KR20160058081A - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescence device comprising the same. The compound of the present invention can be used in an organic layer of the organic electroluminescence device, preferably in a luminescent layer thereof, thereby improving the luminescence efficiency, driving voltage and lifespan of the organic electroluminescence device.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic compound and an organic electroluminescent device including the organic compound.

The present invention relates to a novel organic compound that can be used as a material of an organic electroluminescent device, and an organic electroluminescent device including the same and having improved luminous efficiency, driving voltage, and life span of the device.

Studies on organic electroluminescent (EL) devices (hereinafter, simply referred to as 'organic EL devices') by blue electroluminescence using anthracene single crystals in 1965 have been carried out with reference to the observation of organic thin film luminosity of Bernanose in the 1950s . In 1987, a layered organic EL device was proposed by Tang divided into a hole layer and a functional layer of a light emitting layer. Thereafter, in order to make a high efficiency and high number of organic EL devices, each organic EL element has been developed into a form in which each organic EL element has been introduced into the EL element, leading to the development of specialized materials used therefor.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer in the anode, and electrons are injected into the organic layer in the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material and the like depending on its function.

The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials necessary for realizing better natural colors. Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material.

The dopant material can 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. Since the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as much as that of the fluorescent material, studies on phosphorescent host materials as well as phosphorescent dopants have been conducted.

Until now, NPB, BCP, and Alq ₃ have been widely known as a hole injecting layer, a hole transporting layer, a hole blocking layer, and an electron transporting layer. Anthracene derivatives as a light emitting material have been reported as fluorescent dopant / host materials. Particularly, phosphorescent materials which have a great advantage in terms of efficiency improvement of light emitting materials include Firpic, Ir (ppy) ₃ , (acac) Ir (btp) as a blue, green, ₂ or the like is used. Up to now, 4,4-dicarbazolybiphenyl (CBP) has shown excellent properties as a phosphorescent host material.

However, existing materials have an advantage in terms of light emission characteristics, but their thermal stability is lowered due to a low glass transition temperature, so that they are not satisfactory in terms of lifetime in OLED devices. Therefore, development of materials with higher performance is required.

An object of the present invention is to provide a novel organic compound which has a high glass transition temperature and is excellent in thermal stability and can improve the bonding force between holes and electrons.

It is another object of the present invention to provide an organic electroluminescent device including the novel organic compound and having improved driving voltage, luminous efficiency, and the like.

The present invention provides a compound represented by the following formula (1): < EMI ID =

In Formula 1,

R ₁ and R ₂ , R ₂ and R ₃ or at least one of R ₃ and R ₄ are condensed with each other to form a condensed ring represented by the following formula (2);

R ₅ and R ₆ , R ₆ and R ₇ or at least one of R ₇ and R ₈ are condensed with each other to form a condensed ring represented by the following formula 3;

In the above Formulas 2 and 3,

The dotted line is the part where the condensation occurs;

X is selected from ₁ to X ₄ are the same or different, each independently represent O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ),

Provided that at least one of X ₁ and X ₃ and at least one of X ₂ and X ₄ are each N (Ar ₁ ), and when a plurality of N (Ar ₁ ) s are the same or different from each other;

L is a single bond or a substituted or unsubstituted C ₆ -C ₆₀ arylene group and a substituted or unsubstituted heteroarylene group having 5 to 60 ring atoms;

Ar ₁ to Ar ₅ Are independently selected from the group consisting of hydrogen, deuterium (D), halogen, cyano, nitro, substituted or unsubstituted C ₁ -C ₄₀ alkyl, substituted or unsubstituted C ₆ -C ₄₀ An aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, a substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted Or an unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ ~ C ₄₀ group of the arylboronic, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted C ₆ ~ C _An arylsilyl group having 1 to ₄₀ carbon atoms, or may be bonded to an adjacent group to form a condensed ring;

R ₁ to R and the substituent, and R ₁₁ to R ₁₈ of ₈ do not form a condensed ring of the formula 2 or 3 are the same or different and are each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group , A substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, a substituted or unsubstituted C of ₆ ~ C ₄₀ of the aryloxy group, a substituted or unsubstituted C ₁ ~ C ₄₀ of the alkyloxy group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl amine group, a substituted or unsubstituted C ₁ ~ C ₄₀ An alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₄₀ arylboron group, a substituted or unsubstituted C ₆ to C ₄₀ arylphosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted arylsilyl line from the group consisting of a C ₆ ~ C ₄₀ ring Or in combination, or the adjacent group to which they are attached may form a condensed ring;

a and b are each an integer of 0 to 3, and when a and b are each an integer of 1 to 3, R ₉ and R ₁₀ are the same as or different from each other and each independently selected from the group consisting of deuterium (D), halogen, A nitro group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, a C ₆ ~ C ₄₀ of the aryloxy group, a substituted or unsubstituted C ₁ ~ C ₄₀ of the alkyloxy group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl amine group, a substituted or unsubstituted C ₁ ~ C _A substituted or unsubstituted C ₁ to C ₄₀ alkylsulfonyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₄₀ arylboron group, a substituted or unsubstituted C ₆ to C ₄₀ arylphosphine group , A substituted or unsubstituted C ₆ to C ₄₀ arylphosphine oxide group, and a substituted or unsubstituted C ₆ to C ₄₀ arylsilyl group, or May be bonded to adjacent groups to form a condensed ring. When R ₉ is plural, they may be the same or different. When R ₁₀ is plural, they may be the same or different;

