KR102633649B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device containing the same. The compound according to the present invention is applied to an organic material layer of an organic electroluminescent device, preferably a light emitting layer material, a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer. As it is used, the luminous efficiency, driving voltage, and lifespan of the organic electroluminescent device can be improved.

Description

Organic compounds and organic electroluminescent devices containing the same {ORGANIC COMPOUNDS AND ORGANIC ELECTRO LUMINESCENCE DEVICE COMPRISING THE SAME}

The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescent device and an organic electroluminescent device containing the same.

Beginning with the observation of organic thin film luminescence by Bernanose in the 1950s, research on organic electroluminescent (EL) devices continued, leading to blue electroluminescence using anthracene single crystals in 1965, and Tang in 1987. ) presented an organic electroluminescent device with a layered structure divided into a functional layer of a hole layer and a light-emitting layer. 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.

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. 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.

Light-emitting materials can be divided into blue, green, and red light-emitting materials according to their emission color, and yellow and orange light-emitting materials to achieve 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. At this time, because the development of phosphorescent materials can theoretically improve luminous efficiency by up to four times compared to fluorescence, much research is being conducted on phosphorescent host materials as well as phosphorescent dopants.

So far, hole injection layer and hole transport layer. NPB, BCP, Alq ₃ , etc. are widely known as hole blocking layer and electron transport layer materials, and anthracene derivatives are reported as light emitting layer materials. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy) ₃ , and (acac)Ir(btp) ₂ , which have advantages in terms of efficiency improvement among light emitting layer materials, produce blue, green, and red colors. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

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However, although conventional organic layer materials have advantages in terms of luminescence characteristics, their glass transition temperature is low and thermal stability is very poor, so they are not at a satisfactory level in terms of the lifespan of organic electroluminescent devices. Therefore, the development of organic layer materials with excellent performance is required.

In order to solve the above problems, the purpose of the present invention is to provide a new compound that can improve the efficiency, lifespan, and stability of an organic electroluminescent device and an organic electroluminescent device using the compound.

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

[Formula 1]

In Formula 1,

p and q are each independently integers from 0 to 4;

L ₁ and L ₂ 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 ₁ to X ₇ are each independently N or C(R ₃ ), but at least one of X ₁ to X ₇ is N;

R ₁ and R ₂ are each independently selected from deuterium, halogen, cyano group, nitro 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, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ 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 is selected from the group consisting of an arylphosphine group, a C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and a C ₆ ~ C ₆₀ arylamine group, and when each of R ₁ and R ₂ is plural, they are the same or different from each other and;

R ₃ is hydrogen, deuterium, halogen, cyano group, nitro 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, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , aryloxy group with C ₆ to C ₆₀ , C ₃ ~ 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 mono or diarylphosphinyl group, and C ₆ ~ C ₆₀ arylamine group, and when there are more than one R ₃ , they are the same or different from each other;

The arylene group and heteroarylene group of L ₁ and L ₂ , and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, and heterocycloalkyl group of R ₁ to R ₃ , arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group , C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl 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 mono or diarylphosphinyl group and C ₆ ~ C ₆₀ is substituted or unsubstituted with one or more substituents selected from the group consisting of arylsilyl groups, and when substituted with a plurality of substituents, these may be the same or different from each other.

The present invention provides an organic electroluminescent device 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 of Formula 1. .

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

In the present invention, “alkenyl” is 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 double bond, examples of which include vinyl, Examples include allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

In the present invention, “alkynyl” is 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 which include ethynyl. , 2-propynyl, etc., but is 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 of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

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 in the ring, preferably 1 to 3 carbons, 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 it is further interpreted to include a condensed form with an aryl group. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Polycyclics such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; Examples include 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 means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, where R' means 1 to 40 alkyl, and has a linear, branched or cyclic structure. It is interpreted as including. Examples of such 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.

“Cycloalkyl” in the present invention 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, preferably 1 to 3 carbons in the ring, is N, O, It is substituted with a hetero atom such as S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

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 5 to 60 carbon atoms.

“Condensed ring” in the present invention means a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.

Since the compound represented by Formula 1 according to the present invention has excellent thermal stability, hole transport, hole injection performance, electron transport and electron injection performance, and has excellent phosphorescence properties as a light emitting layer, it is preferably used as an organic material layer material of an organic electroluminescent device. Can be used as a light emitting layer material, a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer.

In addition, the new compound represented by Formula 1 of the present invention, when used as a light-emitting layer material, a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer, has excellent luminescence performance, low driving voltage, high efficiency, and long life compared to conventional materials. It is possible to manufacture an organic electroluminescent device having an organic electroluminescent device, and furthermore, a full-color display panel with greatly improved performance and lifespan can be manufactured.

Hereinafter, the present invention will be described in detail.

1. Novel organic compounds

The new organic compound according to the present invention is a heteroaryl containing N such as a quinazoline or quinoline moiety in triphenylene, various linkers (carbazole, dibenzothiophene, dibenzofuran, fluorene, spirofluorene, It forms a basic skeleton linked with acridine, cyanthrene, dibenzodioxene, phenoxacin, phenyl, biphenyl, naphthalene, phenanthrene, etc.). Specifically, it is characterized as a compound represented by the following formula (1):

[Formula 1]

In Formula 1,

p and q are each independently integers from 0 to 4;

L ₁ and L ₂ 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 ₁ to X ₇ are each independently N or C(R ₃ ), but at least one of X ₁ to X ₇ is N;

R ₁ and R ₂ are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl 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 ₆ to 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 ₃ ~ 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 is selected from the group consisting of an arylphosphine group, a C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and a C ₆ ~ C ₆₀ arylamine group, and when each of R ₁ and R ₂ is plural, they are the same or different from each other and;

R ₃ is hydrogen, deuterium, halogen, cyano group, nitro 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, aryl group with C ₆ to C ₆₀ , heteroaryl group with 5 to 60 nuclear atoms, alkyloxy group with C ₁ to C ₄₀ , aryloxy group with C ₆ to C ₆₀ , C ₃ ~ 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 mono or diarylphosphinyl group, and C ₆ ~ C ₆₀ arylamine group, and when there are more than one R ₃ , they are the same or different from each other;

The arylene group and heteroarylene group of L ₁ and L ₂ , and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, and heterocycloalkyl group of R ₁ to R ₃ , arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group , C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl 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 mono or diarylphosphinyl group and C ₆ ~ C ₆₀ is substituted or unsubstituted with one or more substituents selected from the group consisting of arylsilyl groups, and when substituted with a plurality of substituents, these may be the same or different from each other.

The compound represented by Formula 1 has a higher molecular weight than conventional materials for organic electroluminescent devices [e.g., 4,4-dicarbazolylbiphenyl (hereinafter referred to as 'CBP')], and the triphenylene group has a glass transition Not only does it have excellent thermal stability due to its high temperature, but it also has a wide energy band gap, so it can be widely applied in organic light-emitting devices as a phosphorescent host material, hole injection material, hole transport, electron injection, electron transport, and light-emitting layer material.

The present invention relates to triphenylene with electronic properties and linkers with hole properties (carbazole, dibenzothiophene, dibenzofuran, fluorene, spirofluorene, acridine, thianthrene, dibenzodioxene, A hybrid compound containing a derivative (phenoxacin, etc.), the compound of Formula 1 is added to any one of the organic layers of the organic electroluminescent device: a light emitting layer, an electron injection layer, an electron transport layer, a hole transport layer, and a hole injection layer. When used as a material, the driving voltage, efficiency, and lifespan of the device can be improved.

More specifically, the compound of Formula 1 according to the present invention can control HOMO and LUMO energy levels depending on the types of various linkers introduced into the basic skeleton.

For example, in the compound of Formula 1, when an electron donating group (EDG) with a large electron donation, such as a carbazole group or a terphenyl group, is bonded to the basic skeleton, hole injection and transport are performed smoothly, thereby enabling hole injection. It can also be usefully used as a layer/transport layer or light-emitting auxiliary layer material.

The compound of Formula 1 can improve the emission characteristics of an organic electroluminescent device, as well as hole injection/transport ability, electron injection/transport ability, luminous efficiency, driving voltage, and lifespan characteristics.

In addition, the compound of Formula 1 has an electron withdrawing group (EWG) with high electron absorption, such as a nitrogen-containing heterocycle (e.g., quinazoline, quinoline, etc.) bonded to the basic skeleton, so the entire molecule is bipolar. Because it has the characteristics of, it can increase the bonding force between holes and electrons.

The compound of Formula 1 can improve the emission characteristics of an organic electroluminescent device and at the same time improve hole injection/transport ability, electron injection/transport ability, luminous efficiency, driving voltage, and lifespan characteristics. Therefore, the compound of Formula 1 according to the present invention is an organic layer material of an organic electroluminescent device, preferably a light-emitting layer material (green and/or red phosphorescent host material), an electron transport layer/injection layer material, a hole transport layer/injection layer material, It can be used as a light emitting auxiliary layer material and a lifespan improvement layer material, more preferably as a light emitting layer material, an electron injection layer material, a light emitting auxiliary layer material, or a lifespan improvement layer material.

