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## wherein G.sup.1 and G.sup.2 are each selected from the group consisting of:

##STR00002##

one of G.sup.11 and G.sup.12 is a specific aryl group or heteroaryl group. The organic electronic device comprising the novel compound has the beneficial effect of prolonged lifespan.

Claims

1. A compound represented by the following Formula (I): ##STR00359## wherein, G.sup.1 and G.sup.2 are each independently selected from the group consisting of: ##STR00360## one of G.sup.11 and G.sup.12 is selected from the group consisting of: ##STR00361## ##STR00362## ##STR00363## ##STR00364## 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, an alkynyl group having 2 to 6 carbon atoms, and an aryl group having 6 to 12 ring carbon atoms; n1 is an integer from 0 to 5, n2 is an integer from 0 to 4, n3 is an integer from 0 to 7; the other of G.sup.11 and G.sup.12 is an aryl group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, an arylthioxy group having 6 to 18 ring carbon atoms, or a heteroaryl group containing a N, O, or S atom and having 3 to 30 ring carbon atoms; j1 is an integer 1 or 2; k1, j2 and k2 are each independently an integer from 0 to 2; and G.sup.3 and G.sup.4 are each independently selected from the group consisting of: a deuterium atom, a halo group, an alkyl group having 1 to 6 carbon atoms and an aryl group having 6 to 12 ring carbon atoms.

2. The compound as claimed in claim 1, wherein the compound is represented by any one of the following Formulae (I-I) to (I-VI): ##STR00365##

3. The compound as claimed in claim 1, wherein the compound is represented by any one of the following Formulae (I-VII) to (I-XII): ##STR00366## ##STR00367##

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: ##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## ##STR00399## ##STR00400## ##STR00401## ##STR00402## ##STR00403## ##STR00404## ##STR00405## ##STR00406## ##STR00407## ##STR00408## ##STR00409## ##STR00410## ##STR00411## ##STR00412## ##STR00413## ##STR00414## ##STR00415## ##STR00416## ##STR00417## ##STR00418## ##STR00419## ##STR00420## ##STR00421## ##STR00422## ##STR00423##

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 the alkyl group having 1 to 6 carbon atoms represented by G.sup.3 and G.sup.4 are each independently selected from the group consisting of: a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a sec-butyl group, an isopropyl group, and a tert-butyl group.

7. The compound as claimed in claim 1, wherein j1 and j2 are each the integer 1 and k1 and k2 are each the integer 0.

8. The compound as claimed in claim 1, wherein the compound is selected from the group consisting of: ##STR00424## ##STR00425## ##STR00426## ##STR00427## ##STR00428## ##STR00429## ##STR00430## ##STR00431##

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; and 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; and 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 2.

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: ##STR00432## ##STR00433## ##STR00434## ##STR00435## ##STR00436## ##STR00437## ##STR00438## ##STR00439## ##STR00440##

Description

BRIEF DESCRIPTION OF THE DRAWING

[0064] FIG. 1 illustrates a schematic cross-sectional view of an OLED.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0065] Hereinafter, one 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.

Synthesis of Intermediate A1

[0066] Intermediate A1 used for preparing a novel compound was synthesized by the following steps. The synthesis pathway of the Intermediate A1 was summarized in Scheme A1.

##STR00160##

[0067] Step 1: Synthesis of Intermediate A1-1

[0068] A mixture of 3-bromodibenzo[a,d]cyclohepten-5-one (86 g, 1.0 eq), N-bromosuccinimide (NBS) (106 g, 2 eq), benzyl peroxide (0.7 g, 0.01 eq) in carbon tetrachloride (CCl.sub.4) (430 ml) was heated to 85 C. The reaction progress was monitored by high performance liquid chromatography (HPLC). After completion of the reaction, the precipitate was separated by filtration and washed with CH.sub.3OH, which was then purified by recrystallization. The purified product was concentrated to dryness, whereby white solids were obtained in an amount of 123 g and a yield of 92.3%.

[0069] The solid product was identified as Intermediate A1-1 by a field desorption mass spectroscopy (FD-MS) analysis. FD-MS analysis: C.sub.15H.sub.9Br.sub.3O: theoretical value of 444.94 and observed value of 444.94.

Step 2: Synthesis of Intermediate A1-2

[0070] The obtained Intermediate A1-1 (116.0 g, 1.0 eq) was dissolved in 960 ml of furan/THF(v/v=2/1), the reaction was cooled to 0 C. and then treated with potassium tert-butoxide (KO-t-Bu) (87.8 g, 3.0 eq). The reaction was allowed to stir at 0 C. for 1 hour, and then stirred at room temperature for another 12 hours. After completion, the reaction was quenched by DI water and the organic layer was recovered by solvent extraction operation 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 and a yield of 51.1%.

[0071] The solid product was identified as Intermediate A1-2 by FD-MS analysis. FD-MS analysis C.sub.19H.sub.11BrO.sub.2: theoretical value of 351.19 and observed value of 351.19.

Step 3: Synthesis of Intermediate A1-3

[0072] A suspension of Intermediate A1-2 (53.5 g, 1.0 eq) and 5% Pd/C (8.1 g, 0.025 eq) in 535 ml of ethyl acetate (EA) was stirred for 3 hours to 6 hours under a hydrogen atmosphere (H.sub.2) 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 100 g of yellow solid product and a yield of 90%.

