KR20190109881A - Organic light-emitting compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to: a novel compound having excellent electron transporting ability, light emitting ability, and thermal stability; and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, lifespan and the like by comprising the same in one or more organic material layers. The compound according to the present invention can be usefully applied as a material of an organic material layer of the organic electroluminescent device by having excellent thermal stability, electron injection ability/transport ability, light emitting ability and the like.

Description

Organic light-emitting compound and organic electroluminescent device comprising the same {ORGANIC LIGHT-EMITTING COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME}

The present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.

Investigating organic electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965, based on observation of Bernanose's organic thin-film emission, followed by Tang in 1987. ) Is an organic electroluminescent device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer. Since then, in order to make a high efficiency, high-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, 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 materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors. 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. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times compared to the fluorescence, studies on phosphorescent host materials as well as phosphorescent dopants have been conducted.

To date, NPB, BCP, Alq3, and the like are widely known as hole injection layers, hole transport layers, hole blocking layers, and electron transport layer materials, and anthracene derivatives have been reported as emission layer materials. In particular, metal complex compounds containing Ir such as Firpic, Ir (ppy) 3, and (acac) Ir (btp) 2, which have advantages in terms of efficiency improvement among the light emitting layer materials, are blue, green, and red. (red) is used as the phosphorescent dopant material, 4,4-dicarbazolybiphenyl (CBP) is used as the phosphorescent host material.

However, the conventional organic material has an advantageous aspect in terms of light emission characteristics, but the thermal stability is not very good due to the low glass transition temperature, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, development of the organic material layer material which is excellent in performance is calculated | required.

The present invention can be applied to an organic electroluminescent device, and an object of the present invention is to provide a novel organic compound having excellent thermal stability, excellent hole, electron injection and transport ability, and light emitting ability.

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

In order to achieve the above object, the present invention provides a compound represented by the following formula (1).

In Chemical Formula 1,

V, W, Y and Z are the same as or different from each other, and are each independently C (R ₁ ) or N, provided that at least one of the plurality of V, W, Y and Z is N,

L is a single bond or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms,

A is an electron withdrawing group (EWG) represented by any one of the following Formula 1a or 1b,

[Formula 1a]

[Formula 1b]

In Formula 1a or 1b,

* Means a moiety bonded to Formula 1,

A plurality of Xs are the same as or different from each other, and each independently C (R ₁ ) or N, provided that at least one of the plurality of Xs is N,

Ar ₁ and Ar ₂ are the same as or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom It is selected from the group consisting of a heteroaryl group of 5 to 60, and an arylamine group of C ₆ ~ C ₆₀ ,

Wherein a plurality of R ₁ may be the same or different and are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ 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 phosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, C ₆ ~ C ₆₀ Diaryl phosphinyl group and C ₆ ~ C ₆₀ Aryl amine group Or may be combined with other adjacent R ₁ to form a ring;

The arylene group and the heteroarylene group of L and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group and aryloxy group of Ar ₁ to Ar ₂ and R ₁ , Alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ a ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ of the An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, an alkyloxy group of C ₁ to C ₄₀ , an aryloxy group of C ₆ to C ₆₀ , an alkylsilyl group of C ₁ to C ₄₀ , and a C ₆ to C ₆₀ group aryl silyl group, C ₁ ~ C ₄₀ group, the alkyl boron C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphine oxide of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the group, and a C ₆ ~ C ₆₀ aryl It may be substituted with one or more substituent species selected from the group consisting of Min - gi, and wherein when the substituent is plural, they may be the same or different from each other.

In another aspect, the present invention provides a compound represented by the following formula (4).

In Chemical Formula 4,

V, W, Y and Z are the same as or different from each other, and are each independently C (R ₁ ) or N, provided that at least one of the plurality of V, W, Y and Z is N,

L is a single bond or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms,

R ₁ to R ₃ are the same or different and are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ 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 phosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, C ₆ ~ C ₆₀ Diaryl phosphinyl group and C ₆ ~ C ₆₀ Aryl amine group May be selected from, or adjacent R ₁ , R ₂ , or R ₃ may combine to form a ring;

a and b are each independently an integer of 0 to 4,

The arylene group and heteroarylene group of L, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl of R ₁ to R ₃ The group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C ₆ to C ₆₀ aryl group, heteroaryl of nuclear atoms of 5 to 60 aryl group, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₆₀ of the aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ aryl of C ₆₀ silyl group , 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 ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ aryl of C ₆₀ Amine It may be substituted with one or more substituents selected from the group consisting of groups, wherein when there are a plurality of the substituents, they may be the same or different from each other.

In addition, the present invention is an organic electroluminescent device comprising the above-described anode, cathode, and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer is the formula (1) An organic electroluminescent device comprising a compound represented by 4 is provided.

The compound according to the present invention can be usefully applied as an organic material layer material of the organic electroluminescent device because of excellent thermal stability, electron injection ability / transport ability, light emitting ability and the like.

In addition, the organic electroluminescent device of the present invention including the compound in the organic material layer can be effectively applied to a full color display panel because the aspect of light emission performance, driving voltage, lifespan, efficiency, etc. is greatly improved.

Hereinafter, the present invention will be described in detail.

<New organic compound>

The novel organic compound according to the present invention has a spyro-bifluorene-based skeleton containing at least one nitrogen atom (N), and is represented by the formula (1) or (4).

Specifically, the compound represented by the formula (1), the spylo bifluorene containing at least one nitrogen atom as a base skeleton, the spyro skeleton having such EWG characteristics, the linker (L) and the electron absorbing properties It is a structure in which a large electron withdrawing group (EWG) is combined. The compound of Formula 1 may exhibit excellent properties as an electron transport layer (ETL) material because the entire molecule has excellent electron injection and transporting ability.

In addition, the compound represented by the formula (4), spiro bifluorene containing at least one nitrogen atom as a base skeleton, an electron donating group such as a linker (L) and a dibenzo moiety on the base skeleton , EDG). Since the compound of Formula 4 is a spy having EWG properties and a basic skeleton and a dibenzo moiety having EDG properties can be combined with each other to have a bipolar property, the compound of Formula 4 increases the binding force between holes and electrons and narrows ΔEst to provide high efficiency. Luminescent properties are shown. The high triplet energy can improve the luminous efficiency of the device by increasing the number of excitons contributing to the emission in the light emitting layer, and the durability and stability of the device can be improved to effectively increase the life of the device. In particular, the compound of Formula 1 or 4 of the present invention not only has excellent electron injection / transport capacity and high luminous ability, but also has a spyro-cyclic structure, which is excellent in terms of stability of the compound. Accordingly, it is judged to have more excellent thermal stability than the compound having the conventional pyridine-fluorene core structure.

As described above, the compound represented by Chemical Formula 1 or 4 has excellent electron transporting ability and light emission characteristics, and thus any one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, which is an organic material layer of the organic electroluminescent device. It can be used as one material, and preferably used as a material of the light emitting layer of green phosphorescence and red phosphorescence, or an electron transport layer material. Accordingly, the compound represented by Formula 1 or 4 of the present invention is an organic material layer material of the organic EL device, preferably a light emitting layer material (green, red, blue phosphorescent host material), electron transport layer / injection layer material, light emitting auxiliary layer Material, an electron transport auxiliary layer material, more preferably a light emitting layer material, an electron transport layer material, an electron transport auxiliary layer material. The organic electroluminescent device of the present invention including the compound of Formula 1 or 4 can greatly improve performance and lifespan characteristics, and the full color organic light emitting panel to which the organic electroluminescent device is applied can also maximize its performance.

According to the present invention, the compound represented by Formula 1 has spiro bifluorene containing at least one nitrogen atom as a basic skeleton, and a linker (L) and an electron withdrawing group (EWG) are connected to the basic skeleton. .

In Formula 1, the spiro bifluorene-based skeleton includes at least one nitrogen atom (N). Accordingly, it exhibits excellent electron absorbing properties, which is advantageous for electron injection and transport. In one example, V, W, Y and Z of Formula 1 are the same as or different from each other, and each independently C (R ₁ ) or N, at least one of the plurality of V, W, Y and Z may be N. . As a preferred example, N contained in the plurality of V, W, Y and Z may be 1 to 4.

