KR102249719B1 - An organic compound and an organic light emitting diode - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic light-emitting device including the same, and more particularly, to an organic compound having excellent lifespan, efficiency, electrochemical stability, and thermal stability, and an organic electroluminescent device including the same.

Description

An organic compound and an organic light emitting diode comprising the same

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

The organic electroluminescent device (OLED) has a simple structure compared to other flat panel display devices such as conventional liquid crystal display devices (LCD), plasma display panels (PDP), and field emission displays (FED), and has various advantages in the manufacturing process. High luminance and viewing angle characteristics are excellent, response speed is fast, and driving voltage is low, so it is actively developed and commercialized to be used as a light source for flat panel displays such as wall-mounted TVs or backlights of displays, lighting, and billboards.

As for the organic electroluminescent device, the first organic EL device reported (CW Tang, SA Vanslyke, Applied Physics Letters, Vol. 51, page 913, 1987) by Eastman Kodak Corporation's CW Tang, etc., and its luminous principle is generally, When a voltage is applied, holes injected from the anode and electrons injected from the cathode recombine to form excitons, an electron-hole pair, and the energy of the excitons is converted into light by transferring the energy of the excitons to the light emitting material.

More specifically, the organic electroluminescent device has a structure including a cathode (electron injection electrode) and an anode (hole injection electrode), and at least one organic layer between the two electrodes. At this time, the organic electroluminescent device is a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL) or an electron from the anode. It is stacked in the order of an electron injection layer (EIL), and an electron blocking layer (EBL) or a hole blocking layer (HBL) is added to the front and rear of the emission layer to increase the efficiency of the emission layer. Can be included as.

Materials used in the organic layer of the organic electroluminescent device are pure organic materials or complex compounds in which organic materials and metals form a complex, and depending on the use, hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electrons. It can be classified into injection materials, etc.

Here, as a hole injection material or a hole transport material, an organic material that is easily oxidized and has an electrochemically stable state upon oxidation is mainly used. As an electron injection material or an electron transport material, an organic material that is easily reduced and has an electrochemically stable state at the time of reduction is mainly used.

On the other hand, as the light emitting layer material, a material having a stable form in both oxidized and reduced states is preferable, and a material having high luminous efficiency that converts excitone to light when it is formed is preferable. More specifically, the light emitting layer is composed of two materials, a host and a dopant, and the dopant must have high quantum efficiency, and the host material has an energy gap larger than that of the dopant material so that energy transfer to the dopant can easily occur. It is desirable. Displays used in TVs and mobiles implement full color in three colors of red, green, and blue, and the emitting layer is composed of red host/dopant, green host/dopant, and blue host/dopant, respectively. It is composed.

As for the existing blue dopant, the use of fluorescent molecules such as Perylene, Coumarine, Anthracene, and Pyrene took up a large portion, but the emission spectrum and full width of the dopant were used. The width half the maximum) is wide, so there is a disadvantage that pure blue light cannot be used during device fabrication. This characteristic is the main reason not only to reduce the efficiency of blue in the resonance structure of the device, but also to make it difficult to utilize the deep blue section.

Recently, a document using a boron-based dopant having a narrow emission spectrum and high device efficiency is published in Adv. Mater. 2016, 28, 2777-2781 and Angew. Chem. Int. It was published in Ed 2017, 56, 5087-5090, and disclosed in Korean Laid-Open Patent Publication No. 10-2016-0119683. In the case of the previously introduced boron-based blue dopant material, boron atoms are included in the center and are cyclized. As a result, the structure of the molecule is maintained in a planar state as boron forms only a tri-coordinate bond.

Such a planar dopant has an advantage of being able to emit pure light because the energy level of the vibration mode of the molecule is similar, so that the emission spectrum and the half width are narrowed.

(Non-Patent Document 1) Krebs, Frederik C., et al. "Synthesis, Structure, and Properties of 4, 8, 12- Trioxa-12c-phospha-4, 8, 12, 12c-tetrahydrodibenzo [cd, mn] pyrene, a Molecular Pyroelectric." Journal of the American Chemical Society 119.6 (1997): 1208-1216.

An object of the present invention is to provide a novel organic compound and an organic electroluminescent device including the same.

Another object of the present invention is to provide a novel compound that can be used as an emission layer material as an organic compound having a narrow emission spectrum and half width.

Another object of the present invention is to use an organic compound having excellent lifespan, efficiency, electrochemical stability, and thermal stability, so that the driving voltage is low, the efficiency is high in the low-doping section, and the efficiency decrease is relatively suppressed even in the over-doping section, and in particular, the lifetime It is intended to provide an organic electroluminescent device having excellent characteristics such as.

Another object of the present invention is to provide a blue host/dopant system and an organic electroluminescent device suitable for AM-OLED using the organic compound.

In order to achieve the above object, the present invention is to provide a compound represented by the following formula (1):

[Formula 1]

here,

n, m, o and p are the same as or different from each other, and each independently an integer of 0 or 1,

n+m+o+p is an integer of 2 or more,

Y ₁ and Y ₂ are the same as or different from each other, and each independently B, N, C(R ₁ )(R ₂ ), P=O or P=S,

X ₁ to X ₄ are the same as or different from each other, and each independently B(R ₃ ), N(R ₄ ), O, S or Se,

A, B, C, D and E are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

At least one of A, B, C, D and E is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

The R ₁ to R ₄ are the same as or different from each other, and each independently hydrogen, a cyano group, a trifluoromethyl group, a nitro group, a halogen group, a hydroxy group, a substituted or unsubstituted C 1 to C 4 alkylthio group, a substituted or Unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C2-C30 alkenyl group, substituted or unsubstituted C2-C24 alkynyl group, substituted Or an unsubstituted C7 to C30 aralkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, a substituted or unsubstituted C3 to C20 hetero Cycloalkyl group, substituted or unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted 6 carbon atoms To 30 arylamino group, substituted or unsubstituted C6-C30 aralkylamino group, substituted or unsubstituted C2-C24 heteroarylamino group, substituted or unsubstituted C1-C30 alkylsilyl group, substituted or It is selected from the group consisting of an unsubstituted C6-C30 arylsilyl group and a substituted or unsubstituted C6-C30 aryloxy group, and may form a substituted or unsubstituted ring by bonding with adjacent groups.

