WO2019078620A1

WO2019078620A1 - Novel compound and organic light-emitting device using same

Info

Publication number: WO2019078620A1
Application number: PCT/KR2018/012273
Authority: WO
Inventors: 윤준; 윤주용; 김연환; 홍완표
Original assignee: 주식회사 엘지화학
Priority date: 2017-10-20
Filing date: 2018-10-17
Publication date: 2019-04-25

Abstract

Provided are a novel compound and an organic light-emitting device using the same.

Description

Title of the Invention

Novel compounds and organic light emitting devices using the same

TECHNICAL FIELD

Cross-reference with related application (s)

This application claims the benefit of priority based on Korean Patent Application No. 10-2017-0136519, dated October 20, 2017, and Korean Patent Application No. 10-2018-0123424, dated October 16, 2018, The entire contents of which are incorporated herein by reference. The present invention relates to a novel compound and an organic light emitting device comprising the same.

BACKGROUND ART [0002]

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. The organic light emitting device using the organic light emitting phenomenon has been conducted a wide viewing angle, excellent contrast, it has a quick ungdap time, luminance, driving ^"voltage and ungdap rate characteristics are excellent by many studies. The organic light emitting device generally has a structure including an anode and a cathode, and an organic layer between the anode and the cathode. The organic material layer may have a multilayer structure composed of different materials in order to improve the efficiency and stability of the organic light emitting device. For example, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of the organic light emitting diode, holes are injected in the anode, electrons are injected into the organic layer in the cathode, and excitons are formed when injected holes and electrons meet. The light is emitted when the axon falls back to the floor. There is a continuing need for the development of new materials for the organic materials used in such organic light emitting devices.

[Prior Art Document] [Patent Literature]

(Patent Document 0001) Korean Patent Publication No. 10-2000-0051826

DISCLOSURE OF THE INVENTION

[Problem to be solved]

The present invention relates to a novel compound and an organic light emitting device comprising the same.

MEANS FOR SOLVING THE PROBLEMS

The present invention provides a compound represented by the following formula (1): < EMI ID =

In Formula 1,

Ri and R ₂ are each independently selected from the group consisting of hydrogen, substituted or unsubstituted d-so alkyl, substituted or unsubstituted d-60 alkoxy, substituted or unsubstituted C halo haloalkyl, substituted or unsubstituted haloalkoxy, (C o alkyl) silyl, substituted or unsubstituted C ₆ _ ₆₀ aryl, or substituted or unsubstituted C ₂ - ₆₀ heteroaryl containing 0 or more of N, Si and S ,

R ₃ and R ₄ are each independently hydrogen, deuterium, substituted or unsubstituted d-60 alkyl, substituted or unsubstituted CMO alkoxy, substituted or unsubstituted ( ₆₀ haloalkyl, substituted or unsubstituted haloalkoxy, (D-60 alkyl) silyl, or a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl containing at least one of O, N, Si and S,

Ar is C ₆ - and ₆₀ by interrogating aryl, wherein said C ₆ - - ₆₀ aryl, or 0, N, C _2, including one or more of Si and S ₆₀ aryl, or C ₂ - ₆₀ heteroaryl, substituted Unsubstituted d- ₆₀ alkyl, substituted or unsubstituted d-60 alkoxy, substituted or unsubstituted d-so haloalkyl, substituted or unsubstituted d- ₆₀ haloalkoxy, halogen, cyano, Lt; / RTI >< RTI ID = 0.0 > Lt; / RTI > to 5 substituents. The present invention also relates to a plasma display panel comprising a first electrode; A second electrode facing the first electrode; And at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound represented by Formula 1 do.

【Effects of the Invention】

The compound represented by the general formula (1) can be used as a material of an organic material layer of an organic light emitting device and can improve the efficiency, the driving voltage and / or the lifetime of the organic light emitting device. In particular, the compound represented by Formula 1 can be used as a hole injecting, hole transporting, hole injecting and transporting, light emitting, electron transporting, or electron injecting material.

BRIEF DESCRIPTION OF THE DRAWINGS

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig.

2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.

3 is a cross-sectional view of a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, an electron blocking layer 9, a light emitting layer 7, an electron transporting layer 8, And a cathode (4).

