TW201229203A - Electron transport material and organic electroluminescent device using the same - Google Patents

Abstract

This invention provides a compound of formula (1), which is characterized in being stable to voltage application even in a film state and having high charge transportability and suitably serves as a charge transport material of an organic electroluminescent (OEL) device. By applying the electron transport material to the electron transport layer and/or the electron injecting layer of an OEL device, the lifetime of the OEL device can be logner. In formula (1), Py is pyridyl, wherein arbitrary hydrogen may be replaced by alkyl, cycloalkyl, phenyl, 1-naphthyl or 2-naphthyl, and the phenyl, 1-naphthyl or 2-naphthyl may be substituted with alkyl or cycloalkyl. R is hydrogen, alkyl, cycloalkyl or aryl, wherein arbitrary hydrogen in the aryl may be replaced by alkyl or cycloalkyl.

Description

201229203 VI. Description of the Invention: [Technical Field] The present invention relates to a novel electron transporting device having a pyridyl group. The organic electroluminescent device (hereinafter referred to simply as an organic EL device) or simply referred to as Component) and so on. [Prior Art] In recent years, an organic EL device has been used as a next-generation full-color flat panel display, and it has been active research. In order to promote the practical use of organic EL components, the drive voltage of the components is reduced and the life is indispensable. = New electronic transport materials. It is necessary to realize the low cost and long life of the blue component. The patent document 丨 (Japanese Patent Laid-Open Publication No. 2 〇〇 23 23983) discloses that the 2,2,. of the morphine derivative or the analog thereof can be combined with the electron transfer electron (four), which can be low voltage _ organic anal = However, the characteristics of the elements reported in the examples of the literature (driving power efficiency, etc.) are only relative values which are based on comparative examples, and actual measured values which can be judged to be practical values are not described. In addition, the example of using 2, 2, ♦ to find a compound for electron transporting materials is taught in edingsQfthe (10) national Workshop on Inorganic and Organic ectrolu, in Patent Document 2 (Japanese Patent Special Reading _ ^8093) Bulletin) and Patent Document 3 (International Publication No. 2007/86552) disclose. The compound Tg described in Non-Patent Document 1 is low and is not practical. In the compounds described in Patent Documents 2 and 3, the organic EL device can be driven at a relatively low voltage, but it is expected to be further advanced in order to be long-lasting. [Prior Technical Paper] 4 201229203

.A

[Patent Document 1] Japanese Patent Laid-Open Publication No. JP-A-2002-123093 (Patent Document 2) Japanese Laid-Open Patent Publication No. 2002-158093 (Patent Document 3) International Publication No. 2007/86552 [Non-Patent Document] [Non-Patent Literature] 1] Proceedings of the 10th International

Workshop 〇n Inorganic and Organic Electroluminescence (2000) SUMMARY OF THE INVENTION The present invention has been made in view of the problems of the prior art. The subject of the present invention provides an electron transporting material which contributes to an extended life of an organic EL element and the like. Further, an object of the present invention is to provide an organic EL device using the electron transporting material. The inventors of the present invention have intensively studied and found that a compound having a pyridyl group on a phenyl group of 9-(1-naphthyl)-10-phenylindole can be used in an electron transporting layer of an organic EL device. The present invention has been completed based on this finding for an organic EL device that is driven for a long life. The above problems can be solved by the items shown below. Π] a compound represented by the following formula (1),

R is in the formula (1),

Py is. Any hydrogen in the acridinyl group may be a carbon number of 丨~6 alkane 201229203, a carbon number of 3 to 6 cycloalkyl groups, an alkyl group having a carbon number of i to 6 or a carbon number of 3 to 6 a cycloalkyl-substituted phenyl group, a 1-naphthyl group which may be substituted with an alkyl group having a carbon number of 66 or a cycloalkyl group having a carbon number of 3 to 6, or an alkyl group having a carbon number of 66 or a carbon number of 3 to 6 Substituted by a cycloalkyl-substituted 2-naphthyl group; R is hydrogen, an alkyl group having a number of 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or an aryl group having 6 to 14 carbon atoms, and any of the aryl groups The hydrogen may be substituted by an alkyl group having a carbon number of 66 or a cyclodext group having a carbon number of 3 to 6; moreover, at least one hydrogen in the compound of the formula (1) may be substituted by hydrazine.

[2] The compound according to [1], which is represented by the following formula (M) or (1-2), in the formulae (1-1) and (1-2),

Py is a pyridyl group, and any hydrogen in the pyridyl group may be an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms or a ring having 3 to 6 carbon atoms. An alkyl-substituted phenyl group, a 1-naphthyl group which may be substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms or a carbon number of 3 to 6 Substituted by a cycloalkyl-substituted 2-naphthyl group; R is hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or an aryl group having 6 to 14 carbon atoms, and any of the aryl groups Hydrogen may be substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms; moreover, at least one hydrogen of the compound of the formula (M) or (1-2) may be substituted by deuterium. [3] The compound according to [1] or [2], wherein Py is 2-acridinyl. [4] The compound according to [1] or [2], wherein Py is 3-pyridyl. 6 201229203, [5] The compound according to [1] or [2], wherein Py is 4 _ pyridine group. [6] The compound described in the item [1] or [2] wherein py It is one selected from the group of the following 1-valent groups.

[7] The compound according to the above [1] or [2], which is selected from the group consisting of the following formulas (1-1-1), (1-1-2), (1-1_3), (1- 1-134), (1-1-153), (1-1-172), (1-1-191), (1-1-21〇), (1_1_229), (1-2_1), (1 -2-153) and (1-2-172) one of the groups of the compounds listed,

201229203

[8] An electron transporting material, which comprises the compound according to any one of the above [1] to [7]. [9] An organic electroluminescence device comprising: a pair of electrodes including an anode and a cathode; a light-emitting layer disposed between the pair of electrodes; disposed between the cathode and the light-emitting layer and containing the above-mentioned item An electron transport layer and/or an electron injection layer of an electron transport material. [10] The organic electroluminescent device according to the above [9], wherein at least one of the electron transport layer and the electron injecting layer further contains a hydroxyquinoline-based metal complex, a bipyridine derivative, At least one of the group consisting of a phenanthroline derivative and a borane derivative. [11] The organic electroluminescent device according to [10], wherein at least one of the electron transport layer and the electron-injecting layer towel further comprises an oxide selected from the group consisting of a metal, a soil, a rare earth metal, an alkali metal, An alkali metal chemistry, an alkaline earth metal oxide, a geophysical metal dentate, a rare earth metal oxide, an 201229203 = compound, an alkali metal organic complex, and a soil-working metal complex. At least one of the groups. The compound of the invention has a feature of high transportability even in a film state, and is suitable as an organic a-component transport material. The compound of the present invention is used for or the electron injecting layer, and the organic EL device having a long life can be obtained with high performance such as full color display. [Embodiment] Hereinafter, the present invention will be described in more detail. In addition, in the present specification, for example, "the compound of the formula (1 small formula)" may be referred to as "compound (〗)])". The other chemical formula symbols and chemical formula numbers are treated in the same manner. The term "arbitrary" when defining a compound means that "not only the position but also the number can be freely selected." For example, the expression "any hydrogen in the phenyl group may be substituted by an alkyl group of carbon number 6" means not only "one hydrogen may be substituted by an alkyl group" but also "multiple hydrogens may be the same alkyl group or different Alkyl substitution". The symbols Me, Et, z-Pr and i-Bu used in the structural formula, chemical reaction formula and the like of the present specification respectively represent an anthracenyl group, an ethyl group, an isopropyl group and a tertiary butyl group. <Description of the Compound> The first invention of the present invention is a compound having a pyridyl group represented by the following formula (1). Λ

R is in the formula (1) where 'Py is a pyridyl group. This pyridyl group is specifically 2_pyrid 201229203 sigma group, 3-n ratio bite group or 4-anthracene group. Any hydrogen in the bite group may be substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a phenyl group, an anthranyl group or a 2 naphthyl group. Further, the phenyl group, the 1-naphthyl group and the 2-naphthyl group may be further substituted by an alkyl group having a carbon number or a cycloalkyl group having a carbon number of 3 to 6. R is hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or an aryl group having 6 to 14 carbon atoms. Any hydrogen in the aryl group may be substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms. Further, at least one hydrogen in the compound of the formula (1) may be substituted by deuterium.

The position of the phenyl group to which the pyridyl group is bonded in the formula (1) may be any, preferably 4 and 3, i.e., a preferred aspect of the compound of the formula (1) may be represented by the following formula (1_丨) or (12). The definitions of R and py in the formulae (M) and (1-2) are the same as those described above. Examples of the C 1 to 6 alkyl group substituted on the pyridyl group in the formula (1) are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl. , isoamyl, 2,2-dimethylpropyl, n-hexyl and isohexyl. Among the preferred alkyl groups are methyl, ethyl, isopropyl and tert-butyl, more preferred are methyl and secondary butyl. Examples of the cycloalkyl group having 3 to 6 carbon atoms are a cyclopropyl group, an anthranyl group, a cyclopentyl group, and a cyclohexyl group. The preferred cycloalkyl group is a cyclohexyl group in view of the availability of the starting material and the content of the synthesis. As for the above-mentioned exemplification, the substituents of the aryl group in which the pyridyl group is substituted, the substituent of the 2-naphthyl group, the 2-naphthyl group, and the aryl group in which r is a carbon number of 6 to 14 are also the same. The position and number of the substituents on the pyridyl group are not particularly limited. In particular, a thiol group can be substituted for any position of the acridinyl group, and the number of substitutions can be selected from 2012 to 29, 2012, and the maximum of 4 can be substituted. With regard to the alkyl group, the cycloalkyl group, the phenyl group, the 1-naphthyl group and the 2-naphthyl group which are longer than the ethyl group, it is preferable to compare the ratio of the ratio to the base ratio in consideration of the ease of obtaining the raw material or the ease of synthesis. N adjacent carbon is substituted, and the number of substitutions is preferably from 1 to 2, more preferably one. The position of R which substitutes the 1-naphthyl group in the formulae (1), (11) and 〇2) may be any, and in consideration of the ease of obtaining the raw material, it is preferably 4 and 5, more preferably 4. Examples of the C 1 to 6 alkyl group and the C 3 to 6 cycloalkyl group in R may be exemplified in the description of the substituent of the above pyridyl group. Preferred alkyl groups are methyl, ethyl, isopropyl and tert-butyl, more preferably anthracenyl and tert-butyl. A preferred cycloalkyl group is a cyclohexyl group if the availability of the starting material and the ease of synthesis are considered. The carbon number 6 to 14 aryl group in R is specifically a phenyl group, a biphenyl group, a naphthyl group or a phenanthryl group. The maximum number of substituents in the case where the functional group has a substituent is a chemically possible number, and is preferably from 1 to 3 in view of availability of the starting material and easiness of synthesis. Desirable R is a monovalent group described below.

Me Me

Me-H0— 0>- Me-0-

More preferably, the above functional groups of Me Me are as follows.

Me 0~ ΜβΗ0^-Me <Specific Example of Compound> Specific examples of the compound of the present invention are represented by the following exemplified chemical formulas. However, the present invention is not limited to the disclosure of the specific structures. <Specific Example of Compound of Formula (1-1)> Specific Example of Compound of Formula (M) The following formula (1·Μ)~(1-1-475) 11 201229203 indicates that it is preferably Formula (1-1-1)~(1-1-57), (1-1-58), (1-1-77), (1-1-96), (1-1-115), ( 1-1-134), (M-153), (1-1-172), (1-1-191), (1-1-210), and (1-1-229), and more preferably (1-1-1)~(1-1-3), (1-1-58) ' (1-1-77) ' (1-1-96) ' (1-1-115) ' (1 -1-134) > (1-1-153), (1-1-172), (1-1-191), (1-1-210), and (1-1-229).

12 201229203 t-Bu

(1-1-16)

(1-1-18)

(1-1-19)

(1-1-21)

(1-1-23)

13 201229203

14 201229203 A 1

15 201229203

16 201229203i

17 201229203

18 201229203

19 201229203

20 201229203

21 201229203

Me

(1-1-165)

Me

(1-1-167)

Me

(1-1-169)

(1-1-178)

22 201229203

Me

(1-1-192) i-Pr

(1-1-194) t-Bu

(1-1-195)

Me

(1-1-197)

Et

(1-1-198) 23 201229203

24 201229203

25 201229203

Me

26 201229203

i-Pr

27 201229203

28 201229203

29 201229203

Me

30 201229203^

31 201229203

32 201229203

33 201229203

34 201229203 α ι

(1-1-377)

(1-1-378)

(1-1-386)

(1-1-388)

(1-1-389)

35 201229203

36 201229203

Me

37 201229203

38 201229203

39 201229203

<Specific Example of Compounds of Formula (1-2)> Specific examples of the compounds of the formula (1-2) are represented by the following formulas (1-2-1) to (1-2-475), which are preferred The formula is (1-2-1)~(1-2-57), (1-2-58), (1-2-77), (1-2-96), (1-2-115) , (1-2-134), (1-2-153), (1-2-172), (1-2-191), (1-2-210), and (1-2-229), The best is the formula (1-2-1) ~ (1-2-3), (1-2-58), (1-2-77), (1-2-96), (1-2-115) ), (1-2-134), 201229203, (1-2-153), (1-2-172), (1-2-191), (1-2-210), and (1-2-229) ).

(1-2-7)~ (1-2-8) (1-2-9)

(1-2-13) 1 (1-2-14) (1-2-15)

41 201229203

42 201229203,

43 201229203

44 201229203 A 1

45 201229203

(1-2-116) 46 1 201229203

(1-2-119)

(1-2-123)

47 201229203

48 201229203

S 49 201229203

50 201229203

51 201229203

52 201229203,

(1-2-227)

(1-2-228)

(1-2-238) (1-2-239) 53 201229203

54 201229203,

55 201229203

56 201229203

57 201229203

58 201229203

(1-2-324)

(1-2-328)

59 201229203

60 201229203

(1-2-354)

61 201229203

62 201229203,

63 201229203

64 201229203

65 201229203

66 201229203.

i-Pr

t-Bu

67 201229203

68 11 201229203

<Synthesis of Compound> The synthesis method of the compound of the present invention will be described below. The compounds of the present invention can be synthesized by a suitable combination using a general and known synthesis method. The synthesis of the compound of the present invention will be described below by taking the compound (1-1-1) as an example. 2 Description 9: Synthesis of (naphthalene-1_yl) fluorene.

l) RLi or Mg or RMgX ------^ 2)(R'0)3B R'=thiol, ethyl, isopropyl, etc.

69 201229203 Reaction 2

. In the reaction 1, the ruthenium-bromonaphthalene is lithiated with an organolithium reagent, or the magnesium or organomagnesium reagent is used as a Grignard reagent to react with tridecyl borate, triethyl sulfonium borate or triisopropyl borate. And the synthesis of naphthalene boronate. Next, the succinic acid is hydrolyzed in the reaction 2 to synthesize iota naphthalene acid. Reaction 3

In Reaction 3, 1-naphthoquinone acid was synthesized by coupling 1-naphthoic acid with 9- Desert in the presence of a catalyst. Further, a method of forming a rotting acid on the onion and performing a coupling reaction may be used instead of the above-described step of forming a boric acid at the naphthalene for the coupling reaction. Reaction 4

l) RLi or Mg or RMgX 2) (R'〇) 3B R' = methyl, ethyl, isopropyl, etc.

Reaction 5

In the reaction 4, the 9-bromoindole is treated with an organic clock reagent, or the magnesium or organic reagent is used as a Grignard reagent to make it with tridecyl phthalate, oleic acid 201229203 ethyl ester or linolenic acid diisopropyl ester. The ester is reacted to synthesize 1-naphthalene side acid ester. Next, the acid vinegar was hydrolyzed in the reaction 5 to synthesize 9-oxime acid.

In Reaction 6, 9-(naphthalen-1-yl)anthracene can be synthesized by coupling 9-indoleboronic acid with bromonaphthalene in the presence of a palladium catalyst. When the naphthalene ring is coupled with the anthracene ring, it is not limited to the Suzuki coupling reaction shown in the reactions 3 and 6, and the root-shore coupling reaction or the like may be used, and the usual methods may be suitably used as appropriate. Further, commercially available products can also be used for 9-(naphthyl) anthracene. Next, a step of forming boric acid at the 1-position of 9-(naphthalen-1-yl)fluorene will be described.

In Reaction 7, the 10-position of 9-(naphthalen-1-yl)anthracene was brominated using N-bromosuccinimide. Here, a common brominating agent other than N-bromobutyric imide may also be used.

OR· 'bR' 201229203 servant, 8 + # 9养1G(naphthyl) 蒽 using organolithium reagent 妒 妒 日 日 镁 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或 或The reaction of triisopropyl sulfonate is carried out to synthesize (1〇-(naphthalene^" soil boron bismuth. Then the boronic acid ester is hydrolyzed in reaction 9, and synthesized (1〇_(naphthalene-1 group)) Bucket base) rotten acid. k, should t〇 explain m纟纟° ° (four) the synthesis of benzene.

Reaction 11

"Anal fistula or Mg or RMgX ciZn~〇 '

2) ZnCl2 ^ ZnCl2-TMEDA αζη~〇

BrO-· —

Pd-catalyst

In the reaction 10, a zinc hydride complex is synthesized from 4 唆, and then the zinc chloride complex is reacted with p-benzene in the reaction 11, and 4-(4-diphenyl phenyl) is synthesized. "ζηα2 · tmeda" in the reaction formula is a tetramethylethylenediamine complex of zinc vapor, and r in the RMgX is a linear or branched wire, and the surface is a straight ship of carbon number 4 The base or the carbon number of 3 to 4 is recorded. X is S, which can preferably make Wei, desert and moth. The coupling reaction of bismuth borate with pyridyl bromide is illustrated.

In the reaction 12, the compound (^4) of the present invention can be synthesized by combining the previous bismuth borate with π-pyridyl bromide in the presence of a catalyst. The material used in the above reaction can be appropriately modified to synthesize the present invention. Inventive 72 201229203 Other compound. For example, in the reaction 1 or 6, if an alkyl-substituted bromobenzene such as 1-bromo-4-methylnaphthalene is used instead of 1-bromonaphthalene, the synthesis can be carried out. a compound substituted with a naphthyl group. A compound in which a phenyl group is substituted with a 2- or 3-pyridyl group can be synthesized by substituting 2- or 3-iodopyridine for the 4-iodopyridine used in the reaction 10. Further, bromine can also be used. Acridine is substituted for iodopyridine. The use of m-bromoiodobenzene in place of the bromine-degrading benzene used in the reaction U can be synthesized in a compound having a π-bite group bonded to the 3-position of the phenyl group. The step of coupling iodobenzene or m-bromoiodobenzene is not limited to the above-described root-shore coupling reaction, and the eucalyptus coupling and hydrazine used in the reaction 11 can also be used depending on the kind of the raw material and the reagent which can be obtained.

