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, characterized in that 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): ##STR00400## 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 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group; ##STR00401## Ar.sup.W1, Ar .sup.W2 and Ar.sup.W3 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group; L.sup.W1, L.sup.W2 and L.sup.W3 are each independently selected from a bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group.

2. The organic material composition as claimed in claim 1, characterized in that, in Formula (1), at least one of Ar.sup.1 to Ar.sup.4 is a group represented by Formula (a): ##STR00402## 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, 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.X1-R.sup.X5 are present individually without forming a ring, or any adjacent two of R.sup.X1-R.sup.X5 joined to form a ring A, and the ring A is a benzene ring.

3. The organic material composition as claimed in claim 2, characterized in that the 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; in the 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; 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, and a substituted or unsubstituted biphenylene group.

4. The organic material composition as claimed in claim 1, characterized in that the compound having a structure represented by Formula (1) is selected from the following compounds: ##STR00403## ##STR00404## ##STR00405## ##STR00406## ##STR00407## ##STR00408## ##STR00409## ##STR00410## ##STR00411## ##STR00412## ##STR00413## ##STR00414## ##STR00415## ##STR00416## ##STR00417## ##STR00418## ##STR00419## ##STR00420## ##STR00421## ##STR00422## ##STR00423## ##STR00424## ##STR00425## ##STR00426## ##STR00427## ##STR00428## ##STR00429## ##STR00430## ##STR00431## ##STR00432## ##STR00433## ##STR00434## ##STR00435## ##STR00436## ##STR00437## ##STR00438## ##STR00439## ##STR00440## ##STR00441## ##STR00442## ##STR00443## ##STR00444## ##STR00445## ##STR00446## ##STR00447## ##STR00448## ##STR00449## ##STR00450## ##STR00451## ##STR00452## ##STR00453## ##STR00454## ##STR00455## ##STR00456## ##STR00457## ##STR00458## ##STR00459## ##STR00460## ##STR00461## ##STR00462## ##STR00463## ##STR00464## ##STR00465## ##STR00466## ##STR00467## ##STR00468## ##STR00469## ##STR00470## ##STR00471## ##STR00472## ##STR00473## ##STR00474## ##STR00475## ##STR00476## ##STR00477## ##STR00478## ##STR00479## ##STR00480## ##STR00481## ##STR00482## ##STR00483## ##STR00484## ##STR00485## ##STR00486## ##STR00487## ##STR00488## ##STR00489## ##STR00490## ##STR00491## ##STR00492## ##STR00493## ##STR00494## ##STR00495## ##STR00496## ##STR00497## ##STR00498## ##STR00499## ##STR00500## ##STR00501## ##STR00502## ##STR00503## ##STR00504## ##STR00505## ##STR00506## ##STR00507## ##STR00508## ##STR00509## ##STR00510## ##STR00511## ##STR00512## ##STR00513## ##STR00514## ##STR00515## ##STR00516## ##STR00517## ##STR00518## ##STR00519## ##STR00520## ##STR00521## ##STR00522## ##STR00523## ##STR00524## ##STR00525## ##STR00526## ##STR00527## ##STR00528## ##STR00529## ##STR00530## ##STR00531## ##STR00532## ##STR00533## ##STR00534## ##STR00535## ##STR00536## ##STR00537## ##STR00538## ##STR00539## ##STR00540## ##STR00541## ##STR00542## ##STR00543## ##STR00544## ##STR00545## ##STR00546## ##STR00547## ##STR00548## ##STR00549## ##STR00550## ##STR00551## ##STR00552## ##STR00553## ##STR00554## ##STR00555## ##STR00556## ##STR00557## ##STR00558## ##STR00559## ##STR00560## ##STR00561## ##STR00562## ##STR00563## ##STR00564## ##STR00565## ##STR00566## ##STR00567## ##STR00568## ##STR00569## ##STR00570## ##STR00571## ##STR00572## ##STR00573## ##STR00574## ##STR00575## ##STR00576## ##STR00577## ##STR00578## ##STR00579## ##STR00580## ##STR00581## ##STR00582## ##STR00583## ##STR00584## ##STR00585## ##STR00586## ##STR00587## ##STR00588## ##STR00589## ##STR00590## ##STR00591## ##STR00592## ##STR00593## ##STR00594## ##STR00595## ##STR00596## ##STR00597## ##STR00598## ##STR00599## ##STR00600## ##STR00601## ##STR00602## ##STR00603## ##STR00604## ##STR00605## ##STR00606## ##STR00607## ##STR00608## ; wherein D represents deuterium.

