Organic electroluminescent compound and organic electroluminescent device comprising the same

Abstract

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound of the present disclosure, it is possible to provide an organic electroluminescent device having low driving voltage and/or improved lifespan properties.

Claims

1. An organic electroluminescent compound represented by the following formula 1: ##STR00181## wherein X.sub.1 represents NR.sub.11; R.sub.11 and R.sub.12, each independently, are represented by -L-Ar; R.sub.1 to R.sub.3, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be linked to an adjacent substituent to form a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic ring; Ar represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl wherein the (3- to 30-membered)heteroaryl group is selected from the group consisting of furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl and dihydroacridinyl; L represents a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene; and a represents an integer of 1 to 6, b and c, each independently, represent an integer of 1 to 4, where if a to c, each independently, are an integer of 2 or more, each of R.sub.1 to R.sub.3 may be the same or different.

2. The organic electroluminescent compound according to claim 1, wherein the substituents of the substituted (C1-C30)alkyl(ene), the substituted (C6-C30)aryl(ene), the substituted (3- to 30-membered)heteroaryl(ene), the substituted (C3-C30)cycloalkyl(ene), the substituted (C1-C30)alkoxy, the substituted tri(C1-C30)alkylsilyl, the substituted di(C1-C30)alkyl(C6-C30)arylsilyl, the substituted (C1-C30)alkyldi(C6-C30)arylsilyl, the substituted tri(C6-C30)arylsilyl, the substituted mono- or di-(C1-C30)alkylamino, the substituted mono- or di-(C6-C30)arylamino, the substituted (C1-C30)alkyl(C6-C30)arylamino, and the substituted (3- to 30-membered) mono- or polycyclic ring in L, Ar, R.sub.1 to R.sub.3, 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 (5- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl; a (C6-C30)aryl unsubstituted or substituted with a (5- to 30-membered)heteroaryl; 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 unsubstituted or substituted with a (C1-C30)alkyl; 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 organic electroluminescent compound according to claim 1, wherein formula 1 is represented by the following formula 2: ##STR00182## wherein R.sub.11 and R.sub.12, each independently, are represented by -L-Ar; L represents a single bond, an unsubstituted (C6-C25)arylene, or an unsubstituted (5- to 25-membered)heteroarylene; Ar represents a (C6-C25)aryl unsubstituted or substituted with a (C1-C10)alkyl or a cyano, or a (5- to 25-membered)heteroaryl unsubstituted or substituted with a (C6-C25)aryl wherein the (5- to 25-membered)heteroaryl group is selected from the group consisting of furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl and dihydroacridinyl; R.sub.1 to R.sub.3, each independently, represent an unsubstituted (C6-C25)aryl; and a, b, and c, each independently, represent 0 or 1.

4. The organic electroluminescent compound according to claim 1, wherein formula 1 is represented by any one of the following formulas 4 to 6: ##STR00183## wherein X.sub.1, R.sub.11, and R.sub.12 are as defined in claim 1; L represents a single bond, an unsubstituted (C6-C18)arylene, or an unsubstituted (5- to 20-membered)heteroarylene; Ar represents a (C6-C18)aryl unsubstituted or substituted with a (C1-C6)alkyl or a cyano, or a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C6-C18)aryl wherein the (5- to 20-membered)heteroaryl group is selected from the group consisting of furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl and dihydroacridinyl; R.sub.1 to R.sub.3, each independently, represent an unsubstituted (C6-C18)aryl; and a, b, and c, each independently, represent 0 or 1.

5. The organic electroluminescent compound according to claim 1, wherein formula 1 is represented by any one of the following formulas 7 to 11: ##STR00184## wherein, R.sub.11 and R.sub.12 are as defined in claim 1.

