COMPOUND, ORGANIC ELECTROLUMINESCENCE MATERIAL, ORGANIC ELECTROLUMINESCENCE ELEMENT AND ELECTRONIC DEVICE

Abstract

The present invention provides a compound, an organic electroluminescence material, an organic electroluminescence element and an electronic device. When the compound is used as the material of the organic functional layers, it makes the element have a lower driving voltage, a higher current efficiency and a longer service life.

Claims

1. A compound, characterized in that the compound has a structure represented by Formula (1): ##STR00153## wherein, R is selected from hydrogen, deuterium, halogen, a cyano group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group; R.sup.1 is -L.sup.1Ar.sup.1; R.sup.2 is -L.sup.2Ar.sup.2; R.sup.3 is -L.sup.3Ar.sup.3; R.sup.4 is -L.sup.4Ar.sup.4; L.sup.1 to L.sup.4 are each independently selected from a bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; and Ar.sup.1 to Ar.sup.4 are each independently selected from hydrogen, deuterium, halogen, a cyano group, a substituted or unsubstituted C6-C60 arylamino group, a substituted or unsubstituted C3-C60 heteroarylamino group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group.

2. The compound as claimed in claim 1, characterized in that Ar.sup.1 to Ar.sup.4 are each independently selected from hydrogen, deuterium, halogen, and a group selected from a phenyl group, a naphthyl group, a biphenylyl group, a phenanthryl group, a fluoranthenyl group, a benzophenanthryl group, a terphenylyl group, a triphenylenylene group, a dimethylfluorenyl group, a diphenylfluorenyl group, a spiro-bifluorenyl group, a benzodimethylfluorenyl group, a benzodiphenylfluorenyl group, a benzo-spiro-bifluorenyl group, a dibenzofuryl group, a benzonaphthofuryl group and a benzonaphthothiophenyl group, and a dibenzothiophenyl group, each of which is substituted or unsubstituted.

3. The compound as claimed in claim 1, characterized in that at least one of Ar.sup.1 to Ar.sup.4 is selected from a group represented by Formula a: ##STR00154## X.sup.1 is selected from N and CR.sup.X1; X.sup.2 is selected from N and CR.sup.X2; X.sup.3 is selected from N and CR.sup.X3; X.sup.4 is selected from N and CR.sup.X4; X.sup.5 is selected from N and CR.sup.X5; R.sup.X1 to R.sup.X5 are each independently selected from hydrogen, deuterium, halogen, a cyano group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group; R.sup.X1 to R.sup.X5 are present individually without forming a ring, or any adjacent two of R.sup.X1 to R.sup.X5 joined to form a ring A, and the ring A is a substituted or unsubstituted C6-C30 aromatic ring, or a substituted or unsubstituted C3-C30 heteroaromatic ring.

4. The compound as claimed in claim 3, characterized in that the ring A is a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a benzothiophene ring, a benzofuran ring, or an indene ring; R.sup.X1 to R.sup.X5 are each independently selected from hydrogen, deuterium, halogen, and a group selected from a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a phenanthryl group, an anthryl group, a phenylnaphthyl group, a naphthylphenyl group, a pyridyl group, a bipyridyl group, a dibenzofuryl group, a dibenzothiophenyl group, a carbazolyl group, a carbazolylphenyl group, a phenylcarbazolyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a spiro-bifluorenyl group, a dibenzofurylphenyl group, a dibenzothiophenylphenyl group, a dimethylfluorenylphenyl group, a benzocarbazolyl group, a benzonaphthofuryl group and a benzonaphthothiophenyl group, each of which is substituted or unsubstituted; and in X.sup.1 to X.sup.5, X.sup.1 is N; X.sup.2 is N; X.sup.3 is CR.sup.X3; X.sup.4 is CR.sup.X4; and X.sup.5 is CR.sup.X5; or X.sup.1 is N; X.sup.3 is N; X.sup.2 is CR.sup.X2; X.sup.4 is CR.sup.X4; and X.sup.5 is CR.sup.X5; or X.sup.1 is N; X.sup.2 is N; X.sup.3 is N; X.sup.4 is CR.sup.X4; and X.sup.5 is CR.sup.X5.

