KR102592185B1 - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device containing the same. The compound according to the present invention is used in an organic material layer, preferably a light-emitting layer, of an organic electroluminescent device, such as luminous efficiency, driving voltage, and Lifespan can be improved.

Description

Organic compounds and organic electroluminescent devices containing the same {ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME}

The present invention relates to a new organic compound and an organic electroluminescent device containing the same, and more specifically, to a new organic compound having excellent hole injection ability, hole transport ability, luminescence ability, etc., and the luminous efficiency by including the compound as a material of the organic layer. , relates to an organic electroluminescent device with improved characteristics such as driving voltage and lifespan.

In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode, and electrons are injected into the organic material layer from the cathode. When the injected hole and electron meet, an exciton is formed, and when this exciton falls to the ground state, light is emitted. Materials included in the organic layer may be classified into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc., depending on their functions.

The light-emitting material can be divided into blue, green, and red light-emitting materials depending on the color of the light, and yellow and orange light-emitting materials necessary to achieve better natural colors. Additionally, a host/dopant system can be used as a light-emitting material to increase color purity and increase luminous efficiency through energy transfer.

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. At this time, since phosphorescent dopants can theoretically improve luminous efficiency by up to 4 times compared to fluorescent dopants, much research is being conducted on phosphorescent hosts as well as phosphorescent dopants.

Anthracene derivatives are currently known as fluorescent dopant/host materials used in the light-emitting layer. In addition, metal complex compounds containing Ir such as Firpic, Ir(ppy) ₃ and (acac)Ir(btp) ₂ are known as phosphorescent dopant materials used in the light-emitting layer, and 4,4-dicarbazolybiphenyl as a phosphorescent host material. (CBP) is known.

However, existing materials have a low glass transition temperature and poor thermal stability, so they are not satisfactory in terms of lifespan in organic electroluminescent devices, and improvement in light emitting properties is still needed.

Republic of Korea Patent Publication No. 2013-0049275

The purpose of the present invention is to provide an organic compound that has excellent luminescence ability, hole transport ability, hole injection ability, etc. and can be used as a material for an organic layer.

Another object of the present invention is to provide an organic electroluminescent device containing the organic compound, which has a low driving voltage, high luminous efficiency, and improved lifespan.

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

In Formula 1,

A is a 5-membered ring containing or not containing one atom of S, O and N,

Ar ₁ is selected from the group consisting of hydrogen, an aryl group having C ₆ to C ₆₀ and a heteroaryl group having 5 to 60 nuclear atoms,

L ₁ and L ₂ are the same or different from each other and are each independently selected from the group consisting of a single bond, an arylene group of C ₆ to C ₁₈ and a heteroarylene group of 5 to 18 nuclear atoms, where L ₁ is _{1 , _ _}

X ₁ is NR ₁ or CR ₂ R ₃ ,

_{X 2 to _ _ _ _} , except for the case where both X ₃ and X ₄ are single bonds,

Y ₁ to Y ₈ and Y ₁₁ to Y ₁₈ are each independently CR ₇ , wherein a plurality of R ₇ is the same or different from each other,

R ₁ to R ₇ are the same or different from each other, and are each independently 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, or bonded to an adjacent group to form a condensed aromatic ring or Forms a condensed heteroaromatic ring,

The 5-membered ring of A, the aryl group and heteroaryl group of Ar ₁ , the arylene group and heteroarylene group of L ₁ and L ₂ , and the aryl group and heteroaryl group of R ₁ to R ₇ are each independently Deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, 5 to 5 nuclear atoms. 60 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 ₂ ~ 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 arylamine group. It is substituted or unsubstituted with one or more selected substituents, and when the substituents are plural, they may be the same or different from each other.

In addition, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers contains a compound represented by the formula (1). It provides an organic electroluminescent device comprising:

Meanwhile, 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 thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc., but are not limited thereto.

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 thereof 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 thereof include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Polycyclics such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl ring; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, 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 thereof include phenyloxy, naphthyloxy, diphenyloxy, etc., but are not limited thereto.

In the present invention, alkyloxy is a monovalent substituent represented by R'O-, where R' refers to alkyl having 1 to 40 carbon atoms, and includes a linear, branched, or cyclic structure. can do. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

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

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 thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, etc., but are not limited thereto.

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 Se. It is substituted with a hetero atom such as Examples thereof include morpholine, piperazine, 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.

Since the compound according to the present invention is excellent in heat resistance, hole injection ability, hole transport ability, luminescence ability, etc., it can be used as an organic material layer material, preferably a light emitting layer material, of an organic electroluminescent device.

In addition, the organic electroluminescent device containing the compound according to the present invention in the organic material layer can greatly improve aspects such as light emission performance, driving voltage, lifespan, and efficiency, and such organic electroluminescent device can be effectively applied to full color display panels, etc. there is.

Hereinafter, the present invention will be described.

1. Novel organic compounds

The organic compound of the present invention is a 'moiety in which a pyrimidine and a five-membered ring (A) are condensed', and a carbazole moiety, a dimethylfluorene moiety, a dibenzothiophene moiety, and dibenzofuran. The basic skeleton is a structure that combines (dibenzofuran) moiety, dimethylacridine moiety, thianthrene moiety, dibenzodioxin moiety, and spirofluorene, etc. It is a compound represented by Formula 1 above.

More specifically, the compound represented by Formula 1 of the present invention has a 5-membered ring (A) such as cyclopentane, furan, pyrazole, imidazole, oxazole, thiophene, etc. bonded to a pyrimidine, and has an energy similar to that of quinazoline. Because it has a high level, it can be adjusted to be higher than the energy level of the dopant, so it can be used as a host material, and because it has a higher triplet energy than the quinazoline-bound structure, it is expected to increase excellent efficiency when used as a light-emitting layer material for organic electroluminescent devices. You can. In particular, compounds in which a thiophene is bonded to a pyrimidine can exhibit a longer wavelength than compounds in which another five-membered ring is bonded to a pyrimidine. Additionally, when an aryl group (eg, phenyl, biphenyl) is introduced into the five-membered ring (A), thermal stability is improved by blocking the reaction site.

The compound represented by Formula 1 of the present invention has a high molecular weight and glass transition temperature, and thus has excellent thermal stability. In addition, because it has a narrow band gap and HOMO and LUMO energy levels suitable for the host material of the organic layer, it has excellent carrier transport and luminescence properties. In addition, the compound represented by Formula 1 of the present invention is used as a material for the organic layer because an electron donating group (EDG) with large electron donation, such as an arylamine group, carbazole group, terphenyl group, triphenylene group, etc., is bonded to the basic skeleton. When used, injection and transport of holes can be smoothly achieved.

Therefore, the compound represented by Formula 1 of the present invention is an organic layer material of an organic electroluminescent device, preferably a light-emitting layer material (red phosphorescent host material), an electron transport/injection layer material, a hole transport/injection layer material, and a light-emitting auxiliary layer. It can be usefully used as a material, a lifespan improvement layer material, more preferably a light-emitting layer material, an electron injection layer material, a light-emitting auxiliary layer material, and a lifespan improvement layer material.

Meanwhile, in the phosphorescent layer of an organic electroluminescent device, the triplet energy gap of the host material must be higher than the triplet energy gap of the dopant material. That is, when the lowest excited state of the host has higher energy than the lowest emission state of the dopant, phosphorescence emission efficiency can be improved. The compound represented by Formula 1 of the present invention is a basic skeleton in which moieties such as indazole, imidazole, oxazole, and thiophene, which have a high triplet energy and a wide singlet energy level and a high triplet energy level, are combined. Because a specific substituent is introduced in , the energy level is higher than that of the dopant, so it can be used as a host material.

