WO2012030145A1 - Novel compounds for organic electronic material and organic electroluminescent device using the same - Google Patents

Novel compounds for organic electronic material and organic electroluminescent device using the same Download PDF

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WO2012030145A1
WO2012030145A1 PCT/KR2011/006412 KR2011006412W WO2012030145A1 WO 2012030145 A1 WO2012030145 A1 WO 2012030145A1 KR 2011006412 W KR2011006412 W KR 2011006412W WO 2012030145 A1 WO2012030145 A1 WO 2012030145A1
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alkyl
organic
compound
heteroaryl
aryl
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PCT/KR2011/006412
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French (fr)
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Soo-Jin Hwang
Hee Choon Ahn
Mi Ae Lee
Seok Keun Yoon
Bong Ok Kim
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority to CN2011800499936A priority Critical patent/CN103201273A/en
Priority to JP2013525846A priority patent/JP5830097B2/en
Publication of WO2012030145A1 publication Critical patent/WO2012030145A1/en

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    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Definitions

  • the present invention relates to novel compounds for organic electronic material and an organic electroluminescent device using the same.
  • electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices.
  • Eastman Kodak first developed an organic EL device using a low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [ Appl. Phys. Lett. 51, 913, 1987].
  • an organic EL device when a charge is applied to an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole are paired and exciton is generated. Light is emitted by using electroluminescence (phosphorescence or fluorescence) in a state that the exciton is inactivated.
  • the organic EL device emits polarization of light at voltage of about 10V and high brightness of about 100 ⁇ 10,000cd/m2.
  • the organic EL device has a feature in that light is emitted in a spectrum ranging from blue color to red color by simply selecting a fluorescent material.
  • the organic EL device is advantageous in that it can be formed on a flexible transparent substrate such as plastic, is operable with relatively low voltage (10 V or lower) as compared to plasma display panels or inorganic EL displays, consumes less power, and provides excellent color.
  • the electroluminescent material In an organic EL device, the most important factor that determines its performance including luminescence efficiency and operation life is the electroluminescent material. Some requirements of the electroluminescent material include high electroluminescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform film and stability.
  • Organic electroluminescent materials are generally classified into high-molecular materials and low-molecular materials.
  • the low-molecular materials include metal complexes and thoroughly organic electroluminescent materials which do not contain metal, from the aspect of molecular structure.
  • Such electroluminescent materials include chelate complexes such as tris(8-quinolinolato)aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bis(styrylarylene) derivatives and oxadiazole derivatives. From those materials, it is reported that light emission of visible region from blue to red can be obtained.
  • electroluminescent materials for red, green and blue
  • OLED organic light-emitting diode
  • the important issue is to develop red, green and blue electroluminescent materials with high efficiency and long life, in order to enhance the overall feature of the organic electroluminescent (EL) devices.
  • the EL materials are classified into host materials and dopant materials. It is generally known that a device structure having the most excellent EL properties can be fabricated with an EL layer prepared by doping a dopant to a host.
  • the desired properties for the host material are high purity and appropriate molecular weight to enable vapor-deposition in vacuo.
  • glass transition temperature and thermal decomposition temperature should be high enough to ensure thermal stability.
  • the host material should have high electrochemical stability for providing long life. It is to be easy to form an amorphous thin film, with high adhesiveness to other adjacent materials but without interlayer migration.
  • the organic EL device When the organic EL device is fabricated by doping technology, a ratio of energy transferred from host molecule to dopant in an excited state does not achieve 100% and a host material as well as dopant emits light. In particular, since the host material emits light in a range of wavelength having larger visibility than the dopant in case of a red light emitting device, color purity is deteriorated due to dull light emission of the host material. If the technology is actually applied, it is required to increase luminescence life and improve durability.
  • CBP is most widely known as a host material for a phosphorescent material.
  • High-efficiency OLEDs using a hole blocking layer comprising BCP, BAlq, etc. are reported.
  • High-performance OLEDs using BAlq derivatives as a host were reported by Pioneer (Japan) and others.
  • an object of the present invention is to provide compounds for organic electronic materials having luminescence efficiency and device operation life improved over existing materials and having superior backbone with appropriate color coordinates in order to solve the aforesaid problems.
  • Another object of the present invention is to provide a highly efficient organic electroluminescent device having long operation life by employing the compounds for organic electronic materials as an electroluminescent material.
  • the compounds for organic electronic materials represented by Chemical Formula 1 below, and an organic electroluminescent device using the same.
  • the compounds for organic electronic materials according to the present invention may be used to manufacture an OLED device having very superior operation life and consuming less power due to improved power efficiency.
  • L 1 and L 2 independently represent a single bond, (C3-C30)cycloalkylene, (C6-C30)arylene or (C3-C30)heteroarylene;
  • X 1 and X 2 independently represent CR 6 or N, except for a case where both X 1 and X 2 are CR 6 ;
  • R 1 through R 6 independently represent hydrogen, deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C3-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)arylthio, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsily
  • the cycloalkylene, arylene and heteroarylene of L 1 and L 2 and the alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl and heteroaryl of R 1 through R 6 may be independently further substituted with one or more selected from the group consisting of deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C3-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)arylthio, mono or di(C1-C30
  • alkyl alkoxy and other substituents containing the “alkyl” moiety include both linear and branched species.
