KR101964677B1 - Pyrene derivatives having substituted groups and organic light-emitting diode including the same - Google Patents

Abstract

[화학식 A] [화학식 B] The present invention relates to a novel compound and an organic electroluminescent device comprising the same as a luminescent material, and more particularly to a novel compound represented by the following formula (A) or (B) and an organic electroluminescent device comprising the novel compound .

[Chemical Formula A]

Description

[0001] The present invention relates to a pyrene derivative compound having a substituent and an organic electroluminescent device including the same,

The present invention relates to a pyrene derivative compound having a substituent group and an organic electroluminescent device comprising the same as a light emitting material. More particularly, the present invention relates to a pyrene derivative compound having a substituent, And an organic electroluminescent device including the same.

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. On the other hand, an organic light emitting diode (OLED), which is a new flat display device, is a display using a self-luminous phenomenon and has a wide viewing angle and can be made thinner and thinner than a liquid crystal display, And 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 electroluminescent device using an organic light emitting phenomenon usually has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic electroluminescent device, the organic material layer may have a multi-layer 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 the organic electroluminescent device, holes are injected into the anode, electrons are injected into the organic layer, and excitons are formed when injected holes and electrons meet. When it falls back to the ground state, the light comes out. Such an organic electroluminescent device is known to have properties 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 electroluminescent 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 can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent 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.

In order for the organic electroluminescent device to sufficiently exhibit the above-described excellent characteristics, materials constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material are supported by a stable and efficient material However, the development of a stable and efficient organic material layer material for an organic electroluminescence device has not been sufficiently developed yet. Therefore, there is a continuing need in the art for the development of new materials.

Accordingly, a first technical object of the present invention is to provide a pyrene derivative compound for an organic electroluminescent device having a long life, a low driving voltage and a high luminous efficiency.

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

In order to achieve the first technical object, the present invention provides a pyrene derivative compound represented by the following formula (A) or (B).

(A)

[Chemical Formula B]

In the above formulas (A) and (B)

The R ₁ To R _4, R ₆ To R < ₉ > are the same or different and each independently represents a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 30 carbon atoms An arylamine group, 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 a hetero atom, O, N or S, A substituted or unsubstituted silane group, a carbonyl group, a phosphoryl group, an amino group, a nitrile group, a hydroxyl group, a nitro group, a halogen group, an amide group and an ester group, May form a condensed ring of aliphatic, aromatic, aliphatic hetero or aromatic hetero with groups adjacent to each other,

R ₅ and R ₁₀ are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted group having 3 to 30 carbon atoms A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted hetero atom having 3 to 50 carbon atoms having O, N or S, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, An aryl group, a substituted or unsubstituted silicon group, and may form a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero with an adjacent group,

Y ₁ to Y ₄ and Y ₆ to Y ₉ are the same or different from each other and each independently selected from the same substituents as defined for R ₁ to R ₄ and R ₆ to R ₉ , Or a substituent represented by the formula [1 '],

Provided that at least one of Y ₄ and Y ₉ is a substituent represented by the following formula 1 or formula 1 '

In Formula B, at least one of Y ₁ to Y ₃ and Y ₆ to Y ₈ is a substituent represented by Structural Formula 1 or Structural Formula 1 'below.

      [Structural formula 1] [Structural formula 1 ']

In the above-mentioned structural formula 1 or structural formula 1 '

The substituent of A, B or C is 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,

When B or C is 2 or more, they are the same or different and form a condensed ring of aliphatic, aromatic, aliphatic hetero or aromatic hetero with groups adjacent to each other,

n is an integer of 1 to 4,

x is an integer of 1 to 4, and y is an integer of 1 to 7.

According to another aspect of the present invention, there is provided an organic electroluminescent device including an anode, a cathode, and a pyrene derivative compound interposed between the anode and the cathode, the pyrene derivative compound being represented by the formula [A] or [B] Lt; / RTI >

According to the present invention, the pyrene derivative compound represented by the formula (A) or (B) has stable and excellent luminescent properties as compared with the existing materials, and thus the organic electroluminescent device including the same can be driven at a low voltage, .

1 is a schematic view of an organic electroluminescent device according to one embodiment of the present invention.

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

In order to unify the terms relating to the substituted part of the pyrene derivative described below, the number of the substitutable part of the hydrogen bonded to the aromatic carbon of the pyrene group in the present invention is defined as follows.

The present invention relates to a pyrene derivative compound contained in a light emitting layer of an organic electroluminescent device, which is a compound represented by the following formula (A) or (B) More specifically, it is as follows.

(A)

[Chemical Formula B]

In the above formulas (A) and (B)

The R ₁ To R _4, R ₆ To R ₉ Are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted C3 to C30 A substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, A substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1-C30 arylthio group, a substituted or unsubstituted C1-C30 alkylamine group, a substituted or unsubstituted C5-C30 arylamine group , 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 hetero atom O, N or S, a substituted or unsubstituted silyl A substituted or unsubstituted silyl group, a carbonyl group, a phosphoryl group, an amino group, a nitrile group, a hydroxyl group, a nitro group, a halogen group, an amide group and an ester group, Aromatic aliphatic, heteroaliphatic, or aromatic hetero ring,

R ₅ and R ₁₀ are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted group having 3 to 30 carbon atoms A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted hetero atom having 3 to 50 carbon atoms having O, N or S, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, An aryl group, a substituted or unsubstituted silicon group, and may form a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero with an adjacent group,

Y ₁ to Y ₄ and Y ₆ to Y ₉ are the same or different from each other and each independently selected from the same substituents as defined for R ₁ to R ₄ and R ₆ to R ₉ , Or a substituent represented by the formula [1 '],

Provided that at least one of Y ₄ and Y ₉ is a substituent represented by the following formula 1 or formula 1 '

In Formula B, at least one of Y ₁ to Y ₃ and Y ₆ to Y ₈ is a substituent represented by Structural Formula 1 or Structural Formula 1 'below.