In addition, the present invention is a first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the one or more organic material layers contains a compound represented by Formula 1 above. The device is provided.

For example, the organic electroluminescent device may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like. However, the structure of the organic electroluminescent device is not limited thereto, and may include a smaller number of organic material layers.

According to a preferred embodiment of the present invention, the organic material layer is an emission layer, and the emission layer may be characterized in that it includes a compound represented by Formula 1 above.

According to a preferred embodiment of the present invention, the organic material layer is a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, a hole transport layer, or an electron blocking layer comprises a compound represented by Formula 1 above. can do.

In the present invention, "hydrogen" is hydrogen, light hydrogen, deuterium or tritium.

In the present specification, "halogen group" is fluorine, chlorine, bromine or iodine.

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

In the present invention, “alkynyl” refers to a monovalent substituent derived from a straight or branched 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 and 2-propynyl.

In the present invention, "alkylthio" refers to the above-described alkyl group bonded through a sulfur linkage (-S-).

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

In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 6 to 30 carbon atoms. At this time, at least one carbon, preferably 1 to 3 carbons in the ring is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, phenoxathienyl, indolizinyl, indolyl ( indolyl), purinyl, quinolyl, benzothiazole, polycyclic rings such as 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-, and R means an aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R'refers to alkyl having 1 to 40 carbon atoms, and has a linear, branched, or cyclic structure It may include. Examples of the 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, "alkoxy" may be a straight chain, branched chain or cyclic chain. Although the number of carbon atoms of the alkoxy is not particularly limited, it is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. May be, but is not limited thereto.

In the present invention, "aralkyl" refers to an aryl-alkyl group in which aryl and alkyl are as described above. Preferred aralkyls include lower alkyl groups. Non-limiting examples of suitable aralkyl groups include benzyl, 2-phenethyl and naphthalenylmethyl. Binding to the parent moiety is made through alkyl.

In the present invention, “arylamino group” refers to an amine substituted with an aryl group having 6 to 30 carbon atoms.

In the present invention, "alkylamino group" refers to an amine substituted with an alkyl group having 1 to 30 carbon atoms.

In the present invention, "aralkylamino group" refers to an amine substituted with an aryl-alkyl group having 6 to 30 carbon atoms.

In the present invention, “heteroarylamino group” refers to an aryl group having 6 to 30 carbon atoms and an amine group substituted with a heterocyclic group.

In the present invention, "heteroaralkyl group" refers to an aryl-alkyl group substituted with a heterocyclic group.

In the present invention, "cycloalkyl" refers to 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, and adamantine.

In the present invention, “heterocycloalkyl” refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 carbon atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S or Se Is substituted with a hetero atom such as. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

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

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

In the present invention, "adjacent 　 groups are bonded to each other to form a ring" means 　adjacent 　 groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Substituted or unsubstituted aromatic heterocycle; Or it means to form a condensed ring of these.

In the present specification, “alicyclic compound” has the same meaning as “aliphatic hydrocarbon ring”, and refers to a ring consisting of only carbon and hydrogen atoms as a non-aromatic ring.

In the present specification, “hetero-alicyclic compound” refers to an alicyclic compound including at least one heteroatom by substitution of at least one of carbons of the “aliphatic hydrocarbon ring” with a hetero atom.

Examples of the "aromatic hydrocarbon ring" in the present specification include a phenyl group, a naphthyl group, an anthracenyl group, and the like, but are not limited thereto.

In the present specification, "aliphatic heterocycle" refers to an aliphatic ring including one or more of heteroatoms.

In the present specification, "aromatic heterocycle" refers to an aromatic ring including one or more of heteroatoms.

In the present specification, an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, an aliphatic heterocycle, and an aromatic heterocycle may be monocyclic or polycyclic.

In the present specification, "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other. The substituent is hydrogen, cyano group, nitro group, halogen group, hydroxy 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, heteroalkyl group having 2 to 30 carbon atoms, 6 to carbon atoms 30 aralkyl group, C5 to C30 aryl group, C2 to C30 heteroaryl group, C3 to C30 heteroarylalkyl group, C1 to C30 alkoxy group, C1 to C30 alkylamino group, C6 to C6 It may be substituted with one or more substituents selected from the group consisting of an arylamino group of 30, an aralkylamino group having 6 to 30 carbon atoms, and a hetero arylamino group having 2 to 24 carbon atoms, but is not limited to the above examples.

In the present specification, "bonding with adjacent groups to form a ring" refers to a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocycle, a substituted Or it means to form an unsubstituted aromatic heterocycle or a condensed ring thereof.

The present invention provides a novel compound that can be used as an emission layer material or the like as an organic compound having a narrow emission spectrum and half width.

The present invention provides an organic electroluminescent device having a low driving voltage and remarkably improving color reproducibility by using an organic compound having excellent lifespan, efficiency, electrochemical stability, and thermal stability.