[0073] The solid product was identified as Intermediate A1-3 by FD-MS analysis. FD-MS analysis C.sub.19H.sub.13BrO.sub.2: theoretical value of 353.21 and observed value of 353.21. The intermediate A1-3 can be directly used in the following step without further purification.

Step 4: Synthesis of Intermediate A1-4

[0074] Intermediate A1-3 (53 g, 1.0 eq) and p-toluenesulfonic acid (PTSA) (57 g, 2.0 eq) in 530 ml of toluene was heated to 110 C. under reflux for 12 hours. The reaction mixture was cooled to room temperature 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 (1:1 v/v) as eluent, whereby a light yellow solid product was obtained in a yield of 91.5%.

[0075] The solid product was identified as Intermediate A1 by FD-MS analysis. FD-MS analysis C.sub.19H.sub.11BrO: theoretical value of 335.19 and observed value of 335.19.

Synthesis of Intermediate A2

[0076] Intermediate A2 used for preparing a novel compound was synthesized in a similar manner as Intermediate A1 through steps 1 to 4, except that the starting material 3-bromodibenzo[a,d]cyclohepten-5-one was replaced by 2-bromodibenzo[a,d]cyclohepten-5-one (CAS No. 198707-82-3). The synthesis pathway of Intermediate A2 was summarized in Scheme A2. All intermediates were analyzed according to the methods as described above, and the results were listed in Table 1.

##STR00161##

Synthesis of Intermediate A3

[0077] Intermediate A3 used for preparing a novel compound was synthesized in a similar manner as Intermediate A1 through steps 1 to 4, except that the starting material 3-bromodibenzo[a,d]cyclohepten-5-one was replaced by 3,7-dibromodibenzo[a,d]cyclohepten-5-one (CAS No. 226946-20-9). The synthesis pathway of Intermediate A3 was summarized in Scheme A3. All intermediates were analyzed as described above, and the results were listed in Table 1.

##STR00162##

TABLE-US-00001 TABLE 1 chemical structures, yields, formulae, and mass (M.sup.+) analyzed FD-MS of intermediates. Intermediate A1-1 A1-2 A1-3 A1 Chemical Structure [00163] [00164] [00165] [00166] Yield 92.3% 51.1% NA 91.5% Formula C.sub.15H.sub.9Br.sub.3O C.sub.19H.sub.11BrO.sub.2 C.sub.19H.sub.13BrO.sub.2 C.sub.19H.sub.11BrO Mass(M.sup.+) 444.94 351.19 353.21 335.19 Intermediate A2-1 A2-2 A2-3 A2 Chemical Structure [00167] [00168] [00169] [00170] Yield 91.5% 58.2% 91% 93.5% Formula C.sub.15H.sub.9Br.sub.3O C.sub.19H.sub.11BrO.sub.2 C.sub.19H.sub.13BrO.sub.2 C.sub.19H.sub.11BrO Mass(M.sup.+) 444.94 351.19 353.21 335.19 Intermediate A3-1 A3-2 A3-3 A3 Chemical Structure [00171] [00172] [00173] [00174] Yield 93.7% 75.8% NA 93.0% Formula C.sub.15H.sub.8Br.sub.4O C.sub.19H.sub.10Br.sub.2O.sub.2 C.sub.19H.sub.12Br.sub.2O.sub.2 C.sub.19H.sub.10Br.sub.2O Mass(M.sup.+) 523.84 430.09 432.11 414.09

Modifications of Intermediates A1 to A3

[0078] In addition to the Intermediates A1 to A3, one person skilled in the art can adopt other starting materials and successfully synthesize other desired intermediates through a reaction mechanism similar to Schemes A1 to A3. Applicable modifications of Intermediates A1 to A3 may be, for example, but not limited to. Intermediates A4 to A12 as follows.

##STR00175## ##STR00176##

Preparation of Intermediate Bn

[0079] Intermediate Bn, including Intermediates B1 to B3, which was used to synthesize the novel compounds, could be purchased or synthesized by the following Scheme II.

##STR00177##

[0080] wherein j2 and k2 are each independently an integer from 0 to 2; and

[0081] G.sup.3 and G.sup.4 are each independently selected from the group consisting of: a deuterium atom, a halo group, an alkyl group having 1 to 6 carbon atoms and an aryl group having 6 to 12 ring carbon atoms.

[0082] The main difference of the preparation of Intermediates B1 to B3 was the material of Intermediate An as listed in Table 1 or the material of Reactant An (Reactants A1 and A2) as listed in Table 2.

TABLE-US-00002 TABLE 2 the chemical structures, names, and CAS No, of Reactants A1 and A2 Chemical Structure Reactant An of Reactant An Name CAS No. Reactant A1 [00178] 2-Bromobiphenyl 2052-07-5 Reactant A2 [00179] 2-Bromo-4-tert- butylbiphenyl 1033692-34-0

Synthesis of Intermediate B1

[0083] The foresaid Intermediate A1 was further reacted with 2-bromo-biphenyl to synthesize Intermediate B1. The synthesis pathway of the Intermediate B1 was summarized in Scheme B1.