According to a preferred embodiment of the present invention, the compound represented by Formula 1 may be specifically a compound represented by Formula 2 or 3 below:

[Formula 2]

[Formula 3]

In Formulas 2 and 3,

l is an integer from 0 to 4;

m is an integer from 0 to 3;

R ₄ and R ₅ are each independently deuterium, halogen, cyano group, nitro 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, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ 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 is selected from the group consisting of an arylphosphine group, a C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and a C ₆ ~ C ₆₀ arylamine group, and when each of R ₄ and R ₅ is plural, they are the same or different from each other. and;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, aryl group of R ₄ and R ₅ Boron group, arylphosphine group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ Arylamine group of C ₆₀ , cycloalkyl group of C ₃ ~ C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, alkylsilyl group of C ₁ ~ C ₄₀ , alkyl boron group of C ₁ ~ C ₄₀ , C ₆ ~ Substituted with one or more substituents selected from the group consisting of C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and C ₆ ~ C ₆₀ arylsilyl group. When substituted or unsubstituted and substituted with a plurality of substituents, they are the same or different from each other;

p, q, R ₁ , R ₂ , L ₁ , L ₂ and X ₁ to X ₇ are as defined in Formula 1 above.

According to a preferred embodiment of the present invention, the compound represented by Formula 1 may be specifically a compound represented by any one of the following 4 to 13:

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

In Formulas 4 to 13,

l is an integer from 0 to 4;

m is an integer from 0 to 3;

R ₄ and R ₅ are each independently deuterium, halogen, cyano group, nitro 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, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Aryloxy group, C ₃ ~ 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 is selected from the group consisting of an arylphosphine group, a C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and a C ₆ ~ C ₆₀ arylamine group, and when each of R ₄ and R ₅ is plural, they are the same or different from each other. and;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, aryl group of R ₄ and R ₅ Boron group, arylphosphine group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ Arylamine group of C ₆₀ , cycloalkyl group of C ₃ ~ C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, alkylsilyl group of C ₁ ~ C ₄₀ , alkyl boron group of C ₁ ~ C ₄₀ , C ₆ ~ Substituted with one or more substituents selected from the group consisting of C ₆₀ arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and C ₆ ~ C ₆₀ arylsilyl group. When unsubstituted or substituted with a plurality of substituents, they are the same or different from each other;

p, q, R ₁ to R ₃ , L ₁ and L ₂ are as defined in Formula 1 above.

According to a preferred embodiment of the present invention, L ₁ and L ₂ may each independently be a single bond or a substituent represented by any of the following formulas 14 to 19:

[Formula 14]

[Formula 15]

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

In Formulas 14 to 19,

* refers to the part where the combination takes place;

Y ₁ is O, S, Se, N(R ₆ ), C(R ₇ )(R ₈ ) or Si(R ₉ )(R ₁₀ );

Y ₂ and Y ₃ are each independently selected from the group consisting of O, S, Se, N(R ₆ ), and C(R ₇ )(R ₈ );

Y ₄ is C or Si;

X ₈ to X ₃₁ are each independently N or C(R ₁₁ );

R ₆ to R ₁₁ are each independently hydrogen, deuterium, halogen, cyano group, nitro 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, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ ~ 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 ~ It is selected from the group consisting of a C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group, and when each of R ₆ to R ₈ and R ₁₁ is plural. They may be the same or different from each other;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, aryl group of R ₆ to R ₁₁ Boron group, arylphosphine group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ Arylamine group of C ₆₀ , cycloalkyl group of C ₃ ~ C ₄₀ , heterocycloalkyl group of 3 to 40 nuclear atoms, alkylsilyl group of C ₁ ~ C ₄₀ , alkyl boron group of C ₁ ~ C ₄₀ , C ₆ ~ Substituted with one or more substituents selected from the group consisting of C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and C ₆ ~ C ₆₀ arylsilyl group. When substituted or unsubstituted and substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, L ₁ may be a single bond or a substituent represented by Formula 17, and L ₂ may be a substituent represented by any one of Formulas 14 to 19.

According to a preferred embodiment of the present invention, R ₁ to R ₃ may each independently be an aryl group having C ₆ to C ₆₀ or a heteroaryl group having 5 to 60 nuclear atoms.

According to a preferred embodiment of the present invention, R ₁ to R ₃ may each independently be selected from the group consisting of a phenyl group, a biphenyl group, a naphthalenyl group, and a substituent represented by the following formula (20):

[Formula 20]

In Formula 20,

* refers to the part where the combination takes place;

Z ₁ to Z ₅ are each independently N or C(R ₁₂ ), but at least one of Z ₁ to Z ₅ is N;

R ₁₂ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, Heteroaryl group with 5 to 60 nuclear atoms, aryloxy group with C ₆ to C ₆₀ , alkyloxy group with C ₁ to C ₄₀ , cycloalkyl group with C ₃ to C ₄₀ , heterocycloalkyl group with 3 to 40 nuclear atoms. , C ₆ ~ C ₆₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group , selected from the group consisting of a C ₆ to C ₆₀ mono or diarylphosphinyl group and a C ₆ to C ₆₀ arylsilyl group, or condensed by bonding with an adjacent group (e.g., L ₁ , another adjacent R ₁₂ ). may form a ring, and when R ₁₂ is plural, they are the same or different from each other;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group _, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, Arylphosphine group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Unsubstituted or substituted with one or more substituents selected from the group consisting of arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and C ₆ ~ C ₆₀ arylsilyl group. And when substituted with a plurality of substituents, these may be the same or different from each other.

According to a preferred embodiment of the present invention, specific examples of the substituent represented by Formula 20 include substituents represented by A-1 to A-15 below, but are not limited thereto:

delete

In the above formulas A-1 to A-15,

n is an integer from 0 to 4, and when n is 0, it means that hydrogen is not substituted by the substituent R ₁₃ , and when n is an integer from 1 to 4, R ₁₃ is deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl 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 ₆ ~C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine group, C ₁ ~C ₄₀ alkyl 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 mono or diaryl phosphine It may be selected from the group consisting of a nyl group and an arylsilyl group of C ₆ to C ₆₀ , or may be combined with an adjacent group (e.g., R ₁₂ or another R ₁₃ , etc.) to form a condensed ring, and when there are two or more R ₁₃ They may be the same or different from each other;

_The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, Arylphosphine group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Unsubstituted or substituted with one or more substituents selected from the group consisting of arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and C ₆ ~ C ₆₀ arylsilyl group. When substituted with a plurality of substituents, they may be the same or different from each other;

* and R ₁₂ are each as defined in Formula 20 above.

According to a preferred embodiment of the present invention, at least one of R ₁ to R ₃ may be a substituent represented by the following formula (21):

[Formula 21]

In Formula 21 above,

* refers to the part where the combination takes place;

L ₃ is selected from the group consisting of a single bond, an arylene group having C ₆ to C ₁₈ and a heteroarylene group having 5 to 18 nuclear atoms;

R ₁₄ and R ₁₅ are each independently selected from the group consisting of an alkyl group of C ₁ to C ₄₀ , an aryl group of C ₆ to C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, and an arylamine group of C ₆ to C ₆₀ . Alternatively, R ₁₄ and R ₁₅ may be combined to form a condensed ring;

The arylene group and heteroarylene group of L ₃ and the alkyl group, aryl group, heteroaryl group and arylamine group of R ₁₄ and R ₁₅ are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ . Alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl 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 mono or diarylphosphinyl group and C ₆ ~ C ₆₀ When substituted or unsubstituted with one or more substituents selected from the group consisting of an arylsilyl group and substituted with a plurality of substituents, these may be the same or different from each other.

According to a preferred embodiment of the present invention, in the substituent represented by Formula 21, R ₁₄ and R ₁₅ may each independently be an aryl group of C ₆ to C ₆₀ or a heteroaryl group of 5 to 60 nuclear atoms. .

According to a preferred embodiment of the present invention, in the substituent represented by Formula 21, R ₁₄ and R ₁₅ may each independently be a phenyl group, a biphenyl group, or a fluorenyl group.

The compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto.

delete

In the present invention, the compound represented by Formula 1 can be synthesized according to general synthetic methods (Chem. Rev., 60:313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995), etc.). The detailed synthesis process for the compound of the present invention will be described in detail in the synthesis examples described later.

2. Organic electroluminescent device

Meanwhile, the present invention provides an organic electroluminescent device containing a compound represented by the compounds represented by the above-mentioned formulas 1 to 8.

Specifically, 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 is It includes a compound represented by Formula 1 above. At this time, the compound represented by Formula 1 may be used alone or in a mixture of two or more.

The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer, and among these, at least one organic material layer may include the compound represented by Formula 1. Preferably, the organic layer containing the compound of Formula 1 may be a phosphorescent layer.

According to one example of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, and in this case, the host material may include the compound represented by Formula 1 above. In this way, when the compound represented by Formula 1 is included as a light-emitting layer material of an organic electroluminescent device, preferably a green phosphorescent host, the binding force between holes and electrons in the light-emitting layer increases, thereby increasing the efficiency (light emission) of the organic electroluminescent device. efficiency and power efficiency), lifespan, brightness, and driving voltage can be improved.

The structure of the organic electroluminescent device according to the present invention described above is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport 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, the hole transport layer, the light-emitting layer, the electron transport layer, and the electron injection layer may include the compound represented by Formula 1, and preferably the light-emitting layer includes the compound represented by Formula 1. You can. At this time, the compound of the present invention can be used as a phosphorescent host of the light-emitting layer. An electron injection layer may be additionally stacked on the electron transport layer.

