COMPOUND AND ORGANIC ELECTRONIC DEVICE COMPRISING THE SAME

Abstract

Provided are a novel compound and an organic electronic device using the same. The novel compound is represented by the following Formula (I):

##STR00001##

G.sup.1 and G.sup.2 in Formula (I) are each independently selected from the group consisting of:

##STR00002##

and G.sup.11 and G.sup.12 are each a specific aryl group or heteroaryl group. The organic electronic device comprising the novel compound has the beneficial effects of improved luminous efficacy and external quantum efficiency.

Claims

1. A compound represented by the following Formula (I): ##STR00326## wherein, G.sup.1 and G.sup.2 in Formula (I) are each independently selected from the group consisting of: ##STR00327## G.sup.11 and G.sup.12 are each independently selected from the group consisting of: ##STR00328## R.sup.1 to R.sup.3 are each independently selected from the group consisting of: a deuterium atom, a halo group, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, and an alkynyl group having 2 to 6 carbon atoms; J is an integer from 1 to 2; k is an integer from 0 to 2; and n1 is an integer from 0 to 5, n2 is an integer from 0 to 4, and n3 is an integer from 0 to 7.

2. The compound as claimed in claim 1, wherein the compound is represented by the following Formulae (I-I) to (I-VI): ##STR00329## ##STR00330##

3. The compound as claimed in claim 1, wherein G.sup.11 and G.sup.12 are each independently selected from the group consisting of: ##STR00331## ##STR00332## ##STR00333## ##STR00334##

4. The compound as claimed in claim 1, wherein G.sup.1 and G.sup.2 are each independently selected from the group consisting of: ##STR00335## ##STR00336## ##STR00337## ##STR00338## ##STR00339## ##STR00340## ##STR00341## ##STR00342## ##STR00343## ##STR00344## ##STR00345## ##STR00346## ##STR00347## ##STR00348## ##STR00349## ##STR00350## ##STR00351## ##STR00352## ##STR00353## ##STR00354## ##STR00355## ##STR00356## ##STR00357## ##STR00358## ##STR00359## ##STR00360## ##STR00361## ##STR00362## ##STR00363## ##STR00364## ##STR00365## ##STR00366## ##STR00367## ##STR00368## ##STR00369## ##STR00370## ##STR00371## ##STR00372## ##STR00373## ##STR00374## ##STR00375## ##STR00376## ##STR00377## ##STR00378## ##STR00379## ##STR00380## ##STR00381## ##STR00382## ##STR00383## ##STR00384## ##STR00385## ##STR00386## ##STR00387## ##STR00388## ##STR00389## ##STR00390## ##STR00391## ##STR00392## ##STR00393## ##STR00394## ##STR00395## ##STR00396## ##STR00397## ##STR00398##

5. The compound as claimed in claim 1, wherein G.sup.1 and G.sup.2 are the same.

6. The compound as claimed in claim 1, wherein j is the integer 1 and k is the integer 0.

7. The compound as claimed in claim 1, wherein j is the integer 1 and k is the integer 1.

8. The compound as claimed in claim 1, wherein the compound is selected from the group consisting of: ##STR00399## ##STR00400## ##STR00401##

9. An organic electronic device, comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises the compound as claimed in claim 1.

10. The organic electronic device as claimed in claim 9, wherein the organic electronic device is an organic light emitting device.

11. The organic electronic device as claimed in claim 10, wherein the organic light emitting device comprises: a hole injection layer formed on the first electrode; a hole transport layer formed on the hole injection layer; an emission layer formed on the hole transport layer; an electron transport layer formed on the emission layer, wherein the organic layer is the electron transport layer; an electron injection layer formed between the electron transport layer and the second electrode.

12. The organic electronic device as claimed in claim 10, wherein the organic light emitting device comprises: a hole injection layer formed on the first electrode; a hole transport layer formed on the hole injection layer; an emission layer formed on the hole transport layer; a hole blocking layer formed on the emission layer, wherein the organic layer is the hole blocking layer; an electron transport layer formed on the hole blocking layer; an electron injection layer formed between the electron transport layer and the second electrode.

13. The organic electronic device as claimed in claim 9, wherein the organic layer comprises the compound as claimed in claim 3.

