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

Hereinafter, with reference to the attached drawing of the present invention in the embodiment detailed as follows.

Each of the drawings in adding references components, although other drawing even for the same components displayed on a possible code accomplishing the same may have a significantly negative. In addition, the present invention is connected to the described, publicly known or a function of the associated specific description the subject matter of invention description if a haze can be decided to be dispensed to each other.

The constitution of the invention described is provided to element, number 1, number 2, A, B, (a), (b) using terms such as can be. Other components such terms having an element discriminate between the hell of, its terms corresponding components are not limited by the nature of the or the like or sequence. Any component and other components "connected", "coupled" or "connected" are blocked when described, other components or the components thereof are connected directly but can be connected, each between components of the other components "connected", "coupled" or "connected" is a device that may be will be.

In addition, layer, film, region, a component of "on" or "on" other components such as plate changed when, as well as any other components when "directly on" another intermediate components may also include a will be that it will be used. On the contrary, if any component other portions intermediate "directly on" another motor vehicle is started without understanding that it will be.

The following is claimed as used in the specification and appended, not otherwise mentioned, for the meanings of terms to such as disclosed.

"Halo" or "halogen" is other descriptive terms used in the specification free fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) are disclosed.

The present invention "alkyl" or "alkyl group" of other terms used in the description is free carbon number 1 to 60 has a single bond, linear alkyl, branched alkyl group, a cycloalkyl (alicyclic), alkyl - substituted cycloalkyl, cycloalkyl - substituted alkyl saturated aliphatic radical of the bondable functionality including big.

The present invention "halo alkyl" or "halogen alkyl" of other terms used in the description are substituted with alkyl halogen-free big.

The present invention "alkene diary" or "alkynyl group" of other terms used in the description is in each carbon number 2 to 60 free process for preparing has, such as caprylic or side chain chain that comprises a, one number herein are not disclosed.

"Cycloalkyl" is other descriptive terms used in the present invention to free a 3 to 60 and has an alkyl carbon a number means, number herein are not disclosed.

The terms used in the present invention "alkoxy group", "alkoxy", or "alkyl jade time" means oxygen radicals and fluoroalkyl group is attached, has a carbon number of 1 to 60 other descriptive free, one number herein are not disclosed.

The present invention is oxygen radicals attached to terms used in "biting jade group" or "[...]" means aryl which, has a carbon number of 6 to 60 other descriptive free, one number herein are not disclosed.

The present invention "fluorene diary" or "flue [...]" of other terms used in the description in R is lower than each have battery, R 'and R "is 1 or 2 and the both are H means is functional groups," substituted fluorene "includes a substituent R, R', R" group "or" substituted the flue [...] substituted and due at least one meaning other than hydrogen, R and R ' engage one another when they are carbon with cyber comprising compound formed.

The present invention "aryl" and "it will be biting, [leyn" of other terms used in the description is lower than 6 to 60 each having carbon number, the one number are not disclosed. In the present invention it will be biting and [leyn it crawls aryl group or single annular, ring assembly, bonded various ring-based, cyber compounds etc..

The present invention includes "heteroaryl group" or "hetero [...]" used terms such as "hetero it will be biting, [leyn" as well as non-aromatic ring which may contain an aromatic ring, each including one or more heteroatoms atoms to carbon atoms is lower than other descriptive 2 means the number herein one loop of 60 or not the. The term "heteroatom" used in the specification description of other free N, O, S, P or Si exhibit, hetero ring heteroatoms including single annular, ring assembly, bonded various ring-based, cyber justice e applies to compounds and the like.

In addition "hetero [...]" is, instead SO carbon has an₂ The system also includes a ring including can be. For example, "hetero [...]" receive a next compound substrate.

In the present invention which comprises a unitary ring and multi annularity terms used in "ring", as well as hydrocarbon ring including at least one hetero atoms and heterocyclic, aromatic and nonaromatic ring substrate.

In the present invention terms used in "polycyclic" is biphenyl, such as separating ring assembly (ring assemblies), bonded (fused) ring systems and cyber which various compounds, aromatic as well as non-aromatic may contain, as well as heterocyclic hydrocarbon ring including at least one hetero atoms it contains.

In the present invention terms used in "ring assembly (ring assemblies)" includes two or more ring-based (single ring or bonded ring-based) single bond or double bond directly connected to each other via such ring located in a ring-based total number of directly connecting between a compound characterized by a big number 1 the dog. The same or a different ring system is single bond or double bond ring aggregates can be interconnected directly via.

In the present invention includes at least two terms used in "bonded various ring-based" sharing of atoms of the annular joint (fused) and which means, two or more of hydrocarbon ring system is junction forms thereof and at least one hetero atoms including at least one hetero ring taking count of crosses etc. bonded form. These bonding of a number of ring-based aromatic ring, a heteroaromatic ring, a combination of aliphatic or ring can be.

Terms used in "cyber compounds" in the present invention is' cyber (spiro union) connected ' has, the annulus is only 1 share of atoms of 2 connected cyber achieved by big connection. The, two ring the shared atoms' cyber to atoms' and as, according to a number of atoms so as to located in a cyber compounds to each 'mono cyber to -', 'dice to fine -', 'to tris fine -' compound this may be.

In addition, when a designated prefix meaning substituents listed in a continuous first order means that the substrate. For example, when will be biting and the cock time which it will know which means with allyl substituted alkoxy, alkoxy substituted with alkoxy carbonyl group which when [...] means, wherein the biting carbonyl it crawls in addition when biting carbonyl crossroad substituted alkenes which means a carbonyl substituted with allyl biting carbonyl alkene diary diary residue.

In addition, without explicit description that, in the present invention in the terms used in "a substituted or unsubstituted" "substituted" deuterium, halogen, amino, nitrile, nitro, C₁ - C₂₀ Alkyl, C₁ - C₂₀ Alkoxy group, C₁ - C₂₀ Alkyl hydroxybutyrolactone, C₁ - C₂₀ Alkyl [...], C₆ - C₂₀ Of mote five pen it will be biting, C₂ - C₂₀ An alkenoic diary, C₂ - C₂₀ Of alkyne diary, C₃ - C₂₀ Of cyclo-alkyl, C₆ - C₂₀ Aryl, substituted with deuterium C₆ - C₂₀ Aryl, C₈ - C₂₀ Of biting alkene diary, silane, for boron, germanium to, fluorene diary, and O, N, S, Si and P including C hetero atoms selected from the group consisting of at least one₂ - C₂₀ Heteroatoms selected from the group consisting of at least one substituted 1 ring crossroad which means, these process is provided one number are not endured.

The specification of each symbol and substituted aryl group exemplified in example, it will be biting, [leyn, such as hetero [...] corresponding to 'name' is' to reflect hydrolysis of name 'section described, ' parent compound name ' disapproval form of the substrate. For example, in the case of electromagnetic wave is [...] 'phenanthrene', 'a' is 1 is of '(a) [...]' is for 2 to the 'lung difficulty [thu reel [leyn (a)' section name of hydrolysis such as charge described, regardless of the form of the substrate hydrolysis parent compound name 'phenanthrene' disapproval. Similarly, even if pyrimidine, regardless of 'pyrimidine' hydrolysis described or, if the pyrimidine anomers 1 (a), 2 (a) in the case of hydrolysis of corresponding pyrimidine [...] is such as' name of ' disapproval form of the substrate.

In addition, without explicit description that, in the present invention represented by formula formula index of definitions used by substituent definitions and equal to the received signals.

Wherein, a is an integer of 0 when R substituents¹ In the absence which meaning, i.e. a benzene is 0 when combined with all of the dispersing medium has an carbon, the carbon bonded hydrogen or compounds of formula can be protruded. In addition, a is an integer from 1 whether substituent R¹ Forming one of the benzene ring carbon which will bind to the carbon, for example when a is 2 or 3 can be coupled together under an integer, integer is 4 to 6 and in a similar manner even when a carbon which will bind to the benzene ring, R when a is 2 or more levels¹ Or each other's personal persona disclosed.

In the embodiment according to one example of the present invention Figure 1 shows a organic electroluminescence element also are disclosed.

The reference also 1, one in the embodiment according to of the present invention organic electrical component (100) substrate (110) formed on electrode number 1 (120), number 2 electrode (180) and number 1 electrode (120) and number 2 electrode (180) between the present invention according to a solvent including compounds with each other. The, number 1 electrode (120) and the cathode (positive electrode), number 2 electrode (180) and can have a cathode (cathode), the butt style which is number 1 number 2 electrode be [...] electrode if it will be a child node.

Organic compound layer is formed electrode number 1 (120) sequentially on hole injection layer (130), hole (140), a light emitting layer (150), alkali metal-containing fullerene (160) and with an (170) can be comprising. The, exposed to at least one of these layers, hole obstruction layer, electronic obstruction layer, light emitting [...] (151), electronic [...], buffer layer (141) may further include, alkali metal-containing fullerene (160) electrons are serves like peeling may be, hole (140) and alkali metal-containing fullerene (160) is 1 can be formed inside the cathode.

In addition, it does but not shown, in the embodiment according to number 1 and number 2 of the present invention one surface of at least one organic layer of said organic an electrical element can electrode formed on one surface opposite further includes a protective layer or optical efficiency enhancement layers (Capping layer) can be.

Said organic layer applied in the embodiment according to one of the present invention compounds are hole injection layer (130), hole (140), light emitting [...] (151), electronic [...], alkali metal-containing fullerene (160), with an (170), light emitting layer (150) made up of a host or doping or efficiency improvement can be used it will rain. For example, the light emitting layer of the present invention compound (150), hole (140) and/or a light emitting [...] (151) may be using the same are disclosed.

On the other hand, even the same core which is a methyl substituent coupling along band gap (band gap), electrical characteristics, interface characteristics may change is, for selecting and coupled subsystems are coupled to core (sub)- forward and for each combination of substituents, in particular energy level between T and each organic layer₁ Value, such as the inherent properties of material (mobility, interface characteristics) when a long life and a high efficiency when an optimal combination can be.