4 is a sectional view showing the structure of the substrate 1, the anode 2, the hole injecting layer 5, the first positive hole injecting layer 11, the electron blocking layer 9, the first light emitting layer 9, the first electron transporting layer 12, The electron transport layer 18, the electron injection layer 8, and the cathode (not shown) are formed on the surface of the first electrode layer 14, the P-type charge generation layer 15, the second hole transport layer 16, the second light emitting layer 17, 4). &Lt; / RTI >

DETAILED DESCRIPTION OF THE INVENTION

Hereinafter, the present invention will be described in detail in order to facilitate understanding of the present invention. The present invention provides a compound represented by the above formula (1). In the present specification,

Or a linkage to another substituent. . As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; Cycloalkyl groups; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; Or a heterocyclic group containing at least one of N, O and S atoms, or a substituted or unsubstituted one in which at least two of the above-exemplified substituents are linked to each other . For example, the "substituent group to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected. In the present specification, the carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it can be a compound of the following structural formula

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto. In the present specification, the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group. In the present specification, examples of the halogen group include fluorine, chlorine, bromine and iodine. In the present specification, the alkyl group may be linear or branched, The number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment of the present invention, the number of carbon atoms of the alkyl group is 1 to 10. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert- Pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, heptyl, heptyl, heptyl, heptyl, methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylnaphthyl, 1-methylhexyl, cyclopentylmethyl, cycloheptylmethyl, cyclohexylmethyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylnucyl, 5-methylnucyl and the like. In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl and styrenyl groups. In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3- Dimethylcyclopentyl, dimethylcyclopentyl, dimethylcyclohexyl, dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2-methylcyclohexyl, But are not limited thereto. In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group. In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. In the case of the fluorenyl group,

And the like. However, the present invention is not limited thereto. In the present specification, the heterocyclic group is a heterocyclic group containing at least one of 0, N, Si and S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole thiazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, an isoquinoline group, an indole group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, Carbazole group, benzoxazole group, Benzothiazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthrol ine, isoxazolyl group, thiadiazolyl group, phenothiazyl group, phenothiazyl group, And dibenzofuranyl groups, but are not limited thereto. In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the alkyl group described above. In the present specification, the heteroaryl among the heteroarylamines can be applied to the description of the above-mentioned heterocyclic groups. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group. In the present specification, the description of the aryl group described above can be applied except that arylene is a divalent group. In the present specification, the description of the above-mentioned Heteroglyphic group can be applied, except that the heteroarylene is divalent. In the present specification, the description of the above-mentioned aryl group or cycloalkyl group can be applied except that the hydrocarbon ring is not a monovalent group and two substituents are bonded to each other. In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heterocyclic ring is not a monovalent group and two substituents are bonded to each other. In the above formula (1), preferably, and each of R 3 and R 4 are each independently a cyano or a 2, 3, 5, 6-tetrafluoro-4-cyanophenyl. Preferably, each of ¾ and R4 is independently hydrogen or deuterium. Preferably, the compound represented by the above formula (1) is represented by the following general formula 1-1, 1-2, 1-3, or 1-4 ^'

[Formula 1-1]

In Formulas 1-1, 1-2, 1-3 and 1-4,

i and R ₂ are as defined above. Preferably, Ar is phenyl, wherein said phenyl is substituted or unsubstituted d-60 alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted each of which is substituted with one to five substituents each independently selected from the group consisting of halogen, d-60 haloalkyl, substituted or unsubstituted d- ₆₀ haloalkoxy, halogen, cyano, and tri (d, Preferably, Ar is phenyl, wherein said phenyl is substituted with one to five substituents each selected from the group consisting of fluoro, trifluoromethyl, trifluoromethyl, and cyano. Preferably, Ar is any one selected from the group consisting of:















The present invention also provides a compound represented by Chemical Formula 1, for example, and a process for preparing the same.

