WO2017111543A1 - Organic compound and organic electroluminescent device comprising same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device comprising same, the compound, according to the present invention, being used on an organic layer, preferably a light-emitting layer, of an organic electroluminescent device, thereby enabling the improvement of the light-emitting efficiency, driving voltage and lifespan of the organic electroluminescent device.

Description

Organic compound and organic electroluminescent device comprising the same

The present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.

Investigating organic electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965, based on observation of Bernanose's organic thin-film emission, followed by Tang in 1987. ), An organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer is proposed. Since then, in order to make a high efficiency, high-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.

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

The light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors. In addition, a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.

The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times compared to the fluorescence, studies on phosphorescent host materials as well as phosphorescent dopants have been conducted.

Hole injection layer, hole transport layer to date. NPB, BCP, Alq ₃ and the like are widely known as the hole blocking layer and the electron transporting layer material, and anthracene derivatives have been reported as the light emitting layer material. Particularly, 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 the light emitting layer materials, are blue, green, and red. (red) is used as the phosphorescent dopant material, 4,4-dicarbazolybiphenyl (CBP) is used as the phosphorescent host material.

However, the conventional organic material has an advantageous aspect in terms of light emission characteristics, but the thermal stability is not very good due to the low glass transition temperature, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, development of the organic material layer material which is excellent in performance is calculated | required.

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

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

[Formula 1]

In Chemical Formula 1,

L ₁ to L ₄ are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;

Ar ₁ is a C ₆ -C ₆₀ aryl group or a heteroaryl group of 5 to 60 nuclear atoms;

The arylene group and heteroarylene group of L ₁ to L _4, the aryl group and heteroaryl group of Ar ₁ 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, 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ Alkyl Oxy group, C ₆ to C ₆₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl Boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group When substituted or unsubstituted with one or more substituents selected, and substituted with a plurality of substituents, they may be the same or different from each other;

Ar ₂ and Ar ₃ are each independently hydrogen or a substituent selected from the group represented by Formulas A-1 to A-24, but Ar ₂ and Ar ₃ are different from each other;

In Chemical Formulas A-1 to A-24,

* Means the part where the bond is made;

Z ₁ to Z ₅ are each independently N or C (R ₇ );

Y ₁ and Y ₂ are each independently selected from the group consisting of a single bond, C (R ₈ ) (R ₉ ), N (R ₁₀ ), O and S, but both Y ₁ and Y ₂ are not single bonds;

m and n are each independently an integer from 0 to 4;

l is an integer from 0 to 3;

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 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ 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 An arylphosphanyl group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group, and a C ₆ ~ C ₆₀ arylamine group may be selected from the group consisting of or adjacent to a condensed ring, R ₁ And when there are a plurality of R _{2 s} , they are the same or different from each other;

R ₃ to R ₁₀ 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 ₃ ~ C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C _5-60 heteroaryl group, C ₁ -C ₄₀ alkyloxy group, C _6- 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 ~ mono or diaryl phosphine of C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine or adjacent groups bond to which they are attached may form a fused ring, wherein When each of R ₇ to R ₁₀ plural is 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 of the above R ₁ to R ₁₀ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ selected from the group consisting of C ₆₀ aryl silyl When substituted by one or more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.

The present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers provides an organic electroluminescent device comprising the compound of Formula 1. .

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

"Alkenyl" in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon double bond, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.

"Alkynyl" in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon triple bond, examples of which are ethynyl. , 2-propynyl, and the like, but is not limited thereto.

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, monovalent having two or more rings condensed with each other, containing only carbon as a ring forming atom (for example, may have 8 to 60 carbon atoms), and the whole molecule has non-aromacity Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. 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, two or more rings are simply pendant or condensed with each other, and in addition to carbon as a ring forming atom, a hetero atom selected from N, O, P, S and Se, the entire molecule is non-aromatic (non- It is also interpreted to include monovalent groups having aromacity). Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" 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, diphenyloxy, and the like.

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

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

By "cycloalkyl" in the present invention is meant monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

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

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.

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

Since the compound of the present invention has excellent thermal stability, carrier transporting ability, light emitting ability, and the like, it can be usefully applied as an organic material layer material of an organic EL device.

In addition, the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel since the aspect of light emission performance, driving voltage, lifespan, efficiency, etc. is greatly improved.

The present invention provides a compound represented by Formula 1:

[Formula 1]

In Chemical Formula 1,

L ₁ to L ₄ are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;

Ar ₁ is a C ₆ -C ₆₀ aryl group or a heteroaryl group of 5 to 60 nuclear atoms;

The arylene group and heteroarylene group of L ₁ to L _4, the aryl group and heteroaryl group of Ar ₁ 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, 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ Alkyl Oxy group, C ₆ to C ₆₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl Boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group When substituted or unsubstituted with one or more substituents selected, and substituted with a plurality of substituents, they may be the same or different from each other;

Ar ₂ and Ar ₃ are each independently hydrogen or a substituent selected from the group represented by Formulas A-1 to A-24, but Ar ₂ and Ar ₃ are different from each other;

In Chemical Formulas A-1 to A-24,

* Means the part where the bond is made;

Z ₁ to Z ₅ are each independently N or C (R ₇ );

Y ₁ and Y ₂ are each independently selected from the group consisting of a single bond, C (R ₈ ) (R ₉ ), N (R ₁₀ ), O and S, but both Y ₁ and Y ₂ are not single bonds;

m and n are each independently an integer from 0 to 4;

l is an integer from 0 to 3;

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 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ 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 An arylphosphanyl group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group, and a C ₆ ~ C ₆₀ arylamine group may be selected from the group consisting of or adjacent to a condensed ring, R ₁ And when there are a plurality of R _{2 s} , they are the same or different from each other;

R ₃ to R ₁₀ 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 ₃ ~ C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C _5-60 heteroaryl group, C ₁ -C ₄₀ alkyloxy group, C _6- 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 ~ mono or diaryl phosphine of C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine or adjacent groups bond to which they are attached may form a fused ring, wherein When each of R ₇ to R ₁₀ plural is 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 of the above R ₁ to R ₁₀ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ selected from the group consisting of C ₆₀ aryl silyl When substituted by one or more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.

Hereinafter, the present invention will be described in detail.

