TW201226394A - Electron transport material and organic electroluminescent device using the same - Google Patents

Abstract

A compound represented by formula (1) of the present invention is utilized to be an electron transport material of an organic electroluminescent device, and the use of the electron transport material can make contributions like prolonging the life of the organic electroluminescent device. In formula (1), Py independently represents the group represented by formula (2), (3), or (4); m and n is 0 or 1, m+n=1; and in formula (1), at least one hydrogen of the benzene ring, naphthalene ring and pyridine ring is replaced by C1-C6alkyl or C3-C6 cycloalkyl.

Description

201226394 VI. Description of the Invention: [Technical Field According to the Invention] An electron transfer wheel (for T, there is a novel material having a π-bite base, and an organic electroluminescence element using the electron transport material) In recent years, in recent years, the money EL element has been studied for the next generation (func〇 lor flat panel display) and has been studied. In order to promote the real-life of the organic EL element, the low-level operation and the longevity of the life-saving elements are indispensable. Now, these factors, the industry, are directly developing new electronic transmission materials. 2 = The driving force of the blue component is reduced and the life is extended. The patent & (Japanese Patent Laid-Open Publication No. 20 〇 3·1239 δ 3) describes the case as a phenanthroline derivative or an analog thereof. 2, 2' ♦ (4) compound secret electron transport material The organic EL TL device can be driven at a low voltage. However, the element characteristics (driving voltage, luminous efficiency, etc.) reported by the examples of this document are only relative values based on comparative examples, and actual measured values which can be judged to be practical values are not described. Further, an example in which a 2,2,-bipyridyl compound is used for an electron transporting material is disclosed in Non-Patent Document 1 (Proceedings of the 10th International Workshop on

Inorganic and Organic Electroluminescence, the 10th International Symposium on Inorganic and Organic Electroluminescence, and Patent Document 2 (Japanese Patent Laid-Open Publication No. 2002-158093) and Patent Document 3 (International Publication No. 2007/86552) disclose. The low Tg of the compound 201226394 described in Non-Patent Document 1 is not practical. Although the compound described in Patent Document 2 and Patent Document 3 can drive the organic EL element at a relatively low voltage, it is expected to further extend the life in practical use. [PRIOR ART DOCUMENT] [Patent Document 1] Japanese Laid-Open Patent Publication No. 2003-123983 (Patent Document 2) Japanese Patent Laid-Open Publication No. Hei No. Hei. 86552 manual [Non-patent literature] [Non-Patent Document 1] Proceedings of the 1〇* Internati〇nal shop 〇n Inorganic and Organic Electroluminescence (2000) (The 10th International Symposium on Inorganic and Organic Electroluminescence (2000)) SUMMARY OF THE INVENTION The present invention has been developed in the field of the prior art. The problem of the month is to provide an electron transport material that contributes to the life extension of the organic EL element. Further, the present invention has been made in an object of providing an organic EL device using the electron transporting material. After eight studies by eight people and others, it was found that at least one nitrogen on the 6 phenylene naphthalene ring was obtained by having any of the following == phenyl groups; The present invention was completed based on the discovery, in place of the compound 201226394, which is a loop wire having an anisotropy of 1 to 6 or a carbon number of 3 to 6. The above problem is solved by the following items [1] a compound represented by the following formula (1).

Py is independently a group represented by the formula (2), (3) or (4); <}-〇-^0 (2) ... n is 0 or 1, m + n: , * 1 Al 1 » jim_ At least one hydrogen on the benzene ring, the naphthalene ring and the acridine ring in 5 # a ( j丨,) is a carbonyl group of 1 to 6 or a cyclodext group having a carbon number of 3 to 6. n The compound according to the above [1], which is represented by the following formula (1-1), 丄-2),

201226394 In the formulas (1-1) and (1-2),

Py is a group represented by the formula (2), (3) or (4);

And at least one hydrogen on the stupid ring, the naphthalene ring and the η-pyridine ring in the formulae (M) and (1-2) is substituted with an alkyl group having a carbon number of 1 to 6 or a ring having a carbon number of 3 to 6 alkyl. [3] The compound according to the above [1], which is represented by the following formulas 0-3), (1-4), (1-5), or (1-6).

In the formula (1-3) to (1-6),

Py is a group represented by the formula (2), (3) or (4); Ό -Ck!) (2) (3) (4) 7 201226394 and benzene in the formula (1-3) to (1-6) At least one hydrogen on the ring, naphthalene ring and acridine ring is substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms. [4] The compound according to the above [1], which is represented by the following formula (丨_7) or (u),

In the formulas (1-7) and (1-8),

Py is a group represented by the formula (2), (3) or (4); (2) (3) (4) R is a group having a carbon number of 1 to 6 or a ring having a carbon number of 3 to 6 And I, p is an integer from 1 to 5. [5] The compound according to the above [nth item, which is represented by the following formula (or (1-10),

II 201226394 In the formula (^9) and (ι_ι〇),

Py is a group represented by the formula (2), (3) or (4); -C) is i) ^0 (2) (3) (4) R is a carbon group having a carbon number of 1 to 6 or a carbon number of 3 to 6 And a q is an integer of 1 to 5. It is represented by the following formula (1-11) or [6] as the compound (1-12) described in the above [1],

In the formulas (1-H) and (1_12),

Py is a group represented by the formula (2'), (3') or (4');

In the formulae (2'), (3), and (4'), R is an alkyl group having a carbon number of j 6 or a cyclic alkyl group having a carbon number of 3 to 6 in 201226394; and s is an integer of i 4 . [7] The compound according to the above [丨], which is represented by the following formula (1-13) or (1-14),

In equations (1-13) and (1_14),

Py is a group represented by the formula (2'), (3') or (4');

In the formula (2'), (3,) or (4,), R is an alkyl group having a carbon number of 〜6 or a cycloalkyl group having a carbon number of 3 to 6; and, s is an integer of j 4 . [8] The compound according to the above [丨], which is represented by the following formula (1-15) or (1-16),

201226394 4U55Upif type (1-15) and (1-16),

Py is a group represented by the formula (2), (3) or (4);

R is an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms; and t is an integer of 1 to 4. [9] The compound according to [1] above, which is represented by the following formula (1-7-26)

[10] The compound according to the above [1], which is represented by the following formula (1-7-74)

[11] The compound according to the above [1], which is represented by the following formula (1-7-98) 11

201226394 HUJ

[12] The compound according to [1] above, which is represented by the following formula (1-7-96)

[13] The compound according to [1] above, which is represented by the following formula (1-14-14)

[14] The compound according to the above [1], which is represented by the following formula (M1-1), (1-11-2), (1-11-3), (M1-4), (1-11). -5), (1-11-6), (1-11-8), (1-11-18), (1-11-39), (1-14-2), 12 201226394 (1-14 -3 ), ( 1-14-11 ), ( 1-14-12), ( 1-14-13), ( 1-14-15), (1-14-16), (1-14-17 Any one of (1-14-18), and (1-14-20)

13 201226394

[15] An electron transporting material comprising the compound according to any one of the above [1] to [14], wherein the one of the ones of the ones of the above-mentioned. [16] 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; and a cathode disposed between the cathode and the light-emitting layer and containing the above The electron transport layer and/or the electron injection layer of the electron transport material according to [15]. The organic electroluminescent device of the above-mentioned item [16], wherein at least one of the electron transport layer and the electron injecting layer further comprises a metal conjugate selected from the group consisting of a hydroxy phthalocyanine metal complex and a π ratio bite derivative At least one of the group consisting of a morphine derivative and a rotten derivative. [18] The organic electroluminescent device of the above-mentioned [16] or [17], wherein at least one of the electron transport layer and the electron injecting layer further comprises a metal selected from the group consisting of a metal, an alkaline earth metal, a rare earth metal, and a genus Oxide, metallurgical, chemical, earth metal oxide, earth metal halide, rare earth gold, rare earth metal halide, alkali metal organic complex, group complex and rare earth metal organic L 53⁄4 % 叼 double fruit composed of the complex compound. Further, even if a voltage is applied in a thin film state, it is stable and used as a feature. The compound suitable for use in the present invention is used in organic EL and is difficult to transfer. According to the present invention, it is possible to produce a full-piece display device by using the EL element of the layer, and the EL device of the present invention. 201226394 4〇550pif Hereinafter, the present invention will be described in more detail. In the present specification, for example, "the compound represented by the formula (1-7-26)" may be referred to as "the compound (1-7-26)". The compound represented by the formula (1_7·74) is sometimes referred to as "compound (1-7-74)". The symbols and formulas of other formulas are also the same. <Description of the Compound> The first invention of the present invention is a compound having a thiol group, a bipyridyl group or a pyridylphenyl group represented by the following formula (1).

(2) (3) (4) In the formula (1), Py is independently represented by the formula (7), (3) or (4), and m and n are 〇 or bm + d. And the benzene in the formula (1) is not coated with pyridine. The substitution of at least one hydrogen on the oxime to a group having a carbon number of 1 to 6. or a cycloalkyl group having a carbon number of 3 to 6 is a feature of the present compound. The pyridyl group represented by the formula (2) is specifically a 2·pyridyl group or a pyridyl group. Set the foundation. The bipyridyl group represented by the formula (3) is specifically a 2,2,-biindole-5-yl 2,2'-linked ratio. _6-based, 2,2,-linked t-1,4-yl, 2,3,,π ratio bite _5_ base, 2 joint ratio. -6-based, 2,3, _ _ _ _ _ 4 _ base, 2, 4, let the bite _5_ base, soil 2, heart

16 201226394 40550pif Pyridine-6-yl, 2,4'-bipyridin-4-yl, 3,2'-bipyridyl-6-yl, 3,2,-bipyridyl-5-yl, 3,3' - 联 ° bit -6 · base, 3, 3 '- ̄ ° ° bite 5--base, 3, 4, _ _ _ _ _ D--6-yl, 3,4'-bipyridin-5-yl, 4,2,-bipyridin-3-yl, 4,3'-bipyridin-3-yl, or 4,4'-linked Bipyridin-3-yl. The fluorenylphenyl group represented by the formula (4) is specifically 4-(2-pyridinyl)phenyl, 4-(3-pyridyl)phenyl, 4-(4-pyridyl)phenyl, 3-(( 2_pyridyl)phenyl, 3-(3-acridinyl)phenyl, 3-(4-oxaridinyl)phenyl, 2-(2-pyridyl)phenyl, 2-(3- N-pyridyl)phenyl, or 2·(4_β-pyridyl)phenyl. In the formula (1), the position at which Py is bonded may be any position on the phenyl group or the 2-naphthyl group. The position is preferably 4 and 3 on the phenyl group, and preferably the position on the 2-naphthyl group. And 7 digits. In terms of not expanding the conjugated system and not lowering the energy level of the lum〇 (lowest unoccupied molecular orbital ‘ minimum unoccupied molecular orbital domain), it is particularly preferred to be the 3-position of the phenyl group. Further, in terms of easy availability of the raw material, it is particularly preferably a 6-position of 2-naphthyl group. Examples of the benzene ring, the naphthalene ring, and the alkyl group having 1 to 6 carbon atoms substituted in the pyridine ring in the formula (1) are: methyl 'ethyl, n-propyl, isopropyl, n-butyl, and iso- Butyl, tert-butyl, n-pentyl, isopentyl, 2,2-dioxime, n-hexyl, and isohexyl. Its succinct base is methyl, ethyl, ~6 ~ Μ Μ and second butyl. Examples of the soil burnt group having a carbon number of 36 are cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. If the raw material is obtained and the ease of synthesis is taken into consideration; s:, the ring-burning group is a rainbow base. *The compound of the 'Yujia' is the following formula ((4) or (called 17 201226394)

The definitions of Py in the formulae (1-1) and (1-2) are the same as described above. More specifically, the compound represented by the formula (〇) is a compound represented by any one of the following formulas (Bu 3) (1-6).

The definition of Py in the formulae (1-3) to (1.6) is the same as described above. The compound represented by the formula (1) is more specifically a compound represented by any one of the following formulas (17) to (1).

201226394 HUD^Upif

The definitions of Py and R in the formulae (1-7) to (MO) are the same as described above. In the formulae (1-7) and (1-8), p is an integer of 1 to 5, preferably an integer of 1 to 2' is more preferably 1. The position of the phenyl group substituted by R is not limited, and is preferably 3 or 4 positions. q in the formulae (1-9) and (1-10) is an integer of 1 to 5, preferably an integer of 1 to 2, more preferably 1. The position of the naphthyl group substituted by R is not limited to the position of 6 or 7 positions. Further, the compound represented by the formula (1) is more specifically a compound represented by any one of the following formulas (1-11) to (M4).

19 201226394 40550pif The definition of Py1 in the formulas (1-11) to (1-14) is the same as described above. The definition of R in the above formula (2〇, (3') or (4〇 is the same as above. s is an integer of 1 to 4, preferably 1 or 2, more preferably 1. Pyridyl group substituted by R. The compound represented by the formula (1) is more specifically a compound represented by the following formula (1-15) or (1-16).

The definitions of Py and R in the formulae (1-15) and (1-16) are the same as described above. t is an integer of 1 to 4, preferably 1 or 2, more preferably 1. The position of the phenyl group substituted by R is not limited, and in view of the ease of synthesis, in the case of 1,4-phenylene, the position is preferably 3 in terms of carbon bonded to hydrazine. In the case of a 1,3-phenylene group, it is preferably 4 positions based on the carbon bonded to the hydrazine. Specifically, the compound represented by the above formula (1) is roughly classified into the compounds represented by the formulae (1-7) to (1-16). Among these, preferred structures are the formula (1-7), the formulas (1-9) to (1-11), and the formula (1-13) to (1-16), and the more preferable structure is the formula (1). -7). <Specific Example of Compound> Specific examples of the compound of the present invention can be disclosed as the following formulas, but the present invention is not limited to the disclosure of these specific structures. 20 201226394 4imupif <Specific Example of Compound represented by Formula (1-7)> Specific examples of the compound represented by Formula (1-7) are, for example, the following formula (1-7-1) to (1-7-144) ) shown. Among these, preferred compounds are of the formula (b-7)~(Bu 7-6), formula (1-7-10)~(1-7-12), formula (1-7-16)~ (1-7-30), formula (Bu 7_34) ~ (H36), formula (1-7-40) ~ (1-7-48), formula (1-7-73) ~ (1-7-78 ), formula (1-7-82)~(1-7-84), formula (1-7-88)~(Bu 7_102), formula (1-7-106)~(1-7-108) and Formula (1-7-112) ~ (1-7-120).

(1-7-9) 21 201226394 40550pif (1-7-11)

22 201226394

(1-7-32) (1-7-33) 23 201226394 4U»Upif

24 201226394 40550pif

(1-7-47)

25

201226394t I \y ij l L

201226394

27 201226394 40550pif

28 201226394 40550pif

29 201226394 40550pif

30 201226394 40550pif

31 201226394 40550pif

Specific examples of the compound represented by the formula (1-8) > Specific examples of the compound represented by the formula (1-8) are, for example, the following formula (1-8-1) to (1-8-105). Shown.

33 201226394 40550pif

s 34 201226394 jvjjif

35 201226394 40550pif

36 201226394 40550pif

37 201226394 40550pif

38 201226394

39 201226394 40550pif

40 201226394 40550pif

41 201226394 40550pif

<Specific example of the compound represented by the formula (1-9)> The compound represented by the formula (1-9) is specifically represented by the following formula: (^948). Among these, preferred compounds are of the formula (1_9_~(1-9-12), (1-9-16)~(1-9-18), and the formula (1-9-34)~(1 g ; And (1-9-40)~(19-42). - ·36) 42 201226394 40550pif

(1-9-9)

43 201226394

201226394 40550pif

(1-9-25)

(1-9-26)

(1-9-28) (1-9-27)

(1-9-29) (1-9-30)

(1-9-32) (1-9-31)

(1-9-33) 45 201226394 40550pif

(1-9-35) (1-9-37) (1-9-39)

(1-9-41)

46 201226394 ^fU^DUpif <Specific Example of Compound represented by Formula (1-10)> Specific examples of the compound represented by Formula (1-10) are, for example, the following formula (1-10-1) to (1- 10-48) shown. Among these, preferred compounds are the formulae (1-10-1) to (1-10-6), (1-10-10) to (1-10-12) and (1-10-16)~ (1-10-21).

47 201226394 'tvjjjupif

(1-10-10) (1-10-12) (1-10-14) (1-10-18) (1-10-21) (1-10-16)

(1-10-19)

(1-10-23)

48 201226394 40550pif

(1-10-26) (1-10-28) (1-10-30) (1-10-32) 49 201226394 40550pif

50 201226394 40550pif <Specific example of the compound represented by the formula (1-11)> Specific examples of the compound represented by the formula (1-11) are, for example, the following formula (1-11-1) to (1-11-60) ) shown. Among these, preferred compounds are the formulae (1-11-3) to (1-11-10), (1-11-25) to (1-11-28) and (1-11-51)~ (1-11-60).

51 201226394 40550pif

52 s 20122639 seven

(1-11-35) (1-11-37)

53 201226394 40550pif

54 201226394 40550pif

<Specific Example of the Compound of the Formula (M2)> Specific examples of the compound represented by the formula (1-12) are shown by the following formula (1-12-1) to (1-12-60). 55 201226394 4U55Upif

(1-12-1)

(1-12-2) (1-12-3) (1-12-5) (1-12-7) (1-12-9)

(1-12-6) (1-12-8) (1-12-10) (1-12-4) s 56 201226394t • ^ L·^ ίί.

(1-12-12) (1-12-11)

(1-12-14) (1-12-16) (1-12-18)

(1-12-20)

j j (1-12-22)

(1-12-23)

丫, (1-12-24) s 57 201226394 40550pif

(1-12-25)

(1-12-26) (1-12-27)

(1-12-33) (1-12-31)

(1-12-34)

(1-12-35)

(1-12-37)

NT 58 s 201226394 40550pif

(1-12-41)

(1-12-40) (1-12-42) (1-12-43)

(1-12-47) (1-12-49) (1-12-45)

(1-12-48) (1-12-50)

59 201226394 40550pif

<Specific example of the compound represented by the formula (1-13)> Specific examples of the compound represented by the formula (1-13) are shown by the following formula (1-13-1) to (1-13-60). . Among these, preferred compounds are the formulae (1-13-21) to (1-13-28) and the formula (1-13-31) to (1-31-40). 201226394 40550pif

(1-13-2) (1-13-4) (1-13-6)

6 61 201226394 40550pif

62 201226394 40550pif

63 201226394

S 64 201226394 ^fu^^upif

<Specific example of the compound represented by the formula (1-14)> Specific examples of the compound represented by the formula (1-14) are shown by the following formula (1-14-1) to (1-14-60). . Among these, preferred compounds are the formulae (1-14-1) to (1-14-18). 65 201226394 40550pif

66 201226394 40550pif

67 201226394

68 201226394 40550pif

69 201226394 40550pif

<Specific Example of the Compound of the Formula (1-15)> The specific formula of the compound represented by the formula (M5) is, for example, the following formula (1-15-1) to (1-15-48). Among these, preferred compounds are the formulas (1-15-10) to (1-15-12), (1-15-16) to (1-15-18), and the formula (1-15-34). ~ (1-15-36) and (1-15-40) ~ (1-15-42). 201226394 40550pif (1-15-2)

(1-15-8) (1-15-9) 71 201226394 40550pif

201226394

(1-15-29) (1-15-30)

73 201226394 *u

<Specific Example of Compound represented by Formula (1-16)> Specific examples of the compound represented by Formula (1-16) are shown by the following formula (1-16-1) to (1-16-24) . Among these, preferred compounds are the formulae (1-16-1) to (1-16-5).

S 74 201226394 40550pif

(1-16-1) (1-16-3) (1-16-5) (1-16-7) (1-16-9)

(1-16-2) (1-16-4) (1-16-6) (1-16-8) 75 201226394 40550pif

s 76 201226394t <Synthesis method of compound> A method for synthesizing the compound of the present invention will be described by F '. The compounds of the present invention can be synthesized by a suitable combination using a general known synthetic method. . <Synthesis of a compound represented by the formula (1-7-1) to the formula (1-7-144)> Reaction 1

m : an integer of 1 to 5 First, a 9-phenyl onion substituted with an alkyl group (cycloalkyl group) is synthesized by the reaction 1. The alkyl-substituted bromobenzene is reacted with magnesium metal in THF to prepare a Grignard reagent, which is reacted with 9-bromoindole in the presence of a catalyst to form a phenyl group through an alkyl group (ring). Alkyl) substituted 9-phenylindole. The combination of the benzene ring and the anthracene ring is not limited to the above method. For example, a root-shore coupling reaction using a zinc complex or a Suzuki coupling reaction using boric acid or a boric acid ester may be employed, and these conventional methods may be suitably used depending on the situation. 77 201226394 HUO^Upif Reaction 2

Reaction 2 is a bromination at the 10-position of 9-phenylindole substituted with an alkyl group (cycloalkyl) using N-bromosuccinimide. Here, a common brominating agent other than the amber succinimide can also be used.

Reaction 3 is the coupling of an anthracene ring to a naphthalene ring. Firstly, 2_ bromo-6-methoxynaphthalene is prepared into a Grignard reagent according to a conventional method, and reacted with a 9-bromoindole derivative synthesized in the reaction 2 in the presence of a catalyst to synthesize 9_(6-methoxy group). Naphthalene-2-yl)-10-phenylindole derivative. In the same manner as the reaction oxime, the benzene ring and the oxime ring are not limited to the above; for example, a root-shore coupling reaction using a rhodium complex or a Suzuki coupling reaction using boric acid or a boric acid ester can be used. It is appropriate to use these conventional methods.

78 201226394 -IT 丄 1

Reaction 4 is a dehydration group of a 9-(6-methoxynaphthalen-2-yl)-10-phenylindole derivative to form a naphthol. Here, a reagent which is commonly used for the demethylation reaction can also be suitably used. Reaction 5

Reaction 5 is the conversion of the -OH of naphthol to triflate. -OTf in the reaction formula is an abbreviation of -OS02CF3. Reaction 6

Br · HCI i-PrMgCl i-PrMgCl

ZnCl2 · TMEDA

THF

Reaction 6 was carried out by a Negishi coupling reaction to bind a naphthalene ring to a bite 79 201226394 40550 pif ring. First, 4_bromopyrazine is sprayed because it is a salt which is stable to the raw material. Here, 'Mer's isopropyl gasification money, but it doesn't matter if you don't have to use 2 times. To the Grignard reagent, a bis:ethylamine complex is added, and a zinc hydride complex of t-form is synthesized, and the target is obtained by reacting with trifluoroethylene obtained in the reaction 5. In addition to the root-coupling reaction, the reaction 6 may suitably employ a conventional coupling reaction such as a Suzuki coupling reaction. In the case of using Suzuki coupling reaction, the most suitable boric acid or boric acid ester can be prepared according to the target. For example, a boric acid ester represented by the following reaction 7 can be used to obtain a target product. Reaction 7

Specific examples of the palladium catalyst used for the coupling reaction include Pd(PPh3)4, PdCl2(PPh3)2, Pd(OAc)2, and tris(dibenzylideneacetone) 2 201226394 40550pif satiety (〇), Tris(dibenzylideneacetone)dipalladium (yttrium) chloroform complex, bis(diphenylideneacetone)palladium (ruthenium), bis(tri-t-butylphosphino)palladium (ruthenium), or (1, Γ_bis(diphenylphosphino)ferrocene) digas palladium (II). Further, in order to promote the reaction, a phosphine compound may be added to the phenol compounds as the case may be. Specific examples of the phosphine compound include tris(t-butyl)phosphine, tricyclohexylphosphine, and 1-(N,n-dimethylaminomethyl)_2-(di-t-butylphosphino)di Ferrocene, 1 _(N,N-dibutylaminomethyl)_2_(di-t-butylphosphino)ferrocene, 1-(methoxymethyl)-2-(di-t-butyl Phosphyl)ferrocene, U'-bis(di-t-butylphosphino)ferrocene, 2,2,_bis(di-t-butylphosphino)-ι,ι,-binaphthyl, 2_ Methoxy 2'-(di-t-butylphosphino) naphthalene, or 2·dicyclohexylphosphino-2',6,-dimethoxybiphenyl. Specific examples of the base to be used in the reaction include sodium carbonate, potassium carbonate, carbonic acid planer, sodium hydrogencarbonate, sodium hydroxide, potassium hydroxide, hydrogen oxygen = hydrazine, sodium ethoxide, sodium butoxide, sodium acetate. , tripotassium phosphate, or potassium fluoride. Further, specific examples of the solvent to be used in the reaction include stupid, indene, xylene, 1,2,4-trimercaptobenzene, anthracene, fluorene-dimethylformamide, tetrahydrofuran, and diethyl. Ether, tert-butyl methyl ether, hydrazine, 4-dioxane, methanol, ethanol, cyclopentyl methyl ether or isopropanol. These solvents may be appropriately selected and used singly or as a mixed solvent. <Method for Combining Compounds Represented by Formula (1-8-1) to Formula (1-8-105)&gt; In the above Reaction 3, 'If 2-bromo-7-methoxynaphthalene is used instead of 2-bromo The oxynaphthalene can be synthesized in the same manner. <Formula (1-9-1) to Formula (1-9-48) and Formula (l-io)) to Formula (11〇48) 201226394 Method for synthesizing the compound represented by 4U55Upif&gt; By using such benzene The raw material substituted with the skeleton and the naphthalene skeleton may be used in the same manner as described above instead of the raw materials used in the above Reactions 1 to 3. That is, 'the 2-Bromopurine Grenner reagent is coupled with 9-bromoindole, and according to the reaction 2, the onion is ^(10)', then the precursor is tested with the lattice of the f-oxygen or m-methoxy group and the silk. And 9_(4_ or 3•methoxyphenyl)-10-(2-naphthyl)anthracene is obtained. The order after the demethylation reaction of the compound 'oximeoxy group' may be carried out in accordance with the above. Further, in addition to the specifically exemplified compound, it is of course possible to carry out the synthesis according to the above synthesis method by suitably using a raw material according to the target. <Formula (1-11-1) to Formula (M1_60), Formula (M2)) to Formula (1-12_60), Formula (1-13-1) to Formula (1-13-60), and Formula (i- 14-l) Synthesis method of the compound represented by the formula (1-10-60)&gt; by using an alkyl group or a cycloalkyl-substituted pyridine derivative instead of the raw material used in the above reaction 6 or reaction 7 The pyridyl derivative can be synthesized in the same manner as described above. The pyridine derivative substituted with a decyl group or a cycloalkyl group can be synthesized as shown in the following Reaction 8 to Reaction 9. Here, the formula (1) is exemplified. 11-11) A method for synthesizing a pyridine moiety in a compound represented by the formula (1-12-11), the formula (M311), and the formula (M4-11), but various calcinations can be synthesized by appropriately changing a raw material. Or a cycloalkyl substituted η than a sigma derivative.

