ORGANIC MATERIAL COMPOSITION AND APPLICATIONS THEREOF

Abstract

The present invention provides an organic material composition and applications thereof. By the combination of the compounds comprised in the organic material composition, the organic material composition makes the element have a lower driving voltage, a higher current efficiency and a longer service life.

Claims

1. An organic material composition, wherein the organic material composition comprises at least one compound having a structure represented by Formula 1 and at least one compound having a structure represented by Formula 2: ##STR00156## 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; ##STR00157## Z.sup.1 is selected from N and CL.sup.Y1Ar.sup.Y1; Z.sup.2 is selected from N and CL.sup.Y2Ar.sup.Y2; Z.sup.3 is selected from N and CL.sup.Y3Ar.sup.Y3; Z.sup.4 is selected from N and CL.sup.Y4Ar.sup.Y4; Z.sup.5 is selected from N and CL.sup.Y5Ar.sup.Y5; Z.sup.6 is selected from N and CL.sup.Y6Ar.sup.Y6; L.sup.Y1, L.sup.Y2, L.sup.Y3, L.sup.Y4, L.sup.Y5 and L.sup.Y6 are each independently selected from a bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; Ar.sup.Y1, Ar.sup.Y2, Ar.sup.Y3, Ar.sup.Y4, Ar.sup.Y5 and Ar.sup.Y6 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-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group; and L.sup.Y1Ar.sup.Y1, L.sup.Y2Ar.sup.Y2, L.sup.Y3Ar.sup.Y3, L.sup.Y4Ar.sup.Y4, L.sup.Y5Ar.sup.Y5 and L.sup.Y6Ar.sup.Y6 are present individually without forming a ring, or any adjacent two of L.sup.Y1Ar.sup.Y1, L.sup.Y2Ar.sup.Y2, L.sup.Y3Ar.sup.Y3, L.sup.Y4Ar.sup.Y4, L.sup.Y5Ar.sup.Y5 and L.sup.Y6Ar.sup.Y6 joined to form a substituted or unsubstituted C6-C30 aromatic ring, or a substituted or unsubstituted C3-C30 heteroaromatic ring.

2. The organic material composition according to claim 1, wherein in Formula 1, at least one of Ar.sup.1 to Ar.sup.4 is a group represented by Formula b: ##STR00158## Ar.sup.5 and Ar.sup.6 are each independently selected from a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group.

3. The organic material composition according to claim 2, wherein in Formula 1, at least one of Ar.sup.1 to Ar.sup.4 is ##STR00159## Ar.sup.1 to Ar.sup.4 are each independently selected from hydrogen, deuterium, and a group selected from a phenyl group, a naphthyl group, a biphenylyl group, a terphenylyl group, a phenanthryl group, a fluoranthenyl 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 dibenzothiophenyl group, a carbazolyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, each of which is substituted or unsubstituted; 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.

4. The organic material composition according to claim 2, wherein in Formula 1, R is selected from a phenyl group and a biphenylyl group, each of which is substituted or unsubstituted; at least one of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 is hydrogen; when R.sup.1, R.sup.2, R.sup.3 or R.sup.4 is not hydrogen, L.sup.1 to L.sup.4 are each independently selected from a bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, and a substituted or unsubstituted terphenylene group; and at least one of Ar.sup.1 to Ar.sup.4 is a group represented by Formula b, and Formula b is any one selected from b−1, b−2, b−3, b−4, b−5 and b−6 as below: ##STR00160## 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 adamantly, 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; Ar.sup.1 to Ar.sup.4 are each independently selected from hydrogen, deuterium, and a group selected from a phenyl group, a naphthyl group, a biphenylyl group, a terphenylyl group, a phenanthryl group, a fluoranthenyl 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 dibenzothiophenyl group, a carbazolyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, each of which is substituted or unsubstituted.

