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 comprising a compound represented by formula 1, and a second host material comprising 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 higher luminous efficiency and/or longer lifetime properties as compared with a conventional organic electroluminescent device.

Claims

1. A plurality of host materials comprising a first host material comprising a compound represented by the following formula 1, and a second host material comprising a compound represented by the following formula 3: ##STR00107## wherein, ring A, ring B, and ring C, each independently, represent a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring; Y represents O, S, or NRa; Ra represents —L.sub.2—Ar.sub.2; Ar.sub.1 and Ar.sub.2, each independently, represent a substituted or unsubstituted (C6-C30)aryl; a substituted or unsubstituted (3- to 30-membered)heteroaryl containing at least one of nitrogen(s), oxygen(s), and sulfur(s); or a substituted or unsubstituted di(C6-C30)arylamino; L.sub.1 and L.sub.2, each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; and n represents an integer of 0 or 1, with the proviso that if n is 0, both ring A and ring B are a substituted or unsubstituted naphthalene ring; ##STR00108## wherein, Ar.sub.1 and Ar.sub.22, each independently, represent a phenyl unsubstituted or substituted with deuterium(s), a biphenyl unsubstituted or substituted with deuterium(s), a terphenyl unsubstituted or substituted with deuterium(s), or a naphthyl unsubstituted or substituted with deuterium(s); L.sub.21 represents a naphthylene unsubstituted or substituted with deuterium(s), or a biphenylene unsubstituted or substituted with deuterium(s); R.sub.1, R.sub.4, R.sub.5, and R.sub.8, each independently, represent hydrogen, deuterium, a phenyl unsubstituted or substituted with deuterium(s), a biphenyl unsubstituted or substituted with deuterium(s), a terphenyl unsubstituted or substituted with deuterium(s), or a naphthyl unsubstituted or substituted with deuterium(s); and R.sub.2, R.sub.3, R.sub.6, and R.sub.7, each independently, represent hydrogen or deuterium; with the proviso that if both Ar.sub.21 and Ar.sub.22 represent phenyl, at least one of R.sub.1, R.sub.4, R.sub.5, and R.sub.8 is not hydrogen or deuterium.

2. The plurality of host materials according to claim 1, wherein the substituents of the substituted benzene, the substituted naphthalene, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, and diarylamino, 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 50-membered)heteroaryl unsubstituted or substituted with at least one of a (C1-C30)alkyl(s), a (C6-C30)aryl(s), and a di(C6-C30)arylamino(s); a (C6-C30)aryl unsubstituted or substituted with at least one of deuterium(s), a cyano(s), a (C1-C30)alkyl(s), a (3- to 50-membered)heteroaryl(s), a di(C6-C30)arylamino(s), and a tri(C6-C30)arylsilyl(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 any one of the following formulas 1-1 to 1-7: ##STR00109## ##STR00110## wherein, Ar.sub.1, L.sub.1, and Y are as defined in claim 1; R.sub.11 to R.sub.27, 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; and a, d, h, m, q, and r, each independently, represent an integer of 1 to 6; and b, c, e, f, g, i, j, k, I, o, and p, each independently, represent an integer of 1 to 4, in which if a to m and o to r, each independently, are an integer of 2 or more, each of R.sub.11, each of R.sub.12, each of R.sub.13, each of R.sub.14, each of R.sub.15, each of R.sub.16, each of R.sub.17, each of R.sub.18, each of R.sub.19, each of R.sub.20, each of R.sub.21, each of R.sub.22, each of R.sub.23, each of R.sub.24, each of R.sub.25, each of R.sub.26, and each of R.sub.27 may be the same or different.

4. The plurality of host materials according to claim 1, wherein Ar.sub.1 represents a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted benzofuropyrimidinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzoquinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted benzocarbazolyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzothiophenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted benzonaphthofuranyl, a substituted or unsubstituted benzonaphthothiophenyl, a substituted or unsubstituted diphenylamino, a substituted or unsubstituted naphthylphenylamino, or a substituted or unsubstituted biphenylphenylamino.

5. The plurality of host materials according to claim 1, wherein the compound represented by formula 1 is at least one selected from the following compounds: ##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118## ##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127## ##STR00128## ##STR00129## ##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134## ##STR00135##

6. The plurality of host materials according to claim 1, wherein the compound represented by formul 3 is at least one selected from the following compounds: ##STR00136## ##STR00137## ##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147##

7. An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein the 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 H1-131

(1) ##STR00074##

(2) Synthesis of Compound 1

(3) 7H-dibenzo[c,g]carbazole (60 g, 224 mmol) was dissolved in 900 mL of N,N-dimethylformamide (DMF) in a flask, and the mixture was cooled to 0° C. and stirred. N-bromosuccinimide (NBS) (36 g, 202 mmol) was dissolved in 220 mL of DMF, and was then added dropwise to the mixture for 2.5 hours. The resulting mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction product was washed with an aqueous Na.sub.2S.sub.2O.sub.3 solution and water, an organic layer was extracted with ethyl acetate, and the residual moisture was removed with MgSO.sub.4. The residue was dried and separated by a silica filter to obtain compound 1 (79 g, yield: 79%).

(4) Synthesis of Compound 2

(5) Compound 1 (76 g, 220 mmol), iodobenzene (90 g, 439 mmol), CuI (20.90 g, 110 mmol), ethylenediamine (EDA) (13 g, 110 mmol), and K.sub.3PO.sub.4 (139 g, 659 mmol) were added to 1.1 L of toluene, and the mixture was stirred under reflux for 2.5 hours. MeOH was added to the mixture, and the resulting solid was filtered under reduced pressure. The residue was separated by column chromatography to obtain compound 2 (55.1 g, yield: 60%).

