KR102191022B1 - 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 including the same, wherein the heterocyclic compound is represented by the following [Chemical Formula 1], and the organic electroluminescent device including the same is a driving voltage, light emission The efficiency and life characteristics are very good.
[Formula 1]

Description

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

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

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.

An organic electroluminescent device using an organic light emitting phenomenon 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 for the organic electroluminescent device to fully exhibit the above-described excellent features, materials that form the organic material layer in the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials, are supported by stable and efficient materials. Although this should be preceded, the development of a stable and efficient organic material layer material for an organic light emitting device has not been made sufficiently. Therefore, the development of new materials continues to be required.

The problem to be solved by the present invention is to provide a novel heterocyclic compound and an organic electroluminescent device including the same and capable of low voltage driving and improved luminous efficiency.

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

[Formula 1]

A specific substituent of the above [Formula 1] will be described later.

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

Since the heterocyclic compound represented by [Chemical Formula 1] according to 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, The luminous efficiency can be improved.

1 is a schematic diagram of an organic electroluminescent device 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 emitting characteristics such as driving voltage and current efficiency of an organic light emitting device, and is characterized in that it is a heterocyclic compound represented by the following [Formula 1].

[Formula 1]

In the above [Formula 1],

Y may be any one selected from the group consisting of O, S, CR ₂ R ₃ , NR ₄ and SiR ₅ R ₆ .

Ar may be selected from the group consisting of 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, p is an integer of 1 to 3, and p is 2 or more Each of the plurality of Ars may be the same or different from each other.

L is a linking group, which is a single bond or a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, and a substituted or unsubstituted C2 to C60 group. Alkenylene group, substituted or unsubstituted C2-C60 alkynylene group, substituted or unsubstituted C3-C60 Selected from the group consisting of a cycloalkylene group, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms And n is an integer between 1 and 3, and when n is 2 or more, a plurality of L may be the same or different from each other.

X ₁ To X ₁₄ may be the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted carbon number 2 Heteroaryl group, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted An alkenyl group having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or Unsubstituted C5 to C30 cycloalkenyl group, substituted or unsubstituted C5 to C60 aryloxy group, substituted or unsubstituted C1 to C30 alkylthiooxy group, substituted or unsubstituted C5 to C30 It may be selected from the group consisting of an arylthioxy group, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, -SiR ₇ R ₈ R ₉ and -NR ₁₀ R ₁₁ .

In addition, the X ₁₁ to X ₁₄ may each be connected with a substituent adjacent to each other to form an alicyclic, aromatic monocyclic or polycyclic ring, and the formed alicyclic, aromatic monocyclic or polycyclic carbon atom is N, It may be substituted with one or more heteroatoms selected from S and O.

In addition, the R ₁ to R ₁₁ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted It may be selected from the group consisting of a heteroaryl group having 2 to 30 carbon atoms.

According to an embodiment of the present invention, the heterocyclic compound represented by [Chemical Formula 1] may be one of compounds represented by the following [Chemical Formula 2] to [Chemical Formula 9]:

[Chemical Formula 2] [Chemical Formula 3]

[Chemical Formula 4] [Chemical Formula 5]

[Formula 6] [Formula 7]

[Chemical Formula 8] [Chemical Formula 9]

In [Chemical Formula 2] to [Chemical Formula 9], Y, X ₁ To X ₁₄ , R ₁ to R ₁₁ , Ar and p are the same as defined in [Chemical Formula 1].

According to an embodiment of the present invention, the R ₁ to R ₁₁ , X ₁₁ to X ₁₄ , L, Ar are each independently a deuterium atom, a cyano group, a halogen atom, a hydroxy group, a nitro group, an alkyl group having 1 to 40 carbon atoms, Alkoxy group having 1 to 40 carbon atoms, alkylamino group having 1 to 40 carbon atoms, arylamino group having 6 to 40 carbon atoms, heteroarylamino group having 3 to 40 carbon atoms, alkylsilyl group having 1 to 40 carbon atoms, arylsilyl group having 6 to 40 carbon atoms , Aryl group having 6 to 40 carbon atoms, aryloxy group having 3 to 40 carbon atoms, heteroaryl group having 3 to 40 carbon atoms, germanium group, may be further substituted with one or more substituents selected from the group consisting of phosphorus and boron, The substituents may be bonded to each other with adjacent substituents to form a saturated or unsaturated ring, or may be attached or fused together in a pendant manner.

Specific examples of the alkyl group as a substituent used in the present invention include methyl group, ethyl group, propyl 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, and the like, and at least one hydrogen atom in 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 " Alkylsilyl group"), a substituted or unsubstituted amino group (-NH ₂ , -NH(R), -N(R')(R"), wherein R, R'and R" are each independently a C 1 It is an alkyl group of to 24 (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 C1-C24 alkyl group, a C1-C24 halogenated alkyl group Alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 5 to 24 carbon atoms, arylalkyl group having 6 to 24 carbon atoms, heteroaryl group having 3 to 24 carbon atoms or carbon number It may be substituted with 3 to 24 heteroarylalkyl groups.

Specific examples of the alkoxy group as a substituent used in the compound of the present invention include methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group, hexyloxy group, etc. And the same substituents as in the case of the above 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 aryl group as a substituent used in the compound of 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, In addition, when the aryl group has a substituent, it may be fused with neighboring substituents to further form a 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, pyre And aromatic groups such as nil group, indenyl, fluorenyl group, tetrahydronaphthyl group, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, and the like, but are not limited thereto.

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.

A heteroaryl group, which is a substituent used in the compound of the present invention, particularly, when Ar is a heteroaryl group, it may be any one of 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 C 5 to C 50 aryl group and a substituted or unsubstituted C 2 to C 50 heteroaryl group having O, N or S as a hetero atom, and each of [Structural Formula 1] to [Structural Formula 6] in the above R ₃₁ to R ₄₄ One of them may form a single bond by bonding with nitrogen in [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 the [Structural Formula 7], X is the same as X ₁ to X ₁₄ , m is an integer of 1 to 11, and when m is 2 or more, a plurality of Xs are the same or different from each other, and any one of the at least one X May form a single bond by bonding with nitrogen in the [Chemical Formula 1].

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, fluorenyloxy, Indenyloxy, etc., 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, silyl, diphenylvinylsilyl, methylcyclobutylsilyl And dimethylfurylsilyl.

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.

In addition, in the present invention, the'substituted' in the'substituted or unsubstituted' is deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, 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, heteroaryl group having 2 to 24 carbon atoms or carbon number 2 to 24 heteroarylalkyl group, C 1 to C 24 alkoxy group, C 1 to C 24 alkylamino group, C 1 to C 24 arylamino group, C 1 to C 24 hetero arylamino group, C 1 to C 24 alkylsilyl group, It means substituted with one or more substituents selected from the group consisting of an arylsilyl group having 1 to 24 carbon atoms, an aryloxy group having 1 to 24 carbon atoms, germanium, phosphorus and boron.

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", "substituted or unsubstituted aryl group having 5 to 50 carbon atoms", etc. considers the portion where the substituent is substituted It does not mean the total number of carbon atoms constituting the alkyl moiety or aryl moiety when viewed as unsubstituted. For example, a phenyl group in which a butyl group is substituted at the para position means that it corresponds to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

According to a preferred embodiment of the present invention, the heterocyclic compound represented by [Chemical Formula 1] according to the present invention may be any one compound selected from the group consisting of compounds represented by the following [Chemical Formula 10] to [Chemical Formula 192]. .

[Formula 10] [Formula 11]

[Formula 12] [Formula 13]

[Formula 14] [Formula 15]

[Formula 16] [Formula 17]

[Chemical Formula 18] [Chemical Formula 19]

[Formula 20] [Formula 21]

[Formula 22] [Formula 23]

[Formula 24] [Formula 25]

[Formula 26] [Formula 27]

[Formula 28] [Formula 29]

[Chemical Formula 30] [Chemical Formula 31]

[Formula 32] [Formula 33]

[Formula 34] [Formula 35]

[Chemical Formula 36] [Chemical Formula 37]

[Chemical Formula 38] [Chemical 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]

[Chemical Formula 54] [Chemical Formula 55]

[Chemical Formula 56] [Chemical Formula 57]

[Chemical Formula 58] [Chemical Formula 59]

[Chemical Formula 60] [Chemical Formula 61]

[Formula 62] [Formula 63]

[Formula 64] [Formula 65]

[Chemical Formula 66] [Chemical Formula 67]

[Chemical Formula 68] [Chemical Formula 69]

[Formula 70] [Formula 71]

[Chemical Formula 72] [Chemical Formula 73]

[Formula 74] [Formula 75]

[Chemical Formula 76] [Chemical 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]

[Chemical Formula 88] [Chemical Formula 89]

[Formula 90] [Formula 91]

[Formula 92] [Formula 93]

[Formula 94] [Formula 95]

[Chemical Formula 96] [Chemical Formula 97]

[Chemical Formula 98] [Chemical Formula 99]

[Chemical Formula 100] [Chemical Formula 101]

[Formula 102] [Formula 103]

[Chemical Formula 104] [Chemical Formula 105]

[Formula 106] [Formula 107]

[Chemical Formula 108] [Chemical Formula 109]

[Chemical Formula 110] [Chemical Formula 111]

[Chemical Formula 112] [Chemical Formula 113]

[Chemical Formula 114] [Chemical Formula 115]

[Chemical Formula 116] [Chemical Formula 117]

[Chemical Formula 118] [Chemical Formula 119]

[Chemical Formula 120] [Chemical Formula 121]

[Formula 122] [Formula 123]

[Chemical Formula 124] [Chemical Formula 125]

[Chemical Formula 126] [Chemical Formula 127]

[Chemical Formula 128] [Chemical Formula 129]

[Chemical Formula 130] [Chemical Formula 131]

[Chemical Formula 132] [Chemical Formula 133]

[Formula 134] [Formula 135]

[Chemical Formula 136] [Chemical Formula 137]

[Chemical Formula 138] [Chemical Formula 139]

[Chemical Formula 140] [Chemical Formula 141]

[Chemical Formula 142] [Chemical Formula 143]

[Formula 144] [Formula 145]

[Chemical Formula 146] [Chemical Formula 147]

[Formula 148] [Formula 149]

[Chemical Formula 150] [Chemical Formula 151]

[Formula 152] [Formula 153]

[Chemical Formula 154] [Chemical 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]

[Chemical Formula 168] [Chemical Formula 169]

[Chemical Formula 170] [Chemical Formula 171]

[Formula 172] [Formula 173]

[Formula 174] [Formula 175]

[Formula 176] [Formula 177]

[Formula 178] [Formula 179]

[Chemical Formula 180] [Chemical Formula 181]

[Chemical Formula 182] [Chemical Formula 183]

[Chemical Formula 184] [Chemical Formula 185]

[Formula 186] [Formula 187]

[Formula 188] [Formula 189]

[Chemical Formula 190] [Chemical Formula 191]

[Formula 192]

In addition, the present invention includes a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer is represented by the above [Formula 1] It may contain one or more cyclic compounds.

