KR102169273B1 - Organic electroluminescent compound comprising acridine derivative and organic electroluminescent device comprising same - Google Patents

Abstract

The organic light-emitting compound of the present invention, including an acridine derivative, controls the charge balance in the organic material layer through an appropriate combination of an acridine derivative and a cyclic compound, so that luminance, power efficiency, heat resistance, charge transport performance and charge injection performance Because it is excellent in color purity and luminous efficiency, it is used as a light-emitting material of an organic light-emitting device, showing low driving voltage, high luminous luminance and luminous efficiency to the organic light-emitting device, and thus, maximizing performance and lifespan in a full-color organic panel. Can provide an improvement.

Description

An organic light-emitting compound containing an acridine derivative and an organic light-emitting device containing the same {ORGANIC ELECTROLUMINESCENT COMPOUND COMPRISING ACRIDINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING SAME}

The present invention relates to an organic light-emitting compound comprising an acridine derivative and an organic light-emitting device comprising the same.

Recently, organic light emitting devices capable of low voltage driving by self-luminous type have superior viewing angles and contrast ratios compared to liquid crystal displays (LCDs), which are the mainstream of flat panel display devices, and are lightweight and thin because they do not need a backlight. It is advantageous in terms of power consumption and has a wide color reproduction range, attracting attention as a next-generation display device.

In general, an organic light emitting device has a structure including a cathode (electron injection electrode) and an anode (hole injection electrode), and an organic material layer between the two electrodes. At this time, the organic material layer is a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron injection layer (EIL) in addition to the light emitting layer (EML). , an electron injection layer), and may further include an electron blocking layer (EBL) or a hole blocking layer (HBL) due to the emission characteristics of the emission layer.

When an electric field is applied to the organic light-emitting device of this structure, holes are injected from the anode and electrons are injected from the cathode, and holes and electrons are recombined in the emission layer through the hole transport layer and the electron transport layer, respectively, and the emission excitons (excitons , exitons). The formed luminescent excitons emit light while transitioning to ground states.

The light-emitting material can be classified into blue, green, and red light-emitting materials, and yellow and orange light-emitting materials necessary for realizing a better natural color according to the light-emitting color. In addition, in order to increase the efficiency and stability of the light-emitting state, a light-emitting dye (dopant) is also doped into the light-emitting layer (host). The principle is that when a small amount of a dopant having an energy band gap smaller than that of a host that mainly constitutes the light emitting layer is mixed with the light emitting layer, excitons generated from the host are transported as a dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

Until now, various compounds have been known as light-emitting materials used in the light-emitting layer of an organic light-emitting device. However, in the case of an organic light-emitting device using a light-emitting material known so far, there have been many difficulties in practical use due to high driving voltage, low efficiency, and short lifespan. Accordingly, efforts have been made to develop low voltage driving, high luminance, and long-life organic light-emitting devices using materials having excellent light-emitting characteristics.

In order to solve the above problems, an object of the present invention is to provide a novel organic light emitting compound having improved color purity, luminous efficiency, luminance, power efficiency, and heat resistance.

Another object of the present invention is to provide an organic light-emitting device including the compound, which exhibits a low driving voltage, high luminous efficiency and luminance, and is capable of realizing a long life.

In order to achieve the above object, the present invention provides an organic light-emitting compound comprising an acridine derivative represented by the following Formula 1:

[Formula 1]

In the above formula,

X is a substituted or unsubstituted C, O, P, S, Se or Si, and when X is O, the nitrogen atom of acridine cannot be bonded to the 3rd position of the heteroaryl-based moiety;

R ₁ to R ₁₇ are each independently hydrogen; heavy hydrogen; C _1-30 alkyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _2-30 alkenyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _2-30 alkynyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _1-30 alkoxy group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _6-30 aryloxy group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _6-36 aryl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; Or C _2-36 heteroaryl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group, and optionally, adjacent groups of R ₁ to R ₁₇ are bonded to each other to form a saturated or unsaturated carbon ring. I can.

In addition, it provides a method for preparing Formula 1 comprising the step of reacting Formula 1-1 with Formula 1-2:

[Formula 1-1]

[Formula 1-2]

In the above, X and R ₁ to R ₁₇ are as defined in Formula 1.

