ORGANIC LIGHT-EMITTING COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING SAME

24-11-2015 дата публикации
Номер:
KR1020150130797A
Принадлежит:
Контакты:
Номер заявки: 00-14-102057850
Дата заявки: 14-05-2014

[1]

Relates to luminescent organic compound the present invention refers to, thereby removed compound or hole injection layer to hole transport layer hole transporting material-soluble polymer resin compound comprises a converts a multicyclic structure relates to.

[2]

The organic light emitting display element on the substrate even element finally, plasma display panel (Plasma Display Panel) or inorganic electroluminescent (EL) display compared to and low voltage driving 10 V hereinafter, which comparatively small power consumption, is adventageous by an excellent combination of color, green, blue, red 3 color may indicate there is a recent next-generation display element of interest and are amount of data into of wet liquid to flow down.

[3]

Just, such organic OELD elements exhibiting such features permit the light inside the light-order infusion materials are form an intergranular boundary organic layer, of a hole transport material, luminescent material, an electron transport material, electron injection substance and efficient stable supporting material should be this preceding is one, unmounted a stable efficient organic layer fluxing use in an organic electroluminescence element, an ECS is developed material. not first conductive layer. Therefore, low voltage driving, high efficiency and good cycle having a new-material development objects' traces to desired in which the container has such continuously.

[4]

In particular, copper phthalocyanine (CuPc) conventional hole transporting material, MTDATA, 4, 4 '-bis [N-(1-naphthyl)-N-phenylamino] biphenyl (NPB), N, N' -phenyl-N, N '-bis (3-methyl phenyl)-(1, 1' -biphenyl)-4, 4'-diamines (TPD) but such as is known, or inorganic anion same is prevented from releasing with symmetrical force efficiency and service life and, and improving same having various substituents is respect to compound biting amine orgin but, still efficiency and long life to satisfy simultaneously but not enough to has one of the upper and lower surfaces.

[5]

Furthermore, the organic light emitting display element determining luminous efficiency emitting material having the causes most important. Light emitting material is current is used to gather widely fluorescent material, light emitting mechanism phosphor material on an ECS is developed theoretically luminous efficiency can be improved more and one of a method, the phosphor material reacting the mixture by the addition of current respect to which is doubly formed development, in particular a phosphorescent light-emitting host material is to date CBP is known and gas is fed into a tube, used as hosts BALq derivatives is an organic light emitting device comprising is publicly known.

[6]

However, organic light-emitting device using a phosphorescent light-emitting material a fluorescence material using circuit-than current efficiency becomes significantly high, a phosphorescent light-emitting material BAlq's host, such as CBP used material, compared to an element isolation oxide film using the phosphor materials in which the drive voltage is high and free from the great advantage in power efficiency, in addition, light emitting spectrum of incident light does not Mar the impact is returned to the above stage have more stable and, high-performance is desired in which the container has of the host material.

[7]

Therefore, the present invention refers to said to the discharge of the torch electrode so as to, emitting layer host material or hole transport material harder than of the existing method gradually simultaneously formed on the transistor region. compounds are provided.

[8]

Furthermore, the present invention refers to such luminescent organic compound by adopting luminous efficiency very good the active gas and a multicyclic structure..

[9]

The present invention refers to said to solve the, a luminescent organic compound represented by [formula 1] and a multicyclic structure including..

[10]

[Formula 1]

[11]

[12]

Said of the specific luminescent organic compound according to [formula 1] each feature is refers to for substituents.

[13]

Conventional luminescent organic compound the present invention according to hole transport materials or host phosphor compared to the material the luminous efficiency and good cycle property can be driven at low voltage and using the same the organic light emitting display element useful in a variety of display device based.

[14]

Figure 1 shows a one embodiment of the present invention also of organic electroluminescence device according to examples of structure. whose cross section.

[15]

Hereinafter, the present invention more specifically, ..

[16]

The present invention refers to of organic electroluminescence device used for organic layer relates to luminescent organic compound, a are represented by [formula 1], core framework introduced thereto to in the substituents light emitting host material or hole transport material used as the P-type semiconductor layer, life and delivers low voltage driving is made possible is characterised in that it has a.

[17]

[Formula 1]

[18]

[19]

[Formula 1] said each substituted as the next.

[20]

R1 and R2 hydrogen, deuterium, a substituted or unsubstituted carbon atoms 1 to 30 alkyl, a substituted or unsubstituted carbon atoms 5 to 50 aryl and a substituted or unsubstituted carbon atoms of 2 to 50 is selected in aryl.

[21]

Z the a substituted or unsubstituted carbon atoms 10 and heteroaromatic ring or more aromatic rings, preferably a [formula C1] to [formula C8] selected from the group consisting can be one.

[22]

[23]

Said in [formula C1] to [formula C8],

[24]

R 'hydrogen, deuterium, a substituted or unsubstituted carbon atoms 1 to 30 alkyl, a substituted or unsubstituted carbon atoms 5 to 50 aryl and a substituted or unsubstituted carbon atoms of 2 to 50 of which is selected from aryl, the integer of 1 to 8 m, R m is 2 each a length different from each' each other can be different and can equal to or, * a [formula 1] .site that bind to.

[25]

X1 to X8 are identical to each other or which differ from each other in, each is independently hydrogen, deuterium, a substituted or unsubstituted carbon atoms 1 to 30 alkyl, a substituted or unsubstituted carbon atoms 5 to 50 aryl, a substituted or unsubstituted alkenyl group of 2 to 30 carbon atoms, a substituted or unsubstituted carbon atoms to alkynyl of 2 to 30, substituted or beach carbon can 30 to 3 of alkyl, substituted or substituted and heterogeneous nuclear reactor O, N, S, and P at least one of 2 to 50 having at aryl, a substituted or unsubstituted alkoxy group 1 to 30 carbon atoms, a substituted or unsubstituted carbon atoms of 6 to 30 biting jade time , a substituted or unsubstituted carbon atoms of halogenic acid-carboxylic acid 30 to 1, a substituted or unsubstituted amine it will be biting of 5 to 30 carbon atoms, a substituted or unsubstituted carbon atoms 1 to 30 alkyl silyl group, a substituted or unsubstituted carbon atoms will be biting and it will be recorded of 5 to 30, and halogenated cyano group is selected in a vapor reactor are described.

[26]

Furthermore, X1 to X8 at least one which is marked as a chemical [formula A] or the input unit is engaged with a, or a [formula B] connected in is characterised in that it has a.

[27]

[28]

Said in [A formula] and [formula B], [formula 1] of said a * X1 to X8. site that bind to.

[29]

Said in [A formula] and [formula B],

[30]

L1 and L2 independently from each other a substituted or unsubstituted carbon atoms 30 to 1 1015 per square meter, a substituted or unsubstituted carbon atoms of 2 to 30 [...] , substituted or it became equipping annularitycarbon possibility[...] of 2 to 30, of 3 to 30 it became equipping annularity substituted or carbon possibility[...] , substituted or it became equipping annularitycarbon possibility 5 arylene groups of 5 to 50, substituted or it became equipping annularitycarbon possibility[...] of 50 to 2, 3 to 30 hour claw alkylcarbon possibilityit became equipping annularity substituted or substituted or one or more of 5 to 50 carbon possibilityit amalgamatedit became equipping annularitycarbon possibilityit became equipping annularity substituted or and 5 arylene groups of 3 to 30 hour claw alkyl of one or more of 2 to 50 carbon possibilityit became equipping annularity substituted or it amalgamatedit is selected, among [...] , 0 to 2 of the m and n the essence and , when 2 is m and n, plurality number L1 and L2 each other. which may be the same or different.

[31]

Ar1 to Ar3 equal to or different and each other, independently a substituted or unsubstituted carbon atoms 1 to 30 alkyl, a substituted or unsubstituted alkyl of 3 to 30 carbon atoms, a substituted or unsubstituted carbon atoms 5 to 50 aryl and substituted or substituted and heterogeneous nuclear reactor O, N, S, and P at least one of 2 to 50 having at is selected in aryl.

[32]

[Formula 1] said, in [A formula] and [formula B], Z, X1 to X8, R1 and R2, L1 and L2, Ar1 to Ar3 adjacent the other group of substituted and desired asynchronization a substituted, and by forming rings polycyclic rings or single of aromatics with can be, formed said alicyclic group, polycyclic rings or single of aromatics with N the carbon atoms in ring, selected from the group consisting O and S one or more of nuclear reactor can be substituted.

[33]

Furthermore, in said [formula 1] 'a substituted or unsubstituted' in 'substituted' the at least one further substituents 1 involve substituted, at least one said 1 deuterium the substituents, cyano group, to halogen, hydroxy, nitro, alkyl 1 to 24 carbon atoms, 1 to 24 carbon atoms of halogenated alkyl, alkenyl group of 1 to 24 carbon atoms, to alkynyl of 1 to 24 carbon atoms, alkyl of 1 to 24 carbon atoms, aryl 24 to 6 carbon atoms, aralkyl of 6 to 24 carbon atoms, aryl group of 2 to 24 carbon atoms, aralkyl of of carbon number 2 to 24, carbon atoms in 1 24 alkoxy group, alkyl amino group 1 to 24 carbon atoms, amino it will be biting of 1 to 24 carbon atoms, amino it will be biting of 1 to 24 carbon atoms, alkyl silyl group 88800 01291888 to 24 carbon atoms, 1 to 24 carbon atoms and will be biting and it will be recorded of with biting jade time of 1 to 24 is selected from the group consisting of.

[34]

Preferred embodiment of the present invention, [formula B] of said Ar3 has an [formula D1] to [formula D6] to selected from the group consisting can be one.