     [Structural formula 1] [Structural formula 1 ']

In the above-mentioned structural formula 1 or structural formula 1 '

The substituent of A, B or C is 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,

When B or C is 2 or more, they are the same or different and form a condensed ring of aliphatic, aromatic, aliphatic hetero or aromatic hetero with groups adjacent to each other,

n is an integer of 1 to 4,

x is an integer of 1 to 4, and y is an integer of 1 to 7.

In the present invention, the term "substituted or unsubstituted" means a group selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl, alkoxy, alkylamino, arylamino, , Substituted or unsubstituted with one or more substituents selected from the group consisting of an aryloxy group, an aryl group, a heteroaryl group, germanium, phosphorus, boron, hydrogen and deuterium.

More specifically, A in the structural formula 1 or the structural formula 1 'is selected from a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, C represents a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 24 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 24 carbon atoms, a substituted or unsubstituted alkoxy group, 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, boron, a cyano group, a halogen group, a trifluoromethyl group, a deuterium And hydrogen.

More specifically, the B in [structural formula 1] or [structural formula 1 '] may be any one selected from the group consisting of a cyano group, a halogen group, and a trifluoromethyl group.

More specifically, in [Structural Formula 1] or [Structural Formula 1 '], A is selected from 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, and B Is a group selected from the group consisting of a cyano group, a halogen group and a trifluoromethyl group, x is an integer of 1 to 4, and when x is 2 or more, each B may be the same or different from each other, and y may be 0 .

More specifically, in the above formula (A), only one selected from the substituents Y ₄ and Y ₉ is a substituent represented by the above-mentioned [formula 1] or [formula 1 '], and the substituent Y ₁ to Y ₃ and Only one selected from Y ₆ to Y ₈ may be a substituent represented by the above-mentioned [formula 1] or [formula 1 '].

As yet another specific example, the above-mentioned [Chemical Formula A] the substituent Y _4, and Y ₉ is replaced by the [formula 1] or [formula 1 '], respectively, and [Chemical Formula B] In any one selected from the group consisting of Y ₁ to Y ₃ And Y ₆ to Y ₈ may be a substituent represented by the above-mentioned structural formula 1 or [structural formula 1 '].

In the present invention, more specifically, R ₅ and R ₁₀ are the same or different and each independently represents an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, N or S and a heteroaryl group having 4 to 15 carbon atoms.

[Formula 1] or [Formula 1 '] in the pyrene derivative compound according to the above-mentioned [Formula A] or [Formula B] may be any one selected from the group consisting of the following Substituent 1 to Substituent Lt; / RTI >

     [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] [Substituent 53] [Substituent 54]

  [Substituent 55] [Substituent 56] [Substituent 57]

         [Substituent 58] [Substituent 59] [Substituent 60]

       [Substituent group 61] [Substituent group 62] [Substituent group 63]

   [Substituent group 64] [Substituent group 65] [Substituent group 66]

      [Substituent group 67] [Substituent group 68] [Substituent group 69]

      [Substituent group 70] [Substituent group 71] [Substituent group 72]

   [Substituent group 73] [Substituent group 74] [Substituent group 75]

  [Substituent group 76] [Substituent group 77] [Substituent group 78]

    [Substituent group 79] [Substituent group 80] [Substituent group 81]

 [Substituent group 82] [Substituent group 83] [Substituent group 84]

  [Substituent 85] [Substituent 86] [Substituent 87]

  [Substituent group 88] [Substituent group 89] [Substituent group 90]

    [Substituent group 91] [Substituent group 92] [Substituent group 93]

     [Substituent 94] [Substituent 95] [Substituent 96]

When the pyrene derivative compound of the present invention has any one selected from the group consisting of [substituents 1] to [96], the R ₅ And R ₁₀ May be the same or different and each independently selected from a methyl group, an ethyl group, a propyl group, a butyl group, a cyclopentyl group, a cyclohexyl group and a phenyl group.

Hereinafter, a method of producing the pyrene-based derivative of the present invention will be briefly described.

The compound of formula (A) of the present invention can be prepared by the following Reaction Scheme 1 and Reaction Scheme 2.

[Reaction Scheme 1]

(중간체A)

(Intermediate A)

[Reaction Scheme 2]

[화학식 A] (Intermediate A) + secondary amine

(A)

The secondary amine reacting with the intermediate A is a secondary amine in the form of hydrogen bonded to the substituent of the formula 1 defined in the formula (A) of the present invention.

Therefore, the compound of formula (A) of the present invention contains at least one tertiary amine having at least one substituent of the structural formula (1) or (1 ') by substituting at least one of halogen at positions 4 and 9 of pyrene with a secondary amine Lt; RTI ID = 0.0 > pyrene < / RTI >

Further, the compound of formula (A) of the present invention may have a substituent other than hydrogen or deuterium at positions 5 and 10 of pyrene, and when two phenyl groups of the biphenyl compound precursor of the intermediate A contain a substituent, Can be substituted with a substituent other than hydrogen.

If the substituent substituted on two phenyl groups of the biphenyl compound as a precursor of the intermediate A is halogen, the compound of formula (A) may have three or more amine groups of the formula (1).

