KR101847578B1 - Fused aromatic compounds and organic light-emitting diode including the same - Google Patents

Abstract

상기 식에서, R₁ 내지 R₃, L, m, n 및 o는 발명의 상세한 설명 또는 청구항에 정의된 바와 같다.The present invention relates to a condensed aromatic compound and an organic electroluminescent device including the condensed aromatic compound. More specifically, the present invention relates to a condensed aromatic compound represented by the following formulas (1-a) and (1-b) . According to the present invention, it is possible to provide an organic electroluminescent device having low-voltage driving and excellent brightness.
[Chemical Formula 1-a] [Chemical Formula 1-b]

Wherein R ₁ to R ₃ , L, m, n and o are as defined in the description or claims of the invention.

Description

[0001] The present invention relates to a condensed aromatic compound and an organic electroluminescent device including the condensed aromatic compound,

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a condensed aromatic compound and an organic electroluminescent device including the condensed aromatic compound. More particularly, the present invention relates to a condensed aromatic compound having excellent low-voltage driving and high luminance and an organic electroluminescent device including the condensed aromatic compound.

Recently, the demand for a flat display device with a small space occupation is increasing due to the enlargement of the display device. The liquid crystal display, which is a typical flat display device, has an advantage that it can be lighter than a conventional cathode ray tube (CRT) The viewing angle is limited and a back light is necessarily required. On the other hand, organic light emitting diodes (OLEDs), which are new flat display devices, are displays using a self-luminous phenomenon, which have a large viewing angle and can be thinner and thinner than a liquid crystal display, have.

Since the representative organic electroluminescent device was known by Gurnee in 1969 (US 3,172,862, US 3,173,050), its performance limitations have limited its use to various applications. However, in 1987, Eastman Kodak co (Applied Phys. Lett., 51, 913 (1987); J. Applied Phys., 65, 3610 (1989)). And has developed at a rapid pace. Currently, organic electroluminescent devices have excellent characteristics such as a low driving voltage (e.g., 10 V or less), a wide viewing angle, a high speed response, and a high contrast compared to a plasma display panel or an inorganic electroluminescent display, Can be used as a pixel, a pixel of a television image display or a surface light source, can be formed on a flexible transparent plastic substrate, can be made very thin and light, and has good color And is emerging as a suitable device for next generation flat panel display (FPD).

In this organic electroluminescent device, when electrons and holes are injected into the light emitting layer formed between the anode serving as the hole injecting electrode and the cathode serving as the electron injecting electrode, electrons and holes are coupled to form an excited exit, As a device that emits light by falling off, it is expected to be applied to a full color display in recent years.

Many studies have been made on an organic electroluminescent device employing anthracene or the like. However, until now, the characteristics such as luminance, driving stability and lifetime which are required until now have not been satisfactorily satisfied. Therefore, to be.

Accordingly, a first technical object of the present invention is to provide a condensed aromatic compound excellent in low-voltage driving and luminance.

A second object of the present invention is to provide an organic electroluminescent device comprising the condensed aromatic compound.

In order to accomplish the above object, the present invention provides a condensed aromatic compound represented by the following formulas (1-a) and (1-b).

[Chemical Formula 1-a] [Chemical Formula 1-b]

Wherein R ₁ to R ₃ are independently selected from the group consisting of hydrogen, deuterium, halogen, nitro, cyano, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 40 carbon atoms, A substituted or unsubstituted alkylsilyl group having 1 to 24 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 40 carbon atoms, m to o are an integer of 1 to 3, And m to o are greater than 2, plural R ₁ to R ₃ are each independently the same or different.

L is a divalent linking group which may be selected from the group consisting of a direct bond, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

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According to another embodiment of the present invention, it is preferable that R ₁ and R ₂ are a substituted or unsubstituted pyridine group, a substituted or unsubstituted quinoline group, or a substituted or unsubstituted carbazole group.

The condensed aromatic compound according to the present invention may be one of the compounds represented by the following formulas (2) to (85) described in the following examples.

According to another aspect of the present invention, there is provided a plasma display panel comprising: an anode; Cathode; And a layer containing a condensed aromatic derivative represented by the above formulas (1-a) and (1-b) between the anode and the cathode.

According to an embodiment of the present invention, the organic electroluminescent device may include a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer and an electron blocking layer between the anode and the cathode. Or more, and the condensed aromatic compound is preferably contained in the electron transporting layer between the anode and the cathode

When the condensed aromatic compound according to the present invention is used in an organic material layer of an organic electroluminescent device, the organic electroluminescent device is driven at a low voltage and the luminance is improved, which is very economical.

