Telluropyrylium electron accepting dye sensitizers for electron donating photoconductive compositions
AssigneeEastman Kodak Company
InventorsMichael R. Detty, Bruce J. Murray, Jerome H. Perlstein
Life of this patent
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Abstract
Novel telluropyrylium dyes are disclosed. The dyes are useful as electron accepting sensitizers for electron donating photoconductive compositions. Novel methods making the dyes are also disclosed.
Claims15
A dye comprising a telluropyrylium nucleus.
A dye comprising a telluropyrylium nucleus having a structure ##STR54## wherein R.sub.1, R.sub.3 and R.sub.5 each independently represent hydrogen, alkyl, alkylamino, dialkylamino, alkoxy, aryloxy, alkylaryl, aryl, heterocyclyl,
- --CH.dbd.CH).sub.n CH.dbd.A.sub.1, --CH.dbd.CH).sub.n A.sub.2
- or a zwitterionic diketonate of the structure:
- ##STR55## wherein R.sub.2 and R.sub.4 each independently represents hydrogen, aryl or alkyl;
- or
- R.sub.2 and R.sub.3, or R.sub.4 and R.sub.5, taken together with the carbon atoms to which they are attached, form a mono- or polynuclear fused carbocyclic ring having from about 5 to 20 carbon atoms;
- R.sub.6 and R.sub.7 each independently represents hydrogen, alkyl, aryl, heteroaryl or a mono- or polycyclic heterocyclylidene group, or R.sub.6 and R.sub.7 taken together with the carbon atoms to which they are attached, form a fused mono- or polycyclic, carbocyclic or heterocyclic group having from about 5 to 20 carbon atoms;
- A.sub.1 represents a mono- or polycyclic heterocyclylidene group;
- A.sub.2 represents hydrogen, alkyl, alkoxy, aryl, amino, dialkylaminoaryl, alkylamino, arylamino, dialkylamino, diarylamino or a mono- or polycyclic heterocyclyl group;
- n represents a number from 0 to 5;
- m represents 1, except when R.sub.1, R.sub.3 or R.sub.5 is the zwitterionic group, m represents 0;
- X represents an anion;
- Y represents BF.sub.2 or PF.sub.4 ;
- and
- Z represents O or S.
A dye comprising a benzotelluropyrylium nucleus.
A dye comprising a benzotelluropyrylium nucleus having a structure:
- ##STR56## wherein, R.sub.10 and R.sub.8 each independently represents hydrogen, alkyl, alkylamino, arylamino, alkoxy, aryloxy, dialkylamino, diarylamino,
- --CH.dbd.CH).sub.n CH.dbd.A.sub.1, --CH.dbd.CH).sub.n A.sub.2
- or a zwitterionic diketonate of the structure:
- ##STR57## A.sub.1 represents a mono- or polycyclic heterocyclylidene group;
- A.sub.2 represents hydrogen, alkyl, alkoxy, aryl, dialkylaminoaryl, dialkylamino, alkylamino, arylamino or a mono- or polycyclic heterocyclyl group;
- R.sub.6 and R.sub.7 each independently represents hydrogen, alkyl, aryl, heteroaryl, a mono- or polycyclic heterocyclylidene group or R.sub.6 and R taken together with the carbon atom to which they are attached, form a fused mono- or polycyclic carbocyclic or heterocyclic group having from about 5 to 20 carbon atoms;
- R.sub.9, R.sub.11, R.sub.12, R.sub.13 and R each independently represents hydrogen, alkyl, alkoxy, aryl, halogen, alkylamino or arylamino;
- or
- R.sub.11 and R.sub.12, R.sub.12 and R.sub.13 or R.sub.13 and R.sub.14, taken together with the carbon atoms to which they are attached, form a fused carbocyclic ring having from 5 to 20 carbon atoms;
- n represents 0, 1 or 2;
- m represents 1 except when R.sub.8 or R.sub.10 is the zwitterionic group, m represents 0;
- X represents an anion;
- Y represents BF.sub.2 or PF.sub.4 ;
- and
- Z represents O or S.
