KR102095449B1 - Organic electroluminescent device - Google Patents

Abstract

The present invention relates to an organic electroluminescent device, and more particularly, to an organic electroluminescent device comprising a novel pyrene-based organic compound and anthracene-based organic compound in at least one organic layer included in the organic electroluminescent device.

Description

Organic electroluminescent device {ORGANIC ELECTROLUMINESCENT DEVICE}

The present invention relates to an organic electroluminescent device, and more particularly, to an organic electroluminescent device comprising a novel pyrene-based organic compound and anthracene-based organic compound in at least one organic layer included in the organic electroluminescent device.

The organic electroluminescent device (OLED) was developed in 1987 by Kodak C.W. Since Tang developed the first organic EL device (CW Tang, SA Vanslyke, Applied Physics Letters, Vol. 51, 913 p. 1987, 1987) using an aluminum compound as an aromatic diamine as a light emitting layer, multi-layer thin-film structured organic electroluminescence Research into devices and organic materials has been actively conducted. The organic light emitting device has a simple structure and has various advantages in a manufacturing process compared to other flat panel display devices such as a liquid crystal display (LCD), a plasma display panel (PDP), and a field emission display (FED), and has high brightness and viewing angle. It has excellent characteristics, has a fast response speed, and has a low driving voltage, and has been commercialized as a light source for flat panel displays such as wall-mounted TVs or backlights of displays, lights and billboards.

In general, an organic light emitting device is a device that emits light when holes and electrons meet and emit light in a light emitting layer when a voltage is applied to a cathode (electron injection electrode) and an anode (hole injection electrode). It has a structure comprising an organic layer. At this time, the organic light emitting device, in addition to the light emitting layer (EML, Light Emitting Layer), hole injection layer (HIL, Hole Injection Layer), hole transport layer (HTL, Hole Transport Layer), electron transport layer (ETL, Electron Transport Layer) or electron injection A layer (EIL, Electron Injection Layer) may be included, and an electron blocking layer (EBL, Electron Blocking Layer) or a hole blocking layer (HBL) may be additionally included to increase the efficiency of the light emitting layer. have. The organic electroluminescent device including all of these organic layers has a structure stacked in the order of anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode.

On the other hand, when only one material is used as the light emitting material used in the light emitting layer, the maximum light emission wavelength moves to a long wavelength due to intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the light attenuation effect. Therefore, a host / dopant system may be used as a light emitting material to increase color purity and increase light emission efficiency through energy transfer.

The principle is that when a small amount of the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with the light emitting layer, exciton generated in the light emitting layer is transported as a dopant to produce light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of a desired wavelength can be obtained according to the type of the dopant used.

The light emitting layer is composed of a red host / dopant, a green host / dopant, and a blue host / dopant, respectively, and the blue light emitting layer is a host and a dopant capable of realizing excellent blue color for the greatest inferiority in life, efficiency and color purity compared to other colors. Development is required.

Recently, it is important for blue hosts to replace polar derivatives such as Dibenzofuran in existing polyaromatic systems. The reason is that the polarity and dipole moment increase due to the oxygen molecules contained in the dibenzofuran. These characteristics increase the packing of the host molecule in the device, thereby improving the driving voltage and efficiency of the device and increasing the life of the device. However, despite these characteristics, it is important to find the ideal host / dopant combination because the blue light dopant used in the related art has a phenomenon in which the maximum emission wavelength shifts to a long wavelength (red) when the polarity of the host increases.

An object of the present invention is to provide a host / dopant system that minimizes the phenomenon that the maximum emission wavelength moves to a long wavelength (red) when a compound contained in Dibenzofuran is used as a host, resulting in excellent color purity, low driving voltage, high It is an object to provide an organic electroluminescent device having characteristics such as luminous efficiency and long life.

The terminology used herein is used to describe a specific embodiment and is not intended to limit the present invention. As used herein, singular forms may include plural forms unless the context clearly indicates otherwise. Also, as used herein, “comprise” and / or “comprising” specifies the shapes, numbers, steps, actions, elements, elements and / or the presence of these groups. And does not exclude the presence or addition of one or more other shapes, numbers, actions, elements, elements and / or groups.

As used herein, the term “and / or” includes any and all combinations of one or more of the listed items.

In the present invention, “alkyl” means a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples of this include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

In the present invention, "alkenyl (alkenyl)" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon double bonds. Examples of this include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

In the present invention, "alkynyl (alkynyl)" means 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 of this include ethynyl, 2-propynyl, and the like, but are not limited thereto.

In the present invention, “aryl” refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, a form in which two or more rings are simply attached to each other or condensed may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, dimethylfluorenyl, and the like.

In the present invention, "heteroaryl" means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, 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 simply attached to each other or condensed may be included, and condensed form with an aryl group may also be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, and indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, and 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 6 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, and the like, but are not limited thereto.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means alkyl having 1 to 40 carbon atoms, and has a 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.

In the present invention, "arylamine" means an amine substituted with aryl having 6 to 60 carbon atoms.

“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 the cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

In the present invention, “heterocycloalkyl” refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and 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 morpholine, piperazine, and the like, but are not limited thereto.

In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” refers to silyl substituted with aryl having 6 to 60 carbon atoms.

In the present invention, “condensed ring” means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

In order to achieve the above object, the first electrode; A second electrode; And an organic electroluminescent device comprising at least one organic film between the first electrode and the second electrode, wherein the organic film is a light emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection. It includes at least one layer selected from the group consisting of a layer, the light emitting layer provides an organic electroluminescent device comprising a compound represented by the following formula (1) and a compound represented by the following formula (2):

[Formula 1]

here,

L ₁ includes C ₁ , C ₂ and C ₃ to form a saturated or unsaturated condensed ring of C ₄ to C ₇ , and the ring may be substituted with C ₁ to C ₁₀ alkyl,

R ₁ to R ₈ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, nitro group _, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alke having 2 to 30 carbon atoms A C 2 to C 30 substituted or unsubstituted carbon atom Alkynyl group, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms of An aryl group, substituted or unsubstituted, having 6 to 30 carbon atoms Heteroaryl group, substituted or unsubstituted 6 to 30 carbon atoms A heteroaryl alkyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms,

[Formula 2]

here,

R ₁₁ to R ₂₀ are the same as or different from each other, and at least one is -L ₂ -Ar ₁ And / or -L ₃ -Ar ₂ ,

L ₂ and L ₃ are the same or different from each other, and each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 6 to 30 nuclear atoms, a substituted or unsubstituted carbon number. 2 to 10 alkylene groups, substituted or unsubstituted cycloalkylene groups having 2 to 10 carbon atoms, substituted or unsubstituted alkenylene groups having 2 to 10 carbon atoms, substituted or unsubstituted cycloalkenylene groups having 2 to 10 carbon atoms, substituted or unsubstituted Heteroalkylene group having 2 to 10 carbon atoms, substituted or unsubstituted heterocycloalkylene group having 2 to 10 carbon atoms, substituted or unsubstituted heteroalkenylene group having 2 to 10 carbon atoms and substituted or unsubstituted heterocycloalkenylene having 2 to 10 carbon atoms Is selected from the group consisting of

Ar ₁ and Ar ₂ are the same or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. , A substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, A substituted or unsubstituted cycloalkenyl group having 1 to 20 carbon atoms and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms,

-L ₂ -Ar ₁ Or R ₁₁ to R ₂₀ other than -L ₃ -Ar ₂ are the same or different from each other, and each independently hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms , Substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted Or an unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and a substituted or unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms,

R ₁ to R _8, L ₂ to L ₃ , Ar ₁ to Ar ₂ and R ₁₁ to R ₂₀ are each independently hydrogen, deuterium, cyano group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted Alkynyl group having 2 to 24 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted carbon number Aryl group having 6 to 30, substituted or heteroaryl group having 2 to 30 carbon atoms, substituted or unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted carbon number 1 to 30 alkylamino group, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms are Chelamino group, substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms and substituted or unsubstituted 6 to 30 carbon atoms It may be further substituted with one or more substituents selected from the group consisting of aryloxy groups, and when the number of substituents is plural, they are the same or different from each other.

In one embodiment of the present invention, the compound represented by Formula 1 represents a compound represented by Formula 3 below.

[Formula 3]

here,

R ₉ and R ₁₀ are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, a substituted or unsubstituted carbon atom having 1 to 10 carbon atoms, It is selected from the group consisting of an alkoxy group, a halogen, a cyano group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, and an arylsilyl group having 6 to 30 carbon atoms,

R ₉ and R ₁₀ are each independently hydrogen, deuterium, urethane group, carboxyl group, cyano group, nitro group, halogen group, hydroxy group, carboxylate group, alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms , An alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, and one or more substituents selected from the group consisting of a heteroalkyl group having 2 to 30 carbon atoms, and when the substituents are plural, Same or different,

n is an integer from 1 to 3,

R ₁ to R ₈ are as defined in claim 1.

In one embodiment of the present invention, any one of R ₁ to R ₈ of Formula 1 represents a functional group represented by Formula 4 below.

