KR102191020B1 - Heterocyclic com pounds and organic light-emitting diode including the same - Google Patents

Abstract

The present invention relates to a novel heterocyclic compound and an organic electroluminescent device comprising the same as a light emitting material, and more particularly, to a heterocyclic compound having excellent emission characteristics such as driving voltage, luminous efficiency and lifetime, and organic electroluminescence comprising the same It relates to the device. Since the heterocyclic compound of the present invention is stable compared to conventional materials and has excellent luminescence characteristics in driving voltage or current efficiency, an organic electroluminescent device including the same can be driven at a low voltage and improve luminous efficiency.

Description

Heterocyclic com pounds and organic light-emitting diode including the same}

The present invention relates to a novel heterocyclic compound and an organic electroluminescent device comprising the same as a light emitting material, and more particularly, to a heterocyclic compound having excellent emission characteristics such as driving voltage, luminous efficiency and lifetime, and organic electroluminescence comprising the same It relates to the device.

Recently, organic light emitting devices capable of low voltage driving by self-luminous type have superior viewing angles and contrast ratios, compared to LCD (liguid crystal displays), which are the mainstream of flat panel display devices, do not require a backlight, and are lightweight and thin. It is attracting attention as a next-generation display device because it is advantageous in terms of power and has a wide color reproduction range.

Organic light emitting diodes (OLEDs) are devices that emit light while electrons and holes form a pair and then disappear when charge is injected into an organic light emitting layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode). to be. The organic electroluminescent device usually has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device. For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. . In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.

The organic electroluminescent device not only can form the device on a flexible transparent substrate such as plastic, but also at a voltage lower than 10V compared to a plasma display panel or an inorganic electroluminescent (EL) display. It can be driven, consumes relatively little power, and has the advantage of excellent color. In addition, since the organic light emitting diode can display three colors of green, blue, and red, it is a target of many people's interest as a next-generation rich color display device.

In order to fully exhibit these excellent features, materials that make up the organic material layer in the device, such as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, etc., must be supported by stable and efficient materials. Until now, the development of a stable and efficient organic material layer material for an organic light emitting device has not been sufficiently carried out. Therefore, the development of new materials continues to be required.

Accordingly, an object of the present invention is to provide a novel heterocyclic compound capable of simultaneously realizing low voltage driving of the device, improved luminous efficiency, and long life characteristics when employed in an organic material layer in an organic light emitting device, and an organic light emitting device including the same.

The present invention provides a heterocyclic compound represented by the following [Chemical Formula 1] in order to solve the above problems.

[Formula 1]

In addition, the present invention provides an organic electroluminescent device having an anode, a cathode, and a layer interposed between the anode and the cathode and including a heterocyclic compound represented by [Chemical Formula 1].

A description of the structure and substituent for [Chemical Formula 1] will be described later.

Since the organic light-emitting compound according to the present invention is stable compared to conventional materials and has excellent luminescence characteristics in driving voltage, luminous efficiency, and lifespan, an organic light-emitting device including the same enables a long-life device and at the same time enables low voltage driving. And improve luminous efficiency.

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

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

The present invention is a light emitting layer host material having improved light emission characteristics such as driving voltage and current efficiency of an organic light emitting device, and X ₁ to X ₁₀ , R ₁ , R ₂ , L, for heterocyclic compounds represented by the following formula (1). Ar and various substituents are combined to provide compounds:

[Formula 1]

In the above [Formula 1],

A ₁ to A ₄ are each independently C or -CH, and in this case, when A is C, two adjacent A may be bonded to L to form a condensed ring.

이고, Y 및 Z는 각각 독립적으로 단일결합이거나, -CR₂R₃-또는 -NR₂-이다.L is

And Y and Z are each independently a single bond, or -CR ₂ R ₃ -or -NR ₂ -.

Ar may be a substituted or unsubstituted aryl group having 6 to 40 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and R ₁ to R ₃ And X ₁ to X ₁₆ are each independently 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 It may be one or more selected from the group consisting of a salt thereof, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms have.

l, n and m are each independently an integer of 0 to 3.

In addition, Ar, R ₁ and R ₃ , X ₁ and X ₁₆ are each independently 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, Alkynyl group having 1 to 20 carbon atoms, halogenated alkyl group having 1 to 20 carbon atoms, aryl group having 5 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, alkoxy group having 1 to 20 carbon atoms, aryloxy group having 5 to 24 carbon atoms, It may be further substituted with one or more substituents selected from an alkylsilyl group having 1 to 20 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, and the substituent May be bonded to each other to form a saturated or unsaturated ring.

According to one embodiment of the present invention, Ar may be any one linking group selected from the following [Structural Formula A1] to [Structural Formula 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 [Structural Formulas A1] to [Structural Formulas A16], hydrogen or deuterium may be bonded to the carbon of the aromatic ring in each of the structural formulas.

'Substituted' in the'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 20 carbon atoms, alkenyl group having 1 to 20 carbon atoms, alkynyl group having 1 to 20 carbon atoms, Halogenated alkyl group having 1 to 20 carbon atoms, aryl group having 5 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, alkoxy group having 1 to 20 carbon atoms, aryloxy group having 5 to 24 carbon atoms, alkylsilyl group having 1 to 20 carbon atoms , It means to be further substituted with one or more substituents selected from 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, and the substituents are bonded to each other with an adjacent substituent To form saturated or unsaturated rings.

In addition, the range of carbon atoms of the alkyl group or aryl group in the'substituted or unsubstituted alkyl group having 1 to 30 carbon atoms' and'substituted or unsubstituted aryl group having 5 to 50 carbon atoms' consider the portion where the substituent is substituted It does not mean the total number of carbon atoms constituting the alkyl moiety or the aryl moiety when viewed as unsubstituted. For example, a phenyl group in which a butyl group is substituted in the para position corresponds to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

The aryl group 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 members, preferably 5 or 6 members, and When the aryl group has a substituent, it may be fused with neighboring substituents to form an additional ring.

