1. A compound of Formula I
or a pharmaceutically acceptable salt thereof, wherein:
R1 is selected from \u2014(CH2)0-2-heteroaryl, \u2014(CH2)0-2-aryl, C3-8 cycloalkyl, and a 4 to 8 membered heterocycloalkyl group, wherein said groups are each independently optionally substituted;
R2 is halogen;
R3 is selected from hydrogen, C1-4 alkyl, C1-4 haloalkyl, CN, \u2014O\u2014C1-4 alkyl, C3-4 cycloalkyl, C3-4 cyclo haloalkyl, \u2014O\u2014C1-4 haloalkyl, and halogen;
R4 is selected from 5 to 7 membered heterocyclyl-R14, and A6-L-R9;
R5 is selected from hydrogen, C1-4 alkyl, C1-4 haloalkyl, hydroxyl, CN, \u2014O\u2014C1-4 alkyl, \u2014O\u2014C1-4 haloalkyl, C3-4 cycloalkyl, C3-4 cyclo haloalkyl, and halogen;
R6 is selected from hydrogen, C1-4 alkyl, C1-4 haloalkyl, CN, \u2014O\u2014C1-4 alkyl, C3-4 cycloalkyl, C3-4 cyclo haloalkyl, \u2014O\u2014C1-4 haloalkyl, and halogen;
R7 is selected from hydrogen, C1-4 alkyl, C1-4 haloalkyl, O\u2014C1-3 alkyl, and halogen;
A6 is NR8;
L is selected from C0-3-alkylene, \u2014CHD-, \u2014CD2-, C3-8 branched alkylene, and C3-8 branched haloalkylene;
R8 is selected from hydrogen and C1-4 alkyl;
R9 is selected from C3-8 cycloalkyl, \u2014(CH2)0-2 heteroaryl, (CH2)0-2-4 to 8 member heterocycloalkyl, and (CH2)0-2-aryl, wherein said groups are optionally substituted; and
R14 is selected from hydrogen, phenyl, halogen, hydroxy, C1-4-alkyl, C3-6-branched alkyl, C1-4-haloalkyl, CF3, \u2550O, and O\u2014C1-4-alkyl.
2. A compound of claim 1, wherein:
R1 is selected from \u2014(CH2)0-2-heteroaryl, and \u2014(CH2)0-2-aryl, wherein said groups are each independently optionally substituted with one to three substituents selected from \u2014NH2, \u2014F, \u2014Cl, \u2014OH, \u2014C1-4 alkyl, \u2014C1-4 haloalkyl, \u2014C3-6 branched alkyl, C3-6 branched haloalkyl, \u2014C3-7 cyclo alkyl, \u2014C3-7 cyclo haloalkyl, \u2014(CH2)1-3\u2014O\u2014C1-2 alkyl, \u2014(CH2)1-3\u2014O\u2014C1-2 haloalkyl, \u2014(CH2)0-2\u2014O\u2014(CH2)2-3\u2014O\u2014C1-2 alkyl, \u2014(CH2)0-2\u2014O\u2014(CH2)2-3\u2014O\u2014C1-2 haloalkyl, \u2014O\u2014C1-4 alkyl, \u2014O\u2014C1-4 haloalkyl, \u2014O\u2014C3-6 branched alkyl, \u2014O\u2014C3-6 branched haloalkyl, \u2014O\u2014C3-7 cyclo alkyl, \u2014O\u2014C3-7 cyclo haloalkyl, \u2014O\u2014(CH2)1-2\u2014C3-6 cycloalkyl-R14, \u2014O\u2014(CH2)1-2\u2014C4-6 heterocycloalkyl-R14, \u2014NH\u2014C1-4 