KR20180022189A - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device comprising the same. The compound according to the present invention is used for an organic compound layer, preferably a light emitting layer, of an organic electroluminescent device so as to improve the luminous efficiency, the driving voltage, and the life of the organic electroluminescent device.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic compound and an organic electroluminescent device including the organic compound.

The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescence device and an organic electroluminescence device including the same.

The electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965 were followed up with the observation of organic thin film emission from Bernanose in the 1950s. In 1987, Tang The organic light emitting device having a laminated structure in which the hole layer and the functional layer of the light emitting layer are divided. Thereafter, in order to form a high efficiency and high number of organic electroluminescent devices, each organic material layer has been developed into a form in which each organic material layer has been introduced into the device, leading to the development of specialized materials used therefor.

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

The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials to realize better natural colors. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material.

The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescence, the phosphorescent dopant as well as phosphorescent host materials are being studied extensively.

Up to now, hole injecting layer, hole transporting layer. NPB, BCP and Alq ₃ are widely known as electron transporting layer materials and anthracene derivatives as light emitting layer materials. Particularly, metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like having advantages in terms of efficiency improvement of the light emitting layer material are blue, green, 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent dopant material for red phosphorescent dopants.

However, conventional organic material layers are advantageous from the viewpoint of light emitting properties, but their thermal stability is not very good due to their low glass transition temperature, and thus they are not satisfactory in terms of lifetime of the organic electroluminescent device. Therefore, development of an organic layer material having excellent performance is required.

The present invention has been made to solve the above problems and it is an object of the present invention to provide a novel compound capable of improving the efficiency, lifetime and stability of the organic electroluminescent device and an organic electroluminescent device using the compound.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1): < EMI ID =

[Chemical Formula 1]

In Formula 1,

X ₁ is selected from the group consisting of S, O, N (Ar ₁ ) and C (Ar ₂ ) (Ar ₃ );

A is a substituent represented by the following formula (2);

Ar ₁ to Ar ₃ are each independently a substituent represented by the following formula (3);

(2)

In Formula 2,

Y ₁ is selected from the group consisting of S, O, N (Ar ₄ ) and C (Ar ₅ ) (Ar ₆ );

Q ₁ and Q ₂ are each independently selected from the group consisting of C ₆ -C ₃₀ arenes and heteroaryls having 5 to 30 nucleus atoms;

m is an integer from 0 to 4;

Ar ₄ to Ar ₆ and R ₁ are each independently a substituent represented by the following formula (4), and when a plurality of R _{1 s} are present, they are the same or different;

 (3)

In Formula 3,

* Denotes the part where the bond is made;

L ₁ is selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;

R ₂ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting of C ₆₀ aryl amine, the combination group adjacent to form a condensed ring;

Arylene group and a heteroarylene group, an alkyl group of the R ₂ of the L _1, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₁ to C ₄₀ alkyl group, a C ₁ to C ₄₀ alkyl group, an aryl group, ₂ ~ C ₄₀ alkenyl group, an aryloxy group of C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of, C ₁ ~ alkyloxy of C _40, C ₆ ~ C ₆₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ a C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of the O Aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl and resilyl;

[Chemical Formula 4]

In Formula 4,

* Denotes the part where the bond is made;

L ₂ is selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;

R ₃ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting of C ₆₀ aryl amine, the combination group adjacent to form a condensed ring;

Arylene group and a heteroarylene group, an alkyl group of the R ₃ of the L _2, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₁ to C ₄₀ alkyl group, a C ₁ to C ₄₀ alkyl group, an aryl group, ₂ ~ C ₄₀ alkenyl group, an aryloxy group of C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of, C ₁ ~ alkyloxy of C _40, C ₆ ~ C ₆₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ a C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of the O A hydroxyl group, a hydroxyl group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group and a resilyl group.

The present invention provides an organic electroluminescent device including a cathode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes one or more compounds represented by Formula 1 .

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

As used herein, the term " alkenyl " is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl, But are not limited to, allyl, isopropenyl, 2-butenyl, and the like.

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

&Quot; Aryl " in the present invention means a monovalent substituent derived from a C6-C60 aromatic hydrocarbon having a single ring or a combination of two or more rings. Further, it is preferable that two or more rings are condensed with each other and only carbon atoms are contained as the ring-forming atoms (for example, the number of carbon atoms may be from 8 to 60) and the whole molecule is a non-aromacity monovalent Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein one or more carbons, preferably one to three carbons, of the ring are substituted with a heteroatom selected from N, O, P, S and Se. In addition, it is preferable that two or more rings are pendant or condensed with each other, and include hetero atoms selected from N, O, P, S and Se besides carbon as a ring-forming atom, < / RTI > aromacity). Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as, for example, phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, Click ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, " aryloxy " means a monovalent substituent represented by RO-, and R represents aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

The term " alkyloxy " in the present invention means a monovalent substituent group represented by R'O-, wherein R 'represents 1 to 40 alkyl, and may be linear, branched or cyclic . ≪ / RTI > Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

&Quot; Arylamine " in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

&Quot; Cycloalkyl " in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

&Quot; Heterocycloalkyl " in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one of the carbons, preferably one to three carbons, S or Se. ≪ / RTI > Examples of such heterocycloalkyls include, but are not limited to, morpholine, piperazine, and the like.

&Quot; Alkylsilyl " in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, and " arylsilyl " means silyl substituted with aryl having 5 to 60 carbon atoms.

In the present invention, the term "condensed rings" means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

Since the compound of the present invention is excellent in thermal stability, carrier transport ability, light emitting ability, and the like, it can be effectively applied as an organic material layer material of an organic electroluminescent device.

In addition, the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel, etc. in terms of light emitting performance, driving voltage, lifetime and efficiency.

1 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
2 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The novel compounds of the present invention can be represented by the following formula

[Chemical Formula 1]

In Formula 1,

X ₁ is selected from the group consisting of S, O, N (Ar ₁ ) and C (Ar ₂ ) (Ar ₃ );

A is a substituent represented by the following formula (2);

Ar ₁ to Ar ₃ are each independently a substituent represented by the following formula (3);

(2)

In Formula 2,

Y ₁ is selected from the group consisting of S, O, N (Ar ₄ ) and C (Ar ₅ ) (Ar ₆ );

Q ₁ and Q ₂ are each independently selected from the group consisting of C ₆ -C ₃₀ arenes and heteroaryls having 5 to 30 nucleus atoms;

m is an integer from 0 to 4;

Ar ₄ to Ar ₆ and R ₁ are each independently a substituent represented by the following formula (4), and when a plurality of R _{1 s} are present, they are the same or different;

(3)

In Formula 3,

* Denotes the part where the bond is made;

L ₁ is selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;

R ₂ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting of C ₆₀ aryl amine, the combination group adjacent to form a condensed ring;

Arylene group and a heteroarylene group, an alkyl group of the R ₂ of the L _1, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₁ to C ₄₀ alkyl group, a C ₁ to C ₄₀ alkyl group, an aryl group, ₂ ~ C ₄₀ alkenyl group, an aryloxy group of C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of, C ₁ ~ alkyloxy of C _40, C ₆ ~ C ₆₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ a C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of the O Aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl and resilyl;

[Chemical Formula 4]

In Formula 4,

* Denotes the part where the bond is made;

L ₂ is selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;

R ₃ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting of C ₆₀ aryl amine, the combination group adjacent to form a condensed ring;

Arylene group and a heteroarylene group, an alkyl group of the R ₃ of the L _2, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₁ to C ₄₀ alkyl group, a C ₁ to C ₄₀ alkyl group, an aryl group, ₂ ~ C ₄₀ alkenyl group, an aryloxy group of C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of, C ₁ ~ alkyloxy of C _40, C ₆ ~ C ₆₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ a C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of the O A hydroxyl group, a hydroxyl group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group and a resilyl group.

