KR102002020B1 - Pyrene derivatives having substituted cyclic amine 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

FIELD OF THE INVENTION The present invention relates to a pyrene derivative compound having a cyclic amine substituent and an organic electroluminescent device including the cyclic amine substituent,

The present invention relates to a pyrene derivative compound having a cyclic amine substituent and an organic electroluminescent device including the same as a luminescent material. More particularly, the present invention relates to a pyrene derivative compound having a cyclic amine substituent and a luminescent property To a pyrene derivative compound having a stable cyclic amine 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 having a cyclic amine substituent represented by the following formula (A) or (B).

(A)

[Chemical Formula B]

In the above formulas (A) and (B)

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 alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted group having 2 to 30 carbon atoms 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 carbon number 6 A substituted or unsubstituted aryloxy group having 1 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, Or an unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a heteroaryl group having 3 to 50 carbon atoms having a substituted or unsubstituted heteroatom, O, N or S A substituted or unsubstituted aryl group, 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 And 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 , May have a substituent represented by the formula

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

In the formula (B), at least one of Y ₁ to Y ₃ and Y ₆ to Y ₈ is a substituent represented by the following formula (1).

[Structural formula 1]

In the above structural formula 1,

Cy is a substituted or unsubstituted cycloalkane having 3 to 8 carbon atoms, m is an integer of 1 to 4, and when m is 2 or more, each cycloalkane may be fused. The substituted hydrogen may be substituted with deuterium or alkyl, and may be the same or different from each other.

X ₂ is a single bond or - [C (R ₁₅ ) (R ₁₆ )] n-, n is an integer of 1 to 3, and when n is 2 or more, R ₁₅ and R ₁₆ are the same or different from each other ;

L ₁ represents a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylene group having 2 to 60 carbon atoms A substituted or unsubstituted C2-C60 alkynylene group, a substituted or unsubstituted C3-C60 cycloalkylene group, a substituted or unsubstituted C2-C60 heterocycloalkylene group, a substituted or unsubstituted C2-C60 alkynylene group, A substituted or unsubstituted arylene group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;

R ₁₁ , R ₁₂ , R _13, R ₁₅ and R ₁₆ independently represent hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a 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, Unsuitable (Alkyl) amino group having 1 to 60 carbon atoms, di (alkyl having 1 to 60 carbon atoms), di (substituted or unsubstituted aryl) amino group having 6 to 60 carbon atoms, di (substituted or unsubstituted) 6 to 60 aryl) amino groups;

is a case of being an integer of 1 to 4, a is 2 or more at least two R ₁₃ are the same or different, R ₁₃ to each other with a plurality, each R ₁₃ may be been fused form.

* Is a bonding site with the pyrene group in the above-mentioned [A] or [B].

According to another aspect of the present invention,

A first electrode, a second electrode facing the first electrode, and an organic layer sandwiched between the first electrode and the second electrode, wherein the organic layer is a pyrene derivative represented by the formula (A) or (B) An organic light emitting device comprising at least one compound.

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)

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 alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted group having 2 to 30 carbon atoms 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 carbon number 6 A substituted or unsubstituted aryloxy group having 1 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, Or an unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a heteroaryl group having 3 to 50 carbon atoms having a substituted or unsubstituted heteroatom, O, N or S A substituted or unsubstituted aryl group, 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 And 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 , May have a substituent represented by the formula

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

In the formula (B), at least one of Y ₁ to Y ₃ and Y ₆ to Y ₈ is a substituent represented by the following structural formula (1).

[Structural formula 1]

In the above structural formula 1,

Cy is a substituted or unsubstituted cycloalkane having 3 to 8 carbon atoms, m is an integer of 1 to 4, and when m is 2 or more, each cycloalkane may be fused. The substituted hydrogen may be substituted with deuterium or alkyl, and may be the same or different from each other.