6. The organic electroluminescent compound according to claim 5, wherein the compound represented by formula 1 is any one selected from the following compounds C1-1 to C1-96, C2-1 to C2-54, C2-56 to C2-58, C2-60 to C2-62, C2-64 to C2-66, C2-68 to C2-70, C2-72 to C2-74, C2-76 to C2-78, C2-80 to C2-82, C2-84 to C2-86, C3-1 to C3-66, C4-1 to C4-33, C4-35 to C4-37, C4-39 to C4-41, C4-43 to C4-45, C4-47 to C4-49, C4-51 to C4-53, C4-55 to C4-57, C4-59 to C4-61, C4-63 to C4-65, C5-1 to C5-66, C6-1 to C6-33, C6-35 to C6-37, C6-39 to C6-41, C6-43 to C6-45, C6-47 to C6-49, C6-51 to C6-53, C6-55 to C6-57, C6-59 to C6-61 and C6-63 to C6-65: TABLE-US-00015 Com- Com- pound Formula R.sub.11 R.sub.12 pound Formula R.sub.11 R.sub.12 C1-1 7 R.sub.aa R.sub.aa C1-2 7 R.sub.ab R.sub.aa C1-3 7 R.sub.ac R.sub.aa C1-4 7 R.sub.ad R.sub.aa C1-5 7 R.sub.ae R.sub.aa C1-6 7 R.sub.aa R.sub.ab C1-7 7 R.sub.ab R.sub.ab C1-8 7 R.sub.ac R.sub.ab C1-9 7 R.sub.ad R.sub.ab C1-10 7 R.sub.ae R.sub.ab C1-11 7 R.sub.aa R.sub.ac C1-12 7 R.sub.ab R.sub.ac C1-13 7 R.sub.ac R.sub.ac C1-14 7 R.sub.ad R.sub.ac C1-15 7 R.sub.ae R.sub.ac C1-16 7 R.sub.aa R.sub.af C1-17 7 R.sub.ab R.sub.af C1-18 7 R.sub.ac R.sub.af C1-19 7 R.sub.ad R.sub.af C1-20 7 R.sub.ae R.sub.af C1-21 7 R.sub.aa R.sub.ag C1-22 7 R.sub.ab R.sub.ag C1-23 7 R.sub.ac R.sub.ag C1-24 7 R.sub.ad R.sub.ag C1-25 7 R.sub.ae R.sub.ag C1-26 7 R.sub.aa R.sub.ah C1-27 7 R.sub.ab R.sub.ah C1-28 7 R.sub.ac R.sub.ah C1-29 7 R.sub.ad R.sub.ah C1-30 7 R.sub.ae R.sub.ah C1-31 7 R.sub.aa R.sub.ai C1-32 7 R.sub.ab R.sub.ai C1-33 7 R.sub.ac R.sub.ai C1-34 7 R.sub.ad R.sub.ai C1-35 7 R.sub.ae R.sub.ai C1-36 7 R.sub.aa R.sub.aj C1-37 7 R.sub.ab R.sub.aj C1-38 7 R.sub.ac R.sub.aj C1-39 7 R.sub.ad R.sub.aj C1-40 7 R.sub.ae R.sub.aj C1-41 7 R.sub.aa R.sub.ak C1-42 7 R.sub.ab R.sub.ak C1-43 7 R.sub.ac R.sub.ak C1-44 7 R.sub.ad R.sub.ak C1-45 7 R.sub.ae R.sub.ak C1-46 7 R.sub.aa R.sub.al C1-47 7 R.sub.ab R.sub.al C1-48 7 R.sub.ac R.sub.al C1-49 7 R.sub.ad R.sub.al C1-50 7 R.sub.ae R.sub.al C1-51 7 R.sub.aa R.sub.am C1-52 7 R.sub.ab R.sub.am C1-53 7 R.sub.ac R.sub.am C1-54 7 R.sub.ad R.sub.am C1-55 7 R.sub.ae R.sub.am C1-56 7 R.sub.aa R.sub.an C1-57 7 R.sub.ab R.sub.an C1-58 7 R.sub.ac R.sub.an C1-59 7 R.sub.ad R.sub.an C1-60 7 R.sub.ae R.sub.an C1-61 7 R.sub.aa R.sub.ao C1-62 7 R.sub.ab R.sub.ao C1-63 7 R.sub.ak R.sub.ao C1-64 7 R.sub.an R.sub.ao C1-65 7 R.sub.aa R.sub.ap C1-66 7 R.sub.ab R.sub.ap C1-67 7 R.sub.ak R.sub.ap C1-68 7 R.sub.an R.sub.ap C1-69 7 R.sub.aa R.sub.aq C1-70 7 R.sub.ab R.sub.aq C1-71 7 R.sub.ak R.sub.aq C1-72 7 R.sub.an R.sub.aq C1-73 7 R.sub.aa R.sub.ar C1-74 7 R.sub.ab R.sub.ar C1-75 7 R.sub.ak R.sub.ar C1-76 7 R.sub.an R.sub.ar C1-77 7 R.sub.aa R.sub.as C1-78 7 R.sub.ab R.sub.as C1-79 7 R.sub.ak R.sub.as C1-80 7 R.sub.an R.sub.as C1-81 7 R.sub.aa R.sub.at C1-82 7 R.sub.ab R.sub.at C1-83 7 R.sub.ak R.sub.at C1-84 7 R.sub.an R.sub.at C1-85 7 R.sub.aa R.sub.au C1-86 7 R.sub.ab R.sub.au C1-87 7 R.sub.ak R.sub.au C1-88 7 R.sub.an R.sub.au C1-89 7 R.sub.aa R.sub.av C1-90 7 R.sub.ab R.sub.av C1-91 7 R.sub.ak R.sub.av C1-92 7 R.sub.an R.sub.av C1-93 7 R.sub.aa R.sub.aw C1-94 7 R.sub.ab R.sub.aw C1-95 7 R.sub.ak R.sub.aw C1-96 7 R.sub.an R.sub.aw C2-1 7 R.sub.aa R.sub.ad C2-2 7 R.sub.aa R.sub.ae C2-3 7 R.sub.ab R.sub.ad C2-4 7 R.sub.ab R.sub.ae C2-5 7 R.sub.ac R.sub.ad C2-6 7 R.sub.ac R.sub.ae C2-7 7 R.sub.af R.sub.aa C2-8 7 R.sub.af R.sub.ab C2-9 7 R.sub.af R.sub.ac C2-10 7 R.sub.af R.sub.ad C2-11 7 R.sub.af R.sub.ae C2-12 7 R.sub.ag R.sub.aa C2-13 7 R.sub.ag R.sub.ab C2-14 7 R.sub.ag R.sub.ac C2-15 7 R.sub.ag R.sub.ad C2-16 7 R.sub.ag R.sub.ae C2-17 7 R.sub.ah R.sub.aa C2-18 7 R.sub.ah R.sub.ab C2-19 7 R.sub.ah R.sub.ac C2-20 7 R.sub.ah R.sub.ad C2-21 7 R.sub.ah R.sub.ae C2-22 7 R.sub.ai R.sub.aa C2-23 7 R.sub.ai R.sub.ab C2-24 7 R.sub.ai R.sub.ac C2-25 7 R.sub.ai R.sub.ad C2-26 7 R.sub.ai R.sub.ae C2-27 7 R.sub.aj R.sub.aa C2-28 7 R.sub.aj R.sub.ab C2-29 7 R.sub.aj R.sub.ac C2-30 7 R.sub.aj R.sub.ad C2-31 7 R.sub.aj R.sub.ae C2-32 7 R.sub.ak R.sub.aa C2-33 7 R.sub.ak R.sub.ab C2-34 7 R.sub.ak R.sub.ac C2-35 7 R.sub.ak R.sub.ad C2-36 7 R.sub.ak R.sub.ae C2-37 7 R.sub.al