KR20150052989A - Pyrene derivatives comprising heteroaryl amine group and organic light-emitting diode including the same - Google Patents

Abstract

The present invention relates to a pyrene derivative represented by chemical formula A, and an organic light-emitting diode including the same. In the chemical formula A, substituents Z, Ar_1, Ar_2, R_1 to R_5, connecting groups L_1 and L_2, and X, m, p and q are the same as defined in a detailed description of the present invention.

Description

[0001] The present invention relates to a pyrene derivative containing a heteroarylamine group and an organic light emitting device comprising the same,

The present invention relates to a pyrene derivative containing a heteroarylamine group and an organic light emitting diode including the same. More particularly, the present invention relates to a pyrene derivative which has excellent brightness and luminous efficiency when used as an organic light emitting material, And an organic light emitting device including the pyrene derivative.

Recently, as the size of a display device has been increased, a demand for a display device or a bendable display device having little space occupation due to a flat plate structure has been increasing. The liquid crystal display, which is a typical flat display device, is lighter than a conventional CRT However, it is disadvantageous in that a viewing angle is limited and a back light is necessarily required. In contrast, an organic light emitting diode (OLED), a new flat display device, is a display using an auto-luminescent phenomenon and has advantages such as a large viewing angle, a light weight and a small size compared to a liquid crystal display, In recent years, application to a full-color display or illumination is expected.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

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

When current is applied to the organic light emitting device, holes and electrons are injected from the anode and the cathode, respectively, and the injected holes and electrons recombine in the light emitting layer through the respective hole transporting layers and electron transporting layers to form luminescent excitons. The thus formed luminescent excitons emit light while transitioning to the ground state. The light may be divided into fluorescence using a singlet exciton and phosphorescent triplet exciton according to a light emitting mechanism, and the fluorescence and phosphorescence may be used as a light source of an organic light emitting device.

On the other hand, when only one material is used as the light emitting material, there arises a problem that the maximum light emitting wavelength shifts to a long wavelength due to intermolecular interaction, the color purity drops, 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 to increase the efficiency of light emission through the transition.

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.

Recently, there is an increasing need for high luminance and high color purity organic luminescent materials for applications in full-color displays or lighting. As the organic luminescent material, Patent Document 10-10-2010-0097181 (Sep. 02, 2010) discloses an organic light emitting device using an amine-bonded pyrene-based derivative containing a benzofuran or dibenzofurane group as a substituent, In publication No. US 5645948 (July 7, 1997), an organic light emitting device using a pyrene-based derivative in which benzoxazole group is directly bonded to pyrene is disclosed.

However, in spite of the above efforts, there is a continuing need to develop a novel organic light emitting material having superior luminance and luminescence efficiency and long life characteristics as compared with the organic light emitting materials manufactured by the prior art including the prior art It is a fact that is demanded.

Patent Document 1: Japanese Patent Application Laid-Open No. 10-2010-0097181 (2010.09.02)

US Patent Publication No. US 5645948 (July 7, 1997)

Therefore, the first technical object of the present invention is to provide a novel organic compound which can be used in the light emitting layer of an organic light emitting diode (OLED), exhibits excellent luminance and luminous efficiency, Emitting material.

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

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

(A)

In the above formula (A)

X is one selected from O, S and Se,

The linking groups L ₁ and L ₂ are the same or different and independently of one another are a single bond, a substituted or unsubstituted arylene group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroatom selected from O, N, S and Si Or a heteroarylene group having 2 to 50 carbon atoms,

Ar ₁ and Ar ₂ are the same or different and independently of each other, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, or a substituted or unsubstituted heteroatom selected from O, N, S and Si Lt; / RTI > is a heteroaryl group having 2 to 50 carbon atoms,

Each substituent M which is bonded to the nitrogen atom of the amine group may be the same or different,

Wherein _one of R ₁ to R ₄ in the substituent M is a single bond bonded to a nitrogen atom,

R ₁ to R ₅ are the same or different from each other and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, Substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkyl, An alkenyl group, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having at least one heteroatom selected from O, N, S and Si, 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 alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, A substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, An amino group, an amino group, an amino group, an amino group, an amino group, an amino group, a nitro group, a halogen group,

Each carbon atom in the pyrene ring is bonded to the nitrogen atom of the amine or, when not bonded to the substituent Z, to hydrogen;

m is an integer of 1 to 8, and when m is 2 or more, each Z is the same or different from each other,

p and q are the same or different integers of 1 to 3, and when p is 2 or more, each Ar ₁ is the same or different, and when q is 2 or more, each Ar ₂ is the same or different from each other.

According to another aspect of the present invention, there is provided 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, An organic light emitting device comprising at least one organic light emitting compound represented by Formula (A) of the present invention is provided.

According to the present invention, the compound represented by the above-mentioned formula (A) has excellent luminance and luminous efficiency and exhibits excellent device characteristics with a longer lifetime as compared with a conventional material, and can be used for a device for manufacturing a full color display .

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

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

The present invention provides an organic luminescent compound which can be used for a luminescent layer of an organic luminescent device, which comprises a pyrene derivative represented by the following formula (A).

 (A)

In the above formula (A)

X is one selected from O, S and Se,

The linking groups L ₁ and L ₂ are the same or different and independently of one another are a single bond, a substituted or unsubstituted arylene group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroatom selected from O, N, S and Si Or a heteroarylene group having 2 to 50 carbon atoms,

Ar ₁ and Ar ₂ are the same or different and independently of each other, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, or a substituted or unsubstituted heteroatom selected from O, N, S and Si Lt; / RTI > is a heteroaryl group having 2 to 50 carbon atoms,

Each substituent M which is bonded to the nitrogen atom of the amine group may be the same or different,

Wherein _one of R ₁ to R ₄ in the substituent M is a single bond bonded to a nitrogen atom,

R ₁ to R ₅ are the same or different from each other and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, Substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkyl, An alkenyl group, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having at least one heteroatom selected from O, N, S and Si, 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 alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, A substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, An amino group, an amino group, an amino group, an amino group, an amino group, an amino group, a nitro group, a halogen group,

Each carbon atom in the pyrene ring is bonded to the nitrogen atom of the amine or, when not bonded to the substituent Z, to hydrogen;

m is an integer of 1 to 8, and when m is 2 or more, each Z is the same or different from each other,

p and q are the same or different integers of 1 to 3, and when p is 2 or more, each Ar ₁ is the same or different, and when q is 2 or more, each Ar ₂ is the same or different,

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

In consideration of the range of the alkyl or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms" and "substituted or unsubstituted aryl group having 5 to 50 carbon atoms" in the present invention, The carbon number of the alkyl group having 1 to 30 carbon atoms and the aryl group having 5 to 50 carbon atoms means the total number of carbon atoms constituting the alkyl moiety or the aryl moiety when it is considered that the substituent is not substituted without considering the substituted moiety will be. For example, a phenyl group substituted with a butyl group at the para position should be considered to correspond to an aryl group having 6 carbon atoms substituted with a butyl group having a carbon number of 4.

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

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

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

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

Specific examples of the alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, hexyloxy, At least one hydrogen atom in the alkoxy group may be substituted with the same substituent as in the case of the aryl group.

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

The pyrene derivative of the present invention is characterized by being a compound represented by the above formula (A).