1. New Organic Compounds

The novel compounds of the present invention can be represented by the following formula (1):

[Formula 1]

In Chemical Formula 1,

L ₁ to L ₄ are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;

Ar ₁ is C ₆ ~ C ₆₀ aryl group or a nuclear atoms of 5 to 60 heteroaryl group;

The arylene group and heteroarylene group of L ₁ to L _4, the aryl group and heteroaryl group of Ar ₁ 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, 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ Alkyl Oxy group, C ₆ to C ₆₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl Boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group When substituted or unsubstituted with one or more substituents selected, and substituted with a plurality of substituents, they may be the same or different from each other;

Ar ₂ and Ar ₃ are each independently hydrogen or a substituent selected from the group represented by Formulas A-1 to A-24, but Ar ₂ and Ar ₃ are different from each other;

In Chemical Formulas A-1 to A-24,

* Means the part where the bond is made;

Z ₁ to Z ₅ are each independently N or C (R ₇ );

Y ₁ and Y ₂ are each independently selected from the group consisting of a single bond, C (R ₈ ) (R ₉ ), N (R ₁₀ ), O and S, but both Y ₁ and Y ₂ are not single bonds;

m and n are each independently an integer from 0 to 4;

l is an integer from 0 to 3;

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 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ 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 An arylphosphanyl group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group, and a C ₆ ~ C ₆₀ arylamine group may be selected from the group consisting of or adjacent to a condensed ring, R ₁ And when there are a plurality of R _{2 s} , they are the same or different from each other;

R ₃ to R ₁₀ 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 ₃ ~ C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C _5-60 heteroaryl group, C ₁ -C ₄₀ alkyloxy group, C _6- 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 ~ mono or diaryl phosphine of C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine or adjacent groups bond to which they are attached may form a fused ring, wherein When each of R ₇ to R ₁₀ plural is 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 of the above R ₁ to R ₁₀ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ selected from the group consisting of C ₆₀ aryl silyl When substituted by one or more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.

According to one preferred embodiment of the present invention, the compound may be a compound represented by the following formula (2):

[Formula 2]

In Chemical Formula 2,

L ₁ to L ₄ and Ar ₁ to Ar ₃ are each as defined in Chemical Formula 1.

The novel compound according to the present invention is a structure that combines various asymmetric substituents at positions 3 and 6 of the carbazole moiety, and has a larger energy bandgap than a conventional organic electroluminescent device material (eg, CBP), and a wide energy band gap. While having, it is possible to increase the binding force between the hole and the electron. Therefore, when the compound of Formula 1 is used in an organic electroluminescent device, the driving voltage, efficiency (luminescence efficiency, power efficiency), lifetime, and luminance of the device may be improved.

In addition, the compounds of the present invention described above are relatively easy to control properties due to the asymmetric substituents bonded to the basic skeleton. For example, the triphenylene group has a relatively small difference in (singlet energy-triplet energy) when compared to biphenyls having similar triplet energy, and triphenylene group and benzo- When compared to fused thiophenyl groups, both are used as EDG, but triphenylene groups have better electron transport than hole transport, but in the case of benzo-fused thiophenyl groups, their properties are reversed. It is easy to improve.

Therefore, when the compound of the present invention is applied to an organic electroluminescent device, since it can exhibit excellent characteristics as a host material of the light emitting layer compared to the conventional CBP, the phosphorescence properties of the device is improved, and the hole injection ability and / or transport ability, Luminous efficiency, driving voltage, lifespan characteristics and the like can be improved. And the energy level can be adjusted according to the substituents to have a wide bandgap (sky blue ~ red), and thus can be applied not only to the light emitting layer, but also to the electron transport auxiliary layer, electron transport layer, hole transport layer, hole injection layer, etc. Can be.

In addition, by significantly increasing the molecular weight of the compound of the present invention, the glass transition temperature can be improved, thereby having a higher thermal stability than conventional CBP. In addition, the thermal stability of the compound may not only be improved, but also effective in suppressing crystallization of the organic layer including the compound of Formula 1. Therefore, the device including the compound of formula 1 according to the present invention can greatly improve the durability and life characteristics.

In addition, when the compound of Formula 1 according to the present invention is adopted as a hole injection / transport layer material, an electron injection / transport layer material, a blue, green and / or red phosphorescent host material of an organic electroluminescent device, efficiency and lifespan compared to conventional CBP In terms of excellent effects can be achieved. Therefore, the compound according to the present invention can greatly contribute to improving the performance and lifespan of the organic EL device, and in particular, the device life improvement has a great effect in maximizing the performance in the full color organic light emitting panel.

According to one preferred embodiment of the present invention, Ar ₂ and Ar ₃ are each independently hydrogen or a substituent selected from the group consisting of Formulas A-5 and A-10 to A-24, but Ar ₂ and Ar ₃ Are characterized in that they are different from each other.

Further, according to one preferred embodiment of the present invention, when any one of Ar ₂ and Ar ₃ is hydrogen, the rest is a substituent selected from the group represented by the formula A-5 and A-10 to A-24 Can be.

According to one preferred embodiment of the present invention, L ₁ to L ₄ are each independently selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a naphthalenyl group, a fluorenyl group and a carbazolyl group, more preferably May be selected from the group consisting of a single bond, a phenylene group, a biphenylene group and a naphthalenyl group.

According to a preferred embodiment of the present invention, R ₁ to R ₃ are each independently selected from the group consisting of C ₁ ~ C ₁₀ Alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group of nuclear atoms Can be selected.

According to one preferred embodiment of the present invention, R ₁ to R ₃ are each independently selected from the group consisting of methyl group, ethyl group, propanyl group, butyl group, phenyl group, biphenyl group and naphthalenyl group,

The methyl group, ethyl group, propanyl group, butyl group, phenyl group, biphenyl group, and naphthalenyl group of R ₁ to R ₃ are each independently deuterium, halogen, C ₁ -C ₁₀ alkyl group and C ₆ -C ₆₀ aryl group If unsubstituted or substituted with one or more substituents selected from the group consisting of, they may be the same or different from each other.

According to one preferred embodiment of the present invention, R ₁ to R ₃ are each independently selected from the group consisting of methyl group, ethyl group, propanyl group, butyl group, phenyl group, biphenyl group and naphthalenyl group,

The methyl group, ethyl group, propanyl group, butyl group, phenyl group, biphenyl group and naphthalenyl group of R ₁ to R ₃ are each independently substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen and phenyl group. , When 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, R ₄ to R ₆ are each independently hydrogen, C ₁ ~ C ₄₀ Alkyl group, C ₆ ~ C ₆₀ An aryl group and a nuclear atom of 5 to 60 heteroaryl group Can be selected from the group.

According to a preferred embodiment of the present invention, R ₄ to R ₆ may be independently selected from the group consisting of hydrogen, phenyl group, biphenyl group, fluorenyl group and naphthalenyl group.

