silicagel column to obtain 25.4 g of product. (Yield: 72%)

(2) Example of synthesis of Sub 4-9

After dissolving 4-bromo-1,1'-biphenyl (5.6g, 24mmol) in toluene, [1,1'-biphenyl]-4-amine (3.4g, 20mmol), Pd ₂ (dba) ₃ (0.5g) , 0.6mmol), P(t-Bu) ₃ (0.2g, 2mmol), NaO t -Bu (5.8g, 60mmol), and toluene (300 mL) were used to produce 6.2g of the product ( Yield: 80%) was obtained.

(3) Example of synthesis of Sub 4-30

In a round bottom flask, 4-Aminobiphenyl (15 g, 88.6 mmol), toluene (931 ml), 2-bromo-9,9-diphenyl-9H-fluorene (38.7 g, 97.5 mmol), Pd ₂ (dba) ₃ (4.1) g, 4.43 mmol), P( t -Bu) ₃ (1.8 g, 8.86 mmol), and NaO t -Bu (28.1 g, 292.5 mmol) were used to synthesize 30.6 g of product (yield: 71) using the Sub 4-2 synthesis method. %) was obtained.

Synthesis example of Sub 4-41

The starting material, 2-bromodibenzo[ b , d ]thiophene (9.57 g, 36.4 mmol), naphthalen-1-amine (10.41 g, 72.7 mmol), Pd ₂ (dba) ₃ (1 g, 1.1 mmol), 50% P ( t -Bu) ₃ (1.4ml, 2.9 mmol), NaO t -Bu (10.49 g, 109.1 mmol), and toluene were used to obtain 9.11 g of product (yield: 77%) using the Sub 4-2 synthesis method.

Synthesis example of Sub 4-77

[1,1'-biphenyl]- 3-amine (15g, 88.6mmol), Pd ₂ (dba) ₃ (4.1g, 4.43mmol), P( t -Bu) ₃ (1.8g, 8.9mmol), NaO t -Bu (25.6g, 266mmol), 930 ml of toluene was used to obtain 9.11 g of product (yield: 77%) using the Sub 4-2 synthesis method.

Although the synthesis method for some of the specific compounds of Sub 4 has been exemplified, compounds represented by formulas Sub 4 to Sub 1-81, which will be described later, can also be synthesized using the same synthesis method.

Synthesis of Final Product (1)

Synthesis example of P1-54

After dissolving Sub 1-32 (9.6g, 24mmol) in toluene in a round bottom flask, Sub 4-9 (6.4g, 20mmol), Pd ₂ (dba) ₃ (0.5g, 0.6mmol), and P(t- After adding Bu) ₃ (0.2g, 2mmol), NaO t -Bu (5.8g, 60mmol), and toluene (300 mL), the reaction proceeds at 100°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was recrystallized using a silicagel column to obtain 12.0 g of product (yield: 78%).

Synthesis example of P1-48

After dissolving Sub 1-1-6 (9.6g, 24mmol) in toluene, Sub 2-36 (7.0g, 20mmol), Pd ₂ (dba) ₃ (0.5g, 0.6mmol), P(t-Bu) After adding ₃ (0.2g, 2mmol), NaO t -Bu (5.8g, 60mmol), and toluene (300 mL), 12.5g of product (yield: 78%) was obtained using the P1-54 synthesis method above.

Synthesis example of P1-31

After dissolving Sub 1-27 (11.4g, 24mmol) in toluene, Sub 4-7 (5.9g, 20mmol), Pd ₂ (dba) ₃ (0.5g, 0.6mmol), P(t-Bu) ₃ ( After adding 0.2g, 2mmol), NaO t -Bu (5.8g, 60mmol), and toluene (300 mL), 13.7g of product (yield: 83%) was obtained using the P1-54 synthesis method above.

Synthesis example of P1-34

After dissolving Sub 1-52 (5g, 9.48mmol) in toluene (10ml), Sub 4-8 (6.55g, 18.97mmol), Pd ₂ (dba) ₃ (0.87g, 0.95mmol), P(t- After adding Bu) ₃ (0.31g, 1.52mmol), NaO t -Bu (5.47g, 56.9mmol), and toluene (100mL), product 12.02 (yield: 74%) was obtained using the above P1-54 synthesis method. got it

Synthesis example of P1-75

After dissolving Sub 1-47 (11.5g, 20.37mmol) in toluene (10ml), Sub 4-23 (8.34g, 20.37mmol), Pd ₂ (dba) ₃ (0.93g, 1.02mmol), P(t -Bu) ₃ (0.33g, 1.63mmol), NaO t -Bu (5.87g, 61.11mmol), and toluene (213mL) were added, respectively, and product 12.92 (yield: 71%) was obtained using the above P1-54 synthesis method. got it

Although the synthesis method for some of the specific compounds of the final product (1) is exemplified, compounds represented by the above-mentioned chemical formulas P1-1 to P1-77 can also be synthesized using the same synthesis method.

II. Synthesis of final product (2)

Compounds represented by Formula 3 according to the present invention (final product (2), for example, compounds represented by P2-1 to P1-72) can be prepared by reacting Sub 2 and Sub 4 as shown in the following reaction formula. It is not limited to this.

<Scheme 4>

Example of synthesis of Sub 2 (when L is not a single bond)

Sub 2 of Scheme 4 can be synthesized through the reaction route of Scheme 5 below, but is not limited thereto. Specific compounds of Sub 2 may be compounds represented by chemical formulas Sub 2-1 to Sub 2-39, which will be described later, but are not limited thereto.

<Scheme 5>

Synthesis example of Sub 2

(1) Sub 2-8 synthesis example

1) M 2-1 synthesis

After dissolving Sub 2-1 (75g, 274.55mmol) in 1372mL of DMF, Bispinacolborate (76.69g, 302.01mmol), PdCl ₂ (dppf) catalyst (6.03g, 8.24mmol), and KOAc (80.83g, 823.66mmol) were added in this order. After adding as directed and stirring for 24 hours to synthesize the borate compound, the obtained compound was separated through a silicagel column and recrystallization to obtain 72.10 g (82%) of the product.

2) Synthesis of Sub 2-8

After dissolving M 2-1 (30g, 93.68mmol) in 412mL of THF, 1-bromo-4-iodobenzene (26.50g, 93.68mmol), Pd(PPh ₃ ) ₄ (1.62g, 1.41mmol), NaOH (5.62g) , 140.52mmol), add 206mL of water, and stir to reflux. When the reaction was completed, extraction was performed with ether and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was recrystallized using a silicagel column to obtain 22.25 g (68%) of the product.

(2) Sub 2-10 synthesis example

Synthesis of Sub 2-10

After dissolving M 2-1 (30g, 93.68mmol) in 412mL of THF, 1-bromo-2-iodobenzene (26.50g, 93.68mmol), Pd(PPh ₃ ) ₄ (1.62g, 1.41mmol), NaOH (5.62g) , 140.52mmol), 206mL of water was used to obtain 19.96g (61%) of the product using the Sub 2-8 synthesis method.

(3) Sub 2-12 synthesis example

Synthesis of Sub 2-I-12

After dissolving naphthalen-1-ylboronic acid (85g, 494.22mmol) in 2175mL of THF, methyl 5-chloro-2-iodobenzoate (146.53g, 494.22mmol), Pd(PPh ₃ ) ₄ (8.57g, 7.41mmol), NaOH (29.65g, 741.32mmol), add 1087mL of water, and stir to reflux. When the reaction was completed, extraction was performed with ether and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was recrystallized using a silicagel column to obtain 90.93 g (62%) of the product.

Synthesis of Sub 2-II-12

Sub 2-I-12 (90.93g, 306.42mmol) was dissolved in Methanesulfonic acid (996ml) and stirred at 50-60 °C. When the reaction was completed, the temperature was lowered to 0 °C, water was added, and the precipitated solid was filtered. Washed with a small amount of water, re-dissolved in CH ₂ Cl ₂ , dried with MgSO ₄ and concentrated, the resulting compound was recrystallized on a silicagel column to obtain 37.31 g of product (yield: 46%).

Synthesis of Sub 2-III-12

Sub 2-II-12 (37.31g, 140.95mmol) obtained in the above synthesis was dissolved in Ethylene glycol (564mL), then Hydrazine monohydrate (211.67g, 4228.4mmol), KOH (19.77g, 352.37mmol) was added and stirred at 185 °C. When the reaction was completed, the temperature was lowered to 0 °C, water was added, and the precipitated solid was filtered and washed with a small amount of water. After re-dissolving in CH ₂ Cl ₂ , drying with MgSO ₄ and concentrating, the resulting compound was recrystallized using a silicagel column to obtain 33.22 g of product. (yield: 94%)

Synthesis of Sub 2-IV-12

Dissolve Sub 2-III-12 (33.22g, 132.49mmol), KOt-Bu (44.60g, 397.48mmol), and DMSO (861ml) obtained in the above synthesis in a round bottom flask, stir at 0°C for 5 minutes, and leave at room temperature. Raised to iodomethane (56.42g, 397.48mmol) was added. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 35.46 g of product. (yield: 96%)

Synthesis of Sub 2-V-12

After dissolving Sub 2-IV-12 (35.46g, 127.20mmol) in 801mL of DMF, Bispinacolborate (35.53g, 139.92mmol), PdCl ₂ (dppf) catalyst (2.79g, 3.82mmol), KOAc (37.45g, 381.59mmol) ) were sequentially added and stirred for 24 hours to synthesize the borate compound. The obtained compound was separated through a silicagel column and recrystallization to obtain 39.57g (84%) of the product.