5. The organic material composition as claimed in claim 1, characterized in that, in Formula (2), Ar.sup.W1, Ar.sup.W2 and Ar.sup.W3 are each independently 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 triphenylenylene group, a pyridyl group, and a group represented by Formula (b-1): ##STR00609## wherein W is selected from O, S, CR.sup.W1R.sup.W2 and NR.sup.W, in which R.sup.W is —L.sup.WR.sup.W3; when any one or two or three of Ar.sup.W1, Ar.sup.W2 and Ar.sup.W3 are selected from Formula (b-1), any one of R.sup.10 to R.sup.17, R.sup.W1, R.sup.W2 and R.sup.W3 is connected to L.sup.W1, L.sup.W2 or L.sup.W3 by chemical bonding; when Formula (2) comprises multiple groups represented by Formula (b-1), the groups represented by Formula (b-1) are the same or different; R.sup.10 to R.sup.17, R.sup.W1, R.sup.W2 and R.sup.W3 are each independently selected from a bond, hydrogen, deuterium, halogen, a cyano group, a substituted or unsubstituted C1-C30 alkyl group, 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.10 to R.sup.17 are present individually without forming a ring, or any adjacent two of R.sup.10 to R.sup.17 joined to form a ring B, and the ring B is a substituted or unsubstituted C6-C30 aromatic ring; L.sup.W is selected from a bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group.

6. The organic material composition as claimed in claim 5, characterized in that the Formula (b-1) is selected from the structures represented as below: ##STR00610## ##STR00611## ##STR00612## ##STR00613## ##STR00614## ##STR00615## R.sup.10 to R.sup.17 are each independently selected from hydrogen, deuterium, 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 grou, a dimethylfluorenyl group, a diphenylfluorenyl group, a spiro-bifluorenyl group, a benzonaphthofuryl group, and a benzonaphthothiophenyl group; W is selected from O, S, CR.sup.W1R.sup.W2 and NR.sup.W, in which R.sup.W is —L.sup.WR.sup.W3; R.sup.W1 to R.sup.W2 are each independently selected from hydrogen, deuterium, a methyl group, an ethyl group and a phenyl group; or, R.sup.W1 to R.sup.W2 joined to form a spiro ring by chemical bonding; R.sup.W3 is a group 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, each of which is substituted or unsubstituted; and L.sup.W is selected from a bond, a phenylene group, a biphenylene group, and a naphthylene group.

7. The organic material composition as claimed in claim 5, wherein the Formula (b-1) is selected from the groups represented as below: ##STR00616## ##STR00617## ##STR00618## ##STR00619## ##STR00620## ##STR00621## ##STR00622## ##STR00623## ##STR00624## ##STR00625## ##STR00626## ##STR00627## ##STR00628## ##STR00629## ##STR00630## ##STR00631## ##STR00632## ##STR00633## ##STR00634## ##STR00635## ##STR00636## ##STR00637## ##STR00638## ##STR00639## ##STR00640## ##STR00641## ##STR00642## ##STR00643## ##STR00644## ##STR00645## ##STR00646## ##STR00647## ##STR00648## , each of which is substituted or unsubstituted; wherein ##STR00649## represents the connection position of the group; when the above-mentioned group has one or more substituents, the substituents are each independently selected from deuterium, halogen, a cyano group, a nitro group, an unsubstituted or R′-substituted C1-C4 straight or branched alkyl group, an unsubstituted or R′-substituted C6-C20 aryl group, an unsubstituted or R′-substituted C3-C20 heteroaryl group, and an unsubstituted or R′-substituted C6-C20 arylamino group; R′ is selected from deuterium, halogen, a cyano group and a nitro group; the aryl group is selected from a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an anthryl group, a phenanthryl group, a benzophenanthryl group, a naphthylphenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group and a spiro-bifluorenyl group; the heteroaryl group is selected from a pyridyl group, a dibenzofuryl group, a dibenzothiophenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridylcarbazolyl group, a naphthylcarbazolyl group, a biphenylylcarbazolyl group, a dibenzofurylphenyl group, a dibenzothiophenylphenyl group, a benzonaphthofuryl group, a benzonaphthothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group; the alkyl group is selected from a methyl group, an ethyl group, a propyl group, a tert-butyl group, a cyclohexyl group and adamantyl.