1 is a schematic view of an organic electroluminescent device according to an embodiment of the present invention.
2 is a representative view showing the structure of the condensed aromatic compound according to the present invention.

Hereinafter, the present invention will be described in more detail.

The condensed aromatic compound according to the present invention is selected from the compounds represented by the following formulas (1-a) and (1-b).

[Chemical Formula 1-a] [Chemical Formula 1-b]

Wherein R ₁ to R ₃ are independently selected from the group consisting of hydrogen, deuterium, halogen, nitro, cyano, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 40 carbon atoms, A substituted or unsubstituted alkylsilyl group having 1 to 24 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 40 carbon atoms, m to o are an integer of 1 to 3, And m to o are greater than 2, plural R ₁ to R ₃ are each independently the same or different.

L is a divalent linking group which may be selected from the group consisting of a direct bond, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

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According to another embodiment of the present invention, it is preferable that R ₁ and R ₂ are a substituted or unsubstituted pyridine group, a substituted or unsubstituted quinoline group, or a substituted or unsubstituted carbazole group.

Specific examples of the alkyl group as the substituent used in the present invention include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, a hexyl group, a heptyl group, A halogen atom, a hydroxyl group, a nitro group, a cyano group, a trifluoromethyl group, a silyl group (in this case, a " Substituted or unsubstituted amino group (-NH2, -NH (R), -N (R ') (R "), R' and R" A hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms An alkenyl group having 1 to 20 carbon atoms, an alkynyl group having 1 to 20 carbon atoms Heterocyclic group, which may be substituted with a heteroaryl group containing 6 to 30 carbon atoms of the aryl group, having 6 to 60 carbon atoms in the arylalkyl group, having 4 to 40 carbon atoms or a heteroaryl group of from 4 to 40.

Specific examples of the cycloalkyl group used as the substituent in the compound of the present invention include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, ≪ / RTI >

Specific examples of the alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, And can be substituted with substituents similar to those in the case of the alkyl group.

Specific examples of the halogen group which is a substituent used in the compound of the present invention include fluorine (F), chlorine (Cl), bromine (Br) and the like.

Specific examples of the aryl group as the substituent group used in the compound of the present invention include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, Examples of the aryl group include phenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, , Aromatic groups such as anthryl group, phenanthryl group, pyrenyl group, triphenylene group, chrysene group, fluororanthrene group, tetracene group, pentacene group, perylene group, fluorenyl group, and tetrahydronaphthyl group, May be substituted with the same substituent as in the case of the alkyl group.

Specific examples of the heteroaryl group used as the substituent in the compound of the present invention include pyridinyl, pyrimidinyl, triazinyl, indolinyl, quinolinyl, pyrrolidinyl, piperidinyl, An oxazolyl group, an oxadiazolyl group, a benzoxazolyl group, a thiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a triazolyl group, an imidazolyl group, or a benzoimidazole group, And at least one of the hydrogen atoms of the heteroaryl group may be substituted with the same substituent as the alkyl group.

As the alkenyl group used in the compound of the present invention, a vinyl group, a butadiene group, a hexatriene group, an octatetraene group and the like can be substituted with substituents similar to those in the case of the alkyl group.

As the alkynyl used in the compound of the present invention, there is an acetylene group or the like, and the substituent can be substituted with the same substituent as the alkyl group.

Specifically, the condensed aromatic compound according to the present invention may be any compound selected from the group consisting of compounds represented by the following formulas (2) to (85), but the present invention is not limited thereto.

[Chemical Formula 2] < EMI ID =

[Chemical Formula 5] < EMI ID =

[Chemical Formula 8]

[Chemical Formula 12] [Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 18] [Chemical Formula 19]

[Chemical Formula 20]

[Chemical Formula 23] [Chemical Formula 25]

[Chemical Formula 26]

[Chemical Formula 30] [Chemical Formula 30]

[Chemical Formula 32]

[Chemical Formula 35]

[Chemical Formula 38] [Chemical Formula 39]

[Chemical Formula 41]

[Chemical Formula 45]

[Chemical Formula 48] [Chemical Formula 48]

[Chemical Formula 50] [Chemical Formula 51]

[Chemical Formula 55] [Chemical Formula 55]

[Chemical Formula 57] [Chemical Formula 58]

[Chemical Formula 60] [Chemical Formula 61]

[Chemical Formula 62]

[Chemical Formula 65]

[Chemical Formula 70] [Chemical Formula 70]

[Chemical Formula 71] [Chemical Formula 72]

