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US 12,234,251 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsHsiao-Fan Chen, Tyler Fleetham, Nicholas J. Thompson
Life of this patent
Estimating the term…
Abstract
Provided are multi-NBN host compounds. The compound has the structure of Formula I: Also provided are formulations comprising these multi-NBN host compounds. Further provided are OLEDs and related consumer products that utilize these multi-NBN host compounds.
Claims21
A compound having the structure of Formula I:
- wherein:
- A is a monocyclic or multicyclic ring system comprising one or more fused or unfused 5-membered or 6-membered carbocyclic or heterocyclic rings which can be further substituted;
- each R independently has a structure of Formula II:
- R is fused to two consecutive carbon atoms in A through the dashed lines;
- Z1 and Z2 are each independently selected from the group consisting of O, S, Se, and NAr5;
- Ar1, Ar2, Ar3, Ar4, and Ar5 are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring which can be further substituted;
- index n is 0, 1, or 2 with the proviso that when 1) Z1 is NAr5, and 2) Ar1, Ar2 and Ar5 are all 6-membered carbocyclic rings, then n is 1 or 2;
- or when Z1 is O, then n is 1 or 2;
- or
- if Z1 and/or Z2 is O, then Ar1-Ar4 are each 6-membered carbocyclic rings that may be substituted with a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, aryl, nitrile, and combinations thereof,
- if Z1 is NAr5, and Ar1, Ar2 and Ar5 are all 6-membered carbocyclic rings in which index n is 1 and Z2 is NAr5, then A is a monocyclic ring system or A is a multicyclic fused ring system;
- and
- any two adjacent Ar3 and Ar4 can be joined or fused to form a ring.
10 more elements
An organic light emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an organic layer disposed between the anode and the cathode,
- wherein the organic layer comprises a compound selected from the group consisting of Formula I and Formula III;
- wherein Formula I has the structure:
- A is a monocyclic or multicyclic ring system comprising one or more fused or unfused 5-membered or 6-membered carbocyclic or heterocyclic rings which can be further substituted;
- each R independently has a structure of Formula II:
- R is fused to two consecutive carbon atoms in A through the dashed lines;
- Z1 and Z2 are each independently selected from the group consisting of O, S, Se, and NAr5;
- Ar1, Ar2, Ar3, Ar4, and Ar5 are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring which can be further substituted;
- index n is 0, 1, or 2 with the proviso that when 1) Z1 is NAr5, and 2) Ar1, Ar2 and Ar5 are all 6-membered carbocyclic rings, then p is 1 or 2;
- or when Z1 is O, then n is 1 or 2;
- or
- if Z1 and/or Z2 is O, then Ar1-Ar4 are each 6-membered carbocyclic rings that may be substituted with a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, aryl, nitrile, and combinations thereof,
- if Z1 is NAr5, and Ar1, Ar2 and Ar5 are all 6-membered carbocyclic rings in which index n is 1 and Z2 is NAr5, then A is a monocyclic ring system or A is a multicyclic fused ring system;
- and
- any two adjacent A, Ar3, and Ar4 can be joined or fused to form a ring;
- wherein Formula III has the structure:
- each X may be the same or different and is C or N;
- D is a monocyclic or multicyclic ring system comprising one or more fused or unfused 5-membered or 6-membered carbocyclic or heterocyclic rings which can be further substituted;
- R′ comprise a structure of Formula IV:
- each X′ may be the same or different and is C or N;
- R′ is joined to a carbon atom in D through the dashed line;
- Z3 is selected from the group consisting of O, S, Se, and NAr8;
- Z4 is selected from the group consisting of O, S, and Se;
- RA and RB each independently represent zero, mono to the maximum allowable substitution;
- each RA and RB is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- Ar6, Ar7, and Ar8 are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring which can be further substituted;
- and
- index m is 1 or 2.
