TWI488941B - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Description

Novel organic electroluminescent compound and organic electric field illuminating device using the same

The present invention relates to novel organic electroluminescent compounds and organic electric field illuminating devices using the same.

Among display devices, an electric field illumination (EL) device is advantageous in that it has a wide viewing angle, excellent contrast, and fast reaction speed as a self-luminous display device. Eastman Kodak invented an organic EL device using a low molecular weight aromatic diamine and aluminum complex as an electroluminescent material in 1987 [App. Phys. Lett. 51, 913, 1987] .

The organic EL device is a device in which a pair of electrons and a hole are formed when an electric charge is applied to an organic film formed between an electron injecting electrode (cathode) and a hole injecting electrode (anode), and then fails with light emission. The device can be formed on a transparent flexible substrate such as plastic. Compared to a plasma display or an organic EL display, the device can operate at a lower voltage (not exceeding 10 volts (V)) at a relatively low power consumption, but with excellent color purity.

Since the organic electroluminescence (EL) device can display three colors (green, blue, and red), they are attracting attention as a next-generation full-color display device.

The process for manufacturing an organic EL device includes the following steps:

(1) First, an anode material is coated on a transparent substrate. ITO (indium tin oxide) is generally used as the anode material.

(2) A hole injection layer (HIL) is applied to the anode material. As the hole injection layer, beryllium bronze (CuPc) having a thickness of 10 nm (nano) to 30 nm is usually applied.

(3) After that, a hole transport layer (HIL) is introduced. As the hole transport layer, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) having a thickness of about 30 nm to 60 nm is deposited.

(4) Forming an organic light-emitting layer on the hole transport layer. Add dopants as needed. In the case of green electric field luminescence, ginseng (8-hydroxyquinoline) aluminum (Alq ₃ ) having a thickness of 30 nm to 60 nm is usually vapor-deposited as an organic light-emitting layer, and MQD (N-methylquinacridone) is usually used as the organic light-emitting layer. Dopant.

(5) Thereafter, an electron transport layer (ETL) and an electron injection layer (EIL) are sequentially coated on the organic light-emitting layer, or an electron injection/transport layer is formed. In the case of green electric field luminescence, since Alq _{3 of} (4) has excellent electron transport performance, it is not necessary to use an electron injection/transport layer.

(6) Thereafter, the cathode is coated and finally passivated.

A blue, green or red electric field illuminating device can be implemented depending on how the luminescent layer is formed in the structure. Meanwhile, when a conventional substance is used as a green electric field luminescent compound for realizing a green electric field light-emitting device, the life of the device is not long enough and the luminous efficiency is low.

In an organic EL device, the most important factor determining the luminous efficiency, lifetime, and the like is an electric field luminescent material. Some of the properties required for electroluminescent materials include high fluorescence quantum yield in solid state, high electron and hole mobility, poor decomposition during vacuum vapor deposition, and the formation of uniform and stable films.

Organic electroluminescent materials can be broadly classified into high molecular weight materials and low molecular weight materials. The low molecular weight material can be classified into a metal complex according to the molecular structure and a pure organic electroluminescent material containing no metal. The electroluminescent material comprises a chelate complex such as ginseng (8-hydroxyquinoline) aluminum, coumarin derivative, tetraphenylbutadiene derivative, bis(styryl extended aryl) derivative and Diazole derivatives. It has been reported that the use of such materials results in electric field illumination from the blue to red visible region, thereby enabling the realization of a full color display device.

In order to overcome the problems in the above conventional techniques, the inventors of the present invention have invented a novel electric field luminescent compound which can realize an organic electric field illuminating device having excellent luminescent efficiency and remarkably improved luminescent lifetime.

It is an object of the present invention to provide an organic electroluminescent compound having the framework structure to overcome the above problems while providing superior luminous efficiency and device life and having appropriate color coordinates than conventional host materials or dopant materials.

Another object of the present invention is to provide an organic electric field light-emitting device having high luminous efficiency and long life, which uses the organic electroluminescent compound as an electric field luminescent material.

Still another object of the present invention is to provide an organic electric field light-emitting device using the organic electroluminescent compound in an electric field light-emitting layer.

Still another object of the present invention is to provide an organic solar cell comprising the organic electroluminescent compound.

The present invention relates to an organic electroluminescent compound represented by the chemical formula (1) and an organic electric field light-emitting device comprising the same. The organic electroluminescent compound of the present invention has high luminous efficiency and excellent color purity and material life. Therefore, an OLED having a very excellent luminescence lifetime can be produced from the compound.

Wherein R ₁ to R ₁₀ independently represent hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60)aryl, (C3-C60)heteroaryl, N-morpholinyl, thio-N- Morpholinyl, 5- or 6-membered heterocycloalkyl, (C3-C60)cycloalkyl, tri(C1-C60)alkylnonane containing one or more heteroatoms selected from N, O, S and Si , bis(C1-C60)alkyl (C6-C60) aryl decyl, tris(C6-C60) arylalkyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60) olefin , (C2-C60)alkynyl, cyano, NR ₁₁ R ₁₂ , (C6-C60) aryl (C1-C60) alkyl, (C1-C60) alkoxy, (C1-C60) alkylthio (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitrate a base or a hydroxyl group, or a substituent selected from the following structures, but stipulates that R ₁ to R ₁₀ cannot be hydrogen at the same time:

R ₁₁ and R ₁₂ independently represent hydrogen, deuterium, (C1-C60)alkyl, (C3-C60)cycloalkyl, (C6-C60)aryl or (C3-C60)heteroaryl; R ₁₃ to R ₃₀ Independently represents hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60)aryl, (C3-C60)heteroaryl, N-morpholinyl, thio-N-morpholinyl, containing one or a plurality of 5-membered or 6-membered heterocycloalkyl groups selected from the group consisting of N, O, S and Si heteroatoms, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecanealkyl, and di(C1-C60) Alkyl (C6-C60) arylalkylene, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60) Alkynyl, cyano, (C1-C60)alkylamino, (C6-C60)arylamino, (C6-C60)aryl(C1-C60)alkyl, (C1-C60)alkoxy, (C1-C60) alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60 An arylcarbonyl group, a carboxyl group, a nitro group or a hydroxyl group, or R ₁₃ to R ₂₅ may be bonded to the phase via a (C3-C60)alkylene group or a (C3-C60)alkylene group with or without a fused ring. An ortho substituent to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; X and Y independently represent a chemical bond, -C(R ₃₁ )(R ₃₂ ) -, -N(R ₃₃ )-, -S-, -O-, -Si(R ₃₄ )(R ₃₅ )-, -P(R ₃₆ )-, -C(=O)-, -B(R ₃₇ ) -, -In(R ₃₈ )-, -Se-, -Ge(R ₃₉ )(R ₄₀ )-, -Sn(R ₄₁ )(R ₄₂ )-, -Ga(R ₄₃ )- or -( R ₄₄ )C=C(R ₄₅ )-; R ₃₁ to R ₄₅ independently represent hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60)aryl, (C3-C60)heteroaryl, N-morpholinyl, thio N-morpholinyl, 5- or 6-membered heterocycloalkyl, (C3-C60) cycloalkyl containing one or more heteroatoms selected from N, O, S and Si , tris(C1-C60)alkyldecanealkyl, di(C1-C60)alkyl(C6-C60)aryldecylalkyl, tris(C6-C60)aryldecylalkyl,adamantyl,(C7-C60) Bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, (C1-C60)alkylamino, (C6-C60)arylamine, (C6-C60)aryl (C1-C60)alkyl, (C1-C60)alkoxy, (C1-C60)alkylthio, (C6-C60)aryloxy, (C6-C60)arylthio, (C1-C60)alkane Oxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60)arylcarbonyl, carboxy, nitro or hydroxy, or R ₃₁ and R ₃₂ , R ₃₄ and R ₃₅ , R ₃₉ and R ₄₀ , R ₄₁ And R ₄₂ or R ₄₄ and R ₄₅ may be via (C3-C60)alkyl or (C3-C60) with or without a fused ring An alkenyl group is bonded to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; the alkyl group, the aryl group, the heteroaryl group, the heterocycloalkyl group, the cycloalkyl group, the trialkyl decane of R ₁ to R ₄₅ , dialkyl aryl decyl, triaryl decyl, adamantyl, bicycloalkyl, alkenyl, alkynyl, aralkyl, alkoxy, alkylthio, aryloxy, arylthio, alkane The arylamino group, the arylamino group, the alkoxycarbonyl group, the alkylcarbonyl group or the arylcarbonyl group may be further substituted with one or more substituents selected from the group consisting of hydrazine, halogen, with or without a halogen substituent (C1) -C60)alkyl, (C6-C60) aryl, (C3-C60)heteroaryl, N-morpholinyl, thio-N-morpholinyl with or without (C6-C60) aryl substituent a 5- or 6-membered heterocycloalkyl group containing one or more heteroatoms selected from N, O, S and Si, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecanealkyl, two (C1-C60)alkyl (C6-C60) aryldecyl, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, C2-C60) alkynyl, cyano, (C1-C60)alkylamino, (C6-C60)arylamino, (C6-C60)aryl(C1-C60)alkyl, (C 1-C60) alkoxy group, (C1-C60)alkylthio group, (C6-C60) aryloxy group, (C6-C60) arylthio group, (C1-C60) alkoxycarbonyl group, (C1-C60) An alkylcarbonyl group, a (C6-C60) arylcarbonyl group, a carboxyl group, a nitro group, and a hydroxyl group; and a represents an integer of 0 to 4.

Referring to the drawings, FIG. 1 is a schematic cross-sectional view of an OLED of the present invention, comprising a glass 1, a transparent electrode 2, a hole injection layer 3, a hole transport layer 4, an electroluminescent layer 5, an electron transport layer 6, and an electron injection layer. 7 and aluminum (Al) cathode 8.

The terms 'alkyl', 'alkoxy' and other substituents containing the 'alkyl' moiety as used herein include both straight-chain and branched-chain groups.