82 201226394 40550pif Reaction 8 Br

Reaction 9

1) RLi or Mg or RMgX2) ZnCI2 or ZnCI2.TMEDA

Cizn-〇-

Br

Pd-catalyst

&lt;Formula (1-15-1) to Formula (1-15-48) and Formula (Bu 16-1) to Formula (1-16-24), the method for synthesizing the compound &gt; In the step of introducing a phenyl group in the method for synthesizing a compound represented by the formula (1-9-1) to the formula (1-9-48) and the formula (1-10-1) to the formula (M0-48), A phenyl group substituted with an alkyl group or a cycloalkyl group may be used. For example, the synthesis method shown in the following reaction 10 can be used. Reaction 1 〇

The definition of R in the formula is the same as described above. 〇 is an integer from 1 to 4. According to the target compound, only the required amount of Han is linked at any position of the benzene ring. In the case where the compound of the present invention is used for a layer of a germanium layer or an electron transport layer in an organic EL device, the application of the electric field turtle _ / in indicates that the compound of the present invention is used as an electroluminescent element, Sub 2:: 83 201226394 Excellent for 4U^5Upif materials or electron transport materials. Here, the layer of the electron injecting unit; the so-called electron transfer _ is used to transport the electrons of the host to the layer 1 of the light-emitting layer, and the electron transport layer is injected into the layer. The materials used for each layer are referred to as electron injecting materials and electron transporting materials. &lt;Description of Organic EL Element&gt; 2 The invention is an organic EL element of a compound represented by the formula (1) which is contained in an electron injecting layer or an electron transporting layer. The organic EL device of the present invention has a low driving voltage and high durability at the time of driving. The organic EL device of the present invention has various (four) structures, and is basically a multilayer structure in which at least a hole transport layer, a light-emitting layer, and an electron transport layer are sandwiched between a saint and a cathode. Examples of specific components of the component are: (1) anode/same transmission layer/light-emitting layer/electron transport layer/cathode, (1) anode/hole injection/electrical transmission layer/light-emitting layer/electron transport layer/cathode, (3) Anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode, and the like. The compound of the present month has two electron injecting properties and electron transports, so that it is used alone or in combination with other materials for the electron injecting layer or the electron transporting layer. The organic EL device of the present invention can also obtain blue, green, red or white light by using a hole injection layer, a hole transport layer, a light layer or the like of other materials in combination with the electron transport material of the present invention. The luminescent material or luminescent dopant which can be used in the organic EL device of the present invention is: S molecular engineering, polymer functional material (4) "Photonic material f co-published (1991), p236, the daylight fluorescent material , fluorescent brightener, laser pigment, organic scintillator, various kinds of firefly

84 201226394 40550pif Luminescent materials such as photo-analytical reagents, etc., edited by the CMC Society, edited by the CMC, "organic rainbow materials", (10) 1) the materials described in pi55 to 156, and the luminescent materials of the triplet materials described in P170 to 172. . Compounds which can be used as luminescent materials or luminescent dopants are: polyaromatic compounds, heterocyclic aromatic compounds, organometallic complexes, color=molecular secret materials, styryl derivatives, (tetra) amine derivatives , a derivative, a derivative, and. (4) Derivatives, with the formation of spiro rings, evil organisms, riding creatures, etc. Polycyclic aromatic compounds, bismuth, bis, phenanthrene derivatives, fine benzene emitters, silk organisms, organisms, strontium derivatives, red fluorene derivatives, and the like. Fragrant incense _ sub-: is a di-silyl or diarylamine: 嗔 余 生物 生物 、 、 、 生物 生物 生物 生物 、 、 、 ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ Matter, styrofoam with triphenyl η group, Shiyan fascinating object, etc. Organic metal mismatch = example two words, Ming, 铍, pin, test, steel, silver, turn, iron, gold-based clock derivative, An example of a benzene-reading organism, a benzoate derivative, a ri° street-native n-derivative, a benzo-imiding organism, a derivative 2, a deuterated derivative, a morphine derivative, etc. · 咕 ( 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬 酬Derivatives, quinar-derived 2 ί derivatives, stupid derivatives, benzoic acid derivatives, benzoic acid, etc. Examples of polymer-based luminescent materials are: poly(p-phenylene), biosynthesis Phenanthene derivatives, polyethylene scent (tetra) derivatives, polylith eve 85 201226394 40550pif alkane derivatives, poly derivatives, polyparaphenyl derivatives, etc. Styryl derivatives Examples are: an amine-containing styryl derivative, a styryl aryl derivative, etc. The other electron transporting material used in the organic EL device of the present invention can be used as a compound which can be used as an electron transporting compound in a photoconductive material. It can be used as an electron transport layer of an organic EL element and a compound of a ferrite layer. Specific examples of such an electron transport material are: a ruthenium-based metal complex...bipyrene, anthracene derivative, phenanthroline Derivatives, biphenyl hydrazine derivatives, abominable sitting organisms, porphin derivatives, tri-sit derivatives, bismuth, and metal complexes of base derivatives, (4) lin derivative: wow = Derivatives of polymers, compounds, gallium complexes, phenylenes, triazine derivatives, pyridazine derivatives, υ'τ bio, imipenem derivatives, derivatives, etc. Hole injection material and hole injection material used for organic EL element: from the previous charge in the photoconductive material as a hole == compound, or hole injection layer of organic el element The second is to make: two people: any choice of materials The use of biological, etc.. The material of the living organism, the triarylamine derivative, and the phthalocyanine derivative layer can be formed by the respective constituents of the composition. The properties of the film material can be formed by the formation method or the like. It is suitable to form a film; it is not particularly limited, and may be in the range of 2 nm to 5 〇〇〇 nm according to the enthalpy. 86 201226394 40550pif In addition, the method of the luminescent material film (four) is preferably _ because it is easy to obtain a homogeneous Membrane, and it is not easy to generate pinholes/. In the case of thinning using the electroplating method, the steaming condition is different according to the invention, and the type of the photomaterial* is not (5). Generally, it is preferably set in the following range: the temperature of the heating boat is 耽~gamma^, the degree of vacuum is 10.6 Pa~10-3 Pa, and the speed of steaming is 〇01 nm/sec~5 〇 fine, ς ^ substrate The temperature is -150 ° C to +30 CTC, and the film thickness is 5 ηιη to 5 μιη. The organic EL device of the present invention is preferably supported by any of the above structures. As long as the substrate has mechanical strength, thermal stability, and transparency, a glass, a transparent plastic film, or the like can be used. For the anode material, it is possible to use the alloys Sn02 and z, which are CUI indium tin oxides (hereinafter, the 'smooth cathode material can use a metal having a work function of less than 4 ev, a compound = a compound, and a mixture thereof. Specific examples thereof are H弼, town, , alloys, alloys, etc. alloys, / bell, magnesium / silver, magnesium / indium, etc. In order to efficiently extract some of the light, it is desirable to at least one full reduction of the organic EL read as The sheet resistance electrode of the electrode has a permeability of 10% or more. It is a property of the electrode material, but is usually set in the range of 10 = 2 = 2 nm. Such an electrode can be used by evaporation or ruthenium by using the above. The method of forming a thin enamel by money, etc. is made of: - ί / 吏 二 tt Ming qiaoqiao material to make the organic EL element 3 above the dangerous pole / hole injection layer / hole transmission 87 201226394 The electron transport material of the present invention The thin material of the cathode/organic EL element is formed on the appropriate substrate by a vapor-deposited hole to form a hole injection layer and a positive electrode on the impurity electrode. A film on which the light-emitting layer is formed is formed. An electron transporting material invented on the light-emitting layer is formed into a film By electroporation, a thin film containing a substance for a cathode is formed by steaming, thereby obtaining a target organic EL element. Further, in the above-described production of the Lit member, the order of fabrication can be reversed, and the cathode can be sequentially fabricated. In the case where a DC voltage is applied to the organic EL element obtained as described above, the light is applied to the organic EL element obtained in this way, and the voltage is applied to the polarity of the anode and the polarity of the cathode is -, if 2 V is applied. When the voltage is about 40 V, the light can be observed from the transparent or translucent electrode side (anode, cathode, and both), and the organic EL element emits light even when an alternating voltage is applied. The waveform of the alternating current can be arbitrary. [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 below. [Synthesis Example 1] Synthesis of Compound (1-7-74) &lt;Synthesis of 9-(4-t-butylphenyl)anthracene> Under a nitrogen atmosphere, 31 g of 9-bromoindole, 25 g of 4-tert-butylphenylboronic acid, and Pd (PPh3) were added. 41.3 g, potassium phosphate 51 g and 1,2,4-trimethylbenzene 150 The flask of ml was stirred at reflux temperature for 21 hours. The reaction solution was cooled to 201226394 40550 pif but was taken to room temperature and then water was added _separation. Separation by liquid extraction (hqmd solid, washing with decyl alcohol, and washing with a third butyl benzene fine 28 g (tetra) acid S S which is precipitated by reading the solvent to obtain 9 gram of &lt;9_ desert -1 is the synthesis of the third phenyl group) & Added 9-(4-tert-butyl phenyl 3 〇〇 ml S, 19 g. Stir at room temperature 丨n± ^ n戌坭j Since the 酝月月女1* /5 /3⁄4.# ', 夺, add sodium thiosulfate aqueous solution and stop the reaction mixture to transfer to the liquid separation funnel, using the imitation to extract. Borrow * suction set!饤f, followed by steam reduction from the gas _ (four) solid, and then recrystallized from the sputum to obtain phenyl) 蒽 29 g. , Le Yi &lt;Synthesis of 3-(6-bromonaphthalen-2-yl)pyridine&gt; The flasks of "smelly i 〇g and THF 6 () ml were cooled in an ice bath, in a secret environment, - side The lion - while adding isopropyl chloride chlorinated THF solution 35 m after the completion of the dropwise addition, temporarily warmed to room temperature, cooled in ice water, while adding secret zinc - tetramethyl ethanediamine The complex I7g. Afterwards, at room temperature _H, after the addition of trisole: acid 6-bromonaphthyl ester 18 g and PdCl2 (dppp) 1.6 g, was scrambled for 3 hours at reflux temperature. After the reaction liquid is cooled to room temperature, in order to remove the metal ions of the catalyst, an ethylenediaminetetraacetic acid/tetraammine salt dihydrate which is equivalent to about 3 times the molar amount of the target compound is added and dissolved in an appropriate amount of water. The solution (hereinafter, abbreviated as EDTA · 4Na aqueous solution) and toluene were separated by liquid. After distilling off the solvent under reduced pressure, the column was chromatographed by ruthenium column chromatography (曱89 201226394本/乙乙格为=7/3 base) Pyridine 12 g. (Production ratio)) Purification to obtain 3·(6-bromonaphthalene_2_<compound of compound (1-7々4)> 3-Γ6′, self-poor 1 5.9 s, 雔Bu wu _2 · · 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 6.2 The flask was placed under nitrogen for a period of 4 hours. To the solution, 9_Mo·1〇-(4_Second native)蒽8.6 g, potassium phosphate 9.3 g and 1,2,4-triazole were added to the solution. Benzene 50" using Didike tube to heat the dimethoxyethyl wire at room temperature, add 2 ml of second butanol, 5 m of water (di-mercaptoacetone), 0.4 g and 2 g of hexyl sulphate 5 g, further mixing at reflux temperature for 2 hours. The mixture was cooled (4) at room temperature, and after washing with water, the solid was collected by suction filtration. The obtained solid was washed with decyl alcohol, washed with ethyl acetate, and purified by hydrazine column chromatography (benzene/ethyl acetate = 9/1 (volume ratio)) to obtain a compound (hm). ): 3-(6-(1〇-(4_t-butyl)phenyl)indoleyl)naphthalene-2-ylpyridinium g. The structure of the compound was confirmed by NMR measurement. ^-NMR (CDC13): δ = 9.07 (m, lH), 8.68 (dd, lH), 8.23 (m, lH), 8.15 (d, lH), 8.08 (m, lH), 8.03 (m, 2H) , 7.83 (dd, lH), 7.78 (d, 2H), 7.72 (d, 2H), 7.68 (dd, lH), 7.63 (d, 2H), 7.42-7.48 (m, 3H), 7.30-7.38 (m , 4H), 1.49 (s, 9H). [Synthesis Example 2] Synthesis of Compound (1-7-26) &lt;Synthesis of 9-(3-Tolyl)purine&gt; 201226394 Under the environment of 40550pif, 9 g of onion 36 g, 3-methylbenzene was added Base shed II i, PPh3) 41 4g4_ 59 § and 丨, 2, 4 ^ · methyl benzene 150 at reflux temperature _ 2 5 hours. The test is cooled to the chamber to distill off the benzene to perform liquid separation. After purifying the medium = insect toluene solution using a short-slurry hose column, the solvent was removed under reduced pressure. The oil t obtained was added to the obtained oil t, and the precipitated solid was collected by aspiration to obtain a synthesis of 9 minutes of benzophenone 31 g 〇 &lt;9-bromo-10_(3_ phenylphenyl) hydrazine. 9-(3-Phenylphenyl)蒽3〇§ and in a 2〇〇mi flask in the 'online environment in the ice crunch, add _ hu ship imino moth ^ 1 §. At a temperature of -15 hours, the reaction was stopped by adding sodium thiosulfate solution. The solution was transferred to a liquid separation funnel, and the == inspection tube (4) was taken after extraction. The ship was added under reduced pressure to remove the solution obtained by the solution, and the precipitated solid was sucked to obtain 9-di-10-(3-indolyl) 蒽3〇 g. &lt;Synthesis of 4,4,5,5-tetradecyl-2-(10-(3_曱 基)) Onion Η Η 二 Dioxopentane Ring&gt; 9 备10-(3 _tolyl)g 3〇g, conjugated acid vinegar vinegar g, bis(diphenylidene acetonide) put (〇) i 5 g, tricyclohexylphosphine] 4 g, acid clock 15 g, potassium carbonate 12 g and cyclopentyl hydrazine _ 1 〇〇 ml flask = gas environment, under the degree of return _ 1M, when the limb solution is cooled to warm, add water and toluene for liquid separation, using a short 矽 rubber column The obtained toluene solution was purified, the solvent was distilled off under reduced pressure, and heptane was added to the obtained oil, and the precipitated solid was collected by suction filtration to obtain 4,4,5,5·91 201226394 40550 pif g. A (1G (3. Abenyl) S,9·yl)-1,3,2·diqi_pentane μ <Compound (1, synthesis &gt; 4 4 s &lt;^2.^1; : Ψ &amp; -2-(1〇-(3- ^ ^ ) t -9-

Pd (PPh3M &quot; gg W 酉夂 potassium 13 Π 2, 4 _ tridecyl alum, such as, butyl, m and water 1 〇mi flask was mixed at reflux temperature = should be liquid cold after teaching room temperature, add water and T benzene The liquid separation is carried out, and the obtained crude product is purified by Na-column chromatography (toluene/acetic acid ethylbenzene 201 =)), and then recrystallized from toluene fraction and hydrazine to obtain a compound i: tolyl group蒽-9-yl)naphthyl) „比—7 , #丄^ (1〇-(3- structure of the compound. (Chemical error confirmed by NMR to confirm HNMR (CDC13): 5 = 9.06 (m, lH ), 8.67 (dd, lH) 8.22 m 1=, 8.14 (d, 1H), 8 〇 6 (m, ' ' 7.81 (m, lH), 7.75 (d, 2H), 77,, 7.50 (t, lH) ), 7.45 (m, 1H), 72,;, 7. (5), 1H), [Synthesis Example (10) 987-) 7.=/H), 2.5 hearts &lt;9-(3-tert-butylbenzene Synthetic port of onion) &gt; In a nitrogen atmosphere, 9-bromoindole phenyl)_4,4,5,5-tetramethyl], 3,2-dioxa'^ 3.1 g, potassium phosphate was added. 37g, l,2,4-triterpene is lean, the flasks of g ( Ph3) 4 and water 3 (iv) are at reflux temperature; after the third butanol is compiled to room temperature, water and stupid are added; Cold set liquid separation Using short silicone tubes

92 S 201226394 40550pif The f-benzene solution of (iv) was reduced in weight to remove the solvent, and 9-(3-t-butylphenyl) 4 24 g was obtained by sucking 9 a solid precipitated by adding methanol. &lt;9-&gt;Synthesis of odor-1 〇_(3_t-butylphenyl)anthracene&gt;

To the addition of 23 g of 9-(3-t-butylphenyl)anthracene, iodine O.lg and THF 0, the flask was stirred in a nitrogen atmosphere, and N-glycol was added to the yttrium I. The reaction was stopped by adding an aqueous sodium thiosulfate solution. The solution was transferred to a liquid separation funnel and extracted with toluene. !!=石夕胶: The toluene solution obtained by column purification 'removal of digan' under reduced pressure, and then reprecipitated by hydrazine/sterol to obtain 9 g of 10_(3_t-butyl-based) onion 23 g . <Synthesis of Compound (1-7-98)> Addition of 3-(6-&gt; Odornaphthalene_2_base to bite 6.2 g, chlorpyrifos pinacol 7 f, double ( Two subunits, propylene, argon, argon, arsenic, arsenic, arsenic, arsenic, arsenic, arsenic, arsenic, argon The dish is won for 4 hours. To the solution, 9 〇 1 〇 (3_2Λ 苯基 phenyl) onion 8·6 8 , potassium citrate 9·3 g and 1,2,4·trimethylbenzene are added to the solution. 5 迪Den-Stark tube, dimethoxyethyl wire often, 5, water 5ml, bis (dipyridyl propyl hydrazine), 'g and one% hexylphosphine 〇 · 5 g, in After further stirring at reflux temperature, the reaction solution is cooled to room temperature, washed with water to dissolve the salt, and then purified by a mixture of the wrong body, gel column chromatography (benzene/acetic acid ethyl acetate 曰^tb). After obtaining the solid, 'repeating from toluene--obtaining compound (1々8): 3_(6__•third τ-phenyl) 93 201226394 蒽-9-yl)naphthalen-2-yl). 1.5 g. The structure of the compound was confirmed by NMR measurement. !H-NMR (CDC13) : δ = 9.07 (m, lH) , 8.68 (dd, lH), 8.23 (s, lH) , 8.16 (d, lH) , 8.08 (m, lH) , 8.03 (m, 2H) ), 7.83 (m, lH), 7.75 (d, 2H), 7.72 (d, 2H), 7.68 (m, lH), 7.52-7.61 (m, 3H), 7.46 (m, lH), 7.30-7.38 ( m, 5H), 1.41 (s, 9H) 〇 [Synthesis Example 4] Synthesis of Compound (1-7-96) &lt; 2-(10-(4-T-butylphenyl)fluoren-9-yl) Synthesis of _4,4,5,5-tetramethyl-1,3,2-dioxaborolane> 9-bromo-10-(4-t-butylphenyl)phosphonium 7.8 g, 6.1 g of pinacol borate, bis(dibenzylideneacetone)palladium(0) 0.3 g, tricyclohexylphosphine 〇.3 g, potassium acetate 39 g, potassium carbonate 2.8 g, and cyclopentyl methyl ether The 4 C ml flask was stirred at reflux temperature for 6 5 hours under a nitrogen atmosphere. After the solution is cooled to room temperature, water and benzene are added for liquid separation and decompression. Add heptane to the obtained oil, and collect tetrahydropyrene 1 3 2 to obtain Γ 2 for (4-t-butylphenyl) sulfonyl)_4,4,5,5·methyl- by suction filtration. 1,3,2· Dioxolane pentane 6 9g. The second synthesis > THF2 〇 ml flask in ^, = M3 · silk base) such as 9.8 g and dropwise addition of 2.6M n-butyl kiln methanol bath to cool -70X: below, slowly mix for 0.5 hours, add gasification 丨7 After completion of the dropwise addition of 111, the mixture was stirred at room temperature for 5 hours at room temperature, and 12 g of tetradecylethylenediamine complex. After that, talk about 'Tega bromine naphthalene 2 - ester 15

S 201226394 40550pif ^ C-bar (〇) and bis(diphenylphosphino)-propanone · 5 g, the secret time of the recovery. After completion of the reaction, add edta · hydrazine f night, ethyl acetate for liquid separation, and distill off the solvent under reduced pressure, 'It is by active oxygen her f column chromatography* (f benzene / acetic acid vinegar = 9 / 1 (volume More than)) to carry out purification. Then, it was washed with methanol, and mixed with acetic acid/methanol to dissolve the crystal, and Weng 4_(3_(6_钱_2乂phenyl) 0 was 5.3 g. <Compound (1-7- Synthesis of 96) will be added with 2-(1〇-(4-t-butylphenyl)phosphonium-9-yl)-4,4,5,5-tetramethyl-1,3,2- Dioxaborolane 6.1 g, 4-(3-(6-bromonaphthalen-2-yl)phenyl)pyridinium 5.0 g, Pd(PPh3) 40.5 g, potassium carbonate 3.0 g, 1,2,4- The flask containing 25 ml of triterpene, 5 ml of tributanol and 5 ml of water was stirred at reflux temperature for 6 hours. After cooling the reaction solution to room temperature, EDTA·Na water and hydrazine were added for liquid separation and decompression. The solvent was distilled off, and the obtained crude product was purified by active alumina column chromatography (benzene/ethyl acetate = 9/1 (volume ratio)). After washing with solid, recrystallization from benzene to give compound (1-7-96): 4 (3-(6-(10-(4-t-butylphenyl)fluoren-9-yl)naphthalene 2-yl)phenyl). 3.3 g of pyridine. The structure of the compound was confirmed by NMR. ^-NMR (CDC13): 8.73 (dd, 2H), 8.27 (m, lH), 8.15 (d, lH) ), 8.03 (m, 3H), 7.99 (m, 2H), 7.78 (d, 2H), 7.73 (d, 2H), 7.61-7.70 (m, 7H), 7.44 (m, 2H), 7.30~7.38 (m , 4H), 1.49 (s, 9H) [Synthesis Example 5] Synthesis of Compound (1-14-14) 95 201226394 40550pif &lt;9-(3-ethoxyphenyl)_1Q_(naphthalene-2-yl)anthracene Synthesis> Add 1 spring 3-ethoxybenzene 72 4 g, (10_(naphthalene-2-yl)phosphonium-9-yl)boronic acid 104.5 g, Pd(pph3)4 1〇4 g, phosphoric acid Potassium 127 4 g, 1,2,4-trimethylbenzene 600 ml, 2-internal alcohol 12 〇m b and water 12 〇m b in the nitrogen ring U 'at reflux temperature _ M, time. To the chamber &gt; after the dish 'by washing the solid in the collection liquid, washing with decyl alcohol to obtain ethoxyphenyl)-10-(naphthalen-2-yl) fluorene 82 §. &lt; 3-(10-(naphthalene-2-yl)phosphonium-9-yl) stupid_synthesis> Add 9♦ ethoxyphenyl)_1〇·(naphthalen-2-yl)fluorene 82 and ° to the flask Than ._ 446.G g 'money gas environment, stirring at reflux temperature = time. After cooling the reaction solution to room temperature, water was added to absorb the precipitated solid H, washed with methanol, and washed with benzene to obtain 3-(10-(qin-2-yl)indole-9. ) Benzene age 〇g. 〉&lt;Trifluoromethane-3. (Cai-2-yl) 蒽冬基) The synthesis of benzene vinegar will be added with 3 (naphthalene·2^9_yl) (10) (g) and 吼疋-W The riser tile is cooled in an ice bath, and in an airy environment, it is dropped into the acid liver 65.0 g. After the addition is completed, further disturb the benzene vinegar at room temperature 9 (^ g. 'Pay the two chaotic smoldering acid 3_(10•(naphthalene-2-yl) onion winter base) Α) 1<3 Γ:5 :5-Tetramethyl-2 (1〇-(naphthalene-2-yl) onion-based) phenylhydrazine)-1,3,2--oxaborolane synthesis &gt; Add to: Trifluoromethane 3_(1〇_(Cai_2) onion) 96 201226394 40550pif phenyl ester 90.3 g, boranoic acid pinacol ester 521 g, bis(dibenzylideneacetone) palladium (〇) 7.4 g, 7 2 g of tricyclohexylphosphine, 33 6 g of potassium acetate, 23.6 g of potassium carbonate, and 5 〇〇ml of phenyl hydrazine, and stirred at reflux temperature for 5 hours. After cooling the reaction solution to room temperature, the insoluble matter was removed by suction filtration using a Kiriyama funnel coated with diatomaceous earth, and the filtrate was washed with EDTA · 4Na water. The solid obtained by distilling off the solvent of the filtrate under reduced pressure was washed with Geng Hyun to obtain 4,4,5,5-tetradecyl-2-(3_(10-(naphthalene-2-yl)fluoren-9-yl) Phenyl) '3 2: oxaborolane (52.0 g). '&lt;Synthesis of Compound (1-14-14)> To the flask was added 4,4,5,5-tetradecyl-2-(3-(10-(naphthalen-2-yl)indole_9_yl) 5,_bromomethyl-2,2,bipyridyl 11 which is synthesized by the method described in JP-A-2009-124114. 5.1 g, Pd(PPh3)4〇.6 g, potassium 7.2 g, 1,2,4-trimethylbenzene 25 ml, third butanol 5 ml, and water 1 ml, mix at reflux temperature 2.5 hours. After the reaction solution was cooled to room temperature, water was added, and the solid in the collected liquid was collected by suction filtration, and washed with decyl alcohol. The solid was purified by ruthenium column chromatography (benzene/ethyl acetate 2/1 (volume ratio)) and then further purified by activated carbon column chromatography. The solution is concentrated and recrystallized from chlorobenzene to obtain the compound (1-14-14): 3-mercapto-5,-(3-(10-(naphthalen-2-yl)fluoren-9-yl)phenyl )-2,2'-bipyridyl 2.3 g. The structure of the compound was confirmed by NMR measurement. 'H-NMRC CDC13) : 6 = 9.05 ( m,lH) , 8.55 ( d,lH) , 8.11 (dd,lH), 8.09( d,lH), 8.02( m,lH), 8.00( s,lH) , 7.73-7.95 (m, 9H), 7.60 (m, 5H), 7.30-7.40 (m, 4H), 7.23 (m, lH), 97 201226394 2.56 (s, 3H). [Synthesis Example 6] Synthesis of Compound (1-11-1) &lt;Synthesis of 2-Mercapto-4-(6-(10-phenyl onion-9-yl)naphthalene-2-yl)pyridine> 4 ,4,5,5-tetradecyl-2-(6-(10-phenylindole-9)naphthalene-2-yl)-1,3,2-dioxaborolan (2.0 g), 4-bromo-2-indenylpyridine (0 8 g), Pd(PPh3) 4 (0.3 g), acid lf (1.7 g), 1,2,4-trimethylbenzene (2〇mi), Third butanol (5 ml) and water (1 ml) were added to the flask, and the mixture was stirred at reflux temperature for 7.5 hours under a nitrogen atmosphere. After the completion of the heating, the reaction solution was cooled to room temperature, and water and toluene were added to carry out liquid separation. The obtained solid was purified by vacuum distillation to remove &gt;granules&apos; by chromatography on silica gel column chromatography (developing solvent: benzene/ethyl acetate = 95/5). Next, the obtained eluate was passed through a short activated carbon tube column to remove the coloring component. The crystals precipitated during the removal of the obtained filtrate were collected under reduced pressure to obtain the compound 2-methyl-4-(6-(10-phenylfluoren-9-yl) represented by (1-11-1). Cai-2-yl) B is determined by σ (〇.7g). The structure of the compound was confirmed by NMR measurement. ^-NMR (CDC13): δ = 8.66 (d, lH), 8.30 (S, 1H), 8.17 (d, lH), 8.03 (m, 2H), 7.87 (d, lH), 7.72-7.78 (m, 4H), 7.70 (d, lH), 7.65 (m, 2H), 7.58 (m, 2H), 7.56 (m, 3H), 7.31-7.39 (m, 4H), 2.73 (s, 3H). [Synthesis Example 7] Synthesis of Compound (MI-2) &lt;3_Mercapto- 4·(Synthesis of 6-(10-phenylfluoren-9-yl)naphthalene-2-yl)pyridine&gt; 4,5,5-tetradecyl-2-(6-(10-phenylfluoren-9-yl)naphthalene-2·yl-oxazepene (2.0 g), 4-> odor-3 - thiol ratio.

S 98 201226394 (1.0 g ), Pd(PPh3)4 (0.3 g), potassium citrate (1 7 g), 1,2,4-trimium (20 ml), second butanol (5 mi) Water (丨^1) was added to the flask, and the mixture was stirred at reflux temperature for 24.5 hours under a nitrogen atmosphere. After the completion of the heating, the reaction solution was cooled to room temperature, and water and toluene were added for liquid separation. The solvent was removed by evaporation under reduced pressure, and the obtained solid was purified by methylene chloride column chromatography (yield: benzene/ethyl acetate = 95/5). Next, the obtained eluate was passed through a short activated carbon tube column to remove the coloring component. The crystals precipitated during the distillation of the obtained mash were distilled under reduced pressure, and further recrystallized in toluene to obtain the compound represented by (1-11-2), 3-methyl-4-(6-(10-). Phenylfluoren-9-yl)naphthalen-2-yl)pyridine (〇.5 g). The structure of the compound was confirmed by NMR measurement. ^-NMRCCDCla): 6=8.62 (s,lH) , 8.58 ( d,lH) , 8.13 (d,lH) , 8.06 (s51H) , 8.02 (d,lH) , 7.99 (s,lH) , 7.75 (d , 4H), 7.70 (dd, lH), 7.65 (t, 2H), 7.59 (t, 2H), 7.53 (m, 2H), 7.33-7.39 (m, 5H), 2.44 (s, 3H) ° [Synthesis Example 8] Synthesis of Compound (mi-3) &lt;Synthesis of 2-Methyl-5-(6-(10-phenylfluoren-9-yl)naphthalen-2-yl)pyridine&gt; 4, 4, 5,5-tetramethyl-2·(6-(1〇-phenylindole-9-yl)naphthalen-2-yl)-1,3,2-oxaborolan (2.0 g), 5 -Bromo-2-indenyl. Bipyridine (〇.8 g), Pd(PPh3)4 (0.15 g), potassium citrate (1.7 g), 1,2,4-trimethylbenzene (20 ml), second butanol (5 ml) Water (1 ml) was added to the flask, and the mixture was stirred at reflux temperature for 5 hours under a nitrogen atmosphere. After the heating was completed, the reaction solution was cooled to room temperature, and water and toluene were added for liquid separation. The solvent was distilled off under reduced pressure, and the obtained solid was purified by silica gel column chromatography (eluent: benzene/ethyl acetate 99 201226394. TV J J v^if = 95/5). The solid obtained by distilling off the solvent under reduced pressure was recrystallized from toluene to obtain the compound 2-mercapto-5-(6-(10-phenylg-9-yl)naphthalene_2_ represented by (M1_3). Base) pyridine (] 2 g). The structure of the compound was confirmed by NMR measurement. H-NMR (CDC13): 5 = 8.95 (m, lH), 8.20 (s, lH), 8.14 (d, lH), 8.01 (m, 2H), 7.96 ( dd, lH), 7.81 ( dd, lH) , 7.74 (m,4H) , 7.67 (dd,lH) , 7.63 (t,2H) , 7.57 (t,lH) , 7.52 (m,2H),7.30-7.37 (m,5H),2.67 (S,3H ). [Synthesis Example 9] Synthesis of Compound (MI-4) &lt;Synthesis of 3-mercapto-5-(6-(10-phenylfluoren-9-yl)naphthalen-2-yl)n Ratio η Setting&gt; 4,4,5,5-tetradecyl-2-(6-(10-phenylfluorenyl)naphthalen-2-yl)-1,3,2-dioxaborolan (2.0 g), 3-bromo-5-mercaptoacridine (〇.8g), Pd(PPh3)4 (0.3 g), potassium acetate (1.7 g), 1,2,4-trimethylbenzene (20 ml), Dibutanol (5 ml) and water (1 ml) were added to the flask, and the mixture was stirred at reflux temperature for 7.5 hours under a nitrogen atmosphere. After the completion of the heating, the reaction solution was cooled to room temperature, and water and toluene were added to carry out liquid separation. The solvent was distilled off under reduced pressure. The obtained solid was purified by chromatography on silica gel column chromatography (eluent: benzene/ethyl acetate). Next, the obtained eluate was passed through a short activated carbon tube column to remove the coloring component. The solvent was distilled off under reduced pressure, and heptane was added for reprecipitation to obtain a compound represented by (1-11-4): 3-methyl-5-(6-(10-phenylindolinyl)naphthalen-2-yl) Acridine (1.3 g). The structure of the compound was confirmed by NMR measurement. 'H-NMR (CDC13): 6=8.87 (m,lH), 8.51 (m,lH), 8.22 (S,1H), 8.15 (d,lH), 8.03 (m,2H), 7.89 (m,lH) )

100 201226394 4U55Upif 7.83 (dd,lH), 7.73 (m,4H), 7.67 (dd,lH), 7.63 (m,2H), 7.57( t,lH) , 7.52(m,2H) , 7.30-7.37 (m , 4H), 2.49 (s, 3H) ° [Synthesis Example 10] Synthesis of Compound (1-11-5) &lt;4·methyl-3-(6-(10-phenylfluoren-9-yl)naphthalene · Synthesis of 2_基定> 4,4,5,5-tetramethyl-2-(6-(10-phenylfluoren-9-yl)naphthalene-2-yl)-1,3,2- Oxygen sulphate glutamine (2.0 g), 3-wet-4 曱 n n Ί 盐 盐 盐 (1.0 g), Pd (PPh3) 4 (0.3 g), potassium phosphate (1.7 g), 1, 2,4·trimethylbenzene (20 ml), third butanol (5 ml) and water (1 ml) were added to the flask, and stirred under reflux for 7 hours under a nitrogen atmosphere. The mixture was cooled to room temperature, and water and toluene were added for liquid separation. The solvent was distilled off under reduced pressure. The obtained solid was purified by silica gel column chromatography (developing solvent: toluene / ethyl acetate = 95/5). The obtained eluate is passed through a short activated carbon tube column to remove the coloring component. The solvent is distilled off under reduced pressure. The obtained solid is recrystallized from toluene to obtain a compound represented by (M1_5) 4-mercapto- 3-(6-( 10-Phenylfluoren-9-yl)naphthalen-2-yl)pyridine (0.6 g). The structure of the compound was confirmed by NMR measurement. ^-NMR (CDC13) · 6 = 8.64 (s ,lH) , 8.55 (d,lH) , 8.14 (d,lH) , 8.06 (s,lH) , 8.02 (d,lH) , 7.99 (s,lH) , 7.76 (m,4H) ,7.70( dd, lH) , 7.63 (m, 2H) , 7.59 ( t, 2H) , 7.53 (m, 2H) , 7.32 - 7.39 (m, 4H) , 7.30 (d, lH) , 2.45 (s, 3H) 〇 [Synthesis Example 11] Synthesis of compound (1-11-6) &lt;2-mercapto-3-(6-(10-phenylfluoren-9-yl)naphthalen-2-yl ratio. Synthesis] 4, 4 ,5,5-tetradecyl-2-(6-(10-phenylfluoren-9-yl)naphthalene-2-101 201226394 base)-l,3,2-dioxaborolane (2.0 g) , 3-bromo-2-methylpyridine (0.8 g), Pd(PPh3)4 (0.15 g), potassium phosphate (1.7 g), 1,2,4-trimethylbenzene (20 ml), third Alcohol (5 ml) and water (1 ml) were added to the flask, and stirred at reflux temperature for 4 hours under a nitrogen atmosphere. After the heating is completed, the reaction solution is cooled to room temperature, and water and benzene are added for liquid separation. "Removing the solvent under reduced pressure" is carried out by a ruthenium column chromatography (developing solution: stupid / ethyl acetate = 95/5 The solid obtained was purified. Next, the obtained eluate was passed through a short activated carbon tube column to remove the coloring component. The solvent was distilled off under reduced pressure, and the compound represented by (1-11-6) was obtained by adding heptane to obtain the compound 2-methyl-3-(6-(10-phenylg-9-yl)naphthalene-2-yl group represented by (1-11-6). ) "Bitidine (U g). The structure of the compound was confirmed by NMR measurement. ^-NMRCCDCls): 6=8.60 (m, lH), 8.11 (d, lH), 8.05 (s, lH), 8.00 (d, lH), 7.96 (s, lH), 7·74 (m, 4H) , 7.69 (m, 2H), 7.63 ( m, 2H), 7.57 ( m, 2H), 7.52 ( m, 2H), 7.30-7.37 (m, 4H), 7_28 (m, lH), 2.66 (s, 3H) ). [Synthesis Example 12] Synthesis of Compound (1-11-8) &lt;Synthesis of 5-methyl-2-(6-(10-phenyl-9-yl)naphthalen-2-yl)n Ratio α ; 4,4,5,5-tetradecyl-2-(6-(10-phenylidene)-naphthalene-2-yl)-1,3,2-dioxaborolane (2.5 g ), 3#-2-mercaptopyridine (10g), Pd(PPh3)4 (0.15 g), potassium phosphate (2.1 g), 1,2,4-trimethylbenzene (2〇ml), second Alcohol ($ mi) and water (1 mi) were added to the flask and stirred at reflux temperature for 18 hours under nitrogen. After the completion of the heating, the reaction solution was cooled to room temperature, and the precipitated solid was collected by suction filtration. The obtained solid was purified by ruthenium column chromatography (developing solution: benzene). Next, will

102 201226394 40550pif The obtained eluate is passed into a short activated carbon tube to remove the coloring component. The solvent was distilled off under reduced pressure, and ethyl acetate was added for reprecipitation to obtain the compound 5-(indolyl-2-(6-phenyl)-9-yl)naphthalene-2 represented by (1-11-8). -yl)pyridine (1.5 g). The structure of the compound was confirmed by NMR measurement. ^-NMR (CDC13): 5 = 8.63 (m, 2H), 8.23 (dd, lH), 8.16 (d, lH), 8.00 (m, 2H), 7.86 (d, lH), 7.73 (m, 4H) , 7.60-7.67 (m, 4H), 7.56 (t, lH), 7.51 (m, 2H), 7.30-7.36 (m, 4H), 2.44 (s, 3H). [Synthesis Example 13] Synthesis of Compound (M1-39) &lt;5-Methyl-methyl-3,4'-linked ratio synthesis> 4-bromo-2-mercaptopyridine (13.8 g) was added The flask with toluene (i5 〇 ml) was cooled in an acetone/dry ice bath. To the solution was added dropwise a 1.6 Torr solution of n-butyl hexane (55 ml). After completion of the dropwise addition, the mixture was stirred for 1 hour while cooling in a propylene/dry ice bath, and zinc hydride tetradecylethylenediamine (29.3 g) and THF (45 ml) were added thereto, and the acetone/dry ice bath was removed and the temperature was raised. After warming to room temperature, toluene (20 ml), 3,5-dibromo-n-batch (no g) and Pd(PPh3) 4 (2.8 g) were added, and the mixture was stirred at reflux temperature for 2 hours. After cooling the reaction liquid to room temperature, in order to remove the metal ions of the catalyst, ethylenediaminetetraacetic acid tetrasodium salt monohydrate which is equivalent to about 3 times the molar amount of the target compound is added and dissolved in an appropriate amount of water. The resulting solution (hereinafter, abbreviated as EDTA·4Na aqueous solution) and benzene were separated by liquid. After removing the solvent under reduced pressure, the obtained solid was purified by silica gel column chromatography (eluent: toluene / ethyl acetate). At this time, refer to "Introduction to Organic Chemistry Experiment (1) 103 201226394 - Substance Treatment Method and Public Charm ^ , ,..