Meanwhile, the compound of formula (B) of the present invention can be prepared through the following reaction formula (3) and (4).

[Reaction Scheme 3]

(중간체B)

(Intermediate B)

[Reaction Scheme 4]

[화학식 B] (Intermediate B) + Secondary amine

[Chemical Formula B]

The secondary amine reacting with the intermediate B is a secondary amine in the form of a hydrogen-bonded substituent of the formula 1 defined in formula (B) of the present invention.

Therefore, the compound of formula (B) of the present invention may have a substituent other than hydrogen or deuterium at positions 5 and 10 of pyrene, and two phenyl groups of the biphenyl compound, which is a precursor of intermediate B, A tertiary amine having at least one substituent of the structural formula 1 or the structural formula 1 'can be obtained by substituting at least one of the positions 1 to 3 or 6 to 8 of the pyrene with the secondary amine of the structural formula 1 or 1' Can be provided.

Further, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and a pyrene derivative compound interposed between the anode and the cathode, and represented by the formula (A) or (B).

In this case, the layer containing the novel compound is preferably a light emitting layer between the anode and the cathode, and a hole injecting layer, a hole transporting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer and an electron injecting layer And at least one layer selected from the group consisting of

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, A display element, a display element, or a monochromatic or white illumination element.

Also, 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 further include various phosphorescent host materials.

As a specific example, a hole transport layer (HTL) may be further stacked, and an electron transport layer (ETL) may be further stacked between the cathode and the organic emission layer. An electron donor molecule having a low ionization potential is used as the material of the hole transport layer. A diamine, triamine or tetraamine derivative having a basic skeleton of triphenylamine is used as the material of the hole transport layer. It is 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 electroluminescent device according to the present invention can transport electrons supplied from the cathode smoothly to the organic luminescent layer and inhibit the movement of holes which are not bonded in the organic luminescent layer, .

The material 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 can 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.

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

1 is a cross-sectional view showing the structure of an organic electroluminescent device of the present invention. The organic electroluminescent device according to the present invention includes an anode 20, a hole transport layer 40, an organic emission layer 50, an electron transport layer 60 and a cathode 80, The electron injecting 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.

The organic electroluminescent device of the present invention and its manufacturing method will be described with reference to FIG. 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.

According to another embodiment of 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 is formed by a single molecular deposition method or a solution process And the organic electroluminescent device according to the present invention can be used for a display device, a display device, and a monochromatic or white illumination device.

The light emitting layer may further include a host, and the compound of the present invention contained in the light emitting layer may serve as a dopant.

Also, 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 further include various phosphorescent host materials.

At this time, the host may be an anthracene-based compound represented by the following general formula (1).

≪ Formula 1 >

In Formula 1,

The Ar ₁₁ And Ar ₁₂ independently represent a substituted or unsubstituted arylene group having 5 to 60 carbon atoms;

Ar ₁₃ and Ar ₁₄ are, independently of each other, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 5 to 60 carbon atoms;

e and f are independently of each other an integer of 0 to 5;

For example, in the general formula (1), Ar ₁₁ and Ar ₁₂ represent a phenylene group; Or a phenylene group substituted with at least one of a phenyl group, a naphthyl group and an anthryl group, but is not limited thereto.

In Formula 1, e and f may be, independently of each other, 0, 1 or 2.

Wherein Ar ₁₃ and Ar ₁₄ are each independently a C ₁ -C ₁₀ alkyl group substituted by at least one of a phenyl group, a naphthyl group and an anthryl group; A phenyl group; Naphthyl group; Anthryl group; Pyrenyl; A phenanthrenyl group; And heavy hydrogen, 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 salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₆₀ alkyl, C A phenyl group substituted with at least one of a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group, a naphthyl group, an anthryl group, a pyrenyl group and a phenanthrenyl group; But is not limited thereto.

For example, in the general formula (1), Ar ₁₁ and Ar ₁₂ represent a phenylene group; Or a phenylene group substituted by at least one of a phenyl group, a naphthyl group and an anthryl group; e and f are, independently of each other, 0, 1 or 2; Ar ₁₃ and Ar ₁₄ are each independently a C ₁ -C ₁₀ alkyl group substituted by at least one of a phenyl group, a naphthyl group and an anthryl group; A phenyl group; Naphthyl group; Anthryl group; Pyrenyl; And a phenanthrenyl group; But is not limited thereto.

In the present specification, specific examples of the unsubstituted alkyl group having 1 to 60 carbon atoms include a linear or branched alkyl group having 1 to 60 carbon atoms such as methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isoamyl, And the substituted alkyl group having 1 to 60 carbon atoms is a group in which at least one hydrogen atom of the unsubstituted C ₁ -C ₆₀ alkyl group is substituted with a substituent selected from the group consisting of deuterium, a halogen atom, a hydroxy group, a nitro group, a cyano group, an amino group, an amidino group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, or an alkyl group having 1 to 60 carbon atoms, an alkenyl group having 2 to 60 carbon atoms, an alkynyl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, of 2 to 60 heteroaryl _{group, -N (Q 11) (Q} 12), and _{-Si (Q 13) (Q 14} ) (Q 15) ( wherein, Q ₁₁ to Q ₁₅ are independently H, C 1 to each other An alkyl group having 1 to 60 carbon atoms, an alkenyl group having 2 to 60 carbon atoms, An alkynyl group having a number of 2 to 60, an aryl group having a carbon number of 6 to 60, and a heteroaryl group having a carbon number of 2 to 60).