According to one preferred embodiment of the present invention, Ar ₁ is preferably a substituent selected from the group represented by the following formulas B-1 to B-9 in terms of luminous efficiency, but is not limited thereto:

In Chemical Formulas B-1 to B-9,

* Means the part where the bond is made;

X ₁ to X ₈ are each independently N or C (R ₁₆ );

Any one of X ₁ to X ₄ connected to L ₂ in Formula B-2 is C (R ₁₆ ), wherein R ₁₆ is absent;

T ₁ is O, S, N (R ₁₇ ), C (R ₁₈ ) (R ₁₉ ) or SO ₂ ;

R ₁₁ , R ₁₄ to R ₁₉ 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 ₃ -C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ 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, 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 arylamine group, or a group selected from or adjacent to (eg, a plurality of adjacent R) ₁₆ may bind to each other, etc.) to form a condensed ring, and when there are a plurality of R _{16 s} , they are the same or different from each other;

q and r are each independently integers of 0 to 4;

p is an integer from 0 to 3;

R ₁₂ and R ₁₃ 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 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ 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 An arylphosphanyl group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylamine group, or a group selected from or adjacent to each other (for example, adjacent other R ₁₂ or R _13, etc.) May form a condensed ring, and each of R ₁₂ and R ₁₃ is 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 of the above R ₁₁ to R ₁₉ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, halogen C ₁ -C ₄₀ alkyl, C ₂ ~ C ₄₀ alkenyl group, an aryloxy group of C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ of the C ₆₀ aryl phosphazene group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ aryl of C ₆₀ silyl When substituted by one or more substituent species selected from the group consisting of or being substituted by plural substituents Beach and ring, they may be the same or different from each other.

According to one preferred embodiment of the present invention, Ar ₁ may be a substituent selected from the group consisting of Formulas B-2 to B-5 and B-9.

According to one preferred embodiment of the present invention, R ₁₁ to R ₁₆ may be each independently selected from the group consisting of C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group of nuclear atoms.

According to one preferred embodiment of the present invention, R ₁₁ to R ₁₆ are each independently selected from the group consisting of a phenyl group, a biphenyl group, a pyridinyl group and a naphthalenyl group,

The phenyl group, biphenyl group, pyridinyl group and naphthalenyl group of R ₁₁ to R ₁₆ are each independently halogen, cyano group, alkyl group of C ₁ to C ₁₀ , alkyl group of halogen C ₁ to C ₄ and C ₆ to C ₆₀ If unsubstituted or substituted with one or more substituents selected from the group consisting of aryl groups, they may be the same or different from each other.

According to one preferred embodiment of the present invention, R ₁₁ to R ₁₆ are each independently selected from the group consisting of a phenyl group, a biphenyl group, a pyridinyl group and a naphthalenyl group,

The phenyl group, biphenyl group, pyridinyl group and naphthalenyl group of R ₁₁ to R ₁₆ are each independently composed of a cyano group, a fluorine group, a methyl group, an ethyl group, a butyl group, a cyano group, a trifluoroethanyl group and a naphthalenyl group When substituted or unsubstituted with one or more substituents selected from the group, and substituted with a plurality of substituents, they may be the same or different from each other.

According to one preferred embodiment of the present invention, Ar ₁ may be a substituent selected from the group represented by Formula F-1 to F-26, but is not limited thereto:

In Chemical Formulas F-1 to F-26,

* Means the part where the bond is made;

t and x are each independently an integer from 0 to 5;

u, q and r are each independently integers of 0 to 4;

v is an integer from 0 to 3;

w is an integer from 0 to 2;

R ₁₂ , R ₁₃ , R ₂₀ and R ₂₁ 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, 5 to 60 heteroaryl group of nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkyl boron groups, C ₆ to C ₆₀ aryl boron groups , C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group selected from the group consisting of, or in combination with an adjacent group condensed ring Can be formed, and when R ₁₂ , R ₁₃ , R ₂₀ and R ₂₁ are each plural, they are the same as or different from each other;

R _11, R ₁₆ to R ₁₉ 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, nuclear atom 5 ~ 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₃ ~ C ₄₀ cycloalkyl group, nucleus Heterocycloalkyl group having 3 to 40 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 arylphosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ An arylsilyl group or selected from the group consisting of a condensed ring to combine with Can be;

The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group and alkylsilyl group of R ₁₁ to R ₁₃ and R ₁₆ to R ₂₁ , Alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl 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 to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ Alkoxyoxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ boron alkyl group, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group in the silyl made If true, and substituted or unsubstituted by one or more substituent species selected from the group, which is substituted with plural substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, Ar ₁ is preferably a substituent selected from the group consisting of the formula F-1 to F-15, F-21, F-22 and F-26 in terms of luminous efficiency. .

Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:

In the present invention, the compound represented by Chemical Formula 1 may be synthesized according to a general synthetic method (Chem. Rev., 60: 313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) et al. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.

2. Organic Electric field  Light emitting element

On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the formula (1) according to the present invention.

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer It includes a compound represented by the formula (1). In this case, the compound may be used alone or mixed two or more.

The at least one organic material layer may be at least one of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, a life improvement layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer, wherein at least one organic compound layer The compound represented by 1 may be included, and preferably a light emitting layer may be included.

According to the exemplary embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, and may include a compound represented by Chemical Formula 1 as the host material. As such, when the compound represented by Chemical Formula 1 is included as a light emitting layer material of the organic electroluminescent device, preferably a green phosphorescent host, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency and power efficiency), lifespan, brightness and driving voltage can be improved.

The structure of the organic EL 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. In this case, an electron transport auxiliary layer may be further stacked between the emission layer and the electron transport layer, and an electron injection layer may be further stacked on the electron transport layer. In the present invention, at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, the electron transport auxiliary layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer or the electron transport layer is It may include a compound represented by the formula (1).

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

The organic EL device of the present invention is a material and method known in the art, except that at least one or more of the organic material layer (for example, the light emitting layer or the electron transport layer) is formed to include the compound represented by the formula (1) It can be prepared by forming other organic material layer and electrode using.

The organic material layer may 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.

The substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.

In addition, examples of the anode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), 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.

The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like.

Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the invention, the present invention is not limited by the following examples.

[ Preparation  1] Synthesis of A-1

<Step 1> Synthesis of A-1

3-bromo-6-phenyl-9H-carbazole (3.22 g, 10 mmol), [1,1'-biphenyl] -3-ylboronic acid (1.98 g, 10 mmol), K ₂ CO under a nitrogen stream ₃ (2.76 g, 20 mmol), Pd (PPh ₃ ) 4 (0.58 g, 0.5 mmol), THF (60 mL), and purified water (15 mL) were mixed and stirred at 110 ° C. for 12 hours. After cooling to room temperature, H2O was added and extracted using brine. After removing moisture with Na ₂ SO 4, the organic layer was concentrated and subjected to column chromatography to obtain A-1 (2.77 g, 70%) as a target compound.

¹ H-NMR: δ 7.45 (m, 6H), 7.61 (d, 2H), 7.75 (m, 7H), 7.90 (m, 5H), 11.66 (s, 1H)

[ Preparation  2] Synthesis of A-2

<Step 1> Synthesis of A-2

[1,1'-biphenyl] -4-ylboronic acid (1.98 g, 10 mmol) was used instead of the [1,1'-biphenyl] -3-ylboronic acid used in <Step 1> of Preparation Example 1. Except for using the same procedure as in <Step 1> of Preparation Example 1 to obtain A-2.

