US2013247989A1PendingUtilityA1
Inert solution-processable molecular chromophores for organic electronic devices
Est. expiryMar 23, 2032(~5.7 yrs left)· nominal 20-yr term from priority
C07D 519/00C07F 7/0816B82Y 10/00C07D 495/04H10K 30/50H10K 85/657Y02E10/549H10K 85/655H10K 85/40H10K 85/215H10K 30/00H10K 30/30Y02P70/50H01L 51/0071H01L 51/42
60
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Claims
Abstract
Small organic molecule chromophores containing a benzo[c][1,2,5]thiadiazole with an electron-withdrawing substituent W in the 5-position (5BTH), benzo[c][1,2,5]oxadiazole with an electron-withdrawing substituent W in the 5-position (5BO), 2H-benzo[d][1,2,3]triazole (5BTR) with an electron-withdrawing substituent W in the 5-position (5BTR), 5-fluorobenzo[c][1,2,5]thiadiazole (FBTH), 5-fluorobenzo[c][1,2,5]oxadiazole (FBO), or 5-fluoro-2H-benzo[d][1,2,3]triazole (FBTR) core structure are disclosed. Such compounds can be used in organic heterojunction devices, such as organic small molecule solar cells and transistors.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . An electronic or optoelectronic device comprising a non-polymeric compound, said compound incorporating one or more groups of Formula A:
where said non-polymeric compound is used in an active layer of the electronic or optoelectronic device;
where M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where either X 1 is CH and Y 1 is —C(W)—, or X 1 is —C(W)— and Y 1 is CH; and
W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F.
2 . The electronic or optoelectronic device according to claim 1 ,
wherein the non-polymeric compound is used in an active layer of said device.
3 . The electronic or optoelectronic device according to claim 1 ,
wherein said device is a solar cell.
4 . The electronic or optoelectronic device according to claim 1 ,
wherein M is sulfur and W is F.
5 . The electronic or optoelectronic device according to claim 1 ,
wherein the active layer comprises a compound of Formula II:
where X 1 and Y 1 are selected from —C(W)— and CH, where when X 1 is —C(W)—, Y 1 is CH, and when X 1 is CH, Y 1 is —C(W)—; and where, independently of X 1 and Y 1 , X 2 and Y 2 are selected from —C(W)— and CH, where when X 2 is —C(W)—, Y 2 is CH, and when X 2 is CH, Y 2 is —C(W)—;
W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F;
M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
n is an integer between 0 and 5, inclusive;
A 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups;
each B 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups; and
each B 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
6 . The electronic or optoelectronic device according to claim 5 , wherein the active layer comprises a compound of Formula IIa-F, Formula IIb-F, or Formula IIc-F:
where M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F;
where A 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups;
B 1 is independently selected from a C 6 -C 30 substituted or unsubstituted aryl or heteroaryl group;
each B 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a C 6 -C 30 substituted or unsubstituted aryl or heteroaryl group; and
n is an integer between 0 and 5 inclusive.
7 . The electronic or optoelectronic device according to claim 6 , wherein A 1 is independently selected from substituted or unsubstituted thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole, benzimidazole, benzofuran, isobenzofuran, thiadiazole, dithienopyrrole, dithienophosphole and carbazole 9,9-RR′-9H-fluorene, 9-R-9H-carbazole, 3,3′-RR′silylene-2,2′-bithiophene, 3,3′RR′-cyclopenta[2,1-b:3,4-b′]-dithiophene, where R and R′═C 1 -C 30 alkyl or C 6 -C 30 aryl.
8 . The electronic or optoelectronic device according to claim 6 , wherein B 1 is independently selected from substituted or unsubstituted thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole, benzimidazole, benzofuran, isobenzofuran, thiadiazole, perfluorylbenzene, and carbazole.
