PLURALITY OF HOST MATERIALS AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME

Abstract

The present disclosure relates to a plurality of host materials comprising a first host material having a compound represented by formula 1, and a second host material having a compound represented by formula 2, and an organic electroluminescent device comprising the same. By comprising a specific combination of compounds of the present disclosure as host materials, it is possible to provide an organic electroluminescent device having long lifetime properties while having an equivalent or improved level of power efficiency compared to conventional organic electroluminescent devices.

Claims

1. A plurality of host materials comprising a first host material and a second host material, wherein the first host material comprises a compound represented by the following formula 1: ##STR00262## wherein, L.sub.1 to L.sub.3, each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; Ar.sub.1 represents a substituted or unsubstituted nitrogen-containing (3- to 30-membered)heteroaryl; Ar.sub.2 and Ar.sub.3,each independently, represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; and the second host material comprises a compound represented by the following formula 2: ##STR00263## wherein, Y.sub.1 represents O, S, CR.sub.11R.sub.12, or NR.sub.13; R.sub.11 and R.sub.12, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or R.sub.11 and R.sub.12 may be linked to each other to form a spiro ring; R.sub.13, each independently, represents -L-(Ar).sub.d, hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; R.sub.1, each independently, represents -L-(Ar).sub.d, hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or at least two of adjacent R.sub.1's may be linked to each other to form a ring(s); R.sub.2 and R.sub.3, each independently, represent -L-(Ar).sub.d, hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; with the proviso that at least one of R.sub.13, R.sub.1, R.sub.2 and R.sub.3 represents -L-(Ar).sub.d; L represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; Ar, each independently, represents a substituted or unsubstituted nitrogen-containing (3-to 30-membered)heteroaryl; a, c and d, each independently, represent an integer of 1 to 4; where a, c and d, each independently, are an integer of 2 or more, each of R.sub.1, each of R.sub.3, and each of Ar may be the same or different; and b, independently, represents an integer of 1 or 2; where b is an integer of 2, each of R.sub.2 may be the same or different.

2. The plurality of host materials according to claim 1, wherein the substituents of the substituted alkyl, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, the substituted cycloalkyl, the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted mono- or di-alkylamino, the substituted mono- or di-arylamino, and the substituted alkylarylamino, each independently, are at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (C3-C30)cycloalkenyl; a (3- to 7-membered)heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl(s); a (C6-C30)aryl unsubstituted or substituted with at least one of a (C1-C30)alkyl(s) and a (3- to 30-membered)heteroaryl(s); a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; an amino; a mono- or di-(C1-C30)alkylamino; a mono- or di-(C6-C30)arylamino; a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl.

3. The plurality of host materials according to claim 1, wherein the formula 1 is represented by at least one of the following formulas 1-1 to 1-11: ##STR00264## ##STR00265## ##STR00266## wherein, Ar.sub.2, Ar.sub.3, and L.sub.1 to L.sub.3 are as defined in claim 1; Y represents O, S, CR.sub.4R.sub.5, or NR.sub.6; T.sub.1 to T.sub.13, and X.sub.1 to X.sub.12, each independently, represent N or CV.sub.1; R.sub.4 to R.sub.11, and V.sub.1, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or R.sub.4 and R.sub.5 may be linked to each other to form a ring(s); or at least two of adjacent R.sub.7 to R.sub.11 may be linked to each other to form a ring(s); or at least two of adjacent V.sub.1's may be linked to each other to form a ring(s); Ar.sub.5 and Ar.sub.8, each independently, represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; g, h, i and k, each independently, represent an integer of 1 to 4; where g, h, i and k, each independently, are an integer of 2 or more, each of R.sub.7, each of R.sub.8, each of R.sub.9 and each of R.sub.11 may be the same or different; and j represents an integer of 1 or 2; where j represents an integer of 2, each of R.sub.10 may be the same or different.

4. The plurality of host materials according to claim 1, wherein the formula 2 is represented by at least one of the following formulas 2-1 to 2-9: ##STR00267## ##STR00268## wherein, Y.sub.1, L, Ar, and a to d are as defined in claim 1; m represents an integer of 1; f represents an integer of 1 to 3, where f represents an integer of 2 or more, each of R.sub.3 may be the same or different; and R.sub.1 to R.sub.3, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.

