Heteroleptic iridium complexes as dopants

Novel phosphorescent heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands are provided. Alkyl substitution at specific positions on the ligands gives rise to compounds with improved OLED properties, including saturated green emission.

ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

Methods of making novel organic compounds containing a twisted aryl group are provided. In particular, the compounds provided contain a 2-phenylpyridine ligand having a twisted aryl group on the pyridine portion of the ligand. The compounds may be used in organic light emitting devices, particularly as emitting dopants. Devices comprising the compounds containing twisted aryl may demonstrate improved color, efficiency, stability and manufacturing. 2. The method of claim 1 , wherein the low boiling alcohol is selected from the group consisting of methanol claim 1 , ethanol claim 1 , n-propanol claim 1 , isopropanol claim 1 , n-butanol claim 1 , 1:1 ratio of ethanol and methanol claim 1 , 2-methoxyethanol claim 1 , and 2-ethoxyethanol.4. The method of claim 1 , wherein X is triflate.8. The method of claim 6 , wherein X is triflate. This application is a divisional application of co-pending U.S. patent application Ser. No. 14/791,741, filed Jul. 6, 2015, which is a continuation application of U.S. patent application Ser. No. 13/968,551, filed Aug. 16, 2013, now U.S. Pat. No. 9,076,973 issued on Jul. 7, 2015, which is a continuation application of U.S. patent application Ser. No. 13/062,141, filed May 20, 2011, now U.S. Pat. No. 8,519,384 issued on Aug. 27, 2013, which is a U.S. national phase application filed under 35 U.S.C. §371 of International Application No. PCT/US2009/55890, filed Sep. 3, 2009, which is a continuation-in-part of application No. PCT/US2009/052045, filed on Jul. 29, 2009, and claims priority to provisional application No. 61/093,967, filed on Sep. 3, 2008, provisional application No. 61/140,459, filed on Dec. 23, 2008, and provisional application No. 61/229,088, filed on Jul. 28, 2009.The present invention relates to organic materials that may be advantageously used in organic light emitting devices. More particularly, the present invention relates to a method of making organic materials for such devices, as well as novel organic materials.Opto- ...

Organic electroluminescent materials and devices

Novel phosphorescent platinum complexes containing tetradentate ligands are provided. The disclosed compounds have three 6-membered metallocycle units in each tertadentate ligand. The disclosed compounds have desirable electronic properties that make them useful when incorporated into a variety of OLED devices.

6-SUBSTITUTED 2-(BENZIMIDAZOLYL)PURINE AND PURINONE DERIVATIVES FOR IMMUNOSUPPRESSION

The present invention provides novel purinones and purines useful for the prevention and treatment of autoimmune diseases, inflammatory disease, mast cell mediated disease and transplant rejection. The compounds are of the general formulae I and II: ...

Phosphorescent materials

Compounds comprising a 2-phenylpyridine ligand further substituted with a heterocyclic group are provided. In particular, the compound comprises a 2-phenylpyridine ligand further substituted with a nitrogen-containing heterocycle. The compounds may be used in organic light emitting devices to provide devices having improved efficiency and lifetime.

Organic electroluminescent material and devices

Novel organic compounds containing a twisted aryl group are provided. In particular, the compounds provided contain a 2-phenylpyridine ligand having a twisted aryl group on the pyridine portion of the ligand. The compounds may be used in organic light emitting devices, particularly as emitting dopants. Devices comprising the compounds containing twisted aryl may demonstrate improved color, efficiency, stability and manufacturing. Additionally, methods are provided for making homoleptic Ir (III) compounds which may contain a twisted aryl.

1-(4-UREIDOBENZOYL)PIPERAZINE DERIVATIVES

The present invention relates to 1-(4-ureidobenzoyl)piperazine derivatives having the general Formula I (We bring to your attention that formula I is not provided on this electronic version as it is provided in the abstract of the paper copy) Wherein Ris (C)alkyl, (C)cycloalkyl or (C)cycloalkyl(C)alkyl, each of which may be substituted by hydroxy, cyano or halogen; Rrepresents 1 or 2 optional halogens; Ris (C)alkyl, (C)cycloalkyl or (C)cycloalkyl(C)alkyl, each of which may be substituted by one or more halogens; A represents a heteroaryl ring system comprising 1-3 heteroatoms selected from N, O and S, which ring system is 5- or 6-membered when X is C, and 5-membered when X is N; n is 1 or 2; or a pharmaceutically acceptable salt thereof; to pharmaceutical compositions comprising the same, and to the use of a these 1-(4-ureidobenzoyl)piperazine derivatives for the manufacture of a medicament for treating or preventing atherosclerosis and related disorders associated with cholesterol and bile acids transport and metabolism. 18-. (canceled)101. The 1-(4-ureidobenzoyl)piperazine derivative of claim , wherein A represents furan-2 ,5 ,diyl or pyridine-2 ,6-diyl.111. The 1-(4-ureidobenzoyl)piperazine derivative of claim , wherein Rrepresents 1 or 2 halogens selected from F and Cl.121. The 1-(4-ureidobenzoyl)piperazine derivative of claim , wherein Ris tert-butyl.131. The 1-(4-ureidobenzoyl)piperazine derivative of claim which is selected from:N-tert-butyl-5-((4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazin-1-yl)methyl)furan-2-carboxamide;N-tert-butyl-5-((4-(3-fluoro-4-(3-isobutylureido)benzoyl)piperazin-1-yl)methyl)furan-2-carboxamide;N-tert-butyl-5-((4-(4-(3-(cyclopropylmethyl)ureido)-3-fluorobenzoyl)piperazin-1-yl)methyl)furan-2-carboxamide;N-tert-butyl-5-((4-(3-fluoro-4-(3-neopentylureido)benzoyl)piperazin-1-yl)methyl)furan-2-carboxamide;N-tert-butyl-5-((4-(3-fluoro-4-(3-isopentylureido)benzoyl)piperazin-1-yl)methyl)furan-2-carboxamide;N-tert-butyl-5-((4-(4-(3- ...

