KR20150009297A - An organoelectroluminescent compounds and organoelectroluminescent device using the same - Google Patents

Abstract

The present invention relates to an organic electroluminescent compound represented by chemical formula 1, and to an organic electroluminescent device including the same. According to the present invention, the electroluminescent device has excellent brightness and light emitting efficiency. At the same time, the electroluminescent device can be operated with low voltages and thus has enhanced electric power efficiency.

Description

[0001] The present invention relates to an organic electroluminescent compound and an organic electroluminescent device using the same,

The present invention relates to an organic light emitting compound and an organic electroluminescent device including the same.

In recent years, organic light emitting devices capable of being driven by a low voltage in a self-emission type are superior in viewing angle and contrast ratio compared to a liquid crystal display, which is a mainstream of a flat panel display device, require no backlight and are lightweight and thin, And has been attracting attention as a next generation display device.

An organic electroluminescent device is a device that injects electric charge into an organic light emitting layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode) to form an electron and a hole.

The organic electroluminescent device can be formed on a transparent substrate that can be made of plastic and can be driven at a voltage as low as 10 V or less as compared with a plasma display panel or an inorganic electroluminescent display and has a relatively low power consumption , And has an advantage of excellent color. In addition, organic electroluminescent devices are capable of displaying three colors of green, blue, and red, and thus are attracting much attention as next-generation rich color display devices.

The most important factor determining the luminous efficiency in an organic electroluminescent device is a light emitting material. However, the development of a phosphorescent material on a light-emitting mechanism is one of the ways that the luminous efficiency can be improved more theoretically. Accordingly, a variety of phosphorescent materials have been developed to date, Particularly, CBP (4,4'-N, N'-dicarbazolbiphenyl) is the most widely known phosphorescent host material, and materials in which various substituents are introduced into carbazole are disclosed in Japanese Patent Laid-Open Publication No. 2008-214244 2003-133075) or an organic electroluminescent device using a BALq derivative as a host.

However, an organic electroluminescent device using a phosphorescent material has a significantly higher current efficiency than a device using a fluorescent material. However, when a material such as BAlq or CBP is used as a host of a phosphorescent material, There is no great advantage in terms of power efficiency due to a high voltage and a satisfactory level in terms of lifetime of a device can not be attained. Therefore, development of a high-performance host material with a more stable driving voltage and lifetime characteristics is required.

An object of the present invention is to provide an organic electroluminescent compound having an improved brightness and luminous efficiency, and at the same time lower voltage driving than conventional materials.

Further, the present invention is intended to provide an organic electroluminescent device that can be driven at a low voltage by employing the organic electroluminescent compound as a light emitting material, thereby further improving power efficiency, brightness, and efficiency.

In order to solve the above problems, the present invention provides an organic luminescent compound represented by the following formula (1).

[Chemical Formula 1]

In the above formula (1), A is selected from the following formulas (I) to (III).

[Chemical Formula I] [Chemical Formula II] [Chemical Formula III]

Further, the present invention is a liquid crystal display device comprising a first electrode, a second electrode facing the first electrode, and at least one organic layer interposed between the first electrode and the second electrode, The organic electroluminescent device includes at least one organic electroluminescent compound to be displayed.

Specific substituents of the organic luminescent compound represented by the formula (1) according to the present invention will be described later.

When the organic electroluminescent compound according to the present invention is employed in an organic electroluminescent device, it is possible to realize a device having low power driving efficiency, high power efficiency and high efficiency.

1 is a conceptual view illustrating a structure of an organic electroluminescent device according to an embodiment of the present invention.

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

The organic luminescent compound according to the present invention is characterized by being a compound represented by the following formula (1).

[Chemical Formula 1]

In the above formula (1), A is selected from the following formulas (I) to (III).

[Chemical Formula I] [Chemical Formula II] [Chemical Formula III]

X ₁ to X ₈ are the same as or different from each other and each independently N or CR ₁₂ .

R ₁ to R ₁₂ are the same or different from each other and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C2-C50 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2- A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxyl group having 5 to 50 carbon atoms, A substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms. A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 5 to 50 carbon atoms.

L represents a single bond or a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon group having 2 to 30 carbon atoms A substituted or unsubstituted C2-C30 alkynylene group, a substituted or unsubstituted C3-C30 A substituted or unsubstituted arylene group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, n is an integer of 0 to 3, and n is 2 or more The plural Ls may be the same or different from each other.

R ₁ to R ₁₂ and L may be bonded to each other or adjacent substituents to form a single alicyclic or aromatic ring or polycyclic ring, and the carbon atom of the ring formed may be selected from N, S, O, and P And may be substituted with any one or more hetero atoms.

'*' In the above formulas (I) to (III) means a site bound to the above formula (I).

The 'substituted' in the 'substituted or unsubstituted' may be a substituent selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl having 1 to 20 carbon atoms, alkenyl having 1 to 20 carbon atoms, alkynyl having 1 to 20 carbon atoms, A halogenated alkyl group having 1 to 20 carbon atoms, an aryl group having 5 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 5 to 24 carbon atoms, , An arylsilyl group having 5 to 24 carbon atoms, an alkylamine group having 1 to 20 carbon atoms, and an arylamine group having 6 to 24 carbon atoms, wherein R ₁ to R ₁₂ and L Lt; / RTI > may each be independently further substituted by such substituents.

The carbon number range of the alkyl group or aryl group in the 'substituted or unsubstituted alkyl group having 1 to 30 carbon atoms' or the 'substituted or unsubstituted aryl group having 5 to 50 carbon atoms' Quot; means the total number of carbon atoms constituting the alkyl moiety or the aryl moiety when it is regarded as unsubstituted. For example, a phenyl group substituted with a butyl group at the para position means an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

According to one embodiment of the present invention, L may be a single bond or any one of the linking groups selected from the following Structural Formulas A1 to A16.