5. The organic material composition according to claim 1, wherein the compound having a structure represented by Formula 1 is selected from the following compounds: ##STR00161## ##STR00162## ##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171## ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179##

6. The organic material composition according to claim 1, wherein the compound having a structure represented by Formula 2 is the compound having a structure represented by Formula 2-1, wherein at least two of Z.sup.1, Z.sup.3 and Z.sup.5 are N; ##STR00180## wherein, in Z.sup.1, Z.sup.3 and Z.sup.5, Z.sup.1 and Z.sup.3 are N, and Z.sup.5 is CL.sup.Y5Ar.sup.5, in which L.sup.Y5Ar.sup.Y5 and L.sup.Y6Ar.sup.Y6 are present individually without forming a ring, or joined to form a substituted or unsubstituted benzene ring; or Z.sup.1 and Z.sup.5 are N, and Z.sup.3 is CL.sup.Y3Ar.sup.Y3; or Z.sup.3 and Z.sup.5 are N, and Z.sup.1 is CL.sup.Y1Ar.sup.Y1; or Z.sup.1, Z.sup.3, and Z.sup.5 are N; and wherein, Ar.sup.Y1, Ar.sup.Y2, Ar.sup.Y3, Ar.sup.Y4, Ar.sup.Y5 and Ar.sup.Y6 are each independently selected from hydrogen, deuterium, halogen, a cyano group, and a group selected from a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a phenylnaphthyl group, a naphthylphenyl group, a triphenylenylene group, an anthryl group, a phenanthryl group, a chrysenyl group, each of which is substituted or unsubstituted; and a group represented by Formula 3: ##STR00181## Y is selected from O, S, and CR.sup.W1R.sup.W2; when at least one of Ar.sup.Y1, Ar.sup.Y2, Ar.sup.Y3, Ar.sup.Y4, Ar.sup.Y5 and Ar.sup.Y6 is selected from Formula 3, any one of R.sup.1 to R.sup.Y8, R.sup.W1 and R.sup.W2 in Formula 3 is connected to L.sup.Y2, L.sup.Y4 or L.sup.Y6 in Formula 2-1 by chemical bonding; Ar.sup.Y1, Ar.sup.Y2, Ar.sup.3, Ar.sup.Y4, Ar.sup.Y5 and Ar.sup.Y6 are the same or different; R.sup.Y1 to R.sup.Y8 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.Y1 to R.sup.Y8 are present individually without forming a ring, or any adjacent two of R.sup.Y1 to R.sup.Y8 joined to form a ring A, and the ring A is a substituted or unsubstituted C6-C30 aromatic ring; R.sup.W1 and R.sup.W2 are selected from a substituted or unsubstituted C1-C30 alkyl group, and a substituted or unsubstituted C6-C30 aryl group.

7. The organic material composition according to claim 6, wherein the group represented by Formula 3 is any one selected from the following groups: ##STR00182## R.sup.W1 and R.sup.W2 are each independently selected from a methyl group and a phenyl group; or R.sup.W1 and R.sup.W2 joined to form a spiro ring; R.sup.Y1—R.sup.Y8 are each independently selected from hydrogen, deuterium, and a group selected from a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a phenylnaphthyl group, a naphthylphenyl group, an anthryl group, a phenanthryl group, a benzophenanthryl group, a pyridyl group, a dibenzofuryl group, a dibenzothiophenyl group, a dibenzofurylphenyl group, a dibenzothiophenylphenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a spiro-bifluorenyl group, a benzonaphthofuryl group, and a benzonaphthothiophenyl group, each of which is substituted or unsubstituted; R.sup.Y1 to R.sup.Y8 are present individually without forming a ring, or any adjacent two of R.sup.Y1 to R.sup.Y8 joined to form a ring A, and the ring A is a substituted or unsubstituted benzene ring; L.sup.Y1, L.sup.Y2, L.sup.Y3, L.sup.Y4, L.sup.Y5 and L.sup.Y6 are each independently selected from a bond, a phenylene group, a biphenylene group, and a naphthylene group.

