KR20220083371A - Organic electroluminescent compound prepared from quinone and method for manufacturing the same - Google Patents

Abstract

An organic light emitting compound prepared from a quinone-based material and a method for preparing the same, wherein the organic light emitting compound has excellent solvent resistance, and an organic light emitting device comprising the same is characterized in that it exhibits excellent electroluminescence properties.

Description

Organic light emitting compound prepared from quinone-based material and method for manufacturing the same

The present invention relates to an organic light emitting compound prepared from a quinone-based material and a method for preparing the same, wherein the organic light emitting compound has excellent solvent resistance, and an organic light emitting device comprising the same is characterized in that it exhibits excellent electroluminescence properties.

The organic light emitting device is a device that emits light while electrons and holes are paired and then extinguished when electric charges are injected into an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode). Not only can devices be formed on a flexible transparent substrate such as plastic, but it can be driven at a lower voltage (10V or less) compared to plasma display panels or inorganic EL displays, and power consumption is reduced. It is relatively small and has the advantage of excellent color.

A typical organic light emitting device includes a substrate, an anode, a hole injection layer that receives holes from the anode, a hole transport layer that transports holes, a light emitting layer that emits light by combining holes and electrons, an electron transport layer that receives electrons from the cathode and transfers them to the light emitting layer, and It consists of a cathode. In some cases, the light emitting layer may be configured by doping a small amount of fluorescent or phosphorescent dye into the electron transport layer or hole transport layer without a separate light emitting layer. of polymers can be performed simultaneously. The organic thin film layers between the two electrodes are formed by vacuum deposition, spin coating, inkjet printing, roll coating, or the like, and a separate electron injection layer is sometimes inserted for efficient injection of electrons from the cathode.

The most important factor determining the luminous efficiency in an organic light emitting device is the light emitting material. Fluorescent materials are currently widely used as light-emitting materials, but development of phosphorescent materials is one of the best ways to theoretically improve light-emitting efficiency up to 4 times due to the light-emitting mechanism. Until now, the iridium(III) complex series is widely known as phosphorescent materials, and materials such as (acac)Ir(btp)2, Ir(ppy)3 and Firpic are known for each RGB. CBP is the most widely known phosphorescent host material so far, and high-efficiency OLEDs to which hole blocking layers such as BCP and BAlq are applied are known. there is a bar

However, an organic electroluminescent device using a conventional phosphorescent material has significantly higher current efficiency (cd/A) than a device using a fluorescent material, but when a material such as BAlq or CBP is used as a host of the phosphorescent material, the Since the driving voltage is high compared to the device using .

Accordingly, the present inventors synthesized a novel organic light-emitting compound prepared from a quinone-based material while researching to solve the above problems, and when used as a host material for an organic light-emitting device, excellent stability and electroluminescence properties It was found that the present invention was completed.

In this regard, Korean Patent Registration No. 10-1536181 discloses an organic light emitting compound and an organic optical device using the same.

The present invention has been devised to solve the problems of the prior art, and an object of the present invention is to provide a novel organic light emitting compound.

Another object of the present invention is to provide an organic light emitting device including the organic light emitting compound as a light emitting layer.

Another object of the present invention is to provide a method for preparing the novel organic light emitting compound.

As a technical means for achieving the above-described technical problem, one aspect of the present invention is,

An organic light emitting compound represented by the following Chemical Formula 1 or Chemical Formula 2 is provided.

[Formula 1]

In Formula 1, R1 and R2 are each independently linear or branched C1-C20 alkyl, linear or branched C2-C20 alkenyl, C3-C20 cycloalkyl or C6-C30 aryl, R3 and R4 are each independently straight or branched C1-C20 alkyl or straight or branched C2-C20 alkenyl, R5 and R6 are each independently straight or branched C1-C20 alkyl, straight or branched C2-C20 al kenyl, C3-C20 cycloalkyl or C6-C30 aryl.

