WO2016105161A2 - Organic compound and organic electroluminescent element comprising same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent element comprising same and, more particularly, to a novel carbazole-based compound having excellent thermal stability and phosphorescent properties and an organic electroluminescent element comprising same in one or more organic layers thereof and thus requiring a low driving voltage and having high luminous efficiency and improved lifespan characteristics.

Description

Organic compound and organic electroluminescent device comprising the same

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to a novel carbazole compound having excellent thermal stability and phosphorescence properties and the like, in one or more organic material layers, to provide a low driving voltage and high light emission. An organic electroluminescent device having efficiency and improved lifespan characteristics.

The organic electroluminescent (EL) device (hereinafter, simply referred to as 'organic EL device') of blue electroluminescence using anthracene single crystal was observed based on observation of Bernanose organic thin film emission in the 1950s. Research has continued. In 1987, Tang presented an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer. Since then, in order to make a high efficiency, long life organic EL device, it has evolved to introduce each characteristic organic material layer in the device, leading to the development of specialized materials used therein.

In the organic EL 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 layer forming material of the organic EL device may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize a better natural color, depending on the light emission color. 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 phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent material, research on phosphorescent host materials as well as phosphorescent dopants has 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 transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials. In particular, phosphorescent materials having a great advantage in terms of efficiency improvement among the light emitting materials are blue, green, and red dopant materials, such as Firpic, Ir (ppy) ₃ , and (acac) Ir (btp). Metal complex compounds containing Ir, such as ₂ , are used. To date, 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.

However, existing materials have advantages in terms of luminescence properties, but due to low glass transition temperature and low thermal stability, they are not satisfactory in terms of lifespan in OLED devices. Therefore, the development of a material with more excellent performance is calculated | required.

An object of the present invention is to provide a novel organic compound having a high glass transition temperature, excellent thermal stability, and capable of improving the bonding force between holes and electrons.

In addition, an object of the present invention is to provide an organic electroluminescent device including the novel organic compound exhibiting low driving voltage, high luminous efficiency and improved lifespan characteristics.

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,

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

L ₁ is selected from the group consisting of a single bond, an arylene group having ₆ to ₄₀ carbon atoms and a heteroarylene group having 5 to 40 nuclear atoms;

a, b, c and d are each independently an integer from 0 to 4;

e is an integer from 0 to 3;

f is an integer from 0 to 2;

Ar ₁ to Ar ₅ are each independently hydrogen, deuterium (D), halogen, cyano, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₆ ~ C ₆₀ aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy 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 alkylboron group, C ₆ -C ₆₀ arylboron group, C _1- alkylphosphonate of C ₄₀ pingi, C ₁ ~ C ₄₀ alkyl phosphonic blood group, C ₆ ~ C ₆₀ aryl phosphine pingi, mono- or diaryl phosphine of C ₆ ~ C ₆₀ blood group, and a C ₆ ~ C ₆₀ aryl It may be selected from the group consisting of silyl groups, or may combine with adjacent groups to form a condensed ring, and when there are a plurality of Ar ₁ to Ar ₅ , they are the same or different from each other;

R ₁ to R ₆ are each independently a heavy hydrogen (D), halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ of the Aryl group, a heteroaryl group of 5 to 40 nuclear atoms, an aryloxy group of C ₆ ~ C ₆₀ , an alkyloxy group of C ₁ ~ C ₄₀ , an arylamine group of C ₆ ~ C ₆₀ , C ₃ ~ C ₄₀ Cycloalkyl group of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ an alkyl phosphine group, C ₁ ~ C ₄₀ alkyl phosphonic blood group, C of ₆ ~ C ₆₀ aryl phosphine group, a mono- or diaryl phosphine of C ₆ ~ C ₆₀ blood group, and a C ₆ ~ aryl silyl group of C ₆₀ It may be selected from the group consisting of, or combine with an adjacent group to form a condensed ring, when each of R _{One To} R _{6 It} is the same or different from each other;

The arylene group and heteroarylene group of L ₁ and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, of Ar ₁ to Ar ₅ and R ₁ to R ₆ , Cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl boron group, alkyl phosphine group, alkyl phosphinyl group, aryl phosphine group, mono or diaryl phosphinyl group and aryl silyl group are each independently deuterium, halogen , Cyano 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 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, group C ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl group of boron, C ₁ ~ C ₄₀ alkyl phosphine group, C ₁ ~ C ₄₀ alkyl phosphonic Blood group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C substituted with one or more substituents selected from the ₆₀ arylsilyl group the group consisting of or being unsubstituted When substituted with a plurality of substituents, these may be the same or different from each other.

According to one preferred embodiment of the present invention, the compound represented by Formula 1 may be represented by any one of the following Formula 2 to Formula 7:

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 2 to 7,

L ₁ , X ₁ to X ₂ , R ₁ to R ₆ , Ar ₁ to Ar ₅ , a, b, c, d, e and f are each as defined in Chemical Formula 1.

According to one preferred embodiment of the present invention, in Formula 1 X ₁ and X ₂ are both N (Ar ₁ ), a plurality of Ar ₁ may be the same or different from each other.

According to one preferred embodiment of the present invention, in Formula 1 L ₁ may be a single bond, a phenylene group or a biphenylene group.

According to one preferred embodiment of the present invention, in Formula 1 Ar ₁ to Ar ₅ are each independently hydrogen, deuterium (D), C ₆ ~ C ₆₀ aryl group, nuclear atoms of 5 to 40 heteroaryl groups And R ₅ and R ₆ may both be hydrogen.

According to one preferred embodiment of the present invention, in Formula 1 R ₁ to R ₄ are each independently in the group consisting of deuterium (D), C ₆ ~ C ₆₀ aryl group, 5 to 40 heteroaryl groups of nuclear atoms Can be selected.

According to one preferred embodiment of the present invention, both e and f may be zero.