Synthesis of Sub 2-12

After dissolving Sub 2-V-12 (39.57g, 106.86mmol) in 470mL of THF, 1-bromo-4-iodobenzene (30.23g, 106.86mmol), Pd(PPh ₃ ) ₄ (1.85g, 1.60mmol), NaOH (6.41g, 160.29mmol), 26.88g (63%) was obtained from 235mL of water using the Sub 2-8 synthesis method.

Synthesis example of Sub 2-20

Synthesis of Sub 2-I-20

After dissolving 2-bromo-1,1'-biphenyl (46.6g, 199.91mmol) and 9-chloro-11H-benzo[a]fluoren-11-one (52.9g, 199.91mmol) in THF (1400ml), the reactants The temperature was lowered to -78°C, n-BuLi (2.5 M in hexane) (14.09g, 219.9mmol) was slowly added, and the reaction was stirred at room temperature for 4 hours. When the reaction was completed, the reactant was quenched in H ₂ O, water in the reactant was removed, filtered under reduced pressure, the organic solvent was concentrated, and the resulting product was separated using column chromatography to obtain 74.6 g of product. (yield: 89%)

Synthesis of Sub 2-II-20

Add a small amount of HCl and Acetic acid (704ml) to Sub 2-I-20 (74.6g, 178 mmol) and stir at 80°C for 1 hour. When the reaction was completed, the organic solvent was concentrated after filtration under reduced pressure, and the resulting product was separated using column chromatography to obtain 64.89 g of the product. (yield: 91%)

Synthesis of Sub 2-III-20

After dissolving Sub 2-II-20 (64.89g, 161.86mmol) in 809mL of DMF, Bispinacolborate (45.21g, 178.04mmol), PdCl ₂ (dppf) catalyst (3.55g, 4.86mmol), KOAc (47.65g, 485.57mmol) ) were sequentially added and stirred for 24 hours to synthesize the borate compound. The obtained compound was separated through a silicagel column and recrystallization to obtain 65.36g (82%) of the product.

Synthesis of Sub 2-20

After dissolving Sub 2-III-20 (30g, 60.92mmol) in 268mL of THF, 4'-bromo-3-iodo-1,1'-biphenyl (21.87g, 60.92mmol), Pd(PPh ₃ ) ₄ (1.06 g, 0.91mmol), NaOH (3.66g, 91.38mmol), and 235mL of water were used to obtain 24.39g (67%) of the product using the synthesis method of Sub 2-8.

Synthesis example of Sub 2-25

Synthesis of Sub 2-I-25

After dissolving 2-bromo-1,1'-biphenyl (50g, 214.49mmol) and 2-chloro-9H-fluoren-9-one (46.04g, 214.49mmol) in THF (1501ml), the temperature of the reactants was -78 After lowering the temperature to ℃, n-BuLi (2.5 M in hexane) (15.11 g, 235.94 mmol) was used to obtain 68.83 g of product using the Sub 2-I-20 synthesis method. (yield: 87%)

Synthesis of Sub 2-II-25

Sub 2-I-25 (68.83g, 164.3mmol) was mixed with a small amount of HCl and Acetic acid (361ml) using the above Sub 2-II-20 synthesis method to obtain 58.27g of product. (yield: 89%)

Synthesis of Sub 2-III-25

After dissolving Sub 2-II-25 (58.27g, 166.08mmol) in 830mL of DMF, Bispinacolborate (46.39g, 182.69mmol), PdCl ₂ (dppf) catalyst (3.65g, 4.98mmol), KOAc (48.9g, 498.25mmol) ), 58.78g (80%) of the product was obtained using the above Sub 2-III-20 synthesis method.

Synthesis of Sub 2-25

After dissolving Sub 2-III-25 (58.78g, 132.88mmol) in 585mL of THF, 3,7-dibromodibenzo[b,d]thiophene (45.45g, 132.88mmol), Pd(PPh ₃ ) ₄ (2.30g, 1.99 mmol), NaOH (7.97g, 199.31mmol), and 292mL of water were used to obtain 29.09g (64%) of the product using the Sub 2-8 synthesis method above.

Synthesis example of Sub 2-31

Synthesis of Sub 2-I-31

2-bromo-1,1'-biphenyl (50g, 214.49mmol) and 7-chloro-11H-benzo[b]fluoren-11-one (56.78g, 214.49mmol) were mixed with THF (1501ml) and n-BuLi (2.5ml). M in hexane) (15.11g, 235.94mmol) was used to obtain 73.68g of product using the Sub 2-I-20 synthesis method. (yield: 82%)

Synthesis of Sub 2-II-31

Sub 2-I-31 (73.68g, 175.88mmol) was mixed with a small amount of HCl and Acetic acid (387ml) using the above Sub 2-II-20 synthesis method to obtain 60.64g of product. (Yield: 86%)

Synthesis of Sub 2-III-31

After dissolving Sub 2-II-31 (60.64g, 151.26mmol) in 953mL of DMF, Bispinacolborate (42.25g, 166.38mmol), PdCl ₂ (dppf) catalyst (3.32g, 4.54mmol), KOAc (44.53g, 453.77mmol) ), 61.82g (83%) of the product was obtained using the above Sub 2-III-20 synthesis method.

Synthesis of Sub 2-31

After dissolving Sub 2-III-31 (20g, 40.61mmol) in 179mL of THF, 1-bromo-3-iodobenzene (11.49g, 40.61mmol), Pd(PPh ₃ ) ₄ (0.70g, 0.61mmol), NaOH ( 2.44g, 60.92mmol) and 89mL of water were used to obtain 13.98g (66%) of the product using the synthesis method of Sub 2-8 above.

Although the synthesis methods for some of the specific compounds of Sub 2 have been exemplified above, compounds represented by chemical formulas Sub 2-1 to Sub 2-39, which will be described later, can also be synthesized using the same synthesis method.

Final Product ( 2) of synthesis

Synthesis example of P2-14

In a round bottom flask, Sub 2-1 (4g, 14.64mmol), Sub 4-67 (7.86g, 14.64mmol), Pd ₂ (dba) ₃ (0.67g, 0.73 mmol), P(t-Bu) ₃ (0.24) g, 1.17mmol), NaOt-Bu (4.22g, 43.93mmol), and toluene (154mL) were added and the reaction was carried out at 100°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was recrystallized using a silicagel column to obtain 7.58 g of product. (yield: 71%)

Synthesis example of P2-25

After dissolving Sub 2-9 (5.2g, 14.89mmol) in toluene, Sub 4-47 (5.98g, 14.89mmol), Pd ₂ (dba) ₃ (0.68g, 0.74mmol), P(t-Bu) ₃ (0.24g, 1.19mmol), NaO t -Bu (4.29g, 44.67mmol), and toluene (156mL) were used to obtain 7.28g of product (yield: 73%) using the above P2-14 synthesis method.

Synthesis example of P2-37

After dissolving Sub 2-6 (5.2g, 14.89mmol) in toluene, Sub 4-59 (6.86g, 14.89mmol), Pd ₂ (dba) ₃ (0.68g, 0.74mmol), P(t-Bu) ₃ (0.24g, 1.19mmol), NaO t -Bu (4.29g, 44.67mmol), and toluene (156mL) were used to obtain 7.38g of product (yield: 68%) using the above P2-14 synthesis method.

Synthesis example of P2-39

After dissolving Sub 2-19 (6.5g, 11.83mmol) in toluene, Sub 4-12 (4.39g, 11.83mmol), Pd ₂ (dba) ₃ (0.54g, 0.59mmol), P(t-Bu) ₃ (0.19g, 0.95mmol), NaO t -Bu (3.41g, 35.49mmol), and toluene (124mL) were used to obtain 7.15g of product (yield: 72%) using the above P2-14 synthesis method.

Synthesis example of P2-43

After dissolving Sub 2-5 (5.2g, 12.16mmol) in toluene, Sub 4-19 (4.76g, 13.16mmol), Pd ₂ (dba) ₃ (0.6g, 0.66mmol), P(t-Bu) ₃ (0.21g, 1.05mmol), NaO t -Bu (3.79g, 39.46mmol), and toluene (138mL) were used to obtain 7.11g of product (yield: 80%) using the above P2-14 synthesis method.