##STR00180##

Step 1: Synthesis of Intermediate B1-1

[0084] 2-Bromo-biphenyl (1.0 eq) was dissolved in 120 ml of anhydrous THF (0.3 M), and cooled to 78 C. n-Butyl lithium (n-BuLi) (1.0 eq) was slowly added to the above cooled solution. After 20 minutes of stirring, Intermediate A1 (0.7 eq) was added to the reaction solution and then stirred for 3 hours at room temperature. The reaction was monitored by HPLC. After the reaction completion, the reaction solution was washed with water, and a water layer was extracted with EA. 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 a filtrate was concentrated to obtain a light yellow, powdery solid in a yield of 83%.

[0085] The solid product was identified as Intermediate B1-1 by FD-MS analysis. FD-MS analysis: C.sub.31H.sub.21BrO: theoretical value of 489.40 and observed value of 489.40. The intermediate B1-1 can be directly used in the following step without further purification.

Step 2: Synthesis of Intermediate B1

[0086] Intermediate B1-1 (1.0 eq), acetic acid (w/v=1/3 to the reactant) and H.sub.2SO.sub.4 (10 drops) were mixed, and the mixture was stirred at 110 C. for 6 hours. The reaction was monitored by HPLC. After completion of a reaction, the solvent was then removed under reduced pressure, and the residue was purified with column chromatography. The residual mass was purified with column chromatography to obtain a white solid product in a yield of 93.0%.

[0087] The solid product was identified as Intermediate B1 by FD-MS analysis. FD-MS analysis: C.sub.31H.sub.19Br: theoretical value of 471.39 and observed value of 471.39.

Synthesis of Intermediate B2

[0088] Intermediate B2 was synthesized in a similar manner as Intermediate B1 through steps 1 and 2, except that the Intermediate A1 was replaced by Intermediate A2. The synthesis pathway of Intermediate B2 was summarized in Scheme B2. All intermediates were analyzed according to the methods as described above, and the results were listed in Table 3.

##STR00181##

Synthesis of Intermediate B3

[0089] Intermediate B3 was synthesized in a similar manner as Intermediate B2 through steps 1 and 2, except that the Reactant A1 was replaced by Reactant A2. The synthesis pathway of Intermediate B3 was summarized in Scheme B3. All intermediates were analyzed according to the methods as described above, and the results were listed in Table 3.

##STR00182##

TABLE-US-00003 TABLE 3 chemical structures, yields, formulae, and mass analyzed by FD-MS of intermediates Intermediate No. Chemical Structure Yield(%) Formula Mass B1-1 [00183] 83.1 C.sub.31H.sub.21BrO 489.41 B1 [00184] 93.0 C.sub.31H.sub.19Br 471.39 B2-1 [00185] 87.6 C.sub.31H.sub.21BrO 489.40 B2 [00186] 91.5 C.sub.31H.sub.19Br 471.39 B3-1 [00187] 81.0 C.sub.35H.sub.29BrO 545.51 B3 [00188] 92.0 C.sub.35H.sub.27Br 527.49

Modifications of Intermediates B1 to B3

[0090] In addition to the Intermediates B1 to B3, one person skilled in the art can successfully synthesize other desired intermediates from Intermediates A1 to A12 and Reactants A1 and A2 through a reaction mechanism similar to Schemes B1 to B3. Applicable modifications of Intermediates B1 to B3 may be, for example, but not limited to, Intermediates B4 to B17 as follows.

##STR00189## ##STR00190## ##STR00191## ##STR00192##

Preparation of Intermediate Cn

[0091] Intermediate Cn, including Intermediates C1 to C4, could be purchased or synthesized by the following Scheme III.

##STR00193##

[0092] wherein j2 and k2 are each independently an integer from 0 to 2; and

[0093] G.sup.3 and G.sup.4 are each independently selected from the group consisting of: a deuterium atom, a halo group, an alkyl group having 1 to 6 carbon atoms and an aryl group having 6 to 12 ring carbon atoms.

[0094] A mixture of intermediate Bn (1.0 eq), bis(pinacolato)diboron (1.05 eq), PdCl.sub.2(dppf) (0.025 eq), KOAc (3.0 eq) in 1,4-dioxane (200 mL) was heated under reflux. After 18 hours of stirring, the reaction solution was cooled to room temperature, and an organic layer was extracted by adding saturated sodium chloride aqueous solution and EA, dried over magnesium sulfate, and then treated with activated charcoal, followed by filtering with celite. Then, a residue obtained by concentrating the filtrate under reduced pressure was suspended in hexane, the suspension was filtered again and washed with hexane, thereby obtaining a yellow solid product.

[0095] 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 4.

TABLE-US-00004 TABLE 4 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.+) [00194] [00195] 84 C.sub.37H.sub.31BO.sub.2/ 518.45 [00196] [00197] 86 C.sub.37H.sub.31BO.sub.2/ 518.45 [00198] [00199] 75 C.sub.41H.sub.39BO.sub.2/ 574.56

Preparation of Reactants Bn

[0096] Reactants Bn, such as Reactants B1 to B21, applicable to prepare a novel compound were listed in Table 5-1.

