Electroluminescent polymers and use thereof in light-emitting devices

In a conductive composition comprised of a doped conjugated polymer, the improvement comprising employing a polymer or copolymer comprised of monomer units having the structure of formula (I):

• wherein:
• Ar1 and Ar2 are independently selected from the group consisting of monocyclic, bicyclic and polycyclic arylene, heteroarylene, substituted arylene and substituted heteroarylene;
• L is alkylene, alkenylene, substituted alkylene, substituted alkenylene, heteroalkylene, heteroalkenylene, substituted heteroalkylene, substituted heteroalkenylene, arylene, heteroarylene, substituted arylene, substituted heteroarylene, or a combination thereof;
• Q is a heteroatom;
• m is zero or 1;
• p is zero or 1, and q is zero or 1, with the proviso that when p is zero, then q is zero;
• x is zero or 1;
• Q1 and Q2 are independently selected from the group consisting of H, aryl, heteroaryl, substituted aryl, substituted heteroaryl, alkyl, substituted alkyl, heteroalkyl, and substituted heteroalkyl, and Q3 is selected from the group consisting of alkyl, substituted alkyl, heteroalkyl, and substituted heteroalkyl, with the proviso that when m is 1, Q1 and Q2 are other than H;
• and
• A− is a negatively charged counterion.

In a field effect transistor comprising a gate electrode, a source electrode, a drain electrode and a channel electrically connecting the source electrode and the drain electrode, the improvement which comprises employing a channel comprising a polymer or copolymer comprised of monomer units having the structure of formula (I):

• wherein:
• Ar1 and Ar2 are independently selected from the group consisting of monocyclic, bicyclic and polycyclic arylene, heteroarylene, substituted arylene and substituted heteroarylene;
• L is alkylene, alkenylene, substituted alkylene, substituted alkenylene, heteroalkylene, heteroalkenylene, substituted heteroalkylene, substituted heteroalkenylene, arylene, heteroarylene, substituted arylene, substituted heteroarylene, or a combination thereof;
• Q is a heteroatom;
• m is zero or 1;
• p is zero or 1, and q is zero or 1, with the proviso that when p is zero, then q is zero;
• x is zero or 1;
• Q1 and Q2 are independently selected from the group consisting of H, aryl, heteroaryl, substituted aryl, substituted heteroaryl, alkyl, substituted alkyl, heteroalkyl, and substituted heteroalkyl, and Q3 is selected from the group consisting of alkyl, substituted alkyl, heteroalkyl, and substituted heteroalkyl, with the proviso that when m is 1, Q1 and Q2 are other than H;
• and
• A− is a negatively charged counterion.

In a photodetector device comprised of a semiconductive layer disposed between first and second electrodes, and a means for detecting a photocurrent flowing between the electrodes, the improvement which comprises employing a semiconductive layer comprised of a polymer or copolymer comprised of monomer units having the structure of formula (I):

• wherein:
• Ar1 and Ar2 are independently selected from the group consisting of monocyclic, bicyclic and polycyclic arylene, heteroarylene, substituted arylene and substituted heteroarylene;
• L is alkylene, alkenylene, substituted alkylene, substituted alkenylene, heteroalkylene, heteroalkenylene, substituted heteroalkylene, substituted heteroalkenylene, arylene, heteroarylene, substituted arylene, substituted heteroarylene, or a combination thereof;
• Q is a heteroatom;
• m is zero or 1;
• p is zero or 1, and q is zero or 1, with the proviso that when p is zero, then q is zero;
• x is zero or 1;
• Q1 and Q2 are independently selected from the group consisting of H, aryl, heteroaryl, substituted aryl, substituted heteroaryl, alkyl, substituted alkyl, heteroalkyl, and substituted heteroalkyl, and Q3 is selected from the group consisting of alkyl, substituted alkyl, heteroalkyl, and substituted heteroalkyl, with the proviso that when m is 1, Q1 and Q2 are other than H;
• and
• A− is a negatively charged counterion.

In a photovoltaic device useful for the generation of electrical power comprised of a first electrode, a semiconductive layer provided on the first electrode, and a second electrode provided on the light incidence surface of the semiconductive layer, the improvement which comprises employing a semiconductive layer comprised of the a polymer or copolymer comprised of monomer units having the structure of formula (I):

• wherein:
• Ar1 and Ar2 are independently selected from the group consisting of monocyclic, bicyclic and polycyclic arylene, heteroarylene, substituted arylene and substituted heteroarylene;
• L is alkylene, alkenylene, substituted alkylene, substituted alkenylene, heteroalkylene, heteroalkenylene, substituted heteroalkylene, substituted heteroalkenylene, arylene, heteroarylene, substituted arylene, substituted heteroarylene, or a combination thereof;
• Q is a heteroatom;
• m is zero or 1;
• p is zero or 1, and q is zero or 1, with the proviso that when p is zero, then q is zero;
• x is zero or 1;
• Q1 and Q2 are independently selected from the group consisting of H, aryl, heteroaryl, substituted aryl, substituted heteroaryl, alkyl, substituted alkyl, heteroalkyl, and substituted heteroalkyl, and Q3 is selected from the group consisting of alkyl, substituted alkyl, heteroalkyl, and substituted heteroalkyl, with the proviso that when m is 1, Q1 and Q2 are other than H;
• and
• A− is a negatively charged counterion.