More specifically, the formula (A) is characterized in that the nitrogen of the amine group bonded to the pyrene contains the substituent M.

The substituent M may have a structure of a substituted or unsubstituted benzoxazole group, a substituted or unsubstituted benzothiazole group or a substituted or unsubstituted benzene selenazole group according to the atom X in the 5-membered ring. Since the substituent M is bonded to the nitrogen atom, the pyrene derivative in the present invention is a dopant material having superior luminance and luminous efficiency as compared with the existing material, and can have a long-lasting effect.

At this time, the luminescent properties of the organic luminescent material can be controlled by changing the kinds of the substituents R 1 to R 5 of the benzoxazole group, the benzthiazole group or the benz selenazole group of the substituent M, or by changing the kinds of other substituents bonded to the amine have.

In the present invention, Ar ₁ and Ar ₂ may be an aryl group or a heteroaryl group, respectively.

When Ar ₁ and Ar ₂ are the same or different and each is a heteroaryl group, the heteroaryl group may be any one selected from Substituents 101 to 117, but is not limited thereto.

[Substituent 101] [Substituent 102] [Substituent 103] [Substituent 104]

[Substituent group 105] [Substituent group 106] [Substituent group 107]

[Substituent group 108] [Substituent group 109] [Substituent group 110]

[Substituent group 111] [Substituent group 112] [Substituent group 113]

[Substituent group 114] [Substituent group 115] [Substituent group 116]

[Substituent group 117]

Wherein R is the same or different and is independently selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted alkylthio 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 6 to 50 carbon atoms, a substituted or unsubstituted arylthio group having 1 to 30 carbon atoms, Or a substituted or unsubstituted aryloxy group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, (Substituted or unsubstituted alkyl group having 1 to 30 carbon atoms), a di (substituted or unsubstituted C1 to C30 alkyl) amino group, a substituted or unsubstituted C6 to C30 arylamino group, a substituted or unsubstituted An aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, germanium, phosphorus, and boron, Substituents may be bonded to adjacent groups to form a saturated or unsaturated ring,

n is an integer of 1 to 9,

When the substituent R is not bonded to the carbon in the aromatic ring or the saturated hydrocarbon ring in the above [substituent groups 101] to [substituent group 117], hydrogen is bonded,

When the substituent R is 2 or more, each R may be the same or different from each other,

One of the substituents R in the above [substituent groups 101] to [substituent group 117] is a single bond which binds to the linking group L ₁ or L ₂ in the above formula (A)

The 'substitution' in the 'substituted or unsubstituted' is the same as defined above.

In addition, when Ar ₁ and Ar ₂ are the same or different aryl groups, the aryl group may be any one selected from the following [substituent groups 201] to [substituent group 210], but is not limited thereto.

[Substituent group 201] [Substituent group 202] [Substituent group 203]

[Substituent group 204] [Substituent group 205] [Substituent group 206]

[Substituent group 207] [Substituent group 208] [Substituent group 209]

[Substituent 210]

Wherein n is an integer of 1 to 9,

When the substituent R is not bonded to the carbon in the aromatic rings in the [substituent groups 201] to [substituent group 210], hydrogen is bonded, and the substituent group R is as defined above.

In the present invention, the linking groups L ₁ and L ₂ may each be a single bond, or may be any one selected from the following formulas (101) to (210).

[Structural Formula 101] [Structural Formula 102] [Structural Formula 103] [Structural Formula 104]

[Structural Formula 105] [Structural Formula 106] [Structural Formula 107]

[Structural Formula 108] [Structural Formula 109] [Structural Formula 110]

[Structural Formula 111] [Structural Formula 112] [Structural Formula 113]

[Structural Formula 114] [Structural Formula 115] [Structural Formula 116]

[Structural Formula 117]

[Structural Formula 201] [Structural Formula 202] [Structural Formula 203]

[Structural Formula 204] [Structural Formula 205] [Structural Formula 206]

[Structural Formula 207] [Structural Formula 208] [Structural Formula 209]

[Structural Formula 210]

Wherein n is an integer from 2 to 9,

In the case where the substituent R is not bonded to the aromatic ring or the carbon in the saturated hydrocarbon ring in the above structural formulas 101 to 210,

Two to four R's of the substituents R included in the above Structural Formulas 101 to 210 are respectively a single bond bonded to the nitrogen atom and the substituent Ar ₁ or a single bond bonded to the nitrogen atom and the substituent Ar ₂ ,

Wherein the substituent R is the same as defined above.

The substituent Z substituted on the pyrene skeleton is more specifically a group selected from the group consisting of deuterium, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3- Or a cycloalkyl group having 1 to 30 carbon atoms.

In the present invention, the pyrene derivative of the formula (A) may be bonded to the amine at positions 1, 6 or 2,7 respectively in the pyrene structure described in the following structural formula (a).

[Structural Formula a]

In the present invention, the above-mentioned pyrene derivatives may have the same or different two amine groups, and when the two amine groups are the same, they may be obtained by reacting the same kind of amine with a halogenated pyrene such as dibromopyrene And when two amine groups are different, they can be obtained by sequentially reacting each different kind of amine.

When a different amine is sequentially reacted as described above, the pyrene derivative having an amine group bonded thereto as an intermediate may be purified and then reacted with a new amine in the next step. When the two amines are different as described above, the resulting pyrene derivative is obtained as an asymmetric compound.

Examples of the substituent which is substituted for each possible functional group in M, L ₁ , L ₂ , Ar ₁ and Ar ₂ include a cyano group, a halogen group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 18 carbon atoms , An arylalkyl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkylsilyl group having 1 to 12 carbon atoms, and an arylsilyl group having 6 to 18 carbon atoms.

In the present invention, M or Ar ₁ or Ar ₂ bonded to the amine of the above formula (A) may include deuterium. Substituents substitutable for M or Ar ₁ or Ar ₂ bonded to the amine may also include deuterium.

Preferably, the hydrogen atoms bonded to the aromatic ring of M or Ar < ₁ > or Ar &_lt; ₂ > may be substituted with deuterium.

In general, the deuterium-substituted compound exhibits a lower zero energy and lower vibration energy level because the atomic mass of deuterium is two times larger than that of hydrogen, as compared to a compound bonded with hydrogen. In addition, physicochemical properties such as chemical bond lengths related to deuterium appear to be different from hydrogen, and in particular, the CD bond elongation amplitude is smaller than that of CH bonds, so that the van der Waals radius of deuterium is smaller than hydrogen, Indicating that the bond is shorter and stronger than the CH bond.

In addition, when substituted with deuterium, the energy of the bottom state is lowered. As the bond length of deuterium and carbon becomes shorter, the molecular hardcore volume is reduced, and thus, the electro polar polarizability can be reduced, It is known that the thin film volume can be increased by weakening the intermolecular interaction. Such characteristics can make the effect of lowering the crystallinity of the thin film, that is, amorphous state, and can generally be effective for increasing the lifetime and driving characteristics of the organic light emitting device, and the heat resistance can be further improved.

The pyrene derivative of the formula (A) of the present invention may be any one selected from the following [compound 1] to [compound 117].