¹ H-NMR: δ 7.25 (m, 4H), 7.45 (m, 6H), 7.76 (m, 6H), 7.89 (m, 2H), 7.99 (m, 2H), 11.66 (s, 1H)

[ Preparation  3] Synthesis of A-3

<Step 1> Synthesis of A-3

3-([1,1'-biphenyl] -3-yl) -6-bromo-9H- instead of 3-bromo-6-phenyl-9H-carbazole used in <step 1> of Preparation Example 1 Carbazole (3.98 g, 10 mmol) and dibenzo [b, d] furan-4-ylboronic acid (2.12 g, 10 mmol) instead of [1,1'-biphenyl] -3-ylboronic acid Except for using the same procedure as in <Step 1> of Preparation Example 1 to obtain A-3.

¹ H-NMR: δ 7.50 (m, 9H), 7.70 (m, 5H), 8.00 (m, 8H), 11.64 (s, 1H)

[ Preparation  4] Synthesis of A-4

<Step 1> Synthesis of A-4

3 3-([1,1'-biphenyl] -4-yl) -6-bromo-9H instead of 3-bromo-6-phenyl-9H-carbazole used in <step 1> of Preparation Example 1 -Carbazole (3.98 g, 10 mmol) with dibenzo [b, d] thiophen-2-ylboronic acid (2.28 g, 10 mmol) instead of [1,1'-biphenyl] -3-ylboronic acid A-4 was obtained in the same manner as in <Step 1> of Preparation Example 1, except for using).

¹ H-NMR: δ 7.25 (m, 4H), 7.49 (m, 5H), 7.75 (m, 4H), 7.99 (m, 6H), 8.12 (m, 2H), 8.45 (d, 1H), 11.65 ( s, 1 H)

[ Preparation  5] Synthesis of A-5

<Step 1> 3- Chloro -6- ( Triphenylene 2-yl) -9H- Carbazole  synthesis

Instead of 3-bromo-6-phenyl-9H-carbazole used in <Step 1> of Preparation Example 1, 3-bromo-6-chloro-9H-carbazole (2.80 g, 10 mmol) was used, and [1 The same procedure as in <Step 1> of Preparation Example 1 was performed except that triphenylene-2-ylboronic acid (2.72 g, 10 mmol) was used instead of, 1'-biphenyl] -3-ylboronic acid. This gave 3-chloro-6- (triphenylen-2-yl) -9H-carbazole.

* ¹ H-NMR: δ 7.09 (d, 1H), 7.60 (m, 9H), 7.89 (s, 1H), 7.99 (d, 1H), 8.35 (m, 3H), 9.26 (s, 1H), 9.60 (d, 1 H), 11.63 (s, 1 H)

<Step 2> Synthesis of A-5

3-chloro-6- (triphenylen-2-yl) -9H-carbazole (4.27 g, 10.0 mmol), (9,9-dimethyl-9H-fluoren-2-yl) boronic acid under nitrogen stream 2.38 g, 10.0 mmol), Cs ₂ CO ₃ (6.51 g, 20.0 mmol), Pd (OAc) ₂ (0.11 g, 5 mol%) and X-Phos (0.47 g, 1.00 mmol) were added to 120 ml / 40 ml of THF / H ₂ O and stirred at 90 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using a column chromatography to obtain the target compound A-5 (3.51 g, yield 60%).

¹ H-NMR: δ 1.69 (s, 6H), 7.33 (m, 2H), 7.70 (m, 10H), 7.89 (m, 4H), 7.99 (m, 2H), 8.09 (d, 1H), 8.33 ( m, 3H), 9.26 (s, 1H), 9.60 (d, 1H), 11.63 (s, 1H)

[ Preparation  6] Synthesis of A-6

<Step 1> 3- Chloro -6- (3- (phenanthren-9-yl) phenyl) -9H- Carbazole  synthesis

Except for using (3- (phenanthrene-9-yl) phenyl) boronic acid (2.98 g, 10 mmol) instead of the triphenylene-2-ylboronic acid used in <Step 1> of Preparation Example 5 3-Chloro-6- (3- (phenanthren-9-yl) phenyl) -9H-carbazole was obtained in the same manner as in <Step 1> of Preparation Example 5.

¹ H-NMR: δ 7.09 (d, 1H), 7.66 (m, 10H), 7.95 (m, 5H), 8.27 (d, 1H), 8.84 (d, 1H), 9.08 (d, 1H), 11.68 ( s, 1 H)

<Step 2> Synthesis of A-6

Instead of 3-chloro-6- (triphenylen-2-yl) -9H-carbazole used in <step 2> of Preparation Example 5, 3-chloro-6- ( Naphthalene-2- instead of (9,9-dimethyl-9H-fluoren-2-yl) boronic acid using 3- (phenanthren-9-yl) phenyl) -9H-carbazole (4.53 g, 10 mmol) A-6 was obtained by the same procedure as <Step 2> of Preparation Example 5 except for using ilboronic acid (1.71 g, 10.0 mmol).

¹ H-NMR: δ 7.38 (d, 1H), 7.66 (m, 12H), 7.94 (m, 10H), 8.27 (d, 1H), 8.84 (d, 1H), 9.08 (d, 1H), 11.68 ( s, 1 H)

[ Preparation  7] Synthesis of A-7

<Step 1> 3-([1,1 ': 3', 1 ''- Terphenyl ] -5'-day) -6- Chloro -9H- Carbazole  synthesis

[1,1 ': 3', 1 ''-terphenyl] -5'-ylboronic acid (2.74 g, 10 mmol) instead of the triphenylene-2-ylboronic acid used in <Step 1> of Preparation Example 5 Except for using), the same process as in <Step 1> of Preparation Example 5 was carried out to 3-([1,1 ': 3', 1 ''-terphenyl] -5'-yl) -6 -Chloro-9H-carbazole was obtained.

¹ H-NMR: δ 7.09 (d, 1H), 7.52 (m, 8H), 7.76 (m, 5H), 7.89 (s, 1H), 8.00 (m, 4H), 11.66 (s, 1H)

<Step 2> Synthesis of A-7

3-([1,1] obtained in <Step 1> of Preparation Example 7 in place of 3-chloro-6- (triphenylen-2-yl) -9H-carbazole used in <Step 2> of Preparation Example 5 ': 3', 1 ''-terphenyl] -5'-yl) -6-chloro-9H-carbazole (4.29 g, 10 mmol) and (9,9-dimethyl-9H-fluorene-2 The same procedure as in <Step 2> of Preparation Example 5 was carried out except that 9,9'-spirobi [fluorene] -4-ylboronic acid (3.60 g, 10.0 mmol) was used instead of -yl) boronic acid. This gave A-7.

¹ H-NMR: δ 7.47 (m, 16H), 7.65 (d, 1H), 7.77 (m, 7H), 7.89 (m, 10H), 11.66 (s, 1H)

[ Preparation  8] Synthesis of A-8

<Step 1> 3- Chloro -6- ( Fluoranthene -3-yl) -9H- Carbazole  synthesis

Except for using fluoranthene-3-ylboronic acid (2.46 g, 10 mmol) in place of the triphenylene-2-ylboronic acid used in <step 1> of Preparation Example 5 of < The procedure of step 1> was followed to obtain 3-chloro-6- (fluoranthen-3-yl) -9H-carbazole.