X ₂ is a single bond or - [C (R ₁₅ ) (R ₁₆ )] n-, n is an integer of 1 to 3, and when n is 2 or more, R ₁₅ and R ₁₆ are the same or different from each other ;

L ₁ represents a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylene group having 2 to 60 carbon atoms A substituted or unsubstituted C2-C60 alkynylene group, a substituted or unsubstituted C3-C60 cycloalkylene group, a substituted or unsubstituted C2-C60 heterocycloalkylene group, a substituted or unsubstituted C2-C60 alkynylene group, A substituted or unsubstituted arylene group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;

R ₁₁ , R ₁₂ , R _13, R ₁₅ and R ₁₆ independently represent hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a 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, Unsuitable (Alkyl) amino group having 1 to 60 carbon atoms, di (alkyl having 1 to 60 carbon atoms), di (substituted or unsubstituted aryl) amino group having 6 to 60 carbon atoms, di (substituted or unsubstituted) 6 to 60 aryl) amino groups;

is a case of being an integer of 1 to 4, a is 2 or more at least two R ₁₃ are the same or different from each other, and, R ₁₃ is plural, each R ₁₃ may be been fused form.

* Is a bonding site with the pyrene group in the above-mentioned [A] or [B].

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, R ₁₁ , R ₁₂ and R ₁₃ in the above-mentioned structural formula 1 are independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted C2 to C20 alkyl group, a substituted or unsubstituted aryl group having 1 to 20 carbon atoms, A substituted or unsubstituted phenyl group, a substituted or unsubstituted pentalenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyl group, Azulenyl, substituted or unsubstituted heptalenyl, substituted or unsubstituted indacenyl, substituted or unsubstituted acenaphthyl, substituted or unsubstituted fluorenyl group ( fluorenyl), substituted or Substituted unsubstituted phenanthrenyl, substituted or unsubstituted anthryl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthryl, substituted or unsubstituted fluoranthenyl, Substituted naphthacenyl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrazinyl, Substituted or unsubstituted pyrrolenyl groups, substituted or unsubstituted pentacenyl groups, substituted or unsubstituted hexacenyl groups, substituted or unsubstituted pyrroles, Pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted imidazolinyl, substituted or unsubstituted imidazolyl, Imidazopyridinyl, substituted or unsubstituted < RTI ID = 0.0 > Substituted imidazopyrimidinyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, Indolyl, substituted or unsubstituted purinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted phthalazinyl, substituted or unsubstituted indolizinyl A substituted or unsubstituted indazolyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted cinnolinyl group, a substituted or unsubstituted indazolyl group indazolyl), substituted or unsubstituted carbazolyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenanthridinyl, substituted or unsubstituted pyranyl (pyranyl) ), Substituted or unsubstituted A substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzofuranyl group, Or an unsubstituted isothiazolyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, A substituted or unsubstituted dibenzopuranyl group, a substituted or unsubstituted triazinyl group, or a substituted or unsubstituted oxadiazolyl group.

More specifically, R ₁₁ , R ₁₂ and R ₁₃ in the above-mentioned structural formula 1 may independently be a pyrene-based derivative represented by one of the following formulas (4A) to (4H).

 In formulas (4A) to (4H)

Z ₁ to Z ₇ are, independently of each other, hydrogen; heavy hydrogen; A halogen atom; A hydroxyl group; Cyano; A nitro group; An amino group; An amidino group; Hydrazine; Hydrazone; A carboxyl group or a salt thereof; Sulfonic acid group or its salt; Phosphoric acid or its salts; An alkyl group having 1 to 10 carbon atoms; An alkoxy group having 1 to 10 carbon atoms; An alkylthio group having 1 to 10 carbon atoms; An alkyl group having 1 to 10 carbon atoms which is substituted with at least one of a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, An alkyl group having 1 to 10 carbon atoms and an alkylthio group having 1 to 10 carbon atoms; A phenyl group; Naphthyl group; A fluorenyl group; A phenanthrenyl group; Anthryl group; Pyrenyl; A crycenyl group; An alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a salt of a carboxyl group or a salt thereof, A phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, and a klycenyl group substituted with at least one of an alkoxy group having 1 to 10 carbon atoms and an alkylthio group having 1 to 10 carbon atoms; Indole diarrhea; A benzimidazolyl group; Carbazolyl group; Imidazolyl group; An imidazolinyl group; Imidazopyridinyl group; An imidazopyrimidinyl group; A pyridinyl group; A pyrimidinyl group; Triazinyl groups; A quinolinyl group; An alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a salt of a carboxyl group or a salt thereof, An imidazolyl group, an imidazopyridinyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, , An imidazopyrimidinyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and a quinolinyl group; Di (alkyl having 1 to 10 carbon atoms) amino group; And an aryl group having 1 to 10 carbon atoms, and the aryl group having 6 to 10 carbon atoms is selected from the group consisting of a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, and a klycenyl group . ≪ / RTI >

In the present invention, X ₂ in the structural formula 1 may be a single bond.

