US 2024/0247004 A1Published application

New cerium (iv) complexes and their use in organic electronics

OwnerSascha Dorok, Marcus Papmeyer +1inventors

InventorsSascha Dorok, Marcus Papmeyer, Leonard Eymann

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Abstract

The present invention relates to new cerium (IV) complexes. Further, the present invention relates to electronically doped semiconductor materials and an electronic component comprising cerium (IV) complexes. A further object of the invention is the use of the cerium (IV) complexes as electron acceptors, especially as p-dopants and electron transport materials in organic electronic components.

Claims15

Dependent claims

Compound of the general formula (I)

wherein
L1;
L2;
L3;
and L4 are independently from each other selected from a bidentate ligand having the general formula (II)
wherein
Y represents N or CR3;
R1 represents CFRaRb, t-butyl, adamantyl, C2F5, n-C3F7, C3-C7-cycloalkyl, phenyl, naphthyl, pyridyl, pyrimidyl, triazinyl, wherein cycloalkyl is unsubstituted or substituted with 1 to 13 radicals selected from fluorine and CF3,
phenyl is substituted by at least one radical selected from NO2, F, Cl, Br, CN, CF3, SF5, OCF3, SCF3, SO2CF3, N═C(CF3)2, and N(SO2CF3)2,
naphthyl is unsubstituted or substituted with 1 to 7 radicals selected from CN, NO2, F, Cl, Br, C1-C4-haloalkyl, OCF3, SCF3, SO2CF3, N═C(CF3)2, SF5 and N(SO2CF3)2,
pyridyl, pyrimidyl and triazinyl are substituted by at least one radical selected from NO2, F, Cl, Br, CN, CF3, SF5, OCF3, SCF3, SO2CF3, N═C(CF3)2, and N(SO2CF3)2;
or
R1 and Y together with the carbon atom of the C—O-group to which they are bonded form a 5 to 7 membered ring which may bear a C═O or C(CH3)2 group as ring member and wherein the 5 to 7 membered ring is fused with a benzene group, wherein the fused benzene group is unsubstituted or substituted with 1, 2, 3 or 4 substituents R4;
R2 represents CFRaRb, t-butyl, adamantyl, C2F5, n-C3F7, C3-C7-cycloalkyl, phenyl, naphthyl, pyridyl, pyrimidyl, triazinyl, wherein cycloalkyl is unsubstituted or substituted with 1 to 13 radicals selected from fluorine and CF3,
phenyl is substituted by at least one radical selected from NO2, F, Cl, Br, CN, CF3, SF5, OCF3, SCF3, SO2CF3, N═C(CF3)2, and N(SO2CF3)2,
naphthyl is unsubstituted or substituted with 1 to 7 radicals selected from CN, NO2, F, Cl, Br, C1-C4-haloalkyl, OCF3, SCF3, SO2CF3, N═C(CF3)2, SF5 and N(SO2CF3)2,
pyridyl, pyrimidyl and triazinyl are substituted by at least one radical selected from NO2, F, Cl, Br, CN, CF3, SF5, OCF3, SCF3, SO2CF3, N═C(CF3)2, and N(SO2CF3)2;
or
R2 and Y together with the carbon atom of the C—O-group to which they are bonded form a 5 to 7 membered ring which may bear a C═O or C(CH3)2 group as ring member and wherein the 5 to 7 membered ring is fused with a benzene group, wherein the fused benzene group is unsubstituted or substituted with 1, 2, 3 or 4 substituents R4;