In a light-emitting electrochemical cell comprised of a conductive transparent or semitransparent substrate, a thin film or a conjugated polymer and an ionizable species deposited on the substrate, and an electrode deposited on the thin film, the improvement which comprises employing a polymer or copolymer comprised of monomer units having the structure of formula (I):

• wherein:
• Ar1 and Ar2 are independently selected from the group consisting of monocyclic, bicyclic and polycyclic arylene, heteroarylene, substituted arylene and substituted heteroarylene;
• L is alkylene, alkenylene, substituted alkylene, substituted alkenylene, heteroalkylene, heteroalkenylene, substituted heteroalkylene, substituted heteroalkenylene, arylene, heteroarylene, substituted arylene, substituted heteroarylene, or a combination thereof;
• Q is a heteroatom;
• m is zero or 1;
• p is zero or 1, and q is zero or 1, with the proviso that when p is zero, then q is zero;
• x is zero or 1;
• Q1 and Q2 are independently selected from the group consisting of H, aryl, heteroaryl, substituted aryl, substituted heteroaryl, alkyl, substituted alkyl, heteroalkyl, and substituted heteroalkyl, and Q3 is selected from the group consisting of alkyl, substituted alkyl, heteroalkyl, and substituted heteroalkyl, with the proviso that when m is 1, Q1 and Q2 are other than H;
• and
• A− is a negatively charged counterion.

In an electrochemical sensor comprising a counter electrode, a working electrode, and a means for applying or measuring an electrical potential between the working and counter electrodes, the improvement which comprises employing a polymer or copolymer comprised of monomer units having the structure of formula (I):

• wherein:
• Ar1 and Ar2 are independently selected from the group consisting of monocyclic, bicyclic and polycyclic arylene, heteroarylene, substituted arylene and substituted heteroarylene;
• L is alkylene, alkenylene, substituted alkylene, substituted alkenylene, heteroalkylene, heteroalkenylene, substituted heteroalkylene, substituted heteroalkenylene, arylene, heteroarylene, substituted arylene, substituted heteroarylene, or a combination thereof;
• Q is a heteroatom;
• m is zero or 1;
• p is zero or 1, and q is zero or 1, with the proviso that when p is zero, then q is zero;
• x is zero or 1;
• Q1 and Q2 are independently selected from the group consisting of H, aryl, heteroaryl, substituted aryl, substituted heteroaryl, alkyl, substituted alkyl, heteroalkyl, and substituted heteroalkyl, and Q3 is selected from the group consisting of alkyl, substituted alkyl, heteroalkyl, and substituted heteroalkyl, with the proviso that when m is 1, Q1 and Q2 are other than H;
• and
• A− is a negatively charged counterion.

A cavity emission electroluminescent device, comprising:

• a hole-injection electrode layer;
• an electron-injection electrode layer;
• a dielectric layer interposed between the hole-injecting and electron-injecting electrode layers;
• and
• a cavity extending through at least the dielectric layer and one of the electrode layers and having an interior cavity surface comprising a hole-injection electrode region, and an electron-injection electrode region and a dielectric region,
• wherein an electroluminescent coating material comprising a polymer or copolymer is in electrical contact with the hole-injection and electron-injection regions of the interior cavity surface,
• and wherein said polymer or copolymer is comprised of monomer units having the structure of formula (I):
• wherein:
• Ar1 and Ar2 are independently selected from the group consisting of monocyclic, bicyclic and polycyclic arylene, heteroarylene, substituted arylene and substituted heteroarylene;
• L is alkylene, alkenylene, substituted alkylene, substituted alkenylene, heteroalkylene, heteroalkenylene, substituted heteroalkylene, substituted heteroalkenylene, arylene, heteroarylene, substituted arylene, substituted heteroarylene, or a combination thereof;
• Q is a heteroatom;
• m is zero or 1;
• p is zero or 1, and q is zero or 1, with the proviso that when p is zero, then q is zero;
• x is zero or 1;
• Q1 and Q2 are independently selected from the group consisting of H, aryl, heteroaryl, substituted aryl, substituted heteroaryl, alkyl, substituted alkyl, heteroalkyl, and substituted heteroalkyl, and Q3 is selected from the group consisting of alkyl, substituted alkyl, heteroalkyl, and substituted heteroalkyl, with the proviso that when m is 1, Q1 and Q2 are other than H;
• and
• A− is a negatively charged counterion.