Synthesis&gt; 4,4,5,5·tetradecyl_2_(6_(1〇_phenylindolinyl)naphthalene_2_土)-1,3,2-dioxolane (2) 5 g), 5 养 2, _methyl _3, 4, _ 吼 匕 (匕 1 g), Pd (PPh3) 4 (〇.i5g), potassium hydride u 7g), 124_ tridecyl benzene ( 20 =, tert-butanol (5ml) and water (i mi) were added to the flask 'under nitrogen atmosphere' for 3 hours at reflux temperature. After heating, the reaction solution was cooled to room temperature, water and toluene were added. The liquid was separated. The solvent was evaporated under reduced pressure, and the obtained solid was purified by silica gel column chromatography (eluent: benzene/ethyl acetate = 1/1). Recrystallization from benzene to obtain the compound 2 represented by (M1_39), -mercapto-5-(6-(10-phenylfluoren-9-yl)naphthalen-2-yl)-3,4,- The structure of the compound was confirmed by NMR measurement. 1H-NMR (CDC13): δ = 9.11 (ιη, 1 Η), 8.92 (m, lH), 8.65 (d, lH), 8.28 (m,2H),8·17 (d,lH),8·05 (m,2H),7.87 (d,lH),.7.68-7.75 (m,5H),7.61 (m,2H),7.56 ( t,lH), 7.51(m,3H), 7.45(m,lH), 7.30-7.37 (m, 4H), 2.70 (s, 3H) [Synthesis Example 14] Synthesis of compound (1-14-2) s 104 201226394 40550pif &lt; 3_mercapto-4_(3-(10_(naphthalene) Synthesis of _2·yl) -9-yl)phenyl) occlusion&gt; Addition of 4,4,5,5-tetramethyl-2-(3-(10-(naphthalen-2-yl)indole- 9-yl)phenyl)-1,3,2-dioxapentanyl (2.5 g), 4-oxa-3-mercaptopurine hydrochloride (1.3 g), Pd(PPh3)4 (0.35 g), potassium acetate (3.2 g), 20 ml of 1,2,4-tridecylbenzene, 5 ml of third butanol, and 1 ml of water, and stirred at reflux temperature for 11.5 hours. The reaction solution was cooled to After the room temperature, the benzene and water were added for liquid separation, and the solvent was evaporated under reduced pressure, and the obtained solid was purified by silica gel column chromatography (eluent: benzene/ethyl acetate = 95/5). The obtained eluate was passed through a short activated carbon tube column to remove the coloring component. The solvent was distilled off under reduced pressure, and heptane was added for reprecipitation to obtain a compound represented by (M4_2) 3-mercapto-4-(3-( 10-(Naphthalen-2-yl)fluoren-9-yl)phenyl)pyridine (1.4 g) The structure of the compound was confirmed by NMR measurement. ^-NMRCCDC^) : 5=8.53 (s,lH) , 8.50 (d,lH) , 8.08 (dd,lH), 8.02 (m,lH), 7.97 (d,lH), 7.92 (m,lH), 7.70-7.78 (m, 5H), 7.48-7.63 (m, 6H), 7.35-7.39 (m, 2H), 7.29-7.34 (m, 3H), 2.41 (s, 3H). [Synthesis Example 15] Synthesis of Compound (1-14-3) &lt;Synthesis of 2-indolyl-5-(3_(10-(naphthalene-2-yl)indole-9(yl)phenyl)) Add 4,4,5,5-tetradecyl_2_(3-(1〇-(naphthalen-2-yl)indoleyl)phenyl)-1,3,2·dioxaborolan ( 2.5 g), 5-bromo-2-indenyl. Bipyridine (1.〇g), Pd(PPh3)4 (0.35 g), potassium acidate (3.2 g), 1,2,4-trimethylbenzene 20 m Bu 105 201226394 40550pif second butanol 5 m 1 ml of water was stirred at reflux temperature for 8 5 hours. After the reaction solution was cooled to room temperature, the precipitated solid was collected by suction filtration. The obtained solid was purified by Shih Hose column chromatography (eluent: toluene / ethyl acetate = 95/5). Next, the obtained eluate was passed through a short activated carbon tube column to remove the coloring component. The solvent was distilled off under reduced pressure, and the obtained ethyl acetate was washed to obtain the compound 2 represented by (1-14_3) = -5-(3-(10-(naphthalen-2-yl)fluoren-9-yl) Phenyl) π is pyridine (丨 5 g). The structure of the compound was confirmed by NMR measurement. ^-NMRCCDC^): 6=8.45(m,lH), 8.08(d,lH)5 8.03 (m,lH), 7.99 (S,1H), 7.93 (m,lH), 7.87 (dd,lH), 7.70-7.81 (m,7H), 7.57-7.63 (m,3H), 7.54 (m,lH), 7.30-7.40 ( m4H) 7.23 (d,lH), 2.61 (S,3H). 'Synthesis of compound [Synthesis Example 16] Compound (i-14-u) &lt; Synthesis of 5-act-6-methyl-2,2'-bipyridyl> = 2|6·methyl(tetra) ( 5.2g) and cyclopentylmethyl scale (9) methanol / dry ice cooling. To the solution was added dropwise a hexane solution of butyl ketone (22 ml). After the completion of the dropwise addition, the mixture was stirred for 2 hours while being cooled in a dry ice, and zinc hydride was added to the aluminum/blue dry bath and the temperature was raised. In the room temperature > U added 2,5-monobromopyridinium g) and pd (pp at the temperature of 1 S丨irt do not g)

• When 4N H. After cooling the reaction solution to room temperature, EDTA was added and the benzene was reduced to carry out liquid separation. After the removal of the solvent, the residue was removed by a gel column chromatography (expansion liquid: a solid obtained by a solution. At this time, the rate of ethyl acetonitrile in the developing solution was slowly increased to dissolve the target. Then, the solvent was distilled off under reduced pressure, and the obtained solid was recrystallized from heptane to obtain 5-bromo-6,-mercapto-22, pyridine (1.4 g). ' &lt; 61-methyl· Synthesis of 5-(3_(10_(naphthalene-2-yl)indolinyl)phenyl from 2,,indenidine&gt; Addition of 4,4,5,5-tetradecyl_2_(3_(10_(naphthalene) _2·yl)蒽_9_yl)phenyl)-1,3,2-dioxaborolan (2 〇g), 5_ desert_6,_mercapto-2,2,_bipyridine (1·0 g), Pd(pph3)4 (0.15 g), squaring clock (1.7 g), ι, 2,4-trimethyl stupid 20 ml, third butanol 5 m b, and water 1 m The mixture was stirred at reflux temperature for 7.5 hours. After the reaction mixture was cooled to room temperature, the precipitated solid was collected by suction filtration. Purified by column chromatography (eluent: toluene/ethyl acetate = 95/5) The obtained solid was directly suction-filtered using a Kiriyama funnel coated with activated carbon to remove the colored component. The solvent was removed, and ethyl acetate was added for reprecipitation to obtain a compound 6'-mercapto-5-(3-(10-(naphthalen-2-yl)fluoren-9-yl) represented by (1-14-11). Phenyl)-2,2'-bipyridyl (1. 2g). The structure of the compound was confirmed by NMR. ^-NMR (CDC13): 5 = 9.03 (m,lH), 8.49 (dd,lH), 8.22 (d,lH) , 8.09 (m,2H) , 8.03 (m,lH) , 8.00 (s,lH), 7.93 (ιη,ΙΗ) , 7.87 (d,lH) , 7.68-7.83 (m,7H) , 7.55-7.64 (m, 4H), 7.30-7.40 (m, 4H), 7.17 (d, 1H), 2.65 (s, 3H). [Synthesis Example 17] Synthesis of Compound (1-14-12) &lt; Synthesis of 5-bromo-5'-fluorenyl-2,2'-bipyridine > THFfr ' of 107 201226394 40550pif added with 2-bromo-5-mercaptopyridine (1.7 g) and THF (5 ml) To the solution, 2 parts of isopropyl chloride was added dropwise for 3 5 hours of hydrazine &lt; 5ϊη1). After the addition was completed, the ice bath was removed and stirred at room temperature, and cooled again in an ice bath to add chlorine. Derivatives of tetramethyl bethane (2d f after removing the ice bath and warming to room temperature, add 2,5-dibromopyridinium. Add ~(G.35 g)' to mix U and toluene at reflux temperature Add EDTA · 4Na aqueous column after cold to room temperature Chromatography. After distilling off the solvent under reduced pressure, it was purified by purifying the η solution of phthalocyanine: benzene/ethyl acetate = 9/m. 5. The solvent was removed by pressing ==, and the money was added to re-deep the temple to obtain 5_&gt; 5-methyl-2, 2.♦ ratio (15g). Combination of I: methyl _5L (M1G•(naphthalene·2·fine) phenyl)·2,2,♦ than bite ^ ^, 5'5, methyl o (10) · (naphthalene-2-yl)蒽_9 base) benzene ^, oxalate pentane (2 〇 g), 5 _ .5, _ methyl 2, 2, _. It is better than the mouth to determine the best policy i, Γ (ρρί3) 4 (3) · 15 g), potassium phosphate (1.7 g), like - trimethyl I Γ, third butanol 5 m and water 1 m b at the reflux temperature to cool the liquid to the chamber After warming, add toluene and water to remove the solvent, and purify the obtained solid by ruthenium column chromatography (expanded ^1=/^ vinegar = 95/5) to obtain the brittle carbon tube. Column to remove the coloring component. Lai steam de-cooling agent 'addition of acetic acid, the purpose of re-sinking, the obtained solids into - ^ = recrystallization in the present 'obtained (M4_12) represented by the compound 5 · mercapto-5 ·- (3. (naphthalene·2_base) onion) phenyl) 2,2, lead bite (丄2

Ο J

S 108 201226394 The structure of the compound was confirmed by NMR measurement. ^-NMRCCDC^): 5 = 9.03(m,lH), 8.52(s,lH), 8.44 (dd,lH) , 8.33 (d,lH) , 8.09 (m,lH) , 8.03 (m,lH) , 8.00 (s,2H) , 7.93 (m,lH) , 7.87 (m,lH) , 7.73 - 7.83 (m,6H), 7.56-7.66 (m,5H) ,7.31-7.39 (m,4H) ,2.41 ( s, 3H). [Synthesis Example 18] Synthesis of Compound (1-14-13) &lt; Synthesis of 5'-Bromo-4-methyl-2,2'-bipyridine> 2-Bromo-4-indolylpyridinium added A flask of 6.9 g and THF (20 ml) was cooled in an ice bath, and a solution of 2% isopropylmagnesium hydride in THF (24 ml) was added dropwise. After the completion of the dropwise addition, the ice bath was removed and the mixture was stirred at room temperature for 1 hour, and then cooled again in an ice bath to add zinc trimethylethylenediamine (12.1 g). After removing the ice bath and warming to room temperature, 2,5-dibromo 0 was added (9.5 g) and Pd(PPh3) 4 (1.4 g) was stirred at reflux temperature for 25 hours. After the reaction solution was cooled to room temperature, an aqueous solution of EDTA·4Na and toluene were added to carry out liquid separation. After distilling off the solvent under reduced pressure, the obtained solid was purified by silica gel column chromatography (eluent: toluene/ethyl acetate = 9/1). The solvent was distilled off under reduced pressure, and the obtained solid was recrystallized from heptane to give 5,················ &lt;4_曱基_5'-〇(1〇·(Naphthalene_2_yl)蒽_9_yl)phenyl)_2,2,·bipyridine Synthesis&gt; Add 4,4,5,5 -tetradecyl_2_(3_(10_(naphthalen-2-yl)indole-9)yl)-1,3,2-dioxapentane (2.〇g), bromine_4· Methylation d ratio bite (1.2 g), Pd (PPh3) 4 (0.15 g), squaric acid clock (1 7 g), 丄 斗 · · trimethyl stupid 20 m dibutanol 5 m b and water 1 ^ Bu stirred at reflux temperature 109 201226394 40550pif mixed for 16 hours. After the reaction solution was cooled to room temperature, toluene and water were added to carry out liquid separation. The solvent was removed by vacuum distillation, and the obtained solid was purified by a silica gel column chromatography (eluent: benzene/ethyl acetate = 95/5), and the obtained solvent was passed through a short activated carbon column. Remove the coloring ingredients. The solvent was distilled off under reduced pressure, and washed with heptane to obtain the compound 4-methyl-5'-(3-(10-(naphthyl)anthracene)benzene represented by (1-14-13). Base)_2,2,_bipyridinium (1.4 g) The structure of the compound was confirmed by NMR measurement. b-NlVtRXCDCls): δ = 9·04 (πι, 1Η), 8.55 (d, lH), 8.47 (dd, lH), 8.28 (S, 1H), 8.11 (dd, lH), 8.09 (d, lH) , 8.03 (m, lH), 8.00 (s, lH), 7.93 (m, lH), 7.88 (d, lH), 7.73.7 83 (m, 6H), 7.57_7.63 (m, 4H), 7.30 -7.40 (m, 4H), 7_14 (d ih) 2.45 (s, 3H). [ 'Synthesis Example 19] Synthesis of Compound (1-14-15) &lt;Synthesis of 5-Bromo-6'-fluorenyl-2,3'-bipyridine]&gt; 5-Bromo-2- A flask of hydrazinium (3.4 g) and THF (1 〇mi was cooled in an ice bath, and 2 M of isopropylmagnesium THF solution (ll ml) was added dropwise to the solution. After the addition was completed, the ice was removed. After warming for 3 hours, it was cooled again in an ice bath, and zinc hydride tetramethylamine (5.5 g) was added. After removing the ice bath and warming to room temperature, add 2 5 _ 2 $ bite (4.7 g) and Pd(PPh3)4 (0·7 g), 5 hours at the reflux temperature. After cooling the reaction solution to room temperature, EDTA · 4Na water was added to δ.) and benzene was used for liquid separation. The solid obtained in the decompression of the steamed crane by the Shixi rubber column chromatography (Exhibition: A stupid / acetic acid ethyl acetate = 7 / 3) pure 110 201226394 40550pif 'obtained 5 · bromo-6,-mercapto-2 , 3'-bipyridyl (1.5 g). &lt;6'-Mercapto-5-(3·(10·(naphthalene-2-yl)fluorene-9-yl)phenyl)_2,3,-bipyridine Synthesis&gt; Add 4,4,5, 5-tetramethyl-2-(3-(10-(naphthalen-2-yl)fluoren-9-yl)phenyl)-1,3,2-oxaoxalan (2 〇g), 5 -Mix-6'-mercapto-2,3'-linked η 〇 〇 (1.2 g), Pd (PPh3) 4 (0.15 g), potassium phosphate (1.7 g), 1,2,4-trimethyl Stupid 25 m of third butanol 5 ml, and 1 m of water were mixed for 5 hours at reflux temperature. After cooling the reaction mixture to room temperature, the precipitated solid was collected by suction filtration, washed with decyl alcohol, and washed with ethyl acetate. Subsequently, purification was carried out by a silica gel column chromatography (developing solution: hydrazine/ethyl acetate = 4/1). The obtained eluate was passed through a short activated carbon tube column to remove the coloring component. The solvent was distilled off under reduced pressure, and the obtained solid was further recrystallized from gas benzene to obtain the compound 6 represented by (M4-15), -mercapto-5-(3-(10-(naphthalen-2-yl)蒽-9-yl)phenyl)-2,3'-linked. Bisidine (1.3 g). The structure of the compound was confirmed by NMR measurement. ^-NMR (CDC13) * 5 = 9.13 (m, lH), 9.07 (m, lH), 8.28 (dd, lH), 8.01-8.ll (m33H), 8.00 (s, lH), 7.93 (m, lH), 7.86 (m, lH), 7.73-7.83 (m, 7H), 7.57-7.64 (m, 4H), 7.31-7.39 (m, 4H), 7.28 (d, lH), 2.63 (s, 3H) [Synthesis Example 20] Synthesis of Compound (1-14-16) &lt;Synthesis of 5-bromoindolyl-2,3r-bipyridyl> 3·Bromo-5-mercaptopyridine (3.4 g) and A flask of THF (10 ml) was cooled in an ice bath, and a solution of 2% isopropylmagnesium chloride in THF (11 ml) was added dropwise. After the completion of the dropwise addition, the ice bath was removed and stirred at room temperature for 111 hours at room temperature for 111 hours. Then, it was cooled again in an ice bath, and zinc tetramethylethylenediamine (5.5 g) was added. After removing the ice bath and warming to room temperature, 2,5-dibromo-bite (4.7 g) and Pd(PPh3)4 (0.7 g) were added and stirred at reflux temperature for 5 hours. After the reaction solution was cooled to room temperature, an aqueous solution of EDTA·4Na and toluene were added to carry out liquid separation. After distilling off the solvent under reduced pressure, the obtained solid was purified by silica gel column chromatography (eluent: toluene/ethyl acetate = 7/3) to give 5---5--methyl-2,3 '-Bipyridine (1.4 g). &lt;5'-Methyl_5_(3-(1〇-(naphthalene-2-yl)indole-9-yl)phenyl)_2,3'-bipyridine Synthesis&gt; Add 4, 4, 5, 5-Tetramethyl-2-(3_(10-(naphthalene-2-yl)indoleyl)phenyl)-1,3,2-dioxaborolan (2.〇g), 5-__6 , _methyl_2,3,· 吡 咬 (l_2g), Pd(PPh3)4 (〇.i5g), potassium phosphate (i.7g), 1&gt; 2,4_trimethyl 25ml, second 5 ml of alcohol and 1 ml of water were mixed for 5 hours at reflux temperature. After the reaction solution was cooled to room temperature, the precipitated solid was collected by suction filtration, washed with methanol, and washed with ethyl acetate. Subsequently, it was purified by ruthenium column chromatography (developing solution: benzene/ethyl acetate = 4/1), and the obtained eluate was passed through a short activated carbon tube column to remove the colored component. The solvent was distilled off under reduced pressure, and the obtained solid was further recrystallized from gas benzene to obtain the compound 5'-mercapto-5-(3·(1〇-(naphthyl)) represented by (1-14-16). Onion _9·yl)phenyl)-2,3,-bipyridine (1.3 g). The structure of the compound was confirmed by NMR measurement. 'H-NMRC CDC13) : 6 = 9.08 ( m,lH) , 9.04 ( s,lH) , 8.50

UlH), 8.21 (s, ih), 8.09 (m, 2H), 8.04 (m, lH), 8.00 (s, lH), 7.93 (m, lH), 7.73-7.88 (m, 8H), 7.62 (m , 4H),

S 112 201226394 40550pif 7.31-7.40 (m, 4H), 2.45 (s, 3H). [Synthesis Example 21] Synthesis of a compound &lt;5_漠_4'-mercapto-2,3'_吼吼σ定的奋成&gt; 3-Dimethyl-4-methylindole spray (5 2g) The flask was cooled in an ice bath, and a solution of 2 mg of THF was added dropwise to the solution, 7 m). After the dropwise addition was completed, the dipropyl oxime was stirred for 9 hours, and then again cooled in an ice bath. 1 at room temperature. Next, add zinc telluride, and then remove the ice bath and warm to room temperature (7) g). Pd- 】37 (British Johnson letter Wanfeng Gongguang - shoulder ratio

(25 ml), spoiled for 6 hours at reflux temperature. The reaction and the employment of P: steaming: = wide aqueous solution "benzene": diphenyl / acetic acid S; / purified by Jingzhu chromatography (expansion liquid · · · · · · · · · , the obtained solid _ gen is washed and washed to obtain 5^:4=C; r lianqi (2.4 g). ^^T^-2,3-methyl 5-(3-(10-(奈_ 2-based) fluoren-9-yl)phenyl)_2,3'-linked alpha ratio. Synthesis of synthesis &gt; = addition of a 4,4 5,5-tetramethyl-neo(naphthalene-2-yl) anthracene Base) benzene storm -, dioxin pentoxide ring (2 〇 g), 5 _ desert _6, _ methyl 2, 3 | _ „ „ 咬 咬 ^ ^, Pd (PPh3) 4 (0.15g) Potassium acid (1.7g), 1,2,4-trisole 25mi, flute-^ fell 5 spear dibutanol 5 ml, and water 1 ml, stir the gossip at reflux temperature. After the reaction solution was cooled to room temperature, 'toluene and water were added to carry out liquid-liquid knife decompression*, and the solvent was removed by steaming, and the solvent was purified by silica gel column chromatography (extraction/acetic acid ethyl acetate = 7/3). The solid obtained was passed through a short activated carbon tube column of the obtained 113 201226394 40550 pif to remove the coloring component. The solvent was removed by distillation under reduced pressure, and the obtained solid was further recrystallized from toluene to obtain the compound 4'-mercapto-5-(3-(10-(naphthalene)- represented by (1-14-17). 2-based) 蒽-9-yl)phenyl)-2,3'-linked ratio (0.7 g). The structure of the compound was confirmed by NMR measurement. ^-NMR (CDC13): 6 = 9.09 (s,lH) , 8.67 (s,lH) , 8.51 (d,lH) , 8.09 (m,2H) , 8.03 (m,lH) , 8.00 (m,lH) , 7.93 (m,lH) , 7.88 (d,lH), 7.73-7.84 (m,6H), 7.61 (m,4H), 7.52 ( d, 1H) , 7.31-7.40 ( m,4H) , 7.23 ( d ,1H), 2.46 ( s,3H) 〇 [Synthesis Example 22] Synthesis of Compound (1-14-18) &lt;Synthesis of 5-N--2'-Mercapto-2,3'-bipyridyl&gt; A flask to which 3-bromo-2-methylpyridine (5.2 g) and THF (10 ml) were added was cooled in an ice bath, and 2 μ of a solution of isopropylmagnesium chloride in THF (π ml) was added dropwise. After completion of the dropwise addition, the ice bath was removed and stirred at room temperature for 2 hours, and then cooled again in an ice bath, and gasified tetradecylethylenediamine (8.3 g) was added. After removing the ice bath and warming to room temperature, 2,5-dibromopyridyl = (7.1 g), Pd(PPh3)4 (l.〇g) and xylene (1 〇ml) were added at reflux.

Stir at temperature for 7 hours. After the reaction solution was cooled to room temperature, EDTA 4Na water was added; the solution and the benzene were separated by liquid. After removing the solvent under reduced pressure, the obtained solid was purified by silica gel column chromatography (eluent: toluene/ethyl acetate = 4/1) to afford 5-bromo-2,-indole-2. 3,-bipyridine (1.3 g). &lt;2'·Mercapto-HHIO-(naphthyl)fluoren-9-yl)phenyl)_2,3,_0-pyridine synthesis&gt; Add M,5,5·tetramethyl_2_(3_ (10(naphthalene-2-yl)anthracene)benzene 114 201226394 40550pif base)_1,3,2-oxaxahedral oxime 2 〇ς& phenyl benzene 25 m butylbutanol 5%, (Ug) 1, 2, 4 · 2 surnames 19 glare. Knee G _ V, and water lm are agitated at reflux temperature, and then added toluene and water to remove the liquid. Secret _ remove agent, the obtained solid was purified by the hose column continuation method (expanded 乙乙广4/1), and the obtained 3 carbon tube column was removed to remove the coloring component. The solvent was removed by distillation under reduced pressure, and the compound 2'·methyl Zheng (Caixin thiol)-2,3'-bipyridine (0.8 g) which was precipitated by the absorption set was hunted. The structure of the compound was confirmed by NMR measurement. ^-NMR CCDCI3): 6 = 9.08 (m5lH), 8.57 (mlH) 7.99-8.10 (m,4H), 7.92 (m,lH), 7.88 (d,lH), 7.73-7.83 (m,7H), 7.61 (m, 4H), 7.51 (dd, lH), 7.30-7.40 (m 4H) 7.25 (m, lH), 2.66 (s, 3H). [Synthesis Example 23] Synthesis of Compound (1-14-20) &lt;Synthesis of 5-bromo-3'-fluorenyl-2,4'-bipyridine> 4-Bromo-3-methyl group was added ° ratio. A flask of fixed (5.0 g) and THF (30 ml) was cooled in a dry ice/methanol bath, and a 2M solution of isopropylmagnesium chloride in THF (16 ml) was added dropwise. After the completion of the dropwise addition, the cooling bath was removed and stirred at room temperature for 2.5 hours, and then cooled in an ice bath to add zinc trimethylethylenediamine (8.0 g). After removing the ice bath and warming to room temperature, 2,5-dibromo-n-bit (7.6 g) and Pd(PPh3)4 (1.0 g) were added, and the mixture was refluxed for 2 hours. After the reaction solution was cooled to room temperature, a liquid separation was carried out by aqueous solution of Taiga edta·115 201226394 4Na and ethyl acetate. After distilling off the solvent under reduced pressure, the obtained solid was purified by silica gel column chromatography (eluent: benzene/ethyl acetate = 5/1) to obtain 5-bromo-31-mercapto-2,4 , _bipyridine (5.6 g). &lt;3'-Methyl·5·(3-(1〇-(naphthalen-2-yl)indole-9-yl)phenyl)-2,4,·Synthesis of hydrazine bite&gt; Add 4,4 ,5,5·tetradecyl-2-(3-(10-(naphthalen-2-yl)fluoren-9-yl)phenyl)-1,3,2-dioxaborolan (2.〇 g), 5-bromo-3'-methyl-2,4,-bipyridyl (1.2 g), Pd(PPh3)4 (0.15 g), potassium phosphate (1.7 g), 1,2,4-trimethyl 1 ml, 1 ml of third butanol, and 1 ml of water were stirred at reflux temperature for 4 hours. After the reaction solution was cooled to room temperature, water was added, and the precipitate was collected by suction filtration. The obtained solid was washed with water and decyl alcohol, and then purified by an NH-based modified silicone (DM1020: manufactured by Fuji Chemical Co., Ltd.) column chromatography (developing solution: toluene) to obtain (1-14-20). The compound 3, methyl-5-(3-(10-(naphthalen-2-yl)fluoren-9-yl)phenyl)-2,4,-bipyridine (1.7 g). The structure of the compound was confirmed by NMR measurement. 1H-NMR (CDC13) · 5 = 9.09 (m, lH), 8.56 (s, lH), 8.55 (d, lH), 8.10 (m, 2H), 8.03 (m, lH), 8.00 (d, lH) , 7.93 (d, lH), 7.88 (d, lH), 7.73-7.83 (m, 6H), 7.61 (m, 4H), 7.53 (d, lH), 7.31-7.41 (m, 5H), 2.44 (s , 3H). [Synthesis Example 24] Synthesis of Compound (1-11-18) &lt; 2'-Mercapto-5-(6-(10-phenylfluoren-9-yl)naphthalen-2-yl) 2,3'· Union. Synthesis of specific bite &gt; 4,4,5,5-tetradecyl-2-(6-(10-phenylfluoren-9-yl)naphthalene-2-

S 116 201226394 40550pif base)-l,3,2-dioxaborolan (2〇g), 5|2 (W), ed.), ( ^ phenylbenzene (20ml), third butanol (5ml) And water ^ U, 4- dimethyl, under nitrogen atmosphere, at reflux temperature _8 = added to the flask 'after cooling the reaction solution to room temperature, by suction data collection: out = 曱 曱 S Washed and washed with ethyl acetate. — Column chromatography (developing solution: toluene / E-tank) The obtained eluate was passed into a short activated carbon tube::, =, and the solvent was removed by distillation. By sucking the picker color / knife. minus nn ^ &quot; straw and / / know the solids precipitated, get i 2:, I two compounds 2 '_ methyl _ 5 you (10) phenyl onion-9 -Base) Nai 2·yl) 2,3 - η than bite (1 1 g). } The structure of the complex was determined by NMR. 8 23(^1= (RCDCl3) : δ = 9·17 U,1H), 8.6G (_), 8.23^3,1H), 8.19 (m,2H), 8.06 (m,2H),7.87(dd5lH 7. 5( dd,lH), 7.73( m,4H), 7.69( dd?lH), 7.55-7.65( m^H)5 7.51 Cm,2H), 7.26-7.37 (m,5H),2.73 ( s3H) 〇, the simple biological compound can be synthesized by a compound which is suitable for changing the raw material, and by the method according to the above synthesis example. Hereinafter, in order to explain the present invention in detail, an example of an organic EL device using the present invention is disclosed, but the present invention is not limited to the above-described 0 production examples 1 to 4 and comparative examples! In the element of Comparative Example 2, the time (hour) at which the (IV) start voltage (7) and the brightness of 90% or more of the initial value were maintained in the strange current drive test were measured. Hereinafter, an example and a comparative example will be described in detail in 117 201226394. The material compositions of the respective layers of the produced Examples 1 to 4 and Comparative Examples 1 to 2 are shown in Table 1 below. Table 1

Hole injection layer hole transport layer light-emitting layer electron transport layer host dopant example 1 HI NPD AB 1-7-74 Example 2 HI NPD AB 1-7-26 Example 3 HI NPD AB 1-7-98 Example 4 HI NPD AB 1-7-96 Comparative Example 1 HI NPD ABC Comparative Example 2 HI NPD ABD In Table 1, "HI" is N4, N4'-diphenyl-N4, N4'-bis (9-phenyl-9H) -oxazol-3-yl)-[1,Γ-biphenyl]-4,4'-diamine 'NPD' is N4,N4'-di(naphthalen-1-yl)-N4,N4'- Phenyl-[Ι,Γ-biphenyl]-4,4'-diamine, compound (A) is 9-phenyl-10-(4-phenylnaphthalen-1-yl) oxime, compound (Β) is Ν5,Ν5,Ν9,Ν9-7,7-hexaphenyl-711-benzo[[;;] burial-5,9-diamine, compound (〇9,10-二([2,2'-linked Acridine]-5-yl)anthracene, compound (D) is 9,10-bis(tetradecyridin-3-yl)naphthalen-1-yl)anthracene. These compounds are formed in an electron transport layer and a cathode. The chemical structure of "Liq" used in the layer between them is revealed as follows.

