WO2016105123A2 - Organic compound and organic electroluminescent device comprising same - Google Patents

Abstract

The present invention relates to an organic electroluminescent device which comprises, in at least one organic layer, a novel compound having an excellent heat resistance, hole-transport capability, light-emitting capability and the like, and thereby has an improved luminous efficiency, driving voltage, lifespan and the like.

Description

Organic compound and organic electroluminescent device comprising the same

The present invention relates to a novel organic compound and an organic electroluminescent device comprising the same.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. The material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.

The light emitting material may be classified into blue, green, and red light emitting materials according to light emission colors. In addition, it can be divided into yellow and orange light emitting materials required to achieve a better natural color. In addition, a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer. The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. Since the development of phosphorescent materials can theoretically improve luminous efficiency up to four times compared to fluorescence, attention is being paid not only to phosphorescent dopants but also to phosphorescent host materials.

Hole injection layer, hole transport layer to date. NPB, BCP, Alq ₃ and the like are widely known as materials used for the hole blocking layer and the electron transporting layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as light emitting materials. Particularly, phosphorescent materials having great advantages in terms of efficiency improvement among light emitting materials include metal complex compounds including Ir such as Firpic, Ir (ppy) ₃ , and (acac) Ir (btp) ₂ , which are blue and green. It is used as a red dopant material. To date, CBP has shown excellent properties as a phosphorescent host material.

However, the conventional light emitting materials are good in terms of light emission characteristics, but the thermal stability is not very good due to the low glass transition temperature, and thus they are not satisfactory in terms of lifespan in the organic EL device. Therefore, there is a demand for the development of an organic EL device including a light emitting material having excellent performance.

On the other hand, in order to realize the practical use and characteristics of the organic electroluminescent device, not only the device is composed of the organic material layer having the multilayer structure as described above, but also the material of the device, in particular, the hole transport material should have thermal and electrical stable properties. Because, when a voltage is applied to the device, molecules with low thermal stability due to heat generated by the device have low crystal stability, resulting in rearrangement, and eventually crystallization occurs locally, resulting in an inhomogeneous part. This is because the concentration on the part causes degradation and destruction of the device.

Accordingly, in view of the above, conventionally used hole transport materials include m-MTDATA [4, 4 ', 4 "-tris (N-3-methylphenyl-N-phenylamino) -triphenylamine, 2-TNATA. [4, 4 ', 4-?-Tris (N- (naphthylene-2-yl) -N-phenylamino) -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, m-MTDATA and 2-TNATA have a low glass transition temperature (Tg) of 78 ° C. and 108 ° C., respectively, and have a problem in realizing full color because many problems occur during mass production. On the other hand, TPD and NPB also has a fatal disadvantage that the glass transition temperature (Tg) as low as 60 ℃ and 96 ℃, respectively, shorten the life of the device for the same reason. Accordingly, there is a demand for the development of an organic electroluminescent device capable of improving thermal stability, having excellent hole transporting ability, and improving the luminous efficiency and power efficiency of the organic electroluminescent device.

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

In addition, another object of the present invention is to provide an organic electroluminescent device having a low driving voltage, a high luminous efficiency, and an improved lifetime including the novel compound described above.

The present invention provides a compound represented by Formula 1:

(In 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 as or different from each other, and each independently deuterium, a halogen, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, and a nuclear atom having 3 to 40 heterocycloalkyl groups , C ₆ ~ C ₆₀ aryl group, nuclear atom 5 ~ 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group , C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine It may be selected from the group consisting of an oxide group and a C ₆ ~ C ₆₀ arylamine group, or may be combined with an adjacent substituent to form a condensed aromatic ring or a condensed heteroaromatic ring;

At least one of R ₁ to R ₄ is a substituent represented by Formula 2;

In Chemical Formula 2,

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

L ₁ is a single bond, or is C ₆ ~ C ₆₀ arylene group and a nucleus atoms is selected from the group consisting of a hetero arylene of 5 to 60;

Ar ₁ and and Ar ₂ are the same or different and are each independently a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, and the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~ C ₆₀ of It may be selected from the group consisting of an arylamine group, or Ar ₁ and Ar ₂ may be bonded to each other to form a ring,

Alkyl, aryl, heteroaryl and arylamine groups of Ar ₁ to Ar ₂ , alkyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkyloxy groups, aryloxy groups, and alkyl groups of R ₁ to R ₄ The silyl group, the arylsilyl group, the alkyl boron group, the aryl boron group, the aryl phosphine group, the aryl phosphine oxide group, the arylamine group, and the arylene group and heteroarylene group of L ₁ are deuterium, halogen, cyano, C _1- C ₄₀ alkyl group, C ₃ to C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C ₆ to C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ to C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, 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).

In addition, the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device comprising a.

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

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

EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated.

The compound according to the present invention is aryl at any one of the phenyl group moiety, one of both benzene moieties of carbazole, and the nitrogen moiety of carbazole, on the basic skeleton of the phenylcarbazole moiety having a phenyl group introduced at position 1 of the carbazole. A structure in which an amine group-containing substituent is introduced is represented by Chemical Formula 1. Here, the position number of carbazole can be represented as follows.

In the compound according to the present invention, a phenyl group is introduced at position 1 of the carbazole, such that the compound molecule is distorted, and thus, there is no problem of deterioration in luminescence properties due to pi-stacking. Therefore, the compound of the present invention can prevent the formation of excitation dimers (eximers), thereby improving the luminous efficiency of the OLED. In addition, since the compound of the present invention has a lower deposition temperature than a carbazole compound in which a phenyl group is introduced at position 1 of the carbazole, the thermal stability of the molecule may be enhanced.

In addition, the light emitting layer generally includes a host and a dopant to increase color purity and luminous efficiency. In this case, the host material should have a triplet energy gap of the host higher than the dopant. In particular, for the dopant to provide effective phosphorescence emission, the lowest excited state of the host must be higher in energy than the lowest emission state of the dopant. However, the phenylcarbazole moiety in the compound of the present invention has a wide 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, it can exhibit a higher energy level than the dopant, the light emitting performance of the OLED can be improved.

In addition, since the compound of the present invention has a high triplet energy gap as described above, it is possible to prevent the exciton generated in the light emitting layer from being diffused (moved) into the adjacent hole transport layer. Therefore, when the organic material layer (hereinafter referred to as "light emitting auxiliary layer") is formed between the hole transport layer and the light emitting layer using the compound of the present invention, the exciton is prevented from being diffused by the compound, thus including the light emitting auxiliary layer. Unlike conventional organic electroluminescent devices that do not, substantially the number of excitons that contribute to light emission in the light emitting layer can be improved to improve the luminous efficiency of the device.