It should be 8~9 in 9_(naphthalene+yl) onion 1 〇 also form micro 2 can be formed in 9_(naphthalene-1·fine Μ 而 供 供 但 但 但 但 但 但 但 但 但 但 但 但 但The reaction can be carried out, but the reaction of the product of the reaction 8 can also be carried out. Further, as shown in the above reaction 13, the hydrazine is clocked with an organolithium reagent 'either magnesium or has 4 doses with 2-isopropoxy _4. , 4,5,5-tetradecyl

Reaction 8 product of @@ directly for coupling should be read by I3, for 9 food 1G (naphthalene small) oxaborane or magnesium or organomagnesium reagent for Grenner ^ 4,4,5,5-四曱基],3,2· 73 201229203 and 'Use the catalyst and the test 9-mool-l〇_(naphthalene small) hydrazine with boronic acid pinacol ester or 4,4 as shown in Reaction 14. The 5,5-tetradecyl-1,3,2-dioxa sinter is subjected to a coupling reaction, and the same (1 〇-(naphthalen-1-yl)fluoren-9-yl) borate can be synthesized. The (1〇_(Cai Xiaoji)蒽_9_yl) benzoate thus obtained can also be suitably used for the coupling reaction of the reaction 12. Regarding the method of coupling the oxime moiety to the pyridyl phenyl bromide moiety in the final step of the synthesis, there is an example of the eucalyptus coupling reaction shown in the reaction 12, but the root-shore coupling may be used depending on the type of the raw material and the reagent available. reaction. Further, the synthesis of the compound of the present invention is not limited to the method of bringing the reaction of the oxime moiety to the terminal moiety to the final step. The pyridyl bromide substituted with an alkyl group or a cycloalkyl group bonded to an anthracene can be synthesized as shown in the following Reactions 15 to 16. Any of the alkyl or cycloalkyl-substituted pyridyl desertified benzenes can be synthesized by appropriately changing the starting materials. Reaction 1 5 ' N=< Me Reaction 16

1) RLi or Mg or RMgX 2>ZnCI2 or ZnCI2-TMEDA

Me

Media·"O-Q

The phenyl group-substituted pyridyl bromide can be synthesized as shown in the following reactions n to 18. Further, various aryl-substituted pyridyl brominated benzenes can be synthesized by appropriately changing the starting materials. Reaction 17

Br

Br<v〇 201229203 Λ 1 Reaction 1 8 CIZn-^V-/^ \=N \~~=y

Br

Pd-catalyst <reagent used for the reaction> Specific examples of the palladium catalyst used for the Suzuki coupling reaction are tetrakis(triphenylphosphine)palladium(0) : Pd(PPh3)4, bis(triphenylphosphine) Palladium dichloride pi): PdCl2 (PPh3) 2, acetic acid (II): Pd (OAc) 2, tris(dibenzylideneacetone) dipalladium (0) · Pd2 (dba) 3, three (two sub Benzylacetone) dipalladium (〇) chloroform complex: Pd2(dba)3 · CHC13, bis(dibenzylideneacetone) bis(diphenylphosphino)ferrocene]dichloropalladium(η) : pd( dppfjCl2, PdCl2[P〇Bu)2-〇NMe2-Ph)]2, etc. Further, in order to promote the reaction, a phosphine compound may be added to the palladium compounds as needed, and specific examples thereof include tris(tertiary butyl)phosphine, tricyclohexylphosphine, and 1-(N,N-dimethylamino group.曱))_2_(di-tert-butylphosphino)ferrocene, 1-(N,N-dibutylaminomethyl)_2_(di-tert-butylphosphino)ferrocene, 1-(曱Oxyfluorenyl)-2-(di-tert-butylphosphino)ferrocene, bis(di-tert-butylphosphino)-ferrocene, 2,2'-bis (di-tertiary butylphosphino, Bibinaphthalene, 2-methoxy-2'-(ditributylphosphino)-u, binaphthyl, or 2 dicyclohexyls-square-2',6'-dimethoxybiphenyl. Specific examples of the use include sodium carbonate, potassium carbonate, carbonic acid, steel, sodium oxyhydroxide, potassium hydroxide, barium hydroxide, sodium ethoxide, sodium butoxide, sodium (10), potassium phosphate or gasification. Specific examples of the agent include, stupid, toluene, xylene, hydrazine, It, methylformamide, tetrahydrofuran, diethyl ether, tert-butyl fluorenyl _, 1,4-dioxene, and Drunk 'known, ethanol, cyclopentyl methyl ether or 75 201229203 isopropyl alcohol' can be suitably selected, can be used alone or mixed The solvent is used. Specific examples of the catalyst used for the root-coupling reaction are tetrakis(triphenylphosphine). (9): Pd(PPh3)4, bis(diphenylphosphine) dichloride (η): PdCWPPh3)2 Palladium(II) acetate: Pd(OAc)2, tris(dibenzylideneacetone) IIB (0): Pd2(dba)3, tris(dibenzylideneacetone) gemini (〇) gas imitation Pd2(dba)3 · CHC13, bis(dibenzylideneacetone) (9): pd(dba)2, bis(tris-tert-butylphosphino)palladium(0), or [1,1,-double (diphenylphosphine)ferrocene] digas palladium (II): Pd(dppf)Cl2. Further, specific examples of the solvent used for the reaction include benzene, toluene, xylene 1,2,4-trimethyl phenyl, ν, fluorenyl-didecyl decylamine, tetrahydrofuran, diethyl ether butyl decyl ether, Cyclopentyl decyl ether or 1,4-dioxane. These narrowing ratios may be selected and selected, and they may be used singly or as a mixed solvent. The compound of the present invention is used for electron injection/electron transport in an organic EL device, and is applied to the field. This means that the compound of the present invention can be favorably used as an electron injecting material or electric material of an electroluminescent material. The term "electron injection layer" as used herein refers to a layer that receives electrons from the cathode to the layer 3 of the so-called electron transporting limbs. Further, the electron transport layer may also serve as an electron injection layer. Each 1: Right: The material used for Ϊτ is called an electron injecting material and an electron transporting material. Description of Organic EL Element> The present invention 2=2 is an electron injecting layer or an electron transporting layer containing: an anal element; The present invention has a low power voltage and high durability at the time of driving. The structure of the organic EL element of the present month has various aspects, basically: 76 201229203 A multilayer structure in which at least a hole transport layer is sandwiched between the anode and the cathode. The component is in the form of electric transmission, 戦f, acoustic layer, electron transport layer/cathode, (3) anode/hole injection, second layer/electrical transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode. The compound of this month has high electron injectability and thus can be compared with the elemental substance or its tilting material. The organic anal element can be used in the electron transport of the present invention: The hole injection layer, the hole transport layer, and the illuminating light are combined to scream the blue, green, red or white luminescence / the secret of the organic EL element of the present invention or the luminescent exchange 疋·〒 molecular society The edited polymer Wei (4) is listed as "Photonic Functional Materials" (co-published (1991)) The phosphorescent materials, fluorescent whitening agents, laser pigments, Qianxue Lai, various f-light analysis reagents described in P236 The luminescent material and the "organic material and display" edited by Chenge 2 (CMCBooks Publishing (2001)), the dopant materials described in P155 to 156, and the luminescent materials of the triplet materials described in P170 to 172. The compound which can be used as a light-emitting material or a light-emitting dopant is a polycyclic aromatic compound, a heteroaromatic compound, an organic metal complex, a dye, a polymer light-emitting material, a styryl derivative, an aromatic amine derivative, a coumarin derivative, a borane derivative, an oxazine derivative, a compound having a spiro ring, an oxadiazole derivative, an anthracene derivative, and the like. Examples of polycyclic aromatic compounds are anthracene derivatives, phenanthrene derivatives, condensed tetraphenyl derivatives, anthracene derivatives, chrysene derivatives, anthracene derivatives, anthracene derivatives, and erythritol derivatives 77 201229203 Examples are a pyridylquinoline derivative having a dialkylamino group or a diarylamine group, a pyridine derivative, a pyranothiophene bio-derivative, a dioxane derivative, and a triphenylamine. Base!=铍,:Organic metal complex bribe L 'money, steel, silver, turn, hungry, gold, etc. and the basis of any organism, material · continued biological, material 嗟 biological n-rays, science cut objects , turn ^ sitting ^ biological, morphine reading organisms and other complexes. The pigment _ can be a diphenyl hydride, a base derivative, (4) a derivative derivative, a di-alkylene methylene group; an oxo and a "biological, bribe, & derivative, benzo[ Benzo is a derivative such as a derivative, a benzopyrene, etc. An example of a 2-substrate luminescent material is a poly(p-phenylene)-bio-and a poly-excimer. An example of a styrene-based derivative is 4=vinyl Biological, styrene-based aromatic derivative, etc. Other electronic transmission of the organic a-component of the present invention can be used as an electron-transporting compound, an electron transport layer of an organic EL element, and an electron injection. Any of the layers of the compound is selected. Specific examples of such electron transporting materials are bismuth-based metal complexes, 2, 2' ♦ bite derivatives, morphine derivatives, biphenyl derivatives, and organisms. The secret organism "cepene derivative, tri-salt derivative" plug II = street organism, 8 · secret compound metal complex, material Lin Yan:, 啥 chewing derivative polymer, _ compound, gallium Complex, 78 201229203 * a : salivary organism, perfluorophenyl derivative, tripod derivative Products, benzoic acid derivatives, fines, hydrazine derivatives, and the like. ^The hole injecting material and the hole-transporting material used in the invention of the organic EL element can be known from the compound which has been conventionally used as a material in the photoconductive material, or the hole in the layer of the organic EL element. Choose any of the materials to use. Specific examples of such materials are a decitex derivative, a triarylamine derivative, a phthalocyanine derivative, and the like. The method of forming the film of the organic EL device of the present invention by a method such as a sputtering method, a spin coating method or a scale method is formed. Therefore, the film thickness of each layer is not __, and can be appropriately set depending on the material property f, and is usually in the range of 2 to 5 nm. As for the method of thinning the luminescent material, it is preferable to use a vapor deposition method since it is easy to obtain a core which is homogeneous and _ _ _ _ hole. The steaming conditions of the material of the present invention vary depending on the surface of the steaming head (four) (four), and it is usually preferred to set the following: The heating temperature of the boat is 50 to 40 Torr. 〇 Vacuum degree 1G.6~1().3pa, stage speed _~5〇 Leg/cle, substrate temperature is 50~+3〇〇t, film thickness is 5 to 55. . The EL element of the present invention preferably has a mechanical strength, thermal stability, and transparency in the substrate on the substrate, regardless of the structure, and a glass or a transparent plastic film can be used. The anode material may be a metal, an alloy, a conductive compound, and the (4) mixture of a work function > 4 eV, a metal such as AU, CuI, indium tin oxide (ITO), Sn02, ZnO, or the like. The cathode material may be a metal having a work function <4 eV, an alloy, a conductive person, and a mixture thereof, and specific examples are 33, @, magnesium, warp, and money alloy = slag alloy. Specific examples of the alloy are sulphuric acid, sulphuric clock, sinter/bell, town/silver, magnesium/79 201229203 indium, and the like. At least the light transmittance of the light-emitting electrode of the organic EL element is preferably 1% or more. The film thickness also depends on the sheet of the electrode material and preferably a number of μm, preferably 兮 发 Λ Λ Μ. Betong cranes range from 10 nm to 1 ® Bu. When such an electrode a# is produced, when the above electrode material is used, when the vaporization is used, the above-mentioned anode/hole injection and thin film can be described. / The light-emitting layer of the organic EL element of the electron-carrying material/cathode of the present invention = the second side of the organic EL element; the second method of forming an anode material film by vapor deposition to form an anode, and forming an electric hard layer on the electrode And the film of the hole transport layer. In = optical layer film. Vacuum on the luminescent layer _ the sub-transport of the invention == is the electron transport layer. Then, a cathode-containing material is formed by a steaming method: a substance/film is used as a cathode to obtain a target organic EL element. Further, the organic EL device may be fabricated in the reverse order, and the cathode, the electron transport layer, the light-emitting layer, the hole transport layer, the hole injection layer, and the anode may be sequentially formed. When a DC voltage is applied to the organic EL device thus obtained, the anode may be set to a + polarity, and the cathode may be a polarity, and a voltage may be applied. If a voltage of about 2 to about V is applied, the electrode may be transparent or translucent ( Luminescence was observed for the anode or cathode, and both. Further, the organic EL element emits light when an alternating voltage is applied. Further, the waveform of the applied alternating current may be any. [Examples] Hereinafter, the present invention will be described in more detail based on examples. First, a synthesis example of the compound used in the examples will be described. [Synthesis Example 1] Synthesis of Compound (1-1-1) 201229203 <Synthesis of 4-(4-bromophenyl)pyridine>

i) 'PrMgCI --» ii) ZnCI2(tmeda)

ZnCI

Br

Br~O~ 丨

Pd(PPh3)4 4-Iodopyridine 149 g and THF 689 mL were placed in a three-necked flask, and the contents were kept at a temperature of 1 ° C and 400 mL of a 2.0 Μ isopropyl magnesium sulfide THF solution was added dropwise. After completion of the dropwise addition, the mixture was stirred for 15 minutes, and 202 g of zinc chloride-tetramethylethylenediamine complex was added thereto, and the mixture was stirred at room temperature for 25 minutes. Subsequently, 226 g of p-bromoiodobenzene and tetrazolium tris(triphenylphosphine)palladium(0) 〇.34 g were added, and the mixture was heated under reflux for 3 hours. 'The reaction solution was cooled to room temperature, and an aqueous solution of ethylenediaminetetraacetic acid tetrasodium salt (730 g/1.7 L) was added to separate the organic layer. The organic layer was dried, and the desiccant was separated by filtration, and the silkworm was removed (4)* Crude product. It is called a gel tube chromatography method (expanding P-toluene to benzene/acetic acid ethyl acetate = 9/1 (volume ratio)), and the crude product is purified to obtain 4_(4_bromophenyl)pyridine 1〇2 g. <4-(4-(lG·(naphthalen-1-yl)fluorene, 9-yl) benzophene: compound (1) μ)

t-BuOH water is commercially available (10_(naphthyl) anthracene) by acid π g, Μ4· desert benzene f) guangding 4·12 g, tetrakis(triphenylphosphine) division 0.52 g, phosphoric acid Potassium 6.38 g, pseudo-lye 25 mL, second-stage ς ς τ. Gray Lu #,, - 趿丁 know 5mL, water lmL into the flask, in the nitrogen 耽 兄 brother back machine / Jtt degree disturbed 16 hour. The reaction solution was cooled to room temperature 201229203 and then washed with pure water. The solvent was removed by distillation under reduced pressure, and purified by chromatography (yield solvent: benzene to benzene/ethyl acetate = 9/1 (volume ratio)) to give 4-(4-(10_(| Small base) 蒽-9-yl)phenyl)anthracene. Set 3 9 〇 g. iH-NMR (CDC13) . δ = 8.8~8.7 (dd, 2H), 8.1 (d, 1H), 8.0 (d, lH), 7.9 (m, 2H), 7.8 (d, 2H), 7.7 (m, 4H), 7.7~76 (m, 1H), 7.6 (dd, 1H), 7.5 (m, 3H), 7.4~7.3 (m, 2H), 7.3~7 2 (m, 3H), 7.2 (m, 1H) ). [Synthesis Example 2] Synthesis of Compound (1-1-2) < 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) ) Stupid) Pyridine. Fixed synthesis>

PdCI2(dppf)-CH2CI2 KOAc

CPME will be 14.0 g of 3-(4-bromophenyl)pyridine, 18.3 g of pinacol borate, [1,1-bis(diphenylphosphino)ferrocene]digas palladium(II)-diqi 100 mL of a decane complex of 1. 5 g, potassium acetate 11.8 g, and cyclopentyl decyl ether (CPME) was placed in a flask, and stirred under a nitrogen atmosphere at reflux temperature for 4 hours. The reaction solution was cooled to room temperature, and water and toluene were added for liquid separation. The organic layer is concentrated, dissolved in toluene, and purified by activated carbon column chromatography (developing solution: toluene) to give 3-(4-(4,4,5,5-tetramethyl-1,3, 2-dioxaborom-2-yl)phenyl) octagonal (15.0 g) 〇<3·(4-(10-(qin-1-yl)-)-9-yl)benzyl)° ratio 0. Synthesis of Compound (1-1-2) >

201229203 Commercially available 9_bromo-10-(naphthalen-1-yl)anthracene 1.% g, 3_(4·(4,4,5,5-tetradecyl-1,3,2-dioxa Rotten-2-yl)phenyl)anthracene. 1.69 g, tetrakis(triphenylphosphine)palladium (0) 0.35 g, potassium phosphate 2.12 g, pseudocumene 20 mL, tertiary butanol 5 mL and water 1 mL were placed in a flask under nitrogen atmosphere at reflux temperature Stir for 16 hours. The reaction solution was cooled to room temperature, and water and benzene were added to separate the layers. The solvent was distilled off under reduced pressure. The obtained solid was purified by silica gel column chromatography (eluent: benzene/ethyl acetate). The resulting eluate is continuously passed through a column of activated carbon to remove the colored component. The solvent of the eluate was distilled off under reduced pressure, and then recrystallized with toluene to give 3-(4-(10-(naphthalen-1·yl)indole-9-yl)phenyl)acridine M8 g. 'H-NMR (CDC13): 5 = 9.1 (d, lH) > 8.7 (dd, 1H)^8.1 (mj 2H), 8.0 (d, 1H), 7.9 to 7.8 (m, 2H), 7.8 (d , 2H), 7.7 (m, 2H), '7.7 (m, 1H), 7.6 (m, 1H), 7.5 to 7.4 (m, 4H), 7.4 to 7.3 (m, 2H), 7.3 to 7.2 (m, 3H), 7.2 (m, lH). [Synthesis Example 3] Synthesis of Compound (1-1-3)

Synthesis of ίίί-IPA-water<2-(4-(1〇-(naphthalenyl-l-yl)indole_9-yl)phenyl)π-pyridinium> + commercially available (10·(naphthalene) Small base) Hui _9_ base) Boric acid 4.18 g, commercially available 2♦ bromophenyl) ° ratio of 3.37 g, tetrakis(triphenylphosphine) (〇) 0.42 g, potassium phosphate 5 〇 4 g, false Dilute 30 mL, 3 mL of isopropanol and 3 mL of water were placed in a flask and stirred under a nitrogen atmosphere at reflux temperature for 5 hours. The reaction solution was cooled to room temperature, and water and Ibenzene were added to separate the layers. The solvent was removed and the resulting solid was purified by oxidation on S column chromatography (dichlorobenzene). The solvent of the eluate was reduced and the residue was recrystallized from benzene to give 2_(4 s. naphthalene·1·yl) -9-yl) phenyl hydrazine 3 71 g. 83 201229203 ^-NMR (CDC13) : δ = 8.8 (m, 1H) > 8.3 (m, 2H) > 8 1 (d 1H), 8.0 (d, 1H), 7.9 (m, 1H), 7.9~ 7.8 (m, 3H), 7.7 to 7 6 (m 3H), 7.6 (m, 1H), 7.5 to 7.4 (m, 3H), 7.3 (m, 3H), 7.2 (m 4H). [Synthesis Example 4] Synthesis of Compound (1-M34)

<Synthesis of 9-(4-methoxyphenylH0-(naphthalen-1-yl)anthracene>

〇Me t-BuOH-water will be commercially available as 9-act-10-(naphthalene+yl)anthracene 46·〇g, (4-methoxyphenyl)picamic acid 20.1 g, tetrakis(triphenylphosphine)palladium (9)丨39 g, potassium phosphate 5〇9 g, pseudocumene 300 mL, tertiary butanol 60 mL, and water 12 mL were placed in a flask, stirred under a nitrogen atmosphere at reflux temperature for 8 hours, and then added four (triphenylene) Palladium (9) 1.39 g was stirred for 9 hours. The reaction solution was cooled to room temperature, and water was added to extract the precipitated solid matter. After drying, the crude product was dissolved in a stray and passed through a short column of toluene (toluene). , the pigment is removed from the leach solution, and 9-(4. methoxyphenyl M0-(naphthalen-1-yl)anthracene 46.5 g is obtained. < 4-(10-(^4_yl))蒽Synthesis of 9-based phenol >

NMP

Py.HCI OMe--► Word (4 methoxybenyl)_ι〇_(naphthalene_ι_yl)蒽45.2 g, σ ratio bite hydrochloric acid, Γ, ·β8 g, team methylpyrrolidone 50 mL The flask was stirred under a nitrogen atmosphere at a flow temperature for 5 hours. The reaction solution was cooled to room temperature, and water was added thereto to extract the precipitated m body. The crude product was washed with hot water, washed with decyl alcohol, and dried to obtain 42.0 g of 4 (yttrium naphthalene). 84 201229203