5. The compound as claimed in claim 1, characterized in that at least one of Ar.sup.1 to Ar.sup.4 is selected from a group represented by Formula b: ##STR00155## Ar.sup.5 to Ar.sup.6 are each independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted and unsubstituted C3-C30 heteroaryl group.

6. The compound as claimed in claim 5, characterized in that Ar.sup.5 to Ar.sup.6 are each independently selected from a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a phenanthryl group, an anthryl group, a triphenylenylene group, a phenylnaphthyl group, a naphthylphenyl group, a pyridyl group, a bipyridyl group, a dibenzofuryl group, a dibenzothiophenyl group, a benzonaphthofuryl group, a benzonaphthothiophenyl group, a dinaphthofuryl group, a dinaphthothiophenyl group, a dibenzofurylphenyl group, a dibenzothiophenylphenyl group, a dimethylfluorenyl group, a benzodimethylfluorenyl group, a diphenylfluorenyl group, a spiro-bifluorenyl group, and a dimethylfluorenylphenyl group.

7. The compound as claimed in claim 1, characterized in that at least one of Ar.sup.1 to Ar.sup.4 is selected from a group represented by Formula c: ##STR00156## R.sup.T1 to R.sup.T8 are each independently selected from hydrogen, deuterium, halogen, a cyano group, a substituted or unsubstituted C1-C30 alkyl group, a C1-C30 alkyl group in which one or more methylene groups are independently substituted by —O— and/or —S— in a manner that O atom and/or S atom are not adjacent to each other, a substituted or unsubstituted C7-C30 arylalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C4-C30 heteroarylalkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 heterocycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, and a substituted or unsubstituted C6-C30 aryloxy group; R.sup.T1 to R.sup.T8 are present individually without forming a ring, or any adjacent two of R.sup.T1 to R.sup.T8 joined to form a ring B, and the ring B is a substituted or unsubstituted C6-C30 aromatic ring, or a substituted or unsubstituted C6-C30 heteroaromatic ring.

8. The compound as claimed in claim 7, characterized in that the Formula c is selected from any of the c-1, c-2, c-3, c-4, c-5 and c-6: ##STR00157## R.sup.T1 to R.sup.T8 are each independently selected from hydrogen, deuterium, and a group selected from a methyl group, an ethyl group, a tert-butyl group, an adamantyl group, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a phenanthryl group, an anthryl group, a triphenylenylene group, a phenylnaphthyl group, a naphthylphenyl group, a pyridyl group, a bipyridyl group, a dibenzofuryl group, a dibenzothiophenyl group, a benzonaphthofuryl group, a benzonaphthothiophenyl group, a dinaphthofuryl group, a dinaphthothiophenyl group, a dibenzofurylphenyl group, a dibenzothiophenylphenyl group, a dimethylfluorenyl group, a benzodimethylfluorenyl group, a diphenylfluorenyl group, a spiro-bifluorenyl group and a dimethylfluorenylphenyl group, each of which is substituted or unsubstituted.

9. The compound as claimed in claim 1, characterized in that L.sup.1 to L.sup.4 are each independently selected from a bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, and a substituted or unsubstituted naphthylene group.

10. The compound as claimed in claim 1, characterized in that the compound is a compound M having electron transport properties or a compound N having hole transport properties; the compound M is any one of compounds M1 to M206: ##STR00158## ##STR00159## ##STR00160## ##STR00161## ##STR00162## ##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171## ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184## ##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190## ##STR00191## ##STR00192## ##STR00193## ##STR00194## ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## ##STR00201## ##STR00202## ##STR00203## ##STR00204## ##STR00205## ##STR00206## ##STR00207## ##STR00208## ##STR00209## ##STR00210## ##STR00211## ##STR00212## ##STR00213## ##STR00214## ##STR00215## ##STR00216## ##STR00217## ##STR00218## ##STR00219## ##STR00220## ##STR00221## ##STR00222## ##STR00223## ##STR00224## ##STR00225## ##STR00226## and the compound N is an one of compounds N1 to N115: ##STR00227## ##STR00228## ##STR00229## ##STR00230## ##STR00231## ##STR00232## ##STR00233## ##STR00234## ##STR00235## ##STR00236## ##STR00237## ##STR00238## ##STR00239## ##STR00240## ##STR00241## ##STR00242## ##STR00243## ##STR00244## ##STR00245## ##STR00246## ##STR00247## ##STR00248## wherein D represents deuterium.