In addition, the present invention provides a blue host/dopant system and an organic electroluminescent device suitable for AM-OLED using the organic compound.

delete

Hereinafter, embodiments of the present invention will be described in detail so that those of ordinary skill in the art can easily implement the present invention. However, the present invention may be implemented in various different forms and is not limited to the embodiments described herein.

The organic compound according to the present invention has a planar structure and minimizes the mutual attraction of pi (π -π) of molecules in the molecule, while the energy level of the vibration mode of the molecule is almost similar, so that a narrow emission spectrum and By having a half width, the color gamut can be remarkably improved.

The organic compound according to the present invention, including atoms that provide a planar structure, such as boron-based elements, interferes with the formation of excimers in the molecule, and increases the electron density of the core and the stability of the dopant, thereby increasing the efficiency and lifetime of the device. Can be made possible.

Specifically, it relates to a compound represented by the following formula 1:

[Formula 1]

here,

n, m, o and p are the same as or different from each other, and each independently an integer of 0 or 1,

n+m+o+p is an integer of 2 or more,

Y ₁ and Y ₂ are the same as or different from each other, and each independently B, N, C(R ₁ )(R ₂ ), P=O or P=S,

X ₁ to X ₄ are the same as or different from each other, and each independently B(R ₃ ), N(R ₄ ), O, S or Se,

A, B, C, D and E are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

At least one of A, B, C, D and E is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

The R ₁ to R ₄ are the same as or different from each other, and each independently hydrogen, a cyano group, a trifluoromethyl group, a nitro group, a halogen group, a hydroxy group, a substituted or unsubstituted C 1 to C 4 alkylthio group, a substituted or Unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C2-C30 alkenyl group, substituted or unsubstituted C2-C24 alkynyl group, substituted Or an unsubstituted C7 to C30 aralkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, a substituted or unsubstituted C3 to C20 hetero Cycloalkyl group, substituted or unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted 6 carbon atoms To 30 arylamino group, substituted or unsubstituted C6-C30 aralkylamino group, substituted or unsubstituted C2-C24 heteroarylamino group, substituted or unsubstituted C1-C30 alkylsilyl group, substituted or It is selected from the group consisting of an unsubstituted C6-C30 arylsilyl group and a substituted or unsubstituted C6-C30 aryloxy group, and may form a substituted or unsubstituted ring by bonding with adjacent groups.

At least one of A, C, and E may be a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

Specifically, the heteroaryl group is a substituted or unsubstituted pyrrole, a substituted or unsubstituted furan, a substituted or unsubstituted thiophene, a substituted or unsubstituted dioxin, a substituted or unsubstituted oxatiin, a substituted or unsubstituted dithione Phosphorus, substituted or unsubstituted indole, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene, substituted or unsubstituted benzodioxin, substituted or unsubstituted benzoxatiine, substituted or unsubstituted benzo Dithiine, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzodioxin, substituted or unsubstituted phenoxanthine, substituted or It may be selected from the group consisting of unsubstituted thianthrene, and when the heteroaryl group is substituted, adjacent substituents may be connected to each other to form a cyclic compound.

More specifically, the A, C and E may be the same as or different from each other, and each independently may be a compound represented by the following Formula 2 or Formula 3:

[Formula 2]

[Formula 3]

here,

X ₅ to X ₁₀ and X ₁₂ to X ₁₅ are the same as or different from each other, and each independently _{selected from the group consisting of C (R 5} ), N, S and O,

X ₁₁ is selected from the group consisting of C(R ₆ )(R ₇ ), N(R ₈ ), S and O,

R ₅ to R ₈ are the same as or different from each other, and each independently hydrogen, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, substituted or unsubstituted A substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C24 alkynyl group, a substituted or Unsubstituted C7 to C30 aralkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C60 heteroaryl group, substituted or unsubstituted C6 to C30 heteroaryl Alkyl group, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms Aralkylamino group, substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms and substituted or unsubstituted It is selected from the group consisting of a substituted aryloxy group having 6 to 30 carbon atoms, and may be bonded to adjacent groups to form a substituted or unsubstituted ring.

Specifically, when A, C, and E are all made of Formula 2, all of X ₅ to X ₁₀ are not C(R ₅ ).

When all of A, C, and E are made of Chemical Formula 3, X ₁₁ is C(R ₆ )(R ₇ ), and at the same time, X ₁₂ to X ₁₅ cannot all be C(R _{5 ).}

When both of X ₅ to X ₁₀ and X ₁₂ to X ₁₅ are C(R ₅ ), X ₁₁ is not C(R ₆ )(R ₇ ).

The C may be selected from the group consisting of the following Chemical Formulas 4 to 7:

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

here,

Four groups of Y ₁ to Y ₆ are a moiety bonded to an adjacent group,

Y ₁ to Y ₆ that do not bind to adjacent groups are the same or different from each other, and are each independently _{selected from the group consisting of C (R 9} ), N, S and O,

Two groups of Y ₇ to Y ₁₀ are a moiety bonded to an adjacent group,

Y ₇ to Y ₁₀ that do not bind to adjacent groups are the same or different from each other, and are each independently _{selected from the group consisting of C (R 10} ), N, S and O,

Two groups of Y ₁₁ to Y ₁₄ are a moiety bonded to an adjacent group,

Y ₁₁ to Y ₁₄ that do not bind to adjacent groups are the same or different from each other, and are each independently _{selected from the group consisting of C (R 11} ), N, S and O,

