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 A.sup.1 and A.sup.2 each represent a carbon atom; *1 is bonded to one of A.sup.1 and A.sup.2, and *2 is bonded to the other of A.sup.1 and A.sup.2; a is an integer from 1 to 4; b is an integer from 0 to 3.

Claims

1. A compound represented by the following Formula (I): ##STR00229## wherein A.sup.1 and A.sup.2 each represent a carbon atom; *1 is bonded to one of A.sup.1 and A.sup.2, and *2 is bonded to the other of A.sup.1 and A.sup.2; a is an integer from 1 to 4; b is an integer from 0 to 3; L is an arylene group having 6 to 60 carbon atoms; G is selected from the group consisting of: a heteroaryl group having 3 to 60 ring carbon atoms, an alkyl group having 1 to 40 carbon atoms and substituted with at least one functional group, an alkenyl group having 2 to 40 carbon atoms and substituted with at least one functional group, an alkynyl group having 2 to 40 carbon atoms and substituted with at least one functional group, a cycloalkyl group having 3 to 60 ring carbon atoms and substituted with at least one functional group, a heterocycloalkyl group having 3 to 60 ring carbon atoms and substituted with at least one functional group, an alkoxy group having 1 to 40 carbon atoms and substituted with at least one functional group, an aryl group having 6 to 60 ring carbon atoms and substituted with at least one functional group, an aryloxy group having 6 to 60 ring carbon atoms and substituted with at least one functional group, an alkylsilyl group having 1 to 40 carbon atoms and substituted with at least one functional group, an arylsilyl group having 6 to 60 ring carbon atoms and substituted with at least one functional group, an alkylboron group having 1 to 40 carbon atoms and substituted with at least one functional group, an arylboron group having 6 to 60 ring carbon atoms and substituted with at least one functional group, a phosphine group having 1 to 40 carbon atoms and substituted with at least one functional group, and a phosphine oxide group having 1 to 40 carbon atoms and substituted with at least one functional group, any isomeric groups thereof, and any deuterated analogs thereof, wherein the functional group is selected from the group consisting of: a cyano group, a nitro group, a trifluoromethyl group, a fluoro group, and a chloro group; c is an integer from 0 to 4; Y is selected from the group consisting of: a deuterium atom, an unsubstituted aryl group having 6 to 60 ring carbon atoms, an unsubstituted alkyl group having 1 to 12 carbon atoms, an unsubstituted alkenyl group having 2 to 12 carbon atoms, and an unsubstituted alkynyl group having 2 to 12 carbon atoms; and Z.sup.1 and Z.sup.2 are each independently an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms, and Z.sup.1 and Z.sup.2 are the same or different.

2. The compound as claimed in claim 1, wherein a in Formula (I) is the integer 1.

3. The compound as claimed in claim 1, wherein the compound is represented by any one of the following formulae: ##STR00230## ##STR00231##

4. The compound as claimed in claim 1, wherein the heteroaryl group having 3 to 60 ring carbon atoms represented by G in Formula (I) is selected from the group consisting of: a furyl group, a pyrrolyl group, a thiophenyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group; a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group; an indolyl group, an isoindolyl group, a benzofuranyl group, an isobenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, an indolizinyl group, a quinolizinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, an indazolyl group, a benzisoxazolyl group, a benzisothiazolyl group; a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a biscarbazolyl group, a coumarinyl group, a chromenyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a phenothiazinyl group, a phenoxazinyl group, an azatriphenylenyl group, a diazatriphenylenyl group, a xanthenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, a benzofuranobenzothiophenyl group, a benzothienobenzothiophenyl group, a dibenzofuranonaphthyl group, a dibenzothienonaphthyl group, a dinaphthothienothiophenyl group, a dinaphtho carbazolyl group, a dibenzo[b,f]azepin group, a tribenzo[b,d,f]azepin group, a dibenzo[b,f]oxepin group, a tribenzo[b,d,f]oxepin group, any isomeric groups thereof, and any deuterated analogs thereof.

5. The compound as claimed in claim 4, wherein the heteroaryl group having 3 to 60 ring carbon atoms represented by G in Formula (I) is selected from the group consisting of: a furyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, an isoindolyl group, an isobenzofuranyl group, an isobenzothiophenyl group, an indolizinyl group, a quinolizinyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, an indazolyl group, a benzisoxazolyl group, a benzisothiazolyl group, a biscarbazolyl group, a coumarinyl group, a chromenyl group, a phenanthridinyl group, an azatriphenylenyl group, a diazatriphenylenyl group, a xanthenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, a benzofuranobenzothiophenyl group, a benzothienobenzothiophenyl group, a dibenzofuranonaphthyl group, a dibenzothienonaphthyl group, a dinaphthothienothiophenyl group, a dinaphtho carbazolyl group, a dibenzo[b,f]azepin group, a tribenzo[b,d,f]azepin group, a dibenzo[b,f]oxepin group, a tribenzo[b,d,f]oxepin group, any isomeric groups thereof, and any deuterated analogs thereof.

