KR20160078125A - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic electroluminescent device comprising a novel compound having heat resistance, hole transporting ability, electron inhibiting ability, and the like in at least one organic matter layer, thereby improving properties such as a light-emitting efficiency, a driving voltage, durability, etc.

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 and an organic electroluminescent device including the same.

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

The luminescent material may be classified into blue, green, and red luminescent materials depending on the luminescent color. In addition, it can be classified into yellow and orange light emitting materials necessary for realizing a better color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting 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. The development of phosphorescent materials can theoretically improve luminescence efficiency up to four times that of fluorescence, so attention is focused on phosphorescent host materials as well as phosphorescent dopants.

Up to now, hole injecting layer, hole transporting layer. NPB, BCP, Alq ₃ and the like are widely known as materials used as a hole blocking layer and an electron transporting layer, and anthracene derivatives as a luminescent material have been reported as a fluorescent dopant / host material. Particularly, as a phosphorescent material having a great advantage in improving the efficiency of a light emitting material, there are metal complex compounds including Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ , , And is used as a red dopant material. So far, CBP has shown excellent properties as a phosphorescent host material.

However, conventional luminescent materials are good in terms of luminescence characteristics, but have poor thermal stability due to low glass transition temperature, and thus are not satisfactory in terms of lifetime in organic EL devices. Therefore, development of an organic electroluminescent device including a luminescent material having excellent performance is required.

In addition, in order to realize practical use and improve the characteristics of the organic electroluminescent device, not only the device should be composed of the organic material layer having the multilayer structure, but also the material of the device, especially the hole transporting material, should have stable thermal and electrical characteristics. This is because, when a voltage is applied to a device, molecules having low thermal stability due to heat generated in the device have a low crystal stability and are rearranged. As a result, a localized crystallization occurs and an inhomogeneous portion exists. Thereby causing deterioration and destruction of the device.

Therefore, in consideration of the above-mentioned points, conventionally used hole transport materials include m-MTDATA [4,4 ', 4 "-tris (N-3- methylphenyl- Triphenylamine], TPD [N, N'-diphenyl-N, N'-di ( 3-methylphenyl) -4,4'-diaminobiphenyl] and NPB [N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine].

However, since m-MTDATA and 2-TNATA have low glass transition temperatures (Tg) of 78 ° C and 108 ° C, respectively, they cause problems in mass-production. On the other hand, since TPD and NPB have low glass transition temperatures (Tg) of 60 占 폚 and 96 占 폚, respectively, there is a fatal disadvantage that the lifetime of the device is shortened. Therefore, development of an organic electroluminescent device capable of increasing thermal stability and having an excellent hole transporting capability and capable of increasing the luminous efficiency and power efficiency of the organic electroluminescent device is desired.

Japanese Patent Application Laid-Open No. 2001-160489

An object of the present invention is to provide a compound which is excellent in both electron-blocking ability and hole-transporting ability and can be used as a light-emitting layer material, a light-emitting auxiliary layer material, and a hole transport layer material.

Another object of the present invention is to provide an organic electroluminescent device including the above-described novel compound, which has low driving voltage, high luminous efficiency, and improved lifetime.

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

(In the formula 1,

a is an integer from 0 to 5;

b is an integer from 0 to 3;

c is an integer from 0 to 4;

R ₁ to R ₄ are the same or different and are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms , A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 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 ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C of ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine An oxy group and an arylamine group of C ₆ to C ₆₀ , or may combine with adjacent substituents to form a condensed aromatic ring or a condensed heteroaromatic ring;

Provided that at least one of R ₁ to R ₄ is a substituent represented by the following formula (2);

In Formula 2,

* Is a moiety in which at least one of R ₁ to R ₄ in formula (1) is bonded;

L ₁ is a single bond or a heteroarylene group having 5 to 60 ring atoms and an arylene group having ₆ to ₆₀ carbon atoms;

Ar ₁ and Ar ₂ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms and a C ₆ to C ₆₀ And Ar ₁ and Ar ₂ may be bonded to each other to form a ring,

Alkyl group of Ar ₁ to Ar _2, an aryl group, a heteroaryl group and an arylamine group, R ₁ to the alkyl group of R _4, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkyl An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, a heteroarylene group of L ₁ may be deuterium, halogen, cyano, C ₁ - a C ₄₀ alkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 of the cycloalkyl of the alkyl group, the number of nuclear atoms of 3 to 40 heteroaryl group, C ₁ ~ C ₄₀ C ₆ -C ₆₀ aryloxy groups, C ₁ -C ₄₀ alkylsilyl groups, C ₆ -C ₆₀ arylsilyl groups, C ₁ -C ₄₀ alkylboron groups, C ₆ -C ₆₀ the arylboronic group, C ₆ ~ C ₆₀ aryl phosphine value as pingi, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ at least one selected from the group consisting of aryl amine group of C ₆₀ Substituted or unsubstituted, and, if the beach, where the substituent of the plurality, all of which are the same or different from each other).

The present invention also provides an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers is a compound And an organic electroluminescent device.

According to an example, the one or more organic layers including the compound represented by Formula 1 may be selected from the group consisting of a hole transport layer, a light emitting auxiliary layer, and a light emitting layer.

Since the organic electroluminescent device of the present invention includes at least one organic compound layer having excellent heat resistance, light emitting ability and hole transporting ability in at least one organic layer, aspects such as light emitting performance, driving voltage, lifetime and efficiency can be greatly improved, And can be effectively applied to a full color display panel and the like.

Hereinafter, the present invention will be described.

The compound according to the present invention is characterized in that the phenyl skeleton of the phenylcarbazole moiety to which the phenyl group is introduced at the 1-position of the carbazole is bonded to the basic skeleton of the phenyl group moiety, either of the two benzene moieties of the carbazole and the nitrogen moiety of the carbazole And a structure in which an arylamine group-containing substituent is introduced into one molecule, which is characterized by being represented by the above formula (1). Here, the position number of the carbazole can be represented as follows.

In the compound according to the present invention, the compound molecule is distorted by introducing the phenyl group into the 1-position of the carbazole, so that there is no problem of lowering the luminescence property due to pi-pi-stacking. Therefore, the compound of the present invention can prevent the formation of an exciton excimer (excimer), thereby improving the luminous efficiency of the OLED. In addition, since the compound of the present invention has a lower deposition temperature than that of a carbazole compound into which a phenyl group is not introduced by introducing a phenyl group into the 1-position of the carbazole, the thermal stability of the molecule can be enhanced.

In addition, the light emitting layer generally includes a host and a dopant to increase color purity and luminous efficiency. At this time, the host material should have a higher triplet energy gap than the dopant in the host. In particular, in order for the dopant to provide effective phosphorescence, the lowest excitation state of the host should be higher energy than the lowest emission state of the dopant. However, in the compounds of the present invention, the phenylcarbazole moiety has a broad singlet energy level and a high triplet energy level. Therefore, when the compound of the present invention is applied as a host of the light emitting layer, the light emitting performance of the OLED can be improved because it can exhibit a higher energy level than the dopant.

In addition, since the compound of the present invention has a high triplet energy gap as described above, the excitons generated in the light emitting layer can be prevented from diffusing (moving) into the adjacent hole transporting layer. Therefore, when the organic compound layer (hereinafter referred to as "light-emission-assisting layer") is formed between the hole transporting layer and the light-emitting layer using the compound of the present invention, the diffusion of the excitons is prevented by the compound, Unlike a conventional organic electroluminescent device, the number of the excitons contributing to light emission in the light emitting layer substantially increases, and the light emitting efficiency of the device can be improved.

In addition, both the arylamine group and the carbazole group are electron donating groups (EDGs), which are thermally stable and have excellent hole mobility. Therefore, the compound of the present invention containing an arylamine group-containing substituent and a carbazole moiety has excellent thermal stability and high hole mobility, so that when the compound is used as a hole transporting material of an OLED, .

In addition, since the compound represented by the formula (1) of the present invention introduces various substituents into the basic skeleton, the molecular weight of the compound is significantly increased, and thus the glass transition temperature is improved. Therefore, the conventional CBP (4,4-dicarbazolylbiphenyl) And exhibits higher thermal stability. Further, the compound of the present invention is also effective in inhibiting crystallization of the organic material layer.

Thus, when the compound of the present invention is applied to an organic material layer of an organic electroluminescent device, preferably a light emitting layer material, a hole transporting layer material, or a light emitting auxiliary layer material, the performance and lifetime characteristics of the organic electroluminescent device can be greatly improved . Such an organic electroluminescent device can consequently maximize the performance of a full-color organic luminescent panel.