As already described, generally organic electroluminescent element hole in order to solve with [song layer number is a luminous door hole forming light-emitting layer is preferably a light emitting cadence layer, each light emitting layer (R, G, B) according to different light emitting [...] development time switch are disclosed. On the other hand, when light emitting [...] hole and a light emitting layer (host) with the kernel of the correlation similar core used in an organic layer if used different features as described in the literature to a control of a doctorate.

Thus, in the present invention formula 1 compound having a hole and/or a light emitting organic layer formed using cadence layer between each energy level and T₁ Value, the inherent properties of material such as organic electroluminescence (mobility, interface characteristics) can be simultaneously improving of prolonging the life and efficiency is optimized.

The organic electroluminescent device in the embodiment according to one of the present invention various deposition (deposition) number in an bath using are disclosed. PVD or CVD method can be provided on the tank which number using, for example, depositing a metal film on the substrate or conductive metal oxides or alloys thereof anodes (120) is formed, on the hole injection layer (130), hole (140), a light emitting layer (150), alkali metal-containing fullerene (160) and with an (170) including a layer is formed on the organic, for the plurality (180) by depositing a material which can be use number bath 1308. In addition, hole (140) and a light-emitting layer (150) light emitting [...] (151) is, light emitting layer (150) and alkali metal-containing fullerene (160) further can be formed between electronic transportation cadence layer.

In addition, various organic compound layer is formed polymer solution or solvent (solvent process) not a material deposition process, such as spin coating process, nozzle printing, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor steam turbines process, screen printing process, or thermal transfer method such as number of layer number can be by means of a high pressure liquid coolant. The present invention according to ITO layers can be formed into various method first, forming method of the present invention by the number range rights are not the.

In the embodiment according to materials used in the formed at each-emitting organic an electrical element can one of the present invention, can be a backlit or two-sided light emitting type.

And exhibits excellent processability for high resolution achieved by the WOLED (White Organic Light Emitting Device) is hereinafter, color filter is detected by the number of LCD can be bath...copyright 2001. White backlight device to perform various structures are mainly used as blue light emission and to perish patent number etc. and stored. Typically, R (Red), G (Green), B (Blue) light emitting portions disposed in parallel each other in a way that the (side provided by a-side), R, G, B down (stacking) and luminescent layer lamination scheme, blue (B) and inorganic phosphor converts the organic electro-luminescent in luminous layer therefrom light (photo-a luminescence) material (color conversion material, CCM) such as using the gamut to the ends of the first, also be applied to the present invention refers to such WOLED S802.

In addition, in the embodiment according to one of the present invention organic an electrical element can organic electroluminescence device, organic solar cells, organic photoreceptor, organic transistor, one white lighting element can be monochrome or color.

In the embodiment of the present invention is device including an electrical component on the aforementioned of the present invention other organic display, the display device comprising a number plower number including electronic device can be a water level. The, current or future electronic device is wire communication terminal may be, of a mobile phone, PDA, electronic dictionary, PMP, remote control, navigation, game machine, various TV, all electronic device comprising the various personal computer or the like.

Hereinafter, according to one aspect of the present invention compounds are disclosed therein.

According to one aspect of the present invention represented by formula 1 is displayed to.

<Formula 1>

In said formula 1, which each symbol is defined as follows.

L¹ C is₆ - C₆₀ It will be biting, [leyn strangeness of which, preferably C₆ - C₃₀ It will be biting, [leyn of, more preferably C₆ - C₁₈ It will be biting, [leyn strangeness of which, illustratively phenyl, naphthalene, biphenyl, xylene, phenanthrene, triphenylene etc. disclosed.

L² And L³ Are each independently a single bond is; C₆ - C₆₀ It will be biting, [leyn of; the flue [...]; O, N, S, Si and at least one of the hetero atoms including C P₂ - C₆₀ A variety of [...]; and C₆ - C₆₀ C aromatic ring and₃ - C₆₀ Aliphatic ring fusion [...]; selected from the group consisting of.

L² And L³ When the [...], preferably C₆ - C₃₀ It will be biting, [leyn of, more preferably C₆ - C₁₈ It will be biting, [leyn strangeness of which, illustratively phenyl, naphthalene, biphenyl etc. disclosed. L² And L³ When heterocyclic is due, preferably C₂ - C₃₀ A variety of [...], C₂ - C₁₀ Ring heteroatoms which, illustratively pyridine, die [...] etc. disclosed.

Ar¹ To Ar⁵ Are each independently C₆ - C₆₀ Aryl; O, N, S, Se, Si and P including C hetero atoms selected from the group consisting of at least one₂ - C₆₀ A variety of [...]; fluorene diary; C₆ - C₆₀ C aromatic ring and₃ - C₆₀ Aliphatic ring fusion [...]; C₁ - C₅₀ Alkyl; C₂ - C₂₀ An alkenoic diary; C₂ - C₂₀ Of alkyne diary; C₁ - C₃₀ The alkoxylation group; and C₆ - C₃₀ With biting jade time selected from the group consisting of. But, Ar² And Ar³ In addition it will doze number encoded in cover.

Ar¹ To Ar⁵ When is it is an allyl, preferably C₆ - C₆₀ Aryl, more preferably C₆ - C₁₈ R of which, illustratively phenyl, naphthyl, biphenyl, xylene, phenanthrene, fluoranthene etc. disclosed. Ar¹ To Ar⁵ When heterocyclic is due, preferably C₂ - C₆₀[...] heteroatoms, more preferably C₂ - C₁₈ Ring heteroatoms which, illustratively the offending cycle, pyridine, indole, for treatment, carbazole, indole roca it will doze, it cuts trillion [phyu column die, die [...], die it cuts trillion the leno pen which it will count etc. disclosed. Ar¹ To Ar⁵ The flue is when they are five [leyn diaries, illustratively 9, 9 - methyl - 9H - fluorene, 9, 9 - diphenyl - 9H - fluorene, 9, 9' - with at all [phul base five [leyn cyber etc. disclosed. Ar¹ To Ar⁵ When fusion ring, e.g. 1, 2 - disclosed hereinafter be synchronized with it will be a gap claw hit benzene.

M and n are each an integer from 0 to 3.

R¹ And R² Are each independently deuterium; of tritium; halogen; cyano group; alkoxy carbonyl; C₆ - C₆₀ Aryl; fluorene diary; O, N, S, Se, Si and P including C hetero atoms selected from the group consisting of at least one₂ - C₆₀ A variety of [...]; C₆ - C₆₀ C aromatic ring and₃ - C₆₀ Aliphatic ring fusion [...]; C₁ - C₅₀ Alkyl; C₂ - C₂₀ An alkenoic diary; C₂ - C₂₀ Of alkyne diary; C₁ - C₃₀ The alkoxylation group; and C₆ - C₃₀ Selected from the group consisting of with biting jade time and, when m is 2 or more integer adjacent R¹ Each other forms a ring in combination can be, even when n is an integer 2 or more adjacent R² Each other forms a ring combination can be. M is an integer of 2 or more when a plurality of R¹ Are identical to each other or can be different and, n is an integer of 2 or more even when a plurality of R² To each be the same or different.

R¹ And R² When is it is an allyl, preferably C₆ - C₆₀ Aryl, more preferably C₆ - C₁₀[...] of which, illustratively phenyl, me [phu etc. disclosed.

Adjacent R¹ Each other and/or adjacent R² C ring formed each in combination₆ - C₆₀ Aromatic rings, fluorene, O, N, S, Se, Si and P including C hetero atoms selected from the group consisting of at least one₂ - C₆₀ N-heterocyclic, or C₆ - C₆₀ C aromatic ring and₃ - C₆₀ Aliphatic ring fusion [...] may be like, illustratively be benzene it will be a ring. Adjacent R¹ Each other and/or adjacent R² The mold each benzene ring are bonded to each other, these combined with benzene ring with naphthalene, phenanthrene or the like can be formed.

Ar¹ - Ar⁵ , R¹ , R² , L¹ - L³ , Adjacent R¹ An annular each in combination, and adjacent R² An annular each in combination is deuterated; halogen; C₁ - C₂₀ C phenyl or benzyl₆ - C₂₀ Of with allyl substituted or substituted or unsubstituted silane; C₁ - C₂₀ C phenyl or benzyl₆ - C₂₀ A substituted or unsubstituted to phosphine oxide with allyl of; a siloxane group; to boron; for germanium; cyano group; nitro; C₁ - C₂₀ Alkyl [...]; C₁ - C₂₀ The alkoxylation group; C₁ - C₂₀ Alkyl; C₂ - C₂₀ An alkenoic diary; C₂ - C₂₀ Of alkyne diary; C₆ - C₂₀ Aryl; substituted with deuterium C₆ - C₂₀ Aryl; fluorene diary; O, N, S, Se, Si and P including C hetero atoms selected from the group consisting of at least one₂ - C₂₀ A variety of [...]; C₃ - C₂₀ Of cyclo-alkyl; C₇ - C₂₀ Of aryl-alkyl; - N (R^a ) (R^b ); C₈ - C₂₀ Of biting alkene group; and Selected from the group consisting of one or more substituted can be further substituted.

- N (R^a ) (R^b ) In, R^a And R^b Are each independently C₆ - C₆₀ Aryl; fluorene diary; and O, N, S, Se, Si and at least one of the hetero atoms including C P₂ - C₆₀ A variety of [...]; can be selected from the group consisting of, R^a And R^b Deuterium is; halogen; C₁ - C₂₀ C phenyl or benzyl₆ - C₂₀ With allyl substituted or substituted or unsubstituted silane of; a siloxane group; to boron; for germanium; cyano group; nitro; C₁ - C₂₀ Alkyl [...]; C₁ - C₂₀ The alkoxylation group; C₁ - C₂₀ Alkyl; C₂ - C₂₀ An alkenoic diary; C₂ - C₂₀ Of alkyne diary; C₆ - C₂₀ Aryl; substituted with deuterium C₆ - C₂₀ Aryl; fluorene diary; O, N, S, Se, Si and P including C hetero atoms selected from the group consisting of at least one₂ - C₂₀ A variety of [...]; C₃ - C₂₀ Of cyclo-alkyl; C₇ - C₂₀ Of aryl-alkyl; and C₈ - C₂₀ Of biting alkene diary; can be further substituted one or more selected from the group consisting of substituted.