In the present invention, L ₁ in the structural formula 1 represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted pentalenylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted naphthylene group, a substituted Or a substituted or unsubstituted thiophenylene group, a substituted or unsubstituted azulenylene group, a substituted or unsubstituted heptolenylene group, a substituted or unsubstituted indacenylene group, a substituted or unsubstituted acenaphthylene group, a substituted or unsubstituted fluorenylene group, A substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted fluoranthenylene group, a substituted or unsubstituted triphenylenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted phenanthrenylene group, Substituted or unsubstituted naphthacenylene groups, substituted or unsubstituted pyrenylene groups, substituted or unsubstituted pyrenylene groups, substituted or unsubstituted pendanthenylene groups, A substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted imidazolylene group, , A substituted or unsubstituted imidazopyridinylene group, a substituted or unsubstituted imidazopyrimidinylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted pyrimidine group A substituted or unsubstituted indolylene group, a substituted or unsubstituted indolylene group, a substituted or unsubstituted indolylene group, a substituted or unsubstituted indolylene group, a substituted or unsubstituted indolylene group, a substituted or unsubstituted indolylene group, , A substituted or unsubstituted naphthyridinylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted sienolylene group, a substituted or unsubstituted indazolylene group, a substituted or unsubstituted carbazolylene group, A substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted phenanthrene group, Substituted or unsubstituted benzothiophenylene groups, substituted or unsubstituted benzothiophenylene groups, substituted or unsubstituted benzothiophenylene groups, substituted or unsubstituted benzothiophenylene groups, substituted or unsubstituted benzothiophenylene groups, substituted or unsubstituted benzothiophenylene groups, substituted or unsubstituted benzothiophenylene groups, A substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted triazylene group, or a substituted or unsubstituted oxadiazolene group. Lt; / RTI >

More specifically, L < ₁ > may be a single bond.

More specifically, the present invention relates to a compound represented by the above formula (A) wherein only one selected from the substituents Y ₄ and Y ₉ is a substituent represented by the above-mentioned [formula 1], and the substituent Y ₁ to Y ₃ and Y ₆ - Y < ₈ > may be a substituent represented by the above-mentioned [formula 1].

As yet another specific example, the above-mentioned [Chemical Formula A] the substituent Y ₄ and Y ₉ are each the [formula 1], and the substituent represented by, and [Chemical Formula B] in the Y ₁ to one and Y ₆ to selected from the group consisting of Y ₃ And Y < ₈ > may each be a substituent represented by the above-mentioned [formula 1].

More specifically, in the present invention, the structural formula 1 may be represented by any one of the following formulas (2A) to (2F).

         &Lt; Formula 2A > < EMI ID =

           &Lt; Formula 2C > < Formula 2D >

          &Lt; Formula (2E) >

Among the above formulas (2A) to (2F), L ₁ and R ₁₁ To R &lt; ₁₃ &gt;, a and * are the same as described above; R ₄₀ To R &lt; ₅₁ &gt; independently from each other are hydrogen; heavy hydrogen; A halogen atom; A hydroxyl group; Cyano; A nitro group; An amino group; An amidino group; Hydrazine; Hydrazone; A carboxyl group or a salt thereof; Sulfonic acid group or its salt; Phosphoric acid or its salts; An alkyl group having 1 to 10 carbon atoms; An alkoxy group having 1 to 10 carbon atoms; An alkylthio group having 1 to 10 carbon atoms; An alkyl group having 1 to 10 carbon atoms which is substituted with at least one of a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, An alkyl group having 1 to 10 carbon atoms and an alkylthio group having 1 to 10 carbon atoms; A phenyl group; Naphthyl group; A fluorenyl group; A phenanthrenyl group; Anthryl group; Pyrenyl; A crycenyl group; An alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a salt of a carboxyl group or a salt thereof, A phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, and a klycenyl group substituted with at least one of an alkoxy group having 1 to 10 carbon atoms and an alkylthio group having 1 to 10 carbon atoms; Indole diarrhea; A benzimidazolyl group; Carbazolyl group; Imidazolyl group; An imidazolinyl group; Imidazopyridinyl group; An imidazopyrimidinyl group; A pyridinyl group; A pyrimidinyl group; Triazinyl groups; A quinolinyl group; An alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a salt of a carboxyl group or a salt thereof, An imidazolyl group, an imidazopyridinyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, , An imidazopyrimidinyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and a quinolinyl group; Di (alkyl having 1 to 10 carbon atoms) amino group; And an aryl group having 6 to 20 carbon atoms, and the aryl group having 6 to 20 carbon atoms is selected from the group consisting of a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, Or the like.