11. An organic electroluminescence material, characterized in that the organic electroluminescence material comprises the compound as claimed in claim 1.

12. The organic electroluminescence material as claimed in claim 11, characterized in that the organic electroluminescence material comprises at least one of compounds M1 to M206 and at least one of compounds N1 to N115.

13. An organic electroluminescence element, characterized in that the organic electroluminescence element comprises a first electrode, a second electrode and an organic layer disposed between the first electrode and the second electrode; and the organic layer is made of a material comprising the compound as claimed in claim 1.

14. An electronic device, characterized in that the electronic device comprises the organic electroluminescence element as claimed in claim 13.

Description

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0094] Specific embodiments are further illustrated by the following examples to demonstrate the technical approaches of the present invention. Those skilled in the art should understand that the illustrative examples are helpful to understand the present invention; however, they should not be construed as being limiting to the scope of the present invention.

Preparation Examples of Compound of the Present Invention

[0095] ##STR00107## ##STR00108##

[0096] Synthesis of M6-B: In a three-necked bottle of 25 milliliters (mL), M6-A (10 millimoles (mmol)), nitrobenzene (10 mmol), potassium hydroxide (22 mmol), copper(I) thiocyanate (1 mmol) and anhydrous tetrahydrofuran (10 mL) were added, nitrogen gas was purged for three times, and heated to 90° C. under nitrogen gas protection to react for 48 hours (h). After the reaction ended, the reaction mixture was quenched by water, the reaction system was extracted by ethyl acetate, and the organic solvent was removed by rotary evaporation to give a crude product. The crude product was purified by column chromatography (ethyl acetate:n-hexane=1:50 (volume ratio)), to obtain M6-B (1.34 g, 49% yield).

[0097] Synthesis of M6-B′: In a three-necked bottle of 50 mL, 2-bromo-4-chlorobenzaldehyde (10 mmol), bis(pinacolato)diboron (12 mmol), potassium acetate (100 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.2 mmol) and 1,4-dioxane (25 mL) were added, nitrogen gas was purged, and heated to 100° C. under nitrogen gas protection for reaction. After the reaction ended, the reaction mixture was quenched by water, extracted by methylene dichloride to give a crude product. The crude product was purified by column chromatography (methylene dichloride:n-hexane=1:50 (volume ratio)), to obtain M6-B′ (1.7 g, 64% yield).

[0098] Synthesis of M6-C: In a three-necked bottle of 50 mL, M6-B (10 mmol), M6-B′ (10 mmol), sodium bicarbonate (20 mmol), tetrakis(triphenylphosphine)palladium (0.2 mmol), tetrahydrofuran (20 mL) and water (10 mL) were added, nitrogen gas was purged, and heated to 60° C. under nitrogen gas protection to react overnight. After the reaction ended, the reaction mixture was quenched by water, extracted by methylene dichloride, and the organic solvent was removed by rotary evaporation to give a crude product. The crude product was purified by column chromatography (ethyl acetate:n-hexane=1:50 (volume ratio)), to obtain M6-C (3.06 g, 92% yield).

[0099] Synthesis of M6-D: In a three-necked bottle of 50 mL, M6-C (10 mmol), (methoxymethyl)triphenylphosphonium chloride (20 mmol), tetrahydrofuran (10 mL) were added, and the temperature was reduced to 0° C. Potassium tert-butoxide (2 mmol) was resolved in 5 mL tetrahydrofuran. The three-necked bottle was purged with nitrogen gas. Under nitrogen gas protection, the potassium tert-butoxide solution was added dropwise at 0° C. to obtain a mixture. After the addition, the mixture was stirred to react for half an hour. After the reaction ended, the reaction mixture was quenched by water, extracted by methylene dichloride, and the organic solvent was removed by rotary evaporation to give a crude product. The crude product was purified by column chromatography (ethyl acetate:n-hexane=1:50 (volume ratio)), to obtain M6-D (1.8 g, 50% yield).