¹ H-NMR: δ 7.09 (d, 1H), 7.37 (d, 1H), 7.50 (m, 3H), 7.66 (m, 4H), 7.89 (s, 1H), 8.00 (m, 3H), 8.42 ( d, 2H), 11.65 (s, 1H)

<Step 2> Synthesis of A-8

3-Chloro-6- (triphenylen-2-yl) -9H-carbazole used in <Step 2> of Preparation Example 5 3-chloro-6- (obtained in <Step 1> of Preparation Example 8 above Fluoranthen-3-yl) -9H-carbazole (4.01 g, 10 mmol) was used instead of (9,9-dimethyl-9H-fluoren-2-yl) boronic acid (4- (triphenylsilyl) A-8 was obtained by the same procedure as <Step 2> of Preparation Example 5 except for using phenyl) boronic acid (3.80 g, 10.0 mmol).

¹ H-NMR: δ 7.37 (m, 17H), 7.65 (m, 4H), 7.77 (m, 3H), 7.89 (m, 4H), 7.99 (m, 2H), 8.10 (d, 2H), 8.42 ( d, 2H), 11.66 (s, 1H)

[ Preparation  9] Synthesis of A-9

<Step 1> 4- (6- Chloro -9H- Carbazole -3 days)- N, N - Diphenylaniline  synthesis

Preparation Example 5 except that (4- (diphenylamino) phenyl) boronic acid (2.89 g, 10 mmol) was used instead of the triphenylene-2-ylboronic acid used in <Step 1> of Preparation Example 5 5 (6-chloro-9H-carbazol-3-yl) -N, N-diphenylaniline was obtained in the same manner as in <Step 1> of 5.

¹ H-NMR: δ 7.00 (m, 7H), 7.24 (m, 4H), 7.37 (d, 2H), 7.55 (m, 4H), 7.77 (d, 1H), 7.89 (s, 1H), 7.99 ( d, 1 H), 11.65 (s, 1 H)

Step 2 Synthesis of A-9

4- (6-chloro- obtained in <Step 1> of Preparation Example 9 instead of 3-chloro-6- (triphenylen-2-yl) -9H-carbazole used in <Step 2> of Preparation Example 5 9H-carbazol-3-yl) -N, N-diphenylaniline (4.44 g, 10 mmol) was used instead of (9,9-dimethyl-9H-fluoren-2-yl) boronic acid (7-phenyl A-9 was obtained by the same procedure as in <Step 2> of Preparation Example 5 except for using -7H-benzo [c] carbazol-10-yl) boronic acid (3.37 g, 10.0 mmol). .

¹ H-NMR: δ 7.00 (m, 7H), 7.24 (m, 4H), 7.37 (d, 2H), 7.55 (m, 11H), 7.77 (d, 2H), 7.90 (m, 6H), 8.13 ( d, 1H), 8.30 (d, 1H), 8.54 (d, 1H), 11.65 (s, 1H)

Preparation Example 10 Synthesis of A-10

<Step 1> N-([1,1'-biphenyl] -4-yl) -N- (4- (6- Chloro -9H- Carbazole Synthesis of -3-yl) phenyl) -9,9-dimethyl-9H-fluoren-2-amine

(4-([1,1'-biphenyl] -4-yl (9,9-dimethyl-9H-fluorene-) instead of the triphenylene-2-ylboronic acid used in <Step 1> of Preparation Example 5 Except for using 2-yl) amino) phenyl) boronic acid (4.81 g, 10 mmol), N-([1,1'-biphenyl) was carried out in the same manner as in <Step 1> of Preparation Example 5 above. ] -4-yl) -N- (4- (6-chloro-9H-carbazol-3-yl) phenyl) -9,9-dimethyl-9H-fluoren-2-amine.

¹ H-NMR: δ 1.69 (s, 6H), 7.11 (m, 2H), 7.55 (m, 17H), 7.77 (m, 3H), 7.89 (m, 3H), 7.99 (d, 1H), 11.67 ( s, 1 H)

<Step 2> Synthesis of A-10

N-([1,1] obtained in <Step 1> of Preparation Example 10 in place of the 3-chloro-6- (triphenylen-2-yl) -9H-carbazole used in <Step 2> of Preparation Example 5 '-Biphenyl] -4-yl) -N- (4- (6-chloro-9H-carbazol-3-yl) phenyl) -9,9-dimethyl-9H-fluoren-2-amine (6.37 g , 10 mmol), and (9-phenyl-9H-carbazol-3-yl) boronic acid (2.87 g, 10.0 mmol) instead of (9,9-dimethyl-9H-fluoren-2-yl) boronic acid. Except for using the same procedure as in <Step 2> of Preparation Example 5 to obtain A-10.

¹ H-NMR: δ 1.69 (s, 6H), 7.16 (m, 2H), 7.50 (m, 20H), 7.87 (m, 14H), 8.55 (d, 1H), 11.67 (s, 1H)

[ Preparation  11] Synthesis of A-11

Step 1 Synthesis of A-11

3-bromo-6-phenyl-9H-carbazole (3.22 g, 10 mmol), 11-phenyl-11,12-dihydroindolo [2,3-a] carbazole (3.32 g, 10 under nitrogen stream mmol), Pd (OAc) ₂ (0.22 g, 1 mmol), P ( t -Bu) ₃ (0.47 ml, 2 mmol), NaO ( t -Bu) (1.92 g, 20 mmol) and toluene (100 ml) Were mixed and stirred at 110 ° C. for 2 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the target compound A-11 (2.86 g, yield 50%).

¹ H-NMR: δ 7.16 (m, 2H), 7.50 (m, 17H), 7.90 (m, 4H), 8.12 (d, 1H), 8.55 (d, 2H), 11.66 (s, 1H)

[ Preparation  12] Synthesis of A-12

Step 1 Synthesis of A-12

3-bromo-6- (phenyl-d5) -9H-carbazole (3.27 g, 10 mmol) was used instead of the 3-bromo-6-phenyl-9H-carbazole used in <Step 1> of Preparation Example 11. 14H-benzo [c] benzo [4,5] thieno [2,3-a] carbazole (3.23 g) instead of 11-phenyl-11,12-dihydroindolo [2,3-a] carbazole , 10 mmol) was carried out in the same manner as in <Step 1> of Preparation Example 11, except that A-12 was obtained.

¹ H-NMR: δ 7.16 (t, 1H), 7.35 (m, 2H), 7.66 (m, 7H), 7.90 (m, 4H), 8.50 (m, 4H), 11.66 (s, 1H)

[ Preparation  13] Synthesis of A-13

<Step 1> Synthesis of A-13

Instead of 3-bromo-6-phenyl-9H-carbazole used in <Step 1> of Preparation Example 1, 3-bromo-9H-carbazole (2.46 g, 10 mmol) was used and [1,1'- Preparation Example 1 except that (4- (dibenzo [b, d] thiophen-4-yl) phenyl) boronic acid (3.04 g, 10 mmol) was used instead of biphenyl] -3-ylboronic acid. A-13 was obtained by the same procedure as in <Step 1>.