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[Compound 85] [Compound 86] [Compound 87]

[Compound 88] [Compound 89] [Compound 90]

[Compound 91] [Compound 92] [Compound 93]

[Compound 94] [Compound 95] [Compound 96]

[Compound 97] [Compound 98] [Compound 99]

[Compound 100] [Compound 101] [Compound 102]

[Compound 103] [Compound 104] [Compound 105]

[Compound 106] [Compound 107] [Compound 108]

[Compound 109] [Compound 110] [Compound 111]

[Compound 112] [Compound 113] [Compound 114]

[Compound 115] [Compound 116] [Compound 117]

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 includes at least one organic electroluminescent compound according to the present invention.

In the present invention, the phrase "(organic layer) contains at least one organic compound" means that one organic compound belonging to the category of the present invention (organic layer) or two or more different compounds belonging to the category of organic compound May be included.

The organic layer containing the organic luminescent compound of the present invention may include 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, have. At this time, the organic layer interposed between the first electrode and the second electrode may include a light emitting layer, and the organic light emitting compound of the present invention may be used as a dopant.

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

In the present invention, as the electron transporting layer material, a known electron transporting material can be used as a material that stably transports electrons injected from an electron injection electrode (cathode). Examples of known electron transporting materials include quinoline derivatives, especially tris (8-quinolinolate) aluminum (Alq3), TAZ, Balq, beryllium bis (benzoquinolin-10- but are not limited to, materials such as olate: Bebq2), ADN, compound 201, compound 202, BCP, oxadiazole derivative PBD, BMD, BND and the like.

TAZ BAlq

&Lt; Compound 201 > < Compound 202 > BCP

In addition, the electron transporting layer used in the present invention can be used alone or in combination with the electron transporting layer material as the organometallic compound represented by the formula (C).

 &Lt; RTI ID = 0.0 &

In the above formula (C)

Y is a moiety selected from C, N, O and S, which is directly bonded to M to form a single bond, and any moiety selected from C, N, O and S is a moiety coordinating to M And is a ligand chelated by coordination bond with the single bond,

Wherein M is an alkali metal, an alkaline earth metal, an aluminum (Al), or a boron (B) atom, and OA is a monovalent ligand capable of single bond or coordination bond with M,

O is oxygen,

A represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted C2 to C20 A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, and a substituted or unsubstituted hetero atom selected from O, N, S and Si And a heteroaryl group having 2 to 50 carbon atoms,

M is 1 and n is 0 when M is a metal selected from an alkali metal,

M = 1, n = 1, or m = 2 and n = 0 when M is a metal selected from alkaline earth metals,

M is from 1 to 3 when M is boron or aluminum, and n is any of from 0 to 2, and m + n = 3;

The 'substituted' in the 'substituted or unsubstituted' may be a substituent selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl, alkoxy, alkylamino, arylamino, heteroarylamino, alkylsilyl, An aryl group, an aryl group, a heteroaryl group, germanium, phosphorus, and boron.

In the present invention, Y may be the same or different and independently of each other may be any one selected from the following formulas [C1] to [C39], but is not limited thereto.

[Structural formula C1] [Structural formula C2] [Structural formula C3]

[Structural formula C4] [Structural formula C5] [Structural formula C6]

[Structural formula C7] [Structural formula C8] [Structural formula C9] [Structural formula C10]

[Structural formula C11] [Structural formula C12] [Structural formula C13]

[Structural formula C14] [Structural formula C15] [Structural formula C16]

[Structural formula C17] [Structural formula C18] [Structural formula C19] [Structural formula C20]

[Structural formula C21] [Structural formula C22] [Structural formula C23]

[Structural formula C24] [Structural formula C25] [Structural formula C26]

[Structural formula C27] [Structural formula C28] [Structural formula C29] [Structural formula C30]

[Structural formula C31] [Structural formula C32] [Structural formula C33]

[Structural formula C34] [Structural formula C35] [Structural formula C36]

[Structural formula C37] [Structural formula C38] [Structural formula C39]

In the above Structural Formula C1 to Structural Formula C39,

R is the same or different and is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C6-30 aryl, A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms And may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring.

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

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

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

A hole injection layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30.

The hole injection layer material is not particularly limited as long as it is conventionally used in the art. For example, 2-TNATA [4,4 ', 4 "-tris (2-naphthylphenyl-phenylamino) -triphenylamine] , NPD [N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'- biphenyl-4,4'-diamine], DNTPD [N, N'-diphenyl-N, N'-bis- [4- ], Etc. However, the present invention is not limited thereto.

The material for the hole transport layer is not particularly limited as long as it is commonly used in the art and includes, for example, N, N'-bis (3-methylphenyl) -N, N'- -Biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine (a-NPD). However, the present invention is not necessarily limited thereto.

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 . At this time, The blocking material is not particularly limited, but it should have an ionization potential higher than that of the light emitting compound while having an electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

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

The light emitting layer may be made of a host and a dopant.

Further, according to a specific example of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 ANGSTROM.

Here, the host used in the light emitting layer may be a compound represented by the following Chemical Formulas 1A to 1D.

&Lt; EMI ID =

In the above formula (1A)

Ar _7, Ar ₈ and Ar ₉ are the same or different and each independently represents a single bond, a substituted or unsubstituted C ₅ -C ₆₀ aromatic linking group, or a substituted or unsubstituted C ₂ -C ₆₀ heteroaromatic linking group;

R ₂₁ to R ₃₀ are the same or different from each other and each independently represents a hydrogen atom, a heavy hydrogen atom, 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 aryl group, A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, A substituted or unsubstituted 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 (alkyl) amino group having 1 to 60 carbon atoms, a di (substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, a substituted or unsubstituted amino group having 6 to 60 carbon atoms, Or an unsubstituted aryl group having 6 to 60 carbon atoms) amino 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, phosphorus, boron Each substituent may form a fused ring with the adjacent groups;

E, f and g are the same as or different from each other and each independently 0 or an integer of 1 to 4;

The two sites indicated by * in the anthracene may be the same as or different from each other, and may independently form an anthracene derivative selected from the following formulas (1Aa-1) to (1Aa-3) in combination with the P or Q structure.

[Chemical Formula 1Aa-1] [Chemical Formula 1Aa-2] Chemical Formula 1Aa-3]

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

&Lt; RTI ID = 0.0 &

In the above formula (1B)

Wherein Ar ₁₇ to Ar ₂₀ are the same or different from each other and each independently represent a substituent group as defined in Ar ₇ to Ar ₈ in Formula 1A, and R ₆₀ to R ₆₃ are the same as defined in R ₂₁ to R ₃₀ in Formula 1A Lt; / RTI &gt;

W and ww are the same as or different from each other, x and xx are the same as or different from each other, w + ww and x + xx are the same or different from each other and independently an integer of 0 to 3; Y and yy are the same or different, and z and zz are the same or different from each other, y + yy to z + zz are not more than 2, and each is an integer of 0 to 2;

[Chemical Formula 1C]

In the above formula (1C)

Wherein Ar ₂₁ to Ar ₂₄ are the same or different and are made of the same substituents as defined for Ar ₇ to Ar ₈ in the (1A) each independently from each other, wherein R ₆₄ to R ₆₇ is at R ₂₁ to R ₃₀ of Formula 1A Lt; / RTI &gt; is as defined above.