Synthesis example of P2-64

After dissolving Sub 2-31 (6g, 11.51mmol) in toluene, Sub 4-33 (4.69g, 11.51mmol), Pd ₂ (dba) ₃ (0.53g, 0.58mmol), P(t-Bu) ₃ ( 0.19g, 0.92mmol), NaO t -Bu (3.32g, 34.52mmol), and toluene (121mL) were used to obtain 7.22g of product (yield: 74%) using the P2-14 synthesis method.

Synthesis example of P2-65

After dissolving Sub 2-32 (6.5g, 12.47mmol) in toluene, Sub 4-9 (4.01g, 12.47mmol), Pd ₂ (dba) ₃ (0.57g, 0.62mmol), P(t-Bu) ₃ (0.2g, 0.997mmol), NaO t -Bu (3.59g, 37.4mmol), and toluene (131mL) were used to obtain 7.31g of product (yield: 77%) using the above P2-14 synthesis method.

Although the synthesis method for some of the specific compounds of the final product (2) is exemplified, compounds represented by the above-mentioned chemical formulas P2-1 to P2-72 can also be synthesized using the same synthesis method.

III. Final product ( 3) of synthesis

Compounds represented by formulas 5 to 7 according to the present invention (final product (3), for example, compounds represented by P3-1 to P3-80) are prepared by reacting Sub 3 and Sub 4 as shown in Scheme 6 below. However, it is not limited to this.

<Scheme 6>

Sub 3 synthesis example

Sub 3 of Scheme 6 can be synthesized through the reaction route of Scheme 7 below, but is not limited thereto. Specific compounds of Sub 3 may be compounds represented by formulas Sub 3-1 to Sub 3-37, which will be described later, but are not limited thereto.

<Scheme 7>

Synthesis example of Sub 3-1

(1) M 3-1 synthesis

After dissolving M 3-I-1 (15.76 g, 63.78 mmol) in DMF (320ml) in a round bottom flask, Bis(pinacolato)diboron (17.82 g, 70.16 mmol), Pd(dppf)Cl ₂ (1.56 g, 1.91 mmol), KOAc (18.78 g, 191.35 mmol) was added and stirred at 90°C. When the reaction was completed, DMF was removed through distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 15.38 g of product (yield: 82%).

(2) Sub 3-4 synthesis

After dissolving M 3-1 (15.38g, 52.28mmol) obtained in the above synthesis with THF (230ml) in a round bottom flask, 1-bromo-4-iodobenzene (14.79g, 52.28mmol), Pd(PPh ₃ ) ₄ ( 0.91g, 0.78mmol), NaOH (3.14g, 78.43mmol), and water (115ml) were added and stirred at 80°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 12.17 g of product (yield: 72%).

Synthesis example of Sub 3-9

After dissolving M 3-1 (9g, 30.60mmol) obtained in the above synthesis in THF (134ml), 4'-bromo-3-iodo-1,1'-biphenyl (10.98g, 30.60mmol), Pd(PPh ₃ ) ₄ (0.53g, 0.46mmol), NaOH (1.84g, 45.89mmol), and water (67ml) were used to obtain 8.67g of product (yield: 71%) using the Sub 3-4 synthesis method.

Synthesis example of Sub 3-12

(1) M 3-I-2 synthesis

The starting material, 10-(3-bromophenyl)phenanthren-9-ol (63.74 g, 182.5 mmol), was added to a round bottom flask along with Pd(OAc) ₂ (4.1 g, 18.3 mmol) and 3-nitropyridine (2.27 g, 18.3 mmol). and dissolved in C ₆ F ₆ (270ml) and DMI (180ml), then tert -butyl peroxybenzoate (70.9 g, 365 mmol) was added and stirred at 90°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting compound was recrystallized using a silicagel column to obtain 26.62 g of product (yield: 42%).

(2) M 3-2 synthesis

After dissolving M 3-I-2 (26.62 g, 76.7 mmol) obtained in the above synthesis with DMF (385ml) in a round bottom flask, Bis(pinacolato)diboron (21.42 g, 84.3 mmol), Pd(dppf)Cl ₂ (1.88 g, 2.3 mmol), KOAc (22.57 g, 230 mmol) was used to obtain 20.25 g of product (yield: 67%) using the synthesis method of M 3-1.

(3) Sub 3-12

After dissolving M 3-2 (10g, 25.36mmol) obtained in the above synthesis in THF (111ml), 2-bromo-3'-iodo-1,1'-biphenyl (9.11g, 25.36mmol), Pd(PPh ₃ ) ₄ (0.44g, 0.38mmol), NaOH (1.52g, 38.04mmol), and water (56ml) were used to obtain 8.61g of product (yield: 68%) using the Sub 3-4 synthesis method.

Synthesis example of Sub 3-14

(1) M 3-3 synthesis

M 3-I-3 (32.76 g, 132.58 mmol), Bis(pinacolato)diboron (37.04 g, 145.84 mmol), Pd(dppf)Cl ₂ (3.25 g, 3.98 mmol), KOAc (39.04 g, 397.75 mmol) and DMF (660ml) were used to obtain 33.54 g of product (yield: 86%) using the M 3-1 synthesis method.

(2) Sub 3-14 synthesis

1-bromo-4-iodobenzene (11.54g, 40.79mmol), Pd(PPh ₃ ) ₄ (0.71g, 0.61mmol), NaOH (2.45g, 61.19mmol) were added to M 3-3 (12g, 40.79mmol) obtained from the above synthesis. mmol), THF (170ml), and water (90ml) were used to obtain 9.62g of product (yield: 73%) using the Sub 3-4 synthesis method.

Synthesis example of Sub 3-16

M 3-3 (11g, 37.93mmol) obtained from the above synthesis, 4-bromo-4'-iodo-1,1'-biphenyl (13.42g, 37.39mmol), Pd(PPh ₃ ) ₄ (0.65g, 0.56mmol) ), NaOH (2.24g, 56.09mmol), THF (165ml), and water (82ml) were used to obtain 11.20g of product (yield: 75%) using the Sub 3-4 synthesis method.

Synthesis example of Sub 3-19

1,3,5-tribromobenzene (10.70g, 34mmol), Pd(PPh ₃ ) ₄ (0.39g, 0.34mmol), NaOH (1.36g, 34mmol), M 3-3 (10g, 34mmol) obtained in the above synthesis, THF (150ml) and water (75ml) were used to obtain 9.29g of product (yield: 68%) using the Sub 3-4 synthesis method.

,Synthesis example of Sub 3-21

(1) M 3-4 synthesis

M 3-I-4 (25g, 100.37mmol), Bis(pinacolato)diboron (28.04g, 110.40mmol), Pd(dppf)Cl ₂ (2.2g, 3.01mmol), KOAc (29.55g, 301.10mmol) and DMF (632ml) were used to obtain 24.5g of product (yield: 83%) using the M 3-1 synthesis method.

(2) Sub 3-21 synthesis

M 3-4 (10g, 34mmol) obtained from the above synthesis, 2,7-dibromo-9,9-dimethyl-9H-fluorene (11.97g, 34mmol), Pd(PPh ₃ ) ₄ (0.59g, 0.51mmol), NaOH (2.04g, 51mmol), THF (150ml), and water (75ml) were used to obtain 10.16g of product (yield: 68%) using the Sub 3-4 synthesis method.

,Synthesis example of Sub 3-21

(1) M 3-I-5 synthesis

3-(4-bromophenyl)naphthalen-2-ol (55g, 183.84mmol), Pd(OAc) ₂ (4.13g, 18.38mmol), 3-nitropyridine (2.28g, 18.38mmol), C ₆ F ₆ (276ml) After dissolving in DMI (184ml), tert -butyl peroxybenzoate (71.42g, 367.68mmol) was used to obtain 51.85g of product (yield: 71%) using the above M 3-I-2 synthesis method.

(2) M 3-5 synthesis

After dissolving M 3-I-5 (30g, 100.96mmol) obtained in the above synthesis in DMF (636ml), Bis(pinacolato)diboron (28.1g, 111.06mmol), Pd(dppf)Cl ₂ (2.22g, 3.03mmol), KOAc (29.72g, 302.88mmol was used to obtain 26.41g of product (yield: 76%) using the above synthesis method of M 3-2.

(2) Sub 3-31 synthesis

1-bromo-3-iodobenzene (10.68g, 37.77mmol), Pd(PPh ₃ ) ₄ (0.65g, 0.57mmol), NaOH (2.27g, 56.65mmol) were added to M 3-4 (13g, 37.77mmol) obtained in the above synthesis. mmol), THF (166ml), and water (83ml) were used to obtain 9.59g of product (yield: 68%) using the Sub 3-4 synthesis method.

Above, the synthesis method for some of the specific compounds of Sub 3 has been exemplified, but compounds represented by the formulas Sub 3-1 to Sub 3-37, which will be described later, can also be synthesized using the same synthesis method.