In the above reaction formula 1, the definitions other than X are as defined above, and X is halogen and preferably bromo or chloro. The step 1 is preferably carried out in the presence of a palladium catalyst and a base as a Suzuki coupling reaction, and the reaction for the Suzuki coupling reaction can be changed as known in the art. Step 2 is preferably carried out in the presence of a base as a quinone phenazine condensation reaction. The step 3 is preferably carried out as a dehydrogenation reaction in the presence of N-bromosuccinimide. The above production method can be more specific in the production example to be described later. Also, the present invention provides an organic light emitting device including the compound represented by Formula 1. For example, the present invention provides a method of manufacturing a semiconductor device, A second electrode provided opposite to the first electrode; And one or more organic layers disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound represented by Formula 1 do. The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as organic layers. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers. The organic material layer may include a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes, and the hole injecting layer, the hole transporting layer, And a compound to be displayed. For example, the organic material layer includes a hole injection layer, and the hole injection layer is made of the compound alone or doped with the compound. In addition, the organic layer includes a doped hole transport layer, and the doped hole injection layer is formed by doping the hole transport material with the compound. In addition, the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by the general formula (1). In particular, the compound according to the present invention can be used as a diskette of a light emitting layer. The organic material layer may include an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound represented by the above formula (1). Further, the electron transporting layer, the electron injecting layer, or the layer which simultaneously transports electrons and injects electrons includes the compound represented by the above formula (1). The organic material layer may include a light emitting layer and an electron transporting layer, and the electron transporting layer may include a compound represented by the general formula (1). In addition, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting diode according to an embodiment of the present invention is illustrated in FIGS. Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer. 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is. In such a structure, the compound represented by Formula 1 may be one of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer Or more. 3 is a cross-sectional view of a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, an electron blocking layer 9, a light emitting layer 7, an electron transporting layer 8, And a cathode (4). In such a structure, the compound represented by Formula 1 may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting layer. A first stack for emitting light of a first color, a second stack for emitting light of a second color, and a second stack for emitting light of a second color are provided between the first electrode and the second electrode, Wherein the charge generation layer comprises an N-type charge generation layer located adjacent to the first stack and a P-type charge generation layer adjacent to the system stack, The organic material layer constitutes the P-type charge generation layer, and the P-type charge generation layer may be composed of the compound alone or may be doped with the compound. A first stack for emitting light of a first color and a second stack for emitting light of a second color are disposed between the first electrode and the second electrode, Wherein the charge generation layer comprises an N-type charge generation layer located adjacent to the first stack and a P-type charge generation layer located adjacent to the second stack, The organic material layer may constitute the P-type charge generation layer, and the P-type charge generation layer may be formed by doping the hole transporting material with the compound. The above example is shown in Fig. Fig. 4 is a schematic diagram showing the structure of the substrate 1, the anode 2, the hole injection layer 5, the gate 1 hole transport layer 11, the electron blocking layer 9, the system 1 light emitting layer 9, The N-type charge generation layer 14, the P-type charge generation layer 15, the second dual hole transport layer 16, the second light emitting layer 17, the second electron transport layer 18, the electron injection layer 8, 4) are shown. The organic light emitting device may further include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer. The organic light emitting device according to the present invention, at least one layer of said organic material layer ^above, may be manufactured in materials and methods known in the art, except that it comprises a compound represented by the general formula (1). In addition, when the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials. For example, the organic light emitting device according to the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a metal oxide or a metal oxide having conductivity, or a metal oxide having conductivity on the substrate, may be formed on the substrate by using a PVD (physico-chemical vapor deposition) method such as sputtering or e-beam evaporation To form an anode, an organic layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed on the anode, and then a substance usable as a cathode can be deposited thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate. In addition, the compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto. In addition to such a method, an organic light emitting device can be manufactured by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto. In one example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode and the second electrode is a cathode. As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted to the organic material layer. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ΖηΟ: Α1 SN0 or _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene KPEDOT), polypyrrole and polyaniline. The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lyrium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but the present invention is not limited thereto. The hole injecting layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. The HOMO highest occupied mole ar orbital of the hole injecting material is determined by the work function of the anode material,

H0M0. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, nuclear nitrile-tetracyclopentene-based organic materials, Quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and polyaniline-based and polythiophene-based conductive polymers. However, the present invention is not limited thereto. The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer and transports holes from the anode or the hole injection layer to the light emitting layer by using a hole transport material. Is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto. As the light emitting material, a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, and having good quantum efficiency and efficiency for fluorescence or phosphorescence is preferable. 8-hydroxyquinoline aluminum complex (Alq _3); Carbazole-based compounds; Dimerized styryl compounds; BAl q; 10-hydroxybenzoquinoline-metal compounds; Benzoxazole, benzthiazole and benzimidazole compounds; poly (P-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto. The light emitting layer may comprise a host material and a scrim material. The host material is a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. Examples of the splittable material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amines Examples of the derivative include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and ferriflantene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted arylamine A substituted or unsubstituted compound in which at least one aryl vinyl group is substituted is substituted with at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto. The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Do. Specific examples include the A1 complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer. The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has an ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A nitrogen-containing 5-membered ring derivative, and the like, but are not limited thereto. Examples of the metal complex compound include ₈ -hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphthalato) gallium, and the like But is not limited thereto. The organic light emitting device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used. In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

