KR20150043020A - Antracene derivatives and organic light-emitting diode including the same - Google Patents

Abstract

The present invention relates to an anthracene derivative and an organic light-emitting diode including the same and, more specifically, to a compound for an organic light-emitting diode represented by Chemical Formula A and an organic light-emitting diode including the same. [Chemical Formula A] In Chemical Formula A, R_1, R_2, m, n, and X_1 to X_7 are the same as described in the detailed description of the invention.

Description

TECHNICAL FIELD [0001] The present invention relates to an anthracene derivative and an organic light emitting device including the same.

TECHNICAL FIELD The present invention relates to an anthracene derivative and an organic light emitting device including the same, and more particularly, to an organic light emitting device having a long life and excellent device characteristics such as luminescence efficiency when used as a fluorescent host, And an organic light emitting device.

In recent years, the demand for a flat display device having a small space occupation has been increasing due to the enlargement of a display device. The liquid crystal display, which is a typical flat display device, has an advantage of being lighter than a conventional CRT (cathode ray tube) angle is limited and a back light is necessarily required. In contrast, an organic light emitting diode (OLED), a new flat display device, is a display using an auto-luminescent phenomenon and has advantages such as a large viewing angle, a light weight and a small size compared to a liquid crystal display, In recent years, application to a full-color display or illumination 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 device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight and may be classified into a fluorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism . Further, the light emitting material may be classified into blue, green, and red light emission depending on the emission color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host-dopant system can be used as a light-emitting material in order to increase the light-emitting efficiency through the light-emitting layer.

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 is shifted to the wavelength band of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant used.

On the other hand, as a conventional technique for improving the efficiency and lifespan characteristics of an organic light emitting device, Japanese Unexamined Patent Publication No. 10-1068224 (Sep. 28, 2011) discloses that an aryl group including deuterium is bonded to an anthracene, (Japanese Patent Application Laid-Open No. 10-1092006 (Dec. 12, 2011) discloses a technique relating to an organic electroluminescent device having excellent lifetime characteristics while improving and maintaining the properties of the anthracene structure. Discloses a technique relating to an organic light-emitting device including an anthracene derivative in a light emitting medium layer.

However, despite the fact that various kinds of compounds for use in the light emitting medium layer have been prepared including the above-mentioned conventional arts, there is a continuing need to develop stable, efficient and long-life organic compound layer materials for organic light emitting devices It is true.

Korean Patent Registration No. 10-1068224 (September 28, 2011)

Patent Registration No. 10-1092006 (December, 2011)

Accordingly, the first technical object of the present invention is to provide a compound for an organic light emitting device which can be used for an organic light emitting layer and has excellent device characteristics such as long life and luminescence efficiency.

A second object of the present invention is to provide an organic light emitting device comprising the compound.

In order to achieve the first technical object, the present invention provides an organic compound represented by the following formula (A) as a compound that can be used in a light emitting layer of an organic light emitting device.

(A)

In the above formula (A)

R ₁ and R ₂ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, A substituted or unsubstituted C1 to C30 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, A substituted or unsubstituted aryloxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroatom having 2 or 3 carbon atoms having O, N or S Lt; / RTI > to 50, heteroaryl, cyano, nitro, and halogen,

When m is an integer of 2 or more, each R ₁ is the same or different, and when n is an integer of 2 or more, each R ₂ is the same as or different from each other,

X ₁ to X ₇ are the same as R ₁ and R ₂ , respectively, wherein at least one of X ₁ to X ₇ is a substituted or unsubstituted 2-naphthyl group,

m is an integer of 1 to 5, n is an integer of 1 to 8,

The 'substituted' in the 'substituted or unsubstituted' refers to a group selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, An alkyl group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, An aryloxy group having 1 to 24 carbon atoms, an arylsilyl group, and an aryloxy group having 1 to 24 carbon atoms.

According to another aspect of the present invention, there is provided an organic light emitting display comprising a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode, And at least one compound represented by the formula (A).

According to the present invention, the compound represented by the formula (A) has a long life characteristic as compared with a conventional organic light emitting device material that can be used as a fluorescent host, and has an advantage of excellent device characteristics such as luminous efficiency.

1 is a schematic view of an organic light emitting device according to an embodiment of the present invention.
FIG. 2 is a graph showing life evaluation of a device according to an embodiment of the present invention. FIG.

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

The present invention provides a compound represented by the following formula (A) as an organic compound that can be used in a light emitting layer of an organic light emitting device.

(A)

In the above formula (A)

R ₁ and R ₂ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, A substituted or unsubstituted C1 to C30 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, A substituted or unsubstituted aryloxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroatom having 2 or 3 carbon atoms having O, N or S Lt; / RTI > to 50, heteroaryl, cyano, nitro, and halogen,

When m is an integer of 2 or more, each R ₁ is the same or different, and when n is an integer of 2 or more, each R ₂ is the same as or different from each other,

X ₁ to X ₇ are the same as R ₁ and R ₂ , respectively, wherein at least one of X ₁ to X ₇ is a substituted or unsubstituted 2-naphthyl group,

m is an integer of 1 to 5, n is an integer of 1 to 8,

The 'substituted' in the 'substituted or unsubstituted' refers to a group selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, An alkyl group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, An aryloxy group having 1 to 24 carbon atoms, an arylsilyl group, and an aryloxy group having 1 to 24 carbon atoms.

In consideration of the range of the alkyl or aryl group in the above "substituted or unsubstituted alkyl group having 1 to 24 carbon atoms" and "substituted or unsubstituted aryl group having 6 to 24 carbon atoms", it is preferable that the number of carbon atoms is 1 to 24 And the number of carbon atoms in the aryl group of 6 to 24 carbon atoms means the total number of carbon atoms constituting the alkyl moiety or aryl moiety when it is considered that the substituent is not substituted without considering the substituted moiety. For example, a phenyl group substituted with a butyl group at the para position should be considered to correspond to an aryl group having 6 carbon atoms substituted with a butyl group having a carbon number of 4.

