Source: https://patents.justia.com/patent/9577201
Timestamp: 2019-10-16 22:13:17
Document Index: 169521693

Matched Legal Cases: ['Application No. 201210371182', 'Application No. 201210371182', 'Application No. 201210371182', 'Application No. 2013', 'Application No. 2015', 'Application No. 104127056', 'Application No. 12159690']

US Patent for Organic electroluminescent materials and devices Patent (Patent # 9,577,201 issued February 21, 2017) - Justia Patents Search
Justia Patents Fluroescent, Phosphorescent, Or Luminescent LayerUS Patent for Organic electroluminescent materials and devices Patent (Patent # 9,577,201)
Aug 14, 2015 - UNIVERSAL DISPLAY CORPORATION
A compound including a ligand having the formula: is disclosed. In these formulas, each R1, R2, and R3 is independently selected from hydrogen, alkyl, and aryl; at least one of R1 and R2 is a branched alkyl containing at least 4 carbon atoms, where the branching occurs at a position further than the benzylic position; where R1 and R3 are mono-, di-, tri-, tetra-, or no substitutions; and R2 is mono-, di-, or no substitutions. Heteroleptic iridium complexes including such compounds, and devices including such compounds are also disclosed.
This application is a continuation application of U.S. patent application Ser. No. 13/849,028, filed Mar. 22, 2013, which is a continuation of U.S. patent application Ser. No. 12/044,234, now U.S. Pat. No. 8,431,243, filed Mar. 7, 2008, which claims priority to U.S. Provisional Application 60/905,758 filed Mar. 8, 2007, the entireties 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: The 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.
Due to strong spin-orbit coupling that leads to singlet-triplet state mixing, heavy metal complexes often display efficient phosphorescent emission from such triplets at room temperature. Accordingly, OLEDs comprising such complexes have been shown to have internal quantum efficiencies of more than 75% (Adachi, et al., Appl. Phys. Lett., 2000, 77, 904). Certain organometallic iridium complexes have been reported as having intense phosphorescence (Lamansky, et al., Inorganic Chemistry, 2001, 40, 1704), and efficient OLEDs emitting in the green to red spectrum have been prepared with these complexes (Lamansky, et al., J. Am. Chem. Soc., 2001, 123, 4304). Red-emitting devices containing iridium complexes have been prepared according to U.S. Pat. No. 6,821,645. Phosphorescent heavy metal organometallic complexes and their respective devices have also been the subject of International Patent Application Publications WO 00/57676, WO 00/70655, and WO 01/41512; U.S. Publications 2006/0202194 and 2006/0204785; and U.S. Pat. Nos. 7,001,536; 6.911,271; 6,939,624; and 6,835,469.
wherein n is 1, 2 or 3; each of R1, R2, and R3 is independently a hydrogen, or a mono-, di-, tri-, tetra-, or penta-substitution of alkyl or aryl; at least one of R1, R2, and R3 is a branched alkyl containing at least 4 carbon atoms, and wherein the branching occurs at a position further than the benzylic position; and X—Y is an ancillary ligand. The branched alkyl can be an isobutyl group. The X—Y ligand can be acac. Specific exemplary compounds are also provided.
Numerous Ir(2-phenylquinoline) and Ir(1-phenylisoquinoline) type phosphorescent materials have been synthesized, and OLEDs incorporating them as the dopant emitters have been fabricated. The devices may advantageously exhibit high current efficiency, high stability, narrow emission, high processibility (such as high solubility and low evaporation temperature), high luminous efficiency, and/or high luminous efficiency: quantum efficiency ratio (LE:EQE).
