KR20150141047A - Organic electro luminescence device - Google Patents

Abstract

The present invention provides an organic electroluminescent device, which comprises: a positive electrode; a negative electrode; and an organic matter layer with at least one layer interposed between the positive electrode and the negative electrode. At least one of the organic matter layers with at least one layer includes a first host and a second host. The purpose of the present invention is to provide an organic electroluminescent device with improved properties such as a driving voltage, light emitting efficiency, lifespan, etc.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescence device,

The present invention relates to an organic electroluminescent device including at least one organic material layer.

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.

In order to increase the luminous efficiency of the organic electroluminescent device, it is necessary to increase the color purity and to transfer energy. For this purpose, a luminescent material mixed with a host material and a dopant material can be used. 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, studies on the phosphorescent dopant as well as the phosphorescent host have been conducted. As a phosphorescent dopant material of the light emitting layer, metal complex compounds including Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like are known and CBP is known as a phosphorescent host material.

However, since conventional materials have low glass transition temperature and poor thermal stability, they are not satisfactory in terms of lifetime in an organic electroluminescent device. Therefore, development of an organic electroluminescent device including a luminescent material having excellent performance is required.

In order to solve the above problems, it is an object of the present invention to provide an organic electroluminescent device with improved driving voltage, luminous efficiency, and life span.

In order to achieve the above object, cathode; And at least one organic material layer interposed between the anode and the cathode, wherein at least one of the one or more organic material layers includes a first host and a second host, And the second host is a compound represented by the following general formula (2).

In Formula 1,

R ₁ to R ₇ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, and a substituted or unsubstituted C ₆ to C ₆₀ aryl group Selected,

a to c each independently represents an integer of 0 to 5,

d to g each independently represent an integer of 0 to 4,

n and m are each independently an integer of 0 to 1, provided that when n is 1, f is an integer of 0 to 3, and when m is 1, g is an integer of 0 to 3;

In Formula 2,

L ₁ to L ₃ are the same or different and are each independently a single bond, a substituted or unsubstituted C ₆ to C ₁₈ arylene group, or a substituted or unsubstituted heteroarylene group having 5 to 18 nucleus atoms ,

Ar ₁ to Ar ₃ are the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms With the proviso that Ar ₁ to Ar ₃ are all the same,

R ₈ to R ₁₀ are the same or different and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ of the alkynyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus of atoms of 3 to 40 heterocycloalkyl An alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, hwandoen C ₆ ~ C ₆₀ aryloxy group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl silyl group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl silyl group, a substituted or unsubstituted C ₁ ~ of a C ₄₀ alkyl boron group, a substituted or unsubstituted C ₆ ~ arylboronic group, a substituted or unsubstituted of C ₆₀ unsubstituted C ₁ ~ C ₄₀ phosphine group, It is selected from the group consisting of a ring or an unsubstituted C ₁ ~ C ₄₀ of the phosphine oxide group, and a substituted or unsubstituted C ₆ ~ C ₆₀ aryl amine,

o to q are each independently an integer of 0 to 1,

each of h to j is independently an integer of 0 to 4, provided that when o is 1, h is an integer of 0 to 3, and when p is 1, i is an integer of 0 to 3. When q is 1, j is 0 to 3 Lt; / RTI >

In the above L ₁ to L ₃ , R ₁ to R ₁₀ and Ar ₁ to Ar ₃ , an aryl group, a heteroarylene group, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, An aryl group, an aryloxy group, an aryloxy group, an aryloxy group, an aryloxy group, an aryloxy group, an oxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, a phosphine group, , C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atoms, heterocycloalkyl group of 3 to 40 of the, C ₆ ~ for C ₄₀ aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ aryl silyl group of C _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ of of C ₆₀ Ah It may be substituted with at least one member selected from the group consisting of an amine group.

Here, the organic material layer including the first host and the second host is preferably a phosphorescent light-emitting layer.

The light emitting layer preferably includes a metal complex compound dopant.

The organic electroluminescent device of the present invention comprises an organic material layer including a first host and a second host, wherein the first host and the second host are used in combination of the compound represented by the formula (1) and the compound represented by the formula (2) , The driving voltage of the device, the luminous efficiency and the life can be improved. Accordingly, when a display panel is manufactured using the organic electroluminescent device of the present invention, a display panel having improved performance and lifetime can be provided.

Hereinafter, the present invention will be described.

The organic electroluminescent device of the present invention includes a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the organic layers includes one or more of a first host and a second host , The first host is a compound represented by Formula 1, and the second host is a compound represented by Formula 2 below.

The compound represented by Formula 1, which is used as a first host in the present invention, is a 9-phenyl-carbazole, which may be substituted with deuterium, a C ₁ to C ₄₀ alkyl group, or a C ₆ to C ₆₀ aryl group. -9H-carbazole) basic skeleton is connected to one to three of them.

In general, the carbazole skeleton has electron donating group characteristics, which are electron donating and hole transporting properties.

In the compound represented by the formula (1), R ₁ to R ₃ are the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C _{6 Lt} ; / RTI > to C60. More specifically, R ₁ to R ₃ may be the same or different and each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, t-butyl, phenyl, biphenyl, have. The above-mentioned alkyl and aryl groups as substituents have electron donating and hole transporting properties, thereby enhancing the electron donating group characteristic in the molecule. In the present invention, it is preferable that R ₁ to R ₃ are each independently a phenyl group or biphenyl, and the bonding position of the phenyl group and the biphenyl group is not particularly limited and is not limited.

In the formula (1) according to the present invention, the 9-phenyl-9H-carbazole basic skeleton may be connected to one or more, for example, 1 to 3, and its bonding position is not particularly limited. At this time, it is preferable to bind at position 3 which is the main binding site of the carbazole. Also, when two carbazole skeletons are included in the molecule, they have high hole transportability, and the molecular weight is significantly increased as compared with one carbazole skeleton, resulting in high thermal stability. In particular, the basic skeleton of the 3, 3 'bonded biscarbazole form is the main binding site of the carbazole, and the two carbazoles can be firmly connected to enhance the thermal and electrical stability of the molecule itself. Therefore, it is preferable to use one or three carbazole.

The compound represented by the general formula (1) of the present invention can be further classified into a group of compounds represented by the following general formulas (1a) to (1c).

[Formula 1a]

(n=m=0)

(n = m = 0)

[Chemical Formula 1b]

(m=0, n=1)

(m = 0, n = 1)

[Chemical Formula 1c]

(n=m=1)

(n = m = 1)

In the above formulas (1a) to (1c)

R ₁ to R ₇ and a to g are the same as defined in formula (1).

More specifically, R ₁ to R ₃ are the same or different and are each independently a substituted or unsubstituted C ₆ to C ₆₀ aryl group,

R ₄ to R ₇ are preferably the same or different and are each independently hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, or a substituted or unsubstituted C ₆ to C ₆₀ aryl group .

The compound represented by the formula (1) of the present invention can be further specified as a group of compounds consisting of the following C-1 to C-61, but is not particularly limited thereto.

The compound represented by Formula 2, which is used as the second host of the present invention, is characterized by having a structure in which an aryl group or a heteroaryl group is bonded to a triphenylene basic skeleton.

Since the triphenylene skeleton has a high triplet energy, it is suitable for a phosphorescent host and has an electron donating group characteristic of electron donating and hole transporting properties.

The compound represented by the general formula (2) of the present invention is characterized in that at least one electron withdrawing group is bonded to the triphenylene moiety and has a bipolar structure. Such a bipolar compound can simultaneously combine the EDG capable of giving electrons and the EWG attracting electrons, so that the carrier does not deviate to one side and the imbalance of the exciton recombination caused by the fast movement of holes can be alleviated. Accordingly, when the compound represented by Formula 2 is used as the second host of the organic compound layer of the organic electroluminescent device, it can exhibit superior characteristics as the phosphorescent host material of the light emitting layer as compared with the conventional CBP.

The compound represented by the general formula (2) of the present invention can be further specified by the following general formulas (2a) to (2c).

(2a)

(2b)

[Chemical Formula 2c]

In Formulas (2a) to (2c), L ₁ to L ₃ and Ar ₁ to Ar ₃ are the same as defined in Formula (2).

In the compound represented by Formula 2, L ₁ to L ₃ are the same or different from each other and each independently represents a single bond, a substituted or unsubstituted C ₆ to C ₆₀ arylene group, and a substituted or unsubstituted nucleus And a heteroarylene group having 5 to 60 atoms. More specifically, it is preferable that L ₁ to L ₃ are the same or different and each independently selected from a single bond, phenylene, biphenylene, and carbazolylene.

Ar ₁ to Ar ₃ are the same or different and each independently represent hydrogen, deuterium, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus ≪ / RTI > In the present invention, at least one of Ar ₁ to Ar ₃ is preferably a heteroaryl group having 5 to 40 nuclear atoms and containing at least one element selected from the group consisting of N, O and S. In this case, the case where Ar ₁ to Ar ₃ are all the same is excluded. More specifically, an aryl group of Ar ₁ is C ₆ ~ C _40, Ar ₃ is is more preferred if 5 to 40 heteroaryl group of the nucleus atom.