Two groups of Y ₁₅ to Y ₁₈ are a moiety bonded to an adjacent group,

Y ₁₅ to Y ₁₈ that do not bind to adjacent groups are the same or different from each other, and are each independently _{selected from the group consisting of C (R 12} ), N, S and O,

Two groups of Y ₁₉ to Y ₂₂ are a moiety bonded to an adjacent group,

Y ₁₉ to Y ₂₂ that do not bind to adjacent groups are the same or different from each other, and are each independently _{selected from the group consisting of C (R 13} ), N, S and O,

Two groups of Y ₂₃ to Y ₂₆ are a moiety bonded to an adjacent group,

Y ₂₃ to Y ₂₆ that do not bind to adjacent groups are the same or different from each other, and are each independently _{selected from the group consisting of C (R 14} ), N, S and O,

Two groups of Y ₂₇ to Y ₃₀ are a moiety bonded to an adjacent group,

Y ₂₇ to Y ₃₀ that do not bind to adjacent groups are the same or different from each other, and are each independently _{selected from the group consisting of C (R 15} ), N, S and O,

X ₁₆ to X ₁₈ are the same as or different from each other, and each independently _{selected from the group consisting of C (R 16} ) (R ₁₇ ) N (R ₁₈ ), S and O,

R ₉ to R ₁₈ are the same as or different from each other, and each independently hydrogen, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, substituted or unsubstituted A substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C24 alkynyl group, a substituted or Unsubstituted C7 to C30 aralkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C60 heteroaryl group, substituted or unsubstituted C6 to C30 heteroaryl Alkyl group, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms Aralkylamino group, substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms and substituted or unsubstituted It is selected from the group consisting of a substituted aryloxy group having 6 to 30 carbon atoms, and may be bonded to adjacent groups to form a substituted or unsubstituted ring.

The A and E may be the same as or different from each other, and each independently may be a compound selected from the group consisting of the following Formulas 8 to 11:

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

here,

q and r are integers from 0 to 4,

Two groups of Y ₃₁ to Y ₃₆ are a moiety bonded to an adjacent group,

Y ₃₁ to Y ₃₆ that do not bond with an adjacent group are the same or different from each other, and are each independently _{selected from the group consisting of C (R 21} ), N, S and O,

Two groups of Y ₃₇ to Y ₄₀ are a moiety bonded to an adjacent group,

Y ₃₇ to Y ₄₀ that do not bind to adjacent groups are the same or different from each other, and are each independently _{selected from the group consisting of C (R 22} ), N, S and O,

Y ₄₁ and Y _42- is a moiety bonded to an adjacent group,

Two groups of Y ₄₃ to Y ₄₆ are a moiety bonded to an adjacent group,

Y ₄₃ to Y ₄₆ that do not bind to an adjacent group are the same or different from each other, and are each independently _{selected from the group consisting of C (R 23} ), N, S and O,

X ₁₉ and X ₂₁ are the same as or different from each other, each independently _{selected from the group consisting of C (R 24} ) (R ₂₅ ), N (R ₂₆ ), S and O,

R ₁₉ to R ₂₆ are the same as or different from each other, and each independently hydrogen, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, substituted or unsubstituted A substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C24 alkynyl group, a substituted or Unsubstituted C7 to C30 aralkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C60 heteroaryl group, substituted or unsubstituted C6 to C30 heteroaryl Alkyl group, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms Aralkylamino group, substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms and substituted or unsubstituted It is selected from the group consisting of a substituted aryloxy group having 6 to 30 carbon atoms, and may be bonded to adjacent groups to form a substituted or unsubstituted ring.

The Y ₁ and Y ₂ are the same as or different from each other, and each independently B or N.

B and D are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

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

The compound of Formula 1 of the present invention may be usefully used as a dopant material for an emission layer. Specifically, the organic compound is a dopant material, which is thermally stable compared to the conventional boron-based dopant, and has a narrow emission spectrum and half width, thereby providing an organic compound that can significantly improve color reproducibility.

The organic compound of the present invention can be usefully used as a material for forming a light emitting layer. In the above, the material for forming the light-emitting layer may further include a material commonly added when the organic compound is manufactured in a form necessary for use in forming the light-emitting layer, such as a host material.

The material for forming the light emitting layer may be a material for a dopant.

The present invention provides an organic electroluminescent device including the compound represented by Chemical Formula 1.

The organic compound of the present invention can be usefully used as a material for forming a hole injection layer, a hole transport layer, or an electron blocking layer.

In addition, the present invention relates to a material for forming a light emitting layer comprising the organic compound.

In the above, the material for forming the light-emitting layer may further include a material commonly added when the organic compound is manufactured in a form necessary for use in forming the light-emitting layer, such as a host material.

In addition, the present invention is an organic electroluminescent device in which an organic thin film layer consisting of one or more layers including at least a light emitting layer is stacked between a cathode and an anode,

It relates to an organic electroluminescent device, characterized in that the light emitting layer contains the organic compound represented by Formula 1 alone or in combination of two or more.

The organic electroluminescent device may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are stacked, and an electron blocking layer, a hole blocking layer, etc. are additionally stacked if necessary Can be.

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 electroluminescent device of the present invention.

The organic electroluminescent device of the present invention may have a structure in which an anode (hole injection electrode), a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), and a cathode (electron injection electrode) are sequentially stacked, Preferably, it may further include an electron blocking layer (EBL) between the anode and the emission layer, and an electron transport layer (ETL) and an electron injection layer (EIL) between the cathode and the emission layer. In addition, a hole blocking layer (HBL) may be further included between the cathode and the emission layer.