Together, X and Y represent a bidentate ligand. Numerous bidentate ligands are known to those skilled in the art and many suitable examples are provided in Cotton and Wilkinson, Advanced Inorganic Chemistry, Fourth Ed., John Wiley & Sons, New York, 1980. In some embodiments, bidentate ligands are monoanionic. Suitable bidentate ligands include, but are not limited to, acetylacetonate (acac), picolinate (pic), hexafluoroacetylacetonate, salicylidene, 8-hydroxyquinolinate; amino acids, salicylaldehydes, and iminoacetonates. In one embodiment, X—Y is acac. Bidentate ligands also include biaryl compounds. In some embodiments, the biaryl compounds coordinate to the metal atom through a carbon atom and a nitrogen atom. As used herein, the term “biaryl” refers to compounds comprising two aryl groups covalently joined by a single bond. The aryl groups of a biaryl compound can be aryl or heteroaryl, including both monocyclic or poly-cyclic aryl and heteroaryl groups. Exemplary biaryl groups include, but are not limited to, biphenyl, bipyridyl, phenylpyridyl, and derivatives thereof. Biaryl compounds can serve as bidentate ligands in metal coordination complexes, for instance, by coordinating though one atom in each of the two aryl groups. The coordinating atoms can be carbon or a heteroatom. Further suitable bidentate ligands include, but are not limited to, 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, coumarin, thienylpyridine, phenylpyridine, benzothienylpyridine, 3-methoxy-2-phenylpyridine, thienylpyridine, tolylpyridine, phenylimines, vinylpyridines, arylquinolines, pyridylnaphthalenes, pyridylpyrroles, pyridylimidazoles, phenylindoles, and derivatives thereof. Suitable bidentate ligands also include those provided by U.S. Pat. Nos. 7,001,536; 6,911,271; 6,939,624; and 6,835,469.
Some of the compounds provided comprise at least one bidentate phenylquinolinato (pq) ligand. The term phenylquinolinato, or pq, as used herein refers to both substituted and non-substituted ligands, and the number (n) of coordinated pq ligands can be 1, 2, or 3. In some embodiments, compounds comprise m-1 pq ligands (wherein m is the formal charge of the metal) or, in some embodiments, two pq ligands. Phenylquinolinato ligands can be substituted with substituents R1, R2, and R3 as defined above. Any combination of substituents is suitable. Adjacently-positioned substituents can, together, comprise a 4- to 7-member cyclic group that is fused to the ligand. For example, the pairs R1 and R2 or R2 and R3 can comprise a fused cyclic group. The phrase “fused cyclic group” refers to a cyclic group that shares one or more bonds with a further cyclic group. The pq ligands can have any number of fused cyclic group substituents. Any feasible combination of fused cyclic groups and the remaining of R1, R2, and R3 not involved in a fused cyclic group is contemplated.
Some of the compounds provided can be photoluminescent. In some embodiments, the compounds are efficient phosphors having, for example, a significant portion of luminescence arising from phosphorescent emission. In some embodiments, the emission can be red or reddish. Color of emission can be estimated from the photoluminescence spectrum. A luminescence maximum of about 550 to about 700 nm can indicate red or reddish emission. A maximum at lower wavelengths can indicate green or blue emission. Additionally, the color of emission can be described by color index coordinates x and y (Commision Internationale de L'Eclairage (CIE) 1931 standard 2-degree observer, see, e.g., Shoustikov, et al., IEEE Journal of Selected Topics in Quantum Electronics, 1998, 4, 3; Dartnall, et al., Proceedings of the Royal Society of London B, 1983, 220, 115; Gupta, et al., Journal of Photochemistry, 1985, 30, 173; Colorimetry, 2.sup.nd ed., Publication CIE 15.2-1986 (ISBN 3-900-734-00-3)). For example, a compound emitting in the reds can have coordinates of about 0.5 to about 0.8 for x and about 0.2 to about 0.5 for y.
Processes for preparing compounds are also provided. Phenylquinolinato ligands (L) having desired substitutions can be made using the general procedure of coupling phenyl boronic acid having desired substitution with chloroquinoline (e.g., 2-chloroquinoline, 3-chloroisoquinoline, or 2-chloroisoquinoline) also having desired substitution. Coupling procedures can be, for example, conducted under Suzuki conditions in the presence of palladium(II) (see, e.g., Miyaura, et al., Chem. Rev. 1995, 2457). The quinoline (or isoquinoline) and boronic acid starting materials can be obtained from commercial sources or synthesized by methods known in the art. For example, 3-chloroisoquinoline can be made according to the procedures described in Haworth, R. D., et al., J Chem. Soc., 1948, 777.
