KR102080738B1 - Pyrene derivatives and organic electro luminescent device comprising same - Google Patents

Abstract

The present invention relates to a pyrene derivative compound having an asymmetric structure and an organic light emitting device comprising the same as an organic light emitting compound, the pyrene derivative according to the invention is characterized in that represented by the following [Formula A] to [Formula B] In addition, the pyrene derivative compound according to the present invention exhibits a significantly improved blue color purity compared to the organic light emitting device employing the conventional pyrene-based arylamine derivative compound, and at the same time excellent in life characteristics, brightness characteristics can be implemented in full color, various It can be used as a display element.
[Formula A] [Formula B]

Description

Pyrene derivatives and organic light emitting devices comprising the same {PYRENE DERIVATIVES AND ORGANIC ELECTRO LUMINESCENT DEVICE COMPRISING SAME}

The present invention relates to a pyrene derivative compound having an asymmetric structure and an organic light emitting device comprising the same as an organic light emitting compound.

The material used as the organic material layer in the organic light emitting device may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function. The light emitting materials include blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize better natural colors, depending on the light emission color.

In addition, in order to increase luminous efficiency through increase in color purity and energy transfer, a host / dopant system may be used as the light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap than the host mainly constituting the light emitting layer and excellent luminous efficiency is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to produce high efficiency light. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

However, in order to fully exhibit the excellent characteristics of the above-described organic light emitting device, a material constituting the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. Although support should be preceded, development of a stable and efficient organic material layer for an organic light emitting device has not been sufficiently achieved, and therefore, development of new materials is continuously required.

Particularly, in order to realize full-color, it is necessary to arrange pixels displaying three primary colors of green, red, and blue on the panel. To emit light of green and red light by arranging the organic light emitting elements of the light emitting diode or by separating the light emitted from the light emitting element having white light emission into three primary colors through a color filter, or by using the light emission from the organic light emitting element that exhibits blue light emission as a light emitting source. A method of converting and the like has been proposed. In any case, blue light emission is essential, and there is an urgent need for a blue light emitting material having high brightness, high efficiency, and high color purity.

In the prior art, an organic electroluminescent device using a pyrene-based compound substituted with a diphenyl amine derivative is disclosed in Korean Patent No. 525408, but because of the low color purity, it is difficult to realize a dark blue color. I'm having trouble implementing On the other hand, US Patent No. US5153073 discloses an electroluminescent device using a pyrene-based compound substituted with a diphenyl amine derivative, but there is a disadvantage that the color purity of the filter battery blue is low and the luminance is very low. In addition, WO 2004/083162 discloses an organic electroluminescent device using a pyrene-based compound substituted with a diphenyl amine derivative. However, since the color purity of blue is low, it is difficult to realize a dark blue color. There is a problem with the implementation.

Accordingly, the present invention is to provide an organic light emitting device having a blue color purity by using a novel pyrene derivative compound as an organic light emitting compound, and at the same time having a light emission characteristics such as improved brightness, long life, low voltage driving.

The present invention provides a pyrene derivative compound having an asymmetric structure, which is represented by the following [Formula A] or [Formula B] in order to solve the above problems, characterized in that the two amine groups bonded to the pyrene are different from each other and have an asymmetric structure. do.

[Formula A] [Formula B]

In addition, the present invention provides an organic electroluminescent device having an anode, a cathode, and an organic material layer interposed between the anode and the cathode and including a pyrene derivative compound represented by the above [Formula A] or [Formula B].

Specific substituents of the above [Formula A] or [Formula B] will be described later.

The pyrene derivative compound according to the present invention exhibits a significantly improved blue color purity compared to the organic light emitting device employing the conventional pyrene-based arylamine derivative compound, and at the same time, it is possible to realize full color due to its excellent life characteristics and luminance characteristics. It can be used as an element.

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

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

The present invention relates to an asymmetric pyrene derivative compound represented by the following [Formula A] to [Formula B], the following pyrene derivative compound is a pyridinyl group wherein at least one substituted or unsubstituted each of the two amine groups bonded to the pyrene or A substituted or unsubstituted 6-membered aromatic heteroaryl group, wherein the 6-membered ring includes a heteroaryl group having two nitrogen atoms and the remaining carbon atoms, and two amine groups bonded to pyrene have different structures from each other. It is characterized by an asymmetrical structure.

As such, a pyridinyl group or a 6-membered aromatic heteroaryl group as a substituent on the amine group is a heteroaryl group having two nitrogen atoms and the remaining carbon atoms bonded to the six-membered ring, and two amine groups are asymmetric. The pyrene derivative of the present invention can improve the blue color purity of the device than the conventional organic light emitting material and can show an excellent device characteristics of high brightness can implement an organic light emitting device having improved light emission characteristics.

[Formula A] [Formula B]

In [Formula A] to [Formula B],

Py is a substituted or unsubstituted pyridinyl group or a substituted or unsubstituted 6-membered aromatic heteroaryl group, wherein the 6-membered ring may be a heteroaryl group having two nitrogen atoms and the remaining carbon atoms, and more specifically, May be pyridazine, pyrimidine, pyrazine and the like.

In addition, when Py is a pyridinyl group, the position of nitrogen contained in the pyridinyl group may have positions of ortho, meta, and para based on the position of nitrogen of the amine. That is, the nitrogen atom of the pyridinyl group and the amine may be bonded to be represented by the structure of [1] to [3].

[1] [2] [3]

In addition, when the Py is a heteroaryl group such as pyridazine, pyrimidine, pyrazine, respectively, the position of nitrogen contained in Py is any one selected from the following [4] to [9] based on the position of nitrogen of the amine. Can be combined to be represented in a structure.

[4] [5] [6]

[7] [8] [9]

Ar ₁ To Ar ₃ are the same as or different from each other, and each independently, 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 having 5 to 50 carbon atoms It may be selected from heteroaryl groups having 2 to 50 carbon atoms and substituted or unsubstituted and having any one or more selected from O, N, S, P and Si as heteroatoms.

L may be selected from a substituted or unsubstituted aryl group having 5 to 50 carbon atoms and a heteroaryl group having 2 to 50 carbon atoms having any one or more selected from O, N, S, P, and Si as a substituted or unsubstituted hetero atom. Can be. In addition, n is an integer of 1 to 3, and when n is 2 or more, the plurality of Ls may be the same or different from each other.

Z is hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 50 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon atoms Alkynyl groups of 2 to 20, substituted or unsubstituted cycloalkyl groups of 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl groups of 5 to 30 carbon atoms, substituted or unsubstituted heteroatoms O, N, S, P and Si A heteroaryl group having 2 to 50 carbon atoms having at least one selected from, 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 carbon number Alkylthioxy group having 1 to 30, substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, substituted or unsubstituted aryl having 5 to 30 carbon atoms It may be selected from a min group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group, a nitro group and a halogen group, m being 1 to 8 In the case where m is 2 or more, a plurality of Z's may be the same as or different from each other, and a plurality of Z's may be combined with each other or adjacent substituents to form a saturated or unsaturated ring.

In addition, in each of the carbon atoms in the pyrene ring of [Formula A] to [Formula B], a nitrogen atom of the amine or a carbon atom not bonded to a plurality of Z may be bonded to hydrogen.

According to a preferred embodiment of the present invention, the two amine groups in [Formula A] to [Formula B] may be bonded to the pyrene derivative 1, 6 position or 2, 7 position, respectively.

In addition, in the 'substituted or unsubstituted', 'substituted' means the Py, Ar ₁ To Ar ₃ , L and Z are each independently substituted with a substituent, the substituent is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group of 1 to 24 carbon atoms, halogenated of 1 to 24 carbon atoms Alkyl group, C1-C24 alkenyl group, C1-C24 alkynyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C6-C24 arylalkyl group, C2-C24 heteroaryl group 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 heteroarylaryl group having 1 to 24 carbon atoms, or an alkylsilyl having 1 to 24 carbon atoms It may be at least one selected from the group consisting of a group, an arylsilyl group having 1 to 24 carbon atoms and an aryloxy group having 1 to 24 carbon atoms.

