JP2010090034A - 1,3,5-triazine compound, manufacturing method of the same, and organoelectroluminescent element comprising the same as constituent - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an electron-transporting material effective for lowering driving voltage and enhancing luminous efficiency of an organoelectroluminescent element. <P>SOLUTION: The 1,3,5-triazine compound is represented by general formula (1) [wherein R<SP>1</SP>, R<SP>2</SP>and R<SP>3</SP>are each independently a hydrogen atom or a methyl group; V and W are each a carbon atom or a nitrogen atom; and Ar is an optionally substituted aromatic hydrocarbon group]. The organoelectroluminescent element comprises the compound as a constituent thereof. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a 1,3,5-triazine compound, a method for producing the same, and an organic electroluminescent device containing the compound. More particularly, the present invention relates to a 1,3,5-triazine compound having a phenanthrenyl group or a benzoquinolinyl group useful as a component of an organic electroluminescence device and a method for producing the same, and relates to the 1,3,5-triazine compound of the present invention as an organic electroluminescence. By using it in at least one of the organic compound layers of the device, it is possible to reduce the power consumption and extend the life of the organic electroluminescent device.

  An organic electroluminescent element is formed by sandwiching a light-emitting layer containing a light-emitting compound between a hole transport layer and an electron transport layer, and further attaching an anode and a cathode to the outside, and injecting holes and electrons into the light-emitting layer to recombine. It is an element that utilizes light emission (fluorescence or phosphorescence) when excitons that are sometimes generated deactivate. In recent years, organic electroluminescence devices have been attracting attention as the next generation flat panel display, because they can be made thinner and lighter, they are self-luminous devices, have low power consumption, and have a simple device structure. Therefore, the manufacturing cost is low. The manufacturing method can be applied to various manufacturing techniques such as vacuum deposition, spin coating, ink jet, offset printing, thermal transfer, and the like. Currently, portable devices such as mobile phones, portable music devices, and PDAs (Personal Digital Assistants) have been put into practical use, but if larger size and higher definition are achieved, not only flat panel displays but also surface emitting light sources It is possible to expand to lighting, paper-like display using flexible characteristics, wearable display, see-through display using transparency, etc., and the market is expected to expand rapidly.

  However, there are still many technical issues that must be overcome. Particularly, in the present situation, the drive voltage is high and the efficiency is low, so that the power consumption is high. At the same time, a high driving voltage can cause a short life of the device.

  This problem is caused by insufficient properties of materials constituting the organic electroluminescent element, particularly electron transport materials. A wide variety of hole transport materials are known, mainly triarylamine derivatives, but there are few reported examples of electron transport materials. Tris (8-quinolinolato) aluminum (III) (Alq) is a material that has already been put into practical use, but hole transport materials such as N, N′-bis (1-naphthyl) -N, N′-diphenyl- Since the performance is lower than that of 4,4′-biphenyl (NPD), the characteristics of the organic electroluminescent device are limited.

  Examples of reports of other electron transport materials include oxadiazole derivatives (Patent Document 1), quinoxaline derivatives (Patent Document 2), triazole derivatives (Patent Document 3), silacyclopentadiene derivatives (Patent Document 4), quinoline derivatives ( Patent Document 5), benzimidazole derivatives (Patent Document 6), benzothiazole derivatives (Non-Patent Document 1), and the like. However, there are many practical problems such as high driving voltage, easy thin film crystallization, and short life.

  The 1,3,5-triazine compound of the present invention is characterized by having one 3,5-disubstituted phenyl group at the 2-position of the triazine ring, and two aromatic hydrocarbon groups at the 4,6-position. It is characterized by having.

  Recently, examples in which 1,3,5-triazine compounds are used in organic electroluminescent devices are disclosed in Patent Documents 7 and 8, which are triazine derivatives having a benzoazole moiety at the 2,4,6 positions of the triazine ring. It is completely different from the 1,3,5-triazine compound of the present invention.

  Patent Documents 9 to 12 disclose examples in which 1,3,5-triazine derivatives are used in organic electroluminescent devices, but these triazine derivatives are located at positions 2, 4, and 6 of the triazine ring. A 1,3,5-triazine compound of the present invention having a 3,5-disubstituted phenyl group in that it has a 3,4-disubstituted phenyl group or a 3,4-disubstituted phenyl group Is different.

  Patent Document 13 discloses an example in which a 1,3,5-triazine derivative is used for an organic electroluminescent device. These are aromatic heterocyclic groups at all of the 2, 4, and 6 positions of the triazine ring. Is a triazine derivative having a substituted aromatic hydrocarbon group, which is completely different from the 1,3,5-triazine compound of the present invention.

  Further, on page 27 of Patent Document 14, only one example of a 1,3,5-triazine derivative (Compound No. C-8) used for an organic electroluminescent device is exemplified. It is a triazine derivative having the same aromatic hydrocarbon group at the 4th and 6th positions, which is completely different from the 1,3,5-triazine compound of the present invention.

  Further, on page 8 of Patent Document 15, only one example of a 1,3,5-triazine derivative (Compound No. 1) used for an organic electroluminescence device is exemplified, but this is a 2,4,4 of triazine ring. This is a triazine derivative having the same 4-monosubstituted phenyl group at the 6-position, which is completely different from the 1,3,5-triazine compound of the present invention.

  Patent Document 16 discloses an example in which a 1,3,5-triazine derivative is used in an organic electroluminescence device, but the 2,4,6 positions of these triazine rings are substituted with a monosubstituted phenyl group. And is different from the 1,3,5-triazine compound of the present invention characterized by having a 3,5-disubstituted phenyl group.

  Patent Document 17 discloses an example in which a 1,3,5-triazine derivative is used for an organic electroluminescent device, but the position of the substituent on the 2,4,6-position phenyl group of the triazine ring is as follows. The 1,3,5-triazine compound of the present invention, which is not limited and has a 3,5-disubstituted phenyl group, is not specifically shown.

JP-A-6-136359 JP-A-6-207169 International Publication No. 95/25097 Pamphlet JP 2005-104986 A JP 2006-199677 A International Publication No. 2004/080975 Pamphlet JP-A-7-157473 Japanese Patent Laid-Open No. 2003-303690 US Pat. No. 6,057,048 US Pat. No. 6,229,012 US Pat. No. 6,225,467 JP 2004-63465 A JP 2003-45662 A JP 2001-143869 A JP 2003-282270 A Japanese Patent No. 4106974 JP 2007-137829 A Applied Physics Letters, 89, 063504, 2006

  The present invention provides a 1,3,5-triazine compound having a novel structure that enables low-voltage driving of an element as an electron transport layer of an organic electroluminescent element, and further has a long life using the compound. An organic electroluminescent device is provided.

  As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that the 1,3,5-triazine compound (1) of the present invention is amorphous by either vacuum deposition or spin coating. A thin film can be formed, and organic electroluminescence devices using these as an electron transport layer can achieve lower power consumption and longer life than general-purpose organic electroluminescence devices. It came to do.