9 . The electronic or optoelectronic device according to claim 1 , wherein the active layer comprises a compound of Formula I:
wherein X 1 and Y 1 are selected from —C(W)— and CH, where when X 1 is —C(W)—, Y 1 is CH, and when X 1 is CH, Y 1 is —C(W)—; and
where M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where, independently of X 1 and Y 1 , X 2 and Y 2 are selected from —C(W)— and CH, where when X 2 is —C(W)—, Y 2 is CH, and when X 2 is CH, Y 2 is —C(W)—;
where W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F;
A 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups;
each B 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups; and
each B 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a C 6 -C 30 substituted or unsubstituted aryl or heteroaryl group.
10 . The electronic or optoelectronic device according to claim 9 , wherein A 1 is independently selected from substituted or unsubstituted thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole, benzimidazole, benzofuran, isobenzofuran, thiadiazole, dithienopyrrole, dithienophosphole, and carbazole 9,9-RR′-9H-fluorene, 9-R-9H-carbazole, 3,3′-RR′silylene-2,2′-bithiophene, 3,3′RR′-cyclopenta[2,1-b:3,4-b′]-dithiophene where R and R′═C 1 -C 30 alkyl or C 6 -C 30 aryl.
11 . The electronic or optoelectronic device according to claim 9 , wherein each B 1 is selected from substituted or unsubstituted thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole, benzimidazole, benzofuran, isobenzofuran, thiadiazole, perfluorylbenzene, and carbazole.
12 . The electronic or optoelectronic device according to claim 9 , wherein the compound of Formula I is selected from formulas Ia-F, Ib-F, or Ic-F:
13 . The electronic or optoelectronic device according to claim 1 , wherein the active layer comprises a compound of Formula III-F:
where M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where H 1 is selected from A 1 , —B 1 —B 2 , -A 1 -B 1 —B 2 , or
n is an integer between 0 and 5, inclusive;
A 1 (when present) is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups;
each B 1 (when present) is independently selected from substituted or unsubstituted aryl or heteroaryl groups; and
each B 2 (when present) is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group.
14 . The electronic or optoelectronic device according to claim 13 , wherein the compound of Formula III-F is selected from a compound of Formula IIIa-F, Formula IIIb-F, Formula IIIc-F, or Formula IIId-F:
15 . The electronic or optoelectronic device according to claim 1 , wherein the active layer comprises a compound of Formula IV-V:
where X 1 and Y 1 are selected from —C(W)— and CH, where when X 1 is —C(W)—, Y 1 is CH, and when X 1 is CH, Y 1 is —C(W)—; and where, independently of X 1 and Y 1 , X 2 and Y 2 are selected from —C(W)— and CH, where when X 2 is —C(W)—, Y 2 is CH, and when X 2 is CH, Y 2 is —C(W)—;
and where, independently of X 1 , Y 1 , X 2 , and Y 2 , X 3 and Y 3 are selected from —C(W)— and CH, where when X 3 is —C(W)—, Y 3 is CH, and when X 3 is CH, Y 3 is —C(W)—;
M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F;
K 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups;
each E 1 is independently either absent, or selected from substituted or unsubstituted aryl or heteroaryl groups;
each D 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups; and
each D 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group.
16 . The electronic or optoelectronic device according to claim 15 , where the compound of Formula IV-V is selected from a compound of Formula IVa-F or Formula IVb-F:
where M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where K 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups;
each D 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups; and
each D 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a C 6 -C 30 substituted or unsubstituted aryl or heteroaryl group.
17 . The electronic or optoelectronic device according to claim 15 , where the compound of Formula IV-V is selected from a compound of Formula Va-F or Formula Vb-F:
where M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where K 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups;
each D 1 and E 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups; and
each D 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a C 6 -C 30 substituted or unsubstituted aryl or heteroaryl group.