[Formula 4]

[Formula 5]

here,

L is a single bond, a substituted or unsubstituted C ₆ -C ₁₈ arylene group, or a substituted or unsubstituted C ₆ -C ₁₈ heteroarylene group,

M is hydrogen, deuterium, or a functional group represented by Formula 5 above,

Ar ₃ and Ar ₄ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted Alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon having 2 to 24 carbon atoms Alkynyl group, a substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted carbon having 6 to 30 carbon atoms Aryl group, substituted or unsubstituted, having 2 to 30 carbon atoms A heteroaryl group, a substituted or unsubstituted C ₆ -C ₃₀ heteroarylalkyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms and an arylsilyl group having 6 to 30 carbon atoms, or Ar ₃ and Ar ₄ Is connected to each other, may form a ring of 6 to 18 members including one or more N, O or S,

The L, Ar ₃ and Ar ₄ are each independently hydrogen, deuterium, urethane group, carboxy group, cyano group, nitro group, halogen group, hydroxy group, carboxylate group, 1 to 30 carbon atoms alkyl group, 2 to 30 carbon atoms Alkenyl group, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 30 carbon atoms, heteroalkyl group having 2 to 30 carbon atoms, aralkyl group having 7 to 30 carbon atoms, aryl group having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms Group, a heteroaryl alkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, a hetero group having 2 to 24 carbon atoms At least one substituent selected from the group consisting of arylamino groups, alkylsilyl groups having 1 to 30 carbon atoms, arylsilyl groups having 6 to 30 carbon atoms, and aryloxy groups having 6 to 30 carbon atoms. Horizontal may be substituted and, in the case where the substituent is plural, they are the same as or different from each other.

In one embodiment of the present invention, Ar ₃ and Ar ₄ in Chemical Formula 5 represent a substituent selected from the group consisting of compounds represented by the following Chemical Formulas 6 to 11.

 [Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

here,

* Is the part where the bond is made,

p is an integer from 0 to 4,

q is an integer from 0 to 3,

X ₁ is selected from the group consisting of C (R ₂₃ ), N, S and O,

X ₂ , X ₃ , X ₄ and X ₆ are the same as or different from each other, and each independently, are selected from the group consisting of C (R ₂₃ ) (R ₂₄ ), N (R ₂₃ ), S and O,

X ₅ and X ₇ are the same as or different from each other, and each independently C (R ₂₃ ) or N,

R ₂₁ to R ₂₄ are the same or different from each other, and each independently independently independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted 3 to 30 carbon atoms Cycloalkyl group, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon having 2 to 24 carbon atoms Alkynyl group, a substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted carbon having 6 to 30 carbon atoms Aryl group, substituted or unsubstituted, having 2 to 30 carbon atoms A heteroaryl group, a substituted or unsubstituted C ₆ -C ₃₀ heteroarylalkyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms and arylsilyl group having 6 to 30 carbon atoms,

Each of R ₂₁ to R ₂₄ is independently hydrogen, deuterium, urethane group, carboxy group, cyano group, nitro group, halogen group, hydroxy group, carboxylate group, alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms , An alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, Heteroarylalkyl group having 3 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, alkylamino group having 1 to 30 carbon atoms, arylamino group having 6 to 30 carbon atoms, aralkylamino group having 6 to 30 carbon atoms, hetero arylamino group having 2 to 24 carbon atoms , One or more substituents selected from the group consisting of an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms Horizontal may be substituted and, in the case where the substituent is plural, they are the same as or different from each other.

In one embodiment of the present invention, when M is a functional group represented by Chemical Formula 5, Ar ₃ and Ar ₄ Represents a compound represented by any one of the following formulas (12) or (13) by connecting with N of M to form a ring.

[Formula 5]

[Formula 12]

[Formula 13]

here,

X ₈ and X ₉ are the same as or different from each other, and each independently selected from the group consisting of C (R ₂₅ ) (R ₂₆ ), N (R ₂₅ ), C, N, O and S,

R ₂₅ and R ₂₆ are the same or different from each other, and each independently independently independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted 3 to 30 carbon atoms. Cycloalkyl group, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon having 2 to 24 carbon atoms Alkynyl group, a substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted carbon having 6 to 30 carbon atoms Aryl group, substituted or unsubstituted, having 2 to 30 carbon atoms A heteroaryl group, a substituted or unsubstituted C ₆ -C ₃₀ heteroarylalkyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms and arylsilyl group having 6 to 30 carbon atoms, or

Each of R ₂₅ to R ₂₆ is independently hydrogen, deuterium, urethane group, carboxy group, cyano group, nitro group, halogen group, hydroxy group, carboxylate group, alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms , An alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, Heteroarylalkyl group having 3 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, alkylamino group having 1 to 30 carbon atoms, arylamino group having 6 to 30 carbon atoms, aralkylamino group having 6 to 30 carbon atoms, heteroaryl amino group having 2 to 24 carbon atoms , One or more substituents selected from the group consisting of an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms Horizontal may be substituted and, in the case where the substituent is plural, they are the same as or different from each other.

In one embodiment of the present invention, the compound represented by Formula 2 represents a compound represented by Formula 14 below.

[Formula 14]

here,

R ₁ to R ₈ , Ar ₁ to Ar ₂ And L ₂ to L ₃ are as defined in claim 1.

In one embodiment of the present invention, L ₂ and L ₃ in Formula 14 are the same as or different from each other, and each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted nuclear atom number 6 To 30 heteroarylene groups, an organic electroluminescent device.

In one embodiment of the present invention, at least one or more of Ar ₁ and Ar ₂ of Formula 14 represents a compound represented by Formula 15 below.

[Formula 15]

here,

R ₂₇ to R ₃₄ are the same as or different from each other, and at least one is -L ₂ -Ar ₁ And / or -L ₃ -Ar ₂ ,

X is O or S,

-L ₂ -Ar ₁ And / or R ₂₇ to R ₃₄ other than -L ₃ -Ar ₂ are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted 2 to 24 carbon atoms Alkynyl group, a substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted carbon having 6 to 30 carbon atoms Aryl group, substituted or unsubstituted, having 2 to 30 carbon atoms Heteroaryl group, a substituted or unsubstituted C ₆ -C ₃₀ heteroarylalkyl group is selected from the group consisting of substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms and arylsilyl group having 6 to 30 carbon atoms, and saturated or unsaturated together with adjacent groups. Condensed rings can be further formed,

Each of R ₂₇ to R ₃₄ and the saturated or unsaturated condensed ring formed by them are each independently hydrogen, deuterium, urethane group, carboxy group, cyano group, nitro group, halogen group, hydroxy group, carboxylate group, carbon number 1 Alkyl group having 30 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 30 carbon atoms, heteroalkyl group having 2 to 30 carbon atoms, aralkyl group having 7 to 30 carbon atoms, 6 to 30 carbon atoms Aryl group, heteroaryl group having 2 to 30 carbon atoms, heteroarylalkyl group having 3 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, alkylamino group having 1 to 30 carbon atoms, arylamino group having 6 to 30 carbon atoms, 6 to 30 carbon atoms Aralkylamino group, heteroaryl amino group having 2 to 24 carbon atoms, alkylsilyl group having 1 to 30 carbon atoms, arylsilyl group having 6 to 30 carbon atoms and aryloxy group having 6 to 30 carbon atoms It may be further substituted with one or more substituents selected from the group consisting of, if the plurality of substituents, they are the same or different from each other.

In one embodiment of the present invention, Formula 15 represents a compound represented by Formulas 16 to 24 below.

[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

[Formula 22]

[Formula 23]

[Formula 24]

here,

X is O or S,

e is an integer from 0 to 6,

f is an integer from 0 to 6,

g is an integer from 0 to 4,

h is an integer from 0 to 4,

R ₃₅ to R ₃₇ are the same as or different from each other, and each independently a single bond, hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted 3 to 30 carbon atoms Cycloalkyl group, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon having 2 to 24 carbon atoms Alkynyl group, a substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted carbon having 6 to 30 carbon atoms Aryl group, substituted or unsubstituted, having 2 to 30 carbon atoms A heteroaryl group, a substituted or unsubstituted C ₆ -C ₃₀ heteroarylalkyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms and arylsilyl group having 6 to 30 carbon atoms,

Any one of R ₃₅ to R ₃₇ is combined with L ₂ or L ₃ .

In one embodiment of the present invention, R ₁₁ to R ₁₈ are the same as or different from each other, and each independently hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cyclo group having 3 to 30 carbon atoms Alkyl group and substituted or unsubstituted 6 to 30 carbon atoms Aryl group.

In one embodiment of the present invention, the compound represented by Formula 1 is selected from the group consisting of the following compounds:

In one embodiment of the present invention, the compound represented by Formula 2 is selected from the group consisting of the following compounds:

According to an embodiment of the present invention, the light emitting layer of the organic light emitting device of the present invention includes a dopant and a host, the dopant includes a compound represented by Formula 1, and the host is a compound represented by Formula 2 It may include.

The organic compound represented by Chemical Formula 1 of the present invention may be used as a dopant material, and is preferably a blue dopant material. Specifically, the organic compound is a blue dopant material, thereby providing a dark blue host / dopant system suitable for AM-OLED by shifting the emission wavelength toward a shorter wavelength of 7 nm or more compared to a conventional blue dopant.

The organic compound represented by Chemical Formula 1 of the present invention interferes with the formation of an excimer of a dopant by introducing an alkyl group of a cyclic compound into the pyrene molecular core, thereby increasing the electron density of the core and the stability of the dopant. Increases the efficiency and lifespan.

The organic compound represented by Chemical Formula 1 of the present invention has excellent solubility in a solution, and thus has an easy property in manufacturing a solution process OLED device, and reduces the production process cost.

One embodiment of the present invention provides a material for forming a light emitting layer comprising an organic compound represented by Formula 1 and an organic compound represented by Formula 2. The material for forming the light emitting layer may include a commonly added material, for example, a known dopant and a host material.