alkyl, \u2014NH\u2014C2-4 haloalkyl, \u2014NH\u2014C3-8 branched alkyl, \u2014NH\u2014C3-8 branched haloalkyl, \u2014NH\u2014C3-7 cyclo alkyl, \u2014NH\u2014C3-7 cyclo haloalkyl, \u2014NH\u2014C(O)\u2014C1-4 alkyl, \u2014NH\u2014C(O)\u2014C1-4 haloalkyl, \u2014NH\u2014C(O)\u2014C3-8 branched alkyl, \u2014NH\u2014C(O)\u2014C3-8 branched haloalkyl, \u2014NH\u2014C(O)\u2014C3-7 cyclo alkyl, \u2014NH\u2014C(O)\u2014C3-7 cyclo haloalkyl, \u2014NH\u2014C(O)\u2014CH2\u2014O\u2014C1-4 alkyl, \u2014NH\u2014C(O)\u2014CH2\u2014O\u2014C1-4 haloalkyl, \u2014NH\u2014C(O)\u2014O\u2014C1-4 alkyl, \u2014NH\u2014C(O)O\u2014C2-4 haloalkyl, \u2014NH\u2014C(O)\u2014O\u2014C3-8 branched alkyl, \u2014NH\u2014C(O)O\u2014C3-8 branched haloalkyl, \u2014NH\u2014C(O)\u2014O\u2014C3-7 cyclo alkyl, \u2014NH\u2014C(O)\u2014O\u2014C3-7 cyclo haloalkyl, \u2014NH\u2014SO2\u2014C1-4 alkyl, \u2014NH\u2014SO2\u2014C1-4 haloalkyl, \u2014NH\u2014SO2\u2014C3-8 branched alkyl, \u2014NH\u2014SO2\u2014C3-8 branched haloalkyl, \u2014NH\u2014SO2\u2014C3-5 cycloalkyl, \u2014NH\u2014SO2\u2014C3-5 cyclo haloalkyl, \u2014C(O)\u2014O\u2014C1-4 alkyl, \u2014C(O)\u2014O\u2014C2-4 halo-alky, \u2014C(O)\u2014O\u2014C3-6 branched alkyl, \u2014C(O)O\u2014C3-6 branched haloalkyl, \u2014C(O)\u2014O\u2014C3-7 cyclo alkyl, \u2014NH\u2014C(O)\u2014O\u2014C3-7 cyclo haloalkyl, \u2014C(O)\u2014C1-4 alkyl, \u2014C(O)C2-4 haloalkyl, \u2014C(O)\u2014C3-8 branched alkyl, \u2014C(O)\u2014C3-8 branched haloalkyl, \u2014C(O)\u2014C3-7 cyclo alkyl, \u2014NH\u2014C(O)\u2014O\u2014C3-7 cyclo haloalkyl, \u2014C(O)\u2014CH2\u2014O\u2014C1-4 alkyl, \u2014C(O)\u2014CH2\u2014O\u2014C1-4 haloalkyl, \u2014SO2\u2014C1-4 alkyl, \u2014SO2\u2014C1-4 haloalkyl, \u2014SO2\u2014C3-8 branched alkyl, \u2014SO2\u2014C3-8 branched haloalkyl, \u2014SO2\u2014C3-5 cycloalkyl, and \u2014SO2\u2014C3-5 cyclo haloalkyl, \u2014C(O)\u2014NR15R16, and \u2014SO2\u2014NR15R16, and further wherein, any two said substituents along with the atoms to which they are attached can form a ring;
R15 and R16 are independently selected from hydrogen, hydroxyl, alkyl, branched alkyl, haloalkyl, branched haloalkyl, alkoxy, cycloalkyl and heterocycloalkyl; alternatively, R15 and R16 along with the nitrogen atom to which they are attached can be taken together to form an optionally substituted four to six membered heteroaromatic, or non-aromatic heterocyclic ring.