[0100] Synthesis of M6-E: In a three-necked bottle of 25 mL, M6-D (1 mmol) and hexafluoroisopropanol (5 mL) were added, the temperature was reduced to 0° C., and nitrogen gas was purged. Under nitrogen gas protection, trifluoromethanesulfonic acid (1 mL) was added dropwise to obtain a mixture, and the mixture was stirred to react for half an hour to give a crude product. The crude product was purified by column chromatography (ethyl acetate:n-hexane=1:50 (volume ratio)), to obtain M6-E (0.24 g, 73% yield).

[0101] Synthesis of M6-F: In a three-necked bottle of 50 mL, M6-E (10 mmol), bis(pinacolato)diboron (12 mmol), sodium acetate (20 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.5 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.5 mmol) were added, then 1,4-dioxane (20 mL) was added, nitrogen gas was purged for three times, and heated to 100° C. under nitrogen gas protection for reaction. After the reaction ended, the reaction mixture was quenched by water, extracted by methylene dichloride, and the organic solvent was removed by rotary evaporation to give a crude product. The crude product was purified by column chromatography (ethyl acetate:n-hexane=1:50 (volume ratio)), to obtain M6-F (3.24 g, 77% yield).

[0102] Synthesis of M6: In a three-necked bottle of 100 mL, a stir bar was put at the bottom and a refluxing tube was connected on the top. The bottle was dried and purged with nitrogen gas, and M6-F (10 mmol), M6-G (10 mmol CAS1689576-03-1), sodium bicarbonate (23 mmol), tetrakis(triphenylphosphine)palladium (0.5 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine) dichloropalladium(II) (0.5 mmol), toluene (25 mL), ethanol (7 mL) and water (7 mL) were separately added, nitrogen gas was purged for three times, and heated to 80° C. to react for 8 h. After the reaction ended, the reaction mixture was extracted by ethyl acetate, and the resulting extract was dried by magnesium sulfate, filtered, and dried by rotary evaporation to give a crude product. The crude product was purified by column chromatography (ethyl acetate:n-hexane=1:10 (volume ratio)), to obtain compound M6 (4.13 g, 69% yield).

[0103] Anal. Calcd. C.sub.41H.sub.26N.sub.6: C, 81.71; H, 4.35; N, 13.94. Found: C, 81.78; H, 4.33; N, 13.89. HRMS (ESI) m/z [M+H].sup.+: Calcd.: 602.22. Found: 603.40.

##STR00109## ##STR00110##

[0104] Synthesis of M160-B″: Similar to the synthesis of M6-B′, with the difference that 2-bromo-5-chlorobenzaldehyde is used to replace 2-bromo-4-chlorobenzaldehyde, to obtain M160-B″ (1.60 g, 60% yield).

[0105] Synthesis of M160-C: Similar to the synthesis of M6-C, with the difference that 4-fluoro-2-formylbenzeneboronic acid pinacol ester is used to replace 5-fluoro-2-formylbenzeneboronic acid pinacol ester, to obtain M160-C (2.13 g, 64% yield).

[0106] Synthesis of M160-D: Similar to the synthesis of M6-D, with the difference that M160-C is used to replace M6-C, to obtain M160-D (3.21 g, 89% yield).

[0107] Synthesis of M160-E: Similar to the synthesis of M6-E, with the difference that M160-D is used to replace M6-D, to obtain M160-E (0.16 g, 48% yield).

[0108] Synthesis of M160-F: Similar to the synthesis of M6-F, with the difference that M160-E is used to replace M6-E, to obtain M160-F (4.00 g, 95% yield).

[0109] Synthesis of M160: Similar to the synthesis of M6, with the difference that M160-F is used to replace M6-F, and M160-G is used to replace M6-G, to obtain M160 (4.70 g, 78% yield).

[0110] Anal. Calcd. C.sub.41H.sub.26N.sub.6: C, 81.71; H, 4.35; N, 13.94. Found: C, 81.73; H, 4.37; N, 13.90. HRMS (ESI) m/z (M.sup.+): Calcd.: 602.22. Found: 603.29.

