Synthesis of TPD-containing polymers for use as light-emitting materials in electroluminescent and laser devices

Abstract

The synthesis of two families of electrically active and highly luminescent TPD-based copolymers is reported. (1) The Horner-olefination between TPD-dialdehydes and xylylene bisphosphonates has been used to prepare red and green emitting conjugated TPD-PPV copolymers 1 - 4. Here the TPD (triphenylamine dimer) moieties are brigded through alkoxy- substituted p-phenylene vinylene segments. (2) Blue emitting, nonconjugated TPD-xylylene copolymers (Poly-TPD- DPX 5, (6) have been synthesized by an electrophilic aralkylation using diphenylxylylene diol and TPD as the monomers. All these TPD-copolymers constitute amorphous electro-optical materials possessing remarkably high glass transition temperatures (Tg 110 - 240 degrees Celsius). Here we demonstrate strong lasing in the red, green and blue spectral region employing thin layers (approximately 100 nm) of these solution processable polymeric materials. In waveguiding neat films traveling-wave lasing (amplified spontaneous emission -- ASE) is achieved upon picosecond pulse excitation at 347 nm. Pump energy density thresholds as low as 3 (mu) J/cm<SUP>2</SUP> and ASE-line halfwidths approximately 10 nm have been observed. Comparable to the typical redox behavior of free TPD molecule the novel TPD- based polymers exhibit fully reversible electron transfer at low potential (E<SUP>Ox</SUP> approximately 0.65 V), which is favorable for hole injection and stable charge transport in the semiconducting organic materials. In addition, these high-Tg polymers can act as the electro-active materials in LEDs, photovoltaic cells and photorefractive devices. The waveguiding properties of Poly-TPD-DPX were determined in planar and strip waveguides to be 12 dB/cm at 640 nm, and 2 dB/cm at 1550 nm.