KR20230040969A - Organic compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, to a novel compound with excellent luminous ability, and an organic electroluminescent device with improved characteristics such as high luminous efficiency, low driving voltage, and long lifespan by including the same in one or more organic layers.

Description

Organic compound and organic electroluminescent device using the same {ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME}

The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, to an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, lifespan, etc. It is about.

Research on organic electroluminescent devices, which led to blue electroluminescence using an anthracene single crystal in 1965 from Bernanose's observation of organic thin film emission in the 1950s, was divided into a hole layer and a functional layer of light emitting layer by Tang in 1987. An organic electroluminescent device with a layered structure is presented. Since then, in order to make a high-efficiency, long-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.

In the organic electroluminescent device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons are injected into the organic material layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. At this time, the material used as the organic material layer may be classified according to its function into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like.

Materials for forming the light emitting layer of the organic electroluminescent device may be classified into blue, green, and red light emitting materials according to the light emitting color. In addition, yellow and orange light emitting materials are also used as light emitting materials for implementing better natural colors. In addition, in order to increase color purity and increase light emitting efficiency through energy transfer, a host/dopant system may be used as a light emitting material.

The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of such a phosphorescent material can theoretically improve luminous efficiency up to 4 times compared to fluorescence, so attention is focused on phosphorescent host materials as well as phosphorescent dopants.

Until now, NPB, BCP, Alq ₃ , etc. have been widely known as materials used in hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives have been reported as fluorescent dopant/host materials as light emitting materials. . In particular, phosphorescent materials that have a great advantage in terms of efficiency improvement among light emitting materials include metal complex compounds containing Ir such as Firpic, Ir(ppy) ₃ , and (acac)Ir(btp) ₂ as blue, green, and red dopant materials. is being used as So far, CBP has shown excellent properties as a phosphorescent host material.

However, conventional light emitting materials are advantageous in terms of light emitting properties, but have low glass transition temperatures and very poor thermal stability, so they are not satisfactory in terms of lifespan in organic light emitting devices. Therefore, there is a demand for the development of light emitting materials having excellent performance.

Japanese Laid-Open Patent Publication No. 2001-160489

In order to solve the above problems, the present invention can be applied to an organic electroluminescent device, and an object of the present invention is to provide a novel organic compound having excellent light emitting ability by satisfying the required appropriate range of energy level, electrochemical stability, thermal stability, etc. to be

In addition, an object of the present invention is to provide an organic electroluminescent device exhibiting a low driving voltage and high luminous efficiency, including the novel organic compound, and having an improved lifetime.

In order to achieve the above object, the present invention provides a compound represented by Formula 1 below.

A compound represented by Formula 1 below:

In Formula 1,

X is NR ₂ or CR ₃ R ₄ ;

L is a single bond or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;

Y is O or S;

Z ₁ to Z ₃ are the same as or different from each other, and are each independently N or CR ₅ , at least one of which is N;

n is an integer from 0 to 4;

R ₁ to R ₅ , Ar ₁ and Ar ₂ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ ~ C ₄₀ alkyl group, a C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms hetero Aryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl It is selected from the group consisting of a boron group, a C ₆ ~ C ₆₀ arylboron group, a C ₆ ~ C ₆₀ arylphosphine group, a C ₆ ~ C ₆₀ arylphosphine oxide group, and a C ₆ ~ C ₆₀ arylamine group, Or they may form a condensed ring with an adjacent group,

Arylene group and heteroarylene group of L, R ₁ to R ₅ , Ar ₁ and Ar ₂ Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryl An oxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group, and an arylamine group are each independently deuterium, halogen, cyano group, nitro group, amino group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl Group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl Silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group and C ₆ ~ C ₆₀ substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when the substituents are plural, they are the same as or different from each other.

In addition, the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers includes the compound represented by Formula 1. An electroluminescent device is provided. Here, the organic material layer including the compound represented by Chemical Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and an electron injection layer. In this case, the compound represented by Chemical Formula 1 may be used as a phosphorescent host of the light emitting layer.

Since the compound represented by Chemical Formula 1 of the present invention has excellent thermal stability and emission characteristics, it can be used as a material for an organic layer of an organic electroluminescent device.

In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having a lower driving voltage, higher efficiency, and longer lifespan than conventional host materials can be manufactured, and further performance and lifespan can be produced. This improved full color display panel can also be manufactured.

Hereinafter, the present invention will be described in detail.

1. Organic compounds

Specifically, the compound represented by Formula 1 is dibenzofuran (Y=O) or dibenzothiophene (Y=S) when an electron withdrawing group is bonded to position 3, any one of positions 5 to 8 An electron pusher may be coupled to the position. The compound represented by Formula 1 may be embodied by any one of Formulas 2 to 5 below.

In Chemical Formulas 2 to 5, X, L, Y, Z ₁ to Z ₃ , n, R ₁ , Ar ₁ and Ar ₂ are each as defined in Chemical Formula 1 above.

In the compound represented by Formula 1, X is NR ₂ or CR ₃ R ₄ . In this case, when X is CR ₃ R ₄ , it may be fluorene, or R ₃ and R ₄ may combine to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, or a condensed heteroaromatic ring.

The L is a linking portion bonded to an electron locking group, and is a single bond, or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms, and is a single bond or an arylene group desirable.

In this case, L may bind to any one of R ₂ to R ₄ or to a benzene ring including R ₁ . When L and R ₁ are bonded, n is an integer from 1 to 3.

Here, as the binding position of the electron locking group moves from No. 5 to No. 8 of dibenzofuran or dibenzothiophene, the energy band gap of the compound represented by Formula 1 increases, the HOMO level is maintained, and the LUMO level can be increased. . Accordingly, the compound represented by Chemical Formula 1 is preferably a green light-emitting layer material in which an electron blocking group is bonded to the 5-position of dibenzofuran or dibenzothiophene (see Chemical Formula 2 above) so as to exhibit an appropriate LUMO level.

The electron blocking group may be carbazole, fluorene, condensed fluorene having a spiro structure, and the like. At this time, it is preferable that the electron blocking group is carbazole having a high electron donating property.

The compound of Formula 1 containing such an electron blocking group may be embodied by any one of Formulas 6 to 14 below.

In Chemical Formulas 6 to 14, L, Y, Z ₁ to Z ₃ , n, R ₁ , Ar ₁ and Ar ₂ are each as defined in Chemical Formula 1 above.

In the compound represented by Formula 1, Z ₁ to Z ₃ are the same as or different from each other, and each independently represent N or CR ₅ , at least one of which is N. More specifically, Z ₁ to Z ₃ contain at least one N, and the electron withdrawing group may be pyridine, pyrimidine or triazine. At this time, it is preferable that triazine has a large electron withdrawing property.

Said n is an integer of 0-4. At this time, when n is 0, it means that hydrogen is not substituted with the substituent R ₁ , and when n is an integer of 1 to 4, it means that hydrogen is substituted with the substituent R ₁ .

Wherein R ₁ to R ₅ , Ar ₁ and Ar ₂ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ ~C ₄₀ alkyl group, and a C ₂ ~C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms Heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ An alkyl boron group, a C ₆ ~ C ₆₀ aryl boron group, a C ₆ ~ C ₆₀ aryl phosphine group, a C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ selected from the group consisting of an arylamine group, or , or they may form condensed rings with adjacent groups. At this time, as an adjacent group, R ₁ and another R ₁ or R ₃ and R ₄ may be bonded to each other to form a condensed ring.

