CN1919842A - Oxdiazole derivative and application thereof in electroluminescent material - Google Patents
Oxdiazole derivative and application thereof in electroluminescent material Download PDFInfo
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- CN1919842A CN1919842A CN 200610116087 CN200610116087A CN1919842A CN 1919842 A CN1919842 A CN 1919842A CN 200610116087 CN200610116087 CN 200610116087 CN 200610116087 A CN200610116087 A CN 200610116087A CN 1919842 A CN1919842 A CN 1919842A
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Abstract
The invention discloses an oxdiazole compound and complex of its ligand and application, which is characterized by the following: the complex possesses the structure in the formula (2), wherein R1 is H, C1-C6 alkyl, C1-C6 alkoxy, halogen, hydroxyl group, C6-C12 aromatic ring group or C6-C12 aromatic heterocyclic radical with N; R2 is H, C1-C6 alkyl, C1-C6 halogenated alkyl groups, C6-C12 aromatic ring group or substituted C6-C12 aromatic ring group by C1-C6 alkyl, C1-C6 alkoxy, halogen, hydroxyl group or carbazolyl; R3 and R4 is one of H, C1-C18 alkyl, C5-C18 aromatic ring group or C5-C18 aromatic heterocyclic radical; R5 is H, C1-C18 alkyl, C5-C18 aromatic ring group or C5-C18 aromatic heterocyclic radical; n=1-4; m is 2 or 3; p is 0 or 1; the heteroatom in the aromatic heterocyclic radical is N, O or and S.
Description
Technical field
The present invention relates to Yi Zhong oxadiazole derivative and uses thereof, specifically, relate to Yi Zhong oxadiazole compounds, reaching with described compound is the purposes of the title complex and the title complex of part.
Background technology
Organic electroluminescence device (OLEDs) but have advantages such as low in energy consumption, flexible, that response speed is fast, the wide big area in visual angle shows, luminous color is complete, and can make luminescent device cheaply with existing multiple standards, technical compatibility, thereby realizing having demonstrated great vitality aspect the coloured plate demonstration, and caused the extensive attention of international each major company.
Luminous organic material is an integral part crucial in the organic electroluminescence device, selects different organic materialss for use, just can obtain various color.Luminescent layer can be divided into two classes basically from luminescence mechanism, i.e. fluorescence luminescent material and phosphorescent light-emitting materials.And phosphorescent light-emitting materials adopts phosphorescent coloring octaethyl porphines platinum (PtOEP) that the material of organic luminous layer is mixed since people such as M.A.Baldo in 1998, has obtained developing widely and using since preparing the OLED of high-luminous-efficiency and internal quantum efficiency.Wherein complex of iridium is because preparation is simple, easily purifying and can obtain that full spectrographic is luminous more and more to be paid attention to by ligand modified.
The oxadiazole compounds is by one of the electric transmission body of widespread use and luminescent material [as 2,5-two (1-naphthyl)-1,3,4-oxadiazole (BND) and 2-xenyl-5-(4-tert-butyl-phenyl)-1,3,4-oxadiazole (PBD)].Because their electron deficiency, high photoluminescence quantum efficiencies, thermostability and chemical stability preferably, they are direct evaporation both, also can be dispersed in spin-coating film in the inert macromolecular material, also can directly be dispersed in synchronous processing in the parent of luminous high polymer, be widely used in the organic EL device.Therefore, design and synthesize extremely this area researchist's the concern of the better novel oxadiazole derivative of performance.
Summary of the invention
One of the object of the invention is, a kind of novel oxadiazole compounds is provided;
Two of the object of the invention is, provides more than one to state the title complex that the novel oxadiazole compounds is a part;
Three of the object of the invention is, discloses the purposes that more than one state title complex.