TABLE-US-00005 TABLE 5-1 chemical structures and the CAS No. of the Reactants B1 to B21 Reactant Bn Reactant B1 Reactant B2 Reactant B3 Reactant B4 Chemical structure [00200] [00201] [00202] [00203] CAS No. 1618107-00-8 2142681-84-1 1472729-25-1 1883265-32-4 Reactant Bn Reactant B5 Reactant B6 Reactant B7 Reactant B8 Chemical structure [00204] [00205] [00206] [00207] CAS No. 1883265-36-8 2226747-73-3 Reactant Bn Reactant B9 Reactant B10 Reactant B11 Reactant B12 Chemical structure [00208] [00209] [00210] [00211] CAS No. 1624289-88-8 2226747-65-3 Reactant Bn Reactant B13 Reactant B14 Reactant B15 Reactant B16 Chemical structure [00212] [00213] [00214] [00215] CAS No. 2170887-83-7 2286234-09-9 2304744-50-9 Reactant Bn Reactant B17 Reactant B18 Reactant B19 Reactant B20 Chemical structure [00216] [00217] [00218] [00219] CAS No, 1616231-57-2 2251105-15-2 1205748-61-3 Reactant Bn Reactant B21 Chemical structure [00220] CAS No. 1689576-03-1

[0097] The Reactants Bn such as B5, B7, B10, B11 and B13 could be purchased or synthesized by the following Scheme R1.

##STR00221##

[0098] A mixture of Reactant Cn (1.0 eq), Reactant Dn (1.1 eq), tris(dibenzylideneacetone)dipalladium[Pd.sub.2(dba).sub.3] (0.015 eq), triphenylphosphine (PPh.sub.3) was stirred in a mixed solution of methoxymethane (DME) (0.5M) and Na.sub.2CO.sub.3 aqueous solution (2.0 M). The reaction mixture was heated to about 65 C. to 70 C. and stirred for 24 hours 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 from the organic layer under reduced pressure, and the resulting residue was washed with methanol and dried to obtain a white solid product as Reactant Bn.

[0099] Reactant Cn and Reactant Dn adopted to synthesize Reactants B5, B7, B10, B11 and B13 were listed in Table 5-2. The obtained Reactants Bn were identified by FD-MS, and the chemical structure, yield, formula and mass of each of Reactants B5, B10, B11 and B13 were also listed in Tables 5-2.

TABLE-US-00006 TABLE 5-2 Reactants Cn and Reactants Dn adopted to prepare Reactants B5, B7, B10, B11 and B13 and their yields, formulae, and FD-MS data Reactant Cn/ Reactant Dn/ Yield Formula/ CAS No. CAS No. Reactant Bn (%) Mass (M.sup.+) [00222] [00223] [00224] 78 C.sub.27H.sub.16ClN.sub.3O/ 433.89 [00225] [00226] [00227] 75 C.sub.27H.sub.16ClN.sub.3O/ 433.89 [00228] [00229] [00230] 80 C.sub.21H.sub.7D.sub.5ClN.sub.3O/ 362.82 [00231] [00232] [00233] 82 C.sub.21H.sub.7D.sub.5ClN.sub.3O/ 362.82 [00234] [00235] [00236] 85 C.sub.21H.sub.7D.sub.5ClN.sub.3O/ 362.82

Preparation of Claimed Compounds

[0100] Each of the foresaid Intermediates, e.g., Intermediates 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 IV.

##STR00237##

[0101] In the above Scheme IV, Intermediate Cn may be any one of the foresaid Intermediates C1 to C3 as listed in Table 4, and Reactant Bn may be any one of Reactants B1 to B21 as listed in Table 5-1, but it is not limited thereto.

[0102] Intermediate Cn (1.0 eq). Reactant Bn (1.1 eq), Pd.sub.2(dba).sub.3 (0.015 eq), and 2-(dicyclohexylphosphino)biphenyl[P(Cy).sub.2(2-biPh)](0.06 eq) were stirred in a mixed solution of DME (0.5 M) and K.sub.2CO.sub.3 aqueous solution (2.0 M). The reaction mixture was heated to about 100 C. and stirred for 12 hours 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 from the organic layer 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.

[0103] Intermediates Cn and Reactants Bn adopted to synthesize Compounds 1 to 28 were listed in Table 6. The obtained Compounds 1 to 28 were identified by H.sup.1-NMR and FD-MS. The chemical structure, yield, formula and mass of each of Compounds 1 to 28 were also listed in Table 6. The results of H.sup.1-NMR of Compounds 1 to 4 and 9 to 28 were listed in Table 7. From the data of Table 7, it indicated that Compound 21 had two stereoisomers at a ratio of 1:2 existing therein, and thus the total hydrogen number was 123.