In one embodiment of the present invention, the host material may be an organic compound represented by Chemical Formula 2, but is not limited to examples.

According to another embodiment of the present invention, in the organic light emitting device in which an organic thin film layer comprising at least one layer or a plurality of layers including at least a light emitting layer is laminated between a cathode and an anode, the light emitting layer is an organic compound represented by the formula (1) and An organic electroluminescent device comprising a compound represented by Formula 2 is provided.

In one embodiment of the present invention, the organic electroluminescent device of the present invention is an anode (hole injection electrode), hole injection layer (HIL), hole transport layer (HTL), light emitting layer (EML) and cathode (electron injection electrode) sequentially It may have a stacked structure, and preferably, may further include an electron blocking layer (EBL) between the anode and the emission layer, and an electron transport layer (ETL) and an electron injection layer (EIL) between the cathode and the emission layer. . In addition, a hole blocking layer (HBL) may be further included between the cathode and the light emitting layer. Hereinafter, the organic electroluminescent device of the present invention will be described as an example. However, the contents exemplified below do not limit the organic electroluminescent device of the present invention.

In another embodiment of the present invention, a method for manufacturing an organic electroluminescent device according to the present invention is provided, but the contents illustrated below do not limit the method for manufacturing the organic electroluminescent device of the present invention.

Specifically, first, a positive electrode is formed on the surface of the substrate by coating a material for a positive electrode in a conventional manner. At this time, the substrate used is preferably a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling and waterproofness. In addition, as the material for the anode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, may be used.

Next, a hole injection layer (HIL) material is vacuum-deposited or spin coated on the anode surface in a conventional manner to form a hole injection layer. Examples of the hole injection layer material include copper phthalocyanine (CuPc), 4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine (m-MTDATA), 4,4', 4" -tris (3-methylphenyl) Amino) phenoxybenzene (m-MTDAPB), starburst amines 4,4 ', 4 "-tri (N-carbazolyl) triphenylamine (TCTA), 4,4', 4" -tris Examples include (N- (2-naphthyl) -N-phenylamino) -triphenylamine (2-TNATA) or IDE406 available from Idemitsu.

A hole transport layer (HTL) material is vacuum-deposited or spin coated on the surface of the hole injection layer in a conventional manner to form a hole transport layer. At this time, as the hole transport layer material, bis (N- (1-naphthyl-n-phenyl)) benzidine (α-NPD), N, N'-di (naphthalen-1-yl) -N, N'-biphenyl -Benzidine (NPB) or N, N'-biphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl-4,4'-diamine (TPD).

A light emitting layer (EML) material is vacuum-deposited or spin coated on the surface of the hole transport layer in a conventional manner to form a light emitting layer. At this time, the like of the light-emitting layer material to be used as the sole light emitting material or light emitting host material, but the compound represented by the general formula (2) may preferably be used, in the case of green-tris (8-hydroxy-quinolinolato) aluminum (Alq ₃₎ Can be used, in the case of blue, Balq (8-hydroxyquinoline beryllium salt), DPVBi (4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl), Spiro ) Substance, spiro-DPVBi (spiro-4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzooxazolyl) -phenol lithium salt ), Bis (biphenylvinyl) benzene, aluminum-quinoline metal complexes, metal complexes of imidazole, thiazole and oxazole.

In the case of a dopant that can be used together with a light emitting host among the light emitting layer materials, the organic compound represented by Formula 1 of the present invention can be preferably used as a blue fluorescent dopant, IDE102, available from Idemitsu as another fluorescent dopant, IDE105, tris (2-phenylpyridine) iridium (III) (Ir (ppy) 3), iridium (III) bis [(4,6-difluorophenyl) pyridinato-N, C-2 as phosphorescent dopant '] Picolinate (FIrpic) (Chihaya Adachi et al., Appl. Phys. Lett., 2001, 79, 3082-3084), Platinum (II) octaethylporphyrin (PtOEP), TBE002 ) And the like.

Alternatively, an electron blocking layer (EBL) may be additionally formed between the hole transport layer and the light emitting layer.

An electron transport layer (ETL) material is vacuum-deposited or spin coated on the surface of the light emitting layer in a conventional manner to form an electron transport layer. In this case, the electron transport layer material used is not particularly limited, and preferably tris (8-hydroxyquinolinolato) aluminum (Alq ₃ ) can be used.

Alternatively, by forming a hole blocking layer (HBL) between the light emitting layer and the electron transport layer and using a phosphorescent dopant and a light emitting host together in the light emitting layer, it is possible to prevent a phenomenon in which triplet excitons or holes diffuse into the electron transport layer. The phosphorescent dopant may be an organic compound represented by Chemical Formula 1, and the light-emitting host may be an organic compound represented by Chemical Formula 2.

The hole blocking layer may be formed by vacuum thermal evaporation and spin coating of the hole blocking layer material in a conventional manner, and the hole blocking layer material is not particularly limited, but preferably (8-hydroxyquinolinola) Lithium (Liq), bis (8-hydroxy-2-methylquinolinolnato) -aluminum biphenoxide (BAlq), bathocuproine (BCP), LiF, and the like can be used.

An electron injection layer (EIL) material is vacuum-deposited or spin coated on the surface of the electron transport layer in a conventional manner to form an electron injection layer. At this time, as the electron injection layer material used, materials such as LiF, Liq, Li ₂ O, BaO, NaCl, and CsF may be used.

A negative electrode is formed on the surface of the electron injection layer by vacuum thermal vapor deposition of a material for a negative electrode in a conventional manner. At this time, the negative electrode material used is lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and the like can be used. In addition, in the case of a front emission organic electroluminescent device, a transparent cathode through which light can pass may be formed using indium tin oxide (ITO) or indium zinc oxide (IZO).

A capping layer (CPL) may be formed on the surface of the cathode by the composition for forming a capping layer of the present invention.

According to the present invention, an organic electroluminescent device including an organic compound capable of sublimation and deposition even at a low temperature, realizing a darker blue color, and increasing efficiency and lifetime of the device is provided.

In addition, according to the present invention, an organic compound containing an organic compound capable of solving the productivity and cost problems of the existing blue dopant material and easily implementing a device in a solution process other than a deposition process that must be carried out in an existing OLED process An electroluminescent element is provided.

In addition, according to the present invention, a deep blue-based blue host / dopant system suitable for AM-OLED is provided, and as a result, an organic electroluminescent device having characteristics such as low driving voltage, high luminous efficiency, and long life is provided. do.

1 is NMR data of the intermediate 1-A compound.

The embodiments of the present invention are provided to more fully describe the present invention to those of ordinary skill in the art, and the following embodiments can be modified in various other forms, and the scope of the present invention is as follows. It is not limited to the Examples. Rather, these examples are provided to make the present disclosure more faithful and complete, and to fully convey the spirit of the present invention to those skilled in the art.

Hereinafter, a method for synthesizing the compounds represented by Chemical Formula 1 will be described below as a representative example. However, the method for synthesizing the compounds of the present invention is not limited to the methods exemplified below, and the compounds of the present invention can be prepared by the methods exemplified below and methods known in the art.

<Synthesis example>

Synthesis of Intermediate 1-A

After dissolving 288.4 g (1 mol) of 2-methyl-4- (pyren-1-yl) butan-2-ol in 2.8 L of toluene, 10 wt% of acid was added. While removing moisture using a Dean-Stark device, the mixture was stirred in a heated / reflux state for 12 hours. After confirming the completion of the reaction, 10 L of water was added to extract the toluene layer, and then the toluene layer was extracted again with 1 L of water. The extracted solution was treated with MgSO ₄ to remove residual moisture, and dried in a vacuum oven. Thereafter, column purification was performed with n-hexane to obtain 192.0 g of Compound A in a yield of 71%.

Synthesis Example 1-1

Synthesis of Compound 1-1

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and N- (5- (tert-butyl) After dissolving 8.02 g (30 mmol) of 2-methylphenyl) -2,4-dimethylaniline in 100 ml of toluene, NaOtBu 5.76 g (60.0 mmol), Pd ₂ (dba) 3 0.46 g (0.5 mmol), tBu ₃ P 0.2 g ( 1.0mmol) was added and stirred for 6 hours under heating / reflux. After confirming the completion of the reaction, 100 ml of water was added to extract the toluene layer, and then 50 ml of water was added to extract the toluene layer again. The extracted solution was treated with MgSO ₄ to remove residual moisture and dried in a vacuum oven. Then, column purification was performed with n-hexane / MC to obtain 5.06 g of 'Compound 1-1' in a yield of 60%.

MS (MALDI-TOF) m / z: 843 [M] +

Synthesis Example 1-2

Synthesis of Compound 1-2

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and N- (5- (tert-butyl) 2-methylphenyl) -2,4-dimethylaniline 8.02g (30mmol) instead of 1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd ] 4.93 g of 'Compound 1-2' was reacted in the same manner as in Synthesis Example 1-1, except that 4.70 g (10.0 mmol) of pyrene and 6.76 g (30 mmol) of bis (2,4-dimethylphenyl) amine were used. Obtained with a yield of 65%.

MS (MALDI-TOF) m / z: 759 [M] +

Synthesis Example 1-3

Synthesis of Compound 1-3

4.42 g (10.0 mmol) of 1,7-dibromo-5,5,9-trimethyl-4,5-dihydro-3H-benzo [cd] pyrene and N- (5- (tert-butyl) -2- Reaction was performed in the same manner as in Synthesis Example 1-1, except that 8.02 g (30 mmol) of methylphenyl) -2,4-dimethylaniline was obtained to obtain 5.05 g of 'Compound 1-3' in a yield of 62%.