Considering characteristics such as luminous efficiency, driving voltage and lifetime of the organic electroluminescent device, it is preferable that at least one of Ar ₁ to Ar ₃ in the general formula (2) used as the second host is a substituent represented by the following general formula (3).

(3)

In Formula 3,

L is selected from the group consisting of a single bond, a substituted or unsubstituted C ₆ -C ₁₈ arylene group, and a substituted or unsubstituted heteroarylene group having 5 to 18 nucleus atoms,

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

Wherein C (R ₁₁₎ a plurality of individual, if a plurality of R ₁₁ are the same or different and are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, a substituted or unsubstituted C ₁ ~ C _40, A substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted nucleus atom number of 5 to 60 heteroaryl group, a substituted or unsubstituted C ₆ ~ C ₆₀ of the aryloxy group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyloxy group, the substituted or unsubstituted C ₃ ~ cycloalkyl of C ₄₀ An alkyl group, a substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, a substituted or unsubstituted C ₆ to C ₆₀ arylamine group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, An unsubstituted C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a substituted or unsubstituted C ₆ to C ₆₀ arylphosphine group, A substituted or unsubstituted C ₆ to C ₆₀ arylphosphine oxide group, and a substituted or unsubstituted C ₆ to C ₆₀ arylsilyl group, which are bonded to adjacent groups to form a condensed ring And,

In the above L and R ₁₁ , an aryl group, a heteroarylene group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkoxy group, an aryloxy group, an aryloxy group, alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ of alkyloxy An arylamine group of C ₆ to C ₆₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group having a nucleus of 3 to 40, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ from the group consisting of C ₆₀ arylsilyl of And may be substituted or unsubstituted with at least one substituent selected. When there are a plurality of substituents, they may be the same or different.

In the substituent represented by the general formula (3), L is preferably a single bond, a phenylene group or a biphenylene group.

* Represents a moiety bonded to Formula 2, and when two or more of Z ₁ to Z ₅ are C (R ₁₁ ), a plurality of R _{11 s} may be the same as or different from each other.

More specifically, it is preferable that the substituent represented by the above-mentioned formula (3) is selected from the group consisting of substituents having the structures shown in the following A-1 to A-15.

In the above A-1 to A-15,

L and R < ₁₁ > are the same as defined in Formula 3,

R ₁₂ represents hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C ₁ -C ₄₀ alkyl, substituted or unsubstituted C ₂ -C ₄₀ alkenyl, substituted or unsubstituted C _2- an aryl group of C ₄₀ alkynyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus atom to C40 heterocycloalkyl group, a substituted or unsubstituted C ₆ ~ C ₆₀ of, A substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted C ₆ to C ₆₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted aryloxy group, a C ₆ ~ C ₆₀ aryl amine group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl silyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ group of an alkyl boron, substituted or unsubstituted C ₆ ~ C ₆₀ of the arylboronic group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl phosphine group, a substituted or unsubstituted C ₆ ~ C ₆₀ aryl ring of the phosphine oxide group, and a substituted or Is selected from the group consisting of aryl silyl unsubstituted C ₆ ~ C _60, or by combining groups to which they are contiguous and may form a condensed ring,

p is an integer of 1 to 4;

In R ₁₂ , the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, alkylsilyl group, alkylboron group, arylboron group , Arylphosphine group, arylphosphine oxide group and arylsilyl group are each independently selected from the group consisting of deuterium, halogen, cyano group, nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ aryl of C ₆₀ 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 ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide of the group and a C ₆ ~ value to one or more of the substituents selected from the group consisting of C ₆₀ aryl silyl Or it may be unsubstituted. When the substituents are plural, they may be the same or different.

In the compound represented by the general formula (2) according to the present invention, Ar ₁ to Ar ₃ and R ₈ to R ₁₀ may each independently be selected from the group consisting of hydrogen or the following substituent (functional group) (S1-S206) But is not limited thereto.

The compound represented by the general formula (2) of the present invention may be embodied as a group of compounds consisting of the following D-1 to D-34, but is not particularly limited thereto.

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, hexyl And the like.

The alkenyl in the present invention 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, Isopropenyl, 2-butenyl, and the like.

Alkynyl in the present invention 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- 2-propynyl, and the like.

The 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 phenyl, naphthyl, phenanthryl, anthryl and the like.

The 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, the ring may be pendant or condensed with each other, or may be condensed 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 is 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 alkyloxy in the present invention is a monovalent substituent group represented by R'O-, wherein R 'is an alkyl having 1 to 40 carbon atoms and includes 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.

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

The 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 of the ring, preferably 1 to 3 carbons, is N, O, S or Se. ≪ / RTI > Examples of such heterocycloalkyl include morpholine, piperazine and the like.

The alkylsilyl in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, and arylsilyl means silyl substituted with aryl having 5 to 40 carbon atoms.

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

In the organic electroluminescent device of the present invention configured as described above, at least one of the plurality of organic layers includes the first host and the second host to balance the holes and electrons injected into the device, have. Here, the mixing ratio of the first host and the second host is not particularly limited in the production of the organic material layer, but the first host and the second host may be mixed in a weight ratio of 1:99 to 99: 1.

In the organic electroluminescent device of the present invention, the light emitting layer may be a single light emitting layer or may have a plurality of light emitting layers to realize a mixed color thereof. More specifically, in the present invention, a plurality of light emitting layers may be sequentially stacked between a hole transporting layer and an electron transporting layer to realize a mixed color thereof when voltage and current are applied.

As described above, the stacked organic electroluminescent device of the present invention including a plurality of light emitting layers or a plurality of light emitting layers including a plurality of different materials between the hole transporting layer and the electron transporting layer can be realized by implementing a mixed color upon application of voltage and current, The light emitting efficiency can be increased by the number of the light emitting layers.

Meanwhile, the organic compound layer of the present invention including the first host and the second host is preferably a light emitting layer, and the light emitting layer of the present invention may include a dopant together with the first host and the second host. Here, the dopant included in the light emitting layer may be a dopant that is known in the art without limitation. For example, it is preferable to use a metal complex compound containing iridium (Ir).

The method for producing the light emitting layer including the first host, the second host and the dopant described above can be manufactured without specific limitation according to a method known in the art. Hereinafter, two preferred embodiments for manufacturing the light emitting layer will be exemplified below. However, it is not particularly limited.

A first method among the two embodiments is a co-deposition method in which a first host and a second host are placed in first and second heat sources, respectively, and a dopant is placed in a third heat source and heat is applied to form a light emitting layer.

More specifically, a second host having a high hole mobility and a high hole injection efficiency is placed in a first heat source at a vacuum degree of 1 x 10 ^-06 torr or less, and electron mobility ) Is high and a second host having a good electron injection efficiency is positioned and the dopant and the evaporation rate per second of the third heat source are adjusted to co-deposit at a proper ratio. At this time, the number of co-deposited hosts may be two or more depending on the characteristics of the light emitting layer.

The amount of the first host, the second host and the dopant is not particularly limited. For example, the first host and the second host may be used in an amount of 70 to 99% by weight and the dopant may be used in an amount of 1 to 30% by weight. More specifically, it is preferable to use 80 to 95% by weight of the first host and the second host and 5 to 20% by weight of the dopant.

In a second method of the above two embodiments, in order to reduce the number of heat sources used and simplify the formation process, the first host and the second host used for forming the light emitting layer are mixed at a proper ratio, Emitting layer is formed.

More specifically, the host (first host + second host) mixed in the first heat source is placed at a degree of vacuum of 1 x 10 ^-06 or less, the dopant is placed in the second heat source, . Such a second method can reduce the error in mixing ratio occurring when one or more hosts are used and can form a light emitting layer with a small number of heat sources.

The amount of the first host, the second host and the dopant is not particularly limited. For example, the first host and the second host may be used in an amount of 70 to 99% by weight and the dopant may be used in an amount of 1 to 30% by weight. More specifically, it is preferable to use 80 to 95 wt% of the first host and the second host and 5 to 20 wt% of the dopant.

The material usable as the anode included in the organic electroluminescent device of the present invention is not particularly limited, but examples thereof 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, 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 and polyaniline; And carbon black.

Examples of materials usable as an anode included in the organic electroluminescent device of the present invention include, but are not limited to, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, , Alloys thereof, and multi-layered materials such as LiF / Al and LiO ₂ / Al.

The structure of the organic electroluminescent device of the present invention is not particularly limited and examples thereof include a structure in which a substrate, an anode, an organic material layer (a hole injecting layer -> hole transporting layer -> light emitting layer -> electron transporting layer) Lt; / RTI > 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 the compound represented by Formula 1 as a first host.

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 insulating layer or an adhesive layer is inserted into the interface between the anode and the cathode and the organic layer.