The above ee to hh are the same as or different from each other, and each independently is an integer of 1 to 4, and the above-mentioned II to 11 are the same or different and independently an integer of 0 to 4.

[Chemical Formula 1D]

In the above formula (1D)

Wherein Ar ₂₅ to Ar ₂₇ are the same or different from each other and each independently represent a substituent group as defined in Ar ₇ to Ar ₈ in formula (1A), and R ₆₈ to R ₇₃ are the same or different from each other, The substituent groups are the same as defined in R ₂₁ to R ₃₀ of 1 A, and each substituent may form a saturated or unsaturated cyclic structure adjacent to each other. In addition, the mm to ss are the same or different from each other and each independently an integer of 0 to 4.

More specifically, the host may be represented by any one selected from the group consisting of the following [host 1] to [host 56], but is not limited thereto.

[Host 1]    [Host 2] [Host 3]    [Host 4]

[Host 5]   [Host 6]       [Host 7]    [Host 8]

[Host 9]   [Host 10] [Host 11]    [Host 12]

[호스트13] [호스트14] [호스트15] [호스트16]

[Host 13] [Host 14] [Host 15] [Host 16]

[Host 17]   [Host 18] [Host 19]    [Host 20]

[Host 21]   [Host 22] [Host 23]    [Host 24]

[Host 25]   [Host 26] [Host 27]    [Host 28]

[Host 29]   [Host 30] [Host 31]    [Host 32]

[Host 33]    [Host 34] [Host 35]   [Host 36]

[Host 37]  [Host 38]     [Host 39]  [Host 40]

[Host 41]    [Host 42] [Host 43]     [Host 44]

[Host 45]    [Host 46] [Host 47]    [Host 48]

[Host 49]    [Host 50] [Host 51]     [Host 52]

[Host 53]    [Host 54] [Host 55]   [Host 56]

The light emitting layer may further include various dopants and various hosts as well as the dopant and the host.

In the present invention, at least one layer selected from the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer may be formed by a single molecular deposition method or a solution process. Here, the deposition method refers to a method of forming a thin film by evaporating a material used as a material for forming each of the layers through heating or the like under vacuum or low pressure, Refers to a method of mixing a material used as a material with a solvent and forming the thin film by a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating or the like.

Further, the organic light emitting device of the present invention may be a flat panel display device; A flexible display device; Monochrome or white flat panel illumination devices; And a single-color or white-colored flexible lighting device.

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.

(Example)

Synthetic example  1: Synthesis of formula (1)

Synthesis of Synthesis Example 1- (1): [Intermediate 1-a]

[Intermediate 1-a] was synthesized according to Reaction Scheme 1 below.

<Reaction Scheme 1>

                        [Intermediate 1-a]

Benzoic alcohol (31.0 g, 0.286 mol), 2-bromo-6-nitrophenol (25.0 g, 0.115 mol), iron chloride (III) (0.93 g, 5.7 mmol) Bis (diphenylphosphino) ferrocene (1.27 g, 2 mmol) and 25 ml of toluene were placed and the mixture was refluxed and stirred at 150 占 폚 for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, concentrated under reduced pressure, and then subjected to column separation. And recrystallized from petronium ether to obtain [intermediate 1-a]. (15.0 g, 48%).

Synthesis of Synthesis Example 1- (2): [Intermediate 1-b]

[Intermediate 1-b] was synthesized according to Reaction Scheme 2 below.

<Reaction Scheme 2>

                               [Intermediate 1-b]

1-Bromo-2,5-dimethylbenzene (25.0 g, 0.135 mol) and 200 ml of tetrahydrofuran were placed in a 1 L round bottom flask and cooled to -78 캜 under a nitrogen atmosphere. 1.6 M normal butyl lithium (101 ml, 0.162 mol) was added dropwise to the cooled solution. After stirring at the same temperature for 2 hours, trimethyl borate (18.2 g, 0.176 mol) was added dropwise. After stirring at room temperature for 1 hour, 1N hydrochloric acid was added to acidify the solution. Concentrated under reduced pressure, and recrystallized from n-hexane to obtain [intermediate 1-b]. (12.5 g, 62%).

Synthesis of Synthesis Example 1- (3): [Intermediate 1-c]

[Intermediate 1-c] was synthesized according to Reaction Scheme 3 below.

<Reaction Scheme 3>

                 [Intermediate 1-b] [Intermediate 1-c]

(10.0 g, 0.053 mol), [intermediate 1-b] (9.6 g, 0.064 mol), tetrakis (triphenylphosphine) palladium 1.2 g, 0.001 mol), potassium carbonate (14.8 g, 0.107 mol), toluene (50 ml), tetrahydrofuran (50 ml) and water (20 ml) After completion of the reaction, the reaction mixture was cooled to room temperature and the organic layer was separated and concentrated under reduced pressure. After separation by column chromatography, recrystallization from n-hexane gave [intermediate 1-c]. (10.0 g, 88%).

Synthesis of Synthesis Example 1- (4): [Intermediate 1-d]

[Intermediate 1-d] was synthesized according to Reaction Scheme 4 below.

<Reaction Scheme 4>

[Intermediate 1-c] [Intermediate 1-a] [Intermediate 1-d]

To a 100 ml round-bottomed flask was added [Intermediate 1-c] (8.5 g, 40 mmol), [intermediate 1-a] (10.0 g, 36 mmol), tris (dibenzylideneacetone) palladium (0.67 g, 0.7 mmol) (0.45 g, 0.7 mmol) of 2,2'-bis (diphenylphosphino) -1,1'-binaphthalene and 50 ml of toluene were placed and the mixture was stirred under reflux for 3 hours. The resultant was separated by column chromatography and recrystallized from methanol to obtain [intermediate 1-d]. (11 g, 75%)

Synthesis Example 1- (5): Synthesis of [Formula 1]

[Formula 1] was synthesized according to Reaction Scheme 5 below.

<Reaction Scheme 5>

[중간체 1-d] [화학식 1]

[Intermediate 1-d] [Chemical Formula 1]

Dibromopyrene (3.0 g, 8 mmol), [intermediate 1-d] (7.4 g, 18 mmol), tris (dibenzylideneacetone) palladium (0.31 g, 0.3 mmol) in a 250 ml round bottom flask, (4.2 g, 25 mmol), 2,2'-bis (diphenylphosphino) -1,1'-binaphthalene (0.21 g, 0.3 mmol) and toluene (80 ml) were added and the mixture was refluxed with stirring for 15 hours . The reaction mixture was separated by column chromatography, and recrystallized from ethyl acetate and heptane to obtain [Formula 1]. (3.0 g, 35%).

MS (MALDI-TOF): m / z 1008.42 [M ^&lt; ⁺ &^gt;

Synthesis Example 2: Synthesis of Formula 21

Synthesis of Synthesis Example 2- (1): [Intermediate 2-a]

[Intermediate 2-a] was synthesized according to Reaction Scheme 6 below.

<Reaction Scheme 6>

                        [Intermediate 2-a]

Bromo-2-methylbenzene (25.0 g, 0.146 mol) was used instead of 1-bromo-2,5-dimethylbenzene in the above Synthesis Example 1- (2) -a]. (12.5 g, 63%).

Synthesis of Synthesis Example 2- (2): [Intermediate 2-b]

[Intermediate 2-b] was synthesized according to the following Reaction Scheme 7.