In addition, the present invention provides an organic light-emitting device including the compound represented by Formula 1 as a light-emitting material in an organic material layer.

The organic light-emitting compound of the present invention is excellent in brightness, power efficiency, heat resistance, charge transport performance and charge injection performance by controlling the charge balance in the organic material layer through appropriate harmony of the acridine derivative and the cyclic compound. Since can be increased, it can be applied to one or more of the functional layer material of the organic light emitting device and the host or dopant of the light emitting layer. Accordingly, the organic light-emitting device including the compound of the present invention exhibits a low driving voltage, high luminance and luminous efficiency, thereby maximizing performance and improving lifespan in a full-color organic panel.

1 schematically shows a cross-section of an OLED according to an embodiment of the present invention,
2 shows a band diagram of an organic light emitting diode having a light emitting principle by an organic light emitting phenomenon.
The symbol of the drawing
10: substrate
11: anode
12: hole injection layer
13: hole transport layer
14: light emitting layer
15: electron transport layer
16: cathode

The compound of the present invention represented by the following Formula 1 is characterized in that an acridine-based moiety and an aryl-based or heteroaryl-based moiety are directly connected to the nitrogen atom of acridine:

<Formula 1>

In the above formula,

X is a substituted or unsubstituted C, O, P, S, Se or Si, and when X is O, the nitrogen atom of acridine cannot be bonded to the 3rd position of the heteroaryl-based moiety;

R ₁ to R ₁₇ are each independently hydrogen; heavy hydrogen; C _1-30 alkyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _2-30 alkenyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _2-30 alkynyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _1-30 alkoxy group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _6-30 aryloxy group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _6-36 aryl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; Or C _2-36 heteroaryl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group, and optionally, adjacent groups of R ₁ to R ₁₇ are bonded to each other to form a saturated or unsaturated carbon ring. I can.

When each of R ₁ to R ₁₀ is substituted with deuterium, it may be deuterated to at least 20%, preferably at least 40%, more preferably at least 50% of R ₁ to R ₁₀ .

In addition, when the aryl-based or heteroaryl-based moiety directly connected to the nitrogen atom of the acridine-based moiety in the compound is substituted with deuterium, it is preferably deuterated by at least 50%.

In addition, the substituents of X and R ₁ to R ₁₇ are each independently deuterium, halogen, nitrile group, nitro group, C _1-30 alkyl group, C _1-30 alkoxy group, C _3-30 cycloalkyl group, C _3-30 heterocycloalkyl group, C _6-30 aryl group, C _5-30 heteroaryl group, C _1-30 alkyloxy group, C _6-30 aryloxy group and C _6-30 arylamine It is preferable to be substituted with one or more substituents selected from the group consisting of groups, but is not limited thereto, and adjacent groups may be bonded to each other to form a saturated or unsaturated carbon ring.

In the present invention, preferred examples of the compound represented by Formula 1 are as follows:

In the compound of Formula 1 according to the present invention, an acridine-based moiety and an aryl-based or heteroaryl-based moiety are directly connected to the nitrogen atom of acridine, so that the acridine derivative and the cyclic compound are properly combined in the organic material layer. Controls charge balance. Due to this, it is possible to increase color purity and luminous efficiency due to excellent luminance, power efficiency, heat resistance, charge transport performance and charge injection performance, so it can be applied to one or more of the functional layer material of the organic light emitting device and the host or dopant of the light emitting layer. have.

Therefore, when the compound of the present invention is applied to an organic light emitting device, characteristics such as driving voltage and light emission efficiency of the light emitting device can be improved.

In addition, the present invention provides a method for preparing Formula 1 comprising the step of reacting Formula 1-1 and Formula 1-2 below:

[Formula 1-1]

[Formula 1-2]

In the above, X and R ₁ to R ₁₇ are as defined in Formula 1.

As a specific example, the compound of Formula 1 according to the present invention may be prepared according to the method according to Scheme 1 below.

[Scheme 1]

In Reaction Scheme 1, X is as defined in Formula 1, and each R corresponds to R ₁ and R ₂ in Formula 1-1, respectively.