According to one preferred embodiment of the present invention, at least one of Ar ₁ to Ar ₅ and R ₁ to R ₄ in the formula (1) may be a substituent represented by the following formula (8):

[Formula 8]

In Chemical Formula 8,

* Means a moiety bonded to Formula 1;

L ₂ is selected from the group consisting of a single bond, an arylene group having ₆ to ₄₀ carbon atoms and a heteroarylene group having 5 to 40 nuclear atoms;

Z ₁ to Z ₅ are the same as or different from each other, and each independently N or C (R ₁₁ ), wherein at least one of Z ₁ to Z ₅ is N;

When there are a plurality of R _{11 s} , they are the same as or different from each other, and R ₁₁ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ Alkynyl group of ˜C ₄₀ , aryl group of C ₆ ˜C ₆₀ , heteroaryl group of 5 to 40 nuclear atoms, aryloxy group of C ₆ ˜C ₆₀ C ₁ ~ C ₄₀ alkyloxy group, C ₃ ˜C ₄₀ cycloalkyl groups, 3 to 40 heterocycloalkyl groups, C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C group of ₆₀ arylboronic, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ selected from the group consisting arylsilyl of C ₆₀ of, or by combining the adjacent tile Can form condensed rings;

An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group of R ₁₁ , a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₆₀ aryl group, 5 to 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ group At least one member selected from the group consisting of an aryl boron group, a C ₆ -C ₆₀ arylphosphine group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylsilyl group When substituted or unsubstituted with a substituent 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, the substituent represented by Formula 8 may be a substituent represented by any one of the following Formula A-1 to Formula A-15:

In Chemical Formulas A-1 to A-15,

* Means the part where the bond is made;

n is an integer of 0 to 4, and when n is 0, it means that hydrogen is not substituted with a substituent R ₂₁ , and when n is an integer of 1 to 4, R ₂₁ is deuterium, halogen, cyano group, nitro 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, nuclear atom of 3 to 40 heterocycloalkyl group, C ₆ Aryl group of ~ C ₆₀ , heteroaryl group of 5 to 40 nuclear atoms, aryloxy group of C ₆ ~ C ₆₀ C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphine group, C ₆ to C ₆₀ mono or diaryl phosphinyl group And it may be selected from the group consisting of C ₆ ~ C ₆₀ arylsilyl group, or by combining with an adjacent group to form a condensed ring, when there are a plurality of R ₂₁ They are the same or different from each other;

An alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group of R ₂₁ , The arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₆₀ aryl group, 5 to 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ group At least one member selected from the group consisting of an aryl boron group, a C ₆ -C ₆₀ arylphosphine group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylsilyl group When substituted or unsubstituted with a substituent, and substituted with a plurality of substituents, they are the same as or different from each other;

L ₂ and R ₁₁ are each as defined in Chemical Formula 8 above.

According to a preferred embodiment of the present invention, the substituent represented by any one of Formulas A-1 to A-5 is characterized in that it is selected from the group consisting of the following substituents:

In the substituent, * means a portion to which a bond is made.

The present invention also includes (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer is one of Formula 1 It provides an organic electroluminescent device characterized in that it comprises a compound.

According to one preferred embodiment of the present invention, at least one of the one or more organic material layer containing the compound of Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer and a light emitting layer, Preferably it may be a light emitting layer, more preferably the compound represented by the formula (1) may be used as a green or red phosphorescent host of the light emitting layer.

"Alkyl" as used herein means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.

In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

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

"Aryl" in the present invention means a monovalent substituent derived from a C6 to C60 aromatic hydrocarbon combined with a single ring or two or more rings. In addition, a form in which two or more rings are attached to each other (pendant) or condensed may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Heteroaryl" as used herein means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form in which the two or more rings are condensed with an aryl group. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 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 6 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 an alkyl having 1 to 40 carbon atoms, and linear, branched or cyclic structure It may include. Examples of 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" is meant herein 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" as used herein means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons of nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as 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 6 to 60 carbon atoms.

As used herein, the term “condensed ring” means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

Since the compound represented by Formula 1 according to the present invention has excellent thermal stability and phosphorescence properties, it may be used as a material of the organic material layer of the organic EL device.

In particular, when the compound represented by Formula 1 according to the present invention is used as a phosphorescent host material, it is possible to manufacture an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency and long life compared to the conventional host material, It also enables the manufacture of full color display panels with significantly improved performance and longevity.

The present invention provides a compound represented by Formula 1:

[Formula 1]

In Chemical Formula 1,

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

L ₁ is selected from the group consisting of a single bond, an arylene group having ₆ to ₄₀ carbon atoms and a heteroarylene group having 5 to 40 nuclear atoms;

a, b, c and d are each independently an integer from 0 to 4;

e is an integer from 0 to 3;

f is an integer from 0 to 2;

Ar ₁ to Ar ₅ are each independently hydrogen, deuterium (D), halogen, cyano, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₆ ~ C ₆₀ aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy 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 alkylboron group, C ₆ -C ₆₀ arylboron group, C _1- alkylphosphonate of C ₄₀ pingi, C ₁ ~ C ₄₀ alkyl phosphonic blood group, C ₆ ~ C ₆₀ aryl phosphine pingi, mono- or diaryl phosphine of C ₆ ~ C ₆₀ blood group, and a C ₆ ~ C ₆₀ aryl It may be selected from the group consisting of silyl groups, or may combine with adjacent groups to form a condensed ring, and when there are a plurality of Ar ₁ to Ar ₅ , they are the same or different from each other;

R ₁ to R ₆ are each independently a heavy hydrogen (D), halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ of the Aryl group, a heteroaryl group of 5 to 40 nuclear atoms, an aryloxy group of C ₆ ~ C ₆₀ , an alkyloxy group of C ₁ ~ C ₄₀ , an arylamine group of C ₆ ~ C ₆₀ , C ₃ ~ C ₄₀ Cycloalkyl group of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ an alkyl phosphine group, C ₁ ~ C ₄₀ alkyl phosphonic blood group, C of ₆ ~ C ₆₀ aryl phosphine group, a mono- or diaryl phosphine of C ₆ ~ C ₆₀ blood group, and a C ₆ ~ aryl silyl group of C ₆₀ It may be selected from the group consisting of, or combine with an adjacent group to form a condensed ring, when each of R _{One To} R _{6 It} is the same or different from each other;

The arylene group and heteroarylene group of L ₁ and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, of Ar ₁ to Ar ₅ and R ₁ to R ₆ , Cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl boron group, alkyl phosphine group, alkyl phosphinyl group, aryl phosphine group, mono or diaryl phosphinyl group and aryl silyl group are each independently deuterium, halogen , Cyano 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 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, group C ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl group of boron, C ₁ ~ C ₄₀ alkyl phosphine group, C ₁ ~ C ₄₀ alkyl phosphonic Blood group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C substituted with one or more substituents selected from the ₆₀ arylsilyl group the group consisting of or being unsubstituted When substituted with a plurality of substituents, these may be the same or different from each other.

Hereinafter, the present invention will be described in detail.

1. New Organic Compounds

The present invention relates to a novel carbazole compound having excellent thermal stability and phosphorescence properties, and more particularly, includes at least two carbazole moieties, and dibenzo moieties are bonded to form a basic skeleton. Provided is a compound having a structure in which various substituents are bonded to this basic skeleton. However, at this time, the coupling position thereof is not particularly limited.