[35]

[36]

Said in [formula D1] to [formula D6],

[37]

The X O, S, CRR or NR (R the [formula 1] in R1 and R2 are as defined in) and, R "hydrogen, deuterium, a substituted or unsubstituted carbon atoms 1 to 30 alkyl, a substituted or unsubstituted carbon atoms 5 to 50 aryl, a substituted or unsubstituted carbon atoms 2 to 30 of alkenyl group, a substituted or unsubstituted carbon atoms 2 to 30 of alkynyl to, a substituted or unsubstituted carbon atoms 3 to 30 of alkyl, a substituted or unsubstituted carbon atoms 5 to 30 of alkenyl group, a substituted or unsubstituted carbon atoms 1 to 30 alkoxy group, a substituted or unsubstituted carbon atoms 6 to 30 of biting jade time , a substituted or unsubstituted carbon atoms 1 to 30 alkyl mote jade time , a substituted or unsubstituted carbon atoms 5 to 30 of biting mote jade time , a substituted or unsubstituted carbon atoms 1 to 30 of halogenic acid-carboxylic acid, a substituted or unsubstituted carbon atoms 5 to 30 of amine it will be biting , a substituted or unsubstituted carbon atoms 5 to 50 aryl, substituted or substituted and heterogeneous nuclear reactor O, N or S having carbon atoms 2 to 50 of aryl group, cyano group, nitro and halogen in and wherein the polymer is selected from, n the 1 to 8 integer of, said n is 2 R plurality of a length different from each" each other. which may be the same or different.

[38]

Said [formula D1] to [formula D6] in aryl of R substituent carbon aromatic ring "is coupled is not hydrogen or deuterium is, may be coupled, said plurality of R" one of a single joined are bonded to nitrogen atoms on the can be.

[39]

The present invention according to organic light-emitting compound is preferably intranasal [formula 1] to [formula 2] to [formula 65] selected from the group represented by which can be one compound. Just, thereby [formula 1] the not of range is limited.

[40]

[41]

[42]

[43]

[44]

Of the present invention preferred embodiment, said X1 to X8 only one said [formula A] and the input unit is engaged with a, the n is 1 or 2, said L1 a single coupled or, a [formula 1] to [formula 8] selected from the group consisting can be one. A [formula 1] to [formula 8] the aromatic ring of the carbon mat the. can be combined with the or deuterium.

[45]

[46]

Furthermore, [formula A] of said Ar1 and Ar2 equal to or different and each other, independently a substituted or unsubstituted carbon atoms to 6 24 aryl or a substituted or unsubstituted carbon atoms may it will be an allyl of 5 to 24.

[47]

The present invention according to organic light-emitting compound is preferably intranasal [formula 1] to [formula 66] to [formula 113] which selected from the group represented by can be one compound. Just, thereby [formula 1] the not of range is limited.

[48]

[49]

[50]

[51]

Diffusibility of a movable ion used in the present invention a specific example methyl, ethyl, writing profile, isopropenyl-writing, trityl this cow department , to sec-butyl, tert-butyl to, [...] , oh pushing, -iso, [...] group, [...] , [...] , [...] , tri-chloro methyl, trifluoromethyl phenylethers such as methyl of the radioactive part into contact with, said at least one deuterium atoms that hydrogen atoms in alkyl, halogen atom, hydroxy, nitro, cyano group, trifluoromethyl, silyl group (in this case "alkyl silyl group-" assembling and welding steps), substituted or unsubstituted alkoxyalkylated amino group (-NH2, -NH (R), -N (R ') (R "), wherein R, R' and R" are each independently carbon atoms 1 to 24 is (in this case "alkyl amino group" assembling and welding steps)), amino d anger , hydrazine to, hydra zone , carboxyl group, sulfonic group, phosphoric acid groups, alkyl 1 to 24 carbon atoms, 1 to 24 carbon atoms of halogenated alkyl, alkenyl group of 2 to 24 carbon atoms, to alkynyl of 2 to 24 carbon atoms, of alkyl 8880001 356888 to 24 carbon atoms, aryl 24 to 5 carbon atoms, aralkyl of 6 to 24 carbon atoms, 3 to 24 carbon atoms of an aryl group or biting alkyl crossroad of 3 to 24 carbon atoms can be substituted.

[52]

Used in the present invention by one membered the organic radical as derived from aromatic hydrocarbons, 5 to 7 won, preferably 5 or 6 won including a single or fused ring system which, when substituent is in allyl in addition said neighboring substituted fused together, further the cyclic (fused) can be.

[53]

allyl in set as said, phenyl, o-ITO-glass substrate, m-ITO-glass substrate, ITO-glass substrate-p, o- phenyl , m- phenyl , phenyl -p, [...] , [...] , [...] , neel respirator, indenyl, flue [...] , tetra [...] , [...] perylene, cro ferosenyl rigand, naphtha ferosenyl rigand, such as flue [...] can be mentionned aromatic group.

[54]

Furthermore, 1 also aryl said at least one further substituents can be substituted, at least one of an aryl group more particularly deuterium atoms that hydrogen atom, halogen atom, hydroxy, nitro, cyano group, silyl group, amino group (-NH2, -NH (R), -N (R ') (R "), R' and R", independently one of the other are carbon atoms 1 to 10 of R3 is, in this case "alkyl amino group" assembling and welding steps), amino d anger , hydrazine to, hydra zone , carboxyl group, sulfonic group, phosphoric acid groups, alkyl 1 to 24 carbon atoms, 1 to 24 carbon atoms of halogenated alkyl, alkenyl group of 1 to 24 carbon atoms, to alkynyl of 1 to 24 carbon atoms, alkyl of 1 to 24 carbon atoms, aryl 24 to 6 carbon atoms, aralkyl of 6 to 24 carbon atoms, aryl group of 2 to 24 carbon atoms, aralkyl of 2 to 24 carbon atoms can be conversion on the.

[55]

An alkoxy used in the present invention a specific example of the functional group reactive with epoxy so2ch2ch2ox, [...] , width time profile, this cow department[...] , sec-butyl jade time , [...] , oh wheat jade time -iso, such as [...] of the radioactive part into contact with, said substituent similar when diffusibility of a movable ion..

[56]

A halogen used in the present invention a specific example of a fluorine (F), chlorine (Cl), bromine (Br) as to the aromatic hydrocarbon.

[57]

Used in the present invention O- biting jade time aryl radical meaning, the is as described above and the defined in said membered, in set as phenoxy, [...] , do not sprout three Neel jade city , [...] , flue [...] , and as to the aromatic hydrocarbon the Neel jade city which is , includes in biting jade time hydrogen atoms in one or more further substituted..

[58]

thread reel used in the present invention a specific example trimethylsilyl, triethylsilyl, phenyl thread reel tree, tree [...] , [...] , the D phenyl methyl it will be recorded , silyl, the D phenyl vinyl it will be recorded , methyl [...] , dimethyl [...] as to the aromatic hydrocarbon.

[59]

Used in the present invention, a heterodyne to membered [formula 1] to [formula 10] selected from the group consisting can be one.

[60]

[61]

Said in [formula 1] to [formula 10],

[62]

T1 to T12 are identical to each other or different and, independently, C (R41), C (R42) (R43), N, N (R44), O selected from the group consisting S and may be one, T1 to T12 simultaneously supplies both when the carbon atoms, said R41 to R44 equal to or different and each other, each is independently hydrogen, deuterium, a substituted or unsubstituted carbon atoms 1 to 30 alkyl, a substituted or unsubstituted alkyl of 3 to 30 carbon atoms, a substituted or unsubstituted carbon atoms 5 to 30 aryl and substituted or substituted and heterogeneous nuclear reactor O, N, P or S of having 2 to 30 carbon atoms is selected in aryl.

[63]

Furthermore, according to the [formula 3] by any electron transfer in the resonance structure to derivative is represented by the following [formula 3-1] may include a.

[64]

[Formula 3-1]

[65]

[66]

[Formula 3-1] in said, T1 to T7 the [formula 5] to [formula 14] equal to as defined in the application.

[67]

According to the example a preferred embodiment of the present invention, said [formula 1] to [formula 10] in [formula 11] to operate close to the loop frequency can be selected.

[68]

[Formula 11]

[69]

[70]

[71]

[72]

In said [formula 11],

[73]

The X in said [formula 1] X1 to X8 and equal to the definition of, the m integer of 11 to 1, m is 2 or more plurality of X equal to or which differ from each other in each other, said [formula 1] may be connected to, substituted.

[74]

Furthermore, one aspect of the present invention other electrode number 1, number 2 electrode and said number 1 number 2 electrode and via an or more organic layer 1 made organic light emitting diode is provided, said said organic layer represented by [formula 1] the present invention according to at least luminescent organic compound may include one or more 1.

[75]

Furthermore, with luminescent organic compound said of the present invention organic layer hole injection layer, hole transport layer, hole injection function be used as a solvent for the function and hole transport layers functional layer, light emitting layer, electron transport layer and an electron injection at least one of may comprise an.

[76]

The, two or more elements of Ag, said number 2 electrode and said number 1 organic layer contains a light-emitting layer may include, host and dopant consists said luminescent layer, the luminescent organic compound according to [formula 1] of the present invention can be used as host. While, in the present invention said dopant with host the light emitting layer can be material is used. Said when includes a dopant host and a luminescent layer, conventional content of dopant to the host about 100 parts by weight of dispersed in the base, from about 0.01 to about 20 parts by weight can be selected in a range of.

[77]

Furthermore, two or more elements of Ag, said number 2 electrode and said number 1 a organic layer hole injection layer, hole transport layer, hole injection function functions simultaneously and hole transport layers may include functional layers which, said hole injection layer, hole transport layer, hole injection function and hole transport layers functional layer be used as a solvent for the function according to [formula 1] of the present invention may include a luminescent organic compound.

[78]

Hereinafter, the present invention according to embodiment one of organic electroluminescence device also thereby, the cold air flows as further described via the 1..

[79]

Figure 1 shows a also of the present invention indicating the structure of the organic light emitting display element as cross-sectional drawing, the present invention according to the organic light emitting display element anode (20), the hole transport layer (40), is used for covering a organic (50), the light takeout efficiency (60) and cathode (80) includes, as needed hole injection layer (30) and an electronic injection layer (70) may further comprise a pump for, 1 layer or addition thereof formed to an intermediate layer 2 has a plurality, and further forming a insulating layer is prevented from being damaged or electronic 2006 can be, characteristic of the device according to system and method for organic layer may further include any.

[80]

Also reference to 1 of the present invention organic light emitting diode and manufacturing method thereof to longitude and equal.

[81]

Is composed (10) anode electrode on top the anode coating substance (20) to form a. Here substrate (10) at conventional organic electroluminescence device user uses a substrate used in transparency, surface smoothness, easy-to-clean, and handling organic and resist water preferably substrate or transparent plastic substrate. And, for anode electrode layer is transparent and highly conductive indium tin oxide (ITO), zinc indium oxide (IZO), tin oxide (SnO2), use an such as zinc oxide (ZnO).