  That is, the present invention relates to the general formula (1)

[Wherein, R ¹ , R ² and R ³ each independently represents a hydrogen atom or a methyl group. V and W represent a carbon atom or a nitrogen atom. Ar represents an optionally substituted aromatic hydrocarbon group. ]
It is related with the 1,3,5-triazine compound shown by these.

  The present invention also provides a general formula (2)

[In formula, V and W represent a carbon atom or a nitrogen atom. M represents ZnR ⁴ , MgR ⁵ , Sn (R ⁶ ) ₃ , B (OR ⁷ ) ₂ . However, R < ⁴ > and R < ⁵ > respectively independently represents a chlorine atom, a bromine atom, or an iodine atom, R < ⁶ > represents a C1-C4 alkyl group or a phenyl group, R < ⁷ > is a hydrogen atom, C1-C1 4 represents an alkyl group or a phenyl group, and R ⁶ and R ⁷ may be the same or different from each other. Two R ⁷ can also form a ring integrally with a boron atom bonded through an oxygen atom. ]
And a compound of the general formula (3)

[Wherein, R ¹ , R ² and R ³ each independently represents a hydrogen atom or a methyl group. Ar represents an optionally substituted aromatic hydrocarbon group. Y ¹ represents a chlorine atom, a bromine atom, an iodine atom or a trifluoromethanesulfoxy group. ]
A method for producing a 1,3,5-triazine compound represented by the general formula (1), wherein the compound represented by formula (1) is subjected to a coupling reaction in the presence or absence of a base in the presence of a palladium catalyst. It is about.

  The present invention also provides a general formula (4)

[In formula, V and W represent a carbon atom or a nitrogen atom. Y ² represents a chlorine atom, a bromine atom, an iodine atom or a trifluoromethanesulfoxy group. ]
And a compound of the general formula (5)

[Wherein, R ¹ , R ² and R ³ each independently represents a hydrogen atom or a methyl group. Ar represents an optionally substituted aromatic hydrocarbon group. R ⁷ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group, and R ⁷ may be the same or different from each other. Two R ⁷ can also form a ring integrally with a boron atom bonded through an oxygen atom. ]
The present invention relates to a process for producing a 1,3,5-triazine compound represented by the general formula (1), characterized in that a coupling reaction is carried out in the presence of a base and a palladium catalyst.

  Furthermore, this invention relates to the organic electroluminescent element characterized by using the 1,3,5-triazine compound shown by General formula (1) as a structural component.

  Hereinafter, the present invention will be described in detail.

R ¹ , R ^2, and R ³ each independently represent a hydrogen atom or a methyl group, and a hydrogen atom is preferable in terms of good performance as a material for an organic electroluminescent device.

  Examples of the optionally substituted aromatic hydrocarbon group represented by Ar include an optionally substituted phenyl group or an optionally substituted naphthyl group.

  Examples of the optionally substituted phenyl group represented by Ar include a phenyl group, a p-tolyl group, an m-tolyl group, an o-tolyl group, a p-trifluoromethylphenyl group, an m-trifluoromethylphenyl group, o-trifluoromethylphenyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group, mesityl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,4-diethyl Phenyl group, 3,5-diethylphenyl group, 2-propylphenyl group, 3-propylphenyl group, 4-propylphenyl group, 2,4-dipropylphenyl group, 3,5-dipropylphenyl group, 2-isopropyl Phenyl group, 3-isopropylphenyl group, 4-isopropylphenyl group, 2,4-diisopropylphenyl group, 3,5-diisopropyl Pyrphenyl group, 2-butylphenyl group, 3-butylphenyl group, 4-butylphenyl group, 2,4-dibutylphenyl group, 3,5-dibutylphenyl group, 2-tert-butylphenyl group, 3-tert-butyl Phenyl group, 4-tert-butylphenyl group, 2,4-di-tert-butylphenyl group, 3,5-di-tert-butylphenyl group, biphenyl-4-yl group, biphenyl-3-yl group, biphenyl 2-yl group, 2-methylbiphenyl-4-yl group, 3-methylbiphenyl-4-yl group, 2′-methylbiphenyl-4-yl group, 4′-methylbiphenyl-4-yl group, 2, 2'-dimethylbiphenyl-4-yl group, 2 ', 4', 6'-trimethylbiphenyl-4-yl group, 6-methylbiphenyl-3-yl group, 5-methyl Phenyl-3-yl group, 2′-methylbiphenyl-3-yl group, 4′-methylbiphenyl-3-yl group, 6,2′-dimethylbiphenyl-3-yl group, 2 ′, 4 ′, 6 ′ -Trimethylbiphenyl-3-yl group, 5-methylbiphenyl-2-yl group, 6-methylbiphenyl-2-yl group, 2'-methylbiphenyl-2-yl group, 4'-methylbiphenyl-2-yl group 6,2′-dimethylbiphenyl-2-yl group, 2 ′, 4 ′, 6′-trimethylbiphenyl-2-yl group, 2-trifluoromethylbiphenyl-4-yl group, 3-trifluoromethylbiphenyl- 4-yl group, 2′-trifluoromethylbiphenyl-4-yl group, 4′-trifluoromethylbiphenyl-4-yl group, 6-trifluoromethylbiphenyl-3-yl group, 5-trifluoro Fluoromethylbiphenyl-3-yl group, 2′-trifluoromethylbiphenyl-3-yl group, 4′-trifluoromethylbiphenyl-3-yl group, 5-trifluoromethylbiphenyl-2-yl group, 6- Trifluoromethylbiphenyl-2-yl group, 2′-trifluoromethylbiphenyl-2-yl group, 4′-trifluoromethylbiphenyl-2-yl group, 3-ethylbiphenyl-4-yl group, 4′-ethyl Biphenyl-4-yl group, 2 ′, 4 ′, 6′-triethylbiphenyl-4-yl group, 6-ethylbiphenyl-3-yl group, 4′-ethylbiphenyl-3-yl group, 5-ethylbiphenyl- 2-yl group, 4′-ethylbiphenyl-2-yl group, 2 ′, 4 ′, 6′-triethylbiphenyl-2-yl group, 3-propylbiphenyl-4-yl 4'-propylbiphenyl-4-yl group, 2 ', 4', 6'-tripropylbiphenyl-4-yl group, 6-propylbiphenyl-3-yl group, 4'-propylbiphenyl-3-yl group 5-propylbiphenyl-2-yl group, 4′-propylbiphenyl-2-yl group, 2 ′, 4 ′, 6′-tripropylbiphenyl-2-yl group, 3-isopropylbiphenyl-4-yl group, 4′-isopropylbiphenyl-4-yl group, 2 ′, 4 ′, 6′-triisopropylbiphenyl-4-yl group, 6-isopropylbiphenyl-3-yl group, 4′-isopropylbiphenyl-3-yl group, 5-isopropylbiphenyl-2-yl group, 4′-isopropylbiphenyl-2-yl group, 2 ′, 4 ′, 6′-triisopropylbiphenyl-2-yl group, 3-butyl Rubiphenyl-4-yl group, 4′-butylbiphenyl-4-yl group, 2 ′, 4 ′, 6′-tributylbiphenyl-4-yl group, 6-butylbiphenyl-3-yl group, 4′-butyl Biphenyl-3-yl group, 5-butylbiphenyl-2-yl group, 4′-butylbiphenyl-2-yl group, 2 ′, 4 ′, 6′-tributylbiphenyl-2-yl group, 3-tert-butyl Biphenyl-4-yl group, 4′-tert-butylbiphenyl-4-yl group, 2 ′, 4 ′, 6′-tri-tert-butylbiphenyl-4-yl group, 6-tert-butylbiphenyl-3- Yl group, 4'-tert-butylbiphenyl-3-yl group, 5-tert-butylbiphenyl-2-yl group, 4'-tert-butylbiphenyl-2-yl group, 2 ', 4', 6'- Tri-t An ert-butylbiphenyl-2-yl group and the like can be mentioned. A phenyl group, a p-tolyl group, an m-tolyl group, an o-tolyl group, a 4-butylphenyl group, a 4-tert-butylphenyl group, a biphenyl-4-group, in terms of good performance as a material for an organic electroluminescent device. An yl group and a biphenyl-3-yl group are preferable, and a phenyl group, a p-tolyl group, and a biphenyl-3-yl group are more preferable in terms of easy synthesis.