18 . The electronic or optoelectronic device according to claim 1 , wherein the active layer comprises a compound of Formula VI-VII:
where the moiety
is selected from
(2,2′,7,7′-yl-9,9′-spirobi[fluorene]),
(3,3′,7,7′-yl-5,5′-spirobi[dibenzo[b,d]silole]),
(2,2′,6,6′-yl-4,4″-spirobi[cyclopenta[1,2-b:5,4-b′]dithiophene]), or
(2,2′,6,6′-yl-4,4′-spirobi[silolo[3,2-b:4,5-b′]dithiophene]);
where X 1 and Y 1 are selected from —C(W)— and CH, where when X 1 is —C(W)—, Y 1 is CH, and when X 1 is CH, Y 1 is —C(W)—; and where, independently of X 1 and Y 1 , X 2 and Y 2 are selected from —C(W)— and CH, where when X 2 is —C(W)—, Y 2 is CH, and when X 2 is CH, Y 2 is —C(W)—;
and where, independently of X 1 , Y 1 , X 2 , and Y 2 , X 3 and Y 3 are selected from —C(W)— and CH, where when X 3 is —C(W)—, Y 3 is CH, and when X 3 is CH, Y 3 is —C(W)—; and where, independently of X 1 , Y 1 , X 2 , Y 2 , X 3 , and Y 3 , X 4 and Y 4 are selected from —C(W)— and CH, where when X 4 is —C(W)—, Y 4 is CH, and when X 4 is CH, Y 4 is —C(W)—;
where M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F;
each F 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups;
each G 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups; and
each G 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group.
19 . The electronic or optoelectronic device according to claim 18 , wherein the compound of Formula VI-VII is selected from a compound of Formula VIa-F or Formula VIb-F:
where M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where each F 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups;
each G 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups; and
each G 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a C 6 -C 30 substituted or unsubstituted aryl or heteroaryl group.
20 . The electronic or optoelectronic device according to claim 18 , wherein the compound of Formula VI-VII is selected from a compound of Formula VIIa-F or Formula VIIb-F:
where M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where each F 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups;
each G 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups; and
each G 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a C 6 -C 30 substituted or unsubstituted aryl or heteroaryl group.
21 . The electronic or optoelectronic device according to claim 1 , wherein the active layer comprises a compound of Formula 1-F, Formula 2-F, Formula 3-F, Formula 4-F, Formula 5-F, Formula 6-F, Formula 7-F, Formula 8-F, Formula 9-F or Formula 10-F:
where:
M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
n is an integer from 0 to 5 inclusive;
m is an integer from 0 to 5 inclusive;
R 2 is selected from H, C 1 -C 16 alkyl, —O—C 1 -C 16 alkyl, C 2 -C 16 alkenyl, and C 2 -C 16 alkynyl;
J is selected from CH and N;
X is S, O, or NH when J is CH; and X is S when J is N;
R 4 is C 6 -C 30 aryl optionally substituted with one or more C 1 -C 16 alkyl groups; R 6 is selected from aryl, perfluoroaryl, or C 6 -C 30 aryl optionally perfluorinated or optionally substituted with one or more C 1 -C 16 alkyl groups; and each DONOR is independently selected from:
where X is C or Si;
A is N or P;
R 11 is selected from C 1 -C 16 alkyl;
R 12 is selected from C 1 -C 16 alkyl, C 6 -C 20 unsubstituted aryl, or C 6 -C 20 aryl substituted with one or more groups selected from —F, C 1 -C 20 alkyl, C 1 -C 20 fluoroalkyl, —O—C 1 -C 20 alkyl, or —C 1 -C 20 fluoroalkyl;
R 13 is selected from C 1 -C 16 alkyl or C 6 -C 20 aryl;
R 14 is selected from C 1 -C 16 alkyl, —O—C 1 -C 16 alkyl, —C(═O)—O—C 1 -C 16 alkyl, or —O—C(═O)—C 1 -C 16 alkyl; and
R 15 is selected from C 1 -C 16 alkyl, C 6 -C 20 unsubstituted aryl, or C 6 -C 20 aryl substituted with one or more groups selected from —F, C 1 -C 20 alkyl, C 1 -C 20 fluoroalkyl, —O—C 1 -C 20 alkyl, or —C 1 -C 20 fluoroalkyl; and
R 16 is selected from C 1 -C 16 alkyl, C 6 -C 20 unsubstituted aryl, or C 6 -C 20 aryl substituted with one or more groups selected from —F, C 1 -C 20 alkyl, C 1 -C 20 fluoroalkyl, —O—C 1 -C 20 alkyl, or —C 1 -C 20 fluoroalkyl;
wherein when only one valence of the DONOR unit is required to bond to the remainder of the molecule, the other valence of the DONOR is terminated by H or C 1 -C 20 alkyl.