A C ₆ to C ₆₀ arylene group and a heteroarylene group having 5 to 60 nucleus atoms in the L and a C ₁ to C ₄₀ alkyl group and a C ₂ to C ₄₀ alkyl group in R ₁ to R ₁₈ and Ar ₁ to Ar ₅ , _A C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ An alkyloxycarbonyl group, an alkyloxyl group, a C ₆ to C ₄₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl boron group, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ aryl phosphine oxide of a C ₄₀ group, and a C ₆ ~ C ₄₀ aryl silyl group, are each independently a heavy hydrogen of , A halogen, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ alkyloxy group, the aryl group of C ₆ ~ C ₄₀ Ah Group, an aryl boronic of C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C _40, and a may be substituted by one or more substituents selected from the group consisting of an aryl silyl group of the, in which the substituent Are plural, they may be the same or different from each other.

The organic electroluminescent device according to the present invention includes a cathode, an anode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes one or more organic compounds A light emitting device is provided.

At least one of the organic layers including the compound of Formula 1 may be selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, and a light emitting layer, and may be a light emitting layer. At this time, the compound represented by Formula 1 may be a green or red phosphorescent host material.

The compound represented by the formula (1) according to the present invention is excellent in thermal stability and phosphorescence properties and can be used as a material of an organic material layer of an organic electroluminescent 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 produce an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency and long life time, A full-color display panel having greatly improved performance and lifetime can be manufactured.

Hereinafter, the present invention will be described in detail.

<Novel compound>

The novel compounds according to the invention are prepared by condensing one of indole moieties, indene moieties, benzothiophene moieties, benzofuran moieties, benzoylol moieties and benzoselenophene moieties in a carbazole moiety And two condensed heteroaromatic ring moieties are directly connected to each other or connected to each other through a linker such as an arylene group to form a basic skeleton and various substituents are bonded to the basic skeleton. .

In general, carbazole moieties are widely used as materials for organic electroluminescence devices, particularly phosphorescent host materials. The carbazole moiety has a triple energy as large as 3.0 eV and a HOMO energy level as low as 6.0 eV and is mainly used for the blue phosphorescent host. Alternatively, the compound represented by Formula 1 of the present invention may be prepared by condensing one of indole moiety, indene moiety, benzothiophene moiety, benzofuran moiety, benzoylol moiety, and benzoselenophene moiety in a carbazole moiety , The triplet energy is less than 3.0 eV and the HOMO energy level rises, making the energy band gap suitable for the green / red phosphorescent host.

The compound represented by the formula (1) of the present invention may be introduced with various substituent groups in a condensed heteroaromatic ring-moiety structure in which a carbazole moiety is condensed with an indole moiety or the like. At this time, when the electron withdrawing group (EWG) having a high electron absorbing property is substituted for the condensed hetero aromatic ring moiety, since the carbazole structure in the condensed hetero aromatic ring moiety is an electron donor, (bipolar) property, thereby increasing the bonding strength between the hole and the electron. Therefore, it is not only advantageous as a host in the phosphorescent light-emitting layer but also can be applied to an electron transport layer material and an electron injection layer material. On the other hand, when the electron donating group (EDG) is introduced (bonded) to the condensed heteroaromatic cyclic moiety, the entire molecule increases the hole transporting ability, and the hole transporting layer and the hole injecting layer Can be applied.

 In addition, in the compound of formula (1), the two condensed heteroaromatic ring moieties are directly connected to each other or connected to each other through a linker (L) such as an arylene group, whereby the molecular weight is significantly increased while maintaining the above- The transition temperature (Tg) and the decomposed temperature (Td) can be improved. Accordingly, the compound for a conventional organic electroluminescence device such as CBP (4,4-dicarbazolylbiphenyl) . The compound represented by the general formula (1) of the present invention also has an effect of inhibiting crystallization of the organic material layer.

Therefore, when the compound of Chemical Formula 1 according to the present invention is used as a hole injecting / transporting layer material of an organic electroluminescent device or a blue, green and / or red phosphorescent host material, compared to a conventional organic material layer material (for example, CBP) The light emitting efficiency and lifetime of the organic electroluminescent device can be greatly improved. Further, such lifetime enhancement of the organic electroluminescent device can maximize the performance of the full color organic luminescent panel.

In the compound represented by Formula 1, L is a divalent group linker known in the art and is a single bond or a substituted or unsubstituted C ₆ to C ₆₀ arylene group, Or a heteroarylene group having 5 to 60 unsubstituted nuclear atoms, and may be preferably a single bond.

The L ₆ C ₆ to C ₆₀ arylene group and the heteroarylene group having 5 to 60 nuclear atoms are each independently selected from deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl , A C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, C ₆ ~ C ₄₀ aryl amine group, a C ₃ ~ C ₄₀ cycloalkyl group, the nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ alkyl boronic group, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ with an aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl one or more substituents selected from the group consisting of . At this time, when there are a plurality of substituents, they may be the same or different.