  • the "cycloalkyl” includes polycyclic hydrocarbon ring such as adamantyl with or without substituent(s) or (C7-C30)bicycloalkyl with or without substituent(s) as well as a monocyclic hydrocarbon ring.
  • aryl means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly, 5- or 6-membered, single ring or fused ring, including a plurality of aryls linked by single bond(s).
  • the naphthyl includes 1-naphthyl and 2-naphthyl
  • the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl
  • the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
  • the heteroaryl group includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt.
  • Specific examples thereof include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzois
  • (C1-C30)alkyl includes (C1-C20)alkyl, more specifically (C1-C10)alkyl
  • “(C6-C30)aryl” includes (C6-C20)aryl, more specifically (C6-C12)aryl
  • “(C3-C30)heteroaryl” includes (C3-C20)heteroaryl, more specifically (C3-C12)heteroaryl
  • (C3-C30)cycloalkyl includes (C3-C20)cycloalkyl, more specifically (C3-C7)cycloalkyl
  • “(C2-C30)alkenyl or alkynyl includes (C2-C20)alkenyl or alkylnyl, more specifically (C2-C10)alkenyl or alkylnyl.
  • the compounds for organic electronic materials according to the present invention may be represented by Chemical Formula 2 or 3 below.
  • L 1 and L 2 independently represent a single bond, (C3-C30)cycloalkylene, (C6-C30)arylene or (C3-C30)heteroarylene;
  • R 1 is (C6-C30)aryl or (C3-C30)heteroaryl;
  • R 2 through R 6 are defined as in Chemical Formula 1; the cycloalkylene, arylene and heteroarylene of L 1 and L 2 and the aryl and heteroaryl of R 1 may be independently further substituted with one or more selected from the group consisting of deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C
  • the heteroaryl of R 1 may be selected from the following structures.
  • Y is NR 13 , O or S; Z is NR 13 , CR 14 R 15 , O or S; R 11 through R 15 are independently hydrogen, deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C3-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)arylthio, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C
  • R 1 is selected from the following structures
  • R 2 , R 3 , R 4 , R 5 and R 6 are independently hydrogen
  • L 1 is a single bond or is selected from the following structures:
  • L 2 is a single bond, phenylene or cyclohexylene.
  • the compounds for organic electronic materials according to the present invention may be exemplified by the following compounds, which do not limit the present invention.
  • the compound for an organic electronic material according to the present invention is prepared as shown in Scheme 1 below but is not limited thereto, and may be prepared using a known adjacent of organic synthesis.
  • L 1 , L 2 , X 1 , X 2 and R 1 to R 5 of Chemical Formula 1 are defined as in Chemical Formula 1, and X is a halogen.
  • an organic electroluminescent device which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more compound(s) for organic electronic material represented by Chemical Formula 1.
  • the organic layer comprises an electroluminescent layer, in which the compounds for organic electronic material of Chemical Formula 1 are used as a host material.
  • the phosphorescent dopant used in the organic electroluminescent device of the present invention is not particularly limited, but may be selected from the compounds represented by Chemical Formula 4:
  • M 1 is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16 of the Periodic table, and the ligands L 101 , L 102 and L 103 are independently selected from the following structures:
  • R 201 through R 203 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkyl-substituted or unsubstituted (C6-C30)aryl, or halogen;
  • R 204 through R 219 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted mono- or di(C1-C30)alkylamino, substituted or unsubstituted mono- or di(C6-C30)arylamino, SF5, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, cyano or
  • R 220 through R 223 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl or (C1-C30)alkyl-substituted or unsubstituted (C6-C30)aryl;
  • R 224 and R 225 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or halogen, or R224 and R225 are linked by (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;
  • R 226 represents substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C5-C30)heteroaryl, or halogen;
  • R 227 through R 229 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or halogen;
  • R 231 through R 242 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkoxy, halogen, substituted or unsubstituted (C6-C30)aryl, cyano, or substituted or unsubstituted (C5-C30)cycloalkyl, or each of them may be linked to an adjacent substituent via alkylene or alkenylene to form a spiro ring or a fused ring, or may be linked to R 207 or R 208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
  • the phosphorescent dopant compound of Chemical Formula 4 is exemplified by the following compounds, but is not limited thereto.
  • the organic layer may further include, in addition to the compound for organic electric material represented by Chemical Formula 1, one or more compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds, at the same time.
  • the arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
  • the organic layer may further include, in addition to the compounds for organic electronic materials represented by Chemical Formula 1, one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s).
  • the organic layer may include an electroluminescent layer and a charge generating layer.
  • the organic layer may include, in addition to the compound for organic electric material of Chemical Formula 1, one or more organic electroluminescent layer(s) emitting blue, green or red light at the same time in order to embody a white-emitting organic electroluminescent device.
  • the compounds emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
  • a layer (hereinafter referred to as "surface layer" selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a metal chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. Operation stability may be attained therefrom.
  • the chalcogenide may be, for example, SiO x (1 ⁇ x ⁇ 2), AlO x (1 ⁇ x ⁇ 1.5), SiON, SiAlON, etc.