An aryl group, which is a substituent used in the compound of the present invention, refers to an aromatic system composed of a hydrocarbon containing at least one ring, and when the aryl group has a substituent, it is fused with neighboring substituents to further form a ring .

Specific examples of the aryl group include aromatic groups such as phenyl, naphthyl, tetrahydronaphthyl and the like. At least one hydrogen atom of the aryl group may be substituted with a substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, , An amino group (-NH ₂ , -NH (R), -N (R ') (R "), R' and R" are independently an alkyl group having 1 to 10 carbon atoms and in this case an "alkylamino group" An alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms , A heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, or a heteroarylalkyl group having 2 to 24 carbon atoms.

The heteroaryl group, which is a substituent used in the compounds of the present invention, refers to a C 2 -C 24 ring aromatic system containing 1, 2 or 3 heteroatoms selected from N, O, P or S and the remaining ring atoms are carbon, The rings may be fused to form a ring. And at least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as the aryl group.

Specific examples of the alkyl group as a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl and the like. The atom may be substituted with the same substituent as in the case of the aryl group.

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, hexyloxy, At least one hydrogen atom in the alkoxy group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the silyl group used as the substituent in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl, Butylsilyl, dimethylpurylsilyl and the like, and at least one hydrogen atom of the silyl group may be substituted with the same substituent as the aryl group.

The anthracene derivative of the present invention may have one or two substituted or unsubstituted 2-naphthyl groups in the substituents X ₁ to X ₇ . That is, one or two of the substituents X ₁ to X ₇ are 2-naphthyl groups which are substituted or unsubstituted, and the remaining substituents may be substituents that the substituents R ₁ and R ₂ may have.

In addition, the anthracene derivative of the present invention can be obtained by replacing the hydrogen position of the aromatic ring in the substituted or unsubstituted 2-naphthyl group with deuterium or a substituted or unsubstituted 2-naphthyl group by replacing the substituent R ₁ with a substituent containing deuterium or deuterium, By replacing with a substituent containing deuterium, the longer life characteristics can be sphered.

More specifically, the anthracene derivative of the present invention can be represented by the following formula [A-1].

[A-1]

R ₁ , R ₂ , m and n in the above-mentioned formula (A-1) are as defined above,

Wherein R ₃ , X ₁ , X ₂ , X ₄ to X ₇ are the same as R ₁ and R ₂ ,

At least one of X ₁ , X ₂ and X ₄ to X ₇ may be a substituted or unsubstituted 2-naphthyl group.

That is, the anthracene derivative of the present invention is a compound wherein the 'substituted or unsubstituted 2-naphthyl group' is bonded to the 2, 3 or 5 to 8 positions in the naphthyl group bonded to the anthracene as shown in the following formula (B) .

[Chemical Formula B]

In the case of the anthracene derivative represented by the above formula (A-1), as shown in the following formula (C), the main skeleton axis (the axis denoted by a solid line in the compound) of the 'phenyl-anthracene- A 2-naphthyl group which is substituted or unsubstituted so as to deviate from the surface of the substrate, the crystal structure of the molecule can be changed more asymmetrically, so that the characteristics of the organic light emitting device can be improved.

≪ RTI ID = 0.0 &

The anthracene derivative of the present invention may be represented by the following formula (A-2).

 [A-2]

R ₁ , R ₂ , m and n in the above-mentioned formula (A-2) are as defined above,

R ₃ to R ₅ and X ₄ to X ₇ are the same as R ₁ and R ₂ ,

At least one of X ₄ to X ₇ may be a substituted or unsubstituted 2-naphthyl group.

That is, in the present invention, the anthracene derivative represented by the above formula (A-2) can be produced by reacting the above substituted or unsubstituted 2-naphthyl group at positions 5 to 8 in the naphthyl group bonded to the anthracene, As shown above, the anthracene derivative represented by the above formula (A-2) can change the crystal structure of the molecule more asymmetrically, thereby improving the characteristics of the organic light emitting device. The long-life effect of the device can be realized.

In the present invention, the substituents R ₁ and R ₂ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, an alkyl group having 1 to 5 carbon atoms; A cycloalkyl group having 3 to 12 carbon atoms; An aryl group having 6 to 10 carbon atoms;

And m and n may be 1 or 2, respectively.

Hereinafter, the anthracene derivative of the present invention may be any compound selected from the group consisting of the following [compounds 1] to [84] as an example, but the present invention is not limited thereto.

[Compound 1] [Compound 2] [Compound 3]

[Compound 4] [Compound 5] [Compound 6]

[Compound 7] [Compound 8] [Compound 9]

[Compound 10] [Compound 11] [Compound 12]

[Compound 13] [Compound 14] [Compound 15]

[Compound 16] [Compound 17] [Compound 18]

[Compound 19] [Compound 20] [Compound 21]

[Compound 22] [Compound 23] [Compound 24]

[Compound 25] [Compound 26] [Compound 27]

[Compound 28] [Compound 29] [Compound 30]

[Compound 31] [Compound 32] [Compound 33]

[Compound 34] [Compound 35] [Compound 36]

[Compound 37] [Compound 38] [Compound 39]

[Compound 40] [Compound 41] [Compound 42]

[Compound 43] [Compound 44] [Compound 45]

[Compound 46] [Compound 47] [Compound 48]

[Compound 49] [Compound 50] [Compound 51]

[Compound 52] [Compound 53] [Compound 54]

[Compound 55] [Compound 56] [Compound 57]

[Compound 58] [Compound 59] [Compound 60]

[Compound 61] [Compound 62] [Compound 63]

[Compound 64] [Compound 65] [Compound 66]

[Compound 67] [Compound 68] [Compound 69]

[Compound 70] [Compound 71] [Compound 72]

[Compound 73] [Compound 74] [Compound 75]

[Compound 76] [Compound 77] [Compound 78]

[Compound 79] [Compound 80] [Compound 81]

[Compound 82] [Compound 83] [Compound 84]

When the anthracene derivative of the present invention is employed between a pair of electrodes (an anode and a cathode), the compound represented by the above formula (A) is a compound having a structure of 2-naphthyl group in the main skeleton of the anthracene- Anthracene-naphthyl 'structure, the crystal structure of the molecule can be changed more asymmetrically, thereby increasing the luminous efficiency of the organic light emitting device and, in particular, the long life effect of the device.