PHOSPHORESCENT HETEROLEPTIC PHENYLBENZIMIDAZOLE DOPANTS

Novel phosphorescent heteroleptic iridium complexes with benzimidazole and phenylpyridine ligands are provided. These iridium complexes can improve OLED properties, and are useful in white light applications. 2. The compound of claim 1 , wherein n=2.3. The compound of claim 1 , wherein n=1.4. The compound of claim 1 , wherein Ris aryl or substituted aryl.5. The compound of claim 4 , wherein Ris a 2 claim 4 ,6-disubstituted aryl.7. The compound of claim 1 , wherein Ris alkyl.8. The compound of claim 1 , wherein R claim 1 , R claim 1 , Rand Rare each independently selected from the group consisting of hydrogen and alkyl claim 1 , and wherein at least one of R claim 1 , R claim 1 , Rand Ris alkyl.9. The compound of claim 1 , wherein Ris aryl.10. The compound of claim 1 , wherein Ris aryl.11. The compound of claim 1 , wherein R claim 1 , R claim 1 , and Rare hydrogen.14. The first device of claim 13 , wherein the organic layer is an emissive layer and the compound is an emissive dopant.15. The first device of claim 13 , wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.16. The first device of claim 13 , wherein the organic layer further comprises a host.17. The first device of claim 16 , wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;{'sub': n', '2n+1', 'n', '2n+1', '1', 'n', '2n+1', '2', '1', '2', 'n', '2n+1', 'n', '2n+1', '1', '1', '2', 'n', '2n', '1, 'wherein any substituent in the host is an unfused substituent independently selected from the group consisting of CH, OCH, OAr, N(CH), N(Ar)(Ar), CH═CH—CH, C≡CHCH, Ar, Ar—Ar, CH—Ar, or no substitution;'}wherein n is from 1 to 10; and{'sub': 1', '2, 'wherein Arand Arare independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.'}19. The first device of claim 16 , wherein the host is a metal complex.20. The first device of wherein the first device is ...

PHOSPHORESCENT HETEROLEPTIC PHENYLBENZIMIDAZOLE DOPANTS AND NEW SYNTHETIC METHODOLOGY

Novel heteroleptic iridium complexes are provided. These iridium complexes are useful compounds in OLED devices. The ligands for these novel complexes may be obtained using a new synthetic methodology that utilizes manganese dioxide. 3. The compound of claim 1 , wherein n=2.4. The compound of claim 1 , wherein n=1.5. The compound of claim 1 , wherein X is selected from the group consisting of O and S.6. The compound of claim 1 , wherein X is O.7. The compound of claim 1 , wherein X is S.8. The compound of claim 1 , wherein Ris aryl or substituted aryl.9. The compound of claim 1 , wherein Ris alkyl.10. The compound of claim 1 , wherein R claim 1 , R claim 1 , and Rare independently selected from the group consisting of hydrogen and alkyl claim 1 , and wherein at least one of R claim 1 , R claim 1 , and Ris alkyl.11. The compound of claim 1 , wherein Ris aryl or heteroaryl.12. The compound of claim 11 , wherein Ris phenyl or substituted phenyl.13. The compound of claim 8 , wherein Ris a 2 claim 8 ,6-disubstituted aryl.15. The compound of claim 2 , wherein R claim 2 , R claim 2 , and Rare hydrogen.19. The first device of claim 18 , wherein the organic layer is an emissive layer and the compound is an emissive dopant.20. The first device of claim 18 , wherein the organic layer further comprises a host.21. The first device of claim 20 , wherein the host comprises triphenylene containing benzo-fused thiophene or benzo-fused furan;{'sub': n', '2n+1', 'n', '2n+1', '1', 'n', '2n+1', '2', '1', '2', 'n', '2n+1', 'n', '2n+1', '1', '1', '2', 'n', '2n', '1, 'wherein any substituent in the host is an unfused substituent independently selected from the group consisting of CH, OCH, OAr, N(CH), N(Ar)(Ar), CH═CH—CH, C≡CHCH, Ar, Ar—Ar, CH—Ar, or no substitution;'}wherein n is from 1 to 10; and{'sub': 1', '2, 'wherein Arand Arare independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.'}23. The first ...

HETEROLEPTIC IRIDIUM COMPLEXES AS DOPANTS

Novel phosphorescent heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands are provided. Alkyl substitution at specific positions on the ligands gives rise to compounds with improved OLED properties, including saturated green emission. 2. The compound of claim 1 , wherein n is 2.3. The compound of claim 1 , wherein X is O.4. The compound of claim 1 , wherein Ris hydrogen and Ris alkyl.5. The compound of claim 1 , wherein Ris alkyl and Ris hydrogen.6. The compound of claim 1 , wherein Rand Rare alkyl.7. The compound of claim 1 , wherein Ror Rare independently selected from the group consisting of branched alkyl claim 1 , cyclic alkyl claim 1 , bicyclic alkyl claim 1 , and multicyclic alkyl.8. The compound of claim 1 , wherein Ror Ris iso-propyl.9. The compound of claim 1 , wherein Ror Rcontain one or more deuterium atoms.10. The compound of claim 1 , wherein Rand Rcontain one or more deuterium atoms.11. The compound of claim 1 , wherein R claim 1 , R claim 1 , Rand Rare independently selected from the group consisting of hydrogen claim 1 , deuterium claim 1 , alkyl claim 1 , aryl claim 1 , and combinations thereof.12. The compound of claim 1 , wherein at least one of R claim 1 , R claim 1 , Rand Rcomprises a branched alkyl claim 1 , cyclic alkyl claim 1 , bicyclic alkyl claim 1 , or a multicyclic alkyl.13. The compound of claim 1 , wherein R claim 1 , R claim 1 , Ror Rcontain one or more deuterium atoms.16. The first device of claim 15 , wherein the first device is a consumer product.17. The first device of claim 15 , wherein the first device is an organic light-emitting device.18. The first device of claim 15 , wherein the first device comprises a lighting panel.19. The first device of claim 15 , wherein the organic layer is an emissive layer and the compound is an emissive dopant.20. The first device of claim 15 , wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.21. The first device of claim 15 , ...