Specifically, the novel organic compound provided by the present invention is characterized by represented by the following formula (1):

[Formula 1]

In Chemical Formula 1,

X ₁ and X ₂ are each independently selected from the group consisting of O, S, Se, N (Ar ₁ ), C (Ar ₂ ) (Ar ₃ ) and Si (Ar ₄ ) (Ar ₅ ), wherein X ₁ and At least one of X ₂ is N (Ar ₁ ), preferably X ₁ and X ₂ are both N (Ar ₁ ), and a plurality of Ar ₁ are the same as or different from each other;

L ₁ is a divalent (divalent) connecting group (linker) of the group known to the art, and is selected from a single bond, C ₆ ~ C ₄₀ arylene group and a nuclear atoms of 5 to 40 heteroarylene group the group consisting of, preferably Phenylene group, biphenylene group, naphthylene group, anthracenylene group, indenylene group, pyranthrenylene group, carbazolylene group, thiophenylene group, indolylene group, furinylene group, quinolinyl group, pyrroylene group , Imidazolylene group, oxazolylene group, thiazolylene group, triazolylene group, pyridinylene group and pyrimidinylene group, and more preferably a single bond, a phenylene group or a biphenylene group;

a, b, c and d are each independently an integer from 0 to 4;

e is an integer from 0 to 3, f is an integer from 0 to 2, preferably both e and f are 0;

Ar ₁ to Ar ₅ are each independently hydrogen, deuterium (D), halogen, cyano, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₆ ~ C ₆₀ aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy 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 alkylboron group, C ₆ -C ₆₀ arylboron group, C _1- alkylphosphonate of C ₄₀ pingi, C ₁ ~ C ₄₀ alkyl phosphonic blood group, C ₆ ~ C ₆₀ aryl phosphine pingi, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl It may be selected from the group consisting of groups, or may be combined with adjacent groups to form a condensed ring, and when there are a plurality of Ar ₁ to Ar ₅ , they are the same or different from each other, preferably Ar ₁ to Ar ₅ are each independently , Cattle, deuterium _{(D), C 6 ~ C} 60 aryl group, from 5 to 40 heteroaryl group is selected from the group consisting of nuclear atoms;

R ₁ to R ₆ are each independently a heavy hydrogen (D), halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ of the Aryl group, a heteroaryl group of 5 to 40 nuclear atoms, an aryloxy group of C ₆ ~ C ₆₀ , an alkyloxy group of C ₁ ~ C ₄₀ , an arylamine group of C ₆ ~ C ₆₀ , C ₃ ~ C ₄₀ Cycloalkyl group of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ an alkyl phosphine group, C ₁ ~ C ₄₀ alkyl phosphonic blood group, C of ₆ ~ C ₆₀ aryl phosphine group, a mono- or diaryl phosphine of C ₆ ~ C ₆₀ blood group, and a C ₆ ~ aryl silyl group of C ₆₀ It may be selected from the group consisting of, or combine with an adjacent group to form a condensed ring, when there are a plurality of each of R ₁ to R ₆ They are the same or different from each other, preferably R ₁ to R ₆ are each independently deuterium (D), An aryl group having ₆ to ₆₀ carbon atoms, and a heteroaryl group having 5 to 40 nuclear atoms;

The arylene group and heteroarylene group of L ₁ and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, of Ar ₁ to Ar ₅ and R ₁ to R ₆ , Cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl boron group, alkyl phosphine group, alkyl phosphinyl group, aryl phosphine group, mono or diaryl phosphinyl group and aryl silyl group are each independently deuterium, halogen , Cyano 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 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, group C ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl group of boron, C ₁ ~ C ₄₀ alkyl phosphine group, C ₁ ~ C ₄₀ alkyl phosphonic Blood group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C substituted with one or more substituents selected from the ₆₀ arylsilyl group the group consisting of or being unsubstituted When substituted with a plurality of substituents, these may be the same or different from each other.

The dibenzo moiety which may be included in the compound represented by Formula 1 of the present invention may be selected from the following structures.

Meanwhile, the carbazole moiety is variously used as a material for an organic EL device, in particular, a phosphorescent host material. The carbazole moiety has a high triplet energy of 3.0 eV and a low HOMO energy level of 6.0 eV, which is mainly used in blue phosphorescent hosts. Therefore, in the case of the compound represented by Formula 1 of the present invention in which two dibenzo moieties are bonded to one benzene ring of a carbazole moiety, the triplet energy is less than 3.0 eV, and the HOMO energy level is increased to increase energy. The band gap is suitable for blue / green / red phosphorescent hosts.

In addition, in the compound represented by Formula 1 of the present invention, a carbazole moiety and one of the dibenzo moieties are bonded to one benzene ring of a carbazole moiety to generate steric hinderance. Cause Therefore, the compound molecules are distorted to solve the problem of deterioration of the luminescence property due to π-π-stacking, thereby preventing the formation of excitation dimers (eximers), thereby improving the luminescence efficiency. do.

In addition, in the compound represented by Formula 1 of the present invention, the carbazole moiety has the characteristics of an electron donating group (EDG) having a large electron donating property. When an electron withdrawing group (EWG) is introduced at the position 9 of a carbazole moiety as a substituent, the compound of the present invention has a large electron absorbing group (EWG) and a large electron donating group. The entire molecule is bipolar, including all the electron donating groups (EDGs). Since the bipolar compound represented by Formula 1 of the present invention can increase the binding force between holes and electrons, the bipolar compound is not only advantageous as a host in the phosphorescent light emitting layer but also may be applied to a hole transport layer, a hole injection layer, and an electron transport layer.

On the other hand, the compound represented by the formula (1) of the present invention has a higher thermal stability than the conventional CBP (4,4-dicarbazolybiphenyl) as the molecular weight of the compound is significantly increased due to the substituent introduced into the molecule to improve the glass transition temperature Indicates. In addition, the compound represented by the formula (1) of the present invention is also effective in suppressing the crystallization of the organic material layer.

According to one preferred embodiment of the present invention, the compound represented by Formula 1 may be a compound represented by any one of the following Formula 2 to Formula 7:

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 2 to 7,

L ₁ , X ₁ to X ₂ , R ₁ to R ₆ , Ar ₁ to Ar ₅ , a, b, c, d, e and f are each as defined in Chemical Formula 1.

According to one preferred embodiment of the present invention, in Formula 1, at least one of Ar ₁ to Ar ₅ and R ₁ to R ₄ may be a substituent represented by the following formula (8).