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

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

In addition, in the present invention, a known electron transport material may be used as the material for the electron transport layer, which has a function of stably transporting electrons injected from an electron injection electrode (Cathode). Examples of known electron transport materials include quinoline derivatives, in particular tris(8-quinolinorate)aluminum (Alq3), TAZ, Balq, beryllium bis(benzoquinolin-10-noate) (beryllium bis(benzoquinolin-10-). olate: Bebq2), ADN, [Compound 201], [Compound 202], and oxadiazole derivatives such as PBD, BMD, BND, and the like may be used.

TAZ BAlq

[Compound 201] [Compound 202] BCP

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

[Formula C]

In [Chemical Formula C],

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

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

OA is a monovalent ligand capable of a single bond or coordination bond with M, wherein O is oxygen, and A is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms Any one selected from an alkenyl group and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom.

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

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

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

[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 [Structural Formula C1] to [Structural Formula C39],

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

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

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

1 is a cross-sectional view showing the structure of an organic light emitting 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.

The hole injection layer material is not particularly limited as long as it is commonly used in the art, and may be used, for example, 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine] , NPD[N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD[N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'- biphenyl-4,4'-diamine], DNTPD[N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine ], etc. can be used.

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

Subsequently, 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.

As a material used for the hole blocking layer, any one selected from BAlq, BCP, Bphen, TPBI, NTAZ, BeBq ₂ , OXD-7, Liq, and [Formula 101] to [Formula 107] may be used, but limited thereto It does not become.

BAlq BCP Bphen

TPBI NTAZ BeBq ₂

OXD-7 Liq

Formula 101 Formula 102 Formula 103

Formula 104 Formula 105 Formula 106

Chemical Formula 107

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, the emission layer may be formed of a host and a dopant, and according to a specific example of the present invention, the thickness of the emission layer is preferably 50 to 2,000 Å.

In this case, the dopant used in the light emitting layer may be one or more compounds selected from compounds represented by the following [General Formula A-1] to [General Formula J-1].

[General Formula A-1]

In the above [general formula A-1],

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.

In addition, the L ₁ , L ₂ and L ₃ may be the same as or different from each other as a ligand, and each independently may be any one selected from the following [Structural Formula D], and "*" in the following Structural Formula D is coordinated to the metal ion M Express the site.

[Structural Formula D]

In the [Structural Formula D],

R is different from each other or the same, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted carbon number 5 to 50 heteroaryl group, substituted or unsubstituted C 1 to C 30 alkoxy group, substituted or unsubstituted C 3 to C 30 cycloalkyl group, substituted or unsubstituted C 2 to C 30 alkenyl group, substituted or unsubstituted A substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, 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 It may be any one selected from, and wherein R is each independently 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 may be further substituted with one or more substituents selected from, and the R is connected to each of the adjacent substituents by alkylene or alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring. I can.

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

According to an embodiment of the present invention, the dopant represented by [General Formula A-1] may be any one selected from the following compounds.

[General Formula B-1]

In the above [general formula B-1],

M ^A1 represents the same metal ion as defined in [General Formula A-1], and Y ^A11 , Y ^A14 , Y ^A15 and Y ^A18 Each independently represents a carbon atom or a nitrogen atom, Y ^A12 , Y ^A13 , Y ^A16 and Y ^A17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom, and a sulfur atom, L ^A11 , L ^A12 , L ^A13 , L ^A14 each represent a linking group such as L ₁ , L ₂ and L ₃ defined in [General Formula A-1], and Q ^A11 and Q ^A12 represent an atom bonded to M ^A1 It shows the partial structure to contain.

According to an embodiment of the present invention, the compound represented by [General Formula B-1] may be any one selected from the following compounds.

[General Formula C-1]

In the above [general formula C-1],

M ^B1 represents the same metal ion as defined in [General Formula A-1], Y ^B11 , Y ^B14 , Y ^B15 and Y ^B18 each independently represent a carbon atom or a nitrogen atom, and 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, and a sulfur atom, L ^B11 , L ^B12 , L ^B13 , L ^B14 represent a linking group, Q ^B11 , Q ^B12 represents a partial structure containing an atom bonded to M ^B1 .

According to an embodiment of the present invention, the compound represented by [General Formula C-1] may be any one selected from the following compounds.

[General Formula D-1]

In the above [general formula D-1],

M ^C1 represents the same metal ion as defined in [General Formula A-1], and R ^C11 and R ^C12 each independently represent a hydrogen atom, a substituent that is connected to each other to form a 5-membered ring, and a substituent that is not connected to each other. , R ^C11 and R ^C12 each independently represent a hydrogen atom, a substituent that is connected to each other to form a 5-membered ring, and a substituent that is not connected to each other, and R ^C13 and R ^C14 are each independently a hydrogen atom, each of which is a 5-membered ring Represents a substituent that forms a substituent, a substituent that is not connected to each other, G ^C11 , G ^C12 each independently represents a nitrogen atom, a substituted or unsubstituted carbon atom, L ^C11 , L ^C12 represents a linking group, Q ^C11 , Q ^C12 Represents a partial structure containing an atom bonded to M ^C1 .

According to an embodiment of the present invention, the compound represented by [General Formula D-1] may be any one selected from the following compounds.

[General Formula E-1]

In the above [general formula E-1],

M ^D1 represents the same metal ion as defined in [General Formula A-1], and G ^D11 and G ^D12 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, and J ^D11 , J ^D12 , J ^D13 And J ^D14 each independently represent an atomic group required to form a 5-membered ring, and L ^D11 and L ^D12 represent a linking group.

According to an embodiment of the present invention, the compound represented by [General Formula E-1] may be any one selected from the following compounds.

[General Formula F-1]

In the above [general formula F-1],

M ^E1 represents the same metal ion as defined in [General Formula A-1], and J ^E11 and J ^E12 each independently represent an atomic group required to form a 5-membered ring, G ^E11 , G ^E12 , G ^E13 and G ^E14 each independently represents 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.

According to an embodiment of the present invention, the compound represented by [General Formula F-1] may be any one selected from the following compounds.

[General Formula G-1]

In the above [general formula G-1],

M ^F1 represents the same metal ion as defined in [General Formula A-1], L ^F11 , L ^F12 and L ^F13 represent a linking group, R ^F11 , R ^F12 , R ^F13 and R ^F14 represent a substituent, and R ^F11 and R ^F12 , R ^F12 And R ^F13 , R ^F13 and R ^F14 may be linked to each other to form a ring, wherein the ring formed by R ^F1 and R ^F12 , R ^F13 and R ^F14 is a 5-membered ring. In addition, Q ^F11 and Q ^F12 represent a partial structure containing an atom bonded to M ^F1 .

According to an embodiment of the present invention, the compound represented by [General Formula G-1] may be any one selected from the following compounds.

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

In the above [General Formula H-1],

R ¹¹ and R ¹² are an alkyl group, an aryl group, or a heteroaryl group, and may form a fused ring with a substituent adjacent to each other, and q11 and q12 are integers of 0 to 4, preferably 0 to 2. Further, when q11 and q12 are 2 to 4, a plurality of R11 and R12 may be the same or different, respectively.

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

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

In addition, it is preferable that n ¹ and m ¹ make the metal complex represented by the above [General Formula H-1] a neutral complex.

In the above [General Formula H-2],

R ²¹ , R ²² , n ² , m ² , q ²² , L ² are the same as R ¹¹ , R ¹² , n ¹ , m ¹ , q ¹² and L ¹ , respectively, and q ²¹ is an integer of 0 to 2 , 0 is preferred.

In the above [General Formula H-3],

R ³¹ , n ³ , m ³ , L ³ are the same as R ¹¹ , n ¹ , m ¹ , and L ¹ , respectively, and q ³¹ represents an integer of 0 to 8, preferably 0 to 2, and more than 0 desirable.

According to an embodiment of the present invention, the compound represented by [General Formula H-1] to [General Formula H-3] may be any one selected from the following compounds.

[General Formula I-1]

In the above [general formula I-1],

Ring A, Ring B, Ring C, and Ring D represent a nitrogen-containing heterocycle in which any two of the rings A to D may have a substituent, and the other two rings are an aryl ring or heteroaryl which may have a substituent. Represents a ring, and can form a condensed ring with ring A and ring B, ring A and ring C, and/or ring B and ring D.