Preferably, R ₁ to R ₅ are the same as or different from each other, and each independently represents hydrogen, a C ₁ ~ C ₄₀ alkyl group, a C ₆ ~ C ₆₀ aryl group, or a heteroaryl group having 5 to 60 nuclear atoms. , C ₆ ~ C ₆₀ aryloxy group, C ₆ ~ C ₆₀ arylsilyl group, C ₆ ~ C ₆₀ aryl boron group, and C ₆ ~ C ₆₀ selected from the group consisting of arylamine group, or they are combined with adjacent groups Can form condensed rings.

More preferably, R ₁ to R ₅ are the same as or different from each other, and may be each independently selected from the group consisting of hydrogen, a C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. .

Also, preferably, Ar ₁ and Ar ₂ may be substituents selected from the group consisting of the following structural formulas.

In the above structural formula, * means a site bonded to Formula 1.

More preferably, at least one of Ar ₁ and Ar ₂ may be a heteroaryl group. More specifically, either one of Ar ₁ and Ar ₂ may be a heteroaryl group and the other may be an aryl group, or both Ar ₁ and Ar ₂ may be heteroaryl groups.

Compounds represented by Formula 1 of the present invention described above are exemplified by compounds A-1 to A-109, B-1 to B-129, C-1 to C-69, D-1 to D-109, E -1 to E-129, F-1 to F-73, G-1 to G-109, H-1 to H-129, I-1 to I-73, J-1 to J-109, K-1 to K-129 and L-1 to L-73. However, the compound represented by Formula 1 of the present invention is not limited by those exemplified below.

In the present invention, “alkyl” means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples of such alkyl include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

In the present invention, “alkenyl” refers to a monovalent substituent derived from a straight-chain or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples of such alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.

In the present invention, “alkynyl” refers to a monovalent substituent derived from a straight-chain or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples of such alkynyl include, but are not limited to, ethynyl and 2-propynyl.

In the present invention, “cycloalkyl” means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

In the present invention, “heterocycloalkyl” means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and one or more carbons in the ring, preferably 1 to 3 carbons, are N, O, S or a heteroatom such as Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in a single ring or a combination of two or more rings. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

In the present invention, “heteroaryl” means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon, preferably 1 to 3 carbons in the ring is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and furthermore, a form condensed with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl and the like, but are not limited thereto.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms. Such alkyloxy may include a linear, branched or cyclic structure. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means an aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” refers to silyl substituted with aryl having 6 to 60 carbon atoms.

In the present invention, “alkyl boron” refers to boron substituted with alkyl having 1 to 40 carbon atoms, and “aryl boron” refers to boron substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "arylphosphine" means a phosphine substituted with aryl having 6 to 60 carbon atoms, and "arylphosphine oxide group" means that phosphine substituted with aryl having 6 to 60 carbon atoms includes O do.

In the present invention, "condensed ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

In the present invention, “arylamine” means an amine substituted with an aryl having 6 to 60 carbon atoms.

The compound represented by Chemical Formula 1 of the present invention can be variously synthesized by referring to the synthesis process in the following examples.

2. Organic electroluminescent device

The present invention provides an organic electroluminescent device including the compound represented by Formula 1 above.

More specifically, the organic electroluminescent device according to the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers. includes the compound represented by Formula 1 above. At this time, the above compounds may be used alone or in combination of two or more.

The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and an electron injection layer, and at least one organic material layer among them may contain the compound represented by Formula 1 above. there is. Specifically, the organic material layer containing the compound of Chemical Formula 1 is preferably a light emitting layer.

The light emitting layer of the organic electroluminescent device of the present invention may include a host material (preferably, a phosphorescent host material). In addition, the light emitting layer of the organic electroluminescent device of the present invention may include a compound other than the compound of Formula 1 as a host.

The structure of the organic EL device of the present invention is not particularly limited, but a non-limiting example may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. . In this case, at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include the compound represented by Formula 1, and preferably the light emitting layer is represented by Formula 1 compounds may be included. Here, an electron injection layer may be additionally stacked on the electron transport layer. In addition, the structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.

On the other hand, the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode with materials and methods known in the art, except that at least one layer of the organic material layer contains the compound represented by Formula 1. there is.

The organic layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution application method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, but silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, and the like can be used.

*284 Further, as the anode material, metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole or polyaniline; and carbon black, but is not limited thereto.

In addition, as the negative electrode material, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; and multi-layered materials such as LiF/Al or LiO2/Al, but are not limited thereto.

In addition, the hole injection layer, the hole transport layer, the electron injection layer, and the electron transport layer are not particularly limited, and conventional materials known in the art may be used.

Hereinafter, the present invention will be described in detail through examples. However, the following examples are only to illustrate the present invention, and the present invention is not limited by the following examples.

[Preparation Example 1] Synthesis of Core-1

<Step 1> Synthesis of 2',6'-dibromo-5-chloro-2-methoxy-1,1'-biphenyl

(5-chloro-2-methoxyphenyl)boronic acid (186 g, 1,000 mmol) and 1,3-dibromo-2-iodobenzene (361 g, 1,000 mmol), Pd(PPh ₃ ) ₄ (46 g, 40 mmol) and KOH (168 g, 3,000 mmol) was added to 2 L of toluene and 1 L of H ₂ O and stirred at 110 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound, 2',6'-dibromo-5-chloro-2-methoxy-1,1'-biphenyl (316 g, yield 84%).

^1H -NMR: δ 3.83 (s, 3H), 6.91 (t, 1H), 6.99 (d, 1H), 7.34 (d, 2H), 7.60 (d, 2H), 7.90 (s, 1H)

<Step 2> Synthesis of 2',6'-dibromo-5-chloro-[1,1'-biphenyl]-2-ol

2',6'-dibromo-5-chloro-2-methoxy-1,1'-biphenyl (316 g, 840 mmol) and pyridine hydrochloride (485 g, 4,200 mmol) were mixed and stirred at 150 °C for 12 hours. . After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound, 2',6'-dibromo-5-chloro-[1,1'-biphenyl]-2-ol (290 g, yield 95%) was obtained by column chromatography. got it

^1H -NMR: δ 5.35 (s, 1H), 6.91 (t, 1H), 7.60 (d, 2H), 7.84 (s, 1H), 7.85 (d, 2H)

<Step 3> Synthesis of 1-bromo-8-chlorodibenzo[b,d]furan

2',6'-dibromo-5-chloro-[1,1'-biphenyl]-2-ol (290 g, 800 mmol) and sodium hydrosulfite (209 g, 1,200 mmol), KOH (67 g, 1,200 mmol) and tetrabutylammonium bromide (258 g, 800 mmol) were added to 1.6 L of DMF and stirred at 140°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound, 1-bromo-8-chlorodibenzo[b,d]furan (197 g, yield 88%).

