CN106554352B - Polycyclic aromatic hydrocarbon derivative containing naphthyridine group and application thereof - Google Patents
Polycyclic aromatic hydrocarbon derivative containing naphthyridine group and application thereof Download PDFInfo
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- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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Abstract
The invention relates to a polycyclic aromatic hydrocarbon derivative containing naphthyridine groups, which has a structure shown as a formula (1). The polycyclic aromatic hydrocarbon derivative containing naphthyridine groups is suitable for being used as an ETL material in an electroluminescent display. The use of the material can effectively reduce the working voltage of the organic electroluminescent device and improve the luminous efficiency of the organic electroluminescent device.
Description
Technical Field
The invention belongs to the field of organic electroluminescence, and particularly relates to a naphthyridine group-containing polycyclic aromatic hydrocarbon derivative, an intermediate thereof, a preparation method thereof and application thereof in an electron transport material.
Background
The electron transport material traditionally used in electroluminescent devices is Alq3However, Alq3Has a low electron mobility ratio (approximately at 10)-6cm2Vs). In order to improve the electron transport properties of electroluminescent devices, researchers have made a great deal of exploratory work.
LG chemistry in chinese patent specification CN 101003508A reports a series of pyrene derivatives as electron transporting and injecting materials in electroluminescent devices to improve the luminous efficiency of the devices. FFF-Blm4 (J.Am.chem.Soc.; (Communication); 2008; 130 (11); 3282-. Kodak in U.S. patents (publication nos. US 2006/0204784 and US 2007/0048545) mentioned a hybrid electron transport layer formed by doping one material with a low LUMO level material with another electron transport material with a low device operating voltage and other materials such as metallic materials. Devices based on such hybrid electron transport layers provide improved device efficiency, but increase the complexity of the device fabrication process, which is detrimental to OLED cost reduction. The stable and efficient electron transport material and/or electron injection material are/is developed, so that the device lighting and working voltage is reduced, the device efficiency is improved, the device service life is prolonged, and the method has important practical application value.
Disclosure of Invention
The invention aims to provide a novel polycyclic aromatic hydrocarbon derivative containing naphthyridine groups, which can be used in the field of organic electroluminescent display. In particular, the compounds can be used as electron transport materials in organic electroluminescent displays.
The use of the material can effectively reduce the working voltage of the organic electroluminescent device and improve the luminous efficiency of the organic electroluminescent device.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a polycyclic aromatic hydrocarbon derivative containing naphthyridine groups has a structure shown as a formula (1):
wherein: ar is selected from C10-C50A fused ring aromatic hydrocarbon group or a fused heterocyclic aromatic hydrocarbon group;
l may be a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclylene group.
R1And R2The same or different, are respectively and independently selected from H, aromatic hydrocarbon group, heterocyclic aromatic hydrocarbon group, condensed ring aromatic hydrocarbon group or condensed heterocyclic aromatic hydrocarbonA substituted or unsubstituted alkyl group, a cyano group.
The Ar is preferably a group represented by the formula (2) to the formula (7):
in the above formulae (2) to (7), Ar1And Ar2Same or different, each independently selected from H, C4-C30Aromatic ring group of (A), C4-C30Heteroaryl ring radical of (2), C4-C30With a condensed ring aromatic hydrocarbon group or C4-C30A fused heterocyclic aromatic hydrocarbon group of (a);
R4to R13The same or different, are respectively and independently selected from H, aromatic hydrocarbon group, heterocyclic aromatic hydrocarbon group, condensed ring aromatic hydrocarbon group, or condensed heterocyclic aromatic hydrocarbon group, substituted or unsubstituted alkyl and cyano.
Preferably, the naphthyridine group-containing fused ring aromatic hydrocarbon derivative has a structure represented by (8) to formula (11):
in the above formulae (7) to (11), Ar1And Ar2Same or different, each independently selected from H, C4-C30Aromatic ring group of (A), C4-C30Heteroaryl ring radical of (2), C4-C30With a condensed ring aromatic hydrocarbon group or C4-C30A fused heterocyclic aromatic hydrocarbon group of (a);
l is a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclylene group.
R4To R13The same or different, are respectively and independently selected from H, aromatic hydrocarbon group, heterocyclic aromatic hydrocarbon group, condensed ring aromatic hydrocarbon group, or condensed heterocyclic aromatic hydrocarbon group, substituted or unsubstituted alkyl and cyano.
The substituted or unsubstituted aromatic hydrocarbon group is phenyl, o-tolyl, p-tolyl or tert-butylphenyl; the substituted or unsubstituted heterocyclic aromatic hydrocarbon group is furan, benzofuran, dibenzofuran, thiophene, benzothiophene, dibenzothiophene, carbazole, pyridine, pyrazine, 2.4-methyl-1.3.5 triazine or 4.6 diphenylpyrimidine; the substituted or unsubstituted condensed ring aromatic hydrocarbon group is naphthyl, phenanthryl, anthryl, pyrenyl,
A fluorenyl, triphenylene, or 9, 9-dimethyl-2-fluorenyl group; the substituted or unsubstituted fused heterocyclic aromatic hydrocarbon group is quinoline, isoquinoline or quinazoline; the unsubstituted alkyl group is a methyl group, and the substituted alkyl group is a trifluoromethyl group. The substitution may be mono-or polysubstituted.
