Back to results
US 11,444,249 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsHsiao-Fan Chen, Tongxiang (Aaron) Lu, Nicholas J. Thompson, Eric A. Margulies, George Fitzgerald, Jerald Feldman
Life of this patent
Estimating the term…
Abstract
Compounds that are organic radicals that can have a dual function. The compounds can be fluorescent emitters that emit in the near-IR. The compounds can also facilitate reverse intersystem crossing (RISC) to convert triplet excitons in an OLED to singlet excited states to maximize utilization of generated excitons in the OLED and approach 100% internal quantum efficiency.
Claims20
A compound selected from the group consisting of Formulae BB, BC, BD, BE, BF, and BG
- wherein
- X1 to X5 are independently selected from CRA or N;
- X6 to X10 are independently selected from CRB or N;
- X11 to X15 are independently selected from CRC or N;
- X16 to X23 are independently selected from CRD or N;
- X24 to X31 are independently selected from CRE or N;
- RA, RB, RC, RD, and RE independently represent mono to the maximum allowable substitution, or no substitution;
- each R1 to R5, RA, RB, RC, RD, and RE are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- or optionally, any two adjacent R1 to R4, or any two adjacent RA, RB, RC, RD, and RE, can join to form a ring;
- RN is independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, and combinations thereof;
- wherein at least one of R1 to R5, RA, RB, RC, RD, or RE includes a polycyclic group selected from the group consisting of:
- and any aza-analogue of each thereof, each of which is optionally substituted with RP, wherein RP is selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, amino, aryl, heteroaryl, silyl, nitrile, and combinations thereof;
- wherein RF to RI independently represent mono to the maximum allowable substitution, or no substitution and are independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, amino, aryl, heteroaryl, silyl, and nitrile and combinations thereof;
- and
- Z and Z1 are independently selected from the group consisting of O, S, Se, NRN, CR′R″, SiR′R″, and GeR′R″, wherein R′ and R″ are independently RN;
- with the proviso that R5 in BD does not include both a pyrazole group and a pyrene group;
- with the proviso that, in Formula BB, X1 and X5 are not CRA, wherein RA is halide, at the same time;
- and
- with the proviso that, in Formula BE,
- at least one of X1 to X5 is CRA, wherein RA is selected from the group consisting of
- and any aza-analogue of each thereof, each of which is optionally substituted with RP, wherein RP is selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, amino, aryl, heteroaryl, silyl, nitrile, and combinations thereof.
18 more elements
An organic light emitting device (OLED) comprising:
- an anode;
- a cathode;
- and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound selected from the group consisting of:
- wherein
- X1 to X5 are independently selected from CRA or N;
- X6 to X10 are independently selected from CRB or N;
- X11 to X15 are independently selected from CRC or N;
- X16 to X23 are independently selected from CRD or N;
- X24 to X31 are independently selected from CRE or N;
- RA, RB, RC, RD, and RE independently represent mono to the maximum allowable substitution, or no substitution;
- each R1 to R5, RA, RB, RC, RD, and RE are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- or optionally, any two adjacent R1 to R4, or any two adjacent RA, RB, RC, RD, and RE, can join to form a ring;
- RN is independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, and combinations thereof;
- wherein at least one of R1 to R5, RA, RB, RC, RD, or RE includes a polycyclic group selected from the group consisting of:
- and any aza-analogue of each thereof, each of which is optionally substituted with RP, wherein RP is selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, amino, aryl, heteroaryl, silyl, nitrile, and combinations thereof;
- wherein RF to RI are independently selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, amino, aryl, heteroaryl, silyl, nitrile, and combinations thereof;
- and
- Z and Z1 are independently selected from the group consisting of O, S, Se, NRN, CR′R″, SiR′R″, and GeR′R″, wherein R′ and R″ are independently RN;
- with the proviso that, in Formula BB, X1 and X5 are not CRA, wherein RA is halide, at the same time;
- and
- with the proviso that, in Formula BE at least one of X1 to X5 is CRA, wherein RA is selected from the group consisting of
- and any aza-analogue of each thereof, each of which is optionally substituted with RP, wherein RP is selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, amino, aryl, heteroaryl, silyl, nitrile, and combinations thereof.
19 more elements
A compound of formula A-L-B:
- wherein Component A is a fluorescent emitter with at least one aromatic ring;
- Component B is a compound selected from the group consisting of Formulae BB, BC, BD, BE, BF, BG, B1, B2 and B10:
- wherein
- X1 to X5 are independently selected from CRA or N;
- X6 to X10 are independently selected from CO or N;
- X11 to X15 are independently selected from CRC or N;
- X16 to X23 are independently selected from CRD or N;
- X24 to X31 are independently selected from CRE or N;
- RA, RB, RC, RD, and RE independently represent mono to the maximum allowable substitution, or no substitution;
- each R1 to R5, RA, RB, RC, RD, and RE are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- or optionally, any two adjacent R1 to R4, or any two adjacent RA, RB, RC, RD, and RE, can join to form a ring;
- RN is independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, and combinations thereof;
- wherein at least one of R1 to R5, RA, RB, RC, RD, and RE includes a polycyclic group selected from the group consisting of:
- and any aza-analogue of each thereof, each of which is optionally substituted with RP, wherein RP is selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, amino, aryl, heteroaryl, silyl, nitrile, and combinations thereof;
- wherein RF to RI are independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, amino, aryl, heteroaryl, silyl, and nitrile;
- and
- Z and Z1 are independently selected from the group consisting of O, S, Se, NRN, CR′CR″, SiR′R″, and GeR′R″, wherein R′ and R″ are independently RN;
- with the proviso that the following compound is excluded
- and
- L is a direct bond or an organic linker;
- wherein L, if not a direct bond, is positioned at an aromatic ring carbon of Component A, or if L is a direct bond, then Component B is positioned at an aromatic ring carbon of Component A.
18 more elements
Dependencies are inferred from the claim text.