Some of the compounds provided can be used as emitters in organic light emitting devices. Accordingly, the compounds can be present in an emissive layer (i.e., a layer from which light is primarily emitted) of a such device. The emissive layer can be, for example, a layer consisting essentially of one or more of the compounds provided. Some of the compounds provided can also be present as dopants. For example, an emissive layer can comprise host material doped with one or more of the compounds provided. The host material can comprise any compound, including organic and organometallic compounds, suitable in an emissive layer in an OLED. Exemplary organic host materials include, but are not limited to, BCP (bathocuproine or 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), CBP (4,4′-N,N′-dicarbazole biphenyl), OXD7 (1,3-bis(N,N-t-butylphenyl)-1,3,4-oxadiazole), TAZ (3-phenyl-4-(1′-naphthyl)-5-phenyl-1,2,4-triazole), NPD (4,4′-bis[N-(1-naphthyl)-N-phenyl-amino]biphenyl), CuPc (copper phthalocyanine), Alq3 (aluminum tris(8-hydroxyquinolate)), and BAlq ((1,1′-biphenyl)-4-olato)bis(2-methyl-8-quinolinolato N1,O8)aluminum). Other materials that can be included in an emissive layer in addition to the emissive compounds include Irppy (tris(2-phenylpyridinato-N,C2′)iridium(III)), FIrpic (bis(2-(4,6-difluorophenyl)pyridinato-N,C2′)iridium(III(picolinate)), and other metal complexes such as those described in U.S. Pat. Nos. 7,001,536; 6,911,271; and 6,939,624. As dopants, some of the compounds provided can be present in the emissive layer, such as in host material, in amounts of about 1 to about 20 wt %, about 5 to about 15 wt %, about 5 to about 10 wt %, or other similar ranges.
70° C. Lifetime comparison Tsubl at EML At 10 mA/cm2 T80% at 40 mA/cm2 (hr) (L0)2(T80%)
0.24 Å/s dopant λ FWHM V LE EQE LE: L0 at 70° C. Dopant (° C.) % max (nm) CIE (V) (cd/A) (%) EQE (cd/m2) RT 70° C. (×109)
Comp. 206 12 622 94 0.65 8.1 14.3 14 1.01 4817 991 60 1.39 Ex. 1 0.35 Comp. 229 9 630 84 0.68 9.1 11.1 15 0.72 3808 1200 180 2.61 Ex. 2 0.32 1 192 12 622 66 0.67 8.8 18.3 17.7 1.03 6382 n.m. 73 2.97 0.33 2 220 12 634 82 0.68 8.9 9.6 13.5 0.71 3308 n.m. 127 1.39 0.32 3 200 12 632 80 0.68 8.8 10.8 15.6 0.69 3784 n.m. 145 2.08 0.32 4 186 12 630 82 0.68 9.49 11.07 16 0.69 3852 n.m. 132 1.96 0.32 5 206 12 626 82 0.66 8.8 14.6 16.1 0.91 5175 n.m. 55 1.47 0.33 6 207 12 628 86 0.67 9 11.2 15.3 0.73 4007 n.m. 127 2.04 0.32 7 202 12 626 83 0.66 8.6 14.3 14 1.02 4877 n.m. 127 3.02 0.34 8 177-185 12 636 70 0.69 8.6 9.8 14.6 0.67 3390 n.m. 38 0.44 0.31 9 163-172 12 618 61 0.66 9.2 23.5 18.8 1.25 7992 n.m. 60 3.83 0.34 13 211 12 618 78 0.65 9.1 20.1 17.2 1.17 6865 n.m. 52 2.45 0.35 14 212 12 632 80 0.67 9.6 7.9 10.1 0.78 2810 n.m. 32 0.25 0.33 15 217 12 622 66 0.665 8.9 18.6 17.5 1.06 6411 n.m. 40 1.64 0.333 16 186 12 618 65 0.658 9.8 22.4 18.7 1.20 7593 n.m. 10.6 0.61 0.340 20 210 12 620 79 0.655 8.7 16.8 15.4 1.09 6026 n.m. 80 2.91 0.347 22 210 12 637 66 0.693 9.5 9.8 17.5 0.56 3277 n.m. 80 0.86 0.304 24 218 12 635 66 0.691, 8.9 11.5 19.0 0.61 3894 n.m. 90 1.36 0.306 n.m. = not measured
Tsubl at At 10 mA/cm2 T80% at 40
0.24 Å/s λ FWHM V LE EQE LE: L0 mA/cm2 (hr)
Dopant (° C.) max (nm) CIE (V) (cd/A) (%) EQE (cd/m2) RT 70° C.