Specific examples of the aryl group include phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, 4-methylbiphenyl group, 4 -Ethylbiphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, 2-naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group, anthryl group, phenanthryl group, And aromatic groups such as pyrenyl group, indenyl, fluorenyl group, tetrahydronaphthyl group, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, and the like.

At least one hydrogen atom in the aryl group is a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH(R), -N(R')(R"), R 'And R'are each independently an alkyl group having 1 to 10 carbon atoms, in this case referred to as an "alkylamino group"), an amidino group, 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, Halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 1 to 24 carbon atoms, alkynyl group having 1 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 6 to 24 carbon atoms, carbon number It may be substituted with a 2 to 24 heteroaryl group or a C 2 to 24 heteroarylalkyl group.

The heteroaryl group as a substituent used in the present invention may be any one selected from the following [Structural Formula 1] to [Structural Formula 6].

[Structural Formula 1] [Structural Formula 2] [Structural Formula 3]

[Structural Formula 4] [Structural Formula 5] [Structural Formula 6]

In the [Structural Formula 1] to [Structural Formula 6],

T ₁ to T ₈ are the same as or different from each other, and each independently, may be any one selected from C (R ₄₁ ), C (R ₄₂ ) (R ₄₃ ), N, N (R ₄₄ ), O and S, and , The R ₃₁ to R ₄₄ are the same 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 cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted It may be any one selected from a C5 to C30 aryl group and a substituted or unsubstituted C2 to C30 heteroaryl group having O, N, S or P as a hetero atom, and each of [Structural Formula 1] to In [Structural Formula 6], the R ₃₁ to R ₄₄ One of them may form a single bond with the substituent of [Chemical Formula 1].

In addition, the [Structural Formula 3] may include a compound represented by the following [Structural Formula 3-1] by a resonance structure according to the movement of electrons.

[Structural Formula 3-1]

In the [Structural Formula 3-1], T ₁ to T ₅ and R ₃₃ and R ₃₄ are the same as defined above.

In addition, according to a preferred embodiment of the present invention, the [Structural Formula 1] to [Structural Formula 6] may be selected from the following [Structural Formula 7].

[Structural Formula 7]

In [Structural 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, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 2 to 20 alkynyl group, substituted or unsubstituted C 3 to C 30 cycloalkyl group, substituted or unsubstituted C 5 to C 30 cycloalkenyl group, substituted or unsubstituted C 1 to C 30 alkoxy group, substituted or unsubstituted A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl thioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkyl having 1 to 30 carbon atoms The group consisting of an amine group, a substituted or unsubstituted aryl group having 5 to 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, a halogen group Any one selected from among, m is an integer of 1 to 11, and when m is 2 or more, a plurality of Xs are the same as or different from each other, and any one of the at least one X represents a substituent group and a single bond of It can be achieved.

Specific examples of the alkyl group as a substituent used in the present invention include methyl group, ethyl group, propyl group, isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, iso-amyl group, hexyl group, heptyl group , Octyl group, stearyl group, trichloromethyl group, trifluoromethyl group, etc., and at least one hydrogen atom of the alkyl group is a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a trifluoromethyl group, a silyl group (In this case, referred to as "alkylsilyl group"), a substituted or unsubstituted amino group (-NH ₂ , -NH(R), -N(R')(R"), wherein R, R'and R" are each Independently, it is an alkyl group having 1 to 24 carbon atoms (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, an alkyl group having 1 to 24 carbon atoms, and Halogenated alkyl group, C2-C24 alkenyl group, C2-C24 alkynyl group, C1-C24 heteroalkyl group, C5-C24 aryl group, C6-C24 arylalkyl group, C3-C24 hetero It may be substituted with an aryl group or a heteroarylalkyl group having 3 to 24 carbon atoms.

Specific examples of the alkoxy group as a substituent used in the present invention include a methoxy group, an ethoxy group, a propoxy group, an isobutyloxy group, a sec-butyloxy group, a pentyloxy group, an iso-amyloxy group, a hexyloxy group, and the like. May be substituted with the same substituent as in the case of the alkyl group.

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

The aryloxy group used in the present invention refers to an -O- aryl radical, wherein the aryl group is as defined above, and specific examples include phenoxy, naphthoxy, anthracenyloxy, phenanthrenyloxy, fluorenyl Oxy, indenyloxy, and the like, and one or more hydrogen atoms contained in the aryloxy group may be further substituted.

Specific examples of the silyl group as a substituent used in the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethyl Furylsilyl, etc. are mentioned.

Specific examples of the alkenyl group used in the present invention represent a linear or branched alkenyl group, 3-pentenyl group, 4-hexenyl group, 5-heptenyl group, 4-methyl-3-pentenyl group, 2,4 -Dimethyl-pentenyl group, 6-methyl-5-heptenyl group, 2,6-dimethyl-5-heptenyl group, etc. are mentioned.

The present invention is not limited by a specific example of the heterocyclic compound according to Formula 1 having the structure as described above, but may specifically be any one of the compounds represented by the following [Chemical Formula 2] to [Chemical Formula 213] have.