[Structural formula A1] [Structural formula A2] [Structural formula A3] [Structural formula A4]

[Structural formula A5] [Structural formula A6] [Structural formula A7] [Structural formula A8]

[Structural formula A9] [Structural formula A10] [Structural formula A11] [Structural formula A12]

[Structural formula A13] [Structural formula A14] [Structural formula A15] [Structural formula A16]

In the above structural formulas A1 to A16, hydrogen or deuterium may be bonded to the carbon of the aromatic ring in each structural formula.

Meanwhile, the aryl group contained in the organic luminescent compound according to the present invention includes an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and includes a single or fused ring system containing 5 to 7 atoms, preferably 5 or 6 atoms And when a substituent is present in the aryl group, it may be fused with an adjacent substituent to further form a ring.

On the other hand, the aryl group which is a substituent used in the present invention is an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and includes a single or fused ring system containing 5 to 7 atoms, preferably 5 or 6 atoms, When a substituent is present in the aryl group, the adjacent substituent may be fused with each other to form a ring.

Specific examples of the aryl group include a phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, o-biphenyl group, m-biphenyl group, Naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group, anthryl group, phenanthryl group, naphthyl group, An aromatic group such as a fluorenyl group, a pyrenyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a pyrenyl group, a perylene group, a crycenyl group, a naphthacenyl group and a fluoranthenyl group.

At least one hydrogen atom of the aryl group may be replaced by a substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH (R) 'And R''each independently represent an alkyl group having 1 to 10 carbon atoms, which is referred to as an "alkylamino group" in this case), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, 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 present invention may be any one selected from the following Structural Formulas 1 to 6:

[Structural formula 1] [Structural formula 2] [Structural formula 3]

[Structural formula 4] [Structural formula 5] [Structural formula 6]

In the above Structural Formulas 1 to 6,

T ₁ to T ₈ may be the same or different and each independently selected from C (R ₄₁ ), C (R ₄₂ ) (R ₄₃ ), N, N (R ₄₄ ) , R ₃₁ to R ₄₄ are the same or different from each other and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, An aryl group having 5 to 30 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms having a substituted or unsubstituted heteroatom, O, N, S, or P, and each of [structural formulas 1] to [ In the structural formula 6, R ₃₁ to R ₄₄ May form a single bond with a substituent in the above-mentioned formula (1) or (I) to (III).

The above-mentioned [formula 3] may include a compound represented by the following formula [3] by a resonance structure according to the movement of electrons.

[Structural Formula 3-1]

In the above structural formula 3-1, T ₁ to T ₅ and R ₃₃ and R ₃₄ are the same as defined above.

Further, according to a preferred embodiment of the present invention, the above Structural Formulas 1 to 6 can be selected from the following Structural Formula 7.

[Structural Formula 7]

In the above formula 7,

X is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 30 carbon atoms, an unsubstituted or substituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms An amino group, a substituted or unsubstituted aryl group having 5 or more carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms having O, N, S or P as a hetero atom, a cyano group, a nitro group, M is an integer of 1 to 11, and when m is 2 or more, a plurality of X's are the same or different from each other, and any one of the at least one X is selected from the group consisting of the formula (1) ] To [Formula III].

Specific examples of the alkyl group as the substituent used in the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, , An octyl group, a stearyl group, a trichloromethyl group, and a trifluoromethyl group, and at least one hydrogen atom of the alkyl group may be substituted with a substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a trifluoromethyl group, (in this case, "alkylsilyl group" hereinafter), a substituted or unsubstituted amino group (-NH _2, -NH (R), -N (R ') (R "), where R, R' and R" are each A hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, an alkyl group having 1 to 24 carbon atoms (preferably an alkyl group having 1 to 24 carbon atoms) A halogenated alkyl group, an alkenyl group having 2 to 24 carbon atoms, an alkoxy group having 2 to 24 carbon atoms A heteroaryl group having 1 to 24 carbon atoms, an aryl group having 5 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 3 to 24 carbon atoms, or a heteroarylalkyl group having 3 to 24 carbon atoms.

Specific examples of the alkoxy group used in the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, And may be substituted with the same substituents as those in the case of the alkyl group.

Specific examples of the halogen group which is a substituent used in the compound of the present invention include fluorine (F), chlorine (Cl), bromine (Br) and the like.

The aryloxy group which is a substituent used in the present invention means an -O-aryl radical, wherein the aryl group is as defined above, and specific examples thereof include phenoxy, naphthoxy, anthracenyloxy, phenanthrenyloxy, fluorenyl Oxy, indenyloxy and the like, and at least one hydrogen atom contained in the aryloxy group may be further substituted.

Specific examples of the silyl group used in the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl, methylcyclobutylsilyl , Dimethyl furyl silyl and the like.

Specific examples of the alkenyl group used in the present invention include straight chain or branched chain alkenyl groups and include 3-pentenyl, 4-hexenyl, 5-heptenyl, 4-methyl- Dimethyl-pentenyl group, 6-methyl-5-heptenyl group and 2,6-dimethyl-5-heptenyl group.

The organic luminescent compound represented by the formula (1) according to the present invention may be more specifically selected from the following compounds [compounds 1] to [88].

[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]

The present invention also provides a method of manufacturing a thin film transistor comprising a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode, May be contained in one or more of the organic electroluminescent compounds.

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 light emitting layer may be composed of a host and a dopant, and the organic light emitting compound of the present invention may be used as a host.