Comp. 200-210 602 78 0.61 8.5 27.1 16.6 1.63 9370 200 n.m. Ex. 3 0.38 Comp. 237 618 78 0.65 8 9.8 8.8 1.11 3622 530 n.m. Ex. 4 0.34 1 192 622 66 0.67 8.8 18.3 17.7 1.03 6382 n.m. 73 0.33 Comp. 229 632 84 0.68 8.8 10.6 15.2 0.70 3757 n.m. 240 Ex. 5 0.32 22 210 637 66 0.693 9.5 9.8 17.5 0.56 3277 n.m. 80 0.304
Comp. 190 618 64 0.66 8.7 20 16.8 1.19 7014 n.m. 31 Ex. 6 0.34 9 198 618 61 0.66 9.2 23.5 18.8 1.25 7992 n.m. 60 0.34 16 186 618 65 0.658 9.8 22.4 18.7 1.20 7593 n.m. 10.6 0.340 20 210 620 79 0.655 8.7 16.8 15.4 1.09 6026 n.m. 80 0.347 Comp. 237 618 78 0.65 8 9.8 8.8 1.11 3622 530 n.m. Ex. 7 0.34
DME 1,2-dimethoxyethane Pd2(dba)3 Tris(dibenzylideneacetone)dipalladium Pd(OAc)2 Palladium acetate Pd(PPh3)4 Tetrakis(triphenylphosphine)palladium Ph3P Triphenylphosphine RuCl2(PPh3)3 Dichlorotris(triphenylphosphine)ruhenium (III) THF Tetrahydrofuran
To a 500 mL round bottle flask, 9.0 g (˜54.4 mmol) of 2-chloroquinoline, 9.2 g (59.8 mmol) of 3,5-dimethylphenylboronic acid, 1.8 g (1.5 mmol) of Pd(PPh3)4, 22.4 g (163 mmol) of K2CO3, 150 mL of DME, and 150 mL of water were charged. The reaction mixture was heated to reflux under nitrogen overnight. The reaction mixture was cooled, and the organic extracts were purified by a silica gel column chromatography (10% ethyl acetate in hexane as eluent). The material obtained was further purified by vacuum distillation (Kugelrohr) at 185° C. to yield 12.2 g (95% yield) of product as a colorless liquid.
6.2 g of 7-isopropyl-1-phenyl-3,4-dihydroisoquinoline and 1 g of 5% Pd/C (˜10% by weight) were added to a round-bottom flask with 100 mL of xylenes. The solution was refluxed for 24 hrs, and the formation of the product was monitored by TLC. The xylenes solvent was removed, and the product was purified by column chromatography with ethyl acetate/hexanes. The pure fractions were collected, and the solvent was removed. The product was then distilled in a Kugelrohr apparatus at 185° C. affording 1.8 g (0.0073 mol) of pure product. The overall yield of ligand formation was ˜15%.