For example, when there is one nitrogen atom included in the spiro bifluorene base skeleton, N is included in one of the rings containing a plurality of V, W, Y and Z. In addition, when there are two nitrogen atoms, one of the rings containing a plurality of V, W, Y and Z contains two N, or two different rings of V, W, Y and Z contain N It can be included one by one. In addition, when there are three nitrogen atoms, each of the three rings containing V, W, Y, and Z includes one N each, or two of the plurality of V, W, Y, and Z one N in one ring. Or two may be included. In addition, in the case of four nitrogen atoms, each of N, each of the rings containing V, W, Y, and Z includes one N, or three of the aforementioned V, W, Y, and Z, two nitrogens, one, It may be included one by one. When the spiro bifluorene-based skeleton according to the present invention contains 1 to 4 nitrogen atoms, a structure in which one nitrogen atom is included in each of the different rings containing a plurality of V, W, Y and Z is preferable. Do. As such, when nitrogen atoms are included in different rings one by one, they have excellent electron transfer characteristics, and thus, low voltage and high efficiency can be driven when used in the host and the electron transport layer.

A plurality of V, W, Y and Z, which are not nitrogen atoms, are each independently C (R ₁ ). Wherein a plurality of R ₁ may be the same or different and are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ 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 phosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, C ₆ ~ C ₆₀ Diaryl phosphinyl group and C ₆ ~ C ₆₀ Aryl amine group It may be selected from, or may be combined with other adjacent R ₁ to form a ring. Specifically, the plurality of R ₁ are each independently selected from the group consisting of hydrogen, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms.

In one embodiment of the present invention, the spyro skeleton including at least one of V, W, Y and Z may be represented by any one of the following structural formulas.

In the above formula, * means a part bonded to the linker (L) of the formula (1) or (4).

L may also be a linker of a conventional divalent group, known in the art. For example, L may be a single bond (eg, a direct bond) or may be selected from the group consisting of C ₆ to C ₁₈ arylene groups and heteroarylene groups having 5 to 18 nuclear atoms.

Specific examples of the L include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyrantrenylene group, a carbazolylene group, a thiophenylene group, an indolylene group, a furinylene group, and quinolinyl And an ethylene group, a pyrrolyylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group and a pyrimidinylene group. More specifically, L is preferably a single bond or a phenylene group, a biphenylene group or a carbazolyl group.

In one embodiment of the present invention, L may be a single bond or a linker selected from the following structures.

In the above formula, * means a part bonded to the linker (L) of the formula (1) or (4). Herein, when L is a fluorene-based linker, two of three * may be freely selected as a binding site.

In Formula 1 of the present invention, the electron attracting group (EWG) connected to the spiro bifluorene-based skeleton is one of a heteroaromatic ring containing at least one nitrogen atom (Formula 1a) and an arylphosphate (Formula 1b). . However, in addition to the above-described formulas (1a) and (1b), it is also within the scope of the present invention to include an electron attractor (EWG) known in the art.

In Formula 1a, a plurality of X's are each independently C (R ₁ ) or N, and at least one of the plurality of X's is N. Preferably it contains 1-3 nitrogen.

In one embodiment of the present invention, the electron withdrawing group (EWG) represented by Formula 1a may be selected from a substituent group represented by Formulas A-1 to A-5.

In A-1 to A-5, R ₁ , Ar ₁ and Ar ₂ are the same as defined in Formula 1 above.

In Formula 1a, when a plurality of X includes 2 to 3, specifically, 3 nitrogen atoms, electron transport properties are excellent, and thus, X is preferable in terms of electron absorption.

Ar ₁ and Ar ₂ are the same as or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom It may be selected from the group consisting of a heteroaryl group of 5 to 60, and an arylamine group of C ₆ ~ C ₆₀ . More specifically, Ar ₁ and Ar ₂ are preferably each independently C ₆ ~ C ₆₀ aryl group and a nuclear atoms aryl of from 5 to 60 heteroaryl group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ . Here, the aryl group and heteroaryl group are each independently C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, Nuclear atom number 3 Heterocycloalkyl group of 40 to 40, aryl group of C ₆ ~ C ₆₀ , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C ₁ ~ C ₄₀ , aryloxy group of C ₆ ~ C ₆₀ , C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ C ₆₀ aryl silyl 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 oxide group, and a C ₆ ~ C ₆₀ aryl amines may be substituted with one or more selected from the group consisting of, wherein if substituted with a plurality of substituents which may be the same or different from each other.

For one embodiment of the present invention, Ar ₁ and Ar ₂ are each independently a group consisting of an aryl group of C ₆ ~ C _{60 and} a heteroaryl group of 5 to 60 nuclear atoms, and an arylamine group of C ₆ ~ C ₆₀ Can be selected from.

According to one embodiment of the present invention, the compound represented by Chemical Formula 1 may be more specifically embodied by any one of the following Chemical Formula 2 or Chemical Formula 3.

In Chemical Formulas 2 to 3,

V, W, X, Y, Z, L, Ar ₁ and Ar ₂ are the same as defined in Chemical Formula 1.

According to a preferred embodiment of the present invention, at least one of the plurality of V, W, Y and Z in the formula (2) or 3 includes a nitrogen atom, specifically of the nitrogen atom contained in the plurality of V, W, Y and Z The number may be 1-4. As such, when the spiro bifluorene-based skeleton contains 1 to 4 nitrogen atoms, a structure in which one nitrogen atom is included in each of a plurality of rings containing a plurality of V, W, Y, and Z is preferable. Do.

In addition, L is a single bond (eg, a direct bond), or is selected from the group consisting of C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms, a plurality of R ₁ are each independently hydrogen , C ₁ ~ C ₄₀ Alkyl group, C ₆ ~ C ₆₀ An aryl group, and a heteroaryl group of 5 to 60 nuclear atoms, Ar ₁ and Ar ₂ are each independently selected from C ₆ ~ C ₆₀ It is preferably selected from the group consisting of an aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and an arylamine group having C ₆ to C ₆₀ .

Compound represented by the formula (4) according to the present invention, the base skeleton is a spiro bifluorene containing at least one nitrogen atom, the linker (L) and the electron donor (EDG) dibenzo-based base skeleton Moieties (eg carbazole groups) are linked.

Here, since V, W, X, Y, Z, and L of Formula 4 overlap with the above-described definition of Formula 1, individual descriptions thereof will be omitted.

In Formula 4, R ₂ and R ₃ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ Aryl group, 5 to 60 heteroaryl group, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group, C ₃ to C ₄₀ alkylsilyl group, C ₆ to C ₆₀ arylsilyl group, C ₁ to C ₄₀ alkylboron group, C ₆ to C ₆₀ arylboron group, C ₆ to C ₆₀ arylphosphanyl group, C ₆ to C ₆₀ monoarylphosphinyl group, C ₆ to C ₆₀ diarylphosphinyl group and C ₆ to C ₆₀ It may be selected from the group consisting of arylamine groups, or adjacent R ₁ , R ₂ , R ₃ may combine with each other to form a ring. Specifically, R ₂ and R ₃ are the same as or different from each other, and each independently composed of hydrogen, an alkyl group of C ₁ to C ₄₀ , an aryl group of C ₆ to C ₆₀ , and a heteroaryl group having 5 to 60 nuclear atoms It is preferably selected from the group.

a and b are each independently an integer of 0-4. Here, when a is 0, R ₂ is hydrogen, and when a is 1 to 4, R ₂ may have the aforementioned substituents except hydrogen. Similarly, when b is 0, R ₃ is hydrogen, and when b is 4, R ₃ may have the aforementioned substituents except hydrogen.

The arylene group and heteroarylene group of L, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl of R ₁ to R ₃ The group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C ₆ to C ₆₀ aryl group, heteroaryl of nuclear atoms of 5 to 60 aryl group, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₆₀ of the aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ aryl of C ₆₀ silyl group , 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 ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ aryl of C ₆₀ Amine It may be substituted with one or more substituents selected from the group consisting of groups, wherein when there are a plurality of the substituents, they may be the same or different from each other.

According to an embodiment of the present invention, the compound represented by Chemical Formula 4 may be more specifically embodied by any one of the following Chemical Formulas 5 to 7.

In Formulas 5 to 7, V, W, Y, Z, L, R ₂ , R ₃ and a are the same as defined in Formula 4, respectively.

Rings B, C and D may be the same or different and each may be a hydrocarbon-based ring containing one or more conventional hydrocarbon-based or heteroatoms known in the art, and they may be combined with other adjacent rings (eg, core structures). It may be in the form of condensation, fusion, crosslinking or spirocyclic.