INDUSTRIAL APPLICABILITY The present invention provides a novel indolophlorocene compound having excellent thermal stability, carrier transporting ability and light emitting ability. Specifically, the novel organic compound according to the present invention has a structure in which a carbazole moiety is bonded to indoloflorans to form a basic skeleton, and various substituents are bonded or condensed to the basic skeleton.

In general, the phosphorescent light emitting layer among the organic material layers included in the organic electroluminescent device includes a host and a dopant to increase the color purity and increase the luminous efficiency. At this time, the host should have a triplet energy gap higher than the dopant. That is, the energy of the lowest excitation state of the host must be higher than the energy of the lowest emission state of the dopant in order to effectively provide phosphorescence from the dopant.

However, in the case of the compound represented by the above formula (1) provided in the present invention, the indolofloransene structure portion has a broad singlet energy level and a high triplet energy level. Furthermore, when a specific substituent is introduced into the structure in which the indole fluoransene carbazole is bonded, it can exhibit a higher energy level than the dopant when applied to the host of the light emitting layer.

Further, since the compound has a high triplet energy as described above, it is possible to prevent the exciton generated in the light emitting layer from diffusing (moving) to the adjacent electron transporting layer or hole transporting layer. Therefore, the compound according to the present invention can be used as an organic layer material of an organic electroluminescent device, and can preferably be used as a light emitting layer material (blue, green and / or red phosphorescent host material).

In addition, the compound of formula (1) has a structure in which various substituents, especially an aryl group and / or a heteroaryl group, are introduced into the basic skeleton, whereby the molecular weight of the compound is significantly increased and thus the glass transition temperature is improved, , CBP). ≪ / RTI > The compound is also effective for inhibiting crystallization of the organic material layer. In addition, when a heteroaryl group is introduced, it has a bipolar characteristic and exciton formation is better and the charge balance of holes and electrons is improved, so that better driving voltage and efficiency characteristics can be obtained than when an aryl group is introduced.

As described above, in the present invention, the compound represented by the formula (1) is used as an organic material layer of an organic electroluminescent device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), an electron transporting / The performance and lifetime characteristics of the organic electroluminescent device can be greatly improved when the organic electroluminescent device is applied to an injection layer material, a light emitting auxiliary layer material, and a life improving layer material. Such an organic electroluminescent device can consequently maximize the performance of a full-color organic luminescent panel.

According to one preferred embodiment of the present invention, the compound may be represented by the following general formula (5)

[Chemical Formula 5]

In Formula 5,

X ₁ and A are each as defined in the above formula (1).

In the present invention, the substituent is connected to the 12-position corresponding to the active site of the compound represented by the formula (5), whereby the physico-chemical properties of the material to which the compound is applied are stabilized, The voltage can be secured.

According to a preferred embodiment of the present invention, X ₁ may be S or O.

According to a preferred embodiment of the present invention, the compound may be represented by any one of the following formulas (6) to (12):

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

In the above formulas (6) to (12)

Each of Ar ₁ to Ar ₆ , R ₁ , m and Q ₁ to Q ₂ is as defined in the above formulas (1) and (2).

According to one preferred embodiment of the present invention, when the compound is applied to an organic electroluminescent device, the compound is represented by any one of the formulas 6 to 8, 10 and 11, and more preferably, And high current efficiency can be secured.

According to one preferred embodiment of the present invention, A may be a substituent represented by the following general formula (13) or (14):

[Chemical Formula 13]

[Chemical Formula 14]

In the above formulas 13 and 14,

* Denotes the part where the bond is made;

Y ₁ , R ₁ and m are each as defined in the above formula (2).

According to a preferred embodiment of the present invention, L ₁ and L ₂ are each independently a single bond or a linker represented by any one of the following formulas A-1 to A-7:

In the above Formulas A-1 to A-7,

* Denotes the part where the bond is made;

Y ₂ is O or S;

Z ₁ to Z ₃ are each independently N or C (R ₅ );

R ₄ and R ₅ are each independently selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, To 60 heteroaryl groups, and when a plurality of R _{5 s} are present, they are the same as or different from each other;

The alkyl, alkenyl, alkynyl, aryl and heteroaryl groups of R ₄ and R ₅ are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl , A C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, C ₆ ~ aryl of C ₆₀ amine group, a C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron in the group, aryl of C ₆ ~ C ₆₀ boron group, C ₆ ~ C ₆₀ aryl phosphazene group, one selected from the group consisting arylsilyl of C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of the And when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, at least one of L ₁ and L ₂ may be a linker represented by any of formulas A-5 to A-7, wherein at least one of Z ₁ and Z ₂ is N When applied to an organic electroluminescent device, a low driving voltage and high current efficiency can be secured.

According to a preferred embodiment of the present invention, R ₄ may be selected from the group consisting of a phenyl group, a biphenyl group and a naphthalenyl group.

According to a preferred embodiment of the present invention, each of R ₂ and R ₃ may independently be a substituent represented by any one of the following formulas B-1 to B-4:

In the above B-1 to B-4,

* Denotes the part where the bond is made;

Z ₄ to Z ₈ are each independently N or C (R ₆ );

Y ₃ is selected from the group consisting of S, O, N (Ar ₇ ) and C (Ar ₈ ) (Ar ₉ );

R ₆ and Ar ₇ to Ar ₉ are each independently hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, and a nucleus A heteroaryl group having 5 to 60 atoms, and when R ₆ is plural, they are the same or different;

The alkyl, alkenyl, alkynyl, aryl and heteroaryl groups of R ₆ and Ar ₇ to Ar ₉ are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl An arylamine group of C ₆ to C ₆₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl boron group, C ₆ ~ aryl of C ₆₀ boron group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ from the group consisting arylsilyl of C ₆₀ of And when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, at least one of R ₂ and R ₃ may be a substituent represented by the above formula (B-1), wherein at least one of Z ₄ to Z ₇ is N, A low driving voltage and a high current efficiency can be secured when applied to a light emitting device.