Preferably, the compound is of the formula (14) to (56):
the application of the polycyclic aromatic hydrocarbon derivative containing the naphthyridine group in an organic electroluminescent device.
The polycyclic aromatic hydrocarbon derivative containing the naphthyridine group can be used as an electron transport material.
An organic electroluminescent device comprises a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer which are sequentially formed on the substrate; the organic light-emitting functional layer comprises a hole transport layer, an organic light-emitting layer and an electron transport layer, and the electron transport material of the electron transport layer is the polycyclic aromatic hydrocarbon derivative containing the naphthyridine group.
Compared with the prior art, the polycyclic aromatic hydrocarbon derivative containing the naphthyridine group has the advantages that:
the condensed ring aromatic hydrocarbon derivative of the quinoxaline group belongs to a typical electron-deficient system, and has suitable HOMO and LUMO energy levels, so that the condensed ring aromatic hydrocarbon derivative has good electron accepting capacity. The condensed ring aromatic hydrocarbon system which is coplanar in a space structure has good electron transfer capability. Therefore, the benzacridine compound is an excellent electron transport material.
Experiments show that when the condensed ring aromatic hydrocarbon derivative of the quinoxaline group is used as an electron transmission material, compared with Bphen which is used as the electron transmission material, the driving voltage of a device is reduced, the working voltage of the device is effectively reduced, the lumen efficiency is improved, the power consumption of the device is reduced, and the condensed ring aromatic hydrocarbon derivative is an electron transmission material with good performance.
Drawings
FIG. 1 is a nuclear magnetic spectrum of a compound represented by the formula (15) ((1HNMR)；
FIG. 2 is a nuclear magnetic spectrum of a compound represented by the formula (25) ((1HNMR)；
FIG. 3 is a nuclear magnetic spectrum of a compound represented by the formula (33) ((1HNMR)；
FIG. 4 is a nuclear magnetic spectrum of a compound represented by the formula (38) ((1HNMR)；
FIG. 5 is a nuclear magnetic spectrum of a compound represented by the formula (47) (47)1HNMR)；
FIG. 6 is a nuclear magnetic spectrum of a compound represented by the formula (52) ((1HNMR)。
Detailed Description
The basic raw materials used in the present invention include, for example, various brominated derivatives of anthracene, brominated derivatives of diphenylbenzofluoranthene, brominated derivatives of triphenylene, and various brominated derivatives of triphenylene
Bromo derivative of (5)Or can be bought in various chemical raw material markets in China or can be synthesized by a common method in a laboratory. These bromides can be prepared into corresponding boric acid compounds by a common method. The 3, 7-dibromo-1, 5-naphthyridine can be conveniently purchased in chemical markets.
The invention provides a polycyclic aromatic hydrocarbon derivative containing naphthyridine groups, which has a structure shown as a formula (1):
wherein: ar is selected from C10-C50A fused ring aromatic hydrocarbon group or a fused heterocyclic aromatic hydrocarbon group;
l may be a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclylene group.
R1And R2The same or different, are respectively and independently selected from H, aromatic hydrocarbon group, heterocyclic aromatic hydrocarbon group, condensed ring aromatic hydrocarbon group, or condensed heterocyclic aromatic hydrocarbon group, substituted or unsubstituted alkyl and cyano.
The Ar is preferably a group represented by the formula (2) to the formula (7):
in the above formulae (2) to (7), Ar1And Ar2Same or different, each independently selected from H, C4-C30Aromatic ring group of (A), C4-C30Heteroaryl ring radical of (2), C4-C30With a condensed ring aromatic hydrocarbon group or C4-C30A fused heterocyclic aromatic hydrocarbon group of (a);
R4to R13The same or different, are respectively and independently selected from H, aromatic hydrocarbon group, heterocyclic aromatic hydrocarbon group, condensed ring aromatic hydrocarbon group, or condensed heterocyclic aromatic hydrocarbon group, substituted or unsubstituted alkyl and cyano.
Preferably, the naphthyridine group-containing fused ring aromatic hydrocarbon derivative has a structure represented by (8) to formula (11):
in the above formulae (7) to (11), Ar1And Ar2Same or different, each independently selected from H, C4-C30Aromatic ring group of (A), C4-C30Heteroaryl ring radical of (2), C4-C30With a condensed ring aromatic hydrocarbon group or C4-C30A fused heterocyclic aromatic hydrocarbon group of (a);
l is a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heterocyclylene group.