In the present invention, a dopant material may be used for the light emitting layer in addition to the host. When the light emitting layer includes a host and a dopant, the dopant content may be selected generally in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host.

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

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

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

First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

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

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- ] Can be used.

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 (naphthalene-1-yl) -N, N'-diphenylbenzidine (? -NPD).

A hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method to form a thin film on the organic light emitting layer 50 can do. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level . In this case, the hole blocking material to be used is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having an electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

Wherein as material used for the hole blocking layer, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq _2, OXD-7, Liq and [Formula 101] to [Chemical Formula 107] either, but one that can be used is selected from, this limited It is not.

BAlq BCP Bphen

TPBI NTAZ BeBq ₂

OXD-7 Liq

(101)

≪ RTI ID = 0.0 >

Formula 107

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.

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- olate: Bebq2), ADN, [Compound 201], [Compound 202], oxadiazole derivative PBD, BMD, BND and the like may be used.

TAZ BAlq

[Compound 201] [Compound 202] BCP

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

≪ 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.

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

OA is a monovalent ligand capable of single bond or coordination bond with M, O is oxygen, 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, 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, and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having a hetero atom O, N, or S.

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

The Y may be the same or different and independently selected from the following formulas [C1] to [C39].

[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.

L represents 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 group having 5 to 30 carbon atoms 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, an aryl group having 3 to 20 carbon atoms, A heteroaryl group, a cyano group, a halogen group, deuterium, and hydrogen, and may be connected to an adjacent substituent by an alkylene or an alkenylene to form a spiro ring or a fused ring.

The organic electroluminescent device according to the present invention is characterized in that the organic layer comprises a light emitting layer and the light emitting layer further comprises at least one phosphorescent dopant in addition to at least one organic light emitting compound represented by the general formula (1) The luminescent dopant to be applied to the organic electroluminescent device is not particularly limited, but may be at least one compound selected from compounds represented by the following general formulas A-1 to J-1.

[General Formula A-1]

ML ₁ L ₂ L ₃

Wherein M is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, preferably Ir, Pt, Pd, Rh, Re , Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag. L ₁ , L ₂ and L ₃ are the same or different from each other as ligands, and each independently selected from the following structural formula [D], but are not limited thereto.

* In the following [structural formula D] represents a site coordinated to the metal ion M.

[Structural formula D]

In the above structural formula D,

A substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1- A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 heteroaryl 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 the like.

Each R is independently selected from the group consisting of 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, a heteroaryl group having 3 to 20 carbon atoms, a cyano group, a halogen group, deuterium and hydrogen And may be further substituted with one or more substituents.

The R may be connected to each adjacent substituent by alkylene or alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring.

The L may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring.

As one example, the dopant represented by the above-mentioned [formula A-1] may be any one selected from the following compounds.

[Formula B-1]

In the above general formula B-1,

M ^A1 represents the same metal ion as defined in [formula A-1], and Y ^A11 , Y ^A14 , Y ^A15 and Y ^A18 Each independently represent a carbon atom or a nitrogen atom, Y ^A12, Y ^A13, Y ^A16 and Y ^A17 each independently represents a substituted or unsubstituted carbon atoms, a substituted or unsubstituted nitrogen atom, an oxygen atom, a sulfur atom, the L ^A11 , L ^A12 , L ^A13 and L ^A14 each represent a linking group as defined above, and Q ^A11 and Q ^A12 represent a partial structure containing an atom bonding to M ^A1 .

Exemplary structures of the compound represented by the above-mentioned general formula B-1 are shown below, but the present invention is not limited thereto.

[Formula C-1]

In the above general formula (C-1)

M ^B1 represents the same metal ion as defined from the following formula ^{A-1], Y B11,} Y B14, Y B15 and Y ^B18 each independently represents a carbon atom or a nitrogen ^{atom, Y B12, Y B13, Y} B16 And Y ^B17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom, a sulfur atom, L ^B11 , L ^B12 , L ^B13 and L ^B14 represent a linking group, Q ^B11 and Q ^B12 represents a partial structure containing an atom bonding to M ^B1 .

Exemplary structures of the compound represented by the above-mentioned general formula C-1 are shown below, but the present invention is not limited thereto.

[Formula D-1]

In the above general formula (D-1)

M ^C1 represents a metal ion as defined in [formula A-1], R ^C11 and R ^C12 each independently represent a hydrogen atom, a substituent which is connected to each other to form a 5-membered ring, Each of R ^C13 and R ^C14 independently represents a hydrogen atom, a substituent which is connected to each other to form a 5-membered ring, or a substituent which does not have any one to be connected to each other, and G ^C11 and G ^C12 each independently represent a nitrogen atom, a substituent Or an unsubstituted carbon atom, L ^C11 and L ^C12 represent a linking group, and Q ^C11 and Q ^C12 represent a partial structure containing an atom bonding to M ^C1 .

Exemplary structures of the compound represented by the above-mentioned general formula (D-1) are shown below, but the present invention is not limited thereto.

[Formula E-1]

In the above general formula E-1,

M ^D1 represents a metal ion as defined in [Formula A-1], G ^D11 and G ^D12 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, and J ^D11 , J ^D12 , J ^D13 , J ^D14 each independently represents an atomic group necessary for forming a five-membered ring, and L ^D11 and L ^D12 represent a linking group.

Exemplary structures of the compound represented by the above-mentioned [formula E-1] are shown below, but the present invention is not limited thereto.

[Formula F-1]

In the above general formula F-1,

M ^E1 represents the same metal ion as defined in [Formula A-1], J ^E11 and J ^E12 each independently represent an atom group necessary for forming a 5-membered ring, and G ^E11 , G ^E12 , G ^E13 and G ^E14 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, and Y ^E11 , Y ^E12 , Y ^E13 and Y ^E14 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom.