According to a preferred embodiment of the present invention, each of R ₂ and R ₃ may independently be a substituent represented by any one of the following formulas C-1 to C-10:

In the above formulas C-1 to C-10,

* Denotes the part where the bond is made;

t is an integer from 0 to 5,

u is an integer from 0 to 4;

v is an integer from 0 to 3;

w is an integer from 0 to 2;

R ₇ is heavy hydrogen, 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 ₆ ~ C ₆₀ aryl group, the nucleus of atoms of A C ₆ to C ₆₀ alkyloxy group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryloxy group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ heteroaryl group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, _A C ₆ to C ₆₀ arylamine group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphonyl group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or of, by combining groups of adjacent, may form a fused ring, wherein R ₇ in this case multiple individual which Are the same or different from each other;

Alkyl group of the R _7, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, _A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ the arylboronic group, one member selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group in the silyl If substituted with a substituent or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, at least one of R ₂ and R ₃ may be a substituent represented by any one of the above formulas C-5 to C-10, more preferably a compound represented by the formula C-7 or C -10, and when it is applied to an organic electroluminescent device, a low driving voltage and a high current efficiency can be ensured.

According to a preferred embodiment of the present invention, R ₇ may be selected from the group consisting of a phenyl group, a biphenyl group, a naphthalenyl group, a dibenzofuranyl group and a dibenzothiophenyl group.

According to a preferred embodiment of the present invention, the compound represented by Formula 1 is the compound represented by Formula 10, wherein R ₃ is a substituent represented by any one of Formulas C-5 to C-10. When applied to an organic electroluminescent device, a low driving voltage and a high current efficiency can be secured.

According to a preferred embodiment of the present invention, the compound represented by Formula 1 is a compound represented by any one of Formulas 6 to 8, and at least one of L ₁ and L ₂ , more preferably L _1, May be a linker represented by any one of A-5 to A-7, wherein at least one of Z ₁ and Z ₂ is N. When applied to an organic electroluminescent device, a low driving voltage and a high current efficiency can be secured have.

According to a preferred embodiment of the present invention, the compound represented by Formula 1 is a compound represented by any one of Formulas 6 to 8, A is a substituent represented by Formula 14, and L ₁ and L ₂ At least one, more preferably L ₁ may be a linker represented by any one of formulas A-5 to A-7, wherein at least one of Z ₁ and Z ₂ is N, which is applied to an organic electroluminescent device A low driving voltage and a high current efficiency can be secured.

According to a preferred embodiment of the present invention, the compound represented by Formula 1 is the compound represented by Formula 10 or Formula 11, and at least one of L ₁ and L ₂ , more preferably L ₁ , 5 to A-7, wherein at least one of Z ₁ and Z ₂ is N. When this compound is applied to an organic electroluminescent device, a low driving voltage and a high current efficiency can be secured.

The compounds represented by formula (1) of the present invention can be represented by the following compounds, but are not limited thereto:

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

2. Organic Field  Light emitting element

Another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the general formula (1) according to the present invention described above.

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes Include compounds represented by the above formula (1). At this time, the compounds may be used singly or in combination of two or more.

The at least one organic material layer may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, a light emitting auxiliary layer, a life improving layer, an electron transporting layer, an electron transporting auxiliary layer and an electron injecting layer, 1 < / RTI >

The structure of the organic electroluminescent device according to the present invention is not particularly limited. For example, referring to FIG. 1, an anode 10 and a cathode 20 facing each other, 20). ≪ / RTI > Here, the organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34. A hole transporting auxiliary layer 33 may be interposed between the hole transporting layer 31 and the light emitting layer 32. An electron transporting auxiliary layer 35 may be interposed between the electron transporting layer 34 and the light emitting layer 32 can do.

2, the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, and the electron transport layer 34 and the cathode And an electron injection layer (36) may be further included between the first electrode (20) and the second electrode (20).

In the present invention, the hole injection layer 37 deposited between the hole transport layer 31 and the anode 10 improves the interfacial properties between the ITO used as the anode and the organic material used as the hole transport layer 31 But the surface of the ITO layer is applied to the upper surface of the ITO which is not planarized to soften the surface of the ITO. The layer can be used without any particular limitation as long as it is commonly used in the art. For example, an amine compound can be used But is not limited thereto.

The electron injection layer 36 is a layer which is stacked on the electron transport layer 34 to facilitate injection of electrons from the cathode to ultimately improve power efficiency and is commonly used in the art . For example, materials such as LiF, Liq, NaCl, CsF, Li ₂ O, and BaO can be used.

In addition, although not shown in the drawings, the light emitting layer 32 may further include a light emitting auxiliary layer between the hole transporting auxiliary layer 33 and the light emitting layer 32. The light-emission-assisting layer may serve to adjust the thickness of the organic layer 30 while serving to transport holes to the light-emitting layer 32. The light-emission-assisting layer may include a hole-transporting material and may be made of the same material as the hole-transporting layer 31.

In addition, although not shown in the drawings, a life improving layer may be further included between the electron transporting auxiliary layer 35 and the light emitting layer 32. Holes moving in the organic light emitting device due to the ionization potential level in the light emitting layer 32 are blocked by the high energy barrier of the lifetime enhancing layer and do not diffuse or move to the electron transporting layer and consequently function to limit the holes to the light emitting layer . The function of restricting the holes to the light emitting layer prevents diffusion of holes to the electron transporting layer that transports electrons by reduction, thereby suppressing the lifetime degradation due to the irreversible decomposition reaction by oxidation and contributing to improvement in the lifetime of the organic light emitting device .

In the present invention, the indole fluoransene structure portion of the compound represented by Formula 1 has a broad singlet energy level and a high triplet energy level. Furthermore, when a specific substituent is introduced into the structure in which the indole fluoransene carbazole is bonded, it can exhibit a higher energy level than the dopant when applied to the host of the light emitting layer.

Further, since the compound has a high triplet energy as described above, it is possible to prevent the exciton generated in the light emitting layer from diffusing (moving) to the adjacent electron transporting layer or hole transporting layer. Therefore, the compound according to the present invention can be used as an organic material layer material of an organic electroluminescent device, and is preferably used as a material for a light emitting layer, thereby greatly improving the luminous efficiency, brightness, power efficiency, thermal stability and lifetime of the organic electroluminescent device. .

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

In addition, the organic electroluminescent device according to the present invention may further include an insulating layer or an adhesive layer at the interface between the electrode and the organic layer as well as the anode, one or more organic layers and the cathode sequentially laminated as described above.

The organic electroluminescent device of the present invention includes materials and methods known in the art, except that at least one or more of the organic material layers (for example, the electron transporting auxiliary layer) is formed to include the compound represented by Formula 1 To form another organic material layer and an electrode.

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

The substrate usable in the present invention is not particularly limited, and a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.

The anode material may be made of a conductor having a high work function to facilitate injection of holes, for example, metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.

The negative electrode material may be made of a conductor having a low work function so as to facilitate electron injection and may be made of a material having a low work function such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, The same metal or an alloy thereof; And multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.

[ Preparation Example  One] Of Core1  synthesis

< Step 1 > 2- ( Fluoranthene Yl) -4,4,5,5- Tetramethyl -1,3,2- Dioxaborolan  synthesis

3-bromofluoranthene (30 g, 106.7 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'- (32.5 g, 128 mmol), Pd (dppf) Cl ₂ (2.61 g, 3.2 mmol), KOAc (31.4 g, 320 mmol) and 1,4- dioxane And the mixture was stirred at 110 DEG C for 12 hours.

