KR102692891B1 - 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 comprising the same. The compound according to the present invention can improve the luminous efficiency, driving voltage, lifespan, etc. of the organic electroluminescent device by being used in an organic layer, preferably a light-emitting layer, of the organic electroluminescent device.

Description

Organic compounds and organic electroluminescent devices comprising 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 comprising the same.

Starting with Bernanose's observation of organic thin film luminescence in the 1950s, research on organic electroluminescent (EL) devices continued, leading to blue electroluminescence using anthracene single crystals in 1965, and in 1987, Tang proposed an organic EL device with a laminated structure divided into functional layers, a hole layer and an emission layer. Since then, in order to create high-efficiency, long-life organic EL devices, development has been made by introducing characteristic organic layers in the device, which has led 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 layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. At this time, the material used as the organic layer can be classified into luminescent materials, hole injection materials, hole transport materials, electron transport materials, and electron injection materials according to their functions.

Luminescent materials can be classified into blue, green, and red luminescent materials according to their luminescent colors, and yellow and orange luminescent materials for better natural color realization. In addition, a host/dopant system can be used as the luminescent material to increase color purity and luminescent efficiency through energy transfer.

Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. At this time, since the development of phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescence, research is being conducted not only on phosphorescent dopants but also on phosphorescent host materials.

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

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

The present invention aims to solve the above-mentioned problems by providing a novel compound capable of improving the efficiency, lifespan, stability, etc. of an organic electroluminescent device and an organic electroluminescent device using the compound.

To achieve the above purpose, the present invention provides a compound represented by the following chemical formula 1:

[Chemical Formula 1]

In the above chemical formula 1,

At least one of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ is condensed with a ring represented by any one of the following chemical formulas 2 to 4 to form a condensed ring;

[Chemical formula 2]

[Chemical Formula 3]

[Chemical Formula 4]

In the above chemical formulas 1 to 4,

The dotted line is the part where condensation takes place;

X ₁ to X ₃ are each independently selected from the group consisting of O, S, N(Ar ₁ ), C(Ar ₂ )(Ar ₃ ), and Si(Ar ₄ )(Ar ₅ ), wherein at least one of X ₁ to X ₃ is N(Ar ₁ );

Y ₁ to Y ₆ are each independently N or C(R ₉ );

Ar ₁ Ar ₅ is each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono or Selected from the group consisting of a diarylphosphinyl group and an arylamine group having C ₆ to C ₆₀ , or capable of forming a condensed ring by combining with an adjacent group;

R ₁ to R ₈ and R ₉ , which do not form a condensed ring with the rings represented by the above chemical formulas 2 to 4, 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 having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C is selected from the group consisting of an arylboron group having a carbon number of ₆ to C ₆₀ , an arylphosphanyl group having a carbon number of ₆ to C ₆₀ , a _mono- or diarylphosphinyl group having a carbon number of 6 to C ₆₀ , and an arylamine group having a carbon number of ₆ to C ₆₀ ; and when there are multiple R ₉ , the multiple R ₉ s are the same as or different from each other;

Ar ₁ above The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, _{alkylsilyl group} , _arylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylamine group of Ar 5 and R 1 to R 9 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 ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group are unsubstituted or substituted with one or more substituents selected from the group consisting of, and when substituted with multiple substituents, they are the same as or different from each other.

In addition, the present invention provides an organic electroluminescent device including an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers includes a compound represented by the chemical formula 1 described above.

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

"Alkenyl" in the present invention is a monovalent substituent derived from an unsaturated hydrocarbon having 2 to 40 carbon atoms and a straight or branched chain having at least one carbon-carbon double bond, and examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, etc.

In the present invention, "alkynyl" is a monovalent substituent derived from an unsaturated hydrocarbon having 2 to 40 carbon atoms and a straight or branched chain having at least one carbon-carbon triple bond, examples of which include, but are not limited to, ethynyl and 2-propynyl.

The "aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. In addition, a monovalent substituent in which two or more rings are condensed with each other, contains only carbon as a ring-forming atom (for example, the number of carbon atoms may be 8 to 60), and the entire molecule has non-aromaticity may be included. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, etc.

The "heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, at least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom selected from N, O, P, S and Se. In addition, it is interpreted to include a monovalent group in which two or more rings are simply attached to each other (pendant) or condensed, and includes a heteroatom selected from N, O, P, S and Se in addition to carbon as a ring-forming atom, and the entire molecule has non-aromacity. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl; Polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl; but are not limited to, 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, etc.

"Aryloxy" in the present invention is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

"Alkyloxy" in the present invention is a monovalent substituent represented by R'O-, wherein R' means 1 to 40 alkyl, and is interpreted as including a linear, branched, or cyclic structure. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

“Arylamine” in the present invention means an amine substituted with an aryl having 6 to 60 carbon atoms.

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

"Heterocycloalkyl" in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

In the present invention, “alkylsilyl” means silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” means silyl substituted with aryl having 5 to 60 carbon atoms.

The term “fused 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.

The compound represented by the chemical formula 1 of the present invention can be used as a material for an organic layer of an organic electroluminescent device because it has excellent thermal stability and luminescence characteristics. In particular, when the compound represented by the chemical formula 1 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having excellent luminescence performance, low driving voltage, high efficiency, and long lifespan compared to conventional host materials can be manufactured, and further, a full-color display panel with improved performance and lifespan can also be manufactured.

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The novel compound of the present invention can be represented by the following chemical formula 1:

[Chemical Formula 1]

In the above chemical formula 1,

At least one of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ is condensed with a ring represented by any one of the following chemical formulae 2 to 4 to form a condensed ring, and when two or more of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₄ and R ₅ , R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ are condensed with a ring represented by the following chemical formulae 2 to 4, each of the condensed rings is the same or different;

[Chemical formula 2]

[Chemical Formula 3]

[Chemical Formula 4]

In the above chemical formulas 1 to 4,

The dotted line is the part where condensation takes place;

X ₁ to X ₃ are each independently selected from the group consisting of O, S, N(Ar ₁ ), C(Ar ₂ )(Ar ₃ ), and Si(Ar ₄ )(Ar ₅ ), wherein at least one of X ₁ to X ₃ is N(Ar ₁ );

Y ₁ to Y ₆ are each independently N or C(R ₉ );

Ar ₁ Ar ₅ is each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono or Selected from the group consisting of a diarylphosphinyl group and an arylamine group having C ₆ to C ₆₀ , or capable of forming a condensed ring by combining with an adjacent group;

R ₁ to R ₈ and R ₉ , which do not form a condensed ring with the rings represented by the above chemical formulas 2 to 4, 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 having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C is selected from the group consisting of an arylboron group having a carbon number of ₆ to C ₆₀ , an arylphosphanyl group having a carbon number of ₆ to C ₆₀ , a _mono- or diarylphosphinyl group having a carbon number of 6 to C ₆₀ , and an arylamine group having a carbon number of ₆ to C ₆₀ ; and when there are multiple R ₉ , the multiple R ₉ s are the same as or different from each other;

Ar ₁ above The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, _{alkylsilyl group} , _arylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylamine group of Ar 5 and R 1 to R 9 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 ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group are unsubstituted or substituted with one or more substituents selected from the group consisting of, and when substituted with multiple substituents, they are the same as or different from each other.