R.sub.aa C2-38 7 R.sub.al R.sub.ab C2-39 7 R.sub.al R.sub.ac C2-40 7 R.sub.al R.sub.ad C2-41 7 R.sub.al R.sub.ae C2-42 7 R.sub.am R.sub.aa C2-43 7 R.sub.am R.sub.ab C2-44 7 R.sub.am R.sub.ac C2-45 7 R.sub.am R.sub.ad C2-46 7 R.sub.am R.sub.ae C2-47 7 R.sub.an R.sub.aa C2-48 7 R.sub.an R.sub.ab C2-49 7 R.sub.an R.sub.ac C2-50 7 R.sub.an R.sub.ad C2-51 7 R.sub.an R.sub.ae C2-52 7 R.sub.ao R.sub.aa C2-53 7 R.sub.ao R.sub.ad C2-54 7 R.sub.ao R.sub.ae C2-56 7 R.sub.ap R.sub.aa C2-57 7 R.sub.ap R.sub.ad C2-58 7 R.sub.ap R.sub.ae C2-60 7 R.sub.aq R.sub.aa C2-61 7 R.sub.aq R.sub.ad C2-62 7 R.sub.aq R.sub.ae C2-64 7 R.sub.ar R.sub.aa C2-65 7 R.sub.ar R.sub.ad C2-66 7 R.sub.ar R.sub.ae C2-68 7 R.sub.as R.sub.aa C2-69 7 R.sub.as R.sub.ad C2-70 7 R.sub.as R.sub.ae C2-72 7 R.sub.at R.sub.aa C2-73 7 R.sub.at R.sub.ad C2-74 7 R.sub.at R.sub.ae C2-76 7 R.sub.au R.sub.aa C2-77 7 R.sub.au R.sub.ad C2-78 7 R.sub.au R.sub.ae C2-80 7 R.sub.av R.sub.aa C2-81 7 R.sub.av R.sub.ad C2-82 7 R.sub.av R.sub.ae C2-84 7 R.sub.aw R.sub.aa C2-85 7 R.sub.aw R.sub.ad C2-86 7 R.sub.aw R.sub.ae — — — — C3-1 8 R.sub.aa R.sub.aa C3-2 8 R.sub.ac R.sub.aa C3-3 8 R.sub.ad R.sub.aa C3-4 8 R.sub.ay R.sub.aa C3-5 8 R.sub.am R.sub.aa C3-6 8 R.sub.aa R.sub.ab C3-7 8 R.sub.ac R.sub.ab C3-8 8 R.sub.ad R.sub.ab C3-9 8 R.sub.ay R.sub.ab C3-10 8 R.sub.am R.sub.ab C3-11 8 R.sub.aa R.sub.ac C3-12 8 R.sub.ac R.sub.ac C3-13 8 R.sub.ad R.sub.ac C3-14 8 R.sub.ay R.sub.ac C3-15 8 R.sub.am R.sub.ac C3-16 8 R.sub.aa R.sub.ak C3-17 8 R.sub.ac R.sub.ak C3-18 8 R.sub.ad R.sub.ak C3-19 8 R.sub.ay R.sub.ak C3-20 8 R.sub.am R.sub.ak C3-21 8 R.sub.aa R.sub.az C3-22 8 R.sub.ac R.sub.az C3-23 8 R.sub.ad R.sub.az C3-24 8 R.sub.ay R.sub.az C3-25 8 R.sub.am R.sub.az C3-26 8 R.sub.aa R.sub.ae C3-27 8 R.sub.ac R.sub.ae C3-28 8 R.sub.ad R.sub.ae C3-29 8 R.sub.ay R.sub.ae C3-30 8 R.sub.am R.sub.ae C3-31 8 R.sub.aa R.sub.ao C3-32 8 R.sub.ab R.sub.ao C3-33 8 R.sub.ak R.sub.ao C3-34 8 R.sub.an R.sub.ao C3-35 8 R.sub.aa R.sub.ap C3-36 8 R.sub.ab R.sub.ap C3-37 8 R.sub.ak R.sub.ap C3-38 8 R.sub.an R.sub.ap C3-39 8 R.sub.aa R.sub.aq C3-40 8 R.sub.ab R.sub.aq C3-41 8 R.sub.ak R.sub.aq C3-42 8 R.sub.an R.sub.aq C3-43 8 R.sub.aa R.sub.ar C3-44 8 R.sub.ab R.sub.ar C3-45 8 R.sub.ak R.sub.ar C3-46 8 R.sub.an R.sub.ar C3-47 8 R.sub.aa R.sub.as C3-48 8 R.sub.ab R.sub.as C3-49 8 R.sub.ak R.sub.as C3-50 8 R.sub.an R.sub.as C3-51 8 R.sub.aa R.sub.at C3-52 8 R.sub.ab R.sub.at C3-53 8 R.sub.ak R.sub.at C3-54 8 R.sub.an R.sub.at C3-55 8 R.sub.aa R.sub.au C3-56 8 R.sub.ab R.sub.au C3-57 8 R.sub.ak R.sub.au C3-58 8 R.sub.an R.sub.au C3-59 8 R.sub.aa R.sub.av C3-60 8 R.sub.ab R.sub.av C3-61 8 R.sub.ak R.sub.av C3-62 8 R.sub.an R.sub.av C3-63 8 R.sub.aa R.sub.aw C3-64 8 R.sub.ab R.sub.aw C3-65 8 R.sub.ak R.sub.aw C3-66 8 R.sub.an R.sub.aw C4-1 9 R.sub.aa R.sub.aa C4-2 9 R.sub.ab R.sub.aa C4-3 9 R.sub.ad R.sub.aa C4-4 9 R.sub.ay R.sub.aa C4-5 9 R.sub.am R.sub.aa C4-6 9 R.sub.aa R.sub.ab C4-7 9 R.sub.ab R.sub.ab C4-8 9 R.sub.ad R.sub.ab C4-9 9 R.sub.ay R.sub.ab C4-10 9 R.sub.am R.sub.ab C4-11 9 R.sub.aa R.sub.ac C4-12 9 R.sub.ab R.sub.ac C4-13 9 R.sub.ad R.sub.ac C4-14 9 R.sub.ay R.sub.ac C4-15 9 R.sub.am R.sub.ac C4-16 9 R.sub.aa R.sub.ak C4-17 9 R.sub.ab R.sub.ak C4-18 9 R.sub.ad R.sub.ak C4-19 9 R.sub.ay R.sub.ak C4-20 9 R.sub.am R.sub.ak C4-21 9 R.sub.aa R.sub.az C4-22 9 R.sub.ab R.sub.az C4-23 9 R.sub.ad R.sub.az C4-24 9 R.sub.ay R.sub.az C4-25 9 R.sub.am R.sub.az C4-26 9 R.sub.aa R.sub.ae C4-27 9 R.sub.ab R.sub.ae C4-28 9 R.sub.ad R.sub.ae C4-29 9 R.sub.ay R.sub.ae C4-30 9 R.sub.am R.sub.ae C4-31 9 R.sub.aa R.sub.ao C4-32 9 R.sub.ad R.sub.ao C4-33 9 R.sub.ae R.sub.ao C4-35 9 R.sub.aa R.sub.ap C4-36 9 R.sub.ad R.sub.ap C4-37 9 R.sub.ae R.sub.ap C4-39 9 R.sub.aa R.sub.aq C4-40 9 R.sub.ad R.sub.aq C4-41 9 R.sub.ae R.sub.aq C4-43 9 R.sub.aa R.sub.ar C4-44 9 R.sub.ad R.sub.ar C4-45 9 R.sub.ae R.sub.ar C4-47 9 R.sub.aa R.sub.as C4-48 9 R.sub.ad R.sub.as C4-49 9 R.sub.ae R.sub.as C4-51 9 R.sub.aa R.sub.at C4-52 9 R.sub.ad R.sub.at C4-53 9 R.sub.ae R.sub.at C4-55 9 R.sub.aa R.sub.au C4-56 9 R.sub.ad R.sub.au C4-57 9 R.sub.ae R.sub.au C4-59 9 R.sub.aa R.sub.av C4-60 9 R.sub.ad R.sub.av C4-61 