Final Product (3) Synthesis example

Synthesis of P3-1

In a round bottom flask, Sub 3-1 (4g, 16.19mmol), Sub 4-9 (5.20g, 16.19mmol), Pd ₂ (dba) ₃ (0.74g, 0.81 mmol), P(t-Bu) ₃ (0.26) g, 1.30mmol), NaOt-Bu (4.67g, 48.57mmol), and toluene (170mL) were added and the reaction was carried out at 100°C. When the reaction was completed, extraction was performed with CH ₂ Cl ₂ and water, the organic layer was dried with MgSO ₄ and concentrated, and the resulting organic material was recrystallized using a silicagel column to obtain 7.03 g of product. (yield: 89%)

Synthesis of P3-20

After dissolving Sub 3-18 (4.60g, 11.52mmol) in toluene, Sub 4-49 (5.08g, 11.52mmol), Pd ₂ (dba) ₃ (0.53g, 0.58mmol), P(t-Bu) ₃ (0.19g, 0.92mmol), NaO t -Bu (3.32g, 34.56mmol), and toluene (121mL) were used to obtain 7.08g of product (yield: 81%) using the P3-1 synthesis method.

Synthesis of P3-25

After dissolving Sub 3-22 (3.5g, 11.78mmol) in toluene, Sub 4-76 (6.65g, 11.78mmol), Pd ₂ (dba) ₃ (0.54g, 0.59mmol), P(t-Bu) ₃ (0.19g, 0.94mmol), NaO t -Bu (3.4g, 35.34mmol), and toluene (124mL) were used to obtain 7.17g of product (yield: 78%) using the P3-1 synthesis method.

Synthesis of P3-46

After dissolving Sub 3-6 (5.5g, 13.68mmol) in toluene, Sub 4-8 (3.36g, 13.68mmol), Pd ₂ (dba) ₃ (1.25g, 1.37mmol), P(t-Bu) ₃ (0.44g, 2.19mmol), NaO t -Bu (7.89g, 82.07mmol), and toluene (144mL) were used to obtain 7.4g of product (yield: 74%) using the P3-1 synthesis method.

Synthesis of P3-51

After dissolving Sub 3-9 (5.5g, 13.77mmol) in toluene, Sub 4-9 (4.43g, 13.77mmol), Pd ₂ (dba) ₃ (0.63g, 0.69mmol), P(t-Bu) ₃ (0.22g, 1.1mmol), NaO t -Bu (3.97g, 41.32mmol), and toluene (145mL) were used to obtain 7.31g of product (yield: 83%) using the P3-1 synthesis method.

Synthesis of P3-64

After dissolving Sub 3-13 (5g, 15.47mmol) in toluene, Sub 4-20 (5.59g, 15.47mmol), Pd ₂ (dba) ₃ (0.71g, 0.77mmol), P(t-Bu) ₃ ( 0.25g, 1.24mmol), NaO t -Bu (4.46g, 46.4mmol), and toluene (162mL) were used to obtain 7.19g of product (yield: 77%) using the P3-1 synthesis method.

Synthesis of P3-72

After dissolving Sub 3-29 (5.5g, 14.74mmol) in toluene, Sub 4-33 (6g, 14.74mmol), Pd ₂ (dba) ₃ (0.67g, 0.74mmol), P(t-Bu) ₃ ( 0.24g, 1.18mmol), NaO t -Bu (4.25g, 44.2mmol), and toluene (155mL) were used to obtain 7.53g of product (yield: 73%) using the P3-1 synthesis method.

Above, the synthesis method for some of the specific compounds of Final product (3) has been exemplified, but compounds represented by the above-mentioned chemical formulas P3-1 to P3-80 can also be synthesized using the same synthesis method.

Hereinafter, specific compounds of Sub 1, Sub 2, and Sub 3 are shown as examples, but are not limited thereto.

Example of Sub 1

Example of Sub 3-1

Example of Sub 4-1

Meanwhile, exemplary synthesis examples of the present invention represented by Formulas 1 to 6 have been described above, but these are all Buchwald-Hartwig cross coupling reaction, Suzuki cross-coupling reaction, and PPh ₃ -mediated reductive cyclization reaction ( J. Org . Chem . . 2005, 70 , 5014.), Intramolecular acid-induced cyclization reaction ( J. mater. Chem . 1999, 9 , 2095.), Pd(II)-catalyzed oxidative cyclization reaction ( Org . Lett . 2011, 13 , 5504) , Grignard reaction, Cyclic Dehydration reaction, etc., and those skilled in the art will easily understand that the reaction proceeds even if other substituents defined in Formulas 1 to 6 are combined in addition to the substituents specified in the specific synthesis examples.

Meanwhile, some of the hole transport layer 135, the first light emitting auxiliary layer 140R', and the second light emitting auxiliary layer 140G' may be made of the same compound or different compounds.

Here, the third auxiliary light emitting layer 140B' is disposed on the first auxiliary light emitting layer 140R' and the second auxiliary light emitting layer 140G', and the first to third subpixels SP1, SP2, By being commonly disposed in SP3), the charge balance within the organic light-emitting layer 145 can be matched to increase efficiency and increase lifespan. In particular, the luminous efficiency in the third subpil cell (SP3) can be relatively high and lifespan can be relatively long. there is. In addition, the organic light emitting device 200 according to one embodiment has a reduction in excess polarons that cause dopant quenching and device deterioration in the organic light emitting layer 145, thereby reducing the amount of excess polaron generated due to the excess polarons. Dopant quenching and device degradation can be reduced, thereby increasing lifespan.

Meanwhile, the organic light emitting device 200 may additionally include a hole injection layer 130 between the first electrode 120 and the hole transport layer 135. However, the organic light emitting device 200 according to one embodiment performs the functions of the hole transport layer 135 and the hole injection layer 130 at the same time, thereby eliminating the configuration of the hole injection layer 130.

Additionally, the organic light emitting device 200 may sequentially include an electron transport layer 160 and an electron injection layer 170 on the organic light emitting layer 145. Additionally, a second electrode 180 may be disposed on the electron injection layer 170.

Specifically, the electron transport layer 160 may be disposed on the organic light-emitting layer 145. In addition, the electron transport layer 160 is a layer that functions to transport electrons injected from the second electrode 180 to the light-emitting layer, for example, Alq3, BCP (2,9-Dimethyl-4,7-diphenyl-1 ,10-phenanthroline, ,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen(4,7-Diphenyl-1,10-phenanthroline, 4,7-diphenyl-1,10 -Phenanthroline), TAZ(3-(4-Biphenylyl)-4-phenyl-5tert-butylphenyl-1,2,4-triazole, 3-(4-biphenylyl)-4-phenyl-5-tert- Butylphenyl-1,2,4-triazole), NTAZ(4(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole, 4-(naphthalen-1-yl)- 3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD(2-(4-Biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole, 2 -(4-biphenylyl)-5-(4-tert-butylphenyl)1,3,4-oxadiazole), BAlq(Bis(2-methyl-8-quinolinolato-N1,O8)-(1, 1'-Biphenyl-4-olato)aluminum, bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum), Bebq2(beryllium bis (benzoquinolin-10-olate, beryllium bis(benzoquinolin-10-noate)), ADN(9,10-di(naphthalene-2-yl)anthrascene, 9,10-di(naphthalene-2yl)anthracene) Materials such as the like can be used, but are not limited to this.

Such an electron transport layer 160 may be formed using a vacuum deposition method, spin coating method, casting method, etc. When forming the electron transport layer 160 through vacuum deposition and spin coating, the conditions vary depending on the compound used, but can generally be selected from a range of conditions that are almost the same as those for forming the hole injection layer 130.

Additionally, the thickness of the electron transport layer 160 may be about 100Å to about 1,000Å, for example, about 150Å to about 500Å. When the thickness of the electron transport layer 160 satisfies the range described above, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage.

Meanwhile, the electron transport layer 160 may include an electron transport organic compound and a metal-containing material. The metal-containing material may include Li complex. Non-limiting examples of Li complexes include lithium quinolate (LiQ), etc.

Additionally, an electron injection layer 170 having a function of facilitating injection of electrons from the second electrode 180 may be disposed on the electron transport layer 160. The electron injection layer 170 may use electron injection layer materials such as LiF, NaCl, CsF, Li 2O, BaO, etc., but is not limited thereto. The deposition conditions for the electron injection layer 170 vary depending on the compound used, but can generally be selected from a range of conditions that are substantially the same as those for forming the hole injection layer 130.

The thickness of the electron injection layer 170 may be about 1Å to about 100Å, or about 3Å to about 90Å. When the thickness of the electron injection layer 170 satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage. In addition, the electron transport layer 160 and the electron injection layer 170 of the organic light emitting device 200 according to one embodiment are not limited thereto, and the electron transport layer 160 and the electron injection layer 170 have an electron transport function and It can be replaced with a functional layer that simultaneously has an electron injection function.