In addition, it can have a high heat resistance and a long life characteristic for the line heat generated in the organic layer between the pair of electrodes, between the organic layers or between the organic layer and the electrode.

The present invention relates to a plasma display panel comprising a first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains at least one of the anthracene derivatives of the present invention.

In the present invention, "(organic layer) includes one or more compounds "," (organic layer) may include one kind of compound belonging to the scope of the present invention or two or more different compounds belonging to the category of the above compound Can be interpreted as "exist".

 At this time, the organic layer containing the compound of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer.

Also, in the present invention, the organic layer interposed between the first electrode and the second electrode may be a light emitting layer, and in this case, the light emitting layer may be composed of a host and a dopant.

In the present invention, the compound of formula (A) may be used as a host.

Specific examples of the dopant substance used in the light emitting layer include a pyrene-based compound, a deuterium-substituted pyrene-based compound, an arylamine, a deuterium-substituted arylamine, a peryl-based compound, a deuterium-substituted peryl- Substituted carbazole-based compounds, stilbene-based compounds, deuterated substituted stilbene-based compounds, starburst-based compounds, deuterium-substituted starburst-based compounds, deuterium- An oxadiazole-based compound, a deuterium-substituted oxadiazole-based compound, coumarine, deuterium-substituted coumarine, and the like, but the present invention is not limited thereto.

When the light emitting layer includes a host and a dopant, the dopant may be selected from the range of about 0.01 to about 20 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

In the present invention, at least one layer selected from the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer may be formed by a single molecular deposition method or a solution process, The organic light emitting element can be used for a display element, a display element, or a monochromatic or white illumination element.

More particularly, the organic light emitting device includes a flat panel display device; A flexible display device; Monochrome or white flat panel illumination devices; And a device for flexible illumination of a single color or a white color.

As a specific example of the present invention, a hole transport layer (HTL) is further stacked between the anode and the organic emission layer, and an electron transport layer (ETL) is added between the cathode and the organic emission layer The hole transport layer is laminated in order to facilitate 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, and mainly triphenylamine is used as a basic skeleton Triamine or tetraamine 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 hole injection layer (HIL) may be additionally formed 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, (4,4 ', 4 "-tri (N-carbazolyl) triphenylamine), m-MTDATA (4,4', 4" -tris- (3-methylphenylphenyl amino) triphenylamine) can be used.

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

The material of the electron transport layer is not particularly limited as long as it is commonly used in the art. For example, oxadiazole derivative PBD, BMD, BND or Alq ₃ Etc. may be used.

Meanwhile, 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. The electron injection layer material As long as it is commonly used in the related 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.

Hereinafter, the organic light emitting device of the present invention will be described with reference to FIG.

1 is a cross-sectional view showing the structure of an organic light emitting device of 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, 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 light emitting device of the present invention and a method of manufacturing the same will be described below. 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 ), zinc oxide (ZnO) and the like 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. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level . In this case, the hole blocking material to be used is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having 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.

In addition, according to a specific example of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 ANGSTROM, and the light emitting layer may be composed of a host and a dopant, and the compound of the present invention may be used as a host.

In this case, the dopant may be a compound represented by the following Chemical Formula 1 or Chemical Formula 2. At this time, the light emitting layer may further include various dopant materials.

   [Chemical Formula 1] < EMI ID =

Among the above-mentioned formulas (1) and (2)

A is a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, an optionally substituted arylene group having 6 to 60 carbon atoms , A substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms having a hetero atom O, N or S, and the like.

More specifically, A is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms or a single bond, preferably an anthracene, pyrene, phenanthrene, indenophenanthrene, klysene, naphthacene, Perylene, pentacene, and more particularly, the A may be a substituent represented by any one of the following formulas (A1) to (A10).

[Formula A1] [Formula A2] [Formula A3]

[Chemical Formula A4] [Chemical Formula A5] [Chemical Formula A6]

[Chemical formula A7] [Chemical formula A8] [Chemical formula A9]

(A10)

Wherein Z ₁ to Z ₂ in the formula [A3] are each independently selected from the group consisting of hydrogen, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted Or an unsubstituted or substituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted aryl group having 2 to 60 carbon atoms (Substituted or unsubstituted C1-C60 alkyl) amino group, or a substituted or unsubstituted C6-C60 aryl) amino group, a substituted or unsubstituted C1-C60 alkylamino group, , (Substituted or unsubstituted aryl group having 6 to 60 carbon atoms) amino group, and Z ₁ to Z ₂ are the same or different from each other and can form a condensed ring with adjacent groups.

In the above formula (1)

X ₁ and X ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a single bond, X ₁ and X ₂ may be bonded to each other,

Y ₁ and Y ₂ are each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted Or a substituted or unsubstituted C1 to C24 heteroalkyl group, a substituted or unsubstituted C3 to C24 cycloalkyl group, a substituted or unsubstituted C1 to C24 alkoxy group, a cyano group, a halogen group, a substituted or unsubstituted carbon number A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron, deuterium, and hydrogen. more selected species and, Y ₁ to Y ₂ each are the same or different each other, may form a fused ring group of the aliphatic, aromatic, aliphatic hetero, or aromatic heterocyclic group which are adjacent to each other It was.

Each of l and m is an integer of 1 to 20, and n is an integer of 1 to 4.

In the above formula (2)

C _y is a substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, and when b is 2 or more, each cycloalkane may be in a fused form, Each of which may be substituted with deuterium or alkyl, and may be the same as or different from each other.

In addition, Is a single bond or - [C (R ₅ ) (R ₆ )] _p -, and p is an integer of 1 to 3; when p is 2 or more, R ₅ and R ₆ are the same or different from each other;

Wherein _{R 1, R 2, R 3} , R 5 and R ₆ are, each independently, hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms , A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, Or beach (Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms), a di (substituted or unsubstituted alkyl group having 1 to 60 carbon atoms) amino group, a substituted or unsubstituted amino group having 6 to 60 carbon atoms, An aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron,

a is an integer of 1 to 4, and when a is 2 or more, R ₃ of 2 or more are the same or different, and R ₃ Each R ₃ may be in fused form, and n is an integer from 1 to 4.

