ORGANIC ELECTRIC ELEMENT USING COMPOUND FOR ORGANIC ELECTRIC ELEMENT, AND ELECTRONIC DEVICE THEREOF

Hereinafter, thereby, the cold air flows of the present invention embodiment drawing with an. rapidly and to reduce a memory reference to.

Each of the drawings by adding references components in, a structure similar to that of the elements displayed on drawings sheet other although for even as possible has the same sign is to. to significantly different. Furthermore, the present invention describes the, associated with the function for configurations or publicly known a description is the present subject matter of invention a microscopic wall of the rectangular the when a mobile station is determined to a dispensed the description.

The present constitution of the invention in to explain an element, number 1, number 2, A, B, (a), (b) a set of terms, such as that is capable of using optical. Such term components thereof a with other components for differentiating is, essentially component, corresponding to the terms or turn or sequence is not limited and the like. Is any component other components to "connected", "coupled" or "connection" the pixels include when, the components thereof other components connected directly to but can be connected or, each between components members another "connected", "coupled" or "connection" may be. to be understood that.

Furthermore, layer, film, region, wave other components of components of the cellular wireless communication example, exhibiting an "on" or "on" wall of the rectangular when, the other components "directly on the" as well as when another its intermediate components may also comprise a if there is a to be understood that.. Vice versa, the other portions on any configuration element "directly on the" wall of the rectangular when the people, Letters and the thing which another portion intermediate the is started it. to be understood.

The present specification and appends a the following is claimed as used in the, to dually function as a pipeline and not alternatively, a a, easy to equal meaning of terms:

Terms used in the present specification "halo" or "halogen" a fluorine free a description is other (F), bromine (Br), chlorine (Cl) or iodine (I) is.

Terms used in the present invention "alkyl" or "alkyl" a description is the other, the hand of the a free carbon 60 to 1 wherein the single water, straight chain alkyl group, branched chain alkyl group containing from, cycloalkyl (cycloaliphatic) to, alkyl-substituted alkyl cycloalkyl, cycloalkyl-substituted alkyl radical functional group saturated fat including..

Terms used in the present invention "alkene diary" or "alkyne diary" a without a description is the other, the hand of the each carbon number 2 to 60 has-, includes a capsule having at chain chain or linear, are not limited to.

"Cycloalkyl" used in the present invention terms a without a description is other carbon that has 60 to 3 the alkyl meaning, are not limited to.

Terms used in the present invention "alkoxy group", "alkoxy groups", or "alkyl jade time " alkyl with the oxygen radicals mixture by the addition of an initiator, a free other described with carbon 60 to 1, are not limited to.

Terms used in the present invention " biting jade group" or the oxygen radicals is attached " biting jade time " aryl initiator, a free other described with carbon 60 to 6, are not limited to.

Terms used in the present invention "aryl" and "5 arylene groups" a description is the other, the hand of the a free carbon with each 60 to 6, not limited to blood. In the present invention an aryl group or [...] single ring or multiple ring aromatics initiator, adjacent substituent is bind or react participate in includes aromatic ring formed. E.g., membered phenyl, ITO-glass substrate, flue [...] , [...] spiking, spiking may [...].

"Aryl" or "aralkyl" prefix meaning the. machine having radical substituted aryl group, and aryl group. For example R3 is substituted aryl group, and aryl group the biting alkyl it crawls , biting alkene diary is diary the alkene substituted aryl group, and aryl group, aryl group, and aryl group substituted radical the present specification has taught carbon water.

Furthermore, designated form are continuously prefix meaning first the order listed substituent is as ., meaning that the. For example, when will be biting and the cock time which it will know mixture by the addition of an initiator alkoxy groups substituted aryl group, and aryl group, a is replaced by the processing result alkoxy group when thread carbonyl alkoxy carbonyl group initiator, in addition when biting carbonyl alkene diarybiting carbonyl crossroad in the trench wherein mixture by the addition of an initiator diary the alkene substituted the biting carbonyl it crawls is carbonyl group to substituted aryl group, and aryl group.

Terms used in the present invention "hetero aryl" or "hetero 5 arylene groups" without a description is the other, the hand of the a, respectively, at least one carbon atoms including heteroatoms [...] initiator 2 to 60 aryl or, excitation are not limited to, single ring and multiple ring comprises at least one of, neighboring the beneficial device may be formed by associating an.

Terms used in the present invention "hetero ring " a description is the other, the hand of the a without includes one or more heteroatoms, carbon with 2 to 60, single ring and multiple ring comprises at least one of, of aliphatic cyclic hetero includes heteroaromatic ring and. Adjacent functional groups may be formed by associating an.

Terms used in the present specification "heteroatom" without a description is the other, the hand of the a N, O, S, exhibits and P or Si.

Other described a free, "aliphatic" terms used in the present invention carbon atoms 1 to 60 aliphatic hydrocarbon mixture by the addition of an initiator, the carbon atoms "of aliphatic cyclic" aliphatic hydrocarbons of 3 to 60. ring.

Other described a free, "ring" terms used in the present invention the carbon atoms of carbon number of aliphatic cyclic of 3 to 60 6 to 60 the aromatic ring of the ring or rings of carbon number of 2 to 60 ; and a fused ring combination of them a numeral key, includes saturated or unsaturated ring.

The aforementioned hetero compounds in addition to the other hetero compounds or radical includes one or more heteroatoms, are not limited to.

In addition a without a description is explicit, terms used in the present invention "a substituted or unsubstituted" "substituted" in the deuterium, to halogen, amino group, nitrile group, adamantanol can be, C₁-C₂₀ alkyl, C₁-C₂₀ alkoxide group, C₁-C₂₀ of halogenic acid-carboxylic acid, C₁-C₂₀ alkyl mote five pen , C₆-C₂₀mote five pen it will be biting of, C₂-C₂₀ alkenyl diary, C₂-C₂₀ of alkyne diary, C₃-C₂₀ of alkyl, C₆-C₂₀ aryl, deuterium is replaced by the processing result a C₆-C₂₀ aryl, C₈-C₂₀biting alkene of diary, silane, to boron, to germanium, and O, N, S, Si and P at least one selected from the group consisting of including heteroatoms C₂-C₂₀ring crossroad of selected from the group consisting of one or more 1 meaning is substituted with substituents, these substituents limited to not.