R4To R13The same or different, are respectively and independently selected from H, aromatic hydrocarbon group, heterocyclic aromatic hydrocarbon group, condensed ring aromatic hydrocarbon group, or condensed heterocyclic aromatic hydrocarbon group, substituted or unsubstituted alkyl and cyano.
The substituted or unsubstituted aromatic hydrocarbon group is phenyl, o-tolyl, p-tolyl or tert-butylphenyl; the substituted or unsubstituted heterocyclic aromatic hydrocarbon group is furan, benzofuran, dibenzofuran, thiophene, benzothiophene, dibenzothiophene, carbazole, pyridine, pyrazine, 2.4-methyl-1.3.5 triazine or 4.6 diphenylpyrimidine; the substituted or unsubstituted condensed ring aromatic hydrocarbon group is naphthyl, phenanthryl, anthryl, pyrenyl,
A fluorenyl, triphenylene, or 9, 9-dimethyl-2-fluorenyl group; the substituted or unsubstituted fused heterocyclic aromatic hydrocarbon group is quinoline, isoquinoline or quinazoline; the unsubstituted alkyl group is a methyl group, and the substituted alkyl group is a trifluoromethyl group. The substitution may be mono-or polysubstituted.
Preferably, the compound is of the formula (14) to (56):
the application of the polycyclic aromatic hydrocarbon derivative containing the naphthyridine group in an organic electroluminescent device.
The polycyclic aromatic hydrocarbon derivative containing the naphthyridine group can be used as an electron transport material.
An organic electroluminescent device comprises a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer which are sequentially formed on the substrate; the organic light-emitting functional layer comprises a hole transport layer, an organic light-emitting layer and an electron transport layer, and the electron transport material of the electron transport layer is the polycyclic aromatic hydrocarbon derivative containing the naphthyridine group.
EXAMPLE 1 Synthesis of various 3-bromo-7-aryl-1, 5-naphthyridine derivative intermediates
Synthesis of 1, 3-bromo-7-phenyl-1, 5-naphthyridine
A1000 ml three-neck flask is stirred by magnetic force and protected by nitrogen, 5.72g (286, 0.02mol) of 3, 7-dibromo-1, 5-naphthyridine, 2.7g (122, 0.022mol) of phenylboronic acid, 1.16g (1154, 0.001mol) of tetrakis ((triphenylphosphine) palladium), 80ml of 2M aqueous sodium carbonate solution, 80ml of toluene, 80ml of ethanol and argon are added for replacement, the mixture is refluxed at 80 ℃, the reaction is monitored by a Thin Layer Chromatography (TLC) method, after 4 hours, TLC finds that the reaction of the dibromide serving as the raw material is complete and only the monobromide product is generated, the temperature is reduced to 25 ℃, an organic layer is separated, evaporated to dryness, column chromatography separation is carried out, ethyl acetate/petroleum ether is leached, and 5.77g of target intermediate 3-bromo-7-phenyl-1, 5-naphthyridine is obtained, the molecular weight is 284.3% of yield.
Synthesis of 2, 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine
The reaction steps are the same as the synthesis of the 3-bromo-7-phenyl-1, 5-naphthyridine, except that the raw material phenylboronic acid is changed into naphthalene-1-boronic acid to obtain the intermediate 3-bromo-7- (naphthalene-1-yl) -1, 5-naphthyridine.
Synthesis of 3, 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine
The reaction steps are the same as the synthesis of the 3-bromo-7-phenyl-1, 5-naphthyridine, except that the raw material phenylboronic acid is changed into naphthalene-2-boronic acid to obtain the intermediate 3-bromo-7- (naphthalene-2-yl) -1, 5-naphthyridine.
Example 2
Synthesis of Compound represented by the formula (14)
A1000 ml jar was equipped with magnetic stirring, and 3-bromo-7-phenyl-1, 5-naphthyridine 5.68g (molecular weight 284, 0.02mol), 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid 11.0g (molecular weight 474, 0.022mol), tetrakis ((triphenylphosphine) palladium 1.16g (molecular weight 1154, 0.001mol), 2M aqueous sodium carbonate 80ml, toluene 80ml, ethanol 80ml, argon replacement, reflux at 80 deg.C, monitoring the reaction by Thin Layer Chromatography (TLC), after 3.5 hours TLC found that the starting bromide reacted completely, only the product spot was reduced, the organic layer was separated, evaporated to dryness, column chromatography was performed, ethyl acetate/petroleum ether elution provided 11.33g of the compound of formula (14), molecular weight 634, yield 89.3%.
Product MS (m/e): 634, elemental analysis (C)48H30N2): theoretical value C: 90.82%, H: 4.76%, N: 4.41 percent; found value C: 90.85%, H: 4.72%, N: 4.43 percent.
Example 3
Synthesis of Compound represented by the formula (15)
The procedure was as in example 2 except that 3-bromo-7-phenyl-1, 5-naphthyridine was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine and the other reagents were changed to give a compound represented by formula (15).