Exemplary structures of the compound represented by the above-mentioned general formula F-1 are shown below, but the present invention is not limited thereto.

[Formula G-1]

In the above general formula G-1,

M ^F1 represents the same metal ion as defined in [formula A-1].

L ^F11 , L ^F12 and L ^F13 represent a linking group, R ^F11 , R ^F12 , R ^F13 and R ^F14 represent substituents, R ^F11 and R ^F12 , R ^F12 And R ^F13 , R ^F13 and R ^F14 may be connected to form a ring, wherein the ring formed by R ^F1 and R ^F12 , R ^F13 and R ^F14 is a 5-membered ring. And Q ^F11 and Q ^F12 represent a partial structure containing an atom bonding to M ^F1 .

Exemplary structures of the compound represented by the above-mentioned general formula G-1 are shown below, but the present invention is not limited thereto.

[Formula H-1] [Formula H-2] [Formula H-3]

In the above general formula H-1,

R ¹¹ and R ¹² are substituents of alkyl, aryl or heteroaryl; And q11 and q12 may be an integer of 0 to 4, preferably 0 to 2, and may form a fused ring with substituents adjacent to each other.

When q11 and q12 are 2 to 4, a plurality of R11 and R12 may be the same or different.

L ¹ is a ligand which binds to platinum and is preferably a ligand capable of forming an ortho metal platinum complex, a nitrogen-containing heterocyclic ligand, a diketone ligand, or a halogen ligand, more preferably an ortho metal ) Ligand forming a platinum complex, a bipyridyl ligand, or a phenanthroline ligand.

n ¹ is an integer of 0 to 3, preferably 0, m ¹ is 1 or 2, and preferably 2.

It is preferable that n ¹ and m ¹ denote the metal complex represented by the general formula H-1 as a neutral complex.

R ²¹ , R ²² , n ² , m ² , q ²² and L ² are the same as R ¹¹ , R ¹² , n ¹ , m ¹ , q ¹² and L ¹ in the general formula H-2, q ²¹ is an integer of 0 to 2, preferably 0.

Wherein R ³¹ , n ³ , m ³ and L ³ are the same as R ¹¹ , n ¹ , m ¹ and L ¹ , q ³¹ is an integer of 0 to 8, 2 is preferable, and 0 is more preferable.

Examples of the specific compounds of the above-mentioned general formulas H-1 to H-3 are as follows, but are not limited thereto.

[Formula I-1]

In the above general formula I-1,

Ring A, ring B, ring C and ring D represents a nitrogen-containing heterocyclic ring which may have a substituent, and the remaining two rings are an aryl ring which may have a substituent And may form a condensed ring with ring A and ring B, ring A and ring C and / or ring B and ring D, respectively. X ¹ , X ² , X ³ and X ⁴ represent a nitrogen atom in which two of them coordinate to a platinum atom, and the remaining two represent a carbon atom or a nitrogen atom. Q ¹ , Q ² and Q ³ each independently represent a divalent atom (or a bond), but Q ¹ , Q ² and Q ³ do not simultaneously represent a bond. ^{Two of} Z ¹ , Z ² , Z ³ and Z ⁴ represent coordinate bond, and the remaining two represent a covalent bond, an oxygen atom or a sulfur atom.

Examples of the specific compounds of the above-mentioned general formula I-1 include, but are not limited to, the following.

[Formula J-1]

In the above general formula J-1,

M represents the same metal ion as defined in [formula A-1], Ar1 represents a substituted or unsubstituted cyclic structure, and two azomethine bonds (-C = N-) , The nitrogen atom (N) binds to the M, respectively, and forms a three-coordinate ligand which is bonded to the M at the 3-position as a whole.

Further, in Ar 1, C represents a carbon atom constituting a ring structure represented by Ar 1. R 1 and R 2 may be the same or different and each represents a substituted or unsubstituted alkyl group or aryl group, and L represents a one-dimensional ligand.

In the above general formula J-1, it is preferable that M is Pt. The above-mentioned Ar1 is preferably selected from a 5-membered ring, a 6-membered ring and condensed ring group thereof.

Examples of the specific compounds of the above-mentioned general formula J-1 include, but are not limited to, the following.

In addition, the light emitting layer may further include various dopants and various hosts in addition to the dopant and the host.

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, Means a method of forming a thin film by evaporating a material used as a material for forming each of the layers by heating or the like under a vacuum or a low pressure state and the solution process is used as a material for forming each of the layers Means a method of forming a thin film by a method such as ink jet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating and the like.

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

[ Synthetic example  1] Synthesis of Compound 1

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

[Intermediate 1-a]

1-Nitronaphthalene (97 g, 0.56 mol), methyl cyanoacetate (166.5 g, 1.68 mol), potassium cyanide (40.1 g, 0.62 mol) and potassium hydroxide (62.9 g, 1.12 mol) were added and stirred. Then 970 mL of dimethylformamide was added and the mixture was stirred at 60 ° C overnight. The solvent was removed by concentrating under reduced pressure at room temperature, 500 mL of a 10% sodium hydroxide aqueous solution was added, and the mixture was refluxed for about 1 hour. The reaction mixture was extracted with ethyl acetate and then separated by column chromatography. The residue was recrystallized from toluene and heptane to obtain 50.8 g of [intermediate 1-a] (yield: 54%).