  • the metal halide may be, for example, LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.
  • the metal oxide may be, for example, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • the organic electroluminescent device it is also preferable to arrange on at least one surface of the pair of electrodes thus manufactured a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant.
  • a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant.
  • the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated.
  • the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent medium are facilitated.
  • Preferable oxidative dopants include various Lewis acids and acceptor compounds.
  • Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. Further, a white-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
  • the compounds for organic electronic material according to the present invention exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life.
  • the present invention is further described with respect to the compounds for organic electronic materials according to the present invention, processes for preparing the same, and luminescence properties of devices employing the same.
  • the following examples are provided for illustrative purposes only and they are not intended to limit the scope of the present invention.
  • An OLED device was manufactured using the compound for organic electronic materials according to the present invention.
  • a transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from a glass for OLED (produced by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
  • an ITO substrate was equipped in a substrate folder of a vacuum deposition apparatus, and 4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum deposition apparatus, which was then evacuated up to 10 -6 torr of vacuum in the chamber.
  • NPB N,N -bis(a-naphthyl)- N,N -diphenyl-4,4'-diamine
  • Compound 3 according to the present invention purified via vacuum sublimation at 10 -6 torr was placed as a host material in one cell of the vacuum deposition apparatus and a bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate ((piq) 2 Ir(acac)) was placed as an electroluminescent dopant in another cell. Then, two materials were evaporated at different rates such that an electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer through doping at 4 to 20 wt%.
  • Alq tris(8-hydroxyquinoline)-aluminum(III)
  • Each compound used in the OLED was purified by vacuum sublimation at 10 -6 torr.
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 4 was used as the host material in the electroluminescent layer.
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 14 was used as the host material in the electroluminescent layer layer.
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 20 was used as the host material in the electroluminescent layer.
  • An OLED device was manufactured by the same method as in Example 1, with the exception that 4,4 -bis(carbazol-9-yl)biphenyl (CBP) was used as the host material in the electroluminescent layer, instead of the compound according to the present invention, and bis(2-methyl-8-quinolinato)(p-phenylphenolato)aluminum(III) (Balq) was used for a hole blocking layer.
  • CBP 4,4 -bis(carbazol-9-yl)biphenyl
  • Balq bis(2-methyl-8-quinolinato)(p-phenylphenolato)aluminum(III)
  • the compounds for organic electronic material according to the present invention have excellent properties compared with the conventional material. Also, an organic electroluminescent device using the compounds for organic electronic material according to the present invention having a fluoranthene substituent as a host material has excellent electroluminescent properties and drops driving voltage by 0.7 ⁇ 1.2 V, thereby increasing power efficiency and improving power consumption.
  • the compounds for organic electronic material according to the present invention exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life.

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Abstract

Provided are novel compounds for organic electronic material and an organic electroluminescent device using the same. Because the compounds for organic electronic material according to the present invention are highly efficient at transporting electrons, crystallization is prevented when manufacturing a device and current properties of the device are improved due to favorably formed layers. Accordingly, OLED devices having improved power efficiency as well as reduced operating voltage can be manufactured.

Description

NOVEL COMPOUNDS FOR ORGANIC ELECTRONIC MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
The present invention relates to novel compounds for organic electronic material and an organic electroluminescent device using the same.
Among display devices, electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices. In 1987, Eastman Kodak first developed an organic EL device using a low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [Appl. Phys. Lett. 51, 913, 1987].
In an organic EL device, when a charge is applied to an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole are paired and exciton is generated. Light is emitted by using electroluminescence (phosphorescence or fluorescence) in a state that the exciton is inactivated. The organic EL device emits polarization of light at voltage of about 10V and high brightness of about 100~10,000cd/㎡. The organic EL device has a feature in that light is emitted in a spectrum ranging from blue color to red color by simply selecting a fluorescent material. The organic EL device is advantageous in that it can be formed on a flexible transparent substrate such as plastic, is operable with relatively low voltage (10 V or lower) as compared to plasma display panels or inorganic EL displays, consumes less power, and provides excellent color.
In an organic EL device, the most important factor that determines its performance including luminescence efficiency and operation life is the electroluminescent material. Some requirements of the electroluminescent material include high electroluminescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform film and stability.
Organic electroluminescent materials are generally classified into high-molecular materials and low-molecular materials. The low-molecular materials include metal complexes and thoroughly organic electroluminescent materials which do not contain metal, from the aspect of molecular structure. Such electroluminescent materials include chelate complexes such as tris(8-quinolinolato)aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bis(styrylarylene) derivatives and oxadiazole derivatives. From those materials, it is reported that light emission of visible region from blue to red can be obtained.
Three electroluminescent materials (for red, green and blue) are employed to realize a full-colored organic light-emitting diode (OLED) display. The important issue is to develop red, green and blue electroluminescent materials with high efficiency and long life, in order to enhance the overall feature of the organic electroluminescent (EL) devices. From the aspect of function, the EL materials are classified into host materials and dopant materials. It is generally known that a device structure having the most excellent EL properties can be fabricated with an EL layer prepared by doping a dopant to a host. Recently, development of organic EL devices with high efficiency and long life comes to the fore as an urgent subject, and particularly urgent is development of a material with far better EL properties as compared to conventional EL materials as considering EL properties required for a medium to large sized OLED panel.