Cyclometallated tetradentate platinum complexes

Novel phosphorescent platinum complexes containing tetradentate ligands are provided. The disclosed compounds have three 6-membered metallocycle units in each tertadentate ligand. The disclosed compounds have desirable electronic properties that make them useful when incorporated into a variety of OLED devices.

Phosphorescent materials

Novel organic compounds containing a twisted aryl group are provided. In particular, the compounds provided contain a 2-phenylpyridine ligand having a twisted aryl group on the pyridine portion of the ligand. The compounds may be used in organic light emitting devices, particularly as emitting dopants. Devices comprising the compounds containing twisted aryl may demonstrate improved color, efficiency, stability and manufacturing. Additionally, methods are provided for making homoleptic Ir (III) compounds which may contain a twisted aryl.

ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

Organometallic compounds comprising an imidazole carbene ligand having a N-containing ring fused to the imidazole ring are provided. In particular, the N-containing ring fused to the imidazole ring may contain one nitrogen atom or more than one nitrogen atom. These compounds may demonstrate high photoluminescent (PL) efficiency, Gaussian emission spectra, and/or short excited state lifetimes. These materials may be especially useful as blue phosphorescent emitters. 2. The compound of claim 1 , wherein A is benzene.3. The compound of claim 1 , wherein the metal M is Ir or Pt.4. The compound of claim 1 , wherein the metal M is Ir.5. The compound of claim 1 , wherein Ris alkyl or cycloalkyl.6. The compound of claim 1 , wherein Ris aryl.7. The compound of claim 1 , wherein Ris an electron donating group with a Hammett sigma constant less than 0.8. The compound of claim 7 , wherein Ris selected from the group consisting of alkyl claim 7 , arylamino claim 7 , alkylamino claim 7 , aryloxyl claim 7 , and alkyloxyl.10. The compound of claim 1 , wherein the compound is homoleptic.11. The compound of claim 1 , wherein the compound is heteroleptic.13. The compound of claim 12 , wherein m is 3.14. The compound of claim 12 , wherein L′ is a monoanionic bidentate ligand.18. The first device of claim 17 , wherein the organic layer is an emissive layer and the compound comprising the ligand L is an emissive dopant.19. The first device of claim 18 , wherein the organic layer further comprises a host.21. The first device of claim 19 , wherein the host is a metal complex.22. The first device of claim 17 , wherein the first device is selected from the group consisting of an organic light emitting device and a consumer product. This application is a continuation of U.S. patent application Ser. No. 13/043,180, filed on Mar. 8, 2011, the entire contents of which is incorporated herein by reference.The claimed invention was made by, on behalf of, and/or in connection with one or more of the ...

ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

Organometallic compounds comprising an imidazole carbene ligand having a N-containing ring fused to the imidazole ring are provided. In particular, the N-containing ring fused to the imidazole ring may contain one nitrogen atom or more than one nitrogen atom. These compounds may demonstrate high photoluminescent (PL) efficiency, Gaussian emission spectra, and/or short excited state lifetimes. These materials may be especially useful as blue phosphorescent emitters. 2. The compound of claim 1 , wherein A is benzene.3. The compound of claim 1 , wherein Ris alkyl or cycloalkyl.4. The compound of claim 1 , wherein Ris aryl.5. The compound of claim 1 , wherein Ris an electron donating group with a Hammett sigma constant less than 0.6. The compound of claim 5 , wherein Ris selected from the group consisting of alkyl claim 5 , arylamino claim 5 , alkylamino claim 5 , aryloxyl claim 5 , and alkyloxyl.10. The first device of claim 9 , wherein the organic layer is an emissive layer and the compound comprising the ligand L is an emissive dopant.11. The first device of claim 9 , wherein the organic layer further comprises a host.13. The first device of claim 11 , wherein the host is a metal complex.14. The first device of claim 11 , wherein the host is a metal carbene complex.15. The first device of claim 9 , wherein the first device is an organic light emitting device.17. The consumer product of claim 16 , wherein the consumer product is selected from the group consisting of flat panel displays claim 16 , computer monitors claim 16 , televisions claim 16 , billboards claim 16 , lights for interior or exterior illumination and/or signaling claim 16 , heads up displays claim 16 , fully transparent displays claim 16 , flexible displays claim 16 , laser printers claim 16 , telephones claim 16 , cell phones claim 16 , personal digital assistants (PDAs) claim 16 , laptop computers claim 16 , digital cameras claim 16 , camcorders claim 16 , viewfinders claim 16 , vehicles claim 16 , ...

ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

A compound of: 2. The compound of claim 1 , wherein only one of R claim 1 , R claim 1 , R claim 1 , and Ris not hydrogen.3. The compound of claim 1 , wherein only one of R claim 1 , R claim 1 , R claim 1 , and Ris alkyl.4. The compound of claim 1 , wherein only one of R claim 1 , R claim 1 , R claim 1 , and Rsubstituents is ethyl.5. The compound of claim 1 , wherein only one of R claim 1 , R claim 1 , R claim 1 , and Rsubstituents is methyl.6. The compound of claim 1 , wherein Rand Rare hydrogen and one of Rand Ris alkyl.7. The compound of claim 1 , wherein one of Rand Ris alkyl and Rand Rare hydrogen.8. The compound of claim 1 , wherein the metal M is Ir.10. The compound of claim 1 , wherein the compound is homoleptic.11. The compound of claim 1 , wherein the compound is heteroleptic.13. The compound of claim 9 , wherein the metal M is Ir.15. The device of claim 14 , wherein the metal M is Ir.17. The device of claim 16 , wherein the metal M is Ir.18. The device of claim 14 , wherein the organic layer is an emissive layer and the compound having a structure of Formula IV is an emitting dopant.20. The consumer product of claim 19 , wherein the consumer product is one of a flat panel display claim 19 , a computer monitor claim 19 , a television claim 19 , a billboard claim 19 , a light for interior or exterior illumination and/or signaling claim 19 , a heads up display claim 19 , a fully transparent display claim 19 , a flexible display claim 19 , a laser printer claim 19 , a telephone claim 19 , a cell phone claim 19 , a personal digital assistant (PDA) claim 19 , a laptop computer claim 19 , a digital camera claim 19 , a camcorder claim 19 , a viewfinder claim 19 , a micro-display claim 19 , a vehicle claim 19 , a large area wall claim 19 , theater or stadium screen claim 19 , or a sign. This application is a continuation of co-pending U.S. patent application Ser. No. 16/742,028, filed Jan. 14, 2020, which is a continuation of co-pending U.S. patent application Ser. ...

HETEROLEPTIC IRIDIUM COMPLEXES AS DOPANTS

Novel phosphorescent heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands are provided. Alkyl substitution at specific positions on the ligands gives rise to compounds with improved OLED properties, including saturated green emission. 2. The compound of claim 1 , wherein n is 2.3. The compound of claim 1 , wherein X is O.4. The compound of claim 1 , wherein Ris hydrogen and Ris alkyl.5. The compound of claim 1 , wherein Ris alkyl and Ris hydrogen.6. The compound of claim 1 , wherein Rand Rare alkyl.7. The compound of claim 1 , wherein Ror Rare independently selected from the group consisting of branched alkyl claim 1 , cyclic alkyl claim 1 , bicyclic alkyl claim 1 , and multicyclic alkyl.8. The compound of claim 1 , wherein Ror Ris iso-propyl.9. The compound of claim 1 , wherein Ror Rcontain one or more deuterium atoms.10. The compound of claim 1 , wherein Rand Rcontain one or more deuterium atoms.11. The compound of claim 1 , wherein R claim 1 , R claim 1 , Rand Rare independently selected from the group consisting of hydrogen claim 1 , deuterium claim 1 , alkyl claim 1 , aryl claim 1 , and combinations thereof.12. The compound of claim 1 , wherein at least one of R claim 1 , R claim 1 , Rand Rcomprises a branched alkyl claim 1 , cyclic alkyl claim 1 , bicyclic alkyl claim 1 , or a multicyclic alkyl.13. The compound of claim 1 , wherein R claim 1 , R claim 1 , Ror Rcontain one or more deuterium atoms.16. The first device of claim 15 , wherein the first device is a consumer product.17. The first device of claim 15 , wherein the first device is an organic light-emitting device.18. The first device of claim 15 , wherein the first device comprises a lighting panel.19. The first device of claim 15 , wherein the organic layer is an emissive layer and the compound is an emissive dopant.20. The first device of claim 15 , wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.21. The first device of claim 15 , ...

HETEROLEPTIC IRIDIUM COMPLEXES AS DOPANTS

Novel phosphorescent heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands are provided. Alkyl substitution at specific positions on the ligands gives rise to compounds with improved OLED properties, including saturated green emission. 2. The compound of claim 1 , wherein n is 2.3. The compound of claim 1 , wherein X is O.4. The compound of claim 1 , wherein Ris hydrogen and Ris alkyl.6. The compound of claim 1 , wherein Rand Rare alkyl.7. The compound of claim 1 , wherein Ror Rare independently selected from the group consisting of branched alkyl claim 1 , cyclic alkyl claim 1 , bicyclic alkyl claim 1 , and multicyclic alkyl.8. The compound of claim 1 , wherein Ror Ris iso-propyl.9. The compound of claim 1 , wherein Ror Rcontain one or more deuterium atoms.10. The compound of claim 1 , wherein Rand Rcontain one or more deuterium atoms.11. The compound of claim 1 , wherein R claim 1 , R claim 1 , Rand Rare independently selected from the group consisting of hydrogen claim 1 , deuterium claim 1 , alkyl claim 1 , aryl claim 1 , and combinations thereof.12. The compound of claim 1 , wherein at least one of R claim 1 , R claim 1 , Rand Rcomprises a branched alkyl claim 1 , cyclic alkyl claim 1 , bicyclic alkyl claim 1 , or a multicyclic alkyl.13. The compound of claim 1 , wherein R claim 1 , R claim 1 , Ror Rcontain one or more deuterium atoms.16. The first device of claim 15 , wherein the first device is selected from the group consisting of a consumer product claim 15 , an organic light-emitting device claim 15 , a lighting panel claim 15 , and a combination thereof.17. The first device of claim 15 , wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.18. The first device of claim 15 , wherein organic layer comprises a host claim 15 , and the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;{'sub': n', '2n+1', 'n', '2n+1', '1', 'n', '2n+1', '2', '1', '2', 'n', '2n+1', ' ...

ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

Organometallic compounds comprising an imidazole carbene ligand having a N-containing ring fused to the imidazole ring are provided. In particular, the N-containing ring fused to the imidazole ring may contain one nitrogen atom or more than one nitrogen atom. These compounds may demonstrate high photoluminescent (PL) efficiency, Gaussian emission spectra, and/or short excited state lifetimes. These materials may be especially useful as blue phosphorescent emitters. 2. The compound of claim 1 , wherein A is benzene.3. The compound of claim 1 , wherein the metal M is Ir or Pt.4. The compound of claim 1 , wherein Ris alkyl or cycloalkyl.5. The compound of claim 1 , wherein Ris aryl.6. The compound of claim 1 , wherein Ris an electron donating group with a Hammett sigma constant less than 0.7. The compound of claim 6 , wherein Ris selected from the group consisting of alkyl claim 6 , arylamino claim 6 , alkylamino claim 6 , aryloxyl claim 6 , and alkyloxyl.9. The compound of claim 1 , wherein the compound is homoleptic.10. The compound of claim 1 , wherein the compound is heteroleptic.12. The compound of claim 11 , wherein m is 3.13. The compound of claim 11 , wherein L′ is a monoanionic bidentate ligand.17. The first device of claim 16 , wherein the organic layer is an emissive layer and the compound comprising the ligand L is an emissive dopant.19. The first device of claim 16 , wherein the first device is selected from the group consisting of an organic light emitting device and a consumer product. This application is a divisional of U.S. patent application Ser. No. 14/511,689, filed on Oct. 10, 2014, which is a continuation of U.S. patent application Ser. No. 13/043,180, filed on Mar. 8, 2011, the entire contents of which are incorporated herein by reference.The claimed invention was made by, on behalf of, and/or in connection with one or more of the following parties to a joint university corporation research agreement: Regents of the University of Michigan, ...

Organic electroluminescent materials and devices

Methods of making novel organic compounds containing a twisted aryl group are provided. In particular, the compounds provided contain a 2-phenylpyridine ligand having a twisted aryl group on the pyridine portion of the ligand. The compounds may be used in organic light emitting devices, particularly as emitting dopants. Devices comprising the compounds containing twisted aryl may demonstrate improved color, efficiency, stability and manufacturing.

Heteroleptic iridium complexes as dopants

Novel phosphorescent heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands are provided. Alkyl substitution at specific positions on the ligands gives rise to compounds with improved OLED properties, including saturated green emission.

ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

An OLED containing an emissive dopant that is a heteroleptic complex having the formula Ir(L)(L) is disclosed. In the formula, Lis 2. The OLED of claim 1 , wherein R claim 1 , R claim 1 , R claim 1 , Rand Rare each independently selected from hydrogen and methyl.6. The OLED of claim 5 , wherein R claim 5 , R claim 5 , R claim 5 , Rand Rare each independently selected from hydrogen and methyl.10. The consumer product of claim 9 , wherein R claim 9 , R claim 9 , R claim 9 , Rand Rare each independently selected from hydrogen and methyl. This application is a continuation of co-pending U.S. patent application Ser. No. 16/201,354, filed Nov. 27, 2018, which is a continuation of U.S. patent application Ser. No. 15/467,724, filed Mar. 23, 2017, now U.S. Pat. No. 10,186,672 issued on Jan. 22, 2019, which is a divisional application of U.S. patent application Ser. No. 14/791,741, filed Jul. 6, 2015, now U.S. Pat. No. 9,630,983 issued on Apr. 25, 2017, which is a continuation application of U.S. patent application Ser. No. 13/968,551, filed Aug. 16, 2013, now U.S. Pat. No. 9,076,973 issued on Jul. 7, 2015, which is a continuation application of U.S. patent application Ser. No. 13/062,141, filed May 20, 2011, now U.S. Pat. No. 8,519,384 issued on Aug. 27, 2013, which is a U.S. national phase application filed under 35 U.S.C. § 371 of International Application No. PCT/US2009/55890, filed Sep. 3, 2009, which is a continuation-in-part of application No. PCT/US2009/052045, filed on Jul. 29, 2009, and claims priority to provisional application No. 61/093,967, filed on Sep. 3, 2008, provisional application No. 61/140,459, filed on Dec. 23, 2008, and provisional application No. 61/229,088, filed on Jul. 28, 2009.The present invention relates to organic materials that may be advantageously used in organic light emitting devices. More particularly, the present invention relates to a method of making organic materials for such devices, as well as novel organic materials.Opto-electronic ...

METHOD OF MAKING ORGANIC ELECTROLUMINESCENT MATERIALS

A method of making ligands for producing novel heteroleptic iridium complexes is provided. The method includes reacting the condensation product of an aryl 1,2-diamine and an aryl aldehyde with manganese dioxide in a solvent. The novel iridium complexes produced using the ligands are useful compounds in OLED devices. 3. The method of claim 2 , wherein the phase transfer catalyst comprises 1-hexadecylpyridinium bromide.4. The method of claim 1 , wherein Ris aryl or substituted aryl.5. The method of claim 1 , wherein Ris a 2 claim 1 ,6-disubstituted aryl.6. The method of claim 1 , wherein Ris alkyl. This application is a divisional of U.S. patent application Ser. No. 13/111,555, filed May 19, 2011, the entire content of which is incorporated herein by reference.The claimed invention was made by, on behalf of, and/or in connection with one or more of the following parties to a joint university corporation research agreement: Regents of the University of Michigan, Princeton University, The University of Southern California, and the Universal Display Corporation. The agreement was in effect on and before the date the claimed invention was made, and the claimed invention was made as a result of activities undertaken within the scope of the agreement.The present invention relates to compounds useful for incorporation into OLEDs, specifically heteroleptic iridium complexes, and methods of making phenylbenzimidazole ligands.Opto-electronic devices that make use of organic materials are becoming increasingly desirable for a number of reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications such as fabrication on a flexible substrate. Examples of organic opto-electronic devices include organic light emitting devices ...

