KR20110120078A - Naphthalene derivatives and organic light-emitting diode including the same - Google Patents

Abstract

PURPOSE: A naphthalene derivative compound is provided to ensure excellent light-emitting properties and to obtain an organic electroluminescent device with excellent efficiency, driving voltage, stability, brightness and long lifetime. CONSTITUTION: A naphthalene derivative compound is represented by chemical formula 1, wherein R1 is selected from hydrogen, deuterium, substituted or unsubstituted C1-24 alkyl group and substituted or unsubstituted C6-24 aryl group; R2-R5 are selected from substituted or unsubstituted C1-24 alkyl group, substituted or unsubstituted C6-24 aryl group, and substituted or unsubstituted C2-24 heteroaryl group, wherein R2 and R3, and R4 and R5 are bonded to each other and can form a cyclic compound; X is selected from substituted or unsubstituted C1-3 alkylene, O, S, SO2, SiA1A2 and NR6; and n is an integer of 0-3.

Description

Naphthalene derivatives and organic light emitting device including the same {Naphthalene derivatives and organic light-emitting diode including the same}

The present invention relates to a novel naphthalene derivative which can be used as a light emitting layer material and an organic light emitting device including the same, and more particularly, a naphthalene derivative having a low driving voltage, excellent brightness and long life, and an organic light emitting device comprising the same. It is about.

Recently, as the size of the display device increases, the demand for a flat display device having a small space is increasing. A liquid crystal display, which is a typical flat display device, has a merit of being lighter than a conventional cathode ray tube (CRT), but the viewing angle The disadvantage is that the angle is limited and the back light is necessary.

In contrast, organic light emitting diodes (OLEDs), which are new flat panel display devices, are displays using self-luminous phenomena, and have a large viewing angle, are thinner and shorter than liquid crystal displays, and have fast response speeds. In recent years, application as a full-color display or lighting is expected.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.

An organic light emitting display device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device. For example, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows. Such organic light emitting diodes are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

The material used as the organic material layer in the organic electroluminescent device may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function. The light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. . In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.

On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect. A host-dopant system can be used as the luminescent material to increase the luminous efficiency through.

When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

In order for the organic electroluminescent device to fully exhibit the above-mentioned excellent features, the organic layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. is supported by a stable and efficient material Although this should be preceded, the development of a stable and efficient organic material layer for an organic light emitting device has not been made yet. Accordingly, there is a continuing need in the art for the development of new materials having low voltage driving, high efficiency, high brightness and long life.

Accordingly, the first technical problem to be solved by the present invention is to provide a naphthalene derivative having excellent brightness and long life.

The second technical problem to be solved by the present invention is to provide an organic light emitting device comprising a naphthalene derivative having excellent brightness and long life.

In order to achieve the first technical problem, the present invention provides a naphthalene derivative represented by the following [Formula 1].

[Formula 1]

In [Formula 1],

R ₁ is selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms and a substituted or unsubstituted aryl group having 6 to 24 carbon atoms,

R ₂ To R ₅ are each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms; ,

R ₂ and R ₃ , R ₄ and R ₅ may be connected to each other to form a ring compound,

X is substituted or unsubstituted alkylene having 1 to 3 carbon atoms, O, S, SO ₂ , SiA ₁ A ₂ And NR ₆ ,

A ₁ , A ₂ and R ₆ are the same as defined above for R ₁ ,

n is an integer of 0-3.

The present invention, in order to achieve the second technical problem, an anode; Cathode; And in the light emitting layer interposed between the anode and the cathode, the light emitting layer provides an organic electroluminescent device comprising a naphthalene derivative represented by the above [Formula 1].

According to another embodiment of the present invention, a pyrene-based compound represented by the following [Formula 98] may be further included as a guest compound in the light emitting layer including the naphthalene derivative represented by the above [Formula 1].