From this point of view, development of a host material is one of the most important issues to be settled. The desired properties for the host material (serving as a solvent and energy conveyer in solid state) are high purity and appropriate molecular weight to enable vapor-deposition in vacuo. In addition, glass transition temperature and thermal decomposition temperature should be high enough to ensure thermal stability. Further, the host material should have high electrochemical stability for providing long life. It is to be easy to form an amorphous thin film, with high adhesiveness to other adjacent materials but without interlayer migration.
When the organic EL device is fabricated by doping technology, a ratio of energy transferred from host molecule to dopant in an excited state does not achieve 100% and a host material as well as dopant emits light. In particular, since the host material emits light in a range of wavelength having larger visibility than the dopant in case of a red light emitting device, color purity is deteriorated due to dull light emission of the host material. If the technology is actually applied, it is required to increase luminescence life and improve durability.
At present, CBP is most widely known as a host material for a phosphorescent material. High-efficiency OLEDs using a hole blocking layer comprising BCP, BAlq, etc. are reported. High-performance OLEDs using BAlq derivatives as a host were reported by Pioneer (Japan) and others.
Figure PCTKR2011006412-appb-I000001
Although these materials provide good electroluminescence characteristics, they are disadvantageous in that degradation may occur during the high-temperature deposition process in vacuum because of low glass transition temperature and poor thermal stability. Since the power efficiency of an OLED is given by (π / voltage) × current efficiency, the power efficiency is inversely proportional to the voltage. High power efficiency is required to reduce the power consumption of an OLED. Actually, OLEDs using phosphorescent materials provide much better current efficiency (cd/A) than those using fluorescent materials. However, when the existing materials such as BAlq, CBP, etc. are used as a host of the phosphorescent material, there is no significant advantage in power efficiency (lm/W) over the OLEDs using fluorescent materials because of high driving voltage. Further, the OLED devices do not have satisfactory operation life. Therefore, development of more stable, higher-performance host materials is required.
Accordingly, an object of the present invention is to provide compounds for organic electronic materials having luminescence efficiency and device operation life improved over existing materials and having superior backbone with appropriate color coordinates in order to solve the aforesaid problems. Another object of the present invention is to provide a highly efficient organic electroluminescent device having long operation life by employing the compounds for organic electronic materials as an electroluminescent material.
Provided are compounds for organic electronic materials represented by Chemical Formula 1 below, and an organic electroluminescent device using the same. With superior luminescence efficiency and excellent life property, the compounds for organic electronic materials according to the present invention may be used to manufacture an OLED device having very superior operation life and consuming less power due to improved power efficiency.
[Chemical Formula 1]
Figure PCTKR2011006412-appb-I000002
wherein,
L1 and L2 independently represent a single bond, (C3-C30)cycloalkylene, (C6-C30)arylene or (C3-C30)heteroarylene;
X1 and X2 independently represent CR6 or N, except for a case where both X1 and X2 are CR6;
R1 through R6 independently represent hydrogen, deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C3-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)arylthio, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, nitro or hydroxyl; and
the cycloalkylene, arylene and heteroarylene of L1 and L2 and the alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl and heteroaryl of R1 through R6 may be independently further substituted with one or more selected from the group consisting of deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C3-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)arylthio, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, nitro and hydroxyl;
the heteroarylene, heterocycloalkyl and heteroaryl include one or more heteroatom(s) selected from the group consisting of B, N, O, S, P(=O), Si and P;
except for a case where
Figure PCTKR2011006412-appb-I000003
is hydrogen.
In the present invention, "alkyl", "alkoxy" and other substituents containing the "alkyl" moiety include both linear and branched species. In the present invention, the "cycloalkyl" includes polycyclic hydrocarbon ring such as adamantyl with or without substituent(s) or (C7-C30)bicycloalkyl with or without substituent(s) as well as a monocyclic hydrocarbon ring. In the present invention, "aryl" means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly, 5- or 6-membered, single ring or fused ring, including a plurality of aryls linked by single bond(s). Specific examples thereof include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto. The naphthyl includes 1-naphthyl and 2-naphthyl, the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl. In the present invention, "heteroaryl" means an aryl group containing 1 to 4 heteroatom(s) selected from the group consisting of B, N, O, S, P(=O), Si and P as aromatic ring backbone atom(s), the remaining aromatic ring backbone atom being carbon, and is exemplified by 5- or 6-membered monocyclic heteroaryl and polycyclic heteroaryl condensed with one or more benzene rings, which may be partially saturated. Further, the heteroaryl includes more than one heteroaryls linked by single bond(s). The heteroaryl group includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt. Specific examples thereof include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, benzodioxolyl, etc., an N-oxide thereof (e.g., pyridyl N-oxide, quinolyl N-oxide, etc.), a quaternary salt thereof, etc., but are not limited thereto.
