WO2018128470A1

WO2018128470A1 - Organic electroluminescent element

Info

Publication number: WO2018128470A1
Application number: PCT/KR2018/000274
Authority: WO
Inventors: 이순창; 정재호; 강현빈; 유지웅; 홍상훈
Original assignee: 머티어리얼사이언스 주식회사
Priority date: 2017-01-05
Filing date: 2018-01-05
Publication date: 2018-07-12

Abstract

The present invention relates to an organic electroluminescent element and, more specifically, to an organic electroluminescent element, wherein novel pyrene-based and anthracene-based organic compounds are contained in at least one organic layer included in the organic electroluminescent element.

Description

Organic light emitting diode

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 an anthracene-based organic compound in at least one organic layer included in the organic electroluminescent device.

OLEDs were manufactured in 1987 by Kodak's C.W. Since Tang developed the first organic EL devices (CW Tang, SA Vanslyke, Applied Physics Letters, Vol. 51, p. 913, 1987) using aluminum compounds in aromatic diamines as light emitting layers, multi-layer thin film organic electroluminescence Research on devices and organic materials is being actively conducted. The organic light emitting display device is simpler in structure than other flat panel display devices such as a liquid crystal display (LCD), a plasma display panel (PDP), and a field emission display (FED), has various advantages in the manufacturing process, and has high luminance and viewing angle. Due to its excellent characteristics, fast response speed and low driving voltage, it has been commercialized as a light source such as a back light of a flat panel display such as a wall-mounted TV or a display, an illumination, a billboard.

In general, an organic light emitting display device is a device in which holes and electrons meet and emit light when a voltage is applied to a cathode (electron injection electrode) and an anode (hole injection electrode). It has a structure including an organic layer. In this case, the organic light emitting device may include a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron injection, in addition to the light emitting layer (EML). Electron Injection Layer (EIL) may be included, and may further include an Electron Blocking Layer (EBL) or a Hole Blocking Layer (HBL) as necessary to increase the efficiency of the light emitting layer. have. The organic light emitting 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, a problem arises in that the maximum light emission wavelength is shifted to a long wavelength due to intermolecular interaction, color purity is reduced, or the efficiency of the device is reduced due to the light emission attenuation effect. Therefore, a host / dopant system may be used as the light emitting material to increase the color purity and the light emission efficiency through energy transfer.

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

The light emitting layer is composed of a red host / dopant, a green host / dopant and a blue host / dopant, respectively. The blue light emitting layer is a host and a dopant capable of achieving excellent blue color in terms of lifetime, efficiency and color purity compared to other colors. Development is required.

Recently, it is important to replace the blue host with a polar derivative such as Dibenzofuran in the existing Polyaromatic System. This is because the oxygen molecules contained in Dibenzofuran increase the polarization rate and dipole moment. These characteristics increase the packing of the host molecules in the device to improve the driving voltage and efficiency of the device and increases the life of the device. In spite of these characteristics, however, it is important to find an ideal host / dopant combination because the existing blue dopant is shifted to a longer 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 is shifted to long wavelength (red) when using a compound contained in Dibenzofuran 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 for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the singular forms "a", "an" and "the" may include the plural forms as well, unless the context clearly indicates otherwise. Also, as used herein, "comprise" and / or "comprising" specifies the presence of the mentioned shapes, numbers, steps, actions, members, elements and / or groups of these. It is not intended to exclude the presence or addition of one or more other shapes, numbers, acts, members, 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" refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.

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

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

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

In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form in which the two or more rings are condensed with an aryl group. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

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

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

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

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

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

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

In order to achieve the above object, the first electrode; Second electrode; And at least one organic layer between the first electrode and the second electrode, wherein the organic layer includes an emission 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. Comprising any one or more layers selected from the group consisting of a layer, the light emitting layer provides an organic electroluminescent device comprising a compound represented by the 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 , 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 alken having 2 to 30 carbon atoms Nyl group, substituted or unsubstituted 2 to 30 carbon atoms Alkynyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C2-C30 heteroalkyl groups, substituted or unsubstituted C7-C30 aralkyl groups, substituted or unsubstituted C6-C30 of Aryl groups, substituted or unsubstituted 6 to 30 carbon atoms Heteroaryl group, substituted or unsubstituted 6 to 30 carbon atoms A heteroarylalkyl group, a substituted or unsubstituted C1-C30 alkylsilyl group, a substituted or unsubstituted C6-C30 arylsilyl group, and a substituted or unsubstituted C6-C30 aryloxy group,

[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 as 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 heteroarylene groups, a substituted or unsubstituted carbon number 2-10 alkylene group, substituted or unsubstituted C2-C10 cycloalkylene group, substituted or unsubstituted C2-C10 alkenylene group, substituted or unsubstituted C2-C10 cycloalkenylene group substituted or unsubstituted C2-C10 heteroalkylene group, substituted or unsubstituted C2-C10 heterocycloalkylene group, substituted or unsubstituted C2-C10 heteroalkenylene group, and substituted or unsubstituted C2-C10 heterocycloalkenylene Is selected from the group consisting of groups,

Ar ₁ and Ar ₂ are the same as 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 , Substituted or unsubstituted C1-C20 cycloalkyl group, substituted or unsubstituted C1-C20 heteroalkyl group, substituted or unsubstituted C1-C20 heterocycloalkyl group, substituted or unsubstituted C1-C20 alkenyl group, 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 as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms , Substituted or unsubstituted C2-C24 alkynyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C2-C30 heteroalkyl group, substituted or unsubstituted C7-C30 aralkyl group, 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 A C2-C24 alkynyl group of a ring, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heteroalkyl group, a substituted or unsubstituted C7-C30 aralkyl group, a substituted or unsubstituted carbon number 6 to 30 aryl groups, substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroarylalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted carbon atoms 1 to 30 30 alkylamino group, substituted or unsubstituted C6-C30 arylamino group, substituted or unsubstituted C6-C30 ar A substituted or unsubstituted hetero arylamino group having 2 to 24 carbon atoms, 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 carbon group having 6 to 30 carbon atoms It may be further substituted with one or more substituents selected from the group consisting of an aryloxy group, when the substituents are a plurality, they are the same or different from each other.