The amine group bonded to A in the formulas (1) and (2) may be represented by any one selected from the group consisting of the following [substituents 1] to [52], but is not limited thereto.

[Substituent 1] [Substituent 2] [Substituent 3]

[Substituent group 4] [Substituent group 5] [Substituent group 6]

[Substituent group 7] [Substituent group 8] [Substituent group 9]

[Substituent group 10] [Substituent group 11] [Substituent group 12]

[Substituent group 13] [Substituent group 14] [Substituent group 15]

[Substituent group 16] [Substituent group 17] [Substituent group 18]

[Substituent group 19] [Substituent group 20] [Substituent group 21]

[Substituent group 22] [Substituent group 23] [Substituent group 24]

[Substituent group 25] [Substituent group 26] [Substituent group 27]

[Substituent group 28] [Substituent group 29] [Substituent group 30]

[Substituent group 31] [Substituent group 32] [Substituent group 33]

[Substituent group 34] [Substituent group 35] [Substituent group 36]

[Substituent group 37] [Substituent group 38] [Substituent group 39]

[Substituent group 40] [Substituent group 41] [Substituent group 42]

[Substituent group 43] [Substituent group 44] [Substituent group 45]

[Substituent group 46] [Substituent group 47] [Substituent group 48]

[Substituent group 49] [Substituent group 50] [Substituent group 51]

[Substituent 52]

In the above substituents, R may be the same or different from each other and is selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted C1 to C60 alkoxy group, A substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, (Substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or a substituted or unsubstituted aryl (having 6 to 60 carbon atoms) amino group, di (substituted or unsubstituted A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, and each has 1 To 12 carbon atoms, and each of the substituents may form a condensed ring with adjacent groups.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent, however, to those skilled in the art that these embodiments are for further explanation of the present invention and that the scope of the present invention is not limited thereby.

<Examples>

Synthesis Example 1 Synthesis of BH1

Synthesis Example 1-1. Synthesis of intermediate 1-a

                     Intermediate 1-a

30 g (0.16 mol) of 1,7-dimethoxynaphthalene was added to a 500 mL four-neck round bottom flask, and 300 mL of acetonitrile was added to dissolve it. The temperature was cooled to 0 ° C and 28.4 g (0.16 mol) of N-bromosuccinmide was dissolved in 60 mL of acetonitrile and slowly added dropwise. The temperature was raised to room temperature and stirred for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and recrystallized from dichloromethane and hexane to obtain Intermediate 1-a (30 g, 70%).

Synthesis Example 1-2. Synthesis of Intermediate 1-b

      Intermediate 1-a Intermediate 1-b

30 g (0.11 mol) of Intermediate 1-a was placed in a 1000 L four-neck round bottom flask and 300 mL of dichloromethane was added to dissolve. The temperature was cooled to -78 ° C and 56.4 g (0.23 mol) of boron tribromide was diluted in 30 mL of dichloromethane and slowly added dropwise. The mixture was stirred at room temperature for 6 hours. After completion of the reaction, 300 mL of sodium bicarbonate aqueous solution was added and stirred for 30 minutes. The mixture was concentrated under reduced pressure, and recrystallized from dichloromethane and hexane to obtain intermediate 1-b (25 g, 82%).

Synthesis Example 1-3. Synthesis of Intermediate 1-c

                                   Intermediate 1-c

L 10 4 400 9-bromo-anthracene-gu round bottom flask g (1.55 mol), Pd ( PPh 3) 4 35.99 g (0.031 mol), potassium carbonate and 430.7 g (3.11 mol), phenylboronic acid 246.6 g (2.02 mol ), 2000 mL of toluene, 2000 mL of 1,4-dioxane and 1000 mL of water were added, and the mixture was refluxed for 16 hours. When the reaction was completed, the reaction mixture was concentrated under reduced pressure and recrystallized from toluene and methanol to obtain intermediate 1-c (298 g, 75%).

Synthesis Example 1-4. Synthesis of intermediate 1-d

        Intermediate 1-c Intermediate 1-d

298 g (1.17 mol) of intermediate 1-c was placed in a 10 L round bottom flask and 4000 mL of dichloromethane was added to dissolve. 0.0 &gt; 0 C &lt; / RTI &gt; and 206 g (1.29 mol) of bromine was slowly added dropwise. The temperature was raised to room temperature and stirred for 2 hours. After completion of the reaction, 1000 mL of an aqueous solution of sodium hydrogencarbonate was added and the mixture was stirred for 30 minutes. The mixture was concentrated under reduced pressure and recrystallized from dichloromethane and methanol to obtain intermediate 1-d (313 g, 80%).

Synthesis Example 1-5. Intermediate 1-e Synthesis

     Intermediate 1-d Intermediate 1-e

Add 280 g (0.84 mol) of Intermediate 1-d and 3000 mL of THF to a 10 L 4-neck round bottom flask and keep the temperature at -78 ° C. 1.6 M n-BuLi 630 mL is slowly added dropwise and stirred for 2 hours, then trimethylborate is added dropwise at the same temperature. The temperature is raised to room temperature and stirred for 12 hours. When the reaction is complete, add 2 N HCl. The organic layer was separated, neutralized and recrystallized with toluene to obtain Intermediate 1-e (228 g, 91%).

Synthesis Example 1-6. Synthesis of Intermediate 1-f

  Intermediate 1-b Intermediate 1-e Intermediate 1-f

1 L 4 gu intermediate 1-b To a round bottom flask was added 25 g (0.105 mol), Pd (PPh 3) 4 6 g (5 mmol), potassium carbonate 36.1 g (0.26 mol), intermediate 1-e 34.3 g (0.115 mol ), 150 mL of toluene, 150 mL of 1,4-dioxane and 75 mL of water were added, and the mixture was refluxed for 12 hours. When the reaction was completed, the reaction mixture was concentrated under reduced pressure and recrystallized from toluene and heptane to obtain intermediate 1-f (20.7 g, 48%).