The unsubstituted alkoxy group having 1 to 60 carbon atoms in the present specification has a formula of -OA (wherein A is an unsubstituted alkyl group having 1 to 60 carbon atoms as described above), and specific examples thereof include methoxy, ethoxy , And isopropyloxy. At least one of the hydrogen atoms of these alkoxy groups may be substituted with the same substituents as those of the substituted C ₁ -C ₆₀ alkyl group described above.

In the present specification, an unsubstituted alkylthio group having 1 to 60 carbon atoms (or a C ₁ -C ₆₀ alkylthio group) is -S (wherein A is an unsubstituted alkyl group having 1 to 60 carbon atoms as described above) And at least one hydrogen atom of these alkoxy groups may be substituted with the same substituents as those of the substituted alkyl group having 1 to 60 carbon atoms described above.

In the present specification, an unsubstituted alkenyl group having 21 to 60 carbon atoms (or a C ₂ -C ₆₀ alkenyl group) contains one or more carbon double bonds at the middle or end of the unsubstituted alkyl group having 2 to 60 carbon atoms it means. Examples include ethenyl, propenyl, butenyl, and the like. At least one hydrogen atom of these unsubstituted alkenyl groups having 2 to 60 carbon atoms can be substituted with the same substituents as those of the substituted alkyl group having 1 to 60 carbon atoms.

In the present specification, an unsubstituted alkynyl group having 2 to 60 carbon atoms (or a C ₂ -C ₆₀ alkynyl group) has at least one carbon triple bond at the middle or end of an alkyl group having 2 to 60 carbon atoms as defined above . Examples include ethynyl, propynyl, and the like. At least one hydrogen atom of these alkynyl groups may be substituted with the same substituents as those of the substituted alkyl group having 1 to 60 carbon atoms described above.

In the present specification, an unsubstituted aryl group having 6 to 60 carbon atoms means a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms including at least one aromatic ring, An arylene group of 60 means a divalent group having from 6 to 60 carbon atoms carbocyclic aromatic systems containing at least one aromatic ring. When the aryl group and the arylene group include two or more rings, the two or more rings may be fused to each other. At least one of the hydrogen atoms of the aryl group and the arylene group may be substituted with the same substituents as those of the substituted alkyl group having 1 to 60 carbon atoms described above.

Examples of the substituted or unsubstituted aryl group having 6 to 60 carbon atoms include a phenyl group, an alkylphenyl group having 1 to 10 carbon atoms (e.g., ethylphenyl group), an alkylbiphenyl group having 1 to 10 carbon atoms (e.g., ethylbiphenyl O-, m- and p-tolyl groups, o-, m- and p-fluorophenyl groups, dichlorophenyl groups), dicyanophenyl groups, trifluoromethoxyphenyl groups, (N, N'-dimethyl) aminophenyl group, (N, N'-diphenyl) aminophenyl group, pentaerythrityl group, p-cumene group, mesityl group, phenoxyphenyl group, (For example, methyl naphthyl group), a C ₁ -C ₁₀ alkoxynaphthyl group (for example, methylthio group, ethylthio group, naphthyl group, naphthyl group, For example, a methoxynaphthyl group), an anthracenyl group, an azenyl group, an heptalenyl group, an acenaphthylenyl group, a phenarenyl group, a fluorenyl group, an anthraquinolyl group, A phenanthryl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, an ethyl-chrysenyl group, a picenyl group, a perylenyl group, a chloroperylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group, Examples of the substituted aryl group having 6 to 60 carbon atoms include a phenyl group, a hexacenyl group, a rubicenyl group, a coronenyl group, a trinaphthylanyl group, a heptaphenyl group, a heptacenyl group, a pyranthrenyl group and an obarenyl group. Can be easily recognized by referring to the unsubstituted examples of the aryl group having 1 to 60 carbon atoms and the substituent of the substituted alkyl group having 1 to 60 carbon atoms as described above. Examples of the substituted or unsubstituted C6-C60 arylene group can be easily recognized with reference to the substituted or unsubstituted C6-C60 aryl group.

In the present specification, the unsubstituted heteroaryl group having 2 to 60 carbon atoms means a monovalent group having a system consisting of at least one aromatic ring having at least one hetero atom selected from N, O, P or S and the remaining ring atoms being C And the unsubstituted heteroarylene group having 2 to 60 carbon atoms means a divalent group having a system consisting of at least one aromatic ring having at least one hetero atom selected from N, O, P or S and the remaining ring atoms being C do. Herein, when the heteroaryl group and the heteroarylene group include two or more rings, two or more rings may be fused with each other. At least one hydrogen atom of the heteroaryl group and the heteroarylene group may be substituted with the same substituent as in the case of the alkyl group having 1 to 60 carbon atoms described above.

Examples of the unsubstituted heteroaryl group having 2 to 60 carbon atoms include a pyrazolyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridinyl group, An imidazopyrimidinyl group, an imidazopyrimidinyl group, and the like can be given as examples of the pyrimidinyl group, the pyrimidinyl group, the pyrimidinyl group, the triazinyl group, the carbazolyl group, the indolyl group, the quinolinyl group, the isoquinolinyl group, Examples of the unsubstituted heteroarylene group having 2 to 60 carbon atoms can be easily recognized with reference to the substituted or unsubstituted examples of the substituted or unsubstituted arylene group having 2 to 60 carbon atoms.

The substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms is -OA ₂ (wherein A ₂ is the substituted or unsubstituted aryl group having 5 to 60 carbon atoms), and the substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms aryl Im coming refers to -SA ₃ (herein, a ₃ is an aryl group having a carbon number of 5 to 60 ring wherein the substituted or unsubstituted).

The light emitting layer may further include at least one compound selected from compounds represented by the following formulas BH1 to BH44, but is not limited thereto.

     BH01 BH02 BH03 BH04

     BH05 BH06 BH07 BH08

   BH09 BH10 BH11 BH12

    BH13 BH14 BH15 BH16

BH17 BH18 BH19 BH20

BH21 BH22 BH23 BH24

BH21 BH22 BH23 BH24

    BH25 BH26 BH27 BH28

      BH29 BH30 BH31 BH32

   BH33 BH34 BH35 BH36

     BH37 BH38 BH39 BH40

       BH41 BH42 BH43 BH44

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 Compound BD1

1. Synthesis of dihalopyrene intermediate

(1-A) Synthesis of 4,9-diiodo-5,10-diphenyl-pyrene (hereinafter referred to as "pyrene A")

(1-A-1) Synthesis of 2-bromobiphenylacetylene

[Reaction Scheme 5]

To a solution of 2-bromo-iodo-benzene (10 g, 35 mmol), Pd (PPh3) 4 (0.8 g, 0.5 mmol) and CuI (0.54 g, 1 mmol) in 50 mL of triethylamine was stirred at room temperature (Reaction proceeded in nitrogen atmosphere) and phenylacetylene (3.6 mL, 35 mmol) was slowly added.

After stirring for about 1 hour at room temperature, 300 mL of hexane was added to terminate the reaction. The whole solution was passed through silica gel to separate the product, and the column was further drained with 500 mL of hexane. The solvent was removed to give a white product (yield: 98%).

* 128MS (MALDI-TOF): m / z 257 [M] ⁺

(1-A-2) Synthesis of 2-biphenylacetyleneboronic acid

[Reaction Scheme 6]

2-Bromobiphenylacetylene (10 g, 55 mmol) was dissolved in 100 mL of THF. The n-BuLi (50 mL) was added slowly while cooling to -78 ° C. After the addition, trimethylborate (6.57 g, 63 mmol) was added at -78 ° C for about 1 hour. After stirring at -78 ° C for 1 hour, the mixture was stirred at room temperature for 2 hours, and 2N HCl was added to adjust the acidity. After the extraction with EA, the solvent was removed, and the solution was diluted with hexane and stirred at -78 ° C to solidify to obtain a white solid. (70% yield)

MS (MALDI-TOF): m / z 223 [M] ^&lt; ^{+ &}

(1-A-3) Synthesis of 2,2'-diphenylethynylbiphenyl

[Reaction Scheme 7]

(9.5 g, 43 mmol), K2CO3 (10.75 g, 78 mmol) and Pd (PPh3) 4 (0.9 g, 1 mmol) were added to a solution of 2-bromobiphenylacetylene (10 g, 55 mmol) Was added to a mixed solution of 100 mL of toluene, 100 mL of THF, and 50 mL of H2O and refluxed. After the reaction was completed, the organic solvent was removed by layer separation, and the product was separated by column separation (MC: Hx = 1: 9) (yield 70%).

MS (MALDI-TOF): m / z 355 [M] ^&lt; ^{+ &}

(1-A-4) Synthesis of pyrene A

[Reaction Scheme 8]

                                     Pyrenean A

2,2'-diphenylethynylbiphenyl (10 g, 28 mmol) was dissolved in 100 mL of MC. 68 mL of ICl (1M in MC) was slowly added at room temperature. After stirring at room temperature for 1 hour, iodine was removed with saturated Na2S2O3 and extracted with EA. The product was isolated by column (MC: Hx = 1: 9) (yield 60%).

MS (MALDI-TOF): m / z 606 [M] ^&lt; ^{+ &}

(1-B) Synthesis of 2,7-dibromo-5,10-diphenyl-pyrene (hereinafter referred to as "pyrene B")

(1-B-1) Synthesis of 4,4'-dibromo-2,2'-dinitro-biphenyl.

[Reaction Scheme 9]

250 g (0.890 mol) of 2,5-dibromonitrobenzene, 135.74 g (2.136 mol) of copper powder and 1 L of DMF were placed. The temperature of the reactor was raised to 125 캜 and stirred for 3 hours. When the reaction was completed, the temperature was lowered to room temperature, 500 mL of toluene was added, and the mixture was stirred. The insoluble inorganic salts were removed by celite filtration and the filtrate was dried. To the dried filtrate, 2 L of methanol was added and stirred vigorously. The resulting crystals were filtered and dissolved again in 500 mL of toluene. The remaining inorganic salt was removed by celite filtering, and the filtrate was dried. MeOH was added thereto and stirred vigorously to obtain 139 g (yield 77.7%) of 4,4'-dibromo-2,2'-dinitro- &Lt; / RTI &gt;

MS (MALDI-TOF): m / z 401 [M] ^&lt; ^{+ &}

(1-B-2) Synthesis of 4,4'-dibromo-2,2'-diaminobiphenyl

[Reaction Scheme 10]

139.7 g (0.347 mol) of 4,4'-dibromo-2,2'-dinitro-biphenyl was added and 2 L of ethanol was added. Then 1 L of 12 M HCl was added and stirred. The temperature of the reactor was lowered to 0 ° C and 165 g (1.39 mol) of Tin powder was added slowly over 20 minutes. The temperature of the reactor was raised to 100 ° C and refluxed for 3 hours. When the reaction was completed, the temperature of the reactor was lowered to 0 ° C. and 12 M 1 L of sodium hydroxide aqueous solution was slowly added to make the reaction solution basic. Ethylacetate was added to extract the organic layer, and the organic layer was dried and concentrated. Hexane and methylene chloride were used as a developing solvent to separate 4,4'-dibromo-2,2'-diaminobiphenyl (87.7 g, yield 73.8%) by column chromatography.