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

[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 group having 1 to 10 carbon atoms 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, 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 , May be further substituted with one or more substituents selected from the group consisting of an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms and a heteroalkyl group having 2 to 30 carbon atoms, and when the substituents are plural, Same or different,

n is an integer of 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 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 the formula (5),

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 groups having 2 to 30 carbon atoms, substituted or unsubstituted 2 to 24 carbon atoms Alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted 6 to 30 carbon atoms Aryl group, substituted or unsubstituted C 2 -C 30 Heteroaryl group, substituted or unsubstituted C ₆ -C ₃₀ heteroarylalkyl group substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and arylsilyl group having 6 to 30 carbon atoms, or Ar ₃ and Ar ₄ May be connected to each other to form a 6 to 18 membered ring containing one or more N, O or S,

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, alkyl group of 1 to 30 carbon atoms, of 2 to 30 carbon atoms Alkenyl groups, alkynyl groups of 2 to 24 carbon atoms, cycloalkyl groups of 3 to 30 carbon atoms, heteroalkyl groups of 2 to 30 carbon atoms, aralkyl groups of 7 to 30 carbon atoms, aryl groups of 6 to 30 carbon atoms, heteroaryl of 2 to 30 carbon atoms Group, C3-C30 heteroarylalkyl group, C1-C30 alkoxy group, C1-C30 alkylamino group, C6-C30 arylamino group, C6-C30 aralkylamino group, C2-C24 hetero At least one substituent selected from the group consisting of an arylamino group, 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, Ar ₃ and Ar ₄ of 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 combination

p is an integer from 0 to 4,

q is an integer of 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 are each independently 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 as 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 C 3 to 30 Of cycloalkyl group, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 2 to 24 carbon atoms Alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted 6 to 30 carbon atoms Aryl group, substituted or unsubstituted C 2 -C 30 Heteroaryl group, substituted or unsubstituted C ₆ -C ₃₀ heteroarylalkyl group substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and arylsilyl group having 6 to 30 carbon atoms,

R ₁₉ to R ₂₁ are each 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 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 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, heteroarylaryl group having 2 to 24 carbon atoms At least one substituent 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 Formula 5, Ar ₃ and Ar ₄ Is connected to N of M to form a ring, and represents a compound represented by any one of the following formula (12) or (13).

[Formula 5]

[Formula 12]

[Formula 13]

here,

X ₈ and X ₉ are the same as or different from each other, and are 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 as 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 C 3 to 30 Of cycloalkyl group, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 2 to 24 carbon atoms Alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted 6 to 30 carbon atoms Aryl group, substituted or unsubstituted C 2 -C 30 Heteroaryl group, substituted or unsubstituted C ₆ -C ₃₀ heteroarylalkyl group substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms and arylsilyl group having 6 to 30 carbon atoms, or

R ₂₅ to R ₂₆ are each 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 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 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, heteroarylaryl group having 2 to 24 carbon atoms At least one substituent 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 Chemical Formula 2 represents a compound represented by the following Chemical Formula 14.

[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 of Formula 14 are the same as or different from each other, each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted nuclear atom 6 Organic electroluminescent device which is from 30 to 30 heteroarylene groups.

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

[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 as 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, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon group having 2 to 24 carbon atoms Alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted 6 to 30 carbon atoms Aryl group, substituted or unsubstituted C 2 -C 30 Heteroaryl group, substituted or unsubstituted C ₆ -C ₃₀ heteroarylalkyl group Substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms and arylsilyl group having 6 to 30 carbon atoms, selected from the group consisting of saturated or unsaturated with adjacent groups Can form additional condensed rings,

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 An alkyl group of 30 to 30 carbon atoms, an alkenyl group of 2 to 30 carbon atoms, an alkynyl group of 2 to 24 carbon atoms, a cycloalkyl group of 3 to 30 carbon atoms, a heteroalkyl group of 2 to 30 carbon atoms, an aralkyl group of 7 to 30 carbon atoms, and an alkyl group of 6 to 30 carbon atoms Aryl group, heteroaryl group of 2 to 30 carbon atoms, heteroarylalkyl group of 3 to 30 carbon atoms, alkoxy group of 1 to 30 carbon atoms, alkylamino group of 1 to 30 carbon atoms, arylamino group of 6 to 30 carbon atoms, of 6 to 30 carbon atoms An aralkylamino group, a heteroarylaryl group having 2 to 24 carbon atoms, 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 It may be further substituted with one or more substituents selected from the group consisting of, when the substituents are plural, they are the same or different from each other.

In one embodiment of the present invention, Chemical Formula 15 represents a compound represented by the following Chemical 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 of 0 to 6,

g is an integer of 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, a halogen, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number 3 to 30 Of cycloalkyl group, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 2 to 24 carbon atoms Alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted 6 to 30 carbon atoms Aryl group, substituted or unsubstituted C 2 -C 30 Heteroaryl group, substituted or unsubstituted C ₆ -C ₃₀ heteroarylalkyl group substituted or unsubstituted alkyl 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, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cyclo having 3 to 30 carbon atoms Alkyl group and substituted or unsubstituted C6-C30 It is selected from the group consisting of an aryl group.

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

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

According to one embodiment of the invention, the light emitting layer of the organic light emitting device of the present invention comprises a dopant and a host, the dopant comprises a compound represented by the formula (1), the host is a compound represented by the formula (2) It may include.

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

The organic compound represented by the general formula (1) of the present invention prevents excited dimer formation of the dopant by introducing an alkyl group of a cyclic compound inside the pyrene molecular core and increases the electron density of the core and the stability of the dopant. Increases its efficiency and lifespan.

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

One embodiment of the present invention provides a material for forming an emission layer comprising an organic compound represented by Formula 1 and an organic compound represented by Formula 2. The light emitting layer forming material may include a conventionally 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 Formula 2, but is not limited thereto.