¹ H-NMR: δ 7.22 (m, 5H), 7.66 (m, 6H), 7.93 (m, 3H), 8.19 (d, 1H), 8.32 (d, 1H), 8.45 (d, 1H), 8.55 ( d, 1 H), 11.66 (s, 1 H)

[ Preparation  14] Synthesis of A-14

<Step 1> Synthesis of A-14

Instead of 3-bromo-6-phenyl-9H-carbazole used in <Step 1> of Preparation Example 1, 3-bromo-9H-carbazole (2.46 g, 10 mmol) was used and [1,1'- Preparation Example 1, except that (4- (dibenzo [b, d] furan-2-yl) phenyl) boronic acid (2.88 g, 10 mmol) was used instead of biphenyl] -3-ylboronic acid. A-14 was obtained by performing the same procedure as in <Step 1>.

¹ H-NMR: δ 7.40 (m, 9H), 7.63 (d, 1H), 7.77 (m, 5H), 7.99 (m, 2H), 8.19 (d, 1H), 11.64 (s, 1H)

[ Preparation  15] Synthesis of A-15

Step 1 Synthesis of A-15

Instead of 3-bromo-6-phenyl-9H-carbazole used in <Step 1> of Preparation Example 1, 3-bromo-9H-carbazole (2.46 g, 10 mmol) was used and [1,1'- Preparation Example except that (3- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) boronic acid (3.14 g, 10 mmol) was used instead of biphenyl] -3-ylboronic acid. A-15 was obtained by performing the same procedure as in <Step 1> of 1.

¹ H-NMR: δ 1.69 (s, 6H), 7.28 (m, 3H), 7.55 (m, 5H), 7.77 (m, 3H), 7.99 (m, 5H), 8.09 (d, 1H), 8.19 ( d, 1 H), 11.66 (s, 1 H)

[ Preparation  16] Synthesis of A-16

<Step 1> Synthesis of A-16

Instead of 3-bromo-6-phenyl-9H-carbazole used in <Step 1> of Preparation Example 1, 3-bromo-9H-carbazole (2.46 g, 10 mmol) was used and [1,1'- <Step 1> of Preparation Example 1, except that (3- (triphenylen-2-yl) phenyl) boronic acid (3.48 g, 10 mmol) was used instead of biphenyl] -3-ylboronic acid. The same procedure was followed to obtain A-16.

¹ H-NMR: δ 7.20 (t, 1H), 7.50 (m, 12H), 7.90 (m, 3H), 8.19 (d, 1H), 8.33 (d, 1H), 8.46 (m, 2H), 9.11 ( d, 1H), 9.60 (d, 1H), 11.66 (s, 1H)

[ Synthesis Example  1] Synthesis of J-1

A-1 (3.95 g, 10 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.88 g, 10 mmol), Pd (OAc under nitrogen stream ) ₂ (0.22 g, 1 mmol), P ( t -Bu) ₃ (0.47 ml, 2 mmol), NaO ( t -Bu) (1.92 g, 20 mmol) and toluene (400 ml) were mixed and at 110 ° C. Stir for 2 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the title compound J-1 (3.51 g, yield 50%).

[Mass]: 702

[ Synthesis Example  2] Synthesis of J-2

Use A-2 (3.95 g, 10.0 mmol) instead of A-1 and 2-([1,1 instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Synthesis Example 1 except using '-biphenyl] -4-yl) -4- (3-bromophenyl) -6-phenyl-1,3,5-triazine (4.64 g, 10.0 mmol) The same procedure as in the title compound J-2 (3.97 g, yield 51%) was obtained.

[Mass]: 778

[ Synthesis Example  3] Synthesis of J-3

Use A-3 (4.85 g, 10.0 mmol) instead of A-1 and 2- (3'-bromine instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Synthesis Example 1, except that parent- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.64 g, 10.0 mmol) was used The same procedure was followed to obtain the title compound J-3 (4.51 g, yield 52%).

[Mass]: 869.04

[ Synthesis Example  4] Synthesis of J-4

Use A-4 (5.01 g, 10.0 mmol) instead of A-1 and 4-([1,1 instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine The same procedure as in Synthesis Example 1 was carried out except that '-biphenyl] -4-yl) -6- (3-bromophenyl) -2-phenylpyrimidine (4.63 g, 10.0 mmol) was used. The compound J-4 (4.68 g, yield 53%) was obtained.

[Mass]: 884.11

[ Synthesis Example  5] Synthesis of J-5

A-5 (5.85 g, 10.0 mmol) was used instead of A-1 and 2-bromo-4, instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, Except for using 6-bis (3,5-dimethylphenyl) -1,3,5-triazine (3.68 g, 10.0 mmol) was subjected to the same process as in Synthesis Example 1 to J-5 ( 4.71 g, yield 54%) was obtained.

[Mass]: 873.12

[ Synthesis Example  6] Synthesis of J-6

Use A-6 (5.45 g, 10.0 mmol) instead of A-1 and 2- (4-bromo instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for using phenyl) -4,6-diphenyl-1,3,5-triazine (3.88 g, 10.0 mmol), the same procedure as in Synthesis Example 1 was carried out to provide the target compound J-6 (4.69 g , Yield 55%) was obtained.

[Mass]: 853.04

[ Synthesis Example  7] Synthesis of J-7

Use A-7 (7.09 g, 10.0 mmol) instead of A-1 and replace 4 '-(4-bromine with 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Morphenyl) -4,4 ''-di-tert-butyl-2,2 ': 6', 2 ''-terpyridine (5.00 g, 10.0 mmol) except for using the same procedure as in Synthesis Example 1 Was carried out to obtain the title compound J-7 (6.32 g, yield 56%).

[Mass]: 1129.46

[ Synthesis Example  8] Synthesis of J-8

A-8 (7.01 g, 10.0 mmol) instead of A-1 and 5-bromoisophthalonitrile instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for using (2.07 g, 10.0 mmol) and the same procedure as in Synthesis Example 1 to obtain the title compound J-8 (4.71 g, yield 57%).

[Mass]: 828.06

[ Synthesis Example  9] Synthesis of J-9

Use A-9 (7.01 g, 10.0 mmol) instead of A-1 and 2-bromo-4, instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, Except for using 6-bis (4- (trifluoromethyl) phenyl) -1,3,5-triazine (4.48 g, 10.0 mmol), the same procedure as in Synthesis Example 1 was conducted, to obtain the target compound J -9 (6.20 g, yield 58%) was obtained.