4-bromoisoquinoline (15 g, 72.5 mmol), methylboronic acid (8.8 g, 145 mmol), K1PO4 (62 g, 290 mmol), Pd2(dba)3 (6.6 g, 7.2 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (5.9 g, 14.4 mmol, 0.2 equiv), and 350 mL of anhydrous toluene were charged to a dry 500 mL three-neck flask. The mixture was refluxed under nitrogen for 20 hrs. After cooling, 200 mL of methylene chloride was added. The mixture was filtered to remove insolubles, then concentrated under vacuum. The resulting crude material was distilled at 130° C. (first fraction at 95° C. was discarded). Approximately 9.8 g of a colorless liquid was obtained (94% yield). The product was used for the next step without further purification (96% product, 3.5% isoquinoline).
Lithium aluminum hydride (2.65 g, 69.8 mmol) was added to 80 mL of THF that was cooled in an ice bath. A solution of 2-amino-6-fluorobenzoic acid (10 g, 64.46 mmol) in 50 mL THF was added dropwise via a dropping funnel. The reaction was allowed to stir overnight at room temperature. Another portion of 20 mL of IM lithium aluminum hydride in THF was added, and the reaction was heated to 40° C. Upon cooling in an ice bath, 3 mL of water was added carefully via a dropping funnel followed by 50 mL of 1N NaOH, and the mixture was stirred for 15 min. Next, 50 mL of water was added, and the mixture was stirred for 10 min. More NaOH solution was added, and the emulsion was stirred overnight. The organic layers were extracted, washed with water, and concentrated, and the residue was dissolved in 100 mL of ethyl acetate. Hexanes were added, and a solid precipitated out and was filtered to yield 3.66 g of a tan solid, which was used for the next step.
The dimer was mixed with 2,4-pentanedione (5.5 mL, 53 mmol), K2CO3 (1.23 g. 8.90 mmol), and 2-ethoxyethanol (100 mL) and heated to 110° C. under nitrogen for 1 day. The cooled mixture was filtered, and the red solid was rinsed with isopropanol. The solid was dissolved in dichloromethane and purified on a silica gel plug. The plug was treated with 10% triethylamine/hexanes followed by hexanes prior to loading the material, and the product was eluted with dichloromethane. The fractions with product were collected and concentrated to a small volume. Isopropanol was added, and the mixture was concentrated. The precipitated solid was filtered and purified by two sublimations to yield 3.73 g of product.
2-xylyl-7-chloroquinoline (3.0 g, 11 mmol) from Step 2 of Compound 9 and iron(III) acetylacetonate (0.2 g, 0.56 mmol) were dissolved in 66 mL of a solution of THF/l-methyl-2-pyrrolidinone (60/6) in a 250 mL round-bottom flask. Nitrogen was bubbled through the reaction mixture for 10 min. The solution was cooled using an ice bath. 11.2 mL of 2.0M isopropylmagnesium chloride in ether was added dropwise. The reaction was stirred for 2 hrs and then quenched slowly with water. The reaction mixture was allowed to warm to room temperature, and ethyl acetate was added. The organic phase was washed with water and dried over magnesium sulfate. The solvent was removed under vacuo, and the product was chromatographed using a silica gel column with 2% ethyl acetate in hexanes as the eluent to give 2 g (67% yield) of product.
0.6 g the dimer, 2,4-pentanedione (0.37 g, 3.5 mmol), and K2CO3 (0.38 g, 3.5 mmol) were added to 50 mL of 2-methoxyethanol and stirred at room temperature for 24 hrs. The precipitate was filtered and washed with methanol. The solid was redissolved in dichloromethane and passed through a plug with Celite, silica gel, and basic alumina. The solvent was evaporated under vacuum to give ˜0.45 g (69% yield) of product.
The dimer (3.0 g, 1.8 mmol), 2,4-pentanedione (1.8 g, 18.0 mol), and K2CO3 (3.0g, 18.0 mmol) were added to 100 mL of 2-methoxyethanol and stirred at room temperature for 24 hrs. The precipitate was filtered and washed with methanol. The solid was redissolved in dichloromethane and passed through a plug with Celite, silica gel, and basic alumina. The solvent was evaporated under vacuum to give 2.0 g of product.