Since the compound represented by the chemical formula 1 of the present invention has a higher molecular weight than conventional materials for organic electroluminescent devices [e.g., 4,4-dicarbazolylbiphenyl (hereinafter referred to as 'CBP')], it has a high glass transition temperature and thus has excellent thermal stability, as well as excellent carrier transport ability, luminescence ability, etc. Therefore, when an organic electroluminescent device includes the compound of the chemical formula 1, the driving voltage, efficiency, lifespan, etc. of the device can be improved.

In general, in a phosphorescent emitting layer of an organic electroluminescent device, the host material must have a triplet energy gap higher than the triplet energy gap of the dopant. That is, when the lowest excited state of the host has a higher energy than the lowest emission state of the dopant, the phosphorescent emission efficiency can be improved. The compound of the above chemical formula 1 can be used as a phosphorescent host material because the energy level can be adjusted to be higher than that of the dopant by introducing a specific substituent into the basic skeleton having a high triplet energy.

In addition, the compound of the above formula 1 can control the HOMO and LUMO energy levels depending on the type of substituent introduced into the basic skeleton, and thus can have a wide band gap and high carrier transport properties. For example, when the compound is bonded to an electron withdrawing group (EWG) with high electron absorption, such as a nitrogen-containing heterocycle (e.g., a pyridine group, a pyrimidine group, a triazine group, etc.), the entire molecule has bipolar characteristics, so that the binding force between holes and electrons can be increased. In this way, the compound of the above formula 1 in which an EWG is introduced into the basic skeleton has excellent carrier transport properties and luminescence characteristics, and therefore can be used as an electron injection/transport layer material or a life-span improvement layer material in addition to an emitting layer material of an organic electroluminescent device. Meanwhile, when the compound of the above chemical formula 1 is bonded to an electron donor group (EDG) having a high electron donating property, such as an arylamine group, a carbazole group, a terphenyl group, or a triphenylene group, to the basic skeleton, injection and transport of holes occur smoothly, so it can be usefully used as a hole injection/transport layer or a light-emitting auxiliary layer material in addition to the light-emitting layer material.

As such, the compound represented by the chemical formula 1 can improve the luminescence characteristics of the organic electroluminescent device, and at the same time, improve the hole injection/transport capability, electron injection/transport capability, luminescence efficiency, driving voltage, life characteristics, etc. Therefore, the compound of the chemical formula 1 according to the present invention can be used as an organic layer material of the organic electroluminescent device, preferably an emitting layer material (green and/or red phosphorescent host material), an electron transport/injection layer material and a hole transport/injection layer material, an emitting auxiliary layer material, a life improvement layer material, and more preferably an emitting layer material, an electron injection layer material, a emitting auxiliary layer material, and a life improvement layer material.

In addition, the compound of the above chemical formula 1 can have a glass transition temperature improved by significantly increasing the molecular weight of the compound by introducing various substituents, particularly an aryl group and/or a heteroaryl group, to the basic skeleton, and thus can have higher thermal stability than conventional light-emitting materials (e.g., CBP). In addition, the compound represented by the above chemical formula 1 is also effective in suppressing crystallization of an organic layer. Therefore, an organic electroluminescent device including the compound of the chemical formula 1 according to the present invention can have significantly improved performance and lifespan characteristics, and a full-color organic light-emitting panel to which such an organic electroluminescent device is applied can also have its performance maximized.

According to a preferred embodiment of the present invention, the compound may be a compound represented by any one of the following chemical formulas A-1 to A-9:

In the above chemical formulas A-1 to A-9,

Each of X ₁ to X ₃ , R ₁ to R ₆ , R ₈ and Y ₁ to Y ₆ is as defined in the above chemical formulas 1 to 4.

According to a preferred embodiment of the present invention, R ₁ to R ₉ and Ar ₁ At least one of R 1 to Ar ₅ is a substituent represented by the following chemical formula 5, wherein R ₁ to R ₉ and Ar ₁ to Ar ₅ may be the same as or different from each other:

[Chemical Formula 5]

In the above chemical formula 5,

* indicates the part being joined;

L ₁ and L ₂ are each independently 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 ₁₀ 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 having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C ₆₀ arylborone group, C ₆ to C ₆₀ Selected from the group consisting of an arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group, or forming a condensed ring by combining with an adjacent group;

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, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group of R 10 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 ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ One or more substituents selected from the group consisting of an alkyloxy group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group are unsubstituted or substituted, and when substituted with multiple substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, the Ar ₁ And at least one of R ₉ may be a substituent represented by the chemical formula 5, in which case Ar ₁ and R ₉ may be the same or different. More preferably, Ar ₁ may be a substituent represented by the chemical formula 5.

According to a preferred embodiment of the present invention, it is preferable in terms of luminescence efficiency and driving voltage characteristics that L ₁ and L ₂ are each independently a single bond or a linker represented by any one of the following chemical formulas B-1 to B-6:

In the above chemical formulas B-1 to B-6,

* indicates the part where the combination takes place;

X ₄ and X ₅ are each independently O, S, N(Ar ₆ ), or C(Ar ₇ )(Ar ₈ );

X ₆ is N or C(Ar ₉ );

p is an integer from 0 to 4;

R ₁₁ is 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 having 3 to 40 nuclear atoms, C ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C ₆₀ arylborone group, C ₆ to C ₆₀ An arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylamine group may be selected from the group consisting of a group capable of forming a condensed ring, or may be bonded to an adjacent group, and when there are multiple R ₁₁ s, they are the same or different from each other;

Ar ₆ to Ar ₉ 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 ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ arylamine group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C ₆₀ arylborone group, C ₆ to C ₆₀ is selected from the group consisting of an arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group, or can form a condensed ring by combining with an adjacent group;

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, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group of the above R 11 and Ar 6 to Ar 9 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 ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group are unsubstituted or substituted with one or more substituents selected from the group consisting of, and when substituted with multiple substituents, they may be the same as or different from each other.

