KR102526282B1 - Organic electroluminescent compound prepared from quinone and method for manufacturing the same - Google Patents

Abstract

It 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 including the organic light emitting compound exhibits excellent electroluminescent properties.

Description

Organic light-emitting compound prepared from quinone-based materials and its manufacturing method

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 including the organic light emitting compound exhibits excellent electroluminescent properties.

An organic light emitting device is a device that emits light while electrons and holes form pairs when charge is injected into an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode) and then disappears. Not only can devices be formed on flexible transparent substrates such as plastic, but they can be driven at a lower voltage (less than 10V) compared to plasma display panels or inorganic EL displays, and power consumption is low. 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 formed by doping the electron transport layer or the hole transport layer with a small amount of fluorescent or phosphorescent dye without a separate light emitting layer. of polymers can perform 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 in some cases, a separate electron injection layer is inserted for efficient injection of electrons from the cathode.

The most important factor determining luminous efficiency in an organic light emitting device is a light emitting material. Although fluorescent materials are currently widely used as light emitting materials, the development of phosphorescent materials is one of the best ways to theoretically improve luminous efficiency up to 4 times in terms of light emitting mechanism. Until now, iridium (III) complexes have been widely known as phosphorescence emitting 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 using hole blocking layers such as BCP and BAlq are known. Pioneer in Japan has developed high-performance OLEDs using BAlq derivatives as hosts. there is a bar

However, organic electroluminescent devices using existing phosphorescent emitting materials have significantly higher current efficiency (cd/A) than devices using fluorescent emitting materials, but when materials such as BAlq or CBP are used as a host for phosphorescent emitting materials, fluorescent materials There is no significant advantage in terms of power efficiency (lm/w) because the driving voltage is higher than that of devices using, and the lifespan of the device is not satisfactory, so the development of a more stable and high-performance host material is required. .

Accordingly, the inventors of the present invention synthesized a novel organic light-emitting compound prepared from a quinone-based material while studying to solve the above problems, and when used as a host material for an organic light-emitting device, excellent stability and electroluminescent properties It was discovered 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 made to solve the above problems of the prior art, and an object thereof is to provide a novel organic light emitting compound.

In addition, an object thereof is to provide an organic light emitting device including the organic light emitting compound as a light emitting layer.

In addition, the object is to provide a method for producing the novel organic light emitting compound.

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

Provided is an organic light emitting compound represented by Formula 1 or Formula 2 below.

[Formula 1]

In Formula 1, R1 and R2 are each independently a linear or branched C1-C20 alkyl, a linear or branched C2-C20 alkenyl, a C3-C20 cycloalkyl or a C6-C30 aryl, and R3 and R4 are each Independently represent linear or branched C1-C20 alkylene or linear or branched C2-C20 alkenylene, R5 and R6 are each independently linear or branched C1-C20 alkyl, linear or branched C2-C20 alkenyl, C3-C20 cycloalkyl or C6-C30 aryl.

[Formula 2]

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

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. Ren, 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 alkyl or straight or branched C2-C20 alkenyl, and R3 and R4 may each independently be straight or branched C1-C20 alkylene.

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 alkylene, and R5 and R6 are each independently Linear or branched straight 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 linear or branched It may be a branched C1-C10 alkylene.

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

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

In addition, another aspect of the present invention,

An organic light emitting device including the organic light emitting compound as a light emitting layer is provided.

In addition, another aspect of the present invention,

As a method for preparing the 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 will be.

[Scheme 1]

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

[Scheme 2]

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

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

In addition, when the organic light emitting compound is applied to an organic light emitting device, it exhibits excellent electroluminescent properties and exhibits excellent performance in terms of current efficiency (cd/A) and power efficiency (Im/W), making it suitable for application as a light emitting layer of an organic light emitting device. It can be very suitable.