22 . The device of claim 5 , wherein said device comprises:
1) a first hole-collecting electrode optionally coated onto a transparent substrate; 2) an optional layer or layers adjacent to the first electrode, such as an electron-blocking, exciton-blocking, or hole-transporting layer; 3) a layer comprising a mixture of an electron acceptor material and an organic non-polymeric electron donor, said electron donor comprising a compound of Formula II; 4) an optional layer or layers such as hole-blocking, exciton-blocking, or electron-transporting layers; and 5) a second electron-collecting electrode.
23 . The device of claim 5 , wherein said device comprises:
1) a first hole-collecting electrode optionally coated onto a transparent substrate; 2) an optional layer or layers adjacent to the first electrode, such as an electron-blocking, exciton-blocking, or hole-transporting layer; 3) a layer comprising a mixture of an organic non-polymeric electron acceptor material and an electron donor, said electron acceptor comprising a compound of Formula II; 4) an optional layer or layers such as hole-blocking, exciton-blocking, or electron-transporting layers; and 5) a second electron-collecting electrode.
24 . A non-polymeric compound, comprising one or more groups of Formula A:
where said non-polymeric compound is used in an electronic or optoelectronic device;
where M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where either X 1 is CH and Y 1 is —C(W)—, or X 1 is —C(W)— and Y 1 is CH; and
W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F.
25 . A compound of claim 24 of the Formula II:
where X 1 and Y 1 are selected from —C(W)— and CH, where when X 1 is —C(W)—, Y 1 is CH, and when X 1 is CH, Y 1 is —C(W)—; and where, independently of X 1 and Y 1 , X 2 and Y 2 are selected from —C(W)— and CH, where when X 2 is —C(W)—, Y 2 is CH, and when X 2 is CH, Y 2 is —C(W)—;
W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F;
M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
n is an integer between 0 and 5, inclusive;
A 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups;
each B 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups; and
each B 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
26 . A compound according to claim 25 of Formula IIa-F, Formula IIb-F, or Formula IIc-F:
where M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F;
where A 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups;
B 1 is independently selected from a C 6 -C 30 substituted or unsubstituted aryl or heteroaryl group;
each B 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a C 6 -C 30 substituted or unsubstituted aryl or heteroaryl group; and
n is an integer between 0 and 5 inclusive.
27 . The compound of claim 26 , wherein A 1 is independently selected from substituted or unsubstituted thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole, benzimidazole, benzofuran, isobenzofuran, thiadiazole, dithienopyrrole, dithienophosphole and carbazole 9,9-RR′-9H-fluorene, 9-R-9H-carbazole, 3,3′-RR′silylene-2,2′-bithiophene, 3,3′RR′-cyclopenta[2,1-b:3,4-b′]-dithiophene, where R and R′═C 1 -C 30 alkyl or C 6 -C 30 aryl.
28 . The compound of claim 26 , wherein B 1 is independently selected from substituted or unsubstituted thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole, benzimidazole, benzofuran, isobenzofuran, thiadiazole, perfluorylbenzene, and carbazole.