[0111] The corresponding products shown in Table 1 were prepared by the above-mentioned preparation method using the Material 1 and Material 2 as raw materials. The structure and characteristic data of the products are shown in Table 2.

TABLE-US-00001 TABLE 1 Material 1 Material 2 Product Yield (%) [00111] [00112]   CAS2142681-84-1 [00113] 65 M46 [00114] [00115]   CAS2391956-00-4 [00116] 67 M41 [00117] [00118]   CAS1618106-98-1 [00119] 74 M23 [00120] [00121]   CAS2102445-28-1 [00122] 65 M97 [00123] [00124]   CAS1413365-66-8 [00125] 68 M117 [00126] [00127]   CAS2286234-09-9 [00128]   M93 68 [00129] [00130] [00131]   N2 63 CAS 1313514-53-2 [00132] [00133]   CAS 1556069-52-3 [00134] 63 N76 [00135] [00136]   CAS 1268244-56-9 [00137] 61 M31

TABLE-US-00002 TABLE 2 HRMS (ESI) Com- Elemental analysis m/z [M + H].sup.+ pound Calcd. Found Calcd. Found M46 C, 79.85; H, 3.92; N, C, 79.92; H, 3.91; N, 616.20 617.26 13.63; 13.59; M41 C, 79.21; H, 4.70; N, C, 79.24; H, 4.71; N, 621.23 622.26 13.52; 13.48; M23 C, 82.22; H, 4.70; N, C, 82.16; H, 4.72; N, 642.25 643.25 13.08; 13.12; M97 C, 81.49; H, 4.07; N, C, 81.53; H, 4.08; N, 692.23 693.20 12.13; 12.08; M117 C, 83.46; H, 4.38; N, C, 83.39; H, 4.40; N, 575.21 576.24 12.17; 12.21; M93 C, 81.93; H, 4.09; N, C, 81.89; H, 4.11; N, 615.21 616.17 11.37; 11.40; N2 C, 88.42; H, 4.55; N, C, 88.47; H, 4.53; N, 597.22 598.20 7.03; 7.00; N76 C, 89.32; H, 4.56; N, C, 89.28; H, 4.57; N, 685.25 686.28 6.13; 6.15; M31 C, 79.98; H, 4.09; N, C, 80.04; H, 4.08; N, 615.22 616.16 15.92; 15.88;

##STR00138##

[0112] Synthesis of compound N51: In a three-necked bottle of 25 mL, nitrogen gas was purged, and then M6-E (1 mmol), compound N51-G (1 mmol), sodium tert-butoxide (2 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.02 mmol), 50% tri-tert-butylphosphine solution (0.1 mmol) and toluene 8 mL was added, and stirred under reflux for reaction. After the reaction ended, the reaction mixture was cooled to room temperature, and the organic layer was extracted by ethyl acetate and H.sub.2O, and the extracted organic layer was dried by magnesium sulfate, filtered, and the filtrate was concentrated under vacuum to give a crude product. The crude product was purified by column chromatography (ethyl acetate:n-hexane=1:50 (volume ratio)), to obtain compound N51 (0.50 g, 71% yield).

[0113] Anal. Calcd. C.sub.50H.sub.32N.sub.4O: C, 85.20; H, 4.58; N, 7.95. Found: C, 85.21; H, 4.60; N, 7.92. HRMS (ESI) m/z [M+H].sup.+: Calcd.: 704.26. Found: 705.31.

##STR00139##

[0114] Synthesis of compound N44: In a two-necked bottle of 25 mL, a stir bar was put at the bottom and a refluxing tube was connected on the top. The bottle was dried and purged with nitrogen gas, and M6-F (0.01 mol), N44-G (0.01 mol), potassium carbonate (0.013 mol), tetrakis(triphenylphosphine)palladium (0.5 mmol), toluene (10 mL) and water (4 mL) was separately added, nitrogen gas was purged for three times, and heated to 85° C. under nitrogen gas protection to react for 10 h. After the reaction ended, the reaction mixture was extracted by ethyl acetate, and the extracted solution was dried by magnesium sulfate, filtered, and dried by rotary evaporation to give a crude product. The crude product was purified by column chromatography (ethyl acetate:n-hexane=1:10 (volume ratio)), to obtain compound N44 (4.44 g, 63% yield).