In the formula (1) according to the present invention, when a is 0, hydrogen is not substituted by substituent R ₁ , and when a is an integer of 1 to 5, R ₁ is as defined in the above formula (1). When b is 0, it means that hydrogen is not substituted with substituent R ₂ , and when b is an integer of 1 to 3, R ₂ is the same as defined in Formula 1. When c is 0, hydrogen means not substituted by substituent R ₃ , and when c is an integer of 1 to 4, R ₃ is the same as defined in formula (1). At this time, if R ₁ is a plurality, these are the same or different, and, if R ₂ is plural, if they are the same or different and, R ₃ are each other plurality, which are the same or different from each other.

Wherein R ₁ to R ₄ are the same or different and are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₂₀ alkyl, C ₃ to C ₂₀ cycloalkyl, An alkyl group, a C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₁ to C ₂₀ alkyloxy group, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₂₀ alkylsilyl group, C ₆ ~ C ₄₀ aryl silyl group, C ₁ ~ C ₂₀ 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 it is selected from the group consisting pin oxide groups and C ₆ ~ C ₄₀ aryl amines are preferred. Or preferably R ₁ -R ₂ , R ₂ -R ₃ , R ₃ -R ₄ and / or R ₄ -R ₁ are bonded to each other to form a condensed aromatic ring or a heterocyclic ring containing a heteroatom selected from N, P and S To form a condensed heteroaromatic ring.

More preferably, R ₁ to R ₄ are the same or different and each independently selected from the group consisting of C ₆ to C ₄₀ aryl groups, heteroaryl groups having 5 to 40 nuclear atoms, and C ₆ to C ₄₀ arylamine groups Can be selected from the group.

Provided that at least one of R ₁ to R ₄ is a substituent represented by the general formula (2).

In Formula 2, L ₁ is preferably a single bond or a group selected from the group consisting of an arylene group having ₆ to ₂₀ carbon atoms and a heteroarylene group having 5 to 40 nuclear atoms.

Wherein Ar ₁ and Ar ₂ are the same or different and each independently represents a C ₁ to C ₂₀ alkyl group, a C ₆ to C ₄₀ aryl group, and a heteroaryl group having 5 to 40 nuclear atoms and / A C ₆ to C ₄₀ arylamine group, or Ar ₁ and Ar ₂ are bonded to each other to form a condensed ring.

An alkyl group, an aryl group, a heteroaryl group and an arylamine group of Ar ₁ to Ar ₂ ; R ₁ to the alkyl group of R _4, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, An arylphosphine oxide group, an arylamine group; The allylene group and heteroarylene group of L ₁ may be substituted by deuterium, halogen, cyano, a C ₁ to C ₄₀ alkyl group (preferably a C ₁ to C ₂₀ alkyl group), a C ₃ to C ₄₀ cycloalkyl group ₃ or a cycloalkyl group of C _20), the number of nuclear atoms of 3 to 40 heterocycloalkyl group (preferably of, can be from 3 to 20 heterocycloalkyl group), C ₆ ~ C ₆₀ aryl group (preferably a nuclear atom, C ₆ ~ aryl), heteroaryl of nuclear atoms of 5 to 60 of the C ₄₀ aryl group (preferably, a group of nuclear atoms of 5 to 40 heteroaryl group), C ₁ ~ C ₄₀ alkyloxy the time (preferably of, C ₁ ~ C alkyloxy group of _20), C ₆ ~ C ₆₀ aryloxy the time (preferably of, C ₆ ~ aryloxy C _40), C the ₁ ~ C ₄₀ alkyl silyl group (preferably a, C of ₁ ~ C ₂₀ Alkylsilyl group), an arylsilyl group of C ₆ to C ₆₀ (preferably an arylsilyl group of C ₆ to C ₄₀ ), a C ₁ to C ₄₀ alkylboron group (preferably a C ₁ to C ₂₀ alkylboron group), C ₆ ~ C ₆₀ aryl boron group (preferably of, C ₆ ~ C ₄₀ The arylboronic group), C ₆ ~ C ₆₀ aryl phosphine group (preferably, C ₆ ~ C ₄₀ aryl phosphine group), C ₆ ~ C ₆₀ aryl phosphine oxide groups (preferably, C ₆ ~ C ₄₀ of (Preferably 1 to 3 substituents) selected from the group consisting of an arylamine group (preferably an arylphosphine oxide group) and an arylamine group of C ₆ to C ₆₀ (preferably, an arylamine group of C ₆ to C ₄₀ ) ≪ / RTI > At this time, when a plurality of substituents are present, they are the same or different.

Examples of the substituent represented by the formula (2) include, but are not limited to, a substituent represented by the following formula (3).

In Formula 3,

L ₁ , Ar ₁ and Ar ₂ are as defined in the above formula (2)

Z ₂ is a single bond or is selected from the group consisting of O, S, and N (R ₅ )

R ₅ is preferably selected from the group consisting of hydrogen, deuterium (D), a C ₁ to C ₄₀ alkyl group (preferably a C ₁ to C ₂₀ alkyl group), a C ₆ to C ₆₀ aryl group (preferably a C ₆ to C ₃₀ aryl group , A heteroaryl group having 5 to 60 nuclear atoms (preferably a heteroaryl group having 5 to 30 nuclear atoms) and an arylamine group having ₆ to ₆₀ carbon atoms (preferably a C ₆ to C ₃₀ arylamine group ), Or may combine with adjacent substituents to form a condensed aromatic ring or a condensed heteroaromatic ring;

The aryl, heteroaryl and arylamine groups of R ₅ are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ -C ₄₀ alkyl (preferably C ₁ -C ₂₀ alkyl), C ₃ -C ₄₀ A cycloalkyl group (preferably a C ₃ to C ₂₀ cycloalkyl group), a heterocycloalkyl group having 3 to 40 nuclear atoms (preferably a heterocycloalkyl group having 3 to 20 nuclear atoms), a C ₆ to C ₆₀ aryl group (Preferably a C ₆ to C ₃₀ aryl group), a heteroaryl group having 5 to 60 nuclear atoms (preferably a heteroaryl group having 5 to 30 nuclear atoms), a C ₁ to C ₄₀ alkyloxy group Preferably a C ₁ to C ₂₀ alkyloxy group), a C ₆ to C ₆₀ aryloxy group (preferably a C ₆ to C ₃₀ aryloxy group), a C ₁ to C ₄₀ alkylsilyl group , An alkylsilyl group of C ₁ to C ₂₀ ), an arylsilyl group of C ₆ to C ₆₀ (preferably a C ₆ to C ₃₀ arylsilyl group), a C ₁ to C ₄₀ alkylboron group (preferably C ₁ - alkyl group of boron _{C 20), C 6 ~ C} 60 Arylboronic group (preferably, C group ₆ to arylboronic of C _30), C ₆ to C ₆₀ aryl phosphine group of the (preferably, C ₆ to C ₃₀ aryl phosphine group), C of ₆ to C ₆₀ aryl phosphine (Preferably a C ₆ to C ₃₀ arylphosphine oxide group) and a C ₆ to C ₆₀ arylamine group (preferably a C ₆ to C ₃₀ arylamine group). And when the substituent is plural, they are the same as or different from each other.

The compound of formula (1) may be represented by any one of the following formulas (4) to (7).

In the above formulas 4 to 7,

R ₁ to R ₄ , L ₁ , Ar _1, and Ar ₂ , a, b, and c are each as defined in Formula 1,

a 'is an integer of 0 to 4, b' is an integer of 0 to 2, and c 'is an integer of 0 to 3.

Examples of the compound represented by the formula (1) include compounds represented by the following formulas (8) to (11), but are not limited thereto.

In the general formulas (8) to (11)

R ₁ to R ₄ , L ₁ , Ar _1, and Ar ₂ , a, b, and c are each as defined in Formula 1,

a 'is an integer of 0 to 4, b' is an integer of 0 to 2, b '' is an integer of 0 to 1, and c 'is an integer of 0 to 3.

The compounds represented by formula (1) according to the present invention may be represented by the following compounds, but are not limited thereto.

As used herein, "unsubstituted alkyl" means a monovalent functional group obtained by removing a hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, iso Butyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

As used herein, "unsubstituted cycloalkyl" means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms (saturated cyclic hydrocarbon). Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

As used herein, "unsubstituted heterocycloalkyl" means a monovalent functional group obtained by removing a hydrogen atom from a non-aromatic hydrocarbon (saturated cyclic hydrocarbon) having 3 to 40 nuclear atoms, and at least one carbon , Preferably one to three carbons, is substituted with a heteroatom such as N, O or S. Non-limiting examples thereof include morpholine, piperazine, and the like.