(98)

According to the present invention, since the naphthalene derivative compound represented by [Formula 1] has excellent luminous ability compared to the existing material, the organic electroluminescent device including the same shows excellent characteristics in terms of efficiency, driving voltage, stability, and particularly excellent brightness and It can provide long life and improve luminous efficiency.

1 is a schematic diagram of an organic light emitting display device according to an embodiment of the present invention.
<Description of the symbols for the main parts of the drawings>
10: substrate 20: anode
30: hole injection layer 40: hole transport layer
50: organic light emitting layer 60: electron transport layer
70: electron injection layer 80: cathode
FIG. 2 is a graph showing relative changes in luminance based on initial luminance values with time for organic light emitting diodes manufactured according to Examples 1 to 3 and Comparative Example 1. FIG. The X axis is Hours and the Y axis is luminance%.

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

The present invention is a novel naphthalene derivative having improved characteristics such as brightness and lifespan of a naphthalene derivative, which is conventionally used as a light emitting layer material, and is a compound represented by the above [Formula 1] structurally characterized in that various substituents are bonded to the naphthalene base skeleton It is done.

In the naphthalene derivative of the above [Formula 1] according to the present invention, the substituent is described in more detail as follows.

In [Formula 1], the substituents are each independently a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, a hydroxy group, a nitro group, an alkyl group having 1 to 40 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an alkyl having 1 to 40 carbon atoms Amino group, arylamino group having 6 to 40 carbon atoms, heteroarylamino group having 3 to 40 carbon atoms, alkylsilyl group having 1 to 40 carbon atoms, arylsilyl group having 6 to 40 carbon atoms, aryl group having 6 to 40 carbon atoms, aryl group having 3 to 40 carbon atoms It may be substituted by one or more substituents selected from the group consisting of an aryloxy group, a heteroaryl group having 3 to 40 carbon atoms, a germanium group, phosphorus and boron, and may be further substituted by the substituent.

R ₂ and R ₃ , R ₄ and R ₅ may be bonded to each other to form an aliphatic, aromatic, heteroaliphatic or heteroaromatic ring which is a saturated or unsaturated ring.

Specific examples of the alkyl group which is a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, heptyl, octyl, A stearyl group, a trichloromethyl group, a trifluoromethyl group, and the like, and at least one hydrogen atom of the alkyl group may be a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a trifluoromethyl group, or a silyl group (in this case, Alkylsilyl groups ", substituted or unsubstituted amino groups (-NH ₂ , -NH (R),-N (R ') (R"), wherein R, R' and R "are each independently carbon An alkyl group of 1 to 24 (in this case referred to as an "alkylamino group"), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group of 1 to 24 carbon atoms, a halogenated alkyl group of 1 to 24 carbon atoms , Alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, 1 carbon atom By more than 24 heteroaryl group, a heteroarylalkyl group having a carbon number of 5 to 24 aryl group, C 6 -C 24 aryl group, a C 3 -C 24 heteroaryl group, or having from 3 to 24 of which may be substituted.

Specific examples of the alkoxy group which is a substituent used in the compound of the present invention include methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group, hexyloxy group and the like. And it can be substituted with the same substituents as the case of the said 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 which is a substituent used in the compound of the present invention are phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, o-biphenyl group, m-biphenyl group, p-ratio Phenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, 2-naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group And an aromatic group such as an anthryl group, a phenanthryl group, a pyrenyl group, a fluorenyl group, a tetrahydronaphthyl group, and the like, and may be substituted with the same substituent as in the alkyl group.

Specific examples of the heteroaryl group which is a substituent used in the compound of the present invention include pyridinyl group, pyrimidinyl group, triazinyl group, indolinyl group, quinolinyl group, pyrrolidinyl group, piperidinyl group, morpholidinyl group, pipepe Radiinyl, carbazolyl, oxazolyl, oxdiazolyl, benzooxazolyl, chiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, imidazolyl and benzoimidazole At least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as in the alkyl group.