Additionally, because the compound of the present invention has high triplet energy, it can prevent excitons generated in the light-emitting layer from diffusing into the electron transport layer or hole transport layer adjacent to the light-emitting layer. Therefore, when forming an organic material layer (light-emitting auxiliary layer) existing between the hole transport layer and the light-emitting layer using the compound represented by Formula 1 of the present invention, diffusion of excitons is prevented, thereby substantially contributing to light emission within the light-emitting layer. By increasing the number of excitons, the luminous efficiency of the organic electroluminescent device can be improved.

In addition, even when forming an organic material layer (life improvement layer) between the light emitting layer and the electron transport layer using the compound represented by Formula 1 of the present invention, diffusion of excitons is prevented, thereby improving the durability, stability, and stability of the organic electroluminescent device. Lifespan can be improved.

The compound represented by Formula 1 of the present invention may be embodied as a compound represented by Formulas 2 to 5 below.

In Formulas 2 to 5,

_{Descriptions of A , Ar 1 , X 1 to}

Specifically, the compound represented by Formula 1 of the present invention may be selected from the group consisting of compounds represented by Formulas 6 to 8 below.

In Formulas 6 to 8,

_{Descriptions of A} , _{Ar 1 , X 3 ,}

Additionally, the compound represented by Formula 1 of the present invention may be selected from the group consisting of compounds represented by Formulas 9 to 11 below.

In Formulas 9 to 11,

_{The description of A , Ar 1 ,} X _{1 ,}

로 표시되는 모이어티는 하기 S-1 내지 S-8로 표시되는 모이어티로 이루어진 군에서 선택되는 것이 바람직하다.In the compound represented by Formula 1 of the present invention,

The moiety represented by is preferably selected from the group consisting of moieties represented by S-1 to S-8 below.

The compound represented by Formula 1 of the present invention may be specified as the following compounds R1 to R620, but is not limited to these.

2. Organic electric field light emitting element

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

Specifically, the organic electroluminescent device of 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 is Includes a compound represented by Formula 1. At this time, the above compounds may be included alone, or two or more may be included in a mixed state.

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, a lifespan improvement layer, an electron transport layer, and an electron injection layer, of which at least one organic material layer is a compound represented by Formula 1. may include. Specifically, it is preferable that the organic material layer containing the compound represented by Formula 1 is a light-emitting layer.

Specifically, the light-emitting layer may include a host, and in this case, the host may include the compound represented by Formula 1 alone or may include the compound represented by Formula 1 together with another compound as the host.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but 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, a lifespan improvement layer, an electron transport layer, and a cathode are sequentially stacked. At this time, an electron injection layer may be additionally laminated on the electron transport layer. Additionally, an insulating layer or adhesive layer may be further laminated at the interface between the electrode (cathode or anode) and the organic material layer.

The organic electroluminescent device of the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic layers includes the compound represented by Formula 1 above.

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, etc. can be used.

Additionally, the anode material is not particularly limited, but may include 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 can be used.

Additionally, the cathode material is not particularly limited, but may include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multi-layer structure materials such as LiF/Al or LiO2/Al can be used.

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 A1

Under a nitrogen stream, 5.0g (16.9 mmol) of 10-bromo-7H-benzo[c]carbazole, 5.8g (20.2 mmol) of 9-phenyl-9H-carbazol-3-ylboronic acid, 1.0g (5) of Pd(PPh ₃ ) ₄ mol%), and 7.0 g (50.6 mmol) of potassium carbonate were added to 80 ml/40 ml/40 ml of Toluene/H ₂ O/Ethanol and stirred at 110°C for 3 hours. After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A1 (5.6 g, 12.1 mmol, yield 72%).

GC-Mass (theoretical value: 458.55 g/mol, measured value: 458 g/mol)

¹ H-NMR: δ 7.25~7.28(m, 2H), 7.50~7.67(m, 13H), 7.85~7.91(m, 3H), 8.15(d, 1H), 8.48(t, 2H), 10.01(s) , 1H)

[ Preparation example 2] Synthesis of A2

2-(10-bromo-7H-benzo[c]carbazol-7-yl)-4,6-diphenylthieno[3,2-d]pyrimidine 9.8g (16.9 mmol), 9H-carbazol-3-ylboronic under nitrogen flow. Add 4.3g (20.2 mmol) of acid, 1.0g (5 mol%) of Pd(PPh ₃ ) ₄ and 7.0g (50.6 mmol) of potassium carbonate to 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol and stir at 110°C. Stirred for an hour. After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, the product was purified by column chromatography to obtain the target compound, A2 (7.9 g, 11.8 mmol, yield 70%).

GC-Mass (theoretical value: 668.81g/mol, measured value: 668g/mol)

¹ H-NMR: δ 7.25~7.28(m, 2H), 7.41~7.48(m, 7H), 7.58~7.75(m, 13H), 8.05(d, 1H), 8.13~8.14(m, 3H), 8.48 (d, 1H), 10.01(s, 1H)

[ Preparation example 3] Synthesis of A3

10-bromo-7H-benzo[c]carbazole 5.0 (16.8 mmol), 9-(4,6-diphenylthieno[3,2-d]pyrimidin-2-yl)-9H-carbazol-3-ylboronic acid under nitrogen flow. Add 10.2g (20.2 mmol), 0.6g (5 mol%) of Pd(PPh ₃ ) ₄ and 7.0g (50.6 mmol) of potassium carbonate to 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol and simmer at 110°C for 3 hours. It was stirred for a while. After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A3 (7.9 g, 11.8 mmol, yield 70%).

GC-Mass (theoretical value: 668.81g/mol, measured value: 668g/mol)

¹ H-NMR: δ 7.25~7.49(m, 9H), 7.63~7.78(m, 15H), 8.15(d, 1H), 8.54~855(t, 2H), 10.01(s, 1H)

[ Preparation example 4] Synthesis of A4

Under nitrogen stream, 5.0g (16.9 mmol) of 10-bromo-7H-benzo[c]carbazole, 6.8g (20.2 mmol) of 7-phenyl-7H-benzo[c]carbazol-10-ylboronic acid, Pd(PPh ₃ ) ₄ 1.0g (5 mol%) and 7.0g (50.6 mmol) of potassium carbonate were added to 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol and stirred at 110°C for 3 hours. After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A4 (6.4 g, 12.7 mmol, yield 75%).

GC-Mass (theoretical value: 508.61g/mol, measured value: 508g/mol)

¹ H-NMR: δ 7.45~7.63(m, 15H), 7.88~7.93(m, 4H), 8.15(d, 2H), 8.50(d, 2H), 10.01(s, 1H)

[ Preparation example 5] Synthesis of A5

10-bromo-7H-benzo[c]carbazole 5.0g (16.9 mmol), 7-(4,6-diphenylthieno[3,2-d]pyrimidin-2-yl)-7H-benzo[c]carbazol under nitrogen flow. Add 11.1g (20.2 mmol) of -10-ylboronic acid, 1.0g (5 mol%) of Pd(PPh ₃ ) ₄ and 7.0g (50.6 mmol) of potassium carbonate and 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol. It was stirred at 110°C for 3 hours. After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A5 (9,1g, 12.7mmol, yield 75%).