The organic electroluminescent device of the present invention may be formed using materials and methods known in the art, except that one or more layers (for example, a light emitting layer) of the organic material layer include the first host and the second host. An organic material layer can be formed.

Meanwhile, the substrate used in the production of the organic electroluminescent device of the present invention is not particularly limited, but examples thereof include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.  

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

[Preparation Example 1] Synthesis of IIC-1

<Step 1> Synthesis of IIC-1

(27.8 g, 113 mmol), (9H-carbazol-3-yl) boronic acid (23.8 g, 113 mmol), K ₂ CO ₃ (46.8 g, 339 mmol) and THF / H ₂ O were mixed (400 ml / 100 ml) into the _{following, Pd (PPh 3) 4 (} 6.53 g, 5.65 mmol) was stirred at 80 ℃ for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain IIC-1 (30 g, yield 80%).

¹ H-NMR of IIC-1:? 7.29-7.50 (m, 5H), 7.94 (d,

[Preparation Example 2] Synthesis of IIC-2

<Step 1> Synthesis of IIC-2

(24.9 g, 77.4 mmol), (6-phenyl-9H-carbazol-3-yl) boronic acid (22.2 g, 77.4 mmol), K ₂ CO ₃ 32.0 g, 232 mmol) and THF / H ₂ O (400 ml / 100 ml) were mixed. Pd (PPh ₃ ) ₄ (4.47 g, 3.86 mmol) was added thereto and stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain IIC-2 (30 g, yield 80%).

¹ H-NMR of IIC-2:? 7.29-7.50 (m, 10H), 7.92 (s,

[Preparation Example 3] Synthesis of IIC-3

<Step 1> Synthesis of IIC-3

(22.6 g, 91.8 mmol), 9-phenyl-9H-carbazol-3-yl) boronic acid (26.4 g, 91.8 mmol), K ₂ CO ₃ (38.1 g, 275 mmol) and a mixture of _{THF / H 2 O (400 ml} / 100 ml) , then insert the _{Pd (PPh 3) 4 (5.31} g, 4.59 mmol) was stirred at 80 ℃ for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain IIC-3 (30 g, yield 80%).

Of ^{IIC-3 1 H-NMR:} δ 7.29-7.50 (m, 15H), 7.92 (d, 1H), 7.94 (d, 1H), 8.00 (s, 1H), 8.03 (s, 1H), 10.1 (s , 1H)

[Preparation Example 4] Synthesis of IIC-4

Synthesis of 9 - ([1,1 ': 3', 1 "-terphenyl] -5'-yl) -3-bromo-9H-carbazole

(39.7 g, 111 mmol), 3-bromo-9H-carbazole (27.4 g, 111 mmol), Pd (OAc) ₂ 1.25 g, 5.57 mmol), NaO (t-Bu) (21.4 g, 223 mmol), P (t-Bu) 3 (50wt%) (4.51 g, 11.1 mmol) and a mixture of Toluene (100 ml) and 110 ℃ Lt; / RTI &gt; for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, and then water was removed with MgSO ₄ and purified by column chromatography to obtain the desired compound 9 - ([1,1 ': 3', 1 "-terphenyl] -5'-yl ) -3-bromo-9H-carbazole (31.7 g, 60%).

^{1 H-NMR: δ 7.07-7.35 (} m, 18H), 7.92 (d, 1H), 7.98 (s, 1H)

<Step 2> Synthesis of IIC-4

Carbazole (31.7 g, 66.9 mmol), (9H-carbazol-3-yl) -3-bromo-9H- yl) boronic acid (14.1 g, 66.9 mmol), K 2 CO 3 (27.7 g, 200 mmol) and a mixture of _{THF / H 2 O (400 ml} / 100 ml) , and _{then, Pd (PPh 3) 4 (} 3.86 g , 3.34 mmol), which was stirred for 12 hours at 80 ° C.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain IIC-4 (30 g, yield 80%).

^{1 H-NMR: δ 7.05-7.33 (} m, 18H), 7.38-7.42 (m, 5H), 7.92 (d, 1H), 7.94 (d, 1H), 8.00 (s, 1H), 8.03 (s, 1H ), 10.1 (s, 1 H)

[Preparation Example 5] Synthesis of IIC-5

<Step 1> Synthesis of 3-bromo-6,9-diphenyl-9H-carbazole

(35.9 g, 111 mmol), iodobenzene (22.7 g, 111 mmol), Pd (OAc) ₂ (1.25 g, 5.57 mmol), NaO (t-Bu) (21.4 g, 223 mmol), P (t-Bu) ₃ (50 wt%) (4.51 g, 11.1 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography to remove moisture with MgSO _{4. The} objective compound 3-bromo-6,9-diphenyl-9H-carbazole (31.7 g, 60%) was obtained.

^{1 H-NMR: δ 7.07-7.35 (} m, 14H), 7.92 (s, 1H), 7.98 (s, 1H)

<Step 2> Synthesis of IIC-5

(26.2 g, 66.9 mmol), 6-phenyl-9H-carbazol-3-yl) boronic acid (19.2 g, 66.9 mmol), K ₂ CO ₃ (27.7 g, 200 mmol) and THF / H ₂ O (400 ml / 100 ml) were mixed and Pd (PPh ₃ ) ₄ (3.86 g, 3.34 mmol) was added thereto and stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain IIC-5 (30 g, yield 80%).

¹ H-NMR:? 7.05-7.33 (m, 15H), 7.38-7.42 (m, 8H), 7.92 (s, ), 10.3 (s, 1 H)

[Preparation Example 6] Synthesis of IIC-6

<Step 1> Synthesis of IIC-6

(30.8 g, 77.4 mmol), (9H-carbazol-3-yl) boronic acid (16.3 g, 77.4 mmol), K ₂ CO ₃ (32.1 g, , 232 mmol) and THF / H ₂ O (400 ml / 100 ml) were mixed. Pd (PPh ₃ ) ₄ (4.47 g, 3.87 mmol) was added thereto and stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain IIC-6 (30 g, yield 80%).

¹ H-NMR:? 7.05-7.33 (m, 10H), 7.38-7.42 (m, 9H), 7.92 ), 10.1 (s, 1 H)

[Preparation Example 7] Synthesis of IIC-7

<Step 1> Synthesis of IIC-7

(24.9 g, 77.4 mmol), 9-phenyl-9H-carbazol-3-yl boronic acid (22.2 g, 77.4 mmol), K ₂ CO ₃ 32.1 g, 232 mmol) and THF / H ₂ O (400 ml / 100 ml) were mixed. Pd (PPh ₃ ) ₄ (4.47 g, 3.87 mmol) was added thereto and stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain IIC-7 (30 g, yield 80%).

^{1 H-NMR: δ 7.03-7.29 (} m, 10H), 7.38-7.42 (m, 9H), 7.94 (s, 1H), 7.96 (s, 1H), 7.98 (s, 1H), 8.01 (s, 1H ), 10.2 (s, 1 H)

[Preparation Example 8] Synthesis of IIC-8

<Step 1> Synthesis of 9- (biphenyl-3-yl) -3-bromo-9H-carbazole

3-iodobiphenyl (39.7 g, 111 mmol), 3-bromo-9H-carbazole (27.4 g, 111 mmol), Pd (OAc) ₂ (1.25 g, 5.57 mmol), NaO g, 223 mmol), P (t-Bu) ₃ (50 wt%) (4.51 g, 11.1 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography to remove moisture with MgSO _{4. The} desired compound 9- (biphenyl-3-yl) -3-bromo-9H- ).

^{1 H-NMR: δ 7.25-7.52 (} m, 12H), 7.94 (d, 1H), 8.07 (m, 2H), 8.55 (d, 1H)

<Step 2> Synthesis of IIC-8

(26.9 g, 67.7 mmol), (9H-carbazol-3-yl) boronic acid (14.1 g, 66.9 mmol), K ₂ CO ₃ (27.7 g, 200 mmol) and THF / H ₂ O (400 ml / 100 ml) were mixed and Pd (PPh ₃ ) ₄ (3.86 g, 3.34 mmol) was added thereto and stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain IIC-8 (24.6 g, yield 75%).

^{1 H-NMR: δ 7.29 (} t, 2H), 7.46-7.69 (m, 13H), 7.77 (s, 2H), 7.87-8.18 (m, 6H), 10.1 (s, 1H)

[Preparation Example 9] Synthesis of TP-1

<Step 1> Synthesis of TP-1

(40.3 g, 104 mmol), phenylboronic acid (12.7 g, 104 mmol), K ₂ CO ₃ (43.3 g, 313 mmol) and THF / H ₂ O (400 ml / 100 ml) Pd (PPh ₃ ) ₄ (6.03 g, 5.21 mmol) was added thereto, followed by stirring at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 10: 1 (v / v)) to obtain TP-1 (20 g, yield 50%).