6. The compound as claimed in claim 1, wherein G in Formula (I) is selected from the group consisting of: ##STR00232## ##STR00233## ##STR00234## ##STR00235## ##STR00236## ##STR00237## ##STR00238## ##STR00239## ##STR00240## ##STR00241## ##STR00242## wherein o is an integer from 0 to 2; m is an integer from 0 to 3; n is an integer from 0 to 4; and p is an integer from 0 to 5; wherein R.sup.1 to R.sup.5 are each independently selected from the group consisting of: a deuterium atom, a halogen group, a cyano group, a nitro group, a trifluoromethyl 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 carbon atoms, a heterocycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylboron group having 1 to 30 carbon atoms, an arylboron group having 6 to 30 carbon atoms, a phosphine group having 1 to 30 carbon atoms, and a phosphine oxide group having 1 to 30 carbon atoms.

7. The compound as claimed in claim 6, wherein G in Formula (I) is selected from the group consisting of: ##STR00243## ##STR00244## ##STR00245## ##STR00246## ##STR00247## ##STR00248## ##STR00249## ##STR00250## ##STR00251##

8. The compound as claimed in claim 1, wherein the aryl group having 6 to 60 ring carbon atoms and substituted with at least one functional group represented by G in Formula (I) is selected from the group consisting of: a phenyl group substituted with the at least one functional group, a biphenyl group substituted with the at least one functional group, a terphenyl group substituted with the at least one functional group, a naphthyl group substituted with the at least one functional group, a phenanthryl group substituted with the at least one functional group, an anthracenyl group substituted with the at least one functional group, a benzanthryl group substituted with the at least one functional group, a fluorenyl group substituted with the at least one functional group, a chrysenyl group substituted with the at least one functional group, a fluoranthenyl group substituted with the at least one functional group, and any deuterated analogs thereof.

9. The compound as claimed in claim 1, wherein the aryl group having 6 to 60 ring carbon atoms and substituted with at least one functional group represented by G in Formula (I) is selected from the group consisting of: ##STR00252## wherein r is an integer from 1 to 5; s is an integer from 0 to 4; and the sum of r and s is not more than 5; wherein R.sup.1 is selected from the group consisting of: a deuterium atom, 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 30 ring carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an alkylsilyl group having 1 to 12 carbon atoms, an arylsilyl group having 6 to 30 ring carbon atoms, an alkylboron group having 1 to 12 carbon atoms and an arylboron group having 6 to 30 ring carbon atoms.

10. The compound as claimed in claim 1, wherein Y is selected from the group consisting of: a deuterium atom, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, an anthracenyl group, a benzanthryl group, a fluorenyl group, a chrysenyl group, a fluoranthenyl group, a deuterated phenyl group, a deuterated biphenyl group, a deuterated terphenyl group, a deuterated naphthyl group, a deuterated phenanthryl group, a deuterated anthracenyl group, a deuterated benzanthryl group, a deuterated fluorenyl group, a deuterated chrysenyl group, and a deuterated fluoranthenyl group.

11. The compound as claimed in claim 1, wherein b is the integer 0.

12. The compound as claimed in claim 1, wherein b is an integer of 1 to 3, and L is selected from the group consisting of: ##STR00253##

13. The compound as claimed in claim 1, wherein the group [(L).sub.b-G] is selected from the group consisting of: ##STR00254## ##STR00255## ##STR00256## ##STR00257## ##STR00258## ##STR00259## ##STR00260## ##STR00261## ##STR00262## ##STR00263## ##STR00264## ##STR00265## ##STR00266## ##STR00267## ##STR00268## ##STR00269## ##STR00270## ##STR00271## ##STR00272## ##STR00273## ##STR00274## ##STR00275## ##STR00276## ##STR00277## ##STR00278## ##STR00279## ##STR00280## ##STR00281## ##STR00282## ##STR00283## ##STR00284## ##STR00285## ##STR00286## ##STR00287## ##STR00288## ##STR00289## ##STR00290## ##STR00291## ##STR00292## ##STR00293## ##STR00294## ##STR00295## ##STR00296## ##STR00297## ##STR00298## ##STR00299## ##STR00300## ##STR00301## ##STR00302## ##STR00303## ##STR00304## ##STR00305## ##STR00306## ##STR00307## ##STR00308## ##STR00309## ##STR00310## ##STR00311## ##STR00312## ##STR00313## ##STR00314## ##STR00315## ##STR00316## ##STR00317## ##STR00318##

14. The compound as claimed in claim 12, wherein L is ##STR00319##

15. The compound as claimed in claim 1, wherein the compound is selected from the group consisting of: ##STR00320## ##STR00321## ##STR00322## ##STR00323## ##STR00324##

16. 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.