A C ₆ ~ C ₆₀ arylene group, for example, the nuclear atoms of 5 to 60 hetero arylene group, the phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, an indenyl group, a pyran tray carbonyl group, a carboxylic A thiophenylene group, a thiophenylene group, a pyridinylene group, a pyrrolylene group, a pyrrolylene group, a pyrrolylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, And the like, but are not limited thereto. These may be the same or different and each represents a hydrogen atom, a halogen atom, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 of the A C ₁ to C ₄₀ alkylsulfonyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, a C ₆ to C ₄₀ arylphosphine group, a C ₆ to C ₄₀ Arylphosphine oxide group, and arylsilyl group of C ₆ to C ₄₀ . When there are plural substituents, they may be the same or different.

In the compounds represented by formula (1) of the present invention, two condensed heteroaromatic ring moieties bonded through L may be the same or different from each other.

Specifically, at least one of R ₁ and R ₂ , R ₂ and R ₃ or R ₃ and R ₄ is fused together to form a condensed ring represented by Formula 2, and R ₅ and R ₆ , R ₆ And R _7, or at least one of R ₇ and R ₈ , are condensed with each other to form a condensed ring represented by Formula 3. In this case, the first condensed heteroaromatic ring moiety containing the condensed ring of Formula 2 and the second condensed heteroaromatic ring moiety containing the condensed ring of Formula 3 may be the same or different. have.

The first condensed heteroaromatic ring moiety may be represented by any one of the following formulas A-1 to A-6.

In the above Formulas A-1 to A-6,

X ₁ and X ₃ , R ₁ to R ₄ , R ₉ , R ₁₁ to R ₁₄ and a are the same as defined in the above formula (1).

The second condensed heteroaromatic cyclic moiety may be represented by any one of the following formulas (B-1) to (B-6).

In the above Formulas B-1 to B-6,

X ₂ and X ₄ , R ₅ to R ₈ , R ₁₀ , R ₁₅ to R ₁₈ and b are as defined in the above formula (1).

In Formula 1, X ₁ to X ₄ are the same or different, each independently represent O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and Si (Ar ₄₎ (Ar ₅ , Wherein at least one of X ₁ and X ₃ and at least one of X ₂ and X ₄ are both N (Ar ₁ ), and preferably all of X ₁ to X ₄ are N (Ar ₁ ) .

Ar ₁ to Ar ₅ Are independently selected from the group consisting of hydrogen, deuterium (D), halogen, cyano, nitro, substituted or unsubstituted C ₁ -C ₄₀ alkyl, substituted or unsubstituted C ₆ -C ₄₀ An aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms, a substituted or unsubstituted C ₆ to C ₄₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted Or an unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ ~ C ₄₀ group of the arylboronic, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted C ₆ ~ C Or an arylsilyl group having 1 to ₄₀ carbon atoms, or may be bonded to an adjacent group to form a condensed ring.

Preferably, Ar ₁ to Ar ₅ are the same or different from each other and each independently represents a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, And an unsubstituted C ₆ to C ₄₀ arylamine group.

In the above Ar ₁ to Ar ₅ , a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to the 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C aryl phosphine oxide groups of ₄₀ and C ₆ ~ C ₄₀ aryl silyl group, and each independently represent a deuterium, a halogen, cyano group, C ₁ ~ C ₄₀ alkyl, C alkenyl group of _{2 ~ C 40, C 2 ~} C 40 A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a 3 to 40 nuclear atoms heterocycloalkyl group, C ₁ ~ C ₄₀ of Kill silyl group, C ₁ ~ C ₄₀ group, the alkyl boron C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide of the group and a C ₆ ~ C _An arylsilyl group having 1 to ₄₀ carbon atoms, and when the substituent is plural, they may be the same or different from each other.

R ₁ to R and the substituent, and R ₁₁ to R ₁₈ of ₈ do not form a condensed ring of the formula 2 or 3 are the same or different and are each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group , A substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, a substituted or unsubstituted C of ₆ ~ C ₄₀ of the aryloxy group, a substituted or unsubstituted C ₁ ~ C ₄₀ of the alkyloxy group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl amine group, a substituted or unsubstituted C ₁ ~ C ₄₀ An alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₄₀ arylboron group, a substituted or unsubstituted C ₆ to C ₄₀ arylphosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine oxide group, and a substituted or unsubstituted arylsilyl line from the group consisting of a C ₆ ~ C ₄₀ ring Bond or, or adjacent groups of to may form a condensed ring.