118 201226394 40550pif

[Example 1] <Elements of the electron transport layer of (1·7·74) (IV)> The IT〇 of a film having a thickness of 丨(10) nm by sputtering was polished to 26 mm×28 mm×〇 at 150 nm. A 7-sided glass substrate (〇pt〇··i ΐΐ) is used as a transparent supporting substrate. The transparent support substrate is held by a substrate (manufactured by Showa Vacuum Co., Ltd.); key ΓΪΓ: steamed _ boat with HI, rafted with Hua plating added with Li, and steamed with compound (A) added舟 ^ 119 201226394 4 11 B (B) vapor deposition indium boat, addition of a molybdenum boat for compounding, molybdenum boat for vapor deposition with Liq, Su-4), vapor deposition with silver and vapor deposition Tungsten boat. The molybdenum boat with magnesium is added to the IT0 film of the transparent support substrate, and the pressure is reduced to 5xl〇·4 Pa according to the vacuum chamber. First, the following layers are twisted. The kiln layer for HI was added to the boat so that the film thickness was 4 〇 nm, and then vapor deposition was carried out by heating the surface of the NPD to form a hole transfer method. The retanning film thickness is 3 〇 nm. There are compounds (4) 岐 舟 与 私 私 私 私 私 ' ' ' 加热 加热 加热 加热 加热 加热 加热 ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' . To adjust the evaporation rate. The material was heated to have a 彳5:5 plating method. The plating layer was used to form a vapor deposition layer having a film thickness of 15 nm (_7: 74). The evaporation rate of each layer is 〇.〇1 nm/sec~==, and the formation of electrons is followed by 'heating the method of adding Liq to the steam. (10)nm/sec~G] position/sec _ ^ becomes 1 (10) The crucible boat was vapor-deposited in a manner of adding 100 to form a cathode. At this time, the J-thickness becomes 0.1 (10) / sec to _ speed, and the element becomes the element at the vapor chain speed. The cathode was formed in a manner of 0 nm/sec, and organic electroluminescence light was obtained by adding a DC core and applying a galvanic/silver electrode as a cathode to a blue luminescence having a wavelength of about 460 nm. In addition, it is difficult to obtain the current density of the initial luminance leak cd/m2.

S 120 201226394 40550pif Current drive test, the result of driving the test start voltage is 7.33 V, maintaining the initial value of 90 ° /. The brightness of (1800 cd/m2) or more is 45 hours. [Example 2] &lt;Component for using compound (1-7-26) for electron transport layer&gt; Except that compound (1-7-74) was replaced with compound (1-7-26), by way of example The method of 2 obtained an organic EL element. A constant current driving test was carried out by using an IT crucible electrode as an anode and a magnesium/silver electrode as a cathode to obtain a current density of an initial luminance of 2000 cd/m. The drive test start voltage was 6·36 V, and the brightness of the initial value of 9〇% or more was maintained at 151 hours. [Example 3] &lt;Component for using compound (1-7-98) for electron transport layer&gt; Except that compound (1-7-74) was replaced with compound (1-7-98), by way of example The method of 2 obtained an organic EL element. A constant current driving test was carried out by using a ruthenium electrode as an anode and a magnesium/silver electrode as a cathode to obtain a current density of an initial luminance of 2000 cd/m2. The drive test start voltage was 7.34 V, and the brightness of the initial value of 9〇% or more was maintained for 265 hours. [Example 4] &lt;Component for using compound (1-7-96) for electron transport layer&gt; Except that compound (1-7-74) was replaced with compound (^7-96), by way of example 2 The method of obtaining an organic EL element. Taking the IT 〇 electrode as the anode and the off/silver _ as the cathode, the strange current _ test was carried out, such as the initial brightness of 2000 cd/m2. Drive test 121 201226394 40550pif The test start voltage is 5.33 V. The time for maintaining the brightness of the initial value or more is 103 hours. [Comparative Example 1] An organic EL device was obtained by the method according to Example 1, except that the compound (H96) was replaced by the compound (C). The constant current driving test was carried out by using a ΙΤ0 electrode as an anode '2 with a magnesium/silver 1 pole as a cathode for obtaining an initial luminance of 2000 cdm and &quot;丨. As a result, the driving test was started at 5.G6 V, keeping the initial value. The above brightness time is 6 hours. [Comparative Example 2] An organic EL device was obtained by the method according to Example 1, except that the compound (1-7-96) was replaced by the compound (D). The ITQ electrode was used as the anode '2 with the town/silver electrode as the cathode' by the electro-mechanical test for obtaining the initial luminance of 2 cd/m2. As a result, the driving test start voltage was 5.05 V', and the time for maintaining the brightness of 9 ()% or more of the initial value was 10 hours. The above results are summarized in Table 2.

Table 2 Time (hours) at which the electron transport layer maintains the brightness above 90«^_ of the initial value. Starting voltage (V) Example 1 1-7-74 45 7.33 Example 2 1-7-26 151 6.36 Example 3 1-7- 98 265 7.34 Example 4 1-7-96 103 5.33 - ' 丨!· 5.06 Comparative Example 1 C Comparative Example 2 D 10 5.05 122 201226394 40550pif The components of Example 5 to Example 20 and Comparative Example 3 to Comparative Example 5 were prepared and measured separately. The drive start voltage (V) in the constant current drive test and the time (hour) at which the luminance of 90% or more of the initial value is maintained. Hereinafter, examples and comparative examples will be described in detail. The material constitution of each of the elements of Examples 5 to 20 and Comparative Examples 3 to 5 produced was shown in Table 3 below. table 3

Hole injection layer hole transport layer light-emitting layer electron transport layer host dopant example 5 HI HT EF 1-11-1 Example 6 HI HT EF 1-11-2 Example 7 HI HT EF 1-11-3 Example 8 HI HT EF 1-11-4 Example 9 HI HT EF 1-11-5 Example 10 HI HT EF 1-11-39 Example 11 HI HT EF 1-14-2 Example 12 HI HT EF 1-14-3 Example 13 HI HT EF 1-14-11 Example 14 HI HT EF 1-14-12 Example 15 HI HT EF 1-14-14 Example 16 HI HT EF 1-14-15 Example 17 HI HT EF 1-14-16 Example 1.8 HI HT EF 1-14-18 Example 19 HI HT EF 1-14-20 Example 20 HI HT EF 1-11-18 Comparative Example 3 HI HT EFG Comparative Example 4 HI HT EF Η Comparative Example 5 HI HT EFI In Table 3 , HT is Ν-([1,Γ-biphenyl]-4-yl)-9,9-diindenyl 123 201226394 _____^11 _N-(4_(9-phenyl-9H-carbazol-3-yl) Phenyl)-9H-S-2-amine, compound (E) is 9-(4-(naphthalen-1-yl)phenyl)_1〇_phenylindole, and compound (F) is 4,4'- ((7,7-diphenyl-7H-benzo[c]-5,9-diyl)bis((phenyl)amino))bisacetonitrile, compound (G) is 4,-(4_ (1〇-(naphthalene-2-yl)fluoren-9-yl)phenyl)-2,2,:6,,2,,-triplet ratio bite compound (H) 3-(6-(10-phenylfluoren-9-yl)naphthalen-2-yl) hydroxy-' compound (I) is 6-(4-(1〇-(naphthalenyl)anthraceyl)phenyl ) _2, 4, · 联 ° bite.

[Example 5]

S 124 201226394 4U55Upif <Components for Compounds for Electron Transport Layers> Glass substrates of 26 mm, mm x 〇.7 mm which were ground to 150 nm by a ruthenium made of a film having a thickness of 180 nm (〇pt (Stock) manufacturing) as a phase branch board. The slab of the slab of the slab of the steamed slab (7) The shovel, the 1st force, the addition of a compound key boat, and the addition of Liq's 'use: compound (1)1·1) are steamed with silver and steamed. One uses a molybdenum boat, adds a _ _ boat and adds an empty groove to form a layer. The way to be true: : Li Qiao: The boat for vapor deposition with HT: The heat is added as follows: The film thickness is 35nm, the inlet is 4 (7), the evaporation boat is used, (8) and the compound (F) are used for money (4) Yiguang layer. The plating rate of the compound is used. Secondly, the weight ratio of the steaming boat and the method of adding the compound (MM) to the steaming (4) into a thickness of 25 (10) is about 1:1. The second and the Llq degrees are 0.01 nrn / sec ~ i nm / sec. The vapor deposition rate of each layer is heated by adding a boat for vapor deposition of Llq, and the film thickness is 1 nm 125 201226394 40550 pif, and G.Gl nm/sec to ο" (10) is added, and the vaporization is performed by adding 迷. A, ,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, At this time: = the sub-ratio is 10:1 square f Μ magnesium and silver original 0.1 nm / sec ~ 1Gnm / y two speed ' at the steaming speed to become the component. The side of the spider is cut into a cathode, and the surface electric excitation light is obtained straight 4:::electric ί! is the anode, and the magnesium (10) is directly grasped the voltage, and the blue wavelength of about Wei nm is obtained by using the flow for obtaining the initial brightness 2__2. The density is controlled by a constant current drive test, and the result is that the start of the test is 4, and the brightness of the initial value of 9 G% (l_ed/m2) or more is maintained. [Example 6] ^ Element for the compound (1·11·2) for the f-transport layer> In addition to the compound (M1)), the organic EL device was obtained by the method according to Example 5 except that the compound (M1) was replaced with the compound (M12). . The ITO electrode was used as the anode '^/silver electrode as the riding pole, and the current-deficient (four) test was carried out by (4) obtaining the f-filament of the initial bright 诵 cd/m. The drive start voltage is 4.12 V, and the brightness between 9 ()% or more of the initial value is maintained for 85 hours. [Example 7] <Element for using the compound (1·11·3) for the electron transport layer> An organic method was obtained by the method according to Example 5 except that the compound (1-11-1) was replaced with the compound (1113). EL component. A constant current drive test was carried out using a ΙΤ0 electrode as an anode and a magnesium/silver electrode as a saccharide electrode by (4) obtaining a current density of an initial luminance of 126 201226394 40550 pif 2000 cd/m 2 . The driving test starting voltage was 3·78 V, and the time for maintaining the luminance of 9 〇% or more of the initial value was 97 hours. [Example 8] &lt;Component (^1-4) used for the electron transport layer element> An organic EL element was obtained by the method according to Example 5, except that the compound (Μ1·1) was replaced by the compound (1_H_4). A constant current driving test was carried out by using a ruthenium electrode as an anode and a magnesium/silver electrode as a cathode to obtain a current density of an initial luminance of 2000 cd/m2. The drive test start voltage was 3.95 V, and the brightness of the initial value of 9〇% or more was maintained for 83 hours. [Example 9] &lt;Component for using compound 0-11-5) for an electron transport layer&gt; An organic method was obtained by the method according to Example 5 except that the compound (iU1) was replaced with the compound (1-11-5). EL component. A constant current driving test was carried out by using an ITO electrode as an anode and a flag/silver electrode as a cathode to obtain a current intensity of an initial luminance of 2000 cd/m. The driving test start voltage was 3.88 V', and the time to maintain the brightness of 90% or more of the initial value was 93 hours. [Example 10] &lt;Component for using compound (1-11-39) for electron transport layer&gt; Organic EL was obtained by the method according to Example 5 except that the compound (Mi-ι) was changed to the compound (M1_39) element. The IT crucible electrode was used as the anode of the anode and the silver electrode was used as the riding pole, and the constant current driving test was carried out by obtaining the current density of the initial luminance of 127 201226394 40550 pif 2000 cd/m 2 . The drive test start voltage was 4.16 V, and the time above the initial value was 74 hours. [Example 11] &lt;Component for using compound (1-14_2) for electron transport layer&gt; In addition to the compound (1-1M) was changed to the compound (Bu 14-2), organic was obtained by the method according to Example 5. El component. A constant current driving test was carried out by using an ITO electrode as an anode and a magnesium/silver electrode as a cathode to obtain a current density of an initial luminance of 2000 cd/m2. The drive test start voltage was 3.61 V' while maintaining the brightness of 9 % or more of the initial value for 76 hours. [Example 12] &lt;Component for using compound (1-14-3) for electron transport layer&gt; An organic EL device was obtained by the method according to Example 5, except that the compound (Mlq) was replaced with the compound (M4_3). A constant current driving test was carried out by using an IT crucible electrode as an anode and a magnesium/silver electrode as a cathode to obtain a current density of an initial luminance of 2000 cd/m2. The drive test start voltage was 3.85 V, and the brightness between 9 G% or more of the initial value was maintained at 141 hours. [Example 13] <Element of Compound (V)) for Electron Transport Layer&gt; An organic EL element was obtained by the method according to Example 5 except that the compound (1-U_1) was replaced with the compound (M4-11). Taking the IT0 electrode as the anode '(10)/silver f pole as the cathode, by (iv) obtaining the initial brightness

128 201226394^ 2000 Constant current drive test was carried out with a current male of cd/m. The drive test start voltage was 4.16 V, and the brightness of the initial value of 9〇% or more was maintained for 162 hours. [Example H] &lt;Component for using compound (1-14-12) for electron transport layer> An organic EL device was obtained by the method according to Example 5 except that the compound (MM) was replaced with the compound (114-12). . A constant current driving test was carried out by using an IT crucible electrode as an anode and a magnesium/silver electrode as a cathode to obtain a current density of an initial luminance of 2000 cd/m2. The drive test start voltage was 3.87 V, and the brightness of the initial value of 9〇% or more was maintained for 75 hours. [Example 15] &lt;Component for using compound (1-14-14) for electron transport layer&gt; An organic EL device was obtained by the method according to Example 5, except that the compound (MM) was replaced with the compound (M4_14). The IT 〇 electrode was used as the anode '_/silver electrode as the cathode, and the constant current driving test was carried out by (4) obtaining a current density of an initial luminance of 2000 cd/m 2 . The driving test start voltage was 3·82 V ', and the time required to maintain the brightness of 9 ()% or more of the value was 227 hours. [Example 16] <Element of Compound (1-1M5) Electron Transport Layer> An organic anal element was obtained by the method according to Example 5 except that the compound (1-11-1) was changed to the compound (114·15). . Using a ruthenium electrode as the anode and a secret/(four) division as the cathode, the constant current drive test was carried out by the current density of 129 201226394 40550pif 2000 cd/m2. The drive test start voltage is 3.98V, which maintains the initial value of 90. /. The above brightness time is 101 hours. [Example 1 Force &lt; Element for using compound (M4_16) for electron transport layer&gt; An organic EL element was obtained by the method according to Example 5, except that the compound (MM) was replaced with the compound (1-14-16). Using an IT crucible electrode as an anode and a magnesium/silver electrode as a cathode, the test was driven by a constant current using a current density of 2000 cd/m2 for an initial luminance. The driving test start voltage was 4.25 V, and the brightness of 90% or more of the initial value was maintained for 70 hours. [Example 18] &lt;Component for using compound (1-14-18) for electron transport layer&gt; An organic EL was obtained by the method according to Example 5 except that the compound (MM) was changed to the compound (Μ4·18). element. Using a ruthenium electrode as the anode &apos;secret/silver electrode as the cathode, the current scale test was practiced by obtaining a current density of 2 cd/m2 for initial production. The drive start voltage was 3.75 V, and the brightness between the initial value of 9〇% or more was 125 hours. Further [Example 19] <Element for using the compound (1 to 14-2G) for the electron transport layer> An organic EL device was obtained by the method of Example 5 except that the compound (1) (4) was replaced with the compound (Μ4-20). Taking Ιτ〇 as the anode 'with the Μ/silver electrode as the cathode' by obtaining the initial brightness

S 130 201226394 -TV*/ 2〇00 cd/m2 current density and a strange current drive test was performed. The drive test start voltage was 4.19 V ′ and the brightness between the 嶋 or more of the initial value was 63 hours. [Example 20] <Element for using the compound (1-11-18) for the electron transport layer> An organic EL was obtained by the method according to Example 5 except that the compound (1-11-1) was replaced with the compound (MM8). element. A constant current driving test was carried out by using an IT crucible electrode as an anode and a magnesium/silver electrode as a cathode to obtain a current density of an initial luminance of 2000 cd/m2. The drive test start voltage was 4.29 V, and the brightness of the initial value of 9〇% or more was maintained for 60 hours. [Comparative Example 3] An organic EL device was obtained by the method according to Example 5, except that the compound (M1-?) was changed to the compound (G). A constant current drive test was carried out by using an ITO electrode as an anode and a magnesium/silver electrode as a cathode to obtain a current density of an initial luminance of 2 〇〇〇 c d/m 2 . As a result, the driving test start voltage was 5.36 V, and the time for maintaining the brightness of 90% or more of the initial value was 2 hours. [Comparative Example 4] An organic EL device was obtained by the method according to Example 5, except that the compound (1-11-1) was replaced by the compound (H). The ITO electrode was used as the anode, and the town/silver electrode was used as the cathode, and the strange current driving test was carried out by obtaining the current density of the initial luminance of 2 〇〇〇 cd/m 2 . As a result, the driving test start voltage was 4.12 V, and the time for maintaining the brightness of 90% or more of the initial value was 26 hours. 131 201226394 40550pif [Comparative Example 5] An organic EL device was obtained by the method according to Example 5 except that the compound (1-11-1) was replaced with the compound (I). A constant current driving test was carried out by using an ITO electrode as an anode and a magnesium/silver electrode as a cathode to obtain a current density of an initial luminance of 2000 cd/m2. As a result, the driving test start voltage was 4.15 V, and the time for maintaining the brightness of 90% or more of the initial value was 30 hours. The above results are summarized in Table 4.

Table 4 Time (hours) at which the electron transport layer maintains more than 90% of the initial value. Starting voltage (V) Example 5 1-11-1 87 4.00 Example 6 1-11-2 85 4.12 Example 7 1-11-3 97 3.78 Example 8 1-11-4 83 3.95 Example 9 1-11-5 93 3.88 Example 10 1-11-39 74 4.16 Example 11 1-14-2 76 3.61 Example 12 1-14-3 141 3.85 Example 13 1- 14-11 162 4.16 Example 14 1-14-12 75 3.87 Example 15 1-14-14 227 3.82 Example 16 1-14-15 101 3.98 Example 17 1-14-16 70 4.25 Example 18 1-14-18 125 3.75 Example 19 1-14-20 63 4.19 Example 20 1-11-18 60 4.29 Comparative Example 3 G 2 5.36 Comparative Example 4 Η 26 4.12 Comparative Example 5 I 30 4.15 132 201226394 40550pif [Industrial Applicability] According to the present invention In a preferred embodiment, an organic electroluminescence device which is excellent in balance between the driving voltage and the display device, and an illumination device including the same can be provided. [Simple description of the diagram] None. [Main component symbol description] No 0 133

Claims (2)