<Synthesis of 4,4,5,5·tetramethyl-2-(4-(10-(naphthalenyl)fluorene-9-yl)phenyl)13 2 dioxaborane>

7 94 g of 4-(10-(naphthalenyl)-indenyl-9-yl)phenyl sulfonate, 4.57 g of boronic acid benzoate, [l,i_bis(diphenyl) Phosphino)ferrocene]digas palladium-diqimethane complex 0.37 g, potassium acetate 2.67 g and cyclopentyl decyl ether (CPME) 100 mL were placed in a flask and stirred under a nitrogen atmosphere at reflux temperature. hour. The reaction solution was cooled to room temperature, and water and terpene were added to separate the layers. The organic layer was passed through a silica gel short column (developing solution: toluene), and then the eluate was concentrated, and the precipitated solid was extracted by adding Gengyuan to obtain 4,4,5,5-tetradecyl-2-(4-(10- (naphthalen-1-yl)fluoren-9-yl)phenyl)-1,3,2-dioxabenzene was degraded to 7.0 g. <2_mercapto-3-(4-(10-(4-1-yl)indolyl)phenyl)11 ratio.定: Synthesis of compound 85 201229203 (1-1-134) >

Pd(PPh3)4

K3PO4 pseudocumene-t-BuOH-water

4,4,5,5-tetradecyl-2-(4-(10-(naphthalenyl)-indolyl)phenyl)-1,3,2-dioxaline 2.02 g, 3 -Bromo-2-indenyl 0 ratio. 0.83 g, tetrakis(triphenylphosphine)palladium(0) 0.14 g, potassium phosphate 1.70 g, pseudocumene 20 mL, tertiary butanol 5 mL and water 1 mL were placed in a burning vessel under nitrogen atmosphere and reflux temperature. Mix for 5 hours. The reaction solution was cooled to room temperature, and water and benzene were added for liquid separation. The solvent was evaporated under reduced pressure, and the obtained solid was purified, m. The eluate is passed through a column of activated carbon to remove the coloring component. The solvent of the eluate was distilled off under reduced pressure, and recrystallized from toluene to give mercapto-3-(4-(1〇-(naphthalen-1-yl)indole-9-yl)phenyl). The ratio is set to 1.41 g. ^-NMRCCDC^): 5=8.6 (dd, 1H)>8.1 (d, lH)'8.0(d, 1H), 7.8 (d, 2Η), 7·8~7.7 (m, 2H), 7.7 ( m, 1H), 7.6 (m, 4H), 7.5 (m, 3H), 7.4 to 7.3 (m, 2H), 7.3 to 7.2 (m, 5H), 2.7 (s, 3H). [Synthesis Example 5] Synthesis of Compound (1-M53) <4-Methyl_3·(4-(10-(naphthalen-1-yl)fluoren-9-yl)phenyl) π Ratio σ Set Synthesis>

4,4,5,5·tetramethyl·2-(4_(1〇_(naphthalenyl)-yl-9-yl)phenyl)-1,3,2-oxo-oxo 2.02 g, 3- Desert-4-meryl group is determined to be 0.83 g, tetrakis(triphenyl 86 201229203 phosphine) (0) 0.14 g, potassium acetate 1.70 g, pseudocumene 20 mL, tertiary butanol 5 mL and 1 mL of water was placed in the flask, and the mixture was stirred under a nitrogen atmosphere at reflux temperature for 7 hours. The reaction solution was cooled to room temperature, and water and toluene were added for liquid separation. The solvent was evaporated under reduced pressure, and the obtained solid was purified by silica gel column chromatography (yield: toluene / ethyl acetate = 95/5). The eluate is passed through a column of activated carbon to remove the coloring component. The solvent of the eluate was distilled off under reduced pressure, and recrystallized from toluene to give 4-mercapto-3-(4-(10-(cain-1-yl)fluoren-9-yl)phenyl)° to a bite of 0.58. g. iH-NMR (CDC13): δ = 8.7 (m, 1H), 8.5 (m, 1H), 8.1 (d, 1H), 8.0 (d, 1H), 7.8 (m, 2Η), 7·7~7.6 ( m, 6H), 7.5 (m, 3H), 7.4 to 7.3 (m, 2H), 7.3 to 7.2 (m, 5H), 2.5 (s, 3H). [Synthesis Example 6] Synthesis of Compound (1-M72) <Synthesis of 3-mercapto-5-(4-(10-(naphthalen-1-yl)fluoren-9-yl)phenyl)β specific bite>

Me

4,4,5,5·tetradecyl-2·(4_(1〇•(naphthalenyl)蒽·9_yl)phenyl)_ 1 '3,2-oxo-roasted 2.02 g, 3->Smell-5-methyl oxime bite 0.83 g, tetrakis(triphenylphosphine), (0) 0.14 g, potassium phosphate 1.70 g, pseudocumene 20 mL, third butanol 5 mL, and water 1 The mL was placed in a flask and stirred under a nitrogen atmosphere at reflux temperature for 7 and 5 hours. The reaction solution was cooled to room temperature, and water and benzene were added for liquid separation. The solvent was evaporated under reduced pressure, and the obtained solid was purified by silica gel column chromatography (yield: toluene / ethyl acetate = 95/5). The eluate is passed through a column of activated carbon to remove the coloring component. The solvent of the eluate is distilled off under reduced pressure, and recrystallized from toluene to give 3-indole-5-(4-(1〇-(naphthalen-1-yl)indole-9-yl)phenyl) "pyridinium 1.33" g. 87 201229203 iH-NMRCCDCh) : δ=8.7 (d,1H), 8.5 (s,1H), 8.1 (d, 1H), 8.0 (d,1H), 7.9~7.8 (m,3H), 7.8 (d, 2H), 7.7 (m, 2H), 7.6 (m, 1H), 7.6 (m, 1H), 7.5 (m, 3H), 7.4 to 7.3 (m, 2H), 7.3 to 7.2 (m, 4H), 2.5 (s, 3H). [Synthesis Example 7] Synthesis of Compound (1-1-191) <2-Mercapto-5-(4-(10-(naphthalen-1-yl)fluoren-9-yl)phenyl). Synthesis of pyridine

4,4,5,5-tetradecyl-2-(4-( 10-(naphthalen-1-yl)fluoren-9-yl)phenyl)-1,3,2-dioxaborane 2.02 g, 3-bromo-6-mercaptopyridine 0.83 g, tetrakis(triphenylphosphine)i bar (0) 0.14 g, potassium phosphate 1.70 g, pseudo-ly thin 20 mL, third butanol 5 mL and water 1 mL The flask was placed in a flask and stirred under a nitrogen atmosphere at reflux temperature for 9 hours. The reaction solution was cooled to room temperature, and water and toluene were added for liquid separation. The solvent was evaporated under reduced pressure, and the obtained solid was purified by silica gel column chromatography (yield: toluene / ethyl acetate = 95/5). The eluate is passed through a column of activated carbon to remove the coloring component. The solvent of the eluate was distilled off under reduced pressure, and recrystallized from toluene to give 2-mercapto-5-(4-(10-(naphthalen-1-yl)fluoren-9-yl)phenyl group to 1.21 g. !H-NMR (CDC13) : δ = 8.9 (d, 1H), 8.1 (d, 1H), 8.0 (d, 1H), 8.0 (dd, 1H), 7.9 to 7.8 (m, 2H), 7.8 (d , 2H), 7.7 (m, 2H), 7.6 (m, 1H), 7.6 (m, 1H), 7.5 (m, 3H), 7.4~7.3 (m, 3H), 7.3~7_2 (m, 4H), 2.7 (s, 3H) [Synthesis Example 8] Synthesis of Compound (1-1-210) <2_Methyl-4-(4-(10-(naphthalen-1-yl)g-m-yl)phenyl) Synthesis of π-pyridinium > 88 201229203

4,4,5,5-tetradecyl-2-(4-(10-(naphthalen-1-yl)fluoren-9-yl)phenyl)-1,3,2-dioxaborane 2.02 g, 4-bromo-2-mercaptopyridine 0.83 g, tetrakis(triphenylphosphine)palladium(0) 0.14 g, potassium phosphate 1.70 g, pseudocumene 20 mL, third butanol 5 mL and water 1 mL The flask was placed and stirred under a nitrogen atmosphere at reflux temperature for 9 hours. The reaction solution was cooled to room temperature, and water and toluene were added for liquid separation. The solvent was evaporated under reduced pressure, and the obtained solid was purified by silica gel column chromatography (yield: toluene / ethyl acetate = 95/5). The eluate is passed through a column of activated carbon to remove the coloring component. The solvent of the eluate is distilled off under reduced pressure, and recrystallized from toluene to give 2-mercapto-4-(4-(10-(naphthalen-1-yl)indole-9(yl)phenyl)pyrene. 〇g. iH-NMR (CDC13) δ=8.ό (d,1H), 8.1 (d,1H), 8.0 (d, 1H), 7.9 (m, 2H), 7.8 (d, 2H), 7.7 (m, 2H) ), 7.7 to 7.6 (m, 1H), 7.6 (m, 2H), 7.5 (m, 4H), 7.4 to 7.3 (m, 2H), 7.3 to 7.2 (m, 4H), 2.7 (s, 3H). [Synthesis Example 9] Synthesis of Compound (1-1-229)

<3_Mercapto-4_(4-(l〇-(naphthalen-1-yl)indolyl)phenyl)pyrene synthesis>

4,4,5,5-tetradecyl-2-(4-(10-(naphthalen-1-yl)indole-9-yl)phenyl)_ 1,3,2-dioxa porch 2.02 g, 4- Desert-3-indenyl hydrazine ratio ° Hydrate 1. 〇〇e, 〇89 201229203 Tetrakis(triphenylphosphine)palladium (〇) 0.14 g, potassium phosphate 1·7〇g, false 20 mL of olefin, 5 mL of third butanol and 1 mL of water were placed in a flask, and the mixture was stirred under a nitrogen atmosphere at reflux temperature for 18 hours. The reaction solution was cooled to room temperature, and water was added and the mixture was partitioned. The solvent was distilled off under reduced pressure. The obtained solid was purified by silica gel column chromatography (eluent: benzene/ethyl acetate = 95/5). The eluate is passed through the activated carbon column to remove the coloring component. The solvent of the eluate was depressurized, and recrystallized from toluene to give 3-methyl-4(4-(1〇·(naphthalen-1-yl)fluoren-9-yl)phenyl). More than 1 g. b-NMR (CDC13): δ = 8.6 (s, 1H), 8.6 (d, 1H), 8·1 (d, 1H), 8.0 (d, 1H), 7.8 (d, 2H), 7.7 (m, 1H), 7.7 (m, 1H), 7.6 (m, 4H), 7.5 (m, 3H), 7.4 (m, 3H), 7·4 to 7.2 (m, 4H), 2.5 (s, 3H). [Synthesis Example 10] Synthesis of Compound (1_2_1) Synthesis of <4_(3-(10-(naphthalen-1-yl)fluoren-9-yl)phenyl) ° ratio &gt;

Commercially available (10-(naphthalen-1-yl)indoleyl)boronic acid 2.78 g, 4-(3-indiyl)n ratio 2.25 g, tetrakis(triphenylphosphine)palladium(9)〇·28 g 3.37 g of potassium phosphate, 20 mL of diluted, 4 mL of isopropanol and 1 mL of water were placed in a flask, and stirred under a nitrogen atmosphere at reflux temperature for 1 hour. The reaction solution was cooled to room temperature, and water and benzene were added to separate. The solvent was evaporated under reduced pressure, and the obtained solid was purified by silica gel column chromatography (eluent). The solvent of the eluate was distilled off under reduced pressure, and then crystallized from toluene to give 4-(3-(1 </RTI> <RTIgt; </RTI> <RTIgt; </RTI> <RTIgt; !H-NMR (CDC13) : δ-8.7 (dt, 2H) ^ 8.1 (d, 1H) &gt; 8.0 (d, 201229203 1H), 7.9~7.6 (m, 10H), 7.5 (m, 3H), 7.4 ~7.3 (m, 2H), 7.3~7.2 (m, ffi). [Synthesis Example 11] Synthesis of the compound (1-2-153) &lt; 4_mercapto-3-(3-(10-(naphthalen-1-yl)fluoren-9-yl)phenyl)π ratio bite synthesis>

4,4,5,5-tetradecyl-2-(3-(10-(naphthalen-1-yl)indolinyl)phenyl)-1,3,2-dioxaborane, 2.02 g, 3- Desert-4-methyl port ratio is 0.83 g, tetrakis(triphenylphosphine)palladium(0) 〇_14 g, potassium phosphate 1.7 〇g, pseudocumene 20 mL, third butanol 5 mL and 1 mL of water was placed in the flask, and the mixture was stirred under a nitrogen atmosphere at reflux temperature for 6 hours. The reaction solution was cooled to room temperature, and water and toluene were added for liquid separation. The solvent was evaporated under reduced pressure, and the obtained solid was purified by silica gel column chromatography (yield: toluene / ethyl acetate = 95/5). The eluate is passed through a column of activated carbon to remove the coloring component. The eluate was concentrated under reduced pressure, and then heptane was added to re-precipitate to give 4-(3-(10-(naphthalen-1-yl)indole-9-yl)phenyl)pyridine 1.06 g. ^-NMR (CDC13): δ = 8.6 (d, 1H) &gt; 8.5 (dd, 1H) &gt; 8.1 (d, 1H), 8.0 (dd, 1H), 7.8 (d, 2H), 7.8~7.7 ( m, 2H), 7.6 to 7.4 (m, 7H), 7.4 to 7.3 (m, 2H), 7.2 to 7.1 (m, 5H), and 2·4 (d, 3H). [Synthesis Example 12] Synthesis of Compound (1-2-172) &lt;3-Methyl-5-(3-(10-(naphthalen-1-yl)fluorene-9-yl)phenyl) 〉

201229203 4,4,5,5-Tetramethyl-2-(3-(l〇_(naphthalene~ι_yl)蒽_9-yl)phenyl)-1,3,2-dioxa shed Burning 2.02 g, 3-bromomethyl" bite 0.83 g, tetrakis(triphenylphosphine) (0) 0.14 g, potassium citrate ι·7〇g, pseudo-diluted 2〇mL, third butanol 5 1 mL of water and 1 mL of water were placed in a flask, and stirred under a nitrogen atmosphere at reflux temperature for 6 hours. The reaction solution was cooled to room temperature, and water and benzene were added to separate the layers. The solvent was evaporated under reduced pressure, and the obtained solid was purified by silica gel column chromatography (eluent: toluene/ethyl acetate = 95/5). The eluate is passed through a column of activated carbon to remove the coloring component. The eluate was concentrated under reduced pressure, and heptane was added to reprecipitate to give 3-mercapto-5-(3-(10-(naphthalenyl)pyrene)phenyl)indole i 〇1 g. h-NMR (CDC13): δ = 8.8 (d, 1H), 8.5 to 8.4 (m, 1H), 8.1 (d, 1H), 8.0 (d, 1H), 7.8 to 7.7 (m, 7H), 7.6 ( m, 2H), 7.5 (m, 3H), 7.3 (t, 2H), 7.3 to 7.2 (m, 4H), 2.4 (d, 3H). Further, the starting compound can be appropriately changed, and the other derivative compound of the present invention can be synthesized by the method based on the above synthesis example. - The following is an example of an organic EL device using the compound of the present invention, and the present invention will be described in more detail. (5), but the present invention is not limited to the examples. In the organic EL devices of the example 1 and the comparative example 1, the values of the initial voltage (V) and the initial luminance were measured in the driving test and the driving test, respectively: (m) (h).

Comparative Example of Compound Layer!, Table 2 of Electroluminescent Device of 2, 201222203 .Μ. Comparative Example 1 HI NPD Compound (A) f Compound (b) Compound (C) In Table 1, "HI" is N4,N4,cphenyl-Ν'Ν4,-bis(9-phenyl_9Η_carbazol-3-yl)·Π,ΐ'_biphenyl]_4,4'-diamine, "NPD" is Ν , hydrazine, -diphenyl-fluorene, Ν'-di-n-nyl-4,4'-diaminobiphenyl, the compound (in) is 9-phenyl-10-(4-carben-1-yl) Onion, the compound (β) is ]\^5,1\[5,1^9,]^9-7,7-hexaphenyl-7Η-benzo[C]indole-5,9-diamine, The compound (〇 is 9,1〇-bis(tetradecyridin-2-yl)naphthalen-1-yl)anthracene. The chemical structures of these compounds are shown below as well as the 8-meridene ring (Liq) used in forming the cathode.

Compound (c) [Example 1] A glass substrate (manufactured by 〇pto Science Co., Ltd.) of 26 mm x 28 mm x 〇.7 mm obtained by polishing a 180 nm thick ITO which was sputtered into a film to i5 〇 nm was used as a transparent supporting substrate. It is fixed on a commercially available vapor deposition device (the vacuum holder △ Division's substrate holder, Anshang puts HI's remanufactured ^ mining boat, puts NPD molybdenum-made evaporation boat, and puts compound (eight) molybdenum boat' 93 201229203 The steam is sold in the market, and the compound (1 small (10) steamed and 1q molybdenum vapor-deposited boat, silver-plated ginseng and ginseng into the magnesium molybdenum. The ruthenium film of the transparent support substrate is decompressed to a space of 5xl〇-4Pa, and the head υ layer is heated to the vapor deposition boat of the crucible, and the base is plated to a film thickness of 4 legs to form a hole. Inject the layer, reheat and put into the NPD vapor-deposited 1 ore to a film thickness of 25 nm to form a hole transport layer. Then add the boat of the unmanned compound (8) placed in the compound (8), : = into a light At this time, the vapor deposition rate is adjusted so that the weight of the compound __ becomes 95 and the force is 95. Next, the vapor deposition boat which is placed in the compound (i-1-i) is heated to evaporate to The electron transport layer is formed to have a thickness of μ nm. The vapor deposition rate of each layer is 〇G1 nm/see~nm/sec. Thereafter, the vapor deposition boat placed in Liq is heated to 〇〇〇3 to 〇"nm/sec. The speed is vapor-deposited until the film thickness becomes 1 nm, and the steaming boat that puts the silver and the vapor-deposited boat in which the magnesium is placed is made to have an atomic ratio of silver to magnesium of about 1:9 ^ at 0.01 to 10 nm / The vaporization speed is adjusted between sec, and the film thickness is reduced to a thickness of nm to form a cathode, and an organic EL element is obtained. If an ITO electrode is used as an anode and a Liq/magnesium-silver alloy electrode is used as a cathode, a DC voltage is applied to obtain a wavelength. A blue light emission of about 455 nm. Moreover, a constant current driving test was carried out by using a current density of 2 〇〇〇 cd/m 2 to obtain an initial luminance. The driving test starting voltage was 4 23 V, and the initial luminance was maintained. The time of the luminance of 90% or more was 71 hours. <Comparative Example 1> The compound (1-1-1) was replaced with the compound (c), and otherwise based on 94.

X X201229203 An organic EL device was obtained by the method of Example 1. The IT crucible electrode was used as an anode, and the Liq. silver alloy electrode was used as a cathode, and the current driving test was carried out by using a current density of an initial luminance of 2000 cd/m2. The driving test starting voltage was 3.73 V', and the time for maintaining the luminance of 90% or more of the initial luminance was 1 hour. The above results are summarized in Table 2. Table 2 Electron transport layer ~ Time to maintain 90% of initial luminance (hr) Starting Thunder (λΠ Example 1 Compound (1-1-1) 71 4.23 Comparative Example 1 Compound (C) 1 3.73 In addition, Production Example 2 In the organic EL device of ～12 and Comparative Examples 2 and 3, the drive start voltage (V) in the current drive test and the time to maintain the brightness of 90% or more of the initial value (h〇 measurement). DESCRIPTION OF EXAMPLES AND COMPARATIVE EXAMPLES The material constitutions of the respective layers of the produced organic EL elements of Examples 2 to 12 and Comparative Examples 2 and 3 are shown in Table 3 below.