Ra and Rb independently from each other represent halogen, CF3, CN and C6-C14-aryl, which is unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents selected from halogen, C1-C4-haloalkyl, C1-C4-haloalkoxy, SCF3, SO2CF3, NO2, N═C(CF3)2, SF5, N(SO2CF3)2 and CN;
R3 represents hydrogen, F, Cl, CN, CF3, OCF3, SCF3, methyl, ethyl, t-butyl, adamantyl, phenyl or hetaryl having 4 to 5 carbon atoms, wherein hetaryl has 1, 2 or 3 nitrogen atoms as ring members, wherein phenyl and hetaryl are unsubstituted or substituted by 1 or 2 identical or different radicals R5;
R4 represents CN, NO2, SF5, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-haloalkylsulfanyl, C1-C4-haloalkylsulfonyl, N═C(CF3)2 and N(SO2CF3)2;
R5 represents CN, F, C1, CF3, OCF3, SCF3, SO2CF3, NO2, N═C(CF3)2, SF5, and N(SO2CF3)2
with the proviso that the compounds of formula (I.a),
wherein
(R1, R2, R3), (R1′, R2′, R3′), (R1″, R2″, R3″) and (R1′″, R2′″, R3′″) are each selected from the definition given in one line of the following table
R1, R1′,
R2, R2′,
R3, R3′,
R1″, R1′″
R2″, R2′″
R3″, R3′″
1.
trifluoromethyl
trifluoromethyl
H
2.
trifluoromethyl
trifluoromethyl
CN
3.
trifluoromethyl
trifluoromethyl
F
4.
trifluoromethyl
trifluoromethyl
Cl
5.
trifluoromethyl
trifluoromethyl
pentafluorophenyl
6.
trifluoromethyl
trifluoromethyl
tetrafluoro-2-
(trifluoromethyl)phenyl
7.
trifluoromethyl
trifluoromethyl
tetrafluoro-3-
(trifluoromethyl)phenyl
8.
trifluoromethyl
trifluoromethyl
tetrafluoro-4-
(trifluoromethyl)phenyl
9.
trifluoromethyl
trifluoromethyl
tetrafluoro-2-
pyridyl
10.
trifluoromethyl
trifluoromethyl
tetrafluoro-3-
pyridyl
11.
trifluoromethyl
trifluoromethyl
tetrafluoro-4-
pyridyl
12.
trifluoromethyl
trifluoromethyl
tetrafluoro-2-
benzonitrile
13.
trifluoromethyl
trifluoromethyl
tetrafluoro-3-
benzonitrile
14.
trifluoromethyl
trifluoromethyl
tetrafluoro-4-
benzonitrile
15.
pentafluoroethyl
pentafluoroethyl
H
16.
pentafluoroethyl
pentafluoroethyl
CN
17.
pentafluoroethyl
pentafluoroethyl
F
18.
pentafluoroethyl
pentafluoroethyl
Cl
19.
pentafluoroethyl
pentafluoroethyl
pentafluorophenyl
20.
pentafluoroethyl
pentafluoroethyl
tetrafluoro-2-
(trifluoromethyl)phenyl
21.
pentafluoroethyl
pentafluoroethyl
tetrafluoro-3-
(trifluoromethyl)phenyl
22.
pentafluoroethyl
pentafluoroethyl
tetrafluoro-4-
(trifluoromethyl)phenyl
23.
pentafluoroethyl
pentafluoroethyl
tetrafluoro-2-
pyridyl
24.
pentafluoroethyl
pentafluoroethyl
tetrafluoro-3-
pyridyl
25.
pentafluoroethyl
pentafluoroethyl
tetrafluoro-4-
pyridyl
26.
pentafluoroethyl
pentafluoroethyl
tetrafluoro-2-
benzonitrile
27.
pentafluoroethyl
pentafluoroethyl
tetrafluoro-3-
benzonitrile
28.
pentafluoroethyl
pentafluoroethyl
tetrafluoro-4-
benzonitrile
29.
heptafluoro-n-
heptafluoro-n-
H
propyl
