POLYCYCLIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME

Abstract

Disclosed is a polycyclic compound that can be employed in various organic layers of an organic electroluminescent device. The polycyclic compound has a characteristic skeleton structure and characteristic substituents. Also disclosed is an organic electroluminescent device including the polycyclic compound. The organic electroluminescent device includes a light emitting layer employing the polycyclic compound as a dopant and an anthracene derivative having a characteristic structure as a host. The use of the polycyclic compound significantly improves the luminous efficiency and life characteristics of the organic electroluminescent device and makes the organic electroluminescent device highly efficient and long lasting.

Claims

1. A compound represented by Formula A-1: ##STR00323## wherein each Z is independently CR or N, R and R.sub.12 to R.sub.16 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.2-C.sub.30 alkenyl, substituted or unsubstituted C.sub.2-C.sub.30 alkynyl, 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 cycloalkenyl, substituted or unsubstituted C.sub.1-C.sub.30 heterocycloalkyl, substituted or unsubstituted C.sub.2-C.sub.50 heteroaryl, substituted or unsubstituted C.sub.6-C.sub.50 fused polycyclic non-aromatic hydrocarbon rings, substituted or unsubstituted C.sub.2-C.sub.50 fused polycyclic non-aromatic heterocyclic rings, 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.5-C.sub.30 arylthioxy, substituted or unsubstituted amine, substituted or unsubstituted silyl, substituted or unsubstituted germanium, substituted or unsubstituted boron, substituted or unsubstituted aluminum, phosphoryl, hydroxyl, selenium, tellurium, nitro, cyano, and halogen, with the proviso that each of R.sub.12 to R.sub.16 optionally forms an aliphatic or aromatic monocyclic or polycyclic ring with the other adjacent group(s), the moieties Z are identical to or different from each other, the groups R are identical to or different from each other, with the proviso that the groups R are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, Y.sub.1 is O or S, Y.sub.2 and Y.sub.3 are identical to or different from each other and are each independently selected from N—R.sub.1, CR.sub.2R.sub.3, O, S, Se, and SiR.sub.4R.sub.5, R.sub.1 to R.sub.5 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.2-C.sub.30 alkynyl, substituted or unsubstituted C.sub.2-C.sub.30 alkenyl, 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 cycloalkenyl, substituted or unsubstituted C.sub.1-C.sub.30 heterocycloalkyl, substituted or unsubstituted C.sub.2-C.sub.50 heteroaryl, substituted or unsubstituted C.sub.6-C.sub.50 fused polycyclic non-aromatic hydrocarbon rings, substituted or unsubstituted C.sub.2-C.sub.50 fused polycyclic non-aromatic heterocyclic rings, 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.5-C.sub.30 arylthioxy, substituted or unsubstituted amine, substituted or unsubstituted silyl, nitro, cyano, and halogen, R.sub.11 is selected from 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 cycloalkenyl, substituted or unsubstituted C.sub.1-C.sub.30 heterocycloalkyl, substituted or unsubstituted C.sub.2-C.sub.50 heteroaryl, substituted or unsubstituted C.sub.6-C.sub.50 fused polycyclic non-aromatic hydrocarbon rings, and substituted or unsubstituted C.sub.2-C.sub.50 fused polycyclic non-aromatic heterocyclic rings, provided that when the adjacent Z is CR, each of R.sub.15, R.sub.16, and R.sub.1 to R.sub.5 optionally forms an alicyclic or aromatic monocyclic or polycyclic ring with R, with the proviso that R.sub.2 and R.sub.3 together optionally form an alicyclic or aromatic monocyclic or polycyclic ring and R.sub.4 and R.sub.5 together optionally form an alicyclic or aromatic monocyclic or polycyclic ring, with the proviso that at least one of Y.sub.2 and Y.sub.3 is represented by Structure A: ##STR00324## wherein R.sub.6 is selected from substituted or unsubstituted C.sub.1-C.sub.30 alkyl, substituted or unsubstituted C.sub.6-C.sub.20 aryl, substituted or unsubstituted C.sub.2-C.sub.20 heteroaryl, substituted or unsubstituted C.sub.6-C.sub.50 fused polycyclic non-aromatic hydrocarbon rings, and substituted or unsubstituted C.sub.2-C.sub.50 fused polycyclic non-aromatic heterocyclic rings, R.sub.7 is selected from hydrogen, deuterium, substituted or unsubstituted C.sub.1-C.sub.30 alkyl, substituted or unsubstituted C.sub.3-C.sub.30 cycloalkyl, substituted or unsubstituted C.sub.6-C.sub.50 aryl, and substituted or unsubstituted C.sub.2-C.sub.20 heteroaryl, and R.sub.8 to R.sub.10 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.2-C.sub.30 alkynyl, substituted or unsubstituted C.sub.2-C.sub.30 alkenyl, 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 cycloalkenyl, substituted or unsubstituted C.sub.1-C.sub.30 heterocycloalkyl, substituted or unsubstituted C.sub.2-C.sub.50 heteroaryl, substituted or unsubstituted C.sub.6-C.sub.50 fused polycyclic non-aromatic hydrocarbon rings, substituted or unsubstituted C.sub.2-C.sub.50 fused polycyclic non-aromatic heterocyclic rings, 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.5-C.sub.30 arylthioxy, substituted or unsubstituted amine, substituted or unsubstituted silyl, nitro, cyano, and halogen, with the proviso that each of R.sub.6 to R.sub.10 optionally forms an alicyclic or aromatic monocyclic or polycyclic ring with an adjacent substituent.