9 R.sub.ae R.sub.av C4-63 9 R.sub.aa R.sub.aw C4-64 9 R.sub.ad R.sub.aw C4-65 9 R.sub.ae R.sub.aw C5-1 10 R.sub.aa R.sub.aa C5-2 10 R.sub.ab R.sub.aa C5-3 10 R.sub.ad R.sub.aa C5-4 10 R.sub.ay R.sub.aa C5-5 10 R.sub.am R.sub.aa C5-6 10 R.sub.aa R.sub.ab C5-7 10 R.sub.ab R.sub.ab C5-8 10 R.sub.ad R.sub.ab C5-9 10 R.sub.ay R.sub.ab C5-10 10 R.sub.am R.sub.ab C5-11 10 R.sub.aa R.sub.ac C5-12 10 R.sub.ab R.sub.ac C5-13 10 R.sub.ad R.sub.ac C5-14 10 R.sub.ay R.sub.ac C5-15 10 R.sub.am R.sub.ac C5-16 10 R.sub.aa R.sub.ak C5-17 10 R.sub.ab R.sub.ak C5-18 10 R.sub.ad R.sub.ak C5-19 10 R.sub.ay R.sub.ak C5-20 10 R.sub.am R.sub.ak C5-21 10 R.sub.aa R.sub.an C5-22 10 R.sub.ab R.sub.an C5-23 10 R.sub.ad R.sub.an C5-24 10 R.sub.ay R.sub.an C5-25 10 R.sub.am R.sub.an C5-26 10 R.sub.aa R.sub.ae C5-27 10 R.sub.ab R.sub.ae C5-28 10 R.sub.ad R.sub.ae C5-29 10 R.sub.ay R.sub.ae C5-30 10 R.sub.am R.sub.ae C5-31 10 R.sub.aa R.sub.ao C5-32 10 R.sub.ab R.sub.ao C5-33 10 R.sub.ak R.sub.ao C5-34 10 R.sub.an R.sub.ao C5-35 10 R.sub.aa R.sub.ap C5-36 10 R.sub.ab R.sub.ap C5-37 10 R.sub.ak R.sub.ap C5-38 10 R.sub.an R.sub.ap C5-39 10 R.sub.aa R.sub.aq C5-40 10 R.sub.ab R.sub.aq C5-41 10 R.sub.ak R.sub.aq C5-42 10 R.sub.an R.sub.aq C5-43 10 R.sub.aa R.sub.ar C5-44 10 R.sub.ab R.sub.ar C5-45 10 R.sub.ak R.sub.ar C5-46 10 R.sub.an R.sub.ar C5-47 10 R.sub.aa R.sub.as C5-48 10 R.sub.ab R.sub.as C5-49 10 R.sub.ak R.sub.as C5-50 10 R.sub.an R.sub.as C5-51 10 R.sub.aa R.sub.at C5-52 10 R.sub.ab R.sub.at C5-53 10 R.sub.ak R.sub.at C5-54 10 R.sub.an R.sub.at C5-55 10 R.sub.aa R.sub.au C5-56 10 R.sub.ab R.sub.au C5-57 10 R.sub.ak R.sub.au C5-58 10 R.sub.an R.sub.au C5-59 10 R.sub.aa R.sub.av C5-60 10 R.sub.ab R.sub.av C5-61 10 R.sub.ak R.sub.av C5-62 10 R.sub.an R.sub.av C5-63 10 R.sub.aa R.sub.aw C5-64 10 R.sub.ab R.sub.aw C5-65 10 R.sub.ak R.sub.aw C5-66 10 R.sub.an R.sub.aw C6-1 11 R.sub.aa R.sub.aa C6-2 11 R.sub.ac R.sub.aa C6-3 11 R.sub.ad R.sub.aa C6-4 11 R.sub.ay R.sub.aa C6-5 11 R.sub.am R.sub.aa C6-6 11 R.sub.aa R.sub.ab C6-7 11 R.sub.ac R.sub.ab C6-8 11 R.sub.ad R.sub.ab C6-9 11 R.sub.ay R.sub.ab C6-10 11 R.sub.am R.sub.ab C6-11 11 R.sub.aa R.sub.ac C6-12 11 R.sub.ac R.sub.ac C6-13 11 R.sub.ad R.sub.ac C6-14 11 R.sub.ay R.sub.ac C6-15 11 R.sub.am R.sub.ac C6-16 11 R.sub.aa R.sub.ak C6-17 11 R.sub.ac R.sub.ak C6-18 11 R.sub.ad R.sub.ak C6-19 11 R.sub.ay R.sub.ak C6-20 11 R.sub.am R.sub.ak C6-21 11 R.sub.aa R.sub.az C6-22 11 R.sub.ac R.sub.az C6-23 11 R.sub.ad R.sub.az C6-24 11 R.sub.ay R.sub.az C6-25 11 R.sub.am R.sub.az C6-26 11 R.sub.aa R.sub.ae C6-27 11 R.sub.ac R.sub.ae C6-28 11 R.sub.ad R.sub.ae C6-29 11 R.sub.ay R.sub.ae C6-30 11 R.sub.am R.sub.ae C6-31 11 R.sub.aa R.sub.ao C6-32 11 R.sub.ad R.sub.ao C6-33 11 R.sub.ae R.sub.ao C6-35 11 R.sub.aa R.sub.ap C6-36 11 R.sub.ad R.sub.ap C6-37 11 R.sub.ae R.sub.ap C6-39 11 R.sub.aa R.sub.aq C6-40 11 R.sub.ad R.sub.aq C6-41 11 R.sub.ae R.sub.aq C6-43 11 R.sub.aa R.sub.ar C6-44 11 R.sub.ad R.sub.ar C6-45 11 R.sub.ae R.sub.ar C6-47 11 R.sub.aa R.sub.as C6-48 11 R.sub.ad R.sub.as C6-49 11 R.sub.ae R.sub.as C6-51 11 R.sub.aa R.sub.at C6-52 11 R.sub.ad R.sub.at C6-53 11 R.sub.ae R.sub.at C6-55 11 R.sub.aa R.sub.au C6-56 11 R.sub.ad R.sub.au C6-57 11 R.sub.ae R.sub.au C6-59 11 R.sub.aa R.sub.av C6-60 11 R.sub.ad R.sub.av C6-61 11 R.sub.ae R.sub.av C6-63 11 R.sub.aa R.sub.aw C6-64 11 R.sub.ad R.sub.aw C6-65 11 R.sub.ae R.sub.aw wherein each of compounds C1-1 to C1-96, C2-1 to C2-54, C2-56 to C2-58, C2-60 to C2-62, C2-64 to C2-66, C2-68 to C2-70, C2-72 to C2-74, C2-76 to C2-78, C2-80 to C2-82, C2-84 to C2-86, C3-1 to C3-66, C4-1 to C4-33, C4-35 to C4-37, C4-39 to C4-41, C4-43 to C4-45, C4-47 to C4-49, C4-51 to C4-53, C4-55 to C4-57, C4-59 to C4-61, C4-63 to C4-65, C5-1 to C5-66, C6-1 to C6-33, C6-35 to C6-37, C6-39 to C6-41, C6-43 to C6-45, C6-47 to C6-49, C6-51 to C6-53, C6-55 to C6-57, C6-59 to C6-61 and C6-63 to C6-65 is represented by any one of formulas 7 to 11, and R and R.sub.12, each independently, are any one of the following R.sub.aa to R.sub.aw, R.sub.ay, R.sub.az and R.sub.ba to R.sub.bi: ##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190## ##STR00191##