In addition a without a description is explicit, in the present invention used to operate close to the loop frequency formula for substituting to index of formula uses the definitions and to is.

Wherein, a is integer number of 0 is when substituent R¹ the absence wherein, when a user a is integer number of a is 1, R4 of R¹ a benzene the carbon one of carbon that bind to, 3 or 2 is a is integer number of which the coupled as follows in case R¹ are identical to each other can be the same or different, is integer number of a is 4 to 6 is the case in a manner similar to that bind to carbon benzene ring, the benzene while hydrogen bound to carbon in indication of the avoided.

According to one embodiment of the present invention Figure 1 shows a also organic device is exemplary.

With a 1 also, organic device according to one embodiment of the present invention (100) the substrate (110) formed on electrode number 1 (120), number 2 electrode (180) and number 1 electrode (110) and number 2 electrode (180) between the is provided with a organic layer including compound the present invention according to. The, number 1 electrode (120) and an anode (anode), number 2 electrode (180) which may be the cathode (cathode), when the number 1 number 2 the butt style which is[...] electrode may it will be a child node electrode.

ITO layers electrode number 1 (120) prints sequentially on hole injection layer (130), the hole transport layer (140), light emitting layer (150), the light takeout efficiency (160) and electronic injection layer (170) may include a. The, light emitting layer (150) to the first direction is formed on to connect an can be counted out. 2006, electronic stop layer, light emitting cadence layer (151), buffer layer (141) further may comprise an such as, the light takeout efficiency (160) obstruction layer hole and the like it may serve 2000.

Furthermore, it does but not shown, according to one embodiment of the present invention number 1 number 2 electrode and organic element during said organic compound layer of the first electrode opposite to a surface of at least one electrode on one surface of the, a film type passivation film is or optical efficiency enhancement layer may include further (Capping layer).

A is applied to the top ply of one embodiment aspect of the present invention said organic the compounds according hole injection layer (130), the hole transport layer (140), the light takeout efficiency (160), electronic injection layer (170), light emitting layer (150) of host or dopant or optical efficiency improved layer material can be used as 2000.

Organic electroluminescent device according to one embodiment of the present invention a variety of vapor deposition (deposition) manufactured by using a state-of is may be. Method evaporation such as CVD or PVD may be manufactured using, e.g., a metal film on the substrate and thermally conductive or metal oxide deposition or alloys thereof, and the anodes (120) is formed, hole injection layer thereon (130), the hole transport layer (140), light emitting layer (150), the light takeout efficiency (160) and electronic injection layer (170) formed organic layer including a, cathode thereon (180) it can be applied to by substrate and the second substrate can be produced.

Furthermore, ITO layers deposited using physical vapor deposition techniques a polymer material various non-method (solvent process) process or solvent method or a solution application method, e.g. spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, process permeablity, doctor blading process, screen printing process, such as thermal transfer or by method, and, thus, less number of layers of doped region is to be formed.. Method the present invention according to various ITO layers can be formed, method for forming the same of the present invention by the not rights range is limited.

According to one embodiment of the present invention materials used in the organic element which can emit light from the entire according to type, backlit or the double-emitting. may be.

Fairness easily and base station realize the high resolution has WOLED (White Organic Light Emitting Device) excellent while the, existing LCD using color filter of which can be manufactured contact point is turned off. Mainly backlight device, which is used as organic white light emitting element is to perform various structures are proposed and patent. Which are representative of a, R (Red), G (Green), juxtaposed to each other light emitting portions B (Blue) (side-by-side) manner, which, R, G, B (stacking) laminate in which a luminescent layer and manner, blue (B) organic in luminous layer an electro-luminescent and therefrom by means of the light beam using (photo-luminescence) self-luminous of inorganic phosphor (color conversion material, CCM) a color annular material is, such as, the present invention refers to such WOLED 2000 can also be applied to.

Furthermore, organic device according to one embodiment of the present invention an organic electroluminescent element, organic solar cells, organic photoconductor, organic transistor, monochromatic or white for illumination can be one.

Other embodiment of the present invention the above-mentioned relate organic electric device of the present invention and including display device, the display device including electronic device the control unit may comprise an. The, a current or future electronic device may be the server by wire or wireless communication terminal, for forming low K film using gaseous mobile communication terminal, PDA, electronic dictionary, PMP, remote, navigation, game machine, various TV, computer or includes electronic device.

Hereinafter, according to one aspect of the present invention relates to organic device.

In one in the embodiment of the present invention, the present invention refers to a derivative is represented by the following formula 1 to formula 4 including at least one of organic device with high.

The organic element electrode number 1 ; number 2 electrode; and said number 1 number 2 electrode and organic substances, layer positioned between the electrodes; the first to third locking States, said ITO layers to formula 1 a at least one derivative is represented by the following formula 4 may comprise an.

Said host and ITO layers including dopant can be includes a light emitting layer, said emitting layer to formula 1 a at least one derivative is represented by the following formula 4 may comprise an.

Said dopant light-emitting layer a fullerene derivative is denoted by chemical formula 1 a may include, said removed which is marked as a chemical formula 2 to at least one derivative is represented by the following formula 4 may comprise an.

On the other hand, said organic layer containing compounds are but may be only compound same type of sensor, the sensor, a disparate compound represented by formula 1 to formula 4 which is a mixture mixing 2 or more may be.

E.g., one embodiment of the present invention to the dopant material layer light 1-2 such as a individual compound 1-1 and 2 species may contain compounds of differing, 1-1 compound individual a, at least one 3 1-2 and 2-1, such as containing compounds of differing may be loaded with.