In addition, the present invention provides an organic light emitting device including the compound represented by Formula 1 as a light emitting material in an organic material layer. At this time, the compound of the present invention may be used alone or together with a known organic light emitting compound.

In addition, the organic light-emitting device of the present invention includes one or more organic material layers including the compound represented by Chemical Formula 1, and a method of manufacturing the organic light-emitting device will be described below.

The organic light emitting device includes an organic material layer such as a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL) between an anode and a cathode. It can contain more than one.

First, an anode is formed by depositing a material for an anode electrode having a high work function on the substrate. At this time, the substrate may be a substrate used in a conventional organic light emitting device, in particular, it is preferable to use a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance. In addition, as a material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, may be used. The material for the anode electrode may be deposited by a conventional anode forming method, and specifically, may be deposited by a vapor deposition method or a sputtering method.

Then, the material of the hole injection layer on the anode electrode can be formed by a method such as a vacuum deposition method, a spin coating method, a cast method, or a LB (Langmuir-Blodgett) method, but it is easy to obtain a uniform film quality, and It is preferable to form by a vacuum evaporation method from the viewpoint of being difficult to generate. When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal characteristics of the target hole injection layer, etc., but in general, a deposition temperature of 50-500 ℃, It is preferable to appropriately select a vacuum degree of 10 ^-8 to 10 ^-3 torr, a deposition rate of 0.01 to 100 Å/sec, and a layer thickness of 10 Å to 5 µm.

The hole injection layer material is not particularly limited, and TCTA(4,4',4"-tri(N-carbazolyl) tree, which is a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or a starburst-type amine derivative Phenylamine), m-MTDATA(4,4',4"-tris(3-methylphenylamino)triphenylamine), m-MTDAPB(4,4',4"-tris(3-methylphenylamino)phenoxybenzene ), HI-406(N ¹ ,N ¹ '-(biphenyl-4,4'-diyl) bis(N ¹ -(naphthalen- ¹ -yl)-N ⁴ ,N ⁴ -diphenylbenzene-1,4 -Diamine) or the like can be used as a material for the hole injection layer.

Next, the material of the hole transport layer on the hole injection layer can be formed by a method such as vacuum deposition, spin coating, casting, LB method, etc., but it is easy to obtain a uniform film quality and is difficult to generate pin holes. It is preferably formed by a vapor deposition method. When the hole transport layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound to be used, but in general, it is preferable to select within the same range of conditions as the hole injection layer formation.

In addition, the material for the hole transport layer is not particularly limited, and may be arbitrarily selected from conventional known materials used for the hole transport layer. Specifically, the material for the hole transport layer is a carbazole derivative such as N-phenylcarbazole and polyvinylcarbazole, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-ratio Phenyl]-4,4'-diamine (TPD), N.N'-di(naphthalen-1-yl)-N,N'-diphenyl benzidine (α-NPD), etc. Derivatives and the like can be used.

Thereafter, the light emitting layer material can be formed on the hole transport layer by a method such as vacuum deposition, spin coating, casting, LB method, etc., but it is easy to obtain a uniform film quality and is difficult to generate pin holes. It is preferable to form by. When the light emitting layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound to be used, but in general, it is preferable to select it within the same range of conditions as the hole injection layer formation. In addition, the light-emitting layer material may use the compound represented by Formula 1 of the present invention as a host or dopant.

When the compound represented by Formula 1 is used as a light emitting host, a phosphorescent or fluorescent dopant may be used together to form a light emitting layer. At this time, as the fluorescent dopant, IDE102 or IDE105 available from Idemitsu, or BD142 (N ⁶ ,N ¹² -bis(3,4-dimethylphenyl)-N ⁶ ,N ¹² -dimethylcrysen- 6,12-diamine) can be used, and as the phosphorescent dopant, the green phosphorescent dopant Ir(ppy) ₃ (tris(2-phenylpyridine) iridium), the blue phosphorescent dopant F2Irpic (iridium(III) bis[4,6- Difluorophenyl)-pyridinato-N,C2'] picolinate), UDC's red phosphorescent dopant RD61, etc. may be co-vacuum deposited (doped). The doping concentration of the dopant is not particularly limited, but it is preferable that the dopant is doped at 0.01 to 15 parts by weight relative to 100 parts by weight of the host. If the content of the dopant is less than 0.01 parts by weight, there is a problem in that the dopant amount is insufficient and color development is not performed properly. If the content of the dopant is more than 15 parts by weight, there is a problem that the efficiency is rapidly reduced due to concentration quenching.