Product MS (m/e): 684 elemental analysis (C)52H32N2): theoretical value C: 91.20%, H: 4.71%, N: 4.09%; found value C: 91.23%, H: 4.73%, N: 4.04% of its nuclear magnetic spectrum (1HNMR) is shown in fig. 1.
Example 4
Synthesis of Compound represented by the formula (16)
The procedure was as in example 2 except that 3-bromo-7-phenyl-1, 5-naphthyridine was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine and the other reagents were changed to give a compound represented by formula (16).
Product MS (m/e): 684 elemental analysis (C)52H32N2): theoretical value C: 91.20%, H: 4.71%, N: 4.09%; found value C: 91.21%, H: 4.74%, N: 4.05 percent.
Example 5
Synthesis of Compound represented by the formula (17)
The procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to 9- (naphthalen-2-yl) anthracene-10-boronic acid, and the other reagents were changed to give a compound represented by formula (17).
Product MS (m/e): 558 elemental analysis (C)42H26N2): theoretical value C: 90.29%, H: 4.69%, N: 5.01 percent; found value C: 90.31%, H: 4.65%, N: 5.04 percent.
Example 6
Synthesis of Compound represented by the formula (18)
The procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to 9- (naphthalen-2-yl) anthracene-10-boronic acid, and the other reagents were changed to give a compound represented by formula (18).
Product MS (m/e): 558, yuanElemental analysis (C)42H26N2): theoretical value C: 90.29%, H: 4.69%, N: 5.01 percent; found value C: 90.32%, H: 4.66%, N: 5.02 percent.
Example 7
Synthesis of Compound represented by the formula (19)
The procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid, to p- (9- (naphthalen-2-yl) anthracen-10-yl) phenylboronic acid, and the other reagents were changed to give a compound represented by formula (19).
Product MS (m/e): 634, elemental analysis (C)48H30N2): theoretical value C: 90.82%, H: 4.76%, N: 4.41 percent; found value C: 90.84%, H: 4.73%, N: 4.43 percent.
Example 8
Synthesis of Compound represented by the formula (20)
The procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid, to p- (9- (naphthalen-2-yl) anthracen-10-yl) phenylboronic acid, and the other reagents were changed to give a compound represented by formula (20).
Product MS (m/e): 634, elemental analysis (C)48H30N2): theoretical value C: 90.82%, H: 4.76%, N: 4.41 percent; found value C: 90.84%, H: 4.73%, N: 4.43 percent.
Example 9
Synthesis of Compound represented by the formula (21)
The procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to 9- (naphthalen-1-yl) anthracene-10-boronic acid, and the other reagents were changed to give a compound represented by formula (21).
Product MS (m/e): 558 elemental analysis (C)42H26N2): theoretical value C: 90.29%, H: 4.69%, N: 5.01 percent; found value C: 90.31%, H: 4.65%, N: 5.04 percent.
Example 10
Synthesis of Compound represented by the formula (22)
The procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-1-yl) anthracene-2-boronic acid to 9- (naphthalen-1-yl) anthracene-10-boronic acid, and the other reagents were changed to give a compound represented by formula (22).
Product MS (m/e): 558 elemental analysis (C)42H26N2): theoretical value C: 90.29%, H: 4.69%, N: 5.01 percent; found value C: 90.27%, H: 4.68%, N: 5.05 percent.
Example 11
Synthesis of Compound represented by the formula (23)
The procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid, to p- (9- (naphthalen-1-yl) anthracen-10-yl) phenylboronic acid, and the other reagents were changed to give a compound represented by formula (23).
Product MS (m/e): 634, elemental analysis (C)48H30N2): theoretical value C: 90.82%, H: 4.76%, N: 4.41 percent; found value C: 90.83%, H: 4.74%, N: 4.43 percent.
Example 12
Synthesis of Compound represented by the formula (24)
The procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid, to p- (9- (naphthalen-1-yl) anthracen-10-yl) phenylboronic acid, and the other reagents were changed to give a compound represented by formula (24).
Product MS (m/e): 634, elemental analysis (C)48H30N2): theoretical value C: 90.82%, H: 4.76%, N: 4.41 percent; found value C: 90.85%, H: 4.73%, N: 4.42 percent.
Example 13
Synthesis of Compound represented by the formula (25)
The synthesis procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to p- (9- (9, 9-dimethyl-9H-fluoren-2-yl) anthracen-10-yl) phenylboronic acid, and the other reagents were changed to give the compound represented by formula (25).
Product MS (m/e): 700, elemental analysis (C)53H36N2): theoretical value C: 90.83%, H: 5.18%, N: 4.00 percent; found value C: 90.85%, H: 5.12%, N: 4.03% of its nuclear magnetic spectrum (1HNMR) is shown in fig. 2.
Example 14
Synthesis of Compound represented by the formula (26)
The synthesis procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to p- (9- (9, 9-dimethyl-9H-fluoren-2-yl) anthracen-10-yl) phenylboronic acid, and the other reagents were changed to give a compound represented by formula (26).