17. The organic electronic device as claimed in claim 16, wherein the organic electronic device is an organic light emitting device.

18. The organic electronic device as claimed in claim 17, 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.

19. The organic electronic device as claimed in claim 17, 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.

20. The organic electronic device as claimed in claim 16, wherein the compound is selected from the group consisting of: ##STR00325## ##STR00326## ##STR00327## ##STR00328## ##STR00329##

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0073] FIG. 1 illustrates a schematic cross-sectional view of an OLED;

[0074] FIGS. 2 to 19 respectively are .sup.1H nuclear magnetic resonance (NMR) spectra of compounds 1 to 18.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT

[0075] 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.

Pathway 1: Synthesis of Intermediate An

[0076] Intermediate An used for preparing a novel compound was synthesized by the following steps. The synthesis pathway of Intermediate An was summarized in Scheme A1.

##STR00125##

[0077] Where in B is B(OH).sub.2 group or

##STR00126##

group.

Synthesis of Intermediate A1

[0078] Taking Intermediate A1 as an example of Intermediate An which is synthesized by Scheme A1, the synthesis pathway of Intermediate A1 was summarized in Scheme A1-1.

##STR00127##

Step 1: Synthesis of Intermediate A1-1

[0079] 9,9-Dimethylfluorene-2-boronic acid (CAS No. 333432-28-3) as Reactant R.1 (1.2eq), Reactant 131 (1.0eq), palladium(11) acetate [Pd(OAc).sub.2] (0.015eq), triphenylphosphine (PPh.sub.3) (0.06eq), and potassium carbonate (K.sub.2CO.sub.3) (3.0M, 1.5eq) were mixed in 200 ml of toluene, and the reaction mixture was heated to about 80 C. and stirred. After completion of the reaction, the reaction mixture was cooled to room temperature, and the crude product was extracted with saturated aqueous solution of sodium chloride and ethyl acetate (EA) and collected by the organic layer. The organic layer was dried over magnesium sulfate (MgSO.sub.4), separated by filtration with silica gel and concentrated under reduced pressure. A resulting residue was suspended in hexane, and the suspension was then filtered again and washed with hexane to obtain Intermediate A1-1. Intermediate A1-1 could be directly used in step 2 without further purification.

Step 2: Synthesis of Intermediate A1-2

[0080] Intermediate A1-1 (1.0eq) and tetra-n-butylammonium fluoride (TBAF) (1.5eq) were dissolved in tetrahydrofuran (THF) (0.3M) and stirred at room temperature for 1 hour. The solvent was then removed under reduced pressure, and the residue was purified with column chromatography to get a white solid product. The yield of step 2 was 79%.

[0081] The white solid product was identified as Intermediate A1-2 by a field desorption mass spectroscopy (FD-MS) analysis. The chemical structure was listed in Table 1.

Step 3: Synthesis of Intermediate A1-3

[0082] Cesium hydroxide hydrate (CsOH*H.sub.2O)(0.3 eq) were dissolved in N-methyl-2-pyrrolidone (NMP)(0.3M) and stirred at room temperature for 10 minutes. The solution was then added Maki (1.7 eq) and intermediate A1-2, and the mixture were stirred and heated at 110 C. for 6 hrs. The solvent was then removed under reduced pressure, and the residue was purified with column chromatography by using Toluene/Hexane (2/1) to get oil type product. The yield of step 3 was 85%.

Step 4: Synthesis of Intermediate A1

[0083] Intermediate A1-3 (1 eq) was dissolved in dichloromethane (CH.sub.2Cl.sub.2)(0.3 M) and cooled to 0 C. Then the solution was added CF.sub.3SO.sub.3H (0.2 eq) slowly drop by drop and stirred for 2 hrs at 0 C. After completion of the reaction, the solvent was quenched by NaHCO.sub.3(aq), then removed the water layer. The solvent contained in the organic layer was removed under reduced pressure, and the residue was purified with column chromatography to obtain a white solid product. The yield of step 4 was 85%.

[0084] The white solid product was identified as Intermediate A1 by a FD-MS analysis. FD-MS analysis: C.sub.23H.sub.17Cl: theoretical value 328.83 and observed value 328.83. The chemical structure was listed in Table 1.

[0085] Syntheses of Intermediates A2 and A3

[0086] Intermediates A2 and A3, which also can be used for preparing a novel compound, were respectively synthesized in a similar manner as Intermediate A1 through steps 1 to 4, except that the starting material Reactant B1 was replaced with Reactants B2 and B3, respectively. All intermediates were analyzed as described above, and the results were listed in Table 1.

