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US 2026/0231602 A1Published application
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsNoah Horwitz, Hsiao-Fan Chen, Tyler Fleetham, Joseph A. Macor, Suman Layek, Kevin G. Fowler
Life of this patent
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Abstract
Provided are organic compounds comprising at least two fused 6-membered rings wherein a same boron atom is part of both fused 6-membered rings and wherein at least one of the two fused 6-membered rings further contains a nitrogen atom. Also provided are formulations comprising these organic compounds. Further provided are organic light emitting devices (OLEDs) as well as related consumer products that utilize these organic compounds.
Claims20
A compound comprising a structure of Formula I:
- wherein moieties A, B, and C are each independently a monocyclic ring or fused polycyclic ring system, wherein the monocyclic ring or each ring of the polycyclic fused ring system is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- wherein Z is selected from the group consisting of O, S, NR′, BR′, CR′R″, SiR′R″, Se, BR′R″, PR′, C═O, C═NR′, N—C═O, N—C≡N, C═S, SO, SO2, P(O)R′, and GeR′R″;
- wherein RA, RB, and RC each independently represent mono to the maximum allowable substitution, or no substitution;
- wherein RN is selected from the group consisting of CN, BRB1RB2, BRB1RB2RB3, (C═O)R′″, (C═NRN*)R′″, SO2RS, (S═O)RS, (P═O)RP1RP2, F, CF3, imidazole, oxazole, thiazole, and substituted variants thereof,
- wherein each RN*, RS, RP1, RP2, R′, R″, R′″, RA, RB, and RC is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, chlorine, iodine, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, wherein each RB1, RB2, and RB3 is independently a substituent selected from the group consisting of deuterium, halogen, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,
- represents a single bond or a double bond;
- any two of RN*, RS, RP1, RP2, R′, R″, R′″, RA, RB, and RC may be joined or fused to form a ring;
- and
- with the proviso that the following four conditions are all true:
- (1) RN does not simultaneously form a ring with both an RA and an RB substituent;
- (2) when the compound comprises Formula Ia,
- then Z is selected from BR′, BR′R″, C═O, N—C═O, N—C≡N, and NR′ with the proviso that when Z is NR′, R′ is joined to RA to form a 6-10 membered ring or R′ is joined to RA to form a 5-membered ring comprising 2 or more heteroatoms;
- (3) when RN is (C═NRN*)R′″, RN* and R′″ do not join to form a 6-membered ring;
- and
- (4) wherein the compound does not comprise:
12 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 laver comprises the compound comprising a structure of Formula I:
- wherein moieties A, B, and C are each independently a monocyclic ring or fused polycyclic ring system, wherein the monocyclic ring or each ring of the polycyclic fused ring system is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- wherein Z is selected from the group consisting of O, S, NR′, BR′, CR′R″, SiR′R″, Se, BR′R″, PR′, C═O, C═NR′, N—C═O, N—C≡N, C═S, SO, SO2, P(O)R′, and GeR′R″;
- wherein RA, RB, and RC each independently represent mono to the maximum allowable substitution, or no substitution;
- wherein RN is selected from the group consisting of CN, BRB1RB2, BRB1RB2RB3, (C═O)R′″, (C═NRN*)R′″, SO2RS, (S═O)RS, (P═O)RP1RP2, F, CF3, imidazole, oxazole, thiazole, and substituted variants thereof,
- wherein each RN*, RS, RP1, RP2, R′, R″, R′″, RA, RB, and RC is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, chlorine, iodine, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein each RB1, RB2, and RB3 is independently a substituent selected from the group consisting of deuterium, halogen, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,
- represents a single bond or a double bond;
- any two of RN*, RS, RP1, RP2, R′, R″, R′″, RA, RB, and RC may be joined or fused to form a ring;
- and
- with the proviso that the following four conditions are all true:
- (1) RN does not simultaneously form a ring with both an RA and an RB substituent;
- (2) when the compound comprises Formula Ia,
- then Z is selected from BR′, BR′R″, C═O, N—C═O, N—C≡N, and NR′ with the proviso that when Z is NR′, R′ is joined to RA to form a 6-10 membered ring or R′ is joined to RA to form a 5-membered ring comprising 2 or more heteroatoms;
- (3) when RN is (C═NRN*)R′″, RN* and R′″ do not join to form a 6-membered ring;
- and
- (4) wherein the compound does not comprise:
18 more elements
A compound, or a neutral molecular form thereof, or a monovalent or polyvalent form thereof, or a monomeric or polymeric form thereof, or a macromolecular or supramolecular form thereof, wherein the compound has a structure of Formula I:
- wherein moieties A, B, and C are each independently a monocyclic ring or fused polycyclic ring system, wherein the monocyclic ring or each ring of the polycyclic fused ring system is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
- wherein Z is selected from the group consisting of O, S, NR′, BR′, CR′R″, SiR′R″, Se, BR′R″, PR′, C═O, C═NR′, N—C═O, N—C≡N, C═S, SO, SO2, P(O)R′, and GeR′R″;
- wherein RA, RB, and RC each independently represent mono to the maximum allowable substitution, or no substitution;
- wherein RN is selected from the group consisting of CN, BRB1RB2, BRB1RB2RB3, (C═O)R′″, (C═NRN*)R′″, SO2RS, (S═O)RS, (P═O)RP1RP2, F, CF3, imidazole, oxazole, thiazole, and substituted variants thereof,
- wherein each RN*, RS, RP1, RP2, R′, R″, R′″, RA, RB, and RC is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, chlorine, iodine, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, wherein each RB1, RB2, and RB3 is independently a substituent selected from the group consisting of deuterium, halogen, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof,
- represents a single bond or a double bond;
- any two substituents may be joined or fused to form a ring;
- and
- with the proviso that the following four conditions are all true:
- (1) RN does not simultaneously form a ring with both an RA and an RB substituent;
- (2) when the compound comprises Formula Ia,
- then Z is selected from BR′, BR′R″, C═O, N—C═O, N—C≡N, and NR′ with the proviso that when Z is NR′, R′ is joined to RA to form a 6-10 membered ring or R′ is joined to RA to form a 5-membered ring comprising 2 or more heteroatoms;
- (3) when RN is (C═NRN*)R′″, RN* and R′″ do not join to form a 6-membered ring;
- and
- (4) wherein the compound does not comprise:
12 more elements
Dependencies are inferred from the claim text.