MS (MALDI-TOF) m / z: 815 [M] +

Synthesis Example 1-4

Synthesis of Compound 1-4

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and 5- (tert-butyl) -2- Reaction was carried out in the same manner as in Synthesis Example 1-1, except that 7.60 g (30 mmol) of methyl-N- (o-tolyl) aniline was used to obtain 4.64 g of 'Compound 1-4' in a yield of 57%.

MS (MALDI-TOF) m / z: 815 [M] +

Synthesis Example 1-5

Synthesis of Compound 1-5

4.70 g (10.0 mmol) of 1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene and 2,6-dimethyl-N- (4 -(Methyltrimethylsilyl) phenyl) aniline 8.08g (30mmol), except that the reaction in the same manner as in Synthesis Example 1-1 to obtain 6.35g of 'Compound 1-5' in 75% yield.

MS (MALDI-TOF) m / z: 847 [M] +

Synthesis Example 1-6

Synthesis of Compound 1-6

1, 1,7-dibromo-5,5,9-methyltrimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.42g (10.0mmol) and 5- (tert-butyl) -N- Reaction was performed in the same manner as in Synthesis Example 1-1, except that (2,5-dimethylphenyl) -2-methylaniline 8.02 g (30 mmol) was used to obtain 5.30 g of 'Compound 1-6' in a yield of 65%. .

MS (MALDI-TOF) m / z: 815 [M] +

Synthesis Example 1-7

Synthesis of Compound 1-7

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and 4- (tert-butyl) -2, Reaction was carried out in the same manner as in Synthesis Example 1-1, except that 6.60 g (30 mmol) of 6-dimethyl-N-phenylaniline was used to obtain 4.64 g of 'Compound 1-7' in a yield of 57%.

MS (MALDI-TOF) m / z: 815 [M] +

Synthesis Example 1-8

Synthesis of Compound 1-8

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and N- (4- (tert-butyl) Reaction was conducted in the same manner as in Synthesis Example 1-1, except that 7.60 g (30 mmol) of phenyl) -2,6-dimethylaniline was obtained, and 4.97 g of 'Compound 1-8' was obtained in a yield of 61%.

MS (MALDI-TOF) m / z: 815 [M] +

Synthesis Example 1-9

Synthesis of Compound 1-9

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and 5- (tert-butyl) -N- Reaction was performed in the same manner as in Synthesis Example 1-1, except that (2,5-dimethylphenyl) -2-methylaniline 8.02 g (30 mmol) was used to obtain 5.56 g of 'Compound 1-9' in a yield of 66%. .

MS (MALDI-TOF) m / z: 843 [M] +

Synthesis Example 1-10

Synthesis of Compound 1-10

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and N- (3,5-dimethylphenyl) -2,6-Dimethylaniline 6.76 g (30 mmol) was reacted in the same manner as in Synthesis Example 1-1, except that 4.48 g of 'Compound 1-10' was obtained in a yield of 59%.

MS (MALDI-TOF) m / z: 759 [M] +

Synthesis Example 1-11

Synthesis of Compound 1-11

1,7-dibromo-5,5,9-methyltrimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.42g (10.0mmol) and N- (4-isopropylphenyl) dibenzo [ b, d] Reaction was carried out in the same manner as in Synthesis Example 1-1, except that 9.04 g (30 mmol) of furan-3-amine was used to obtain 5.74 g of 'Compound 1-11' in a yield of 65%.

MS (MALDI-TOF) m / z: 883 [M] +

Synthesis Example 1-12

Synthesis of Compound 1-12

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and N- (4-isopropylphenyl) di Reaction was carried out in the same manner as in Synthesis Example 1-1, except that 9.04 g (30 mmol) of benzo [b, d] furan-3-amine was used to obtain 6.38 g of 'Compound 1-12' in a yield of 70%.

MS (MALDI-TOF) m / z: 911 [M] +

Synthesis Example 1-13

Synthesis of Compound 1-13

4.70 g (10.0 mmol) of 1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene and N- (1,1'-biphenyl ] -2-yl) dibenzo [b, d] furan-3-amine 9.46g (30mmol) was reacted in the same manner as in Synthesis Example 1-1, except that 5.09g of 'Compound 1-13' was 52 % Yield.

MS (MALDI-TOF) m / z: 979 [M] +

Synthesis Example 1-14

Synthesis of Compound 1-14

4.42 g (10.0 mmol) of 1,7-dibromo-5,5,9-methyltrimethyl-4,5-dihydro-3H-benzo [cd] pyrene and N- (4- (tert-butyl) phenyl) Reaction was performed in the same manner as in Synthesis Example 1-1, except that 9.46 g (30 mmol) of dibenzo [b, d] furan-3-amine was used to obtain 6.01 g of 'Compound 1-14' in a yield of 66%.

MS (MALDI-TOF) m / z: 911 [M] +

Synthesis Example 1-15

Synthesis of Compound 1-15

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and N- (2-isopropylphenyl) di Reaction was carried out in the same manner as in Synthesis Example 1-1, except that 9.04 g (30 mmol) of benzo [b, d] furan-3-amine was used to obtain 4.10 g of 'Compound 1-15' in a yield of 45%.

MS (MALDI-TOF) m / z: 911 [M] +

Synthesis Example 1-16

Synthesis of Compound 1-16

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and N- (o-Tolyl) dibenzo [ b, d] Reaction was carried out in the same manner as in Synthesis Example 1-1, except that 8.32 g (30 mmol) of furan-3-amine was used to obtain 4.70 g of 'Compound 1-16' in a yield of 55%.

MS (MALDI-TOF) m / z: 855 [M] +

Synthesis Example 1-17

Synthesis of Compound 1-17

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and Diphenylamine 5.08g (30mmol) were used. Reaction was conducted in the same manner as in Synthesis Example 1-1, except that 4.98 g of 'Compound 1-17 ' was obtained in a yield of 77%.

. MS (MALDI-TOF) m / z: 646 [M] +

Synthesis Example 1-18

Synthesis of Compound 1-18

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and bis (4-Fluorophenyl) amine 6.16g (30 mmol) was reacted in the same manner as in Synthesis Example 1-1, except that 4.74 g of 'Compound 1-18' was obtained in a yield of 66%.

MS (MALDI-TOF) m / z: 718 [M] +

Synthesis Example 1-19

Synthesis of Compound 1-19

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and di ([1,1'-biphenyl ] -4-yl) Reaction was carried out in the same manner as in Synthesis Example 1-1, except that 9.64 g (30 mmol) of amine was used to obtain 5.99 g of 'Compound 1-19' in a yield of 63%.

MS (MALDI-TOF) m / z: 951 [M] +

Synthesis Example 1-20

Synthesis of Compound 1-20

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and N-([1,1'-ratio Phenyl] -4-yl) naphthalen-1-amine 8.85 g (30 mmol) was reacted in the same manner as in Synthesis Example 1-1, to obtain 3.14 g of 'Compound 1-20' in a yield of 42%.

MS (MALDI-TOF) m / z: 899 [M] +

Synthesis Example 1-21

Synthesis of Compound 1-21

4.70 g (10.0 mmol) of 1,7 dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene and N-phenyldibenzo [b, d] thiophen Reaction was carried out in the same manner as in Synthesis Example 1-1, except that 8.26 g (30 mmol) of -4-amine was used to obtain 5.50 g of 'Compound 1-21' in a yield of 64%.

MS (MALDI-TOF) m / z: 859 [M] +

Synthesis Example 1-22

Compound 1-22 Synthesis of

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and N-phenylpyridin-3-amine 5.11g (30 mmol) was reacted in the same manner as in Synthesis Example 1-1, except that 2.14 g of 'Compound 1-22 ' was obtained in a yield of 33%.

MS (MALDI-TOF) m / z: 648 [M] +

Synthesis Example 1-23

Synthesis of Compound 1-23

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and N-phenyl-4- (trifluoromethyl) Reaction was conducted in the same manner as in Synthesis Example 1-1, except that 7.12 g (30 mmol) of aniline was used, thereby obtaining 3.52 g of 'Compound 1-23' in a yield of 45%.

MS (MALDI-TOF) m / z: 782 [M] +

Synthesis Example 1-24

Synthesis of Compound 1-24

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and 9,9-dimethyl-N-phenyl- Reaction was performed in the same manner as in Synthesis Example 1-1, except that 8.56 g (30 mmol) of 9H-fluoren-1-amine was used to obtain 5.28 g of 'Compound 1-24' in a yield of 60%.

MS (MALDI-TOF) m / z: 879 [M] +

Synthesis Example 1-25

Synthesis of Compound 1-25

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and bis (4-methoxyphenyl) amine 6.88 Reaction was conducted in the same manner as in Synthesis Example 1-1, except that g (30 mmol) was used to obtain 5.45 g of 'Compound 1-25' in a yield of 71%.

MS (MALDI-TOF) m / z: 766 [M] +

Synthesis Example 1-26

Synthesis of Compound 1-76

1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene 4.70g (10.0mmol) and 2,6-dimethyl-N-phenylamine Reaction was performed in the same manner as in Synthesis Example 1-1, except that 5.91 g (30 mmol) was used, to obtain 4.85 g of 'Compound 1-76' in a yield of 71%.

