PROBLEM TO BE SOLVED: To provide a phenolic hydroxyl group-containing resin having high thermal conductivity, excellent in adhesiveness to a substrate, flexibility and heat resistance, and useful as a matrix resin for a TIM (thermal interface material) or other electronic equipment materials, and to provide a production method of the phenolic hydroxyl group-containing resin, a curable resin composition, a cured product of the composition, and a heat-radiation resin material.SOLUTION: The phenolic hydroxyl group-containing resin has a molecular structure expressed by general formula (I) shown below. In the formula, A each independently represents a linear or branched alkylene group; Q each independently represents an organic group having a plurality of aromatic nuclei; l represents an integer of 1 to 10; and m represents an integer of 1 to 5.