1,4-disubstituted naphthalene derivative and application

Abstract

The invention provides a 1,4-disubstituted naphthalene derivative. The general compound is as shown in the following formula I (the formula I is as shown in the description); in the formula I, R' is selected from hydrogen, halogen, and substituted or unsubstituted C1-C30 alkyl; Ar1 is selected from hydrogen, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 naphthenic base, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heterocyclic aryl; Ar2 is as shown in the following formula II (the formula II is as shown in the description); in the formula II, each of R1-R5 is selected from hydrogen, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 naphthenic base, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heterocyclic aryl; and at least one of R1-R5 is not hydrogen.

Description

technical field

[0001] The invention relates to a class of compounds with general formulas with special properties, in particular to a compound used in the fields of electronic devices and optical films. Background technique

[0002] When a substance is irradiated by incident light of a certain wavelength (usually ultraviolet rays or X-rays), it absorbs light energy and enters an excited state, then undergoes a delay and emits outgoing light with a longer wavelength than the incident light. Luminescent phenomena are generally divided into fluorescence and phosphorescence, and their luminescent principles are different. Many inorganic and organic materials have this property, and are widely used in various fields, such as lighting, biochemical medicine, detection, etc. Compared with inorganic materials, organic materials have more possibilities for structural optimization, more combination schemes can be given, and the emission color can also cover the entire visible light r...

Examples

Embodiment 1

[0038] Synthesis of Compound C1

[0039]

[0040] 1,4-dibromo-3,7-diisopropylnaphthalene (3.69g, 10mmol), N-phenyl-(9-Nphenyl-benzocarbazole)amine (8.4g, 22mmol), tert-butyl Sodium alkoxide 10.0g (10mmol, 5.0eq), toluene 500mL, nitrogen gas under the liquid surface of the solution for 30min, then add Pd2 (dba) 31.2g (2mmol, 2%eq), inject 10% tri-tert-butylphosphine 4ml with a syringe ( 2mmol, 2%eq), start stirring, heat to 100 degrees Celsius, react for 6h, the reaction is complete, the reaction solution is concentrated, separated by column chromatography (petroleum ether: ethyl acetate = 50:1 ~ 10:1), to obtain light yellow 7.9 g of solid, yield 74.7%.

[0041] 1 H NMR(400MHz,Chloroform)δ9.89(s,3H),9.36(s,3H),8.54(s,3H),8.28(s,6H),7.90(dd,J=26.5,12.3Hz,15H) ,8.03–7.65(m,25H),7.60(d,J=16.0Hz,17H),7.49(d,J=8.0Hz,18H),7.25(d,J=12.0Hz,14H),7.16(d, J=16.0Hz, 7H), 7.10–6.84(m, 27H), 6.40(s, 3H), 2.87(s, 2H), 1.25(d, J=12.0Hz, 36H).

Embodiment 2

[0043] Synthesis of compound C2

[0044] Compound C2 was prepared in the same manner as in Example 1, except that N-phenyl-(9-Nphenyl-benzocarbazole)amine was replaced by equivalent N-phenyl-(9-Nphenyl- 3-tribenzocarbazol) amine, replacing 1,4-dibromo-3,7-diisopropylnaphthalene with an equivalent amount of 1,4-dibromo-2,6-dimethylnaphthalene, after the reaction is complete , 8.2 g of a light yellow solid was isolated with a yield of 78.2%.

[0045] 1 H NMR (400MHz, Chloroform) δ9.96(s,3H),9.60(s,6H),9.41(s,3H),9.23(s,3H),9.15(t,J=29.6Hz,12H),8.13 (s,3H),7.94(s,3H),7.70(d,J=4.0Hz,13H),7.66–7.55(m,28H),7.51(d,J=8.0Hz,22H),7.25(d, J=12.0Hz, 14H), 7.16(d, J=16.0Hz, 7H), 7.04(dd, J=26.0, 6.0Hz, 27H), 6.40(s, 3H), 2.70(s, 9H), 2.41( s,9H).

Embodiment 3

[0047] Synthesis of Compound C3

[0048] Compound C3 was prepared in the same manner as in Example 1, except that N-phenyl-(9-Nphenyl-benzocarbazole)amine was replaced by an equivalent amount of 2,8-diisoamylcarbazolamine, Replace 1,4-dibromo-3,7-diisopropylnaphthalene with an equivalent amount of 1,4-dibromo-2,6-di-tert-butylnaphthalene. After the reaction is completed, 7.2 g of a light yellow solid is isolated , the yield was 68.2%.