¹ H-NMR of TP-1:? 7.05-7.24 (m, 13H), 7.35 (m, 2H)

[Preparation Example 10] Synthesis of TP-2

<Step 1> Synthesis of 3-bromo-9-phenyl-6- (triphenylen-2-yl) -9H-carbazole

(48.1 g, 120 mmol), Triphenylen-2-ylboronic acid (32.6 g, 120 mmol), K ₂ CO ₃ (49.7 g, 360 mmol) and 3,6-Dibromo-9- a mixture of _{THF / H 2 O (400 ml} / 100 ml) , then insert the _{Pd (PPh 3) 4 (6.93} g, 6.00 mmol) was stirred at 80 ℃ for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain 3-Bromo-9-phenyl-6- (triphenylen- g, yield 50%).

^{1 H-NMR: δ 7.05-7.24 (} m, 16H), 7.35-7.45 (m, 4H), 7.94 (s, 1H), 7.98 (s, 1H)

<Step 2> Synthesis of TP-2

3-Bromo-9-phenyl-6- (triphenylen-2-yl) -9H-carbazole (32.9 g, 60.0 mmol), 4,4,4 ' dioxaborolane (15.2 g, 60.0 mmol), Pd (dppf) Cl ₂ (4.89 g, 6.00 mmol), KOAc (17.7 g, 180 mmol) and 1,4-Dioxane (400 ml) were mixed and stirred at 120 ° 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 purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain TP-2 (25.0 g, yield 70%) .

¹ TP-2 H-NMR: δ 1.24 (s, 12H), 7.01-7.20 (m, 16H), 7.30-7.37 (m, 4H), 7.90 (s, 1H), 7.93 (s, 1H)

[Preparation Example 11] Synthesis of TP-3

<Step 1> Synthesis of TP-3

(23.5 g, 95.3 mmol), Triphenylen-2-ylboronic acid (26 g, 95.3 mmol), K ₂ CO ₃ (39.5 g, 286 mmol) and THF / H ₂ O a mixture of 400 ml / 100 ml) in the _{following, Pd (PPh 3) 4 (} 5.51 g, 4.77 mmol) into a 80 ℃ was stirred for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain TP-3 (30 g, yield 80%).

¹ H-NMR:? 7.01-7.20 (m, 11H), 7.30-7.37 (m, 5H), 7.92

[Preparation Example 12] Synthesis of TP-4

<Step 1> Synthesis of 2- (3,5-Dibromophenyl) triphenylene

(53.9 g, 149 mmol), triphenylen-2-ylboronic acid (40.5 g, 149 mmol), K ₂ CO ₃ (61.7 g, 447 mmol) and THF / H ₂ O (400 ml / 100 ml) were mixed, Pd (PPh ₃ ) ₄ (8.60 g, 7.44 mmol) was added thereto, and the mixture was stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain 2- (3,5-Dibromophenyl) triphenylene (34.4 g, yield 50%).

^{1 H-NMR: δ 7.07-7.23 (} m, 11H), 7.45 (s, 2H), 7.72 (s, 1H)

<Step 2> Synthesis of 3- (3-Bromo-5- (triphenylen-2-yl) phenyl) -9-phenyl-9H-carbazole

Carbodi-3-yl) boronic acid (21.4 g, 74.4 mmol), K ₂ CO ₃ (30.9 g, 74.4 mmol) was added to a solution of 2- (3,5-Dibromophenyl) triphenylene g, 224 mmol) and THF / H ₂ O (400 ml / 100 ml) were mixed. Pd (PPh ₃ ) ₄ (4.30 g, 3.72 mmol) was added thereto and stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain 3- (3-Bromo-5- (triphenylen- 9H-carbazole (23.2 g, yield 50%).

^{1 H-NMR: δ 7.02-7.28 (} m, 17H), 7.35-7.40 (m, 5H), 7.42 (s, 1H), 7.45 (s, 1H), 7.92 (s, 1H), 7.96 (s, 1H )

<Step 3> Synthesis of TP-4

9-phenyl-9H-carbazole (23.2 g, 37.2 mmol), 4,4,4 ', 4', 5,5 (trifluoromethyl) (9.33 g, 37.2 mmol), Pd (dppf) Cl ₂ (3.03 g, 3.72 mmol), KOAc (10.9 g, 3.72 mmol), 5 ', 5'-octamethyl-2,2'- , 112 mmol) and 1,4-dioxane (300 ml) were mixed and stirred at 120 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain TP-4 (20 g, yield 80% .

¹ H-NMR of TP-4:? 1.24 (s, 12H), 7.04-7.26 (m, 19H), 7.32-7.39

[Preparation Example 13] Synthesis of TP-5

Synthesis of 3-Bromo-9-phenyl-6- (3- (triphenylen-2-yl) phenyl) -9H-carbazole

(29.9 g, 74.4 mmol), (3- (Triphenylen-2-yl) phenyl) boronic acid (25.9 g, 74.4 mmol), K ₂ CO ₃ (30.9 g, 224 mmol) and a mixture of _{THF / H 2 O (400 ml} / 100 ml) , then insert the _{Pd (PPh 3) 4 (4.30} g, 3.72 mmol) was stirred at 80 ℃ for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. After removing the solvent from the obtained organic layer, the residue was purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to give 3-Bromo-9-phenyl- 6- (3- (triphenylen- 9H-carbazole (23.2 g, yield 50%).

^{1 H-NMR: δ 7.02-7.28 (} m, 17H), 7.35-7.40 (m, 7H), 7.93 (s, 1H), 7.98 (s, 1H)

<Step 2> Synthesis of TP-5

3-Bromo-9-phenyl-6- (triphenylen-2-yl) phenyl) -9H-carbazole (23.2 g, 37.2 mmol), 4,4,4,4,5,5 (9.33 g, 37.2 mmol), Pd (dppf) Cl ₂ (3.03 g, 3.72 mmol), KOAc (10.9 g, 3.72 mmol), 5 ', 5'-octamethyl-2,2'- , 112 mmol) and 1,4-dioxane (300 ml) were mixed and stirred at 120 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain TP-5 (20 g, yield 80% .

TP-5 ¹ H-NMR of: δ 1.24 (s, 12H) , 7.04-7.26 (m, 17H), 7.32-7.39 (m, 7H), 7.93 (s, 1H), 7.95 (s, 1H)

[Preparation Example 14] Synthesis of TP-6

<Step 1> Synthesis of 3- (3- (triphenylen-2-yl) phenyl) -9H-carbazole

3-bromo-9H-carbazole (18.31 g, 74.4 mmol), (3- (triphenylen-2-yl) phenyl) boronic acid (25.9 g, 74.4 mmol), K ₂ CO ₃ (30.9 g, 224 mmol ) And THF / H ₂ O (400 ml / 100 ml) were mixed. Pd (PPh ₃ ) ₄ (4.30 g, 3.72 mmol) was added thereto and stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain 17.47 g of 3- (3- (triphenylen-2-yl) phenyl) -9H- 50%).

¹ H-NMR:? 7.29 (t, 1H), 7.48-7.88 (m, 13H), 8.04-8.18 (m, 5H), 8.93 (d, 2H), 9.15 (s, 1 H)

[Preparation Example 15] Synthesis of TP-7

<Step 1> Synthesis of 3- (3 '- (triphenylen-2-yl) biphenyl-3-yl) -9H-carbazole

3- (3-bromophenyl) -9H-carbazole (23.88 g, 74.4 mmol), 3- (triphenylen-2-yl) phenyl boronic acid (25.9 g, 74.4 mmol), K ₂ CO ₃ g, 224 mmol) and THF / H ₂ O (400 ml / 100 ml) were mixed. Pd (PPh ₃ ) ₄ (4.30 g, 3.72 mmol) was added thereto and stirred at 80 ° C for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and the residue was purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to give 3- (triphenylen-2-yl) biphenyl- (22.18 g, yield 55%).

¹ of the TP-7 H-NMR: δ 7.28 (t, 1H), 7.48-7.88 (m, 17H), 8.04-8.18 (m, 5H), 8.92 (d, 2H), 9.17 (s, 1H), 10.2 (s, 1 H)

[Synthesis Example 1] Synthesis of C-1

(5 g, 15.0 mmol), 4-bromo-1,1'-biphenyl (7.01 g, 30.1 mmol), Pd (OAc) ₂ (338 mg, 1.50 mmol), NaO ) (5.78 g, 60.2 mmol), P (t-Bu) ₃ (50 wt%) (1.22 g, 3.01 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography to remove water with MgSO ₄ to obtain the desired compound C-1 (6.70 g, 70%).

Mass (theory: 636.78 g / mol, measurement: 636 g / mol)

[Synthesis Example 2] Synthesis of C-2

The procedure of Synthetic Example 1 was repeated except that 3-bromo-1,1'-biphenyl (7.02 g, 30.1 mmol) was used instead of 4-bromo-1,1'- -2 (6.70 g, yield 70%).