95 201229203

_ητ Compound (D) Compound (E) Compound (F) HT Compound (D) Compound (E) Compound (G) In Table 3, "m &amp; 4 ^ ten sitting winter base Hi, 丨 ^ is, N _ two Phenyl _n4, n4' _ bis (9 phenyl phenyl)-9 9- dimethyl methine M, 4, _ diamine, HT is N_ ([1, r-biphenyl] ΐ, chemistry 9 handsome sitting winter base) phenyl)_9H 2_dongζιλ, an horse 9_(naphthyl)phenyl)-10-phenylindole, compound (E) = 4'·(4·(1 G•(naphthalene) _2·yl)蒽-9-yl)benzene

1 笑甲,二笨基·7Η•Benzo[c]苟_5,9-diyl)bis(phenylamino)) QA,--,--, and compound (&lt;3) -(4·(1〇_(naphthalenyl-1-yl)fluorenyl)) group). Bisidine.

A glass substrate (manufactured by 〇pt〇Science, Inc.) having a thickness of 180 nm and a thickness of 180 nm which was plated to a thickness of 150 nm was used as a transparent supporting substrate, and was fixed to a commercially available vapor deposition. 96 (2012) 2012 2012 2012 2012 2012 2012 2012 2012 2012 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 96 Put the compound steaming mine boat, put it into the raft, plate the boat, let the people narrate! The boat and the silver-slung seam steaming boat. 2 The following layers are sequentially formed on the IT film of the slab. Reduce the actual slot to 5x 1〇-4 Pa, Gan Jieshi is

The vapor deposition boat to the film original HI was vapor-deposited to form a hole injection layer, and then heated to a HT ▲ π: boat, and vapor-deposited to a film thickness of 30 nm to form a hole transport layer. On the other hand, the vapor deposition boat in which the compound (6) was placed and the money boat in which the compound (7) was placed were heated, and the film thickness was 35 Å to form a light-emitting layer. At this time, the steaming speed was adjusted so that the weight ratio of the object (D) to the (E) ratio was about 95:5. The two persons simultaneously heated the vapor deposition boat in which the compound (1_M) was placed and the plating boat placed in the Uq was vapor-deposited until the film thickness became 25 nm (four) into an electron transport layer. The evaporation rate is adjusted in such a way that the ratio of the substance (1 M) to the Liq t ratio is @ 1:1. The vapor deposition rate of each layer is 〇.〇〗! Nm/sec. Thereafter, the vapor-deposited boat placed in Liq is heated, and vapor-deposited at a speed of 〇.〇1 to 〇丨nm/sec until the film thickness becomes 丨nm', and the boat plate of the heating zone is placed in a silver boat. The ratio of the atomic ratio of silver to magnesium was 1:10, and the vaporization rate was adjusted at 011'10 nm/see ^ to vapor-deposit to a film thickness of (10) to form a cathode, thereby obtaining an organic EL device. A blue light having a wavelength of about 45 Å is obtained by using an ITO electrode as an anode and a [... magnesium-silver alloy electrode as a cathode to apply a DC voltage. Moreover, the strange current drive test was carried out by using the current density to obtain the initial bright p_ed/m2. _The test starting voltage is 3.89 V, maintaining the initial brightness. 97 201229203 The brightness of 90% or more is 61 hours. [Example 3] Except that the compound (1)1·1) was replaced by the compound (1-1-2), a mel element was added based on the real t. Taking the ιτ〇 electrode as the anode, _, silver &amp; gold electrode as the cathode', the current of the initial brightness of 2_ ed/m2 is used to implement the mosquito current _ test 1 city, the gorge voltage is (10)

The time at which V' maintains the luminance of the initial luminance of 90% or more is [Example 4] T An organic EL device was obtained by the method of Example 2 except that the compound (Μ-1) was replaced with the compound (ι-1-m). The current was measured by using the ιτ〇 electrode as the anode, (10), -silver, and the gold electrode as the cathode. The current was measured at a current density of 2_ ed/m2. The test (4) voltage was 3 86 V, and the time for maintaining the brightness of the initial party degree of 9 〇〇 /0 or more was 177 [Example 5] An organic EL element was obtained based on the method of Example 2 except for the compound. The constant current driving test was carried out with a Ιτ〇 electrode as an anode, (4), a silver, and a gold electrode as a cathode, with a current of 2_ ed/m2 of initial luminance. The driving test starting voltage was 3 87 V, and the time to maintain the initial brightness of 90% or more was 1 〇 1 hour. [Example 6] An organic EL device was obtained by the method of Example 2 except that the compound (1-1-1) was replaced by the compound (1-1-172). The Ιτ〇 electrode was used as the anode, and the Liq/,-silver-gold electrode was used as the cathode. The constant current driving test was carried out with a current of 2000 cd/m2. The driving test starting voltage is 3 79 98 201229203 V, and the initial brightness is maintained at 9 () for more than four (four) hours (four) hours. [Example 7] An organic EL device was known based on the method of Example 2 except that the compound (i-1-i) was replaced with the compound (M191). Taking the ιτ〇 electrode as the anode, (10) the silver, and the gold electrode as the cathode' to obtain the initial brightness 诵Q 2 current

The density was subjected to a constant f-flow drive test. Drive test start voltage is W

V, the time for maintaining the luminance of the initial luminance of 9 G% or more is 203 hours. [Example 8] T An organic I element was obtained by the method of Example 2 except that the compound (1-1-1) was replaced with the compound (1121〇). The ruthenium electrode was used as the anode, the soil Liq/mine-silver, and the gold electrode as the cathode, and the mosquito current driving test was carried out at a current density of 2000 cd/m2 at an initial luminance. The starting voltage of the occupational test is 3 58 V, and the time for maintaining the brightness of the initial luminance of 90% or more is 172 [Example 9], except that the compound (1-1-1) is replaced with the compound (1 small 229), based on the example 2 The organic EL element is obtained by the method. The IT 〇 electrode was used as the anode, and the _ cancer-silver gold electrode was used as the cathode, and the current was measured at a constant current of 2 ed/m 2 . The driving test starting voltage is I" V, and the time for maintaining the luminance of the initial luminance of 90% or more is 8 〇 small [Example 10] Except that the compound (1-1-1) is replaced with the compound (1_2_1}, based on the example 2 The organic EL device was obtained by the method. The IT 〇 electrode was used as the anode and the W magnesium-silver alloy electrode was used as the cathode, and the constant current driving test was performed at a current density of 2 〇〇〇 cd/m 2 at the initial luminance. The driving test starting voltage was 4, for example, 99 201229203 V, the time for maintaining the luminance of the initial luminance of 90% or more is 57 hours. [Example 11] Except that the compound (1-1-1) was replaced with the compound (12-153), it was obtained based on the method of Example 2. The organic EL device has a constant current driving test with an IT0 electrode as an anode and a Liq/town-silver alloy electrode as a cathode. The initial voltage of the initial brightness is 2 ed/m2. The driving test starting voltage is 3.85 V, which is maintained. The time of the luminance of the initial luminance of 90% or more was 62 hours. [Example 12] An organic EL element was obtained by the method of Example 2 except that the compound (1-M) was replaced with the compound (1-2-172). The 〇 electrode is the anode, the /, the silver, the gold electrode is the cathode' The initial luminance is called "the current density of the current density of the ^" test. The axial test voltage is 3 65 V. The time for maintaining the luminance of the initial luminance of 9 G% or more is just hour. <Comparative Example 2> In addition to the compound (1) · Μ) In addition to the compound (F), an organic EL tl piece was obtained according to the method of Example 2. The IT 〇 electrode was used as the anode, and the Liq sheng silver alloy electrode was used as the cathode 'to achieve the initial brightness _ 2 current density The test was started at a voltage of 5.35 V, and the time for maintaining the luminance of the initial luminance of 9 G% or more was 2 hours. <Comparative Example 3 &gt; In addition to the compound (1-1-1) was replaced by a compound ( In addition to G), an organic EL tl piece was obtained based on the example 2 ^ method. The ruthenium electrode was used as the anode and the u_silver j electrode was used as the cathode 'to obtain the initial luminance 2 _. (4) The initial test of the test is 4 2gv, and the time of the guarantee of 100 201229203 with an initial brightness of 90% or more is 3 hours or more. The results are summarized in Table 4. Table 4

妄 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本 本f A lighting device or the like that excites the light element. Electromechanical [Simple description of the diagram] None. [Main component symbol description] 〇*, 101

Claims (1)