According to a preferred embodiment of the present invention, at least one selected from Ar ₁ to Ar ₃ bonded to the amines of [Formula A] to [Formula B], or the Py is characterized in that it contains deuterium, The substituents substituted for Py and Ar ₁ to Ar ₃ are more specifically cyano groups, halogen groups, alkyl groups having 1 to 6 carbon atoms, aryl groups having 6 to 18 carbon atoms, arylalkyl groups having 6 to 18 carbon atoms, and 3 to 18 carbon atoms. It may be at least one selected from the group consisting of a heteroaryl group, an alkylsilyl group having 1 to 12 carbon atoms, an arylsilyl group having 6 to 18 carbon atoms.

In addition, according to a preferred embodiment of the present invention, Ar ₁ When Ar to ₃ are each a heteroaryl group, the heteroaryl group may be selected from the following [formula A] to [formula F].

[Structure A] [Structure B] [Structure C] [Structure D]

[Structure E] [Structure F]

In [Formula A] to [Formula F], each includes at least one nitrogen atom, sulfur atom, oxygen atom, phosphorus atom or silicon atom.

In addition, T ₁ to T ₈ are the same as or different from each other, and each independently, any one selected from C (R ₁₁ ), C (R ₁₁ ) (R ₁₂ ), N, N (R ₁₃ ), O and S When C (R ₁₁ ), C (R ₁₁ ) (R ₁₂ ) and N (R ₁₃ ) any one of the plurality in the [formula A] to [formula F] included in the plurality of Each C (R ₁₁ ), C (R ₁₁ ) (R ₁₂ ) and N (R ₁₃ ) may be the same or different from each other.

In addition, R ₁ to R ₁₃ Are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted cyclo group having 3 to 30 carbon atoms An alkyl group and a substituted or unsubstituted heteroaryl group having 2 or 50 carbon atoms having at least one selected from O, N, S, P, and Si, and R ₁ One to R ₁₃ to form a single bond with the nitrogen atom bonded to the pyrene of [Formula A] and [Formula B].

In addition, when the T ₁ to T ₈ and R ₁ to R ₁₃ are each independently further substituted with a substituent, the substituent is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 24 carbon atoms, carbon number 1 A halogenated alkyl group having 24 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, and having 2 to 2 carbon atoms 24 heteroaryl group or C2-C24 heteroarylalkyl group, C1-C24 alkoxy group, C1-C24 alkylamino group, C1-C24 arylamino group, C1-C24 heteroarylaryl group, C1-C24 It may be at least one selected from the group consisting of an alkylsilyl group having from 24 to 24, an arylsilyl group having 1 to 24 carbon atoms, and an aryloxy group having 1 to 24 carbon atoms.

As above, Ar ₁ When Ar ₃ to each heteroaryl group, according to a preferred embodiment, Ar ₁ Ar ₃ to each independently may be any one selected from [substituent 101] to [substituent 612].

[Substitution 101] [Substitution 102] [Substitution 103]

[Substitution 104] [Substitution 105] [Substitution 106]

[Substituent 107] [Substituent 108]

[Substitution 109] [Substitution 110] [Substitution 111]

[Substitution 112] [Substitution 113] [Substitution 114] [Substitution 115]

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

[Substituent 204] [Substituent 205]

[Substituent 301] [Substituent 302] [Substituent 303]

[Substituent 304] [Substituent 305] [Substituent 306]

[Substitution 307] [Substitution 308] [Substitution 309] [Substitution 310]

[Substituent 401] [Substituent 402] [Substituent 403]

[Substituent 404] [Substituent 405] [Substituent 406]

[Substituent 407] [Substituent 408] [Substituent 409]

[Substituent 410] [Substituent 411] [Substituent 412] [Substituent 413]

[Substituent 501] [Substituent 502] [Substituent 503] [Substituent 504]

[Substituent 505] [Substituent 506] [Substituent 507]

[Substituent 601] [Substituent 602] [Substituent 603]

[Substituent 604] [Substituent 605] [Substituent 606]

[Substituent 607] [Substituent 608] [Substituent 609]

[Substituent 610] [Substituent 611] [Substituent 612]

In the [substituent 101] to [substituent 612],

R is hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted An alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, substituted or unsubstituted Substituted alkylthio group having 1 to 60 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, substituted or unsubstituted aryl group having 6 to 60 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, Substituted or unsubstituted arylthio groups having 5 to 60 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms, substituted or unsubstituted (alkyl) amino groups having 1 to 60 carbon atoms, di (substituted or Unsubstituted C1-C60 alkyl) amino group, or (substituted or unsubstituted C6-C60 aryl) amino group, di (substituted or unsubstituted C6-C60 aryl) amino group, substituted or unsubstituted carbon number It may be selected from an alkylsilyl group having 1 to 40, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus and boron.

n is an integer of 1 to 9, when n is 2 or more, a plurality of R may be identical to or different from each other, and may be fused with adjacent substituents to form a ring.

In addition, one of the plurality of R is bonded to the nitrogen atom of the amine bonded to the pyrene of [Formula A] to [Formula B] to form a single bond, hetero represented by [substituent 101] to [substituent 612] Hydrogen is bonded to the carbon to which R is not bonded in the carbon of the aromatic ring in the aryl group.

In addition, when R is further substituted with a substituent, the substituent is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group of 1 to 24 carbon atoms, halogenated alkyl group of 1 to 24 carbon atoms, alke of 1 to 24 carbon atoms An alkyl 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, or a heteroaryl having 2 to 24 carbon atoms Alkyl group, C1-C24 alkoxy group, C1-C24 alkylamino group, C1-C24 arylamino group, C1-C24 hetero arylamino group, C1-C24 alkylsilyl group, C1-C24 aryl It may be at least one selected from the group consisting of a silyl group and an aryloxy group having 1 to 24 carbon atoms.

The pyrene derivative having an asymmetric structure represented by [Formula A] of the present invention may be more specifically any one selected from the following [Formula A-1] to [Formula A-5].

[Formula A-1] [Formula A-2] [Formula A-3]

[Formula A-4] [Formula A-5]

In [Formula A-1] to [Formula A-5],

Ar ₁₁ , Ar ₂₁ and Ar ₃₁ may be the same as or different from each other, and may each independently be a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, and Het ₁ , Het ₂ and Het ₃ may be the same or different from each other, and each independently It may be a heteroaryl group having 2 to 50 carbon atoms substituted or unsubstituted and having any one or more selected from O, N, S, P and Si as a hetero atom.

L, Z, m and n are the same as the definition in [Formula A].

In addition, the pyrene derivative of the asymmetric structure represented by [Formula B] of the present invention may be any one selected from the following [Formula B-1] to [Formula B-5].

[Formula B-1] [Formula B-2] [Formula B-3]

[Formula B-4] [Formula B-5]

In [Formula B-1] to [Formula B-5],

Ar ₁₁ , Ar ₂₁ and Ar ₃₁ may be the same as or different from each other, and may each independently be a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, and Het ₁ , Het ₂ and Het ₃ may be the same or different from each other, and each independently It may be a heteroaryl group having 2 to 50 carbon atoms substituted or unsubstituted and having any one or more selected from O, N, S, P and Si as a hetero atom.

L, Z, m and n are the same as the definition in [Formula B].

In addition, according to a preferred embodiment of the present invention, Z is deuterium, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted C 3 to 30 It may be any one selected from a cycloalkyl group and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In addition, Het ₁ to Het ₃ are each independently the following [substituent 101], [substituent 201], [substituent 402], [substituent 403], [substituent 406], [substituent 407], [substituent 409], [substituent 502], [substituent 503], [substituent 504], [substituent 601] and [substituent 602], and Ar ₁₁ to Ar ₃₁ are each independently the following [substituent 801] to [substituent 809 ] May be any one selected from.