More specifically, when the structural formula 1 in the pyrene-based derivative of the present invention is represented by any one of the above-mentioned formulas (2A) to (2F), in the structural formula (1), R ₁₁ to R ₁₃ independently represent hydrogen; heavy hydrogen; A halogen atom; A hydroxyl group; Cyano; A nitro group; An amino group; An amidino group; Hydrazine; Hydrazone; A carboxyl group or a salt thereof; Sulfonic acid group or its salt; Phosphoric acid or its salts; An alkyl group having 1 to 10 carbon atoms; An alkoxy group having 1 to 10 carbon atoms; An alkylthio group having 1 to 10 carbon atoms; Which is substituted with at least one member selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group, An alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms; Or the like.

In this case, 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), and in the formula (B), among the substituents Y ₁ to Y ₃ and Y ₆ to Y ₈ And the substituents Y ₄ and Y ₉ are each a substituent represented by the above-mentioned formula [1], and in formula [B], Y ₁ to Y ₃ and any one of Y ₆ to Y ₈ may be a substituent represented by the above-mentioned [formula 1].

In this case, X ₂ in the formula 1 may be a single bond.

Further, in the pyrene derivative compound according to the above [Formula A] or [Formula B], [Formula 1] may be any one selected from the group consisting of the following Substituent 1 to Substituent 65.

   [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]

More specifically, in the present invention, 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.

More specifically, the R &lt; ₅ &gt; 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.

The benzene ring and Cy in the following structural formula 1 of the present invention are fused to each other with the nitrogen atom and X ₂ interposed therebetween. For example, when X &lt; ₂ &gt; is a single bond, the indoline may be formed in the structural formula 1, and the indoline may contribute to enhancement of the luminous efficiency. Therefore, the pyrene derivative containing the structural formula 1 can provide excellent luminous efficiency.

[Structural formula 1]

In Formula 1, Cy is a saturated ring. The electron donor strength of Cy is smaller than the electron donor strength of an unsaturated ring (for example, benzene) in which electrons are delocalized. By using the condensed ring compound containing the structural formula 1 including Cy, the emission wavelength in the dark blue region can be obtained.

On the other hand, the nitrogen atom of the structural formula 1 may be bonded to the pyrene group through L ₁ .

In this case, the energy band gap of the condensed ring compound can be controlled by the above-mentioned L1 to control the emission wavelength.

In driving an organic light emitting device employing such a condensed cyclic compound between a pair of electrodes (an anode and a cathode), the condensed cyclic compound is generated in an organic layer between a pair of electrodes, between organic layers or between an organic layer and an electrode An organic light emitting device employing the condensed cyclic compound can have excellent driving voltage, efficiency, brightness, and lifetime characteristics.

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 or secondary amine derivative

(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.

Accordingly, the compound of the formula (A) of the present invention can be obtained by replacing at least one of the halogen at positions 4 and 9 of the pyrene with a secondary amine to obtain a pyrene derivative containing a tertiary amine having at least one substituent of the formula .

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 or secondary amine derivative

[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 pyrane derivative containing at least one tertiary amine having a substituent of the structural formula 1 is provided by substituting at least one of the positions 1 to 3 or 6 to 8 of the pyrene with the secondary amine of the above formula 1 .

The present invention also provides 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 pyrene derivative compound of the present invention.

In the present invention, the phrase "(organic layer) contains one or more pyrene derivative compounds" means that one kind of pyrene derivative compounds belonging to the category of the present invention (organic layer) Quot; may include two or more other condensed ring compounds. "

At this time, it is preferable that the layer containing the compound of the present invention is a light emitting layer sandwiched between the first electrode and the second electrode, and the organic layer includes a hole injecting layer, a hole transporting layer, a hole injecting function, At least one of a functional layer, a light emitting layer, an electron transporting layer, and an electron injecting layer which are simultaneously present.

In the present invention, the organic layer includes at least one of a hole injecting layer, a hole transporting layer, a functional layer having a hole injecting function and a hole transporting function (hereinafter referred to as "H-functional layer") (Hereinafter, referred to as "H-functional layer") having both the hole injection layer, the hole transporting layer, the hole injecting function and the hole transporting function Can be.