In addition, both the arylamine group and the carbazole group are electron donating groups (EDGs) having large electron donating properties, and 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 the device performance can be improved when used as a hole transporting material of an OLED. Can be.

In addition, the compound represented by the general formula (1) of the present invention by introducing a variety of substituents in the basic skeleton, the molecular weight of the compound is significantly increased, and thus the glass transition temperature is improved according to the conventional CBP (4,4-dicarbazolybiphenyl) Higher thermal stability. In addition, the compound of the present invention is also effective in suppressing crystallization of the organic material layer.

As such, when the compound of the present invention is applied to an organic material layer material of the organic EL device, preferably, an emission layer material, a hole transport layer material, or an emission auxiliary layer material, the performance and lifespan characteristics of the organic EL device may be greatly improved. . As a result, the organic EL device may maximize the performance of the full color organic light emitting panel.

In Formula 1 according to the present invention, when a is 0, it means that hydrogen is not substituted with a substituent R ₁ , and when a is an integer of 1 to 5, R ₁ is as defined in Formula 1 above. In addition, when b is 0, it means that hydrogen is not substituted with a substituent R ₂ , and when b is an integer of 1 to 3, R ₂ is as defined in the formula (1). In addition, when c is 0, it means that hydrogen is not substituted with a substituent R ₃ , when c is an integer of 1 to 4, R ₃ is as defined in the 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.

R ₁ to R ₄ are the same as or different from each other, and each independently deuterium, a halogen, a cyano group, a C ₁ to C ₂₀ alkyl group, a C ₃ to C ₂₀ cycloalkyl group, and a nuclear atom having 3 to 20 heterocyclo Alkyl group, C ₆ ~ C ₄₀ aryl group, nuclear atom 5 to 40 heteroaryl group, C ₁ ~ C ₂₀ alkyloxy group, C ₆ ~ C ₄₀ aryloxy group, C ₁ ~ 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 preferably selected from the group consisting of a pin oxide group and an arylamine group of C ₆ to C ₄₀ . 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 contain a condensed aromatic ring or a heteroatom selected from N, P and S. Condensed heteroaromatic rings can be formed.

More preferably, R ₁ to R ₄ are the same as or different from each other, and are each independently composed of a C ₆ ~ C ₄₀ aryl group, a heteroaryl group of 5 to 40 nuclear atoms and an arylamine group of C ₆ ~ C ₄₀ Can be selected from the group.

However, at least one of R ₁ to R ₄ is a substituent represented by the formula (2).

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

In Formula 1, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently C ₁ ~ C ₂₀ Alkyl group, C ₆ ~ C ₄₀ An aryl group, and a nuclear atom of 5 to 40 heteroaryl group and It is preferably selected from the group consisting of C ₆ to C ₄₀ arylamine groups, or Ar ₁ and Ar ₂ are preferably bonded to each other to form a condensed ring.

Alkyl groups, aryl groups, heteroaryl groups, and arylamine groups of Ar ₁ to Ar ₂ ; An alkyl group, 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 arylphosphine group of R ₁ to R ₄ , Aryl phosphine oxide groups, arylamine groups; The allylene group and heteroarylene group of L ₁ are deuterium, halogen, cyano, an alkyl group of C ₁ to C ₄₀ (preferably an alkyl group of C ₁ to C ₂₀ ), a cycloalkyl group of C ₃ to C ₄₀ (preferably C A cycloalkyl group having ₃ to C ₂₀ ), a heterocycloalkyl group having 3 to 40 nuclear atoms (preferably a heterocycloalkyl group having 3 to 20 nuclear atoms), and an aryl group having a C ₆ to C ₆₀ (preferably C ₆ to) Aryl group of C ₄₀ ), heteroaryl group of 5 to 60 nuclear atoms (preferably heteroaryl group of 5 to 40 nuclear atoms), alkyloxy group of C ₁ to C ₄₀ (preferably C ₁ to C ₂₀ alkyloxy group), C ₆ to C ₆₀ aryloxy group (preferably, C ₆ to C ₄₀ aryloxy group), C ₁ to C ₄₀ alkylsilyl group (preferably, C ₁ to C ₂₀ Alkylsilyl group), C ₆ ~ C ₆₀ arylsilyl group (preferably C ₆ ~ C ₄₀ arylsilyl group), C ₁ ~ C ₄₀ alkyl boron group (preferably, C ₁ ~ C ₂₀ alkyl boron 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 An aryl phosphine oxide group) and a C ₆ to C ₆₀ arylamine group (preferably, a C ₆ to C ₄₀ arylamine group) and at least one substituent selected from the group consisting of (preferably 1 to 3 substituents) Substituted or unsubstituted. At this time, when the substituent is plural, they are the same or different from each other.

Examples of the substituent represented by Formula 2 include a substituent represented by the following Formula 3, but is not limited thereto.

In Chemical Formula 3,

L ₁ , Ar ₁ and Ar ₂ are the same as defined in Chemical 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 hydrogen, deuterium (D), C ₁ -C ₄₀ alkyl group (preferably C ₁ -C ₂₀ alkyl group), C ₆ -C ₆₀ aryl group (preferably C ₆ -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 a C ₆ to C ₆₀ (preferably an arylamine group having C ₆ to C ₃₀ ) Or a condensed aromatic ring or a condensed heteroaromatic ring can be combined with an adjacent substituent;

At this time, the aryl group, heteroaryl group and arylamine group of R ₅ are each independently deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group (preferably C ₁ ~ C ₂₀ alkyl group), C ₃ ~ C ₄₀ cycloalkyl groups (preferably, C ₃ ~ C ₂₀ cycloalkyl group), nuclear atoms, 3 to 40 heterocycloalkyl group (preferably, the number of nuclear atoms of 3 to 20 heterocycloalkyl group of a) the, C ₆ ~ C ₆₀ aryl group (Preferably, an aryl group having ₆ to ₃₀ carbon atoms), a heteroaryl group having 5 to 60 nuclear atoms (preferably a heteroaryl group having 5 to 30 nuclear atoms), an alkyloxy group having ₁ to ₄₀ carbon atoms ( Preferably, C ₁ ~ C ₂₀ Alkyloxy group), C ₆ ~ C ₆₀ An aryloxy group (preferably, C ₆ ~ C ₃₀ An aryloxy group), C ₁ ~ C ₄₀ Alkylsilyl group (preferably , C ₁ to C ₂₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group (preferably, C ₆ to C ₃₀ arylsilyl group), C ₁ to C ₄₀ alkyl boron 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 1 selected from the group consisting of a pin oxide group (preferably an C ₆ -C ₃₀ arylphosphine oxide group) and a C ₆ -C ₆₀ arylamine group (preferably a C ₆ -C ₃₀ arylamine group) When substituted or unsubstituted with at least one substituent, provided that the substituents are 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 Chemical Formulas 4 to 7,

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

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

Examples of the compound represented by Chemical Formula 1 include a compound represented by the following Chemical Formulas 8 to 11, but are not limited thereto.