<Reaction Scheme 7>

                               [Intermediate 2-b]

3-aminopyridine (25.0 g, 0.226 mol), dimethylsulfoxide (250 ml) and water (5 ml) were added to a 500 ml round bottom flask and N-bromosuccinimide (99.3 g, 0.558 mol) . The reaction solution was stirred at room temperature for 24 hours and then recrystallized from acetonitrile to obtain [intermediate 2-b]. (59 g, 89%)

Synthesis of Synthesis Example 2- (3): [Intermediate 2-c]

[Intermediate 2-c] was synthesized according to the following Reaction Scheme 8.

<Reaction Scheme 8>

[Intermediate 2-b] [Intermediate 2-a] [Intermediate 2-c]

Except that [Intermediate 2-b] was used instead of 1-amino-2-bromo-4-methylpyridine in the above Synthesis Example 1- (3) To give [intermediate 2-c]. (12 g, 73%)

Synthesis Example 2- (4): Synthesis of [intermediate 2-d]

[Intermediate 2-d] was synthesized according to the following Reaction Scheme 9.

<Reaction Scheme 9>

[중간체 2-c] [중간체 1-a] [중간체 2-d]

[Intermediate 2-c] [Intermediate 1-a] [Intermediate 2-d]

The procedure of Intermediate 2-c was repeated except that Intermediate 2-c was used instead of Intermediate 1-c in Synthesis Example 1- (4) to obtain Intermediate 2-d. (11 g, 64%).

Synthesis Example 2- (5): Synthesis of [Formula 21]

[Chemical Formula 21] was synthesized according to Reaction Scheme 10 below.

<Reaction formula 10>

[중간체 2-d] [화학식 21] 상기 합성예 1-(5)에서 [중간체 1-d] 대신 [중간체 2-d]를 사용한 것을 제외하고 동일한 방법으로 실험하여 [화학식 21]을 얻었다. (2.8g, 30%)

[Intermediate 2-d] The same procedure was followed except that [Intermediate 2-d] was used instead of [Intermediate 1-d] in the above Synthesis Example 1- (5) to obtain [Formula 21]. (2.8 g, 30%)

MS (MALDI-TOF): m / z 1132.45 [M ^&lt; ⁺ &^gt;].

Synthesis Example 3: Synthesis of Formula 39

Synthesis of Synthesis Example 3- (1): [Intermediate 3-a]

[Intermediate 3-a] was synthesized according to the following Reaction Scheme 11.

<Reaction Scheme 11>

               [Intermediate 3-a]

The same procedure was followed except that 2-nitro-4-bromophenol was used instead of 2-bromo-6-nitrophenol in Synthesis Example 1- (1) to obtain [Intermediate 3-a]. (16.0 g, 50%).

Synthesis of Synthesis Example 3- (2): [Intermediate 3-b]

[Intermediate 3-b] was synthesized according to Reaction Scheme 12 below.

<Reaction Scheme 12>

                 [Intermediate 3-b]

Intermediate 3-b] was obtained in the same manner as in Synthesis Example 1- (2) except that bromobenzene (25.0 g, 0.159 mol) was used instead of 1-bromo-2,5-dimethylbenzene. (13 g, 67%).

Synthesis of Synthesis Example 3- (3): [Intermediate 3-c]

[Intermediate 3-c] was synthesized according to the following Reaction Scheme 13.

<Reaction Scheme 13>

[3,5-dibromo-2-pyridylamine] [Intermediate 3-b] [Intermediate 3-c]

3,5-dibromo-2-pyridylamine was used in place of 1-amino-2-bromo-4-methylpyridine in Synthesis Example 1- (3) ] Was used to obtain [Intermediate 3-c]. (8 g, 68%).

Synthesis of Synthesis Example 3- (4): [Intermediate 3-d]

[Intermediate 3-d] was synthesized according to the following Reaction Scheme 14.

<Reaction Scheme 14>

[Intermediate 3-c] [Intermediate 3-a] [Intermediate 3-d]

[Intermediate 3-c] was used in place of [Intermediate 1-a] in the above Synthesis Example 1- (4), and [Intermediate 3-a] was used in place of [Intermediate 1-a] d]. (11 g, 72%).

Synthesis Example 3- (5): Synthesis of [Formula 39]

[Chemical Formula 39] was synthesized according to Reaction Scheme 15 below.

<Reaction Scheme 15>

[중간체 3-d] [화학식 39]

[Intermediate 3-d] [Formula 39]

The procedure of Synthesis Example 1- (5) was repeated except that [Intermediate 3-d] was used instead of [Intermediate 1-d] to obtain [Formula 39]. (2.6 g, 28%)

MS (MALDI-TOF): m / z 1104.42 [M ^&lt; ⁺ &^gt;

Synthesis Example 4: Synthesis of Compound (58)

Synthesis of Synthesis Example 4- (1): [Intermediate 4-a]

[Intermediate 4-a] was synthesized according to Scheme 16 below.

<Reaction Scheme 16>

                        [Intermediate 4-a]

In the same manner as in Synthesis Example 1- (1) except that 4-tert-butylbenzyl alcohol was used instead of benzyl alcohol and 2-nitro-4-bromophenol was used instead of 2- To obtain [intermediate 4-a]. (13.0 g, 41%).

Synthesis of Synthesis Example 4- (2): [Intermediate 4-b]

[Intermediate 4-b] was synthesized according to the following Reaction Scheme 17.

<Reaction Scheme 17>

                        [Intermediate 4-b]

The same procedure was followed except that 3,5-dimethylbenzene (25.0 g, 0.159 mol) was used instead of 1-bromo-2,5-dimethylbenzene in Synthesis Example 1- (2) . (13 g, 64%)

Synthesis of Synthesis Example 4- (3): [Intermediate 4-c]

[Intermediate 4-c] was synthesized according to the following Reaction Scheme 18.

<Reaction Scheme 18>

              [Intermediate 4-b] [Intermediate 4-c]

Was obtained in the same manner as in Synthesis Example 1- (3) except that 1-amino-3-bromo-5-fluorobenzene was used instead of [intermediate 4-b ] Was used to obtain [Intermediate 4-c]. (15 g, 88%).

Synthesis of Synthesis Example 4- (4): [Intermediate 4-d]

Intermediate 4-d was synthesized according to Scheme 19 below.

<Reaction Scheme 19>

[중간체 4-c] [중간체 4-a] [중간체 4-d]

[Intermediate 4-c] [Intermediate 4-a] [Intermediate 4-d]

The same procedure was followed except that [Intermediate 4-c] was used instead of [Intermediate 1-a] in [Synthesis Example 1- (4) d]. (10 g, 70%)

Synthesis Example 4- (5): Synthesis of [Formula 58]

[Chemical Formula 58] was synthesized according to Reaction Scheme 20 below.

<Reaction Scheme 20>

[중간체 4-d] [화학식 58]

[Intermediate 4-d]

The same procedure was followed except that [Intermediate 4-d] was used instead of [Intermediate 1-d] in Synthesis Example 1- (5) to obtain [Formula 58]. (3.5 g, 34%).

MS (MALDI-TOF): m / z 1126.50 [M ^&lt; ⁺ &^gt;].