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

In one embodiment of the present invention, the organic light emitting device of the present invention is a cathode (hole injection electrode), a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML) and a cathode (electron injection electrode) in sequence It may have a stacked structure, and preferably, may further include an electron blocking layer (EBL) between the anode and the light emitting layer, and an electron transport layer (ETL) and an electron injection layer (EIL) between the cathode and the light emitting 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 by way of example. However, the contents exemplified below do not limit the organic light emitting device of the present invention.

Another embodiment of the present invention provides a method of manufacturing an organic light emitting display device according to the present invention, but the contents exemplified below do not limit the method of manufacturing the organic light emitting display device of the present invention.

Specifically, first, a positive electrode is coated on a surface of a substrate by a conventional method to form a positive electrode. At this time, the substrate used is preferably a glass substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling and waterproof. In addition, as the positive electrode material, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, may be used.

Next, a hole injection layer is formed on the surface of the anode by vacuum thermal evaporation or spin coating of a hole injection layer (HIL) material in a conventional manner. Such hole injection layer materials 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 is formed on the surface of the hole injection layer by vacuum thermal evaporation or spin coating of a hole transport layer (HTL) material in a conventional manner. In this case, 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).

The light emitting layer (EML) material on the surface of the hole transport layer by vacuum thermal evaporation or spin coating in a conventional manner to form a light emitting layer. In this case, the compound represented by Chemical Formula 2 may be preferably used as a single light emitting material or a light emitting host material among the light emitting layer materials used, but in the case of green, tris (8-hydroxyquinolinolato) aluminum (Alq ₃ ), Blue, Balq (8-hydroxyquinolineberyllium salt), DPVBi (4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl) series, Spiro ) Material, 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 complex, metal complex of imidazole, thiazole and oxazole and the like can be used.

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

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

An electron transport layer is formed on the surface of the light emitting layer by vacuum thermal evaporation or spin coating of an electron transport layer (ETL) material in a conventional manner. In this case, the electron transport layer material used is not particularly limited, and preferably tris (8-hydroxyquinolinolato) aluminum (Alq ₃ ) may be used.

Alternatively, by forming an additional 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 the triplet exciton or hole from diffusing 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 is preferably (8-hydroxyquinolinola). Earth) lithium (Liq), bis (8-hydroxy-2-methylquinolinolato) -aluminum biphenoxide (BAlq), bathocuproine (BCP), LiF and the like can be used.

An electron injection layer is formed on the surface of the electron transport layer by vacuum thermal evaporation or spin coating of an electron injection layer (EIL) material in a conventional manner. In this case, a material such as LiF, Liq, Li ₂ O, BaO, NaCl, CsF may be used as the electron injection layer material.

The negative electrode material is formed on the surface of the electron injection layer by vacuum thermal deposition 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 the front emission organic light emitting diode, indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode through which light can pass.

The capping layer CPL may be formed on the surface of the cathode by the composition for capping layer formation of the present invention.

According to the present invention, there is provided 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 the efficiency and life of the device.

In addition, according to the present invention, an organic compound including an organic compound capable of easily realizing a device even in a solution process rather than a deposition process that has to be accompanied by the conventional OLED process and solves the process productivity and cost problems of the existing blue dopant material An electroluminescent element is provided.

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

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

A first electrode;

Second electrode; And

An organic electroluminescent device comprising at least one 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 (1) and a compound represented by the following formula (2):

[Formula 1]

here,

[Formula 2]

here,

-L ₂ -Ar ₁ Or R ₁₁ to R ₂₀ other than -L ₃ -Ar ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a 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 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 cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted An alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted carbon number 6 to 30 aryl groups, substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroarylalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted carbon atoms 1 to 30 30 alkylamino group, substituted or unsubstituted C6-C30 arylamino group, substituted or unsubstituted C6-C30 ar A substituted or unsubstituted hetero arylamino group having 2 to 24 carbon atoms, 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 carbon group having 6 to 30 carbon atoms It may be further substituted with one or more substituents selected from the group consisting of an aryloxy group, when the substituents are a plurality, they are the same or different from each other.

The embodiments of the present invention are provided to more fully explain the present invention to those skilled in the art, and the following examples can be modified in various other forms, and the scope of the present invention is It is not limited to an Example. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the inventive concept to those skilled in the art.

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

Synthesis Example

Synthesis of Intermediate 1-A

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

Synthesis Example 1-1

Synthesis of Compound 1-1

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

4.70 g (10.0 mmol) of 1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene and N- (5- (tert-butyl) -2-methylphenyl) -2,4-dimethylaniline 1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd instead of 8.02 g (30 mmol) ] 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 in 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- 5.05 g of 'Compound 1-3' was obtained in a yield of 62% by the same method as in Synthesis Example 1-1, except that 8.02 g (30 mmol) of methylphenyl) -2,4-dimethylaniline was used.

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

Synthesis Example 1-4

Synthesis of Compound 1-4

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

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 6.35 g of 'Compound 1-5' was obtained in a yield of 75% by the same method as the Synthesis Example 1-1, except that 8.08 g (30 mmol) of-(methyltrimethylsilyl) phenyl) aniline was used.

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 4.42 g (10.0 mmol) and 5- (tert-butyl) -N- 5.30 g of 'Compound 1-6' was obtained in a yield of 65% by the same method as in Synthesis Example 1-1, except that 8.02 g (30 mmol) of (2,5-dimethylphenyl) -2-methylaniline was used. .

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

Synthesis Example 1-7

Synthesis of Compound 1-7

4.70 g (10.0 mmol) of 1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene and 4- (tert-butyl) -2, 4.64 g of 'Compound 1-7' was obtained in a yield of 57% except that 7.60 g (30 mmol) of 6-dimethyl-N-phenylaniline was used in the same manner as in Synthesis Example 1-1.