The condensed ring compound included in the light emitting layer may serve as a fluorescent dopant. For example, the condensed cyclic compound may serve as a blue fluorescent dopant that emits blue light. Alternatively, the condensed ring compound contained in the light emitting layer may serve as a fluorescent or phosphorescent host that emits red light, green light, or blue light.

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.

As a specific example of the present invention, a hole transport layer (HTL) may be additionally stacked, and an electron transport layer (ETL) may be further stacked between the cathode and the organic emission layer. The hole transport layer is laminated in order to facilitate the injection of holes from the anode. As the material of the hole transport layer, an electron donor molecule having a low ionization potential is used, and diamine, triamine or tetra Amine derivatives are widely used.

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

A 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).

&Lt; Formula 1 >

In Formula 1,

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), C ₁ -C ₁₀ alkoxynaphthyl group (for example, methylthiomethyl group, ethylthiomethyl 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

     BH25 BH26 BH27 BH28

      BH29 BH30 BH31 BH32

BH33 BH34 BH35 BH36

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

Synthesis Example 1-1. 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 5,10-dibromo-2,7-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 salts were removed by celite filtering, and the filtrate was dried. MeOH was added thereto and stirred vigorously to obtain 139 g (77.7%) of 4,4'-dibromo-2,2'-dinitro- .

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 the reaction solution was made basic by slowly adding 1 L of sodium hydroxide aqueous solution (1 L). Ethylacetate was added to extract the organic layer, and the organic layer was dried and concentrated. (87.7 g, 73.8%) of 4,4'-dibromo-2,2'-diaminobiphenyl was obtained by separating by column chromatography using hexane and methylene chloride as eluent.

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 (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, 0.7 g (0.0035 mol) of copper iodide and 1.6 g (0.0014 mol) of Pd (PPh3) 4 were introduced into a reactor under a nitrogen stream, It 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 (74.3%) of 4,4'-dibromo-2,2'-diphenylethynylbiphenyl obtained by column chromatography using hexane as eluent was obtained.

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

(1-B-5) Synthesis of pyrene B

[Reaction Scheme 13]

                                           Pyrene B

12.3 g (0.024 mol) of 4,4'-dibromo-2,2'-diphenylethynylbiphenyl was placed in a reactor under nitrogen flow 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 (16.3%) of 5,10-dibromo-2,7-diphenyl-pyrene.

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

Synthesis Example 1-2. Synthesis of cyclic amine derivatives having the structural formula 1

Synthesis Example 1-2-1: Synthesis of Intermediate 1-2-a

Intermediate 1-2-a was synthesized according to Scheme 14 below.

<Reaction Scheme 14>

                                                 1-2-a

50 g (0.462 mol) of phenylhydrazine and 170 ml of acetic acid were added to the reactor and heated to 60 占 폚. 51.9 g (0.462 mol) of 2-methylcyclohexanone was added dropwise to the heated flask, and the mixture was refluxed for 8 hours. After completion of the reaction, 100 ml of water was added and the mixture was basified with sodium hydroxide. The organic layer was extracted with water and ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography using hexane and ethyl acetate as eluent To give intermediate 1-2-a (72 g, 84% yield).

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

Intermediate 1-2-b was synthesized according to Scheme 15 below.

<Reaction Scheme 15>

                                            1-2-b

57 g (0.308 mol) of Intermediate 2-a and 570 ml of toluene were placed in a nitrogen atmosphere reactor and cooled to -10 ° C. 300 ml (0.474 mol) of 1.6M methyllithium was slowly added dropwise to the reaction solution, followed by reaction at -10 ° C for 3 hours, and water was slowly added until the reactivity was lost. The resulting reaction mixture was extracted with water and ethyl acetate, and the obtained organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and then separated by column chromatography using hexane and ethyl acetate as eluent to give intermediate 1-2-b (47 g, 76% yield).

Synthesis Example 1-3. Synthesis of pyrene derivative BD1 containing the cyclic amine substituent of the present invention

< Scheme 16 >

BD1

BD1

5.0 g (25 mmol) of the cyclic amine 2-b prepared in the above reaction scheme 15, 6.1 g (10 mmol) of the pyrene A, 0.1 g (0.4 mmol) of palladium acetate {Pd (OAc) ₂ } 3.8 g (41 mmol) of silicalbutoxide, 0.1 g (0.4 mmol) of tri-tert-butylphosphine and 80 ml of toluene were charged and reacted at a reaction temperature of 100 ° C for 2 hours. When the reaction was terminated, the temperature was lowered to room temperature. When crystals were formed, the crystals were separated by filtration and then column chromatography. And recrystallized with toluene and ethanol. The resulting solid was filtered and dried to obtain 1.5 g (yield: 19.7%) of pale yellow solid BD1.