Mass (theory: 636.78 g / mol, measurement: 636 g / mol)

[Synthesis Example 3] Synthesis of C-3

Was obtained in the same manner as in Synthesis Example 1, except that 5'-bromo-1,1 ': 3', 1 "-terphenyl (9.30 g, 30.1 mmol) was used in place of 4-bromo-1,1'- To obtain the target compound C-3 (8.31 g, yield 70%).

Mass (theory: 788.97 g / mol, measurement: 788 g / mol)

[Synthesis Example 4] Synthesis of C-4

Iodobenzene (4.21 g, 20.6 mmol), Pd (OAc) ₂ (232 mg, 1.03 mmol), NaO (t-Bu) (3.96 g, 41.2 mmol), IIC- P (t-Bu) ₃ (50 wt%) (836 mg, 2.06 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography to remove the water with MgSO ₄ to obtain the desired compound C-4 (4.60 g, 70%).

Mass (theory: 636.78 g / mol, measurement: 636 g / mol)

[Synthesis Example 5] Synthesis of C-5

(5.70 g, yield 70%) was obtained in the same manner as in Synthesis Example 4, except that 4-bromo-1,1'-biphenyl (4.82 g, 20.6 mmol) ).

Mass (theory: 788.97 g / mol, measurement: 788 g / mol)

[Synthesis Example 6] Synthesis of C-6

(5.70 g, yield 70%) was obtained in the same manner as in Synthesis Example 4, except that 3-bromo-1,1'-biphenyl (4.82 g, 20.6 mmol) ).

Mass (theory: 788.97 g / mol, measurement: 788 g / mol)

[Synthesis Example 7] Synthesis of C-7

The procedure of Synthetic Example 4 was repeated except that 5'-bromo-1,1 ': 3', 1 "-terphenyl (6.38 g, 20.6 mmol) was used instead of iodobenzene, 7 (5.70 g, yield 70%).

Mass (theory: 941.16 g / mol, measured: 941 g / mol)

[Synthesis Example 8] Synthesis of C-8

(2.85 g, 12.2 mmol), Pd (OAc) ₂ (232 mg, 0.612 mmol), NaO (t-Bu ) (2.35 g, 24.5 mmol), P (t-Bu) ₃ (50 wt%) (495 mg, 1.22 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography to remove the water with MgSO ₄ to obtain the desired compound C-8 (4.80 g, 70%).

Mass (calculated: 560.69 g / mol, measured: 560 g / mol)

[Synthesis Example 9] Synthesis of C-9

The procedure of Synthetic Example 8 was repeated except that 3-bromo-1,1'-biphenyl (2.85 g, 12.2 mmol) was used instead of 4-bromo-1,1'- -9 (4.80 g, yield 70%).

Mass (calculated: 560.69 g / mol, measured: 560 g / mol)

[Synthesis Example 10] Synthesis of C-10

Was obtained in the same manner as in Synthesis Example 8, except that 5'-bromo-1,1 ': 3', 1 "-terphenyl (4.82 g, 20.6 mmol) was used in place of 4-bromo-1,1'- To obtain the target compound C-10 (5.46 g, yield 70%).

Mass (theory: 636.78 g / mol, measurement: 636 g / mol)

[Synthesis Example 11] Synthesis of C-11

(2.0 g, 8.92 mmol), Pd (OAc) ₂ (100 mg, 0.446 mmol), NaO (t-Bu ) (1.71 g, 17.8 mmol), P (t-Bu) ₃ (50 wt%) (361 mg, 0.892 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography using MgSO ₄ to remove the desired compound C-11 (4.45 g, 70%).

Mass (theory: 712.88 g / mol, measurement: 712 g / mol)

[Synthesis Example 12] Synthesis of C-12

The procedure of Synthesis Example 11 was repeated except that 3-bromo-1,1'-biphenyl (2.08 g, 8.92 mmol) was used instead of 4-bromo-1,1'- -12 (4.45 g, yield 70%).

Mass (theory: 712.88 g / mol, measurement: 712 g / mol)

[Synthesis Example 13] Synthesis of C-13

(2.0 g, 8.92 mmol), Pd (OAc) ₂ (100 mg, 0.446 mmol), NaO (t-Bu ) (1.71 g, 17.8 mmol), P (t-Bu) ₃ (50 wt%) (361 mg, 0.892 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO ₄ and purified by column chromatography to obtain the target compound C -13 (4.45 g, 70% ).

Mass (theory: 712.88 g / mol, measurement: 712 g / mol)

[Synthesis Example 14] Synthesis of C-14

The procedure of Synthesis Example 11 was repeated except that 3-bromo-1,1'-biphenyl (2.08 g, 8.92 mmol) was used instead of 4-bromo-1,1'- -14 (4.45 g, yield 70%).

Mass (theory: 712.88 g / mol, measurement: 712 g / mol)

[Synthesis Example 15] Synthesis of C-15

(2.41 g, 10.3 mmol), Pd (OAc) ₂ (116 mg, 0.516 mmol), NaO (t-Bu ) (1.98 g, 20.6 mmol), P (t-Bu) ₃ (50 wt%) (418 mg, 1.03 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography to remove moisture with MgSO ₄ to obtain the desired compound C-15 (4.60 g, 70%).

Mass (theory: 636.78 g / mol, measurement: 636 g / mol)

[Synthesis Example 16] Synthesis of C-16

The procedure of Synthesis Example 15 was repeated except that 3-bromo-1,1'-biphenyl (2.41 g, 10.3 mmol) was used in place of 4-bromo-1,1'- -16 (4.60 g, yield 70%).

Mass (theory: 636.78 g / mol, measurement: 636 g / mol)

[Synthesis Example 17] Synthesis of C-17

Except that 5'-bromo-1,1 ': 3', 1 "-terphenyl (3.19 g, 10.3 mmol) was used in place of 4-bromo-1,1'- To obtain the target compound C-17 (5.15 g, yield 70%).

Mass (theory: 712.88 g / mol, measurement: 712 g / mol)

[Synthesis Example 18] Synthesis of C-18

Iodobenzene (2.10 g, 10.3 mmol), Pd (OAc) ₂ (116 mg, 0.516 mmol), NaO (t-Bu) (1.98 g, 20.6 mmol), IIC- P (t-Bu) ₃ (50 wt%) (418 mg, 1.03 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography to remove moisture with MgSO ₄ to obtain the desired compound C-18 (4.05 g, 70%).

Mass (calculated: 560.69 g / mol, measured: 560 g / mol)

[Synthesis Example 19] Synthesis of C-19

(4.60 g, yield 70%) was obtained in the same manner as in Synthesis Example 18, except that 4-bromo-1,1'-biphenyl (2.41 g, 10.3 mmol) ).

Mass (theory: 636.78 g / mol, measurement: 636 g / mol)

[Synthesis Example 20] Synthesis of C-20

(4.60 g, yield 70%) was obtained by carrying out the same procedure as in Synthesis Example 18, except that 3-bromo-1,1'-biphenyl (2.41 g, 10.3 mmol) ).

Mass (theory: 636.78 g / mol, measurement: 636 g / mol)

[Synthesis Example 21] Synthesis of C-21

The same procedure as in Synthesis Example 18 was conducted, except that 5'-bromo-1,1 ': 3', 1 "-terphenyl (3.19 g, 10.3 mmol) was used in place of iodobenzene, 21 (5.15 g, yield 70%).

Mass (theory: 712.88 g / mol, measurement: 712 g / mol)

[Synthesis Example 22] Synthesis of C-22

(2.0 g, 8.92 mmol), Pd (OAc) ₂ (100 mg, 0.446 mmol), NaO (t-Bu ) (1.71 g, 17.8 mmol), P (t-Bu) ₃ (50 wt%) (361 mg, 0.892 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography to remove water with MgSO ₄ to obtain the desired compound C-7 (3.68 g, yield 65%).

Mass (theory: 636.78 g / mol, measurement: 636 g / mol)

[Synthesis Example 23] Synthesis of D-1

(5 g, 13.0 mmol), (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid (4.61 g, 13.0 mmol), K _{2 CO 3 (5.41 g, 39.1 mmol} ) and a mixture of _{THF / H 2 O (80 ml} / 20 ml) , then insert the _{Pd (PPh 3) 4 (754} mg, 0.652 mmol) was stirred at 80 ℃ for 12 hours .

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain D-1 (6.38 g, yield 80%).

Mass (theory: 611.73 g / mol, measurement: 611 g / mol)

[Synthesis Example 24] Synthesis of D-2

 (3'- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid was used instead of (3- (4,6-diphenyl-1,3,5- The procedure of Synthetic Example 1 was repeated, except that D-2 (7.18 g, 13.0 mmol) was used, except that [- [1,1'-biphenyl] -3-yl) boronic acid , Yield: 80%).

Mass (theory: 687.83 g / mol, measurement: 687 g / mol)

[Synthesis Example 25] Synthesis of D-3

 ((4 '- (4,6-diphenyl-1,3,5-triazin-2-yl) 3-yl) boronic acid (5.60 g, 13.0 mmol) was used in place of D- (1,1'-biphenyl- g, yield: 80%).