TABLE-US-00007 TABLE 6 intermediates Cn and Reactant Bn adopted to prepare Compounds 1 to 28 and their yields, formulae, and FD-MS data Claimed Compound Chemical Structure Intermediate of Claimed Yield Cn Reactant Bn Compound (%) Formula/Mass (M.sup.+) [00238] [00239] [00240] 85 C.sub.52H.sub.31N.sub.3O/ 713.82 [00241] [00242] [00243] 76 C.sub.52H.sub.31N.sub.3O/ 713.82 [00244] [00245] [00246] 65 C.sub.52H.sub.31N.sub.3O/ 713.82 [00247] [00248] [00249] 81 C.sub.52H.sub.31N.sub.3O/ 713.82 [00250] [00251] [00252] 77 C.sub.58H.sub.35N.sub.3O/ 789.92 [00253] [00254] [00255] 82 C.sub.58H.sub.35N.sub.3O/ 789.92 [00256] [00257] [00258] 87 C.sub.58H.sub.35N.sub.3O/ 789.92 [00259] [00260] [00261] 82 C.sub.52H.sub.26D.sub.5N.sub.3O/ 718.85 [00262] [00263] [00264] 72 C.sub.58H.sub.35N.sub.3O/ 789.92 [00265] [00266] [00267] 82 C.sub.52H.sub.26D.sub.5N.sub.3O/ 718.85 [00268] [00269] [00270] 83 C.sub.52H.sub.26D.sub.5N.sub.3O/ 718.85 [00271] [00272] [00273] 82 C.sub.52H.sub.26D.sub.5N.sub.3O/ 718.85 [00274] [00275] [00276] 85 C.sub.58H.sub.35N.sub.3O/ 789.92 [00277] [00278] [00279] 75 C.sub.53H.sub.32N.sub.2O/ 712.83 [00280] [00281] [00282] 79 C.sub.53H.sub.32N.sub.3O/ 712.83 [00283] [00284] [00285] 84 C.sub.52H.sub.31N.sub.3O/ 713.82 [00286] [00287] [00288] 85 C.sub.58H.sub.35N.sub.3O/ 789.92 [00289] [00290] [00291] 81 C.sub.58H.sub.35N.sub.3O/ 789.92 [00292] [00293] [00294] 70 C.sub.58H.sub.33N.sub.3O.sub.2/ 803.9 [00295] [00296] [00297] 86 C.sub.52H.sub.33N.sub.3/ 699.84 [00298] [00299] [00300] 80 C.sub.56H.sub.41N.sub.3/ 755.94 [00301] [00302] [00303] 82 C.sub.52H.sub.31N.sub.3O/ 713.82 [00304] [00305] [00306] 80 C.sub.58H.sub.37N.sub.3/ 775.93 [00307] [00308] [00309] 85 C.sub.58H.sub.37N.sub.3/ 775.93 [00310] [00311] [00312] 76 C.sub.53H.sub.32N.sub.2O/ 712.83 [00313] [00314] [00315] 70 C.sub.53H.sub.32N.sub.2O/ 712.83 [00316] [00317] [00318] 75 C.sub.53H.sub.34N.sub.2/ 698.85 [00319] [00320] [00321] 85 C.sub.52H.sub.33N.sub.3/ 699.84