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

Synthesis Example 1-8

Synthesis of Compound 1-8

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

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

Synthesis Example 1-9

Synthesis of Compound 1-9

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

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

Synthesis Example 1-10

Synthesis of Compound 1-10

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

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

Synthesis Example 1-11

Synthesis of Compound 1-11

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

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

Synthesis Example 1-12

Synthesis of Compound 1-12

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

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 was reacted in the same manner as in Synthesis Example 1-1 except that 9.46 g (30 mmol) of 5.09 g of Compound 1-13 was obtained. Obtained in% yield.

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

Synthesis Example 1-14

Synthesis of Compound 1-14

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

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

Synthesis Example 1-15

Synthesis of Compound 1-15

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

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

Synthesis Example 1-16

Synthesis of Compound 1-16

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

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

Synthesis Example 1-17

Synthesis of Compound 1-17

Using 4.70 g (10.0 mmol) of 1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene and 5.08 g (30 mmol) of diphenylamine The reaction was carried out 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

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

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

Synthesis Example 1-19

Synthesis of Compound 1-19

4.70 g (10.0 mmol) of 1,7-dibromo-9-isopropyl-5,5-dimethyl-4,5-dihydro-3H-benzo [cd] pyrene and di ([1,1'-biphenyl ] -5. 5) amine 5.64 g (30 mmol) was used in the same manner as in Synthesis Example 1-1 to give 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

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'-ratio) 3.14 g of 'Compound 1-20' was obtained in a yield of 42% by the same method as in Synthesis Example 1-1, except that 8.85 g (30 mmol) of phenyl] -4-yl) naphthalene-1-amine was used.

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 5.50 g of 'Compound 1-21' was obtained in a yield of 64% except that 8.26 g (30 mmol) of 4-amine was used and reacted in the same manner as in Synthesis Example 1-1.

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

Synthesis Example 1-22

Compound 1-22 Synthesis of

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

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

Synthesis Example 1-23

Synthesis of Compound 1-23

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

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

Synthesis Example 1-24

Synthesis of Compound 1-24

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

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 4.70 g (10.0 mmol) and bis (4-methoxyphenyl) amine 6.88 5.45 g of 'Compound 1-25' was obtained in a yield of 71% except that g (30 mmol) was used in the same manner as in Synthesis Example 1-1.

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

Synthesis Example 1-26

Synthesis of Compound 1-76

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-phenylamine 4.85 g of 'Compound 1-76' was obtained in a yield of 71% except that 5.91 g (30 mmol) was used in the same manner as in Synthesis Example 1-1.

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 4.67 g of 'Compound 1-77' was obtained in a yield of 64% except that 5.91 g (30 mmol) of -tolyl) amine was used in the same manner as in Synthesis Example 1-1.

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) with dibenzofuran-4-boronic acid (2.33 g, 11 mmol), potassium carbonate (2.76 g, 20 mmol), 50 mL of toluene, 10 mL water Add 10 mL of ethanol. Tetrakistriphenylphosphinepalladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. After cooling the reaction mixture to room temperature, the resulting solid was washed with toluene, methanol, water and recrystallized from toluene to give 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) with dibenzofuran-3-boronic acid (2.33 g, 11 mmol), potassium carbonate (2.76 g, 20 mmol), 50 mL of toluene, 10 mL water Add 10 mL of ethanol. Tetrakistriphenylphosphinepalladium (0.231 g, 0.20 mmol) is 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 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) with dibenzofuran-2-boronic acid (2.33 g, 11 mmol), potassium carbonate (2.76 g, 20 mmol), 50 mL of toluene, 10 mL water Add 10 mL of ethanol. Tetrakistriphenylphosphinepalladium (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) with dibenzofuran-1-boronic acid (2.33 g, 11 mmol) potassium carbonate (2.76 g, 20 mmol), 50 mL of toluene, 10 mL water, Add 10 mL of ethanol. Tetrakistriphenylphosphinepalladium (0.231 g, 0.20 mmol) is 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 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) with dibenzofuran-6-phenyl-4-boronic acid (3.16 g, 11 mmol), potassium carbonate (2.76 g, 20 mmol), 50 mL toluene Add 10 mL of water and 10 mL of ethanol. Tetrakistriphenylphosphinepalladium (0.231 g, 0.20 mmol) is 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) with dibenzofuran-7-phenyl-4-boronic acid (3.16 g, 11 mmol), potassium carbonate (2.76 g, 20 mmol), 50 mL toluene Add 10 mL of water and 10 mL of ethanol. Tetrakistriphenylphosphinepalladium (0.231 g, 0.20 mmol) is added and refluxed for 10 hours. The reaction mixture was then cooled to room temperature, and the resulting solid was washed with toluene, methanol and water and recrystallized with toluene and n-heptane to give 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) with naphtho [2,3-b] benzofuran-3-yl-boronic acid (2.88 g, 11 mmol), potassium carbonate (2.76 g, 20 mmol), 50 mL toluene, 10 mL water and 10 mL ethanol. Tetrakistriphenylphosphinepalladium (0.231 g, 0.20 mmol) is added and refluxed for 10 hours. After cooling the reaction mixture to room temperature, the resulting solid was washed with toluene, methanol, water and recrystallized with toluene to give 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) with naphtho [1,2-b] benzofuran-9-yl-boronic acid (2.88 g, 11 mmol), potassium carbonate (2.76 g, 20 mmol), 50 mL toluene, 10 mL water and 10 mL ethanol. Tetrakistriphenylphosphinepalladium (0.231 g, 0.20 mmol) is added and refluxed for 10 hours. After cooling the reaction mixture to room temperature, the resulting solid was washed with toluene, methanol, water and recrystallized with toluene to give 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), 50 mL of toluene, 10 mL water, and 10 mL ethanol. Tetrakistriphenylphosphinepalladium (0.231 g, 0.20 mmol) is added and refluxed for 10 hours. After cooling the reaction mixture to room temperature, the resulting solid was washed with toluene, methanol, water and recrystallized with toluene to give 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) with 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. 0.231 g (0.2 mmol) of tetrakistriphenylphosphinepalladium was added and refluxed for 10 hours. After cooling the reaction mixture to room temperature, the resulting solid was washed with toluene, methanol, water and recrystallized from toluene to give 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) with 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. Tetrakistriphenylphosphinepalladium 0.231 g (0.2 mmol) was added and refluxed for 10 hours. After cooling the reaction mixture to room temperature, the resulting solid was washed with toluene, methanol, water and recrystallized from toluene to give 4.79 g (55%) of the 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. Tetrakistriphenylphosphinepalladium (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 thereto, and the layers were 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. Tetrakistriphenylphosphinepalladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. After cooling the reaction mixture to room temperature, the resulting solid was washed with toluene, methanol, water and recrystallized from toluene to give 3.06 g (56%) of the 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. Tetrakistriphenylphosphinepalladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. After cooling the reaction mixture to room temperature, the resulting solid was washed with toluene, methanol, water and recrystallized from toluene to give 2.67 g (49%) of the 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. Tetrakistriphenylphosphinepalladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. After cooling the reaction mixture to room temperature, the resulting solid was washed with toluene, methanol, water and recrystallized from toluene to give 3.06 g (56%) of the compound 2-75.