3. A compound of claim 1, wherein:
R1 is selected from \u2014(CH2)0-2-heteroaryl, and \u2014(CH2)0-2-aryl, wherein said groups are each independently optionally substituted with one to three substituents selected from \u2014NH2, F, Cl, \u2014OH, \u2014C1-4 alkyl, \u2014NH\u2014C1-4 alkyl, \u2014C1-4 haloalkyl, \u2014C3-6 branched alkyl, \u2014(CH2)1-3\u2014O\u2014C1-2 alkyl, \u2014NH\u2014C(O)\u2014CH2\u2014O\u2014C1-4 alkyl, \u2014NH\u2014C(O)\u2014C1-4 alkyl, \u2014NH\u2014C(O)\u2014C3-8 branched alkyl, \u2014O\u2014C3-6 branched alkyl, \u2014NH\u2014C(O)O\u2014C1-4 alkyl, \u2014NH\u2014SO2\u2014C1-4 alkyl, \u2014NH\u2014SO2\u2014C3-8 branched alkyl, \u2014NH\u2014SO2\u2014C3-5 cycloalkyl, (CH2)0-2\u2014O\u2014(CH2)2-3\u2014O\u2014C1-2 alkyl, \u2014O\u2014C1-4 alkyl, \u2014C(O)O\u2014C3-6 branched alkyl, \u2014C(O)C1-4 alkyl, \u2014C(O)\u2014O\u2014C1-4 alkyl, \u2014C(O)\u2014C3-8 branched alkyl, \u2014C(O)\u2014CH2\u2014O\u2014C1-4 alkyl, \u2014SO2\u2014C1-4 alkyl, \u2014SO2\u2014C3-8 branched alkyl, \u2014O\u2014(CH2)1-2\u2014C3-6 cycloalkyl-R14, \u2014O\u2014(CH2)1-2\u2014C4-6 heterocycloalkyl-R14, \u2014SO2\u2014NR15R16, and \u2014SO2\u2014C3-5 cycloalkyl;
R3 is hydrogen;
R4 is selected from piperidinyl, morpholinyl, pyrrolidinyl, and A6-L-R9; wherein each said piperidinyl, morpholinyl, pyrrolidinyl group is substituted with R14;
R5 is selected from hydrogen, Cl, F, and CF3;
R6 is hydrogen;
R7 is selected from hydrogen, F, and Cl;
L is selected from C0-3-alkylene, \u2014CD2-, and C3-8 branched alkylene;
R9 is selected from C1-3 alkyl, C3-7 cycloalkyl, C4-6 branched alkyl, \u2014(CH2)1-3\u2014O\u2014C1-4 alkyl, \u2014(CH2)-pyridyl, (CH2)-4 to 8 member heterocycloalkyl, (CH2)-4 to 8 member heterocycloalkyl, and (CH2)-phenyl, wherein said groups are optionally substituted with one to three substituents selected from hydrogen, halogen, C1-4 alkyl, C1-4 haloalkyl, \u2014OH, CN, \u2550O, C(O)\u2014CH3, \u2014O\u2014C1-3 alkyl, \u2014O\u2014C1-3 haloalkyl, \u2014O\u2014(CH2)2-3\u2014O\u2014C1-2 alkyl, \u2014C(O)\u2014C1-4 alkyl, and \u2014NH\u2014C(O)\u2014C1-4 alkyl;
R14 is selected from phenyl, halogen, hydroxyl, C1-2-alkyl, CF3, and hydrogen; and
R15 and R16 are independently selected from hydrogen, hydroxyl, alkyl, branched alkyl, haloalkyl, branched haloalkyl, alkoxy, cycloalkyl and heterocycloalkyl; alternatively, R15 and R16 along with the nitrogen atom to which they are attached can be taken together to form an optionally substituted four to six membered heteroaromatic, or non-aromatic heterocyclic ring.
4. A compound of claim 1, wherein:
R1 is selected from C3-8 cycloalkyl, and a 4 to 8 membered heterocycloalkyl group, wherein said groups are each independently optionally substituted with one to three substituents selected from \u2014NH2, \u2014F, \u2014OH, \u2550O, \u2014C1-4 alkyl, \u2014C1-4 haloalkyl, \u2014C3-6 branched alkyl, C3-6 branched haloalkyl, \u2014C3-7 cyclo alkyl, \u2014C3-7 cyclo haloalkyl, \u2014(CH2)1-3\u2014O\u2014C1-2 alkyl, \u2014(CH2)1-3\u2014O\u2014C1-2 haloalkyl, \u2014(CH2)0-2\u2014O\u2014(CH2)2-3\u2014O\u2014C1-2 alkyl, \u2014(CH2)0-2\u2014O\u2014(CH2)2-3\u2014O\u2014C1-2 haloalkyl, \u2014O\u2014C1-4 alkyl, \u2014O\u2014C1-4 haloalkyl, \u2014O\u2014C3-6 branched alkyl, \u2014O\u2014C3-6 branched haloalkyl, \u2014O\u2014C3-7 cyclo alkyl, \u2014O\u2014C3-7 cyclo haloalkyl, \u2014O\u2014(CH2)1-2\u2014C3-6 cycloalkyl-R14, \u2014O\u2014(CH2)1-2\u2014C4-6 heterocycloalkyl-R14, \u2014NH\u2014C1-4 alkyl, \u2014NH\u2014C2-4 haloalkyl, \u2014NH\u2014C3-8 branched alkyl, \u2014NH\u2014C3-8 branched haloalkyl, \u2014NH\u2014C3-7 cyclo alkyl, \u2014NH\u2014C3-7 cyclo haloalkyl, \u2014NH\u2014C(O)\u2014C1-4 alkyl, \u2014NH\u2014C(O)\u2014C1-4 haloalkyl, \u2014NH\u2014C(O)\u2014C3-8 branched alkyl, \u2014NH\u2014C(O)\u2014C3-8 branched haloalkyl, \u2014NH\u2014C(O)\u2014C3-7 cyclo alkyl, \u2014NH\u2014C(O)\u2014C3-7 cyclo haloalkyl, \u2014NH\u2014C(O)\u2014CH2\u2014O\u2014C1-4 alkyl, \u2014NH\u2014C(O)\u2014CH2\u2014O\u2014C1-4 haloalkyl, \u2014NH\u2014C(O)\u2014O\u2014C1-4 alkyl, \u2014NH\u2014C(O)O\u2014C2-4 haloalkyl, \u2014NH\u2014C(O)\u2014O\u2014C3-8 branched alkyl, \u2014NH\u2014C(O)O\u2014C3-8 branched haloalkyl, \u2014NH\u2014C(O)\u2014O\u2014C3-7 cyclo alkyl, \u2014NH\u2014C(O)\u2014O\u2014C3-7 cyclo haloalkyl, \u2014NH\u2014SO2\u2014C1-4 alkyl, \u2014NH\u2014SO2\u2014C1-4 haloalkyl, \u2014NH\u2014SO2\u2014C3-8 branched alkyl, \u2014NH\u2014SO2\u2014C3-8 branched haloalkyl, \u2014NH\u2014SO2\u2014C3-5 cycloalkyl, \u2014NH\u2014SO2\u2014C3-5 halo-cycloalkyl, \u2014C(O)\u2014O\u2014C1-4 alkyl, \u2014C(O)\u2014O\u2014C2-4 halo-alky, \u2014C(O)\u2014O\u2014C3-6 branched alkyl, \u2014C(O)O\u2014C3-6 branched haloalkyl, \u2014C(O)\u2014O\u2014C3-7 cyclo alkyl, \u2014NH\u2014C(O)\u2014O\u2014C3-7 cyclo haloalkyl, \u2014C(O)\u2014C1-4 alkyl, \u2014C(O)C2-4 haloalkyl, \u2014C(O)\u2014C3-8 branched alkyl, \u2014C(O)\u2014C3-8 branched haloalkyl, \u2014C(O)\u2014C3-7 cyclo alkyl, \u2014NH\u2014C(O)\u2014O\u2014C3-7 cyclo haloalkyl, \u2014C(O)\u2014CH2\u2014O\u2014C1-4 alkyl, \u2014C(O)\u2014CH2\u2014O\u2014C1-4 haloalkyl, \u2014SO2\u2014C1-4 alkyl, \u2014SO2\u2014C1-4 haloalkyl, \u2014SO2\u2014C3-8 branched alkyl, \u2014SO2\u2014C3-8 branched haloalkyl, \u2014SO2\u2014C3-5 cycloalkyl, and \u2014SO2\u2014C3-5 cyclo haloalkyl;
\u2014C(O)\u2014NR15R16, and \u2014SO2\u2014NR15R16, and further wherein, any two said substituents along with the atoms to which they are attached can form a ring;
R15 and R16 are independently selected from hydrogen, hydroxyl, alkyl, branched alkyl, haloalkyl, branched haloalkyl, alkoxy, cycloalkyl and heterocycloalkyl; alternatively, R15 and R16 along with the nitrogen atom to which they are attached can be taken together to form an optionally substituted four to six membered heteroaromatic, or non-aromatic heterocyclic ring.