In addition, the structure of the organic electroluminescent device of the present invention may be one in which an anode, one or more organic material layers, and a cathode are sequentially stacked, and an insulating layer or adhesive layer is inserted at the interface between the electrode and the organic material layer.

The organic electroluminescent device of the present invention uses materials and methods known in the art, except that at least one of the organic layers (e.g., a light emitting layer) includes the compound represented by Formula 1 above. It can be manufactured by forming an organic material layer and an electrode.

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.

There is no particular limitation on the substrate that can be used in the present invention, and silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, etc. can be used.

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 SnO ₂ :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 includes 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 LiO ₂ /Al, etc., but are not limited thereto.

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

5.0 g (10.0 mmol) of 2-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)triphenylene, 4,4,4',4',5,5, under nitrogen stream. 5',5'-octamethyl-2,2'-bi(1,3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf)cl ₂ , KOAc, 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane were added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A1 (3.9 g, 7.2 mmol, yield 72%).

GC-Mass (theoretical value: 546.51 g/mol, measured value: 546 g/mol)

¹ H-NMR: δ 1.23(s, 12H), 1.71(s, 6H), 7.17(d, 1H), 7.33(s, 1H), 7.53(s, 1H), 7.61(d, 1H), 7.83~ 7.86(m, 6H), 8.03(d, 1H), 8.12~8.15(m, 3H), 8.91(d, 2H), 9.12(s, 1H)

[ Preparation example 2] Synthesis of A2

5.0 g (10.0 mmol) of 1-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)triphenylene, 4,4,4',4',5,5, under nitrogen stream. 5',5'-octamethyl-2,2'-bi(1,3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf)cl ₂ , KOAc, 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane were added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A2 (3.9 g, 7.2 mmol, yield 72%).

GC-Mass (theoretical value: 546.51 g/mol, measured value: 546 g/mol)

¹ H-NMR: δ 1.23(s, 12H), 1.71(s, 6H), 7.17(d, 1H), 7.33(s, 1H), 7.53(s, 1H), 7.61(d, 1H), 7.83~ 7.87(m, 7H), 8.10~8.12(m, 4H), 8.91(d, 2H)

[ Preparation example 3] Synthesis of A3

5.8 g (10.0 mmol) of 1-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)triphenylene, 4,4,4',4',5,5, under nitrogen stream. 5',5'-octamethyl-2,2'-bi(1,3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf)cl ₂ , KOAc, 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane were added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, the product was purified by column chromatography to obtain the target compound, A3 (4.6 g, 7.4 mmol, yield 74%).

GC-Mass (theoretical value: 622.60g/mol, measured value: 622g/mol)

¹ H-NMR: δ 1.23(s, 12H), 1.71(s, 6H), 7.17(d, 1H), 7.33(s, 1H), .7.40(m, 1H), 7.52~7.53(m,4H) , 7.53(s, 1H), 7.61(d, 1H), 7.83~7.87(m, 4H), 8.03(d, 2H), 8.10~8.12(m, 3H), 8.91(d, 1H), 9.13(s) , 2H)

[ Preparation example 4] Synthesis of A4

4-bromo-6-(triphenylen-2-yl)dibenzo[b,d]thiophene 4.9 g (10.0 mmol), 4,4,4',4',5,5,5 under nitrogen stream. ',5'-octamethyl-2,2'-bi(1,3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf)cl ₂ , KOAc, 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane were added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A4 (4.0 g, 7.4 mmol, yield 74%).

GC-Mass (theoretical value: 536.49 g/mol, measured value: 536 g/mol)

¹ H-NMR: δ 1.23(s, 12H), 7.45~7.53(m,3H), 7.82~7.87(m, 4H), 8.03(d, 2H), 8.12~8.18(m, 4H), 8.40(d , 2H), 8.91(d, 1H), 9.13(s, 1H)

[ Preparation example 5] Synthesis of A5

4-bromo-6-(triphenylen-1-yl)dibenzo[b,d]thiophene 4.9 g (10.0 mmol), 4,4,4',4',5,5,5 under nitrogen stream. ',5'-octamethyl-2,2'-bi(1,3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf)cl ₂ , KOAc, 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane were added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A5 (4.0 g, 7.4 mmol, yield 74%).

GC-Mass (theoretical value: 536.49 g/mol, measured value: 536 g/mol)

¹ H-NMR: δ 1.23(s, 12H), 7.46~7.54(m, 3H), 7.82~7.87(m, 5H), 8.10~8.12(m, 4H), 8.23(d, 1H), 8.40(d) , 2H), 8.90(d, 2H)

[ Preparation example 6] Synthesis of A6

5.7 g (10.0 mmol) of 4-bromo-6-(7-phenyltriphenylen-2-yl)dibenzo[b,d]thiophene, 4,4,4',4',5, under nitrogen stream. 5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf) cl ₂ , KOAc, 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane were added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A6 (4.7 g, 7.6 mmol, yield 76%).

GC-Mass (theoretical value: 612.59 g/mol, measured value: 612 g/mol)

¹ H-NMR: δ 1.23(s, 12H), 7.41~7.51(m, 8H), 7.82~7.85(m, 2H), 8.04(d, 2H), 8.15~8.20(m, 4H), 8.40(d) , 2H), 8.90(d, 1H), 9.13(s, 2H)

[ Preparation example 7] Synthesis of A7

4.7 g (10.0 mmol) of 2-bromo-8-(triphenylen-2-yl)dibenzo[b,d]furan under nitrogen stream, 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf)cl ₂ , KOAc , 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane were added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A7 (3.8 g, 7.3 mmol, yield 73%).

GC-Mass (theoretical value: 520.42g/mol, measured value: 520g/mol)

¹ H-NMR: δ 1.23(s, 12H), 7.50(d, 1H), 7.70~7.72(m, 3H), 7.82~7.90(m, 6H), 8.01(d, 1H), 8.08~8.15(m) , 6H), 8.90(d, 2H), 9.13(s, 1H)

[ Preparation example 8] Synthesis of A8

4.7 g (10.0 mmol) of 2-bromo-8-(triphenylen-1-yl)dibenzo[b,d]furan under nitrogen stream, 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf)cl ₂ , KOAc , 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane were added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, the product was purified by column chromatography to obtain the target compound, A8 (3.8 g, 7.3 mmol, yield 73%).

GC-Mass (theoretical value: 520.42g/mol, measured value: 520g/mol)

¹ H-NMR: δ 1.23(s, 12H), 7.50(d, 1H), 7.68~7.71(m, 3H), 7.82~7.89(m, 7H), 8.08~8.12(m, 4H), 8.90(d) , 2H)

[ Preparation example 9] Synthesis of A9

5.5 g (10.0 mmol) of 2-bromo-8-(7-phenyltriphenylen-2-yl)dibenzo[b,d]furan under nitrogen stream, 4,4,4',4',5,5 ,5',5'-octamethyl-2,2'-bi(1,3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf)cl ₂ , KOAc, 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane were added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A9 (4.4 g, 7.4 mmol, yield 74%).

GC-Mass (theoretical value: 596.52g/mol, measured value: 596g/mol)

¹ H-NMR: δ 1.23 (s, 12H), 7.40 (m, 1H), 7.50 - 7.52 (m, 5H), 7.68 - 7.71 (m, 3H), 7.82 - 7.86 (m, 4H), 8.03 (d , 2H), 8.08~8.12(m, 3H), 8.90(d, 1H), 9.13(s, 2H)

[ Preparation example 10] Synthesis of A10

5.5 g (10.0 mmol) of 3-bromo-9-phenyl-6-(triphenylen-2-yl)-9H-carbazole, 4,4,4',4',5,5,5 under nitrogen stream. ',5'-octamethyl-2,2'-bi(1,3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf)cl ₂ , KOAc, 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane were added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A10 (4.4 g, 7.4 mmol, yield 74%).

GC-Mass (theoretical value: 595.54 g/mol, measured value: 595 g/mol)

¹ H-NMR: δ 1.23(s, 12H), 7.50~7.58(m, 7H), 7.75(s, 1H), 7.81~7.86(m, 5H), 8.01(s, 1H), 8.04~8.12(m) , 5H), 8.90(d, 2H), 9.15(s, 1H)

[ Preparation example 11] Synthesis of A11

5.5 g (10.0 mmol) of 3-bromo-9-phenyl-6-(triphenylen-1-yl)-9H-carbazole, 4,4,4',4',5,5,5 under nitrogen stream. ',5'-octamethyl-2,2'-bi(1,3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf)cl ₂ , KOAc, 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane were added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, the product was purified by column chromatography to obtain the target compound, A11 (4.4 g, 7.4 mmol, yield 74%).

GC-Mass (theoretical value: 595.54 g/mol, measured value: 595 g/mol)

¹ H-NMR: δ 1.23(s, 12H), 7.50~7.58(m, 7H), 7.75(s, 1H), 7.81~7.86(m, 5H), 8.01(s, 1H), 8.04~8.12(m) , 6H), 8.90(d, 2H)

[ Preparation example 12] Synthesis of A12

6.3 g (10.0 mmol) of 3-bromo-9-phenyl-6-(7-phenyltriphenylen-2-yl)-9H-carbazole, 4,4,4',4',5, under nitrogen stream. 5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf) cl ₂ , KOAc, 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane were added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, the product was purified by column chromatography to obtain the target compound, A12 (5.1 g, 7.6 mmol, yield 78%).

