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Bismaleimide containing 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) and asymmetric in molecular structure as well as preparation method and application of bismaleimide in preparation of composite resin

A technology of bismaleimide and molecular structure, which is applied in the field of microelectronic packaging materials, can solve the problems of reducing resin performance, reducing heat resistance, and difficulty in meeting flame retardant requirements, and achieves the effect of solving poor solubility

Active Publication Date: 2015-03-25
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The introduction of the third component improves the solubility and processability of BT resin, but also reduces its heat resistance, so that its glass transition temperature is only maintained at 200°C-300°C, and the long-term use temperature does not exceed 230°C
Although BT resin contains nitrogen, it can release some non-combustible and non-combustible gases when burning, and has certain self-extinguishing properties, but it is still difficult to meet the requirements of flame retardancy
Adding components such as flame retardant inorganic fillers to BT resin will reduce the original properties of the resin, such as processability, dielectric properties, etc.

Method used

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  • Bismaleimide containing 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) and asymmetric in molecular structure as well as preparation method and application of bismaleimide in preparation of composite resin
  • Bismaleimide containing 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) and asymmetric in molecular structure as well as preparation method and application of bismaleimide in preparation of composite resin
  • Bismaleimide containing 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) and asymmetric in molecular structure as well as preparation method and application of bismaleimide in preparation of composite resin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1 Preparation of asymmetric dibasic primary amines containing DOPO

[0048] The asymmetric dibasic primary amine containing DOPO shown in general formula (I) is carried out with reference to the method disclosed in the existing literature (Journal of Polymer Science: Part A: Polymer Chemistry, Vol.49, 1331-1340 (2011)) Preparation, the synthetic route is shown in the following formula:

[0049]

[0050] Among them, R 1 is a hydrogen atom, C 1 -C 6 Alkyl, C 1 -C 6 Alkoxy, -CF 3 or a halogen atom;

[0051] R 2 is a hydrogen atom, methyl, 2,6-dimethyl, methoxy or allyl;

[0052] R3 is a hydrogen atom, methyl, 2,6-dimethyl, ethyl or methoxy;

[0053] R 4 is a hydrogen atom, C 1 -C 6 Alkyl, -CF 3 or benzene ring;

[0054] X is O or S;

[0055] x 1 is OH or SH;

[0056] x 2 is F or Cl;

[0057] with R 1 , R 2 and R 3 Take hydrogen atom, R respectively 4 Take -CH 3 , X takes O, X 1 Take OH, X 2 Taking F as an example, the detailed synthetic...

Embodiment 2

[0062] Example 2 Preparation of Bismaleimide Monomer Containing DOPO and Asymmetric Molecular Structure by Method 1

[0063] with R 1 , R 2 , R 3 and R 5 Take hydrogen atom, R respectively 4 Take -CH 3 , X takes O, and the mixed solvent containing toluene takes toluene / DMF (volume ratio is 2 / 1) mixed solution as example, through the first kind of preparation method provided by the present invention, with the formula (I- 1) The asymmetric dibasic primary amine containing DOPO shown in 1) prepares the compound shown in the following formula (II-1):

[0064] 1-(4'-maleimidophenyl)-1-(4'-(4"-maleimidophenoxy)phenyl-1-(10'-(9',10 '-Dihydro-9'-oxa-10'-phosphaphenanthrene-10'-oxide) ethane,

[0065] 1-(4'-maleimido)phenyl-1-[4'-(4”-maleimido)phenoxyl]phenyl-1-[(9,10-dih ydro-9-oxa-10-phosphaphenanthrene)-10-yl] ethane:

[0066]

[0067] Weigh 5.18g (0.01mol) of the formula (I-1) prepared in Example 1 containing DOPO dibasic primary amine, and add 1.96g (0.02mol) of maleic...

Embodiment 3

[0070] Embodiment 3 Further preparation of cyanate ester composite resin with the monomers prepared in Example 2

[0071] The bismaleimide monomer containing DOPO shown in the formula (II-1) prepared in Example 2 is used to prepare BT composite resin, the cyanate is bisphenol A cyanate, and no allylphenols are added. Compounds, epoxy resins, catalysts:

[0072] Weigh 80 parts by mass of the bismaleimide shown in formula (II-1) prepared in Example 1 and 20 parts by mass of bisphenol A cyanate, melt and blend for 10 minutes at 140 ° C and immediately pour into aluminum and degassed at 180°C. After no obvious air bubbles, cured at 230°C for 2 hours and 300°C for 8 hours to obtain cured BT resin.

[0073] The BT composite resin prepared in this example has good solubility and can be dissolved in low boiling point and low toxicity solvents such as methanol, acetone, methylene chloride and tetrahydrofuran, and has high modulus and high glass transition temperature after curing , the...

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Abstract

The invention relates to the field of micro-electronic packaging materials, and discloses bismaleimide containing 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) and asymmetric in molecular structure, as shown in a general formula (II) shown in specification, as well as a preparation method and application of the bismaleimide in preparation of composite resin. The bismaleimide containing DOPO and asymmetric in molecular structure disclosed by the invention is soluble in such conventional organic solvents as acetone, so as to facilitate processing and using; the bismaleimide containing DOPO and asymmetric in molecular structure disclosed by the invention can be used for further preparing cyanate ester composite resin, and a cured product is good in thermal stability and flame retardance; and as a base material for packaging in the micro-electronic packaging field, the bismaleimide has good application prospect.

Description

technical field [0001] The invention belongs to the field of microelectronic packaging materials, and in particular relates to a bismaleimide monomer structure containing DOPO and an asymmetric molecular structure, a method for preparing the monomer structure and the use of the monomer structure in preparing bismaleimide Applications in amine-cyanate composite resins. Background technique [0002] Packaging substrate plays an important role in supporting, protecting and interconnecting in microelectronic packaging. With the continuous development of microelectronic packaging technology, packaging substrate materials need to have better performance, such as higher dimensional stability, lower Dielectric constant, higher glass transition temperature and excellent flame retardancy. Especially with the use of lead-free solder, the peak temperature of reflow soldering has increased to above 250°C, which requires the substrate material to have a higher glass transition temperatur...

Claims

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Application Information

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IPC IPC(8): C07F9/6574C08G73/12C08G73/06C08G59/42
Inventor 任志东肖斐
Owner FUDAN UNIV
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