propyl
30.
heptafluoro-n-
heptafluoro-n-
CN
propyl
propyl
31.
heptafluoro-n-
heptafluoro-n-
F
propyl
propyl
32.
heptafluoro-n-
heptafluoro-n-
Cl
propyl
propyl
33.
heptafluoro-n-
heptafluoro-n-
pentafluorophenyl
propyl
propyl
34.
heptafluoro-n-
heptafluoro-n-
tetrafluoro-2-
propyl
propyl
(trifluoromethyl)phenyl
35.
heptafluoro-n-
heptafluoro-n-
tetrafluoro-3-
propyl
propyl
(trifluoromethyl)phenyl
36.
heptafluoro-n-
heptafluoro-n-
tetrafluoro-4-
propyl
propyl
(trifluoromethyl)phenyl
37.
heptafluoro-n-
heptafluoro-n-
tetrafluoro-2-
propyl
propyl
pyridyl
38.
heptafluoro-n-
heptafluoro-n-
tetrafluoro-3-
propyl
propyl
pyridyl
39.
heptafluoro-n-
heptafluoro-n-
tetrafluoro-4-
propyl
propyl
pyridyl
40.
heptafluoro-n-
heptafluoro-n-
tetrafluoro-2-
propyl
propyl
benzonitrile
41.
heptafluoro-n-
heptafluoro-n-
tetrafluoro-3-
propyl
propyl
benzonitrile
42.
heptafluoro-n-
heptafluoro-n-
tetrafluoro-4-
propyl
propyl
benzonitrile
43.
heptafluoro-
heptafluoro-
H
isopropyl
isopropyl
44.
heptafluoro-
heptafluoro-
CN
isopropyl
isopropyl
45.
heptafluoro-
heptafluoro-
F
isopropyl
isopropyl
46.
heptafluoro-
heptafluoro-
Cl
isopropyl
isopropyl
47.
heptafluor-iso-
heptafluoro-
pentafluorophenyl
propyl
isopropyl
48.
heptafluor-iso-
heptafluoro-
tetrafluoro-2-
propyl
isopropyl
(trifluoromethyl)phenyl
49.
heptafluoro-
heptafluoro-
tetrafluoro-3-
isopropyl
isopropyl
(trifluoromethyl)phenyl
50.
heptafluoro-
heptafluoro-
tetrafluoro-4-
isopropyl
isopropyl
(trifluoromethyl)phenyl
51.
heptafluoro-
heptafluoro-
tetrafluoro-2-
isopropyl
isopropyl
pyridyl
52.
heptafluoro-
heptafluoro-
tetrafluoro-3-
isopropyl
isopropyl
pyridyl
53.
heptafluoro-
heptafluoro-
tetrafluoro-4-
isopropyl
isopropyl
pyridyl
54.
heptafluoro-
heptafluoro-
tetrafluoro-2-
isopropyl
isopropyl
benzonitrile
55.
heptafluoro-
heptafluoro-
tetrafluoro-3-
isopropyl
isopropyl
benzonitrile
56.
heptafluoro-
heptafluoro-
tetrafluoro-4-
isopropyl
isopropyl
benzonitrile
57.
tert-butyl
tert-butyl
H
58.
tert-butyl
tert-butyl
CN
59.
tert-butyl
tert-butyl
F
60.
tert-butyl
tert-butyl
Cl
61.
tert-butyl
tert-butyl
pentafluorophenyl
62.
tert-butyl
tert-butyl
tetrafluoro-2-
(trifluoromethyl)phenyl
63.
tert-butyl
tert-butyl
tetrafluoro-3-
(trifluoromethyl)phenyl
64.
tert-butyl
tert-butyl
tetrafluoro-4-
(trifluoromethyl)phenyl
65.
tert-butyl
tert-butyl
tetrafluoro-2-
pyridyl
66.
tert-butyl
tert-butyl
tetrafluoro-3-
pyridyl
67.
tert-butyl
tert-butyl
tetrafluoro-4-
pyridyl
68.
tert-butyl
tert-butyl
tetrafluoro-2-
benzonitrile
69.
tert-butyl
tert-butyl
tetrafluoro-3-
benzonitrile
70.
tert-butyl
tert-butyl
tetrafluoro-4-
benzonitrile
71.
pentafluorophenyl
pentafluorophenyl
H
72.
pentafluorophenyl
pentafluorophenyl
CN
73.
pentafluorophenyl
pentafluorophenyl
F
74.
pentafluorophenyl
pentafluorophenyl
Cl
75.
pentafluorophenyl
pentafluorophenyl
pentafluorophenyl
76.
pentafluorophenyl