14. The organic electronic device as claimed in claim 9, wherein the organic layer comprises the compound as claimed in claim 4.

15. The organic electronic device as claimed in claim 9, wherein the compound is selected from the group consisting of: ##STR00402## ##STR00403## ##STR00404##

Description

BRIEF DESCRIPTION OF THE DRAWING

[0052] FIG. 1 illustrates a schematic cross-sectional view of an OLED.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0053] Hereinafter, one person skilled in the arts can easily realize the advantages and effects of a novel compound and an organic light emitting device using the same in accordance with the present invention from the following examples. It should be understood that the descriptions proposed herein are just preferable examples only for the purpose of illustrations, not intended to limit the scope of the invention. Various modifications and variations could be made in order to practice or apply the present invention without departing from the spirit and scope of the invention.

Preparation of Intermediate A

[0054] Intermediate A, which was used to synthesize the novel compounds, could be purchased or synthesized by the following Scheme I through steps A-1 to A-4.

##STR00238##

Step A-1: Synthesis of Intermediate A-1

[0055] A mixture of dibenzosuberone (86 g, 1.0 eq), N-bromosuccinimide (NBS, 106 g, 1.4 eq), and benzyl peroxide (0.7 g, 0.01 eq) in carbon tetrachloride (CCl.sub.4, 430 ml) was heated to 85 C. The reaction was monitored by HPLC. After completion of the reaction, the precipitate was separated by filtration and washed with MeOH, then purified by recrystallization. The purified product was concentrated to dryness, whereby a white solid product was obtained in an amount of 144 g and a yield of 92.3%.

[0056] The purified product was identified as Intermediate A-1 by a field desorption mass spectroscopy (FD-MS) analysis. FD-MS analysis C.sub.15H.sub.10Br.sub.2O: theoretical value of 366.05 and observed value of 366.05.

Step A-2: Synthesis of Intermediate A-2

[0057] The obtained Intermediate A-1 (96.0 g, 1.0 eq) was dissolved in 960 ml of furan/tetrahydrofuran(THF) (v/v=2/1), and the reaction was cooled to 0 C. and then treated with KO-t-Bu (87.8 g, 3.0 eq). The reaction was allowed to stir for 1 hour (h) at 0 C. prior to raise up to room temperature (rt) and stirred for additional 12 h. After completion of the reaction, the solution was quenched by DI water and the organic layer was recovered by solvent extraction and dried over sodium sulfate. The solvent was removed from the organic layer by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography. The purified product was concentrated to dryness, whereby a light yellow solid product was obtained in an amount of 46.8 g in a yield of 51.1%.

[0058] The light yellow solid product was identified as Intermediate A-2 by FD-MS analysis. FD-MS analysis: C.sub.19H.sub.12O.sub.2: theoretical value of 272.3 and observed value of 272.3.

Step A-3: Synthesis of Intermediate A-3

[0059] A suspension of the obtained Intermediate A-2 (41.5 g, 1.0 eq) and 5% Pd/C (8.1 g, 0.025 eq) in 535 ml ethyl acetate (EA) was stirred for 3 h to 6 h under a hydrogen atmosphere provided by a balloon of hydrogen. The resulting mixture was filtered through a pad of celite and washed with EA, and the filtrate was concentrated under reduced pressure to obtain 41.8 g (100%) of Intermediate A-3 as a yellow solid. The obtained compound, Intermediate A-3, was directly used in the subsequent reaction without further purification.

Step A-4: Synthesis of Intermediate A

[0060] The obtained Intermediate A-3(41 g, 1.0 eq) and p-toluenesulfonic acid (PTSA, 55 g, 2.0 eq) in 530 ml of toluene was heated to reflux for 12 h. The reaction mixture was cooled to rt and then quenched with a saturated aqueous solution of NaHCO.sub.3 and extracted with CH.sub.2Cl.sub.2. The organic layer was washed with water, brine and dried with anhydrous Na.sub.2SO.sub.4 subsequently. Then the resulting solution was concentrated under reduced pressure and purified by column chromatography on silica gel with CH.sub.2Cl.sub.2/hexane (v/v=1/1) as eluent. 46.0 g of Intermediate A was obtained as light yellow solids in a yield of 91.5%.