Product MS (m/e): 700, elemental analysis (C)53H36N2): theoretical value C: 90.83%, H: 5.18%, N: 4.00 percent; found value C: 90.81%, H: 5.14%, N: 4.05 percent.
Example 15
Synthesis of Compound represented by the formula (27)
The synthesis procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to 9- (9, 9-dimethyl-9H-fluoren-2-yl) anthracene-10-boronic acid, and the other reagents were changed to give a compound represented by formula (27).
Product MS (m/e): 624, elemental analysis (C)47H32N2): theoretical value C: 90.35%, H: 5.16%, N: 4.48 percent; found value C: 90.37%, H: 5.13%, N: 4.50 percent.
Example 16
Synthesis of Compound represented by the formula (28)
The synthesis procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to 9- (9, 9-dimethyl-9H-fluoren-2-yl) anthracene-10-boronic acid, and the other reagents were changed to give the compound represented by formula (28).
Product MS (m/e): 624, elemental analysis (C)47H32N2): theoretical value C: 90.35%, H: 5.16%, N: 4.48 percent; found value C: 90.33%, H: 5.15%, N: 4.52 percent.
Example 17
Synthesis of Compound represented by the formula (29)
The synthesis procedure was the same as in example 2 except that 3-bromo-7-phenyl-1, 5-naphthyridine was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid was changed to anthracene-9, 10-diboronic acid, and the other reagents were unchanged to obtain a compound represented by formula (29).
Product MS (m/e): 686 elemental analysis (C)47H32N2): theoretical value C: 87.44%, H: 4.40%, N: 8.16 percent; found value C: 87.42%, H: 4.44%, N: 8.14 percent.
Example 18
Synthesis of Compound represented by the formula (30)
The synthesis procedure was the same as in example 2 except that 3-bromo-7-phenyl-1, 5-naphthyridine was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid was changed to anthracene-9, 10-diboronic acid, and the other reagents were unchanged to obtain the compound represented by formula (30).
Product MS (m/e): 686 elemental analysis (C)47H32N2): theoretical value C: 87.44%, H: 4.40%, N: 8.16 percent; found value C: 87.45%, H: 4.42%, N: 8.13 percent.
Example 19
Synthesis of Compound represented by the formula (31)
The procedure was the same as in example 2 except that 3-bromo-7-phenyl-1, 5-naphthyridine as a starting material was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine, and 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to 7, 12-diphenylbenzo [ k ] fluoranthene-3-boronic acid, and the other reagents were changed to give a compound represented by formula (31).
Product MS (m/e): 658 elemental analysis (C)50H30N2): theoretical value C: 91.16%, H: 4.59%, N: 4.25 percent; found value C: 91.14%, H: 4.62%, N: 4.24 percent.
Example 20
Synthesis of Compound represented by the formula (32)
The procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to 7, 12-diphenylbenzo [ k ] fluoranthene-3-boronic acid, and the other reagents were changed to give a compound represented by formula (32).
Product MS (m/e): 658 elemental analysis (C)50H30N2): theoretical value C: 91.16%, H: 4.59%, N: 4.25 percent; found value C: 91.13%, H: 4.61%, N: 4.26 percent.
Example 21
Synthesis of Compound represented by the formula (33)
The procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to p- (7, 12-diphenylbenzo [ k ] fluoranthen-3-yl) phenylboronic acid, and the other reagents were changed to give a compound represented by formula (33).
Product MS (m/e): 734, elemental analysis (C)56H34N2): theoretical value C: 91.52%, H: 4.66%, N: 3.81 percent; found value C: 91.54%, H: 4.63%, N: 3.83% of its nuclear magnetic spectrum (1HNMR) is shown in fig. 3.
Example 22
Synthesis of Compound represented by the formula (34)
The procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to p- (7, 12-diphenylbenzo [ k ] fluoranthen-3-yl) phenylboronic acid, and the other reagents were changed to give a compound represented by formula (34).
Product MS (m/e): 734, elemental analysis (C)56H34N2): theoretical value C: 91.52%, H: 4.66%, N: 3.81 percent; found value C: 91.50%, H: 4.64%, N: 3.86 percent.
Example 23
Synthesis of Compound represented by the formula (35)
The procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine, and 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to 12-naphthalenyl
-6-boronic acid, with the other reagents unchanged, to give the compound of formula (35).
Product MS (m/e): 608, elemental analysis (C)46H28N2): theoretical value C: 90.76%, H: 4.64%, N: 4.60 percent; found value C: 90.75%, H: 4.62%, N: 4.63 percent.
Example 24
Synthesis of Compound represented by the formula (36)
The procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine, and 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to 12- (naphthalen-2-yl)
-6-boronic acid, and the other reagents are unchanged to give the compound represented by formula (36).