8. The organic material composition according to claim 1, wherein the compound having a structure represented by Formula 2 is selected from the compounds shown as below: ##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## ##STR00227## ##STR00228## ##STR00229## ##STR00230## ##STR00231## ##STR00232## ##STR00233## ##STR00234## ##STR00235## ##STR00236## ##STR00237## ##STR00238## ##STR00239## ##STR00240## and the compound having a structure represented by Formula 1 and the compound having a structure represented by Formula 2 have a weight ratio of 1:9 to 9:1.

9. The organic material composition according to claim 8, wherein the compound having a structure represented by Formula 1 and the compound having a structure represented by Formula 2 have a weight ratio of 4:6 to 6:4.

10. An organic electroluminescence material, wherein the organic electroluminescence material comprises the organic material composition according to claim 1.

11. An application of the organic material composition according to claim 1 in preparation of an optical element.

12. An organic electroluminescence element, wherein the organic electroluminescence element comprises an anode, a cathode and an organic layer disposed between the anode and the cathode; and the organic layer comprises the organic material composition according to claim 1.

13. An electronic device, wherein the electronic device comprises the organic electroluminescence element according to claim 12.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0096] The FIGURE is a schematic diagram of the structure of the organic electroluminescence element provided by the application example of the present invention, wherein 1 is an anode, 2 is a hole injection layer, 3 is a hole transport layer, 4 is an emitting layer, 5 is an electron transport layer, 6 is an electron injection layer, and 7 is a cathode.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0097] 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 Example of Compound of Formula 1

[0098] ##STR00111## ##STR00112##

[0099] Synthesis of M-6B: In a three-necked bottle of 25 milliliters (mL), M-6A (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 M-6B (1.34 g, 49% yield).

[0100] Synthesis of M-6B′: 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 M-6B′ (1.7 g, 64% yield).

[0101] Synthesis of M-6C: In a three-necked bottle of 50 mL, M-6B (10 mmol), M-6B′ (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 M-6C (3.06 g, 92% yield).

[0102] Synthesis of M-6D: In a three-necked bottle of 50 mL, M-6C (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 M-6D (1.8 g, 50% yield).

[0103] Synthesis of M-6E: In a three-necked bottle of 25 mL, M-6D (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 M-6E (0.24 g, 73% yield).

[0104] Synthesis of compound 1′: In a three-necked bottle of 25 mL, nitrogen gas was purged, and then M6-E (1 mmol), compound 1′-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, the organic layer was extracted by ethyl acetate and H.sub.2O, the extracted organic layer was dried by MgSO.sub.4, 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 1′ (0.50 g, 71% yield).

[0105] 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.

##STR00113##

[0106] Synthesis of 1F: In a three-necked bottle of 50 mL, M-6E (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 1F (3.24 g, 77% yield).

[0107] Synthesis of 2′: In a two-necked round-bottom flask 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 1F (0.01 mol), 2′G (0.01 mol), potassium carbonate (0.013 mol), tetrakis(triphenylphosphine)palladium (0.5 mmol), toluene (10 mL), and water (4 mL) were separately added, nitrogen gas was purged for three times, and heated to 85° C. to react for 10 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 2′ (4.44 g, 63% yield).

[0108] 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.

[0109] 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 (%) [00114] [00115] [00116] 62 [00117] [00118] [00119] 60 [00120] [00121] [00122] 61 [00123] [00124] [00125] 64 [00126] [00127] [00128] 68 [00129] [00130] [00131] 62 [00132] [00133] [00134] 66