5. The plurality of host materials according to claim 1, wherein the compound represented by formula 1 is at least one selected from the group consisting of the following compounds: ##STR00269## ##STR00270## ##STR00271## ##STR00272## ##STR00273## ##STR00274## ##STR00275## ##STR00276## ##STR00277## ##STR00278## ##STR00279## ##STR00280## ##STR00281## ##STR00282## ##STR00283## ##STR00284## ##STR00285## ##STR00286## ##STR00287## ##STR00288## ##STR00289## ##STR00290## ##STR00291## ##STR00292## ##STR00293## ##STR00294## ##STR00295## ##STR00296## ##STR00297## ##STR00298##

6. The plurality of host materials according to claim 1, wherein the compound represented by formula 2 is at least one selected from the group consisting of the following compounds: ##STR00299## ##STR00300## ##STR00301## ##STR00302## ##STR00303## ##STR00304## ##STR00305## ##STR00306## ##STR00307## ##STR00308## ##STR00309## ##STR00310## ##STR00311## ##STR00312## ##STR00313## ##STR00314## ##STR00315## ##STR00316## ##STR00317## ##STR00318## ##STR00319## ##STR00320## ##STR00321## ##STR00322## ##STR00323## ##STR00324## ##STR00325## ##STR00326## ##STR00327## ##STR00328## ##STR00329## ##STR00330## ##STR00331## ##STR00332## ##STR00333## ##STR00334## ##STR00335## ##STR00336## ##STR00337## ##STR00338## ##STR00339## ##STR00340## ##STR00341## ##STR00342## ##STR00343## ##STR00344## ##STR00345## ##STR00346## ##STR00347## ##STR00348## ##STR00349## ##STR00350## ##STR00351## ##STR00352## ##STR00353## ##STR00354## ##STR00355## ##STR00356## ##STR00357## ##STR00358## ##STR00359## ##STR00360## ##STR00361## ##STR00362## ##STR00363## ##STR00364## ##STR00365## ##STR00366## ##STR00367## ##STR00368## ##STR00369## ##STR00370## ##STR00371## ##STR00372## ##STR00373## ##STR00374## ##STR00375## ##STR00376## ##STR00377## ##STR00378## ##STR00379## ##STR00380## ##STR00381## ##STR00382## ##STR00383## ##STR00384## ##STR00385## ##STR00386## ##STR00387## ##STR00388## ##STR00389## ##STR00390## ##STR00391## ##STR00392## ##STR00393## ##STR00394## ##STR00395## ##STR00396## ##STR00397## ##STR00398## ##STR00399## ##STR00400## ##STR00401## ##STR00402## ##STR00403## ##STR00404## ##STR00405## ##STR00406## ##STR00407## ##STR00408## ##STR00409## ##STR00410## ##STR00411## ##STR00412## ##STR00413##

7. An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein at least one layer of the light-emitting layers comprises the plurality of host materials according to claim 1.

Description

EXAMPLE 1: PREPARATION OF COMPOUND H-1-38

[0084] ##STR00228##

[0085] 5.0 g of compound A (11.2 mmol), 3.0 g of N-phenyl-[1,1′-biphenyl]-4-amine (12.3 mmol), 0.5 g of Pd.sub.2(dba).sub.3 (0.56 mmol), 0.46 g of s-phos (1.12 mmol), and 2.7 g of NaOtBu (28 mmol) were added to 60 mL of toluene, and the mixture was stirred under reflux for 6 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and stirred at room temperature, and then MeOH was added thereto. The resultant solid was filtered under reduced pressure, and then separated by column chromatography with MC/Hex to obtain 2.3 g of compound H-1-38 (yield: 34%).

TABLE-US-00001 MW M.P. H-1-38 610.8 132° C.

[0086] EXAMPLE 2: PREPARATION OF COMPOUND H-1-58

##STR00229##

[0087] 5.0 g of compound B (15.2 mmol), 5.4 g of 4-bromo-N,N-diphenylaniline (16.7 mmol), 0.7 g of Pd.sub.2(dba).sub.3 (0.76 mmol), 0.6 g of s-phos (1.52 mmol), and 2.9 g of NaOtBu (30.4 mmol) were added to 80 mL of o-xylene, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, the mixture was cooled to room temperature, and stirred at room temperature, and then MeOH was added thereto. The resultant solid was filtered under reduced pressure, and then separated by column chromatography with MC/Hex to obtain 4.0 g of compound H-1-58 (yield: 46%).