[Formula 2] [Formula 3] [Formula 4] [Formula 5]

[Formula 6] [Formula 7] [Formula 8] [Formula 9]

[Formula 10] [Formula 11] [Formula 12] [Formula 13]

[Formula 14] [Formula 15] [Formula 16] [Formula 17]

[Formula 18] [Formula 19] [Formula 20] [Formula 21]

[Formula 22] [Formula 23] [Formula 24] [Formula 25]

[Formula 26] [Formula 27] [Formula 28] [Formula 29]

[Formula 30] [Formula 31] [Formula 32] [Formula 33]

[Formula 34] [Formula 35] [Formula 36] [Formula 37]

[Formula 38] [Formula 39] [Formula 40] [Formula 41]

[Formula 42] [Formula 43] [Formula 44] [Formula 45]

[Chemical Formula 46] [Chemical Formula 47] [Chemical Formula 48] [Chemical Formula 49]

[Formula 50] [Formula 51] [Formula 52] [Formula 53]

[Formula 54] [Formula 55] [Formula 56] [Formula 57]

[Chemical Formula 58] [Chemical Formula 59] [Chemical Formula 60] [Chemical Formula 61]

[Formula 62] [Formula 63] [Formula 64] [Formula 65]

[Formula 66] [Formula 67] [Formula 68] [Formula 69]

[Formula 70] [Formula 71] [Formula 72] [Formula 73]

[Formula 74] [Formula 75] [Formula 76] [Formula 77]

[Chemical Formula 78] [Chemical Formula 79] [Chemical Formula 80] [Chemical Formula 81]

[Formula 82] [Formula 83] [Formula 84] [Formula 85]

[Formula 86] [Formula 87] [Formula 88] [Formula 89]

[Formula 90] [Formula 91] [Formula 92] [Formula 93]

[Formula 94] [Formula 95] [Formula 96] [Formula 97]

[Formula 98] [Formula 99] [Formula 100] [Formula 101]

[Formula 102] [Formula 103] [Formula 104] [Formula 105]

[Formula 106] [Formula 107] [Formula 108] [Formula 109]

[Formula 110] [Formula 111] [Formula 112] [Formula 113]

[Formula 114] [Formula 115] [Formula 116] [Formula 117]

[Chemical Formula 118] [Chemical Formula 119] [Chemical Formula 120] [Chemical Formula 121]

[Formula 122] [Formula 123] [Formula 124] [Formula 125]

[Formula 126] [Formula 127] [Formula 128] [Formula 129]

[Formula 130] [Formula 131] [Formula 132] [Formula 133]

[Formula 134] [Formula 135] [Formula 136] [Formula 137]

[Formula 138] [Formula 139] [Formula 140] [Formula 141]

[Formula 142] [Formula 143] [Formula 144] [Formula 145]

[Formula 146] [Formula 147] [Formula 148] [Formula 149]

[Formula 150] [Formula 151] [Formula 152] [Formula 153]

[Formula 154] [Formula 155] [Formula 156] [Formula 157]

[Formula 158] [Formula 159] [Formula 160] [Formula 161]

[Formula 162] [Formula 163] [Formula 164] [Formula 165]

[Formula 166] [Formula 167] [Formula 168] [Formula 169]

[Chemical Formula 170] [Chemical Formula 171] [Chemical Formula 172] [Chemical Formula 173]

[Formula 174] [Formula 175] [Formula 176] [Formula 177]

[Formula 178] [Formula 179] [Formula 180] [Formula 181]

[Formula 182] [Formula 183] [Formula 184] [Formula 185]

[Formula 186] [Formula 187] [Formula 188] [Formula 189]

[Formula 190] [Formula 191] [Formula 192] [Formula 193]

[Formula 194] [Formula 195] [Formula 196] [Formula 197]

[Formula 198] [Formula 199] [Formula 200] [Formula 201]

[Chemical Formula 202] [Chemical Formula 203] [Chemical Formula 204] [Chemical Formula 205]

[Formula 206] [Formula 207] [Formula 208] [Formula 209]

[Formula 210] [Formula 211] [Formula 212] [Formula 213]

In addition, the present invention provides an organic electroluminescent device having an anode, a cathode, a layer interposed between the anode and the cathode, and including a heterocyclic compound represented by [Chemical Formula 1].

At this time, the layer containing the heterocyclic compound is preferably a light emitting layer between the anode and the cathode, and between the anode and the cathode, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer are used. It may further include one or more layers selected from the group consisting of.

In addition, according to another embodiment of the present invention, it is preferable that the thickness of the emission layer is 50 to 2,000 Å, and the emission layer may further include a material of the following structural formula.

[Ir(ppy) ₃ ]

[Ir(chpy) ₃ ]

[Ir(mchpy) ₃ ]

As a specific example, a hole transport layer (HTL) may be additionally stacked, and an electron transport layer (ETL) may be additionally stacked between the cathode and the organic light emitting layer. The transport layer is laminated to make it easier to inject holes from the anode, and an electron donating molecule having a small ionization potential is used as a material for the hole transport layer, mainly diamine, triamine or tetraamine derivatives having triphenylamine as a basic skeleton. Is used a lot.

In the present invention, as the material of the hole transport layer, which is commonly used in the art, is not particularly limited, and 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'-diphenyl benzidine (a-NPD), and the like can be used.

A hole injection layer (HIL) may be additionally stacked under the hole transport layer, and the hole injection layer material is also not particularly limited as long as it is commonly used in the art. For example, CuPc (copper phthalocyanine) or Starburst type amines TCTA (4,4',4''-tri(N -carbazolyl) triphenyl-amine), m-MTDATA(4,4',4'' -tris-(3-methyl phenylphenylamino)triphenylamine) can be used.

In addition, the electron transport layer used in the organic light emitting device according to the present invention smoothly transports electrons supplied from the cathode to the organic light emitting layer and inhibits the movement of holes that could not be combined in the organic light emitting layer, thereby recombining in the light emitting layer. It serves to increase.

The electron transport layer material is not particularly limited and may be used as long as it is commonly used in the art. For example, an oxadiazole derivative such as PBD, BMD, BND, or Alq ₃ may be used.

On the other hand, on the top of the electron transport layer, an electron injecting layer (EIL) that facilitates electron injection from the cathode and ultimately improves power efficiency may be further stacked. The material of the electron injection layer Also, as long as it is commonly used in the art, it may be used without particular limitation, and for example, materials such as LiF, NaCl, CsF, Li ₂ O, and BaO may be used.

The organic electroluminescent device according to the present invention may be used in a display device, a display device, and a single color or white lighting device.