Meanwhile, a capping layer (not shown) may be formed on the second electrode 180 to improve optical properties and maximize luminous efficiency. The capping layer (not shown) may be made of, for example, a metal oxide layer, a metal nitride layer, or a metal nitride layer. The capping layer (not shown) is, for example, MoOx (x=2~4), Al2O3, Sb2O3, BaO, CdO, CaO, Ce2O3, CoO, Cu2O, DyO, GdO, HfO2, La2O3, Li2O, MgO, NbO, NiO, Nd2O3, PdO, Sm2O3, ScO, SiO2, SrO, Ta2O3, TiO, WO3, VO2, YbO, Y2O3, ZnO, ZrO, AlN, BN, NbN, SiN, TaN, TiN, VN, YbN, ZrN, SiON, It may be made of AlON or a mixture thereof.

At this time, the organic light emitting device 200 has the remaining layers between the first electrode 120 and the second electrode 180 except for the hole transport layer 135, the light emitting auxiliary layer 140, and the organic light emitting layer 145 removed. may include a configured configuration. In addition, the organic light emitting device 200 may further include a hole blocking layer, an electron blocking layer, a buffer layer, etc. in addition to the above-mentioned components, and the hole transport layer 135 may serve as an electron blocking layer or the electron transport layer 160 ) etc. may serve as a hole blocking layer.

In addition, although not shown in FIG. 1, the organic light-emitting device 200 according to one embodiment includes a protective layer formed on at least one side of the first electrode 120 and the second electrode 180, which is opposite to the organic light-emitting layer 145. It may further include a capping layer or a light efficiency improvement layer. A micro cavity effect can be achieved through improved light efficiency formed on one side opposite to the organic light emitting layer 145.

Specifically, in the organic light emitting device 200 according to one embodiment, the light emitted from the first to third organic light emitting layers 145R, 145G, and 145B is between the first electrode 120 and the second electrode 180. It may cause interference as it travels back and forth. At this time, when the distance between the first electrode 120 and the second electrode 180 corresponds to a distance that can cause resonance, light with an integer multiple wavelength causes constructive interference, which increases in intensity and causes light of a different wavelength Causes destructive interference and weakens the intensity. This process of back and forth and interference of light is called a micro cavity.

Here, the distance between the first electrode 120 and the second electrode 180 corresponds to an integer multiple of the wavelength of light emitted from the first to third organic emission layers 145R, 145G, and 145B for each subpixel. Hereinafter, with reference to FIG. 2, it will be explained that the optical path length of the light emitted from the organic light emitting layer 145 is varied for each subpixel using the thickness of the light emitting auxiliary layer 140.

Figure 2 is a diagram showing the thickness of light-emitting auxiliary layers of an organic light-emitting device according to an embodiment. Referring to FIG. 2, a light emitting auxiliary layer 140 is disposed between the organic light emitting layer 145 and the hole transport layer 135.

Specifically, a first light-emitting auxiliary layer (140R') and a third light-emitting auxiliary layer (140B') are disposed between the first organic light-emitting layer (145R) and the hole transport layer 135. In addition, a second light-emitting auxiliary layer (140G') and a third light-emitting auxiliary layer (140B') are disposed between the second organic light-emitting layer (145G) and the hole transport layer 135. Additionally, only the third auxiliary light emitting layer 140B' is disposed between the third organic light emitting layer 145B and the hole transport layer 135.

The light-emitting auxiliary layer 140 may be a layer for adjusting the resonance distance for each color of the organic light-emitting layer 145. The first auxiliary light emitting layer 140R', the second auxiliary light emitting layer 140G', and the third auxiliary light emitting layer 140B' emit red light in the first to third subpixels SP1, SP2, and SP3. In order to control the resonance distance of green light emission and the area where electrons and holes recombine, each can be formed to have an appropriate thickness. At this time, the first light-emitting auxiliary layer (140R'), the second light-emitting auxiliary layer (140G'), and the third light-emitting auxiliary layer (140B') may be added to match the resonance distance for each color.

Meanwhile, the sum of the thickness T1 of the first light-emitting auxiliary layer 140R' and the thickness T3 of the third light-emitting auxiliary layer 140B' disposed between the first organic light-emitting layer 145R and the hole transport layer 135. When only the first light-emitting auxiliary layer (140R') is disposed between the third organic light-emitting layer (145R) and the hole transport layer 135, the thickness (T1) of only the first light-emitting auxiliary layer (140R') is the same or substantially the same. You can.

In addition, the thickness (T2) of the second light-emitting auxiliary layer (140G') and the thickness (T3) of the third light-emitting auxiliary layer (140B') disposed between the second organic light-emitting layer (145G) and the hole transport layer 135. The sum is the same or substantially the same as the thickness (T2) of only the second light-emitting auxiliary layer (140G') when only the second light-emitting auxiliary layer (140G') is disposed between the second organic light-emitting layer (145G) and the hole transport layer 140. can do.

In addition, because the third auxiliary light emitting layer 140B' is commonly disposed in the first subpixel SP1, the second subpixel SP2, and the third subpixel SP3, the wavelength of the emitted light is the largest. The thickness T1 of the large first light-emitting auxiliary layer 140R' may be thicker than the thickness T2 of the second light-emitting auxiliary layer 140G', which has a relatively small wavelength. At this time, the first light emitting auxiliary layer 140R’ may have a thickness of about 30 Å to about 700 Å, for example, about 50 Å to about 200 Å. Additionally, the second light emitting auxiliary layer 140G' may have a thickness of about 30 Å to about 300 Å, for example, about 50 Å to about 100 Å.

The second light emitting auxiliary layer (140G') may be thicker than the third light emitting auxiliary layer (140B'). Here, the third light emitting auxiliary layer 140B' may be 30Å to about 250Å, for example, about 50Å to about 100Å.

In addition, in the organic light emitting device 200 according to one embodiment, the optical path length of the light emitted from the organic light emitting layer 145 is varied for each subpixel using the thickness of the light emitting auxiliary layer 140 to form a micro cavity. (microcavity) effect can be implemented.

As described above, the second subpixel (eg, green subpixel) of the organic light emitting device 200 according to the embodiment has excellent luminance-current efficiency characteristics. In detail, by having a different structure of the organic light emitting device 200 in one embodiment as shown in FIG. 1, not only does it satisfy the micro cavity effect, but also in terms of energy level, it can transmit energy from the first electrode 120 through the hole transport layer 135. This is because holes can be efficiently transported step by step according to the HOMO level in the order of the third light-emitting auxiliary layer (150B') and the second light-emitting auxiliary layer (150R').

Next, referring to FIG. 3, the HOMO levels of the components of the organic light-emitting device according to an embodiment are as follows. Figure 3 is a diagram showing HOMO levels of a hole transport layer and a light-emitting auxiliary layer in an organic light-emitting device according to an embodiment.

Referring to FIG. 3, the light emitting auxiliary layer 140 may serve to assist hole transport for each color of the hole transport layer 135. In addition, the first light-emitting auxiliary layer (140R'), the second light-emitting auxiliary layer (140G'), and the third light-emitting auxiliary layer (140B') each have an appropriate energy level, for example, HOMO, to assist hole transport for each color. It can be formed to have a (Highest Occupied Molecular Orbital) level.

Specifically, the HOMO level (H2) of the first light-emitting auxiliary layer (140R') disposed between the hole transport layer 135 and the first organic light-emitting layer (145R) is the HOMO level (H1) of the hole transport layer 135. It can be bigger than In addition, the HOMO level (H3) of the second light-emitting auxiliary layer (140G') disposed between the hole transport layer 135 and the second organic light-emitting layer (145G) is greater than the HOMO level (H1) of the hole transport layer 135. You can. In addition, the HOMO level (H3) of the second light-emitting auxiliary layer (140B') disposed between the hole transport layer 135 and the third organic light-emitting layer (145B) is greater than the HOMO level (H1) of the hole transport layer 135. You can.

That is, the HOMO level (H2, H3, H4) of the light emitting auxiliary layer 150 may be greater than the HOMO level (H1) of the hole transport layer 135.

In addition, the HOMO level (H3) of the second light-emitting auxiliary layer (140G') disposed in the area between the hole transport layer 135 and the third light-emitting auxiliary layer (140B') is the HOMO level of the third light-emitting auxiliary layer (140B'). It can be made larger than (H4). In other words, the HOMO level (H3) of the second light-emitting auxiliary layer (140G') may be greater than the HOMO level (H4) of the third light-emitting auxiliary layer (140B').

In addition, the HOMO level (H2) of the first light-emitting auxiliary layer (140R') disposed in the area between the hole transport layer 135 and the third light-emitting auxiliary layer (140B') is that of the third light-emitting auxiliary layer (140B'). It can be made larger than the HOMO level (H4). In other words, the HOMO level (H2) of the first light-emitting auxiliary layer (140R') may be greater than the HOMO level (H4) of the third light-emitting auxiliary layer (140B').

That is, the HOMO level (H4) of the third auxiliary light emitting layer (140B') is greater than the HOMO level (H1) of the hole transport layer 135 and the HOMO level (H3) of the second auxiliary light emitting layer (140G') or It may be smaller than the HOMO level (H4) of the third light-emitting auxiliary layer (140R').