(6) Synthesis of Compound 3

(7) Compound 2 (54.6 g, 129 mmol), 2-chloroaniline (20 g, 155 mmol), Pd(OAc).sub.2 (2.9 g, 13 mmol), P(t-Bu).sub.3 (5.2 g, 26 mmol), sodium tert-butoxide (NaOt-Bu) (31 g, 323 mmol), and 650 mL of toluene were stirred under reflux for 4 hours. The mixture was cooled to room temperature and NH.sub.4Cl (aq) was added thereto. The reaction product was extracted with ethyl acetate (EA) and dried with magnesium sulfate. The residue was distilled under reduced pressure, and separated by column chromatography to obtain compound 3 (47.9 g, yield: 79%).

(8) Synthesis of Compound 4

(9) Compound 3 (48 g, 103 mmol), Pd(OAc).sub.2 (2.3 g, 10 mmol), ligand (tricyclohexylphosphonium tetrafluoroborate) (7.6 g, 21 mmol), Cs.sub.2CO.sub.3 (100 g, 308 mmol), and 400 mL of N,N-dimethylacetamide (DMA) were stirred under reflux for 1 hour. The reaction product was cooled to room temperature and NH.sub.4Cl (aq) was added thereto. An organic layer was extracted with methylene chloride (MC) and dried with magnesium sulfate. The residue was distilled under reduced pressure, and separated by column chromatography to obtain compound 4 (44 g, yield: 79%).

(10) Synthesis of Compound H1-131

(11) Compound 4 (5 g, 12 mmol), iodobenzene (3.5 g, 17 mmol), CuI (1.1 g, 6 mmol), 1,2-diaminocyclohexane (2.6 g, 23 mmol), and K.sub.3PO.sub.4 (4.9 g, 23 mmol) were added to 60 mL of o-xylene, and the mixture was stirred under reflux for one day. The reaction product was cooled to room temperature and was subjected to celite filter using MC. The filtrate was distilled under reduced pressure, and separated by column chromatography using MC/Hex to obtain compound H1-131 (1.3 g, yield: 22%).

(12) .sup.1H NMR (600 MHz, DMSO, δ) 9.16-9.15 (d, 1H), 8.99-8.98 (d, 1H), 8.14-8.13 (d, 1H), 7.94-7.93 (d, 1H), 7.94-7.68 (m, 9H), 7.65-7.61 (m, 3H), 7.60-7.54 (m, 3H), 7.25-7.21 (m, 2H), 7.08-7.07 (d, 1H), 6.78-6.76 (m, 1H) 5.95-5.94 (d, 1H)

(13) TABLE-US-00001 MW UV PL M.P. H1-131 508.62 342 nm 427 nm 184° C.

EXAMPLE 2: PREPARATION OF COMPOUND H1-132

(14) ##STR00075##

(15) Compound 4 (7 g, 16 mmol), 2-bromonaphthalene (6.7 g, 32 mmol), CuI (1.5 g, 8 mmol), 1,2-diaminocyclohexane (3.7 g, 32 mmol), and K.sub.3PO.sub.4 (10.3 g, 49 mmol) were added to 80 mL of o-xylene, and the mixture was stirred under reflux for one day. The reaction product was cooled to room temperature and was subjected to celite filter using MC. The filtrate was distilled under reduced pressure, and separated by column chromatography using MC/Hex to obtain compound H1-132 (1.3 g, yield: 22%).

(16) .sup.1H NMR (600 MHz, DMSO, δ) 9.17-9.15 (d, 1H), 9.00-8.99 (d, 1H), 8.31-8.30 (m, 2H), 8.20-8.18 (d, 1H), 8.15-8.14 (d, 1H), 8.11-8.10 (d, 1H), 7.95-7.94 (d, 1H), 7.83-7.79 (m, 5H), 7.73-7.69 (m, 4H), 7.60-7.57 (m, 4H), 7.21-7.18 (m, 2H), 7.14-7.13 (d, 1H), 6.78-6.77 (t, 1H) 5.98-5.96 (d, 1H)

(17) TABLE-US-00002 MW UV PL M.P. H1-132 558.68 340 nm 431 nm 263° C.

EXAMPLE 3: PREPARATION OF COMPOUND H1-134

(18) ##STR00076## ##STR00077##

(19) Synthesis of Compound 5

(20) Compound 1 (15 g, 220 mmol), 3-iodo-1,1′-biphenyl (18 g, 65 mmol), CuI (4.1 g, 22 mmol), ethylenediamine (2.6 g, 43 mmol), and K.sub.3PO.sub.4 (23 g, 108 mmol) were added to 216 mL of toluene, and the mixture was stirred under reflux for 4 hours. MeOH was added to the mixture, and the resulting solid was filtered under reduced pressure. The filtrate was separated by column chromatography to obtain compound 5 (16 g, yield: 74%).

(21) Synthesis of Compound 6

(22) Compound 5 (15 g, 30 mmol), 2-chloroaniline (7.7 g, 60 mmol), Pd(OAc).sub.2 (0.67 g, 3 mmol), P(t-Bu).sub.3 (1.2 g, 6 mmol), NaOt-Bu (7.2 g, 75 mmol), and 150 mL of toluene were stirred under reflux for 2 hours. The reaction product was cooled to room temperature and NH.sub.4Cl (aq) was added thereto. An organic layer was extracted with EA and dried with magnesium sulfate. The residue was distilled under reduced pressure, and separated by column chromatography to obtain compound 6 (10.1 g, yield: 62%).

(23) Synthesis of Compound 7

(24) Compound 6 (10 g, 18 mmol), Pd(OAc).sub.2 (0.41 g, 1.8 mmol), ligand (tricyclohexylphosphonium tetrafluoroborate) (1.35 g, 3.7 mmol), Cs.sub.2CO.sub.3 (18 g, 55 mmol), and 92 mL of DMA were stirred under reflux for 1 hour. The reaction product was cooled to room temperature and NH.sub.4Cl (aq) was added thereto. An organic layer was extracted with MC and dried with magnesium sulfate. The residue was distilled under reduced pressure, and separated by column chromatography to obtain compound 7 (7.1 g, yield: 76%).