As used herein, "unsubstituted aryl" means a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. At this time, the two or more rings may be attached to each other in a simple attached or condensed form. Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, and the like.

The "unsubstituted heteroaryl" used in the present invention is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, , One to three carbons are substituted with a heteroatom such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se). At this time, the heteroaryl may be attached in a form in which two or more rings are attached or condensed to each other, and may further include a condensed form with an aryl group. Non-limiting examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl and the like.

As used herein, "unsubstituted alkyloxy" means a monovalent functional group represented by RO-, wherein R is an alkyl having 1 to 40 carbon atoms, which may be linear, branched or cyclic ) Structure. Non-limiting examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.

As used herein, "unsubstituted aryloxy" means a monovalent functional group represented by R'O-, and R 'is aryl having 6 to 60 carbon atoms. Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like.

As used herein, the term "unsubstituted alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, "unsubstituted arylsilyl" means silyl substituted with aryl having 6 to 60 carbon atoms, Unsubstituted arylamine "refers to an amine substituted with aryl of 6 to 60 carbon atoms.

In the present invention, the term "unsubstituted alkylboron group" means a boron group substituted with alkyl having 1 to 40 carbon atoms, "unsubstituted arylboron group" means a boron group substituted with aryl having 6 to 60 carbon atoms, Unsubstituted arylphosphine group "means a phosphine group substituted with aryl having 1 to 60 carbon atoms, and the unsubstituted aryl phosphine oxide group means a phosphine oxide group substituted with aryl having 1 to 60 carbon atoms.

As used herein, "fused ring" means a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.

The compounds of formula 1 of the present invention can be synthesized according to the general synthetic methods ( Chem . Rev. , 60 : 313 (1960); J. Chem . SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995 ). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

On the other hand, the present invention provides an organic electroluminescent device comprising a compound represented by the above-mentioned formula (1) (preferably a compound represented by any one of the above-mentioned formulas (4) to (7)).

Specifically, the present invention includes a cathode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes the compound represented by Formula 1. At this time, the compounds may be used alone or in combination of two or more.

According to an embodiment of the present invention, the at least one organic material layer includes a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer and an electron injecting layer, and at least one organic material layer contains the compound, The hole transporting layer may contain the above compound. In particular, when the compound represented by Formula 1 is included in the organic electroluminescent device as a light emitting layer material, the luminous efficiency, brightness, power efficiency, thermal stability, and device lifetime of the organic electroluminescent device can be improved.

For example, the compound represented by Formula 1 may be a phosphorescent host, a fluorescent host, or a dopant material of the light emitting layer, and may preferably be a phosphorescent host of the light emitting layer.

According to another embodiment of the present invention, the at least one organic material layer includes a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer and an electron injecting layer, wherein at least one organic material layer, May include a compound represented by the above formula (1). Particularly, when the compound is used as a light-emitting auxiliary layer material of an organic electroluminescent device, the efficiency (luminous efficiency and power efficiency), lifetime, brightness and driving voltage of the organic electroluminescent device can be improved.

The structure of the organic electroluminescent device of the present invention is not particularly limited. For example, a structure in which an anode, one or more organic material layers and a cathode are sequentially laminated on a substrate, and an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic material layer .

According to an example, the organic electroluminescent device may have a structure in which an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially stacked on a substrate. Alternatively, a light-emitting auxiliary layer may be interposed between the hole transport layer and the light emitting layer. The electron injection layer may be located on the electron transport layer.

The organic electroluminescent device of the present invention may be formed by using a material known in the art (for example, a light emitting layer or a light emitting auxiliary layer) such that at least one of the one or more organic layers And forming an organic layer and an electrode using a method.

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.

Examples of substrates usable in the present invention include silicon wafers, quartz or glass plates, metal plates, plastic films and sheets, but are not limited thereto.

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 and polyaniline; Or 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; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The material used for the hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer is not particularly limited as long as it is a conventional material known in the art.

Hereinafter, the present invention will be described in detail with reference to the following examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

[ Preparation Example  One] Core1 Synthesis of

<Step 1> 5- chloro -2-nitro-5'-phenyl-1,1 ': 3', 1 "- 테 페렌 Synthesis of

4-chloro-2-iodo- 1-nitrobenzene 30g (105.84 mmol), under nitrogen gas stream, [1,1 ': 3', 1 '' - terphenyl] -5'-ylboronic acid 34.8g (127 mmol), K 2 43.88 g (317.52 mmol) of CO ₃ and 400 ml / 100 ml of 1,4-dioxane / H ₂ O were added and stirred. At 40 ℃ placed _{Pd (PPh 3) 4 3.7 g} (3.175 mmol), it was stirred under reflux at 110 ℃ for 12 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, and the organic layer was dried over MgSO ₄ and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and 5-chloro-2-nitro-5'-phenyl-1,1 ': 3', 1 "-terphenyl (32 g, yield 78% .

¹ H-NMR:? 7.32 (m, 2H), 7.53 (m, 4H), 7.78 (m, 5H), 8.08

<Step 2> 6- chloro -1,3- 피덴 -9H- carbazole Synthesis of

30 g (82.93 mmol) of 5-chloro-2-nitro-5'-phenyl-1,1 ': 3', 1 "-terphenyl synthesized in Step 1 under nitrogen flow, 43.5 g (165.86 mmol) of triphenylphosphine, , And 300 ml of 1,2-dichlorobenzene were added thereto, followed by reflux stirring at 180 ° C for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed by distillation, and an organic layer was extracted with dichloromethane. The extracted organic layer was dried with MgSO ₄ and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and 6-chloro-1,3-diphenyl-9H-carbazole (20 g, yield: 67%) was obtained by column chromatography.

¹ H-NMR:? 7.15 (m, 5H), 7.58 (m, 6H), 7.75 (m, 3H), 8.03

<Step 3> Of Core1  synthesis

The <Step 2> The 6-chloro-1,3-diphenyl- 9H-carbazole 20 g (56.52 mmol) synthesized in a nitrogen stream, Iodobenzene 13.8 g (67.82 mmol) , Cu powder 0.06 g (5.652 mmol), K 2 15.6 g (113 mmol) of CO ₃ and nitrobenzene (200 ml) were mixed and refluxed at 190 ° C for 12 hours.

After the reaction was terminated, the nitrobenzene 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 a compound Core1 (18 g, yield: 74%).

^{1 H-NMR: δ 7.02 (} d, 1H), 7.25 (m, 4H), 7.58 (m, 7H), 7.88 (m, 3H) 8.08 (s, 1H)

[ Preparation Example  2] Core2 Synthesis of

<Step 1> 5- chloro -2-nitro-5'-phenyl-1,1 ': 2', 1 "- 테 페렌 Synthesis of

[1,1 ': 4', 1 "-terphenyl] -2 (2'-tert-butylphenyl) -5'-ylboronic acid was used in place of [ 2-nitro-5'-phenyl-1,1 ': 2 (1) was obtained by following the procedure of <Step 1> of Preparation Example 1, except that 34.8 g ', 1' '- terphenyl (31 g, yield: 75%).

^{1 H-NMR: δ7.36 (m} , 7H), 7.88 (m, 5H), 8.25 (m, 2H), 8.52 (m, 2H)

<Step 2> 6- chloro -1,4- 피덴 -9H- carbazole Synthesis of

Chloro- 2-nitro-5'-phenyl-1,1 ': 3', 1 "-terphenyl used in Step 2 of Preparation Example 1 was used instead of 5-chloro- Step 2 of Preparation Example 1 was repeated, except that 30 g (82.93 mmol) of 2-nitro-5'-phenyl-1,1 ': 2', 1 " -chloro-1,4-diphenyl-9H-carbazole (19 g, yield 64%).

^{1 H-NMR: δ 7.12 (} m, 5H), 7.48 (m, 6H), 7.82 (m, 2H), 8.23 (m, 2H), 12.18 (s, 1H)

<Step 3> Core2  synthesis

Except that 20 g (56.52 mmol) of 6-chloro-1,4-diphenyl-9H-carbazole was used instead of the 6-chloro-1,3-diphenyl-9H-carbazole used in Step 3 of Preparation Example 1 , And Step 3 of Preparation Example 1 were carried out to obtain a compound Core2 (18 g, yield: 74%).