[Synthesis of Reaction Scheme 1-2] [Intermediate 1-b]

[Intermediate 1-b]

[Intermediate 1-a] (25.0 g, 149 mmol) obtained in the above Reaction Scheme 1-1 was placed in 200 mL of tetrahydrofuran and stirred. Added dropwise phenyl magnesium bromide _{(3.0 M in Et 2 O)} (87.4 mL, 297 mmol) and was refluxed for about 1 hour at 0 ℃. Ethyl chloroformate (19.4 g, 179 mmol) was added dropwise and refluxed for about 1 hour. The aqueous ammonium chloride solution was added until it became slightly acidic, and washed with water and heptane to obtain 32.4 g (yield 80%) of [intermediate 1-b].

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

[Intermediate 1-c]

[Intermediate 1-b] (30 g, 110 mmol) obtained in the above Reaction Scheme 1-2 was placed in about 80 mL of phosphorus oxychloride and refluxed overnight. After cooling to -20 ° C, approximately 400 mL of distilled water was slowly added. Washed with distilled water, methanol and heptane, and recrystallized from toluene and heptane to obtain 14.1 g of [intermediate 1-c] (yield: 44%).

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

[Intermediate 1-d]

1-Bromo-2-methylnaphthalene (10 g, 45.2 mmol) was added to 50 mL of sulfuric acid and stirred. After cooling to 0 ° C, nitric acid (2.9 mL, 67.8 mmol) was slowly added dropwise and stirred for about 2 hours. The reaction mixture was neutralized, extracted with ethyl acetate, and then subjected to column chromatography to obtain 3.5 g (yield: 29%) of Intermediate 1-d.

[Reaction Scheme 1-5] Synthesis of [Intermediate 1-e]

[Intermediate 1-e]

(3.5 g, 13.1 mmol), en-bromosuccinimide (2.3 g, 13.1 mmol) and dibenzoyl peroxide (0.32 g, 1.31 mmol) obtained in the above Reaction Scheme 1-4 Was added to 100 mL of carbon tetrachloride and stirred for about 3 hours. The reaction mixture was extracted with ethyl acetate and then separated by column chromatography to obtain 2.9 g (yield 65%) of Intermediate 1-e.

[Reaction Scheme 1-6] Synthesis of [Intermediate 1-f]

[Intermediate 1-f]

50 mL of toluene was added to [Intermediate 1-e] (2.8 g, 8.2 mmol) and triphenylphosphine (2.6 g, 9.9 mmol) obtained in the above Reaction Scheme 1-5 and refluxed at 120 ° C for about 12 hours. And washed with methanol to obtain 4.8 g (yield 97%) of Intermediate 1-f.

Synthesis of [Reaction Scheme 1-7] [Intermediate 1-g]

[Intermediate 1-g]

[Intermediate 1-f] (4.6 g, 7.6 mmol) and sodium bis (trimethylsilyl) amide (2.8 g, 15.2 mmol) obtained in the above Reaction Scheme 1-6 were added to 50 mL of tetrahydrofuran and stirred. After cooling to -78 ° C, 2-bromo-3-nitrobenzaldehyde (1.9 g, 8.4 mmol) was slowly added dropwise and stirred for about 12 hours. The temperature was raised to room temperature, stirred for about 72 hours, extracted with ethyl acetate, and then separated by column chromatography to obtain 2.7 g (yield 75%) of Intermediate 1-g.

[Reaction Scheme 1-8] Synthesis of [Intermediate 1-h]

[Intermediate 1-h]

[Intermediate 1-g] (2.7 g, 5.8 mmol) and copper powder (0.4 g, 5.8 mmol) obtained in the above Reaction Scheme 1-7 were dissolved in 30 mL of dimethylformamide and refluxed at 120 ° C. for about 12 hours . Extracted with ethyl acetate, and then separated by column chromatography to obtain 1.5 g of [intermediate 1-h] (yield: 85%).

[Reaction Scheme 1-9] Synthesis of [Intermediate 1-i]

[Intermediate 1-i]

(9: 1, v / v) of intermediate [1-h] (1.5 g, 4.9 mmol), iron (0.8 g, 14.8 mmol) and hydrochloric acid (8.7 mL) obtained in the above Reaction Scheme 1-8 were dissolved in methanol / distilled water And stirred at room temperature for 12 hours. After extraction with ethyl acetate, the product was separated by column chromatography to obtain 0.9 g of [intermediate 1-i] (yield 80%).

[Reaction Scheme 1-10] Synthesis of [Compound 1]

[Compound 1]

60% Sodium hydride (1.4 g, 20.5 mmol) and 20 mL of dimethylformamide were added thereto, followed by stirring for about 30 minutes. [Intermediate 1-i] (4.1 g, 17.1 mmol) obtained in [Scheme 1-9] and 50 mL of dimethylformamide were added dropwise thereto, followed by stirring for about 1 hour. [Intermediate 1-c] (6 g, 20.6 mmol) obtained in the above Scheme 1-3 and 50 mL of dimethylformamide were added and stirred overnight. 300 mL of distilled water was added, and the resulting solid was filtered. And recrystallized from toluene to obtain 5.9 g (yield 70%) of [Compound 1].

MS (MALDI-TOF): m / z 495.17 [M ^< ⁺ &^gt;].

[ Synthetic example  2] Synthesis of Compound 2

Synthesis of [Reaction Scheme 2-1] [Intermediate 2-a]

[Intermediate 2-a]

Synthesis was carried out in the same manner as in [Scheme 1-1] to [Scheme 1-3] except that heptadioneonononaphthalene was used instead of 1-nitronaphthalene used in the above Reaction Scheme 1-1 to obtain [Intermediate 2-a ] (Yield: 42%).

[Synthesis 2-2] Synthesis of [Compound 2]

[Compound 2]

Compound [2] (yield: 70%) was synthesized in the same manner as Intermediate 1-c except for using [Intermediate 2-a] obtained in the above Reaction Scheme 2-1 instead of [Intermediate 1-c] .