According to a preferred embodiment of the present invention, R ₁₀ may be selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C ₆ to C ₆₀ arylamine group.

According to a preferred embodiment of the present invention, R ₁₀ is hydrogen or a substituent represented by any one of the following chemical formulas C-1 to C-7, which is preferable in terms of luminous efficiency and driving voltage characteristics:

In the above chemical formulas C-1 to C-7,

* indicates the part where the combination takes place;

Z ₁ to Z ₅ are each independently N or C(R ₁₆ );

T ₁ and T ₂ are each independently selected from the group consisting of a single bond, C(R ₁₇ )(R ₁₈ ), N(R ₁₉ ), O, and S, but not both T ₁ and T ₂ are single bonds;

q and r are each independently an integer from 0 to 4;

R ₁₂ and R ₁₃ 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 ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ arylamine group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C ₆₀ arylborone group, C ₆ to C ₆₀ is selected from the group consisting of an arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group, or can form a condensed ring by combining with an adjacent group, and when there are plural of each of R ₁₂ and R ₁₃ , they are the same as or different from each other;

R ₁₄ to R ₁₉ 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 ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ arylamine group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C ₆₀ arylborone group, C ₆ to C ₆₀ is selected from the group consisting of an arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group, or can form a condensed ring by combining with an adjacent group, and when there are plural of each of R ₁₆ to R ₁₉ , they are the same or different;

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, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group of R 12 to R 19 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 ₆ to C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono- or diarylphosphinyl group, and a C ₆ to C ₆₀ arylsilyl group are unsubstituted or substituted with one or more substituents selected from the group consisting of, and when substituted with multiple substituents, they may be the same as or different from each other.

According to a preferred embodiment of the present invention, R ₁₀ may be a substituent represented by any one of the chemical formulas C-1 to C-5.

According to a preferred embodiment of the present invention, R ₁₄ and R ₁₅ may each independently be selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C ₆ to C ₆₀ arylamine group.

According to a preferred embodiment of the present invention, R ₁₄ and R ₁₅ may each be independently selected from the group consisting of a phenyl group, a biphenyl group, and a naphthalenyl group.

According to a preferred embodiment of the present invention, R ₁₀ may be a substituent represented by any one of the following chemical formulas D-1 to D-24:

In the above chemical formulas D-1 to D-24,

* indicates the part where the combination takes place;

t is an integer from 0 to 5,

u is an integer from 0 to 4;

v is an integer from 0 to 3;

w is an integer from 0 to 2;

R ₂₀ is 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 having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ alkyloxy group, C ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₆₀ arylamine group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C ₆₀ arylboron group, C ₆ to C ₆₀ arylphosphanyl group, is 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 can form a condensed ring by combining with an adjacent group, and when there are plural R ₂₀ s, 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, alkylboron group, arylboron group, arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group of the above R 20 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 ₆ to C ₆₀ aryl group, heteroaryl group having 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 ₃ ~C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylborone group, a C 6 to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono or diarylphosphinyl group and _{a C 6 to} C ₆₀ arylsilyl group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of, and when substituted with multiple substituents, they may be the same or different from each other,

Each of R ₁₂ , R ₁₃ , R ₁₆ to R ₁₉ , q and r is as defined in the above chemical formulas C-1 to C-7.

According to a preferred embodiment of the present invention, R ₁₂ , R ₁₃ and R ₂₀ may each independently be selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms and a C ₆ to C ₆₀ arylamine group.

According to a preferred embodiment of the present invention, R ₁₂ , R ₁₃ and R ₂₀ may each be independently selected from the group consisting of a phenyl group, a biphenyl group and a naphthalenyl group.

The compound represented by the chemical formula 1 of the present invention can be represented by the following compounds, but is not limited thereto:

The compound of chemical formula 1 of the present invention can be synthesized according to a general synthetic method ( see Chem. Rev. , 60 :313 (1960); J. Chem . SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995) etc.). The detailed synthetic process for the compound of the present invention will be specifically described in the synthetic examples described below.

2. Organic electroluminescent devices

Meanwhile, another aspect of the present invention provides an organic electroluminescent device comprising a compound represented by the chemical formula 1 described above.

Specifically, the present invention comprises (i) an anode, (ii) a cathode, and (iii) one or more organic layers interposed between the anode and the cathode, wherein at least one of the organic layers comprises a compound represented by the chemical formula 1. In this case, the compound represented by the chemical formula 1 may be used alone or in a mixture of two or more.

According to one example of the present invention, the organic layer of one or more layers may include at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer, and at least one of the organic layers may include a compound represented by the chemical formula 1.

Preferably, the organic layer containing the compound represented by the chemical formula 1 may be a light-emitting layer or a hole transport layer, and more preferably, when the compound represented by the chemical formula 1 is contained in the light-emitting layer, the light-emitting efficiency, brightness, power efficiency, thermal stability, and device lifespan of the organic electroluminescent device can be greatly improved.

For example, the compound represented by the chemical formula 1 may be a phosphorescent host, fluorescent host or dopant material of the emitting layer, and preferably may be a phosphorescent host of the emitting layer.

According to another example of the present invention, the organic layer of one or more layers may include at least one of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and an electron injection layer, wherein at least one organic layer may include a compound represented by the chemical formula 1.

Preferably, the organic layer containing the compound represented by the above chemical formula 1 may be a light-emitting auxiliary layer. In particular, when the compound represented by the above chemical formula 1 is contained in the light-emitting auxiliary layer material of the organic electroluminescent device, the efficiency (light-emitting efficiency and power efficiency), lifespan, and brightness of the organic electroluminescent device can be further improved, and the driving voltage can be further reduced.

According to another example of the present invention, the organic layer of one or more layers may include at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, wherein at least one organic layer may include a compound represented by the chemical formula 1.

Preferably, the organic layer containing the compound represented by the above chemical formula 1 may be an electron transport auxiliary layer. In particular, when the compound represented by the above chemical formula 1 is contained in the electron transport auxiliary layer of the organic electroluminescent device, the efficiency (luminescence efficiency and power efficiency), lifespan, and brightness of the organic electroluminescent device can be further improved, and the driving voltage can be further reduced.

