Compositions with Triarylamine Derivatives and Oled Device Containing the Same

Abstract

The present disclosure provides a composition. In an embodiment, a composition is provided and comprises a Compound 1 shown below: For Compound 1, R.sub.1 through R.sub.24 are the same or different. R.sub.1 through R.sub.24 each is independently selected from the group consisting of hydrogen, unsubstituted hydrocarbyl, substituted hydrocarbyl, cyano, alkoxy, aryloxy, and NR′.sub.2. R′ is hydrogen or hydrocarbyl; wherein two or more of adjacent R.sub.1 to R.sub.24 may optionally form one or more ring structures. The Component Z is selected from the group consisting Group Z-1, Group Z-2, Group Z-3, Group Z-4, Group Z-5, Group Z-6 and Group Z-7 shown below: For Compound 1, one or more hydrogen atoms may optionally be substituted with deuterium.

##STR00001##

Claims

1. A composition comprising a Compound 1: ##STR00038## wherein R.sub.1 through R.sub.24 are the same or different and each of R.sub.1 through R.sub.24 is independently selected from the group consisting of hydrogen, unsubstituted hydrocarbyl, substituted hydrocarbyl, cyano, alkoxy, aryloxy, and NR′.sub.2; wherein R′ is hydrogen or hydrocarbyl; wherein two or more of adjacent R.sub.1 to R.sub.24 may optionally form one or more ring structures; and Z is selected from the group consisting Group Z-1, Group Z-2, Group Z-3, Group Z-4, Group Z-5, Group Z-6, and Group Z-7 shown below ##STR00039## wherein, for Compound 1, one or more hydrogen atoms may optionally be substituted with deuterium.

2. The composition of claim 1, wherein R.sub.1 through R.sub.24 each is independently selected from the group consisting of hydrogen, unsubstituted hydrocarbyl and substituted hydrocarbyl.

3. The composition of claim 2, wherein R.sub.1 through R.sub.24 each is hydrogen.

4. The composition of claim 2, wherein Compound 1 has a HOMO level from −4.50 eV to −4.90 eV.

5. The composition of claim 2, wherein Compound 1 has a LUMO level from 0.00 eV to −1.10 eV.

6. The composition of claim 2, wherein Compound 1 has a triplet energy level from 2.50 eV to 3.30 eV.

7. The composition of claim 2, wherein Compound 1 has a molecular weight from 500 g/mole to 1000 g/mole.

8. The composition of claim 2, wherein Compound 1 has a glass transition temperature, Tg, from 110° C. to 180° C., as determined by DSC.

9. The composition of claim 1, wherein R.sub.1 through R.sub.24 each is independently selected from the group consisting of hydrogen, unsubstituted hydrocarbyl, and substituted hydrocarbyl; and Component Z for Compound 1 comprises Group Z-1 as shown below ##STR00040##

10. The composition of claim 9, wherein Compound 1 has the Structure (i) as shown below ##STR00041##

11. The composition of claim 10, wherein Structure (i) has a HOMO level from −4.50 eV to −4.90 eV.

12. The composition of claim 11, wherein Structure (i) has a LUMO level from 0.00 eV to −1.10 eV.

13. The composition of claim 12, wherein Structure (i) has a triplet energy level from 2.50 to 3.30 eV.

14. A film formed from the composition of claim 1.

15. An electronic device comprising at least one component formed from the composition of claim 1.

Description

DETAILED DESCRIPTION

[0034] 1. Composition

[0035] The present disclosure provides a composition. The composition includes Compound 1. The structure for Compound 1 is provided below.

##STR00004##

[0036] For Compound 1, R.sub.1 through R.sub.24 are the same or different and each of R.sub.1 through R.sub.24 is independently selected from hydrogen, unsubstituted hydrocarbyl, substituted hydrocarbyl, a cyano, alkoxy, aryloxy, and NR′.sub.2. Two or more of adjacent R.sub.1 to R.sub.24 may optionally form one or more ring structures.

[0037] For the NR′.sub.2 moiety of Compound 1, R′ is hydrogen or hydrocarbyl.

[0038] For Compound 1, Component Z is selected from Group Z-1, Group Z-2, Group Z-3, Group Z-4, Group Z-5, Group Z-6, and Group Z-7. The structures for Groups Z-1, Z-2, Z-3, Z-4, Z-5, Z-6, and Z-7 are provided below:

##STR00005##

[0039] For Compound 1, one, some, or all hydrogen atoms optionally may be substituted with deuterium.

[0040] In an embodiment, Compound 1 includes Group Z-1 (below).

##STR00006##

[0041] In an embodiment, Compound 1 includes Group Z-2 (below).

##STR00007##

[0042] In an embodiment, Compound 1 includes Group Z-3 (below).

##STR00008##

[0043] In an embodiment, Compound 1 includes Group Z-4 (below).

##STR00009##

[0044] In an embodiment, Compound 1 includes Group Z-5 (below).

##STR00010##

[0045] In an embodiment, Compound 1 includes Group Z-6 (below).

##STR00011##

[0046] In an embodiment, Compound 1 includes Group Z-7 (below).

##STR00012##

[0047] In an embodiment, Compound 1 has a purity greater than 99 percent (%) as determined by analytical methods, for example, high-performance liquid chromatography (HPLC), liquid chromatography (LC), and/or liquid chromatography-mass spectrometry (LC-MS or HPLC-MS).

[0048] In an embodiment, for Compound 1, R.sub.1 through R.sub.24 each is independently selected from following: hydrogen, unsubstituted hydrocarbyl and substituted hydrocarbyl.

[0049] In an embodiment, for Compound 1, R.sub.1 through R.sub.24 each is hydrogen.

[0050] In an embodiment, Compound 1 has a HOMO level from −4.50 eV, or −4.55 eV, or −4.60 eV to −4.80 eV, or −4.85 eV, or −4.90 eV.

[0051] In an embodiment, Compound 1 has a LUMO level from 0.00 eV, or −0.20 eV, or −0.50 eV to −1.00 eV, or −1.05 eV, or −1.10 eV.

[0052] In an embodiment, Compound 1 has a triplet energy level from 2.50 eV, or 2.90 eV to 3.10 eV, or 3.30 eV.