Preferably, represented by formula 2 may be displayed one of said formula 1 to formula 5 and, more preferably of formula 6 to purchasers to formula 10 may be displayed disclosed.

<Formula 2><formula 3>

<Formula 4><formula 5>

<Formula 6><formula 7><formula 8>

<Formula 9><formula 10>

In said formula 2 to formula 10, Ar¹ - Ar⁵ , R¹ , R² , L¹ - L³ , M and n are the same and each symbol such as defined in formula 1.

In said formula 1 to formula 10, L¹ One of the display can be represented by formula L1 provided 1 to formula L1 provided 7.

L1 provided 2><formula L1 provided 3><formula L1 provided 1><formula

L1 provided 5><formula L1 provided 6><formula L1 provided 7><formula L1 provided 4><formula

In said formula L1 provided 1 to formula L1 provided 7, each an integer of 0 to 4 a to c, d is an integer of 0 to 6, e is an integer of 0 to 5, f and g each integer number of 0 to 3, R³ To R⁵ Are each independently aryl; fluorene diary; O, N, S, Si and P including C hetero atoms selected from the group consisting of at least one₂ - C₆₀ A variety of [...]; C₃ - C₆₀ C aliphatic ring and₆ - C₆₀ An aromatic ring in a fusion [...]; C₁ - C₅₀ Alkyl; C₂ - C₂₀ An alkenoic diary; C₂ - C₂₀ Of alkyne diary; C₁ - C₃₀ The alkoxylation group; and C₆ - C₃₀ With biting jade time selected from the group consisting of, a plurality of R when 2 or more levels respectively to g³ To R⁵ Each be the same or different.

L¹ When the L1 provided 1, preferably L¹ One is a structure may be, R for structure³ , Or the like defined in a L1 provided 1 such as disclosed.

, ,

Preferably, in formula 1 to formula 10, Ar¹ To Ar⁵ For at least one of the formula 11 can be represented.

<Formula 11>

In said formula 11, which each symbol can be defined as follows.

Ar¹ , Ar⁴ And Ar⁵ When X is at least one of the formula 11 S, Se, O, C (R^c ) (R^d ) Or N (R^e ) And, Ar² And Ar³ When X is at least one of the formula 11 S, Se, O or C (R^c ) (R^d ) Are disclosed.

C (R^c ) (R^d ) And N (R^e ) In, R^c To R^e Are each independently C₆ - C₆₀ Aryl; fluorene diary; O, N, S, Si and P including C hetero atoms selected from the group consisting of at least one₂ - C₆₀ A variety of [...]; C₃ - C₆₀ C aliphatic ring and₆ - C₆₀ An aromatic ring in a fusion [...]; C₁ - C₅₀ Alkyl; C₂ - C₂₀ An alkenoic diary; C₂ - C₂₀ Of alkyne diary; C₁ - C₃₀ The alkoxylation group; and C₆ - C₃₀ With biting jade time selected from the group consisting of, R^c And R^d Is in combination with compound cyber carbon they can be formed.

L⁴ A single coupling; C₆ - C₂₀ It will be biting, [leyn of; the flue [...]; O, N, S, Si and at least one of the hetero atoms including C P₂ - C₂₀ A variety of [...]; and C₃ - C₂₀ C aliphatic ring and₆ - C₂₀ Selected from the group consisting of an aromatic ring in a fusion ring crossroad.

O is an integer between 0 and 3, p is integer number of 0 to 4, R⁶ And R⁷ Deuterium independently of each other; of tritium; halogen; cyano group; alkoxy carbonyl; C₆ - C₆₀ Aryl; fluorene diary; O, N, S, Si and P including C hetero atoms selected from the group consisting of at least one₂ - C₆₀ A variety of [...]; C₃ - C₆₀ C aliphatic ring and₆ - C₆₀ An aromatic ring in a fusion [...]; C₁ - C₅₀ Alkyl; C₂ - C₂₀ An alkenoic diary; C₂ - C₂₀ Of alkyne diary; C₁ - C₃₀ The alkoxylation group; and C₆ - C₃₀ Selected from the group consisting of with biting jade time and, when 2 or more levels on p o respectively, each of a plurality of R⁶ And R⁷ Each can be the same or different, when 2 or more integer p o on respectively, adjacent R⁶ Each other, adjacent R⁷ Each other forms a ring combination can be.

More preferably Ar¹ , Ar² And Ar⁵ And at least one of the formula 11, the implementation being S is X in said formula 11.

Ar¹ To Ar⁵ When at least one of said formula 11, preferably represented by formula 1 to formula 1 - 3 can be display one of formula 1 - 1.

In said formula 1 - 1 and formula 1 - 3, X is S, Se, O, C (R^c ) (R^d ) Or N (R^e ) And, in said formula 1 - 2, X is S, Se, O or C (R^c ) (R^d ) And, Ar¹ To Ar⁵ , L¹ To L³ , R¹ , R² , M and n are the same as those defined in said formula 1 such as symbol which, L⁴ , R^c To R^e , R⁶ , R⁷ , O and p is defined in said formula 11 and are the same.

Specifically, one of compounds can be represented by said formula 1.

Another aspect of the present invention, electrode number 1, number 2 electrode, and said number 1 and number 2 electrode formed between organic solvent including electrical elements number [...] substrate. The, said organic compound layer is formed as a raw material compound having said formula 1 to formula 10.

Preferably said organic compound layer is formed hole injection layer, hole transport layer, light emitting [...], light emitting layer, electronic [...], with an alkali metal-containing fullerene and at least one layer comprising a 1, said hole injection layer, hole transport layer, light emitting [...], light emitting layer, electronic [...], said compound with an alkali metal-containing fullerene and at least 1 species alone or in admixture of at least one compound 2 1 layer is provided with a multiple myelomas are included. More preferably, light-emitting layer and said organic compound layer is formed comprising light emitting cadence layer, containing the red phosphor and said light-emitting layer, said light emitting [...] containing said compounds with each other.

Another aspect of the present invention is, according to Claim 8 display device and said display device including electronic device including an electrical driving a water level a number organic [...] number which, preferably said organic an electrical element can organic electroluminescence device, organic solar cells, organic photoreceptor, organic transistor, and monochrome or white lighting element can be one.

In hereinafter, the present invention according to formula 1 in the embodiment of the electrical component with respect to the synthesis of compound number for example specifically described attainments organic and positive examples but, in the embodiment of the present invention is confined to not the.

Synthesis example

The present invention according to formula 1 is a compound such as compound 1 (final products) and reacting Sub 1 and Sub 2 is generated, the pieces are not correct.

Ar¹ To Ar⁵ , L¹ To L³ , R¹ , R² , M and n are the same as defined in formula 1 or the like.

1><reactive

I. Sub 1 synthesis of

1 is a compound synthesized by the reaction of said reactive Sub 1 of 2 path but, limited to are not correct. Hal¹ Is I, Br, Cl and, Hal² Is Br, Cl are disclosed.

2><reactive

In said reactive 2, amine (HN-a Ar² Ar³ ) Reactants applicant when the Korean registration patent number 10 - 1251451 call (2013. 04. 05 user publication of registration) disclosure to synthetic method was used.

Sub 1 particular embodiments belonging to synthesis of compound as follows.

1. Sub 1 - 1, Sub 1 - 83 Synthesis example

3><reactive

(1) Sub 1 a-III-a 1 synthesis

Diphenylamine (CAS Registry Number: 122 - 39 - 4) starting material (17. 24 g, 101. 87 mmol) in a toluene [...] (850 ml) to a seam sealing, 2, 8 a-dibromodibenzo [b,d] Thiophene (CAS Registry Number: 31574 - 87 - 5) (52. 27 g, 152. 81 mmol), Pd₂ (Dba)₃ (2. 80 g, 3. 06 mmol), 50% P (t- Bu)₃ (4. 0 ml, 8. 15 mmol), NaOt- Bu (29. 37 g, 305. 62 mmol) added with agitation-gate 70 °C. Reaction is complete CH₂ Cl₂ After extracting a MgSO on organic layer₄ After the resulting compound and concentrated to dry silicagel column and subsequent recrystallization product 28. 06 g (yield: 64%) are obtained.

(2) Sub 1 - 1 synthesis

Said [...] Sub 1 a-III-a 1 obtained in the synthesis (12. 22 g, 28. 39 mmol), toluene (200 ml), (CAS Registry Number: 62 - 53 - 3) aniline (2. 91 g, 31. 23 mmol), Pd₂ (Dba)₃ (0. 78 g, 0. 85 mmol), 50% P (t- Bu)₃ (1. 1 ml, 2. 27 mmol) NaO andt- Bu (8. 19 g, 85. 18 mmol) frame and-gate 40 °C with agitation. Reaction is complete CH₂ Cl₂ After extracting a MgSO on organic layer₄ After the resulting compound silicagel column chromatography and concentrated to dry after positive number is recrystallised product 10. 43 g (yield: 83%) by Congress.

(3) Sub 1 a-IV a-83 synthesis

Said Sub 1 a-III-a 1 obtained in the synthesis (14. 59 g, 33. 90 mmol) [...] a THF (120 ml) to a seam sealing, (4 a-chlorophenyl) boronic acid (CAS Registry Number: 1679 - 18 - 1) (5. 83 g, 37. 29 mmol), Pd (PPh₃ )₄ (1. 57 g, 1. 36 mmol), NaOH (4. 07 g, 101. 71 mmol), water (60 ml) added with agitation-gate 80 °C. Reaction is complete CH₂ Cl₂ After extracting a MgSO on organic layer₄ After the resulting compound and concentrated to dry silicagel column and subsequent recrystallization product 10. 34 g (yield: 66%) by Congress.

