KR101576570B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device including the same. More specifically, the present invention relates to an organic electroluminescent device using an indolophenanthridine compound as a host material, An organic electroluminescent device can be provided.

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.

(Electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') that led to blue electroluminescence using anthracene single crystals in 1965, starting from the observation of the organic thin film emission 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. At this time, since the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent material, researches 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. In particular, the phosphor has a great advantage in improving the efficiency aspects of the light-emitting material materials _{Firpic, Ir (ppy) 3,} (acac) Ir (btp) 2 Ir metal complex compound is blue (blue), which includes the same as the green ( green and red dopant materials, and CBP is a phosphorescent host material.

However, existing materials have an advantage in terms of luminescence properties, but their thermal stability is not very good due to their 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 capable of improving the bonding force between holes and electrons while having excellent thermal stability due to a high glass transition temperature.

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,

At least one of R ₁ and R ₂ , R ₂ and R _3, or at least one of R ₃ and R ₄ is bonded to the following formula 2 to form a condensed ring,

In the formula (2), the dotted line represents a site where condensation is performed with the compound of the formula (1)

X ₁ is N or CR ₉ ego,

X ₂ is selected from the group consisting of O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ),

Y ₁ to Y ₈ And are each the same or different, are each independently N or CR _10, each R ₁₀ may be the same or different,

R ₁ to R ₁₀ are the same or different and each independently represents hydrogen, 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 , C ₆ ~ C ₄₀ aryl phosphine group, is selected from the group consisting of C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ with an aryl silyl group of C ₄₀ in, which combine groups which are adjacent to form a condensed ring In addition,

Ar ₁ to Ar ₅ are the same or different and each independently represents 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, 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 is selected from the pingi, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ of the group consisting of aryl silyl,

R ₁ to R ₁₀ And Ar ₁ to Ar _{5 each} independently represent 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 An arylphosphine oxide group and an arylsilyl group of C ₆ to C ₄₀ are each independently selected from the group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, 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, a C ₆ to C ₄₀ arylamine group , C ₃ ~ C ₄₀ cycloalkyl group, a 3 to 40 nuclear atoms of a heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl , C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and aryl of C ₆ ~ C ₄₀ And a silyl group. When there are a plurality of substituents, they may be the same or different.

Also, the present invention is an organic electroluminescent device comprising a cathode, 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 of the above formula And an organic electroluminescent device.

At least one of the one or more organic layers 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, and is preferably a light emitting layer. At this time, the compound represented by Formula 1 is a blue, green or red phosphorescent host material.

The compound represented by the general formula (1) of the present invention is excellent in thermal stability and phosphorescence properties and can be used as a material for an organic material layer of an organic electroluminescent device. In particular, when the compound represented by Formula 1 of 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 as compared with conventional host materials, And a full color display panel in which the lifetime is greatly improved can also be manufactured.

Hereinafter, the present invention will be described in detail.

<Novel compound>

The novel compound according to the present invention has a basic skeleton formed by fusing an indole moiety to the end of an indolophenanthridine moiety or a benzoimidazolophenanthridine moiety, And has a structure in which various substituents are bonded to a basic skeleton, and is represented by the above formula (1).

The compound represented by Formula 1 has a broad band gap due to an indole moiety bonded to the end of an indolophenanthridine moiety or a benzoimidazolophenanthridine moiety But also various bipolar characteristics of the molecule due to various aromatic ring substituents, thereby enhancing the bonding force between holes and electrons. Therefore, the compound of Formula 1 can improve the phosphorescence characteristic of the organic EL device, and improve the hole injecting ability, transporting ability, or light emitting efficiency.

Further, since the aromatic ring substituent introduced into the indole moiety significantly increases the molecular weight of the compound, the glass transition temperature can be improved, and thus, the conventional CBP (4,4-dicarbazolylbiphenyl) It can have higher thermal stability. In addition, since the chemical is effective in inhibiting the crystallization of the organic material layer, the organic EL device including the compound of Formula 1 according to the present invention can greatly improve durability and lifetime characteristics.

Specifically, when the compound represented by the formula (1) of the present invention is used as a blue, green and / or red phosphorescent host material as a material for a positive hole injection / transport layer of an organic EL device, the efficiency and life Excellent effect can be exhibited. Therefore, the compound represented by the general formula (1) of the present invention can greatly contribute to improvement of the performance and lifetime of the organic EL device, and the lifetime of the organic EL device can be maximized in the full color organic light emitting panel.

The compound represented by the formula (1) of the present invention in which a condensed ring is formed in combination with the formula (2) may be further represented by a compound represented by any one of the following formulas (3) to (8). The compounds represented by the formulas (3) to (8) are preferable in consideration of the characteristics of the organic EL device.

In the above Formulas 3 to 8,

X ₁ , X _{2 ,} R ₁ to R _8, and Y ₁ to Y ₈ are as defined in Formula 1, respectively.

More particularly, X ₁ is N or CR _9, X ₂ is selected from O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and _{Si (Ar 4) (Ar 5} ) . Preferably, X ₁ is N or CR ₉ and X ₂ is N (Ar ₁ ), more preferably X ₁ is N and X ₂ is N (Ar ₁ ).

Y ₁ to Y ₈ Are the same or different and are each independently N or CR ₁₀ , Wherein each R &lt; ₁₀ &gt; may be the same or different. Preferably, Y ₁ to Y ₈ are both CR _10, wherein each R ₁₀ may be the same or different.

Also, Ar ₁ to Ar ₅ Are each independently of the other C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₆ to C ₄₀ aryl, and 5 to 40 heteroaryl group, C ₆ ~ aryloxy C ₄₀ of, 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 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl of the 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 ~ It is selected from the group consisting of C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl group in the silyl.

When considering the characteristics of the organic EL device, the above Ar ₁ to Ar ₅ may be the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₄₀ aryl group or a substituted or unsubstituted nuclear atom More preferably 5 to 40 heteroaryl groups.

R ₁ to R ₁₀ excluding at least one of R ₁ and R ₂ , R ₂ and R ₃ , and / or R ₃ and R ₄ may be the same as or different from each other, or different, and each independently represent hydrogen, deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ aryl of C ₄₀ alkynyl group, C ₆ ~ C ₄₀ of , 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, An alkyl 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 aryl A phosphine group, an arylphosphine oxide group having ₆ to ₄₀ carbon atoms, and an arylsilyl group having ₆ to ₄₀ carbon atoms, which may be bonded to adjacent groups to form a condensed ring.

In the present invention, each of R ₁ to R ₁₀ independently represents hydrogen, deuterium (D), a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, And a substituted or unsubstituted C ₆ to C ₄₀ arylamine group.

Here, R ₁ to R ₁₀ And Ar ₁ to Ar _{5 each} independently represent an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, 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 alkenyl group, an aryloxycarbonyl group, an aryloxycarbonyl 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, a C ₆ to C ₄₀ aryl An amino 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 aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group may be substituted with at least one member selected from the group consisting of have. When there are a plurality of substituents, the plurality of substituents may be the same as or different from each other.

The compound represented by the formula (1) of the present invention having a condensed ring in combination with the formula (2) is more preferably a compound represented by any one of the following formulas (9) to (20). The compounds represented by the formulas (9) to (20) are more preferable in consideration of the characteristics of the organic EL device.