Mass (theory: 687.83 g / mol, measurement: 687 g / mol)

[Synthesis Example 26] Synthesis of D-4

2-chloro-4,6-diphenyl-1,3,5-triazine (2.25 g, 8.40 mmol) and K ₂ CO ₃ (3.48 g, 25.2 mmol) and it was stirred for 12 hours in a mixture of _{THF / H 2 O (80 ml} / 20 ml) , and then, Pd (PPh _{3) 4} into a (485 mg, 0.420 mmol) 80 ℃.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain D-4 (4.71 g, yield 80%).

Mass (theory: 700.83 g / mol, measurement: 700 g / mol)

[Synthesis Example 27] Synthesis of D-5

The procedure of Synthesis Example 4 was repeated except that 2-chloro-4,6-diphenylpyrimidine (2.24 g, 8.40 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5- To obtain the objective compound D-5 (4.71 g, yield 80%).

Mass (theory: 699.84 g / mol, measurement: 699 g / mol)

[Synthesis Example 28] Synthesis of D-6

The procedure of Synthesis Example 4 was repeated except that 4-chloro-2,6-diphenylpyrimidine (2.24 g, 8.40 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5- To obtain the target compound D-6 (4.71 g, yield 80%).

Mass (theory: 699.84 g / mol, measurement: 699 g / mol)

[Synthesis Example 29] Synthesis of D-7

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (2.89 g, 8.40 mmol) instead of 2-chloro-4,6-diphenyl- , The target compound B-4 (5.22 g, yield 80%) was obtained by carrying out the same procedure as in Synthesis Example 4.

Mass (theory: 776.92 g / mol, measurement: 776 g / mol)

[Synthesis Example 30] Synthesis of D-8

Except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (2.89 g, 8.40 mmol) was used in place of 2-chloro-4,6-diphenyl-1,3,5- The target compound D-8 (5.22 g, yield 80%) was obtained.

Mass (calculated: 775.93 g / mol, measured: 775 g / mol)

[Synthesis Example 31] Synthesis of D-9

2-chloro-4,6-diphenyl-1,3,5-triazine (3.74 g, 14.0 mmol) and Pd (OAc) ₂ (143 mg, 0.635 mmol) in a nitrogen stream. ), NaO (t-Bu) (2.44 g, 25.4 mmol), P (t-Bu) ₃ (50 wt%) (514 mg, 1.27 mmol) and Toluene (100 ml) Respectively. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography using water (MgSO ₄ ) to obtain the desired compound D-9 (5.56 g, 70%).

Mass (theory: 624.73 g / mol, measurement: 624 g / mol)

[Synthesis Example 32] Synthesis of D-10

The same procedure as in Synthesis Example 9 was carried out except that 4-chloro-2,6-diphenylpyrimidine (3.74 g, 14.0 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5- To obtain the target compound D-10 (5.56 g, yield 70%).

Mass (theory: 623.74 g / mol, measurement: 623 g / mol)

[Synthesis Example 33] Synthesis of D-11

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.81 g, 14.0 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5- , The target compound D-11 (6.23 g, yield 70%) was obtained by carrying out the same procedure as in Synthesis Example 9.

Mass (theory: 700.83 g / mol, measurement: 700 g / mol)

[Synthesis Example 34] Synthesis of D-12

Except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.81 g, 14.0 mmol) was used in place of 2-chloro-4,6-diphenyl-1,3,5- The target compound D-12 (6.23 g, yield 70%) was obtained.

Mass (theory: 699.84 g / mol, measurement: 699 g / mol)

[Synthesis Example 35] Synthesis of D-13

2-chloro-4,6-diphenyl-1,3,5-triazine (1.99 g, 7.44 mmol) and K ₂ CO ₃ (3.08 g, 22.3 mmol) and it was stirred for 12 hours in a mixture of _{THF / H 2 O (80 ml} / 20 ml) , and then, Pd (PPh ₃₎ into a _{4 (430 mg, 0.372 mmol)} 80 ℃.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane: MC = 5: 1 (v / v) to obtain D-13 (4.63 g, yield 80%).

Mass (theory: 776.92 g / mol, measurement: 776 g / mol)

[Synthesis Example 36] Synthesis of D-14

The procedure of Synthesis Example 13 was repeated except that 4-chloro-2,6-diphenylpyrimidine (1.99 g, 7.44 mmol) was used instead of 2-chloro-4,6-diphenyl- To obtain the target compound D-14 (4.63 g, yield 80%).

Mass (calculated: 775.93 g / mol, measured: 775 g / mol)

[Synthesis Example 37] Synthesis of D-15

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (2.56 g, 7.44 mmol) was used instead of 2-chloro-4,6-diphenyl- , The target compound D-15 (5.08 g, yield 80%) was obtained by carrying out the same procedure as in Synthesis Example 13.

Mass (theory: 853.02 g / mol, measurement: 853 g / mol)

[Synthesis Example 38] Synthesis of D-16

Except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (2.56 g, 7.44 mmol) was used in place of 2-chloro-4,6-diphenyl-1,3,5- The target compound D-16 (5.08 g, yield 80%) was obtained.

Mass (theory: 852.03 g / mol, measured: 852 g / mol)

[Synthesis Example 39] Synthesis of D-17

2-chloro-4,6-diphenyl-1,3,5-triazine (1.99 g, 7.44 mmol) and K ₂ CO ₃ (3.08 g, 22.3 mmol) and it was stirred for 12 hours in a mixture of _{THF / H 2 O (80 ml} / 20 ml) , and then, Pd (PPh ₃₎ into a _{4 (430 mg, 0.372 mmol)} 80 ℃.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain D-17 (4.63 g, yield 80%).

Mass (theory: 776.92 g / mol, measurement: 776 g / mol)

[Synthesis Example 40] Synthesis of D-18

The procedure of Synthesis Example 17 was repeated except that 4-chloro-2,6-diphenylpyrimidine (1.99 g, 7.44 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5- To obtain the target compound D-18 (4.63 g, yield 80%).

Mass (calculated: 775.93 g / mol, measured: 775 g / mol)

[Synthesis Example 41] Synthesis of D-19

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (2.56 g, 7.44 mmol) was used instead of 2-chloro-4,6-diphenyl- , The target compound D-19 (5.08 g, yield 80%) was obtained by conducting the same procedure as in Synthesis Example 17.

Mass (theory: 853.02 g / mol, measured: 853 g / mol)

[Synthesis Example 42] Synthesis of D-20

Except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (2.56 g, 7.44 mmol) was used in place of 2-chloro-4,6-diphenyl-1,3,5- The target compound D-20 (5.08 g, yield 80%) was obtained.

Mass (theory: 852.03 g / mol, measured: 852 g / mol)

[Synthesis Example 43] Synthesis of D-22

2-chloro-4,6-diphenyl-1,3,5-triazine (3.74 g, 14.0 mmol) and Pd (OAc) ₂ (143 mg, 0.635 mmol) in a nitrogen stream. ), NaO (t-Bu) (2.44 g, 25.4 mmol), P (t-Bu) ₃ (50 wt%) (514 mg, 1.27 mmol) and Toluene (100 ml) Respectively. Extracted with ethyl acetate. After the reaction was terminated, and then, dried with MgSO _4, and purified by column chromatography to obtain the title compound D-22 (5.78g, 65% ).

Mass (theory: 700.83 g / mol, measurement: 700 g / mol)

[Synthesis Example 44] Synthesis of D-25

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.81 g, 14.0 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5- , The target compound D-25 (6.41 g, yield 70%) was obtained by carrying out the same procedure as in Synthesis Example 43.

Mass (theory: 776.92 g / mol, measurement: 776 g / mol)

[Synthesis Example 45] Synthesis of D-27

(6.92 g, 12.7 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.74 g, 14.0 mmol) and Pd (OAc) ₂ (143 mg, 0.635 mmol) ), NaO (t-Bu) (2.44 g, 25.4 mmol), P (t-Bu) ₃ (50 wt%) (514 mg, 1.27 mmol) and Toluene (100 ml) Respectively. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography to remove moisture with MgSO ₄ to obtain the desired compound D-27 (6.61 g, 68%).

Mass (theory: 776.92 g / mol, measurement: 776 g / mol)

[Synthesis Example 46] Synthesis of D-28

2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.81 g, 14.0 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5- , The target compound D-28 (7.04 g, yield 65%) was obtained by carrying out the same procedure as in Synthesis Example 45.

Mass (theory: 853.02 g / mol, measured: 853 g / mol)

[Synthesis Example 47] Synthesis of D-31

Except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.81 g, 14.0 mmol) was used in place of 2-chloro-4,6-diphenyl-1,3,5- The target compound D-31 (6.41 g, yield 70%) was obtained.

Mass (calculated: 775.93 g / mol, measured: 775 g / mol)

[Synthesis Example 48] Synthesis of D-32

Except that 2- (3-chlorophenyl) -4,6-diphenylpyrimidine (4.81 g, 14.0 mmol) was used in place of 2-chloro-4,6-diphenyl-1,3,5- To obtain the target compound D-32 (6.41 g, yield 70%).