The structure of the organic electroluminescent device of the present invention is not particularly limited, and for example, it may have a structure in which an anode, one or more organic layers, and a cathode are sequentially laminated on a substrate, and an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

According to an example, the organic electroluminescent device may have a structure in which an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode are sequentially laminated on a substrate, and, if necessary, a light-emitting auxiliary layer may be inserted between the hole transport layer and the light-emitting layer, and an electron injection layer may be positioned on the electron transport layer.

The organic electroluminescent device of the present invention can be manufactured by forming organic layers and electrodes using materials and methods known in the art, except that at least one of the organic layers of one or more layers, for example, the light-emitting layer or the light-emitting auxiliary layer, is formed to include a compound represented by the chemical formula 1.

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

Examples of substrates that can be used in the manufacture of the organic electroluminescent device in the present invention include, but are not limited to, silicon wafers, quartz or glass plates, metal plates, plastic films or sheets, etc.

Additionally, examples of the anode material include, but are not limited to, 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, and polyaniline; or carbon black.

Additionally, examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; multilayer materials such as LiF/Al or LiO ₂ /Al.

In addition, the materials used as the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not particularly limited, and any common material known in the art can be used without limitation.

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

[ Preparation 1] Compound Inv1 and Inv2's Synthesis

<Step 1> 2-( e-dibenzo[b,e][1,4]dioxin -2-day)-4,4,5,5- Tetramethyl -1,3,2- Dioxaborolan Synthesis

2-Bromodibenzo[b,e][1,4]dioxine (100 g, 0.38 mol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (115.8 g, 0.46 mol), Pd(dppf)Cl ₂ (31 g, 0.038 mol), and KOAc (111.9 g, 1.14 mol) were placed in a flask, 1,4-dioxane (2 L) was added to dissolve, and the mixture was heated and stirred for 8 hours. After the reaction was completed, distilled water was added, and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain compound 2-(dibenzo[b,e][1,4]dioxin-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (73 g, yield 62%).

<Step 2> 2- (2-Nitronaphthalen-1-yl)dibenzo[b,e] [1, 4] Dioxin Synthesis

In the above <Step 1>, 2-(Dibenzo[b,e][1,4]dioxin-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (73 g, 0.235 mol), 1-bromo-2-nitronaphthalene (71 g, 0.282 mol), and Pd(PPh ₃ ) ₄ (13.5 g, 0.011 mol) obtained were placed in a flask, and 2 M saturated aqueous solution of Na ₂ CO ₃ (352 mL) and 1,4-dioxane (2 L) were added to dissolve them, followed by heating and stirring for 8 hours. After the reaction was completed, distilled water was added, and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and purified by column chromatography to obtain compound 2-(2-nitronaphthalen-1-yl)dibenzo[b,e][1,4]dioxine (75 g, yield 91%).

<Step 3> Compound Inv1 , and Inv2's Synthesis

Under a nitrogen stream, 2-(2-nitronaphthalen-1-yl)dibenzo[b,e][1,4]dioxine (75 g, 0.212 mol), PPh ₃ (67 g, 0.255 mol), and 1,2-dichlorobenzene (1 L) obtained in the above <Step 2> were mixed and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, and the organic layer was extracted with dichloromethane. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain compound Inv1 (40 g, yield 58%) and compound Inv2 (12 g, yield 17%).

[ Preparation 2] Compound Inv3 and Inv4's Synthesis

The same process as in Preparation Example 1 was performed, but 2-bromo-3-nitronaphthalene was used instead of 1-bromo-2-nitronaphthalene in <Step 2> to obtain compound Inv3 (34.2 g, yield 50%) and compound Inv4 (17.1 g, yield 25%).

[ Preparation 3] Compound Inv5 and Inv6's Synthesis

The same process as in Preparation Example 1 was performed, but 2-bromo-1-nitronaphthalene was used instead of 1-bromo-2-nitronaphthalene in <Step 2> to obtain compound Inv5 (20.5 g, yield 30%) and compound Inv6 (27.4 g, yield 40%).

[ Preparation 4] Compound Inv7 and Inv8's Synthesis

<Step 1> 2-(2-Nitronaphthalen-1-yl) Cyantrene's Synthesis

2-(Dibenzo[b,e][1,4]dioxin-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (100 g, 0.384 mol), 1-bromo-2-nitronaphthalene (106 g, 0.422 mol), and Pd(PPh ₃ ) ₄ (13.3 g, 11.5 mmol) were placed in a flask, and 2 M saturated aqueous Na ₂ CO ₃ solution (576 mL) and 1,4-dioxane (2 L) were dissolved, followed by heating and stirring for 8 hours. After the reaction was completed, distilled water was added, and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and purified by column chromatography to obtain compound 2-(2-nitronaphthalen-1-yl)cyanthrene (128 g, yield 86%).

<Step 2> Compound Inv1 , and Inv2's Synthesis

Under a nitrogen stream, 2-(2-nitronaphthalen-1-yl)cyanthrene (128 g, 0.330 mol), PPh ₃ (216 g, 0.825 mol), and 1,2-dichlorobenzene (2 L) obtained in the above <Step 1> were mixed and stirred for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed, and the organic layer was extracted with dichloromethane. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain compound Inv7 (72.7 g, yield 62%) and compound Inv8 (24.5 g, yield 21%).

[ Preparation 5] Compound Inv9 and Inv10's Synthesis

The same process as in Preparation Example 4 above was performed, but 2-bromo-3-nitronaphthalene was used instead of 1-bromo-2-nitronaphthalene in <Step 1> to obtain compound Inv9 (52.6 g, yield 45%) and compound Inv12 (35.1 g, yield 30%).

[ Preparation 6] Compound Inv11 and Inv12's Synthesis

The same process as in Preparation Example 4 above was performed, but 2-bromo-1-nitronaphthalene was used instead of 1-bromo-2-nitronaphthalene in <Step 1> to obtain compound Inv11 (35.1 g, yield 30%) and compound Inv12 (46.8 g, yield 40%).

[ Reaction example 1] Cpd Synthesis of 4

In Preparation Example 1, compound Inv 2 (3.2 g, 10.0 mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (4.6 g, 12.0 mmol) synthesized were dissolved in 100 mL of toluene, and then Pd ₂ (dba) ₃ (0.9 g, 1.0 mmol) was added under nitrogen. Then, NaOtBu (2.9 g, 30 mmol) was added thereto, and (t-Bu) ₃ P (1.0 mL, 1.0 mmol) was added to the reaction solution, and the mixture was stirred under reflux for 5 hours.