GC-Mass (theoretical value: 671.63g/mol, measured value: 671g/mol)

¹ H-NMR: δ 1.23(s, 12H), 7.50~7.58(m, 12H), 7.75(s, 1H), 7.81~7.86(m, 2H), 8.01(s, 1H), 8.03~8.05(m) , 3H), 8.15~8.18(m, 4H), 8.90(d, 1H), 9.13(s, 2H)

[ Preparation example 13] Synthesis of A13

3,1 g (10.0 mmol) of 2-bromotriphenylene, 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1, 3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf)cl ₂ , KOAc, 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane. was added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A13 (2.7 g, 7.5 mmol, yield 75%).

GC-Mass (theoretical value: 354.25 g/mol, measured value: 354 g/mol)

¹ H-NMR: δ 1.23(s, 12H), 7.81~7.86(m, 5H), 8.08(d, 3H), 8.90~8.91(m, 3H)

[ Preparation example 14] Synthesis of A14

3,1 g (10.0 mmol) of 1-bromotriphenylene, 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1, 3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf)cl ₂ , KOAc, 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane. was added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, the product was purified by column chromatography to obtain the target compound, A14 (2.7 g, 7.5 mmol, yield 75%).

GC-Mass (theoretical value: 354.25 g/mol, measured value: 354 g/mol)

¹ H-NMR: δ 1.23(s, 12H), 7.81~7.86(m, 6H), 8.08(d, 3H), 8.89~8.90(m, 2H)

[ Preparation example 15] Synthesis of A15

4.6 g (10.0 mmol) of 2-(3'-bromo-[1,1'-biphenyl]-4-yl)-triphenylene, 4,4,4',4',5,5 under nitrogen stream. ,5',5'-octamethyl-2,2'-bi(1,3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf)cl ₂ , KOAc, 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane were added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A15 (3.5 g, 7.0 mmol, yield 70%).

GC-Mass (theoretical value: 506.44 g/mol, measured value: 506 g/mol)

¹ H-NMR: δ 1.23(s, 12H), 7.48~7.51(m, 5H), 7.68~7.70(m, 3H), 7.81~7.86(m, 4H), 8.03(d, 1H), 8.12~8.15 (m, 3H), 8.90(d, 2H), 9.13(s, 1H)

[ Preparation example 16] Synthesis of A16

4.6 g (10.0 mmol) of 2-(3-bromophenyl)-7-phenyltriphenylene, 4,4,4',4',5,5,5',5'-octamethyl-2 under nitrogen stream. ,2'-bi(1,3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf)cl ₂ , KOAc, 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane was added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A16 (3.5 g, 7.0 mmol, yield 70%).

GC-Mass (theoretical value: 506.44 g/mol, measured value: 506 g/mol)

¹ H-NMR: δ 1.23(s, 12H), 7.40(m, 1H), 7.48~7.50(m, 6H), 7.65(s, 1H), 7.70(d, 1H), 7.81~7.82(m, 2H) ), 8.03(d, 2H), 8.12~8.15(m, 3H), 8.90(d, 1H), 9.13(s, 2H)

[ Preparation example 17] Synthesis of A17

6.2 g (10.0 mmol) of 2-(2-bromo-9,9'-spirobi[fluorene]-7-yl)triphenylene, 4,4,4',4',5,5 under nitrogen stream. ,5',5'-octamethyl-2,2'-bi(1,3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf)cl ₂ , KOAc, 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane were added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, the product was purified by column chromatography to obtain the target compound, A17 (4.9 g, 7.4 mmol, yield 74%).

GC-Mass (theoretical value: 668.63g/mol, measured value: 668g/mol)

¹ H-NMR: δ 1.23(s, 12H), 7.16~7.19(m, 5H), 7.34(d, 3H), 7.54(s, 1H), 7.62(d, 1H), 7.75~7.78(m, 8H) ), 8.03(d, 1H), 8.12~8.14(m, 3H), 8.90(d, 2H), 9.13(s, 1H)

[ Preparation example 18] Synthesis of A18

6.2 g (10.0 mmol) of 1-(2-bromo-9,9'-spirobi[fluorene]-7-yl)triphenylene, 4,4,4',4',5,5 under nitrogen stream. ,5',5'-octamethyl-2,2'-bi(1,3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf)cl ₂ , KOAc, 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane were added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, the product was purified by column chromatography to obtain the target compound, A18 (4.9 g, 7.4 mmol, yield 74%).

GC-Mass (theoretical value: 668.63g/mol, measured value: 668g/mol)

¹ H-NMR: δ 1.23(s, 12H), 7.16~7.19(m, 5H), 7.33(d, 3H), 7.53(s, 1H), 7.62(d, 1H), 7.74~7.77(m, 9H) ), 8.12~8.14(m, 3H), 8.90(d, 2H), 9.13(s, 1H)

[ Preparation example 19] Synthesis of A19

4.9 g (10.0 mmol) of 2-bromo-8-(triphenylen-2-yl)dibenzo[b,e][1,4]dioxin, 4,4,4',4', under nitrogen stream. 5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd ( dppf)cl ₂ , KOAc, 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane were added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, the product was purified by column chromatography to obtain the target compound, A19 (3.9 g, 7.2 mmol, yield 72%).

GC-Mass (theoretical value: 536.42 g/mol, measured value: 536 g/mol)

¹ H-NMR: δ 1.23(s, 12H), 7.08~7.16(m, 3H), 7.43~7.45(m, 3H), 7.82~7.85(m, 4H), 8.05(d, 1H), 8.12~8.14 (m, 3H), 8.90(d, 2H), 9.13(s, 1H)

[ Preparation example 20] Synthesis of A20

5.2 g (10.0 mmol) of 1-bromo-9-(triphenylen-2-yl)thianthrene, 4,4,4',4',5,5,5',5'-octamethyl under nitrogen stream. -2,2'-bi(1,3,2-dioxabororane), 3.1 g (12.0 mmol), 0.3 g (5 mol%) of Pd(dppf)cl ₂ , KOAc, 3.0 g (30.0 mmol) ) and 100 ml of 1,4-dioxane were added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, it was purified by column chromatography to obtain the target compound, A20 (4.2g, 7.4mmol, yield 74%).

GC-Mass (theoretical value: 568.56g/mol, measured value: 568g/mol)

¹ H-NMR: δ 1.23(s, 12H), 7.00~7.03(m, 2H), 7.15~7.29(m, 4H), 7.82~7.85(m, 4H), 8.05(d, 1H), 8.12~8.14 (m, 3H), 8.90(d, 2H), 9.13(s, 1H)

[ Preparation example 21] Synthesis of A21

5.9 g (10.0 mmol) of 2-bromo-9,9-dimethyl-10-phenyl-7-(triphenylen-2-yl)-9,10-dihydroacridine, 4,4, under nitrogen stream. 4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxabororane), 3.1g (12.0 mmol), 0.3g (5 mol%) of Pd(dppf)cl ₂ , KOAc, 3.0 g (30.0 mmol) and 100 ml of 1,4-dioxane were added and stirred at 130°C for 5 hours.

After removing the solvent of the organic layer, the product was purified by column chromatography to obtain the target compound, A21 (4.7 g, 7.4 mmol, yield 74%).

GC-Mass (theoretical value: 637.62g/mol, measured value: 637g/mol)

¹ H-NMR: δ 1.23(s, 12H), 1.70(s, 6H), 6.61~6.64(m, 4H), 6.81(m, 1H), 7.05(s, 1H), 7.25~7.31(m, 4H) ), 7.58(s, 1H), 7.82~7.85(m, 4H), 8.05(d, 1H), 8.12~8.14(m, 3H), 8.90(d, 2H), 9.13(s, 1H)

[ Synthesis example 1] Synthesis of R1

3.9 g (7.2 mmol) of A1, 2-chloro-4-phenylquinazoline, 2.6 g (10.8 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.4 g (7.2 mmol) under nitrogen flow. , 4.7 g (14.4 mmol) of cesium carbonate and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, R1 (3.2 g, 5.2 mmol, yield 72%).

GC-Mass (theoretical value: 624.77 g/mol, measured value: 624 g/mol)

[ Synthesis example 2] Synthesis of R4

Under a nitrogen stream, 3.9 g (7.2 mmol) of A1, 6-chloro-8-phenylquinoline, 2.6 g (10.8 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.4 g (7.2 mmol), Cesium carbonate, 4.7 g (14.4 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R4 (3.2 g, 5.2 mmol, yield 72%).

GC-Mass (theoretical value: 623.78g/mol, measured value: 623g/mol)

[ Synthesis example 3] Synthesis of R5

3.9 g (7.2 mmol) of A1, 2-chloro-4-(pyridin-4-yl)quinazoline, 2.6 g (10.8 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.4g (7.2 mmol), cesium carbonate, 4.7g (14.4 mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, R5 (3.3 g, 5.3 mmol, yield 74%).

GC-Mass (theoretical value: 625.76g/mol, measured value: 625g/mol)

[ Synthesis example 4] Synthesis of R6

3.9 g (7.2 mmol) of A2, 6-chloro-8-phenylquinoline, 2.6 g (10.8 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.4 g (7.2 mmol), under nitrogen stream. Cesium carbonate, 4.7 g (14.4 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, R6 (3.2 g, 5.2 mmol, yield 71%).