After completion of the reaction, the residue was purified by column chromatography to obtain 25 g of 2- (fluoranthene-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane %).

<Step 3> 3 - (5- Chloro -2- Nitrophenyl ) Fluoranthene  synthesis

Dioxaborolane (25 g, 76.16 mmol), 4-chloro- 2 (fluoranthene-3-yl) -4,4,5,5-tetramethyl- -iodine-1-nitrobenzene (21.6 g, 76.16 mmol), Pd (PPh 3) 4 (2.64 g, 3 mol%), K 2 CO 3 (31.6 g, 228 mmol) in a 300 ml / 100 ml 1, 4-dioxane / H ₂ O was added, and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 3- (5-chloro-2-nitrophenyl) fluoranthene (20 g, yield 73%) was obtained by column chromatography.

<Step 4> 12- Chloro -9H- Fluoreno [9,1-bc] carbazole  synthesis

B, e] [1,4] dioxine (20 g, 55.89 mmol) and triphenylphosphine (36.6 g, 139.7 mmol) were dissolved in a mixture of 1,4-bis Dichlorobenzene, and the mixture was stirred for 12 hours at 150 ° C. After completion of the reaction, the mixture was extracted with methylene chloride, and the mixture was filtered through a plug of MgSO ₄ , and the solvent was removed from the filtered organic layer. -9H-fluoreno [9,1-bc] carbazole (12 g, yield 66%).

<Step 5> The 12- Chloro -9-phenyl-9H- Fluoreno [9,1-bc] carbazole  synthesis

(12 g, 36.83 mmol), iodobenzene (9 g, 44.2 mmol), Cu powder (0.23 g, 3.68 mmol), K ₂ CO ₃ (10.2 g, 73.66 mmol) and 100 ml of nitrobenzene were mixed and stirred at 250 ° C for 6 hours.

After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO ₄ . After removing the solvent from the organic layer from which water had been removed, the residue was purified by column chromatography to obtain 12-chloro-9-phenyl-9H-fluoreno [9,1- bc] carbazole (12 g, yield 81%).

<Step 6> Of Core1  synthesis

 Instead of 2- (fluoranthene-3-yl) -4,4,5,5-tetramethyl-1,3,2-dioxabororane, 3- (4,4,5,5-tetramethyl- -9H-carbazole (10.5 g, 35.83 mmol) was used instead of 4-chloro-2-iodo-1-nitrobenzene, (10 g, yield 63%) was obtained by following the same procedure as in <Step 3> except that 9-fluoro [9,1-bc] carbazole (12 g, 29.85 mmol) was used.

^{1 H-NMR: δ 7.18 (} t, 1H), 7.75 (m, 15H), 8.12 (m, 4H), 8.30 (d, 1H), 8.45 (m, 2H) 12.10 (s, 1H)

[ Preparation Example  2] Core2  synthesis

The same procedure as in [Step 5] of [Preparation Example 1] was performed except that 3-bromo-1,1'-biphenyl (8.5 g, 36.83 mmol) was used instead of iodobenzene, 9-fluoro [9,1-bc] carbazole instead of 9-phenyl-9H-fluoreno [9,1- ] Carbazole (11 g, 23 mmol) was used in place of tert-butyllithium in Example 1 to obtain Core 2 (9.5 g, yield 68%).

¹ H-NMR :? 7.15 (t, IH), 7.72 (m, 2H), 8.19 (m, 4H), 8.46

[ Preparation Example  3] Core3  synthesis

Fluoro [9,1-bc] carbazole (10 g, 30.69 mmol) was used instead of 12-chloro-9-phenyl-9H-fluoreno [9,1- - (4,4,5,5-tetramethyl-1,3,2-dioxabororane-2-yl) -9H- Step 6> of [Preparation Example 1] was repeated except that tetramethyl-1,3,2-dioxabororen-2-yl) -9H-carbazole (13.6 g, 36.83 mmol) The same procedure was carried out to obtain Core 3 (10.8 g, yield 66%).

¹ H-NMR: 8 7.20 (m, 2H), 7.82 (m, 15H), 8.20 (m, 4H), 8.33 (d,

[ Preparation Example  4] Core4  synthesis

9 - ([l, l ' - bis &lt; RTI ID = 0.0 &gt; (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (16.4 g, 36.83 mmol) , Core 4 (11.5 g, yield 62%) was obtained in the same manner as in [Preparation Example 3] above.

¹ H-NMR :? 7.16 (t, 1H), 7.68 (m, 18H), 8.17 (m, 5H), 8.32 (d,

[ Preparation Example  5] Core5  Synthesis of

Dibenzo [b, d] azepine instead of 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxabororane- 2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (10.8 g, 36.83 mmol) was used in place of [ The same procedure was followed to obtain Core 5 (10.2 g, yield 73%).

^{1 H-NMR: δ 7.38 (} m, 2H), 7.55 (m, 2H), 7.95 (m, 10H), 8.12 (m, 2H), 8.42 (m, 2H) 12.10 (s, 1H)

[ Preparation Example  6] Core6  synthesis

Dibenzo [b, d] azepine instead of 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxabororane- Preparation Example 3] was repeated except that 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (11.4 g, 36.83 mmol) was used instead of [ To obtain Core6 (9.8 g, yield 67%).

^{1 H-NMR: δ 7.54 (} m, 3H), 7.76 (m, 3H), 7.95 (m, 5H), 8.14 (m, 4H), 8.45 (m, 3H) 12.05 (s, 1H)

[ Preparation Example  7] Core7  Synthesis of

(4,4,5,5-tetramethyl-1,3,2-dioxabororen-2-yl) -9H-carbazole was used instead of 9- [Preparative Example 3] and (4) were repeated except that the above-prepared [(3-methyl-2-oxo-benzo [c] The same procedure was carried out to obtain Core 7 (11.2 g, yield 63%).

¹ H-NMR :? 7.60 (m, 18H), 8.13 (m, 3H), 8.34 (d,

[ Preparation Example  8] Core8  Synthesis of

<Step 1> Synthesis of 3- (5- Bromo -2- Fluorophenyl )-2- Of ethoxyfluoranthene  synthesis

Bromo-1-fluoro-2-iodobenzene (30 g, 99.7 mmol) and Pd (PPh 3) were added to a solution of (2-ethoxyfluoranthene-3-yl) boronic acid (34.71 g, 119.64 mmol) ₃ ) ₄ (3.45 g, 3 mol%), K ₂ CO ₃ (41.33 g, 299.1 mmol) and 400 ml / 100 ml / 100 ml of toluene / EtOH / H ₂ O were added and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 3- (5-bromo-2-fluorophenyl) -2-ethoxyfluoranthene (23.5 g, yield 56%) was obtained by column chromatography.