Synthesis Example 1-7. Synthesis of intermediate 1-g

        Intermediate 1-f Intermediate 1-g

20 g (48 mmol) of Intermediate 1-f was placed in a 500 mL four-neck round bottom flask and dissolved in 200 mL of dichloromethane. 9.5 g (0.12 mol) of pyridine were added and the reaction was cooled to 0 &lt; 0 &gt; C. (CF ₃ SO ₂ ) ₂ O (30.1 g, 0.11 mol) was slowly added dropwise thereto, followed by stirring at room temperature for 1 hour and then adding 150 mL of water. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and then separated by column chromatography to obtain Intermediate 1-g (21.5 g, 65%).

Synthesis Example 1-8. [Chemical Formula 1] Synthesis

Intermediate 1-g [Chemical Formula 1]

1 L 4 gu intermediate 1-g 21.5 g (32 mmol ) in a round bottom _{flask, Pd (PPh 3) 4 3.7} g (3 mmol), 19.8 of potassium carbonate g (0.14 mol), 2-naphthyl boronic acid (2 naphthyl boronic acid (12.6 g, 75 mmol), 150 mL of toluene, 150 mL of 1,4-dioxane and 75 mL of water were added, and the mixture was refluxed for 12 hours. When the reaction was completed, the reaction mixture was concentrated under reduced pressure, and recrystallized from toluene and heptane to obtain 13 g (65%) of the compound of formula (1).

_{^{[1 H NMR (CDCl 3)}} : d 8.14 (Ar-H, d, 1H), d 8.01 ~ 7.89 (Ar-H, m, 14H), d 7.73 (Ar-H, m, 2H), d 7.59 ~ 7.39 (Ar-H, m, 15H), m / z: 632.25]

Synthetic example  2. Synthesis of chemical formula [2]

Synthesis Example 2-1. Synthesis of intermediate 2-a

                                        Intermediate 2-a

500 mL round bottom flask, 3-bromo-1-naphthol (3-bormo-1-naphthol ) 30 g (0.13 mol), Pd (PPh 3) 4 3.11 g (3 mmol), potassium carbonate and 37 g (0.26 mol ), And 24.3 g (0.14 mol) of 2-naphthyl boronic acid were added thereto, and 150 mL of toluene, 150 mL of 1,4-dioxane and 60 mL of water were added and refluxed for 16 hours. When the reaction was completed, the organic layer was separated and the aqueous layer was extracted twice with 100 mL of toluene. The combined organic layers were concentrated under reduced pressure and recrystallized from toluene and methanol to obtain intermediate 2-a (16 g, 44%).

Synthesis Example 2-2. Synthesis of intermediate 2-b

                                            Intermediate 2-b

In a 500 mL four-neck round bottom flask, add 16 g (59 mmol) of intermediate 2-a and 160 mL of dichloromethane to dissolve. 6.1 g (77 mmol) of pyridine was added and the mixture was cooled to 0 占 폚. (CF ₃ SO ₂ ) ₂ O (18.4 g, 65 mmol) was slowly added dropwise thereto, and then the mixture was stirred at room temperature for 1 hour and 150 mL of water was added thereto. The mixture was concentrated under reduced pressure and then separated by column chromatography to obtain intermediate 2-b (19.5 g, 82%).

Synthesis Example 2-3. Synthesis of intermediate 2-c

                                     Intermediate 2-c

10 L 4 gu 9-bromo-anthracene, 400 g (1.55 mol), Pd (PPh 3) To a round bottom flask was added ₄ 35.99 g (0.031 mol), potassium carbonate and 430.7 g (3.11 mol), 3- methylphenyl boronic acid 274.6 g ( 2.02 mol), 2000 mL of toluene, 2000 mL of 1,4-dioxane and 1000 mL of water were added, and the mixture was refluxed for 16 hours. When the reaction was completed, the reaction mixture was concentrated under reduced pressure and recrystallized from toluene and methanol to obtain Intermediate 2-c (303.6 g, 73%).

Synthesis Example 2-4. Synthesis of intermediate 2-d

   Intermediate 2-c Intermediate 2-d

314 g (1.17 mol) of intermediate 2-c was placed in a 10 L round bottom flask and 4000 mL of dichloromethane was added to dissolve. 0.0 &gt; 0 C &lt; / RTI &gt; and 206 g (1.29 mol) of bromine was slowly added dropwise. The temperature was raised to room temperature and stirred for 2 hours. After completion of the reaction, 1000 mL of an aqueous solution of sodium hydrogen carbonate was added and the mixture was stirred for 30 minutes. The mixture was concentrated under reduced pressure and recrystallized from dichloromethane and methanol to obtain intermediate 2-d (317 g, 78%).

Synthesis Example 2-5. Intermediate 2-e Synthesis

   Intermediate 2-d Intermediate 2-e

Add 292 g (0.84 mol) of intermediate 2-d and 3000 mL of THF to a 10 L round bottom flask and keep the temperature at -78 ° C. 1.6 M n-BuLi 630 mL is slowly added dropwise and stirred for 2 hours, then trimethylborate is added dropwise at the same temperature. The temperature is raised to room temperature and stirred for 12 hours. When the reaction is complete, add 2 N HCl. The organic layer was separated and neutralized and recrystallized with toluene to obtain intermediate 2-e (210 g, 90%).

Synthesis Example 2-6. [Chemical Formula 2] Synthesis

   Intermediate 2-b Intermediate 2-e [Chemical Formula 2]

300 mL 4 gu Intermediate To a round bottom flask was added 2-b 19 g (48 mmol ), Pd (PPh 3) 4 2.8 g (2 mmol), potassium carbonate 13.4 g (97 mmol), intermediate 2-e 16.5 g (53 mmol ), 100 mL of toluene, 100 mL of 1,4-dioxane and 50 mL of water were added, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and recrystallized from toluene and methanol to obtain 15 g (61%) of the compound of the formula (2).