MS (MALDI-TOF): m / z 341 [M] ^&lt; ^{+ &}

(1-B-3) Synthesis of 4,4'-dibromo-2,2'-diiodobiphenyl

[Reaction Scheme 11]

87.7 g (0.256 mol) of 4,4'-dibromo-2,2'-diaminobiphenyl, 380 mL of 12 M HCl, and 380 mL of water. The temperature of the reactor was lowered to 0 ° C. Sodium nitrite (44.2 g, 0.641 mol) was dissolved in 220 mL of water and slowly added dropwise to the reactor. When the dropwise addition was completed, the mixture was stirred at the same temperature for 1 hour. Potassium iodide was dissolved in 850 mL of water and slowly added dropwise. When the dropwise addition was completed, the solution was stirred at room temperature for 1 hour. The temperature of the reactor was raised to 60 DEG C and stirred for 3 hours. When the reaction was complete, the mixture was cooled to room temperature and extracted with Ethylacetate to separate the organic layer. The separated organic layer was dried over anhydrous, dried and then subjected to column chromatography using hexane as a developing solvent to obtain 42.1 g (yield: 29.1%) of 4,4'-dibromo-2,2'-diiodobiphenyl.

MS (MALDI-TOF): m / z 563 [M] ^&lt; ^{+ &}

(1-B-4) Synthesis of 4,4'-dibromo-2,2'-diphenylethynylbiphenyl

[Reaction Scheme 12]

(0.036 mol) of 4,4'-dibromo-2,2'-diiodobiphenyl and 0.7 g (0.0035 mol) of copper iodide and 1.6 g (0.0014 mol) of Pd (PPh3) 4 in a 500 mL round- mol) was dissolved in 200 mL of triethyl amine. 9.3 g (0.085 mol) of phenylacetylene was slowly added dropwise to the reactor and stirred for 1 hour. After the reaction was completed, it was dissolved in MC and filtered using Celite and Silica. The filtrate was dried, and 13.5 g (yield 74.3%) of 4,4'-dibromo-2,2'-diphenylethynylbiphenyl obtained by column chromatography using hexane as a developing solvent was obtained.

MS (MALDI-TOF): m / z 511 [M] ^&lt; ^{+ &}

(1-B-5) Synthesis of pyrene B

[Reaction Scheme 13]

                                             Pyrene B

A 250 mL reactor was charged with 12.3 g (0.024 mol) of 4,4'-dibromo-2,2'-diphenylethynylbiphenyl in a nitrogen stream and dissolved in 120 mL of dichloroethane. Iron (III) trifluoro-methanesulfonate (1.2 g, 0.002 mol) was added and refluxed for 12 hours. After completion of the reaction, the mixture was hot-filtered. The filtrate was dried and EA slurried. The resulting solid was filtered and recrystallized to obtain 2.0 g (yield: 16.3%) of 5,10-dibromo-2,7-diphenyl-pyrene.

MS (MALDI-TOF): m / z 511 [M] ^&lt; ^{+ &}

2. Synthesis of amine derivatives

Amine derivative 1: Synthesis of 3- (naphthalen-1-yl) -5- (phenylamino) benzonitrile

Synthesis Example 2- (1): Synthesis of 3-bromo-5- (naphthalen-1-yl) benzonitrile

To a round bottom flask was added 3,5-dibromo-benzonitrile 20.0 g (77 mmol) and 1-naphthalene boronic acid 13.2 g (77 mmol), tetrakis (triphenylphosphine) palladium _{{Pd (PPh 3) 4}} 1.8g ( (153 mmol) of potassium carbonate, 30 mL of water, 100 mL of toluene and 100 mL of tetrahydrofuran, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction product was separated, and the organic layer was concentrated under reduced pressure. The organic layer was recrystallized from hexane and dried to obtain 13.1 g of a white solid having a yield of 55.5%.

Synthesis Example 2- (2): Synthesis of 3- (naphthalen-1-yl) -5- (phenylamino) benzonitrile

13.1 g (43 mmol) of 3-bromo-5- (naphthalen-1-yl) benzonitrile prepared in the above Synthesis Example 2- (1), 3.6 g (43 mmol) of aniline, 0.14 g (0.6 mmol) of 2,2-bisdiphenylphosphino-1,1'-binaphthyl, 8.2 g (0.6 mmol) of sodium tertiary butoxide and 130 ml of toluene were added, Lt; / RTI &gt; After the temperature was lowered, the organic layer was concentrated and separated by column chromatography. Recrystallization from dichloromethane and hexane followed by filtration and drying gave 7.9 g of a white solid with a yield of 58%.

3. Synthesis of pyrene derivative compound BD1 containing a substituent

The 3- (1-yl) prepared in Preparation Example 2- (2) To a round bottom flask was added 5- (phenylamino) benzonitrile 7.9 g (25 mmol), the pyrene A 6.1 g (10mmol), palladium Acetate (Pd (OAc) ₂ ), 3.95 g (41 mmol) of sodium tertiary butoxide, 0.08 g (0.4 mmol) of triturated butylphosphine and 80 ml of toluene, Lt; / RTI &gt; for 2 hours. When the reaction was completed, the temperature was lowered to room temperature. When crystals were formed, the crystals were filtered and then recrystallized with toluene and ethanol. The resultant solid was filtered and dried to obtain 1.8 g (yield: 18.2%) of pale yellow solid compound BD1.