&Lt; Step 2 > 3- (5- Bromo -2- Fluorophenyl ) Fluoranthene 2-ol

In a nitrogen atmosphere 4- (5-Bromo-2-fluoro-phenyl) -2-ethoxy fluoranthene (23.5 g, 56.04 mmol) was dissolved in 300ml of CH ₂ Cl ₂ boron tree in 100ml CH ₂ Cl ₂ bromide (16.84 g, 67.25 mmol) were mixed and stirred at 0 ° C for 18 hours. After completion of the reaction, water was added and stirred. NaHCO ₃ was added and extracted with ethyl acetate. The organic layer was dried over MgSO ₄ and filtered under reduced pressure. The filtrated organic layer was distilled under reduced pressure, and then 3- (5-bromo-2-fluorophenyl) fluoranthene-2-ol (20 g, yield 91%) was obtained by column chromatography.

<Step 3> 12- Bromofluorantano [2,3-b] benzofuran  synthesis

(20 g, 51.12 mmol), NMP (200 mL) and K ₂ CO ₃ (14.1 g, 102.23 mmol) were added, and then 200 C &lt; / RTI &gt; for 2 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, 12-bromofluorantano [2,3-b] benzofuran (12.4 g, yield 65%) was obtained by column chromatography.

<Step 4> Core8  synthesis

Except that 12-bromofluorantano [2,3-b] benzofuran (12.4 g, 33.4 mmol) was used instead of 4-bromo-1-fluoro-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (11.75 g, 40.08 mmol) instead of 3- The same procedure as in [Step 1] of [Preparation Example 8] was carried out to obtain Core 8 (11.5 g, yield 75%).

^{1 H-NMR: δ 7.15 (} t, 1H), 7.68 (m, 12H), 8.12 (m, 3H), 8.40 (m, 2H), 12.08 (s, 1H)

[ Preparation Example  9] Core9  Synthesis of

<Step 1> 5 - Chloro -2-( Fluoranthene -2- Ithio ) Synthesis of aniline

2-Bromofluoranthene (20 g, 71.13 mmol), 2-amino-4-chlorobenzenethiol (13.62 g, 85.36 mmol) and K ₂ CO ₃ 19.6 g (142.27 mmol) And the mixture was refluxed and stirred. After completion of the reaction, the reaction mixture was extracted with dichloromethane. The organic layer was dried over MgSO ₄ and filtered under reduced pressure. The filtrated organic layer was distilled under reduced pressure, and then the target compound, 5-chloro-2- (fluoranthene-2-ylthio) aniline (24.7 g, yield 76%) was obtained by column chromatography.

<Step 2> 12- Chlorobenzo [b] fluorantheno [3,2-d] thiophene  synthesis

2- (5-bromo-naphthalene-1-ylthio) aniline (24.7 g, 68.63 mmol), HCl 20ml, ethyl _{200ml, NaNO 2 (47.35g, 686.35} mmol) and H ₂ O aqueous solution 70ml to 60ml H ₂ O mixture Was added dropwise at 0? 5 占 폚 for about 1 hour and stirred for 12 hours. A solution of CuSO ₄ (49.3 g, 308.8 mmol) in 800 ml of H ₂ O and 50 ml of HCl was added and the mixture was refluxed with stirring for 1 hour. The temperature was lowered and the solid was filtered to obtain 12-chlorobenzo [b] fluorantheno [3,2-d] thiophene (22.3 g, yield: 95%).

<Step 3> Core9's  synthesis

(24.7 g, 72.04 mmol) was used instead of 12-chloro-9-phenyl-9H-fluoreno [9,1- , Core9 (25.2 g, yield 74%) was obtained in the same manner as in [Step 6] of [Preparation Example 1].

^{1 H-NMR: δ 7.22 (} t, 1H), 7.65 (m, 6H), 8.03 (d, 1H), 8.19 (m, 5H), 8.43 (m, 2H), 12.15 (s, 1H)

[ Synthetic example  One] Inv 2 of  synthesis

Pd (t-Bu) ₃ (0.25 g, 0.28 mmol) and Pd ₂ (dba) ₃ (5.0 g, 9.38 mmol) (0.38 g, 0.94 mmol) and sodium tert-butoxide (1.80 g, 18.7 mmol) were added to 80 ml of toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO ₄ . After removing the solvent of the filtered organic layer, Inv 2 (4.8 g, yield 75%) was obtained by column chromatography.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 684

[ Synthetic example  2] In 17  synthesis

(5.0 g, 9.38 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.0 g, 11.26 mmol), NaH (0.045 g, 1.87 mmol) and DMF 100 ml) were mixed and stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was poured into water and the solid compound was filtered, and then purified by column chromatography (Hexane: MC = 2: 1 (v / v)) to obtain Inv 17 (5.1 g, yield 71%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 763

[ Synthetic example  3] Inv  Synthesis of 22

Except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (3.87 g, 11.26 mmol) was used instead of 3-bromo-1,1'- Was subjected to the same procedure as in Synthesis Example 1 to obtain Inv 22 (5.7 g, yield 72%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 839

[ Synthetic example  4] Inv 29 of  synthesis

Dibenzo [b, d] furan-3-yl) -6-phenyl-butyramide instead of 2- (3- chlorophenyl) The same procedure as in Synthesis Example 2 was carried out except that 1,3,5-triazine (4.0 g, 11.26 mmol) was used to obtain Inv 29 (5.0 g, yield 62%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 853

[ Synthetic example  5] Inv 33 of  synthesis

The procedure of Synthesis Example 1 was repeated except that 2-chloro-4-phenylquinazoline (2.71 g, 11.26 mmol) was used instead of 3-bromo-1,1'- g, yield: 62%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 736

[ Synthetic example  6] Inv 39 of  synthesis

The procedure of Synthesis Example 1 was repeated except that 3-chloro-1-phenylbenzo [f] quinazoline (3.27 g, 11.26 mmol) was used instead of 3-bromo-1,1'- 39 (4.2 g, yield 57%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 786

[ Synthetic example  7] Inv 92 of  synthesis

Except that Core 3 (5.0 g, 93.87 mmol) was used in the place of Core 1 and 2-bromodibenzo [b, d] furan (2.78 g, 11.26 mmol) was used instead of 3-bromo- Was subjected to the same procedure as in Synthesis Example 1 to give Inv 92 (4.8 g, yield 73%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 698

[ Synthetic example  8] Inv 98  synthesis

Except that Core2 (5.0 g, 93.87 mmol) was used instead of Core 1 and 2-chloro-4,6-diphenyl-1,3,5- The same procedure as in Synthesis Example 2 was carried out except that triazine (4.73 g, 11.26 mmol) was used to obtain Inv 98 (5.5 g, yield 64%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 915

[ Synthetic example  9] Inv 103  synthesis

4-yl) -4- (3-chlorophenyl) -6-phenyl-1,3,5-tri The same procedure as in Synthesis Example 7 was carried out except that azine (4.73 g, 11.26 mmol) was used to obtain Inv 103 (5.9 g, yield 69%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 915

[ Synthetic example  10] Inv 111  synthesis

B, d] furan-2-yl) -4,6-diphenyl-1,3,5-triazine (5.38 g, , 11.26 mmol), the same procedure as in Synthesis Example 7 was carried out to obtain Inv 103 (6.2 g, yield 71%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 929

[ Synthetic example  11] Inv  Synthesis of 114

Except that 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (3.56 g, 11.26 mmol) was used instead of 2-bromodibenzo [b, The same procedure as in Example 7 was followed to obtain Inv 114 (4.7 g, yield 62%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 812