_{^{[1 H NMR (CDCl 3)}} : d 8.55 (Ar-H, d, 2H), d 8.08 ~ 7.85 (Ar-H, m, 9H), d 7.76 ~ 7.73 (Ar-H, m, 2H), d 7.59 ~ 7.39 (Ar-H, m, 14H), d 2.4 (CH 3, s, 3H), m / z: 520.22]

Synthesis Example 3 . Synthesis of Chemical Formula [3]

Synthesis Example 3-1. Synthesis of intermediate 3-a

                              Intermediate 3-a

1000 mL round bottom flask, 1,5-dibromo-naphthalene (1,5-dibromonatphthalene) 35 g ( 0.12 mol), Pd (PPh 3) 4 7.08g (6 mmol), potassium carbonate 38.91 g (0.28 mol), 2 (2-naphthyl boronic acid), 210 mL of toluene, 210 mL of 1,4-dioxane and 100 mL of water were added, and the mixture was refluxed for 16 hours. When the reaction was completed, the organic layer was separated and the aqueous layer was extracted twice with 100 mL of toluene. The combined organic layers were concentrated under reduced pressure and separated by column chromatography to obtain intermediate 3-a (20 g, 50%).

Synthesis Example 3-2. [Chemical Formula 3] Synthesis

중간체 3-a 중간체 1-e [화학식 3]

Intermediate 3-a Intermediate 1-e &lt; EMI ID =

300 mL 4 gu Intermediate To a round bottom flask was added 3-a 10 g (3 mmol ), Pd (PPh 3) 4 1.74 g (2 mmol), potassium carbonate 9.54 g (69 mmol) and intermediate 1-e 11.63 g (39 mmol ), 60 mL of toluene, 60 mL of 1,4-dioxane and 30 mL of water were added, and the mixture was refluxed for 12 hours. When the reaction was completed, the reaction mixture was concentrated under reduced pressure, and recrystallized from toluene and methanol to obtain 8 g (53%) of the compound of formula (3).

_{^{[1 H NMR (CDCl 3)}} : d 8.51 (Ar-H, d, 2H), d 8.42 (Ar-H, d, 2H), d 8.00 ~ 7.91 (Ar-H, m, 7H), d 7.73 ( (Ar-H, d, 1 H), d 7.61-7.39 (Ar-H, m,

Synthetic example  4. Synthesis of chemical formula [4]

Synthesis Example 4-1. Synthesis of intermediate 4-a

Intermediate 4-a

25 g (0.15 mol) of 1-amino-6-naphthol and 110 mL of acetic acid were added to a 1000 mL round bottom flask, and the temperature was cooled to 0 占 폚. 50 mL of sulfuric acid was added dropwise, and then an aqueous solution in which 19.5 g (0.28 mol) of sodium nitrite was dissolved in 130 mL of water was slowly added dropwise. After the temperature was raised to room temperature, the mixture was stirred for 1 hour and then cooled to 0 ° C. Then, 0.8 g of urea and 91.1 g (0.55 mol) of potassium iodide were dissolved in 130 mL of water and slowly added dropwise. The temperature was raised to room temperature and stirred for 24 hours. When the reaction was completed, the organic layer was separated and the aqueous layer was extracted twice with 500 mL of dichloromethane. The combined organic layers were concentrated under reduced pressure and separated by column chromatography to obtain intermediate 4-a (18 g, 42%).

Synthesis Example 4-2. Intermediate 4-b Synthesis

Intermediate 4-a Intermediate 1-e Intermediate 4-b

300 mL intermediate 4-a 15 g (56 mmol ), Pd (PPh 3) 4 3.2 g (3 mmol), potassium carbonate 19.2 g (0.13 mol), intermediate 1-e 18.2 g (61 mmol ) in a round bottom flask, the 90 mL of toluene, 90 mL of 1,4-dioxane and 45 mL of water were added, and the mixture was refluxed for 16 hours. When the reaction was completed, the organic layer was separated and the aqueous layer was extracted twice with 100 mL of toluene. The combined organic layers were concentrated under reduced pressure and separated by column chromatography to give intermediate 4-b (10 g, 45%).

Synthesis Example 4-3. Intermediate 4-c Synthesis

   Intermediate 4-b Intermediate 4-c

10 g (25 mmol) of Intermediate 4-b was added to a 300 mL four-neck round bottom flask and dissolved in 100 mL of dichloromethane. 2.59 g (32 mmol) of pyridine were added and the reaction was cooled to 0 &lt; 0 &gt; C. (CF ₃ SO ₂ ) ₂ O (7.83 g, 27 mmol) was slowly added dropwise thereto, followed by stirring at room temperature for 1 hour, followed by the addition of 100 mL of water. Concentration under reduced pressure and separation by column chromatography gave Intermediate 4-c (10 g, 75%).

Synthesis Example 4-4. [Chemical Formula 4] Synthesis

   Intermediate 4-c [Chemical formula 4]

300 mL 4 gu intermediate 4-c To a round bottom flask was added 10 g (19 mmol), Pd (PPh 3) 4 1.1 g (0.001 mol), potassium carbonate 6.5 g (47 mmol), 2- naphthyl boronic acid (2 3.3 g (19 mmol) of naphthyl boronic acid were added, 60 mL of toluene, 60 mL of 1,4-dioxane and 30 mL of water were added, and the mixture was refluxed for 12 hours. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure, and recrystallized from toluene and methanol to obtain [Chemical Formula 4] (5.5 g, 57%).