In the general formulas (9) to (20), R ₁ to R ₈ and Ar ₁ are as defined in the general formula (1).

More specifically, Ar ₁ Are C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₆ of the ~ of aryloxy group of C _40, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₄₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group of, C ₁ ~ C ₄₀ groups of the alkyl silyl group, C ₁ ~ C ₄₀ alkyl, boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C of _And an arylsilyl group having ₆ to ₄₀ carbon atoms.

When considering the characteristics of the organic EL device, it is preferable that Ar ₁ is a substituted or unsubstituted C ₆ -C ₄₀ aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms.

R ₁ to R ₈ excluding at least one of R ₁ and R ₂ , R ₂ and R ₃ , and / or R ₃ and R ₄ are the same as or different from each other, or different, and each independently represent hydrogen, deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ aryl of C ₄₀ alkynyl group, C ₆ ~ C ₄₀ of , 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, An alkyl 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 aryl A phosphine group, an arylphosphine oxide group having ₆ to ₄₀ carbon atoms, and an arylsilyl group having ₆ to ₄₀ carbon atoms, which may be bonded to adjacent groups to form a condensed ring.

In the present invention, R ₁ to R ₈ are each independently hydrogen, deuterium (D), a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms, and it is preferably a substituted or unsubstituted C ₆ ~ selected from the group consisting of C ₄₀ arylamines.

Here, R ₁ to R ₈ And Ar ₁ to Ar _{5 each} independently represent an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, 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 alkenyl group, an aryloxycarbonyl group, an aryloxycarbonyl 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, a C ₆ to C ₄₀ aryl An amino 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 aryl boron group, C ₆ ~ C ₄₀ aryl phosphine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ aryl silyl group may be substituted with at least one member selected from the group consisting of have. When there are a plurality of substituents, the plurality of substituents may be the same as or different from each other.

In the compound of formula (I) according to the present invention, R ₁ to R ₁₀ And Ar ₁ to Ar ₅ are each independently selected from the group consisting of hydrogen or the substituents represented by the following S1 to S204, but are not limited thereto.

More preferably, R ₁ to R ₁₀ and Ar ₁ to Ar ₅ each independently may be selected from hydrogen or the following substituent group.

The compounds of the present invention described above can be further exemplified by the following exemplified structures. However, the compounds represented by formula (1) of the present invention are not limited by the following examples.

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, , Hexyl, and the like.

The "alkenyl" in the present invention is a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl, allyl allyl, isopropenyl, 2-butenyl, and the like.

"Alkynyl" in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include ethynyl, 2-propynyl, and the like.

In the present invention, "aryl" 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 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, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, 2-furanyl, N-imidazolyl, 2- isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like.

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 phenyloxy, naphthyloxy, diphenyloxy and the like.

The term "alkyloxy" in the present invention 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 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 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 carbon, preferably 1 to 3 carbons, of the ring is replaced by N, O, S or Se. &Lt; / RTI &gt; Examples of such heterocycloalkyl include morpholine, piperazine and the like.

"Alkylsilyl" in the present invention means a 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 &

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising the compound represented by Formula 1 according to the present invention.

Specifically, the organic electroluminescent device of the present invention includes an anode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, A compound represented by the formula (1), preferably a compound represented by the formula (3) to (8). At this time, the compound of formula (1) 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. [ At this time, it is preferable that the organic material layer including the compound of Formula 1 is a light emitting layer.

Specifically, the light emitting layer of the organic electroluminescent device of the present invention may include a host material, which may include the compound of Formula 1 as a host material. 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 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 represented by the general formula (1) of the present invention can be used as a phosphorescent host material in the light emitting layer. On the other hand, 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 of the organic material layers (for example, the light emitting layer) An organic material 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.

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.

Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), 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.

Examples of the negative electrode material 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  One] IPT Synthesis of -1

<Step 1> Synthesis of 4- (2- nitrophenyl ) -1H- indole Synthesis of

(17.25 g, 88.0 mmol), 2-nitrophenylboronic acid (16.1 g, 96.7 mmol), NaOH (10.6 g, 264.0 mmol) and THF / H ₂ O (1000 ml / 500 ml ) Were added and stirred. At 40 ℃ into the _{Pd (PPh 3) 4 (5.1} g, 5 mol%), and the mixture was stirred at 80 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 4- (2-nitrophenyl) -1H-indole (16.4 g, 68.6 mmol, yield 78%) was obtained by column chromatography.

¹ H-NMR:? 6.52 (d, 1 H), 7.31 (m, 2H), 7.62 (m, 3H)

&Lt; Step 2 > 1- (2- bromophenyl ) -4- (2- nitrophenyl ) -1H- indole Synthesis of

1-bromo-2-iodobenzene (52.6 g, 186.0 mmol), Cu powder (0.40 g, 6.20 mmol), K ₂ CO ₃ (25.7 g, 186.0 mmol) and nitrobenzene (300 ml) were mixed and stirred at 190 ° C for 12 hours.

After the reaction was completed, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain the objective compound 1- (2-bromophenyl) -4- (2-nitrophenyl) -1H-indole (15.8 g, 40.3 mmol, yield 65%).

^{1 H-NMR: δ 6.52 (} d, 1H), 7.35 (m, 2H), 7.61 (m, 5H), 7.93 (m, 4H), 8.07 (d, 1H)

&Lt; Step 3 > 13- (2- nitrophenyl ) indolo [1,2-f] 피탄 히드INE Synthesis of

(13.8 g, 35.0 mmol), cesium fluoride (15.5 g, 105 mmol) and Pd ₂ (dba) ₃ (0.91 g, 105 mmol) were added to a solution of 1- (2-bromophenyl) -4- 0.875 mmol) and dppp (0.7 g, 1.75 mmol) were added to CH ₃ CN (150 ml) and Toluene (150 ml) and stirred. 2- (trimethylsilyl) phenyl trifluoromethanesulfonate (10.4 g, 35.0 mmol) was dissolved in CH ₃ CN (75 ml) and toluene (75 ml), and the mixture was slowly added dropwise. After the reaction was completed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain 13- (2-nitrophenyl) indolo [1,2-f] phenanthridine (7.21 g, 18.6 mmol, yield 53%).

^{1 H-NMR: δ 6.28 (} s, 1H), 7.49 (m, 4H), 7.79 (m, 5H), 7.99 (m, 5H), 8.61 (d, 1H)

<Step 4> IPT - 1 of  synthesis

Dichlorobenzene (50 ml) and triphenylphosphine (9.46 g, 36.1 mmol) were added to the reaction mixture under a nitrogen stream for 12 hours Lt; / RTI &gt; After completion of the reaction, 1,2-dichlorobenzene was removed and extracted with dichloromethane. The extracted organic layer was washed with MgSO ₄ , and IPT-1 (3.95 g, 11.1 mmol, yield 77%) was obtained by column chromatography.

¹ H-NMR:? 6.33 (s, 1 H), 7.36 (m, 4H), 7.54 (m, 4H), 7.76 s, 1 H)

[ Preparation Example  2] IPT -2 and IPT Synthesis of -3

<Step 1> 5- (2- nitrophenyl ) -1H- indole Synthesis of

The procedure of Step 1 of Preparation Example 1 was repeated except that 5-bromo-1H-indole (17.25 g, 88.0 mmol) was used instead of 4-bromo-1H- indole to obtain 5- (2-nitrophenyl) -1H-indole (15.7 g, 66.0 mmol, yield 75%).