TABLE-US-00002 TABLE 2 HRMS (ESI) Elemental analysis m/z [M + H].sup.+ Compound Calcd. Found Calcd. Found 3′ C, 85.69; H, 4.31; C, 85.75; H, 4.29; 560.20 561.11 N, 9.99 N, 9.96 4′ C, 81.96; H, 4.38; C, 81.91; H, 4.40; 644.20 645.30 N, 8.69; S, 4.97 N, 8.71; S, 4.98 5′ C, 84.73; H, 4.87; C, 84.70; H, 4.85; 538.22 539.31 N, 10.40 N, 10.45 6′ C, 85.96; H, 5.13; C, 86.01; H, 5.10; 628.26 629.33 N, 8.91 N, 8.89 7′ C, 89.32; H, 4.56; C, 89.35; H, 4.58; 685.83 686.76 N, 6.13 N, 6.08 8′ C, 88.42; H, 4.55; C, 88.43; H, 4.58; 597.72 598.55 N, 7.03 N, 6.99 9′ C, 88.23; H, 5.20; C, 88.27; H, 5.21; 639.80 640.69 N, 6.57 N, 6.52

Preparation Example of Compound of Formula 2

[0110] ##STR00135##

[0111] Synthesis of compound H1: In a two-necked round-bottom flask 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 H1-A (1 mmol, CAS1198396-40-5), H1-B (1 mmol), potassium carbonate (K.sub.2CO.sub.3, 1.5 mmol), ethanol (3 mL), water (3 mL), toluene (10 mL) and tetrakis(triphenylphosphine)palladium (Pd(PPh.sub.3).sub.4, 0.05 mmol) were separately added, and heated to 60° C. to react for 12 h. After the reaction ended, the reaction mixture was cooled to room temperature, quenched by water, extracted by methylene dichloride (3×20 mL), 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 H1 (0.46 g, 73% yield).

[0112] Anal. Calcd. C46H.sub.33N.sub.3: C, 88.01; H, 5.30; N, 6.69. Found: C, 88.06; H, 5.32; N, 6.62. HRMS (ESI) m/z [M+H].sup.+: Calcd.: 627.27. Found: 628.21.

##STR00136##

[0113] Synthesis of compound H4: In a two-necked round-bottom flask of 50 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 H4-A (14.1 mmol, CAS2095370-50-4), H4-B (18.3 mmol), tetrakis(triphenylphosphine)palladium (0.7 mmol), potassium carbonate (28.2 mmol), toluene of 42 mL, ethanol of 10 mL and distilled water of 14 mL and were separately added, and the mixture was stirred at 140° C. for 8 h. After the reaction ended, the reaction mixture was added dropwise into methanol to give a solid. The solid was filtered and purified by column chromatography (ethyl acetate:n-hexane=1:10 (volume ratio)), to obtain compound H4 (5.8 g, 75% yield).

[0114] Compounds H2 and H3 were prepared by the above-mentioned preparation method of compound H1, and compounds H5 to H7 were prepared by the above-mentioned preparation method of compound H4 using the Material 1 and Material 2 as raw materials, as shown in Table 3. The structure and characteristic data of the products are shown in Table 4.

TABLE-US-00003 TABLE 3 Material 1 Material 2 Product Yield % [00137] [00138] [00139] 70 [00140] [00141] [00142] 68 [00143] [00144] [00145] 75 [00146] [00147] [00148] 78 [00149] [00150] [00151] 75 [00152] [00153] [00154] 76

TABLE-US-00004 TABLE 4 HRMS (ESI) Elemental analysis m/z [M + H].sup.+ Compound Calcd. Found Calcd. Found H2 C, 85.54; H, 4.38; C, 85.56; H, 4.40; 575.20 576.11 N, 7.30; N, 7.27; H3 C, 87.00; H, 4.61; C, 86.97; H, 4.60; 524.19 525.28 N, 5.34; N, 5.37; H4 C, 85.23; H, 4.22; C, 85.40; H, 4.24; 549.63 550.68 N, 7.65; N, 7.46; H5 C, 85.23; H, 4.22; C, 85.41; H, 4.25; 549.63 550.71 N, 7.65; N, 7.44; H6 C, 83.88; H, 4.09; C, 83.92; H, 4.11; 615.75 616.48 N, 6.82; S, 5.21; N, 6.75; S, 5.22 H7 C, 86.38; H, 4.35; C, 86.40; H, 4.37; 625.73 626.71 N, 6.72; N, 6.68;

Element Examples

[0115] An organic electroluminescence element (such as OLED) having a structure shown in the FIGURE with the following layer structure was provided: base (indium tin oxide (ITO, as an anode 1) coated glass substrate)/hole injection layer 2 (HIL)/hole transport layer 3 (HTL)/emitting layer 4 (EML)/electron transport layer 5 (ETL)/electron injection layer 6 (EIL), and the cathode 7 at last.