[0061] The purified product was identified as Intermediate A by FD-MS analysis. FD-MS analysis C.sub.19H.sub.12O: theoretical value of 256.3 and observed value of 256.3.

Preparation of Intermediate Bn

[0062] Intermediate Bn, including Intermediates B1 to B4, which was used to synthesize the novel compounds, could be purchased or synthesized by the following Scheme II.

##STR00239##

[0063] The main difference of the preparation of Intermediates B1 to B4 was the material of Reactant An (Reactants A1 to A4) as listed in Table 1.

TABLE-US-00001 TABLE 1 the chemical structures, names, and CAS No. of Reactants Al to A4. Chemical Structure of Reactant An Reactant An Name CAS No. Reactant A1 [00240] 2-bromo-4-chlorobiphenyl 179526-95-5 Reactant A2 [00241] 2-bromo-3-chlorobiphenyl 154407-17-7 Reactant A3 [00242] 2,2-dibromobiphenyl 13029-09-9 Reactant A4 [00243] 2-bromo-5,3-dichlorobiphenyl

Synthesis of Reactant A4

[0064] A solution of 1-bromo-2-chloro-4-iodobenzene (1.0 eq), 4-chlorophenylboronic acid (1.1 eq), Pd(OAc).sub.2 (0.95 g, 0.01 eq), PPh.sub.3 (4.45 g, 0.04 eq), and 3.0 M K.sub.2CO.sub.3 aqueous solution (58.6 g, 2.0 eq in 144 ml H.sub.2O) in toluene (730 mL) was heated under nitrogen at 65 C. for 12 h. After cooling to room temperature, the solvent was then removed using a rotary evaporator, and the remaining substance was purified with column chromatography to obtain Reactant A4. The purified product was identified as Reactant A4 by FD-MS analysis. FD-MS analysis C.sub.8H.sub.7BrCl.sub.2: theoretical value of 301.99 and observed value of 301.99.

Synthesis of Intermediate B1

[0065] Take the Intermediate B1 as an example, it was synthesized by the above Scheme II through steps B-1 and B-2 as described below.

Step B-1: Synthesis of Spiro Alcohol

[0066] To the Reactant A1 (1.0 eq) in anhydrous THF (0.4 M), n-BuLi (1 eq) was added dropwise and stirred at 78 C. After stirring for 20 min, Intermediate A (0.7 eq) was added to the mixture and the reaction mixture was allowed to warm to room temperature. The reaction was monitored by HPLC. After completion of the reaction, the reaction solution was quenched with water, and a water layer was extracted with ethyl acetate. The extracted solution and an organic layer were combined and washed with saturated saline, and then dried with magnesium sulfate. After drying, this mixture was subjected to suction filtration, and then the filtrate was concentrated. 65 g of spiro alcohol was obtained as a light yellow, powdery solid and was directly used in step B-2 without further purification.

Step B-2: Synthesis of Intermediate B1

[0067] To the obtained spiro alcohol (1 eq), acetic acid (w/v=1/3 to the reactant) and H.sub.2SO.sub.4(5 drops) were added, and the mixture was stirred at 110 C. for 6 h. The reaction was monitored by HPLC. After completion of the reaction, the precipitate was separated by filtration. The remaining substance was purified with column chromatography to obtain 58 g of white solid in a yield of 93.0%.

[0068] The white solid product was identified as Intermediate B1 by FD-MS analysis. FD-MS analysis C.sub.31H.sub.19Cl: theoretical value 426.94, observed value 426.94.

Synthesis of Intermediates B2 to B4

[0069] The procedures for preparing the Intermediates B2 to B4 were similar to that for Intermediate B1, except for the material of Reactant An. The obtained intermediates B2 to B4 were present in white solids. The yields and MS analysis data of the intermediates B1 to B4 are also listed in the following Table 2.