pentafluorophenyl
tetrafluoro-2-
(trifluoromethyl)phenyl
77.
pentafluorophenyl
pentafluorophenyl
tetrafluoro-3-
(trifluoromethyl)phenyl
78.
pentafluorophenyl
pentafluorophenyl
tetrafluoro-4-
(trifluoromethyl)phenyl
79.
pentafluorophenyl
pentafluorophenyl
tetrafluoro-2-
pyridyl
80.
pentafluorophenyl
pentafluorophenyl
tetrafluoro-3-
pyridyl
81.
pentafluorophenyl
pentafluorophenyl
tetrafluoro-4-
pyridyl
82.
pentafluorophenyl
pentafluorophenyl
tetrafluoro-2-
benzonitrile
83.
pentafluorophenyl
pentafluorophenyl
tetrafluoro-3-
benzonitrile
84.
pentafluorophenyl
pentafluorophenyl
tetrafluoro-4-
benzonitrile
85.
3,5-
3,5-
H
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
86.
3,5-
trifluoromethyl
H
bis(trifluoromethyl)-
phenyl
87.
3,5-
pentafluoroethyl
H
bis(trifluoromethyl)-
phenyl
88.
4-fluoro-3-
pentafluoroethyl
H
trifluoromethyl-
phenyl
89.
4-fluoro-3-
3,5-
H
trifluoromethyl-
bis(trifluoromethyl)-
phenyl
phenyl
90.
3,4,5-
3,4,5-
H
trifluorophenyl
trifluorophenyl
91.
3,4,5-
pentafluoroethyl
H
trifluorophenyl
92.
4-
4-
H
(trifluoromethyl)phenyl
(trifluoromethyl)phenyl
93.
4-
pentafluoroethyl
H
(trifluoromethyl)phenyl
94.
2,4,6-
2,4,6-
H
tris(trifluoromethyl)phenyl
tris(trifluoromethyl)phenyl
95.
2,4,6-
Pentafluoroethyl
H
tris(trifluoromethyl)phenyl
96.
3,5-
3,5-
CN
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
97.
2,4,6-
2,4,6-
CN
tris(trifluoromethyl)phenyl
tris(trifluoromethyl)phenyl
98.
3,5-
pentafluoroethyl
3,5-
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
99.
3,4-
3,4-
H
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
100.
3,4-
trifluoromethyl
H
bis(trifluoromethyl)-
phenyl
101.
3,4-
pentafluoroethyl
3,5-
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
102.
3,4-
pentafluoroethyl
H
bis(trifluoromethyl)-
phenyl
103.
3,4-
3,4-
CN
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
104.
4-cyano-3-
3,5-
H
(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
105.
4-cyano-3-
pentafluoroethyl
H
(trifluoromethyl)-
phenyl
106.
3,5-
pentafluoroethyl
CN
bis(trifluoromethyl)-
phenyl
107.
4-cyano-2,6-
4-cyano-2,6-
H
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
108.
4-cyano-2,6-
pentafluoroethyl
H
bis(trifluoromethyl)-
phenyl
109.
2,4-
2,6-
H
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
110.
2,4-
2,6-
CN
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
111.
4-(3′,5′-
pentafluoroethyl
H
bis(trifluoromethyl)phenyl)-
2,6-
bis(trifluoromethyl)-
phenyl
112.
3,5-
3,5-
CF3
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
113.
3,5-
trifluoromethyl
CF3
bis(trifluoromethyl)-
phenyl
114.
3,5-
pentafluoroethyl
CF3
bis(trifluoromethyl)-
phenyl
115.
3,4,5-
3,4,5-
CF3
trifluorophenyl
trifluorophenyl
116.
4-
4-
CF3
(trifluoromethyl)phenyl
(trifluoromethyl)phenyl
117.
tert-butyl
heptafluoro-n-
H
propyl
118.
tert-butyl
tert-butyl
tert-butyl
are excluded.