Preferably, R ₁ to R ₈ are substituents which do not form a condensed ring of the above formula (2) or (3) and R ₁₁ to R ₁₈ are hydrogen, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted nucleus A heteroaryl group having 5 to 40 atoms, and a substituted or unsubstituted C ₆ to C ₄₀ arylamine group.

a and b each represent an integer of 0 to 3, and when a and b are each 0, hydrogen is not substituted by substituents R ₉ and R ₁₀ , and when a and b are each an integer of 1 to 3 , R ₉ and R ₁₀ are the same or different and each independently represent a deuterium (D), a halogen, a cyano group, a nitro group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group, a substituted or unsubstituted C ₆ ~ one another C ₄₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 40 heteroaryl group, a substituted or unsubstituted C ₆ ~ C ₄₀ of the aryloxy group, a substituted or unsubstituted C alkyloxy of ₁ ~ C ₄₀ A substituted or unsubstituted C ₆ to C ₄₀ arylamine group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₄₀ alkylboron group, hwandoen C ₆ ~ C ₄₀ aryl boron group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₄₀ aryl phosphine Id group and in combination a substituted or unsubstituted C ₆ ~ selected from the group consisting of C ₄₀ or aryl silyl, or adjacent groups which may form a condensed ring. When R ₉ is plural, they are the same as or different from each other, and when R ₁₀ is plural, they are the same or different from each other.

In the above R ₁ to R ₁₈ , a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, 40 heteroaryl group, C ₆ ~ C ₄₀ of the aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to the 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C aryl phosphine oxide groups of ₄₀ and C ₆ ~ C ₄₀ aryl silyl group, and each independently represent a deuterium, a halogen, cyano group, C ₁ ~ C ₄₀ alkyl, C alkenyl group of _{2 ~ C 40, C 2 ~} C 40 A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a 3 to 40 nuclear atoms heterocycloalkyl group, C ₁ ~ C ₄₀ of Kill silyl group, C ₁ ~ C ₄₀ group, the alkyl boron C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide of the group and a C ₆ ~ C _An arylsilyl group having 1 to ₄₀ carbon atoms, and when the substituent is plural, they may be the same or different from each other.

More preferably, Ar ₁ to Ar ₅ And R ₁ to R ₈ Formula 2 or 3 substituents, and R ₉ do not form a fused ring to R ₁₈ is hydrogen, or in the, or a substituent, but may be selected from S1 to S205 to, and the like.

Examples of the compound represented by the formula (1) according to the present invention include compounds represented by the following formulas (4) to (24), but are not limited thereto.

In the above formulas 4 to 24,

X ₁ to X ₄ , R ₁ to R ₁₈ , a and b are each as defined in formula (1).

Specific examples of the compound represented by the formula (1) according to the present invention include compounds represented by the following formulas (25) to (45), but are not limited thereto.

In the above Chemical Formulas 25 to 45,

A plurality of Ar ₁ are the same or different from each other, are as defined in formula (I).

More specific examples of the compound represented by the formula (1) according to the present invention include, but are not limited to, the following compounds C1 to C46.

In the present invention, "alkyl" is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, But is not limited thereto.

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

In the present invention, "alkynyl" is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include ethynyl, 2-propynyl, and the like, but are 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. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, it is understood that a form in which two or more rings are pendant or condensed with each other may be included, and further includes a condensed form with an aryl group. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

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

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

"Cycloalkyl" in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls 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 a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one of the carbons, preferably one to three carbons, Or &lt; RTI ID = 0.0 &gt; Se. &Lt; / RTI &gt; Examples of such heterocycloalkyls 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 40 carbon atoms.

In the present invention, the term "condensed rings" means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

The compounds of formula (1) of the present invention can be synthesized in various ways with reference to the following Synthesis Examples. Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

&Lt; Organic electroluminescent device &

The present invention also provides an organic electroluminescent device comprising the compound represented by the above-mentioned formula (1).

Specifically, the organic electroluminescent device according to the present invention includes an anode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes Include compounds represented by the above formula (1). At this time, the compounds may be used alone or in combination of two or more.

The one or more organic layers may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer, and at least one of the organic layers may include a compound represented by Formula 1. [ Preferably, the organic material layer containing the compound of Formula 1 may be a light emitting layer, particularly a phosphorescent light emitting layer.

According to an embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, and the host material may include the compound of the above formula (1). When the compound of Formula 1 is included in the light emitting layer material of the organic electroluminescent device, preferably blue, green, and red phosphorescent host materials, the bonding strength between holes and electrons in the light emitting layer increases, Efficiency (luminous efficiency and power efficiency), lifetime, luminance, driving voltage, and the like can be improved. The compound represented by 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.

The structure of the organic electroluminescent device according to the present invention is not particularly limited and may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially laminated. At least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include a compound represented by Formula 1, and preferably, the emitting layer includes a compound represented by Formula 1 . Specifically, the compound of Formula 1 may be used as a phosphorescent host material of the light emitting layer. An electron injection layer may be further stacked on the electron transport layer.

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 layers and an anode are sequentially laminated, and an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.

The organic electroluminescent device according to the present invention may be formed by using materials and methods known in the art, except that at least one layer (for example, a light emitting layer) of the organic material layer includes the compound represented by Formula 1 Other organic material layers and electrodes.

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 a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.

Non-limiting examples of usable cathode materials include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as 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.

Non-limiting examples of usable cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; And multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer are not particularly limited, and conventional materials known in the art can be used.

Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.