[Chemical Formula 75] [Chemical Formula 75]

[Formula 77] [Formula 79]

[Formula 80] [Formula 81]

[Chemical Formula 84]

According to another embodiment of the present invention, there is provided an organic electroluminescent device comprising a layer containing a condensed aromatic compound represented by the above-mentioned formulas (1-a) and (1-b) interposed between the anode and the cathode Lt; / RTI >

According to an embodiment of the present invention, at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer and an electron injecting layer is further interposed between the anode and the cathode And the compound represented by Formula 1-a and Formula 1-b is preferably contained in the electron transporting layer between the anode and the cathode, and the thickness of the electron transporting layer is preferably 50 to 2,000 ANGSTROM.

According to another embodiment of the present invention, at least one or more layers of the hole injection layer, the hole transport layer, the hole blocking layer, the light emitting layer, the electron transport layer, the electron injection layer and the electron blocking layer are formed by a solution process An organic electroluminescent device is provided.

The hole transport layer is laminated in order to facilitate the injection of holes from the anode. As the material of the hole transport layer, an electron donor molecule having a low ionization potential is used. The electron transport layer is mainly composed of diamine, triamine or tetra Amine derivatives are widely used.

In the present invention, the material for the hole transport layer is not particularly limited as long as it is commonly used in the art. For example, N, N'-bis (3-methylphenyl) -N, N'- , 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine (a-NPD).

A HIL (Hole Injection Layer) may be additionally deposited on the lower portion of the hole transport layer. The material for the hole injection layer is not particularly limited as long as it is commonly used in the art. For example, CuPc or starburst type amines such as TCTA and m-MTDATA may be used.

The light-emitting layer may be a layer in which electrons or holes injected from the electron-transporting layer and the hole-transporting layer are recombined to emit light, and the light-emitting layer may be within the layer of the light-emitting layer or may be the interface with the light-

The light emitting layer of the present invention preferably contains a host compound and a phosphorescent compound.

In addition, the electron transport layer used in the organic electroluminescent device according to the present invention can transport electrons supplied from the cathode smoothly to the organic luminescent layer and inhibit the movement of holes which are not bonded in the organic luminescent layer, . The material for the electron transport layer is not particularly limited as long as it is commonly used in the art. For example, the electron transport layer material can be used not only as a compound represented by the above formulas 1-a and 1-b, PBD, BMD, BND or Alq ₃ , which are sol derivatives, can be used.

On the other hand, an electron injection layer (EIL) may be further formed on the electron transport layer to facilitate injection of electrons from the cathode to ultimately improve power efficiency. As long as it is commonly used in the art, it can be used without any particular limitation. For example, materials such as LiF, NaCl, CsF, Li ₂ O, and BaO can be used.

The organic electroluminescent device according to one embodiment of the present invention can be used for a display device, a display device, an element for a single color or a white illumination, and the like.

1 is a cross-sectional view showing the structure of an organic electroluminescent device of the present invention. The organic light emitting diode according to the present invention includes an anode 20, a hole transporting layer 40, an organic light emitting layer 50, an electron transporting layer 60 and a cathode 80, An injection layer 70 may be further formed. In addition, one or two intermediate layers may be further formed, or a hole blocking layer or an electron blocking layer may be further formed.

Referring to FIG. 1, the organic electroluminescent device of the present invention and its manufacturing method will be described as follows. First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), and zinc oxide (ZnO), which are transparent and excellent in conductivity, are used.

A hole injection layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30. A hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method to form a thin film on the organic light emitting layer 50 can do. When the holes pass through the organic light emitting layer and enter the cathode, the lifetime and efficiency of the hole blocking layer are reduced. Therefore, the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO level. The hole blocking material used herein is not particularly limited, but it is required to have an ionization potential higher than that of a light emitting compound while having an electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. Here, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

Hereinafter, the present invention will be described in more detail with reference to the following Synthesis Examples, Examples and Comparative Examples, but the following examples are for illustrative purposes only and are not intended to limit the present invention.

Synthetic example  1: Synthesis of [Formula 3]

Synthetic example  1- (1) 2,7- Dibromophenanthrene -9,10- Dikton's  synthesis

10 g (0.048 mol) of phenanthrene-9,10-diketone was mixed with 200 mL of bromic acid (HBr) and 60 mL of sulfuric acid (H ₂ SO ₄ ) in a 250 mL round- Solution. The solution is heated with stirring at 80 DEG C for 24 hours. After the reaction, the resulting solid is filtered and washed with excess water. The solid was dried and recrystallized from toluene to give 12.82 g (yield 73%) of a yellow solid.