Meanwhile, the material of the first light-emitting auxiliary layer (140R'), the second light-emitting auxiliary layer (140G'), and the third light-emitting auxiliary layer (140B') may be the above-mentioned hole transport material that satisfies the energy level. At this time, from the first electrode of the organic light emitting device through the hole transport layer 135, the third light emitting auxiliary layer 140B', the second light emitting auxiliary layer 140G', and the first light emitting auxiliary layer 140R' are sequentially formed. Holes can be transported.

Specifically, the difference in HOMO levels (△HOMO=H2-H1) between the hole transport layer 135 and the first light-emitting auxiliary layer (140R') and the difference between the hole transport layer 135 and the second light-emitting auxiliary layer (140G') The difference in HOMO levels (△HOMO=H3-H1) is relatively larger than the difference in HOMO levels (△HOMO=H4-H1) between the hole transport layer 135 and the third light-emitting auxiliary layer (140B'), so the organic Holes are first transported from the first electrode of the light emitting device to the first light emitting auxiliary layer 140R' or the second light emitting auxiliary layer 140G' through the hole transport layer 135 through the third light emitting auxiliary layer 140B'. ) may be less efficient than transporting holes first.

Conversely, since the HOMO level is in the order of the hole transport layer 135, the third light-emitting auxiliary layer (140B'), the second light-emitting auxiliary layer (140G'), and the first light-emitting auxiliary layer (140R'), the first light-emitting auxiliary layer (140R') of the organic light-emitting device Holes are efficiently emitted step by step from the electrode through the hole transport layer 135 to the third auxiliary light emitting layer (140B'), the second auxiliary light emitting layer (140G'), and the first auxiliary light emitting layer (140R') according to the HOMO level. can be transported to

The organic light emitting device according to the above-described embodiment is compared with the organic light emitting device according to the comparative example as follows. Figure 4 is a cross-sectional view of an organic light-emitting device according to a comparative example.

Referring to FIG. 4, the organic light emitting device 300 according to the comparative example has a first light emitting auxiliary layer (240R'), a second light emitting auxiliary layer (240G'), and a third light emitting auxiliary layer (240B') for each subpixel. It may be the same as the organic light-emitting device according to the embodiment described with reference to FIG. 1, except that the first organic light-emitting layer 245R, the second organic light-emitting layer 245G, and the third organic light-emitting layer 24BR are disposed thereon. there is.

In this way, in terms of hole transport ability or hole mobility according to the HOMO level, as shown in FIG. 3, the first light emitting auxiliary layer 140R', the second light emitting auxiliary layer 140G', and the first light emitting auxiliary layer 140G' 3 When compared to the structure in which the first organic emission layer 145R, the second organic emission layer 145G, and the third organic emission layer 145B are disposed on the emission auxiliary layer 140B', the organic emission according to the above-described embodiment The device 200 transports holes from the hole transport layer 135 to the second organic light-emitting layer 145G through the second light-emitting auxiliary layer 140G' and the third light-emitting auxiliary layer 140B', or through the first light-emitting auxiliary layer ( Since holes are transported to the first organic light emitting layer 145R through the third light emitting auxiliary layer 140R') and the third light emitting auxiliary layer 140B', the hole movement ability can be improved.

Meanwhile, the organic light emitting device 200 according to one embodiment may be manufactured using vacuum deposition. Some of the organic layers including the hole transport layer 135, the light-emitting auxiliary layer 140, and the organic light-emitting layer 145 use various polymer materials and are processed through a solution process or solvent process rather than a vacuum deposition method, such as a spin coating process, It can be manufactured with fewer layers by methods such as a nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blading process, screen printing process, or thermal transfer method.

Since the organic material layer including the hole transport layer 135, the auxiliary light emitting layer 140, and the organic light emitting layer 145 can be formed by various methods, the scope of the present invention is not limited by the forming method.

Hereinafter, a method of manufacturing an organic light-emitting device according to another embodiment using a vacuum deposition method will be described. In a method of manufacturing an organic light emitting device according to another embodiment by a vacuum deposition method, the material or thickness of each layer may be the same as described with reference to FIGS. 1 to 3.

The organic light emitting device according to the above-described embodiment can be manufactured using a total of five masks. This configuration will be described with reference to FIGS. 5A to 5G as follows. Figures 5a to 5g are diagrams showing a method of manufacturing an organic light emitting device according to an embodiment of the present invention.

Referring to FIGS. 5A to 5G , the organic light emitting device according to one embodiment uses only a total of five masks (first to fifth masks) to form a light emitting auxiliary layer 140 and an organic light emitting layer 145 for each subpixel. can do. In detail, a total of two masks are used to form the light-emitting auxiliary layer 140 on the substrate 100 divided into first to third subpixels (SP1, SP2, and SP3), and the light-emitting auxiliary layer 140 Since a total of three masks are used to form the organic light emitting layer 145 disposed on the organic light emitting layer 145, the organic light emitting device according to one embodiment can be formed using a total of five masks.

In particular, the third light-emitting auxiliary layer 140B' among the light-emitting auxiliary layers 140 is shared by the first to third subpixels SP1, SP2, and SP3, thereby patterning the third light-emitting auxiliary layer 140B'. Since the process can be omitted, only five masks can be used in the manufacturing process of the organic light emitting device according to one embodiment.

Meanwhile, the organic light emitting device 300 according to the comparative example shown in FIG. 4 has a first light emitting auxiliary layer (240R'), a second light emitting auxiliary layer (240G'), and a third light emitting auxiliary layer (240B') for each pixel. It has a structure in which the first organic light-emitting layer 245R, the second organic light-emitting layer 245G, and the third organic light-emitting layer 245B are disposed thereon, and when manufacturing such a structure, a total of six masks must be used. However, when manufacturing the organic light emitting device 200 according to the embodiment described with reference to FIGS. 5A to 5G, only a total of five masks (first to fifth masks) are used, thereby improving process efficiency and reducing organic light emission. It is possible to increase the area of the organic light emitting display device including the device 200.

Next, with reference to FIG. 6, an organic light emitting device according to another embodiment will be examined as follows. Figure 6 is a cross-sectional view of an organic light emitting device according to another embodiment.

Referring to FIG. 6, an organic light emitting device according to another embodiment includes two or more subpixels (a, b) on a substrate. And, each subpixel (a, b) is connected to a first electrode, a second electrode disposed on the first electrode to face the first electrode, and two or more subpixels between the first electrode and the second electrode. Two or more organic light emitting layers 345 of different colors disposed, a hole transport layer 335 disposed between the first electrode and the organic light emitting layer 345, and disposed between the hole transport layer 335 and the organic light emitting layer 345. It may include a light emitting auxiliary layer 340.

At this time, the light-emitting auxiliary layer 450 includes an individual light-emitting auxiliary layer 340a' disposed in at least one subpixel (a, b) among two or more subpixels (a, b), and the individual light-emitting auxiliary layer. It is disposed on 340a' and may include a common auxiliary light emitting layer 340b' commonly disposed in the two or more subpixels (a, b).

Figure 6 shows a configuration in which one pixel (P) consists of two subpixels (a, b), but the organic light emitting device according to another embodiment is not limited to this, and one pixel (P) is composed of two subpixels (a, b). Subpixels may consist of 2 to 4 pieces.

Here, when there are three subpixels constituting one pixel (P), the corresponding organic light emitting device is the same as the organic light emitting device 200 described with reference to FIG. 1 . In addition, when one pixel (P) is composed of four subpixels, an organic light emitting device in which one subpixel (for example, a white subpixel) is added to the organic light emitting device 200 described with reference to FIG. 1. corresponds to

Additionally, the organic light emitting layer may include 2 to 4 organic light emitting layers disposed in each of 2 to 4 subpixels. Here, when one pixel (P) consists of two subpixels, as shown in FIG. 4, the organic emission layer 345 may include a first organic emission layer 345a and a second organic emission layer 345b. .

In addition, the light emitting auxiliary layer 340 may include a common light emitting auxiliary layer commonly disposed in 2 to 4 subpixels and 1 to 3 individual light emitting auxiliary layers disposed in each of 1 to 3 subpixels. there is.

Next, an organic light emitting display device to which embodiments of the present invention can be applied will be examined with reference to FIG. 7 as follows. Figure 7 is a conceptual diagram of an organic light emitting display device to which embodiments can be applied.

Referring to FIG. 7, an organic light emitting display device 500 to which embodiments of the present invention can be applied has n gate lines (GL1, ..., GLn, n: a natural number) oriented in a first direction (e.g., horizontal direction). ), a display panel 510 in which m data lines (DL1, ..., DLm, m: natural numbers) are formed in a second direction (e.g., vertical direction) intersecting the first direction, and m data A data driver 520 that drives the lines (DL1, ..., DLm), a gate driver 530 that sequentially drives n gate lines (GL1, ..., GLn), and a data driver 520. and a timing controller 540 that controls the gate driver 530.

In the display panel 510, subpixels (SP: Subpixels) are formed in a matrix form at each point where one data line and one or more gate lines intersect. Due to these multiple subpixels, multiple pixels are arranged on the display panel 510 in a matrix form.