Furthermore, one embodiment of the present invention to operate close to the loop frequency host material layer light 3-2 such as a individual compound 3-1 and 2 of which may contain compounds of differing, 4-1 and 3-1 compound individual a of 2 such as a may contain compounds of differing, 3-1 compound individual a, 3-2 3-3 and 3, such as at least one compounds of differing which may contain, to individual compound 3-1, 4-1 5-1 and at least one 3, such as containing compounds of differing may be loaded with.

In other in the embodiment of the present invention, the present invention refers to said number 1 electrode the outer periphery and a negative pressure organic compound layer of the first electrode during one front surface side of said one or said number 2 electrode during one front surface side of said organic compound layer of the first electrode formed on at least one of the connector has one side with a first opposite an optical and parabola-layer including organic device with high.

Organic according to one aspect of the present invention are used a compound in which a. off at the first and the second.

< 화학식 1>< 화학식 1-1>< 화학식 1-2>

In said formula 1, the n integer of 0 to 4,

R¹ to R⁶, independently one of the other are, hydrogen; deuterium ; to halogen; cyano group; alkoxy carbonyl-, nitro-, ; C₆-C₆₀ aryl; O, N, S, Si and P at least one selected from the group consisting of including heteroatoms C₂-C₆₀ring of; C₁-C₅₀ alkyl; C₁-C₅₀ alkoxy group; C₂-C₂₀ diary alkenyl; and-L^a-N (R^a) (R^b); from the group consisting of can be selected. E.g., R¹ to R⁶, independently one of the other are, hydrogen, methyl, phenyl. combination of the conductor.

Furthermore, R¹ to R⁵ communicates with neighboring to least one annular combination intends to may form a, specifically R¹ and R², R² and a R³, R³ and R⁴ and/or R⁴ and a R⁵ at least one portions engaging each other and by forming rings can be. The ring acids which do not form R¹ to R⁵ the defined in can be identically defined.

R⁶ also neighboring intends to long and by forming rings at least one coupled can be. When n is integer larger than or equal to 2, plurality of R⁶ other adjacent and can be manufactured or different intends to part in combination and by forming rings from the remainder ring the acids which do not form said defined can be identically defined.

On the other hand, neighboring the are fused together, an annular long a C₃-C₆₀ of aliphatic cyclic of, C₆-C₆₀ the aromatic ring of the, O, N, S, Si and P at least one selected from the group consisting of including heteroatoms C₂-C₆₀ of heterocyclic, or combination of them which combination of the conductor; and a fused ring, single ring or multiple ring, may be saturated or unsaturated as well as can be ring.

Said L^a a single coupled; C₆-C₆₀ of 5 arylene groups; flue [...] ; C₃-C₆₀ aliphatic ring and the C₆-C₆₀ aromatic ring fusion ring ; and O, N, S, Si and P at least one selected from the group consisting of including heteroatoms C₂-C₆₀ring of; from the group consisting of can be selected.

Said R^a and R^b each independently a, C₆-C₆₀ aryl; fluorene diary; C₃-C₆₀ aliphatic ring and the C₆-C₆₀ aromatic ring fusion ring ; and O, N, S, Si and P at least one selected from the group consisting of including heteroatoms C₂-C₆₀ring of; from the group consisting of can be selected.

In said formula 1, the l integer of 0 to 2, the formula 1-1 or formula 1-2 A can be represented by.

In said formula 1-1, N the ring P (nitrogen) containing a substituted or unsubstituted C₂-C₂₀ring strangeness of, Q ring substituted or substituted C₆-C₂₀ may it will be an allyl of. The, the Ir N of ring P (nitrogen) (iridium) and coordination form a bisphenyl bond (carbon) C of ring Q (iridium) and the Ir can be forms a covalent bond.

Q ratio of crank shaft supporting said P when respectively is ring, i) the each permutation deuterium independently of each other; to halogen; C₆-C₂₀ aryl; fluorene diary; O, N, S, Si and P at least one selected from the group consisting of including heteroatoms C₂-C₂₀ring of; and C₁-C₂₀ alkyl; or selected from the group consisting of, ii) each substituent is a desired neighboring combination intends to long forming a least one annular, or iii) substituted ring P, Q ring substituents and by forming rings is provided to be easily assembled and can be.

In said formula 1-2, one 2 of said Ir O (oxygen) (iridium) and coordination form a bisphenyl bond, (iridium) and the other one of the nozzle and said Ir can be forms a covalent bond.

And, in said formula 1-2, R⁷ and R⁸, independently one of the other are, hydrogen; deuterium ; C₆-C₆₀ aryl; O, N, S, Si and P at least one selected from the group consisting of including heteroatoms C₂-C₆₀ring of; C₁-C₅₀ alkyl; C₁-C₅₀ alkoxy group; and C₂-C₂₀ diary alkenyl; from the group consisting of can be selected.

< 화학식 2>

In said formula 2, a and b each integer of 1 or 0, the a+b at least 1. The a and b respectively. a single joined when 0.

X and Y each independently a S, O, (R ') N, C (R') (R ") or Si (R ') (R") can be.

Said R ' and R " each independently a, hydrogen; C₆-C₆₀ aryl; O, N, S, Si and P at least one selected from the group consisting of including heteroatoms C₂-C₆₀ring of; C₁-C₅₀ alkyl; and C₂-C₆₀ diary alkenyl; from the group consisting of value can be selected, and by forming rings is provided to be easily assembled and can be.

Ar¹ the C₆-C₆₀ aryl; fluorene diary; O, N, S, Si and P at least one selected from the group consisting of including heteroatoms C₂-C₆₀ring of; C₁-C₅₀ alkyl; and-L^a-N (R^a) (R^b); from the group consisting of can be selected. The, L^a, R^a and R^b defined in each said weight, and is economical can be identically defined. E.g., Ar¹ is a phenyl, naphthyl, pyridine, pyrimidine, triazine, quinazoline, benzoimidazol. combination of the conductor.