[Substituent 101] [substituent 201] [substituent 402]

[Substituent 403] [Substituent 406] [Substituent 407]

[Substituent 409] [Substituent 502] [Substituent 503] [Substituent 504]

[Substituent 505] [Substituent 601] [Substituent 602]

[Substituent 801] [Substituent 802] [Substituent 803]

[Substituent 804] [Substituent 805] [Substituent 806]

[Substituent 807] [Substituent 808] [Substituent 809]

Wherein R, R 'and R "are the same as defined above.

The present invention also includes 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 is represented by [Formula A] to [Formula B]. It may contain one or more pyrene derivatives represented by.

In addition, the organic layer including the pyrene derivative compound of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time, a light emitting layer, an electron transport layer, and an electron injection layer. have. In this case, the organic layer interposed between the first electrode and the second electrode may include a light emitting layer, the light emitting layer is composed of a host and a dopant, the pyrene derivative compound of the present invention may be used as a dopant.

Meanwhile, in the present invention, the light emitting layer includes a host material together with the compound represented by [Formula A] to [Formula B] according to the present invention, and the content of the pyrene derivative compound of the present invention, that is, the dopant in the light emitting layer is typically And from about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host.

In addition, as the electron transporting material in the present invention, a known electron transporting material may be used as a function of stably transporting electrons injected from an electron injection electrode (Cathode). Examples of known electron transport materials include quinoline derivatives, in particular tris (8-quinolinorate) aluminum (Alq 3), TAZ, Balq, beryllium bis (benzoquinolin-10-noate) olate: Bebq2), ADN, [Compound 201], [Compound 202], oxadiazole derivatives such as PBD, BMD, BND or the like may be used.

TAZ BAlq

[Compound 201] [Compound 202] BCP

In addition, in the electron transporting layer used in the present invention, an organometallic compound represented by the following [Formula C] may be used alone or in combination with the electron transporting layer material.

[Formula C]

In [Formula C],

Y is a portion in which any one selected from C, N, O and S is directly bonded to M to form a single bond, and any one selected from C, N, O and S forms a coordination bond to M. And a ligand chelated by the single bond and the coordinating bond.

M is an alkali metal, alkaline earth metal, aluminum (Al) or boron (B) atom.

OA is a monovalent ligand capable of single bond or coordination with M, wherein O is oxygen, and A is 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 alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl having 5 to 30 carbon atoms Alkenyl group and substituted or unsubstituted, heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom.

In addition, when M is one metal selected from alkali metals, m = 1, n = 0, and when M is one metal selected from alkaline earth metals, m = 1, n = 1, or m = 2, n = 0, and when M is boron or aluminum, any one of m = 1 to 3, n is any of 0 to 2 to satisfy m + n = 3.

The 'substituted' in the 'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group, alkoxy group, alkylamino group, arylamino group, hetero arylamino group, alkylsilyl group, arylsilyl group, It is meant to be substituted with one or more substituents selected from the group consisting of an aryloxy group, an aryl group, a heteroaryl group, germanium, phosphorus and boron.

In addition, the Y may be the same or different from each other, and may be any one selected from the following [formula C1] to [formula C39].

[Structure C1] [Structure C2] [Structure C3]

[Structure C4] [Structure C5] [Structure C6]

[Structure C7] [Structure C8] [Structure C9] [Structure C10]

[Formula C11] [Formula C12] [Formula C13]

[Formula C14] [Formula C15] [Formula C16]

[Structure C17] [Structure C18] [Structure C19] [Structure C20]

[Structure C21] [Structure C22] [Structure C23]

[Structure C24] [Structure C25] [Structure C26]

[Structure C27] [Structure C28] [Structure C29] [Structure C30]

[Structure C31] [Structure C32] [Structure C33]

[Structure C34] [Structure C35] [Structure C36]

[Structure C37] [Structure C38] [Structure C39]

In [Formula C1] to [Formula C39],

R is the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted Heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or Unsubstituted C1-C30 alkylamino group, substituted or unsubstituted C1-C30 alkylsilyl group, substituted or unsubstituted C6-C30 arylamino group, and substituted or unsubstituted C6-C30 arylsilyl Selected from the group, and may be connected to adjacent substituents with alkylene or alkenylene to form a spirogory or fused ring.

L is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon group having 5 to 30 carbon atoms A heteroaryl group and a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, L is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, and 3 to 20 carbon atoms Is further substituted with one or more substituents selected from a heteroaryl group, a cyano group, a halogen group, deuterium and hydrogen, and may be connected to an adjacent substituent with alkylene or alkenylene to form a spirogory or fused ring.

Hereinafter, the organic light emitting display device of the present invention will be described with reference to FIG. 1.

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

Referring to Figure 1 with respect to the organic light emitting device of the present invention and a method of manufacturing the same.

First, the anode 20 is formed by coating an anode electrode material on the substrate 10. As the substrate 10, a substrate used in a conventional organic EL device is used. An organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness is preferable. As the anode electrode material, transparent indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and the like are used.

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

The hole injection layer material may be used without particular limitation as long as it is commonly used in the art, for example, 2-TNATA [4,4 ', 4 "-tris (2-naphthylphenyl-phenylamino) -triphenylamine] , NPD [N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine)], TPD [N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'- biphenyl-4,4'-diamine], DNTPD [N, N'-diphenyl-N, N'-bis- [4- (phenyl-m-tolyl-amino) -phenyl] -biphenyl-4,4'-diamine ] Can be used.

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

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

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

In addition, the light emitting layer may include a host and a dopant compound represented by [Formula A] or [Formula B] according to the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 kPa.

In this case, the host used in the emission layer may be a compound represented by the following [Formula 1A] to [Formula 1D].

[Formula 1A]

In [Formula 1A],

Ar _{7 ,} Ar ₈ and Ar ₉ are the same as or different from each other, and each independently, a single bond, a substituted or unsubstituted C ₅ -C ₆₀ aromatic linking group, or a substituted or unsubstituted C ₂ -C ₆₀ It may be a heteroaromatic linking group.

R ₂₁ to R ₃₀ are the same as or different from each other, and each independently 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 carboxyl group or a salt thereof, a sulfonic acid group or Salts thereof, phosphoric acid or salts thereof, substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 60 carbon atoms, substituted or unsubstituted Substituted alkoxy group having 1 to 60 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, substituted or unsubstituted aryl having 6 to 60 carbon atoms A group, 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, Substituted or unsubstituted (alkyl) amino group having 1 to 60 carbon atoms, di (substituted or unsubstituted alkyl group having 1 to 60 carbon atoms), or (substituted or unsubstituted aryl having 6 to 60 carbon atoms), di (substituted Or an unsubstituted aryl) amino group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus and boron. And each substituent may form a condensed ring with a group adjacent to each other.

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

The two sites represented by * of the anthracene may be the same or different from each other, and each independently combine with the P or Q structure to constitute an anthracene-based derivative selected from the following [Formula 1Aa-1] to [Formula 1Aa-3] can do.

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

Here, the 'substituted' in the 'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group of 1 to 24 carbon atoms, halogenated alkyl group of 1 to 24 carbon atoms, of 1 to 24 carbon atoms Alkenyl group, C1-C24 alkynyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C6-C24 arylalkyl group, C2-C24 heteroaryl group, or C2-C24 hetero Arylalkyl group, a C1-C24 alkoxy group, C1-C24 alkylamino group, C1-C24 arylamino group, C1-C24 hetero arylamino group, C1-C24 alkylsilyl group, C1-C24 It means that it is substituted with one or more substituents selected from the group consisting of an arylsilyl group, an aryloxy group having 1 to 24 carbon atoms.

[Formula 1B]

In [Formula 1B],

Ar ₁₇ to Ar ₂₀ may be the same as or different from each other, and each independently the same substituent as defined in Ar ₇ to Ar ₈ in Formula 1A, and R ₆₀ to R ₆₃ may be defined in R ₂₁ to R ₃₀ of Formula 1A. And the same substituent as described above.