TABLE-US-00002 TABLE 2 the material of Reactant An used to prepare Intermediate Bn, chemical structures of spiro alcohol and Intermediate Bn, and yields, formulae, and mass (M.sup.+) analyzed by FD-MS of Intermediate Bn. Material of Chemical Structure Yield Formula/ Reactant An of Spiro Alcohol Intermediate Bn (%) Mass(M.sup.+) [00244] [00245] [00246] 93.0 C.sub.31H.sub.19Cl/ 426.94 [00247] [00248] [00249] 89.1 C.sub.31H.sub.19Cl/ 426.94 [00250] [00251] [00252] 83.2 C.sub.31H.sub.19Br/ 471.39 [00253] [00254] [00255] 75.4 C.sub.31H.sub.18Cl.sub.2/ 461.38

Modifications of Intermediates Bn

[0070] In addition to the Intermediates B1 to B4, one person skilled in the art can adopt other Reactants An similar to Reactants A1 to A4 to react with Intermediate A to synthesize other desired Intermediates Bn through Scheme II. Applicable modifications of Intermediate Bn may be, for example, but are not limited to, Intermediates B5 to B7 as follows.

##STR00256##

Preparation of Intermediate Cn

[0071] Intermediate Cn, including Intermediates C1 to C4, could be purchased or synthesized by the following Scheme III.

##STR00257##

[0072] A mixture of Intermediate Bn (1.0 eq), bis(pinacolato)diboron (1.20 eq), tris(dibenzylideneacetone)dipalladium[Pd.sub.2(dba).sub.3] (0.015 eq), dicyclohexyl(2,6-dimethoxy-[1,1-biphenyl]-2-yl)phosphine (SPhos), and potassium acetate (KOAc) (3.0 eq) in anhydrous 1,4-dioxane (100 mL) was stirred at 110 C. for 8 h under nitrogen atmosphere. After cooling to room temperature, the solvent was then removed under reduced pressure, and the residue was purified with column chromatography to obtain a pale yellow solid product. The yield was listed in Table 3.

[0073] Each of the pale yellow solid products was identified as Intermediate Cn by a FD-MS analysis. The chemical structures, yield, formulae, and mass analyzed by FD-MS of Intermediate Cn were listed in Table 3.

TABLE-US-00003 TABLE 3 Intermediate Bn used for preparing Intermediate Cn, chemical structures, yields, formulae, and mass analyzed by FD-MS of Intermediate Cn Intermediate Cn Intermediate Bn Yield Formula/ Chemical Structure Chemical Structure (%) Mass (M.sup.+) [00258] [00259] 82 C.sub.37H.sub.31BO.sub.2/ 518.45 [00260] [00261] 85 C.sub.37H.sub.31BO.sub.2/ 518.45 [00262] [00263] 90 C.sub.37H.sub.31BO.sub.2/ 518.45

Modifications of Intermediates Cn

[0074] In addition to the Intermediates C1 to C3, one person skilled in the art can undergo a similar reaction of Scheme III to synthesize other desired Intermediates Cn, for example, but are not limited to, Intermediates C4 to C7. Said Intermediates C4 to C7 may be obtained from Intermediates B4 to B7 through a reaction of Scheme III, respectively.

Preparation of Reactants Bn

[0075] Reactants Bn, such as Reactants B1 to B20, applicable to prepare a novel compound were listed in Table 4. Most of Reactants B1 to B7, B9 to B18 and B20 were purchased from Sigma-Aldrich.

TABLE-US-00004 TABLE 4 chemical structures and the CAS No. of the Reactants B1 to B20 Reactant Reactant B1 Reactant B2 Reactant B3 Bn Chemical structure [00264] [00265] [00266] CAS No. 3842-55-5 1205748-61-3 1616231-57-2 Reactant Reactant B4 Reactant B5 Reactant B6 Bn Chemical structure [00267] [00268] [00269] CAS No. 29509-91-9 2142681-84-1 1618107-00-8 Reactant Reactant B7 Reactant B8 Reactant B9 Bn Chemical structure [00270] [00271] [00272] CAS No. 1300115-09-6 1588407-97-9 Reactant Reactant B10 Reactant B11 Reactant B12 Bn Chemical structure [00273] [00274] [00275] CAS No. 1421599-34-9 3114-52-1 774-53-8 Reactant Reactant B13 Reactant B14 Reactant B15 Bn Chemical structure [00276] [00277] [00278] CAS No. 307929-32-4 1472062-94-4 1883265-32-4 Reactant Reactant B16 Reactant B17 Reactant B18 Bn Chemical structure [00279] [00280] [00281] CAS No. 1624289-88-8 2226747-73-3 2286234-09-9 Reactant Reactant B19 Reactant B20 Bn Chemical structure [00282] [00283] CAS No. 2304744-50-9

Synthesis of Reactant B8

[0076] Reactant B8 could be synthesized by Scheme IV.