L¹ a single coupled; C₆-C₆₀ 5 arylene groups of; O, N, S, Si and P at least one selected from the group consisting of including heteroatoms C₂-C₆₀ 5 arylene groups of; and 2 is aliphatic hydrocarbon group; from the group consisting of can be selected. E.g., L¹ a single coupled, phenyl, pyridine, pyrimidine, quinazoline. combination of the conductor.

The m being integers, of 0 to 2, each q and o is integer number of 0 to 4.

R⁹ to R¹¹, independently one of the other are, deuterium; C₆-C₆₀ aryl; O, N, S, Si and P at least one selected from the group consisting of including heteroatoms C₂-C₆₀ring of; C₁-C₅₀ alkyl; C₁-C₅₀ alkoxy group; C₂-C₂₀ diary alkenyl; and-L^a-N (R^a) (R^b); from the group consisting of can be selected. The, L^a, R^a and R^b defined in each said weight, and is economical can be identically defined. E.g., R⁹ to R¹¹, independently one of the other are, carbazole, dibenzofuran, indole. combination of the conductor.

Furthermore, R⁹ to R¹¹ intends to a black matrix at least one coupled to and by forming rings can be. The ring acids which do not form R⁹ to R¹¹ the defined in can be identically defined. E.g., when both m and a q 2, adjacent R⁹ engage each other the ring can be formed in the, R¹⁰ even the neighboring ring giga hetero an aryl group or independently of each other can be.

Well as, when integer larger than or equal to 2 is q, plurality of R⁹ each other and can be manufactured or different such, neighboring intends to some long from the remainder and by forming rings combination ring the acids which do not form said defined substituent can be selected from a group of.. O and/or m is integer larger than or equal to 2. is similarly treated are.

On the other hand, neighboring the are fused together, an annular long defined in said weight, and is economical can be identically defined.

< 화학식 3>

In said formula 3,

Z¹ to Z¹⁶, independently one of the other are C (R) or is N, Z⁵ to Z⁸ and at least one of the Z⁹ to Z¹² C (R) is at least one of, wherein Z⁵ to Z⁸ one and Z⁹ to Z¹² C C (R) of one of the R instead with said L². and may be engaged with a.

Furthermore, Z¹ to Z¹⁶ C (R) during adjacent when the first metal layer R and by forming rings combination intends to can be.

Hydrogen said R; deuterium ; to halogen; cyano group; alkoxy carbonyl-, nitro-, ; C₆-C₆₀ aryl; fluorene diary; O, N, S, Si and P at least one selected from the group consisting of including heteroatoms C₂-C₆₀ring of; C₁-C₅₀ alkyl; and -L^a-N (R^a) (R^b); from the group consisting of can be selected. The, L^a, R^a and R^b defined in each said weight, and is economical can be identically defined.

The W N (Ar³), S, O or C (R ') (R ") which may be, R' and R" defined in said each weight, and is economical can be identically defined.

Ar² and Ar³, independently one of the other are C₆-C₆₀ aryl; fluorene diary; O, N, S, Si and P at least one selected from the group consisting of including heteroatoms C₂-C₆₀ring of; C₁-C₅₀ alkyl; and C₆-C₆₀amine it will be biting of; from the group consisting of can be selected. E.g., Ar² and Ar³, independently one of the other are, phenyl, biphenyl, pyrazole, pyridine, pyrimidine, triazine, quinazoline. combination of the conductor.

L² each independently a single joined; C₆-C₆₀ 5 arylene groups of; O, N, S, Si and P at least one selected from the group consisting of including heteroatoms C₂-C₆₀ 5 arylene groups of; and 2 is aliphatic hydrocarbon group; from the group consisting of can be selected.

< 화학식 4>

In said formula 4,

R¹² to R²³, independently one of the other are hydrogen; deuterium ; to halogen; cyano group; alkoxy carbonyl-, nitro-, ; C₆-C₆₀ aryl; O, N, S, Si and P at least one selected from the group consisting of including heteroatoms C₂-C₆₀ring of; C₁-C₅₀ alkyl; C₁-C₅₀ alkoxy group; C₂-C₂₀ diary alkenyl; and-L^a-N (R^a) (R^b); from the group consisting of can be selected. The, L^a, R^a and R^b defined in each said weight, and is economical can be identically defined. E.g., R¹² to R²³, independently one of the other are, hydrogen, phenyl, dibenzothiophene. combination of the conductor.

Furthermore, R¹² to R²³ to a black matrix least one annular combination intends to may form a, specifically R¹² and a R¹³, R¹³ and R¹⁴, R¹⁴ and a R¹⁵, R¹⁵ and a R¹⁶, R¹⁶ and R¹⁷, R¹⁷ and R¹⁸, R¹⁸ and R¹⁹, R¹⁹ and a R²⁰, R²⁰ and R²¹, R²¹ and R²², R²² and a R²³ and/or R²³ and R¹² at least one to engage each other and by forming rings can be. The ring acids which do not form R¹² to R²³ the defined in can be identically defined. Long neighboring the are fused together, an annular weight, and is defined in said can be identically defined.

While, in said formula 1 to formula 4, said flue [...][...] spiking may include [...] spiking and diary.

Wherein, said aryl group, fluorene diary, hetero ring , fusion ring , aliphatic hydrocarbon group, alkyl, alkene diary, alkoxy group, deuterium [...] flue and 5 arylene groups each independently of each other; to halogen; silane ; parts by weight of a siloxane group; to boron; to germanium; cyano group; nitro ; C₁-C₂₀ alkyl be enveloped ; C₁-C₂₀ alkoxide group; C₁-C₂₀ alkyl; C₂-C₂₀ alkenyl diary; C₂-C₂₀ of alkyne diary; C₆-C₂₀aryl; deuterium is replaced by the processing result a C₆-C₂₀ aryl; fluorene diary; O, N, S, Si and P at least one selected from the group consisting of including heteroatoms C₂-C₂₀ring of; C₃-C₂₀ of alkyl; C 88800003078 88-C₂₀ of aralkyl; and C₈-C₂₀ of diary biting alkene ; a selected from the group consisting of are substituted with one or more substituents can be.