(4) synthetic Sub 1 - 83

Said obtained in the synthesis Sub 1 a-IV-a 83 (10. 34 g, 22. 38 mmol) aniline (CAS Registry Number: 62 - 53 - 3) to (2. 29 g, 24. 62 mmol), Pd₂ (Dba)₃ (0. 61 g, 0. 67 mmol), 50% P (t- Bu)₃ (0. 9 ml, 1. 79 mmol), NaOt- Bu (6. 45 g, 67. 14 mmol), toluene (160 ml) using adding said Sub 1 - 1 synthesis product 9. 40 g (yield: 81%) are obtained.

2. Sub 1 - 20 Synthesis example

4><reactive

(1) Sub 1 a-I-a 20 synthesis

Starting material (4 a-bromophenyl) boronic acid (CAS Registry Number: 5467 - 74 - 3) (15. 17 g, 75. 54 mmol) [...] a toluene (755 ml) to a seam sealing, N- Phenyldibenzo [b,d] Thiophen-a 2 a-amine (CAS Registry Number: 1300028 - 91 - 4) (20. 80 g, 75. 54 mmol), Pd₂ (Dba)₃ (2. 08 g, 2. 27 mmol), 50% P (t- Bu)₃ (2. 2 ml, 4. 53 mmol), NaOt- Bu (21. 78 g, 226. 61 mmol) added with agitation 100 °C-gate. Reaction is complete CH₂ Cl₂ After extracting a MgSO on organic layer₄ After the resulting compound and concentrated to dry silicagel column and subsequent recrystallization product 25. 68 g (yield: 86%) are obtained.

(2) Sub 1 a-II-a 20 synthesis

Said Sub 1 a-I-a 20 obtained in the synthesis (25. 68 g, 64. 97 mmol) [...] a THF (230 ml) to a seam sealing, 2, 4 a-dibromo-a 1 - (methylsulfinyl) benzene (CAS Registry Number: 1820757 - 87 - 6) (21. 30 g, 71. 46 mmol), Pd (PPh₃ )₄ (3. 00 g, 2. 60 mmol), NaOH (7. 80 g, 194. 90 mmol), water (115 ml) with agitation adding 80 °C-gate. Reaction is complete CH₂ Cl₂ After extracting a MgSO on organic layer₄ After the resulting compound and concentrated to dry silicagel column and subsequent recrystallization product 25. 12 g (yield: 68%) by Congress.

(3) Sub 1 a-III-a 20 synthesis

Said Sub 1 a-II-a 20 obtained in the synthesis (25. 12 g, 44. 18 mmol) [...] a triflic acid (58. 6 ml, 662. 74 mmol) at room temperature 24 hours on specified behind it agitated, pyridine aqueous solution (775 ml, pyridine: H₂ O=1:5) 30 minutes and a reflux stirring slowly enemy-gate. Reaction is complete CH₂ Cl₂ After extracting a MgSO on organic layer₄ After the resulting compound and concentrated to dry silicagel column and subsequent recrystallization product 11. 62 g (yield: 49%) are obtained.

(4) synthetic Sub 1 - 20

Said Sub 1 a-III-a 20 obtained in the synthesis (11. 62 g, 21. 66 mmol) to [1, 1' a-biphenyl] provided 4 provided amine (CAS Registry Number: 92 - 67 - 1) (4. 03 g, 23. 82 mmol), Pd₂ (Dba)₃ (0. 59 g, 0. 65 mmol), 50% P (t- Bu)₃ (0. 8 ml, 1. 73 mmol), NaOt- Bu (6. 24 g, 64. 98 mmol), toluene (150 ml) using 10 adding said Sub 1 - 1 synthesis product. 83 g (yield: 80%) are obtained.

3. Sub 1 - 28 Synthesis example

5><reactive

(1) Sub 1 a-I-a 28 synthesis

Starting material (3 a-bromonaphthalen provided 2 a-yl) boronic acid (CAS Registry Number: 1301205 - 62 - 8) (29. 33 g, 116. 90 mmol) diphenylamine (CAS Registry Number: 122 - 39 - 4) to (19. 78 g, 116. 90 mmol), Pd₂ (Dba)₃ (3. 21 g, 3. 51 mmol), 50% P (t- Bu)₃ (3. 4 ml, 7. 01 mmol), NaOt- Bu (33. 71 g, 350. 71 mmol), toluene (1170 ml) adding said Sub 1 a-I-a 20 using synthesis product 29. 34 g (yield: 74%) are obtained.

(2) Sub 1 a-II-a 28 synthesis

Said Sub 1 a-I-a 28 obtained in the synthesis (29. 34 g, 86. 50 mmol) 2, 4 a-dibromo-a 1 - (methylsulfinyl) benzene (CAS Registry Number: 1820757 - 87 - 6) to (28. 35 g, 95. 15 mmol), Pd (PPh₃ )₄ (4. 00 g, 3. 46 mmol), NaOH (10. 38 g, 259. 49 mmol), THF (300 ml), water (150 ml) adding said Sub 1 a-II-a 20 using synthesis product 24. 82 g (yield: 56%) by Congress.

(3) Sub 1 a-III-a 28 synthesis

Said Sub 1 a-II-a 28 obtained in the synthesis (24. 82 g, 48. 43 mmol) to triflic acid (64. 3 ml, 726. 48 mmol), pyridine aqueous solution (850 ml, pyridine: H₂ O=1:5) adding said Sub 1 a-III-a 20 using synthesis product 11. 63 g (yield: 50%) by Congress.

(4) synthetic Sub 1 - 28

Said Sub 1 a-III-a 28 obtained in the synthesis (11. 63 g, 24. 21 mmol) (CAS Registry Number: 14770 - 85 - 5) to 5 a-phenylthiophen provided 2 a-amine (4. 67 g, 26. 63 mmol), Pd₂ (Dba)₃ (0. 67 g, 0. 73 mmol), 50% P (t- Bu)₃ (0. 9 ml, 1. 94 mmol), NaOt- Bu (6. 98 g, 72. 62 mmol), toluene (170 ml) using 8 adding said Sub 1 - 1 synthesis product. 77 g (yield: 63%) are obtained.

4. Sub 1 - 44, Sub 1 - 96 Synthesis example

6><reactive

(1) Sub 1 a-III-a 44 synthesis

Starting material N- (p- Tolyl) dibenzo [b,d] Furan-a 4 a-amine (CAS Registry Number: 1609080 - 05 - 8) (33. 00 g, 120. 73 mmol) to 3, 7 a-dibromodibenzo [b,d] Thiophene (CAS Registry Number: 83834 - 10 - 0) (61. 94 g, 181. 09 mmol), Pd₂ (Dba)₃ (3. 32 g, 3. 62 mmol), 50% P (t- Bu)₃ (4. 7 ml, 9. 66 mmol), NaOt- Bu (34. 81 g, 362. 19 mmol), toluene (1000 ml) adding said Sub 1 a-III-a 1 using synthesis product 38. 07 g (yield: 59%) are obtained.

(2) synthetic Sub 1 - 44

Said Sub 1 a-III-a 44 obtained in the synthesis (10. 42 g, 19. 50 mmol) to indolo [3, 2, 1 -Jk] Carbazol-a 5 a-amine (CAS Registry Number: 1191512 - 09 - 0) (5. 50 g, 21. 45 mmol), Pd₂ (Dba)₃ (0. 54 g, 0. 58 mmol), 50% P (t- Bu)₃ (0. 8 ml, 1. 56 mmol), NaOt- Bu (5. 62 g, 58. 49 mmol), toluene (135 ml) using adding said Sub 1 - 1 synthesis product 9. 96 g (yield: 72%) are obtained.

(3) Sub 1 a-IV-a 96 synthesis

Said Sub 1 a-III-a 44 obtained in the synthesis (27. 50 g, 51. 45 mmol) to (5 a-chloropyridin provided 3 a-yl) boronic acid (CAS Registry Number: 872041 - 85 - 5) (8. 91 g, 56. 60 mmol), Pd (PPh₃ )₄ (2. 38 g, 2. 06 mmol), NaOH (6. 17 g, 154. 36 mmol), THF (180 ml), water (90 ml) adding said Sub 1 a-IV a-83 using synthesis product 14. 88 g (yield: 51%) by Congress.

(4) synthetic Sub 1 - 96

Said obtained in the synthesis Sub 1 a-IV-a 96 (14. 88 g, 26. 24 mmol) to 3 - (pyridin-a 3 a-yl) aniline (CAS Registry Number: 57976 - 57 - 5) (4. 91 g, 28. 86 mmol), Pd₂ (Dba)₃ (0. 72 g, 0. 79 mmol), 50% P (t- Bu)₃ (1. 0 ml, 2. 10 mmol), NaOt- Bu (7. 57 g, 78. 72 mmol), toluene (185 ml) using adding said Sub 1 - 1 synthesis product 9. 93 g (yield: 54%) are obtained.

5. Sub 1 - 46 and Sub 1 - 73 Synthesis example

7><reactive

(1) Sub 1 a-I-a 46 synthesis

Starting material (3 a-bromophenyl) boronic acid (CAS Registry Number: 89598 - 96 - 9) (38. 32 g, 190. 81 mmol) diphenylamine (CAS Registry Number: 122 - 39 - 4) to (32. 29 g, 190. 81 mmol), Pd₂ (Dba)₃ (5. 24 g, 5. 72 mmol), 50% P (t- Bu)₃ (5. 6 ml, 11. 45 mmol), NaOt- Bu (55. 02 g, 572. 42 mmol), toluene (1270 ml) adding said Sub 1 a-I-a 20 50 using synthesis product. 20 g (yield: 91%) are obtained.

(2) Sub 1 a-II-a 46 synthesis

Said Sub 1 a-I-a 46 obtained in the synthesis (50. 20 g, 173. 62 mmol) (methylsulfinyl) benzene (CAS Registry Number: 1638151 - 06 - 0) to 4 a-bromo-a 1 a-iodo-a 2 - (65. 89 g, 190. 98 mmol), Pd (PPh₃ )₄ (8. 03 g, 6. 94 mmol), NaOH (20. 83 g, 520. 85 mmol), THF (610 ml), water (305 ml) adding said Sub 1 a-II-a 20 using synthesis product 60. 21 g (yield: 75%) by Congress.