In Chemical Formulas 8 to 11,

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

a 'is an integer of 0-4, b' is an integer of 0-2, b "is an integer of 0-1, c 'is an integer of 0-3.

The compound represented by Formula 1 according to the present invention may be embodied by the following compounds, but is not limited thereto.

As used herein, "unsubstituted alkyl" refers to a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms, non-limiting examples of which are 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 (saturated cyclic hydrocarbon) having 3 to 40 carbon atoms. 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 in the ring , Preferably 1 to 3 carbons are substituted with a hetero atom 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, alone or in combination of two or more rings. In this case, the two or more rings may be attached in a simple or condensed form with each other. Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl and the like.

As used herein, "unsubstituted heteroaryl" is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, and at least one carbon in the ring, preferably Preferably 1 to 3 carbons are substituted with heteroatoms such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se). In this case, the heteroaryl may be attached in a form in which two or more rings are simply attached or condensed with each other, and may also include a condensed form with an aryl group. Non-limiting examples of such heteroaryls include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl and the like.

As used herein, "unsubstituted alkyloxy" refers to a monovalent functional group represented by RO-, wherein R is alkyl having 1 to 40 carbon atoms, and is linear, branched or cyclic. ) May include a 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" refers to a monovalent functional group represented by R'O-, wherein 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, "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, and " Unsubstituted arylamine "means an amine substituted with aryl having 6 to 60 carbon atoms.

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

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

Compounds of formula 1 of the present invention can be synthesized according to general synthetic methods ( Chem . Rev. , 60 : 313 (1960); J. Chem . SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995) ) And so on). Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.

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

Specifically, the present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, and at least one of the organic material layers includes a compound represented by Chemical Formula 1. In this case, the compound may be used alone or in combination of two or more.

According to an example of the present invention, the one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer includes the compound, preferably the light emitting layer or The hole transport layer may comprise the 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 life of the organic electroluminescent device can be improved.

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

According to another example of the present invention, the at least one organic material layer includes a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer, preferably a light emitting auxiliary layer It may include a compound represented by the formula (1). In particular, when the compound is used as a light emitting auxiliary layer material of the organic light emitting device, the efficiency (light emitting efficiency and power efficiency), life, brightness and driving voltage of the organic light emitting device can be improved.

The structure of the organic EL device of the present invention is not particularly limited, and for example, the anode, one or more organic material layers and the cathode are sequentially stacked on the substrate, and an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer. Can be.

According to an example, the organic EL device may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked on a substrate. Optionally, a light emission auxiliary layer may be inserted between the hole transport layer and the light emitting layer. In addition, an electron injection layer may be positioned on the electron transport layer.

The organic electroluminescent device of the present invention is a material known in the art, except that at least one of the one or more organic material layers (eg, the light emitting layer or the light emitting auxiliary layer) is formed to include the compound represented by Chemical Formula 1 above. And by forming the organic layer and the electrode using the 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 the substrate usable in the present invention include a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet, but are not limited thereto.

In addition, examples of the anode 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), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is not limited thereto.

Further, 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; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

In addition, the material used as the hole injection layer, the hole transport layer, the electron injection layer and the electron transport 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 merely to illustrate the present invention and the present invention is not limited by the following examples.

[ Preparation  One] Core1  synthesis

<Step 1> 5- chloro -2-nitro-5'-phenyl-1,1 ': 3', 1 ''- terphenyl  synthesis

4-chloro-2-iodo-1-nitrobenzene 30 g (105.84 mmol), [1,1 ': 3', 1 ''-terphenyl] -5'-ylboronic acid 34.8 g (127 mmol), K ₂ under nitrogen stream 43.88 g (317.52 mmol) of CO ₃ and 400 ml / 100 ml of 1,4-Dioxane / H ₂ O were added thereto and stirred. 3.7 g (3.175 mmol) of Pd (PPh ₃ ) ₄ was added at 40 ° C., and the mixture was stirred under reflux for 12 hours at 110 ° C. After completion of the reaction, the organic layer was extracted with dichloromethane, the organic layer was dried over MgSO ₄ and filtered under reduced pressure. After distilling under reduced pressure on the filtered organic layer, 5-chloro-2-nitro-5'-phenyl-1,1 ': 3', 1 ''-terphenyl (32 g, yield: 78%) was purified by column chromatography. Got it.

¹ H-NMR: δ 7.32 (m, 2H), 7.53 (m, 4H), 7.78 (m, 5H), 8.08 (m, 3H), 8.25 (s, 1H), 8.44 (d, 1H)

<Step 2> 6- chloro -1,3- diphenyl -9H- of carbazole  synthesis

30 g (82.93 mmol) of 5-chloro-2-nitro-5'-phenyl-1,1 ': 3', 1 ''-terphenyl synthesized in <Step 1> under nitrogen stream, 43.5 g (165.86 mmol) triphenylphosphine , And 300 ml of 1,2-dichlorobenzene were added and stirred under reflux at 180 ° C. for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed by distillation, and the organic layer was extracted with dichloromethane. The extracted organic layer was dried over 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 using column chromatography.

¹ H-NMR: δ 7.15 (m, 5H), 7.58 (m, 6H), 7.75 (m, 3H), 8.03 (s, 1H), 12.25 (s, 1H)

<Step 3> Core1  Synthesis of

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

After the reaction was terminated, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer was purified by column chromatography to give the 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  2] Core2  synthesis

<Step 1> 5- chloro -2-nitro-5'-phenyl-1,1 ': 2', 1 ''- terphenyl  synthesis

[1,1 ': 4', 1 ''-terphenyl] -2 instead of [1,1 ': 3', 1 ''-terphenyl] -5'-ylboronic acid used in <Step 1> of Preparation Example 1 Except for using 34.8 g (127 mmol) of '-ylboronic acid, 5-chloro-2-nitro-5'-phenyl-1,1': 2 was carried out in the same manner as in <Step 1> of Preparation Example 1. ', 1' '-terphenyl (31 g, yield: 75%) was obtained.

