WO2019013487A1

WO2019013487A1 - Novel compound and organic light-emitting device using same

Info

Publication number: WO2019013487A1
Application number: PCT/KR2018/007579
Authority: WO
Inventors: 강민영; 문정욱; 박태윤; 이정하; 정민우; 조성미; 채미영
Original assignee: 주식회사 엘지화학
Priority date: 2017-07-12
Filing date: 2018-07-04
Publication date: 2019-01-17
Also published as: CN110536887B; KR20190007257A; KR102078301B1; CN110536887A

Abstract

The present invention provides a novel compound and an organic light-emitting device using same.

Description

Title of the Invention

Novel compounds and organic light emitting devices using the same

TECHNICAL FIELD

The present application claims the benefit of priority based on Korean Patent Application No. 10-201, 0088464, filed on July 12, 2017, and all contents disclosed in the relevant Korean patent application are incorporated herein by reference, As shown in FIG. The present invention relates to a novel compound and an organic light emitting device comprising the same.

TECHNICAL BACKGROUND OF THE INVENTION

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 a wide viewing angle, excellent contrast, fast response time, excellent characteristics of brightness, driving voltage, and response speed, and much research is proceeding. 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. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multilayer structure composed of different materials. 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 such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, and an exciton is formed when the injected holes and electrons meet each other. 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 or 2:

In the above Formulas 1 and 2,

X is O or S,

Li and L ₂ are each independently a single bond; Substituted or unsubstituted C ₆ - ₆₀ Arylene; Or a substituted or unsubstituted C ₂ - ₆₀ heteroarylene containing at least one heteroatom selected from the group consisting of O, N, Si and S,

Ar is a substituted or unsubstituted C ₆ - ₆₀ aryl; Or substituted or unsubstituted C ₂ -C ₆ heteroaryl containing 1 to 3 heteroatoms selected from the group consisting of N, O and S,

Each independently represent hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d-60 alkyl; Substituted or unsubstituted d-60 haloalkyl; Substituted or unsubstituted ₆₀ alkoxy; Substituted or unsubstituted haloalkoxy; Substituted or unsubstituted C ₃ - ₆₀ cycloalkyl; A substituted or unsubstituted C ₂ - 60 alkenyl; Substituted or unsubstituted C ₆ -C ₆₀ aryl; Substituted or unsubstituted C ₆ -C ₆₀ aryloxy; Or substituted or unsubstituted C ₂ -C ₆₀ heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S,

al to a5 are each independently an integer of 0 to 2; The present invention also provides a plasma display panel comprising: a first electrode; A second electrode arranged opposite to the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound represented by Formula 1 or 2, to provide. 【Effects of the Invention】

The compound represented by the above formula (1) or (2) can be used as a material for the organic material layer of the organic light emitting device, and can improve the efficiency, the driving voltage and / or the lifetime of the organic light emitting device. 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.

DETAILED DESCRIPTION OF THE INVENTION Hereinafter, the present invention will be described in detail in order to facilitate understanding of the present invention.

Means a bond connected to another substituent, and a single bond means a case where no separate atom exists in the moiety represented by L < ₂ >. As used herein, the term " substituted or unsubstituted " A halogen group; Cyano; 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 heteroaryl 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 . For example, " a substituent to which at least two substituents are connected " may be a biphenyl group. That is, the biphenyl group may be an aryl group, or 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, the compound may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group means that the oxygen of the ester group is a straight chain, branched chain or cyclic alkyl group having 1 to 25 carbon atoms, Lt; / RTI > may be substituted with an aryl group having 1 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, One

In the present specification, the number of carbon atoms in the imide group is not particularly limited and preferably 1 to 25 carbon atoms. Specifically,

The compound

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 phenylsilyl group and the like But is 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 or iodine. In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. Work According to the embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another aspect and an embodiment, the number of carbon atoms of the alkyl group is 1 to 6. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, Propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, n-heptyl, 1-methylnucleosilyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 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, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like. In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. 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, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3- 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, Cycloheptyl, cyclooctyl, and the like, 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. When the fluorenyl group is substituted,

