Tricyclic arylamine containing polymers and electronic devices therefrom

1. A composition comprising a polymer having a repeat unit of the formula:

and additional optional repeat units of the formula

wherein R 1 is independently, in each occurrence H, C 1-40 hydrocarbyl or C 3-40 hydrocarbyl containing one or more S, N, O, P or Si atoms, or both of R 1 together with the 9-carbon on the fluorene may form a C 5-20 ring structure containing one or more S, N, or O atoms;

R 2 is independently in each occurrence C 1-20 hydrocarbyl, C 1-20 hydrocarbyloxy, thioether, C 1-20 hydrocarbyloxycarbonyl, C 1-20 hydrocarbylcarbonyloxy, or cyano;

a is independently, in each occurrence 0 or 1;

X is O, S, SO 2 , C(R 3 ) 2 or N—R 3 wherein R 3 is aryl of C 6 to C 40 or substituted aryl of C 6 to C 40 , aralkyl of C 6 to C 24 , or alkyl of C 1 to C 24 .

Ar is an aryl or heteroaryl group of C 6 to C 40 or substituted aryl or heteroaryl group of C 6 to C 40 ; and Y and Z are independently in each occurrence selected from the group of conjugated unit of the formulas:

wherein the conjugated units may bear substituents, such substituents being independently in each occurrence C 1-20 hydrocarbyl, C 1-20 hydrocarboxyloxy, C 1-20 thioether, C 1-20 hydrocarbyloxycarbonyl, C 1-20 hydrocarboxy carbonyloxy cyano, or fluoro group;

X 1 is O or S;

Q is R or Ar;

R is C 1 to C 20 ;

Ar is an aryl or heteroaryl group of C 6 to C 40 or substituted aryl or heteroaryl group of C 6 to C 40 ; R 4 is independently, in each occurrence H, C 1-40 hydrocarbyl or C 3-40 hydrocarbyl containing one or more S, N, O, P or Si atoms, or both of R 4 together with the 9-carbon on the fluorene may form a C 5-20 ring structure containing one or more S, N, or O atoms and R 5 is independently in each occurrence C 1-20 hydrocarbyl, C 1-20 hydrocarbyl, C 1-20 hydrocarbyloxy, thioether, C 1-20 hydrocarbyloxycarbonyl, C 1-20 hydrocarbylcarbonloxy, or cyano.

2. The composition of claim 1 further comprising a solvent.

3. A film comprising the composition of claim 2 .

4. The composition of claim 1 blended with at least one additional conjugated polymer.

5. The composition of claim 1 wherein the composition emits light in the blue range of the spectrum.

6. The composition of claim 1 wherein the composition emits light in the red range of the spectrum.

7. The composition of claim 1 wherein the composition emits light in the yellow range of the spectrum.

8. The composition of claim 1 wherein the composition emits light in the green range of the spectrum.

9. The composition of claim 1 wherein the composition emits white light.

10. The blue emitting composition of claim 5 wherein R 1 is hexyl or biphenyl, X is S or O, Ar is 4-n-butylphenyl and Z has the formula:

11. The composition of claim 10 wherein Ar is (9,9-dibutyl)-2-fluorenyl.

12. The blue emitting composition of claim 5 wherein R 1 is octyl or 4-hexyloxyphenyl, a is 0; X is O, Ar is 4-n-butylphenyl.

13. The red emitting composition of claim 6 wherein R 1 is C 8 H 17 , X is S, Ar is n-butylphenyl, Y is in at least one occurrence benzothiadiazole and Z is in at least one occurrence dithiophenebenzothiadiazole.

14. The yellow emitting composition of claim 7 wherein R 1 is C 6 H 5 or C 8 H 17 , Ar is 4-n-butylphenyl, a is 0, X is S, and Y is benzothiadiazole.

15. The green emitting composition of claim 8 wherein R 1 is hexyl or octyl, X is S, Ar is n-butylphenyl, a is 0 and Y is benzothiadiazole.

16. The white emitting composition of claim 9 wherein R 1 is C 8 H 17 , X is O, a is 0 and Y is at least in one occurrence benzothiadiazole, bisthienylbenzothiadiazole and a triarylamine with the structure:

17. The white emitting composition of claim 9 wherein R 1 is C 8 H 17 , X is S, a is 0 and Y is bisthienylbenzothiadiazole.

18. An electroluminescent device comprising at least one organic film comprising the composition of claim 1 , arranged between an anode material and a cathode material such that under an applied voltage, the organic film emits visible light which is transmitted through a transparent exterior portion of the device.

19. The device of claim 18 with a turn-on voltage of 20 volts or less.

20. A field effect transistor comprising:

(a) an insulator layer, the insulator layer being an electrical insulator, the insulator layer having a first side and a second side;

(b) a gate, the gate being an electrical conductor, the gate being positioned adjacent the first side of the insulator layer;

(c) a semiconductor layer, the semiconductor layer comprising the composition of claim 1 and a second electrode;

(d) a source, the source being an electrical conductor, the source being in electrical contact with the first end of the semiconductor layer; and

(e) a drain, the drain being an electrical conductor, the drain being in electrical contact with the second end of the semiconductor layer.

21. A photocell comprising a first electrode, a film comprising the polymer of claim 1 and a second electrode.

22. An optoelectronically active polymer which is the reaction product of a mixture comprising a diboronate fluorene monomer, a dihalogenated tricyclic amine monomer and optionally a conjugated monomer.

23. A composition of the formula

wherein X is O, S, SO 2 , C(R 3 ) 2 or N—R 3 wherein R 3 is aryl of C 6 to C 40 or substituted aryl of C 6 to C 40 , aralkyl of C 6 to C 24 , or alkyl of C 1 to C 24 . and Ar is a heteroaryl group or a substituted heteroaryl group of C 6 to C 40 or is selected from the group consisting of 4-n-butylphenyl, 2-fluorenyl, anthracenyl, phenanthrenyl, and pyrenyl; and Hal is a halogen.

24. The composition of claim 23 wherein Hal is Br.