^{1 H-NMR: δ 7.02 (} d, 1H), 7.28 (m, 4H), 7.52 (m, 11H), 7.85 (m, 2H) 8.41 (d, 1H), 8.52 (d, 1H)

[ Preparation Example  3] Core3  synthesis

20 g (56.52 mmol) of 6-chloro-1,3-diphenyl-9H-carbazole, 8.27 g (67.82 mmol) of phenylboronic acid and 55.2 g (169.56 mmol) of Cs ₂ CO ₃ obtained in Step 2 of Preparation Example 1 2.7 g (5.65 mmol) of X-Phos and 1,4-dioxane / H ₂ O (400 ml / 100 ml) were added and stirred. 0.38 g (1.695 mmol) of Pd (oAc) ₂ was added thereto at 40 ° C, and the mixture was refluxed and stirred at 110 ° C for 12 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, and the organic layer was dried over MgSO ₄ and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and then subjected to column chromatography to obtain a compound Core 3 (16 g, yield: 71%).

^{1 H-NMR: δ 7.18 (} m, 4H), 7.50 (m, 7H), 7.82 (m, 6H), 7.92 (s, 1H), 8.08 (m, 2H), 12.25 (s, 1H)

[ Preparation Example  4] Core4  synthesis

20 g (56.52 mmol) of 6-chloro-1,4-diphenyl-9H-carbazole obtained in Step 2 of Preparation Example 2 was used instead of 6-chloro-1,3-diphenyl-9H- , Core 4 (15 g, yield: 67%) was obtained in the same manner as in Preparation Example 3.

^{1 H-NMR: δ 7.15 (} m, 4H), 7.47 (m, 7H), 7.81 (m, 5H), 7.92 (s, 1H), 8.03 (d, 1H), 8.26 (m, 2H), 12.18 ( s, 1 H)

[ Preparation Example  5] Core5  synthesis

<Step 1> 4- chloro -2-nitro-5'-phenyl-1,1 ': 3', 1 "- 테 페렌 Synthesis of

4-chloro-2-iodo- 1-nitrobenzene 30g (105.83 mmol), under nitrogen gas stream, [1,1 ': 3', 1 '' - terphenyl] -5'-ylboronic acid 34.8g (127 mmol), K 2 43.88 g (317.52 mmol) of CO ₃ and 1,4-dioxane / H ₂ O (400 ml / 100 ml) were added and stirred. At 40 ℃ placed _{Pd (PPh 3) 4 3.7 g} (3.175 mmol), it was stirred under reflux at 110 ℃ for 12 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, and the organic layer was dried over MgSO ₄ and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and 4-chloro-2-nitro-5'-phenyl-1,1 ': 3', 1 "-terphenyl (32 g, yield: 78%) was obtained by column chromatography .

¹ H-NMR:? 7.51 (m, 6H), 7.82 (m, 4H), 8.05

<Step 2> 7- chloro -1,3- 피덴 -9H- carbazole Synthesis of

Chloro- 2-nitro-5'-phenyl-1,1 ': 3', 1 "-terphenyl used in Step 2 of Preparation Example 1 was used instead of 5-chloro-2- Step 2 of Preparation Example 1 was repeated except that 30 g (82.93 mmol) of 2-nitro-5'-phenyl-1,1 ': 3', 1 " -chloro-1,3-diphenyl-9H-carbazole (20 g, yield 67%).

^{1 H-NMR: δ 6.98 (} d, 1H), 7.18 (m, 4H), 7.45 (m, 5H), 7.78 (m, 3H), 8.05 (m, 2H), 12.20 (s, 1H)

<Step 3> Core5  synthesis

Except that 20 g (56.52 mmol) of 7-chloro-1,3-diphenyl-9H-carbazole was used in place of 6-chloro-1,3-diphenyl-9H-carbazole used in Preparation Example 3 (16 g, yield: 71%) was obtained.

^{1 H-NMR: δ 7.2 (} m, 4H), 7.48 (m, 7H), 7.78 (m, 6H), 7.92 (d, 1H), 8.05 (s, 1H), 8.30 (d, 1H), 12.22 ( s, 1 H)

[ Preparation Example  6] Core6  synthesis

<Step 1> 1- chloro -3- 메틸oxy -9-phenyl-9H- carbazole  synthesis

Except that 20 g (86.33 mmol) of 1-chloro-3-methoxy-9H-carbazole was used in place of the 6-chloro-1,3-diphenyl-9H-carbazole used in Step 3 of Preparation Example 1 1-chloro-3-methoxy-9-phenyl-9H-carbazole (20 g, yield: 75%) was obtained in the same manner as in <Step 3> of Example 1.

^{1 H-NMR: δ 3.88 (} s, 3H), 6.75 (s, 1H), 7.22 (t, 1H), 7.45 (t, 1H) 7.68 (m, 6H), 8.02 (d, 1H), 8.58 (d , 1H)

&Lt; Step 2 > 3- 메틸oxy -1,9- 피덴 -9H- carbazole Synthesis of

20 g (64.98 mmol) of 1-chloro-3-methoxy-9-phenyl-9H-carbazole was used in place of 4-chloro-2-iodo-1-nitrobenzene used in <Step 1> , Step 1 of Preparation Example 1 was repeated except that 9.5 g (77.97 mmol) of phenyl boronic acid was used instead of 1 ': 3', 1 "-terphenyl] -5'-ylboronic acid 3-methoxy-1,9-diphenyl-9H-carbazole (16 g, yield: 70%).

^{1 H-NMR: δ 3.82 (} s, 3H), 7.16 (m, 5H), 7.62 (m, 8H), 7.85 (s, 1H), 7.92 (d, 1H), 8.57 (d, 1H)

&Lt; Step 3 > 피덴 -9H- carbazole -3- ol  synthesis

16 g (45.78 mmol) of 3-methoxy-1,9-diphenyl-9H-carbazole obtained in the above Step 2 was added to 400 mL of 48% aqueous hydrobromic acid under a nitrogen stream and stirred at 120 ° C for 5 hours. The reaction mixture was cooled to 40 ° C, and 1 L of water was added thereto, followed by neutralization with sodium bicarbonate. Thereafter, the resulting solid was filtered, dried and then purified by column chromatography to obtain 1,9-diphenyl-9H-carbazol-3-ol (6 g, yield: 40%).

¹ H-NMR:? 7.18 (m, 5H), 7.51 (m, 9H), 8.02 (d,

<Step 4> Synthesis of Core 6

6 g (17.88 mmol) of 1,9-diphenyl-9H-carbazol-3-ol, 2.5 g (8.94 mmol) of trifluoromethanesulfonic anhydride and 10 g (17.88 mmol) of pyridine obtained in the above Step 3 were dissolved in a 100 mL Dichloromethane and stirred at 0 ° C for 1 hour. After completion of the reaction, the organic layer was extracted with dichloromethane, and the organic layer was dried over MgSO ₄ and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and then Core 6 (5.8 g, yield: 69%) was obtained by column chromatography.

^{1 H-NMR: δ 7.15 (} m, 5H), 7.48 (m, 9H), 7.94 (m, 2H), 8.15 (m, 3H) 8.62 (d, 1H)

[ Synthetic example  1] Compound Inv  Synthesis of 1

Under nitrogen atmosphere, 3.0 g (6.97 mmol) of the compound Core1 synthesized in Preparation Example 1 and 2.77 g of N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren- (7.66 mmol), Pd (OAc ) 2 0.047 g (0.209mmol), NaO (t-bu) 1.34 g (13.94 mmol), P (t-bu) 3 0.14 g (0.697 mmol) and Toluene (80 ml) to After mixing, the mixture was stirred at 110 DEG C for 12 hours.

After the reaction was completed, the organic layer was extracted with ethyl acetate. The organic layer was dried over MgSO ₄ and purified by column chromatography to obtain the desired compound Inv1 (2.8 g, yield: 53%).

GC-Mass (calculated: 754.98 g / mol, measured: 754 g / mol)

[ Synthetic example  2] Compound Inv  Synthesis of 13

([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine instead of N - yl) amine (2.4 g, 7.66 mmol) was used as a starting material, the target compound Inv 13 (2.6 g, yield: 52%) was obtained

GC-Mass (calculated: 714.91 g / mol, measured: 714 g / mol)

[ Synthetic example  3] Compound Inv  Synthesis of 37

(9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl (4-methylphenyl) 3.38 g (7.66 mmol) of boronic acid, 2.89 g (20.91 mmol) of K ₂ CO ₃ and 100 ml / 250 ml of 1,4-dioxane / H ₂ O were added and stirred. 0.24 g (0.209 mmol) of Pd (PPh ₃ ) ₄ was added at 40 ° C, and the mixture was refluxed and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane. The organic layer was dried over MgSO ₄ and filtered under reduced pressure. The filtrated organic layer was distilled under reduced pressure, and the desired compound Inv37 (3.5 g, yield: 60%) was obtained by column chromatography.