[Formula 8]

In Chemical Formula 8,

* Means a moiety bonded to Formula 1;

L ₂ is selected from the group consisting of a single bond, an arylene group having ₆ to ₄₀ carbon atoms and a heteroarylene group having 5 to 40 nuclear atoms;

Z ₁ to Z ₅ are the same as or different from each other, and each independently N or C (R ₁₁ ), wherein at least one of Z ₁ to Z ₅ is N;

When the R ₁₁ multiple individuals, all of which are the same or different, R ₁₁ is heavy hydrogen, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₆₀ aryl group, 5 to 40 heteroaryl groups, C ₆ ~ C ₆₀ aryloxy group C ₁ ~ C ₄₀ alkyloxy group, C ₃ ~ C ₄₀ cyclo alkyl, nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl of C ₆₀ Boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphinyl group and C ₆ ~ C ₆₀ arylsilyl group or selected from the group consisting of a condensed ring in combination with Can form;

An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group of R ₁₁ , a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₆₀ aryl group, 5 to 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ group At least one member selected from the group consisting of an aryl boron group, a C ₆ -C ₆₀ arylphosphine group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylsilyl group When substituted or unsubstituted with a substituent 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, at least one of Ar ₁ to Ar ₅ and R ₁ to R ₄ in Formula 1 may be a substituent represented by any one of the following Formula A-1 to Formula A-15:

In Chemical Formulas A-1 to A-15,

* Means the part where the bond is made;

n is an integer of 0 to 4, and when n is 0, it means that hydrogen is not substituted with a substituent R ₂₁ , and when n is an integer of 1 to 4, R ₂₁ is deuterium, halogen, cyano group, nitro 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, nuclear atom of 3 to 40 heterocycloalkyl group, C ₆ Aryl group of ~ C ₆₀ , heteroaryl group of 5 to 40 nuclear atoms, aryloxy group of C ₆ ~ C ₆₀ C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphine group, C ₆ to C ₆₀ mono or diaryl phosphinyl group And it may be selected from the group consisting of C ₆ ~ C ₆₀ arylsilyl group, or by combining with an adjacent group to form a condensed ring, when there are a plurality of R ₂₁ They are the same or different from each other;

An alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group of R ₂₁ , The arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₆₀ aryl group, 5 to 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ group At least one member selected from the group consisting of an aryl boron group, a C ₆ -C ₆₀ arylphosphine group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylsilyl group When substituted or unsubstituted with a substituent, and substituted with a plurality of substituents, they are the same as or different from each other;

L ₂ and R ₁₁ are each as defined in Chemical Formula 8 above.

According to a preferred embodiment of the present invention, the substituent represented by any one of Formulas A-1 to A-15 is preferably selected from the group consisting of the following substituents. However, this is not particularly limited:

However, in the substituent, * means a part to which a bond is made.

According to one preferred embodiment of the present invention, the compound represented by Formula 1 of the present invention may be more specifically selected from the group consisting of the following compounds, but is not limited thereto:

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 organic electroluminescent device according to the present invention includes (i) an anode, (ii) a cathode and (iii) one or more organic material layers interposed between the anode and the cathode, At least one of the one or more organic material layers includes a compound represented by Chemical Formula 1. In this case, the compound represented by Formula 1 may be used alone, or two or more may be mixed and used.

According to one embodiment of the present invention, in the organic electroluminescent device, at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by the formula (1). Preferably, the organic material layer including the compound of Formula 1 may be a light emitting layer.

In addition, according to an example of the present invention, the light emitting layer of the organic EL device may include a host material, wherein the host material may include the compound of formula (1). As such, when the compound of Formula 1 is included as the light emitting layer material of the organic EL device, preferably blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency (luminescence efficiency and power efficiency), lifetime, brightness, driving voltage, and the like can be improved. The compound represented by Chemical Formula 1 may be included in the organic light emitting device as a green and / or red phosphorescent host, a fluorescent host, or a dopant material.

Here, the structure of the organic electroluminescent device 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 injection layer may be further stacked on the electron transport layer, and as described above, 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 may be represented by Formula 1 according to the present invention. It may include a compound.

In addition, the structure of the organic electroluminescent 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 electroluminescent device according to the present invention is formed by using materials and methods known in the art, except that at least one layer (eg, the light emitting layer) of the organic material layer is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming another organic layer and an electrode.

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.

On the other hand, a ceramic crucible having high thermal conductivity is used as a method of forming the organic layer of the organic electroluminescent device by vacuum deposition, and should be designed so that stepwise and continuous evaporation control is possible and no organic splashing occurs. As the temperature of the evaporation source is not properly raised, the organic material that reaches the evaporation temperature in an excessively short time is splashed, and the inlet of the evaporation source is blocked, and thus the deposition rate of the organic material is not constant and thus the desired thin film characteristics are not obtained. . In addition, there is a high possibility that the organic material will be discolored or discolored during deposition. The organic material has a characteristic of being deposited by melting or sublimation depending on the material. In the case of deposition by the sublimation method, the compound immediately forms a organic layer through a sublimation process in the solid state, whereas in the case of the melting method The solid is vaporized through the liquid to form an organic layer. In the melting method, since the material undergoes one more phase change than the sublimation method, it is difficult to control the deposition temperature or the uniformity. In this case, the compound represented by Chemical Formula 1 according to the present invention may be deposited by a sublimation method and may have uniform thin film properties, thereby improving light emission characteristics.

As a result, when the compound of Formula 1 according to the present invention is used as a hole injection / transport layer material or a blue, green and / or red phosphorescent host material, an electron injection / transport layer material of an organic electroluminescent device, For example, compared to CBP), the efficiency and lifespan of the organic EL device can be greatly improved. In addition, the lifespan of the organic EL device may maximize the performance of the full color OLED panel.

Meanwhile, 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 positive electrode material usable 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.

In addition, usable negative electrode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; And multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like.

In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, conventional materials known in the art may be used.

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

[ Preparation  One] TCZ Synthesis of -1

<Step 1> 1- Chloro -9-phenyl-9H-3,9'- Bicarbazole  synthesis

3-bromo-1-chloro-9-phenyl-9H-carbazole (17.8 g, 50.0 mmol), 9H-carbazole (8.35 g, 50.0 mmol), Pd ₂ (dba) ₃ (2.30 g, 2.5 mmol), (t-Bu) ₃ P (1.01 g, 5.0 mmol) and sodium tert-butoxide (14.7 g, 150.0 mmol) were added to 500 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using column chromatography to give the title compound 1-chloro-9-phenyl-9H-3,9'-bicarbazole (14.8 g, 67% yield).

Mass: [(M + H) ⁺ ]: 443

Elemental Analysis: C, 81.35; H, 4. 32; Cl, 8.00; N, 6.32

<Step 2> TCZ Synthesis of -1

1-chloro-9-phenyl-9H-3,9'-bicarbazole (13.3 g, 30.0 mmol), (9H-carbazol-3-yl) boronic acid (6.33 g, 30.0 mmol), K under nitrogen stream ₂ CO ₃ (12.8 g, 90.0 mmol), Pd (PPh ₃ ) ₄ (1.73 g, 5 mol%) and X-Phos (2.4 g, 5.00 mmol) were added to 250 ml / 120 ml of THF / H ₂ O at 90 ° C. Stir for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound TCZ-1 (10.5 g, 61% yield) by column chromatography.