The w and ww are the same or different from each other, the x and xx are the same or different from each other, the w + ww and x + xx values are the same or different from each other and are each independently an integer of 0-3. In addition, y and yy are the same as or different from each other, z and zz are the same as or different from each other, and y + yy to z + zz are 2 or less, and are integers of 0 to 2, respectively.

[Formula 1C]

In [Formula 1C],

Ar ₂₁ to Ar ₂₄ may be the same as or different from each other, and each independently the same substituent as defined in Ar ₇ to Ar ₈ of Formula 1A, and R ₆₄ to R ₆₇ may be selected from R ₂₁ to R ₃₀ of Formula 1A. It consists of the same substituent as defined.

In addition, ee to hh are the same as or different from each other, and each independently an integer of 1 to 4, and ii to ll are the same or different from each other, and each independently an integer of 0 to 4.

[Formula 1D]

In [Formula 1D],

Ar ₂₅ to Ar ₂₇ are the same as or different from each other, and each independently include the same substituent as defined in Ar ₇ to Ar ₈ of Formula 1A, and R ₆₈ to R ₇₃ are the same as or different from each other, and each independently It consists of the same substituent as defined in R <_21> -R <_30> of 1A, and each substituent may form a saturated or unsaturated cyclic structure with adjacent ones. In addition, the mm to ss are the same as or different from each other and are each independently an integer of 0 to 4.

More specifically, the host may be represented by any one selected from the group represented by 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]

[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]

In addition, one or more layers selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer may be formed by a single molecule deposition method or a solution process, wherein the deposition method Means a method of forming a thin film by evaporating a material used as a material for forming each layer through heating or the like in a vacuum or low pressure state, and the solution process is used as a material for forming each layer. It refers to a method of forming a thin film through a method such as mixing the material with a solvent and inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating and the like.

Further, the organic light emitting display device according to the present invention can be used in a device selected from a flat panel display device, a flexible display device, a flat or white flat illumination device and a single or white flexible illumination device.

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

Synthesis Example 1. Synthesis of [Compound 1]

Synthesis of [Intermediate 1-a]

[Intermediate 1-a]

1-cyano-4-chlorobenzene (13.8 g, 0.1 mol), 2-methyl-5-aminopyridine (10.8 g, 0.1 mol), palladium acetate (0.08 g, 0.32 mmol), 2,2'-bis ( Diphenylphosphino) -1-1'-binapryl (0.26 g, 0.42 mmol) and sodium tert-butoxide (15.2 g, 0.16 mol) were added to 150 mL of toluene and refluxed for 12 hours. After cooling to room temperature, the mixture was washed with methanol and recrystallized with dichloromethane and methanol to obtain 15.3 g [Intermediate 1-a] (yield 73%).

Synthesis of [Intermediate 1-b]

[Intermediate 1-b]

[Intermediate 1-a] (5.6 g, 27 mmol), 1,6-dibromopyrene (8.1 g, 22.5 mmol), and 2,2'-bis (diphenylphosphino) synthesized in the above [Scheme 1-1] ) -1-1'-binaphthyl (0.28 g, 0.45 mmol), sodium tertiary review side (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. I was. Extracted with ethyl acetate and washed with methanol. Separation by column chromatography gave 4.8 g (44% yield) of [Intermediate 1-b].

[Scheme 1-3] Synthesis of [Intermediate 1-c]

[Intermediate 1-c]

Instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], pentadutereobromobenzene was used, and 1-amino-4-methylbenzene was used instead of 2-methyl-5-aminopyridine. [Intermediate 1-c] (yield 75%) was obtained by the method.

[Scheme 1-4] Synthesis of [Intermediate 1-d]

[Intermediate 1-d]

Instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], 4-bromophenylboronic acid was used, and instead of 2-methyl-5-aminopyridine, [ [Intermediate 1-d] (yield 77%) was obtained by the same method using Intermediate 1-c].

[Scheme 1-5] Synthesis of [Compound 1]

[Compound 1]

[Intermediate 1-d] (24 g, 0.073 mol), [Intermediate 1-b] (29.8 g, 0.061 mol) synthesized in the above [Scheme 1-4], Tetrakis (triphenylphosphine) palladium (3.62 g , 0.003 mol) and potassium carbonate (16.9 g, 0.122 mol) were added to 150 mL of 1,4-dioxane, 150 mL of toluene, and 60 mL of distilled water, and refluxed for 12 hours. Cooled to room temperature, extracted with ethyl acetate and separated by column chromatography to give 23.6 g (56%) of [Compound 1].

MS (MALDI-TOF): m / z 670.30 [M] ⁺

Synthesis Example 2. Synthesis of [Compound 2]

Synthesis of [Intermediate 2-a]

[Intermediate 2-a]

2-chloro-4,6-dimethylpyridine is used instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], and 4-amino-tertiary benzene is used instead of 2-methyl-5-aminopyridine. [Intermediate 2-a] (yield 76%) was obtained by the same method.

Synthesis of [Intermediate 2-b]

[Intermediate 2-b]

[Intermediate 2-b] (yield 47%) was obtained in the same manner using [Intermediate 2-a] synthesized in [Scheme 2-1] instead of [Intermediate 1-a] used in [Scheme 1-2]. Got it.

Scheme 2-3 Synthesis of [Intermediate 2-c]

[Intermediate 2-c]

2-chloropyridine-4-boronic acid (11.5 g, 0.073 mol), 1-bromonaphthalene (9.9 g, 0.061 mol), tetrakis (triphenylphosphine) palladium (3.62 g, 0.003 mol), potassium carbonate ( 16.9 g, 0.122 mol) was added to 150 mL of 1,4-dioxane, 150 mL of toluene, and 60 mL of distilled water, and refluxed for 12 hours. The mixture was cooled to room temperature, extracted with ethyl acetate, and separated by column chromatography, obtaining 11.4 g of Intermediate 2-c (yield 78%).

Synthesis of [Intermediate 2-d]

[Intermediate 2-d]

Instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], [Intermediate 2-c] synthesized in [Scheme 2-3] was used, and 3- instead of 2-methyl-5-aminopyridine. [Intermediate 2-d] (yield 72%) was obtained by the same method using fluorobenzeneamine.

Synthesis of [Intermediate 2-e]

[Intermediate 2-e]

Instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], 4-bromophenylboronic acid was used, and instead of 2-methyl-5-aminopyridine, [ [Intermediate 2-e] (yield 76%) was obtained in the same manner using Intermediate 2-d].

[Scheme 2-6] Synthesis of [Compound 2]

[Compound 2]

Instead of [Intermediate 1-d] used in [Scheme 1-5], [Intermediate 2-e] synthesized in [Scheme 2-5] was used, and instead of [Intermediate 1-b], [Scheme 2-2] [Compound 2] (yield 54%) was obtained by the same method using [Intermediate 2-b].

MS (MALDI-TOF): m / z 843.37 [M] ⁺

Synthesis Example 3. Synthesis of [Compound 3]

[Scheme 3-1] Synthesis of [Intermediate 3-a]

[Intermediate 3-a]

1-chloro-4-phenylbenzene was used instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], and 1-amino-3-methylbenzene was used instead of 2-methyl-5-aminopyridine. [Intermediate 3-a] (yield 73%) was obtained by the same method.

[Scheme 3-2] Synthesis of [Intermediate 3-b]

[Intermediate 3-b]

Instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], 4-bromo-1-naphthylboronic acid was used, and instead of 2-methyl-5-aminopyridine, [Scheme 3-1] [Intermediate 3-b] (yield 76%) was obtained by the same method using [Intermediate 3-a].

Synthesis of [Intermediate 3-c]

[Intermediate 3-c]

Instead of [Intermediate 1-d] used in [Scheme 1-5], [Intermediate 3-b] synthesized in [Scheme 3-2] was used, and 1,6-dibromopyrene instead of [Intermediate 1-b]. Was used to obtain [Intermediate 3-c] (yield 43%).