700 more elements

Dependencies are inferred from the claim text.

Facts

Application: 18/549,034Filed 8 Mar 2022
Priority: EP 21161845.910 Mar 2021
Published: 25 Jul 2024
Term ends: Not estimatedThe source records don’t support an estimate.

Classification20 codes

C07C 49/92
Ketones; Ketenes; Dimeric ketenes ; Ketonic chelates: ketonic chelates
C07C 45/77
Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds: preparation of…
C07C 255/40
Having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring: the carbon skeleton…
C07F 5/003
Compounds containing elements of Groups 3 or 13 of the Periodic Table: without C-Metal linkages

Family

No related US applications are recorded in the indexed filing history.

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Abstract

Compound of the general formula (I)

wherein
L1;
L2;
L3;
and L4 are independently from each other selected from a bidentate ligand having the general formula (II)
wherein
Y represents N or CR3;
R1 represents CFRaRb, t-butyl, adamantyl, C2F5, n-C3F7, C3-C7-cycloalkyl, phenyl, naphthyl, pyridyl, pyrimidyl, triazinyl, wherein cycloalkyl is unsubstituted or substituted with 1 to 13 radicals selected from fluorine and CF3,
phenyl is substituted by at least one radical selected from NO2, F, Cl, Br, CN, CF3, SF5, OCF3, SCF3, SO2CF3, N═C(CF3)2, and N(SO2CF3)2,
naphthyl is unsubstituted or substituted with 1 to 7 radicals selected from CN, NO2, F, Cl, Br, C1-C4-haloalkyl, OCF3, SCF3, SO2CF3, N═C(CF3)2, SF5 and N(SO2CF3)2,
pyridyl, pyrimidyl and triazinyl are substituted by at least one radical selected from NO2, F, Cl, Br, CN, CF3, SF5, OCF3, SCF3, SO2CF3, N═C(CF3)2, and N(SO2CF3)2;
or
R1 and Y together with the carbon atom of the C—O-group to which they are bonded form a 5 to 7 membered ring which may bear a C═O or C(CH3)2 group as ring member and wherein the 5 to 7 membered ring is fused with a benzene group, wherein the fused benzene group is unsubstituted or substituted with 1, 2, 3 or 4 substituents R4;
R2 represents CFRaRb, t-butyl, adamantyl, C2F5, n-C3F7, C3-C7-cycloalkyl, phenyl, naphthyl, pyridyl, pyrimidyl, triazinyl, wherein cycloalkyl is unsubstituted or substituted with 1 to 13 radicals selected from fluorine and CF3,
phenyl is substituted by at least one radical selected from NO2, F, Cl, Br, CN, CF3, SF5, OCF3, SCF3, SO2CF3, N═C(CF3)2, and N(SO2CF3)2,
naphthyl is unsubstituted or substituted with 1 to 7 radicals selected from CN, NO2, F, Cl, Br, C1-C4-haloalkyl, OCF3, SCF3, SO2CF3, N═C(CF3)2, SF5 and N(SO2CF3)2,
pyridyl, pyrimidyl and triazinyl are substituted by at least one radical selected from NO2, F, Cl, Br, CN, CF3, SF5, OCF3, SCF3, SO2CF3, N═C(CF3)2, and N(SO2CF3)2;
or
R2 and Y together with the carbon atom of the C—O-group to which they are bonded form a 5 to 7 membered ring which may bear a C═O or C(CH3)2 group as ring member and wherein the 5 to 7 membered ring is fused with a benzene group, wherein the fused benzene group is unsubstituted or substituted with 1, 2, 3 or 4 substituents R4;