1 is a graph showing an MS spectrum of an organic light emitting compound prepared according to a preparation example of the present invention.
Figure 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 can be implemented in many 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, terms used in the present invention are only used to describe specific embodiments, and are not intended to limit the present invention. Singular expressions include plural expressions unless the context clearly dictates otherwise. In the entire specification of the present invention, 'include' a certain element means that other elements may be further included without excluding other elements 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,

An organic light emitting device including the organic light emitting compound as a light emitting layer is provided.

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 Chemical Formula 1 may have a structure as follows.

[Formula 1]

In Formula 1, R1 and R2 are each independently a linear or branched C1-C20 alkyl, a linear or branched C2-C20 alkenyl, a C3-C20 cycloalkyl or a C6-C30 aryl, and R3 and R4 are each Independently represent linear or branched C1-C20 alkylene or linear or branched C2-C20 alkenylene, R5 and R6 are each independently linear or branched C1-C20 alkyl, linear or branched C2-C20 It can be alkenyl, 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 alkenyl. C20 alkylene, and R5 and R6 may each independently be straight-chain or branched-chain C1-C20 alkyl or 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 alkylene, and R5 and R6 are Each independently 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 alkylene, and R5 and R6 are each independently a straight-chain or branched-chain C2-C10 alkenyl, and in Formula 2, R1 and R2 may each independently represent a straight-chain or branched C2-C10 alkenyl.

Most preferably, in Formula 1, R1 and R2 are linear C5 alkenyl, R3 and R4 are linear C3 alkylene, and R5 and R6 may be linear C5 alkenyl. According to an example, the compound represented by Chemical Formula 1 may have a structure represented by Chemical Formula 3 below.

[Formula 3]

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

[Formula 2]

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

Preferably, in Formula 2, 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 alkenyl. It may be C20 alkylene.

More preferably, in Formula 2, R1 and R2 are each independently linear or branched C2-C20 alkenyl, and R3 and R4 are each independently linear or branched C1-C10 alkylene.

More preferably, in Formula 2, R1 and R2 are each independently linear or branched C2-C10 alkenyl, and R3 and R4 are each independently linear or branched C1-C5 alkylene.

Most preferably, in Formula 2, R1 and R2 may be linear C5 alkenyl, and R3 and R4 may be linear C3 alkylene. According to an embodiment of the present invention, the compound represented by Formula 2 has the following formula It may have a structure of 4.

[Formula 4]

In one embodiment of the present application, the organic light-emitting compound represented by Chemical Formula 1 or 2 may have excellent solvent resistance after thermal curing. Specifically, the organic light-emitting compound in the form of a thin film prepared by being applied on a substrate and then thermally cured may have a dissolution degree of less than 15%, preferably less than 10%, when dipping into a solvent. The degree of elution 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 an organic light emitting compound represented by Chemical 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 used in an organic material layer of the organic light emitting device due to its structural specificity. And, specifically, it 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 producing 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 Reaction Formula 1, and the organic light emitting compound represented by Formula 2 Provides a method for producing an organic light emitting compound that is prepared through Scheme 2.

Detailed descriptions of portions overlapping with the first and second aspects of the present application have been omitted, but the contents described for the first and second aspects of the present application can 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 Chemical Formula 1 may be prepared through Reaction Scheme 1 below.

[Scheme 1]

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

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

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

[Scheme 2]

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

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

Hereinafter, embodiments of the present invention will be described in detail so that those skilled in the art can easily implement the present invention. However, the present invention may be embodied in many different forms and is not limited to the embodiments described herein.

manufacturing example 1. Preparation of organic light-emitting compounds 1

An organic light-emitting compound represented by Chemical Formulas 1-7 was prepared through Reaction 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-dihydroinden-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 thereto, 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 93.4 g (90% yield) of Compound 1-1 as a pale yellow solid compound.