The term 'aryl' as used herein refers to an organic radical derived from the removal of one hydrogen atom from an aromatic hydrocarbon. Each ring suitably includes a monocyclic or fused ring system containing from 4 to 7 ring atoms, preferably from 5 to 6 ring atoms. Specific examples include, but are not limited to, phenyl, naphthyl, biphenyl, anthryl, fluorenyl, fluorenyl, phenanthryl, triphenylenyl, fluorenyl, fluorenyl, fluorenyl, fused tetraphenyl (naphthacenyl) and fluoranthenyl.

The term 'heteroaryl' as used herein refers to an aryl group containing from 1 to 4 heteroatoms selected from N, O, S and Si as an aromatic ring skeleton atom, and as a carbon atom of the remaining aromatic ring skeleton atom. . The heteroaryl group can be a 5- or 6-membered monocyclic heteroaryl group or a polycyclic heteroaryl group fused to one or more benzene rings and can be partially saturated. The heteroaryl group includes a divalent aryl group in which a hetero atom on the ring can be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt. Specific examples include, but are not limited to, monocyclic heteroaryl groups such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, iso Azolyl, Azolyl, Diazolyl, three Base, four Base, triazolyl, tetrazolyl, furazolyl, pyridyl, pyridyl Base, pyrimidinyl, oxime Polycyclic heteroaryl such as benzofuranyl, benzothienyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benziso Azolyl, benzo Azolyl, isodecyl, fluorenyl, oxazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, porphyrinyl, quinazolinyl, quin Base Lolinyl, oxazolyl, phenanthryl and benzodiazepine Benzodioxolyl or the like; and corresponding N-oxides (for example, pyridyl N-oxide, quinolinyl N-oxide) and quaternary salts.

The naphthyl group of the present invention may be 1-naphthyl or 2-naphthyl; the fluorenyl group may be 1-indenyl, 2-indenyl or 9-fluorenyl; and the mercapto may be 1-indenyl, 2 - anthracenyl, 3-indenyl, 4-indenyl or 9-fluorenyl.

The substituent of the present invention comprising a "(C1-C60)alkyl" moiety may contain from 1 to 60 carbon atoms, from 1 to 20 carbon atoms, or from 1 to 10 carbon atoms. The substituent containing the "(C6-C60) aryl" moiety may have 6 to 60 carbon atoms, 6 to 20 carbon atoms, or 6 to 12 carbon atoms. The substituent containing the "(C3-C60)heteroaryl" moiety may have 3 to 60 carbon atoms, 4 to 20 carbon atoms, or 4 to 12 carbon atoms. The substituent containing the "(C3-C60)cycloalkyl" moiety may have 3 to 60 carbon atoms, 3 to 20 carbon atoms, or 3 to 7 carbon atoms. The substituent containing the "(C2-C60)alkenyl or alkynyl" moiety may have 2 to 60 carbon atoms, 2 to 20 carbon atoms, or 2 to 10 carbon atoms.

The organic electroluminescent compound of the present invention can be represented by the chemical formula (2):

Wherein R ₁ to R ₈ are as defined in the formula (1); L ₁ and L ₂ independently represent a bond, (C1-C60)alkyloxy, (C1-C60)alkylthio, (C6-C60) Aryloxy, (C6-C60) extended arylthio, (C6-C60) extended aryl or (C3-C60) heteroaryl; Ar ₁ and Ar ₂ independently represent hydrogen, hydrazine, halogen, (C1- C60) alkyl, (C6-C60) aryl, (C3-C60)heteroaryl, N-morpholinyl, thio N-morpholinyl, containing one or more selected from the group consisting of N, O, S and Si 5 or 6 membered heterocycloalkyl, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecyl, di(C1-C60)alkyl(C6-C60)aryldecane , tris(C6-C60)arylalkylalkyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, NR ₁₁ R ₁₂ , (C6-C60) aryl (C1-C60) alkyl, (C1-C60) alkoxy, (C1-C60) alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio (C1-C60) alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60)arylcarbonyl, carboxy, nitro or hydroxy, or a substituent selected from the following structures:

R ₁₁ and R ₁₂ independently represent hydrogen, deuterium, (C1-C60)alkyl, (C3-C60)cycloalkyl, (C6-C60)aryl or (C3-C60)heteroaryl; R ₁₃ to R ₃₀ Independently represents hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60)aryl, (C3-C60)heteroaryl, N-morpholinyl, thio-N-morpholinyl, containing one or a plurality of 5-membered or 6-membered heterocycloalkyl groups selected from the group consisting of N, O, S and Si heteroatoms, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecanealkyl, and di(C1-C60) Alkyl (C6-C60) arylalkylene, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60) Alkynyl, cyano, (C1-C60)alkylamino, (C6-C60)arylamino, (C6-C60)aryl(C1-C60)alkyl, (C1-C60)alkoxy, (C1-C60) alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60 An arylcarbonyl group, a carboxyl group, a nitro group or a hydroxyl group, or R ₁₃ to R ₂₅ may be bonded individually via a (C3-C60)alkylene group or a (C3-C60)alkylene group with or without a fused ring. An alicyclic ring, or a monocyclic or polycyclic aromatic ring; X and Y independently represent a chemical bond, -C(R ₃₁ )(R ₃₂ )-, -N(R ₃₃ )-,- S-, -O-, -Si(R ₃₄ )(R ₃₅ )-, -P(R ₃₆ )-, -C(=O)-, -B(R ₃₇ )-, -In(R ₃₈ )- , -Se-, -Ge(R ₃₉ )(R ₄₀ )-, -Sn(R ₄₁ )(R ₄₂ )-, -Ga(R ₄₃ )- or -(R ₄₄ )C=C(R ₄₅ )- ; R ₃₁ to R ₄₅ independently represent hydrogen, hydrazine, halogen, (C1-C60)alkyl, (C6-C60) aryl, (C3-C60)heteroaryl, N-morpholinyl, thio-N-? a phenyl group, a 5- or 6-membered heterocycloalkyl group containing one or more heteroatoms selected from N, O, S and Si, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecanealkyl , (C1-C60)alkyl (C6-C60) aryldecyl, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl (C2-C60)alkynyl, cyano, (C1-C60)alkylamino, (C6-C60)arylamino, (C6-C60)aryl(C1-C60)alkyl, (C1- C60) alkoxy, (C1-C60)alkylthio, (C6-C60)aryloxy, (C6-C60)arylthio, (C1-C60)alkoxycarbonyl, (C1-C60)alkyl a carbonyl group, a (C6-C60) arylcarbonyl group, a carboxyl group, a nitro group or a hydroxyl group, or R ₃₁ and R ₃₂ , R ₃₄ and R ₃₅ , R ₃₉ and R ₄₀ , R ₄₁ and R ₄₂ or R ₄₄ and R ₄₅ may be via (C3-C60)alkylene or (C3-C60)alkylene linkage with or without a fused ring Form an alicyclic ring, or a monocyclic aromatic ring or rings; L ₁ and L ₂ of the heteroaryl group or an arylene or an arylene group; or Ar _1, Ar ₂ and R ₁₁ to R ₄₅ of the alkyl group, aryl group, Heteroaryl, heterocycloalkyl, cycloalkyl, trialkylalkyl, dialkylarylalkyl, triarylalkyl, adamantyl, bicycloalkyl, alkenyl, alkynyl, aralkyl, The alkoxy group, alkylthio group, aryloxy group, arylthio group, alkylamino group, arylamino group, alkoxycarbonyl group, alkylcarbonyl group or arylcarbonyl group may be further substituted by one or more selected from the group consisting of Base substitution: anthracene, halogen, (C1-C60)alkyl with or without a halogen substituent, (C6-C60) aryl, with or without (C6-C60) aryl substituent (C3-C60) Heteroaryl, N-morpholinyl, thio-N-morpholinyl, 5- or 6-membered heterocycloalkyl containing one or more heteroatoms selected from N, O, S and Si, (C3-C60 a cycloalkyl group, a tri(C1-C60)alkyldecyl group, a di(C1-C60)alkyl group (C6-C60)aryldecylalkyl group, a tris(C6-C60)aryldecylalkyl group, an adamantyl group, C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, (C1-C60)alkylamino, (C6-C60) Amino group, (C6-C60) aryl (C1-C60) alkyl, (C1-C60) alkoxy, (C1-C60) alkylthio, (C6-C60) aryloxy, (C6-C60 An arylthio group, a (C1-C60) alkoxycarbonyl group, a (C1-C60)alkylcarbonyl group, a (C6-C60)arylcarbonyl group, a carboxyl group, a nitro group and a hydroxyl group; and a represents an integer of 0 to 4.