[0053] In an embodiment, Compound 1 has a molecular weight from 500 grams/mole (g/mol), or 550 g/mol, or 600 g/mol, or 650 g/mol, or 700 g/mol to 800 g/mol, or 850 g/mol, or 900 g/mol, or 950 g/mol, or 1000 g/mol.

[0054] In an embodiment, Compound 1 has a Tg from 110° C., or 120° C., or 130° C., or 140° C., or 150° C. to 160° C., or 170° C., or 180° C., as determined by DSC.

[0055] A. Group Z-1

[0056] In an embodiment, the composition includes Compound 1, and R.sub.1 through R.sub.24 each is independently selected from hydrogen, unsubstituted hydrocarbyl, and substituted hydrocarbyl. Component Z for Compound 1 includes Group Z-1 as shown below:

##STR00013##

[0057] In an embodiment, Compound 1 with Group Z-1 has a molecular weight (MW) from 690 g/mole to 900 g/mole.

[0058] In an embodiment, the composition includes Compound 1 with Group Z-1, and Compound 1 has the Structure (i) below:

##STR00014##

[0059] In an embodiment, Structure (i) has a HOMO level from −4.50 eV to −4.90 eV.

[0060] In an embodiment, Structure (i) has a LUMO level from 0.00 eV to −1.10 eV.

[0061] In an embodiment, Structure (i) has a triplet energy level from 2.50 eV to 3.30 eV.

[0062] In an embodiment, the Structure (i) has a glass transition temperature, Tg, from 110° C. to 180° C., as determined by DSC.

[0063] B. Group Z-2

[0064] In an embodiment, the composition includes Compound 1, and R.sub.1 through R.sub.24 each is independently selected from hydrogen, unsubstituted hydrocarbyl, and substituted hydrocarbyl. Component Z for Compound 1 is Group Z-2 below:

##STR00015##

[0065] In an embodiment, Compound 1 with Group Z-2 has a molecular weight from 738 g/mole to 900 g/mole.

[0066] In an embodiment, the composition includes Compound 1 with Group Z-2, and Compound 1 has the Structure (ii) below:

##STR00016##

[0067] In an embodiment, Structure (ii) has a HOMO level from −4.50 eV to −4.90 eV.

[0068] In an embodiment, Structure (ii) has a LUMO level from 0.00 eV to −1.10 eV.

[0069] In an embodiment, Structure (ii) has a triplet energy level from 2.50 eV to 3.30 eV.

[0070] In an embodiment, the Structure (ii) has a glass transition temperature, Tg, from 110° C. to 180° C., as determined by DSC.

[0071] C. Group Z-3

[0072] In an embodiment, the composition includes Compound 1, and R.sub.1 through R.sub.24 each is independently selected from hydrogen, unsubstituted hydrocarbyl, and substituted hydrocarbyl. Component Z for Compound 1 is Group Z-3 below:

##STR00017##

[0073] In an embodiment, Compound 1 with Group Z-3 has a molecular weight from 694 g/mole to 900 g/mole.

[0074] In an embodiment, the composition includes Compound 1 with Group Z-3, and Compound 1 has the Structure (iii) below:

##STR00018##

[0075] In an embodiment Structure (iii) has a HOMO level from −4.50 eV to −4.90 eV.

[0076] In an embodiment, structure (iii) has a LUMO level from 0.00 eV to −1.10 eV.

[0077] In an embodiment, Structure (iii) has a triplet energy level from 2.50 eV to 3.30 eV.

[0078] In an embodiment, the Structure (iii) has a glass transition temperature, Tg, from 110° C. to 180° C., as determined by DSC.

[0079] D. Group Z-4

[0080] In an embodiment, the composition includes Compound 1, and R.sub.1 through R.sub.24 each is independently selected from hydrogen, unsubstituted hydrocarbyl, and substituted hydrocarbyl. Component Z for Compound 1 is Group Z-4 below:

##STR00019##

[0081] In an embodiment, Compound 1 with Group Z-4 has a molecular weight from 694 g/mole to 900 g/mole.

[0082] In an embodiment, Compound 1 with Group Z-4 has a HOMO level from −4.50 eV to −4.90 eV.

[0083] In an embodiment, Compound 1 with Group Z-4 has a LUMO level from 0.00 eV to −1.10 eV.

[0084] In an embodiment, Compound 1 with Group Z-4 has a triplet energy level from 2.50 eV to 3.30 eV.

[0085] In an embodiment, Compound 1 with Group Z-4 has a glass transition temperature, Tg, from 110° C. to 180° C., as determined by DSC.

[0086] E. Group Z-5

[0087] In an embodiment, the composition includes Compound 1, and R.sub.1 through R.sub.24 each is independently selected from hydrogen, unsubstituted hydrocarbyl, and substituted hydrocarbyl. Component Z for Compound 1 is Group Z-5 below:

##STR00020##

[0088] In an embodiment, Compound 1 with Group Z-5 has a molecular weight from 694 g/mole to 900 g/mole.

[0089] In an embodiment, Compound 1 with Group Z-5 has a HOMO level from −4.50 eV to −4.90 eV.

[0090] In an embodiment, Compound 1 with Group Z-5 has a LUMO level from 0.00 eV to −1.10 eV.

[0091] In an embodiment, Compound 1 with Group Z-5 has a triplet energy level from 2.50 eV to 3.30 eV.

[0092] In an embodiment, Compound 1 with Group Z-5 has a glass transition temperature, Tg, from 110° C. to 180° C., as determined by DSC.

[0093] F. Group Z-6

[0094] In an embodiment, the composition includes Compound 1, and R.sub.1 through R.sub.24 each is independently selected from hydrogen, unsubstituted hydrocarbyl, and substituted hydrocarbyl. Component Z for Compound 1 is Group Z-6 below:

##STR00021##

[0095] In an embodiment, Compound 1 with Group Z-6 has a molecular weight from 694 g/mole to 900 g/mole.

[0096] In an embodiment, Compound 1 with Group Z-6 has a HOMO level from −4.50 eV to −4.90 eV.

[0097] In an embodiment, Compound 1 with Group Z-6 has a LUMO level from 0.00 eV to −1.10 eV.

[0098] In an embodiment, Compound 1 with Group Z-6 has a triplet energy level from 2.50 eV to 3.30 eV.

[0099] In an embodiment, Compound 1 with Group Z-6 has a glass transition temperature, Tg, from 110° C. to 180° C., as determined by DSC.