TABLE-US-00008 TABLE 7 H.sup.1-NMR results of Compounds Claimed Compound H.sup.1-NMR [00322] .sup.1H NMR (500 MHz, CDCl.sub.3): 9.17 (s, 1H), 8.73-8.68 (m, 2H), 8.65 (d, 1H), 8.60 (d, 2H), 8.11 (d, 1H), 8.02 (d, 1H), 7.83 (d, 1H), 7.79-7.69 (m, 4H), 7.69-7.61 (m, 6H), 7.61-7.51 (m, 4H), 7.48 (t, 1H), 7.43-7.31 (m, 2H), 7.26 (t, 1H), 7.20-7.05 (m, 2H), 6.67 (t, 1H), 5.90 (d, 1H) ppm. [00323] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.76 (s, 1H), 8.65 (d, 1H), 8.65-8.56 (m, 3H), 8.10-7.97 (m, 3H), 7.92-7.85 (m, 1H), 7.81 (d, 1H), 7.77-7.71 (m, 3H), 7.70-7.61 (m, 5H), 7.61-7.48 (m, 6H), 7.41-7.29 (m, 3H), 7.20-7.06 (m, 3H), 6.65 (t, 1H), 5.90 (d, 1H) ppm. [00324] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.82-8.64 (m, 4H), 8.58 (d, 1H), 8.13 (d, 1H), 7.98 (t, 2H), 7.87 (d, 1H), 7.82- 7.54 (m, 13H), 7.55-7.45 (m, 2H), 7.45-7.31 (m, 2H), 7.28 (d, 1H), 7.21-7.05 (m, 2H), 6.65 (t, 1H), 5.92 (d, 1H) ppm. [00325] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.74 (s, 1H), 8.63 (d, 1H), 8.58 (d, 2H), 8.43 (d, 1H), 8.24 (d, 1H), 7.92 (d, 1H), 7.84 (d, 1H), 7.78 (d, 1H), 7.75-7.52 (m, 14H), 7.46 (t, 1H), 7.34 (t, 1H), 7.26 (t, 1H), 7.20-7.05 (m, 3H), 6.65 (t, 1H), 5.90 (d, 1H) ppm. [00326] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.84 (m, 3H), 8.77 (s, 1H), 8.70-8.55 (m, 4H), 8.09-8.00 (m, 2H), 8.00-7.95 (m, 1H), 7.88-7.81 (d, 1H), 7.81-7.75 (td, 1H), 7.75- 7.69 (m, 1H), 7.69-7.62 (m, 7H), 7.60 (, 1H), 7.57-7.51 (m, 3H), 7.46-7.29 (m, 4H), 7.18-7.05 (m, 2H), 6.67 (t, 1H), 5.90 (d, J = 10.5 Hz, 1H) ppm. [00327] .sup.1H NMR (500 MHz, CDCl.sub.3): 9.21 (d, J = 1.5 Hz, 1H), 8.80-8.65 (m, 3H), 8.13 (d, 1H), 8.01 (d, 1H), 7.86 (d, 1H), 7.81-7.55 (m, 11H), 7.50 (t, 1H), 7.42 (t, 1H), 7.35 (t, 1H), 7.30-7.25 (m, 1H), 7.20-7.05 (m, 2H), 6.67 (t, 1H), 5.88 (d, 1H) ppm. [00328] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.73 (s, 1H), 8.66 (s, 1H), 8.65-8.54 (m, 2H), 8.05 (d, 1H), 7.98 (d, 1H), 7.92-7.85 (m, 3H), 7.78 (d, J = 10.0 Hz, 1H), 7.76-7.71 (m, 3H), 7.70-7.60 (m, 6H), 7.49 (t, 1H), 7.41-7.30 (m, 3H), 7.20-7.09 (m, 2H), 6.67 (t, 1H), 5.91 (d, 1H) ppm. [00329] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.75 (d, 1H), 8.38 (dd, 1H), 8.46 (d, 1H), 8.25 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.78 (d, 1H), 7.75-7.60 (m, 10H), 7.60-7.53 (m, 1H), 7.52-7.44 (m, 1H), 7.35 (t, 3H), 7.29 (d, J = 10.5 Hz, 1H), 7.20-7.05 (m, 3H), 6.70 (t, 1H), 5.92 (d, 1H) ppm. [00330] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.78 (d, J = 1.0 Hz, 1H), 8.74-8.58 (m, 6H), 8.03 (q, J = 7.5 Hz, 5H), 8.94- 8.85 (m, 1H), 7.81 (d, J = 10.0 Hz, 1H), 7.78-7.68 (m, 5H), 7.68-7.60 (m, 4H), 7.55-7.47 (m, 4H), 7.18-7.05 (m, 2H), 6.65 (td, J = Hz, 1H), 5.90 (d, J = Hz, 3H) ppm. [00331] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.66 (d, 2H), 8.39 (s, 1H), 8.20-8.12 (m, 2H), 8.09 (d, 1H), 8.05-7.95 (m, 4H), 7.89-7.80 (m, 2H), 7.80-7.69 (m, 3H), 7.69-7.58 (m, 6H), 7.57-7.50 (m, 4H), 7.39 (t,, 1H), 7.33 (t, 1H), 7.29 (d, 1H), 7.15-7.04 (m, 2H), 6.64 (t, 1H), 5.91 (d, 1H) ppm. [00332] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.62-8.52(m, 2H), 8.41 (d, 1H), 8.24 (d, J = 2.0 Hz, 1H), 8.20-8.10 (dd, H), 8.04-7.92 (m, 3H), 7.85-7.69 (m, 5H), 7.69-7.57 (m, 7H), 7.57-7.45 (m, 4H), 7.45-7.31 (m, 2H), 7.28 (dd, 1H), 7.19-7.05 (m, 2H), 6.66 (t, 1H), 5.91 (d, 1H) ppm. [00333] .sup.1H NMR (500 MHz, CDCl.sub.3): 9.05 (s, 1H), 8.92 (s, 1H), 8.74 (dd, 3H), 8.41 (dd, 1H), 8.04 (d, 1H), 8.01 (s, 1H), 7.90 (d, 3H), 7.85-7.45 (m, 14H), 7.45-7.29 (m, 3H), 7.20-7.10 (m, 2H), 7.10-7.01 (m, 1H), 6.67 (t, 1H) 5.90 (d, 1H) ppm. [00334] .sup.1H NMR (500 MHz, CDCl.sub.3): 9.51 (d, 1H), 8.92 (d, 1H), 8.82-8.60 (m, 3H), 8.41 (dd, 1H), 8.02 (d, 1H), 7.98 (d, 1H), 7.92 (d, 1H), 7.82-7.42 (m, 16H), 7.42- 7.25 (m, 4H), 7.20-7.10 (m, 2H), 7.10-7.00 (m, 1H), 6.78 (t, 1H), 5.91 (d, 3H) ppm. [00335] .sup.1H NMR (500 MHz, CDCl.sub.3): 9,04 (s, 1H), 8.93 (s, 1H), 8.88 (s, 1H), 8.71 (d, 1H), 8.67 (d, 1H), 8.48 (d, 1H), 8.05-7.85 (m, 3H), 7.84-7.61 (m, 7H), 7.60-7.49 (m, 9H), 7.49-7.26 (m, 3H), 7.20-7.11 (m, 2H), 7.11- 7.00 (m, 1H), 6.68 (t, 1H), 5.92 (d, 1H) ppm. [00336] .sup.1H NMR (500 MHz, CDCl.sub.3): 9.05 (d, 1H), 8.92 (d, , 1H), 8.78 (d, J = 10.5 Hz, 1H), 8.74 (dd, Hz, 1H), 8.42 (dd, 1H), 8.03 (d, 1H), 7.97 (d, 1H), 7.91 (d, 2H), 7.83-7.44 (m, 15H), 7.43-7.28 (m, 4H), 7.15 (t, 2H), 7.06 (t, 1H), 6.67 (t, 1H), 5.91 (d, J = Hz, 1H) ppm. [00337] .sup.1H NMR (500 MHz, CDCl.sub.3): 9.04 (s, 1H), 8.94 (s, 1H), 8.82-8.65 (m, 3H), 8.49-8.35 (m, 1H), 8.00-7.85 (m, 1H), 7.85-7.48 (m, 18H), 7.48-7.37 (m, 1H), 7.37- 7.28 (m, 2H), 7.2-7.09 (m, 2H), 7.09-7.00 (m, 1H), 6.67 (t, 1H), 5.89 (d, 1H) ppm. [00338] .sup.1H NMR (500 MHz, CDCl.sub.3): 9.08(s, 3H), 8.96(s, 3H), 8.75~8.73(dd, 8H), 8.39(m, 3H), 7.87-7.48(m, 59H), 7.48-2.25(m, 9H), 7.21-7.02(m, 8H), 6.65(t, 1H), 6.58(s, 1H), 5.90(d, 1H), 1.54(s, 9H), 0.93(s, 18H) ppm. [00339] .sup.1H NMR (500 MHz, CDCl.sub.3): 9.08 (s, 1H), 8.75 (d, 1H), 8.67 (d, 1H), 8.43 (d, 1H), 8.33 (d, 1H), 7.91 (d, 1H), 7.82-7.72 (m, 3H), 7.70 (d, 1H), 7.68-7.45 (m, 12H), 7.40-7.29 (m, 2H), 7.23-7.12 (m, 3H), 7.12-7.02 (m, 1H), 6.70 (t, 1H), 5.92 (d, 1H) ppm. [00340] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.82 (d, 2H), 8.75-8.65 (m, 2H), 8.61 (d, 2H), 8.00 (s, 1H), 8.60 (d, 2H), 7.80- 7.70 (m, 4H), 7.70-7.61 (m, 6H), 7.61-7.51 (m, 7H), 7.51-7.40 (m, 3H), 7.30-7.20 (m, 3H), 7.16 (t, 1H), 7.10 (t, 1H), 6.69 (t, 1H), 5.94 (d, J = 10.5 Hz, 1H) ppm. [00341] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.81 (s, 2H), 8.69 (d, J = 2.0 Hz, 1H), 8.67 (d, 1H), 8.64 (d, 2H), 7.90-7.85 (m, 2H), 7.8g-7.75 (m, 2H), 7.75-7.67 (m, 5H), 7.67-7.55 (m, 8H), 7.55-7.50 (m, 4H), 7.50-7.40 (m, 2H), 7.40- 7.30 (m, 1H), 7.30-7.20 (m, 3H), 7.13 (t, 1H), 7.09 (t, 1H), 6.64 (t, 1H), 5.89 (d, 1H) ppm. [00342] .sup.1H NMR (500 MHz, CDCl.sub.3): 9.01 (d, 1H), 8.49 (d, 1H), 8.39 (dd, , 1H), 8.30-8.20 (m, 3H), 8.10-8.03 (m, 2H), 7.98 (d, 1H), 7.90 (d, 1H), 7.83-7.73 (m, 1H), 7.72-7.45 (m, 12H), 7.42-7.26 (m, 3H), 7.20-7.10 (m, 2H), 7.09-7.00 (m, 1H), 6.65 (td, 1H), 5.90 (d, 1H) ppm. [00343] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.70(dd, J = 10.0, 3.5 Hz, 2H), 8.58 (d, J = 2.5 Hz, 1H), 8.51 (d, 1H), 8.21 (dd, 1H), 8.05 (s, 1H), 8.03-8.01 (m, 1H), 8.00-7.93 (m, 2H), 7.92-7.88 (m, 1H), 7.76-7.70 (m, 2H), 7.70-7.56 (m, 7H), 7.55-7.45 (m, 5H), 7.4-7.26 (m, 3H), 7.20- 7.10 (m, 2H), 7.10-7.02 (m, 1H), 6.66 (t, 1H), 5.89 (d, 1H) ppm. [00344] .sup.1H NMR (500 MHz, CDCl.sub.3): 9.03 (d, 1H), 8.48-8.41 (m, 1H), 8.39 (dd, J = 13, 1H), 8.30-8.24 (m, 2H), 8.21 (d, 1H), 8.02 (s, 1H), 7.91 (d, 1H), 8.03-7.75 (m, 1H), 7.75-7.66 (m, 4H), 7.66-7.58 (m, 6H), 7.58-7.45 (m, 7H), 7.45-7.37 (m, 1H), 7.37-7.26 (m, 2H), 7.19-7.30 (m, 2H), 7.10-7.00 (m, 1H), 6.67 (t, 1H), 5.93 (d, 1H) ppm. [00345] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.82(s, 1H), 8.68(s, 1H), 8.61(d, 2H), 8.59(d, 1H), 7.93(d, 1H), 7.83(d, 1H), 7.78(d, 1H), 7.73-7.68(m, 5H), 7.67-7.51(m, 12H), 7.47(d, 1H), 7.35(t, 1H), 7.29(d, 1H), 7.13(t, 1H), 7.10(t, 1H), 6.68(t, 1H), 5.91(d, 1H)