8. The organic material composition as claimed in claim 1, characterized in that the compound having a structure represented by Formula (2) is selected from the compounds shown as below: ##STR00650## ##STR00651## ##STR00652## ##STR00653## ##STR00654## ##STR00655## ##STR00656## ##STR00657## ##STR00658## ##STR00659## ##STR00660## ##STR00661## ##STR00662## ##STR00663## ##STR00664## ##STR00665## ##STR00666## ##STR00667## ##STR00668## ##STR00669## ##STR00670## ##STR00671## ##STR00672## ##STR00673## ##STR00674## ##STR00675## ##STR00676## ##STR00677## ##STR00678## ##STR00679## ##STR00680## ##STR00681## ##STR00682## ##STR00683## ##STR00684## ##STR00685## ##STR00686## ##STR00687## ##STR00688## ##STR00689## ##STR00690## ##STR00691## ##STR00692## ##STR00693## ##STR00694## ##STR00695## ##STR00696## ##STR00697## ##STR00698## ##STR00699## ##STR00700## ##STR00701## ##STR00702## ##STR00703## ##STR00704## ##STR00705## ##STR00706## ##STR00707## ##STR00708## ##STR00709## ##STR00710## ##STR00711## ; 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 as claimed in claim 8, characterized in that 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, characterized in that the organic electroluminescence material comprises the organic material composition as claimed in claim 1.

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

12. An application of the organic electroluminescence material as claimed in claim 10 in preparation of an optical element.

13. An organic electroluminescence element, characterized in that 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 as claimed in claim 1.

14. An organic electroluminescence element, characterized in that 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 electroluminescence material as claimed in claim 10.

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

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

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0078] FIG. 1 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

[0079] 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)

##STR00346##

##STR00347##

##STR00348##

##STR00349##

##STR00350##

##STR00351##

##STR00352##

[0080] Synthesis of 1B: In a three-necked bottle of 25 milliliters (mL), 1A (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 1B (1.34 g, 49% yield).

[0081] Synthesis of 1B′: 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 1B′ (1.7 g, 64% yield).

[0082] Synthesis of 1C: In a three-necked bottle of 50 mL, 1B (10 mmol), 1B′ (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 1C (3.06 g, 92% yield).

[0083] Synthesis of 1D: In a three-necked bottle of 50 mL, 1C (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 1D (1.8 g, 50% yield).

[0084] Synthesis of 1E: In a three-necked bottle of 25 mL, 1D (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 1E (0.24 g, 73% yield).

[0085] Synthesis of 1F: In a three-necked bottle of 50 mL, 1E (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).

[0086] Synthesis of 1: 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 1F (10 mmol), 1G (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 1 (4.13 g, 69% yield).

[0087] 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.

##STR00353##

##STR00354##

##STR00355##

##STR00356##

##STR00357##

##STR00358##

##STR00359##

[0088] Synthesis of 1B″: Similar to the synthesis of 1B′, with the difference that 2-bromo-5-chlorobenzaldehyde is used to replace 2-bromo-4-chlorobenzaldehyde, to obtain 1B″ (1.60 g, 60% yield).

[0089] Synthesis of 8C: Similar to the synthesis of 1C, with the difference that 4-fluoro-2-formylbenzeneboronic acid pinacol ester is used to replace 5-fluoro-2-formylbenzeneboronic acid pinacol ester, to obtain 8C (2.13 g, 64% yield).