In the present invention, "(C1-C30)alkyl" includes (C1-C20)alkyl, more specifically (C1-C10)alkyl, and "(C6-C30)aryl" includes (C6-C20)aryl, more specifically (C6-C12)aryl. Also, "(C3-C30)heteroaryl" includes (C3-C20)heteroaryl, more specifically (C3-C12)heteroaryl, and "(C3-C30)cycloalkyl" includes (C3-C20)cycloalkyl, more specifically (C3-C7)cycloalkyl. Also, "(C2-C30)alkenyl or alkynyl" includes (C2-C20)alkenyl or alkylnyl, more specifically (C2-C10)alkenyl or alkylnyl.
Furthermore, the compounds for organic electronic materials according to the present invention may be represented by Chemical Formula 2 or 3 below.
[Chemical Formula 2]
Figure PCTKR2011006412-appb-I000004
[Chemical Formula 3]
Figure PCTKR2011006412-appb-I000005
wherein
L1 and L2 independently represent a single bond, (C3-C30)cycloalkylene, (C6-C30)arylene or (C3-C30)heteroarylene; R1 is (C6-C30)aryl or (C3-C30)heteroaryl; R2 through R6 are defined as in Chemical Formula 1; the cycloalkylene, arylene and heteroarylene of L1 and L2 and the aryl and heteroaryl of R1 may be independently further substituted with one or more selected from the group consisting of deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C3-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)arylthio, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, nitro and hydroxyl.
The heteroaryl of R1 may be selected from the following structures.
Figure PCTKR2011006412-appb-I000006
wherein
Y is NR13, O or S; Z is NR13, CR14R15, O or S; R11 through R15 are independently hydrogen, deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C3-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)arylthio, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, nitro or hydroxyl; A is a monocyclic or polycyclic aromatic ring or a monocyclic or polycyclic heteroaromatic ring.
Specifically, R1 is selected from the following structures;
Figure PCTKR2011006412-appb-I000007
Figure PCTKR2011006412-appb-I000008
Figure PCTKR2011006412-appb-I000009
Figure PCTKR2011006412-appb-I000010
R2, R3, R4, R5 and R6 are independently hydrogen;
L1 is a single bond or is selected from the following structures:
Figure PCTKR2011006412-appb-I000011
; and
L2 is a single bond, phenylene or cyclohexylene.
More specifically, the compounds for organic electronic materials according to the present invention may be exemplified by the following compounds, which do not limit the present invention.
Figure PCTKR2011006412-appb-I000012
Figure PCTKR2011006412-appb-I000013
Figure PCTKR2011006412-appb-I000014
Figure PCTKR2011006412-appb-I000015
Figure PCTKR2011006412-appb-I000016
Figure PCTKR2011006412-appb-I000017
Figure PCTKR2011006412-appb-I000018
The compound for an organic electronic material according to the present invention is prepared as shown in Scheme 1 below but is not limited thereto, and may be prepared using a known adjacent of organic synthesis.
[Scheme 1]
Figure PCTKR2011006412-appb-I000019
wherein
L1, L2, X1, X2 and R1 to R5 of Chemical Formula 1 are defined as in Chemical Formula 1, and X is a halogen.
Provided is an organic electroluminescent device, which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more compound(s) for organic electronic material represented by Chemical Formula 1. The organic layer comprises an electroluminescent layer, in which the compounds for organic electronic material of Chemical Formula 1 are used as a host material.
When the compounds for organic electronic material of Chemical Formula 1 are used as a host in the electroluminescent layer, one or more phosphorescent dopant(s) is included. The phosphorescent dopant used in the organic electroluminescent device of the present invention is not particularly limited, but may be selected from the compounds represented by Chemical Formula 4:
[Chemical Formula 4]
M1L101L102L103
wherein
M1 is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16 of the Periodic table, and the ligands L101, L102 and L103 are independently selected from the following structures:
Figure PCTKR2011006412-appb-I000020
Figure PCTKR2011006412-appb-I000021
Figure PCTKR2011006412-appb-I000022
Figure PCTKR2011006412-appb-I000023
wherein R201 through R203 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkyl-substituted or unsubstituted (C6-C30)aryl, or halogen;
R204 through R219 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted mono- or di(C1-C30)alkylamino, substituted or unsubstituted mono- or di(C6-C30)arylamino, SF5, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, cyano or halogen;
R220 through R223 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl or (C1-C30)alkyl-substituted or unsubstituted (C6-C30)aryl;
R224 and R225 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or halogen, or R224 and R225 are linked by (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;
R226 represents substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C5-C30)heteroaryl, or halogen;
R227 through R229 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or halogen; and
Q is
Figure PCTKR2011006412-appb-I000024
,
Figure PCTKR2011006412-appb-I000025
or
Figure PCTKR2011006412-appb-I000026
, wherein R231 through R242 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkoxy, halogen, substituted or unsubstituted (C6-C30)aryl, cyano, or substituted or unsubstituted (C5-C30)cycloalkyl, or each of them may be linked to an adjacent substituent via alkylene or alkenylene to form a spiro ring or a fused ring, or may be linked to R207 or R208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
The phosphorescent dopant compound of Chemical Formula 4 is exemplified by the following compounds, but is not limited thereto.