GC-Mass (theoretical value: 624.77 g/mol, measured value: 624 g/mol)

[ Synthesis example 5] Synthesis of R9

3.9 g (7.2 mmol) of A2, 6-chloro-8-phenylquinoline, 2.6 g (10.8 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.4 g (7.2 mmol), under nitrogen stream. Cesium carbonate, 4.7 g (14.4 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R9 (3.2 g, 5.2 mmol, yield 72%).

GC-Mass (theoretical value: 623.78g/mol, measured value: 623g/mol)

[ Synthesis example 6] Synthesis of R10

3.9 g (7.2 mmol) of A2, 2-chloro-4-(pyridin-4-yl)quinazoline, 2.6 g (10.8 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.4g (7.2 mmol), cesium carbonate, 4.7g (14.4 mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R10 (3.3 g, 5.3 mmol, yield 74%).

GC-Mass (theoretical value: 625.76g/mol, measured value: 625g/mol)

[ Synthesis example 7] Synthesis of R11

4.6 g (7.4 mmol) of A3, 2-chloro-4-phenylquinazoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.4 mmol) under nitrogen flow. , 4.8 g (14.8 mmol) of cesium carbonate and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R11 (3.6 g, 5.2 mmol, yield 70%).

GC-Mass (theoretical value: 700.87g/mol, measured value: 700g/mol)

[ Synthesis example 8] Synthesis of R14

4.6 g (7.4 mmol) of A3, 6-chloro-8-phenylquinoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.4 mmol), under nitrogen flow. Cesium carbonate, 4.8 g (14.8 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, R14 (3.6 g, 5.2 mmol, yield 70%).

GC-Mass (theoretical value: 699.88g/mol, measured value: 699g/mol)

[ Synthesis example 9] Synthesis of R15

4.6 g (7.4 mmol) of A3, 2-chloro-4-(pyridin-4-yl)quinazoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.5g (7.4 mmol), cesium carbonate, 4.8g (14.8 mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R15 (3.8 g, 5.5 mmol, yield 74%).

GC-Mass (theoretical value: 701.85 g/mol, measured value: 701 g/mol)

[ Synthesis example 10] Synthesis of R21

4.0 g (7.4 mmol) of A4, 2-chloro-4-phenylquinazoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.4 mmol) under nitrogen flow. , cesium carbonate, 4.8g (14.8mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, R21 (3.3 g, 5.4 mmol, yield 73%).

GC-Mass (theoretical value: 614.76 g/mol, measured value: 614 g/mol)

[ Synthesis example 11] Synthesis of R24

4.0 g (7.4 mmol) of A4, 6-chloro-8-phenylquinoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.4 mmol), under nitrogen flow. Cesium carbonate, 4.8g (14.8mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R24 (3.3 g, 5.3 mmol, yield 72%).

GC-Mass (theoretical value: 613.77g/mol, measured value: 613g/mol)

[ Synthesis example 12] Synthesis of R25

4.0 g (7.4 mmol) of A4, 2-chloro-4-(pyridin-4-yl)quinazoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.5g (7.4 mmol), cesium carbonate, 4.8g (14.8mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R25 (3.3 g, 5.4 mmol, yield 73%).

GC-Mass (theoretical value: 615.74 g/mol, measured value: 615 g/mol)

[ Synthesis example 13] Synthesis of R26

4.0 g (7.4 mmol) of A4, 2-chloro-4-phenylquinazoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.4 mmol) under nitrogen flow. , cesium carbonate, 4.8g (14.8mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R27 (3.4 g, 5.5 mmol, yield 74%).

GC-Mass (theoretical value: 614.76 g/mol, measured value: 614 g/mol)

[ Synthesis example 14] Synthesis of R29

4.0 g (7.4 mmol) of A4, 6-chloro-8-phenylquinoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.4 mmol), under nitrogen flow. Cesium carbonate, 4.8g (14.8mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, R29 (3.4 g, 5.5 mmol, yield 74%).

GC-Mass (theoretical value: 613.77g/mol, measured value: 613g/mol)

[ Synthesis example 15] Synthesis of R30

4.0 g (7.4 mmol) of A4, 2-chloro-4-(pyridin-4-yl)quinazoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.5g (7.4 mmol), cesium carbonate, 4.8g (14.8mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R30 (3.4 g, 5.5 mmol, yield 74%).

GC-Mass (theoretical value: 615.74 g/mol, measured value: 615 g/mol)

[ Synthesis example 16] Synthesis of R31

4.7 g (7.6 mmol) of A6, 2-chloro-4-phenylquinazoline, 2.7 g (11.4 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.6 g (7.6 mmol) under nitrogen flow. , 5.0 g (15.2 mmol) of cesium carbonate and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, R31 (3.8 g, 5.6 mmol, yield 73%).

GC-Mass (theoretical value: 690.85 g/mol, measured value: 690 g/mol)

[ Synthesis example 17] Synthesis of R34

4.7 g (7.6 mmol) of A6, 6-chloro-8-phenylquinoline, 2.7 g (11.4 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.6 g (7.6 mmol), under nitrogen flow. Cesium carbonate, 5.0 g (15.2 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R34 (3.8 g, 5.5 mmol, yield 72%).

GC-Mass (theoretical value: 689.86 g/mol, measured value: 689 g/mol)

[ Synthesis example 18] Synthesis of R35

4.7 g (7.6 mmol) of A6, 2-chloro-4-(pyridin-4-yl)quinazoline, 2.7 g (11.4 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.6g (7.6 mmol), cesium carbonate, 5.0g (15.2 mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R35 (3.8 g, 5.6 mmol, yield 73%).

GC-Mass (theoretical value: 691.84 g/mol, measured value: 691 g/mol)

[ Synthesis example 19] Synthesis of R41

3.8 g (7.3 mmol) of A7, 2-chloro-4-phenylquinazoline, 2.6 g (11.0 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.3 mmol) under nitrogen flow. , 4.8 g (14.6 mmol) of cesium carbonate and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, R41 (3.4 g, 5.6 mmol, yield 77%).

GC-Mass (theoretical value: 598.69 g/mol, measured value: 598 g/mol)

[ Synthesis example 20] Synthesis of R44

3.8 g (7.3 mmol) of A7, 6-chloro-8-phenylquinoline, 2.6 g (11.0 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.3 mmol), under nitrogen flow. Cesium carbonate, 4.8 g (14.6 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R44 (3.4 g, 5.6 mmol, yield 77%).

GC-Mass (theoretical value: 597.70 g/mol, measured value: 597 g/mol)

[ Synthesis example 21] Synthesis of R45

3.8 g (7.3 mmol) of A7, 2-chloro-4-(pyridin-4-yl)quinazoline, 2.7 g (11.0 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.5g (7.3 mmol), cesium carbonate, 4.8g (14.6 mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, R45 (4.4 g, 5.4 mmol, yield 74%).

GC-Mass (theoretical value: 599.68 g/mol, measured value: 599 g/mol)

[ Synthesis example 22] Synthesis of R46

3.8 g (7.3 mmol) of A8, 2-chloro-4-phenylquinazoline, 2.6 g (11.0 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.3 mmol) under nitrogen flow. , 4.8 g (14.6 mmol) of cesium carbonate and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R46 (3.2 g, 5.3 mmol, yield 73%).

GC-Mass (theoretical value: 598.69 g/mol, measured value: 598 g/mol)

[ Synthesis example 23] Synthesis of R49

3.8 g (7.3 mmol) of A8, 6-chloro-8-phenylquinoline, 2.6 g (11.0 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.3 mmol), under nitrogen flow. Cesium carbonate, 4.8 g (14.6 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, R49 (3.1 g, 5.3 mmol, yield 73%).

GC-Mass (theoretical value: 597.70 g/mol, measured value: 597 g/mol)

[ Synthesis example 24] Synthesis of R50

3.8 g (7.3 mmol) of A8, 2-chloro-4-(pyridin-4-yl)quinazoline, 2.6 g (11.0 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.5g (7.3 mmol), cesium carbonate, 4.8g (14.6 mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, R50 (3.2 g, 5.3 mmol, yield 73%).

GC-Mass (theoretical value: 599.68 g/mol, measured value: 599 g/mol)

[ Synthesis example 25] Synthesis of R51

4.4 g (7.4 mmol) of A9, 6-chloro-8-phenylquinoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.4 mmol), under nitrogen flow. Cesium carbonate, 4.8 g (14.8 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R54 (3.2 g, 5.2 mmol, yield 72%).

GC-Mass (theoretical value: 623.78g/mol, measured value: 623g/mol)

[ Synthesis example 26] Synthesis of R54

4.4 g (7.4 mmol) of A9, 6-chloro-8-phenylquinoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.4 mmol), under nitrogen flow. Cesium carbonate, 4.8 g (14.8 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R54 (3.8 g, 5.6 mmol, yield 76%).

GC-Mass (theoretical value: 673.80 g/mol, measured value: 673 g/mol)

[ Synthesis example 27] Synthesis of R55

4.4 g (7.4 mmol) of A9, 2-chloro-4-(pyridin-4-yl)quinazoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.5g (7.4 mmol), cesium carbonate, 4.8g (14.8 mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R55 (3.7 g, 5.5 mmol, yield 74%).