[0115] Anal. Calcd. C.sub.50H.sub.32N.sub.4O: C, 85.20; H, 4.58; N, 7.95. Found: C, 85.16; H, 4.60; N, 7.98. HRMS (ESI) m/z (M.sup.+): Calcd.: 704.26. Found: 705.28.

[0116] The corresponding products shown in Table 3 were prepared by the above-mentioned preparation method using the Material 1 and Material 2 as raw materials. The structure and characteristic data of the products are shown in Table 4.

TABLE-US-00003 TABLE 3 Material 1 Material 2 Product Yield % [00140] [00141]   CAS 194-59-2 [00142] 62 N12 [00143] [00144]   CAS 1429933-62-9 [00145] 60 N60 [00146] [00147]   CAS32228-99-2 [00148] 61 N83 [00149] [00150] [00151] 64 CAS 1263001-82-6 N40

TABLE-US-00004 TABLE 4 HRMS (ESI) Com- Elemental analysis m/z [M + H].sup.+ pound Calcd. Found Calcd. Found N12 C, 85.69; H, 4.31; N, C, 85.75; H, 4.29; 560.20 561.11 9.99 N, 9.96 N60 C, 81.96; H, 4.38; N, C, 81.91; H, 4.40; 644.20 645.30 8.69; S, 4.97 N, 8.71; S, 4.98 N83 C, 84.73; H, 4.87; N, C, 84.70; H, 4.85; 538.22 539.31 10.40 N, 10.45 N40 C, 85.96; H, 5.13; N, C, 86.01; H, 5.10; 628.26 629.33 8.91 N, 8.89

Element Examples 1 to 16 and Comparative Element Examples 1 to 2

[0117] An organic electroluminescence element having the following layer structure was provided: base (indium tin oxide (ITO) coated glass substrate, as an anode)/hole injection layer (HIL)/hole transport layer (HTL)/emitting layer (EML)/electron transport layer (ETL)/electron injection layer (EIL), and the cathode at last.

[0118] The materials needed to prepare OLEDs are listed below, wherein the REF-1 is comparative compound 1:

##STR00152##

[0119] The above-mentioned organic electroluminescence element was prepared by the following steps:

[0120] (1) Cleaning the substrate: a glass substrate coated with transparent ITO (the anode layer) was ultrasonicated in an aqueous detergent (the content and concentration of the aqueous detergent: an ethylene glycol solvent of ≤10 percent by weight (wt %), triethanolamine of ≤1 wt %), washed in deionized water, degreased in an acetone/ethanol mixed solvent (volume ratio=1:1) by ultrasonication, baked in a clear environment until water was completely removed, and washed by ozone under ultraviolet light;

[0121] (2) Depositing emitting functional layers:

[0122] The glass substrate with the anode layer was placed in a chamber, and the chamber was vacuumized until 1×10.sup.−6 Pascal (Pa) to 2×10.sup.−4 Pa, and a mixture of NDP-9 and HT (mass ratio of NDP-9 and HT is 3:97) was deposited on the anode layer in vacuum to form a hole injection layer, in which the deposited thickness was 10 nanometers (nm).

[0123] A hole transport layer (material: HT) was deposited on the hole injection layer, in which the deposited thickness was 80 nm.

[0124] An emitting layer was deposited on the hole transport layer. Specifically, the preparation method was: the light-emitting host material (materials shown in Table 5) and a guest material (piq).sub.2Ir(acac) were co-deposited in vacuum, in which the total deposited thickness was 30 nm.

[0125] An electron transport layer was deposited on the emitting layer. Specifically, the preparation method was: the electron transport layer materials (shown in Table 5) were co-deposited in vacuum, in which the total deposited thickness was 30 nm.

[0126] An electron injection layer (material: LiQ) was deposited on the electron transport layer, in which the total deposited thickness was 1 nm.

[0127] Al (cathode) was deposited on the electron injection layer, in which the deposited thickness was 80 nm.

[0128] The materials (mat.) of each layer in the element and parameters such as thickness (thk.) of Element Examples 1 to 16 (E1 to E16) and Comparative Element Examples 1 to 2 (CE1 to CE2) are shown in Table 5.