HETEROLEPTIC IRIDIUM COMPLEXES AS DOPANTS

Novel phosphorescent heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands are provided. Alkyl substitution at specific positions on the ligands gives rise to compounds with improved OLED properties, including saturated green emission. 2. The compound of claim 1 , wherein n is 2.3. The compound of claim 1 , wherein X is O.4. The compound of claim 1 , wherein Ris hydrogen and Ris alkyl.5. The compound of claim 1 , wherein Ris alkyl and Ris hydrogen.6. The compound of claim 1 , wherein Rand Rare alkyl.7. The compound of claim 1 , wherein Ror Rare independently selected from the group consisting of branched alkyl claim 1 , cyclic alkyl claim 1 , bicyclic alkyl claim 1 , and multicyclic alkyl.8. The compound of claim 1 , wherein Ror Ris iso-propyl.9. The compound of claim 1 , wherein Ror Rcontain one or more deuterium atoms.10. The compound of claim 1 , wherein Rand Rcontain one or more deuterium atoms.11. The compound of claim 1 , wherein R claim 1 , R claim 1 , Rand Rare independently selected from the group consisting of hydrogen claim 1 , deuterium claim 1 , alkyl claim 1 , aryl claim 1 , and combinations thereof.12. The compound of claim 1 , wherein at least one of R claim 1 , R claim 1 , Rand Rcomprises a branched alkyl claim 1 , cyclic alkyl claim 1 , bicyclic alkyl claim 1 , or a multicyclic alkyl.13. The compound of claim 1 , wherein R claim 1 , R claim 1 , Ror Rcontain one or more deuterium atoms.16. The first device of claim 15 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.17. The first device of claim 15 , wherein the organic layer further comprises a host.18. The first device of claim 17 , wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;{'sub': n', '2n+1', 'n', '2n+1', '1', 'n', '2n+1', '2', '1', '2', 'n', '2n+1', 'n', '2n+1', '1', '1', '2', 'n', '2n', '1, 'wherein any substituent in the host is an unfused ...

PHOSPHORESCENT MATERIALS

Novel organic compounds containing a twisted aryl group are provided. In particular, the compounds provided contain a 2-phenylpyridine ligand having a twisted aryl group on the pyridine portion of the ligand. The compounds may be used in organic light emitting devices, particularly as emitting dopants. Devices comprising the compounds containing twisted aryl may demonstrate improved color, efficiency, stability and manufacturing. Additionally, methods are provided for making homoleptic Ir (III) compounds which may contain a twisted aryl. 2. The method of claim 1 , wherein the low boiling alcohol is selected from the group consisting of methanol claim 1 , ethanol claim 1 , n-propanol claim 1 , isopropanol claim 1 , n-butanol claim 1 , 1:1 ratio of ethanol and methanol claim 1 , 2-methoxyethanol claim 1 , and 2-ethoxyethanol.4. The method of claim 1 , wherein X is triflate.8. The method of claim 6 , wherein X is triflate.11. The method of claim 10 , wherein X is selected from the group consisting of triflate claim 10 , tosylate claim 10 , trifluoroacetate claim 10 , tetrafluoroborate claim 10 , and hexafluorophosphate.12. The method of claim 10 , wherein R claim 10 , R claim 10 , R claim 10 , and Rare selected from the group consisting of benzene claim 10 , pyrimidine claim 10 , pyridine claim 10 , thiophene claim 10 , thianaphthene claim 10 , fluorine claim 10 , carbazole claim 10 , and dibenzothiophene. This application is a continuation application of the co-pending U.S. patent application Ser. No. 13/968,551, filed Aug. 16, 2013, which is a continuation application of U.S. patent application Ser. No. 13/062,141, filed May 20, 2011, now U.S. Pat. No. 8,519,384 issued on Aug. 27, 2013, which is a U.S. national phase application filed under 35 U.S.C. §371 of International Application No. PCT/US2009/55890, filed Sep. 3, 2009, which is a continuation-in-part of application No. PCT/US2009/052045, filed on Jul. 29, 2009, claiming priority to provisional application No. ...

Phosphorescent materials

Novel organic compounds containing a twisted aryl group are provided. In particular, the compounds provided contain a 2-phenylpyridine ligand having a twisted aryl group on the pyridine portion of the ligand. The compounds may be used in organic light emitting devices, particularly as emitting dopants. Devices comprising the compounds containing twisted aryl may demonstrate improved color, efficiency, stability and manufacturing. Additionally, methods are provided for making homoleptic Ir (III) compounds which may contain a twisted aryl.

Heteroleptic iridium complexes as dopants

Novel phosphorescent heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands are provided. Alkyl substitution at specific positions on the ligands gives rise to compounds with improved OLED properties, including saturated green emission.

Phosphorescent heteroleptic phenylbenzimidazole dopants and new synthetic methodology

Novel heteroleptic iridium complexes are provided. These iridium complexes are useful compounds in OLED devices. The ligands for these novel complexes may be obtained using a new synthetic methodology that utilizes manganese dioxide.

Pyridyl carbene phosphorescent emitters

Organometallic compounds comprising an imidazole carbene ligand having a N-containing ring fused to the imidazole ring are provided. In particular, the N-containing ring fused to the imidazole ring may contain one nitrogen atom or more than one nitrogen atom. These compounds may demonstrate high photoluminescent (PL) efficiency, Gaussian emission spectra, and/or short excited state lifetimes. These materials may be especially useful as blue phosphorescent emitters.

