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US 2026/0308168 A1Published application
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsRasha HAMZE, Sean Michael Ryno, Elena Sheina, Hsiao-Fan Chen, Dmitry Sergeyevich Andrianov, Kelly R. Lewis, Charles J. Stanton
Life of this patent
Estimating the term…
Abstract
Provided are organic compounds comprising a 6-membered carbocyclic ring to which four 5-membered heterocyclic rings each comprising exactly one nitrogen atom are fused. 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 of Formula I:
- wherein each of X1 to X16 is independently C or N;
- each of RA, RB, RC, and RD independently represents mono to the maximum allowable substitutions, or no substitutions;
- wherein any two of RA, RB, RC, and RD may be joined or fused to form a ring;
- with the proviso that, if the compound comprises a structure of Formula II:
- wherein each of X44 to X4 is independently C or N;
- wherein Y1 is selected from the group consisting of O, NRY1, and CMe2;
- wherein RE represents mono to the maximum allowable substitutions, or no substitutions;
- then
- (i) when Y1 is O or CMe2, then X15 is C, and
- (ii) when Y1 is NRY1, then RY1 and RE do not join to form a 5-membered ring;
- with the proviso that, if no two of RA, two of RB, two of RC, or two of RD are joined to form a ring, then at least one of RA, RB, RC, or RD comprises a structure selected from the group consisting of deuterium, alkyldiarylsilyl, dialkylarylsilyl, germyl, tetraphenylene, a bridged polycyclic ring, an alkyl or cycloalkyl comprising five or more carbons, and an aromatic ring fused by a non-aromatic ring;
- with the proviso that, if two of RA, two of RB, two of RC, or two of RD are joined to form a benzene ring, then at least one of RA, RB, RC, or RD comprises a structure selected from the group consisting of deuterium, silyl, germyl, tetraphenylene, benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (bimbim), a bridged polycyclic ring, an alkyl or cycloalkyl comprising five or more carbons, an aromatic ring fused by a non-aromatic ring, Formula III, and Formula IV,
- wherein each of X17 to X35 is independently C or N, and
- each Y2, Y3, and Y4 is independently selected from the group consisting of O, S, Se, NRY2, BRY2, BRY2RY3, CRY2RY3, SiRY2RY3, GeRY2RY3, C═O, C═S, C═NRY2, C═CRY2RY3, SO, SO2, or P(O)RY2 with the proviso that, if two of RA, two of RB, two of RC, or two of RD are joined to form an 5 or 6-membered cycloalkyl ring, then at least one of RA, RB, RC, or RD comprises a structure selected from the group consisting of deuterium, alkyldiarylsilyl, dialkylarylsilyl, trirylsilane, substituted triphenylsilyl, germyl, tetraphenylene, benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, a bridged polycyclic ring, an alkyl or cycloalkyl comprising five or more carbons, an aromatic ring fused by a non-aromatic ring, and Formula V:
- wherein each of X36 to X43 is independently C or N, and
- wherein Y5 is selected from the group consisting of O, S, Se, NRY4, BRY4, BRY4RY5, CRY4RY5, SiR4RY5, GeRY4RY5, C═O, C═S, C═NRY4, C═CRY4RY5, SO, SO2, or P(O)RY4;
- wherein each of RY1, RY2, RY3, RY4, RY5, RA, RB, RC, RD, and RE is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, 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, selenyl, and combinations thereof;
- wherein the compound is not:
15 more elements
An organic light emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an emissive region disposed between the anode and the cathode,
- wherein the emissive region comprises a compound comprising a structure of Formula I:
- wherein each of X1 to X16 is independently C or N;
- each of RA, RB, RC, and RD independently represents mono to the maximum allowable substitutions, or no substitutions;
- wherein any two of RA, RB, RC, and RD may be joined or fused to form a ring;
- with the proviso that, if the compound comprises a structure of Formula II:
- wherein each of X44 to X4 is independently C or N;
- wherein Y1 is selected from the group consisting of O, NRY1, and CMe2;
- wherein RE represents mono to the maximum allowable substitutions, or no substitutions;
- then
- (i) when Y1 is O or CMe2, then X5 is C, and
- (ii) when Y1 is NRY1, then RY1 and RE do not join to form a 5-membered ring;
- with the proviso that, if no two of RA, two of RB, two of RC, or two of RD are joined to form a ring, then at least one of RA, RB, RC, or RD comprises a structure selected from the group consisting of deuterium, alkyldiarylsilyl, dialkylarylsilyl, germyl, tetraphenylene, an alkyl or cycloalkyl comprising five or more carbons, and an aromatic ring fused by a non-aromatic ring;