TABLE-US-00001 TABLE 1 Reactants An and Bn used for preparing Intermediates An, chemical structures of Intermediates An-1, An-2, An-3, and An, yields of Intermediates An-2, An-3, and An, formulae, and mass analyzed by FD-MS of Intermediates A1 to A3 Reactant An No. Reactant A1 Chemical Structure/ CAS No. of Reactant Bn [00128] Reac- tant B1 [00129] Reac- tant B2 Chemical Structure of Intermediate An-1 [00130] Inter- mediate A1-1 [00131] Inter- mediate A2-1 Chemical Structure of Intermediate An-2 [00132] Inter- mediate A1-2 [00133] Inter- mediate A2-2 Yield(%) 79 81 Chemical Structure of Intermediate An-3 [00134] Inter- mediate A1-3 [00135] Inter- mediate A2-3 Yield(%) 85 82 Chemical Structure of Intermediate An [00136] Inter- mediate A1 [00137] Inter- mediate A2 Yield(%) 85 83 Formula/ C.sub.23H.sub.17Cl/ C.sub.23H.sub.17Cl/ Mass (M.sup.+) 328.83 328.83 Reactant An No. Reactant A1 Chemical Structure/ CAS No. of Reactant Bn [00138] Reac- tant B3 Chemical Structure of Intermediate An-1 [00139] Inter- mediate A3-1 Chemical Structure of Intermediate An-2 [00140] Inter- mediate A3-2 Yield(%) 66 Chemical Structure of Intermediate An-3 [00141] Inter- mediate A3-3 Yield(%) 73 Chemical Structure of Intermediate An [00142] Inter- mediate A3 Yield(%) 82 Formula/ C.sub.23H.sub.17Cl/ Mass (M.sup.+) 328.83

Modifications of Intermediates A1 to A3

[0087] In addition to Intermediates A1 to A3, one person skilled in the art can adopt other applicable starting materials and successfully synthesize other desired intermediates through a reaction mechanism similar to Scheme A1-1.

Pathway 2: Synthesis of Intermediate A4 and A5

[0088] Intermediate An used for preparing a novel compound can also be synthesized by the following steps. The synthesis pathway of Intermediate An was summarized in Scheme A2.

##STR00143##

[0089] Wherein B is B(OH).sub.2 group or

##STR00144##

group.

Synthesis of Intermediate A4

[0090] Taking Intermediate A4 as an example of Intermediate An which is synthesized by Scheme A2, the synthesis pathway of Intermediate A4 was summarized in Scheme A2-1.

##STR00145##

Step 1: Synthesis of Intermediate A4-1

[0091] 9,9-Dimethylfluorene-3-borortic acid pinacol ester (CAS No. 1346007-02-0) as Reactant R2 (1.2eq), Reactant B1 (1.0eq), Pd(OAc).sub.2 (0.015eq), PP11.sub.3 (0.06eq), and K.sub.2CO.sub.3 (3.0M, 1.5eq) were mixed in 200 ml of toluene, and the reaction mixture was heated to about 80 C. and stirred. After completion of the reaction, the reaction mixture was cooled to room temperature, and the crude product was extracted with saturated aqueous solution of sodium chloride and ethyl acetate and collected by the organic layer The organic layer was dried over MgSO.sub.4, separated by filtration with silica gel and concentrated under reduced pressure. A resulting residue was suspended in hexane, the suspension was then filtered again and washed with hexane to obtain Intermediate A4-1. Intermediate A4-1 could be directly used in step 2 without further purification.

Step 2: Synthesis of Intermediate A4-2

[0092] Intermediate A4-2 was synthesized in a similar manner as Intermediate A1-2 through step 2, except that the starting material Intermediate A1-1 was replaced by intermediate A4-1. The yield of step 2 was 70%. The chemical structure was listed in Table 2.

Step 3: Synthesis of Intermediate A4-3

[0093] Intermediate A4-3 was synthesized in a similar manner that Intermediate A1-3 was obtained through foresaid step 3, except that the starting material Intermediate A1-2 was replaced by Intermediate A4-2. The yield of step 3 was 83%.

Step 4: Synthesis of Intermediate A4

[0094] Intermediate A4 was synthesized in a similar manner as Intermediate A1 through step 4, except that the starting material Intermediate A1-3 was replaced by Intermediate A4-3. The yield of step 4 was 63%. Intermediate A4 was identified by a FD-MS analysis. FD-MS analysis: C.sub.23H.sub.17Cl: theoretical value 328.83 and observed value 328.83. The chemical structure was listed in Table 2.

Syntheses of Intermediate A5

[0095] Intermediate A5, which also can be used for preparing a novel compound, was respectively synthesized in a similar manner as Intermediate A4 through steps 1 to 4, except that the starting material Reactant B1 was replaced with Reactants B2. All intermediates were analyzed as described above, and the results were listed in Table 2.