And the like. However, the present invention is not limited thereto. In the present specification, the heteroaryl is a heteroaryl containing at least one of 0, N, Si and S as a hetero atom. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heteroaryl include a thiophene group, a furane group, a pyrimidyl group, a triazine group, a triazo group, a pyrimidyl group, a pyrimidyl group, a thiazolyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, a pyrazinyl 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, A benzothiazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthrene group, a phenanthroline group, a thiazole group, a thiophene group, An isoxazolyl group, an oxadiazolyl group, A thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is 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 heteroaryl described above. 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 this specification, the description of the above-mentioned heteroaryl can be applied except that the heteroarylene is a 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 heteroaryl described above can be applied, except that the heterocycle is not monovalent and two substituents are bonded to each other. Meanwhile, the present invention provides a compound represented by the above formula (1) or (2). In the above Formulas 1 and 2, Li and L ₂ are each independently a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrene Substituted or unsubstituted thiophene, thienylene, substituted or unsubstituted anthracenylene, substituted or unsubstituted fluoranthenylene, substituted or unsubstituted triphenylenylene, substituted or unsubstituted pyrenylene, substituted or unsubstituted carbazolylene, Substituted or unsubstituted fluorenylenes, substituted or unsubstituted fluorenylenes, or substituted or unsubstituted spiro-fluorenylenes. For example, and L < ₂ > may each independently be a single bond, or phenylene. Also, Ar is a substituted or unsubstituted C ₆ - ₂₀ aryl; Or a substituted or unsubstituted C ₂ containing 1 to 3 hetero atoms 0 or S - ₂₀ may be a heteroaryl. For example, each Ar may be independently selected from the group consisting of:

In the above,

Y is O, S, or CZ ₄ Z ₅ ,

Z: each independently represent hydrogen; Hydrogenation; halogen; Cyano; Nitro; Amino; d- ₂₀ alkyl; d- ₂₀ haloalkyl; C ₆ - ₂₀ aryl; ₂₀ is a heteroaryl, - C ₂ containing zero or one or more heteroatoms of S

n1 to n3 each independently represent an integer of 0 to 3; Each independently represent hydrogen, deuterium, phenyl, or biphenyl,

Z ₄ and Z ₅ are each independently methyl or phenyl,

n1 to n3 each independently represent 0, 1, or 2; Specifically, for example, Ar may be any one selected from the group consisting of:

R ₁ to R ₅ are each independently hydrogen; heavy hydrogen; halogen; Cyano;

Ci-QQ alkyl; Or C ₆ - ₂₀ may be an aryl group.

For example, each of R 1 to R 4 is independently hydrogen, deuterium, halogen, Cyano, methyl, or phenyl, and al to a5 may each independently be 0 or 1. Specifically, for example, ¾ to R ₅ may be hydrogen. In this case, the number of al indicates the number of al. When al is 2 or more, 2 or more may be the same or different from each other. The description of al to a5 and n1 to n3 can be understood with reference to the description of al and the structure of the above formula (1) or (2). On the other hand, the compound may be represented by one of the following formulas 1-1 to 1-4 and 2-1 to 2-4:

[Chemical Formula 1-3] [Chemical Formula 1-4]

[Formula 2-1] [Formula 2-2]

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

X and Ar are as defined in the above formulas (1) and (2). For example, the compound may be any one from the group consisting of the following compounds:

£ 1

.SZ.OO / 8lOra¾ / X3d .81-Π0 / 6Τ0Ζ OAV

Z.SZ.00 / 8T0ZaM / X3d Z.817C10 / 610Z OAV

The compounds represented by the above general formulas (1) and (2) have a structure in which an amino group is linked to the 4-position of fluorene, and the organic light emitting element employing the compound has a structure in which a compound having a structure in which amino groups are connected to other positions of fluorene Compared to a light emitting device, it has a high efficiency, a low driving voltage, a high brightness and a long life have. Meanwhile, the compound represented by the formula (1) or (2) can be prepared, for example, according to the following method. The above production method can be more specific in the production example to be described later.