- with the proviso that, if two of RA, two of RB, two of RC, or two of RD are joined to form a benzene ring, then at least one of RA, RB, RC, or RD comprises a structure selected from the group consisting of deuterium, silyl, germyl, tetraphenylene, benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (bimbim), an alkyl or cycloalkyl comprising five or more carbons, an aromatic ring fused by a non-aromatic ring, Formula III, and Formula IV,
- wherein each of X17 to X35 is independently C or N, and
- each Y2, Y3, and Y4 is independently selected from the group consisting of O, S, Se, NRY2, BRY2, BRY2RY3, CRY2RY3, SiRY2RY3, GeRY2RY3, C═O, C═S, C═NRY2, C═CRY2RY3, SO, SO2, or P(O)RY2 with the proviso that, if two of RA, two of RB, two of RC, or two of RD are joined to form an 5 or 6-membered cycloalkyl ring, then at least one of RA, RB, RC, or RD comprises a structure selected from the group consisting of deuterium, alkyldiarylsilyl, dialkylarylsilyl, triarylsilane, substituted triphenylsilyl, germyl, tetraphenylene, benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, an alkyl or cycloalkyl comprising five or more carbons, an aromatic ring fused by a non-aromatic ring, and Formula V:
- wherein each of X36 to X43 is independently C or N, and
- wherein Y5 is selected from the group consisting of O, S, Se, NRY4, BRY4, BRY4RY5, CRY4RY5, SiRY4RY5, GeRY4RY5, C═O, C═S, C═NRY4, C═CRY4RY5, SO, SO2, or P(O)RY4;
- wherein each of RY1, RY2, RY3, RY4, RY5, RA, RB, RC, RD, and RE is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, 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, selenyl, and combinations thereof;
- wherein the compound is not:
20 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 each of X1 to X16 is independently C or N;
- each of RA, RB, RC, and RD independently represents mono to the maximum allowable substitutions, or no substitutions;
- wherein any two of RA, RB, RC, and RD may be joined or fused to form a ring;
- with the proviso that, if the compound comprises a structure of Formula II:
- wherein each of X44 to X4 is independently C or N;
- wherein Y1 is selected from the group consisting of O, NRY1, and CMe2;
- wherein RE represents mono to the maximum allowable substitutions, or no substitutions;
- then
- (i) when Y1 is O or CMe2, then X15 is C, and
- (ii) when Y1 is NRY1, then RY1 and RE do not join to form a 5-membered ring;
- with the proviso that, if no two of RA, two of RB, two of RC, or two of RD are joined to form a ring, then at least one of RA, RB, RC, or RD comprises a structure selected from the group consisting of deuterium, alkyldiarylsilyl, dialkylarylsilyl, germyl, tetraphenylene, an alkyl or cycloalkyl comprising five or more carbons, and an aromatic ring fused by a non-aromatic ring;
- with the proviso that, if two of RA, two of RB, two of RC, or two of RD are joined to form a benzene ring, then at least one of RA, RB, RC, or RD comprises a structure selected from the group consisting of deuterium, silyl, germyl, tetraphenylene, benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (bimbim), an alkyl or cycloalkyl comprising five or more carbons, an aromatic ring fused by a non-aromatic ring, Formula III, and Formula IV,
- wherein each of X17 to X35 is independently C or N, and
- each Y2, Y3, and Y4 is independently selected from the group consisting of O, S, Se, NRY2, BRY2, BRY2RY3, CRY2RY3, SiRY2RY3, GeRY2RY3, C═O, C═S, C═NRY2, C═CRY2RY3, SO, SO2, or P(O)RY2;
- with the proviso that, if two of RA, two of RB, two of RC, or two of RD are joined to form an 5 or 6-membered cycloalkyl ring, then at least one of RA, RB, RC, or RD comprises a structure selected from the group consisting of deuterium, alkyldiarylsilyl, dialkylarylsilyl, triarylsilane, substituted triphenylsilyl, germyl, tetraphenylene, benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, an alkyl or cycloalkyl comprising five or more carbons, an aromatic ring fused by a non-aromatic ring, and Formula V:
- wherein each of X36 to X43 is independently C or N, and
- wherein Y5 is selected from the group consisting of O, S, Se, NRY4, BRY4, BRY4RY5, CRY4RY5, SiRY4RY5, GeRY4RY5, C═O, C═S, C═NRY4, C═CRY4RY5, SO, SO2, or P(O)RY4;
- wherein each of RY1, RY2, RY3, RY4, RY5, RA, RB, RC, RD, and RE is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, 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, selenyl, and combinations thereof;
- wherein the compound is not:
17 more elements
Dependencies are inferred from the claim text.