In one example, rings B, C and D may each be a monocyclic or polycyclic alicyclic ring, a monocyclic or polycyclic heteroalicyclic ring, a monocyclic or polycyclic aromatic ring, or a monocyclic or polycyclic heteroaromatic ring, For example, it may be a monocyclic or polycyclic aromatic ring having 6 to 18 carbon atoms, or a monocyclic or polycyclic heteroaromatic ring having 5 to 18 nuclear atoms. For one embodiment of the present invention, the ring B, C and D ring is preferably an aromatic ring of C ₆ ~ C ₁₈ , or a heteroaromatic ring having 5 to 18 nuclear atoms.

X may be a _{N (Ar 3), O,} S, and C (Ar ₄₎ may be selected from the group consisting of (Ar _5), preferably O or S.

Ar ₃ to Ar ₅ are the same or different and are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ 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 phosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, C ₆ ~ C ₆₀ Diaryl phosphinyl group and C ₆ ~ C ₆₀ Aryl amine group Can be selected from. Specifically, Ar ₃ to Ar ₅ is each independently a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₁₈ It is preferable that the aromatic ring, or 5 to 18 heteroaromatic ring of nuclear atoms.

Here, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group of Ar ₃ to Ar ₅ , Aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₆₀ Aryl group, Nuclear atoms 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₆₀ of the aryloxy group, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ C ₆₀ aryl amine selected from the group consisting of 1 If it may be substituted with one substituent, wherein the substituent of the plurality, they may be the same or different from each other.

According to a preferred embodiment of the present invention, at least one of the plurality of V, W, Y and Z in the formula 5 to 7 includes a nitrogen atom, specifically of the nitrogen atom contained in the plurality of V, W, Y and Z The number may be 1-4. In particular, a structure in which two nitrogen atoms are included in one of the different rings containing a plurality of V, W, Y, and Z is preferable, and in particular, two nitrogen atoms are included in the Z-containing ring into which the dibenzo moiety is introduced. More preferred.

In addition, L is a single bond (eg, a direct bond), or is selected from the group consisting of C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms, a plurality of R ₁ are each independently hydrogen , C ₁ ~ C ₄₀ Alkyl group, C ₆ ~ C ₆₀ Aryl group, and a heteroaryl group of 5 to 60 nuclear atoms, in particular one R ₁ of Z-containing ring is C ₆ ~ C ₆₀ It is preferably an aryl group or a heteroaryl group having 5 to 60 nuclear atoms. Moreover, it is preferable that one of ring B, C, and Z is a phenyl ring or a naphthalene ring.

The compound represented by the general formula (1) or (4) of the present invention described above may be more embodied as a compound represented by any one of the compounds exemplified below, such as A1 to G68. However, the compound represented by the formula (1) or formula (4) of the present invention is not limited by those illustrated below.

"Alkyl" in the present invention means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.

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

In the present invention, "alkynyl" refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.

"Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms combined with a single ring or two or more rings. In addition, a form in which two or more rings are attached to each other (pendant) or condensed may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Heteroaryl" as used herein means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form in which the two or more rings are condensed with an aryl group. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means an alkyl having 1 to 40 carbon atoms, linear, branched or cyclic structure It may include. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

"Arylamine" in the present invention means an amine substituted with aryl having 6 to 40 carbon atoms.

"Cycloalkyl" as used herein means monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

By "heterocycloalkyl" is meant monovalent substituents derived from non-aromatic hydrocarbons having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

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

As used herein, the term “condensed ring” means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

<Organic EL device>

On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the formula (1) or 4 according to the present invention described above.

Specifically, 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 It includes a compound represented by the formula (1) or (4). In this case, the compound may be used alone or in combination of two or more.

The at least one organic material layer may be any one or more of a hole injection layer, a hole transporting layer, a light emitting layer, a light emitting auxiliary layer, an electron transporting layer, an electron transporting auxiliary layer and an electron injection layer, wherein at least one organic material layer is represented by Formula 1 or 4 above. It includes a compound represented. Specifically, the organic material layer including the compound of Formula 1 or 4 is preferably a light emitting layer, an electron transport layer, an electron transport auxiliary layer.

The light emitting layer of the organic electroluminescent device of the present invention may include a host material, and may include the compound of Formula 1 or 4 as the host material. In addition, the light emitting layer of the organic EL device of the present invention may include a compound other than the compound of Formula 1 or 4 as a host.

When the compound represented by Formula 1 or Formula 4 is included as the light emitting layer material of the organic electroluminescent device, preferably blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer is increased. The efficiency (light emitting efficiency and power efficiency), lifetime, luminance and driving voltage of the device can be improved. Specifically, the compound represented by Chemical Formula 1 or 4 is preferably included in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material. In particular, the compound represented by Formula 1 of the present invention is preferably an electron transporting layer material because of excellent electron injection and transport ability, and the compound represented by Formula 4 is preferably a phosphorescent host, a fluorescent host or a dopant material of the light emitting layer, It is preferred that it is a green phosphorescent host.

The structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably a hole transport layer, electron blocking layer, light emission The auxiliary layer may include a compound represented by Chemical Formula 1. Meanwhile, an electron injection layer may be further stacked on the electron transport layer.

The organic electroluminescent device of the present invention may have a structure in which an insulating layer or an adhesive layer is inserted between an electrode and an organic material layer interface.

The organic electroluminescent device of the present invention may be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1 above. have.

The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

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

In addition, the positive electrode material may use any positive electrode material known in the art without limitation. For example, metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals 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 or polyaniline; And carbon black, but are not limited thereto.

In addition, the negative electrode material may use any negative electrode material known in the art without limitation. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.

In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and conventional materials known in the art can be used without limitation.

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

Preparation Example 1

Synthesis of 7'-chlorospiro [fluorene-9,9'-indeno [2,1-b] pyridine]

Anhydrous THF (200 ml) was added to 2-bromo-3- (4-chlorophenyl) pyridine (20.0 g, 74.48 mmol) under a nitrogen stream and stirred at -78 ° C. n-BuLi (2.5M in Hexane, 35.71 ml) was slowly added dropwise into the reactor for 1 hour, and the reaction was carried out with a mixture of 9H-fluoren-9-one (13.42 g, 74.48 mmol) (THF, 100 ml, -78 ° C). ) Was added dropwise to the reactor and stirred at room temperature for 2 hours. Ammonium chloride solution was added to the reaction to terminate the reaction. The organic layer was separated, and sulfuric acid (10 ml) was added dropwise and stirred at 50 ° C. for 5 hours. The resulting solid was filtered with a filter, washed with 1M aqueous sodium hydroxide solution, and filtered to obtain 19 g (75%) of the title compound.

GC-Mass (Theoretical value: 351.84 g / mol, Measured value: 351 g / mol)

1 H-NMR: δ 7.43 (m, 6H), 7.38 (d, 3H), 7.70 (d, 1H), 7.90 (d, 2H), 8.10 (d, 1H), 8.50 (d, 1H)

Preparation Example 2

Synthesis of 7'-chlorospiro [fluorene-9,9'-indeno [2,1-c] pyridine]

반응물로 3-bromo-4-(4-chlorophenyl)pyridine을 사용한 것을 제외하고는, 상기 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 18g (70%)을 얻었다

Except for using 3-bromo-4- (4-chlorophenyl) pyridine as a reaction, the same procedure as in [Preparation Example 1] was performed to obtain the target compound 18g (70%).

GC-Mass (Theoretical value: 351.84 g / mol, Measured value: 351 g / mol)

Preparation Example 3

Synthesis of 7'-chlorospiro [fluorene-9,5'-indeno [1,2-c] pyridine]

Except for using 4-bromo-3- (4-chlorophenyl) pyridine as a reaction, the same procedure as in [Preparation Example 1] was carried out to obtain the target compound 18g (70%).

GC-Mass (Theoretical value: 351.84 g / mol, Measured value: 351 g / mol)

Preparation Example 4

Synthesis of 7'-chlorospiro [fluorene-9,5'-indeno [1,2-b] pyridine]

Except for using 3-bromo-2- (4-chlorophenyl) pyridine as the reaction, the same procedure as in [Preparation Example 1] was carried out to obtain the target compound 20g (75%).

GC-Mass (Theoretical value: 351.84 g / mol, Measured value: 351 g / mol)

Preparation Example 5

Synthesis of 2'-chlorospiro [fluorene-9,9'-indeno [2,1-b] pyridine]

Except for using 5- (2-bromophenyl) -2-chloropyridine as a reaction, the same procedure as in [Preparation Example 1] was carried out to obtain the target compound 20g (75%).