After confirming the completion of the reaction by TLC, it was cooled to room temperature. After the completion of the reaction, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and purified by column chromatography to obtain compound Cpd 4 (6.2 g, yield 89%).

HRMS [M] ⁺ : 630.206

[ Reaction example 2] Cpd Synthesis of 19

In Preparation Example 1, compound Inv 2 (10 g, 30.9 mmol) and NaH (40%) (2.2 g, 37.1 mmol) were dissolved in 150 mL of toluene DMF, stirred at room temperature for 1 hour, and then 2-chloro-4-phenylquinazoline (7.8 g, 32.4 mmol) was added to the reaction solution under nitrogen, and the mixture was stirred for 12 hours.

After confirming the completion of the reaction by TLC, the produced material was filtered and washed with EtOH to obtain compound Cpd 19 (12.0 g, yield 74%).

HRMS [M] ⁺ : 527.163

[ Reaction example 3] Cpd Composite of 10

The same process as in Reaction Example 1 was performed, but 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine, thereby obtaining compound Cpd 10 (7.8 g, yield 90%).

HRMS [M] ⁺ : 706.237

[ Reaction example 4] Cpd Synthesis of 11

The same process as in Reaction Example 1 was performed, but 2-(4'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine, thereby obtaining compound Cpd 11 (6.1 g, yield 87%).

HRMS [M] ⁺ : 706.237

[ Reaction example 5] Cpd Synthesis of 24

The same process as in Reaction Example 1 was performed, but 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4-phenylquinazoline was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine, to obtain compound Cpd 24 (5.7 g, yield 84%).

HRMS [M] ⁺ : 679.226

[ Synthetic example 6] Cpd Synthesis of 28

The same process as in the above reaction example 1 was performed, but compound Inv 8 was used instead of compound Inv 2, to obtain compound Cpd 28 (5.4 g, yield 82%).

HRMS [M] ⁺ : 662.160

[ Reaction example 7] Cpd Synthesis of 34

The same process as in the above reaction example 3 was performed, but compound Inv 8 was used instead of compound Inv 2, to obtain compound Cpd 34 (6.0 g, yield 81%).

HRMS [M] ⁺ : 738.191

[ Reaction example 8] Cpd Synthesis of 35

The same process as in the above reaction example 4 was performed, but compound Inv 8 was used instead of compound Inv 2, to obtain compound Cpd 35 (6.1 g, yield 83%).

HRMS [M] ⁺ : 738.191

[ Synthetic example 9] Cpd Synthesis of 43

The same process as in the above reaction example 2 was performed, but compound Inv 8 was used instead of compound Inv 2, to obtain compound Cpd 43 (4.8 g, yield 87%).

HRMS [M] ⁺ : 559.118

[ Reaction example 10] Cpd Synthesis of 48

The same process as in the above reaction example 5 was performed, but compound Inv 8 was used instead of compound Inv 2, to obtain compound Cpd 48 (6.0 g, yield 84%).

HRMS [M] ⁺ : 711.180

[ Synthetic example 11] Cpd Synthesis of 52

The same process as in the above reaction example 1 was performed, but compound Inv 4 was used instead of compound Inv 2, to obtain compound Cpd 52 (6.2 g, yield 89%).

HRMS [M] ⁺ : 630.206

[ Reaction example 12] Cpd Synthesis of 58

The same process as in the above reaction example 3 was performed, but compound Inv 4 was used instead of compound Inv 2, to obtain compound Cpd 58 (7.8 g, yield 90%).

HRMS [M] ⁺ : 706.237

[ Reaction example 13] Cpd Synthesis of 59

The same process as in the above reaction example 4 was performed, but compound Inv 4 was used instead of compound Inv 2, to obtain compound Cpd 59 (6.1 g, yield 87%).

HRMS [M] ⁺ : 706.237

[ Synthetic example 14] Cpd Synthesis of 67

The same process as in the above reaction example 2 was performed, but compound Inv 4 was used instead of compound Inv 2, to obtain compound Cpd 67 (12.0 g, yield 74%).

HRMS [M] ⁺ : 527.163

[ Reaction example 15] Cpd Synthesis of 72

The same process as in the above reaction example 5 was performed, but compound Inv 4 was used instead of compound Inv 2, to obtain compound Cpd 72 (5.7 g, yield 84%).

HRMS [M] ⁺ : 679.226

[ Synthetic example 16] Cpd Synthesis of 76

The same process as in the above reaction example 6 was performed, but compound Inv 10 was used instead of compound Inv 8, to obtain compound Cpd 76 (5.4 g, yield 82%).

HRMS [M] ⁺ : 662.160

[ Reaction example 17] Cpd Synthesis of 82

The same process as in the above reaction example 7 was performed, but compound Inv 10 was used instead of compound Inv 8, to obtain compound Cpd 82 (6.0 g, yield 81%).

HRMS [M] ⁺ : 738.191

[ Reaction example 18] Cpd Synthesis of 83

The same process as in the above reaction example 8 was performed, but compound Inv 10 was used instead of compound Inv 8, to obtain compound Cpd 83 (6.1 g, yield 83%).

HRMS [M] ⁺ : 738.191

[ Synthetic example 19] Cpd Synthesis of 91

The same process as in the above reaction example 9 was performed, but compound Inv 10 was used instead of compound Inv 8, to obtain compound Cpd 91 (4.8 g, yield 87%).

HRMS [M] ⁺ : 559.118

[ Reaction example 20] Cpd Synthesis of 96

The same process as in the above reaction example 10 was performed, but compound Inv 10 was used instead of compound Inv 8, to obtain compound Cpd 96 (6.0 g, yield 84%).

HRMS [M] ⁺ : 711.180

[ Synthetic example 21] Cpd Composite of 100

The same process as in the above reaction example 1 was performed, but compound Inv 5 was used instead of compound Inv 2, to obtain compound Cpd 100 (6.2 g, yield 89%).

HRMS [M] ⁺ : 630.206

[ Reaction example 22] Cpd Synthesis of 106

The same process as in the above reaction example 3 was performed, but compound Inv 5 was used instead of compound Inv 2, to obtain compound Cpd 106 (7.8 g, yield 90%).