(3) Sub 1 a-III provided 46 and Sub 1 a-III-a 73 synthesis

Said Sub 1 a-II-a 46 obtained in the synthesis (60. 21 g, 130. 21 mmol) to triflic acid (115. 2 ml, 1302. 09 mmol), pyridine aqueous solution (1520 ml, pyridine: H₂ O=1:5) adding said Sub 1 a-III-a 20 synthesis using product Sub 1 a-III-a 46 23. 54 g (yield: 42%) and Sub 1 a-III-a 71 20. 73 g (yield: 37%) are obtained.

(4) synthetic Sub 1 - 46

Said Sub 1 a-III-a 46 obtained in the synthesis (11. 53 g, 26. 79 mmol) aniline (CAS Registry Number: 62 - 53 - 3) to (2. 74 g, 29. 47 mmol), Pd₂ (Dba)₃ (0. 74 g, 0. 80 mmol), 50% P (t- Bu)₃ (1. 0 ml, 2. 14 mmol), NaOt- Bu (7. 72 g, 80. 37 mmol), toluene (190 ml) using 10 adding said Sub 1 - 1 synthesis product. 08 g (yield: 85%) are obtained.

(5) synthesis Sub 1 - 73

Said Sub 1 a-III-a 73 obtained in the synthesis (10. 16 g, 23. 61 mmol) to [1, 1' a-biphenyl] provided 3 a-amine (CAS Registry Number: 2243 - 47 - 2) (4. 39 g, 25. 97 mmol), Pd₂ (Dba)₃ (0. 65 g, 0. 71 mmol), 50% P (t- Bu)₃ (0. 9 ml, 1. 89 mmol), NaOt- Bu (6. 81 g, 70. 82 mmol), toluene (165 ml) using adding said Sub 1 - 1 synthesis product 9. 80 g (yield: 80%) are obtained.

6. Sub 1 - 60 Synthesis example

8><reactive

Said Sub 1 a-III-a 46 obtained in the synthesis (11. 74 g, 27. 28 mmol) to dibenzo [b,d] Thiophen-a 2 a-amine (CAS Registry Number: 7428 - 91 - 3) (5. 98 g, 30. 01 mmol), Pd₂ (Dba)₃ (0. 75 g, 0. 82 mmol), 50% P (t- Bu)₃ (1. 1 ml, 2. 18 mmol), NaOt- Bu (7. 87 g, 81. 84 mmol), toluene (190 ml) using 10 adding said Sub 1 - 1 synthesis product. 63 g (yield: 71%) are obtained.

7. Sub 1 - 79 Synthesis example

9><reactive

(1) Sub 1 a-I-a 79 synthesis

Starting material (4 a-bromophenyl) boronic acid (CAS Registry Number: 5467 - 74 - 3) (22. 50 g, 112. 04 mmol) to N(CAS Registry Number: 90 - 30 - 2) - phenylnaphthalen provided 1 a-amine (24. 57 g, 112. 04 mmol), Pd₂ (Dba)₃ (3. 08 g, 3. 36 mmol), 50% P (t- Bu)₃ (3. 3 ml, 6. 72 mmol), NaOt- Bu (32. 30 g, 336. 11 mmol), toluene (1120 ml) adding said Sub 1 a-I-a 20 using synthesis product 35. 34 g (yield: 93%) are obtained.

(2) Sub 1 a-II-a 79 synthesis

Said Sub 1 a-I-a 79 obtained in the synthesis (35. 34 g, 104. 19 mmol) 1, 3 non-dichloro-a 2 - (methylsulfinyl) benzene (CAS Registry Number: 122199 - 98 - 8) to (23. 96 g, 114. 60 mmol), Pd (PPh₃ )₄ (4. 82 g, 4. 17 mmol), NaOH (12. 50 g, 312. 56 mmol), THF (360 ml), water (180 ml) adding said Sub 1 a-II-a 20 using synthesis product 25. 36 g (yield: 52%) by Congress.

(3) Sub 1 a-III-a 79 synthesis

Said obtained in the synthesis Sub 1 a-II-a 79 (25. 36 g, 54. 19 mmol) to triflic acid (71. 9 ml, 812. 80 mmol), pyridine aqueous solution (950 ml, pyridine: H₂ O=1:5) adding said Sub 1 a-III-a 20 using synthesis product 11. 10 g (yield: 47%) by Congress.

(4) synthetic Sub 1 - 79

Said Sub 1 a-III-a 79 obtained in the synthesis (11. 10 g, 25. 46 mmol) to dibenzo [b,d] Thiophen-a 4 a-amine (CAS Registry Number: 72433 - 66 - 0) (5. 58 g, 28. 01 mmol), Pd₂ (Dba)₃ (0. 70 g, 0. 76 mmol), 50% P (t- Bu)₃ (1. 0 ml, 2. 04 mmol), NaOt- Bu (7. 34 g, 76. 38 mmol), toluene (180 ml) using 10 adding said Sub 1 - 1 synthesis product. 37 g (yield: 68%) are obtained.

8. Sub 1 - 109, Sub 1 - 114, Sub 1 - 119 Synthesis example

10><reactive

(1) Sub 1 a-I-a 109 synthesis

Starting material (3 '- bromo - [1, 1' - biphenyl] - 3 a-yl) boronic acid (CAS Registry Number: 1048990 - 21 - 1) (73. 05 g, 263. 79 mmol) diphenylamine (CAS Registry Number: 122 - 39 - 4) to (44. 64 g, 263. 79 mmol), Pd₂ (Dba)₃ (7. 25 g, 7. 91 mmol), 50% P (t- Bu)₃ (7. 7 ml, 15. 83 mmol), NaOt- Bu (76. 06 g, 791. 38 mmol), toluene (1760 ml) adding said Sub 1 a-I-a 20 using synthesis product 86. 71 g (yield: 90%) are obtained.

(2) Sub 1 a-II-a 109 synthesis

Said obtained in the synthesis Sub 1 a-I-a 109 (86. 71 g, 237. 41 mmol) (methylsulfinyl) benzene (CAS Registry Number: 1638151 - 06 - 0) to 4 a-bromo-a 1 a-iodo-a 2 - (90. 09 g, 261. 15 mmol), Pd (PPh₃ )₄ (10. 97 g, 9. 50 mmol), NaOH (28. 49 g, 712. 22 mmol), THF (830 ml), water (415 ml) adding said Sub 1 a-II-a 20 95 using synthesis product. 88 g (yield: 75%) by Congress.

(3) Sub 1 a-III-a 109 synthesis

Said obtained in the synthesis Sub 1 a-II-a 109 (95. 88 g, 178. 05 mmol) to triflic acid (157. 6 ml, 1780. 50 mmol), pyridine aqueous solution (2080 ml, pyridine: H₂ O=1:5) adding said Sub 1 a-III-a 20 using synthesis product 36. 97 g (yield: 41%) by Congress.

(4) synthetic Sub 1 - 109

Said obtained in the synthesis Sub 1 a-III-a 109 (10. 21 g, 20. 16 mmol) to [1, 1' a-biphenyl] provided 4 provided amine (CAS Registry Number: 92 - 67 - 1) (3. 75 g, 22. 18 mmol), Pd₂ (Dba)₃ (0. 55 g, 0. 60 mmol), 50% P (t- Bu)₃ (0. 8 ml, 1. 61 mmol), NaOt- Bu (5. 81 g, 60. 48 mmol), toluene (140 ml) using adding said Sub 1 - 1 synthesis product 9. 47 g (yield: 79%) are obtained.

(5) synthesis Sub 1 - 114

Said obtained in the synthesis Sub 1 a-III-a 109 (10. 59 g, 20. 91 mmol) to dibenzo [b,d] Thiophen-a 2 a-amine (CAS Registry Number: 7428 - 91 - 3) (4. 58 g, 23. 00 mmol), Pd₂ (Dba)₃ (0. 57 g, 0. 63 mmol), 50% P (t- Bu)₃ (0. 8 ml, 1. 67 mmol), NaOt- Bu (6. 03 g, 62. 73 mmol), toluene (145 ml) using adding said Sub 1 - 1 synthesis product 9. 80 g (yield: 75%) are obtained.

9. Sub 1 - 119 Synthesis example

11><reactive

(1) Sub 1 a-IV-a 119 synthesis

Said obtained in the synthesis Sub 1 a-III-a 109 (15. 81 g, 31. 22 mmol) to (3 a-chlorophenyl) boronic acid (CAS Registry Number: 63503 - 60 - 6) (5. 37 g, 34. 34 mmol), Pd (PPh₃ )₄ (1. 44 g, 1. 25 mmol), NaOH (3. 75 g, 93. 65 mmol), THF (110 ml), water (55 ml) using 10 adding said Sub 1 a-IV a-83 synthesis product. 58 g (yield: 63%) by Congress.

(2) synthetic Sub 1 - 119

Said obtained in the synthesis Sub 1 a-IV-a 119 (10. 58 g, 19. 66 mmol) dibenzo [-b, d-] furan-a 4 a-amine (CAS Registry Number: 50548 - 43 - 1) to (3. 96 g, 21. 63 mmol), Pd₂ (Dba)₃ (0. 54 g, 0. 59 mmol), 50% P (t- Bu)₃ (0. 8 ml, 1. 57 mmol), NaOt- Bu (5. 67 g, 58. 98 mmol), toluene (140 ml) using adding said Sub 1 - 1 synthesis product 9. 29 g (yield: 69%) are obtained.

Sub 1 below can be a compounds belonging to such compounds, which are not limited to, table 1 Sub 1 some compounds belonging to the FD-a MS (Field Desorption provided Mass Spectrometry) represents the value are disclosed.