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

Synthesis Example 2-16

Synthesis of Compound 2-78

10-bromo-9- (naphthalen-1'-yl) anthracene (3.83 g, 10.0 mmol) with 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. 0.231 g (0.2 mmol) of tetrakistriphenylphosphinepalladium was added and refluxed for 10 hours. The reaction mixture was then cooled to room temperature, and the resulting solid was washed with toluene, methanol and water and recrystallized from toluene to give 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) with 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. 0.231 g (0.2 mmol) of tetrakistriphenylphosphinepalladium was added and refluxed for 10 hours. After cooling the reaction mixture to room temperature, the resulting solid was washed with toluene, methanol, water and recrystallized from toluene to give 2.02 g (43%) of the 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. Tetrakistriphenylphosphinepalladium (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 thereto, and the layers were 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. Tetrakistriphenylphosphinepalladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. The reaction mixture was then 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 2-84.

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. Tetrakistriphenylphosphinepalladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. After cooling the reaction mixture to room temperature, the resulting solid was washed with toluene, methanol, water and recrystallized from toluene to give 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. Tetrakistriphenylphosphinepalladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. After cooling the reaction mixture to room temperature, the resulting solid was washed with toluene, methanol, water and recrystallized from toluene to give 2.30 g (42%) of the 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) with 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. Tetrakistriphenylphosphinepalladium (0.231 g, 0.2 mmol) was added and refluxed for 10 hours. After cooling the reaction mixture to room temperature, the resulting solid was washed with toluene, methanol, water and recrystallized from toluene to give 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) with 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. 0.231 g (0.2 mmol) of tetrakistriphenylphosphinepalladium was added and refluxed for 10 hours. The reaction mixture was then cooled to room temperature, and the resulting solid was washed with toluene, methanol and water and recrystallized from toluene to give 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. Tetrakistriphenylphosphinepalladium (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 thereto, and the layers were 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. Tetrakistriphenylphosphinepalladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. After cooling the reaction mixture to room temperature, the resulting solid was washed with toluene, methanol, water and recrystallized from toluene to give 3.17 g (55%) of the 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-dioxaborolane (4.73 g, 12 mmol), potassium carbonate (2.76 g, 20 mmol), 50 mL toluene, water 10 Add 10 mL of ethanol and mL. Tetrakistriphenylphosphinepalladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. After cooling the reaction mixture to room temperature, the resulting solid was washed with toluene, methanol, water and recrystallized with toluene to give 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- (naphthalen-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), 50 mL of toluene, 10 mL water, and 10 mL ethanol. Tetrakistriphenylphosphinepalladium (0.231 g, 0.20 mmol) is added and refluxed for 10 hours. After cooling the reaction mixture to room temperature, the resulting solid was washed with toluene, methanol, water and recrystallized with toluene to give 3.17 g (61%) of the 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-dioxaborolane (4.73 g, 12 mmol), potassium carbonate (2.76 g, 20 mmol), 50 mL toluene Add 10 mL of water and 10 mL of ethanol. Tetrakistriphenylphosphinepalladium (0.231 g, 0.20 mmol) was added and refluxed for 10 hours. After cooling the reaction mixture to room temperature, the resulting solid was washed with toluene, methanol, water and recrystallized with toluene to give 3.28 g (55%) of compound 2-193.

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

Comparative Synthesis Example 1

Synthesis of Compound 1-A

Except for using 1.60 g (10.0 mmol) of 1,6-dibromopyrene and 5.08 g (30 mmol) of diphenylamine, the reaction was carried out in the same manner as in Synthesis Example 1-1 to give 3.86 g of Compound 1-A in 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 In the same manner as in Example 1-1, 4.76 g of Compound 1-B was obtained 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 carried out in the same manner as in Synthesis Example 1-1 except for using 4.73 g of Compound 1-C in a yield of 60%.

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

실시예: 필름 PL 데이터 측정Example: Film PL Data Measurement

After depositing 3% of 1-B or 1-7 of the present invention by depositing the following compound 2-B, 2-C or 2-62 on the ITO thin film as a host, a light emitting layer was formed, and then PL was measured in a film state. It was.

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

	비교예 Comparative example			실시예Example
호스트Host	화합물 compound 2-2- CC	화합물 compound 2-2- BB	화합물 2-62Compound 2-62	화합물 compound 2-2- CC	화합물 compound 2-2- BB	화합물 2-62Compound 2-62
도펀트Dopant	화합물 1-BCompound 1-B	화합물 1-BCompound 1-B	화합물 1-BCompound 1-B	화합물 1-7Compound 1-7	화합물 1-7Compound 1-7	화합물 1-7Compound 1-7
PLPL	462462	464464	466466	459459	459459	459459
결과result	PL 변동 OPL fluctuation O			PL 변동 XPL fluctuation X

As a blue host, a compound having no polar group and a compound having a polar substituent were used, and the wavelength when the dopant of the present invention was used as a blue dopant was measured. It can be confirmed that there is no change in wavelength even if used.

