Compound and organic electronic device using 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 X.sup.1 and X.sup.2 are each independently C(R.sup.a), the two (R.sup.a)s are the same or different, and the two (R.sup.a)s are joined together to form an aryl ring; X.sup.3 and X.sup.4 are each independently C(R.sup.b), the two (R.sup.b)s are the same or different, and the two (R.sup.b)s are joined together to form a heteroaryl ring containing at least one furan group or at least one thiophene group.

Claims

1. A compound represented by the following Formula (I): ##STR00199## wherein X.sup.1 and X.sup.2 are each independently C(R.sup.a), the two (R.sup.a)s are the same or different, and the two (R.sup.a)s are joined together to form an aryl ring; wherein X.sup.3 and X.sup.4 are each independently C(R.sup.b), the two (R.sup.b)s are the same or different, and the two (R.sup.b)s are joined together to form a heteroaryl ring containing at least one furan group, or at least one thiophene group; wherein at least one of Z.sup.1 to Z.sup.8 in Formula (I) is selected from the group consisting of: ##STR00200## ##STR00201## ##STR00202## ##STR00203## ##STR00204## wherein R.sup.1 to R.sup.7 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, a trifluoromethyl group, a halogen group, a cyano group, a nitro group, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 30 ring carbon atoms, a heterocycloalkyl group having 3 to 30 ring carbon atoms, an aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 3 to 20 ring carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 30 ring carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylboron group having 6 to 30 ring carbon atoms, a phosphine group having 1 to 30 carbon atoms, and a phosphine oxide group having 1 to 30 carbon atoms; wherein n is a positive integer from 0 to 4, m is a positive integer from 0 to 3, o is a positive integer from 0 to 3, and the total of m and o is not more than 5; the other(s) of Z.sup.1 to Z.sup.8, Z.sup.9 and Z.sup.10 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, a trifluoromethyl group, a halogen group, a cyano group, a nitro group, an alkyl group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an alkynyl group having 2 to 40 carbon atoms, a cycloalkyl group having 3 to 60 ring carbon atoms, a heterocycloalkyl group having 3 to 60 ring carbon atoms, an aryl group having 6 to 60 ring carbon atoms, a heteroaryl group having 3 to 60 ring carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 60 ring carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 ring carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylboron group having 6 to 60 ring carbon atoms, a phosphine group having 1 to 40 carbon atoms, and a phosphine oxide group having 1 to 40 carbon atoms.

2. The compound as claimed in claim 1, wherein the compound is represented by ##STR00205## ##STR00206## ##STR00207## wherein A.sup.1 and A.sup.2 are each independently C(R.sup.c), the two (R.sup.c)s are the same or different, and the two (R.sup.c)s are joined together to form an aromatic structure contained in the heteroaryl ring.

3. The compound as claimed in claim 2, wherein the aromatic structure contained in the heteroaryl ring is a substituted or unsubstituted 6 to 20-membered carbon aromatic cyclic structure.

4. The compound as claimed in claim 3, wherein the substituted or unsubstituted 6 to 20-membered carbon aromatic cyclic structure is selected from the group consisting of: a substituted or unsubstituted benzene structure, a substituted or unsubstituted naphthalene structure, a substituted or unsubstituted anthracene structure, a substituted or unsubstituted phenanthrene structure, a substituted or unsubstituted fluorene structure, a substituted or unsubstituted pyrene structure, a substituted or unsubstituted benzophenanthrene structure, a substituted or unsubstituted benzopyrene structure, a substituted or unsubstituted fluoranthene structure, and a substituted or unsubstituted benzofluoranthene structure.

5. The compound as claimed in claim 1, wherein the aryl ring is a substituted or unsubstituted 6 to 60-membered carbon ring.

6. The compound as claimed in claim 5, wherein the substituted or unsubstituted 6 to 60-membered carbon ring is selected from the group consisting of: a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted pyrene ring, a substituted or unsubstituted benzophenanthrene ring, a substituted or unsubstituted benzopyrene ring, a substituted or unsubstituted fluoranthene ring, and a substituted or unsubstituted benzofluoranthene ring.