[Mass]: 1069.13

[ Synthesis Example  10] Synthesis of J-10

Use A-10 (8.44 g, 10.0 mmol) instead of A-1 and 5,5 '-(6 instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine The same procedure as in Synthesis Example 1 was carried out except that-(3-bromophenyl) -1,3,5-triazine-2,4-diyl) diquinoline (4.90 g, 10.0 mmol) was used. The compound J-10 (7.39 g, yield 59%) was obtained.

[Mass]: 1253.53

[ Synthesis Example  11] Synthesis of J-11

Use A-11 (5.73 g, 10.0 mmol) instead of A-1 and 4-bromo-2- instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for using fluorodibenzo [b, d] furan (2.65 g, 10.0 mmol) was carried out the same procedure as in Synthesis Example 1 to obtain the target compound J-11 (4.54 g, yield 60%).

[Mass]: 757.87

[ Synthesis Example  12] Synthesis of J-12

Use A-12 (5.69 g, 10.0 mmol) instead of A-1 and (4-bromophenyl) instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for using diphenylphosphine oxide (3.57 g, 10.0 mmol) was carried out the same procedure as in Synthesis Example 1 to obtain the target compound J-12 (4.99 g, 59% yield).

[Mass]: 846.01

[ Synthesis Example  13] Synthesis of J-13

Use A-13 (4.25 g, 10.0 mmol) instead of A-1 and 2-([1,1 instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Synthesis Example 1 except that '-biphenyl] -4-yl) -4- (4-bromophenyl) -6- (4-fluorophenyl) pyrimidine (4.81 g, 10.0 mmol) was used The same procedure was followed to obtain the target compound J-13 (4.79 g, yield 58%).

[Mass]: 826.01

[ Synthesis Example  14] Synthesis of J-14

Use A-14 (4.25 g, 10.0 mmol) instead of A-1 and 2-bromo-4- instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for using phenylquinazoline (2.85 g, 10.0 mmol) was carried out the same procedure as in Synthesis Example 1 to obtain the target compound J-14 (3.49 g, yield 57%).

[Mass]: 613.72

[ Synthesis Example  15] Synthesis of J-15

Use A-15 (4.35 g, 10.0 mmol) instead of A-1 and 2-bromo-4- instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine Except for using (4- (naphthalen-1-yl) phenyl) quinazolin (4.11 g, 10.0 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the target compound J-15 (4.28 g, yield 56% )

[Mass]: 765.96

[ Synthesis Example  16] Synthesis of J-16

Use A-16 (4.69 g, 10.0 mmol) instead of A-1 and 2-bromo-4, instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, Except for using 6-diphenyl-1,3,5-triazine (3.12 g, 10.0 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the target compound J-16 (3.85 g, yield 55%) Got.

[Mass]: 700.85

[ Synthesis Example  17] Synthesis of J-17

3-phenyl-9H-carbazole (2.43 g, 10.0 mmol) instead of A-1 and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- Except using (3'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (4.64 g, 10.0 mmol) Was carried out in the same manner as in Synthesis Example 1 to obtain J-17 (3.38 g, yield 54%) as a target compound.

[Mass]: 626.76

[ Synthesis Example  18] Synthesis of J-18

3-phenyl-9H-carbazole (2.43 g, 10.0 mmol) instead of A-1 and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3 ''-bromo- [1,1 ': 3', 1 ''-terphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (5.40 g, 10.0 Except for using mmol), the same procedure as in Synthesis Example 1 was performed to obtain J-18 (3.72 g, yield 53%) as a target compound.

[Mass]: 702.86

[ Synthesis Example  19] Synthesis of J-19

3-phenyl-9H-carbazole (2.43 g, 10.0 mmol) instead of A-1 and 4- (6-bromophenyl) -4,6-diphenyl-1,3,5-triazine instead of 4- ([1,1'-biphenyl] -4-yl) -6- (3'-bromo- [1,1'-biphenyl] -3-yl) -2-phenylpyrimidine (5.39 g, 10.0 Except for using mmol), the same procedure as in Synthesis Example 1 was carried out to obtain the target compound J-19 (3.64 g, yield 52%).

[Mass]: 701.87

[ Synthesis Example  20] Synthesis of J-20

3-([1,1'-biphenyl] -3-yl) -9H-carbazole (3.19 g, 10.0 mmol) instead of A-1 and 2- (3-bromophenyl) -4,6- 2- (4 ''-bromo- [1,1 ': 3', 1 ''-terphenyl] -4-yl) -4,6-diphenyl instead of diphenyl-1,3,5-triazine Except for using -1,3,5-triazine (5.40 g, 10.0 mmol) was carried out in the same manner as in Synthesis Example 1 to obtain the target compound J-20 (3.97 g, yield 51%).

[Mass]: 778.96

[ Synthesis Example  21] Synthesis of J-21

3-([1,1'-biphenyl] -4-yl) -9H-carbazole (3.19 g, 10.0 mmol) instead of A-1 and 2- (3-bromophenyl) -4,6- Except for using 2-bromo-4-phenylquinazoline (2.85 g, 10.0 mmol) instead of diphenyl-1,3,5-triazine, the same procedure as in Synthesis Example 1 was carried out to give the target compound J- 21 (2.61 g, yield 50%) was obtained.

[Mass]: 523.64

[ Example  1 to 18] organic Electric field  Fabrication of light emitting device

The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.

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

M-MTDATA (60 nm) / TCTA (80 nm) / 90% of the host compound + 10% Ir (ppy) ₃ (300nm) / BCP (10 nm) / Alq ₃ (30) nm) / LiF (1 nm) / Al (200 nm) were laminated to fabricate an organic EL device.

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

Comparative Example 1 Fabrication of Organic Electroluminescent Device

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound J-1 as the light emitting host material when the emission layer was formed.

[Evaluation Example]

For each organic electroluminescent device manufactured in Examples 1 to 18 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below.

Sample Host Drive voltage (V) Emission Peak (nm) Current efficiency (cd / A) Example 1 J-1 6.81 518 39.7 Example 2 J-2 6.68 518 38.9 Example 3 J-3 6.66 518 41.3 Example 4 J-4 6.7 517 41.3 Example 5 J-5 6.7 515 43.1 Example 6 J-6 6.51 518 43.5 Example 7 J-8 6.77 518 41.4 Example 8 J-11 6.46 518 42.2 Example 9 J-12 6.81 517 42 Example 10 J-13 6.68 515 41.8 Example 11 J-14 6.66 518 41.3 Example 12 J-15 6.48 518 41.2 Example 13 J-16 6.86 517 41.2 Example 14 J-17 6.77 515 41.4 Example 15 J-18 6.66 518 42.2 Example 16 J-19 6.81 518 39.7 Example 17 J-20 6.68 518 38.9 Example 18 J-21 6.66 518 41.3 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, when the compounds (J-1 to J-6, J-8, J-11 to J-21) according to the present invention were used as the light emitting layer of the green organic EL device (Example 1 18) Compared with the conventional green organic electroluminescent device (Comparative Example 1) using CBP, it can be seen that excellent performance is achieved in terms of efficiency and driving voltage.

The present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.