GC-Mass (theory: 831.08 g / mol, measurement: 831 g / mol)

[ Synthetic example  4] Compound Inv  Synthesis of 49

Instead of (4- (di ((1,1'-biphenyl) -4-yl (9,9-dimethyl-9H- The same procedure as in Synthesis Example 3 was carried out except that 3.38 g (7.66 mmol) of [1,1'-biphenyl] -4-yl) amino) , Yield: 65%).

GC-Mass (theory: 791.01 g / mol, measured: 791 g / mol)

[ Synthetic example  5] Compound Inv  Synthesis of 70

Instead of (4- (bis (4-methylpiperazin-1-yl) amino) phenyl) boronic acid used in Synthesis Example 3 instead of 4- The same procedure as in Synthesis Example 3 was carried out except that 4.0 g (7.66 mmol) of 9,9-dimethyl-9H-fluoren-2-yl) amino) g, yield: 63%).

GC-Mass (calculated: 871.14 g / mol, measured: 871 g / mol)

[ Synthetic example  6] compound Inv  Synthesis of 87

(4- (diphenylamino) phenyl) boronic acid instead of (4 - ([1,1'-biphenyl] -4-yl phenyl) boronic acid (2.21 g, 7.66 mmol) was used in place of the compound obtained in Synthesis Example 3 to obtain Inv 87 (2.8 g, yield 62%) as a target compound.

GC-Mass (theory: 638.8 g / mol, measured: 638 g / mol)

[ Synthetic example  7] Compound Inv  Synthesis of 89

(4 '- ([(1, 1'-biphenyl) -4-yl (9,9- (9,9-dimethyl-9H-fluoren-2-yl) amino] - [1,1'-biphenyl] -4-yl) boronic acid, 4.27 g (7.66 mmol) (Inv 89) (4.0 g, yield: 63%) was obtained by carrying out the same procedure as in Synthesis Example 3, except that

GC-Mass (907.17 g / mol, measured: 907 g / mol)

[ Synthetic example  8] compound Inv 91 of  synthesis

(3 '- ([(1, 1'-biphenyl) -4-yl (9,9- (9,9-dimethyl-9H-fluoren-2-yl) amino] - [1,1'-biphenyl] -4-yl) boronic acid, 4.27 g (7.66 mmol) , The procedure of Synthesis Example 3 was repeated to obtain the target compound Inv91 (4.2 g, yield: 66%).

GC-Mass (907.17 g / mol, measured: 907 g / mol)

[ Synthetic example  9] compound Inv  Synthesis of 93

The same procedure as in Synthesis Example 1 was carried out, except that 3.0 g (6.97 mmol) of the compound Core2 synthesized in Preparation Example 2 was used instead of the compound Core1 used in Synthesis Example 1, to obtain the desired compound Inv 93 (2.9 g, yield : 55%).

GC-Mass (theory: 822.87 g / mol, measured: 822 g / mol)

[ Synthetic example  10] compound Inv  Synthesis of 105

Synthesis Example 2 The same procedure as in Synthesis Example 2 was carried out except that 3.0 g (6.97 mmol) of the compound Core2 synthesized in Preparation Example 2 was used in place of the used compound Core1 to obtain the desired compound Inv 105 (2.7 g, yield: 54%).

GC-Mass (calculated: 714.91 g / mol, measured: 714 g / mol)

[ Synthetic example  11] compound Inv  Synthesis of 129

The procedure of Synthesis Example 3 was repeated except that 3.0 g (6.97 mmol) of the compound Core2 in Preparation Example 2 was used instead of the compound Core1 used in Synthesis Example 3 to obtain the desired compound Inv 129 (3.3 g, yield: 60 %).

GC-Mass (calculated: 831.09 g / mol, measured: 831 g / mol)

[ Synthetic example  12] compound Inv  Synthesis of 141

In the same manner as in Synthesis Example 4 except that 3.0 g (6.97 mmol) of the compound Core2 in Preparation Example 2 was used instead of the compound Core1 used in Synthesis Example 4, Inv 141 (2.9 g, yield: 55 %).

GC-Mass (theory: 791.01 g / mol, measured: 791 g / mol)

[ Synthetic example  13] Compound Inv  Synthesis of 183

The procedure of Synthetic Example 8 was repeated, except that 3.0 g (6.97 mmol) of the compound Core2 in Preparation Example 2 was used instead of the compound Core1 used in Synthesis Example 8, to obtain the desired compound Inv 183 (3.9 g, yield: 61 %).

GC-Mass (907.17 g / mol, measured: 907 g / mol)

[ Synthetic example  14] Compound Inv  Synthesis of 221

(3.0 g, 7.58 mmol) and N - ([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H-fluorene -2-amine, 0.048 g (0.758 mmol) of Cu powder, K ₂ CO ₃ 2.09 g (15.16 mmol) and nitrobenzene (80 ml) were mixed and refluxed at 190 캜 for 12 hours.

After the reaction was terminated, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and then the 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, Inv 221 (3.8 g, yield 60%).

GC-Mass (theory: 831.08 g / mol, measurement: 831 g / mol)

[ Synthetic example  15] Compound Inv  Synthesis of 227

N - ([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H- -4-yl) -N- (4-bromophenyl) -9,9-diphenyl-9H-fluoren-2-amine (5.83 g, 9.1 mmol) The target compound Inv 227 (4.4 g, yield 61%) was obtained.

GC-Mass (calculated: 955.22 g / mol, measured: 955 g / mol)

[ Synthetic example  16] compound Inv  Synthesis of 233

Instead of N - ([1, 1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H- fluoren- , 4'-biphenyl] -4-yl) -N- (4-bromophenyl) - [1,1'-biphenyl] -4-amine The same procedure was followed to obtain the desired compound Inv 233 (4.0 g, yield 66%).

GC-Mass (theory: 791.01 g / mol, measured: 791 g / mol)

[ Synthetic example  17] Compound Inv  Synthesis of 254

(4-bromophenyl) -9,9-dimethyl-9H-fluoren-2-amine instead of the N - ([1,1'- biphenyl] -4-yl) -N- except that 5.0 g (9.1 mmol) of bromophenyl-N- (9,9-dimethyl-9H-fluoren-2-yl) -9,9-dimethyl-9H- 14, the target compound Inv 254 (4.1 g, yield 62%) was obtained.

GC-Mass (calculated: 871.14 g / mol, measured: 871 g / mol)

[ Synthetic example  18] compound Inv  Synthesis of 273

Instead of N - ([1, 1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H- fluoren- -4'-biphenyl] -4-yl) -N- (4'-bromo- [1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H- 9.1 mmol), the target compound Inv 273 (4.5 g, yield 65%) was obtained by carrying out the same procedure as in Synthesis Example 14.

GC-Mass (907.17 g / mol, measured: 907 g / mol)

[ Synthetic example  19] Compound Inv  Synthesis of 313

Inv 313 (4.3 g, yield 68%) was obtained in the same manner as in Synthesis Example 14, except that 3.0 g (7.58 mmol) of Core 4 obtained in Preparation Example 4 was used instead of Core 3 used in Synthesis Example 14. &Lt; / RTI &gt;

GC-Mass (theory: 831.08 g / mol, measurement: 831 g / mol)

[ Synthetic example  20] compound Inv  Synthesis of 319

Inv 319 (4.8 g, yield 66%) was obtained by carrying out the same procedure as in Synthesis Example 15, except that 3.0 g (7.58 mmol) of Core 4 obtained in Preparation Example 4 was used instead of Core 3 used in Synthesis Example 15 .

GC-Mass (calculated: 955.22 g / mol, measured: 955 g / mol)

[ Synthetic example  21] Inv  Synthesis of 325

Inv 325 (3.9 g, yield 65%) was obtained by carrying out the same procedure as in Synthesis Example 16, except that 3.0 g (7.58 mmol) of Core 4 obtained in Preparation Example 4 was used instead of Core 3 used in Synthesis Example 16. ).