1-a 1-b In Formula 1, L ₂ , Ar, and X are as defined above.

The above reaction may include a step of counteracting the compound represented by the formula (1-a) and the compound represented by the formula (1-b) to prepare the compound represented by the formula (1). Preferably, the reaction is carried out in the presence of a palladium catalyst and a base as an amine substituent, and the reaction time for the amine substitution reaction (for example, X 'is halogen) can be varied as is known in the art. The above production method can be more specific in the production example to be described later. The compound represented by Formula 2 may be prepared by appropriately substituting the starting material according to the structure of the compound to be prepared with reference to the above-mentioned Hanwoi 1. Meanwhile, the present invention provides an organic light emitting device comprising a compound represented by the above formula (1) or (2). In one embodiment, the present invention provides a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one layer provided between the first electrode and the second electrode and an organic layer, wherein at least one of the organic layers includes a compound represented by Formula 1 or 2, to provide. 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 an organic material layer. 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 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 further includes, as an organic material layer, a hole injection layer and a hole transporting layer between the first electrode and the light emitting layer, and an electron transporting layer and an electron injecting layer between the light emitting layer and the ground electrode . &Lt; / RTI > However, the structure of the organic light emitting device is not limited thereto, and may include fewer or more organic layers. The organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, at least one organic layer, 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 an anode, one or more organic compound layers 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 or 2 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 or 2 may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting layer. The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one of the organic layers includes the compound represented by Formula 1 or 2. 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 an alloy thereof may be formed on the substrate by a PVD (physi cal vapor deposition) method such as a sputtering method or an e-beam evaporation method Depositing a cathode, forming an anode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer on the anode, and depositing a material usable as a cathode 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 or 2 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, ink jet printing, screen printing, spraying, 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, it is preferable that the hole injection is normally performed smoothly into the organic material layer A material having a large work function is preferable. 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 (II), 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] (PEDOT), polypyrrole and polyaniline, no. 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 magnes, calcium, sodium, potassium, titanium, indium, yttrium, lithium, 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 migration of the exciton to the electron injection layer or the electron injecting material and is also excellent in the ability to form a thin film is preferred. The HOffi high occupied molecular orbital of the hole injecting material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer . Specific examples of the hole injecting material include organic materials such as porphyrin, oligothiophene, arylamine-based organic materials, quinacridone-based tetraphenylene-based organic materials, quinacridone-based organic materials, perylene ) Organic materials, anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto. The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer. The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, But is not limited thereto. The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Poly (P-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto. The light emitting layer may include a host material and a scrim material as described above. The host material may further include 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 dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and 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 is substituted or unsubstituted. 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 receives electrons from the electron-injecting layer and reaches the light-emitting layer As an electron transporting material, a material having high mobility for electrons and electrons is suitable as a material capable of injecting electrons from a cathode well and transferring it to a light emitting layer. 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, it is serch, barium, foxtail, ytterbium and samarium, in each case followed by an aluminum layer or silver bush. 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. It is preferable to use a compound which prevents migration to the layer and is excellent in the ability to form a thin film. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, Perylenetetracarboxylic acid, preorenylidene methane, anthrone, and derivatives thereof, metal complex compounds and nitrogen-containing 5-membered ring derivatives, 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 And may be a back-light-emitting type or a both-side light-emitting type. The compound represented by Formula 1 or 2 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device. The preparation of the compound represented by the above formula (1) or (2) and the organic light emitting device comprising the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto. Manufacturing example

A

Step 1) Preparation of Compound A-1

After dissolving ethyl 2-bromobenzoate (15 g, 65.5 mmol) and (2-methoxyphenyl) boronic acid (10.5 g, 68.8 mmol) in tetrahydrofuran (200 ml), a 2M aqueous potassium carbonate solution . K ₂ CO ₃ ) (65 ml, 130 mmol) was added Tetrakistriphenylphosphine palladium into the Pinot _{_{[Pd (PPh 3) 4]}} (760 mg, 1 mol%) was then stirred for 6 hours under reflux. The temperature was lowered to room temperature, the water layer was separated, and the organic layer was further washed with water once more to separate the layers. Anhydrous magnesium sulfate was added to the collected organic layer, followed by slurry filtration and concentration under reduced pressure. The compound in oil state was separated through a silica column using a combination of nucleic acid and ethyl acetate to prepare 13.6 g of compound A-K (yield 8) as a white solid. Step 2) Preparation of Compound A-2