[Table 1]

II. Sub 2 synthesis of

1 reactive 11 is synthesized by the reaction of said reactive Sub 2 of path but, limited to are not correct. Hal³ The Br or I are disclosed.

12><reactive

In said reactive 11, amine (HN-a Ar⁴ Ar⁵ ) Reactants applicant when the Korean registration patent number 10 - 1251451 call (2013. 04. 05 user publication of registration) disclosure to synthetic method was used.

Sub 2 synthesis of compound belonging to particular embodiments as follows.

1. Sub 2 - 1 Synthesis example

13><reactive

Diphenylamine (CAS Registry Number: 122 - 39 - 4) starting material (7. 93 g, 43. 86 mmol) [...] a toluene (390 ml) after the melting, 1 a-bromo-a 3 a-iodobenzene (CAS Registry Number: 591 - 18 - 4) (19. 89 g, 70. 29 mmol), Pd₂ (Dba)₃ (1. 29 g, 1. 41 mmol), 50% P (t- Bu)₃ (1. 8 ml, 3. 75 mmol), NaOt- Bu (13. 51 g, 140. 58 mmol) added with agitation-gate 70 °C. Reaction is complete CH₂ Cl₂ After extracting a MgSO on organic layer₄ After the resulting compound and concentrated to dry silicagel column and subsequent recrystallization product 10. 48 g (yield: 69%) are obtained.

2. Sub 2 - 3 Synthesis example

14><reactive

Di - starting materialp- Tolylamine (CAS Registry Number: 620 - 93 - 9) (8. 76 g, 44. 40 mmol) to 1 a-bromo-a 3 a-iodobenzene (CAS Registry Number: 591 - 18 - 4) (18. 84 g, 66. 61 mmol), Pd₂ (Dba)₃ (1. 22 g, 1. 33 mmol), 50% P (t- Bu)₃ (1. 7 ml, 3. 55 mmol), NaOt- Bu (12. 80 g, 133. 21 mmol), toluene (370 ml) using 10 adding said Sub 2 - 1 synthesis product. 17 g (yield: 65%) are obtained.

3. Sub 2 - 4 Synthesis example

15><reactive

Diphenylamine (CAS Registry Number: 122 - 39 - 4) starting material (6. 31 g, 37. 29 mmol) to 3 a-bromo-a 5 a-iodo-a ' 1, 1 a-biphenyl (CAS Registry Number: 136649 - 44 - 0) (20. 08 g, 55. 93 mmol), Pd₂ (Dba)₃ (1. 02 g, 1. 12 mmol), 50% P (t- Bu)₃ (1. 5 ml, 2. 98 mmol), NaOt- Bu (10. 75 g, 111. 86 mmol), toluene (310 ml) using 10 adding said Sub 2 - 1 synthesis product. 90 g (yield: 73%) are obtained.

4. Sub 2 - 13 Synthesis example

16><reactive

Starting material N- Phenyldibenzo [b,d] Thiophen-a 2 a-amine (CAS Registry Number: 1300028 - 91 - 4) (9. 42 g, 34. 21 mmol) 1 a-bromo-a 3 a-iodobenzene (CAS Registry Number: 591 - 18 - 4) to (14. 52 g, 51. 31 mmol), Pd₂ (Dba)₃ (0. 94 g, 1. 03 mmol), 50% P (t- Bu)₃ (1. 3 ml, 2. 74 mmol), NaOt- Bu (9. 86 g, 102. 63 mmol), toluene (285 ml) using 10 adding said Sub 2 - 1 synthesis product. 31 g (yield: 70%) are obtained.

5. Sub 2 - 29 Synthesis example

17><reactive

Diphenylamine (CAS Registry Number: 122 - 39 - 4) starting material (4. 29 g, 25. 35 mmol) 2, 11 a-dibromotriphenylene (CAS Registry Number: 24253 - 51 - 8) to (14. 68 g, 38. 03 mmol), Pd₂ (Dba)₃ (0. 70 g, 0. 76 mmol), 50% P (t- Bu)₃ (1. 0 ml, 2. 03 mmol), NaOt- Bu (7. 31 g, 76. 05 mmol), toluene (210 ml) using adding said Sub 2 - 1 synthesis product 9. 02 g (yield: 75%) are obtained.

6. Sub 2 - 30 Synthesis example

18><reactive

Diphenylamine (CAS Registry Number: 122 - 39 - 4) starting material (7. 68 g, 45. 38 mmol) 1 a-bromo-a 4 a-iodobenzene (CAS Registry Number: 589 - 87 - 7) to (19. 26 g, 68. 07 mmol), Pd₂ (Dba)₃ (1. 25 g, 1. 36 mmol), 50% P (t- Bu)₃ (1. 8 ml, 3. 63 mmol), NaOt- Bu (13. 08 g, 136. 15 mmol), toluene (380 ml) using 10 adding said Sub 2 - 1 synthesis product. 59 g (yield: 72%) are obtained.

7. Sub 2 - 43 Synthesis example

19><reactive

Diphenylamine (CAS Registry Number: 122 - 39 - 4) starting material (6. 57 g, 38. 82 mmol) to 4 a-bromo-a 4 'a-iodo-a' 1, 1 a-biphenyl (CAS Registry Number: 105946 - 82 - 5) (20. 91 g, 58. 23 mmol), Pd₂ (Dba)₃ (1. 07 g, 1. 16 mmol), 50% P (t- Bu)₃ (1. 5 ml, 3. 11 mmol), NaOt- Bu (11. 19 g, 116. 47 mmol), toluene (325 ml) using 10 adding said Sub 2 - 1 synthesis product. 10 g (yield: 65%) are obtained.

8. Sub 2 - 52 Synthesis example

20><reactive

Starting material 4 - (dibenzo [b,d] Furan-a 2 a-yl) -N- Phenylaniline (CAS Registry Number: 1381976 - 37 - 9) (12. 46 g, 37. 15 mmol) 1 a-bromo-a 2 non-iodobenzene (CAS Registry Number: 583 - 55 - 1) to (15. 76 g, 55. 72 mmol), Pd₂ (Dba)₃ (1. 02 g, 1. 11 mmol), 50% P (t- Bu)₃ (1. 4 ml, 2. 97 mmol), NaOt- Bu (10. 71 g, 111. 45 mmol), toluene (310 ml) using adding said Sub 2 - 1 synthesis product 9. 66 g (yield: 53%) are obtained.

Sub 2 below can be a compounds belonging to such compounds, which are not limited to, table 2 is obtained from some compounds belonging to FD-a MS Sub 2 (Field Desorption provided Mass Spectrometry) are disclosed.

[Table 2]

III. Product synthesis

Sub 1 (1 equivalent) in a Toluene [...] seam sealing, Sub 2 (1 equivalent), Pd₂ (Dba)₃ (0. 03 equivalent), (t-a Bu)₃ P (0. 06 equivalent), NaOt-a Bu (3 equivalents) added with agitation 100 °C-gate. Reaction is complete CH₂ Cl₂ After extracting a MgSO on organic layer₄ Silicagel column and recrystallization of the final product and concentrated to dry after the resulting compound (final product) are obtained.

1. P-a 1 Synthesis example

21><reactive

Said Sub 1 - 1 obtained in the synthesis (3. 96 g, 8. 95 mmol) [...] a toluene (90 ml) to a seam sealing, Sub 2 - 1 (2. 90 g, 8. 95 mmol), Pd₂ (Dba)₃ (0. 25 g, 0. 27 mmol), 50% P (t- Bu)₃ (0. 3 ml, 0. 54 mmol), NaOt- Bu (2. 58 g, 26. 84 mmol) added with agitation 100 °C-gate. Reaction is complete CH₂ Cl₂ After extracting a MgSO on organic layer₄ After the resulting compound and concentrated to dry silicagel column and subsequent recrystallization product 5. 65 g (yield: 92%) are obtained.

2. P-a 20 Synthesis example

22><reactive

Said Sub 1 - 20 obtained in the synthesis (3. 81 g, 6. 10 mmol) Sub 2 - 13 to (2. 62 g, 6. 10 mmol), Pd₂ (Dba)₃ (0. 17 g, 0. 18 mmol), 50% P (t- Bu)₃ (0. 2 ml, 0. 37 mmol), NaOt- Bu (1. 76 g, 18. 29 mmol), toluene (60 ml) using 5 adding said P-a 1 synthesis product. 11 g (yield: 86%) are obtained.

3. P-a 35 Synthesis example

23><reactive

Said obtained in the synthesis Sub 1 - 28 (4. 03 g, 7. 01 mmol) to Sub 2 - 29 (3. 33 g, 7. 01 mmol), Pd₂ (Dba)₃ (0. 19 g, 0. 21 mmol), 50% P (t- Bu)₃ (0. 2 ml, 0. 42 mmol), NaOt- Bu (2. 02 g, 21. 03 mmol), toluene (70 ml) adding said P-a 1 using synthesis product 4. 89 g (yield: 72%) are obtained.

4. P-a 40 Synthesis example

24><reactive

Said Sub 1 - 44 obtained in the synthesis (4. 67 g, 6. 58 mmol) to Sub 2 - 3 (2. 32 g, 6. 58 mmol), Pd₂ (Dba)₃ (0. 18 g, 0. 20 mmol), 50% P (t- Bu)₃ (0. 2 ml, 0. 39 mmol), NaOt- Bu (1. 90 g, 19. 74 mmol), toluene (65 ml) adding said P-a 1 using synthesis product 4. 97 g (yield: 77%) are obtained.

5. P-a 52 Synthesis example

25><reactive

Said Sub 1 - 46 obtained in the synthesis (3. 54 g, 8. 00 mmol) Sub 2 - 4 to (3. 20 g, 8. 00 mmol), Pd₂ (Dba)₃ (0. 22 g, 0. 24 mmol), 50% P (t- Bu)₃ (0. 2 ml, 0. 48 mmol), NaOt- Bu (2. 31 g, 24. 00 mmol), toluene (80 ml) using 5 adding said P-a 1 synthesis product. 42 g (yield: 89%) are obtained.