MS (MALDI-TOF): m / z 991 [M] ^&lt; ⁺ & gt ^;

Synthesis Example 2. Synthesis of Compound BD2

Dibromo-1-fluorobenzene was used instead of 3,5-dibromobenzonitrile in Synthesis Example 2- (1), 2.2 g of the title compound was obtained in a yield of 22.5% A pale yellow solid compound BD2 was obtained.

MS (MALDI-TOF): m / z 977 [M] ^&lt; ^{+ &}

Synthesis Example 3. Synthesis of Compound BD3

In the same manner as in Synthesis Example 2- (1) except that 4-bromo-2-fluoroaniline was used in place of 3,5-dibromobenzonitrile and 2-naphthalene boronic acid was used instead of 1- 2), bromo benzene was used instead of aniline, to obtain 2 g of a pale yellow solid compound BD3 having a yield of 20.5%.

MS (MALDI-TOF): m / z 977 [M] ^&lt; ^{+ &}

Synthesis Example 4. Synthesis of compound BD4

Except that 3,5-dibromo-1-fluorobenzene was used instead of 3,5-dibromobenzonitrile in Synthesis Example 2- (1), and p-toluidine was used in place of aniline in Synthesis Example 2- (2) , The same procedure was followed to obtain 2.2 g of a pale yellow solid compound BD4 having a yield of 22%.

MS (MALDI-TOF): m / z 1005 [M] ^&lt; ⁺ & gt ^;

Synthesis Example 5. Synthesis of Compound BD5

Dibromo-1-fluorobenzene instead of 3,5-dibromobenzonitrile and 2-naphthaleneboronic acid instead of 1-naphthaleneboronic acid in Synthesis Example 2- (1) In the same manner as in 2- (2) except that 4-tert-butylaniline was used instead of aniline, 1.9 g (yield: 17.4%) of a pale yellow solid compound BD5 was obtained.

MS (MALDI-TOF): m / z 1090 [M] ^&lt; ^{+ &}

Synthesis Example 6. Synthesis of Compound BD6

Bromo-5- (trifluoromethyl) aniline was used in place of 3,5-dibromobenzonitrile in Synthesis Example 2- (1) and bromo-5- (trifluoromethyl) aniline was used in place of aniline, Benzene was used to synthesize 2.5 g of a pale yellow solid compound BD6 having a yield of 23.2%.

MS (MALDI-TOF): m / z 1078 [M] ^&lt; ^{+ &}

Synthesis Example 7: Synthesis of compound BD7

Dihalopyrane intermediate was replaced with 2,4-dibromo-6-fluoroaniline in place of 3,5-dibromobenzonitrile in Synthesis Example 2- (1), phenyl- d5-boronic acid and that bromobenzene-d5 was used instead of aniline in Synthesis Example 2- (2), 1.9 g and a pale yellow solid compound BD7 having a yield of 17.9% were obtained.

MS (MALDI-TOF): m / z 1060 [M] ^&lt; ^{+ &}

Synthesis Example 8. Synthesis of Compound BD8

Dihalopyrane intermediate was replaced with 2,4-dibromo-6-fluoroaniline in place of 3,5-dibromobenzonitrile in Synthesis Example 2- (1), phenyl- d5-boronic acid was used and that 4-bromobenzonitrile was used in place of aniline in Synthesis Example 2- (2), to obtain 2.08 g of a pale yellow solid compound BD8 having a yield of 18.2%.

MS (MALDI-TOF): m / z 1100 [M] ⁺

Synthesis Example 9. Synthesis of compound BD9

Dibromo-1-nitrobenzene instead of 2,5-dibromonitrobenzene in Scheme 9 was synthesized in the same manner as in Schemes 9 to 13 to give 1,6-dibromo-5,10-di Phenyl-pyrene (yield: 16.3%).

 Dibromo-5,10-diphenyl-pyrene in place of 3,5-dibromobenzonitrile in Synthesis Example 2- (1) and 2,4-dibromo-6-fluoroaniline , Except that phenyl-d5-boronic acid was used in place of 1-naphthaleneboronic acid, and 4-bromobenzonitrile was used in place of aniline in Synthesis Example 2- (2) to obtain 1.8 g (yield: 16.4% To give a pale yellow solid compound BD9.

MS (MALDI-TOF): m / z 1100 [M] ⁺

Examples 2 to 9

The ITO glass was patterned to have a light emitting area of 2 mm 2 mm and then cleaned. After the ITO glass was mounted in a vacuum chamber, the base pressure was adjusted to 1 × 10 ^-7 torr, and CuPc (800 Å) and α-NPD (300 Å) were sequentially formed on the ITO. a film forming (250 Å) and then by film-forming in the order of _{Alq 3 (350Å), LiF (} 5 Å), Al (500 Å) was prepared in an organic electroluminescent device.

Comparative Example

The light emitting layer further contains a pyrene compound represented by the following formula (2) as a guest compound, and a compound represented by the formula (3) or (4) is used as a host material.

       [Chemical Formula 2] &lt; EMI ID =

Evaluation example

Current density, luminance, color coordinates, and lifetime were measured for the organic electroluminescent devices manufactured according to Examples 2, 3, 4, 7 and 8 and Comparative Examples 1 and 2, and the results are shown in Table 1 ]. T97 means the time required for the luminance to be reduced to 97% of the initial luminance.