HRMS [M] ⁺ : 706.237

[ Reaction example 23] Cpd Synthesis of 107

The same process as in the above reaction example 4 was performed, but compound Inv 5 was used instead of compound Inv 2, to obtain compound Cpd 107 (6.1 g, yield 87%).

HRMS [M] ⁺ : 706.237

[ Synthetic example 24] Cpd Synthesis of 115

The same process as in the above reaction example 2 was performed, but compound Inv 5 was used instead of compound Inv 2, to obtain compound Cpd 115 (12.0 g, yield 74%).

HRMS [M] ⁺ : 527.163

[ Reaction example 25] Cpd Synthesis of 120

The same process as in the above reaction example 5 was performed, but compound Inv 5 was used instead of compound Inv 2, to obtain compound Cpd 120 (5.7 g, yield 84%).

HRMS [M] ⁺ : 679.226

[ Synthetic example 26] Cpd Synthesis of 124

The same process as in the above reaction example 6 was performed, but compound Inv 11 was used instead of compound Inv 8, to obtain compound Cpd 124 (5.4 g, yield 82%).

HRMS [M] ⁺ : 662.160

[ Reaction example 27] Cpd Synthesis of 130

The same process as in the above reaction example 7 was performed, but compound Inv 11 was used instead of compound Inv 8, to obtain compound Cpd 130 (6.0 g, yield 81%).

HRMS [M] ⁺ : 738.191

[ Reaction example 28] Cpd Synthesis of 131

The same process as in the above reaction example 8 was performed, but compound Inv 11 was used instead of compound Inv 8, to obtain compound Cpd 131 (6.1 g, yield 83%).

HRMS [M] ⁺ : 738.191

[ Synthetic example 29] Cpd Synthesis of 139

The same process as in the above reaction example 9 was performed, but compound Inv 11 was used instead of compound Inv 8, to obtain compound Cpd 139 (4.8 g, yield 87%).

HRMS [M] ⁺ : 559.118

[ Reaction example 30] Cpd Synthesis of 144

The same process as in the above reaction example 10 was performed, but compound Inv 11 was used instead of compound Inv 8, to obtain compound Cpd 144 (6.0 g, yield 84%).

HRMS [M] ⁺ : 711.180

[ Synthetic example 31] Cpd Synthesis of 148

The same process as in the above reaction example 1 was performed, but compound Inv 1 was used instead of compound Inv 2, to obtain compound Cpd 148 (6.2 g, yield 89%).

HRMS [M] ⁺ : 630.206

[ Reaction example 32] Cpd Synthesis of 154

The same process as in the above reaction example 3 was performed, but compound Inv 1 was used instead of compound Inv 2, to obtain compound Cpd 154 (7.8 g, yield 90%).

HRMS [M] ⁺ : 706.237

[ Reaction example 33] Cpd Synthesis of 155

The same process as in the above reaction example 4 was performed, but compound Inv 1 was used instead of compound Inv 2, to obtain compound Cpd 155 (6.1 g, yield 87%).

HRMS [M] ⁺ : 706.237

[ Synthetic example 34] Cpd Synthesis of 163

The same process as in the above reaction example 2 was performed, but compound Inv 1 was used instead of compound Inv 2, to obtain compound Cpd 163 (12.0 g, yield 74%).

HRMS [M] ⁺ : 527.163

[ Reaction example 35] Cpd Synthesis of 168

The same process as in the above reaction example 5 was performed, but compound Inv 1 was used instead of compound Inv 2, to obtain compound Cpd 168 (5.7 g, yield 84%).

HRMS [M] ⁺ : 679.226

[ Synthetic example 36] Cpd Synthesis of 172

The same process as in the above reaction example 6 was performed, but compound Inv 7 was used instead of compound Inv 8, to obtain compound Cpd 172 (5.4 g, yield 82%).

HRMS [M] ⁺ : 662.160

[ Reaction example 37] Cpd Synthesis of 178

The same process as in the above reaction example 7 was performed, but compound Inv 7 was used instead of compound Inv 8, to obtain compound Cpd 178 (6.0 g, yield 81%).

HRMS [M] ⁺ : 738.191

[ Reaction example 38] Cpd Synthesis of 179

The same process as in the above reaction example 8 was performed, but compound Inv 7 was used instead of compound Inv 8, to obtain compound Cpd 179 (6.1 g, yield 83%).

HRMS [M] ⁺ : 738.191

[ Synthetic example 39] Cpd Synthesis of 187

The same process as in the above reaction example 9 was performed, but compound Inv 7 was used instead of compound Inv 8, to obtain compound Cpd 187 (4.8 g, yield 87%).

HRMS [M] ⁺ : 559.118

[ Reaction example 40] Cpd Synthesis of 192

The same process as in the above reaction example 10 was performed, but compound Inv 7 was used instead of compound Inv 8, to obtain compound Cpd 192 (6.0 g, yield 84%).

HRMS [M] ⁺ : 711.180

[ Synthetic example 41] Cpd Synthesis of 196

The same process as in the above reaction example 1 was performed, but compound Inv 3 was used instead of compound Inv 2, to obtain compound Cpd 196 (6.2 g, yield 89%).

HRMS [M] ⁺ : 630.206

[ Reaction example 42] Cpd Synthesis of 202

The same process as in the above reaction example 3 was performed, but compound Inv 3 was used instead of compound Inv 2, to obtain compound Cpd 202 (7.8 g, yield 90%).

HRMS [M] ⁺ : 706.237

[ Reaction example 43] Cpd Synthesis of 203

The same process as in the above reaction example 4 was performed, but compound Inv 3 was used instead of compound Inv 2, to obtain compound Cpd 203 (6.1 g, yield 87%).

HRMS [M] ⁺ : 706.237

[ Synthetic example 44] Cpd Synthesis of 211

The same process as in the above reaction example 2 was performed, but compound Inv 3 was used instead of compound Inv 2, to obtain compound Cpd 211 (12.0 g, yield 74%).

HRMS [M] ⁺ : 527.163

[ Reaction example 45] Cpd Synthesis of 216

The same process as in the above reaction example 5 was performed, but compound Inv 3 was used instead of compound Inv 2, to obtain compound Cpd 216 (5.7 g, yield 84%).

HRMS [M] ⁺ : 679.226

[ Synthetic example 46] Cpd Synthesis of 220

The same process as in the above reaction example 6 was performed, but compound Inv 9 was used instead of compound Inv 8, to obtain compound Cpd 220 (5.4 g, yield 82%).