Figure PCTKR2011006412-appb-I000027
Figure PCTKR2011006412-appb-I000028
Figure PCTKR2011006412-appb-I000029
Figure PCTKR2011006412-appb-I000030
Figure PCTKR2011006412-appb-I000031
Figure PCTKR2011006412-appb-I000032
Figure PCTKR2011006412-appb-I000033
Figure PCTKR2011006412-appb-I000034
In the organic electronic device of the present invention, the organic layer may further include, in addition to the compound for organic electric material represented by Chemical Formula 1, one or more compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds, at the same time. The arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
Further, in the organic electroluminescent device of the present invention, the organic layer may further include, in addition to the compounds for organic electronic materials represented by Chemical Formula 1, one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s). The organic layer may include an electroluminescent layer and a charge generating layer.
Further, the organic layer may include, in addition to the compound for organic electric material of Chemical Formula 1, one or more organic electroluminescent layer(s) emitting blue, green or red light at the same time in order to embody a white-emitting organic electroluminescent device. The compounds emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
In the organic electroluminescent device of the present invention, a layer (hereinafter referred to as "surface layer" selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a metal chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. Operation stability may be attained therefrom. The chalcogenide may be, for example, SiOx (1 ≤ x ≤ 2), AlOx (1 ≤ x ≤ 1.5), SiON, SiAlON, etc. The metal halide may be, for example, LiF, MgF2, CaF2, a rare earth metal fluoride, etc. The metal oxide may be, for example, Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
In the organic electroluminescent device according to the present invention, it is also preferable to arrange on at least one surface of the pair of electrodes thus manufactured a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant. In that case, since the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated. In addition, since the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent medium are facilitated. Preferable oxidative dopants include various Lewis acids and acceptor compounds. Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. Further, a white-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
Since the compounds for organic electronic material according to the present invention exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life.
The present invention is further described with respect to the compounds for organic electronic materials according to the present invention, processes for preparing the same, and luminescence properties of devices employing the same. However, the following examples are provided for illustrative purposes only and they are not intended to limit the scope of the present invention.
[Preparative Example 1] Preparation of Compound 4
Figure PCTKR2011006412-appb-I000035
Preparation of Compound 1-1
10 g (49.5 mmol) of 1-bromo-2-nitrobenzene, 10.2 g (59.3 mmol) of 1-naphthalene boronic acid, 200 mL of toluene, 50 mL of ethanol and 50 mL of water were mixed and then added with 2.9 g (2.5 mmol) of Pd(PPh3)4 and 20.5 g (148.3 mmol) of potassium carbonate. This mixture was stirred at 120℃ for 5 hours and then cooled to room temperature, after which the reaction was terminated with 40 mL of aqueous ammonium chloride. The mixture thus obtained was extracted with 500 mL of EA and then washed with 100 mL of distilled water. The resultant organic layer was dried with anhydrous MgSO4, treated under reduced pressure to remove the organic solvent, and then purified using silica gel column chromatography, thus obtaining Compound 1-1 (10 g, 81%).
Preparation of Compound 1-2
10 g (40.1 mmol) of Compound 1-1 was dissolved in 100 mL of 1,2-dichlorobenzene, and 100 mL of triethoxyphosphine was then added thereto. This reaction mixture was stirred at 150℃ for 20 hours and then cooled to room temperature, and the solvents, namely, 1,2-dichlorobenzene and triethoxyphosphine were removed using vacuum distillation. The remaining organic material was extracted with 300 mL of EA, and then washed with 40 mL of distilled water. The resultant organic layer was dried with anhydrous MgSO4, treated under reduced pressure to remove the organic solvent, and then purified using silica gel column chromatography, thus obtaining Compound 1-2 (7 g, 80%).
Preparation of Compound 1-3
20 g (92 mmol) of Compound 1-2 and 43.5 g (184 mmol) of 1-bromo-4-iodobenzene were dissolved in 500 mL of toluene, added with 8.8 g (46 mmol) of CuI, 6.2 mL (92 mmol) of diaminoethane and 58.7 g (276 mmol) of K3PO4, and then refluxed for 30 hours. This reaction mixture was cooled to room temperature, after which the reaction was terminated with 50 mL of 2.0M aqueous hydrochloric acid, and the mixture thus obtained was extracted with 1 L of EA and then washed with 200 mL of distilled water. The resultant organic layer was dried with anhydrous MgSO4, treated under reduced pressure to remove the organic solvent, and then purified using silica gel column chromatography, thus obtaining Compound 1-3 (19 g, 56%).
Preparation of Compound 1-4
19 g (51 mmol) of Compound 1-3 was dissolved in 250 mL of THF and then cooled to -78℃, after which 24.5 mL of n-BuLi (2.5 M in hexane) was added thereto at -78℃. This mixture was stirred at -78℃ for 1 hour, added with 8.5 mL of B(OMe)3, and stirred for 2 hours, and the reaction was terminated with 100 mL of aqueous ammonium chloride. Subsequently, the mixture thus obtained was extracted with 500 mL of EA, and then washed with 100 mL of distilled water. The resultant organic layer was dried with anhydrous MgSO4, treated under reduced pressure to remove the organic solvent, and recrystallized, thus obtaining Compound 1-4 (14 g, 81%).