GC-Mass (Theoretical value: 351.84 g / mol, Measured value: 351 g / mol)

Preparation Example 6

Synthesis of 3'-chlorospiro [fluorene-9,5'-indeno [1,2-c] pyridine]

Except for using 5- (2-bromophenyl) -2-chloropyridine as a reaction, the same procedure as in [Preparation Example 1] was carried out to obtain the target compound 20g (75%).

GC-Mass (Theoretical value: 351.84 g / mol, Measured value: 351 g / mol)

Preparation Example 7

Synthesis of 3'-chlorospiro [fluorene-9,5'-indeno [1,2-b] pyridine]

Except for using 2- (2-bromophenyl) -5-chloropyridine as a reaction, the same procedure as in [Preparation Example 1] was carried out to obtain the target compound 17g (65%).

GC-Mass (Theoretical value: 351.84 g / mol, Measured value: 351 g / mol)

Preparation Example 8

Synthesis of 2-chlorospiro [cyclopenta [1,2-b: 4,3-b '] dipyridine-9,9'-fluorene

Except for using 2-bromo-6'-chloro-3,3'-bipyridine as a reaction, the same procedure as in [Preparation Example 1] was carried out to obtain the target compound 15g (60%).

GC-Mass (Theoretical value: 352.82 g / mol, Measured value: 352 g / mol)

Preparation Example 9

Synthesis of 7-chlorospiro [cyclopenta [1,2-b: 3,4-c '] dipyridine-9,9'-fluorene

Except for using 22-bromo-6'-chloro-3,3'-bipyridine as a reaction, the same procedure as in [Preparation Example 1] was carried out to obtain the target compound 17g (65%).

GC-Mass (Theoretical value: 352.82 g / mol, Measured value: 352 g / mol)

Preparation Example 10

Synthesis of 7-chlorospiro [cyclopenta [1,2-b: 3,4-b '] dipyridine-9,9'-fluorene

Except for using 2'-bromo-5-chloro-2,3'-bipyridine as a reaction, the same procedure as in [Preparation Example 1] was carried out to obtain the target compound 17g (65%).

GC-Mass (Theoretical value: 352.82 g / mol, Measured value: 352 g / mol)

Preparation Example 11

Synthesis of 7'-chlorospiro [indeno [2,1-b] pyridine-9,9'-indeno [2,1-c] pyridine]

The same procedure as in [Preparation Example 1] was performed except that 9H-indeno [2,1-b] pyridin-9-one and 2'-bromo-5-chloro-2,3'-bipyridine were used as reactants. The obtained compound 17g (65%) was obtained.

GC-Mass (Theoretical value: 352.82 g / mol, Measured value: 352 g / mol)

Preparation Example 12

Synthesis of 7-chloro-9,9'-spirobi [indeno [2,1-c] pyridine]

Except 9H-indeno [2,1-c] pyridin-9-one and 3-bromo-4- (4-chlorophenyl) pyridine as reactants, the same procedure as in [Preparation Example 1] was performed. Compound 17g (65%) was obtained

GC-Mass (Theoretical value: 352.82 g / mol, Measured value: 352 g / mol)

Preparation Example 13

Synthesis of 7'-chlorospiro [indeno [1,2-c] pyridine-5,9'-indeno [2,1-c] pyridine]

Except that 5H-indeno [1,2-c] pyridin-5-one and 3-bromo-4- (4-chlorophenyl) pyridine were used as reactants, the same procedure as in [Preparation Example 1] was performed. Compound 17g (65%) was obtained.

GC-Mass (Theoretical value: 352.82 g / mol, Measured value: 352 g / mol)

Preparation Example 14

Synthesis of 7'-chlorospiro [indeno [1,2-c] pyridine-5,9'-indeno [2,1-c] pyridine]

Except that 5H-indeno [1,2-b] pyridin-5-one and 3-bromo-4- (4-chlorophenyl) pyridine were used as reactants, the same procedure as in [Preparation Example 1] was performed. Compound 18g (70%) was obtained.

GC-Mass (Theoretical value: 352.82 g / mol, Measured value: 352 g / mol)

Preparation Example 15

Synthesis of 8-chlorospiro [indeno [1,2-b] pyridine-5,9'-indeno [2,1-b] pyridine]

Except 9H-indeno [2,1-b] pyridin-9-one and 3-bromo-4- (3-chlorophenyl) pyridine as reactants, the same procedure as in [Preparation Example 1] was performed. Compound 18g (70%) was obtained

GC-Mass (Theoretical value: 352.82 g / mol, Measured value: 352 g / mol)

Preparation Example 16

Synthesis of 8-chlorospiro [indeno [1,2-b] pyridine-5,9'-indeno [2,1-c] pyridine]

Except 9H-indeno [2,1-c] pyridin-9-one and 3-bromo-4- (3-chlorophenyl) pyridine as reactants, the same procedure as in [Preparation Example 1] was performed. Compound 18g (70%) was obtained.

GC-Mass (Theoretical value: 352.82 g / mol, Measured value: 352 g / mol)

Preparation 17

Synthesis of 8-chlorospiro [indeno [1,2-b] pyridine-5,5'-indeno [1,2-c] pyridine]

반응물로 5H-indeno[1,2-c]pyridin-5-one과 3-bromo-4-(3-chlorophenyl)pyridine을 사용한 것을 제외하고는, 상기 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 19g (75%)을 얻었다

Except that 5H-indeno [1,2-c] pyridin-5-one and 3-bromo-4- (3-chlorophenyl) pyridine were used as reactants, the same procedure as in [Preparation Example 1] was performed. Compound 19g (75%) was obtained

GC-Mass (Theoretical value: 352.82 g / mol, Measured value: 352 g / mol)

Preparation 18

Synthesis of 8-chloro-5,5'-spirobi [indeno [1,2-b] pyridine]

Except that 5H-indeno [1,2-b] pyridin-5-one and 3-bromo-4- (3-chlorophenyl) pyridine were used as reactants, the same procedure as in [Preparation Example 1] was performed. 19 g (75%) of compound was obtained.

GC-Mass (Theoretical value: 352.82 g / mol, Measured value: 352 g / mol)

Preparation Example 19

Synthesis of 1-chlorospiro [cyclopenta [2,1-c: 3,4-c '] dipyridine-5,9'-fluorene

반응물로 4'-bromo-2-chloro-3,3'-bipyridine을 사용한 것을 제외하고는, 상기 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 19g (75%)을 얻었다.

19g (75%) of the title compound was obtained in the same manner as in [Preparation Example 1], except that 4'-bromo-2-chloro-3,3'-bipyridine was used as a reaction.

GC-Mass (Theoretical value: 352.82 g / mol, Measured value: 352 g / mol)

Preparation Example 20

Synthesis of 1'-chlorospiro [cyclopenta [2,1-b: 3,4-b '] dipyridine-5,5'-cyclopenta [2,1-c: 3,4-c'] dipyridine]

The preparations described above were performed except that 5H-cyclopenta [2,1-b: 3,4-b '] dipyridin-5-one and 4'-bromo-2-chloro-3,3'-bipyridine were used as reactants. Example 1] was carried out to obtain the target compound 18g (70%).

GC-Mass (Theoretical value: 354.80 g / mol, Measured value: 354 g / mol)

Preparation Example 21

Synthesis of 4-chlorospiro [cyclopenta [1,2-b: 3,4-b '] dipyridine-9,5'-cyclopenta [2,1-b: 3,4-b'] dipyridine]

The preparations described above were performed except that 5H-cyclopenta [2,1-b: 3,4-b '] dipyridin-5-one and 3-bromo-4'-chloro-2,3'-bipyridine were used as reactants. Example 1] was carried out to obtain the target compound 18g (70%).

GC-Mass (Theoretical value: 354.80 g / mol, Measured value: 354 g / mol)

Preparation Example 22

Synthesis of 9'-chlorospiro [cyclopenta [2,1-b: 3,4-b '] dipyridine-5,5'-cyclopenta [2,1-b: 4,3-c'] dipyridine]

[Preparation of the above preparation except that 5H-cyclopenta [2,1-b: 3,4-b '] dipyridin-5-one and 3-bromo-3'-chloro-2,4'-bipyridine were used as reactants. Example 1] was carried out to obtain the target compound 17g (65%).