[Formula 2]

In Formula 2, R1 and R2 are each independently linear or branched C1-C20 alkyl, straight or branched C2-C20 alkenyl, C3-C20 cycloalkyl or C6-C30 aryl, R3 and R4 are each independently straight-chain or branched C1-C20 alkyl or straight-chain or branched C2-C20 alkenyl.

In Formula 1, R1 and R2 are each independently linear or branched C1-C20 alkyl or linear or branched C2-C20 alkenyl, and R3 and R4 are each independently linear or branched C1-C20 alkyl. and R5 and R6 are each independently linear or branched C1-C20 alkyl or linear or branched C2-C20 alkenyl, and in Formula 2, R1 and R2 are each independently linear or branched C1-C20 C20 alkyl or linear or branched C2-C20 alkenyl, and R3 and R4 may each independently be linear or branched C1-C20 alkyl.

In Formula 1, R1 and R2 are each independently linear or branched C2-C20 alkenyl, R3 and R4 are each independently linear or branched C1-C10 alkyl, and R5 and R6 are each independently linear or branched straight-chain or branched C2-C20 alkenyl, in Formula 2, R1 and R2 are each independently straight-chain or branched C2-C20 alkenyl, and R3 and R4 are each independently straight-chain or branched It may be a C1-C10 alkyl chain.

In Formula 1, R1 and R2 are each independently linear or branched C2-C10 alkenyl, R3 and R4 are each independently linear or branched C1-C5 alkyl, R5 and R6 are each independently linear or branched straight-chain or branched C2-C10 alkenyl, in Formula 2, R1 and R2 are each independently straight-chain or branched C2-C10 alkenyl, and R3 and R4 are each independently straight-chain or branched It may be a C1-C5 alkyl chain.

In Formula 1, R1 and R2 are straight-chain C5 alkenyl, R3 and R4 are straight-chain C3 alkyl, R5 and R6 are straight-chain C5 alkenyl, and in Formula 2, R1 and R2 are straight-chain C5 alkenyl, and R3 and R4 may be straight-chain C3 alkyl.

In addition, another aspect of the present invention,

It provides an organic light emitting device comprising the organic light emitting compound as a light emitting layer.

In addition, another aspect of the present invention,

As a method for producing an organic light emitting compound represented by Formula 1 or Formula 2, the organic light emitting compound represented by Formula 1 is prepared through the following Reaction Scheme 1, and the organic light emitting compound represented by Formula 2 is prepared through the following Reaction Scheme 2 It provides a method for producing an organic light emitting compound that is.

[Scheme 1]

In Scheme 1, R1 and R2 are each independently straight or branched C1-C20 alkyl, straight or branched C2-C20 alkenyl, C3-C20 cycloalkyl or C6-C30 aryl, and R3 and R4 are each independently straight-chain or branched C1-C20 alkyl or straight-chain or branched C2-C20 alkenyl, and X is a halogen element.

[Scheme 2]

In Scheme 2, R1 and R2 are each independently linear or branched C1-C20 alkyl, straight or branched C2-C20 alkenyl, C3-C20 cycloalkyl or C6-C30 aryl, and R3 and R4 are each independently straight-chain or branched C1-C20 alkyl or straight-chain or branched C2-C20 alkenyl, and X is a halogen element.

The organic light emitting compound according to the present invention as described above may be very stable because of its high resistance to solvents.

In addition, when the organic light emitting compound is applied to an organic light emitting device, it exhibits excellent electroluminescence characteristics and exhibits excellent performance in terms of current efficiency (cd/A) and power efficiency (Im/W). It may be very suitable.

1 is a graph showing the MS spectrum of the organic light emitting compound prepared according to one preparation example of the present invention.
2 is a graph showing the MS spectrum of the organic light-emitting compound prepared according to another preparation example of the present invention.

Hereinafter, the present invention will be described in more detail. However, the present invention may be embodied in various different forms, and the present invention is not limited by the embodiments described herein, and the present invention is only defined by the claims to be described later.