In the method of manufacturing an organic light emitting diode according to the present invention, first, an anode is formed by coating a material for an anode on a substrate surface in a conventional manner. At this time, the substrate to be used is preferably a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling and waterproofness. In addition, as a material for the anode, 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 with a hole injection layer (HIL) material in a conventional manner. Materials for the hole injection layer include copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(3-methylphenyl). Amino)phenoxybenzene (m-MTDAPB), starburst type amines 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), 4,4',4"-tris Examples include (N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA) or IDE406 available from Idemitsu.

A hole transport layer (HTL) is formed on the surface of the hole injection layer by vacuum thermal evaporation or spin coating in a conventional manner. At this time, the hole transport layer material is 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) is exemplified.

A light emitting layer is formed by vacuum thermal evaporation or spin coating on the surface of the hole transport layer with a light emitting layer (EML) material in a conventional manner. At this time, as a single light-emitting material or a light-emitting host material among the light-emitting layer materials used, tris (8-hydroxyquinolinolato) aluminum (Alq ₃ ), etc. may be used in the case of green, and Alq ₃ , CBP (4, 4'-N,N'-dicabazole-biphenyl, 4,4'-N,N'-dicarbazole-biphenyl), PVK(poly(n-vinylcabazole), poly(n-vinylcarbazole)), ADN( 9,10-di(naphthalene-2-yl)anthracene, 9,10-di(naphthalen-2-yl)anthracene), TCTA, TPBI(1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene , 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene), TBADN(3-tert-butyl-9,10-di(naphth-2-yl) anthracene, 3-tert-butyl -9,10-di (naphth-2 days) anthracene), E3, DSA (distyrylarylene, distyrylarylene), or a mixture of two or more thereof may be used, but the present invention is not limited thereto.

In the case of a dopant that can be used together with a light emitting host among the light emitting layer materials, the compound of the present invention may be preferably used.

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

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

Optionally, by additionally forming a hole blocking layer (HBL) between the light emitting layer and the electron transport layer and using a phosphorescent dopant in the light emitting layer together, it is possible to prevent the phenomenon that triplet excitons or holes are diffused into the electron transport layer. .

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). To) lithium (Liq), bis(8-hydroxy-2-methylquinolinolnato)-aluminum biphenoxide (BAlq), bathocuproine (BCP), and LiF may be used.

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

A negative electrode is formed by vacuum thermal evaporation of a negative electrode material on the surface of the electron injection layer in a conventional manner.

At this time, the negative electrode materials used are lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), and magnesium-silver. (Mg-Ag) and the like can be used. In addition, in the case of a top emission organic electroluminescent device, indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode through which light can pass. A capping layer CPL may be formed on the surface of the cathode.

Hereinafter, a method for synthesizing the compounds will be described below with a representative example. However, the method for 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 exemplified below and methods known in the art.

[Synthesis Example 1-1]

Starting material 1-1 compound 1

Starting material 1-1 11.94g (10.0mmol), orthodichlorobenzene (30ml) and Boron tribromide 4.82 mL (50.0 mmol) were added to a high pressure reactor and stirred. The reaction mixture was heated to 180°C to 190°C and stirred for 12 hours.

After cooling the reaction solution to room temperature, cooled water was added, and the organic layer was extracted using Ethyl acetate. The solvent of the extracted organic layer _{was dried over MgSO 4} and then filtered. After the filtrate was concentrated under reduced pressure, it was purified using a silica gel column chromatography (DCM/Hexane) method.

After recrystallization and purification with a DCM/Acetone mixed solvent, 0.97 g of Compound 1 was obtained in 8% yield.

MS (MALDI-TOF) m/z: 1209 [M]+

[Synthesis Example 1-2]

Starting material 1-2 compound 2

Synthesized in the same manner as in the preparation of compound 1, except that 11.61 g (10.0 mmol) of starting material 1-2 was used instead of starting material 1-1, and 1.06 g of compound 2 was obtained in 9% yield.

MS (MALDI-TOF) m/z: 1176 [M]+

[Synthesis Example 1-3]

Starting material 1-3 compound 66

Synthesized in the same manner as in the preparation of compound 1, except that 12.47 g (10.0 mmol) of starting material 1-3 was used instead of starting material 1-1, and 1.14 g of compound 66 was obtained in 9% yield.

MS (MALDI-TOF) m/z: 1262 [M]+

[Synthesis Example 1-4]

Starting material 1-4 compound 46

Synthesized in the same manner as in the preparation of compound 1, except that 12.89 g (10.0 mmol) of starting material 1-4 was used instead of starting material 1-1, and 1.30 g of compound 46 was obtained in 10% yield.

MS (MALDI-TOF) m/z: 1304 [M]+

[Synthesis Example 1-5]

Starting material 1-5 compound 161

Synthesized in the same manner as in the preparation of compound 1, except that 11.88 g (10.0 mmol) of starting material 1-5 was used instead of starting material 1-1, and 1.32 g of compound 161 was obtained in 11% yield.

MS (MALDI-TOF) m/z: 1203 [M]+

[Synthesis Example 1-6]

Starting material 1-6 compound 121

Synthesized in the same manner as in the preparation of compound 1, except that 11.71 g (10.0 mmol) of starting material 1-6 was used instead of starting material 1-1, and 1.07 g of compound 121 was obtained in 9% yield.

MS (MALDI-TOF) m/z: 1187 [M]+

[Synthesis Example 1-7]

Starting material 1-7 compound 111

After dissolving in 11.82g (10.0mmol) of starting material 1-7 and tert- Butylbenzene (42 ml), the mixture was cooled to 0 °C. 12.0 mL (30.0 mmol) of a 2.5M n- Butyllithium solution (in hexane) was added under a nitrogen atmosphere, and the mixture was stirred at room temperature for 3 hours.