_{^{[1 H NMR (CDCl 3)}} : d 8.42 (Ar-H, d, 1H), d 8.14 (Ar-H, d, 1H), d 8.04 ~ 7.89 (Ar-H, m, 10H), d 7.73 ( (Ar-H, d, 1 H), d 7.61-7.39 (Ar-H, m, 13H)

Synthesis Example 5. Synthesis of the chemical formula [5]

Synthesis Example 5-1. Synthesis of intermediate 5-a

Intermediate 5-a

25 g (0.15 mol) of 8-amino-2-naphthol and 110 mL of acetic acid were added to a 1000 mL round bottom flask, and the temperature was cooled to 0 占 폚. 50 mL of sulfuric acid was added dropwise, and then an aqueous solution in which 19.5 g (0.28 mol) of sodium nitrite was dissolved in 130 mL of water was slowly added dropwise. The temperature was raised to room temperature and stirred for 1 hour. After cooling to 0 ° C, 0.8 g of urea was added, and 91.1 g (0.55 mol) of potassium iodide was dissolved in 130 mL of water and slowly added dropwise. The temperature was raised to room temperature and stirred for 24 hours. After completion of the reaction, the reaction mixture was extracted twice with 500 mL of dichloromethane and concentrated under reduced pressure. Separation by column chromatography gave intermediate 5-a (20 g, 47%).

Synthesis Example 5-2. Intermediate 5-b Synthesis

중간체 5-a 중간체 1-e 중간체 5-b

Intermediate 5-a Intermediate 1-e Intermediate 5-b

300 mL intermediate 5-a 15 round bottomed flask g (56 mmol), Pd ( PPh 3) 4 3.2 g (3 mmol), potassium carbonate 19.2 g (0.13 mol), intermediate 1-e 18.2 g (61 mmol ), 90 mL of toluene, 90 mL of 1,4-dioxane and 45 mL of water were added, and the mixture was refluxed for 16 hours. When the reaction was completed, the organic layer was separated and the aqueous layer was extracted twice with 100 mL of toluene. The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain intermediate 5-b (13 g, 60%).

Synthesis Example 5-3. Intermediate 5-c Synthesis

         Intermediate 5-b Intermediate 5-c

10 g (25 mmol) of Intermediate 5-b was added to a 300 mL four-neck round bottom flask and dissolved in 100 mL of dichloromethane. 2.59 g (32 mmol) of pyridine were added and the reaction was cooled to 0 &lt; 0 &gt; C. (CF ₃ SO ₂ ) ₂ O (7.83 g, 27 mmol) was slowly added dropwise, the temperature was raised to room temperature, stirred for 1 hour, and 100 mL of water was added.

The organic layer was separated, concentrated under reduced pressure, and then separated by column chromatography to obtain Intermediate 5-c (9 g, 67%).

Synthesis Example 5-4. [Chemical Formula 5] Synthesis

   Intermediate 5-c [Chemical formula 5]

300 mL 4 gu intermediate 5-c To a round bottom flask was added 9 g (17 mmol), Pd (PPh 3) 4 1 g (0.001 mol), 5.9 Potassium carbonate g (43 mmol), 2-naphthyl boronic acid (2 naphthyl boronic acid (2.9 g, 17 mmol), toluene (55 mL), 1,4-dioxane (55 mL) and water (30 mL) were added, and the mixture was refluxed for 12 hours. After the reaction was completed, the reaction mixture was concentrated under reduced pressure and recrystallized from toluene and methanol to obtain 5 g (58%) of the compound of the formula (5).

_{^{[1 H NMR (CDCl 3)}} : d 8.42 (Ar-H, d, 1H), d 8.14 (Ar-H, d, 1H), d 8.04 ~ 7.89 (Ar-H, m, 10H), d 7.79 ( (Ar-H, d, 1 H), d 7.59 (Ar-H, m, 2H), d 7.58-7.39

Device fabrication and evaluation: Example  1 to 5

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. After the substrate was mounted in a vacuum chamber, the substrate was adjusted to have a pressure of 1 × 10 ^-6 torr, and DNTPD (700 Å) and α-NPD (300 Å) were deposited on the ITO. to formula (V) (example 1-5) a and the dopant of the bit BD1 (3 wt%), a co-deposited (300 Å) was, after the Alq ₃ (350 Å), LiF (5 Å), Al (1,000 Å ), And measurements were made at 0.4 mA.

The DNTPD, the structure of the α-NPB, Alq BD1 and ₃ are as follows.

        [DNTPD] [[alpha] -NPD]

[BD1] [Alq _3]

Comparative Examples 1 to 2

(Comparative Example 1) and [Compound B] (Comparative Example 2) were used instead of the host compound prepared by the invention in the device structures of Examples 1 to 5, And the structure is as follows.

[Compound A] [Compound B]

The voltage, efficiency, luminance, color coordinates, and lifetime of the organic light emitting device manufactured according to Examples 1 to 5 and Comparative Examples 1 and 2 were measured, and the results are shown in Table 1 below.

[V]
[cd / A] EQE cd / m ² CIE_x CIE_y lambda max LT97 Comparative Example 1
3.961 6.4 7.2 641.0 0.136 0.118 458 20.0 Comparative Example 2
3.981 6.5 7.4 653.7 0.136 0.118 458 25.7 Example 1
3.728 7.5 8.5 747.9 0.133 0.124 459 56.1 Example 2
3.827 7.3 8.7 734.2 0.134 0.116 458 51.0 Example 3
3.802 7.5 8.4 750.5 0.133 0.126 460 69.7 Example 4
3.843 7.3 8.9 730.2 0.135 0.112 458 50.4 Example 5
3.834 7.4 8.6 738.5 0.134 0.115 459 52.8

As shown in Table 1, the organic electroluminescent device including the organic electroluminescent compound according to the present invention has a low driving voltage and is excellent in light emission characteristics such as brightness and longevity, and can be utilized in various display devices.