Mass: [(M + H) ⁺ ]: 574

¹ H-NMR: δ 7.16 (m, 2H), 7.20 (m, 2H), 7.35 (m, 2H), 7.52 (m, 7H), 7.67 (m, 3H), 7.74 (m, 2H), 7.95 ( m, 4H), 8.19 (m, 2H), 8.52 (m, 2H), 11.54 (s, 1H)

[ Preparation  2] TCZ Synthesis of -2

<Step 1> TCZ Synthesis of -2

Same procedure as in <Step 2> of Preparation Example 1, except using (9H-carbazol-2-yl) boronic acid (6.33 g, 30.0 mmol) instead of (9H-carbazol-3-yl) boronic acid Was carried out to obtain TCZ-2 (11.2 g, yield 65%).

Mass: [(M + H) ⁺ ]: 574

¹ H-NMR: δ 7.19 (m, 4H), 7.35 (m, 2H), 7.54 (m, 7H), 7.62 (m, 3H), 7.75 (m, 2H), 7.94 (m, 3H), 8.19 ( m, 2H), 8.31 (t, 1H), 8.55 (m, 2H), 11.55 (s, 1H)

[ Preparation  3] TCZ Synthesis of -3

<Step 1> TCZ Synthesis of -3

Same procedure as in <Step 2> of Preparation Example 1, except using (9H-carbazol-4-yl) boronic acid (6.33 g, 30.0 mmol) instead of (9H-carbazol-3-yl) boronic acid Was carried out to give TCZ-3 (8.95 g, yield 52%).

Mass: [(M + H) ⁺ ]: 574

¹ H-NMR: δ 7.19 (m, 4H), 7.35 (m, 2H), 7.55 (m, 8H), 7.62 (m, 3H), 7.75 (m, 2H), 7.94 (m, 2H), 8.20 ( m, 2H), 8.54 (m, 2H), 11.56 (s, 1H)

[ Preparation  4] TCZ Synthesis of -4

<Step 1> 9- (4- Chlorodibenzo [b, d] thiophene 2-yl) -9H- Carbazole  synthesis

Preparation, except using 2-bromo-4-chlorodibenzo [b, d] thiophene (14.9 g, 50.0 mmol) instead of 3-bromo-1-chloro-9-phenyl-9H-carbazole The same procedure as in <Step 1> of Example 1 was performed to obtain 9- (4-chlorodibenzo [b, d] thiophen-2-yl) -9H-carbazole (14.6 g, yield 76%).

Mass: [(M + H) ⁺ ]: 384

Elemental Analysis: C, 75.09; H, 3.68; Cl, 9.23; N, 3.65; S, 8.35

<Step 2> TCZ Synthesis of -4

9- (4-chlorodibenzo [b, d] thiophen-2-yl) -9H-carbazole (11.5 g, 30.0 mmol instead of 1-chloro-9-phenyl-9H-3,9'-bicarbazole) Except for using), the same procedure as in <Step 2> of Preparation Example 1 was obtained to obtain TCZ-4 (10.2 g, yield 66%).

Mass: [(M + H) ⁺ ]: 515

¹ H-NMR: δ 7.18 (m, 3H), 7.35 (t, 1H), 7.51 (m, 5H), 7.63 (d, 1H), 7.77 (m, 2H), 7.92 (m, 4H), 8.00 ( s, 1H), 8.20 (m, 2H), 8.50 (m, 2H), 11.56 (s, 1H)

[ Preparation  5] TCZ Synthesis of -5

<Step 1> TCZ Synthesis of -5

9- (4-chlorodibenzo [b, d] thiophen-2-yl) -9H-carbazole (11.5 g, 30.0 mmol instead of 1-chloro-9-phenyl-9H-3,9'-bicarbazole) Except for using), the same procedure as in <Step 1> of Preparation Example 2 was carried out to obtain TCZ-5 (9.12 g, 59% yield).

Mass: [(M + H) ⁺ ]: 515

¹ H-NMR: δ 7.16 (t, 1H), 7.21 (m, 2H), 7.35 (t, 1H), 7.53 (m, 5H), 7.63 (d, 1H), 7.75 (m, 2H), 7.92 ( m, 3H), 8.01 (s, 1H), 8.20 (m, 2H), 8.31 (d, 1H), 8.50 (m, 2H), 11.55 (s, 1H)

[ Preparation  6] TCZ Synthesis of -6

<Step 1> TCZ Synthesis of -6

9- (4-chlorodibenzo [b, d] thiophen-2-yl) -9H-carbazole (11.5 g, 30.0 mmol instead of 1-chloro-9-phenyl-9H-3,9'-bicarbazole) Except for using), the same procedure as in <Step 1> of Preparation Example 3 was obtained to obtain TCZ-6 (7.57 g, yield 49%).

Mass: [(M + H) ⁺ ]: 515

¹ H-NMR: δ 7.19 (m, 3H), 7.35 (t, 1H), 7.52 (m, 6H), 7.64 (d, 1H), 7.77 (m, 2H), 7.93 (m, 3H), 8.00 ( s, 1H), 8.19 (m, 2H), 8.50 (m, 2H), 11.56 (s, 1H)

[ Preparation  7] TCZ Synthesis of -7

<Step 1> 9- (4- Chlorodibenzo [b, d] furan 2-yl) -9H- Carbazole  synthesis

Preparation example except for using 2-bromo-4-chlorodibenzo [b, d] furan (14.1 g, 50.0 mmol) instead of 3-bromo-1-chloro-9-phenyl-9H-carbazole 1- (4-chlorodibenzo [b, d] furan-2-yl) -9H-carbazole (13.1 g, yield 71%) was obtained in the same manner as in <Step 1>.

Mass: [(M + H) ⁺ ]: 368

Elemental Analysis: C, 78.37; H, 3. 84; Cl, 9.64; N, 3.81; O, 4.35

<Step 2> TCZ Synthesis of -7

9- (4-chlorodibenzo [b, d] furan-2-yl) -9H-carbazole (11.0 g, 30.0 mmol) instead of 1-chloro-9-phenyl-9H-3,9'-bicarbazole Except for using the same process as in <Step 2> of Preparation Example 1 to obtain TCZ-7 (8.38 g, yield 56%).

Mass: [(M + H) ⁺ ]: 499

¹ H-NMR: δ 7.19 (m, 3H), 7.35 (m, 3H), 7.52 (m, 4H), 7.62 (m, 2H), 7.71 (m, 2H), 7.93 (m, 4H), 8.19 ( m, 2H), 8.55 (d, 1H), 11.55 (s, 1H)

[ Preparation  8] TCZ Synthesis of -8

<Step 1> TCZ Synthesis of -8

9- (4-chlorodibenzo [b, d] furan-2-yl) -9H-carbazole (11.0 g, 30.0 mmol) instead of 1-chloro-9-phenyl-9H-3,9'-bicarbazole Except for using the same process as in <Step 1> of Preparation Example 2 to obtain a TCZ-8 (8.68 g, yield 58%).