MS (MALDI-TOF): m / z 753 [M] ^&lt; ^{+ &}

Synthesis Example 2. Synthesis of Compound BD 2

Synthesis was carried out in the same manner as in the synthesis of Intermediate 1-2-a except that 2-methylcyclohexanone was used instead of 2-methylcyclohexanone in Synthesis Example 1-2-1, intermediate 2-a ( 64.1 g, 81% yield).

<Reaction Scheme 17>

                                         2-a

<Reaction Scheme 18>

                                 2-b

Intermediate 2-b (52 g, yield 74%) was obtained in the same manner as in the synthesis of intermediate 1-2-b.

Also, compound BD 2 (11 g, yield: 18%) was synthesized by using the same method as in Synthesis Example 1-3 above using pyrene A.

Synthesis Example 3. Synthesis of compound BD 3

Compound BD3 (0.7 g, yield: 18%) was obtained by using 5.1 g (25 mmol) of the cyclic amine intermediate 1-2-b prepared in Synthesis Example 1-B of the present invention and the cyclic amine intermediate 1-2- %) Were synthesized.

Synthesis Example 4: Synthesis of compound BD 4

Intermediate 4-a (65 g, yield 80%) was obtained in the same manner as in Synthesis Example 1-2, except that 3-methylphenylhydrazine was used instead of phenylhydrazine in Synthesis Example 1-2 .

<Reaction Scheme 19>

                                      4-a

<Reaction Scheme 20>

                                           4-b

Also, Intermediate 4-b (51.4 g, yield 73%) was obtained in the same manner as in Synthesis Example 1-2-2.

Compound BD 4 (6 g, yield: 18%) was synthesized by using the same method as the synthesis method described in 1-3 above using pyrene A.

Synthesis Example 5. Synthesis of Compound BD 5

A white solid of compound BD5 (7.5 g, yield 19%) was obtained in the same manner as in Synthesis Example 4 except that the dihalopyrene intermediate was replaced with pyrene B in place of pyrene A in Synthesis Example 4.

Synthesis Example 6. Synthesis of Compound BD 6

Synthesis of 6-1-a

<Reaction Scheme 21>

                                                    6-1-a

50.0 g (232 mmol) of 4-b, 65.7 g (232 mmol) of 1-bromo-4-iodobenzene, 2.2 g (12 mmol) of copper iodide, 103.5 g (488 mmol) of 2-cyclohexanediamine and 53 g (464 mmol) of 2-cyclohexanediamine were added in this order, 500 ml of 1,4-dioxane was added thereto, and the mixture was refluxed and stirred for 1 day.

When the reaction was completed, the solution was filtered through a Celite filter and then separated by column chromatography. After recrystallization with hexane, the solid was filtered and dried to obtain Compound 6-1-a (36 g, yield 42%).

MS (MALDI-TOF): m / z 370 [M] ^&lt; ⁺ & gt ^;

Synthesis of 6-1-b

<Reaction Formula 22>

                                6-1-b

36.0 g (97 mmol) of the compound 6-1-a obtained from the above reaction scheme 21 was dissolved in 300 ml of tetrahydrofuran under a nitrogen stream, 73 ml (117 mmol) of 1.6 M n-butyllithium was slowly added dropwise while stirring at -78 ° C And when the dropwise addition is completed, stirring is carried out for 1 hour while maintaining the temperature at -78 ° C. Then, 14.2 g (136 mmol) of trimethyl borate was slowly added dropwise thereto, and the mixture was stirred at room temperature for 1 hour.