Suo of the present invention is Shuoed De oxadiazole compounds, and it has structure shown in the formula (1):
In the formula (1), R
1Be H, C
1～C
6Alkyl, C
1～C
6Alkoxyl group, halogen, hydroxyl, C
6～C
12Aromatic ring yl or contain the C of N
6～C
12Aromatic heterocyclic; R
2Be H, C
1～C
6Alkyl, C
1～C
6Haloalkyl, C
6～C
12Aromatic ring yl or by C
1～C
6Alkyl, C
1～C
6The C that alkoxyl group, halogen, hydroxyl or carbazyl [its structure is suc as formula shown in (1a)] replace
6～C
12Aromatic ring yl; N=1～4.
In the present invention:
Preferred R
1Be C
1～C
3Alkoxyl group, hydroxyl, F, Br, C
6～C
12Aromatic ring yl or contain the C of N
6～C
12Aromatic heterocyclic, preferred R
1Be methoxyl group, F, phenyl or carbazyl;
Preferred R
2Be C
1～C
3Haloalkyl, C
6～C
12Aromatic ring yl or by C
1～C
3The C that alkoxyl group, halogen or carbazyl replace
6～C
12Aromatic ring yl, preferred R
2For naphthyl or by C
1～C
3The phenyl that alkoxyl group, F, Br or carbazyl replace;
Preferred n=1～3.
The said title complex of the present invention, it has structure shown in the formula (2):
In the formula (2), R
1, R
2And the definition of n as hereinbefore; R
3, R
4Be selected from C respectively
1～C
18Alkyl, C
5～C
18Aromatic ring yl or C
5～C
18A kind of in the aromatic heterocyclic; R
5Be H, C
1～C
18Alkyl, C
5～C
18Aromatic ring yl or C
5～C
18Aromatic heterocyclic; M is 2 or 3; P is 0 or 1;
Wherein: the contained heteroatoms of described aromatic heterocyclic is that N, O are or/and S.
In the present invention:
Preferred R
3, R
4Be selected from C respectively
1～C
6Alkyl, C
5～C
10Aromatic ring yl or C
5～C
10A kind of in the aromatic heterocyclic, preferred R
3, R
4Be selected from C respectively
1～C
3Alkyl, C
5～C
6Aromatic ring yl or C
5～C
6A kind of in the aromatic heterocyclic;
Preferred R
5Be H, C
1～C
6Alkyl C
5～C
10Aromatic ring yl or C
5～C
10Aromatic heterocyclic, preferred R
5Be H, C
1～C
3Alkyl C
5～C
6Aromatic ring yl or C
5～C
6Aromatic heterocyclic.
It is as follows that synthetic Suo of the present invention is Shuoed the synthetic route of De oxadiazole compounds [compound shown in the formula (1)]:
R in the synthetic route
1, R
2And the definition of n is described identical with preamble.
● at first in dehydrated alcohol, refluxed 12 hours compound shown in the acquisition formula (5) by compound shown in the formula (3) and hydrazine hydrate; Reflux in thionyl chloride by compound shown in the formula (5) and carboxylic acid shown in the formula (6) then and became compound (one of target compound of the present invention) shown in the ring acquisition formula (1) in 24 hours;
Or
● at first by compound shown in the formula (4) and hydrazine hydrate in methylene dichloride in stirring at room 12 hours, compound shown in the acquisition formula (5); Reflux in thionyl chloride by compound shown in the formula (5) and carboxylic acid shown in the formula (6) then and became compound (one of target compound of the present invention) shown in the ring acquisition formula (1) in 24 hours.
The key step of the preparation said title complex of the present invention [compound shown in the formula (2)] is as follows:
● compound (part) shown in 2～3 normal formulas (1), ethylene glycol monomethyl ether and six sodium iridichlorides or three hydration iridous chlorides are placed reactor, reflux 36 hours, adding compound shown in 2 normal yellow soda ash and the 5 normal formulas (7) after the cooling again refluxed 36 hours, pour in the water, through column chromatography, obtain compound shown in the formula (2) (target compound two) behind the solid drying that suction filtration obtains;
In the formula (7), R
3, R
4And R
5Definition described identical with preamble.