[0049] 1 H NMR (400MHz, Chloroform)δ8.25(s,1H),8.00–7.77(m,5H),7.74–7.46(m,4H),7.44(s,1H),7.11(d,J=0.4Hz, 2H), 7.02(dd, J=68.3, 12.1Hz, 5H), 2.61(s, 6H), 1.80–1.44(m, 21H), 1.40(s, 9H), 0.90(s, 15H).

technical field

[0001] The invention relates to a class of compounds with general formulas with special properties, in particular to a compound used in the fields of electronic devices and optical films. Background technique

[0002] When a substance is irradiated by incident light of a certain wavelength (usually ultraviolet rays or X-rays), it absorbs light energy and enters an excited state, then undergoes a delay and emits outgoing light with a longer wavelength than the incident light. Luminescent phenomena are generally divided into fluorescence and phosphorescence, and their luminescent principles are different. Many inorganic and organic materials have this property, and are widely used in various fields, such as lighting, biochemical medicine, detection, etc. Compared with inorganic materials, organic materials have more possibilities for structural optimization, more combination schemes can be given, and the emission color can also cover the entire visible light r...

Examples

Embodiment 1

[0038] Synthesis of Compound C1

[0039]

[0040] 1,4-dibromo-3,7-diisopropylnaphthalene (3.69g, 10mmol), N-phenyl-(9-Nphenyl-benzocarbazole)amine (8.4g, 22mmol), tert-butyl Sodium alkoxide 10.0g (10mmol, 5.0eq), toluene 500mL, nitrogen gas under the liquid surface of the solution for 30min, then add Pd2 (dba) 31.2g (2mmol, 2%eq), inject 10% tri-tert-butylphosphine 4ml with a syringe ( 2mmol, 2%eq), start stirring, heat to 100 degrees Celsius, react for 6h, the reaction is complete, the reaction solution is concentrated, separated by column chromatography (petroleum ether: ethyl acetate = 50:1 ~ 10:1), to obtain light yellow 7.9 g of solid, yield 74.7%.

[0041] 1 H NMR(400MHz,Chloroform)δ9.89(s,3H),9.36(s,3H),8.54(s,3H),8.28(s,6H),7.90(dd,J=26.5,12.3Hz,15H) ,8.03–7.65(m,25H),7.60(d,J=16.0Hz,17H),7.49(d,J=8.0Hz,18H),7.25(d,J=12.0Hz,14H),7.16(d, J=16.0Hz, 7H), 7.10–6.84(m, 27H), 6.40(s, 3H), 2.87(s, 2H), 1.25(d, J=12.0Hz, 36H).

Embodiment 2

[0043] Synthesis of compound C2

[0044] Compound C2 was prepared in the same manner as in Example 1, except that N-phenyl-(9-Nphenyl-benzocarbazole)amine was replaced by equivalent N-phenyl-(9-Nphenyl- 3-tribenzocarbazol) amine, replacing 1,4-dibromo-3,7-diisopropylnaphthalene with an equivalent amount of 1,4-dibromo-2,6-dimethylnaphthalene, after the reaction is complete , 8.2 g of a light yellow solid was isolated with a yield of 78.2%.

[0045] 1 H NMR (400MHz, Chloroform) δ9.96(s,3H),9.60(s,6H),9.41(s,3H),9.23(s,3H),9.15(t,J=29.6Hz,12H),8.13 (s,3H),7.94(s,3H),7.70(d,J=4.0Hz,13H),7.66–7.55(m,28H),7.51(d,J=8.0Hz,22H),7.25(d, J=12.0Hz, 14H), 7.16(d, J=16.0Hz, 7H), 7.04(dd, J=26.0, 6.0Hz, 27H), 6.40(s, 3H), 2.70(s, 9H), 2.41( s,9H).

Embodiment 3

[0047] Synthesis of Compound C3

[0048] Compound C3 was prepared in the same manner as in Example 1, except that N-phenyl-(9-Nphenyl-benzocarbazole)amine was replaced by an equivalent amount of 2,8-diisoamylcarbazolamine, Replace 1,4-dibromo-3,7-diisopropylnaphthalene with an equivalent amount of 1,4-dibromo-2,6-di-tert-butylnaphthalene. After the reaction is completed, 7.2 g of a light yellow solid is isolated , the yield was 68.2%.

[0049] 1 H NMR (400MHz, Chloroform)δ8.25(s,1H),8.00–7.77(m,5H),7.74–7.46(m,4H),7.44(s,1H),7.11(d,J=0.4Hz, 2H), 7.02(dd, J=68.3, 12.1Hz, 5H), 2.61(s, 6H), 1.80–1.44(m, 21H), 1.40(s, 9H), 0.90(s, 15H).

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