¹ H-NMR:? 6.45 (d, IH), 7.28 (d, IH), 7.68 (m, 3H)

&Lt; Step 2 > 1- (2- bromophenyl ) -5- (2- nitrophenyl ) -1H- indole Synthesis of

Step 2 of Preparation Example 1 was repeated except that 5- (2-nitrophenyl) -1H-indole (14.8 g, 62.0 mmol) was used instead of 4- (2-nitrophenyl) To obtain 1- (2-bromophenyl) -5- (2-nitrophenyl) -1H-indole (16.5 g, 42.2 mmol, yield 68%).

^{1 H-NMR: δ 6.51 (} d, 1H), 7.48 (m, 3H), 7.61 (m, 4H), 7.98 (m, 4H), 8.18 (d, 1H)

<Step 3> Synthesis of 12- (2- nitrophenyl ) indolo [1,2-f] 피탄 히드INE Synthesis of

(2-bromophenyl) -5- (2-nitrophenyl) -1H-indole (13.8 g, 35.0 mmol) was used instead of 1- (2-bromophenyl) -4- (2-nitrophenyl) indolo [1,2-f] phenanthridine (7.48 g, 19.3 mmol, yield 55%) was obtained in the same manner as in <Step 3> of Preparation Example 1,

^{1 H-NMR: δ 6.28 (} s, 1H), 7.48 (m, 2H), 7.64 (m, 6H), 7.98 (m, 6H), 8.61 (d, 1H)

<Step 4> IPT -2 and IPT Synthesis of -3

Except that 12- (2-nitrophenyl) indolo [1,2-f] phenanthridine (5.61 g, 14.4 mmol) was used in place of 13- (2-nitrophenyl) indolo [ (1.90 g, 5.33 mmol, yield 37%) and IPT-3 (1.80 g, 5.19 mmol, yield 36%) were obtained in the same manner as in <Step 4>.

¹ H-NMR of IPT-2:? 6.28 (d, 1H), 7.48 (m, 6H), 7.79 (m, 4H), 8.03 )

Of ^{IPT-3 1 H-NMR:} δ 6.28 (d, 1H), 7.45 (m, 4H), 7.73 (m, 6H), 8.00 (m, 3H), 8.62 (d, 1H), 10.09 (s, 1H )

[ Preparation Example  3] IPT -4 and IPT Synthesis of -5

&Lt; Step 1 > 6- (2- nitrophenyl ) -1H- indole Synthesis of

The procedure of Step 1 of Preparation Example 1 was repeated except that 6-bromo-1H-indole (17.25 g, 88.0 mmol) was used instead of 4-bromo-1H- indole to obtain 6- (2-nitrophenyl) -1H-indole (14.9 g, 62.5 mmol, yield 71%).

¹ H-NMR:? 6.45 (d, IH), 7.27 (d, IH), 7.69 (m, 3H), 7.99

&Lt; Step 2 > 1- (2- bromophenyl ) -6- (2- nitrophenyl ) -1H- indole Synthesis of

Step 2 of Preparation Example 1 was repeated except that 6- (2-nitrophenyl) -1H-indole (14.8 g, 62.0 mmol) was used instead of 4- (2-nitrophenyl) To obtain 1- (2-bromophenyl) -6- (2-nitrophenyl) -1H-indole (15.3 g, 39.1 mmol, yield 63%).

^{1 H-NMR: δ 6.50 (} d, 1H), 7.33 (t, 1H), 7.56 (m, 6H), 7.98 (m, 3H), 8.44 (d, 1H)

<Step 3> Synthesis of 11- (2- nitrophenyl ) indolo [1,2-f] 피탄 히드INE Synthesis of

(2-bromophenyl) -6- (2-nitrophenyl) -1H-indole (13.8 g, 35.0 mmol) was used instead of 1- (2-bromophenyl) -4- (2-nitrophenyl) indolo [1,2-f] phenanthridine (7.48 g, 19.3 mmol, yield 55%) was obtained in the same manner as in <Step 3> of Preparation Example 1,

^{1 H-NMR: δ 6.28 (} d, 1H), 7.43 (m, 2H), 7.68 (m, 6H), 7.98 (m, 4H), 8.16 (d, 1H), 8.63 (d, 1H), 10.12 ( d, 1 H)

<Step 4> IPT -4 and IPT Synthesis of -5

Except that 11- (2-nitrophenyl) indolo [1,2-f] phenanthridine (5.61 g, 14.4 mmol) was used in place of 13- (2-nitrophenyl) indolo [ (1.80 g, 5.19 mmol, yield 36%) and IPT-5 (1.95 g, 5.62 mmol, yield 39%) were obtained in the same manner as in <Step 4> of <Step 4>.

The ^{IPT-4 1 H-NMR:} δ 6.28 (d, 1H), 7.43 (m, 5H), 7.73 (m, 4H), 8.00 (m, 2H), 8.11 (m, 2H), 8.61 (d, 1H ), 10.08 (s, 1 H)

The ^{IPT-5 1 H-NMR:} δ 6.28 (d, 1H), 7.49 (m, 6H), 7.70 (m, 4H), 8.02 (m, 2H), 8.12 (d, 1H), 8.62 (d, 1H ), 10.09 (s, 1 H)

[ Preparation Example  4] IPT Synthesis of -6

&Lt; Step 1 > 7- (2- nitrophenyl ) -1H- indole Synthesis of

(2-nitrophenyl) indole was prepared by following the procedure of Step 1 of Preparation Example 1, except that 7-bromo-1H-indole (17.25 g, 88.0 mmol) was used instead of 4-bromo- -1H-indole (16.5 g, 69.5 mmol, yield 79%).

¹ H-NMR:? 6.45 (d, 1 H), 7.31 (m, 2H), 7.69

&Lt; Step 2 > 1- (2- bromophenyl ) -7- (2- nitrophenyl ) -1H- indole Synthesis of

The same procedure as in <Step 2> of Preparation Example 1 was carried out except that 7- (2-nitrophenyl) -1H-indole (14.8 g, 62.0 mmol) was used instead of 4- (2-nitrophenyl) To obtain 1- (2-bromophenyl) -7- (2-nitrophenyl) -1H-indole (16.5 g, 42.2 mmol, yield 68%).

^{1 H-NMR: δ 6.51 (} d, 1H), 7.31 (m, 2H), 7.51 (m, 2H), 7.61 (m, 3H), 7.98 (m, 4H), 8.28 (d, 1H)

<Step 3> Synthesis of 10- (2- nitrophenyl ) indolo [1,2-f] 피탄 히드INE Synthesis of

1- (2-bromophenyl) -7- (2-nitrophenyl) -1H-indole (13.8 g, 35.0 mmol) was used instead of 1- (2-bromophenyl) -4- (2-nitrophenyl) indolo [1,2-f] phenanthridine (8.02 g, 20.7 mmol, yield 59%) was obtained in the same manner as <Step 3> of Preparation Example 1,

^{1 H-NMR: δ 6.28 (} d, 1H), 7.44 (m, 3H), 7.61 (m, 2H), 7.71 (m, 2H), 7.98 (m, 7H), 8.58 (d, 1H)

<Step 4> IPT Synthesis of -6

Except that 10- (2-nitrophenyl) indolo [1,2-f] phenanthridine (5.61 g, 14.4 mmol) was used in place of 13- (2-nitrophenyl) indolo [ Of the objective compound IPT-6 (3.65 g, 10.2 mmol, yield 71%) was obtained in the same manner as in <Step 4>.