2. The compound according to claim 1, wherein the compound represented by Formula A-1 is selected from the following compounds 1 to 87: ##STR00325## ##STR00326## ##STR00327## ##STR00328## ##STR00329## ##STR00330## ##STR00331## ##STR00332## ##STR00333## ##STR00334## ##STR00335## ##STR00336## ##STR00337## ##STR00338## ##STR00339## ##STR00340## ##STR00341## ##STR00342## ##STR00343## ##STR00344## ##STR00345## ##STR00346##

3. 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 is a light emitting layer composed of a host and a dopant and wherein the dopant is the compound represented by Formula A-1 according to claim 1.

4. 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 is a light emitting layer comprising a host and a dopant and wherein the dopant comprises at least one compound represented by Formula A-1: ##STR00347## wherein each Z is independently CR or N, R and R.sub.12 to R.sub.16 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.2-C.sub.30 alkenyl, substituted or unsubstituted C.sub.2-C.sub.30 alkynyl, 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 cycloalkenyl, substituted or unsubstituted C.sub.1-C.sub.30 heterocycloalkyl, substituted or unsubstituted C.sub.2-C.sub.50 heteroaryl, substituted or unsubstituted C.sub.6-C.sub.50 fused polycyclic non-aromatic hydrocarbon rings, substituted or unsubstituted C.sub.2-C.sub.50 fused polycyclic non-aromatic heterocyclic rings, 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.5-C.sub.30 arylthioxy, substituted or unsubstituted amine, substituted or unsubstituted silyl, substituted or unsubstituted germanium, substituted or unsubstituted boron, substituted or unsubstituted aluminum, phosphoryl, hydroxyl, selenium, tellurium, nitro, cyano, and halogen, with the proviso that each of R.sub.12 to R.sub.16 optionally forms an aliphatic or aromatic monocyclic or polycyclic ring with the other adjacent group(s), the moieties Z are identical to or different from each other, the groups R are identical to or different from each other, with the proviso that the groups R are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, Y.sub.1 is O or S, Y.sub.2 and Y.sub.3 are identical to or different from each other and are each independently selected from N—R.sub.1, CR.sub.2R.sub.3, O, S, Se, and SiR.sub.4R.sub.5, R.sub.1 to R.sub.5 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.2-C.sub.30 alkynyl, substituted or unsubstituted C.sub.2-C.sub.30 alkenyl, 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 cycloalkenyl, substituted or unsubstituted C.sub.1-C.sub.30 heterocycloalkyl, substituted or unsubstituted C.sub.2-C.sub.50 heteroaryl, substituted or unsubstituted C.sub.6-C.sub.50 fused polycyclic non-aromatic hydrocarbon rings, substituted or unsubstituted C.sub.2-C.sub.50 fused polycyclic non-aromatic heterocyclic rings, 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.5-C.sub.30 arylthioxy, substituted or unsubstituted amine, substituted or unsubstituted silyl, nitro, cyano, and halogen, R.sub.11 is selected from 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 cycloalkenyl, substituted or unsubstituted C.sub.1-C.sub.30 heterocycloalkyl, substituted or unsubstituted C.sub.2-C.sub.50 heteroaryl, substituted or unsubstituted C.sub.6-C.sub.50 fused polycyclic non-aromatic hydrocarbon rings, and substituted or unsubstituted C.sub.2-C.sub.50 fused polycyclic non-aromatic heterocyclic rings, provided that when the adjacent Z is CR, each of R.sub.15, R.sub.16, and R.sub.1 to R.sub.5 optionally forms an alicyclic or aromatic monocyclic or polycyclic ring with R, with the proviso that R.sub.2 and R.sub.3 together optionally form an alicyclic or aromatic monocyclic or polycyclic ring and R.sub.4 and R.sub.5 together optionally form an alicyclic or aromatic monocyclic or polycyclic ring, with the proviso that at least one of Y.sub.2 and Y.sub.3 is represented by Structure A: ##STR00348## wherein R.sub.6 is selected from substituted or unsubstituted C.sub.1-C.sub.30 alkyl, substituted or unsubstituted C.sub.6-C.sub.20 aryl, substituted or unsubstituted C.sub.2-C.sub.20 heteroaryl, substituted or unsubstituted C.sub.6-C.sub.50 fused polycyclic non-aromatic hydrocarbon rings, and substituted or unsubstituted C.sub.2-C.sub.50 fused polycyclic non-aromatic heterocyclic rings, R.sub.7 is selected from hydrogen, deuterium, substituted or unsubstituted C.sub.1-C.sub.30 alkyl, substituted or unsubstituted C.sub.3-C.sub.30 cycloalkyl, substituted or unsubstituted C.sub.6-C.sub.50 aryl, and substituted or unsubstituted C.sub.2-C.sub.20 heteroaryl, and R.sub.8 to R.sub.10 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.2-C.sub.30 alkynyl, substituted or unsubstituted C.sub.2-C.sub.30 alkenyl, 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 cycloalkenyl, substituted or unsubstituted C.sub.1-C.sub.30 heterocycloalkyl, substituted or unsubstituted C.sub.2-C.sub.50 heteroaryl, substituted or unsubstituted C.sub.6-C.sub.50 fused polycyclic non-aromatic hydrocarbon rings, substituted or unsubstituted C.sub.2-C.sub.50 fused polycyclic non-aromatic heterocyclic rings, 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.5-C.sub.30 arylthioxy, substituted or unsubstituted amine, substituted or unsubstituted silyl, nitro, cyano, and halogen, with the proviso that each of R.sub.6 to R.sub.10 optionally forms an alicyclic or aromatic monocyclic or polycyclic ring with an adjacent substituent; and the host is an anthracene compound represented by Formula 1: ##STR00349## wherein R.sub.21 to R.sub.28 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.2-C.sub.30 alkynyl, substituted or unsubstituted C.sub.2-C.sub.30 alkenyl, 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.5-C.sub.30 arylthioxy, substituted or unsubstituted amine, substituted or unsubstituted silyl, substituted or unsubstituted C.sub.3-C.sub.30 mixed aliphatic-aromatic cyclic groups, nitro, cyano, and halogen, Ar.sub.1 and Ar.sub.3 are identical to or different from each other and are each independently substituted or unsubstituted C.sub.6-C.sub.30 arylene or substituted or unsubstituted C.sub.5-C.sub.30 heteroarylene, Ar.sub.2 and Ar.sub.4 are identical to or different from each other and are each independently selected from 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, and substituted or unsubstituted C.sub.3-C.sub.30 mixed aliphatic-aromatic cyclic groups, D.sub.n represents the number of deuterium (D) atoms replacing hydrogen atoms in Ar.sub.1 to Ar.sub.4, and n is an integer from 0 to 40.