In another in the embodiment of the present invention, represented by said formula 1 compound can be display one formula.

< 화학식 5>< 화학식 6>

< 화학식 7>< 화학식 8>

< 화학식 9>< 화학식 10>

In formula 10 to said formula 5, R¹ to R⁸, l and n the formula 1 defined in can be identically defined.

In another in the embodiment of the present invention, represented by said formula 1 compound can be one compounds.

In another in the embodiment of the present invention, represented by said formula 2 compound can be one compounds.

In another in the embodiment of the present invention, the compounds represented by said formula 3 one compound can be.

In another in the embodiment of the present invention, represented by said formula 4 compound can be one compounds.

In another in the embodiment of the present invention, number 1 electrode; number 2 electrode; and said number 1 number 2 electrode and organic substances, layer positioned between the electrodes; a organic device including, said ITO layers including host and dopant which includes a light emitting layer, said light-emitting layer a dopant containing a fullerene derivative is denoted by chemical said formula 1, formula 4 to said formula 2 a removed said derivative is represented by the following at least one of display device including the organic electric device; and control unit for driving said display device; a provides including electronic device.

In hereinafter, of the present invention organic device contained in the synthetic derivative is represented by the following formula 1 to formula 4 organic in an electrical component and positive examples embodiment the manufacturing aspect of the present invention thereby, the cold air flows but specifically, example, embodiment of the present invention is not limited to exemplify.

Synthetic e.g.

Said method performed such as compound restrains the limited to not.

I. Formula 1 synthesis ofe.g.

Illustratively derivative is represented by the following the present invention according to formula 1 (Product) known as a raw material of the reaction of 1 or 2 as a raw material of the azo produced by the path of but not limited to.

< 반응식 1>L when 0 is

< 반응식 2>L is 1 or 2 when

1. Sub e.g. synthesis of 1

Sub 1 1 of said known as a raw material of the reaction of 3 known as a raw material of the produced by the path of but not limited to.

< 반응식 3>

4-bromo-2-chloro-5-methylpyridine (1 equivalent) of THF (1mmol/starter 4.4 ml) to senses a rotation velocity of the disk to, Sub 1 (2) (1 equivalent), Pd (PPh₃)₄ (0.05 equivalent), K₂ CO₃ (3 equivalent), water (2.2 ml/starter 1mmol) after is added is, 80 °C stirring section. When reaction is completed CH₂ Cl₂ and a water extraction of organic layer after MgSO₄ to dry a silica gel column with a compound formed after separating the products Sub 1 (3) is obtained. Again the first and second method Sub 1 (3) in (1 equivalent) of THF (1mmol/starter 4.4 ml) to senses a rotation velocity of the disk to, Sub 1 (4) (1.1 equivalent), Pd (PPh₃)₄ (0.05 equivalent), water (2.2 ml/starter 1mmol) after is added is, 80 °C stirring section. When reaction is completed CH₂ Cl₂ and a water extraction of organic layer after MgSO₄ to dry a silica gel column with a compound formed after separating the products Sub 1 is obtained.

While, then, a exemplary Sub 1 the LR is are not limited to, their FD-MS as 1-table a value.

[Table 1-1]

2. Product e.g. synthesis of 1

Sub 1 (4 equivalent) to Ir (acac)₃ (1 equivalent) doesn't have any error frames, Glycerol 18-24 under nitrogen with the reflux time. Reaction is terminated materials solid which is obtained after the purified by column chromatography in the vacuum pump the 5 drying time of the last compound is obtained.

(1) compound 1-4 synthesise.g.

Sub 1-4 (10.37g, 40mmol) to Ir (acac)₃ (4.89g, 10mmol) Glycerol 350 ml under nitrogen together with doesn't have any error frames, the reflux time 18. Reaction is terminated materials solid which is obtained after the purified by column chromatography in the vacuum pump the drying time a 5 6.12g 1-4 the compounds obtained (yield: 63%).

(2) compound 1-20 synthesise.g.

Sub 1-20 (13.4g, 40mmol) to Ir (acac)₃ (4.89g, 10mmol) Glycerol 350 ml doesn't have any error frames, 24 under nitrogen together with the reflux time. Reaction is terminated materials solid which is obtained after the purified by column chromatography in the vacuum pump the 5 drying time for 1-20 7.25g the compounds obtained (yield: 58%).

While, according to synthetic such as said compounds that are produced are enabled to operate close to the loop table FD-MS of 1-25 to 1-1 1-2 and a equal value.

[Table 1-2]

3. Product e.g. synthesis of 2

2 of said known as a raw material of the reaction of 4 Product 2 detects a known as a raw material of the produced by the path of but not limited to.

< 반응식 4>

(1) compound 2-26 synthesise.g.

Ir compound (10.0g, 7mmol) to pentane-2, 4-dione (7g, 70mmol), Na₂ CO₃ (7.4g, 70mmol), 2-ethoxy ethanol 100 ml in 130 °C under nitrogen for inserting and removing reacted time 24. Reaction is terminated materials solid which is obtained after the purified by column chromatography in the vacuum pump the drying time 3 2-26 1.6g of the compounds obtained (yield: 30%).

4. Product e.g. synthesis of 3

Product 3 of said 2 known as a raw material of the 5 known as a raw material of the reaction of 6 as a raw material of the azo or produced by the path of but not limited to.

< 반응식 5>

< 반응식 6>

(1) synthetic e.g. Sub A

2-phenylpyridine (2.5 equivalent) to IrCl₃ (1 equivalent) doesn't have any error frames, 2-ethoxy ethanol: H₂ O 3:1 ratio of the paste has better mouth feeling and solution on 140 °C reacted time 24 in under nitrogen. When reaction is completed the solids that obtained CH₂ Cl₂ and a water extraction of organic layer after MgSO₄ to dry silica gel and BTS having no color and combined about 2 cm. by passing through at least one filter thickness. Recrystallization is reduced to settle the unbalance concentrating filtered liquid in the vacuum pump if there is the specific 5 a obtained Sub A the products drying time.