In addition, the terms used in the present invention are only used to describe specific embodiments, and are not intended to limit the present invention. The singular expression includes the plural expression unless the context clearly dictates otherwise. In the entire specification of the present invention, 'including' any component means that other components may be further included, rather than excluding other components, unless otherwise stated.

The first aspect of the present application is

An organic light emitting compound represented by Formula 1 or Formula 2 is provided.

The second aspect of the present application is

It provides an organic light emitting device comprising the organic light emitting compound as a light emitting layer.

Hereinafter, the organic light emitting compound according to the first aspect of the present application and the organic light emitting device according to the second aspect of the present application will be described in detail.

In one embodiment of the present application, the organic light emitting compound represented by Formula 1 may have a structure as follows.

[Formula 1]

In Formula 1, R1 and R2 are each independently linear or branched C1-C20 alkyl, linear or branched C2-C20 alkenyl, C3-C20 cycloalkyl or C6-C30 aryl, R3 and R4 are each independently straight or branched C1-C20 alkyl or straight or branched C2-C20 alkenyl, R5 and R6 are each independently straight or branched C1-C20 alkyl, straight or branched C2-C20 al kenyl, C3-C20 cycloalkyl or C6-C30 aryl.

Preferably, in Formula 1, R1 and R2 are each independently linear or branched C1-C20 alkyl or linear or branched C2-C20 alkenyl, and R3 and R4 are each independently linear or branched C1-C20 and C20 alkyl, and R5 and R6 may each independently be a straight-chain or branched C1-C20 alkyl or a straight-chain or branched C2-C20 alkenyl.

More preferably, in Formula 1, R1 and R2 are each independently linear or branched C2-C20 alkenyl, R3 and R4 are each independently linear or branched C1-C10 alkyl, and R5 and R6 are each Independently, it may be a straight-chain or branched-chain C2-C20 alkenyl.

Even more preferably, in Formula 1, R1 and R2 are each independently linear or branched C2-C10 alkenyl, R3 and R4 are each independently linear or branched C1-C5 alkyl, and R5 and R6 are Each is independently linear or branched C2-C10 alkenyl, and in Formula 2, R1 and R2 may each independently be linear or branched C2-C10 alkenyl.

Most preferably, in Formula 1, R1 and R2 are straight-chain C5 alkenyl, R3 and R4 are straight-chain C3 alkyl, and R5 and R6 may be straight-chain straight-chain C5 alkenyl, an embodiment of the present invention According to , the compound represented by Formula 1 may have a structure of Formula 3 below.

[Formula 3]

In one embodiment of the present application, the organic light emitting compound represented by Formula 2 may have a structure as follows.

[Formula 2]

In Formula 2, R1 and R2 are each independently linear or branched C1-C20 alkyl, straight or branched C2-C20 alkenyl, C3-C20 cycloalkyl or C6-C30 aryl, R3 and R4 are each It may independently be a straight-chain or branched C1-C20 alkyl or a straight-chain or branched C2-C20 alkenyl.

Preferably, in Formula 2, R1 and R2 are each independently a linear or branched C1-C20 alkyl or a linear or branched C2-C20 alkenyl, and R3 and R4 are each independently a linear or branched C1-C20 C20 alkyl.

More preferably, in Formula 2, R1 and R2 may each independently be a linear or branched C2-C20 alkenyl, and R3 and R4 may each independently be a linear or branched C1-C10 alkyl.

Even more preferably, in Formula 2, R1 and R2 may each independently be a linear or branched C2-C10 alkenyl, and R3 and R4 may each independently be a linear or branched C1-C5 alkyl.

Most preferably, in Formula 2, R1 and R2 are straight-chain C5 alkenyl, R3 and R4 may be straight-chain C3 alkyl, and according to an embodiment of the present invention, the compound represented by Formula 2 is It may have a structure of 4.

[Formula 4]

In one embodiment of the present application, the organic light emitting compound represented by Formula 1 or 2 may have very excellent solvent resistance after thermal curing. Specifically, the organic light-emitting compound in the form of a thin film prepared by thermal curing after application on a substrate may have an elution degree of less than 15%, preferably less than 10%, when dipping into a solvent. The degree of dissolution may vary depending on the type of solvent, and the solvent may be, for example, isopropyl alcohol, toluene, or chlorobenzene.