GC-Mass (theoretical value: 718.87g/mol, measured value: 718g/mol)

¹ H-NMR: δ 7.23(s, 1H), 7.41~7.48(m, 6H), 7.62~7.88(m, 18H), 8.15(d, 2H), 8.53(d, 2H), 10.01(s, 1H) )

[ Preparation example 6] Synthesis of A6

10-bromo-7H-benzo[c]carbazole 5.0g (16.9 mmol), 9-(4,6-diphenylthieno[3,2-d]pyrimidin-2-yl)-6-phenyl-9H-carbazol under nitrogen flow. Add 11.1g (20.2 mmol) of -3-ylboronic acid, 1.0g (5 mol%) of Pd(PPh ₃ ) ₄ and 7.0g (50.6 mmol) of potassium carbonate to 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol. It was stirred at 110°C for 3 hours. After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A6 (9,0g, 12.1mmol, yield 72%).

GC-Mass (theoretical value: 744.90 g/mol, measured value: 744 g/mol)

¹ H-NMR: δ 7.23(s, 1H), 7.41~7.53(m, 11H), 7.62~7.79(m, 15H), 8.01(d, 1H), 8.16~8.17(m, 2H), 8.53(d) , 1H), 10.01(s, 1H)

[ Preparation example 7] Synthesis of A7

Under nitrogen stream, 5.0g (16.9 mmol) of 10-bromo-7H-benzo[c]carbazole, 7.4g (20.2 mmol) of 3-(9-phenyl-9H-carbazol-3-yl)phenylboronic acid, Pd(PPh ₃ ) ₄ 1.0g (5 mol%) and 7.0g (50.6 mmol) of potassium carbonate were added to 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol and stirred at 110°C for 3 hours. After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A7 (6.5 g, 12.1 mmol, yield 72%).

GC-Mass (theoretical value: 534.65 g/mol, measured value: 534 g/mol)

¹ H-NMR: δ 7.25(m, 1H), 7.51~7.69(m, 18H), 7.82(d, 1H), 8.01(d, 1H), 8.14~8.17(m, 3H), 8.53(d, 1H) ), 10.01(s, 1H)

[ Preparation example 8] Synthesis of A8

Under nitrogen flow, 10-bromo-7H-benzo[c]carbazole 9.8g (16.9 mmol), 9-phenyl-9'-(4-phenylquinazolin-2-yl)-9H,9'H-3,3'-bicarbazol Add 13.3g (20.2 mmol) of -6-ylboronic acid, 1.0g (5 mol%) of Pd(PPh ₃ ) ₄ and 7.0g (50.6 mmol) of potassium carbonate to 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol. It was stirred at 110°C for 3 hours. After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A8 (9.8 g, 11.8 mmol, yield 70%).

GC-Mass (theoretical value: 827.97g/mol, measured value: 827g/mol)

¹ H-NMR: δ 7.25(m, 1H), 7.43~7.78(m, 25H), 8.02~8.17(m, 9H), 8.53(d, 1H), 10.01(s, 1H)

[ Preparation example 9] Synthesis of A9

Under a nitrogen stream, 5.0g (16.9 mmol) of 2-bromo-5H-benzo[b]carbazole, 5.8g (20.2 mmol) of 9-phenyl-9H-carbazol-3-ylboronic acid, 1.0g (5) of Pd(PPh ₃ ) ₄ mol%) and 7.0 g (50.6 mmol) of potassium carbonate were added to 80 ml/40 ml/40 ml of Toluene/H ₂ O/Ethanol and stirred at 110°C for 3 hours. After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A9 (5.4g, 11.8mmol, yield 70%).\

GC-Mass (theoretical value: 458.55 g/mol, measured value: 458 g/mol)

¹ H-NMR: δ 7.28~7.59(m, 16H), 7.88~7.93(m, 3H), 8.15(d, 1H), 8.54(d, 1H), 10.01(s, 1H)

[ Preparation example 10] Synthesis of A10

Under a nitrogen stream, 5.0g (16.9 mmol) of 8-bromo-11H-benzo[a]carbazole, 5.8g (20.2 mmol) of 9-phenyl-9H-carbazol-3-ylboronic acid, 1.0g (5) of Pd(PPh ₃ ) ₄ mol%) and 7.0 g (50.6 mmol) of potassium carbonate were added to 80 ml/40 ml/40 ml of Toluene/H ₂ O/Ethanol and stirred at 110°C for 3 hours. After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A10 (5.4 g, 11.8 mmol, yield 70%).

GC-Mass (theoretical value: 458.55 g/mol, measured value: 458 g/mol)

¹ H-NMR: δ 7.27~7.33(m, 2H), 7.42~7.65(m, 12H), 7.77~7.84(m, 3H), 8.12~8.14(m, 2H), 8.52~8.54(m, 2H) , 10.01(s, 1H)

[ Preparation example 11] Synthesis of A11

Under nitrogen flow, 10-bromo-7-(4-phenylquinazolin-2-yl)-7H-benzo[c]carbazole 8.4g (16.9 mmol), 9-phenyl-9H-carbazole-3,6-diyldiboronic acid 6.7g ( 20.2 mmol), 1.0 g (5 mol%) of Pd(PPh ₃ ) ₄ and 7.0 g (50.6 mmol) of potassium carbonate were added to 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol and stirred at 110°C for 3 hours. . After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A11 (8.9 g, 12.7 mmol, yield 75%).

GC-Mass (theoretical value: 706.60g/mol, measured value: 706g/mol)

¹ H-NMR: δ 2.0 (s, 2H), 7.45 - 7.58 (m, 15H), 7.72 - 7.78 (m, 5H), 8.02 - 8.06 (m, 4H), 8.16 - 8.18 (m, 4H), 8.54 (d, 1H)

[ Preparation example 12] Synthesis of A12

Under a nitrogen stream, 5.0 g (16.9 mmol) of 10-bromo-7H-benzo[c]carbazole, 4.8 g (20.2 mmol) of 9,9-dimethyl-9H-fluoren-2-ylboronic acid, 1.0 g of Pd(PPh ₃ ) ₄ (5 mol%) and 7.0 g (50.6 mmol) of potassium carbonate were added to 80 ml/40 ml/40 ml of Toluene/H ₂ O/Ethanol and stirred at 110°C for 3 hours. After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A12 (5.0 g, 12.1 mmol, yield 72%).

GC-Mass (theoretical value: 409.52g/mol, measured value: 409g/mol)

¹ H-NMR: δ 1.73(m, 6H), 7.25(m, 1H), 7.34(m, 1H), 7.55~7.62(m, 7H), 7.76(s, 2H), 7.76~7.79(m, 3H) ), 8.16(d, 1H), 8.54(d, 1H), 10.01(s, 1H)

[ Preparation example 13] Synthesis of A13

Under a nitrogen stream, 10-bromo-7H-benzo[c]carbazole 5.0g (16.9 mmol), dibenzo[b,d]thiophen-2-ylboronic acid 4.6 g (20.2 mmol), Pd(PPh ₃ ) ₄ 1.0g (5) mol%) and 7.0 g (50.6 mmol) of potassium carbonate were added to 80 ml/40 ml/40 ml of Toluene/H ₂ O/Ethanol and stirred at 110°C for 3 hours. After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A13 (4.7 g, 11.8 mmol, yield 70%).