(2) synthetic e.g. Sub B

Sub A (1 equivalent) and a (about 10 equivalent) a Sub A-a Na₂ CO₃ (10 equivalent) in 130 °C 2-ethoxy ethanol with paste has better mouth feeling and reacted time 24. Reaction is terminated filtering the solid material which is obtained behind the column chromatography in the vacuum pump the purified by 3 obtained a Sub B the products drying time.

(3) compound 2-1 synthesise.g.

Sub A to 2-ethoxy ethanol (10.7g, 10mmol), Sub 1-1 (6.47g, 25mmol), Silver triflate (2.5g, 10mmol) in 130 °C under nitrogen for inserting and removing reacted time 24. Reaction is terminated materials solid which is obtained after the purified by column chromatography in the vacuum pump the drying time for the compounds 3 2-1 3.1g obtained (yield: 36%).

(4) compound 2-15 synthesise.g.

Sub A to 2-ethoxy ethanol (10.7g, 10mmol), Sub 1-15 (7.15g 25mmol), Silver triflate (2.5g, 10mmol) in 130 °C under nitrogen for inserting and removing reacted time 24. Reaction is terminated which is obtained after the solid materials the purified by column chromatography in the vacuum pump 3 a drying time 3.0g 2-15 the compounds obtained (yield: 38%).

(5) compound 2-19 synthesise.g.

Furthermore, the frame is made up Ir Sub B (5.99g, 10mmol) to Sub 1-19 in Ancillary ligand (5.0g, 15mmol) for inserting and removing 20 minutes at a temperature of 240 °C Glycerol with 120W microwave by him. Reaction is terminated which is obtained after the solid materials the purified by column chromatography in the vacuum pump 3 a drying time 2.8g 2-19 the compounds obtained (yield: 33%).

(6) compound 2-22 synthesise.g.

Furthermore, the frame is made up Ir Sub B (5.99g, 10mmol) to Sub 1-22 in Ancillary ligand (5.0g, 15mmol) for inserting and removing 20 minutes at a temperature of 240 °C Glycerol with 120W microwave by him. Reaction is terminated which is obtained after the solid materials the purified by column chromatography in the vacuum pump 3 a drying time 2.7g 2-22 the compounds obtained (yield: 32%).

While, according to synthetic such as said compounds that are produced are enabled to operate close to the loop value FD-MS of 2-25 to 2-1 as 1-3 table.

[Table 1-3]

II. Formula 2 synthesis ofe.g.

Illustratively 3-9 compounds in (Product) derivative is represented by the following the present invention according to formula 2 synthesis of 7 known as a raw material of the relate reaction of produced by the path of but not limited to.

< 반응식 7>

(1) synthetic e.g. Sub 3-2

Sub 3-1 (5.3g, 20mmol) anhydrous Ether is dibutyl phthalate or dimethyl, and one to lower temperature of the water within a reaction -78 ° C, n-BuLi (2.5M in hexane) (1.4g, 22mmol) is slowly after a and blended, reactants visitor is checked through a stirring 30 minutes. Then back to the reactor and one to lower temperature of the water within a -78 ° C Triisopropyl borate (5.6g, 30mmol) a blended section. At room temperature and water are behind obtain a lead line having a dilution 2N HCl the. extended storage and is easily carried. When reaction is completed ethyl acetate and a water extraction of organic layer after MgSO₄ to dry a are formed after the Sub 3-2 3.2g a silicagel column and floor product obtained (yield: 71%).

(2) synthetic e.g. Sub 3-3

Sub 3-2 (3.2g, 14.2mmol) and a 1-iodo-2-nitrobenzene (3.5g, 14.2mmol), Pd (PPh₃)₄ (0.5g, 0.4mmol), K₂ CO₃ (5.9g, 42.6mmol) anhydrous THF and a using the oxide layer as a layer covering the both to small amounts of water, the reflux time 24. Reaction temperature of the water within a process upon end and marked on the specific a high temperature to the normal temperature, CH₂ Cl₂ extraction of wipe its into water. Small amounts of water anhydrous MgSO₄ after filtration and decompresses for the removal of, organic solvent is concentrated and generated by products which are implicated in the separating column for Sub 3-3 2.9g obtained (yield: 68%).

(3) synthetic e.g. Sub 3-4

Sub 3-3 (2.9g, 9.6mmol) and triphenylphosphine (7.5g, 28.8mmol) for o-dichlorobenzene is dibutyl phthalate or dimethyl, recirculating a stirring time was 24. Of methanol surface reaction being terminated after removing the solvent using, a concentrated product 1.7g Sub 3-4 the separating column a (yield: 65%)obtained.

(4) compound 3-9 synthesise.g.

Sub 3-4 (1.7g, 6.2mmol) and a Sub 3-5 (1.9g, 6.2mmol) paste has better mouth feeling and toluene a Pd₂ (dba)₃ (0.3g, 0.31mmol), PPh₃ (0.2g, 0.62mmol), NaO t-Bu (1.8g, 18.6mmol) behind each added, in 100 °C. recirculating a stirring time 24. Ether and a water extraction of organic layer after MgSO₄ to dry a formed after silicagel column are the compounds and recrystallization 2.0g a 3-9 obtained (yield: 63%).

While, according to said synthetic such as 3-32 to 3-1 and the compounds that are produced are enabled to operate close to the loop value FD-MS of table 2 and a equal.

[Table 2]

III. Formula 3 synthesis ofe.g.

The present invention according to formula 3 illustratively 4-1 compounds in (Product) compounds represented by general synthesis of 8 known as a raw material of the relate reaction of produced by the path of but not limited to.