In one embodiment of the present application, the organic light emitting device may include the organic light emitting compound represented by Formula 1 or 2 as a light emitting layer. In this case, the organic light emitting device may include a substrate, an electrode, a hole injection layer, a hole transport layer, a light emitting layer and an electron injection layer, and the organic light emitting compound may be one used in the organic material layer of the organic light emitting device due to its structural specificity. and, specifically, may be included as a host compound in the light emitting layer in the organic material layer.

Meanwhile, the organic light emitting device including the organic light emitting compound may have an efficiency (cd/A) of 50 to 70, and a power efficiency (lm/W) of 25 to 32. Accordingly, the organic light emitting device may have excellent light emitting characteristics by including the organic light emitting compound.

The third aspect of the present application is

As a method for preparing the organic light emitting compound represented by Formula 1 or Formula 2 according to the first aspect of the present application, the organic light emitting compound represented by Formula 1 is prepared through Scheme 1, and the organic light emitting compound represented by Formula 2 It provides a method for preparing an organic light emitting compound that is prepared through Scheme 2.

Although detailed descriptions of parts overlapping with the first and second aspects of the present application are omitted, the descriptions of the first and second aspects of the present application may be equally applied even if the description is omitted in the third aspect. .

Hereinafter, the method for preparing the organic light emitting compound according to the third aspect of the present application will be described in detail step by step.

In one embodiment of the present application, the organic light emitting compound represented by Formula 1 may be prepared through the following Reaction Scheme 1.

[Scheme 1]

In Scheme 1, R1 and R2 are each independently straight or branched C1-C20 alkyl, straight or branched C2-C20 alkenyl, C3-C20 cycloalkyl or C6-C30 aryl, and R3 and R4 are each independently straight or branched C1-C20 alkyl or straight or branched C2-C20 alkenyl, and X may be a halogen element.

In this case, since R1 to R4 have been described in detail in the first aspect of the present application, a detailed description will be omitted, and X may be Cl, Br, etc. as a halogen element, preferably Br.

In one embodiment of the present application, the organic light emitting compound represented by Formula 2 may be prepared through the following Reaction Scheme 2.

[Scheme 2]

In Scheme 2, R1 and R2 are each independently linear or branched C1-C20 alkyl, straight or branched C2-C20 alkenyl, C3-C20 cycloalkyl or C6-C30 aryl, and R3 and R4 are each independently straight or branched C1-C20 alkyl or straight or branched C2-C20 alkenyl, and X may be a halogen element.

In this case, since R1 to R4 have been described in detail in the first aspect of the present application, a detailed description will be omitted, and X may be Cl, Br, etc. as a halogen element, preferably Br.

Hereinafter, embodiments of the present invention will be described in detail so that those of ordinary skill in the art can easily carry out the present invention. However, the present invention may be embodied in several different forms and is not limited to the embodiments described herein.

production example 1. Preparation of organic light-emitting compound 1

An organic light emitting compound represented by Chemical Formula 1-7 was prepared through Scheme 3 below.

[Scheme 3]

1. Preparation of compound 1-1

First, 50 g (471 mmol) of benzaldehyde and 62.2 g (471 mmol) of 2,3-dihydroindene-1-one were put in a 2,000 mL three-necked round-bottom flask, dissolved in 500 mL of ethanol, and then at 0°C. 37.7 g (942 mmol) of sodium hydroxide was slowly added, and the mixture was stirred at room temperature for 12 hours. After cooling, the precipitated solid was separated by filtration under reduced pressure and washed with methanol to obtain Compound 1-1, 93.4 g (yield 90%) as a pale yellow solid compound.