[0090] Synthesis of 8D: Similar to the synthesis of 1D, with the difference that 8C is used to replace 1C, to obtain 8D (3.21 g, 89% yield).

[0091] Synthesis of 8E: Similar to the synthesis of 1E, with the difference that 8D is used to replace 1D, to obtain 8E (0.16 g, 48% yield).

[0092] Synthesis of 8F: Similar to the synthesis of 1F, with the difference that 8E is used to replace 1E, to obtain 8F (4.00 g, 95% yield).

[0093] Synthesis of compound 8: Similar to the synthesis of compound 1, with the difference that 8F is used to replace 1F, and 8G is used to replace 1G, to obtain compound 8 (4.70 g, 78% yield).

[0094] 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.

[0095] 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 Material 1 Material 2 Product Yield (%) [00360] [00361]CAS2142681-84-1 [00362] 65 [00363] [00364]CAS2391956-00-4 [00365] 67 [00366] [00367]CAS1618106-98-1 [00368] 74 [00369] [00370]CAS2102445-28-1 [00371] 65 [00372] [00373]CAS1413365-66-8 [00374] 68 [00375] [00376]CAS2286234-09-9 [00377] 68 [00378] [00379]CAS 1268244-56-9 [00380] 61

TABLE-US-00002 Compound Elemental analysis HRMS (ESI) m/z [M+H].sup.+ Calcd. Found Calcd. Found 2 C, 79.85; H, 3.92; N, 13.63; C, 79.92; H, 3.91; N, 13.59; 616.20 617.26 3 C, 79.21; H, 4.70; N, 13.52; C, 79.24; H, 4.71; N, 13.48; 621.23 622.26 4 C, 82.22; H, 4.70; N, 13.08; C, 82.16; H, 4.72; N, 13.12; 642.25 643.25 5 C, 81.49; H, 4.07; N, 12.13; C, 81.53; H, 4.08; N, 12.08; 692.23 693.20 6 C, 83.46; H, 4.38; N, 12.17; C, 83.39; H, 4.40; N, 12.21; 575.21 576.24 7 C, 81.93; H, 4.09; N, 11.37; C, 81.89; H, 4.11; N, 11.40; 615.21 616.17 9 C, 79.98; H, 4.09; N, 15.92; C, 80.04; H, 4.08; N, 15.88; 615.22 616.16

[0096] Preparation Example of Compound of Formula (2)

##STR00381##

##STR00382##

##STR00383##

[0097] Synthesis of compound H1: In a three-necked bottle of 25 mL, H1-A (1 mmol), H1-B (1 mmol), Pd.sub.2(dba).sub.3 (0.05 mmol), 50% tri-tert-butylphosphine solution (0.1 mmol), NaOtBu (2.2 mmol) and toluene (10 mL) was added, and stirred under reflux for 6 h to react. After the reaction ended, the reaction mixture was cooled to room temperature, and the organic solvent was removed by evaporation under vacuum 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 (0.28 g, 48% yield).

[0098] Anal. Calcd. C.sub.48H.sub.31NO.sub.2: C, 88.18; H, 4.78; N, 2.14. Found: C, 88.24; H, 4.76; N, 2.13. HRMS (ESI) m/z [M+H].sup.+: Calcd.: 653.24. Found: 654.30.

[0099] Compounds H2 to H6 were synthesized by the same synthesis method for preparing compound H1. The raw materials and resulting products are shown in Table 3. The structure and characteristic data of the products are shown in Table 4.