Synthesis of Intermediate 3-d

[Intermediate 3-d]

Phenylboronic acid was used instead of 2-chloropyridine-4-boronic acid used in [Scheme 2-3], and 2-amino-5-chloro-6-methylpyridine was used instead of 1-chloronaphthalene in the same manner [ Intermediate 3-d] (yield 72%).

[Scheme 3-5] Synthesis of [Intermediate 3-e]

[Intermediate 3-e]

(4-chlorophenyl) trimethylsilane was used instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], and synthesized in [Scheme 3-4] instead of 2-methyl-5-aminopyridine. [Intermediate 3-e] (yield 71%) was obtained by the same method using [Intermediate 3-d].

[Scheme 3-6] Synthesis of [Compound 3]

[Compound 3]

Instead of [Intermediate 1-d] used in [Scheme 1-5], [Intermediate 3-e] synthesized in [Scheme 3-5] was used, and instead of [Intermediate 1-b], [Scheme 3-3] [Compound 3] (yield 57%) was obtained by the same method using [Intermediate 3-c] synthesized in the above.

MS (MALDI-TOF): m / z 915.40 [M] ⁺

Synthesis Example 4. Synthesis of [Compound 4]

[Scheme 4-1] Synthesis of [Intermediate 4-a]

[Intermediate 4-a]

[Intermediate 4- in the same manner using 4-aminobenzeneboronic acid instead of 2-chloropyridine-4-boronic acid used in [Scheme 2-3], and pentadutereobromobenzene instead of 1-chloronaphthalene a] (yield 80%) was obtained.

[Scheme 4-2] Synthesis of [Intermediate 4-b]

[Intermediate 4-b]

Instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], 6-bromo-2,2'-bipyridine was used, and instead of 2-methyl-5-aminopyridine, [Scheme 4-1] [Intermediate 4-b] (yield 72%) was obtained by the same method using [Intermediate 4-a].

Synthesis of [Intermediate 4-c]

[Intermediate 4-c]

[Intermediate 4-c] (yield 42%) was obtained in the same manner using [Intermediate 4-b] synthesized in [Scheme 4-2] instead of [Intermediate 1-a] used in [Scheme 1-2]. Got it.

Scheme 4-4 Synthesis of Intermediate 4-d

[Intermediate 4-d]

In the same manner using 1-chloronaphthalene instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1] and 4-amino-tertiary benzene instead of 2-methyl-5-aminopyridine [Intermediate 4-d] (yield 74%) was obtained.

Synthesis of [Intermediate 4-e]

[Intermediate 4-e]

Instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], 4-bromophenylboronic acid was used, and instead of 2-methyl-5-aminopyridine, [ [Intermediate 4-e] (yield 77%) was obtained in the same manner using Intermediate 4-d].

[Scheme 4-6] Synthesis of [Compound 4]

[Compound 4]

Instead of [Intermediate 1-d] used in [Scheme 1-5], [Intermediate 4-e] synthesized in [Scheme 4-5] was used, and instead of [Intermediate 1-b], [Scheme 4-3] [Compound 4] (yield 57%) was obtained by the same method using [Intermediate 4-c].

MS (MALDI-TOF): m / z 877.42 [M] ⁺

Synthesis Example 5. Synthesis of [Compound 5]

Synthesis of [Intermediate 5-a]

[Intermediate 5-a]

2,5-Dibromonitrobenzene (250 g, 0.890 mol) and copper powder (135.74 g, 2.136 mol) were added to 1 L of dimethylformamide, and the temperature was raised to 125 ° C and stirred for 3 hours. The temperature was lowered to room temperature, and 500 mL of toluene was added and stirred. Recrystallization with methanol gave 139 g (yield 78%) of [Intermediate 5-a].

Synthesis of [Intermediate 5-b]

[Intermediate 5-b]

[Intermediate 5-a] (139.7 g, 0.347 mol) obtained in [Scheme 5-1] was added to 2 L of ethanol, and 1 L of 12 M hydrochloric acid was added thereto and stirred. Lowered to 0 ° C. and tin powder (165 g, 1.39 mol) was slowly added dropwise over 20 minutes. It was refluxed at 100 ° C. for 3 hours. After the reaction was completed, the temperature was lowered to 0 ° C., and 1 L of 12 M aqueous sodium hydroxide solution was slowly added to make a basic solution. Extraction with ethyl acetate and separation by column chromatography yielded 87.7 g (74% yield) of [Intermediate 5-b].

Synthesis of [Intermediate 5-c]

[Intermediate 5-c]

[Intermediate 5-b] (87.7 g, 0.256 mol) synthesized in [Scheme 5-2] was added to 380 mL of 12 M hydrochloric acid and 380 mL of distilled water. It was dissolved in 220 mL and slowly added dropwise and stirred for 1 hour. Potassium iodide was dissolved in 850 mL of distilled water and slowly added dropwise, and stirred at room temperature for 1 hour. The temperature was raised to 60 ° C. and stirred for 3 hours. Extraction with ethyl acetate and separation by column chromatography yielded 42.1 g (29% yield) of [Intermediate 5-c].

Synthesis of Intermediate 5-d

[Intermediate 5-d]

Intermediate 5-c synthesized in Reaction Scheme 5-3 (19.7 g, 35 mmol), tetrakis (triphenylphosphine) palladium (0.8 g, 0.5 mmol), and copper iodide (0.54 g, 1 mmol) To 50 mL of triethylamine and stirred at room temperature, phenylacetylene (3.6 mL, 35 mmol) was added slowly. After stirring for 1 hour at room temperature, 300 mL of hexane was added to terminate the reaction. Separation by column chromatography gave 13.2 g (yield 74%) of [Intermediate 5-d].

Synthesis of [Intermediate 5-e]

[Intermediate 5-e]

[Intermediate 5-d] (12.3 g, 0.024 mol) synthesized in the above [Scheme 5-4] was dissolved in 120 mL of dichloromethane. Iron trifluoromethanesulfonate (1.2 g, 0.002 mol) was added and refluxed for 12 hours. After hot filtering, the crystals were recrystallized to obtain 2.0 g (yield 16%) of [Intermediate 5-e].

Synthesis of Intermediate 5-f

[Intermediate 5-f]

1-chloro-3-phenylbenzene was used instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], and 4-amino-tertiary benzene was used instead of 2-methyl-5-aminopyridine. [Intermediate 5-f] (yield 74%) was obtained by the same method.

Synthesis of [Intermediate 5-g]

[Intermediate 5-g]

Instead of [Intermediate 1-a] used in [Scheme 1-2], [Intermediate 5-f] synthesized in [Scheme 5-6] was used, and [Scheme 5-5] instead of 1,6-dibromopyrene. [Intermediate 5-g] (yield 38%) was obtained by the same method using [Intermediate 5-e].

Synthesis of [Intermediate 5-h]

[Intermediate 5-h]

4-bromo-2-phenylpyridine is used instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], and 4-amino-tertiary benzene is used instead of 2-methyl-5-aminopyridine. Was used to obtain [Intermediate 5-h] (yield 73%).

Synthesis of [Intermediate 5-i]

[Intermediate 5-i]

4-bromo-2-phenylboronic acid is used instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], and in [Scheme 5-8] instead of 2-methyl-5-aminopyridine [Intermediate 5-i] (yield 75%) was obtained by the same method using the synthesized [Intermediate 5-h].

[Scheme 5-10] Synthesis of [Compound 5]

[Compound 5]

Instead of [Intermediate 1-d] used in [Scheme 1-5], [Intermediate 5-i] synthesized in [Scheme 5-9] was used, and instead of [Intermediate 1-b], [Scheme 5-7] [Compound 5] (yield 58%) was obtained by the same method using [Intermediate 5-g] synthesized in the above.