2. Preparation of compound 1-3

3000 mL of pyridine was added to a 2,000 mL three-necked round-bottom flask, and 50 g (179 mmol) of 4-bromophenacyl bromide was slowly added while stirring. After stirring at room temperature for 2 hours, the precipitated solid was separated by filtration under reduced pressure and washed with methanol. After filtration, 44.1 g (159 mmol) of the obtained solid and the obtained compound 1-1, 32 g (144 mmol) and 77.3 g (55.7 mmol) of ammonium acetate were added, dissolved in 320 mL of methanol, and refluxed for 12 hours. . After cooling, the precipitated solid was separated by filtration under reduced pressure and washed with methanol to obtain Compound 1-3, 31 g (yield 55%) as a white solid compound.

3. Preparation of compound 1-4

Compound 1-3, 24 g (61 mmol) obtained above was placed in a 1,000 mL three-necked round-bottom flask, and 10 g (126 mmol) of 5-bromo-1-pentene was added thereto. Then, 240 mL of dimethyl sulfoxide was added. 10.1 g (183 mmol) of potassium hydroxide crushed with a mortar was put into the reactor, and the mixture was heated and stirred at 80° C. for 9 hours. After completion of the reaction, the temperature of the reactant was cooled to room temperature, 300 mL of distilled water and 300 mL of ethyl acetate were added for extraction, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. After concentration, the obtained residue was separated by a silica gel column (hexane:ethyl acetate=15:1) to obtain 16.09 g (yield 50%) of Compound 1-4 as a pale yellow solid.

4. Preparation of compound 1-5

Compound 1-4 obtained above in a 500 mL 3-neck round-bottom flask. After adding 15 g (28 mmol), 15.65 g (61 mmol) of bis (pinacolato) dibron, 190 mL of 1,4-dioxane was added. Then, 0.46 g (0.5 mmol) of 1,1'bis[(diphenylphosphino)ferrocene]dichloropalladium(II)chloromethane complex was added, and potassium acetate 5.5g (56mmol) was added thereto, followed by heating and stirring under reflux. . After 12 hours of reaction, the reactant was cooled to room temperature, and extracted with distilled water and ethyl acetate. Then, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. After concentration, the obtained residue was separated by a silica gel column (hexane:ethyl acetate=20:1) to obtain 9.9 g (yield 61%) of Compound 1-5 as a white solid.

5. Preparation of compounds 1-6

25 g (93.3 mmol) of 2,5-dibromohydroquinone was placed in a 1,000 mL three-necked round-bottom flask, and 250 mL of acetonitrile was added. Then, put 1-(3-bromopropoxy)-4-vinylbenzene 25 g (93.3 mmol), potassium carbonate 38.7 g (280 mmol), potassium iodide 7.75 g (47 mmol), respectively, Heat reaction was carried out for 30 hours.

The reaction product was cooled to room temperature, extracted with distilled water and ethyl acetate, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. After concentration, the obtained residue was separated by a silica gel column (hexane:ethyl acetate=50:1) to obtain 21 g (yield 38%) of compound 1-6 as a liquid product.

6. Preparation of compound 1-7

Compound 1-6 obtained above in a 1,000 mL three-necked round bottom flask. 10g (17mmol), Compound 1-5, 21.7g (37.4mmol) was added, and 1,4-dioxane 200mL was added. Then, 0.98 g (0.8 mmol) of tetrakis(triphenylphosphine)palladium(0) was added, 150 mL of a 2M aqueous potassium carbonate solution was added, and the mixture was heated and stirred at 80°C for 16 hours.

The reaction product was cooled to room temperature, extracted with distilled water and methylene chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. After concentration, the obtained residue was separated by a silica gel column (hexane:ethyl acetate=30:1) to obtain 7.9 g (yield 35%) of compound 1-7 as a solid product. MS:[M+H] 1336.6

The MS spectrum of the obtained compound 1-7 is shown in FIG. 1 .