MS (MALDI-TOF) m / z: 702 [M] +

Synthesis Example 1-27

Synthesis of Compound 1-77

4.70 g (10.0 mmol) of 1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene and 2,6-dimethyl-N- (o -Reaction was carried out in the same manner as in Synthesis Example 1-1, except that 5.91 g (30 mmol) of tolylamine was used to obtain 4.67 g of 'Compound 1-77' in a yield of 64%.

MS (MALDI-TOF) m / z: 731 [M] +

Synthesis Example 2-1

Synthesis of Compound 2-1

9-bromo-10-phenylanthracene (3.33 g, 10 mmol) and dibenzofuran-4-boronic acid (2.33 g, 11 mmol), potassium carbonate (2.76 g, 20 mmol), toluene 50 mL, water 10 mL , Add 10 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized from toluene to obtain 2.45 g (63%) of Compound 2-1.

MS (MALDI-TOF) m / z: 420 [M] +

Synthesis Example 2-2

Synthesis of Compound 2-2

9-bromo-10-phenylanthracene (3.33 g, 10 mmol) and dibenzofuran-3-boronic acid (2.33 g, 11 mmol), potassium carbonate (2.76 g, 20 mmol), toluene 50 mL, water 10 mL , Add 10 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized from toluene to obtain 2.81 g (67%) of Compound 2-2.

MS (MALDI-TOF) m / z: 420 [M] +

Synthesis Example 2-3

Synthesis of Compound 2-3

9-bromo-10-phenylanthracene (3.33 g, 10 mmol) and dibenzofuran-2-boronic acid (2.33 g, 11 mmol), potassium carbonate (2.76 g, 20 mmol), toluene 50 mL, water 10 mL , Add 10 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized from toluene to obtain 2.73 g (65%) of compound 2-3.

MS (MALDI-TOF) m / z: 420 [M] +

Synthesis Example 2-4

Synthesis of Compound 2-4

9-bromo-10-phenylanthracene (33.3 g, 10 mmol) and dibenzofuran-1-boronic acid (2.33 g, 11 mmol) potassium carbonate (2.76 g, 20 mmol), toluene 50 mL, water 10 mL, Add 10 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Then, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized from toluene to obtain 2.77 g (66%) of Compound 2-4.

MS (MALDI-TOF) m / z: 420 [M] +

Synthesis Example 2-5

Synthesis of Compound 2-5

9-bromo-10-phenylanthracene (3.33 g, 10 mmol) and dibenzofuran-6-phenyl-4-boronic acid (3.16 g, 11 mmol), potassium carbonate (2.76 g, 20 mmol), toluene 50 mL Add 10 mL of water and 10 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and then recrystallized with toluene and n-heptane to obtain 2.58 g (52%) of Compound 2-5.

MS (MALDI-TOF) m / z: 496 [M] +

Synthesis Example 2-6

Synthesis of Compound 2-6

9-bromo-10-phenylanthracene (3.33 g, 10 mmol) and dibenzofuran-7-phenyl-4-boronic acid (3.16 g, 11 mmol), potassium carbonate (2.76 g, 20 mmol), toluene 50 mL Add 10 mL of water and 10 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized with toluene and n-heptane to obtain 2.33 g (47%) of Compound 2-6.

MS (MALDI-TOF) m / z: 496 [M] +

Synthesis Example 2-7

Synthesis of Compound 2-37

9-bromo-10-phenylanthracene (3.33 g, 10 mmol) and naphtho [2,3-b] benzofuran-3-yl-boronic acid (2.88 g, 11 mmol), potassium carbonate (2.76 g, 20 mmol), 50 mL of toluene, 10 mL of water, and 10 mL of ethanol are added. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized with toluene to obtain 2.49 g (53%) of compound 2-37.

MS (MALDI-TOF) m / z: 470 [M] +

Synthesis Example 2-8

Synthesis of Compound 2-38

9-bromo-10-phenylanthracene (3.33 g, 10 mmol) and naphtho [1,2-b] benzofuran-9-yl-boronic acid (2.88 g, 11 mmol), potassium carbonate (2.76 g, 20 mmol), 50 mL of toluene, 10 mL of water, and 10 mL of ethanol are added. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized with toluene to obtain 2.49 g (53%) of compound 2-38.

MS (MALDI-TOF) m / z: 470 [M] +

Synthesis Example 2-9

Synthesis of Compound 2-39

9-bromo-10-phenylanthracene (3.33 g, 10 mmol) and 2- (dinaphtho [2,1-b: 1 ', 2'-d] furan-5-yl) -4,4,5, Add 5-tetramethyl-1,3,2-dioxaborolane (4.73 g, 12 mmol), potassium carbonate (2.76 g, 20 mmol), toluene 50 mL, water 10 mL, ethanol 10 mL. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized with toluene to obtain 2.81 g (54%) of compound 2-39.

MS (MALDI-TOF) m / z: 520 [M] +

Synthesis Example 2-10

Synthesis of Compound 2-61

10-bromo-9- (naphthalene-1'-yl) anthracene (3.83 g, 10.0 mmol) and dibenzofuran-4-boronic acid (2.34 g, 11 mmol), potassium carbonate (5.16 g, 20 mmol), Add 100 mL of toluene, 20 mL of water, and 100 mL of ethanol. Tetrakistriphenylphosphine palladium 0.231 g (0.2 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized from toluene to obtain 3.20 g (37%) of compound 2-61.

MS (MALDI-TOF) m / z: 470 [M] +

Synthesis Example 2-11

Synthesis of Compound 2-62

10-bromo-9- (naphthalene-2'-yl) anthracene (3.83 g, 10.0 mmol) and dibenzofuran-4-boronic acid (2.34 g, 11 mmol), potassium carbonate (5.16 g, 20 mmol), Add 100 mL of toluene, 20 mL of water, and 100 mL of ethanol. Tetrakistriphenylphosphine palladium 0.231 g (0.2 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized from toluene to obtain 4.79 g (55%) of compound 2-62.

MS (MALDI-TOF) m / z: 470 [M] +

Synthesis Example 2-12

Synthesis of Compound 2-66

4- (10-bromoanthracene-9-yl) dibenzofuran (4.23 g, 10.0 mmol) and (4- (naphthalen-1-yl) phenyl) boronic acid (2.72 g, 11.0 mmol), potassium carbonate (5.16 g, 20 mmol), 100 mL of toluene, 20 mL of water, and 100 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, water was added, the layer was separated, and the organic layer was treated with MgSO ₄ to remove moisture. After filtration, the filtrate was concentrated under reduced pressure and recrystallized with dichloromethane and n-heptane to give 1.85 g (34%) of compound 2-66.

MS (MALDI-TOF) m / z: 546 [M] +

Synthesis Example 2-13

Synthesis of Compound 2-67

4- (10-bromoanthracene-9-yl) dibenzofuran (4.23 g, 10.0 mmol) and (4- (naphthalen-2-yl) phenyl) boronic acid (2.72 g, 11.0 mmol), potassium carbonate (5.16 g, 20 mmol), 100 mL of toluene, 20 mL of water, and 100 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and then recrystallized from toluene to obtain 3.06 g (56%) of compound 2-67.

MS (MALDI-TOF) m / z: 546 [M] +

Synthesis Example 2-14

Synthesis of Compound 2-73

4- (10-bromoanthracene-9-yl) dibenzofuran (4.23 g, 10.0 mmol) and (4-phenylnaphthalen-1-yl) boronic acid (2.72 g, 11.0 mmol), potassium carbonate (5.16 g, 20 mmol), 100 mL of toluene, 20 mL of water, and 100 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Then, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized from toluene to obtain 2.67 g (49%) of compound 2-73.

MS (MALDI-TOF) m / z: 546 [M] +

Synthesis Example 2-15

Synthesis of Compound 2-75

4- (10-bromoanthracene-9-yl) dibenzofuran (4.23 g, 10.0 mmol) and (6-phenylnaphthalen-2-yl) boronic acid (2.72 g, 11.0 mmol), potassium carbonate (5.16 g, 20 mmol), 100 mL of toluene, 20 mL of water, and 100 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized from toluene to obtain 3.06 g (56%) of compound 2-75.

MS (MALDI-TOF) m / z: 546 [M] +

Synthesis Example 2-16

Synthesis of Compound 2-78

10-bromo-9- (naphthalene-1'-yl) anthracene (3.83 g, 10.0 mmol) and dibenzofuran-3-boronic acid (2.34 g, 11 mmol), potassium carbonate (5.16 g, 20 mmol), Add 100 mL of toluene, 20 mL of water, and 100 mL of ethanol. Tetrakistriphenylphosphine palladium 0.231 g (0.2 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized from toluene to obtain 2.49 g (53%) of compound 2-78.

MS (MALDI-TOF) m / z: 470 [M] +

Synthesis Example 2-17

Synthesis of Compound 2-79

10-bromo-9- (naphthalene-2'-yl) anthracene (3.83 g, 10.0 mmol) and dibenzofuran-3-boronic acid (2.34 g, 11 mmol), potassium carbonate (5.16 g, 20 mmol), Add 100 mL of toluene, 20 mL of water, and 100 mL of ethanol. Tetrakistriphenylphosphine palladium 0.231 g (0.2 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized from toluene to obtain 2.02 g (43%) of compound 2-79.