^1H -NMR: δ 7.20 (d, 1H), 7.27 (t, 1H), 7.30 (d, 1H), 7.50 (s, 1H), 7.60 (d, 2H)

<Step 4> Synthesis of 3-(8-chlorodibenzo[b,d]furan-1-yl)-9-phenyl-9H-carbazole

(9-phenyl-9H-carbazol-3-yl)boronic acid (100 g, 350 mmol) and 1-bromo-8-chlorodibenzo[b,d]furan (99 g, 350 mmol) and Pd(PPh ₃ ) ₄ (16 g, 14 mmol) and NaOH (42 g, 1,050 mmol) were added to 700 ml of toluene and 350 ml of H ₂ O and stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and then recrystallized to obtain the target compound, 3-(8-chlorodibenzo[b,d]furan-1-yl)-9-phenyl-9H-carbazole (116 g, yield 75%) got

^1H -NMR: δ 7.20 (d, 1H), 7.25 (d, 1H), 7.33 (t, 1H), 7.44 (t, 1H), 7.45 (m, 1H), 7.50 (m, 3H), 7.58 ( m, 2H), 7.60 (d, 1H), 7.62 (d, 1H), 7.69 (d, 1H), 7.75 (d, 1H), 7.77 (s, 1H), 7.87 (d, 1H), 7.94 (d , 1H), 8.55 (d, 1H)

<Step 5> Synthesis of Core-1

3-(8-chlorodibenzo[b,d]furan-1-yl)-9-phenyl-9H-carbazole (116 g, 262 mmol) and Pd(dppf)Cl ₂ (8 g, 11 mmol), potassium acetate ( 77 g, 786 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (73 g, 288 mmol ) into DMF 500 ml and stirred at 110 ° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound Core-1 (120 g, yield 86%) was obtained by column chromatography.

^1H -NMR: δ 1.24 (s, 12H), 7.25 (m, 1H), 7.33 (m, 1H), 7.44 (m, 1H), 7.45 (m, 1H), 7.50 (m, 3H), 7.58 ( d, 1H), 7.62 (d, 1H), 7.66 (d, 1H), 7.69 (d, 1H), 7.75 (d, 1H), 7.77 (s, 1H), 7.80 (s, 1H), 7.87 (d , 1H), 7.94 (d, 1H), 8.55 (d, 1H)

[Preparation Example 2] Synthesis of Core-2

<Step 1> Synthesis of 9-([1,1'-biphenyl]-4-yl)-3-(8-chlorodibenzo[b,d]furan-1-yl)-9H-carbazole

(9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (127 g, 350 mmol) and 1-bromo-8-chlorodibenzo[b,d]furan ( 99 g, 350 mmol), Pd(PPh ₃ ) ₄ (16 g, 14 mmol), and NaOH (42 g, 1,050 mmol) were added to 700 ml of toluene and 350 ml of H ₂ O, and stirred at 110 °C for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and then recrystallized to obtain the target compound, 9-([1,1'-biphenyl]-4-yl)-3-(8-chlorodibenzo[b,d]furan-1-yl )-9H-carbazole (150 g, yield 82%) was obtained.

^1H -NMR: δ 7.20 (d, 1H), 7.25 (d, 1H), 7.33 (t, 1H), 7.44 (t, 1H), 7.45 (m, 1H), 7.50 (m, 3H), 7.58 ( m, 2H), 7.60 (d, 1H), 7.62 (d, 1H), 7.69 (d, 1H), 7.75 (d, 1H), 7.77 (s, 1H), 7.87 (d, 1H), 7.94 (d , 1H), 8.55 (d, 1H)

<Step 2> Synthesis of Core-2

9-([1,1'-biphenyl]-4-yl)-3-(8-chlorodibenzo[b,d]furan-1-yl)-9H-carbazole (52 g, 100 mmol) and Pd(dppf) Cl ₂ (2.9 g, 4 mmol), potassium acetate (29 g, 300 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1 ,3,2-dioxaborolane) (28 g, 110 mmol) was added to 200 ml of DMF and stirred at 110°C for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound Core-2 (50 g, yield 82%) was obtained by column chromatography.

^1H -NMR: δ 1.24 (s, 12H), 7.25 (m, 1H), 7.33 (m, 1H), 7.44 (m, 1H), 7.45 (m, 1H), 7.50 (m, 3H), 7.58 ( d, 1H), 7.62 (d, 1H), 7.66 (d, 1H), 7.68 (d, 2H), 7.69 (d, 1H), 7.75 (d, 1H), 7.77 (s, 1H), 7.79 (d , 2H), 7.80 (s, 1H), 7.87 (d, 1H), 7.94 (d, 1H), 8.55 (d, 1H)

[Preparation Example 3] Synthesis of Core-3

<Step 1> Synthesis of 3-bromo-2,5'-dichloro-2'-methoxy-1,1'-biphenyl

(5-chloro-2-methoxyphenyl)boronic acid (186 g, 1,000 mmol) and 1,3-dibromo-2-chlorobenzene (270 g, 1,000 mmol), Pd(PPh ₃ ) ₄ (46 g, 40 mmol) and KOH (168 g, 3,000 mmol) was added to 2 L of toluene and 1 L of H ₂ O and stirred at 110 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound, 3-bromo-2,5'-dichloro-2'-methoxy-1,1'-biphenyl (2796 g, yield 84%).

^1H -NMR: δ 3.83 (s, 3H), 6.99 (d, 1H), 7.28 (d, 1H), 7.34 (d, 1H), 7.50 (d, 1H), 7.67 (d, 1H), 7.90 ( s, 1H)

<Step 2> Synthesis of 3'-bromo-2',5-dichloro-[1,1'-biphenyl]-2-ol

3-bromo-2,5'-dichloro-2'-methoxy-1,1'-biphenyl (279 g, 840 mmol) and pyridine hydrochloride (485 g, 4,200 mmol) were mixed and stirred at 150 ° C for 12 hours. . After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound, 3'-bromo-2',5-dichloro-[1,1'-biphenyl]-2-ol (280 g, yield 84%) was obtained by column chromatography. got it

^1H -NMR: δ 5.35 (s, 1H), 7.28 (t, 1H), 7.50 (d, 1H), 7.67 (d, 1H), 7.84 (s, 1H), 7.85 (d, 2H)

<Step 3> Synthesis of 6-bromo-2-chlorodibenzo[b,d]furan

3'-bromo-2',5-dichloro-[1,1'-biphenyl]-2-ol (280 g, 800 mmol) and sodium hydrosulfite (209 g, 1,200 mmol), KOH (67 g, 1,200 mmol) and tetrabutylammonium bromide (258 g, 800 mmol) were added to 1.6 L of DMF and stirred at 140°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound, 6-bromo-2-chlorodibenzo[b,d]furan (200 g, yield 89%).