Or
● the 24h that in glycerine, refluxes of compound (part) shown in praseodynium iridium and 2～3 normal formulas (1), add the hydrochloric acid of 2N, extraction obtains compound shown in (2) and p=0 (target compound three) through column chromatography again.
The title complex that the present invention designs and synthesizes [compound shown in the formula (2)] has higher thermostability, and has higher phosphorescence luminous efficiency, can be used as electron transport material, phosphorescent light-emitting materials is applied in the electroluminescent device.
Description of drawings
Fig. 1 is the ultraviolet-visible absorption figure that compound two { 2,5-two (2-fluorophenyl)-1,3,4-oxadiazole } (methyl ethyl diketone) closes iridium (III).
Fig. 2 is that compound two { 2,5-two (2-fluorophenyl)-1,3,4-oxadiazole } (methyl ethyl diketone) closes the photoluminescence figure of iridium (III) solution.
Fig. 3 is that compound two { 2,5-two (2-fluorophenyl)-1,3,4-oxadiazole } (methyl ethyl diketone) closes the room temperature phosphorimetry life-span decay pattern of iridium (III) solution.
Embodiment
The present invention is further elaborated below by embodiment, and its purpose is better to understand content of the present invention.Therefore, the cited case should not be considered as limiting the scope of the invention.
Embodiment 1
2,5-two (4-p-methoxy-phenyl)-1,3, the preparation of 4-oxadiazole:
In flask, add the 10.0g ethyl anisate, the 50ml dehydrated alcohol, the 15ml hydrazine hydrate, reflux 12h, steaming is poured into while hot except that ethanol and is obtained white solid in the water then, once obtain pure product to methoxybenzoyl hydrazine 8.0g with the dehydrated alcohol recrystallization, (m.p.139-141 ℃).Productive rate 80%.In flask, add 5.0g to the methoxybenzoyl hydrazine, 6.0g anisic acid, 50ml thionyl chloride, backflow 24h, cooling is slowly poured in the frozen water, after stirring is spent the night, suction filtration obtains solid, obtains target compound 3.6g (m.p.162-164 ℃) behind the ethyl alcohol recrystallization, productive rate 41.9%.
1H-NMR(CDCl
3)δ：8.07(d，4H)，7.03(d，4H)，3.90(s，6H)。
Embodiment 2
2,5-two (2-fluorophenyl)-1,3, the preparation of 4-oxadiazole:
In flask, add 15.4g o-fluorobenzoic acid methyl esters, the 50ml dehydrated alcohol, the 15ml hydrazine hydrate, reflux 12h, steaming is poured into while hot except that ethanol and is obtained white solid in the water then, once obtain the adjacent fluorobenzoyl hydrazine of pure product 12.3g (m.p.72-74 ℃), productive rate 79.9% with the dehydrated alcohol recrystallization.In flask, add the adjacent fluorobenzoyl hydrazine of 5.0g, the 6.0g o-fluorobenzoic acid, the 50ml thionyl chloride, backflow 24h, cooling is slowly poured in the frozen water, after stirring was spent the night, suction filtration obtained solid, obtained target compound behind the ethyl alcohol recrystallization, 2,5-two (2-fluorophenyl)-1,3, the 4-oxadiazole, (4.3g m.p.162-164 ℃), productive rate 51.3%.