5. A compound of claim 1, wherein:
R1 is selected from C3-8 cycloalkyl, and a 4 to 8 membered heterocycloalkyl group, wherein said groups are each independently optionally substituted with one to three substituents selected from the group consisting of \u2014NH2, F, \u2014OH, \u2550O, \u2014C1-4 alkyl, \u2014NH\u2014C1-4 alkyl, \u2014C1-4 haloalkyl, \u2014C3-6 branched alkyl, \u2014(CH2)1-3\u2014O\u2014C1-2 alkyl, \u2014NH\u2014C(O)\u2014CH2\u2014O\u2014C1-4 alkyl, \u2014NH\u2014C(O)\u2014C1-4 alkyl, \u2014NH\u2014C(O)\u2014C3-8 branched alkyl, \u2014O\u2014C3-6 branched alkyl, \u2014NH\u2014C(O)O\u2014C1-4 alkyl, \u2014NH\u2014SO2\u2014C1-4 alkyl, \u2014NH\u2014SO2\u2014C3-8 branched alkyl, \u2014NH\u2014SO2\u2014C3-5 cycloalkyl, (CH2)0-2\u2014O\u2014(CH2)2-3\u2014O\u2014C1-2 alkyl, \u2014O\u2014C1-4 alkyl, \u2014C(O)O\u2014C3-6 branched alkyl, \u2014C(O)C1-4 alkyl, \u2014C(O)\u2014O\u2014C1-4 alkyl, \u2014C(O)\u2014C3-8 branched alkyl, \u2014C(O)\u2014CH2\u2014O\u2014C1-4 alkyl, \u2014SO2\u2014C1-4 alkyl, \u2014SO2\u2014C3-8 branched alkyl, and \u2014SO2\u2014C3-5 cycloalkyl;
R3 is hydrogen;
R4 is selected from piperidinyl, morpholinyl, pyrrolidinyl, and A6-L-R9; wherein each said piperidinyl, morpholinyl, pyrrolidinyl group is substituted with R14;
R5 is selected from hydrogen, F, Cl, and CF3;
R6 is selected from hydrogen, F, and Cl;
R7 is selected from hydrogen, F, and Cl;
L is selected from C0-3-alkylene, \u2014CD2-, and C3-8 branched alkylene;
R9 is selected from C3-7 cycloalkyl, (CH2)-pyridyl, (CH2)-4 to 8 member heterocycloalkyl, (CH2)-4 to 8 member heterocycloalkyl, and (CH2)-phenyl, wherein said groups are optionally substituted with one to three substituents selected from hydrogen, halogen, C1-4 alkyl, C1-4 haloalkyl, \u2014OH, CN, \u2550O, C(O)\u2014CH3, \u2014O\u2014C1-3 alkyl, \u2014O\u2014C1-3 haloalkyl, \u2014O\u2014(CH2)2-3\u2014O\u2014C1-2 alkyl, \u2014C(O)\u2014C1-4 alkyl, and \u2014NH\u2014C(O)\u2014C1-4 alkyl; and
R14 is selected from phenyl, halogen, hydroxy, C1-2-alkyl, and hydrogen.
6. A compound of claim 1, wherein:
R1 is selected from piperidinyl, morpholinyl, 1-methylpiperidinyl, tetrahydro-pyran, pyrrolidinyl, tetrahydro-furan, azetidine, pyrrolidin-2-one, azepane, and 1,4-oxazepane, wherein said R1 groups are each independently optionally substituted with one to three substituents selected from F, OH, NH2, CO-methyl, \u2014NH-methyl, ethyl, fluoro-ethyl, trifluoro-ethyl, (CH2)2-methoxy, SO2\u2014CH3, COO\u2014CH3, SO2-ethyl, SO2-cyclopropyl, methyl, SO2\u2014CH\u2014(CH3)2, NH\u2014SO2\u2014CH3, NH\u2014SO2\u2014C2H5, \u2550O, CF3, (CH2)\u2014 methoxy, methoxy, NH\u2014SO2\u2014CH\u2014(CH3)2, \u2014(CH2)\u2014O\u2014(CH2)2-methoxy, \u2014O\u2014CH\u2014(CH3)2;
R2 is selected from Cl, and F;
R3 is hydrogen;
R5 is selected from hydrogen, F, and Cl;
R6 is selected from hydrogen, F, and Cl;
R7 is selected from hydrogen, F, and Cl;
L is selected from C0-3-alkylene, \u2014CD2-, and C3-8 branched alkylene;
R8 is selected from hydrogen, and methyl; and
R9 is selected from \u2014(CH2)\u2014 pyridyl, benzyl, CD2-tetrahydro-pyran, tetrahydro-pyran, tetrahydro-thiopyran 1,1-dioxide, piperidinyl, pyrrolidine-2-one, dioxane, cyclopropyl, tetrahydrofuran, cyclohexyl, and cycloheptyl, wherein said groups are optionally substituted with one to three substituents each independently selected from F, OCHF2, CO-methyl, OH, methyl, methoxy, CN, ethyl, and NH\u2014CO-methyl.