MS (MALDI-TOF): m / z 501.21 [M ^< ⁺ &^gt;].

[ Synthetic example  3] Synthesis of Compound 13

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

[Intermediate 3-a]

Was synthesized in the same manner as in [Scheme 1-1] to [Scheme 1-3] except that pyridine-4-ylmagnesium bromide was used in place of the phenylmagnesium bromide used in [Scheme 1-2] a] (yield: 45%).

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

[Intermediate 3-b]

(20.4 g, 0.07 mol), 4-iodophenylboronic acid (20.5 g, 0.08 mol), tetrakis (triphenylphosphine) palladium (4 g, 0.003 mol), potassium carbonate (19 g, 0.14 mol), 1,4-dioxane (100 mL), toluene (100 mL) and distilled water (40 mL). The reaction mixture was extracted with ethyl acetate and then recrystallized from dichloromethane and acetone to obtain 25.7 g (yield 80%) of [intermediate 3-b].

Synthesis of [Scheme 3-3] [Compound 13]

[Compound 13]

Compound [13] (yield 68%) was synthesized in the same manner as Intermediate 3-b except for using Intermediate 3-b obtained in Reaction Scheme 3-2 instead of Intermediate 1-c used in Reaction Scheme 1-10, .

MS (MALDI-TOF): m / z 495.17 [M ^< ⁺ &^gt;].

[ Synthetic example  4] Synthesis of Compound 24

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

[Intermediate 4-a]

Except that heptadioneonononaphthalene was used in place of 1-nitronaphthalene used in [Reaction Scheme 1-1], and pentadudeolephenylmagnesium bromide was used instead of phenylmagnesium bromide used in [Reaction Scheme 1-2]. -1] to [Scheme 1-3] to obtain [Intermediate 4-a] (yield: 45%).

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

[Intermediate 4-b]

[Intermediate 4-a] obtained from [Scheme 4-1] instead of [Intermediate 3-a] used in [Reaction Scheme 3-2] was used and instead of 4-bromo- -Dimethylphenyl) boronic acid, the intermediate 4-b was obtained (yield 75%).

[Reaction Scheme 4-3] Synthesis of [Compound 24]

Compound [24] (yield: 70%) was synthesized in the same manner as Intermediate 4-b except that Intermediate 4-b obtained in the above Reaction Scheme 4-2 was used instead of Intermediate 1-c used in Reaction Formula 1-10. .

MS (MALDI-TOF): m / z 610.31 [M ^< ⁺ &^gt;].

[ Synthetic example  5] Synthesis of Compound 31

Synthesis of [Reaction Scheme 5-1] [Intermediate 5-a]

[Intermediate 5-a]

Except that 5-nitroisoquinoline was used instead of 1-nitronaphthalene used in [Reaction Scheme 1-1], and 4-biphenylmagnesium bromide instead of phenylmagnesium bromide used in [Scheme 1-2] was used instead of [ -1] to [Scheme 1-3] to obtain [Intermediate 5-a] (yield: 48%).

Synthesis of [Reaction Scheme 5-2] [Intermediate 5-b]

[Intermediate 5-b]

[Intermediate 5-a] obtained from [scheme 5-1] instead of [intermediate 3-a] used in [scheme 3-2] was used instead of 4- Acid was used to synthesize [Intermediate 5-b] (yield: 77%).

[Reaction Scheme 5-3] Synthesis of [Compound 31]

[Compound 31] (yield: 72%) was synthesized in the same manner as Intermediate 5-b except that Intermediate 5-b obtained in the above Reaction Scheme 5-2 was used instead of Intermediate 1-c used in Reaction Formula 1-10. ≪ / RTI >

MS (MALDI-TOF): m / z 698.25 [M ^< ⁺ &^gt;

[ Synthetic example  6] Synthesis of Compound 34

Synthesis of [Reaction Scheme 6-1] [Intermediate 6-a]

[Intermediate 6-a]

Except that 2-nitronaphthalene was used instead of 1-nitronaphthalene used in [Reaction Scheme 1-1], and pentadutionalphenylmagnesium bromide was used instead of phenylmagnesium bromide used in [Reaction Scheme 1-2]. 1] to [Scheme 1-3] to obtain [Intermediate 6-a] (yield: 44%).

Synthesis of [Reaction Scheme 6-2] [Compound 34]

Compound [34] (yield 70%) was synthesized in the same manner as Intermediate 6-a, except that Intermediate 6-a obtained in the above Reaction Scheme 6-1 was used instead of Intermediate 1-c used in Reaction Formula 1-10. .

MS (MALDI-TOF): m / z 500.20 [M ⁺ ] &^lt;

[ Synthetic example  7] Synthesis of Compound 54

Synthesis of [Reaction Scheme 7-1] [Intermediate 7-a]

[Intermediate 7-a]

Synthesis was performed in the same manner except that 3-chloro-6-nitroisoquinoline was used instead of [intermediate 3-a] used in [Reaction Scheme 3-2] and phenylboronic acid was used in place of 4-iodophenylboronic acid [Intermediate 7-a] (yield: 82%).

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

[Intermediate 7-b]

Is the same as [Reaction Scheme 1-1] to [Reaction Scheme 1-3] except that [Intermediate 7-a] obtained from the above-mentioned Reaction Scheme 7-1 was used instead of 1-nitronaphthalene used in [Reaction Scheme 1-1] To obtain [intermediate 7-b] (yield: 44%).