TABLE-US-00002 TABLE 2 Reactants An and Bn used for preparing Intermediates An, chemical structures of Intermediates An-1, An-2 and An, yields of Intermediates An-2 and An, formulae, and mass analyzed by FD-MS of Intermediates A4 and A5 Reactant An No. Reactant An Chemical Structure/ CAS No. of Reactant Bn [00146] Reac- tant B1 [00147] Reac- tant B2 Chemical Structure of Intermediate An-1 [00148] Inter- mediate A4-1 [00149] Inter- mediate A5-1 Chemical Structure of Intermediate An-2 [00150] Inter- mediate A4-2 [00151] Inter- mediate A5-2 Yield(%) 75 84 Chemical Structure of Intermediate An-3 [00152] Inter- mediate A4-3 [00153] Inter- mediate A5-3 Yield(%) 83 78 Chemical Structure of Intermediate An-3 [00154] Inter- mediate A4 [00155] Inter- mediate A5 Yield(%) 63 67 Formula/ C.sub.23H.sub.17Cl/ C.sub.23H.sub.17Cl/ Mass (M.sup.+) 328.83 328.83

[0096] Modifications of Intermediates A4 and A5

[0097] In addition to Intermediates A4 and A5, one person skilled in the art can adopt other applicable starting materials and successfully synthesize other desired intermediates through a reaction mechanism similar to Scheme A2-1. Applicable modifications of Intermediate A4 and A5 may be, for example, but not limited to, Intermediate A6 as follows.

##STR00156##

Synthesis of Intermediate An-B

[0098] The general synthesis pathway of Intermediate An-B was summarized in Scheme A3.

##STR00157##

Synthesis of Intermediate A1-B

[0099] Taking Intermediate A1-B as an example of Intermediate An-B, the synthesis pathway of Intermediate A1-B was summarized in Scheme A3-1.

##STR00158##

[0100] A mixture of Intermediate A1 (1.0 eq), bis(pinacolato)diboron (1.20 eq), tris(dibenzylideneacetone)dipalladium(0)[Pd.sub.2(dba).sub.3)] (0.015 eqdicyclohexyl(2,6-dimethoxy-[1,1-biphenyl]-2-yl)phosphine(0.03 eq, SPhos) and potassium acetate (KOAc) (1.5 eq) in anhydrous 1,4-dioxane (0.5 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 with column chromatography to obtain a pale yellow solid product. The yield of step 5 was 89%.

[0101] The pale yellow solid product was identified as Intermediate A1-B by a FD-MS analysis. The chemical structure, yield, formula, and mass analyzed by FD-MS of Intermediate A1-B were listed in Table 3.

Syntheses of Intermediates A2-B to A5-B

[0102] Intermediates A2-B to A5-B, which also can be used for preparing a novel compound, were respectively synthesized in a similar manner as Intermediate A1-B through step 4, except that the starting material Intermediate A1 was replaced with Intermediate A2 to A5, respectively. All intermediates were analyzed as described above, and the results were listed in Table 3.

TABLE-US-00003 TABLE 3 Intermediates An used for preparing Intermediates An-B, chemical structures of Intermediates An and An-B, yields of Intermediates An-B, formulae, and mass analyzed by FD-MS of Intermediates An-B Intermediate An-B For- mula/ Intermediate An Yield Mass Chemical Structure Chemical Structure (%) (M.sup.+) [00159] In- ter- me- di- ate A1 [00160] In- ter- me- di- ate A1- B 89 C.sub.29H.sub.29 BO.sub.2/ 420.35 [00161] In- ter- me- di- ate A2 [00162] In- ter- me- di- ate A2- B 95 C.sub.29H.sub.29 BO.sub.2/ 420.35 [00163] In- ter- me- di- ate A3 [00164] In- ter- me- di- ate A3- B 70 C.sub.29H.sub.29 BO.sub.2/ 420.35 [00165] In- ter- me- di- ate A4 [00166] In- ter- me- di- ate A4- B 96 C.sub.29H.sub.29 BO.sub.2/ 420.35 [00167] In- ter- me- di- ate A5 [00168] In- ter- me- di- ate A5- B 83 C.sub.29H.sub.29 BO.sub.2/ 420.35

Modifications of Intermediates A1-B to A5-B

[0103] In addition to Intermediates A1-B to A5-B, one person skilled in the art can adopt other starting materials and successfully synthesize other desired intermediates through a reaction mechanism similar to Scheme A3-1.

[0104] Applicable modifications of Intermediates A1-B to A5-B may be, for example, but is not limited to, Intermediate A6-B as follows.

##STR00169##

Preparation of Reactants Dn

[0105] Reactants Dn used for preparing a novel compound were listed in Table 4. Reactants D1, D3 to D23 were purchased from Sigma-Aldrich.