[Preparation Example 1] Synthesis of Compound BIC-1

<Step 1> Synthesis of 2- (5-chloro-2-nitrophenyl) -9-phenyl-9H-carbazole

9-phenyl-9H-carbazol-2-ylboronic acid (157.34 g, 548 mmol) and NaOH (5.48 g, 137 mmol) were added to a solution of 4-chloro-2-iodo-1-nitrobenzene (77.66 g, 274 mmol) and it was stirred for 12 hours in a mixture of _{THF / H 2 O (800 ml} / 400 ml) , and _{then, Pd (PPh 3) 4 (} 4.36 g, 5 mol%) 80 ℃ put in 40 ℃.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and then MgSO ₄ was added thereto, followed by filtration to obtain an organic layer. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain 114.8 g of 2- (5-chloro-2-nitrophenyl) , Yield: 73%).

^{1 H-NMR: δ 7.28 (} d, 2H), 7.53 (m, 6H), 7.80 (d, 2H), 7.93 (d, 1H), 8.23 (m, 3H), 8.56 (d, 1H)

<Step 2> Synthesis of compounds C-1 and C-2

9-phenyl-9H-carbazole (114.8 g, 400 mmol), triphenylphosphine (314 g, 1200 mmol) obtained in the above Step 1 and 1,2- dichlorobenzene (1200 ml) were mixed and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed and extraction was performed with dichloromethane to obtain an organic layer. The resulting organic layer was washed with MgSO ₄ and purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain Compound C-1 (34.48 g, yield 48% 17.24 g, yield: 23%).

Of ^{C-1 1 H-NMR:} δ 6.98 (d, 1H), 7.28 (d, 2H), 7.57 (m, 8H), 7.96 (d, 1H), 8.23 (d, 1H), 8.65 (d, 1H ), 11.72 (s, 1 H)

¹ H-NMR of the C-2: δ 7.11 (d , 1H), 7.54 (m, 11H), 7.98 (d, 1H), 8.57 (d, 1H), 11.72 (s, 1H)

&Lt; Step 3 > 11-phenyl-3- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl ) -11,12-dihydroindolo [2,3-a] carbazole

(34.48 g, 94 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-tetramethylpiperidine (prepared in Step 2 of Preparation Example 1) Pd (dppf) Cl ₂ (3.4 g, 4.7 mmol), KOAc (26.67 g, 282 mmol) and 1,4-dioxane (500 ml) were mixed, followed by stirring at 130 ° C for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO _4, and the residue was purified by column chromatography (Hexane: EA = 10: 1 (v / v) 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -11,12-dihydroindolo [2,3-a] carbazole (27.9 g, yield 65%).

¹ H-NMR:? 1.24 (s, 12H), 7.26 (d, IH), 7.63 (m, 8H), 7.95 s, 1 H)

<Step 4> Synthesis of Compound C-3

(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -11,12-dihydroindolo [2 , 3-a] carbazole (27.9 g, 61.1 mmol), iodobenzene (24.89 g, 122 mmol), Cu powder (2 g, 30 mmol), K 2 CO 3 (19 g, 138 mmol), and nitrobenzene (300 ml ) Were mixed and then stirred at 190 DEG C for 12 hours.

After completion of the reaction, nitrobenzene was removed, and the organic layer was separated with methylene chloride. Then, water was removed from the organic layer using MgSO ₄ . The solvent was removed from the organic layer from which the water had been removed and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain Compound C-3 (23.5 g, yield 72%).

^{1 H-NMR: δ 1.24 (} s, 12H), 7.26 (d, 1H), 7.63 (m, 2H), 7.68 (m, 12H), 7.98 (d, 2H), 8.22 (d, 1H), 8.57 ( d, 1 H)

<Step 5> Synthesis of Compound BIC-1

Compound C-1 (8.07 g, 22 mmol) obtained in Step 3 of Preparation Example 1, compound C-3 (23.5 g, 44 mmol) obtained in Step 4 of Preparation Example 1, K ₂ CO ₃ (9.12 g, 66 mmol) and THF / H ₂ O (200 ml / 100 ml) were mixed and Pd (PPh ₃ ) ₄ (1.27 g, 5 mol% Lt; / RTI &gt;

After completion of the reaction, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered to obtain an organic layer. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain Compound BIC-1 (7.38 g, yield 45%).

^{1 H NMR: δ 7.28 (m} , 4H), 7.56 (m, 17H), 7.68 (d, 1H), 7.78 (s, 2H), 7.93 (d, 4H), 8.16 (d, 3H), 8.56 (d , &Lt; / RTI &gt; 2H), 11.72 (s, 1H)

[Preparation Example 2] Synthesis of Compound BIC-2

<Step 1> Synthesis of 3- (5-chloro-2-nitrophenyl) -9-phenyl-9H-carbazole

Except that 9-phenyl-9H-carbazol-3-ylboronic acid (157.34 g, 548 mmol) was used in place of 9-phenyl-9H-carbazol-2-ylboronic acid used in Step 1 of Preparation Example 1 (5-chloro-2-nitrophenyl) -9-phenyl-9H-carbazole (126.8 g, yield 66%) was obtained in the same manner as in <Step 1> of Preparation Example 1.