[ Synthetic example  12] Inv 117's  synthesis

The same procedure as in Synthesis Example 7 was carried out except that 2-chloro-4-phenylbenzo [h] quinazoline iodobenzene (3.27 g, 11.26 mmol) was used instead of 2-bromodibenzo [b, Inv 117 (4.3 g, yield 58%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 786

[ Synthetic example  13] Inv 122  synthesis

The same procedure as in Synthesis Example 1 was carried out except that Core 4 (5 g, 82.14 mmol) was used instead of Core 1 to obtain Inv 122 (4.9 g, yield 78%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 760

[ Synthetic example  14] Inv 141 of  synthesis

 Except using 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (3.38 g, 9.85 mmol) instead of 3-bromo-1,1'- The procedure of Synthesis Example 13 was followed to obtain Inv 141 (5.3 g, yield 70%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 915

[ Synthetic example  15] Inv 147's  synthesis

Instead of 2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-tri The same procedure as in Synthesis Example 13 was carried out except that azine (4.13 g, 98.56 mmol) was used to obtain Inv 147 (5.8 g, yield 71%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 992

[ Synthetic example  16] Inv 153's  synthesis

The same procedure as in Synthesis Example 13 was carried out except that 2-chloro-4-phenylquinazoline (2.37 g, 98.56 mmol) was used instead of 3-bromo-1,1'- , Yield: 63%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 812

[ Synthetic example  17] Inv 164 of  synthesis

Except that Core5 (5.0 g, 10.92 mmol) was used in place of Core 1 and 5'-bromo-1,1 ': 3', 1 "-terphenyl (4.05 g, 13.11 mmol), the same procedure as in Synthesis Example 1 was carried out to obtain Inv 164 (5.7 g, yield 76%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 685

[ Synthetic example  18] Inv 179  synthesis

(5.0 g, 10.92 mmol) instead of Core 1 and 2-chloro-4,6-di (naphthalen-2-yl) The same procedure as in Synthesis Example 2 was carried out except that 1,3,5-triazine (4.82 g, 13.11 mmol) was used to obtain Inv 179 (5.5 g, yield 64%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 788

[ Synthetic example  19] Inv 182  synthesis

(4.5 g, 13.11 mmol) instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine in place of 5'-bromo- mmol) was used to obtain Inv 164 (6.0 g, yield 72%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 764

[ Synthetic example  20] Inv 188  synthesis

Instead of 2- (4'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl -1,3,5-triazine (5.5 g, 13.11 mmol) was used in the same manner as in Synthesis Example 17 to obtain Inv 188 (6.2 g, yield 67%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 840

[ Synthetic example  21] Inv  Synthesis of 193

The same procedure as in Preparation Example 17 was repeated, except that 2-chloro-4-phenylquinazoline (3.15 g, 13.11 mmol) was used instead of 5'-bromo-1,1 ': 3' To obtain Inv 193 (4.2 g, yield 58%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 661

[ Synthetic example  22] Inv 208  synthesis

Except that Core 6 (5.0 g, 10.55 mmol) was used in place of Core 1 and 2-bromotriphenylene (3.89 g, 12.66 mmol) was used instead of 3-bromo-1,1'- (Inv. 208, 5.5 g, yield 74%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 699

[ Synthetic example  23] Inv 217  synthesis

The procedure of Synthesis Example 2 was repeated except that Core 6 (5.0 g, 10.55 mmol) was used instead of Core 1 to obtain Inv 217 (4.5 g, yield 60%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 704

[ Synthetic example  24] Inv 225  synthesis

Except that 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (4.0 g, 12.66 mmol) was used in place of 2-bromotriphenylene Was carried out to obtain Inv225 (5.8 g, yield 70%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 779

[ Synthetic example  25] Inv 234  synthesis

The same procedure as in Synthesis Example 22 was carried out except that 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.3 g, 12.66 mmol) was used instead of 2-bromotriphenylene to obtain Inv234 5.5 g, yield 69%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 753

[ Synthetic example  26] Inv 257  synthesis

Inv 257 (4.5 g, yield 64%) was obtained by following the same procedure as in Synthesis Example 2, except that Core 7 (5.0 g, 8.58 mmol) was used instead of Core 1.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 813

[ Synthetic example  27] Inv 270  synthesis

Dibenzo [b, d] furan-2-yl) -6-phenyl-1,3,5-triazine instead of 2-chloro-4,6- (3.68 g, yield 59%) was obtained by carrying out the same procedure as in Synthesis Example 26 except that triazine (3.68 g, 10.29 mmol) was used.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 904

[ Synthetic example  28] Inv273  synthesis

The procedure of Synthesis Example 5 was repeated except that Core 7 (5.0 g, 8.58 mmol) was used instead of Core 1 to obtain Inv 273 (4.1 g, yield 61%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 786

[ Synthetic example  29] Inv275's  synthesis

The same procedure as in Synthesis Example 28 was repeated, except that 2-chloro-4- (4- (naphthalen-2-yl) phenyl) quinazoline (3.7 g, 102.97 mmol) was used instead of 2-chloro-4-phenylquinazoline To obtain Inv275 (4.5 g, yield 57%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 913

[ Synthetic example  30] Inv279  synthesis

The same procedure as in Synthesis Example 28 was carried out except that 3-chloro-1-phenylbenzo [f] quinazoline (3.0 g, 290.75 mmol) was used instead of 2-chloro-4-phenylquinazoline to obtain Inv275 , Yield: 56%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 837

[ Synthetic example  31] Inv 284  synthesis

The procedure of Synthesis Example 17 was repeated except that Core 8 (5.0 g, 10.92 mmol) was used instead of Core 5 to obtain Inv284 (5.5 g, yield 73%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 685

[ Synthetic example  32] Inv 292  synthesis

Except that 2-bromodibenzo [b, d] furan (3.24 g, 13.11 mmol) was used in place of 5'-bromo-1,1 ': 3', 1 " The same procedure was followed to obtain the desired compound Inv 292 (5.1 g, yield 75%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 623

[ Synthetic example  33] Inv298  Synthesis of

Inv298 (6.0 g, yield 65%) was obtained by following the same procedure as in Synthesis Example 8, except that Core8 (5.5 g, 13.11 mmol) was used instead of Core2.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 840

[ Synthetic example  34] Inv302  Synthesis of

(4.5 g, 13.11 mmol) instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine in place of 5'-bromo- mmol), the procedure of Synthesis Example 31 was followed to obtain Inv302 (5.8 g, yield 69%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 764

[ Synthetic example  35] Inv311  Synthesis of

(6.2 g, 13.11 mmol) instead of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine instead of 5'-bromo- mmol), the same procedure as in Synthesis Example 31 was carried out to obtain Inv 311 (6.6 g, yield 71%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 854

[ Synthetic example  36] Inv316  Synthesis of

Chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.8 g, 13.11 mmol) instead of 5'-bromo-1,1 ': 3', 1 " The procedure of Synthesis Example 31 was repeated to obtain Inv 311 (5.5 g, yield 64%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 787