GC-Mass (theoretical value: 675.77g/mol, measured value: 675g/mol)

[ Synthesis example 28] Synthesis of R61

4.4 g (7.4 mmol) of A10, 2-chloro-4-phenylquinazoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , and 3.5 g (7.4 mmol) of Xphos under nitrogen flow. , 4.8 g (14.8 mmol) of cesium carbonate and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, R61 (3.5 g, 5.2 mmol, yield 70%).

GC-Mass (theoretical value: 673.80 g/mol, measured value: 673 g/mol)

[ Synthesis example 29] Synthesis of R64

4.4 g (7.4 mmol) of A10, 6-chloro-8-phenylquinoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.4 mmol), under nitrogen stream. Cesium carbonate, 4.8 g (14.8 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R64 (3.5 g, 5.2 mmol, yield 70%).

GC-Mass (theoretical value: 672.81g/mol, measured value: 672g/mol)

[ Synthesis example 30] Synthesis of R65

Under a nitrogen stream, 4.4 g (7.4 mmol) of A10, 6-chloro-8-phenylquinoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.4 mmol), Cesium carbonate, 4.8 g (14.8 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R65 (3.6 g, 5.4 mmol, yield 73%).

GC-Mass (theoretical value: 674.79 g/mol, measured value: 674 g/mol)

[ Synthesis example 31] Synthesis of R66

4.4 g (7.4 mmol) of A11, 2-chloro-4-phenylquinazoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , and 3.5 g (7.4 mmol) of Xphos under nitrogen flow. , 4.8 g (14.8 mmol) of cesium carbonate and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R66 (3.5 g, 5.3 mmol, yield 71%).

GC-Mass (theoretical value: 673.80 g/mol, measured value: 673 g/mol)

[ Synthesis example 32] Synthesis of R69

Under a nitrogen stream, 4.4 g (7.4 mmol) of A11, 6-chloro-8-phenylquinoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.4 mmol), Cesium carbonate, 4.8 g (14.8 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, R69 (3.5 g, 5.3 mmol, yield 71%).

GC-Mass (theoretical value: 672.81g/mol, measured value: 672g/mol)

[ Synthesis example 33] Synthesis of R70

4.4 g (7.4 mmol) of A11, 2-chloro-4-(pyridin-4-yl)quinazoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.5g (7.4 mmol), cesium carbonate, 4.8g (14.8 mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R70 (3.7 g, 5.5 mmol, yield 74%).

GC-Mass (theoretical value: 674.79 g/mol, measured value: 674 g/mol)

[ Synthesis example 34] Synthesis of R71

5.1 g (7.6 mmol) of A12, 2-chloro-4-phenylquinazoline, 2.7 g (11.4 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , and 3.6 g (7.6 mmol) of Xphos under nitrogen flow. , 5.0 g (15.2 mmol) of cesium carbonate and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R71 (4.0 g, 5.3 mmol, yield 70%).

GC-Mass (theoretical value: 749.90 g/mol, measured value: 749 g/mol)

[ Synthesis example 35] Synthesis of R74

Under a nitrogen stream, 5.1 g (7.6 mmol) of A12, 6-chloro-8-phenylquinoline, 2.7 g (11.4 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.6 g (7.6 mmol), Cesium carbonate, 5.0 g (15.2 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R74 (4.0 g, 5.3 mmol, yield 70%).

GC-Mass (theoretical value: 748.91g/mol, measured value: 748g/mol)

[ Synthesis example 36] Synthesis of R75

5.1 g (7.6 mmol) of A12, 2-chloro-4-(pyridin-4-yl)quinazoline, 2.8 g (11.4 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.6g (7.6 mmol), cesium carbonate, 5.0g (15.2 mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, R75 (4.2 g, 5.6 mmol, yield 73%).

GC-Mass (theoretical value: 750.89 g/mol, measured value: 750 g/mol)

[ Synthesis example 37] Synthesis of R81

2.7 g (7.5 mmol) of A13, 2.7 g (11.3 mmol) of 2-chloro-4-phenylquinazoline, 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.6 g (7.5 mmol) of Xphos under nitrogen flow. , cesium carbonate, 4.9 g (15.0 mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R81 (2.3 g, 5.3 mmol, yield 71%).

GC-Mass (theoretical value: 432.51 g/mol, measured value: 432 g/mol)

[ Synthesis example 38] Synthesis of R84

2.7 g (7.5 mmol) of A13, 6-chloro-8-phenylquinoline, 2.7 g (11.3 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.6 g (7.5 mmol), under nitrogen stream. Cesium carbonate, 4.9 g (15.0 mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R84 (2.3 g, 5.3 mmol, yield 71%).

GC-Mass (theoretical value: 431.53g/mol, measured value: 431g/mol)

[ Synthesis example 39] Synthesis of R85

2.7 g (7.5 mmol) of A13, 2-chloro-4-(pyridin-4-yl)quinazoline, 2.7 g (11.3 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.6 g (7.5 mmol), cesium carbonate, 4.9 g (15.0 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R85 (2.4 g, 5.6 mmol, yield 74%).

GC-Mass (theoretical value: 433.50 g/mol, measured value: 433 g/mol)

[ Synthesis example 40] Synthesis of R86

2.7 g (7.5 mmol) of A14, 2.7 g (11.3 mmol) of 2-chloro-4-phenylquinazoline, 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.6 g (7.5 mmol) of Xphos under nitrogen flow. , 4.9 g (15.0 mmol) of cesium carbonate and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, R86 (2.3 g, 5.3 mmol, yield 70%).

GC-Mass (theoretical value: 432.51 g/mol, measured value: 432 g/mol)

[ Synthesis example 41] Synthesis of R89

2.7 g (7.5 mmol) of A14, 6-chloro-8-phenylquinoline, 2.7 g (11.3 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.6 g (7.5 mmol), under nitrogen flow. Cesium carbonate, 4.9 g (15.0 mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, R89 (2.3 g, 5.3 mmol, yield 70%).

GC-Mass (theoretical value: 431.53g/mol, measured value: 431g/mol)

[ Synthesis example 42] Synthesis of R90

2.7 g (7.5 mmol) of A14, 2-chloro-4-(pyridin-4-yl)quinazoline, 2.7 g (11.3 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.6 g (7.5 mmol), cesium carbonate, 4.9 g (15.0 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, R90 (2.4 g, 5.5 mmol, yield 73%).

GC-Mass (theoretical value: 433.50 g/mol, measured value: 433 g/mol)

[ Synthesis example 43] Synthesis of R91

3.6 g (7.0 mmol) of A16, 2.5 g (10.5 mmol) of 2-chloro-4-phenylquinazoline, 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.3 g (7.0 mmol) of Xphos under nitrogen flow. , 4.6 g (14.0 mmol) of cesium carbonate and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, R91 (2.9 g, 4.9 mmol, yield 70%).

GC-Mass (theoretical value: 584.71 g/mol, measured value: 584 g/mol)

[ Synthesis example 44] Synthesis of R94

Under nitrogen flow, 3.6 g (7.0 mmol) of A16, 6-chloro-8-phenylquinoline, 2.5 g (10.5 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.3 g (7.0 mmol), Cesium carbonate, 4.6 g (14.0 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, R94 (2.9 g, 4.9 mmol, yield 70%).

GC-Mass (theoretical value: 583.72g/mol, measured value: 583g/mol)

[ Synthesis example 45] Synthesis of R95

3.6 g (7.0 mmol) of A16, 2-chloro-4-(pyridin-4-yl)quinazoline, 2.5 g (10.5 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.3g (7.0 mmol), cesium carbonate, 4.6g (14.0 mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, R95 (3.0 g, 5.1 mmol, yield 73%).

GC-Mass (theoretical value: 585.69 g/mol, measured value: 585 g/mol)

[ Synthesis example 46] Synthesis of R96

Under nitrogen flow, 3.9 g (7.7 mmol) of A15, 2-chloro-4-phenylquinazoline, 2.8 g (11.6 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.7 g (7.7 mmol) , 5.0 g (15.4 mmol) of cesium carbonate and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R96 (3.3 g, 5.6 mmol, yield 73%).

GC-Mass (theoretical value: 584.71 g/mol, measured value: 584 g/mol)

[ Synthesis example 47] Synthesis of R99

Under a nitrogen stream, 3.9 g (7.7 mmol) of A15, 6-chloro-8-phenylquinoline, 2.8 g (11.6 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.7 g (7.7 mmol), Cesium carbonate, 5.0 g (15.4 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, R99 (3.2 g, 5.5 mmol, yield 71%).

GC-Mass (theoretical value: 583.72g/mol, measured value: 583g/mol)

[ Synthesis example 48] Synthesis of R100

3.9 g (7.7 mmol) of A15, 2-chloro-4-(pyridin-4-yl)quinazoline, 2.8 g (11.6 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.7g (7.7 mmol), cesium carbonate, 5.0g (15.4 mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R100 (3.3 g, 5.7 mmol, yield 74%).

GC-Mass (theoretical value: 585.69 g/mol, measured value: 585 g/mol)

[ Synthesis example 49] Synthesis of R101

5.0 g (7.4 mmol) of A17, 2-chloro-4-phenylquinazoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.4 mmol) under nitrogen flow. , 4.8 g (14.8 mmol) of cesium carbonate and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R101 (4.2 g, 5.6 mmol, yield 76%).