(25) Synthesis of Compound H1-134

(26) Compound 7 (6.7 g, 13 mmol), 3-iodo-1,1-biphenyl (7.4 g, 26 mmol), Cu powder (0.42 g, 7 mmol), and K.sub.2CO.sub.3 (3.6 g, 26 mmol) were added to 70 mL of o-dichlorobenzene, and the mixture was stirred under reflux for one day. The reaction product was cooled to room temperature and was subjected to celite filter using MC. The filtrate was distilled under reduced pressure, and separated by column chromatography using MC/Hex to obtain compound M1-134 (3.1 g, yield: 36%).

(27) .sup.1H NMR (600 MHz, DMSO, δ) 9.18-9.17 (d, 1H), 9.01-9.00 (d, 1H), 8.16-8.15 (d, 1H), 8.11-8.09 (d, 1H), 8.06-8.05 (m, 2H), 8.00-7.79 (m, 7H), 7.73-7.57 (m, 8H), 7.48-7.38 (m, 6H), 7.30-7.28 (t, 1H), 7.22-7.18 (m, 2H), 6.80-6.78 (t, 1H), 6.07-6.06 (d, 1H)

(28) TABLE-US-00003 MW M.P. H1-134 660.82 259° C.

EXAMPLE 4: PREPARATION OF COMPOUND H1-133

(29) ##STR00078##

(30) Compound 4 (4 g, 9.25 mmol), 3-iodo-1,1′-biphenyl (3.1 g, 11.1 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd.sub.2(dba).sub.3) (0.42 g, 0.46 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos) (0.38 g, 0.92 mmol), and NaOt-Bu (2.2 g, 23.13 mmol) were added to 46 mL of o-xylene, and the mixture was stirred under reflux for one day. The reaction product was extracted with MC, distilled under reduced pressure, and separated by column chromatography using MC/Hex to obtain compound 133 (1.2 g, yield: 23%).

(31) .sup.1H NMR (600 MHz, DMSO, δ) 9.17-9.15 (d, 1H), 9.00-8.98 (d, 1H), 8.15-8.13 (d, 1H), 8.07-8.06 (d, 1H), 7.98 (m, 1H), 7.95-7.94 (d, 1H), 7.88-7.86 (t, 1H), 7.82-7.80 (m, 7H), 7.71-7.67 (m, 2H), 7.65-7.61 (m, 2H), 7.60-7.55 (m, 2H), 7.49-7.47 (t, 2H), 7.42-7.39 (t, 1H), 7.30-7.27 (t, 1H), 7.26-7.23 (t, 1H), 7.20-7.19 (d, 1H), 6.80-6.77 (t, 1H), 5.97-5.95 (d, 1H)

(32) TABLE-US-00004 MW M.P. H1-133 584.7 249.6° C.

EXAMPLE 5: PREPARATION OF COMPOUND H1-135

(33) ##STR00079## ##STR00080##

(34) Synthesis of Compound 1

(35) 7H-dibenzo[c,g]carbazole (50 g, 187 mmol) was dissolved in 750 mL of DMF in a flask, and the mixture was cooled to 0° C. and stirred. NBS (30 g, 168 mmol) was dissolved in 250 mL of DMF, and was then added dropwise to the mixture for 1 hour. The resulting mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction product was washed with an aqueous Na.sub.2S.sub.2O.sub.3 solution and water, an organic layer was extracted with ethyl acetate, and the residual moisture was removed with MgSO.sub.4. The residue was dried and separated by a silica filter to obtain compound 1 (40 g, yield: 62%).

(36) Synthesis of Compound 8

(37) Compound 1 (11 g, 32 mmol), 4-iodo-1,1′-biphenyl (17.8 g, 64 mmol), CuI (3.0 g, 15.9 mmol), ethylenediamine (1.91 g, 31.8 mmol), and K.sub.3PO.sub.4 (20.3 g, 95 mmol) were added to 160 mL of toluene, and the mixture was stirred under reflux for 4 hours. MeOH was added to the mixture, and the resulting solid was filtered under reduced pressure. The filtrate was separated by column chromatography to obtain compound 8 (13.0 g, yield: 82%).

(38) Synthesis of Compound 9

(39) Compound 8 (13.0 g, 26 mmol), 2-chloroaniline (6.7 g, 52 mmol), Pd(OAc).sub.2 (0.59 g, 2.6 mmol), P(t-Bu).sub.3 (1.1 g, 5.2 mmol), NaOt-Bu (6.3 g, 65 mmol), and 130 mL of toluene were stirred under reflux for 4 hours. The reaction product was cooled to room temperature and NH.sub.4Cl(aq) was added thereto. An organic layer was extracted with EA and dried with magnesium sulfate. The residue was distilled under reduced pressure, and separated by column chromatography to obtain compound 9 (9.2 g, yield: 65%).

(40) Synthesis of Compound 10

(41) Compound 9 (9.2 g, 17 mmol), Pd(OAc).sub.2 (0.38 g, 2 mmol), ligand (tricyclohexylphosphonium tetrafluoroborate) (1.2 g, 3 mmol), Cs.sub.2CO.sub.3 (138 g, 42 mmol), and 70 mL of DMA were stirred under reflux for 1 hour. The reaction product was cooled to room temperature and NH.sub.4Cl(aq) was added thereto. The resulting solid was distilled under reduced pressure, and separated by column chromatography to obtain compound 10 (6.0 g, yield: 70%).

(42) Synthesis of Compound H1-135

(43) Compound 10 (6 g, 12 mmol), 2-bromonaphthalene (4.9 g, 24 mmol), CuI (1.1 g, 6 mmol), 1,2-diaminocyclohexane (2.7 g, 24 mmol), and K.sub.3PO.sub.4 (7.5 g, 35 mmol) were added to 60 mL of o-xylene, and the mixture was stirred under reflux for one day. The reaction product was cooled to room temperature. Then, an organic layer was separated by adding ethyl acetate and water, and dried with magnesium sulfate. The residue was subjected to celite filter using MC. The filtrate was distilled under reduced pressure, and separated by column chromatography using MC/Hex to obtain compound H1-135 (2.1 g, yield: 28%).