X ¹ , X ² , X ³ and X ⁴ represent a nitrogen atom in which two of them are coordinated to a platinum atom, and the other two represent a carbon atom or a nitrogen atom.

Q ¹ , Q ² and Q ³ each independently represent a divalent atom (term) or a bond, but Q ¹ , Q ² and Q ³ do not represent a bond at the same time. Z ¹ , Z ² , Z ³ and Z ⁴ are any two representing a coordination bond, and the other two represent a covalent bond, an oxygen atom or a sulfur atom.

According to an embodiment of the present invention, the compound represented by [General Formula I-1] may be any one selected from the following compounds.

[General Formula J-1]

In the above [general formula J-1],

M represents the same metal ion as defined in [General Formula A-1], Ar1 represents a substituted or unsubstituted ring structure, and two azomethine bonds (-C=N-) bonded to the M In ), the nitrogen atom (N) is each bonded to the M, and as a whole, forms a tridentate ligand bonded to the M at three loci.

In addition, in Ar1, C represents a carbon atom constituting the ring structure represented by Ar1. In addition, R1 and R2 may be the same as or different from each other, and each represents a substituted or unsubstituted alkyl group or aryl group, and L represents a monodentate ligand.

The M is preferably Pt, and Ar1 is preferably selected from a 5-membered ring, a 6-membered ring, and a condensed ring group thereof.

According to an embodiment of the present invention, the compound represented by [General Formula J-1] may be any one selected from the following compounds.

In addition, the emission layer may further include various hosts and various dopant materials in addition to the dopant and host.

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

In addition, the organic electroluminescent device according to the present invention may be used in a device selected from a flat panel display device, a flexible display device, a monochrome or white flat lighting device, and a single color or white flexible lighting device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for explaining the present invention in more detail, and it will be apparent to those of ordinary skill in the art that the scope of the present invention is not limited thereto.

< Example >

<Synthesis Example 1> Synthesis of a compound represented by [Chemical Formula 10]

(1) Synthesis of a compound represented by [Formula 1-a]

A compound represented by [Chemical Formula 1-a] was synthesized by the following [Scheme 1].

[Scheme 1]

[Formula 1-a]

6-bromoindole 50.0 g (255.0 mmol), iodobenzene 10.4 g (510.0 mmol), copper powder 32.4 g (510.0 mmol), 18-crown-6 13.5 g (51.0 mmol), potassium carbonate 105.7 g (765.0 mmol) ) In order, 500 ml of 1,2-dichlorobenzene was added, and then refluxed and stirred at 180° C. for 1 day. When the reaction was completed, the solution was concentrated under reduced pressure after high-temperature filtering, and the organic layer solution was subjected to column chromatography with hexane alone to obtain 57.6 g of a compound represented by [Chemical Formula 1-a]. (83% yield)

(2) Synthesis of a compound represented by [Formula 1-b]

A compound represented by [Chemical Formula 1-b] was synthesized by the following [Scheme 2].

[Scheme 2]

[Formula 1-a] [Formula 1-b]

After dissolving 57.6 g (211.6 mmol) of the compound represented by [Chemical Formula 1-a] obtained from [Scheme 1] in 600 ml of tetrahydrofuran under a stream of nitrogen, while stirring at -78°C, 159 ml of 1.6 M normal-butyllithium ( 253.9 mmol) was slowly added dropwise, and when the dropwise addition was completed, the mixture was stirred for 1 hour while maintaining -78°C. After that, 26.4 g (253.9 mmol) of trimethylborate was slowly added dropwise, and then heated to room temperature and stirred for 2 hours. Upon completion of the reaction, 300 ml of a 2 M aqueous hydrochloric acid solution was added dropwise at room temperature, followed by stirring for 30 minutes. Thereafter, extraction was performed with ethyl acetate and water, the organic layer was concentrated under reduced pressure, and recrystallized from methylene chloride and hexane to obtain 28.6 g of a compound represented by [Formula 1-b]. (Yield 57%)

(3) Synthesis of a compound represented by [Formula 1-c]

A compound represented by [Chemical Formula 1-c] was synthesized by the following [Scheme 3].

[Scheme 3]

[Formula 1-c]

2,4,6-trichloro-1,3,5-triazine 40.0 g (216.9 mmol), phenylboronic acid 63.5 g (520.6 mmol), tetrakis (triphenylphosphine) palladium 5.0 g (4.4 mmol), Potassium carbonate 72.0 g (520.6 mmol), 200 ml of 1,4-dioxane, 200 ml of toluene, and 80 ml of distilled water were added and stirred at 100° C. for 6 hours. When the reaction is completed, extraction is performed using ethyl acetate and distilled water. The organic layer was concentrated under reduced pressure and recrystallized from methylene chloride and acetone to obtain 34.8 g of a compound represented by [Chemical Formula 1-c]. (Yield 60%)

(4) Synthesis of a compound represented by [Formula 1-d]

A compound represented by [Chemical Formula 1-d] was synthesized by the following [Scheme 4].

[Scheme 4]

[Formula 1-d]

Carbazole 150.0 g (762.6 mmol) was dissolved in 1.0 L of dimethylformamide and then stirred at 0 °C. Thereafter, 135.7 g (762.6 mmol) of N-bromosuccinimide was dissolved in 0.5 L of dimethylformamide and slowly added dropwise for 1 hour while maintaining 0°C. When the dropwise addition is complete, the mixture is raised to room temperature and stirred for 12 hours. When the reaction was completed, distilled water was added dropwise at room temperature, and when brown crystals were formed, the crystals were filtered and recrystallized with toluene and methanol to obtain 110.0 g of a compound represented by [Chemical Formula 1-d]. (Yield 58%)

(5) Synthesis of a compound represented by [Formula 1-e]

A compound represented by [Chemical Formula 1-e] was synthesized by the following [Scheme 5].

[Scheme 5]

[Formula 1-d] [Formula 1-c] [Formula 1-e]

Compound 10.0 g (40.6 mmol) of the compound represented by [Chemical Formula 1-d] obtained from [Scheme 4] and 2.0 g (48.8 mmol) of 60% sodium hydride were added to 150 ml of dimethylformamide and stirred at room temperature for 30 minutes. . Then, 13.1 g (48.8 mmol) of chlorodiphenyltriazine was dissolved in 100 ml of dimethylformamide, slowly added dropwise, and stirred for 1 hour. When the reaction was completed, 10 ml of distilled water was added, filtered, and recrystallized to obtain 16.3 g of a compound represented by [Chemical Formula 1-e]. (Yield 85%)

(6) Synthesis of the compound represented by [Formula 10]

A compound represented by [Chemical Formula 10] was synthesized by the following [Scheme 6].

[Scheme 6]

[Formula 1-b] [Formula 1-e] [Formula 10]

9.7 g (41.0 mmol) of the compound represented by [Chemical Formula 1-b] obtained from [Scheme 2], 16.3 g (34.2 mmol) of the compound represented by [Chemical Formula 1-e] obtained from [Scheme 5], tetrakis (Triphenylphosphine) Palladium 790 mg (0.7 mmol), potassium carbonate 9.6 g (68.4 mmol), 1,4-dioxane 80 ml, toluene 80 ml, distilled water 30 ml, and stirred at 100° C. for 12 hours. When the reaction is completed, extraction is performed using ethyl acetate and distilled water. The organic layer was concentrated under reduced pressure and recrystallized from methylene chloride and acetone to obtain 10.7 g of a compound represented by [Chemical Formula 10]. (Yield 53%)

MS [M] ⁺ 590

¹³ C NMR (75 MHz, CDCl ₃ ) δ:

103 104.8 109.5 109.9 111.6 116.8 118.9 119.3 119.4 119.8 121.3 121.4 125.5 126.6 127.5 128.3 129.2 129.3 131.1 133 133.1 134.7 138.7 141.6 143.7 144.4 145.9 172.1 178.8 [41C]

<Synthesis Example 2> Synthesis of a compound represented by [Chemical Formula 92]

(1) Synthesis of a compound represented by [Formula 2-a]

A compound represented by [Chemical Formula 2-a] was synthesized by the following [Scheme 7].

[Scheme 7]

[Formula 2-a]

In place of (3) 2,4,6-trichloro-1,3,5-triazine in Synthesis Example 1, 2,4,6-trichloropyrimidine was added and the same as in Synthesis Example 1 (3) Synthesized by the method to obtain a compound represented by [Chemical Formula 2-a]. (Yield 50%)

(2) Synthesis of a compound represented by [Formula 2-b]

A compound represented by [Chemical Formula 2-b] was synthesized by the following [Scheme 8].

[Scheme 8]

[Formula 2-a] [Formula 2-b]

Compound 20.0 g (75.0 mmol) represented by [Formula 2-a] obtained from [Scheme 7], 4-bromophenylboronic acid 18.1 g (90.0 mmol), tetrakis (triphenylphosphine) palladium 1.7 g (1.5 mmol), potassium carbonate 20.7 g (150.0 mmol), 1,4-dioxane 100 ml, toluene 100 ml, distilled water 50 ml, and stirred at 100° C. for 12 hours. When the reaction is completed, extraction is performed using ethyl acetate and distilled water. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from methylene chloride and acetone to obtain 22.4 g of a compound represented by [Chemical Formula 2-b]. (Yield 77%)

(3) Synthesis of a compound represented by [Formula 2-c]

A compound represented by [Chemical Formula 2-c] was synthesized by the following [Scheme 9].