In the present invention, the term "substituted or unsubstituted" is aryl group, heteroaryl group, alkyl group, heteroalkyl group, cycloalkyl group, alkoxy group, cyano group, halogen group, aryloxy group, alkylsilyl group, arylsilyl group It means that it is unsubstituted or substituted with one or more substituents selected from the group consisting of germanium, phosphorus, boron, deuterium and hydrogen.

Although the present invention is not limited by the specific examples of the naphthalene derivative according to [Formula 1] having the structure as described above, specifically, any one of the compounds represented by the following [Formula 2] to [Formula 97] Can be.

[Formula 2] [Formula 3]

[Formula 4] [Formula 5]

[Formula 6] [Formula 7]

[Formula 8] [Formula 9]

[Formula 10] [Formula 11]

[Formula 12] [Formula 13]

[Formula 14] [Formula 15]

[Formula 16] [Formula 17]

[Formula 18] [Formula 19]

[Formula 20] [Formula 21]

[Formula 22] [Formula 23]

[Formula 24] [Formula 25]

[Formula 26] [Formula 27]

[Formula 28] [Formula 29]

[Formula 30] [Formula 31]

[Formula 32] [Formula 33]

[Formula 34] [Formula 35]

[Formula 36] [Formula 37]

[Formula 38] [Formula 39]

[Formula 40] [Formula 41]

[Formula 42] [Formula 43]

[Formula 44] [Formula 45]

[Formula 46] [Formula 47]

[Formula 48] [Formula 49]

[Formula 50] [Formula 51]

[Formula 52] [Formula 53]

[Formula 54] [Formula 55]

[Formula 56] [Formula 57]

[Formula 58] [Formula 59]

[Formula 60] [Formula 61]

[Formula 62] [Formula 63]

[Formula 64] [Formula 65]

[Formula 66] [Formula 67]

[Formula 68] [Formula 69]

[Formula 70] [Formula 71]

[Formula 72] [Formula 73]

[Formula 74] [Formula 75]

[Formula 76] [Formula 77]

[Formula 78] [Formula 79]

[Formula 80] [Formula 81]

[Formula 82] [Formula 83]

[Formula 84] [Formula 85]

[Formula 86] [Formula 87]

[Formula 88] [Formula 89]

[Formula 90] [Formula 91]

[Formula 92] [Formula 93]

[Formula 94] [Formula 95]

[Formula 96] [Formula 97]

The method for preparing a naphthalene derivative according to the present invention is shown in detail in the following examples.

In addition, the present invention is an anode; Cathode; And it is interposed between the anode and the cathode, and provides an organic electroluminescent device having a layer comprising a naphthalene derivative represented by the above [Formula 1].

The naphthalene derivative of Formula 1 may be used as the sole light emitting material or the light emitting host of the light emitting layer.

At this time, the layer containing the naphthalene derivative is preferably a light emitting layer between the anode and the cathode, and between the anode and the cathode as a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer It may further comprise one or more layers selected from the group consisting of.

In addition, according to another embodiment of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 kPa.

The light emitting layer may further include a guest material in addition to the naphthalene derivative used as a host material. Specific examples of the guest material include pyrene compounds, arylamines, peryl compounds, pyrrole compounds, hydrazone compounds, carbazole compounds, stilbene compounds, starburst compounds, oxadiazole compounds, coumarines, and the like. Although the present invention is not limited thereto, it is preferable to include a pyrene-based compound represented by the following [Formula 98].

(98)

As a specific example, a hole transport layer (HTL) may be further stacked, and an electron transport layer (ETL) may be additionally stacked between the cathode and the organic light emitting layer. The transport layer is laminated to facilitate the injection of holes from the anode. As the material of the hole transport layer, electron donating molecules having a small ionization potential are used. A diamine, triamine or tetraamine derivative mainly based on triphenylamine is used. Is used a lot.