GC-Mass (theory: 791.01 g / mol, measured: 791 g / mol)

[ Synthetic example  22] compound Inv  346

Inv 346 (4.2 g, yield 63%) was obtained in the same manner as in Preparation Example 17, except that 3.0 g (7.58 mmol) of Core 4 obtained in Preparation Example 4 was used in place of Core 3 used in Preparation Example 17. &Lt; / RTI &gt;

GC-Mass (calculated: 871.14 g / mol, measured: 871 g / mol)

[ Synthetic example  23] Compound Inv  Synthesis of 365

Inv 365 (4.4 g, yield 64%) was obtained in the same manner as in Synthesis Example 18, except that 3.0 g (7.58 mmol) of Core 4 obtained in Preparation Example 4 was used instead of Core 3 used in Synthesis Example 18. .

GC-Mass (907.17 g / mol, measured: 907 g / mol)

[ Synthetic example  24] Compound Inv  Synthesis of 405

Inv 405 (4.1 g, yield 65%) was obtained in the same manner as in Synthesis Example 14, except that 3.0 g (7.58 mmol) of Core 5 obtained in Preparation Example 5 was used instead of Core 3 used in Synthesis Example 14. .

GC-Mass (theory: 831.08 g / mol, measurement: 831 g / mol)

[ Synthetic example  25] Compound Inv  Synthesis of 411

Inv 411 (4.5 g, yield 62%) was obtained in the same manner as in Synthesis Example 15, except that 3.0 g (7.58 mmol) of Core 5 obtained in Preparation Example 5 was used instead of Core 3 used in Synthesis Example 15. .

GC-Mass (calculated: 955.22 g / mol, measured: 955 g / mol)

[ Synthetic example  26] compound Inv  Synthesis of 417

Inv 417 (3.9 g, yield 65%) was obtained in the same manner as in Synthesis Example 16, except that 3.0 g (7.58 mmol) of Core 5 obtained in Preparation Example 5 was used instead of Core 3 used in Synthesis Example 16. &Lt; / RTI &gt;

GC-Mass (theory: 791.01 g / mol, measured: 791 g / mol)

[ Synthetic example  27] Compound Inv  Synthesis of 457

Inv 457 (4.3 g, yield 63%) was obtained by carrying out the same procedure as in Synthesis Example 18, except that 3.0 g (7.58 mmol) of Core 5 obtained in Preparation Example 5 was used instead of Core 3 used in Synthesis Example 18, &Lt; / RTI &gt;

GC-Mass (907.17 g / mol, measured: 907 g / mol)

[ Synthetic example  28] Compound Inv  Synthesis of 459

Except that Core5 3.0 g (7.58 mmol) obtained in Preparation Example 5 was used in place of Core 3 used in Synthesis Example 14 and N - ([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9 4-yl) -N- (4'-bromo- [1,1'-biphenyl] -3-yl ) The title compound, Inv 459 (4.2 g, yield 61%) was obtained by following the same procedure as in Synthesis Example 14, except for using 5.38 g (9.1 mmol) of 9,9-dimethyl-9H- ).

GC-Mass (907.17 g / mol, measured: 907 g / mol)

[ Synthetic example  29] Compound Inv 588  synthesis

The procedure of Synthesis Example 3 was repeated except that 3 g (6.41 mmol) of Core 6 synthesized in <Step 4> of Preparation Example 6 was used instead of Core 1 used in Synthesis Example 3 to obtain the target compound Inv 588 (3.3 g, yield 68%) was obtained

GC-Mass (calculated: 754.98 g / mol, measured: 754 g / mol)

[ Synthetic example  30] Compound Inv 600  synthesis

The same procedure as in Synthesis Example 4 was carried out except that 3 g (6.41 mmol) of Core 6 synthesized in <Step 4> of Preparation Example 6 was used instead of Core 1 used in Synthesis Example 4 to obtain the target compound Inv 600 (3.1 g, yield 68%) was obtained

GC-Mass (calculated: 714.91 g / mol, measured: 714 g / mol)

[ Synthetic example  31] Compound Inv  Synthesis of 638

Except that 3 g (6.41 mmol) of Core 6 synthesized in <Step 4> of Preparation Example 6 was used instead of Core1 used in Synthesis Example 6, the target compound Inv 638 ( 2.5 g, yield 70%) was obtained

GC-Mass (calculated: 562.72 g / mol, measured: 562 g / mol)

[ Synthetic example  32] compound Inv 680  synthesis

The procedure of Synthesis Example 3 was repeated except that 3.0 g (8.47 mmol) of 1-chloro-3,9-diphenyl-9H-carbazole was used in place of Core 1 used in Synthesis Example 3 to obtain the target compound Inv 680 4.0 g, yield: 62%) was obtained

GC-Mass (calculated: 754.98 g / mol, measured: 754 g / mol)

[ Synthetic example  33] Compound Inv  Synthesis of 692

Instead of (4- (di ((1,1'-biphenyl) -4-yl (9,9-dimethyl-9H-fluoren- The same procedure as in Synthesis Example 32 was carried out, except that 4.54 g (10.16 mmol) of [1,1'-biphenyl] -4-yl) amino) , Yield: 63%).

GC-Mass (calculated: 714.91 g / mol, measured: 714 g / mol)

[ Synthetic example  34] Compound C- 1 of  synthesis

<Step 1> Synthesis of 1-phenyl-9H- carbazole Synthesis of

10 g (49.59 mmol) of 1-chloro-9H-carbazole was used in place of Core1 used in Synthesis Example 3, and (4 - ([1,1'-biphenyl] -4-yl Phenyl-9H-carbazole (8.5 g, yield: 97%) was obtained in the same manner as in Synthesis Example 3, except that 7.25 g (59.5 mmol) of phenyl boronic acid was used in place of 2- : 70%).

^{1 H-NMR: δ 7.22 (} m, 3H), 7.52 (m, 2H), 7.67 (d, 1H), 8.12 (d, 1H), 8.22 (d, 1H), 8.35 (d, 1H), 12.15 ( s, 1 H)

<Step 2> Synthesis of Compound C-1

The procedure of Synthesis Example 14 was repeated except that 8.5 g (34.93 mmol) of 1-phenyl-9H-carbazole synthesized in the above Step 1 was used instead of Core 3 used in Synthesis Example 14 to obtain the target compound C -1 (16 g, yield: 67%).

GC-Mass (theory: 678.88 g / mol, measured: 678 g / mol)

[ Synthetic example  35] Compound C- 2 of  synthesis

<Step 1> 1,4- 피덴 -2,3,4,9- tetrahydro -1H- carbazole Synthesis of

50 g (199.72 mmol) of 2,5-diphenylcyclohexan-1-one, 29 g (199.72 mmol) of phenylhydrazine hydrochloride and 500 ml of acetic acid were placed under a nitrogen stream and refluxed at 120 ° C for 12 hours. After completion of the reaction, acetic acid was removed, and the organic layer was extracted with sodium bicarbonate and dichloromethane. The organic layer was dried with MgSO ₄ and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and 1,4-diphenyl-2,3,4,9-tetrahydro-1H-carbazole (43 g, yield 66%) was obtained by column chromatography.

^{1 H-NMR: δ 1.96 (} m, 2H), 4.02 (m, 2H), 6.83 (m, 2H), 7.29 (m, 4H), 7.75 (d, 1H), 8.05 (d, 1H), 12.12 ( s, 1 H)

&Lt; Step 2 > 피덴 -9H- carbazole Synthesis of

43 g (133.12 mmol) of 1,4-diphenyl-2,3,4,9-tetrahydro-1H-carbazole obtained in the above Step 1 and 300 ml of benzene were placed in a nitrogen gas stream, g (264.24 mmol), and the mixture was stirred for 1 hour. After completion of the reaction, the mixture was filtered through Silicagel and Celite, benzene was removed, and organic layer was extracted with dichloromethane. The extracted organic layer was dried with MgSO ₄ and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and 1,4-diphenyl-9H-carbazole (29 g, yield: 70%) was obtained by column chromatography.

¹ H-NMR:? 7.22 (m, 5H), 7.42 (m, 4H), 7.68 (d,

<Step 3> Synthesis of Compound C-2

The procedure of Synthesis Example 14 was repeated except that 10 g (31.3 mmol) of 1,4-diphenyl-9H-carbazole was used in Step 2 instead of Core 3 used in Synthesis Example 14, 2 (15.8 g, yield 67%).

GC-Mass (calculated: 754.98 g / mol, measured: 754 g / mol)

[ Example  1] - Manufacture of organic EL device

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

(60 nm) / compound Inv 1 (80 nm) / [DS-H522 + 5% DS-501] (30 nm) / BCP (10 nm) synthesized in Synthesis Example 1 on the ITO transparent electrode prepared above, / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm).