7. The compound as claimed in claim 6, wherein the substituted or unsubstituted 6 to 60-membered carbon ring is a substituted or unsubstituted benzene structure.

8. The compound as claimed in claim 1, wherein at least one of Z.sup.2, Z.sup.3, Z.sup.6, and Z.sup.7 in Formula (I) is selected from the group consisting of: ##STR00208## ##STR00209## ##STR00210## ##STR00211## ##STR00212## wherein R.sup.1 to R.sup.7 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, a trifluoromethyl group, a halogen group, a cyano group, a nitro group, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 30 ring carbon atoms, a heterocycloalkyl group having 3 to 30 ring carbon atoms, an aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 3 to 20 ring carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 30 ring carbon atoms, an alkylboron group having 1 to 40 carbon atoms, an arylboron group having 6 to 30 ring carbon atoms, a phosphine group having 1 to 30 carbon atoms, and a phosphine oxide group having 1 to 30 carbon atoms; wherein n is a positive integer from 0 to 4, m is a positive integer from 0 to 3, o is a positive integer from 0 to 3, and the total of m and o is not more than 5; wherein Z.sup.1, Z.sup.4, Z.sup.5, Z.sup.8 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, a halogen group, a cyano group, a nitro group, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, and an alkynyl group having 2 to 12 carbon atoms.

9. The compound as claimed in claim 8, wherein at least one of Z.sup.2, Z.sup.3, Z.sup.6, and Z.sup.7 in Formula (I) is selected from the group consisting of: ##STR00213## ##STR00214## ##STR00215## ##STR00216## ##STR00217##

10. The compound as claimed in claim 1, wherein Z.sup.9 and Z.sup.10 in Formula (I) are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, a halogen group, a cyano group, a nitro group, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, and an alkynyl group having 2 to 12 carbon atoms.

11. The compound as claimed in claim 1, wherein the compound is selected from the group consisting of: ##STR00218## ##STR00219## ##STR00220## ##STR00221##

12. 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.

13. The organic electronic device as claimed in claim 12, wherein the organic electronic device is an organic light emitting device.

14. The organic electronic device as claimed in claim 13, 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.

15. The organic electronic device as claimed in claim 13, 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.

16. The organic electronic device as claimed in claim 12, wherein the compound is selected from the group consisting of: ##STR00222## ##STR00223## ##STR00224## ##STR00225##

Description

BRIEF DESCRIPTION OF THE DRAWINGS

(1) FIG. 1 illustrates a schematic cross-sectional view of an OLED.

(2) FIGS. 2 to 18 are respectively .sup.1H nuclear magnetic resonance (NMR) spectra of Compounds I to XVII.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

(3) 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

(4) 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.

(5) ##STR00073##

(6) Step 1: synthesis of Intermediate A1-1

(7) 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) (5 times of starting materials) was heated to about 65 C. to 70 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 solid products were obtained in a yield of 92.3%.

(8) 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.

(9) Step 2: Synthesis of Intermediate A1

(10) Intermediate A1-1 (1.0 eq) in dimethyl sulfoxide (DMSO) (w/v=1/3 to the reactants) was heated to 70 C. The reaction was monitored by HPLC. After completion of the reaction, the reaction mixture was quenched with ice water. The precipitate was separated by filtration and then purified by column chromatography on silica gel. Intermediate A1 was obtained as pale yellow solid in 93% yield.

(11) The pale yellow solid product was identified as Intermediate A1 by FD-MS analysis. FD-MS analysis C.sub.15H.sub.9BrO: theoretical value 285.14, observed value 285.14.

Synthesis of Intermediate A2

(12) Intermediate A2 used for preparing a novel compound was synthesized in a similar manner as Intermediate A1 through steps 1 and 2, 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.

(13) ##STR00074##

Synthesis of Intermediate A3

(14) Intermediate A3 used for preparing a novel compound was synthesized in a similar manner as Intermediate A1 through steps 1 and 2, 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.