[0100] G. Group Z-7

[0101] In an embodiment, the composition includes Compound 1, and R.sub.1 through R.sub.24 each is independently selected from hydrogen, unsubstituted hydrocarbyl, and substituted hydrocarbyl. Component Z for Compound 1 is Group Z-7 below:

##STR00022##

[0102] In an embodiment, Compound 1 with Group Z-7 has a molecular weight from 694 g/mole to 900 g/mole.

[0103] In an embodiment, Compound 1 with Group Z-7 has a HOMO level from −4.50 eV to −4.90 eV.

[0104] In an embodiment, Compound 1 with Group Z-7 has a LUMO level from 0.00 eV to −1.10 eV.

[0105] In an embodiment, Compound 1 with Group Z-7 has a triplet energy level from 2.50 eV to 3.30 eV.

[0106] In an embodiment, Compound 1 with Group Z-7 has a glass transition temperature, Tg, from 110° C. to 180° C., as determined by DSC.

[0107] In an embodiment, one, some, or all methyl moieties on Groups Z-1 through Z-7 may be replaced by, or otherwise substituted with, an alkyl containing 2, 3, 4, 5, or 6 carbon atoms.

[0108] The present composition may comprise two or more embodiments disclosed herein.

[0109] Compound 1 may comprise two or more embodiments disclosed herein.

[0110] 2. Film

[0111] The present disclosure provides a film. The film includes, or is otherwise formed from, the present composition.

[0112] In an embodiment, the film includes the composition composed of Compound 1. Compound 1 can have any structure previously disclosed herein.

[0113] In an embodiment, the film includes the composition composed of Compound 1. Component Z of Compound 1 is Group Z-1.

[0114] In an embodiment, the film includes the composition composed of Compound 1. Component Z of Compound 1 is Group Z-2.

[0115] In an embodiment, the film includes the composition composed of Compound 1. Component Z of Compound 1 is Group Z-3.

[0116] In an embodiment, the film includes the composition composed of Compound 1. Component Z of Compound 1 is Group Z-4.

[0117] In an embodiment, the film includes the composition composed of Compound 1. Component Z of Compound 1 is Group Z-5.

[0118] In an embodiment, the film includes the composition composed of Compound 1. Component Z of Compound 1 is Group Z-6.

[0119] In an embodiment, the film includes the composition composed of Compound 1. Component Z of Compound 1 is Group Z-7.

[0120] In an embodiment, the film includes the composition composed of one or more Compound 1s, the plurality of Compound 1s having two or more different Z components selected from Group Z-1, Group Z-2, Group Z-3, Group Z-4, Group Z-5, Group Z-6, and Group Z-7 and any combination thereof.

[0121] In an embodiment, the film is formed with an evaporative process.

[0122] In an embodiment, the film is formed in a solution process.

[0123] The present film may comprise two or more embodiments disclosed herein.

[0124] 3. Device

[0125] The present disclosure provides an electronic device. The electronic device includes at least one component that includes, or is otherwise formed from, the present composition.

[0126] In an embodiment, the electronic device includes the composition composed of Compound 1. Compound 1 can have any structure previously disclosed herein.

[0127] In an embodiment, the electronic device includes the composition composed of Compound 1. Component Z of Compound 1 is Group Z-1.

[0128] In an embodiment, the electronic device includes the composition composed of Compound 1. Component Z of Compound 1 is Group Z-2.

[0129] In an embodiment, the electronic device includes the composition composed of Compound 1. Component Z of Compound 1 is Group Z-3.

[0130] In an embodiment, the electronic device includes the composition composed of Compound 1. Component Z of Compound 1 is Group Z-4

[0131] In an embodiment, the electronic device includes the composition composed of Compound 1. Component Z of Compound 1 is Group Z-5.

[0132] In an embodiment, the electronic device includes the composition composed of Compound 1. Component Z of Compound 1 is Group Z-6.

[0133] In an embodiment, the electronic device includes the composition composed of Compound 1. Component Z of Compound 1 is Group Z-7.

[0134] In an embodiment, the electronic device includes the composition composed two or more Compound 1s, the plurality of Compound 1s having two or more different Z components selected from Group Z-1, Group Z-2, Group Z-3, Group Z-4, Group Z-5, Group Z-6, and Group Z-7 and any combination thereof.

[0135] In an embodiment, the electronic device is an organic light-emitting diode (OLED) device. The present composition can be present in one, some, or all of the following layers: hole injection layer (HIL), a hole transport layer (HTL), an emitting material layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL). As a layer, the present composition has a layer thickness from 5 nanometers (nm), or 10 nm, or 20 nm, or 25 nm to 30 nm, or 35 nm, or 40 nm, or 50 nm, or 60 nm, or 70 nm, or 80 nm, or 90 nm.

[0136] In an embodiment, the electronic device is an OLED device and the present composition is present in the hole transport layer (HTL) and the HTL has a thickness from 5 nanometers (nm), or 10 nm, or 20 nm, or 25 nm to 30 nm, or 35 nm, or 40 nm, or 50 nm, or 60 nm, or 70 nm, or 80 nm, or 90 nm.

[0137] The present electronic device may comprise a combination of two or more embodiments disclosed herein.

[0138] Some embodiments of the present disclosure will now be described in detail in the following Examples.

Examples

1. Reagents and Test Methods

[0139] All solvents and reagents are obtained from commercial vendors, including Sigma-Aldrich, TCI, and Alfa Aesar, and are used in the highest available purities, and/or when necessary, recrystallized before use. Dry solvents are obtained from in-house purification/dispensing system (hexane, toluene, and tetrahydrofuran), or purchased from Sigma-Aldrich. All experiments involving “water sensitive compounds” are conducted in “oven dried” glassware, under nitrogen atmosphere, or in a glovebox. Reactions are monitored by analytical, thin-layer chromatography (TLC) on precoated glass plates (VWR 60 F254), and visualized by UV light and/or potassium permanganate staining. Flash chromatography is performed on an ISCO COMBIFLASH system with GRACERESOLV cartridges. GC-mass spectrometry (GC-MS) is performed on a HP 6890 series GC system with a “12 m×0.2 mm×0.55 μM” DB-MS column (coiled).

[0140] .sup.1H-NMR-spectra (500 MHz or 400 MHz) are obtained on a Varian VNMRS-500 or a VNMRS-400 spectrometer, at 30° C., unless otherwise noted. The chemical shifts are referenced to TMS (δ=0.00) in CDCl.sub.3.