The present invention is not particularly limited as long as it is commonly used in the art as a material of the hole transport layer. For example, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1 , 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine (a-NPD) and the like can be used.

A hole injection layer (HIL) may be further stacked on the lower portion of the hole transport layer. The hole injection layer material may also be used without particular limitation as long as it is commonly used in the art. For example, TCP (4,4 ', 4' '-tri (N-carbazolyl) triphenyl-amine), m-MTDATA (4,4', 4 ''-, which is a copper phthalocyanine (CuPc) or starburst type amine tris- (3-methylphenylphenyl amino) triphenylamine) may be used.

In addition, the electron transport layer used in the organic electroluminescent device according to the present invention has the opportunity to recombine in the light emitting layer by smoothly transporting the electrons supplied from the cathode to the organic light emitting layer and suppressing the movement of holes not bonded in the organic light emitting layer. Serves to increase.

The electron transport layer material may be used without particular limitation as long as it is commonly used in the art, and for example, oxadiazole derivatives such as PBD, BMD, BND or Alq ₃ may be used.

Meanwhile, an electron injection layer (EIL) may be further stacked on the electron transport layer to facilitate electron injection from the cathode and ultimately improve power efficiency. Also commonly used in the art may be used without particular limitation, for example, materials such as LiF, NaCl, CsF, Li ₂ O, BaO and the like can be used.

The organic light emitting display device according to the present invention can be used for a display device, a display device and a monochrome or white lighting device.

1 is a cross-sectional view showing the structure of an organic light emitting display device according to the present invention. The organic light emitting device according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60 and a cathode 80, and if necessary, the hole injection layer 30 and The electron injection layer 70 may be further included. In addition, an intermediate layer of one or two layers may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

Referring to Figure 1 with respect to the organic light emitting device and a method of manufacturing the present invention are as follows. First, the anode 20 is formed by coating an anode electrode material on the substrate 10. As the substrate 10, a substrate used in a conventional organic EL device is used. An organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness is preferable. As the anode electrode material, 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, are used.

The hole injection layer 30 is formed by vacuum-heat deposition or spin coating of the hole injection layer material on the anode 20 electrode. Next, the hole transport layer 40 is formed by vacuum thermal evaporation or spin coating of the hole transport layer material on the hole injection layer 30.

Subsequently, the organic light emitting layer 50 is stacked on the hole transport layer 40, and 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. can do. The hole blocking layer prevents such a problem by using a material having a very low highest Occupied Molecular Orbital (HOMO) level because when the hole is introduced into the cathode through the organic light emitting layer is reduced the lifetime and efficiency of the device. . In this case, the hole blocking material to be used is not particularly limited, but should have an ionization potential higher than the light emitting compound while having an electron transport ability, and typically BAlq, BCP, TPBI, and the like may be used.

After the electron transport layer 60 is deposited on the hole blocking layer through a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed and a cathode forming metal is vacuum-heated on the electron injection layer 70. The organic EL device is completed by vapor deposition to form a cathode 80 electrode. Here, the metal for forming the cathode may be lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lidium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag), and the like, and a transmissive cathode using ITO and IZO can be used to obtain a front light emitting device.

According to another embodiment of the present invention, at least one layer selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer is a single molecule deposition method or a solution process The organic light emitting display device according to the present invention may be used in display devices, display devices, and monochrome or white lighting devices.

Hereinafter, the present invention will be described in more detail with reference to preferred examples. However, these examples are intended to illustrate the present invention in more detail, and it will be apparent to those skilled in the art that the scope of the present invention is not limited thereto.

<Examples>

Synthesis Example 1 Synthesis of Compound Represented by Formula 2

(1) Synthesis of Compound Represented by [Formula 1-a]

The compound represented by [Formula 1-a] was synthesized by the following [Scheme 1].