On the other hand, it was confirmed that when a compound having a conventional dopant and a polar substituent introduced therein was used as a host, it shifted to a long wavelength (red direction).

실시예 1: 유기전계발광소자의 제조Example 1 Fabrication of Organic Electroluminescent Device

The substrate in which the Ag alloy, which is a light-reflective layer, and ITO (10 nm), which is an anode of the organic light emitting device, were sequentially stacked was patterned by dividing the substrate into a cathode, an anode region, and an insulating layer through a photo-lithograph process. Afterwards, UV Ozone treatment and O2: N2 plasma were used for the purpose of increasing the work-function and descum of the anode (ITO). 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) was formed on the hole injection layer (HIL) to a thickness of 100 mm 3. Subsequently, 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 3. 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) Form benzo [b, d] furan-4-amine to a thickness of 150 ,, and deposit Compound 2-1 to the host of the blue light emitting layer on the electron blocking layer (EBL) while simultaneously doping 4% of compound 1-1 with a dopant. Doped to form a light emitting layer (EML) to a thickness of 200 kHz.

On top of that 2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole and LiQ in a weight ratio of 1: 1 Electron transport layer (ETL) was deposited to a thickness of 360 Å by mixing, and magnesium (Mg) and silver (Ag) were deposited to a thickness of 160 로 at a ratio of 9: 1 as the cathode. Further, 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. The organic electroluminescent device was manufactured by bonding a seal cap with a UV curable adhesive on a capping layer (CPL) to protect the organic light emitting device from O 2 or moisture in the air.

실시예 2 내지 36: 유기전계발광소자의 제조Examples 2 to 36: Fabrication of organic electroluminescent device

An organic light emitting diode device was manufactured according to the same method as Example 1 except for using the compound as described in Table 4 below instead of the compound 1-1 as a dopant, and adjusting the doping amount of the dopant. .

비교예Comparative example 1 내지 3: 1 to 3: 유기전계발광소자의Of organic light emitting device 제조 Produce

An organic light emitting diode device was manufactured according to the same method as Example 1 except for using the compound 1-A to 1-C instead of the compound 1 as a dopant.

비교예 4 내지 5 : 유기전계발광소자의 제조Comparative Examples 4 to 5: Preparation of an organic light emitting display device

An organic light emitting diode was manufactured according to the same method as Example 1 except for using the following Compound 2-A to Compound 2-B as a host.

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

실험예 1: 유기전계발광소자의 특성 분석Experimental Example 1: Characterization of the organic light emitting device

Hereinafter, the characteristics were compared at 1000 cd / m 2 luminance using the organic light emitting diodes manufactured in Examples 1 to 9 and Comparative Example 1, and the results are shown in Table 2 below.