GC-Mass (theoretical value: 746.89 g/mol, measured value: 746 g/mol)

[ Synthesis example 50] Synthesis of R104

5.0 g (7.4 mmol) of A17, 6-chloro-8-phenylquinoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.4 mmol), under nitrogen flow. Cesium carbonate, 4.8 g (14.8 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R104 (4.2 g, 5.6 mmol, yield 76%).

GC-Mass (theoretical value: 746.89 g/mol, measured value: 746 g/mol)

[ Synthesis example 51] Synthesis of R105

5.0 g (7.4 mmol) of A17, 2-chloro-4-(pyridin-4-yl)quinazoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.5g (7.4 mmol), cesium carbonate, 4.8g (14.8 mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R105 (4.1 g, 5.5 mmol, yield 74%).

GC-Mass (theoretical value: 747.88g/mol, measured value: 747g/mol)

[ Synthesis example 52] Synthesis of R106

5.0 g (7.4 mmol) of A18, 2-chloro-4-phenylquinazoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.4 mmol) under nitrogen flow. , 4.8 g (14.8 mmol) of cesium carbonate and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, R106 (3.9 g, 5.2 mmol, yield 70%).

GC-Mass (theoretical value: 746.89 g/mol, measured value: 746 g/mol)

[ Synthesis example 53] Synthesis of R109

5.0 g (7.4 mmol) of A18, 6-chloro-8-phenylquinoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.4 mmol), under nitrogen stream. Cesium carbonate, 4.8 g (14.8 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, R109 (3.9 g, 5.2 mmol, yield 70%).

GC-Mass (theoretical value: 746.89 g/mol, measured value: 746 g/mol)

[ Synthesis example 54] Synthesis of R110

5.0 g (7.4 mmol) of A18, 2-chloro-4-(pyridin-4-yl)quinazoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.5g (7.4 mmol), cesium carbonate, 4.8g (14.8 mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, R110 (4.0 g, 5.4 mmol, yield 73%).

GC-Mass (theoretical value: 747.88g/mol, measured value: 747g/mol)

[ Synthesis example 55] Synthesis of R141

4.7 g (7.4 mmol) of A21, 2-chloro-4-phenylquinazoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.4 mmol) under nitrogen flow. , 4.8 g (14.8 mmol) of cesium carbonate and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, R141 (4.0 g, 5.6 mmol, yield 76%).

GC-Mass (theoretical value: 715.88g/mol, measured value: 715g/mol)

[ Synthesis example 56] Synthesis of R144

4.7 g (7.4 mmol) of A21, 6-chloro-8-phenylquinoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.4 mmol), under nitrogen flow. Cesium carbonate, 4.8 g (14.8 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R144 (4.0 g, 5.6 mmol, yield 76%).

GC-Mass (theoretical value: 714.89 g/mol, measured value: 714 g/mol)

[ Synthesis example 57] Synthesis of R161

Under nitrogen flow, 3.9 g (7.4 mmol) of A19, 2-chloro-4-phenylquinazoline, 2.6 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.4 g (7.4 mmol) , 4.7 g (14.8 mmol) of cesium carbonate and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R161 (3.1 g, 5.0 mmol, yield 70%).

GC-Mass (theoretical value: 614.69 g/mol, measured value: 614 g/mol)

[ Synthesis example 58] Synthesis of R164

Under a nitrogen stream, 3.9 g (7.4 mmol) of A19, 6-chloro-8-phenylquinoline, 2.6 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.4 g (7.4 mmol), Cesium carbonate, 4.7 g (14.8 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, R164 (3.1 g, 5.0 mmol, yield 70%).

GC-Mass (theoretical value: 613.70 g/mol, measured value: 613 g/mol)

[ Synthesis example 59] Synthesis of R181

4.2 g (7.4 mmol) of A20, 2-chloro-4-(pyridin-4-yl)quinazoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , 3.5g (7.4 mmol), cesium carbonate, 4.8g (14.8 mmol) and 90ml/30ml/30ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R181 (3.4 g, 5.2 mmol, yield 70%).

GC-Mass (theoretical value: 646.82g/mol, measured value: 646g/mol)

[ Synthesis example 60] Synthesis of R184

4.2 g (7.4 mmol) of A20, 6-chloro-8-phenylquinoline, 2.7 g (11.1 mmol), 0.1 g (5 mol%) of Pd(OAc) ₂ , Xphos, 3.5 g (7.4 mmol), under nitrogen stream. Cesium carbonate, 4.8 g (14.8 mmol) and 90 ml/30 ml/30 ml of toluene/H ₂ O/ethanol were added 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, the product was purified by column chromatography to obtain the target compound, R184 (3.4 g, 5.2 mmol, yield 70%).

GC-Mass (theoretical value: 645.83 g/mol, measured value: 645 g/mol)

[Examples 1 to 57] Fabrication of red organic electroluminescent device

The compound synthesized in the synthesis example was purified to high purity by sublimation using 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 1500 Å thin film of ITO (indium tin oxide) was washed with distilled water ultrasonic waves. After cleaning with distilled water, 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 substrate using UV for 5 minutes and using a vacuum evaporator. The substrate was transferred to .

On the ITO transparent electrode prepared in this way, m-MTDATA (60 nm)/TCTA (80 nm)/ R1, R4, R5, R6, R9, R10, R11, R14, R15, R21, R24, R25, R26, R29, R30, R31, R34, R35, R41, R44, R45, R49, R50, R51, R54, R55, R61, R64, R65, R66, R69, R70, R71, R74, R75, R81, R84, R85, R86, R89, Compound of R90, R91, R94, R95, R96, R99, R100, R101, R104, R105, R106, R109, R110, R141, R161 or R181 + 10% (piq) ₂ Ir(acac) (300nm)/BCP ( An organic electroluminescent device was manufactured by stacking in the following order: 10 nm)/Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm).

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

[ Comparative example 1] Red organic electric field Fabrication of light emitting devices

A red organic electroluminescent device was manufactured in the same process as Example 1, except that CBP was used instead of Compound R1 as the light-emitting host material when forming the light-emitting layer.

[ Evaluation example One]

The driving voltage and current efficiency were measured at a current density of 10 mA/cm2 for each organic electroluminescent device manufactured in Examples 1 to 57 and Comparative Example 1, and the results are shown in Table 1 below.

Sample host driving voltage
(V) EL peak
(nm) Current efficiency
(cd/A) Example 1 R1 3.5 621 14.8 Example 2 R4 3.5 621 15.1 Example 3 R5 3.9 621 14.8 Example 4 R6 3.8 621 15.3 Example 5 R9 3.7 621 14.2 Example 6 R10 3.4 621 16.3 Example 7 R11 3.3 621 14.2 Example 8 R14 3.3 621 15.7 Example 9 R15 3.5 621 14.1 Example 10 R21 3.6 621 15.2 Example 11 R24 3.6 621 14.1 Example 12 R25 3.8 621 16.2 Example 13 R26 3.9 621 15.8 Example 14 R29 3.9 621 15.2 Example 15 R30 3.0 621 14.9 Example 16 R31 3.2 621 15.2 Example 17 R34 3.7 621 15.2 Example 18 R35 3.3 621 15.0 Example 19 R41 3.9 621 15.1 Example 20 R44 3.6 621 14.8 Example 21 R45 3.8 621 14.8 Example 22 R46 3.5 621 15.3 Example 23 R49 3.3 621 14.7 Example 24 R50 3.5 621 14.9 Example 25 R51 3.5 621 14.5 Example 26 R54 3.6 621 15.1 Example 27 R55 3.5 621 14.8 Example 28 R61 3.9 621 15.2 Example 29 R64 3.8 621 14.6 Example 30 R65 3.5 621 15.8 Example 31 R66 3.3 621 14.9 Example 32 R69 3.5 621 15.1 Example 33 R70 3.6 621 14.2 Example 34 R71 3.6 621 15.8 Example 35 R74 3.3 621 14.8 Example 36 R75 3.9 621 16.0 Example 37 R81 3.3 621 15.1 Example 38 R84 3.6 621 15.9 Example 39 R85 3.6 621 14.9 Example 40 R86 3.5 621 15.2 Example 41 R89 3.6 621 14.8 Example 42 R90 3.9 621 15.1 Example 43 R91 3.5 621 15.3 Example 44 R94 3.9 621 15.1 Example 45 R95 3.8 621 15.0 Example 46 R96 3.8 621 15.4 Example 47 R99 3.6 621 15.1 Example 48 R100 3.5 621 14.5 Example 49 R101 3.5 621 14.7 Example 50 R104 3.9 621 15.7 Example 51 R105 3.8 621 15.0 Example 52 R106 3.7 621 15.2 Example 53 R109 3.2 621 15.8 Example 54 R110 3.3 621 15.7 Example 55 R141 3.5 621 15.9 Example 56 R161 3.1 621 15.8 Example 57 R181 3.3 621 15.5 Comparative Example 1 CBP 5.7 622 9.2

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 57), a red organic electroluminescent device using conventional CBP as a material for the light-emitting layer (Comparative Example) Compared to 1), it can be seen that it shows excellent performance in terms of efficiency and driving voltage.