Product MS (m/e): 608, elemental analysis (C)46H28N2): theoretical value C: 90.76%, H: 4.64%, N: 4.60 percent; found value C: 90.73%, H: 4.63%, N: 4.64 percent.
Example 25
Synthesis of Compound represented by the formula (37)
The procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine, and 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to 12- (naphthalen-1-yl)
-6-boronic acid, with the other reagents unchanged, to give the compound of formula (37).
Product MS (m/e): 608, elemental analysis (C)46H28N2): theoretical value C: 90.76%, H: 4.64%, N: 4.60 percent; found value C: 90.75%, H: 4.62 percent of the total weight of the steel,N：4.63％。
example 26
Synthesis of Compound represented by the formula (38)
The procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine, and 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to 12- (naphthalen-1-yl)
-6-boronic acid, with the other reagents unchanged, to give the compound represented by formula (38).
Product MS (m/e): 608, elemental analysis (C)46H28N2): theoretical value C: 90.76%, H: 4.64%, N: 4.60 percent; found value C: 90.77%, H: 4.61%, N: 4.62% of its nuclear magnetic spectrum (1HNMR) is shown in fig. 4.
Example 27
Synthesis of Compound represented by the formula (39)
The procedure was the same as in example 2 except that 3-bromo-7-phenyl-1, 5-naphthyridine as the starting material was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine and 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to 12- (9, 9-dimethyl-9H-fluoren-2-yl)
-6-boronic acid, and the other reagents are unchanged to obtain the compound represented by the formula (39).
Product MS (m/e): 674, elemental analysis (C)51H34N2): theoretical value C: 90.77%, H: 5.08%, N: 4.15 percent; found value C: 90.74%, H: 5.07%, N: 4.19 percent.
Example 28
Synthesis of Compound represented by the formula (40)
The procedure was the same as in example 2 except that 3-bromo-7-phenyl-1, 5-naphthyridine as the starting material was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine and 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to 12- (9, 9-dimethyl-9H-fluoren-2-yl)
-6-boronic acid, with the other reagents unchanged, to give the formula(40) The compounds shown.
Product MS (m/e): 674, elemental analysis (C)51H34N2): theoretical value C: 90.77%, H: 5.08%, N: 4.15 percent; found value C: 90.75%, H: 5.07%, N: 4.18 percent.
Example 29
Synthesis of Compound represented by the formula (41)
The procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine, and 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid, was changed to p- (12- (naphthalen-2-yl)
-6-yl) phenylboronic acid with the remaining reagents unchanged to give the compound of formula (41).
Product MS (m/e): 684 elemental analysis (C)52H32N2): theoretical value C: 91.20%, H: 4.71%, N: 4.09%; found value C: 91.22%, H: 4.74%, N: 4.04 percent.
Example 30
Synthesis of Compound represented by the formula (42)
The procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine, and 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid, was changed to p- (12- (naphthalen-2-yl)
-6-yl) phenylboronic acid with the remaining reagents unchanged to give the compound of formula (42).
Product MS (m/e): 684 elemental analysis (C)52H32N2): theoretical value C: 91.20%, H: 4.71%, N: 4.09%; found value C: 91.24%, H: 4.73%, N: 4.03 percent.
Example 31
Synthesis of Compound represented by the formula (43)
The procedure was the same as in example 2 except that 3-bromo-7-phenyl-1, 5-naphthyridine as the starting material was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to 6- (naphthalen-2-yl) pyrene-1-boronic acid, and the other reagents were changed to give the compound represented by formula (43).
Product MS (m/e): 582, elemental analysis (C)44H26N2): theoretical value C: 90.69%, H: 4.50%, N: 4.81 percent; found value C: 90.64%, H: 4.52%, N: 4.83 percent.
Example 32
Synthesis of Compound represented by the formula (44)
The synthesis procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to 6- (naphthalen-2-yl) pyrene-1-boronic acid, and the other reagents were unchanged to give the compound represented by formula (44).
Product MS (m/e): 582, elemental analysis (C)44H26N2): theoretical value C: 90.69%, H: 4.50%, N: 4.81 percent; found value C: 90.67%, H: 4.51%, N: 4.82 percent.
Example 33
Synthesis of Compound represented by the formula (45)
The synthesis procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid to 6- (naphthalen-1-yl) pyrene-1-boronic acid, and the other reagents were unchanged to give the compound represented by formula (45).
Product MS (m/e): 582, elemental analysis (C)44H26N2): theoretical value C: 90.69%, H: 4.50%, N: 4.81 percent; found value C: 90.63%, H: 4.53%, N: 4.84 percent.
Example 34
Synthesis of Compound represented by the formula (46)
The synthesis procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid, to 6- (naphthalen-1-yl) pyrene-1-boronic acid, and the other reagents were unchanged to give the compound represented by formula (46).