[Example]

Example 1: Preparation of water 1 to be converted

One -

Ethyl 2- (4-bromophenyl) acetate (30.00 g, 12.34 ol ol) was completely dissolved in dichloromethane (40 mL), and the mixture was cooled to 0 ^° C and stirred. After stirring for 10 minutes, titanium chloride (33.8 mL of IVK, 30.85 睡 ol) was slowly added dropwise. About 30 minutes The stirred solution of butyrylamine (43 mL, 30.85 mol) was slowly added dropwise. After the reaction was completed, ammonium chloride aqueous solution was added thereto and stirred for about 15 minutes. The temperature was raised to room temperature, the organic layer was extracted, and water was removed with anhydrous magnesium sulfate, followed by filtration, followed by concentration under reduced pressure. A small amount of anhydrous ethanol was added to the concentrate, stirred for 10 minutes, and filtered to obtain Compound 1-1 (29.00 g, yield: 90.00%).

MS: [M + H] < ⁺ > = 484

(29 g, 5.989 ol ol), potato hydroxides (16.8 g, 29.94 ㎎ ol) and anhydrous ethanol and water (1: 1) conical solution (580 mL ) it was stirred at 80 ^° C for 4 hours with. After completion of the reaction, the reaction mixture was cooled to 0 ^° C. HCl and filtered. The obtained solid was washed with an excess amount of water to obtain Compound 1-2 (24.4 g, yield: 99%).

MS: [M + H] < ⁺ > = 428 Step 3) Preparation of compound 1-3

Compound 1-2 (24.00 g, 5.606 mol ol) was heated and stirred with triflic acid (168 g, 112.12  ol) at 90 ^° C for 14 hours in a 1000 mL round bottom flask. After completion of the reaction, the mixture was stirred at 0 ^° C and water (336 mL) was slowly added dropwise. The resulting solid was filtered, and the resulting solid was diluted with chloroform, and water was removed with anhydrous magnesium sulfate, followed by filtration, followed by concentration under reduced pressure. The concentrate was sedimented with anhydrous ethanol to obtain Compound 1- 3 (13.2 g, yield: 60.00%).

MS: [M + H] < + > = 392

To a 500 mL round bottom flask was added compound 1-3 (10 g, 2.55 Â ol), (3,5-bis (trifluoromethyl) phenyl) boronic acid (13.8 g, 5.356  ol), tetrakis ) Was completely dissolved in tetrahydrofuran (130 mL) together with a 25% aqueous solution of palladium (0 K0.3 g, 0.0255 ㎐ ol), potassium carbonate (1.05 g, 7.65 k ol), and the mixture was heated and stirred. After the reaction was completed, the temperature was lowered to room temperature, and the organic solvent layer was collected by filtration and concentrated under reduced pressure. The concentrate was precipitated with absolute ethanol to obtain Compound 1-4 (10 g, yield: 60.00%).

MS: [M + H] < ⁺ > = 658

250 mL of round bottom flask, compound 1-4 (5.00 g, 0.759隱ol ) was stirred in a completely dissolved and ^then, at room temperature in dichloro methane (150 mL). Malononitrile (3 g, 4.556 ol ol) was added to the reaction mixture and the mixture was stirred at 0 ^° C for 10 minutes Lt; / RTI > Titanium chloride (IV) and pyridine were added and stirred at room temperature for 1 hour. After the addition of water, the mixture was stirred for 10 minutes. Then, the organic layer was collected, the water was removed with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was precipitated with methyltet-butyl ester to give Compound 1-5 (3 g, yield: 52.00%).

MS: [M + H] < ⁺ > = 754

Compound 1-5 (3.00 g, 0.397 mol) was completely dissolved in dichloromethane (90 mL) into a 250 mL round bottom flask and stirred in the upper atmosphere. 1-Bromo-2,5-pyridinedione (1.77 g, 0.994 ol ol) was added to the reaction mixture, followed by stirring for 1 hour. After completion of the reaction, the reaction mixture was filtered and washed with water and methyltet-butyl ester to give Compound 1 (2.8 g, yield: 99%).