In addition, the timing controller 540 starts scanning according to the timing implemented in each frame, and converts the image data input from the interface to fit the data signal format used by the data driver 520 to produce converted image data (Data). Outputs and controls data operation at an appropriate time according to the scan.

This timing controller 540 sends various control signals such as a data control signal (DCS: Data Control Signal) and a gate control signal (GCS: Gate Control Signal) to control the data driver 520 and the gate driver 530. Can be printed.

And, the gate driver 530 sequentially supplies scan signals of the on voltage or off voltage to the n gate lines (GL1, ..., GLn) according to the control of the timing controller 540. Then, n gate lines (GL1, ..., GLn) are sequentially driven.

The data driver 520 stores the input image data in a memory (not shown) under the control of the timing controller 540, and when a specific gate line is opened, the corresponding image data is converted into analog format. It is converted into a data voltage (Vdata) and supplied to m data lines (DL1, ..., DLm), thereby driving m data lines (DL1, ..., DLm).

Meanwhile, the organic light emitting display device 500 shown in FIG. 7 includes an organic light emitting display panel 510 including the organic light emitting elements 200 and 300 of the present invention described above and a device for controlling the organic light emitting display panel 510. It may include an electronic device including a control unit. At this time, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game consoles, various TVs, and various computers.

Next, the pixel structure of the organic light emitting display panel described above is as follows. FIG. 8 is a diagram showing the pixel structure of the organic light emitting display panel of FIG. 7. Referring to Figures 7 and 8, on the display panel 510, pixels (Pij, i=1, 2, ..., j=1, 2,...) in row i and column j are arranged in a matrix form.

Each pixel (Pij) may include 3 subpixels. That is, each pixel Pij may include a red subpixel (R), a green subpixel (G), and a blue subpixel (B). Here, the shape and arrangement of each pixel (Pij) and the number of subpixels may be modified in various ways, and other pixels, such as white subpixels that display white, may be further included.

Meanwhile, each pixel (Pij) of the organic light emitting display panel 510 has a source, drain, gate, and active layer in the first subpixel (R), second subpixel (G), and third subpixel (B), respectively. Includes a driving transistor.

Additionally, each pixel (Pij) emits different colors on the substrate and includes the organic light emitting device 200 shown in FIG. 1. At this time, the first electrode of each organic light emitting device disposed in the first subpixel (R), second subpixel (G), and third subpixel (B) is electrically connected to one of the source and drain of the driving transistor. It can be connected to .

Additionally, each pixel (Pij) may include a switching transistor that switches the data voltage to the driving transistor and a storage capacitor (Cst) that maintains this data voltage for a certain period of time, for example, one frame. there is.

The switching transistor and driving transistor are n-channel field effect transistors (FETs), but at least one of them may be a p-channel field effect transistor. Here, the connection relationship between the driving transistor, switching transistor, storage capacitor (Cst), and organic light emitting device is only an example, and is not limited to the connection relationship described above.

Meanwhile, the organic light emitting display device and the organic light emitting device thereof in the above-described embodiments of the present invention have the effect of minimizing the patterning process of the light emitting areas during manufacturing.

Manufacturing evaluation of organic electric devices

[Example]

First, a 4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine (abbreviated as 2-TNATA) film was vacuum deposited on the ITO layer (anode) formed on the glass substrate to create 100 nm thick holes. After forming the injection layer, the hole transport compound of the formulas 1 to 4 (for example, P2-41) was vacuum deposited to a thickness of 1200 nm on the hole injection layer to form a hole transport layer.

Afterwards, a first light-emitting auxiliary layer (red light-emitting auxiliary layer) disposed in the first subpixel that satisfies the thickness conditions of FIGS. 2 and 3 with a compound of Chemical Formulas 1 to 4 (for example, P2-41) on the hole transport layer. layer), a second light-emitting auxiliary layer (green light-emitting auxiliary layer) disposed in the second subpixel was formed. Thereafter, on the first and second light emitting auxiliary layers, the compounds of formulas 5 to 7 (for example, P3-51) are applied to the first to third subpixels that satisfy the thickness conditions of FIGS. 2 and 3. A third light-emitting auxiliary layer (blue light-emitting auxiliary layer) was formed.

As a host on top of the third light-emitting auxiliary layer, a first organic light-emitting layer (red organic light-emitting layer) disposed in the first subpixel, a second organic light-emitting layer (green organic light-emitting layer) disposed in the second subpixel, and a third subpixel. The organic emission layer including the third organic emission layer (blue organic emission layer) was deposited to a thickness of 400 nm. Subsequently, tris(8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was formed into a 300 nm thick film as an electron transport layer. Afterwards, LiF, an alkali metal halide, was deposited to a thickness of 5 nm as an electron injection layer, and then Al was deposited to a thickness of 150 nm and used as a cathode to manufacture an organic light emitting device.

[Comparative example]

An organic light emitting device was manufactured in the same manner as in the above example, except that Comparative Compounds 1 and 2 were used as the third light emitting auxiliary layer in the above-described method of manufacturing an organic light emitting device.

In addition, in the above-described method of manufacturing an organic light-emitting device, an organic light-emitting device was manufactured in the same manner as the above example, except that P2-41, which was used as the first and second light-emitting auxiliary layers as Comparative Compound 3, was used as the third light-emitting auxiliary layer. was manufactured. In this comparative example, the same compound was used as the third light-emitting auxiliary layer for the first and second light-emitting auxiliary layers, so an organic light-emitting device was manufactured by varying the thickness of the same compound.

A forward bias direct current voltage was applied to the organic light emitting devices manufactured according to the Examples and Comparative Examples of the present invention, and the electroluminescence (EL) characteristics were measured using Photoresearch's PR-650, and the measurement result was 5000 cd/m ² The T95 lifespan was measured using a lifespan measurement equipment manufactured by McScience at the standard luminance, and the measurement results were as shown in Table 1 (blue), Table 2 (green), and Table 3 (red) below. In this case, specific compounds P3-51 and P2-41 were shown as examples in the examples, but other compounds also showed similar measurement results. In Tables 1 to 3, Comparative Compound 3 (P2-41) corresponds to an organic light-emitting device in which the same compound was used as the third light-emitting auxiliary layer for the first and second light-emitting auxiliary layers, and only the thickness of the same compound was changed.

[Table 1]

[Table 2]

[Table 3]

Among the measurement results in Table 1 (blue), Table 2 (green), and Table 3 (red), the driving voltage, luminous efficiency, and lifespan are expressed graphically as shown in Figures 9 to 11. 9 to 11, the organic light emitting device of Comparative Compound 3 (P2-41) is shown as P2-41 as a comparative example.

As can be seen from the measurement results of FIGS. 9 to 11, the organic light-emitting device using the compound according to an embodiment of the present invention has significantly improved luminous efficiency and lifespan compared to the organic light-emitting device using Comparative Compound 1 and Comparative Compound 2. confirmed. In addition, an organic light-emitting device using a compound according to an embodiment of the present invention uses the same compound of the first and second light-emitting auxiliary layers as the third light-emitting auxiliary layer, and thus has higher luminous efficiency and lifespan than an organic light-emitting device with only a different thickness of the same compound. It was confirmed that this was significantly improved.

In particular, the compounds of Formulas 5 to 7 of the present invention, which are the third light emitting auxiliary layer materials commonly disposed in the first to third subpixels, are used to form a common electron blocking layer (EBL) of the red, green, and blue subpixels. It was confirmed that it can be used as a material and has a high lifespan improvement effect.

That is, the organic light emitting display device and its organic light emitting element according to the above-described embodiments have the effect of improving light emission performance (higher efficiency) and significantly improving lifespan (longer lifespan).

In the above, even though all the components constituting the embodiment of the present invention have been described as being combined or operated in combination, the present invention is not necessarily limited to this embodiment. That is, as long as it is within the scope of the purpose of the present invention, all of the components may be operated by selectively combining one or more of them. The above description is merely an illustrative explanation of the technical idea of the present invention, and various modifications and variations will be possible to those skilled in the art without departing from the essential characteristics of the present invention. The scope of protection of the present invention should be interpreted in accordance with the claims below, and all technical ideas within the equivalent scope should be construed as being included in the scope of rights of the present invention.