2-(3propylphenyl)quinoline (3.2 g, 13.0 mmol) and iridium(III) chloride (1.8 g, 5.2 mmol) were dissolved in 50 mL of a 3:1mixture of 2-ethoxyethanol and water, respectively, in a 100 mL round-bottom flask. Nitrogen was bubbled through the solution for 10 min and then refluxed under nitrogen for 16 hrs. The reaction mixture was then allowed to cool to room temperature, and the precipitate was filtered and washed with methanol. The dimer was then dried under vacuum and used for next step without further purification. 2.6 g of the dimer was obtained after vacuum drying.
Dichloroiodobenzene (37.0 g 136 mmol), Pd2(dba)3 (1.5 g, 1.6 mmol), and lithium chloride (29.0 g, 682 mmol) were dissolved in 100 mL of DMF in a 500 mL round-bottom flask. 64.0 mL of acetic anhydride and 47.0 mL of N-ethyldiisopropylamine were then added to the reaction mixture. The reaction was heated to 100° C. for 8 hrs. Water was added to the reaction mixture, and the product was extracted with ethyl acetate and chromatographed using a silica gel column with ethyl acetate and hexanes as the eluent. 8 g of product was obtained.
1a ITO/Compound A (100 Å)/NPD (400 Å)/BAlq:Compound 1 (6%) (300 Å)/Alq3 (550 Å)/LiF/Al 1b ITO/Compound A (100 Å)/NPD (400 Å)/BAlq:Compound 1 (9%) (300 Å)/Alq3 (550 Å)/LiF/Al 1c ITO/Compound A (100 Å)/NPD (400 Å)/BAlq:Compound 1 (12%) (300 Å)/Alq3 (550 Å)/LiF/Al 1d ITO/Compound A (100 Å)/NPD (400 Å)/BAlq:Compound A (10%):Compound 1 (3%) (300 Å)/Balq (100)/Alq3 (450 Å)/ LiF/Al 1e ITO/Compound A (100 Å)/NPD (400 Å)/Compound B: Compound 1 (12%) (300 Å)/Alq3 (550 Å)/LiF/Al 1f ITO/Compound A (100 Å)/NPD (100 Å)/Compound B: Compound 1 (12%) (300 Å)/Compound B (100 Å)/Alq3 (450 Å)/LiF/Al 1g ITO/Compound A (100 Å)/NPD (400 Å)/Compound C: Compound 1 (6%) (300 Å)/Alq3 (550 Å)/LiF/Al 1h ITO/Compound A (100 Å)/NPD (400 Å)/Compound C: Compound 1 (9%) (300 Å)/Alq3 (550 Å)/LiF/Al 1i ITO/Compound A (100 Å)/NPD (400 Å)/Compound C: Compound 1 (12%) (300 Å)/Alq3 (550 Å)/LiF/Al
T80% at 40
EML mA/cm2 (hr)
dop- At 500 nits L0
De- ant λ V LE EQE (cd/ 70° vice % max CIE (V) (cd/A) (%) m2) RT C.