Claims (12)

Compound represented by the following formula (1): [Formula 1]

In Chemical Formula 1, L ₁ to L ₄ are each independently selected from the group consisting of a single bond, an arylene group having ₆ to ₁₈ carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms; Ar ₁ is C ₆ ~ C ₆₀ aryl group or a nuclear atoms of 5 to 60 heteroaryl group; The arylene group and heteroarylene group of L ₁ to L _4, the aryl group and heteroaryl group of Ar ₁ 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, 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ Alkyl Oxy group, C ₆ to C ₆₀ arylamine group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₁ to C ₄₀ alkylsilyl group, C ₁ to C ₄₀ alkyl Boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group When substituted or unsubstituted with one or more substituents selected, and substituted with a plurality of substituents, they may be the same or different from each other; Ar ₂ and Ar ₃ are each independently hydrogen or a substituent selected from the group represented by Formulas A-1 to A-24, but Ar ₂ and Ar ₃ are different from each other;

In Chemical Formulas A-1 to A-24, * Means the part where the bond is made; Z ₁ to Z ₅ are each independently N or C (R ₇ ); Y ₁ and Y ₂ are each independently selected from the group consisting of a single bond, C (R ₈ ) (R ₉ ), N (R ₁₀ ), O and S, but both Y ₁ and Y ₂ are not single bonds; m and n are each independently an integer from 0 to 4; l is an integer from 0 to 3; 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 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ 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 An arylphosphanyl group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group, and a C ₆ ~ C ₆₀ arylamine group may be selected from the group consisting of or adjacent to a condensed ring, R ₁ And when there are a plurality of R _{2 s} , they are the same or different from each other; R ₃ to R ₁₀ 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 ₃ ~ C ₄₀ cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C _5-60 heteroaryl group, C ₁ -C ₄₀ alkyloxy group, C _6- 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 ~ mono or diaryl phosphine of C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine or adjacent groups bond to which they are attached may form a fused ring, wherein When each of R ₇ to R ₁₀ plural is 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 of the above R ₁ to R ₁₀ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C Alkynyl group of ₂ to C ₄₀ , aryl group of C ₆ to C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C ₆ to C ₆₀ , alkyloxy group of C ₁ to C ₄₀ , C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ selected from the group consisting of C ₆₀ aryl silyl When substituted by one or more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other. The method of claim 1, The compound is a compound represented by the formula [Formula 2]

In Chemical Formula 2, Each of L ₁ to L ₄ and Ar ₁ to Ar ₃ are as defined in claim 1. The method of claim 1, L ₁ to L ₄ are each independently selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a naphthalenyl group, a fluorenyl group, and a carbazolyl group. The method of claim 1, Ar ₁ is a compound selected from the group represented by the following formula B-1 to B-9:

In Chemical Formulas B-1 to B-9, * Means the part where the bond is made; X ₁ to X ₈ are each independently N or C (R ₁₆ ); Any one of X ₁ to X ₄ connected to L ₂ in Formula B-2 is C (R ₁₆ ), wherein R ₁₆ is absent; T ₁ is O, S, N (R ₁₇ ), C (R ₁₈ ) (R ₁₉ ) or SO ₂ ; R ₁₁ , R ₁₄ to R ₁₉ 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 ₃ -C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ 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, mono or diaryl phosphine of C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ by groups bonded to selected or adjacent from the group consisting of an aryl amine of the C ₆₀ can form a condensed ring When there are a plurality of R _{16 s} , they are the same as or different from each other; q and r are each independently integers of 0 to 4; p is an integer from 0 to 3; R ₁₂ and R ₁₃ 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 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ 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 An arylphosphanyl group, a C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and a C ₆ ~ C ₆₀ arylamine group may be selected from the group or adjacent to combine with a condensed ring to form a condensed ring, R ₁₂ And when there are a plurality of R _{13 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, alkyl boron group, aryl of the above R ₁₁ to R ₁₉ Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C ₁ -C ₄₀ alkyl, halogen C ₁ -C ₄₀ alkyl, C ₂ ~ C ₄₀ alkenyl group, an aryloxy group of C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ of the C ₆₀ aryl phosphazene group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ aryl of C ₆₀ silyl When substituted by one or more substituent species selected from the group consisting of or being substituted by plural substituents Beach and ring, they may be the same or different from each other. The method of claim 1, Wherein Ar ₁ is The compound substituents selected from the group represented by the formula F-1 to F-26 to:

In Chemical Formulas F-1 to F-26, * Means the part where the bond is made; t and x are each independently an integer from 0 to 5; u, q and r are each independently integers of 0 to 4; v is an integer from 0 to 3; w is an integer from 0 to 2; R ₁₂ , R ₁₃ , R ₂₀ and R ₂₁ 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, 5 to 60 heteroaryl group of nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkyl boron groups, C ₆ to C ₆₀ aryl boron groups , C ₆ ~ C ₆₀ arylphosphanyl group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group selected from the group consisting of, or in combination with an adjacent group condensed ring Can be formed, and when R ₁₂ , R ₁₃ , R ₂₀ and R ₂₁ are each plural, they are the same as or different from each other; R _11, R ₁₆ to R ₁₉ 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, nuclear atom 5 ~ 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₃ ~ C ₄₀ cycloalkyl group, nucleus Heterocycloalkyl group having 3 to 40 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 arylphosphanyl group, C ₆ ~ C ₆₀ Mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ An arylsilyl group or selected from the group consisting of a condensed ring to combine with Can be; The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group and alkylsilyl group of R ₁₁ to R ₁₃ and R ₁₆ to R ₂₁ , Alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl 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 to C ₄₀ alkynyl group, C ₆ to C ₆₀ aryl group, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy group, C ₁ to C ₄₀ Alkoxyoxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ boron alkyl group, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group in the silyl made If true, and substituted or unsubstituted by one or more substituent species selected from the group, which is substituted with plural substituents, they may be the same or different from each other. The method of claim 4, wherein R ₁₁ to R ₁₆ are each independently selected from the group consisting of C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group of nuclear atoms. The method of claim 1, Wherein Ar ₂ and Ar ₃ are each independently hydrogen or a substituent selected from the group represented by Formulas A-5 and A-10 to A-24, but Ar ₂ and Ar ₃ are different from each other. The method of claim 1, The R ₁ to R ₃ are each independently selected from the group consisting of C ₁ ~ C ₁₀ alkyl group, C ₆ ~ C ₆₀ aryl group and 5 to 60 heteroaryl group of nuclear atoms. The method of claim 1, R ₄ to R ₆ are each independently hydrogen, a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ An aryl group and a nuclear atom of 5 to 60 heteroaryl group selected from the group consisting of. The method of claim 1, 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 material layer interposed between the anode and the cathode, At least one of the one or more organic material layer is an organic electroluminescent device, characterized in that it comprises a compound represented by the formula (1) of claim 1. The method of claim 11, The organic material layer including 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 improvement layer, a light emitting layer and a light emitting auxiliary layer.