MS (MALDI-TOF): m / z 1029.50 [M] ⁺

Synthesis Example 6. Synthesis of [Compound 6]

Synthesis of [Intermediate 6-a]

[Intermediate 6-a]

In the same manner using (3-chlorophenyl) trimethylsilane instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1] and 1-naphthalenamine instead of 2-methyl-5-aminopyridine [Intermediate 6-a] (yield 76%) was obtained.

Synthesis of [Intermediate 6-b]

[Intermediate 6-b]

[Intermediate 6-b] (yield 44%) was obtained in the same manner using [Intermediate 6-a] synthesized in [Scheme 6-1] instead of [Intermediate 1-a] used in [Scheme 1-2]. Got it.

Synthesis of Intermediate 6-c

[Intermediate 6-c]

In the same manner using 3-chloro-6-methylpyridine instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1] and 4-aminoquinoline instead of 2-methyl-5-aminopyridine [Intermediate 6-c] (yield 75%) was obtained.

Synthesis of Intermediate 6-d

[Intermediate 6-d]

[Intermediate used in [Scheme 6-3] instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1] and 4-bromophenylboronic acid, and instead of 2-methyl-5-aminopyridine 6-c] was used to obtain [Intermediate 6-d] (yield 76%).

Scheme 6-5 Synthesis of Compound 6

[Compound 6]

Instead of [Intermediate 1-d] used in [Scheme 1-5], [Intermediate 6-d] synthesized in [Scheme 6-4] was used, and instead of [Intermediate 1-b], [Scheme 6-2] [Compound 6] (yield 57%) was obtained by the same method using [Intermediate 6-b].

MS (MALDI-TOF): m / z 800.30 [M] ⁺

Synthesis Example 7. Synthesis of [Compound 7]

Synthesis of [Intermediate 7-a]

[Intermediate 7-a]

2-bromo-5-trimethylsilylpyridine is used instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], and 1-amino-3-methylbenzene is used instead of 2-methyl-5-aminopyridine. [Intermediate 7-a] (yield 76%) was obtained by the same method using the method.

[Scheme 7-2] Synthesis of [Intermediate 7-b]

[Intermediate 7-b]

Instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], 4-bromo-1-naphthylboronic acid was used, and instead of 2-methyl-5-aminopyridine, [Scheme 7-1] [Intermediate 7-b] (yield 79%) was obtained by the same method using [Intermediate 7-a].

Scheme 7-3 Synthesis of Intermediate 7-c

[Intermediate 7-c]

Instead of [Intermediate 1-d] used in [Scheme 1-5], [Intermediate 7-b] synthesized in [Scheme 7-2] was used, and 1,6-dibromopyrene instead of [Intermediate 1-b]. [Intermediate 7-c] (yield 42%) was obtained in the same manner using.

Synthesis of Intermediate 7-d

[Intermediate 7-d]

In the same manner using (4-chlorophenyl) trimethylsilane instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1] and 4-aminoquinoline instead of 2-methyl-5-aminopyridine [Intermediate 7-d] (yield 74%) was obtained.

[Scheme 7-5] Synthesis of [Compound 7]

[Compound 7]

Instead of [Intermediate 1-a] used in [Scheme 1-2], [Intermediate 7-d] synthesized in [Scheme 7-4] was used, and instead of 1,6-dibromopyrene, the above [Scheme 7-3] [Compound 7] (yield 40%) was obtained by the same method using [Intermediate 7-c].

MS (MALDI-TOF): m / z 872.37 [M] ⁺

Synthesis Example 8. Synthesis of [Compound 8]

Synthesis of [Intermediate 8-a]

[Intermediate 8-a]

5-bromo-2,2'-bipyridine is used instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], and 2-pyridineamine is used instead of 2-methyl-5-aminopyridine. [Intermediate 8-a] (yield 76%) was obtained in the same manner.

Scheme 8-2 Synthesis of Intermediate 8-b

[Intermediate 8-b]

4-bromophenylboronic acid was used in place of 1-cyano-4-chlorobenzene used in [Scheme 1-1], and [Synthesis 8-1] was used instead of 2-methyl-5-aminopyridine. [Intermediate 8-b] (yield 78%) was obtained in the same manner using Intermediate 8-a].

Synthesis of Intermediate 8-c

[Intermediate 8-c]

Instead of [Intermediate 1-d] used in [Scheme 1-5], [Intermediate 8-b] synthesized in [Scheme 8-2] was used, and instead of [Intermediate 1-b], [Scheme 5-5] [Intermediate 8-c] (yield 43%) was obtained by the same method using [Intermediate 5-e].

Synthesis of Intermediate 8-d

[Intermediate 8-d]

4-bromodibenzofuran is used instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], and 1-amino-4-methylbenzene is used instead of 2-methyl-5-aminopyridine. [Intermediate 8-d] (yield 74%) was obtained by the method.

[Scheme 8-5] Synthesis of [Compound 8]

[Compound 8]

Instead of [Intermediate 1-a] used in [Scheme 1-2], [Intermediate 8-d] synthesized in [Scheme 8-4] was used, and [Scheme 8-3] instead of 1,6-dibromopyrene. Compound 8] (yield 42%) was obtained by the same method using [Intermediate 8-c].

MS (MALDI-TOF): m / z 947.36 [M] ⁺

Synthesis Example 9. Synthesis of [Compound 9]

Synthesis of Intermediate 9-a

[Intermediate 9-a]

Instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], 4-bromophenylboronic acid was used, and instead of 2-methyl-5-aminopyridine, [ [Intermediate 9-a] (yield 75%) was obtained in the same manner using Intermediate 1-a].

Scheme 9-2 Synthesis of [Intermediate 9-b]

[Intermediate 9-b]

Instead of [Intermediate 1-d] used in [Scheme 1-5], [Intermediate 9-b] synthesized in [Scheme 9-2] was used, and instead of [Intermediate 1-b], [Scheme 5-5] [Intermediate 9-b] (yield 44%) was obtained by the same method using [Intermediate 5-e].

[Scheme 9-3] Synthesis of Intermediate 9-c

[Intermediate 9-c]

[Intermediate 9-c] (yield 69%) was obtained by the same method using 5-bromo-1,10-phenanthroline instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1]. .

Scheme 9-4 Synthesis of Compound 9

[Compound 9]

Instead of [Intermediate 1-a] used in [Scheme 1-2], [Intermediate 9-c] synthesized in [Scheme 9-3] was used, and [Scheme 9-2] instead of 1,6-dibromopyrene. Compound 9] (yield 43%) was obtained by the same method using [Intermediate 9-b].

MS (MALDI-TOF): m / z 921.36 [M] ⁺

Synthesis Example 10 Synthesis of [Compound 10]

Synthesis of Intermediate 10-a

[Intermediate 10-a]

5-bromo-2,3-dimethylpyrazine was used instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], and 1-amino-3-methylbenzene was used instead of 2-methyl-5-aminopyridine. [Intermediate 10-a] (yield 76%) was obtained in the same manner using the same method.

Synthesis of [Intermediate 10-b]

[Intermediate 10-b]

[Intermediate 10-b] (yield 45%) was obtained in the same manner using [Intermediate 10-a] synthesized in [Scheme 10-1] instead of [Intermediate 1-a] used in [Scheme 1-2]. Got it.

Synthesis of [Intermediate 10-c]

[Intermediate 10-c]

The same method using 2-bromo-5-methylpyrazine instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1] and 1-naphthalenamine instead of 2-methyl-5-aminopyridine [Intermediate 10-c] (yield 75%) was obtained.

Synthesis of [Intermediate 10-d]

[Intermediate 10-d]

4-bromo-phenylboronic acid was used instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], and synthesized in [Scheme 10-3] instead of 2-methyl-5-aminopyridine. [Intermediate 10-d] (yield 73%) was obtained by the same method using [Intermediate 10-c].