MS (MALDI-TOF) m / z: 470 [M] +

Synthesis Example 2-18

Synthesis of Compound 2-83

3- (10-bromoanthracene-9-yl) dibenzofuran (4.23 g, 10.0 mmol) and (4- (naphthalen-1-yl) phenyl) boronic acid (2.72 g, 11.0 mmol), potassium carbonate (5.16 g, 20 mmol), 100 mL of toluene, 20 mL of water, and 100 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, water was added, the layer was separated, and the organic layer was treated with MgSO ₄ to remove moisture. After filtration, the filtrate was concentrated under reduced pressure and recrystallized with dichloromethane and n-heptane to give 1.37 g (25%) of compound 2-83.

MS (MALDI-TOF) m / z: 546 [M] +

Synthesis Example 2-19

Synthesis of Compound 2-84

3- (10-bromoanthracene-9-yl) dibenzofuran (4.23 g, 10.0 mmol) and (4- (naphthalen-2-yl) phenyl) boronic acid (2.72 g, 11.0 mmol), potassium carbonate (5.16 g, 20 mmol), 100 mL of toluene, 20 mL of water, and 100 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and then recrystallized from toluene to obtain 3.06 g (56%) of compound 2-84.

MS (MALDI-TOF) m / z: 546 [M] +

Synthesis Example 2-20

Synthesis of Compound 2-90

3- (10-bromoanthracene-9-yl) dibenzofuran (4.23 g, 10.0 mmol) and (4-phenylnaphthalen-1-yl) boronic acid (2.72 g, 11.0 mmol), potassium carbonate (5.16 g, 20 mmol), 100 mL of toluene, 20 mL of water, and 100 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized from toluene to obtain 2.40 g (44%) of compound 2-90.

MS (MALDI-TOF) m / z: 546 [M] +

Synthesis Example 2-21

Synthesis of Compound 2-92

3- (10-bromoanthracene-9-yl) dibenzofuran (4.23 g, 10.0 mmol) and (6-phenylnaphthalen-2-yl) boronic acid (2.72 g, 11.0 mmol), potassium carbonate (5.16 g, 20 mmol), 100 mL of toluene, 20 mL of water, and 100 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized from toluene to obtain 2.30 g (42%) of compound 2-92.

MS (MALDI-TOF) m / z: 546 [M] +

Synthesis Example 2-22

Synthesis of Compound 2-95

10-bromo-9- (naphthalene-1'-yl) anthracene (3.83 g, 10.0 mmol) and dibenzofuran-2-boronic acid (2.34 g, 11 mmol), potassium carbonate (5.16 g, 20 mmol), Add 100 mL of toluene, 20 mL of water, and 100 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.2 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized from toluene to obtain 2.54 g (54%) of compound 2-95.

MS (MALDI-TOF) m / z: 470 [M] +

Synthesis Example 2-23

Synthesis of Compound 2-96

10-bromo-9- (naphthalene-2'-yl) anthracene (3.83 g, 10.0 mmol) and dibenzofuran-2-boronic acid (2.34 g, 11 mmol), potassium carbonate (5.16 g, 20 mmol), Add 100 mL of toluene, 20 mL of water, and 100 mL of ethanol. Tetrakistriphenylphosphine palladium 0.231 g (0.2 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized from toluene to obtain 2.54 g (54%) of compound 2-96.

MS (MALDI-TOF) m / z: 470 [M] +

Synthesis Example 2-24

Synthesis of Compound 2-100

2- (10-bromoanthracene-9-yl) dibenzofuran (4.23 g, 10.0 mmol) and (4- (naphthalen-1-yl) phenyl) boronic acid (2.72 g, 11.0 mmol), potassium carbonate (5.16 g, 20 mmol), 100 mL of toluene, 20 mL of water, and 100 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, water was added, the layer was separated, and the organic layer was treated with MgSO ₄ to remove moisture. After filtration, the filtrate was concentrated under reduced pressure and recrystallized with dichloromethane and n-heptane to give 1.27 g (22%) of compound 2-100.

MS (MALDI-TOF) m / z: 546 [M] +

Synthesis Example 2-25

Synthesis of Compound 2-101

2- (10-bromoanthracene-9-yl) dibenzofuran (4.23 g, 10.0 mmol) and (4- (naphthalen-2-yl) phenyl) boronic acid (2.72 g, 11.0 mmol), potassium carbonate (5.16 g, 20 mmol), 100 mL of toluene, 20 mL of water, and 100 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and then recrystallized from toluene to obtain 3.17 g (55%) of compound 2-101.

MS (MALDI-TOF) m / z: 546 [M] +

Synthesis Example 2-26

Synthesis of Compound 2-142

9-bromo-10- (4- (naphthalen-1-yl) phenyl) anthracene (4.59 g, 10 mmol) and 2- (dinaphtho [2,1-b: 1 ', 2'-d] furan- 5-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolan (4.73 g, 12 mmol), potassium carbonate (2.76 g, 20 mmol), toluene 50 mL, water 10 Add mL and 10 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized with toluene to obtain 3.74 g (58%) of compound 2-142.

MS (MALDI-TOF) m / z: 646 [M] +

Synthesis Example 2-27

Synthesis of Compound 2-191

10-bromo-9- (naphthalene-1'-yl) anthracene (3.83 g, 10.0 mmol) and naphtho [2,3-b] benzofuran-3-yl-boronic acid (2.88 g, 11 mmol), Add potassium carbonate (2.76 g, 20 mmol), toluene 50 mL, water 10 mL, and ethanol 10 mL. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and then recrystallized with toluene to obtain 3.17 g (61%) of compound 2-191.

MS (MALDI-TOF) m / z: 520 [M] +

Synthesis Example 2-28

Synthesis of Compound 2-193

9-([1,1'-biphenyl] -4-yl) -10-bromoanthracene (4.09 g, 10 mmol) and 2- (dinaphtho [2,1-b: 1 ', 2'-d ] Furan-5-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolan (4.73 g, 12 mmol), potassium carbonate (2.76 g, 20 mmol), toluene 50 mL Add 10 mL of water and 10 mL of ethanol. Tetrakistriphenylphosphine palladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. Thereafter, the reaction mixture was cooled to room temperature, and the resulting solid was washed with toluene, methanol, and water, and recrystallized with toluene to obtain 3.28 g (55%) of Compound 2-193.

MS (MALDI-TOF) m / z: 596 [M] +

Comparative Synthesis Example 1

Synthesis of Compound 1-A

Reaction was conducted in the same manner as in Synthesis Example 1-1, except that 3.60 g (10.0 mmol) of 1,6-dibromopyrene and 5.08 g (30 mmol) of Diphenylamine were used, and 3.86 g of Compound 1-A was 72%. Obtained in yield.

MS (MALDI-TOF) m / z: 536 [M] +

Comparative Synthesis Example 2

Synthesis of Compound 1-B

Synthesis except that 3.60 g (10.0 mmol) of 1,6-dibromopyrene and 8.02 g (30 mmol) of 5- (tert-butyl) -N- (2,5-dimethylphenyl) -2-methylaniline were used. Reaction was conducted in the same manner as in Example 1-1 to obtain 4.76 g of Compound 1-B in a yield of 65%.

MS (MALDI-TOF) m / z: 733 [M] +

Comparative Synthesis Example 3

4.16 g (10.0 mmol) of 1,6-dibromo-3,8-diethylpyrene and 8.02 g (30 mmol) of 5- (tert-butyl) -N- (2,5-dimethylphenyl) -2-methylaniline The reaction was performed in the same manner as in Synthesis Example 1-1, except that 4.73 g of Compound 1-C was obtained in a yield of 60%.

MS (MALDI-TOF) m / z: 789 [M] +

Example : film PL  Data measurement

After depositing the following compounds 2-B, 2-C or 2-62 on the ITO thin film as a host, doping 1-B or 1-7 of the present invention 3% to form a light emitting layer, and then measuring PL in the film state Did.

[Compound 2-B] [Compound 2-C]

Comparative example Example Host Compound 2- C Compound 2- B Compound 2-62 Compound 2- C Compound 2- B Compound 2-62 Dopant Compound 1-B Compound 1-B Compound 1-B Compound 1-7 Compound 1-7 Compound 1-7 PL 462 464 466 459 459 459 result PL fluctuation O PL fluctuation X

As a blue host, a compound without a polar group and a compound in which a polar substituent was introduced were used. As a result of measuring the wavelength when the dopant of the present invention was used as a blue dopant, when the dopant of the present invention was used, the compound into which a polar substituent was introduced was used as a host. Even if used, it can be confirmed that there is no change in wavelength.

On the other hand, when a conventional dopant and a polar substituent-introduced compound were used as a host, it was confirmed to move in a long wavelength (red direction).

Example  One: Of organic electroluminescent devices  Produce

The substrate in which the light-reflecting layer Ag alloy and the ITO (10 nm) anode of the organic light emitting device were sequentially stacked was divided into a cathode, an anode region, and an insulating layer through a photo-lithography process to be patterned. Subsequently, for the purpose of increasing the work function of the anode (ITO) and descum, it was surface treated with UV Ozone treatment and O2: N2 plasma. A 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) was formed on the hole injection layer (HIL) to a thickness of 100 mm 2. Then, on the hole injection layer, N4, N4, N4 ', N4'-tetra ([1,1'-biphenyl] -4-yl)-[1,1'-biphenyl] -4,4'- Diamine was vacuum-deposited to form a hole transport layer having a thickness of 1000 mm 2. N-phenyl-N- (4- (spiro [benzo [de] anthracene-7,9'-fluorene] -2'-yl) phenyl) di as an electron blocking layer (EBL) on the hole transport layer (HTL) Forming benzo [b, d] furan-4-amine to a thickness of 150 Å, depositing compound 2-1 as a host of a blue light-emitting layer on the electron blocking layer (EBL), and at the same time, compound 1-1 with dopant 4% The light emitting layer (EML) was formed to a thickness of 200 Pa by doping.