[0141] .sup.13C-NMR spectra (125 MHz or 100 MHz) are obtained on a Varian VNMRS-500 or a VNRMS-400 spectrometer, and referenced to TMS (δ=0.00) in CDCl.sub.3.

[0142] Routine LC/MS studies are carried out as follows. Five microliter aliquots of the sample, as “3 mg/ml solution in THF,” are injected on an AGILENT 1200SL binary gradient, liquid chromatography, coupled to an AGILENT 6520 QTof, quadruple-time of flight MS system, via a dual spray electrospray (ESI) interface, operating in the PI mode. The following analysis conditions are used: column: 150×4.6 mm ID, 3.5 μm ZORBAX SB-C8; column temperature: 40° C.; mobile phase: 75/25 A/B to 15/85 A/B at 40 minutes; solvent A=0.1 v % formic acid in water; solvent B=THF; flow 1.0 mL/min; UV detection: diode array 210 to 600 nm (extracted wavelength 250,280 nm); ESI conditions: gas temperature 365° C.; gas flow—8 ml/min; capillary—3.5 kV; nebulizer—40 PSI; fragmentor—145V.

[0143] DSC is performed using a 2000 instrument at a scan rate of 10° C./min, and in a nitrogen atmosphere for all cycles. The sample (about 7-10 mg) is scanned from room temperature to 300° C., cooled to −60° C., and reheated to 300° C. The glass transition temperature (T.sub.g) is measured on the second heating scan. Data analysis is performed using TA Universal Analysis software. The T.sub.g is calculated using the “mid-point of inflection” methodology.

2. Modeling

[0144] All computations utilize the Gaussian09 program.sup.1. The calculations are performed with the hybrid density functional theory (DFT) method, B3LYP,.sup.2 and the 6-31G* (5d) basis set..sup.3 The singlet state calculations use the closed shell approximation, and the triplet state calculations use the open shell approximation. The HOMO and LUMO values are determined from the orbital energies of the optimized geometry of the singlet ground state, and this energy is denoted as E.sub.50(S.sub.0). The Triplet Energy (T.sub.1) is the difference between the total energy of the optimized triplet state and the optimized singlet state. .sup.1.Gaussian 09, Revision A.02, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; lshida, M.; Nakajima, T.; Honda, Y.; Kite, O.; Nakai, N.; Vreven, T.; Montgomery, Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J., Gaussian, Inc., Wallingford Conn., 2009..sup.2.(a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev 8 1988, 37, 785. (c) Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.

[0145] .sup.3.(a) Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724. (b) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257. (c) Gordon, M. S. Chem. Phys. Lett. 1980, 76, 163.

[0146] The estimation of h-mobility (λ+) is performed by a stepwise process. First, the geometry of the HTL molecule is optimized in the radical cation state E.sub.cat(Cat). In the next step, the energy of the radical cation is obtained in the singlet ground state geometry, E.sub.cat(S.sub.0). In the third step, the energy of singlet state is obtained in the radical cation geometry, E.sub.50(Cat). The h-mobility (λ+) is estimated using the following equation;

λ+=(E.sub.cat(S.sub.0)−E.sub.cat(Cat))+(E.sub.50(Cat)−E.sub.50(S.sub.0))

[0147] All values are quoted in electronvolts (eV).

[0148] HOMO, LUMO, Triplet, and H-mobility values are calculated by B3LYP/6-31G* method and are shown in Table 1 below.

TABLE-US-00001 TABLE 1 h-mo- HOMO LUMO T.sub.1 bility Component Z (eV) (eV) (eV) (λ + eV) MW Structure (i) (Z-1) −4.73 −0.92 2.64 0.18 690.87 Structure (ii) (Z-2) −4.70 −0.77 2.66 0.18 738.93 Structure (iii) (Z-3) −4.76 −0.96 2.67 0.22 694.95 Structure (Z-4) −4.76 −1.00 2.45 0.19 704.92 Structure (Z-5) −4.70 −0.90 2.65 0.18 704.92 Structure (Z-6) −4.78 −0.96 2.69 0.20 718.33 Structure (Z-7) −4.76 −0.94 2.69 0.20 732.97

3. Synthesis

[0149] A. Synthesis of HTL with Structure (i)

##STR00023##

[0150] A 3 necked 500 mL round bottomed flask, equipped with a stir bar, a thermocouple, and a water condenser, and with nitrogen inlet, is charged with phenyl carbazole boronic acid 1 (9.5 g, 33.06 mmol), 1-iodo-4-bromobenzene (9.37 g, 33.12 mmol), palladium acetate (0.139 g, 0.62 mmol), triphenyl phosphine (0.449 g, 1.71 mmol), and toluene 140 mL). Then 44 g of “40% (w/w) potassium phosphate tribasic diluted with water (46 mL) and ethanol (46 mL)” is added, and the reaction heated to 75° C. (reflux). After 2 hours (h), the reaction is allowed to cool to room temperature, and the mixture is extracted with ethyl acetate. The combined organic layers are dried over magnesium sulfate, filtered, and concentrated. The crude material is purified on the combiflash (hexane/5% ethyl acetate) to give approximately 9 g of product. The material is dissolved in toluene (30 mL), and is precipitated with hexanes (90 mL) (solids started to form after 60 mL added). The precipitate is isolated by vacuum filtration, to give pure product 3 (8.3 g, 20.8 mmol, 63%).

[0151] .sup.1H NMR (400 MHz, Chloroform-d) δ 8.30 (dd, J=1.8, 0.7 Hz, 1H), 8.18 (dt, J=7.8, 1.0 Hz, 1H), 7.65-7.54 (m, 9H), 7.51-7.39 (m, 4H), 7.31 (ddd, J=8.0, 5.2, 3.0 Hz, 1H).

[0152] .sup.13C NMR (101 MHz, CDCl.sub.3) δ 141.42, 140.94, 140.54, 137.56, 132.16, 131.83, 129.95, 128.88, 127.62, 127.08, 126.28, 125.16, 123.95, 123.34, 120.71, 120.37, 120.17, 118.64, 110.15, 109.99.