Mass: [(M + H) ⁺ ]: 499

¹ H-NMR: δ 7.20 (m, 3H), 7.37 (m, 3H), 7.52 (m, 4H), 7.65 (m, 2H), 7.71 (m, 2H), 7.92 (m, 3H), 8.19 ( m, 2H), 8.31 (d, 1H), 8.55 (d, 1H), 11.55 (s, 1H)

[ Preparation  9] TCZ Synthesis of -9

<Step 1> TCZ Synthesis of -9

9- (4-chlorodibenzo [b, d] furan-2-yl) -9H-carbazole (11.0 g, 30.0 mmol) instead of 1-chloro-9-phenyl-9H-3,9'-bicarbazole Except for using the same process as in <Step 1> of Preparation Example 3 to obtain a TCZ-9 (6.59 g, 44% yield).

Mass: [(M + H) ⁺ ]: 499

¹ H-NMR: δ 7.19 (m, 3H), 7.33 (m, 3H), 7.55 (m, 5H), 7.65 (m, 2H), 7.71 (m, 2H), 7.93 (m, 3H), 8.20 ( m, 2H), 8.55 (d, 1H), 11.55 (s, 1H)

[ Preparation  10] TCZ Synthesis of -10

<Step 1> 9- (1- Chloro -9,9-dimethyl-9H- Fluorene -3-yl) -9H- Carbazole  synthesis

Except for using 3-bromo-1-chloro-9,9-dimethyl-9H-fluorene (15.4 g, 50.0 mmol) instead of 3-bromo-1-chloro-9-phenyl-9H-carbazole 9- (1-chloro-9,9-dimethyl-9H-fluoren-3-yl) -9H-carbazole (14.4 g, 73% yield) by the same process as in <Step 1> of Preparation Example 1 Got.

Mass: [(M + H) ⁺ ]: 394

Elemental Analysis: C, 82.33; H, 5. 12; Cl, 9.00; N, 3.56

<Step 2> TCZ Synthesis of -10

9- (1-chloro-9,9-dimethyl-9H-fluoren-3-yl) -9H-carbazole (11.8 g, instead of 1-chloro-9-phenyl-9H-3,9'-bicarbazole) TCZ-10 (8.03 g, Yield 51%) was obtained in the same manner as <Step 2> of Preparation Example 1, except that 30.0 mmol) was used.

Mass: [(M + H) ⁺ ]: 525

¹ H-NMR: δ 1.64 (s, 6H), 7.21 (m, 4H), 7.35 (m, 2H), 7.52 (m, 4H), 7.63 (d, 1H), 7.73 (m, 2H), 7.99 ( m, 5H), 8.21 (m, 2H), 8.52 (d, 1H), 11.56 (s, 1H)

[ Preparation  11] TCZ Synthesis of -11

<Step 1> 4- Bromo -2- Chloro -9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H- Carbazole  synthesis

4-Bromo-2-chloro-9H-carbazole (14.0 g, 50.0 mmol), NaH (1.2 g, 50.0 mmol) and DMF (150 ml) under nitrogen stream were mixed and stirred at room temperature for 10 minutes, followed by 2 -Chloro-4,6-diphenyl-1,3,5-triazine (13.4 g, 50.0 mmol) was added thereto and stirred at room temperature for 1 hour. After the reaction was completed, water was added, the solid compound was filtered, and then purified by column chromatography to give the title compound 4-bromo-2-chloro-9- (4,6-diphenyl-1,3,5-tri Azin-2-yl) -9H-carbazole (20.7 g, yield 81%) was obtained.

Mass: [(M + H) ⁺ ]: 511, 513

Elemental Analysis: C, 63.36; H, 3. 15; Br, 15.61; Cl, 6.93; N, 10.95

<Step 2> TCZ Synthesis of -11

4-bromo-2-chloro-9- (4,6-diphenyl-1,3,5-triazin-2-yl) instead of 3-bromo-1-chloro-9-phenyl-9H-carbazole TCZ-11 (10.4 g, Yield 58%) was obtained by the same procedure as <Step 1> of Preparation Example 1, except that -9H-carbazole (15.3 g, 30.0 mmol) was used.

Mass: [(M + H) ⁺ ]: 598

¹ H-NMR: δ 7.13 (s, 1H), 7.19 (m, 3H), 7.33 (m, 3H), 7.51 (m, 8H), 7.94 (m, 2H), 8.19 (d, 1H), 8.36 ( d, 4H), 8.55 (d, 1H)

[ Synthesis Example  1] Synthesis of C 21

TCZ-1 (5.74 g, 10.0 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 10.0 mmol), Pd ₂ (dba) ₃ (0.46 g) under nitrogen stream , 0.5 mmol), (t-Bu) ₃ P (0.20 g, 1.0 mmol) and sodium tert-butoxide (2.94 g, 30.0 mmol) were added to 500 ml toluene and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer using a column chromatography to give the title compound C 21 (6.20 g, yield 77%).

Mass: [(M + H) ⁺ ]: 805

[ Synthesis Example  2] Synthesis of C 23

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.44 g, 10.00 mmol instead of 2-chloro-4,6-diphenyl-1,3,5-triazine Except for using), the same procedure as in Synthesis Example 1 was performed to obtain C 23 (7.75 g, yield 88%) as a target compound.

Mass: [(M + H) ⁺ ]: 881

[ Synthesis Example  3] Synthesis of C 28

Except for using TCZ-2 (5.74 g, 10.00 mmol) instead of TCZ-1 was the same procedure as in Synthesis Example 1 to obtain the target compound C 28 (6.44 g, yield 80%).

Mass: [(M + H) ⁺ ]: 805

[ Synthesis Example  4] Synthesis of C 29

Except for using TCZ-2 (5.74 g, 10.00 mmol) instead of TCZ-1 was carried out the same procedure as in Synthesis Example 2 to obtain the title compound C 29 (7.14 g, 81% yield).

Mass: [(M + H) ⁺ ]: 881

[ Synthesis Example  5] Synthesis of C 30

Except for using TCZ-3 (5.74 g, 10.00 mmol) instead of TCZ-1 was the same procedure as in Synthesis Example 1 to obtain the target compound C 30 (5.64 g, yield 70%).

Mass: [(M + H) ⁺ ]: 805

[ Synthesis Example  6] Synthesis of C 51

Except for using TCZ-4 (5.15 g, 10.00 mmol) instead of TCZ-1 was the same procedure as in Synthesis Example 1 to obtain the target compound C 51 (5.37 g, 72% yield).

Mass: [(M + H) ⁺ ]: 746

[ Synthesis Example  7] Synthesis of C 53

Except for using TCZ-4 (5.15 g, 10.00 mmol) instead of TCZ-1 was the same procedure as in Synthesis Example 2 to obtain the target compound C 53 (6.49 g, yield 79%).