7. A compound of claim 1, wherein:
R1 is selected from piperidinyl, morpholinyl, pyrrolidinyl, azepane, and 1,4-oxazepane, wherein said R1 groups are each independently optionally substituted with one to three substituents selected from F, methyl, CF3, ethyl, fluoro-ethyl, trifluoro-ethyl, \u2014(CH2)2-methoxy, \u2014(CH2)-methoxy, methoxy, \u2550O, \u2014(CH2)\u2014O\u2014(CH2)2-methoxy, and \u2014O\u2014CH\u2014(CH3)2;
R2 is Cl;
R3 is hydrogen;
R5 is selected from hydrogen, F, and Cl;
R6 is selected from hydrogen, F, and Cl;
R7 is selected from hydrogen, F, and Cl;
L is selected from \u2014CH2\u2014, and \u2014CD2-;
R8 is selected from hydrogen, and methyl; and
R9 is selected from pyridyl, benzyl, tetrahydro-pyran, dioxane, and tetrahydrofuran, wherein said groups are optionally substituted with one to three substituents each independently selected from F, OH, methyl, ethyl, methoxy, and CN.
8. (canceled)
9. A compound selected from:
(R)-Piperidine-3-carboxylic acid (5-chloro-4-{3-(tetrahydro-pyran-4-ylmethyl)-amino-phenyl}-pyridin-2-yl)-amide;
(S)-Piperidine-3-carboxylic acid (5-chloro-4-{3-(tetrahydro-pyran-4-ylmethyl)-amino-phenyl}-pyridin-2-yl)-amide;
(R)-Piperidine-3-carboxylic acid (5-chloro-4-{3-fluoro-5-(tetrahydro-pyran-4-ylmethyl)-amino-phenyl}-pyridin-2-yl)-amide;
(R)-3-(5-Chloro-4-{3-fluoro-5-(tetrahydro-pyran-4-ylmethyl)-amino-phenyl}-pyridin-2-ylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester;
(S)-Piperidine-3-carboxylic acid (5-chloro-4-{3-fluoro-5-(tetrahydro-pyran-4-ylmethyl)-amino-phenyl}-pyridin-2-yl)-amide;
(R)-Piperidine-3-carboxylic acid (5-chloro-4-{2-fluoro-5-(tetrahydro-pyran-4-ylmethyl)-amino-phenyl}-pyridin-2-yl)-amide;
(R)-Piperidine-3-carboxylic acid (5-chloro-4-{4-chloro-3-(tetrahydro-pyran-4-ylmethyl)-amino-phenyl}-pyridin-2-yl)-amide;
Morpholine-2-carboxylic acid (5-chloro-4-{3-fluoro-5-(tetrahydro-pyran-4-ylmethyl)-amino-phenyl}-pyridin-2-yl)-amide; and
(R)-Morpholine-2-carboxylic acid (5-chloro-4-{2-fluoro-5-(tetrahydro-pyran-4-ylmethyl)-amino-phenyl}-pyridin-2-yl)-amide;
and pharmaceutically acceptable salts thereof.
10. (canceled)
11. (canceled)
12. A method of treatment of a disease or condition mediated by CDK9 comprising administration to a subject in need thereof a therapeutically effective amount of a compound according to claim 1, or a pharmaceutically acceptable salt thereof.
13. A pharmaceutical composition comprising a compound according to claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, diluent or excipient.
14. A compound of claim 1, which is selected from the group consisting of:
and the pharmaceutically acceptable salts thereof.