(44) .sup.1H NMR (600 MHz, DMSO, δ) 9.18-9.17 (d, 1H), 9.01-8.99 (d, 1H), 8.33-8.31 (m, 2H), 8.20-8.19 (d, 1H), 8.17-8.15 (d, 1H), 8.12-8.08 (m, 3H), 7.98-7.97 (d, 1H), 7.93-7.89 (m, 4H), 7.70-7.68 (m, 5H), 7.63-7.57 (m, 5H) 7.50-7.48 (t, 1H), 7.22-7.19 (t, 1H), 7.15-7.13 (d, 1H), 6.77-6.74 (td, 1H), 6.16-6.15 (d, 1H)

(45) TABLE-US-00005 MW M.P. H1-135 508.62 294° C.

(46) Example 6: Preparation of compound H1-11

(47) ##STR00081##

(48) Compound 1-1 (7 g, 13 mmol), dibenzo[b,d]furan-1-ylboronic acid (3 g, 14.3 mmol), K.sub.2CO.sub.3 (5.4 g, 39 mmol), and Pd(PPh.sub.3).sub.4 (0.75 g, 0.65 mmol) were dissolved in 30 mL of H.sub.2O, 60 mL of toluene, and 30 mL of EtOH in a flask, and the mixture was refluxed at 120° C. for 3 hours. After completion of the reaction, an organic layer was extracted with ethyl acetate, and the residual moisture was removed with magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound H1-11 (5.7 g, yield: 70%).

(49) .sup.1H NMR (600 MHz, CDCl.sub.3, δ) 9.305 (s, 1H), 9.049-9.035 (d, J=8.4 Hz, 1H), 8.379-8.367 (d, J=7.2 Hz, 1H), 8.022-8.008 (d, J=8.4 Hz, 1H) 7.816-7.705 (m, 6H), 7.699-7.392 (m, 16H) 7.195-7.127 (m, 2H)

(50) TABLE-US-00006 MW M.P. H1-11 642.73 154° C.

EXAMPLE 7: PREPARATION OF COMPOUND H1-54

(51) ##STR00082##

(52) Compound 1-2 (5.7 g, 10.6 mmol), dibenzo[b,d]furan-1-ylboronic acid (2.5 g, 11.7 mmol), K.sub.2CO.sub.3 (4.4 g, 31.8 mmol), and Pd(PPh.sub.3).sub.4 (0.61 g, 0.653 mmol) were dissolved in 30 mL of H.sub.2O, 60 mL of toluene, and 30 mL of EtOH in a flask, and the mixture was refluxed at 120° C. for 3 hours. After completion of the reaction, an organic layer was extracted with ethyl acetate, and the residual moisture was removed with magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound H1-54 (1.2 g, yield: 18%).

(53) .sup.1H NMR (600 MHz, CDCl.sub.3, δ) 8.880 (s, 1H), 8.378-8.364 (d, J=8.4 Hz, 1H), 8.297-8.284 (d, J=7.8 Hz, 1H), 8.000-7.987 (d, J=7.8 Hz, 1H) 7.777-7.702 (m, 5H), 7.615-7.332 (m, 15H), 7.189-7.127 (m, 4H)

(54) TABLE-US-00007 MW M.P. H1-54 624.73 239° C.

EXAMPLE 8: PREPARATION OF COMPOUND H1-53

(55) ##STR00083##

(56) Compound 1-2 (5.0 g, 9.3 mmol), dibenzo[b,d]furan-4-ylboronic acid (2.2 g, 10.2 mmol), Pd(PPh.sub.3).sub.4 (0.54 g, 0.47 mmol), and K.sub.2CO.sub.3, (2.6 g, 18.6 mmol) were dissolved in 20 mL of toluene, 8 mL of EtOH, and 10 mL of H.sub.2O in a flask, and the mixture was refluxed at 120° C. for 3 hours. After completion of the reaction, an organic layer was extracted with ethyl acetate, and the residual moisture was removed with magnesium sulfate. The residue was dried and separated by column chromatography to obtain compound H1-53 (3.5 g, yield: 60%).

(57) .sup.1H NMR (600 MHz, DMSO.sub.3, δ) 9.210 (s, 1H), 8.516-8.502 (d, 1H), 8.408-8.395 (d, 1H), 8.219-8.198 (m, 2H), 8.115-8.109 (t, 1H), 8.087-8.073 (d, 1H), 8.040-8.028 (d, 1H), 7.856-7.842 (d, 1H), 7.833-7.807 (t, 1H), 7.733-7.611 (m, 9H), 7.562-7.531 (m, 2H), 7.515-7.490 (t, 1H), 7.451-7.426 (t, 1H), 7.293-7.279 (d, 1H), 7.258-7.232 (t, 1H), 7.119 (s, 1H)

(58) TABLE-US-00008 MW M.P. H1-53 624.7 161° C.

EXAMPLE 9: PREPARATION OF COMPOUND H1-13

(59) ##STR00084##

(60) 7-phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (3.6 g, 9.285 mmol), 1-(4-bromophenyl)dibenzo[b,d]furan (3 g, 9.285 mmol), CuI (0.08 g, 0.464 mmol), EDA (0.5 g, 9.285 mmol), and K.sub.3PO.sub.4 (4.9 g, 23.21 mmol) were added to 50 mL of xylene, and the mixture was stirred for one day. After completion of the reaction, the reaction product was cooled to room temperature, and extracted with distilled water and MeOH. The extracted product was separated by column chromatography using MC/Hex to obtain compound H1-13 (2.7 g, yield: 47%).