Synthesis of [Reaction Scheme 7-3] [Intermediate 7-c]

[Intermediate 7-b] obtained from [Reaction Scheme 7-2] instead of [Intermediate 3-a] used in [Reaction Scheme 3-2] was used and instead of 4-bromopyridine-3-boron Was synthesized in the same manner as in [Intermediate 7-c] (yield: 74%).

[Synthesis 7-4] Synthesis of [Compound 54]

Compound [54] (yield: 73%) was synthesized in the same manner as Intermediate 7-c except for using [Intermediate 7-c] obtained in the above Reaction Scheme 7-3 instead of [Intermediate 1-c] .

MS (MALDI-TOF): m / z 649.23 [M ^< ⁺ &^gt;] [

[ Synthetic example  8] Synthesis of Compound 57

Synthesis of [Reaction Scheme 8-1] [Intermediate 8-a]

[Intermediate 8-a]

26.5 g (0.14 mol) of 6-nitro-1-naphthaleneol was added to 270 mL of dichloromethane and stirred. 14 g (0.18 mol) of pyridine was added and the reaction was cooled to 0 ° C. Then, 42.3 g (0.15 mol) of trifluoromethanesulfonic anhydride was slowly added dropwise and the mixture was stirred at room temperature for 1 hour. The resultant product was separated by column chromatography to obtain 34.2 g (yield 76%) of [intermediate 8-a].

Synthesis of [Reaction Scheme 8-2] [Intermediate 8-b]

[Intermediate 8-b]

Except that [Intermediate 8-a] obtained from [Reaction Scheme 8-1] instead of [Intermediate 3-a] used in [Reaction Scheme 3-2] was used and phenylboronic acid was used in place of 4-iodophenylboronic acid Synthesis was conducted in the same manner as in [Intermediate 8-b] (yield: 82%).

Synthesis of [Reaction Scheme 8-3] [Intermediate 8-c]

[Intermediate 8-c]

Is the same as [Reaction Scheme 1-1] to [Reaction Scheme 1-3] except that [Intermediate 8-b] obtained from the above-mentioned Reaction Scheme 8-2 is used instead of 1-nitronaphthalene used in [Reaction Scheme 1-1] To obtain [intermediate 8-c] (yield: 43%).

Synthesis of [Reaction Scheme 8-4] [Compound 57]

Compound [57] (yield: 73%) was synthesized in the same manner as Intermediate 8-c except for using Intermediate 8-c obtained from the above Reaction Scheme 8-3 instead of Intermediate 1-c used in Reaction Formula 1-10. .

MS (MALDI-TOF): m / z 571.20 [M ^< ⁺ &^gt;

[ Synthetic example  9] Synthesis of Compound 65

Synthesis of [Synthesis 9-1] [Synthesis of Intermediate 9-a]

[Intermediate 9-a]

Synthesis was carried out in the same manner as in [Reaction Scheme 1-1] to [Reaction Scheme 1-3] except that 9-nitrophenanthrene was used instead of 1-nitronaphthalene used in [Reaction Scheme 1-1] to obtain [Intermediate 9-a] (Yield: 56%).

Synthesis of [Synthesis 9-2] [Compound 65]

[Compound 65] (yield: 72%) was synthesized in the same manner as Intermediate 9-a, except that Intermediate 9-a obtained from the above Reaction Scheme 9-1 was used instead of Intermediate 1-c used in Reaction Formula 1-10. .

MS (MALDI-TOF): m / z 545.19 [M ^< ⁺ &^gt;

[ Synthetic example  10] Synthesis of Compound 78

Synthesis of [Synthesis 10-1] [Synthesis of Intermediate 10-a]

[Intermediate 10-a]

Except that 9-nitrophenanthrene was used instead of 1-nitronaphthalene used in [Reaction Scheme 1-1], and naphthylmagnesium bromide was used instead of phenylmagnesium bromide used in [Reaction Scheme 1-2]. ] To [Scheme 1-3] to obtain [Intermediate 10-a] (yield: 52%).

Synthesis of [Reaction Scheme 10-2] [Intermediate 10-b]

[Intermediate 10-a] obtained from [Scheme 10-1] instead of [Intermediate 3-a] used in [Reaction Scheme 3-2] was used instead of 4-iodophenylboronic acid and 5-chloropyrazine-2-boronic acid Was synthesized in the same manner as [Intermediate 10-b] (yield: 70%).

Synthesis of [Reaction formula 10-3] [Compound 78]

Compound [78] (yield 70%) was synthesized in the same manner as Intermediate 10-b except for using [Intermediate 10-b] obtained from the above-mentioned scheme 10-2 instead of Intermediate 1-c used in [Scheme 1-10] .

MS (MALDI-TOF): m / z 673.23 [M ^< ⁺ &^gt;

[ Synthetic example  11] Synthesis of Compound 85

Synthesis of [Intermediate 11-a]

[Intermediate 1-c] obtained from [Scheme 1-3] instead of [Intermediate 3-a] used in [Reaction Scheme 3-2] was used instead of 4-iodophenylboronic acid and 4- Was synthesized in the same manner as in [Intermediate 11-a] (yield 77%).

Synthesis of [Reaction Scheme 11-2] [Compound 85]

[Compound 85] (yield: 72%) was synthesized in the same manner as Intermediate 11-a, except that [Intermediate 11-a] obtained from the above-mentioned Reaction Scheme 11-1 was used instead of [Intermediate 1-c] .

MS (MALDI-TOF): m / z 647.24 [M ^< ⁺ &^gt;].

[ Example  1 to 11] Production of organic light emitting diode

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. And then mounted on the vacuum chamber was such that the base pressure is ^{1 × 10 -6 torr DNTPD (700Å} ) an organic material on the ITO substrate, α-NPB (300Å), the compound + (piq) ₂ produced according to the present invention The films were deposited in the order of Ir (acac) (10%) (300 Å), Alq ₃ (350 Å), LiF (5 Å) and Al (1,000 Å).