Compound Al (16 g, 62 mmol) was added to a solution of anhydrous tetrahydrofuran (175 ml), then the solution was lowered in the ice using an icebath, and a solution of 1 M methylmagnesium bromide in tetrahydrofuran (190 ml) And the mixture was stirred at room temperature for 5 hours. After completion of the addition of water, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained compound was separated through a silica column using a combination of a nucleic acid and ethyl acetate to obtain objective compound A-2 (13.0 g, yield 86%). Step 3) Preparation of Compound A-3

Compound A-2 (15 g, 62  ol) was added to 150 mL of acetic acid, and then 3 mL of concentrated sulfuric acid was added. The mixture was heated at 60 ^° C and stirred for 3 hours. When the reaction was completed, the solid precipitated at room temperature and filtered. The filtered solid was dissolved in ethyl acetate and washed with saturated sodium bicarbonate aqueous solution. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The screen by the addition of ethanol and the nucleic acid in a concentrated compound to precipitate a solid after the slurry (to prepare a 10.1g, yield 73¾. Step 4) and filtered to ^'the desired compound A-3 Preparation of Compound A-4

Compound A-3 (13.8 g, 61.5 mmol) was added to tetrahydrofuran (140 mL), the temperature was lowered to -70 ^° C, 1.6M n-butyllithium nucleic acid solution (44 mL) was slowly added and stirred for 1 hour. Triisopropyl borate (12.3, 61.7 ㏖ ol) was added dropwise to the mixture, and the mixture was stirred at room temperature for 5 hours. 2M hydrochloric acid was added to the obtained filtrate, and the mixture was stirred at room temperature for 3 hours. A mixture Extracted with ethyl acetate, the organic layer was washed twice with water, dried over anhydrous sodium sulfate and the solvent was concentrated under reduced pressure. The concentrated compound was slurried with nucleic acid and ethanol, and the product was filtered to obtain the desired compound A-4U (1.6 g, yield: 70.4 g). Step 5) Preparation of compound A-5

Compound A-4 (15 g, 56 mmoO) and 1-bromo-2-fluoro-3-iodobenzene (16.8 g, 56  ol) were dispersed in tetrahydrofuran (150 ml) _{_{aq. K 2 C0 3) (}} 56 ml, 112面ol) was added and tetrakis triphenyl phosphino palladium [Pd (PPh ₃₎ _4] a (after inserting the 650 mg, 1 mol¾0 was refluxed and stirred for 6 hours at room temperature The organic layer was washed with water once more to separate the water layer, and the organic layer was separated. The organic layer was combined with anhydrous magnesium sulfate for slurrying, followed by filtration and concentration under reduced pressure. The resulting compound was dissolved in ethyl acetate and ethanol The objective compound A-5 (15.7 g, yield 77%) was prepared by recrystallization. Step 6) Preparation of Compound A-6

Compound A-5 (15 g, 37.8 mmol) was added to 150 mL of dichloromethane, the temperature of the solution was reduced to -70 ^° C, 50 mL of 1M boron tribromodichloromethane solution was slowly added dropwise, And the mixture was stirred for 5 hours. After completion of the reaction, water was added to the residue, extracted with dichloromethane, and the organic layer was washed with water. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting concentrate was slurried with a small amount of ethyl acetate and then filtered to obtain the target compound A-6 (12 g, yield 83%). Step 7) Preparation of intermediate A

Compound A-6C (24 g, 63 mmol) was diluted in 120 mL of N-methyl-2-pyrrolidone and potassium carbonate (17.3 g, 63 mmol) was added thereto and the mixture was poured into 14 CTC. After about 1 hour, the reaction mixture was cooled to room temperature and slowly added to 1.2 L of water. The precipitated solid was filtered, dissolved in tetrahydrofuran, treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The concentrated compound was dissolved in a small amount of tetrahydrofuran Slurried with an excess of nucleic acid and filtered. To purify the filtered compound, 14.7 g of intermediate M, 65% yield, MS: [M + H] < ⁺ > = 364) was prepared by separating through a silica column with nucleic acid and ethyl acetate.