TABLE-US-00002 MW M.P. H-1-58 573.7 317° C.

[0088] EXAMPLE 3: PREPARATION OF COMPOUND C-230

##STR00230##

1) Synthesis of Compound 3

[0089] In a flask, 30 g of compound 1 (94.19 mmol), 13.1 g of compound 2 (94.19 mmol), 5.4 g of tetrakis(triphenylphosphine)palladium(0) (4.709 mmol), and 39 g of potassium carbonate (282.5 mmol) were dissolved in 580 mL of toluene, 145 mL, of ethanol and 145 mL of water, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, the mixture was cooled to room temperature, and extracted with ethyl acetate, and then separated by column chromatography to obtain 18.5 g of compound 3 (yield: 68%).

2) Synthesis of Compound 4

[0090] 18.5 g of compound 3 (64.52 mmol) and 112 g of pyridine hydrochloride (967.9 mmol) were added to a flask, and the mixture was stirred under reflux at 230° C. for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, and extracted with dimethyl chloride. The extracted organic layer was distilled under reduced pressure, and hexane was added dropwise. The resultant was filtered to obtain 14.8 g of compound 4 (yield: 84%).

3) Synthesis of Compound 5

[0091] 14.8 g of compound 4 (54.27 mmol), 3.75 g of potassium carbonate (27.13 mmol), and 360 mL of dimethylformamide were added to a flask, and the mixture was stirred under reflux for 1 hour. After completion of the reaction, the mixture was cooled to room temperature, and water was added dropwise. The resultant was filtered to obtain 13 g of compound 5 (yield: 94%).

4) Synthesis of Compound 6

[0092] 10 g of compound 5 (39.57 mmol), 12 g of bis(pinacolato)diboron (47.48 mmol), 1.4 g of tris(dibenzylideneacetone)dipalladium(0) (1.582 mmol), 1.3 g of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (3.165 mmol), 11.6 g of potassium acetate (118.7 mmol), and 200 mL of 1,4-dioxane were added to a flask, and the mixture was stirred under reflux for 3 hours. After completion of the reaction, the mixture was extracted with ethyl acetate, and then separated by column chromatography to obtain 7.8 g of compound 6 (yield: 54%).

5) Synthesis of Compound C-230

[0093] 4.5 g of compound 6 (13.07 mmol), 5 g of compound 7 (13.07 mmol), 0.75 g of tetrakis(triphenylphosphine)palladium(0) (0.653 mmol), 5.4 g of potassium carbonate (39.22 mmol), 80 mL of toluene, 20 mL of ethanol, and 20 mL of water were added to a flask, and the mixture was stirred under reflux for 2 hours. After completion of the reaction, the mixture was cooled to room temperature, and methanol was added dropwise. The resultant was filtered, and dissolved in dimethyl chloride, and then separated by column chromatography to obtain 3.7 g of compound C-230 (yield: 53%).

TABLE-US-00003 MW M.P. C-230 525.6 272° C.

EXAMPLE 4: PREPARATION OF COMPOUND C-167

[0094] ##STR00231##

[0095] In a flask, 5 g of compound 4-1 (19.03 mmol), 9.1 g of compound 4-2 (20.94 mmol), 0.88 g of tris(dibenzylideneacetone)dipalladium(0) (0.97 mmol), 0.79 g of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.93 mmol), and 4.63 g of sodium tert-butoxide (48.3 mmol) were dissolved in 100 mL of o-xylene, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, the mixture was extracted with ethyl acetate, and then separated by column chromatography to obtain 5 g of compound C-167 (yield: 50%).

TABLE-US-00004 MW M.P. C-167 525.61 252.6° C.

EXAMPLE 5: PREPARATION OF COMPOUND C-489

[0096] ##STR00232##

[0097] 5.0 g of compound 5-1 (13.9 mmol), 6.1 g of 2-(4-bromonaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine (13.9 mmol), 0.8 g of tetrakis(triphenylphosphine)palladium(0) (0.7 mmol), 3.9 g of potassium carbonate (27.8 mmol), 30 mL of toluene, 10 mL of ethanol and 14 mL of distilled water were added to a reaction vessel, and the mixture was stirred at 130° C. for 5 hours. After completion of the reaction, the precipitated solid was washed with distilled water and methanol, and then purified by column chromatography to obtain 3.6 g of compound C-489 (yield: 44%).