The DNTPD, α-NPB, (piq ) 2 Ir (acac), Alq 3 structure is as follows.

[DNTPD] [[alpha] -NPB]

_{[(piq) 2 Ir (acac} )] [Alq 3]

[ Comparative Example  One]

The organic light emitting diode device for Comparative Example 1 was the same as Example 1 except that CBP, which is generally used as a phosphorescent host material instead of the compound prepared by the present invention, was used in the device structures of Examples 1 to 11 The structure of the CBP is as follows.

[CBP]

The voltage, luminance, color coordinates, and lifetime of the organic electroluminescent device manufactured according to Examples 1 to 11 and Comparative Example 1 were measured, and the results are shown in Table 1 below.

division Host Dopant Voltage (V) Brightness (Cd / m2) CIEx CIEy Example 1 Compound 1 (piq) < / RTI > ₂ Ir (acac) 4.0 1065 0.671 0.329 Example 2 Compound 2 (piq) < / RTI > ₂ Ir (acac) 4.0 1204 0.676 0.322 Example 3 Compound 13 (piq) < / RTI > ₂ Ir (acac) 3.9 1142 0.670 0.326 Example 4 Compound 24 (piq) < / RTI > ₂ Ir (acac) 3.9 1248 0.676 0.325 Example 5 Compound 31 (piq) < / RTI > ₂ Ir (acac) 4.0 1113 0.669 0.323 Example 6 Compound 34 (piq) < / RTI > ₂ Ir (acac) 4.0 1200 0.674 0.324 Example 7 Compound 54 (piq) < / RTI > ₂ Ir (acac) 3.9 1155 0.676 0.323 Example 8 Compound 57 (piq) < / RTI > ₂ Ir (acac) 4.0 1086 0.674 0.326 Example 9 Compound 65 (piq) < / RTI > ₂ Ir (acac) 4.1 1059 0.674 0.329 Example 10 Compound 78 (piq) < / RTI > ₂ Ir (acac) 4.0 1095 0.667 0.332 Example 11 Compound 85 (piq) < / RTI > ₂ Ir (acac) 3.9 1167 0.674 0.326 Comparative Example 1 CBP (piq) < / RTI > ₂ Ir (acac) 7.9 350 0.667 0.324

As shown in Table 1, the organic compound obtained according to the present invention has much lower driving voltage and luminance than CBP among host materials which are widely used as a phosphorescent host material.

Claims (9)

An organic light-emitting compound represented by the following Formula 1:
[Chemical Formula 1]

In the above formula (1)
A is selected from the following formulas (I) to (III)
[Chemical Formula I] [Chemical Formula II] [Chemical Formula III]

X ₁ to X ₈ are the same or different and are each independently N or CR ₁₂ ,
R ₁ to R ₁₂ are the same or different from each other and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a hydroxyl group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C2-C50 hetero aryl group, a substituted or unsubstituted C3-C30 cycloalkyl group, A substituted or unsubstituted aryloxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms , A substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms. A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms and a substituted or unsubstituted arylsilyl group having 5 to 50 carbon atoms,
L is a single bond or a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylene group having 2 to 30 carbon atoms A substituted or unsubstituted C2-C30 alkynylene group, a substituted or unsubstituted C3-C30 A substituted or unsubstituted arylene group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, n is an integer of 0 to 3, and n is an integer of 2 or more A plurality of Ls may be the same or different from each other,
R ₁ to R ₁₂ and L may combine with each other or adjacent substituents to form a single alicyclic or aromatic ring or polycyclic ring, and the carbon atom of the ring formed may be any one selected from N, S, O and P Lt; / RTI > or more heteroatoms,
'*' In the above formulas (I) to (III) means a site bound to the above formula (I). The method according to claim 1,
Wherein L is any one selected from the following structural formulas A1 to A16:
[Structural formula A1] [Structural formula A2] [Structural formula A3] [Structural formula A4]

[Structural formula A5] [Structural formula A6] [Structural formula A7] [Structural formula A8]

[Structural formula A9] [Structural formula A10] [Structural formula A11] [Structural formula A12]

[Structural formula A13] [Structural formula A14] [Structural formula A15] [Structural formula A16]

In the above structural formulas A1 to A16, hydrogen or deuterium may be bonded to the carbon of the aromatic ring in each structural formula. The method according to claim 1,
R ₁ to R ₁₂ And L are each independently 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 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an alkynyl group having 1 to 20 carbon atoms, An aryl group having 5 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 5 to 24 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, Group, an alkylamine group having 1 to 20 carbon atoms, and an arylamine group having 6 to 24 carbon atoms. The method according to claim 1,
The organic luminescent compound according to claim 1, wherein the compound represented by formula (1) is selected from the following compounds [1] to [88]
[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]

A first electrode; A second electrode; And at least one organic layer interposed between the first electrode and the second electrode,
Wherein the organic layer comprises at least one organic electroluminescent compound represented by Formula 1 according to Claim 1. 6. The method of claim 5,
Wherein the organic layer includes one or more layers selected from a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer. 6. The method of claim 5,
Wherein the organic layer interposed between the first electrode and the second electrode comprises a light emitting layer. 8. The method of claim 7,
Wherein the light emitting layer comprises a host compound and a dopant compound, and the organic light emitting compound of Formula 1 according to Claim 1 is used as a host, and the light emitting layer further comprises at least one dopant compound. An electroluminescent device. 6. The method of claim 5,
Wherein the organic layer comprises at least one organic light emitting layer emitting red, green or blue light, and emits white light.

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