##STR00024##

[0153] A 250 mL three necked round bottomed flask equipped with a stir bar, thermocouple, heating mantle, and water condenser, and with nitrogen inlet is charged with 3-(4-bromophenyl)-N-phenylcarbazole 3 (4.46 g, 11.2 mmol), 4-aminobiphenyl (2.11 g, 12.5 mmol), sodium t-butoxide (2.18 g, 22.7 mmol) and palladium acetate (0.053 g, 0.24 mmol) and the flask is purged with nitrogen for 5 minutes. Toluene (67 mL) that has been degassed with nitrogen for 5 minutes is added followed by tri-tert-butylphosphine (0.120 g, 0.6 mmol) dissolved in toluene (3 mL) and the reaction heated to 110° C. (start time: 5 PM). After 16.5 hours (h), HPLC showed very little conversion to product so more sodium t-butoxide (1.0 g) is added followed by Pd(dppf)Cl.sub.2 chloroform adduct (0.20 g). After 39 h the reaction is cooled to room temperature and partitioned between water and ethyl acetate. The aqueous layer is extracted with ethyl acetate and the combined organic layers are dried over magnesium sulfate, filtered, and concentrated. The crude material is dissolved in methylene chloride and concentrated onto ˜40 g of silica gel and purified on the combiflash (0 to 30% methylene chloride/hexanes). Fractions 36-60 are collected to provide the titled compound (5) in 97% purity (3.22 g, 6.62 mmol, 59%).

[0154] .sup.1H NMR (400 MHz, Chloroform-d) δ 8.32 (dd, J=1.8, 0.7 Hz, 1H), 8.18 (dt, J=7.7, 1.0 Hz, 1H), 7.69-7.50 (m, 11H), 7.50-7.37 (m, 6H), 7.36-7.26 (m, 2H), 7.25-7.14 (m, 4H), 5.82 (s, 1H).

[0155] .sup.13C NMR (101 MHz, CDCl.sub.3) δ 141.35, 137.74, 129.91, 128.75, 127.47, 127.09, 126.61, 126.09, 123.53, 120.36, 120.02, 109.92.

##STR00025##

[0156] Phenanthrenequinone (5.77 g; 27.7 mmol) is dissolved in 80 mL of methanesulfonic acid in a 250 mL round-bottomed flask. N-bromosuccinimide (NBS) (4.93 g; 27.7 mmol) is added slowly in small portions over a period of 30 min. The solution is stirred at room temperature overnight. It is then poured into a mixture of ice and water to terminate this reaction and an orange precipitate forms. The orange precipitate is dissolved in CH.sub.2Cl.sub.2 and then washed with an aqueous solution of saturated sodium bicarbonate. The solvent is removed under reduced pressure, and the product is purified by column chromatography (50-70% methylene chloride/hexane gradient) to afford Compound 7 (Yield is 44.0%).

##STR00026##

[0157] Compound 7 (8 g) is suspended in THF (250 mL) and MeMgCl (37.2 mL of a 3 M in THF) is added. The mixture is stirred overnight at 50° C. and glacial acetic acid (20 mL) is added under ice cooling and the solution is diluted with EtOAc. After washing twice with saturated NaCl solution, the solution is dried over Na.sub.2SO.sub.4 and solvent is removed under vacuum (Yield is 90.0%).

##STR00027##

[0158] Compound 8 (8 g, 25.04 mmole) is dissolved in glacial acetic acid (400 mL) and the mixture is heated at 130° C. for 30 min. To the mixture, Zn (8.08 g) is added slowly, which is followed by the slow addition of HCl (12 M, 8 mL). After 30 minutes another addition of Zn (8 g) is added along with HCl (12 M, 8 mL). The mixture is refluxed for 12 h and upon cooling to room temp and the addition of water (500 mL) a solid is formed. The solid is isolated upon filteration and it is washed with a NaOH solution and is purified by column chromatography (100% hexane) (Yield is 64.9%).

[0159] .sup.1H NMR (400 MHz, chloroform-d) δ ppm 2.67 (s, 3H) 2.71 (s, 3H) 7.56-7.68 (m, 3H) 8.09 (d, J=7.63 Hz, 1H) 8.22 (s, 1H) 8.53 (d, J=8.80 Hz, 1H) 8.62 (d, J=7.82 Hz, 1H)

##STR00028##

[0160] The reaction is undertaken in a nitrogen dry box. A 100 mL round bottomed flask is charged with 5 (1.2 g, 2.46 mmol), 9 (0.70 g, 2.46 mmol), NaOtBu (0.355 g, 3.7 mmol), Pd(dppf)Cl.sub.2 (0.040 g, 0.049 mmol), and toluene (50 mL). The mixture is stirred at 110° C. overnight. An aliquot is removed and analysis by GC-MS and NMR spectroscopy shows that the reaction is complete. The reaction is allowed to cool and is treated with EtOAc (200 mL) and water (200 mL). The organic layer is isolated, dried with MgSO.sub.4, and is filtered. The solvent is removed under reduced pressure to afford crude structure (i). It is purified by column chromatography using the Biotage with a mixed solvent of CH.sub.2Cl.sub.2 and hexane. The solvent profile is increased to 25% CH.sub.2Cl.sub.2 over 6 column lengths and this ratio is until structure (i) elutes. Yield is 1.2 g (70%).

[0161] .sup.1H NMR (400 MHz, C.sub.6D.sub.6) δ 8.55 (d, J=9.0 Hz, 1H), 8.54-8.50 (m, 1H), 8.44 (d, J=1.7 Hz, 1H), 8.20 (d, J=2.3 Hz, 1H), 8.12 (d, J=6.9 Hz, 1H), 7.99-7.91 (m, 1H), 7.68 (d, J=8.6 Hz, 3H), 7.59 (dd, J=8.9, 2.3 Hz, 1H), 7.56-7.50 (m, 4H), 7.45 (d, J=6.5 Hz, 7H), 7.38-7.18 (m, 10H), 7.08 (d, J=7.2 Hz, 1H), 2.37 (s, 3H), 2.28 (s, 3H).

[0162] .sup.13C NMR (101 MHz, C.sub.6D6) δ 147.94, 147.09, 146.70, 141.93, 141.17, 140.80, 138.15, 137.53, 136.05, 134.24, 133.59, 132.32, 130.28, 130.12, 130.02, 129.23, 129.14, 128.79, 128.46, 128.30, 128.18, 128.17, 127.45, 127.36, 127.16, 127.11, 126.53, 126.53, 126.31, 126.21, 125.97, 125.69, 125.40, 125.07, 124.83, 124.68, 124.56, 124.20, 123.58, 123.03, 120.86, 120.57, 119.51, 119.01, 110.49, 110.31, 15.91, 15.89.