^1H -NMR: δ 7.20 (d, 1H), 7.21 (t, 1H), 7.36 (d, 1H), 7.50 (s, 1H), 7.60 (d, 1H), 7.83 (d, 1H)

<Step 4> Synthesis of 3-(8-chlorodibenzo[b,d]furan-4-yl)-9-phenyl-9H-carbazole

(9-phenyl-9H-carbazol-3-yl)boronic acid (100 g, 350 mmol) and 6-bromo-2-chlorodibenzo[b,d]furan (100 g, 350 mmol) and Pd(PPh ₃ ) ₄ (16 g, 14 mmol) and NaOH (42 g, 1,050 mmol) were added to 700 ml of toluene and 350 ml of H ₂ O and stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and then recrystallized to obtain the target compound, 3-(8-chlorodibenzo[b,d]furan-4-yl)-9-phenyl-9H-carbazole (118 g, yield 76%) got

^1H -NMR: δ 7.20 (d, 1H), 7.25 (d, 1H), 7.33 (t, 1H), 7.38 (t, 1H), 7.45 (m, 1H), 7.50 (m, 3H), 7.58 ( m, 2H), 7.60 (d, 1H), 7.69 (d, 1H), 7.77 (s, 1H), 7.81 (d, 1H), 7.85 (d, 1H), 7.87 (d, 1H), 7.94 (d , 1H), 8.55 (d, 1H)

<Step 5> Synthesis of Core-3

3-(8-chlorodibenzo[b,d]furan-4-yl)-9-phenyl-9H-carbazole (118 g, 266 mmol) and Pd(dppf)Cl ₂ (7.8 g, 11 mmol) potassium acetate (78 g, 798 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (74 g, 293 mmol) into 200 ml of DMF and stirred at 110 °C for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound Core-3 (120 g, yield 85%) was obtained by column chromatography.

^1H -NMR: δ 1.24 (s, 12H), 7.25 (m, 1H), 7.33 (m, 1H), 7.38 (m, 1H), 7.45 (m, 1H), 7.50 (m, 3H), 7.58 ( d, 1H), 7.66 (d, 1H), 7.69 (d, 1H), 7.77 (s, 1H), 7.80 (s, 1H), 7.81 (d, 1H), 7.85 (d, 1H), 7.87 (d , 1H), 7.94 (d, 1H), 8.55 (d, 1H)

[Preparation Example 4] Synthesis of Core-4

<Step 1> Synthesis of 9-([1,1'-biphenyl]-3-yl)-3-(8-chlorodibenzo[b,d]furan-4-yl)-9H-carbazole

(9-([1,1'-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid (128 g, 350 mmol) and 1-bromo-8-chlorodibenzo[b,d]furan ( 100 g, 350 mmol), Pd(PPh ₃ ) ₄ (16 g, 14 mmol), and NaOH (42 g, 1,050 mmol) were added to 700 ml of toluene and 350 ml of H ₂ O, followed by stirring at 110 °C for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, 9-([1,1'-biphenyl]-3-yl)-3-(8-chlorodibenzo[b,d]furan-4-yl )-9H-carbazole (120 g, yield 66%) was obtained.

^1H -NMR: δ 7.20 (d, 1H), 7.25 (d, 1H), 7.33 (t, 1H), 7.38 (m, 1H), 7.41 (t, 1H), 7.50 (m, 3H), 7.52 ( m, 2H), 7.60 (d, 1H), 7.69 (d, 1H), 7.77 (s, 1H), 7.81 (d, 1H), 7.85 (d, 1H), 7.87 (d, 1H), 7.94 (d , 1H), 8.55 (d, 1H)

<Step 2> Synthesis of Core-4

9-([1,1'-biphenyl]-3-yl)-3-(8-chlorodibenzo[b,d]furan-4-yl)-9H-carbazole (52 g, 100 mmol) and Pd(dppf) Cl ₂ (2.9 g, 4 mmol), potassium acetate (29 g, 300 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1 ,3,2-dioxaborolane) (28 g, 110 mmol) was added to 200 ml of DMF and stirred at 110°C for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound Core-4 (51 g, yield 84%) was obtained by column chromatography.

^1H -NMR: δ 1.25 (s, 12H), 7.25 (d, 1H), 7.33 (t, 1H), 7.38 (m 1H), 7.41 (t, 1H), 7.50 (m, 3H), 7.52 (m , 2H), 7.66 (d, 1H), 7.69 (d, 1H), 7.77 (d, 1H), 7.80 (d, 1H), 7.81 (d, 1H), 7.85 (d, 1H), 7.87 (d, 1H), 7.94 (d, 1H), 8.55 (d, 1H)

[Preparation Example 5] Synthesis of Core-5

<Step 1> Synthesis of 4-bromo-2,5'-dichloro-2'-methoxy-1,1'-biphenyl

(5-chloro-2-methoxyphenyl)boronic acid (186 g, 1,000 mmol) and 4-bromo-2-chloro-1-iodobenzene (317 g, 1,000 mmol), Pd(PPh ₃ ) ₄ (46 g, 40 mmol) ) and KOH (168 g, 3,000 mmol) were added to 2 L of toluene and 1 L of H ₂ O and stirred at 110 °C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound, 4-bromo-2,5'-dichloro-2'-methoxy-1,1'-biphenyl (227 g, yield 68%).

^1H -NMR: δ 3.83 (s, 3H), 6.99 (d, 1H), 7.34 (d, 1H), 7.54 (d, 1H), 7.62 (d, 1H), 7.88 (s, 1H), 7.90 ( s, 1H)

<Step 2> Synthesis of 4'-bromo-2',5-dichloro-[1,1'-biphenyl]-2-ol

4-bromo-2,5'-dichloro-2'-methoxy-1,1'-biphenyl (227 g, 683 mmol) and pyridine hydrochloride (395 g, 3,419 mmol) were mixed and stirred at 150 ° C for 12 hours. . After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound, 4'-bromo-2',5-dichloro-[1,1'-biphenyl]-2-ol (185 g, yield 85%) was obtained by column chromatography. got it

^1H -NMR: δ 5.35 (s, 1H), 7.54 (t, 1H), 7.62 (d, 1H), 7.84 (s, 1H), 7.85 (d, 2H), 7.88 (s, 1H)

<Step 3> Synthesis of 7-bromo-2-chlorodibenzo[b,d]furan

4'-bromo-2',5-dichloro-[1,1'-biphenyl]-2-ol (185 g, 582 mmol) and sodium hydrosulfite (138 g, 792 mmol), KOH (44 g, 792 mmol) and tetrabutylammonium bromide (170 g, 528 mmol) were added to 900 ml of DMF and stirred at 140°C for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was used to obtain the target compound, 7-bromo-2-chlorodibenzo[b,d]furan (164 g, yield 82%).

^1H -NMR: δ 7.20 (d, 1H), 7.30 (d, 1H), 7.50 (s, 1H), 7.60 (d, 1H), 7.78 (d, 1H), 8.26 (s, 1H)

<Step 4> Synthesis of 3-(8-chlorodibenzo[b,d]furan-3-yl)-9-phenyl-9H-carbazole

(9-phenyl-9H-carbazol-3-yl)boronic acid (100 g, 350 mmol) and 7-bromo-2-chlorodibenzo[b,d]furan (100 g, 350 mmol) and Pd(PPh ₃ ) ₄ (16 g, 14 mmol) and NaOH (42 g, 1,050 mmol) were added to 700 ml of toluene and 350 ml of H ₂ O and stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, 3-(8-chlorodibenzo[b,d]furan-3-yl)-9-phenyl-9H-carbazole (120 g, yield 77%) got

^1H -NMR: δ 7.20 (d, 1H), 7.25 (d, 1H), 7.33 (t, 1H), 7.45 (m, 1H), 7.50 (m, 3H), 7.58 (m, 2H), 7.60 ( d, 1H), 7.69 (d, 1H), 7.64 (s, 1H), 7.75 (d, 1H), 7.77 (s, 1H), 7.87 (d, 1H), 7.94 (d, 1H), 7.95 (d , 1H), 8.55 (d, 1H)

<Step 5> Synthesis of Core-5

3-(8-chlorodibenzo[b,d]furan-3-yl)-9-phenyl-9H-carbazole (120 g, 270 mmol) and Pd(dppf)Cl ₂ (7.9 g, 11 mmol), potassium acetate ( 79 g, 806 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (82 g, 323 mmol) ) into DMF 500 ml and stirred at 110 ° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound Core-5 (115 g, yield 80%) was obtained by column chromatography.