2. Preparation of compounds 1-3

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

3. Preparation of compounds 1-4

24 g (61 mmol) of compound 1-3 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 crushed potassium hydroxide was added to the reactor, and heated and stirred at 80° C. for 9 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with 300 mL of distilled water and 300 mL of ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. After concentration, the obtained residue was separated with a silica gel column (hexane : ethyl acetate = 15:1) to obtain 16.09 g (50% yield) of Compound 1-4 as a pale yellow solid.

4. Preparation of compounds 1-5

Compounds 1-4 obtained above were placed in a 500 mL three-necked round bottom flask. 15 g (28 mmol) was added, 15.65 g (61 mmol) of bis(pinacolato)dibrone was added, and 190 mL of 1,4-dioxane was added. Thereafter, 0.46 g (0.5 mmol) of 1,1'bis[(diphenylphosphino)ferrocene]dichloropalladium(II)chloromethane complex was added, 5.5 g (56 mmol) of potassium acetate was added, and heating was stirred while refluxing. . After reacting for 12 hours, the reactant was cooled to room temperature, and extracted with distilled water and ethyl acetate. Then, after drying with anhydrous magnesium sulfate, it was concentrated under reduced pressure. After concentration, the obtained residue was separated with a silica gel column (hexane : ethyl acetate = 20:1) to give 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 thereto. Then, 25 g (93.3 mmol) of 1-(3-bromopropoxy)-4-vinylbenzene was added, 38.7 g (280 mmol) of potassium carbonate and 7.75 g (47 mmol) of potassium iodide were added, respectively. It was heated and reacted for 30 hours.

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

6. Preparation of compounds 1-7

Compounds 1-6 obtained above were placed in a 1,000 mL three-necked round bottom flask. 10g (17 mmol), compound 1-5, 21.7 g (37.4 mmol) were added, and 200 mL of 1,4-dioxane was added. Thereafter, 0.98 g (0.8 mmol) of tetrakis(triphenylphosphine)palladium(0) was added, and 150 mL of a 2 M potassium carbonate aqueous solution was added, followed by heating and stirring at 80°C for 16 hours.

After cooling the reactant to room temperature, it was extracted with distilled water and methylene chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. After concentration, the obtained residue was separated with 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 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).

manufacturing example 2. Preparation of organic light-emitting compounds 2

Organic light emitting compounds represented by Chemical Formulas 1-9 were prepared through Reaction Scheme 4 below. At this time, 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, 10 g (17 mmol) and Compound 1-5, 9.9 g (17 mmol) were put in a 1,000 mL three-necked round bottom flask, and 200 mL of 1,4-dioxane was added thereto. Thereafter, 0.98 g (0.8 mmol) of tetrakis(triphenylphosphine)palladium(0) was added, and 150 mL of 1 M potassium carbonate aqueous solution was added, followed by heating and stirring at 80° C. for 12 hours.

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

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- After adding 2.01 g (5.5 mmol) of 2-nyl)-9H-carbazole, 200 mL of 1,4-dioxane was added. Thereafter, 0.3 g (0.3 mmol) of tetrakis(triphenylphosphine)palladium(0) was added thereto, and 100 mL of a 2 M potassium carbonate aqueous solution was added thereto, followed by heating and stirring at 80°C for 12 hours.

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

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

^1H 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. Manufacturing of organic light emitting devices

A glass substrate with a size of 25 mm x 25 mm x 0.7 mm having ITO (Indium Tin Oxide) transparent electrode lines with a thin film thickness of 150 nm was ultrasonically cleaned in distilled water in which detergent was dissolved for 20 minutes, followed by isopropyl alcohol for 10 minutes. while washing once. After the isopropyl alcohol cleaning was completed, the substrate was ultrasonically cleaned twice for 10 minutes using distilled water and dried. Subsequently, oxygen/nitrogen plasma was treated for 2 minutes in a vacuum deposition equipment.

After the plasma work of the substrate is finished, the substrate is vacuum adsorbed on the spin coater equipment to manufacture a device for solution process, and then PEDOT:PSS, a polythiophene derivative, is used 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.