5. The organic electroluminescent device according to claim 4, wherein at least one of R.sub.21 to R.sub.28 in Formula 1 is a deuterium atom.

6. The organic electroluminescent device according to claim 4, wherein the compound represented by Formula 1 is selected from the group consisting of the following compounds 1-1: ##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## ##STR00414## ##STR00415## ##STR00416## ##STR00417## ##STR00418## ##STR00419## ##STR00420## ##STR00421## ##STR00422## ##STR00423## ##STR00424## ##STR00425## ##STR00426## ##STR00427## ##STR00428## ##STR00429## ##STR00430## ##STR00431## ##STR00432## ##STR00433## ##STR00434##

7. The organic electroluminescent device according to claim 4, wherein the compound represented by Formula 1 is selected from the group consisting of the following compounds 1-2: ##STR00435## ##STR00436## ##STR00437## ##STR00438## ##STR00439## ##STR00440## ##STR00441## ##STR00442## ##STR00443## ##STR00444## ##STR00445## ##STR00446## ##STR00447## ##STR00448## ##STR00449## ##STR00450## ##STR00451## ##STR00452## ##STR00453## ##STR00454## ##STR00455## ##STR00456## ##STR00457## ##STR00458## ##STR00459## ##STR00460## ##STR00461## ##STR00462## ##STR00463## ##STR00464## ##STR00465## ##STR00466## ##STR00467## ##STR00468## ##STR00469## ##STR00470## ##STR00471## ##STR00472## ##STR00473## ##STR00474## ##STR00475## ##STR00476## ##STR00477## ##STR00478## ##STR00479## ##STR00480## ##STR00481## ##STR00482## ##STR00483## ##STR00484## ##STR00485## ##STR00486## ##STR00487## ##STR00488## ##STR00489## ##STR00490## ##STR00491## ##STR00492## ##STR00493## ##STR00494## ##STR00495## ##STR00496## ##STR00497## ##STR00498## ##STR00499## ##STR00500## ##STR00501## ##STR00502## ##STR00503## ##STR00504## ##STR00505## ##STR00506## ##STR00507## ##STR00508## ##STR00509## ##STR00510## ##STR00511## ##STR00512## ##STR00513## ##STR00514## ##STR00515## ##STR00516## ##STR00517## ##STR00518## ##STR00519## ##STR00520## ##STR00521## ##STR00522## ##STR00523## ##STR00524## ##STR00525## ##STR00526## ##STR00527## ##STR00528## ##STR00529## ##STR00530## ##STR00531## ##STR00532## ##STR00533## ##STR00534## ##STR00535## ##STR00536## ##STR00537## ##STR00538## ##STR00539##

8. The organic electroluminescent device according to claim 3, wherein each of the organic layers is formed by a deposition or solution process.