< 반응식 8>

3-bromo-9-phenyl-9H-carbazole (6.4g, 20mmol) senses a rotation velocity of the disk to a THF to, (9-(4, 6-diphenyl-1, 3, 5-triazin-2-yl)-9H-carbazol-3-yl) boronic acid (8.8g, 20mmol), Pd₂ (dba)₃ (0.9g, 1mmol), PPh₃ (0.5g, 2mmol), NaO t-Bu (5.8g, 60mmol), toluene (210 ml), after water, added thereto, . recirculating a stirring. When reaction is completed after ether and a water extraction of organic layer MgSO₄ to dry a are formed after silicagel column and recrystallization 9.2g 4-1 of the compounds obtained (yield: 72%)

While, according to said synthetic such as 4-24 to 4-1 and the compounds that are produced are enabled to operate close to the loop value FD-MS of as 3 table.

[Table 3]

IV. Formula 4 synthesis ofe.g.

Illustratively 5-6 compounds in (Product) derivative is represented by the following the present invention according to formula 4 synthesis of 9 known as a raw material of the relate reaction of produced by the path of but not limited to.

< 반응식 9>

Triphenylen-2-ylboronic acid (5.4g, 20mmol) senses a rotation velocity of the disk to a THF to 2-(4-bromophenyl)-4, 6-diphenyl-1, 3, 5-triazine (7.8g, 20mmol), Pd₂ (dba)₃ (0.9g, 1mmol), PPh₃ (0.5g, 2mmol), NaO t-Bu (5.8g, 60mmol), toluene (210 ml) after is added is, . recirculating a stirring. When reaction is completed after ether and a water extraction of organic layer MgSO₄ to dry a are formed after silicagel column and recrystallization 5-6 7.5g of the compounds obtained (yield: 70%).

While, according to said synthetic such as 5-12 to 5-1 and the compounds that are produced are enabled to operate close to the loop value FD-MS of table 4 and a equal.

[Table 4]

Organic in an electrical component manufacturing evaluation

[In the embodiment1] green organic electroluminescence device (phosphorescent dopant)

According to one embodiment of the present invention a compound used as transparent dopant material according to conventional method was produced organic electroluminescent device. First, the form of a (anode) on ITO layer N¹-(naphthalen-2-yl)-N⁴, N⁴-bis (4-(naphthalen-2-yl (phenyl) amino) phenyl)-N¹-phenylbenzene-1, 4-diamine (hereinafter to the "2-TNATA" hereinafter) the vacuum deposition of film thickness of 60 nm was hole implantation layer. Furthermore, on said hole injection layer 4, 4-bis [N- (1-naphthyl)-N-phenylamino] biphenyl (hereinafter the "NPD" to hereinafter) of 60 nm thickness is formed to allow the plating solution hole transporting layers the vacuum deposition. And, the hole transport layer on said with 3-9 compound of the present invention, a dopant from the 1-1 compound of the present invention at a weight ratio 95:5 by doping 30 nm thickness is formed to allow the plating solution the application status of the vacuum deposition. Next, on said light emitting layer (1, 1'-bis phenyl)-4-oleate is lengthwisely) bis (2-methyl-8-quinoline [...]) aluminum (hereinafter the "BAlq" to hereinafter) of the vacuum deposition thickness 10 nm and stop hole, said 2006 on tris (8-quinolinol) aluminum (hereinafter "Alq₃" to the hereinafter) of 40 nm thickness is formed to allow the plating solution vacuum evaporation woman electronic transporting layers. After, said alkali metal [...] halo on the light takeout efficiency 0.2 nm for a LiF electronic a plasma and implantation layer, then a plasma of 150 nm for Al comprising a negative electrode by forming a been produced with at organic electroluminescent device.

[In the embodiment2] to [in the embodiment51] green organic electroluminescence device (phosphorescent dopant)

Light-emitting layer dopant material 5 table reserving 1-1 compound of the present invention is and 2-1 to 2-26 1-25 to 1-2 compound of the present invention using one of the in the embodiment 1 except the same method been produced with at organic electroluminescent device.

[Compared e.g. 1]

Light-emitting layer dopant material 1 compound compared reserving 1-1 compound of the present invention using the in the embodiment 1 except the same method been produced with at organic electroluminescent device.

< comparative chemical compound 1> Ir (ppy)₃

1 of the present invention in the embodiment 1 to in the embodiment 51 and comparison e.g. organic electroluminescent device produced by forward biased to research of the photoresist by applying direct current electroluminescent PR-650 yarn (photoresearch) corresponding advertisement based on the shown measuring characteristics (EL), organic light emitting layer made in in 5000cd/m2 [...] T95 through the equipment for measuring life time of it was determined that life. 5 table which is marked as a chemical determination and a equal.

[Table 5]

The technician knows from said table 5 understructure can be result of, material for organic electroluminescence device of the present invention organic electroluminescent device using a formula 2 a fullerene derivative is denoted by chemical formula 1 and removed from a fullerene derivative is denoted by chemical relationship with the derma when applied with a dopant displaying green light-emitting layer is, in 1 compound compared Ir (ppy)₃ that emit light at a given time using with a dopant layer on upper and lower glass and resulting in a lower the driving voltage, a the water efficiency and service life it has been confirmed.

A comparison is than combination of and a host dopant compounds of the present invention host, the dopant, combination has a much better energy balance (Energy balance), the present invention, and the packing density of the compound (packing density) is the better the resulting in the drive voltage of the element is lower, and the, , and provides a significant increase in efficiency and service life is determined to be.

[52 in the embodiment] green organic electroluminescence device (phosphorescent dopantmixture host)

According to one embodiment of the present invention a compound used as transparent dopant material according to conventional method was produced organic electroluminescent device. First, the form of a ITO layer (anode) 2-TNATA on the vacuum deposition of film thickness of 60 nm was hole implantation layer. Furthermore, a 60 nm thickness NPD said hole injection layer on the hole transporting layers the front/rear sides of the vacuum deposition. And, the hole transport layer on said mixing 5-4 and a 3-9 compound of the present invention the host material, 95:5 from the dopant for 1-1 compound of the present invention at a weight ratio by doping 30 nm thickness is formed to allow the plating solution the application status of the vacuum deposition. Next, a 10 nm emitting layer on said BAlq hole the vacuum deposition thickness and stop, 2006 on said Alq₃ electronic evaporation woman vacuum thickness of 40 nm is formed to allow the plating solution transporting layers. After, said alkali metal [...] halo on the light takeout efficiency 0.2 nm for a LiF electronic a plasma and implantation layer, then a plasma of 150 nm for Al comprising a negative electrode by forming a been produced with at organic electroluminescent device.