MS: [M + H] < + > = 752 Example 2: Preparation of compound 2

To a 500 mL round bottom flask was added compound 1-3 (10 g, 2.55 ol ol), (4-cyano-3- (trifluoromethyl) phenyl) boronic acid (11.5 g, 5.355 關 ol), tetrakis Was completely dissolved in tetrahydrofuran (130 mL) together with a 25% aqueous solution of potassium carbonate (1.05 g, 7.65 ol ol) and then heated and stirred. After the reaction was completed, the temperature was lowered to room temperature, and the organic solvent layer was collected by filtration and concentrated under reduced pressure. The concentrate was precipitated with absolute ethanol to obtain Compound 2-1 (9 g, yield: 61.60%) .

MS: [M + H] < + > = 572

Compound 2 (2 g, yield: 96%) was prepared in the same manner as in Steps 5 and 6 of Example 1, except that Compound 2-1 thus prepared was used instead of Compound 1-4.

MS: [M + H] < + > = 666 Example 3: Preparation of compound 3

500 mL deunggeun the ^"Ethyl 2- (3-bromophenyl) acetate (30.00 g, 12.34瞧ol) bottom flask was cooled to 0 ^° C and then completely dissolved in dichloro methane (40 mL) and stirred. After stirring for 10 minutes, titanium chloride (33.8 mL of IVK, 30.85 mMol) was slowly added dropwise. After stirring for about 30 minutes, triethylamine (43 mL, 30.85 mMol) was slowly added dropwise. After the reaction was completed, ammonium chloride aqueous solution was added thereto and stirred for about 15 minutes. The temperature was raised to room temperature, the organic layer was extracted, and the water was removed with anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. A small amount of anhydrous ethanol was added to the concentrate, stirred for 10 minutes, and then filtered to obtain Compound 3-1 (29.00 g, yield: 90.00%).

MS: [M + H] < ⁺ > = 484

To a 1000 mL round bottom flask was added a mixed solution of compound 3-1 (29 g, 5.989  ol), potassium hydroxide (16.8 g, 29.94 mol), and anhydrous ethanol and water (1: mL) at 80 [ ^deg.] C for 4 hours. After the reaction was completed, the reaction mixture was cooled to 0 ^° C. HCl and then filtered. The obtained solid was washed with an excess amount of water to obtain Compound 3-2 (24.4 g, yield: 99%).

MS: [M + H] < + > = 428

3-2

Compound 3-2 (24.00 g, 5.606  ol) was heated and stirred with Triflic acid (168 g, 112.12  ol) at 90 ^° C for 14 hours in a 1000 mL round bottom flask. After completion of the reaction, the mixture was cooled to 0 ^° C and water (336 mL) was slowly added dropwise. The resulting solid was filtered, and the resulting solid was diluted with chloroform, and water was removed with anhydrous magnesium sulfate, followed by filtration, followed by concentration under reduced pressure. The concentrate was sedimented with anhydrous ethanol to obtain Compound 3- 3- (13.2 g, yield: 60.00%). MS: [M + H] < ⁺ > = 392

Compound 3 (2.5 g, yield: 9900) was prepared in the same manner as in steps 4 to 6 of Example 1, except that Compound 3-3 was used instead of Compound 1-3.

S: [M + H] < ⁺ > = 752 Example 4: Preparation of compound 4

To a 500 mL round bottom flask was added compound 3-3 (10 g, 2.55  ol), (4-cyano-3- (trifluoromethyl) phenyl) boronic acid (11.5 g, 5.355  ol), tetrakis Was completely dissolved in tetrahydrofuran (130 mL) together with a 25% aqueous solution of potassium carbonate (1.05 g, 7.65 mmol), potassium carbonate (0.35 g, 0.0255 ol ol) and the mixture was heated and stirred. After the completion of the reaction, the temperature was lowered to room temperature, and the organic solvent layer was collected by filtration and concentrated under reduced pressure. The concentrate was precipitated with absolute ethanol to obtain Compound 4-1 (11 g, yield: 75.3%). MS: [M + H] < ⁺ > = 572

Compound 4 (3 g, yield: 96%) was prepared in the same manner as in Steps 5 and 6 of Example 1, except that Compound 4-1 prepared above was used instead of Compound 1-4.