Specifically, Ar ₁ , Ar ₂ , and R ₁ to R ₈ are each independently selected from, but not limited to, hydrogen, hydrazine, fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, n-butyl. , isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, decyl, dodecyl, hexadecane Base, benzyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butyl Oxyl, isobutoxy, tert-butoxy, n-pentyloxy, isopentyloxy, n-hexyloxy, n-heptyloxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptane Base, cyclooctyl, cyclodecyl, cyclodecyl, NN-morpholinyl, N-thio N-morpholinyl, morpholinyl, thiomorpholinyl, trimethyldecyl, triethyldecane , tripropyldecyl, tris(t-butyl)decyl, tert-butyldimethylalkyl, dimethylphenyldecyl, triphenyldecyl, bicyclo[2.2.1]heptyl , bicyclo [2.2.2] octyl, bicyclo [3.2.1] octyl, bicyclo [5.2.0] fluorenyl, bicyclo [4.2.2] 癸Bicyclo[2.2.2]octyl, 4-pentylbicyclo[2.2.2]octyl, vinyl, styryl, ethynyl, phenylethynyl, cyano, methylthio, phenoxy, benzene Thio, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, methylcarbonyl, ethylcarbonyl, benzylcarbonyl, phenylcarbonyl, carboxyl, nitro, hydroxy and the following structures:

Wherein R ₁₁ and R ₁₂ independently represent hydrogen, deuterium, (C1-C60)alkyl, (C3-C60)cycloalkyl, (C6-C60)aryl or (C3-C60)heteroaryl; R ₅₁ to R ₇₀ independently represents hydrogen, hydrazine, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl, N-morpholinyl, thio N-morpholinyl, containing 5 or 6 membered heterocycloalkyl, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecane, di(C1) of one or more heteroatoms selected from N, O, S and Si -C60)alkyl (C6-C60) aryldecyl, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2- C60) alkynyl, cyano, (C1-C60)alkylamino, (C6-C60) arylamino, (C6-C60) aryl (C1-C60) alkyl, (C1-C60) alkoxy (C1-C60)alkylthio, (C6-C60)aryloxy, (C6-C60)arylthio, (C1-C60)alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6 -C60) arylcarbonyl, carboxyl, nitro or hydroxy; L ₁ and L ₂ independently represent a chemical bond, (C6-C60) extended aryl or (C3-C60) heteroaryl; L ₁ and L ₂ The aryl or heteroaryl group may be further substituted with one or more substituents selected from the group consisting of hydrazine, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C3-C60)heteroaryl, N-morpholinyl, thio-N-morpholinyl, 5 or more heteroatoms selected from N, O, S and Si Or 6-membered heterocycloalkyl, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecane, bis(C1-C60)alkyl(C6-C60)aryldecyl,tri(C6) -C60) arylalkylalkyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, (C1-C60)alkylamino, (C6-C60) arylamino group, (C6-C60) aryl (C1-C60) alkyl group, (C1-C60) alkoxy group, (C1-C60) alkylthio group, (C6-C60) aryloxy group , (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro and hydroxy; X and Y are independent Represents -C(R ₃₁ )(R ₃₂ )-, -N(R ₃₃ )-, -S-, -O-, -Si(R ₃₄ )(R ₃₅ )-, -P(R ₃₆ )-,- C(=O)-, -B(R ₃₇ )-, -In(R ₃₈ )-, -Se-, -Ge(R ₃₉ )(R ₄₀ )-, -Sn(R ₄₁ )(R ₄₂ )- , -Ga(R ₄₃ )- or -(R ₄₄ )C=C(R ₄₅ )-; R ₃₁ to R ₄₅ independently represent hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60) aryl , (C3-C60)heteroaryl, N-morpholinyl, thio-N-morpholinyl, containing one or more selected from N, O, S and 5- or 6-membered heterocycloalkyl of a hetero atom of Si, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecane, bis(C1-C60)alkyl(C6-C60)aryl矽alkyl, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, (C1-C60 An alkylamino group, (C6-C60) arylamino group, (C6-C60) aryl (C1-C60) alkyl group, (C1-C60) alkoxy group, (C1-C60) alkylthio group, ( C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro or a hydroxyl group; or R ₃₁ and R ₃₂ , R ₃₄ and R ₃₅ , R ₃₉ and R ₄₀ , R ₄₁ and R ₄₂ or R ₄₄ and R ₄₅ may be via a (C3-C60) alkyl group with or without a fused ring Or (C3-C60) an alkenyl group to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; R ₁₁ , R ₁₂ , R ₅₁ to R ₇₀ and R ₃₁ to R ₄₅ of the alkyl group, aryl group ,heteroaryl,heterocycloalkyl,cycloalkyl,trialkyldecyl,dialkylaryldecyl,triaryldecyl,adamantyl,bicycloalkyl,alkenyl,alkynyl,alkylamine Base, arylamine, alkylthio, alkoxy, aryloxy or aryl The thio group may further be fluorene, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl, N-morpholinyl, thio N-morpholinyl, containing one Or a plurality of 5-membered or 6-membered heterocycloalkyl groups selected from heteroatoms of N, O and S, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecanealkyl, di(C1-C60) Alkyl (C6-C60) arylalkylene, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkyne , cyano, (C1-C60)alkylamino, (C6-C60)arylamino, (C6-C60)aryl(C1-C60)alkyl, (C1-C60)alkoxy, ( C1-C60) alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60) An arylcarbonyl group, a carboxyl group, a nitro group or a hydroxy group; and b represents an integer from 1 to 5; and c represents an integer from 1 to 4.

More specifically, Ar ₁ , Ar ₂ , and R ₁ to R _{8 are} independently selected from, but not limited to, the following structures:

In the chemical formula (2), L ₁ and L ₂ independently represent, but are not limited to, a chemical bond, a (C6-C60) extended aryl group selected from the following structures, or a hetero-aryl group:

Wherein R ₈₁ to R ₈₆ independently represent hydrogen, deuterium, halogen, (C1-C60)alkyl group having or not containing a halogen substituent, (C6-C60) aryl group, with or without (C6-C60) aryl group Substituted (C3-C60)heteroaryl, N-morpholinyl, thio-N-morpholinyl, 5- or 6-membered heteropoly containing one or more heteroatoms selected from N, O, S, and Si Cycloalkyl, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecyl, bis(C1-C60)alkyl(C6-C60)aryldecyl,tri(C6-C60)aryl矽alkyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, (C1-C60)alkylamino, (C6-C60) Arylamino, (C6-C60) aryl (C1-C60) alkyl, (C1-C60) alkoxy, (C1-C60) alkylthio, (C6-C60) aryloxy, (C6- C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60)arylcarbonyl, carbonyl, nitro or hydroxy.

The organic electroluminescent compound of the present invention can be more specifically illustrated by the following compounds, but is not limited thereto:

The organic electroluminescent compound of the present invention can be prepared according to the process exemplified in Reaction Scheme (1):

Wherein R ₁ to R ₈ , L ₁ , L ₂ , Ar ₁ and Ar ₂ are as defined in the chemical formula (2).

Further, the present invention provides an organic solar cell comprising one or more organic electroluminescent compounds represented by the chemical formula (1).

The present invention also provides an organic electric field light-emitting device comprising: a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode; wherein the organic layer comprises one or more chemical formulas (1) ) an organic electric field luminescent compound represented. The organic electroluminescent compound can be used as a host material or dopant for an electroluminescent layer.

The organic electric field illuminating device of the present invention is characterized in that the organic layer comprises an electric field illuminating layer, which contains one or more kinds of dopants or in addition to one or more organic electroluminescent compounds represented by the chemical formula (1) Body material. The dopant or host material to be applied to the organic electroluminescence device of the present invention is not particularly limited.

The dopant applied to the organic electroluminescence device of the present invention is preferably selected from the compounds represented by one of Chemical Formulas (3) to (6):

Wherein R ₁₀₁ to R ₁₀₄ independently represent hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60)aryl, (C4-C60)heteroaryl, containing one or more selected from N, O And a 5-membered or 6-membered heterocycloalkyl group of S, a (C3-C60) cycloalkyl group, a tri(C1-C60)alkyldecane group, and a di(C1-C60)alkyl group (C6-C60) Base alkyl, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, (C1- C60) alkylamino group, (C6-C60) arylamino group, (C6-C60) aryl (C1-C60) alkyl group, (C6-C60) aryloxy group, (C1-C60) alkoxy group, (C1-C60)alkylthio, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro Or a hydroxy group, or R ₁₀₁ to R ₁₀₄ may be bonded to an adjacent substituent via a (C3-C60)alkylene group or a (C3-C60)alkylene group with or without a fused ring to form an alicyclic ring, or a single a cyclic or polycyclic aromatic ring; and the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylalkyl, alkylalkyl group of R ₁₀₁ to R ₁₀₄ Alkoxy, aryloxy, arylthio, alkylamino Aryl group, or R ₁₀₁ to R ₁₀₄ via the alicyclic with or without a fused ring of (C3-C60) alkylene or (C3-C60) alkenylene group linking adjacent substituents to form the Or the monocyclic or polycyclic aromatic ring may be further substituted with one or more substituents selected from the group consisting of hydrazine, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C4-C60) a heteroaryl group, a 5- or 6-membered heterocycloalkyl group containing one or more heteroatoms selected from N, O and S, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecanealkyl , (C1-C60)alkyl (C6-C60) aryldecyl, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl (C2-C60)alkynyl, cyano, (C1-C60)alkylamino, (C6-C60)arylamino, (C6-C60)aryl(C1-C60)alkyl, (C6- C60) aryloxy, (C1-C60) alkoxy, (C1-C60)alkylthio, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60)alkyl a carbonyl group, a (C6-C60) arylcarbonyl group, a carboxyl group, a nitro group and a hydroxyl group;

Wherein Ar ₁₁ and Ar ₁₂ independently represent (C1-C60)alkyl, (C6-C60)aryl, (C4-C60)heteroaryl, (C6-C60)arylamine, (C1-C60)alkane Amino group, 5- or 6-membered heterocycloalkyl or (C3-C60)cycloalkyl containing one or more heteroatoms selected from N, O and S, or Ar ₁₁ and Ar ₁₂ may be via or not a (C3-C60)alkylene group or a (C3-C60)alkylene group containing a fused ring to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; when d is 1, Ar ₁₃ represents (C6) -C60) aryl, (C4-C60)heteroaryl or an aryl group having one of the following structures:

When d is 2, Ar ₁₃ represents a (C6-C60) extended aryl group, a (C4-C60) heteroaryl group or an extended aryl group having one of the following structures:

Ar ₂₁ and Ar ₂₂ independently represent (C6-C60) an aryl or (C4-C60) heteroaryl; R ₁₁₀ , R ₁₁₁ and R ₁₁₂ independently represent hydrogen, deuterium, (C1-C60) alkyl or (C6) -C60) aryl; e is an integer from 1 to 4, f is an integer of 0 or 1; and the alkyl, aryl, heteroaryl, arylamine, alkylamine, ring of Ar ₁₁ and Ar ₁₂ An alkyl or heterocycloalkyl group; the aryl, heteroaryl, aryl or heteroaryl group of Ar ₁₃ ; the aryl or heteroaryl group of Ar ₂₁ and Ar ₂₂ ; or R ₁₁₀ to R ₁₁₂ The alkyl or aryl group may be further substituted with one or more substituents selected from the group consisting of hydrazine, halogen, (C1-C60)alkyl, (C6-C60) aryl, (C4-C60)heteroaryl a 5- or 6-membered heterocycloalkyl group containing one or more heteroatoms selected from N, O and S, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecanealkyl, di(C1) -C60)alkyl (C6-C60) aryldecyl, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2- C60) alkynyl, cyano, (C1-C60)alkylamino, (C6-C60) arylamino, (C6-C60) aryl (C1-C60) alkyl, (C6-C60) aryloxy Base, (C1-C60) alkoxy, (C6-C60) arylthio, (C1-C60) alkane Thio group, (C1-C60) alkoxycarbonyl group, (C1-C60) alkylcarbonyl group, (C6-C60) arylcarbonyl group, carboxyl group, nitro group and hydroxyl group;

Chemical formula (6)

M ¹ L ¹⁰¹ L ¹⁰² L ¹⁰³

Wherein M ¹ is a metal selected from the group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 of the Periodic Table of Elements and Group 16; and the ligands L ¹⁰¹ , L ¹⁰² and L ¹⁰³ are independently selected from the following structures:

Wherein R ₂₀₁ to R ₂₀₃ independently represent hydrogen, deuterium, (C1-C60)alkyl group having or not containing a halogen substituent, (C6-C60) aryl group having or not containing a (C1-C60) alkyl substituent; Or halogen; R ₂₀₄ to R ₂₁₉ independently represent hydrogen, hydrazine, (C1-C60)alkyl, (C1-C30) alkoxy, (C3-C60)cycloalkyl, (C2-C30)alkenyl, ( C6-C60) aryl, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, SF ₅ , tri(C1-C30)alkyldecyl, di(C1 -C30)alkyl (C6-C30) arylalkyl, tris(C6-C30)aryldecyl, cyano or halogen, and the alkyl, cycloalkyl, alkenyl or aryl of R ₂₀₄ to R ₂₁₉ The group may be further substituted with one or more substituents selected from the group consisting of hydrazine, (C1-C60) alkyl, (C6-C60) aryl and halogen; R ₂₂₀ to R ₂₂₃ independently represent hydrogen, hydrazine, with or without halogen a (C1-C60) alkyl group of a substituent, or a (C6-C60) aryl group having or not containing a (C1-C60) alkyl substituent; R ₂₂₄ and R ₂₂₅ independently represent hydrogen, deuterium, (C1-C60) alkyl, (C6-C60) aryl or halogen, or R ₂₂₄ and R ₂₂₅ may or may not contain through rings fused (C3-C12) alkylene or (C3-C12) alkenylene group to form a linkage Ring, or a monocyclic aromatic ring or rings, and R ₂₂₄ and R ₂₂₅ of the alkyl or aryl group, R ₂₂₄ and R ₂₂₅ or fused rings via (C3-C12) alkylene or may not contain or (C3-C12) the alicyclic ring formed by the alkenyl chain linkage, or the monocyclic or polycyclic aromatic ring may further be subjected to one or more (C1-C60) alkane selected from the group consisting of a halogen substituent or a halogen substituent. a substituent of a (C1-C30) alkoxy group, a hydrazine, a halogen, a tri(C1-C30)alkyldecyl group, a tris(C6-C30)aryldecylalkyl group, and a (C6-C60)aryl group; ₂₂₆ represents (C1-C60)alkyl, (C6-C60)aryl, (C5-C60)heteroaryl or halogen; _R227 to _R229 independently represent hydrogen, deuterium, (C1-C60)alkyl, (C6 -C60) aryl or halogen, and the alkyl or aryl group of R ₂₂₆ to R ₂₂₉ may be further substituted by halogen or (C1-C60)alkyl substituent; and Q represents , or Wherein R ₃₀₁ to R ₃₁₂ independently represent hydrogen, hydrazine, (C1-C60)alkyl group having or not containing a halogen substituent, (C1-C30) alkoxy group, halogen, (C6-C60) aryl group, cyanide Or a (C5-C60)cycloalkyl group, or R ₃₀₁ to R ₃₁₂ may be bonded to an adjacent substituent via an alkyl or alkenyl group to form a (C5-C7) spiro ring or a (C5-C9) thick group. Ring-bonded, or R ₃₀₁ to R ₃₁₂ may be bonded to R ₂₀₇ or R ₂₀₈ individually via an alkyl or alkenyl group to form a (C5-C7) fused ring.

The dopant compound represented by one of Chemical Formula (3) to Chemical Formula (6) can be exemplified by the following compounds, but is not limited thereto.

The host compound to be applied to the organic electroluminescent compound of the present invention may be selected from the compounds represented by the chemical formula (7) or the chemical formula (8):

Chemical formula (7)

(Ar ₃₁ ) _g -L _{twenty one} -(Ar ₃₂ ) _h

Chemical formula (8)

(Ar ₃₃ ) _i -L _{twenty two} -(Ar ₃₄ ) _j

Wherein, L ₂₁ represents (C6-C60) an aryl group or a (C4-C60) heteroaryl group; L ₂₂ represents a fluorenyl group; and Ar ₃₁ to Ar _{34 are} independently selected from hydrogen, hydrazine, (C1-C60) alkyl group. (C1-C60) alkoxy, halogen, (C4-C60)heteroaryl, (C5-C60)cycloalkyl and (C6-C60)aryl; Ar ₃₁ to Ar ₃₄ of the cycloalkyl, aryl The base or heteroaryl group may be further substituted with one or more substituents selected from the group consisting of one or more (C1-C60) alkyl groups selected from the group consisting of hydrazine, with or without a halogen substituent, C1-C60) alkoxy, (C3-C60)cycloalkyl, halogen, cyano, tri(C1-C60)alkyldecyl, di(C1-C60)alkyl(C6-C60)aryldecyl And (C6-C60) aryl or (C4-C60)heteroaryl group as a substituent of the group consisting of tris(C6-C60)arylalkylalkyl; (C1-C60) alkane with or without a halogen substituent (C1-C60) alkoxy; (C3-C60)cycloalkyl; anthracene; halogen; cyano; tri(C1-C60)alkyldecane; di(C1-C60)alkyl (C6-C60 An aryl decyl group and a tris(C6-C60) aryl decyl group; and g, h, i and j independently represent an integer from 0 to 4.

The host material represented by the chemical formula (7) or the chemical formula (8) can be exemplified by an anthracene derivative represented by one of the chemical formulas (9) to (11) and a benzo[a]pyrene derivative:

Wherein R ₄₀₁ and R ₄₀₂ independently represent (C6-C60) aryl, (C4-C60)heteroaryl, 5-membered or 6-membered heterocycloalkane containing one or more heteroatoms selected from N, O and S Or a (C3-C60)cycloalkyl group; the aryl or heteroaryl group of R ₄₀₁ and R ₄₀₂ may be further substituted with one or more substituents selected from the group consisting of hydrazine, (C1-C60) Alkyl, halo(C1-C60)alkyl, (C1-C60)alkoxy, (C3-C60)cycloalkyl, (C6-C60)aryl, (C4-C60)heteroaryl, halogen, Cyano, tri(C1-C60)alkyldecyl, di(C1-C60)alkyl(C6-C60)aryldecyl and tris(C6-C60)aryldecyl; R ₄₀₃ to R ₄₀₆ independently Hydrogen, hydrazine, (C1-C60)alkyl, (C1-C60)alkoxy, halogen, (C4-C60)heteroaryl, (C5-C60)cycloalkyl or (C6-C60)aryl; R The heteroaryl, cycloalkyl or aryl group of ₄₀₃ to R ₄₀₆ may be further substituted with one or more substituents selected from the group consisting of (C1-C60)alkyl groups with or without a halogen substituent. (C1-C60) alkoxy, (C3-C60)cycloalkyl, anthracene, halogen, cyano, tri(C1-C60)alkyldecyl, di(C1-C60)alkyl (C6-C60) Arylalkylene and tris(C6-C60) Silicon alkyl group; G ₁ and G ₂ independently represent a chemical bond, or with or without one or more groups selected from (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60) aryl, ( a C4-C60) (C6-C60) extended aryl group of a heteroaryl group and a halogen substituent; and Ar ₄₁ and Ar ₄₂ independently represent an aryl group or a (C4-C60) heteroaryl group selected from the following structures;

The aryl or heteroaryl group of Ar ₄₁ and Ar ₄₂ may further be one or more selected from the group consisting of (C1-C60)alkyl, (C1-C60) alkoxy, (C6-C60) aryl and (C4- C60) a substituent substituted with a heteroaryl group; L ₃₁ represents a (C6-C60) extended aryl group, a (C4-C60) heteroaryl group or a group having the following structure;

The aryl or heteroaryl group of L ₃₁ may be one or more selected from the group consisting of (C1-C60)alkyl, (C1-C60) alkoxy, (C6-C60) aryl, (C4-C60) Substituted by a heteroaryl group and a halogen substituent; R ₄₁₁ , R ₄₁₂ , R ₄₁₃ and R ₄₁₄ independently represent hydrogen, deuterium, (C1-C60)alkyl or (C6-C60)aryl, or R ₄₁₁ , R ₄₁₂ , R ₄₁₃ and R ₄₁₄ may be bonded to an adjacent substituent via a (C3-C60)alkylene group or a (C3-C60)alkylene group with or without a fused ring to form an alicyclic ring, or a single ring or more. An aromatic ring of the ring; and R ₄₂₁ , R ₄₂₂ , R ₄₂₃ and R ₄₂₄ independently represent hydrogen, deuterium, (C1-C60) alkyl, (C1-C30) alkoxy, (C6-C60) aryl, (C4 -C60)heteroaryl or halogen, or R ₄₂₁ , R ₄₂₂ , R ₄₂₃ and R ₄₂₄ may be independently bonded via a (C3-C60)alkyl or (C3-C60)alkylene group with or without a fused ring Associated with adjacent substituents to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring.