After that, the reaction mixture was cooled to 0° C., and 2.89 mL (30.0 mmol) of Boron tribromide was added, followed by stirring at room temperature for 0.5 hours. Again, the reaction was cooled to 0°C, and 6.97 mL (40mmol) of N,N-Diisopropylethylamine was added, followed by stirring at 60 to 70°C for 2 hours.

The reaction solution was cooled to room temperature, and the organic layer was extracted using Ethyl acetate and Water. The solvent of the extracted organic layer _{was dried over MgSO 4} and then filtered. After the filtrate was concentrated under reduced pressure, it was purified using a silica gel column chromatography (DCM/Hexane) method.

After recrystallization and purification with a DCM/Acetone mixed solvent, 0.94 g of the compound 111 was obtained in a 9% yield.

MS (MALDI-TOF) m/z: 1039 [M]+

[Synthesis Example 1-8]

Starting material 1-8 compound 47

Synthesis was carried out in the same manner as in the preparation of compound 111, except that 10.86 g (10.0 mmol) of starting material 1-8 was used instead of starting material 1-7, and 0.66 g of compound 47 was obtained in a 7% yield.

MS (MALDI-TOF) m/z: 943 [M]+

[Synthesis Example 1-9]

Compound 47 compound 48

Compound 47 0.94g (1.0mmol), phenoxazine 0.46g (2.5mmol) and sodium tert butoxide 0.288g (3.0mmol) tris (dibenzylideneacetone) dipalladium (0) 0.046g (0.05mmol), 2-dish Clohexyl phosphino-2′,6′-dimethoxybiphenyl 0.041 g (0.1 mmol) and toluene 100 mL were added and stirred to reflux. After completion of the reaction, the toluene layer was extracted using 50 mL of water.

The reaction solution was cooled to room temperature, and the organic layer was extracted using ethyl acetate and water. The solvent of the extracted organic layer _{was dried over MgSO 4} and then filtered. After the filtrate was concentrated under reduced pressure, it was purified using a silica gel column chromatography (DCM/Hexane) method.

After recrystallization and purification with a DCM/acetone mixed solvent, 0.84 g of compound 48 was obtained in a 68% yield.

MS (MALDI-TOF) m/z: 1237 [M]+

[Synthesis Example 1-10]

Compound 1-9 Compound 49

Synthesis was performed in the same manner as in the preparation of compound 48, except that 0.42 g (2.5 mmol) of carbazole was used instead of phenoxyazine, and 0.84 g of compound 49 was obtained in a 70% yield.

MS (MALDI-TOF) m/z: 1205 [M]+

[Synthesis Example 1-11]

Starting material 1-11 compound 112

Synthesized in the same manner as in the preparation of compound 111, except that 12.19 g (10.0 mmol) of starting material 1-11 was used instead of starting material 1-7, and 0.86 g of compound 112 was obtained in 8% yield.

MS (MALDI-TOF) m/z: 1076 [M]+

[Synthesis Example 1-12]

Compound 112 compound 114

Except for using piperidine 0.21g (2.5mmol) instead of phenoxyazine, synthesized in the same manner as in the preparation of compound 48, 0.85 g of compound 114 was obtained in a 72% yield.

MS (MALDI-TOF) m/z: 1174 [M]+

[Synthesis Example 1-13]

Compound 112 compound 115

Synthesized in the same manner as in the preparation of compound 48, except that 0.18 g (2.5 mmol) of pyrrolidine was used instead of phenoxyazine, and 0.84 g of compound 115 was obtained in a 73% yield.

MS (MALDI-TOF) m/z: 1145 [M]+

[Synthesis Example 1-14]

Starting material 1-14 compound 117

Synthesized in the same manner as in the preparation of compound 111, except that 9.13 g (10.0 mmol) of starting material 1-14 was used instead of starting material 1-7, and 0.93 g of compound 117 was obtained in a 12% yield.

MS (MALDI-TOF) m/z: 771 [M]+

[Synthesis Example 1-15]

Compound 117 Compound 118

Synthesis was conducted in the same manner as in the preparation of compound 48, except that 0.5 g (1.0 mmol) of ditolylamine was used instead of phenoxyazine, and 0.87 g of compound 118 was obtained in an 80% yield.

MS (MALDI-TOF) m/z: 1092 [M]+

[Synthesis Example 1-16]

Compound 117 Compound 119

Compound 117 0.77g (1.0mmol), phenol 0.24g (2.5mmol), cesium carbonate 1.6g (5.0mmol), copper (I) 0.03g (0.2mmol), methylpyrrolidone 10 mL were added and stirred to reflux. .

The reaction solution was cooled to room temperature, and the organic layer was extracted using Ethyl acetate and Water. The solvent of the extracted organic layer _{was dried over MgSO 4} and then filtered. After the filtrate was concentrated under reduced pressure, it was purified using a silica gel column chromatography (DCM/Hexane) method.

After recrystallization and purification with a DCM/Acetone mixed solvent, 0.87 g of Compound 119 was obtained in a 76% yield.

MS (MALDI-TOF) m/z: 886 [M]+

[Synthesis Example 1-17]

Starting material 1-17 compound 120

Synthesized in the same manner as in the preparation of compound 111, except that 10.19 g (10.0 mmol) of starting material 1-17 was used instead of starting material 1-7, and 0.81 g of compound 120 was obtained in 11% yield.