DS-H522 and DS-501 used in the above are products of Doosan Electronics BG Co., Ltd. The structures of m-MTDATA and BCP are as follows.

[ Example  2 ~ 35] - Manufacture of organic EL device

An organic EL device was manufactured in the same manner as in Example 1 except that the compound described in Table 1 was used instead of the compound Inv 1 used as a hole transporting layer material in the formation of the hole transport layer in Example 1.

[ Comparative Example  1] - Fabrication of organic EL device

An organic EL device was prepared in the same manner as in Example 1, except that NPB was used as the hole transport layer material instead of the compound Inv 1 used as the hole transport layer material in forming the hole transport layer in Example 1. The structure of the NPB used here is as follows.

[ Evaluation example  One]

The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for the organic EL devices manufactured in Examples 1 to 35 and Comparative Example 1, respectively, and the results are shown in Table 1 below.

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 1 Compound Inv 1 4.2 21.2 Example 2 Compound Inv 13 4.3 20.1 Example 3 Compound Inv 37 4.1 23.3 Example 4 Compound Inv 49 4.0 22.6 Example 5 Compound Inv 70 4.5 19.5 Example 6 Compound Inv 87 4.7 20.1 Example 7 Compound Inv 89 4.3 21.6 Example 8 Compound Inv 91 4.5 20.5 Example 9 Compound Inv 93 4.9 20.0 Example 10 Compound Inv 105 5.0 19.6 Example 11 Compound Inv 129 5.2 19.8 Example 12 Compound Inv 141 5.1 18.6 Example 13 Compound Inv 183 5.0 20.0 Example 14 Compound Inv 221 4.3 22.5 Example 15 Compound Inv 227 4.5 21.2 Example 16 Compound Inv 233 4.4 22.3 Example 17 Compound Inv 254 4.9 18.5 Example 18 Compound Inv 273 4.8 19.9 Example 19 Compound Inv 313 5.0 19.8 Example 20 Compound Inv 319 4.9 19.2 Example 21 Compound Inv 325 4.8 20.0 Example 22 Compound Inv 346 4.9 19.1 Example 23 Compound Inv 365 5.1 18.2 Example 24 Compound Inv 405 4.2 22.5 Example 25 Compound Inv 411 4.3 22.3 Example 26 Compound Inv 417 4.6 21.4 Example 27 Compound Inv 457 4.8 21.6 Example 28 Compound Inv 459 4.2 22.5 Example 29 Compound Inv 346 4.5 21.6 Example 30 Compound Inv 365 4.8 22.3 Example 31 Compound Inv 405 4.2 22.1 Example 32 Compound Inv 411 4.3 21.8 Example 33 Compound Inv 417 4.6 21.7 Example 34 Compound C-1 5.2 18.5 Example 35 Compound C-2 5.1 18.2 Comparative Example 1 NPB 5.5 16.5

As shown in Table 1 above, the organic EL devices (organic EL devices of Examples 1 to 35) using the compounds (Inv 1 to Inv 417, C-1 to C-2) It was found that the current efficiency and the driving voltage were superior to those of the organic EL device using NPB (organic EL device of Comparative Example 1).

Further, the organic EL device of Example 14, in which the compound Inv 221 in which the phenyl group was introduced at positions 1, 3 and 6 of the carbazole, was used as the hole transport layer, was obtained by using Compound C-1 in which phenyl group was introduced at position 1 of carbazole It was found that the organic EL device of the present invention exhibited better current efficiency and driving voltage than the organic EL devices of Examples 34 to 35, in which the compound C-2 in which the phenyl group was introduced at positions 1 and 4 of carbazole was used as the hole transport layer.

[ Example  36] - green organic Field  Manufacturing of light emitting device

Inv 1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was prepared as follows.

Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. 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 the substrate was transferred to a vacuum evaporator.

(60 nm) / TCTA (80 nm) / Inv 1 (40 nm) / CBP + 10% Ir (ppy) ₃ (30 nm) / BCP (10 nm) on the ITO transparent electrode prepared above, Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

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

[ Example  37 ~ 63] - Green organic Field  Manufacturing of light emitting device

A green organic EL device was produced in the same manner as in Example 36 except that the compound shown in the following Table 2 was used instead of the compound Inv 1 used as the luminescent auxiliary layer material in the luminescent auxiliary layer in Example 36 Respectively.

[ Comparative Example  2] - green organic Field  Manufacturing of light emitting device

A green organic electroluminescent device was fabricated in the same manner as in Example 36 except that the compound Inv 1 used in Example 36 was not used.

[ Evaluation example  2]

The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 36 to 63 and Comparative Example 2, respectively, and the results are shown in Table 2 below .

Sample The light- The driving voltage (V) Current efficiency (cd / A) Example 36 Compound Inv 1 6.71 41.9 Example 37 Compound Inv 13 6.85 42.2 Example 38 Compound Inv 37 6.73 43.1 Example 39 Compound Inv 49 6.81 42.4 Example 40 Compound Inv 70 6.81 42.4 Example 41 Compound Inv 87 6.92 42.5 Example 42 Compound Inv 89 6.95 42.1 Example 43 Compound Inv 91 6.78 41.8 Example 44 Compound Inv 93 6.90 42.4 Example 45 Compound Inv 105 6.75 41.9 Example 46 Compound Inv 129 6.72 42.8 Example 47 Compound Inv 141 6.65 42.2 Example 48 Compound Inv 183 6.70 42.5 Example 49 Compound Inv 221 6.90 42.8 Example 50 Compound Inv 227 6.81 42.1 Example 51 Compound Inv 233 6.71 40.3 Example 52 Compound Inv 254 6.73 41.5 Example 53 Compound Inv 273 6.65 42.2 Example 54 Compound Inv 313 6.72 42.5 Example 55 Compound Inv 319 6.62 42.5 Example 56 Compound Inv 325 6.60 41.6 Example 57 Compound Inv 346 6.64 42.4 Example 58 Compound Inv 365 6.75 40.5 Example 59 Compound Inv 405 6.91 42.8 Example 60 Compound Inv 411 6.83 42.1 Example 61 Compound Inv 417 6.85 42.7 Example 62 Compound Inv 457 6.84 40.8 Example 63 Compound Inv 459 6.82 41.9 Comparative Example 2 - 6.98 36.5

As shown in Table 2 above, the green organic electroluminescent devices (the green organic electroluminescent devices of Examples 36 to 63) using the compound represented by Formula 1 according to the present invention as the light-emitting auxiliary layer material, It was found that the driving voltage was similar to that of the green organic electroluminescent device (organic electroluminescent device of Comparative Example 2) using only CBP as the light emitting layer material, but the luminous efficiency was improved.

[ Example  64] - Red organic Field  Manufacturing of light emitting device

Compound Inv 1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a method known in common, and then a red organic electroluminescent device was fabricated according to the following procedure.

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

(60 nm) / TCTA (80 nm) / Compound Inv 1 (40 nm) / CBP + 10% (piq) ₂ Ir (acac) (30 nm) / BCP 10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) were laminated in this order to prepare a red organic electroluminescent device.

The structures of m-MTDATA, TCTA, (piq) ₂ Ir (acac) and BCP used herein are as follows.

[ Example  65 ~ 91] - Red organic Field  Manufacturing of light emitting device

A red organic EL device was manufactured in the same manner as in Example 64 except that the compound described in the following Table 3 was used instead of the compound Inv 1 used as the luminescent auxiliary layer material in forming the luminescent auxiliary layer in Example 64 Respectively.

[ Comparative Example  3] - Red organic Field  Fabrication of light emitting device

A red organic electroluminescent device was manufactured in the same manner as in Example 64 except that Inv-1 was not used in Example 64. [

[ Evaluation example  3]

The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 64 to 91 and Comparative Example 3, respectively, and the results are shown in Table 2 below .