^1H -NMR: δ 1.24 (s, 12H), 7.25 (m, 1H), 7.33 (m, 1H), 7.45 (m, 1H), 7.50 (m, 3H), 7.58 (d, 1H), 7.64 ( s, 1H), 7.66 (d, 1H), 7.69 (d, 1H), 7.75 (d, 1H), 7.77 (s, 1H), 7.80 (s, 1H), 7.87 (d, 1H), 7.94 (d , 1H), 7.95 (d, 1H), 8.55 (d, 1H)

[Preparation Example 6] Synthesis of Core-6

<Step 1> Synthesis of 9-([1,1'-biphenyl]-2-yl)-3-(8-chlorodibenzo[b,d]furan-4-yl)-9H-carbazole

(9-([1,1'-biphenyl]-2-yl)-9H-carbazol-3-yl)boronic acid (36 g, 100 mmol) and 7-bromo-2-chlorodibenzo[b,d]furan ( 28 g, 100 mmol), Pd(PPh ₃ ) ₄ (4.6 g, 4 mmol), and NaOH (12 g, 300 mmol) were added to 200 ml of toluene and 100 ml of H ₂ O, and the mixture was stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, 9-([1,1'-biphenyl]-2-yl)-3-(8-chlorodibenzo[b,d]furan-4-yl )-9H-carbazole (45 g, yield 87%) was obtained.

^1H -NMR: 7.19 (d, 2H), 7.25 (d, 1H), 7.33 (t, 1H), 7.45 (m, 1H), 7.50 (m, 4H), 7.54 (m, 1H), 7.64 (s , 1H), 7.66 (d, 1H), 7.68 (d, 1H), 7.69 (d, 1H), 7.75 (d, 1H), 7.77 (s, 1H), 7.79 (d, 1H), 7.80 (s, 1H), 7.87 (d, 1H), 7.94 (d, 1H), 7.95 (d, 1H), 8.55 (d, 1H)

<Step 2> Synthesis of Core-6

9-([1,1'-biphenyl]-2-yl)-3-(8-chlorodibenzo[b,d]furan-4-yl)-9H-carbazole (45 g, 87 mmol) and Pd(dppf) Cl ₂ (2.5 g, 3mmol), potassium acetate (25 g, 260 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1, 3,2-dioxaborolane) (24 g, 93 mmol) was added to 180 ml of DMF and stirred at 110°C for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound Core-6 (45 g, yield 85%) was obtained by column chromatography.

^1H -NMR: δ 1.24 (s, 12H), 7.19 (d, 2H), 7.20 (d, 1H), 7.25 (d, 1H), 7.33 (t, 1H), 7.45 (m, 1H), 7.50 ( m, 4H), 7.54 (m, 1H), 7.60 (d, 1H), 7.64 (s, 1H), 7.68 (d, 1H), 7.69 (d, 1H), 7.75 (d, 1H), 7.77 (s) , 1H), 7.79 (d, 1H), 7.87 (d, 1H), 7.94 (d, 1H), 7.95 (d, 1H), 8.55 (d, 1H)

[Preparation Example 7] Synthesis of Core-7

<Step 1> Synthesis of 2-chloro-7-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan

(9,9-dimethyl-9H-fluoren-2-yl)boronic acid (24 g, 100 mmol) and 7-bromo-2-chlorodibenzo[b,d]furan (28 g, 100 mmol) and Pd (PPh ₃ ) ₄ (4.6 g, 4 mmol) and NaOH (12 g, 300 mmol) were added to 200 ml of toluene and 100 ml of H ₂ O and stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and then recrystallized to obtain the target compound, 2-chloro-7-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan (28 g, yield 72%) was obtained.

^1H -NMR: δ 1.72 (s, 6H), 7.20 (d, 1H), 7.28 (t, 1H), 7.38 (t, 1H), 7.50 (s, 1H), 7.55 (d, 1H), 7.60 ( d, 1H), 7.63 (d, 1H), 7.64 (s, 1H), 7.75 (d, 1H), 7.77 (s, 1H), 7.87 (d, 1H), 7.93 (d, 1H), 7.95 (d , 1H)

<Step 2> Synthesis of Core-7

2-chloro-7-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan (28 g, 71 mmol) and Pd(dppf)Cl ₂ (2 g, 3 mmol), potassium acetate (21 g, 213 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (22 g , 85 mmol) was added to 200 ml of DMF and stirred at 110° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound Core-7 (25 g, yield 71%) was obtained by column chromatography.

^1H -NMR: δ 1.24 (s, 12H), 1.72 (s, 6H), 7.28 (t, 1H), 7.38 (t, 1H), 7.50 (d, 1H), 7.55 (d, 1H), 7.63 ( d, 1H), 7.64 (s, 1H), 7.66 (d, 1H), 7.75 (d, 1H), 7.77 (s, 1H), 7.80 (s, 1H), 7.87 (d, 1H), 7.93 (d , 1H), 7.95 (d, 1H)

[Preparation Example 8] Synthesis of Core-8

<Step 1> Synthesis of 9-([1,1'-biphenyl]-4-yl)-3-(8-chlorodibenzo[b,d]furan-4-yl)-9H-carbazole

(9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl)boronic acid (18 g, 50 mmol) and 7-bromo-2-chlorodibenzo[b,d]furan ( 14 g, 50 mmol), Pd(PPh ₃ ) ₄ (2.3 g, 2 mmol), and NaOH (6 g, 150 mmol) were added to 100 ml of toluene and 50 ml of H ₂ O, and the mixture was stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and then recrystallized to obtain the target compound, 9-([1,1'-biphenyl]-4-yl)-3-(8-chlorodibenzo[b,d]furan-4-yl )-9H-carbazole (23 g, yield 87%) was obtained.

^1H -NMR: 7.20 (d, 1H), 7.25 (t, 1H), 7.33 (t, 1H), 7.41 (m, 1H), 7.50 (s, 1H), 7.51 (m, 2H), 7.52 (d , 2H), 7.60 (d, 1H), 7.64 (s, 1H), 7.68 (d, 2H), 7.69 (d, 1H), 7.75 (d, 1H), 7.77 (s, 1H), 7.79 (d, 2H), 7.87 (d, 1H), 7.94 (d, 1H), 7.95 (d, 1H), 8.55 (d, 1H)

<Step 2> Synthesis of Core-8

9-([1,1'-biphenyl]-4-yl)-3-(8-chlorodibenzo[b,d]furan-4-yl)-9H-carbazole (23 g, 44 mmol) and Pd(dppf) Cl ₂ (1.3 g, 1.8 mmol), potassium acetate (13 g, 132 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1 ,3,2-dioxaborolane) (12 g, 53 mmol) was added to 180 ml of DMF and stirred at 110°C for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound Core-8 (23 g, yield 85%) was obtained by column chromatography.