Synthesis Example 5: Synthesis of Compound (80)

Synthesis of Synthesis Example 5- (1): [Intermediate 5-a]

[Intermediate 5-a] was synthesized according to the following Reaction Scheme 21.

<Reaction Scheme 21>

                          [Intermediate 5-a]

The procedure of Synthesis Example 1- (2) was repeated except that 2-bromo-biphenyl was used instead of 1-bromo-2,5-dimethylbenzene to obtain Intermediate 5-a. (15 g, 60%).

Synthesis of Synthesis Example 5- (2): [Intermediate 5-b]

[Intermediate 5-b] was synthesized according to the following Reaction Scheme 22.

<Reaction Formula 22>

                                  [Intermediate 5-b]

2-Amino-5-bromobenzothiol (15.0 g, 73 mmol) and 1-naphthylaldehyde (10.3 g, 66 mmol) were dissolved in 1,4-dioxane in a 100 ml round- Lt; / RTI &gt; The mixture was extracted with dichloromethane, concentrated under reduced pressure, and then separated by column chromatography to obtain [intermediate 5-b]. (12.3 g, 49%).

Synthesis of Synthesis Example 5- (3): [Intermediate 5-c]

[Intermediate 5-c] was synthesized according to the following Reaction Scheme 23.

<Reaction Scheme 23>

       [Intermediate 5-a] [Intermediate 5-c]

The procedure of Intermediate 5-a was repeated except that Intermediate 5-a was used instead of Intermediate 1-b in Synthesis Example 1- (3). (13 g, 75%)

Synthesis of Synthesis Example 5- (4): [Intermediate 5-d]

[Intermediate 5-d] was synthesized according to the following Reaction Scheme 24.

<Reaction Scheme 24>

 [Intermediate 5-b] [Intermediate 5-c]       [Intermediate 5-d]

[Intermediate 5-c] was used instead of [Intermediate 5-b] instead of [Intermediate 1-a] in the above Synthesis Example 1- (4) d]. (11 g, 75%)

Synthesis of Synthesis Example 5- (5): [Formula 80]

[Formula 80] was synthesized according to Reaction Scheme 25 below.

<Reaction Scheme 25>

              [Intermediate 5-d] [Formula 80]

The same procedure was followed except that [Intermediate 5-d] was used instead of [Intermediate 1-d] in Synthesis Example 1- (5) to obtain [Formula 80]. (3.2 g, 28%).

MS (MALDI-TOF): m / z 1136.37 [M ^&lt; ⁺ &^gt;].

Synthesis Example 6: Synthesis of Formula 89

Synthesis of Synthesis Example 6- (1): [Intermediate 6-a]

[Intermediate 6-a] was synthesized according to the following Reaction Scheme 26.

<Reaction Scheme 26>

[중간체 6-a]

[Intermediate 6-a]

The procedure of Synthesis Example 1- (3) was repeated except that 4-methylbenzeneboronic acid was used instead of [Intermediate 1-b] to obtain [Intermediate 6-a]. (13 g, 75%)

Synthesis of Synthesis Example 6- (2): [Intermediate 6-b]

[Intermediate 6-b] was synthesized according to the following Reaction Scheme 27.

<Reaction Scheme 27>

[중간체 6-b]

[Intermediate 6-b]

In the same manner as in Synthesis Example 1- (1) except that 4-fluorobenzyl alcohol was used instead of benzyl alcohol, [Intermediate 6-b] was obtained. (13.0 g, 41%).

Synthesis of Synthesis Example 6- (3): [Intermediate 6-c]

Intermediate 6-c] was synthesized according to Reaction Scheme 28 below.

<Reaction Scheme 28>

                  [Intermediate 3-b] [Intermediate 6-c]

To a 2 L round bottom flask was added 1,6-dibromopyrene (70 g, 0.194 mol), [intermediate 3-b] (52.2 g, 0.428 mol), tetrakis (triphenylphosphine) palladium ), Potassium carbonate (80.6 g, 0.583 mol), toluene (350 ml), tetrahydrofuran (350 ml) and water (140 ml). After completion of the reaction, the solution is cooled to room temperature, and the resulting solid is filtered and washed with ethanol. The solid was dissolved in toluene, cooled at room temperature, and the resulting solid was filtered to obtain [intermediate 6-c]. (60.0 g, 87%)

Synthesis of Synthesis Example 6- (4): [Intermediate 6-d] Intermediate 6-d was synthesized according to Reaction Scheme 29 below.

<Reaction Scheme 29>

[Intermediate 6-c] [Intermediate 6-d]

[Intermediate 6-c] (30.0 g, 0.085 mol) was dissolved in 900 ml of dimethylformamide, and N-bromosuccinimide (33.1 g, 0.186 mol) was added to a 2 L round bottom flask, followed by stirring at 50 ° C for 8 hours . After completion of the reaction, 500 ml of water was added, and the resulting solid was filtered and washed with water and methanol. Dissolved in dichlorobenzene, cooled to room temperature, and the resulting solid was filtered to obtain [intermediate 6-d]. (30 g, 69%).

Synthesis of Synthesis Example 6- (5): [Intermediate 6-e]

[Intermediate 6-e] was synthesized according to the following Reaction Scheme 30.

<Reaction Scheme 30>

[Intermediate 6-a] [Intermediate 6-b] [Intermediate 6-e]

The procedure of Intermediate 6-a was repeated except that [Intermediate 6-b] was used instead of [Intermediate 1-a] in place of [Intermediate 6-a] in Synthesis Example 1- (4) e]. (11 g, 70%).

Synthesis Example 6- (6): Synthesis of [Formula 89]

[Formula 89] was synthesized according to Reaction Scheme 31 below.

<Reaction Scheme 31>

[Intermediate 6-d] [Intermediate 6-e]

The same procedure was followed except that [Intermediate 6-d] was used instead of 1,6-dibromopyrrene in Synthesis Example 1- (5), except that [Intermediate 6-e] was used instead of [Intermediate 1-d] (89). (3.3 g, 28%)

MS (MALDI-TOF): m / z 1168.43 [M ^&lt; ⁺ &^gt;].

Synthesis Example 7: Synthesis of Formula 105

Synthesis Example 7- (1): Synthesis of [Intermediate 7-a]

[Intermediate 7-a] was synthesized according to the following Reaction Scheme 32.

<Reaction equation 32>

                                    [Intermediate 7-a]

The procedure of Synthesis Example 1- (1) was repeated except that 2-nitro-3-chlorophenol was used instead of 2-bromo-6-nitrophenol to obtain Intermediate 7-a. (13.0 g, 30%).

Synthesis of Synthesis Example 7- (2): [Intermediate 7-b]

[Intermediate 7-b] was synthesized according to the following Reaction Scheme 33.

<Reaction Scheme 33>

           [Intermediate 7-a] [Intermediate 7-b]

To a 250 ml round bottom flask was added [intermediate 7-a] (10.0 g, 44 mmol), 4-aminobiphenyl (14.7, 87 mmol) tris (dibenzylideneacetone) palladium (1.99 g, 0.2 mmol), sodium tertiary butoxide (Dicyclohexylphosphino) -2 ', 4', 6'-triisopropylbiphenyl (2.08 g, 0.44 mmol) and toluene (100 ml) were added and the mixture was refluxed under nitrogen atmosphere for 3 hours . After extraction, it was separated by column chromatography and recrystallized from methanol to obtain [intermediate 7-b]. (11 g, 69%)

Synthesis Example 7- (3): Synthesis of [Formula 105]

[Chemical Formula 105] was synthesized according to the following Reaction Scheme 34.