TABLE-US-00005 TABLE 5 HIL mat./ HTL mat./ EML mat./ ETL mat./ EIL mat./ Cathode mat./ No. thk. thk. thk. thk. thk. thk. E1 NDP-9:HT HT/ CBP:(piq).sub.2Ir(acac) compoundM6:LiQ/ LiQ/ Al/ (mass ratio 80 nm (mass ratio (mass ratio 1 nm 80 nm 3:97)/10 nm 95:5)/30 nm 1:1)/30 nm E2 NDP-9:HT HT/ compound M6:compound ET-1:LiQ LiQ/ Al/ (mass ratio 80 nm N12:(piq).sub.2Ir(acac) (mass ratio 1 nm 80 nm 3:97)/10 nm (mass ratio 1:1)/30 nm 47.5:47.5:5)/30 nm E3 NDP-9:HT HT/ compound M46:compound ET-1:LiQ LiQ/ Al/ (masratio 80 nm N40:(piq).sub.2Ir(acac) (mass ratio 1 nm 80 nm 3:97)/10 nm (mass ratio 1:1)/30 nm 47.5:47.5:5)/30 nm E4 NDP-9:HT HT/ compound M41:compound ET-1:LiQ LiQ/ Al/ (mass ratio 80 nm N40:(piq).sub.2Ir(acac) (mass ratio 1 nm 80 nm 3:97)/10 nm (mass ratio 1:1)/30 nm 47.5:47.5:5)/30 nm E5 NDP-9:HT HT/ compound M23:compound ET-1:LiQ LiQ/ Al/ (mass ratio 80 nm N60:(piq).sub.2Ir(acac) (mass ratio 1 nm 80 nm 3:97)/10 nm (mass ratio 1:1)/30 nm 47.5:47.5:5)/30 nm E6 NDP-9:HT HT/ compound M97:compound ET-1:LiQ LiQ/ Al/ (mass ratio 80 nm N51:(piq).sub.2Ir(acac) (mass ratio 1 nm 80 nm 3:97)/10 nm (mass ratio 1:1)/30 nm 47.5:47.5:5)/30 nm E7 NDP-9:HT HT/ compound M97:compound ET-1:LiQ LiQ/ Al/ (mass ratio 80 nm N76:(piq).sub.2Ir(acac) (mass ratio 1 nm 80 nm 3:97)/10 nm (mass ratio 1:1)/30 nm 47.5:47.5:5)/30 nm E8 NDP-9:HT HT/ compound M117:compound ET-1:LiQ LiQ/ Al/ (mass ratio 80 nm N2:(piq).sub.2Ir(acac) (mass ratio 1 nm 80 nm 3:97)/10 nm (mass ratio 1:1)/30 nm 47.5:47.5:5)/30 nm E9 NDP-9:HT HT/ compound M93:compound ET-1:LiQ LiQ/ Al/ (mass ratio 80 nm N60:(piq).sub.2Ir(acac) (mass ratio 1 nm 80 nm 3:97)/10 nm (mass ratio 1:1)/30 nm 47.5:47.5:5)/30 nm E10 NDP-9:HT HT/ compound M160:compound ET-1:LiQ LiQ/ Al/ (mass ratio 80 nm N40:(piq).sub.2Ir(acac) (mass ratio 1 nm 80 nm 3:97)/10 nm (mass ratio 1:1)/30 nm 47.5:47.5:5)/30 nm E11 NDP-9:HT HT/ compound M31:compound ET-1:LiQ LiQ/ Al/ (mass ratio 80 nm N60:(piq).sub.2Ir(acac) (mass ratio 1 nm 80 nm 3:97)/10 nm (mass ratio 1:1)/30 nm 47.5:47.5:5)/30 nm E12 NDP-9:HT HT/ compound M97:compound ET-1:LiQ LiQ/ Al/ (mass ratio 80 nm N44:(piq).sub.2Ir(acac) (mass ratio 1 nm 80 nm 3:97)/10 nm (mass ratio 1:1)/30 nm 47.5:47.5:5)/30 nm E13 NDP-9:HT HT/ compound M117:compound ET-1:LiQ LiQ/ Al/ (mass ratio 80 nm N83:(piq).sub.2Ir(acac) (mass ratio 1 nm 80 nm 3:97)/10 nm (mass ratio 1:1)/30 nm 47.5:47.5:5)/30 nm E14 NDP-9:HT HT/ M117:(piq).sub.2Ir(acac) ET-1:LiQ LiQ/ Al/ (mass ratio 80 nm (mass ratio (mass ratio 1 nm 80 nm 3:97)/10 nm 95:5)/30 nm 1:1)/30 nm E15 NDP-9:HT HT/ compound ET-1:LiQ LiQ/ Al/ (mass ratio 80 nm M6:CBP:(piq).sub.2Ir(acac) (mass ratio 1 nm 80 nm 3:97)/10 nm (mass ratio 1:1)/30 nm 47.5:47.5:5)/30 nm E16 NDP-9:HT HT/ compound ET-1:LiQ LiQ/ Al/ (mass ratio 80 nm N51:CBP:(piq).sub.2Ir(acac) (mass ratio 1 nm 80 nm 3:97)/10 nm (mass ratio 1:1)/30 nm 47.5:47.5:5)/30 nm CE1 NDP-9:HT HT/ CBP:(piq).sub.2Ir(acac) ET-1:LiQ LiQ/ Al/ (mass ratio 80 nm (mass ratio (mass ratio 1 nm 80 nm 3:97)/10 nm 95:5)/30 nm 1:1)/30 nm CE2 NDP-9:HT HT/ REF-1:CBP:(piq).sub.2Ir(acac) ET-1:LiQ LiQ/ Al/ (mass ratio 80 nm (mass ratio (mass ratio 1 nm 80 nm 3:97)/10 nm 47.5:47.5:5)/30 nm 1:1)/30 nm