TABLE-US-00004 TABLE 4 chemical structures and the CAS No. of the Reactants D1 to D23 Reactant D1 [00170] Reactant D2 [00171] Reactant D3 [00172] Reactant D4 [00173] Reactant D5 [00174] Reactant D6 [00175] Reactant D7 [00176] Reactant D8 [00177] Reactant D9 [00178] Reactant D10 [00179] Reactant D11 [00180] Reactant D12 [00181] Reactant D13 [00182] Reactant D14 [00183] Reactant D15 [00184] Reactant D16 [00185] Reactant D17 [00186] Reactant D18 [00187] Reactant D19 [00188] Reactant D20 [00189] Reactant D21 [00190] Reactant D22 [00191] Reactant D23 [00192]

Synthesis of Reactant D2

[0106] The synthesis pathway of the Reactant D2 was summarized in Scheme D2.

##STR00193##

[0107] 4-bromobenzaldehyde (CAS No. 1122-91-4) (1.0 eq) and 1-[4-(3-Pyridinyl)phenyl]ethanone (CAS No. 90395-45-2) (1.0 eq) dissolved in absolute ethanol (0.5 M) were stirred, and an aqueous solution of potassium hydroxide (KOH) (3.0 eq, 2.5 M) was added dropwise at 0 C., and then the reaction mixture was stirred at room temperature for 12 hours. After that, 4-bromobenzamidine.HCl (CAS No. 1670-14-0) (1.0 eq) was added to the foresaid reaction mixture and heated at reflux temperature for another 6 hours. After completion of the reaction, the solvent was then removed under reduced pressure, and the residue was purified with column chromatography to get a white solid product in a yield of 34%. The white solid product was identified as Reactant D2 by a FD-MS analysis. FD-MS analysis: C.sub.27H.sub.18BrN.sub.3: theoretical value 464.36 and observed value 464.36. The chemical structure was listed in Table 4.

[0108] Synthesis of Novel Compounds

[0109] Each of the foresaid Intermediates, e.g., Intermediates An and An-B could be reacted with various Reactants Dn 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, Intermediate A may be any one of the foresaid Intermediates An and An-B as listed in Tables 1 to 3 or the like, and Reactant Dn may be any one of Reactants D1 to D23 as listed in Table 4. The compounds were each synthesized by the following method I or method II, and the results were listed in Table 5.

##STR00194##

[0110] Intermediate A (1.0eq), Reactant Dn (1.2eq), Pd(OAc).sub.2 (0.01eq), and 2-(dicyclohexylphosphino)biphenyl [P(Cy).sub.2(2-biPh)] (0.04eq) were stirred in a mixed solution of toluene/ethanol(0.5M, v/v=10/1), and 3.0M of K.sub.2CO.sub.3 aqueous solution. 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.

##STR00195##

[0111] Intermediate A (1.0 eq), Reactant Dn (1.2 eq), Tris(dibenzylitteneacetone)dipalladium(0) (Pd.sub.2(dba).sub.3 (0.015eq), and Tricyclohexylphosphinte tetrafiuoroborate [P(Cy).sub.3(HB F4)](0.06eq) were stirred in a mixed solution of DME (0.5 M, v/v=10/1), and 3.0 M of K.sub.2CO.sub.3 aqueous solution. The reaction mixture was heated to about 90 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.

[0112] Intermediates A and Reactants Dn adopted to synthesize Compounds 1 to 18 were listed in Tables 5-1 and 5-2.

[0113] Compounds 1 to 18 were identified by .sup.1H-NMR and FD-MS, and the chemical structure, yield, formula and mass of each of Compounds 1 to 12 were also listed in Table 5-1 and 5-2. According to FIGS. 2 to 19 and the results of .sup.1H-NMR, the chemical structures of Compounds 1 to 18 were identified as follows.

TABLE-US-00005 TABLE 5-1 Intermediates A and Reactant Dn adopted to prepare novel compound by method I and their yields, formulae, and FD-MS data Claimed Compound Intermediate Reactant Chemical Structure of Yield Formula/ A Dn Claimed Compound (%) Mass (M.sup.+) A1-B D2 [00196] Compound 1 90 C.sub.50H.sub.35N.sub.3/ 677.83 A1 D7 [00197] Compound 3 65 C.sub.33H.sub.24N.sub.2/ 448.56 A1 D9 [00198] Compound 4 61 C.sub.33H.sub.24N.sub.2/ 448.56 A2-B D2 [00199] Compound 6 82 C.sub.50H.sub.35N.sub.3/ 677.83 A3-B D2 [00200] Compound 8 74 C.sub.50H.sub.35N.sub.3/ 677.83 A4-B D2 [00201] Compound 10 77 C.sub.50H.sub.35N.sub.3/ 677.83 A2 D23 [00202] Compound 13 85 C.sub.50H.sub.35N.sub.3/ 677.83 A1 D22 [00203] Compound 14 88 C.sub.44H.sub.31N.sub.3/ 601.74 A1 D23 [00204] Compound 15 84 C.sub.50H.sub.35N.sub.3/ 677.83 A2 D22 [00205] Compound 16 88 C.sub.44H.sub.31N.sub.3/ 601.74