On top of that, 2- (4- (9,10-di (naphthalen-2-yl) anthracene-2-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole and LiQ in a weight ratio of 1: 1 The electron transport layer (ETL) was deposited to a thickness of 360 하여 by mixing, and magnesium (Mg) and silver (Ag) as a cathode were deposited at a thickness of 160 로 at a 9: 1 ratio. In addition, N4, N4'-diphenyl-N4, N4'-bis (4- (9-phenyl-9H-carbazol-3-yl) phenyl)-[1,1 'as a capping layer (CPL) on the cathode. -Biphenyl] -4,4'-diamine was deposited to a thickness of 63-65 nm. An organic electroluminescent device was manufactured by bonding a seal cap with a UV curable adhesive on the capping layer (CPL) to protect the organic electroluminescent device from O2 or moisture in the atmosphere.

Example  2 to 36: Of organic electroluminescent devices  Produce

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound as described in Table 4 below was used instead of Compound 1-1 as a dopant, and the doping amount of the dopant was adjusted. .

Comparative example  1 to 3: Of organic electroluminescent devices  Produce

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 1-A to 1-C were used instead of Compound 1 as a dopant.

Comparative example  4 to 5: Of organic electroluminescent devices  Produce

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following compounds 2-A to 2-B were used instead of Compound 2 as a host.

[Compound 2-A] [Compound 2-B] [Compound 2-C]

Experimental example  One: Of organic electroluminescent devices  Character analysis

Below using the organic electroluminescent device prepared in Examples 1 to 9 and Comparative Example 1 to compare the characteristics at 1000 cd / m2 luminance, the results are shown in Table 2 below.

division DOPANT HOST Volt lm / W Cd / A CIEx CIEy EQE ( % ) Comparative Example 1 1-A 2-B 4.3 4.0 5.2 0.136 0.054 9.4 Comparative Example 2 1-A 2-1 4.0 3.8 4.8 0.136 0.055 8.7 Comparative Example 3 1-B 2-1 4.0 3.7 4.7 0.137 0.052 8.9 Comparative Example 4 1-C 2-1 4.1 3.8 4.9 0.136 0.053 9.2 Comparative Example 5 1-1 2-A 4.3 3.9 5.3 0.137 0.05 10.4 Comparative Example 6 1-1 2-B 4.4 4.0 5.5 0.135 0.052 10.5 Example 1 1-1 2-1 4.1 4.0 5.2 0.136 0.054 9.4 Example 2 1-4 2-1 3.9 4.5 5.6 0.14 0.054 10.3 Example 3 1-5 2-1 3.9 5.4 6.7 0.134 0.056 11.6 Example 4 1-7 2-1 3.9 5.4 6.7 0.128 0.081 9.2 Example 5 1-12 2-1 4.0 4.7 5.9 0.137 0.05 11.6 Example 6 1-13 2-1 4.0 4.3 5.2 0.136 0.054 9.4 Example 7 1-14 2-1 4.0 4.7 5.9 0.138 0.049 11.7 Example 8 1-16 2-1 4.0 4.6 5.9 0.135 0.058 10.5 Example 9 1-76 2-1 4.1 4.0 5.2 0.133 0.058 9.3 Example 10 1-77 2-1 4.0 4.3 5.5 0.135 0.052 10.5 Example 11 1-1 2-2 4.0 4.6 5.9 0.135 0.058 10.5 Example 12 1-7 2-2 3.9 4.8 5.9 0.135 0.058 10.5 Example 13 1-12 2-2 3.9 4.5 5.6 0.14 0.054 10.3 Example 14 1-1 2-39 3.7 5.0 5.9 0.138 0.049 11.7 Example 15 1-7 2-39 3.6 4.5 5.2 0.136 0.054 9.4 Example 16 1-12 2-39 3.7 4.8 5.6 0.14 0.054 10.3 Example 17 1-12 2-37 3.8 4.9 5.9 0.135 0.058 10.5 Example 18 1-12 2-38 3.8 4.3 5.2 0.136 0.054 9.4 Example 19 1-12 2-61 3.9 4.8 5.9 0.138 0.049 11.7 Example 20 1-12 2-62 4.0 4.3 5.5 0.135 0.052 10.5 Example 21 1-12 2-66 4.1 4.0 5.2 0.136 0.054 9.4 Example 22 1-12 2-67 3.9 4.5 5.6 0.14 0.054 10.3 Example 23 1-12 2-75 3.9 4.4 5.5 0.135 0.052 10.5 Example 24 1-12 2-78 3.8 4.6 5.6 0.14 0.054 10.3 Example 25 1-12 2-79 3.9 4.8 5.9 0.138 0.049 11.7 Example 26 1-12 2-83 3.9 4.2 5.2 0.136 0.054 9.4 Example 27 1-12 2-84 4.0 4.3 5.5 0.135 0.052 10.5 Example 28 1-12 2-90 4.0 4.6 5.9 0.135 0.058 10.5 Example 29 1-12 2-92 3.9 4.4 5.5 0.135 0.052 10.5 Example 30 1-12 2-95 3.9 4.8 5.9 0.138 0.049 11.7 Example 31 1-12 2-96 3.9 4.4 5.5 0.135 0.052 10.5 Example 32 1-12 2-100 3.4 4.5 5.2 0.136 0.054 9.4 Example 33 1-12 2-101 3.7 5.7 6.7 0.134 0.056 11.6 Example 34 1-12 2-142 3.6 4.5 5.2 0.136 0.054 9.4 Example 35 1-12 2-191 3.8 4.6 5.6 0.14 0.054 10.3 Example 36 1-12 2-193 3.7 4.7 5.5 0.135 0.052 10.5

Referring to Table 2, in the case of the organic light emitting device according to the present invention, when compared with the comparative example, the driving voltage (Volt) represents equal or less (low driving voltage), and it can be seen that the luminous efficiency (Cd / A) is improved. have.

Claims (13)

A first electrode;
A second electrode; And
An organic electroluminescent device comprising at least one layer of an organic film between the first electrode and the second electrode,
The organic layer includes at least one layer selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer,
The light emitting layer is an organic electroluminescent device comprising a compound represented by the following formula (3) and a compound represented by the following formula (2):
[Formula 3]

here,
R ₁ to R ₈ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, nitro group _, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alke having 2 to 30 carbon atoms A C 2 to C 30 substituted or unsubstituted carbon atom Alkynyl group, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms of An aryl group, substituted or unsubstituted, having 6 to 30 carbon atoms Heteroaryl group, substituted or unsubstituted 6 to 30 carbon atoms A heteroaryl alkyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms,
R ₉ and R ₁₀ are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, a substituted or unsubstituted carbon atom having 1 to 10 carbon atoms, It is selected from the group consisting of an alkoxy group, a halogen, a cyano group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, and an arylsilyl group having 6 to 30 carbon atoms,
R ₉ and R ₁₀ are each independently hydrogen, deuterium, urethane group, carboxyl group, cyano group, nitro group, halogen group, hydroxy group, carboxylate group, alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms , An alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, and one or more substituents selected from the group consisting of a heteroalkyl group having 2 to 30 carbon atoms, and when the substituents are plural, Same or different,
n is an integer from 1 to 3,
[Formula 2]

here,
R ₁₁ to R ₂₀ are the same as or different from each other, and at least one or more is -L ₂ -Ar ₁ and / or -L ₃ -Ar ₂ ,
L ₂ and L ₃ are the same or different from each other, and each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 6 to 30 nuclear atoms, a substituted or unsubstituted carbon number. 2 to 10 alkylene groups, substituted or unsubstituted cycloalkylene groups having 2 to 10 carbon atoms, substituted or unsubstituted alkenylene groups having 2 to 10 carbon atoms, substituted or unsubstituted cycloalkenylene groups having 2 to 10 carbon atoms, substituted or unsubstituted Heteroalkylene group having 2 to 10 carbon atoms, substituted or unsubstituted heterocycloalkylene group having 2 to 10 carbon atoms, substituted or unsubstituted heteroalkenylene group having 2 to 10 carbon atoms and substituted or unsubstituted heterocycloalkenylene having 2 to 10 carbon atoms Is selected from the group consisting of
Ar ₁ and Ar ₂ are the same or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. , A substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, A substituted or unsubstituted cycloalkenyl group having 1 to 20 carbon atoms and a substituted or unsubstituted heteroalkenyl group having 1 to 20 carbon atoms,
R ₁₁ to R ₂₀ other than -L ₂ -Ar ₁ or -L ₃ -Ar ₂ are the same or different from each other, and each independently hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted carbon number 3 to 30 cycloalkyl groups, substituted or unsubstituted alkenyl groups having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 24 carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 30 carbon atoms, substituted or unsubstituted 7 to 7 carbon atoms 30 aralkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and a substituted or unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms,
R ₁ to R _8, L ₂ to L ₃ , Ar ₁ to Ar ₂ and R ₁₁ to R ₂₀ are each independently hydrogen, deuterium, cyano group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted Alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted carbon number Aryl group having 6 to 30, substituted or heteroaryl group having 2 to 30 carbon atoms, substituted or unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted carbon number 1 to 30 alkylamino group, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms are Chelamino group, substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms and substituted or unsubstituted 6 to 30 carbon atoms It may be further substituted with one or more substituents selected from the group consisting of aryloxy groups, and when the number of substituents is plural, they are the same or different from each other. delete According to claim 1,
Any one of the R ₁ to R ₈ is an organic electroluminescent device which is a functional group represented by the following formula (4):
[Formula 4]

