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US 10,854,826 B2Granted
Organic electroluminescent compounds, compositions and devices
AssigneeUniversal Display Corporation
InventorsJui-Yi Tsai, Alexey Borisovich Dyatkin, Pierre-Luc T. Boudreault, Walter Yeager, Chuanjun Xia
Life of this patent
Estimating the term…
Abstract
An OLED including an organic layer that contains metal complex compounds that are useful as a phosphorescent emitter is disclosed. The metal complex compounds include ligands that incorporate fluorinated side chains and has at least one substituent R selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof, wherein R is directly bonded to an aromatic ring. In the compound, C having an F attached thereto is separated by at least one carbon atom from the aromatic ring.
Claims20
A composition comprising a first compound;
- wherein the first compound is capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature;
- wherein the first compound has at least one aromatic ring and at least one substituent R;
- wherein each of the at least one R is independently selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof;
- wherein each of the at least one R is directly bonded to one of the aromatic rings;
- wherein in each of the at least one R, any C having an F attached thereto is separated by at least one carbon atom from the aromatic ring;
- wherein the first compound has the formula of M(L1)x(L2)y(L3)z;
- wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu;
- wherein x is 1, 2, or 3;
- wherein y is 0, 1, or 2;
- wherein z is 0, 1, or 2;
- wherein x+y+z is the oxidation state of the metal M;
- wherein when L1, L2, and L3 are each present, at least one of L1, L2, and L3 is different from the others;
- wherein L1, L2, and L3 are each independently selected from the group consisting of:
- wherein when one or both of L2 or L3 are present, L2 or L3 each can independently be
- wherein each X1 to X13 are independently selected from the group consisting of carbon and nitrogen;
- wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
- wherein R′ and R″ are optionally fused or joined to form a ring;
- wherein each Ra, Rb, Rc, and Rd may represent from a mono substitution to a maximum possible number of substitutions, or no substitution;
- wherein each of R′, R″, Ra, Rb, Rc, and Rd is 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 wherein any two adjacent substituents of Ra, Rb, Rc, and Rd are optionally fused or joined to form a ring or form a multidentate ligand;
- and
- wherein L1 comprises an R of the at least one substituent R.
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, comprising a first compound;
- wherein the first compound is capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature;
- wherein the first compound has at least one aromatic ring and at least one substituent R;
- wherein each of the at least one R is independently selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof;
- wherein each of the at least one R is directly bonded to one of the aromatic rings;
- wherein in each of the at least one R, any C having an F attached thereto is separated by at least one carbon atom from the aromatic ring;
- wherein the first compound has the formula of M(L1)x(L2)y(L3)z;
- wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu;
- wherein x is 1, 2, or 3;
- wherein y is 0, 1, or 2;
- wherein z is 0, 1, or 2;
- wherein x+y+z is the oxidation state of the metal M;
- wherein when L1, L2, and L3 are each present, at least one of L1, L2, and L3 is different from the others;
- wherein L1, L2, and L3 are each independently selected from the group consisting of:
- wherein when one or both of L2 or L3 are present, L2 or L3 each can independently be
- wherein each X1 to X13 are independently selected from the group consisting of carbon and nitrogen;
- wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
- wherein R′ and R″ are optionally fused or joined to form a ring;
- wherein each Ra, Rb, Rc, and Rd represents from a mono substitution to a maximum possible number of substitutions, or no substitutions;
- wherein each of R′, R″, Ra, Rb, Rc, and Rd is 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;
- wherein any two adjacent substituents of Ra, Rb, Rc, and Rd are optionally fused or joined to form a ring or form a multidentate ligand;
- and
- wherein L1 comprises an R of the at least one substituent R.
23 more elements
A consumer product comprising an organic light-emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an organic layer, disposed between the anode and the cathode, comprising a first compound;
- wherein the first compound is capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature;
- wherein the first compound has at least one aromatic ring and at least one substituent R;
- wherein each of the at least one R is independently selected from the group consisting of partially fluorinated alkyl, partially fluorinated cycloalkyl, and combinations thereof;
- wherein each of the at least one R is directly bonded to one of the aromatic rings;
- wherein in each of the at least one R, any C having an F attached thereto is separated by at least one carbon atom from the aromatic ring;
- wherein the first compound has the formula of M(L1)x(L2)y(L3)z;
- wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu;
- wherein x is 1, 2, or 3;
- wherein y is 0, 1, or 2;
- wherein z is 0, 1, or 2;
- wherein x+y+z is the oxidation state of the metal M;
- wherein when L1, L2, and L3 are each present, at least one of L1, L2, and L3 is different from the others;
- wherein L1, L2, and L3 are each independently selected from the group consisting of:
- wherein when one or both of L2 or L3 are present, L2 or L3 each can independently be
- wherein each X1 to X13 are independently selected from the group consisting of carbon and nitrogen;
- wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
- wherein R′ and R″ are optionally fused or joined to form a ring;
- wherein each Ra, Rb, Rc, and Rd represents from a mono substitution to a maximum possible number of substitutions, or no substitutions;
- wherein each of R′, R″, Ra, Rb, Rc, and Rd is 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;
- wherein any two adjacent substituents of Ra, Rb, Rc, and Rd are optionally fused or joined to form a ring or form a multidentate ligand;
- and
- wherein L1 comprises an R of the at least one substituent R.
23 more elements
Dependencies are inferred from the claim text.