MS (MALDI-TOF) m/z: 738 [M]+

[Synthesis Example 1-18]

Compound 120 Compound 196

Synthesized in the same manner as in the preparation of compound 48, except that 0.74 g (1.0 mmol) of compound 120 was used instead of starting material 1-8, and 0.77 g of compound 196 was obtained in a 75% yield.

MS (MALDI-TOF) m/z: 1031 [M]+

[Synthesis Example 1-19]

Compound 120 Compound 133

Compound 120 0.74 g (1.0 mmol) and phenyl boronic acid 0.31 g (2.5 mmol), potassium triphosphate 1.06 g (5.0 mmol), palladium (II) acetate 0.01 g (0.06 mmol), 2-dicyclohexyl phosphino-2 0.05g (0.12 mmol) of ′,6′-dimethoxybiphenyl, toluene (10 mL) and H ₂ O (1 mL) were added and stirred to reflux.

The reaction solution was cooled to room temperature, and the organic layer was extracted using Ethyl acetate and Water. The solvent of the extracted organic layer _{was dried over MgSO 4} and then filtered. After the filtrate was concentrated under reduced pressure, it was purified using a silica gel column chromatography (DCM/Hexane) method.

Thereafter, recrystallization and purification were performed with a DCM/Acetone mixed solvent to obtain 0.66 g of the compound 133 in an 80% yield.

MS (MALDI-TOF) m/z: 821 [M]+

<Example 1: Method for manufacturing an organic electroluminescent device with a rear light emitting structure>

The substrate on which ITO (100 nm), the anode of the organic electroluminescent device, was stacked was divided into a cathode, an anode region, and an insulating layer through a photo-lithograph process, followed by patterning, and then the work function of the anode (ITO) ( For the purpose of increasing work-function) and cleaning, the surface was treated with UV Ozone treatment and O2:N2 plasma. HAT-CN was formed thereon to a thickness of 10 nm as a hole injection layer (HIL). Then, on the hole injection layer, as a hole transport layer, N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4, 4'-diamine was vacuum deposited to a thickness of 90 nm, and N-phenyl-N-(4-(spiro[benzo[de]anthracene-7,9) as an electron blocking layer (EBL) on top of the hole transport layer (HTL) '-Fluorene]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine was formed to a thickness of 15 nm. A light emitting layer (EML) was formed with a thickness of 25 nm by depositing α,β-AND as a host of the light emitting layer on the electron blocking layer (EBL) and at the same time doping Compound 1 by 2% with a dopant.

On it, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole and LiQ were added as an electron transport layer (ETL). 25nm was deposited by mixing at a weight ratio of 1:1, an electron injection layer of 1nm was deposited on the electron transport layer, and aluminum was deposited as a cathode to a thickness of 100nm. Thereafter, an organic electroluminescent device was manufactured by bonding a seal cap including a getter with a UV-curable adhesive to protect the organic electroluminescent device from oxygen or moisture in the atmosphere.

<Examples 2 to 10: Preparation of organic electroluminescent device>

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compounds 2, 66, 46, 161, 121, 48, 49, 114, and 115 were used instead of Compound 1 as a dopant.

<Comparative Example 1: Fabrication of an organic electroluminescent device>

An organic electroluminescent device was manufactured using the same method as in Example 1, except that Compound A was used instead of Compound 1 as a dopant.

<Compound A>

<Characteristic analysis of organic light emitting device>

The following is a result of measuring the electroluminescence characteristics by applying a current of ^{10 mA/cm 2} to the organic electroluminescent device of the rear light emitting structure prepared in Examples 1 to 10 and Comparative Example 1, and measuring the lifetime by driving a constant current of ^{10 mA/cm 2.} It compared with Table 1 and shown.

division DOPANT Voltage(V) Current efficiency
(Cd/A) Life T95
(hr) Example 1 Compound 1 3.98 7.7 188 Example 2 Compound 2 3.95 7.6 147 Example 3 Compound 66 3.96 8.1 105 Example 4 Compound 46 4.00 8.2 101 Example 5 Compound 161 3.88 8.1 123 Example 6 Compound 121 3.92 8.0 140 Example 7 Compound 48 3.90 7.7 105 Example 8 Compound 49 3.89 7.8 140 Example 9 Compound 114 3.95 7.7 127 Example 10 Compound 115 3.94 7.7 114 Comparative Example 1 Compound A 3.95 6.5 94

Compared to the organic electroluminescent device using Compound A as a dopant, it was confirmed that the voltage in the organic electroluminescent device using the compound of the present invention as a dopant material was at the same level, but exhibited excellent effects in current efficiency and lifespan.

delete

<Example 11: Method for manufacturing an organic electroluminescent device with a rear light emitting structure>

The substrate on which ITO (100 nm), the anode of the organic electroluminescent device, was stacked was divided into a cathode, an anode region, and an insulating layer through a photo-lithograph process, followed by patterning, and then the work function of the anode (ITO) ( For the purpose of increasing work-function) and cleaning, the surface was treated with _{UV Ozone treatment and O 2} :N _{2 plasma.} HAT-CN was formed thereon to a thickness of 10 nm as a hole injection layer (HIL). Then, on the hole injection layer, as a hole transport layer, N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4, 4'-diamine was vacuum-deposited to form a thickness of 90 nm, and mCP was formed to a thickness of 15 nm as an electron blocking layer (EBL) on the hole transport layer (HTL). A light emitting layer (EML) was formed with a thickness of 20 nm by depositing Compound B as a host of the light emitting layer on the electron blocking layer (EBL) and at the same time doping Compound 1 by 2% with a dopant.