  Examples of the optionally substituted naphthyl group represented by Ar include 1-naphthyl group, 4-methylnaphthalen-1-yl group, 4-trifluoromethylnaphthalen-1-yl group, 4-ethylnaphthalene- 1-yl group, 4-propylnaphthalen-1-yl group, 4-butylnaphthalen-1-yl group, 4-tert-butylnaphthalen-1-yl group, 5-methylnaphthalen-1-yl group, 5-tri Fluoromethylnaphthalen-1-yl group, 5-ethylnaphthalen-1-yl group, 5-propylnaphthalen-1-yl group, 5-butylnaphthalen-1-yl group, 5-tert-butylnaphthalen-1-yl group 2-naphthyl group, 6-methylnaphthalen-2-yl group, 6-trifluoromethylnaphthalen-2-yl group, 6-ethylnaphthalen-2-yl group, 6- Lopylnaphthalen-2-yl group, 6-butylnaphthalen-2-yl group, 6-tert-butylnaphthalen-2-yl group, 7-methylnaphthalen-2-yl group, 7-trifluoromethylnaphthalene-2- Yl group, 7-ethylnaphthalen-2-yl group, 7-propylnaphthalen-2-yl group, 7-butylnaphthalen-2-yl group, 7-tert-butylnaphthalen-2-yl group and the like. 1-naphthyl group, 4-methylnaphthalen-1-yl group, 4-tert-butylnaphthalen-1-yl group, 5-methylnaphthalen-1-yl group in terms of good performance as a material for organic electroluminescent elements 5-tert-butylnaphthalen-1-yl group, 2-naphthyl group, 6-methylnaphthalen-2-yl group, 6-tert-butylnaphthalen-2-yl group, 7-methylnaphthalen-2-yl group or A 7-tert-butylnaphthalen-2-yl group is preferable, and a 2-naphthyl group is more preferable in terms of easy synthesis.

  Next, the manufacturing method of this invention is demonstrated.

  Preferable examples of the compound represented by the general formula (2) include the following basic skeletons (I) to (IV), but the present invention is not limited thereto.

Examples of ZnR ⁴ and MgR ⁵ represented by M include ZnCl, ZnBr, ZnI, MgCl, MgBr, and MgI. ZnCl is preferable in that the reaction yield is good.

Examples of Sn (R ⁶ ) ₃ represented by M include SnMe ₃ and SnBu ₃ .

Examples of B (OR ⁷ ) ₂ represented by M include B (OH) ₂ , B (OMe) ₂ , B (O (iso-Pr)) ₂ , and B (OBu) ₂ .

In B ^(OR _{7) 2} represented by M, as an example of B of ^(OR _{7) 2} If two ^{R 7} formed a ring together with the boron atom is attached via an oxygen atom, the following The groups represented by (V) to (X) can be exemplified, and the group represented by (VI) is preferable in that the reaction yield is good.

Examples of Y ¹ include a chlorine atom, a bromine atom, an iodine atom, or a trifluoromethanesulfoxy group, and a bromine atom is preferable from the viewpoint of good reaction yield and selectivity.

  Preferable examples of the compound represented by the general formula (4) include the following basic skeletons (XI) to (XIV), but the present invention is not limited thereto.

Examples of Y ² include a chlorine atom, a bromine atom, an iodine atom, and a trifluoromethanesulfoxy group, and a bromine atom is preferable from the viewpoint of good reaction yield and selectivity.

  The 1,3,5-triazine compound (1) of the present invention has the following reaction formula:

[Wherein, R ¹ , R ² , R ³ , V, W, Y ¹ , Ar and M are the same as described above. ]
It can manufacture by the method shown by.

  In “Step 1”, the compound (2) is reacted with the compound (3) in the presence or absence of a base in the presence of a palladium catalyst to produce the 1,3,5-triazine compound (1) of the present invention. The target product is obtained with good reaction yield by applying reaction conditions and catalysts of general coupling reactions such as Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada reaction, Stille reaction, etc. be able to. The molar ratio between the palladium catalyst used in the reaction and the compound (3) is preferably 1: 200 to 1: 2, and more preferably 1: 100 to 1:10 in terms of good reaction yield.

  Examples of the palladium catalyst that can be used in “Step 1” include salts of palladium chloride, palladium acetate, palladium trifluoroacetate, palladium nitrate, and the like. Furthermore, π-allyl palladium chloride dimer, palladium acetylacetonate, tris (dibenzylideneacetone) dipalladium, dichlorobis (triphenylphosphine) palladium, tetrakis (triphenylphosphine) palladium and dichloro [1,1′-bis (diphenylphosphine). Fino) ferrocene] complex compounds such as palladium. Palladium chloride, palladium acetate, tris (dibenzylideneacetone) dipalladium, dichlorobis (triphenylphosphine) palladium, and tetrakis (triphenylphosphine) palladium are preferred because they are easily available and have a good reaction yield. Among these, a palladium complex having a tertiary phosphine as a ligand is more preferable in terms of a good reaction yield. The palladium complex having such a tertiary phosphine as a ligand can also be prepared in a reaction system by adding a tertiary phosphine to a palladium salt or a complex compound.