##STR00284##

[0077] 2,4-dichloro-6-phenyl-pyrimidine (1.0 eq), pyridinylphenylboronic acid (1.05 eq, CAS No. 170230-28-1), Pd(PPh.sub.3).sub.4 (0.012 eq), Na.sub.2CO.sub.3 (2.0 eq, 3 M) in THF (0.3 M) was heated at 60 C. for 16 h. After completion of the reaction, the volatiles were removed under vacuum, and the resulting solution was extracted with CH.sub.2Cl.sub.2. The combined organic extract was washed with brine solution, dried over Na.sub.2SO.sub.4. Then the resulting solution was concentrated under reduced pressure and purified by column chromatography to obtain Reactant B8 in a yield of 68%. The purified product was identified as Reactant B8 by FD-MS analysis. FD-MS analysis C.sub.21H.sub.14ClN.sub.3: theoretical value of 343.81 and observed value of 343.81.

Preparation of Claimed Compounds

[0078] Each of the foresaid Intermediates, e.g., Intermediates Bn and Cn could be reacted with various Reactants Bn to synthesize various claimed novel compounds. The general synthesis pathway of the claimed novel compound was summarized in Scheme V.

##STR00285##

[0079] In the above Scheme V, Intermediate Cn may be any one of the foresaid Intermediates C1 to C3 as listed in Table 3 and Intermediates C4 to C7, and Reactant Bn may be any one of Reactants B1 to B20 as listed in Table 4, but it is not limited thereto.

[0080] Intermediate Cn (1.0 eq), Reactant Bn (1.2 eq), Pd(OAc).sub.2 (0.01 eq), and 2-(dicyclohexylphosphino)biphenyl[P(Cy).sub.2(2-biPh)] (0.04 eq) were stirred in a mixed solution of toluene/ethanol (0.5M, v/v=10/1), and 3.0 M of K.sub.2CO.sub.3 aqueous solution. The reaction mixture was heated to about 100 C. and stirred for 12 h under nitrogen atmosphere. After completion of the reaction, water and toluene were added to the reaction mixture. Subsequently, the organic layer was recovered by solvent extraction operation and dried over sodium sulfate. The solvent was then removed under reduced pressure, and the resulting residue was purified by silica gel column chromatography. The obtained residue was recrystallized with toluene to obtain a white solid product as the claimed novel compound.

[0081] Intermediates Cn and Reactants Bn adopted to synthesize Compounds 1 to 7 were listed in Table 5. The obtained Compounds 1 to 7 were identified by H.sup.1-NMR (500 MHz, CDCl.sub.3) and FD-MS, and the chemical structure, yield, formula and mass of each of Compounds 1 to 7 were also listed in Tables 5 and 6. From the data of Table 6, it indicated that Compounds 4 to 7 each had two stereoisomers existing therein.

TABLE-US-00005 TABLE 5 Intermediates Cn and Reactant Bn adopted to prepare Compounds 1 to 7 and their yields, formulae, and FD-MS data Claimed Compound Chemical Yield Formula/ Intermediate Cn Reactant Bn Structure (%) Mass (M.sup.+) [00286] [00287] [00288] 85 C.sub.46H.sub.29N.sub.3/ 623.74 [00289] [00290] [00291] 76 C.sub.58H.sub.37N.sub.3/ 775.93 [00292] [00293] [00294] 65 C.sub.58H.sub.37N.sub.3/ 775.93 [00295] [00296] [00297] 81 C.sub.46H.sub.29N3/ 623.74 [00298] [00299] [00300] 77 C.sub.58H.sub.37N.sub.3/ 775.93 [00301] [00302] [00303] 82 C.sub.58H.sub.37N.sub.3/ 775.93 [00304] [00305] [00306] 78 C.sub.52H.sub.31N.sub.3O/ 713.82