TSPO1 was deposited at 5 nm as a hole blocking layer (HBL) thereon, and then TPBI at 30 nm was deposited as an electron transport layer (ETL), 1 nm LIF was deposited on the electron transport layer, and aluminum was deposited as a cathode at 50 nm thickness. Thereafter, an organic electroluminescent device was manufactured by bonding a seal cap including a getter with a UV-curable adhesive to protect the organic electroluminescent device from oxygen or moisture in the atmosphere.

<Compound B>

<Examples 12 to 20: Preparation of organic electroluminescent device>

An organic electroluminescent device was manufactured in the same manner as in Example 11, except that Compounds 2, 66, 46, 161, 121, 48, 49, 114, and 115 were used instead of Compound 1 as a dopant.

<Comparative Example 2: Fabrication of an organic electroluminescent device>

An organic electroluminescent device was manufactured using the same method as in Example 8, except that Compound A was used instead of Compound 1 as a dopant.

<Compound A>

<Characteristic analysis of organic light emitting device>

The following is a result of measuring the electroluminescent characteristics by applying a current of ^{10 mA/cm 2} to the organic electroluminescent device of the rear light emitting structure prepared in Examples 11 to 20 and Comparative Example 2, and measuring the lifetime by driving a constant current of ^{10 mA/cm 2.} It compared with Table 2 and shown.

division DOPANT Voltage(V) Current efficiency (Cd/A) Example 11 Compound 1 6.89 15.1 Example 12 Compound 2 6.95 14.8 Example 13 Compound 66 6.98 15.4 Example 14 Compound 46 7.03 15.7 Example 15 Compound 161 6.90 14.8 Example 16 Compound 121 6.94 15.0 Example 17 Compound 48 7.02 15.2 Example 18 Compound 49 7.00 15.4 Example 19 Compound 114 7.01 15.2 Example 20 Compound 115 7.02 15.0 Comparative Example 2 Compound A 7.05 12.6

Compared to the organic electroluminescent device using the compound A as a dopant, it was confirmed that the voltage in the organic electroluminescent device using the compound of the present invention as a dopant material was at the same level, but exhibited an excellent effect in current efficiency.

Although the preferred embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements by those skilled in the art using the basic concept of the present invention defined in the following claims are also present It belongs to the scope of rights of

Claims (9)

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

here,
n, m, o and p are the same as or different from each other, and each independently an integer of 0 or 1,
n+m+o+p is an integer of 2 or more,
Y ₁ and Y ₂ are the same as or different from each other, each independently selected from B or N,
At least one of Y ₁ and Y _{2 is B,}
X ₁ to X ₄ are the same as or different from each other, and each independently B(R ₃ ), N(R ₄ ), O, S or Se,
A, B, C, D and E are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,
At least one of A, C and E is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,
The R ₃ and R ₄ are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C2 To 30 alkenyl groups, substituted or unsubstituted alkynyl groups having 2 to 24 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted A C2-C60 heteroaryl group, a substituted or unsubstituted C3-C20 heterocycloalkyl group, a substituted or unsubstituted C3-C30 heteroarylalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted C1-C30 alkylamino group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C6-C30 aralkylamino group, a substituted or unsubstituted C2-C24 alkylamino group It is selected from the group consisting of a hetero arylamino group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, , May be bonded to each other with adjacent groups to form a substituted or unsubstituted ring,
The substituents of A, B, C, D, E, R ₃ and R ₄ are hydrogen, cyano group, nitro group, halogen group, hydroxy group, alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms, 2 to carbon number 24 alkynyl group, C2 to C30 heteroalkyl group, C6 to C30 aralkyl group, C5 to C30 aryl group, C2 to C30 heteroaryl group, C3 to C30 heteroarylalkyl group, C1 to C1 It may be selected from the group consisting of an alkoxy group of 30, an alkylamino group having 1 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, and a hetero arylamino group having 2 to 24 carbon atoms. The method of claim 1,
At least one of A, C and E is a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms. The method of claim 1,
The A, C, and E are the same as or different from each other, and each independently a compound represented by the following Formula 2 or Formula 3:
[Formula 2]

[Formula 3]

here,
X ₅ to X ₁₀ and X ₁₂ to X ₁₅ are the same as or different from each other, and each independently _{selected from the group consisting of C (R 5} ), N, S and O,
X ₁₁ is selected from the group consisting of C(R ₆ )(R ₇ ), N(R ₈ ), S and O,
R ₅ to R ₈ are the same as or different from each other, and each independently hydrogen, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, substituted or unsubstituted A substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C20 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C24 alkynyl group, a substituted or Unsubstituted C7 to C30 aralkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C60 heteroaryl group, substituted or unsubstituted C6 to C30 heteroaryl Alkyl group, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms Aralkylamino group, substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms and substituted or unsubstituted It is selected from the group consisting of a substituted aryloxy group having 6 to 30 carbon atoms, and may be bonded to adjacent groups to form a substituted or unsubstituted ring. delete The method of claim 1,
The compounds B and D 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 first electrode; A second electrode provided opposite to the first electrode; And an organic material layer of at least one layer provided between the first electrode and the second electrode,
At least one of the one or more organic material layers comprises the compound according to claim 1
Organic electroluminescent device. The method of claim 6,
The organic material layer is selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
Organic electroluminescent device. The method of claim 6,
The organic material layer is an organic electroluminescent device that is a light emitting layer. The method of claim 6,
The organic material layer is an organic electroluminescent device which is a hole injection layer, a hole transport layer, or an electron blocking layer.