[53 in the embodiment] to [in the embodiment72] green organic electroluminescence device (phosphorescent dopantmixture host)

Light-emitting layer dopant material 1-1 compound of the present invention is 6 table reserving 1-21 to 1-2 compound of the present invention using one of the in the embodiment 52 except the same method been produced with at organic electroluminescent device.

[73 in the embodiment] to [in the embodiment100] green organic electroluminescence device (phosphorescent dopantmixture host)

Removed material 5-4 and a 3-9 compound of the present invention instead 4-1 and a 3-9 compound and an electrolytic solution for a, light-emitting layer dopant material 6 table reserving 1-1 compound of the present invention is and 2-1 to 2-24 1-25 to 1-21 compound of the present invention using one of the in the embodiment 52 except the same method been produced with at organic electroluminescent device.

[[ 102 in the embodiment ] in the embodiment 101 and green organic electroluminescence device (phosphorescent dopantmixture host)

Removed material 4-1 compound instead 5-4 and a 3-9 compound of the present invention and and the 5-4, light-emitting layer dopant material 1-1 compound of the present invention is 6 table reserving 2-26 or 2-25 compound of the present invention using the in the embodiment 52 except the same method been produced with at organic electroluminescent device.

In the embodiment 102 to of the present invention in the embodiment 52 organic electroluminescent device produced by forward biased to research of the photoresist by applying direct current electroluminescent PR-650 yarn (photoresearch) corresponding advertisement based on the shown measuring characteristics (EL), organic light emitting layer made in in 5000cd/m2 [...] T95 through the equipment for measuring life time of it was determined that life. 6 table which is marked as a chemical determination as.

[Table 6]

The technician knows from said table 6 result of understructure can be, material for organic electroluminescence device of the present invention organic electroluminescent device using a single hosts on upper and lower glass mixture host of using a when green is used in a light emitting layer the efficiency and in an improved service life of the sliding member is can be viewed. Due to the mixed connection from the first or second host when the host single bandgap than and including an emitting layer is widened in charge balance (charge balance) is the thermal conductivity efficiency and increased life is it is judged that the.

[103 in the embodiment] (phosphorescent dopant)yellow organic electroluminescence device

According to one embodiment of the present invention a compound used as transparent dopant material according to conventional method was produced organic electroluminescent device. First, the form of a ITO layer (anode) 2-TNATA on the vacuum deposition of film thickness of 60 nm was hole implantation layer. Furthermore, a 60 nm thickness NPD said hole injection layer on the hole transporting layers the front/rear sides of the vacuum deposition. And, the hole transport layer on said 4-1 the host material of the present invention compound, 95:5 from the dopant for 1-1 compound of the present invention at a weight ratio by doping 30 nm thickness is formed to allow the plating solution the application status of the vacuum deposition. Next, a 10 nm emitting layer on said BAlq hole the vacuum deposition thickness and stop, 2006 on said Alq₃ electronic evaporation woman vacuum thickness of 40 nm is formed to allow the plating solution transporting layers. After, said alkali metal [...] halo on the light takeout efficiency 0.2 nm for a LiF electronic a plasma and implantation layer, then a plasma of 150 nm for Al comprising a negative electrode by forming a been produced with at organic electroluminescent device.

[In the embodiment104] to [122 in the embodiment] (phosphorescent dopant)yellow organic electroluminescence device

Light-emitting layer dopant material 7 table reserving 1-1 compound of the present invention is and 2-1 to 2-10 1-10 to 1-2 compound of the present invention using one of the in the embodiment 103 except the same method been produced with at organic electroluminescent device.

[Compared e.g. 2]

Light-emitting layer dopant material 2 compound compared reserving 1-1 compound of the present invention using the same said in the embodiment 103 except method been produced with at organic electroluminescent device.

< 비교화합물 2>PO01

2 of the present invention in the embodiment 103 to in the embodiment 122 and comparison e.g. organic electroluminescent device produced by forward biased to research of the photoresist by applying direct current electroluminescent PR-650 yarn (photoresearch) corresponding advertisement based on the shown measuring characteristics (EL), organic light emitting layer made in in 5000cd/m2 [...] T95 through the equipment for measuring life time of it was determined that life. 7 table which is marked as a chemical determination as.

[Table 7]

The technician knows from result of said table 7 collected and can be, material for organic electroluminescence device of the present invention organic electroluminescent device using a formula 3 emitting compounds represented by general formula 1 and removed from a fullerene derivative is denoted by chemical relationship with the derma when applied with a dopant displaying an yellow light-emitting layer is, PO01 in 2 compound compared using with a dopant layer that emit light at a given time on upper and lower glass and resulting in a lower the driving voltage, and to improve the efficiency and service life it has been confirmed.

the table 5 as well 51 to in the embodiment 1 of the comparison of the combination of and a host dopant compound combination, the dopant, host of the present invention than much better the energy balance has, the better the is, and the packing density of the compound the present invention resulting in the drive voltage of the element is lower, and the, , and provides a significant increase in efficiency and service life is determined to be.

Or more description describes illustratively of the present invention to to a modem, the present invention is in the field of the typically encountered in having knowledge of an essential element of the present invention grow or not the current source from deviating from variety of changeable will. Therefore, the present specification to a disclosure and to limit the present invention are in the embodiment is supported by the upper case and for described, such embodiment of the present invention and/or at least two different range event not limited. If of the present invention scope of protection which must be interpreted by, in the range equivalent and all connections to the technique including range rights of the present invention should be interpreted to will.