9a ITO/Compound A (100 Å)/NPD (400 Å)/BAlq:Compound 9 (6%) (300 Å)/Alq3 (550 Å)/LiF/Al 9b ITO/Compound A (100 Å)/NPD (400 Å)/BAlq:Compound 9 (9%) (300 Å)/Alq3 (550 Å)/LiF/Al 9c ITO/Compound A (100 Å)/NPD (400 Å)/BAlq:Compound 9 (12%) (300 Å)/Alq3 (550 Å)/LiF/Al 9d ITO/Compound A (100 Å)/NPD (400 Å)/BAlq:Compound A (10%):Compound 9 (3%) (300 Å)/Balq (100)/Alq3 (450 Å)/ LiF/Al 9e ITO/Compound A (100 Å)/NPD (400 Å)/BAlq:Compound A (10%):Compound 9 (3%) (300 Å)/Alq3 (550 Å)/LiF/Al 9f ITO/Compound A (100 Å)/NPD (400 Å)/Compound C: Compound 9 (9%) (300 Å)/Compound C (100 Å)/Alq3 (450 Å)/LiF/Al 9g ITO/Compound A (100 Å)/NPD (400 Å)/Compound C: Compound 9 (9%) (300 Å)/BAlq (100 Å)/Alq3 (450 Å)/ LiF/Al 9h ITO/Compound A (100 Å)/NPD (400 Å)/Compound C: Compound 9 (9%) (300 Å)/Alq3 (550 Å)/LiF/Al 9i ITO/Compound A (100 Å)/NPD (400 Å)/Compound C: Compound A (10%):Compound 9 (3%) (300 Å)/Compound C (100 Å)/Alq3 (450 Å)/LiF/Al 9j ITO/Compound A (100 Å)/NPD (400 Å)/Compound C: Compound A (10%):Compound 9 (3%) (300 Å)/BAlq (100 Å)/ Alq3 (450 Å)/LiF/Al 9k ITO/Compound A (100 Å)/NPD (400 Å)/Compound C: Compound A (10%):Compound 9 (3%) (300 Å)/Alq3 (550 Å)/ LiF/Al
dop- At 1000 nits L0
22a ITO/Compound A (100 Å)/NPD (400 Å)/BAlq:Compound 22 (6%) (300 Å)/Alq3 (550 Å)/LiF/Al 22b ITO/Compound A (100 Å)/NPD (400 Å)/BAlq:Compound 22 (9%) (300 Å)/Alq3 (550 Å)/LiF/Al 22c ITO/Compound A (100 Å)/NPD (400 Å)/BAlq:Compound 22 (12%) (300 Å)/Alq3 (550 Å)/LiF/Al 22d ITO/Compound A (100 Å)/NPD (400 Å)/BAlq:Compound A (10%):Compound 22 (3%) (300 Å)/Balq (100)/Alq3 (450 Å)/LiF/Al
wherein each R1, R2, and R3 is independently selected from the group consisting of hydrogen, alkyl, and aryl;
wherein at least one of R1 and R2 is a branched alkyl containing at least 4 carbon atoms, and
wherein the branching occurs at a position further than the benzylic position;
wherein R1 and R3 are mono-, di-, tri-, tetra-, or no substitutions;
wherein R2 is mono-, di-, or no substitutions; and
2. The compound of claim 1, wherein at least one of R1 and R2 is an isobutyl group.
3. The compound of claim 1, wherein X—Y is acac.
4. The compound of claim 1, having a structure of the formula:
5. The compound of claim 1, having a structure of the formula:
wherein R1 and R3 are mono-, di-, tri-, tetra-, or no substitutions; and
wherein R2 is mono-, di-, or no substitutions.
9. The compound of claim 6, including a ligand having a structure of the formula:
10. The compound of claim 6, including a ligand having a structure of the formula:
an emissive organic layer, disposed between the anode and the cathode, wherein the organic layer comprises an iridium compound having the formula:
12. The device of claim 11, wherein the organic emissive layer further comprises BAlq or
13. The device of claim 12, wherein the compound is: and the organic emissive layer comprises BAlq.
14. The device of claim 12, wherein the compound is and the organic emissive layer comprises
15. The device of claim 11, wherein at least one of R1 and R2 is an isobutyl group.
16. The device of claim 11, wherein X—Y is acac.
17. The device of claim 11, wherein the compound has a structure of the formula:
18. The device of claim 11, wherein the compound has a structure of the formula:
9034483 May 19, 2015 Alleyne
9142786 September 22, 2015 Kwong
20030151042 August 14, 2003 Hueschen
20040100189 May 27, 2004 Adachi et al.
20060204785 September 14, 2006 Kim et al.
1589307 March 2005 CN
1348711 October 2003 EP
H09-279136 October 1997 JP
2003073387 March 2003 JP
100662379 January 2007 KR
0139234 May 2001 WO
0202714 January 2002 WO
03033617 April 2003 WO
03040256 May 2003 WO
2005/124889 December 2005 WO
2006014599 February 2006 WO
2006035997 April 2006 WO
2009021126 May 2009 WO
Adachi, Chihaya et al., “Nearly 100% Internal Phophorescence Efficiency in an Organic Light Emitting Device,” J. Appl. Phys., 90(10): 5048-5051 (2001).