[0116] The materials needed to prepare OLED are listed below:

##STR00155##

[0117] The above-mentioned organic electroluminescence elements were prepared by the following steps:

[0118] (1) Cleaning the substrate: a glass substrate coated with transparent ITO layer (the anode 1) 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.

[0119] (2) Depositing organic emitting functional layers:

[0120] The glass substrate with the anode 1 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 HAT(CN).sub.6 and HT (mass ratio of HAT(CN).sub.6 and HT is 3:97) was deposited on the anode 1 in vacuum to form a hole injection layer 2, in which the deposited thickness was 10 nanometers (nm).

[0121] A hole transport layer 3 was deposited on the hole injection layer 2, in which the deposited thickness was 80 nm.

[0122] An emitting layer 4 was deposited on the hole transport layer 3. Specifically, the preparation method was: the light-emitting host material and a guest material were co-deposited in vacuum, in which the total deposited thickness was 30 nm.

[0123] An electron transport layer 5 was deposited on the emitting layer 4. Specifically, the preparation method was: BPhen and LiQ were co-deposited in vacuum, in which the total deposited thickness was 30 nm.

[0124] An electron injection layer 6 was deposited on the electron transport layer 5, in which the total deposited thickness was 1 nm.

[0125] Al (as cathode 7) was deposited on the electron injection layer 6, in which the deposited thickness was 80 nm.

[0126] The materials (mat.) of each layer in the element and parameters such as thickness (thk.) of Element Examples 1 to 13 (E1 to E13) and Comparative Element Examples 1 to 13 (CE1 to CE13) are shown in Table 5.

TABLE-US-00005 TABLE 5 HIL HTL EML ETL EIL Cathode No. mat./thk. mat./thk. mat./thk. mat./thk. mat./thk. mat./thk. E1 HAT(CN).sub.6:HT HT/ compound 1′:compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H1:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio47.5:47.5:5)/ 30 nm 30 nm E2 HAT(CN).sub.6:HT HT/ compound 2′:compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H1:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio47.5:47.5:5)/ 30 nm 30 nm E3 HAT(CN).sub.6:HT HT/ compound 3′:compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H1:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio47.5:47.5:5)/ 30 nm 30 nm E4 HAT(CN).sub.6:HT HT/ compound 4′:compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H1:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio47.5:47.5:5)/ 30 nm 30 nm E5 HAT(CN).sub.6:HT HT/ compound 5′:compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H2:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio47.5:47.5:5)/ 30 nm 30 nm E6 HAT(CN).sub.6:HT HT/ compound 6′:compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H2:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio47.5:47.5:5)/ 30 nm 30 nm E7 HAT(CN).sub.6:HT HT/ compound 6′:compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H3:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio47.5:47.5:5)/ 30 nm 30 nm E8 HAT(CN).sub.6:HT HT/ compound 1′:compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H4:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio47.5:47.5:5)/ 30 nm 30 nm E9 HAT(CN).sub.6:HT HT/ compound 1′:compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H5:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio47.5:47.5:5)/ 30 nm 30 nm E10 HAT(CN).sub.6:HT HT/ compound 1′:compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H6:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio47.5:47.5:5)/ 30 nm 30 nm E11 HAT(CN).sub.6:HT HT/ compound 1′:compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H7:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio47.5:47.5:5)/ 30 nm 30 nm E12 HAT(CN).sub.6:HT HT/ compound 1′:compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H1:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio 17:2:1)/ 30 nm 30 nm E13 HAT(CN).sub.6:HT HT/ compound 1′:compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H1:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio38:57:5)/ 30 nm 30 nm CE1 HAT(CN).sub.6:HT HT/ compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H2:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio95:5)/ 30 nm 30 nm CE2 HAT(CN).sub.6:HT HT/ compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm 5′:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio95:5)/ 30 nm 30 nm CE3 HAT(CN).sub.6:HT HT/ compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H1:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio95:5)/ 30 nm 30 nm CE4 HAT(CN).sub.6:HT HT/ compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm 1′:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio95:5)/ 30 nm 30 nm CE5 HAT(CN).sub.6:HT HT/ compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm 2′:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio95:5)/ 30 nm 30 nm CE6 HAT(CN).sub.6:HT HT/ compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm 3′:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio95:5)/ 30 nm 30 nm CE7 HAT(CN).sub.6:HT HT/ compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm 4′:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio95:5)/ 30 nm 30 nm CE8 HAT(CN).sub.6:HT HT/ compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm 6′:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio95:5)/ 30 nm 30 nm CE9 HAT(CN).sub.6:HT HT/ compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H3:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio95:5)/ 30 nm 30 nm CE10 HAT(CN).sub.6:HT HT/ compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H4:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio95:5)/ 30 nm 30 nm CE11 HAT(CN).sub.6:HT HT/ compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H5:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio95:5)/ 30 nm 30 nm CE12 HAT(CN).sub.6:HT HT/ compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H6:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio95:5)/ 30 nm 30 nm CE13 HAT(CN).sub.6:HT HT/ compound BPhen:LiQ LiQ/ Al/ (mass ratio3:97)/ 80 nm H7:(piq).sub.2Ir(acac) (mass ratio1:1)/ 1 nm 80 nm 10 nm (mass ratio95:5)/ 30 nm 30 nm