Modifications of Compounds 1 to 28

[0104] In addition to Compounds 1 to 28, one person skilled in the art can react any Intermediate Cn with any Reactant Bn through a reaction mechanism similar to Scheme IV to synthesize other desired claimed novel compounds.

Preparation of OLED Devices

[0105] A glass substrate coated with an 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.

[0106] 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).

[0107] 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; the novel compounds of the present invention of the Examples, ET1 and ET2 of the Comparative Examples 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 8.

TABLE-US-00009 TABLE 8 chemical structures of commercial materials, ET1 and ET2 for OLED devices [00346] HI [00347] HI-D [00348] HT [00349] BH [00350] BD [00351] Liq [00352] [00353] GH [00354] GD [00355] RH [00356] RD [00357] ET1 [00358] ET2

[0108] The main difference of the OLED devices between Examples and Comparative Examples was that the material of ETL of the OLED in the following Comparative Example was made of ET1 or ET2 listed in Table 8, but the material of ETL of the OLED in the following Examples was made of the novel compounds of the present invention. Specifically, the materials of ETL of Examples 1 to 18 were listed in Table 6.

Preparation of Red OLED Devices

[0109] To prepare the red 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 red OLED devices were also listed in Table 9.

TABLE-US-00010 TABLE 9 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 3 HTL HT 100 4 REL RH doped with 3.5 wt % of RD 300 5 ETL ET1/ET2/novel compounds doped 350 with 35.0 wt % of Liq 6 EIL Liq 15 7 Cthd Al 1500

Preparation of Green OLED Devices

[0110] To prepare the green 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 green OLED devices were also listed in Table 10.

TABLE-US-00011 TABLE 10 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 3 HTL HT 100 4 GEL GH doped with 10.0 wt % of GD 400 5 ETL ET1/ET2/novel compounds doped 350 with 35.0 wt % of Liq 6 EIL Liq 15 7 Cthd Al 1500

Preparation of Blue OLED Devices

[0111] To prepare the blue OLED device, multiple organic layers were respectively deposited on the ITO substrate according to the sequence as listed in Table 11, and the materials and the thicknesses of the organic layers in blue OLED devices were also listed in Table 11.

TABLE-US-00012 TABLE 11 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 3 HTL HT 100 4 BEL BH doped with 3.5 wt % of BD 250 5 ETL ET1/ET2/novel compounds doped 250 with 35.0 wt % of Liq 6 EIL Liq 15 7 Cthd Al 1500

[0112] Performance of OLED Device

[0113] 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.

[0114] Measurement of Lifespan

[0115] The evaluation of lifespan was measured by OLED life time test system (Chroma model 58131). Measurement of lifespan for blue, green, and red OLEDs were respectively performed according to the following circumstances.

[0116] For blue OLEDs, the evaluation of lifespan (T85) was defined as a period taken for luminance reduction to reach 85% of the initial luminance at 2000 nits. The results of blue OLEDs were shown in Table 12.

[0117] For green OLEDs, the evaluation of lifespan (95) was defined as a period taken for luminance reduction to reach 95% of the initial luminance at 7000 nits. The results of green OLEDs were shown in Table 13.

[0118] For red OLEDs, the evaluation of lifespan (90) was defined as a period taken for luminance reduction to reach 90% of the initial luminance at 6000 nits. The results of red OLEDs were shown in Table 14.

TABLE-US-00013 TABLE 12 materials of ETL and lifespan of blue OLED devices of Examples 1 to 13 and Comparative Example 1 Example Lifespan (T85) No. Material of ET (hrs) Example 1 Compound 1 173 Example 2 Compound 2 271 Example 3 Compound 3 139 Example 4 Compound 4 298 Example 5 Compound 9 304 Example 6 Compound 12 293 Example 7 Compound 13 299 Example 8 Compound 14 140 Example 9 Compound 18 316 Example 10 Compound 19 303 Example 11 Compound 25 227 Example 12 Compound 23 149 Example 13 Compound 28 146 Comparative ET2 93 Example 1

TABLE-US-00014 TABLE 13 materials of ETL and lifespan of green OLED devices of Examples 14 and 15 and Comparative Examples 2 and 3 Example Lifespan (T95) No. Material of ET (hrs) Example 14 Compound 4 152 Example 15 Compound 16 220 Comparative Example 2 ET1 179 Comparative Example 3 ET2 121

TABLE-US-00015 TABLE 14 materials of ETL and lifespan of red OLED devices of Examples 16 to 18 and Comparative Example 4 Example Lifespan (T90) No. Material of ET (hrs) Example 16 Compound 12 402 Example 17 Compound 16 505 Example 18 Compound 19 505 Comparative Example 4 ET2 347

[0119] As shown in Tables 12 to 14, adopting the novel compounds of the present invention as the electron transport material can effectively prolong lifespan of the blue, green, or red OLEDs.

[0120] 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.