201229203 VII. Patent application scope: 1. A compound' represented by the following formula (1), In the formula (1), Py is a ratio of η to a bite group, and any of the σ ratios in the β group may be a carbon group having 1 to 6 carbon atoms, a carbon group having 3 to 6 carbon atoms, and a carbon number of 1 to 6 a phenyl group substituted with an alkyl group or a cycloalkyl group having 3 to 6 carbon atoms, a 1 -Caiyl group which may be substituted with an alkyl group having 1 to 6 carbon atoms or an alkyl group having 3 to 6 carbon atoms; or a carbon number of 1 to 6 is substituted with a cycloalkyl-substituted 2-naphthyl group having 3 to 6 carbon atoms; R is hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a carbon number of 6~ Any of the hydrogens of the aryl group may be substituted by a carbon group having 1 to 6 carbon atoms or a ring having a carbon number of 3 to 6; and further, at least one hydrogen of the compound of the formula (1) Can be replaced by an atmosphere. 2. The compound according to claim 1, wherein the compound is represented by the following formula (1-1) or (1-2). In the formulae (1-1) and (1_2), Pj is a pyridyl group. Any hydrogen in the pyridyl group may be a cycloalkyl group having a carbon number of 丨6 to an alkyl group of 3 to 6 and a carbon number of 1 to 6. a 6-alkyl group or a carbon number of 3 to 6 102 201229203, a cycloalkyl-substituted phenyl group, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms, or a carbon group Substituted by a number of 1 to 6 alkyl groups or a cycloalkyl substituted 2-naphthyl group having 3 to 6 carbon atoms; R is oxygen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or carbon Any argon of the aryl group of 6 to 14 may be substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms; and, (M) or (1-2) At least one hydrogen in the compound described above may be substituted by deuterium. The compound of claim 1 or 2, wherein py is a 2-att*a group. 4. The compound of claim 1 or 2, wherein Py is 3-β thiol. 5. The compound of claim 1 or 2 wherein Py is a group. 6. The compound according to claim 1 or 2, wherein py is one selected from the group consisting of the following monovalent groups, 7. If the compound described in claim 1 or 2 of the patent scope is selected, (1'1'172)'(1-1-191)'(1-1-21〇), (; and (1) -2-172) (1-1-3), (1-1-134), (1-1-153), n〇), (1_1_229), (1-2-1) of the group of the compounds listed. ), (1-2-153) One of the groups, 103 201229203 8. An electron transporting material comprising the compound of any one of claims 1 to 7. 104 201229203^ 9. An organic electroluminescent device </ RTI> comprising: a pair of electrodes including an anode and a cathode, a light-emitting layer disposed between the pair of electrodes, disposed between the cathode and the light-emitting layer, and containing the scope of the patent application The electron transporting layer and/or the electron injecting layer of the electron transporting material according to item 8. The organic electroluminescent device according to claim 9, wherein at least one of the electron transport layer and the electron injecting layer further comprises a hydroxyquinoline metal complex and a bipyridine derivative. At least one of the group consisting of a phenanthroline derivative and a flaming derivative. The organic electroluminescent device of claim 10, wherein at least the electron transport layer and the ferrite layer are selected from the group consisting of a metal, a soil, a rare earth metal, and a base. Metals, = oxides of soil-measuring metals, _ of soil-measuring metals, halides of rare earth metals, organic morphs of metal-detecting metals, organic complexes of soil-measuring metals, and at least groups of rare earth gold Kind. The machine is in the stable and voltage application even in a film state and having high charge transportability and analogue serves as a charge transport material of an organic electroluminescent (OEL) device. By applying the electron transport material to The electron transport layer and/or the electron injecting layer of an OEL device, the lifetime of the OEL device can be logner. (1) In formula (1), Py is pyridyl, where arbitrary hydrogen may be replaced by alkyl, cycloalkyl, phenyl, 1-naphthyl or 2-naphthyl, and the phenyl, 1-naphthyl or 2-naphthyl may be substituted with alkyl or cycloalkyl R is hydrogen, alkyl, cycloalkyl or aryl, where hydrogen is hydrogenated in the aryl may be replaced by alkyl or cycloalkyl. IV. Designated representative map: (1) The representative representative of the case is: None. (2) A brief description of the symbol of the representative figure: None. 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 201229203 3 201229203 H-UO 1 jpiil is lOOl428〗 No. 4 Chinese manual no slash correction This correction date heart engine: Invention patent description (this specification format, order, do not change anything, please do not fill in the ※ part) ※Application No.: ※Application曰: Classification: 1. Invention Name: (Chinese/English) Electron transport material and organic electroluminescence device using it / ELECTRON TRANSPORT MATERIAL AND ORGANIC 〇electroluminescent device using the same II. Chinese Abstract: The present invention The compound represented by the formula (1) is characterized in that it is stable even when a voltage is applied in a thin film state and has high charge transport property, and is suitable as a charge transport material for an organic EL element. The electron transporting material is used for the electron transport %/or electron injecting layer of the organic EL element to obtain a long-life organic EL element. 〇(1) =式” is a shouting base. Any hydrogen in Guanxian can be replaced by % thiol, benzyl, 1-methyl or 2-naphthyl, phenyl, pucayl and naphthyl can be- The step is replaced by a silk or a loop wire; R rides, burns a base, a base or an aryl group. Any hydrogen in the aryl group can be substituted by a burnt group or a ring wire. Abstract: This invention provides!! 〇Λ , Ρ 0_eS a comp〇und 〇f f_ula (1 201229203 1 ^plA χ. Amendment date: March 15, 101, ΙΟΟΙ 428] No. 4 Chinese manual without scribe correction 6. Description of the invention: [Technical field of invention] The invention relates to a type of material having a material, and the use of the electron transporting material is $===the electronic wheel feeding material is simply referred to as an organic EL element, and the following is a case (hereinafter sometimes [previous technique] In recent years, the organic EL is opened Du Congda received attention, and was driven by the next-generation full-color flat panel display and the driving voltage of the component was reduced by two == practical, and a new electronic wheeling material was developed:;==== voltage reduction and long life. The patent text ^, the number record, the use of the morphine derivative or its analogue 7 = electronic material , can be low voltage compensation, piece J: the characteristics of the components reported in the example of the document (drive voltage, luminous efficiency) is only called (four) turn of the miscellaneous judgment as the real thing. In addition, 豸 2, 2 , the example of the electron transport (4) of the Lingling compound I (p_edingsQfthe i〇th International Workshop 〇n Inorganic and Organic Electr〇lUmmescence), and the patent document 2 (Japanese Patent Laid-Open No. 2〇〇2_158093) Patent Document 3 (International Publication No. 2,655, the entire disclosure of which is hereby incorporated by reference). The non-patent document 之 has a low Tg and is not practical. The compounds described in Patent Documents 2 and 3 can drive an organic EL element at a lower voltage. In order to be practical, it is expected to be more prolonged and longer. [Previous Technical Literature] 201229203 TV/UX No. 100142814 Chinese manual without scribe correction This revision date: March 15, 2010 [Patent Document] [Patent Document 1 [Patent Document 2] Japanese Patent Laid-Open Publication No. 2002-158093 [Patent Document 3] International Publication No. 2007/86552 [Non-Patent Document] [Non-Patent Document 1] Proceedin Gs of the 10th International Workshop 〇n Inorganic and Organic Electroluminescence (2000) 〇 SUMMARY OF THE INVENTION The present invention has been made in view of the problems of the prior art. In the subject of the present invention, an electron wheel t material which contributes to an extended life of an organic EL element and the like is provided. Further, an object of the present invention is to provide an organic EL element using the electron-feeding material. After intensive research by the inventors of the present invention, it has been found that a compound having a pyridyl group on a phenyl group of 9-(1-naphthyl)_1〇 or phenylene can be used in an electron two-layer of an organic EL device. Obtaining organic elements that can be driven over a long life has completed the present invention based on this finding. The above problems can be solved by the items shown below. Π] - a compound represented by the following formula (1), Γ\ R In the formula (1), py is a pyridyl group, and any hydrogen in the pyridyl group may be alkane having a carbon number of 6~6 5 201229203 ΙΟΟΙ 428] No. 4 Chinese manual No face correction This revision period: March 101 a 15 day base, a cycloalkyl group having 3 to 6 carbon atoms, a phenyl group which may be substituted with an alkyl group of carbon number 6 or a cycloalkyl group having 3 to 6 carbon atoms, an alkyl group having a carbon number of 66 or a carbon number of 3 ～6-cycloalkyl substituted 1-naphthyl' or substituted with a C 1-6 alkyl group or a cycloalkyl substituted 2-naphthyl group having 3 to 6 carbon atoms; R is hydrogen, carbon number 1~ An alkyl group of 6 or a cycloalkyl group having 3 to 6 carbon atoms or an aryl group having 6 to 14 carbon atoms. Any hydrogen in the aryl group may be an alkyl group having a carbon number of 66 or a cycloalkane having a carbon number of 3 to 6. Further, at least one hydrogen in the compound of the formula (1) may be substituted by hydrazine. [2] The compound according to [1], which is represented by the following formula (丨... or (1), RR C1'1) (1-2) In the formulae (1-1) and (1-2), Py is a pyridyl group. Any hydrogen in the pyridyl group may be an alkyl group having 1 to 6 carbon atoms and a carbon number. a ring-burning group of 3 to 6 or a phenyl group substituted with a carbon group of 1 to 6 or a cycloalkyl group having 3 to 6 carbon atoms; a group having a carbon number of 1 to 6 or a carbon number of 3 to 6; The substituted 1-naphthyl group may be substituted with an alkyl group having 1 to 6 carbon atoms or a 2-naphthyl group substituted with a carbon number of 3 to 6 ^cycloalkyl; R is hydrogen, an alkyl group having 1 to 6 carbon atoms; a cycloalkyl group having 3 to 6 carbon atoms or an aryl group having 6 to 14 carbon atoms, and any hydrogen in the aryl group may be substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms; At least one hydrogen in the compound of the formula (M) or (1-2) may be substituted by deuterium. [3] The compound according to [1] or [2], wherein py is 2-pyridyl. [4] The compound according to [1] or [2], wherein Py is 3-pyridyl. 201229203π -rv/u X is 100142814 Chinese manual without slash correction. Amendment date: March 1, 2015 [5] The compound described in [1] or [2] where Py is 4- Acridine. [6] The compound according to [1] or [2] wherein Py is one selected from the group consisting of the valent group, [7] The compound according to the above [1] or [2], which is selected from the group consisting of formula (1-1-1), (1-1-2), (M-3), (M- 134), (1-1-153), (1_M72), (1-1-191), (1-1-210), (1-1-229), (1-2-1), (1- 2-153) and (1-2-172) one of the groups of the compounds listed, 201229203 is 1001428! No. 4 Chinese manual without line correction Revision date: March 15, 1st, 1st [8] An electron-electing material, which comprises the compound according to any one of the items [5] to [7] above. [9] An organic electroluminescence device comprising: a light-emitting layer comprising an anode and a cathode interposed between the pair of electrodes, disposed in the cathode; and containing as described in the above item [8] An electron transport layer and/or an electron injection layer of the electron transport material. Sub-transfer ^ = electro-excitation element - in which the electric metal-based complex, one further contains a small to a small group of T-organisms, phenanthroline derivatives and borane derived from a group of rigid materials] In the layer and the electron injecting layer of the item [10], at least a ruthenium, an electron-emitting element, wherein the electron transporting genus, a rare earth metal, an alkali metal, and an oxide selected from an alkali metal or an alkaline earth metal, a soil test s Oxide, alkali metal halide, alkaline earth metal tooth, rare earth metal oxide, 201229203 jpiil is 100142814 Chinese manual without scribe correction. Amendment date: March, 2011, 15 曰 machine complex, alkaline earth metal There are at least one type of group. Rare earth metal halide, alkali metal organic complex and rare earth metal organic complex [Effect of the invention] The t-shaped &amp; article has a feature of high transportability even in the _ state, and is suitable as an organic EI member conveying material. The compound of the present invention can be used for an electron-transporting of an organic EL device and/or an electron-injecting layer. A long-life organic EL element can be used to produce a high-performance display device such as a full-color display. The invention is described in more detail below. In addition, in the present description, for example, "the compound represented by the formula" may be referred to as "compound (1_M)". About other chemical readings, chemical materials, domain (four) #地处理. The term "arbitrary" when defining a compound means that "not only the position but also the number can be freely selected." For example, the expression "hydrogen of (4) in the phenyl group may be substituted by the alkyl group of carbon number 6" means not only "Η@hydrogen radical substitution" but also "multiple hydrogens may be the same alkyl group or different Alkyl substitution". The symbols Me, Et, /-pr and rBu used in the structural formula, chemical reaction formula and the like of the present specification respectively represent an anthracenyl group, an ethyl group, an isopropyl group and a tertiary butyl group. &lt;Explanation of Compound&gt; The present invention is a compound having a pyridyl group represented by the following formula (1). R is in the formula (1) where 'Py is a pyridyl group. The pyridyl group is specifically 2_pyrid 201229203 1 a is 100142814 No Chinese version of the specification. Revision date: March 15, 101 pyridine, 3-pyridyl or 4-pyridyl. Any hydrogen in the pyridyl group may be substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a phenyl group, a 1-naphthyl group or a 2-naphthyl group. Further, the phenyl group, the 1-naphthyl group and the 2-naphthyl group may be further substituted by a group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms. R is hydrogen, 5 is a calcined group having 1 to 6 carbon atoms, a ring-burning group having 3 to 6 carbon atoms or an aryl group having 6 to 14 carbon atoms. Any hydrogen in the aryl group may be substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms. Further, at least one hydrogen in the compound of the formula (1) may be substituted by deuterium. The position of the phenyl group to which the pyridyl group is bonded in the formula (1) may be any, preferably 4 and 3', and the preferred form of the compound is represented by the following formula (11) or (12). Ο r\ The definitions of R and Bu in the formulas (1-1) and (1-2) are the same as those described above. Examples of the carbon number substituted on the t group in the formula (1) are methyl ethyl, n-propyl, isopropyl, n-butyl, monodecyl, isopentyl, 2,2 dimethylpropyl. Preferred examples of the base 2 are methyl, ethyl, isopropyl and tri-butyl; butyl, di: 3 and;:: group; ^ 3 to 6 examples of cycloalkyl groups are cyclopropene: J-type; A preferred cycloalkyl group is a cyclohexyl group. As for the above-mentioned example, the phenyl group, the oxime, and the ruthenium which are substituted by the occidental group are as follows: the base γ = 1 base which is changed to the filament of the carbon number 6 to U. Deliberate position: =: Can: = 10 201229203 t W Λ. For the Chinese manual of 100142814, there is no slash correction. Revision date: 1〇1 March 15曰 The maximum value that can be replaced is 4. With respect to the alkyl group, the cycloalkyl group, the phenyl group, the 1-naphthyl group and the 2-naphthyl group which are longer than the ethyl group, it is preferred to carry out the acridine group and the oxime if the availability of the starting material or the ease of synthesis is considered. Adjacent carbon is substituted, and the number of substitutions is preferably from 1 to 2, more preferably one. The position of r in which the 1-naphthyl group in the formulae (1), (Μ), and (1-2) is substituted may be any, and in consideration of the ease of obtaining the raw material, it is preferably 4 and 5, and more preferably Good is 4 people. Examples of the 厌R in the range of 1 to 6 alkyl groups and 3 to 6 carbon atoms in R are exemplified in the description of the substituents of the above-mentioned 11-bite group. Preferred leukoxyl groups are methyl, ethyl, isopropyl and tert-butyl, more preferably decyl and tert-butyl. A preferred cycloalkyl group is a cyclohexyl group if the availability of the starting material and the ease of synthesis are considered. The carbon number 6 to 14 aryl group in R is specifically a phenyl group, a biphenyl group, a naphthyl group or a phenanthryl group. When the functional group has a substituent, the maximum number of substituents is a number which is possible by learning. For example, considering the availability of the raw material and the ease of synthesis, the car is preferably 1 to 3. Preferred r is the i-valent group described below. U to Me He More preferably, the above functional groups are as follows. Me Qr Me &lt;Specific Example of Compound&gt; A specific example of the compound of the present invention is represented by the following chemical formula, but the present invention is not limited to the disclosure of the specific structure. &lt;Specific Example of Compounds of Formula (1-1)&gt; Specific Examples of Compounds of Formula (1-1) The following formula (M1)~(^ 475) 11 201229203 I Λ. Λ.Λ. Λ. Date: January 1st, March 15th, 100142814 Chinese manual, no slash correction, this is preferred, formula (1-1-1)~(1-1-57), (1-1-58) ), (1-1-77), (1-1-96), (1-1-115), (1-1-134), (1-1-153), (1-1-172), (1-1-191), (1-1-210), and (1-1-229), and more preferably, formula (1-1-1)~(1-1-3), (1-1- 58) ' (1-1-77) ' (1-1-96) &gt; (1-1-115) ' (1-1-134) ' (1-1-153), (1-1-172 ), (1-1-191), (1-1-210), and (1-1-229). 12 201229203 -T\JU X is the Chinese manual of 100142814 without a slash correction. Amendment date: March 1, 1st, 1st (1-1-19) (1-1-20) (1-1-23) (1-1-24) (1-1-27) (1-1-28) 13 201229203 ~τν_/υupu j is 100142814 Chinese manual without line correction This revision date: March 1st, 1st, 1st 14 201229203 H-VJO 1 JjJlil is the Chinese manual of 100142814 without a slash correction. Revision date: 1〇1年月月15曰 (1-1-46) (1-1-47) (1-1-48) (1-1-49) (1-1-50) (1-1-51) 〇 ❹ (1-1-61) (1-1-62) 15 201229203 For the Chinese manual of 1001428M, there is no slash correction. Revision date: 1〇1年月月15曰 16 201229203 L jpill No. 100142814 Chinese manual no underline correction date Revision date: March 1, 1 year 〇 t-Bu (1-1-87) (1-1-91) 〇 (1-1-93) (1-1-88) (1-1-96) 17 201229203 -TV/^ Α ~Ί-»ΑΧ A is 100142814 Chinese manual without line correction This revision date: 1〇1年月月15曰 (1-1-108) 18 201229203 -T\y〇 i Date of revision: March 15th, 1st, 1st, 2014 No. 100142814 Chinese manual without line correction 〇 ❹ Me Μ Me ^ (1-1-113) Me // Me (1-1-115) (1-1-117) t-Bu (1-1-119) (1-1-116) i-Pr (1-1-118) (1-1-120) % \ η Me (1-1-122) (1-1-125) \,r\/r\ // \j Me (1-1-126) (1-1-127) (1-1-129) 19 201229203 τνυ a ~^ρΐΑ a is the Chinese manual of 100M2814 without a slash correction. Revision date: 1〇1年月月15曰 20 201229203 -rv/u a Revision period: 1〇1年月15曰 is 100142814号 Chinese manual without line correction ❹ (1-1-148) Me (1-1-149) Μέ (1-1-152) (1-1-159) (1-1-160) (1-1-163) (1-1-162) t-Bu (1-1-164) 21 201229203 ~τν/υ 1 χ is 100142814 Chinese manual without line correction This revision date: March 1st, 1st, 1st Et (1-1-179) 22 201229203 ^\JO 1 jpiil is the Chinese manual for 1001428M without a slash correction. Amendment date: March 1, 1st, 1st 23 201229203 TWU A -/J-/XX X is 100142814 Chinese manual without line correction. Revision date: March 1, 1 24 201229203 ~τνυ χ is 100142814 Chinese manual without line correction This revision date: March 1 Me t-Bu (1-1-218) Me Et (1-1-216) Me (1-1-219) i-Pr (1-1-220) /) Me (1-1-221) 〇 (1-1-222) (1-1-223) (1-1-224) (1-1-225) ❹ (1-1-229) Me (1-1-230) (1-1-231) i-Pr (1-1-232) 25 201229203 Revision date: 1〇1月15月15曰100142814号 Chinese manual no underline correction t-Bu Me\_) Me' (1-1-235) Me (1-1-234) Me (1-1-236) Me’ (1-1-238) Me (1-1-239) Me^\ ir\ /r^Ui Me' (1-1-241) \J) \J Me Me (1-1-247) (1-1-244) O (1-1-248) 26 201229203 is the Chinese version of 100142814 without a slash correction. Date of revision: March 1, 1st, 1st 27 201229203 For the Chinese manual of 10&amp;42814, there is no slash correction. Amendment date: March 1, 1st, 1st 28 201229203 TV70 1 ^pxfl No. 100142814 Chinese manual without line correction This revision date: 1〇1年月月15曰 29 201229203 1 ^pil X is 100142814 Chinese manual without line correction This revision date: 1〇1年月月15曰 30 201229203n Revision date: March 15th, 1st, 1st, 10th (Tl42814 Chinese manual without line correction) 31 201229203 For the 10 〇&quot;142814 Chinese manual, there is no slash correction. Amendment date: March 1, 1st, 1st 32 201229203 τνυ x is 100142814 Chinese manual without line correction This revision date: 1〇1年月月15曰 33 201229203 -TWO JL A is 100142814 Chinese manual without line correction This revision date: March 1st, 1st, 1st 34 201229203" Revision date: March 15th, 1st, 1st, 100142814 Chinese manual, no underline correction ❹ 〇 (1-1-377) (1-1-378) 3 Γ ~j Ο (1-1-384) o c Q ^ _ _ Q Q Q (1-1-386) Me-〇 Q (1-1-387) (1-1-394) (1-1-395) 35 201229203 Revision date: March 15th, 1st, 1st, 2014 No. 100142814 Chinese manual without line correction (1-1-396) (1-1-397) Me (1-1-401) (1-1-402) i-Pr (1-1-403) t-Bu (1-1-404) (1-1-407) (1-1-408) t-Bu (1-1-411) (1-1-412) (1-1-413) (1-1-414) 36 201229203 -TV7U upifl is 100142814 Chinese manual without line correction This revision date: March 1st, 1st, 1st 37 201229203 HUOl jpiil is 100142814 Chinese manual without line correction This revision date: March 1st, 1st, 1st 〇 38 201229203 ^t\JO 1 jpifl is 100142814 Chinese manual without line correction. Revision date: March 1, 1st, 1st 39 201229203 Leaf UOl 丄 i is 100142814 Chinese manual without line correction This revision date: 1〇1年月月15曰 &lt;Specific Example of Compounds of Formula (1-2)&gt; Specific examples of the compounds of the formula (1-2) are represented by the following formulas (1-2-1) to (1-2-475), which are preferred The formula is (1-2-1)~(1-2-57), (1-2-58), (1-2-77), (1-2-96), (1-2-115) , (1-2-134), (1-2-153), (1-2-172), (1-2-191), (1-2-210), and (1-2-229), The best is the formula (1-2-1) ~ (1-2-3), (1-2-58), (1-2-77), (1-2-96), (1-2-115) ), (1-2-134), 40 201229203 , « W X. Λ X J. is No. 100142814 Chinese manual without scribe correction. Amendment date: March 15, 101 (1-2-153), (1-2-172), (1-2-191), (1-2-210), and (1-2-229). 