9. The organic electroluminescent device according to claim 3, wherein one or more dopants other than the compound represented by Formula A-1 are mixed or stacked in the light emitting layer.

10. The organic electroluminescent device according to claim 4, wherein one or more hosts other than the compound represented by Formula 1 are mixed or stacked in the light emitting layer.

11. The organic electroluminescent device according to claim 3, 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 9

SYNTHESIS EXAMPLE 1-1: SYNTHESIS OF A-1

[0092] ##STR00271##

[0093] 30 g of A-1a, 16.1 g of A-1b, 1.79 g of tris(dibenzylideneacetone)dipalladium(0), 1.22 g of bis(diphenylphosphino)-1,1′-binaphthyl, 18.8 g of sodium tert-butoxide, and 400 mL of toluene were placed in a reactor. The mixture was stirred under reflux for 3 h. The reaction mixture was cooled to room temperature and ethyl acetate and water were added thereto. The organic layer was separated and purified by silica gel chromatography to afford A-1 (29.2 g, 73.1%).

SYNTHESIS EXAMPLE 1-2: SYNTHESIS OF A-2

[0094] ##STR00272##

[0095] 20 g of A-1, 14.5 g of A-2a, 0.5 g of bis(tri-tert-butylphosphine)palladium(0), 7 g of sodium tert-butoxide, and 300 mL of toluene were placed in a reactor. The mixture was stirred under reflux for 6 h. The reaction mixture was cooled to room temperature and ethyl acetate and water were added thereto. The organic layer was separated and purified by silica gel chromatography to afford A-2 (18.5 g, 63.4%).

SYNTHESIS EXAMPLE 1-3: SYNTHESIS OF A-3

[0096] ##STR00273##

[0097] A-3 (yield 85.1%) was synthesized in the same manner as in Synthesis Example 1-1, except that A-3a and A-3b were used instead of A-1a and A-1b, respectively.

SYNTHESIS EXAMPLE 1-4: SYNTHESIS OF A-4

[0098] ##STR00274##

[0099] 50 g of A-3, 56.3 g of A-4a, 0.4 g of palladium(II) acetate, 23.9 g of sodium tert-butoxide, 1 g of Xantphos, and 500 mL of toluene were placed in a reactor. The mixture was stirred under reflux for 16 h. The reaction mixture was cooled to room temperature and ethyl acetate and water were added thereto. The organic layer was separated and purified by silica gel chromatography to afford A-4 (35 g, 46.2%).

SYNTHESIS EXAMPLE 1-5: SYNTHESIS OF A-5

[0100] ##STR00275##

[0101] A-5 (yield 82.3%) was synthesized in the same manner as in Synthesis Example 1-1, except that A-4 and A-5a were used instead of A-1a and A-1b, respectively.

SYNTHESIS EXAMPLE 1-6: SYNTHESIS OF A-6

[0102] ##STR00276##

[0103] A-6 (yield 93%) was synthesized in the same manner as in Synthesis Example 1-2, except that A-5 and A-2 were used instead of A-1 and A-2a, respectively.

SYNTHESIS EXAMPLE 1-7: SYNTHESIS OF 9

[0104] ##STR00277##

[0105] 40 g of A-6 and 480 mL of tert-butylbenzene were placed in a reactor and 60 mL of a 1.7 M tert-butyllithium pentane solution was added dropwise thereto at −78° C. The mixture was heated to 60° C., followed by stirring for 2 h. Then, nitrogen at 60° C. was blown into the mixture to completely remove pentane. After cooling to −78° C., 7 mL of boron tribromide was added dropwise. The resulting mixture was allowed to warm to room temperature, followed by stirring for 2 h. After cooling to 0° C., 12 mL of N,N-diisopropylethylamine was added dropwise. The mixture was heated to 120° C., followed by stirring for 16 h. The reaction mixture was cooled to room temperature and a 10% aqueous solution of sodium acetate and ethyl acetate were added thereto. The organic layer was separated, concentrated under reduced pressure, and purified by silica gel chromatography to afford 9 (5 g, 12.8%).

[0106] MS (MALDI-TOF): m/z 1154.52 [M.sup.+]

SYNTHESIS EXAMPLE 2: SYNTHESIS OF 10

SYNTHESIS EXAMPLE 2-1: SYNTHESIS OF B-1

[0107] ##STR00278##

[0108] B-1 (yield 74.8%) was synthesized in the same manner as in Synthesis Example 1-1, except that B-1a and A-3b were used instead of A-1a and A-1b, respectively.

SYNTHESIS EXAMPLE 2-2: SYNTHESIS OF B-2

[0109] ##STR00279##

[0110] B-2 (yield 88.7%) was synthesized in the same manner as in Synthesis Example 1-2, except that B-1 was used instead of A-1.

SYNTHESIS EXAMPLE 2-3: SYNTHESIS OF B-3

[0111] ##STR00280##

[0112] B-3 (yield 89.4%) was synthesized in the same manner as in Synthesis Example 1-5, except that B-3a was used instead of A-5a.

SYNTHESIS EXAMPLE 2-4: SYNTHESIS OF B-4

[0113] ##STR00281##

[0114] B-4 (yield 94.2%) was synthesized in the same manner as in Synthesis Example 1-6, except that B-2 and B-3 were used instead of A-2 and A-5, respectively.

SYNTHESIS EXAMPLE 2-5: SYNTHESIS OF 10

[0115] ##STR00282##

[0116] 10 (yield 11.4%) was synthesized in the same manner as in Synthesis Example 1-7, except that B-4 was used instead of A-6.

[0117] MS (MALDI-TOF): m/z 1095.57 [M.sup.+]

SYNTHESIS EXAMPLE 3: SYNTHESIS OF 13

[0118] 13 (yield 12.5%) was synthesized in the same manner as in Synthesis Example 2, except that (1,1′-biphenyl)-4-amine was used instead of A-3b in Synthesis Example 2-1.

[0119] MS (MALDI-TOF): m/z 1115.54 [M.sup.+]

SYNTHESIS EXAMPLE 4: SYNTHESIS OF 14

SYNTHESIS EXAMPLE 4-1: SYNTHESIS OF C-1

[0120] ##STR00283##

[0121] C-1 (yield 72.1%) was synthesized in the same manner as in Synthesis Example 2-1, except that C-1a was used instead of B-1a.

SYNTHESIS EXAMPLE 4-2: SYNTHESIS OF C-2

[0122] ##STR00284##

[0123] C-2 (yield 95.3%) was synthesized in the same manner as in Synthesis Example 1-2, except that C-1 and C-2a were used instead of A-1 and A-2a, respectively.

SYNTHESIS EXAMPLE 4-3: SYNTHESIS OF C-3

[0124] ##STR00285##

[0125] C-3 (yield 93.7%) was synthesized in the same manner as in Synthesis Example 2-4, except that C-2 was used instead of B-2.

SYNTHESIS EXAMPLE 4-4: SYNTHESIS OF 14

[0126] ##STR00286##

[0127] 14 (yield 11.4%) was synthesized in the same manner as in Synthesis Example 1-7, except that C-3 was used instead of A-6.

[0128] MS (MALDI-TOF): m/z 1039.51 [M.sup.+]

SYNTHESIS EXAMPLE 5: SYNTHESIS OF 18

SYNTHESIS EXAMPLE 5-1: SYNTHESIS OF D-1

[0129] ##STR00287##

[0130] D-1 (yield 72.8%) was synthesized in the same manner as in Synthesis Example 1-1, except that D-1a was used instead of A-1b.

SYNTHESIS EXAMPLE 5-2: SYNTHESIS OF D-2

[0131] ##STR00288##

[0132] D-2 (yield 93.1%) was synthesized in the same manner as in Synthesis Example 4-2, except that D-1 was used instead of C-1.

SYNTHESIS EXAMPLE 5-3: SYNTHESIS OF D-3

[0133] ##STR00289##

[0134] D-3 (yield 93.7%) was synthesized in the same manner as in Synthesis Example 2-4, except that D-2 was used instead of B-2.

SYNTHESIS EXAMPLE 5-4: SYNTHESIS OF 18

[0135] ##STR00290##

[0136] 18 (yield 11.4%) was synthesized in the same manner as in Synthesis Example 1-7, except that D-3 was used instead of A-6.

[0137] MS (MALDI-TOF): m/z 1154.52 [M.sup.+]

SYNTHESIS EXAMPLE 6: SYNTHESIS OF 31

SYNTHESIS EXAMPLE 6-1: SYNTHESIS OF E-1

[0138] ##STR00291##

[0139] E-1 (yield 95.1%) was synthesized in the same manner as in Synthesis Example 2-2, except that C-2a was used instead of A-2a.

SYNTHESIS EXAMPLE 6-2: SYNTHESIS OF E-2

[0140] ##STR00292##

[0141] 60 g of E-2a, 66.9 g of E-2b, 15.2 g of tetrakis(triphenylphosphine)palladium, 109.1 g of potassium carbonate, 300 mL of toluene, 180 mL of ethanol, and 180 mL of water were placed in a reactor. The mixture was stirred under reflux for 16 h. The reaction mixture was cooled to room temperature and ethyl acetate and water were added thereto. The organic layer was separated and purified by silica gel chromatography to afford E-2 (44.5 g, 75%).

SYNTHESIS EXAMPLE 6-3: SYNTHESIS OF E-3

[0142] ##STR00293##

[0143] E-3 (yield 79.2%) was synthesized in the same manner as in Synthesis Example 1-5, except that E-2 was used instead of A-5a.

SYNTHESIS EXAMPLE 6-4: SYNTHESIS OF E-4

[0144] ##STR00294##

[0145] E-4 (yield 91.6%) was synthesized in the same manner as in Synthesis Example 1-6, except that E-1 and E-3 were used instead of A-2 and A-5, respectively.

SYNTHESIS EXAMPLE 6-5: SYNTHESIS OF 31

[0146] ##STR00295##

[0147] 31 (yield 11.4%) was synthesized in the same manner as in Synthesis Example 1-7, except that E-4 was used instead of A-6.

[0148] MS (MALDI-TOF): m/z 1205.55 [M.sup.+]

SYNTHESIS EXAMPLE 7: SYNTHESIS OF 36

SYNTHESIS EXAMPLE 7-1: SYNTHESIS OF F-1

[0149] ##STR00296##

[0150] F-1 (yield 81%) was synthesized in the same manner as in Synthesis Example 6-2, except that F-1a and F-1b were used instead of E-2a and E-2b, respectively.

SYNTHESIS EXAMPLE 7-2: SYNTHESIS OF F-2

[0151] ##STR00297##

[0152] 53.1 g of F-1 and 424 mL of tetrahydrofuran were placed in a reactor and 116 mL of a 2.0 M lithium diisopropylamide solution was added dropwise thereto at −78° C. After stirring at −78° C. for 2 h, hexachloroethane was slowly added. The mixture was allowed to warm to room temperature, followed by stirring. To the reaction mixture were added ethyl acetate and water. The organic layer was separated and purified by silica gel chromatography to afford F-2 (19 g, 32%).

SYNTHESIS EXAMPLE 7-3: SYNTHESIS OF F-3

[0153] ##STR00298##

[0154] F-3 (yield 72.5%) was synthesized in the same manner as in Synthesis Example 2-1, except that F-2 was used instead of B-1a.

SYNTHESIS EXAMPLE 7-4: SYNTHESIS OF F-4

[0155] ##STR00299##

[0156] F-4 (yield 73.7%) was synthesized in the same manner as in Synthesis Example 1-2, except that F-3 was used instead of A-1.

SYNTHESIS EXAMPLE 7-5: SYNTHESIS OF F-5

[0157] ##STR00300##

[0158] F-5 (yield 93.3%) was synthesized in the same manner as in Synthesis Example 1-6, except that F-4 and B-3 were used instead of A-2 and A-5, respectively.

SYNTHESIS EXAMPLE 7-6: SYNTHESIS OF 36

[0159] ##STR00301##

[0160] 36 (yield 12.1%) was synthesized in the same manner as in Synthesis Example 1-7, except that F-5 was used instead of A-6.

[0161] MS (MALDI-TOF): m/z 1171.60 [M.sup.+]

SYNTHESIS EXAMPLE 8: SYNTHESIS OF 61

SYNTHESIS EXAMPLE 8-1: SYNTHESIS OF G-1

[0162] ##STR00302##

[0163] G-1 (yield 72.7%) was synthesized in the same manner as in Synthesis Example 1-1, except that C-1a was used instead of A-1a.

SYNTHESIS EXAMPLE 8-2: SYNTHESIS OF G-2

[0164] ##STR00303##

[0165] G-2 (yield 65.8%) was synthesized in the same manner as in Synthesis Example 1-2, except that G-1 was used instead of A-1.

SYNTHESIS EXAMPLE 8-3: SYNTHESIS OF G-3

[0166] ##STR00304##

[0167] G-3 (yield 92.8%) was synthesized in the same manner as in Synthesis Example 2-4, except that G-2 was used instead of B-2.

SYNTHESIS EXAMPLE 8-4: SYNTHESIS OF 61

[0168] ##STR00305##

[0169] 61 (yield 12.2%) was synthesized in the same manner as in Synthesis Example 1-7, except that G-3 was used instead of A-6.

[0170] MS (MALDI-TOF): m/z 1053.49 [M.sup.+]

SYNTHESIS EXAMPLE 9: SYNTHESIS OF 70

SYNTHESIS EXAMPLE 9-1: SYNTHESIS OF H-1

[0171] ##STR00306##

[0172] H-1 (yield 86.4%) was synthesized in the same manner as in Synthesis Example 1-2, except that C-1 was used instead of A-1.

SYNTHESIS EXAMPLE 9-2: SYNTHESIS OF H-2

[0173] ##STR00307##

[0174] H-2 (yield 84.7%) was synthesized in the same manner as in Synthesis Example 1-3, except that H-2a was used instead of A-3a.

SYNTHESIS EXAMPLE 9-3: SYNTHESIS OF H-3

[0175] ##STR00308##

[0176] H-3 (yield 47.3%) was synthesized in the same manner as in Synthesis Example 1-4, except that H-2 was used instead of A-3.

SYNTHESIS EXAMPLE 9-4: SYNTHESIS OF H-4

[0177] ##STR00309##

[0178] H-4 (yield 88.2%) was synthesized in the same manner as in Synthesis Example 2-3, except that H-3 was used instead of A-4.

SYNTHESIS EXAMPLE 9-5: SYNTHESIS OF H-5

[0179] ##STR00310##

[0180] H-5 (yield 92.3%) was synthesized in the same manner as in Synthesis Example 1-6, except that H-1 and H-4 were used instead of A-2 and A-5, respectively.

SYNTHESIS EXAMPLE 9-6: SYNTHESIS OF 70

[0181] ##STR00311##

[0182] 70 (yield 12.1%) was synthesized in the same manner as in Synthesis Example 1-7, except that H-5 was used instead of A-6.

[0183] MS (MALDI-TOF): m/z 1075.60 [M.sup.+]

EXAMPLES 1-9: FABRICATION OF ORGANIC ELECTROLUMINESCENT DEVICES

[0184] 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. The compound represented by Acceptor-1 as an electron acceptor and the compound represented by Formula F were deposited in a ratio of 2:98 on the ITO to form a 100 Å thick hole injecting layer. The compound represented by Formula F was used to form a 550 Å thick hole transport layer. Subsequently, the compound represented by Formula G was used to form a 50 Å thick electron blocking layer. A mixture of the host represented by BH-1 and the inventive compound (2 wt %) shown in Table 1 was used to form a 200 Å thick light emitting layer. Thereafter, the compound represented by Formula H was used to form a 50 Å hole blocking layer on the light emitting layer. A mixture of the compound represented by Formula E-1 and the compound represented by Formula E-2 in a ratio of 1:1 was used to form a 250 Å thick electron transport layer on the hole blocking layer. The compound represented by Formula E-2 was used to form a 10 Å thick electron injection layer on the electron transport layer. Al was used to form a 1000 Å thick Al electrode on the electron injection layer, completing the fabrication of an organic electroluminescent device. The luminescent properties of the organic electroluminescent device were measured at 0.4 mA.

##STR00312## ##STR00313##

COMPARATIVE EXAMPLES 1-5

[0185] Organic electroluminescent devices were fabricated in the same manner as in Examples 1-9, except that BD1, BD2, BD3, BD4 or BD5 was used as a dopant instead of the inventive compound. The luminescent properties of the organic electroluminescent devices were measured at 0.4 mA. The structures of BD1 to BD5 are as follow:

##STR00314## ##STR00315##

[0186] The organic electroluminescent devices of Examples 1-9 and Comparative Examples 1-5 were measured for voltage, external quantum efficiency, and lifetime. The results are shown in Table 1.

TABLE-US-00001 TABLE 1 Voltage Efficiency Lifetime Example No. Host Dopant (V) (EQE, %) (T97, hr) Example 1 BH-1 9 3.4 10.83 240 Example 2 BH-1 10 3.4 11.71 250 Example 3 BH-1 13 3.4 10.71 235 Example 4 BH-1 14 3.4 11.53 290 Example 5 BH-1 18 3.4 10.58 273 Example 6 BH-1 31 3.4 10.64 221 Example 7 BH-1 36 3.4 10.38 237 Example 8 BH-1 61 3.4 10.66 240 Example 9 BH-1 70 3.4 10.91 261 Comparative BH-1 BD-1 3.4 9.62 190 Example 1 Comparative BH-1 BD-2 3.4 9.96 165 Example 2 Comparative BH-1 BD-3 3.4 9.75 158 Example 3 Comparative BH-1 BD-4 3.4 8.74 87 Example 4 Comparative BH-1 BD-5 3.4 8.22 85 Example 5

[0187] As can be seen from the results in Table 1, the organic electroluminescent devices of Examples 1-9, each of which employed the inventive compound as a dopant, showed significantly improved life characteristics and high external quantum efficiencies compared to the devices of Comparative Examples 1-5, each of which employed a compound whose structural features were contrasted with those of the inventive compound. These results concluded that the use of the inventive compounds makes the organic electroluminescent devices highly efficient and long lasting.

EXPERIMENTAL EXAMPLE 1: MEASUREMENT OF EL MAXIMUM PEAK WAVELENGTHS AND SUBLIMATION TEMPERATURES

[0188] The EL maximum peak wavelengths and sublimation temperatures of 9, 10, and 13 were measured under the same conditions.

##STR00316## ##STR00317## ##STR00318##

TABLE-US-00002 TABLE 2 9 10 13 BD-1 BD-2 BD-3 EL λ.sub.max (nm) 459 459 460 461 462 463 Sub. T (° C.) 340 345 355 375 370 375

[0189] The inventive compounds 9, 10, and 13 represented by Formula A-1 are different from BD-1, BD-2, and BD-3 in that the phenyl derivative is substituted ortho to at least one of the aryl groups bonded to the amine atom in the structure of the diarylamine moiety of each of the compounds 9, 10, and 13. Due to this difference, the sublimation temperatures of the inventive compounds were reduced by 20-30° C. compared to those of the comparative compounds, as shown in Table 2. As a result, the inventive compounds can be prevented from thermal decomposition during high-temperature sublimation for purification and can improve the lifetimes of the electroluminescent devices without significant degradation during long-term driving.