Description

Example 1: Preparation of Compound C1-4

(1) ##STR00148## ##STR00149##

(2) Synthesis of Compound 1-1

(3) 8.5 g of 5-bromo-7H-dibenzo[c,g]carbazole (0.025 mol), 10.7 g of 2-iodo-naphthalene (0.042 mol), 1.49 g of ethylenediamine (EDA) (0.025 mol), 13.1 g of K.sub.3PO.sub.4 (0.062 mol), and 2.3 g of CuI (0.012 mol) were placed in 124 mL of toluene, and the mixture was stirred under reflux for one day. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with methylene chloride (MC). Thereafter, the extracted organic layer was distilled under reduced pressure and then purified by column chromatography with MC/Hex to obtain 7.6 g of compound 1-1 (yield: 58%).

(4) Synthesis of Compound 1-2

(5) 7.5 g of compound 1-1 (0.016 mol), 2.4 g of 2-chloro-benzeneamine (0.019 mol), 0.36 g of Pd(OAc).sub.2 (0.002 mol), 0.15 g of P(t-Bu).sub.3 (0.003 mol), and 3.8 g of NaOt-Bu (0.04 mol) were placed in 80 mL of toluene, and the mixture was stirred at 100° C. for one day. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and EA. The extracted organic layer was distilled under reduced pressure, and then purified by column chromatography with MC/Hex to obtain 3.6 g of compound 1-2 (yield: 43%).

(6) Synthesis of Compound 1-3

(7) 5.8 g of compound 1-2 (0.011 mol), 0.82 g of P(Cy).sub.3HBF.sub.4 (0.002 mol), 0.25 g of Pd(OAc).sub.2 (0.001 mol), and 10.9 g of Cs.sub.2CO.sub.3 (0.033 mol) were placed in 44.4 mL of DMA, and the mixture was stirred under reflux for one day. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and MC. The extracted organic layer was distilled under reduced pressure, and then purified by column chromatography with MC/Hex to obtain 4.2 g of compound 1-3 (yield: 76%).

(8) Synthesis of Compound 1-4

(9) 4.2 g of compound 1-3 (0.009 mol), 1.9 mL of iodobenzene (0.017 mol), 0.8 g of CuI (0.004 mol), 2 mL of 1,2-diaminocyclohexane (0.018 mol), and 3.7 g of K.sub.3PO.sub.4 (0.017 mol) were placed in 44 mL of o-xylene, and the mixture was stirred under reflux for one day. After extracting with MC, the reaction mixture was distilled under reduced pressure. Thereafter, the residue was purified by column chromatography with MC/Hex to obtain 1.2 g of compound C1-4 (yield: 24%).

(10) .sup.1H NMR (600 MHz, DMSO,δ) 9.19-9.07 (d, 1H), 9.01-9.00 (d, 1H), 8.37 (s, 1H), 8.35-8.34 (d, 1H), 8.23-8.22 (d, 1H), 8.15-8.14 (d, 1H), 8.06-8.05 (d, 1H), 7.94-7.92 (m, 2H), 7.78-7.56 (m, 12H), 7.30-7.27 (t, 1H), 7.11-7.09 (t, 1H), 7.05-7.04 (d, 1H), 6.41-6.39 (t, 1H), 5.88-5.86 (d, 1H)

(11) TABLE-US-00002 MW M.P. C1-4 558.7 272.6° C.

Example 2: Preparation of Compound C1-11

(12) ##STR00150##

(13) Synthesis of Compound 2-1

(14) 100 g of 7H-dibenzo[c,g]carbazole (374 mmol) was dissolved in 1.8 L of DMF, and the mixture was cooled and stirred at 0° C. 60 g of N-bromosuccinimide (336 mmol) was dissolved in 200 mL of DMF, and the mixture was added dropwise for 2.5 hours. The mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was washed with Na.sub.2S.sub.2O.sub.3 aqueous solution and water. The organic layer was extracted with ethyl acetate, and the residual moisture was removed by using MgSO.sub.4. The residue was dried and purified by silica filter to obtain 106 g of compound 2-1 (yield: 82%).

(15) Synthesis of Compound 2-2

(16) 15 g of compound 2-1 (43.32 mmol), 17.6 g of iodobenzene (86.65 mmol), 2.6 g of EDA (43.32 mmol), 23 g of K.sub.3PO.sub.4 (108.3 mmol), and 4.1 g of CuI (21.66 mmol) were placed in 216 mL of toluene, and the mixture was stirred under reflux for one day. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with MC. Thereafter, the extracted organic layer was distilled under reduced pressure, and then purified by column chromatography with MC/Hex to obtain 9 g of compound 2-2 (yield: 50%).

(17) Synthesis of Compound 2-3

(18) 9 g of compound 2-2 (21.31 mmol), 4 g of 2-chloro-benzeneamine (31.96 mmol), 0.47 g of Pd(OAc).sub.2 (2.131 mmol), 0.86 g of P(t-Bu).sub.3 (4.262 mmol), and 5.1 g of NaOt-Bu (53.27 mmol) were placed in 108 mL of toluene, and the mixture was stirred at 140° C. for one day. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and EA. The extracted organic layer was distilled under reduced pressure, and then purified by column chromatography with MC/Hex to obtain 7.5 g of compound 2-3 (yield: 75%).

(19) Synthesis of Compound 2-4

(20) 7.5 g of compound 2-3 (16.02 mmol), 1.17 g of P(Cy).sub.3HBF.sub.4 (3.204 mmol), 0.36 g of Pd(OAc).sub.2 (1.602 mmol), and 15.65 g of Cs.sub.2CO.sub.3 (48.06 mmol) were placed in 80 mL of DMA, and the mixture was stirred under reflux for one day. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and MC. The extracted organic layer was distilled under reduced pressure, and then purified by column chromatography with MC/Hex to obtain 4 g of compound 2-4 (yield: 58%).