120: first electrode 130: hole injection layer
135: hole transport layer 140: light emitting auxiliary layer
145: organic light emitting layer 160: electron transport layer
170: electron injection layer 180: second electrode

Claims (25)

A substrate including a first subpixel in red, a second subpixel in green, and a third subpixel in blue;
a first electrode disposed on the substrate;
a second electrode disposed to face the first electrode;
It is disposed between the first electrode and the second electrode, and includes a first organic light emitting layer disposed in the first subpixel, a second organic light emitting layer disposed in the second subpixel, and a third layer disposed in the third subpixel. An organic light-emitting layer including an organic light-emitting layer;
a hole transport layer disposed between the first electrode and the organic light emitting layer; and
It is disposed between the hole transport layer and the organic light-emitting layer, and includes a first light-emitting auxiliary layer disposed in the first subpixel, a second light-emitting auxiliary layer disposed in the second subpixel, and the first light-emitting layer between the hole transport layer and the organic light-emitting layer. and a third auxiliary light emitting layer disposed on the second auxiliary light emitting layer and commonly disposed in the first to third subpixels,
The third light-emitting auxiliary layer is an organic light-emitting device containing a compound represented by the following formula (5):
[Formula 5]

In Formula 5 above,
1) R ₃ and R ₄ are each hydrogen, deuterium, C6-60 aryl group, C2-60 alkenyl group, C1-60 alkyl group, C6-60 aryloxy group, C2-60 hetero group containing N It is selected from the group consisting of cyclic group, cyano group, nitro group and halogen group,
2) n is an integer from 0 to 4, o is an integer from 0 to 3,
3) L is either a single bond or a C6-60 arylene group,
4) Ar ₉ and Ar ₁₀ are each an aryl group at C6-24, a heterocyclic group at C3-24 containing at least one heteroatom among O, N, and S, or a fluorenyl group,
5) When n is 2 or more, R ₃ can combine with each other to form a ring, and when o is 2 or more, R ₄ can combine with each other to form a ring,
In Formula 5, the aryl group, heterocyclic group, alkenyl group, alkyl group, aryloxy group, arylene group, and fluorenyl group (including spirofluorenyl group) are a C6-24 aryl group and a C2-24 heterocyclic group. , a C1-30 alkyl group, a C2-24 alkenyl group, a C6-24 aryloxy group, a fluorenyl group, a halogen group, a nitro group, and a cyano group. When each of these substituents is adjacent, they can combine with each other to form a ring. According to claim 1,
An organic light emitting device wherein the first light emitting auxiliary layer has a thickness greater than the second light emitting auxiliary layer. According to claim 2,
An organic light emitting device wherein the second light emitting auxiliary layer has a thickness greater than the third light emitting auxiliary layer. According to claim 1,
An organic light-emitting device wherein the HOMO (Highest Occupied Molecular Orbital) level of the third light-emitting auxiliary layer is greater than the HOMO level of the hole transport layer and smaller than the HOMO level of the first and second light-emitting auxiliary layers. According to claim 4,
The material of the hole transport layer and the first to third light emitting auxiliary layers is an organic light emitting device made of a tertiary amine or a compound containing a tertiary amine including fluorene. According to claim 5,
An organic light emitting device in which the hole transport layer and the first and second light emitting auxiliary layers include a compound represented by the following formula (1):
[Formula 1]

In Formula 1, L is a single bond, a C6-C60 arylene group, a fluorenylene group, or a C2-C60 heterocyclic group containing S, l and m are each integers of 0 or more, and R ₁ and R ₂ is any one of a C6-C60 aryl group, a C2-C60 heterocyclic group containing N, or an alkenyl group, and Ar ₁ and Ar ₂ are a C6-C60 aryl group, at least one of O, N, and S. It is either a C2-C60 heterocyclic group containing one heteroatom or a fluorene group, and X is either NR' or CR'R",
However, when When X is R'R", R' and R" are either a C6-C60 aryl group or a C1-C30 alkyl group,
The aryl group, heterocyclic group, alkenyl group, alkyl group, aryloxy group, fluorene group (including spirofluorene group), arylene group, and fluorenyl group (including spirofluorenyl group) are C6-24 aryl groups. , C2-24 heterocyclic group, C1-30 alkyl group, C2-24 alkenyl group, C6-24 aryloxy group, fluorenyl group, halogen group, nitro group, cyano group. It may be further substituted with a substituent, and when each of these substituents is adjacent, they may combine with each other to form a ring. According to claim 6,
The formula 1 is an organic light-emitting device comprising a compound represented by the following formulas 2 to 4:
[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4,
L is any one of a C6-C60 arylene group, a fluorene group, or a C2-C60 heterocyclic group containing S, and Ar ₃ and Ar ₄ are at least one of a C6-C60 aryl group, O, N, and S. is either a C2-C60 heterocyclic group or a fluorene group containing a heteroatom, and Ar ₅ to Ar ₈ are a C6-C60 aryl group, C2 containing at least one heteroatom among O, N, and S. - Either a heterocyclic group or a fluorene group at C60,
However, in Formula 2, R' is any one of a C6-C60 aryl group, a C2-C60 heterocyclic group containing at least one heteroatom among O, N, and S, or a C1-C30 alkyl group, Formula 3 In, R' and R" are either a C6-C60 aryl group or a C1-C30 alkyl group,
When Ar ₃ and Ar ₄ are C2-C60 heterocyclic groups, carbazole is included, and when Ar ₅ to Ar ₈ are C6-C60 heterocyclic groups, carbazole is not included. According to claim 5,
An organic light emitting device wherein the first and second light emitting auxiliary layers are made of the same compound, and the hole transport layer is a different compound. According to claim 7,
The first and second light emitting auxiliary layers are a compound represented by Formula 3 or Formula 4, and the hole transport layer is a compound represented by Formula 2. delete According to claim 1,
The formula (5) is an organic light emitting device comprising compounds represented by the following formulas (6) and (7):
[Formula 6]

[Formula 7]

In Formulas 6 and 7, R ₃ , R ₄ , n, o, Ar ₉ and Ar ₁₀ are the same as defined for R ₃ , R ₄ , n, o, Ar ₉ and Ar ₁₀ in claim 1. According to claim 6,
The compound represented by the formula 1 is a compound represented by one of the formulas P1-1 to P1-77 and P2-1 to P2-72, and the compound represented by the formula 5 is a compound represented by the formula P3-1 to P3-80 below. Organic light-emitting devices that are compounds represented by one:

. A substrate containing two or more subpixels;
a first electrode disposed on the substrate;
a second electrode disposed to face the first electrode;
Organic light emitting layers of different colors disposed in each of two or more subpixels between the first electrode and the second electrode;
a hole transport layer disposed between the first electrode and the organic light emitting layer; and
It is disposed between the hole transport layer and the organic light-emitting layer, one or more individual light-emitting auxiliary layers respectively disposed in some of the two or more subpixels, and disposed on the individual light-emitting auxiliary layer between the hole transport layer and the organic light-emitting layer, It includes a common auxiliary light emitting layer commonly disposed in two or more subpixels,
At least one of the two or more subpixels is a blue subpixel, and the common auxiliary light emitting layer is a light emitting auxiliary layer of the blue subpixel,
The common light-emitting auxiliary layer is an organic light-emitting device containing a compound represented by the following formula (5):
[Formula 5]

In Formula 5 above,
1) R ₃ and R ₄ are each hydrogen, deuterium, C6-60 aryl group, C2-60 alkenyl group, C1-60 alkyl group, C6-60 aryloxy group, C2-60 hetero group containing N It is selected from the group consisting of cyclic group, cyano group, nitro group and halogen group,
2) n is an integer from 0 to 4, o is an integer from 0 to 3,
3) L is either a single bond or a C6-60 arylene group,
4) Ar ₉ and Ar ₁₀ are each an aryl group at C6-24, a heterocyclic group at C3-24 containing at least one heteroatom among O, N, and S, or a fluorenyl group,
5) When n is 2 or more, R ₃ can combine with each other to form a ring, and when o is 2 or more, R ₄ can combine with each other to form a ring,
In Formula 5, the aryl group, heterocyclic group, alkenyl group, alkyl group, aryloxy group, arylene group, and fluorenyl group (including spirofluorenyl group) are a C6-24 aryl group and a C2-24 heterocyclic group. , a C1-30 alkyl group, a C2-24 alkenyl group, a C6-24 aryloxy group, a fluorenyl group, a halogen group, a nitro group, and a cyano group. When each of these substituents is adjacent, they can combine with each other to form a ring. According to claim 13,
There are 2 to 4 subpixels,
The organic light emitting layer includes 2 to 4 organic light emitting layers each arranged in 2 to 4 subpixels,
The light emitting auxiliary layer is an organic light emitting device comprising a common light emitting auxiliary layer commonly disposed in the 2 to 4 subpixels and 1 to 3 individual light emitting auxiliary layers respectively disposed in 1 to 3 subpixels. Driving transistors disposed in each of the first, second, and third subpixels that emit different colors; and
An organic light emitting display device electrically connected to the driving transistor and comprising the organic light emitting device of claim 1. According to claim 15,
The organic light emitting display device wherein the first light emitting auxiliary layer has a thickness greater than the second light emitting auxiliary layer. According to claim 15,
The organic light emitting display device wherein the second light emitting auxiliary layer has a thickness greater than the third light emitting auxiliary layer. According to claim 15,
An organic light emitting display device wherein the highest occupied molecular orbital (HOMO) level of the third light emitting auxiliary layer is greater than the HOMO level of the hole transport layer and smaller than the HOMO level of the first and second light emitting auxiliary layers. According to claim 18,
The material of the hole transport layer and the first to third light emitting auxiliary layers is an organic light emitting display device made of a tertiary amine or a compound containing a tertiary amine including fluorene. delete delete delete delete delete delete

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