[0163] B. Synthesis for HTL with Structure (ii)

##STR00029##

[0164] The anthranilic acid (3.62 g; 16.9 mmol) is added to a 500 mL round-bottomed flask and MeCN (400 mL) is added. The mixture is heated to 50° C. and rapidly stirred. This slurry is added drop wise to a solution of anthracene (6.0 g; 33.7 mmol) in MeCN (300 mL) that is heated to just below its reflux. Concurrently, a solution of the BuONO (4.9 mL) in MeCN (400 mL) is also added. The addition is carried out over 3 hours. The reaction cooled to room temperature and ca. 90% of the solvent is removed on a roto yap. The mixture is filtered and 3.9 grams of anthracene is isolated. The mother liquor is analyzed and shown to contain 2-bromotriptycene. It is treated with CH.sub.2Cl.sub.2 (200 mL) and water (200 mL). The organic layer is isolated, dried with MgSO.sub.4, and filtered. 3.3 g of a sticky yellow brown solid is obtained upon removing the solvent. It is purified by column chromatography (0-20% CH.sub.2Cl.sub.2 in hexane) and Compound 10 (0.9 g; 16% yield) is obtained as a colorless solid. .sup.1H NMR (400 MHz, Chloroform-d) δ 7.52 (d, J=1.9 Hz, 1H), 7.37 (dd, J=5.4, 3.2 Hz, 4H), 7.29-7.19 (m, 2H), 7.11 (dd, J=7.8, 1.9 Hz, 1H), 7.00 (d, J=8.5 Hz, 4H), 5.38 (d, J=5.9 Hz, 2H); .sup.13C NMR (101 MHz, Chloroform-d) δ 147.75, 144.91, 144.64, 144.62, 128.05, 127.02, 125.57, 125.53, 125.20, 123.91, 123.83 118.66, 53.84, 53.67.

##STR00030##

[0165] The reaction is undertaken in a nitrogen dry box. A 100 mL round bottomed flask is charged with Compound 5 (1.45 g, 2.97 mmol), Compound 10 (0.899 g, 2.70 mmol), NaOtBu (0.390 g, 4.06 mmol), Pd(dppf)Cl.sub.2 (0.044 g, 0.054 mmol), and toluene (100 mL). The mixture is stirred at 110° C. overnight. An aliquot is removed and analysis by GC-MS and NMR spectroscopy shows that the reaction is complete. The reaction is allowed to cool and is treated with EtOAc (200 mL) and water (200 mL). The organic layer is isolated, dried with MgSO.sub.4, and is filtered. The solvent is removed under reduced pressure to afford crude HTL-2. It is purified by column chromatography using the Biotage with a mixed solvent of CH.sub.2Cl.sub.2 and hexane. The solvent profile is increased to 40% CH.sub.2Cl.sub.2 over 6 column lengths and this ratio is used until HTL-2 eluted. Yield is 1.5 g (75.2%).

[0166] .sup.1H NMR (400 MHz, Chloroform-d) δ 8.32 (d, J=1.7 Hz, 1H), 8.21-8.14 (m, 1H), 7.66-7.54 (m, 9H), 7.50-7.37 (m, 9H), 7.41-7.24 (m, 6H), 7.25 (d, J=3.0 Hz, 3H), 7.19-7.09 (m, 4H), 7.06-6.98 (m, 4H), 6.81 (dd, J=7.9, 2.2 Hz, 1H), 5.40 (s, 1H), 5.33 (s, 1H);

[0167] .sup.13C NMR (101 MHz, CDCl.sub.3) δ 147.30, 146.47, 145.55, 145.24, 144.77, 140.68, 140.07, 137.70, 136.26, 132.98, 129.90, 128.73, 127.91, 127.70, 127.47, 127.06, 126.75, 126.63, 126.08, 125.21, 125.14, 125.07, 124.63, 124.22, 123.87, 123.71, 123.49, 121.08, 120.35, 120.03, 118.31, 110.00, 109.91, 54.08, 53.55.

[0168] C. Synthesis for Structure (iii)

##STR00031##

[0169] In a 500 mL round bottomed flask, compound 11 (25 g, 147.7 mmoles) and ammonium bromide (15.9 g, 162.5 mmol) are dissolved in glacial acetic acid (300 mL). Using a syringe pump, a 30% solution of H.sub.2O.sub.2 (18.1 mL) is added over 2 h. The mixture is allowed to stir overnight and is then quenched by carefully adding a saturated solution of Na.sub.2CO.sub.3 and the mixture is extracted with methylene chloride (1 L). The organic layer is dried with MgSO.sub.4 and filtered. The crude mixture is purified by chromatography over silica gel using hexane/methylene chloride (4:1) to afford 12 as a colorless solid (65% yield 23.8 g).

[0170] .sup.1H NMR (400 MHz, CDCl.sub.3) δ: 7.49-7.39 (m, 4H), 7.39-7.33 (m, 1H), 7.28-7.18 (m, 1H), 6.73-6.54 (m, 1H), 3.75 (s, 2H).

[0171] .sup.13C NMR (101 MHz, CDCl.sub.3) δ: 142.62, 138.15, 132.76, 131.04, 129.38, 128.95, 128.89, 127.66, 117.03, 110.15.

##STR00032##

[0172] Compound 12 is added to a stirred solution of 12 M HCl (1.7 mL) and water (25 mL) in a 50 mL round bottom flask. The flask is cooled to 0° C. on an ice bath and a solution of NaNO.sub.2 [1.23 g dissolved in water (5 mL)] is added dropwise over 5 min. The slurry is stirred for 30 min and then added to a cooled (0° C.) solution of KI (20 mL of water). After the initial vigorous reaction the solution is heated to 50° C. The mixture is extracted with CH.sub.2Cl.sub.2 and purified by column chromatography to afford 13 as a colorless solid.