201226394 VII. Patent application scope: 1. A compound represented by the following formula (1), Py is independently a group represented by the formula (2), (3) or (4); -0 〇 (2) (3) (4) 111 and η are 〇 or 1, m + n = l; and, # ϋ Ϊ At least one hydrogen on the benzene ring, the naphthalene ring and the pyridine ring in (^) is taken as an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms. For example, the compound described in the first paragraph of the patent application, the bean is represented by the following formula (Ul) or (1·2), ~ (1-1) Py (1-2) 201226394 40550pif In the formulas (1-1) and (1-2), py is a group represented by the formula (2), (3) or (4); -0 (2) (3) (4) 'And, at least one hydrogen of the benzene ring, the naphthalene ring and the benzene of the formulae (1-1) and (1-2) is substituted with a cycloalkane having a carbon number of 1 to 6 or a carbon number of 3 to 6. base. ‘3. The compound according to claim 1, which is represented by the following formula (1-3), (1_4), (1-5), or (1-6), In the formulae (1-3) to (1-6), Py is a group represented by the formula (2), (3) or (4); it; 135 201226394 40550pif ~U (2) (3) (4) The at least one hydrogen on the benzene ring, the naphthalene ring and the acridine ring in the formulae (1-3) to (1-6) is substituted with an alkyl group having 1 to 6 carbon atoms or a ring having 3 to 6 carbon atoms. alkyl. 4. The compound according to claim 1, which is represented by the following formula (1-7) or (1-8), In the formulae (1-7) and (1-8), Py is a group represented by the formula (2), (3) or (4); (2) (3) (4) R is a burnt group having a slave number of 1 to 6 or The carbon number is 3 to 6 ring alkyl groups, and P is an integer of 1 to 5. 5. If the compound described in claim 1 is applied, the following formula 136 201226394 HU33Upif (1-9) or (1-10) indicates that In the formulae (1-9) and (1_1〇), ΡΥ is a group represented by the formula (2), (3) or (4); (2) 0) ^4) R is an inverse of the stone i to 6 A cyclyl group or a cycloalkyl group having a carbon number of 3 to 6, and i 5 q is an integer of 1 to 5. A compound according to claim 1, which is represented by the following formula (1-11) or (1-12). In the formulae (K11) and (1-12), 137 201226394 40550pif Py is a group represented by the formula (2'), (3') or (4'); In the mountains (1), (3), and (4), 'R is an alkyl group having an alkyl group of i to 6 in an inverse number of 3 to 6; and s is an integer of 1 to 4. 7. The compound according to claim 1, which is represented by the following formula (M3) or (1-14), In the formulae (M3) and (1-14), a group represented by the formula (2,), (3,) or (4,); In 2 (2), (3,) or (4,), R is an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms; and s is an integer of 1 to 4. The compound of claim 1, which is represented by the following formula 138 201226394 4U55Upif (1-15) or (i_l6), A group represented by the formula (2), (1) or (4); (2) (3) (4) and t is an integer of 1 to 4. 1 2 6 such as the compound of the first item of the patent scope of Shen 2, which is based on the following formula The compound of the first formula of the formula 2, which is as follows 139 201226394 h-uj jupif (1-7-74) 11. The compound according to claim 1, which is represented by the following formula (1-7-98) (1-7-98) 12. The compound according to claim 1, which is represented by the following formula (1-7-96) (1-7-96) 13. The compound according to claim 1, which is represented by the following formula (1-14-14) (1-14-14) S 140 201226394 4U550pif 14. The compound according to claim 1, which has the following formulas (1-11-1), (1-11-2), (1-11- 3), (1-11-4), (1-11-5), (1-11-6), (1-11-8), (1-11-18), (1-11-39) , (1-14-2), (1-14-3), (1-14-11), (1-14-12), (1-14-13), (1-14-15), ( Any of 1-14-16), (1-14-17), (1-14-18), and (1-14-20) means: 141 201226394 40550pif 15. An electron transporting material comprising a compound according to any one of claims 1 to 14. S 142 201226394 40550pif 16. An organic electroluminescent device comprising: a pair of electrodes including an anode and a cathode; a light-emitting layer disposed between the pair of electrodes; and disposed between the cathode and the light-emitting layer An electron transport layer and/or an electron injection layer containing the electron transport material of claim 15 of the patent application. 17. The organic electroluminescent device of claim 16, wherein at least one of the electron transport layer and the electron injecting layer further comprises a metal porphyrin metal complex, At least one of a group consisting of a bipyridine derivative, a morphine derivative, and a borane derivative. 18. The organic electroluminescent device of claim 16, wherein at least one of the electron transport layer and the electron injecting layer further comprises an alkali metal, an alkaline earth metal, a rare earth metal. , an oxide of an ferrous metal, a halide of an alkali metal, an oxide of an alkaline earth metal, a compound of a smectite metal, an oxide of a rare earth metal, a halide of a rare earth metal, an organic complex of an alkali metal, or an organic earth metal At least one of a group consisting of a complex compound and an organic complex of rare earth gold. 143 201226394τ •----χΉ IV. Designated representative map: (1) The representative representative of the case is: None. (2) A brief description of the component symbols of this 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: 3 201226394 is the first Chinese version of the 1*ί) 014〇164. There is no slash correction. The date of this amendment is: March 1, 101 invention patent description. (The format and order of this manual, please do not change it. ※Do not fill in the mark ※Application number: ※Application曰: ※Working PC classification: 1. Inventor name: (Chinese/English), electronic transmission material and organic electroluminescent device using it ELECTRON TRANSPORT MATERIAL AND ORGANIC electroluminescent device using ❹ THE SAME II Abstract: The compound represented by the formula (1) of the present invention is an electron transporting material used as an organic EL element, which contributes to the life extension of the organic EL element by using the electron transporting material. In A (1), 'py is independently a group represented by formula (2), (3) or (4); m and n are 0 or 1 'm + n= 1 ; and, in the formula (1), the benzene ring, naphthalene 201226394 is the 100140140 Chinese manual without a slash correction. Amendment date: 1〇1年月月j日六BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel electric material having a (four) group, and an organic electroluminescent device using the electron transporting material (hereinafter referred to as an organic EL element hereinafter, or simply For components) and so on. [Previous Technology] In recent years, the EL element has attracted attention from the full color flat panel display, and the industry is currently researching it. In order to promote the practical use of organic EL elements, the driving voltage is reduced, and the life delay is indispensable. In order to = these elements, the industry is developing new electronic transmission materials. In particular, it is necessary to reduce the driving voltage of the blue element and extend the life. In the case of using a 2,2'-bipyridyl compound as a phenamhroline derivative or the like, an electron transporting material is described in the patent document: (Patent No. 2003-123983). The organic EL element can be driven at a low voltage. However, the element characteristics (driving voltage, luminous efficiency, etc.) reported by the examples of this document are only relative values based on comparative examples, and actual measured values which can be judged to be practical values are not described. Further, an example in which a 2,2,-bipyridyl compound is used for an electron transporting material is disclosed in Proceedings of the 10 International Workshop on Inorganic and Organic Electroluminescence, the 10th International Symposium on Inorganic and Organic Electroluminescence. Patent Document 2 (Japanese Patent Laid-Open Publication No. 2002-158093) and Patent Document 3 (International Publication No. 2007/86552) disclose. The compound described in Non-Patent Document i 201226394 • v w t i Date of revision: March 1, 101 The Chinese manual No. 100, IMOMO 64, has no T-line correction and is not practical. Although the compound described in Patent Document 2 and Patent Document 3 can drive the organic EL element at a relatively low voltage, it is expected to further extend the life in practical use. [Prior Technical Literature] [Patent Literature] [Patent Document 1] Japanese Laid-Open Patent Publication No. 2003-123983 [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] l]Pr〇CeedingS 〇f the l〇th Internati〇nal Workshop 〇n Inorganic and 〇rganic La (10) Her Blood Succession (2000) (The 10th Inorganic and Organic Electroluminescence International (2000)) [Summary] Too much research on the problems of this prior art. The topic of Haoyue is to provide a material that contributes to the life extension of organic EL components. 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 diligently studied, and the compound is used for electron transport of an organic element: an organic EL element driven by a sequel, and the H-specific f/, can be obtained as a naphthyl group or a phenyl group capable of long-lived onion. - (2-naphthyl) phenyl, such as a phenyl group, and a benzene ring, a naphthalene ring, and 2 = Zhao, a fluorenyl group, or at least one of a carbon or a carbon number of 丨 6 6 Hydrogen is taken from the compound of the 3 to 6 cycloalkyl group of the horse 201226394 ίί 7ί) ΐΐ 40164 Chinese manual without a slash correction This correction date: 1 March 1st, 1st, based on this discovery completed the present invention. The above problems are solved by the items shown below. [1] A compound represented by the following formula (1), (1) In the formula (1), Py is independently a group represented by the formula (2), (3) or (4); m and η are 0 or 1, m + n = 1; and at least one hydrogen on the benzene ring, the naphthalene ring and the pyridine ring in the formula (1) is substituted with an alkyl group having 1 to 6 carbon atoms or a carbon number It is a 3 to 6 cycloalkyl group. [2] The compound according to the above [1], which is represented by the following formula (1-1) or (1-2), (1-1) Py (1-2) 201226394A Date of revision: March 2011 Γ〇 014 164 Chinese manual without reticle correction In this formula (1-1) and (1-2), Py is the formula ( a base represented by 2), (3) or (4); And the benzene ring, the naphthalene ring and the 5-to-hydrogen on the bite ring in the formulae (M) and (b) are substituted with a carbon group having a carbon number of 丨6 or a ring having a carbon number of 3 to 6. alkyl. [3] The compound according to the above [1], which is represented by the following formula (u), (1-4), (1-5), or (1-6), In the formulae (1-3) to (1-6), Py is a group represented by the formula (2), (3) or (4); (2) 201226394 Amendment date: March 30 of the following year is the Chinese manual of No. 100140164 without a slash correction and on the benzene ring, naphthalene ring and pyridine ring in '(1-3)~(1-6) At least one hydrogen is substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms. [4] The compound according to the above [1], which is represented by the following formula (丨_7) or (丨_8), In the formulae (1-7) and (1-8), Py is a group represented by the formula (2), (3) or (4); and -0 is 0 (2) (3) R is an alkyl group having a % of from 1 to 6 or a cycloalkyl group having a carbon number of from 3 to 6 and an integer of from 1 to 5 represented by the following formula (1-9) or P. [5] The compound d-ιο) as described in the above [1], 201226394 Revision date: On March 1st, 1st, the lOGUGl64 mid-faced ducks will be corrected in this formula (1_9) and (1-10), Py is the formula (2), (3) or (4) Base of representation; R is an alkyl group having a carbon number of 1 to fluorene or a cycloalkyl group having a carbon number of 3 to 6; and q is an integer of 1 to 5. [6] The compound according to the above [nth item, which is represented by the following formula (in) or (1-12), In formula (m) and (1-12), Py1 is a group represented by formula (2,), (3,) or (4) In the formulas (2'), 〇·) and (4,), the ruler is a burnt group with a carbon number of 6 or 9 201226394 is the 100th M0164 Chinese manual without a slash correction. Amendment date: March 1st, 10th a cycloalkyl group having a carbon number of 3 to 6; and s is an integer of 1 to 4. [7] The compound according to the above [1], which is represented by the following formula (M3) or (1-14), In the formulae (1-13) and (1-14), Py1 is a group represented by the formula (2'), (3,) or (4,); In the formula (2'), (3,) or (4'), 'R is an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms; and, s is an integer of 丨4 to 4 . [8] The compound according to the above [丨], which is represented by the following formula (1-15) or (M6), 10 201226394 _____—丄 is the Chinese manual No. 100140164. There is no slash correction. The date of this amendment is: in the formula (1-15) and (1-16) of March 1st, 1st, Py is the formula (2), (3). Or the base represented by (4); R is an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms; and t is an integer of 1 to 4. [9] The compound according to [1] above, which is represented by the following formula (1-7-26) [10] The compound according to the above [1], which is represented by the following formula (1-7-74) [11] The compound according to the above [1], which is represented by the following formula (1-7-98) 11 201226394 HK) DD\ipiil is the 100th HO 164 Chinese manual without a slash correction Amendment date: March 1, 1st, 1st (1-7-98) [12] The compound as described in the above [1], which is represented by the following formula (1-7-96) (1-7-96) [13] The compound as described in the above [1], which is represented by the following formula (1-14-14) (1-14-14) [14] The compound according to the above [1], which is represented by the following formulas (1-11-1), (1-11-2), (I-11-3), ( M1_4), ( 1-11'5) (1-11-6) ' ( 1-11-8) ^ ( Ml&quot;18) ' ( 1-H-39) &gt; ( 1-14^) 12 201226394 I Vy w» \_/^/士士&quot;1 For the Chinese manual No. 10014〇164, there is no slash correction. The date of this amendment: March 1, 101 (1-14-3), (1-14-11), (1-14-12), (1-14-13), (1-14-15), (M4-16), (1-14-17), (1-14-18), and (1- Any one of 14-20) 13 201226394 4-UOJUpiil is the Chinese manual of No. 100140164 without a slash correction. Amendment date: March 1st, HH [15] An electron transporting material, which contains any of the above [1] to [14], 14 201226394, and the Chinese specification of No. 100140164, which is not underlined. This revision date is as described in the March 1, 2011 issue. Compound. [16] 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; and a cathode disposed between the cathode and the light-emitting layer and containing the above The electron transport layer and/or the electron injection layer of the electron transport material according to [15]. The organic electroluminescent device according to the above [16], wherein at least one of the upper electron transporting layer and the electron injecting layer further comprises a hydroxy phthalocyanine metal complex, a bipyridine derivative, At least one of the group consisting of a phenanthroline derivative and a borane derivative. [18] The organic electroluminescent device according to the above [16] or [17] wherein at least one of the electron transport layer and the electron injecting layer further comprises an oxidation selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, and alkali metals. Toothing of alkali and alkali metal, oxide of soil test metal, halide of soil test metal, oxide of rare earth metal, halide of rare earth metal, organic complex of metal test, organic complex of metal And at least one of the group consisting of organic complexes of rare earth metals. [Effects of the Invention] Further, the present compound is stable even when a voltage is applied in a film state, and is: The present TM^ compound is used for electrical power of aeronautical components. By obtaining the EL element having the longevity phase and the gas injection layer of the present invention, it is possible to produce a cow. By using the present invention, there is a high performance display device in which Wang Caijiu has a shoulder. 15 201226394 wroupiri is the Chinese manual of No. 100140164 without a slash correction. Amendment date: March 1, 101. The following is a more detailed description of the present invention. In the present specification, for example, "the compound represented by the formula (1-7-26)" may be referred to as "the compound (1-7-26)". The compound represented by the formula (1-7-74) is sometimes referred to as "compound (1-7-74)". The symbols and formulas of other formulas are also the same. &lt;Description of the Compound&gt; The first invention of the present invention is a compound having a pyridyl group, a bipyridyl group or a pyridylphenyl group represented by the following formula (〇). (2) (3) (4) In the formula (1), 'Py is independent, and f and n represented by the formula (2), (3) or (4) are 〇 or 丨, and m + n = =1. Further, at least one hydrogen on the benzene ring or the naphthalene ring in the formula (丨) is substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms. 4匕, the pyridyl group represented is specifically a 2-pyridyl group, a 3-pyridyl group, or the bi-pyridyl group represented by the formula (3) is specifically 2,2,-bipyridyl-5-yl, _ton °定定,2,2'-联" ratio α定-4-yl, 2,3'-linked π than 唆_5_ base, 2,3,_ 疋6 base, 2,3'-combination ratio _4_基,2,4'- 〇 〇 5 5 5 5 5 5 5 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 2012 0--6-yl, 2,4'-linked β is more than α-1,4-yl, 3,2'-linked n-bite-6-yl, 3,2,-bi-pyridyl-6-yl, 3 , 4'-bipyridyl-5-yl, 4,2'-bipyridin-3-yl, 4,3,-bipyridin-3-yl, or 4,4^biindole-3-yl. The η-pyridyl group represented by the formula (4) is specifically 4—(2-acridinyl)phenyl, 4-0 pyridyl)phenyl, 4-(4-pyridyl)phenyl, 3-(2- Pyridyl)phenyl, 3-(3-acridinyl)phenyl, 3-(4-pyridyl)phenyl, 2-(2-pyridyl)phenyl, 2-indolyl)phenyl , or 2 · (4_β than bite base) stupid base. In the formula (1), the position at which Py is bonded may be any position on the stupid group or the 2-naphthyl group, preferably 4 positions and 3 positions on the phenyl group, and preferably 6 positions on the 2-naphthyl group. And 7 digits. In terms of not expanding the conjugate system, and not reducing the LUm 〇 (lowest unoccupied molecular orbita, the lowest unoccupied molecular orbital energy level is particularly preferred as the phenyl group. In addition, in terms of easy availability of raw materials, More preferably, it is a 6-naphthyl group. The benzene ring, the naphthalene ring, and the pyridine ring in the formula (1) are exemplified by an alkyl group having 1 to 6 carbon atoms: an anthracene group, an ethyl group, and a positive group. Propyl, isopropyl n-butyl f, isobutyl, tert-butyl, n-pentyl, isopentyl, 2,2-dimethyl = earth, n-hexyl, and isohexyl. Among them, preferred alkyl groups The methyl group, the ethyl group, the propyl group, and the third butyl group are more preferably a methyl group and a third butyl group. Examples of the peach group having a carbon number of 3: a cyclopropyl group, a cyclobutyl group, and a cyclopentyl group. Cyclohexyl. ^ Ϊ Considering the availability of the catalyst and the ease of synthesis, the preferred % alkyl group is a cyclohexyl group. (1-1) or (1-2) Formula (the compound represented by υ is specifically The compound represented by the formula. 17 201226394 υ υ υ ι ι ι ι ι ΐ ΐ 第 140 140 140 140 140 140 140 140 140 Revision date: March 1, 1st The Py mosquito meanings in the formulas (1_1) and (1.2) are the same as described above. More specifically, the compound represented by the formula (1) is a compound represented by any one of the following formulas (1-6). The definition of π ry is the same as that of the compound represented by the formula (1) in the above iiiU day η. A compound represented by any one of them. )~(1- 18 201226394 Revision date: March 1, 1st, 1st, HUJJUpill is the 100M0164 Chinese manual without a line revision The definitions of Py&amp;R in the formulae (1-7) to (1-10) are the same as described above. P in the formulae (1-7) and (1-8) is an integer of 1 to 5, preferably an integer of i to 2, more preferably 1. The position of the phenyl group substituted by R is not limited, and is preferably 3 or 4 positions. q in the formulae 0-9) and (M0) is an integer of 5, preferably an integer of 1 to 2, more preferably! . The position of the naphthyl group substituted by R is not limited, and is preferably 6 or 7 positions. Further, the compound represented by the formula (1) is more specifically a compound represented by any one of the following formulas (M1) to (1-14). 19 201226394 Chinese manual no face correction ^UD^upirl is the position of the integer group of the formula (2') and 1-4 of the formula (1), and the compound represented by the formula (1) is more specifically the following formula ( 1-15) or a compound represented by (1-16). The definitions of Py&amp;R in the formulae (M5) and (1-16) are the same as described above. t is an integer of 1 to 4, preferably 1 or 2, more preferably 1. The position at which the phenyl group is substituted by the ruthenium is not limited, and in consideration of the ease of synthesis, in the case of a 1,4 phenylene group, it is preferably 3 positions based on the carbon bonded to ruthenium. In the case of a 1,3-phenylene group, it is preferably 4 based on the carbon bonded to the hydrazine. Specifically, the compound represented by the above formula Q) is roughly classified into the formula (17) to (1-16). ) the compound represented. Among these, preferred structures are the formula (1-7), the formulae (1-9) to (i_U), and the formula (I1) to (M6), and the more preferable structure is the formula (1-7). &lt;Specific Example of Compound&gt; Specific examples of the compound of the present invention can be disclosed as the following formulas, but the present invention is not limited to the disclosure of these specific structures. 20 201226394n i "U64 Chinese manual without sizing correction. This correction date: (8) The following is a specific example of the compound represented by the formula (1-7); the compound represented by the formula (1-7) Specifically, for example, the following formula (^7-144) is shown. Among these, preferred compounds are of the formula (I-,)) 1-7-6) '^C(1-7-10)~( 1 -7-12 )&gt; ^( 1-7-16)^( 1-7-30)' Formula (1-7-34)~(1-7-36), Formula (1-7-40)~ (uw), formula (1-7-73)~(1-7-78), formula (1_7_82)~(1·7_84), formula (1_7_88)~(1-7-102), formula~(1_7_1〇 8) and (um) ~ (Bu 7-120). (1-7-9) 21 201226394^υ^^υρπΐ Revision date: 1〇1年1月1曰 For the 100140164 Chinese manual, no underline correction (1-7-11) (1-7-17) 1. 22 201226394 H-UJJUpifl Revision date: March 1, 1st, 1st Chinese version of the 100140164 no-line revision 23 201226394 wroupnl Revision date: March 1, 1st is the Chinese manual of No. 100140164 without a slash correction -7-34) 24 201226394 H-VJJJVjpifl Revision date: March 1st, 1st, 1st Chinese version of No. 100140164 No underline correction 〇 ❹ 25 201226394 4U!)5Upitl is the Chinese manual of No. 100140164 without a slash correction. Amendment date: March 1, 1st, 1st 26 201226394 4U55Upitl Correction period: March 1st, 1st, 1st, 1st, 100th, 140th Chinese manual, no underline revision 27 201226394 JUpul is the Chinese manual for the 100140164 without a slash correction. Amendment date: March 1, 1st, 1st 28 201226394 4U55Upifl No Chinese painting for the 100140164 Chinese manual! J line correction this revision date: March 1, 1 year 29 201226394 4U!)!)Upiil is the Chinese manual of the 100140164 without a slash correction 201226394 is the Chinese manual of No. 100140164 without a slash correction. Amendment date: March 1, 1st, 1st ❹ 31 201226394 40550pifl For the Chinese manual No. 100140164, there is no slash correction. Amendment date: March 1, 1st, 1st 32 201226394 ^u^^upifl is the Chinese manual of No. 100140164. There is no slash correction. This revision date: March 1, 1st, 1st &lt;Specific example of the compound represented by formula (1-8) &gt; Specific examples of the compound represented by the following formula (1-8-1) to (1-8-105) are shown. 33 201226394 JUpiil is the Chinese manual for the 100140164 without a slash correction. Amendment date: March 1, 1st, 1st 34 201226394 4U33Upill is the Chinese manual for the 100140164 without a slash correction. Amendment date: March 1, 1 year 〇 35 201226394 40550pifl For the Chinese manual No. 100140164, there is no slash correction. Amendment date: March 1, 1st, 1st 36 201226394 4U^DUpifl is the Chinese manual of No. 100140164 without a slash correction. Amendment date: March 1, 1 year ❹ 37 201226394 40550pifl For the 100th Chinese manual of the IOOHOI64, there is no slash correction. Revision date: March 1, 1st 38 201226394 • V/ ^ ^ ΧΛ. X is the Chinese manual of No. 100140164 without a slash correction. Revision date: March 1, 1 ❹ ❹ 39 201226394 4U5DUpill is the Chinese manual for the 100140164 without a slash correction. Date of revision: March 1st of the year 40 201226394 For the Chinese manual No. 100140164, there is no slash correction. Amendment date: March 1, 1st, 1st 41 201226394 4Ui)i) Upitl is the Chinese manual of No. 100140164 without a slash correction. Amendment date: March 1, 101 &lt;Specific Example of the Compound of the Formula (1-9)&gt; The compound represented by the formula (1-9) is specifically shown, for example, in the following formula (b-9-48). Among these, preferred compounds are rabbits 9 1 ) ~ (1-9-12 ), ( 1-9-16) ~ (1-9-18 ), formula (recognition (4) and formula (Bu 9-40) ~(ι·9_42). Κ9·36) 42 201226394 ^UDOUpill For the Chinese manual No. 100140164, there is no slash correction. This revision date: l〇i year March 1 ❹ 43 201226394 is the Chinese manual of the 100140164 without a slash correction (1-9-10) (1-9-12) (1-9-14) (1-9-16) (1-9-18) (1-9-20) Revision date: 1〇1年3 Month 1 (1-9-19) (1-9-21) (1-9-22) (1-9-24) (1-9-23) 44 201226394 4U55Upifl Revision date: March 1st of the following year No. 100140164 Chinese manual without line correction 45 201226394 40550pifl For the Chinese manual No. 100140164, there is no slash correction. Amendment date: March 1, 1st, 1st (1-9-35) (1-9-37) (1-9-39) (1-9-41) (1-9-42) (1-9-43) (1-9-44) (1-9-45) 46 201226394 4U55Upifl is the Chinese manual of No. 100140164. There is no slash correction. The date of this revision is: 1. The specific example of the compound represented by the formula (1-10) is represented by the formula (1-10). Specific examples of the compound are shown by the following formula (1-10-1) to (1-10-48). Among these, preferred compounds are the formulae (1-10-1) to (1-10-6), (1-10-10) to (1-10-12) and (1-10-16)~ (1-10-21). 47 201226394 Revision date: 1〇1月1月1350550pifl is the 100140140 Chinese manual without a slash correction (1-10-21) (1-10-23) 48 201226394 —ν/^/ιχ'Ί For the Chinese manual No. 100140164, there is no slash correction. Amendment date: March 1, 1st, 1st (1-10-26) (1-10-28) (1-10-30) (1-10-32) 49 201226394 40550pitl is the Chinese manual of No. 100140164 without a slash correction (1-10-36) (1-10-38) (1-10-40) (1-10-42) (1-10-43) (1-10-45) Revision date: 1〇1年3 January 1 (1-10-34) (1-10-47) 50 201226394 4U5^Upltl is the Chinese manual of No. 100140164. There is no slash correction. The date of this correction is: March 1, 1st, 1st &lt;Specific Example of Compound represented by Formula (1-11) > Formula (1-11) Specific examples of the compound to be represented are shown by the following formula (1-11-1) to (1-11-60). Among these, preferred compounds are the formulae (1-11-3) to (1-11-10), (1-11-25) to (1-11-28) and (1-11-51)~ (1-11-60). 51 201226394 40550pifl is the Chinese manual of the 100M0164 without a slash correction. Date of revision: March 1, 101 52 201226394 4U55Upitl is the Chinese manual of No. 100140164 without a slash correction. Amendment date: March 1, 1st, 1st 53 201226394 JUpXll is the Chinese manual for the 100140164 without a slash correction. Date of revision: March 1, 1st, 1st (1-11-41) (1-11-45) (1-11-47) (1-11-49) (1-11-43) (1-11-46) (1-11-48) (1-11-50) (1-11-51) (1-11-53) (1-11-52) (1-11-54) 54 201226394 4υ"υριί1 is the 10014014 Chinese manual without a slash correction. Amendment date: March 1, 1st, 1st &lt;Specific example of the compound represented by the formula (1-12)&gt; Specific examples of the compound represented by the formula (1-12) are shown by the following formula (1-12-1) to (1-12-60). . 55 201226394 40550pin is the Chinese manual of the 100140164 without a slash correction. Amendment date: March 1, 1st, 1st (1-12-1) (1-12-3) (1-12-5) (1-12-7) (1-12-9) (1-12-2) (1-12-6) (1-12-8) (1-12-10) (1-12-4) 56 201226394 4U550pifl is the Chinese manual of No. 100140164 without a slash correction. This revision date: 1〇1年3 Month 1 (1-12-12) (1-12-14) (1-12-16) (1-12-18) (1-12-20) 〇 (1-12-22) (1-12-24) 57 201226394 Revision date: 1〇1月1月1350550pifl is the 100140140 Chinese manual without a slash correction (1-12-25) (1-12-33) (1-12-34) (1-12-35) (1-12-36) (1-12-37) (1-11-38) 58 "1 201226394 Revision date: March 1 of the following year is the Chinese manual of No. 100140164 without a slash correction (1-12-40) (1-12-42) (1-12-43) (1-12-45) (1-12-44) (1-12-46) (1-12-47) ❹ (1-12-49) (1-12-48) (1-12-50) (1-12-51) (1-12-52) (1-12-53) (1-12-54) 59 201226394 40550pifl For the Chinese manual No. 100140164, there is no slash correction. Amendment date: March 1, 1st, 1st (1-12-58) &lt;Specific example of the compound represented by the formula (1-13)&gt; Specific examples of the compound represented by the formula (1-13) are shown by the following formula (1-13-1) to (1-13-60). . Among these, preferred compounds are the formulae (1-13-21) to (1-13-28) and the formula (1-13-31) to (1-31-40). 60 201226394 4U55Upifl is the Chinese manual of No. 100140164 without a slash correction. Amendment date: March 1, 1st, 1st (1-13-4) (1-13-6) 61 201226394 40550pifl For the Chinese manual No. 100140164, there is no slash correction. Revision date: March 1, 1st, 1st (1-13-19) (1-13-20) 62 201226394 ν/^/χ χΊ For the Chinese manual No. 100140164, there is no slash correction. Revision date: March 1, 1st, 1st 63 201226394 40550pifl For the Chinese manual No. 100140164, there is no slash correction. Amendment date: March 1, 1st, 1st 64 201226394 l ^ AX ^ is the Chinese manual of No. 100140164 without a slash correction. Amendment date: March 1, 1st, 1st &lt;Specific example of the compound represented by the formula (1-14)&gt; The specific formula of the compound represented by the formula (1-14) is, for example, the following formula (1-14-1) Ο ～ (1-14-60) Show. Among these, preferred compounds are the formulae (1-14-1) to (1-14-18). 65 201226394 40550pifl For the Chinese manual No. 100140164, there is no slash correction. Amendment date: March 1, 1st, 1st 66 201226394 4U55Upifl is the Chinese manual of No. 100140164 without a slash correction. Revision date: March 1st, 1st 67 201226394 Revision date: March 1, 101 ^iT〇^40164 Chinese manual without line correction (1-14-28) (1-14-30) 68 201226394 4tmupifl For the Chinese manual No. 100140164, there is no slash correction. Amendment date: March 1, 1st, 1st 69 201226394 40550pifl For the Chinese manual No. 100140164, there is no slash correction. Amendment date: March 1, 1st, 1st &lt;Specific example of the compound represented by the formula (1-15)&gt; Specific examples of the compound represented by the formula (1-15) are shown by the following formula (1-15-1) to (1-15-48). . Among these, preferred compounds are the formulae (1-15-10) to (1-15-12), (1-15-16) to (1-15-18), and the formula (1-15-34). ~ (1-15-36) and (1-15-40) ~ (1-15-42). 70 201226394 4055ϋριΩ is the Chinese manual of the 100140164 No-line correction. Date of revision: March 1, 1st 71 201226394 4U33Upirl is the Chinese manual of the 100140164 without a slash correction (1-15-10) (1-15-12) (1-15-14) (1-15-16) (1-15-18) Revision date: March 1st, 1st (1-15-11) (1-15-13) (1-15-15) (1-15-17) (1-15-19) (1-15-22) (1-15-24) (1-15-20) (1-15-21) (1-15-23) 72 201226394 Revision date: March 1, 1 year 4U^Upifl is the Chinese manual of No. 100140164 without a slash correction 〇 ❹ (1-15-25) (1-15-26) (1-15-28) (1-15-27) (1-15-29) (1-15-30) (1-15-31) (1-15-33) (1-15-32) 73 201226394 40550pifl For the Chinese manual No. 100140164, there is no slash correction. Amendment date: March 1, 1st, 1st &lt;Specific Example of Compound represented by Formula (1-16)&gt; Specific examples of the compound represented by Formula (1-16) are shown by the following formula (1-16-1) to (1-16-24) . Among these, preferred compounds are the formulae (1-16-1) to (1-16-5). 