¹ H-NMR: δ 7.36 (m, 7H), 7.88 (m, 5H), 8.25 (m, 2H), 8.52 (m, 2H)

<Step 2> 6- chloro -1,4- diphenyl -9H- of carbazole  synthesis

5-chloro-2-synthesized in <Step 1> instead of 5-chloro-2-nitro-5'-phenyl-1,1 ': 3', 1 ''-terphenyl used in <Step 2> of Preparation Example 1 Except for using 30 g (82.93 mmol) of 2-nitro-5'-phenyl-1,1 ': 2', 1 ''-terphenyl, the same procedure as in <Step 2> of Preparation Example 1 was performed. -Chloro-1,4-diphenyl-9H-carbazole (19 g, yield: 64%) was obtained.

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 of

Except for using 20 g (56.52 mmol) of 6-chloro-1,4-diphenyl-9H-carbazole instead of 6-chloro-1,3-diphenyl-9H-carbazole used in <Step 3> of Preparation Example 1. , The same procedure as in <Step 3> of Preparation Example 1 was 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  3] Core3  Synthesis of

20 g (56.52 mmol) of 6-chloro-1,3-diphenyl-9H-carbazole obtained in <Step 2> of Preparation Example 1 under nitrogen stream, 8.27 g (67.82 mmol) of phenylboronic acid, 55.2 g (169.56 Cs ₂ CO ₃ ) mmol), 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 at 40 ° C., and the mixture was stirred under reflux at 110 ° C. for 12 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, the organic layer was dried over MgSO ₄ and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and then Compound Core 3 (16 g, yield: 71%) was obtained by column chromatography.

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  4] Core4  Synthesis of

Instead of 6-chloro-1,3-diphenyl-9H-carbazole used in Preparation Example 3, 20 g (56.52 mmol) of 6-chloro-1,4-diphenyl-9H-carbazole obtained in <Step 2> of Preparation Example 2 was used. Except that, Core4 (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  5] Core5  Synthesis of

<Step 1> 4- chloro -2-nitro-5'-phenyl-1,1 ': 3', 1 ''- terphenyl  synthesis

30 g (105.83 mmol) of 4-chloro-2-iodo-1-nitrobenzene, [1,1 ': 3', 1 ''-terphenyl] -5'-ylboronic acid, 34.8 g (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 thereto and stirred. 3.7 g (3.175 mmol) of Pd (PPh ₃ ) ₄ was added at 40 ° C., and the mixture was stirred under reflux at 110 ° C. for 12 hours. After completion of the reaction, the organic layer was extracted with dichloromethane, the organic layer was dried over MgSO ₄ and filtered under reduced pressure. After distillation under reduced pressure the filtered organic layer was purified by column chromatography to give 4-chloro-2-nitro-5'-phenyl-1,1 ': 3', 1 ''-terphenyl (32g, yield: 78%). .

¹ H-NMR: δ 7.51 (m, 6H), 7.82 (m, 4H), 8.05 (m, 5H), 8.52 (s, 1H)

<Step 2> 7- chloro -1,3- diphenyl -9H- of carbazole  synthesis

4-chloro- synthesized in <Step 1> instead of 5-chloro-2-nitro-5'-phenyl-1,1 ': 3', 1 ''-terphenyl used in <Step 2> of Preparation Example 1 Except for using 30 g (82.93 mmol) of 2-nitro-5'-phenyl-1,1 ': 3', 1 ''-terphenyl, the same procedure as in <Step 2> of Preparation Example 1 was performed. -chloro-1,3-diphenyl-9H-carbazole (20 g, yield: 67%) was obtained.

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 of

Except for using 6-chloro-1,3-diphenyl-9H-carbazole 20g (56.52 mmol) instead of 6-chloro-1,3-diphenyl-9H-carbazole used in Preparation Example 3, the same as in Preparation Example 3 The procedure was carried out to obtain compound Core5 (16 g, yield: 71%).

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  6] Core6  Synthesis of

<Step 1> 1- chloro -3- methoxy -9-phenyl-9H- carbazole  Synthesis of

Preparation was carried out, except that 20 g (86.33 mmol) of 1-chloro-3-methoxy-9H-carbazole was used instead of 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)

<Step 2> 3- methoxy -1,9- diphenyl -9H- of carbazole  synthesis

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> of Preparation Example 1, [1 Except for using 9.5 g (77.97 mmol) of Phenyl boronic acid instead of, 1 ': 3', 1 ''-terphenyl] -5'-ylboronic acid, the same procedure as in <Step 1> of Preparation Example 1 was performed. 3-methoxy-1,9-diphenyl-9H-carbazole (16 g, yield: 70%) was obtained.

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)

<Step 3> 1,9- diphenyl -9H- carbazol -3- ol  Synthesis of

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

¹ H-NMR: δ 7.18 (m, 5H), 7.51 (m, 9H), 8.02 (d, 1H), 8.68 (d, 1H) 9.45 (s, 1H)

<Step 4> Synthesis of Core 6

Under nitrogen stream, 6 g of 1,9-diphenyl-9H-carbazol-3-ol obtained in <Step 3>, (17.88 mmol), 2.5 g (8.94 mmol) of Trifluoromethanesulfonic anhydride, and 10 g (17.88 mmol) of Pyridine were diluted to 100 mL. The mixture was added to dichloro methan and stirred at 0 ° C. for 1 hour. After completion of the reaction, the organic layer was extracted with dichloromethane, the organic layer was dried over MgSO ₄ and filtered under reduced pressure. After distilling the filtered organic layer under reduced pressure, Core 6 (5.8 g, yield: 69%) was obtained by using 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)

[ Synthesis Example  1] Compound Inv  1, Synthesis

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

After the reaction was completed, the organic layer was extracted with ethyl acetate, water was removed with MgSO ₄ from the organic layer, and purified by column chromatography to obtain Inv 1 (2.8 g, yield: 53%) as a target compound.

GC-Mass (Theoretical value: 754.98 g / mol, Measured value: 754 g / mol)

[ Synthesis Example  2] compound Inv  13 Synthesis

Di ([1,1'-biphenyl] -4- in place of N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine used in Example 1 Except for using yl) amine (2.4 g, 7.66 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain Inv 13 (2.6 g, yield: 52%) as a target compound.

GC-Mass (Theoretical value: 714.91 g / mol, Measured value: 714 g / mol)

[ Synthesis Example  3] compound Inv  Synthesis of 37

3 g (6.97 mmol) of the compound of Preparation Example 1, (4-([1,1'-biphenyl] -4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl under nitrogen stream ) Boronic acid 3.38 g (7.66 mmol), K ₂ CO ₃ 2.89 g (20.91 mmol) and 1,4-Dioxane / H ₂ O 100ml / 250 ml were added and stirred. Pd (PPh ₃ ) ₄ at 40 ° C 0.24 g (0.209 mmol) was added thereto, and the mixture was stirred under reflux at 110 ° C. for 12 hours. After completion of the reaction, the mixture 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 column chromatography was used to obtain Inv37 (3.5 g, yield: 60%) as a target compound.