[Scheme 9]

[Formula 2-b] [Formula 2-c]

After dissolving 22.4 g (57.8 mmol) of the compound represented by [Chemical Formula 2-b] obtained from [Scheme 8] in 230 ml of tetrahydrofuran under a stream of nitrogen, and stirring at -78° C., 44 ml of 1.6 M normal-butyllithium ( 69.4 mmol) was slowly added dropwise, and when the dropwise addition was completed, the mixture was stirred for 1 hour while maintaining -78°C. After that, 17.6 g (69.4 mmol) of iodine was slowly added dropwise, and then heated to room temperature and stirred for 1 hour. Upon completion of the reaction, 230 ml of an aqueous sodium thiosulfate solution was added dropwise and stirred for 30 minutes. Thereafter, extraction was performed with ethyl acetate and water, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 22.1 g of a compound represented by [Chemical Formula 2-c]. (Yield 88%)

(4) Synthesis of a compound represented by [Formula 2-d]

A compound represented by [Chemical Formula 2-d] was synthesized by the following [Scheme 10].

[Scheme 10]

[Formula 2-c] [Formula 2-d]

Compound 22.1g (50.9 mmol) represented by [Chemical Formula 2-c] obtained from [Scheme 9], 12.5 g (50.9 mmol) compound represented by [Chemical Formula 1-d] obtained from [Scheme 4], copper powder 6.5 g (101.8 mmol), 18-crown-6 2.7 g (10.2 mmol), potassium carbonate 21.1 g (152.7 mmol) were added in that order, 1,2-dichlorobenzene 220 ml was added, and then at 180° C. for 12 hours Reflux and stir. When the reaction was completed, the solution was recrystallized from hexane at low temperature after high-temperature filtering to obtain 12.1 g of a compound represented by [Chemical Formula 2-d]. (Yield 43%)

(4) Synthesis of the compound represented by [Chemical Formula 92]

A compound represented by [Chemical Formula 92] was synthesized by the following [Scheme 11].

[Scheme 11]

[Formula 2-d] [Formula 92]

Compound 12.1 g (21.9 mmol) represented by [Formula 2-d] obtained from [Scheme 10], 6.2 g (26.3 mmol) compound represented by [Formula 1-b] obtained from [Scheme 2], tetrakis ( Triphenylphosphine) palladium 506 mg (0.4 mmol), potassium carbonate 6.1 g (43.8 mmol), 1,4-dioxane 60 ml, toluene 60 ml, distilled water 25 ml, and stirred at 100° C. for 12 hours. When the reaction was completed, the organic layer was concentrated under reduced pressure after high-temperature filtering, and recrystallized from methylene chloride and acetone to obtain 6.8 g of a compound represented by [Chemical Formula 92]. (Yield 47%)

MS [M] ⁺ 665

¹³ C NMR (75 MHz, CDCl ₃ ) δ:

104.8 105.4 108.8 109.5 109.9 111.6 114.1 116.8 118.9 119.3 119.4 119.8 121.3 121.4 125.5 126.6 127.5 128.1 128.3 128.7 129.2 129.3 131.5 134 135.5 135.8 136.8 138.7 141.6 143.7 145.4 145.9 155 164.6 [48C]

<Synthesis Example 3> Synthesis of a compound represented by [Chemical Formula 109]

(1) Synthesis of a compound represented by [Chemical Formula 3-a]

A compound represented by [Chemical Formula 3-a] was synthesized by the following [Scheme 12].

[Scheme 12]

[Formula 3-a]

6-bromoindole 20.0 g (102.0 mmol), 60% sodium hydride 4.9 g (122.4 mmol) was added to 200 ml of dimethylformamide and stirred at room temperature for 30 minutes. Thereafter, 32.8 g (122.4 mmol) of chlorodiphenyltriazine was dissolved in 150 ml of dimethylformamide, slowly added dropwise, and stirred for 1 hour. When the reaction was completed, 200 ml of distilled water was added, filtered, and recrystallized to obtain 37.0 g of a compound represented by [Chemical Formula 3-a]. (Yield 85%)

(2) Synthesis of a compound represented by [Chemical Formula 3-b]

A compound represented by [Chemical Formula 3-b] was synthesized by the following [Scheme 13].

[Scheme 13]

[Formula 3-b]

2-bromodibenzofuran 30.0 g (121.4 mmol), 3-bromophenylboronic acid 29.3 g (145.7 mmol), tetrakis (triphenylphosphine) palladium 2.8 g (2.4 mmol), potassium carbonate 33.6 g (243.9 mmol), 150 ml of 1,4-dioxane, 150 ml of toluene, and 60 ml of distilled water were added and stirred at 100° C. for 12 hours. When the reaction is completed, extraction is performed using ethyl acetate and distilled water. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from methylene chloride and acetone to obtain 24.3 g of a compound represented by [Chemical Formula 3-b]. (Yield 62%)

(3) Synthesis of a compound represented by [Formula 3-c]

A compound represented by [Chemical Formula 3-c] was synthesized by the following [Scheme 14].

[Scheme 14]

[Formula 3-b] [Formula 3-c]

After dissolving 24.3 g (75.3 mmol) of the compound represented by [Chemical Formula 3-b] obtained from [Scheme 13] in 240 ml of tetrahydrofuran under a stream of nitrogen, while stirring at -78 °C, 56.5 ml of 1.6M normal-butyllithium ( 90.4 mmol) was slowly added dropwise, and when the dropwise addition was completed, the mixture was stirred for 1 hour while maintaining -78°C. After that, 22.9 g (90.4 mmol) of iodine is slowly added dropwise, and then heated to room temperature and stirred for 1 hour. Upon completion of the reaction, 240 ml of sodium thiosulfate aqueous solution was added dropwise, followed by stirring for 30 minutes. Thereafter, extraction was performed with ethyl acetate and water, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 22.6 g of a compound represented by [Chemical Formula 3-c]. (Yield 81%)

(4) Synthesis of a compound represented by [Chemical Formula 3-d]

A compound represented by [Chemical Formula 3-d] was synthesized by the following [Scheme 15].

[Scheme 15]

[Formula 3-c] [Formula 3-d]

Compound 22.6g (60.1 mmol) represented by [Chemical Formula 3-c] obtained from [Scheme 14], 14.8 g (60.1 mmol) compound represented by [Chemical Formula 1-d] obtained from [Scheme 4], copper powder 7.6 g (120.2 mmol), 18-crown-6 3.2 g (12.0 mmol), potassium carbonate 24.9 g (180.3 mmol) were sequentially added, 1,2-dichlorobenzene 220 ml was added, and then at 180° C. for 12 hours Reflux and stir. When the reaction was completed, the solution was recrystallized from hexane at low temperature after high-temperature filtering to obtain 14.4 g of a compound represented by [Chemical Formula 3-d]. (Yield 49%)

(5) Synthesis of a compound represented by [Formula 3-e]

A compound represented by [Chemical Formula 3-e] was synthesized by the following [Scheme 16].

[Scheme 16]

[Formula 3-d] [Formula 3-e]

After dissolving 14.4 g (29.5 mmol) of the compound represented by [Chemical Formula 3-d] obtained from [Scheme 15] in 140 ml of tetrahydrofuran under a stream of nitrogen, while stirring at -78° C., 22 ml of 1.6 M normal-butyllithium ( 35.4 mmol) was slowly added dropwise, and when the dropwise addition was completed, the mixture was stirred for 1 hour while maintaining -78°C. After that, 3.7 g (35.4 mmol) of trimethylborate was slowly added dropwise, and then raised to room temperature and stirred for 3 hours. Upon completion of the reaction, 70 ml of a 2 M aqueous hydrochloric acid solution was added dropwise at room temperature, followed by stirring for 30 minutes. Thereafter, extraction was performed with ethyl acetate and water, the organic layer was concentrated under reduced pressure, and recrystallized in methylene chloride and hexane to obtain 9.0 g of a compound represented by [Chemical Formula 3-e]. (Yield 67%)

(6) Synthesis of a compound represented by [Chemical Formula 109]

A compound represented by [Chemical Formula 109] was synthesized by the following [Scheme 17].

[Scheme 17]

[Formula 3-e] [Formula 109]

Compound 9.0 g (19.9 mmol) represented by [Chemical Formula 3-e] obtained from [Scheme 16], 7.1 g (16.6 mmol) compound represented by [Chemical Formula 3-a] obtained from [Scheme 12], tetrakis (Triphenylphosphine) palladium 383 mg (0.3 mmol), potassium carbonate 4.6 g (33.2 mmol), 1,4-dioxane 45 ml, toluene 45 ml, distilled water 18 ml, and stirred at 100° C. for 12 hours. When the reaction is completed, extraction is performed using methylene chloride and distilled water. The organic layer was concentrated under reduced pressure and recrystallized from methylene chloride and acetone to obtain 7.2 g of a compound represented by [Chemical Formula 109]. (Yield 48%)

MS [M] ⁺ 756

¹³ C NMR (75 MHz, CDCl ₃ ) δ:

102.4 105.4 106.4 109.5 109.7 111.5 111.6 112 116.8 118.9 119.1 119.3 119.4 119.8 120.2 120.9 121.4 122.8 123.3 124.7 125.9 126.6 127.5 129.2 129.8 131.1 134 134.7 135.5 136.4 137.1 141.6 142.4 143.7 144.9 145.4 146 160.7 172.1 178.8 [53C]

<Synthesis Example 4> Synthesis of a compound represented by [Chemical Formula 110]

(1) Synthesis of a compound represented by [Formula 4-a]

A compound represented by [Chemical Formula 4-a] was synthesized by the following [Scheme 18].

[Scheme 18]

[Formula 4-a]

Compound 20.0 g (81.3 mmol) represented by [Chemical Formula 1-d] obtained from [Scheme 4], 2-iodobenzene 33.2 g (162.5 mmol), copper powder 10.3 g (162.5 mmol), 18-crown-6 4.3 g (16.3 mmol) and potassium carbonate 33.7 g (243.9 mmol) were added in that order, and 1,2-dichlorobenzene 200 ml was added, followed by refluxing and stirring at 180° C. for 1 day. When the reaction was completed, the solution was concentrated under reduced pressure after high-temperature filtering, and the organic layer solution was subjected to column chromatography using hexane alone to obtain 21.0 g of a compound represented by [Chemical Formula 4-a]. (Yield 88%)

(2) Synthesis of a compound represented by [Formula 4-b]

A compound represented by [Chemical Formula 4-b] was synthesized by the following [Scheme 19].