^{1 H-NMR: δ 6.31 (} d, 1H), 7.31 (m, 2H), 7.55 (m, 5H), 7.78 (m, 2H), 7.99 (m, 4H), 8.60 (d, 1H), 10.09 ( s, 1 H)

[ Preparation Example  5] IPT - 7 and IPT Synthesis of -8

<Step 1> Synthesis of N- (2,5- 디브롬ophenyl ) phenanthridin -6- amine Synthesis of

6-chlorophenanthridine (18.8 g, 88.0 mmol), 2,5-dibromoaniline (24.3 g, 96.7 mmol) and 1000 ml of diglyme were added under nitrogen flow and the mixture was stirred at 160 ° C for 3 hours. After completion of the reaction, the mixture was filtered and recrystallized from EA and hexane to obtain the target compound, N- (2,5-dibromophenyl) phenanthridin-6-amine (29.4 g, 68.6 mmol, yield 78%).

^{1 H-NMR: δ 4.12 (} s, 1H), 6.78 (m, 2H), 7.21 (d, 1H), 7.35 (m, 3H), 7.71 (m, 3H), 7.92 (d, 1H), 8.12 ( d, 1 H)

<Step 2> IPTN - Br  synthesis

(37.2 g, 87.0 mmol), triphenylphosphine (4.5 g, 17 mmol), palladium acetate (1.2 g, 5 mmol), pstassium carbonate (36.0 g, 260 mmol) mmol) were added to 1000 ml of toluene and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, IPTN-Br (19.0 g, 54.8 mmol, yield 63%) was obtained by column chromatography.

^{1 H-NMR: δ 7.41 (} m, 4H), 7.65 (t, 1H), 7.79 (m, 3H), 7.99 (m, 2H), 8.62 (d, 1H)

<Step 3> IPTN1 Synthesis of

IPTNl (24.3 g, 62.5 mmol, yield 71%) was prepared by the same procedure as <Step 1> of Preparation Example 1 except that IPTN-Br (30.6 g, 88.0 mmol) was used instead of 4-bromo- ).

^{1 H-NMR: δ 7.47 (} m, 2H), 7.69 (m, 2H), 7.78 (m, 2H), 7.99 (m, 6H), 8.28 (d, 1H), 8.62 (d, 1H)

<Step 4> IPT -7 and IPT Synthesis of -8

Step 4 of Preparation Example 1 was repeated except that IPTN1 (5.61 g, 14.4 mmol) was used in place of 13- (2-nitrophenyl) indolo [1,2-f] phenanthridine to obtain the desired compound IPT- 7 (1.80 g, 5.19 mmol, yield 36%) and IPT-8 (1.65 g, 4.76 mmol, yield 33%).

The ^{IPT-7 1 H-NMR:} δ 7.31 (t, 1H), 7.47 (m, 3H), 7.73 (m, 6H), 8.00 (m, 2H), 8.11 (d, 1H), 8.61 (d, 1H ), 10.07 (s, 1 H)

The ^{IPT-8 1 H-NMR:} δ 7.30 (t, 1H), 7.49 (m, 3H), 7.72 (m, 4H), 7.88 (d, 1H), 8.02 (m, 2H), 8.18 (m, 2H ), 8.62 (d, 1 H), 10.09 (s, 1 H)

[ Preparation Example  6] IPT -9 and IPT Synthesis of -10

<Step 1> 5- (5- chloro -2- nitrophenyl ) -1H- indole Synthesis of

5-chloro-2-nitrophenylboronic acid (19.47 g, 96.7 mmol) was used instead of 2-nitrophenylboronic acid in Step 2 of Preparation Example 2, nitrophenyl) -1H-indole (17.0 g, 62.5 mmol, yield 71%).

¹ H-NMR:? 6.45 (d, IH), 7.27 (d, IH), 7.63 (m, 3H), 7.95

&Lt; Step 2 > 1- (2- bromophenyl ) -5- (5- chloro -2- nitrophenyl ) -1H- indole Synthesis of

Step 2 of Preparation Example 1 was repeated except that 5- (5-chloro-2-nitrophenyl) -1H-indole (16.9 g, 62.0 mmol) was used instead of 4- (2-nitrophenyl) The same procedure was followed to obtain 1- (2-bromophenyl) -5- (5-chloro-2-nitrophenyl) -1H-indole (18.1 g, 42.2 mmol, yield 68%).

^{1 H-NMR: δ 6.50 (} d, 1H), 7.31 (t, 1H), 7.54 (m, 5H), 7.99 (m, 3H), 8.44 (d, 1H)

<Step 3> Synthesis of 12- (5- chloro -2- nitrophenyl ) indolo [1,2-f] 피탄 히드INE Synthesis of

5- (5-chloro-2-nitrophenyl) -1H-indole (15.0 g, 35.0 mmol) was used instead of 1- (2-bromophenyl) -4- (2-nitrophenyl) 2-nitrophenyl) indolo [1,2-f] phenanthridine (8.61 g, 20.4 mmol, yield 58%) was obtained by following the procedure of <Step 3> of Preparation Example 1, %).

^{1 H-NMR: δ 6.25 (} d, 1H), 7.47 (m, 2H), 7.64 (m, 5H), 7.99 (m, 4H), 8.16 (d, 1H), 8.68 (d, 1H), 10.12 ( d, 1 H)

<Step 4> IPT -9 and IPT Synthesis of -10

Except that 12- (5-chloro-2-nitrophenyl) indolo [1,2-f] phenanthridine (6.09 g, 14.4 mmol) was used in place of 13- (2-nitrophenyl) indolo [ (1.80 g, 4.61 mmol, yield 32%) and IPT-10 (2.19 g, 5.62 mmol, yield 39%) were obtained in the same manner as in <Step 4> of Preparation Example 1.

The ^{IPT-9 1 H-NMR:} δ 6.28 (d, 1H), 7.46 (m, 5H), 7.71 (m, 3H), 8.01 (m, 2H), 8.11 (m, 2H), 8.63 (d, 1H ), 10.12 (s, 1 H)

The ^{IPT-10 1 H-NMR:} δ 6.29 (d, 1H), 7.43 (m, 6H), 7.75 (m, 3H), 8.04 (m, 2H), 8.12 (d, 1H), 8.62 (d, 1H ), 10.10 (s, 1 H)

[ Synthetic example  1] Synthesis of C 1

IPT-1 (3.56 g, 10.00 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.67 g, 10.00 mmol), NaH (0.24 g, 10.00 mmol) and DMF 50 ml) were mixed and stirred at room temperature for 1 hour. After completion of the reaction, water was added thereto, and the solid compound was filtered, and then purified by column chromatography to obtain the target compound C 1 (5.47 g, yield 93%).