TABLE-US-00006 TABLE 5-2 Intermediates A and Reactant Dn adopted to prepare novel compound by method II and their yields, formulae, and FD-MS data Claimed Compound Intermediate Reactant Chemical Structure of Yield Formula/ A Dn Claimed Compound (%) Mass (M.sup.+) A1-B D1 [00206] Compound 2 76 C.sub.50H.sub.35N.sub.3/ 677.83 A1-B D6 [00207] Compound 5 77 C.sub.50H.sub.35N.sub.3/ 677.83 A2-B D1 [00208] Compound 7 87 C.sub.50H.sub.35N.sub.3/ 677.83 A3-B D1 [00209] Compound 9 76 C.sub.50H.sub.35N.sub.3/ 677.83 A4-B D1 [00210] Compound 11 80 C.sub.50H.sub.35N.sub.3/ 677.83 A5-B D1 [00211] Compound 12 83 C.sub.50H.sub.35N.sub.3/ 677.83 A1-B D20 [00212] Compound 17 75 C.sub.44H.sub.29N.sub.3O/ 615.72 A1-B D21 [00213] Compound 18 78 C.sub.44H.sub.29N.sub.3O/ 615.72

Modifications of Compounds 1 to 18

[0114] In addition to the Compounds 1 to 18, one person skilled in the art can react any Intermediates A with any Reactants Dn through a reaction mechanism similar to Scheme I and Scheme II to synthesize other desired claimed novel compounds.

[0115] Preparation of OLED Devices

[0116] A glass substrate coated with ITO layer (abbreviated in 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.

[0117] 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 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).

[0118] Herein, HAT was a material for forming HIL-1 and HIL-2; HI-2 was a material for forming HIL-2; HT-1 and HT-2 were respectively materials for forming HTL-1 and HTL-2; novel compounds of the present invention and commercial ET (BCP) 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 main difference of the OLEDs between the Examples and Comparative Examples was that the ETL of OLED in the following comparative examples were made of BCP, TPBi, or other Comparative Compounds but the ETL of OLED in the following examples was made of the novel compounds of the present invention listed in Tables 5-1 and 5-2. The detailed chemical structures of foresaid commercial materials and other Comparative Compounds used in the OLED devices were listed in Table 6.

TABLE-US-00007 TABLE 6 chemical structures of commercial materials for OLED devices. HAT [00214] HI-2 [00215] Liq [00216] HT-1 [00217] HT-2 [00218] BCP (commercial ET) [00219] RH [00220] GH [00221] BH [00222] RD [00223] GD [00224] BD [00225] TPBi (commercial ET) [00226] Comparative Compound 1 [00227] Comparative Compound 2 [00228]

[0119] Preparation of Blue OLED Devices

[0120] To prepare the blue OLED device, multiple organic layers were respectively deposited on the ITO substrate according to the sequence as listed in Table 7, and the materials and the thicknesses of the organic layers in blue OLED devices were also listed in Table 7.

TABLE-US-00008 TABLE 7 coating sequence, materials and thickness of the layers in blue OLED device Coating Sequence Layer Material Thickness 1 HIL-1 HAT 100 2 HIL-2 HI-2 doped with 5.0 wt % of HAT 750 3 HTL-1 HT-1 100 4 HTL-2 HT-2 100 5 BEL BH doped with 3.5 wt % of BD 250 6 ETL Commercial ET/Comparative 250 Compound/Novel compounds doped with 35.0 wt % of Liq 7 EIL Liq 15 8 Cthd Al 1500

[0121] Preparation of Green OLED Devices

[0122] To prepare the green 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 green OLED devices were also listed in Table 8.

TABLE-US-00009 TABLE 8 coating sequence, materials and thickness of the layers in green OLED device Coating Sequence Layer Material Thickness 1 HIL-1 HAT 100 2 HIL-2 HI-2 doped with 5.0 wt % of HAT 1300 3 HTL-1 HT-1 100 4 HTL-2 HT-2 100 5 GEL GH doped with 10.0 wt % of GD 400 6 ETL Commercial ET/Comparative 350 Compound/Novel compounds doped with 35.0 wt % of Liq 7 EIL Liq 15 8 Cthd Al 1500

[0123] Preparation of Red OLED Devices

[0124] 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 HAT 100 2 HIL-2 HI-2 doped with 5.0 wt % of HAT 2100 3 HTL-1 HT-1 100 4 HTL-2 HT-2 100 5 REL RH doped with 3.5 wt % of RD 300 6 ETL Commercial ET/Comparative 350 Compound/Novel compounds doped with 35.0 wt % of Liq 7 EIL Liq 15 8 Cthd Al 1500

[0125] Performance of OLED Device

[0126] 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 Tables 10 to 12. For the blue and red OLED devices, the data of Color coordinates (x,y) were collected at 1000 nits. For the green OLED devices, the data of Color coordinates (x,y) were collected at 3000 nits. For blue OLEDs, the evaluation of lifespan (T85) was defined as a period taken for luminance reduction to 85% of the initial luminance at 2000 nits. The results of blue OLEDs were shown in Table 10.