[82]

Said anode (20) adjacent to hole injection layer material spin coating or vacuum atmosphere the hole injection layer (30) is formed on. Next said hole injection layer (30) the hole transport layer on top of the spin coating or thermal deposition products and the hole transport layer (40) is formed on.

[83]

Said hole injection layer material typically used in the art is ramyon, is not limited specially may be used in, specific by way of example, 2-TNATA [4, 4 ', 4"-tris (2-naphthylphenyl-phenylamino)-triphenylamine], NPD[N, N' -di (1-naphthyl)-N, N '-diphenylbenzidine)], TPD[N, N' -diphenyl-N, N '-bis (3-methylphenyl)-1, 1' -biphenyl-4, 4 '-diamine], DNTPD[N, N' -diphenyl-N, N '-bis-[ 4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4, 4' -diamine] and fixing, the present invention according to [formula 1] compound, use can be made of,.

[84]

Furthermore, said hole [...] material as to the commonly used art, do not limited to, extracts of Barks of, for example, N, N '-bis (3-methyl phenyl)-N, N' -diphenyl-[ 1, 1-biphenyl]-4, 4 '-diamine (TPD) or N, N' -di (naphthalene-1-one)-N, N '- [...] (α-NPD) which fixing, compounds of the present invention according to [formula 1], use can be made of,.

[85]

Furthermore, said hole transport layer (40) is used for covering a organic on top of (50) is used for covering a organic said are stacked and (50) 2006 selectively on top of a vacuum deposition method (not shown), or spin coating method for growing thin films as. obstruction layer hole said inlet a cathode through the layer organic hole resides an element when the SPAN of life and HOMO (Highest Occupied Molecular Orbital) level found not to significantly efficiency very low while employing make serves the. At this time, hole inhibiting material used, but are not limited to, electron transport ability higher than compound while ionizing potential which are representative of a must having BAlq, BCP, can be or the like is used as an TPBI.

[86]

As the material used for the hole said layer and the ridge, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq2, OXD-7, Liq and [formula 501] to [formula 507] one selected from the group consisting but can be used, limited to not.

[87]

BAlq BCP Bphen

[88]

[89]

TPBI NTAZ BeBq2

[90]

[91]

OXD-7 Liq

[92]

[93]

[Formula 501] [Formula 502] [Formula 503]

[94]

[95]

[Formula 504] [Formula 505] [Formula 506]

[96]

[97]

[Formula 507]

[98]

[99]

Such the light takeout efficiency electronic 2006 (60) a vacuum deposition method, or spin coating method after depositing the through electronic injection layer (70) said electronic injection layer is formed (70) on top of a vacuum thermal deposition by cathode cathode display panel and Image-forming apparatus (80) formed by organic EL device is is unlikely to complete to. Excitation cathodes in a lithium metal for forming (Li), magnesium (mg), aluminum (Al), aluminum 2-chloroethyl (Al-Li), calcium (Ca), magnesium-indium (mg-In), magnesium-silver (mg-Ag) which fixing, front ITO order light emitting element is obtained, a transmissive liquid using IZO, use can be made of, cathode.

[100]

Said electron transport layer material is an electron injection electrode (Cathode) stably electrons injected from a, and that function to transport of publicly known as ID an electron transport material. Examples of of electron transport materials publicly known, quinoline derivatives, in particular tris (8- [...]) aluminum (Alq3), TAZ, Balq, beryllium bis (benzo [...] -10-octanoate) (beryllium bis (benzoquinolin-10-olate: Bebq2), ADN, [formula 401], [formula 402], oxadiazole derivatives a PBD, BMD, using a material such as such as BND may be loaded with.

[101]

[102]

TAZ BAlq

[103]

[104]

[Compound 401] [Compound 402] BCP

[105]

[106]

Furthermore, an electron transport layer used in the present invention to an organic represented by [formula C] said metallic compound film, i.e., tungsten alone or the light takeout efficiency. can be used as material.

[107]

[Formula C]

[108]

[109]

In said [formula C],

[110]

C the Y, N, selected from the group consisting O and S said M one of directly bonded to at and a portion of a single joined, C, N, one selected from the group consisting O and S said M coordinately bounded to includes a portion of a, said single joined and. are ligands a chelating by coordinate bond and having. M an alkali metal, alkali earth, aluminum (Al) or boron is atoms (B).

[111]

The OA said M and a single bond or a coordinate bond and having as ligands of 1, which oxygen has said O, said A the a substituted or unsubstituted carbon atoms 1 to 30 alkyl, a substituted or unsubstituted carbon atoms 5 to 50 aryl, a substituted or unsubstituted alkenyl group of 2 to 30 carbon atoms, a substituted or unsubstituted carbon atoms to alkynyl of 2 to 20, a substituted or unsubstituted alkyl of 3 to 30 carbon atoms, a substituted or unsubstituted carbon atoms of 30 to 5 substituted or substituted and heterogeneous nuclear reactor and alkenyl group O, S or N having 2 to 50 carbon atoms selected from the group consisting of aryl is one.

[112]

Furthermore, said M the alkali metal selected from m=1 including one metal when the, n =0 and, said M the alkali earth including one metal selected from m=1 an upper electrode is formed on, or n =1, or m=2, n =0 and, an upper electrode is formed on said M to a boron or aluminum is one of 3 to m=1, as either the 0 to 2 n satisfy an m+n=3.

[113]

Said 'a substituted or unsubstituted' in 'substituted' the deuterium, cyano group, to halogen, hydroxy, nitro, alkyl, alkoxy groups, alkyl amino group, amino it will be biting , hetero amino it will be biting , alkyl silyl group, will be biting and it will be recorded , biting jade time , aryl, or a heteroaryl, germanium, phosphorus and by boron one or more selected from the group consisting of 1, meaning that the substituents..

[114]

Furthermore, each said Y which differ from each other in equal to or, independently of each other a [formula C1] to [formula C39] selected from either can be limited to not.

[115]

[Formula C1] [Formula C2] [Formula C3]

[116]

[117]

[Formula C4] [Formula C5] [Formula C6]

[118]

[119]

[Formula C7] [Formula C8] [Formula C9] [Formula C10]

[120]

[121]

[Formula C11] [Formula C12] [Formula C13]

[122]

[123]

[Formula C14] [Formula C15] [Formula C16]

[124]

[125]

[Formula C17] [Formula C18] [Formula C19] [Formula C20]

[126]

[127]

[Formula C21] [Formula C22] [Formula C23]

[128]

[129]

[Formula C24] [Formula C25] [Formula C26]

[130]

[131]

[Formula C27] [Formula C28] [Formula C29] [Formula C30]

[132]

[133]

[Formula C31] [Formula C32] [Formula C33]

[134]

[135]

[Formula C34] [Formula C35] [Formula C36]

[136]

[137]

[Formula C37] [Formula C38] [Formula C39]

[138]

[139]

Said in [formula C1] to [formula C39],

[140]

R are identical to each other or which differ from each other in, each is independently hydrogen, deuterium, halogen, cyano group, a substituted or unsubstituted carbon atoms 1 to 30 alkyl, a substituted or unsubstituted carbon atoms to 6 30 aryl, a substituted or unsubstituted aryl group of 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group 1 to 30 carbon atoms, a substituted or unsubstituted alkyl of 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 30 carbon atoms, a substituted or unsubstituted alkyl amino group 1 to 30 carbon atoms, a substituted or unsubstituted carbon atoms 1 to 30 is silyl group, a substituted or unsubstituted carbon atoms of 6 to 30 amino it will be biting and a substituted or unsubstituted carbon atoms of which is selected from will be biting and it will be recorded of 6 to 30, or with an alkylene substituents adjacent [...][...] is connected can be and by forming rings or fused.

[141]

Can substituted carbon substituted or L 1 to 30 alkyl, a substituted or unsubstituted alkoxy group 1 to 30 carbon atoms, a substituted or unsubstituted carbon atoms to 6 30 aryl, a substituted or unsubstituted carbon atoms of 30 to 5 aryl and a substituted or unsubstituted carbon atoms of 30 to 5 of which is selected from alkyl, alkyl said L 1 to 20 carbon atoms, alkyl of 3 to 20 carbon atoms, aryl 40 to 6 carbon atoms, aryl of 3 to 20 carbon atoms, cyano group, halogen to, deuterium and hydrogen that is at least one selected from at least one further substituents is substituted 1, adjacent substituents with an alkylene or [...][...] is connected can be and by forming rings or fused.

[142]

Furthermore, the present invention according to the organic light emitting display element said organic layer contains a light-emitting layer, , said said luminescent layer [formula 1] represented by at least one organic emitter compound other than to further dopant at least one phosphor is characterised in that an including, applied organic light emitting diode is of the present invention are provided to the light emitting dopant, but are not limited to, , a [general formula A-1] to [general formula J-1] that is at least one selected from compounds represented by general 1 can be one or more compounds thereof.

[143]

[General formula A-1]

[144]

[145]

the M group 7, group 8, group 9, group 10, group 11, group 13, group 14, group 15 and 16 are selected from the group consisting of a, preferably Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Ag and Au is chosen from. Furthermore, said L1, L2 and L3 the ligand identical or different from each and independently controlling each video the one selected from the group consisting [formula D] but users can, limited to not. Furthermore, a metal ions, in the * in [formula D] M for representing a that bind to site (site).

[146]

[Formula D]

[147]

[148]

[149]

[150]

[151]

[152]

[153]

[154]

[155]

[156]

[157]

In said [formula D],

[158]

Each different from or the same as each other said R is independently hydrogen, deuterium, halogen, cyano group, a substituted or unsubstituted carbon atoms 1 to 30 alkyl, a substituted or unsubstituted carbon atoms to 6 50 aryl, a substituted or unsubstituted aryl of 5 to 50 carbon atoms, a substituted or unsubstituted alkoxy group 1 to 30 carbon atoms, a substituted or unsubstituted alkyl of 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 30 carbon atoms, a substituted or unsubstituted alkyl amino group 1 to 30 carbon atoms, a substituted or unsubstituted carbon atoms 1 to 30 alkyl silyl group, a substituted or unsubstituted carbon atoms of 6 to 30 amino it will be biting and a substituted or unsubstituted 6 to 30 carbon atoms selected from the group consisting of will be biting and it will be recorded can be one.