GC-Mass (calculated: 587.67 g / mol, measured: 587 g / mol)

[ Synthetic example  2] Synthesis of C 2

The same procedure as in Synthesis Example 1 was carried out except that 2-chloro-4,6-diphenylpyrimidine (2.67 g, 10.00 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5- To obtain the target compound C 2 (4.99 g, yield 85%).

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[ Synthetic example  3] Synthesis of C 17

IPF-1 (3.56 g, 10.00 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (4.66 g, 12.00 mmol) and Cu powder (0.06 g _{in, 1.00 mmol), K 2 CO} 3 (2.76 g, 20.00 mmol), Na 2 SO 4 (2.84 g, 20.00 mmol) , and nitrobenzene (200 ℃ mixed and a 50 ml) was stirred for 12 hours.

After the reaction was completed, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removal of the organic layer solvent, the residue was purified by column chromatography to give the desired compound C17 (4.91 g, yield 74%).

GC-Mass (calculated: 663.77 g / mol, measured: 663 g / mol)

[ Synthetic example  4] Synthesis of C 19

Except that 2- (3-bromophenyl) -4,6-diphenylpyridine (4.63 g, 12.00 mmol) was used instead of 2- (3-bromophenyl) -4,6- diphenyl- The procedure of Example 3 was repeated to obtain the target compound C19 (4.17 g, yield 63%).

GC-Mass (theory: 661.79 g / mol, measured: 661 g / mol)

[ Synthetic example  5] Synthesis of C 25

(3'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3-bromophenyl) -4,6-diphenyl- g, 12.00 mmol), the target compound C 25 (4.17 g, yield 63%) was obtained.

GC-Mass (739.86 g / mol, measured: 739 g / mol)

[ Synthetic example  6] Synthesis of C 27

2- (4'-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3-bromophenyl) -4,6- diphenyl- g, 12.00 mmol), the target compound C 27 (4.57 g, yield 69%) was obtained.

GC-Mass (739.86 g / mol, measured: 739 g / mol)

[ Synthetic example  7] Synthesis of C 57

The procedure of Synthesis Example 1 was repeated except that IPT-2 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the target compound C 57 (5.52 g, yield 94%).

GC-Mass (calculated: 587.67 g / mol, measured: 587 g / mol)

[ Synthetic example  8] Synthesis of C 58

The procedure of Synthesis Example 2 was repeated except that IPT-2 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain C 58 (5.28 g, yield 90%) as a target compound.

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[ Synthetic example  9] Synthesis of C 73

The procedure of Synthetic Example 3 was repeated except that IPT-2 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the target compound C73 (4.91 g, yield 74%).

GC-Mass (calculated: 663.77 g / mol, measured: 663 g / mol)

[ Synthetic example  10] Synthesis of C 75

The procedure of Synthetic Example 4 was repeated except that IPT-2 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the target compound C 75 (4.57 g, yield 69%).

GC-Mass (theory: 661.79 g / mol, measured: 661 g / mol)

[ Synthetic example  11] Synthesis of C 81

The procedure of Synthetic Example 5 was repeated except that IPT-2 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the desired compound C 81 (4.57 g, yield 63%).

GC-Mass (739.86 g / mol, measured: 739 g / mol)

[ Synthetic example  12] Synthesis of C 83

The procedure of Synthetic Example 6 was repeated except that IPT-2 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the target compound C83 (4.96 g, yield 67%).

GC-Mass (739.86 g / mol, measured: 739 g / mol)

[ Synthetic example  13] Synthesis of C 113

The procedure of Synthesis Example 1 was repeated except that IPT-3 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the target compound C 113 (5.35 g, yield 91%).

GC-Mass (calculated: 587.67 g / mol, measured: 587 g / mol)

[ Synthetic example  14] Synthesis of C 114

The procedure of Synthesis Example 2 was repeated except that IPT-3 (3.56 g, 10.00 mmol) was used in place of IPT-1 to obtain C 114 (5.28 g, yield 90%) as a target compound.

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[ Synthetic example  15] Synthesis of C 129

The procedure of Synthesis Example 3 was repeated except that IPT-3 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the desired compound C 129 (5.11 g, yield 77%).

GC-Mass (calculated: 663.77 g / mol, measured: 663 g / mol)

[ Synthetic example  16] Synthesis of C 131

The procedure of Synthesis Example 4 was repeated except that IPT-3 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the desired compound C 131 (4.70 g, yield 71%).

GC-Mass (theory: 661.79 g / mol, measured: 661 g / mol)

[ Synthetic example  17] Synthesis of C 137

The procedure of Synthetic Example 5 was repeated except that IPT-3 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the desired compound C 137 (5.03 g, yield 68%).

GC-Mass (739.86 g / mol, measured: 739 g / mol)

[ Synthetic example  18] Synthesis of C 139

The procedure of Synthesis Example 6 was repeated except that IPT-3 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the desired compound C 139 (4.96 g, yield 67%).

GC-Mass (739.86 g / mol, measured: 739 g / mol)

[ Synthetic example  19] Synthesis of C 169

The procedure of Synthesis Example 1 was repeated except that IPT-4 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the desired compound C 169 (5.41 g, yield 92%).

GC-Mass (calculated: 587.67 g / mol, measured: 587 g / mol)

[ Synthetic example  20] Synthesis of C 170

The procedure of Synthesis Example 2 was repeated except that IPT-4 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the target compound C 170 (5.28 g, yield 90%).

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[ Synthetic example  21] Synthesis of C 185

The procedure of Synthesis Example 3 was repeated, except that IPT-4 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the desired compound C 185 (4.71 g, yield 71%).

GC-Mass (calculated: 663.77 g / mol, measured: 663 g / mol)

[ Synthetic example  22] Synthesis of C 187

The procedure of Synthetic Example 4 was repeated except that IPT-4 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain C187 (4.50 g, yield 68%) as a target compound.

GC-Mass (theory: 661.79 g / mol, measured: 661 g / mol)

[ Synthetic example  23] Synthesis of C 193

The procedure of Synthetic Example 5 was repeated except that IPT-4 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain C 193 (5.03 g, yield 68%) as a target compound.

GC-Mass (739.86 g / mol, measured: 739 g / mol)

[ Synthetic example  24] Synthesis of C 195

The procedure of Synthetic Example 6 was repeated except that IPT-4 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the desired compound C 195 (4.37 g, yield 59%).

GC-Mass (739.86 g / mol, measured: 739 g / mol)

[ Synthetic example  25] Synthesis of C 225

The procedure of Synthesis Example 1 was repeated except that IPT-5 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the target compound C 225 (5.58 g, yield 95%).

GC-Mass (calculated: 587.67 g / mol, measured: 587 g / mol)

[ Synthetic example  26] Synthesis of C 226

The procedure of Synthesis Example 2 was repeated except that IPT-5 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain C 226 (5.46 g, yield 93%) as a target compound.

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[ Synthetic example  27] Synthesis of C 241

The procedure of Synthesis Example 3 was repeated except that IPT-5 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the target compound C 241 (5.24 g, yield 79%).