Product MS (m/e): 582, elemental analysis (C)44H26N2): theoretical value C: 90.69%, H: 4.50%, N: 4.81 percent; measured valueC：90.64％，H：4.51％，N：4.85％。
Example 35
Synthesis of Compound represented by the formula (47)
The synthesis procedure was the same as in example 2 except that 3-bromo-7-phenyl-1, 5-naphthyridine was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid was changed to 6- (9, 9-dimethyl-9H-fluoren-2-yl) pyrene-1-boronic acid, and the other reagents were changed to obtain the compound represented by formula (47).
Product MS (m/e): 648 elemental analysis (C)49H32N2): theoretical value C: 90.71%, H: 4.97%, N: 4.32 percent; found value C: 90.73%, H: 4.93%, N: 4.34 percent.
Example 36
Synthesis of Compound represented by the formula (48)
The synthesis procedure was the same as in example 2 except that 3-bromo-7-phenyl-1, 5-naphthyridine was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid was changed to 6- (9, 9-dimethyl-9H-fluoren-2-yl) pyrene-1-boronic acid, and the other reagents were changed to obtain the compound represented by formula (48).
Product MS (m/e): 648 elemental analysis (C)49H32N2): theoretical value C: 90.71%, H: 4.97%, N: 4.32 percent; found value C: 90.74%, H: 4.93%, N: 4.33 percent.
Example 37
Synthesis of Compound represented by the formula (49)
The synthesis procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid, was changed to p- (6- (naphthalen-2-yl) pyrene-1-yl) phenylboronic acid, and the other reagents were changed to give the compound represented by formula (49).
Product MS (m/e): 658 elemental analysis (C)50H30N2): theoretical value C: 91.16%, H: 4.59%, N: 4.25 percent; found value C: 91.14%, H: 4.57%, N: 4.29% of its nuclear magnetic spectrum (1HNMR) is shown in fig. 5.
Example 38
Synthesis of Compound represented by the formula (50)
The synthesis procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid, was changed to p- (6- (naphthalen-2-yl) pyrene-1-yl) phenylboronic acid, and the other reagents were unchanged to give the compound represented by formula (50).
Product MS (m/e): 658 elemental analysis (C)50H30N2): theoretical value C: 91.14%, H: 4.57%, N: 4.29 percent; found value C: 91.16%, H: 4.58%, N: 4.26 percent.
Example 39
Synthesis of Compound represented by the formula (51)
The synthesis procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid, was changed to p- (6- (naphthalen-2-yl) pyrene-1-yl) phenylboronic acid, and the other reagents were changed to give the compound represented by formula (51).
Product MS (m/e): 684 elemental analysis (C)52H32N2): theoretical value C: 91.20%, H: 4.71%, N: 4.09%; found value C: 91.23%, H: 4.73%, N: 4.04 percent.
Example 40
Synthesis of Compound represented by the formula (52)
The synthesis procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid, to p- (7- (naphthalen-2-yl) triphenylen-2-yl) phenylboronic acid, and the conditions for other drugs, reagents, reactions, separations, and the like were unchanged to obtain the compound represented by formula (52).
Product MS (m/e): 684 elemental analysis (C)52H32N2): theoretical value C: 91.20%, H: 4.71%, N: 4.09%; found value C: 91.22%, H: 4.73%, N: 4.05%, its nuclear magnetic spectrum (1HNMR) is shown in fig. 6.
EXAMPLE 41
Synthesis of Compound represented by the formula (53)
The synthesis procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-2-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid, to 7- (naphthalen-2-yl) triphenylene-2-boronic acid, and the conditions for other drugs, reagents, reactions, separations, and the like were unchanged to give the compound represented by formula (53).
Product MS (m/e): 608, elemental analysis (C)46H28N2): theoretical value C: 90.76%, H: 4.64%, N: 4.60 percent; found value C: 90.72%, H: 4.65%, N: 4.63 percent.
Example 42
Synthesis of Compound represented by the formula (54)
The synthesis procedure was the same as in example 2 except that the starting material, 3-bromo-7-phenyl-1, 5-naphthyridine, was changed to 3-bromo-7- (naphthalen-1-yl) -1, 5-naphthyridine, 9, 10-di (naphthalen-2-yl) anthracene-2-boronic acid, to 7- (naphthalen-2-yl) triphenylene-2-boronic acid, and the conditions for other drugs, reagents, reactions, separations, and the like were unchanged to give the compound represented by formula (54).
Product MS (m/e): 608, elemental analysis (C)46H28N2): theoretical value C: 90.76%, H: 4.64%, N: 4.60 percent; found value C: 90.73%, H: 4.65%, N: 4.62 percent.
The following are examples of the use of the compounds of the invention:
example 43
To facilitate comparison of the transport properties of these electron transport materials, the present inventors designed a simple electroluminescent device using EM1 as the emissive material (EM1 is the host material and not the emissive material in order not to pursue high efficiency but to verify the possibility of these materials being practical) and using the high efficiency electron transport material Bphen as the comparative material. The structures of EM1 and Bphen are:
the structure of the organic electroluminescent device in the embodiment of the invention is as follows:
substrate/anode/Hole Transport Layer (HTL)/organic light Emitting Layer (EL)/Electron Transport Layer (ETL)/cathode.