[159]

Said R 1 to 20 carbon atoms are each independently alkyl, alkyl of 3 to 20 carbon atoms, aryl 40 to 6 carbon atoms, aryl of 3 to 20 carbon atoms, cyano group, halogen to, deuterium and hydrogen that is at least one selected from at least one 1 further substituents can be substituted.

[160]

Furthermore, respectively adjacent said R [...] or alkylene, substituted is connected cycloaliphatic ring and single rings or multi annularity can be aromatic ring.

[161]

Adjacent said L [...] or with an alkylene substituents ring members spiro ring is connected can be and by forming rings or fused.

[162]

In one example, said dopant represented by [general formula A-1] more absorbents selected from compound a one can be limited to not.

[163]

[164]

[165]

[166]

[167]

[168]

[169]

[General formula B-1]

[170]

[171]

[General formula B-1] in said,

[172]

MA1 as defined in the [general formula A-1] of a metal ion the same as a catalyst system comprising at least one, in addition, YA11, YA14, YA15 and YA18independent each carbon atoms or nitrogen atomit shows, , YA12, YA13, YA16 and YA17 are each independently substituted or substituted carbon atoms, a substituted or unsubstituted nitrogen atoms, oxygen atoms, sulfur atom, LA11, LA12, LA13, LA14 prior each group, such as a defined which, QA11, QA12 the MA1 that bind to exhibits moiety containing sequences atoms.

[173]

[General formula B-1] said for assisting in the removal of the compounds represented by general structure but following, not limited to.

[174]

[175]

[176]

[177]

[General formula C-1]

[178]

[179]

[General formula C-1] in said,

[180]

MB1 as defined in the [general formula A-1] of a metal ion the same as exhibits, YB11, YB14, YB15 and YB18 are each independently indicates the carbon atoms or nitrogen atoms, YB12, YB13, YB16 and YB17 are each independently substituted or nonsubstituted carbon atoms, a substituted or unsubstituted nitrogen atoms, oxygen atoms, sulfur exhibits, LB11, LB12, LB13, LB14 from the linking methyl group, QB11, QB12 the MB1 that bind to exhibits moiety containing sequences atoms.

[181]

[General formula C-1] said for assisting in the removal of the compounds represented by general structure but following, not limited to.

[182]

[183]

[184]

[General formula D-1]

[185]

[186]

[General formula D-1] in said,

[187]

MC1 the [general formula A-1] as defined in the same as of a metal ion exhibits, RC11, RC12 hydrogen atom independently linear, 5 won together and the substituent, connected to a each other exhibits a substituent light having no, RC13, RC14 hydrogen atom to independently linear, 5 won together and the substituent, there is no of interconnecting exhibits a substituent, GC11, GC12 nitrogen atoms in independently linear, substituted or nonsubstituted carbon atoms exhibiting, LC11, LC12 from the linking group which, QC11, QC12 the MC1 that bind to exhibits moiety containing sequences atoms.

[188]

[General formula D-1] said for assisting in the removal of the compounds represented by general structure but following, not limited to.

[189]

[190]

[191]

[General formula E-1]

[192]

[193]

[General formula E-1] in said,

[194]

MD1 as defined in the [general formula A-1] of a metal ion the same as exhibits, GD11, GD12 nitrogen atoms independently from each other, substituted or substituted carbon atoms exhibiting, JD11, JD12, JD13 and JD14 and by forming rings 5 won to independently linear atoms required the exhibits group, LD11, LD12 the 2000.

[195]

[General formula E-1] said for assisting in the removal of the compounds represented by general structure but following, not limited to.

[196]

[197]

[General formula F-1]

[198]

[199]

[General formula F-1] in said,

[200]

ME1 as defined in the [general formula A-1] of a metal ion the same as exhibits, JE11, JE12 independently from each other and by forming rings 5 won exhibits group atoms required the, GE11, GE12, GE13 and GE14 nitrogen atoms independently from each other, substituted or substituted carbon atoms exhibiting, YE11, YE12, YE13 and YE14 nitrogen atoms independently from each other, substituted or substituted carbon atoms exhibits.

[201]

[General formula F-1] said for assisting in the removal of the compounds represented by general structure but following, not limited to.

[202]

[203]

[General formula G-1]

[204]

[205]

[General formula G-1] in said,

[206]

MF1 the [general formula A-1] the same as defined in the application exhibits metal ions.

[207]

LF11, LF12 and LF13 exhibits the connecting group, RF11, RF12, RF13 and RF14 the methyl group, RF11 and RF12, RF12 and RF13, RF13 and RF14 has individual interconnecting the ring can be formed in the, the RF1 and RF12, RF13 and RF14 is formed in 5-membered ring is a ring. In addition QF11, QF12 the MF1 that bind to exhibits moiety containing sequences atoms.

[208]

[General formula G-1] said for assisting in the removal of the compounds represented by general structure but following, not limited to.

[209]

[210]

[211]

[General formula H-1] [general formula H-2] [general formula H-3]

[212]

[213]

Said [general formula H-1] to [general formula H-3] in,

[214]

R11, R12 and R4 may be alkyl, aryl or hetero group substituted it will be biting ; adjacent to each other in addition, substituted fused ring can be formed in the, the q11, q12 as integer 0 to 4, preferably 0 to 2 can be is.

[215]

Furthermore, when q11, q12 is 2 to 4, each plurality of R11 and R12. which may be the same or different.

[216]

L1 as ligands that bind on the platinum, ortho-(ortho metal) forming complexes platinum of a ligand, box nitrogen hetero annularity ligands, diketone ligands, preferably halogen ligands, more preferably ortho-(ortho metal) forming complexes platinum of ligands that, bipyridyl ligand or a salicylidene is ligands.

[217]

n1 the integer of 0 to 3, preferably 0 and, m1 the 1 or 2 and preferably is 2.

[218]

Furthermore, said n1, m1 the general formula H-1 which appear as to be neutral, n and m, n and m it is preferable that the.

[219]

[General formula H-2] in said,

[220]

R21, R22, n2, m2, q22, L2 each said R11, R12, n1, m1, q12, L1 in the vertical direction is the same and, q21 the integer of 0 to 2, preferably 0.

[221]

[General formula H-3] in said,

[222]

R31, n3, m3, L3 said each R11, n1, m1, L1 in the vertical direction is the same and, q31 and a structure represented by formula the 0 to 8, 0 to 2 are preferably present in the salt, . is more preferred to set a 0.

[223]

Said [general formula H-1] to [general formula H-3] include of compounds that are of the specific, such as, but, not limited to.

[224]

[225]

[General formula I-1]

[226]

[227]

[General formula I-1] in said,

[228]

A ring, ring B, and a cyclic C ring D D to A any of the the ring 2 of ring may have a substituent or the exhibits a nitrogen-containing heterocycle, the ring, pill two remaining 2 which may have a substituent or the exhibits biting ring or biting ring , exhibits, ring A B ring and a, ring A C and/or cyclic ring and a ring and a back-substitutions are condensed in a D B can be. X1, X2, X3 and X4 dog 2 the any of the platinum atoms and atom the nitrogen coordinately bounded to, remaining 2 exhibits the carbon atoms or nitrogen atoms. Q1, Q2 and Q3 are each independently 2 is of atoms (stage) or bonding of yet, Q1, Q2 and Q3 simultaneously bond not represented. Z1, Z2, Z3 and Z4 determines which 2 exhibit coordinate bond and having dog, phase has a covalently bonded two remaining 2, exhibits oxygen atom or sulfur atom.

[229]

Said [general formula I-1] include of compounds that are of the specific, such as, but, not limited to.

[230]

[231]

[232]

[233]

[234]

[General formula J-1]

[235]

[236]

[General formula J-1] in said,

[237]

[General formula A-1] the M as defined in the same as a catalyst system comprising at least one of a metal ion, Ar1 substituted or unsubstituted ring structure of the and indicates the type of the, 2 that bind to said M of azomethine (azomethine) coupled in (-C=N-), nitrogen atoms bind to and said M each (N), said M as a whole that are joined in a left 3 to form ligand left 3.

[238]

Furthermore, in the C Ar1 Ar1 represented by ring structure exhibits and the carbon atoms constituting the. The R2 and in addition said R1, the same or can be different and can, respectively or unsubstituted alkyl or aryl group which, the L a representation ligand left 1.

[239]

[General formula J-1] in said, it is preferred that a the M Pt. Furthermore, as said Ar1, 5-membered ring, 6-membered ring and their condensation ventilation it is preferable that the selected from.

[240]

Said [general formula J-1] include of compounds that are of the specific, such as, but, not limited to.

[241]

[242]

[243]

[244]

Furthermore, said dopant said emitting layer host various addition and a host the dopant and various may include further material.

[245]

Furthermore, said hole injection layer, hole transport layer, electronic stop layer, light emitting layer, 2006, allow a thin film electronic injection layer for solidifying least one of the layers being an selected from process or solution deposition fashion may be formed with, the deposition fashion said wherein said each layer by forming a flat surface portion between the material used for the heating, etc. in a vacuum or low pressure through method, a film is formed by evaporation using a evaporator means, said process solution said each layer by forming a flat surface portion between the material used for the same, and a solvent inkjet printing, permeablity coating, screen printing, spray coating, dip coating, spin coating method such as method of forming a buffer layer on the through..

[246]

Furthermore, the present invention according to the organic light emitting display element flat panel display device, flexible display device, monochrome or white plane light source for white monochrome or and device selected from flexible lighting device may be used in the device.

[247]

Hereinafter, a preferred embodiment the present invention example thereby, the cold air flows rapidly and to reduce a memory further.. However, these embodiment relate more specifically, the present invention for, are range of the present invention that are not limited by the homogeneously distributed will nontrivial twiddle factors and to person with skill in the art.

[248]

Synthesis example 1. Formula 2 synthesis of

[249]

1-1e.g. synthesis. <1-a>Synthesis of

[250]

Known as a raw material of the 1 by <1-a>A have been synthesised.