A dye comprising a telluropyrylium nucleus selected from the group consisting of:
- ##STR58## wherein A.sub.1, A.sub.2, n, R.sub.3, R.sub.5 and X for each dye is as defined below:
- ______________________________________ Dye A.sub.1 or No. A.sub.2 R.sub.3 R.sub.5 n X.sup.- ______________________________________ 1 p-Me.sub.2 N C.sub.6 H.sub.4 C.sub.6 H.sub.5 C.sub.6 H.sub.5 0 ClO.sub.4 2 p-Me.sub.2 N C.sub.6 H.sub.4 C.sub.6 H.sub.5 C.sub.6 H.sub.5 0 BF.sub.4 3 p-Me.sub.2 N C.sub.6 H.sub.4 C.sub.6 H.sub.5 C.sub.6 H.sub.5 0 CF.sub.3 SO.sub.3 ##STR59## C.sub.6 H.sub.5 C.sub.6 H.sub.5 1 BF.sub.4 5 ##STR60## C.sub.6 H.sub.5 C.sub.6 H.sub.5 1 ClO.sub.4 6 ##STR61## C.sub.6 H.sub.5 C.sub.6 H.sub.5 1 ClO.sub.4 7 CH.sub.3 CH.sub.2 O C.sub.6 H.sub.5 C.sub.6 H.sub.5 0 FSO.sub.3 8 CH.sub.3 C.sub.6 H.sub.5 C.sub.6 H.sub.5 0 BF.sub.4 9 ##STR62## C.sub.6 H.sub.5 C.sub.6 H.sub.5 1 BF.sub.4 10 ##STR63## C.sub.6 H.sub.5 C.sub.6 H.sub.5 0 BF.sub.4 11 ##STR64## C.sub.6 H.sub.5 C.sub.6 H.sub.5 0 ClO.sub.4 12 ##STR65## C.sub.6 H.sub.5 C.sub.6 H.sub.5 0 ClO.sub.4 13 ##STR66## C.sub.6 H.sub.5 C.sub.6 H.sub.5 0 BF.sub.4 14 p-Me.sub.2 N C.sub.6 H.sub.4 C.sub.6 H.sub.5 C.sub.6 H.sub.5 1 BF.sub.4 15 p-Me.sub. 2 N C.sub.6 H.sub.4 C.sub.6 H.sub.5 C.sub.6 H.sub.5 2 BF.sub.4 16 ##STR67## C.sub.6 H.sub.5 C.sub.6 H.sub.5 1 CF.sub.3 SO.sub.3 17 ##STR68## C.sub.6 H.sub.5 C.sub.6 H.sub.5 1 CF.sub.3 SO.sub.3 18 CH.sub.3 C.sub.6 H.sub.5 C.sub.6 H.sub.5 0 BF.sub.4 19 CH.sub.3 CH.sub.2 O C.sub.6 H.sub.5 C.sub.6 H.sub.5 0 FSO.sub.3 20 p-Me.sub.2 N C.sub.6 H.sub.4 CH.sub.3 CH.sub.3 0 BF.sub.4 ______________________________________
A dye comprising a benzotelluropyrylium nucleus selected from the group of dyes consisting of:
- ##STR69## wherein A, n, R.sub.3, R.sub.8, R.sub.13 and X for each dye is as defined below:
- ______________________________________ Dye A.sub.1 or No. A.sub.2 R.sub.3 R.sub.13 n X.sup.- ______________________________________ 1 H C.sub.6 H.sub.5 CH.sub.3 O 0 ClO.sub.4 2 H C.sub.6 H.sub.5 CH.sub.3 O 0 PF.sub.6 3 CH.sub.3 C.sub.6 H.sub.5 CH.sub.3 O 0 CF.sub.3 SO.sub.3 4 CH.sub.3 C.sub.6 H.sub.5 CH.sub.3 O 0 BF.sub.4 5 CH.sub.3 C.sub.6 H.sub.5 CH.sub.3 O 0 ClO.sub.4 6 CH.sub.3 C.sub.6 H.sub.5 CH.sub.3 O 0 ClO.sub.4 7 CH.sub.3 CH.sub.2 O C.sub.6 H.sub.5 CH.sub.3 O 0 FSO.sub.3 8 CH.sub.3 CH.sub.2 O CH.sub.3 CH.sub.3 O 0 FSO.sub.3 9 p-Me.sub.2 N C.sub.6 H.sub.4 C.sub.6 H.sub.5 CH.sub.3 O 0 BF.sub.4 10 p-Me.sub.2 N C.sub.6 H.sub.4 C.sub.6 H.sub.5 CH.sub.3 O 0 ClO.sub.4 11 p-Me.sub.2 N C.sub. 6 H.sub.4 C.sub.6 H.sub.5 CH.sub.3 O 1 CF.sub.3 SO.sub.3 12 p-Me.sub.2 N C.sub.6 H.sub.4 C.sub.6 H.sub.5 CH.sub.3 O 1 BF.sub.4 13 p-Me.sub.2 N C.sub.6 H.sub.4 C.sub.6 H.sub.5 CH.sub.3 O 2 CF.sub.3 SO.sub.3 14 Me.sub.2 N C.sub.6 H.sub.5 CH.sub.3 O 1 CF.sub.3 SO.sub.3 15 ##STR70## C.sub.6 H.sub.5 CH.sub.3 O 0 BF.sub.4 16 ##STR71## C.sub.6 H.sub.5 CH.sub.3 O 0 ClO.sub.4 17 ##STR72## C.sub.6 H.sub.5 CH.sub.3 O 0 ClO.sub.4 18 ##STR73## C.sub.6 H.sub.5 CH.sub.3 O 1 CF.sub.3 SO.sub.3 19 ##STR74## C.sub.6 H.sub.5 CH.sub.3 O 1 ClO.sub.4 20 ##STR75## C.sub.6 H.sub.5 CH.sub.3 O 1 PF.sub.6 21 ##STR76## C.sub.6 H.sub.5 CH.sub.3 O 1 CF.sub.3 SO.sub.3 22 ##STR77## C.sub.6 H.sub.5 CH.sub.3 O 2 PF.sub.6 23 ##STR78## C.sub.6 H.sub.5 CH.sub.3 O 2 CF.sub.3 SO.sub.3 24 ##STR79## C.sub.6 H.sub.5 CH.sub. 3 O 3 CF.sub.3 SO.sub.3 25 ##STR80## C.sub.6 H.sub.5 CH.sub.3 O 1 CF.sub.3 SO.sub.3 26 ##STR81## C.sub.6 H.sub.5 CH.sub.3 O 2 CF.sub.3 SO.sub.3 27 ##STR82## C.sub.6 H.sub.5 CH.sub.3 O 1 BF.sub.4 28 ##STR83## C.sub.6 H.sub.5 CH.sub.3 O 1 BF.sub.4 29 ##STR84## C.sub.6 H.sub.5 CH.sub.3 O 1 PF.sub.6 30 C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 O 0 CF.sub.3 SO.sub.3 ______________________________________
A dye comprising a telluropyrylium nucleus and zwitterionic diketonate substituent selected from the group of dyes consisting of:
- ##STR85##
Dependencies are inferred from the claim text.