The host compound represented by one of Chemical Formula (9) to Chemical Formula (11) can be exemplified by the following compounds, but is not limited thereto.

The organic electroluminescence device of the present invention may further comprise, in addition to the organic electroluminescent compound represented by the chemical formula (1), one or more compounds selected from the group consisting of arylamine compounds and styrylarylamine compounds. . Examples of the arylamine compound or the styrylarylamine compound include, but are not limited to, the compound represented by the chemical formula (12):

Wherein Ar ₅₁ and Ar ₅₂ independently represent (C1-C60)alkyl, (C6-C60)aryl, (C4-C60)heteroaryl, (C6-C60)arylamine, (C1-C60)alkane Amino group, N-morpholinyl group, thio N-morpholinyl group, 5- or 6-membered heterocycloalkyl or (C3-C60) ring containing one or more heteroatoms selected from N, O and S An alkyl group, or Ar ₅₁ and Ar ₅₂ may be bonded via an (C3-C60)alkylene group or a (C3-C60)alkylene group with or without a fused ring to form an alicyclic ring, or a monocyclic or polycyclic ring. An aromatic ring; the aryl, heteroaryl, arylamino or heterocycloalkyl group of Ar ₅₁ and Ar ₅₂ may be further substituted with one or more substituents selected from the group consisting of hydrazine, halogen, ( C1-C60)alkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, (C6-C60)aryl, (C4-C60)heteroaryl, containing one or more selected from N, O And a 5-membered or 6-membered heterocycloalkyl group of S, a (C3-C60) cycloalkyl group, a tri(C1-C60)alkyldecane group, and a di(C1-C60)alkyl group (C6-C60) Base alkyl, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C1-C60)alkoxy, (C1-C60)alkylthio, cyano, C1-C60) alkylamino group, (C6-C60) arylamine group, ( C6-C60) aryl (C1-C60) alkyl, (C6-C60) aryloxy, (C6-C60) arylthio, (C6-C60) arylcarbonyl, (C1-C60) alkoxycarbonyl , (C1-C60)alkylcarbonyl, carboxyl, nitro and hydroxy; Ar ₅₃ represents (C6-C60) aryl, (C5-C60)heteroaryl or (C6-C60) arylamine; Ar ₅₃ The aryl, heteroaryl or arylamine group may be further substituted with one or more substituents selected from the group consisting of hydrazine, halogen, (C1-C60)alkyl, (C6-C60) aryl, (C4- C60) heteroaryl, 5- or 6-membered heterocycloalkyl, (C3-C60)cycloalkyl, tri(C1-C60)alkylnonane containing one or more heteroatoms selected from N, O and S , bis(C1-C60)alkyl (C6-C60) aryl decyl, tris(C6-C60) arylalkyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60) olefin , (C2-C60)alkynyl, (C1-C60)alkoxy, (C1-C60)alkylthio, cyano, (C1-C60)alkylamino, (C6-C60) arylamine (C6-C60) aryl (C1-C60) alkyl, (C6-C60) aryloxy, (C6-C60) arylthio, (C6-C60) arylcarbonyl, (C1-C60) alkoxy a carbonyl group, a (C1-C60)alkylcarbonyl group, a carboxyl group, a nitro group, and a hydroxyl group; and an integer of the k series 1 to 4.

The arylamine compound or the styrylarylamine compound can be more specifically illustrated by the following compounds, but is not limited thereto.

In the organic electric field light-emitting device of the present invention, the organic layer may further comprise, in addition to the organic electroluminescent compound represented by the chemical formula (1), one or more metals selected from the group consisting of: Periodic Table of Elements Group 1 organometallic, Group 2 organometallic, transition metal of the 4th and 5th cycles, lanthanide metal and d-transition element. The organic layer may include an electric field luminescent layer and a charge generating layer.

The present invention can realize an organic electric field light-emitting device having a pixel structure of an independent light-emitting mode, comprising an organic electric field light-emitting device containing the following compounds: an organic electroluminescent compound represented by the chemical formula (1) as a sub-pixel; and one or more simultaneous Parallel patterned sub-pixels comprising one or more metal compounds selected from the group consisting of Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au And Ag.

In the organic electroluminescence device of the present invention, one or more layers (hereinafter referred to as "surface layer") are preferably selected from the group consisting of a chalcogenide layer, a metal halide layer and a metal oxide layer. On the inner surface of at least one side of the pair of electrodes. Specifically, it is preferable to dispose a chalcogenide compound layer of lanthanum with aluminum metal (including an oxide) on the anode surface of the EL medium layer, and to provide a metal halide layer or a metal oxide layer at the cathode of the EL medium layer. On the surface. Thereby, operational stability can be obtained.

Examples of the chalcogen compound preferably include SiOx (1≦x≦2), AlOx (1≦x≦1.5), SiON, SiAlON, and the like. Examples of the metal halide preferably include LiF, MgF ₂ , CaF ₂ , a fluoride of a rare earth metal, and the like. Examples of the metal oxide preferably include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO, and the like.

In the organic electric field light-emitting device of the present invention, it is preferable that a mixed region of the electron transporting compound and the reducing dopant or a mixed region of the hole transporting compound and the oxidizing dopant is provided in the electrode pair manufactured as described above. At least one surface. Thereby, the electron transporting compound is reduced to an anion, thereby causing electrons to be injected and transported from the mixed region to the EL medium. In addition, since the hole transporting compound is oxidized to form a cation, the hole is caused to be injected and transported from the mixed region to the EL medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof.

The organic electroluminescent compound of the present invention has high luminous efficiency, excellent color purity, and material lifetime performance, so that an organic light-emitting diode (OLED) having a high operational life can be produced from the compound.

Best case

The present invention is further illustrated by reference to a representative compound of the present invention to further illustrate the luminescent properties of the organic electroluminescent compound of the present invention, the process for preparing the compound, and the device produced by the following examples, which are provided as illustrative examples. The invention is not intended to be limited in any way.

[Preparation example] [Preparation Example 1] Preparation of Compound (7)

Preparation of Compound (A)

2-Bromobenzaldehyde (20.0 g (g), 108.09 mmol (mmol)), 1-naphthalene boronic acid (22.31 g, 129.72 mmol), tetrakis(triphenylphosphine)palladium(0) (6.24 g, 5.4) Methyl) and calcium carbonate (60.27 g, 432.36 mmol) were charged into the reactor. After adding a toluene solvent (1000 ml (mL)), the mixture was stirred. Thereafter, ethanol (300 mL) and water (200 mL) were sequentially added, and the resulting mixture was stirred under reflux at 120 ° C for 15 hours. When the reaction was completed, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (500 mL). The organic extract was washed with brine and dried over anhydrous magnesium sulfate. After filtration through cerium oxide, the filtrate was evaporated to remove the organic solvent. The residual liquid was recrystallized from dichloromethane (100 mL) and n-hexane (500 mL) to afford Compound A (15.06 g, 60%).

Preparation of Compound (B)

n-Butyllithium (31 mL, 77.49 mmol) was slowly added dropwise to diisopropylamine (11.83 mL, 83.95 mmol) at 0 °C. The reaction mixture was then cooled to -78.degree. C. and trimethyl succinyl diazomethane (12.33 mL, 77.49 mmol) was added dropwise over 30 min. After stirring for 30 minutes, Compound A (15.0 g, 64.58 mmol) diluted THF (50 mL) was slowly added dropwise. After 3 hours, water was added to terminate the reaction, and the mixture was extracted with ethyl acetate (200 mL). The obtained organic extract was purified by column chromatography using ethyl acetate / n-hexane = 1/10 to afford Compound B (10.5 g, 71%).

Preparation of compound (C)

Compound B (10.0 g, 43.80 mmol), platinum chloride (PtCl ₂ ) (582 mg, 2.19 mmol) and toluene solvent (200 mL) were charged to the reactor, and the mixture was stirred under reflux at 80 ° C for 24 hours. When the reaction is complete, water is added to terminate the reaction. The mixture was then extracted with dichloromethane (300 mL) to separate organic layers. The obtained organic layer was dried over anhydrous magnesium sulfate and filtered over EtOAc. After evaporating under reduced pressure, the residue was purified mjjjjlilililililililili

Preparation of Compound (D)

Compound C (9.0 g, 39.42 mmol) was dissolved in chloroform solvent (300 mL), and bromine (4.45 mL, 86.72 mmol) was slowly added dropwise to the solution. After 5 hours, the reaction was quenched by the addition of water and the mixture was extracted with dichloromethane. The obtained organic layer was dried over anhydrous magnesium sulfate and filtered through EtOAc. The organic solvent was removed by distillation under reduced pressure, and residue was crystallised from dichloromethane (100mL) and methanol (300mL) to afford Compound D (12.94 g, 85%).

Preparation of compound (7)

Compound D (2.0g, 4.13mmol), phenylboronic acid (1.3g, 10.33mmol) and _{Pd (PPh 3) 4 (0.6g} , 0.41mmol) was dissolved in toluene (100 mL) and ethanol (50mL) in. After a 2 M aqueous sodium carbonate solution (50 mL) was added, the mixture was refluxed at 120 ° C for 4 hours. Thereafter, the reaction mixture was cooled to 25 ° C, and the reaction was terminated by adding distilled water (200 mL). The mixture was extracted with ethyl acetate (150 mL) and evaporated. The title compound (Compound 7) (1.6 g, 3.33 mmol) was obtained.