[251]

[Known as a raw material of the 1]

[252]

[253]

<1-a>

[254]

2 L reactor via ammoxidation Wibro 2-benzene trough 90 g (446 mmol), 1-naphthalene boronic acid 92 g (535 mmol), 123.2 g (891 mmol) potassium carbonate, tetra kissing tree phenyl gun spin palladium 17.2 g (9 mmol), H2 O 180 ml, toluene 450 ml and 24 for inserting and removing 450 ml 1, 4-dioxane classified as a carcinogenic substance 2000 reflux time. Completion after concentrated under the reduced pressure the separating column <1-a>103 g is obtained. (87% yield)

[255]

1-2e.g. synthesis. <1-b>Synthesis of

[256]

Known as a raw material of the 2 by <1-b>A have been synthesised.

[257]

[Known as a raw material of the 2]

[258]

[259]

<1-b>

[260]

2 L reactor <1-a>103 g (413 mmol), triphenyl phosphine 325.2 g (1240 mmol) paste has better mouth feeling and 1000 ml benzene medium of 2000 reflux time 24. Reaction after the separating column concentrated under the <1-b>70 g a obtained. (Yield 57%)

[261]

1-3e.g. synthesis. <1-c>Synthesis of

[262]

Known as a raw material of the 3 by <1-c>A have been synthesised.

[263]

[Known as a raw material of the 3]

[264]

[265]

<1-c>

[266]

500 ml of reactor <1-b>19 g (87 mmol), methyl 5-bromo-2-32.8 g (96 mmol) benzoate mol % of a multifunctional crosslinking agent, copper powder 5.6 g (83 mmol), 18-crown-6-ether 4.6 g (82 mmol), 24.2 g (175 mmol) potassium carbonate input packet doesn't have any error, dichloro benzene doesn't have any error frames, 2000 reflux time 24. Reaction after dichloro benzene to remove the separating column <1-c>15 g is obtained. (Yield 52%)

[267]

1-4e.g. synthesis. <1-d>Synthesis of

[268]

Known as a raw material of the 4 by <1-d>A have been synthesised.

[269]

[Known as a raw material of the 4]

[270]

[271]

<1-d>

[272]

Dried under the nitrogen into the reactor 1000 ml <1-c>39 g (336 mmol) in 400 ml 0 °C for ease of application and doesn't have any error frames, methyl magnesium bromide 91 ml (336 mmol) is blended for. 3 2000 time after completion blended at room temperature. 0 °C completion after 30 minutes in 100 ml 2 N-HCl aqueous solution for inserting and removing 2000. Organic layer 20 ml hydrochloric acid and a 400 ml acetic acid directly concentrated within 3 doesn't have any error frames, stirring the reflux time. Doesn't have any error frames, excess water after completion 30 ingredient place the separating column filtration <1-d>14 g is obtained. (Yield 47%)

[273]

1-5e.g. synthesis. <1-e>Synthesis of

[274]

Known as a raw material of the 5 by <1-e>A have been synthesised.

[275]

[Known as a raw material of the 5]

[276]

[277]

<1-e>

[278]

500 ml reactor <1-d>14 g (34 mmol), bis it blooms but cola toe D step magnetron 10.4 g (41 mmol), palladium (II) chloride -1, 1'-bis (die [...]) pherocene 1.4 g (1 mmol), 6.7 g (68 mmol) potassium acetate, 140 ml toluene 10 for inserting and removing 2000 reflux time. The remaining solid after reaction of decompressing filtrate after a concentrated. The separating column <1-g>10.5 g obtained. (Yield 61%)

[279]

1-6e.g. synthesis. < 화학식 2>Synthesis of

[280]

Known as a raw material of the have been synthesised by < 화학식 2>RNG to 6.

[281]

[Known as a raw material of the 6]

[282]

[283]

< 화학식 2>

[284]

Alkylbenzene and trough 1-1 e.g. synthesis via ammoxidation Wibro 2-in 1-naphthalene boronic acid instead and 2-chloro-4-phenyl-quinazoline <1-e>Paste using the same method except for the synthesis of < 화학식 2>4.1 g obtained. (Yield 32%)

[285]

MS+ 537.22

[286]

Synthesis example 2. Formula 9 synthesis of

[287]

2-1e.g. synthesis. <2-a>Synthesis of

[288]

By 7 known as a raw material of the <2-a>A have been synthesised.

[289]

[Known as a raw material of the 7]

[290]

[291]

<2-a>

[292]

1-3 e.g. synthesis in 2-bromo 5-bromo-2-5 mol % of a multifunctional crosslinking benzoate instead [...] used in the range of the same method except the synthesis of <2-a>25.6 g is obtained. (Yield 71%)

[293]

2-2e.g. synthesis. <2-b>Synthesis of

[294]

Known as a raw material of the 8 by <2-b>A have been synthesised.

[295]

[Known as a raw material of the 8]

[296]

[297]

<2-b>

[298]

In 1-4 e.g. synthesis <1-c>Instead <2-a>Paste using the same method except for the synthesis of <2-b>28.6 g is obtained. (Yield 71%)

[299]

2-3e.g. synthesis. <2-c>Synthesis of

[300]

By 9 known as a raw material of the <2-c>A have been synthesised.

[301]

[Known as a raw material of the 9]

[302]

[303]

<2-c>

[304]

Dried 500 ml after layer is wet-the nitrogen into the reactor <2-b>28.6 g (97 mmol), signals fifth lens 300 ml amide dimethyl formamide. N-bromo [...] 28.4 g (97 mmol) then into the slowly to a reactor. 2000 time 4 at room temperature. After the reaction at room temperature if determination is brown and blended of styrene, divinyl benzene wherein the filtration of the slurry suspension the separating column <2-c>27.8 g is obtained. (Yield 91%)

[305]

2-4e.g. synthesis. <2-d>Synthesis of

[306]

By 10 known as a raw material of the <2-d>A have been synthesised.

[307]

[10 known as a raw material of the]

[308]

[309]

<2-d>

[310]

In 1-5 e.g. synthesis <1-d>Instead <2-c>Paste using the same method except for the synthesis of <2-d>32.4 g is obtained. (Yield 82%)

[311]

2-5e.g. synthesis. < 화학식 9>Synthesis of

[312]

Known as a raw material of the have been synthesised by < 화학식 9>RNG to 11.

[313]

[11 known as a raw material of the]

[314]

[315]

< 화학식 9>

[316]

Alkylbenzene and trough 1-1 e.g. synthesis via ammoxidation Wibro 2-in 1-naphthalene boronic acid instead and 2-chloro-4-phenyl-quinazoline <2-d>Paste using the same method except for the synthesis of < 화학식 9>3.5 g is obtained. (Yield 26%)

[317]

MS+ 537.22

[318]

Synthesis example 3. Formula 10 synthesis of

[319]

3-1e.g. synthesis. <3-a>Synthesis of

[320]

Known as a raw material of the 12 by <3-a>A have been synthesised.

[321]

[Known as a raw material of the 12]

[322]

[323]

<3-a>

[324]

Synthesis example 9-1-naphthalene define a shallow acid instead 1-1 in phenanthrene define a shallow is provided which uniformizes subcutaneous fat, used in the range of the same method except the synthesis of <3-a>31.2 g is obtained. (87% yield)

[325]

3-2e.g. synthesis. <3-b>Synthesis of

[326]

Known as a raw material of the 13 by <3-b>A have been synthesised.

[327]

[Known as a raw material of the 13]

[328]

[329]

<3-b>

[330]

In 1-2 e.g. synthesis <1-a>Instead <3-a>Paste using the same method except for the synthesis of <3-b>28.4 g is obtained. (Yield 67%)

[331]

3-3e.g. synthesis. <3-c>Synthesis of

[332]

By 14 known as a raw material of the <3-c>A have been synthesised.

[333]

[14 known as a raw material of the]

[334]

[335]

<3-c>

[336]

In 1-3 e.g. synthesis <1-b>Instead <3-b>Paste using the same method except for the synthesis of <3-c>20.7 g is obtained. (Yield 62%)

[337]

3-4e.g. synthesis. <3-d>Synthesis of

[338]

Known as a raw material of the 15 by <3-d>A have been synthesised.

[339]

[Known as a raw material of the 15]

[340]

[341]

<3-d>

[342]

In 1-4 e.g. synthesis <1-c>Instead <3-c>Paste using the same method except for the synthesis of <3-d>32.4 g is obtained. (Yield 57%)

[343]

3-5e.g. synthesis. <3-e>Synthesis of

[344]

Known as a raw material of the 16 by <3-e>A have been synthesised.

[345]

[Known as a raw material of the 16]

[346]

[347]

<3-e>

[348]

In 1-5 e.g. synthesis <1-e>Instead <3-d>Paste using the same method except for the synthesis of <3-e>27.4 g obtained. (Yield 84%)

[349]

3-6e.g. synthesis. < 화학식 10>Synthesis of

[350]

Known as a raw material of the have been synthesised by < 화학식 10>RNG to 17.

[351]

[Known as a raw material of the 17]

[352]

[353]

< 화학식 10>

[354]

Alkylbenzene and trough 1-1 e.g. synthesis via ammoxidation Wibro 2-in 1-naphthalene boronic acid instead and 2-chloro-4-phenyl-quinazoline <3-e>Paste using the same method except for the synthesis of < 화학식 10>2.8 g obtained. (Yield 22%)

[355]

MS+ 587.24

[356]

Synthesis example 4. Formula 21 synthesis of

[357]

4-1e.g. synthesis. <4-a>Synthesis of

[358]

By 18 known as a raw material of the <4-a>A have been synthesised.

[359]

[Known as a raw material of the 18]

[360]

[361]

<4-a>

[362]

In 1-3 e.g. synthesis <1-b>And 5-bromo-2-5 mol % of a multifunctional crosslinking instead benzoate <3-b>And a 2-bromo benzoate using the method the same except for the host supplying the synthesis of <4-a>20.7 g is obtained. (Yield 62%)

[363]

4-2e.g. synthesis. <4-b>Synthesis of

[364]

Known as a raw material of the 19 by <4-b>A have been synthesised.

[365]

[Known as a raw material of the 19]

[366]

[367]

<4-b>

[368]

In 1-4 e.g. synthesis <1-c>Instead <4-a>Paste using the same method except for the synthesis of <4-b>31.5 g is obtained. (Yield 65%)

[369]

4-3e.g. synthesis. <4-c>Synthesis of

[370]

By 20 known as a raw material of the <4-c>A have been synthesised.