GC-Mass (Theoretical value: 831.08 g / mol, Measured value: 831 g / mol)

[ Synthesis Example  4] compound Inv  Synthesis of 49

Instead of (4-([1,1'-biphenyl] -4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid used in Synthesis Example 3 (4- (di ( Inv 49 (3.6 g) was prepared by the same procedure as in Synthesis Example 3, except that 3.38 g (7.66 mmol) of [1,1'-biphenyl] -4-yl) amino) phenyl) boronic acid was used. , Yield: 65%).

GC-Mass (Theoretical value: 791.01 g / mol, Measured value: 791 g / mol)

[ Synthesis Example  5] compound Inv  70 composites

Instead of (4-([1,1'-biphenyl] -4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid used in Synthesis Example 3 (4- (bis ( Aside from using 4.0 g (7.66 mmol) of 9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid, Inv 70 (3.8) g, yield: 63%).

GC-Mass (Theoretical value: 871.14 g / mol, Measured value: 871 g / mol)

[ Synthesis Example  6] compound Inv  87 composites

(4- (diphenylamino) instead of (4-([1,1'-biphenyl] -4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid used in Synthesis Example 3 Except for using 2.21 g (7.66 mmol) of phenyl) boronic acid, Inv 87 (2.8 g, yield: 62%) was obtained by the same procedure as in Synthesis Example 3.

GC-Mass (Theoretical value: 638.8 g / mol, Measured value: 638 g / mol)

[ Synthesis Example  7] compound Inv  89 Synthesis

(4 '-([instead of (4-([1,1'-biphenyl] -4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid used in Synthesis Example 3 1,1'-biphenyl] -4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino)-[1,1'-biphenyl] -4-yl) boronic acid 4.27 g (7.66 mmol) Except for using, the same procedure as in Synthesis Example 3 was performed to obtain Inv 89 (4.0 g, yield: 63%) as the target compound.

GC-Mass (Theoretical value: 907.17 g / mol, Measured value: 907 g / mol)

[ Synthesis Example  8] compound Inv Of 91  synthesis

(3 '-([instead of (4-([1,1'-biphenyl] -4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid used in Synthesis Example 3 1,1'-biphenyl] -4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino)-[1,1'-biphenyl] -4-yl) boronic acid 4.27 g (7.66 mmol) Except for using the same procedure as in Synthesis Example 3 to obtain the title compound Inv 91 (4.2 g, yield: 66%).

GC-Mass (Theoretical value: 907.17 g / mo, Measured value: 907 g / mol)

[ Synthesis Example  9] Compound Inv  Synthesis of 93

Inv 93 (2.9g, Yield) of the target compound was carried out in the same manner as in Synthesis Example 1, except that 3.0 g (6.97 mmol) of Compound Core2 synthesized in Preparation Example 2 was used instead of Compound Core1 used in Synthesis Example 1. : 55%).

GC-Mass (Theoretical value: 822.87 g / mol, Measured value: 822 g / mol)

[ Synthesis Example  10] compound Inv  105 composites

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 instead of the compound Core1, and Inv 105 (2.7 g, yield: 54%).

GC-Mass (Theoretical value: 714.91 g / mol, Measured value: 714 g / mol)

[ Synthesis Example  11] Compound Inv  Synthesis of 129

Inv 129 (3.3 g, Yield: 60) was the same compound as in Synthesis Example 3, except that 3.0 g (6.97 mmol) of Compound Core2 of Preparation Example 2 was used instead of Compound Core1 used in Synthesis Example 3. %) Was obtained.

GC-Mass (Theoretical value: 831.09 g / mol, Measured value: 831 g / mol)

[ Synthesis Example  12] compounds Inv  Synthesis of 141

Inv 141 (2.9 g, Yield: 55) was obtained by the same procedure as in Synthesis Example 4, except that 3.0 g (6.97 mmol) of Compound Core2 of Preparation Example 2 was used instead of Compound Core1 used in Synthesis Example 4. %) Was obtained.

GC-Mass (Theoretical value: 791.01 g / mol, Measured value: 791 g / mol)

[ Synthesis Example  13] compound Inv  183 Synthesis

Inv 183 (3.9 g, Yield: 61) was the same compound as in Synthesis Example 8, except that 3.0 g (6.97 mmol) of Compound Core2 of Preparation Example 2 was used instead of Compound Core1 used in Synthesis Example 8. %) Was obtained.

GC-Mass (Theoretical value: 907.17 g / mol, Measured value: 907 g / mol)

[ Synthesis Example  14] compound Inv  Synthesis of 221

3.0 g (7.58 mmol) of Core3 obtained in Preparation Example 3, N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H-fluoren under nitrogen stream 4.7g (9.10 mmol) of 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 stirred under reflux at 190 ° C. for 12 hours.

After the reaction was terminated, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent of the organic layer was purified by column chromatography to give the title compound Inv 221 (3.8 g, yield 60%).

GC-Mass (Theoretical value: 831.08 g / mol, Measured value: 831 g / mol)

[ Synthesis Example  15] compound Inv  Synthesis of 227

N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H-fluoren-2-amine instead of N-([1,1'-biphenyl] The same procedure as in Synthesis Example 14 was carried out except that 4-yl) -N- (4-bromophenyl) -9,9-diphenyl-9H-fluoren-2-amine (5.83 g, 9.1 mmol) was used. Inv 227 (4.4 g, yield 61%) was obtained as the target compound.

GC-Mass (Theoretical value: 955.22 g / mol, Measured value: 955 g / mol)

[ Synthesis Example  16] compound Inv  Synthesis of 233

N-([1 instead of N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H-fluoren-2-amine used in Synthesis Example 14. Synthesis Example 14, except that 4.33 g (9.1 mmol) of 1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1,1'-biphenyl] -4-amine was used. In the same procedure, the title compound Inv 233 (4.0 g, yield 66%) was obtained.

GC-Mass (Theoretical value: 791.01 g / mol, Measured value: 791 g / mol)

[ Synthesis Example  17] compound Inv  Synthesis of 254

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

GC-Mass (Theoretical value: 871.14 g / mol, Measured value: 871 g / mol)

[ Synthesis Example  18] compound Inv  Synthesis of 273

N-([1 instead of N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H-fluoren-2-amine used in Synthesis Example 14. , 1'-biphenyl] -4-yl) -N- (4'-bromo- [1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine 5.39 g ( 9.1 mmol) was obtained, and the same procedure as in Synthesis Example 14 was performed, thereby obtaining Inv 273 (4.5 g, 65% yield) of the title compound.