Preparation 2 Preparation of Compound (147)

Preparation of Compound (147)

Compound D (10.0 g, 25.9 mmol), diphenylamine (10.96 g, 64.75 mmol), palladium (II) acetate (290 mg (mg), 1.29 mmol), tri-tert-butylphosphine under a nitrogen atmosphere (0.64 mL, 2.59 mmol) and sodium tributoxide (7.47 g, 77.7 mmol) were charged into the reactor, and toluene solvent (200 mL) was added. The mixture was stirred under reflux at 120 ° C for 3 hours. When the reaction was completed, the reaction was quenched by the addition of water and the mixture was extracted with dichloromethane (300 mL). The obtained organic layer was dried over anhydrous magnesium sulfate and filtered through EtOAc. The organic layer was evaporated under reduced pressure and dichloromethane was evaporated, mjjjjjjjj

The organic electroluminescent compound (Compound 1 to Compound 532) was prepared in the same manner as in Preparation Example 1 and Preparation Example 2. The ¹ H NMR and MS/FAB data of the prepared compound are shown in Table 1.

[Example 1] Manufacture of OLED using organic electroluminescent compound of the present invention

An OLED device is fabricated using the electroluminescent material of the present invention.

First, the transparent electrode (2) ITO film (15 Ω / □) obtained from OLED glass (1) (manufactured by Samsung Corning) was washed with trichloroethylene, acetone, ethanol, and distilled water in sequence, and stored. Used in isopropanol.

Then, the ITO substrate was assembled in a substrate holder of a vacuum vapor deposition apparatus, and 4,4',4"-parameter (N,N-(2-naphthyl)-phenylamino)triphenylamine (2- TNATA) (having the structure shown below) is placed in a chamber of the vacuum vapor deposition apparatus, and then ventilated in the chamber to reach a vacuum of 10 ^-6 torr. A current is applied to the chamber to volatilize 2-TNATA, Thereby, a hole injection layer (3) having a thickness of 60 nm was vapor-deposited on the ITO substrate.

Next, N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) (the structure of which is shown below) is filled into the vacuum vapor deposition apparatus. In another chamber, a current is applied to the chamber to volatilize NPB, thereby depositing a hole transport layer (4) having a thickness of 20 nm on the hole injection layer.

After the hole injection layer and the hole transport layer are formed, the electric field light-emitting layer is vapor-deposited in the following manner. The compound of the present invention (e.g., compound 17) is filled in a chamber of a vacuum vapor deposition apparatus as an electroluminescent material, and DSA-Ph (the structure of which is shown below) is filled into another chamber. The two chambers are simultaneously heated for vapor deposition at a deposition rate of 2% by weight to 5% by weight of DSA-Ph to vapor-deposit an electroluminescent layer (5) having a thickness of 30 nm on the hole transport layer.

Next, vapor-deposited ginseng (8-hydroxyquinoline) aluminum (III) (Alq) (structure is shown below) as an electron transport layer (6) having a thickness of 20 nm, and vapor deposition of lithium quinolate (Liq) (The structure is as follows) as an electron injecting layer (7) having a thickness of 1 nm to 2 nm. Then, another vacuum vapor deposition apparatus was used to vapor-deposit the aluminum cathode (8) having a thickness of 150 nm to fabricate an OLED.

Each of the materials used to fabricate the electroluminescent material as an OLED was purified by vacuum sublimation at a pressure of 10 ^-6 torr before use.

[Comparative Example 1] Manufacture of OLED using a conventional EL material

After the hole injection layer (3) and the hole transport layer (4) are formed in the same manner as described in Embodiment 1, dinaphthyl ruthenium (DNA) is filled into another chamber of the vacuum vapor deposition apparatus, and The DSA-Ph was filled into yet another chamber as in Example 1. Then, an electric field light-emitting layer (5) having a thickness of 30 nm was vapor-deposited on the hole transport layer at a vapor deposition rate of 100:3.

Subsequently, the electron transport layer (6) and the electron injection layer (7) were vapor-deposited in the same manner as described in Example 1, and then an aluminum cathode (8) having a thickness of 150 nm was vapor-deposited by another vacuum vapor deposition apparatus. And the OLED is manufactured.

The luminous efficiency of the OLED comprising the organic electroluminescent compound of the present invention (Example 1) or the conventional EL compound (Comparative Example 1) was measured at 5,000 candelas (cd) per square meter (m ² ), and the results are shown in Table 2.

As can be seen from Table 2, a blue electric field light-emitting device (DSA-Ph is usually doped to the organic electroluminescent compound of the present invention) to which the material of the present invention is applied is used as compared with a device using DNA as a conventional electroluminescent material (Comparative Example 1). It shows considerable luminous efficiency but far superior color purity.

[Example 2] Manufacture of OLED using organic electroluminescent compound of the present invention

After forming the hole injection layer and the hole transport layer in the same manner as described in Embodiment 1, the compound of the present invention (such as Compound 17) is filled into a chamber of the vacuum vapor deposition apparatus as an electric field luminescent material, and Compound E (having the structure shown below) was filled into another chamber. Then, the two materials are volatilized at different rates to perform doping at a concentration of 2% by weight to 5% by weight (based on the host material), thereby vapor-depositing an electric field of 30 nm on the hole transport layer. Floor.

Next, an electron transport layer and an electron injection layer were vapor-deposited in the same manner as described in Example 1, and then an aluminum cathode having a thickness of 150 nm was vapor-deposited by another vacuum vapor deposition apparatus to fabricate an OLED.

[Comparative Example 2] Manufacture of OLED using a conventional EL material

After forming the hole injection layer and the hole transport layer by the same method as described in Example 1, ginseng (8-hydroxyquinoline) aluminum (III) (Alq) was filled as an electric field luminescent host material into the vacuum vapor deposition apparatus. In another chamber, coumarin 545T (C545T) (structure shown below) was filled into yet another chamber of the vacuum vapor deposition apparatus. Then, the two materials are volatilized at different rates to effect doping, thereby vapor-depositing an electric field luminescent layer having a thickness of 30 nm on the hole transport layer. The doping concentration is preferably from 1% by weight to 3% by weight (based on Alq).

Subsequently, an electron transport layer and an electron injection layer were vapor-deposited in the same manner as described in Example 1, and then an aluminum cathode having a thickness of 150 nm was vapor-deposited by another vacuum vapor deposition apparatus to fabricate an OLED.

The luminous efficiency of the OLED comprising the organic electroluminescent compound of Example (Example 2) or the conventional EL compound (Comparative Example 2) was measured at 5,000 cd/m ² , and the results are shown in Table 3.

As can be seen from Table 3, the green field illuminating device to which the inventive material is applied, particularly the device using the doping concentration of 3.0% compound E to dope the organic electroluminescent compound (compound 214) of the present invention, has higher luminous efficiency than using Alq: C545T. The conventional device (Comparative Example 2) has twice the luminous efficiency.

[Example 3] Manufacture of OLED using organic electroluminescent compound of the present invention

After forming the hole injection layer and the hole transport layer by the same method as described in Embodiment 1, the compound of the present invention (such as Compound 41) is filled into a chamber of the vacuum vapor deposition apparatus as an electric field luminescent material, and An electric field luminescent dopant such as compound D-4 is packed into another chamber. Then, the two materials were volatilized at different rates and doped at a concentration of 8 wt%, whereby an electric field light-emitting layer (5) having a thickness of 30 nm was vapor-deposited on the hole transport layer.

Next, vapor-deposited ginseng (8-hydroxyquinoline) aluminum (III) (Alq) (structure is shown below) as an electron transport layer (6) having a thickness of 20 nm, and vapor deposition of lithium quinolate (Liq) (The structure is as follows) as an electron injecting layer (7) having a thickness of 1 nm to 2 nm. Then, another vacuum vapor deposition apparatus was used to vapor-deposit the aluminum cathode (8) having a thickness of 150 nm to fabricate an OLED.

Each of the materials used to fabricate the electroluminescent material as an OLED was purified by vacuum sublimation at a pressure of 10 ^-6 torr before use.

[Comparative Example 3] Manufacture of OLED using conventional EL material

After forming the hole injection layer and the hole transport layer by the same method as described in Example 3, 4,4'-N,N'-dicarbazole-biphenyl (CBP) was filled into the vacuum as an electric field luminescent host material. In another chamber of the vapor deposition apparatus, an electric field luminescent dopant such as compound D-4 is filled into another chamber of the vacuum vapor deposition apparatus. Then, the two materials are volatilized at different rates to effect doping, thereby vapor-depositing the electroluminescent layer (5) having a thickness of 30 nm on the hole transport layer. The doping concentration is preferably 8% by weight (based on CBP).

Subsequently, bis(2-methyl-8-hydroxyquinoline) (p-phenylphenol) aluminum (III) (BAlq) having a thickness of 10 nm was vapor-deposited on the electroluminescent layer as a hole barrier layer, gas phase A ginseng (8-hydroxyquinoline) aluminum (III) (Alq) having a thickness of 20 nm was deposited as an electron transport layer, followed by vapor deposition of lithium quinolate (Liq) having a thickness of 1 nm to 2 nm as an electron injection layer (7). ). An OLED was then fabricated by vapor deposition of an aluminum cathode having a thickness of 150 nm using another vacuum vapor deposition apparatus.

The results of the luminous efficiency of the OLED comprising the organic electroluminescent compound of Example (Example 3) or the conventional EL compound (Comparative Example 3) are shown in Table 4.

As can be seen from Table 4, the apparatus using the host material of the present invention but not including the hole barrier layer has an emission efficiency comparable to that of a device using CBP as a conventional phosphorescent host material and a lower (reduced 0.8-1.2 v) operating voltage. . Therefore, the power consumption of the OLED can be significantly reduced.

[Example 4] Manufacture of OLED using organic electroluminescent compound of the present invention

After forming the hole injection layer and the hole transport layer by the same method as described in Example 1, the ruthenium-type host material compound (compound H-29) is filled into a chamber of the vacuum vapor deposition apparatus as a host material, and The compound (147) of the present invention is filled into another chamber as a dopant. Then, the two materials are volatilized at different rates, and doped at a concentration of 3% by weight (based on the host material), thereby vapor-depositing an electric field luminescent layer having a thickness of 30 nm on the hole transport layer (5) .