In addition, in the case of using with a phosphorescent dopant in the light emitting layer, it is preferable to additionally laminate a hole inhibiting material (HBL) by vacuum deposition or spin coating in order to prevent diffusion of triplet excitons or holes into the electron transport layer. The hole-suppressing material that can be used at this time is not particularly limited, but any of the known materials used as hole-suppressing materials may be selected and used. For example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, or hole inhibiting materials described in Japanese Unexamined Patent Application Publication No. Hei 11-329734(A1), and the like, and representatively Balq (bis(8-hydride) Roxy-2-methylquinolinolnato)-aluminum biphenoxide), phenanthrolines-based compounds (eg, UDC's BCP (basocuproin)) and the like can be used.

An electron transport layer is formed on the light emitting layer formed as described above, wherein the electron transport layer is formed by a method such as a vacuum deposition method, a spin coating method, or a cast method, and is particularly preferably formed by a vacuum deposition method.

The electron transport layer material has a function of stably transporting electrons injected from the electron injection electrode, and its kind is not particularly limited, and, for example, a quinoline derivative, especially tris(8-quinolinolato)aluminum (Alq ₃ ), or ET4 (6,6'-(3,4-dimethyl-1,1-dimethyl-1H-silol-2,5-diyl)di-2,2'-bipyridine) can be used. In addition, an electron injection layer (EIL), which is a material that facilitates injection of electrons from the cathode, may be stacked on the electron transport layer, and the electron injection layer materials include LiF, NaCl, CsF, Li ₂ O, BaO, etc. The material of can be used.

In addition, the deposition conditions of the electron transport layer vary depending on the compound to be used, but it is generally preferable to select the electron transport layer within the same range of conditions as the formation of the hole injection layer.

Thereafter, an electron injection layer material may be formed on the electron transport layer, wherein the electron transport layer is formed by a vacuum deposition method, a spin coating method, a cast method, etc., and in particular, a vacuum deposition method. It is preferably formed by.

Finally, a metal for forming a cathode is formed on the electron injection layer by a method such as vacuum deposition or sputtering, and is used as a cathode. Here, as the metal for forming the cathode, a metal having a low work function, an alloy, an electroconductive compound, and a mixture thereof may be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. There is this. In addition, a transmissive cathode using ITO or IZO may be used to obtain a top light emitting device.

The organic light-emitting device of the present invention can have an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an organic light-emitting device having a cathode structure, as well as an organic light-emitting device having a variety of structures. It is also possible to further form a layer or an intermediate layer of two layers.

As described above, the thickness of each organic material layer formed according to the present invention can be adjusted according to the required degree, preferably 10 to 1,000 nm, more preferably 20 to 150 nm.

In addition, in the present invention, the organic material layer including the compound represented by Chemical Formula 1 has an advantage of having a uniform surface and excellent shape stability because the thickness of the organic material layer can be controlled on a molecular basis.

The organic light-emitting compound of the present invention has excellent luminance, power efficiency, heat resistance, charge transport performance and charge injection performance to increase color purity and luminous efficiency, so it is used as a light-emitting material of an organic light-emitting device and has a low driving voltage for the organic light-emitting device. And high luminous luminance and luminous efficiency, thereby maximizing performance and improving lifespan in a full-color organic panel.

Hereinafter, preferred examples are presented to aid in the understanding of the present invention, but the following examples are only illustrative of the present invention, and the scope of the present invention is not limited to the following examples.