Intermediate A In the synthesis example of the compound A-5 of the production example A, except that 1-bromo-3-fluoro-2-iodobenzene was used instead of 1-bromo-2- A similar preparation was conducted in the same manner as in Synthesis Example A.

Step 1) Preparation of Compound C-1

The compound methyl 2-bromo-5-chlorobenzoate (25 g, 100 mmol) and di benzo [b, d] furan-4-yl boronic acid (21.2 g, 100 mmol)

1, the compound C-1 (27 g, 80%) was prepared. Step 2) Preparation of compound C-2

Compound C-2 (18 g, 7) was prepared in the same manner as in the preparation example of Compound A-2, using Compound C-1 (25 g, 74 隱 ol). Step 3) Preparation of intermediate C

(10.4 g, 73%, MS: [M + H] < + > = 319) was prepared in the same manner as in the preparation example of Compound A-3 using Compound C-2 (15 g, 44.5  ol) .

Step 1) Preparation of Compound 1-1

(9.8 g, 58  ol) was added to 200 mL of toluene to dissolve the intermediate A (20 g, 55 mmol) and [1,1'-biphenyl] -4-amine, and sodium tertiary- 110 mmol) was added and warmed. And palladium (0.3 g, 1 mol%) of bis (tritiated-butylphosphine) was added thereto, followed by reflux stirring for 3 hours. When the reaction was completed, the mixture was concentrated under reduced pressure, and the concentrated product was dissolved in chloroform (300 mL) and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the filtrate was distilled off under reduced pressure. The concentrated compound was purified by silica column chromatography to obtain Compound 1-1 (18.1 g, yield 73%). Step 2) Preparation of Compound 1-2

A solution of 4-bromo-9,9-dimethyl-9H-fluorene (20 g, 73.2 mmol) and (4-chlorophenyl) boronic acid (12.6 g, 80.5 mmol) in tetrahydrofuran then, a 2M potassium carbonate aqueous solution (aq. K ₂ C0 ₃₎ was added (73 ml, 143醒ol) and tetrakis triphenyl phosphino palladium _{_{[Pd (PPh 3) 4]}} (850 mg, 1 η) 1¾) And the mixture was refluxed with stirring for 6 hours. The temperature was lowered to room temperature, the water bug was separated, and the organic layer was further washed once more with water to separate the organic layer. Anhydrous magnesium sulfate was added to the collected organic layer, followed by slurry filtration and concentration under reduced pressure. The resulting compound was recrystallized from ethanol to obtain Compound 1-2 (18.0 g, 81%). Step 3) Preparation of Compound 1

The compound 1-1 (20 g, 44 瞧 ol) and the compound 1-2 (14.2 g, 46.5 匪 ol) were dissolved in 200 mL of xylene and added with sodium tertiary-butoxide (18.8 g, 88.6 mmol) Lt; / RTI > (Tris (tert-butylphosphine) palladium (0.23 g, 1 mol%) was added thereto, followed by stirring under reflux for 8 hours. When the reaction was completed, the xylene was concentrated under reduced pressure, and the concentrated residue was dissolved in 400 mL of chloroform and washed twice with water. The organic layer was separated, and anhydrous magnesium sulfate was added and stirred, followed by filtration, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica column chromatography to obtain Compound 1 (23.4 g, yield 74%, MS: [M + H] ⁺ = 720).