MS: [M + H] < + > = 666 Example 5: Preparation of compound 5

5-1

To a 500 mL round-bottomed flask was dissolved completely ethyl 2- (2-bromophenyl) acetate (30.00 g, 12.34 mmol) in dichloromethane (40 mL), then cooled to 0 ^° C and stirred. After 30 minutes of stirring, triethylamine (43 mL, 30.85 ol ol) was slowly added dropwise to the reaction mixture, followed by the addition of aqueous ammonium chloride solution The mixture was stirred for about 15 minutes, the temperature was raised to room temperature, and the organic layer was extracted with anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure. A small amount of anhydrous ethanol was added to the concentrate, stirred for 10 minutes, 5-1 (20.00 g, yield: 60.00%).

MS: [M + H] < ⁺ > = 484

To a 1000 mL round bottom flask was added a solution of compound 5-1 (20 g, 4.130  ol), potassium hydroxide (11.59 g, 20.65  ol), and anhydrous ethane in water (1: mL) at 80 [ ^deg.] C for 4 hours. After the reaction was completed, the reaction was quenched at 0 ^° C. HCl and then filtered. The resulting solid was washed with an excess amount of water to obtain Compound 5-2 (17.0 g, yield: 91%).

MS: [M + H] < ⁺ > = 428

Compound 5-2 (17.00 g, 3.971 ol) was heated and stirred with triflic acid (119 g, 79.29  ol) at 90 ^° C for 14 hours. After completion of the reaction, the mixture was stirred at 0 ^° C and water (336 mL) was slowly added dropwise. The resulting solid was filtered, and the obtained solid was diluted with chloroform, and water was removed with anhydrous magnesium sulfate, followed by filtration, followed by concentration under reduced pressure. The concentrate was sedimented with anhydrous ethanol to obtain Compound 5-3 (10 g, yield: 64.00%). MS: Preparation of [M + H] < ⁺ > = 392

Compound 5 (2.6 g, yield: 99%) was prepared in the same manner as in steps 4 to 6 of Example 1, except that Compound 5-3 was used instead of Compound 1-3.

MS: [M + H] < ⁺ > = 752 Example 6: Preparation of compound 6

To a 500 mL round bottom flask was charged 5-3 (10 g, 2.55 eq), (4-cyano-3- (trifluoromeloxy) phenyl) boronic acid (12.37 g, 5.357  ol), tetrakis Was completely dissolved in tetrahydrofuran (130 mL) together with a 25% aqueous solution of potassium carbonate (1.05 g, 7.65 mmol), followed by heating and stirring. After the reaction is finished, The temperature was lowered and the organic solvent layer was collected by filtration and concentrated under reduced pressure. The concentrate was precipitated with absolute ethanol to obtain Compound 6-1 (7 g, yield: 45.4%).

MS: [M + H] < + > = 604 Preparation

6

Compound 6 (2.2 g, yield: 95%) was prepared in the same manner as in steps 5 and 6 of Example 1, except that Compound 6-1 was used instead of Compound 1-4.

MS: [M + H] < ⁺ > = 698

[Experimental Example]

Experimental Example 1-1

ITOdndium Tin Oxide) was put into distilled water dissolved in detergent and ultrasonically cleaned. As the detergent, Decon ™ C0N705 product of Fischer Co. was used and distilled water which was secondly filtered with 0.22 μη sterilizing filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone and methanol for 10 minutes, dried, and then transported to a plasma cleaner. Also, The substrate was cleaned using plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator. The following HT-A compound and the compound 1 prepared in the previous example were thermally vacuum deposited at a weight ratio of 95: 5 to a thickness of 100 A on the ITO transparent electrode prepared above to form a hole injection layer. Only the HT-A compound shown below was deposited on the hole injection layer to a thickness of 1100 A to form a purified water-feeding solution. The following EB-A compound was thermally vacuum-deposited on the hole transport layer to a thickness of 50 A to form an electron blocking layer. The following BH-A compound and the following BD-A compound were vacuum deposited on the electron blocking layer at a weight ratio of 96: 4 to a thickness of 200A to form a light emitting layer. The following ET-A compound and the following Liq compound were thermally vacuum-deposited on the light emitting layer at a weight ratio of 1: 1 to a thickness of 360A to form an electron transport layer. The following Liq compound was vacuum-deposited on the electron transport layer to a thickness of 5 A to form an electron injection layer. Magnesium and silver were sequentially deposited on the electron injection layer at a weight ratio of 10: 1 to a thickness of 220 A and aluminum to a thickness of 1000 A

HT-A EB-A BH-A

Experimental Examples 1-2 to 1-6

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compounds described in the following Table 1 were used instead of the Compound 1 in Experimental Example 1-1. Comparative Experimental Example 1-1

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that only HAT-CN compound shown below was used as the hole injection layer in Experimental Example 1-1.