TABLE-US-00006 TABLE 6 H.sup.1-NMR results of Compounds 1 to 7. Compound H.sup.1-NMR [00307] 9.01 ppm (d, 1H), 8.99 ppm (s, 1H), 8.75 ppm (d, 4H), 8.65 ppm (d, 1H), 8.05 ppm (d, 1H), 7.7 ppm (t, 2H), 7.60-7.58 ppm (m, 8H), 7.35-7.31 ppm (m, 4H), 7.29-7.05 ppm (m, 5H), 6.70 ppm (t, 1H), 5.85 ppm (d, 1H) [00308] 8.97 ppm (s, 3H), 8.84 ppm (s, 1H), 8.81 ppm (d, 1H), 8.77 ppm (d, 1H), 8.06 ppm (m, 2H), 7.80-7.76 ppm (m, 6H), 7.62-7.49 ppm (m, 12H), 7.47-7.41 ppm (m, 4H), 7.34-7.24 ppm (m, 3H), 7.09-7.05 ppm (m, 2H), 6.68 ppm (t, 1H), 5.87 ppm (d, 1H) [00309] 9.01 ppm (s, 2H), 8.89 ppm (s, 1H), 8.74 ppm (d, 2H), 8.07 ppm (d, 1H), 7.84 ppm (dd, 2H), 7.76-7.68 ppm (m, 6H), 7.66-7.57 ppm (m, 6H),, 7.52-7.46 ppm (m, 5H) 7.44-7.39 ppm (m, 3H), 7.36-7.30 ppm (m, 4H), 7.16 ppm (t, 1H), 7.11-7.06 ppm (m, 2H), 6.70 ppm (t, 1H), 5.89 ppm (d, 1H) [00310] 9.23 ppm (s, 1H), 8.93 ppm (d, 1H), 8.92 ppm (s, 1H), 8.86 ppm (d, 4H), 8.70 ppm (d, 4H), 8.13 ppm (d, 1H), 8.05 ppm (d, 1H), 7.85 ppm (d, 1H), 7.79 ppm (d, 1H), 7.69-7.54 ppm (m, 27H), 7.32 ppm (t, 4H), 7.18-7.13 ppm (m, 5H), 7.06 ppm (tt, 4H), 6.68 ppm (t, 1H), 6.03 ppm (d, 1H), 5.86 ppm (d, 1H) [00311] 9.23 ppm (s, 1H), 9.08 ppm (s, 2H), 8.96 ppm (d, 1H), 8.92 ppm (s, 2H), 8.85 ppm (d, 2H), 8.69 ppm (d, 2H), 8.10 ppm (d, 1H), 8.02 ppm (d, 1H), 7.85-7.76 ppm (m, 11H), 7.73-7.67 ppm (m, 10H), 7.64-7.58 ppm (m, 12H), 7.53 ppm (dd, 8H), 7.44 ppm (t, 4H), 7.34 ppm (t, 4H), 7.19-7.12 ppm (m, 6H), 7.05 ppm (t, 4H), 6.69 ppm (t, 1H), 6.05 ppm (d, 1H), 5.85 ppm (d, 1H) [00312] 9.23 ppm (s, 1H), 9.04 ppm (s, 2H), 8.94 ppm (d, 1H), 8.92 ppm (s, 1H), 8.88 ppm (s, 2H), 8.86 ppm (d, 2H), 8.73 ppm (d, 2H) 8.10 ppm (d, 1H), 8.19 ppm (s, 1H), 8.02 ppm (d, 1H), 8.00 ppm (s, 1H)7.83 ppm (d, 6H), 7.78 ppm (d, 4H), 7.70 ppm (dd, 4H), 7.70-7.51 ppm (m, 25H), 7.46 ppm (t, 4H), 7.34 ppm (t, 4H), 7.20-7.13 ppm (m, 5H), 7.08-7.04 ppm (m, 4H), 6.68 ppm (t, 1H), 6.05 ppm (dd 1H), 5.88 ppm (dd, 1H) [00313] 9.19 ppm (s, 1H), 9.00 ppm (s, 1H), 8.89 ppm (d, 1H), 8.85 ppm (s, 1H) 8.83 ppm (m, 3H), 8.70 ppm (s, 1H), 870-8.68 ppm (m, 3H), 8.12 ppm (d, 1H), 8.06 ppm (d, 1H), 8.04-7.95 ppm (m, 4H), 7.897.82 ppm (dd, 2H), 7.73 ppm (m, 4H), 7.67-7.45 ppm (m, 21H), 7.34-7.37 ppm (m, 6H), 7.26-7.19 ppm (m, 5H), 7.12 ppm (t, 4H), 6.71 ppm (t, 1H), 6.03 ppm (d, 1H), 5.91 ppm (d, 1H)