(15) ##STR00075##

(16) TABLE-US-00001 TABLE 1 chemical structures, yields, formulae, and mass (M.sup.+) analyzed by FD-MS of intermediates. Intermediate A1-1 A1 Chemical Structure Yield 92.3% 93% Formula C.sub.15H.sub.9Br.sub.3O C.sub.15H.sub.9BrO Mass (M.sup.+) 444.94 285.14 Intermediate A2-1 A2 Chemical Structure Yield 91.5% 87% Formula C.sub.15H.sub.9Br.sub.3O C.sub.15H.sub.9BrO Mass (M.sup.+) 444.94 285.14 Intermediate A3-1 A3 Chemical Structure 0 Yield 93.7% 90% Formula C.sub.15H.sub.8Br.sub.4O C.sub.15H.sub.8Br.sub.2O Mass (M.sup.+) 523.84 364.03

(17) Modifications of Intermediates A1 to A3

(18) 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 Scheme A1 to A3. Applicable modifications of Intermediates A1 to A3 may be, for example, but not limited to, Intermediates A4 to A15 as follows.

(19) ##STR00082## ##STR00083##

Synthesis of Intermediates B1 to B6

(20) Intermediates B1 to B6 were synthesized by reacting 1-bromo-2-iodobenzene and heteroaryl boronic acid (Reactant An). A general synthesis pathway for Intermediate Bn was summarized in Scheme B. In the following Scheme B, Reactant An may be any one of Reactants A1 to A6 as listed in Table 2 or the like, and Intermediate Bn may be any one of Intermediates B1 to B6 as listed in Table 2.

(21) ##STR00084##

(22) According to the Scheme B, each of Intermediates B1 to B6 was synthesized by the steps as follows.

(23) 1-bromo-2-iodobenzene (1.0 eq), Reactant An (1.2 eq), potassium carbonate (3.0 eq), 200 ml of toluene, PPh.sub.3 (0.06 eq) and Pd(OAc).sub.2 (0.015 eq) were mixed and stirred at 80 C. After reaction was completed, the reaction mixture was allowed to be cooled to room temperature, and an organic layer was extracted with saturated aqueous solution of sodium chloride and EA and dried over magnesium sulfate, followed by filtering with silica gel. After a solid prepared by concentrating the filtrate under reduced pressure was suspended in hexane, the suspension was filtered again and washed with hexane to obtain Intermediate Bn. All intermediate Bn, including Intermediates B1 to B6, were analyzed according to the methods as described above, and the results were listed in Table 2.

(24) TABLE-US-00002 TABLE 2 Reactant An used for preparing Intermediates B1 to B6, and the chemical structures, yields, formulae, and mass analyzed by FD-MS of Intermediates B1 to B6. Intermediate Bn Reactant An Formula/ Chemical Structure Chemical Structure Yield Mass (M.sup.+) 87% C.sub.18H.sub.11BrO/ 323.18 88% C.sub.18H.sub.11BrO/ 323.18 0 80% C.sub.18H.sub.11BrO/ 323.18 85% C.sub.18H.sub.11BrO/ 323.18 84% C.sub.18H.sub.11BrS/ 339.25 88% C.sub.18H.sub.11BrS/ 339.25

(25) Modifications of Intermediates B1 to B6

(26) In addition to the Intermediates B1 to B6, one person skilled in the art can adopt any dihalobenzenes other than 1-bromo-2-iodobenzene and any heteroaryl boronic acids other than Reactants A1 to A6 to successfully synthesize other desired Intermediate Bn through a reaction mechanism similar to Scheme B. Applicable modifications of Intermediates B1 to B6 may be, for example, but not limited to, Intermediates B7 and B8 as follows.

(27) ##STR00097##

Synthesis of Intermediate Cn

(28) The foresaid Intermediates B1 to B8, especially Intermediates B1 to B6, could be further adopted to synthesize Intermediate Cn. A general synthesis pathway for Intermediate Cn was summarized in Scheme C1. In the following Scheme C1, Intermediate An may be any one of foresaid Intermediates A1 to A15 or the like, Intermediate Bn may be any one of foresaid Intermediates B1 to B8 or the like, and Intermediate Cn may be any one of Intermediates C1 to C9 as listed in Table 3-1 or the like. Intermediates C1 to C9 were each synthesized by the following steps.