[Scheme 19]

[Formula 4-a] [Formula 4-b]

21.0 g (65.0 mmol) of the compound represented by [Chemical Formula 4-a] obtained from [Scheme 18] was dissolved in 210 ml of tetrahydrofuran under a stream of nitrogen, and stirred at -78° C. while stirring at -78° C., while 49 ml of 1.6 M normal-butyllithium ( 78.0 mmol) was slowly added dropwise, and when the dropwise addition was completed, the mixture was stirred for 1 hour while maintaining -78 ℃. Thereafter, 8.1 g (78.0 mmol) of trimethylborate was slowly added dropwise, and the mixture was raised to room temperature and stirred for 2 hours. Upon completion of the reaction, 100 ml of a 2 M aqueous hydrochloric acid solution was added dropwise at room temperature and stirred for 30 minutes. Thereafter, extraction was performed with ethyl acetate and water, and the organic layer was concentrated under reduced pressure and recrystallized from methylene chloride and hexane to obtain 12.5 g of a compound represented by [Chemical Formula 4-b]. (Yield 67%)

(3) Synthesis of a compound represented by [Formula 4-c]

A compound represented by [Chemical Formula 4-c] was synthesized by the following [Scheme 20].

[Scheme 20]

[Formula 1-c] [Formula 4-c]

Compound 20.0 g (74.7 mmol) represented by [Chemical Formula 1-c] obtained from [Scheme 3], 3-bromophenylboronic acid 15.0 g (35.6 mmol), tetrakis (triphenylphosphine) palladium 1.7 g (1.5 mmol), potassium carbonate 9.8 g (71.2 mmol), 1,4-dioxane 100 ml, toluene 100 ml, distilled water 50 ml, and stirred at 100° C. for 12 hours. When the reaction is completed, extraction is performed using ethyl acetate and distilled water. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from methylene chloride and acetone to obtain 20.3 g of a compound represented by [Chemical Formula 4-c]. (Yield 70%)

(4) Synthesis of a compound represented by [Formula 4-d]

A compound represented by [Chemical Formula 4-d] was synthesized by the following [Scheme 21].

[Scheme 21]

[Formula 4-c] [Formula 4-d]

20.3 g (52.3 mmol) of the compound represented by [Chemical Formula 4-c] obtained from [Scheme 20] was dissolved in 200 ml of tetrahydrofuran under a stream of nitrogen, and stirred at -78° C., while 39.2 ml of 1.6 M normal-butyllithium ( 62.7 mmol) was slowly added dropwise, and when the dropwise addition was completed, the mixture was stirred for 1 hour while maintaining -78°C. After that, 15.9 g (62.7 mmol) of iodine was slowly added dropwise, and then heated to room temperature and stirred for 1 hour. Upon completion of the reaction, 200 ml of an aqueous sodium thiosulfate solution was added dropwise, followed by stirring for 30 minutes. Thereafter, extraction was performed with ethyl acetate and water, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 19.8 g of a compound represented by [Chemical Formula 4-d]. (Yield 87%)

(5) Synthesis of a compound represented by [Formula 4-e]

A compound represented by [Chemical Formula 4-e] was synthesized by the following [Scheme 22].

[Scheme 22]

[Formula 4-d] [Formula 4-e]

[Chemical Formula 4-e] obtained from [Scheme 21] 19.8 g (45.5 mmol), 6-bromoindole 110.7 g (54.6 mmol), copper powder 5.8 g (91.0 mmol), 18-crown-6 2.4 g ( 9.1 mmol), potassium carbonate 12.6 g (191.0 mmol) were added in that order, and 1,2-dichlorobenzene 200 ml was added, followed by refluxing and stirring at 180° C. for 1 day. When the reaction was completed, the solution was concentrated under reduced pressure after high-temperature filtering, and the organic layer solution was recrystallized from methylene chloride and acetone to obtain 14.6 g of a compound represented by [Chemical Formula 4-e]. (Yield 64%)

(6) Synthesis of a compound represented by [Chemical Formula 110]

A compound represented by [Chemical Formula 110] was synthesized by the following [Scheme 23].

[Scheme 23]

[Formula 4-e] [Formula 110]

Compound 10.0 g (34.9 mmol) of [Chemical Formula 4-b] obtained from [Scheme 19], 14.6 g (29.1 mmol) of [Chemical Formula 4-e] obtained from [Scheme 22], tetrakis (triphenylphos) Palladium 672 mg (0.6 mmol), potassium carbonate 8.0 g (58.2 mmol), 1,4-dioxane 70 ml, toluene 70 ml, distilled water 30 ml, and stirred at 100° C. for 12 hours. When the reaction is completed, extraction is performed using methylene chloride and distilled water. The organic layer was concentrated under reduced pressure and recrystallized from methylene chloride and acetone to obtain 11.3 g of a compound represented by [Chemical Formula 110]. (Yield 66%)

MS [M] ⁺ 666

¹³ C NMR (75 MHz, CDCl ₃ ) δ:

104.8 105.4 109.5 109.9 111.6 116.8 118.7 118.9 119.3 119.4 119.8 121.3 121.4 124.3 125.5 126.6 127.5 128.3 129.2 129.3 129.8 131.1 131.2 134 134.7 135.5 136.8 141.6 142.4 143.7 145.4 145.9 170.7 172.2 [47C]

<Synthesis Example 5> Synthesis of a compound represented by [Chemical Formula 111]

Synthesis of the compound represented by [Chemical Formula 111]

A compound represented by [Chemical Formula 111] was synthesized by the following [Scheme 24].

[Scheme 24]

[Formula 5-a] [Formula 111]

2,4,6-trichloropyrimidine in place of 2,4,6-trichloro-1,3,5-triazine of Synthesis Example 4, and 4-bromophenyl instead of 3-bromophenylboronic acid Boronic acid was added and synthesized by the method of Synthesis Example 4 to obtain a compound represented by [Chemical Formula 111]. (Yield 57%)

MS [M] ⁺ 665

¹³ C NMR (75 MHz, CDCl ₃ ) δ:

104.8 105.4 108.8 109.5 109.9 111.6 114.1 116.8 118.9 119.3 119.4 119.8 121.4 125.5 126.6 127.5 128.1 128.3 128.7 129.2 129.3 131.5 134 135.5 135.8 136.8 138.7 141.6 143.7 145.4 145.9 155 164.6 [48C]

<Synthesis Example 6> Synthesis of a compound represented by [Chemical Formula 134]

Synthesis of the compound represented by [Formula 6-a]

A compound represented by [Chemical Formula 6-a] was synthesized by the following [Scheme 25].

[Scheme 25]

[Formula 6-a]

Slowly add 100.0 g (581.3 mmol) of 4-bromoaniline to 600 ml of water and 1 L of concentrated hydrochloric acid at 0°C. After dissolving 40.0 g (581.3 mmol) of sodium nitrite in 400 ml of distilled water, it was slowly dropped at 0 °C and stirred for 1 hour. To 600 g (2.9 mol) of tin (II) chloride dihydrate dissolved in 1.2 L of concentrated hydrochloric acid, the above mixture was slowly added at 0 °C, and then heated to room temperature and stirred for 3 hours. When the reaction was completed, the white solid was filtered and dried under reduced pressure at room temperature to obtain 114.0 g of a compound represented by [Chemical Formula 6-a]. (Yield 88%)

(2) Synthesis of a compound represented by [Formula 6-b]

A compound represented by [Chemical Formula 6-b] was synthesized by the following [Scheme 26].

[Scheme 26]

[Formula 6-a] [Formula 6-b]

68.5 g (306.5 mmol) of a compound represented by [Chemical Formula 6-a] obtained from [Scheme 25] and 22.1 g (306.5 mmol) of 2-butanone were added to 700 ml of ethyl alcohol and stirred at 65° C. for 1 hour. When the reaction was completed, it was lowered to room temperature, and the resulting solid was filtered and washed with ethyl alcohol. It dried under reduced pressure at room temperature to obtain 48.0 g of a compound represented by [Chemical Formula 6-b]. (Yield 70%)

(3) Synthesis of a compound represented by [Formula 6-c]

A compound represented by [Chemical Formula 6-c] was synthesized by the following [Scheme 27].

[Scheme 27]

[Formula 6-b] [Formula 6-c]

10.0 g (44.6 mmol) of the compound represented by [Chemical Formula 6-b] obtained from [Scheme 26] and 2.3 g (58.0 mmol) of 60% sodium hydride were added to 150 ml of dimethylformamide and stirred at room temperature for 30 minutes. . After that, 15.5 g (58.0 mmol) of chlorodiphenyltriazine was dissolved in 100 ml of dimethylformamide, slowly added dropwise, and stirred for 1 hour. When the reaction was completed, 100 ml of distilled water was added, filtered, and recrystallized to obtain 16.2 g of a compound represented by [Chemical Formula 6-c]. (Yield 80%)

(4) Synthesis of a compound represented by [Chemical Formula 134]

A compound represented by [Chemical Formula 134] was synthesized by the following [Scheme 28].