(61) .sup.1H NMR (DMSO-d.sub.6) δ: 9.69 (s, 1H), 9.26 (d, J=8.3 Hz, 1H), 8.69 (dd, J=7.7, 1.2 Hz, 1H), 8.14 (dd, J=8.0, 1.1 Hz, 1H), 7.97 (d, J=8.8 Hz, 1H), 7.92 (s, 4H), 7.88 (ddd, J=8.2, 6.9, 1.3 Hz, 1H), 7.82-7.76 (m, 4H), 7.73 (t, J=7.8 Hz, 2H), 7.70-7.48 (m, 8H), 7.48-7.44 (m, 2H), 7.42 (td, J=7.3, 1.0 Hz, 1H), 7.26-7.20 (m, 1H)

(62) TABLE-US-00009 MW M.P. H1-13 624.7 309.7° C.

EXAMPLE 10: PREPARATION OF COMPOUND H1-5

(63) ##STR00085##

(64) 7-phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (7.6 g, 18.88 mmol), 3-chloro-1,1′:2′,1″-terphenyl (5 g, 18.88 mmol), Pd.sub.2(dba).sub.3 (0.86 g, 0.940 mmol), NaOt-Bu (4.5 g, 47.22 mmol), and P(t-Bu).sub.3 (0.38 g, 1.888 mmol) were added to 100 mL of toluene, and the mixture was stirred for one day. After completion of the reaction, the reaction product was cooled to room temperature, and extracted with distilled water and MeOH. The extracted product was separated by column chromatography using MC/Hex to obtain compound H1-5 (0.7 g, yield: 6.2%).

(65) .sup.1H NMR (DMSO-d.sub.6) δ: 9.58 (s, 1H), 9.20 (d, J=8.4 Hz, 1H), 8.57 (d, J=7.8 Hz, 1H), 8.11 (d, J=8.3 Hz, 1H), 7.94 (d, J=8.9 Hz, 1H), 7.84 (ddd, J=8.3, 6.8, 1.3 Hz, 1H), 7.72 (d, J=6.2 Hz, 4H), 7.64-7.47 (m, 8H), 7.44 (dt, J=6.0, 1.9 Hz, 1H), 7.40-7.17 (m, 10H), 6.50 (d, J=7.9 Hz, 1H)

(66) TABLE-US-00010 MW M.P. H1-5 610.7 194.6° C.

EXAMPLE 11: PREPARATION OF COMPOUND H1-19

(67) ##STR00086##

(68) 7-phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (5.1 g, 13 mmol), 9-(3-bromophenyl)-9H-carbazole (4.7 g, 14.6 mmol), Pd.sub.2(dba).sub.3 (0.604 g, 0.66 mmol), SPhos (0.546 g, 1.33 mmol), and NaOt-Bu (3.20 g, 33.3 mmol) were added to 50 mL of xylene in a flask, and the mixture was stirred under reflux at 190° C. for 2 hours. After completion of the reaction, an organic layer was extracted with EA, dried with MgSO.sub.4, and separated by column chromatography. Then, MeOH was added to the separated product, and the resulting solid was filtered under reduced pressure to obtain compound H1-19 (4.4 g, yield: 53.0%).

(69) .sup.1H NMR (600 MHz, DMSO-d.sub.6, δ) 9.66 (s, 1H), 9.24 (d, J=8.4 Hz, 1H), 8.66 (d, J=7.7 Hz, 1H), 8.26 (d, J=7.8 Hz, 2H), 8.13 (d, J=8.1 Hz, 1H), 8.01-7.94 (m, 2H), 7.91-7.84 (m, 3H), 7.79 (dd, J=8.2, 1.8 Hz, 1H), 7.77-7.74 (m, 2H), 7.69 (t, J=7.6 Hz, 2H), 7.62-7.55 (m, 3H), 7.53 (d, J=8.1 Hz, 1H), 7.49-7.45 (m, 2H), 7.39 (dd, J=14.4, 6.9 Hz, 5H) 7.31 (t, J=7.5 Hz, 2H)

(70) TABLE-US-00011 MW M.P. H1-19 623/6 240° C.

EXAMPLE 12: PREPARATION OF COMPOUND H1-6

(71) ##STR00087##

(72) 7-phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (5.0 g, 13 mmol), 4′-bromo-1,1′:3′,1″-terphenyl (6.06 g, 20 mmol), Cu powder (1.307 g, 0.65 mmol), and K.sub.2CO.sub.3 (3.4 g, 26 mmol) were added to 60 mL of o-dichlorobenzene (o-DCB) in a flask, and the mixture was stirred under reflux at 230° C. for 12 hours. After completion of the reaction, an organic layer was extracted with EA, dried with MgSO.sub.4, and separated by column chromatography. Then, MeOH was added to the separated product, and the resulting solid was filtered under reduced pressure to obtain compound H1-6 (1.3 g, yield: 16.3%).

(73) .sup.1H NMR (600 MHz, DMSO-d.sub.6, δ) 9.51 (s, 1H), 9.16 (d, J=8.3 Hz, 1H), 8.57 (d, J=7.8 Hz, 1H), 8.10 (d, J=8.0 Hz, 1H), 7.98-7.85 (m, 6H), 7.83 (t, J=7.6 Hz, 1H), 7.76 (s, 1H), 7.70 (d, J=8.1 Hz, 1H), 7.61-7.51 (m, 5H), 7.51-7.42 (m, 3H), 7.38 (t, J=7.8 Hz, 1H), 7.31 (t, J=7.3 Hz, 1H), 7.25 (d, J=8.0 Hz, 1H), 7.13-7.06 (m, 4H), 7.03 (d, J=6.8 Hz, 1H), 6.79 (s, 1H)

(74) TABLE-US-00012 MW M.P. H1-6 610.74 296° C.

EXAMPLE 13: PREPARATION OF COMPOUND H1-22

(75) ##STR00088##

(76) Synthesis of Compound 11

(77) 7-phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (10 g, 26.14 mmol), 1-bromo-3-iodobenzene (14.8 g, 52.29 mmol), CuI (2.5 g, 13.07 mmol), EDA (1.57 g, 26.14 mmol), and K.sub.3PO.sub.4 (13.8 g, 65.36 mmol) were added to 130 mL of toluene, and the mixture was stirred for one day. After completion of the reaction, the reaction product was cooled to room temperature, and extracted with distilled water and MeOH. The extracted product was separated by column chromatography using MC/Hex to obtain compound 11 (9 g, yield: 64%).