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

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

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

Example 2. Manufacturing 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

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 (25 mm X 25 mm X 0.7 mm) was ultrasonically cleaned in distilled water containing detergent for 10 minutes, and then washed twice for 10 minutes with distilled water. After the distilled water cleaning was completed, the substrate was sequentially ultrasonically washed for 10 minutes using solvents such as isopropyl alcohol, acetone, and methanol, and then dried.

A liquid composition was prepared by dissolving the organic light emitting compound prepared in Preparation Examples 1 and 2 in toluene at 1% by weight, respectively. Each liquid composition prepared above was applied on a glass substrate mounted on a spin coater, and a first thin film was formed at 500 rpm for 15 seconds, and then a second thin film was formed at 1,000 rpm for 30 seconds. Subsequently, the film on the glass substrate was baked at 160 DEG C for 35 minutes each using a hot plate in a nitrogen-purged glove box, and then the film on the glass substrate was cooled to room temperature. The glass substrate on which the film was formed was dipped in isopropyl alcohol, toluene, and chlorobenzene, respectively, and then the solvent resistance of the thin film was measured by 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 excellent solvent resistance.

Experimental Example 2. Evaluation of electroluminescent properties

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

[Table 2]

As shown in Table 2, it can be confirmed that the organic light emitting device manufactured according to the embodiment of the present invention has excellent light emitting characteristics in terms of current efficiency and power efficiency by including the organic light emitting compound prepared according to the manufacturing example in the light emitting layer. could

In the 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 embodiments. Therefore, various modifications or equivalent ranges of embodiments may exist within the scope of the technical idea 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 range should be construed as belonging to the scope of the present invention.

Claims (7)

An organic light-emitting compound represented by Formula 1 or Formula 2 below:
[Formula 1]

(In Formula 1 above,
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 a straight or branched C1-C20 alkylene or a straight or branched C2-C20 alkenylene;
R5 and R6 are each independently linear or branched C1-C20 alkyl, straight or branched C2-C20 alkenyl, C3-C20 cycloalkyl or C6-C30 aryl.)

[Formula 2]

(In Formula 2 above,
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 a straight or branched C1-C20 alkylene or a straight or branched C2-C20 alkenylene.)
According to claim 1,
In Formula 1, R1 and R2 are each independently a straight-chain or branched-chain C1-C20 alkyl or a straight-chain or branched-chain C2-C20 alkenyl;
R3 and R4 are each independently linear or branched C1-C20 alkylene;
R5 and R6 are each independently a straight or branched C1-C20 alkyl or a straight or branched C2-C20 alkenyl;
In Formula 2, R1 and R2 are each independently a straight-chain or branched-chain C1-C20 alkyl or a straight-chain or branched-chain C2-C20 alkenyl;
R3 and R4 are each independently a straight-chain or branched-chain C1-C20 alkylene organic light-emitting compound.
According to 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 alkylene;
R5 and R6 are each independently a straight-chain or branched-chain 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 straight-chain or branched-chain C1-C10 alkylene organic light-emitting compound.
According to 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 alkylene;
R5 and R6 are each independently a straight-chain or branched-chain 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 alkylene organic light emitting compound.
According to claim 1,
In Formula 1, R1 and R2 are straight-chain C5 alkenyl,
R3 and R4 are straight-chain C3 alkylene;
R5 and R6 are straight-chain straight-chain C5 alkenyl;
In Formula 2, R1 and R2 are straight-chain C5 alkenyl,
R3 and R4 are linear C3 alkylene organic light-emitting compounds.
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,
Method for producing an organic light emitting compound represented by Formula 2 is prepared through the following Reaction Scheme 2:
[Scheme 1]

(In Scheme 1 above,
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 a straight or branched C1-C20 alkylene or a straight or branched C2-C20 alkenylene;
X is a halogen element.)

[Scheme 2]

(In Scheme 2 above,
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 a straight or branched C1-C20 alkylene or a straight or branched C2-C20 alkenylene;
X is a halogen element.)

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