GC-Mass (calculated: 663.77 g / mol, measured: 663 g / mol)

[ Synthetic example  28] Synthesis of C 243

The procedure of Synthetic Example 4 was repeated except that IPT-5 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the target compound C243 (5.29 g, yield 80%).

GC-Mass (theory: 661.79 g / mol, measured: 661 g / mol)

[ Synthetic example  29] Synthesis of C 249

The procedure of Synthesis Example 5 was repeated except that IPT-5 (3.56 g, 10.00 mmol) was used in place of IPT-1 to obtain C 249 (5.40 g, yield 73%) as a target compound.

GC-Mass (739.86 g / mol, measured: 739 g / mol)

[ Synthetic example  30] Synthesis of C 251

The procedure of Synthetic Example 6 was repeated except that IPT-5 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the desired compound C 251 (4.96 g, yield 67%).

GC-Mass (739.86 g / mol, measured: 739 g / mol)

[ Synthetic example  31] Synthesis of C 281

The procedure of Synthesis Example 1 was repeated except that IPT-6 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the target compound C281 (5.35 g, yield 91%).

GC-Mass (calculated: 587.67 g / mol, measured: 587 g / mol)

[ Synthetic example  32] Synthesis of C282

The procedure of Synthesis Example 2 was repeated except that IPT-6 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the target compound C282 (5.46 g, yield 93%).

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[ Synthetic example  33] Synthesis of C 297

The procedure of Synthesis Example 3 was repeated except that IPT-6 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the desired compound C 297 (4.91 g, yield 74%).

GC-Mass (calculated: 663.77 g / mol, measured: 663 g / mol)

[ Synthetic example  34] Synthesis of C 299

The procedure of Synthetic Example 4 was repeated except that IPT-6 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the desired compound C 299 (5.36 g, yield 81%).

GC-Mass (theory: 661.79 g / mol, measured: 661 g / mol)

[ Synthetic example  35] Synthesis of C 305

The procedure of Synthesis Example 5 was repeated except that IPT-6 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the target compound C 305 (5.70 g, yield 77%).

GC-Mass (739.86 g / mol, measured: 739 g / mol)

[ Synthetic example  36] Synthesis of C 307

The procedure of Synthesis Example 6 was repeated except that IPT-6 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain C 307 (4.96 g, yield 67%) as a target compound.

GC-Mass (739.86 g / mol, measured: 739 g / mol)

[ Synthetic example  37] Synthesis of C 337

The procedure of Synthesis Example 1 was repeated except that IPT-7 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the target compound C337 (5.35 g, yield 91%).

GC-Mass (calculated: 587.67 g / mol, measured: 587 g / mol)

[ Synthetic example  38] Synthesis of C 338

The procedure of Synthesis Example 2 was repeated except that IPT-7 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain C338 (5.28 g, yield 90%) as a target compound.

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[ Synthetic example  39] Synthesis of C 353

The procedure of Synthesis Example 3 was repeated except that IPT-7 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain C 353 (4.91 g, yield 74%) as a target compound.

GC-Mass (calculated: 663.77 g / mol, measured: 663 g / mol)

[ Synthetic example  40] Synthesis of C 355

The procedure of Synthetic Example 4 was repeated except that IPT-7 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the desired compound C 355 (4.65 g, yield 76%).

GC-Mass (theory: 661.79 g / mol, measured: 661 g / mol)

[ Synthetic example  41] Synthesis of C 361

The procedure of Synthetic Example 5 was repeated except that IPT-7 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the desired compound C361 (5.70 g, yield 77%).

GC-Mass (739.86 g / mol, measured: 739 g / mol)

[ Synthetic example  42] Synthesis of C 363

The procedure of Synthesis Example 6 was repeated except that IPT-7 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the target compound C363 (5.25 g, yield 71%).

GC-Mass (739.86 g / mol, measured: 739 g / mol)

[ Synthetic example  43] Synthesis of C 393

The procedure of Synthesis Example 1 was repeated except that IPT-8 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the target compound C 393 (5.35 g, yield 91%).

GC-Mass (calculated: 587.67 g / mol, measured: 587 g / mol)

[ Synthetic example  44] Synthesis of C 394

The procedure of Synthesis Example 2 was repeated except that IPT-8 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the target compound C 394 (5.46 g, yield 93%).

GC-Mass (calculated: 586.68 g / mol, measured: 586 g / mol)

[ Synthetic example  45] Synthesis of C 409

The procedure of Synthesis Example 3 was repeated except that IPT-8 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the objective compound C 409 (4.65 g, yield 70%).

GC-Mass (calculated: 663.77 g / mol, measured: 663 g / mol)

[ Synthetic example  46] Synthesis of C 411

The procedure of Synthesis Example 4 was repeated except that IPT-8 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the target compound C 411 (4.65 g, yield 76%).

GC-Mass (theory: 661.79 g / mol, measured: 661 g / mol)

[ Synthetic example  47] Synthesis of C 417

The procedure of Synthetic Example 5 was followed except that IPT-8 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the desired compound C 417 (5.33 g, yield 72%).

GC-Mass (739.86 g / mol, measured: 739 g / mol)

[ Synthetic example  48] Synthesis of C 419

The procedure of Synthetic Example 6 was repeated except that IPT-8 (3.56 g, 10.00 mmol) was used instead of IPT-1 to obtain the desired compound C 419 (5.40 g, yield 73%).

GC-Mass (739.86 g / mol, measured: 739 g / mol)

[ Synthetic example  49] Synthesis of C 162

The same procedure as in Synthesis Example 15 was carried out except that (3-bromophenyl) triphenylsilane (4.98 g, 12.00 mmol) was used instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5- To obtain the target compound C 162 (4.21 g, yield 61%).

GC-Mass (calculated: 690.90 g / mol, measured: 690 g / mol)

[ Synthetic example  50] Synthesis of C 167

2- (4-bromophenyl) -5-phenyl-1,3,4-oxadiazole (3.61 g, 12.00 mmol) was used instead of 2- (3-bromophenyl) -4,6-diphenyl- , The target compound C 167 (3.75 g, yield 65%) was obtained by carrying out the same procedure as in Synthesis Example 15.

GC-Mass (calculated: 576.64 g / mol, measured: 576 g / mol)

[ Synthetic example  51] Synthesis of C 168

4- (4-bromophenyl) -3,5-diphenyl-4H-1,2,4-triazole (4.52 g, 12.00) instead of 2- (3-bromophenyl) mmol), the target compound C 168 (4.50 g, yield 69%) was obtained by carrying out the same procedure as in Synthesis Example 15.

GC-Mass (calculated: 651.76 g / mol, measured: 651 g / mol)

[ Synthetic example  52] Synthesis of C 458

2-chloro-4- (3- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) pyrimidine instead of 2- (3-bromophenyl) 4.59 g, 12.00 mmol), the target compound C 458 (5.69 g, yield 81%) was obtained by carrying out the same procedure as in Synthesis Example 15.

GC-Mass (calculated: 702.84 g / mol, measured: 702 g / mol)

[ Synthetic example  53] Synthesis of C 477

Was obtained in the same manner as in Synthesis Example 15, except that 3-bromo-N, N-diphenylaniline (4.59 g, 12.00 mmol) was used instead of 2- (3-bromophenyl) -4,6-diphenyl- To obtain the target compound C 477 (3.90 g, yield 65%).