74 201226394 40550pifl is the Chinese manual of No. 100140164 without a slash correction (1-16-1) (1-16-3) (1-16-5) (1-16-7) (1-16-9) Revision date: March 1, 1st 75 201226394 40550pifl Revision date: March 1st, 1st, 1st Chinese version of the 100140164 no-line revision (1-16-10) 76 201226394 • W ▲ 丄 丄 中文 中文 中文 中文 中文 中文 中文 中文 中文 中文 中文 中文 中文 中文 中文 中文 中文 中文 中文 中文 中文 中文 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 The compounds of the present invention can be synthesized by a suitable combination using a general known synthetic method. <Synthesis of a compound represented by the formula (1-7-1) to the formula (1-7-144)&gt; Reaction 1 R: an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms: an integer of 1 to 5 First, a 9-phenyl group in which a phenyl group is substituted with an alkyl group (cycloalkyl group) by the reaction 1 Hey. The alkyl-substituted bromobenzene is reacted with magnesium metal in THF to prepare a Grignard reagent, which is reacted with 9-bromoindole in the presence of a catalyst to form a phenyl group through an alkyl group (ring). Alkyl) substituted 9-phenylindole. The combination of the benzene ring and the anthracene ring is not limited to the above method, and for example, a root-shore coupling reaction using a zinc complex or a eucalyptus coupling reaction using boric acid or a boric acid ester may be employed, and such conventional methods may be suitably used depending on the situation. . 77 201226394 40550pifl No Chinese Standard Specification No. 100140164 Revision Standard Revision Date: March 1, 101 Reaction 2 is the bromination of the 10-position of 9-phenylindole substituted with an alkyl group (cycloalkyl) using N-bromosuccinimide. Here, a common brominating agent other than N-bromosuccinimide can also be used. Reaction 3 is the coupling of the en ring to the naphthalene ring. Firstly, according to the conventional method, 2_ shoulder and 6-methoxynaphthalene are made into a Grignard reagent, and the 9_(tetra) derivative synthesized by the disk 2 is reacted in the presence of a catalyst to synthesize 9_(6_?oxycai-2_ = a 10-benzene derivative. In the same manner as the reaction oxime, the benzene ring and the onion ring are entangled in the above method, and for example, a root bank meal using a zinc complex or a sirring ring can be used, which is suitable according to the situation. Use these conventional methods. Urine 78 201226394 40550pifl No. 100140164 Chinese manual without line correction This reaction 4 Revision date: March 1, 1 year Reaction 4 is a dehydration group of a 9-(6-nonylnaphthalen-2-yl)-10-phenylindole derivative to form a naphthol. Here, a reagent which is usually used for the demethylation reaction can also be suitably used. Reaction 5 Reaction 5 is the conversion of -OH of naphthol to triflate. The -OTf in the reaction formula is an abbreviation of -0S02CF3. Reaction 6 Br · HCI i-PrMgCl i-PrMgCl ZnCl2 . TMEDA THF Reaction 6 is to make n ratio bite by the Negishi coupling reaction. 201226394 40550pifl is the 100th Chinese manual. There is no underline correction. Amendment date: March 1, 101. % is combined with naphthalene ring. First, 4-bromopyridine was made into a Grignard reagent. Here, since 4-bromopyridinium hydrochloride which is stable to the raw material is used, 2-fold molar isopropylmagnesium chloride is used, but it is also possible to use a salt which is not necessary to use a hydrochloride. To the Grignard reagent, a zinc chloride complex is synthesized by chlorination, and the target is synthesized by palladium-contacting the phthalate reaction. f should be 1 厗 coupling The reaction _ can also be suitably used for the Suzuf Pllng reverse coupling reaction. In the case of the sapling coupling reaction, the most suitable sputum can be prepared according to the target, for example, the following reaction can be used. The boric acid vinegar shown in 7 is used to obtain the target. As a specific example of the hammer catalyst used in the coupling reaction, the standard is from 2, 2 (2), 2, 2, 2, 2, 2, 2, 2, 2, 2012, 3, No slash correction This correction earns 1 3 1 year March! Daily saturate (0), two (one subunit ketone) two (〇) gas-like complex, bis(dibenzylideneacetone) palladium (0 , bis(tris-tert-butylphosphino)palladium (ruthenium), or (丨屮·bis(diphenylphosphino)ferrocene) di-palladium (11). In addition, in order to promote the reaction, it is also visible. In the case, a phosphine compound is added to the palladium compound. Specific examples of the phosphine compound include tri(t-butyl)phosphine, tricyclohexylphosphine, and μ(Ν,Ν_:nonylaminoindenyl). _2_(di-t-butylphosphino)ferrocene, 1-(anthracene, Ν•dibutylaminoindenyl)_2_(di-tert-butylphosphonyl)ferrocene, 1-(methoxy Mercapto)-2-(di-t-butylphosphino)ferrocene 1'1-bis(a second butyl group) ferrocene, 2,2'-bis(di-t-butylphosphino) )-l,r-binaphthyl, 2-methoxy-2-, di-tert-butylphosphino)", lenidine, or 2-dicyclohexylphosphino-2,6,_2 Specific examples of the base used for the reaction include sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogencarbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium ethoxide, and third butanol. Sodium, sodium acetate, tripotassium phosphate or potassium fluoride. Specific examples of the solvent to be used in the reaction include benzene, r-benzene, diphenylbenzene, L2,4·trimethylbenzene, and ν. ν-Dimercaptoamine, tetrahydrofuran, diethyl ether, tert-butyl methyl ether, L4-dioxane, decyl alcohol, ethanol, cyclopentyl decyl ether or isopropanol. These solvents are suitable for selection. It can be used alone or as a mixed solvent. <Synthesis method of the compound represented by the formula (1-8-1) to the formula (1-8-105)> In the above reaction 3, if 2 is used _Bromo-7-methoxynaphthalene can be synthesized in the same manner as 2-bromo-6-methoxynaphthalene. <Formula (1-9-1)~Formula (1-9-48) and Formula (im) ～式(L48) 81 201226394 40550pifi is the Chinese manual of the 100140164 No-line correction. The date of this correction: the synthesis method of the compound represented by the March i day of 1〇1 By using these benzene skeletons and the raw materials substituted by the Cai skeleton, the raw materials used in the reaction 1 to the reaction 3 can be used in the same manner as described above. That is, the 2-bromofluorene Grignard reagent and 9-bromine are used.蒽 Coupling, bromination of the 10th position of the oxime according to = 2, and then reacting the bromide with the Grignard reagent of the methoxy bromobenzene methoxy benzene to obtain 9_(4_ or 3_methoxy) Phenyl)-10-(2-naphthyl)anthracene. For the compound, the demethylation of the methoxy group may be carried out in the following order. Further, in addition to the specifically exemplified compound, it is of course possible to carry out the synthesis according to the above synthesis method by suitably using a raw material according to the target. <Formula (1-11-1)~Formula (1-11-60), Formula (i-12-1)~Formula (1-12-60), Formula dm)~Formula (μμο) and Formula (M4 i a method for synthesizing a compound represented by the formula (1-14-60)&gt; by using an alkyl group or a cycloalkyl-substituted pyridine derivative in place of the above-mentioned reaction 6 or the raw material used in the reaction 7 The material can be synthesized in the same manner as described above as a raw material. The pyridine derivative substituted with an alkyl group or a cycloalkyl group can be synthesized as shown in the following Reaction 8 to Reaction 9. Here, although a method of synthesizing a pyridine moiety in a compound represented by the formula (1-11-11), the formula (1-12-11), the formula (wm), and the formula (Bu 14-11) is exemplified, By appropriately changing the starting materials, it is possible to synthesize various ratios of sigma derivatives which are substituted by a cyclic group or a cycloalkyl group. 82 201226394 Revision date: March 1, 1st, 40550pifl is the Chinese manual of the 100140164 No-line correction. Reaction 8 Br Reaction 9 1) RLi or Mg or RMgX 2) ZnCI2 or ZnCI2.TMEDA ClZn Pd-catalyst &lt;Method for synthesizing a compound represented by the formula (1-15-1) to the formula (1-15-48) and the formula (1-16-24)&gt; In the above formula (1-9-1) In the step of introducing a phenyl group in the method for synthesizing a compound represented by the formula (1-9-48) and the formula U-10-1) to the formula (1_10_48), a benzene substituted with an alkyl group or a cycloalkyl group is used. The base can be. For example, the synthesis method shown in the following reaction 10 can be used. Reaction 1 〇 The definition of R in the formula is the same as described above. The target compound is only linked to the ^ ° root at any position of the benzene ring. The compound of the present invention is used for the R in the presence. In the case of a layer or an electron transport layer, the application of the electric field sub-injection indicates that the compound of the present invention is 83 as 201226394 201226394 40550pifl is the fourth round of the Chinese text book without a slash correction. This correction date: 丨0! Or excellent in electron transport materials. Here, the cathode receives electrons and injects a layer of the organic layer; the household; == means a layer for transferring the injected electrons to the light-emitting layer = and may also serve as an electron-injecting layer. The layers are used to transport layers and electron transport (4). The material is referred to as an electron injecting material &lt;Description of an organic EL element&gt; The second invention of the present invention is a driving voltage of an iEL element in which the compound represented by the formula (1) of the present invention has a == layer = Low, high durability during driving. At least the type of 'between the anode and the cathode is sandwiched between the anode and the cathode. The component has a hole-seeking layer/light-emitting layer/electron transmission 3 for a(1) knowing pole/layer/hole 偻 W W cathode, (2) anode/hole injection first layer/electron transport layer/layer transmission Layer/Light Emitting Layer/Ray v The compound of the present invention is formed by injecting a bile electron ...μ ... material and using (d) an electron injecting layer, or an organic a element by combining the organic $, , and miscellaneous materials usable in the present invention. Color 'red or white glow. The impurity is: high score; = machine f, luminescent material of the component or luminescent fluorescent whitening agent, laser pigment, daylight fluorescent material, "scintillator", various firefly 84 201226394 40550pifl The first __ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ The dopant material, the luminescent material of the triplet material described in P170 to 172, and the like. The compound which can be used as a light-emitting material or a light-emitting dopant is a polycyclic aromatic compound, a heterocyclic aromatic compound, an organic metal complex, a dye, a polymer light-emitting material, a styrene-based derivative, and an aromatic compound. An amine derivative, a coumarin derivative, a general derivative, a material touch, a conjugated compound having a spiro ring, a D contig, a derivative, and the like. Examples of polycyclic aromatic compounds ^ En 44 biological, phenanthrene derivatives ' thick tetraphenyl derivatives, flower derivatives, thick naphthalene derivatives, flower derivatives, succinic derivatives, red fired derivatives and the like. Examples of the heterogeneous aromatic compound are: an oxadiazole derivative having a dialkylamino group or a diarylamine group, a pyrazoloquinoline derivative, a pyridine derivative, a pyran derivative, a phenanthroline derivative, A fluorene heterocyclic derivative, a porphin derivative having a tris-amino group, and an anthracene. Bite _ derivatives and so on. Examples of organometallic complexes are: zinc, Ming, 铍, 铕, money, pin, silver, abundance, iron, gold, and other derivatives, benzopyrene derivatives. A complex of a diterpene derivative, a succinyl derivative, a stupid derivative, a transgene, a bite derivative, a morphine derivative, or the like. Examples of the pigments may be exemplified by: xanthene derivatives, polymethine derivatives, exoline f organisms, auxin derivatives, dicyanopyrene derivatives, diazomethylene methylene derivatives. a pigment such as a side oxy accompaniment, a scorpion venom derivative, a brain bacterium, a benzoxanthene derivative, a benzopyrene derivative, or a benzo-salt derivative. Examples of the polymer-based luminescent material are: a poly-p-styrene derivative, a polyphenanthene derivative, a poly-t-butyl-based deca-negative derivative, and a polylithic eve 85 201226394 40550 pifl. Revision date: March 1, 101, number 100140164 The Chinese manual does not have a sizing correction of a perylene derivative, a polyfluorene derivative, a polyparaphenylene derivative or the like. Examples of the stupid ethylene derivative are: an amine-containing styryl derivative, a styrene-based aryl derivative, and the like. Soil / Other electron transporting materials used in the organic EL device of the present invention can be used in a compound which can be used as an electron transporting compound in a photoconductive material towel, a compound which can be used in an organic EL element (IV) sub-transport layer and an electron-injecting layer. Choose to use. Specific examples of such an electron transporting material are: a thiophene-based metal complex, a 2, 2, ♦ specific bite derivative, a morphine derivative, a biphenyl derivative, an anthracene derivative, a "cephene derivative, Sanxiang Bio&quot;Secondary compound, metal complex of base derivative, decoy, compound, compound, gallium complex, benzophenone derivative, t sit and n; ;t丁生物&quot;Bixis do about the hair _« 枝物, etc. These specific examples are: ten-seat derivatives, use, biology, etc. One-side amines, phthalocyanine derivatives, materials; Formed by spin coating. The film method of each layer formed as a result of the properties of the binding material (4) Yinu, (4) limited 'can be rooted: hanging from 2 nm to 5000 nm range 86 201226394 4U55Upifl revised period: 101 years 3 In the Chinese manual No. 100140164 on the 1st of the month, there is no slash correction. In addition, the method of thinning the luminescent material is preferably a vapor deposition method because the impurities are homogeneous and the pores are formed by pinholes (pinhQies). 2. In the case of thinning using the vapor deposition method, the steaming conditions are based on the present The surface of the luminescent material of the bright material is the same. The steaming material is preferably set within the following range: the temperature of the heating boat is 5 〇 t 〜 4 〇〇 〇〇 为 10 10 10 10 10 10 10 Pa, evaporation rate The temperature of the substrate is -15 (TC ~ +300. It is better to support the board. Newly, as long as it has money _ degree, thermal stability and transparency = can be used, glass, transparent plastic film, etc.. The anode material can be used with metals, alloys, and guides with a power μ greater than 4 eV. =) T: AU and other metals, Cul, indium tin oxide % is ITO), Sn02, ZnO, etc. = (4) Metals with a rhyme less than 4 eV can be used 2 = gold and its specific example m 2 / clock, town / silver, _ Etc.: For: Ming/Fluorine, the transmittance of the electrode is (10) or more. The sheet resistance of the 2-pole is preferably several hundred Ω/□ to 5, the nature of the polar material, but usually at 10 nm~卜: Thickness = 1 〇nm~400 nm λα々々m 1 is preferably an electrode material, _ is set by ^. Such an electrode can be fabricated by using the luminescent material of the present invention using 5 of the above-mentioned members.Method-example, for the inclusion of the above-mentioned solar scale capable layer/hole transmission 87 201226394 4U33upiri No. 100140164 Chinese specification without slash correction This revision date:] 0 丨 March special delivery material, cathode organic EL element The film is formed by an anode method to form an anode tree: a film of a transmission layer, a thin electron transport material on which a light-emitting layer is formed, a thin film is formed, and a tantalum is formed by vapor deposition to form a cathode. A cathode was produced using the film of (4), whereby the target organic EL element was obtained. In addition, /f: = pass = in production can also reverse the production order, and the S = transport layer, the light-emitting layer, the hole transport layer, and the hole injection: in order. Under the θ anode, the voltage of the anode is used as the polarity of the anode and the cathode is the same as the anode. The voltage is about 2V~40V. == The electrode side (anode or cathode, and both sides) is observed. To the first month of the month = transparent: ^ machine EL device also emits light when the AC voltage is applied. This = the waveform of the AC power can be arbitrary. [Examples] Hereinafter, the present invention will be described in more detail based on examples. A synthesis example of the first compound used is explained below.合成 [Synthesis Example 1] Synthesis of compound (1-7-74) &lt;Synthesis of 9-(4-t-butylphenyl)anthracene&gt; Under a nitrogen atmosphere, 9 g of 9-bromoindole was added. 4_^acid 25 g, Qin Ph3)4 1&lt;3 g, potassium phosphate 51 g and the flask of "^ this 150 m! was given at reflux temperature for 21 hours. The reaction solution ς 88 201226394 is the Chinese manual No. 100M0164 No slash correction This correction date: March, 101! After the room temperature, 'add water and toluene for liquid separation sq), the solid precipitated by vacuum distillation to remove the solvent, using methanol After washing, it was washed with ethyl acetate to obtain 9-(4) tert-butylphenyl) hydrazine 28 g. &amp;&lt;9-bromo·1〇-(4-t-butylphenyl)fluorene synthesis&gt Adding N-bromosuccinimide to a flask to which 9-(4-t-butylphenyl)phosphonium 27 g, moth ι g and TtIF 3〇〇ml were added under nitrogen atmosphere 9 g was stirred at the bottom for 18 hours, and an aqueous solution of sodium thiosulfate was added to terminate the reaction. The solution was transferred to a liquid separation funnel and extracted by gas imitation. The body precipitated by distilling off the solvent under reduced pressure was collected by suction filtration, followed by recrystallization from chlorobenzene to obtain 9 g of bromine_10_(4_---t-phenyl) hydrazine. Synthesis of butyl &lt;3-(6-bromonaphthalen-2-yl)pyridine&gt; A flask containing 3 〇 咬 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 - Add 2 M of isopropyl chloride, / / solution of 35 ml. After the completion of the dropwise addition, the temperature is temporarily raised to room temperature, and the second material is cooled, and the edge is added, and zinc (di)diamine is added to the mixture. Then, after the temperature is lowered downstream of the room temperature, the addition of the trifluoromethyl is continued. Mix 18§ and 2 (dqing)^, at the reflux temperature, after H is cooled down to room temperature, in order to remove the gold of the catalyst, the addition of ions will be 3 times the molar relative to the target compound. The amine is dissolved in an appropriate amount of acid tetrasodium salt dihydrate (called EDTA.4Na aqueous solution) and toluene. After the solvent is removed by vacuum distillation, the column chromatography is carried out by gel column chromatography. 89 201226394 40550pifl Purification of the first capsular No. __ petal correction 1Q1 (four) benzene / acetic acid ethyl acetate = 7 / 3 (volume ratio)), to obtain 12 g of pyridine.夫不&lt;Synthesis of Compound (1-7-74)&gt; Adding Force - There are 3 (6H; 2_yl) σ (tetra) 6 2 g acid vinegar 5.9 g, bis(dipyridinium acetonide) (8) 〇4 g, tricyclohexyl squamous 5 g, acetamidine potassium 3.9 methoxyethyl bromide 5Qml flask under nitrogen atmosphere, mix under reflux. 9n was added to the solution towel. ♦ Tert-butylphenyl) 8.6 g, potassium phosphate 9 3 g, and ... trimethylbenzene % 2 was distilled off under normal temperature using Di Di 4 Dak. Add 5 ml of third butanol, 5 ml of water, bis (di-subunit, propylene, 0.4 g, and dicyclohexylphosphine G5g, further weighed at reflux temperature for 1 hour, and 1 reaction solution was cooled to room temperature. After washing with water and dissolving the salt, the solid is collected by suction; the lysate is obtained by washing with methanol, and then washed with acetic acid acetate, by driving column chromatography (acetic acid ethyl acetate = 9/1 (volume ratio)) Purification of the compound 'obtained compound (丨·^4): lead (four) ^ third butyl) phenyl) onion-9-based) Cai _2 boat than bite 〇 g. The structure of the compound was confirmed by nmr measurement. H-NMR (CDC13) . 5 = 9.07 (m, lH), 8.68 (dd, lH), 8·23 (m, 1H), 815 (ΜΗ), 8.08, 8.03 (m, 2H), 7.83 (dd, lH), 7.78 (d, 2H), 7.72 (d, 2H), 7 68 (dd, 1H), 7.63 (d, 2H), 7.42-7.48 (m, 3H), 7 3〇_7 38 (m, 4H), 149 (s, 9H) 〇 [Synthesis Example 2] Synthesis of Compound (1-7_26) &lt; Synthesis of 9-(3-indolylphenyl) fluorene > 90 201226394 40550pifl is the first screen Chinese manual _ line Fix this earn _ March 1 in the nitrogen roots 'will add 9 _ onion 36 g, 3 _ methyl stupid rotten acid 21 §, 卩 ?? 113) 41.4 §, potassium silicate 598 and 1,2,4_trimethylbenzene 15 〇 ml flask at the temperature of the shouting, 时. After cooling the anti-ship to room temperature, add water and toluene for liquid separation. After purifying the obtained toluene solution by using a short stone kiln column, the solvent was removed by distillation. To the obtained oil: heptane was added, and the precipitated solid was collected by suction filtration to obtain 9-(3-tolyl) oxime 31 g. Synthesis of 〇&lt;9-bromo-1〇-indolyl) oxime&gt; In a flask to which 9-(3-methylphenyl) 蒽3〇g and THF 2〇〇(5) were added, 'in a nitrogen atmosphere in ice Cool in the bath, add Ng Mobo Imine 20 g and iodine 0.1 g. After stirring at room temperature for 15 hours, an aqueous solution of sodium thiosulfate was added to stop the reaction. The solution was transferred to a liquid separation funnel, extracted with toluene, and purified using a short stone column. The solvent was removed by depressurization. To the obtained solution, heptane was added, and the precipitated solid was collected by suction filtration to obtain 9-bromo-l-(3-indolephenyl)indole. &lt;4,4,5,5-Tetramethyl-2-(10-(3-methylphenyl)phosphonium-9-yl)132 Synthesis of Dioxo-U-boron-pentane Ring&gt; 9-Bromo-10 will be added -(3-indolephenyl)蒽3〇g, 26 g of bis(dibenzylideneacetate)palladium (plutonium) 15 g, tricyclohexylphosphine i 4 g, potassium acetate 15 g, potassium carbonate 12 The flask of g and cyclopentyl decyl ether 1 〇〇 (6) was stirred under a nitrogen atmosphere at reflux temperature for 16 hours. After the reaction solution was cooled to room temperature, water and hydrazine were added for liquid separation, and the obtained benzene solution was purified by a short-twist hose column. The solvent was distilled off under reduced pressure, and heptane was added to the obtained oil, and the precipitated solid was collected by suction filtration to obtain 4, 4, 5, 5 - 91 201226394 U positive period: 1 March 1st, 1st oxygen [Synthesis of the pentyl ring 24 is the Chinese specification of the No. 100140164 without a slash correction of the quaternary methyl phenyl group), and the synthesis of &lt;&lt;&lt;&gt; The compound word is added with 4,4,5,5_four f-base_2_(1〇_(3_methylphenylidene)-1,3,2-dioxapentanyl 12 g, 3_(6_萘 _2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 After the solution was cooled to room temperature, water and toluene were added to carry out liquid separation, and the solvent was distilled off under reduced pressure. Purification by hydrazine column chromatography (methylene chloride / ethyl acetate = 20/1 (volume ratio)) After the crude product, it was recrystallized from a mixed solution of methyl bromide/heptane to obtain a compound (H26): tolyl)azinyl)naphthalene-2-yl)π-pyridyl 7"g. The structure of the compound was confirmed by NMR measurement. H-NMR (CDC13): 6 = 9.06 (m,lH), 8.67 (dd,lH) 8.22 ( m,lH) , 8.14 ( d,lH) , 8.06 ( m,lH) , 8.02 ( m,2H) 7.81 (m,lH) , 7.75 (d,2H) , 7.72 (d,2H) , 7.66 (dd,lH) ! 7.50 (t,1H ), 7.45( m,lH) , 7.27-7.39 ( m,7H) , 2.50 ( s, 3H) ° [Synthesis Example 3] Synthesis of compound (1-7-98) &lt;Synthesis of 9-(3-t-butylphenyl)anthracene&gt; - Deduction of 23 g, 2-(3-t-butylphenyl)·4,4,5,5-tetradecyl-1,3,2-dioxa pentyl 25 g, A flask of 3.1 g, potassium acetate 37 g, 1,2,4-dimercapto 250 m tert-butanol 5 〇mi and water 30 ml was stirred at reflux temperature for 21 hours. After the reaction solution was cooled to room temperature, water and a solution were added to carry out liquid separation. Use short rubber hose 92 201226394 40550pifl No Chinese painting for the 100140164 Chinese manual! I-line correction This correction date: 1 〇 1 year, March 1 column purification of the hydrazine solution, the solvent was distilled off under reduced pressure, and the solid precipitated by adding methanol was collected by suction to obtain 9-(3- Third butyl phenyl) 蒽 24 g. &lt;Synthesis of 9-bromo-10-(3-t-butylphenyl)anthracene> Addition of 9-(3-t-butylphenyl)anthracene 23 g, iodonium·ΐ g and THF 100 In a ml flask, 13 g of N-bromosuccinimide was added under a nitrogen atmosphere. After stirring at room temperature for 1 hour, an aqueous solution of sodium thiosulfate was added to stop the reaction. The solution was transferred to a liquid separation funnel for extraction with toluene. The obtained toluene solution was purified by a short-twist hose column, and after removing the solvent under reduced pressure, the residue was subjected to benzene/methanol reprecipitation to obtain 23 g of 9-bromo-10-(3-tert-butylphenyl)fluorene. &lt;Synthesis of Compound (1-7-98)&gt; 6.2 g of 3-(6-bromonaphthalen-2-yl)pyridine, 5.9 g of pinacol borate, and bis(dibenzylideneacetone) were added. A flask containing 4 g, 3 g of tricyclohexylphosphine, 3.9 g of potassium acetate and 50 ml of dimethoxyethane was shaken at reflux temperature for 4 hours under a nitrogen atmosphere. To this solution was added 9-bromo-1-indole-(3_t-butylphenyl)phosphonium 8.6 g, potassium phosphate 9.3 g and 1,2,4-trimethylbenzene 50 ml' using Dean-Star In the tube, the dimethoxyethane is distilled off by heating at normal temperature. 3 m Butanol 5 m Bu water 5 m b bis(diphenylidene acetonide) palladium (〇) 0.4 g and tricyclohexylphosphine ruthenium 5 g were added, and further stirred at reflux temperature for 2 hours. The reaction solution was cooled to room temperature, washed with water to dissolve the salt, and then a solid was collected by suction filtration. The obtained solid was purified by a ruthenium column chromatography (benzene/ethyl acetate = 9/1 (volume ratio)), and then recrystallized from toluene to obtain a compound (1-7-98): 3-( 6-(10-(3-Tertibutylphenyl) 93 201226394 40550pifl is No. 100140164 Chinese manual without scribe correction. Amendment date: March 1, 101 蒽-9-yl)naphthalen-2-yl) ° is 1.5 g more than a bite. The structure of the compound was confirmed by NMR measurement. !H-NMR (CDC13) · 6 = 9.07 (m,lH) , 8.68 (dd,lH), 8.23 (s,lH) , 8.16 (d,lH) ,8.08 (m,lH) ,8.03 (m,2H) ), 7.83 (m, lH), 7.75 (d, 2H), 7.72 (d, 2H), 7.68 (m, lH), 7.52-7.61 (m, 3H), 7.46 (m, lH), 7.30-7.38 ( m, 5H), 1.41 (s, 9H). [Synthesis Example 4] Synthesis of Compound (1-7-96) <2-(10-(4-Tertiaryphenyl) Onion-9-yl)-4,4,5,5-tetradecyl- Synthesis of 1,3,2-dioxaborolane&gt; 9-bromo-10-(4-t-butylphenyl)phosphonium 7.8 g, benzoic acid pinacol ester 6.1 g, bis ( Dibenzylideneacetate) 妃(〇) 〇.3 g, tricyclohexylphosphine 〇.3 g, potassium acetate 3.9 g, potassium carbonate 2.8 g, and cyclopentyl decyl ether 40 ml flask under nitrogen atmosphere Stir at reflux temperature for 6 5 hours. After the reaction solution was cooled to room temperature, water and toluene were added to carry out liquid separation, and the solvent was removed under reduced pressure. Heptane is added to the obtained oil, and the precipitated solid is collected by suction filtration to obtain 2_(1〇((4_t-butylphenyl)phosphonium-9-yl)_4,4,5,5_4 Base-1,3,2-oxaxanthene 6.9 g. &lt;Synthesis of 4-(3-(6-bromonaphthalen-2-yl)phenylbipyridine)&gt; 4-(3-bromophenyl)pyridine 9.8 g and THF 2 〇 ml were added under a nitrogen atmosphere The flask was cooled to -70 ° C in a dry ice / methanol bath, and slowly added dropwise 2.6 正 of n-butyl lithium 17 m after the addition was completed, and the mixture was mixed at the same temperature for an hour, and zinc chloride tetramethyl b was added. Diamine complex 12 g. Thereafter, after stirring for 1.5 hours at I to warm, add 3 Duncan acid 6_ desert naphthalene_2_vinegar 15 94 201226394 40550pifl to the first 〇0〗4〇164 Chinese manual without slash correction This revision date: 丨0丨年1月1日g, 双(二亚录丙咖(8) and U·双(diphenylphosphino) propyl Hyun 0.5 g, at H degree _ !hour. After the reaction is completed, add A · :: water ethyl ester for liquid separation 'after distillation under reduced pressure to remove the dissolved tablets, 'tog' raw oxide column chromatography (toluene / acetic acid ethyl acetate = 9 / 1 (volume Purification was carried out by washing with methanol, followed by recrystallization from ethyl acetate/methanol mixed solvent t to obtain 4_(3_(6_ desert pyridine 5.3 g. J ❹ &lt; compound (1-7-96) ) Synthesis &gt; Ο will be added - (1〇_(4_Thirdyl) Phenyl) Hui_9-based) 4,4,55-tetramethyl-1,3,2-dioxaborolan 6"g, 4_(3_(tetra)naphthalene-2-yl)phenylpyridinium 5= a flask of g1, Pd〇&gt;Ph3)4 〇.5 g, potassium phosphate 3 〇g, 12,4 trimethylbenzene in ml, third butanol 5 ml and water 5 (f) was stirred at reflux temperature for 6 days. ^ After cooling the reaction solution to room temperature, add EDTA · aqueous solution and: benzene for liquid separation, and remove the solvent under reduced pressure. By active oxidation = column chromatography (A stupid / acetic acid ethyl g |: = 9 / 1 (volume ratio)) The crude product obtained was purified by distillation under reduced pressure using a solvent, and the solid was washed, and then recrystallized from toluene to obtain a compound (H%). (3-(6) : (10-(4_T-butylphenyl) piperidinyl)naphthalen-2-yl)phenyl)d is pyridine 3·3 g. The structure of the compound was confirmed by NMR measurement. h-NMR (CDC13) : 8.73 (dd, 2H), 8.27 (m, lH), 8.15 ^51Η), 8.03 Cm, 3H), 7.99 (m, 2H), 7.78 (d, 2H), 773 ^, 2H), 7.61^7.70 ( m, 7H), 7.44 (m, 2H), 7.30^738 (m, 4H), 1.49 (s, 9H). [Synthesis Example 5] Synthesis of Compound (1-14-14) 95 201226394 40550pifl Revision date: March 1, 1st, 1st, 100th, 140th, Chinese manual, no underline correction, &lt; 9_〇ethoxyphenyl )] Synthesis of 〇_(naphthalene-2-yl) onion> "Addition of 1-oxa-3-acetyl phenylbenzene 72 4 g, (1〇_(naphthalene-2-yl) onion) boric acid to the burnt 104.5 g, Pd(Pph3)4 1〇4 g, phosphoric acid _ 127 4 g, 1/, 4-dimethylbenzene 600 m b 2-diol 12 〇m b and water 12 〇 ml, under nitrogen = environment 'At the temperature of the phase flow _ M, hour. Cool the anti-ship to the chamber to absorb the suction, collect the solid of the liquid towel, wash it with Xiang, and obtain 9 points of ethoxyphenyl)-10-(naphthalene-2-based蒽82 g. &lt;Synthesis of 3-(10-(naphthalen-2-yl)-enyl)benz> and the addition of 9·(3'ethoxyphenyl)·1()-(naphthalene) ·2·基)蒽82 g $2, I salt 446.0 g' was searched under reflux in a nitrogen atmosphere. The reaction solution was cooled to room temperature, then water was added, and the solid was washed with methanol and reused. Washing with toluene, g 3-called naphthyl) 蒽-9-yl) cumbersome 76 〇g. Served &gt;&lt;trifluoromethane calcination acid MM naphthalene_2_yl) 蒽冬基) (76 °§) λώ二知田生Ί Cool in the valley, under the nitrogen atmosphere, drop 65.0 g of difluoromethane anhydride. Drop six-display% half-yield 6, 'mix for 15 hours, add water,】 / Canadian dollar After the completion of the step, the solid was washed in the warmth, and the money was collected and precipitated. The methanol was used as the ester of 90.3 g. The gas was burned with acid 3-(10-(na-2-yl).惹_9_基) &lt; 4,4,5,5-tetramethyl | ^ -2- ^ -9^ ) ^ Add trifluoromethyl acid to the flask (3 side naphthalene · 2 base) hopper base) 96 201226394 ^UDDUplfl Amendment date: March 1, 1st, No. 164 Chinese _ Difficulty = Amendment = 2 3 delete __52.ι§, double (two subunits L i and = hexyl phosphine 7.2§, acetic acid _ no 雍, ; ^, ! ^ ml, 5 hours at the reflux temperature, will be filtered to remove insoluble matter, using EDTA &amp; Tongshan leak · + 仃 仃 W, Γ 4Na aqueous solution Wash the solid obtained by the solvent of the nuclear steaming liquid, Ο G: male 曱 base_2_(3. (naphthalene) onion _9·yl) phenyl)-1,3,2 -monooxa-pentane (52.0 g). &lt;Synthesis of Compound (1-14-14)&gt; A) Addition of benzene to At 2 to 2,5,5-tetramethyl _2 〇 〇 - (naphthalene I base) 蒽 2 〇 L 乳 杂 戊 8.6 8.6 8.6 g, by this patent special. 5,-Bromo-3-indolyl-2,2,-bipyridin 5 Pd(m3) 40.6 g, potassium phosphate 7.2 g, trimethylbenzene 25 1 di-butanol 5 ml, synthesized by the method And water 1 m Bu disturbed 2 5 small ^ at the reflux temperature. After the counter-test was cooled to room temperature, water was added, and the solid of the bribe collecting liquid was washed with methanol. The solid was purified by column chromatography (toluene/f-ethyl acetate = 9/1 (volume ratio)), followed by active carbon column chromatography. The solution is concentrated and recrystallized from the gas material to obtain the compound (1_14-14)······················ 2, 2, · paired to 2·3 g. The structure of the wei compound was confirmed by NMR measurement. H-NMR (CDC13): δ = 9.