TABLE-US-00005 MW M.P. C-489 591.7 282.5° C.

EXAMPLE 6: PREPARATION OF COMPOUND C-585

[0098] ##STR00233##

[0099] 4.0 g of compound 6-1 (14.9 mmol), 7.1 g of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (16.4 mmol), 0.7 g of tris(dibenzylideneacetone)dipalladium(0) (0.74 mmol), 0.6 g of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (s-phos) (1.49 mmol), 3.5 g of sodium tert-butoxide (37.3 mmol), and 80 mL of o-xylene were added to a reaction vessel, and the mixture was stirred at 165° C. for 5 hours. After completion of the reaction, the mixture was cooled to room temperature, and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate, and the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 4.2 g of compound C-585 (yield: 81%).

TABLE-US-00006 MW M.P. C-585 541.7 283° C.

EXAMPLE 7: PREPARATION OF COMPOUND C-174

[0100] ##STR00234##

[0101] 6.0 g of 1-chloro naphtho[1,2-b]benzofuran (23.7 mmol), 11.4 g of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (26.1 mmol), 1.1 g of tris(dibenzylideneacetone)dipalladium(0) (1.2 mmol), 0.98 g of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (s-phos) (2.4 mmol), 12.6 g of potassium phosphate (59.3 mmol) and 120 mL of o-xylene were added to a reaction vessel, and the mixture was stirred at 165° C. for 5 hours. After completion of the reaction, the mixture was cooled to room temperature, and an organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate, and the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 4.0 g of compound C-174 (yield: 32%).

TABLE-US-00007 MW M.P. C-174 525.6 244° C.

EXAMPLE 8: PREPARATION OF COMPOUND C-520

[0102] ##STR00235##

[0103] 4.23 g of 2-(11,11-dimethyl-11H-benzo[a]fluoren-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (11.4 mmol), 5.04 g of 2-chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (13.7 mmol), 0.66 g of tetrakis(triphenylphosphine)palladium(0) (0.57 mmol), 3.15 g of potassium carbonate (22.8 mmol), 35 mL of toluene, 7 mL of ethanol, and 11 mL of distilled water were added to a reaction vessel, and the mixture was stirred at 130° C. for 15 hours. After completion of the reaction, the precipitated solid was washed with distilled water and methanol, and then separated by column chromatography to obtain 4.5 g of compound C-520 (yield: 69%).

TABLE-US-00008 MW M.P. C-520 575.7 293° C.

EXAMPLE 9: PREPARATION OF COMPOUND C-584

[0104] ##STR00236##

1) Synthesis of Compound 1-1

[0105] 37 g of compound C (205.05 mmol), 30 g of 2-bromo-6-chlorobenzaldehyde (136.7 mmol), 4.7 g of tetrakis(triphenylphosphine)palladium(0) (4.1 mmol), 47.2 g of potassium carbonate (341.75 mmol), 400 mL of tetrahydrofuran, and 100 mL of distilled water were added to a reaction vessel, and the mixture was stirred at 100° C. for 4 hours. After completion of the reaction, the reaction mixture was washed with distilled water, and an organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 35 g of compound 1-1 (yield: 94%).

2) Synthesis of Compound 1-2

[0106] 35 g of compound 1-1 (128.32 mmol), 66 g of (methoxymethyl)triphenylphosphonium chloride (192.48 mmol) and 350 mL of tetrahydrofuran were added to a reaction vessel, and then 193 mL of 1 M potassium tert-butoxide was added dropwise at 0° C. After completion of the dropwise addition, the reaction temperature was gradually raised to room temperature, and the mixture was further stirred for 2 hours. After completion of the reaction, an organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 31 g of compound 1-2 (yield: 80%).

3) Synthesis of Compound 1-3

[0107] In a reaction vessel, 31 g of compound 1-2 (103.06 mmol) was dissolved in chlorobenzene, and 3.1 mL of Eaton's reagent was slowly added dropwise. After completion of the dropwise addition, the mixture was further stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was washed with distilled water, and an organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 24.4 g of compound 1-3 (yield: 88%).