Synthesis of [Compound 10]

[Compound 10]

Instead of [Intermediate 1-d] used in [Scheme 1-5], [Intermediate 10-d] synthesized in [Scheme 10-4] was used, and instead of [Intermediate 1-b], [Scheme 10-2] [Compound 10] (Yield 56%) was obtained by the same method using [Intermediate 10-b].

MS (MALDI-TOF): m / z 722.32 [M] ⁺

Synthesis Example 11. Synthesis of [Compound 11]

Synthesis of [Intermediate 11-a]

[Intermediate 11-a]

Instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], pentadutereoiodobenzene was used, and 3-amino-6-methylpyridazine was used instead of 2-methyl-5-aminopyridine. [Intermediate 11-a] (yield 77%) was obtained in the same manner.

Scheme 11-2 Synthesis of Intermediate 11-b

[Intermediate 11-b]

3-methylphenylboronic acid (17.4 g, 0.128 mol), 1,6-dibromopyrene (21.9 g, 0.061 mol), tetrakis (triphenylphosphine) palladium (3.62 g, 0.003 mol), potassium carbonate (25.3 g , 0.183 mol) was added to 75 mL of 1,4-dioxane, 75 mL of toluene, and 30 mL of distilled water, and refluxed for 12 hours. The mixture was cooled to room temperature, extracted with ethyl acetate, and separated by column chromatography to obtain 18.2 g (yield 78%) of [Intermediate 11-b].

Synthesis of [Intermediate 11-c]

[Intermediate 11-c]

[Intermediate 11-b] (19.1 g, 0.05 mol) obtained in [Scheme 11-2] was dissolved in 200 mL of dimethylformamide and stirred at 0 ° C. N-bromosuccinimide (20.1 g, 0.11 mol) was dissolved in 100 mL of dimethylformamide and slowly added dropwise for 1 hour. After raising to room temperature, the mixture was stirred for 12 hours. Filtered with excess distilled water, washed with methanol, and recrystallized with toluene and methanol to give 23.8 g (yield 88%) of [Intermediate 11-c].

Scheme 11-4 Synthesis of Intermediate 11-d

[Intermediate 11-d]

Instead of [Intermediate 1-a] used in [Scheme 1-2], [Intermediate 11-a] synthesized in [Scheme 11-1] was used, and [Scheme 11-3] instead of 1,6-dibromopyrene. [Intermediate 11-d] (yield 43%) was obtained by the same method using [Intermediate 11-c].

Synthesis of [Intermediate 11-e]

[Intermediate 11-e]

[Intermediate 11-e using the same method using 2-chloropyrimidine instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], and benzeneamine instead of 2-methyl-5-aminopyridine ] (Yield 78%).

Synthesis of Intermediate 11-f

[Intermediate 11-f]

4-bromo-1-naphthylboronic acid was used instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], and [Scheme 11-5] was used instead of 2-methyl-5-aminopyridine. [Intermediate 11-f] (yield 76%) was obtained by the same method using [Intermediate 11-e].

Scheme 11-7 Synthesis of Compound 11

[Compound 11]

Instead of [Intermediate 1-d] used in [Scheme 1-5], [Intermediate 11-f] synthesized in [Scheme 11-6] was used, and instead of [Intermediate 1-b], [Scheme 11-4] [Compound 11] (yield 53%) was obtained by the same method using [Intermediate 11-d].

MS (MALDI-TOF): m / z 865.39 [M] ⁺

Synthesis Example 12 Synthesis of [Compound 12]

Synthesis of Intermediate 12-a

[Intermediate 12-a]

4-bromo2-methylpyrimidine is used instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], and 1-naphthalenamine (D7) is used instead of 2-methyl-5-aminopyridine. [Intermediate 12-a] (yield 76%) was obtained by the same method.

Synthesis of Intermediate 12-b

[Intermediate 12-b]

[Intermediate 12-b] (yield 43%) was obtained by the same method using [Intermediate 12-a] synthesized in [Scheme 12-1] instead of [Intermediate 1-a] used in [Scheme 1-2]. Got it.

Synthesis of Intermediate 12-c

[Intermediate 12-c]

2-bromo-6-methylnaphthalene was used in place of 1-cyano-4-chlorobenzene used in [Scheme 1-1], and 2-tertiarytypyrimidine-4 instead of 2-methyl-5-aminopyridine [Intermediate 12-c] (yield 75%) was obtained by the same method using -amine.

Synthesis of Intermediate 12-d

[Intermediate 12-d]

Instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], 4-bromophenylboronic acid was used, and instead of 2-methyl-5-aminopyridine, [Synthesis 12-3] [Intermediate 12-d] (yield 77%) was obtained in the same manner using Intermediate 12-c].

Scheme 12-5 Synthesis of Compound 12

[Compound 12]

Instead of [Intermediate 1-d] used in [Scheme 1-5], [Intermediate 12-d] synthesized in [Scheme 12-4] was used, and instead of [Intermediate 1-b], [Scheme 12-2] [Compound 12] (yield 54%) was obtained by the same method using [Intermediate 12-b].

MS (MALDI-TOF): m / z 807.41 [M] ⁺

Synthesis Example 13. Synthesis of [Compound 13]

Synthesis of Intermediate 13-a

[Intermediate 13-a]

Diphenylamine (50 g, 0.295 mol) was added to 300 mL of dimethylformamide and stirred at 0 ° C. N-bromosuccinimide (107.8 g, 0.606 mol) was dissolved in 350 mL of dimethylformamide dropwise and stirred for 6 hours. Distilled water was filtered and washed with hexane. It was dissolved in dichloromethane and heated, and treated with acid clay and activated carbon. Washed with dichloromethane and recrystallized with hexane to give 80 g (yield 83%) of [Intermediate 13-a].

Synthesis of [Intermediate 13-b]

[Intermediate 13-b]

[Intermediate 13-a] (40 g, 0.122 mol), Bispinacolatodiborone (65.2 g, 0.257 mol) obtained in [Scheme 13-1], 1,1'-bis (diphenylphosphino) ferrocenedi Chloropalladium (3 g, 0.003 mol) and potassium acetate (48 g, 0.489 mol) were added to 652 mL of toluene and refluxed. Extraction with ethyl acetate and separation by column chromatography yielded 44 g (yield 85%) of [Intermediate 13-b].

Synthesis of Intermediate 13-c

[Intermediate 13-c]

[Intermediate 13-b] (44 g, 0.104 mol), 2-bromonitrobenzene (46,4 g, 0.23 mol) synthesized in the above Reaction Scheme 13-2, tetrakis (triphenylphosphine) palladium ( 3.62 g, 0.003 mol) and potassium carbonate (72.2 g, 0.522 mol) were added to 278.6 mL of 1,4-dioxane, 278.6 mL of toluene, and 92.8 mL of distilled water, and refluxed for 12 hours. The mixture was cooled to room temperature, extracted with ethyl acetate, and separated by column chromatography, obtaining 31.2 g of Intermediate 13-c (yield 61%).

Synthesis of [Intermediate 13-d]

[Intermediate 13-d]

[Intermediate 13-c] (10 g, 24.3 mmol), 1,6-dibromopyrene (7.3 g, 20.3 mmol), and 2,2'-bis (diphenylphosphino) synthesized in the above Reaction Scheme 13-3. ) -1-1'-binafphyl (0.25 g, 0.41 mmol), sodium tertiary review side (3.9 g, 40.6 mmol), tris (dibenzylideneacetone) dipalladium (0.37 g, 0.41 mmol) toluene 100 Put in mL and reflux for 24 h. Extraction with ethyl acetate and separation by column chromatography yielded 5.6 g (40% yield) of [Intermediate 13-d].

Synthesis of [Intermediate 13-e]

[Intermediate 13-e]

[Intermediate 13-d] (13.1 g, 0.019 mol) and triphenylphosphine (27 g, 0.095 mol) obtained in [Scheme 13-4] were added to 150 mL of 1,2-dichlorobenzene and refluxed for 10 hours. I was. Cooled to room temperature and separated by column chromatography to give 8 g (67% yield) of [Intermediate 13-e].