GC-Mass (Theoretical value: 354.80 g / mol, Measured value: 354 g / mol)

Preparation 23

Synthesis of 9'-chlorospiro [cyclopenta [2,1-b: 3,4-b '] dipyridine-5,5'-cyclopenta [2,1-b: 4,3-c'] dipyridine]

[Preparation of the above preparation except that 5H-cyclopenta [2,1-b: 3,4-b '] dipyridin-5-one and 3-bromo-3'-chloro-2,4'-bipyridine were used as reactants. Example 1] was carried out to obtain the target compound 17g (65%).

GC-Mass (Theoretical value: 354.80 g / mol, Measured value: 354 g / mol)

Preparation 24

Synthesis of 9'-chlorospiro [cyclopenta [2,1-b: 3,4-b '] dipyridine-5,5'-cyclopenta [2,1-b: 3,4-c'] dipyridine]

The preparations described above were performed except that 5H-cyclopenta [2,1-b: 3,4-b '] dipyridin-5-one and 3-bromo-2'-chloro-2,3'-bipyridine were used as reactants. Example 1] was carried out to obtain the target compound 18g (70%).

GC-Mass (Theoretical value: 354.80 g / mol, Measured value: 354 g / mol)

Preparation 25

Synthesis of 2'-chloro-3'-phenylspiro [fluorene-9,9'-indeno [1,2-b] pyrazine]

Except for using 2,6-dichloro-3,5-diphenylpyrazine as a reaction, the same procedure as in [Preparation Example 1] was carried out to obtain the target compound 22g (70%).

GC-Mass (Theoretical value: 428.92 g / mol, Measured value: 428 g / mol)

Preparation 26

Synthesis of 3'-chloro-2'-phenylspiro [fluorene-9,9'-indeno [1,2-b] pyrazine]

Except for using 2,5-dichloro-3,6-diphenylpyrazine as a reaction, the same procedure as in [Preparation Example 1] was carried out to obtain the target compound 20g (65%).

GC-Mass (Theoretical value: 428.92 g / mol, Measured value: 428 g / mol)

Preparation Example 27

Synthesis of 2'-chlorospiro [cyclopenta [2,1-b: 3,4-b '] dipyridine-5,9'-fluorene

Prepared as described above, except that 5H-cyclopenta [2,1-b: 3,4-b '] dipyridin-5-one and 2-bromo-4'-chloro-1,1'-biphenyl were used as reactants. Example 1] was carried out to obtain the target compound 20g (65%).

GC-Mass (Theoretical value: 352.82 g / mol, Measured value: 352 g / mol)

Preparation Example 28

Synthesis of 3'-chlorospiro [cyclopenta [2,1-b: 3,4-b '] dipyridine-5,9'-fluorene

Prepared as described above, except that 5H-cyclopenta [2,1-b: 3,4-b '] dipyridin-5-one and 2-bromo-3'-chloro-1,1'-biphenyl were used as reactants. Example 1] was carried out to obtain the target compound 18g (70%).

GC-Mass (Theoretical value: 352.82 g / mol, Measured value: 352 g / mol)

Preparation Example 29

Synthesis of 4'-chlorospiro [cyclopenta [2,1-b: 3,4-b '] dipyridine-5,9'-fluorene

Prepared as described above, except that 5H-cyclopenta [2,1-b: 3,4-b '] dipyridin-5-one and 2-bromo-2'-chloro-1,1'-biphenyl were used as reactants. Example 1] was carried out to obtain the target compound 18g (70%).

GC-Mass (Theoretical value: 352.82 g / mol, Measured value: 352 g / mol)

Synthesis Example 1

Synthesis of A1

7 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) spiro [fluorene-9,9'-indeno [2,1-b] pyridine] (10.0) under nitrogen stream g, 22.20 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.02 g, 22.50 mmol), Pd (PPh ₃ ) ₄ (0.78 g, 0.68 mmol), K ₂ CO ₃ ( 9.33 g, 67.51 mmol), 100 ml of 1,4-dioxane and 25 ml of H ₂ O were mixed and stirred at 100 ° C. for 4 hours. After completion of the reaction, the mixture was extracted with dichloromethane, MgSO ₄ was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound 9 g (yield: 75%) by using column chromatography.

GC-Mass (Theoretical value: 548.65 g / mol, Measured value: 548 g / mol)

Synthesis Example 2

Synthesis of A2

Except for using Compound-2 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, the same procedure as in Synthesis Example 1 was carried out to give 10 g (yield: 70%) of the target compound. Obtained.

GC-Mass (Theoretical value: 638.73 g / mol, Measured value: 638 g / mol)

Synthesis Example 3

Synthesis of A11

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 10 g (yield: 70%) of the target compound.

GC-Mass (Theoretical value: 654.79 g / mol, Measured value: 654 g / mol)

Synthesis Example 4

Synthesis of A12

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 10 g (yield: 70%) of the target compound.

GC-Mass (Theoretical value: 654.79 g / mol, Measured value: 654 g / mol)

Synthesis Example 5

Synthesis of A21

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same process as in Synthesis Example 1 was carried out to obtain the target compound 8 g (yield: 65%).

GC-Mass (Theoretical value: 598.67 g / mol, Measured value: 598 g / mol)

Synthesis Example 6

Synthesis of A22

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same process as in Synthesis Example 1 was carried out to obtain the target compound 9 g (yield: 70%).

GC-Mass (Theoretical value: 598.71 g / mol, Measured value: 598 g / mol)

Synthesis Example 7

Synthesis of A31

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain the target compound 12 g (yield: 75%).

GC-Mass (Theoretical value: 713.84 g / mol, Measured value: 713 g / mol)

Synthesis Example 8

Synthesis of A32

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same process as in Synthesis Example 1 was carried out to obtain the target compound 8 g (yield: 75%).

GC-Mass (Theoretical value: 517.57 g / mol, Measured value: 517 g / mol)

Synthesis Example 9

Synthesis of A33

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same process as in Synthesis Example 1 was carried out to obtain the target compound 8 g (yield: 75%).

GC-Mass (Theoretical value: 548.65 g / mol, Measured value: 548 g / mol)

Synthesis Example 10

Synthesis of A34

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 10 g (yield: 70%) of the target compound.

GC-Mass (Theoretical value: 638.73 g / mol, Measured value: 638 g / mol)

Synthesis Example 11

Synthesis of A43

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 11 g (yield: 75%) of the target compound.

GC-Mass (Theoretical value: 654.79 g / mol, Measured value: 654 g / mol)

Synthesis Example 12

Synthesis of A44

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 10 g (yield: 75%) of the target compound.

GC-Mass (Theoretical value: 623.76 g / mol, Measured value: 623 g / mol)

Synthesis Example 13

Synthesis of A53

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same process as in Synthesis Example 1 was carried out to obtain the target compound 9 g (yield: 70%).

GC-Mass (Theoretical value: 598.67 g / mol, Measured value: 598 g / mol)

Synthesis Example 14

Synthesis of A54

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 10 g (yield: 75%) of the target compound.

GC-Mass (Theoretical value: 598.71 g / mol, Measured value: 598 g / mol)

Synthesis Example 15

Synthesis of A65

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same process as in Synthesis Example 1 was carried out to obtain the target compound 9 g (yield: 80%).

GC-Mass (Theoretical value: 549.64 g / mol, Measured value: 549 g / mol)

Synthesis Example 16

Synthesis of A66

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 10 g (yield: 75%) of the target compound.

GC-Mass (Theoretical value: 639.72 g / mol, Measured value: 639 g / mol)

Synthesis Example 17

Synthesis of A77

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain the target compound 10 g (yield: 80%).

GC-Mass (Theoretical value: 599.66 g / mol, Measured value: 599 g / mol)

Synthesis Example 18

Synthesis of A78

Except for using Compound-1 and Compound-2 of the above reaction scheme was carried out the same process as in Synthesis Example 1 to obtain the target compound 10 g (yield: 80%).

GC-Mass (Theoretical value: 599.70 g / mol, Measured value: 599 g / mol)

Synthesis Example 19

Synthesis of A81

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain the target compound 10 g (yield: 80%).

GC-Mass (Theoretical value: 549.64 g / mol, Measured value: 549 g / mol)

Synthesis Example 20

Synthesis of A82

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 10 g (yield: 75%) of the target compound.

GC-Mass (Theoretical value: 639.72 g / mol, Measured value: 639 g / mol)

Synthesis Example 21

Synthesis of B49

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same process as in Synthesis Example 1 was carried out to obtain the target compound 9 g (yield: 75%).

GC-Mass (Theoretical value: 549.64 g / mol, Measured value: 549 g / mol)

Synthesis Example 22

Synthesis of B50

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was performed to obtain 11 g (yield: 80%) of the target compound.