6. P-a 71 Synthesis example

26><reactive

Said Sub 1 - 60 obtained in the synthesis (4. 10 g, 7. 47 mmol) Sub 2 - 30 to (2. 42 g, 7. 47 mmol), Pd₂ (Dba)₃ (0. 21 g, 0. 22 mmol), 50% P (t- Bu)₃ (0. 2 ml, 0. 45 mmol), NaOt- Bu (2. 15 g, 22. 42 mmol), toluene (75 ml) using 5 adding said P-a 1 synthesis product. 33 g (yield: 90%) are obtained.

7. P-a 79 Synthesis example

27><reactive

Said Sub 1 - 46 obtained in the synthesis (3. 22 g, 7. 28 mmol) Sub 2 - 43 to (2. 91 g, 7. 28 mmol), Pd₂ (Dba)₃ (0. 20 g, 0. 22 mmol), 50% P (t- Bu)₃ (0. 2 ml, 0. 44 mmol), NaOt- Bu (2. 10 g, 21. 83 mmol), toluene (75 ml) adding said P-a 1 using synthesis product 4. 71 g (yield: 85%) are obtained.

8. P provided 85 Synthesis example

28><reactive

Said obtained in the synthesis Sub 1 - 73 (4. 06 g, 7. 83 mmol) to Sub 2 - 52 (3. 84 g, 7. 83 mmol), Pd₂ (Dba)₃ (0. 22 g, 0. 23 mmol), 50% P (t- Bu)₃ (0. 2 ml, 0. 47 mmol), NaOt- Bu (2. 26 g, 23. 48 mmol), toluene (80 ml) using 5 adding said P-a 1 synthesis product. 30 g (yield: 73%) are obtained.

9. P-a 89 Synthesis example

29><reactive

Said obtained in the synthesis Sub 1 - 79 (4. 23 g, 7. 06 mmol) Sub 2 - 30 to (2. 29 g, 7. 06 mmol), Pd₂ (Dba)₃ (0. 19 g, 0. 21 mmol), 50% P (t- Bu)₃ (0. 2 ml, 0. 42 mmol), NaOt- Bu (2. 04 g, 21. 19 mmol), toluene (70 ml) using 5 adding said P-a 1 synthesis product. 29 g (yield: 89%) are obtained.

10. P-a 96 Synthesis example

30><reactive

Said obtained in the synthesis Sub 1 - 83 (4. 65 g, 8. 97 mmol) to Sub 2 - 1 (2. 91 g, 8. 97 mmol), Pd₂ (Dba)₃ (0. 25 g, 0. 27 mmol), 50% P (t- Bu)₃ (0. 3 ml, 0. 54 mmol), NaOt- Bu (2. 58 g, 26. 90 mmol), toluene (90 ml) using 5 adding said P-a 1 synthesis product. 87 g (yield: 86%) are obtained.

11. P-a 101 Synthesis example

31><reactive

Said obtained in the synthesis Sub 1 - 96 (5. 52 g, 7. 88 mmol) to Sub 2 - 3 (2. 77 g, 7. 88 mmol), Pd₂ (Dba)₃ (0. 22 g, 0. 24 mmol), 50% P (t- Bu)₃ (0. 2 ml, 0. 47 mmol), NaOt- Bu (2. 27 g, 23. 63 mmol), toluene (80 ml) adding said P-a 1 using synthesis product 4. 90 g (yield: 64%) are obtained.

12. P-a 119 Synthesis example

32><reactive

Said obtained in the synthesis Sub 1 - 109 (5. 12 g, 8. 61 mmol) to Sub 2 - 1 (2. 79 g, 8. 61 mmol), Pd₂ (Dba)₃ (0. 24 g, 0. 26 mmol), 50% P (t- Bu)₃ (0. 3 ml, 0. 52 mmol), NaOt- Bu (2. 48 g, 25. 82 mmol), toluene (85 ml) using 5 adding said P-a 1 synthesis product. 56 g (yield: 77%) are obtained.

13. P-a 125 Synthesis example

33><reactive

Said Sub 1 - 114 obtained in the synthesis (5. 36 g, 8. 58 mmol) to Sub 2 - 1 (2. 78 g, 8. 58 mmol), Pd₂ (Dba)₃ (0. 24 g, 0. 26 mmol), 50% P (t- Bu)₃ (0. 3 ml, 0. 51 mmol), NaOt- Bu (2. 47 g, 25. 74 mmol), toluene (85 ml) using 5 adding said P-a 1 synthesis product. 29 g (yield: 71%) are obtained.

14. P-a 135 Synthesis example

34><reactive

Said obtained in the synthesis Sub 1 - 119 (5. 61 g, 8. 19 mmol) to Sub 2 - 1 (2. 66 g, 8. 19 mmol), Pd₂ (Dba)₃ (0. 23 g, 0. 25 mmol), 50% P (t- Bu)₃ (0. 2 ml, 0. 49 mmol), NaOt- Bu (2. 36 g, 24. 57 mmol), toluene (80 ml) using 5 adding said P-a 1 synthesis product. 17 g (yield: 68%) are obtained.

Some compounds of the present invention prepared by the number according to exemplary synthesis such as FD-a MS value is said to table 3 such as disclosed.

[Table 3]

In an exemplary synthesis of the present invention represented by said formula 1 are described but, they all are on a Buchwald non-Hartwig cross coupling reaction, Suzuki cross-a coupling reaction, Intramolecular acid a-induced cyclization reaction (J. Mater. Chem. 1999, 9, 2095.) or the like in addition to the substituents specified based embodiment except for a synthesis defined formula 1 other substituent (Ar¹ To Ar⁵ , L¹ To L³ , R¹ , R² , M and n) even if the reaction is coupled said that one skilled can easily understand are disclosed. For example, in reactive 1 Sub 1 and Sub 2 ->Final Product reaction, starting materials in reactive 2 ->Sub 1 a-I reaction, starting material ->Sub 1 a-III reaction, Sub 1 a-III ->Sub 1 reaction, Sub 1 a-IV ->Sub 1 reaction, Buchwald non-Hartwig cross coupling reaction starting materials in 12 ->Sub 2 reaction is based both reactive and, in reactive 2 Sub 1 a-I ->Sub 1 a-II reaction, Sub 1 a-III ->Sub 1 a-IV reaction is based and Suzuki cross-a coupling reaction, reactive 2 1 a-III Sub 1 a-II ->Sub Intramolecular acid a-induced cyclization reaction in reaction (J. Mater. Chem. 1999, 9, 2095.) is based. Specifically specified even if the goal is not substituted is bound to said reactions that will.

Number of the electrical component trillion phyengs (1 phyeng=3.954 square yards) organic

[In the embodiment 1] Green organic light-emitting device(Hole)

According to the method of the present invention compound transport layer material using conventional organic electroluminescent device small number-gate. First, ITO layer formed on the organic substrate (anode) 4, 4', 4 "- Tris [2 a-naphthyl (phenyl) amino] triphenylamine (hereinafter" 2 a-TNATA " by being shrewd, to) 60 nm thickness by vacuum deposition of a formed hole-injecting layer, a 60 nm thickness by vacuum deposition on said hole injection of the present invention compound P-a 1 weight percent a chemical formula. Then, hole on said 4, 4 '- N, N' - dicarbazole-a biphenyl (hereinafter, "CBP" by being shrewd, to) host material, tris (2 a-phenylpyridine) - iridium (hereinafter, " Ir (ppy)₃ " By being shrewd, to) dopant material in the weight ratio of 90:10 using vacuum deposition thickness 30 nm to form a luminescent layer by doping to him. Then on said light emitting layer (1, 1' - bis phenyl) - 4 - oleyl this toe) bis (2 - methyl - 8 - quinoline the [ley which comes the toe) aluminum (hereinafter "BAlq" by being shrewd, to) 10 nm thickness is formed by vacuum deposition of a hole a field oxidation, said hole obstruction layer tris (8 - quinolinol) aluminum (hereinafter " Alq₃ " By being shrewd, to) electronic vacuum deposition of a 40 nm thickness transporting bed weight percent. Then, a LiF halo [ceyn anger alkali metal 0. 2 nm thickness deposited electronic-injecting layer is formed, to a thickness of 150 nm by forming a negative electrode Al then depositing organic electroluminescent device number was high pressure liquid coolant.

[In the embodiment 2] to [In the embodiment 33] Green organic electroluminescent device (Hole)

Compounds of the present invention a compound of the present invention P-a 1 hole material on behalf bright 4 P-a 6 to the same method in the embodiment 1 and P-a 134 each using the point number [...] small number-gate organic electroluminescent device.

[Comparison example 1] to [Comparison example 6] Green organic electroluminescent device (Hole)

Transport layer material of the present invention to a comparison by the comparison compound 1 to compound P-a 1 bright 4 on behalf of each using the same method the number point 6 compounds and organic electroluminescent device small number-gate [...] said in the embodiment 1.

3><comparison compound 1><comparison compound 2><comparison compounds

4><comparison compound 5><comparison compound 6><comparison compounds

In the embodiment 33 of the present invention in the embodiment 1 and comparison example 1 to example 6 compared to allow the organic electroluminescent device prepared by the number by applying direct current to electroluminescent (EL) research (photoresearch) yarn is irradiated to measure characteristics when the PR-a 650, 5000 cd/m measurement² In reference number in parts of equipment when the measuring life through T95 [...] produced therewith, represented table 4 measurement such as disclosed.

[Table 4]

From the result of said table 4 you will, organic electroluminescent device of the present invention compound is used as a material hole hole using a comparison compound 1 compared to compound 6 degrees of organic electroluminescent element material which has a low driving voltage, and the like that are formed as well as making sure that the life can be improved.

Compounds of the present invention comparing compared compound 3 to 5 P-a 6 by solar heat, but they all have a same skeleton, core are different kind of atoms (S, C, N, O) is introduced, the core hole is different from atoms of different compound is used as a material when introduced to the outside can be informed that the color shift. The present invention S have been introduced such as core hole like when it cuts trillion be enveloped the pen thickness of the die is used as a material for organic electroluminescence device can be know that crucial.