TABLE-US-00003 Material 1 Material 2 Product Yield% [00384]CAS102113-98-4 [00385]CAS1239585-39-7 [00386]H2 53 [00387]CAS355832-04-1 [00388]CAS1819347-21-1 [00389]H3 51 [00390]CAS2124211-93-2 [00391]CAS 1153-85-1 [00392]H4 52

TABLE-US-00004 Compound Elemental analysis HRMS (ESI) m/z [M+H].sup.+ Calcd. Found Calcd. Found H2 C, 92.79; H, 5.24; N, 1.97; C, 92.81; H, 5.22; N, 1.97; 711.29 712.36 H3 C, 90.06; H, 5.47; N, 4.47; C, 90.01; H, 5.50; N, 4.49; 626.27 627.29 H4 C, 90.06; H, 5.47; N, 4.47; C, 90.09; H, 5.45; N, 4.46; 626.27 627.22

APPLICATION EXAMPLES

[0100] An organic electroluminescence element (such as OLED) having a structure shown in FIG. 1 with the following layer structure was provided: base (indium tin oxide (ITO, as an anode 1) coated glass substrate) / hole injection layer (HIL) 2 / hole transport layer (HTL) 3 / emitting layer (EML) 4/ electron transport layer (ETL) 5 / electron injection layer (EIL) 6, and the cathode 7 at last.

[0101] The materials needed to prepare OLED are listed below, wherein the REF-1 is comparative compound 1:

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[0102] The above-mentioned organic electroluminescence elements were prepared by the following steps: [0103] (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 ≤ 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; [0104] (2) Depositing organic emitting functional layers: [0105] 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).

[0106] A hole transport layer 3 was deposited on the hole injection layer 2, in which the deposited thickness was 80 nm.

[0107] 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.

[0108] 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.

[0109] An electron injection layer 6 was deposited on the electron transport layer 5, in which the total deposited thickness was 1 nm.

[0110] Al (as cathode 7) was deposited on the electron injection layer 6, in which the deposited thickness was 80 nm.

[0111] The materials (mat.) of each layer in the element and parameters such as thickness (thk.) of Element Examples 1 to 16 (E1 to E11) and Comparative Element Examples 1 to 3 (CE1 to CE3) are shown in Table 5.