Scheme 1

                                                 [Formula 1-a]

8.67ml (26.01mmol) of MeMgBr is dissolved in 50ml of THF, 2.7g (13.0mmol) of 6-bromo-1indanone is dissolved in 50ml of THF and dropwise stirred at 35-40 ° C for 15 hours. After the reaction, cool down, filter, and wash with THF. After stirring for 30 minutes in a 10% ammonium chloride solution, toluene 5ml, p -toluenesulfonicacidmonohydrate0.0125g was added, reflux cooled for 2 hours and washed with 2% Na ₂ CO ₃ to obtain a compound represented by [Formula 1-a]. (Yield 75%)

(2) Synthesis of Compound Represented by [Formula 1-b]

The compound represented by [Formula 1-b] was synthesized by the following [Scheme 2].

Scheme 2

    [Formula 1-a] [Formula 1-b]

Compound 2.1g (10.3 mmol), diphenyl amin 4.18g (24.73mmol) and t-BuONa 2.85g (27.67mmol) represented by [Formula 1-a] obtained from [Scheme 1] were added to 60 ml of O-xylene at room temperature Stir for 5 min at. (t-Bu) 3P 0.3g (1.64 mmol) and Pd (OAc) ₂ 0.09g (0.41mmol) were added and refluxed for 5 hours. After the reaction was completed, the mixture was cooled to room temperature. After adding MeOH, the mixture was stirred for 1 hour and filtered. The compound represented by [Formula 1-b] was obtained. (Yield 80%)

(3) Synthesis of Compound Represented by [Formula 1-c]

The compound represented by [Formula 1-c] was synthesized by the following [Scheme 3].

Scheme 3

  [Formula 1-b] [Formula 1-c]

Dissolve 3.3 g (7.28 mmol) of the compound represented by [Formula 1-b] obtained from the above [Scheme 2] in 20 ml of CHCl ₃ , and dissolve Br ₂ 1.16 g (7.28 mmol) in 20 ml of CCl ₄ for 10 minutes, and then at 0 ° C. Stir for 7 hours. The solvent was removed, pyridine 1.8g, toluene 10ml was added to the solid, refluxed for 3 hours, cooled, washed with 5% HCl, H ₂ O, and dried to obtain a compound represented by [Formula 1-c]. (60% yield)

(4) Synthesis of Compound Represented by [Formula 1-d]

The compound represented by [Formula 1-d] was synthesized by the following [Scheme 4].

Scheme 4

  [Formula 1-c] [Formula 1-d]

Dissolve 8.3 g (22.13 mmol) of the compound represented by [Formula 1-c] obtained from the above [Scheme 4] in 40 ml of THF, and slowly add dropwise n-BuLi (16.6 ml) while stirring at −95 ° C. Stir for 30 minutes while maintaining 95 ℃, add 9.03ml (44.26mmol) of dioxa-borolane at room temperature dropwise, stir for 1 hour, add cold saturated NH ₄ Cl50ml, extract with ether and separate with crude column [Formula 1-d] The compound represented by was obtained. (Yield 80%)

(5) Synthesis of Compound Represented by [Formula 1-e]

The compound represented by [Formula 1-e] was synthesized by the following [Scheme 5].

Scheme 5

                                          [Formula 1-e]

2,3-dibromo-naphthalene 7.07g (24.73mmol), diphenylamin 4.18g (24.73mmol) and t-BuONa 2.85g (27.67mmol) were put in 60ml of O-xylene and stirred at room temperature for 5 minutes (t-Bu) 3P 0.3g (1.64mmol) and Pd (OAc) ₂ 0.09g (0.41mmol) were added and refluxed for 5 hours. After the reaction, the mixture was cooled to room temperature, an excess of MeOH was added thereto, stirred for about 1 hour, and then filtered to obtain a compound represented by [Formula 1-e]. (Yield 80%)

(6) Synthesis of Compound Represented by Formula 2

The compound represented by [Formula 2] was synthesized by the following [Scheme 6].