HRMS [M] ⁺ : 662.160

[ Reaction example 47] Cpd Synthesis of 226

The same process as in the above reaction example 7 was performed, but compound Inv 9 was used instead of compound Inv 8, to obtain compound Cpd 226 (6.0 g, yield 81%).

HRMS [M] ⁺ : 738.191

[ Reaction example 48] Cpd Synthesis of 227

The same process as in the above reaction example 8 was performed, but compound Inv 9 was used instead of compound Inv 8, to obtain compound Cpd 227 (6.1 g, yield 83%).

HRMS [M] ⁺ : 738.191

[ Synthetic example 49] Cpd Synthesis of 235

The same process as in the above reaction example 9 was performed, but compound Inv 9 was used instead of compound Inv 8, to obtain compound Cpd 235 (4.8 g, yield 87%).

HRMS [M] ⁺ : 559.118

[ Reaction example 50] Cpd Synthesis of 240

The same process as in the above reaction example 10 was performed, but compound Inv 9 was used instead of compound Inv 8, to obtain compound Cpd 240 (6.0 g, yield 84%).

HRMS [M] ⁺ : 711.180

[ Synthetic example 51] Cpd Synthesis of 244

The same process as in the above reaction example 1 was performed, but compound Inv 6 was used instead of compound Inv 2, to obtain compound Cpd 244 (6.2 g, yield 89%).

HRMS [M] ⁺ : 630.206

[ Reaction example 52] Cpd Synthesis of 250

The same process as in the above reaction example 3 was performed, but compound Inv 6 was used instead of compound Inv 2, to obtain compound Cpd 250 (7.8 g, yield 90%).

HRMS [M] ⁺ : 706.237

[ Reaction example 53] Cpd Synthesis of 251

The same process as in the above reaction example 4 was performed, but compound Inv 6 was used instead of compound Inv 2, to obtain compound Cpd 251 (6.1 g, yield 87%).

HRMS [M] ⁺ : 706.237

[ Synthetic example 54] Cpd Synthesis of 259

The same process as in the above reaction example 2 was performed, but compound Inv 6 was used instead of compound Inv 2, to obtain compound Cpd 259 (12.0 g, yield 74%).

HRMS [M] ⁺ : 527.163

[ Reaction example 55] Cpd Synthesis of 264

The same process as in the above reaction example 5 was performed, but compound Inv 6 was used instead of compound Inv 2, to obtain compound Cpd 264 (5.7 g, yield 84%).

HRMS [M] ⁺ : 679.226

[ Synthetic example 56] Cpd Synthesis of 268

The same process as in the above reaction example 6 was performed, but compound Inv 12 was used instead of compound Inv 8, to obtain compound Cpd 268 (5.4 g, yield 82%).

HRMS [M] ⁺ : 662.160

[ Reaction example 57] Cpd Synthesis of 274

The same process as in the above reaction example 7 was performed, but compound Inv 12 was used instead of compound Inv 8, to obtain compound Cpd 274 (6.0 g, yield 81%).

HRMS [M] ⁺ : 738.191

[ Reaction example 58] Cpd Synthesis of 275

The same process as in the above reaction example 8 was performed, but compound Inv 12 was used instead of compound Inv 8, to obtain compound Cpd 275 (6.1 g, yield 83%).

HRMS [M] ⁺ : 738.191

[ Synthetic example 59] Cpd Synthesis of 283

The same process as in the above reaction example 9 was performed, but compound Inv 12 was used instead of compound Inv 8, to obtain compound Cpd 283 (4.8 g, yield 87%).

HRMS [M] ⁺ : 559.118

[ Reaction example 60] Cpd Synthesis of 288

The same process as in the above reaction example 10 was performed, but compound Inv 12 was used instead of compound Inv 8, to obtain compound Cpd 288 (6.0 g, yield 84%).

HRMS [M] ⁺ : 711.180

[ Example 1 ~ 36] Green Organic Electric field Fabrication of light-emitting elements

Compound Cpd 4 synthesized in Reaction Example 1 was purified to high purity by sublimation using a commonly known method, and a green organic electroluminescent device was produced according to the following process.

First, a glass substrate coated with a 1500Å thick ITO (Indium tin oxide) film was ultrasonically washed in distilled water. After the distilled water washing, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV and transferred to a vacuum deposition machine.

On the ITO transparent electrode prepared in this manner, each compound of m-MTDATA (60 nm)/TCTA (80 nm)/Synthetic Example + 10% Ir(ppy) ₃ (30 nm)/BCP (10 nm)/Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm) was layered in that order to fabricate an organic electroluminescent device.

The structures of m-MTDATA, TCTA, Ir(ppy) ₃ , CBP, and BCP are as follows.

[ Comparative example 1] Green Organic Electric field Fabrication of light-emitting elements

A green organic electroluminescent device was manufactured using the same process as Example 1, except that CBP was used instead of the compound Cpd 4 synthesized in Reaction Example 1 as a luminescent host material when forming the luminescent layer.

[ Evaluation example 1]

For each green organic electroluminescent device manufactured in Examples 1 to 36 and Comparative Example 1, the driving voltage, current efficiency, and luminescence peak at a current density of (10) mA/cm2 were measured, and the results are shown in Table 1 below.

Sample Host Driving voltage (V) EL peak (nm) Current Efficiency (cd/A) Example 1 Cpd 4 6.82 518 39.9 Example 2 Cpd 10 6.98 517 40.2 Example 3 Cpd 11 6.89 515 38.4 Example 4 Cpd 28 6.78 518 42.4 Example 5 Cpd 34 6.69 518 42.8 Example 6 Cpd 35 6.72 517 41.7 Example 7 Cpd 52 6.70 515 42.0 Example 8 Cpd 58 6.82 518 40.3 Example 9 Cpd 59 6.84 518 41.2 Example 10 Cpd 76 7.20 525 36.4 Example 11 Cpd 82 6.82 518 39.9 Example 12 Cpd 83 6.98 517 40.2 Example 13 Cpd 100 6.89 515 38.4 Example 14 Cpd 106 6.78 518 41.4 Example 15 Cpd 107 6.69 518 42.3 Example 16 Cpd 124 6.72 517 41.7 Example 17 Cpd 130 6.70 515 41.3 Example 18 Cpd 131 6.82 518 40.6 Example 19 Cpd 148 6.84 518 41.0 Example 20 Cpd 154 6.78 518 41.1 Example 21 Cpd 155 6.69 518 42.3 Example 22 Cpd 172 6.72 517 41.2 Example 23 Cpd 178 6.70 515 41.4 Example 24 Cpd 179 6.82 518 40.1 Example 25 Cpd 196 6.84 518 39.8 Example 26 Cpd 202 6.78 515 42.4 Example 27 Cpd 203 6.81 518 41.1 Example 28 Cpd 220 6.63 518 40.5 Example 29 Cpd 226 6.78 515 42.4 Example 30 Cpd 227 6.81 518 41.1 Example 31 Cpd 244 6.79 517 40.8 Example 32 Cpd 250 6.81 518 41.1 Example 33 Cpd 251 6.79 517 40.8 Example 34 Cpd 268 6.78 515 42.4 Example 35 Cpd 274 6.81 518 41.1 Example 36 Cpd 275 6.79 517 40.8 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1 above, it was found that the green organic electroluminescent devices of Examples 1 to 36, each of which used the compound according to the present invention as a light-emitting layer material, exhibited better performance in terms of current efficiency and driving voltage than the green organic electroluminescent device of Comparative Example 1, which used conventional CBP.