[371]

[Known as a raw material of the 20]

[372]

[373]

<4-c>

[374]

In 2-3 e.g. synthesis <2-b>Instead <4-b>Paste using the same method except for the synthesis of <4-c>24.3 g is obtained. (Yield 83%)

[375]

4-4e.g. synthesis. <4-d>Synthesis of

[376]

By 21 known as a raw material of the <4-d>A have been synthesised.

[377]

[21 known as a raw material of the]

[378]

[379]

<4-d>

[380]

In 1-5 e.g. synthesis <1-d>Instead <4-c>Paste using the same method except for the synthesis of <4-d>30.4 g is obtained. (Yield 82%)

[381]

4-5e.g. synthesis. < 화학식 21>Synthesis of

[382]

Known as a raw material of the have been synthesised < 화학식 21>for by 22.

[383]

[Known as a raw material of the 22]

[384]

[385]

< 화학식 21>

[386]

Alkylbenzene and trough 1-1 e.g. synthesis via ammoxidation Wibro 2-in 1-naphthalene boronic acid instead and 2-chloro-4-phenyl-quinazoline <4-d>Paste using the same method except for the synthesis of < 화학식 21>2.6 g is obtained. (Yield 31%)

[387]

MS+ 587.24

[388]

Synthesis example 5. Formula 24 synthesis of

[389]

5-1e.g. synthesis. <5-a>Synthesis of

[390]

By 23 known as a raw material of the <5-a>A have been synthesised.

[391]

[Known as a raw material of the 23]

[392]

[393]

<5-a>

[394]

Dried 2 L 6.8 g (282 mmol) magnesium reactor, Iriodin idle small amount, 200 ml tetrahydrofuran mixable 15 minutes under nitrogen doesn't have any error frames, 2000.2-bromo -9, 9-dimethyl -9H-fluorene 70 g (256 mmol) of tetra [...] 0 °C melt is blended in. About 2 time reflux stirring again in the state of in 0 °C alkylnitriles amino 2-15.4 g (128 mmol) of tetra [...]the enemy it inflicted melt after 2000 reflux time 2. In 0 °C 6 N-HCl aqueous solution after reaction 2.0 °C 2000 reflux time after the enemy it inflicted in fitted neutral blended aqueous solution 6 N-NaOH extracts the after the concentrated organic layer. The separating column <5-a>20 g is obtained. (Yield 52%)

[395]

5-2e.g. synthesis. <5-b>Synthesis of

[396]

By 24 known as a raw material of the <5-b>A have been synthesised.

[397]

[Known as a raw material of the 24]

[398]

[399]

<5-b>

[400]

500 ml reactor <5-a>34 g (108 mmol), urea 26 g (434 mmol), acetic acid 340 ml 12 doesn't have any error frames, 2000 reflux time. Reaction after excess precipitation into reactants to water ., followed by filtration. Methanol to the heated slurry wherein the filtration of the slurry suspension after drying the filtering the slurry the heated in toluene <5-b>15 g is obtained. (Yield 66%)

[401]

5-3e.g. synthesis. <5-c>Synthesis of

[402]

Known as a raw material of the 25 by <5-c>A have been synthesised.

[403]

[Known as a raw material of the 25]

[404]

[405]

<5-c>

[406]

300 ml reactor <5-b>15 g (44 mmol), phosphorous chloride 150 ml 3 doesn't have any error frames, 2000 reflux time. 0 °C excess water reactants to a reaction after precipitation into slowly ., followed by filtration. The separating column <5-c>12 g is obtained. (Yield 62%)

[407]

5-4e.g. synthesis. < 화학식 24>Synthesis of

[408]

Known as a raw material of the have been synthesised by < 화학식 24>RNG to 26.

[409]

[Known as a raw material of the 26]

[410]

[411]

< 화학식 24>

[412]

Synthetic e.g. antimony Wibro 2-1-1 in alkylbenzene and trough instead 1-naphthalene boronic acid <1-e>and a <5-c>Paste using the same method except for the synthesis of < 화학식 24>2.9 g is obtained. (Yield 29%)

[413]

MS+ 653.28

[414]

Synthesis example 6. Formula 39 synthesis of

[415]

6-1e.g. synthesis. <6-a>Synthesis of

[416]

Known as a raw material of the 27 by <6-a>A have been synthesised.

[417]

[27 known as a raw material of the]

[418]

[419]

<6-a>

[420]

Dried the nitrogen into the reactor 2 L layer is wet- roh acetate cyano ethyl after 139.8 g (1.236 mol), potassium cyanide 29.5 g (0.453 mol), potassium hydroxide 46.2 g (0.824 mol), amide dimethylformamide 20 minutes in 10 °C senses a rotation velocity of the disk 920 ml to 2000. 92 g (412 mol) then with naphthalene nitro 1-4 in 60 °C time doesn't have any error frames, 2000. Reaction after solvent is concentrated and and 10% sodium hydroxide aqueous solution 600 ml 1 doesn't have any error frames, 2000 reflux time. Filtered solid the separating column <6-a>50 g is obtained. (Yield 60%)

[421]

6-2e.g. synthesis. <6-b>Synthesis of

[422]

By 28 known as a raw material of the <6-b>A have been synthesised.

[423]

[Known as a raw material of the 28]

[424]

[425]

<6-b>

[426]

Dried 1 L after layer is wet-the nitrogen into the reactor <6-a>50.0 g (297 mmol), signals agitating the 500 ml amide dimethyl formamide. N-bromo [...] 55.56 g (312 mmol) then into the slowly to a reactor. 2000 time 4 at room temperature. Reaction after the player determination is brown blended of styrene, divinyl benzene at room temperature, is filtered and determined if the separating column <6-b>68 g is obtained. (Yield 93%)

[427]

6-3e.g. synthesis. <6-c>Synthesis of

[428]

By 29 known as a raw material of the <6-c>A have been synthesised.

[429]

[29 known as a raw material of the]

[430]

[431]

<6-c>

[432]

Synthetic e.g. antimony Wibro 2-1-1 in alkylbenzene and trough instead 1-naphthalene boronic acid <6-b>And a phenyl boron is provided which uniformizes subcutaneous fat, used in the range of the same method except the synthesis of <6-c>35.1 g is obtained. (Yield 81%)

[433]

6-4e.g. synthesis. <6-d>Synthesis of

[434]

By 30 known as a raw material of the <6-d>A have been synthesised.

[435]

[Known as a raw material of the 30]

[436]

[437]

<6-d>

[438]

Dried after the nitrogen into the reactor 2 L layer is wet-2-amino nitrile 45.0 g (381 mmol), for ease of application in 450 ml 0 °C doesn't have any error frames, phenyl magnesium bromide 250 ml (430 mmol) slowly after the enemy it inflicted 2000 reflux time 3. Ethyl [...] 30 g (225 mmol) senses a rotation velocity of the disk to 200 ml tetrahydrofuran mixable a blended slowly stirring to reflux time 2. Extracts the organic layer after completion, concentrating it under reduced pressure after the separating column <6-d>51 g is obtained. (Yield 78%)

[439]

6-5e.g. synthesis. <6-e>Synthesis of

[440]

Known as a raw material of the 31 by <6-e>A have been synthesised.

[441]

[Known as a raw material of the 31]

[442]

[443]

<6-e>

[444]

Synthetic e.g. 5-3 flowed in 25 of the <5-b>Instead obtained at the 30 known as a raw material of the <6-d>Paste using the same method except for the synthesis of <6-e>37 g obtained. (72% yield)

[445]

6-5e.g. synthesis. < 화학식 39>Synthesis of

[446]

Known as a raw material of the have been synthesised by < 화학식 39>RNG to 32.

[447]

[Known as a raw material of the 32]

[448]

[449]

< 화학식 39>

[450]

Synthetic e.g. antimony Wibro 2-1-1 in alkylbenzene and trough instead 1-naphthalene boronic acid <2-d>and a <6-e>Paste using the same method except for the synthesis of < 화학식 39>3.4 g obtained. (Yield 27%)

[451]

MS+ 663.27

[452]

Synthesis example 7. Formula 66 synthesis of

[453]

7-1e.g. synthesis. <7-a>Synthesis of

[454]

Known as a raw material of the 33 by <7-a>A have been synthesised.

[455]

[Known as a raw material of the 33]

[456]

[457]

<7-a>

[458]

2 L reactor biphenyl-4-amine 50.0 g (330 mmol), 2-bromo -9, 9-dimethyl -9H-fluorene 43.2 g (276 mmol), palladium acetate 1.2 g (5.6 mmol), 6.4 g (11.02 mmol) [...] , 126 g (386 mmol) cesium carbonate, 2000 reflux time 24 doesn't have any error frames, 1000 ml toluene. The cooled down to the normal temperature after completion of decompressing concentrate the toluene wherein the filtration of the slurry suspension. The separating column <1-d>57 g is obtained. (Yield 91%)

[459]

7-2e.g. synthesis. < 화학식 66>Synthesis of

[460]

Known as a raw material of the have been synthesised by < 화학식 66>RNG to 34.

[461]

[Known as a raw material of the 34]

[462]

[463]

< 화학식 66>

[464]

250 ml reactor <1-d>7.9 g (24.6 mmol), <7-a>8.3 g (30 mmol), palladium acetate 0.4 g (0.3 mmol), sodium tert [...] 4.2 g (43 mmol), tree tert butyl phosphine 0.1 g (0.3 mmol), 100 ml toluene for inserting and removing 2000 reflux time 13. Completion after separating column a concentrated methylene chloride and the methanol recrystallizing the < 화학식 66>4.0 g is obtained. (Yield 45%)

[465]

MS+ 692.32

[466]

Synthesis example 8. Formula 74 synthesis of

[467]

8-1e.g. synthesis. <8-a>Synthesis of

[468]

By 35 known as a raw material of the <8-a>A have been synthesised.