Preparation of Compound 2-1
50 g (247 mmol) of fluoranthene was dissolved in 1 L of nitrobenzene, and 12 mL (234.7 mmol) of bromine diluted with 200 mL of nitrobenzene was slowly added in droplets thereto. After the solution was completely added in droplets, the reaction solution was stirred at room temperature for 20 hours. The reaction solution was added with 500 mL of aqueous saturated sodium thiosulfate chloride so that the reaction was terminated. The mixture thus obtained was extracted with 3 L of EA and then washed with 1 L of distilled water. The resultant organic layer was dried with anhydrous MgSO4, treated under reduced pressure to remove the organic solvent, filtered using silica gel, and then recrystallized, thus obtaining Compound 2-1 (65 g, 94%).
Preparation of Compound 2-2
24.5 g (87.1 mmol) of Compound 2-1 was dissolved in 500 mL of THF, cooled to -78℃, added with 45 mL of n-BuLi (2.5 M in hexane), and then stirred for 1 hour. Subsequently, this mixture was added with 15 mL of B(OMe)3 and stirred for 2 hours, and the reaction was terminated with 250 mL of aqueous ammonium chloride. The mixture thus obtained was extracted with 1 L of EA and then washed with 200 mL of distilled water. The resultant organic layer was dried with anhydrous MgSO4, treated under reduced pressure to remove the organic solvent, and then recrystallized, thus obtaining Compound 2-2 (14 g, 65%).
Preparation of Compound 2-3
8.1 g (40.6 mmol) of 2,4-dichloroquinazoline, 10 g (40.6 mmol) of Compound 2-2, 200 mL of toluene, 50 mL of ethanol, and 50 mL of water were mixed and then added with 1.9 g (1.64 mmol) of Pd(PPh3)4 and 12.9 g (122 mmol) of K2CO3. This mixture was stirred at 120℃ for 5 hours, and cooled to room temperature, after which the reaction was terminated with 200 mL of aqueous ammonium chloride. The mixture thus obtained was extracted with 500 mL of EA and then washed with 50 mL of distilled water. The resultant organic layer was dried with anhydrous MgSO4, treated under reduced pressure to remove the organic solvent, filtered using silica gel, and then recrystallized, thus obtaining Compound 2-3 (10 g, 68%).
Preparation of Compound 4
5.0 g (13.7 mmol) of Compound 2-3 and 5.54 g (16.4 mmol) of Compound 1-4 were mixed with 100 mL of toluene, 20 mL of ethanol and 20 mL of water, after which 1.6 g (1.4mmol) of Pd(PPh3)4 and 5.7 g (41.1mmol) of K2CO3 were added thereto. This mixture was stirred at 120℃ for 5 hours and cooled to room temperature, and the reaction was terminated with 20 mL of aqueous ammonium chloride. The mixture thus obtained was extracted with 250 mL of EA and then washed with 30 mL of distilled water. The resultant organic layer was dried with anhydrous MgSO4, treated under reduced pressure to remove the organic solvent, filtered using silica gel, and then recrystallized, thus obtaining Compound 4 (5.9 g, 69%).
MS/FAB: 621.22(found), 621.73(calculated)
[Example 1] Manufacture of OLED device using the compound for organic electronic material according to the present invention
An OLED device was manufactured using the compound for organic electronic materials according to the present invention. First, a transparent electrode ITO thin film (15 Ω/□) obtained from a glass for OLED (produced by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use. Then, an ITO substrate was equipped in a substrate folder of a vacuum deposition apparatus, and 4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum deposition apparatus, which was then evacuated up to 10-6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate 2-TNATA, thereby depositing a hole injection layer having a thickness of 60 nm on the ITO substrate. Subsequently, N,N-bis(a-naphthyl)-N,N-diphenyl-4,4'-diamine (NPB) was placed in another cell of the vacuum deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby depositing a hole transport layer having a thickness of 20 nm on the hole injection layer. Further, Compound 3 according to the present invention purified via vacuum sublimation at 10-6 torr was placed as a host material in one cell of the vacuum deposition apparatus and a bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate ((piq)2Ir(acac)) was placed as an electroluminescent dopant in another cell. Then, two materials were evaporated at different rates such that an electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer through doping at 4 to 20 wt%. Subsequently, tris(8-hydroxyquinoline)-aluminum(III) (Alq) was deposited with a thickness of 20 nm as an electron transport layer on the electroluminescent layer. Then, after depositing lithium quinolate (Liq) with a thickness of 1 to 2 nm as an electron injection layer, an Al cathode having a thickness of 150 nm was formed using another vacuum vapor deposition apparatus to manufacture an OLED.
Each compound used in the OLED was purified by vacuum sublimation at 10-6torr.
As a result, a current of 14.0 mA/㎠ flowed at a voltage of 6.5 V, and a red light of 1052 cd/㎠ was emitted.
[Example 2]
An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 4 was used as the host material in the electroluminescent layer.
As a result, a current of 14.0 mA/㎠ flowed at a voltage of 7.5 V, and a red light of 1060 cd/㎠ was emitted.
[Example 3]
An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 14 was used as the host material in the electroluminescent layer layer.
As a result, a current of 14.1 mA/㎠ flowed at a voltage of 6.8 V, and a red light of 1030 cd/㎠ was emitted.
[Example 4]
An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 20 was used as the host material in the electroluminescent layer.