<Reaction formula 34>

               [Intermediate 7-b]

The same procedure was followed except that [Intermediate 7-b] was used instead of [Intermediate 1-d] in Synthesis Example 1- (5) to obtain [Formula 105]. (2.7 g, 29%).

MS (MALDI-TOF): m / z 922.33 [M ^&lt; ⁺ &^gt;].

Synthesis Example 8: Synthesis of Formula 109

Synthesis Example 8- (1): Synthesis of [Intermediate 8-a]

[Intermediate 8-a] was synthesized according to the following Reaction Scheme 35.

<Reaction Scheme 35>

                                       [Intermediate 8-a]

An intermediate [8-a] was obtained in the same manner as in Synthesis Example 1- (4) except that benzeneamine was used in place of [Intermediate 1-c]. (9.3 g, 76%).

Synthesis Example 8- (2): Synthesis of [Intermediate 8-b]

[Intermediate 8-b] was synthesized according to the following Reaction Scheme 36.

<Reaction Formula 36>

             [Intermediate 8-a] [Intermediate 8-b]

(7.7 g, 27 mmol), 1,6-dibromopyrene (8.1 g, 22.5 mmol), 2,2'-bis (diphenylphosphino) -1-1'-binaphthyl (4.3 g, 45 mmol) and palladium acetate (0.1 g, 0.45 mmol) were added to 100 mL of toluene and refluxed for 24 hours. Extracted with ethyl acetate and washed with methanol. The resultant product was separated by column chromatography to obtain [Intermediate 8-b]. (4.9 g, 40%).

Synthesis Example 8- (3): Synthesis of [Formula 109]

[Chemical Formula 109] was synthesized according to the following Reaction Scheme 37.

(Reaction Scheme 37)

[Intermediate 8-b] [Intermediate 1-d]

The procedure of Synthesis Example 8- (2) was repeated except that [Intermediate 1-d] was used instead of [Intermediate 8-a] in place of 1,6-dibromopyrene to obtain [ ]. (3.5 g, 33%)

MS (MALDI-TOF): m / z 889.34 [M ^&lt; ⁺ &^gt;].

Synthesis Example 9: Synthesis of Formula 116

Synthesis Example 9- (1): Synthesis of [Intermediate 9-a]

[Intermediate 9-a] was synthesized according to the following Reaction Scheme 38.

<Reaction Formula 38>

       [Intermediate 5-b] [Intermediate 9-a]

Methylbenzenamine was used instead of [intermediate 1-a] instead of [intermediate 5-b] instead of [intermediate 1-c] in Synthesis Example 1- (4) ]. (10.1 g, 73%).

Synthesis Example 9- (2): Synthesis of [Intermediate 9-b]

[Intermediate 9-b] was synthesized according to the following Reaction Scheme 39.

<Reaction Scheme 39>

            [Intermediate 9-a] [Intermediate 9-b]

An intermediate 9-b was obtained in the same manner as in Synthesis Example 8- (2) except that [Intermediate 9-a] was used instead of [Intermediate 8-a]. (3.9 g, 37%).

Synthesis Example 9- (3): Synthesis of [Intermediate 9-c]

[Intermediate 9-c] was synthesized according to the following Reaction Scheme 40.

<Reaction formula 40>

   [Intermediate 6-b] [Intermediate 9-c]

Except that 5-methyl-2-pyridinamine was used instead of [intermediate 1-c] in the above Synthesis Example 1- (4), instead of [intermediate 6-b] 9-c]. (11.4 g, 74%)

Synthesis Example 9- (4): Synthesis of [Formula 116]

[Chemical Formula 116] was synthesized according to the following Reaction Scheme 41.

<Reaction Scheme 41>

[Intermediate 9-b] [Intermediate 9-c]

The procedure of Synthesis Example 8- (2) was repeated except that [Intermediate 9-b] was used instead of 1,6-dibromopyrene in place of [Intermediate 9-c] ]. (2.9 g, 30%).

MS (MALDI-TOF): m / z 883.28 [M ^&lt; ⁺ &^gt;

Example 1-7: Article of the organic EL device

The ITO glass was patterned to have a light emitting area of 2 mm x 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 then DNTPD (700 Å) and α-NPD (300 Å) a mixture of compound 3% due to the film formation (250Å), and then by film-forming in the order of _{Alq 3 (350 Å), LiF} (5 Å), Al (1000 Å) was prepared in the organic light emitting device. The luminescent characteristics of the organic light emitting device were measured at 0.4 mA.

            [DNTPD] [[alpha] -NPD]

[BH1] [Alq _3]

Comparative Examples 1 to 2

In the Examples 1 to 7, Except that [BD1] and [BD2] were used in place of the compound, and the emission characteristics of the organic light emitting device were measured at 0.4 mA. The structures of [BD1] and [BD2] are as follows.

         [BD1] [BD2]

The voltage, current, luminance, color coordinates, and lifetime of the organic light-emitting device manufactured according to Examples 1 to 7 and Comparative Examples 1 and 2 were measured, and the results are shown in Table 1 below. T80 means the time required for the luminance to be reduced to 80% of the initial luminance.

Voltage
(V) Current density
(mA / cm ² ) Luminance
(cd / m ² ) CIEx CIEy Quantum efficiency T80 Example 1
[Chemical Formula 1] 3.8 10 600 0.142 0.097 5.61 80 Example 2
[Chemical Formula 21] 3.8 10 633 0.141 0.110 5.77 95 Example 3
[Chemical Formula 39] 3.8 10 620 0.143 0.107 6.16 96 Example 4
(58) 3.7 10 610 0.140 0.099 6.09 85 Example 5
(80) 3.8 10 578 0.141 0.105 6.83 100 Example 6
(89) 3.7 10 717 0.142 0.124 5.43 75 Example 7
&Lt; EMI ID = 3.7 10 752 0.141 0.120 6.46 110 Comparative Example 1
[BD1] 6.4 10 515 0.143 0.160 4.96 42 Comparative Example 2
[BD2] 6.0 10 550 0.141 0.168 4.88 40

As shown in Table 1, the asymmetric pyrene derivative according to the present invention has far superior luminance and luminescent efficiency than the compound of Comparative Example 1 and Comparative Example 2, and exhibits excellent device characteristics with a long life , And it is highly likely to be applied as an organic light emitting element.