[Example 1: Synthesis of Compound 1]

9,9-dimethyl-9,10-dihydroacridine 5 g, 4-bromodibenzo[b,d]furan 7.1 g, t-BuONa 3.5 g, Pd ₂ (dba) ₃ 0.9 g, (t-Bu) ₃ P 1.2 ml Was dissolved in 100 ml of toluene and stirred under reflux. When the reaction was completed, the mixture was extracted with distilled water and EA, followed by column purification to obtain compound 1. (61% yield)

m/z: 375.16 (100.0%), 376.17 (29.5%), 377.17 (4.4%)

[Example 2: Synthesis of Compound 2]

After dissolving 10 g of 2-bromo-N-phenylaniline in 100 ml of THF, the reaction temperature was lowered to -78 °C, and 20 ml of BuLi 2.5 M was slowly added dropwise and stirred for 1 hour. After 11 g of benzophenone was dissolved in 100 ml of THF, slowly added dropwise, the temperature was raised to room temperature, and the mixture was stirred for 12 hours. After the reaction was completed, the mixture was extracted with distilled water and MC, water was removed with anhydrous magnesium sulfate, and the solid obtained by filtration under reduced pressure was dissolved in 100 ml of Acetic acid without further purification, and then 7 ml of sulfuric acid was added dropwise and stirred under reflux. After the reaction was completed, extraction was performed with distilled water and MC, and the resulting solid was purified by column to obtain 7.1 g of I ₂ . (Yield 53%)

After dissolving 7 g of I ₂ , 6.5 g of 4-bromodibenzo[b,d]furan, 3 g of t-BuONa, 0.7 g of Pd ₂ (dba) ₃ , 1 ml of (t-Bu) ₃ P in 150 ml of toluene, Stir at reflux. When the reaction was completed, the mixture was extracted with distilled water and EA and purified by column to obtain a compound. (Yield 67%)

m/z: 499.19 (100.0%), 500.20 (40.3%), 501.20 (8.1%), 502.20 (1.1%)

[Example 3: Synthesis of Compound 3]

Except for reacting benzophenone with 9H-fluoren-9-one, the following compound 3 was obtained by the same method as the synthesis method of compound 2.

m/z: 497.18 (100.0%), 498.18 (40.3%), 499.18 (8.1%), 500.19 (1.1%)

[Example 4: Synthesis of Compound 4]

Except for reacting Benzophenone with di(pyridin-3-yl)methanone, the following compound 4 was obtained in the same manner as in the synthesis method of compound 2.

m/z: 501.18 (100.0%), 502.19 (38.2%), 503.19 (7.3%), 502.18 (1.1%)

[Example 5: Synthesis of Compound 5]

Except for reacting bromodibenzo[b,d]furan (247.09) and 4-bromodibenzo[b,d]furan with 1-bromodibenzo[b,d]furan, the following compound 5 was prepared in the same manner as the synthesis method of compound 1. Got it.

m/z: 375.16 (100.0%), 376.17 (29.5%), 377.17 (4.4%)

[Example 6: Synthesis of Compound 6]

Except for reacting 4-bromodibenzo[b,d]furan with 1-bromodibenzo[b,d]furan, the following compound 6 was obtained in the same manner as the synthesis method of compound 2.

m/z: 499.19 (100.0%), 500.20 (40.3%), 501.20 (8.1%), 502.20 (1.1%)

[Example 7: Synthesis of Compound 7]

Except for reacting 4-4-bromodibenzo[b,d]furan with 1-bromodibenzo[b,d]furan, the following compound 7 was obtained in the same manner as the synthesis method of compound 3.

m/z: 497.18 (100.0%), 498.18 (40.3%), 499.18 (8.1%), 500.19 (1.1%)

[Example 8: Synthesis of Compound 8]

Except for reacting 4-4-bromodibenzo[b,d]furan with 1-bromodibenzo[b,d]furan, the following compound 8 was obtained in the same manner as the synthesis method of compound 4.

m/z: 501.18 (100.0%), 502.19 (38.2%), 503.19 (7.3%), 502.18 (1.1%)

[Example 9: Synthesis of Compound 9]