  The tertiary phosphine that can be used at this time is triphenylphosphine, trimethylphosphine, tributylphosphine, tri (tert-butyl) phosphine, tricyclohexylphosphine, tert-butyldiphenylphosphine, 9,9-dimethyl-4,5. -Bis (diphenylphosphino) xanthene, 2- (diphenylphosphino) -2 '-(N, N-dimethylamino) biphenyl, 2- (di-tert-butylphosphino) biphenyl, 2- (dicyclohexylphosphino) Biphenyl, bis (diphenylphosphino) methane, 1,2-bis (diphenylphosphino) ethane, 1,3-bis (diphenylphosphino) propane, 1,4-bis (diphenylphosphino) butane, 1,1 ′ -Bis (diphenylphosphino) Erocene, tri (2-furyl) phosphine, tri (o-tolyl) phosphine, tris (2,5-xylyl) phosphine, (±) -2,2′-bis (diphenylphosphino) -1,1′-binaphthyl And 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl. Triphenylphosphine, 1,1′-bis (diphenylphosphino) ferrocene, and 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl are preferable because they are easily available and the reaction yield is good. . The molar ratio of the tertiary phosphine to be used and the palladium salt or complex compound is preferably 1:10 to 10: 1, and more preferably 1: 2 to 5: 1 in terms of a good reaction yield.

  Bases that can be used in “Step 1” include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, potassium phosphate, sodium phosphate, sodium fluoride, potassium fluoride, fluorine. Cesium carbonate etc. can be illustrated and a cesium carbonate is preferable at a point with a sufficient reaction yield. The molar ratio of the base and the compound (2) is preferably 1: 2 to 10: 1, and more preferably 1: 1 to 3: 1 in terms of good reaction yield.

  The molar ratio of the compound (2) and the compound (3) used in “Step 1” is preferably 1: 1 to 5: 1, and more preferably 2: 1 to 3: 1 in terms of good reaction yield.

  Examples of the solvent that can be used in “Step 1” include water, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, toluene, benzene, diethyl ether, and xylene, and these may be used in appropriate combination. Tetrahydrofuran is preferably used from the viewpoint of good reaction yield.

  The reaction of “Step 1” can be carried out at a temperature appropriately selected from the range of 0 ° C. to 150 ° C., and more preferably in the range of 50 ° C. to 120 ° C. in terms of a good reaction yield.

  Compound (1) can be obtained by performing a normal treatment after completion of “Step 1”. If necessary, it may be purified by recrystallization, column chromatography or sublimation.

  Next, the compound (2) which is a raw material of “Step 1” for producing the 1,3,5-triazine compound (1) of the present invention is represented by the following reaction formula, for example.

[Wherein, R ⁷ , V, W and M are the same as defined above. Y ³ represents a chlorine atom, a bromine atom, an iodine atom or a trifluoromethanesulfoxy group. L represents a leaving group. ]
It can manufacture by the method shown by.

  “Step 2” is a step of reacting a compound represented by the general formula (4a) with a lithium reagent to obtain a lithium compound represented by the general formula (4b). The compound (4b) obtained in “Step 2” may be isolated after the reaction or may be subjected to “Step 3” without isolation.

  The lithium reagent used in “Step 2” is preferably butyllithium or tert-butyllithium from the viewpoint of good reaction yield. The molar ratio of the lithium reagent to the compound (4a) is preferably 1: 1 to 5: 1, and more preferably 1: 1 to 3: 1 in that the reaction yield is particularly good.

  Examples of the solvent that can be used in the reaction in “Step 2” include tetrahydrofuran, toluene, benzene, diethyl ether, xylene, and the like, and these may be used in appropriate combination. Tetrahydrofuran is preferably used from the viewpoint of good reaction yield.

  The reaction of “Step 2” can be carried out at a temperature appropriately selected from the range of −150 ° C. to −20 ° C., and the range of −100 ° C. to −60 ° C. is more preferable in terms of good reaction yield.

Compound (4a) can be easily obtained, for example, by a coupling reaction using a general-purpose metal catalyst described in Non-Patent Document 2. Y ³ can be exemplified by a chlorine atom, a bromine atom, an iodine atom, a trifluoromethanesulfoxy group, or the like, but a bromine atom is preferable in terms of a good reaction yield.

  “Step 3” is a step of producing the compound represented by the general formula (2) used in “Step 1” by reacting the lithium compound (4b) with the coupling reagent represented by the general formula (6). is there. The compound (2) obtained in “Step 3” may be isolated after the reaction or may be subjected to “Step 1” without isolation.

  The coupling reagent (6) used in “Step 3” includes dichloro (tetramethylethylenediamine) zinc (II), zinc chloride, zinc bromide, zinc iodide, trimethyltin chloride, tributyltin chloride, trimethylborate, Triisopropyl borate, (2,3-dimethylbutane-2,3-dioxy) methoxyborane, (2,3-dimethylbutane-2,3-dioxy) isopropoxyborane, 1,3-propanedioxyborane, etc. It can be illustrated. Dichloro (tetramethylethylenediamine) zinc (II), trimethyl borate, triisopropyl borate, (2,3-dimethylbutane-2,3-dioxy) isopropoxyborane are preferable in terms of easy handling, and the reaction yield Of these, dichloro (tetramethylethylenediamine) zinc (II) is more preferable. Examples of the leaving group represented by L include Cl, Br, I, MeO, and iso-PrO. The molar ratio of the coupling reagent (6) to the compound (4b) is preferably 1: 1 to 10: 1, and more preferably 1.5: 1 to 3: 1 in terms of good reaction yield.

  The reaction of “Step 3” can be carried out at a temperature appropriately selected from the range of −150 ° C. to 50 ° C., and more preferably carried out in the range of −100 ° C. to 30 ° C. in terms of good reaction yield. .

  In “Step 4”, the compound (4a) is reacted with a borane compound represented by the general formula (7) or a diboron compound represented by the general formula (8) in the presence of a base and a palladium catalyst. In this step, the compound (2a) used in 1) is produced. For example, by applying the reaction conditions and catalyst disclosed in Non-Patent Document 3 or 4, the target product can be obtained with good reaction yield. The molar ratio of the palladium catalyst to the compound (4a) is preferably 1: 200 to 1: 2, and more preferably 1:50 to 1:10 in terms of a good reaction yield. The obtained compound (2a) may be isolated after the reaction or may be subjected to “Step 1” without isolation.