Mass (calculated: 775.93 g / mol, measured: 775 g / mol)

[Synthesis Example 49] Synthesis of D-33

Except that 2- (3-chlorophenyl) -4,6-diphenylpyridine (4.81 g, 14.0 mmol) was used in place of 2-chloro-4,6-diphenyl-1,3,5- (D-33) (6.41 g, yield 70%).

Mass (theory: 774.95 g / mol, measurement: 774 g / mol)

[Synthesis Example 50] Synthesis of D-34

Except that 2- (3-chlorophenyl) -4,6-diphenylpyrimidine (4.81 g, 14.0 mmol) was used in place of 2-chloro-4,6-diphenyl-1,3,5- The target compound D-34 (7.04 g, yield 65%) was obtained.

Mass (theory: 852.03 g / mol, measured: 852 g / mol)

[Synthesis Example 51] Synthesis of C-49

<Step 1> Synthesis of 3,6-di (biphenyl-4-yl) -9H-carbazole

A solution of 10.0 g (30.8 mmol) of 3,6-dibromo-9H-carbazole, 18.3 g (92.3 mmol) of biphenyl-4-ylboronic acid, 6.16 g (154.0 mmol) of NaOH and 200 ml / 100 ml of THF / H ₂ O were added and stirred. At 40 ℃ into the Pd (PPh _{3) 4} of 1.78 g (5 mol%) 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, 3,6-di (biphenyl-4-yl) -9H-carbazole (10.9 g, 23.1 mmol, yield 75%) was obtained by column chromatography.

^{1 H-NMR (DMSO):} δ 7.35 (t, 2H), 7.47 (t, 4H), 7.57 (d, 2H), 7.73 (d, 4H), 7.78 (m, 6H), 7.89 (d, 4H) , 8.66 (s, 2H), 11.42 (s, 1 H)

<Step 2> Synthesis of C-49

4-yl) -9H-carbazole (7.06 g, 15.0 mmol), 4-bromo-1,1'-biphenyl (9.24 g, 30.1 mmol), Pd (OAc) ₂ (338 mg, 1.50 mmol), NaO (t-Bu) (5.78 g, 60.2 mmol), P (t-Bu) 3 (50wt%) (1.22 g, 3.01 mmol) and a mixture of Toluene (100 ml) and 110 Lt; 0 &gt; C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography to remove the water with MgSO ₄ to obtain the desired compound C-49 (7.96 g, 70%).

Mass (theory: 699.88 g / mol, measurement: 699 g / mol)

[Synthesis Example 52] Synthesis of C-53

3,6-dibromo-9-phenyl- 9H-carbazole (3.69 g, 9.18 mmol) in a nitrogen stream, 9-phenyl-9H-carbazol -3-ylboronic acid (5.79 g, 20.2 mmol), K 2 CO 3 (7.62 g, 55.0 mmol) and a mixture of _{THF / H 2 O (40 ml} / 10 ml) , then insert the _{Pd (PPh 3) 4 (1.062} g, 0.918 mmol) was stirred at 80 ℃ for 12 hours.

After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to obtain C-53 (5.32 g, yield 80%).

Mass (calculated: 725.88 g / mol, measured: 725 g / mol)

[Examples 1 to 28] Preparation of Organic Electroluminescent Device

The glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was ultrasonically cleaned with distilled water. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech), and then the substrate was cleaned using UV for 5 minutes The substrate was transferred to a vacuum evaporator.

M-MTDATA (60 nm) / TCTA (80 nm) / 2 was prepared by using C-4 as the first host and the compounds of Synthetic Examples 23 to 50 as the second host on the ITO transparent substrate prepared as described above. by laminating the 90% of the first host and the second host _{+ 10% Ir (ppy) 3} (300nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) in order Thereby preparing an organic electroluminescent device.

At this time, the structures of m-MTDATA, TCTA, Ir (ppy) ₃ and BCP used were as follows, and the mixing ratio of the first host and the second host was 5: 5.

[Examples 29 to 51] Preparation of organic electroluminescent device

Example 1 MTDATA (60) was prepared by using the following C-1 to C-22, C-49 and C-53 as the first host and the compound represented by D-25 as the second host on the ITO transparent substrate prepared as above. nm) / TCTA (80 nm) / 90% of the first host and the second host _{+ 10% Ir (ppy) 3} (30nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

The structure of m-MTDATA, TCTA, Ir (ppy) ₃ and BCP was the same as in Example 1, and the mixing ratio of the first host and the second host was 5: 5.

[Examples 52 to 54] Preparation of organic electroluminescent device

Example 1 MTDATA (60 nm) / TCTA (80 nm) / 90% of the ITO transparent substrate prepared above, using the C-4 as the first host and the compound represented by D-25 as the second host The first host and the second host were laminated in the order of 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al The device was fabricated.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ and BCP used were the same as those of Example 1, and the mixing ratios of the first host and the second host were adjusted as shown in Table 1 below.

[Comparative Example 1] Production of organic electroluminescent device

An organic electroluminescent device was fabricated in the same manner as in Example 1, except that 90% of CBP + 10% Ir (ppy) ₃ was used in forming the light emitting layer. At this time, the structure of CBP used is as follows.

[Comparative Example 2] Production of organic electroluminescent device

An organic electroluminescent device was fabricated in the same manner as in Example 1 except that 90% of the second host (D-25) + 10% Ir (ppy) ₃ was used for forming the light emitting layer.

[Comparative Example 3] Production of organic electroluminescent device

An organic electroluminescent device was fabricated in the same manner as in Example 1 except that 90% of the first host (C-4) + 10% Ir (ppy) ₃ was used for forming the light emitting layer.

[Experimental Example]

The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 1 to 54 and Comparative Examples 1 to 3, and the results are shown in Table 1 below.

Sample Host usage rate The driving voltage (V) Current efficiency (cd / A) Example 1 50% C-4 + 50% D-1 6.30 42.9 Example 2 50% C-4 + 50% D-2 6.40 41.8 Example 3 50% C-4 + 50% D-3 6.10 43.9 Example 4 50% C-4 + 50% D-4 6.40 42.0 Example 5 50% C-4 + 50% D-5 6.20 42.5 Example 6 50% C-4 + 50% D-6 6.35 42.2 Example 7 50% C-4 + 50% D-7 6.25 42.3 Example 8 50% C-4 + 50% D-8 6.20 42.7 Example 9 50% C-4 + 50% D-9 6.25 43.0 Example 10 50% C-4 + 50% D-10 6.15 42.7 Example 11 50% C-4 + 50% D-11 6.20 42.0 Example 12 50% C-4 + 50% D-12 6.25 41.5 Example 13 50% C-4 + 50% D-13 6.25 43.0 Example 14 50% C-4 + 50% D-14 6.10 42.2 Example 15 50% C-4 + 50% D-15 5.95 42.9 Example 16 50% C-4 + 50% D-16 5.95 43.1 Example 17 50% C-4 + 50% D-17 6.00 43.3 Example 18 50% C-4 + 50% D-18 6.05 43.2 Example 19 50% C-4 + 50% D-19 6.15 42.8 Example 20 50% C-4 + 50% D-20 6.10 42.9 Example 21 50% C-4 + 50% D-22 6.10 42.1 Example 22 50% C-4 + 50% D-25 6.35 43.5 Example 23 50% C-4 + 50% D-27 6.15 43.2 Example 24 50% C-4 + 50% D-28 6.20 42.2 Example 25 50% C-4 + 50% D-31 6.20 42.9 Example 26 50% C-4 + 50% D-32 6.15 42.6 Example 27 50% C-4 + 50% D-33 6.10 41.4 Example 28 50% C-4 + 50% D-34 6.20 42.0 Example 29 50% C-1 + 50% D-25 6.20 42.5 Example 30 50% C-2 + 50% D-25 6.40 41.8 Example 31 50% C-3 + 50% D-25 6.35 41.9 Example 32 50% C-5 + 50% D-25 6.40 42.4 Example 33 50% C-6 + 50% D-25 6.30 42.5 Example 34 50% C-7 + 50% D-25 6.30 42.6 Example 35 50% C-8 + 50% D-25 6.35 42.5 Example 36 50% C-9 + 50% D-25 6.30 42.9 Example 37 50% C-10 + 50% D-25 6.35 43.0 Example 38 50% C-11 + 50% D-25 6.25 42.7 Example 39 50% C-12 + 50% D-25 6.30 42.9 Example 40 50% C-13 + 50% D-25 6.15 42.5 Example 41 50% C-14 + 50% D-25 6.20 43.2 Example 42 50% C-15 + 50% D-25 6.20 43.0 Example 43 50% C-16 + 50% D-25 6.25 42.9 Example 44 50% C-17 + 50% D-25 6.30 43.1 Example 45 50% C-18 + 50% D-25 6.10 42.3 Example 46 50% C-19 + 50% D-25 6.15 43.0 Example 47 50% C-20 + 50% D-25 6.15 42.8 Example 48 50% C-21 + 50% D-25 6.10 42.9 Example 49 50% C-22 + 50% D-25 6.00 43.0 Example 50 50% C-49 + 50% D-25 6.40 40.5 Example 51 50% C-53 + 50% D-25 6.40 40.9 Example 52 80% C-4 + 20% D-25 6.10 43.1 Example 53 60% C-4 + 40% D-25 6.15 42.7 Example 54 40% C-4 + 60% D-25 6.25 42.5 Comparative Example 1 CBP 6.93 38.2 Comparative Example 2 D-25 6.55 40.3 Comparative Example 3 C-4 6.40 35.2

The organic electroluminescent devices of the present invention (Examples 1 to 54) using the light emitting layer including the first host and the second host were prepared by using CBP, C-4 and D-25 as a single host material It was confirmed that the organic electroluminescent device of Comparative Examples 1 to 3, which uses the light emitting layer including the light emitting layer, exhibits excellent performance in current efficiency and driving voltage.