HAT-CN Comparative Experimental Example 1-2

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the hole injection layer was formed without any doping instead of Compound 1 in Experimental Example 1-1. Comparative Experimental Example 1-3

Except that Compound A was used instead of Compound 1 in Experimental Example 1-1.

A Comparative Experimental Examples 1-4

An organic light emitting device was prepared in the same manner as in Experimental Example 1-1, except that Compound B was used instead of Compound 1.

B The driving voltage and efficiency of the organic light emitting devices manufactured in Experimental Examples 1-1 to 1-6 and Comparative Experimental Examples 1-1 to 1-4 are shown in Table 1 below. At this time, the driving voltage and the efficiency were measured by applying a current density of 10 mA / cm < ^{2 &} gt ;.

[Table 1]

Experimental Example 2-1

The glass substrate coated with ITO (indium tin oxide) thickness of Ι and ΟΟΟΑ was put into distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then washed with a plasma cleaner Lt; / RTI > Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator. The following HAT-CN compound was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 50 A to form a hole injection layer. The following NPB compound was vacuum deposited on the hole injection layer to a thickness of 100 A to form a first hole transport layer. The following EB-B compound was vacuum-deposited on the first hole transporting layer to a thickness of 100 A to form an electron blocking layer. The following YGH-A compound, the following YGH-B compound, and the following YGD compound were vacuum deposited on the first electron blocking layer at a weight ratio of 2: 2: 1 to a thickness of 400A to form a first light emitting layer. The following ET-B compound was vacuum-deposited on the emissive layer to a thickness of 250 A to form a first electron transporting layer. An N-type charge generation layer was formed by vacuum depositing the following NCG compound and Li (Li thium) on the Ge electron transport layer at a weight ratio of 50: 1 to a thickness of 100A. On the N-type charge generation layer, the following HT-A compound was formed to a thickness of 100A, and Compound 1 was doped with a doping concentration of 30% by weight to form a P-type charge generation layer. Only the following HT-A compound was vacuum-deposited on the P-type charge generation layer to a thickness of 800 A to form a second hole transporting layer. The following BH-B compound and the following BD-B compound were vacuum deposited on the second hole transporting layer at a weight ratio of 96: 4 to a thickness of 250 A to form a second light emitting layer. On the second light-emitting layer, the following ET-A compound and the following Li q compound were thermally vacuum deposited at a weight ratio of 1: 1 to a thickness of 300A to form a second electron transporting layer. LiF (Li.sub.3Si.sub.2Fluoride) was deposited on the electron transport layer to a thickness of 10A and aluminum to a thickness of 800A to form a cathode. Thus, an organic light emitting device was manufactured.

NCG BH-B BD-B Experimental Examples 2-2 to 2-6

An organic light emitting device was prepared in the same manner as in Experimental Example 2-1, except that the compound shown in the following Table 2 was used instead of the Compound 1 in Experimental Example 2-1. Comparative Experimental Examples 2-1 to 2-3

An organic light emitting device was prepared in the same manner as in Experimental Example 2-1 except that the compounds described in the following Table 2 were used instead of the compound 1 in Experimental Example 2-1 . The HAT-CN compound, A compound and B compound, which are the compounds shown in Table 2, are the same as the compounds described in Table 1 above. Table 2 shows the driving voltage and efficiency of the organic light emitting devices manufactured in Experimental Examples 2-1 to 2-6 and Comparative Examples 2-1 to 2-3. At this time, the driving voltage and the efficiency were measured by applying a current density of 10 mA / cm < ^{2 &} gt ;.

[Table 2]

DESCRIPTION OF REFERENCE NUMERALS

1: substrate 2:

ᅳ 1

3: luminescent layer 4:

ᄆ ᄀ

5: hole injection layer 6: high

3 ο 丁^" Γ

7: light emitting layer 8: electron transporting layer

9: electronic jersey dance 10 electron injection layer

11 First hole transport layer 12 U Light emitting layer

13 < / RTI > U electron transport layer 14 < RTI ID =

15 P-type charge generation layer 16 charge ² hole transport

17 Second light emitting layer 18 Crab 2 Electron transport layer

Claims

[Claims]

[Claim 1]

A compound represented by the following formula (1):