GC-Mass (theoretical value: 399.51 g/mol, measured value: 399 g/mol)

¹ H-NMR: δ 7.50~7.51(m, 2H), 7.65~7.76(m, 6H), 7.88~7.89(m, 2H), 7.98~8.00(m, 3H), 8.15(d, 1H), 8.45 ~8.49(d, 2H), 10.01(s, 1H)

[ Preparation example 14] Synthesis of A14

Under a nitrogen stream, 10-bromo-7H-benzo[c]carbazole 5.0g (16.9 mmol), dibenzo[b,d]furan-2-ylboronic acid 4.3 g (20.2 mmol), Pd(PPh ₃ ) ₄ 1.0g (5 mol%) and 7.0 g (50.6 mmol) of potassium carbonate were added to 80 ml/40 ml/40 ml of Toluene/H ₂ O/Ethanol and stirred at 110°C for 3 hours. After completion of the reaction, the organic layer was separated using methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A14 (4.5 g, 11.8 mmol, yield 70%).

GC-Mass (theoretical value: 383.44 g/mol, measured value: 383 g/mol)

¹ H-NMR: δ 7.35~7.38(m, 2H), 7.65~7.85 (m, 12H), 8.15(d, 1H), 8.53(d, 1H), 10.01(s, 1H)

[ Preparation example 15] Synthesis of A15

Under a nitrogen stream, 5.0 g (16.9 mmol) of 10-bromo-7H-benzo[c]carbazole, 7.3 g (20.2 mmol) of 9,9'-spirobi[fluorene]-2-ylboronic acid, 1.0 g of Pd(PPh ₃ ) ₄ (5 mol%) and 7.0 g (50.6 mmol) of potassium carbonate were added to 80 ml/40 ml/40 ml of Toluene/H ₂ O/Ethanol and stirred at 110°C for 3 hours. After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A15 (9.0 g, 12.1 mmol, yield 72%).

GC-Mass (theoretical value: 531.64 g/mol, measured value: 531 g/mol)

¹ H-NMR: δ 7.16~7.35(m, 8H), 7.65~7.75(m, 11H), 7.86~7.89(m, 3H), 8.16(d, 1H), 8.54(d, 1H), 10.01(s) , 1H)

[ Preparation example 16] Synthesis of A16

Under a nitrogen stream, 5.0 g (16.9 mmol) of 10-bromo-7H-benzo[c]carbazole, 5.3 g (20.2 mmol) of thianthren-2-ylboronic acid, 1.0 g (5 mol%) of Pd(PPh ₃ ) ₄ and potassium carbonate 7.0g (50.6 mmol) was added to 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol and stirred at 110°C for 3 hours. After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A16 (5.2 g, 12.0 mmol, yield 71%).

GC-Mass (theoretical value: 431.57g/mol, measured value: 431g/mol)

¹ H-NMR: δ 6.99(m, 2H), 7.21~7.24(m, 5H), 7.63~7.67(m, 5H), 7.76(s, 1H), 7.87(d, 1H), 8.15(d, 1H) ), 8.54(d, 1H), 10.01(s, 1H)

[ Preparation example 17] Synthesis of A17

Under a nitrogen stream, 5.0 g (16.9 mmol) of 10-bromo-7H-benzo[c]carbazole, 4.6 g (20.2 mmol) of dibenzo[b,e][1,4]dioxin-2-ylboronic acid, and Pd(PPh ₃ ) ₄ 1.0g (5 mol%) and 7.0g (50.6 mmol) of potassium carbonate were added to 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol and stirred at 110°C for 3 hours. After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A17 (4.9 g, 12.1 mmol, yield 72%).

GC-Mass (theoretical value: 399.44 g/mol, measured value: 399 g/mol)

¹ H-NMR: δ 6.83(m, 2H), 7.13~7.16(m, 3H), 7.41~7.43(m, 2H), 7.63~7.67(m, 5H), 7.76(s, 1H), 7.87(d) , 1H), 8.15(d, 1H), 8.54(d, 1H), 10.01(s, 1H)

[ Preparation example 18] Synthesis of A18

Under a nitrogen stream, 5.0 g (16.9 mmol) of 10-bromo-7H-benzo[c]carbazole, 9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-ylboronic acid 6.7 g (20.2 mmol), Pd ( 1.0 g (5 mol%) of PPh ₃ ) ₄ and 7.0 g (50.6 mmol) of potassium carbonate were added to 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol and stirred at 110°C for 3 hours. After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A18 (6.1 g, 12.1 mmol, yield 72%).

GC-Mass (theoretical value: 500.63g/mol, measured value: 500g/mol)

¹ H-NMR: δ 1.72 (m, 6H), 6.35 - 6.54 (m, 3H), 6.73 - 6.79 (m, 4H), 7.11 - 7.20 (m, 5H), 7.63 - 7.68 (m, 5H), 7.76 (s, 1H), 7.87(d, 1H), 8.15(d, 1H), 8.54(d, 1H), 10.01(s, 1H)

[ Preparation example 19] Synthesis of A19

Under nitrogen flow, 10-bromo-7-(4-phenylbenzo[h]quinazoline-2-yl)-7H-benzo[c]carbazole 9.3g (16.9 mmol), 9-phenyl-9H-carbazole-3,6-diyldiboronic Add 6.7g (20.2 mmol) of acid, 1.0g (5 mol%) of Pd(PPh ₃ ) ₄ , 7.0g (50.6 mmol) of potassium carbonate, and 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol and mix 3 at 110°C. Stirred for an hour.

After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A19 (9,2g, 12.1mmol, yield 72%).

GC-Mass (theoretical value: 756.66g/mol, measured value: 756g/mol)

1H-NMR: δ 2.0(s, 2H), 7.45~8.12(m, 27H), 8.16~8.81(m, 3H), 8.54(d, 1H)

[ Preparation example 20] Synthesis of A20

Under nitrogen flow, 10-bromo-7-(4-phenylquinazoline-2-yl)-7H-benzo[c]carbazole 8.4g (16.9 mmol), 9,9-dimethyl-9H-fluorene-2,7-diyldiboronic acid 5.7 g (20.2 mmol), 1.0 g (5 mol%) of Pd(PPh ₃ ) ₄ , and 7.0 g (50.6 mmol) of potassium carbonate and 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol were added and incubated at 110°C for 3 hours. It was stirred.

After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A20 (7.8 g, 11.8 mmol, yield 70%).

GC-Mass (theoretical value: 657.57g/mol, measured value: 657g/mol)

1H-NMR: δ 1.72(s, 6H), 2.0(s, 2H), 7.17(d, 1H), 7.34(s, 1H), 7.41(m, 1H), 7.51(m, 2H), 7.56(s , 1H), 7.64~7.67(m, 5H), 7.78~8.03(m, 9H), 8.16~8.81(m, 3H), 8.54(d, 1H)

[ Synthesis example 1] Synthesis of R41

Under nitrogen stream, A1 5.6g (12.1mmol), 2-chloro-4,6-diphenylthieno[3,2-d]pyrimidine 4.3g (13.4mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), tri - 0.1g (0.6mmol) of tert -butylphosphine and 3.5g (36.4mmol) of sodium tert-butoxide were added to 100ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 5.9g (7.9mmol, yield 65%) of R41, the target compound, was obtained.

GC-Mass (theoretical value: 744.90 g/mol, measured value: 744 g/mol)

[ Synthesis example 2] Synthesis of R42

Under nitrogen stream, A1 5.6g (12.1mmol), 2-chloro-4,6-diphenylthieno[2,3-d]pyrimidine 4.3g (13.4mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), tri - 0.1g (0.6mmol) of tert -butylphosphine and 3.5g (36.4mmol) of sodium tert-butoxide were added to 100ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 5.9g (7.9mmol, yield 65%) of R42, the target compound, was obtained.