Phosphorescent materials

Compounds comprising a 2-phenylpyridine ligand further substituted with a heterocyclic group are provided. In particular, the compound comprises a 2-phenylpyridine ligand further substituted with a nitrogen-containing heterocycle. The compounds may be used in organic light emitting devices to provide devices having improved efficiency and lifetime.

Phosphorescent heteroleptic phenylbenzimidazole dopants

Novel phosphorescent heteroleptic iridium complexes with benzimidazole and phenylpyridine ligands are provided. These iridium complexes can improve OLED properties, and are useful in white light applications.

Organic electroluminescent materials and devices

Novel heteroleptic iridium complexes are described. These iridium compounds contain alkyl substituted phenylpyridine ligands, which provide these compounds with beneficial properties when the iridium complexes are incorporated into OLED devices.

Phosphorescent materials

Novel organic compounds containing a twisted aryl group are provided. In particular, the compounds provided contain a 2-phenylpyridine ligand having a twisted aryl group on the pyridine portion of the ligand. The compounds may be used in organic light emitting devices, particularly as emitting dopants. Devices comprising the compounds containing twisted aryl may demonstrate improved color, efficiency, stability and manufacturing. Additionally, methods are provided for making homoleptic Ir (III) compounds which may contain a twisted aryl.

Organic electroluminescent materials and devices

A compound of: is disclosed. In Formula IV, ring B and ring C are each independently a 5 or 6-membered carbocyclic or heterocyclic ring; A-B represents a bonded pair of carbocyclic or heterocyclic rings coordinated to a metal M via a nitrogen atom in ring A and an sp 2 hybridized atom in ring B; A-C represents a bonded pair of carbocyclic or heterocyclic rings; M is a metal having an atomic number greater than 40; L′ is a monoanionic bidentate ligand; m is the oxidation state of the metal M; and n is at least 1.

Organic electroluminescent materials and devices

Methods of making novel organic compounds containing a twisted aryl group are provided. In particular, the compounds provided contain a 2-phenylpyridine ligand having a twisted aryl group on the pyridine portion of the ligand. The compounds may be used in organic light emitting devices, particularly as emitting dopants. Devices comprising the compounds containing twisted aryl may demonstrate improved color, efficiency, stability and manufacturing.

Organic electroluminescent materials and devices

An OLED containing an emissive dopant that is a heteroleptic complex having the formula Ir(L A-B ) 2 (L C-D ) is disclosed. In the formula, L A-B is and L C-D can be selected from

Organic electroluminescent materials and devices

Methods of making novel organic compounds containing a twisted aryl group are provided. In particular, the compounds provided contain a 2-phenylpyridine ligand having a twisted aryl group on the pyridine portion of the ligand. The compounds may be used in organic light emitting devices, particularly as emitting dopants. Devices comprising the compounds containing twisted aryl may demonstrate improved color, efficiency, stability and manufacturing.

Heteroleptic iridium complexes as dopants

Novel phosphorescent heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands are provided. Alkyl substitution at specific positions on the ligands gives rise to compounds with improved OLED properties, including saturated green emission.

Heteroleptic iridium complexes as dopants

Novel phosphorescent heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands are provided. Alkyl substitution at specific positions on the ligands gives rise to compounds with improved OLED properties, including saturated green emission.

Organic electroluminescent materials and devices

Novel phosphorescent heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands are provided. Alkyl substitution at specific positions on the ligands gives rise to compounds with improved OLED properties, including saturated green emission.

Organic electroluminescent materials and devices

Organometallic compounds comprising an imidazole carbene ligand having a N-containing ring fused to the imidazole ring are provided. In particular, the N-containing ring fused to the imidazole ring may contain one nitrogen atom or more than one nitrogen atom. These compounds may demonstrate high photoluminescent (PL) efficiency, Gaussian emission spectra, and/or short excited state lifetimes. These materials may be especially useful as blue phosphorescent emitters.

Organic electroluminescent materials and devices

Organometallic compounds comprising an imidazole carbene ligand having a N-containing ring fused to the imidazole ring are provided. In particular, the N-containing ring fused to the imidazole ring may contain one nitrogen atom or more than one nitrogen atom. These compounds may demonstrate high photoluminescent (PL) efficiency, Gaussian emission spectra, and/or short excited state lifetimes. These materials may be especially useful as blue phosphorescent emitters.

Method of making organic electroluminescent materials

A method of making ligands for producing novel heteroleptic iridium complexes is provided. The method includes reacting the condensation product of an aryl 1,2-diamine and an aryl aldehyde with manganese dioxide in a solvent. The novel iridium complexes produced using the ligands are useful compounds in OLED devices.

Phosphorescent materials

Novel organic compounds containing a twisted aryl group are provided. In particular, the compounds provided contain a 2-phenylpyridine ligand having a twisted aryl group on the pyridine portion of the ligand. The compounds may be used in organic light emitting devices, particularly as emitting dopants. Devices comprising the compounds containing twisted aryl may demonstrate improved color, efficiency, stability and manufacturing. Additionally, methods are provided for making homoleptic Ir (III) compounds which may contain a twisted aryl.

Phosphorescent materials

Compounds comprising a 2-phenylpyridine ligand further substituted with a heterocyclic group are provided. In particular, the compound comprises a 2-phenylpyridine ligand further substituted with a nitrogen-containing heterocycle. The compounds may be used in organic light emitting devices to provide devices having improved efficiency and lifetime.