[Scheme 28]

[Formula 6-c] [Formula 4-b] [Formula 134]

Compound 10.0 g (22.0 mmol) represented by [Formula 6-c] obtained from [Scheme 27], 7.6 g (26.4 mmol) compound represented by [Formula 4-b] obtained from [Scheme 19], tetrakis ( Triphenylphosphine) palladium 508 mg (0.4 mmol), potassium carbonate 6.1 g (44.0 mmol), 1,4-dioxane 50 ml, toluene 50 ml, distilled water 20 ml, and stirred at 100° C. for 12 hours. When the reaction is completed, extraction is performed using methylene chloride and distilled water. The organic layer was concentrated under reduced pressure and recrystallized from methylene chloride and acetone to obtain 8.7 g of a compound represented by [Chemical Formula 134]. (Yield 64%)

MS [M] ⁺ 618

¹³ C NMR (75 MHz, CDCl ₃ ) δ:

9.5 10.7 105.4 107.6 109.5 111.6 116.8 119.2 119.4 119.8 121.4 125.5 126.6 127.5 127.8 129.2 129.3 131.1 133.1 134 134.7 135.5 136.8 143.7 144 145.4 172.1 178.8 [43C]

<Synthesis Example 7> Synthesis of a compound represented by [Chemical Formula 146]

A compound represented by [Chemical Formula 146] was synthesized by the following [Scheme 29].

[Scheme 29]

[Formula 7-a] [Formula 4-b] [Formula 146]

2,4,6-trichloropyrimidine in place of 2,4,6-trichloro-1,3,5-triazine of Synthesis Example 4, and 4-bromophenyl instead of 3-bromophenylboronic acid The compound represented by [Chemical Formula 6-b] was added to the boronic acid, instead of 6-bromoindole, and synthesized by the method of Synthesis Example 4 to obtain a compound represented by [Chemical Formula 146]. (Yield 52%)

MS [M] ⁺ 693

¹³ C NMR (75 MHz, CDCl ₃ ) δ:

9.5 10.7 105.4 108.8 109.5 110 111.6 114.1 116.8 119.4 119.8 121.4 125.5 126.6 127.5 128.1 128.7 129.2 129.3 130.2 131.5 134 135.5 135.8 136.3 136.8 143.7 145 145.4 151 155 164.6 [50C]

<Synthesis Example 8> Synthesis of a compound represented by [Chemical Formula 157]

(1) Synthesis of a compound represented by [Formula 8-a]

A compound represented by [Chemical Formula 8-a] was synthesized by the following [Scheme 30].

[Scheme 30]

[Formula 8-a]

2,4,6-trichloro-1,3,5-triazine 20.0 g (109 mmol), phenylboronic acid 13.3 g (109 mmol) and tetrakis (triphenylphosphine) palladium 2.5 g (2.2 mmol), Potassium carbonate 60.3 g (436 mmol) was added to a mixed solvent of 600 ml of tetrahydrafuran, 400 ml of toluene, and 400 ml of distilled water, and stirred for 9 hours and refluxed. When the reaction is complete, the organic layer is washed with a saturated aqueous sodium chloride solution after extraction and dried over anhydrous sodium sulfate. The organic solvent was distilled off under reduced pressure, and then recrystallized with hexane to obtain 20.7 g of a compound represented by [Chemical Formula 8-a]. (Yield 84%)

(2) Synthesis of a compound represented by [Formula 8-b]

A compound represented by [Chemical Formula 8-b] was synthesized by the following [Scheme 31].

[Scheme 31]

[Formula 8-a] [Formula 8-b]

20.7 g (91.56 mmol) of the compound represented by [Chemical Formula 8-a] obtained from [Scheme 30], benzothiophene-4-boronic acid 20.9 g (91.56 mmol) and tetrakis (triphenylphosphine) palladium 2.1 g (1.8 mmol) and potassium carbonate 25.3 g (183.1 mmol) were added to a mixed solvent of 600 ml of tetrahydrafuran, 400 ml of toluene, and 400 ml of distilled water, and stirred for 12 hours and refluxed. When the reaction is complete, the organic layer is washed with a saturated aqueous sodium chloride solution after extraction and dried over anhydrous sodium sulfate. The organic solvent was distilled off under reduced pressure, and then recrystallized with methylene chloride and hexane to obtain 23.6 g of a compound represented by [Chemical Formula 8-b]. (Yield 69%)

(3) Synthesis of a compound represented by [Formula 8-c]

A compound represented by [Chemical Formula 8-c] was synthesized by the following [Scheme 32].

[Scheme 32]

[Formula 8-b] [Formula 8-c]

Compound 20.0 g (53.5 mmol) represented by [Chemical Formula 8-b] obtained from [Scheme 31], 4-bromophenylboronic acid 12.9 g (61.2 mmol), tetrakis (triphenylphosphine) palladium 1.2 g (1.1 mmol), potassium carbonate 14.8 g (107 mmol), 1,4-dioxane 100 ml, toluene 100 ml, distilled water 50 ml, and stirred at 100° C. for 12 hours. When the reaction is completed, extraction is performed using ethyl acetate and distilled water. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized from methylene chloride and acetone to obtain 19.3 g of a compound represented by [Chemical Formula 8-c]. (73% yield)

(4) Synthesis of a compound represented by [Formula 8-d]

A compound represented by [Chemical Formula 8-d] was synthesized by the following [Scheme 33].

[Scheme 33]

[Formula 8-c] [Formula 8-d]

After dissolving 19.3 g (39.1 mmol) of the compound represented by [Chemical Formula 8-c] obtained from [Scheme 32] in 200 ml of tetrahydrofuran under a stream of nitrogen, 29.3 ml of 1.6 M normal-butyllithium while stirring at -78°C ( 46.9 mmol) was slowly added dropwise, and when the dropwise addition was completed, the mixture was stirred for 1 hour while maintaining -78°C. After that, 11.9 g (46.9 mmol) of iodine was slowly added dropwise, and then heated to room temperature and stirred for 1 hour. Upon completion of the reaction, 200 ml of an aqueous sodium thiosulfate solution was added dropwise, followed by stirring for 30 minutes. Thereafter, extraction was performed with ethyl acetate and water, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 16.8 g of a compound represented by [Chemical Formula 1-d]. (79% yield)

(5) Synthesis of a compound represented by [Formula 8-e]

A compound represented by [Chemical Formula 8-e] was synthesized by the following [Scheme 34].

[Scheme 34]

[Formula 8-d] [Formula 8-e]

[Chemical Formula 8-d] compound 16.8 g (30.9 mmol) obtained from [Scheme 33], 8.3 g (37.1 mmol) of the compound represented by [Chemical Formula 6-b] obtained from [Scheme 26], copper powder 3.9 g ( 61.8 mmol), 18-crown-6 1.6 g (6.18 mmol), potassium carbonate 12.8 g (92.7 mmol) were added in that order, and 170 ml of 1,2-dichlorobenzene was added, followed by refluxing and stirring at 180° C. for 1 day. Let it. When the reaction was completed, the solution was concentrated under reduced pressure after high-temperature filtering, and the organic layer solution was recrystallized from methylene chloride and acetone to obtain 13.2 g of a compound represented by [Chemical Formula 8-e]. (Yield 67%)

(6) Synthesis of a compound represented by [Chemical Formula 157]

A compound represented by [Chemical Formula 157] was synthesized by the following [Scheme 35].

[Scheme 35]

[Formula 8-e] [Formula 157]

13.2 g (20.7 mmol) of the compound represented by [Chemical Formula 8-e] obtained from [Scheme 34], 7.1 g (24.8 mmol) of [Chemical Formula 4-b] obtained from [Scheme 19], tetrakis (triphenylphos) Pin) palladium 478 mg (0.4 mmol), potassium carbonate 5.7 g (41.4 mmol), 1,4-dioxane 70 ml, toluene 70 ml, distilled water 30 ml, and stirred at 100° C. for 12 hours. When the reaction is completed, extraction is performed using methylene chloride and distilled water. The organic layer was concentrated under reduced pressure and recrystallized from methylene chloride and acetone to obtain 9.7 g of a compound represented by [Chemical Formula 157]. (59% yield)

MS [M] ⁺ 800

¹³ C NMR (75 MHz, CDCl ₃ ) δ:

9.5 10.7 105.4 109.5 110 111.6 114.1 116.8 119.4 119.7 119.8 121.4 122.3 122.8 123.2 124.3 124.4 124.8 125.5 126.4 126.6 127.5 128.1 129.2 129.3 130.2 130.6 131.1 131.5 134 134.7 135.5 136.3 136.8 139.5 142.4 143.7 145 145.4 151 170.7 171.7 172.7 [55C]

<Synthesis Example 9> Synthesis of a compound represented by [Chemical Formula 166]

Synthesis of a compound represented by [Chemical Formula 166]

A compound represented by [Chemical Formula 166] was synthesized by the following [Scheme 36].

[Scheme 36]

[Formula 9-a] [Formula 166]

In [Scheme 31] of Synthesis Example 8, instead of benzothiophene-4-boronic acid, a compound represented by [Chemical Formula 4-b] obtained from [Scheme 19] was added, and synthesized by the method of Synthesis Example 8 [ A compound represented by Chemical Formula 166] was obtained. (Yield 49%)

MS [M] ⁺ 859

¹³ C NMR (75 MHz, CDCl ₃ ) δ:

9.5 10.7 105.4 109.5 110 111.6 114.1 116.4 116.8 119 119.4 119.8 121.4 125.5 126.6 127.5 128.1 129.2 129.3 129.7 130.2 131.1 131.5 134 134.7 135.5 136.3 136.8 143.7 145 145.4 151 170.7 171.7 172.7 [61C]

<Synthesis Example 10> Synthesis of a compound represented by [Chemical Formula 187]

(1) Synthesis of a compound represented by [Formula 10-a]

A compound represented by [Chemical Formula 10-a] was synthesized by the following [Scheme 37].