When the reaction is completed, 1 M hydrochloric acid aqueous solution is added dropwise at room temperature until it becomes acidic and stirred for 30 minutes. The mixture was extracted with ethyl acetate and water. The organic layer was concentrated under reduced pressure and recrystallized in hexane to obtain 19.5 g of a compound 6-1-b. (Yield 60%)

MS (MALDI-TOF): m / z 336 [M] ^&lt; ^{+ &}

6-2. Synthesis of pyrene derivative BD 6 containing the cyclic amine substituent of the present invention

<Reaction Scheme 23>

The 6-1-b 19.5g (58 mmol) prepared in Scheme 22 To a round bottom flask, the pyrene _{A 14.7g (24mmol), K 2} CO 3 (6.7g, 48mmol), Pd (PPh 3) 4 (0.6 g, 1 mmol) were added to a toluene 80 mL, 1,4-dioxane 80 mL, water 30 mL reactor and refluxed.

After completion of the reaction, the resulting crystals were filtered and recrystallized several times with toluene and acetone to synthesize Compound BD6 (5.2 g, yield: 23%).

MS (MALDI-TOF): m / z 934 [M] ^&lt; ^{+ &}

Synthetic example  7. Compound BD 7's  synthesis

< Scheme 24 >

                                                        7-a

7.5 g (37 mmol) of the cyclic amine 1-2-b prepared in the above reaction scheme 15, 20.0 g (39 mmol) of the pyrene B, 0.7 g (1 mmol) of {Pd ₂ (dba) ₃ } 0.5 g (1 mmol) of 2,2-bisdiphenylphosphino-1,1'-binaphthyl and 200 ml of toluene were fed into a flask, and the mixture was stirred at 80 ° C. for 6 hours Lt; / RTI &gt; When the reaction was terminated, the temperature was lowered to room temperature and crystals were formed, and the crystals were filtered and recrystallized from methanol. The resulting solid was filtered and dried to obtain 7-a (7.0 g, yield 28%).

MS (MALDI-TOF): m / z 632 [M] ^&lt; ^{+ &}

<Reaction Scheme 25>

7.0 g (11 mmol) of the 7-a prepared in the above reaction scheme 24 and 60 ml of tetrahydrofuran were added to the reactor under a nitrogen stream and 7.6 ml (12 mmol) of n-BuLi was slowly added while cooling to -78 ° C with stirring. At this time, heat is generated and quenched by adding 19 ml of water while cooling to -40 ° C again. The compound BD 7 (1.5 g, yield: 24.5%) was synthesized by recrystallization several times with toluene and acetone.

Synthesis Example 8. Synthesis of Compound BD8

Dibromo-1-nitrobenzene instead of 2,5-dibromo nitrobenzene 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%).

Compound BD8 (1.0 g, yield 21%) was synthesized by using 5.1 g (25 mmol) of 1,6-dibromo-5,10-diphenyl-pyrene and the above prepared cyclic amine intermediate 1-2-b .

Examples 2 to 8

The ITO glass was patterned so as 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

The voltage, current density, luminance, color coordinates, and lifetime of the organic electroluminescent device manufactured according to Examples 2, 3, 4, 6, 7, 8, and 9 and Comparative Examples 1 and 2 were measured, The results are shown in Table 1 below. 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 4.1 10 710 0.14 0.13 148 Example 3 3.9 10 760 0.14 0.13 170 Example 4 4.0 10 790 0.14 0.13 155 Example 6 4.1 10 790 0.14 0.14 145 Example 7 4.3 10 730 0.14 0.13 141 Example 8 3.9 10 770 0.14 0.13 158 Example 9
Pyrene B + substituent 40 4.0 10 720 0.14 0.12 138 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 a low driving voltage and is excellent in light emission characteristics such as brightness and lifetime 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 (18)

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

In the above formula (B)
R ₄ and R ₉ are the same or different from each other and each independently represents a hydrogen atom, a deuterium atom, 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 aryl group having 5 to 50 carbon atoms, a nitrile group, a nitro group, and a halogen group, and may form a condensed ring of an aliphatic or aromatic group with an adjacent group,
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, and may form a condensed ring of an aliphatic or aromatic group with an adjacent group,
Y ₁ , Y ₃ , Y ₆ and Y ₈ are the same or different and are each independently a substituent as defined for R ₄ and R ₉ ,
Provided that Y ₂ and Y ₇ are the same or different and are each independently a substituent represented by the following structural formula 1:
[Structural formula 1]

In the above structural formula 1,
Cy is a substituted or unsubstituted cycloalkylene group having 3 to 8 carbon atoms, and the hydrogen atoms substituted on the Cy may be substituted with deuterium or alkyl, and are the same as or different from each other;
X ₂ is a single bond;
L ₁ is a single bond or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms;
R ₁₁ , R ₁₂ , R _13, R ₁₅ and R ₁₆ are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, An aryl group having 6 to 60 carbon atoms which is unsubstituted;
a is an integer of 1 to 4, and when a is 2 or more, 2 or more R &lt; ₁₃ &gt; are the same or different from each other;
* Is a binding site with the pyrene group in the above formula (B);
The 'substituted' in the 'substituted or unsubstituted' means that the substituent is substituted with at least one substituent selected from the group consisting of deuterium, cyano, and halogen, provided that the compound represented by the following formula do.