〇5(ιη5ΐΗ), 8.55(d,lH), 8.11 (dd,lH), 8.09(d,lH), 8.02(m5iH), 8.00(S,1H), 7.73-7.95 (m,9H) , 7.60 (m,5H) , 7.30-7.40 (m,4H) , 7.23 (m,lH), 97 201226394 is the Chinese manual No. 100140164 without a slash correction. Amendment date: 1〇 2.56 (s, 3H) on March 1, 1st. [Synthesis Example 6] Synthesis of Compound (MM) &lt; Synthesis of 2-methyl-4_(6-(l〇-phenylfluoren-9-yl)naphthalen-2-yl)pyridine> 4, 4, 5 ,5-tetradecyl-2-(6-(10-phenylindole-9-yl)naphthalen-2-yl)-1,3,2-dioxaborolan (2.(^), 4 -Bromo-2-indolylpyridine (0.8§), Pd(PPh3)4 (0.3 g), potassium phosphate (ι·7 g), ι, 2,4-trimethylbenzene (20 ml), third Alcohol (5 ml) and water (丨 ml) were added to the flask, and stirred under a nitrogen atmosphere at reflux temperature for 7.5 hours. After the heating was completed, the reaction solution was cooled to room temperature, and water and benzene were added for liquid separation. The obtained solid was purified by pressure distillation to remove the "treat agent" by means of Shih Hose column chromatography (developing solvent: toluene / ethyl acetate = 95/5). Then, the obtained eluate was passed. Into the short activated carbon tube column, the coloring component is removed, the reduced pressure is collected, and the precipitated crystals are removed by distillation to obtain the compound represented by (mm) 2_methyl_4_(6_(1〇_stupid)蒽9_yl)naphthalen-2-yl)π-pyridinyl (0.7 g) The structure of the compound was confirmed by NMR measurement. 1H-NMR (CDCl3): 5 = 8.66 (d, lH) ), 8.30 (s, lH), 8.17 (d, lH), 8.03 (m, 2H), 7.87 (d, lH), 7.72-7.78 (m, 4H), 7.70 (d, lH), 7.65 (m, 2H), 7.58 (m, 2H), 7.56 (m, 3H), 7.31-7.39 (m, 4H), 2.73 (S, 3H). [Synthesis Example 7] Synthesis of Compound (1-11-2) &lt; Synthesis of 3 fluorenyl 4 (6-(i〇_phenylindole-9-yl)naphthalene-2-yl) as defined by > 4,W,5-tetramethyl-2·(6-(10-benzene)蒽 蒽 ) ) 萘 萘 萘 萘 萘 萘 萘 萘 萘 萘 萘 萘 萘 萘 萘 萘 萘 萘 萘 萘 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 98 March! No marking correction for the Chinese manual of IOOMOI64 (1.0 g), Pd(PPh3)4 (0.3 g), potassium phosphate (1.7 g), 1,2 4 dimethylbenzene (20 ml), third butanol (5 ml) and water (lml) Stir into &amp; bottle' under nitrogen for 24.5 hours at reflux temperature. After the addition, the reaction solution was cooled to room temperature, and water and toluene were added to carry out liquid separation. The solvent was evaporated under reduced pressure, and the obtained solid was purified by silica gel column chromatography (eluent: toluene / ethyl acetate = 95/5). Next, the selected eluate is passed through a short carbon to remove the coloring component. The crystal precipitated in the process of removing the obtained filtrate was further reduced by a weight of two, and further recrystallized in toluene to obtain a compound represented by (1-11 2), which is a 4-(6-(10-phenylfluoren-9-yl) group. Naphthalene-2-yl)pyridine (〇.5 g). The structure of the compound was confirmed by NMR measurement. H-NMR (CDC13): 6 = 8.62 (s,lH), 8.58 (d,lH) 8 13 (d,lH) , 8.06 (S,1H) , 8.02 (d,lH) , 7.99 (s,iH) 7 75 (d,4H),7·70 (dd,lH) , 7.65 (t,2H),7.59 (t,2H) '7 53 (m,2H) ,7.33-7.39 (m,5H) ,2.44 ( s, 3H)〇'. [Synthesis Example 8] Synthesis of Compound (1-11-3) &lt;2methyl 5-(6·(1〇_本基蒽_9_yl)naphthalene_2^)π ratio The synthesis of bite will be 4,4,5,5-tetramethyl_2_(6_(1〇•phenyl hydrazine) mouth Cai PdPp3^ (PPh3) 4 (0.15g), potassium phosphate (17g), u bucket Three, for example, third butanol C5ml, $丄-τ soil It gas 璜Μ - () water () was added to the flask, under the broth, stirring at the reflux temperature τ 5 . The solution is cooled to the palace, ®, and * l. The two additions of water and toluene are removed for liquid separation. Vacuum distillation ', 'J fines by 矽 rubber column chromatography (deployment liquid: A stupid / acetic acid B 99 201226394 40550pifl for the 100140164 Chinese manual no line correction) Amendment date: March 1, 1 = 95/5) Purification of the solid obtained. The solid obtained by distilling off the solvent under reduced pressure was recrystallized from toluene to obtain the compound represented by (M1-3) 2-mercapto-5-(6-(10-phenylfluoren-9-yl)naphthalene. -2- carbylpyridinium (1.2 g). The structure of the compound was confirmed by NMR measurement. ^-NMR (CDC13): δ = 8.95 (m, lH), 8.20 (s, lH), 8.14 (d, lH) ) , 8.01 ( m,2H) , 7.96 ( dd,lH) , 7.81 ( dd,lH) , 7.74 (m,4H) , 7.67 (dd,lH) , 7.63 (t,2H) , 7.57 (t,lH) 7.52 (m, 2H), 7.30-7.37 (m, 5H), 2.67 (s, 3H) [Synthesis Example 9] Synthesis of Compound (1-11-4) &lt;3-methyl-5-(6 Synthesis of -(10-acidyl-9-yl)naphthalen-2-yl)acridine &gt; 4,4,5,5-tetramethyl-2-(6-(10-phenylindole-9) -yl)naphthalen-2-yl)-1,3,2-dioxaborolane (2.0 g), 3-bromo-5-mercaptoacridine (0.8 g), hydrazine (1 (?? 113) 4 (0_3 §), potassium phosphate (1.7 §), 1,2,4-trimethylbenzene (2〇1111), third butanol (5 ml) and water (1 ml) were added to the flask under nitrogen Under the environment, stir at reflux temperature for 7.5 hours. After the heating is completed, the reaction solution is cooled to room temperature, and water and toluene are added for liquid separation. The solvent is distilled off under reduced pressure, and the solvent is removed by vacuum distillation. The obtained solid was purified by column chromatography (developing solution: toluene / ethyl acetate = 95/5). Then, the obtained eluate was passed through a short activated carbon tube column to remove the coloring component. The solvent was distilled off under reduced pressure. And heptane was added for reprecipitation to obtain the compound represented by (1-11-4) 3-mercapto-5-(6-(10-phenylfluoren-9-yl)naphthalen-2-yl)acridine ( 1.3 g) The structure of the compound was confirmed by NMR measurement. !H-NMR (CDCI3): 5 = 8.87 (m, lH), 8.51 (m, lH), 8.22 (s?lH), 8.15 (d, lH) ), 8.03 (m, 2H), 7.89 (m, lH), 100 201226394 40550pifl is the ΙΟΟΜΟΙΜ Chinese manual without a slash correction. ^ Date: March 1, 101 7.83 (dd, lH), 7.73 (m , 4H), 7.67 (ddlH, 7.57 (t, 1H), 7.52 (m, 2H), 7 3G_7 37 (^, 7.63 (m, 2H), [Synthesis Example 10] Synthesis of compound (1_U_5), 2.49 ( s, 3h). &lt;4,Methyl-3·(6·(1··笨笨9_基)丄 Synthesis of 4,4,5,5_tetramethyl·2_(6_(1〇_Benzene)) 〉 ^)-U (2&gt;〇g).3-^:4^^)#·2· (1.0 g), Pd(PPh3)4 (0.3 g), potassium phosphate pyridine hydrochloride hydrazine benzene ( 20 ml), tributanol (5 ml) and water 1, 1,2,4-trimium, under a nitrogen atmosphere, stirring at reflux temperature 7^1), after adding to the flask, the reaction solution was cooled to room temperature. The obtained solid was purified by adding water and toluene = a reduced-pressure distillation _, by means of chromatography; benzene (10) vinegar = 95/5). Next, the two-two's liquid is passed through a short carbon residue to remove the coloring component. The solvent was removed by distillation under reduced pressure. The obtained solid was recrystallized from toluene to give the compound represented by (^^5) 4-methyl-3-(6-(10-phenylfluoren-9-yl) ) naphthalen-2-yl) 吼 口 定 (0.6 g). The structure of the compound was confirmed by NMR measurement. 'H-NMR(CDC13) : δ = 8.64 ( s,lH) , 8.55 ( d,lH) , 8.14 (d,lH) , 8.06 (S,1H) , 8.02 (d,lH) , 7.99 (s,lH ), 7.76 (m, 4H), 7.70 (dd, lH), 7.63 (m, 2H), 7.59 (t, 2H), 7.53 (m, 2H), 7.32 - 7.39 (m, 4H), 7.30 (d, lH), 2.45 (s, 3H). [Synthesis Example U] Synthesis of Compound (MI-6) &lt;Synthesis of 2-indolyl-3-(6-(i〇-phenylindolinyl)naphthalene-2-yl)acridine> 4, 4 ,5,5·tetramethyl-2·(6·(10-phenylindolinyl)naphthalene-2-101 201226394 40550pifl is the Chinese manual of No. 100140164 without a slash correction. Amendment date: March 1st, 1st 1-day)-1,3,2-dioxaborolan (2.0 g), 3-bromo-2-indenyl acridine (0.8 g), ?(1(?卩113)4(0.15§) Potassium phosphate (1.7§), 1,2,4-trimethylbenzene (20 ml), third butanol (5 ml) and water (1 ml) were added to the flask under nitrogen at reflux temperature After stirring for 4 hours, after the completion of the heating, the reaction solution was cooled to room temperature, and water and toluene were added for liquid separation. The solvent was distilled off under reduced pressure, and the mixture was purified by column chromatography (eluent: toluene/ethyl acetate = 95) /5) Purification of the obtained solid. Then, the obtained eluate was passed through a short activated carbon tube column to remove the coloring component. The solvent was distilled off under reduced pressure, and heptane was added for reprecipitation to obtain (1-11-6). The compound represented is 2-mercapto-3-(6-(10-phenylidino-9-yl)naphthalen-2-ylbipyridinium (1.1 g). The structure of the compound was confirmed by NMR. ^-NMRCCDC^): 5 = 8.60 (m, lH), 8.11 (d, lH), 8.05 (s, lH), 8.00 (d, lH), 7.96 (s, lH) ), 7.74 (m, 4H), 7.69 (m, 2H), 7.63 (m, 2H), 7.57 (m, 2H), 7.52 (m, 2H), 7.30-7.37 (m, 4H), 7.28 (m, lH), 2.66 (s, 3H) [Synthesis Example 12] Synthesis of Compound (1-11-8) &lt; 5-Mercapto-2-(6-(10-phenylfluoren-9-yl)naphthalene- Synthesis of 2-base) acridine &gt; 4,4,5,5-tetradecyl-2-(6-(10-phenylfluoren-9-yl)naphthalen-2-yl)-1,3, 2-dioxaborolan (2.5 g), 3-bromo-2-indenyl acridine (1.0 g), Pd(PPh3)4 (0.15 g), potassium phosphate (2.1 g), 1,2,4 - Trimethylbenzene (20 ml), tert-butanol (5 ml) and water (1 ml) were added to the flask, and stirred under reflux for 18 hours under a nitrogen atmosphere. After the heating was completed, the reaction solution was cooled. The precipitated solid was collected by suction filtration at room temperature. The obtained solid was purified by ruthenium column chromatography (developing solution: toluene). Next, 102 201226394 40550 pifl was modified: 〇1年1月1 The Japanese manual No. 100140164 has no scribe line correction. The obtained solution is passed into a short activated carbon tube column. Removing coloring components. The solvent was removed by distillation under reduced pressure. Ethyl acetate was added to re-salt to obtain the compound 5-(indolyl-2-(6-(10-phenyl)naphthalen-2-yl) σ-pyridinidine (uu). 1.5 g) The structure of the compound was confirmed by NMR measurement. ^-NMRCCDCls): 6 = 8.63 (m, 2H), 8.23 (dd, lH), 8.16 U, 1H), 8.00 (m, 2H), 7.86 (d, lH), 7.73 (m, 4H), 〇 7-6〇-7.67 (m, 4H), 7.56 (t?lH), 7.51 (m, 2H), 7.30-7.36 (m, 4H), 2.44 (s, 3H) ° [Synthesis Example 13] Compound (1) Synthesis of -11-39) &lt;Synthesis of 5-bromo-2'-methyl-3,4,-bipyridyl> Addition of 4_ _2 曱 曱 喊 (13 8g) and toluene (i5〇) Mi) Ding = cooling in (4) / dry ice bath. To this solution, a positively burned solution of i6M (55 ml) was added dropwise. After the completion of the dropwise addition, add acetone zinc tetramethylethylenediamine to THF (45 (4) in acetone/dry (2 3 '-side while mixing 1 / J, while removing the acetone/dry ice bath and heat up. In the ^ ^ ^ force mouth, toluene (2 〇 ml), 3, 5 · two desert (19 hearts) liquid cooled to m reflow temperature for 2 hours. The reaction is under reduced pressure; ί, scale to cut liquid and Toluene is used for liquid separation. The toluene/ethyl ship '(4) Nalu riding method (expanding liquid: learning experiment into ρί) is used to purify the obtained solid. At this time, refer to the "organic r treatment method and separation and purification method -" chemical same liquid The rate of 醆2 in the second page is two pages: the method 'slowly increases the expansion of the four 曰 ,, so that the target dissolves. Then, reduce the steaming 103 201226394 40550pifl Revision date: March 1, 101 No. 100_64 Chinese Standard Specification No solvent correction, the solvent was removed, and the obtained solid was recrystallized from heptane to obtain hydrazine bromide-2'-mercapto-3,4'-linked. The ratio σ is determined (5.3 g). Synthesis of 2'-mercapto-5-(6-(1〇-phenylindole-9-yl)naphthalene-2-yl)_3,4,-bipyridyl&gt; 4,4,5,5- Tetramethyl 2_(6_(1〇_phenylindole_9_yl)naphthalene_2 _ base)-1,3,2-dioxaborolan (2.5 g), 5-di-2,-methyl-3,4'-linked n-pyridinium (1.1 g), Pd(PPh3)4 (〇·ΐ5 g), filling and unloading (ι·7 g), 1,2,4-three Base benzene (20 ml), third butanol (5 ml) and water (丨1) were added to the flask, and stirred at reflux temperature for 3 hours under a nitrogen atmosphere. After the heating was completed, 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 = 1/1). The solvent was distilled off under reduced pressure, and the obtained solid was recrystallized from toluene to obtain the compound 2'-mercapto-5-(6-(10-phenylfluoren-9-yl)naphthalene represented by (1-11-39). 2-yl)-3,4'-bipyridyl (0.3 g). The structure of the compound was confirmed by NMR measurement. ^-NMRCCDCls): 5 = 9.11 (m, lH), 8.92 (m, lH), 8.65 (d, lH), 8.28 (m, 2H), 8.17 (d, lH), 8.05 (m, 2H), 7.87 (d,lH), 7.68-7.75 (m,5H), 7.61 (m,2H), 7.56 (t,lH), 7.51(m,3H), 7.45(m,lH),7.30-7.37(m,4H ), 2.70 (s, 3H). [Synthesis Example 14] Synthesis of Compound (1-14-2) &lt; Synthesis of 3-mercapto-4-(3-(10-(naphthalen-2-yl)fluorene-9-yl)phenyl Ratio π &gt; Add 4,4,5,5-tetradecyl-2-(3-(10-(naphthalen-2-yl)fluoren-9-yl)benzene 104 201226394 • One γ 丄 '丄 Revision date: 1〇 1 year March 1 is the 10G14G164 Chinese manual _ line correction of the penta ring (2.5 g), 4, α3,). d (pPh3) 4 (0,5 ί tl 5 diol 5 ml, and water 1 ml, The mixture was stirred at reflux temperature for 11.5 hours. The reaction solution was cooled to room temperature to see liquid separation. Decompression tombstone removal, .^^丨'], plus Jiaben and water into the oxime: diacetate B (IV) 5/5) Purify the obtained solid. Then, the liquid is passed through a short carbon to remove the coloring component. Reduce the ❹, the mine to the axis, add the Qiqiuqiu, Lin (1_14_2) = the compound 3•methyl donor (naphthalene) _2___9•yl) pyridine (1·4 g) The structure of the compound was confirmed by NMR measurement. H-NMR (CDC13): δ= 8.53 ( s, 1 Η) , 8.50 ( d,lH ) , 8.08 (dd, lH), 8.02( m,lH), 7.97( d,lH), 7.92(7.70-7.78 (m,5H) , 7.48-7.63 (m,6H) , 7.35-7.39 (m,2H) , 7.29-7 34 (m, 3H), 2.41 (S, 3H). Example 15] Synthesis of Compound (1-14-3) &lt; Synthesis of 2-mercapto-5-(3-(10-(naphthalen-2-yl)fluoren-9-yl)phenyl)acridine Add M,5,5-tetradecyl_2_(3_(10_(naphthalenyl)蒽9yl)phenyl)-1,3,2-dioxaborolan (2 5 g), 5_Mo _2_mercaptopyridine (丄〇旦), Pd(PPh3)4 (〇·35 g ), phosphate unloading (3·2 g ), 1,2,4-trimethylbenzene 2〇m b second Alcohol 5 ηύ, and water 1 mi, stirred at reflux temperature for 8 5 hours. After cooling the reaction solution to room temperature, the precipitated solid was collected by suction filtration. /ethyl acetate=95/5) Purification plant 105 201226394 40550pifl Revision date: 1 year of March is the first Chinese manual of lOOHOl64 without painting! (Line correction of the solid obtained. Then 'pass the obtained dissolution solution The coloring component was removed by a short-acting hydrazine column, and the solvent was distilled off under reduced pressure, and the obtained solid was washed with ethyl acetate to obtain the compound i-(5-14) represented by (1-14-3) -5-(3-(10) - (Qin-2-yl) onion-9-yl)phenyl) bite (1.5 g). The structure of the compound was confirmed by NMR measurement. ^-NMRCCDCla): 5 = 8.45 (m, lH), 8.08 (d, lH), 8 〇 3 (m, lH), 7.99 (s, lH), 7.93 (m5lH), 7.87 (dd, lH), 7.7 〇V8l (m,7H), 7.57-7.63( m,3H), 7.54( m,lH), 7.30-7.40( m 4Hλ 7.23 (d,lH) ,2.61 (s,3H)° ' ' [Synthesis Example 16 Synthesis of Compound (1-14-11) &lt;Synthesis of 5-indol-6'-mercapto-2,2'-linked hydrazine&gt; A flask to which 2-bromo-6-mercaptopyridine (5.2 g) and cyclopentyl decyl ether (3 ml) were added was cooled in a methanol/dry ice bath. To the solution was added dropwise a 16% solution of n-butyl chain in hexane (22 ml). After the completion of the dropwise addition, the mixture was stirred for 2 hours while cooling in an alcohol/dry ice bath, and zinc chloride tetradecylethylenediamine (8.3 g) was added to remove methanol/dry ice and heat. After warming to room temperature, 2,5-dibromopyridine (u g) and pd(pph3)4 (1 〇 g) were added, and the temperature was 3.5 hours. After the reaction solution was cooled to room temperature, a coffee aqueous solution of AI/Na and benzene were added to carry out liquid separation. After decomposing under reduced pressure, the solution was followed by 'Solid solution: solid obtained by toluene/ethyl acetate. At this time, the ethyl acetate white ratio in the developing solution was slowly increased'. The target was dissolved. Then, the solvent was removed by evaporation under reduced pressure, and the obtained solid was recrystallized from heptane to obtain 5-bromo-6, _^pyridine (1.4 g)., butyl soil, _ ear 106 201226394 40550pifl is the Chinese manual of the 100th H0164 without a slash correction. The date of this revision: March 1, 101 &lt; 6'-nonylnaphthalene_2_yl) cockroach base) stupid base _2 2,_bipyridine synthesis &gt Add 4,4,5,5-tetradecyl-2-(3-(10-(naphthalen-2-yl)fluoren-9-yl)phenyl)_1'3,2-mono-female ring (2.0 g), 5_ desert-6'-mercapto-2, 2'-linked π ratio π (l.〇g), Pd(PPh3)4 (〇_15g), potassium phosphate (1.7g), 1,2,4-trimethylbenzene 20 ml, third butanol 5 ml, and water 1 m were mixed at reflux temperature for 7.5 hours. After the reaction solution was cooled to room temperature, a solid which precipitated ruthenium was collected by suction filtration. The obtained solid was purified by ruthenium column chromatography (developing solution: toluene / ethyl acetate == 95/5), and the obtained eluate was directly subjected to suction filtration using a Kiriyama funnel coated with activated carbon. Coloring ingredients. The solvent was distilled off under reduced pressure. Ethyl acetate was added and reprecipitated to obtain the compound 6 represented by (1 to 14-11), -mercapto-5-(3-(10-(naphthalen-2-yl)fluorene-9-yl) Phenyl)-2,2'-bipyridyl (1.2 g). The structure of the compound was confirmed by NMR measurement. ^-NMR (CDC13) : 6 = 9.03 (m,lH) , 8.49 (dd,lH) 8-22 (d,lH) , 8.09 (m,2H) , 8.03 (m,lH) , 8.00 (s,lH ), 7.93 (m, lH), 7.87 (d, lH), 7.68-7.83 (m, 7H), 7.55-7.64 (m, 4H), 7.30-7.40 (m, 4H), 7.17 (d, lH), 2.65 (s, 3H) 〇 [Synthesis Example 17] Synthesis of Compound (1-14-12) &lt;5-&gt; Synthesis of odor-5'-methyl-2,2'-linked η ratio bite> Toluene with 2-bromo-5-mercaptopyridine (1.7 g) and THF (5 ml) was added dropwise to the solution under ice bath_cooling. 2]V [isopropyl chlorinated THF solution ( 5.5 ml). After the completion of the dropwise addition, remove the ice bath and stir at room temperature for 3·5 hours, then cool again in the ice bath, add zinc hydride tetrakilium bromide 107 201226394 40550pifl to the 100140164 Chinese manual without a slash correction. The flood season is called March! Diamine (2.8 g). After removing the ice bath and warming to room temperature, 2,y two bites (2.4 g) and Pd(PPh3)4 (〇.35 g) were added and given at reflux temperature for 'hours. After cooling the reaction solution to room temperature, EDTA· and toluene were added for liquid separation. After the solvent was distilled off under reduced pressure, the solid of ?? was purified by column chromatography (eluent: benzene/ethyl acetate). The solvent was distilled off under reduced pressure, and heptane was added to reprecipitate, 5-di-5'-mercapto-2,2'-linked. Than bite (1.5 g). &lt;5-Methyl-5'·(3-(1〇-(naphthalen-2-yl)indole_9_yl)phenyl)_2,2·_ Synthesis of bipyridyl&gt;&amp; Add 4,4, 5,5·tetradecyl-2-(3-(10-(naphthalen-2-yl)fluoren-9-yl)phenyl)-1,3,2-dioxaborolan (2.0 g), 5-Moly-5'-mercapto-2,2,- out-of-bit bite (1.2§), 卩(1yang113)4(〇.15§), potassium phosphate (1.7§), 1,2,4 - 20 ml of trimethylbenzene, 5 ml of third butanol, and 1 ml of water were mixed for 6 hours at reflux temperature. After the reaction solution was cooled to room temperature, toluene and water were added to carry out liquid separation. The solvent was distilled off under reduced pressure, and the obtained solid was purified by silica gel column chromatography (eluent: benzene/ethyl acetate = 95/5), and the obtained solvent was passed through a short activated carbon column to remove Coloring ingredients. The solvent was removed under reduced pressure to remove the solvent, and ethyl acetate was added to reprecipitate, and the obtained solid was further recrystallized from toluene to obtain the compound represented by (1_14_12) 5 - fluorenyl-5'-(3_( 1〇-(naphthyl)蒽!yl)phenyl)_2,2,_biacidine (i 2 g). The structure of the compound was confirmed by NMR measurement. 'H-NMRC CDC13) : δ = 9.03 (ΙΪΙ,ΙΗ) , 8.52 ( s,lH) , 8.44 (dd,lH) , 8.33 (d,lH) , 8.09 (m,lH) , 8.03 (m,lH) , 8.〇〇108 201226394, • Λ Λ. JL • WV/1 Revision date: March 101 is the 100M0164 Chinese manual without line correction (s, 2H), 7.93 (m, lH), 7.87 ( m, lH), 7.73-7.83 (m, 6H), 7.56-7.66 (m, 5H), 7.31-7.39 (m, 4H) 2 41 (s 3H). [Synthesis Example 18] Synthesis of Compound (1_14_13) &lt; 5 -&gt; Synthesis of odor-4-mercapto-2,2'-linked oxime 定 o Addition - shoulder ice methyl group such as 9 g And the thf (9) ring flask was cooled in an ice bath. To this solution was added dropwise 2 M isopropyl chloride = THF solution (24 mi). After the completion of the dropwise addition, the ice bath was removed and observed at room temperature for 2 hours, and then cooled again in an ice bath, and zinc chloride tetramethylethylene "amine 12.1 g" was added. After removing the ice bath and warming to room temperature, 'addition two Fill in 9:5 g) and Pd(PPh3)4 (l 4g), and remove it at reflux temperature. After cooling the reaction solution to room temperature, add EDTA · 4Na aqueous solution to separate. After distilling off the solvent under reduced pressure, borrow Add 4,4,5,5-tetramethyl 1 (3) from the base of Shishijiao o, 5'·(3, (naphthalene-2-based) phenyl)·2,2,♦ Supply (naphthalene-2-yl) lean _9 (2'°s)' base benzene (four) hours. The reaction: cold two chamber separation. The solvent was distilled off under reduced pressure: liquid: benzene/acetic acid B (four) coffee heart = :109 201226394 40550pifl Revision date: January 1, 1st is the 10014014 Chinese manual. The eluate without the sizing correction is passed through a short activated carbon tube column to remove the coloring component. The solvent is distilled off under reduced pressure. The alkane was washed, whereby the servant (1.4 g) which was interposed (144-13) was obtained. The structure of the compound was confirmed by NMR measurement. ^-NMRCCDCls): 5 = 9.04 (m, lH), 8.55 (d, lH), 8.47 (dd, lH), 8.28 ( s, lH) , 8 .11 ( dd,lH) , 8.09 ( d,lH) , 8 03 (m,lH), 8.00(s,lH), 7.93(m,lH), 7.88(d,lH), 7.73.7 83 (m ,6H), 7.57-7.63( m,4H),7,30-7.40(m,4H),714( djH) 2.45 (s,3H) ° ' ' 'L synthesis of sputum, ▲ m , and the synthesis of 5-5-6-mercapto-2,3'-linked η ratio bite will be added with 5-week-2-methyl bite (3 4 g) and (1〇〇) The flask was cooled in an ice bath, and a 2 M solution of isopropylmagnesium chloride in THF (11 ml) was added dropwise. After the completion of the dropwise addition, the ice bath was removed and the mixture was stirred for 3 hours, and then cooled again in an ice bath to add tetramethyldiamine (5_5 g). After removing the ice bath and warming to room temperature, 25_2 read bites (4-7 g) and Pd(m3)4 (0.7 g) were added, and 5 hours were mixed at reflux temperature. After cooling the reaction solution to room temperature, EDTA · 4 Ν &amp; water and toluene were added for liquid separation. After the solvent was evaporated under reduced pressure, the obtained solid was purified by column chromatography (eluent: succinyl/acetic acid ethyl s|= 7/3) to obtain 5-di--6'-methyl-2. , 3'-linked 1? than 0, &lt; one 3-〇. Synthesis of the second > 110 201226394 40550pifl For the Chinese manual of No. 140164 No underline correction This amendment is added to the next day of March, 4,4,5,5-tetradecyl-2-(3-(10-( Naphthyl)fluoren-9-yl)phenyl)-1,3,2-dioxaborolane (2 〇, 5_ _6, _ fluorenyl 2,3, _bipyridine (1_2 g) , Pd(PPh3)4 (〇·ΐ5 g), potassium citrate (1.7 g), 1,2,4-trimercaptobenzene 25 m, butanol 5 mi, and water 1 m at reflux temperature After stirring for 5 hours, the reaction liquid was cooled to room temperature, and the precipitated solid was collected by suction filtration, washed with methanol, and then washed with ethyl acetate. Toluene/ethyl acetate = 4/1) Pure deuteration was carried out. The obtained eluate was passed through a short activated carbon tube column to remove the coloring component. The solvent was distilled off under reduced pressure, and the obtained solid was further subjected to chlorobenzene. Recrystallization 'obtained the compound 6 represented by (1-14-15), -mercapto-5-(3-(10(naphthalen-2-yl)fluoren-9-yl)phenyl)-2,3,- Bifluoridine (1.3 g). The structure of the compound was confirmed by NMR measurement. ^-NMR (CDC13): 6 = 9.13 (m, lH), 9.07 (m, lH) , 8.28(dd,lH), 8.01-8.ll(m,3H), 8.00( s,lH), 7.93(m,lH), 7.86( m,lH), 7.73-7.83( m,7H), 7.57 - 7.64 (m, 4H), 7.31-7.39 (m, 4H), 7.28 (d, lH), 2.63 (s, 3H) ° [Synthesis Example 20] Synthesis of Compound (1-14-16) &lt; Synthesis of bromo-5'-fluorenyl 2,3'-bipyridine> A flask to which 3-bromo-5-methylpyridine (3.4 g) and THF (10 ml) were added was cooled in an ice bath. The solution was added dropwise 2 liters of isopropylmagnesium chloride in THF (11 ml). After the addition was completed, 'the ice bath was removed and stirred at room temperature for 1-5 hours, and then cooled again in an ice bath to add zinc chloride tetradecyl. Diamine (5.5 g). After removing the ice bath and warming to room temperature, add 2,5-dactylpyridinium (4.7 g) and Pd(PPh3)4 (0.7 g) 'stirring at reflux temperature 5 111 201226394 40550pifl is the No. 1001·64 Chinese manual without a slash correction. This correction date: March, March, 2011. After the reaction solution was cooled to room temperature, EDTA · 4Na aqueous solution and toluene were added for liquid separation. After the solvent, the obtained solid was purified by silica gel column chromatography (developing solution: toluene / ethyl acetate = 7/3). 5-'; odor-5'-methyl-2,3'-bipyridine (1.4 g) was obtained. &lt;5'-Mercapto-5-(3-(1〇-(naphthyl)fluorenyl-9-yl)phenyl)_2,3,_bipyridinium synthesis&gt; Add 4,4,5,5- Tetramethyl-2-(3-(10-(naphthalen-2-yl)fluoren-9-yl)phenyl)-1,3,2-oxaoxalan (2.0 g), 5-indi- 6,-mercapto-2,3,-combined bite (l_2g), Pd(PPh3)4(〇.15g), iMt^(1.7g), l,2,4*^T base benzene 25 m 5 ml of third butanol and 1 ml of water were scrambled for 5 hours at reflux temperature. After the reaction solution was cooled to room temperature, the precipitated solid was collected by suction filtration, washed with methanol, and washed with ethyl acetate. Subsequently, it was purified by ruthenium column chromatography (developing solution: toluene/ethyl acetate = 4/1), and the obtained eluate was passed through a short activated carbon tube column to remove the colored component. The solvent was distilled off under reduced pressure, and the obtained solid was further recrystallized from gas benzene to obtain the compound 5'-methyl-5-(3-(10-(naphthalene-2) represented by (1-14-16). _ base) 蒽_9_yl)phenyl)_2,3,-biacidine (1.3 g). The structure of the compound was confirmed by NMR measurement. 'H-NMR( CDC13) : δ = 9.08 ( m,lH) , 9.04 ( s,lH) , 8.50 (s,lH) , 8.21 (S,1H) , 8.09 (m,2H) , 8.04 (m,lH ), 8.00 (s, lH), 7.93 (m, lH), 7.73-7.88 (m, 8H), 7.62 (m, 4H), 7.31-7.40 (m, 4H), 2.45 (s, 3H). [Synthesis Example 21] Synthesis of Compound (1-14-17) &lt;Synthesis of 5-Bromo-4'-methyl-2,3'-bipyridine> 112 201226394 Revision date: 丨〇1年3月100Μ0164 Chinese manual without sizing correction The flask to which 3-bromo-4-mercaptopyridine (5 2 g) &amp;THF (1 〇) was added was cooled in an ice bath, and 2M was added dropwise to the solution. Isopropyl chlorided THF solution (17 ml). After the completion of the dropwise addition, the ice bath was removed and the mixture was stirred at room temperature for 9 hours, and then cooled again in the forest, and tetramethylethyleneamine (8.3 g) was added. After removing the ice bath and warming to room temperature, add 2,5-dibromopyrene (7.1 g), Pd-137 (British Johnson Matthey) (〇 4g) and position? (25 ml), stirred at reflux temperature for 6 hours. The reaction solution was cooled to room temperature Ο Ο: EDTA · 4Na aqueous solution and hydrazine were added for liquid separation. After desolvation of the solvent, the obtained solid was purified by Shixi gum column chromatography (developing solution: A = / acetonitrile g = 7 / 3). The mixture was decompressed to remove the solid and the solid was washed with heptane to obtain 5·bromo-4,-mercapto-2,3,-bipyridine (2.4 g). The combination of J4>methyl-5-(3-(1〇•(蔡基)蒽冬基)phenyl)_2,3, ratio. The base 12-yl)®-9-yl)phenylbenzene 25 ml, the second shirt potassium (1.7 g), and 1,2,4-dioxime were mixed for 5 hours. The reaction solution is cooled 5 but 1 2 T plus 'mixed at reflux temperature: toluene / acetic acid acetyl rubber column chromatography (expanded solution is passed into short; secret 2 purified solid obtained, and then obtained The solvent was removed, and the obtained color components were obtained by distillation under reduced pressure (1·14·17). The Q body was further subjected to recrystallization from a toluene towel, and the compound 4L was thiol-5-(3_(10- (naphthalene-2-yl) 113 201226394 40550pifl is the Chinese manual of the 100th M0164 without a slash correction. Amendment date: March 1, 101 蒽-9-yl)phenyl)-2,3'-bipyridine (0.7 g The structure of the compound was confirmed by NMR measurement. 'H-NMR (CDC13): δ = 9.09 ( s, lH) , 8.67 ( s, lH) , 8.51 (d, lH) , 8.09 ( m, 2H) , 8.03 (m,lH) , 8.00 ( m,lH) , 7.93 (m,lH) , 7.88 (d,lH) , 7.73-7.84 (m,6H) , 7.61 (m,4H), 7.52 ( d,lH) , 7.31-7.40 ( m,4H) , 7.23 ( d,lH), 2.46 ( s,3H) ° [Synthesis Example 22] Synthesis of compound (1-14-18) &lt;5-bromo-2'-fluorenyl -2,3·-biacridine synthesis> A flask containing 3-bromo-2-methylpyridine (5_2 g) and THF (10 ml) was cooled in an ice bath, and 2 滴 was added dropwise to the solution. A solution of isopropylmagnesium chloride in THF (17 ml). After the addition was completed, the ice bath was removed and stirred at room temperature for 2 hours, then cooled again in an ice bath, and zinc chloride tetramethylethylenediamine (8.3 g) was added. After removing the ice bath and warming to room temperature, 2,5-dibromopyridine (7.1 g), Pd(PPh3)4 (l.〇g) and diphenylbenzene (l〇ml) were added at reflux temperature. After stirring for 7 hours, the reaction solution was cooled to room temperature, and then an aqueous solution of EDTA • 4Na and a solution were added for liquid separation. After the solvent was distilled off under reduced pressure, the residue was purified by column chromatography (eluent: toluene/ethyl acetate) =4/1) The obtained solid was purified to obtain 5-bromo-2,-mercapto-2,3,-bipyridine (1.3 §). &lt; 2'-mercapto-5-(3-(10- Synthesis of (naphthalen-2-yl)fluoren-9-yl)phenyl)-2,3,-biacridine &gt; Addition of 4,4,5,5-tetramethyl-2-(3_(10_(naphthyl))惹-9-yl)phenyl)-1,3,2-dioxaborolan (2.0 g), 5-bromo-6,-mercapto-2,3'-biacidine (1.2 g) , Pd(PPh3)4 (〇.15g), phosphate (l_7g), 1,2,4-trimethylbenzene 25 m, butanol $ ^1, and water 1 ml, stirred at reflux temperature 114 201226394 40550pifl Revision date: Shu square on March 1 to No. 100,140,164 Chinese amending this specification scoreless stirred for 12 hours. After the reaction solution was cooled to room temperature, toluene and water were added to carry out liquid separation. The solvent was distilled off under reduced pressure, and the obtained solid was purified by silica gel column chromatography (developing solvent: toluene/ethyl acetate = 4/1), and the obtained eluate was passed through a short activated carbon column to remove Coloring ingredients. The solvent was distilled off under reduced pressure, and the precipitated solid was collected by suction filtration to obtain the compound 2'-methyl-5-(3-(10-(naphthalene-2-yl)indole_9-yl) represented by (1_14_18). Phenyl)-2,3'-biacidine (〇.8§). The structure of the compound was confirmed by NMR measurement. ^-NMR (CDCI3): 5 = 9.08 (m, lH), 8.57 (m, lH), 7·99_8.10 (m, 4H), 7.92 (m, lH), 7.88 (d, lH), 7.73 7.83 (m, 7H), 7.61 (m, 4H), 7_51 (dd, lH), 7.30-7.40 (m, 4H), 7.25 (m, lH), 2.66 (s, 3H). [Synthesis Example 23] Synthesis of Compound (1-14-20) &lt;Synthesis of 5-bromo-3'-fluorenyl-2,4'-linked bite&gt; 4-bromo-3-methyl group was added The fr bottle of pyridine (5.0 g) and THF (3 〇ml) was cooled in a dry ice/furanol bath, and 2 M of isopropyl was added dropwise to the solution, and the emulsified magnesium (f) THF (16 ml) was added. After the completion of the dropwise addition, the cooling was removed and the mixture was cooled at room temperature for 2.5 hours, and then cooled in an ice bath to add vaporized tetradecylethylenediamine (8.G g). The ice bath was removed and warmed to room temperature and stirred for 2 hours. After cooling the reaction solution to room temperature, an aqueous solution and an acetic acid acetate (4) were added to separate. After removing the steamed crane and removing the dissolved ^, the residue was obtained by Shixi rubber column chromatography (expansion liquid: toluene / acetic acid ethyl acetate =,,, sputum obtained solid, obtained 5. _3, _ 曱 _2 2 , 4, ♦ than 115 201226394 4〇550pifl No Chinese painting No. 100140164 No picture! J line correction This revision date: March 1, 101 &lt; 3'-methyl-5_(3-(10-(naphthyl) Synthesis of 蒽_9·yl)phenyl)_2,4,_bipyridine&gt; Addition of 4,4,5,5-tetradecyl-2-(3-(10-(naphthalen-2-yl)anthracene -9-yl)phenyl)-1,3,2-dioxaborolan (2.