Next, the electron transport layer and the electron injection layer were vapor-deposited in the same manner as described in Example 1, and another vacuum vapor deposition apparatus was used to vapor-deposit an aluminum cathode having a thickness of 150 nm to fabricate an OLED.

[Comparative Example 4] Manufacture of OLED using conventional EL material

After forming the hole injection layer and the hole transport layer in the same manner as described in Example 4, dinaphthyl fluorene (DNA) is filled as an electric field luminescent host material into another chamber of the vacuum vapor deposition apparatus, and The crucible is filled into another small chamber. Then, the two materials are volatilized at different rates to achieve doping, and an electric field luminescent layer having a thickness of 30 nm is vapor-deposited on the hole transport layer at a doping concentration of 3% by weight (based on the host material). ).

Subsequently, an electron transport layer and an electron injection layer were vapor-deposited in the same manner as described in Example 1, and then an aluminum cathode having a thickness of 150 nm was vapor-deposited by another vacuum vapor deposition apparatus to fabricate an OLED.

The results of the luminous efficiency of the OLED comprising the organic electroluminescent compound of Example (Example 4) or the conventional EL compound (Comparative Example 4) are shown in Table 5.

As can be seen from Table 5, the device which was doped with the compound (H-73) and was doped with 3% by weight of the compound (183) exhibited the highest luminous efficiency.

It is apparent from the experimental results that the organic electroluminescent compound of the present invention can be used as a highly efficient blue, green or red electric field luminescent material. Since the compound improves both color purity and luminous efficiency, an OLED having excellent performance can be produced from the electroluminescent material of the present invention.

1‧‧‧glass

2‧‧‧Transparent electrode

3‧‧‧ hole injection layer

4‧‧‧ hole transport layer

5‧‧‧Electroluminescent layer

6‧‧‧Electronic transport layer

7‧‧‧Electronic injection layer

8‧‧‧Aluminum cathode

Figure 1 is a schematic cross-sectional view of an OLED.

1. . . glass

2. . . Transparent electrode

3. . . Hole injection layer

4. . . Hole transport layer

5. . . Electric field luminescent layer

6. . . Electronic transport layer

7. . . Electron injection layer

8. . . Aluminum cathode

Claims (8)