[ Example 37 ~ 50] Red Organic Electric field Manufacturing of light-emitting devices

Compound Cpd 19 synthesized in Reaction Example 2 was purified by sublimation to high purity using a commonly known method, and a red organic electroluminescent device was produced according to the following process.

First, a glass substrate coated with a 1500Å thick ITO (Indium tin oxide) film was ultrasonically washed in distilled water. After the distilled water washing, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV and transferred to a vacuum deposition machine.

An organic electroluminescent device was fabricated by sequentially stacking m-MTDATA (60 nm)/TCTA (80 nm)/synthetic compound of Example + 10% (piq) ₂ Ir(acac) (30 nm)/BCP (10 nm)/Alq ₃ (30 nm)/LiF (1 nm)/Al (200 nm) on the prepared ITO transparent electrode.

[ Comparative example 2] Red organic Electric field Manufacturing of light-emitting devices

A red organic electroluminescent device was manufactured using the same process as Example 37, except that CBP was used instead of the compound Cpd 19 synthesized in Reaction Example 2 as the luminescent host material when forming the luminescent layer.

The structures of m-MTDATA, (piq) ₂ Ir(acac), CBP and BCP used in Examples 37 to 50 and Comparative Example 2 are as follows.

[ Evaluation example 2]

For each organic electroluminescent device manufactured in Examples 37 to 50 and Comparative Example 2, the driving voltage and current efficiency at a current density of 10 mA/cm2 were measured, and the results are shown in Table 2 below.

Sample Host Driving voltage (V) Current Efficiency (cd/A) Example 37 Cpd 19 4.59 12.8 Example 38 Cpd 24 4.65 12.0 Example 39 Cpd 43 4.92 10.4 Example 40 Cpd 48 4.87 9.4 Example 41 Cpd 67 4.90 9.8 Example 42 Cpd 72 4.77 11.5 Example 43 Cpd 91 4.72 10.2 Example 44 Cpd 96 4.80 11.0 Example 45 Cpd 115 4.59 12.8 Example 46 Cpd 120 4.65 12.0 Example 47 Cpd 139 4.92 10.4 Example 48 Cpd 144 4.87 9.4 Example 49 Cpd 163 4.90 9.8 Example 50 Cpd 168 4.82 11.5 Example 51 Cpd 187 4.72 10.2 Example 52 Cpd 192 4.77 10.8 Example 53 Cpd 211 4.80 10.4 Example 54 Cpd 216 4.54 12.1 Example 45 Cpd 235 4.65 12.0 Example 46 Cpd 240 4.92 10.4 Example 47 Cpd 259 4.87 9.4 Example 48 Cpd 264 4.90 9.8 Example 49 Cpd 283 4.77 11.5 Example 50 Cpd 288 4.87 9.4 Comparative Example 2 CBP 5.25 8.2

As shown in Table 2 above, 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 37 to 50), it was found that it exhibited superior performance in terms of efficiency and driving voltage compared to a red organic electroluminescent device (Comparative Example 2) in which CBP was used as a material for the light-emitting layer of the conventional device.

Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and it is possible to implement various modifications within the scope of the claims and the detailed description of the invention, which also naturally fall within the scope of the invention.

Claims (12)

A compound represented by the following chemical formula 1:
[Chemical Formula 1]

In the above chemical formula 1,
One of R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ is condensed with a ring represented by any one of the following chemical formulas 2 to 4 to form a condensed ring;
[Chemical formula 2]

[Chemical Formula 3]

[Chemical Formula 4]

In the above chemical formulas 1 to 4,
The dotted line is the part where condensation takes place;
R ₁ to R ₈ , which do not form a condensed ring with the rings represented by the above chemical formulas 2 to 4, are hydrogen;
Y ₁ to Y ₆ are CH;
X ₁ and X ₂ are each independently O, and X ₃ is N(Ar ₁ );
Ar ₁ is a substituent represented by the following chemical formula 5;
[Chemical Formula 5]

In the above chemical formula 5,
* indicates the part being joined;
A compound in which L ₁ and L ₂ are each independently a single bond or a linker represented by any one of the following chemical formulae B-1, B-2 and B-6:

In the above chemical formulas B-1, B-2 and B-6,
* indicates the part where the combination takes place;
X ₆ is N;
p is 0;
R ₁₁ is absent;
R ₁₀ is a dibenzothiophene group;
The dibenzothiophene group of the above R ₁₀ is 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 ₆ to C ₆₀ aryl group, heteroaryl group having 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 ₃ to C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C ₆₀ arylborone group, C ₆ to C It is unsubstituted or substituted with one or more substituents selected from the group consisting of an arylphosphanyl group of ₆₀ , a mono- or diarylphosphinyl group of C ₆ to C ₆₀ , and an arylsilyl group of C ₆ to C ₆₀ , and when substituted with multiple substituents, they are the same as or different from each other.
delete delete delete delete delete delete delete delete In the first paragraph,
The compound is characterized in that the compound is selected from the group consisting of the following compounds:





An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode,
An organic electroluminescent device characterized in that at least one of the organic layers of one or more layers comprises a compound represented by the chemical formula 1 of claim 1. In Article 11,
An organic electroluminescent device, wherein the organic layer containing the compound is selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron transport auxiliary layer, an electron injection layer, a life-span improvement layer, a light-emitting layer, and a light-emitting auxiliary layer.