¹ H NMR (CDCl3) δ[ppm] 7.92 - 7.86 (m, 4H), 7.85 (s, 2H), 7.75 (d, 2H), 7.57 - 7.52 (m, 4H), 7.52 - 7.48 (m, 4H) , 7.46 (t, 2H), 7.41 - 7.29 (m, 12H), 7.29 - 7.23 (m, 2H), 7.13 (s, 2H), 6.92 - 6.84 (m, 4H), 6.71 (t, 2H), 5.75 (t, 6.2 Hz, 4H), 5.65 (d, 4H), 5.11 - 4.98 (m, 8H), 4.26 - 4.06 (m, 8H), 2.20 (m, 4H), 2.11 (q, 8H), 1.97 ( t, 8H), 1.48 (d, 8H).

production example 2. Preparation of organic light-emitting compound 2

An organic light emitting compound represented by Chemical Formula 1-9 was prepared through Scheme 4 below. In this case, compounds 1-5 and 1-6 were prepared in the same manner as in Preparation Example 1.

[Scheme 4]

1. Preparation of compounds 1-8

Compound 1-6, 10g (17 mmol) and Compound 1-5, 9.9 g (17 mmol) were placed in a 1,000 mL 3-neck round bottom flask, and 200 mL of 1,4-dioxane was added. Then, 0.98 g (0.8 mmol) of tetrakis (triphenylphosphine) palladium (0) was added, and 150 mL of a 1 M aqueous potassium carbonate solution was added, followed by heating and stirring at 80° C. for 12 hours.

The reaction product was cooled to room temperature, extracted with distilled water and ethyl acetate, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. After concentration, the obtained residue was separated by a silica gel column (hexane:ethyl acetate=50:1) to obtain a solid product of Compound 1-8, 6.5 g (yield 40%).

2. Preparation of compounds 1-9

Compound 1-8, 5 g (5.2 mmol) and 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-) in a 1,000 mL 3-neck round bottom flask 2-Nyl)-9H-carbazole 2.01 g (5.5 mmol) was added, and 200 mL of 1,4-dioxane was added thereto. Then, 0.3 g (0.3 mmol) of tetrakis (triphenylphosphine) palladium (0) was added, and 100 mL of a 2 M aqueous potassium carbonate solution was added, followed by heating and stirring at 80° C. for 12 hours.

The reaction product was cooled to room temperature, extracted with distilled water and ethyl acetate, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. After concentration, the obtained residue was separated by a silica gel column (hexane:ethyl acetate=20:1) to obtain a solid product of Compound 1-9, 2.05 g (yield 35%). MS:[M+H] 1125.4

The MS spectrum of the obtained compound 1-9 is shown in FIG. 2 .

¹ H NMR (CDCl3) δ [ppm]: 8.12 (d, 1H), 8.09 (d, 1H), 7.92 (d, 1H), 7.90 - 7.84 (m, 3H), 7.76 (s, 1H), 7.74 - 7.69 (m, 2H), 7.66 - 7.59 (m, 5H), 7.58 - 7.49 (m, 3H), 7.49 - 7.28 (m, 11H), 7.27 - 7.17 (m, 4H), 6.93 - 6.83 (m, 4H) ), 6.76 - 6.65 (m, 2H), 5.75 (t, 2H), 5.62 (d, 4H), 5.04 (d, 4H), 4.21 - 4.12 (m, 8H), 2.20 (m, 4H), 2.11 ( q, 4H), 2.06 (t, 4H), 1.47 (d, 4H).

Example 1. Manufacture of organic light emitting device

A glass substrate with a size of 25 mm x 25 mm x 0.7 mm having an ITO (indium tin oxide) transparent electrode line with a thin film thickness of 150 nm was ultrasonically cleaned in distilled water dissolved in detergent for 20 minutes, followed by 10 minutes using isopropyl alcohol. was washed once. After cleaning with isopropyl alcohol, the substrate was again ultrasonically cleaned for 10 minutes each using distilled water and dried. Then, oxygen/nitrogen plasma was treated in a vacuum deposition equipment for 2 minutes.