Synthetic example  1- (2) 6,11- Dibromo - Dibenzo [f, h] - Quinoxaline  synthesis

12.82 g (0.035 mol) of 2,7-dibromophenanthrene-9,10-diketone is added to 300 mL of anhydrous ethanol in a 1000 mL round bottom flask. To this solution was added 2.31 g (0.39 mol) of ethylenediamine. The solution was refluxed for 8 hours under a nitrogen atmosphere, and then 500 mL of acetic acid was added thereto, followed by refluxing for 9 hours. After cooling the reaction solution to room temperature, filter the resulting solid and wash with excess ethanol. 9.5 g of a solid was obtained (yield 70%).

Synthetic example  1- (3) Synthesis of [Formula 3]

(0.023 mol) of 6,11-dibromo-dibenzo [f, h] -quinoxaline, 7.13 g (0.058 mol) of pyridine-3-boronic acid, tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} 1.34g, potassium carbonate (K ₂ CO ₃₎ furan (THF) to 9.6g (0.070mol) in tetra hidi 50mL, 50mL dioxane, placed in 25mL of water is refluxed for 12 hours. After the reaction, the solution is cooled to room temperature and the resulting solid is filtered and washed with excess methanol. The solid was separated by column chromatography using hexane and diethyl acetate as eluent to obtain 5.7 g (yield 63.9%) of a white solid.

MS (MALDI-TOF): m / z 384.1 [M] ^< ⁺ & gt ^;

Synthetic example  2: Synthesis of [Formula 16]

(Yield: 54.2%) was obtained in the same manner as in Synthesis Example 1- (3), except that quinoline-3-boronic acid was used instead of pyridine-3-boronic acid in Synthesis Example 1- (3) .

MS (MALDI-TOF): m / z 484.1 [M] ^< ^{+ &}

Synthetic example  3: Synthesis of [Formula 45]

Synthetic example  3- (1) 3,6- Dibromophenanthrene -9,10- Dikton's  synthesis

10.2 g (0.098 mol) of phenanthrene-9,10-diketone and 0.87 g (0.004 mol) of dibenzoyl peroxide are added to 70 mL of nitrobenzene in a 250 mL round bottom flask. 15.9 g (0.099 mol) of bromine is added dropwise to the mixture. The solution is heated at 110 DEG C for 18 hours, cooled to room temperature, and the formed solid is filtered. The filtered solid was washed with excess hexane and used in the next reaction. 33 g (yield: 85%) of a yellow solid was obtained.

Synthetic example  3- (2) 7,10- Dibromo - Dibenzo [f, h] - Quinoxaline  synthesis

Except that 3,6-dibromophenanthrene-9,10-diketone was used instead of 2,7-dibromophenanthrene-9,10-diketone in Synthesis Example 1- (2) Dibromo-dibenzo [f, h] -quinoxaline (yield 73%) was synthesized using the same method as 1- (2).

Synthetic example  3- (3) Synthesis of [Formula 45]

Except that 6,11-dibromo-dibenzo [f, h] -quinoxaline was used instead of 6,11-dibromo-dibenzo [f, h] -quinoxaline in Synthesis Example 1- (3) (Yield: 58.2%) was synthesized by the same method as Synthesis Example 1- (3).

MS (MALDI-TOF): m / z 384.1 [M] ^< ⁺ & gt ^;

Synthetic example  4: Synthesis of [Formula 58]

Dibromo-dibenzo [f, h] -quinoxaline instead of 6,11-dibromo-dibenzo [f, h] -quinoxaline in Synthesis Example 1- (3) -3-boronic acid was used in place of quinoline-3-boronic acid in step (3), a compound of formula (58) (yield 67.4%) was synthesized.

MS (MALDI-TOF): m / z 484.1 [M] ^< ^{+ &}

Synthetic example  5: Synthesis of [Formula 66]

A 100mL round bottom flask carbazol 6.5g (0.039mol), 7,10- dibromo-dibenzo [f, h] - quinoxaline 6.0 g (0.015mol), BINAP 0.19g , NaO t Bu 3.72g (0.04 mol), tetrakis (triphenylphosphine) palladium (Pd (PPh _{3) 4)} In the 0.07g, 50ml of toluene and refluxed for 24 hours. When the reaction is completed, the organic solvent is distilled off under reduced pressure, and extracted with ethyl acetate and water. The organic layer was separated, the solvent was removed, and the resulting solid was washed with methanol. Separation by column chromatography using hexane and ethyl acetate (1: 3) as eluent gave 5.3 g (yield: 61%) of [Formula 66].