TABLE-US-00005 No. HIL mat./ thk. HTL mat./ thk. EML mat./ thk. ETL mat./ thk. EIL mat./ thk. Catho de mat./ thk. E1 HAT(CN).sub.6 : HT (mass ratio 3:97)/ 10 nm HT/ 80 nm compound 1: compound H3: (piq).sub.2Ir(acac) (mass ratio 47.5:47.5:5)/ 30 nm BPhen: LiQ (mass ratio 1:1)/ 30 nm LiQ/ 1 nm Al/ 80 nm E2 HAT(CN).sub.6 : HT (mass ratio 3:97)/ 10 nm HT/ 80 nm compound 2: compound H4: (piq).sub.2Ir(acac) (mass ratio 47.5:47.5:5)/ 30 nm BPhen: LiQ (mass ratio 1:1)/ 30 nm LiQ/ 1 nm Al/ 80 nm E3 HAT(CN).sub.6 : HT (mass ratio 3:97)/ 10 nm HT/ 80 nm compound 3: compound H3: (piq).sub.2Ir(acac) (mass ratio 47.5:47.5:5)/ 30 nm BPhen: LiQ (mass ratio 1:1)/ 30 nm LiQ/ 1 nm Al/ 80 nm E4 HAT(CN).sub.6 : HT (mass ratio 3:97)/ 10 nm HT/ 80 nm compound 4: compound H1: (piq).sub.2Ir(acac) (mass ratio 47.5:47.5:5)/ 30 nm BPhen: LiQ (mass ratio 1:1)/ 30 nm LiQ/ 1 nm Al/ 80 nm E5 HAT(CN).sub.6 : HT (mass HT/ 80 nm compound 5: compound H2: BPhen: LiQ LiQ/ 1 nm Al/ 80 nm ratio 3:97)/ 10 nm (piq).sub.2Ir(acac) (mass ratio 47.5:47.5:5)/ 30 nm (mass ratio 1:1)/ 30 nm E6 HAT(CN).sub.6 : HT (mass ratio 3:97)/ 10 nm HT/ 80 nm compound 6: compound H4: (piq).sub.2Ir(acac) (mass ratio 47.5:47.5:5)/ 30 nm BPhen: LiQ (mass ratio 1:1)/ 30 nm LiQ/ 1 nm Al/ 80 nm E7 HAT(CN).sub.6 : HT (mass ratio 3:97)/ 10 nm HT/ 80 nm compound 7: compound H4: (piq).sub.2Ir(acac) (mass ratio 47.5:47.5:5)/ 30 nm BPhen: LiQ (mass ratio 1:1)/ 30 nm LiQ/ 1 nm Al/ 80 nm E8 HAT(CN).sub.6 : HT (mass ratio 3:97)/ 10 nm HT/ 80 nm compound 9: compound H4: (piq).sub.2Ir(acac) (mass ratio 47.5:47.5:5)/ 30 nm BPhen: LiQ (mass ratio 1:1)/ 30 nm LiQ/ 1 nm Al/ 80 nm E9 HAT(CN).sub.6 : HT (mass ratio 3:97)/ 10 nm HT/ 80 nm compound 8: compound H3: (piq).sub.2Ir(acac) (mass ratio 47.5:47.5:5)/ 30 nm BPhen: LiQ (mass ratio 1:1)/ 30 nm LiQ/ 1 nm Al/ 80 nm E10 HAT(CN).sub.6 : HT (mass ratio 3:97)/ 10 nm HT/ 80 nm compound 1: compound H3: (piq).sub.2Ir(acac) (mass ratio 57:38:5)/ 30 nm BPhen: LiQ (mass ratio 1:1)/ 30 nm LiQ/ 1 nm Al/ 80 nm E11 HAT(CN).sub.6 : HT (mass ratio 3:97)/ 10 nm HT/ 80 nm compound 1: compound H3: (piq).sub.2Ir(acac) (mass ratio 2:17:5)/ 30 nm BPhen: LiQ (mass ratio 1:1)/ 30 nm LiQ/ 1 nm Al/ 80 nm CE 1 HAT(CN).sub.6 : HT (mass ratio 3:97)/ 10 nm HT/ 80 nm compound H1: (piq).sub.2Ir(acac) (mass ratio 95:5)/ 30 nm BPhen: LiQ (mass ratio 1:1)/ 30 nm LiQ 1 nm Al/ 80 nm CE 2 HAT(CN).sub.6 : HT (mass ratio 3:97)/ 10 nm HT/ 80 nm compound 4: (piq).sub.2Ir(acac) (mass ratio 95:5)/ 30 nm BPhen: LiQ (mass ratio 1:1)/ 30 nm LiQ/ 1 nm Al/ 80 nm CE 3 HAT(CN).sub.6 : HT (mass ratio 3:97)/ 10 nm HT/ 80 nm REF-1: compound H1: (piq).sub.2Ir(acac) (mass ratio 47.5:47.5:5)/ 30 nm BPhen: LiQ (mass ratio 1:1)/ 30 nm LiQ/ 1 nm Al/ 80 nm

CHARACTERISTIC TESTS OF ELEMENTS

[0112] Instruments: the characteristics such as current, voltage, luminance, emission spectrum and the like of the elements of the above Element Examples 1 to 11 and Comparative Element Examples 1 to 3 were synchronously tested by PR 650 SpectraScan Colorimeter and Keithley K 2400 SourceMeter; [0113] Conditions for testing electrooptical characteristics: a current density of 10 milliamperes/square centimeter (mA/cm.sup.2) under room temperature; [0114] 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 98% of the original luminance (in hour).

[0115] The test results of the elements are shown in Table 6.

TABLE-US-00006 No. Driving voltage (V) Current efficiency (Cd/A) Service life (h) E1 3.85 23 165 E2 3.86 21 160 E3 3.97 21 168 E4 4.02 18 155 E5 4.07 19 150 E6 3.97 19 158 E7 4.04 20 150 E8 4.01 18 145 E9 3.89 19 150 E10 3.87 24 185 E11 3.95 19 150 CE1 4.35 12 34 CE2 4.12 17 95 CE3 4.27 15 85

[0116] From Table 6, it is clear that the organic material composition of the present invention obviously increases the current efficiency. 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 (18 Candelas/Ampere (Cd/A) or more) and a longer service life (145 h or more).

[0117] 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.