An organic electroluminescent compound represented by the chemical formula (2): Wherein, L ₁ and L ₂ independently represent a chemical bond, (C1-C60)alkyloxy, (C1-C60)alkylthio, (C6-C60) extended aryloxy, (C6-C60) extended arylthio (C6-C60) aryl or (C3-C60) heteroaryl; Ar ₁ and Ar ₂ independently represent hydrogen, deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, C3-C60) heteroaryl, N-morpholinyl, thio N-morpholinyl, 5- or 6-membered heterocycloalkyl containing one or more heteroatoms selected from N, O, S and Si, (C3-C60) cycloalkyl, tri(C1-C60)alkyldecyl, di(C1-C60)alkyl(C6-C60)aryldecyl,tris(C6-C60)aryldecyl,gold Alkyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, NR ₁₁ R ₁₂ , (C6-C60) aryl (C1-C60)alkyl (C1-C60) alkoxy group, (C1-C60)alkylthio group, (C6-C60) aryloxy group, (C6-C60) arylthio group, (C1-C60) alkoxycarbonyl group, (C1- C60) an alkylcarbonyl group, a (C6-C60) arylcarbonyl group, a carboxyl group, a nitro group or a hydroxyl group, or a substituent selected from the following structures: R ₁ to R ₈ independently represent hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60)aryl, (C3-C60)heteroaryl, N-morpholinyl, thio-N-morpholine a 5- or 6-membered heterocycloalkyl group having one or more heteroatoms selected from N, O, S and Si, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecane, Di(C1-C60)alkyl (C6-C60) arylalkyl, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60) alkynyl, cyano, NR ₁₁ R ₁₂ , (C6-C60) aryl (C1-C60) alkyl, (C1-C60) alkoxy, (C1-C60)alkylthio, C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro or a hydroxyl group, or a substituent selected from the following structures: R ₁₁ and R ₁₂ independently represent hydrogen, deuterium, (C1-C60)alkyl, (C3-C60)cycloalkyl, (C6-C60)aryl or (C3-C60)heteroaryl; R ₁₃ to R ₃₀ Independently represents hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60)aryl, (C3-C60)heteroaryl, N-morpholinyl, thio-N-morpholinyl, containing one or a plurality of 5-membered or 6-membered heterocycloalkyl groups selected from the group consisting of N, O, S and Si heteroatoms, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecanealkyl, and di(C1-C60) Alkyl (C6-C60) arylalkylene, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60) Alkynyl, cyano, (C1-C60)alkylamino, (C6-C60)arylamino, (C6-C60)aryl(C1-C60)alkyl, (C1-C60)alkoxy, (C1-C60) alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60 An arylcarbonyl group, a carboxyl group, a nitro group or a hydroxyl group, or R ₁₃ to R ₂₅ may be bonded to the phase via a (C3-C60)alkylene group or a (C3-C60)alkylene group with or without a fused ring. An ortho substituent to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; X and Y independently represent a chemical bond, -C(R ₃₁ )(R ₃₂ ) -, -N(R ₃₃ )-, -S-, -O-, -Si(R ₃₄ )(R ₃₅ )-, -P(R ₃₆ )-, -C(=O)-, -B(R ₃₇ ) -, -In(R ₃₈ )-, -Se-, -Ge(R ₃₉ )(R ₄₀ )-, -Sn(R ₄₁ )(R ₄₂ )-, -Ga(R ₄₃ )- or -( R ₄₄ )C=C(R ₄₅ )-; R ₃₁ to R ₄₅ independently represent hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60)aryl, (C3-C60)heteroaryl, N-morpholinyl, thio N-morpholinyl, 5- or 6-membered heterocycloalkyl, (C3-C60) cycloalkyl containing one or more heteroatoms selected from N, O, S and Si , tris(C1-C60)alkyldecyl, di(C1-C60)alkyl(C6-C60)aryldecyl,tris(C6-C60)aryldecyl,adamantyl,(C7-C60) Bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, (C1-C60)alkylamino, (C6-C60)arylamine, (C6-C60)aryl (C1-C60)alkyl, (C1-C60)alkoxy, (C1-C60)alkylthio, (C6-C60)aryloxy, (C6-C60)arylthio, (C1-C60)alkane Oxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60)arylcarbonyl, carboxy, nitro or hydroxy, or R ₃₁ and R ₃₂ , R ₃₄ and R ₃₅ , R ₃₉ and R ₄₀ , R ₄₁ And R ₄₂ or R ₄₄ and R ₄₅ may be via (C3-C60) alkyl or (C3-C60) with or without a fused ring An alkenyl group bonded to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; an extended aryl or heteroaryl group of L ₁ and L ₂ ; or Ar ₁ , Ar ₂ and R ₁₁ to R ₄₅ The alkyl group, the aryl group, the heteroaryl group, the heterocycloalkyl group, the cycloalkyl group, the trialkyl decyl group, the dialkyl aryl decyl group, the triaryl decyl group, the adamantyl group, the bicycloalkyl group, the alkenyl group, An alkynyl group, an aralkyl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, an alkylamino group, an arylamino group, an alkoxycarbonyl group, an alkylcarbonyl group or an arylcarbonyl group may be further subjected to one or Substituted by a plurality of substituents selected from the group consisting of hydrazine, halogen, (C1-C60)alkyl with or without a halogen substituent, (C6-C60) aryl, with or without (C6-C60) aryl substitution a 5- or 6-membered heterocyclic ring containing (C3-C60)heteroaryl, N-morpholinyl, thio-N-morpholinyl, containing one or more heteroatoms selected from N, O, S and Si Alkyl, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecyl, di(C1-C60)alkyl(C6-C60)aryldecyl,tri(C6-C60)aryldecane Alkyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, (C1-C60) alkane Amine, (C6-C60) arylamine, (C6-C60) aryl (C1-C60) alkyl, (C1-C60) alkoxy, (C1-C60) alkylthio, (C6-C60 An aryloxy group, (C6-C60) arylthio group, (C1-C60) alkoxycarbonyl group, (C1-C60)alkylcarbonyl group, (C6-C60) arylcarbonyl group, carboxyl group, nitro group and hydroxyl group; An integer representing from 0 to 4; and a limitation that if Ar ₁ is a (C6-C60) aryl group, NR ₁₁ R ₁₂ or a carbazolyl group, L _{1 is} not a chemical bond or a (C6-C60) extended aryl group; Ar ₂ is (C6-C60) aryl, NR ₁₁ R ₁₂ or carbazolyl, then L _{2 is} not a chemical bond or (C6-C60) extended aryl; and R ₁ and R ₂ cannot be hydrogen at the same time. An organic electric field illuminating device comprising: a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode; wherein the organic layer comprises an organic electric field of claim 1 a luminescent compound; and one or more dopants selected from the group consisting of compounds represented by one of Chemical Formulas (3) to (6): Wherein R ₁₀₁ to R ₁₀₄ independently represent hydrogen, deuterium, halogen, (C1-C60)alkyl, (C6-C60)aryl, (C4-C60)heteroaryl, containing one or more selected from N, O And a 5-membered or 6-membered heterocycloalkyl group of S, a (C3-C60) cycloalkyl group, a tri(C1-C60)alkyldecane group, and a di(C1-C60)alkyl group (C6-C60) Base alkyl, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, (C1- C60) alkylamino group, (C6-C60) arylamino group, (C6-C60) aryl (C1-C60) alkyl group, (C6-C60) aryloxy group, (C1-C60) alkoxy group, (C1-C60)alkylthio, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro Or a hydroxy group, or R ₁₀₁ to R ₁₀₄ may be bonded to an adjacent substituent via a (C3-C60)alkylene group or a (C3-C60)alkylene group with or without a fused ring to form an alicyclic ring, or a single a cyclic or polycyclic aromatic ring; and the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylalkyl, alkylalkyl group of R ₁₀₁ to R ₁₀₄ Alkoxy, aryloxy, arylthio, alkylamino An arylamine group, or an alicyclic ring formed by linking an alkyl group having a condensed ring (C3-C60) alkyl group or (C3-C60) an extended alkenyl group to an adjacent substituent, or the monocyclic ring Or a polycyclic aromatic ring may be further substituted with one or more substituents selected from the group consisting of hydrazine, halogen, (C1-C60)alkyl, (C6-C60) aryl, (C4-C60)heteroaryl, 5- or 6-membered heterocycloalkyl, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecane, di(C1-) containing one or more heteroatoms selected from N, O and S C60) alkyl (C6-C60) aryldecyl, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60 Alkynyl, cyano, (C1-C60)alkylamino, (C6-C60) arylamino, (C6-C60) aryl (C1-C60) alkyl, (C6-C60) aryloxy (C1-C60) alkoxy, (C1-C60)alkylthio, (C6-C60)arylthio, (C1-C60)alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6- C60) an arylcarbonyl group, a carboxyl group, a nitro group and a hydroxyl group; Wherein Ar ₁₁ and Ar ₁₂ independently represent (C1-C60)alkyl, (C6-C60)aryl, (C4-C60)heteroaryl, (C6-C60)arylamine, (C1-C60)alkane Amino group, 5- or 6-membered heterocycloalkyl or (C3-C60)cycloalkyl containing one or more heteroatoms selected from N, O and S, or Ar ₁₁ and Ar ₁₂ may be via or not a (C3-C60)alkylene group or a (C3-C60)alkylene group containing a fused ring to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; when d is 1, Ar ₁₃ represents (C6) -C60) aryl, (C4-C60)heteroaryl or an aryl group having one of the following structures: When d is 2, Ar ₁₃ represents a (C6-C60) extended aryl group, a (C4-C60) heteroaryl group or an extended aryl group having one of the following structures: Ar ₂₁ and Ar ₂₂ independently represent (C6-C60) an aryl or (C4-C60) heteroaryl; R ₁₁₀ , R ₁₁₁ and R ₁₁₂ independently represent hydrogen, deuterium, (C1-C60) alkyl or (C6) -C60) aryl; e is an integer from 1 to 4, f is an integer of 0 or 1; and the alkyl, aryl, heteroaryl, arylamine, alkylamine, ring of Ar ₁₁ and Ar ₁₂ An alkyl or heterocycloalkyl group; the aryl, heteroaryl, aryl or heteroaryl group of Ar ₁₃ ; the aryl or heteroaryl group of Ar ₂₁ and Ar ₂₂ ; or R ₁₁₀ to R ₁₁₂ The alkyl or aryl group may be further substituted with one or more substituents selected from the group consisting of hydrazine, halogen, (C1-C60)alkyl, (C6-C60) aryl, (C4-C60)heteroaryl a 5- or 6-membered heterocycloalkyl group containing one or more heteroatoms selected from N, O and S, (C3-C60)cycloalkyl, tri(C1-C60)alkyldecanealkyl, di(C1) -C60)alkyl (C6-C60) aryldecyl, tris(C6-C60)aryldecyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2- C60) alkynyl, cyano, (C1-C60)alkylamino, (C6-C60) arylamino, (C6-C60) aryl (C1-C60) alkyl, (C6-C60) aryloxy Base, (C1-C60) alkoxy, (C6-C60) arylthio, (C1-C60) alkane Sulfuryl, (C1-C60) alkoxycarbonyl, (C1-C60)alkylcarbonyl, (C6-C60)arylcarbonyl, carboxyl, nitro and hydroxy; formula (6) M ¹ L ¹⁰¹ L ¹⁰² L ¹⁰³ Wherein M ¹ is selected from the group consisting of the following groups: Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 of the Periodic Table of Elements and Group 16; and the ligands L ¹⁰¹ , L ¹⁰² and L ¹⁰³ are independently selected from the following structures: Wherein R ₂₀₁ to R ₂₀₃ independently represent hydrogen, deuterium, (C1-C60)alkyl group having or not containing a halogen substituent, (C6-C60) aryl group having or not containing a (C1-C60) alkyl substituent; Or halogen; R ₂₀₄ to R ₂₁₉ independently represent hydrogen, hydrazine, (C1-C60)alkyl, (C1-C30) alkoxy, (C3-C60)cycloalkyl, (C2-C30)alkenyl, ( C6-C60) aryl, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, SF ₅ , tri(C1-C30)alkyldecyl, di(C1 -C30)alkyl (C6-C30) arylalkyl, tris(C6-C30)aryldecyl, cyano or halogen, and the alkyl, cycloalkyl, alkenyl or aryl of R ₂₀₄ to R ₂₁₉ The group may be further substituted with one or more substituents selected from the group consisting of hydrazine, (C1-C60) alkyl, (C6-C60) aryl and halogen; R ₂₂₀ to R ₂₂₃ independently represent hydrogen, hydrazine, with or without halogen a (C1-C60) alkyl group of a substituent, or a (C6-C60) aryl group having or not containing a (C1-C60) alkyl substituent; R ₂₂₄ and R ₂₂₅ independently represent hydrogen, deuterium, (C1-C60) An alkyl group, a (C6-C60) aryl group or a halogen, or R ₂₂₄ and R ₂₂₅ may be bonded via a (C3-C12)alkylene group or a (C3-C12)alkylene group with or without a fused ring. Alicyclic ring, or a monocyclic or polycyclic aromatic ring rings, and R ₂₂₄ and R ₂₂₅ of the alkyl or aryl, or R ₂₂₄ and R ₂₂₅ via or without a fused ring of (C3-C12) alkylene Or the alicyclic ring formed by the (C3-C12)-alkenyl linkage, or the monocyclic or polycyclic aromatic ring may further be one or more selected from (C1-C60) with or without a halogen substituent Substituent substitution of alkyl, (C1-C30) alkoxy, anthracene, halogen, tri(C1-C30)alkyldecyl, tris(C6-C30)aryldecyl and (C6-C60)aryl; R ₂₂₆ represents (C1-C60)alkyl, (C6-C60)aryl, (C5-C60)heteroaryl or halogen; R ₂₂₇ to R ₂₂₉ independently represent hydrogen, deuterium, (C1-C60)alkyl, ( C6-C60) aryl or halogen, and the alkyl or aryl group of R ₂₂₆ to R ₂₂₉ may be further substituted by halogen or (C1-C60) alkyl substituent; and Q represents , or Wherein R ₃₀₁ to R ₃₁₂ independently represent hydrogen, hydrazine, (C1-C60)alkyl group having or not containing a halogen substituent, (C1-C30) alkoxy group, halogen, (C6-C60) aryl group, cyanide Or a (C5-C60)cycloalkyl group, or R ₃₀₁ to R ₃₁₂ may be bonded to an adjacent substituent via an alkyl or alkenyl group to form a (C5-C7) spiro ring or a (C5-C9) thick group. Ring-bonded, or R ₃₀₁ to R ₃₁₂ may be bonded to R ₂₀₇ or R ₂₀₈ individually via an alkyl or alkenyl group to form a (C5-C7) fused ring. An organic electric field light-emitting device according to claim 2, comprising: a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode; wherein the organic layer comprises one or A plurality of organic electroluminescent compounds of claim 1 and one or more host materials selected from the group consisting of compounds represented by chemical formula (7) or chemical formula (8): chemical formula (7) (Ar ₃₁ ) _g -L ₂₁ - (Ar _{32) h} chemical formula _{(8) (Ar 33) i} -L 22 - (Ar 34) j wherein, L ₂₁ represents (C6-C60) arylene group or a (C4-C60) heteroaryl or an arylene group; L ₂₂ represents stretch anthracene Ar ₃₁ to Ar _{34 are} independently selected from the group consisting of hydrogen, hydrazine, (C1-C60) alkyl, (C1-C30) alkoxy, halogen, (C4-C60)heteroaryl, (C5-C60) cycloalkyl And (C6-C60)aryl; the cycloalkyl, aryl or heteroaryl group of Ar ₃₁ to Ar ₃₄ may be further substituted by one or more substituents selected from the group consisting of one or more (C1-C60)alkyl, (C1-C60)alkoxy, (C3-C60)cycloalkyl, halogen, cyano, tri(C1-C60) alkane, optionally with or without a halogen substituent Base alkyl, di(C1-C60)alkyl (C6-C60) a (C6-C60) aryl group or a (C4-C60) heteroaryl group having a substituent of a group consisting of an aryl decyl group and a tris(C6-C60) aryl decyl group; with or without a halogen substituent (C1) -C60)alkyl, (C1-C60)alkoxy, (C3-C60)cycloalkyl, anthracene, halogen, cyano, tri(C1-C60)alkyldecyl, di(C1-C60)alkyl (C6-C60) arylalkylalkyl and tris(C6-C60)aryldecylalkyl; and g, h, i and j independently represent an integer from 0 to 4. The organic electroluminescent device of claim 2, wherein the organic layer comprises one or more compounds selected from the group consisting of arylamine compounds and styrylarylamine compounds. The organic electroluminescent device of claim 2, wherein the organic layer comprises one or more metals selected from the group consisting of: an organometallic of Group 1 of the Periodic Table of Elements, an organometallic of Group 2, Transition metal, lanthanide metal and d-transition elements of 4 cycles and 5 cycles. An organic electric field light-emitting device according to claim 2, wherein the organic layer comprises an electric field light-emitting layer and a charge generating layer. An organic electric field light-emitting device according to claim 2, wherein a mixed region of a reducing dopant and an organic substance or an oxidizing dopant and an organic layer are disposed on an inner surface of one or both of the electrode pairs. a mixed area of matter. An organic solar cell comprising the organic electroluminescent compound of claim 1 of the invention.