Modifications of Compounds 1 to 7

[0082] In addition to the Compounds 1 to 7, one person skilled in the art can react any Intermediate Bn or Intermediate Cn with any Reactant Bn through a reaction mechanism similar to Scheme V to synthesize other desired claimed novel compounds.

Preparation of OLED Devices

[0083] A glass substrate coated with ITO layer (abbreviated as ITO substrate) in a thickness of 1500 was placed in distilled water containing a detergent dissolved therein, and was ultrasonically washed. The detergent was a product manufactured by Fischer Co., and the distilled water was distilled water filtered twice through a filter (Millipore Co.). After the ITO layer had been washed for 30 minutes, it was ultrasonically washed twice with distilled water for 10 minutes. After the completion of washing, the glass substrate was ultrasonically washed with isopropyl alcohol, acetone and methanol solvents and then dried, after which it was transported to a plasma cleaner. Then the substrate was cleaned with oxygen plasma for 5 min, and then transferred to a vacuum evaporator.

[0084] After that, various organic materials and metal materials were sequentially deposited on the ITO substrate to obtain the OLED device of Examples and Comparative Examples as stated above. The vacuum degree during the deposition was maintained at 110.sup.6 to 310.sup.7 torr. Herein, the ITO substrate was deposited with a first hole injection layer (HIL-1), a second hole injection layer (HIL-2), a hole transporting layer (HTL), a blue/green/red emission layer (BEL/GEL/REL), an electron transporting layer (ETL), an electron injection layer (EIL), and a cathode (Cthd).

[0085] Herein, HI and HI-D were materials for forming HIL-1; HI was a material for forming HIL-2; HT was a material for forming HTL; novel compounds of the present invention were materials for forming ETL; Liq was a material for forming ETL and EIL. RH/GH/BH were each a host material for forming REL/GEL/BEL, and RD/GD/BD were each a dopant for forming REL/GEL/BEL. The detailed chemical structures of foresaid commercial materials used in the OLED devices were listed in Table 7.

TABLE-US-00007 TABLE 7 chemical structures of commercial materials for OLED devices. [00314] [00315] [00316] [00317] [00318] [00319] [00320] [00321] [00322] [00323] [00324] [00325]

[0086] The main difference of the OLED devices between Examples and Comparative Examples was that the material of ETL of OLED in the following Comparative Example was made of reference compound as shown in Table 7 but the material of ETL of OLED in the following Examples was made of the novel compounds of the present invention listed in Table 5. Specifically, the materials of ETL of Examples 1 to 21 were listed in Table 5.

Preparation of Red OLED Devices

[0087] To prepare the red OLED device, multiple organic layers were respectively deposited on the ITO substrate according to the sequence as listed in Table 8, and the materials and the thicknesses of the organic layers in red OLED devices were also listed in Table 8.

TABLE-US-00008 TABLE 8 coating sequence, materials and thickness of the organic layers in red OLED device Coating Sequence Layer Material Thickness 1 HIL-1 HI doped with 3.0 wt % of HI-D 100 2 HIL-2 HI 2200 4 HTL HT 100 5 REL RH doped with 3.5 wt % of RD 300 6 ETL novel compounds/reference 350 compound doped with 35.0 wt % of Liq 7 EIL Liq 15 8 Cthd Al 1500

Preparation of Green OLED Devices

[0088] To prepare the green OLED device, multiple organic layers were respectively deposited on the ITO substrate according to the sequence as listed in Table 9, and the materials and the thicknesses of the organic layers in the green OLED devices were also listed in Table 9.