15. A compound of claim 1, which is selected from the group consisting of:
and the pharmaceutically acceptable salts thereof.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. A compound, having the structure:
wherein
M is a metal having an atomic weight greater than 40;
(C\u2014N) is a substituted or unsubstituted cyclometallated ligand, and (C\u2014N) is different from at least one other ligand attached to the metal;
each R8, R10, and R12 to R14 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF3, NO2, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group;
additionally or alternatively, any two adjacent substituted positions together form, independently, a fused 4- to 7-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the 4- to 7-member cyclic group may be optionally substituted with a substituent independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF3, NO2, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group;
m has a value of at least 1;
n has a value of at least 1; and
m+n is the maximum number of ligands that may be attached to the metal.
2. The compound of claim 1, wherein n is 2.
3. The compound of claim 2, wherein each ligand is organometallic.
4. The compound of clam 1, wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, or Ag.
5. The compound of claim 4, wherein M is Ir.
6. The compound of claim 1, wherein at least one of R8, R10, R12 to R14, and a substituent of (C\u2014N) is independently selected from substituted or unsubstituted phenyl, napthyl, or pyridyl.
7. The compound of claim 6, wherein at least one of R8, R10, R12 to R14, and a substituent of (C\u2014N) is phenyl.
8. The compound of claim 7, wherein the compound has a structure selected from the group consisting of:
wherein X is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF3, NO2, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group;
additionally or alternatively, any two adjacent substituted positions together form, independently, a fused 4- to 7-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the 4- to 7-member cyclic group may be further substituted by substituent X; and
R9 and R11 are F.
9. The compound of claim 1, wherein the compound has a structure selected from the group consisting of:
wherein X is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF3, NO2, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group;
additionally or alternatively, any two adjacent substituted positions together form, independently, a fused 4- to 7-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the 4- to 7-member cyclic group may be further substituted by substituent X; and
R9 and R11 are F.
10. The compound of claim 1, wherein the compound has a structure selected from the group consisting of:
wherein X is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF3, NO2, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group;
additionally or alternatively, any two adjacent substituted positions together form, independently, a fused 4- to 7-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the 4- to 7-member cyclic group may be further substituted by substituent X;
Z is selected from \u2014CH2, \u2014CRR, \u2014NH, \u2014NR, \u2014O, \u2014S, \u2014SiR wherein R is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF3, NO2, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group; and
R9 and R11 are F.
11. The compound of claim 1, wherein the compound is a phosphorescent emissive material.
12. The compound of claim 1, wherein at least one ligand is a phosphorescent emissive ligand at room temperature and at least one ligand is not a phosphorescent emissive ligand at room temperature.
13. The compound of claim 12, wherein the ligand emissive in the compound at room temperature has a triplet energy corresponding to a wavelength that is at least 80 nm greater than the wavelength corresponding to the triplet energy of the ligand that is not emissive in the compound at room temperature.
14. The compound of claim 13, wherein the emissive ligand is organometallic.
15. The compound of claim 13, wherein the emissive ligand has a triplet energy corresponding to a wavelength of 500-520 nm.
16. The compound of claim 13, wherein the emissive ligand has a triplet energy corresponding to a wavelength greater than 590 nm.
17. The compound of claim 13, wherein each ligand is organometallic.
18. The compound of claim 17, wherein the emissive ligand has a triplet energy corresponding to a wavelength of 500-520 nm.
19. The compound of claim 17, wherein the emissive ligand has a triplet energy corresponding to a wavelength of 590 nm.
20. A compound, having the structure:
wherein
M is Ir;
(C\u2014N) is a substituted or unsubstituted cyclometallated ligand, and (C\u2014N) is different from at least one other ligand attached to the metal;
each R8, R10, and R12 to R14 are H;
m has a value of at least 1;
n has a value of at least 1; and
m+n is the maximum number of ligands that may be attached to the metal.
21. The compound of claim 20, wherein n is 2 and m is 1.
22. The compound of claim 21, having the structure:
23. The compound of claim 21, having the structure:
24. The compound of claim 21, having the structure:
25. The compound of claim 21, having the structure:
26. The compound of claim 21, having the structure:
27. The compound of claim 21, having the structure:
28. An organic light emitting device, comprising:
(a) an anode;
(b) a cathode; and
(c) an emissive layer disposed between and electrically connected to the anode and the cathode, the emissive layer further comprising a compound having the structure
\u2003wherein
M is a metal having an atomic weight greater than 40;
(C\u2014N) is a substituted or unsubstituted cyclometallated ligand, and (C\u2014N) is different from at least one other ligand attached to the metal;
each R8, R10, and R12 to R14 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF3, NO2, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group;
additionally or alternatively, any two adjacent substituted positions together form, independently, a fused 4- to 7-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the 4- to 7-member cyclic group may be optionally substituted with a substituent independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF3, NO2, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group;
m has a value of at least 1;
n has a value of at least 1; and
m+n is the maximum number of ligands that may be attached to the metal.