29 . A compound of claim 24 of Formula I:
wherein X 1 and Y 1 are selected from —C(W)— and CH, where when X 1 is —C(W)—, Y 1 is CH, and when X 1 is CH, Y 1 is —C(W)—; and
where M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where, independently of X 1 and Y 1 , X 2 and Y 2 are selected from —C(W)— and CH, where when X 2 is —C(W)—, Y 2 is CH, and when X 2 is CH, Y 2 is —C(W)—;
where W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F;
A 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups;
each B 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups; and
each B 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a C 6 -C 30 substituted or unsubstituted aryl or heteroaryl group.
30 . The compound of claim 29 , wherein A 1 is independently selected from substituted or unsubstituted thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole, benzimidazole, benzofuran, isobenzofuran, thiadiazole, dithienopyrrole, dithienophosphole, and carbazole 9,9-RR′-9H-fluorene, 9-R-9H-carbazole, 3,3′-RR′silylene-2,2′-bithiophene, 3,3′RR′-cyclopenta[2,1-b:3,4-b′]-dithiophene where R and R′═C 1 -C 30 alkyl or C 6 -C 30 aryl.
31 . The compound of claim 29 , wherein each B 1 is selected from substituted or unsubstituted thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole, benzimidazole, benzofuran, isobenzofuran, thiadiazole, perfluorylbenzene, and carbazole.
32 . A compound of claim 29 of the following formulas Ia-F, Ib-F, or Ic-F:
33 . A compound of claim 24 of Formula III-F:
where M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where H 1 is selected from A 1 , —B 1 —B 2 , -A 1 -B 1 —B 2 , or
n is an integer between 0 and 5, inclusive;
A 1 (when present) is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups;
each B 1 (when present) is independently selected from substituted or unsubstituted aryl or heteroaryl groups; and
each B 2 (when present) is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group.
34 . A compound of claim 33 of Formula IIIa-F, Formula IIIb-F, Formula IIIc-F, or Formula IIId-F:
35 . A compound of claim 24 of Formula IV-V:
where X 1 and Y 1 are selected from —C(W)— and CH, where when X 1 is —C(W)—, Y 1 is CH, and when X 1 is CH, Y 1 is —C(W)—; and where, independently of X 1 and Y 1 , X 2 and Y 2 are selected from —C(W)— and CH, where when X 2 is —C(W)—, Y 2 is CH, and when X 2 is CH, Y 2 is —C(W)—;
and where, independently of X 1 , Y 1 , X 2 , and Y 2 , X 3 and Y 3 are selected from —C(W)— and CH, where when X 3 is —C(W)—, Y 3 is CH, and when X 3 is CH, Y 3 is —C(W)—;
M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F;
K 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups;
each E 1 is independently either absent, or selected from substituted or unsubstituted aryl or heteroaryl groups;
each D 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups; and
each D 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group.
36 . A compound of claim 35 of Formula IVa-F or Formula IVb-F:
where M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where K 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups;
each D 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups; and
each D 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a C 6 -C 30 substituted or unsubstituted aryl or heteroaryl group.
37 . A compound of claim 35 of Formula Va-F or Formula Vb-F:
where M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where K 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups;
each D 1 and E 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups; and
each D 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a C 6 -C 30 substituted or unsubstituted aryl or heteroaryl group.
38 . A compound of claim 24 of Formula VI-VII:
where the moiety
is selected from
(2,2′,7,7′-yl-9,9′-spirobi[fluorene]),
(3,3′,7,7′-yl-5,5′-spirobi[dibenzo[b,d]silole]),
(2,2′,6,6′-yl-4,4″-spirobi[cyclopenta[1,2-b:5,4-b′]dithiophene]), or
(2,2′,6,6′-yl-4,4′-spirobi[silolo[3,2-b:4,5-b′]dithiophene]);
where X 1 and Y 1 are selected from —C(W)— and CH, where when X 1 is —C(W)—, Y 1 is CH, and when X 1 is CH, Y 1 is —C(W)—; and where, independently of X 1 and Y 1 , X 2 and Y 2 are selected from —C(W)— and CH, where when X 2 is —C(W)—, Y 2 is CH, and when X 2 is CH, Y 2 is —C(W)—;
and where, independently of X 1 , Y 1 , X 2 , and Y 2 , X 3 and Y 3 are selected from —C(W)— and CH, where when X 3 is —C(W)—, Y 3 is CH, and when X 3 is CH, Y 3 is —C(W)—; and where, independently of X 1 , Y 1 , X 2 , Y 2 , X 3 , and Y 3 , X 4 and Y 4 are selected from —C(W)— and CH, where when X 4 is —C(W)—, Y 4 is CH, and when X 4 is CH, Y 4 is —C(W)—;
where M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F;
each F 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups;
each G 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups; and
each G 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group.
39 . A compound of claim 38 of Formula VIa-F or Formula VIb-F:
where M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where each F 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups;
each G 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups; and
each G 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a C 6 -C 30 substituted or unsubstituted aryl or heteroaryl group.
40 . A compound of claim 38 of Formula VIIa-F or Formula VIIb-F:
where M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
where each F 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups;
each G 1 is independently selected from C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups; and
each G 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a C 6 -C 30 substituted or unsubstituted aryl or heteroaryl group.
41 . A compound of claim 24 selected from Formula 1-F, Formula 2-F, Formula 3-F, Formula 4-F, Formula 5-F, Formula 6-F, Formula 7-F, Formula 8-F, Formula 9-F or Formula 10-F:
where:
M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
n is an integer from 0 to 5 inclusive;
m is an integer from 0 to 5 inclusive;
R 2 is selected from H, C 1 -C 16 alkyl, —O—C 1 -C 16 alkyl, C 2 -C 16 alkenyl, and C 2 -C 16 alkynyl;
J is selected from CH and N;
X is S, O, or NH when J is CH; and X is S when J is N;
R 4 is C 6 -C 30 aryl optionally substituted with one or more C 1 -C 16 alkyl groups; R 6 is selected from aryl, perfluoroaryl, or C 6 -C 30 aryl optionally perfluorinated or optionally substituted with one or more C 1 -C 16 alkyl groups; and each DONOR is independently selected from:
where X is C or Si;
A is N or P;
R 11 is selected from C 1 -C 16 alkyl;
R 12 is selected from C 1 -C 16 alkyl, C 6 -C 20 unsubstituted aryl, or C 6 -C 20 aryl substituted with one or more groups selected from —F, C 1 -C 20 alkyl, C 1 -C 20 fluoroalkyl, —O—C 1 -C 20 alkyl, or —C 1 -C 20 fluoroalkyl;
R 13 is selected from C 1 -C 16 alkyl or C 6 -C 20 aryl;
R 14 is selected from C 1 -C 16 alkyl, —O—C 1 -C 16 alkyl, —C(═O)—O—C 1 -C 16 alkyl, or —O—C(═O)—C 1 -C 16 alkyl; and
R 15 is selected from C 1 -C 16 alkyl, C 6 -C 20 unsubstituted aryl, or C 6 -C 20 aryl substituted with one or more groups selected from —F, C 1 -C 20 alkyl, C 1 -C 20 fluoroalkyl, —O—C 1 -C 20 alkyl, or —C 1 -C 20 fluoroalkyl; and
R 16 is selected from C 1 -C 16 alkyl, C 6 -C 20 unsubstituted aryl, or C 6 -C 20 aryl substituted with one or more groups selected from —F, C 1 -C 20 alkyl, C 1 -C 20 fluoroalkyl, —O—C 1 -C 20 alkyl, or —C 1 -C 20 fluoroalkyl;
wherein when only one valence of the DONOR unit is required to bond to the remainder of the molecule, the other valence of the DONOR is terminated by H or C 1 -C 20 alkyl.Join the waitlist — get patent alerts
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