구분division	DOPANTDOPANT	HOSTHOST	VoltVolt	lm/Wlm / W	Cd/ACd / A	CIExCIEx	CIEyCIEy	EQE (%)EQE (%)
비교예1Comparative Example 1	1-A1-A	2-B2-B	4.34.3	4.04.0	5.25.2	0.1360.136	0.0540.054	9.49.4
비교예 2Comparative Example 2	1-A1-A	2-12-1	4.04.0	3.83.8	4.84.8	0.1360.136	0.0550.055	8.78.7
비교예3Comparative Example 3	1-B1-B	2-12-1	4.04.0	3.73.7	4.74.7	0.1370.137	0.0520.052	8.98.9
비교예4Comparative Example 4	1-C1-C	2-12-1	4.14.1	3.83.8	4.94.9	0.1360.136	0.0530.053	9.29.2
비교예 5Comparative Example 5	1-11-1	2-A2-A	4.34.3	3.93.9	5.35.3	0.1370.137	0.050.05	10.410.4
비교예 6Comparative Example 6	1-11-1	2-B2-B	4.44.4	4.04.0	5.55.5	0.1350.135	0.0520.052	10.510.5
실시예1Example 1	1-11-1	2-12-1	4.14.1	4.04.0	5.25.2	0.1360.136	0.0540.054	9.49.4
실시예2Example 2	1-41-4	2-12-1	3.93.9	4.54.5	5.65.6	0.140.14	0.0540.054	10.310.3
실시예3Example 3	1-51-5	2-12-1	3.93.9	5.45.4	6.76.7	0.1340.134	0.0560.056	11.611.6
실시예4Example 4	1-71-7	2-12-1	3.93.9	5.45.4	6.76.7	0.1280.128	0.0810.081	9.29.2
실시예5Example 5	1-121-12	2-12-1	4.04.0	4.74.7	5.95.9	0.1370.137	0.050.05	11.611.6
실시예6Example 6	1-131-13	2-12-1	4.04.0	4.34.3	5.25.2	0.1360.136	0.0540.054	9.49.4
실시예7Example 7	1-141-14	2-12-1	4.04.0	4.74.7	5.95.9	0.1380.138	0.0490.049	11.711.7
실시예8Example 8	1-161-16	2-12-1	4.04.0	4.64.6	5.95.9	0.1350.135	0.0580.058	10.510.5
실시예9Example 9	1-761-76	2-12-1	4.14.1	4.04.0	5.25.2	0.1330.133	0.0580.058	9.39.3
실시예 10Example 10	1-771-77	2-12-1	4.04.0	4.34.3	5.55.5	0.1350.135	0.0520.052	10.510.5
실시예11Example 11	1-11-1	2-22-2	4.04.0	4.64.6	5.95.9	0.1350.135	0.0580.058	10.510.5
실시예 12Example 12	1-71-7	2-22-2	3.93.9	4.84.8	5.95.9	0.1350.135	0.0580.058	10.510.5
실시예 13Example 13	1-121-12	2-22-2	3.93.9	4.54.5	5.65.6	0.140.14	0.0540.054	10.310.3
실시예 14Example 14	1-11-1	2-392-39	3.73.7	5.05.0	5.95.9	0.1380.138	0.0490.049	11.711.7
실시예 15Example 15	1-71-7	2-392-39	3.63.6	4.54.5	5.25.2	0.1360.136	0.0540.054	9.49.4
실시예 16Example 16	1-121-12	2-392-39	3.73.7	4.84.8	5.65.6	0.140.14	0.0540.054	10.310.3
실시예 17Example 17	1-121-12	2-372-37	3.83.8	4.94.9	5.95.9	0.1350.135	0.0580.058	10.510.5
실시예 18Example 18	1-121-12	2-382-38	3.83.8	4.34.3	5.25.2	0.1360.136	0.0540.054	9.49.4
실시예 19Example 19	1-121-12	2-612-61	3.93.9	4.84.8	5.95.9	0.1380.138	0.0490.049	11.711.7
실시예 20Example 20	1-121-12	2-622-62	4.04.0	4.34.3	5.55.5	0.1350.135	0.0520.052	10.510.5
실시예 21Example 21	1-121-12	2-662-66	4.14.1	4.04.0	5.25.2	0.1360.136	0.0540.054	9.49.4
실시예 22Example 22	1-121-12	2-672-67	3.93.9	4.54.5	5.65.6	0.140.14	0.0540.054	10.310.3
실시예 23Example 23	1-121-12	2-752-75	3.93.9	4.44.4	5.55.5	0.1350.135	0.0520.052	10.510.5
실시예 24Example 24	1-121-12	2-782-78	3.83.8	4.64.6	5.65.6	0.140.14	0.0540.054	10.310.3
실시예25Example 25	1-121-12	2-792-79	3.93.9	4.84.8	5.95.9	0.1380.138	0.0490.049	11.711.7
실시예 26Example 26	1-121-12	2-832-83	3.93.9	4.24.2	5.25.2	0.1360.136	0.0540.054	9.49.4
실시예 27Example 27	1-121-12	2-842-84	4.04.0	4.34.3	5.55.5	0.1350.135	0.0520.052	10.510.5
실시예 28Example 28	1-121-12	2-902-90	4.04.0	4.64.6	5.95.9	0.1350.135	0.0580.058	10.510.5
실시예 29Example 29	1-121-12	2-922-92	3.93.9	4.44.4	5.55.5	0.1350.135	0.0520.052	10.510.5
실시예 30Example 30	1-121-12	2-952-95	3.93.9	4.84.8	5.95.9	0.1380.138	0.0490.049	11.711.7
실시예 31Example 31	1-121-12	2-962-96	3.93.9	4.44.4	5.55.5	0.1350.135	0.0520.052	10.510.5
실시예 32Example 32	1-121-12	2-1002-100	3.43.4	4.54.5	5.25.2	0.1360.136	0.0540.054	9.49.4
실시예 33Example 33	1-121-12	2-1012-101	3.73.7	5.75.7	6.76.7	0.1340.134	0.0560.056	11.611.6
실시예 34Example 34	1-121-12	2-1422-142	3.63.6	4.54.5	5.25.2	0.1360.136	0.0540.054	9.49.4
실시예 35Example 35	1-121-12	2-1912-191	3.83.8	4.64.6	5.65.6	0.140.14	0.0540.054	10.310.3
실시예 36Example 36	1-121-12	2-1932-193	3.73.7	4.74.7	5.55.5	0.1350.135	0.0520.052	10.510.5

Referring to Table 2, in the case of the organic light emitting diode according to the present invention, the driving voltage Volt is equal to or less than the comparative example (low driving voltage), and the light emission efficiency (Cd / A) is improved. have.

Claims

A first electrode;

Second electrode; And

An organic electroluminescent device comprising at least one 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 (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 , 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 alken having 2 to 30 carbon atoms Nyl group, substituted or unsubstituted 2 to 30 carbon atoms Alkynyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C2-C30 heteroalkyl groups, substituted or unsubstituted C7-C30 aralkyl groups, substituted or unsubstituted C6-C30 of Aryl groups, substituted or unsubstituted 6 to 30 carbon atoms Heteroaryl group, substituted or unsubstituted 6 to 30 carbon atoms A heteroarylalkyl group, a substituted or unsubstituted C1-C30 alkylsilyl group, a substituted or unsubstituted C6-C30 arylsilyl group, and a substituted or unsubstituted C6-C30 aryloxy group,

[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 as 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 heteroarylene groups, a substituted or unsubstituted carbon number 2-10 alkylene group, substituted or unsubstituted C2-C10 cycloalkylene group, substituted or unsubstituted C2-C10 alkenylene group, substituted or unsubstituted C2-C10 cycloalkenylene group substituted or unsubstituted C2-C10 heteroalkylene group, substituted or unsubstituted C2-C10 heterocycloalkylene group, substituted or unsubstituted C2-C10 heteroalkenylene group, and substituted or unsubstituted C2-C10 heterocycloalkenylene Is selected from the group consisting of groups,

Ar 1 and Ar 2 are the same as 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 , Substituted or unsubstituted C1-C20 cycloalkyl group, substituted or unsubstituted C1-C20 heteroalkyl group, substituted or unsubstituted C1-C20 heterocycloalkyl group, substituted or unsubstituted C1-C20 alkenyl group, 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 as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a 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 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 cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted An alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted carbon number 6 to 30 aryl groups, substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms, substituted or unsubstituted heteroarylalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted carbon atoms 1 to 30 30 alkylamino group, substituted or unsubstituted C6-C30 arylamino group, substituted or unsubstituted C6-C30 ar A substituted or unsubstituted hetero arylamino group having 2 to 24 carbon atoms, 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 carbon group having 6 to 30 carbon atoms It may be further substituted with one or more substituents selected from the group consisting of an aryloxy group, when the substituents are a plurality, they are the same or different from each other.
The method of claim 1,

The compound represented by Formula 1 is an organic light emitting device that is a compound represented by the formula (3):