1 is a cross-sectional view showing the structure of an organic light emitting 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 light emitting layer 50, an electron transport layer 60, and a cathode 80, and if necessary, the hole injection layer 30 and An electron injection layer 70 may be further included, and in addition to that, a first or second intermediate layer may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

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

The hole injection layer 30 is formed by vacuum thermal evaporation or spin coating on the anode 20 electrode. Then, a hole transport layer material is vacuum thermally evaporated or spin coated on the hole injection layer 30 to form the hole transport layer 40.

Subsequently, an 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 vacuum deposition or spin coating to form a thin film. can do. 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 because when holes pass through the organic light emitting layer and flow into the cathode, the life and efficiency of the device are reduced. . In this case, the hole blocking material to be used is not particularly limited, but must have an electron transport ability and an ionization potential higher than that of the light emitting compound, and representatively, BAlq, BCP, TPBI, etc. may be used.

After depositing the electron transport layer 60 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 the cathode 80 electrode. Here, the cathode-forming metal is lithium (Li), magnesium (Mg), aluminum (Al), aluminum-ridium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver ( Mg-Ag) or the like may be used, and in order to obtain a top light emitting device, a transmissive cathode using ITO or IZO may be used.

In addition, according to another embodiment of the present invention, at least one layer 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 is a monomolecular deposition method or a solution process. The organic electroluminescent device according to the present invention may be used in a display device, a display device, and a single color or white lighting device.

Hereinafter, the present invention will be described in more detail with reference to preferred manufacturing examples and examples. However, it will be apparent to those of ordinary skill in the art that the following Preparation Examples and Examples are only for describing the present invention in more detail, and that the scope of the present invention is not limited by the following Preparation Examples and Examples. will be.

Manufacturing example

< Manufacturing example 1> Preparation of the compound represented by Formula 2

Step 1: Preparation of the compound represented by formula 1-a

As shown in Scheme 1 below, a compound represented by Formula 1-a was prepared.

[Scheme 1]

After adding ethyl 2-amino-5-bromobenzoate (400.0 g, 1639 mmol) and 4000 ml of tetrahydrofuran to a round bottom flask, it was cooled to 0 °C, and then methyl magnesium bromide (3.0 M in diethyl ether 1912). Ml, 5736 mmol) was added dropwise and refluxed for 4 hours, and the reaction was terminated. After cooling to room temperature, 10% ammonium chloride aqueous solution was added, and the mixture was stirred for 2 hours, and the layers were separated to obtain an organic layer and concentrated under reduced pressure to obtain 280 g (yield 74.3%) of a compound represented by Formula 1-a.

Step 2: Preparation of the compound represented by Formula 1-b

As shown in Scheme 2 below, a compound represented by Formula 1-b was prepared.

[Scheme 2]

In a round bottom flask, the compound represented by formula 1-a obtained from Scheme 1 (280 g, 1217 mmol), 1,2-dibromobenzene (287 g, 1217 mmol), palladium acetate (5.5 g, 24 mmol), Xant Phosphorus (28.2 g, 49 mmol), cesium carbonate (555 g, 1703 mmol), and 2870 ml of toluene were added, followed by refluxing for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered, toluene was concentrated under reduced pressure to remove the solvent, and the concentrate was subjected to column chromatography using ethyl acetate and hexane as developing solvents, and 272 g of the compound represented by Formula 1-b (yield 58.1) %).

Step 3: Preparation of the compound represented by 1-c

As shown in Scheme 3 below, a compound represented by the compound represented by Formula 1-c was prepared.

[Scheme 3]

In a round bottom flask, the compound represented by 1-b (272 g, 706 mmol) obtained from Scheme 2 was dissolved in 5440 ml of phosphoric acid and reacted for 12 hours. After completion of the reaction, the reaction solution was poured into an excess of water to form a solid and filtered to obtain 150 g (yield 57.9%) of a compound represented by Formula 1-c.

Step 4: Preparation of the compound represented by 1-d

As shown in Scheme 4 below, a compound represented by the compound represented by Formula 1-d was prepared.

[Scheme 4]

In a round bottom flask, the compound represented by 1-c obtained from Scheme 3 (150 g, 409 mmol), iodobenzene (166.7 g, 817 mmol), copper (77.8 g, 1226 mmol), potassium carbonate (225.9 g, 1635) mmol), 18-crown-6 (21.6 g, 82 mmol), and 1500 ml of 1,2-dichlorobenzene were added, followed by refluxing for 72 hours. After the reaction was completed, it was filtered and 1,2-dichlorobenzene was concentrated. After cooling to room temperature, normal hexane was added to form a solid, filtered, recrystallized with tetrahydrofuran and acetone, and dried to obtain 120 g (yield 66.3%) of the compound represented by Formula 1-d.

Step 5: Preparation of the compound represented by Formula 1-e

As shown in Scheme 5 below, a compound represented by Formula 1-e was prepared.

[Scheme 5]

In a round bottom flask, the compound represented by 1-d obtained from Scheme 4 (120 g, 271 mmol), tetrakistriphenylphosphine palladium 12.5 g (11 mmol), potassium acetate 39.8 g (406 mmol), dimethylformamide After 1200 ml was added, it was refluxed for 12 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure after filtering. As a result of recrystallization from toluene and hexane and drying, 35 g (yield 35.7%) of a compound represented by 1-e was obtained.

Step 6: Preparation of the compound represented by Formula 1-f

As shown in Scheme 6 below, a compound represented by Formula 1-f was prepared.

[Scheme 6]

Except for using 2-bromoaniline instead of the compound represented by Formula 1-a used in Scheme 2, and using the compound represented by Formula 1-e prepared in Scheme 5 instead of 1,2-dibromobenzene Followed the same method to obtain 25 g (yield 57.1%) of a compound represented by Formula 1-f.

Step 7: Preparation of the compound represented by Formula 1-g

As shown in Scheme 7 below, a compound represented by Formula 1-g was prepared.