[0129] Characteristic Tests:

[0130] Instruments: the characteristics such as current, voltage, luminance and the like of the elements of the above Element Examples 1 to 16 and Comparative Element Examples 1 to 2 were synchronously tested by PR 650 SpectraScan Colorimeter and Keithley K 2400 SourceMeter;

[0131] Testing conditions of Element Examples 1 to 16 and Comparative Element Examples 1 to 2:

[0132] Conditions for testing electrooptical characteristics: a current density of 10 milliamperes/square centimeter (mA/cm.sup.2) under room temperature;

[0133] Service life test: tested with a current density of 50 mA/cm.sup.2 under room temperature, and the time period recorded when the luminance of the tested element was reduced to 98% of the original luminance (in hour).

[0134] The test results of the elements are shown in Table 6.

TABLE-US-00006 TABLE 6 Driving Current efficiency Service No. voltage (V) (Cd/A) life (h) E1 4.4 12 21 E2 3.8 21 66 E3 3.8 20 75 E4 3.8 22 70 E5 3.9 21 65 E6 3.9 20 69 E7 3.9 21 67 E8 3.8 21 62 E9 3.9 20 64 E10 4.0 18 50 E11 3.9 20 60 E12 3.9 19 54 E13 4.0 18 56 E14 4.1 17 30 E15 4.1 16 35 E16 4.2 16 33 CE1 4.8 5 5 CE2 4.6 8 12

[0135] From Table 6, it is clear that the compounds developed by the present invention obviously increase the charge carrier injection efficiency, reduce the energy level difference between layers, balance the electron- and hole-transport efficiency, thereby effectively increase the efficiency of the organic electroluminescence device, and prolong the service life of the organic electroluminescence device. When the organic electroluminescence material is used as the material of the organic functional layer, it makes the element have a lower driving voltage (4.4 voltages (V) or lower, especially to 4.0 V or lower), a higher current efficiency (12 Candelas/Ampere (Cd/A) or more, especially to 18 Cd/A or more) and a longer service life (15 h or more, especially to 50 h or more).

[0136] The applicant claims herein that even though the organic electroluminescence material of the present invention and the organic electroluminescence device and electronic products comprising organic electroluminescence material are demonstrated by the above examples, the scope of the present invention is not limited by these examples. That is to say, it does not mean that the present invention has to be carried out based on the above examples. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of materials, addition of auxiliary components, selection of specific means and the like are all within the scope of protection and disclosure of the present invention.