(78) Synthesis of Compound 12

(79) Compound 11 (9 g, 16.74 mmol) was added to 85 mL of THF, and n-BuLi (2.5 M) (8.7 mL, 21.77 mmol) was then slowly added thereto while stirring at −78° C. for 1 hour. B(Oi-pr).sub.3 (5.7 mL, 25.12 mmol) was added to the mixture, and then stirred for one day. After completion of the reaction, NH.sub.4Cl and distilled water were added to the reaction product, and the mixture was stirred for 30 minutes. Next, the resulting product was extracted with distilled water and EA, and an organic layer was concentrated to obtain compound 12 (6.8 g, yield: 80%).

(80) Synthesis of Compound H1-22

(81) Compound 12 (6.8 g, 13.53 mmol), 4-bromo-9,9-dimethyl-9H-fluorene (3.7 g, 13.53 mmol), Pd(PPh.sub.3).sub.4 (0.8 g, 0.676 mmol), and K.sub.2CO.sub.3 (3.7 g, 27.07 mmol) were added to 60 mL of toluene, 15 mL of EtOH, and 15 mL of distilled water, and the mixture was stirred under reflux for 3 hours. After completion of the reaction, the reaction product was cooled to room temperature, and extracted with distilled water and EA. An organic layer was distilled under reduced pressure, and separated by column chromatography using MC/Hex to obtain compound H1-22 (1.5 g, yield: 17%).

(82) .sup.1H NMR (DMSO-d.sub.6) δ: 9.64 (s, 1H), 9.22 (d, J=8.4 Hz, 1H), 8.64 (dt, J=7.6, 0.9 Hz, 1H), 8.14-8.10 (m, 1H), 7.94 (d, J=8.9 Hz, 1H), 7.90-7.77 (m, 3H), 7.68 (s, 3H), 7.65-7.53 (m, 7H), 7.53-7.33 (m, 6H), 7.27 (td, J=7.4, 1.1 Hz, 1H), 7.17 (d, J=7.6 Hz, 1H), 6.92 (d, J=47.9 Hz, 2H), 1.49 (d, J=17.3 Hz, 6H)

(83) TABLE-US-00013 MW M.P. H1-22 650.8 166.3° C.

EXAMPLE 14: PREPARATION OF COMPOUND H1-4

(84) ##STR00089##

(85) 7-phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (5 g, 13.07 mmol), 4-bromo-1,1:2′,1″-terphenyl (4 g, 13.07 mmol), Pd.sub.2(dba).sub.3 (0.6 g, 0.653 mmol), NaOt-Bu (3.8 g, 39.21 mmol), and SPhos (0.5 g, 1.307 mmol) were added to 70 mL of o-xylene, and the mixture was stirred for one day. After completion of the reaction, the reaction product was cooled to room temperature, and extracted with distilled water and MeOH. The extracted product was separated by column chromatography using MC/Hex to obtain compound H1-4 (6.3 g, yield: 78%).

(86) NMR (DMSO-d.sub.6) δ: 9.63 (s, 1H), 9.23 (d, J=8.3 Hz, 1H), 8.63 (dd, J=7.7, 1.1 Hz, 1H), 8.12 (d, J=8.2 Hz, 1H), 7.95 (d, J=8.9 Hz, 1H), 7.85 (ddd, J=8.2, 6.8, 1.4 Hz, 1H), 7.79-7.73 (m, 2H), 7.72-7.66 (m, 3H), 7.60-7.47 (m, 8H), 7.44 (ddd, J=8.2, 7.1, 1.3 Hz, 1H), 7.38-7.33 (m, 3H), 7.32-7.24 (m, 2H), 7.22-7.14 (m, 5H)

(87) TABLE-US-00014 MW M.P. H1-4 610.7 288° C.

EXAMPLE 15: PREPARATION OF COMPOUND H1-12

(88) ##STR00090##

(89) Synthesis of Compound 13

(90) Dibenzo[b,d]thiophene-1-ylboronic acid (20 g, 87.71 mmol), 1-bromo-3-iodobenzene (50 g, 175.4 mmol), Pd(PPh.sub.3).sub.4 (5 g, 4.385 mmol), and Na.sub.2CO.sub.3 (18 g, 175.4 mmol) were added to 360 mL of toluene, 90 mL of distilled water, and 90 mL of EtOH, and the mixture was stirred under reflux for 3 hours. After completion of the reaction, the reaction product was cooled to room temperature, and extracted with distilled water and EA. An organic layer was distilled under reduced pressure, and separated by column chromatography using Hex to obtain compound 13 (20 g, yield: 67%).

(91) Synthesis of Compound H1-12

(92) Compound 13 (4.4 g, 13.07 mmol), 7-phenyl-7,9-dihydrobenzo[g]indolo[2,3-b]carbazole (5 g, 13.07 mmol), Pd.sub.2(dba).sub.3 (0.6 g, 0.653 mmol), SPhos (0.5 g, 1.307 mmol), and NaOt-Bu (3.7 g, 39.21 mmol) were added to 70 mL of o-xylene, and the mixture was stirred under reflux for 2 hours. After completion of the reaction, the reaction product was cooled to room temperature, and extracted with MeOH. The extracted product was separated by column chromatography using MC/Hex to obtain compound H1-12 (5.1 g, yield: 60%).