Claims (16)

A pyrene derivative represented by the following formula (A).
(A)

In the above formula (A)
X is one selected from O, S and Se,
The linking groups L ₁ and L ₂ are the same or different and independently of one another are a single bond, a substituted or unsubstituted arylene group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroatom selected from O, N, S and Si Or a heteroarylene group having 2 to 50 carbon atoms,
Ar ₁ and Ar ₂ are the same or different and independently of each other, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, or a substituted or unsubstituted heteroatom selected from O, N, S and Si A heteroaryl group having 2 to 50 carbon atoms,
Each substituent M which is bonded to the nitrogen atom of the amine group may be the same or different,
Wherein _one of R ₁ to R ₄ in the substituent M is a single bond bonded to a nitrogen atom,
R ₁ to R ₅ are the same or different from each other and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, Substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkyl, An alkenyl group, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having at least one heteroatom selected from O, N, S and Si, 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 alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, A substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, An amino group, an amino group, an amino group, an amino group, an amino group, an amino group, a nitro group, a halogen group,
Each carbon atom in the pyrene ring is bonded to the nitrogen atom of the amine or, when not bonded to the substituent Z, to hydrogen;
m is an integer of 1 to 8, and when m is 2 or more, each Z is the same or different from each other,
p and q are the same or different integers of 1 to 3, and when p is 2 or more, each Ar ₁ is the same or different, and when q is 2 or more, each Ar ₂ is the same or different,
The 'substituted' in the above 'substituted or unsubstituted' means a group selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, , An alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms , An alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, Group, and an aryloxy group having 1 to 24 carbon atoms. The method according to claim 1,
Wherein when Ar ₁ and Ar ₂ are the same or different and each is a heteroaryl group, the heteroaryl group is any one selected from the following Substituents 101 to 117:
[Substituent 101] [Substituent 102] [Substituent 103] [Substituent 104]

[Substituent group 105] [Substituent group 106] [Substituent group 107]

[Substituent group 108] [Substituent group 109] [Substituent group 110]

[Substituent group 111] [Substituent group 112] [Substituent group 113]

[Substituent group 114] [Substituent group 115] [Substituent group 116]

[Substituent group 117]

Wherein R is the same or different and is independently selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted alkylthio 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 6 to 50 carbon atoms, a substituted or unsubstituted arylthio group having 1 to 30 carbon atoms, Or a substituted or unsubstituted aryloxy group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, (Substituted or unsubstituted alkyl group having 1 to 30 carbon atoms), a di (substituted or unsubstituted C1 to C30 alkyl) amino group, a substituted or unsubstituted C6 to C30 arylamino group, a substituted or unsubstituted An aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, germanium, phosphorus, and boron, Substituents may be bonded to adjacent groups to form a saturated or unsaturated ring,
n is an integer of 1 to 9,
When the substituent R is not bonded to the carbon in the aromatic ring or the saturated hydrocarbon ring in the above [substituent groups 101] to [substituent group 117], hydrogen is bonded,
When the substituent R is 2 or more, each R may be the same or different from each other,
One of the substituents R in the above [substituent groups 101] to [substituent group 117] is a single bond which binds to the linking group L ₁ or L ₂ in the above formula (A)
The 'substitution' in the 'substituted or unsubstituted' is the same as defined in claim 1. The method according to claim 1,
Wherein when Ar ₁ and Ar ₂ are the same or different aryl groups, the aryl group is any one selected from the following [substituent group 201] to [substituent group 210]
[Substituent group 201] [Substituent group 202] [Substituent group 203]

[Substituent group 204] [Substituent group 205] [Substituent group 206]

[Substituent group 207] [Substituent group 208] [Substituent group 209]

[Substituent 210]

Wherein n is an integer of 1 to 9,
When the substituent R is not bonded to the carbon in the aromatic ring in the above [substituent 201] to [substituent 210], hydrogen is bonded,
The substituent R is the same as the definition of the substituent R in the above-mentioned 2. The method according to claim 1,
Wherein each of the linking groups L1 and L2 is a single bond or is any one selected from the following Structural Formulas 101 to 210:
[Structural Formula 101] [Structural Formula 102] [Structural Formula 103] [Structural Formula 104]

[Structural Formula 105] [Structural Formula 106] [Structural Formula 107]

[Structural Formula 108] [Structural Formula 109] [Structural Formula 110]

[Structural Formula 111] [Structural Formula 112] [Structural Formula 113]

[Structural Formula 114] [Structural Formula 115] [Structural Formula 116]

[Structural Formula 117]

[Structural Formula 201] [Structural Formula 202] [Structural Formula 203]

[Structural Formula 204] [Structural Formula 205] [Structural Formula 206]

[Structural Formula 207] [Structural Formula 208] [Structural Formula 209]

[Structural Formula 210]

Wherein n is an integer from 2 to 9,
In the case where the substituent R is not bonded to the aromatic ring or the carbon in the saturated hydrocarbon ring in the above structural formulas 101 to 210,
Two to four R's of the substituents R included in the above Structural Formulas 101 to 210 are respectively a single bond bonded to the nitrogen atom and the substituent Ar ₁ or a single bond bonded to the nitrogen atom and the substituent Ar ₂ ,
The substituent R is the same as defined in claim 2. The method according to claim 1,
The substituent Z is any one selected from the group consisting of deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms Characterized in that the pyrene derivative. 6. The method according to any one of claims 1 to 5,
Wherein the pyrene derivative of the formula (A) has amines bonded at positions 1, 6 or 2,7 respectively. 6. The method according to any one of claims 1 to 5,
Wherein M or Ar ₁ or Ar ₂ bonded to the amine of the above formula (A) contains deuterium. 6. The method according to any one of claims 1 to 5,
The substituent which is substituted in M, L ₁ , L ₂ , Ar ₁ and Ar ₂ is a cyano group, a halogen group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 18 carbon atoms, an arylalkyl group having 6 to 18 carbon atoms , A heteroaryl group having 3 to 18 carbon atoms, an alkylsilyl group having 1 to 12 carbon atoms, and an arylsilyl group having 6 to 18 carbon atoms. 6. The method according to any one of claims 1 to 5,
Wherein the pyrene derivative has the same two amine groups. 6. The method according to any one of claims 1 to 5,
Wherein the pyrene derivative is asymmetric with the two amine groups being different from each other. The method according to claim 1,
Is any one selected from the following [compound 1] to [compound 117].
[Compound 1] [Compound 2] [Compound 3]

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[Compound 85] [Compound 86] [Compound 87]

[Compound 88] [Compound 89] [Compound 90]

[Compound 91] [Compound 92] [Compound 93]

[Compound 94] [Compound 95] [Compound 96]

[Compound 97] [Compound 98] [Compound 99]

[Compound 100] [Compound 101] [Compound 102]

[Compound 103] [Compound 104] [Compound 105]

[Compound 106] [Compound 107] [Compound 108]

[Compound 109] [Compound 110] [Compound 111]

[Compound 112] [Compound 113] [Compound 114]

[Compound 115] [Compound 116] [Compound 117]

A first electrode;
A second electrode facing the first electrode; And
And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises at least one organic electroluminescent compound selected from the group consisting of organic electroluminescent compounds selected from the group consisting of the organic electroluminescent compounds of any one of claims 1 to 5, device. 13. The method of claim 12,
Wherein the organic layer comprises at least one of a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a light emitting layer, an electron transporting layer, and an electron injecting layer. 13. The method of claim 12,
An organic layer interposed between the first electrode and the second electrode includes a light emitting layer,
Wherein the light emitting layer comprises a host and a dopant, and the organic light emitting compound is used as a dopant. 14. The method of claim 13,
Wherein at least one layer selected from the respective layers is formed by a deposition process or a solution process. 13. The method of claim 12,
The organic light emitting device includes a flat panel display device; A flexible display device; Monochrome or white flat panel illumination devices; And a device for flexible illumination of a single color or a white color.

Images