(29) ##STR00098##

(30) Step 1: Synthesis of Intermediate Cn-1

(31) Intermediate Bn (1.0 eq) was dissolved in 120 mL of anhydrous THF (0.4M), and cooled to 78 C. n-Butyllithium (n-BuLi) (2.5 M, 1.0 eq) was slowly added to the above cooled solution, and reaction mass was stirred for 1 h. After 1 h of stirring, Intermediate An (0.7 eq) was added to the reaction solution and stirred for additional 3 h at 25 C. After completion of the reaction, it was quenched by saturated solution of ammonium chloride, and extracted with organic solvent. The organic layer was separated, concentrated, and recrystallized with petroleum ether to obtain a white solid product. The white solid product was identified as Intermediate Cn-1 by FD-MS analysis. Take Intermediate C1-1 as an example, FD-MS analysis: C.sub.33H.sub.21BrO.sub.2: theoretical value 529.42 and observed value 529.42.

(32) Intermediate Cn-1 could be directly used in step 2 without further purification. Each Intermediate Cn-1 synthesized by reacting different Intermediate An with Intermediate Bn was identified by FD-MS. The chemical structure of each Intermediate Cn-1 was listed in Table 3-1.

(33) Step 2: Synthesis of Intermediate Cn

(34) Intermediate Cn-1 (1.0 eq), acetic acid (w/v=1/3 to the reactants) and H.sub.2SO.sub.4(5 drops) were mixed, and the mixture was stirred at 110 C. for 6 h. The solvent was then removed under reduced pressure, and the residue was purified with column chromatography. The residual mass was recrystallized with toluene to obtain a white solid product.

(35) The solid product was identified by FD-MS analysis. The chemical structures, yields, formulae, and mass analyzed by FD-MS of Intermediates C1 to C9 were listed in Table 3-1.

(36) TABLE-US-00003 TABLE 3-1 Intermediate An and Bn used for preparing Intermediates Cn-1, chemical structures of Intermediates Cn-1, and chemical structures of Intermediates Cn, yields, formulae, and mass analyzed by FD-MS of Intermediates C1 to C9. Intermediate Cn Inter- Inter- Intermediate Cn-1 Chemical Structure/ mediate mediate Yield Formula/ Yield An Bn Chemical Structure (%) Mass (M.sup.+) (%) A1 B1 86 00 95 A2 B1 01 88 02 91 A3 B1 03 76 04 81 A1 B2 05 78 06 87 A1 B3 07 85 08 80 A1 B4 09 83 0 95 A1 B5 78 93 A2 B5 88 85 A1 B6 75 88

(37) Modifications of Intermediates C1 to C9

(38) In addition to the Intermediates C1 to C9, one person skilled in the art can adopt any intermediate An other than Intermediates A1 to A3 and any Intermediate Bn other than Intermediates B1 to B6 to successfully synthesize other desired Intermediate Cn through a reaction mechanism similar to Scheme C1. Applicable modifications of Intermediates C1 to C9 may be, for example, but not limited to, Intermediates C10 to C26 as follows.

(39) ##STR00117## ##STR00118## ##STR00119## ##STR00120##

Synthesis of Intermediate Cn-B

(40) The foresaid Intermediate Cn could be further modified into an Intermediate Cn-B through Miyaura borylation reaction. Intermediate Cn-B was directed to a compound derived from Intermediate Cn whose bromo group was replaced by (pinacolato)boron group. A synthesis pathway of Intermediate Cn-B was summarized in Scheme C1-B. Intermediate Cn-B was synthesized by the following steps.

(41) ##STR00121##

(42) A mixture of bis(pinacolato)diboron (1.2 eq), Intermediate Cn (1.0 eq), 1,1-bis(diphenylphosphino)-ferrocene dichloropalladium (II) (PdCl.sub.2(dppf)) (0.015 eq), and potassium acetate (KOAc) (3.0 eq) in anhydrous 1,4-dioxane (0.3 M) was stirred at 110 C. for 8 hours under nitrogen atmosphere. After cooling to room temperature, the solvent was then removed under reduced pressure, and the residue was purified via column chromatography to obtain a pale yellow solid product.

(43) The pale yellow solid product was identified by FD-MS analysis. The chemical structures, yields, formulae, and mass analyzed by FD-MS of Intermediates Cn-B were listed in Table 3-2.