[0127] For green OLEDs, the evaluation of lifespan (T95) was defined as a period taken for luminance reduction to 95% of the initial luminance at 7000 nits. The results of green OLEDs were shown in Table 11.

[0128] For red OLEDs, the evaluation of lifespan (T90) was defined as a period taken for luminance reduction to 90% of the initial luminance at 6000 nits. The results of red OLEDs were shown in Table 12.

TABLE-US-00011 TABLE 10 materials of ETL, colors, CIE(x), CIE(y), lifespan (T85) of blue OLED devices of Examples 1 to 18 (El to E18) and Comparative Examples 1 to 3 (C1 to C3) Example No. Material of ET CIE(x) CIE(y) T85 (hrs) E1 Compound 1 0.129 0.16 108.70 E2 Compound 2 0.129 0.162 214.11 E3 Compound 3 0.128 0.158 98.04 E4 Compound 4 0.128 0.161 74.63 E5 Compound 5 0.127 0.163 147.06 E6 Compound 6 0.129 0.163 116.28 E7 Compound 7 0.129 0.162 142.86 E8 Compound 8 0.129 0.158 151.52 E9 Compound 9 0.128 0.158 125.00 E10 Compound 10 0.128 0.165 147.06 E11 Compound 11 0.129 0.157 250.00 E12 Compound 12 0.128 0.163 238.10 E13 Compound 13 0.133 0.156 157.46 E14 Compound 14 0.133 0.154 173.98 E15 Compound 15 0.131 0.157 155.32 E16 Compound 16 0.13 0.155 189.84 E17 Compound 17 0.13 0.169 209.84 E18 Compound 18 0.129 0.163 211.25 C1 BCP 0.129 0.154 18.90 C2 TPBi 0.129 0.154 25.60 C3 Comparative 0.129 0.158 65.79 Compound 1

[0129] As shown in Table 10, the lifespans of blue OLEDs of E1 to E18 are all longer than those of C1 to C3, especially for C3. It demonstrated that adopting the novel compounds of the present invention as the electron transport material can effectively prolong the lifespan of the blue OLED.

TABLE-US-00012 TABLE 11 materials of ETL, colors, CIE(x), CIE(y), lifespan (T95) of green OLED devices of Examples 19 to 27 (E19 to E27) and Comparative Examples 4 to 7 (C4 to C7) Example No. Material of ET CIE(x) CIE(y) T95 (hrs) E19 Compound 1 0.312 0.64 157.23 E20 Compound 2 0.313 0.64 131.58 E21 Compound 5 0.314 0.639 161.29 E22 Compound 7 0.311 0.641 135.14 E23 Compound 8 0.31 0.641 138.50 E24 Compound 9 0.317 0.638 185.19 E25 Compound 10 0.31 0.64 151.52 E26 Compound 11 0.312 0.639 185.19 E27 Compound 12 0.311 0.641 156.25 C4 BCP 0.308 0.643 29.00 C5 TPBi 0.31 0.641 38.00 C6 Comparative 0.313 0.64 119.90 Compound 1 C7 Comparative 0.309 0.641 107.30 Compound 2

[0130] As shown in Table 11, the lifespans of green OLEDs of E19 to E27 are all longer than those of C4 to C7, especially for C6 and C7. It demonstrated that adopting the novel compounds of the present invention as the electron transport material also can effectively prolong the lifespan of the green OLED.

TABLE-US-00013 TABLE 12 materials of ETL, colors, CIE(x), CIE(y), lifespan (T90) of red OLED devices of Examples 28 to 34 (E28 to E34) and Comparative Examples 8 to 11 (C8 to C11) Example No. Material of ET CIE(x) CIE(y) T90 (hrs) E28 Compound 2 0.66 0.338 228.21 E29 Compound 3 0.658 0.339 140.43 E30 Compound 5 0.66 0.338 234.43 E31 Compound 7 0.659 0.339 212.36 E32 Compound 9 0.66 0.338 248.69 E33 Compound 11 0.658 0.34 260.97 E34 Compound 12 0.658 0.339 260.97 C8 BCP 659 0.339 35.9 C9 TPBi 0.658 0.338 47.8 C10 Comparative 0.661 0.338 108.39 Compound 1 C11 Comparative 0.66 0.337 156.99 Compound 2

[0131] As shown in Table 12, the lifespans of red OLEDs of E28 to E34 are all longer than those of C8 to C11, especially for C10 and C11. It demonstrated that adopting the novel compounds of the present invention as the electron transport material also can effectively prolong the lifespan of the red OLED, like the blue and green OLEDs.

[0132] Based on the results shown in Tables 10 to 12, the novel compounds of the present invention can be act as the suitable electron transport material and has the effect of prolonging the lifespan of the red, green, and blue OLEDs.

[0133] 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.