Mass: [(M + H) ⁺ ]: 822

[ Synthesis Example  8] Synthesis of C 58

Except for using TCZ-5 (5.15 g, 10.00 mmol) instead of TCZ-1 was the same procedure as in Synthesis Example 1 to obtain the target compound C 58 (5.30 g, yield 71%).

Mass: [(M + H) ⁺ ]: 746

[ Synthesis Example  9] Synthesis of C 59

Except for using TCZ-5 (5.15 g, 10.00 mmol) instead of TCZ-1 was the same procedure as in Synthesis Example 2 to obtain the target compound C 59 (6.74 g, 82% yield).

Mass: [(M + H) ⁺ ]: 822

[ Synthesis Example  10] Synthesis of C 60

Except for using TCZ-6 (5.15 g, 10.00 mmol) instead of TCZ-1 was the same procedure as in Synthesis Example 1 to obtain the target compound C 60 (5.30 g, yield 71%).

Mass: [(M + H) ⁺ ]: 746

[ Synthesis Example  11] Synthesis of C 81

Except for using TCZ-7 (4.99 g, 10.00 mmol) instead of TCZ-1 was the same procedure as in Synthesis Example 1 to obtain the target compound C 81 (5.40 g, 74% yield).

Mass: [(M + H) ⁺ ]: 730

[ Synthesis Example  12] Synthesis of C 83

Except for using TCZ-7 (4.99 g, 10.00 mmol) instead of TCZ-1 was the same procedure as in Synthesis Example 2 to obtain the target compound C 83 (6.69 g, 83% yield).

Mass: [(M + H) ⁺ ]: 806

[ Synthesis Example  13] Synthesis of C 88

Except for using TCZ-8 (4.99 g, 10.00 mmol) instead of TCZ-1 was carried out the same procedure as in Synthesis Example 1 to obtain the target compound C 88 (5.11 g, yield 70%).

Mass: [(M + H) ⁺ ]: 730

[ Synthesis Example  14] Synthesis of C 89

Except for using TCZ-8 (4.99 g, 10.00 mmol) instead of TCZ-1 was the same procedure as in Synthesis Example 2 to obtain the target compound C 89 (7.01 g, 87% yield).

Mass: [(M + H) ⁺ ]: 806

[ Synthesis Example  15] Synthesis of C 90

Except for using TCZ-9 (4.99 g, 10.00 mmol) instead of TCZ-1 was the same procedure as in Synthesis Example 1 to obtain the title compound C 90 (5.26 g, 72% yield).

Mass: [(M + H) ⁺ ]: 730

[ Synthesis Example  16] Synthesis of C 111

Except for using TCZ-10 (5.25 g, 10.00 mmol) instead of TCZ-1 was carried out the same procedure as in Synthesis Example 1 to obtain the target compound C 111 (5.37 g, yield 71%).

Mass: [(M + H) ⁺ ]: 756

[ Synthesis Example  17] Synthesis of C 113

Except for using TCZ-10 (5.25 g, 10.00 mmol) instead of TCZ-1 was carried out the same procedure as in Synthesis Example 2 to obtain the target compound C 113 (6.41 g, yield 77%).

Mass: [(M + H) ⁺ ]: 832

[ Synthesis Example  18] Synthesis of C 123

TCZ-11 (5.98 g, 10.0 mmol), (9-phenyl-9H-carbazol-3-yl) boronic acid (2.87 g, 30.0 mmol), K ₂ CO ₃ under nitrogen stream (4.27 g, 30.0 mmol), Pd (PPh ₃ ) ₄ (0.58 g, 5 mol%) and X-Phos (0.8 g, 5.00 mmol) were added with 120 ml / 40 ml / 40 ml of Tol / EtOH / H ₂ O and stirred at 90 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound C 123 (4.51 g, yield 56%) by column chromatography.

Mass: [(M + H) ⁺ ]: 805

[ Example  1 to 18] Fabrication of Green Organic EL Devices

Compounds C 21 to C 123 synthesized in Synthesis Examples 1 to 18 were subjected to high purity sublimation purification by a conventionally known method, and then green organic EL devices were manufactured according to the following procedure.

First, a 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. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.

M-MTDATA (60 nm) / TCTA (80 nm) / C 21 to C 123 each compound + 10% Ir (ppy) ₃ (30nm) / BCP (10 nm) / Alq ₃ ( An organic EL device was fabricated by stacking in the order of 30 nm) / LiF (1 nm) / Al (200 nm).

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

[ Comparative example  1] Fabrication of Green Organic EL Devices

A green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound C 21 as a light emitting host material when forming the emission layer.

[ Evaluation example ]

For each of the green organic EL devices produced in Examples 1 to 18 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at current density (10) mA / cm 2 were measured, and the results are shown in Table 1 below. It was.

Sample Host Drive voltage (V) EL peak (nm) Current efficiency (cd / A) Example 1 C 21 6.61 518 38.6 Example 2 C 23 6.70 517 39.3 Example 3 C 28 6.49 518 38.5 Example 4 C 29 6.81 518 39.9 Example 5 C 30 6.73 517 40.2 Example 6 C 51 6.74 518 40.8 Example 7 C 53 6.77 518 40.7 Example 8 C 58 6.71 516 39.2 Example 9 C 59 6.68 517 39.8 Example 10 C 60 6.63 517 39.4 Example 11 C 81 6.49 518 38.5 Example 12 C 83 6.87 517 39.1 Example 13 C 88 6.66 517 41.3 Example 14 C 89 6.70 517 40.4 Example 15 C 90 6.82 517 42.2 Example 16 C 111 6.81 518 41.5 Example 17 C 113 6.82 518 41.7 Example 18 C 123 6.81 518 39.6 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1 above, when the compounds (C 21 to C 123) according to the present invention were used as the light emitting layer of the green organic EL device (Examples 1 to 18), the green organic EL device using the conventional CBP (Comparative Example 1 Compared with), it shows better performance in terms of efficiency and driving voltage.

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to a novel carbazole compound having excellent thermal stability and phosphorescence properties and the like, in one or more organic material layers, to provide a low driving voltage and high light emission. An organic electroluminescent device having efficiency and improved lifespan characteristics.