(^), 5-bromo-3,-mercapto-2,4,-bipyridyl (1.2 g) , Pd(PPh3)4 (0.15 g), potassium phosphate (1.7 g), 1,2,4-trimethylbenzene 1 ml, third butanol 1 ml, and water 1 ml, disturbed at reflux temperature 4 After cooling the reaction solution to room temperature, water was added, and the precipitate was collected by suction filtration. The obtained solid was washed with water and decyl alcohol, and then modified with an NH group (DM1020: manufactured by Fuji Chemical Co., Ltd.). Purification by column chromatography (developing solution··toluene) to obtain the compound represented by (1-14-20) 3'-mercapto-5-(3-(1〇-(naphthalene-2-yl))蒽冬基)phenyl)_2,4, _bipyridyl (1.7 g) The structure of the compound was confirmed by NMR measurement. ^-NMRCCDCls: 6 = 9.09 (m, lH), 8.56 (s, lH), 8.55 (d, lH), 8.10 (m, 2H) , 8.03 (m,lH) , 8.00 (d,lH) , 7.93 (d,lH) ,7.88 (d,lH) ,7.73-7.83 (m,6H) ,7.61 (m,4H), 7.53 (d , lH), 7.31-7.41 (m, 5H), 2.44 (s, 3H) ° [Synthesis Example 24] Synthesis of Compound (1-11-18) &lt; 2'-Methyl-5-(6-(10) -Phenylfluoren-9-yl)naphthalen-2-yl)2,3,-linked. Synthesis of pyridines &gt; 4,4,5,5-tetradecyl-2-(6-(10-benzene)蒽-9-yl)naphthalen-2-yl)-1,3,2-dioxaborolan (2.0 g), 5-di-2,-mercapto-2,3'-biacidine ( 1.2g), Pd(PPh3)4(〇_15g), _^_(i.7g), 1,2,4-5T-based benzene (20 ml) 'T-butanol (5ml) and water (iml) Add to flask 116 201226394 40550pifl No. 100140164 Chinese manual without scribe correction This revision date: On March 1, i.i., under a nitrogen atmosphere, 'stirred at reflux temperature for 8 hours. After the completion of the heating, the reaction liquid was cooled to room temperature, and the precipitated solid was collected by suction filtration, washed with decyl alcohol, and washed with ethyl acetate. Subsequently, purification was carried out by means of Shixi rubber column chromatography (developing solution: benzene/ethyl acetate = 7/3), and the obtained eluate was passed through a short activated carbon tube column to remove the coloring component. The solvent was distilled off under reduced pressure. The precipitated solid was collected by suction filtration to obtain the compound 2 represented by (1-11-18), -mercapto-5-(6-(10-phenylfluorenyl) 〇Cai-2 -Base) 2,3'-link. Than bite (1_1 g). The structure of the compound was confirmed by NMR measurement. H-NMR (CDC13): 6 = 9.17 (m,lH), 8.60 (dd,lH) 8.230 (S,1H), 8.19 (m,2H), 8.06 (m,2H), 7.87 (dd,lH): 7.85( dd,lH), 7.73(m,4H), 7.69(dd,lH), 7.55-7.65(m,4H), 7.51 (m,2H) ,7.26-7.37 (m,5H) ,2.73 (s, 3H). The other derivative compound of the present invention can be synthesized by appropriately changing the compound of the starting material and by the method according to the above Synthesis Example. The present invention discloses an example of a money EL element using the compound of the present invention in order to further describe the present invention, but the present invention is not limited thereto. The elements of Examples 1 to 4 and Comparative Examples i to 2 were produced, and the driving start voltage (v) in the strange current driving test and the brightness at which the initial value was maintained at 90% or more were measured (on a small day, DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT EXAMPLES AND COMPARATIVE EXAMPLES— The material compositions of the layers of the fabricated solid m to the example 4 and the comparative (1) to the comparative example 2 are shown in the following Table 1. 117 201226394 40550pifl No. 100140164 Marking correction date of this revision: January 1st, 1st, 1st, 1st, 1st hole, hole injection layer, transmission layer, luminescent layer, electron transport layer, host dopant example 1 HI NPD AB 1-7-74 Example 2 HI NPD AB 1 -7-26 Example 3 HI NPD AB 1-7-98 Example 4 HI NPD AB 1-7-96 Comparative Example 1 HI NPD ABC Comparative Example 2 HI NPD ABD In Table 1, "HI" is N4, N4'- Diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)-[1, fluorene-biphenyl]-4,4,-diamine, "NPD" is N4, N4 '-Di(naphthalen-1-yl)-N4,N4'-diphenyl-[indene, fluorene-biphenyl]-4,4'-diamine, compound (A) is 9-phenyl-10-( 4-phenylnaphthalen-1-yl)anthracene, the compound (Β) is Ν5, Ν5, Ν9, Ν9-7,7-six Η-7Η-benzo[c]indole-5,9-diamine, compound (C) is 9,10-bis([2,2'-biacridinyl]-5-yl)anthracene, compound (D) Is 9,10-bis(4-(acridin-3-yl)naphthalen-1-yl)anthracene. The chemical structure of "Liq" used for the compounds and the layer formed between the electron transport layer and the cathode. It is also revealed as follows: 118 201226394 40550pifl For the 100th Chinese manual of the IOOHOI64, no underline repair ^# Revision date: March 1, 1st 实例 [Example 1] &lt;Component for using compound (1-7-74) for electron transport layer&gt; Grinding IT0 of a film having a thickness of 18 Å by sputtering to 26 mm x 28 mmx at 150 nm A 7 mm glass substrate (manufactured by Opto Science) was used as a transparent supporting substrate. The substrate of the transparent support substrate fixing device (manufactured by Showa Vacuum Co., Ltd.), the cane for the vapor deposition of the compound (4), and the addition of 119 201226394 40550pifl are the Chinese manual of the No. 100140164. Corrected flood season: Molybdenum boat for vapor deposition of compound (B) on March 1, 101, steamed ore with added indium boat, steamed ore with Liq added, and steamed with two-7'74) plus silver A tungsten boat for vapor deposition. The molybdenum boat with magnesium added was added to the ITO film of the transparent supporting substrate, and the vacuum chamber was decompressed to 5xl 〇 4 Pa. First, the chamber was formed into the following layers. The boat was formed to have a thickness of 4 〇 nm by heating: a layer for vapor deposition to which HI was added, and then a method of injecting NPD into the hole to form a hole-transporting layer. 1 a film thickness of 3 〇 nm with compound (4) vapor deposition ❹ and addition; chemicalization; heating added boat 'to the film thickness of 35 nm into the two or two t (B) of the steam mining = two with the compound (8) The weight 'A hair 3 two-tone is the steaming speed. Next, the enthalpy layer of the arsenal plating boat 7.5 having a film thickness of 1 s to _ _74 was heated. The vaporization rate of each layer was _n_small to ~electron formation. Then, the boat film for vapor deposition to which Liq was added was heated. 0.01 πη, /, ^ο.! nm/#^ 1 nm f 〇〇 100 nm by steaming to form a cathode. ^Become m to become a 〇:1 way to adjust the steaming speed, at the base speed = If the ITO electrode is used as the anode and the 〖electron plus DC electric history, then the wavelength is about 46 〇nm == by Obtained the initial bright household 2 (^ 2 bristles first. In addition, the current density of 2000 cd/m is constant 120 201226394 40550pifl is the 100140164 Chinese manual without scribe correction. Revision date: March 1, 101, current drive As a result of the test, the driving start voltage was 7.33 V, and the time for maintaining the luminance of 90% (1800 cd/m 2 ) or more of the initial value was 45 hours. [Example 2] 〇&lt;Component for use of the compound (1-7-26) for the electron transport layer&gt; Except that the compound (1-7-74) was changed to the compound (1-7-26), by the method according to Example 1. An organic EL element was obtained. A constant current driving test was carried out by using an ITO electrode as an anode and a magnesium/silver electrode as a cathode by using a current density for obtaining an initial luminance of 2000 cd/m2. The drive test start voltage was 6.36 V' and the brightness of 90% or more of the initial value was maintained for 151 hours. [Example 3] &lt;Component for using compound (1-7-98) for electron transport layer&gt; Except that compound (1·7_74) was replaced with compound (1-7-98), it was obtained by the method according to Example 1. Organic EL element. A mosquito current driving test was carried out by using a ruthenium electrode as an anode and a silver electrode as a cathode to obtain an initial luminance of 2000 current and a degree. The drive test start voltage is 7 34 V, and the last name is 265 hours. When the brightness of the initial value is kept above [Example 4] The second St material (1丨96) is used for the element of the electron transport layer> The method of rabbit is obtained by changing the compound (1-7·96) Organic EL element. Using the ITO electrode as the 诵d/silver electrode as the cathode ‘by obtaining the initial brightness 2_泰(四)杂性_施, looking for the electricity. Drive; 121 201226394 40550pifl For the 100M0164 Chinese manual without line repair Revision period: March 1, 101 The test start voltage is 5.33 V, 徂 &amp;, between H) 3 hours. When the brightness of 90% or more of the pure value was maintained [Comparative Example 1] = Compound (10) 74) was changed to compound (C) electrode, and magnesium/silver electrode was used; 4 = element. The 1T 〇 electrode is used as the positive cd/m2 wire degree (4) to obtain the initial brightness 2_ starting voltage is 5,06 V, with the 疋 current driving test. The result of the driving test was 6 hours. Keep the silk value of the /. The time of the above brightness [Comparative Example 2] Except that the compound (1_7 7/1, u &amp; according to the method of Example 1 was replaced by the compound (D), the electrode element was used. The 1το electrode was used as the positive C- The current of 2 is used to obtain the initial luminance 2_ starting voltage is 5·ϋΓν, with the H current driving test. The result of the driving test is ίο小时. The time of staying above 9G% of the initial value is summarized in Table 2. . Table 2 122 201226394 ^U33Upill is the Chinese manual of No. 100140164. There is no slash correction. The date of this revision: January 1st, 1st, 1st, 1st and 20th, and the components of the comparative example 3 to the comparative example 5 were measured in the constant current drive test. The driving start voltage (V) and the time (hour) at which the luminance of 90% or more of the initial value is maintained. Hereinafter, examples and comparative examples will be described in detail. The material composition of each of the elements of Examples 5 to 20 and Comparative Examples 3 to 5 produced was not shown in Table 3 below. Table 3 Hole injection layer Hole transport layer Light-emitting layer Electron transport layer Host dopant Example 5 HI HT EF 1-11-1 Example 6 HI HT EF 1-11-2 Example 7 HI HT EF 1-11-3 Example 8 HI HT EF 1-11-4 Example 9 HI HT EF 1-11-5 Example 10 HI HT EF 1-11-39 Example 11 HI HT EF 1-14-2 Example 12 HI HT EF 1-14-3 Example 13 HI HT EF 1-14-11 Example 14 HI HT EF 1-14-12 Example 15 HI HT EF 1-14-14 Example 16 HI HT EF 1-14-15 Example HI HI HT EF 1-14-16 Example 18 HI HT EF 1-14-18 Example 19 HI HT EF 1-14-20 Example 20 HI HT EF 1-11-18 Comparative Example 3 HI HT EFG Comparative Example 4 HI HT EF Η Comparative Example 5 HI HT EFI In 3, HT is Ν-([1,Γ-biphenyl]-4-yl)-9,9-dimercapto 123 201226394 40550pifl is the 100th H0164 Chinese manual without a slash correction. Amendment date: March 101 1-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H--2-amine, compound (E) is 9-(4-(naphthalen-1-yl) Phenyl H0-phenylindole, compound (F) is 4,4,-((7,7-diphenyl-7H-benzo[c]indole-5,9-diyl)bis ((phenyl) Amino))dibenzonitrile, compound (G) is 4'-(4-(1〇- (naphthalen-2-yl)fluoren-9-yl)phenyl)-2,2,:6,,2,,-triazine 0-pyridine, compound (H) is 3-(6-(10-phenylindole) -9-yl)naphthalen-2-yl)pyridinium 'Compound (I) is 6-(4-(10-(naphthalen-1-yl)fluoren-9-yl)phenyl)-2,4,- Bi-bite. [Example 5] 124 201226394 40550pifl Revision date. March 1, 101 is the Chinese manual No. 100M0164 without a sizing correction. &lt;Component (1-11-1) for the element of the electron transport layer&gt; ITO, which was recorded as a film having a thickness of 180 nm, was ground to a glass substrate of 15 μm (manufactured by 〇pt〇^(10) (share)) as a transparent supporting substrate. The transparent branch substrate is fixed to the market of the steaming device (made by Showa Vacuum Co., Ltd.), and the substrate for solidification with HI is used for steaming (4), and the vaporized ore with added ht is compounded with a compound (8). The steamed ore with the chemical compound (i_im) added with silver has a pinned boat, and the town has a steamed ore boat with a film thickness of 40 nm HI. The mine used steam money to form a hole-driving exhibition. A boat for vapor deposition in which the base material (E) having a thickness of 3 nm is added to the base material (E) of the method (E) having a difference of 3 () nm, and a square (F) having a film thickness of 35 nm is simultaneously heated, and Compound (7) = luminescent layer. Take compound = speed. Secondly, at the same time, the method of adjusting tt'l95:5 is used to adjust the evaporation of the boat and the evaporation of Liq with Liq. The evaporation of the material (1-7-1) is carried out in nm/sec~1 nm/sec. A boat for steaming with Llq is added, and the film thickness is t and the electron transport layer is formed to be 25 nm. The steaming speed of each layer is nm 125 201226394 40550pifl The revised flood season: March 1, 101 is the Chinese version of the 100140164 Chinese Wei Ri ^ 乂 manual without the slash correction method at 0.01 nm / %, Λ ^, with, the same The vapor deposition rate of the heart to the second is vapor-deposited. The boat with the silver and the boat with the silver added becomes a cathode with a film thickness of ω : i. At this time, the strip plating speed is adjusted by the original Oimn/# and ~/ of magnesium and silver, and the vapor deposition rate becomes the element. The cathode is formed in a manner of y _ second, and a direct voltage of the organic electroluminescence excitation light is obtained, and a voltage is applied to the anode and the lanthanum/silver as a cathode, thereby obtaining a blue luminescence having a wavelength of about 45 Å. In addition, use:: Obtain the initial brightness of 2 〇〇〇 cd / m2 and implement the 丄 motor drive miscellaneous, rpm test _ electric 4. Start value (10). Cd / m2) above the bright willow ^ [Example 6] T &lt;Component for using compound (1-11 2) for electron transport layer&gt; An organic EL device was obtained by the method according to Example 5 except that the compound was replaced with the compound (1-11·2). Taking the ruthenium electrode as the anode' with the magnesium/(tetra) pole as the cathode, the current is used to obtain the initial bright 2_ cdW. "The mosquito flop test is carried out. The drive starts to test the electricity (4) 4.12 V, maintaining the initial _%% or more. The brightness was 85 hours. [Example 7] &lt;Component for using compound (M1-3) for electron transport layer&gt; In addition to the compound (l-11-i) for compound (M1_3), The organic EL device was obtained by the method of Example 5. The IT 〇 electrode was used as the anode and the magnesium/silver electrode was used as the cathode, and the initial brightness was 126 201226394 40550 pifl. The revised period: March 1, 101, the Chinese manual No. 100140164 The mosquito current was etched without a scribe line correction of $2〇00 cd/m (4). The start voltage of the drive test was 3.78 V. The time for maintaining the brightness of 9 ()% or more of the initial value was 97 hours. [Example 8] <Element for using compound (1_11·4) for electron transport layer> An organic EL device was obtained by the method according to Example 5 except that the compound (1-11-1) was replaced with the compound (M1_4). Using a IT 〇 electrode as an anode, a (10)/silver electrode as a cathode, and a constant current drive test by a current density for obtaining an initial luminance of 2 〇 00 cd/m 2 . The driving test start voltage was 3.95 V', and the time for maintaining the initial (four) 9 ()% or more was 83 hours. [Example 9] <Element for using compound (1-11-5) for electron transport layer> Except that compound G-11·1) was changed to compound (1-11·5), by the method according to Example 5 Obtain an organic el element. A constant current _ test was carried out using a ruthenium electrode as an anode and a silver current _, #(d) at a current density of an initial luminance of 2 〇 00 cd/m. The driving test start voltage was 3.88 V, and the brightness between the %% of the initial value and the remaining value was 93 hours. T [Example 10] <Use of Compound (Ul1·39) for Electron Transport (4) Element> In addition to the compound ((4)), the organic EL element was obtained by the method of Example 5 except that the compound ((4)) was replaced with the compound (1-11-39). . The ITO electrode is used as the anode '(10)/silver electrode as the cathode, and (4) is used to obtain the initial brightness 127 201226394 40550pifl Revision date: March 1st, 1st, March 1st, No. 10014〇164 Chinese manual without line correction 2000 cd/m The current density was used to conduct a mosquito current drive test. The drive test start voltage was 4.16 V, and the brightness of the initial value of 9 ()% or more was maintained for 74 hours. [Example Π] <Element for using the compound (1_14·2) for the electron transport layer> An organic EL element was obtained by the method according to Example 5, except that the compound (i·ΐΜ) was replaced with the compound (Μ4_2). Made with ΙΤ0 electrode For the anode, the magnesium/silver electricity _ rider pole, by (4) to obtain the initial brightness of 2000 cd / m motor money and implement a constant current drive test. The drive test start voltage was 3.61 V, and the brightness of 90% or more of the initial value was maintained for 76 hours. [Example 12] &lt;Component for the use of the compound (1-14 1 , m 4 3) for the electron transport layer&gt; "The compound was replaced by the compound (1), and the organic EL was obtained by the method of Example 5. Component: (5) electrode seven as anode, magnesium/silver electrode as five ^ 2_ cd/m2 current is dense and the cathode is carefully '* is used to obtain the initial bright shoulder test starting voltage is 3.85 νΓ^ 电流 current drive test. Drive 5 words for (4) hours. Keep the value of bribes. (5) [Example 13] The compound (1_14 η λ except for the compound (1 = element for the electron transport layer) is an anode other than the compound (M4_U) according to the method 1 of Example 5, The magnesium/silver electrode is the second organic component. The electrode is used as the cathode, and is used to obtain the initial name 128 201226394 40550pifl. The revised period: March 1, 101 is the 100140164 Chinese manual. (Linear correction The current density of 2000 cd/m2 was used to carry out a constant current drive test. The drive test start voltage was 4.16 V, and the time for maintaining the luminance of 90% or more of the initial value was 162 hours. [Example 14] &lt; M4-12) Element for Electron Transport Layer> An organic EL device was obtained by the method according to Example 5 except that the compound (1-11-1) was replaced with the compound (). , = magnesium / silver electrode as the cathode, by using the initial brightness of 2 〇 00 cd / m2 (four) green ❿ 杂 杂 杂 。 。 。 。 。 。 。 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动 驱动The time is 75 hours. [Example 15] <Element for using the compound (1_14_14) for the electron transport layer> * An organic EL it piece was obtained by the method according to Example 5 except that the compound (1.11) was replaced with the compound (1-14-14). The ITO electrode was used as the %=silver electrode as the cathode, and the constant current driving test was carried out by obtaining the current density of the initial luminance _ CJ^·. The driving test starting voltage was 3 82 V, only 4*, and the flying space was 227. Hour. When the brightness of the initial value is maintained at 90% or more [Example 16] &lt;The compound (κ, v 4-15) is used for the element of the electron transport layer> In addition to the compound Π-ΐι, μ Λ. c, ―1) In addition to the compound (1-14-15), by the method according to the example 5, the magnetic armor is accompanied by β, and the μ-post-extended organic EL element is used as the 1% pole and the magnesium/ The silver electrode is used as the cathode, and is used as the cathode to obtain the initial brightness of 129 201226394 40550pifl. The date of revision: March 1, 101 is the current specification of the 100th IO/I2. Constant current drive test. Drive test starting voltage is 3.98V The time of the brightness of 90% of the initial value was 101 hours. [Example 17] <Component for using the compound (1_14_16) for the electron transport layer> + In addition to the compound (1-14-16) An organic EL element was obtained by the method according to Example 5. The ITO electrode was used as the anode '=magnesium/silver electricity_ as the cathode, and the constant current_test was carried out by the current density of the initial brightness of 2000 cd/m. The drive test start voltage was 4.25 V', and the time to maintain the brightness of 9Q% or more of the initial value was 70 hours. [Example 18] <Element for using the chemical substance (1_14·18) for the electron transport layer> In addition to the compound of the f compound (Bu 14-18), the organic EL it piece was obtained according to the method of Example 5. . Using a tantalum electrode as an anode f magnesium/silver electrode as a cathode, a constant current (four) test was carried out by obtaining an areal density of an initial luminance of 2000 cd/m. The drive test start voltage was 3.75 V, and the brightness of the initial value of 9〇% or more was maintained for 12 5 hours. [Example 19] <Element for using the compound (1·14_2()) for the electron transport layer> "In addition to the compound (W1-1), the compound (1-14-20) was used, and the method according to Example 5 was used. Obtaining an organic EL device, using an ITO electrode as an anode and a magnesium/silver electrode as a cathode, for obtaining an initial luminance 130 201226394 4U55Upifl Revision date: March 1st, 1st, March 1st, No. 100M0164 2_ed/m (four) wire "wire constant current drive test. The drive test start voltage is 4.19 V, and the bright time of 9 G% or more of the initial value is maintained for 63 hours. [Example 20] <Element for using compound (1-11_18) for electron transport layer> An organic EL element was obtained by the method according to Example 5 except that the compound (1-1U1) was replaced with the compound (1-11-18). The IT 〇 electrode is used as the anode, and the silver _ is _, and the constant current drive test is carried out by (4) the current of 6 kW/m at the initial brightness of Weng. The drive test 1 «start voltage is 4.29 V, and the brightness of the initial value of 9Q% or more is maintained for 60 hours. [Comparative Example 3] An organic EL device 1 was obtained by the method according to Example 5 except that the compound (1_1M) was replaced with the compound (G). The electrode was used as the anode 2 and the magnesium/silver electrode was used as the cathode. The initial brightness is 2 ed/m of the electricity money and the actual current axis. County driving test (5) The initial electric power is 5.36 V ‘the initial (four) 9〇% or more brightness time is 2 hours. [Comparative Example 4] An organic el element was obtained by the method according to Example 5, except that the compound (1-11-1) was replaced by the compound (?). The constant current drive test was carried out by using the ιτο electrode as the anode and the magnesium/silver electrode as the cathode, and by obtaining the current density of the initial luminance of 2 〇〇〇 c d/m. As a result, the driving test was started at 4.12 V, and the time for maintaining the brightness of 90% or more of the initial value was 26 hours. 131 201226394 4ϋ55ϋριί1 For the 4th Chinese side of the Dissa, the duck has no underline correction. This revision date: 1 () March 1st of the year [Comparative Example 5] except that the compound (1-11-1) is replaced by the compound (I) The organic EL element was obtained by the method according to Example 5 except for the method. A constant current drive test was carried out by using a ruthenium electrode as the anode '2 with a magnesium/silver electrode as a cathode and a current density for obtaining an initial luminance of 2 〇〇〇 cd/m. As a result, the starting voltage of the driving test was 4.15 V, and the time for maintaining the brightness of 9 % or more of the initial value was 30 hours. The above results are summarized in Table 4. Table 4 Electron transport layer Time to maintain brightness of more than 90% of the initial value: hour) Start voltage (V) 132 201226394 Revision date: March 1, 101 is the first Chinese version of the No. 64 Chinese version of the manual without a slash correction [industrial availability] ϊ 本 this i:: better type, can provide - especially upgrade An organic electroluminescence device having excellent balance between a light-emitting element and a pressure-sensitive component, and a display having the same, and a simple description of the figure, a phantom ', a dynasty, a 忒 、 » » » » » » » » » » 【 【 【 【 【 主要Explanation of symbols] 〇饭0 t 133 201226394 is the first Chinese version of the 1*ί)014〇164 without a slash correction. The date of this amendment is: March 1, 101 invention patent description. (The format and order of this manual, please do not change it. ※Do not fill in the mark ※Application number: ※Application曰: ※Working PC classification: 1. Inventor name: (Chinese/English), electronic transmission material and organic electroluminescent device using it ELECTRON TRANSPORT MATERIAL AND ORGANIC electroluminescent device using ❹ THE SAME II Abstract: The compound represented by the formula (1) of the present invention is an electron transporting material used as an organic EL element, which contributes to the life extension of the organic EL element by using the electron transporting material. In A (1), 'py is independently a group represented by formula (2), (3) or (4); m and n are 0 or 1 'm + n= 1 ; and, in the formula (1), the benzene ring, naphthalene 201226394, date of revision: March 1, 1st, 1st, 100th, 100th, 1st, Chinese, no line correction, this ring And at least one hydrogen on the pyridine ring is substituted with a carbon group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms. 3. The invention is represented by the formula (1) of the present invention is utilized to be an electron transport material of an organic electroluminescent device, and the use of the electron transport material can make contributions like prolonging the life of the organic Electroluminescent device. In formula (1), Py independently represents the group represented by formula (2), (3), or (4); m and n is 0 or 1, m + n= 1; and in formula (1), at least one hydrogen of the benzene ring, naphthalene ring and pyridine ring is replaced by C1-C6 alkyl or C3-C6 cycloalkyl. 201226394 No. 10014〇164 Chinese manual without a slash correction. Amendment date: March 1, 1st, 1st, 7. Patent application scope: 1. A compound represented by the following formula (1). Py is independently a group represented by formula (2), (3) or (4); m^n is 〇 or , 勹 乂 1, m + n = l; and, the carbon number and the at least one nitrogen on the κ ring are taken as a ring number of 3 to 6. (b) or (1-2) the compound described in Table 1, item 1, which is 134 201226394 4U53Uplfl is the Chinese manual of No. 100140164. There is no slash correction. The date of this revision: In the formulas (1-1) and (1-2) of March 1, 1st, Py is the formula (2), (3) or (4) the base represented; (2) (3) (4) Further, at least one hydrogen on the benzene ring, naphthalene ring and η in the formulae (1-1) and (1-2) is substituted with a carbon number of 1 to 6 The alkyl group or a cycloalkyl group having a carbon number of 3 to 6. 3_ The compound of claim 1, which is represented by the following formula (1-3), (1-4), (1-5), or (1-6), In the formulae (1-3) to (1-6), Py is a group represented by the formula (2), (3) or (4); 135 201226394 40550pitl is the Chinese specification of the 100140164 ^ Amendment date: March 1, 1st, and at least one hydrogen on the benzene ring, naphthalene ring and bite ring in formula (1-3)~(1_6) is replaced by Wei to 丨~6 A wire or a ring-burning group having a carbon number of 3 to 6. 4. If applying for a compound as described in item 1 of the full-time, it is expressed by the following formula (1-7) or (1-8). In the formulae (U) and (1-8), py is a group represented by the formula (2), (3) or (4); R is an alkyl group having a carbon number of 1 to 6 or a cycloalkyl group having a carbon number of 3 to 6; and the bridging P is an integer of 1 to 5. The compound described in the first paragraph of the patent application, which has the following formula 136 201226394 ~ T\J^ V/^/xX 1 is the Chinese manual of No. 100140164 without a slash correction. Amendment date: March 1, 1 Day (1-9) or (1-10) means that In the formulas (1-9) and (1-10), Py is a group represented by the formula (2), (3) or (4); 0-0 (2) (3) (4) R is an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms; and q is an integer of 1 to 5. 6. The compound according to claim 1, which is represented by the following formula (1-11) or (1-12), In the formulas (1-11) and (1-12), 137 201226394 Revision date: March 1, 1st is the 10014014 Chinese manual. No scribe correction. Py1 is the formula (2,), (3,) Or the base represented by (4,); In the formulae (2'), (3') and (4,), R is an alkyl group having a carbon number of i to 6 or a cycloalkyl group having a carbon number of 3 to 6, and s is an integer of 丨4. 7. The compound of claim 3, which is represented by the following formula (1-13) or (1-14), In formulas (1-13) and (1-14), Py1 is a group represented by the formula (2,), (3,) or (4,); In f U'), (3') or (4), the ruler is a cyclofilament having an alkyl group having a carbon number of 6 and an inverse number of 3 to 6; and s is an integer of 1 to 4. 8. The compound described in the scope of the patent application is as follows: 138 201226394 Revision date: March 1, 101 is the 100M0164 Chinese manual without a slash correction (1-15) or (ι_16), 〇 〇 In the formulas (Us) and (1-16), Py is a group represented by the formula (2), (3) or (4); (3) (2) (4) = a burnt group having a carbon number of i to 6 or a cycloalkyl group having a carbon number of 3 to 6 and an integer of 1 to 4. 9. The compound described in Patent Application No. 1 Μ, which is represented by U-7-26). (1-7-26) 10. If the patent application formula (1-7-74) indicates the compound described in the first item of the range, it is hereinafter referred to as the following 139 201226394 as the Chinese manual of No. 100-001. March 1st of the following year (1-7-74) η. The compound of claim 1, which is represented by the following formula (1-7-98) (1-7-98) 12 • A compound as described in claim 1 of the patent application, which is represented by the following formula (10) 96) ^ 140 201226394 is the Chinese manual of No. 100140164. There is no slash correction. The date of this amendment is: March 1, 2011. 14. The compound described in claim 1 is the following formula (1-11-1). (1-11_2), (1-11-3), (1-11-4), (1-11-5), (1-11-6), (1-11-8), (1-11 -18), (1-11-39), (1-14-2), (1-14-3), (1-14-11), (1-14-12), (1-14-13) Any one of (1-14-15), (1-14-16), (1-14-17), (1-14-18), and (1-14-20) means: 141 201226394 4U3DUplll For the Chinese manual No. 100140164, there is no slash correction. Amendment date: March 1, 1st, 1st 15. An electron transporting material comprising a compound according to any one of claims 1 to 14. 142 201226394 40550pifl is the Chinese manual of No. 100140164 without a slash correction. Amendment date: March 1, 101 - Money electroluminescent element, including: a counter electrode comprising an anode and a cathode; and disposed on the counter electrode 1 a light-emitting layer; and an electron transport layer and/or an electron injecting sound disposed between the cathode and the light-emitting layer and containing the electron transport material according to claim 15 of the patent application. 17. The organic electro-active excitation according to item 16 of the patent application, wherein at least one of the sub-transport layer and the electron-injecting layer is composed of a ruthenium-based metal complex; And at least one of the group consisting of shed-burning derivatives. The invention relates to the illuminating element of claim 16, wherein the electron transport layer and the electric layer further comprise a vapor selected from the metal of the soil test, the θ, the rare earth metal, 〇 〇 ^ Metal _ _ _ _, the organic complex of the paper in the group: = wrong &amp; and rare earth metal 143 201226394 \ \J Jt ^ l for the 100140164 Chinese manual no line correction Amendment date: March 1st, 1st, 4th, designated representative map (1) The representative representative of the case is: No. (2) The symbol of the symbol of the representative figure is simple: No. 5. If there is a chemical formula in this case , please reveal the chemical formula that best shows the characteristics of the invention: 3