The substrate may be a substrate used in a conventional organic light emitting device, for example: glass or plastic. In the invention, the glass substrate and the ITO are used as anode materials in the manufacture of the organic electroluminescent device.
Various triarylamine-based materials may be used for the hole transport layer. The hole transport material selected for use in the fabrication of the organic electroluminescent device of the present invention is NPB. The NPB structure is:
the cathode can adopt a metal and a mixture structure thereof, such as Mg: ag. Ca: ag, etc., or an electron injection layer/metal layer structure, such as LiF/Al, Li2O/Al and the like. The cathode material selected in the preparation of the organic electroluminescent device is LiF/Al.
The compound in this embodiment is used as an electron transport material in an organic electroluminescent device, and the EML is used as a light emitting layer material, so that a plurality of organic electroluminescent devices are prepared, and the structure of each organic electroluminescent device is as follows: ITO/NPB (40nm)/EM1(30nm)/ETL material (20nm)/LiF (0.5nm)/Al (150 nm);
in one comparative organic electroluminescent device, Bphen was used as the electron transport material, and the materials of the present invention were used for the remaining organic electroluminescent devices.
The preparation process of the organic electroluminescent device in the embodiment is as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, performing vacuum evaporation on the anode layer film to form NPB as a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 40 nm;
vacuum evaporating EM1 on the hole transport layer to serve as a light emitting layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30 nm;
a compound represented by a one-layer type (14), a formula (15), a formula (18), a formula (22), a formula (27), a formula (29), a formula (31), a formula (36), a formula (43) or a formula (53) is vacuum-evaporated on the light-emitting layer to be used as an electron transport layer material of the device, Bphen is used as a contrast material of the electron transport layer material of the device, the evaporation rate is 0.1nm/s, and the total thickness of the evaporated film is 20 nm;
LiF with the thickness of 0.5nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 150nm is used as a cathode of the device.
The organic electroluminescent device properties are given in the following table:
| compound numbering | Required luminance cd/m2 | Voltage V | Current efficiency cd/A |
| Bphen | 1000.00 | 6.2 | 6.1 |
| Formula (14) | 1000.00 | 5.6 | 7.1 |
| Formula (15) | 1000.00 | 5.6 | 6.9 |
| Formula (18) | 1000.00 | 5.7 | 7.0 |
| Formula (22) | 1000.00 | 5.8 | 7.0 |
| Formula (27) | 1000.00 | 5.7 | 7.1 |
| Formula (29) | 1000.00 | 5.7 | 6.9 |
| Formula (31) | 1000.00 | 5.6 | 7.1 |
| Formula (36) | 1000.00 | 5.7 | 7.1 |
| Formula (43) | 1000.00 | 5.7 | 7.0 |
| Formula (53) | 1000.00 | 5.7 | 7.1 |
The results show that the novel organic material is used for the organic electroluminescent device, can effectively reduce the working voltage of the device and improve the current efficiency, and is an electron transport material with good performance. Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the invention, and the scope of the invention is outlined by the appended claims.
Claims (5)
1. A polycyclic aromatic hydrocarbon derivative containing a naphthyridine group, characterized by having a structure represented by the following formulae (8) to (13):
in the above formulae (8) to (13), Ar1Selected from phenyl, naphthyl, fluorenyl, 9-dimethyl-2-fluorenyl;
Ar2selected from phenyl, naphthyl, H;
l is a single bond;
R3to R13Is selected from H;
R1selected from H, R2Selected from aromatic hydrocarbon groups, condensed ring aromatic hydrocarbon groups;
the aryl is phenyl, o-tolyl, p-tolyl or tert-butylphenyl; the condensed ring aromatic hydrocarbon group is naphthyl, phenanthryl, anthryl, pyrenyl,
A fluorenyl group, a triphenylene group or a 9, 9-dimethyl-2-fluorenyl group.
2. A fused ring aromatic hydrocarbon derivative containing a naphthyridine group, wherein the compound has the structure shown below:
3. use of a polycyclic aromatic hydrocarbon derivative containing a naphthyridine group according to claim 1 or 2 in an organic electroluminescent device.
4. The use of a naphthyridine group containing polycyclic aromatic hydrocarbon derivative in an organic electroluminescent device according to claim 3, wherein the naphthyridine group containing polycyclic aromatic hydrocarbon derivative is useful as an electron transport material.
5. An organic electroluminescent device comprises a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer which are sequentially formed on the substrate; the organic light-emitting functional layer comprises a hole transport layer, an organic light-emitting layer and an electron transport layer, and is characterized in that:
the electron transport material of the electron transport layer is the polycyclic aromatic hydrocarbon derivative containing a naphthyridine group according to claim 1 or 2.
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