Claims (13)

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

In Chemical Formula 1, X ₁ and X ₂ are each independently selected from the group consisting of O, S, Se, N (Ar ₁ ), C (Ar ₂ ) (Ar ₃ ) and Si (Ar ₄ ) (Ar ₅ ), wherein X ₁ to At least one of X ₂ is N (Ar ₁ ); L ₁ is selected from the group consisting of a single bond, an arylene group having ₆ to ₄₀ carbon atoms and a heteroarylene group having 5 to 40 nuclear atoms; a, b, c and d are each independently an integer from 0 to 4; e is an integer from 0 to 3; f is an integer from 0 to 2; Ar ₁ to Ar ₅ are each independently hydrogen, deuterium (D), halogen, cyano, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₆ ~ C ₆₀ aryl group, nuclear atom 5 to 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy 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 alkylboron group, C ₆ -C ₆₀ arylboron group, C _1- alkylphosphonate of C ₄₀ pingi, C ₁ ~ C ₄₀ alkyl phosphonic blood group, C ₆ ~ C ₆₀ aryl phosphine pingi, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl Selected from the group consisting of groups, or combine with adjacent groups to form a condensed ring, wherein each of Ar ₁ to Ar ₅ is the same or different from each other; R ₁ to R ₆ are each independently a heavy hydrogen (D), halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ of the Aryl group, a heteroaryl group of 5 to 40 nuclear atoms, an aryloxy group of C ₆ ~ C ₆₀ , an alkyloxy group of C ₁ ~ C ₄₀ , an arylamine group of C ₆ ~ C ₆₀ , C ₃ ~ C ₄₀ Cycloalkyl group of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₁ ~ C ₄₀ an alkyl phosphine group, C ₁ ~ C ₄₀ alkyl phosphonic blood group, C of ₆ ~ C ₆₀ aryl phosphine group, a mono- or diaryl phosphine of C ₆ ~ C ₆₀ blood group, and a C ₆ ~ aryl silyl group of C ₆₀ It may be selected from the group consisting of, or combine with an adjacent group to form a condensed ring, when each of R _{One To} R _{6 It} is the same or different from each other; The arylene group and heteroarylene group of L ₁ and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, of Ar ₁ to Ar ₅ and R ₁ to R ₆ , Cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkyl boron group, aryl boron group, alkyl phosphine group, alkyl phosphinyl group, aryl phosphine group, mono or diaryl phosphinyl group and aryl silyl group are each independently deuterium, halogen , Cyano 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 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, group C ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl group of boron, C ₁ ~ C ₄₀ alkyl phosphine group, C ₁ ~ C ₄₀ alkyl phosphonic Blood group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C substituted with one or more substituents selected from the ₆₀ arylsilyl group the group consisting of or being unsubstituted , When substituted with a plurality of substituents, they are the same or different from each other. The method of claim 1, Compound represented by the formula (1) is a compound characterized in that the compound represented by any one of the following formulas (2) to (7): [Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 2 to 7, L ₁ , X ₁ to X ₂ , R ₁ to R ₆ , Ar ₁ to Ar ₅ and a to f are each as defined in claim 1. The method of claim 1, X ₁ and X ₂ are both N (Ar ₁ ), and a plurality of Ar ₁ are the same or different from each other. The method of claim 1, L ₁ is a single bond, a phenylene group or a compound, characterized in that a biphenylene group. The method of claim 1, Ar ₁ to Ar ₅ are each independently selected from the group consisting of hydrogen, deuterium (D), a C ₆ -C ₆₀ aryl group and a heteroaryl group of 5-40 nuclear atoms; R ₁ to R ₄ are each independently selected from the group consisting of deuterium (D), a C ₆ to C ₆₀ aryl group and a heteroaryl group of 5 to 40 nuclear atoms; e and f are both 0. The method of claim 1, At least one of Ar ₁ to Ar ₅ and R ₁ to R ₄ may be a substituent represented by Formula 8 below: [Formula 8]

In Chemical Formula 8, * Means a moiety bonded to Formula 1; L ₂ is selected from the group consisting of a single bond, an arylene group having ₆ to ₄₀ carbon atoms and a heteroarylene group having 5 to 40 nuclear atoms; Z ₁ to Z ₅ are the same as or different from each other, and each independently N or C (R ₁₁ ), wherein at least one of Z ₁ to Z ₅ is N; When there are a plurality of R _{11 s} , they are the same as or different from each other, R ₁₁ is hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ Alkynyl group of C ₄₀ , aryl group of C ₆ ~ C ₆₀ , heteroaryl group of 5 to 40 nuclear atoms, aryloxy group of C ₆ ~ C ₆₀ , alkyloxy group of C ₁ ~ C ₄₀ , C ₃ ~ C ₄₀ Cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ arylamine group, C ₁ ~ C ₄₀ Alkylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or the adjacent groups bonded fused to the To form a ring; An alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group of R ₁₁ , a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₆₀ aryl group, 5 to 40 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ group At least one member selected from the group consisting of an aryl boron group, a C ₆ -C ₆₀ arylphosphine group, a C ₆ -C ₆₀ mono or diarylphosphinyl group, and a C ₆ -C ₆₀ arylsilyl group When substituted or unsubstituted with a substituent and substituted with a plurality of substituents, they are the same as or different from each other. The method of claim 6, Substituent represented by the formula (8) is a compound characterized in that the substituent represented by any one of formulas A-1 to A-15:

In Chemical Formulas A-1 to A-15, * Means the part where the bond is made; n is an integer of 0 to 4, and when n is 0, it means that hydrogen is not substituted with a substituent R ₂₁ , and when n is an integer of 1 to 4, R ₂₁ is deuterium, halogen, cyano group, nitro 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, nuclear atom of 3 to 40 heterocycloalkyl group, C ₆ Aryl group of ~ C ₆₀ , heteroaryl group of 5 to 40 nuclear atoms, aryloxy group of C ₆ ~ C ₆₀ C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ arylamine group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ to C ₄₀ alkyl boron group, C ₆ to C ₆₀ aryl boron group, C ₆ to C ₆₀ arylphosphine group, C ₆ to C ₆₀ mono or diaryl phosphinyl group And it is selected from the group consisting of C ₆ ~ C ₆₀ arylsilyl group, or combine with an adjacent group to form a condensed ring, when there are a plurality of R ₂₁ They are the same or different from each other; An alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group of R ₂₁ , The arylphosphine group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group of 5 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a C ₃ to C ₄₀ heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ group aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of Substituted with ventilation or unsubstituted and, if substituted with a plurality of substituents, they are same or different from each other; L ₂ and R ₁₁ are each as defined in claim 6. The method of claim 7, wherein Substituent represented by any one of the formula A-1 to A-5 is a compound, characterized in that selected from the group consisting of the following substituents:

In the substituent, * means a portion to which a bond is made. The method of claim 1, Compound represented by the formula (1) is characterized in that the compound selected from the group consisting of:

(i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, At least one of the one or more organic material layers comprises the compound according to any one of claims 1 to 9. The method of claim 10, The organic material layer including the compound represented by Formula 1 is selected from the group consisting of a light emitting layer, a light emitting auxiliary layer, a hole transport layer, a hole injection layer, an electron transport layer and an electron injection layer. The method of claim 11, The organic light emitting device comprising the compound represented by the formula (1) is a light emitting layer. The method of claim 12, The compound is an organic electroluminescent device used as a phosphorescent host of the light emitting layer.