(44) TABLE-US-00004 TABLE 3-2 Intermediate Cn used for preparing Intermediate Cn-B and chemical structures, yields, formulae, and mass analyzed by FD-MS of Intermediates Cn-B. Intermediate Cn Intermediate Cn-B Yield Yield Formula/ Chemical Structure (%) Chemical Structure (%) Mass (M.sup.+) 95 98 C.sub.39H.sub.31BO.sub.3/ 558.47 91 98 C.sub.39H.sub.31BO.sub.3/ 558.47 87 93 C.sub.39H.sub.31BO.sub.3/ 558.47 80 90 C.sub.39H.sub.31BO.sub.3/ 558.47 0 95 90 C.sub.39H.sub.31BO.sub.3/ 558.47 93 91 C.sub.39H.sub.31BO.sub.2S/ 574.54 85 91 C.sub.39H.sub.31BO.sub.2S/ 574.54 88 92 C.sub.39H.sub.31BO.sub.2S/ 574.54

(45) Modifications of Intermediate Cn-B

(46) In addition to the Intermediate Cn-B, one person skilled in the art can adopt any one of foresaid Intermediates Cn to undergo a Miyaura borylation reaction to successfully synthesize other desired intermediate as follows.

(47) ##STR00138##

(48) Synthesis of Novel Compounds

(49) Each of the foresaid Intermediates Cn and Cn-B could be reacted with various reactants to synthesize various claimed novel compounds. The general synthesis pathway of the claimed novel compound was summarized in Scheme I. In the following Scheme I, Reactant B may be any one of Reactants B1 to B25 as listed in Table 4, and Intermediate C may be any one of the foresaid Intermediates Cn and Cn-B or the like. The compounds were each synthesized by the following steps.

(50) ##STR00139##

(51) TABLE-US-00005 TABLE 4 chemical structure and CAS No. of Reactants B1 to B25. Reactant No. Reactant B1 Reactant B2 Reactant B3 Reactant B4 Chemical Structure 0 CAS No. [126747-14-6] [329214-79-1] [1260106-29-3] [916653-46-8] Reactant No. Reactant B5 Reactant B6 Reactant B7 Reactant B8 Chemical Structure CAS No. [29874-83-7] [29509-91-9] [3842-55-5] [952514-79-3] Reactant No. Reactant B9 Reactant B10 Reactant B11 Reactant B12 Chemical Structure 0 CAS No. [1588407-97-9] [1300115-09-6] [150255-96-2] [406482-73-3] Reactant No. Reactant B13 Reactant B14 Reactant B15 Reactant B16 Chemical Structure CAS No. [181219-01-2] [1319255-85-0] [6484-25-9] [3114-52-1] Reactant No. Reactant B17 Reactant B18 Reactant B19 Reactant B20 Chemical Structure CAS No. [867044-33-5] [7089-68-1] [1616231-57-2] [1421599-34-9] Reactant No. Reactant B21 Reactant B22 Reactant B23 Reactant B24 Chemical Structure 0 CAS No. [99682-89-0] Reactant No. Reactant B25 Chemical Structure

(52) A mixture of Intermediate C (1.0 eq), Pd(OAc).sub.2 (0.01 eq), P(Cy).sub.2(2-biphenyl) (0.04 eq), toluene/ethanol (0.5M, v/v=10/1), 3.0 M potassium carbonate solution, and Reactant Bn (2.1 eq) was stirred at 100 C. for 12 h under nitrogen atmosphere. After the completion of the reaction, water and toluene were added to the reaction mass. 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 white solid as the claimed novel compound.

(53) Reactant Bn and Intermediate C adopted to synthesize Compounds I to XVII were listed in Table 5. Compounds I to XVII were identified by H.sup.1-NMR and FD-MS, and the chemical structure, yield, formula and mass of each of Compounds I to XVII were also listed in Table 5. According to FIGS. 2 to 18 and the results of FD-MS, the chemical structure of Compounds I to XVII were identified as follows.