[Scheme 7]

In a round bottom flask, the compound represented by 1-f obtained from Scheme 6 (25 g, 55 mmol), tetrakistriphenylphosphine palladium 2.6 g (2 mmol), potassium acetate 8.1 g (83 mmol), dimethylformamide After adding 250 ml, it was refluxed for 12 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure after filtering. After recrystallization from toluene and hexane and drying, 6 g (yield 29.2%) of the compound represented by Chemical Formula 1-g was obtained.

Step 8: Preparation of the compound represented by Formula 2

As shown in Scheme 8 below, a compound represented by Formula 2 was prepared.

[Scheme 8]

60% sodium hydride (1.1 g, 27 mmol) and 90 ml of dimethylformamide were added to a round bottom flask, stirred, and then a compound represented by 1-g obtained from Scheme 7 (6.0 g, 16 mmol) was added. After addition, it was stirred for 1 hour. 2-chloro-4,6-diphenyl-1,3,5-triazine (5.6 g, 21 mmol) was dissolved in 60 ml of dimethylformamide, added dropwise to the reaction solution, and stirred. When the reaction was completed, water was poured, filtered, and recrystallized from 1,2-dichlorobenzene to obtain 3.0 g (yield 30.8%) of the compound represented by Chemical Formula 2.

MS [M] ⁺ 604

< Manufacturing example 2> Preparation of the compound represented by Formula 3

Step 1: Preparation of the compound represented by Formula 2-a

As shown in Scheme 9 below, a compound represented by Formula 2-a was prepared.

[Scheme 9]

Except for using ethyl 2-amino benzoate instead of 2-bromoaniline used in Scheme 6, the same method was carried out to obtain 28.5 g (yield 66.1%) of a compound represented by Formula 2-a.

Step 2: Preparation of the compound represented by 2-b

As shown in Scheme 10 below, a compound represented by Formula 2-b was prepared.

[Scheme 10]

Compound 20.5 represented by Formula 2-b was carried out in the same manner except that the compound represented by 2-a prepared in Scheme 9 was used instead of ethyl 2-amino-5-bromobenzoate used in Scheme 1 g (yield 74.3%) was obtained.

Step 3: Preparation of the compound represented by 2-c

As shown in Scheme 11 below, a compound represented by Formula 2-c was prepared.

[Scheme 11]

Except for using the compound represented by Formula 2-b prepared in Scheme 10 instead of the compound represented by Formula 1-b used in Scheme 3, 7.5 g of the compound represented by Formula 2-c ( Yield 38.2%) was obtained.

Step 4: Preparation of the compound represented by Formula 3

As shown in Scheme 12 below, a compound represented by Formula 3 was prepared.

[Scheme 12]

Except for using the compound represented by 2-c prepared in Scheme 11 instead of the compound represented by Formula 1-g used in Scheme 8, 4.5 g of the compound represented by Formula 3 (yield 38.5% ).

MS [M] ⁺ 646

< Manufacturing example 3> Preparation of the compound represented by Formula 35

Step 1: Preparation of the compound represented by the formula 3-a

As shown in Scheme 13 below, a compound represented by Formula 3-a was prepared.

[Scheme 13]

After adding ethyl 2-amino-5-bromobenzoate (400.0 g, 1639 mmol) and 4000 ml of tetrahydrofuran to a round bottom flask, it was cooled to 0 °C, and then methyl magnesium bromide (3.0 M in diethyl ether 1912). Ml, 5736 mmol) was added dropwise and refluxed for 4 hours to terminate the reaction. After cooling to room temperature, 10% ammonium chloride aqueous solution was added, and the mixture was stirred for 2 hours, and the layers were separated to obtain an organic layer and concentrated under reduced pressure to obtain 280 g (yield 74.3%) of a compound represented by Chemical Formula 3-a.

Step 2: Preparation of the compound represented by Formula 3-b

As shown in Scheme 14 below, a compound represented by Formula 3-b was prepared.

[Scheme 14]

In a round bottom flask, the compound represented by formula 3-a obtained from Scheme 13 (280 g, 1215 mmol), ethyl 2-bromo benzoate (232 g, 1013 mmol), palladium acetate (4.6 g, 20 mmol), Xant Phosphorus (23.4 g, 41 mmol), cesium carbonate (4626 g, 1418 mmol), and 2320 ml of toluene were added, followed by refluxing for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered, toluene was concentrated under reduced pressure to remove the solvent, and the concentrated solution was subjected to column chromatography using ethyl acetate and hexane as developing solvents, and 272 g of the compound represented by Formula 3-b (yield 71) %).

Step 3: Preparation of the compound represented by Formula 3-c

As shown in Scheme 15 below, a compound represented by Formula 3-c was prepared.

[Scheme 15]

In a round-bottom flask, the compound represented by Formula 3-b (272 g, 719 mmol) obtained from Scheme 14 was dissolved in 5440 ml of phosphoric acid and reacted for 12 hours. After the reaction was completed, the reaction solution was poured into an excess of water to form a solid and filtered to obtain 120 g (yield 46.3%) of a compound represented by Chemical Formula 3-c.

Step 4: Preparation of the compound represented by Formula 3-d

As shown in Scheme 16 below, a compound represented by Formula 3-d was prepared.

[Scheme 16]

Compound represented by Formula 3-d by performing the same method except for using the compound represented by Formula 3-c prepared in Scheme 15 instead of ethyl 2-amino-5-bromobenzoate used in Scheme 13 85 g (yield 73.7%) was obtained.

Step 4: Preparation of a compound represented by Formula 3-e

As shown in Scheme 17 below, a compound represented by Formula 3-e was prepared.

[Scheme 17]

Except for using the compound represented by Formula 3-d prepared in Scheme 16 instead of the compound represented by Formula 1-c used in Scheme 4, the same method was performed, and 68 g of the compound represented by Formula 3-e ( Yield 65.6%) was obtained.

Step 6: Preparation of a compound represented by Formula 3-f

As shown in Scheme 18 below, a compound represented by Formula 3-f was prepared.