In Formula 1,

Ri and R ₂ are each independently selected from the group consisting of hydrogen, substituted or unsubstituted d-60 alkyl, substituted or unsubstituted d- ₆₀ alkoxy, substituted or unsubstituted d- ₆₀ haloalkyl, substituted or unsubstituted C JO halo c ₂ containing ₆₀ aryl, or a substituted or unsubstituted 0, N, Si and S 1 out of over-the-alkoxy, halogen, cyano, tri (d-60 alkyl) silyl, a substituted or unsubstituted C ₆ ₆₀ Heteroaryl,

Each independently represent hydrogen, deuterium, substituted or unsubstituted d-60 alkyl, substituted or unsubstituted ( ₆₀ alkoxy, substituted or unsubstituted haloalkyl, substituted or unsubstituted d-60 haloalkoxy, halogen (C-60 alkyl) silyl or a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl containing at least one of O, N, Si and S,

^■ Ar is a C ₆ - _60, and heteroaryl, wherein the C ₆ - - ₆₀ aryl, or C ₂ - ₆₀ aryl, or 0, N, C _2, including one or more of Si and S ₆₀ heteroaryl, substituted Or substituted or unsubstituted ( ₆₀ alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted ( ₆₀ haloalkyl, substituted or unsubstituted d-60 haloalkoxy, halogen, cyano, and tri Lt; RTI ID = 0.0 > 1 < / RTI > to 5 substituents each selected from the group consisting of

[Claim 2]

The method according to claim 1,

Ri and < RTI ID = 0.0 > 3 < / RTI > are each independently cyano or 2,3,5,6-tetrafluoro- 4-cyanophenyl,

compound.

[Claim 3]

In that U section,

And R < ₄ > are each independently hydrogen or deuterium.

Claim 4

The method according to claim 1,

The compound represented by the general formula (1)

compound:

[Formula 1-3]

In Formulas 1-1-2, 1-3 and 1-4,

And Ar are as defined in claim 1.

[Claim 5]

The method according to claim 1,

Ar is phenyl, wherein said phenyl is substituted or unsubstituted d-so alkyl, substituted or unsubstituted d-60 alkoxy, substituted or unsubstituted d-60 haloalkyl, substituted or unsubstituted CO haloalkoxyhalogen, Each of which is optionally substituted with one to five substituents each independently selected from the group consisting of halogen, cyano, and tri (d-60 alkyl) silyl. [Claim 6]

In Item 1,

Ar is phenyl, wherein said phenyl is optionally substituted with one to five substituents each selected from the group consisting of fluoro, trifluoromethyl, trifluoromethyl, and cyano;

compound. 7.

In Item 1,

Ar is any one selected from the group consisting of:

The method according to claim 1,

The compound represented by Formula 1 is any one selected from the group consisting of

50

51 _{/: /} O12 ₀ S _8Z - ₀₆ S _Z AV

53

54

55

[Claim 9]

A first electrode; A second electrode facing the first electrode; And at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers includes the compound according to any one of claims 1 to 8 The organic light-emitting device.

Claim 10

10. The method of claim 9,

The organic compound layer may include a hole injection layer, and the hole injection layer may be formed of the compound alone or may be doped with the compound

Organic light emitting device. Claim 11

10. The method of claim 9,

Wherein the organic layer comprises a doped hole transport layer, the doped Wherein the hole transporting layer is formed by doping the hole transporting material with the compound.

[12]

In Item 9,

A first stack that emits light of a first color, a second stack that emits light of a second color, and a second stack that emits light of a first color and a second stack that emit light of a first color, A charge generation layer is formed,

Wherein the charge generating layer comprises an N-type charge generating layer adjacent to the first stack and a P-type charge generating layer adjacent to the second stack,

Wherein the organic material layer constitutes the P-type charge generation layer and the P-type charge generation layer comprises the compound alone or is doped with the compound.

Organic light emitting device.

[13]

10. The method of claim 9,

A first stack for emitting light of a first color and a second stack for emitting light of a second color are provided between the first electrode and the second electrode, A charge generation layer is formed,

Wherein the organic material layer constitutes the P-type charge generation layer, and the P-type charge generation layer comprises a hole transport material doped with the compound,

Organic light emitting device.

14.

In paragraph 9, Wherein the organic light emitting device further comprises one or more layers selected from the group consisting of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting electron injecting layer, an electron blocking layer and a hole blocking layer.

Organic light emitting device.