GC-Mass (calculated: 599.72 g / mol, measured: 599 g / mol)

[ Synthetic example  54] Synthesis of C 480

The same procedure as in Synthesis Example 15 was carried out except that (3-bromophenyl) diphenylphosphineoxide (4.29 g, 12.00 mmol) was used instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5- To obtain the target compound C 480 (3.73 g, yield 59%).

GC-Mass (calculated: 632.69 g / mol, measured: 632 g / mol)

[ Synthetic example  55] Synthesis of C 483

2-chloro-4,6-dip-tolyl-1,3,5-triazine (3.55 g, 12.00 mmol) was used instead of 2- (3-bromophenyl) -4,6-diphenyl- , The target compound C 483 (3.76 g, yield 61%) was obtained by carrying out the same procedure as in Synthesis Example 15.

GC-Mass (calculated: 615.72 g / mol, measured: 615 g / mol)

[ Synthetic example  56] Synthesis of C 479

IPT-3 (3.56 g, 10.00 mmol), triethylamine (1.21 g, 12.00 mmol), chlorodiphenylborane (2.41 g, 12.00 mmol) and Toluene (50 ml) were mixed under nitrogen atmosphere and stirred at 110 ° C for 6 hours. After the reaction was completed, the toluene was removed, the organic layer was separated with methylene chloride, and then the water was removed using MgSO ₄ . After removing the solvent of the organic layer, the residue was purified by column chromatography to obtain the target compound C 479 (2.29 g, yield 44%).

GC-Mass (calculated: 520.43 g / mol, measured: 520 g / mol)

[ Synthetic example  57] Synthesis of C 493

The same procedure as in Synthesis Example 15 was carried out except that 2-chloro-4-phenylquinazoline (2.89 g, 12.00 mmol) was used instead of 2- (3-bromophenyl) -4,6-diphenyl- To obtain the target compound C 493 (3.25 g, yield 58%).

GC-Mass (calculated: 560.65 g / mol, measured: 560 g / mol)

[ Synthetic example  58] Synthesis of C 496

2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.40 g, 12.00 mmol) was used instead of 2- (3-bromophenyl) -4,6-diphenyl- , The target compound C 496 (3.71 g, yield 54%) was obtained by carrying out the same procedure as in Synthesis Example 15.

GC-Mass (686.80 g / mol, measured: 686 g / mol)

[ Synthetic example  59] Synthesis of C 498

4- (biphenyl-4-yl) -2- (4-chlorophenyl) quinazoline (4.71 g, 12.00 mmol) was used instead of 2- (3-bromophenyl) -4,6- diphenyl- , The target compound C 498 (4.21 g, yield 59%) was obtained by carrying out the same procedure as in Synthesis Example 15.

GC-Mass (calculated: 712.84 g / mol, measured: 712 g / mol)

[ Synthetic example  60] Synthesis of C 509

IPT-9-1 (5.38 g, yield 77%) was obtained in the same manner as in Synthesis Example 3, except that IPT-9 (3.91 g, 10.00 mmol) was used instead of IPT-1.

A solution of 5.38 g (7.70 mmol) of 4-bromo-1H-indole, 1.18 g (9.67 mmol) of phenylboronic acid and 1.06 g (26.4 mmol) of NaOH in 100 ml / 50 ml of THF / H₂O was added and stirred. 0.51 g (5 mol%) of Pd (PPh₃)₄And the mixture was stirred at 80 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride,₄And filtered. The solvent of the filtered organic layer was removed, and the desired compound C 509 (4.73 g, 6.39 mmol, yield 83%) was obtained by column chromatography.

GC-Mass (739.86 g / mol, measured: 739 g / mol)

[ Synthetic example  61] Synthesis of C 513

3-ylboronic acid (2.78 g, 9.67 mmol) was used in the place of phenylboronic acid instead of 9-phenyl-9H-carbazol-3- %).

GC-Mass (calculated: 905.05 g / mol, measured: 904 g / mol)

[ Synthetic example  62] Synthesis of C 515

IPT-9-1 (5.38 g, yield 77%) was obtained in the same manner as in Synthesis Example 3, except that IPT-9 (3.91 g, 10.00 mmol) was used instead of IPT-1.

Pd (dba) ₂ (0.22 g, 0.4 mmol) and (t-Bu) ₃ P (0.12 g, 0.25 mmol) were added to a solution of 6.98 g (10.00 mmol) 4-bromo- , 0.6 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, C 515 (6.73 g, 8.1 mmol, yield 81%) was obtained by column chromatography.

GC-Mass (calculated: 830.97 g / mol, measured: 830 g / mol)

[ Synthetic example  63] Synthesis of C 525

Except that IPT-10 (3.91 g, 10.00 mmol) was used instead of IPT-9 and dibenzo [b, d] thiophen-4-ylboronic acid (2.21 g, 9.67 mmol) was used instead of phenylboronic acid. The target compound C 525 (4.31 g, overall yield 51%) was obtained.

GC-Mass (calculated: 846.01 g / mol, measured: 845 g / mol)

[ Synthetic example  64] Synthesis of C 527

The procedure of Synthesis Example 62 was repeated except that IPT-10 (3.91 g, 10.00 mmol) was used instead of IPT-9 and diphenylborane (3.49 g, 21.0 mmol) was used instead of diphenylamine to obtain the target compound C 527 4.55 g, overall yield 55%).

GC-Mass (theory: 827.78 g / mol, measurement: 827 g / mol)

[ Example  1 ~ 61] Green organic EL  Device fabrication

Compounds C 1 to C 527 synthesized in Synthesis Examples 1 to 56 and 60 to 64 were subjected to high purity sublimation purification by a conventionally known method and then a green organic EL device was fabricated according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

(60 nm) / TCTA (80 nm) / each compound of C 1 to C 527 + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ 30 nm) / LiF (1 nm) / Al (200 nm) in this order to form an organic EL device.

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

[ Comparative Example  1] Green organic EL  Device fabrication

A green organic EL device was fabricated in the same manner as in Example 1, except that CBP was used instead of the compound C 1 as a luminescent host material in forming the light emitting layer.

[ Evaluation example  One]

The driving voltage, the current efficiency, and the light emission peak at the current density of 10 mA / cm 2 were measured for each of the green organic EL devices manufactured in Examples 1 to 61 and Comparative Example 1, and the results are shown in Table 1 below.