[Scheme 18]

Except for using the compound represented by Formula 3-e prepared in Scheme 17 instead of the compound represented by Formula 1-b used in Scheme 3, 35 g of the compound represented by Formula 3-f ( Yield 53.8%) was obtained.

Step 7: Preparation of the compound represented by Formula 3-g

As shown in Scheme 19 below, a compound represented by Chemical Formula 3-g was prepared.

[Scheme 19]

Except for using the compound represented by Formula 3-f prepared in Scheme 18 instead of the compound represented by Formula 1-e used in Scheme 9, the same method was carried out, and 29 g of the compound represented by Formula 3-g ( Yield 68.6%) was obtained.

Step 8: Preparation of a compound represented by Formula 3-h

As shown in Scheme 20 below, a compound represented by Formula 3-h was prepared.

[Scheme 20]

Except for using the compound represented by Formula 3-g prepared in Scheme 19 instead of the compound represented by Formula 2-a used in Scheme 10, 22 g of the compound represented by Formula 3-h ( Yield 78.1%) was obtained.

Step 9: Preparation of the compound represented by Formula 3-i

As shown in Scheme 21 below, a compound represented by Formula 3-i was prepared.

[Scheme 21]

Except for using the compound represented by Formula 3-h prepared in Scheme 20 instead of the compound represented by Formula 2-b used in Scheme 11, 8 g of the compound represented by Formula 3-i ( Yield 37.8%) was obtained.

Step 10: Preparation of a compound represented by Chemical Formula 35

As shown in Scheme 22 below, a compound represented by Chemical Formula 35 was prepared.

[Scheme 22]

Except for using the compound represented by Formula 3-i prepared in Scheme 21 instead of the compound represented by Formula 2-c used in Scheme 12, 4 g of the compound represented by Formula 35 (yield 33.2 %).

MS [M] ⁺ 688

< Manufacturing example 4> Preparation of the compound represented by Formula 54

Step 1: Preparation of the compound represented by formula 4-a

As shown in Scheme 23 below, a compound represented by Formula 4-a was prepared.

[Scheme 23]

After adding 1-bromo-3-iodobenzene (60.0 g, 212 mmol) and 480 ml of tetrahydrofuran to a round bottom flask, the temperature was maintained at -78 °C in nitrogen state, and 1.6M normal after 30 minutes. 126 ml (202 mmol) of butyllithium was slowly added dropwise. After 1 hour, a solution in which 62.4 g (233 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine was dissolved in 250 ml of tetrahydrofuran was slowly added dropwise, stirred for 30 minutes, and then the temperature was raised to room temperature. I put it up. After stirring at room temperature for about 1 hour, an aqueous 2N (normal) hydrochloric acid solution was added dropwise to the reaction solution until it became acid. The extracted organic layers were collected, concentrated, and separated by column chromatography to obtain 24.7 g (30% yield) of the compound represented by 4-a.

Step 2: Preparation of the compound represented by Formula 54

As shown in Scheme 24 below, a compound represented by Formula 54 was prepared.

[Scheme 24]

In a round bottom flask, the compound represented by 1-g obtained from Scheme 7 (13.2 g, 35 mmol) and the compound represented by 4-a obtained from Scheme 23 (27.5 g, 71 mmol), copper (6.8 g, 106 mmol) , Potassium carbonate (19.6 g, 142 mmol), 18-crown-6 (1.9 g, 7 mmol), and 132 ml of 1,2-dichlorobenzene were added, followed by refluxing for 72 hours. After the reaction was completed, it was filtered and 1,2-dichlorobenzene was concentrated. After cooling to room temperature, normal hexane was added to form a solid, filtered, recrystallized with 1,2-dichlorobenzene, and dried to obtain 7 g (yield 27.4%) of a compound represented by Chemical Formula 54.

MS [M] ⁺ 680

< Manufacturing example 5> Preparation of the compound represented by Chemical Formula 84

Step 1: Preparation of the compound represented by formula 5-a

As shown in Scheme 25 below, a compound represented by Formula 5-a was prepared.

[Scheme 25]

In a round bottom flask, 20.7 g (91.6 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine, 20.9 g (91.6 mmol) of benzothiophene-4-boronic acid and tetrakis (tri Phenylphosphine) palladium 2.1 g (1.8 mmol) and potassium carbonate 25.3 g (183 mmol) were added to a mixed solvent of 100 ml of tetrahydrofuran, 100 ml of toluene, and 40 ml of water, followed by stirring and refluxing for 12 hours.

After completion of the reaction, the reaction product was separated into layers, the organic layer was concentrated under reduced pressure, followed by column chromatography using methylene chloride and hexane as developing solvents, recrystallized with hexane, filtered, and dried.As a result, 22.1 g of the compound represented by Formula 5-a 65%).

Step 2: Preparation of the compound represented by Formula 84

As shown in Scheme 26 below, a compound represented by Chemical Formula 84 was prepared.

[Scheme 26]

Except for using the compound represented by 5-a prepared in Scheme 25 instead of the compound represented by 4-a used in Scheme 24, 10.5 g of the compound represented by Formula 84 (yield 26.5%) Got it.

MS [M] ⁺ 710

< Manufacturing example 6> Preparation of the compound represented by Chemical Formula 135

Step 1: Preparation of the compound represented by formula 6-a

As shown in Scheme 27 below, a compound represented by Formula 6-a was prepared.

[Scheme 27]

Except for using 2-bromo-4-iodoaniline instead of 2-bromo aniline in Scheme 6, it was carried out in the same manner as in Schemes 6,7,8, and 15 g of the compound represented by Formula 6-a (yield 35.5%) was obtained.

Step 2: Preparation of the compound represented by Formula 135

As shown in Scheme 28 below, a compound represented by Chemical Formula 135 was prepared.