GC-Mass (Theoretical value: 907.17 g / mol, Measured value: 907 g / mol)

[ Synthesis Example  19] compound Inv  Synthesis of 313

Inv 313 (4.3 g, Yield 68%) was obtained by the same procedure as Synthesis Example 14, except that 3.0 g (7.58 mmol) of Core4 obtained in Preparation Example 4 was used instead of Core3 used in Synthesis Example 14. Got.

GC-Mass (Theoretical value: 831.08 g / mol, Measured value: 831 g / mol)

[ Synthesis Example  20] compound Inv  Synthesis of 319

A target compound Inv319 (4.8 g, 66%) was obtained in the same manner as in Synthesis Example 15, except that 3.0 g (7.58 mmol) of Core4 obtained in Preparation Example 4 was used instead of Core3 used in Synthesis Example 15. Got it.

GC-Mass (Theoretical value: 955.22 g / mol, Measured value: 955 g / mol)

[ Synthesis Example  21] Inv  Synthesis of 325

Inv 325 (3.9 g, Yield 65%) was obtained by the same procedure as Synthesis Example 16, except that 3.0 g (7.58 mmol) of Core4 obtained in Preparation Example 4 was used instead of Core 3 used in Synthesis Example 16. )

GC-Mass (Theoretical value: 791.01 g / mol, Measured value: 791 g / mol)

[ Synthesis Example  22] compound Inv  Synthesis of 346

Inv 346 (4.2 g, 63% yield) of the target compound was obtained in the same manner as in Synthesis Example 17, except that 3.0 g (7.58 mmol) of Core4 obtained in Preparation Example 4 was used instead of Core3 used in Synthesis Example 17. Got.

GC-Mass (Theoretical value: 871.14 g / mol, Measured value: 871 g / mol)

[ Synthesis Example  23] compound Inv  Synthesis of 365

Inv 365 (4.4 g, 64%) was obtained by the same procedure as Synthesis Example 18, except that 3.0 g (7.58 mmol) of Core4 obtained in Preparation Example 4 was used instead of Core3 used in Synthesis Example 18. Got.

GC-Mass (Theoretical value: 907.17 g / mol, Measured value: 907 g / mol)

[ Synthesis Example  24] compound Inv  405 Synthesis

Inv 405 (4.1 g, 65%) of the target compound was obtained in the same manner as in Synthesis Example 14, except that 3.0 g (7.58 mmol) of Core5 obtained in Preparation Example 5 was used instead of Core3 used in Synthesis Example 14. Got.

GC-Mass (Theoretical value: 831.08 g / mol, Measured value: 831 g / mol)

[ Synthesis Example  25] compound Inv  Synthesis of 411

Inv 411 (4.5 g, 62%) was obtained by the same procedure as in Synthesis Example 15, except that 3.0 g (7.58 mmol) of Core5 obtained in Preparation Example 5 was used instead of Core3 used in Synthesis Example 15. Got.

GC-Mass (Theoretical value: 955.22 g / mol, Measured value: 955 g / mol)

[ Synthesis Example  26] compound Inv  Synthesis of 417

Inv 417 (3.9 g, Yield 65%) was obtained by the same procedure as Synthesis Example 16, except that 3.0 g (7.58 mmol) of Core5 obtained in Preparation Example 5 was used instead of Core3 used in Synthesis Example 16. Got.

GC-Mass (Theoretical value: 791.01 g / mol, Measured value: 791 g / mol)

[ Synthesis Example  27] compound Inv  Synthesis of 457

Inv 457 (4.3 g, 63% yield) of the target compound was obtained in the same manner as in Synthesis Example 18, except that 3.0 g (7.58 mmol) of Core5 obtained in Preparation Example 5 was used instead of Core3 used in Synthesis Example 18. Got.

GC-Mass (Theoretical value: 907.17 g / mol, Measured value: 907 g / mol)

[ Synthesis Example  28] compound Inv  459 Synthesis

Instead of Core3 used in Synthesis Example 14, 3.0 g (7.58 mmol) of Core5 obtained in Preparation Example 5 were used, and N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9 N-([1,1'-biphenyl] -4-yl) -N- (4'-bromo- [1,1'-biphenyl] -3-yl instead of, 9-dimethyl-9H-fluoren-2-amine Inv 459 (4.2 g, 61% yield) was performed by the same procedure as in Synthesis Example 14, except that 5.38 g (9.1 mmol) of 9,9-dimethyl-9H-fluoren-2-amine was used. )

GC-Mass (Theoretical value: 907.17 g / mol, Measured value: 907 g / mol)

[ Synthesis Example  29] compound Inv Of 588  synthesis

Inv 588 (3.3) was carried out in the same manner as in Synthesis Example 3, except that Core 6 3g, (6.41 mmol), synthesized in <Step 4> of Preparation Example 6 was used instead of Core1 used in Synthesis Example 3. g, yield 68%) was obtained.

GC-Mass (Theoretical value: 754.98 g / mol, Measured value: 754 g / mol)

[ Synthesis Example  30] compound Inv 600 of  synthesis

Inv 600 (3.1) was prepared by the same procedure as in Synthesis Example 4, except that 3g of Core 6 synthesized in <Step 4> of Preparation Example 6 and (6.41 mmol) were used instead of Core1 used in Synthesis Example 4. g, yield 68%) was obtained.

GC-Mass (Theoretical value: 714.91 g / mol, Measured value: 714 g / mol)

[ Synthesis Example  31] Compound Inv  Synthesis of 638

Except for using Core 1 3g, (6.41 mmol) synthesized in <Step 4> of Preparation Example 6 instead of Core1 used in Synthesis Example 6, the same procedure as in Synthesis Example 6 was performed to obtain Inv 638 ( 2.5 g, yield 70%) was obtained.

GC-Mass (Theoretical value: 562.72 g / mol, Measured value: 562 g / mol)

[ Synthesis Example  32] compound Inv 680 of  synthesis

Inv 680 (the target compound) was prepared in the same manner as in Synthesis Example 3, except that 3.0 g (8.47 mmol) of 1-chloro-3,9-diphenyl-9H-carbazole was used instead of Core1 used in Synthesis Example 3. 4.0 g, yield 62%) was obtained.