MS (MALDI-TOF): m / z 560.0 [M] ^< ⁺ & gt ^;

Synthetic example  6: Synthesis of [Formula 80]

Synthetic example  6- (1) 3- Bromophenanthrene -9,10- Dikton's Synthetic synthesis

3-Bromophenanthrene-9,10-diketone (yield 58%) was synthesized by a method known in the published patent WO 2006/063466.

Synthetic example  6- (2) 7- Bromo - Dibenzo [f, h] - Quinoxaline  synthesis

Except that 3-bromophenanthrene-9,10-diketone was used instead of 2,7-dibromophenanthrene-9,10-diketone in Synthesis Example 1- (2) Dibenzo [f, h] -quinoxaline (yield 72%) was synthesized by a similar method to 2).

Synthetic example  6- (3) Synthesis of [Formula 80]

Dibenzo [f, h] -quinoxaline instead of 6,11-dibromo-dibenzo [f, h] -quinoxaline in Synthesis Example 1- (3) (Yield: 57.2%) was synthesized in the same manner as in Synthesis Example 1- (3), except that phenyl-1,3-diboronic acid was used in place of boronic acid.

MS (MALDI-TOF): m / z 534.6 [M] ^< ^{+ &}

Example

Manufacture of organic light-emitting diodes

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. (300 Å), NPP (300 Å), CBP + Ir (ppy) ₃ (10%) (300 Å) on the ITO after the substrate was placed in a vacuum chamber and the base pressure was adjusted to 1 × 10 ^-6 torr. , A compound according to the present invention (350 Å), LiF (5 Å), and Al (1,000 Å).

Comparative Example

The organic light emitting diode device for the comparative example was fabricated in the same manner except that Alq ₃ was used instead of the compound manufactured by the invention in the device structure of the embodiment.

division The Dopant Doping concentration (%) V J (mA / cm 2) ㏅ / ㎡ CIEx CIEy Example 1 3 Ir (ppy) ₃ 10 4.05 10 5040 0.313 0.619 Example 2 16 Ir (ppy) ₃ 10 4.10 10 5213 0.312 0.621 Example 3 45 Ir (ppy) ₃ 10 4.34 10 5262 0.305 0.625 Example 4 58 Ir (ppy) ₃ 10 3.92 10 5372 0.304 0.625 Example 5 66 Ir (ppy) ₃ 10 4.41 10 5109 0.314 0.620 Example 6 80 Ir (ppy) ₃ 10 4.03 10 5250 0.308 0.623 Comparative Example Alq ₃ Ir (ppy) ₃ 10 7.93 10 3801 0.297 0.624

As shown in Table 1, the organic compound obtained according to the present invention exhibits low driving voltage and excellent luminous efficiency as compared with Alq ₃ , which is widely used as an ETL material.

10: substrate 20: anode
30: Hole injection layer 40: Hole transport layer
50: organic light emitting layer 60: electron transporting layer
70: electron injection layer 80: cathode

Claims (7)

A condensed aromatic compound represented by the following formula (1-b):
[Chemical Formula 1-b]

In the above formula (1-b)
R ₁ and R ₂ are each independently hydrogen, deuterium, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms,
R ₃ is hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms,
m and n are integers of 1 to 4, o is an integer of 1 to 2, and when m, n and o are larger than 2, plural R ₁ to R ₃ are each independently the same or different,
L is a substituted or unsubstituted arylene group having 6 to 40 carbon atoms or a substituted or unsubstituted divalent linking group having 3 to 20 carbon atoms and a heteroarylene group. The method according to claim 1,
The substituent of R ₁ to R ₃ and L (except when R ₁ to R ₃ are each hydrogen or deuterium) is any one selected from an aryl group having 6 to 24 carbon atoms and a heteroaryl group having 3 to 20 carbon atoms Or a condensed aromatic compound. delete The method according to claim 1,
A condensed aromatic compound represented by any one of the following formulas (80) to (85)

[Formula 80] [Formula 81]

[Chemical Formula 84] Anode;
Cathode; And
And a layer containing the condensed aromatic compound according to claim 1 interposed between the anode and the cathode. 6. The method of claim 5,
A hole injecting layer, a hole transporting layer, and an electron blocking layer between the anode and the cathode. And at least one layer selected from the group consisting of a light emitting layer, a hole blocking layer, an electron transporting layer, and an electron injecting layer. The method according to claim 6,
Wherein the condensed aromatic compound is contained in the electron transporting layer between the anode and the cathode.

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