As a result, a current of 14.2 mA/㎠ flowed at a voltage of 6.4 V, and a red light of 1048 cd/㎠ was emitted.
[Comparative Example 1]
An OLED device was manufactured by the same method as in Example 1, with the exception that 4,4 -bis(carbazol-9-yl)biphenyl (CBP) was used as the host material in the electroluminescent layer, instead of the compound according to the present invention, and bis(2-methyl-8-quinolinato)(p-phenylphenolato)aluminum(III) (Balq) was used for a hole blocking layer.
As a result, a current of 15.3 mA/㎠ flowed at a voltage of 7.5 V, and a red light of 1000 cd/㎠ was emitted.
The compounds for organic electronic material according to the present invention have excellent properties compared with the conventional material. Also, an organic electroluminescent device using the compounds for organic electronic material according to the present invention having a fluoranthene substituent as a host material has excellent electroluminescent properties and drops driving voltage by 0.7 ~ 1.2 V, thereby increasing power efficiency and improving power consumption.
Although the preferred embodiments of the present invention have been disclosed for illustrative purposes, those skilled in the art will appreciate that various modifications, additions, and substitutions are possible, without departing from the scope and spirit of the invention as disclosed in the accompanying claims.
Since the compounds for organic electronic material according to the present invention exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life.

Claims (10)

  1. A compound for organic electronic material represented by Chemical Formula 1 below:
    [Chemical Formula 1]
    Figure PCTKR2011006412-appb-I000036
    wherein,
    L1 and L2 independently represent a single bond, (C3-C30)cycloalkylene, (C6-C30)arylene or (C3-C30)heteroarylene;
    X1 and X2 independently represent CR6 or N, except for a case where both X1 and X2 are CR6;
    R1 through R6 independently represent hydrogen, deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C3-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)arylthio, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, nitro or hydroxyl; and
    the cycloalkylene, arylene and heteroarylene of L1 and L2 and the alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl and heteroaryl of R1 through R6 may be independently further substituted with one or more selected from the group consisting of deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C3-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)arylthio, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, nitro and hydroxyl;
    the heteroarylene, heterocycloalkyl and heteroaryl include one or more heteroatom(s) selected from the group consisting of B, N, O, S, P(=O), Si and P;
    except for a case where
    Figure PCTKR2011006412-appb-I000037
    is hydrogen.
  2. The compound for organic electronic material according to claim 1, which is represented by Chemical Formula 2 or 3 below:
    [Chemical Formula 2]
    Figure PCTKR2011006412-appb-I000038
    [Chemical Formula 3]
    Figure PCTKR2011006412-appb-I000039
    wherein
    L1 and L2 independently represent a single bond, (C3-C30)cycloalkylene, (C6-C30)arylene or (C3-C30)heteroarylene; R1 is (C6-C30)aryl or (C3-C30)heteroaryl; R2 through R6 are defined as in claim 1; the cycloalkylene, arylene and heteroarylene of L1 and L2 and the aryl and heteroaryl of R1 may be independently further substituted with one or more selected from the group consisting of deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C3-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)arylthio, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, nitro and hydroxyl.
  3. The compound for organic electronic material according to claim 1, wherein the R1 is a heteroaryl selected from following structures.
    Figure PCTKR2011006412-appb-I000040
    wherein
    Y is NR13, O or S; Z is NR13, CR14R15, O or S; R11 through R15 are independently hydrogen, deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C3-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)arylthio, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, nitro or hydroxyl; A is a monocyclic or polycyclic aromatic ring or a monocyclic or polycyclic heteroaromatic ring.
  4. The compound for organic electronic material according to claim 1, wherein the R1 is selected from following structures:
    Figure PCTKR2011006412-appb-I000041
    Figure PCTKR2011006412-appb-I000042
    Figure PCTKR2011006412-appb-I000043
    Figure PCTKR2011006412-appb-I000044
    R2, R3, R4, R5 and R6 are independently hydrogen;
    L1 is a single bond or is selected from the following structures:
    Figure PCTKR2011006412-appb-I000045
    ; and
    L2 is a single bond, phenylene or cyclohexylene.
  5. The compound for organic electronic material according to claim 1, which is selected from following compounds:
    Figure PCTKR2011006412-appb-I000046
    Figure PCTKR2011006412-appb-I000047
    Figure PCTKR2011006412-appb-I000048
    Figure PCTKR2011006412-appb-I000049
    Figure PCTKR2011006412-appb-I000050
    Figure PCTKR2011006412-appb-I000051
    Figure PCTKR2011006412-appb-I000052
  6. An organic electroluminescent device comprising the compound for organic electronic material according to any one of claims 1 to 5.
  7. The organic electroluminescent device according to claim 6, which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more compound(s) for organic electronic material and one or more phosphorescent dopant(s).
  8. The organic electroluminescent device according to claim 7, wherein the organic layer further comprises one or more amine compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds, or one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements of the Periodic Table or complex compound(s).
  9. The organic electroluminescent device according to claim 7, wherein the organic layer comprises an electroluminescent layer and a charge generating layer.
  10. The organic electroluminescent device according to claim 7, wherein the organic layer further comprises one or more organic electroluminescent layers emitting red, green or blue light to emit white light.
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