(54) TABLE-US-00006 TABLE 5 reactants and intermediates adopted to prepare Compounds I to XVII and their yields, formulae, and FD-MS data. Inter- Claimed Compound mediate Reactant Chemical Structure of Yield Formula/ No. No. Claimed Compound (%) Mass (M.sup.+) C1-B B7 90 C.sub.48H.sub.29N.sub.3O/ 663.76 C1 B1 95 C.sub.40H.sub.23NO/ 553.62 C1 B8 82 C.sub.52H.sub.32N.sub.2O/ 700.82 C1-B B4 75 C.sub.45H.sub.26N.sub.2O/ 610.70 C2-B B9 85 C.sub.49H.sub.28F.sub.2N.sub.2O/ 698.76 C3 B1 0 77 C.sub.47H.sub.26N.sub.2O/ 634.72 C6-B B7 90 C.sub.48H.sub.29N.sub.3O/ 663.76 C6 B1 70 C.sub.40H.sub.23NO/ 533.62 C6-B B10 82 C.sub.48H.sub.19D.sub.10N.sub.3O/ 673.83 C4-B B7 66 C.sub.48H.sub.29N.sub.3O/ 663.76 C5-B B7 87 C.sub.48H.sub.29N.sub.3O/ 663.76 C7 B3 66 C.sub.43H.sub.26N.sub.2S/ 602.74 C7-B B5 90 C.sub.47H.sub.28N.sub.2S/ 652.80 C7-B B6 82 C.sub.49H.sub.30N.sub.2S/ 678.84 C8-B B7 76 C.sub.48H.sub.29N.sub.3S/ 679.83 C9-B B7 0 77 C.sub.48H.sub.29N.sub.3S/ 679.83 C9 B1 78 C.sub.40H.sub.23NS/ 549.68

(55) Modifications of Compounds I to XVII

(56) In addition to the Compounds I to XVII, one person skilled in the art can react any Intermediate C, i.e., the foresaid Intermediate Cn or Cn-B, with any Reactant Bn through a reaction mechanism similar to Scheme I to synthesize other desired claimed novel compounds.

(57) Preparation of OLED Devices

(58) 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 minutes, and then transferred to a vacuum evaporator.

(59) After that, various organic materials and metal materials were sequentially deposited on the ITO substrate to obtain the OLED device of Examples 1 to 42 and Comparative Examples 1 to 6. 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 first hole transporting layer (HTL-1), a second hole transporting layer (HTL-2), a blue/green/red emission layer (BEL/GEL/REL), an electron transporting layer (ETL), an electron injection layer (EIL), and a cathode (Cthd).

(60) Herein, HAT was a material for forming HIL-1 and HIL-2; HI-D was a material for forming HIL-1; HI-2 was a material for forming HIL-1, HIL-2, and HTL-1; HT-1 and HT-2 were respectively materials for forming HTL-1 and HTL-2; novel compounds of the present invention, commercial ETs (BCP and TAZ) were materials for forming ETL; Liq was a material for forming ETD and EIL. RH-1 or RH-2/GH-1 or GH-2/BH was host material for forming REL/GEL/BEL, and RD/GD/BD-1 or BD-2 were dopants for forming REL/GEL/BEL. The main difference of the OLEDs between the Examples and Comparative Examples was that the ETL of OLED in the following comparative examples was made of BCP or TAZ but the ETL of OLED in the following examples was made of the novel compounds of the present invention listed in Table 5. The detailed chemical structures of foresaid commercial materials were listed in Table 6.

(61) TABLE-US-00007 TABLE 6 chemical structures of commercial materials for OLED devices. HAT HI-2 HT-1 HT-2 BH BD-1 BD-2 GH-1 GD 0 GH-2 RH-1 RH-2 RD Liq HI-D BCP TAZ (commercial ET) (commercial ET)

(62) Preparation of Red OLED Devices

(63) To prepare the red OLED devices, multiple organic layers were respectively deposited on the ITO substrate according to the sequence as listed in Table 7 to prepare a first red OLED device and a second red OLED device. The materials and the thicknesses of the organic layers in the red OLED devices were also listed in Table 7. The difference between the first and the second red OLED devices is the materials of HIL-1, HIL-2, HTL-1, and REL as listed in Table 7.