TABLE-US-00009 TABLE 9 coating sequence, materials and thickness of the layers in green OLED device Coating Sequence Layer Material Thickness 1 HIL-1 HI doped with 3.0 wt % of HI-D 100 2 HIL-2 HI 1400 4 HTL HT 100 5 GEL GH doped with 10.0 wt % of GD 400 6 ETL novel compounds/reference 350 compound doped with 35.0 wt % of Liq 7 EIL Liq 15 8 Cthd Al 1500

Preparation of Blue OLED Devices

[0089] To prepare the blue OLED device, multiple organic layers were respectively deposited on the ITO substrate according to the sequence as listed in Table 10, and the materials and the thicknesses of the organic layers in the blue OLED devices were also listed in Table 10.

TABLE-US-00010 TABLE 10 coating sequence, materials and thickness of the layers in blue OLED device Coating Sequence Layer Material Thickness 1 HIL-1 HI doped with 3.0 wt % of HI-D 100 2 HIL-2 HI 850 4 HTL HT 100 5 BEL BH doped with 3.5 wt % of BD 250 6 ETL novel compounds/reference 250 compound doped with 35.0 wt % of Liq 7 EIL Liq 15 8 Cthd Al 1500

Performance of OLED Device

[0090] To evaluate the performance of OLED devices, red, green, and blue OLED devices were measured by PR650 as photometer and Keithley 2400 as power supply. Color coordinates (x,y) were determined according to the CIE chromaticity scale (Commission Internationale de L'Eclairage, 1931). The results were shown in Table 11. For the blue OLED devices, the data were collected at 1000 nits. For the green OLED devices, the data were collected at 3000 nits. And for the red OLED devices, the data were collected at 3000 nits.

TABLE-US-00011 TABLE 11 materials of ETL, colors, CIEs, luminous efficacy, and EQE of OLED devices of Examples 1 to 21 (E1 to E21) and Comparative Examples 1 to 3 (C1 to C3) Luminous Example Material efficacy EQE No. of ETL Color CIE (x, y) (lm/W) (%) E1 Compound 1 B (0.130, 0.148) 8.41 7.13 E2 G (0.311, 0.637) 50.6 17.51 E3 R (0.656, 0.342) 17.8 20.68 E4 Compound 2 B (0.129, 0.156) 7.89 7.57 E5 G (0.310, 0.640) 48.8 17.99 E6 R (0.657, 0.340) 17.5 21.03 E7 Compound 3 B (0.129, 0.158) 8.06 7.06 E8 G (0.319, 0.636) 54.1 18.55 E9 R (0.657, 0.340) 17.4 20.86 E10 Compound 4 B (0.129, 0.164) 6.94 7.54 E11 G (0.313, 0.639) 54.4 18.14 E12 R (0.658, 0.339) 13.1 20.44 E13 Compound 5 B (0.128, 0.161) 7.3 7.16 E14 G (0.322, 0.634) 43.5 18.45 E15 R (0.659, 0.338) 15.1 20.62 E16 Compound 6 B (0.129, 0.168) 7.23 7.1 E17 G (0.327, 0.630) 45.20 18.79 E18 R (0.656, 0.341) 15.3 20.26 E19 Compound 7 B (0.132, 0.138) 6.58 7.00 E20 G (0.320, 0.632) 52.1 18.18 E21 R (0.660, 0.338) 18.5 17.97 C1 Reference B (0.129, 0.149) 4.66 5.92 C2 Compound G (0.316, 0.639) 31.2 17.41 C3 R (0.657, 0.341) 10.10 12.12

[0091] As shown in Table 11, adopting the novel compounds of the present invention as the electron transport material can effectively improve both luminous efficacy and EQE of the red, green, or blue OLEDs.

[0092] Even though numerous characteristics and advantages of the present invention have been set forth in the foregoing description, together with details of the structure and features of the invention, the disclosure is illustrative only. Changes may be made in the details, especially in matters of shape, size, and arrangement of parts within the principles of the invention to the full extent indicated by the broad general meaning of the terms in which the appended claims are expressed.