Step 1) Preparation of compound 2-1

Using the intermediate B, an experiment was conducted in the same manner as in the production example of the compound 1-1 Compound 2-1 was prepared. Step 2) Preparation of compound 2

Compound 2-1 was used in the same manner as in the preparation of Compound 1 to prepare Compound 2. (MS: [M + H] < ⁺ > = 644)

Step 3 1) Preparation of Compound 3-1

The same procedure as in the preparation example 1-2 was conducted using 4-bromoaniline (25 g, 145 mmol) and dibenzo [b, d] furan-4-ylboronic acid (30.8 g, Compound 3-1 (25.6 g, 68%) was prepared. Step 2) Preparation of compound 3-2

Compound 3-2 (30.5 g, 73 W) was prepared using Compound 3-1 (20 g, 77 mmol) and Intermediate C (24.6 g, 77 mmol) Preparation of Compound 3 Preparation of Compound 1-1 Using Compound 3-2 (18 g, 33 mmol) and compound 4-bromo-9,9-dimethyl-9H-fluorene (9.1 g, 33 mmol) 3 (18.3 g, 75%, MS: [M + H] < ⁺ > = 734). Example 1

The glass substrate coated with thin ITO (indium tin oxide) film with a thickness of 1, 300 A was washed with ultrasonic waves in distilled water containing detergent. As a detergent, a product of Fischer Co. was used. Distilled water, which was filtered by a filter (Fi l ter) manufactured by Mi 1 1 ipore Co., was used as distilled water. IIT0 was washed for 30 minutes, then repeated twice with distilled water, and sonicated 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 transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator. The following HI-1 compound was prepared on the thus prepared ITO transparent electrode

500A to form a hole injection layer. The HT-1 compound was thermally vacuum-deposited on the hole injection layer to form a hole-filling solution. The compound 1 synthesized in Example 1 was vacuum-deposited on the HT-1 vapor deposition layer to a thickness of 100 A to form an electron blocking layer . Subsequently, BH and BD were vacuum deposited on the electron blocking layer at a weight ratio of 25: 1 at a film thickness of 300 A to form a light emitting layer.

The compound Eq and Liq were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injecting and transporting layer having a thickness of 300A. Lithium fluoride (LiF) and aluminum having a thickness of 2000 A were sequentially deposited on the electron injection and transport layer to a thickness of 12 A to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 A / sec, the lithium fluoride at the cathode was maintained at 0.3 A / sec, and the deposition rate at the aluminum was maintained at 2 A / sec. - ⁷ to 5 x 10 ^& lt ^{; -8} > torr. Example 2

An organic light emitting device was prepared in the same manner as in Example 1, except that the compound 2 of Preparation Example 5 was used instead of the compound 1 of Production Example 4. Example 6

An organic light emitting device was prepared in the same manner as in Example 1, except that the compound 3 of Preparation Example 6 was used instead of the compound 1 of Production Example 4. Comparative Examples 1 and 2

And that the following compounds D and E were used in place of the compound 1 of Production Example 4.

[Experimental Example 1]

The current, voltage, efficiency, color coordinates and lifetime of the organic light-emitting device fabricated in Examples 1 to 3 and Comparative Examples 1 and 2 were measured, and the results are shown in Table 1 below. In this case, T95 means the time required for the luminance to decrease from the initial luminance (100o n t) to 95¾.

[Table 1]

Example 4

The following HI-1 compound was thermally vacuum-deposited on the ITO transparent electrode prepared in the same manner as in Example 1 to a thickness of 500 A to form a hole injection layer. The HT-2 compound was thermally vacuum-deposited on the hole injection layer to a thickness of 800 A and the HT-3 compound was sequentially vacuum-deposited to a thickness of 500 A to form a hole transport layer. Subsequently, Compound 1 and GH1 of Preparation Example 4 were vapor-deposited at a weight ratio of 50% on the HT-3 vapor-deposited film by simultaneous evaporation to a thickness of 400 A, and the phosphorescent dopant GD-1 was co- .

An ET-2 material was vacuum-deposited on the light-emitting layer to a thickness of 50 A to form a hole blocking layer. An ET-3 material and LiQ were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form an electron transport layer of 250 A. Respectively. Lithium fluoride (LiF) 10 A thick was sequentially deposited on the electron transport layer and aluminum was deposited thereon to a thickness of 1000 A to form a cathode.