[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 group having 1 to 10 carbon atoms 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, 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 , May be further substituted with one or more substituents selected from the group consisting of an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms and a heteroalkyl group having 2 to 30 carbon atoms, and when the substituents are plural, Same or different,

n is an integer of 1 to 3,

R 1 to R 8 are as defined in claim 1.
The method of 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 the formula (5),

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 groups having 2 to 30 carbon atoms, substituted or unsubstituted 2 to 24 carbon atoms Alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted 6 to 30 carbon atoms Aryl group, substituted or unsubstituted C 2 -C 30 Heteroaryl group, substituted or unsubstituted C 6 -C 30 heteroarylalkyl group substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and arylsilyl group having 6 to 30 carbon atoms, or Ar 3 and Ar 4 May be connected to each other to form a 6 to 18 membered ring containing one or more N, O or S,

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, alkyl group of 1 to 30 carbon atoms, of 2 to 30 carbon atoms Alkenyl groups, alkynyl groups of 2 to 24 carbon atoms, cycloalkyl groups of 3 to 30 carbon atoms, heteroalkyl groups of 2 to 30 carbon atoms, aralkyl groups of 7 to 30 carbon atoms, aryl groups of 6 to 30 carbon atoms, heteroaryl of 2 to 30 carbon atoms Group, C3-C30 heteroarylalkyl group, C1-C30 alkoxy group, C1-C30 alkylamino group, C6-C30 arylamino group, C6-C30 aralkylamino group, C2-C24 hetero At least one substituent selected from the group consisting of an arylamino group, 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.
The method of claim 3, wherein

Ar 3 and Ar 4 is an organic light emitting device which is a substituent selected from the group consisting of compounds represented by the following formulas (6) to (11):

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

here,

* Is the combination

p is an integer from 0 to 4,

q is an integer of 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 are each independently 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 as 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 C 3 to 30 Of cycloalkyl group, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 2 to 24 carbon atoms Alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted 6 to 30 carbon atoms Aryl group, substituted or unsubstituted C 2 -C 30 Heteroaryl group, substituted or unsubstituted C 6 -C 30 heteroarylalkyl group substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and arylsilyl group having 6 to 30 carbon atoms,

R 19 to R 21 are each 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 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 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, heteroarylaryl group having 2 to 24 carbon atoms At least one substituent 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.
The method of claim 3, wherein

When M is a functional group represented by Formula 5, Ar 3 and Ar 4 Is an organic electroluminescent device which is connected to N of M to form a ring and is a compound represented by any one of Formula 12 or 13 below:

[Formula 5]

[Formula 12]

[Formula 13]

here,

X 8 and X 9 are the same as or different from each other, and are 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 as 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 C 3 to 30 Of cycloalkyl group, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 2 to 24 carbon atoms Alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted 6 to 30 carbon atoms Aryl group, substituted or unsubstituted C 2 -C 30 Heteroaryl group, substituted or unsubstituted C 6 -C 30 heteroarylalkyl group substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms and arylsilyl group having 6 to 30 carbon atoms, or

R 25 to R 26 are each 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 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 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, heteroarylaryl group having 2 to 24 carbon atoms At least one substituent 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.
The method of claim 1,

The compound represented by Chemical Formula 2 is an organic light emitting device that is a compound represented by the following Chemical Formula 14:

[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.
The method of claim 6,

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 heteroatoms having 6 to 30 heteroatoms. .
The method of claim 6,

At least one of Ar 1 and Ar 2 is an organic light emitting device which is a compound represented by Formula 15:

[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 as 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, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon group having 2 to 24 carbon atoms Alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted 6 to 30 carbon atoms Aryl group, substituted or unsubstituted C 2 -C 30 Heteroaryl group, substituted or unsubstituted C 6 -C 30 heteroarylalkyl group Substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms and arylsilyl group having 6 to 30 carbon atoms, selected from the group consisting of saturated or unsaturated with adjacent groups Can form additional condensed rings,

The R 27 to R 34 and the saturated or unsaturated condensed ring further formed by them are each independently hydrogen, deuterium, urethane group, carboxy group, cyano group, nitro group, halogen group, hydroxy group, carboxylate group, or 1 to C 30 alkyl group, C2-C30 alkenyl group, C2-C24 alkynyl group, C3-C30 cycloalkyl group, C2-C30 heteroalkyl group, C7-C30 aralkyl group, C6-C30 aryl Group, C2-C30 heteroaryl group, C3-C30 heteroarylalkyl group, C1-C30 alkoxy group, C1-C30 alkylamino group, C6-C30 arylamino group, C6-C30 ar An alkylamino group, a heteroarylaryl group having 2 to 24 carbon atoms, 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. It may be further substituted with one or more substituents selected from the group consisting of, when the substituents are a plurality, they are the same or different from each other.
The organic light emitting device of claim 8, wherein Chemical Formula 15 is a compound represented by Chemical Formula 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 of 0 to 6,

g is an integer of 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, a halogen, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number 3 to 30 Of cycloalkyl group, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 2 to 24 carbon atoms Alkynyl group, substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon group having 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted 6 to 30 carbon atoms Aryl group, substituted or unsubstituted C 2 -C 30 Heteroaryl group, substituted or unsubstituted C 6 -C 30 heteroarylalkyl group substituted or unsubstituted alkyl 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 as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted carbon number 6 to 30 An organic electroluminescent device selected from the group consisting of aryl groups.
The method of claim 1,

The compound represented by Formula 1 is an organic light emitting device selected from the group consisting of the following compounds:
The method of claim 1,

The compound represented by Formula 2 is an organic light emitting device selected from the group consisting of the following compounds:
The method of claim 1,

The light emitting layer includes a dopant and a host,

The dopant includes a compound represented by the following Formula 1,

The host is an organic electroluminescent device comprising a compound represented by the following formula (2):

[Formula 1]

[Formula 2]

here,

L 1 , R 1 to R 8 , R 11 to R 20 are as defined in claim 1.