(64) TABLE-US-00008 TABLE 7 coating sequence, materials and thickness of the organic layers in the first and second red OLED devices. Material Coating First red Second red Sequence Layer OLED device OLED device Thickness 1 HIL-1 HAT HI-2 doped with 100 3.0 wt % of HI-D 2 HIL-2 HI-2 doped with HI-2 2100 5.0 wt % of HAT 3 HTL-1 HT-1 HI-2 100 4 HTL-2 HT-2 HT-2 100 5 REL RH-1 doped with RH-2 doped with 300 3.5 wt % of RD 3.5 wt % of RD 6 ETL Commercial ET/ Commercial ET/ 350 novel compounds novel compounds doped with 35.0 doped with 35.0 wt % of Liq wt % of Liq 7 EIL Liq Liq 15 8 Cthd Al Al 1500

(65) Preparation of Green OLED Devices

(66) To prepare the green OLED devices, multiple organic layers were respectively deposited on the ITO substrate according to the sequence as listed in Table 8 to prepare a first green OLED device and a second green OLED device. The materials and the thicknesses of the organic layers in the green OLED devices were also listed in Table 8. The difference between the first and the second green OLED devices is the materials of HIL-1, HIL-2, HTL-1, and GEL as listed in Table 8.

(67) TABLE-US-00009 TABLE 8 coating sequence, materials and thickness of the layers in the first and second green OLED devices. Material Coating First green Second green Sequence Layer OLED device OLED device Thickness 1 HIL-1 HAT HI-2 doped with 100 3.0 wt % of HI-D 2 HIL-2 HI-2 doped with HI-2 1300 5.0 wt % of HAT 3 HTL-1 HT-1 HI-2 100 4 HTL-2 HT-2 HT-2 100 5 GEL GH-1 doped with GH-2 doped with 400 10 wt % of GD 10 wt % of GD 6 ETL Commercial ET/ Commercial ET/ 350 novel compounds novel compounds doped with 35.0 doped with 35.0 wt % of Liq wt % of Liq 7 EIL Liq Liq 15 8 Cthd Al Al 1500

(68) Preparation of Blue OLED Devices

(69) To prepare the blue OLED devices, multiple organic layers were respectively deposited on the ITO substrate according to the sequence as listed in Table 9 to prepare a first blue OLED device and a second blue OLED device. The materials and the thicknesses of the organic layers in the blue OLED devices were also listed in Table 9. For the blue OLEDs, the dopant could be BD-1 or BD-2 as listed in Table 9. The difference between the first and the second blue OLED devices is the materials of HIL-1, HIL-2, HTL-1, and BEL as listed in Table 9.

(70) TABLE-US-00010 TABLE 9 coating sequence, materials and thickness of the layers in the first and second blue OLED devices. Material Coating First blue Second blue Sequence Layer OLED device OLED device Thickness 1 HIL-1 HAT HI-2 doped with 100 3.0 wt % of HI-D 2 HIL-2 HI-2 doped with HI-2 750 5.0 wt % of HAT 3 HTL-1 HT-1 HI-2 100 4 HTL-2 HT-2 HT-2 100 5 BEL BH doped with BH doped with 300 3.5 wt % of BD1 3.5 wt % of BD2 6 ETL Commercial ET/ Commercial ET/ 350 novel compounds novel compounds doped with 35.0 doped with 35.0 wt % of Liq wt % of Liq 7 EIL Liq Liq 15 8 Cthd Al Al 1500

(71) Performance of OLED Devices

(72) 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 10. For the blue and red OLED devices, the data were collected at 1000 nits. For the green OLED devices, the data were collected at 3000 nits.

(73) The materials of ETL, color and data of CIE, driving voltage, and current efficiency of Examples 1 to 42 and Comparative Example 1 to 4 were listed in Table 10. As listed in Table 10, the first blue OLED devices were named as B1, and the second blue OLED devices were named as B2. Similarly, the first and second red OLED devices and the first and second green OLED devices were respectively named as R1, R2, G1, and G2.