GC-Mass (Theoretical value: 754.98 g / mol, Measured value: 754 g / mol)

[ Synthesis Example  33] Compound Inv  Synthesis of 692

Instead of (4-([1,1'-biphenyl] -4-yl (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid used in Synthesis Example 32 (4- (di ( Inv 692 (3.8 g) was prepared by the same procedure as in Synthesis Example 32, except that 4.54 g (10.16 mmol) of [1,1'-biphenyl] -4-yl) amino) phenyl) boronic acid was used. , Yield 63%) was obtained.

GC-Mass (Theoretical value: 714.91 g / mol, Measured value: 714 g / mol)

[ Synthesis Example  34] Compound C- 1 of  synthesis

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

Instead of Core1 used in Synthesis Example 3, 10 g (49.59 mmol) of 1-chloro-9H-carbazole was used, and (4-([1,1'-biphenyl] -4-yl (9,9-dimethyl-9H-fluoren) 1-phenyl-9H-carbazole (8.5 g, yield) was carried out in the same manner as in Synthesis Example 3, except that 7.25 g (59.5 mmol) of Phenyl boronic acid was used instead of -2-yl) amino) phenyl) boronic acid. : 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

A target compound C was prepared by the same procedure as in Synthesis Example 14, except that 8.5g (34.93 mmol) of 1-phenyl-9H-carbazole synthesized in <Step 1> was used instead of Core3 used in Synthesis Example 14. -1 (16 g, yield: 67%) was obtained.

GC-Mass (Theoretical value: 678.88 g / mol, Measured value: 678 g / mol)

[ Synthesis Example  35] Compound C- 2 of  synthesis

<Step 1> 1,4- diphenyl -2,3,4,9- tetrahydro -1H- of carbazole  synthesis

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 added under a nitrogen stream, and the mixture was stirred under reflux at 120 ° C. for 12 hours. After completion of the reaction, the acetic acid was removed, the organic layer was extracted with sodium bicarbonate and 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 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)

<Step 2> 1,4- diphenyl -9H- of carbazole  synthesis

Under nitrogen stream, 43 g (133.12 mmol) of 1,4-diphenyl-2,3,4,9-tetrahydro-1H-carbazole and 300 ml of Benzene obtained in <Step 1> were added, followed by DDQ 60 for 5 minutes. Divided g (264.24 mmol) and stirred for 1 hour. After completion of the reaction, the mixture was filtered through Silicagel and Celite, Benzene was removed, and the organic layer was extracted with dichloromethane. The extracted organic layer was dried over 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 using column chromatography.

¹ H-NMR: δ 7.22 (m, 5H), 7.42 (m, 4H), 7.68 (d, 1H), 7.82 (m, 2H), 8.19 (m, 3H), 12.18 (s, 1H)

Step 3 Synthesis of Compound C-2

Except for using the 1,4-diphenyl-9H-carbazole 10g (31.3 mmol) in the above <Step 2> instead of the Core3 used in Synthesis Example 14, the target compound C- 2 (15.8 g, yield: 67%) was obtained.

GC-Mass (Theoretical value: 754.98 g / mol, Measured value: 754 g / mol)

[ Example  1]-Fabrication of Organic EL Device

A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then washed the substrate using UV for 5 minutes The substrate was then transferred to a vacuum depositor.

M-MTDATA (60 nm) on the ITO transparent electrode prepared as described above / Compound Inv 1 (80 nm) synthesized in Synthesis Example 1 / [DS-H522 + 5% DS-501] (30 nm) / BCP (10 nm) An organic EL device was manufactured in the order of / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm).

DS-H522 and DS-501 used above are products of Doosan Corporation BG, and the structures of m-MTDATA and BCP are as follows.

[ Example  2 to 35]-Fabrication of Organic EL Device

An organic EL device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 were used instead of the compound Inv 1 used as the hole transport layer material in forming the hole transport layer in Example 1.

[ Comparative example  1]-Fabrication of organic EL device

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

[ Evaluation example  One]

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

Sample	Hole transport layer	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, the organic EL device (the organic EL device of Examples 1 to 35) using the compounds (Inv 1 to Inv 417, C-1 to C-2) according to the present invention as a hole transport layer is conventionally Compared with the organic EL element (the organic EL element of Comparative Example 1) using NPB, it was found to exhibit better performance in terms of current efficiency and driving voltage.

In addition, the organic EL device of Example 14 using the compound Inv 221 having a phenyl group introduced at positions 1, 3, and 6 of the carbazole, as a hole transport layer, has a compound C-1 having a phenyl group introduced at position 1 of the carbazole, Compared with the organic EL devices of Examples 34 to 35 using the compound C-2 having the phenyl group introduced at the carbazole positions 1 and 4 as the hole transporting layer, it was found to have better performance in terms of current efficiency and driving voltage.

[ Example  36]-green organic Electric field  Manufacture of light emitting device

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

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

On the ITO transparent electrode prepared as above, m-MTDATA (60 nm) / TCTA (80 nm) / Inv 1 (40 nm) / CBP + 10% Ir (ppy) ₃ (30 nm) / BCP (10 nm) / An organic electroluminescent device was manufactured by stacking in order of Alq3 (30 nm) / LiF (1 nm) / Al (200 nm).

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

[ Example  37-63]-green organic Electric field  Manufacture of light emitting device

A green organic EL device was manufactured in the same manner as in Example 36, except that each of the compounds shown in Table 2 was used instead of the compound Inv 1 used as the emission auxiliary layer material in the formation of the emission auxiliary layer in Example 36. It was.

[ Comparative example  2]-green organic Electric field  Manufacture of light emitting device

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

[ Evaluation example  2]

For organic electroluminescent devices prepared in Examples 36 to 63, and Comparative Example 2, driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below. .

Sample	Luminous auxiliary layer	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, the green organic electroluminescent device (the green organic electroluminescent device of Examples 36 to 63) using the compound represented by Chemical Formula 1 according to the present invention as the light emitting auxiliary layer material, has no light emitting auxiliary layer material. Compared with the conventional green organic EL device (the organic EL device of Comparative Example 2) using only CBP as the light emitting layer material, it was found that the driving voltage was similar but the light emission efficiency was improved.

[ Example  64]-red organic Electric field  Manufacture of light emitting device

After the high purity sublimation purification of the compound Inv 1 synthesized in Synthesis Example 1 by a known method, a red organic electroluminescent device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 mm 3 was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes And the substrate was transferred to a vacuum evaporator.

On the prepared ITO transparent electrode, m-MTDATA (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) was laminated in order to prepare a red organic electroluminescent device.

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

[ Example  65-91]-red organic Electric field  Manufacture of light emitting device

A red organic EL device was manufactured in the same manner as in Example 64, except that each of the compounds shown in Table 3 was used instead of the compound Inv 1 used as the emission auxiliary layer material in the formation of the emission auxiliary layer in Example 64. It was.