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 C 1 6.74 515 40.0 Example 2 C 2 6.46 518 41.8 Example 3 C 17 6.71 517 44.2 Example 4 C 19 6.79 515 41.7 Example 5 C 25 6.55 518 41.5 Example 6 C 27 6.69 515 42.7 Example 7 C 57 6.69 518 43.0 Example 8 C 58 6.70 517 43.3 Example 9 C 73 6.34 515 44.1 Example 10 C 75 6.70 518 41.4 Example 11 C 81 6.66 517 42.2 Example 12 C 83 6.65 518 43.1 Example 13 C 113 6.65 515 41.1 Example 14 C 114 6.71 518 42.0 Example 15 C 129 6.72 515 42.5 Example 16 C 131 6.72 518 41.3 Example 17 C 137 6.75 518 41.9 Example 18 C 139 6.73 517 41.6 Example 19 C 169 6.73 517 41.5 Example 20 C 170 6.48 517 41.4 Example 21 C 185 6.86 517 41.2 Example 22 C 187 6.61 518 41.1 Example 23 C 193 6.51 517 42.5 Example 24 C 195 6.77 515 43.1 Example 25 C 225 6.66 518 39.2 Example 26 C 226 6.65 518 41.3 Example 27 C 241 6.65 517 39.7 Example 28 C 243 6.64 515 38.9 Example 29 C 249 6.64 518 41.3 Example 30 C 251 6.63 518 41.3 Example 31 C 281 6.63 518 41.3 Example 32 C 282 6.62 518 41.2 Example 33 C 297 6.62 518 41.2 Example 34 C 299 6.62 517 42.9 Example 35 C 305 6.48 515 39.6 Example 36 C 307 6.86 518 40.4 Example 37 C 337 6.61 518 40.1 Example 38 C 338 6.70 517 40.8 Example 39 C 353 6.73 518 40.7 Example 40 C 355 6.75 518 40.5 Example 41 C 361 6.77 517 40.4 Example 42 C 363 6.76 515 41.7 Example 43 C 393 6.72 518 41.5 Example 44 C 394 6.70 515 42.7 Example 45 C 409 6.66 518 42.7 Example 46 C 411 6.81 518 43.1 Example 47 C 417 6.66 518 43.5 Example 48 C 419 6.81 518 41.4 Example 49 C 162 6.68 517 42.2 Example 50 C 167 6.66 517 42.0 Example 51 C 168 6.70 515 41.8 Example 52 C 458 6.70 518 42.0 Example 53 C 477 6.51 518 42.5 Example 54 C 480 6.77 517 41.3 Example 55 C 483 6.46 515 41.3 Example 56 C 479 6.71 518 41.6 Example 57 C 509 6.72 518 41.5 Example 58 C 513 6.70 515 42.7 Example 59 C 515 6.51 518 42.5 Example 60 C 525 6.70 518 42.0 Example 61 C 527 6.70 517 40.8 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, the green organic EL devices (Examples 1 to 61) using the compound (C 1 to C 527) according to the present invention as a light emitting layer were the green organic EL devices (Comparative Example 1) It can be seen that it shows superior performance in terms of efficiency and driving voltage.

[ Example  62 ~ 65] Red organic EL  Device fabrication

Compounds C 129, C 493, C 496 and C 498 synthesized in Synthesis Examples 15 and 57 to 59 were subjected to high purity sublimation purification by a conventionally known method and then red organic electroluminescent devices were fabricated according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

(60 nm) / TCTA (80 nm) / each of compounds C 129, C 493, C 496 and C 498 + 10% (piq) ₂ Ir (acac) (300 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[ Comparative Example  2] Red organic EL  Device fabrication

A red organic electroluminescent device was fabricated in the same manner as in Example 62, except that CBP was used in place of the compound C 129 as a luminescent host material in forming the light emitting layer.

The structures of m-MTDATA, (piq) ₂ Ir (acac), CBP and BCP used in Examples 62 to 65 and Comparative Example 2 are as follows.

[ Evaluation example  2]

The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 62 to 65 and Comparative Example 2, and the results are shown in Table 2 below.

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 62 C 129 4.6 13.3 Example 63 C 493 4.63 12.9 Example 64 C 496 4.6 12.7 Example 65 C 498 4.59 13 Comparative Example 2 CBP 5.25 8.2

As shown in the above Table 2, the red organic electroluminescent devices (Examples 62 to 65) using the compounds (C 129, C 493, C 496 and C 498) according to the present invention as light emitting layers, (Comparative Example 2) as compared with the red organic electroluminescent device used as the red organic electroluminescent device (Comparative Example 2).

Claims (8)

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

In Formula 1,
At least one of R ₁ and R ₂ , R ₂ and R _3, or at least one of R ₃ and R ₄ is bonded to the following formula 2 to form a condensed ring,
(2)

In the formula (2), the dotted line represents a site where condensation is performed with the compound of the formula (1)
X &lt; ₁ &gt; is N or CR &lt; ₉ &
X ₂ is N (Ar ₁ )
Y ₁ to Y ₈ are the same as or different from each other, each independently CR ₁₀ , each R ₁₀ may be the same or different,
R ₁ to R ₁₀ are the same as or different from each other and each independently represents hydrogen, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ arylamine group, and C ₆ To C ₄₀ aryl boron groups, which may be bonded to adjacent groups to form a condensed ring,
Ar ₁ is selected from the group consisting of an aryl boronic of C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, and a C ₆ ~ C ₄₀ of,
Wherein R ₁ to R ₁₀ of C ₆ ~ C ₄₀ aryl group, the number of 5 to 40 heterocyclic nucleus atoms an aryl group, C ₆ ~ C ₄₀ aryl amine group, and a C ₆ ~ aryl of C ₄₀ boron groups, wherein Ar ₁ a C ₆ ~ C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, and a C ₆ ~ C ₄₀ aryl boronic groups are each independently C ₆ ~ C ₄₀ aryl group, a heteroaryl of nuclear atoms of 5 to 40 an aryl group, may be substituted with a C ₆ ~ C ₄₀ aryl amine group, a C ₆ ~ C ₄₀ aryl phosphine oxide groups and at least one member selected from the group consisting of a C ₆ ~ C ₄₀ aryl silyl.
The compound according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (3) to (8).
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In formulas (3) to (8)
X ₁ , X _{2 ,} R ₁ to R ₈ and Y ₁ to Y ₈ are as defined in claim 1, respectively.
The compound according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (9) to (14), (18)
[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 18]

[Chemical Formula 19]

In the above Formulas 9 to 14, 18 and 19,
R ₁ to R ₈ and Ar ₁ are as defined in claim 1, respectively.
The compound according to claim 1, wherein Ar ₁ is a substituted or unsubstituted C ₆ -C ₄₀ aryl group, or a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms,
The C ₆ to C ₄₀ aryl group and the heteroaryl group having 5 to 40 nucleus atoms are each independently a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryl an amine group, C ₆ ~ C ₄₀ aryl phosphine oxide group, and a C ₆ ~ C ₄₀ substituted with or more selected from the group consisting of aryl silyl group one type of substituents or compounds characterized in that the unsubstituted.
The compound according to claim 1, wherein R ₁ to R ₁₀ are the same or different and each independently represents hydrogen, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, a substituted or unsubstituted 5 to 40 And a substituted or unsubstituted C ₆ to C ₄₀ arylamine group,
A C ₆ ~ C ₄₀ aryl group, nuclear atoms aryl of from 5 to 40 heteroaryl group, a C ₆ ~ C ₄₀ aryl amine groups are each independently a C over ₆ ~ one member selected from the aryl group consisting of the C ₄₀ substituent &Lt; / RTI &gt; or is unsubstituted.
2. The compound according to claim 1, wherein Ar &lt; _{1 &gt;} and Ar & And R ₁ to R ₁₀ are each independently selected from the group consisting of hydrogen, or a group of the substituents represented by the following S1 to S204.

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 the compound according to any one of claims 1 to 6.
The organic electroluminescent device according to claim 7, wherein at least one organic compound layer containing the compound is a light emitting layer.