Voltage Current density (mA / cm 2) Brightness (Cd / m2) CIEx CIEy T97 Example 2
3.9 10 700 0.14 0.10 175 Example 3
4.0 10 690 0.14 0.10 148 Example 4
4.0 10 650 0.14 0.10 160 Example 7
3.9 10 780 0.14 0.11 196 Example 8
3.9 10 750 0.14 0.12 188 Example 9
3.9 10 740 0.14 0.12 192 Comparative Example 1
5.1 10 560 0.14 0.17 20 Comparative Example 2
6.2 10 250 0.14 0.15 15

As shown in Table 1, the organic electroluminescent device including the organic electroluminescent compound according to the present invention has low driving voltage and is excellent in light emission characteristics such as brightness and lifetime, and thus 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 (14)

A pyrene-based derivative represented by the following formula [A] or [B]
(A)

[Chemical Formula B]

In the above formulas (A) and (B)
Wherein R ₁ to R ₄ and R ₆ to R ₉ are the same or different and each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 A substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a nitrile group, a nitro group, and a halogen group, and may form an aliphatic or aromatic condensed ring with the adjacent groups,
R ₅ and R ₁₀ are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted group having 5 to 50 carbon atoms An aryl group, an aliphatic or aromatic condensed ring with an adjacent group,
Y ₁ to Y ₄ and Y ₆ to Y ₉ are the same or different from each other and each independently selected from the same substituents as defined for R ₁ to R ₄ and R ₆ to R ₉ , Or a substituent represented by the formula [1 '],
Provided that only one selected from the substituents Y ₄ and Y ₉ is a substituent represented by the above-mentioned [formula 1] or [formula 1 '],
In the formula (B), only one selected from the substituents Y ₁ to Y ₃ and Y ₆ to Y ₈ is a substituent represented by the above-mentioned [formula 1] or [formula 1 '];
Alternatively, in the above-mentioned formula (A), the substituents Y ₄ and Y ₉ are respectively substituted by the above-mentioned [formula 1] or [formula 1 '
In the formula (B), any one selected from Y ₁ to Y ₃ and Y ₆ to Y ₈ are each a substituent represented by the above-mentioned [formula 1] or [formula 1 '];
[Structural formula 1] [Structural formula 1 ']

In the above-mentioned structural formula 1 or structural formula 1 '
The substituent of A or C is a substituted or unsubstituted aryl group having 6 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 halogen atom, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, deuterium, and hydrogen. More than species are selected,
Wherein B is any one selected from the group consisting of a cyano group, a halogen group, and a trifluoromethyl group,
When B or C is 2 or more, they are the same or different and form an aliphatic or aromatic condensation ring with the adjacent groups,
n is an integer of 1 to 4,
x is an integer of 1 to 4, y is an integer of 1 to 7,
The 'substituted' in the 'substituted or unsubstituted' means substituted by one or more substituents selected from the group consisting of deuterium, cyano, halogen, nitro, alkyl, alkoxy and aryl. The method according to claim 1,
A in the above Structural Formula 1 or Formula 1 'is a substituted or unsubstituted aryl group having 6 to 24 carbon atoms,
C is a substituted or unsubstituted C 1 -C 24 alkyl group, a substituted or unsubstituted C 3 -C 24 cycloalkyl group, a substituted or unsubstituted C 1 -C 40 alkylsilyl group, a substituted or unsubstituted C 6 -C 30 An arylsilyl group, a cyano group, a halogen group, deuterium, and hydrogen. delete delete delete delete The method according to claim 1,
Wherein R ₅ and R ₁₀ are the same as or different from each other and each independently selected from an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and an aryl group having 6 to 15 carbon atoms. 8. The method of claim 7,
[Formula 1] or [Formula 1 '] in Formula (A) or Formula (B)
Is any one selected from the group consisting of the following [substituent groups 1] to [substituent group 84]
[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] [Substituent 53] [Substituent 54]

[Substituent 55] [Substituent 56] [Substituent 57]

[Substituent 58] [Substituent 59] [Substituent 60]

[Substituent group 61] [Substituent group 62] [Substituent group 63]

[Substituent group 64] [Substituent group 65] [Substituent group 66]

[Substituent group 67] [Substituent group 68] [Substituent group 69]

[Substituent group 70] [Substituent group 71] [Substituent group 72]

[Substituent group 73] [Substituent group 74] [Substituent group 75]

[Substituent group 76] [Substituent group 77] [Substituent group 78]

[Substituent group 79] [Substituent group 80] [Substituent group 81]

[Substituent group 82] [Substituent group 83] [Substituent group 84]

The method according to claim 1,
Wherein R ₅ and R ₁₀ are the same or different from each other and each independently selected from a methyl group, an ethyl group, a propyl group, a butyl group, a cyclopentyl group, a cyclohexyl group, and a phenyl group. Anode;
Cathode; And
An organic electroluminescent element interposed between the anode and the cathode, the organic electroluminescent element comprising a compound according to any one of claims 1, 2, 7 to 9. 11. The method of claim 10,
Wherein the compound is contained in the light emitting layer between the anode and the cathode. 12. The method of claim 11,
Wherein at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer and an electron injecting layer is further interposed between the anode and the cathode. 13. The method of claim 12,
Wherein at least one layer selected from the group consisting of 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 molecular deposition method or a solution process. 11. The method of claim 10,
Wherein the organic electroluminescent device is used in a display device, a display device, or a device for monochromatic or white illumination.

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