[Scheme 37]

[Formula 10-a]

At room temperature, 2-aminobenzonitrile (20.0 g, 169 mmol) and 140 mL of tetrahydrofuran were added to a round bottom flask under a nitrogen stream, followed by stirring. 112.9 mL (339 mmol) of phenyl magnesium bromide (3.0 M in Et ₂ O) was added dropwise. After reflux stirring for about 1 hour, the temperature was set to 0°C. Ethyl chloroformate (22.0g, 203mmol) was added dropwise and stirred under reflux for about 1 hour. An aqueous ammonium chloride solution was added until it became slightly acidic, and the resulting solid was filtered and washed with water and heptane to obtain 30.1 g of [Formula 10-a]. (Yield: 80%)

(2) Synthesis of a compound represented by [Formula 10-b]

A compound represented by [Chemical Formula 10-b] was synthesized by the following [Scheme 38].

[Scheme 38]

[Formula 10-b]

At room temperature, the synthesized [intermediate 10-a] (30.0 g, 135 mmol) and about 80 mL of phosphorus oxychloride were added to a round bottom flask under a nitrogen stream, followed by stirring. After reflux stirring overnight, the temperature was cooled to -20℃ the next day, and water was slowly added dropwise about 400mL. The resulting solid was filtered and washed with water, methanol, and heptane. 14.6g of [Chemical Formula 10-b] was obtained by recrystallization from toluene and heptane. (Yield: 44.9%)

(3) Synthesis of a compound represented by [Formula 10-c]

A compound represented by [Chemical Formula 10-c] was synthesized by the following [Scheme 39].

[Scheme 39]

[Formula 10-c]

10.5g of [Chemical Formula 10-c] was synthesized by the same method using [Chemical Formula 10-b] instead of [Chemical Formula 1-c] used in [Scheme 5]. (Yield: 84%)

(4) Synthesis of a compound represented by [Chemical Formula 187]

A compound represented by [Chemical Formula 187] was synthesized by the following [Scheme 40].

[Scheme 40]

[Formula 187]

4.5g of [Chemical Formula 187] was synthesized by using the synthesized [Chemical Formula 10-c] instead of [Chemical Formula 1-e] used in [Scheme 6]. (Yield: 48%)

MS [M] ⁺ 563

¹³ C NMR (75 MHz, CDCl ₃ ) δ:

103 104.8 109.5 109.9 111.6 116.8 118.9 119.3 119.4 119.8 121.3 121.4 125.5 126.6 127.4 127.5 127.7 128.3 128.5 128.7 129.2 129.3 131.8 132.3 133 133.1 138.7 141.6 143.7 144.4 145.9 149.3 155.8 161 [40C]

<Synthesis Example 11> Synthesis of a compound represented by [Chemical Formula 188]

(1) Synthesis of a compound represented by [Formula 11-a]

A compound represented by [Chemical Formula 11-a] was synthesized by the following [Scheme 41].

[Scheme 41]

[Formula 11-a]

Under a stream of nitrogen, 1-nitronaphthalene (50.0 g, 289 mmol), ethyl cyanoacetate (98.0 g, 866 mmol), potassium cyanide (20.7 g, 318 mmol), potassium hydroxide (32.4 g, 577 mmol) in a round bottom flask immersed in water And stirred. 100 mL of dimethylformamide was added, the temperature was raised to 60°C, and the mixture was stirred overnight. The next day, the change of TLC was checked and the temperature of the flask was set to room temperature. The reaction solution was concentrated under reduced pressure to remove all possible dimethylformamide. The concentrate was transferred to a reactor with a small amount of dichloromethane, and 500 mL of 5% aqueous sodium hydroxide solution was added thereto, followed by stirring. After reflux stirring for about 1 hour, the temperature was brought to room temperature. Extracted with ethyl acetate and water. It was separated by column chromatography using ethyl acetate and heptane. Recrystallized from toluene and heptane to give 24.6g (yield 50.7%) of [Chemical Formula 11-a] as a white solid.

(2) Synthesis of a compound represented by [Formula 11-b]

A compound represented by [Chemical Formula 11-b] was synthesized by the following [Scheme 42].

[Scheme 42]

[Formula 11-b]

Instead of the 2-aminobenzonitrile used in [Scheme 37], the synthesized [Chemical Formula 11-a] was used and synthesized in the same manner as [Scheme 37] to [Scheme 38] to obtain 21g of [Formula 11-b]. (Yield: 74.5%)

(3) Synthesis of a compound represented by [Formula 11-c]

A compound represented by [Chemical Formula 11-c] was synthesized by the following [Scheme 43].

[Scheme 43]

[Formula 11-c]

9.8g of [Chemical Formula 11-c] was synthesized in the same manner using [Chemical Formula 11-b] instead of [Chemical Formula 1-c] used in [Scheme 5]. (Yield: 82%)

(4) Synthesis of a compound represented by [Chemical Formula 188]

A compound represented by [Chemical Formula 188] was synthesized by the following [Scheme 44].

[Scheme 44]

[Chemical Formula 188]

Instead of [Chemical Formula 1-e] used in [Scheme 6], 7.6g of [Chemical Formula 188] was synthesized in the same manner using the synthesized [Chemical Formula 11-c]. (Yield: 55%)

MS [M] ⁺ 613

¹³ C NMR (75 MHz, CDCl ₃ ) δ:

103 104.8 109.5 109.9 111.6 116.8 118.9 119.3 119.4 119.8 121.3 121.4 124.9 125.5 126.6 127.2 127.3 127.4 127.5 127.9 128.3 128.7 129.2 129.3 131.8 133 133.1 134.4 138.7 141.6 143.7 144.4 145.9 150 155.8 161 [44C]

<Synthesis Example 12> Synthesis of a compound represented by [Chemical Formula 191]

(1) Synthesis of a compound represented by [Chemical Formula 12-a]

A compound represented by [Chemical Formula 12-a] was synthesized by the following [Scheme 45].

[Scheme 45]

[Formula 12-a]

[Chemical Formula 11-a] used in [Scheme 42] was synthesized in the same manner using 3-amino-2-naphtonitrile instead of [Chemical Formula 12-a] to obtain 20g. (Yield: 71%)

(2) Synthesis of a compound represented by [Chemical Formula 12-b]

A compound represented by [Chemical Formula 12-b] was synthesized by the following [Scheme 46].

[Scheme 46]

[Formula 12-b]

10.7g of [Chemical Formula 12-b] was synthesized in the same manner using [Chemical Formula 12-a] instead of [Chemical Formula 1-c] used in [Scheme 5]. (Yield: 86%)

(4) Synthesis of a compound represented by [Chemical Formula 191]

A compound represented by [Chemical Formula 191] was synthesized by the following [Scheme 47].

[Scheme 47]

[Chemical Formula 191]

6.8g of [Chemical Formula 191] was synthesized in the same manner using [Chemical Formula 12-b] instead of [Chemical Formula 1-e] used in [Scheme 6]. (Yield: 52%)

MS [M] ⁺ 613

¹³ C NMR (75 MHz, CDCl ₃ ) δ:

103 104.8 109.5 109.9 111.6 116.8 118.9 119.3 119.4 119.8 121.3 121.4 125.5 126.6 127.2 127.3 127.5 128.2 128.3 128.6 128.7 129.2 129.3 131.8 133 133.1 133.6 134.4 138.7 141.6 143.7 144.4 145.9 149.3 155.8 161 [44C]

< Example 1 to 9> Preparation of organic light emitting diode

The ITO glass was patterned so that the light emitting area was 2 mm × 2 mm in size and washed. After mounting the substrate in a vacuum chamber, the base pressure was 1×10 ^-6 torr, and then the organic material was added to the ITO on DNTPD (700 Å), NPD (300 Å), the compound synthesized by Synthesis Examples 1 to 9 + Ir ( ppy) ₃ (10%) (300 Å), Alq ₃ (350 Å), LiF (5 Å), and Al (1,000 Å) were formed in the order, and measured at 0.4 mA.

[DNTPD] [NPD]

[Ir(ppy) ₃ ] [Alq ₃ ]

< Comparative example 1>

The organic light-emitting diode device for Comparative Example 1 was fabricated in the same manner as in the device structures of Examples 1 to 9 except that CBP, which is commonly used as a phosphorescent host material, was used instead of the compound prepared by the invention. The structure of is as follows.

[CBP]

For the organic electroluminescent devices manufactured according to Examples 1 to 9 and Comparative Example 1, voltage, current density, luminance, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T80 means the time it takes for the luminance to decrease from the initial luminance (7000nit) to 80%.

division Host Dopant Doping concentration% V Cd/m ² CIEx CIEy T ₈₀ (Hr) Comparative Example 1 CBP Ir(ppy) ₃ 10 7.9 3800 0.297 0.624 68 Example 1 10 Ir(ppy) ₃ 10 4.0 5040 0.312 0.619 196 Example 2 92 Ir(ppy) ₃ 10 3.9 5110 0.309 0.625 136 Example 3 109 Ir(ppy) ₃ 10 4.1 5130 0.301 0.611 148 Example 4 110 Ir(ppy) ₃ 10 3.7 5050 0.315 0.626 194 Example 5 111 Ir(ppy) ₃ 10 3.6 4890 0.307 0.617 155 Example 6 134 Ir(ppy) ₃ 10 4.4 5170 0.323 0.620 170 Example 7 146 Ir(ppy) ₃ 10 4.1 5130 0.302 0.612 172 Example 8 157 Ir(ppy) ₃ 10 4.5 4980 0.306 0.620 154 Example 9 166 Ir(ppy) ₃ 10 4.6 5180 0.315 0.613 122

As shown in [Table 1], the organic electroluminescent device including the heterocyclic compounds prepared according to Examples 1 to 8 as a host material has a maximum driving voltage (V) compared to Comparative Example 1 in which the host material is CBP. 4V is low, the luminous efficiency (Cd/m2) has increased by more than 40%, and has a long life (T ₈₀ ), so it can be seen that it can be usefully used for display devices, display devices, and lighting.