Scheme 6

    [Formula 1-d] [Formula 1-e] [Formula 2]

0.87 g (1.93 mmol) of the compound represented by [Formula 1-d] obtained from [Scheme 4], 0.60 g (1.61 mmol) of the compound represented by [Formula 1-e] obtained from [Scheme 5], Pd ( 0.07 g (0.1 mmol) of dppf) Cl ₂ was added to 20 ml of THF, 30 ml of saturated NaHCO ₃ solution was added, stirred at 70 ° C. for 12 hours, and cooled to room temperature to obtain a compound represented by [Formula 2]. (Yield 80%)

MS (MALDI-TOF): m / z 590 [M] ⁺

Synthesis Example 2 Synthesis of Compound Represented by Formula 4

3-methyl-diphenyl amine was added instead of the amines of Synthesis Example 1 (3) and Synthesis Example 1 (5), and synthesized in the same manner as in Synthesis Example 1 to obtain a compound represented by [Formula 4]. (Yield 87%)

MS (MALDI-TOF): m / z 618 [M] ⁺

Synthesis Example 3 Synthesis of Compound Represented by Formula 3

N-Phenyl-1-Naphthyl amine was added instead of the amines of Synthesis Example 1 (3) and Synthesis Example 1 (5) and synthesized in the same manner as in Synthesis Example 1 to obtain a compound represented by [Formula 3] Got it. (Yield 87%)

MS (MALDI-TOF): m / z 690 [M] ⁺

<Examples 1 to 3> Preparation of an organic electroluminescent device comprising a compound synthesized by Synthesis Examples 1 to 3

The light emitting area of the ITO glass was patterned to have a size of 2 mm x 2 mm and then washed. After mounting the ITO glass in a vacuum chamber, the base pressure was 1 × 10 ⁻⁷ torr, and then CuPc (800 kPa) and α-NPD (300 kPa) were formed on the ITO, followed by compound according to the present invention. 98% of the compound represented by the formula [98] was then deposited to form Alq ₃ (350 kPa), LiF (5 kPa), and Al (500 kPa) in order to prepare an organic light emitting display device.

[CuPc]

[α-NPD]

[Alq ₃ ]

Comparative Example 1

The organic electroluminescent device for the comparative example uses the compound 9,10-di (1-naphthyl) anthracene represented by the following [Formula 98] as a host material in the device structure of the above embodiment as a host material The same was produced except.

(98)

division Voltage (V) Current density (㎃ / ㎠) Luminance (Cd / ㎡) CIEx CIEy T98 Example 1 4.12 10 856.1 0.14 0.16 66 Example 2 3.85 10 777.5 0.14 0.16 43 Example 3 4.01 10 792.7 0.14 0.14 42 Comparative Example 1 5.10 10 560 0.14 0.17 41

Voltage, current density, luminance, color coordinates, and lifetime of the organic light emitting diodes manufactured according to <Examples 1 to 3> and <Comparative Example 1> were measured, and the results are shown in the following [Table 1]. T98 means the time taken for the luminance to decrease to 98% of the initial luminance.

From the results of <Examples 1 to 3>, <Comparative Example 1> and [Table 1], the organic light emitting device including the compound represented by [Formula 1] according to the present invention has a low driving voltage, luminous efficiency Since it shows excellent characteristics, it can be seen that it can be usefully used for display devices, display devices, and lighting.