^{1 H-NMR: δ 7.28 (} d, 2H), 7.53 (m, 5H), 7.73 (m, 3H), 7.93 (d, 2H), 8.25 (m, 2H), 8.56 (d, 1H)

<Step 2> Synthesis of compounds C-4 and C-5

(5-chloro-2-nitrophenyl) -9-phenyl-9H-carbazole obtained in Step 1 of Preparation Example 2 was used instead of 2- (5-chloro-2- (33.88 g, yield 50%) was obtained by carrying out the same processes as in [Step 2] of Preparation Example 1, except that 9-phenyl-9-phenyl-9H-carbazole (126.8 g, 318 mmol) ) And Compound C-5 (8.07 g, yield: 22%).

¹ H-NMR:? 7.07 (d, 1H), 7.53 (m, 11H), 7.96

Of the ^{C-5 1 H-NMR:} δ 7.07 (d, 1H), 7.28 (d, 2H), 7.63 (m, 9H), 7.93 (d, 1H), 8.56 (d, 1H), 11.72 (s, 1H )

<Step 3> Synthesis of 1-phenyl-6- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl ) -1,3-dihydroindolo [2,3-b] carbazole

Except that the compound C-4 (33.88 g, 106 mmol) obtained in <Step 2> of Preparation Example 2 was used instead of the compound C-1 used in <Step 3> of Preparation Example 1, Step 3] to obtain 1-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1,3-dihydroindolo [2,3- b ] carbazole (30.71 g, 67 mmol).

¹ H-NMR:? 1.24 (s, 12H), 7.26 (d, 1H), 7.52 (m, 11H), 7.95

<Step 4> Synthesis of Compound C-6

11-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -11,12-dihydroindolo [2,3 -a] carbazole instead of 1-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1,3-dihydroindolo (24.58 g, yield 68%) was obtained by carrying out the same procedure as <Step 4> of Preparation Example 1, except that [2,3-b] carbazole (30.71 g, 67 mmol) .

^{1 H-NMR: δ 1.24 (} s, 12H), 7.26 (d, 1H), 7.32 (m, 2H), 7.53 (m, 13H), 7.98 (d, 2H), 8.57 (d, 1H)

<Step 5> Synthesis of Compound BIC-2

Compound C-4 (8.44 g, 23 mmol) obtained in Step 2 of Preparation Example 2 was used instead of Compound C-1 and Compound C-3 used in Step 4 of Preparation Example 1, (7.38 g, yield 43%) was obtained by following the same procedure as <Step 4> of Preparation Example 1, except that the compound C-6 (24.58 g, 46 mmol) obtained in Step 4 was used. &Lt; / RTI >

^{1 H NMR: δ 7.53 (m} , 23H), 7.68 (d, 1H), 7.79 (s, 2H), 7.89 (d, 4H), 8.23 (d, 1H), 8.56 (d, 2H), 11.72 (s , 1H)

[Preparation Example 3] Synthesis of Compound BIC-3

(17.24 g, 25 mmol) obtained in Step 2 of Preparation Example 1 and Preparation Example 1 were used instead of the compounds C-1 and C-3 used in Step 4 of Preparation Example 1, The same procedure as in <Step 4> of Preparation Example 1 was conducted except that the compound C-3 (26.72 g, 50 mmol) obtained in <Step 4> of Preparation Example 1 was used to obtain 7.45 g of compound BIC-3 %).

^{1 H NMR: δ 7.48 (m} , 22H), 7.68 (d, 1H), 7.78 (s, 2H), 7.93 (d, 4H), 8.16 (d, 2H), 8.56 (d, 2H), 11.72 (s , 1H)

[Preparation Example 4] Synthesis of Compound BIC-4

Compound C-5 (8.07 g, 22 mmol) obtained in Step 2 of Preparation Example 2 and Preparation Example 1 were used instead of the compounds C-1 and C-3 used in Step 4 of Preparation Example 1, The same procedure as in <Step 4> of Preparation Example 1 was conducted, except that the compound C-3 (23.5 g, 44 mmol) obtained in <Step 4> of Preparation Example 1 was used to obtain Compound BIC-4 (7.23 g, yield 38 %).

^{1 H NMR: δ 7.28 (d} , 4H), 7.56 (m, 19H), 7.68 (d, 2H), 7.93 (d, 4H), 8.16 (d, 2H), 8.56 (d, 2H), 11.72 (s , 1H)

[Synthesis Example 1] Synthesis of Compound C1

Compound in a nitrogen stream BIC-1 (7.38 g, 10.00 mmol), bromobenzene (1.88 g, 12.0 mmol), Pd (dba) 2 (0.22 g, 0.4 mmol), (t-Bu) 3 P (0.12 g, 0.6 mmol ) And sodium tert-butoxide (2.88 g, 30.0 mmol) were added to toluene (100 ml) and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and then filtered with MgSO ₄ . After removing the solvent from the filtered organic layer, Compound C1 (6.6 g, 8.1 mmol, yield 81%) was obtained by column chromatography.