Ra and Rb independently from each other represent halogen, CF3, CN and C6-C14-aryl, which is unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents selected from halogen, C1-C4-haloalkyl, C1-C4-haloalkoxy, SCF3, SO2CF3, NO2, N═C(CF3)2, SF5, N(SO2CF3)2 and CN;
R3 represents hydrogen, F, Cl, CN, CF3, OCF3, SCF3, methyl, ethyl, t-butyl, adamantyl, phenyl or hetaryl having 4 to 5 carbon atoms, wherein hetaryl has 1, 2 or 3 nitrogen atoms as ring members, wherein phenyl and hetaryl are unsubstituted or substituted by 1 or 2 identical or different radicals R5;
R4 represents CN, NO2, SF5, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-haloalkylsulfanyl, C1-C4-haloalkylsulfonyl, N═C(CF3)2 and N(SO2CF3)2;
R5 represents CN, F, C1, CF3, OCF3, SCF3, SO2CF3, NO2, N═C(CF3)2, SF5, and N(SO2CF3)2
with the proviso that the compounds of formula (I.a),
wherein
(R1, R2, R3), (R1′, R2′, R3′), (R1″, R2″, R3″) and (R1′″, R2′″, R3′″) are each selected from the definition given in one line of the following table
R1, R1′,
R2, R2′,
R3, R3′,
R1″, R1′″
R2″, R2′″
R3″, R3′″
1.
trifluoromethyl
trifluoromethyl
H
2.
trifluoromethyl
trifluoromethyl
CN
3.
trifluoromethyl
trifluoromethyl
F
4.
trifluoromethyl
trifluoromethyl
Cl
5.
trifluoromethyl
trifluoromethyl
pentafluorophenyl
6.
trifluoromethyl
trifluoromethyl
tetrafluoro-2-
(trifluoromethyl)phenyl
7.
trifluoromethyl
trifluoromethyl
tetrafluoro-3-
(trifluoromethyl)phenyl
8.
trifluoromethyl
trifluoromethyl
tetrafluoro-4-
(trifluoromethyl)phenyl
9.
trifluoromethyl
trifluoromethyl
tetrafluoro-2-
pyridyl
10.
trifluoromethyl
trifluoromethyl
tetrafluoro-3-
pyridyl
11.
trifluoromethyl
trifluoromethyl
tetrafluoro-4-
pyridyl
12.
trifluoromethyl
trifluoromethyl
tetrafluoro-2-
benzonitrile
13.
trifluoromethyl
trifluoromethyl
tetrafluoro-3-
benzonitrile
14.
trifluoromethyl
trifluoromethyl
tetrafluoro-4-
benzonitrile
15.
pentafluoroethyl
pentafluoroethyl
H
16.
pentafluoroethyl
pentafluoroethyl
CN
17.
pentafluoroethyl
pentafluoroethyl
F
18.
pentafluoroethyl
pentafluoroethyl
Cl
19.
pentafluoroethyl
pentafluoroethyl
pentafluorophenyl
20.
pentafluoroethyl
pentafluoroethyl
tetrafluoro-2-
(trifluoromethyl)phenyl
21.
pentafluoroethyl
pentafluoroethyl
tetrafluoro-3-
(trifluoromethyl)phenyl
22.
pentafluoroethyl
pentafluoroethyl
tetrafluoro-4-
(trifluoromethyl)phenyl
23.
pentafluoroethyl
pentafluoroethyl
tetrafluoro-2-
pyridyl
24.
pentafluoroethyl
pentafluoroethyl
tetrafluoro-3-
pyridyl
25.
pentafluoroethyl
pentafluoroethyl
tetrafluoro-4-
pyridyl
26.
pentafluoroethyl
pentafluoroethyl
tetrafluoro-2-
benzonitrile
27.
pentafluoroethyl
pentafluoroethyl
tetrafluoro-3-
benzonitrile
28.
pentafluoroethyl
pentafluoroethyl
tetrafluoro-4-
benzonitrile
29.
heptafluoro-n-
heptafluoro-n-
H
propyl
propyl
30.
heptafluoro-n-
heptafluoro-n-
CN
propyl
propyl
31.
heptafluoro-n-
heptafluoro-n-
F
propyl
propyl
32.
heptafluoro-n-
heptafluoro-n-
Cl
propyl
propyl
33.
heptafluoro-n-
heptafluoro-n-
pentafluorophenyl
propyl
propyl
34.
heptafluoro-n-
heptafluoro-n-