^1H -NMR: 1.24 (s, 12H), 7.25 (t, 1H), 7.33 (t, 1H), 7.41 (m, 1H), 7.50 (m, 2H), 7.51 (m, 2H), 7.52 (d , 2H), 7.60 (d, 1H), 7.64 (s, 1H), 7.66 (d, 1H), 7.68 (d, 2H), 7.69 (d, 1H), 7.75 (d, 1H), 7.77 (s, 1H), 7.79 (d, 2H), 7.80 (s, 1H), 7.87 (d, 1H), 7.94 (d, 1H), 7.95 (d, 1H), 8.55 (d, 1H)

[Preparation Example 9] Synthesis of Core-9

<Step 1> Synthesis of 3-(8-chlorodibenzo[b,d]furan-2-yl)-9-phenyl-9H-carbazole

(9-phenyl-9H-carbazol-3-yl)boronic acid (100 g, 350 mmol) and 2-bromo-8-chlorodibenzo[b,d]furan (100 g, 350 mmol) and Pd(PPh ₃ ) ₄ (16 g, 14 mmol) and NaOH (42 g, 1,050 mmol) were added to 700 ml of toluene and 350 ml of H ₂ O and stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, 3-(8-chlorodibenzo[b,d]furan-2-yl)-9-phenyl-9H-carbazole (132 g, yield 85%) got

^1H -NMR: δ 7.20 (d, 1H), 7.25 (d, 1H), 7.33 (d, 1H), 7.45 (m, 1H), 7.50 (m, 3H), 7.58 (t, 2H), 7.60 ( d, 1H), 7.69 (d, 1H), 7.71 (s, 1H), 7.72 (d, 1H), 7.77 (s, 1H), 7.81 (d, 1H), 7.87 (d, 1H), 7.94 (d , 1H), 8.55 (d, 1H)

<Step 2> Synthesis of Core-9

3-(8-chlorodibenzo[b,d]furan-2-yl)-9-phenyl-9H-carbazole (132 g, 298 mmol) and Pd(dppf)Cl ₂ (9 g, 12 mmol), potassium acetate ( 88 g, 894 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (91 g, 358 mmol) ) into DMF 200 ml and stirred at 110 ° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound Core-9 (138 g, yield 87%) was obtained by column chromatography.

^1H -NMR: δ 1.24 (s, 12H), 7.25 (d, 1H), 7.33 (d, 1H), 7.45 (m, 1H), 7.50 (m, 3H), 7.58 (t, 2H), 7.66 ( d, 1H), 7.69 (d, 1H), 7.71 (s, 1H), 7.72 (d, 1H), 7.77 (s, 1H), 7.80 (s, 1H), 7.81 (d, 1H), 7.87 (d , 1H), 7.94 (d, 1H), 8.55 (d, 1H)

[Preparation Example 10] Synthesis of Core-10

<Step 1> Synthesis of 9-([1,1'-biphenyl]-2-yl)-3-(8-chlorodibenzo[b,d]furan-2-yl)-9H-carbazole

(9-([1,1'-biphenyl]-2-yl)-9H-carbazol-3-yl)boronic acid (36 g, 100 mmol) and 2-bromo-8-chlorodibenzo[b,d]furan ( 28 g, 100 mmol), Pd(PPh ₃ ) ₄ (4.6 g, 4 mmol), and NaOH (12 g, 300 mmol) were added to 200 ml of toluene and 100 ml of H ₂ O, and the mixture was stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, 9-([1,1'-biphenyl]-2-yl)-3-(8-chlorodibenzo[b,d]furan-2-yl )-9H-carbazole (39 g, yield 75%) was obtained.

^1H -NMR: 7.19 (d, 2H), 7.20, (d, 1H), 7.25 (d, 1H), 7.33 (t, 1H), 7.45 (m, 1H), 7.50 (m, 4H), 7.54 ( m, 1H), 7.60 (d, 1H), 7.68 (d, 1H), 7.69 (d, 1H), 7.71 (s, 1H), 7.72 (d, 1H), 7.77 (s, 1H), 7.79(d) , 1H), 7.81 (d, 1H), 7.87 (d, 1H), 7.94 (d, 1H), 8.55 (d, 1H)

<Step 2> Synthesis of Core-10

9-([1,1'-biphenyl]-2-yl)-3-(8-chlorodibenzo[b,d]furan-2-yl)-9H-carbazole (39 g, 76 mmol) and Pd(dppf) Cl ₂ (2.2 g, 3mmol), potassium acetate (22 g, 226 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1, 3,2-dioxaborolane) (21 g, 81 mmol) was added to 150 ml of DMF and stirred at 110 °C for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound Core-10 (39 g, yield 85%) was obtained by column chromatography.

^1H -NMR: 1.24 (s, 12H), 7.19 (d, 2H), 7.25 (d, 1H), 7.33 (t, 1H), 7.45 (m, 1H), 7.50 (m, 4H), 7.54 (m , 1H), 7.68 (d, 1H), 7.66 (d, 1H), 7.69 (d, 1H), 7.71 (s, 1H), 7.72 (d, 1H), 7.77 (s, 1H), 7.79 (d, 1H), 7.80 (s, 1H), 7.81 (d, 1H), 7.87 (d, 1H), 7.94 (d, 1H), 8.55 (d, 1H)

[Preparation Example 11] Synthesis of Core-11

<Step 1> Synthesis of 3-(8-chlorodibenzo[b,d]thiophen-2-yl)-9-phenyl-9H-carbazole

(9-phenyl-9H-carbazol-3-yl)boronic acid (29 g, 100 mmol) and 2-bromo-8-chlorodibenzo[b,d]thiophene (30 g, 100 mmol) and Pd(PPh ₃ ) ₄ (4.6 g, 4 mmol) and NaOH (12 g, 300 mmol) were added to 200 ml of toluene and 100 ml of H ₂ O, and the mixture was stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, 3-(8-chlorodibenzo[b,d]thiophen-2-yl)-9-phenyl-9H-carbazole (35 g, yield 76%) got

^1H -NMR: δ 7.25 (d, 1H), 7.33 (d, 1H), 7.45 (m, 1H), 7.48 (d, 1H), 7.50 (m, 2H), 7.58 (t, 2H), 7.69 ( d, 1H), 7.77 (s, 1H), 7.86 (d, 1H), 7.87 (d, 1H), 7.92 (d, 1H), 7.94 (d, 1H), 8.00 (m, 2H), 8.24 (s) , 1H), 8.55 (d, 1H)

<Step 2> Synthesis of Core-11

3-(8-chlorodibenzo[b,d]thiophen-2-yl)-9-phenyl-9H-carbazole (35 g, 76 mmol) and Pd(dppf)Cl ₂ (2.2 g, 3 mmol), potassium acetate ( 22 g, 228 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (23 g, 91 mmol) ) into DMF 200 ml and stirred at 110 ° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO ₄ was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, the target compound Core-11 (30 g, yield 71%) was obtained by column chromatography.

^1H -NMR: δ 7.25 (d, 1H), 7.33 (d, 1H), 7.45 (m, 1H), 7.47 (d, 1H), 7.50 (m, 2H), 7.58 (t, 2H), 7.69 ( d, 1H), 7.77 (s, 1H), 7.86 (d, 1H), 7.87 (d, 1H), 7.94 (m, 2H), 7.98 (d, 1H), 8.00 (m, 2H), 8.55 (d , 1H)

[Synthesis Example 1] Synthesis of Compound A-1

Core-1 (5.4 g, 10.0 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2.7 g, 10.0 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) was added to 20 ml of toluene and 10 ml of H ₂ O, and the mixture was stirred at 110 °C for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, Compound A-1 (5.4 g, yield 85%).

[LCMS]: 640

[Synthesis Example 2] Synthesis of Compound A-2

Core-2 (6.1 g, 10.0 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2.7 g, 10.0 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) was added to 20 ml of toluene and 10 ml of H ₂ O, and the mixture was stirred at 110 °C for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and then recrystallized to obtain the target compound, Compound A-2 (5.9 g, yield 83%).

[LCMS]: 716

[Synthesis Example 3] Synthesis of Compound B-1

Core-1 (5.4 g, 10.0 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.5 g, 10.0 mmol) And Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) and NaOH (1.2 g, 30.0 mmol) were added to 20 ml of toluene and 10 ml of H ₂ O, and the mixture was stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, Compound B-1 (5.3 g, yield 74%).

[LCMS]: 716

*449

[Synthesis Example 4] Synthesis of Compound C-2

Core-1 (5.4 g, 10.0 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (3.6 g, 10.0 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) and NaOH (1.2 g, 30.0 mmol) were added to 20 ml of toluene and 10 ml of H ₂ O, and the mixture was stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, Compound C-2 (6.4 g, yield 88%).

[LCMS]: 730

[Synthesis Example 5] Synthesis of Compound C-5

Core-1 (5.4 g, 10.0 mmol) and 2-chloro-4-(9,9-dimethyl-9H-fluoren-2-yl)-6-phenyl-1,3,5-triazine (3.8 g, 10.0 mmol) ) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) and NaOH (1.2 g, 30.0 mmol) were added to 20 ml of toluene and 10 ml of H ₂ O and stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, Compound C-5 (5.9 g, yield 77%).

[LCMS]: 756

[Synthesis Example 6] Synthesis of Compound D-1

Core-3 (5.4 g, 10.0 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2.7 g, 10.0 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) was added to 20 ml of toluene and 10 ml of H ₂ O, and the mixture was stirred at 110 °C for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, Compound D-1 (4.4 g, yield 69%).

[LCMS]: 640

[Synthesis Example 7] Synthesis of Compound D-3

Core-4 (6.1 g, 10.0 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2.7 g, 10.0 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) was added to 20 ml of toluene and 10 ml of H ₂ O, and the mixture was stirred at 110 °C for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, Compound D-3 (6.1 g, yield 85%).

[LCMS]: 716

[Synthesis Example 8] Synthesis of Compound E-1

Core-3 (5.4 g, 10.0 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.4 g, 10.0 mmol) And Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) and NaOH (1.2 g, 30.0 mmol) were added to 20 ml of toluene and 10 ml of H ₂ O, and the mixture was stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, Compound E-1 (5.6 g, yield 78%).

[LCMS]: 716

[Synthesis Example 9] Synthesis of Compound E-47

Core-3 (5.4 g, 10.0 mmol) and 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (4.2 g, 10.0 mmol) Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) and NaOH (1.2 g, 30.0 mmol) were added to 20 ml of toluene and 10 ml of H ₂ O, and the mixture was stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, Compound E-47 (6.9 g, yield 87%).

[LCMS]: 792

[Synthesis Example 10] Synthesis of Compound F-4

Core-3 (5.4 g, 10.0 mmol) and 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (3.6 g, 10.0 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) and NaOH (1.2 g, 30.0 mmol) were added to 20 ml of toluene and 10 ml of H ₂ O, and the mixture was stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and then recrystallized to obtain the target compound, Compound F-4 (5.4 g, yield 74%).

[LCMS]: 730

[Synthesis Example 11] Synthesis of Compound G-1

Core-5 (5.4 g, 10.0 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2.7 g, 10.0 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) was added to 20 ml of toluene and 10 ml of H ₂ O, and the mixture was stirred at 110 °C for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and then recrystallized to obtain the target compound, Compound G-1 (4.9 g, yield 77%).

[LCMS]: 640

[Synthesis Example 12] Synthesis of Compound G-4

Core-6 (6.1 g, 10.0 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2.7 g, 10.0 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) was added to 20 ml of toluene and 10 ml of H ₂ O, and the mixture was stirred at 110 °C for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, Compound G-4 (6.3 g, yield 88%).

[LCMS]: 716

[Synthesis Example 13] Synthesis of Compound G-56

Core-7 (4.9 g, 10.0 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2.7 g, 10.0 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) was added to 20 ml of toluene and 10 ml of H ₂ O, and the mixture was stirred at 110 °C for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, Compound G-56 (4.3 g, yield 72%).

[LCMS]: 591

[Synthesis Example 14] Synthesis of Compound H-2

Core-8 (6.1 g, 10.0 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.4 g, 10.0 mmol) And Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) and NaOH (1.2 g, 30.0 mmol) were added to 20 ml of toluene and 10 ml of H ₂ O, and the mixture was stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, Compound H-2 (6.6 g, yield 83%).

[LCMS]: 792

[Synthesis Example 15] Synthesis of Compound H-32

Core-5 (5.4 g, 10.0 mmol) and 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.4 g, 10.0 mmol) And Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) and NaOH (1.2 g, 30.0 mmol) were added to 20 ml of toluene and 10 ml of H ₂ O, and the mixture was stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, Compound H-32 (6.2 g, yield 86%).

[LCMS]: 716

[Synthesis Example 16] Synthesis of Compound J-1

Core-9 (5.4 g, 10.0 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2.7 g, 10.0 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) was added to 20 ml of toluene and 10 ml of H ₂ O, and the mixture was stirred at 110 °C for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and then recrystallized to obtain the target compound, Compound J-1 (5.3 g, yield 82%).

[LCMS]: 640

[Synthesis Example 17] Synthesis of Compound J-4

Core-10 (6.1 g, 10.0 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2.7 g, 10.0 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol), NaOH (1.2 g, 30.0 mmol) was added to 40 ml of toluene and 20 ml of H ₂ O and stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, Compound J-4 (6.3 g, yield 87%).

[LCMS]: 716

[Synthesis Example 18] Synthesis of Compound K-1

Core-9 (5.4 g, 10.0 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.4 g, 10.0 mmol) And Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) and NaOH (1.2 g, 30.0 mmol) were added to 20 ml of toluene and 10 ml of H ₂ O, and the mixture was stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, Compound K-1 (6.3 g, yield 88%).

[LCMS]: 716

*524

[Synthesis Example 19] Synthesis of Compound L-37

Core-9 (5.4 g, 10.0 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(dibenzo[b,d]furan-3-yl)-1, 3,5-triazine (4.3 g, 10.0 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) and NaOH (1.2 g, 30.0 mmol) were added to 20 ml of toluene and 10 ml of H ₂ O and heated at 110 °C. Stir for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and then recrystallized to obtain the target compound, Compound K-37 (7.2 g, yield 89%).

[LCMS]: 806

[Synthesis Example 20] Synthesis of Compound L-51

Core-11 (5.5 g, 10.0 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (2.7 g, 10.0 mmol) and Pd(PPh ₃ ) ₄ (0.5 g, 0.4 mmol) and NaOH (1.2 g, 30.0 mmol) were added to 20 ml of toluene and 10 ml of H ₂ O, and the mixture was stirred at 110° C. for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered through silica, and recrystallized to obtain the target compound, Compound L-51 (5.7 g, yield 76%).

[LCMS]: 746

[Example 1 to 20] Fabrication of green organic electroluminescent device

Compounds A-1, A-2, B-1, C-2, C-5, D-1, D-3, E-1, E-37, F-4 synthesized in Synthesis Examples 1 to 20, G-1, G-4, G-56, H-2, H-32, J-1, J-4, K-1, L-37, and L-51 were sublimated to a high purity by a commonly known method. Afterwards, a green organic electroluminescent device was fabricated according to the following process.

First, a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, it is ultrasonically washed with solvents such as isopropyl alcohol, acetone, and methanol, dried, transferred to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and then cleaned by using UV for 5 minutes and vacuum evaporator The substrate was transferred to

On the prepared ITO transparent electrode, m-MTDATA (60 nm) / TCTA (80 nm) / 90% of the above synthetic example compound + 10% of Ir (ppy) ₃ (30 nm) / BCP (10 nm) / Alq ₃ ( 30 nm)/LiF (1 nm)/Al (200 nm) were laminated in this order to fabricate an organic electroluminescent device.

[Comparative Example 1] Production of green organic electroluminescent device

A green organic electroluminescent device was manufactured in the same manner as in Example 1, except for using CBP instead of Compound A-1 as a light emitting host material when forming the light emitting layer.

[Comparative Example 2] Production of green organic electroluminescent device

A green organic electroluminescent device was manufactured in the same manner as in Example 1, except for using Compound 1 instead of Compound A-1 as a light emitting host material when forming the light emitting layer.

[Comparative Example 3] Fabrication of green organic electroluminescent device

A green organic electroluminescent device was manufactured in the same manner as in Example 1, except for using Compound 2 instead of Compound A-1 as a light emitting host material when forming the light emitting layer.

The structures of m-MTDATA, TCTA, Ir(ppy) ₃ , CBP, BCP, and compounds 1 and 2 used in Examples 1 to 20 and Comparative Examples 1 to 3 are as follows.

[Evaluation Example 1]

For each of the green organic electroluminescent devices prepared in Examples 1 to 20 and Comparative Examples 1 to 3, driving voltage, current efficiency and emission peak at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below. showed up

Sample host drive voltage
(V) emission peak
(nm) current efficiency
(cd/A) Example 1 A-1 5.62 516 45.5 Example 2 A-2 5.55 516 46.5 Example 3 B-1 5.46 516 42.1 Example 4 C-2 5.33 516 43.0 Example 5 C-5 4.95 516 51.2 Example 6 D-1 5.01 516 53.1 Example 7 D-3 4.88 516 48.2 Example 8 E-1 4.58 516 40.2 Example 9 E-47 5.23 516 55.5 Example 10 F-4 4.76 516 42.1 Example 11 G-1 4.54 516 58.0 Example 12 G-4 4.99 516 52.7 Example 13 G-56 5.01 516 55.5 Example 14 H-2 4.21 516 56.3 Example 15 H-32 5.46 516 49.6 Example 16 J-1 4.87 516 47.2 Example 17 J-4 5.21 516 53.1 Example 18 K-1 4.77 516 62.1 Example 19 L-37 4.56 516 60.3 Example 20 L-51 4.99 516 47.7 Comparative Example 1 CBP 6.93 516 38.2 Comparative Example 2 One 5.67 516 42.1 Comparative Example 3 2 5.55 516 41.2

As shown in Table 1, when the compound according to the present invention is applied to the light emitting layer of the green organic light emitting device (Examples 1 to 20), conventional CBP and compounds 1 and 2 are applied to the light emitting layer of the green organic light emitting device. It was found that compared to the case (Comparative Examples 1 to 3), it exhibited better performance in terms of current efficiency and driving voltage.

Claims (10)

A compound represented by the following formula (1).
[Formula 1]

In Formula 1,
X is CR ₃ R ₄ ;
L is a single bond or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
Y is O or S;
Z ₁ to Z ₃ are N;
n is 0;
R ₁ , R ₃ to R ₅ , Ar ₁ and Ar ₂ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a halogen group, a cyano group, a C ₁ ~ C ₄₀ alkyl group, or a C ₂ ~ C ₄₀ alky It is selected from the group consisting of a yl group, a C ₂ ~ C ₄₀ alkynyl group, a C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, or they may form a condensed ring with an adjacent group,
Ar ₁ and Ar ₂ are hydrogen, deuterium, halogen group, cyano group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group. selected from the group consisting of, or they may form a condensed ring with an adjacent group,
The arylene group and the heteroarylene group of L, and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group of R ₁ , R ₃ to R ₅ , Ar ₁ and Ar ₂ group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl amine group are each independently deuterium, halogen, cyano group, nitro group, amino group, C ₂ ~C ₄₀ alkenyl group, C ₂ ~C ₄₀ alkynyl group, C ₃ ~C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ ~C ₄₀ alkyl group, C ₆ ~C Aryl group of ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group and C ₆ It is substituted or unsubstituted with one or more substituents selected from the group consisting of ~C ₆₀ arylamine groups, and when the substituents are plural, they are the same as or different from each other. According to claim 1,
The compound represented by Formula 1 is a compound represented by any one of Formulas 2 to 5 below.
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5,
X, L, Y, Z ₁ to Z ₃ , n, R ₁ , Ar ₁ and Ar ₂ are each as defined in claim 1. According to claim 1,
Wherein R ₃ and R ₄ are bonded to each other to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring. According to claim 1,
The compound represented by Formula 1 is a compound represented by any one of Formulas 8 to 14.
[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

In Formulas 8 to 14,
L, Y, Z ₁ to Z ₃ , n, R ₁ , Ar ₁ and Ar ₂ are each as defined in claim 1. According to claim 1,
Wherein Z ₁ to Z ₃ are all N compounds. According to claim 1,
Wherein R ₁ and R ₃ to R ₅ are the same as or different from each other, and are each independently hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, It is selected from the group consisting of a C ₆ ~ C ₆₀ aryloxy group, a C ₆ ~ C ₆₀ arylsilyl group, a C ₆ ~ C ₆₀ arylboron group, and a C ₆ ~ C ₆₀ arylamine group, or they are condensed with adjacent groups. A compound capable of forming a ring. According to claim 1,
Wherein Ar ₁ and Ar ₂ are substituents selected from the group consisting of the following structural formula:

In the above structural formula,
* means a site bonded to Formula 1. Including an anode, a cathode and one or more organic material layers interposed between the anode and the cathode,
An organic electroluminescent device in which at least one of the one or more organic material layers contains the compound according to any one of claims 1 to 7. According to claim 8,
An organic electroluminescent device wherein the organic material layer containing the compound is selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and an electron injection layer. According to claim 8,
The organic material layer containing the compound is a phosphorescent light emitting layer organic electroluminescent device.