GC-Mass (theoretical value: 744.90 g/mol, measured value: 744 g/mol)

[ Synthesis example 3] Synthesis of R43

Under nitrogen stream, A1 5.6g (12.1mmol), 2-chloro-6-phenyl-4-(9-phenyl-9H-carbazol-3-yl)thieno[3,2-d]pyrimidine 6.5g (13.4mmol), 0.6 g (5 mol%) of Pd ₂ (dba) _3, 0.1 g (0.6 mmol) of tri- tert -butylphosphine, and 3.5 g (36.4 mmol) of sodium tert-butoxide were added to 100 ml of toluene and stirred at 110°C for 4 hours. . After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 7.0g (7.7mmol, yield 63%) of R43, the target compound, was obtained.

GC-Mass (theoretical value: 910.09 g/mol, measured value: 910 g/mol)

[ Synthesis example 4] Synthesis of R44

Under a nitrogen stream, A1 5.6g (12.1mmol), 4-(2-chloro-6-phenylthieno[3,2-d]pyrimidin-4-yl)-N,N-diphenylaniline 6.5g (13.4mmol), Pd ₂ ( dba) ₃ 0.6g (5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and sodium tert-butoxide 3.5g (36.4mmol) were added to 100ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 6.8g (7.4mmol, yield 61%) of R44, the target compound, was obtained.

GC-Mass (theoretical value: 912.11g/mol, measured value: 912g/mol)

[ Synthesis example 5] Synthesis of R45

Under nitrogen air flow, A3 7.9g (11.8mmol), bromobenzene 2.0g (13.0mmol), Pd ₂ (dba) ₃ 0.7g (5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 4.1 g (35.4 mmol) was added to 100 ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 5.7g (7.7mmol, yield 65%) of R45, the target compound, was obtained.

GC-Mass (theoretical value: 744.90 g/mol, measured value: 744 g/mol)

[ Synthesis example 6] Synthesis of R484

Under nitrogen flow, A2 7.9g (11.8mmol), 2-chloro-4-phenylquinazoline 6.6g (13.0mmol), Pd ₂ (dba) ₃ 0.7g (5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and 4.1 g (35.4 mmol) of sodium tert-butoxide were added to 100 ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 6.7g (7.7mmol, yield 65%) of R484, the target compound, was obtained.

GC-Mass (theoretical value: 873.03g/mol, measured value: 873g/mol)

[ Synthesis example 7] Synthesis of R281

Under nitrogen stream, A4 6.4g (12.7mmol), 2-chloro-4,6-diphenylthieno[3,2-d]pyrimidine 4.5g (13.9mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), tri - 0.1g (0.6mmol) of tert -butylphosphine and 3.6g (38.0mmol) of sodium tert-butoxide were added to 100ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 6.6g (8.4mmol, yield 66%) of R281, the target compound, was obtained.

GC-Mass (theoretical value: 794.96 g/mol, measured value: 794 g/mol)

[ Synthesis example 8] Synthesis of R283

Under nitrogen stream, A4 6.4g (12.7mmol), 2-chloro-6-phenyl-4-(9-phenyl-9H-carbazol-3-yl)thieno[3,2-d]pyrimidine 6.8g (13.9mmol), 0.6 g (5 mol%) of Pd ₂ (dba) _3, 0.1 g (0.6 mmol) of tri- tert -butylphosphine, and 3.6 g (38.0 mmol) of sodium tert-butoxide were added to 100 ml of toluene and stirred at 110°C for 4 hours. . After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 8.0g (8.4mmol, yield 66%) of R283, the target compound, was obtained.

GC-Mass (theoretical value: 960.15 g/mol, measured value: 960 g/mol)

[ Synthesis example 9] Synthesis of R284

Under a nitrogen stream, A4 6.4g (12.7mmol), 4-(2-chloro-6-phenylthieno[3,2-d]pyrimidin-4-yl)-N,N-diphenylaniline 6.8g (13.9mmol), Pd ₂ ( dba) ₃ 0.6g (5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and sodium tert-butoxide 3.6g (38.0mmol) were added to 100ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 8.0g (8.4mmol, yield 66%) of R284, the target compound, was obtained.

GC-Mass (theoretical value: 962.17g/mol, measured value: 962g/mol

[ Synthesis example 10] Synthesis of R300

Under nitrogen stream, A5 9.1g (12.7mmol), 2-chloro-4-phenylquinazoline 3.3g (13.9mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and 3.6 g (38.0 mmol) of sodium tert-butoxide were added to 100 ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 7.6g (8.2mmol, yield 65%) of R300, the target compound, was obtained.

GC-Mass (theoretical value: 923.09 g/mol, measured value: 923 g/mol)

[ Synthesis example 11] Synthesis of R299

Under nitrogen stream, A5 9.1g (12.7mmol), 2-bromodibenzo[b,d]furan 3.4g (13.9mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), tri- tert -butylphosphine 0.1g (0.6) mmol) and 3.6 g (38.0 mmol) of sodium tert-butoxide were added to 100 ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 6.9g (7.8mmol, yield 62%) of R299, the target compound, was obtained.

GC-Mass (theoretical value: 885.04g/mol, measured value: 885g/mol)

[ Synthesis example 12] Synthesis of R496

Under nitrogen flow, A6 9.1g (12.1mmol), bromobenzene 3.4g (13.9mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), tri- tert -butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.6. g (38.0 mmol) was added to 100 ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 6.9g (7.8mmol, yield 62%) of R496, the target compound, was obtained.

GC-Mass (theoretical value: 821.00g/mol, measured value: 821g/mol)

[ Synthesis example 13] Synthesis of R485

Under nitrogen stream, A7 6.5g (12.1mmol), 2-chloro-4,6-diphenylthieno[2,3-d]pyrimidine 4.3g (13.4mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), tri - 0.1g (0.6mmol) of tert -butylphosphine and 3.5g (36.4mmol) of sodium tert-butoxide were added to 100ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 6.4g (7.8mmol, yield 64%) of R485, the target compound, was obtained.

GC-Mass (theoretical value: 821.00g/mol, measured value: 821g/mol)

[ Synthesis example 14] Synthesis of R491

Under nitrogen stream, A8 9.8g (11.8mmol), 2-chloro-4,6-diphenylthieno[3,2-d]pyrimidine 4.2g (13.0mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), tri - 0.1g (0.6mmol) of tert -butylphosphine and 3.4g (35.4mmol) of sodium tert-butoxide were added to 100ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 8.0g (7.2mmol, yield 61%) of R491, the target compound, was obtained.

GC-Mass (theoretical value: 1114.32g/mol, measured value: 1114g/mol)

[ Synthesis example 15] Synthesis of R121

Under nitrogen stream, A9 5.4g (11.8mmol), 2-chloro-4,6-diphenylthieno[2,3-d]pyrimidine 4.2g (13.0mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), tri - 0.1g (0.6mmol) of tert -butylphosphine and 3.4g (35.4mmol) of sodium tert-butoxide were added to 100ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 5.4 g (7.2 mmol, yield 61%) of R121, the target compound, was obtained.

GC-Mass (theoretical value: 744.90 g/mol, measured value: 744 g/mol)

[ Synthesis example 16] Synthesis of R181

Under nitrogen stream, A10 5.4g (11.8mmol), 2-chloro-4,6-diphenylthieno[2,3-d]pyrimidine 4.2g (13.0mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), tri - 0.1g (0.6mmol) of tert -butylphosphine and 3.4g (35.4mmol) of sodium tert-butoxide were added to 100ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 5.4 g (7.2 mmol, yield 61%) of R181, the target compound, was obtained.