1H-NMR(CDCl
3)δ：8.17(t，2H)，7.57(m，2H)，7.34(m，2H)，7.28(m，2H)。
2-(2, the 6-difluorophenyl)-5-(4-p-methoxy-phenyl)-1,3,4-oxadiazole synthetic:
In flask, add the 10.0g methyl p-methoxybenzoate, the 50ml dehydrated alcohol, the 15ml hydrazine hydrate, reflux 12h, steaming is poured into while hot except that ethanol and is obtained white solid in the water then, once obtains pure product to methoxybenzoyl hydrazine 8.0g with the dehydrated alcohol recrystallization.Productive rate 79.9% (m.p.139-141 ℃).In flask, add 5.0g to the methoxybenzoyl hydrazine, 6.0g 2, the 6-difluoro-benzoic acid, 50ml thionyl chloride, backflow 24h, cooling is slowly poured in the frozen water, and after stirring was spent the night, suction filtration obtained solid, obtain target compound behind the ethyl alcohol recrystallization, 2-(2, the 6-difluorophenyl)-5-(4-p-methoxy-phenyl)-1,3, the 4-oxadiazole, 2.3g (m.p.192-194 ℃), productive rate 26.5%.
1H-NMR(CDCl
3)δ：8.07(d，2H)，7.77(d，2H)，7.43(t，1H)，7.03(d，2H)，3.90(s，3H)。
Embodiment 4
2,5-two (betanaphthyl)-1,3,4-oxadiazole synthetic:
In flask, add 10.0g β-2-methyl naphthoate, the 50ml dehydrated alcohol, the 15ml hydrazine hydrate, reflux 12h, steaming is poured into while hot except that ethanol and is obtained white solid in the water then, once obtain pure product β-naphthoyl hydrazine 7.2g (m.p.147-149 ℃), productive rate 73.1% with the dehydrated alcohol recrystallization.β-naphthoyl hydrazine 5.0g, β-naphthoic acid 10.0g joins in the thionyl chloride of 25ml, mixture backflow 10h, pour in the water, obtain 2 behind the solid ethyl alcohol recrystallization that obtains, 5-two (betanaphthyl)-1,3, the 4-oxadiazole, 3.79g (m.p.198-202 ℃), productive rate 43.5%.
1H-NMR(CDCl
3)δ：8.00(d，4H)，7.87(m，4H)，7.60(d，4H)，6.79(s，2H)。
Embodiment 5
2,5-two (4-N-carbazyl phenyl)-1,3,4-oxadiazole synthetic
In flask, add 10.0g 4-N-carbazyl Benzoyl chloride, the 50ml methylene dichloride; slowly splash into the 1.5ml hydrazine hydrate, stirring at room 12h pours into then and obtains white solid in the water; once obtain pure product 4-N-carbazyl benzoyl hydrazine, 6.1g with the dehydrated alcohol recrystallization.In flask, add 5.0g 4-N-carbazyl benzoyl hydrazine, 5.0g 4-N-carbazyl phenylformic acid; the 20ml phosphorus oxychloride, backflow 24h, cooling is slowly poured in the frozen water; after stirring was spent the night, suction filtration obtained solid, obtained target compound behind the toluene recrystallization; 2; 5-two (4-N-carbazyl phenyl)-1,3, the 4-oxadiazole; (2.1g m.p.210-215 ℃), overall productive rate 25.3%.
1H-NMR(CDCl
3)δ：8.27(d，4H)，8.07(d，4H)，7.67(t，8H)，7.03(d，4H)，7.90(m，4H)。
Embodiment 6
Two { 2,5-two (2-fluorophenyl)-1,3,4-oxadiazole } (methyl ethyl diketones) close the synthetic of iridium (III)
With 2 of 55mg, 5-two (2-fluorophenyl)-1,3, six sodium iridichlorides of 4-oxadiazole and the 50mg 36h that refluxes in the 20ml ethylene glycol monomethyl ether adds the methyl ethyl diketone of 5ml, the yellow soda ash of 100mg then, mixture backflow 36h, pour in the water, the solid that obtains obtains target compound, two { 2 through column chromatography, 5-two (2-fluorophenyl)-1,3,4-oxadiazole } (methyl ethyl diketone) close iridium (III) 15mg, and overall productive rate is 17.4%.