(93) .sup.1H NMR (DMSO-d.sub.6) δ: 9.63 (s, 1H), 9.22 (d, J=8.4 Hz, 1H), 8.64 (dd, J=7.5, 1.2 Hz, 1H), 8.14-8.09 (m, 2H), 8.07 (dt, J=8.1, 0.9 Hz, 1H), 7.94 (d, J=8.9 Hz, 1H), 7.91-7.82 (m, 3H), 7.72 (d, J=2.0 Hz, 1H), 7.67 (d, J=7.6 Hz, 2H), 7.63-7.48 (m, 8H), 7.48-7.41 (m, 2H), 7.40 (d, J=6.1 Hz, 1H), 7.36 (td, J=7.4, 1.0 Hz, 1H), 7.33 (d, J=7.3 Hz, 1H), 7.09 (d, J=49.0 Hz, 2H)

(94) TABLE-US-00015 MW M.P. H1-12 640.7 226.7° C.

EXAMPLE 16: PREPARATION OF COMPOUND H2-3

(95) ##STR00091##

(96) Synthesis of Compound 2-1

(97) 2-chloro-4,6-di(naphthalene-2-yl)-1,3,5-triazine (20 g, 79.7 mmol), (4-bromonaphthalene-1-yl)boronic acid (32.2 g, 87.7 mmol), Pd(PPh.sub.3).sub.4 (4.6 g, 3.985 mmol), and Cs.sub.2CO.sub.3 (65 g, 199.25 mmol) were added to 400 mL of toluene in a flask, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, the reaction product was cooled to room temperature, an organic layer was extracted with ethyl acetate, and the residual moisture was removed with magnesium sulfate. The residue was dried, and separated by column chromatography to obtain compound 2-1 (30 g, yield: 74%).

(98) Synthesis of Compound H2-3

(99) Compound 2-1 (10 g, 19.7 mmol), 9H-carbazole (3.0 g, 17.9 mmol), Pd.sub.2(dba).sub.3 (0.8 g, 0.9 mmol), SPhos (0.73 g, 1.79 mmol), and NaOt-Bu (4.3 g, 44.75 mmol) were dissolved in 90 mL of o-xylene in a flask, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, the reaction product was extracted with ethyl acetate, and separated by column chromatography to obtain compound H2-3 (1.5 g, yield: 13%).

(100) TABLE-US-00016 MW M.P. H2-3 624.15 265° C.

EXAMPLE 17: PREPARATION OF COMPOUND H2-10

(101) ##STR00092##

(102) Synthesis of Compound 2-2

(103) 4-bromo-9H-carbazole (10 g, 40.6 mmol), phenylboronic acid (6.2 g, 48.7 mmol), Pd(PPh.sub.3).sub.4 (2.3 g, 2.03 mmol), and Na.sub.2CO.sub.3 (13 g, 121.8 mmol) were added to 200 mL of toluene, 100 mL of ethanol, and 100 mL of water in a flask, and the mixture was stirred under reflux for 3 hours. After completion of the reaction, the reaction product was cooled to room temperature, an organic layer was extracted with ethyl acetate, and the residual moisture was removed with magnesium sulfate. The residue was dried, and separated by column chromatography to obtain compound 2-2 (9 g, yield: 91%).

(104) Synthesis of Compound H2-10

(105) Compound 2-1 (8.5 g, 13.5 mmol), compound 2-2 (3.0 g, 12.3 mmol), Pd.sub.2(dba).sub.3 (0.56 g, 0.615 mmol), SPhos (0.51 g, 1.23 mmol), and NaOt-Bu (2.9 g, 3075 mmol) were dissolved in 60 mL of o-xylene in a flask, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, the reaction product was extracted with ethyl acetate, and separated by column chromatography to obtain compound H2-10 (2.8 g, yield: 32.5%).

(106) TABLE-US-00017 MW M.P. H2-10 700.85 260.3° C.

EXAMPLE 18: PREPARATION OF COMPOUND H2-8

(107) ##STR00093##

(108) 4-phenyl-9H-carbazole (3.0 g, 12.3 mmol), 2-(4-bromonaphthalene-1-yl)-4,6-diphenyl-1,3,5-triazine (5.4 g, 12.3 mmol), Pd.sub.2(dba).sub.3 (0.56 g, 0.62 mmol), SPhos (0.51 g, 1.23 mmol), and NaOt-Bu (2.4 g, 24.7 mmol) were added to 62 mL of o-xylene in a flask, and the mixture was stirred under reflux for 6 hours. After completion of the reaction, the reaction product was cooled to room temperature, and then MeOH was added thereto while stirring at room temperature. The resulting solid was filtered under reduced pressure, and the filtrate was separated by column chromatography to obtain compound H2-8 (3.3 g, yield: 45%).

(109) TABLE-US-00018 MW M.P. H2-8 600.71 254° C.

EXAMPLE 19: PREPARATION OF COMPOUND H2-2

(110) ##STR00094##

(111) Compound A (8.0 g, 16.4 mmol), 9H-carbazole (3.0 g, 18.0 mmol). Pd.sub.2(dba), (0.9 g, 0.8 mmol), SPhos (0.7 g, 1.64 mmol), and NaOt-Bu (2.4 g, 24.6 mmol) were added to 82 mL of o-xylene in a flask, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, the reaction product was extracted with ethyl acetate, and separated by column chromatography to obtain compound H2-2 (6.0 g, yield: 69%).

(112) TABLE-US-00019 MW M.P. H2-2 524.63 245° C.

EXAMPLE 20: PREPARATION OF COMPOUND H2-11

(113) ##STR00095##

(114) Synthesis of Compound 2-3

(115) 1-bromo-9H-carbazole (10 g, 40.6 mmol), phenylboronic acid (6.2 g, 48.7 mmol), Pd(PPh.sub.3).sub.4 (2.3 g, 2.03 mmol), and Na.sub.2CO.sub.3 (13 g, 121.8 mmol) were added to 200 mL of toluene, 100 mL of ethanol, and 100 mL of water in a flask, and the mixture was stirred under reflux for 3 hours. After completion of the reaction, the reaction product was cooled to room temperature, an organic layer was extracted with ethyl acetate, and the residual moisture was removed with magnesium sulfate. The residue was dried, and separated by column chromatography to obtain compound 2-3 (9 g, yield: 96%).