GC-Mass (theoretical value: 744.90 g/mol, measured value: 744 g/mol)

[ Synthesis example 17] Synthesis of R498

Under nitrogen stream, A11 8.9g (12.7mmol), 2-chloro-4,6-diphenylthieno[2,3-d]pyrimidine 4.5g (13.9mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), tri - 0.1g (0.6mmol) of tert -butylphosphine and 3.6g (38.0mmol) of sodium tert-butoxide were added to 100ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 7.3g (7.7mmol, yield 61%) of R498, the target compound, was obtained.

GC-Mass (theoretical value: 949.13 g/mol, measured value: 949 g/mol)

[ Synthesis example 18] Synthesis of R501

Under a nitrogen stream, A1 5.6g (12.1mmol), 2-chloro-5,5-dimethyl-4,6-diphenyl-5H-cyclopenta[d]pyrimidine 4.4g (13.4mmol), Pd ₂ (dba) ₃ 0.6g ( 5 mol%), 0.1 g (0.6 mmol) of tri- tert -butylphosphine, and 3.5 g (36.4 mmol) of sodium tert-butoxide were added to 100 ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 6.0g (7.9mmol, yield 65%) of R501, the target compound, was obtained.

GC-Mass (theoretical value: 754.92 g/mol, measured value: 754 g/mol)

[ Synthesis example 19] Synthesis of R506

Under nitrogen flow, A1 5.6g (12.1mmol), 2-chloro-4,5,6-triphenyl-5H-pyrrolo[3,2-d]pyrimidine 4.1g (13.4mmol), Pd ₂ (dba) ₃ 0.6g ( 5 mol%), 0.1 g (0.6 mmol) of tri- tert -butylphosphine, and 3.5 g (36.4 mmol) of sodium tert-butoxide were added to 100 ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 5.6 g (7.7 mmol, yield 63%) of R506, the target compound, was obtained.

GC-Mass (theoretical value: 728.84g/mol, measured value: 728g/mol)

[ Synthesis example 20] Synthesis of R511

Under nitrogen stream, A1 5.6g (12.1mmol), 2-chloro-4,6-diphenylfuro[3,2-d]pyrimidine 5.1g (13.4mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), tri - 0.1g (0.6mmol) of tert -butylphosphine and 3.5g (36.4mmol) of sodium tert-butoxide were added to 100ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 6.1g (7.5mmol, yield 62%) of R511, the target compound, was obtained.

GC-Mass (theoretical value: 803.95 g/mol, measured value: 803 g/mol)

[ Synthesis example 21] Synthesis of R521

Under a nitrogen stream, A12 5.0g (12.1mmol), 2-chloro-5,5-dimethyl-4,6-diphenyl-5H-cyclopenta[d]pyrimidine 4.4g (13.4mmol), Pd ₂ (dba) ₃ 0.6g ( 5 mol%), 0.1 g (0.6 mmol) of tri- tert -butylphosphine, and 3.5 g (36.4 mmol) of sodium tert-butoxide were added to 100 ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 5.6 g (7.9 mmol, yield 65%) of R521, the target compound, was obtained.

GC-Mass (theoretical value: 705.89 g/mol, measured value: 705 g/mol)

[ Synthesis example 22] Synthesis of R522

Under a nitrogen stream, A12 5.0g (12.1mmol), 2-chloro-4,5,6-triphenyl-5H-pyrrolo[3,2-d]pyrimidine 4.1g (13.4mmol), Pd ₂ (dba) ₃ 0.6g ( 5 mol%), 0.1 g (0.6 mmol) of tri- tert -butylphosphine, and 3.5 g (36.4 mmol) of sodium tert-butoxide were added to 100 ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 5.2g (7.7mmol, yield 63%) of R522, the target compound, was obtained.

GC-Mass (theoretical value: 679.81 g/mol, measured value: 679 g/mol)

[ Synthesis example 23] Synthesis of R523

Under nitrogen stream, A12 5.0g (12.1mmol), 2-chloro-4,6-diphenylfuro[3,2-d]pyrimidine 4.3g (13.4mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), tri - 0.1g (0.6mmol) of tert -butylphosphine and 3.5g (36.4mmol) of sodium tert-butoxide were added to 100ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 5.7g (7.5mmol, yield 62%) of R523, the target compound, was obtained.

GC-Mass (theoretical value: 754.92 g/mol, measured value: 754 g/mol)

[ Synthesis example 24] Synthesis of R524

Under nitrogen stream, A13 4.7g (11.8mmol), 2-chloro-5,5-dimethyl-4,6-diphenyl-5H-cyclopenta[d]pyrimidine 4.3g (13.0mmol), Pd ₂ (dba) ₃ 0.6g ( 5 mol%), 0.1 g (0.6 mmol) of tri- tert -butylphosphine, and 3.4 g (35.4 mmol) of sodium tert-butoxide were added to 100 ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 5.3g (7.7mmol, yield 65%) of R524, the target compound, was obtained.

GC-Mass (theoretical value: 695.87g/mol, measured value: 695g/mol)

[ Synthesis example 25] Synthesis of R527

Under a nitrogen stream, A14 4.5g (11.8mmol), 2-chloro-5,5-dimethyl-4,6-diphenyl-5H-cyclopenta[d]pyrimidine 4.3g (13.0mmol), Pd ₂ (dba) ₃ 0.6g ( 5 mol%), 0.1 g (0.6 mmol) of tri- tert -butylphosphine, and 3.4 g (35.4 mmol) of sodium tert-butoxide were added to 100 ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 5.2g (7.7mmol, yield 65%) of R527, the target compound, was obtained.

GC-Mass (theoretical value: 679.81 g/mol, measured value: 679 g/mol)

[ Synthesis example 26] Synthesis of R530

A15 6.5g under nitrogen stream (12.1mmol), 2-chloro-5,5-dimethyl-4,6-diphenyl-5H-cyclopenta[d]pyrimidine 4.4g (13.4mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), tri - 0.1g (0.6mmol) of tert -butylphosphine and 3.5g (36.4mmol) of sodium tert-butoxide were added to 100ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 6.5 g (7.9 mmol, yield 65%) of R530, the target compound, was obtained.

GC-Mass (theoretical value: 828.01g/mol, measured value: 828g/mol)

[ Synthesis example 27] Synthesis of R533

Under nitrogen stream, A16 5.2g (12.0mmol), 2-chloro-5,5-dimethyl-4,6-diphenyl-5H-cyclopenta[d]pyrimidine 4.4g (13.2mmol), Pd ₂ (dba) ₃ 0.6g ( 5 mol%), 0.1 g (0.6 mmol) of tri- tert -butylphosphine, and 3.5 g (35.9 mmol) of sodium tert-butoxide were added to 100 ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 5.7g (7.8mmol, yield 65%) of R533, the target compound, was obtained.

GC-Mass (theoretical value: 727.94 g/mol, measured value: 727 g/mol)

[ Synthesis example 28] Synthesis of R536

Under nitrogen stream, A17 4.9g (12.1mmol), 2-chloro-5,5-dimethyl-4,6-diphenyl-5H-cyclopenta[d]pyrimidine 4.4g (13.4mmol), Pd ₂ (dba) ₃ 0.6g ( 5 mol%), 0.1 g (0.6 mmol) of tri- tert -butylphosphine, and 3.5 g (36.4 mmol) of sodium tert-butoxide were added to 100 ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 5.5 g (7.9 mmol, yield 65%) of R536, the target compound, was obtained.