tetrafluoro-2-
propyl
propyl
(trifluoromethyl)phenyl
35.
heptafluoro-n-
heptafluoro-n-
tetrafluoro-3-
propyl
propyl
(trifluoromethyl)phenyl
36.
heptafluoro-n-
heptafluoro-n-
tetrafluoro-4-
propyl
propyl
(trifluoromethyl)phenyl
37.
heptafluoro-n-
heptafluoro-n-
tetrafluoro-2-
propyl
propyl
pyridyl
38.
heptafluoro-n-
heptafluoro-n-
tetrafluoro-3-
propyl
propyl
pyridyl
39.
heptafluoro-n-
heptafluoro-n-
tetrafluoro-4-
propyl
propyl
pyridyl
40.
heptafluoro-n-
heptafluoro-n-
tetrafluoro-2-
propyl
propyl
benzonitrile
41.
heptafluoro-n-
heptafluoro-n-
tetrafluoro-3-
propyl
propyl
benzonitrile
42.
heptafluoro-n-
heptafluoro-n-
tetrafluoro-4-
propyl
propyl
benzonitrile
43.
heptafluoro-
heptafluoro-
H
isopropyl
isopropyl
44.
heptafluoro-
heptafluoro-
CN
isopropyl
isopropyl
45.
heptafluoro-
heptafluoro-
F
isopropyl
isopropyl
46.
heptafluoro-
heptafluoro-
Cl
isopropyl
isopropyl
47.
heptafluor-iso-
heptafluoro-
pentafluorophenyl
propyl
isopropyl
48.
heptafluor-iso-
heptafluoro-
tetrafluoro-2-
propyl
isopropyl
(trifluoromethyl)phenyl
49.
heptafluoro-
heptafluoro-
tetrafluoro-3-
isopropyl
isopropyl
(trifluoromethyl)phenyl
50.
heptafluoro-
heptafluoro-
tetrafluoro-4-
isopropyl
isopropyl
(trifluoromethyl)phenyl
51.
heptafluoro-
heptafluoro-
tetrafluoro-2-
isopropyl
isopropyl
pyridyl
52.
heptafluoro-
heptafluoro-
tetrafluoro-3-
isopropyl
isopropyl
pyridyl
53.
heptafluoro-
heptafluoro-
tetrafluoro-4-
isopropyl
isopropyl
pyridyl
54.
heptafluoro-
heptafluoro-
tetrafluoro-2-
isopropyl
isopropyl
benzonitrile
55.
heptafluoro-
heptafluoro-
tetrafluoro-3-
isopropyl
isopropyl
benzonitrile
56.
heptafluoro-
heptafluoro-
tetrafluoro-4-
isopropyl
isopropyl
benzonitrile
57.
tert-butyl
tert-butyl
H
58.
tert-butyl
tert-butyl
CN
59.
tert-butyl
tert-butyl
F
60.
tert-butyl
tert-butyl
Cl
61.
tert-butyl
tert-butyl
pentafluorophenyl
62.
tert-butyl
tert-butyl
tetrafluoro-2-
(trifluoromethyl)phenyl
63.
tert-butyl
tert-butyl
tetrafluoro-3-
(trifluoromethyl)phenyl
64.
tert-butyl
tert-butyl
tetrafluoro-4-
(trifluoromethyl)phenyl
65.
tert-butyl
tert-butyl
tetrafluoro-2-
pyridyl
66.
tert-butyl
tert-butyl
tetrafluoro-3-
pyridyl
67.
tert-butyl
tert-butyl
tetrafluoro-4-
pyridyl
68.
tert-butyl
tert-butyl
tetrafluoro-2-
benzonitrile
69.
tert-butyl
tert-butyl
tetrafluoro-3-
benzonitrile
70.
tert-butyl
tert-butyl
tetrafluoro-4-
benzonitrile
71.
pentafluorophenyl
pentafluorophenyl
H
72.
pentafluorophenyl
pentafluorophenyl
CN
73.
pentafluorophenyl
pentafluorophenyl
F
74.
pentafluorophenyl
pentafluorophenyl
Cl
75.
pentafluorophenyl
pentafluorophenyl
pentafluorophenyl
76.
pentafluorophenyl
pentafluorophenyl
tetrafluoro-2-
(trifluoromethyl)phenyl
77.
pentafluorophenyl
pentafluorophenyl
tetrafluoro-3-
(trifluoromethyl)phenyl
78.
pentafluorophenyl
pentafluorophenyl
tetrafluoro-4-
(trifluoromethyl)phenyl
79.
pentafluorophenyl
pentafluorophenyl
tetrafluoro-2-
pyridyl
80.
pentafluorophenyl
pentafluorophenyl
tetrafluoro-3-
pyridyl
81.
pentafluorophenyl
pentafluorophenyl
tetrafluoro-4-
pyridyl
82.
pentafluorophenyl