  Examples of the palladium catalyst that can be used in “Step 4” include the palladium catalysts exemplified in “Step 1”, but palladium chloride, palladium acetate, tris is preferable because they are easily available and the reaction yield is good. (Dibenzylideneacetone) dipalladium, dichlorobis (triphenylphosphine) palladium, tetrakis (triphenylphosphine) palladium, dichloro [1,1′-bis (diphenylphosphino) ferrocene] palladium are preferred, and tertiary phosphine is particularly preferable. Palladium complexes possessed as ligands are preferred in that the reaction yield is good. Moreover, the palladium complex which has these tertiary phosphine as a ligand can also add a tertiary phosphine to a palladium salt or a complex compound, and can also prepare it in a reaction system. As the tertiary phosphine that can be used in this case, the tertiary phosphine exemplified in “Step 1” can be mentioned. However, triphenylphosphine, 1, 1'-bis (diphenylphosphino) ferrocene is preferred. The molar ratio between the tertiary phosphine and the palladium salt or complex compound is preferably 1:10 to 10: 1, and more preferably 1: 2 to 5: 1 in terms of good reaction yield.

  Examples of the base that can be used in “Step 4” include the bases exemplified in “Step 1”, and potassium carbonate and cesium carbonate are preferable in terms of a good reaction yield. The molar ratio of the base and the compound (4a) is preferably 1: 2 to 10: 1, and more preferably 1: 1 to 3: 1 in terms of good reaction yield.

  The molar ratio of the borane compound (7) or diboron compound (8) and the compound (4a) used in “Step 4” is preferably 1: 1 to 5: 1, and 1: 1 to 3 in that the reaction yield is good. : 1 is more preferred.

  Examples of the solvent that can be used in “Step 4” include dimethyl sulfoxide, N, N-dimethylformamide, tetrahydrofuran, toluene, benzene, diethyl ether, and xylene, and these may be used in appropriate combination. N, N-dimethylformamide or dimethyl sulfoxide is preferably used from the viewpoint of good reaction yield.

  The reaction of “Step 4” can be carried out at a temperature appropriately selected from the range of 0 ° C. to 150 ° C., and more preferably in the range of 50 ° C. to 120 ° C. in terms of good reaction yield.

  Compound (2a) can be obtained by performing a usual treatment after completion of “Step 4”. If necessary, it may be purified by recrystallization, column chromatography or sublimation.

  The compound represented by the general formula (3) can be produced, for example, according to the method of Patent Document 18.

  Furthermore, the 1,3,5-triazine compound (1) of the present invention has the following reaction formula:

[Wherein, R ¹ , R ² , R ³ , R ⁷ , V, W, Y ² and Ar are the same as described above. ]
It can also be manufactured by the method shown in.

  “Step 5” is a step for producing the 1,3,5-triazine compound (1) of the present invention by reacting compound (5) with compound (4) in the presence of a base and a palladium catalyst. By applying the reaction conditions and catalyst of the typical Suzuki-Miyaura reaction, the target product can be obtained with good reaction yield. The molar ratio of the palladium catalyst to the compound (5) is preferably 1: 200 to 1: 2, and more preferably 1: 100 to 1:10 in terms of a good reaction yield.

  Examples of the palladium catalyst that can be used in “Step 5” include the palladium catalyst exemplified in “Step 1”, but palladium chloride, palladium acetate, and dichlorobis are easily available and have good reaction yield. (Triphenylphosphine) palladium is preferable, and among them, a palladium complex having a tertiary phosphine as a ligand is preferable in terms of a good reaction yield. These palladium complexes can also be prepared in a reaction system by adding a tertiary phosphine to a palladium salt or complex compound. As the tertiary phosphine that can be used in this case, the tertiary phosphine exemplified in “Step 1” can be exemplified, but triphenylphosphine is preferable because it is easily available and the reaction yield is good. The molar ratio between the tertiary phosphine and the palladium salt or complex compound is preferably 1:10 to 10: 1, and more preferably 1: 2 to 5: 1 in terms of good reaction yield.

  Examples of the base that can be used in “Step 5” include the bases exemplified in “Step 1”, but cesium carbonate is preferable in that the reaction yield is good. The molar ratio of the base and the compound (4) is preferably 1: 2 to 10: 1, and more preferably 1: 1 to 3: 1 in terms of a good reaction yield.

  The molar ratio of the compound (4) and the compound (5) used in “Step 5” is preferably 2: 1 to 5: 1, and more preferably 2: 1 to 3: 1 in terms of a good reaction yield.

  Examples of the solvent that can be used in “Step 5” include water, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, toluene, benzene, diethyl ether, and xylene, and these may be used in appropriate combination. Tetrahydrofuran is preferably used from the viewpoint of good reaction yield.

  The reaction of “Step 5” can be performed at a temperature appropriately selected from the range of 0 ° C. to 150 ° C., and is preferably performed in the range of 50 ° C. to 120 ° C. in terms of a good reaction yield.

  Compound (1) can be obtained by performing a normal treatment after completion of “Step 5”. If necessary, it may be purified by recrystallization, column chromatography or sublimation.

  Next, the compound (5) which is the raw material of “Step 5” for producing the 1,3,5-triazine compound (1) of the present invention is represented by the following reaction formula, for example.

[Wherein, R ¹ , R ² , R ³ , R ⁷ , Y ¹ and Ar are the same as defined above. ]
It can manufacture by the method shown by.

  In “Step 6”, Compound (3) used in “Step 5” is produced by reacting Compound (3) with borane compound (7) or diboron compound (8) in the presence of a base and a palladium catalyst. For example, by applying the reaction conditions and catalyst disclosed in Non-Patent Document 3 or 4, the target product can be obtained with good reaction yield. The molar ratio of the palladium catalyst to the compound (3) is preferably 1: 200 to 1: 2, and more preferably 1: 100 to 1:10 in terms of a good reaction yield. The obtained compound (5) may be isolated after the reaction, but may be subjected to “Step 5” without isolation.

  Examples of the palladium catalyst that can be used in “Step 6” include the palladium catalysts exemplified in “Step 1”, but palladium chloride, palladium acetate, and dichlorobis are easily available and have good reaction yield. (Triphenylphosphine) palladium and dichloro [1,1′-bis (diphenylphosphino) ferrocene] palladium are preferable, and among them, a palladium complex having a tertiary phosphine as a ligand is preferable in terms of a good reaction yield. These palladium complexes can also be prepared in a reaction system by adding a tertiary phosphine to a palladium salt or complex compound. As the tertiary phosphine that can be used in this case, the tertiary phosphine exemplified in “Step 1” can be mentioned. However, triphenylphosphine, 1, 1'-bis (diphenylphosphino) ferrocene is preferred. The molar ratio between the tertiary phosphine and the palladium salt or complex compound is preferably 1:10 to 10: 1, and more preferably 1: 2 to 5: 1 in terms of good reaction yield.

  Examples of the base that can be used in “Step 6” include the bases exemplified in “Step 1”, but potassium acetate is preferable in terms of good reaction yield. The molar ratio of the base and the compound (3) is preferably 1: 2 to 10: 1, and more preferably 1: 1 to 3: 1 in terms of a good reaction yield.

  The molar ratio of the borane compound (7) or diboron compound (8) and the compound (3) used in “Step 6” is preferably 1: 1 to 5: 1 and 2: 1 to 4 in that the reaction yield is good. : 1 is more preferred.