GC-Mass (Theoretical value: 639.72 g / mol, Measured value: 639 g / mol)

Synthesis Example 23

Synthesis of B55

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 11 g (yield: 70%) of the target compound.

GC-Mass (Theoretical value: 714.83 g / mol, Measured value: 714 g / mol)

Synthesis Example 24

Synthesis of B56

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same process as in Synthesis Example 1 was carried out to obtain the target compound 8 g (yield: 70%).

GC-Mass (Theoretical value: 518.56 g / mol, Measured value: 518 g / mol)

Synthesis Example 25

Synthesis of B57

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same process as in Synthesis Example 1 was carried out to obtain the target compound 9 g (yield: 75%).

GC-Mass (Theoretical value: 549.64 g / mol, Measured value: 549 g / mol)

Synthesis Example 26

Synthesis of B58

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 10 g (yield: 75%) of the target compound.

GC-Mass (Theoretical value: 639.72 g / mol, Measured value: 639 g / mol)

Synthesis Example 27

Synthesis of B69

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain the target compound 8 g (yield: 60%).

GC-Mass (Theoretical value: 599.66 g / mol, Measured value: 599 g / mol)

Synthesis Example 28

Synthesis of B70

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain the target compound 8 g (yield: 60%).

GC-Mass (Theoretical value: 599.70 g / mol, Measured value: 599 g / mol)

Synthesis Example 29

Synthesis of D105

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was performed to obtain 11 g (yield: 80%) of the target compound.

GC-Mass (Theoretical value: 625.74 g / mol, Measured value: 625 g / mol)

Synthesis Example 30

Synthesis of D106

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain the target compound 10 g (yield: 65%).

GC-Mass (Theoretical value: 715.82 g / mol, Measured value: 715 g / mol)

Synthesis Example 31

Synthesis of D115

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 11 g (yield: 70%) of the target compound.

GC-Mass (Theoretical value: 731.88 g / mol, Measured value: 731 g / mol)

Synthesis Example 32

Synthesis of D116

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 11 g (yield: 70%) of the target compound.

GC-Mass (Theoretical value: 700.85 g / mol, Measured value: 700 g / mol)

Synthesis Example 33

Synthesis of D125

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 11 g (yield: 75%) of the target compound.

GC-Mass (Theoretical value: 675.76 g / mol, Measured value: 675 g / mol)

Synthesis Example 34

Synthesis of D126

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 12 g (yield: 80%) of the target compound.

GC-Mass (Theoretical value: 675.80 g / mol, Measured value: 675 g / mol)

Synthesis Example 35

Synthesis of D135

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was performed to obtain 14 g (yield: 84%) of the target compound.

GC-Mass (Theoretical value: 790.93 g / mol, Measured value: 790 g / mol)

Synthesis Example 36

Synthesis of D136

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 11 g (yield: 86%) of the target compound.

GC-Mass (Theoretical value: 594.65 g / mol, Measured value: 594 g / mol)

Synthesis Example 37

Synthesis of D136

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 11 g (yield: 86%) of the target compound.

GC-Mass (Theoretical value: 594.65 g / mol, Measured value: 594 g / mol)

Synthesis Example 38

Synthesis of F1

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 11 g (yield: 75%) of the target compound.

GC-Mass (Theoretical value: 701.83 g / mol, Measured value: 701 g / mol)

Synthesis Example 39

Synthesis of F2

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 12 g (yield: 70%) of the target compound.

GC-Mass (Theoretical value: 791.91 g / mol, Measured value: 791 g / mol)

Synthesis Example 40

Synthesis of F4

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 13 g (yield: 78%) of the target compound.

GC-Mass (Theoretical value: 776.94 g / mol, Measured value: 776 g / mol)

Synthesis Example 41

Synthesis of F8

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain the target compound 12 g (yield: 72%).

GC-Mass (Theoretical value: 746.85 g / mol, Measured value: 746 g / mol)

Synthesis Example 42

Synthesis of F128

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 12 g (yield: 80%) of the target compound.

GC-Mass (Theoretical value: 703.81 g / mol, Measured value: 703 g / mol)

Synthesis Example 43

Synthesis of F132

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was performed to obtain 14 g (yield: 82%) of the target compound.

GC-Mass (Theoretical value: 778.92 g / mol, Measured value: 778 g / mol)

Synthesis Example 44

Synthesis of F140

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was performed to obtain 14 g (yield: 82%) of the target compound.

GC-Mass (Theoretical value: 778.92 g / mol, Measured value: 778 g / mol)

Synthesis Example 45

Synthesis of F141

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same process as in Synthesis Example 1 was carried out to obtain 13 g (yield: 80%) of the target compound.

GC-Mass (Theoretical value: 753.83 g / mol, Measured value: 753 g / mol)

Synthesis Example 46

Synthesis of F145

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 11 g (yield: 75%) of the target compound.

GC-Mass (Theoretical value: 703.81 g / mol, Measured value: 703 g / mol)

Synthesis Example 47

Synthesis of F146

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was performed to obtain 13 g (yield: 77%) of the target compound.

GC-Mass (Theoretical value: 793.89 g / mol, Measured value: 793 g / mol)

Synthesis Example 48

Synthesis of F159

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 12 g (yield: 70%) of the target compound.

GC-Mass (Theoretical value: 778.88 g / mol, Measured value: 778 g / mol)

Synthesis Example 49

Synthesis of F160

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain the target compound 12 g (yield: 72%).

GC-Mass (Theoretical value: 748.83 g / mol, Measured value: 748 g / mol)

Synthesis Example 50

Synthesis of G38

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 10 g (yield: 75%) of the target compound.

GC-Mass (Theoretical value: 639.72 g / mol, Measured value: 639 g / mol)

Synthesis Example 51

Synthesis of G48

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 11 g (yield: 75%) of the target compound.

GC-Mass (Theoretical value: 700.85 g / mol, Measured value: 701 g / mol)

Synthesis Example 52

Synthesis of G56

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 12 g (yield: 80%) of the target compound.

GC-Mass (Theoretical value: 700.85 g / mol, Measured value: 701 g / mol)

Synthesis Example 53

Synthesis of G1

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was performed to obtain 11 g (yield: 80%) of the target compound.

GC-Mass (Theoretical value: 701.83 g / mol, Measured value: 701 g / mol)

Synthesis Example 54

Synthesis of G2

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 14 g (yield: 85%) of the target compound.

GC-Mass (Theoretical value: 791.91 g / mol, Measured value: 791 g / mol)

Synthesis Example 55

Synthesis of G7

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 12 g (yield: 73%) of the target compound.

GC-Mass (Theoretical value: 790.93 g / mol, Measured value: 790 g / mol)

Synthesis Example 56

Synthesis of G22

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain the target compound 12 g (yield: 75%).

GC-Mass (Theoretical value: 751.89 g / mol, Measured value: 751 g / mol)

Synthesis Example 57

Synthesis of G20

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same process as in Synthesis Example 1 was carried out to obtain 13 g (yield: 80%) of the target compound.

GC-Mass (Theoretical value: 776.94 g / mol, Measured value: 776 g / mol)

Synthesis Example 58

Synthesis of G15

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 14 g (yield: 85%) of the target compound.

GC-Mass (Theoretical value: 775.91 g / mol, Measured value: 775 g / mol)

Synthesis Example 59

Synthesis of G16

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 11 g (yield: 75%) of the target compound.

GC-Mass (Theoretical value: 715.87 g / mol, Measured value: 715 g / mol)

Synthesis Example 60

Synthesis of G26

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain 12 g (yield: 70%) of the target compound.

GC-Mass (Theoretical value: 851.03 g / mol, Measured value: 851 g / mol)

Synthesis Example 61

Synthesis of G27

Except for using Compound-1 and Compound-2 of the above-described scheme, 13 g (yield: 75%) of the target compound was obtained in the same manner as in Synthesis Example 1.

GC-Mass (Theoretical value: 851.03 g / mol, Measured value: 851 g / mol)

Synthesis Example 62

Synthesis of G29

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was carried out to obtain the target compound 10 g (yield: 72%).

GC-Mass (Theoretical value: 715.87 g / mol, Measured value: 715 g / mol)

Synthesis Example 63

Synthesis of G31

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same procedure as in Synthesis Example 1 was performed to obtain 11 g (yield: 80%) of the target compound.