1H-NMR(CDCl
3)δ：8.26(d×d，2H)，7.62(d×d，2H)，7.37(t，2H)，7.32(t，2H)，6.87(d×d，2H)，6.62(t，2H)，6.45(d，2H)，5.31(s，1H)，1.93(s，6H)。
Embodiment 7
The synthetic of iridium (III) closed in three { 2,5-two (4-p-methoxy-phenyl)-1,3,4-oxadiazole }
With 2 of 60mg, 5-two (4-p-methoxy-phenyl)-1,3, the praseodynium iridium of 4-oxadiazole and the 50mg 24h that in 20ml glycerine, refluxes, add the hydrochloric acid of 2N then, use dichloromethane extraction, revolve the oily matter that obtains after the steaming and obtain target compound through column chromatography, three { 2,5-two (4-p-methoxy-phenyl)-1,3,4-oxadiazole } close iridium (III), 16mg, overall productive rate is 21.7%.
1H-NMR(CDCl
3)δ：8.13(d，6H)，7.51(d，3H)，7.05(d，6H)，6.48(d×d，3H)，6.19(d，3H)，4.28(s，9H)，4.21(s，9H)。
Embodiment 8
Two { 2,5-two (betanaphthyl)-1,3,4-oxadiazole } (diphenylpropane-1,3-dione(DPPO)s) close the synthetic of iridium (III)
With 2 of 60mg, 5-two (betanaphthyl)-1,3, the iridous chloride of 4-oxadiazole and the 50mg 24h that refluxes in the 20ml ethylene glycol monomethyl ether adds the 200mg diphenylpropane-1,3-dione(DPPO), 50mg yellow soda ash then, backflow 36h, pour in the water, the solid that obtains obtains target compound, two { 2 through column chromatography, 5-two (betanaphthyl)-1,3,4-oxadiazole } (diphenylpropane-1,3-dione(DPPO)) close iridium (III) 17mg, and overall productive rate is 17.2%.
1H-NMR(CDCl
3)δ：8.13(d，4H)，7.81(m，4H)，7.76(s，2H)，7.51(d，2H)，7.13(d，4H)，7.05(d，4H)，6.48(d×d，2H)，6.19(d，2H)，5.28(s，1H)。
Embodiment 9
Two { 2,5-two (4-N-carbazyl phenyl)-1,3,4-oxadiazole } (methyl ethyl diketones) close the synthetic of iridium (III)
With 2 of 55mg, 5-two (4-N-carbazyl phenyl)-1,3, six sodium iridichlorides of 4-oxadiazole and the 50mg 36h that refluxes in the 20ml ethylene glycol monomethyl ether adds the methyl ethyl diketone of 5ml, the yellow soda ash of 100mg then, mixture backflow 36h, pour in the water, the solid that obtains obtains target compound, two { 2 through column chromatography, 5-two (4-N-carbazyl phenyl)-1,3,4-oxadiazole } (methyl ethyl diketone) close iridium (III) 15mg, and overall productive rate is 18%.
1H-NMR(CDCl
3)δ：8.36(d，4H)，7.45(d，4H)，7.32(m，16H)，7.23(m，16H)，6.77(d，2H)，6.48(s，2H)，6.45(d，2H)，5.31(s，1H)，3.91(s，6H)。
Embodiment 10～16
Adopt with embodiment 1～9 similar method and can prepare following compounds (specifically seeing Table 1).
Table 1
Continuous table 1
Claims (12)
1, Yi Zhong oxadiazole compounds, it has structure shown in the formula (1):
In the formula (1), R
1Be H, C
1～C
6Alkyl, C
1～C
6Alkoxyl group, halogen, hydroxyl, C
6～C
12Aromatic ring yl or contain the C of N
6～C
12Aromatic heterocyclic; R
2Be H, C
1～C
6Alkyl, C
1～C
6Haloalkyl, C
6～C
12Aromatic ring yl or by C
1～C
6Alkyl, C
1～C
6The C that alkoxyl group, halogen, hydroxyl or carbazyl replace
6～C
12Aromatic ring yl; N=1～4.