4) Synthesis of Compound 1-4

[0108] 9.0 g of compound 1-3 (29.77 mmol), 9.1 g of bis(pinacolato)diboron (35.72 mmol), 1.1 g of tris(dibenzylideneacetone)dipalladium(0) (1.19 mmol), 1.0 g of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (s-phos) (2.38 mmol), 8.8 g of potassium acetate (89.31 mmol) and 150 mL of 1,4-dioxane were added to a reaction vessel, and the mixture was stirred under reflux at 130° C. for 6 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and an organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain 9.0 g of compound 1-4 (yield: 84%).

5) Synthesis of Compound C-584

[0109] 4.5 g of compound 1-4 (12.49 mmol), 6.6 g of 2-(3′-bromo-[1,1′-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (14.20 mmol), 0.4 g of tetrakis(triphenylphosphine)palladium(0) (0.34 mmol), 3.0 g of sodium carbonate (28.38 mmol), 55 mL of toluene, 14 mL of ethanol, and 14 mL of distilled water were added to a reaction vessel, and the mixture was stirred at 130° C. for 4 hours. After completion of the reaction, the precipitated solid was washed with distilled water and methanol. The residue was purified by column chromatography to obtain 3.9 g of compound C-584 (yield: 51%).

TABLE-US-00009 MW M.P. C-584 617.7 268° C.

[0110] Hereinafter, the properties of an OLED according to the present disclosure will be explained in detail. However, the following examples merely illustrate the properties of an OLED according to the present disclosure in detail, but the present disclosure is not limited to the following examples.

DEVICE EXAMPLES 1-1 TO 1-4: PRODUCING AN OLED DEPOSITED WITH A FIRST HOST COMPOUND AND A SECOND HOST COMPOUND ACCORDING TO THE PRESENT DISCLOSURE AS HOSTS

[0111] An OLED according to the present disclosure was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (10 Ω/sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone, trichloroethylene, acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and the pressure in the chamber of the apparatus was then controlled to 10.sup.−6 torr. Thereafter, an electric current was applied to the cell to evaporate the above-introduced material, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate. Next, compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer. Compound HT-1 was then introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer. Compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After forming the hole injection layers and the hole transport layers, a light-emitting layer was formed thereon as follows: The first host compound and the second host compound shown in Table 1 were introduced into two cells of the vacuum vapor depositing apparatus, respectively, as hosts and compound D-39 was introduced into another cell as a dopant. The two host materials were evaporated at a rate of 1:1, and at the same time the dopant material was evaporated at different rates to be deposited in a doping amount of 3 wt % based on the total amount of the hosts and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer. Next, compound ET-1 and compound EI-1 were evaporated at a rate of 1:1 in two other cells to deposit an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing compound EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an AI cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED was produced.

DEVICE EXAMPLES 2-1 AND 2-2: PRODUCING AN OLED DEPOSITED WITH A FIRST HOST COMPOUND AND A SECOND HOST COMPOUND ACCORDING TO THE PRESENT DISCLOSURE AS HOSTS

[0112] An OLED was produced in the same manner as in Device Example 1-1, except that the second hole transport layer was deposited to a thickness of 45 nm using compound HT-3, and compound EB-1 was deposited to a thickness of 15 nm as an electron blocking layer thereon, and the first host compound and the second host compound shown in Table 1 below were used.

COMPARATIVE EXAMPLES 1-1 TO 1-4: PRODUCING AN OLED COMPRISING COMPARATIVE COMPOUND AS A HOST(S)

[0113] An OLED was produced in the same manner as in Device Example 1-1, except that only the second host compound shown in Table 1 below was used in Comparative Examples 1-1 and 1-2, and the first host compound and the second host compound shown in Table 1 were used in Comparative Examples 1-3 and 1-4.

[0114] The power efficiency at a luminance of 1,000 nit, and the time taken for luminance to decrease from 100% to 95% (lifetime; T95) at a luminance of 5,000 nit of the OLEDs produced in the Device Examples and the Comparative Examples are provided in Table 1 below.