Phosphorescent materials

Novel organic compounds containing a twisted aryl group are provided. In particular, the compounds provided contain a 2-phenylpyridine ligand having a twisted aryl group on the pyridine portion of the ligand. The compounds may be used in organic light emitting devices, particularly as emitting dopants. Devices comprising the compounds containing twisted aryl may demonstrate improved color, efficiency, stability and manufacturing. Additionally, methods are provided for making homoleptic Ir (III) compounds which may contain a twisted aryl.

High efficiency yellow light emitters for OLED devices

本發明闡述新穎的雜配位銥錯合物。該等銥化合物含有經烷基取代之苯基吡啶配位體，當將該等銥錯合物納入OLED裝置中時，其向該等化合物提供有益性質。

Heteroleptic iridium complexes as dopants

【課題】フェニルピリジン及びジベンゾ含有配位子をもつ新規な燐光ヘテロレプティックイリジウム錯体を提供する。【解決手段】フェニルピリジン及びジベンゾ含有配位子をもつ新規な燐光ヘテロレプティックイリジウム錯体を提供する。その配位子の特定の位置のアルキル置換は、向上したＯＬＥＤ特性をもつ化合物をもたらし、それには飽和緑色発光も含まれる。【選択図】図３

N-benzyl, n' -arylcarbonylpiperazine derivatives as lxr modulators

The present invention relates to N-benzyl,N'-arylcarbonylpiperazine derivatives having the general Formula (I) to pharmaceutical compositions comprising the same, and to the use of a these N-benzyl,N'-arylcarbonylpiperazine derivatives for the manufacture of a medicament for treating or preventing atherosclerosis and related disorders associated with cholesterol and bile acids transport and metabolism.

1-(4-ureidobenzoyl)piperazine derivatives

The present invention relates to 1-(4-ureidobenzoyl)piperazine derivatives having the general Formula I (We bring to your attention that formula I is not provided on this electronic version as it is provided in the abstract of the paper copy) Wherein R

Phosphorescent materials

【課題】有機発光性デバイスにおいて有利に使用できるヘテロレプティックイリジウム化合物を提供する。【解決手段】例えば下式で示される化合物が例示される。発光性ドーパントとして化合物1を含む発光層を有するデバイスは、デバイス安定性に有益である【選択図】図３

Organic electroluminescent materials and devices

Organometallic compounds comprising an imidazole carbene ligand having a N-containing ring fused to the imidazole ring are provided. In particular, the N-containing ring fused to the imidazole ring may contain one nitrogen atom or more than one nitrogen atom. These compounds may demonstrate high photoluminescent (PL) efficiency, Gaussian emission spectra, and/or short excited state lifetimes. These materials may be especially useful as blue phosphorescent emitters.

N-benzyl, n' -arylcarbonylpiperazine derivatives as lxr modulators

The present invention relates to N-benzyl,N' -arylcarbonylpiperazine derivatives having the general Formula (I) to pharmaceutical compositions comprising the same, and to the use of a these N-benzyl,N' -arylcarbonylpiperazine derivatives for the manufacture of a medicament for treating or preventing atherosclerosis and related disorders associated with cholesterol and bile acids transport and metabolism.

Phosphorescent materials

Compounds comprising a 2-phenylpyridine ligand further substituted with a heterocyclic group are provided. In particular, the compound comprises a 2-phenylpyridine ligand further substituted with a nitrogen-containing heterocycle. The compounds may be used in organic light emitting devices to provide devices having improved efficiency and lifetime.

Phosphorescent materials

Novel organic compounds containing a twisted aryl group are provided. In particular, the compounds provided contain a 2-phenylpyridine ligand having a twisted aryl group on the pyridine portion of the ligand. The compounds may be used in organic light emitting devices, particularly as emitting dopants. Devices comprising the compounds containing twisted aryl may demonstrate improved color, efficiency, stability and manufacturing. Additionally, methods are provided for making homoleptic Ir (III) compounds which may contain a twisted aryl.

ドーパントとしてのヘテロレプティックイリジウム錯体

【課題】フェニルピリジン及びジベンゾ含有配位子をもつ新規な燐光ヘテロレプティックイリジウム錯体を提供する。【解決手段】フェニルピリジン及びジベンゾ含有配位子をもつ新規な燐光ヘテロレプティックイリジウム錯体を提供する。その配位子の特定の位置のアルキル置換は、向上したＯＬＥＤ特性をもつ化合物をもたらし、それには飽和緑色発光も含まれる。【選択図】図３

Heteroleptic iridium complexes as dopants

Novel phosphorescent heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands are provided. Alkyl substitution at specific positions on the ligands gives rise to compounds with improved OLED properties, including saturated green emission.

Phosphorescent materials

Novel organic compounds containing a twisted aryl group are provided. In particular, the compounds provided contain a 2-phenylpyridine ligand having a twisted aryl group on the pyridine portion of the ligand. The compounds may be used in organic light emitting devices, particularly as emitting dopants. Devices comprising the compounds containing twisted aryl may demonstrate improved color, efficiency, stability and manufacturing. Additionally, methods are provided for making homoleptic Ir (III) compounds which may contain a twisted aryl.

5-phenyl-isoxazol-3-carboxamid-derivate als trpv1-modulatoren

N-benzyl-n'-arylcarbonylpiperazinderivate als lxr-modulatoren

Heteroleptic iridium complexes as dopants

Novel phosphorescent heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands are provided. Alkyl substitution at specific positions on the ligands gives rise to compounds with improved OLED properties, including saturated green emission.

6-substituted 2-(benzimidazolyl)purine and purinone derivatives and 6-substituted 2-(imidazoioý4,5- c¨pyridinyl)purine and purinone derivatives for immunosuppression