GC-Mass (calculated: 814.31 g / mol, measured: 814 g / mol)

[Synthesis Example 2] Synthesis of Compound C2

The procedure of Synthesis Example 1 was repeated except that 1-bromo-3,5-diphenylbenzene (3.71 g, 12.00 mmol) was used instead of bromobenzene used in Synthesis Example 1 to obtain Compound C-2 (7.54 g, yield 78%).

GC-Mass (calculated: 966.37 g / mol, measured: 967 g / mol)

[Synthesis Example 3] Synthesis of Compound C3

The procedure of Synthesis Example 1 was repeated except that 2-chloro-4,6-diphenyl-1,3,5-triazine (3.21 g, 12.00 mmol) was used instead of bromobenzene used in Synthesis Example 1, C-3 (8.04 g, yield 83%).

GC-Mass (calculated: 969.36 g / mol, measured: 970 g / mol)

[Synthesis Example 4] Synthesis of Compound C4

Except that 3-bromo-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole (5.72 g, 12.00 mmol) was used instead of bromobenzene used in Synthesis Example 1 Was subjected to the same procedure as in Synthesis Example 1 to obtain Compound C4 (9.3 g, yield 82%).

GC-Mass (calculated: 1134.42 g / mol, measured: 1134 g / mol)

[Synthesis Example 5] Synthesis of Compound C5

Compound C5 (8.22 g, yield 79%) was obtained in the same manner as in Synthesis Example 1, except that 2- (3-bromophenyl) triphenylene (4.58 g, 12.00 mmol) was used in place of bromobenzene used in Synthesis Example 1, &Lt; / RTI &gt;

GC-Mass (calculated: 1040.39 g / mol, measured: 1041 g / mol)

[Synthesis Example 6] Synthesis of Compound C6

(Biphenyl-4-yl) -N- (4-bromophenyl) biphenyl-4-amine (5.7 g, 12.00 mmol) was used in place of the bromobenzene used in Synthesis Example 1 Was carried out to obtain Compound C6 (9.16 g, yield 76%).

GC-Mass (theory: 1205.45 g / mol, measurement: 1205 g / mol)

[Synthesis Example 7] Synthesis of Compound C7

The procedure of Synthesis Example 1 was repeated except that 2-bromo-4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.92 g, 12.00 mmol) was used in place of the bromobenzene used in Synthesis Example 1 To obtain Compound C7 (7.9 g, yield 74%).

GC-Mass (theory: 1068.39 g / mol, measured: 1068 g / mol)

[Synthesis Example 8] Synthesis of Compound C8

Except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (4.64 g, 12.00 mmol) was used instead of bromobenzene used in Synthesis Example 1, To give compound C8 (7.52 g, yield 72%).

GC-Mass (calculated: 1045.36 g / mol, measured: 1045 g / mol)

[Synthesis Example 9] Synthesis of Compound C9

The procedure of Synthesis Example 1 was repeated except that 2- (3-bromophenyl) -4,6-diphenylpyrimidine (4.63 g, 12.00 mmol) was used instead of bromobenzene used in Synthesis Example 1 to obtain 7.83 g , Yield: 75%).

GC-Mass (calculated: 1044.39 g / mol, measured: 1044 g / mol)

[Synthesis Example 10] Synthesis of Compound C10

(6.67 g, 10.00 mmol) was used instead of the compound BIC-2 (2.67 g, 10.00 mmol) obtained in Preparation Example 2 instead of the compound BIC-1 used in Preparation Example 1, Yield: 82%).

GC-Mass (calculated: 814.31 g / mol, measured: 814 g / mol)

[Synthesis Example 11] Synthesis of Compound C11

Compound C11 (7.34 g, 10.00 mmol) was obtained by following the same procedure as in Synthesis Example 2, except that the compound BIC-2 (2.67 g, 10.00 mmol) obtained in Preparation Example 2 was used instead of the compound BIC- Yield: 76%).

GC-Mass (calculated: 966.37 g / mol, measured: 966 g / mol)

[Synthesis Example 12] Synthesis of Compound C21

The procedure of Synthesis Example 3 was repeated except that the compound BIC-3 (2.67 g, 10.00 mmol) obtained in Preparation Example 3 was used instead of the compound BIC-1 used in Synthesis Example 3 to obtain a compound C21 (7.75 g, Yield: 80%).

GC-Mass (calculated: 969.36 g / mol, measured: 969 g / mol)

[Synthesis Example 13] Synthesis of Compound C22

Compound C22 (8.96 g, 10.00 mmol) was obtained by following the same procedure as in Synthesis Example 4, except that the compound BIC-3 (2.67 g, 10.00 mmol) obtained in Preparation Example 3 was used instead of the compound BIC- Yield: 79%).

GC-Mass (calculated: 1134.42 g / mol, measured: 1134 g / mol)

[ Synthetic example  14] Synthesis of Compound C32

Compound C32 (8.63 g, 10.00 mmol) was obtained by following the same procedure as in Synthesis Example 5, except that the compound BIC-4 (2.67 g, 10.00 mmol) obtained in Preparation Example 4 was used instead of the compound BIC- Yield: 83%).