[469]

[Known as a raw material of the 35]

[470]

[471]

<8-a>

[472]

Tribromophenol reactor 500 ml benzene 25 g (79 mmol), phenyl [...] 23.3 g (191 mmol), 32.9 g (238 mmol) potassium carbonate, tetra kissing tree phenyl gun spin palladium 6.12 g (3 mmol), 50 ml distilled, toluene 125 ml and 1, 4-dioxane classified as a carcinogenic substance 24 of charging a 125 ml 2000 reflux time. Completion reactor after the bed, ., concentrating it under reduced pressure separated organic layer. The recrystallizing toluene and methanol <8-a>21 g a obtained. (85% yield)

[473]

8-2e.g. synthesis. <8-b>Synthesis of

[474]

Known as a raw material of the 36 by <8-b>A have been synthesised.

[475]

[Known as a raw material of the 36]

[476]

[477]

<8-b>

[478]

2-bromo -9, 9-dimethyl -9H 7-1 e.g. synthesis in instead-fluorene <8-a>Paste using the same method except for the synthesis of <8-b>14 g is obtained. (72% yield)

[479]

8-3e.g. synthesis. < 화학식 74>Synthesis of

[480]

Known as a raw material of the have been synthesised < 화학식 74>RNG to by 37.

[481]

[Known as a raw material of the 37]

[482]

[483]

< 화학식 74>

[484]

In 7-2 e.g. synthesis <1-d>and a <7-a>Instead <3-d>and a <8-b>Paste using the same method except for the synthesis of < 화학식 74>3.2 g is obtained. (Yield 19%)

[485]

MS+ 778.33

[486]

Synthesis example 9. Formula 98 synthesis of

[487]

9-1e.g. synthesis. <9-a>Synthesis of

[488]

Known as a raw material of the 38 by <9-a>A have been synthesised.

[489]

[Known as a raw material of the 38]

[490]

[491]

<9-a>

[492]

In instead biphenyl amino 4-7-1 e.g. synthesis of amino 2-except used in the range of the same method the synthesis of <9-a>17 g is obtained. (Yield 62%)

[493]

9-2e.g. synthesis. < 화학식 98>Synthesis of

[494]

Known as a raw material of the have been synthesised by < 화학식 98>RNG to 39.

[495]

[Known as a raw material of the 39]

[496]

[497]

< 화학식 98>

[498]

In 7-2 e.g. synthesis <7-a>Instead <9-a>Paste using the same method except for the synthesis of < 화학식 98>3.1 g is obtained. (Yield 28%)

[499]

MS+ 666.30

[500]

Synthesis example 10. Formula 106 synthesis of

[501]

10-1e.g. synthesis. <10-a>Synthesis of

[502]

Known as a raw material of the 40 by <10-a>A have been synthesised.

[503]

[Known as a raw material of the 40]

[504]

[505]

<10-a>

[506]

Synthesis of the 5 flowed in 1-5 e.g. <1-d>Instead [...] used in the range of 1-bromo-5-the same method except the synthesis of <10-a>63 g a obtained. (Yield 82%)

[507]

10-2e.g. synthesis. <10-b>Synthesis of

[508]

Known as a raw material of the 41 by <10-b>A have been synthesised.

[509]

[Known as a raw material of the 41]

[510]

[511]

<10-b>

[512]

Synthesis 1 of the flowed in 1-1 e.g. 1-naphthalene boronic acid instead obtained at the 40 known as a raw material of the <10-a>Paste using the same method except for the synthesis of <10-b>58.3 g a obtained. (Yield 86%)

[513]

10-3e.g. synthesis. <10-c>Synthesis of

[514]

Known as a raw material of the 42 by <10-c>A have been synthesised.

[515]

[Known as a raw material of the 42]

[516]

[517]

<10-c>

[518]

Synthesis 2 of the flowed in 1-2 e.g. <1-a>Instead obtained at the 41 known as a raw material of the <10-b>Paste using the same method except for the synthesis of <10-c>31 g for obtained. (Yield 64%)

[519]

10-4e.g. synthesis. <10-d>Synthesis of

[520]

Known as a raw material of the 43 by <10-d>A have been synthesised.

[521]

[Known as a raw material of the 43]

[522]

[523]

<10-d>

[524]

Synthetic e.g. 1-3 flowed in 3 of the <1-b>Instead obtained at the 42 known as a raw material of the <10-c>Paste using the same method except for the synthesis of <10-d>24.6 g a obtained. (Yield 62%)

[525]

10-5e.g. synthesis. <10-e>Synthesis of

[526]

Known as a raw material of the 44 by <10-e>A have been synthesised.

[527]

[44 known as a raw material of the]

[528]

[529]

<10-e>

[530]

Synthesis of the 4 flowed in 1-4 e.g. <1-c>Instead obtained at the 43 known as a raw material of the <10-d>Paste using the same method except for the synthesis of <10-e>20.4 g obtained. (72% yield)

[531]

10-6e.g. synthesis. <10-f>Synthesis of

[532]

Known as a raw material of the 45 by <10-f>A have been synthesised.

[533]

[Known as a raw material of the 45]

[534]

[535]

<10-f>

[536]

500 ml reactor <10-f>20.4 g (320 mmol), 20 g (276 mmol) hydrogen folktale Wibro, 2000 reflux time 15 doesn't have any error frames, 200 ml acetic acid. Extracts the completion after the concentrated organic layer. The separating column <10-f>18 g is obtained. (Yield 91%)

[537]

10-7e.g. synthesis. <10-g>Synthesis of

[538]

Known as a raw material of the 46 by <10-g>A have been synthesised.

[539]

[Known as a raw material of the 46]

[540]

[541]

<10-g>

[542]

500 ml reactor <10-f>18 g (52 mmol), 17.5 g (62 mmol) [...] anhydride, pyridine 4.9 g (62 mmol), methylene chloride 2000 time 5 doesn't have any error frames, 180 ml at room temperature. Extracts the completion after the concentrated organic layer. The separating column <10-g>22.8 g is obtained. (Yield 94%)

[543]

10-8e.g. synthesis. < 화학식 106>Synthesis of

[544]

Known as a raw material of the have been synthesised < 화학식 106>for by 47.

[545]

[Known as a raw material of the 47]

[546]

[547]

< 화학식 106>

[548]

In 7-2 e.g. synthesis <1-d>Instead <10-g>Paste using the same method except for the synthesis of < 화학식 106>2.1 g is obtained. (18% yield)

[549]

MS+ 692.32

[550]

In the embodiment 1to 6: organic of fabricating light emitting diodes

[551]

The cathode electrode is made of ITO glass of determined to be 2 mm × 2 mm after patterning cleaning section. Substrate after mounting for the lifetime of the vacuum chamber base pressure is 1 × 10-6 torr is the organic DNTPD (700 Å) on said ITO, NPD (300 Å), the present invention the compounds that are produced are by + RD-1 (10%) (300 Å), Alq3 (350 Å), LiF (5 Å), Al (1,000 Å) it does, made order of, was measured at 0.4 mA.

[552]

[553]

<DNTPD> <α-NPB>

[554]

[555]

<RD-1> < 화합물 E> <Liq>

[556]

Compared e.g. 1to 2

[557]

Compared e.g. a organic light emitting diode devices for said embodiment 1 the first deoxygenator device invention by instead and the compounds that are produced are generally phosphor host material using only one point using BAlq RH1 and the same except that the ratio said BAlq and a. following the structure of RH1.

[558]

[559]

<BAlq> <RH1>

[560]

Said in the embodiment 1 to 6, 2 to 1 compared e.g. an electrochemical method for organic light emitting diode is for, voltage, current density, luminance, color coordinates and the received data to determining the result showed to [table 1]. T95 initial luminance luminance (3000 cd/m2) reduced to 95% in. ports are.

[561]

Divided Host % Doping concentration V Cd/m2 CIEx CIEy T95 (Hr)
Compared example 1 BAlq 10 6.2 1470 0.665 0.334 40
Compared example 2 RH1 10 4.3 2100 0.665 0.334 110
In the embodiment 1 2 10 4.0 2310 0.665 0.335 224
In the embodiment 2 9 10 4.2 2350 0.664 0.335 185
In the embodiment 3 10 10 4.1 2230 0.665 0.334 187
In the embodiment 4 21 10 4.2 2360 0.665 0.334 216
In the embodiment 5 24 10 4.0 2300 0.666 0.333 191
In the embodiment 6 39 10 4.2 2390 0.665 0.334 220

[562]

[Table 1] said as in the present invention, can reliably ensure by host phosphorescent organic compounds are host consists of material BAlq material and is much more efficient than are and low driving voltage, RH1 than much improved life release properties.

[563]

In the embodiment 7: organic of fabricating light emitting diodes

[564]

The cathode electrode is made of ITO glass of determined to be 2 mm × 2 mm after patterning cleaning section. Substrate after mounting for the lifetime of the vacuum chamber base pressure is 1 × 10-6 torr DNTPD (700 Å) on said ITO for organic LED with a the pinion is, 66 (300 Å) and the compounds that are produced are by the present invention is formed on the front side in order, then, host BH1 BD1 3% dopant and mixing as the additive (250 Å) after compound E1: Liq = 1:1 (250 Å), Liq (10 Å), Al (1,000 Å) order of corresponding advertisement based on the shown list made, was measured at 0.4 mA.

[565]

In the embodiment 8to 10: organic of fabricating light emitting diodes

[566]

The present invention used in said in the embodiment 7 by reserving 66 and the compounds that are produced are are discussed in [table 2] to the region other than the provided which utilizes a equal to said in the embodiment 7 ratio organic electroluminescence device, the in light-emitting characteristics of organic electroluminescence device measured at 0.4 mA.

[567]

[568]

<BH1> <BD1>

[569]

Compared e.g. 3to 4

[570]

Invention 10 to said in the embodiment 7 in element structure using instead and the compounds that are produced are by the hole transport layer generally α-NPB using only one material HT1 and a point using the same except that the ratio said α-NPB HT1 and a. following the structure of.

[571]

[572]

<α-NPB> <HT1>

[573]

In the embodiment 7 to 10 compared e.g. made of 3 to 4 for organic light emitting diode is, voltage, current, luminance, color coordinates and the received data to determining the result showed to [table 2]. T80 luminance is initial brightness (3000 cd/m2) compared to ports are reduced to 80%.