Sample The light- The driving voltage (V) Current efficiency (cd / A) Example 64 Compound Inv 1 5.25 10.9 Example 65 Compound Inv 13 5.34 10.8 Example 66 Compound Inv 37 5.42 11.3 Example 67 Compound Inv 49 5.38 10.4 Example 68 Compound Inv 70 5.30 11.0 Example 69 Compound Inv 87 5.64 9.2 Example 70 Compound Inv 89 5.32 10.8 Example 71 Compound Inv 91 5.48 11.4 Example 72 Compound Inv 93 5.36 12.2 Example 73 Compound Inv 105 5.43 10.1 Example 74 Compound Inv 129 5.38 12.2 Example 75 Compound Inv 141 5.52 11.6 Example 76 Compound Inv 183 5.29 10.4 Example 77 Compound Inv 221 5.30 11.7 Example 78 Compound Inv 227 5.13 10.9 Example 79 Compound Inv 233 5.37 10.2 Example 80 Compound Inv 254 5.34 12.0 Example 81 Compound Inv 273 5.26 10.3 Example 82 Compound Inv 313 5.29 11.2 Example 83 Compound Inv 319 5.32 10.8 Example 84 Compound Inv 325 5.34 9.8 Example 85 Compound Inv 346 5.18 10.2 Example 86 Compound Inv 365 5.33 10.6 Example 87 Compound Inv 405 5.25 12.5 Example 88 Compound Inv 411 5.32 10.3 Example 89 Compound Inv 417 5.42 10.9 Example 90 Compound Inv 457 5.30 9.8 Example 91 Compound Inv 459 5.35 11.2 Comparative Example 3 - 5.82 7.8

As shown in the above Table 3, the red organic electroluminescent devices (red organic electroluminescent devices of Examples 64 to 91) using the compound represented by Formula 1 according to the present invention as the light emitting auxiliary layer material, Compared with the red organic electroluminescent device (organic electroluminescent device of Comparative Example 3) using only CBP as the material of the light emitting layer, the driving voltage was similar but the luminous efficiency was improved.

[ Example  92] - blue organic Field  Manufacturing of light emitting device

The compound Inv 1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a red organic electroluminescent device was fabricated according to the following procedure.

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

(15 nm) / ADN + 5% DS-405 (Doosan) (30 nm) / BCP (compound semiconductor)) on the ITO transparent electrode prepared as above. (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) were laminated in this order to prepare a blue organic electroluminescent device.

The structures of NPB, ADN and BCP used at this time are as follows.

[ Example  93 ~ 119] - Blue organic Field  Manufacturing of light emitting device

A blue organic EL device was manufactured in the same manner as in Example 92 except that the compound shown in the following Table 4 was used instead of the compound Inv 1 used as the luminescent auxiliary layer material in the formation of the luminescent auxiliary layer in Example 92 Respectively.

[ Comparative Example  4] - blue organic Field  Fabrication of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 92 except that the compound Inv-1 used in Example 92 was not used.

[ Evaluation example  4]

The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for the blue organic electroluminescent devices fabricated in Examples 92 to 119 and Comparative Example 4, respectively, and the results are shown in Table 4 below.

Sample The light- The driving voltage (V) Current efficiency (cd / A) Example 92 Compound Inv 1 5.62 5.9 Example 93 Compound Inv 13 5.71 6.2 Example 94 Compound Inv 37 5.68 6.5 Example 95 Compound Inv 49 5.72 6.3 Example 96 Compound Inv 70 5.63 5.4 Example 97 Compound Inv 87 5.72 6.1 Example 98 Compound Inv 89 5.60 6.4 Example 99 Compound Inv 91 5.81 5.3 Example 100 Compound Inv 93 5.48 6.8 Example 101 Compound Inv 105 5.62 6.3 Example 102 Compound Inv 129 5.64 5.9 Example 103 Compound Inv 141 5.58 6.5 Example 104 Compound Inv 183 5.61 5.8 Example 105 Compound Inv 221 5.39 6.3 Example 106 Compound Inv 227 5.61 5.4 Example 107 Compound Inv 233 5.52 6.5 Example 108 Compound Inv 254 5.64 6.6 Example 109 Compound Inv 273 5.45 6.8 Example 110 Compound Inv 313 5.67 5.3 Example 111 Compound Inv 319 5.83 6.4 Example 112 Compound Inv 325 5.68 7.2 Example 113 Synthesis of Compound Inv 346 5.62 6.3 Example 114 Compound Inv 365 5.71 6.5 Example 115 Compound Inv 405 5.60 6.6 Example 116 Compound Inv 411 5.43 5.8 Example 117 Compound Inv 417 5.66 5.2 Example 118 Compound Inv 457 5.64 6.3 Example 119 Compound Inv 459 5.58 5.2 Comparative Example 4 - 5.6 4.8

As shown in Table 4, the blue organic electroluminescent devices (blue organic electroluminescent devices of Examples 92 to 119) using the compound represented by Formula 1 according to the present invention as the luminescent auxiliary layer material, It was found that the driving voltage was similar to that of the blue organic electroluminescent element including only the light emitting layer of ADN (organic electroluminescent element of Comparative Example 4), but the luminous efficiency was improved.

Claims (9)

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

(In the formula 1,
a is an integer from 0 to 5;
b is an integer from 0 to 3;
c is an integer from 0 to 4;
R ₁ to R ₄ are the same or different and are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms , A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 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 ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C of ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine An oxy group and an arylamine group of C ₆ to C ₆₀ , or may combine with adjacent substituents to form a condensed aromatic ring or a condensed heteroaromatic ring;
Provided that at least one of R ₁ to R ₄ is a substituent represented by the following formula (2);
(2)

* Is a moiety in which at least one of R ₁ to R ₄ is bonded;
L ₁ is selected from the group consisting of a single bond, a C ₆ to C ₆₀ arylene group and a heteroarylene group having 5 to 60 nuclear atoms;
Ar ₁ and Ar ₂ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms and a C ₆ to C ₆₀ And Ar ₁ and Ar ₂ may be bonded to each other to form a ring,
Alkyl group of Ar ₁ to Ar _2, an aryl group, a heteroaryl group and an arylamine group, R ₁ to the alkyl group of R _4, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkyl silyl group, aryl silyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group, an arylamine group, and L ₁ in the arylene group, heteroarylene group is deuterium, halogen, cyano, C ₁ ~ C _A C ₃ to C ₄₀ cycloalkyl group, a heterocyclic alkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ An alkyloxyl group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine value as pingi, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ at least one selected from the group consisting of aryl amine group of C ₆₀ Substituted or unsubstituted, and, if the beach, where the substituent of the plurality, all of which are the same or different from each other). The method according to claim 1,
R ₁ to R ₄ are the same or different and are each independently selected from the group consisting of C ₆ to C ₆₀ aryl groups, heteroaryl groups having 5 to 60 nuclear atoms, and C ₆ to C ₆₀ arylamine groups,
The aryl group, heteroaryl group and arylamine group of R ₁ to R ₄ are independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, heterocyclic An alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 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 ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ aryl phosphine of C ₆₀ pin oxide groups and C ₆ ~ C is substituted by a substituent at least one selected from the group consisting of ₆₀ with an aryl amine or is unsubstituted, wherein when the substituent is plural, they are the same or different and the compound is characterized by one another. The method according to claim 1,
Wherein the substituent represented by Formula 2 is a substituent represented by Formula 3:
(3)

(3)
L ₁ , Ar ₁ and Ar ₂ are as defined in claim 1,
Z ₂ is a single bond or is selected from the group consisting of O, S, and N (R ₅ )
R ₅ is hydrogen, deuterium _{(D), C 1 ~ C} 40 alkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atoms, a heteroaryl group of from 5 to 60, and C ₆ ~ from the group consisting of an aryl amine of the C ₆₀ of the Selected or may combine with adjacent substituents to form a condensed aromatic ring or a condensed heteroaromatic ring;
The aryl, heteroaryl and arylamine groups of R ₅ are each independently selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyl A silyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ aryl A phosphine oxide group and an arylamine group of C ₆ to C ₆₀ , provided that when the substituent is plural, they are the same as or different from each other). The method according to claim 1,
A compound represented by any one of the following formulas (4) to (7):
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

(In the above formulas 4 to 7,
R ₁ to R ₄ , L ₁ , Ar ₁ and Ar ₂ , a, b and c are each as defined in claim 1,
a 'is an integer of 0 to 4, b' is an integer of 0 to 2, and c 'is an integer of 0 to 3. The method according to claim 1,
A compound represented by any one of the following formulas (8) to (11):
[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

(In the above formulas 8 to 11,
R ₁ to R ₄ , L ₁ , Ar ₁ and Ar ₂ , a, b and c are each as defined in claim 1,
a 'is an integer of 0 to 4, b' is an integer of 0 to 2, b '' is an integer of 0 to 1, and c 'is an integer of 0 to 3. 1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound according to any one of claims 1 to 5. The method according to claim 6,
Wherein the compound is used as a host of the light emitting layer. The method according to claim 6,
Wherein the compound is used as a hole transporting layer material. The method according to claim 6,
Wherein the compound is used as a light emitting auxiliary layer material.