2, as claim 1 Suo Shu De oxadiazole compounds, it is characterized in that, wherein R
1Be C
1～C
3Alkoxyl group, hydroxyl, F, Br, C
6～C
12Aromatic ring yl or contain the C of N
6～C
12Aromatic heterocyclic.
3, as claim 2 Suo Shu De oxadiazole compounds, it is characterized in that, wherein R
1Be methoxyl group, F, phenyl or carbazyl.
4, as claim 1 Suo Shu De oxadiazole compounds, it is characterized in that, wherein R
2Be C
1～C
3Haloalkyl, C
6～C
12Aromatic ring yl or by C
1～C
3The C that alkoxyl group, halogen or carbazyl replace
6～C
12Aromatic ring yl.
5, as claim 4 Suo Shu De oxadiazole compounds, it is characterized in that, wherein R
2For naphthyl or by C
1～C
3The phenyl that alkoxyl group, F, Br or carbazyl replace.
6, as any Suo Shu De oxadiazole compounds in the claim 1～5, it is characterized in that Suo Shu De oxadiazole compounds is 2,5-two (4-p-methoxy-phenyl)-1,3,4-oxadiazole, 2,5-two (2-fluorophenyl)-1,3,4-oxadiazole, 2-(2, the 6-difluorophenyl)-and 5-(4-p-methoxy-phenyl)-1,3,4-oxadiazole, 2,5-two (betanaphthyl)-1,3,4-oxadiazole or 2,5-two (4-N-carbazyl phenyl)-1,3, the 4-oxadiazole.
7, a kind of title complex is characterized in that, said title complex is a part with any Suo Shu De oxadiazole compounds in the claim 1～5, form with the coordination of metal iridium, its structure as the formula (2):
In the formula (2), R
3, R
4Be selected from C respectively
1～C
18Alkyl, C
5～C
18Aromatic ring yl or C
5～C
18A kind of in the aromatic heterocyclic; R
5Be H, C
1～C
18Alkyl, C
5～C
18Aromatic ring yl or C
5～C
18Aromatic heterocyclic; M is 2 or 3; P is 0 or 1; The contained heteroatoms of wherein said aromatic heterocyclic is that N, O are or/and S.
8, title complex as claimed in claim 7 is characterized in that, wherein R
3, R
4Be selected from C respectively
1～C
6Alkyl, C
5～C
10Aromatic ring yl or C
5～C
10A kind of in the aromatic heterocyclic; R
5Be H, C
1～C
6Alkyl, C
5～C
10Aromatic ring yl or C
5～C
10Aromatic heterocyclic.
9, title complex as claimed in claim 8 is characterized in that, wherein R
3, R
4Be selected from C respectively
1～C
3Alkyl, C
5～C
6Aromatic ring yl or C
5～C
6A kind of in the aromatic heterocyclic; R
5Be H, C
1～C
3Alkyl C
5～C
6Aromatic ring yl or C
5～C
6Aromatic heterocyclic.
10, title complex as claimed in claim 9 is characterized in that, described title complex is two { 2,5-two (2-fluorophenyl)-1,3,4-oxadiazole } (methyl ethyl diketone) close iridium (III), three { 2,5-two (4-p-methoxy-phenyl)-1,3,4-oxadiazole } close iridium (III), two { 2,5-two (betanaphthyl)-1,3,4-oxadiazole } (diphenylpropane-1,3-dione(DPPO)) close iridium (III) or 22,5-two (4-N-carbazyl phenyl)-1,3,4-oxadiazole } (methyl ethyl diketone) close iridium (III).
11, use in electron transport material as any described title complex in the claim 7～10.
12, use in electroluminescent phosphorescence luminescent material as any described title complex in the claim 7～10.
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