[Scheme 28]

In a round-bottom flask, the compound represented by 6-a obtained from Scheme 27 (15.0 g, 21 mmol), 9-phenylcarbazole-3-boronic acid (7.7 g, 27 mmol), tetrakistriphenylphosphine palladium 0.5 g (0.5 mmol), potassium carbonate 5.7 g (41 mmol), water 30 ml, toluene 75 ml, and 1,4-dioxane 75 ml were added, followed by refluxing for 12 hours. After completion of the reaction, the reaction product was separated into layers, the organic layer was concentrated under reduced pressure, recrystallized with 1,2-dichlorobenzene, and dried to obtain 7 g (yield 31.0%) of the compound represented by Chemical Formula 135.

MS [M] ⁺ 845

< Manufacturing example 7> Preparation of the compound represented by Formula 136

Step 1: Preparation of the compound represented by 7-a

As shown in Scheme 29 below, a compound represented by 7-a was prepared.

[Scheme 29]

The compound represented by 7-a was carried out in the same manner as in Schemes 19, 20, 21 and 22, except that ethyl 2-amino-5-iodo benzoate was used instead of ethyl 2-amino benzoate used in Scheme 19. 21 g (yield 32.4%) was obtained.

Step 2: Preparation of the compound represented by Formula 136

As shown in Scheme 30 below, a compound represented by Chemical Formula 136 was prepared.

[Scheme 30]

Except that the compound represented by 7-a was used instead of the compound represented by 6-a used in Scheme 28, and 4-dibenzofuranylboronic acid was used instead of 9-phenylcarbazole-3-boronic acid. Then, by performing the same method, 7 g (yield 34.2%) of a compound represented by Chemical Formula 136 was obtained.

MS [M] ⁺ 854

< Manufacturing example 8> Preparation of the compound represented by Formula 139

As shown in Scheme 31 below, a compound represented by Chemical Formula 139 was prepared.

[Scheme 31]

Instead of the compound represented by 4-a used in Scheme 24, 7-a prepared in Scheme 29 was used, and the same method was performed except that carbazole was used instead of the compound represented by 1-g. The displayed compound 4 g (yield 35.6%) was obtained.

MS [M] ⁺ 853

Example

< Example 1 to 20> Organic light emitting device Produce

The ITO glass was patterned so that the light emitting area was 2 mm×2 mm and washed. After mounting the substrate in a vacuum chamber, the base pressure is 1×10 ^-6 torr, and then the organic material is placed on the ITO DNTPD (700 Å), NPD (300 Å), the compound prepared by the present invention + Ir (ppy) ₃ ( 10%) (300 Å), Alq ₃ (350 Å), LiF (5 Å), and Al (1,000 Å) were formed in this order, and the measurement was performed at 0.4 mA.

[DNTPD]

[NPD]

[Ir(ppy) ₃ ]

[Alq ₃ ]

< Comparative example 1>

The organic light emitting diode device for the comparative example was fabricated in the same manner, except that CBP was used instead of the compound prepared by the present invention as a host material in the device structure of the above example.

[CBP]

division Host Dopant Doping concentration% V CD /m ² CIEx CIEy T ₈₀ ( Hr ) Comparative Example 1 CBP Ir(ppy) ₃ 15 7.7 3800 0.294 0.622 71 Example 1 2 Ir(ppy) ₃ 15 4.1 5700 0.330 0.629 162 Example 2 3 Ir(ppy) ₃ 15 4.3 5500 0.328 0.627 145 Example 3 35 Ir(ppy) ₃ 15 4.5 4600 0.330 0.627 139 Example 4 54 Ir(ppy) ₃ 15 3.9 4500 0.327 0.624 115 Example 5 84 Ir(ppy) ₃ 15 3.9 4800 0.328 0.625 135 Example 6 135 Ir(ppy) ₃ 15 4.0 5000 0.327 0.624 102 Example 7 136 Ir(ppy) ₃ 15 4.2 4500 0.329 0.622 127 Example 8 139 Ir(ppy) ₃ 15 4.5 5200 0.330 0.623 115 Example 9 4 Ir(ppy) ₃ 15 4.0 4700 0.327 0.625 124 Example 10 5 Ir(ppy) ₃ 15 4.1 4900 0.331 0.627 120 Example 11 21 Ir(ppy) ₃ 15 4.8 5900 0.330 0.625 135 Example 12 39 Ir(ppy) ₃ 15 4.3 4900 0.329 0.627 136 Example 13 41 Ir(ppy) ₃ 15 4.6 5200 0.328 0.624 115 Example 14 43 Ir(ppy) ₃ 15 5.0 5300 0.330 0.627 124 Example 15 82 Ir(ppy) ₃ 15 3.9 5700 0.331 0.624 110 Example 16 106 Ir(ppy) ₃ 15 3.7 4800 0.329 0.622 121 Example 17 140 Ir(ppy) ₃ 15 3.9 5100 0.328 0.625 120 Example 18 144 Ir(ppy) ₃ 15 4.5 5500 0.329 0.625 135 Example 19 148 Ir(ppy) ₃ 15 4.7 4900 0.328 0.624 120 Example 20 149 Ir(ppy) ₃ 15 5.0 5300 0.331 0.629 106

As shown in Table 1, the organic electroluminescent device including the heterocyclic compound prepared according to Examples 1 to 20 of the present invention as a host material is a conventional phosphorescent host material CBP (Comparative Example 1) (7.7 V) Compared to that, the driving voltage (V) is as low as 3.7 to 5.0 V, and has excellent luminous efficiency (Cd/m2) and long life (T ₈₀ ), so it can be usefully used for display devices, display devices, and lighting.