41 201229203 Revision date: March 15th, 101. The Chinese manual of 100142814 has no underline revision. Me 42 201229203 -t\j〇upul is 100142814 Chinese manual without line correction. Amendment date: March 1st, 1st, 1st 43 201229203 HV/Oi jpill No. 100142814 Chinese manual without line correction This revision date: March 1, 1st, 1st (1-2-70) (1-2-69) (1-2-71) (1-2-72) 44 201229203 Revision date: March 15th, 1st, 1st, Chinese version of 100142814 45 201229203 Revision date: March 15th, 1st, 1st, 10th (^142814 Chinese manual without line correction) 46 201229203 For the Chinese manual of 100M2814, there is no slash correction. Revision date: March 1, 1st, 1st (1-2-117) (1-2-124) 47 201229203 Revision date: March 15th, 1st, 1st, Chinese version of 100^42814, no underline revision 48 201229203 -r\yk_» a is the Chinese version of 100142814 without a slash correction. Amendment date: March 1, 1st, 1st 49 201229203 ± Λ. Revision date: March 15th, 1st, 1st, 100142814 Chinese manual, no scribe correction 50 201229203 is the Chinese manual of 100142814 without a slash correction. Amendment date: March 1, 1st, 1st 51 201229203 is the Chinese manual of 100142814 without a slash correction (1-2-208) Me Revision date: March 1, 1st, 1st (1-2-209) Μθ (1-2-210) (1-2-211) (1-2-212) i-Pr (1-2-213) t-Bu (1-2-214) (1-2-215) (1-2-216) (1-2-217) i-Pr (1-2-218) t-Bu (1-2-219) (1-2-220) 52 201229203" For the Chinese manual of 100A142814, there is no slash correction. Amendment date: March 15, 2010 53 201229203 is the Chinese manual of 100142814 without a slash correction. Amendment date: March 1, 1st, 1st 54 201229203 is the Chinese manual of 100142814 without a slash correction. Revision date: 1〇1年年月15曰 55 201229203 ^t\ju l uyx± l is 100142814 Chinese manual without line correction This revision date: March 15, 101 56 201229203 H-UOl jplfl is 100142814 Chinese manual without line correction This revision date: 1〇1年月月15曰 57 201229203 is the Chinese manual of 100142814 without a slash correction. Amendment date: March 1, 1st, 1st (1-2-311) 58 201229203" For the Chinese manual of l〇dl42814, there is no slash correction. Amendment date: March 15, 2010 59 201229203 For the Chinese manual of l〇dl42814, there is no slash correction. Revision date: March 1st, 1st 60 201229203 -TV/U Revision date: March 15th, 1st, 1st, 100142814 Chinese manual, no underline correction ❹ 〇 (1-2-351) (1-2-356) 61 201229203 is the Chinese manual of 100142814 without a slash correction. Amendment date: March 1, 1st, 1st 62 201229203 is the Chinese manual of 100142814 without a slash correction. Revision date: 1〇1年月月15曰 63 201229203 is the Chinese manual of 100142814 without a slash correction. Revision date: 1〇1年月月15曰 64 201229203" For the Chinese manual of 100142814, there is no slash correction. Revision date: 1〇1年月月15曰 65 201229203 for the coffee 42814 _ duck _ m café w day 66 201229203 1UO丄 jpifl is 100142814 Chinese manual without a line correction. Amendment date: March 1st, 1st, 1st 67 201229203 -ruo ujJJiii is the Chinese version of 100142814 without a slash correction. Amendment date: March 1, 1st, 1st 〇 68 201229203^ τνυ 1 is the Chinese version of 100142814 without a slash correction. Amendment date: March 15, 2011 &lt;Synthesis of Compound&gt; The synthesis method of the compound of the present invention will be described below. The compounds of the present invention can be synthesized by appropriate and combined use of common and known synthetic methods. Hereinafter, the synthesis method of the compound of the present invention will be described by taking the compound (1-1-1) as an example. 2 illustrates the synthesis of 9_(naphthalene + yl) hydrazine. DRLi or Mg or RMgX 2) (R'〇) 3B R' = methyl, ethyl, isopropyl, etc. 69 201229203 &quot;Τ\_/υ 1 X Revision date: March 15, 101 For the Chinese manual of 100H2814, no line correction. Reaction 2 In reaction 1, 'pair 1-,; stinky is clocked with organolithium reagent, or with lock or organomagnesium reagent as Grignard reagent, so that it can be used with ore, triacetate or triisopropyl sulphate. Reaction, while synthesizing i•naphthalene ore gl. Then, in the anti-f should be 23, the system (4) is cut, and the 1-naphthalene is shouted. In Reaction 3, 9-(naphthalen-1-yl)anthracene is synthesized by coupling 1-naphthoic acid with 9-indole in the presence of a catalyst. Further, a method of forming a boric acid at a naphthalene and a coupling reaction at a bismuth to form a coupling reaction with a boronic acid at a naphthalene to cause a coupling reaction may be used. Or right: reverse, 4, for 9_bromofluorene lithium ionification with organolithium reagent, or magnesium &quot; magnesium reducer for Grignard reagent, make it with tridecyl borate, boric acid three 201229203 Revision date: 1〇1 On March 15th, the Chinese manual of No. 100142814 was used to synthesize the ethyl phthalate or triisopropyl borate, and the ruthenium-naphthalene borate was synthesized. Next, the boronic acid ester was hydrolyzed in the reaction 5 to synthesize 9-indole acid. Reaction 6 In Reaction 6, 9-(naphthalen-1-yl)anthracene can be synthesized by coupling 9-indoleboronic acid with 丨-bromonaphthalene in the presence of a palladium catalyst. When the naphthalene ring is coupled to the anthracene ring, it is not limited to the Suzuki coupling reaction shown in the reactions 3 and 6, and the root-side coupling reaction or the like may be used. Further, a commercially available product can also be used for 9-(naphthalen-1-yl)anthracene. Next, a step of forming boric acid at the 1-position of 9-(naphthalen-1-yl)fluorene will be described. Reaction 7 In Reaction 7, the 10-position of 9-(naphthalen-1-yl) fluorene was brominated using N-butylene diimine. Here, a conventional desertification agent other than N-bromobutyric imide may also be used. Reaction 8 71 201229203 H-UOl jpill is 100H28M Chinese manual without scribe correction. Amendment date: March 15, 2011, in reaction 8, for 9-bromo-1〇-(naphthalen-1-yl)anthracene as organolithium reagent Lithium- or magnesium or organic reagents are used as a Grignard reagent to react with tridecyl triacetate, triethyl borate or triisopropyl borate, and synthesized (1〇_(naphthalen-1-yl)蒽-9-yl) shed acrylate. Next, the boronic acid ester is hydrolyzed in the reaction 9, and (10-(naphthalen-1-yl)-he-9-yl) linonic acid is synthesized. Next, a synthesis method of pyridyl bromide benzene linked to hydrazine will be described. Reaction 10 Reaction 11 l) RLi or Mg or RMgX 2) ZnCl2 or ZnCI2.TMEDA ClZn CIZn~〇 Pd-catalyst In reaction 10, 4-iodine is used. The zinc chloride complex is synthesized by the pyridinium, and then the zinc chloride complex of § pyridine is reacted with p-bromoiodobenzene in the reaction 11, and the =(4-/odorous phenyl) bite is synthesized. "ZnCl2 · TMEDA" in the above reaction formula is a tetramethylethylenediamine complex of zinc sulfide, and RLi or Congzhong &amp; represents a linear or branched sulfhydryl group, and the bet is Wei Lin A group or a branched chain having a carbon number of 3 to 4. Χ is _ prime, it can be better to make bismuth, bromine and broken. = indicates the coupling reaction of g shoulder acid with thiol desertification benzene. 72 201229203 &quot;1-V70 1 jpifl is 100142814 Chinese manual without a slash correction. Amendment date: 1 3 1 March 15th He compound. For example, in Reaction 1 or 6, a compound having a naphthyl group substituted with an alkyl group can be synthesized by using an alkyl-substituted bromobenzene such as 1-bromo-4-methylnaphthalene instead of 1-bromonaphthalene. . The compound in which the group is substituted by a 2- or a substituent can be synthesized by substituting 2- or 3-iodopyridine for 4-iodopyridine used in the reaction 10. Moreover, bromopyridine can also be used in place of iodine. The use of m-bromoiodobenzene in place of p-bromobenzene used in the reaction U can be synthesized in a compound having a pyridyl group bonded to the 3-position of the phenyl group. The step of coupling the phenyl bromide with the pyridine bromide or the m-bromoiodobenzene is not limited to the use of the above-described root-coupling reaction, and the Suzuki coupling reaction used in the reaction 11 may be used depending on the kinds of the obtained raw materials and reagents. . Reaction 1 3 ~ In the reactions 8 to 9, boronic acid can be formed at the 10 position of the 9-(naphthalene small group) to provide a coupling reaction, but the product of the product of the reaction 8 can also be directly used for the reaction of the person. Moreover, as shown in the above reaction 13, for 9_演_1〇·(Cai Xiao^ 蒽 with _ reagent clock, or town or organic 赖 ": = quite 2: isopropoxy natetramethyl - called ^ should be P can be synthesized (10_(na-1-yl)蒽-9-yl) oleic acid. 73 201229203 'l-UO i w> pill Revision date: March 15, 2011 is 100142814 Chinese manual without scribe correction. Also, as shown in Reaction 14, using palladium catalyst and base to make 9_bromo-l〇 -(Naphthalen-1-yl)anthracene is coupled with pinacol borate or 4,4,5,5-tetramethyl-1,3,2-dioxaboran, and the same can be synthesized ( 1〇_((naphthalene_丨_yl)蒽_9_yl) boric acid vinegar. The thus obtained (1〇-(naphthalen-1-yl)indole-9()) acid vinegar can also be suitably used for the coupling reaction of the reaction 12. The final part of the synthesis is related to the 蒽. Although a method of coupling a pyridine group with a pyridine group may be given as an example of the Suzuki coupling reaction shown in the reaction 12, a root-shore coupling reaction may be used depending on the type of the raw material and the reagent to be obtained. Further, the synthesis of the compound of the present invention is not limited to the method of reacting the oxime moiety with the phenyl moiety to the final step. The π-pyridyl bromide substituted with an alkyl group or a cycloalkyl group to be bonded to an anthracene can be synthesized as shown in the following Reactions 15 to 16. It is suitable to change the raw materials to synthesize various kinds of burnt-based or cyclodextrin-substituted bite-based desertified benzene. Reaction 1 5 Me 1) RLi or Mg or RMgX --3 2) ZnCI2 or ZnCI2-TMEDA Reaction 16 ClZn-/^ Me Βγ-/~Λ-Ι ~Q. Pd_: &amp; Br-〇^ClZn Me Me The phenyl substituted pyridyl bromide can be synthesized as shown in the following Reactions 17 to 18. Further, various aryl-substituted pyridyl-bromobenzenes can be synthesized by appropriately changing the starting materials. Reaction 17 HO, Br-^VBr Br-〇-〇Hd Pd-catalyst 74 201229203 *tuoi jpifl is 100142814 Chinese manual without scribe correction This revision date: 1〇1月1515反应18 Br-〇- &gt; ClZn Pd-catalyst &lt;reagent used in the reaction&gt; Specific examples of the palladium catalyst used in the Suzuki coupling reaction are tetrakis(triphenylphosphine)palladium(0) : Pd(PPh3)4, bis(triphenyl) Palladium (II): PdCl2 (PPh3) 2, palladium (II) acetate: Pd (〇Ac) 2, tris(dibenzylideneacetone) dipalladium (0): Pd2 (dba) 3, Tris(dibenzylideneacetone)dipalladium (〇) gas-like complex: O pd2(dba)3 · CHC13, bis(diphenylideneacetone) satiety (〇): pd(dba)2, [l, l,-bis(diphenylphosphino)ferrocene]digas palladium (II): Pd(dppf)Cl2, PdCl2[P(i-Bu)2-(p-NMe2-Ph)]2 and the like. Further, in order to promote the reaction, a phosphine compound may be added to the palladium compounds as needed, and specific examples thereof include tris(tertiary butyl)phosphine, tricyclohexylphosphine, and 1-(N,N-dimethylamino group. Methyl diterpene butylphosphino)ferrocene, 1-(N,N-dibutylaminomethyl)·2_(di-tert-butylphosphino)ferrocene, 1-(methoxy Methyl)-2-(di-tert-butylphosphino)ferrocene, bis(di-trim-butyl, phosphino)ferrocene, bis(di-tris-butylphosphino-H, 1 L-binaphthyl 2-methoxy- 2'-(di-tert-butylphosphino group > u, _ binaphthyl n-yl-2,6,-dimethoxybiphenyl. Specific examples of the test used by the soil t Examples thereof include carbon_, potassium carbonate, carbonic acid chain, slave sodium, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium ethoxide, sodium butoxide, sodium acetate, potassium phosphate or potassium fluoride. Specific examples thereof include benzene, toluene, and tris(2); hydrazine, hydrazine dimethyl ketoamine, tetrahydro meth ethyl ether, 'butyl butyl amide, L methanol, ethanol, and cyclopentylmethyl group=75 201229203 is 100M2814 No. Straight line correction date of revision: March 15th, 2011, isopropyl alcohol, which is suitable It should be selected, and it can be used alone or as a mixed solvent. For the root-sequence coupling reaction; Ι ε (specific examples of the catalyst can be four (triphenyl) palladium (0): Pd (PPh3) 4, double (three Phenylphosphine)Palladium dichloride (π): PdCWPI%)2, palladium(II) acetate: Pd(OAc)2, tris(diylideneacetone), saturate (0): Pd2(dba)3, three (Dibenzylideneacetone) dipalladium (1)) chloroform complex: Pd2(dba)3 · CHC13, bis(dipyridinylacetone)! Bar (〇): pd(dba)2, double (three or three grades (0) ' or [1,1,_bis(diphenylphosphino)ferrocene]dichloropalladium(II): Pd(dppf)Cl2. Further, specific examples of the solvent used in the reaction may be mentioned. Stupid, benzene, xylene, 1,2,4-trimethylbenzene, N,N-dimethyl-methyl, tetra-n-butyl, di-butyl, secondary butyl methyl ether, cyclopentylmethyl thief 1 4_二魏. These solvents can be suitably selected as 'can be used alone or as a mixed solvent. When the electrons of the compound organic EL element towel of the present invention are injected into the 子f sub-transport layer', it is stable when an electric field is applied. The wire of the present invention can be used well as an electronic injection material for electroluminescent materials. The term "electron injection layer" as used herein refers to a layer of "layer", the layer of the layer "the layer of the electron transport layer refers to the layer of electricity", and the layer of the electron transport layer can also serve as an electron injection layer EL. Low driving voltage of the element and durability at the time of driving. The organic EL element of the present invention has various structures, basically 76. 201229203 Revision date: March 15, 101 The line correction is based on the multi-sound (four) of the layer sandwiched between the anode and the cathode. - Examples of concrete structures from the hole-bearing layer, the first layer, and the electron wheel a θ '° are (1) anode/electric=/electric reading cathode, (1)_first layer/electron transport layer/ramp (3) Anode/electron injection b 2 5 tree layer / luminescent layer / electron transport layer / electron injection layer / cathode, and the like. The compound has high affinity and electron transportability, and can be used for the electric layer in combination with a single substance or other materials. The invention has the 嫱m _ from the electric ding / the 嘈 嘈 书 输 # # #: : 5 pieces of light can be obtained by adding a =tr injection layer, a hole transport layer 'light emitting layer, etc. to the electron transporting material of the present invention to obtain blue, green, red or white light. The luminescent material or the luminescent material of the polymer functional material series ""White 1991)), which is described in P236, is a luminescent material, a substance, a body, a technical analysis reagent, a luminescent material. 'And the editor-in-chief of the City 2, etc. (a ks publication (fine: ΡΠ (ΡΠ Μ 记载 记载 记载 记载 记载 记载 记载 记载 记载 记载 记载 记载 记载 记载 记载 记载 记载 Μ Μ Μ Μ Μ Μ Μ Μ Μ Μ Μ Μ Μ Μ Μ Μ 。 。 。 。 四 四 四Group compounds, organometallic complexes, pigments, fluorene-based luminescent materials, styryl derivatives, aromatic amine derivatives, scent derivatives, occupational derivatives, t-qin derivatives, compounds having a spiro ring , 嗓二精生物,骑生物#. Examples of multi-faceted compounds 蒽 derivatives, phenanthrene derivatives, thick tetraphenyl derivatives, ke derivatives (Chry_) derivatives, garden derivatives, lotus derivatives, red labor derivatives 77 201229203 HUO 1 jpil 1 is the Chinese version of 100142814 without a slash correction. The date of this amendment: March 15, 101. Examples of heteroaromatic compounds are oxadiazole derivatives with dialkylamino or diarylamine groups, pyrazoles. a quinoline derivative, a pyridine derivative, a pyran derivative, a phenanthroline derivative, a fluorene heterocyclic pentadiene derivative, a triphenylamine group, a phenanthene derivative, a quinacridone derivative, etc. Examples of the substance are zinc, Ming, Ιέ, 铕, bin, 镝, 铱, 翻, iron, gold, etc. with a porphyrin derivative, a benzoxazole derivative, a benzothiazole derivative, an oxadiazole derivative. a complex of a thiadiazole derivative, a benzimidazole derivative, a pyrrole derivative, a pyridine derivative, a phenanthroline derivative, etc. Examples of the pigment may be a compound, a polydecyl derivative, a foreign Derivatives, fragrant derivatives: dicyanomethylene-pyran derivatives a pigment such as a cyano-f-methylpyran derivative, a f-substituted benzopyrene derivative, an sigh-derivative, a flower derivative, a benzocentric derivative, a benzothiazole derivative, or a benzimidazole derivative. Examples of the molecular light-emitting material are a poly-p-styrene derivative, a polyphenanthene derivative, a polyethylene-containing organism, a poly-wei derivative, a (tetra) derivative, a benzene: a living, etc. An example of a styrene derivative is An anthracene-containing bio-organic, distyryl-based aromatic derivative, etc. Other electron-transporting materials used in the organic EL device of the invention can be used as an electron-transporting compound from 〇-DU, Zengdian materials, and can be used in organic EL.