[ Synthetic example  37] Inv318  Synthesis of

([1,1'-biphenyl] -4-yl) -2-chlorobenzo [h] quinazoline instead of 4'- g, 13.11 mmol) was used in place of acetic anhydride, to obtain Inv 318 (5.2 g, yield 60%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 787

[ Synthetic example  38] Inv323  Synthesis of

Except that Core 9 (5.0 g, 10.55 mmol) was used instead of Core 1 and 4-bromo-1,1'-biphenyl (2.95 g, 12.66 mmol) was used instead of 3-bromo-1,1'- The procedure of Synthesis Example 1 was repeated to obtain Inv323 (5.0 g, yield 76%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 625

[ Synthetic example  39] Inv334  Synthesis of

The same procedure as in Synthesis Example 38 was carried out except that 2-bromo-9-phenyl-9H-carbazole (4.0 g, 12.66 mmol) was used instead of 4-bromo-1,1'- (5.4 g, yield 72%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 714

[ Synthetic example  40] Inv340  Synthesis of

Except that Core 9 (5.0 g, 10.55 mmol) was used instead of Core 1 and 2-chloro-4,6-di (naphthalen-1-yl) The procedure of Synthesis Example 2 was repeated except that 1,3,5-triazine (4.66 g, 12.66 mmol) was used to obtain the desired compound Inv340 (5.1 g, yield 60%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 804

[ Synthetic example  41] Inv344  Synthesis of

([1,1'-biphenyl] -3-yl) -6- (3-chlorophenyl) -1,3,5-tri (6.6 g, yield 67) was obtained by carrying out the same procedure as in Synthesis Example 38, except that azine (6.2 g, 12.66 mmol) was used.

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 933

[ Synthetic example  42] Inv346  Synthesis of

(5.3 g, 12.66 mmol) instead of 4-bromo-1,1'-biphenyl. mmol), the procedure of Synthesis Example 38 was repeated to obtain Inv346 (6.1 g, yield 67%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 856

[ Synthetic example  43] Inv355  Synthesis of

(4.6 g, 12.66 mmol) was used instead of 2-chloro-4- (4- (naphthalen-2-yl) phenyl) quinazoline in place of 4-bromo-1,1'- Was performed to obtain Inv355 (5.2 g, yield 61%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 803

[ Synthetic example  44] Inv360  Synthesis of

Except that 1 - ([1,1'-biphenyl] -4-yl) -3-chlorobenzo [f] quinazoline (4.64 g, 12.66 mmol) was used instead of 4-bromo- The procedure of Synthesis Example 38 was repeated to obtain Inv360 (4.8 g, yield 57%).

Mass: [(M + H) &lt; ⁺ & gt ^; ]: 803

[ Example  1 ~ 28] Green organic Field  Fabrication of light emitting device

The compounds Inv2 to Inv346 synthesized in Synthesis Examples 1 to 42 were subjected to high purity sublimation purification by a conventionally known method, and a green organic electroluminescent device was fabricated according to the following procedure.

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

Thus prepared ITO transparent electrode on the m-MTDATA (60 nm) / TCTA (80 nm) / each of the compounds of Inv2 ~ Inv346 + 10% Ir ( ppy) 3 (30nm) / BCP (10 nm) / Alq 3 (30 nm ) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

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

[ Comparative Example  1] Green organic Field  Fabrication of light emitting device

A green organic electroluminescent device was fabricated in the same manner as in Example 1, except that CBP was used instead of the compound Inv2 as a luminescent host material in forming the light emitting layer.

[ Evaluation example  One]

Current efficiency and emission peak at current density (10) mA / cm &lt; 2 &gt; were measured for each of the green organic electroluminescent devices manufactured in Examples 1 to 28 and Comparative Example 1, Respectively.

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 Inv2 6.64 516 42.2 Example 2 Inv17 6.35 517 47.4 Example 3 Inv22 6.42 518 49.2 Example 4 Inv29 6.53 516 45.8 Example 5 Inv92 6.66 517 41.1 Example 6 Inv98 6.48 516 45.6 Example 7 Inv103 6.32 516 47.5 Example 8 Inv111 6.28 516 46.4 Example 9 Inv122 6.76 517 43.1 Example 10 Inv141 6.39 516 47.4 Example 11 Inv147 6.45 516 46.6 Example 12 Inv164 6.81 518 42.4 Example 13 Inv179 6.38 516 47.6 Example 14 Inv182 6.54 518 46.1 Example 15 Inv188 6.37 517 45.4 Example 16 Inv208 6.72 517 43.7 Example 17 Inv217 6.55 516 44.8 Example 18 Inv225 6.36 518 46.5 Example 19 Inv284 6.68 516 42.1 Example 20 Inv292 6.72 516 43.6 Example 21 Inv298 6.26 517 49.9 Example 22 Inv302 6.18 518 47.4 Example 23 Inv311 6.26 516 49.2 Example 24 Inv323 6.72 517 43.6 Example 25 Inv334 6.62 517 42.4 Example 26 Inv340 6.37 518 48.3 Example 27 Inv344 6.29 516 47.4 Example 28 Inv346 6.34 516 46.3 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, when the compounds Inv2 to Inv346 according to the present invention were used as a light emitting layer of a green organic electroluminescent device (Examples 1 to 28), a green organic electroluminescent device (Comparative Example 1) using conventional CBP In comparison, it can be seen that performance is better in terms of efficiency and driving voltage. Further, when the heteroaryl group containing N is substituted, it can be seen that characteristics of lower drive voltage and higher current efficiency can be secured.

[ Example  29 ~ 44] Red organic Field  Manufacturing of light emitting device

The compound synthesized in Synthesis Examples 15 to 44 was subjected to high purity sublimation purification by a conventionally known method, and then a red organic electroluminescent device was fabricated according to the following procedure.

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

Thus prepared ITO transparent electrode on the m-MTDATA (60 nm) / TCTA (80 nm) / Inv33 ~ Inv360 compound + 10% (piq) of _{2 Ir (acac) (300nm)} / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

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

A red organic electroluminescent device was fabricated in the same manner as in Example 29, except that CBP was used in place of the compound of Synthesis Example 5 as a luminescent host material in forming the light emitting layer.

The structures of m-MTDATA, (piq) ₂ Ir (acac), CBP and BCP used in Examples 29 to 44 and Comparative Example 2 are as follows.

[ Evaluation example  2]

The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 29 to 44 and Comparative Example 2. The results are shown in Table 2 below.

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 29 Inv33 4.92 12.6 Example 30 Inv39 4.84 13.6 Example 31 Inv114 4.28 14.8 Example 32 Inv117 4.14 15.8 Example 33 Inv153 4.32 14.7 Example 34 Inv193 4.25 14.6 Example 35 Inv234 4.28 15.8 Example 36 Inv257 4.34 15.6 Example 37 Inv270 4.25 13.6 Example 38 Inv273 4.32 12.8 Example 39 Inv275 4.14 15.8 Example 40 Inv279 4.32 14.7 Example 41 Inv316 4.25 14.6 Example 42 Inv318 4.28 15.8 Example 43 Inv355 4.34 15.6 Example 44 Inv360 4.25 13.6 Comparative Example 2 CBP 5.25 8.2

As shown in Table 2, when the compound according to the present invention was used as a material for a light emitting layer of a red organic electroluminescent device (Examples 29 to 44), a red organic electroluminescent device using conventional CBP as a material for a light emitting layer (Comparative Example 2 ), It can be seen that it shows excellent performance in terms of efficiency and driving voltage.