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 (13)

An anthracene derivative represented by the following formula (A).
(A)

In the above formula (A)
R ₁ and R ₂ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, A substituted or unsubstituted C1 to C30 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, A substituted or unsubstituted aryloxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms A substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroatom having 2 or 3 carbon atoms having O, N or S Lt; / RTI &gt; to 50, heteroaryl, cyano, nitro, and halogen,
When m is an integer of 2 or more, each R ₁ is the same or different, and when n is an integer of 2 or more, each R ₂ is the same as or different from each other,
X ₁ to X ₇ are the same as R ₁ and R ₂ , respectively, wherein at least one of X ₁ to X ₇ is a substituted or unsubstituted 2-naphthyl group,
m is an integer of 1 to 5, n is an integer of 1 to 8,
The 'substituted' in the 'substituted or unsubstituted' refers to a group selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, An alkyl group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, An aryloxy group having 1 to 24 carbon atoms, an arylsilyl group, and an aryloxy group having 1 to 24 carbon atoms. The method according to claim 1,
An anthracene derivative represented by the above formula (A-1).
[A-1]

Wherein R ₁ , R ₂ , m and n are as defined in claim 1,
Wherein R ₃ , X ₁ , X ₂ , X ₄ to X ₇ are the same as R ₁ and R ₂ ,
At least one of X ₁ , X ₂ and X ₄ to X ₇ is a substituted or unsubstituted 2-naphthyl group. The method according to claim 1,
An anthracene derivative represented by the above-mentioned formula (A-2).
[A-2]

Wherein R ₁ , R ₂ , m and n are as defined in claim 1,
R ₃ to R ₅ and X ₄ to X ₇ are the same as R ₁ and R ₂ ,
At least one of X ₄ to X ₇ is a substituted or unsubstituted 2-naphthyl group. The method according to claim 1,
The 2-naphthyl group substituted or unsubstituted in the substituents X ₁ to X ₇ is one or two. The method according to claim 1,
Wherein R &lt; ₁ &gt; is substituted with a substituent comprising deuterium or deuterium;
Or an aromatic ring of the aromatic ring of the substituted or unsubstituted 2-naphthyl group is substituted with a substituent including deuterium or deuterium. 6. The method according to any one of claims 1 to 5,
The substituents R ₁ and R ₂ are the same or different and independently of each other represent hydrogen, deuterium, an alkyl group having 1 to 5 carbon atoms; A cycloalkyl group having 3 to 12 carbon atoms; An aryl group having 6 to 10 carbon atoms;
And m and n are 1 or 2, respectively. The method according to claim 1,
The compound represented by the above formula (A) is any one selected from the group consisting of the following compounds [1] to [84]
[Compound 1] [Compound 2] [Compound 3]

[Compound 4] [Compound 5] [Compound 6]

[Compound 7] [Compound 8] [Compound 9]

[Compound 10] [Compound 11] [Compound 12]

[Compound 13] [Compound 14] [Compound 15]

[Compound 16] [Compound 17] [Compound 18]

[Compound 19] [Compound 20] [Compound 21]

[Compound 22] [Compound 23] [Compound 24]

[Compound 25] [Compound 26] [Compound 27]

[Compound 28] [Compound 29] [Compound 30]

[Compound 31] [Compound 32] [Compound 33]

[Compound 34] [Compound 35] [Compound 36]

[Compound 37] [Compound 38] [Compound 39]

[Compound 40] [Compound 41] [Compound 42]

[Compound 43] [Compound 44] [Compound 45]

[Compound 46] [Compound 47] [Compound 48]

[Compound 49] [Compound 50] [Compound 51]

[Compound 52] [Compound 53] [Compound 54]

[Compound 55] [Compound 56] [Compound 57]

[Compound 58] [Compound 59] [Compound 60]

[Compound 61] [Compound 62] [Compound 63]

[Compound 64] [Compound 65] [Compound 66]

[Compound 67] [Compound 68] [Compound 69]

[Compound 70] [Compound 71] [Compound 72]

[Compound 73] [Compound 74] [Compound 75]

[Compound 76] [Compound 77] [Compound 78]

[Compound 79] [Compound 80] [Compound 81]

[Compound 82] [Compound 83] [Compound 84]

A first electrode;
A second electrode facing the first electrode; And
And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises at least one compound selected from the group consisting of the compounds of any one of claims 1 to 5 and 7. 9. The method of claim 8,
Wherein the organic layer comprises at least one of a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a light emitting layer, an electron transporting layer, and an electron injecting layer. 10. The method of claim 9,
Wherein the organic layer interposed between the first electrode and the second electrode is a light emitting layer,
Wherein the light emitting layer comprises a host and a dopant, and the compound is used as a host. 11. The method of claim 10,
Wherein the dopant is a compound represented by the following general formula (1) or (2)
[Chemical Formula 1] &lt; EMI ID =

Among the above-mentioned formulas (1) and (2)
A is a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, an optionally substituted arylene group having 6 to 60 carbon atoms , A substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms having hetero atoms O, N or S;
In the above formula (1)
X ₁ and X ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a single bond, X ₁ and X ₂ may be bonded to each other;
Y ₁ to Y ₂ each independently represent a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 24 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 24 carbon atoms, a cyano group, a halogen group, a substituted or unsubstituted carbon number of 6 A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron, deuterium, or more is selected, Y ₁ to Y ₂ each are the same or different from each other, and can form a condensed ring of aliphatic group, an aromatic, aliphatic or hetero-aromatic heterocyclic group which are adjacent to each other He said;
l and m are each an integer of 1 to 20, and n is an integer of 1 to 4;
In the above formula (2)
C _y is substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, and when b is 2 or more, each cycloalkane may be in fused form. Further, the hydrogen sites in the cycloalkane may be substituted with deuterium or alkyl of 1 to 20 carbon atoms, and are the same or different from each other;
B Is a single bond or - [C (R ₅ ) (R ₆ )] _p -, and p is an integer of 1 to 3; when p is 2 or more, R ₅ and R ₆ are the same or different from each other;
R ₁ , R ₂ , R _3, R ₅ and R ₆ are each independently selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, A substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C6- A substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, Unsubstituted (Substituted or unsubstituted C1-C60 alkyl) amino group, a substituted or unsubstituted C6-C60 arylamino group, a di (substituted or unsubstituted C6- A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms,
a is an integer of 1 to 4, and when a is 2 or more, R ₃ of 2 or more are the same or different, and R ₃ Each R ₃ may be in fused form, and n is an integer from 1 to 4. 10. The method of claim 9,
Wherein at least one layer selected from the respective layers is formed by a deposition process or a solution process. 9. The method of claim 8,
The organic light emitting device includes a flat panel display device; A flexible display device; Monochrome or white flat panel illumination devices; And a device for flexible illumination of a single color or a white color.

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