<Examples 10 to 12> Preparation of organic electroluminescent devices including compounds synthesized by Synthesis Examples 10 to 12

The ITO glass was patterned so that the light emitting area was 2 mm x 2 mm and washed. After mounting the substrate in a vacuum chamber, the base pressure was 1×10 ^-6 torr, and then the organic material was placed on the ITO with DNTPD (700 Å), NPD (300 Å), the compound synthesized by Synthesis Examples 10 to 12 + (piq ) ₂ Ir (acac) (10%) (300 Å), Alq ₃ (350 Å), LiF (5 Å), Al (1,000 Å) were formed in the order, and the measurement was performed at 0.4 mA.

The structure of the (piq) ₂ Ir(acac) is as follows.

[(piq) ₂ Ir(acac)]

<Example 13> In the device structures of Examples 10 to 12, [Chemical Formula 191] was used for the light emitting layer, and [PTOEP] was used instead of [(piq) ₂ Ir(acac)], and the same was prepared [ The structure of [PTOEP] is as follows.

[PTOEP]

<Comparative Example 2>

The organic light emitting diode device for Comparative Example 2 was fabricated in the same manner as in the device structures of Examples 10 to 12, except that CBP was used instead of the compound prepared by the present invention as a host material.

For the organic electroluminescent devices manufactured according to Examples 10 to 12 and Comparative Example 2, voltage, current density, luminance, color coordinates and lifetime were measured, and the results are shown in Table 2 below. T90 refers to the time it takes for the luminance to decrease from the initial luminance (3700nit) to 90%.

division Host Dopant Doping concentration% V Cd/㎡ CIEx CIEy T ₉₀ (Hr) Example 10 187 (piq) ₂ Ir(acac) 10 4.3 1890 0.669 0.328 1680 Example 11 188 (piq) ₂ Ir(acac) 10 3.7 1970 0.675 0.322 1580 Example 12 191 (piq) ₂ Ir(acac) 10 3.8 1850 0.671 0.326 1535 Example 13 191 PTOEP 10 3.8 1810 0.657 0.321 1510 Comparative Example 2 CBP (piq) ₂ Ir(acac) 10 3.7 410 0.667 0.328 140

As shown in [Table 2], the organic electroluminescent device including the heterocyclic compound prepared according to Examples 10 to 13 of the present invention as a host material was compared to Comparative Example 2 in which the host material was CBP. ) Is low, has excellent luminous efficiency (Cd/m2) and long life (T ₉₀ ), so it can be seen that it can be usefully used for display devices, display devices, and lighting.

Claims (12)

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

In the above [Formula 1],
Y is any one selected from the group consisting of O, S, CR ₂ R ₃ , NR ₄ and SiR ₅ R ₆ ,
Ar is selected from the group consisting of 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, p is an integer of 1 to 3, and when p is 2 or more, plural Ar of are each the same or different from each other,
L is a single bond or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms (however, excluding an anthracenylene group, n is an integer of 1),
X ₁ to X ₂ is the same as or different from each other, and each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 40 carbon atoms,
X ₃ to X ₁₀ are the same as or different from each other, and each independently hydrogen,
X ₁₁ to X ₁₄ is the same as or different from each other, and each independently hydrogen, deuterium, a halogen atom, 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, a substituted or unsubstituted A heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, -SiR ₇ R ₈ R ₉ and -NR ₁₀ R ₁₁ It is selected from the group consisting of,
R ₁ to R ₁₁ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted carbon number It is selected from the group consisting of 2 to 30 heteroaryl groups. The method of claim 1,
Each of X ₁₁ to X ₁₄ is connected to a substituent adjacent to each other to form an alicyclic, aromatic monocyclic or polycyclic ring. The method of claim 2,
A heterocyclic compound, characterized in that the formed alicyclic, aromatic monocyclic or polycyclic carbon atoms are substituted with any one or more heteroatoms selected from N, S and O. The method of claim 1,
The R ₁ to R ₁₁ , X ₁₁ to X ₁₄ , L, Ar are each independently a deuterium atom, a cyano group, a halogen atom, a hydroxy group, a nitro group, an alkyl group having 1 to 40 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, and 1 to 40 alkylamino group, C 6 to C 40 arylamino group, C 3 to C 40 heteroarylamino group, C 1 to C 40 alkylsilyl group, C 6 to C 40 arylsilyl group, C 6 to C 40 aryl group, It is further substituted with one or more substituents selected from the group consisting of a C3-C40 aryloxy group, a C3-C40 heteroaryl group, a germanium group, phosphorus and boron,
The heterocyclic compound, characterized in that the substituents are bonded to each other with adjacent substituents to form a saturated or unsaturated ring, or are attached or fused together in a pendant manner. delete delete The method of claim 1,
The heterocyclic compound represented by [Chemical Formula 1] is a heterocyclic compound characterized in that it is one of compounds represented by the following [Chemical Formula 2] to [Chemical Formula 9]:
[Chemical Formula 2] [Chemical Formula 3]

[Chemical Formula 4] [Chemical Formula 5]

[Formula 6] [Formula 7]

[Chemical Formula 8] [Chemical Formula 9]

In the above [Formula 2] to [Formula 9],
Y, X ₁ To X ₁₄ , R ₁ , Ar and p are the same as defined in [Chemical Formula 1]. The method of claim 1,
The heterocyclic compound represented by [Chemical Formula 1] is any one selected from the group represented by the following [Chemical Formula 10] to [Chemical Formula 187]:
[Formula 10] [Formula 11]

[Formula 12] [Formula 13]

[Formula 14] [Formula 15]

[Formula 16] [Formula 17]

[Chemical Formula 18] [Chemical Formula 19]

[Formula 20] [Formula 21]

[Formula 22] [Formula 23]

[Formula 24] [Formula 25]

[Formula 26] [Formula 27]

[Formula 28] [Formula 29]

[Chemical Formula 30] [Chemical Formula 31]

[Formula 32] [Formula 33]

[Formula 34] [Formula 35]

[Chemical Formula 36] [Chemical Formula 37]

[Chemical Formula 38] [Chemical 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]

[Chemical Formula 54] [Chemical Formula 55]

[Chemical Formula 56] [Chemical Formula 57]

[Chemical Formula 58] [Chemical Formula 59]

[Chemical Formula 60] [Chemical Formula 61]

[Formula 62] [Formula 63]

[Formula 64] [Formula 65]

[Chemical Formula 66] [Chemical Formula 67]

[Chemical Formula 68] [Chemical Formula 69]

[Formula 70] [Formula 71]

[Chemical Formula 72] [Chemical Formula 73]

[Formula 74] [Formula 75]

[Chemical Formula 76] [Chemical 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]

[Chemical Formula 88] [Chemical Formula 89]

[Formula 90] [Formula 91]

[Formula 92] [Formula 93]

[Formula 94] [Formula 95]

[Chemical Formula 96] [Chemical Formula 97]

[Chemical Formula 98] [Chemical Formula 99]

[Chemical Formula 100] [Chemical Formula 101]

[Formula 102] [Formula 103]

[Chemical Formula 104] [Chemical Formula 105]

[Formula 106] [Formula 107]

[Chemical Formula 108] [Chemical Formula 109]

[Chemical Formula 110] [Chemical Formula 111]

[Chemical Formula 112] [Chemical Formula 113]

[Chemical Formula 114] [Chemical Formula 115]

[Chemical Formula 116] [Chemical Formula 117]

[Chemical Formula 118] [Chemical Formula 119]

[Chemical Formula 120] [Chemical Formula 121]

[Formula 122] [Formula 123]

[Chemical Formula 124] [Chemical Formula 125]

[Chemical Formula 126] [Chemical Formula 127]

[Chemical Formula 128] [Chemical Formula 129]

[Chemical Formula 130] [Chemical Formula 131]

[Chemical Formula 132] [Chemical Formula 133]

[Formula 134] [Formula 135]

[Chemical Formula 136] [Chemical Formula 137]

[Chemical Formula 138] [Chemical Formula 139]

[Chemical Formula 140] [Chemical Formula 141]

[Chemical Formula 142] [Chemical Formula 143]

[Formula 144] [Formula 145]

[Chemical Formula 146] [Chemical Formula 147]

[Formula 148] [Formula 149]

[Chemical Formula 150] [Chemical Formula 151]

[Formula 152] [Formula 153]

[Chemical Formula 154] [Chemical 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]

[Chemical Formula 168] [Chemical Formula 169]

[Chemical Formula 170] [Chemical Formula 171]

[Formula 172] [Formula 173]

[Formula 174] [Formula 175]

[Formula 176] [Formula 177]

[Formula 178] [Formula 179]

[Chemical Formula 180] [Chemical Formula 181]

[Chemical Formula 182] [Chemical Formula 183]

[Chemical Formula 184] [Chemical Formula 185]

[Formula 186] [Formula 187]

A first electrode; A second electrode facing the first electrode; And one or more organic layers interposed between the first electrode and the second electrode,
The organic layer is an organic electroluminescent device comprising at least one heterocyclic compound represented by [Chemical Formula 1] according to claim 1. The method of claim 9,
The organic layer comprises at least one layer selected from a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time, a light emitting layer, an electron transport layer, and an electron injection layer. The method of claim 10,
The emission layer includes at least one host compound and at least one dopant compound, and the host compound is an organic electroluminescent device, wherein the host compound is a heterocyclic compound represented by [Chemical Formula 1]. The method of claim 9,
An organic electroluminescent device, characterized in that the organic layer further includes at least one organic emission layer emitting red, green, or blue light to emit white light.

Images