(21) Synthesis of Compound C1-11

(22) 4 g of compound 2-4 (9.25 mmol), 3.1 g of 3-iodo-1,1′-biphenyl (11.1 mmol), 0.42 g of Pd.sub.2(dba).sub.3 (0.46 mmol), 0.38 g of s-phos (0.92 mmol), and 2.2 g of NaOt-Bu (23.13 mmol) were placed in 46 mL of o-xylene, and the mixture was stirred under reflux for one day. The reaction mixture was extracted with MC, and then distilled under reduced pressure. Thereafter, the residue was purified by column chromatography with MC/Hex to obtain 1.2 g of compound C1-11 (yield: 23%).

(23) .sup.1H NMR (600 MHz,DMSO,δ) 9.17-915 (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)

(24) TABLE-US-00003 MW M.P. C1-11 584.7 249.6° C.

Example 3: Preparation of Compound C1-1

(25) ##STR00151## ##STR00152##

(26) Synthesis of Compound 3-1

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

(28) Synthesis of Compound 3-2

(29) 76 g of compound 3-1 (5-bromo-7H-dibenzo[c,g]carbazole) (220 mmol), 90 g of iodobenzene (439 mmol), 20.90 g of CuI (110 mmol), 13 g of ethylenediamine (110 mmol), and 139 g of K.sub.3PO.sub.4 (659 mmol) were placed in 1.1 L of toluene, and the mixture was stirred under reflux for 2.5 hours. After adding MeOH, the resultant solid was filtered under reduced pressure. Thereafter, the residue was purified by column chromatography to obtain 55.1 g of compound 3-2 (yield: 60%).

(30) Synthesis of Compound 3-3

(31) 54.6 g of compound 3-2 (129 mmol), 20 g of 2-chloroaniline (155 mmol), 2.9 g of Pd(OAc).sub.2 (13 mmol), 5.2 g of P(t-Bu).sub.3 (26 mmol), and 31 g of NaOt-Bu (323 mmol) were placed in 650 mL of toluene, and the mixture was stirred under reflux for 4 hours. The reaction mixture was cooled to room temperature, and NH.sub.4Cl(aq) was added. The reaction mixture was extracted with EA, and then dried with magnesium sulfate. The extracted organic layer was distilled under reduced pressure, and then purified by column chromatography to obtain 47.9 g of compound 3-3 (yield: 79%).

(32) Synthesis of Compound 3-4

(33) 48 g of compound 3-3 (103 mmol), 2.3 g of Pd(OAc).sub.2 (10 mmol), 7.6 g of ligand (tricyclohexylphosphonium tetrafluoroborate) (21 mmol), and 100 g of Cs.sub.2CO.sub.3 (308 mmol) were placed in 400 mL of DMA, and the mixture was stirred under reflux for 1 hour. The reaction mixture was cooled to room temperature, and NH.sub.4Cl(aq) was added. The reaction mixture was extracted with MC, and then dried with magnesium sulfate. The extracted organic layer was distilled under reduced pressure, and then purified by column chromatography to obtain 44 g of compound 3-4 (yield: 79%).

(34) Synthesis of Compound C1-1

(35) 5 g of compound 3-4 (12 mmol), 3.5 g of iodobenzene (17 mmol), 1.1 g of CuI (6 mmol), 2.6 g of 1,2-diaminocyclohexane (23 mmol), and 4.9 g of K.sub.3PO.sub.4 (23 mmol) were placed in 60 mL of o-xylene, and the mixture was stirred under reflux for one day. The reaction mixture was cooled to room temperature, and filtered through celite with MC. The filtrate was distilled under reduced pressure, and then purified by column chromatography with MC/Hex to obtain 1.3 g of compound C1-1 (yield: 22%).

(36) H 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)

(37) TABLE-US-00004 MW M.P. C1-1 508.62 184° C.

Example 4: Preparation of Compound C2-1

(38) ##STR00153##

(39) 7 g of compound 4-1 (16 mmol), 6.7 g of 2-bromonaphthalene (32 mmol), 1.5 g of CuI (8 mmol), 3.7 g of 1,2-diaminocyclohexane (32 mmol), and 10.3 g of K.sub.3PO.sub.4 (49 mmol) were placed in 80 mL of o-xylene, and the mixture was stirred under reflux for one day. The reaction mixture was cooled to room temperature, and filtered through celite with MC. The filtrate was distilled under reduced pressure, and then purified by column chromatography with MC/Hex to obtain 1.3 g of compound C2-1 (yield: 22%).

(40) .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)

(41) TABLE-US-00005 MW M.P. C2-1 558.68 263° C.

Example 5: Preparation of Compound C1-13

(42) ##STR00154## ##STR00155##

(43) Synthesis of Compound 5-2

(44) 15 g of compound 5-1 (5-bromo-7H-dibenzo[c,g]carbazole) (220 mmol), 18 g of 3-iodo-1,1′-biphenyl (65 mmol), 4.1 g of CuI (22 mmol), 2.6 g of ethylenediamine (43 mmol), and 23 g of K.sub.3PO.sub.4 (108 mmol) were placed in 216 mL of toluene, and the mixture was stirred under reflux for 4 hours. After adding MeOH, the resultant solid was filtered under reduced pressure. Thereafter, the filtrate was purified by column chromatography to obtain 16 g of compound 5-2 (74%).

(45) Synthesis of Compound 5-3

(46) 15 g of compound 5-2 (30 mmol), 7.7 g of 2-chloroaniline (60 mmol), 0.67 g of Pd(OAc).sub.2 (3 mmol), 1.2 g of P(t-Bu).sub.3 (6 mmol), and 7.2 g of NaOt-Bu (75 mmol) were placed in 150 mL of toluene, and the mixture was stirred under reflux for 2 hours. The reaction mixture was cooled to room temperature, and NH.sub.4Cl(aq) was added. Thereafter, the reaction mixture was extracted with EA, and then dried with magnesium sulfate. The extracted organic layer was distilled under reduced pressure, and then purified by column chromatography to obtain 10.1 g of compound 5-3 (62%).

(47) Synthesis of Compound 5-4

(48) 10 g of compound 5-3 (18 mmol), 0.41 g of Pd(OAc).sub.2 (1.8 mmol), 1.35 g of ligand (tricyclohexylphosphonium tetrafluoroborate) (3.7 mmol), and 18 g of Cs.sub.2CO.sub.3 (55 mmol) were placed in 92 mL of DMA, and the mixture was stirred under reflux for 1 hour. The reaction mixture was cooled to room temperature, and NH.sub.4Cl(aq) was added. The reaction mixture was extracted with MC, and then dried with magnesium sulfate. The extracted organic layer was distilled under reduced pressure, and then purified by column chromatography to obtain 7.1 g of compound 5-4 (76%).