GC-Mass (calculated: 1040.36 g / mol, measured: 1040 g / mol)

[Synthesis Example 15] Synthesis of Compound C33

Compound C33 (8.38 g, 10.00 mmol) was obtained by following the same procedure as in Synthesis Example 6, except that the compound BIC-4 (2.67 g, 10.00 mmol) obtained in Preparation Example 4 was used instead of the compound BIC- Yield: 74%).

GC-Mass (calculated: 1133.45 g / mol, measured: 1133 g / mol)

[Example 1] Production of green organic EL device

Compound C1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and a green organic EL device was fabricated according to the following procedure.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.

(60 nm) / TCTA (80 nm) / compound C1 + 10% Ir (ppy) ₃ (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) synthesized in Synthesis Example 1 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic EL device.

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

[Example 2] - [Example 15] Production of green organic EL device

Same as Example 1 except that the compounds C2 to C11, C21, C22, C32, and C33 synthesized in Synthesis Examples 2 to 15, respectively, were used in place of the compound C1 used as the light emitting host material in the light emitting layer formation in Example 1 To prepare a green organic EL device.

[Comparative Example 1] Production of green organic EL device

A green organic EL device was fabricated in the same manner as in Example 1, except that CBP was used in place of the compound C1 used as a light emitting host material in the formation of the light emitting layer in Example 1. The structure of CBP used is as follows.

[Comparative Example 2] Production of green organic EL device

A green organic EL device was fabricated in the same manner as in Example 1, except that Ref-1 was used instead of the compound C1 used as a luminescent host material in Example 1. The structure of Ref-1 used is as follows.

[Evaluation Example 1]

The driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2 were measured for the green organic EL devices manufactured in Examples 1 to 15 and Comparative Examples 1 and 2, respectively, and the results are shown in Table 1 .

Sample Host The driving voltage (V) EL peak (nm) Current efficiency (cd / A) Example 1 C1 6.50 520 41.8 Example 2 C2 6.55 521 41.9 Example 3 C3 6.45 520 41.5 Example 4 C4 6.40 519 41.7 Example 5 C5 6.40 518 41.6 Example 6 C6 6.35 518 41.9 Example 7 C7 6.35 519 40.9 Example 8 C8 6.40 519 41.5 Example 9 C9 6.45 517 41.8 Example 10 C10 6.50 520 41.7 Example 11 C11 6.50 519 41.7 Example 12 C21 6.40 518 41.9 Example 13 C22 6.35 519 41.9 Example 14 C32 6.40 520 42.0 Example 15 C33 6.35 518 42.0 Comparative Example 1 CBP 6.93 516 38.2 Comparative Example 2 Ref-1 6.75 517 40.2

As shown in Table 1, the green organic EL devices of Examples 1 to 15, in which the compound according to the present invention was used as a light emitting layer of a green organic EL device, had green of Comparative Examples 1 and 2 using CBP and Ref- The organic EL device exhibited higher current efficiency and better driving voltage than the organic EL device.

Claims (6)

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

In Formula 1,
R ₁ and R ₂ , R ₂ and R ₃ or at least one of R ₃ and R ₄ are condensed with each other to form a condensed ring represented by the following formula (2);
R ₅ and R ₆ , R ₆ and R ₇ or at least one of R ₇ and R ₈ are condensed with each other to form a condensed ring represented by Formula 3;
(2)

(3)

R ₁ to R ₈ Formula 2 or 3 condensed substituents and R ₁₁ to R ₁₈ do not form a ring of the each independently hydrogen;
L is a single bond;
X ₁ to X ₄ are all N (Ar ₁ ), wherein three Ar ₁ are phenyl and the remaining Ar ₁ is selected from the group consisting of triazine, carbazole and quinazoline;
The triazine, carbazole and quinazoline in Ar ₁ are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamine group, A C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₄₀ arylboron group, A C ₆ to C ₄₀ arylphosphine group, a C ₆ to C ₄₀ arylphosphine oxide group, and a C ₆ to C ₄₀ arylsilyl group, wherein the substituent is a plurality of substituents , They may be the same or different from each other,
The heteroaryl group and the heterocycloalkyl group each independently have 1 to 3 hetero atoms, wherein the hetero atom is at least one selected from the group consisting of N, O, S and Se. The method according to claim 1,
Wherein the compound represented by the formula (1) is represented by any one of the following formulas (6) and (19):
[Chemical Formula 6]

[Chemical Formula 19]

In the above formulas (6) and (19)
X ₁ to X ₄ , R ₁ to R ₈ and R ₁₁ to R ₁₈ are as defined in claim 1, respectively. The method according to claim 1,
Wherein the compound represented by Formula 1 is represented by any one of the following Chemical Formulas 27 and 40:
(27)

(40)

In the above formulas (27) and (40)
A plurality of Ar &_lt; 1 &gt; s are the same as or different from each other and defined as in claim 1; The method according to claim 1,
Wherein the compound represented by Formula 1 is selected from the group consisting of the following compounds C3, C4, C7, C21, and C22.

A cathode, and at least one organic layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound according to any one of claims 1 to 4. 6. The method of claim 5,
Wherein at least one organic compound layer containing the compound is a phosphorescent light-emitting layer.