Synthesis of [Intermediate 13-f]

[Intermediate 13-f]

[Intermediate 13-e] (5 g, 0.008 mol) obtained in [Scheme 13-5], iodobenzene (8.1 g, 0.04 mol), copper powder (3.55 g, 0.056 mol), 18-crown-6 ( 0.8 g, 0.003 mol) and potassium carbonate (8.8 g, 0.064 mol) were added to 100 mL of 1,2-dichlorobenzene and refluxed at 180 ° C. for 2 days. Extraction with ethyl acetate was followed by column chromatography to obtain 4.9 g (79% yield) of [Intermediate 13-f].

Synthesis of [Intermediate 13-g]

[Intermediate 13-g]

The same method using 4-bromoquinoline instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1] and 6-methyl-3-pyridineamine instead of 2-methyl-5-aminopyridine [Intermediate 13-g] (yield 75%) was obtained.

Synthesis of [Intermediate 13-h]

[Intermediate 13-h]

4-bromophenylboronic acid was used instead of 1-cyano-4-chlorobenzene used in [Scheme 1-1], and [Synthesis 13-7] was used instead of 2-methyl-5-aminopyridine. [Intermediate 13-h] (yield 75%) was obtained in the same manner using Intermediate 13-g].

Scheme 13-9 Synthesis of Compound 13

[Compound 13]

Instead of [Intermediate 1-d] used in [Scheme 1-5], [Intermediate 13-h] synthesized in [Scheme 13-8] was used, and instead of [Intermediate 1-b], [Scheme 13-6] [Compound 13] (yield 52%) was obtained by the same method using [Intermediate 13-f].

MS (MALDI-TOF): m / z 1008.39 [M] ⁺

Examples 1 to 13 Preparation of Organic Light Emitting Diodes

The light emitting area of the ITO glass was patterned to have a size of 2 mm × 2 mm and then washed. After mounting the substrate in a vacuum chamber, the base pressure was 1 × 10 ^-6 torr, and the organic material was prepared on the ITO by DNTPD (700 kPa), α-NPD (300 kPa), BH1 as a host for the light emitting layer and prepared by the present invention. One of the compounds 1 to 13 (3 wt%) was co-deposited (300 kPa), and then deposited in the order of Alq ₃ (350 kPa), LiF (5 kPa), Al (1,000 kPa), and measured at 0.4 mA. .

[DNTPD] [α-NPD]

[BH1] [Alq ₃ ]

Comparative Examples 1 and 2

The organic light emitting device for Comparative Examples 1 to 2 was manufactured in the same manner except for using the following [Compound 101] and [Compound 102] instead of the compound prepared by the invention in the device structure of Examples 1 to 13 The structure is shown below.

[Compound 101] [Compound 102]

For the organic light emitting diodes manufactured according to Examples 1 to 13 and Comparative Examples 1 and 2, voltage, current density, luminance, color coordinates, and lifetime were measured and the results are shown in the following [Table 1]. T80 means the time it takes for the luminance to decrease to 80% from the initial luminance (5000nit).

division Host Dopant Voltage (V) Luminance (Cd / ㎡) CIEx CIEy T ₈₀ Example 1 BH1 Compound 1 3.8 711 0.136 0.098 59 Example 2 BH1 Compound 2 3.8 732 0.137 0.100 63 Example 3 BH1 Compound 3 3.8 708 0.137 0.099 60 Example 4 BH1 Compound 4 3.8 697 0.138 0.099 60 Example 5 BH1 Compound 5 3.9 729 0.137 0.098 63 Example 6 BH1 Compound 6 3.8 709 0.136 0.100 61 Example 7 BH1 Compound 7 3.7 722 0.137 0.102 60 Example 8 BH1 Compound 8 3.8 706 0.137 0.103 59 Example 9 BH1 Compound 9 3.8 734 0.139 0.100 60 Example 10 BH1 Compound 10 3.9 711 0.137 0.099 63 Example 11 BH1 Compound 11 3.9 713 0.139 0.101 60 Example 12 BH1 Compound 12 3.7 709 0.138 0.098 62 Example 13 BH1 Compound 13 3.8 699 0.138 0.099 61 Comparative Example 1 BH1 Compound 101 6.4 515 0.149 0.166 46 Comparative Example 2 BH1 Compound 102 6.0 653 0.175 0.225 57

As shown in [Table 1], the pyrene derivative having an asymmetric structure according to the present invention has significantly improved color purity of blue and excellent light emission characteristics such as luminance compared to the case of using a conventional pyrene-based arylamine compound in an organic light emitting device. As can be seen, accordingly, the organic electroluminescent device including the pyrene derivative according to the present invention as an organic light emitting compound has a high applicability as an organic light emitting device for implementing full color.

Claims (19)

A pyrene derivative represented by the following [Formula A] or [Formula B] and having an asymmetric structure:
[Formula A] [Formula B]

In [Formula A] and [Formula B],
Py is a substituted or unsubstituted pyridinyl group or a substituted or unsubstituted 6-membered aromatic heteroaryl group, two of the six-membered ring is a nitrogen atom and the rest are carbon atoms,
Ar ₁ to Ar ₃ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 5 to 50 carbon atoms and at least one selected from O, N, S, P and Si as a substituted or unsubstituted hetero atom It is selected from a heteroaryl group having 2 to 50 carbon atoms,
L is selected from a substituted or unsubstituted aryl group having 5 to 50 carbon atoms and a heteroaryl group having 2 to 50 carbon atoms having any one or more selected from O, N, S, P, and Si as a substituted or unsubstituted hetero atom; ,
n is an integer of 1 to 3, when n is 2 or more, a plurality of L may be the same or different from each other,
Z is selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted hetero atom and selected from O, N, S, P and Si It is selected from a heteroaryl group having 2 to 50 carbon atoms having at least one,
m is an integer of 1 to 8, and when m is 2 or more, a plurality of Zs are the same or different from each other,
Among the carbon atoms in the pyrene ring of [Formula A] or [Formula B], those which do not bond with the nitrogen atom or the plurality of Z of the amine are bonded with hydrogen,
In the pyrene derivative represented by the above [Formula A] to [Formula B], the amine is bonded to position 1, 6 or 2, 7, respectively,
At least one of Py and Ar ₁ to Ar ₃ is a deuterium, 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, or a hetero having 3 to 18 carbon atoms. Substituted with one or more substituents selected from an aryl group, an alkylsilyl group having 1 to 12 carbon atoms, and an arylsilyl group having 6 to 18 carbon atoms,
Py and Ar ₁ are not identical to each other, and Ar ₂ and Ar ₃ are not identical to each other. delete delete The method of claim 1,
At least one selected from Ar ₁ to Ar ₃ bonded to the amines of [Formula A] to [Formula B] includes deuterium, or pyrene derivative characterized in that the Py comprises deuterium. delete delete delete delete delete delete delete delete delete delete A first electrode; A second electrode opposed to the first electrode; And an organic layer interposed between the first electrode and the second electrode.
An organic light emitting device, characterized in that the organic layer comprises at least one pyrene derivative according to claim 1. The method of claim 15,
And the organic layer comprises at least one of a hole injection layer, a hole transport layer, a hole injection function, and a hole injection function, and a functional layer, a light emitting layer, an electron transport layer, and an electron injection layer. The method of claim 15,
The organic layer interposed between the first electrode and the second electrode includes a light emitting layer, the light emitting layer is composed of a host and a dopant, wherein the pyrene derivative is used as a dopant. The method of claim 16,
Wherein each of the layers is formed by a deposition process or a solution process, respectively. The method of claim 15,
The organic light emitting device is an organic light emitting device, characterized in that used in the device selected from a flat panel display device, a flexible display device, a flat or white flat illumination device and a single or white flexible lighting device.

Images