[0127] Characteristic Tests of Elements:

[0128] Instruments: the characteristics such as current, voltage, luminance, emission spectrum and the like of the elements of the above Element Examples 1 to 13 and Comparative Element Examples 1 to 13 were synchronously tested by PR 650 SpectraScan Colorimeter and Keithley K 2400 SourceMeter;

[0129] Conditions for testing electrooptical characteristics: a current density of 10 milliamperes/square centimeter (mA/cm.sup.2) under room temperature;

[0130] Service life test: tested with a current density of 20 mA/cm.sup.2 under room temperature, and the time period recorded when the luminance of the tested element was reduced to 980 of the original luminance (in hour).

[0131] The test results of the elements are shown in Table 6.

TABLE-US-00006 TABLE 6 Driving Current Service voltage efficiency life No. (V) (Cd/A) (h) E1 3.98 17 210 E2 3.88 19 232 E3 3.97 16 195 E4 4.04 17 205 E5 4.07 17 190 E6 4.01 16 198 E7 4.05 17 183 E8 3.00 30 268 E9 3.35 28 250 E10 3.46 29 244 E11 3.92 19 226 E12 4.01 16 196 E13 3.98 17 203 CE1 4.45 12 85 CE2 4.41 10 89 CE3 4.40 14 74 CE4 4.43 9 80 CE5 3.90 13 75 CE6 4.01 15 90 CE7 3.80 11 40 CE8 4.44 13 88 CE9 4.46 10 76 CE10 4.40 11 78 CE11 4.43 13 76 CE12 4.50 16 69 CE13 4.34 10 89

[0132] From Table 6, it is clear that the organic material composition of the present invention obviously prolongs the service life of the element. When the organic material composition is used as the material of an organic functional layer, the element has a lower driving voltage (4.07 voltages (V) or lower), a higher current efficiency (16 Candelas/Ampere (Cd/A) or more) and a longer service life (190 h or more).

[0133] By comparison with Element Examples 1-13 and Element Comparative Examples 1-13, it can be found that the components comprised in the organic material composition of the present invention have synergistic effect in lowering driving voltage, enhancing current efficiency and prolonging service life.

[0134] The applicant claims herein that even though the organic material composition of the present invention and the applications thereof 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.