10: anode 20: cathode
30: organic layer 31: hole transport layer
32: light emitting layer 33: hole transporting auxiliary layer
34: Electron transport layer 35: Electron transport layer
36: electron injection layer 37: hole injection layer

Claims (14)

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

In Formula 1,
X ₁ is selected from the group consisting of S, O, N (Ar ₁ ) and C (Ar ₂ ) (Ar ₃ );
A is a substituent represented by the following formula (2);
Ar ₁ to Ar ₃ are each independently a substituent represented by the following formula (3);
(2)

In Formula 2,
Y ₁ is selected from the group consisting of S, O, N (Ar ₄ ) and C (Ar ₅ ) (Ar ₆ );
Q ₁ and Q ₂ are each independently selected from the group consisting of C ₆ -C ₃₀ arenes and heteroaryls having 5 to 30 nucleus atoms;
m is an integer from 0 to 4;
Ar ₄ to Ar ₆ and R ₁ are each independently a substituent represented by the following formula (4), and when a plurality of R _{1 s} are present, they are the same or different;
(3)

In Formula 3,
* Denotes the part where the bond is made;
L ₁ is selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
R ₂ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting of C ₆₀ aryl amine, the combination group adjacent to form a condensed ring;
Arylene group and a heteroarylene group, an alkyl group of the R ₂ of the L _1, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₁ to C ₄₀ alkyl group, a C ₁ to C ₄₀ alkyl group, an aryl group, ₂ ~ C ₄₀ alkenyl group, an aryloxy group of C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of, C ₁ ~ alkyloxy of C _40, C ₆ ~ C ₆₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ a C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of the O Aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl, aminocarbonyl and resilyl;
[Chemical Formula 4]

In Formula 4,
* Denotes the part where the bond is made;
L ₂ is selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
R ₃ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting of C ₆₀ aryl amine, the combination group adjacent to form a condensed ring;
Arylene group and a heteroarylene group, an alkyl group of the R ₃ of the L _2, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₁ to C ₄₀ alkyl group, a C ₁ to C ₄₀ alkyl group, an aryl group, ₂ ~ C ₄₀ alkenyl group, an aryloxy group of C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of, C ₁ ~ alkyloxy of C _40, C ₆ ~ C ₆₀ aryl amine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl silyl group, C ₁ ~ a C ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of the O A hydroxyl group, a hydroxyl group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group, a cyano group and a resilyl group. The method according to claim 1,
Wherein said compound is represented by the following formula (5):
[Chemical Formula 5]

In Formula 5,
X &lt; _{1 &gt;} and A are each as defined in claim 1. The method according to claim 1,
Wherein X &lt; _{1 &gt;} is S or O. The method according to claim 1,
Wherein said compound is represented by any one of the following formulas (6) to (12):
[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

In the above formulas (6) to (12)
Ar ₁ to Ar ₆ , R ₁ , m and Q ₁ to Q ₂ are each as defined in claim 1. The method according to claim 1,
Wherein A is a substituent represented by the following general formula (13) or (14):
[Chemical Formula 13]

[Chemical Formula 14]

In the above formulas 13 and 14,
* Denotes the part where the bond is made;
Y ₁ , R ₁ and m are each as defined in claim 1. The method according to claim 1,
Wherein L ₁ and L ₂ are each independently a single bond or a linker represented by any one of the following formulas A-1 to A-7:

In the above Formulas A-1 to A-7,
* Denotes the part where the bond is made;
Y ₂ is O or S;
Z ₁ to Z ₃ are each independently N or C (R ₅ );
R ₄ and R ₅ are each independently selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, To 60 heteroaryl groups, and when a plurality of R _{5 s} are present, they are the same as or different from each other;
The alkyl, alkenyl, alkynyl, aryl and heteroaryl groups of R ₄ and R ₅ are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl , A C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, C ₆ ~ aryl of C ₆₀ amine group, a C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl boron in the group, aryl of C ₆ ~ C ₆₀ boron group, C ₆ ~ C ₆₀ aryl phosphazene group, one selected from the group consisting arylsilyl of C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of the And when they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 6,
Wherein R &lt; ₄ &gt; is selected from the group consisting of a phenyl group, a biphenyl group and a naphthalenyl group. The method according to claim 1,
Wherein R ₂ and R ₃ are each independently a substituent represented by any one of the following formulas B-1 to B-4:

In the above B-1 to B-4,
* Denotes the part where the bond is made;
Z ₄ to Z ₈ are each independently N or C (R ₆ );
Y ₃ is selected from the group consisting of S, O, N (Ar ₇ ) and C (Ar ₈ ) (Ar ₉ );
R ₆ and Ar ₇ to Ar ₉ are each independently hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, and a nucleus A heteroaryl group having 5 to 60 atoms, and when R ₆ is plural, they are the same or different;
The alkyl, alkenyl, alkynyl, aryl and heteroaryl groups of R ₆ and Ar ₇ to Ar ₉ are each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl An arylamine group of C ₆ to C ₆₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl boron group, C ₆ ~ aryl of C ₆₀ boron group, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ from the group consisting arylsilyl of C ₆₀ of And when they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 1,
Wherein R ₂ and R ₃ are each independently a substituent represented by any one of the following formulas C-1 to C-10:

In the above formulas C-1 to C-10,
* Denotes the part where the bond is made;
t is an integer from 0 to 5,
u is an integer from 0 to 4;
v is an integer from 0 to 3;
w is an integer from 0 to 2;
R ₇ is heavy hydrogen, 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 ₆ ~ C ₆₀ aryl group, the nucleus of atoms of A C ₆ to C ₆₀ alkyloxy group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryloxy group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ heteroaryl group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, _A C ₆ to C ₆₀ arylamine group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphonyl group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or of, by combining groups of adjacent, may form a fused ring, wherein R ₇ in this case multiple individual which Are the same or different from each other;
Alkyl group of the R _7, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, _A C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ C ₃ to C ₄₀ cycloalkyl groups, 3 to 40 nucleus atom heterocycloalkyl groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ the arylboronic group, one member selected from the group consisting of C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group in the silyl If substituted with a substituent or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other, 10. The method of claim 9,
Wherein R ₂ and R ₃ are each independently a substituent group of the compound represented by any one of the general formula C-1, C-7 and C-10. 10. The method of claim 9,
Wherein R ₇ is selected from the group consisting of a phenyl group, a biphenyl group, a naphthalenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group. The method according to claim 1,
Wherein said compound is selected from the group consisting of:

1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound represented by the general formula (1). 14. The method of claim 13,
Wherein the organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron transporting auxiliary layer, an electron injecting layer, a lifetime improving layer, a light emitting layer and a light emitting auxiliary layer.

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