MATERIALS FOR ORGANIC LIGHT EMITTING DIODE
Organometallic compounds comprising a phenylquinoline or phenylisoquinoline ligand having the quinoline or isoquinoline linked to the phenyl ring of the phenylquinoline or phenylisoquinoline, respectively, via two carbon atoms. These compounds also comprise a substituent other than hydrogen and deuterium on the quinoline, isoquinoline or linker. These compounds may be used as red emitters in phosphorescent OLEDs. In particular, these compounds may provide stable, narrow and efficient red emission.
1 . A compound having the formula M(L 1 ) x (L 2 ) y (L 3 ) z :
wherein the ligand L 1 is
wherein the ligand L 2 is
wherein the ligand L 3 is a third ligand;
wherein each L 1 , L 2 and L 3 can be the same or different;
wherein M is a metal having an atomic number greater than 40;
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 R is a carbocyclic or heterocyclic ring fused to the pyridine ring;
R is optionally further substituted with R′;
wherein A, B, and C are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein R′, R Z , R A , R B , and R C may represent mono, di, tri, or tetra substitutions;
wherein each of R 1 , R 2 , R 3 , R 4 , R′, R Z , R A , R B , and R C 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, sulfonyl, sulfonyl, phosphino, and combinations thereof;
wherein at least one of R 1 , R 2 , R 3 , R 4 , and R′ is not hydrogen or deuterium; and
wherein any two adjacent R 1 , R 2 , R 3 , R 4 , and R′ are optionally linked to form an alkyl ring.
2 . The compound of claim 1 , wherein M is Ir.
3 . The compound of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , and R′ is an alkyl.
4 . The compound of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , and R′ is an alkyl having more than 2 carbon atoms.
5 . The compound of claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , and R′ is isobutyl.
6 . The compound of claim 1 , wherein R′ is not hydrogen or deuterium.
7 . The compound of claim 1 , wherein L 3 is a monoanionic bidentate ligand.
8 . The compound of claim 1 , wherein L 3 is
and
wherein R′ 1 , R′ 2 , and R′ 3 are each 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, sulfanyl, sulfonyl, phosphino, and combinations thereof.
9 . The compound of claim 8 , wherein at least one of R′ 1 , R′ 2 , and R′ 3 contains a branched alkyl moiety with branching at a position further than the α position to the carbonyl group.
10 . The compound of claim 8 , wherein at least one of R′ 1 and R′ 3 is isobutyl.
11 . The compound of claim 8 , wherein R′ 2 is hydrogen.
12 . The compound of claim 1 , wherein the compound has the formula:
wherein R 5 and R 6 may represent mono, di, tri, or tetra substitutions;
wherein each of R 5 and R 6 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;
wherein at least one of R 1 , R 2 , R 3 , R 4 , and R 6 is not hydrogen or deuterium; and
wherein m is 1, 2, or 3.
13 . The compound of claim 1 , wherein the compound has the formula:
wherein R 5 and R 6 may represent mono, di, tri, or tetra substitutions;
wherein each of R 5 and R 6 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;
wherein at least one of R 1 , R 2 , R 3 , R 4 , and R 6 is not hydrogen or deuterium; and
wherein m is 1, 2, or 3.
14 . The compound of claim 1 , wherein the compound is homoleptic.
15 . The compound of claim 1 , wherein the compound is heteroleptic.
16 . The compound of claim 1 , wherein the compound is selected from the group consisting of:
17 . The compound of claim 1 , wherein the compound is selected from the group consisting of:
18 . A first device comprising a first organic light emitting device, further comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having the formula M(L 1 ) x (L 2 ) y (L 3 ) z :
wherein the ligand L 1 is
wherein the ligand L 2 is
wherein the ligand L 3 is a third ligand;
wherein each L 1 , L 2 and L 3 can be the same or different;
wherein M is a metal having an atomic number greater than 40;
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 R is a carbocyclic or heterocyclic ring fused to the pyridine ring;
R is optionally further substituted with R′;
wherein A, B, and C are each independently a 5 or 6-membered carbocyclic or heterocyclic ring;
wherein R′, R Z , R A , R B , and R C may represent mono, di, tri, or tetra substitutions;
wherein each of R 1 , R 2 , R 3 , R 4 , R′, R Z , R A , R B , and R C 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;
wherein at least one of R 1 , R 2 , R 3 , R 4 , and R′ is not hydrogen or deuterium; and
wherein any two adjacent R 1 , R 2 , R 3 , R 4 , and R′ are optionally linked to form an alkyl ring.
19 . The first device of claim 18 , wherein the first device is a consumer product.
20 . The first device of claim 18 , wherein the first device is an organic light emitting device.
21 . The first device of claim 18 , wherein the first device comprises a lighting panel.
22 . The first device of claim 18 , wherein the organic layer is an emissive layer and the compound is an emissive dopant.
23 . The first device of claim 18 , wherein the organic layer further comprises a host.
24 . The first device of claim 23 , wherein the host is a metal 8-hydroxyquinolate.