Organic light emitting materials and devices
First Claim
Patent Images
1. An emissive material represented by the structure:
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wherein M is a heavy metal with an atomic weight of greater than or equal to 40;
R3 is a substituent having a Hammett value greater than 0.6;
each of R2, R4, R5, and R′
3 through R′
6 are independently selected from the group consisting of H, halogens, CN, perfluoroalkyl, trifluorovinyl, NO2, CO2R, C(O)R, S(O)R, SO2R, SO3R, P(O)R, PO2R, PO3R, C≡
CR, alkyl, alkenyl, aryl, heteroaryl, OR, SR, NR2 (including cyclic-amino), and PR2 (including cyclic-phosphino), where R is hydrogen, an alkyl group, an aryl group or a heteroaryl group;
m is an integer between 1 and 4 and n is an integer between 1 and 3; and
, is a monoanionic non carbon coordinating ligand.
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Abstract
An organic light emitting device is provided. The device has an anode, a cathode, and an emissive layer disposed between the anode and the cathode, the emissive layer further comprising an emissive material having the structure:
wherein each of the variables are defined herein.
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Citations
73 Claims
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1. An emissive material represented by the structure:
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wherein M is a heavy metal with an atomic weight of greater than or equal to 40; R3 is a substituent having a Hammett value greater than 0.6; each of R2, R4, R5, and R′
3 through R′
6 are independently selected from the group consisting of H, halogens, CN, perfluoroalkyl, trifluorovinyl, NO2, CO2R, C(O)R, S(O)R, SO2R, SO3R, P(O)R, PO2R, PO3R, C≡
CR, alkyl, alkenyl, aryl, heteroaryl, OR, SR, NR2 (including cyclic-amino), and PR2 (including cyclic-phosphino), where R is hydrogen, an alkyl group, an aryl group or a heteroaryl group;m is an integer between 1 and 4 and n is an integer between 1 and 3; and
,is a monoanionic non carbon coordinating ligand. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11)
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12. A composition represented by the structure:
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wherein M is a heavy metal with an atomic weight of greater than or equal to 40; each of R2 through R5 and R′
3 through R′
6 are independently selected from the group consisting of H, halogens, CN, perfluoroalkyl, trifluorovinyl, NO2, CO2R, C(O)R, S(O)R, SO2R, SO3R, P(O)R, PO2R, PO3R, C≡
CR, alkyl, alkenyl, aryl, heteroaryl, OR, SR, NR2 (including cyclic-amino), and PR2 (including cyclic-phosphino), where R is hydrogen, an alkyl group, an aryl group or a heteroaryl group, wherein at least one of R3 and R5 is CN;m is an integer between 1 and 4 and n is an integer between 1 and 3;
is a monoanionic non carbon coordinating ligand; and
,wherein if neither R3 nor R5 is an electron donating group then R′
4 is an electron donating group.- View Dependent Claims (13, 14, 15, 16, 17, 18)
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19. A composition represented by the structure:
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wherein M is a heavy metal with an atomic weight of greater than or equal to 40; each of R2, R4, and R′
3 through R′
6 are independently selected from the group consisting of H, halogens, CN, perfluoroalkyl, trifluorovinyl, NO2, CO2R, C(O)R, S(O)R, SO2R, SO3R, P(O)R, PO2R, PO3R, C≡
CR, alkyl, alkenyl, aryl, heteroaryl, OR, SR, NR2 (including cyclic-amino), and PR2 (including cyclic-phosphino), where R is hydrogen, an alkyl group, an aryl group or a heteroaryl group;at least one of R3 and R5 is CN, and, where only one of R3 and R5 is CN, the other is selected from the group consisting of H, perfluoroalkyl, trifluorovinyl, NO2, CO2R, C(O)R, S(O)R, SO2R, SO3R, P(O)R, PO2R, PO3R, C≡
CR, and aryl and heteroaryl groups substituted with halogens, CN, perfluoroalkyl, trifluorovinyl, NO2, CO2R, C(O)R, S(O)R, SO2R, SO3R, P(O)R, PO2R, or PO3R, where R is a hydrogen, alkyl, aryl or heteroaryl group, wherein m is an integer between 1 and 4 and n is an integer between 1 and 3 and X-Y is non carbon coordinating monoamonic ligand. - View Dependent Claims (20, 21, 22, 23, 24, 25, 26)
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27. A light emitting device comprising an organic layer, the organic layer comprising a composition represented by the structure:
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wherein M is a heavy metal with an atomic weight of greater than or equal to 40; each of R2 through R5 and R′
3 through R′
6 are independently selected from the group consisting of H, halogens, CN, perfluoroalkyl, trifluorovinyl, NO2, CO2R, C(O)R, S(O)R, SO2R, SO3R, P(O)R, PO2R, PO3R, C≡
CR, alkyl, alkenyl, aryl, heteroaryl, OR, SR, NR2 (including cyclic-amino), and PR2 (including cyclic-phosphino), where R is hydrogen, an alkyl group, an aryl group or a heteroaryl group, wherein at least one of R3 and R5 is CN;one of R3 and R5 is optionally an electron donating group; m is an integer between 1 and 4 and n is an integer between 1 and 3; and
is a monoanionic non carbon coordinating ligand. - View Dependent Claims (28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38)