(74) TABLE-US-00011 TABLE 10 materials of ETL, colors, CIEs, voltages, and current efficiencies of OLED devices of Examples 1 to 42 and Comparative Example 1 to 6. Current Exam- OLED Effi- ple Material device Voltage ciency No. of ETL No. CIE(x, y) (V) (cd/A) E1 Compound II B1 (0.137, 0.197) 3.83 10.5 E2 Compound VI B1 (0.135, 0.18) 4.55 9.2 E3 Compound VIII B1 (0.136, 0.176) 3.97 9.66 E4 Compound I B2 (0.129, 0.157) 4.7 7.81 E5 Compound III B2 (0.129, 0.157) 5.16 7.45 E6 Compound IV B2 (0.130, 0.152) 4.31 8.31 E7 Compound VII B2 (0.130, 0.150) 4.44 7.73 E8 Compound IX B2 (0.129, 0.17) 4.62 8.3 E9 Compound X B2 (0.129, 0.161) 4.43 8.08 E10 Compound XI B2 (0.130, 0.153) 4.49 7.94 E11 Compound XII B2 (0.130, 0.163) 4.44 8.99 E12 Compound XIII B2 (0.129, 0.161) 4.86 7.45 E13 Compound XIV B2 (0.130, 0.164) 4.1 10.4 E14 Compound XV B2 (0.129, 0.158) 4.45 10 E15 Compound XVI B2 (0.129, 0.156) 4.79 7.86 E16 Compound XVII B2 (0.138, 0.181) 3.88 12.2 C1 BCP B1 (0.130, 0.170) 6.35 7.05 C2 TAZ B2 (0.131, 0.174) 7.84 6.55 E17 Compound II G1 (0.309, 0.641) 3.06 66.0 E18 Compound VI G1 (0.307, 0.642) 3.24 70.3 E19 Compound VIII G1 (0.322, 0.635) 3.33 77.6 E20 Compound I G2 (0.313, 0.639) 4.21 71.4 E21 Compound III G2 (0.312, 0.639) 5.05 57.5 E22 Compound IV G2 (0.322, 0.634) 4.4 75.9 E23 Compound V G2 (0.321, 0.634) 6.17 74.1 E24 Compound VII G2 (0.319, 0.636) 4.3 78.3 E25 Compound IX G2 (0.328, 0.63) 4.25 77.4 E26 Compound X G2 (0.323, 0.633) 4.16 75.8 E27 Compound XI G2 (0.317, 0.637) 3.96 72.2 E28 Compound XII G2 (0.322, 0.635) 4.25 72 E29 Compound XIII G2 (0.324, 0.633) 4.93 58.9 E30 Compound XIV G2 (0.321, 0.634) 3.99 80.2 E31 Compound XV G2 (0.322, 0.634) 4.75 79.9 E32 Compound XVI G2 (0.323, 0.634) 4.24 76.2 E33 Compound XVII G2 (0.317, 0.638) 3.51 77.2 C3 BCP G1 (0.313, 0.638) 5.27 65.3 C4 TAZ G2 (0.325, 0.628) 8.36 48.4 E34 Compound II R1 (0.606, 0.339) 3.18 22.5 E35 Compound VI R1 (0.659, 0.339) 3.23 20.8 E36 Compound VIII R1 (0.662, 0.337) 3.43 24.9 E37 Compound IV R2 (0.659, 0.339) 4.09 28 E38 Compound IX R2 (0.658, 0.34) 3.9 29.7 E39 Compound XII R2 (0.658, 0.34) 4.55 26.8 E40 Compound XIV R2 (0.656, 0.341) 4.13 29.9 E41 Compound XV R2 (0.657, 0.341) 4.31 30.6 E42 Compound XVII R2 (0.663, 0.336) 3.91 23.3 C5 BCP R1 (0.659, 0.340) 4.16 20.10 C6 TAZ R2 (0.648, 0.342) 11.38 21.04

(75) Based on the results, in comparison with the commercial electron transport material, adopting Compounds I to XVII as the electron transport material can reduce the driving voltage and improve the current efficiency of the red, green, or blue OLEDs. It demonstrated that the novel compound of the present invention is suitable as an electron transport material for any color OLEDs, and allows the OLEDs using the same to have low driving voltage and improved current efficiency.

(76) 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.