兀^ The electron transport layer and the electron injecting layer compound are arbitrarily selected. The specific example of the material to be sent is the metal mismatch from σ疋彳叮 biological, phenanthroline derivative, biphenyl hydrazine derivative, 茈=(4) a metal complex of a derivative of a substance, an sigh, a trisamine, a polymer of a radionuclide, a steroid, a gallium complex, 78 201229203 ^fU5I3pifl is a circle 428 Chinese manual without line correction this correction date :1〇1年月]5曰(4) derivatives, perfluoro stupid base, benzoquinoline derivatives, imidazolium, pyrazine derived organic a-member of the invention; Creatures, etc. The material can be used for photoconductivity from the previous ones; the compound m _ for the material to be sent as the material of the hole =: r material, == Ο structure ^ 2 organisms, diamine derivatives, 駄Cyanine derivatives and the like. Each layer of the organic EL element can be formed by vapor deposition (four) a material constituting the film. For example, if you want to use it, you can use it according to the material's suitability. From the perspective of easy-to-use and pinholes, it is better to use S3. Preferably, it is suitably set in the following range: boat plus ',,,,, 50 40 〇 C, vacuum degree 〜 6 〜 l 〇 -3 Pa, steaming speed 0.01-50 Ο mail / coffee, substrate temperature is seven G ~ +3() (rc, film thickness is $譲~5 division. The organic EL reading of the present invention is preferably implanted on the substrate regardless of the above structure. The substrate has mechanical strength, thermal stability and transparency. A glass, a transparent plastic film, etc. can be used. The anode material can be a work function &gt; 4, a metal, an alloy, a conductive compound, and a mixture thereof, and specific examples are metals such as u, Cul, indium tin oxide (IT〇), Sn〇 2. Zn〇, etc. The cathode material may be a mixture of metals, alloys, and conductive compounds having a work function &lt; 4 eV, and specific examples are aluminum, calcium, magnesium, lith, magnesium alloys, aluminum alloys, etc. Specific examples of the alloy are Aluminum / lithium fluoride, aluminum / lithium, magnesium / silver, magnesium / 79 201229203 ^UOl^pni Revision date: 101 years 3 In the Chinese manual of No. 1001428M on the 15th of the month, there is no scribe line correction. In order to make the emission efficiency of the organic EL element excellent, it is preferable that at least the light transmittance of the electrode is 1 G% or more. Hundreds of Ω / port or less. The film thickness also depends on the nature of the electrode material, usually excitation ~ ^ μπι, preferably in the range of 10 ~ 400nm. When making such an electrode, using the above electrode material, evaporation or still Forming a thin film. Next, a method for producing an organic EL element including an anode/hole injection layer/hole transport layer/light-emitting layer Benmuming electron transport material/cathode; and an organic EL element for using the light-emitting material of the present invention The method of forming a thin film of an anode material on a substrate by vapor deposition to form an anode, a film of a hole injection layer and a hole transport layer, and vacuum evaporation of the electron beam on the light-emitting layer The private test method forms a cathode film containing a cathode as a cathode to obtain a target organic EL device. Further, the organic EL device is fabricated in the reverse order, and the steps are sequentially formed: an electron transport layer, a light-emitting layer, and electricity. When the DC voltage is applied to the organic EL element thus obtained, the voltage is applied to the ten-polarity and the cathode is set to _ polarity, and the voltage can be applied as long as the voltage is applied to the voltage of 2 to ^ right. Or semi-transparent electrode side (anode or cathode, St to illuminate. And 'the organic' piece can apply any alternating current, the waveform of the applied current can be any. The following is a more detailed description of the invention based on an example. Synthesis example of the compound to be used. [Synthesis Example 1] Synthesis of compound (ι-m) ι Ω 201229203 Revision date: March 15, 2011, 100142814 No Chinese text specification, no slash correction, &lt; 4-(4- &gt;Synthesis of the base of the odor base&gt; 丨)丨PrMgCI ii) ZnCl2(tmeda) ^ ^~ZnCI -ZnCI N Ο ο Put 4-light bite 149 g and ΤΗρ 689虮 into the three contents and keep the temperature at rc. One bottle will be .v?^ 4ΠΠ τ, mouth · Μ isopropyl magnesium chloride thf f, add end After 15 minutes, the lion's ethylenediamine complex 202g, uterine, milk, T, T, T, benzene, g, and tetra (triphenylphosphine ςζ ° ° force _ the reaction solution was cooled to room temperature, heated to reflux for 3 hours. Γ7λ 〇α/17Τ^ '』,, and an aqueous solution of tetraammonium tetraacetate (730 g/l.7L) is added to the organic layer to separate the desiccant, and the mixture is removed under reduced pressure. After the over/under knife, the crude product is purified, and (4) stupid base ^ (prepared by r base into a bucket base) phenyl) shout: compound (Μ-D combination) Commercially available (10-(naphthalene sulphate) _9_yl) yue 5 22 g, 4 puprophenyl ί ^ 4 · 12 g, tetrakis(triphenylphosphine) G · 52 g, potassium silicate 6.38 g, 25 l of secondary production, 5 mL of secondary butanol, and 1 mL of water were placed in a flask at a nitrogen gas reflux temperature for _ 16 hours. Cooling the reaction solution to room temperature 81 201229203 HUOl JjJUl is 100M2814 Chinese manual without scribe correction. Date of revision: After March 15th, 1st, it is washed with pure water. The solvent was distilled off under reduced pressure, and purified by silica gel chromatography (yield solvent: benzene benzene to benzene/ethyl acetate = 9/1 (volume ratio)) to give 4-(4-(10-(naphthalene-1). -Based) 蒽) phenyl) 0 is pyridine wo g. h-NMR (CDC13): δ=8.8~8.7 (dd, 2H), 8.1 (d, 1H), 8·° (d, 1H) ' 7.9 (m, 2H) &gt; 7.8 (d, 2H) &gt; 7.7 (m, 4H) &gt; 7.7-7.6 1H)^7.6 (dd, 1H)'7.5 (m, 3H)&gt; 7.4-7.3 (m, 2H)'7.3-7.2 (m, 3H), 7.2 (m , 1H). [Synthesis Example 2] Synthesis of Compound (1-1-2) (4-(4,4,5,5-tetradecyl-1,3,2-dioxanthene-2-yl)phenyl) Selected composition &gt; 〇 PdCI2(dppf)_CH2CI2 KOAc CPME 3-(4-bromophenyl)pyridine Ho g, boronic acid pinacol ester 18·3 g, U'U bis(diphenylphosphino)ferrocene]dichloropalladium (π)_diqi methane The complex i'5 §, potassium acetate 11.8 g, and cyclopentyl decyl ether (CPME) 100 mL were placed in a vial and stirred under a nitrogen atmosphere at reflux temperature for 4 hours. The reaction solution = but at room temperature was added with water and benzene was used for liquid separation. The organic layer was concentrated and dissolved in toluene'. Purified by activated carbon column chromatography (developing liquid: toluene) to obtain 3_(4_(4,4, tetramethyl-1,3,2-dioxane shed _ 2-yl)phenyl)anthracene. Set (no g). &lt;3~(Φ·(1〇·(naphthalen-1-yl)furanyl)phenyl)pyromycin: Synthesis of Compound (112): &gt; 4 82 201229203 M-UOl jpill One is the Chinese manual of 1001428M No underline correction This revision date: 9-bromo-10-(naphthalen-1-yl)fluorene 1.96 g, 3 will be commercially available on March 15, 1st, 1st -(4-(4,4,5,5-tetradecyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine 1.69 g, tetrakis(triphenylphosphine)palladium (0 0.35 g, potassium phosphate 2.12 g, pseudocumene 20 mL, tertiary butanol 5 mL, and water 1 mL were placed in a flask, and the mixture was purged under a nitrogen atmosphere at reflux temperature for 16 hours. The reaction solution was cooled to room temperature, and water and benzene were added to separate the layers. The solvent was distilled off under reduced pressure. The obtained solid was purified by silica gel column chromatography (eluent: toluene/acetic acid acetonitrile 9/1). The resulting eluate is continuously passed through a short tube of activated carbon to remove the colored component. The solvent of the eluate was distilled off under reduced pressure, and then recrystallized from toluene to give 3-(4-(1)-(naphthalen-1-yl)indole-9-yl)phenyl)acridine 1.48 g 1H-NMR ( CDC13): 5 = 9.1 (d, lH) '8.7 (dd, 1H) &gt; 8.1 2H), 8.0 (d, 1H), 7.9~7.8 (m, 2H), 7.8 (d, 2H), 7·7 (m, 2H), 7.7 (m, 1H), 7.6 (m, 1H), 7.5 to 7.4 (m, 4H), 7.4 to 7.3 (m, 2H), 7.3 to 7.2 (m, 3H), 7.2 (m , 1H). [Synthesis Example 3] Synthesis of Compound (M-3) Commercially available (1〇-(naphthalen-1-yl)fluoren-9-yl) linonic acid 4.18 g, commercially available 2-(4-phenylene)pyridine 3.37 g, tetrakis(triphenylphosphine)palladium (0) 0.42 g, potassium phosphate 5 〇 4 g, pseudo cumene 30 mL, isopropanol 3 mL, and water 3 mL were placed in a flask, and stirred under a nitrogen atmosphere at reflux temperature for 5 hours. The reaction solution was cooled to room temperature, and water and benzene were added to separate the layers. The solvent was evaporated under reduced pressure, and the obtained solid was purified by silica gel column chromatography. The solvent of the eluate was distilled off under reduced pressure, and recrystallized from toluene to give 2-(4-(10-naphthyl)indole-9-yl)phenyl)n-pyridinium 3 71 g. 83 201229203 For the Chinese manual No. 100!42814, the W-NMR (CDC13) is not underlined: δ=8.8 (m, 1H), 8.3 (m, 2H), 8.1 (d 1H), 8.0 (d, 1H)' 7.9 (m, 1H), 7.9 to 7.8 (m, 3H), 7.7 to 7.6 (m, 3H), 7.6 (m, 1H), 7.5 to 7.4 (m, 3H), 7.3 (m, 3H), 7.2 ( m, 4H). [Synthesis Example 4] Synthesis of Compound (1-1-134) &lt;Synthesis of 9-(4-methoxyphenyl)_10_(naphthalene·n)蒽 Pseudo-cumene-t-BuOH-water will be commercially available as 9-bromo-10·(naphthalen-1-yl)anthracene 46.0 g, (4-methoxyphenyl)boronic acid 20.1 g, tetrakis(triphenylphosphine) (〇)1 39 g, potassium phosphate 5〇9笆, pseudocumene 300 mL, tertiary butanol 6〇mL and water 12 mL were placed in the flask, and mixed under nitrogen gas at reflux temperature for 8 hours. Additional tetrakis(triphenylphosphine)-saturated (9) 139 g was added for 9 hours. The reaction solution was cooled to room temperature, and water was added to extract a precipitated solid. After drying, the crude product is dissolved in toluene and passed through a gel column (developing solution: toluene) to distill off the solvent of the eluate to obtain 9-(4-methoxyphenyl)-10-(naphthalene). -1-yl)S 46.5 g. &lt;Synthesis of 4-(1〇-(naphthyl)fluorene-9-yl) phenol;&gt; Put 9_(4)methoxyphenyl)-10-(naphthalen-1-yl)indole 4S.2 g, bite-acid 'methylpyrrolidone 50 mL into the flask under nitrogen ', =^ _ 5 hours . The reaction solution was cooled to room temperature, and water was added to a solid. The crude product was washed with hot water, washed with methanol, and then dried to give 4-(1?-(naphthalenyl) phenanthyl)phenol 42.0 g. 84 201229203 *tuo i ^pifl is the Chinese manual of 1001428H without a slash correction. The revised period: March 15, 101 G.37 g of hydrazine gas, G.37 g of acetic acid, and 2.67 g of (0.5E) acetic acid were placed in a flask. The mixture was stirred for 4 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature, water and ς ^ organic layer was passed through a short column of Shixia plastic (expansion liquid: sputum), the dissolution knife was centrifuged, and heptane was added to extract the precipitated solid to obtain 4 ' &lt; 2-methyl moiety _(10_(naphthalene+yl)蒽_9_yl)phenyl)^定:化|物85 201229203 HUOl-Jpill 100142814号 Chinese manual no underline correction This revision date is March 15th Synthesis of (1-1-134) &gt; 4,4,5,5-tetramethyl-2-(4-(10-(naphthalen-1-yl)fluoren-9-yl)phenyl)-1,3,2-dioxaborane 2.02 g, 3-bromo-2-methylpyridine 0.83 g, tetrakis(triphenylphosphine)palladium(0) 0.14 g, potassium phosphate 1.70 g, pseudocumene 20 mL, tertiary butanol 5 mL, and water 1 mL The flask was placed in a flask and stirred for 5 hours under a nitrogen atmosphere at reflux temperature. The reaction solution was cooled to room temperature, and water and toluene were added for liquid separation. The solvent was evaporated under reduced pressure, and the obtained solid was purified by silica gel column chromatography (yield: benzene/ethyl acetate = 95/5). The eluate is passed through a column of activated carbon to remove the coloring component. The solvent of the eluate was depressurized and recrystallized from toluene to give 2-methyl-3-(4-(10-(naphthalen-1-yl)indole-9-yl)phenyl)pyridine M1 g. ^-NMR (CDC13): 5 = 8.6 (dd, 1H) '8.1 (d, 1H)' 8.0 (d, 1H), 7.8 (d, 2H), 7.8 to 7.7 (m, 2H), 7.7 (m, 1H), 7.6 (m, 4H), 7.5 (m, 3H), 7.4 to 7.3 (m, 2H), 7.3 to 7.2 (m, 5H), 2.7 (s, 3H). [Synthesis Example 5] Synthesis of compound (1-1-153) &lt; 4-mercapto-3-(4-(10-(naphthalen-1-yl)fluoren-9-yl)phenyl) σ ratio Synthesis > Me B-^· Pd(PPh3)4 K3P〇4 pseudocumene-t-Bu〇H-water 4,4,5,5-tetramethyl-2-(4-(10-(tea-1-yl) En-9-yl)phenyl)-1,3,2·dioxaborane 2.02 g, 3-bromo-4-indolylpyridinium·83 g, tetrakis(triphenyl 86) 201229203 τν/u X f Fl is 100H2814 Chinese manual no underline correction This revision date: March 15, 101 phosphine) (9) 0.14 g, potassium phosphate 1.70 g, pseudo cumene 20 mL, tertiary butanol 5 mL and water 1 mL The flask was placed in a flask and stirred under a nitrogen atmosphere at reflux temperature for 7 hours. The reaction solution was cooled to room temperature, and water and toluene were added for liquid separation. The solvent was evaporated under reduced pressure, and the obtained solid was purified, m. The eluate is passed through a column of activated carbon to remove the coloring component. The solvent of the eluate was distilled off under reduced pressure, and then recrystallized from toluene to give 4-ytyl-3-(4-(10-(naphthalen-1-yl)indole)phenyl)π-pyridinium 58 g. 0 lH_NMR(CDC13): S = 8.7 (m, 1H), 8.5 (m, 1H), 8.1 (d, 1H), 8.0 (d, 1H), 7.8 (m, 2H), 7.7~7.6 (m, 6Η) ), 7·5 (m, 3H), 7.4 to 7.3 (m, 2H), 7.3 to 7.2 (m, 5H), 2.5 (s, 3H). [Synthesis Example 6] Synthesis of Compound (1-1-172) &lt; Synthesis of 3-mercapto-5-(4-(10-(naphthalen-1-yl)indole-9)ylphenylpyridinium &gt; 44,4,5,5-tetramethyl-2-(4-(1〇-(naphthalen-1-yl)indolyl)phenyl)_ 1,3,2-dioxaborane 2.02 g, 3-bromo-5-mercaptopyridine 0.83 g, tetrakis(triphenylphosphine) Put (0) 0.14 g, potassium phosphate 1.70 g, pseudocumene 2 site, third butanol 5 mL and water 1 mL The flask was stirred under a nitrogen atmosphere at reflux temperature for 7.5 hours. The reaction solution was cooled to room temperature, and water and toluene were added for liquid separation. The solvent was distilled off, and the obtained solid was purified by silica gel column chromatography (eluent: EtOAc/ethyl acetate = 95/5). The eluate is passed through a column of activated carbon to remove the coloring component. The solvent of the eluate was distilled off under reduced pressure, and then toluene was recrystallized to give 3-methyl-5-(4-(10-(naphthalene+yl)) phenyl) phenyl). 87 201229203 HVJO 1 丄 is 100142814 Chinese manual without slash correction This revision date: 1〇1年月月15臼'H-NMR (CDC13) : 6=8.7 (d, 1H) ' 8.5 (s, 1H) ' 8.1 (d, 1H), 8.0 (d, 1H), 7.9 to 7.8 (m, 3H), 7.8 (d, 2H), 7.7 (m, 2H), 7.6 (m, 1H), 7.6 (m, 1H) , 7.5 (m, 3H), 7.4 to 7.3 (m, 2H), 7.3 to 7.2 (m, 4H), 2.5 (s, 3H). [Synthesis Example 7] Synthesis of Compound (M-191) &lt;2_Methyl-5-(4-(l〇-(naphthalen-1-yl)fluoren-9-yl)phenyl) π) 〉 Cr^ Pd(PPh3)4 ~ K3P〇4 pseudocumene-t-Bu〇H-water 4,4,5,5-tetradecyl-2_(4_(10_(naphthalene small))蒽_9_ Base) phenyl), 1,3,2-&gt;-oxo-degraded 2.02 g, 3-&gt; odor-6-mercapto-α ratio bite 0.83 g, tetrakis(triphenylphosphine)palladium(0) 0 .H g, potassium phosphate 1_7〇g, pseudocumene 20 mL, third butanol 5 mL, and water 1 mL were placed in a flask, and stirred under a nitrogen atmosphere at reflux temperature for 9 hours. The reaction solution was cooled to room temperature, and water and toluene were added for liquid separation. The solvent was evaporated under reduced pressure, and the obtained solid was purified by silica gel column chromatography (yield: toluene / ethyl acetate = 95/5). The eluate was passed through a short tube of activated carbon to remove the coloring component. The solvent of the eluate is distilled off under reduced pressure, and recrystallized to give 2-methyl-5-(4-(10-(naphthalen-1-yl)indole-9-yl)phenyl)»» 1.21 g. iH-NMR (CDC13): δ = 8.9 (d, 1H), 8.1 (d, 1H), 8.0 (d 1H), 8.0 (dd, 1H), 7.9 to 7.8 (m, 2H), 7.8 (d, 2H) ), 7.7 2H), 7.6 (m, 1H), 7.6 (m, 1H), 7.5 (m, 3H), 7.4 to 7.3 (m 3H), 7·3 to 7.2 (m, 4H), 2.7 (s, 3H). [Synthesis Example 8] Synthesis of Compound (M-210) &lt;Synthesis of 2-(indolyl-4-(4-(1〇-(naphthalen-1-yl)g, _9-yl)phenyl)indole&gt; 88 201229203 ^\JO 1 JJJifl is the Chinese manual of 100M2814 without a slash correction. Amendment date: March 15, 101 44,4,5,5-tetramethyl-2-(4-(10-(cain-1-yl)en-9-yl)phenyl)_ 1,3,2-dioxaborane 2.02 g, 4-bromo-2-mercaptopyridine 0.83 g, tetrakis(triphenylphosphine)palladium(0) 0.14 g, potassium phosphate 1.70 g, pseudocumene 20 mL, third butanol 5 mL, and water 1 mL The flask was placed and stirred under a nitrogen atmosphere at reflux temperature for 9 hours. The reaction solution was cooled to room temperature, and water and toluene were added for liquid separation. The solvent was evaporated under reduced pressure, and the obtained solid was purified by silica gel column chromatography (yield: EtOAc/EtOAc). The eluate is passed through a column of activated carbon to remove the coloring component. The solvent of the eluate was distilled off under reduced pressure, and recrystallized from toluene to give 2-indole-4-(4-(1〇-(naphthalen-1-yl)fluoren-9-yl)phenyl)pyridine 1.2〇. g. ^-NMR (CDC13) δ = 8.6 (d, 1H) ' 8.1 (d, 1H) &gt; g.〇(d, 1H), 7.9 (m, 2H), 7.8 (d, 2H), 7·7 ( m, 2H), 7.7~7.6 (m, 1H), 7.6 (m, 2H), 7.5 (m, 4H), 7.4~7.3 (m, 2H), 7.3~7, 2 (m: 4H), 2.7 ( s, 3H). 'Synthesis Example 9> Synthesis of Compound (1-1-229) &lt; Synthesis of 3-mercapto-4-(4-(10-(naphthalen-1-yl)fluoren-9-yl)phenylpyridinium &gt; 4,4,5,5-tetradecyl-2-(4-(10-(naphthalen-1-yl)1-9-yl)phenyl)-1,3,2-dioxaborane 2.02 g, 4-bromo-3-mercaptopyridine hydrochloride 1〇〇Ο 89 201229203 woi jpni is l〇〇l42814 Chinese manual without line correction This revision date: 1〇1年月15日四(三笨Palladium (0) 0.14 g, potassium phosphate 1.70 g, pseudocumene 20 mL, third butanol 5 mL, and water 1 mL were placed in a flask, and stirred under a nitrogen atmosphere at reflux temperature for 18 hours. The reaction solution was cooled to room temperature, and water was added and the mixture was partitioned. The solvent was evaporated under reduced pressure, and the obtained solid was purified m. The eluate was passed through a column of activated carbon to remove the coloring component. The solvent of the eluate was distilled off under reduced pressure, and the crystal was recrystallized to give 3-methyl-4-(4-(10-(naphthalen-1-yl)®-9-yl)phenyl) π ratio σ1. 2 g. 'H-NMR (CDC13): 6=8.6 (s, 1H) &gt; 8.6 (d, 1H) &gt; 8.1 (dj 1H), 8.0 (d, 1H), 7.8 (d, 2H), 7.7 (m, 1H), 7.7 (m, 1H), '7.6 (m, 4H), 7.5 (m, 3H), 7.4 (m, 3H), 7.4 to 7.2 (m, 4H), 2.5 (s, 3H). [Synthesis Example 10] Synthesis of Compound (1-2-1) &lt;Synthesis of 4-(3-(1〇•(naphthalen-1-yl)indole_9-yl)phenyl)π-pyridinium> Commercially available (10-(naphthalen-1-yl)indole-9-yl)boronic acid 2,78 g, 4-(3-bromophenyl) ° ratio of 2.25 g, tetrakis(diphenylphosphine)| Ba (〇) 〇 28 g, potassium silicate acid 3.39 g, pseudo cumene 20 mL, isopropanol 4 mL, and water 1 mL were placed in a flask, and stirred under a nitrogen atmosphere at reflux temperature for 1 hr. The reaction solution was cooled to room temperature, and water and benzene were added to separate. The solvent was evaporated under reduced pressure, and the obtained solid was purified by silica gel column chromatography. The solvent of the eluate was distilled off under reduced pressure, and then recrystallized from toluene to give 4-(3-(1 〇-(naphthalenyl) hydrazine) phenyl wind bite (i 54 g). H-NMR (CDC13) : δ =8·7 (dt, 2H), 8.1 (d, 1H), 8.0 (d, 90 201229203 Amendment date: March 1st, 1st, March 15th, 100142814 Chinese manual, no slash correction, 1), 7·9 ～7.6 (m, 10H), 7.5 (m, 3Η), 7·4 to 7.3 (m, 2Η), 7·3 to 7.2 (m, 4Η). [Synthesis Example 11] Compound (1-2-153) Synthesis of &lt;4-mercapto-3-(3-(10-(naphthalen-1-yl)fluoren-9-yl)phenylbenzidine Synthesis&gt; _ 4,4,5,5-tetradecyl-2-(3-(10-(naphthalen-1-yl)fluoren-9-yl)phenyl)- Γ) ' 1,3,2-dioxo 2.02 g of heteroborane, 0.83 g of 3-bromo-4-indolylpyridine, 0.14 g of tetrakis(triphenylphosphine)palladium(0), 1.70 g of potassium phosphate, 20 mL of pseudocumene, 5 mL of third butanol and water 1 mL was placed in a flask, and the mixture was stirred under a nitrogen atmosphere at reflux temperature for 6 hours. The reaction solution was cooled to room temperature, and water and toluene were added for liquid separation. The solvent was evaporated under reduced pressure, and the obtained solid was purified by silica gel column chromatography (yield: benzene/ethyl acetate = 95/5). The eluate is passed through a column of activated carbon to remove the coloring component. The eluate was concentrated under reduced pressure, and heptane was added to reprecipitate to give 4-mercapto-3-(3-(10-(naphthalen-1-yl)indol-9-yl)phenyl)acridine 1.06 g. . 