After dissolving 10 g of 2-bromo-N-phenylaniline in 100 ml of THF, the reaction temperature was lowered to -78 °C, and 20 ml of BuLi 2.5 M was slowly added dropwise and stirred for 1 hour. After dissolving 15.2 g of bis(4-chlorophenyl)methanone in 150 ml of THF, slowly added dropwise, the temperature was raised to room temperature, and the mixture was stirred for 12 hours. After the reaction was completed, the mixture was extracted with distilled water and MC, water was removed with anhydrous magnesium sulfate, and the solid obtained by filtration under reduced pressure was dissolved in 150 ml of Acetic acid without further purification, and 10 ml of sulfuric acid was added dropwise and stirred under reflux. After the reaction was completed, extraction was performed with distilled water and MC, and the resulting solid was purified by column to obtain 10 g of I ₃ . (Yield 62%)

In the above step I ₃ 9 g, 4-bromodibenzo[b,d]furan 6.65 g, t-BuONa 3.2 g, Pd ₂ (dba) ₃ 0.8 g, (t-Bu) ₃ P 1.1 ml dissolved in 200 ml of toluene Then, the mixture was stirred under reflux. When the reaction was completed, extraction was performed with distilled water and EA, followed by column purification to obtain 11 g of I _3-1 . (Yield 59%)

I _3-1 of the above step 10 g, diphenylamine 6.85 g, t-BuONa 2.5 g, Pd ₂ (dba) ₃ 0.6 g, (t-Bu) ₃ P 1.6 ml was dissolved in 200 ml of toluene and stirred under reflux. When the reaction was completed, the mixture was extracted with distilled water and EA and purified by column to obtain 8 g of Compound 9. (Yield 55%)

m/z: 833.34 (100.0%), 834.34 (67.1%), 835.35 (21.8%), 836.35 (4.8%)

[Example 10: Synthesis of Compound 10]

Except that diphenylamine was reacted with 9H-carbazole, the following compound 10 was obtained by the same method as the synthesis method of compound 9.

m/z: 829.31 (100.0%), 830.31 (67.1%), 831.32 (21.7%), 832.32 (4.8%)

[Example 11: Synthesis of Compound 11]

Compound 11 was obtained in the same manner as in the synthesis method of compound 9, except that bis(4-chlorophenyl)methanone was reacted with 2,7-dichloro-9H-fluoren-9-one.

m/z: 831.32 (100.0%), 832.33 (66.5%), 833.33 (22.7%), 834.34 (4.7%), 832.32 (1.1%)

[Example 12: Synthesis of Compound 12]

Except for reacting 4-4-bromodibenzo[b,d]furan with 1-bromodibenzo[b,d]furan, the following compound 12 was obtained in the same manner as in the synthesis method of compound 9.

m/z: 833.34 (100.0%), 834.34 (67.1%), 835.35 (21.8%), 836.35 (4.8%)

[Example 13: Synthesis of Compound 13]

Except that diphenylamine was reacted with 9H-carbazole, the following compound 13 was obtained in the same manner as the synthesis method of compound 12.

m/z: 829.31 (100.0%), 830.31 (67.1%), 831.32 (21.7%), 832.32 (4.8%)

[Example 14: Synthesis of Compound 14]

Except for reacting 4-4-bromodibenzo[b,d]furan with 1-bromodibenzo[b,d]furan, the following compound 14 was obtained in the same manner as in the synthesis method of compound 11.

m/z: 831.32 (100.0%), 832.33 (66.5%), 833.33 (22.7%), 834.34 (4.7%), 832.32 (1.1%)

[Example 15: Synthesis of Compound 15]

9,9-dimethyl-9,10-dihydroacridine 5 g, 4-bromodibenzo[b,d]thiophene 6.9 g, t-BuONa 3.5 g, Pd ₂ (dba) ₃ 0.9 g, (t-Bu) ₃ P 1.2 ml Was dissolved in 100 ml of toluene and stirred under reflux. When the reaction was completed, the mixture was extracted with distilled water and EA, followed by column purification to obtain compound 15. (61% yield)

m/z: 391.14 (100.0%), 392.14 (30.4%), 393.14 (4.9%), 393.15 (4.2%), 394.14 (1.3%)

[Example 16: Synthesis of Compound 16]

Except for reacting 4-4-bromodibenzo[b,d]furan with 4-bromodibenzo[b,d]thiophene, the following compound 16 was obtained in the same manner as in the synthesis method of compound 2.

m/z: 515.17 (100.0%), 516.17 (41.2%), 517.18 (7.9%), 517.17 (5.0%), 518.17 (1.9%), 518.18