The deposition rate of the organic material was maintained at 0.4 to 0.7 A / sec, the lithium fluoride at the cathode was maintained at 0.3 A / sec, and the deposition rate of aluminum was maintained at 2 A / sec. - it was maintained at ⁷ ~ 5 10- ⁸ torr.

Examples 5 to 6

The organic light emitting devices of Examples 5 to 6 were fabricated in the same manner as in Example 4, except that the phosphorescent host material and the dimple content in the light emitting layer were changed as shown in Table 2 below. Comparative Examples 3 to 4

The organic light emitting devices of Comparative Examples 3 to 4 were fabricated in the same manner as in Example 4, except that the phosphorescent host material and the dimple content in the light emitting layer were changed as shown in Table 2 below. [Experimental Example 2]

The current, voltage, efficiency, color coordinates and lifetime of the organic light-emitting device fabricated in Examples 4 to 6 and Comparative Examples 3 to 4 were measured, and the results are shown in Table 2 below. At this time, T95 shows the initial luminance at a density of 20 mA / cm ²

100%, it means the time required for the luminance to be reduced to 95%.

[Table 2]

DESCRIPTION OF REFERENCE NUMERALS 1: substrate 2: anode

3: light emitting layer 4: cathode

5: Hole injection layer 6: Hole transport layer

7: light emitting layer 8: electron transporting layer

Claims

Claims:

[Claim 1]

A compound represented by the following formula (1) or (2):

In the above Formulas 1 and 2,

X is O or S,

Ri to R ₅ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d- ₆₀ alkyl; Substituted or unsubstituted d-60 haloalkyl; Substituted or unsubstituted d-60 alkoxy; Substituted or unsubstituted d-60 haloalkoxy; Substituted or unsubstituted C ₃ - ₆₀ cycloalkyl; Substituted or unsubstituted C ₂ - 60 alkenyl; Substituted or unsubstituted C ₆ -C ₆₀ aryl; Substituted or unsubstituted C ₆ -C ₆₀ aryloxy; Or substituted or unsubstituted C ₂ -C ₆₀ heteroaryl containing at least one heteroatom selected from the group consisting of N,

al to a5 are each independently an integer of 0 to 2;

[Claim 2]

The method according to claim 1,

And L < ₂ _> are each independently a single bond, or phenylene.

[Claim 3]

In Item 1,

Ar is any one selected from the group consisting of

In the above,

Y is O, S, or CZ ₄ Z ₅ ,

lx to < RTI ID = 0.0 > ₅ < / RTI > heavy hydrogen; halogen; Cyano; Nitro; Amino; Alkyl; d-20 haloalkyl; C ₆ - ₂₀ aryl; ₂₀ is a heteroaryl, - C ₂ containing zero or one or more heteroatoms of S

n1 to n3 each independently represent an integer of 0 to 3;

Claim 4

The method of claim 3,

[Claim 5] The method according to claim 1,

R < 1 > heavy hydrogen; halogen; Cyano; d- ₁₀ alkyl; Or C ₆ - ₂₀ aryl, compound.

[Claim 6]

The method according to claim 1,

Wherein said compound is represented by one of the following formulas 1-1 to 1-4 and 2-1 to 2-4:

[Chemical Formula 2-3] [Chemical Formula 2-4]

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

The definitions of X and Ar are as defined in Scheme 1 above.

[7]

The method according to claim 1,

Wherein said compound is any one selected from the group consisting of the following compounds:

Z.SZ.00 / 8T0ZaM / X3d Z.817C10 / 610Z OAV

Z.SZ.00 / 8T0ZaM / X3d Z.817C10 / 610Z OAV

8.

Gau electrode; A second electrode provided opposite to the first electrode; And at least one organic compound layer provided between the electrode and the second electrode, wherein at least one of the organic compound layers comprises a compound according to any one of claims 1 to 7. Organic light emitting device.