(66) delete The method according to claim 1,
R ₁₁ , R ₁₂ and R ₁₃ in the above-mentioned structural formula 1 are independently selected from pyrene-based derivatives represented by one of the following formulas (4A) and (4E) to (4F)

In the above formulas 4A and 4E to 4F,
Z ₁ to Z ₇ are, independently of each other, hydrogen; heavy hydrogen; A halogen atom; Cyano; A nitro group; An alkyl group having 1 to 10 carbon atoms; A phenyl group; Naphthyl group; A fluorenyl group; A phenanthrenyl group; Anthryl group; Pyrenyl; And a cresyl group. delete The method according to claim 1,
Wherein L _&lt; 1 &gt; in the structural formula 1 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted pentalanylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted naphthylene group, A substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted triphenylenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted pyrenylene group, A substituted or unsubstituted naphthacene group, a substituted or unsubstituted naphthacene group, a substituted or unsubstituted naphthacene group, a substituted or unsubstituted naphthacene group, a substituted or unsubstituted naphthacene group, a substituted or unsubstituted pyrazylene group, And an unsubstituted naphthyridinylene group, wherein the pyrene-based derivative 6. The method of claim 5,
Wherein L _&lt; 1 &gt; in the structural formula (1) is a single bond. delete The method according to claim 1,
Wherein the structural formula 1 is represented by any one of the following formulas (2A) to (2F):
&Lt; Formula 2A >< EMI ID =

&Lt; Formula 2C &gt;&lt; Formula 2D &gt;

&Lt; Formula (2E) &gt;

Among the above-mentioned formulas (2A) to (2F), L ₁ , R ₁₁ to R ₁₃ , a and * have the same meanings as defined in claim 1;
R ₄₀ to R ₅₁ independently from each other are hydrogen; heavy hydrogen; A halogen atom; Cyano; A nitro group; An alkyl group having 1 to 10 carbon atoms; A phenyl group; Naphthyl group; A fluorenyl group; A phenanthrenyl group; Anthryl group; Pyrenyl; A phenanthracene derivative, a phenanthrene derivative, 9. The method of claim 8,
Wherein, in the formula 1, R ₁₁ to R ₁₃ independently represent hydrogen; heavy hydrogen; And an alkyl group having 1 to 10 carbon atoms. delete delete The method according to claim 1,
In the above formula (B), the [formula 1]
[Substituent group 1] to [Substituent group 20], [Substituent group 23] to [Substituent group 28], [Substituent group 31] to [Substituent group 36] , [Substituent group 58] to [Substituent group 60].
[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 23] [Substituent group 24]

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

[Substituent 28]

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

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

[Substituent group 38]

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

[Substituent 56]

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

13. The method of claim 12,
The R ₅ And R ₁₀ Are each the same or different and are each independently any one selected from a methyl group, an ethyl group, a propyl group, a butyl group, a cyclopentyl group, a cyclohexyl group, and a phenyl group. A first electrode;
A second electrode facing the first electrode; And
And an organic layer sandwiched between the first electrode and the second electrode, wherein the organic layer is formed of a material selected from the group consisting of the first, the third, the fifth, the sixth, the eighth, the ninth, the twelfth, 14. An organic light emitting device comprising at least one pyrene based derivative compound according to any one of claims 1 to 13. 15. The method of claim 14,
Wherein the organic layer interposed between the first electrode and the second electrode is a light emitting layer. 15. The method of claim 14,
Wherein the organic layer includes 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. 16. The method of claim 15,
Wherein the light emitting layer further comprises a host, and the pyrene derivative compound contained in the light emitting layer serves as a dopant, 18. The method of claim 17,
Wherein the host is an anthracene-based compound represented by the following Formula 1:
&Lt; Formula 1 >

In Formula 1,
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;
The 'substitution' in the 'substituted or unsubstituted' means that the substituent is substituted with at least one substituent selected from the group consisting of deuterium, cyano, and halogen.

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