  Examples of the solvent that can be used in “Step 6” include dimethyl sulfoxide, tetrahydrofuran, toluene, benzene, diethyl ether, and xylene, and these may be used in appropriate combination. Tetrahydrofuran is preferably used from the viewpoint of good reaction yield.

  The reaction of “Step 6” can be performed at a temperature appropriately selected from the range of 0 ° C. to 150 ° C., and is preferably performed in the range of 50 ° C. to 120 ° C. in terms of a good reaction yield.

  Compound (5) can be obtained by performing a usual treatment after completion of “Step 6”. If necessary, it may be purified by recrystallization, column chromatography or sublimation.

Although the manufacturing method of the thin film for organic electroluminescent elements which consists of a 1,3,5-triazine compound (1) of this invention is not specifically limited, The film-forming by a vacuum evaporation method is possible. Film formation by the vacuum evaporation method can be performed by using a general-purpose vacuum evaporation apparatus. The vacuum degree of the vacuum chamber when forming a film by the vacuum evaporation method is reached by a diffusion pump, a turbo molecular pump, a cryopump, etc. that are generally used in consideration of the manufacturing tact time and manufacturing cost of manufacturing the organic electroluminescence device. It is preferably about 1 × 10 ⁻² Pa to 1 × 10 ⁻⁵ Pa. The deposition rate is preferably 0.005 nm / sec to 1.0 nm / sec, although it depends on the thickness of the film to be formed. The 1,3,5-triazine compound (1) has a high solubility in chloroform, dichloromethane, 1,2-dichloroethane, chlorobenzene, toluene, ethyl acetate, tetrahydrofuran, or the like, and therefore, a spin coat method using a general-purpose apparatus. Film formation by an ink jet method, a cast method, a dip method, or the like is also possible.

JP 2006-62962 A J. et al. Tsuji, “Palladium Reagents and Catalysts, John Wiley & Sons, 2004. Journal of Organic Chemistry, 60, 7508-7510, 1995 Journal of Organic Chemistry, 65, 164-168, 2000

  The thin film comprising the 1,3,5-triazine compound (1) of the present invention has high surface smoothness, amorphousness, heat resistance, electron transport ability, hole blocking ability, redox resistance, water resistance, oxygen resistance, electron Since it has injection characteristics and the like, it is useful as a material for an organic electroluminescence device, and can be used as an electron transport material, a hole blocking material, a light emitting host material, and the like. Therefore, the thin film comprising the 1,3,5-triazine compound (1) of the present invention is expected to be used as a constituent component of the organic electroluminescence device.

  EXAMPLES Hereinafter, although an Example and a reference example are given and this invention is demonstrated further in detail, this invention is not limited to these.

^For the measurement of ¹ H-NMR spectrum, Bruker DPX250 and DPX500 spectrometers were used.

  The reagent used in the experiment was Sigma-Aldrich Co. , Ltd., Ltd. , Purchased from Tokyo Chemical Industry Co., Ltd., Wako Pure Chemical Industries, Ltd. and Kanto Chemical Co., Ltd. and purified as necessary.

  Tetrahydrofuran, which is a reaction solvent, was a non-stabilized and dehydrated product manufactured by Kanto Chemical Co., Inc.

  For column chromatography, spherical silica gel having a particle size of 63 μm to 210 μm manufactured by Kanto Chemical Co., Inc. was used.

Example 1
2- {4,4 ″ -bis (1,10-phenanthrolin-2-yl)-[1,1 ′; 3 ′, 1 ″]-terphenyl-5′-yl} -4,6-di-p Synthesis of tolyl-1,3,5-triazine

  Under an argon stream, 2- (3,5-dibromophenyl) -4,6-di-p-tolyl-1,3,5-triazine 248 mg (0.500 mmol), 2- [4- (4,4,5 , 5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] -1,10-phenanthroline 420 mg (1.10 mmol), cesium carbonate 358 mg (1.10 mmol), palladium acetate 2.3 mg (0. 01 mmol) and 5.2 mg (0.02 mmol) of triphenylphosphine were suspended in 30 mL of tetrahydrofuran and refluxed for 14 hours. After cooling to room temperature, low-boiling components were removed under reduced pressure, methanol was added, and the precipitated solid was filtered off. The obtained crude product was purified by silica gel chromatography (developing solvent: methanol: chloroform = 1: 40) to obtain the desired 2- {4,4 ″ -bis (1,10-phenanthrolin-2-yl)-[1. , 1 ′; 3 ′, 1 ″]-terphenyl-5′-yl} -4,6-di-p-tolyl-1,3,5-triazine (402 mg, 95% yield) Obtained.

¹ H-NMR (CDCl ₃ ): δ 2.51 (s, 6H), 7.42 (d, J = 8.2 Hz, 4H), 7.68 (dd, J = 8.1, 4.4 Hz, 2H) ), 7.84 (d, J = 5.5 Hz, 4H), 8.05 (d, J = 8.4 Hz, 4H), 8.23 (m, 1H), 8.24 (d, J = 8) .4 Hz, 2H), 8.29 (dd, J = 8.1, 1.7 Hz, 2H), 8.37 (d, J = 8.4 Hz, 2H), 8.58 (d, J = 8. 4 Hz, 4H), 8.73 (d, J = 8.2 Hz, 4H), 9.11 (d, J = 1.7 Hz, 2H), 9.29 (dd, J = 4.4, 1.7 Hz) , 2H).
Example 2
2,4-bis (biphenyl-3-yl) -6- {3,5-bis [4- (1,10-phenanthrolin-2-yl) naphthalen-1-yl] phenyl} -1,3,5- Synthesis of triazine

  Under an argon stream, 2,4-di-m-biphenyl-6- (3,5-dibromophenyl) -1,3,5-triazine 172 mg (0.278 mmol), 2- [1- (4,4,5 , 5-tetramethyl-1,3,2-dioxaborolan-2-yl) naphthalen-4-yl] -1,10-phenanthroline 300 mg (0.694 mmol), cesium carbonate 453 mg (1.39 mmol), palladium acetate (II ) 3.1 mg (0.014 mmol) and 2-dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl (13.3 mg, 0.028 mmol) were suspended in tetrahydrofuran (30 mL) and refluxed for 14 hours. After cooling to room temperature, low-boiling components were removed under reduced pressure, methanol was added, and the precipitated solid was filtered off. The obtained crude product was purified by silica gel chromatography (developing solvent: methanol: chloroform = 1: 50 to 1:40) and then recrystallized from chloroform-methanol to obtain the desired 2,4-bis (biphenyl-3-). Yl) -6- {3,5-bis [4- (1,10-phenanthrolin-2-yl) naphthalen-1-yl] phenyl} -1,3,5-triazine (yield 11 mg, yield) 4%).