[Formula 5]

here,
L is a single bond, a substituted or unsubstituted C ₆ -C ₁₈ arylene group, or a substituted or unsubstituted C ₆ -C ₁₈ heteroarylene group,
M is hydrogen, deuterium, or a functional group represented by Formula 5 above,
Ar ₃ and Ar ₄ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted Alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon having 2 to 24 carbon atoms Alkynyl group, a substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted carbon having 6 to 30 carbon atoms Aryl group, substituted or unsubstituted, having 2 to 30 carbon atoms A heteroaryl group, a substituted or unsubstituted C ₆ -C ₃₀ heteroarylalkyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms and an arylsilyl group having 6 to 30 carbon atoms, or Ar ₃ and Ar ₄ Is connected to each other, may form a ring of 6 to 18 members including one or more N, O or S,
The L, Ar ₃ and Ar ₄ are each independently hydrogen, deuterium, urethane group, carboxy group, cyano group, nitro group, halogen group, hydroxy group, carboxylate group, 1 to 30 carbon atoms alkyl group, 2 to 30 carbon atoms Alkenyl group, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 30 carbon atoms, heteroalkyl group having 2 to 30 carbon atoms, aralkyl group having 7 to 30 carbon atoms, aryl group having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms Group, a heteroaryl alkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, a hetero group having 2 to 24 carbon atoms At least one substituent selected from the group consisting of arylamino groups, alkylsilyl groups having 1 to 30 carbon atoms, arylsilyl groups having 6 to 30 carbon atoms, and aryloxy groups having 6 to 30 carbon atoms. Horizontal may be substituted and, in the case where the substituent is plural, they are the same as or different from each other. According to claim 3,
The Ar ₃ and Ar ₄ is a substituent selected from the group consisting of compounds represented by the following formulas 6 to 11, an organic electroluminescent device:
[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

here,
* Is the part where the bond is made,
p is an integer from 0 to 4,
q is an integer from 0 to 3,
X ₁ is selected from the group consisting of C (R ₂₃ ), N, S and O,
X ₂ , X ₃ , X ₄ and X ₆ are the same as or different from each other, and each independently, are selected from the group consisting of C (R ₂₃ ) (R ₂₄ ), N (R ₂₃ ), S and O,
X ₅ and X ₇ are the same as or different from each other, and each independently C (R ₂₃ ) or N,
R ₂₁ to R ₂₄ are the same or different from each other, and each independently independently independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted 3 to 30 carbon atoms Cycloalkyl group, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon having 2 to 24 carbon atoms Alkynyl group, a substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted carbon having 6 to 30 carbon atoms Aryl group, substituted or unsubstituted, having 2 to 30 carbon atoms A heteroaryl group, a substituted or unsubstituted C ₆ -C ₃₀ heteroarylalkyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms and arylsilyl group having 6 to 30 carbon atoms,
Each of R ₂₁ to R ₂₄ is independently hydrogen, deuterium, urethane group, carboxy group, cyano group, nitro group, halogen group, hydroxy group, carboxylate group, alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms , An alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, Heteroarylalkyl group having 3 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, alkylamino group having 1 to 30 carbon atoms, arylamino group having 6 to 30 carbon atoms, aralkylamino group having 6 to 30 carbon atoms, hetero arylamino group having 2 to 24 carbon atoms , One or more substituents selected from the group consisting of an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms Horizontal may be substituted and, in the case where the substituent is plural, they are the same as or different from each other. According to claim 3,
When M is a functional group represented by Chemical Formula 5, Ar ₃ and Ar ₄ Is an organic electroluminescent device which is a compound represented by any one of the following Chemical Formulas 12 or 13 by forming a ring by being connected to N of M:
[Formula 5]

[Formula 12]

[Formula 13]

here,
X ₈ and X ₉ are the same as or different from each other, and each independently selected from the group consisting of C (R ₂₅ ) (R ₂₆ ), N (R ₂₅ ), C, N, O and S,
R ₂₅ and R ₂₆ are the same or different from each other, and each independently independently independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted 3 to 30 carbon atoms. Cycloalkyl group, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon having 2 to 24 carbon atoms Alkynyl group, a substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted carbon having 6 to 30 carbon atoms Aryl group, substituted or unsubstituted, having 2 to 30 carbon atoms A heteroaryl group, a substituted or unsubstituted C ₆ -C ₃₀ heteroarylalkyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms and arylsilyl group having 6 to 30 carbon atoms, or
Each of R ₂₅ to R ₂₆ is independently hydrogen, deuterium, urethane group, carboxy group, cyano group, nitro group, halogen group, hydroxy group, carboxylate group, alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms , An alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, Heteroarylalkyl group having 3 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, alkylamino group having 1 to 30 carbon atoms, arylamino group having 6 to 30 carbon atoms, aralkylamino group having 6 to 30 carbon atoms, heteroaryl amino group having 2 to 24 carbon atoms , One or more substituents selected from the group consisting of an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms Horizontal may be substituted and, in the case where the substituent is plural, they are the same as or different from each other. According to claim 1,
The compound represented by Formula 2 is an organic electroluminescent device which is a compound represented by Formula 14 below:
[Formula 14]

here,
R ₁₁ to R ₁₈ , Ar ₁ to Ar ₂ and L ₂ to L ₃ are as defined in claim 1. The method of claim 6,
The L ₂ and L ₃ are the same as or different from each other, and each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 6 to 30 nuclear atoms. . The method of claim 6,
At least one of Ar ₁ and Ar ₂ is an organic electroluminescent device which is a compound represented by the following Chemical Formula 15:
[Formula 15]

here,
R ₂₇ to R ₃₄ are the same as or different from each other, and at least one or more -L ₂ -Ar ₁ And / or -L ₃ -Ar ₂ ,
X is O or S,
-L ₂ -Ar ₁ And / or R ₂₇ to R ₃₄ other than -L ₃ -Ar ₂ are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted 2 to 24 carbon atoms Alkynyl group, a substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted carbon having 6 to 30 carbon atoms Aryl group, substituted or unsubstituted, having 2 to 30 carbon atoms Heteroaryl group, a substituted or unsubstituted C ₆ -C ₃₀ heteroarylalkyl group is selected from the group consisting of substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms and arylsilyl group having 6 to 30 carbon atoms, and saturated or unsaturated together with adjacent groups. Condensed rings can be further formed,
The R ₂₇ to R ₃₄ and the saturated or unsaturated condensed ring formed by them are each independently hydrogen, deuterium, urethane group, carboxyl group, cyano group, nitro group, halogen group, hydroxy group, carboxylate group, carbon number 1 to Alkyl group of 30 to 30 carbon atoms, alkenyl group of 2 to 30 carbon atoms, alkynyl group of 2 to 24 carbon atoms, cycloalkyl group of 3 to 30 carbon atoms, heteroalkyl group of 2 to 30 carbon atoms, aralkyl group of 7 to 30 carbon atoms, aryl of 6 to 30 carbon atoms Group, heteroaryl group having 2 to 30 carbon atoms, heteroarylalkyl group having 3 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, alkylamino group having 1 to 30 carbon atoms, arylamino group having 6 to 30 carbon atoms, ar having 6 to 30 carbon atoms Alkylamino group, heteroaryl amino group having 2 to 24 carbon atoms, alkylsilyl group having 1 to 30 carbon atoms, arylsilyl group having 6 to 30 carbon atoms and aryloxy group having 6 to 30 carbon atoms It may be further substituted with one or more substituents selected from the Luru group, and when the substituents are plural, they are the same or different from each other. The organic electroluminescent device according to claim 8, wherein the formula 15 is a compound represented by the following formulas 16 to 24:
[Formula 16]

[Formula 17]

[Formula 18]

[Formula 19]

[Formula 20]

[Formula 21]

[Formula 22]

[Formula 23]

[Formula 24]

here,
X is O or S,
e is an integer from 0 to 6,
f is an integer from 0 to 6,
g is an integer from 0 to 4,
h is an integer from 0 to 4,
R ₃₅ to R ₃₇ are the same as or different from each other, and each independently a single bond, hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted 3 to 30 carbon atoms Cycloalkyl group, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon having 2 to 24 carbon atoms Alkynyl group, a substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted carbon having 6 to 30 carbon atoms Aryl group, substituted or unsubstituted, having 2 to 30 carbon atoms A heteroaryl group, a substituted or unsubstituted C ₆ -C ₃₀ heteroarylalkyl group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms and arylsilyl group having 6 to 30 carbon atoms,
Any one of R ₃₅ to R ₃₇ is combined with L ₂ or L ₃ . The method of claim 6,
R ₁₁ to R ₁₈ are the same or different from each other, and each independently hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and substituted or unsubstituted carbon number 6 to 30 An organic electroluminescent device selected from the group consisting of aryl groups. According to claim 1,
The compound represented by Chemical Formula 3 is an organic electroluminescent device selected from the group consisting of the following compounds:

According to claim 1,
The compound represented by Formula 2 is an organic electroluminescent device selected from the group consisting of the following compounds:

According to claim 1,
The light emitting layer includes a dopant and a host,
The dopant includes a compound represented by Formula 3 below,
The host is an organic electroluminescent device comprising a compound represented by the following formula (2):
[Formula 3]

[Formula 2]

here,
n, R ₁ to R ₂₀ are as defined in claim 1.

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