(116) Synthesis of Compound H2-11

(117) Compound 2-3 (3.0 g, 12.3 mmol), compound A (8 g, 18.5 mmol), Cu powder (0.39 g, 6.15 mmol), and K.sub.2CO.sub.3 (3.4 g, 24.6 mmol) were added to 60 mL of dichlorobenzene (DCB) in a flask, and the mixture was stirred under reflux for 24 hours. After completion of the reaction, the reaction product was cooled to room temperature, and MeOH was added thereto while stirring at room temperature. The resulting solid was filtered under reduced pressure, and the filtrate was separated by column chromatography to obtain compound H2-11 (1.1 g, yield: 14.8%).

(118) TABLE-US-00020 MW M.P. H2-11 600.23 226.9° C.

(119) Hereinafter, the luminous efficiency and lifetime 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 1-3: PRODUCING AN OLED CO-DEPOSITED WITH A FIRST HOST COMPOUND AND A SECOND HOST COMPOUND ACCORDING TO THE PRESENT DISCLOSURE

(120) 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 isopropanol. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 shown in Table 3 below as a first hole injection compound was introduced into a cell of the vacuum vapor deposition apparatus, and compound HT-1 shown in Table 3 below as a first hole transport compound was introduced into another cell of the vacuum vapor deposition apparatus. The two materials were evaporated at different rates to be deposited in a doping amount of the first hole injection compound of 3 wt % based on the total amount of the first hole injection compound and the first hole transport compound to form a first hole injection layer having a thickness of 10 nm on the ITO substrate. Next, compound HT-1 was deposited as a first hole transport layer having a thickness of 80 nm on the first 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 layer 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 below were introduced into two cells of the vacuum vapor depositing apparatus, respectively, as hosts, and compound 0-39 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 as electron transport materials were deposited at a weight ratio of 50:50 on the light-emitting layer to form an electron transport layer having a thickness of 35 nm. After depositing compound EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al 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. All the materials used for producing the OLED were purified by vacuum sublimation at 10.sup.−6 torr.

COMPARATIVE EXAMPLES 1-1 TO 1-3: PRODUCING AN OLED COMPRISING A COMPARATIVE COMPOUND AS A HOST

(121) An OLED was produced in the same manner as in Device Example 1-1, except that the second host compound shown in Table 1 below was solely used as a host of the light-emitting layer.

COMPARATIVE EXAMPLE 1-4: PRODUCING AN OLED COMPRISING A COMPARATIVE COMPOUND AS A HOST

(122) An OLED was produced in the same manner as in Device Example 1-1, except that the first host compound and the second host compound shown in Table 1 below were respectively used as hosts of the light-emitting layer.

(123) The driving voltage, luminous efficiency, and light-emitting color at a luminance of 1,000 nit, and the time taken to reduce from the initial luminance of 100% to a luminance of 95% in a luminance of 5,500 nit (T95) of the OLEDs produced in Device Examples 1-1 to 1-3 and Comparative Examples 1-1 to 1-4, are shown in Table 1 below.

(124) TABLE-US-00021 TABLE 1 Driving Luminous Light- Second Voltage Efficiency Emitting Lifetime First Host Host [V] [cd/A] Color (T 95) [hr] Device Example 1-1 H1-11 H2-3  2.9 32.0 Red 640 Device Example 1-2 H1-11 H2-10 3.1 32.5 Red 524 Device Example 1-3 H1-11 H2-2  3.0 33.8 Red 394 Comparative Example 1-1 — H2-3  3.5 24.7 Red 57.5 Comparative Example 1-2 — H2-10 4.0 25.6 Red 45.9 Comparative Example 1-3 — H2-2  3.3 28.4 Red 52.6 Comparative Example 1-4 H1-11  A-1  3.0 32.3 Red 321

(125) From Table 1 above, it can be confirmed that the organic electroluminescent devices comprising a specific combination of compounds of the present disclosure as host materials have significantly reduced driving voltage and remarkably improved luminous efficiency and lifetime properties as compared with conventional organic electroluminescent devices.

DEVICE EXAMPLES 2-1 TO 2-3: PRODUCING AN OLED ACCORDING TO THE PRESENT DISCLOSURE

(126) An OLED was produced in the same manner as in Device Example 1-1, except that a light-emitting layer was formed as follows: The compound shown in Table 2 below as a host was introduced into a cell of the vacuum vapor deposition apparatus, and compound D-39 was introduced into another cell of the vacuum vapor deposition apparatus as a dopant. The two materials were evaporated at different rates to be deposited in a doping amount of the dopant of 3 wt % based on the total amount of the host and the dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.

COMPARATIVE EXAMPLE 2-1: PRODUCING AN OLED COMPRISING A COMPARATIVE COMPOUND

(127) An OLED was produced in the same manner as in Device Example 2-1, except that compound A-1 shown in Table 3 below was used as a host of the light-emitting layer.

(128) The time taken to reduce from the initial luminance of 100% to a luminance of 95% in a luminance of 5,500 nit (T95) of the OLEDs produced in Device Examples 2-1 to 2-3 and Comparative Example 2-1, are shown in Table 2 below.

(129) TABLE-US-00022 TABLE 2 Host Lifetime (T95) [hr] Device Example 2-1 H2-3 57.5 Device Example 2-2 H2-10 45.9 Device Example 2-3 H2-2 52.6 Comparative Example  A-1 27.3 2-1

(130) From Table 2 above, it can be confirmed that the organic electroluminescent devices comprising the compounds according to the present disclosure as host materials have longer lifetime properties as compared with conventional organic electroluminescent devices.

(131) The compounds used in the Device Examples and the Comparative Examples are shown in Table 3 below.

(132) TABLE-US-00023 TABLE 3 Hole Injection Layer/ Hole Transport Layer Light-Emitting Layer 00 01 02 03 04 Electron transport Layer/ Electron Injection Layer 05 06