¹ H-NMR (CDCl ₃ ): δ 7.33 (brt, J = 7.2 Hz, 2H), 7.40-7.53 (m, 8H), 7.57-7.68 (m, 8H), 7.76-7.78 (m, 2H), 7.77 (brd, J = 8.2 Hz, 2H), 7.84 (d, J = 6.8 Hz, 4H), 7.92-7.99 (M, 5H), 8.15-8.26 (m, 6H), 8.36 (d, J = 8.3 Hz, 2H), 8.73 (brd, J = 7.7 Hz, 2H), 8 .96 (brs, 2H), 9.00 (d, J = 1.6 Hz, 2H), 9.17 (dd, J = 4.4, 1.7 Hz, 2H).
Example 3
2- {4,4 ″ -bis (benzo [h] quinolin-2-yl)-[1,1 ′; 3 ′, 1 ″]-terphenyl-5′-yl} -4,6-di (naphthalene) Synthesis of 2-yl) -1,3,5-triazine

  Under an argon stream, 334 mg (1.00 mmol) of 2- (4-bromophenyl) benzo [h] quinoline was dissolved in 20 mL of tetrahydrofuran, and 0.68 mL of a hexane solution containing 1.10 mmol of butyllithium was added dropwise at −78 ° C. . The solution was stirred at −78 ° C. for 15 minutes, 278 mg (1.10 mmol) of dichloro (tetramethylethylenediamine) zinc (II) was added, stirred for 30 minutes, and then warmed to room temperature. 2- (3,5-dibromophenyl ) -4,6-di (naphthalen-2-yl) -1,3,5-triazine 189 mg (0.333 mmol), tetrakis (triphenylphosphine) palladium (0) 15.4 mg (0.013 mmol) were added, Refluxed for 13.5 hours. After cooling to room temperature, low-boiling components were removed under reduced pressure, methanol was added, and the precipitated solid was filtered off. The obtained crude product was purified by silica gel chromatography (developing solvent: chloroform), and 2- {4,4 ″ -bis (benzo [h] quinolin-2-yl)-[1,1 ′; 3 ′, 1 ”] -Terphenyl-5′-yl} -4,6-di (naphthalen-2-yl) -1,3,5-triazine was obtained as a white solid (yield 231 mg, yield 76%).

¹ H-NMR (CDCl ₃ ): δ 7.61-7.64 (m, 4H), 7.76 (d, J = 8.9 Hz, 2H), 7.71-7.87 (m, 4H), 7.85 (d, J = 8.9 Hz, 2H), 7.94-7.97 (m, 4H), 8.10 (d, J = 8.3 Hz, 4H), 8.14-8.22 (M, 4H), 8.16 (d, J = 8.4 Hz, 2H), 8.29 (brs, 1H), 8.31 (d, J = 8.4 Hz, 2H), 8.60 (d , J = 8.3 Hz, 4H), 8.94 (dd, J = 8.6, 1.7 Hz, 2H), 9.21 (d, J = 1.7 Hz, 2H), 9.45 (brs, 2H), 9.59 (brd, J = 7.6 Hz, 2H).
Example 4
2,4-bis (biphenyl-3-yl) -6- {3,5-bis [6- (benzo [h] quinolin-2-yl) pyridin-2-yl] phenyl} -1,3,5- Synthesis of triazine

  2,4-bis (biphenyl-3-yl) -6- [3,5-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl under an argon stream ] -1,3,5-triazine 266 mg (0.373 mmol), 2- (6-bromopyridin-2-yl) benzo [h] quinoline 250 mg (0.746 mmol), cesium carbonate 486 mg (1.49 mmol), dichloro Bistriphenylphosphine palladium (II) 13.1 mg (0.019 mmol) was suspended in tetrahydrofuran 20 mL and refluxed for 18 hours. After cooling to room temperature, low-boiling components were removed under reduced pressure, methanol was added, and the precipitated solid was filtered off. The obtained crude product was purified by silica gel chromatography (developing solvent: chloroform) and recrystallized from chloroform to obtain 2,4-bis (biphenyl-3-yl) -6- {3,5-bis [6- (benzo A yellow solid (yield 155 mg, 43% yield) of [h] quinolin-2-yl) pyridin-2-yl] phenyl} -1,3,5-triazine was obtained.

¹ H-NMR (CDCl ₃ ): δ 7.34 (m, 2H), 7.47 (t, J = 7.7 Hz, 4H), 7.75-7.79 (m, 6H), 7.84 ( d, J = 7.0 Hz, 2H), 7.85-7.87 (m, 4H), 7.90 (d, J = 8.7 Hz, 2H), 7.95 (brd, J = 7.7 Hz). , 2H), 8.00 (d, J = 7.5 Hz, 2H), 8.13 (d, J = 8.3 Hz, 2H), 8.18 (t, J = 7.7 Hz, 2H), 8 .21 (dd, J = 7.7, 1.0 Hz, 2H), 8.95 (brd, J = 7.7 Hz, 2H), 9.04 (dd, J = 7.5, 1.0 Hz, 2H) ), 9.12 (d, J = 8.3 Hz, 2H), 9.21 (t, J = 1.7 Hz, 2H), 9.38 (t, J = 1.7 Hz, 1H), 9.61 (D, J = 8.1H , 2H), 9.83 (d, J = 1.7Hz, 2H).
Reference example 1
2,4-bis (biphenyl-3-yl) -6- [3,5-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl] -1, Synthesis of 3,5-triazine

  Under an argon stream, 310 mg (0.500 mmol) of 2,4-di-m-biphenyl-6- (3,5-dibromophenyl) -1,3,5-triazine, 305 mg (1.20 mmol) of bispinacolato diboron , 236 mg (2.40 mmol) of potassium acetate and 17.5 mg (0.025 mmol) of dichlorobistriphenylphosphine palladium (II) were suspended in 20 mL of tetrahydrofuran and refluxed for 18 hours. After cooling to room temperature, low-boiling components were removed under reduced pressure, methanol was added, and the precipitated solid was filtered off. The obtained crude product was purified by silica gel chromatography (developing solvent chloroform), and 2,4-bis (biphenyl-3-yl) -6- [3,5-bis (4,4,5,5-tetra). A white solid (yield 305 mg, yield 85%) of methyl-1,3,2-dioxaborolan-2-yl) phenyl] -1,3,5-triazine was obtained.