TABLE-US-00010 TABLE 1 Power Lifetime Second Efficiency T95 First Host Host [Im/W] [hr] Device Example 1-1 H-1-61 C-5  31.2 387 Device Example 1-2 H-1-61 C-146 30.6 261 Device Example 1-3 H-1-91 C-489 28.9 136 Device Example 1-4 H-1-58 C-489 32.3 169 Device Example 2-1 H-1-57 C-491 32.1 100 Device Example 2-2 H-1-39 C-13  32.0 285 Comparative — C-146 28.7 11 Example 1-1 Comparative — C-491 25.9 19 Example 1-2 Comparative A-1 C-146 29.4 76 Example 1-3 Comparative A-2 C-146 29.5 14 Example 1-4

[0115] From Table 1, it can be confirmed that the OLEDs comprising a specific combination of compounds according to the present disclosure as a host material exhibit an equivalent or improved level of power efficiency and significantly improved lifetime compared to the conventional OLEDs.

[0116] DEVICE EXAMPLES 3 TO 7: PRODUCING A RED OLED DEPOSITED WITH A FIRST HOST COMPOUND AND A SECOND HOST COMPOUND ACCORDING TO THE PRESENT DISCLOSURE AS HOSTS

[0117] An OLED according to the present disclosure was produced as follows: An OLED according to the present disclosure was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (10 Ω/sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone and isopropyl alcohol, sequentially, and then was stored in isopropyl alcohol. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-3 was introduced into a cell of the vacuum vapor deposition apparatus, and compound HT-1 was introduced into another cell of the vacuum vapor deposition apparatus. The two materials were evaporated at different rates and compound HI-3 was deposited in a doping amount of 3 wt % based on the total amount of compound HI-3 and compound HT-1 to form a hole injection layer having a thickness of 10 nm on the ITO substrate. Next, compound HT-1 was deposited on the first hole injection layer to form a first hole transport layer having a thickness of 80 nm. Subsequently, compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layers, a light-emitting layer was formed thereon as follows: The first and second host compounds shown in Table 2 below were introduced into two cells of the vacuum vapor depositing apparatus as hosts, and compound D-39 was introduced into another cell. The two host materials were evaporated at a rate of 1:1 and the dopant material was simultaneously evaporated at a different rate and the dopant was deposited in a doping amount of 3 wt % based on the total amount of the hosts and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer. Next, compound ET-1 and compound EI-1 as electron transport materials were evaporated at a weight ratio of 50:50 to deposit an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing compound EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an AI cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED was produced. Each compound was used after purification by vacuum sublimation under 10.sup.−6 torr for each material.

COMPARATIVE EXAMPLES 2 AND 3: PRODUCING AN OLED COMPRISING COMPARATIVE COMPOUND AS A HOST

[0118] An OLED was produced in the same manner as in Device Example 3, except that only the second host compound shown in Table 2 below was used as a host material.

[0119] The driving voltage, the luminous efficiency, and the emission color at a luminance of 1,000 nit, and the time taken for luminance to decrease from 100% to 95% (lifetime; T95) at a luminance of 5,000 nit of the OLEDs produced in Device Examples 3 to 7 and Comparative Examples 2 and 3 are provided in Table 2 below.

TABLE-US-00011 TABLE 2 Life- Driving Luminous time First Second Voltage Efficiency Emission T95 Host Host [V] [cd/A] Color [hr] Device H-1- C-254 3.1 35.8 Red 356 Example 3 91 Device H-1- C-254 3.2 32.6 Red 113 Example 4 58 Device H-1- C-263 3.1 34.5 Red 393 Example 5 91 Device H-1- C-263 3.0 34.5 Red 346 Example 6 58 Device H-1- C-588 2.9 32.1 Red 385 Example 7 39 Comparative — C-263 3.5 27.9 Red 38.2 Example 2 Comparative — C-588 3.4 23.9 Red 19.5 Example 3

[0120] From Table 2, it can be confirmed that the OLED comprising a specific combination of compounds according to the present disclosure as a plurality of host materials have significantly improved driving voltage, luminous efficiency and/or lifetime properties compared to the conventional OLEDs.

[0121] The compounds used in the Device Examples and the Comparative Examples are shown in Table 3 below.

TABLE-US-00012 TABLE 3 Hole Injection Layer/Hole Transport Layer [00237] [00238] [00239] [00240] [00241] [00242] [00243] Light-Emitting Layer [00244] [00245] [00246] [00247] [00248] [00249] [00250] [00251] [00252] [00253] [00254] [00255] [00256] [00257] [00258] [00259] Electron Transport Layer/Electron Injection Layer [00260] [00261]