28 more elements
A compound selected from the group consisting of:
- Compound name
- Structure
- Compound I″-[(Ri″)(Rj″)(Rk″)], wherein i″ is an integer from 1 to 65 and j″, k″ are indepen- dently an integer from 1 to 60
- wherein Compound I″-[(R1)(R1)(R1)] to Compound I″-[(R65)(R60)(R60)] having the structure
- Compound II″-[(Ri″)(Rj″)(Rk″)], wherein i″ is an integer from 1 to 65 and j″, k″ are indepen- dently an integer from 1 to 60
- wherein Compound II″-[(R1)(R1)(R1)] to Compound II″-[(R65)(R60)(R60)] having the structure
- Compound III ″-[(Ri″)(Rj″)(Rk″)], wherein i″ is an integer from 1 to 65 and j″, k″ are indepen- dently an integer from 1 to 60
- wherein Compound III″-[(R1)(R1)(R1)] to Compound III″-[(R65)(R60)(R60)] having the structure
- Compound IV″-[(Ri″)(Rj″)], wherein i″ is an integer from 1 to 65 and j″ is an integer from 1 to 60
- wherein Compound IV″-[(R1)(R1)] to Compound IV″-[(R65)(R60)] having the structure
- Compound V″-[(Ri″)(Rj″)], wherein i″ is an integer from 1 to 65 and j″ is an integer from 1 to 60
- wherein Compound V″-[(R1)(R1)] to Compound V″-[(R65)(R60)] having the structure
- Compound VI″-[(Ri″)(Rj″)], wherein i″ is an integer from 1 to 65 and j″ is an integer from 1 to 60
- wherein Compound VI″-[(R1)(R1)] to Compound VI″-[(R65)(R60)] having the structure
- Compound VII″-[(Ri″)(Rj″)], wherein i″ is an integer from 1 to 65 and j″ is an integer from 1 to 60
- wherein Compound VII″-[(R1)(R1)] to Compound VII″-[(R65)(R60)] having the structure
- Compound VIII″- [(Ri″)(Rj″)(Rk″)], wherein i″ is an integer from 1 to 65 and j″, k″ are indepen- dently an integer from 1 to 60
- wherein Compound VIII″-[(R1)(R1)(R1)] to Compound VIII″-[(R65)(R60)(R60)] having the structure
- Compound IX″- [(Ri″)(Rj″)(Rk″)], wherein i″ is an integer from 1 to 65 and j″, k″ are independently an integer from 1 to 60
- wherein Compound IX″-[(R1)(R1)(R1)] to Compound IX″-[(R65)(R60)(R60)] having the structure
- Compound X″- [(Ri″)(Rj″)(Rk″)], wherein i″ is an integer from 1 to 65 and j″, k″ are indepen- dently an integer from 1 to 60
- wherein Compound X″-[(R1″)(R1)(R1)] to Compound X″-[(R65)(R60)(R60)] having the structure
- Compound XI″- [(Ri″)(Rj″)(Rk″)], wherein i″ is an integer from 1 to 65 and j″, k″ are indepen- dently an integer from 1 to 60
- wherein Compound XI″-[(R1)(R1)(R1)] to Compound XI″-[(R65)(R60)(R60)] having the structure
- Compound XII″- [(Ri″)(Rj″)(Rk″)], wherein i″ is an integer from 1 to 65 and j″, k″ are indepen- dently an integer from 1 to 60
- wherein Compound XII″-[(R1)(R1)(R1)] to Compound XII″-[(R65)(R60)(R60)] having the structure
- Compound XIII″- [(Ri″)(Rj″)(Rk″)], wherein i″ is an integer from 1 to 65 and j″, k″ are indepen- dently an integer from 1 to 60
- wherein Compound XIII″-[(R1)(R1)(R1)] to Compound XIII″-[(R65)(R60)(R60)] having the structure
- Compound XIV″- [(Ri″)(Rj″)(Rk″)], wherein i″ is an integer from 1 to 65 and j″, k″ are indepen- dently an integer from 1 to 60
- wherein Compound XIV″-[(R1)(R1)(R1)] to Compound XIV″-[(R65)(R60)(R60)] having the structure
- Compound XV″- [(Ri″)(Rj″)(Rk″)], wherein i″ is an integer from 1 to 65 and j″, k″ are independently an integer from 1 to 60
- wherein Compound XV″-[(R1)(R1)(R1)] to Compound XV″-[(R65)(R60)(R60)] having the structure
- Compound XVI″- [(Ri″)(Rj″)(Rk″)], wherein i″ is an integer from 1 to 65 and j″, k″ are independently an integer from 1 to 60
- wherein Compound XVI″-[(R1)(R1)(R1)] to Compound XVI″-[(R65)(R60)(R60)] having the structure
- Compound XVII″- [(Ri″)(Rj″)(Rk″)], wherein i″ is an integer from 1 to 65 and j″, k″ are independently an integer from 1 to 60
- wherein Compound XVII″-[(R1)(R1)(R1)] to Compound XVII″-[(R65)(R60)(R60)] having the structure
- where R1 to R65 have the following structures:
34 more elements
Dependencies are inferred from the claim text.