[Examples 58 to 76] Preparation of blue organic electroluminescent device

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

On the ITO transparent electrode prepared as above, DS-205 (80 nm)/NPB (15 nm)/ADN + 5% DS-405 (30nm)/ R4, R9, R14, R24, R29, R34, R44, R49, An organic electroluminescent device was manufactured by stacking R54, R64, R69, R74, R84, R89, R94, R96, R99, R104 or R109 LiF (1 nm)/Al (200 nm) in that order.

The structures of NPB, ADN, and Alq ₃ used here are as follows:

[ Comparative example 2] Blue Organic electric field Manufacturing of light emitting devices

A blue organic electroluminescent device was manufactured in the same manner as in Example 58, except that the lifespan improvement layer was not included and Alq ₃ , an electron transport layer material, was deposited to 30 nm.

[ Evaluation example 2]

For the organic electroluminescent devices manufactured in Examples 58 to 76 and Comparative Example 2, the driving voltage, current efficiency, and emission wavelength were measured at a current density of 10 mA/cm2, and the results are shown in Table 2 below.

Sample electron transport layer driving voltage
(V) Current efficiency
(cd/A) Luminescence peak
(nm) Example 58 R4 3.5 8.8 458 Example 59 R9 3.4 8.9 458 Example 60 R14 3.3 9.1 458 Example 61 R24 3.3 8.2 458 Example 62 R29 3.9 7.1 459 Example 63 R34 3.5 8.9 458 Example 64 R44 3.8 9.0 458 Example 65 R49 3.0 7.6 458 Example 66 R54 3.8 8.5 458 Example 67 R64 3.3 8.3 458 Example 68 R69 3.6 9.1 458 Example 69 R74 3.3 8.5 458 Example 70 R84 3.9 7.2 459 Example 71 R89 3.3 8.3 458 Example 72 R94 3.9 9.2 458 Example 73 R96 3.1 8.8 458 Example 74 R99 3.8 9.5 458 Example 75 R104 3.0 8.1 458 Example 76 R109 3.0 7.8 458 Comparative Example 2 Alq ₃ 4.7 5.6 458

As shown in Table 2, when the compound according to the present invention was used in the electron transport layer of an organic electroluminescent device (Examples 58 to 76), when compared with the conventional organic electroluminescent device using Alq ₃ (Comparative Example 2) It can be seen that it shows excellent performance in terms of efficiency and driving voltage.

[ Example 77~83] major transport layer abandonment 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 cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, and methanol, drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then cleaning the substrate for 5 minutes using UV. Afterwards, the substrate was transferred to a vacuum laminate.

m-MTDATA (60nm)/R764, R84, R89, R94, R144, R164 or R184 (80nm)/DS-H522 + 5% DS-501 (300nm)/BCP (10nm)/ on the ITO transparent electrode prepared as above. Organic EL devices were manufactured in the following order: Alq3 (30 nm)/LiF (1 nm)/Al (200 nm).

DS-H522 and DS-501 used in device fabrication are products of Doosan Electronics BG, and the structures of m-MTDATA, TCTA, CBP, Ir(ppy) ₃ , and BCP are as follows:

[ Comparative example 3] major transport layer abandonment electric field Fabrication of light emitting devices

An organic electroluminescent device with a hole transport layer was manufactured in the same process as Example 77, except that CBP was used instead of compound R66, which was used as the hole transport layer material when forming the hole transport layer. The structure of the NPB used is as follows:

[ Evaluation example 3]

The driving voltage and current efficiency were measured at a current density of 10 mA/cm2 for each organic electroluminescent device manufactured in Examples 77 to 83 and Comparative Example 3, and the results are shown in Table 3 below.

Sample hole transport layer driving voltage
(V) Current efficiency
(cd/A) Example 77 R66 4.1 30.9 Example 78 R84 4.0 29.7 Example 79 R89 3.3 27.8 Example 80 R94 3.6 26.6 Example 81 R144 3.9 28.1 Example 82 R164 3.9 29.0 Example 83 R184 3.4 28.7 Comparative Example 3 NPB 5.3 18.1

As shown in Table 3, when the compound according to the present invention was used in the hole transport layer of an organic electroluminescent device (Examples 77 to 83), the efficiency compared to an organic electroluminescent device using a conventional NPB (Comparative Example 3) It can be seen that it shows excellent performance in terms of driving voltage.

Claims (12)

Compounds represented by Formula 4 or Formula 10:
[Formula 4]

[Formula 10]

In Formula 4 or Formula 10,
p and q are each independently 0 or 1, and P+q≤1;
R ₁ and R ₂ are phenyl groups;
L ₁ and L ₂ are each independently a single bond and a substituent represented by any one of Formulas 14 to 16 and Formula 19 below, except for cases where both L ₁ and L ₂ are single bonds,
[Formula 14]

[Formula 15]

[Formula 16]

[Formula 19]

Of Formulas 14 to 16 and Formula 19,
* refers to the part where the combination takes place;
Y ₁ is O, S, Se, N(R ₆ ), C(R ₇ )(R ₈ ) or Si(R ₉ )(R ₁₀ );
Y ₂ and Y ₃ are each independently selected from the group consisting of O, S, Se, N(R ₆ ) and C(R ₇ )(R ₈ );
Y ₄ is C or Si;
X ₂₂ to X ₃₁ are each independently N or C(R ₁₁ );
R ₃ is selected from the group consisting of an aryl group of C ₆ to C ₆₀ , a heteroaryl group of 5 to 60 nuclear atoms, an arylamine group of C ₆ to C ₆₀ , and a fluorene group, and when there are more than one R ₃ , they are are the same or different from each other;
R ₄ to R ₁₁ are each independently hydrogen, deuterium, halogen, cyano group, nitro 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, heteroaryl group with 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ ~ 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 ~ It is selected from the group consisting of a C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group, and when each of R ₄ to R ₈ and R ₁₁ is plural. They may be the same or different from each other;
The phenyl group of R ₁ and R ₂ , the aryl group, heteroaryl group, arylamine group and fluorene group of R ₃ , and the alkyl group, alkenyl group, alkynyl group, aryl group and heteroaryl group of R ₄ to R ₁₁ , aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, mono or diarylphosphinyl group, and arylsilyl group are each independently hydrogen, deuterium, Halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms Heteroaryl group, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ to C ₄₀ Alkylsilyl 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 mono or diarylphosphinyl group and C ₆ It is substituted or unsubstituted with one or more substituents selected from the group consisting of ~C ₆₀ arylsilyl groups, and when substituted with a plurality of substituents, these may be the same or different from each other. delete delete delete According to paragraph 1,
The compound wherein R ₃ is an aryl group having C ₆ to C ₆₀ or a heteroaryl group having 5 to 60 nuclear atoms. According to paragraph 1,
The R ₃ is each independently a compound selected from the group consisting of a phenyl group, a biphenyl group, a naphthalenyl group, and a substituent represented by the following formula (20):
[Formula 20]

In Formula 20,
* refers to the part where the combination takes place;
Z ₁ to Z ₅ are each independently N or C(R ₁₂ ), but at least one of Z ₁ to Z ₅ is N;
R ₁₂ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, Heteroaryl group with 5 to 60 nuclear atoms, aryloxy group with C ₆ to C ₆₀ , alkyloxy group with C ₁ to C ₄₀ , cycloalkyl group with C ₃ to C ₄₀ , heterocycloalkyl group with 3 to 40 nuclear atoms. , C ₆ ~ C ₆₀ arylamine group, C ₁ ~ C ₄₀ alkylsilyl 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 mono or diarylphosphinyl group and C ₆ ~ C ₆₀ arylsilyl group, or may be combined with an adjacent group to form a condensed ring, wherein R ₁₂ is a plurality of individuals If they are the same or different from each other;
The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group _, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, Arylphosphine group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₃ ~ C ₄₀ Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ When unsubstituted or substituted with one or more substituents selected from the group consisting of an arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group, and is substituted with a plurality of substituents, These may be the same or different from each other. According to clause 6,
A compound where the substituent represented by Formula 20 is a substituent represented by any one of the following A-1 to A-15:

In the above formulas A-1 to A-15,
n is an integer from 0 to 4, and when n is 0, it means that hydrogen is not substituted by the substituent R ₁₃ , and when n is an integer from 1 to 4, R ₁₃ is deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl 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 ₆ ~C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine group, C ₁ ~C ₄₀ alkyl 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 mono or diaryl phosphine may be selected from the group consisting of a nyl group and a C ₆ to C ₆₀ arylsilyl group, or may be combined with an adjacent group to form a condensed ring, and when there are two or more R ₁₃ , they may be the same or different from each other;
_The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, Arylphosphine group, mono or diarylphosphinyl group, and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ Arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ Unsubstituted or substituted with one or more substituents selected from the group consisting of arylboron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diarylphosphinyl group, and C ₆ ~ C ₆₀ arylsilyl group. When substituted with a plurality of substituents, they may be the same or different from each other;
* and R ₁₂ are each as defined in Formula 20 above. delete delete According to paragraph 1,
The compound represented by Formula 1 is characterized in that it is selected from the group consisting of the following compounds:















An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) 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 layers includes a compound represented by Formula 4 or Formula 10 of claim 1. According to clause 11,
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 transport layer, an electron injection layer, a lifespan improvement layer, a light-emitting layer, and a light-emitting auxiliary layer.