[Example 17: Synthesis of Compound 17]

Except for reacting 4-4-bromodibenzo[b,d]furan with 4-bromodibenzo[b,d]thiophene, the following compound 17 was obtained in the same manner as in the synthesis method of compound 3.

m/z: 513.16 (100.0%), 514.16 (40.3%), 515.16 (8.4%), 515.15 (4.5%), 516.15 (1.8%), 514.15 (1.2%), 516.17 (1.0%)

[Example 18: Synthesis of Compound 18]

Except for reacting 4-4-bromodibenzo[b,d]furan with 2-bromo-9,9-dimethyl-9H-fluorene, the following compound 18 was obtained in the same manner as the synthesis method of compound 4.

[Example 19: Synthesis of Compound 19]

Except for reacting 4-4-bromodibenzo[b,d]furan with 2-bromo-9,9-dimethyl-9H-fluorene, the following compound 19 was obtained in the same manner as the synthesis method of compound 2.

m/z: 525.25 (100.0%), 526.25 (43.6%), 527.25 (9.3%), 528.26 (1.3%)

[Example 20: Synthesis of Compound 20]

Except for reacting 4-4-bromodibenzo[b,d]furan with 2-bromo-9,9-dimethyl-9H-fluorene, the following compound 20 was obtained in the same manner as the synthesis method of compound 4.

Fabrication of organic light emitting device using host

An organic light-emitting device was manufactured with the structure shown in FIG. 1. Specifically, a glass substrate coated with a 1500 Å thick thin film of indium tin oxide (ITO) was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonically clean with a solvent such as isopropyl alcohol, acetone, methanol, etc., dry, transfer to a plasma cleaner, and clean the substrate for 5 minutes using oxygen plasma, and then use a thermal vacuum evaporator on the top of the ITO substrate. evaporator) to form 2-TNATA 600 Å as a hole injection layer and NPB 200 Å as a hole transport layer.

Next, the host materials of Examples 1 to 20 synthesized in the above example were doped with 7% Ir (ppy) ₃ to form a 300 Å film. Next, 300 Å of TPBi was formed as an electron transport layer, 10 Å of LiF and 1000 Å of aluminum (Al) were formed, and the device was encapsulated in a glove box to fabricate an organic light-emitting device.

Hole transport layer Fabrication of used organic light emitting device

The glass substrate coated with indium tin oxide (ITO) having a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonically clean with a solvent such as isopropyl alcohol, acetone, methanol, etc., dry, transfer to a plasma cleaner, and clean the substrate for 5 minutes using oxygen plasma, and then use a thermal vacuum evaporator on the top of the ITO substrate. evaporator) was used as a hole injection layer to form a 2-TNATA 600 Å and a hole transport layer to form 200 Å of the compound synthesized in Examples 1 to 20. Next, mCP was doped with 7% Ir(ppy) ₃ to form a 300 Å film. Next, TPBi 300 Å was formed as an electron transport layer, LiF 10 Å and aluminum (Al) 1000 Å were formed, and the device was encapsulated in a glove box to manufacture an organic light-emitting device.

Comparative Example: Fabrication of an organic light emitting device using a hole transport layer

An organic light-emitting device was fabricated in the same manner, except that NPB and mCP were used as the hole transport layer and the emission layer host of the above example.

Performance evaluation of organic light emitting device

A voltage is applied to the Keithley 2400 source measurement unit to inject electrons and holes, and the luminance when light is emitted is measured using a Konica Minolta spectroradiometer (CS-2000). By doing so, the performance of the organic light emitting device of Examples and Comparative Examples was evaluated by measuring the current density and luminance with respect to the applied voltage under atmospheric pressure conditions, and the results are shown in Table 1.