〇^-NMR (CDCls): 6=8.6 (d, lH) '8.5 (dd, 1H)'8.1 (d, 1H), 8.0 (dd, 1H), 7.8 (d, 2H), 7.8~7.7 (m , 2H), 7.6 to 7.4 (m, 7H), 7.4 to 7_3 (m, 2H), 7.2 to 7.1 (m, 5H), 2.4 (d, 3H). [Synthesis Example 12] Synthesis of Compound (1-2-172) &lt;3-mercapto-5-(3-(10-(qin-1-yl)en-9-yl)phenyl)'1 to 11 Fixed synthesis &gt; 91 201229203 HUOI jpill is No. 100142814 Chinese manual without slash correction. Amendment date: March 15th, 2011 will be 4A5,5_tetradecyl-2-(3_(10_(naphthalenyl)- -9-yl)benzene Base) -1,3,2-dioxaborane 2.02 g, 3-bromomethylpyridinium 83 g, tetrakis(triphenylphosphine), (0) 0.14 g, linolenic acid, 1.70 g, pseudocumene 2 blush, third butanol 5 mL and water i mL were placed in a flask, and sparged for 6 hours under a nitrogen atmosphere at reflux temperature. The reaction solution was cooled to room temperature, and water and toluene were added to separate. The solvent was removed by depressurization, and the obtained solid was purified by silica gel column chromatography (eluent: fbenzene / - = 95/5). The eluate is passed through a column of activated carbon to remove the coloring component. The eluate was concentrated under reduced pressure, and the mixture was added to a heptane to be re-supplemented to obtain a phenyl group of 5-(3-(1〇-(naphthalen-1-yl)) phenyl). NMR (CDC13): 5 = 8.8 (d, 1H) , 8.5^8.4 (m, 1H) &gt; 8.1 (d, 1H), 8_0 (d, 1H), 7.8~7.7 (m, 7H), 7 6 ( m, 2H), 7 5 (m, 3H), 7.3 (t, 2H), 7.3 to 7.2 (m, 4H), 2 4 (d, 3H). The raw material compound can be appropriately changed, and the above synthesis example can be used. The method of synthesizing other derivative compounds of the present invention. "The following are examples of organic &amp; elements using the compounds of the present invention, and the present invention will be described in more detail, but the present invention is also exemplified in the examples. In the organic EL device of Comparative Example i, (4) the measurement of the time (f) of the initial current driving test towel _ lacking (V), maintaining the initial brightness of 90% or more, and the brightness (five). The material compositions of the respective layers in the fabricated electroluminescent device of Example 1 and Comparative Example 2 are listed in Table 1 below. Hole injection layer example 1 HI ~[ 92 201229203 HUO I jpifl is 100142814 Chinese manual without scribe correction This revision date: March 15, 101 Comparative example 1 丨 HI I NPD - work ΐ ^ ^ (Α) 丨Compound surface|Compound (C)] In Table 1, 'HI' is N4, N4'-diphenyl-Ν4, Ν4, Κ9_phenyl_9H_ π-carzol-3-yl)-[1, Γ- Biphenyl]-4,4'-diamine, "npd" is hydrazine, hydrazine, -diphenyl-hydrazine, Ν'-dinaphthyl-4,4'-diamine linkage, compound 9-benzene The compound (8) is Ν5, Ν5, Ν9, Ν9-7,7·hexaphenyl-7Η-benzo[c]芴-5,9- The diamine 'compound (C) is 9,10-bis(tetradecyl-2-yl)naphthalen-1-yl)anthracene. The chemical structure of these compounds and the 8_ used when forming the cathode According to Liq, the same is expressed as follows. NPD Compound (C) [Example 1] A glass substrate (manufactured by 〇pt〇Science, Inc.) of 26 mm&gt;&lt;28 mm x 〇.7 mm obtained by sputtering a 180 nm thick ITO which was sputtered into a film to 150 nm As a transparent support substrate, it is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Vacuum Co., Ltd.), and a molybdenum-made vapor deposition boat in which HI is placed, a molybdenum-made vapor deposition boat in which NPD is placed, and a compound are placed. (A) Indium-made vapor-deposited boat, 93 201229203 WOl jpux Revision date: March 15, 2011, No. 100142814 Chinese specification No straight-line correction This is a molybdenum-made vapor-deposited boat in which compound (B) is placed, and the compound is placed ( 1-M) Molybdenum-based clock boat, Liq's steaming key boat, silver shovel steamer, and magnesium molybdenum steaming boat. The following layers were sequentially formed on the ITO film of the transparent supporting substrate. The vacuum tank is decompressed to 5xlG4 Pa, and the steaming boat is heated and twisted to fill the hole injection layer with a thickness of 40 nm, and then heated into a steaming boat of NpD, and the mine is 25 nm thick. A hole transport layer is formed. Then, the vapor deposition boat of the object (4) and the boat of the release compound (8) are simultaneously added and steamed to the film nm to form a light-emitting layer. At this time, the vapor deposition rate was adjusted so that the weight ratio of the compounds (A) and (9) was /. Next, the therapeutic boat that was placed in the chemical solution was heated to a film thickness of 25 nm to form an electron transport layer. The evaporation rate of each layer is _ Cong/Qing. It is heated and put into the steaming boat of Liq, and is plated with 〇_~〇3 fine/coffee= to the film thickness to become i nm, and then heated to put the silver-based money boat into the steaming boat, with silver and The atomic ratio of magnesium is about 0.01 to 10 nm/sec to adjust the vaporization rate, and the evaporation is fine to form a cathode, and an organic EL element is obtained. The money is 100 steps like =7, =? as the anode. The Llq silver alloy electrode is used as the ^ pole. When a voltage is applied, a blue wavelength of about 455 nm is obtained. And by using a current density of 2000 cd/m2 to obtain an initial brightness; :: application: flow drive test. The driving test starting voltage is 4; V? The time of the brightness of 9Q% or more of the knife degree is Μ &lt;Comparative Example 1 &gt; Substance (1-1-1) is replaced by compound (c), and otherwise based on 94 201229203" IV/WA ^ iL X Revision date: 1〇1年月月〗 5日为100142814号The method of the second example is modified to obtain an organic EL element. The IT 〇 electrode is used as an anode, and the Llq/Zhen 曰 silver iridium electrode is used as a cathode, by using an electric rider to obtain an initial luminance of 0 cd/m. The actual ratcheting current axis test. The driving test starting voltage is 3.73 V, and the initial brightness is tilted. Take time for 1 hour. The above results are summarized in Table 2. Table 2 Electron transport layer "- 90% of the time of the knife shell (hr) 71 Starting voltage (V) 实例 Example 1 Compound (1-1-1 Plant Comparative Example 1 Compound (C) - 1 3.73 Further, in the organic EL devices of Examples 2 to 12 and Comparative Examples 2 and 3, the driving start voltage (V) in the constant current driving test and the time (5) in which the luminance was maintained at 90% or more of the initial value were used. Measurements. Examples and comparative examples are described in detail below. The material compositions of the layers of the organic EL elements of Examples 2 to 12 and Comparative Examples 2 and 3 which were produced are shown in Table 3 below. ------ Hole injection layer Electron hole transport layer luminescent layer electron transport layer host dopant - Example 2 HI ΗΤ Compound (D) Compound 〇 E) Compound (1-1-1) Example 3 HI HT Compound Compound (E) Compound (1-1-2 Example 4 ------ HI ΗΤ Compound (D) Compound (1-1-134) HI HT Compound (D) Compound (E) Compound (1-1-153) _ nwj 〇HI ΗΤ Compound (D Compound (E) Compound (1-1-172) 7 HI HT Compound (D) Compound (E) Compound (1-1-191) _ Άιη δ HI HT Compound (D) Compound (E) (1-1-210) X Example 9 HI HT Compound (D) Compound (E) Compound (1-1-229) _XW|^l〇HI HT Compound (D) Compound (E) Compound (1-2- 1) j^Lll HI HT Compound (D) Compound (E) Compound (1-2-153) Shell Example 12 HI HT Compound (D) Compound (E) Compound (1-2-172) 95 201229203 *τνυ a ^ Jjxxx is 100142814 Chinese manual without slash correction. Amendment date: 1 3 1 March 15th Comparative Example 2 HI HT Compound (D) Compound (E) Compound (F) Comparative Example 3 HI HT Compound 〇D) Compound ( E) Compound (G) In Table 3, "HI" is N4, N4'-diphenyl-N4, N4'-bis(9-phenyl-9H-carbazol-3-yl)-[1,1 '-Biphenyl]-4,4'-diamine, HT is Ν-([1,Γ-biphenyl]-4-yl)_9,9-didecyl-indole-(4-(9-phenyl) -9Η·oxazol-3-yl)phenyl)-9Η-indol-2-amine, compound (D) is 9-(4-(naphthalen-1-yl)phenyl)-l〇-phenylhydrazine, The compound (Ε) is 4,4'-((7,7-diphenyl-7Η-benzo[c]indole-5,9-diyl)bis(phenylamino))dibenzonitrile, compound (F) is 4,-(4-(10-(naphthalen-2-yl)fluoren-9-yl)phenyl)-2,2':6',2"-terpyridine, compound (〇) is 5 -(4-(10-(naphthalen-1-yl)) -9-yl)phenyl A 26 mm&gt;&lt;28 mm x 〇.7 mm glass substrate (manufactured by Opto Science, Inc.) having a 180 nm thick ITO sputtered to a thickness of 150 nm was used as a transparent supporting substrate and fixed to a commercially available steamed ore. Device (made by Showa Vacuum Co., Ltd.) [Example 2] 96 201229203 woupifl Revision date: 1 March 1st, March 15th is 100142814 Chinese manual without scribe line correction, on the holder, install HI indium steaming Mine boat, steaming boat made of molybdenum in the town, steaming boat made of molybdenum in compound (D), pinned in compound, plated, and compounded (1)] Into the ❿ ❿ 奈 奈 奈 、 、 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , The following layers were sequentially formed on the ITO film of the transparent supporting substrate. The vacuum chamber is depressurized to 5XM Pa. Firstly, the HI is steamed, and the oil is evaporated until the film thickness becomes 0 nm to form a hole injection layer. The second step is to heat the plated boat into the town, and the plate is thickened to a film thickness. It becomes 30 nm to form a hole transport layer. Then, the vapor deposition boat in which the compound (E) was placed and the crucible-plated boat in which the compound (F) was placed were heated, and the film thickness was 35 nm to form a light-emitting layer. At this time, the vapor deposition rate was adjusted so that the weight ratio of the chemical substances (D) to (E) was about 95:5. ^ times, at the same time, the evaporation boat placed in the compound (丨·^) is placed and placed in the treatment key boat, and the antimony ore is brought to a film thickness of 25 nm to form an electron transport layer. The vapor deposition rate was adjusted so that the weight ratio of the chemical substance (1-1-1) to Liq became about 1:1. The vapor deposition rate of each layer was 〇.〇1 to 丨nm/sec. Thereafter, 'heating the vaporized boat placed in Liq, vapor-depositing at a speed of 0.01 to 0.1 nm/sec until the film thickness becomes 1 nm, and simultaneously heating into a boat of magnesium and a boat of silver, in silver. The vapor deposition rate was adjusted between 0.1 and 10 nm/sec in a ratio of 1:10 to magnesium, and vapor deposition was carried out until the film thickness became 100 nm to form a cathode, thereby obtaining an organic EL device. For example, if the IT0 electrode is used as the anode and the Liq/magnesium-silver alloy electrode is used as the cathode, the blue light emission with a wavelength of about 450 nm is obtained. Moreover, a constant current drive test was carried out by using a current density of an initial luminance of 2000 Cd/m2. The driving test starting voltage is 3.89 V, and the initial brightness is maintained. 97 201229203 WOl jpm Corrected period: 】 0] March 〗 5 曰 100142814 Chinese manual without scribe correction The time of 90% or more brightness is 61 hours. [Example 3] An organic &amp; member was used based on the actual compound except that the compound (1)1·1) was replaced by the compound (1-1_2). The current is a driving test with a 〇 electrode as the anode and (4) 222 J cathode '" with a starting brightness of 2000 cd/m2. The driving test starting voltage is 3.79 m and the brightness of 9 G% or more is reduced. 60 hours. Example t compound (1M) is replaced by compound (i_i_i34), based on Γϋυ organic EL element. The 1τ〇 electrode is used as the anode, and (4) f can obtain the initial brightness 2-4 current V, accompanied by pull, &amp; I catch the crane. The starting voltage of the driving test is 3.86 [the time of the brightness of the actual brightness of 9〇% or more is 177 hours. The example is t (1 hour is replaced by the compound (ι-Μ53), based on the money-silver In this case, the organic &amp; components are used. The anode electrode is used as the anode, and the Liq/density is the bucking pole'! The initial current of 2000 cd/m2 is obtained, and the turbulent flow driving test is performed. The driving test starting voltage is 3.87 [Example, 6] The initial redness time of 9〇% or more is 101 hours. In addition to the example compound (1 υ to compound (1) 1.172), an organic EL element is obtained based on the Wei alloy. 1Τ〇 electrode is the anode, (4) density; / ^ is the cathode, and the current with the initial brightness of 2_ cd/m2 is only mutually constant current Dynamic test. Driving test starting power is Μ 98, xfl 201229203 Revision date: March 15, 2011 is 100142814 Chinese manual without scribe line correction V, maintaining the initial shell degree 90% brightness for 87 hours [Example 7] An organic a-component was obtained by the method of Example 2 except that the compound (M-1) was replaced with a compound (丨小191). The IT〇 electrode was used as the anode, and (10) the silver alloy electrode was used as the cathode. A constant current drive test was performed on the current consultation with an initial luminance of 2 〇〇〇 cd/m 2 . The starting voltage of the driving test was 3·57 Ο 〇V, and the initial luminance was maintained at 9 〇. The time of the above luminance was 2 〇 3 Small [Example 8] An organic EL device was obtained by the method of Example 2 except that the compound (1-1-:!) was replaced with a compound (1 small 21 Å). The ruthenium electrode was used as the anode, Uq/silver gilt The electrode sugar pole' is subjected to a constant current drive test with a current control of the initial brightness of 2_Qin2. The test starting voltage is (4) v, and the time for maintaining the initial brightness of 90% or more is n [Example 9] ^ • Example 2 is replaced by a compound (M, other than, based on the shellfish side The organic EL element was obtained by using an IT 〇 electrode as a cation alloy to obtain an initial luminance of 2 _ (10); and a driving test. The driving test was started at 3.67 =] the brightness was 8. The time was except for the compound (1). - An organic EL device was obtained by changing to a compound (mountain). The enthalpy current drive test was carried out with a 1 τ electrode as a positive density. Start of driving test 99 201229203 HUOl jpui Revision date: March 15, 101 For the Chinese manual of 100M2814, there is no slash correction V, and the initial shell degree is 9〇〇/. The above brightness time is 57 hours. [Example 11] Except that the compound (1-1-1) was replaced by the compound (丨_2_153), the organic EL device was obtained by the method of Example 2, using the Ιτ〇 electrode as the anode and the (iv) silver alloy electrode as the cathode. A constant current driving test was performed with a current intensity of 2 〇〇〇 cd/m 2 of initial luminance. The driving test starting cake was... V ′ The time for maintaining the initial brightness of 9 G % or more was 6 2 . · [Example 12] , = Compound (1_M) is replaced by compound (1_2_m), based on which there is a component. The 1το electrode is used as the anode, (4) the six stores: / the electrode is the cathode' to obtain the initial luminance of 2000 cd/m2 = only the fine constant current driving test. Driving test = the time of holding the brightness above the initial brightness gauge is 2:: &lt;Comparative Example 2&gt; The method of "::::1:1-1) is replaced by the compound (F), based on the example A f organic El TL pieces. Taking the IT0 electrode as the anode, The second is the cathode, and the flow is driven by the current with the initial brightness of the bladder (10)2. The driving test starting voltage is 5.35 V, and the time of holding the initial error of 9 G% or more is 2 V &lt;Comparative Example 3 &gt; square == z) is replaced by the compound outside. The example-based alloy electrode uses 1το electrode as the anode, Llq heart implementation of the initial electricity can get the initial brightness 2_heart 2 current density", motor drive test. The driving test starting voltage is 4 20 VH 100 201229203 HUOI jpifl Correction date: 1〇1年1月15日100142814号 Chinese manual No sizing correction The brightness of the initial brightness of 90% or more is 30 hours or more. In Table 4. Table 4 产业 [Industrial Applicability] According to a preferred aspect of the present invention, it is possible to provide an organic electroluminescence device which particularly improves the lifetime of a light-emitting element and has a good balance with a driving voltage, and has an organic electroluminescence element. A display device, an illumination device having the excitation light element, and the like. Electromechanical [Simple description of the diagram] Benefits. [Main component symbol description] None. 101 201229203 H-UO 1 jpiil is lOOl428〗 No. 4 Chinese manual no slash correction This correction date heart engine: Invention patent description (this specification format, order, do not change anything, please do not fill in the ※ part) ※Application No.: ※Application曰: Classification: 1. Invention Name: (Chinese/English) Electron transport material and organic electroluminescence device using it / ELECTRON TRANSPORT MATERIAL AND ORGANIC 〇electroluminescent device using the same II. Chinese Abstract: The present invention The compound represented by the formula (1) is characterized in that it is stable even when a voltage is applied in a thin film state and has high charge transport property, and is suitable as a charge transport material for an organic EL element. The electron transporting material is used for the electron transport %/or electron injecting layer of the organic EL element to obtain a long-life organic EL element. 〇(1) =式” is a shouting base. Any hydrogen in Guanxian can be replaced by % thiol, benzyl, 1-methyl or 2-naphthyl, phenyl, pucayl and naphthyl can be- The step is replaced by a silk or a loop wire; R rides, burns a base, a base or an aryl group. Any hydrogen in the aryl group can be substituted by a burnt group or a ring wire. Abstract: This invention provides!! 〇Λ , Ρ 0_eS a comp〇und 〇f f_ula (1 201229203 Revision date: 1 March 1st, March 15th is 10 (^142814 Chinese manual no line correction) which is characterized in being stable to voltage application even in a film state and Having high charge transportability and planning serves as a charge transport material of an organic electroluminescent (OEL) device. By applying the electron transport material to the electron transport layer and/or the electron injecting layer of an OEL device, the lifetime of the OEL device Can be logner. In formula (1), Py is pyridyl, where hydrogen may be replaced by alkyl, cycloalkyl, phenyl, 1-naphthyl or 2-naphthyl, and the phenyl, 1-naphthyl or 2-naphthyl may be substituted with alkyl or cycloalkyl. R is hydrogen, alkyl, cycloalkyl or aryl, where hydrogen is hydrogenated in the aryl may be replaced by alkyl or cycloalkyl. IV. Designated representative map: (1) The representative representative of the case is: None. (2) A brief description of the symbol of the representative figure: None. 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 201229203 HUOl jpiil _ is 100142814 Chinese manual without line correction This amendment date: 1 March 1st, 15th, 7th patent application scope: 1. a compound, In the formula (1), which is represented by the following formula (1), Py is a bite group, and the n is an alkyl group having a carbon number of 6 or a cycloalkyl group having a carbon number of 3 to 6 in an arbitrary ratio of the pyridine group. a phenyl group substituted with a carbon number of 66 or a cycloalkyl group having 3 to 6 carbon atoms, a 1-naphthyl group substituted with an alkyl group having a carbon number of 66 or a cycloalkyl group having a carbon number of 3 to 6. Or substituted with a C 1 - 6 alkyl group or a C 3 - 6 cycloalkyl substituted 2-naphthyl group; R is hydrogen, a C 1 to 6 alkyl group, and a carbon number of 3 to 6 ring An alkyl group or an aryl group having 6 to 14 carbon atoms, and any hydrogen in the aryl group may be substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms; At least one hydrogen in the compound of the formula (1) may be substituted by deuterium. 2. The compound according to claim 1, which is represented by the following formula (1-1) or (1-2), In the formulae (M) and (1-2), Py is a ratio of D to a bite base. Any hydrogen in the bite group may be a hindered group having a number of 1 to 6 and a cycloalkyl group having a carbon number of 3 to 6. Carbon number 6 alkyl or carbon number 3~6 102 201229203 &quot;rvoi^pifl is 100142814 Chinese manual no face correction This revision date: March 15th, 2011, the cyclic phenyl group substituted phenyl, carbon number a 1-naphthyl group substituted with a decyl group of 1 to 6 or a cycloalkyl group having 3 to 6 carbon atoms, or a 2-naphthyl group substituted with a decyl group of 6 to 6 or a cycloalkyl group having 3 to 6 carbon atoms Substituting; R is hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or an aryl group having 6 to 14 carbon atoms, and any hydrogen in the aryl group may be alkyl group having a carbon number of 丨Or a cycloalkyl group having 3 to 6 carbon atoms; and at least one hydrogen in the compound of the formula (1-1) or (1-2) may be substituted by deuterium. 〇3· The compound according to the item 2, wherein Py is a 2-β ratio bite group. 4. The compound according to claim 1 or 2 wherein py is a 3-α ratio bite group. a compound according to 1 or 2, wherein py is 4-° to bite. 6. If applying The compound according to item 1 or 2, the range of interest, where Py is selected from the group of a monovalent, 7. The compound according to claim 1 or 2, which is selected from the group consisting of the following formulas (1 small 1), (1-1-2), (1-1-3), (MW#, (1) 153), (1-1-172), (1-1-191), (1-1-210), (ι_ι·229), (1-2-1), (1-2-153) and (1-2-172) One of the groups of the compounds listed, 103 201229203 HUO 1 a is 100142814 Chinese manual without scribe correction This revision date: 1〇1年月月15曰 (1-1-1) (1-1-3) (1-1-153) (1-1-191) β (1-2-1) N (1-2-172) Me, 8. An electron transporting material comprising the compound according to any one of claims 1 to 7. 104 201229203 &quot;+υοι jpifl is 100142814 Chinese manual without scribe correction. Amendment date: March 1, 2014. 9. An organic electroluminescent device comprising: an anode and a cathode - opposite electrode, arranged in An illuminating layer between the pair of electrodes, and an electron transporting layer and/or an electron injecting layer disposed between the yin and the illuminating layer and containing a transporting material as described in claim 8 of the full application. 10. The organic electro-active device according to claim 9, wherein at least 2 of the electron transport layer and the electron injecting layer are selected from the group consisting of a contact metal complex and a joint derivative. At least one species of the group consisting of a substance, a substance, and a borane derivative. The organic electric parts described in the 1G item of the Zhusheng 11 soil application patents include at least: the light transport layer and the electron injection layer are at least selected from the group consisting of metal, earth metal, rare earth metal, and gold. Metal sulphide, soil test metal oxide, soil test compound, oxide of rare earth metal, complex of rare earth metal, test, compound, compound, earthworm, money, and rare earth metal At least one of the groups consisting of organic errors. Organic complex 105 201229203 Amendment date: March 15th, 1st, 1st, 10th, 1st, 142,814, Chinese text, no slash correction, which is characterized in being stable to voltage application even in a film state and having high charge transportability and planning serves as a By applying the electron transport material to the electron transport layer and/or the electron injecting layer of an OEL device, the lifetime of the OEL device can be logner. In formula (1), Py is pyridyl, where hydrogen may be replaced by alkyl, cycloalkyl, phenyl, 1-naphthyl or 2-naphthyl, and the phenyl, 1-naphthyl or 2-naphthyl may be substituted with alkyl or cycloalkyl. R is hydrogen, alkyl, cycloalkyl or aryl, where hydrogen is hydrogenated in the aryl may be replaced by alkyl or cycloalkyl. IV. Designated representative map: (1) The representative representative of the case is: None. (2) A brief description of the symbol of the representative figure: None. 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 201229203 jl is the Chinese manual of 100142814 without a slash correction. Amendment date: March 15, 101 3