GC-Mass (Theoretical value: 699.81 g / mol, Measured value: 699 g / mol)

Synthesis Example 64

Synthesis of G32

Except for using Compound-1 and Compound-2 of the above reaction scheme, the same process as in Synthesis Example 1 was carried out to obtain 10 g (yield: 78%) of the target compound.

GC-Mass (Theoretical value: 6 g / mol, Measured value: 639 g / mol)

Example A-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 with distilled water, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and drying was carried out, and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and the substrate was cleaned for 5 minutes using UV. The substrate was then transferred to a vacuum depositor.

Organic EL on DS-205 (80 nm) / NPB (15 nm) / ADN + 5% DS-405 (30 nm) / A1 (80 nm) / LiF (1 nm) / Al (200 nm) in order on the prepared ITO transparent electrode The device was manufactured.

Example A-2 to A-36 Fabrication of Organic EL Device

An organic EL device was manufactured in the same manner as in Example 1, except that the compound (eg, A2 to G20) of Table 1 below was used as the electron transporting material, instead of the compound A1 used as the electron transporting material in Example A-1. Prepared.

[Comparative Examples 1 to 3] Fabrication of Organic EL Device

An organic EL device was manufactured in the same manner as in Example A-1, except that Alq3, Y1, and Z1 were used as the electron transporting material, instead of the compound A1 used as the electron transporting material in Example A-1.

For reference, DS-205 and DS-405 used in the device fabrication are products of Doosan Electronics BG, and the structures of NPB, AND, Alq3, Y1, and Z1 are as follows.

[ Evaluation example  One]

The driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured for the organic EL devices manufactured in Examples A-1 to A-36 and Comparative Examples 1 to 3, respectively, and the results are shown in Table 1 below. .

Sample Electron transport layer Drive voltage (V) Current efficiency (cd / A) Example A-1 A1 3.3 8.2 Example A-2 A2 3.7 8.5 Example A-3 A11 3.5 7.2 Example A-4 A12 3.5 8.8 Example A-5 A21 3.7 9.1 Example A-6 A31 3.8 8.5 Example A-7 A32 3.6 8.5 Example A-8 A33 3.8 7.8 Example A-9 A44 3.9 7.9 Example A-10 A53 3.6 8.2 Example A-11 A54 3.3 8.1 Example A-12 A65 3.9 7.9 Example A-13 A78 3.6 8.2 Example A-14 A81 3.9 7.9 Example A-15 B49 3.6 8.2 Example A-16 B56 3.3 8.1 Example A-17 B57 3.9 7.9 Example A-18 B69 3.6 8.2 Example A-19 B70 3.3 8.1 Example A-20 D116 3.9 7.9 Example A-21 F1 3.6 8.2 Example A-22 F2 3.3 8.1 Example A-23 F4 3.9 7.9 Example A-24 F8 3.6 8.2 Example A-25 F129 3.9 7.9 Example A-26 F132 3.3 8.1 Example A-27 F140 3.9 7.9 Example A-28 F141 3.6 8.2 Example A-29 F145 3.3 8.1 Example A-30 F146 3.9 7.9 Example A-31 F159 3.6 8.2 Example A-32 F160 3.9 7.9 Example A-33 G48 3.3 8.1 Example A-34 G56 3.9 7.9 Example A-35 G1 3.6 8.2 Example A-36 G20 3.3 8.1 Comparative Example 1 Alq ₃ 4.7 5.6 Comparative Example 2 Y1 4.3 6.2 Comparative Example 3 Z1 4.4 6.5

As shown in Table 1, the organic EL devices (Examples A-1 to A-36) using the compound according to the present invention as the electron transporting layer are aryl as Comparative Example 1 using the conventional Alq3 and the electron attracting group (EWG). It was found that the organic EL device of Comparative Examples 2 to 3 introduced with the group exhibited better performance in terms of current efficiency and driving voltage.

[ Example  B-1] Green Organic Electric field  Manufacture of light emitting device

Synthesized Compound A1 was subjected to high purity sublimation purification by a conventionally known method, and then 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, Hwasin 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) / A1 (40 nm) + 10% Ir (ppy) 3 / BCP (10 nm) / Alq 3 (30 nm) / LiF ( 1 nm) / Al (200 nm) was laminated in order to manufacture an organic EL device.

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

Example B-2 to B-30 Fabrication of Green Organic Electroluminescent Device

An organic EL material was manufactured in the same manner as in Example B-1, except that the compound shown in Table 2 (eg, A2 to G22) was used instead of the compound A1 used as the green light emitting material in Example B-1. The device was manufactured.

[ Comparative example  4 ~ 6] green organic Electric field  Manufacture of light emitting device

A green organic electroluminescent device was manufactured in the same manner as in Example B-1, except that CBP, Y1, and Z1 were used instead of Compound A1 in Example B-1.

[ Evaluation example  2]

For the green organic electroluminescent devices manufactured in Examples B-1 to B-30 and Comparative Examples 4 to 6, respectively, driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured, and as a result, Is shown in Table 2 below.

Sample Green light emitting layer Drive voltage (V) Current efficiency (cd / A) Example B-1 A1 6.7 41.9 Example B-2 A2 6.85 42.1 Example B-3 A11 6.8 44.8 Example B-4 A22 6.8 47.5 Example B-5 A31 6.85 41.5 Example B-6 A32 6.65 41.9 Example B-7 A33 6.01 42.4 Example B-8 A34 6.8 42.3 Example B-9 A43 6.9 45.2 Example B-10 A53 6.8 44.6 Example B-11 A54 6.7 44.1 Example B-12 A65 6.65 43.6 Example B-13 A66 6.7 42.6 Example B-14 A77 6.9 44.1 Example B-15 A78 6.8 42.8 Example B-16 A81 6.7 41.4 Example B-17 A82 6.7 41.8 Example B-18 B49 6.65 45.3 Example B-19 D105 6.65 42.6 Example B-20 D106 6.7 41.8 Example B-21 D115 6.65 45.3 Example B-22 D125 6.7 45.1 Example B-23 D126 6.8 42.8 Example B-24 D135 6.7 41.4 Example B-25 D136 6.7 41.8 Example B-26 G38 6.65 45.3 Example B-27 G1 6.7 45.1 Example B-28 G2 6.65 42.6 Example B-29 G7 6.7 41.8 Example B-30 G22 6.65 45.3 Comparative Example 4 CBP 7.05 36.2 Comparative Example 5 Y1 6.93 38.2 Comparative Example 6 Z1 6.95 38.5

As shown in Table 2 above, the green organic electroluminescent devices (Examples B-1 to B-30) using the compound according to the present invention as a light emitting material are compared with Comparative Example 4 using only CBP as a material for the light emitting layer. It was found that the green organic electroluminescent device of Comparative Examples 5 to 6 in which an aryl group was introduced as the group (EWG) showed better performance in terms of current efficiency and driving voltage.

[ Example  C-1] red organic Electric field  Manufacture of light emitting device

Synthesized Compound G10 was a high purity sublimation tablet using 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 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then the substrate is cleaned for 5 minutes by UV and vacuum evaporator The substrate was transferred to.

On the prepared ITO transparent electrode, m-MTDATA (60 nm) / TCTA (80 nm) / G10 (40 nm) + 10% (piq) 2Ir (acac) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to prepare an organic EL device.

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

[ Example  C-2 ~ C-10] Red Organic Electric field  Manufacturing of Light Emitting Device]

Example C-1 except that the material shown in Table 3 (eg, G15, G16, G27, G29, G31 to G32) was used instead of the compound G10 used as the red light emitting material in forming the red light emitting layer in Example C-1. The organic EL device was fabricated in the same manner as -1.

Comparative Example 7 Fabrication of Red Organic Electroluminescent Device

A red organic electroluminescent device was manufactured in the same manner as in Example C-1, except that CBP was used instead of Compound G10 in Example C-1.

[Evaluation Example 3]

The driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured for each of the red organic electroluminescent devices fabricated in Examples C-1 to C-7 and Comparative Example 7, and the results are shown in Table 3 below. It was.

Sample Red light emitting layer Drive voltage (V) Current efficiency (cd / A) Example C-1 G10 4.9 11.9 Example C-2 G15 4.2 11.5 Example C-3 G16 4.7 11.9 Example C-4 G27 5 12.4 Example C-5 G29 4.1 12.3 Example C-6 G31 4.2 11.5 Example C-7 G32 4.7 11.9 Comparative Example 7 CBP 5.2 8.2

As shown in Table 3, the red organic electroluminescent devices (Examples C-1 to C-7) using the compound according to the present invention as a light emitting material, the red organic of Comparative Example 7 using only conventional CBP as a material of the light emitting layer It was found that the electroluminescent device exhibited better performance in terms of current efficiency and driving voltage.