29. The device of claim 28, wherein n is 2.
30. The device of claim 29, wherein each ligand is organometallic.
31. The device of clam 28, wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, or Ag.
32. The device of claim 31, wherein M is Ir.
33. The device of claim 28, wherein at least one of R8, R10, R12 to R14, and a substituent of (C\u2014N) is independently selected from substituted or unsubstituted phenyl, napthyl, or pyridyl.
34. The device of claim 33, wherein at least one of R8, R10, R12 to R14, and a substituent of (C\u2014N) is phenyl.
35. The device of claim 34, wherein the compound has a structure selected from the group consisting of:
wherein X is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF3, NO2, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group;
additionally or alternatively, any two adjacent substituted positions together form, independently, a fused 4- to 7-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the 4- to 7-member cyclic group may be further substituted by substituent X; and
R9 and R11 are F.
36. The device of claim 28, wherein the compound has a structure selected from the group consisting of:
wherein X is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF3, NO2, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group;
additionally or alternatively, any two adjacent substituted positions together form, independently, a fused 4- to 7-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the 4- to 7-member cyclic group may be further substituted by substituent X; and
R9 and R11 are F.
37. The device of claim 28, wherein the compound has a structure selected from the group consisting of:
wherein X is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF3, NO2, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group;
additionally or alternatively, any two adjacent substituted positions together form, independently, a fused 4- to 7-member cyclic group, wherein said cyclic group is cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl, and wherein the 4- to 7-member cyclic group may be further substituted by substituent X;
Z is selected from \u2014CH2, \u2014CRR, \u2014NH, \u2014NR, \u2014O, \u2014S, \u2014SiR wherein R is independently selected from hydrogen, alkyl, alkenyl, alkynyl, alkylaryl, CN, CF3, NO2, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group; and
R9 and R11 are F.
38. The device of claim 28, wherein the compound is a phosphorescent emissive material.
39. The device of claim 28, wherein at least one ligand is a phosphorescent emissive ligand in the compound at room temperature and at least one ligand is not a phosphorescent emissive ligand at room temperature.
40. The device of claim 39, wherein the ligand emissive in at room temperature in the compound has a triplet energy corresponding to a wavelength that is at least 80 nm greater than the wavelength corresponding to the triplet energy of the ligand that is not emissive in the compound at room temperature.
41. The device of claim 40, wherein the emissive ligand is organometallic.
42. The device of claim 40, wherein the emissive ligand has a triplet energy corresponding to a wavelength of 500-520 nm.
43. The device of claim 40, wherein the emissive ligand has a triplet energy corresponding to a wavelength greater than 590 nm.
44. The organic light emitting device of claim 40, wherein each ligand is organometallic.
45. The device of claim 44, wherein the emissive ligand has a triplet energy corresponding to a wavelength of 500-520 nm.
46. The device of claim 44, wherein the emissive ligand has a triplet energy corresponding to a wavelength greater than 590 nm.
47. The device of claim 44, wherein the device is incorporated into a consumer product.
48. An organic light emitting device, comprising:
(a) an anode;
(b) a cathode; and
(c) an emissive layer disposed between and electrically connected to the anode and the cathode, the emissive layer further comprising a compound having the structure
\u2003wherein
M is Ir;
(C\u2014N) is a substituted or unsubstituted cyclometallated ligand, and (C\u2014N) is different from at least one other ligand attached to the metal;
each R8, R10, and R12 to R14 are H;
m has a value of at least 1;
n has a value of at least 1; and
m+n is the maximum number of ligands that may be attached to the metal.
49. The device of claim 48, wherein n is 2 and m is 1.
50. The device of claim 49, wherein the compound has the structure:
51. The device of claim 49, wherein the compound has the structure:
52. The device of claim 49, wherein the compound has the structure:
53. The device of claim 49, wherein the compound has the structure:
54. The device of claim 49, wherein the compound has the structure:
55. The device of claim 49, wherein the compound has the structure: