ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE INCLUDING THE SAME

Abstract

Disclosed are an anthracene derivative with a specific structure and an organic electroluminescent device including the anthracene derivative. The organic electroluminescent device includes a light emitting layer employing the anthracene derivative as a host compound and a polycyclic aromatic derivative with a specific structure as a dopant compound. The use of the host and dopant compounds allows the organic electroluminescent device to have a long lifetime and significantly improved low-voltage characteristics.

Claims

1. An anthracene derivative represented by Formula A: ##STR00105## wherein Ar.sub.1 is selected from substituted or unsubstituted C.sub.6-C.sub.50 aryl, substituted or unsubstituted C.sub.2-C.sub.50 heteroaryl, and substituted or unsubstituted C.sub.3-C.sub.50 mixed aliphatic-aromatic cyclic groups, R.sub.1 to R.sub.14 are identical to or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C.sub.1-C.sub.30 alkyl, substituted or unsubstituted C.sub.6-C.sub.50 aryl, substituted or unsubstituted C.sub.2-C.sub.30 alkenyl, substituted or unsubstituted C.sub.2-C.sub.30 alkynyl, substituted or unsubstituted C.sub.3-C.sub.30 cycloalkyl, substituted or unsubstituted C.sub.3-C.sub.30 cycloalkenyl, substituted or unsubstituted C.sub.2-C.sub.50 heteroaryl, substituted or unsubstituted C.sub.2-C.sub.30 heterocycloalkyl, substituted or unsubstituted C.sub.1-C.sub.30 alkoxy, substituted or unsubstituted C.sub.6-C.sub.50 aryloxy, substituted or unsubstituted C.sub.1-C.sub.30 alkylthioxy, substituted or unsubstituted C.sub.6-C.sub.50 arylthioxy, substituted or unsubstituted C.sub.1-C.sub.30 alkylamine, substituted or unsubstituted C.sub.6-C.sub.50 arylamine, substituted or unsubstituted C.sub.1-C.sub.30 alkylsilyl, substituted or unsubstituted C.sub.6-C.sub.50 arylsilyl, substituted or unsubstituted C.sub.3-C.sub.50 mixed aliphatic-aromatic cyclic groups, cyano, nitro, and halogen, with the proviso that one of R.sub.9 and R.sub.10 is bonded to L.sub.1, X is an oxygen (O) or sulfur atom (S), L.sub.1 is a divalent linker and is a single bond or is selected from substituted or unsubstituted C.sub.6-C.sub.50 arylene, substituted or unsubstituted C.sub.2-C.sub.50 heteroarylene, and substituted or unsubstituted C.sub.3-C.sub.50 mixed aliphatic-aromatic cyclic groups, and n is an integer from 1 to 3, provided that when n is 2 or more, the linkers L.sub.1 are identical to or different from each other, the “substituted” in the definition of Ar.sub.1, R.sub.1 to R.sub.14, and L.sub.1 indicating substitution with one or more substituents selected from deuterium, cyano, halogen, hydroxyl, nitro, alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, heteroalkyl, aryl, arylalkyl, alkylaryl, heteroaryl, heteroarylalkyl, alkoxy, alkylamino, arylamino, heteroarylamino, alkylsilyl, arylsilyl, aryloxy, and mixed aliphatic-aromatic cyclic groups, and wherein the anthracene derivative represented by Formula A comprises at least one deuterium atom (D).

2. The anthracene derivative according to claim 1, wherein the anthracene derivative represented by Formula A is a compound represented by Formula A-1: ##STR00106## wherein Ar.sub.11 is selected from substituted or unsubstituted C.sub.6-C.sub.50 aryl, substituted or unsubstituted C.sub.2-C.sub.50 heteroaryl, and substituted or unsubstituted C.sub.3-C.sub.50 mixed aliphatic-aromatic cyclic groups, R.sub.21 to R.sub.33 are identical to or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C.sub.1-C.sub.30 alkyl, substituted or unsubstituted C.sub.6-C.sub.50 aryl, substituted or unsubstituted C.sub.2-C.sub.30 alkenyl, substituted or unsubstituted C.sub.2-C.sub.30 alkynyl, substituted or unsubstituted C.sub.3-C.sub.30 cycloalkyl, substituted or unsubstituted C.sub.3-C.sub.30 cycloalkenyl, substituted or unsubstituted C.sub.2-C.sub.50 heteroaryl, substituted or unsubstituted C.sub.2-C.sub.30 heterocycloalkyl, substituted or unsubstituted C.sub.1-C.sub.30 alkoxy, substituted or unsubstituted C.sub.6-C.sub.50 aryloxy, substituted or unsubstituted C.sub.1-C.sub.30 alkylthioxy, substituted or unsubstituted C.sub.6-C.sub.50 arylthioxy, substituted or unsubstituted C.sub.1-C.sub.30 alkylamine, substituted or unsubstituted C.sub.6-C.sub.50 arylamine, substituted or unsubstituted C.sub.1-C.sub.30 alkylsilyl, substituted or unsubstituted C.sub.6-C.sub.50 arylsilyl, substituted or unsubstituted C.sub.3-C.sub.50 mixed aliphatic-aromatic cyclic groups, cyano, nitro, and halogen, X is an oxygen (O) or sulfur atom (S), L.sub.2 is a divalent linker and is a single bond or is selected from substituted or unsubstituted C.sub.6-C.sub.50 arylene, substituted or unsubstituted C.sub.2-C.sub.50 heteroarylene, and substituted or unsubstituted C.sub.3-C.sub.50 mixed aliphatic-aromatic cyclic groups, and m is an integer from 1 to 3, provided that when m is 2 or more, the linkers L.sub.1 are identical to or different from each other, the “substituted” in the definition of Ar.sub.11, R.sub.21 to R.sub.33, and L.sub.2 indicating substitution with one or more substituents selected from deuterium, cyano, halogen, hydroxyl, nitro, alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, heteroalkyl, aryl, arylalkyl, alkylaryl, heteroaryl, heteroarylalkyl, alkoxy, alkylamino, arylamino, heteroarylamino, alkylsilyl, arylsilyl, aryloxy, and mixed aliphatic-aromatic cyclic groups, or Formula A-2: ##STR00107## wherein Ar.sub.11, R.sub.21 to R.sub.33, X, L.sub.2, and m are as defined in Formula A-1, and wherein each of the compounds represented by Formulae A-1 and A-2 comprises at least one deuterium atom (D).

3. The anthracene derivative according to claim 1, wherein at least one of Rn to R.sub.14 in Formula A is selected from substituted or unsubstituted C.sub.6-C.sub.20 aryl, substituted or unsubstituted C.sub.3-C.sub.20 cycloalkyl, and substituted or unsubstituted C.sub.3-C.sub.20 heteroaryl.

4. The anthracene derivative according to claim 3, wherein at least one of R.sub.11 to R.sub.14 in Formula A is substituted or unsubstituted deuterated C.sub.6-C.sub.20 aryl, substituted or unsubstituted deuterated C.sub.3-C.sub.20 cycloalkyl or substituted or unsubstituted deuterated C.sub.3-C.sub.20 heteroaryl.

5. The anthracene derivative according to claim 2, wherein each of R.sub.29 in Formula A-1 and R.sub.29 in Formula A-2 is substituted or unsubstituted deuterated C.sub.6-C.sub.20 aryl, substituted or unsubstituted deuterated C.sub.3-C.sub.20 cycloalkyl or substituted or unsubstituted deuterated C.sub.3-C.sub.20 heteroaryl which comprises at least one deuterium atom (D).

6. The anthracene derivative according to claim 1, wherein the degree of deuteration of the anthracene derivative represented by Formula A is at least 10%.

7. The anthracene derivative according to claim 1, wherein the degree of deuteration of the anthracene derivative represented by Formula A is at least 30%.

8. The anthracene derivative according to claim 1, wherein the anthracene derivative represented by Formula A is selected from the following compounds 1 to 104: ##STR00108## ##STR00109## ##STR00110## ##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118## ##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127## ##STR00128## ##STR00129## ##STR00130## ##STR00131## ##STR00132## ##STR00133##

9. An organic electroluminescent device comprising a first electrode, a second electrode opposite to the first electrode, and one or more organic layers interposed between the first and second electrodes wherein one of the organic layers comprises the anthracene derivative represented by Formula A according to claim 1.

10. The organic electroluminescent device according to claim 9, wherein the organic layers comprise one or more layers selected from a hole injecting layer, a hole transport layer, a functional layer having functions of both hole injection and hole transport, alight emitting layer, an electron transport layer, and an electron injecting layer.

11. The organic electroluminescent device according to claim 10, wherein one of the organic layers interposed between the first and second electrodes is a light emitting layer composed of a host and a dopant and the anthracene derivative represented by Formula A is used as the host.

12. The organic electroluminescent device according to claim 11, wherein one or more host compounds other than the host compound represented by Formula A are mixed or stacked in the light emitting layer.

13. The organic electroluminescent device according to claim 11, wherein the dopant is represented by Formula D-1: ##STR00134## wherein X.sub.1 is selected from B, P═O, and P═S, Y.sub.1 to Y.sub.3 are each independently selected from NR.sub.41, CR.sub.42R.sub.43, O, S, Se, and SiR.sub.44R.sub.45, R.sub.41 to R.sub.45 are identical to or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C.sub.1-C.sub.30 alkyl, substituted or unsubstituted C.sub.6-C.sub.50 aryl, substituted or unsubstituted C.sub.3-C.sub.30 cycloalkyl, substituted or unsubstituted C.sub.3-C.sub.30 heterocycloalkyl, substituted or unsubstituted C.sub.2-C.sub.50 heteroaryl, substituted or unsubstituted C.sub.1-C.sub.30 alkoxy, substituted or unsubstituted C.sub.6-C.sub.30 aryloxy, substituted or unsubstituted C.sub.1-C.sub.30 alkylthioxy, substituted or unsubstituted C.sub.6-C.sub.30 arylthioxy, substituted or unsubstituted C.sub.1-C.sub.30 alkylamine, substituted or unsubstituted C.sub.6-C.sub.30 arylamine, substituted or unsubstituted C.sub.2-C.sub.30 heteroarylamine, substituted or unsubstituted C.sub.1-C.sub.30 alkylsilyl, substituted or unsubstituted C.sub.6-C.sub.30 arylsilyl, substituted or unsubstituted C.sub.3-C.sub.20 mixed aliphatic-aromatic cyclic groups, nitro, cyano, and halogen, with the proviso that each of R.sub.41 to R.sub.45 is optionally bonded to one or more of the rings A.sub.1 to A.sub.3 to form an alicyclic or aromatic monocyclic or polycyclic ring and that R.sub.42 and R.sub.43 together and R.sub.44 and R.sub.45 together optionally form an alicyclic or aromatic monocyclic or polycyclic ring, and A.sub.1 to A.sub.3 are each independently selected from substituted or unsubstituted C.sub.6-C.sub.50 aromatic hydrocarbon rings, substituted or unsubstituted C.sub.2-C.sub.50 heteroaromatic rings, substituted or unsubstituted C.sub.3-C.sub.30 aliphatic rings, and unsubstituted or unsubstituted C.sub.3-C.sub.30 mixed aliphatic-aromatic cyclic groups, with the proviso that the substituents of each of the rings A.sub.1 to A.sub.3 together optionally form an alicyclic or aromatic monocyclic or polycyclic ring, the “substituted” in the definition of A.sub.1 to A.sub.3 and R.sub.41 to R.sub.45 indicating substitution with one or more substituents selected from deuterium, cyano, halogen, hydroxyl, nitro, alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, heteroalkyl, aryl, arylalkyl, alkylaryl, heteroaryl, heteroarylalkyl, alkoxy, alkylamino, arylamino, heteroarylamino, alkylsilyl, arylsilyl, aryloxy, and mixed aliphatic-aromatic cyclic groups, or Formula D-2: ##STR00135## wherein X.sub.1, Y.sub.1 to Y.sub.3, R.sub.41 to R.sub.45, and A.sub.1 to A.sub.3 are as defined in Formula D-1.

14. The organic electroluminescent device according to claim 10, wherein the organic electroluminescent device is used in a display or lighting system selected from flat panel displays, flexible displays, monochromatic flat panel lighting systems, white flat panel lighting systems, flexible monochromatic lighting systems, flexible white lighting systems, displays for automotive applications, displays for virtual reality, and displays for augmented reality.

Description

SYNTHESIS EXAMPLE 1. SYNTHESIS OF COMPOUND 43

Synthesis Example 1-1. Synthesis of Intermediate 1-a

[0077] ##STR00062##

[0078] Bromobenzene(d5) (60.4 g, 0.373 mol) and 480 mL of tetrahydrofuran were cooled to −78° C. and stirred in a 2 L reactor. To the cold solution was added dropwise n-butyllithium (223.6 mL, 0.357 mol). The mixture was stirred at the same temperature for 1 h. To the resulting reaction solution was added dropwise a solution of o-phthalaldehyde (20 g, 0.149 mol) in 100 mL of tetrahydrofuran, followed by stirring at room temperature. The reaction was quenched with 200 mL of an aqueous ammonium chloride solution. The reaction solution was extracted with ethyl acetate, concentrated under reduced pressure, and purified by column chromatography to afford Intermediate 1-a (40 g, 89%).

Synthesis Example 1-2: Synthesis of Intermediate 1-b

[0079] ##STR00063##

[0080] Intermediate 1-a (40 g, 0.133 mol) was dissolved in 200 mL of acetic acid and stirred in a 500 mL reactor. To the solution was added dropwise 2 mL of hydrogen bromide. The mixture was stirred at 80° C. for 2 h. After completion of the reaction, the reaction solution was cooled to room temperature. The reaction solution was slowly poured into a beaker containing 500 mL of distilled water, followed by stirring. The resulting solid was filtered, washed with distilled water, and purified by column chromatography to afford Intermediate 1-b (13 g, 37%).

Synthesis Example 1-3: Synthesis of Intermediate 1-c

[0081] ##STR00064##

[0082] Intermediate 1-b (13.0 g, 0.049 mol) was dissolved in 130 mL of N,N-dimethylamide in a 500 mL reactor. The solution was stirred at room temperature. To the solution was added dropwise a solution of N-bromosuccinimide (10.54 g, 0.059 mol) in 40 mL of N,N-dimethylamide. The completion of the reaction was confirmed by thin layer chromatography. The reaction solution was poured into a beaker containing 500 mL of distilled water, followed by stirring. The resulting solid was filtered, washed with distilled water, and purified by column chromatography to afford Intermediate 1-c (14 g, 83%).

Synthesis Example 1-4: Synthesis of Intermediate 1-d

[0083] ##STR00065##

[0084] Intermediate 1-c (50 g, 0.146 mol) were dissolved in 500 mL of tetrahydrofuran in a 500 mL reactor. The solution was cooled to −78° C. and n-butyllithium (100 mL, 0.161 mol) was added dropwise thereto. The mixture was stirred for 5 h. To the mixture was added trimethyl borate (18 mL, 0.161 mol), followed by stirring at room temperature overnight. After completion of the reaction, the reaction mixture was acidified with 2 N hydrochloric acid and recrystallized to yield Intermediate 1-d (25 g, 56%).

Synthesis Example 1-5: Synthesis of Intermediate 1-e

[0085] ##STR00066##

[0086] Intermediate 1-d (30 g, 0.098 mol), (4-bromophenyl)boronic acid (23.5 g, 0.117 mol), palladium acetate (0.4 g, 0.002 mol), potassium carbonate (27 g, 0.195 mol), and Sphos (1.6 g, 0.004 mol) were placed in a 500 mL reactor, and 200 mL of toluene, 90 mL of ethanol, and 60 mL of distilled water were added thereto. The temperature of the reactor was raised to 90° C., followed by stirring overnight. After completion of the reaction, the temperature of the reactor was lowered to room temperature. The reaction mixture was extracted with methanol. The organic layer was separated, concentrated under reduced pressure, purified by column chromatography, and recrystallized from toluene and acetone to yield Intermediate 1-e (12 g, 32%).

Synthesis Example 1-6: Synthesis of Compound 43

[0087] ##STR00067##

[0088] Compound 43 (yield 30%) was synthesized in the same manner as in Synthesis Example 1-5, except that Intermediate 1-e and 2-bromo-3-phenylbenzofuran were used instead of Intermediate 1-d and (4-bromophenyl)boronic acid, respectively.

[0089] MS (MALDI-TOF): m/z 531.25 [M.sup.+]

SYNTHESIS EXAMPLE 2. SYNTHESIS OF COMPOUND 56

Synthesis Example 2-1: Synthesis of Intermediate 2-a

[0090] ##STR00068##

[0091] 5-Bromobenzofuran (30 g, 0.152 mol), (phenyl-d5)boronic acid (23.2 g, 0.183 mol), tetrakis(triphenylphosphine)palladium(0) (5.3 g, 0.005 mol), potassium carbonate (42.1 g, 0.305 mol), 300 mL of THF, and 120 mL of distilled water were placed in a 500 mL reactor. The mixture was stirred under reflux for 12 h. After completion of the reaction, the reaction solution was allowed to stand for layer separation. The organic layer was concentrated under reduced pressure and purified by column chromatography to afford Intermediate 2-a (21.2 g, 70%).

Synthesis Example 2-2: Synthesis of Intermediate 2-b

[0092] ##STR00069##

[0093] Intermediate 2-a (21.2 g, 0.106 mol) and dichloromethane were placed in a 500 mL reactor. The mixture was cooled to −10° C. and bromine was added thereto. The resulting mixture was stirred for 1 h. To the reaction mixture was added an aqueous sodium thiosulfate solution, followed by stirring. The mixture was allowed to stand for layer separation. The organic layer was concentrated under reduced pressure, added with ethanol, cooled to −10° C., and added with an ethanolic solution of potassium hydroxide. The mixture was heated to reflux for 4 h. After completion of the reaction, the reaction solution was allowed to stand for layer separation. The organic layer was concentrated under reduced pressure and purified by column chromatography to afford Intermediate 2-b (20 g, 70%).

Synthesis Example 2-3: Synthesis of Compound 56

[0094] ##STR00070##

[0095] Intermediate 2-b (20 g, 0.072 mol), 10-phenyl-anthracene-9-boronic acid (25.7 g, 0.086 mol), tetrakis(triphenylphosphine)palladium(0) (2.5 g, 0.002 mol), potassium carbonate (29.8 g, 0.216 mol), 140 mL of toluene, 60 mL of ethanol, and 60 mL of distilled water were refluxed for 12 h. After completion of the reaction, the reaction solution was allowed to stand for layer separation. The organic layer was concentrated under reduced pressure, purified by column chromatography, and recrystallized to give Compound 56 (10 g, 32%).

[0096] MS (MALDI-TOF): m/z 451.20 [M.sup.+]

SYNTHESIS EXAMPLE 3. SYNTHESIS OF COMPOUND 58

Synthesis Example 3-1: Synthesis of Intermediate 3-a

[0097] ##STR00071##

[0098] Intermediate 3-a (yield 77%) was synthesized in the same manner as in Synthesis Example 2-1, except that phenylboronic acid was used instead of (phenyl-d5)boronic acid.

Synthesis Example 3-2: Synthesis of Intermediate 3-b

[0099] ##STR00072##

[0100] Intermediate 3-b (yield 70%) was synthesized in the same manner as in Synthesis Example 2-2, except that Intermediate 3-a was used instead of Intermediate 2-a.

Synthesis Example 3-3: Synthesis of Intermediate 3-c

[0101] ##STR00073##

[0102] Intermediate 3-c (yield 74%) was synthesized in the same manner as in Synthesis Example 2-3, except that Intermediate 3-b and 4-(10-phenyl-9-anthryl)phenylboronic acid were used instead of Intermediate 2-b and 10-phenyl-anthracene-9-boronic acid, respectively.

Synthesis Example 3-4: Synthesis of Intermediate 3-d

[0103] ##STR00074##

[0104] Intermediate 3-c (20 g, 0.038 mol) and 250 mL of THF were cooled to −50° C. in a 500 mL reactor and n-butyllithium (1.6 M) was added thereto. After 1 h, iodine was slowly added. The temperature was gradually raised to room temperature. To the mixture was added an aqueous sodium thiosulfate solution at room temperature. The resulting mixture was allowed to stand for layer separation. The organic layer was concentrated under reduced pressure and purified by column chromatography to afford Intermediate 3-d (16 g, 65%).

Synthesis Example 3-5: Synthesis of Compound 58

[0105] ##STR00075##

[0106] Compound 58 (yield 50%) was synthesized in the same manner as in Synthesis Example 2-3, except that Intermediate 3-d and (phenyl-d5)boronic acid were used instead of Intermediate 2-b and 10-phenyl-anthracene-9-boronic acid, respectively.

[0107] MS (MALDI-TOF): m/z 603.26 [M.sup.+]

SYNTHESIS EXAMPLE 4. SYNTHESIS OF COMPOUND 61

Synthesis Example 4-1: Synthesis of Intermediate 4-a

[0108] ##STR00076##

[0109] Intermediate 4-a (yield 71%) was synthesized in the same manner as in Synthesis Example 2-3, except that 4-bromophenylboronic acid was used instead of 10-phenyl-anthracene-9-boronic acid.

Synthesis Example 4-2: Synthesis of Compound 61

[0110] ##STR00077##

[0111] Compound 61 (yield 30%) was synthesized in the same manner as in Synthesis Example 2-3, except that Intermediate 4-a and 10-phenyl (d5)-anthracene-9-boronic acid were used instead of Intermediate 2-b and 10-phenyl-anthracene-9-boronic acid, respectively.

[0112] MS (MALDI-TOF): m/z 532.26 [M.sup.+]

SYNTHESIS EXAMPLE 5. SYNTHESIS OF COMPOUND 66

Synthesis Example 5-1: Synthesis of Compound 66

[0113] ##STR00078##

[0114] Compound 66 (yield 30%) was synthesized in the same manner as in Synthesis Example 2-3, except that 3-bromo-2-naphthalen-1-yl benzofuran and 10-phenyl(d5)-anthracene-9-boronic acid were used instead of Intermediate 2-b and 10-phenyl-anthracene-9-boronic acid, respectively.

[0115] MS (MALDI-TOF): m/z 501.21 [M.sup.+]

SYNTHESIS EXAMPLE 6. SYNTHESIS OF COMPOUND 14

Synthesis Example 6-1: Synthesis of Intermediate 6-a

[0116] ##STR00079##

[0117] 7-Chlorobenzo[b]thiophene (30 g, 0.178 mol) and DMF were stirred in a 500 mL reactor and NBS was added thereto. The mixture was refluxed with stirring for 6 h. Distilled water was added to the reaction solution. The resulting mixture was allowed to stand for layer separation. The organic layer was concentrated under reduced pressure and purified by column chromatography to afford Intermediate 6-a (27 g, 62%).

Synthesis Example 6-2: Synthesis of Intermediate 6-b

[0118] ##STR00080##

[0119] Intermediate 6-b (yield 70%) was synthesized in the same manner as in Synthesis Example 2-1, except that Intermediate 6-a and phenylboronic acid were used instead of 5-bromobenzofuran and (phenyl-d5)boronic acid, respectively.

Synthesis Example 6-3: Synthesis of Intermediate 6-c

[0120] ##STR00081##

[0121] Intermediate 6-c (yield 70%) was synthesized in the same manner as in Synthesis Example 3-4, except that Intermediate 6-b was used instead of Intermediate 3-c.

Synthesis Example 6-4: Synthesis of Intermediate 6-d

[0122] ##STR00082##

[0123] Intermediate 6-d (yield 68%) was synthesized in the same manner as in Synthesis Example 2-3, except that Intermediate 6-c and 10-phenyl(d5)-anthracene-9-boronic acid were used instead of Intermediate 2-b and 10-phenyl-anthracene-9-boronic acid, respectively.

Synthesis Example 6-5: Synthesis of Compound 14

[0124] ##STR00083##

[0125] Compound 14 (yield 33%) was synthesized in the same manner as in Synthesis Example 2-3, except that Intermediate 6-d and dibenzo[b,d]furan-1-ylboronic acid were used instead of Intermediate 2-b and 10-phenyl-anthracene-9-boronic acid, respectively.

[0126] MS (MALDI-TOF): m/z 633.22 [M.sup.+]

SYNTHESIS EXAMPLE 7. SYNTHESIS OF COMPOUND 89

Synthesis Example 7-1: Synthesis of Intermediate 7-a

[0127] ##STR00084##

[0128] Intermediate 7-a (yield 70%) was synthesized in the same manner as in Synthesis Example 3-3, except that 10-(phenyl-d5)-anthracene-9-boronic acid was used instead of 4-(10-phenyl-9-anthryl)phenylboronic acid.

Synthesis Example 7-2: Synthesis of Intermediate 7-b

[0129] ##STR00085##

[0130] Intermediate 7-b (yield 63%) was synthesized in the same manner as in Synthesis Example 3-4, except that Intermediate 7-a was used instead of Intermediate 3-c.

Synthesis Example 7-3: Synthesis of Compound 89

[0131] ##STR00086##

[0132] Compound 89 (yield 51%) was synthesized in the same manner as in Synthesis Example 3-5, except that Intermediate 7-b and phenylboronic acid were used instead of Intermediate 3-d and (phenyl-d5)boronic acid, respectively.

[0133] MS (MALDI-TOF): m/z 527.23 [M.sup.+]

SYNTHESIS EXAMPLE 8. SYNTHESIS OF COMPOUND 90

Synthesis Example 8-1: Synthesis of Intermediate 8-a

[0134] ##STR00087##

[0135] Intermediate 8-a (yield 55%) was synthesized in the same manner as in Synthesis Example 1-4, except that (anthracene-d8)-9-bromo-10-(phenyl-d5) was used instead of Intermediate 1-c.

Synthesis Example 8-2: Synthesis of Intermediate 8-b

[0136] ##STR00088##

[0137] Intermediate 8-b (yield 55%) was synthesized in the same manner as in Synthesis Example 2-3, except that Intermediate 8-a was used instead of 10-phenyl-anthracene-9-boronic acid.

Synthesis Example 8-3: Synthesis of Intermediate 8-c

[0138] ##STR00089##

[0139] Intermediate 8-c (yield 67%) was synthesized in the same manner as in Synthesis Example 3-4, except that Intermediate 8-b was used instead of Intermediate 3-c.

Synthesis Example 8-4: Synthesis of Compound 90

[0140] ##STR00090##

[0141] Compound 90 (yield 47%) was synthesized in the same manner as in Synthesis Example 7-3, except that Intermediate 8-c was used instead of Intermediate 7-b.

[0142] MS (MALDI-TOF): m/z 540.31 [M.sup.+]

SYNTHESIS EXAMPLE 9. SYNTHESIS OF COMPOUND 91

Synthesis Example 9-1: Synthesis of Intermediate 9-a

[0143] ##STR00091##

[0144] Bromobenzyl bromide (20 g, 0.08 mol), (phenyl-d5)boronic acid (10 g, 0.078 mol), sodium carbonate (10 g, 0.1 mol), and tetrakis(triphenylphosphine)palladium(0) (1.8 g, 0.002 mol) were placed in a 500 mL reactor. The mixture was heated to reflux at 50° C. After 1 h, distilled water was added to the reaction solution, followed by stirring. The resulting mixture was allowed to stand for layer separation. The organic layer was filtered, washed with toluene, and concentrated under reduced pressure. Thereafter, the concentrate was purified by column chromatography to afford Intermediate 9-a (16 g, 82%).

Synthesis Example 9-2: Synthesis of Intermediate 9-b

[0145] ##STR00092##

[0146] Intermediate 9-a (20 g, 0.08 mol) and 200 mL of THF were cooled to −78° C. in a 500 mL reactor and n-butyllithium (1.6 M) was added thereto. To the mixture was slowly added trimethyl borate. The temperature was gradually raised to room temperature. To the resulting mixture was added a 2 M aqueous HCl solution, followed by stirring for 20 min. The reaction mixture was allowed to stand for layer separation. The organic layer was washed with distilled water, concentrated, and recrystallized from THF and heptane to afford Intermediate 9-b (11 g, 63%).

Synthesis Example 9-3: Synthesis of Intermediate 9-c

[0147] ##STR00093##

[0148] Intermediate 9-b (15 g, 0.07 mol), cesium carbonate (34 g, 0.1 mol), tetrakis(triphenylphosphine)palladium(0) (2.4 g, 0.002 mol), and 150 mL of toluene were stirred in a 500 mL reactor. After dropwise addition of 1,1′-(biphenyl-d5)-2-carbonyl chloride (20 g, 0.09 mol), the mixture was heated to reflux at 110° C. After 2 h, toluene and distilled water were added to the reaction solution, followed by stirring. The mixture was allowed to stand for layer separation. The organic layer was concentrated under reduced pressure and purified by column chromatography to afford Intermediate 9-c (14 g, 57%).

Synthesis Example 9-4: Synthesis of Intermediate 9-d

[0149] ##STR00094##

[0150] Intermediate 9-c (20 g, 0.06 mol), In(OTf).sub.3 (3.1 g, 0.006 mol), and 120 mL of dichlorobenzene were heated to reflux at 110° C. in a 500 mL reactor. After 24 h, the reaction solution was filtered through Celite at 50° C. and washed with MC. The organic layer was concentrated under reduced pressure and purified by column chromatography. Subsequent recrystallization afforded Intermediate 9-d (8 g, 43%).

Synthesis Example 9-5: Synthesis of Intermediate 9-e

[0151] ##STR00095##

[0152] Intermediate 9-d (30 g, 0.09 mol) and 300 mL of DMF were stirred in a 500 mL reactor. Thereafter, the mixture was cooled to 0° C. and NBS (16 g, 0.09 mol) was added thereto. The temperature was raised to room temperature. After 3 h stirring, to the resulting mixture was added distilled water. Stirring was continued. The reaction mixture was filtered, washed, purified by column chromatography, and recrystallized from methanol to afford Intermediate 9-e (33 g, 89%).

Synthesis Example 9-6: Synthesis of Intermediate 9-f

[0153] ##STR00096##

[0154] Intermediate 9-f (yield 53%) was synthesized in the same manner as in Synthesis Example 1-4, except that Intermediate 9-e was used instead of Intermediate 1-c.

Synthesis Example 9-7: Synthesis of Compound 91

[0155] ##STR00097##

[0156] Compound 91 (yield 52%) was synthesized in the same manner as in Synthesis Example 1-5, except that Intermediate 9-f and 3-bromo-2-phenylbenzofuran were used instead of Intermediate 1-d and (4-bromophenyl)boronic acid, respectively.

[0157] MS (MALDI-TOF): m/z 531.25 [M.sup.+]

SYNTHESIS EXAMPLE 10. SYNTHESIS OF COMPOUND 92

Synthesis Example 10-1: Synthesis of Intermediate 10-a

[0158] ##STR00098##

[0159] Intermediate 10-a (yield 52%) was synthesized in the same manner as in Synthesis Example 2-3, except that (anthracene-d8)-9-bromo-10-(1,1-biphenyl) was used instead of Intermediate 1-c.

Synthesis Example 10-2: Synthesis of Intermediate 10-b

[0160] ##STR00099##

[0161] Intermediate 10-b (yield 54%) was synthesized in the same manner as in Synthesis Example 2-3, except that Intermediate 10-a was used instead of 10-phenyl-anthracene-9-boronic acid.

Synthesis Example 10-3: Synthesis of Intermediate 10-c

[0162] ##STR00100##

[0163] Intermediate 10-c (yield 64%) was synthesized in the same manner as in Synthesis Example 3-4, except that Intermediate 10-b was used instead of Intermediate 3-c.

Synthesis Example 10-4: Synthesis of Compound 92

[0164] ##STR00101##

[0165] Compound 92 (yield 45%) was synthesized in the same manner as in Synthesis Example 7-3, except that Intermediate 8-c was used instead of Intermediate 7-b.

[0166] MS (MALDI-TOF): m/z 611.31 [M.sup.+]

Examples 1 to 10: Fabrication of Organic Electroluminescent Devices

[0167] ITO glass was patterned to have a light emitting area of 2 mm×2 mm, followed by cleaning. After the cleaned ITO glass was mounted in a vacuum chamber, the base pressure was adjusted to 1×10.sup.−7 torr. DNTPD (700 Å) and α-NPD (300 Å) were deposited in this order on the ITO glass. A mixture of the inventive host compound and the dopant compound shown in Table 1 was used to form a 300 Å thick light emitting layer. Thereafter, the compound of Formula E-1 and the compound of Formula E-2 were used in a ratio of 1:1 to form a 300 Å thick electron transport layer on the light emitting layer. The compound of Formula E-2 was used to form a 10 Å thick electron injecting layer on the electron transport layer. Al was deposited on the electron injecting layer to form a 1000 Å thick Al electrode, completing the fabrication of an organic electroluminescent device. The luminescent properties of the organic electroluminescent device were measured at 10 mA/cm.sup.2.

##STR00102##

Comparative Examples 1 to 6

[0168] Organic electroluminescent devices were fabricated in the same manner as in Examples 1-10, except that BH1, BH2, BH3, BH4, BH5 or BH6 was used instead of the host compound. The luminescent properties of the organic electroluminescent devices were measured at 10 mA/cm.sup.2. The structures of BH1, BH2, BH3, BH4, BH5, and BH6 are as follow:

##STR00103## ##STR00104##

TABLE-US-00001 TABLE 1 Current density Voltage Lifetime Example No. Host Dopant (mA/cm.sup.2) (V) (T97, hr) Example 1 14 D-102 10 3.5 73 Example 2 43 D-102 10 3.5 110 Example 3 56 D-102 10 3.4 93 Example 4 58 D-102 10 3.3 86 Example 5 61 D-102 10 3.3 128 Example 6 66 D-102 10 3.4 113 Example 7 89 D-102 10 3.3 120 Example 8 90 D-102 10 3.4 147 Example 9 91 D-102 10 3.5 127 Example 10 92 D-102 10 3.4 138 Comparative BH1 D-102 10 3.6 55 Example 1 Comparative BH2 D-102 10 3.4 42 Example 2 Comparative BH3 D-102 10 3.5 50 Example 3 Comparative BH4 D-102 10 3.6 34 Example 4 Comparative BH5 D-102 10 3.9 35 Example 5 Comparative BH6 D-102 10 4.0 47 Example 6

[0169] As can be seen from the results in Table 1, the organic electroluminescent devices of Examples 1-10, each of which employed the inventive compound as a host compound for the light emitting layer, showed significantly improved life characteristics (including long lifetimes) and low-voltage characteristics compared to the devices of Comparative Examples 1-6, which employed BH1, BH2, BH3, BH4, BH5, and BH6, respectively, whose structures are different from the specific structures of the host compounds employed in the organic electroluminescent devices of Examples 1-10.