Gao, Zhiqiang et al., “Bright-Blue Electroluminesence From a Silyl-Substituted ter-(phenylene-vinlylene) derivative,” Appl. Phys. Lett., 74(6): 865-867 (1999).
Hamada, Yuji et al., “High Luminance in Organic Electroluminescent Devices with Bis(10-hydroxybenzo[h]quinolinato)beryllium as an Emitter,” Chem. Lett., 905-906 (1993)
Ikeda, Hisao et al., “P-185 Low Drive-Voltage OLEDs with a Buffer Layer Having Molybdenum Oxide,” SID Symposium Digest, 37:923-926 (2006).
Kuwabara, Yoshiyuki et al., “Thermally Stable Multilayered Organic Electroluminescent Devices Using Novel Starbust Molecules, 4,4′,4″-Tri(N-carbazolyl)triphenylamine (TCTA) AND 4,4′,4″-Tris(3-methylphenylphenyl-amino)triphenylamine (m-MTDATA), as Hole-Transport Materials,” Adv. Mater., 6(9):677-679 (1994).
Shirota, Yasuhiko et al.; “Starburst Molecules Based on p-Electron Systems as Materials for Organic Electroluminescent Devices,” Journal of Luminescence, 72-74:985-991 (1997).
Sotoyama, Wataru et al., “Eificient Organic Light-Emitting Diodes with Phosphorescent Platinum Complexes Containing NCN-Coordinating Tridentate Ligand,” Appl. Phys. Lett., 86:153505-1-153505-3 (2005).
Sun, Yiru and Forrest, Stephen R., “High-Efficiency White Organic Light Emitting Device with Three Separate Phosphorescent Emission Layers,” Appl. Phys. Lett., 91:263503-1-263503-3 (2007).
Tang, C.W.and VanSlyke, S.A., “Organic Electroluminescent Diodes,” Appl. Phys. Lett., 51(12):913-915 (1987).
State Intellectual Property Office of the People's Republic of China, Notification and English Version of Chinese Office Action regarding corresponding Chinese Application No. 201210371182.4 issued Jan. 9, 2015, pp. 1-9.
State Intellectual Property Office of the People's Republic of China, Chinese Search Report and English Abstract regarding corresponding Chinse Application No. 201210371182.4 issued Jan. 9, 2015, pp. 1-4.
Foreign Office Action dated Mar. 4, 2014 for corresponding Chinese Application No. 201210371182.4.
Notice for Reasons for Rejection issued Aug. 14, 2014 for corresponding Japanese Application No. 2013-179125.
Notice of Reasons for Rejection issued on Feb. 3, 2016 in corresponding JP Patent Application No. 2015-027185.
Search Report issued on May 26, 2016 for corresponding Taiwanese Patent Application No. 104127056.
Communication pursuant to Article 94(3) EPC issued Sep. 25, 2015 for corresponding EP Patent Application No. 12159690.2.
Patent number: 9577201
Patent Publication Number: 20150357588
Inventors: Raymond Kwong (Plainsboro, NJ), Bin Ma (Plainsboro, NJ), Chuanjun Xia (Lawrenceville, NJ), Bert Alleyne (Ewing, FL), Jason Brooks (Philadelphia, PA)
Application Number: 14/826,762
International Classification: H01L 51/54 (20060101); C09K 11/06 (20060101); H01L 51/00 (20060101); C07F 15/00 (20060101); H05B 33/14 (20060101); H01L 51/50 (20060101);