[ Comparative example  3]-red organic Electric 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]

For the organic electroluminescent devices prepared in Examples 64 to 91, and Comparative Example 3, the driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 3 below. .

Sample	Luminous auxiliary layer	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	3.32	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 Table 3, the red organic electroluminescent device (the red organic electroluminescent device of Examples 64 to 91) using the compound represented by Formula 1 according to the present invention as a light emitting auxiliary layer material is conventionally used without a light emitting auxiliary layer. Compared with the red organic electroluminescent element (the organic electroluminescent element of Comparative Example 3) using only CBP as the material of the light emitting layer, the driving voltage was similar but the light emission efficiency was improved.

[ Example  92]-blue organic Electric field  Manufacture 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 EL device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 mm 3 was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes And the substrate was transferred to a vacuum evaporator.

On the prepared ITO transparent electrode, DS-205 (Doosan) (80 nm) / NPB (15 nm) / Compound Inv 1 (15nm) / ADN + 5% DS-405 (Doosan) (30nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) in order to prepare a blue organic electroluminescent device.

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

[ Example  93 to 119]-blue organic Electric field  Manufacture of light emitting device

A blue organic EL device was manufactured in the same manner as in Example 92, except that each of the compounds shown in Table 4 was used instead of the compound Inv 1 used as the emission auxiliary layer material in the formation of the emission auxiliary layer in Example 92. It was.

[ Comparative example  4]-blue organic Electric field  Fabrication of light emitting device

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

[ Evaluation example  4]

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

Sample	Luminous auxiliary layer	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	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 device (the blue organic electroluminescent device of Examples 92 to 119) using the compound represented by Formula 1 according to the present invention as a light emitting auxiliary layer material is conventionally provided without a light emitting auxiliary layer. Compared with the blue organic electroluminescent element (the organic electroluminescent element of Comparative Example 4) including only the light emitting layer of ADN, it was found that the driving voltage was similar but the light emission efficiency was improved.

Claims (9)

1. Compound represented by the following formula (1):

   [Formula 1]

   

   (In 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 as or different from each other, and each independently deuterium, a halogen, a cyano group, a C ₁ to C ₄₀ alkyl group, a C ₃ to C ₄₀ cycloalkyl group, and a nuclear atom having 3 to 40 heterocycloalkyl groups , C ₆ ~ C ₆₀ aryl group, nuclear atom 5 ~ 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group , C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine It may be selected from the group consisting of an oxide group and a C ₆ ~ C ₆₀ arylamine group, or may be combined with an adjacent substituent to form a condensed aromatic ring or a condensed heteroaromatic ring;

   At least one of R ₁ to R ₄ is a substituent represented by Formula 2;

   [Formula 2]

   

   * Is a site where a bond is made to at least one of R ₁ to R ₄ ;

   L ₁ is a single bond or, C ₆ ~ C ₆₀ aryl group and can be selected from the group consisting of 5 to 60 nucleus atoms heteroarylene group;

   Ar ₁ and and Ar ₂ are the same or different and are each independently a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, and the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~ C ₆₀ of It may be selected from the group consisting of an arylamine group, or Ar ₁ and Ar ₂ may be bonded to each other to form a ring,

   Alkyl, aryl, heteroaryl and arylamine groups of Ar ₁ to Ar ₂ , alkyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkyloxy groups, aryloxy groups, and alkyl groups of R ₁ to R ₄ Silyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group, aryl amine group and the arylene group of L ₁ , hetero arylene group, deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl groups, C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nuclear heterocycloalkyl groups, C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ 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).
2. The method of claim 1,

   R ₁ to R ₄ are identical or different and are each independently selected from the group consisting of an aryl amine of the C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~ C ₆₀ to each other,

   The aryl group, heteroaryl group and arylamine group of R ₁ to R ₄ is deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atom 3 to 40 heterocyclo Alkyl group, C ₆ -C ₆₀ aryl group, nuclear atom 5 to 60 heteroaryl group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, 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 A compound which is substituted or unsubstituted with one or more substituents selected from the group consisting of a pin oxide group and an arylamine group of C ₆ to C ₆₀ , wherein when the substituents are plural, they are the same or different from each other.
3. The method of claim 1,

   Compound represented by the formula (2) is a substituent represented by the following formula (3):

   [Formula 3]

   

   (In Chemical Formula 3,

   L ₁ , Ar ₁ and Ar ₂ are the same as defined in claim 1, respectively.

   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), a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, a heteroaryl group of 5 to 60 nuclear atoms and C ₆ ~ C ₆₀ arylamine group Or may be combined with adjacent substituents to form a condensed aromatic ring or a condensed heteroaromatic ring;

   At this time, the aryl group, heteroaryl group and arylamine group of R ₅ are each independently deuterium, halogen, cyano, C ₁ ~ C ₄₀ alkyl group, C ₃ ~ C ₄₀ cycloalkyl group, heteroatoms of 3 to 40 hetero atoms Cycloalkyl group, C ₆ ~ C ₆₀ aryl group, C ₅ ~ C ₆₀ heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₁ ~ C ₄₀ Alkyl Silyl group, C ₆ ~ C ₆₀ arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ arylphosphine group, C ₆ ~ C ₆₀ aryl Substituted or unsubstituted with one or more substituents selected from the group consisting of phosphine oxide groups and C ₆ -C ₆₀ arylamine groups, provided that the substituents are plural, the same or different from each other).
4. The method of claim 1,

   A compound represented by any one of the following formulas 4-7:

   [Formula 4]

   

   [Formula 5]

   

   [Formula 6]

   

   [Formula 7]

   

   (In Chemical 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 from 0 to 4, b' is an integer from 0 to 2, and c 'is an integer from 0 to 3).
5. The method of claim 1,

   A compound represented by any one of the following formulas (8) to (11):

   [Formula 8]

   

   [Formula 9]

   

   [Formula 10]

   

   [Formula 11]

   

   (In Chemical 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 from 0 to 4, b' is an integer from 0 to 2, b "is an integer from 0 to 1, c 'is an integer from 0 to 3).
6. An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more layers of organic material interposed between the anode and the cathode,

   At least one of the one or more organic material layers comprises the compound according to any one of claims 1 to 5.
7. The method of claim 6,

   The compound is an organic electroluminescent device, characterized in that used as a host of the light emitting layer.
8. The method of claim 6,

   The compound is an organic electroluminescent device, characterized in that used as a hole transport layer material.
9. The method of claim 6,

   The compound is an organic electroluminescent device, characterized in that used as a light emitting auxiliary layer material.