Claims (10)

Naphthalene derivative represented by the following [Formula 1]:
[Formula 1]

In [Formula 1],
R ₁ is selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms and a substituted or unsubstituted aryl group having 6 to 24 carbon atoms,
R ₂ To R ₅ are each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms; ,
R ₂ and R ₃ , R ₄ and R ₅ may be connected to each other to form a ring compound,
X is selected from the group consisting of substituted or unsubstituted alkylene having 1 to 3 carbon atoms, O, S, SO ₂ , SiA ₁ A ₂ and NR ₆ ,
A ₁ , A ₂ and R ₆ are the same as defined above for R ₁ ,
n is an integer of 0-3. The method of claim 1,
R ₁ to R ₆ , A ₁ and A ₂ in [Formula 1] are each independently a deuterium atom, a cyano group, a halogen atom, a hydroxyl group, a nitro group, an alkyl group having 1 to 40 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, An alkylamino group having 1 to 40 carbon atoms, an arylamino group having 6 to 40 carbon atoms, a heteroarylamino group having 3 to 40 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms And naphthalene derivatives which are substituted with at least one member selected from the group consisting of an aryloxy group having 3 to 40 carbon atoms, a heteroaryl group having 3 to 40 carbon atoms, a germanium group, phosphorus and boron. The method of claim 1,
A naphthalene derivative characterized in that the compound of any one selected from the group represented by [Formula 2] to [Formula 97]:
[Formula 2] [Formula 3]

[Formula 4] [Formula 5]

[Formula 6] [Formula 7]

[Formula 8] [Formula 9]

[Formula 10] [Formula 11]

[Formula 12] [Formula 13]

[Formula 14] [Formula 15]

[Formula 16] [Formula 17]

[Formula 18] [Formula 19]

[Formula 20] [Formula 21]

[Formula 22] [Formula 23]

[Formula 24] [Formula 25]

[Formula 26] [Formula 27]

[Formula 28] [Formula 29]

[Formula 30] [Formula 31]

[Formula 32] [Formula 33]

[Formula 34] [Formula 35]

[Formula 36] [Formula 37]

[Formula 38] [Formula 39]

[Formula 40] [Formula 41]

[Formula 42] [Formula 43]

[Formula 44] [Formula 45]

[Formula 46] [Formula 47]

[Formula 48] [Formula 49]

[Formula 50] [Formula 51]

[Formula 52] [Formula 53]

[Formula 54] [Formula 55]

[Formula 56] [Formula 57]

[Formula 58] [Formula 59]

[Formula 60] [Formula 61]

[Formula 62] [Formula 63]

[Formula 64] [Formula 65]

[Formula 66] [Formula 67]

[Formula 68] [Formula 69]

[Formula 70] [Formula 71]

[Formula 72] [Formula 73]

[Formula 74] [Formula 75]

[Formula 76] [Formula 77]

[Formula 78] [Formula 79]

[Formula 80] [Formula 81]

[Formula 82] [Formula 83]

[Formula 84] [Formula 85]

[Formula 86] [Formula 87]

[Formula 88] [Formula 89]

[Formula 90] [Formula 91]

[Formula 92] [Formula 93]

[Formula 94] [Formula 95]

[Formula 96] [Formula 97]

In [Formula 2] to [Formula 97],
A ₁ , A ₂ and R ₆ are the same as defined above for R ₁ , respectively. Anode;
Cathode;
And a layer interposed between the anode and the cathode, the layer including the naphthalene derivative according to any one of claims 1 to 3. The method of claim 4, wherein
The naphthalene derivative is an organic light emitting device, characterized in that contained in the light emitting layer between the anode and the cathode. The method of claim 5, wherein
The light emitting layer is an organic electroluminescent device, characterized in that it further comprises a pyrene-based compound represented by the following [Formula 98] as a guest compound.
[Formula 98]

The method of claim 5, wherein
An organic electroluminescent device further comprising at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer between the anode and the cathode. The method of claim 5, wherein
The thickness of the light emitting layer is an organic light emitting device, characterized in that 50 to 2,000 kPa. The method of claim 7, wherein
At least one layer selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer is formed by a single molecule deposition method or a solution process. The method of claim 4, wherein
The organic electroluminescent device is an organic electroluminescent device, characterized in that used for a display device, a display device, or a device for monochrome or white illumination.

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