Device composition 1000nit LE(cd/A) EQE(%) PE(lm/w) Example 21 ITO / 2-TNATA / NPB /
Compound 1: Ir(ppy)3(7%) / TPBi / LiF / Al 38.5 17.7 18 Example 22 ITO / 2-TNATA / NPB /
Compound 2: Ir(ppy)3(7%) / TPBi / LiF / Al 39.2 17.9 18.3 Example 23 ITO / 2-TNATA / NPB /
Compound 3: Ir(ppy)3(7%) / TPBi / LiF / Al 40 19 19.2 Example 24 ITO / 2-TNATA / NPB /
Compound 4: Ir(ppy)3(7%) / TPBi / LiF / Al 41 19.3 20 Example 25 ITO / 2-TNATA / NPB /
Compound 5: Ir(ppy)3(7%) / TPBi / LiF / Al 38.2 17.8 16.9 Example 26 ITO / 2-TNATA / NPB /
Compound 6: Ir(ppy)3(7%) / TPBi / LiF / Al 39.1 18 17.9 Example 27 ITO / 2-TNATA / NPB /
Compound 7: Ir(ppy)3(7%) / TPBi / LiF / Al 39.3 18.2 17.5 Example 28 ITO / 2-TNATA / NPB /
Compound 8: Ir(ppy)3(7%) / TPBi / LiF / Al 40.9 18.9 19 Example 29 ITO / 2-TNATA / NPB /
Compound 10: Ir(ppy)3(7%) / TPBi / LiF / Al 41.1 19.5 20.2 Example 30 ITO / 2-TNATA / compound 9 /
mCP:Ir(ppy)3(7%) / TPBi / LiF / Al 39.9 19.1 18.7 Example 31 ITO / 2-TNATA / compound 10 /
mCP:Ir(ppy)3(7%) / TPBi / LiF / Al 40.6 18.8 19.5 Example 32 ITO / 2-TNATA / compound 11 /
mCP:Ir(ppy)3(7%) / TPBi / LiF / Al 40.9 18.9 19.8 Comparative example ITO / 2-TNATA / NPB /
mCP:Ir(ppy)3(7%) / TPBi / LiF / Al 38 16.6 15.2

As shown in Table 1, it can be seen that the organic light emitting devices of Examples 21 to 32 using the compounds synthesized in Examples 1 to 11 according to the present invention have superior luminance, efficiency, and current density compared to the comparative example.

Claims (11)

An organic light-emitting compound comprising an acridine derivative represented by the following formula (1):
[Formula 1]

In the above formula,
X is a substituted or unsubstituted O, P, S, Se or Si, and when X is O, the nitrogen atom of acridine cannot be bonded to the 3rd position of the heteroaryl-based moiety;
R ₁ and R ₂ are each independently hydrogen; heavy hydrogen; C _1-30 alkyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _2-30 alkenyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _2-30 alkynyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _1-30 alkoxy group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _6-30 aryloxy group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _6-36 aryl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; Or a substituted or unsubstituted C _2-36 heteroaryl group substituted with deuterium, halogen, amino group, nitrile group, nitro group, and R ₁ and R ₂ may be bonded to each other to form a saturated or unsaturated carbon ring,
R ₃ to R ₁₇ are each independently hydrogen; heavy hydrogen; C _1-30 alkyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _2-30 alkenyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _2-30 alkynyl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _1-30 alkoxy group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; C _6-30 aryloxy group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, nitro group; It is a C _6-36 aryl group substituted or unsubstituted with deuterium, halogen, amino group, nitrile group, and nitro group. The method of claim 1,
When the compound of Formula 1 is substituted with deuterium, the organic light emitting compound is deuterated to at least 20%. The method of claim 1,
When the aryl-based or heteroaryl-based moiety directly connected to the nitrogen atom of the acridine-based moiety is substituted with deuterium, the organic light-emitting compound is at least 50% deuterated. An organic light emitting compound, characterized in that represented by any one of the following formulas:

delete delete An organic light-emitting device comprising an anode, a cathode, and one or more organic material layers containing the compound of claim 1 between two electrodes. The method of claim 7,
The organic light emitting device, wherein the organic material layer is at least one selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. The method of claim 8,
The organic light emitting device, characterized in that the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer each have a thickness of 10 to 1,000 nm. The method of claim 7,
An organic light-emitting device, wherein the organic material layer contains the compound of claim 1 as a light emitting host or a dopant. The method of claim 10,
An organic light-emitting device, characterized in that the dopant is added in an amount of 0.01 to 15 parts by weight based on 100 parts by weight of the host.

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