Claims (9)

anode; cathode; And at least one organic material layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a first host and a second host,
Wherein the first host is a compound represented by the following general formula (1)
Wherein the second host is a compound represented by the following formula (2).
[Chemical Formula 1]

In Formula 1,
R ₁ to R ₇ are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, and a substituted or unsubstituted C ₆ to C ₆₀ aryl group Selected,
a to c each independently represents an integer of 0 to 5,
d to g each independently represent an integer of 0 to 4,
n and m are each independently an integer of 0 to 1, provided that when n is 1, f is an integer of 0 to 3, and when m is 1, g is an integer of 0 to 3;
(2)

In Formula 2,
L ₁ to L ₃ are the same or different and each independently represents a single bond, a substituted or unsubstituted C ₆ to C ₁₈ arylene group, or a substituted or unsubstituted heteroarylene group having 5 to 18 nucleus atoms Selected,
Ar ₁ to Ar ₃ are the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms Except that Ar ₁ to Ar ₃ are all the same,
R ₈ to R ₁₀ are the same or different and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ ~ C ₄₀ of the alkynyl group, a substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, a substituted or unsubstituted nucleus of atoms of 3 to 40 hetero A substituted or unsubstituted C ₁ to C ₆₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C ₁ to C ₄₀ alkyloxy group, An unsubstituted C ₆ to C ₆₀ aryloxy group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted C ₆ to C ₆₀ arylsilyl group, a substituted or unsubstituted C ₁ ~ C ₄₀ alkyl group of boron, phosphorous substituted or unsubstituted C ₆ ~ arylboronic group, a substituted or unsubstituted of C ₆₀ unsubstituted C ₁ ~ C ₄₀ pingi, A substituted or unsubstituted C ₁ to C ₄₀ phosphine oxide group and a substituted or unsubstituted C ₆ to C ₆₀ arylamine group,
o to q are each independently an integer of 0 or 1,
each of h to j is independently an integer of 0 to 4, provided that when o is 1, h is an integer of 0 to 3, and when p is 1, i is an integer of 0 to 3. When q is 1, j is 0 to 3 Lt; / RTI &gt;
A heteroaryl group, an aryl group, a heteroaryl group, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxycarbonyl group or an alkyloxycarbonyl group in the above-mentioned L ₁ to L ₃ , R ₁ to R ₁₀ and Ar ₁ to Ar ₃ , A halogen group, a cyano group, a nitro group, a cyano group, a cyano group, a cyano group, a nitro group, a cyano group, a nitro group, A C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, an amino group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, C ₆ ~ aryl of C ₆₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of C ₆ ~ C _60, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ phosphine oxide of a C ₄₀ group, and An arylamine group having ₆ to ₆₀ carbon atoms, and an arylamine group having ₆ to ₆₀ carbon atoms. The method according to claim 1,
The organic electroluminescent device of claim 1, wherein the first host is represented by any one of the following formulas (1a) to (1c).
[Formula 1a]

[Chemical Formula 1b]

[Chemical Formula 1c]

In the above formulas (1a) to (1c)
R ₁ to R ₇ and a to g are the same as defined in claim 1. 3. The method of claim 2,
R ₁ to R ₃ are the same or different and are each independently a substituted or unsubstituted C ₆ to C ₆₀ aryl group,
R ₄ to R ₇ are the same or different and are each independently hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, or a substituted or unsubstituted C ₆ to C ₆₀ aryl group The organic electroluminescent device comprising: The method according to claim 1,
Wherein the second host is represented by any one of the following Chemical Formulas (2a) to (2c).
(2a)

(2b)

[Chemical Formula 2c]

In the general formulas (2a) to (2c), L ₁ to L ₃ and Ar ₁ to Ar ₃ are the same as defined in the above-mentioned item (1). The method according to claim 1,
Wherein at least one of Ar ₁ to Ar ₃ of the second host is a substituent represented by the following general formula (3).
(3)

In Formula 3,
L is a single bond, a substituted or unsubstituted C ₆ -C ₁₈ arylene group, or a substituted or unsubstituted heteroarylene group having 5 to 18 nucleus atoms,
Z ₁ to Z ₅ are the same or different and each independently N or C (R ₁₁ ), wherein at least one of Z ₁ to Z ₅ is N,
Wherein C (R ₁₁₎ a, and a plurality if individual plural R ₁₁ are the same or different from each other, R ₁₁ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, a substituted or unsubstituted C ₁ ~ C ₄₀ ring A substituted or unsubstituted C ₂ to C ₄₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted A heteroaryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a substituted or unsubstituted C ₃ to C ₄₀ cycloalkyl group, a substituted Or a heterocycloalkyl group having 3 to 40 unsubstituted nuclear atoms, a substituted or unsubstituted C ₆ to C ₆₀ arylamine group, a substituted or unsubstituted C ₁ to C ₄₀ alkylsilyl group, a substituted or unsubstituted A C ₁ to C ₄₀ alkylboron group, a substituted or unsubstituted C ₆ to C ₆₀ arylboron group, a substituted or unsubstituted C ₆ to C ₆₀ arylphosphine A substituted or unsubstituted C ₆ to C ₆₀ arylphosphine oxide group, and a substituted or unsubstituted C ₆ to C ₆₀ arylsilyl group, or they may be bonded to adjacent groups to form a condensed ring Lt; / RTI &gt;
In R ₁₁ , the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkylboron group, arylboron group A halogen atom, a cyano group, a nitro 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 arylthio group, C ₂ to C ₄₀ alkynyl groups, C ₆ to C ₆₀ aryl groups, heteroaryl groups having 5 to 60 nuclear atoms, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group ₁ ~ C ₄₀ alkyl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ at least one selected from the group consisting of C ₆₀ aryl silyl &Lt; / RTI &gt; anode; cathode; And at least one organic material layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a first host and a second host,
Wherein the first host is a compound represented by the following formula (1b)
And the second host is a compound represented by the following formula (2b).
[Chemical Formula 1b]

In the above formula (1b)
R ₁ , R ₃ to R ₄ and R ₇ are the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted C ₁ to C ₄₀ alkyl group and a substituted or unsubstituted C ₆ to C ₆₀ An aryl group,
a and c are each independently an integer of 0 to 5,
d and g are each independently an integer of 0 to 4;
(2b)

In the above formula (2b)
L ₁ and L ₂ are the same or different and each independently represents a single bond, a substituted or unsubstituted C ₆ -C ₁₈ arylene group, or a substituted or unsubstituted heteroarylene group having 5 to 18 nucleus atoms Selected,
Ar ₁ and Ar ₂ are the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted C ₆ to C ₄₀ aryl group, and a substituted or unsubstituted heteroaryl group having 5 to 40 nucleus atoms Except that Ar ₁ and Ar ₂ are all the same,
When the arylene group, the heteroarylene group, the aryl group or the heteroaryl group is substituted for each of L ₁ to L ₂ and Ar ₁ to Ar ₂ , each independently selected from the group consisting of deuterium, a halogen group, a cyano group, a nitro group, an amino group, a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 hetero cycloalkyl group, C ₆ ~ C ₄₀ A C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ aryl group, a substituted or unsubstituted aryl group having 5 to 40 nuclear atoms, aryl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₁ ~ C ₄₀ of the phosphine group, C ₁ ~ C ₄₀ phosphine oxide group, and a C ₆ ~ C ₆₀ of &Lt; / RTI &gt;&lt; RTI ID = 0.0 &gt; arylamine &lt; / RTI &gt; 7. The method according to claim 1 or 6,
Wherein a mixing ratio of the first host and the second host is 1 to 99: 99 to 1 weight ratio. 7. The method according to claim 1 or 6,
Wherein the organic material layer including the first host and the second host is a phosphorescent light-emitting layer. 7. The method according to claim 1 or 6,
Wherein the light emitting layer comprises a dopant, and the dopant is a metal complex compound.