¹ H-NMR (CDCl ₃ ): δ 1.34 (s, 24H), 7.35 (brt, J = 7.3 Hz, 2H), 7.45 (brt, J = 7.3 Hz, 4H), 7. 61 (t, J = 7.7 Hz, 2H), 7.73 (brd, J = 7.3 Hz, 4H), 7.80 (brdddd, J = 7.7, 1.6, 1.6 Hz, 2H) 8.45 (brs, 1H), 8.73 (brdddd, J = 7.7, 1.6, 1.6 Hz, 2H), 9.02 (brt, J = 1.6 Hz, 2H), 9. 22 (d, J = 1.2 Hz, 2H).
[Embodiment]
Fabrication and performance evaluation of organic electroluminescence device having 1,3,5-triazine as a constituent component A glass substrate with an ITO transparent electrode in which a 2 mm-wide indium-tin oxide (ITO) film is patterned in a stripe shape is used as a substrate. Use. After this substrate is cleaned with isopropyl alcohol, surface treatment is performed by ozone ultraviolet cleaning. Each layer is vacuum-deposited on the cleaned substrate by a vacuum deposition method to produce an organic electroluminescent device having a light-emitting area of 4 mm ² as shown in a sectional view in FIG. First, the said glass substrate is introduce | transduced in a vacuum evaporation tank, and it pressure-reduces to 1.0 * 10 <^-4> Pa. Thereafter, a hole injection layer 2, a hole transport layer 3, a light emitting layer 4 and an electron transport layer 5 are sequentially formed as an organic compound layer on the glass substrate shown by 1 in FIG. 1, and then a cathode layer 6 is formed. Film. As the hole injection layer 2, sublimated and purified phthalocyanine copper (II) is vacuum-deposited with a film thickness of 25 nm. As the hole transport layer 3, N, N′-di (naphthylene-1-yl) -N, N′-diphenylbenzidine (NPD) is vacuum-deposited with a film thickness of 45 nm. The light-emitting layer 4 includes 4,4′-bis (2,2-diphenyl-ethen-1-yl) diphenyl (DPVBi) and 4,4′-bis [4- (di-p-tolylamino) styryl] biphenyl ( DPAVBi) is vacuum-deposited at a ratio of 99: 1 mass% with a film thickness of 40 nm. As the electron transport layer 5, the 1,3,5-triazine compound of the present invention or the existing material tris (8-quinolinolato) aluminum (III) (Alq) is vacuum-deposited to a thickness of 20 nm. Each organic material is formed into a film by a resistance heating method, and the heated compound is vacuum-deposited at a film formation rate of 0.3 nm / second to 0.5 nm / second. Finally, a metal mask is disposed so as to be orthogonal to the ITO stripe, and the cathode layer 6 is formed. The cathode layer 6 has a two-layer structure in which lithium fluoride and aluminum are vacuum-deposited with a thickness of 0.5 nm and 100 nm, respectively. Each film thickness is measured with a stylus type film thickness meter (DEKTAK). Further, this element is sealed in a nitrogen atmosphere glove box having an oxygen and moisture concentration of 1 ppm or less. For sealing, a glass sealing cap and the above-mentioned film-forming substrate epoxy type ultraviolet curable resin (manufactured by Nagase ChemteX Corporation) are used.

A direct current is applied to the produced organic electroluminescent element, and the light emission characteristics are evaluated using a luminance meter of LUMINANCE METER (BM-9) manufactured by TOPCON. As light emission characteristics, voltage (V), luminance (cd / m ² ), current efficiency (cd / A), and power efficiency (lm / W) when a current density of 20 mA / cm ² is passed are measured, and when continuously lit Measure the luminance half-life of.

  If the compound of the present invention is used, lower power consumption and longer life are expected compared to existing materials.

It is sectional drawing of the organic electroluminescent element produced by embodiment (element evaluation).

Explanation of symbols

1. 1. Glass substrate with ITO transparent electrode 2. hole injection layer Hole transport layer 4. 4. Light emitting layer Electron transport layer 6. Cathode layer

Claims (9)

General formula (1)

[Wherein, R ¹ , R ² and R ³ each independently represents a hydrogen atom or a methyl group. V and W represent a carbon atom or a nitrogen atom. Ar represents an optionally substituted aromatic hydrocarbon group. ]
The 1,3,5-triazine compound shown by these. The 1,3,5-triazine compound according to claim ¹ , wherein R ¹ , R ² and R ³ are hydrogen atoms. The 1,3,5-triazine compound according to claim 1 or 2, wherein V is a carbon atom. The 1,3,5-triazine compound according to any one of claims 1 to 3, wherein Ar is a phenyl group which may be substituted or a naphthyl group which may be substituted. General formula (2)

[In formula, V and W represent a carbon atom or a nitrogen atom. M represents ZnR ⁴ , MgR ⁵ , Sn (R ⁶ ) ₃ , B (OR ⁷ ) ₂ . However, R < ⁴ > and R < ⁵ > respectively independently represents a chlorine atom, a bromine atom, or an iodine atom, R < ⁶ > represents a C1-C4 alkyl group or a phenyl group, R < ⁷ > is a hydrogen atom, C1-C1 4 represents an alkyl group or a phenyl group, and R ⁶ and R ⁷ may be the same or different from each other. Two R ⁷ can also form a ring integrally with a boron atom bonded through an oxygen atom. ]
And a compound of the general formula (3)

[Wherein, R ¹ , R ² and R ³ each independently represents a hydrogen atom or a methyl group. Ar represents an optionally substituted aromatic hydrocarbon group. Y ¹ represents a chlorine atom, a bromine atom, an iodine atom or a trifluoromethanesulfoxy group. ]
Wherein the compound represented by the general formula (1) is subjected to a coupling reaction in the presence or absence of a base in the presence of a palladium catalyst.

[Wherein, R ¹ , R ² , R ³ , V, W and Ar are the same as defined above. ]
The manufacturing method of the 1,3,5-triazine compound shown by these. General formula (4)

[In formula, V and W represent a carbon atom or a nitrogen atom. Y ² represents a chlorine atom, a bromine atom, an iodine atom or a trifluoromethanesulfoxy group. ]
And a compound of the general formula (5)

[Wherein, R ¹ , R ² and R ³ each independently represents a hydrogen atom or a methyl group. Ar represents an optionally substituted aromatic hydrocarbon group. R ⁷ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group, and R ⁷ may be the same or different from each other. Two R ⁷ can also form a ring integrally with a boron atom bonded through an oxygen atom. ]
The compound represented by the general formula (1) is subjected to a coupling reaction in the presence of a base and a palladium catalyst.

[Wherein, R ¹ , R ² , R ³ , V, W and Ar are the same as defined above. ]
The manufacturing method of the 1,3,5-triazine compound shown by these. The method for producing a 1,3,5-triazine compound according to claim 5 or 6, wherein the palladium catalyst is a palladium complex having a tertiary phosphine as a ligand. The tertiary phosphine is triphenylphosphine, 1,1'-bis (diphenylphosphino) ferrocene, 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl. 8. A process for producing a 1,3,5-triazine compound according to 7. General formula (1)

[Wherein, R ¹ , R ² and R ³ each independently represents a hydrogen atom or a methyl group. V and W represent a carbon atom or a nitrogen atom. Ar represents an optionally substituted aromatic hydrocarbon group. ]
An organic electroluminescent device comprising a 1,3,5-triazine compound represented by the formula:

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