This carbazole (in the embodiment 4) or die (in the embodiment 5) heterocyclic core die it cuts trillion be enveloped the pen when it cuts trillion [phyu column instead of introducing, to open the hole deep HOMO energy level and high refractive index material from same number since it became work element rises to the luminous efficiency and high light transmittance, deep HOMO energy level mobility of holes through fixing holes and the electrons by an increasing charge balance in the emissive layer of the light emitting time such as molding and has subsided substrate.

In addition, comparison example 3, example 4 comparison, comparison example 5 of the present invention in the embodiment and induced by comparing, when the atom is introduced on the same backbone heteroatoms can be remarkably improved efficiency life molecules. In particular, the present invention compound including carbon compounds such as 3 core when compared Sp3 exhibits lower thermal stability upon electroluminescent organic layer, directly between the organic layer, the organic layer metal electrode which occur among ten which it will pick up (Joule heat) heat resistance and resistance to high-temperature environment in making sure that the reduced first call request.

Comparison example 2 of the present invention compound (in particular P-a 1, P-a 6) comparing on induced by using in the embodiment, of the present invention in the embodiment driving voltage is lowered in the case of command and an indirectly-a remarkable improvement in the efficiency can be. Compounds of the present invention compound P-a 1 or 2 benzene ring framework of each die comprises a die [...] compared both P-a 6 amine (- N (C₆ H₆ )₂ ) Bonded to the substitution that provides the same or, in the case of compounds of the present invention and diphenyl amine substituted of phenyl amine substituted on one die back higher that are hereinafter disclosed. I.e., it cuts trillion be enveloped in the pen of the present invention in the embodiment such as die directly or indirectly coupled amine in substituent amine (- L¹ - NAr⁴ Ar⁵ ) Forms at least one hole is further substituted diamine type is used as a material when, the Pig tail and efficiency comparison example 2 molecules can be remarkably improved. This compound of the present invention substituted aryl amine compound 2 amine than comparison with substituent (- L¹ - NAr⁴ Ar⁵ ) In the introduction of a bend extending to unduly number by introducing appropriate range, the most suitable HOMO [...] HOMO energy level is adjusted hole hole [song layer an organic electroluminescence light emitting layer emitting energy level differences to permit charge balance an increase in better because in made to said substrate.

Comparison example 6 of the present invention in the embodiment and induced by comparing, in the case of comparison example 6 of the present invention in the embodiment emits a green light than head can be boosted. Comparison example 6 of the present invention in the embodiment and used in etched by using the compounds, compounds of the present invention and comparison compound 6 P-a 51, die it cuts trillion be enveloped in the pen P-a 58 coupled amine (- L³ - N (Ar² ) (Ar³ )) Ar in² Ar but have the same³ Only different structure can be know. I.e., compound 6 of the present invention compound P-a 51 all L and P-a 58 and comparison³ Single bond and, Ar² As phenyl is equal, Ar³ While compounds of the present invention cover the induction chain which will doze compared compounds are P provided 51 is phenyl, P-a 58 on each other die [...] hereinafter disclosed. Thus, even the same backbone substituted amine groups it cuts trillion be enveloped in the pen die core having such a structure in accordance with a classification, insulating layer exhibit a different result, Ar² And/or Ar³ Is carbazole (cover derivatives) phosphorous compound is used as a material of the present invention compound is used as a material with respect to hole hole when can be informed that a remarkable improvement in the luminous efficiency and lifespan. In particular, the present invention compound substituted amine substituted die cuts trillion is enveloped the pen to a substituted to amines used as hole material introduced P-a 58 substituted organic material a comparison compound introduced diazole cover hole 6 than at ends of the electrical component making sure that the luminous efficiency can be remarkably improved.

On the other hand, the present invention compounds of the sub-amine amine linkage connection between L¹ When the phenylene, insulating layer exhibits different results according to the engaged position. The present invention compound is P-a 1, P-a 6, P-a 11 can be by selecting a comparison, the present invention compound P-a 1, P-a 11 (meta) or five [lu meta phenylene amine is attached to locking position (ortho) while, P-a 6 (para) that is attached to a methyl para phenylene amine, these compounds as well as in the embodiment 1 is used as a material a hole (compound using P-a 1), and in the embodiment 6 in the embodiment 2 (compound using P-a 6) comparing (compound using P-a 11) by solar heat, efficiency and life is better in the embodiment 2 can be unworkable. The, linking group L¹ When the phenylene, amine compound to mate at the para-position to male and female hole can be more suitable for removing material. While, linking group L¹ When the phenylene, amine compounds are coupled to male and female mate than five [lu position meta or para-position with deep HOMO energy level a result amine compounds having five [lu derived more suitable material bonded to male and female [...] meta or position can be found.

In front described characteristics (high refractive index, high thermal stability, deep HOMO energy level) induced by a classifies the type of atoms (S, C, N, O) that is incorporated into a core and core (die [...]) amine substituted structure 2 to two amine substituted amine substituted aryl (- L¹ - NAr⁴ Ar⁵ ) Introduced in accordance with the kind of amine substituted and whether more band gap, electrical characteristics, characteristics largely varying in the interface that can be know, this major sidewalls of that acting can be confirmed.

If light emitting layer (host) surrounds a kernel of correlation with hole [...], similar core used in an effect by the present invention according to compound is used as a material hole representing relative to conventional art NaOCl is converted (features) belonging to ill afford the even are disclosed.

[In the embodiment 34] Red organic electroluminescent device (Light emitting [...])

Compounds of the present invention emitting organic electroluminescent device according to a conventional method O3 [...] small number-gate. First ITO layer (anode) formed on a glass substrate by vacuum deposition thickness 60 nm 2 provided TNATA formed hole-injecting layer, a hole injection layer on said vacuum deposition NPB 60 nm thickness by a chemical formula weight percent. Then, said compounds of the present invention has a thickness of 20 nm on the hole formed on the second P-a 1 vacuum deposition cadence layer, said light emitting [...] CBP on host material, bis - (1 a-phenylisoquinolyl) iridium (III) acetylacetonate (hereinafter " (piq)₂ Ir (acac)" by being shrewd, to) and dopant materials for use with 30 nm thickness by vacuum deposition to form a luminescent layer by doping was 95:5 by weight. Then, a 10 nm thickness on said light emitting layer is formed by vacuum deposition of BAlq hole a field oxidation, said hole obstruction layer Alq on₃ Electronic vacuum deposition of a 40 nm thickness transporting bed weight percent. Then, a LiF halo [ceyn anger alkali metal 0. 2 nm thickness deposited electronic-injecting layer is formed, to a thickness of 150 nm by forming a negative electrode Al then depositing organic electroluminescent device number was high pressure liquid coolant.

[In the embodiment 35] to [In the embodiment 104] Red organic electroluminescent device (Light emitting [...])

Light emitting [...] material of the present invention compound 5 of the present invention compound as a bright place P-a 1 P-a 2 to the point number in the embodiment 34 identical to the method using P-a 134 and [...] small number-gate organic electroluminescent device.

[Comparison example 7]

Light emitting cadence layer is concentrated and do not form a small number-gate organic electroluminescent device and method identical to the number [...] said in the embodiment 34.

[Comparison example 8] to [Comparison example 14]

A compound of the present invention P-a 1 5 bright light emitting [...] material on behalf as compared to comparison compound 8 to compound 2 each using the point number [...] the method identical to the organic electroluminescent device and said in the embodiment 34 small number-gate.

7><comparison compound 8><comparison compounds

In the embodiment 104 and comparison example 7 of the present invention in the embodiment 34 to allow the organic electroluminescent device prepared by the number by comparison to example 14 to electroluminescent (EL) to the photoresist applying direct current research (photoresearch) yarn PR provided 650 when the measurement, measurement 2500 cd/m² In reference number in parts of equipment when the measuring life through T95 [...] produced therewith, represented table 5 measurement such as disclosed.

[Table 5]

From the result of said table 5 you will, compounds of the present invention emitting organic electroluminescent device using the comparison example 7 [...] material compared compared to the organic electroluminescent device of example 14 are formed on life are improved significantly.

As compared to the comparison example 7 do not form light emitting cadence layer, comparison compound 2 using 8 to 14 formed on light emitting cadence layer compared to comparison compound 8 for example, the present invention compounds of the present invention in the embodiment comprises a light-emitting efficiency of light emitting organic electroluminescent device of cadence layer formed P can be sure that the, in particular of the present invention in the embodiment according to command when crystalline luminous efficiency can be boosted.

Table 4 aforementioned as well as already said, core introduced (S, C, N, O) on the type of atoms, substituted amine to amine substituted structure of core 2 (die [...]) amine substituted aryl (- L¹ - NAr⁴ Ar⁵ ) And whether more introduced, as well as light emitting [...] hole types of amine substituted (phosphorescent red) to form the sidewalls of even major factor, high refractive index, 220R high T1 value in deep HOMO energy level of the light hole capable of efficiently charge balance within the operations hereinafter for aggregates and build up to determine the other.

In particular, the present invention compound substituted heterocyclic substituent among other things to amines such as substituents at the die [...] introducing substituents at the at least one substituted aryl or both when a to amines introduced at least one refractive index than fixed cover diazole, high Tg value and therefore is capable of making sure that the luminous efficiency and thermal stability.

On the other hand, the compound of the present invention plot evaluation result of the aforementioned number desirable device characteristics are described but applied only to one hole and light emitting [...] layer, compounds of the present invention may be filled with [song layer light emitting [...] synchronous section of the hole.

According to the present invention description is to exemplify the user connects to the more generally described, the present invention essentially having the properties of the present invention belonging to NaOCl consultation knowledge of various deformable inputted from deviating from a will. Thus, the specification in the embodiment the present invention is to define the disclosure but rather to explain the which, in the embodiment of the present invention by such range is defined in which event are not correct. Comprises a charging range of the present invention scope of protection must be interpreted by, the equivalent of the present invention technique is interpreted in a range including all rights should range.