(49) Synthesis of Compound C1-13

(50) 6.7 g of compound 5-4 (13 mmol), 7.4 g of 3-iodo-1,1′-biphenyl (26 mmol), 0.42 g of Cu powder (7 mmol), and 3.6 g of K.sub.2CO.sub.3 (26 mmol) were placed in 70 mL of o-dichlorobenzene, and the mixture was stirred under reflux for one day. The reaction mixture was cooled to room temperature, and filtered through celite with MC. The filtrate was distilled under reduced pressure, and then purified by column chromatography with MC/Hex to obtain 3.1 g of compound C1-13 (36%).

(51) H 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)

(52) TABLE-US-00006 MW M.P. C1-13 660.82 259° C.

Example 6: Preparation of Compound C1-65

(53) ##STR00156##

(54) 5.0 g of compound 6-4 (12 mmol), 6.7 g of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (17 mmol), 0.52 g of Pd.sub.2(dba).sub.3 (0.58 mmol), 0.48 g of S-phos (1 mmol), and 31 g of NaOt-Bu (29 mmol) were placed in 60 mL of o-xylene, and the mixture was stirred under reflux for 4 hours. The reaction mixture was cooled to room temperature, and MeOH was added. The resultant solid was filtered under reduced pressure, and purified by column chromatography to obtain 3.0 g of compound C1-65 (35%).

(55) .sup.1H NMR (600 MHz, CDCl.sub.3,δ) 9.20-9.18 (d, 1H), 9.13-9.12 (d, 2H), 8.14-8.13 (d, 1H), 9.02-9.01 (d, 1H), 8.84-8.83 (d, 1H), 8.16-8.15 (d, 1H), 7.97-7.95 (m, 3H), 7.83-7.80 (m, 5H), 7.77-7.57 (d, 11H), 7.34-7.32 (m, 1H), 7.28-7.25 (m, 2H), 6.83-6.81 (m, 1H), 5.99-5.97 (d, 1H)

(56) TABLE-US-00007 MW M.P. C1-65 739.88 345° C.

Example 7: Preparation of Compound C1-61

(57) ##STR00157##

(58) 5.0 g of compound 7-4 (12 mmol), 4.6 g of 2-chloro-4,6-diphenyl-1,3,5-triazine (17 mmol), 0.71 g of DMAP (6 mmol), and 4.0 g of K.sub.2CO.sub.3 (29 mmol) were placed in 80 mL of DMF and 60 mL of o-xylene, and the mixture was stirred under reflux for one day. The reaction mixture was cooled to room temperature, and MeOH was added. The resultant solid was filtered under reduced pressure, and purified by column chromatography to obtain 2.6 g of compound C1-61 (34%).

(59) .sup.1H NMR (600 MHz, CDCl.sub.3,δ) 9.22-9.21 (d, 1H), 9.17-9.16 (d, 1H), 8.66-8.65 (d, 1H), 8.56-8.55 (d, 4H), 8.19-817 (d, 1H), 8.01-8.00 (m, 1H), 7.83-7.79 (m, 6H), 7.74-7.57 (m, 10H), 7.45-7.38 (m, 2H), 6.92-6.91 (m, 1H), 5.97-5.95 (m, 1H)

(60) TABLE-US-00008 MW M.P. C1-61 663.78 311° C.

Example 8: Preparation of Compound C1-69

(61) ##STR00158##

(62) 5.0 g of compound 8-4 (12 mmol), 5.0 g of 2-chloro-4-phenylquinazoline (21 mmol), 0.52 g of Pd(OAc).sub.2 (0.81 mmol), 0.71 g of Sphos (2 mmol), and 1.1 g of NaOt-Bu (12 mmol) were placed in 100 mL of o-xylene, and the mixture was stirred under reflux for 5 hours. The reaction mixture was cooled to room temperature, and MeOH was added. The resultant solid was filtered under reduced pressure, and purified by column chromatography to obtain 1.4 g of compound C1-69 (19%).

(63) .sup.1H NMR (600 MHz, CDCl.sub.3,δ) 9.18-9.17 (d, 1H), 9.07-9.06 (d, 1H), 8.26-8.23 (m, 2H), 8.19-8.15 (m, 2H), 8.06-8.04 (m, 1H), 7.97-7.96 (m, 1H), 7.91-7.88 (m, 1H), 7.83-7.78 (m, 7H), 7.74-7.71 (m, 1H), 7.68-7.55 (m, 5H), 7.45-7.44 (m, 1H), 7.35-7.29 (m, 2H), 6.86-6.83 (t, 1H), 5.94-5.93 (d, 1H)

(64) TABLE-US-00009 MW M.P. C1-69 636.76 297° C.

Example 9: Preparation of Compound C2-52

(65) ##STR00159## ##STR00160##

(66) Synthesis of Compound 9-2

(67) 20 g of compound 1-1 (5-bromo-7H-dibenzo[c,g]carbazole) (58 mmol), 18.6 g of 2-chloro-4,6-diphenyl-1,3,5-triazine (69 mmol), 3.5 g of DMAP (29 mmol), and 20 g of K.sub.2CO.sub.3 (145 mmol) were placed in 290 mL of DMF, and the mixture was stirred at 100° C. for 1.5 hours. After adding MeOH, the resultant solid was filtered under reduced pressure. Thereafter, the residue was purified by column chromatography to obtain 26 g of compound 9-2 (78%).

(68) Synthesis of Compound 9-3

(69) 18.0 g of compound 9-2 (31 mmol), 4.8 g of 2-chloroaniline (37 mmol), 0.7 g of Pd(OAc).sub.2 (3 mmol), 1.3 g of P(t-Bu).sub.3 (6 mmol), and 7.5 g of NaOt-Bu (78 mmol) were placed in 150 mL of toluene, and the mixture was stirred under reflux for 2 hours. The reaction mixture was cooled to room temperature, and MeOH was added. The resultant solid was filtered under reduced pressure, and purified by column chromatography to obtain 18.0 g of compound 9-3 (93%).

(70) Synthesis of Compound 9-4

(71) 17.5 g of compound 9-3 (28 mmol), 0.7 g of Pd(OAc).sub.2 (3 mmol), 2.1 g of ligand (tricyclohexylphosphonium tetrafluoroborate) (6 mmol), and 27.4 g of Cs.sub.2CO.sub.3 (84 mmol) were placed in 112 mL of DMA, and the mixture was stirred under reflux for 2 hours. The reaction mixture was cooled to room temperature, and NH.sub.4Cl(aq) was added. The reaction mixture was extracted with MC, and then dried with magnesium sulfate. The extracted organic layer was distilled under reduced pressure, and then purified by column chromatography to obtain 6.1 g of compound 9-4 (37%).