[0190] In addition, the EL maximum peaks of the inventive compounds were shifted to shorter wavelengths (blue shifted) compared to those of the comparative compounds. As a result, the use of the inventive compounds as dopants in the light emitting layers of the organic electroluminescent devices can achieve blue light emission with improved color purity.

EXAMPLES 10-13: FABRICATION OF ORGANIC ELECTROLUMINESCENT DEVICES

[0191] 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. The compound represented by Acceptor-1 as an electron acceptor and the compound represented by Formula F were deposited in a ratio of 2:98 on the ITO to form a 100 Å thick hole injecting layer. The compound represented by Formula F was used to form a 550 Å thick hole transport layer. Subsequently, the compound represented by Formula G was used to form a 50 Å thick electron blocking layer. A mixture of the host represented by BH-2 and the inventive compound (2 wt %) shown in Table 1 was used to form a 200 Å thick light emitting layer. Thereafter, the compound represented by Formula H was used to form a 50 Å hole blocking layer on the light emitting layer. A mixture of the compound represented by Formula E-1 and the compound represented by Formula E-2 in a ratio of 1:1 was used to form a 250 Å thick electron transport layer on the hole blocking layer. The compound represented by Formula E-2 was used to form a 10 Å thick electron injection layer on the electron transport layer. Al was used to form a 1000 Å thick Al electrode on the electron injection layer, completing the fabrication of an organic electroluminescent device. The luminescent properties of the organic electroluminescent device were measured at 0.4 mA.

##STR00319## ##STR00320##

COMPARATIVE EXAMPLES 6-9

[0192] Organic electroluminescent devices were fabricated in the same manner as in Examples 10-13, except that BH-1 was used as a host compound to form a light emitting layer instead of BH-2. The luminescent properties of the organic electroluminescent devices were measured at 0.4 mA.

TABLE-US-00003 TABLE 3 Voltage Efficiency Lifetime Example No. Host Dopant (V) (EQE, %) (T97, hr) Example 10 BH-2 9 3.4 11.28 387 Example 11 BH-2 14 3.4 11.84 452 Example 12 BH-2 31 3.4 10.97 365 Example 13 BH-2 70 3.4 11.21 412 Comparative BH-1 9 3.4 10.83 240 Example 6 Comparative BH-1 14 3.4 11.53 290 Example 7 Comparative BH-1 31 3.4 10.64 221 Example 8 Comparative BH-1 70 3.4 10.97 261 Example 9

[0193] The results in Table 3 compare data obtained from the organic electroluminescent devices of Examples 10-13 with those from the organic electroluminescent devices of Comparative Examples 6-9. The organic electroluminescent devices, each of which employed the inventive compound as a dopant and BH-2 as a host, showed significantly improved efficiencies and life characteristics compared to the devices employing BH-1, whose structure was contrasted with that of BH-2, as a host.

EXAMPLES 14-17: FABRICATION OF ORGANIC ELECTROLUMINESCENT DEVICES

[0194] Organic electroluminescent devices were fabricated in the same manner as in Examples 10-13, except that BH-3 was used as a host compound to form a light emitting layer instead of BH-2. The luminescent properties of the organic electroluminescent devices were measured at 0.4 mA. The structure of BH-3 is as follows:

##STR00321##

COMPARATIVE EXAMPLES 10-13

[0195] Organic electroluminescent devices were fabricated in the same manner as in Examples 14-17, except that BH-4 was used as a host compound to form a light emitting layer instead of BH-3. The luminescent properties of the organic electroluminescent devices were measured at 0.4 mA. The structure of BH-4 is as follows:

##STR00322##

TABLE-US-00004 TABLE 4 Voltage Efficiency Lifetime Example No. Host Dopant (V) (EQE, %) (T97, hr) Example 14 BH-3 9 3.9 11.61 264 Example 15 BH-3 14 3.9 12.22 305 Example 16 BH-3 31 3.9 11.42 267 Example 17 BH-3 70 3.9 11.74 302 Comparative BH-4 9 3.9 11.48 241 Example 10 Comparative BH-4 14 3.9 12.17 286 Example 11 Comparative BH-4 31 3.9 11.28 237 Example 12 Comparative BH-4 70 3.9 11.63 259 Example 13

[0196] The results in Table 4 compare data obtained from the organic electroluminescent devices of Examples 14-17 with those from the organic electroluminescent devices of Comparative Examples 10-13. The organic electroluminescent devices, each of which employed the inventive compound as a dopant and BH-3 as a host, showed significantly improved life characteristics compared to the devices employing BH-4, whose structure was contrasted with that of BH-3, as a host. The efficiencies of the organic electroluminescent devices of Examples 14-17 were at a level comparable to those of the organic electroluminescent devices of Comparative Examples 10-13.