10: substrate 20: anode
30: hole injection layer 40: hole transport layer
50: organic light emitting layer 60: electron transport layer
70: electron injection layer 80: cathode

Claims (8)

Heterocyclic compound represented by the following [Chemical Formula 1]:
[Formula 1]

In the above [Formula 1],
A ₁ to A ₄ are each independently C or -CH, and two adjacent two of A ₁ to A ₄ are each C, wherein two adjacent two are bonded to L to form a condensed ring,
Where L is

ego,
Y and Z are each independently a single bond or CR ₂ R ₃ or NR ₂ ,
Ar is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,
R ₁ to R ₃ are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms It is selected from groups (the R ₂ and R ₃ are bonded to each other to form a ring),
X ₁ to X ₁₆ are each independently hydrogen, deuterium, a halogen atom, a cyano group, an amino group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a substituted or unsubstituted It is selected from a heteroaryl group having 2 to 30 carbon atoms,
l, n and m are each independently an integer of 0 to 1. delete The method of claim 1,
Ar, R ₁ and R ₃ , X ₁ and X ₁₆ are each independently deuterium, a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, an aryl having 5 to 24 carbon atoms Group, a C2-C24 heteroaryl group, a C1-C20 alkoxy group, a C1-C20 alkylsilyl group, a C5-C24 arylsilyl group, a C1-C20 alkylamine group, and a C6-24C A heterocyclic compound, characterized in that further substituted with one or more substituents selected from the arylamine groups of, and wherein the substituents combine with each other to form a saturated or unsaturated ring. The method of claim 1,
[Formula 1] is a heterocyclic compound, characterized in that any one selected from the group consisting of compounds represented by the following [Formula 2] to [Formula 213]:

[Formula 2] [Formula 3] [Formula 4] [Formula 5]

[Formula 6] [Formula 7] [Formula 8] [Formula 9]

[Formula 10] [Formula 11] [Formula 12] [Formula 13]

[Formula 14] [Formula 15] [Formula 16] [Formula 17]

[Formula 18] [Formula 19] [Formula 20] [Formula 21]

[Formula 22] [Formula 23] [Formula 24] [Formula 25]

[Formula 26] [Formula 27] [Formula 28] [Formula 29]

[Formula 30] [Formula 31] [Formula 32] [Formula 33]

[Formula 34] [Formula 35] [Formula 36] [Formula 37]

[Formula 38] [Formula 39] [Formula 40] [Formula 41]

[Formula 42] [Formula 43] [Formula 44] [Formula 45]

[Chemical Formula 46] [Chemical Formula 47] [Chemical Formula 48] [Chemical Formula 49]

[Formula 50] [Formula 51] [Formula 52] [Formula 53]

[Formula 54] [Formula 55] [Formula 56] [Formula 57]

[Chemical Formula 58] [Chemical Formula 59] [Chemical Formula 60] [Chemical Formula 61]

[Formula 62] [Formula 63] [Formula 64] [Formula 65]

[Formula 66] [Formula 67] [Formula 68] [Formula 69]

[Formula 70] [Formula 71] [Formula 72] [Formula 73]

[Formula 74] [Formula 75] [Formula 76] [Formula 77]

[Chemical Formula 78] [Chemical Formula 79] [Chemical Formula 80] [Chemical Formula 81]

[Formula 82] [Formula 83] [Formula 84] [Formula 85]

[Formula 86] [Formula 87] [Formula 88] [Formula 89]

[Formula 90] [Formula 91] [Formula 92] [Formula 93]

[Formula 94] [Formula 95] [Formula 96] [Formula 97]

[Formula 98] [Formula 99] [Formula 100] [Formula 101]

[Formula 102] [Formula 103] [Formula 104] [Formula 105]

[Formula 106] [Formula 107] [Formula 108] [Formula 109]

[Formula 110] [Formula 111] [Formula 112] [Formula 113]

[Formula 114] [Formula 115] [Formula 116] [Formula 117]

[Chemical Formula 118] [Chemical Formula 119] [Chemical Formula 120] [Chemical Formula 121]

[Formula 122] [Formula 123] [Formula 124] [Formula 125]

[Formula 126] [Formula 127] [Formula 128] [Formula 129]

[Formula 130] [Formula 131] [Formula 132] [Formula 133]

[Formula 134] [Formula 135] [Formula 136] [Formula 137]

[Formula 138] [Formula 139] [Formula 140] [Formula 141]

[Formula 142] [Formula 143] [Formula 144] [Formula 145]

[Chemical Formula 146] [Chemical Formula 147] [Chemical Formula 148] [Chemical Formula 149]

[Formula 150] [Formula 151] [Formula 152] [Formula 153]

[Formula 154] [Formula 155] [Formula 156] [Formula 157]

[Formula 158] [Formula 159] [Formula 160] [Formula 161]

[Formula 162] [Formula 163] [Formula 164] [Formula 165]

[Formula 166] [Formula 167] [Formula 168] [Formula 169]

[Chemical Formula 170] [Chemical Formula 171] [Chemical Formula 172] [Chemical Formula 173]

[Formula 174] [Formula 175] [Formula 176] [Formula 177]

[Formula 178] [Formula 179] [Formula 180] [Formula 181]

[Formula 182] [Formula 183] [Formula 184] [Formula 185]

[Formula 186] [Formula 187] [Formula 188] [Formula 189]

[Formula 190] [Formula 191] [Formula 192] [Formula 193]

[Formula 194] [Formula 195] [Formula 196] [Formula 197]

[Formula 198] [Formula 199] [Formula 200] [Formula 201]

[Chemical Formula 202] [Chemical Formula 203] [Chemical Formula 204] [Chemical Formula 205]

[Formula 206] [Formula 207] [Formula 208] [Formula 209]

[Formula 210] [Formula 211] [Formula 212] [Formula 213] Anode; Cathode; And a layer including the heterocyclic compound represented by [Chemical Formula 1] according to claim 1, interposed between the anode and the cathode. The method of claim 5,
The heterocyclic compound is an organic electroluminescent device, characterized in that contained in the emission layer between the anode and the cathode. The method of claim 6,
An organic light-emitting device comprising at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer between the anode and the cathode. The method of claim 7,
At least one layer 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 is formed by a single molecule deposition method or a solution process.

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