##STR00033##

[0173] A solution of Compound 13 (3 g) in THF (60 mL) is cooled to −78° C. and n-BuLi is added drop-wise under an atmosphere of nitrogen. After 15 minutes dimethylchlorosilane is added drop-wise at −78° C. and the mixture is warmed to 25° C. slowly. After stirring overnight, a saturated solution of NH.sub.4Cl in water is added and the mixture extracted with diethyl ether (360 mL). The organic layer is dried over anhydrous MgSO.sub.4, filtered, and concentrated under reduced pressure. The product is isolated by column chromatography on silica gel (hexane eluent using Biotage). Fractions 11 through 21 are combined and concentrated on a rotary evaporator (1 g, 41%). The clear oil is transferred into a tared vial and then moved to a nitrogen atmosphere glove box.

##STR00034##

[0174] Compound 14 (3.86 g, 13.3 mmol) is dissolved in THF (100 mL). n-BuLi (10.0 mL, 1.6 M, 15.9 mmol) is added drop-wise and the reaction is warmed to 0° C. over 1 h. Trimethylsilylchloride (3.37 mL, 26.5 mmol) is then added and the reaction is stirred overnight. The reaction is poured into water and extracted with Et.sub.2O. The organic layer is further washed with water and brine. The aqueous layers are extracted one additional time with Et.sub.2O. The combined organics are dried over MgSO.sub.4 and then concentrated under high vacuum. The resulting oil is purified by column chromatography using a 100 g SNAP column on the Biotage eluting with hexane. Upon concentration of these fractions the product is obtained as a colorless oil (2.87 g, 76%).

[0175] .sup.1HNMR (400 MHz, CDCl.sub.3) δ 7.62 (dd, J=7.3, 0.7 Hz, 1H), 7.52 (dd, J=7.3, 1.2 Hz, 1H), 7.46-7.31 (m, 7H), 4.32 (p, J=3.8 Hz, 1H), 0.28 (s, 9H), 0.06 (d, J=3.8 Hz, 6H).

[0176] .sup.13C NMR (101 MHz, CDCl.sub.3) δ 148.53, 144.16, 141.82, 136.63, 134.48, 134.14, 131.44, 129.43, 128.03, 127.23, −1.02, −2.89.

##STR00035##

[0177] Compound 15 (2.87 g, 10.1 mmol) is added to a vial and diluted in dioxane (30 mL). RhCl(PPh.sub.3).sub.3 (0.047 g, 0.051 mmol) is then added and the vial is transferred out of the box and placed in a pre-heated metal block at 135° C. After 3 h the reaction is analyzed by GC/MS showing 80% conversion. An additional equivalent of RhCl(PPh.sub.3).sub.3 (0.047 g, 0.051 mmol) is added and heating is continued for 2 h upon which complete conversion is obtained. The solvent is removed and the crude residue is purified by column chromatography on silica gel eluting with hexane (1.96 g, 69%).

[0178] .sup.1HNMR (400 MHz, CDCl.sub.3) δ 7.99 (d, J=1.0 Hz, 1H), 7.89 (dt, J=7.8, 0.9 Hz, 1H), 7.65-7.60 (m, 2H), 7.47-7.40 (m, 2H), 7.30-7.25 (m, 1H), 0.42 (s, 6H), 0.32 (s, 9H).

[0179] .sup.13C NMR (101 MHz, CDCl.sub.3) δ: 149.01, 147.92, 143.59, 140.68, 140.01, 133.80, 133.41, 133.10, 131.17, 128.37, 126.41, 121.81, 0.00, −2.19.

##STR00036##

[0180] Compound 16 (1.96 g, 6.89 mmol) is dissolved in dichloromethane and cooled to −25° C., a solution of iodine monochloride (1.0 M in CH.sub.2Cl.sub.2, 6.9 mL) and the solution is stirred and warmed to room temperature over 1 h. An additional 0.69 mL of iodine monochloride solution is added and stirred for another 30 minutes when another 0.07 mL is added. The reaction is stirred for another 10 minutes and then is quenched with sodium thiosulfate (10% aqueous, 30 mL) and the reaction is stirred for 30 minutes. The organic layer is collected the aqueous layer is extracted with dichloromethane (2×20 mL). The combined organic fractions are rinsed further with water (2×40 mL), brine (40 mL), and dried with MgSO.sub.4. The solution is filtered and concentrated. The resulting oil is then purified by column chromatography eluting with hexane. Upon concentration the desired product is isolated as a colorless oil (1.5 g, 65%).

[0181] .sup.1H NMR (400 MHz, CDCl.sub.3) δ: 8.16 (d, J=1.4 Hz, 1H), 7.76 (dt, J=7.8, 0.9 Hz, 1H), 7.66-7.57 (m, 2H), 7.43 (td, J=7.6, 1.4 Hz, 1H), 7.35 (d, J=7.5 Hz, 1H), 7.30 (td, J=7.3, 1.0 Hz, 1H), 0.41 (s, 6H).

[0182] .sup.13C NMR (101 MHz, CDCl.sub.3) δ: 149.92, 146.38, 138.97, 138.16, 136.05, 134.10, 132.79, 130.31, 130.13, 127.95, 121.03, 97.41, −3.40.

##STR00037##

[0183] In a large flask is placed Compound 5 (1.0 g, 2.05 mmol) and 17 (0.69 g, 2.05 mmol), sodium t-butoxide (0.296 g, 3.08 mmol), and Pd(dppf).CHCl.sub.3 (35 mg, 0.041 mmol). The reaction is diluted with toluene (10 mL) and the reaction is heated to 100° C. overnight. The reaction is then cooled and placed in a separatory funnel and the organic fraction is washed with water (2×100 mL). The water layer is again extracted with Et.sub.2O (2×100 mL) and the combined organics are rinsed with brine (100 mL) and dried over Na.sub.2SO.sub.4. After filtration the volatiles are removed on a rotary evaporator. Residue is concentrated onto silica gel and chromatographed using a hexanes/dichloromethane gradient from 0 to 30% dichloromethane. The combined fractions are collected and dried to yield the product as a fluffy white solid. This reaction is repeated with the Compound 5 (1.45 g, 2.97 mmol), Compound 17 (1.0 g, 2.97 mmol), sodium t-butoxide (0.429 g, 4.46 mmol), and Pd(dppf).CHCl.sub.3 (51 mg, 0.060 mmol) and toluene (20 mL). The purified material from the two reactions is combined to give 1.2 g (34% yield) of the desired product in 98% purity. Successive precipitation of this material from dichloromethane and acetonitrile yielded 0.996 g of the product in 99.8% purity.