GC-Mass (theoretical value: 695.81g/mol, measured value: 695g/mol)

[ Synthesis example 29] Synthesis of R539

Under a nitrogen stream, A18 6.1g (12.1mmol), 2-chloro-5,5-dimethyl-4,6-diphenyl-5H-cyclopenta[d]pyrimidine 4.4g (13.4mmol), Pd ₂ (dba) ₃ 0.6g ( 5 mol%), 0.1 g (0.6 mmol) of tri- tert -butylphosphine, and 3.5 g (36.4 mmol) of sodium tert-butoxide were added to 100 ml of toluene and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 6.3g (7.9mmol, yield 65%) of R539, the target compound, was obtained.

GC-Mass (theoretical value: 797.00g/mol, measured value: 797g/mol)

[ Synthesis example 30] Synthesis of R541

Under nitrogen flow, A1 5.6g (12.1mmol), 5-chloro-1,7-diphenyl-1H-pyrazolo[4,3-d]pyrimidine 4.1g (13.4mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), 0.1g (0.6mmol) of tri- tert -butylphosphine, and 3.5g (36.4mmol) of sodium tert-butoxide were added to 100ml of Toluenel and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 5.8 g (7.9 mmol, yield 65%) of R541, the target compound, was obtained.

GC-Mass (theoretical value: 728.84g/mol, measured value: 728g/mol)

[ Synthesis example 31] Synthesis of R561

Under nitrogen stream, A1 5.6g (12.1mmol), 5-chloro-2,7-diphenyloxazolo[5,4-d]pyrimidine 4.1g (13.4mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), 0.1g (0.6mmol) of tri- tert -butylphosphine, and 3.5g (36.4mmol) of sodium tert-butoxide were added to 100ml of Toluenel and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 5.8g (7.9mmol, yield 65%) of R561, the target compound, was obtained.

GC-Mass (theoretical value: 729.82g/mol, measured value: 729g/mol)

[ Synthesis example 32] Synthesis of R581

Under nitrogen air flow, A1 5.6g (12.1mmol), 2-chloro-6,7,8-triphenyl-7H-purine 5.1g (13.4mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), 0.1g (0.6mmol) of tri- tert -butylphosphine, and 3.5g (36.4mmol) of sodium tert-butoxide were added to 100ml of Toluenel and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 6.4g (7.9mmol, yield 65%) of R581, the target compound, was obtained.

GC-Mass (theoretical value: 804.94g/mol, measured value: 804g/mol)

[ Synthesis example 33] Synthesis of R551

Under nitrogen stream, A12 5.0g (12.1mmol), 5-chloro-1,7-diphenyl-1H-pyrazolo[4,3-d]pyrimidine 4.1g (13.4mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), 0.1g (0.6mmol) of tri- tert -butylphosphine, and 3.5g (36.4mmol) of sodium tert-butoxide were added to 100ml of Toluenel and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 5.4 g (7.9 mmol, yield 65%) of R551, the target compound, was obtained.

GC-Mass (theoretical value: 679.81 g/mol, measured value: 679 g/mol)

[ Synthesis example 34] Synthesis of R571

Under nitrogen stream, A12 5.0g (12.1mmol), 5-chloro-2,7-diphenyloxazolo[5,4-d]pyrimidine 4.1g (13.4mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), 0.1g (0.6mmol) of tri- tert -butylphosphine, and 3.5g (36.4mmol) of sodium tert-butoxide were added to 100ml of Toluenel and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 5.2g (7.7mmol, yield 63%) of R571, the target compound, was obtained.

GC-Mass (theoretical value: 680.79 g/mol, measured value: 680 g/mol)

[ Synthesis example 35] Synthesis of R591

Under nitrogen air flow, A12 5.0g (12.1mmol), 2-chloro-6,8,9-triphenyl-9H-purine 5.1g (13.4mmol), Pd ₂ (dba) ₃ 0.6g (5 mol%), tri- tert -Butylphosphine 0.1g (0.6mmol) and Sodium tert-butoxide 3.5g (36.4mmol) were added to 100ml of Toluenel and stirred at 110°C for 4 hours. After the reaction was completed, the organic layer was separated with methylene chloride and water was removed using MgSO ₄ . Purified by column chromatography, 5.7g (7.5mmol, yield 62%) of R591, the target compound, was obtained.

GC-Mass (theoretical value: 755.91 g/mol, measured value: 755 g/mol)

[ Synthesis example 36] Synthesis of R601

Under a nitrogen stream, A19 9.2g (12.1 mmol), 2-bromo-4,6-diphenylthieno[3,2-d]pyrimidine 5.3g (14.5 mmol), Pd(PPh ₃ ) ₄ 0.7g (5 mol%) and potassium 7.0 g (36.3 mmol) of carbonate was added to Toluene/H ₂ O/Ethanol 80ml/40ml/40ml and stirred at 110°C for 3 hours. After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, R601 (8.7 g, 12.1 mmol, yield 72%).

GC-Mass (theoretical value: 999.19g/mol, measured value: 999g/mol)

[ Synthesis example 37] Synthesis of R602

Under a nitrogen stream, A19 7.8g (11.8 mmol), 2-bromo-4,6-diphenylthieno[3,2-d]pyrimidine 5.2g (14.2 mmol), Pd(PPh ₃ ) ₄ 0.7g (5 mol%) and potassium 4.9 g (35.4 mmol) of carbonate was added to 80ml/40ml/40ml of Toluene/H ₂ O/Ethanol and stirred at 110°C for 3 hours. After completion of the reaction, the organic layer was separated using methylene chloride and water was removed using MgSO ₄ . After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, R602 (7.6 g, 8.5 mmol, yield 72%).

GC-Mass (theoretical value: 900.10 g/mol, measured value: 900 g/mol)

[ Example 1 to 31] red organic electric field Fabrication of light emitting devices

The compound synthesized in the above synthesis example was purified by sublimation to high purity by a commonly known method, and then a red organic electroluminescent device was manufactured according to the process below.

First, a glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1500 Å was ultrasonically cleaned with distilled water. After cleaning, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, methanol, etc., drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then cleaning the glass substrate using UV for 5 minutes and using a vacuum evaporator. The glass substrate was transferred to .

On the ITO glass substrate (electrode) prepared in this way, m-MTDATA (60 nm)/TCTA (80 nm)/ 90% each compound synthesized in Synthesis Examples 1 to 29, 36, and 37 + 10% (piq) ₂ Ir(acac) ) (300 nm)/BCP (10 nm)/Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm) were stacked in that order to produce an organic electroluminescent device.

[ Comparative example One]

A red organic electroluminescent device was manufactured in the same process as Example 1, except that CBP was used instead of compound R41 as the light-emitting host material.

[ Comparative example 2]

A red organic electroluminescent device was manufactured in the same process as Example 1, except that D1 was used instead of compound R41 as the light-emitting host material.

The structures of m-MTDATA, TCTA, (piq) ₂ Ir(acac), BCP, Alq ₃ , CBP and D1 used are as follows.

[ Evaluation example One]

For each organic electroluminescent device manufactured in Examples 1 to 31 and Comparative Examples 1 and 2, the driving voltage, emission peak, and current efficiency were measured at a current density of 10 mA/cm2, and the results are shown in Table 1 below. It was.