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39. A light emitting device comprising an organic layer, the organic layer comprising a composition represented by the structure:
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wherein M is a heavy metal with an atomic weight of greater than or equal to 40; each of R2 through R5 and R′
3 through R′
6 are independently selected from the group consisting of H, halogens, CN, perfluoroalkyl, trifluorovinyl, NO2, CO2R, C(O)R, S(O)R, SO2R, SO3R, P(O)R, PO2R, PO3R, C≡
CR, alkyl, alkenyl, aryl, heteroaryl, OR, SR, NR2 (including cyclic-amino), and PR2 (including cyclic-phosphino), where R is hydrogen, an alkyl group, an aryl group or a heteroaryl group, wherein at least one of R3 and R5 is CN;one of R3 and R5 is optionally an electron donating group; m is an integer between 1 and 4 and n is an integer between 1 and 3;
is a monoanionic non carbon coordinated ligand; and
,wherein if neither R3 nor R5 is an electron donating group then R′
4 is an electron donating group.- View Dependent Claims (40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50)
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51. A light emitting device comprising an organic layer, the organic layer comprising a composition represented by the structure:
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wherein M is a heavy metal with an atomic weight of greater than or equal to 40; each of R2, R4, and R′
3 through R′
6 are independently selected from the group consisting of H, halogens, CN, perfluoroalkyl, trifluorovinyl, NO2, CO2R, C(O)R, S(O)R, SO2R, SO3R, P(O)R, PO2R, PO3R, C≡
CR, alkyl, alkenyl, aryl, heteroaryl, OR, SR, NR2 (including cyclic-amino), and PR2 (including cyclic-phosphino), where R is hydrogen, an ailcyl group, an aryl group or a heteroaryl group;m is an integer between 1 and 4 and n is an integer between 1 and 3; and
,is a monoanionic non carbon coordinating ligand; at least one of R3 and R5 is CN, and where only one of R3 and R5 is CN, the other is selected from the group consisting of H, perfluoroalkyl, trifluorovinyl, NO2, CO2R, C(O)R, S(O)R, SO2R, SO3R, P(O)R, PO2R, PO3R, C≡
CR, and aryl and heteroaryl groups substituted with halogens, CN, perfluoroalkyl, trifluorovinyl, NO2, CO2R, C(O)R, S(O)R, SO2R, SO3R, P(O)R, PO2R, or PO3R, where R is a hydrogen, alkyl, aryl or heteroaryl group.- View Dependent Claims (52, 53, 54)
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55. A composition represented by the following structure:
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wherein M is a heavy metal with an atomic weight of greater than or equal to 40; each of R2 through R5 and R′
3 through R′
6 are independently selected from the group consisting of H, halogens, CN, perfluoroalkyl, trifluorovinyl, NO2, CO2R, C(O)R, S(O)R, SO2R, SO3R, P(O)R, PO2R, PO3R, C≡
CR, alkyl, alkenyl, aryl, heteroaryl, OR, SR, NR2 (including cyclic-amino), and PR2 (including cyclic-phosphino), where R is hydrogen, an alkyl group, an aryl group or a heteroaryl group, wherein at least one of R3 and R5 is CN;m is an integer between 1 and 4 and n is an integer between 1 and 3; and
,is a monoanionic non carbon coordinating ligand, wherein R3 and R5 are selected to provide a hypsochromic shift in the emission spectrum of the compound of greater than or equal to approximately 40 nm as compared with the emission spectrum of a composition with the following structure;
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56. An emissive material represented by the structure:
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wherein M is a heavy metal with an atomic weight of greater than or equal to 40;
m is at least 1 n is at least 0X-Y is an ancillary ligand; R2 and R4 are both F; each of R3, R5, and R′
3 through R′
6 are independently selected from the group consisting of H, halogens, CN, perfluoroalkyl, trifluorovinyl, NO2, CO2R, C(O)R, S(O)R, SO2R, SO3R, P(O)R, PO2R, PO3R, C≡
CR, alkyl, alkenyl, aryl, heteroaryl, OR, SR, NR2 (including cyclic-amino), and PR2 (including cyclic-phosphino), where R is hydrogen, an alkyl group, an aryl group or a heteroaryl group, wherein at least one of R3 and R5 is CN. - View Dependent Claims (57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71)
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72. A light emitting device comprising an organic layer, the organic layer comprising a composition represented by the general structure:
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wherein M is a heavy metal with an atomic weight of greater than or equal to 40;
m is at least 1 n is at least 0X-Y is an ancillary ligand; R2 and R4 are both F; each of R3, R5, and R′
3 through R′
6 are independently selected from the group consisting of H, halogens, CN, perfluoroalkyl, trifluorovinyl, NO2, CO2R, C(O)R, S(O)R, SO2R, SO3R, P(O)R, PO2R, PO3R, C≡
CR, alkyl, alkenyl, aryl, heteroaryl, OR, SR, NR2 (including cyclic-amino), and PR2 (including cyclic-phosphino), where R is hydrogen, an alkyl group, an aryl group or a heteroaryl group, wherein at least one of R3 and R5 is CN. - View Dependent Claims (73)
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Specification