KR102578497B1 - 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 specifically, to a novel compound with excellent luminescence performance and improved properties such as high luminous efficiency, low driving voltage, and long lifespan by including the same in one or more organic material layers. It relates to organic electroluminescent devices.

Description

Organic compounds and organic electroluminescent devices 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. More specifically, a compound with excellent luminous performance and an organic electroluminescent device with improved properties such as luminous efficiency, driving voltage, and lifespan by including the same in one or more organic material layers. It's about.

Beginning with Bernanose's observation of organic thin film luminescence in the 1950s, research on organic electroluminescent devices, which led to blue electroluminescence using anthracene single crystals in 1965, was divided into a functional layer of a hole layer and a light emitting layer by Tang in 1987. An organic electroluminescent device with a layered structure was presented. Since then, in order to create high-efficiency, long-life organic electroluminescent devices, there has been development in the form of introducing each characteristic organic material layer within the device, leading to the development of specialized materials used for this.

When a voltage is applied between two electrodes in an organic electroluminescent device, holes are injected from the anode and electrons are injected from the cathode into the organic material layer. When the injected hole and electron meet, an exciton is formed, and when this exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into light-emitting material, hole injection material, hole transport material, electron transport material, electron injection material, etc., depending on its function.

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

Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. The development of these phosphorescent materials can theoretically improve luminous efficiency by up to 4 times compared to fluorescence, so interest is focused on not only phosphorescent dopants but also phosphorescent host materials.

To date, NPB, BCP, and Alq ₃ are widely known as materials used for the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer, and as light-emitting materials, anthracene derivatives have been reported as fluorescent dopant/host materials. . In particular, among light emitting materials, phosphorescent materials that have great advantages in terms of improving efficiency include metal complex compounds containing Ir such as Firpic, Ir(ppy) ₃ , (acac)Ir(btp) _{2 ,} etc., which are used as blue, green, and red dopant materials. It is being used as. To date, CBP has shown excellent properties as a phosphorescent host material.

However, conventional light-emitting materials have advantages in terms of light-emitting properties, but because their glass transition temperature is low and thermal stability is very poor, they are not at a satisfactory level in terms of lifespan in organic electroluminescent devices. Therefore, there is a demand for the development of light-emitting materials with excellent performance.

Japanese Patent Publication No. 2001-160489

In order to solve the above problems, the present invention can be applied to organic electroluminescent devices and aims to provide a new organic compound with excellent luminescent performance by satisfying the required appropriate range of energy level, electrochemical stability, thermal stability, etc. Do it as

In addition, the present invention aims to provide an organic electroluminescent device containing the novel organic compound, which exhibits low driving voltage and high luminous efficiency, and has improved lifespan.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1).

Compound represented by Formula 1:

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 an arylene group of C ₆ to C ₁₈ and a heteroarylene group of 5 to 18 nuclear atoms,

Y is O or S,

Z ₁ to Z ₃ are the same 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 are each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, hetero group with 5 to 60 nuclear atoms 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 to C ₆₀ aryl boron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group, Alternatively, they may form condensed rings with adjacent groups,

The 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 The oxy group, alkyl silyl group, aryl silyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, and aryl amine group each independently contain 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 with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ aryl Silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ arylphosphine oxide group and C ₆ ~ C ₆₀ is 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 or different from each other.

In addition, the present invention provides an organic material comprising 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. An electroluminescent device is provided. Here, the organic material layer containing the compound represented by Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, an auxiliary light emitting layer, a light emitting layer, an electron transport layer, and an electron injection layer. At this time, the compound represented by Formula 1 may be used as a phosphorescent host of the light-emitting layer.

The compound represented by Formula 1 of the present invention has excellent thermal stability and luminescence properties, so it can be used as a material for the 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, it is possible to manufacture an organic electroluminescent device with low driving voltage, high efficiency, and long lifespan compared to conventional host materials, and further improves performance and lifespan. 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 one of positions 5 to 8 when an electron withdrawer is bonded to the 3 position of dibenzofuran (Y=O) or dibenzothiophene (Y=S). An electron pusher may be coupled to the position. The compound represented by Formula 1 may be embodied in any one of Formulas 2 to 5 below.

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 Formula 1 above.

In the compound represented by Formula 1, X is NR ₂ or CR ₃ R ₄ . _At this _{time , when}

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

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

Here, as the binding position of the electron pusher moves from position 5 to position 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 Formula 1 preferably has an electron withdrawing group bonded to the 5th position of dibenzofuran or dibenzothiophene (see Formula 2 above) so that it can exhibit an appropriate LUMO level as a green light-emitting layer material.

The electron withdrawing group may be carbazole, fluorene, condensed fluorene having a spiro structure, etc. At this time, it is preferable that the electron withdrawing group is carbazole with a large electron donating capacity.

The compound of Formula 1 containing such an electron withdrawing group may be specified as one of the following Formulas 6 to 14.

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

In the compound represented by Formula 1, Z ₁ to Z ₃ are the same or different from each other and are each independently N or CR ₅ , and at least one of them is N. More specifically, Z ₁ to Z ₃ contain one or more N, and the electron withdrawing group may be pyridine, pyrimidine, or triazine. At this time, it is preferable that it is a triazine with high electron-withdrawing properties.

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

R ₁ to R ₅ , Ar ₁ and Ar ₂ are the same or different from each other, and are each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to 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 It is selected from the group consisting of an alkyl boron group, a C ₆ to C ₆₀ aryl boron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ arylphosphine oxide group, and a C ₆ to C ₆₀ arylamine group. , or they can form a condensed ring with adjacent groups. At this time, as the adjacent group, R ₁ and another R ₁ or R ₃ and R ₄ may be combined with each other to form a condensed ring.

Preferably, R ₁ to R ₅ are the same 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, 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 arylamine group, or they are selected from the group adjacent to Condensed rings can be formed.

More preferably, R ₁ to R ₅ are the same or different from each other, and may each independently be selected from the group consisting of hydrogen, an aryl group of C ₆ to C ₆₀ , and a heteroaryl group of 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, * refers to the site bound to Formula 1.

More preferably, at least one of Ar ₁ and Ar ₂ may be a heteroaryl group. More specifically, 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.

The compound represented by Formula 1 of the present invention described above is the following exemplified 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 It may be further specified as a compound represented by any of K-129, L-1 to L-73. However, the compound represented by Formula 1 of the present invention is not limited to those exemplified below.

In the present invention, “alkyl” refers to a monovalent substituent derived from a straight-chain 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, and hexyl.

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

In the present invention, “alkynyl” refers to a monovalent substituent derived from a straight 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 ethynyl, 2-propynyl, etc., but are not limited thereto.

In the present invention, “cycloalkyl” refers to 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, and adamantine.

In the present invention, “heterocycloalkyl” refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or it is substituted with a hetero atom such as Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

In the present invention, “aryl” refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, either 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 also be included. Examples of such aryl include phenyl, naphthyl, phenanthryl, anthryl, etc., but are not limited thereto.

In the present invention, “heteroaryl” refers to 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, of the ring is replaced with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply pendant or condensed with each other may be included, and a condensed form with an aryl group may also be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, phenoxathienyl, indolizinyl, and indolyl ( Polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, etc., but are not limited thereto.

In the present invention, “alkyloxy” is a monovalent substituent represented by R'O-, where R' means alkyl having 1 to 40 carbon atoms. These alkyloxy may include linear, branched, or cyclic structures. Examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, etc., but are not limited thereto.

In the present invention, “aryloxy” is a monovalent substituent represented by RO-, where R refers to aryl having 6 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, etc., but are not limited thereto.

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, “alkylboron” refers to boron substituted with alkyl having 1 to 40 carbon atoms, and “arylboron” refers to boron substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "arylphosphine" refers to phosphine substituted with aryl having 6 to 60 carbon atoms, and "arylphosphine oxide group" refers to phosphine substituted with aryl having 6 to 60 carbon atoms containing 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” refers to an amine substituted with aryl having 6 to 60 carbon atoms.

The compound represented by Formula 1 of the present invention can be synthesized in various ways by referring to the synthesis process in the examples below.

2. Organic electroluminescent device

The present invention provides an organic electroluminescent device containing 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 a compound represented by Formula 1 above. At this time, the above compounds may be used alone, or two or more may be used in combination.

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 among these, at least one organic material layer may include a compound represented by Formula 1. there is. Specifically, it is preferable that the organic material layer containing the compound of Formula 1 is 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). Additionally, the light-emitting layer of the organic electroluminescent device of the present invention may include a compound other than the compound of Formula 1 above as a host.

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

Meanwhile, the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode using 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 material layer may be formed by vacuum deposition or solution application. 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, etc. can be used.

*284 In addition, the anode material includes 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 are not limited thereto.

Additionally, the cathode material may include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayer structure materials such as LiF/Al or LiO2/Al, etc., but are not limited thereto.

Additionally, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not particularly limited, and common materials known in the art can be used.

Hereinafter, the present invention will be described in detail through examples. However, the following examples are merely illustrative of 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), 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, it was extracted with methylene chloride, MgSO ₄ was added, and filtered. After removing the solvent in the filtered organic layer, the target compound, 2',6'-dibromo-5-chloro-2-methoxy-1,1'-biphenyl (316 g, yield 84%), was obtained using column chromatography.

¹ H-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, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 2',6'-dibromo-5-chloro-[1,1'-biphenyl]-2-ol (290 g, yield 95%) was obtained using column chromatography. got it

¹ H-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), 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, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 1-bromo-8-chlorodibenzo[b,d]furan (197 g, yield 88%), was obtained using column chromatography.

¹ H-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 it

¹ H-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 ) was added to 500 ml of DMF and stirred at 110°C for 5 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound Core-1 (120 g, yield 86%) was obtained using column chromatography.

¹ H-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 recrystallized to produce 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.

¹ H-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, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound Core-2 (50 g, yield 82%) was obtained using column chromatography.

¹ H-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, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 3-bromo-2,5'-dichloro-2'-methoxy-1,1'-biphenyl (2796 g, yield 84%), was obtained using column chromatography.

¹ H-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, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 3'-bromo-2',5-dichloro-[1,1'-biphenyl]-2-ol (280 g, yield 84%) was obtained using column chromatography. got it

¹ H-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), 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, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 6-bromo-2-chlorodibenzo[b,d]furan (200 g, yield 89%), was obtained using column chromatography.

¹ H-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 recrystallized to obtain the target compound, 3-(8-chlorodibenzo[b,d]furan-4-yl)-9-phenyl-9H-carbazole (118 g, yield 76%). got it

¹ H-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) was added to 200 ml of DMF and stirred at 110°C for 5 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound Core-3 (120 g, yield 85%) was obtained using column chromatography.

¹ H-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 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 produce 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.

¹ H-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, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound Core-4 (51 g, yield 84%) was obtained using column chromatography.

¹ H-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, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 4-bromo-2,5'-dichloro-2'-methoxy-1,1'-biphenyl (227 g, yield 68%), was obtained using column chromatography.

¹ H-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, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 4'-bromo-2',5-dichloro-[1,1'-biphenyl]-2-ol (185 g, yield 85%) was obtained using column chromatography. got it

¹ H-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), 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, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound, 7-bromo-2-chlorodibenzo[b,d]furan (164 g, yield 82%), was obtained using column chromatography.

¹ H-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 it

¹ H-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 ) was added to 500 ml of DMF and stirred at 110°C for 5 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound Core-5 (115 g, yield 80%) was obtained using column chromatography.

¹ H-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 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.

¹ H-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, 3 mmol), 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, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound Core-6 (45 g, yield 85%) was obtained using column chromatography.

¹ H-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 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.

¹ H-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, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound Core-7 (25 g, yield 71%) was obtained using column chromatography.

¹ H-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 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 produce 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.

¹ H-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, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound Core-8 (23 g, yield 85%) was obtained using column chromatography.

¹ H-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 it

¹ H-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 ) was added to 200 ml of DMF and stirred at 110°C for 5 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound Core-9 (138 g, yield 87%) was obtained using column chromatography.

¹ H-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 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 produce 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.

¹ H-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, 3 mmol), 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, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound Core-10 (39 g, yield 85%) was obtained using column chromatography.

¹ H-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 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]thiophen-2-yl)-9-phenyl-9H-carbazole (35 g, yield 76%). got it

¹ H-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) ) was added to 200 ml of DMF and stirred at 110°C for 5 hours. After completion of the reaction, the extract was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent in the filtered organic layer, the target compound Core-11 (30 g, yield 71%) was obtained using column chromatography.

¹ H-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 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 with 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 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 with 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 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 with 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 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 with 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 with 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 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 with silica, and then 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 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 with silica, and then 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 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 with silica, and then 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) 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 with 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 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 with silica, and 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 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 with silica, and 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 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 with 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 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 with 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 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 with silica, and then 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 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 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 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 with silica, and 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 with 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 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 with 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), 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 incubated at 110°C. It was stirred for 8 hours. After completion of the reaction, the produced solid was filtered. The filtered solid was dissolved in toluene, filtered with silica, and 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 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 with silica, and recrystallized to obtain the target compound, Compound L-51 (5.7 g, yield 76%).

[LCMS] : 746

[Example 1 and 20] Fabrication of a 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 subjected to high purity sublimation purification using a commonly known method. Then, a green organic electroluminescent device was manufactured according to the process below.

First, a glass substrate coated with a 1500 Å thin film of ITO (indium tin oxide) was washed with distilled water ultrasonic waves. After washing with distilled water, the substrate is ultrasonic cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech). Then, the substrate is cleaned using UV for 5 minutes and then vacuum evaporated. The substrate was transferred to .

On the ITO transparent electrode prepared in this way, m-MTDATA (60 nm)/TCTA (80 nm)/90% of the above synthesis example compound + 10% of Ir(ppy) ₃ (30 nm)/BCP (10 nm)/Alq ₃ ( An organic electroluminescent device was manufactured by stacking in the following order: 30 nm)/LiF (1 nm)/Al (200 nm).

[Comparative Example 1] Fabrication of green organic electroluminescent device

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

[Comparative Example 2] Fabrication of green organic electroluminescent device

A green organic electroluminescent device was manufactured in the same process as Example 1, except that Compound 1 was used instead of Compound A-1 as the 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 process as Example 1, except that Compound 2 was used instead of Compound A-1 as the 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 green organic electroluminescent device manufactured in Examples 1 to 20 and Comparative Examples 1 to 3, the driving voltage, current efficiency, and emission peak were measured at a current density of 10 mA/cm2, and the results are shown in Table 1 below. indicated.

Sample host driving voltage
(V) Luminescence 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 applying the compound according to the present invention to the light-emitting layer of the green organic electroluminescent device (Examples 1 to 20), the conventional CBP, Compounds 1 and 2 are applied to the light-emitting layer of the green organic electroluminescent device. It was found that better performance was achieved in terms of current efficiency and driving voltage compared to the case (Comparative Examples 1 to 3).

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 an arylene group of C ₆ to C ₁₈ and a heteroarylene group of 5 to 18 nuclear atoms,
Y is O or S,
Z ₁ to Z ₃ are N,
n is 0,
R ₁ , R ₃ and R ₄ are the same or different from each other, and are each independently hydrogen, deuterium, halogen group, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C It is selected from the group consisting of an alkynyl group of ₄₀ , an aryl group of C ₆ to C ₆₀ and a heteroaryl group of 5 to 60 nuclear atoms, or they may form a condensed ring with an adjacent group,
R3 and R4 are combined with each other to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, or a condensed heteroaromatic ring,
The compound represented by Formula 1 is represented by any one of the following Formulas 12 to 14,
[Formula 12]

[Formula 13]

[Formula 14]

Ar ₁ and Ar ₂ are the same or different from each other, and 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 is selected from the group consisting of aryl groups, or they can form a condensed ring with adjacent groups,
The arylene group and heteroarylene group of L, R ₁ , R ₃ to R ₅ , Ar ₁ and Ar ₂ alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyl oxide 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 with 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 arylphosphine group, C ₆ ~ C ₆₀ arylphosphine 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 or different from each other. According to paragraph 1,
The compound represented by Formula 1 is a compound represented by any one of the following Formulas 2 to 5.
[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. delete delete delete According to paragraph 1,
R ₁ , R ₃ and R ₄ 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 with 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 arylamine group, or they are condensed with adjacent groups A compound that can form a ring. According to paragraph 1,
A compound wherein Ar ₁ and Ar ₂ are substituents selected from the group consisting of the following structural formulas.

In the above structural formula,
* refers to the site bound to Formula 1. It includes an anode, a cathode, and one or more organic layers interposed between the anode and the cathode,
An organic electroluminescent device wherein at least one of the one or more organic layers includes the compound according to any one of claims 1, 2, 6, and 7. According to clause 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 clause 8,
An organic electroluminescent device in which the organic material layer containing the compound is a phosphorescent layer.