[ Example  D-1] blue organic Electric field  Manufacture of light emitting device

Synthesized Compound A1 was subjected to high purity sublimation purification by a conventionally known method, and then a blue 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 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then the substrate is cleaned for 5 minutes by UV and vacuum evaporator The substrate was transferred to.

On the ITO transparent electrode prepared as above, DS-205 (Doosan Co., Ltd.) (80 nm) / NPB (15 nm) / A1 (40 nm) + 5% DS-405 (Doosan Co.) / BCP (10 nm) / Alq3 ( 30 nm) / LiF (1 nm) / Al (200 nm) was laminated to prepare an organic EL device.

The structure of ADN used is as follows.

Example D-2 to D-10 Fabrication of Blue Organic Electroluminescent Devices

In Example D-1 except for using the compound of Table 4 (for example, A21 ~ A82) instead of the compound A1 used as the blue light emitting material in the formation of the blue light emitting layer, it was carried out in the same manner as in Example D-1 An EL device was manufactured.

Comparative Example 8 Fabrication of Blue Organic Electroluminescent Device

A blue organic electroluminescent device was manufactured in the same manner as in Example D-1, except that ADN was used instead of A1 in Example D-1.

[ Evaluation example  4]

For each of the blue organic electroluminescent devices fabricated in Examples D-1 to D-10 and Comparative Example 8, the driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured, and the results are shown in Table 4 below. It was.

Sample Blue light emitting layer Driving voltage
(V) Current efficiency
(cd / A) Example D-1 A1 4.3 9.2 Example D-2 A21 4.5 7.1 Example D-3 A32 4.6 8.3 Example D-4 A33 4.2 9.6 Example D-5 A34 4.7 6.5 Example D-6 A53 4 7.1 Example D-7 A65 4.5 8.6 Example D-8 A66 4.3 7.5 Example D-9 A81 4.4 7.6 Example D-10 A82 4.6 8.6 Comparative Example 8 ADN 5.6 4.8

As shown in Table 4, the blue organic electroluminescent devices (Examples D-1 to D-10) using the compound according to the present invention as a light emitting material, the blue organic of Comparative Example 8 using only ADN as a material of the light emitting layer It was found that the electroluminescent device exhibited better performance in terms of current efficiency and driving voltage.

Claims (11)

Compound represented by the following formula (1):
[Formula 1]

In Chemical Formula 1,
V, W, Y and Z are the same as or different from each other, and are each independently C (R ₁ ) or N, provided that at least one of the plurality of V, W, Y and Z is N,
L is a single bond or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
A is an electron withdrawing group (EWG) represented by any one of the following Formula 1a or 1b,
[Formula 1a]

[Formula 1b]

In Formula 1a or 1b,
* Means a moiety bonded to Formula 1,
A plurality of Xs are the same as or different from each other, and each independently C (R ₁ ) or N, provided that at least one of the plurality of Xs is N,
Ar ₁ and Ar ₂ are the same as or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, nuclear atom It is selected from the group consisting of a heteroaryl group of 5 to 60, and an arylamine group of C ₆ ~ C ₆₀ ,
Wherein a plurality of R ₁ may be the same or different and are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ 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 phosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, C ₆ ~ C ₆₀ Diaryl phosphinyl group and C ₆ ~ C ₆₀ Aryl amine group Or may be combined with other adjacent R ₁ to form a ring;
The arylene group and the heteroarylene group of L and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group and aryloxy group of Ar ₁ to Ar ₂ and R ₁ , Alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ a ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ of the An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, an alkyloxy group of C ₁ to C ₄₀ , an aryloxy group of C ₆ to C ₆₀ , an alkylsilyl group of C ₁ to C ₄₀ , and a C ₆ to C ₆₀ group aryl silyl group, C ₁ ~ C ₄₀ group, the alkyl boron C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphine oxide of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the group, and a C ₆ ~ C ₆₀ aryl It may be substituted with one or more substituent species selected from the group consisting of Min - gi, and wherein when the substituent is plural, they may be the same or different from each other. The method of claim 1,
The electron withdrawing group represented by Chemical Formula 1a is selected from the group of substituents represented by the following Chemical Formulas A-1 to A-5:

In the above A-1 to A-5,
R ₁ , Ar ₁ and Ar ₂ are each as defined in claim 1. The method of claim 1,
Ar ₁ and Ar ₂ are each independently selected from the group consisting of a C ₆ ~ C ₆₀ aryl group and the number of nuclear atoms of 5 to 60 hetero aryl group, and an aryl amine of the C ₆ ~ C _60,
The aryl group and heteroaryl group are each independently C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, 3 to 40 nuclear atoms Heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ Alkyl silyl group, C ₆ ~ C ₆₀ aryl silyl 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 It may be substituted with one or more selected from the group consisting of an aryl phosphine oxide group and an arylamine group of C ₆ ~ C ₆₀ , wherein when substituted with a plurality of substituents they may be the same or different from each other. Compound represented by the following formula (4):
[Formula 4]

In Chemical Formula 4,
V, W, Y and Z are the same as or different from each other, and are each independently C (R ₁ ) or N, provided that at least one of the plurality of V, W, Y and Z is N,
L is a single bond or is selected from the group consisting of a C ₆ ~ C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
R ₁ to R ₃ are the same or different and are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ 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 phosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, C ₆ ~ C ₆₀ Diaryl phosphinyl group and C ₆ ~ C ₆₀ Aryl amine group May be selected from, or adjacent R ₁ , R ₂ , or R ₃ may combine to form a ring;
a and b are each independently an integer of 0 to 4,
The arylene group and heteroarylene group of L, the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl of R ₁ to R ₃ The group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C ₆ to C ₆₀ aryl group, heteroaryl of nuclear atoms of 5 to 60 aryl group, C ₁ ~ C ₄₀ of the alkyloxy group, C ₆ ~ C ₆₀ of the aryloxy group, C ₁ ~ C ₄₀ alkylsilyl group, C ₆ ~ aryl of C ₆₀ silyl group , 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 ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ aryl of C ₆₀ Amine It may be substituted with one or more substituents selected from the group consisting of groups, wherein when there are a plurality of the substituents, they may be the same or different from each other. The method of claim 4, wherein
Compound represented by the formula (4) is a compound, characterized in that represented by any one of the following formula (5).
[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 5 to 7,
V, W, Y, Z, L, R ₂ , R ₃ and a are the same as defined in claim 4, respectively.
Rings B, C and D are the same or different and each is monocyclic or polycyclic alicyclic ring, monocyclic or polycyclic heteroalicyclic ring, monocyclic or polycyclic aromatic ring, or monocyclic or polycyclic heteroaromatic Ring,
X is selected from the group consisting of N (Ar ₃ ), O, S, and C (Ar ₄ ) (Ar ₅ );
Ar ₃ to Ar ₅ are the same or different and are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ 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 phosphanyl group, C ₆ ~ C ₆₀ Monoaryl phosphinyl group, C ₆ ~ C ₆₀ Diaryl phosphinyl group and C ₆ ~ C ₆₀ Aryl amine group Is selected from;
Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl of Ar ₃ to Ar ₅ boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group each independently hydrogen, deuterium (D), a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group , C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₆₀ Aryl group, Nuclear atoms 5 to 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 alkylboron group, aryl of C ₆ ~ C ₆₀ boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylamine It may be substituted with a substituent, wherein when the substituent is plural, they may be the same or different from each other. The method of claim 4, wherein
The rings B, C and D are each independently a monocyclic or polycyclic aromatic ring having 6 to 18 carbon atoms, or a monocyclic or polycyclic heteroaromatic ring having 5 to 18 nuclear atoms. The method according to claim 1 or 4,
N in the plurality of V, W, Y and Z is 1 to 4 compounds. The method according to claim 1 or 4,
The spyroskeleton containing at least one of V, W, Y and Z is represented by any one of the following structural formulas.

Where
* Denotes a part bonded to L of Formula 1 or Formula 4. The method according to claim 1 or 4,
The L is a single bond or a compound characterized in that the linker selected from the following structural formula.

An organic electroluminescent device comprising an anode, a cathode and at least one organic material layer interposed between the anode and the cathode, wherein at least one of the at least one organic material layer comprises the compound of claim 1. The method of claim 9,
The organic material layer comprising the compound is selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and an electron transport auxiliary layer.