After the plasma operation of the substrate is finished, the substrate is vacuum-adsorbed to the spin coater equipment to manufacture a device for solution processing, and then PEDOT:PSS, a polythiophene derivative, as a conductive polymer to cover the transparent electrode on the surface on which the transparent electrode line is formed. was diluted with isopropyl alcohol, spin-coated at 2,000 rpm for 1 minute, and dried on a hot plate at 130° C. for 30 minutes to produce a thin film with a thickness of 50 nm and used as a hole injection layer.

PVK (poly-N-vinylcarbazole) was diluted in toluene on the hole injection layer and spin-coated at 2,000 rpm for 30 seconds, dried on a hot plate at 130° C. for 30 minutes, and then a hole transport layer of 15 nm was formed.

As a dopant, a solution in which AYPD, which is an iridium-based complex, was dissolved in chlorobenzene at 0.5 wt% (Dopant) and as a host, a solution in which the organic light emitting compound 1-7 prepared in Preparation Example 1 was dissolved in toluene at 1 wt% (HOST) was mixed in a volume ratio of 5 (Dopant):95 (HOST) and spin-coated on the hole transport layer at 2,000 rpm for 30 seconds, and then cross-linked on a hot plate at 160° C. for 35 minutes to form a light emitting layer with a thickness of 30 nm.

On the light emitting layer, TSP01 (diphenyl-4-triphenylsilylphenylphosphine oxide) and TPBI (1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene) were deposited as an electron transport layer with a thickness of 25 mm, and then Liq ( Lithiumquinolate) was deposited to form an electron injection layer with a thickness of 1 nm. Finally, metal aluminum was deposited on the Liq film to form a metal cathode, thereby manufacturing an organic light emitting diode.

Example 2. Manufacture of organic light emitting device

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 1-9 prepared in Preparation Example 2 was used as a host material.

Experimental example 1. Solvent resistance evaluation

The solvent resistance of the organic light emitting compounds prepared in Preparation Examples 1 and 2, respectively, was evaluated. To this end, first, a glass substrate (25mm X 25mm X 0.7mm) was ultrasonically washed for 10 minutes in distilled water in which detergent was dissolved, and washed twice with distilled water for 10 minutes repeatedly. After cleaning with distilled water, the substrate was sequentially ultrasonically cleaned for 10 minutes using a solvent of isopropyl alcohol, acetone, and methanol and dried.

A liquid composition was prepared by dissolving the organic light-emitting compound prepared in Preparation Examples 1 and 2 in toluene at 1 wt %, respectively. Each of the prepared liquid compositions was applied on a glass substrate mounted on a spin coater, a primary thin film was formed at 500 rpm for 15 sec, and a secondary thin film was formed at 1,000 rpm for 30 sec. Then, the films on the glass substrate were baked at 160° C. for 35 minutes each using a hot plate in a glove box substituted with nitrogen, and then the films on the glass substrate were cooled to room temperature. After dipping the glass substrate on which the film was formed in isopropyl alcohol, toluene, and chlorobenzene, respectively, the resistance to the solvent of the thin film was measured through UV measurement. The results are shown in Table 1 below.

[Table 1]

As shown in Table 1, it was confirmed that the organic light emitting compound prepared according to the preparation example of the present invention had very good resistance to solvent.

Experimental example 2. Evaluation of electroluminescence properties

The electroluminescence characteristics of the organic light emitting diodes prepared in Examples 1 and 2 were measured, and the results are shown in Table 2 below.

[Table 2]

As shown in Table 2, the organic light emitting device manufactured according to the embodiment of the present invention includes the organic light emitting compound prepared according to the preparation example in the light emitting layer, thereby confirming that it has very excellent light emitting characteristics in terms of current efficiency and power efficiency. could

Above, the present invention has been described in detail with preferred embodiments with reference to the drawings, but the scope of the technical idea of the present invention is not limited to these drawings and examples. Accordingly, various modifications or equivalent ranges of embodiments may exist within the scope of the technical spirit of the present invention. Therefore, the scope of the technical idea according to the present invention should be interpreted by the claims, and the technical idea within the equivalent or equivalent scope should be interpreted as belonging to the scope of the present invention.