(72) Synthesis of Compound C2-52

(73) 5.6 g of compound 9-4 (10 mmol), 2.9 g of iodobenzene (14 mmol), 0.9 g of CuI (5 mmol), 2.2 g of 1,2-diaminocyclohexane (19 mmol), and 4.0 g of K.sub.3PO.sub.4 (19 mmol) were placed in 95 mL of o-xylene, and the mixture was stirred for one day. The reaction mixture was cooled to room temperature, and MeOH was added. The resultant solid was filtered under reduced pressure, and purified by column chromatography to obtain 1.0 g of compound C2-52 (16%).

(74) .sup.1H NMR (600 MHz,DMSO,δ) 9.12-9.10 (d, 1H), 9.08-9.06 (d, 1H), 8.96-8.95 (d, 1H), 8.40-8.38 (m, 4H), 8.22-8.18 (m, 2H), 7.85-7.83 (m, 2H), 7.80-7.79 (d, 1H), 7.78-7.74 (m, 3H), 7.73-7.64 (m, 5H), 7.57-7.55 (m, 4H), 7.42-7.40 (t, 1H), 7.20-7.19 (t, 1H), 7.15-7.14 (d, 1H) 6.92-6.89 (t, 1H), 6.87-6.86 (d, 1H)

(75) TABLE-US-00010 MW M.P. C2-61 663.78 327° C.

(76) Hereinafter, the driving voltage, the luminous efficiency and the lifespan properties of an OLED including the compound represented by formula 1 will be explained. 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.

Comparative Example 1: Producing a Red Light-Emitting OLED not According to the Present Disclosure

(77) An OLED not 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 was introduced into a cell of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was then controlled to 10.sup.−7 torr. Thereafter, an electric current was applied to the cell to evaporate the above-introduced material, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate. Next, compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer. Compound HT-1 was then introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer. Compound HT-3 was then introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After forming the hole injection layers and the hole transport layers, a light-emitting layer was formed thereon as follows: Compound C was introduced into one cell of the vacuum vapor depositing apparatus as a host, and compound D-39 was introduced into another cell as a dopant. The two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 3 wt % based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer. Compound ET-1:compound EI-1 as an electron transport material was then deposited on the light-emitting layer at a weight ratio of 50:50 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 compounds used for producing the OLED were purified by vacuum sublimation at 10.sup.−6 torr.

Device Example 1: Producing a Red Light-Emitting OLED Comprising a Compound According to the Present Disclosure

(78) An OLED was produced in the same manner as in Comparative Example 1, except that compound C1-61 was used as a host.

Device Examples 2 to 5: Producing a Red Light-Emitting OLED Comprising a Compound According to the Present Disclosure

(79) OLEDs were produced in the same manner as in Comparative Example 1, except that compound HT-2 instead of compound HT-3 was used in the second hole transport layer, and the compound as shown in Table 1 below was used as a host.

(80) The measurement results of the driving voltage based on 50 mA/cm.sup.2 of the OLED produced by Comparative Example 1 and Device Examples 1 to 5 are shown in Table 1 below.

(81) TABLE-US-00011 TABLE 1 Second Hole Driving Driving Voltage Reduction Transport Voltage Rate Compared to Layer Host (V) Comparative Example 1 (%) Comparative HT-3 C 6.5 — Example 1 Device HT-3 C1-61 5.5 15.4 Example 1 Device HT-2 C1-61 5.4 16.9 Example 2 Device HT-2 C2-52 4.8 26.2 Example 3 Device HT-2 C1-65 4.7 27.7 Example 4 Device HT-2 C1-69 5.2 20.0 Example 5

Device Examples 6 to 10: Producing an OLED Comprising a Compound According to the Present Disclosure

(82) OLEDs were produced in the same manner as in Comparative Example 1, except that compound HT-2 was used in the second hole transport layer, the first and second hosts, not a single host, shown in Tables 2 and 3 were introduced into different cells so as to have a weight ratio of 50:50, and the dopant was deposited in a doping amount of 3 wt % based on the total amount of the hosts and the dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.

Comparative Examples 2 and 3: Producing an OLED Comprising Only a Second Host

(83) OLEDs were produced in the same manner as in Comparative Example 1, except that compound HT-2 was used in the second hole transport layer, and only the second host shown in Table 2 or 3 was used as a host.

(84) After producing OLEDs, the driving voltage and power efficiency at 5,000 nits were measured. The lifespan (T98), the time taken to be reduced from 100% to 98% of the luminance, based on a luminance of 5,000 nits of the produced OLEDs are shown in Tables 2 and 3 below.

(85) TABLE-US-00012 TABLE 2 Power Efficiency Increase Rate Compared Second to Hole Power Compar- Life- Trans- Driving Effi- ative span port First Second Voltage ciency Example (T98, Layer Host Host (V) (lm/W) 2 (%) hr) Compar- HT-2 — H-207 4.3 11.8 —  11 ative Example 2 Device HT-2 C1-4  H-207 3.8 18.9 60.2 160 Example 6 Device HT-2 C1-1  H-207 3.9 18.8 59.3 140 Example 7 Device HT-2 C2-1  H-207 3.9 18.6 57.6  42 Example 8 Device HT-2 C1-11 H-207 3.9 18.9 60.2 153 Example 9

(86) TABLE-US-00013 TABLE 3 Power Efficiency Increase Rate Compared Second to Hole Power Compar- Life- Trans- Driving Effi- ative span port First Second Voltage ciency Example (T98, Layer Host Host (V) (lm/W) 3 (%) hr) Compar- HT-2 — H-201 5.0 12.4 —  4 ative Example 3 Device HT-2 C1-13 H-201 3.8 21.1 70.2 24 Example 10

(87) From Device Examples 1 to 5 above, it is confirmed that the OLED produced by using the organic electroluminescent compound of the present disclosure as a host has a driving voltage lower by 15% or more as compared to the OLED produced by using a conventional compound as a host. From this, it can be seen that the same battery may be used longer, since the use of the organic electroluminescent compound of the present disclosure in a consumer electronic product requiring low power, in particular, a portable display such as a cellular phone, has a lower power consumption than that in the case of using a conventional compound as a host.

(88) In addition, from Device Examples 6 to 10 above, it can be seen that the OLEDs in which the organic electroluminescent compound of the present disclosure (the first host material) and the second host material of the present disclosure are codeposited, are superior in driving voltage, power efficiency, and lifespan to an OLED using only the second host material of the present disclosure.

(89) The compounds used in the Comparative Examples and Device Examples are shown in Table 4 below.

(90) TABLE-US-00014 TABLE 4 Hole Injection Layer/ Hole Transport Layer HI-1 HI-2 HT-1 HT-2 HT-3 Light- Emitting Layer C1-61 C2-52 C1-65 C1-69 0 D-39 C Light- Emitting Layer C1-4 C1-1 C2-1 C1-11 C1-13 H-207 H-201 Electron Transport Layer/ Electron Injection Layer ET-1 0 EI-1