[0184] .sup.1H NMR (400 MHz, CDCl.sub.3d) δ 8.36 (dd, J=1.8, 0.6 Hz, 1H), 8.19 (dt, J=7.8, 1.0 Hz, 1H), 7.70-7.57 (m, 10H), 7.54 (dd, J=8.3, 2.1 Hz, 3H), 7.53-7.43 (m, 3H), 7.47-7.38 (m, 3H), 7.39-7.20 (m, 10H), 7.08 (dd, J=7.8, 2.0 Hz, 1H), 0.45 (s, 6H).

[0185] .sup.13C NMR (101 MHz, CDCl.sub.3) δ 149.80, 149.37, 147.44, 146.99, 146.18, 141.36, 140.66, 140.22, 139.70, 137.71, 136.78, 135.45, 133.61, 132.95, 132.64, 132.33, 130.00, 129.91, 128.76, 128.08, 127.87, 127.49, 127.44, 127.07, 126.86, 126.70, 126.10, 125.18, 125.04, 124.38, 123.92, 123.50, 123.13, 120.97, 120.35, 120.05, 118.39, 116.40, 110.03, 109.92, −2.97.

4. OLED Device Fabrication and Testing

[0186] A. OLED Device

[0187] All organic materials are purified by sublimation before deposition. OLEDs are fabricated onto an ITO coated glass substrate that served as the anode, and topped with an aluminum cathode. All organic layers are thermally deposited by chemical vapor deposition, in a vacuum chamber with a base pressure of <10.sup.−7 torr. The deposition rates of organic layers are maintained at 0.1.sup.˜0.05 nm/s. The aluminum cathode is deposited at 0.5 nm/s. The active area of the OLED device is “3 mm×3 mm,” as defined by the shadow mask for cathode deposition.

[0188] Each cell, containing HIL, HTL, EML host, EML dopant, ETL, or EIL, is placed inside a vacuum chamber, until it reaches 10.sup.−6 torr. To evaporate each material, a controlled current is applied to the cell, containing the material, to raise the temperature of the cell. An adequate temperature is applied to keep the evaporation rate of the materials constant throughout the evaporation process.

[0189] For the HIL layer, N1,N1′-([1,1′-biphenyl]-4,4′-diyl)bis(N1-(naphthalen-1-yl)-N4,N4-diphenylbenzene-1,4-diamine) is evaporated at a constant 1 A/s rate, until the thickness of the layer reaches 600 Angstrom. Simultaneously, the HTL compounds are evaporated at a constant 1 A/s rate, until the thickness reaches 200 Angstrom. The N4,N4′-di(naphthalen-1-yl)-N4,N4′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (NPB) is used as a reference material to compare with the present compositions. Other nonlimiting examples of HTL compounds include di(p-tolyl)aminophenyl]cyclohexane (TPAC), N,N-diphenyl-N,N-bis(3-methylphenyl)-1,1-biphenyl-4,4-diamine (TPD).

[0190] For the EML layer, 9,10-di(naphthalen-2-yl)anthracene (ADN, host) and (E)-4,4′-(ethene-1,2-diyl)bis-(N,N-diphenylaniline)(DPAVB, dopant) are co-evaporated, until the thickness reaches 350 Angstrom. The deposition rate for host material is 0.98 A/s, and the deposition for the dopant material is 0.02 A/s, resulting in a 2% doping of the host material. For the ETL layer, tris(8-hydroxyquinolinato)aluminum (Alq3) is evaporated at a constant 1 A/s rate, until the thickness reaches 300 Angstrom. Finally, “20 Angstrom” of a thin electron injection layer (Liq) is evaporated at a 0.2 A/s rate. See Table 2.

[0191] The current-voltage-brightness (J-V-L) characterizations for the OLED devices are performed with a source measurement unit (KEITHLY 238) and a luminescence meter (MINOLTA CS-100 A). Electroluminescence (EL) spectra of the OLED devices are collected by a calibrated CCD spectrograph.

TABLE-US-00002 TABLE 2 OLED Device Materials Commer- cial Name Name Hole Injection N1,N1′-([1,1′-biphenyl]-4,4′-diyl)bis(N1- Material (naphthalen-1-yl)-N4,N4-diphenylbenzene-1,4- diamine) Hole Transporting N4,N4′-di(naphtalen-1-yl)-N4,N4′-diphenyl-[1,1′- NPB* Material Or HTL-1 biphenyl]-4,4′-diamine (Example 1) Fl Blue Host 9,10-di(naphthalen-2-yl)anthracene ADN Fl Blue Dopant (E)-4,4′-(ethane-1,2-diyl)bis(N,N-diphenylaniline) DPAVB Electron Transporting tris(8-hydroxyquinolinato)aluminum Alq3 Material Electron Injection lithium quinolate Liq Material *comparative

[0192] B. OLED Device with Present Compositions

[0193] The present compositions are each further purified by sublimation, and incorporated into OLED devices for preliminary evaluation against the reference NPB.

[0194] OLED devices are fabricated, as discussed above, on coated glass substrates with multiple organic layers sandwiched between a transparent ITO anode and an aluminum cathode. OLED devices are produced as described above replacing the HTL layer (NBP, reference) with Example 1, HTL-1 (Structure (i)).

TABLE-US-00003 TABLE 3 OLED Device Data Voltage Luminous Efficiency CIE.sup.3 @1000 nit.sup.1 [V] @1000 nit [Cd/A].sup.2 (X, Y) NPB* 6.6 4.0 148, 150 Example 1 6.4 4.8 148, 152 HTL-1 with Structure (i) *comparative .sup.1Nit = candela per square meter (Cd/m.sup.2) .sup.2Cd/A = candelas per ampere (Amp) .sup.3CIE = The International Commission on Illumination

[0195] Table 3 shows the OLED device testing results of Example 1 compared to reference compound, NPB in the HTL.

[0196] As seen in Table 3, the device using Example 1, HTL-1 (Structure (i)), exhibits better (higher) efficiency when compared to the device containing the reference compound, NPB, for the HTL layer.

[0197] It is specifically intended that the present disclosure not be limited to the embodiments and illustrations contained herein, but include modified forms of those embodiments including portions of the embodiments and combinations of elements of different embodiments as come within the scope of the following claims.