Claims (7)

An organic light emitting compound represented by the following Chemical Formula 1 or Chemical Formula 2:
[Formula 1]

(In Formula 1,
R1 and R2 are each independently linear or branched C1-C20 alkyl, straight or branched C2-C20 alkenyl, C3-C20 cycloalkyl or C6-C30 aryl;
R3 and R4 are each independently linear or branched C1-C20 alkyl or straight or branched C2-C20 alkenyl;
R5 and R6 are each independently straight or branched C1-C20 alkyl, straight or branched C2-C20 alkenyl, C3-C20 cycloalkyl or C6-C30 aryl.)

[Formula 2]

(In Formula 2,
R1 and R2 are each independently linear or branched C1-C20 alkyl, straight or branched C2-C20 alkenyl, C3-C20 cycloalkyl or C6-C30 aryl;
R3 and R4 are each independently straight or branched C1-C20 alkyl or straight or branched C2-C20 alkenyl.)
The method of claim 1,
In Formula 1, R1 and R2 are each independently linear or branched C1-C20 alkyl or linear or branched C2-C20 alkenyl;
R3 and R4 are each independently a linear or branched C1-C20 alkyl;
R5 and R6 are each independently linear or branched C1-C20 alkyl or straight or branched C2-C20 alkenyl;
In Formula 2, R1 and R2 are each independently linear or branched C1-C20 alkyl or linear or branched C2-C20 alkenyl;
R3 and R4 are each independently a linear or branched C1-C20 alkyl of the organic light emitting compound.
The method of claim 1,
In Formula 1, R1 and R2 are each independently linear or branched C2-C20 alkenyl,
R3 and R4 are each independently linear or branched C1-C10 alkyl;
R5 and R6 are each independently a linear or branched straight-chain or branched C2-C20 alkenyl,
In Formula 2, R1 and R2 are each independently linear or branched C2-C20 alkenyl,
R3 and R4 are each independently a linear or branched C1-C10 alkyl of the organic light emitting compound.
The method of claim 1,
In Formula 1, R1 and R2 are each independently linear or branched C2-C10 alkenyl,
R3 and R4 are each independently linear or branched C1-C5 alkyl;
R5 and R6 are each independently linear or branched C2-C10 alkenyl,
In Formula 2, R1 and R2 are each independently linear or branched C2-C10 alkenyl,
R3 and R4 are each independently a linear or branched C1-C5 alkyl of the organic light emitting compound.
The method of claim 1,
In Formula 1, R1 and R2 are straight-chain C5 alkenyl,
R3 and R4 are straight-chain C3 alkyl,
R5 and R6 are straight-chain C5 alkenyl,
In Formula 2, R1 and R2 are straight-chain C5 alkenyl,
R3 and R4 are straight-chain C3 alkyl of the organic light emitting compound.
An organic light emitting device comprising the organic light emitting compound of claim 1 as a light emitting layer.
A method for producing an organic light emitting compound represented by Formula 1 or Formula 2 according to claim 1,
The organic light emitting compound represented by Formula 1 is prepared through the following Reaction Scheme 1,
The organic light emitting compound represented by Formula 2 is a method for preparing an organic light emitting compound which is prepared through the following Reaction Scheme 2:
[Scheme 1]

(In Scheme 1,
R1 and R2 are each independently linear or branched C1-C20 alkyl, straight or branched C2-C20 alkenyl, C3-C20 cycloalkyl or C6-C30 aryl;
R3 and R4 are each independently linear or branched C1-C20 alkyl or straight or branched C2-C20 alkenyl;
X is a halogen element.)

[Scheme 2]

(In Scheme 2,
R1 and R2 are each independently linear or branched C1-C20 alkyl, straight or branched C2-C20 alkenyl, C3-C20 cycloalkyl or C6-C30 aryl;
R3 and R4 are each independently linear or branched C1-C20 alkyl or straight or branched C2-C20 alkenyl;
X is a halogen element.)

Images