Sample luminous layer host Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 1 R41 4.0 621 17.5 Example 2 R42 4.3 621 17.4 Example 3 R43 4.1 621 16.8 Example 4 R44 4.5 621 17.2 Example 5 R45 4.5 621 16.5 Example 6 R484 4.3 621 17.2 Example 7 R281 4.2 621 16.8 Example 8 R283 4.3 621 17.2 Example 9 R284 4.4 621 17.4 Example 10 R300 4.3 621 16.8 Example 11 R299 4.2 621 17.2 Example 12 R496 4.5 621 16.1 Example 13 R485 4.2 621 15.8 Example 14 R491 4.2 621 15.9 Example 15 R121 4.1 621 16.3 Example 16 R181 4.4 621 18.7 Example 17 R498 4.3 621 17.2 Example 18 R501 4.4 621 16.1 Example 19 R506 4.1 621 16.7 Example 20 R511 4.2 621 18.3 Example 21 R521 3.3 621 15.9 Example 22 R522 3.5 621 14.8 Example 23 R523 3.3 621 15.7 Example 24 R524 3.5 621 15.2 Example 25 R527 3.3 621 14.8 Example 26 R530 3.5 623 15.0 Example 27 R533 3.0 621 14.5 Example 28 R536 3.6 621 14.5 Example 29 R539 3.3 621 15.1 Example 30 R601 3.5 621 14.2 Example 31 R602 3.5 621 14.5 Comparative Example 1 CBP 5.7 622 9.2 Comparative example 2 D1 4.2 622 13.1

As shown in Table 1, when the compound according to the present invention was used as a material for the light-emitting layer of a red organic electroluminescent device (Examples 1 to 31), when conventional CBP was used as a material for the light-emitting layer of a red organic electroluminescent device (compare It was found that the efficiency and driving voltage were superior to those in Example 1), and the efficiency was found to be superior to that in the case where D1 was used as the light emitting layer material of the red organic electroluminescent device (Comparative Example 2).

[ Example 32 to 35] Organic electric field Fabrication of light emitting devices

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1500 Å was ultrasonically cleaned with distilled water. After cleaning, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, methanol, etc., drying, transfer to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then cleaning the glass substrate for 5 minutes using UV. Afterwards, the glass substrate was transferred to a vacuum laminate.

On the ITO glass substrate (electrode) prepared as above, m-MTDATA (60nm)/each compound synthesized in Synthesis Examples 4, 9, 26, and 28 (80nm)/DS-H522 + 5% DS-501 (300nm)/ An organic electroluminescent device was manufactured by stacking BCP (10nm)/Alq3 (30 nm)/LiF (1nm)/Al (200nm) in this order.

[ Comparative example 3]

An organic electroluminescent device was manufactured in the same process as Example 32, except that NPB was used instead of the compound of Synthesis Example 4 used as the material for the hole transport layer.

The DS-H522 and DS-501 used are products of Doosan Electronics BG, and the structure of the NPB is as follows.

[ Evaluation example 2]

The driving voltage and current efficiency were measured at a current density of 10 mA/cm2 for each organic electroluminescent device manufactured in Examples 32 to 35 and Comparative Example 3, and the results are shown in Table 2 below.

Sample hole transport layer Driving voltage (V) Current efficiency (cd/A) Example 32 R44 3.0 21.9 Example 33 R284 2.8 22.5 Example 34 R530 3.6 35.7 Example 35 R536 3.7 33.9 Comparative Example 3 NPB 5.3 18.1

As shown in Table 2, when the compound according to the present invention was used as a hole transport layer material of an organic electroluminescent device (Examples 32 to 35), when conventional NPB was used as a hole transport layer material of an organic electroluminescent device (Comparative Example 3), it was found that the efficiency and driving voltage were superior.

[ Example 36 to 42] blue organic electric field Fabrication of light emitting devices

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

DS-205 (80 nm)/NPB (15 nm)/ADN + 5% DS-405 (30nm)/ each compound synthesized in Synthesis Examples 20, 30 to 35 on the ITO glass substrate (electrode) prepared as above / An organic electroluminescent device was manufactured by stacking LiF (1 nm)/Al (200 nm) in that order.

[ Comparative example 4] Blue Organic electric field Fabrication of light emitting devices

An organic electroluminescent device was manufactured in the same process as Example 36, except that Alq ₃ was used instead of the compound of Synthesis Example 20 as the material for the electron transport layer and deposited to 30 nm.

The DS-205 and DS-405 used are products of Doosan Electronics BG, and the structure of the ADN is as follows.

[ Evaluation example 3]

The driving voltage, current efficiency, and luminescence peak at a current density of 10 mA/cm2 were measured for each organic electroluminescent device manufactured in Examples 36 to 42 and Comparative Example 4, and the results are shown in Table 3 below.

Sample electron transport layer Driving voltage (V) Current efficiency (cd/A) Emission peak (nm) Example 36 R511 3.5 10.8 458 Example 37 R541 3.2 8.8 458 Example 38 R561 3.2 9.4 458 Example 39 R581 3.8 9.9 458 Example 40 R551 3.1 8.5 458 Example 41 R571 3.3 8.8 458 Example 42 R591 3.6 9.1 459 Comparative Example 4 Alq ₃ 5.2 5.4 458

As shown in Table 3, when the compound according to the present invention was used as an electron transport layer material of an organic electroluminescent device (Examples 36 to 42), when it was used as a hole transport layer material of an organic electroluminescent device using conventional Alq ₃ (Examples 36 to 42) It was found that efficiency and driving voltage were superior to Comparative Example 4).

Claims (8)

Compounds represented by Formula 6 or Formula 7:
[Formula 6]

[Formula 7]

In Formula 6 or Formula 7,
A is a 5-membered ring containing or not containing one atom of S, O and N,
At this time, the 5-membered ring of A is substituted with an aryl group of C ₆ to C ₆₀ ,
Ar ₁ is selected from the group consisting of hydrogen, an aryl group having C ₆ to C ₆₀ and a heteroaryl group having 5 to 60 nuclear atoms,
L ₁ and L ₂ are the same as or different from each other, and are each independently selected from the group consisting of a single bond, an arylene group of C ₆ to C ₁₈ , and a heteroarylene group of 5 to 18 nuclear atoms,
_{X 3 and _ _ _ _} , except for the case where both X ₃ and X ₄ are single bonds,
Y ₅ to Y ₈ and Y ₁₁ to Y ₁₈ are each independently CR ₇ , wherein a plurality of R ₇ is the same or different from each other,
R ₄ to R ₇ are the same or different from each other, and are each independently 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, or are combined with adjacent groups to form a condensed aromatic ring or Forms a condensed heteroaromatic ring,
The aryl group and heteroaryl group of Ar ₁ , the arylene group and heteroarylene group of L ₁ and L ₂ , and the aryl group and heteroaryl group of R ₄ to R ₇ are each independently selected from deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group with 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 ₂ ~C ₄₀ alkyl boron group, C ₆ Substituted with one or more substituents selected from the group consisting of an aryl boron group of ~C ₆₀ , an arylphosphine group of C ₆ ~ C ₆₀ , an arylphosphine oxide group of C ₆ ~ C ₆₀ , and an arylamine group of C ₆ ~ C ₆₀ or It is unsubstituted, and when the substituents are plural, they may be the same or different from each other. delete delete delete According to paragraph 1,
In Formula 6 or Formula 7,

A compound in which the moiety represented by is selected from the group consisting of moieties represented by S-1 to S-8 below.

An organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode,
An organic electroluminescent device wherein at least one of the one or more organic material layers includes the compound according to claim 1 or 5. According to clause 6,
The organic material layer containing the compound is an organic electroluminescent device selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a light emitting layer. According to clause 6,
An organic electroluminescent device in which the organic material layer containing the compound is a phosphorescent layer.