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US 10,256,419 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsJason Brooks, Geza Szigethy, Glenn Morello, Jun Deng, Peter I. Djurovich, Hsiao-Fan Chen
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Abstract
Imidazophenanthridine ligands and metal complexes are provided. The compounds exhibit improved stability through a linking substitution that links a nitrogen bonded carbon of an imidizole ring to a carbon on the adjacent fused aryl ring. The compounds may be used in organic light emitting devices, particularly as emissive dopants, providing devices with improved efficiency, stability, and manufacturing. In particular, the compounds provided herein may be used in blue devices having high efficiency.
Claims19
A compound having a structure (LA)nMLm according to Formula 1:
- wherein M is a metal having an atomic weight greater than 40, n has a value of at least 1 and m+n is the maximum number of ligands that may be attached to the metal;
- wherein A is a linking group selected from the group consisting of CR′R″CR′R″—, —CR′R′—CR″R″—, —CH2—CH2—, —CR′R′—CR′R′—CR′R′—, —CR′R″—NR′—, —CR′═CR′—CR′R′—, —O—SiR′R′—, —CR′R″—S—, —CR′R″—O—, and —CR′R″—SiR′R′—,
- wherein each R′ is independently selected from the group consisting of H, D, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof,
- wherein each R″ is independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof,
- wherein R′s and R″s are optionally connected to form a saturated five membered ring or a saturated six membered ring, and combinations thereof,
- wherein R1a to R1g are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, CN, CF3, CO2R, C(O)R, C(O)NR2, NR2, NO2, OR, SR, SO2, SOR, SO3R, halo, aryl, heteroaryl, a heterocyclic group, and combinations thereof;
- wherein each R is independently selected from the group consisting of hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, aryl, heteroaryl, and combinations thereof,
- wherein any one of the ring atoms to which R1b to R1g are attached may be replaced with a nitrogen atom, wherein when the ring atom is replaced with a nitrogen atom the corresponding R group is not present;
- wherein L is a substituted or unsubstituted cyclometallated ligand, wherein L can be joined to R1g through a linking group L2;
- wherein L2 is selected from the group consisting of a single bond, BR, NR, PR, O, S, Se, C—O, S—O, SO2, CR1R2, SiR′R2, and GeR1R2,
- wherein R1 and R2 can be same or different, and are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;
- wherein any adjacent R1 and R2 are optionally connected to form a saturated five membered ring or a saturated six membered ring.
9 more elements
An organic light emitting device (OLED) comprising:
- an anode;
- a cathode;
- an organic layer disposed between the anode and the cathode, wherein the organic layer comprising a compound having a structure (LA)nMLm according to Formula 1:
- wherein M is a metal having an atomic weight greater than 40, n has a value of at least land m+n is the maximum number of ligands that may be attached to the metal;
- wherein A is a linking group selected from the group consisting of —CR′R″—CR′R″—, —CR′R′—CR″R″—, —CH2—CH2—, —CR′R′—CR′R′—CR′R′—, —CR′R″—NR′—, —CR′═CR′—CR′R′—, —O—SiR′R′—, —CR′R″—S—, —CR′R″—O—, and —CR′R″—SiR′R′—,
- wherein each R′ is independently selected from the group consisting of H, D, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof,
- wherein each R″ is independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof,
- wherein R′s and R″s are optionally connected to form a saturated five membered ring or a saturated six membered ring, and combinations thereof,
- wherein R1a to R1g are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, CN, CF3, CO2R, C(O)R, C(O)NR2, NR2, NO2, OR, SR, SO2, SOR, SO3R, halo, aryl, heteroaryl, a heterocyclic group, and combinations thereof;
- wherein each R is independently selected from the group consisting of hydrogen, deuterium, halo, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, aryl, heteroaryl, and combinations thereof;
- wherein any one of the ring atoms to which R1b to R1g are attached may be replaced with a nitrogen atom, wherein when the ring atom is replaced with a nitrogen atom the corresponding R group is not present;
- wherein L is a substituted or unsubstituted cyclometallated ligand,
- wherein L can be joined to R1g through a linking group L2;
- wherein L2 is selected from the group consisting of a single bond, BR, NR, PR, O, S, Se, C—O, S—O, SO2, CR1R2, SiR1R2, and GeR1R2;
- wherein R1 and R2 can be same or different, and are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof;
- wherein any adjacent R1 and R2 are optionally connected to form a saturated five membered ring or a saturated six membered ring.
13 more elements
Dependencies are inferred from the claim text.