Carbene compounds and organic electroluminescent devices
AssigneeUniversity of Southern California
InventorsMark E. THOMPSON, Peter I. DJUROVICH, Rasha HAMZE, Shuyang SHI, Moon Chul JUNG
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Abstract
A compound selected from the group consisting of Formula I, Formula II, and Formula III, wherein ring A, ring B, and ring C are independently a five-membered or six-membered, carbocyclic or heterocyclic ring, each of which is optionally aromatic; ring W of Formula I is a 6-membered heterocyclic ring, and ring W of Formula II or Formula III is a 5-membered or 6-membered heterocyclic ring; L is a monodentate ligand with a metal coordinating member selected from the group consisting of C, N, O, S, and P; and M is a metal selected from the group consisting of Cu, Au, and Ag.
Claims20
A compound selected from the group consisting of Formula I, Formula II, and Formula III,
- wherein
- ring A, ring B, and ring C are independently a five-membered or six-membered, carbocyclic or heterocyclic ring, each of which is optionally aromatic;
- ring W of Formula I is a 6-membered heterocyclic ring, and ring W of Formula II or Formula III is a 5-membered or 6-membered heterocyclic ring;
- L is a monodentate ligand with a coordinating member selected from the group consisting of C, N, O, S, and P;
- M is a metal selected from the group consisting of Cu, Au, and Ag;
- RA, RB, RC, and RW represent mono to the maximum allowable substitution, or no substitution, and each RA, RB, and RC is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof;
- or optionally, any two adjacent RA, RB, RC, or RW can join to form a ring, which is optionally substituted;
- and
- wherein for the compounds of Formula I, the two RW do not join to form a naphthalene fused to ring W;
- wherein the compounds of Formulae II and III do not include a carbene ligand A
- wherein
- ring Q is a five-membered or six-membered ring,
- RQ, RS and RT are independently selected from the group consisting of hydrogen, a C1-20 alkyl, and two RQ, or RS and RT, can join to form an optionally substituted saturated cyclic hydrocarbyl ring with an optional heteroatom;
- and
- RP is selected from an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted aryl, and an optionally substituted heteroaryl.
An organic electroluminescent device that includes an anode, a cathode, and an organic layer comprising a compound selected from the group consisting of Formula I, Formula II, and Formula III,
- wherein
- ring A, ring B, and ring C are independently a five-membered or six-membered, carbocyclic or heterocyclic ring, each of which is optionally aromatic;
- ring W of Formula I is a 6-membered heterocyclic ring, and ring W of Formula II or Formula III is a 5-membered or 6-membered heterocyclic ring;
- L is a monodentate ligand with a coordinating member selected from the group consisting of C, N, O, S, and P;
- M is a metal selected from the group consisting of Cu, Au, and Ag;
- RA, RB, RC, and RW represent mono to the maximum allowable substitution, or no substitution, and each RA, RB, and RC is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof;
- or optionally, any two adjacent RA, RB, RC, or RW can join to form a ring, which is optionally substituted;
- and
- wherein for the compounds of Formula I, the two RW do not join to form a naphthalene fused to ring W;
- wherein the compounds of Formulae II and III do not include a carbene ligand A
- wherein
- ring Q is a five-membered or six-membered ring,
- RQ, RS and RT are independently selected from the group consisting of hydrogen, a C1-20 alkyl, and two RQ, or RS and RT, can join to form an optionally substituted saturated cyclic hydrocarbyl ring with an optional heteroatom.
A consumer product comprising an organic light-emitting device (OLED), the OLED including an anode, a cathode, and an organic layer comprising a compound selected from the group consisting of Formula I, Formula II, and Formula III,
- wherein
- ring A, ring B, and ring C are independently a five-membered or six-membered, carbocyclic or heterocyclic ring, each of which is optionally aromatic;
- ring W of Formula I is a 6-membered heterocyclic ring, and ring W of Formula II or Formula III is a 5-membered or 6-membered heterocyclic ring;
- L is a monodentate ligand with a metal coordinating member selected from the group consisting of C, N, O, S, and P;
- M is a metal selected from the group consisting of Cu, Au, and Ag;
- RA, RB, RC, and RW represent mono to the maximum allowable substitution, or no substitution, and each RA, RB, and RC is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof;
- or optionally, any two adjacent RA, RB, RC, or RW can join to form a ring, which is optionally substituted;
- and
- wherein for the compounds of Formula I, the two RW do not join to form a naphthalene fused to ring W;
- wherein the compounds of Formulae II and III do not include a carbene ligand A
- wherein
- ring Q is a five-membered or six-membered ring,
- RQ, RS and RT are independently selected from the group consisting of hydrogen, a C1-20 alkyl, and two RQ, or RS and RT, can join to form an optionally substituted saturated cyclic hydrocarbyl ring with an optional heteroatom;
- and
- RP is selected from an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted aryl, and an optionally substituted heteroaryl;
- wherein the compounds of Formula I, Formula II, and Formula III are vapor deposited with a host material to provide the organic layer;
- wherein the consumer product is selected from the group consisting of a flat panel display, a computer monitor, a medical monitors television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display, a 3-D display, a virtual reality or augmented reality display, a vehicle, a large area wall, a theater or stadium screen, a light therapy device, and a sign.
Dependencies are inferred from the claim text.