pentafluorophenyl
tetrafluoro-2-
benzonitrile
83.
pentafluorophenyl
pentafluorophenyl
tetrafluoro-3-
benzonitrile
84.
pentafluorophenyl
pentafluorophenyl
tetrafluoro-4-
benzonitrile
85.
3,5-
3,5-
H
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
86.
3,5-
trifluoromethyl
H
bis(trifluoromethyl)-
phenyl
87.
3,5-
pentafluoroethyl
H
bis(trifluoromethyl)-
phenyl
88.
4-fluoro-3-
pentafluoroethyl
H
trifluoromethyl-
phenyl
89.
4-fluoro-3-
3,5-
H
trifluoromethyl-
bis(trifluoromethyl)-
phenyl
phenyl
90.
3,4,5-
3,4,5-
H
trifluorophenyl
trifluorophenyl
91.
3,4,5-
pentafluoroethyl
H
trifluorophenyl
92.
4-
4-
H
(trifluoromethyl)phenyl
(trifluoromethyl)phenyl
93.
4-
pentafluoroethyl
H
(trifluoromethyl)phenyl
94.
2,4,6-
2,4,6-
H
tris(trifluoromethyl)phenyl
tris(trifluoromethyl)phenyl
95.
2,4,6-
Pentafluoroethyl
H
tris(trifluoromethyl)phenyl
96.
3,5-
3,5-
CN
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
97.
2,4,6-
2,4,6-
CN
tris(trifluoromethyl)phenyl
tris(trifluoromethyl)phenyl
98.
3,5-
pentafluoroethyl
3,5-
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
99.
3,4-
3,4-
H
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
100.
3,4-
trifluoromethyl
H
bis(trifluoromethyl)-
phenyl
101.
3,4-
pentafluoroethyl
3,5-
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
102.
3,4-
pentafluoroethyl
H
bis(trifluoromethyl)-
phenyl
103.
3,4-
3,4-
CN
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
104.
4-cyano-3-
3,5-
H
(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
105.
4-cyano-3-
pentafluoroethyl
H
(trifluoromethyl)-
phenyl
106.
3,5-
pentafluoroethyl
CN
bis(trifluoromethyl)-
phenyl
107.
4-cyano-2,6-
4-cyano-2,6-
H
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
108.
4-cyano-2,6-
pentafluoroethyl
H
bis(trifluoromethyl)-
phenyl
109.
2,4-
2,6-
H
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
110.
2,4-
2,6-
CN
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
111.
4-(3′,5′-
pentafluoroethyl
H
bis(trifluoromethyl)phenyl)-
2,6-
bis(trifluoromethyl)-
phenyl
112.
3,5-
3,5-
CF3
bis(trifluoromethyl)-
bis(trifluoromethyl)-
phenyl
phenyl
113.
3,5-
trifluoromethyl
CF3
bis(trifluoromethyl)-
phenyl
114.
3,5-
pentafluoroethyl
CF3
bis(trifluoromethyl)-
phenyl
115.
3,4,5-
3,4,5-
CF3
trifluorophenyl
trifluorophenyl
116.
4-
4-
CF3
(trifluoromethyl)phenyl
(trifluoromethyl)phenyl
117.
tert-butyl
heptafluoro-n-
H
propyl
118.
tert-butyl
tert-butyl
tert-butyl
are excluded.

700 more elements

Facts

Application

18/549,034Filed 8 Mar 2022

Priority

EP 21161845.910 Mar 2021

Published

25 Jul 2024

Term ends

Not estimatedThe source records don’t support an estimate.

Classification20 codes

C07C 49/92
Ketones; Ketenes; Dimeric ketenes ; Ketonic chelates: ketonic chelates
C07C 45/77
Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds: preparation of…
C07C 255/40
Having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring: the carbon skeleton…
C07F 5/003
Compounds containing elements of Groups 3 or 13 of the Periodic Table: without C-Metal linkages