[574]

Divided Hole transport compound V Cd/m2 CIEx CIEy T80 (Hrs) 3000 cd/m2
Compared example 3 Α-NPB 4.4 650 0.133 0.129 85
Compared example 4 HT1 4.2 730 0.150 0.150 110
In the embodiment 7 Formula 66 4.1 810 0.133 0.128 175
In the embodiment 8 Formula 74 4.2 790 0.132 0.126 180
In the embodiment 9 Formula 98 4.3 795 0.132 0.127 185
In the embodiment 10 Formula 106 4.3 770 0.132 0.127 170

[575]

Said as in [table 2], the present invention according to luminescent organic compound a hole transport layer and electrons are played back seamlessly on the basis of a transporter that transports the compound consists of material during α-NPB the electron transport is high in comparison with the thermal HT1 and have a long life.



[1]

The present invention relates to an organic light-emitting compound represented by chemical formula 1, and an organic electroluminescent device comprising the same. According to the present invention, the organic electroluminescent device employing an organic light-emitting compound as a host material in light-emitting layer of a device or a hole transport material of a hole injection layer and a hole transport layer, has more improved light-emitting efficiency and a long lifespan property than a host compound or a hole transport material which is conventionally employed and enables low-voltage drive.

[2]

COPYRIGHT KIPO 2016

[3]



A luminescent organic compound represented by [formula 1] : [formula 1] In said [formula 1], Z the a substituted or unsubstituted carbon atoms 10 more aromatic rings or heteroaromatic ring and, X1 to X8 are identical to each other or which differ from each other in, each is independently hydrogen, deuterium, a substituted or unsubstituted carbon atoms 1 to 30 alkyl, a substituted or unsubstituted carbon atoms 5 to 50 aryl, a substituted or unsubstituted alkenyl group of 2 to 30 carbon atoms, a substituted or unsubstituted carbon atoms to alkynyl of 2 to 30, substituted or beach carbon can 30 to 3 of alkyl, substituted or substituted and heterogeneous nuclear reactor O, N, S, and P at least one of 2 to 50 having at aryl, a substituted or unsubstituted alkoxy group 1 to 30 carbon atoms, a substituted or unsubstituted carbon atoms of 6 to 30 biting jade time , a substituted or unsubstituted carbon atoms of halogenic acid-carboxylic acid 30 to 1, a substituted or unsubstituted amine it will be biting of 5 to 30 carbon atoms, a substituted or unsubstituted carbon atoms 1 to 30 alkyl silyl group, a substituted or unsubstituted carbon atoms will be biting and it will be recorded of 5 to 30, and halogenated cyano group is selected from in, said X1 to X8 at least one which is marked as a chemical [formula A] or the input unit is engaged with a, or a [formula B] connected in is characterised in that an, Said in [A formula] and [formula B], [formula 1] of said a * X1 to X8 means site that bind to, L1 and L2 independently from each other a substituted or unsubstituted carbon atoms 30 to 1 1015 per square meter, a substituted or unsubstituted carbon atoms of 2 to 30 [...] , substituted or it became equipping annularitycarbon possibility[...] of 2 to 30, of 3 to 30 carbon possibilityit became equipping annularity substituted or [...] , substituted or it became equipping annularitycarbon possibility 5 arylene groups of 5 to 50, substituted or it became equipping annularitycarbon possibility[...] of 50 to 2, 3 to 30 hour claw alkylcarbon possibilityit became equipping annularity substituted or substituted or one or more of 5 to 50 carbon possibilityit amalgamatedit became equipping annularitycarbon possibilityit became equipping annularity substituted or and 5 arylene groups of 3 to 30 carbon possibilityit became equipping annularity substituted or it amalgamatedhour claw alkyl of one or more of 2 to 50 it is selected, among [...] , 0 to 2 of the m and n the essence and , when 2 is m and n, plurality number L1 and L2 each other which differ from each other in equal to or, Ar1 to Ar3 equal to or different and each other, independently a substituted or unsubstituted carbon atoms 1 to 30 alkyl, a substituted or unsubstituted alkyl of 3 to 30 carbon atoms, a substituted or unsubstituted carbon atoms 5 to 50 aryl and substituted or substituted and heterogeneous nuclear reactor O, N, S, and at least one P having at 50 to 2 of which is selected from aryl of, R1 and R2 hydrogen, deuterium, a substituted or unsubstituted carbon atoms 88 80002170888 to 30 alkyl, a substituted or unsubstituted carbon atoms 5 to 50 aryl and a substituted or unsubstituted carbon atoms of 2 to 50 of which is selected from aryl, Z, X1 to X8, R1 and R2, L1 and L2, Ar1 to Ar3 adjacent the other group of substituted and desired asynchronization a substituted, and by forming rings polycyclic rings or single of aromatics with can be, formed said alicyclic group, polycyclic rings or single of aromatics with N the carbon atoms in ring, S and selected from the group consisting O nuclear reactor one or more of which may be substituted, in said [formula 1] 'a substituted or unsubstituted' in 'substituted' the at least one further substituents 1 involve substituted, at least one said 1 deuterium the substituents, cyano group, to halogen, hydroxy, nitro, alkyl 1 to 24 carbon atoms, 1 to 24 carbon atoms of halogenated alkyl, alkenyl group of 1 to 24 carbon atoms, to alkynyl of 1 to 24 carbon atoms, alkyl of 1 to 24 carbon atoms, aryl 24 to 6 carbon atoms, aralkyl of 6 to 24 carbon atoms, aryl group of 2 to 24 carbon atoms, aralkyl of of carbon number 2 to 24, carbon atoms in 1 24 alkoxy group, alkyl amino group 1 to 24 carbon atoms, amino it will be biting of 1 to 24 carbon atoms, amino it will be biting of 1 to 24 carbon atoms, alkyl silyl group 1 to 24 carbon atoms, 1 to 24 carbon atoms and will be biting and it will be recorded of with biting jade time of 1 to 24 is selected from the group consisting of.

According to Claim 1, to said Z has an [formula C1] to [formula C8] selected from the group consisting sound absorbing member is partly characterized by luminescent organic compound: Said in [formula C1] to [formula C8], R 'in [formula 1] the R1 and R2 and equal to the definition of, the integer of 1 to 8 m, R m is 2 each a length different from each' each other can be different and can equal to or, * a [formula 1] .site that bind to.

According to Claim 1, [formula B] of said Ar3 enabled to operate close to the loop [formula D1] to [formula D6] selected from the group consisting sound absorbing member is partly characterized by luminescent organic compound: Said in [formula D1] to [formula D6], X the O, S, CRR or NR (R the [formula 1] in R1 and R2 are as defined in) and, R "hydrogen, deuterium, a substituted or unsubstituted carbon atoms 1 to 30 alkyl, a substituted or unsubstituted carbon atoms 5 to 50 aryl, a substituted or unsubstituted carbon atoms 2 to 30 of alkenyl group, a substituted or unsubstituted carbon atoms 2 to 30 of alkynyl to, a substituted or unsubstituted carbon atoms 3 to 30 of alkyl, a substituted or unsubstituted carbon atoms 5 to 30 of alkenyl group, a substituted or unsubstituted carbon atoms 1 to 30 alkoxy group, a substituted or unsubstituted carbon atoms 6 to 30 of biting jade time , a substituted or unsubstituted carbon atoms 1 to 30 alkyl mote jade time , a substituted or unsubstituted carbon atoms 5 to 30 of biting mote jade time , substituted or beach carbon possibility carbon can 1 to 30 of halogenic acid-carboxylic acid, a substituted or unsubstituted carbon atoms 5 to 30 of amine it will be biting , a substituted or unsubstituted carbon atoms 5 to 50 aryl, substituted or substituted and heterogeneous nuclear reactor O, N or S having carbon atoms 2 to 50 of aryl group, cyano group, nitro and halogen in and wherein the polymer is selected from, n the 1 to 8 integer of, said n is 2 R plurality of a length different from each" which differ from each other in equal to or each other, said [formula D1] to [formula D6] in aryl of R substituent carbon aromatic ring "is coupled is not hydrogen or deuterium is, may be coupled, said plurality of R" one of a single joined are bonded to nitrogen atoms on the can be.

According to Claim 1, said [formula 1] [formula 2] to [formula 65] to operate close to the loop frequency selected from the group represented by composition one characterized by luminescent organic compound:

According to Claim 1, said X1 to X8 only one said [formula A] and the input unit is engaged with a, the n is 1 or 2, said L1 a single coupled or, a [formula 1] to [formula 8] and one selected from the group consisting, a [formula 1] to [formula 8] the aromatic ring of the carbon mat the or deuterium is to be coupled that it may be set characterized by luminescent organic compound:

According to Claim 1, [formula A] of said Ar1 and Ar2 equal to or different and each other, independently a substituted or unsubstituted carbon atoms to 6 24 aryl or a substituted or unsubstituted carbon atoms to it is an allyl of 5 to 24 characterized by luminescent organic compound.

According to Claim 1, said [formula 1] [formula 66] to [formula 113] to operate close to the loop frequency represented by one selected from the group composition characterized by luminescent organic compound.

Number 1 electrode; a opposite to said number 1 number 2 electrode; and said number 1 electrode and an organic layer two or more elements of Ag, said number 2 ; includes, said organic layer anti number 7 to anti number 1 anti selected from the group consisting of luminescent organic compound according to at least one 1 to characterized by including the organic light emitting display element.

According to Claim 8, said organic layer hole injection layer, hole transport layer, light emitting layer, 2006, electron transport layer and an electron injection layer characterized by including at least more than one of said to the organic light emitting display element.

According to Claim 8, two or more elements of Ag, said number 2 electrode and said number 1 organic layer contains a light-emitting layer, , said dopant host and emitting layer which comprises an, anti number 7 to anti said number 1 selected from the group consisting anti according to organic light emitting compounds are as host characterized by be used for the organic light emitting display element.

According to Claim 8, said number 1 electrode and a organic layer two or more elements of Ag, said number 2 hole injection layer and hole transport layer encompasses at least one of the electrodes, said number 1 anti to number 7 anti selected from the group consisting anti according to organic light emitting compounds are hole injection layer or hole transport layer characterized by be used for the organic light emitting display element.

According to Claim 9, said organic layer deposition process or a solution, produced by means of to characterized by the organic light emitting display element.

According to Claim 8, the organic light emitting display element said flat panel display device, flexible display device, device and monochrome or white plane light source for monochrome or white flexible lighting device one selected from the group consisting device to be used for the organic light emitting display element characterized by.