COMPOUND, AND ORGANIC ELECTROLUMINESCENT MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
20250127041 ยท 2025-04-17
Inventors
- So-Young Jung (Gyeonggi-do, KR)
- Hyo-Jung Lee (Gyeonggi-do, KR)
- Hyun-Ju KANG (Gyeonggi-do, KR)
- Mi-Ran SEO (Gyeonggi-do, KR)
- YeJin JEON (Gyeonggi-do, KR)
- Tae-Jun Han (Gyeonggi-do, KR)
- Sang-Hee Cho (Gyeonggi-do, KR)
- Dong-Gil KIM (Gyeonggi-do, KR)
- So-Mi PARK (Gyeonggi-do, KR)
- Bitnari Kim (Gyeonggi-do, KR)
Cpc classification
H10K85/6574
ELECTRICITY
H10K85/626
ELECTRICITY
C07D405/04
CHEMISTRY; METALLURGY
C07D405/10
CHEMISTRY; METALLURGY
C07D263/64
CHEMISTRY; METALLURGY
H10K85/636
ELECTRICITY
C07D413/12
CHEMISTRY; METALLURGY
International classification
C07D413/12
CHEMISTRY; METALLURGY
C07D263/64
CHEMISTRY; METALLURGY
C07D405/04
CHEMISTRY; METALLURGY
C07D405/10
CHEMISTRY; METALLURGY
Abstract
The present disclosure relates to a compound, and an organic electroluminescent material and an organic electroluminescent device comprising the same. By comprising a compound and/or an organic electroluminescent material according to the present disclosure, an organic electroluminescent device having low driving voltage, and/or high luminous efficiency, and/or long lifespan characteristic, compared to the conventional organic electroluminescent device can be provided.
Claims
1. A compound represented by the following Formula 1: ##STR00552## wherein, X.sub.1 and Y.sub.1 each independently represent N, NR.sub.10, O, or S; provided that at least one of X.sub.1 and Y.sub.1 is N, and the other of X.sub.1 and Y.sub.1 is NR.sub.10, O, or S; R.sub.1 represents a substituted or unsubstituted (C.sub.6-C.sub.30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl; R.sub.2 to R.sub.10 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkoxy, a substituted or unsubstituted tri(C.sub.1-C.sub.30)alkylsilyl, a substituted or unsubstituted di(C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted tri(C.sub.6-C.sub.30)arylsilyl, or -L.sub.1-N(Ar.sub.3)(Ar.sub.4); at least one of R.sub.2 to R.sub.9 is -L.sub.1-N(Ar.sub.3)(Ar.sub.4), and at least one other(s) of R.sub.2 to R.sub.9 is a substituted or unsubstituted (C.sub.6-C.sub.30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl; L.sub.1 represents a single bond, a substituted or unsubstituted (C.sub.6-C.sub.30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; and Ar.sub.3 and Ar.sub.4 each independently represent a substituted or unsubstituted (C.sub.6-C.sub.30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl.
2. The compound according to claim 1, wherein the substituted alkyl, the substituted alkenyl, the substituted cycloalkyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, and the substituted triarylsilyl each independently is substituted with at least one selected from the group consisting of deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (C.sub.1-C.sub.30)alkyl; halo(C.sub.1-C.sub.30)alkyl; (C.sub.2-C.sub.30)alkenyl; (C.sub.2-C.sub.30)alkynyl; (C.sub.1-C.sub.30)alkoxy; (C.sub.1-C.sub.30)alkylthio; (C.sub.3-C.sub.30)cycloalkyl; (C.sub.3-C.sub.30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C.sub.6-C.sub.30)aryloxy; (C.sub.6-C.sub.30)arylthio; (C.sub.6-C.sub.30)aryl unsubstituted or substituted with at least one of (C.sub.1-C.sub.30)alkyl and di(C.sub.6-C.sub.30)arylamino; (3- to 30-membered)heteroaryl unsubstituted or substituted with at least one (C.sub.6-C.sub.30)aryl; tri(C.sub.1-C.sub.30)alkylsilyl; tri(C.sub.6-C.sub.30)arylsilyl; di(C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylsilyl; (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl; a fused ring of (C.sub.3-C.sub.30)aliphatic ring and (C.sub.6-C.sub.30)aromatic ring; amino; mono- or di(C.sub.1-C.sub.30)alkylamino; mono- or di(C.sub.2-C.sub.30)alkenylamino; mono- or di(C.sub.6-C.sub.30)arylamino unsubstituted or substituted with (C.sub.1-C.sub.30)alkyl; mono- or di(3- to 30-membered)heteroarylamino; (C.sub.1-C.sub.30)alkyl(C.sub.2-C.sub.30)alkenylamino; (C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylamino; (C.sub.1-C.sub.30)alkyl(3- to 30-membered)heteroarylamino; (C.sub.2-C.sub.30)alkenyl(C.sub.6-C.sub.30)arylamino; (C.sub.2-C.sub.30)alkenyl(3- to 30-membered)heteroarylamino; (C.sub.6-C.sub.30)aryl(3- to 30-membered)heteroarylamino; (C.sub.1-C.sub.30)alkylcarbonyl; (C.sub.1-C.sub.30)alkoxycarbonyl; (C.sub.6-C.sub.30)arylcarbonyl; di(C.sub.6-C.sub.30)arylboronyl; di(C.sub.1-C.sub.30)alkylboronyl; (C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylboronyl; (C.sub.6-C.sub.30)ar(C.sub.1-C.sub.30)alkyl; and (C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)aryl.
3. The compound according to claim 1, wherein the compound represented by Formula 1 is selected from the following compounds: ##STR00553## ##STR00554## ##STR00555## ##STR00556## ##STR00557## ##STR00558## ##STR00559## ##STR00560## ##STR00561## ##STR00562## ##STR00563## ##STR00564## ##STR00565## ##STR00566## ##STR00567## ##STR00568## ##STR00569## ##STR00570## ##STR00571## ##STR00572## ##STR00573## ##STR00574## ##STR00575## ##STR00576## ##STR00577## ##STR00578## ##STR00579## ##STR00580## ##STR00581## ##STR00582## ##STR00583## ##STR00584## ##STR00585## ##STR00586## ##STR00587## ##STR00588## ##STR00589## ##STR00590## ##STR00591## ##STR00592## ##STR00593## ##STR00594## ##STR00595## ##STR00596## ##STR00597## ##STR00598## ##STR00599## ##STR00600## ##STR00601## ##STR00602## ##STR00603## ##STR00604## ##STR00605## ##STR00606## ##STR00607## ##STR00608## ##STR00609## ##STR00610## ##STR00611## ##STR00612## ##STR00613## ##STR00614## ##STR00615## ##STR00616## ##STR00617## ##STR00618## ##STR00619## ##STR00620## ##STR00621## ##STR00622## ##STR00623## ##STR00624## ##STR00625##
4. An organic electroluminescent material comprising the compound represented by Formula 1 according to claim 1, and a compound represented by the following Formula 2: ##STR00626## wherein, Z.sub.1 to Z.sub.3 each independently represent N or C(R.sub.20); provided that at least one of Z.sub.1 to Z.sub.3 is N; R.sub.20 represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkoxy, a substituted or unsubstituted tri(C.sub.1-C.sub.30)alkylsilyl, a substituted or unsubstituted di(C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted tri(C.sub.6-C.sub.30)arylsilyl, or a substituted or unsubstituted fused ring of (C.sub.3-C.sub.30)aliphatic ring and (C.sub.6-C.sub.30)aromatic ring; L.sub.2 to L.sub.4 each independently represent a single bond, a substituted or unsubstituted (C.sub.6-C.sub.30)arylene, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; Ar.sub.5 to Ar.sub.7 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkoxy, a substituted or unsubstituted tri(C.sub.1-C.sub.30)alkylsilyl, a substituted or unsubstituted di(C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted tri(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted fused ring of (C.sub.3-C.sub.30)aliphatic ring and (C.sub.6-C.sub.30)aromatic ring, or *N(R.sub.11)(R.sub.12); or may be linked to the adjacent substituents to form a ring(s); provided that at least one of Ar.sub.5 to Ar.sub.7 is a substituted or unsubstituted (C.sub.6-C.sub.30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl; and R.sub.11 and R.sub.12 each independently represent a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl.
5. The organic electroluminescent material according to claim 4, wherein at least one of Ar.sub.5 to Ar.sub.7 is represented by any one of the following Formulas 2-1 to 2-7. ##STR00627## wherein, Y represents O, S, N(R.sub.77), or C(R.sub.78)(R.sub.79); R.sub.77 represents a site connected to any one of L.sub.2 to L.sub.4, or a substituted or unsubstituted (C.sub.6-C.sub.30)aryl; R.sub.78 and R.sub.79 each independently represent a site connected to any one of L.sub.2 to L.sub.4, or a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or R.sub.78 and R.sub.79 can be connected to each other to form a ring(s); R.sub.21 to R.sub.28, R.sub.30 to R.sub.57, and R.sub.59 to R.sub.64 each independently represent a site connected to any one of L.sub.2 to L.sub.4; or hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkoxy, a substituted or unsubstituted tri(C.sub.1-C.sub.30)alkylsilyl, a substituted or unsubstituted di(C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted tri(C.sub.6-C.sub.30)arylsilyl, or a substituted or unsubstituted fused ring of (C.sub.3-C.sub.30)aliphatic ring and (C.sub.6-C.sub.30)aromatic ring; or may be linked to the adjacent substituents to form a ring(s); X.sub.3 to X.sub.6 each independently represent O, S, Se, or N; and R.sub.29 and R.sub.58 each independently represent a site connected to any one of L.sub.2 to L.sub.4, or a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl.
6. The organic electroluminescent material according to claim 4, wherein the substituted alkyl, the substituted alkenyl, the substituted cycloalkyl(ene), the substituted aryl(ene), the substituted heteroaryl(ene), the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, and the substituted fused ring of aliphatic ring and aromatic ring each independently is substituted with at least one selected from the group consisting of deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (C.sub.1-C.sub.30)alkyl; halo(C.sub.1-C.sub.30)alkyl; (C.sub.2-C.sub.30)alkenyl; (C.sub.2-C.sub.30)alkynyl; (C.sub.1-C.sub.30)alkoxy; (C.sub.1-C.sub.30)alkylthio; (C.sub.3-C.sub.30)cycloalkyl; (C.sub.3-C.sub.30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C.sub.6-C.sub.30)aryloxy; (C.sub.6-C.sub.30)arylthio; (C.sub.6-C.sub.30)aryl unsubstituted or substituted with at least one of (C.sub.1-C.sub.30)alkyl and di(C.sub.6-C.sub.30)arylamino; (3- to 30-membered)heteroaryl unsubstituted or substituted with at least one (C.sub.6-C.sub.30)aryl; tri(C.sub.1-C.sub.30)alkylsilyl; tri(C.sub.6-C.sub.30)arylsilyl; di(C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylsilyl; (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl; a fused ring of (C.sub.3-C.sub.30)aliphatic ring and (C.sub.6-C.sub.30)aromatic ring; amino; mono- or di(C.sub.1-C.sub.30)alkylamino; mono- or di(C.sub.2-C.sub.30)alkenylamino; mono- or di(C.sub.6-C.sub.30)arylamino unsubstituted or substituted with (C.sub.1-C.sub.30)alkyl; mono- or di(3- to 30-membered)heteroarylamino; (C.sub.1-C.sub.30)alkyl(C.sub.2-C.sub.30)alkenylamino; (C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylamino; (C.sub.1-C.sub.30)alkyl(3- to 30-membered)heteroarylamino; (C.sub.2-C.sub.30)alkenyl(C.sub.6-C.sub.30)arylamino; (C.sub.2-C.sub.30)alkenyl(3- to 30-membered)heteroarylamino; (C.sub.6-C.sub.30)aryl(3- to 30-membered)heteroarylamino; (C.sub.1-C.sub.30)alkylcarbonyl; (C.sub.1-C.sub.30)alkoxycarbonyl; (C.sub.6-C.sub.30)arylcarbonyl; di(C.sub.6-C.sub.30)arylboronyl; di(C.sub.1-C.sub.30)alkylboronyl; (C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylboronyl; (C.sub.6-C.sub.30)ar(C.sub.1-C.sub.30)alkyl; and (C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)aryl.
7. The organic electroluminescent material according to claim 4, wherein the compound represented by Formula 2 is selected from the following compounds: ##STR00628## ##STR00629## ##STR00630## ##STR00631## ##STR00632## ##STR00633## ##STR00634## ##STR00635## ##STR00636## ##STR00637## ##STR00638## ##STR00639## ##STR00640## ##STR00641## ##STR00642## ##STR00643## ##STR00644## ##STR00645## ##STR00646## ##STR00647## ##STR00648## ##STR00649## ##STR00650## ##STR00651## ##STR00652## ##STR00653## ##STR00654## ##STR00655## ##STR00656## ##STR00657## ##STR00658## ##STR00659## ##STR00660## ##STR00661## ##STR00662## ##STR00663## ##STR00664## ##STR00665## ##STR00666## ##STR00667## ##STR00668## ##STR00669## ##STR00670## ##STR00671## ##STR00672## ##STR00673## ##STR00674## ##STR00675## ##STR00676## ##STR00677## ##STR00678## ##STR00679## ##STR00680## ##STR00681## ##STR00682## ##STR00683## ##STR00684## ##STR00685## ##STR00686## ##STR00687## ##STR00688## ##STR00689## ##STR00690## ##STR00691## ##STR00692## ##STR00693## ##STR00694## ##STR00695## ##STR00696## ##STR00697## ##STR00698## ##STR00699## ##STR00700## ##STR00701## ##STR00702## ##STR00703## ##STR00704## ##STR00705## ##STR00706## ##STR00707## ##STR00708## ##STR00709## ##STR00710## ##STR00711## ##STR00712## ##STR00713## ##STR00714## ##STR00715## ##STR00716## ##STR00717## ##STR00718## ##STR00719## ##STR00720## ##STR00721## ##STR00722## ##STR00723## ##STR00724## ##STR00725## ##STR00726## ##STR00727## ##STR00728## ##STR00729## ##STR00730## ##STR00731## ##STR00732## ##STR00733## ##STR00734## ##STR00735## ##STR00736## ##STR00737## ##STR00738## ##STR00739## ##STR00740## ##STR00741## ##STR00742## ##STR00743## ##STR00744## ##STR00745## ##STR00746## ##STR00747## ##STR00748## ##STR00749## ##STR00750## ##STR00751## ##STR00752## ##STR00753## ##STR00754## ##STR00755## ##STR00756## ##STR00757## ##STR00758## ##STR00759## ##STR00760## ##STR00761## ##STR00762## ##STR00763## ##STR00764## ##STR00765## ##STR00766## ##STR00767## ##STR00768## ##STR00769## ##STR00770## ##STR00771## ##STR00772## ##STR00773## ##STR00774## ##STR00775## ##STR00776## ##STR00777## ##STR00778## ##STR00779## ##STR00780## ##STR00781## ##STR00782## ##STR00783## ##STR00784## ##STR00785## ##STR00786## ##STR00787## ##STR00788## ##STR00789## ##STR00790## ##STR00791## ##STR00792## ##STR00793## ##STR00794## ##STR00795## ##STR00796## ##STR00797## ##STR00798## ##STR00799## ##STR00800## ##STR00801## ##STR00802## ##STR00803## ##STR00804## ##STR00805## ##STR00806## ##STR00807## ##STR00808## ##STR00809## ##STR00810## ##STR00811## ##STR00812## ##STR00813## ##STR00814## ##STR00815## ##STR00816## ##STR00817## ##STR00818## ##STR00819## ##STR00820## ##STR00821## ##STR00822## ##STR00823## ##STR00824## ##STR00825## ##STR00826## ##STR00827## ##STR00828## ##STR00829## ##STR00830## ##STR00831## ##STR00832## ##STR00833## ##STR00834## ##STR00835## ##STR00836## ##STR00837## ##STR00838## ##STR00839## ##STR00840## ##STR00841## ##STR00842## ##STR00843## ##STR00844## ##STR00845## ##STR00846## ##STR00847## ##STR00848## ##STR00849## ##STR00850## ##STR00851## ##STR00852## ##STR00853## ##STR00854## ##STR00855## ##STR00856## ##STR00857## ##STR00858## ##STR00859## ##STR00860## ##STR00861## ##STR00862## ##STR00863## ##STR00864## ##STR00865## ##STR00866## ##STR00867## ##STR00868## ##STR00869## ##STR00870## ##STR00871## ##STR00872## ##STR00873## ##STR00874## ##STR00875## ##STR00876## ##STR00877## ##STR00878## ##STR00879## ##STR00880## ##STR00881## ##STR00882## ##STR00883## ##STR00884## ##STR00885## ##STR00886## ##STR00887## ##STR00888## ##STR00889## ##STR00890## ##STR00891## ##STR00892## ##STR00893## ##STR00894## ##STR00895## ##STR00896## ##STR00897## ##STR00898## ##STR00899## ##STR00900## ##STR00901## ##STR00902## ##STR00903## ##STR00904## ##STR00905## ##STR00906## ##STR00907## ##STR00908## ##STR00909## ##STR00910## ##STR00911## ##STR00912## ##STR00913## ##STR00914## ##STR00915## ##STR00916## ##STR00917## ##STR00918## ##STR00919## ##STR00920## ##STR00921## ##STR00922## ##STR00923## ##STR00924## ##STR00925## ##STR00926## ##STR00927## ##STR00928## ##STR00929## ##STR00930## ##STR00931## ##STR00932## ##STR00933## ##STR00934## ##STR00935## ##STR00936## ##STR00937## ##STR00938## ##STR00939## ##STR00940## ##STR00941## ##STR00942## ##STR00943## ##STR00944## ##STR00945## ##STR00946## ##STR00947## ##STR00948## ##STR00949## ##STR00950## ##STR00951## ##STR00952## ##STR00953## ##STR00954## ##STR00955## ##STR00956## ##STR00957## ##STR00958## ##STR00959## ##STR00960## ##STR00961## ##STR00962## ##STR00963## ##STR00964## ##STR00965## ##STR00966## ##STR00967## ##STR00968## ##STR00969## ##STR00970## ##STR00971## ##STR00972## ##STR00973## ##STR00974## ##STR00975## ##STR00976## ##STR00977## ##STR00978## ##STR00979## ##STR00980## ##STR00981## ##STR00982## ##STR00983## ##STR00984## ##STR00985## ##STR00986## ##STR00987## ##STR00988## ##STR00989## ##STR00990## ##STR00991## ##STR00992## ##STR00993## ##STR00994## ##STR00995## ##STR00996## ##STR00997## ##STR00998## ##STR00999## ##STR01000## ##STR01001## ##STR01002## ##STR01003## ##STR01004## ##STR01005## ##STR01006## ##STR01007## ##STR01008## ##STR01009## ##STR01010## ##STR01011## ##STR01012## ##STR01013## ##STR01014## ##STR01015## ##STR01016## ##STR01017## ##STR01018## ##STR01019## ##STR01020## ##STR01021## ##STR01022## ##STR01023## ##STR01024## ##STR01025## ##STR01026## ##STR01027## ##STR01028## ##STR01029## ##STR01030## ##STR01031## ##STR01032## ##STR01033## ##STR01034## ##STR01035## ##STR01036## ##STR01037## ##STR01038## ##STR01039## ##STR01040## ##STR01041## ##STR01042## ##STR01043##
8. An organic electroluminescent device comprising the compound according to claim 1.
9. An organic electroluminescent device comprising the organic electroluminescent material according to claim 4.
10. An organic electroluminescent device comprising the organic electroluminescent material according to claim 4, wherein the organic electroluminescent device comprises a first compound represented by Formula 1 and a second compound represented by Formula 2, and further comprises a third compound which is selected from the compounds represented by Formulas 1 and 2 and is different from the first compound and the second compound.
11. A compound represented by the following Formula 2-1-1: ##STR01044## wherein, L.sub.2 and L.sub.3 each independently represent a single bond, a substituted or unsubstituted (C.sub.6-C.sub.30)arylene, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; Ar.sub.5 is represented by the following Formula 2-1; ##STR01045## wherein, Y represents O or S; R.sub.21 to R.sub.28 each independently represent a site connected to L.sub.2; or hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkoxy, a substituted or unsubstituted tri(C.sub.1-C.sub.30)alkylsilyl, a substituted or unsubstituted di(C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted tri(C.sub.6-C.sub.30)arylsilyl, or a substituted or unsubstituted fused ring of (C.sub.3-C.sub.30)aliphatic ring and (C.sub.6-C.sub.30)aromatic ring; or may be linked to the adjacent substituents to form a ring(s); Ar.sub.6 represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkoxy, a substituted or unsubstituted tri(C.sub.1-C.sub.30)alkylsilyl, a substituted or unsubstituted di(C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted tri(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted fused ring of (C.sub.3-C.sub.30)aliphatic ring and (C.sub.6-C.sub.30)aromatic ring; or may be linked to the adjacent substituents to form a ring(s); L.sub.4 represents phenylene unsubstituted or substituted with deuterium or cyano, biphenylene unsubstituted or substituted with deuterium or cyano, or 2-naphthylene unsubstituted or substituted with deuterium or cyano; Ar.sub.7 represents biphenyl unsubstituted or substituted with deuterium or cyano, naphthyl unsubstituted or substituted with deuterium or cyano, or phenylnaphthyl unsubstituted or substituted with deuterium or cyano; Provided that when L.sub.4 is phenylene unsubstituted or substituted with deuterium or cyano, Ar.sub.7 is biphenyl unsubstituted or substituted with deuterium or cyano or naphthyl unsubstituted or substituted with deuterium or cyano; When L.sub.4 is biphenylene unsubstituted or substituted with deuterium or cyano, Ar.sub.7 is naphthyl unsubstituted or substituted with deuterium or cyano; When L.sub.4 is 2-naphthylene unsubstituted or substituted with deuterium or cyano, Ar.sub.7 is biphenyl unsubstituted or substituted with deuterium or cyano, or phenylnaphthyl unsubstituted or substituted with deuterium or cyano.
12. The compound according to claim 11, wherein the compound represented by Formula 2-1-1 is selected from the following compounds: ##STR01046## ##STR01047## ##STR01048## ##STR01049## ##STR01050## ##STR01051## ##STR01052## ##STR01053## ##STR01054## ##STR01055## ##STR01056## ##STR01057## ##STR01058##
13. A compound represented by the following Formula 2-1-2: ##STR01059## wherein, L.sub.2 and L.sub.3 each independently represent a single bond, a substituted or unsubstituted (C.sub.6-C.sub.30)arylene, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; Ar.sub.5 is represented by the following Formula 2-1; ##STR01060## wherein, Y represents O or S; R.sub.21 to R.sub.28 each independently represent a site connected to L.sub.2; or hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkoxy, a substituted or unsubstituted tri(C.sub.1-C.sub.30)alkylsilyl, a substituted or unsubstituted di(C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted tri(C.sub.6-C.sub.30)arylsilyl, or a substituted or unsubstituted fused ring of (C.sub.3-C.sub.30)aliphatic ring and (C.sub.6-C.sub.30)aromatic ring; or may be linked to the adjacent substituents to form a ring(s); Ar.sub.6 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkoxy, a substituted or unsubstituted tri(C.sub.1-C.sub.30)alkylsilyl, a substituted or unsubstituted di(C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted tri(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted fused ring of (C.sub.3-C.sub.30)aliphatic ring and (C.sub.6-C.sub.30)aromatic ring; or may be linked to the adjacent substituents to form a ring(s); L.sub.4 represents 1-naphthylene selected from the following Group 2 unsubstituted or substituted with deuterium or cyano: ##STR01061## in Group 2, * represents points connected to Formula 2-1-2 and Ar.sub.7; and Ar.sub.7 represents (C.sub.6-C.sub.16)aryl unsubstituted or substituted with deuterium.
14. The compound according to claim 13, wherein the compound represented by Formula 2-1-2 is selected from the following compounds: ##STR01062## ##STR01063## ##STR01064## ##STR01065## ##STR01066## ##STR01067## ##STR01068## ##STR01069## ##STR01070## ##STR01071## ##STR01072## ##STR01073## ##STR01074## ##STR01075## ##STR01076## ##STR01077## ##STR01078## ##STR01079## ##STR01080## ##STR01081##
15. An organic electroluminescent device comprising the compound according to claim 11.
16. An organic electroluminescent device comprising the compound according to claim 13.
Description
MODE FOR THE INVENTION
[0020] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the invention, and is not meant in any way to restrict the scope of the invention.
[0021] The present disclosure relates to a compound represented by Formula 1 above, an organic electroluminescent material comprising the compound, and an organic electroluminescent device comprising the organic electroluminescent material.
[0022] The organic electroluminescent material according to the present disclosure includes a compound represented by Formula 1 and a compound represented by Formula 2.
[0023] The present disclosure relates to a compound represented by Formula 2-1-1 and an organic electroluminescent device comprising the same.
[0024] The present disclosure relates to a compound represented by Formula 2-1-2 and an organic electroluminescent device comprising the same.
[0025] The term organic electroluminescent compound in the present disclosure means a compound that may be used in an organic electroluminescent device, and may be comprised in any material layer constituting an organic electroluminescent device, as necessary.
[0026] Herein, organic electroluminescent material means a material that may be used in an organic electroluminescent device, and may comprise at least one compound. The organic electroluminescent material may be comprised in any layer constituting an organic electroluminescent device, as necessary. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron-blocking material, a light-emitting material (containing host and dopant materials), an electron buffer material, a hole-blocking material, an electron transport material, or an electron injection material, etc.
[0027] The term a plurality of organic electroluminescent materials in the present disclosure means an organic electroluminescent material comprising a combination of at least two compounds, which may be comprised in any layer constituting an organic electroluminescent device. It may mean both a material before being comprised in an organic electroluminescent device (for example, before vapor deposition) and a material after being comprised in an organic electroluminescent device (for example, after vapor deposition). For example, a plurality of organic electroluminescent materials may be a combination of at least two compounds, which may be comprised in at least one layer of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron-blocking layer, a light-emitting layer, an electron buffer layer, a hole-blocking layer, an electron transport layer, and an electron injection layer. Such at least two compounds may be comprised in the same layer or different layers, and may be mixture-evaporated or co-evaporated, or may be individually evaporated.
[0028] Herein, a plurality of host materials means an organic electroluminescent material comprising a combination of at least two host materials. It may mean both a material before being comprised in an organic electroluminescent device (e.g., before vapor deposition) and a material after being comprised in an organic electroluminescent device (e.g., after vapor deposition). A plurality of host materials of the present disclosure may be comprised in any light-emitting layer constituting an organic electroluminescent device. The at least two compounds comprised in a plurality of host materials may be comprised together in one light-emitting layer, or may each be comprised in separate light-emitting layers. When at least two compounds are comprised in one light-emitting layer, the at least two compounds may be mixture-evaporated to form a layer or may be individually and simultaneously co-evaporated to form a layer.
[0029] Herein, (C.sub.1-C.sub.30)alkyl(ene) is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. Herein, the (C.sub.3-C.sub.30)cycloalkyl(ene) is meant to be a mono- or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, in which the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. Herein, (C.sub.6-C.sub.30)aryl(ene) is a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, in which the number of the ring backbone carbon atoms is preferably 6 to 20, more preferably 6 to 15, may be partially saturated, and may include a spiro structure. Examples of the aryl specifically may be phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluoren-fluoren]yl, spiro[fluoren-benzofluoren]yl, azulenyl, tetramethyl-dihydrophenanthrenyl, etc. More specifically, the aryl may be o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-t-butylphenyl, p-(2-phenylpropyl)phenyl, 4-methylbiphenyl, 4-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthrenyl, etc. Herein, (3- to 30-membered)heteroaryl(ene) is an aryl having 3 to 30 ring backbone atoms and including at least one, preferably 1 to 4 heteroatom(s) selected from the group consisting of B, N, O, S, Si, P, Se, and Ge, in which the number of the ring backbone carbon atoms is preferably 5 to 25. The above heteroaryl(ene) may be a monocyclic ring, or a fused ring condensed with at least one benzene ring, and may be partially saturated. Also, the above heteroaryl herein may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s). Examples of the heteroaryl specifically may be a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthiridinyl, benzofuropyrimidinyl, naphthofuropyrimidinyl, benzothienoquinolinyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidoindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolizidinyl, acridinyl, silafluorenyl, germafluorenyl, benzotriazolyl, phenazinyl, imidazopyridinyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzopyrimidinyl, indolocarbazolyl, indenocarbazolyl, etc. More specifically, the heteroaryl may be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-indolizidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazol-1-yl, azacarbazol-2-yl, azacarbazol-3-yl, azacarbazol-4-yl, azacarbazol-5-yl, azacarbazol-6-yl, azacarbazol-7-yl, azacarbazol-8-yl, azacarbazol-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-t-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1,2-b]-benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl, 2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2,3-b]-benzothiophenyl, 4-naphtho-[2,3-b]-benzothiophenyl, 5-naphtho-[2,3-b]-benzothiophenyl, 1-naphtho-[2,1-b]-benzothiophenyl, 2-naphtho-[2,1-b]-benzothiophenyl, 3-naphtho-[2,1-b]-benzothiophenyl, 4-naphtho-[2,1-b]-benzothiophenyl, 5-naphtho-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl, 7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzofuro[3,2-d]pyrimidinyl, 6-benzofuro[3,2-d]pyrimidinyl, 7-benzofuro[3,2-d]pyrimidinyl, 8-benzofuro[3,2-d]pyrimidinyl, 9-benzofuro[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl, 6-benzothio[3,2-d]pyrimidinyl, 7-benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9-benzothio[3,2-d]pyrimidinyl, 2-benzofuro[3,2-d]pyrazinyl, 6-benzofuro[3,2-d]pyrazinyl, 7-benzofuro[3,2-d]pyrazinyl, 8-benzofuro[3,2-d]pyrazinyl, 9-benzofuro[3,2-d]pyrazinyl, 2-benzothio[3,2-d]pyrazinyl, 6-benzothio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d]pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. Additionally, heteroaryl(ene) can be classified into a heteroaryl(ene) with electronic properties and a heteroaryl(ene) with hole properties. A heteroaryl(ene) with electronic properties is a substituent with relatively abundant electrons in the parent nucleus, and for example, it may be a substituted or unsubstituted pyridinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted quinolyl, etc. A heteroaryl(ene), which has hole properties, is a substituent with a relative lack of electrons in the parent nucleus, and for example, it may be a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl. Herein, the term a fused ring of (C.sub.3-C.sub.30)aliphatic ring and (C.sub.6-C.sub.30)aromatic ring means a ring formed by fusing at least one aliphatic ring having 3 to 30 ring backbone carbon atoms in which the number of carbon atoms is preferably 3 to 25, more preferably 3 to 18, and at least one aromatic ring having 6 to 30 ring backbone carbon atoms in which the number of carbon atoms is preferably 6 to 25, more preferably 6 to 18. For example, the fused ring may be a fused ring of at least one benzene and at least one cyclohexane, or a fused ring of at least one naphthalene and at least one cyclopentane, etc. Herein, the carbon atoms in the fused ring of (C.sub.3-C.sub.30)aliphatic ring and (C.sub.6-C.sub.30)aromatic ring may be replaced with at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. The halogen in the present disclosure includes F, Cl, Br, and I.
[0030] In addition, ortho- (o-), meta- (m-), and para- (p-) are meant to signify the substitution position of all substituents. An ortho-configuration describes a compound with substituents which are adjacent to each other, e.g., at the 1 and 2 positions on benzene. A meta-configuration indicates the next substitution position of the immediately adjacent substitution position, e.g., a compound with substituents at the 1 and 3 positions on benzene. A para-configuration indicates the next substitution position from the meta-position, e.g., a compound with substituents at the 1 and 4 positions on benzene.
[0031] Herein, the term a ring formed in linking to an adjacent substituent means a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof, formed by linking or fusing two or more adjacent substituents, and preferably this may be a substituted or unsubstituted (3- to 26-membered) mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof. Further, the formed ring may include at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably N, O, and S. According to one embodiment of the present disclosure, the number of atoms in the ring skeleton is 5 to 20; according to another embodiment of the present disclosure, the number of atoms in the ring skeleton is 5 to 15. In one embodiment, the fused ring may be, for example, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted carbazole ring, etc.
[0032] In addition, substituted in the expression substituted or unsubstituted means that a hydrogen atom in a certain functional group is replaced with another atom or functional group, i.e., a substituent. Unless otherwise specified, the substituents may not be limited to hydrogen at positions where the substituents may be substituted, and when two or more hydrogen atoms are each replaced with a substituent in a functional group, the substituents may be the same or different from each other. For example, a substituent to which two or more substituents are connected may be pyridine-triazine. That is, pyridine-triazine may be heteroaryl or may be interpreted as one substituent in which two heteroaryls are connected. The substituents of the substituted alkyl, the substituted alkenyl, the substituted cycloalkyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, and the substituted fused ring of aliphatic ring and aromatic ring in the formulas of the present disclosure, each independently represent at least one selected from the group consisting of deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; (C.sub.1-C.sub.30)alkyl; halo(C.sub.1-C.sub.30)alkyl; (C.sub.2-C.sub.30)alkenyl; (C.sub.2-C.sub.30)alkynyl; (C.sub.1-C.sub.30)alkoxy; (C.sub.1-C.sub.30)alkylthio; (C.sub.3-C.sub.30)cycloalkyl; (C.sub.3-C.sub.30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C.sub.6-C.sub.30)aryloxy; (C.sub.6-C.sub.30)arylthio; (3- to 30-membered)heteroaryl unsubstituted or substituted with at least one (C.sub.6-C.sub.30)aryl; (C.sub.6-C.sub.30)aryl unsubstituted or substituted with at least one of (C.sub.1-C.sub.30)alkyl and (3- to 30-membered)heteroaryl; tri(C.sub.1-C.sub.30)alkylsilyl; tri(C.sub.6-C.sub.30)arylsilyl; di(C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylsilyl; (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl; tri(C.sub.6-C.sub.30)arylgermanyl; amino; mono- or di(C.sub.1-C.sub.30)alkylamino; mono- or di(C.sub.2-C.sub.30)alkenylamino; mono- or di(C.sub.6-C.sub.30)arylamino unsubstituted or substituted with (C.sub.1-C.sub.30)alkyl; mono- or di(3- to 30-membered)heteroarylamino; (C.sub.1-C.sub.30)alkyl(C.sub.2-C.sub.30)alkenylamino; (C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylamino; (C.sub.1-C.sub.30)alkyl(3- to 30-membered)heteroarylamino; (C.sub.2-C.sub.30)alkenyl(C.sub.6-C.sub.30)arylamino; (C.sub.2-C.sub.30)alkenyl(3- to 30-membered)heteroarylamino; (C.sub.6-C.sub.30)aryl(3- to 30-membered)heteroarylamino; (C.sub.1-C.sub.30)alkylcarbonyl; (C.sub.1-C.sub.30)alkoxycarbonyl; (C.sub.6-C.sub.30)arylcarbonyl; di(C.sub.6-C.sub.30)arylboronyl; di(C.sub.1-C.sub.30)alkylboronyl; (C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylboronyl; (C.sub.6-C.sub.30)ar(C.sub.1-C.sub.30)alkyl; and (C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)aryl, etc. For example, the substituents in the substituted groups may be phenyl, naphthyl, pyridyl, dibenzofuranyl, or dibenzothiophenyl, etc.
[0033] Herein, combinations thereof signifies that one or more components of the corresponding list are combined to form a known or chemically stable arrangement that a person skilled in the art could conceive of from the corresponding list. For example, alkyl and deuterium may be combined to form partially or entirely deuterated alkyl groups; halogen and alkyl may be combined to form halogenated alkyl substituents; and halogen, alkyl, and aryl may be combined to form halogenated arylalkyl. For example, preferred combinations of substituents may include up to 50 atoms excluding hydrogen and deuterium, or include up to 40 atoms excluding hydrogen and deuterium, or include up to 30 atoms excluding hydrogen and deuterium, or in many cases, preferred combinations of substituents may include up to 20 atoms excluding hydrogen and deuterium.
[0034] In the formula of the present disclosure, when multiple substituents are indicated by the same symbol, each of these substituents represented by the same symbol may be the identical or different from one another.
[0035] Hereinafter, the compound according to one embodiment will be described.
[0036] The compound according to one embodiment is represented by the following Formula 1.
##STR00003## [0037] In Formula 1, [0038] X.sub.1 and Y.sub.1 each independently represent N, NR.sub.10, O, or S; provided that at least one of X.sub.1 and Y.sub.1 is N, and the other of X.sub.1 and Y.sub.1 is NR.sub.10, O, or S; [0039] R.sub.1 represents a substituted or unsubstituted (C.sub.6-C.sub.30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl; [0040] R.sub.2 to R.sub.10 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkoxy, a substituted or unsubstituted tri(C.sub.1-C.sub.30)alkylsilyl, a substituted or unsubstituted di(C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted tri(C.sub.6-C.sub.30)arylsilyl, or -L.sub.1-N(Ar.sub.3)(Ar.sub.4); [0041] at least one of R.sub.2 to R.sub.9 is -L.sub.1-N(Ar.sub.3)(Ar.sub.4), and at least one other(s) of R.sub.2 to R.sub.9 is a substituted or unsubstituted (C.sub.6-C.sub.30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl; [0042] L.sub.1 represents a single bond, a substituted or unsubstituted (C.sub.6-C.sub.30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; and [0043] Ar.sub.3 and Ar.sub.4 each independently represent a substituted or unsubstituted (C.sub.6-C.sub.30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl.
[0044] In one embodiment, at least one of X.sub.1 and Y.sub.1 may be N, and the other of X.sub.1 and Y.sub.1 may be O or S.
[0045] In one embodiment, R.sub.5 may be -L.sub.1-N(Ar.sub.3)(Ar.sub.4), and R.sub.7 or R.sub.8 may be a substituted or unsubstituted (C.sub.6-C.sub.30)aryl or a substituted or unsubstituted (5- to 30-membered)heteroaryl.
[0046] In one embodiment, R.sub.7 may be -L.sub.1-N(Ar.sub.3)(Ar.sub.4), and R.sub.5 may be a substituted or unsubstituted (C.sub.6-C.sub.30)aryl or a substituted or unsubstituted (5- to 30-membered)heteroaryl.
[0047] In one embodiment, R.sub.8 may be -L.sub.1-N(Ar.sub.3)(Ar.sub.4), and R.sub.4 or R.sub.5 may be a substituted or unsubstituted (C.sub.6-C.sub.30)aryl or a substituted or unsubstituted (5- to 30-membered)heteroaryl.
[0048] In one embodiment, R.sub.1 may be a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, for example, it may be a substituted or unsubstituted phenyl.
[0049] In one embodiment, at least one of R.sub.2 to R.sub.9 may be -L.sub.1-N(Ar.sub.3)(Ar.sub.4), and at least one other(s) of R.sub.2 to R.sub.9 may be a substituted or unsubstituted (C.sub.6-C.sub.30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl.
[0050] In one embodiment, the other of R.sub.2 to R.sub.9 that is not -L.sub.1-N(Ar.sub.3)(Ar.sub.4) may be a substituted or unsubstituted (C.sub.6-C.sub.30)aryl or a substituted or unsubstituted (5- to 30-membered)heteroaryl, preferably a substituted or unsubstituted (C.sub.6-C.sub.25)aryl or a substituted or unsubstituted (5- to 25-membered)heteroaryl, more preferably a substituted or unsubstituted (C.sub.6-C.sub.18)aryl or a substituted or unsubstituted (5- to 18-membered)heteroaryl, for example, phenyl unsubstituted or substituted with pyridyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted m-biphenyl, pyridyl unsubstituted or substituted with phenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl.
[0051] In one embodiment, L.sub.1 may be a single bond or a substituted or unsubstituted (C.sub.6-C.sub.30)arylene, preferably a single bond or a substituted or unsubstituted (C.sub.6-C.sub.25)arylene, more preferably a single bond or a substituted or unsubstituted (C.sub.6-C.sub.18)arylene. For example, L.sub.1 may be a single bond or a substituted or unsubstituted phenylene.
[0052] In one embodiment, Ar.sub.3 and Ar.sub.4 each independently may be, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl or a substituted or unsubstituted (5- to 30-membered)heteroaryl, preferably a substituted or unsubstituted (C.sub.6-C.sub.25)aryl or a substituted or unsubstituted (5- to 25-membered)heteroaryl, more preferably (C.sub.6-C.sub.18)aryl unsubstituted or substituted with (C.sub.6-C.sub.30)aryl or (5- to 30-membered)heteroaryl or a substituted or unsubstituted (5- to 18-membered)heteroaryl. For example, Ar.sub.3 and Ar.sub.4 each independently may be phenyl unsubstituted or substituted with at least one of naphthyl, phenanthrenyl, dibenzofuranyl, and dibenzothiophenyl, naphthyl unsubstituted or substituted with phenyl, a substituted or unsubstituted o-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted p-terphenyl, phenanthrenyl unsubstituted or substituted with phenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted dibenzoselenophenyl, or carbazolyl unsubstituted or substituted with phenyl or biphenyl.
[0053] According to one embodiment, the compound represented by Formula 1 may be more specifically illustrated by the following compounds, but is not limited thereto.
##STR00004## ##STR00005## ##STR00006## ##STR00007## ##STR00008## ##STR00009## ##STR00010## ##STR00011## ##STR00012## ##STR00013## ##STR00014## ##STR00015## ##STR00016## ##STR00017## ##STR00018## ##STR00019## ##STR00020##
##STR00021## ##STR00022## ##STR00023## ##STR00024## ##STR00025## ##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036## ##STR00037## ##STR00038## ##STR00039## ##STR00040## ##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065## ##STR00066## ##STR00067## ##STR00068## ##STR00069## ##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083##
[0054] The compound represented by Formula 1 according to the present disclosure can be manufactured by referring to a synthesis method known to those skilled in the art, for example, the synthesis method disclosed in Korean Patent Application Laid-open Nos. 2017-0022865, 2018-0099487, etc., but is not limited thereto.
[0055] According to another embodiment of the present disclosure, the present disclosure provides an organic electroluminescent material comprising the compound represented by Formula 1 and a compound represented by the following Formula 2.
##STR00084## [0056] In Formula 2, [0057] Z.sub.1 to Z.sub.3 each independently represent N or C(R.sub.20); provided that at least one of Z.sub.1 to Z.sub.3 is N; [0058] R.sub.20 represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkoxy, a substituted or unsubstituted tri(C.sub.1-C.sub.30)alkylsilyl, a substituted or unsubstituted di(C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted tri(C.sub.6-C.sub.30)arylsilyl, or a substituted or unsubstituted fused ring of (C.sub.3-C.sub.30)aliphatic ring and (C.sub.6-C.sub.30)aromatic ring; [0059] L.sub.2 to L.sub.4 each independently represent a single bond, a substituted or unsubstituted (C.sub.6-C.sub.30)arylene, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; [0060] Ar.sub.5 to Ar.sub.7 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkoxy, a substituted or unsubstituted tri(C.sub.1-C.sub.30)alkylsilyl, a substituted or unsubstituted di(C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted tri(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted fused ring of (C.sub.3-C.sub.30)aliphatic ring and (C.sub.6-C.sub.30)aromatic ring, or *N(R.sub.11)(R.sub.12); may be linked to the adjacent substituents to form a ring(s); provided that at least one of Ar.sub.5 to Ar.sub.7 is a substituted or unsubstituted (C.sub.6-C.sub.30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl; and [0061] R.sub.11 and R.sub.12 each independently represent a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.2-C.sub.30)alkenyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl.
[0062] In one embodiment, at least two of Z.sub.1 to Z.sub.3 may be N.
[0063] In one embodiment, all of Z.sub.1 to Z.sub.3 may be N.
[0064] In one embodiment, R.sub.20 may be hydrogen, deuterium, halogen, cyano, or a substituted or unsubstituted (C.sub.1-C.sub.10)alkyl. For example, R.sub.20 may be hydrogen or deuterium.
[0065] In one embodiment, L.sub.2 to L.sub.4 each independently may be, a single bond, a substituted or unsubstituted (C.sub.6-C.sub.30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene, preferably a single bond, a substituted or unsubstituted (C.sub.6-C.sub.25)arylene or a substituted or unsubstituted (5- to 25-membered)heteroarylene, more preferably a single bond, a substituted or unsubstituted (C.sub.6-C.sub.18)arylene or a substituted or unsubstituted (5- to 18-membered)heteroarylene. For example, L.sub.2 to L.sub.4 each independently may be, a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylphenylene, a substituted or unsubstituted phenylnaphthylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted benzonaphthothiophenylene, or a substituted or unsubstituted benzonaphthofuranylene.
[0066] In one embodiment, Ar.sub.5 to Ar.sub.7 each independently may be, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, or a substituted or unsubstituted tri(C.sub.6-C.sub.30)arylsilyl, preferably a substituted or unsubstituted (C.sub.6-C.sub.25)aryl, a substituted or unsubstituted (5- to 25-membered)heteroaryl, or a substituted or unsubstituted tri(C.sub.6-C.sub.25)arylsilyl, more preferably a substituted or unsubstituted (C.sub.6-C.sub.25)aryl, a substituted or unsubstituted (5- to 18-membered)heteroaryl, or a substituted or unsubstituted tri(C.sub.6-C.sub.18)arylsilyl. Wherein, at least one of Ar.sub.5 to Ar.sub.7 is a substituted or unsubstituted (5- to 30-membered)heteroaryl, preferably at least two of Ar.sub.5 to Ar.sub.7 may be a substituted or unsubstituted (5- to 30-membered)heteroaryl. For example, Ar.sub.5 to Ar.sub.7 each independently may be, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted triphenylsilyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted benzophenanthrenyl, a substituted or unsubstituted chrysenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted benzocarbazolyl, a substituted or unsubstituted benzonaphthofuranyl, a substituted or unsubstituted benzonaphthothiophenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted benzothiazolyl, a substituted or unsubstituted benzoxazolyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted naphthooxazolyl, a substituted or unsubstituted benzonaphthooxazolyl, a substituted or unsubstituted naphthothiazolyl, a substituted or unsubstituted benzonaphthothiazolyl, or a substituted or unsubstituted naphthoimidazolyl. Preferably, Ar.sub.5 to Ar.sub.7 each independently may be, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted triphenylsilyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted chrysenyl, a substituted or unsubstituted triphenyleneyl, a substituted or unsubstituted benzonaphthofuranyl, a substituted or unsubstituted benzonaphthothiophenyl, a substituted or unsubstituted benzonaphthooxazolyl, or a substituted or unsubstituted benzonaphthothiazolyl. Wherein, the substituents of the substituted groups may be at least one selected from the deuterium, cyano, methyl, phenyl, biphenyl, naphthyl, phenanthrenyl, triphenylsilyl, fluorenyl, dibenzothiophenyl, and dibenzofuranyl.
[0067] At least one of Ar.sub.5 to Ar.sub.7 according to one embodiment may be represented by any one of the following Formulas 2-1 to 2-7.
##STR00085## ##STR00086## [0068] In Formulas 2-1 to 2-7, [0069] Y represents O, S, N(R.sub.77), or C(R.sub.78)(R.sub.79); [0070] R.sub.77 represents a site connected to any one of L.sub.2 to L.sub.4, or a substituted or unsubstituted (C.sub.6-C.sub.30)aryl; [0071] R.sub.78 and R.sub.79 each independently represent a site connected to any one of L.sub.2 to L.sub.4, or a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or R.sub.78 and R.sub.79 can be connected to each other to form a ring(s); [0072] R.sub.21 to R.sub.28, R.sub.30 to R.sub.57, and R.sub.59 to R.sub.64 each independently represent a site connected to any one of L.sub.2 to L.sub.4; or hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkoxy, a substituted or unsubstituted tri(C.sub.1-C.sub.30)alkylsilyl, a substituted or unsubstituted di(C.sub.1-C.sub.30)alkyl(C.sub.6C.sub.30)arylsilyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted tri(C.sub.6-C.sub.30)arylsilyl, or a substituted or unsubstituted fused ring of (C.sub.3-C.sub.30)aliphatic ring and (C.sub.6-C.sub.30)aromatic ring; or may be linked to the adjacent substituents to form a ring(s); [0073] X.sub.3 to X.sub.6 each independently represent O, S, Se, or N; and [0074] R.sub.29 and R.sub.58 each independently represent a site connected to any one of L.sub.2 to L.sub.4, or a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl.
[0075] According to one embodiment, the compound represented by Formula 2 may be more specifically illustrated by the following compounds, but is not limited thereto.
##STR00087## ##STR00088## ##STR00089## ##STR00090## ##STR00091## ##STR00092##
##STR00093## ##STR00094## ##STR00095## ##STR00096## ##STR00097## ##STR00098## ##STR00099## ##STR00100## ##STR00101## ##STR00102## ##STR00103## ##STR00104## ##STR00105## ##STR00106## ##STR00107## ##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## ##STR00134## ##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142##
##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161## ##STR00162## ##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171## ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184## ##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190## ##STR00191## ##STR00192##
##STR00193## ##STR00194## ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## ##STR00201## ##STR00202## ##STR00203## ##STR00204## ##STR00205## ##STR00206## ##STR00207## ##STR00208## ##STR00209## ##STR00210## ##STR00211## ##STR00212##
##STR00213## ##STR00214## ##STR00215## ##STR00216## ##STR00217## ##STR00218## ##STR00219## ##STR00220## ##STR00221## ##STR00222## ##STR00223## ##STR00224## ##STR00225## ##STR00226## ##STR00227## ##STR00228## ##STR00229## ##STR00230## ##STR00231## ##STR00232## ##STR00233## ##STR00234## ##STR00235## ##STR00236## ##STR00237## ##STR00238## ##STR00239## ##STR00240## ##STR00241## ##STR00242## ##STR00243## ##STR00244## ##STR00245## ##STR00246## ##STR00247## ##STR00248## ##STR00249## ##STR00250## ##STR00251## ##STR00252## ##STR00253##
##STR00254## ##STR00255## ##STR00256## ##STR00257## ##STR00258## ##STR00259## ##STR00260## ##STR00261## ##STR00262## ##STR00263## ##STR00264## ##STR00265## ##STR00266## ##STR00267## ##STR00268## ##STR00269## ##STR00270## ##STR00271## ##STR00272## ##STR00273## ##STR00274## ##STR00275## ##STR00276## ##STR00277## ##STR00278## ##STR00279## ##STR00280## ##STR00281## ##STR00282## ##STR00283## ##STR00284## ##STR00285## ##STR00286## ##STR00287## ##STR00288## ##STR00289## ##STR00290## ##STR00291## ##STR00292## ##STR00293## ##STR00294## ##STR00295## ##STR00296##
##STR00297## ##STR00298## ##STR00299## ##STR00300## ##STR00301## ##STR00302## ##STR00303## ##STR00304## ##STR00305## ##STR00306## ##STR00307## ##STR00308## ##STR00309## ##STR00310## ##STR00311## ##STR00312## ##STR00313## ##STR00314## ##STR00315## ##STR00316## ##STR00317## ##STR00318## ##STR00319## ##STR00320## ##STR00321## ##STR00322## ##STR00323## ##STR00324## ##STR00325## ##STR00326## ##STR00327## ##STR00328## ##STR00329## ##STR00330## ##STR00331## ##STR00332## ##STR00333## ##STR00334## ##STR00335## ##STR00336## ##STR00337## ##STR00338## ##STR00339## ##STR00340##
##STR00341## ##STR00342## ##STR00343## ##STR00344## ##STR00345## ##STR00346## ##STR00347## ##STR00348## ##STR00349## ##STR00350## ##STR00351## ##STR00352## ##STR00353## ##STR00354## ##STR00355## ##STR00356## ##STR00357## ##STR00358## ##STR00359## ##STR00360## ##STR00361## ##STR00362## ##STR00363## ##STR00364## ##STR00365## ##STR00366## ##STR00367## ##STR00368## ##STR00369## ##STR00370## ##STR00371## ##STR00372## ##STR00373## ##STR00374## ##STR00375## ##STR00376## ##STR00377## ##STR00378## ##STR00379##
##STR00380## ##STR00381## ##STR00382## ##STR00383## ##STR00384## ##STR00385## ##STR00386## ##STR00387## ##STR00388## ##STR00389## ##STR00390## ##STR00391## ##STR00392## ##STR00393## ##STR00394## ##STR00395## ##STR00396## ##STR00397## ##STR00398## ##STR00399## ##STR00400## ##STR00401## ##STR00402## ##STR00403## ##STR00404## ##STR00405## ##STR00406## ##STR00407## ##STR00408## ##STR00409## ##STR00410## ##STR00411## ##STR00412## ##STR00413## ##STR00414## ##STR00415## ##STR00416## ##STR00417## ##STR00418## ##STR00419## ##STR00420## ##STR00421## ##STR00422## ##STR00423## ##STR00424## ##STR00425## ##STR00426## ##STR00427## ##STR00428## ##STR00429## ##STR00430## ##STR00431##
[0076] The compound represented by Formula 2 according to the present disclosure can be manufactured by referring to a synthesis method known to those skilled in the art, for example, the synthesis method disclosed in Korean Patent Application Laid-open No. 10-2020-0092879, etc., but is not limited thereto.
[0077] According to another embodiment of the present disclosure, the present disclosure provides a compound represented by the following Formula 2-1-1.
##STR00432## [0078] In Formula 2-1-1, [0079] L.sub.2 and L.sub.3 each independently represent a single bond, a substituted or unsubstituted (C.sub.6-C.sub.30)arylene, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; [0080] Ar.sub.5 is represented by the following Formula 2-1:
##STR00433## [0081] wherein in Formula 2-1, [0082] Y represents O or S; [0083] R.sub.21 to R.sub.28 each independently represent a site connected to L.sub.2; or hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkoxy, a substituted or unsubstituted tri(C.sub.1-C.sub.30)alkylsilyl, a substituted or unsubstituted di(C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted tri(C.sub.6-C.sub.30)arylsilyl, or a substituted or unsubstituted fused ring of (C.sub.3-C.sub.30)aliphatic ring and (C.sub.6-C.sub.30)aromatic ring; or may be linked to the adjacent substituents to form a ring(s); [0084] Ar.sub.6 represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkoxy, a substituted or unsubstituted tri(C.sub.1-C.sub.30)alkylsilyl, a substituted or unsubstituted di(C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted tri(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted fused ring of (C.sub.3-C.sub.30)aliphatic ring and (C.sub.6-C.sub.30)aromatic ring; or may be linked to the adjacent substituents to form a ring(s); [0085] L.sub.4 represents phenylene unsubstituted or substituted with deuterium or cyano, biphenylene unsubstituted or substituted with deuterium or cyano, or 2-naphthylene unsubstituted or substituted with deuterium or cyano; [0086] Ar.sub.7 represents biphenyl unsubstituted or substituted with deuterium or cyano, naphthyl unsubstituted or substituted with deuterium or cyano, or phenylnaphthyl unsubstituted or substituted with deuterium or cyano;
[0087] Provided that when L.sub.4 is phenylene unsubstituted or substituted with deuterium or cyano, Ar.sub.7 is biphenyl unsubstituted or substituted with deuterium or cyano or naphthyl unsubstituted or substituted with deuterium or cyano; When L.sub.4 is biphenylene unsubstituted or substituted with deuterium or cyano, Ar.sub.7 is naphthyl unsubstituted or substituted with deuterium or cyano; When L.sub.4 is 2-naphthylene unsubstituted or substituted with deuterium or cyano, Ar.sub.7 is biphenyl unsubstituted or substituted with deuterium or cyano, or phenylnaphthyl unsubstituted or substituted with deuterium or cyano.
[0088] In one embodiment, L.sub.4 may be 2-naphthylene selected from the following Group 1, which is unsubstituted or substituted with deuterium or cyano.
##STR00434##
[0089] In Group 1, * represents points connected to Formula 2-1-1 and Ar.sub.7.
[0090] According to one embodiment, the compound represented by Formula 2-1-1 may be more specifically illustrated by the following compounds, but is not limited thereto.
##STR00435## ##STR00436## ##STR00437## ##STR00438## ##STR00439## ##STR00440## ##STR00441## ##STR00442## ##STR00443## ##STR00444## ##STR00445## ##STR00446## ##STR00447##
[0091] According to another embodiment of the present disclosure, the present disclosure provides a compound represented by the following Formula 2-1-2.
##STR00448## [0092] In Formula 2-1-2, [0093] L.sub.2 and L.sub.3 each independently represent a single bond, a substituted or unsubstituted (C.sub.6-C.sub.30)arylene, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; [0094] Ar.sub.5 is represented by the following Formula 2-1:
##STR00449## [0095] wherein in Formula 2-1, [0096] Y represents O or S; [0097] R.sub.21 to R.sub.28 each independently represent a site connected to L.sub.2; or hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkoxy, a substituted or unsubstituted tri(C.sub.1-C.sub.30)alkylsilyl, a substituted or unsubstituted di(C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted tri(C.sub.6-C.sub.30)arylsilyl, or a substituted or unsubstituted fused ring of (C.sub.3-C.sub.30)aliphatic ring and (C.sub.6-C.sub.30)aromatic ring; or may be linked to the adjacent substituents to form a ring(s); [0098] Ar.sub.6 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkoxy, a substituted or unsubstituted tri(C.sub.1-C.sub.30)alkylsilyl, a substituted or unsubstituted di(C.sub.1-C.sub.30)alkyl(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted (C.sub.1-C.sub.30)alkyldi(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted tri(C.sub.6-C.sub.30)arylsilyl, a substituted or unsubstituted fused ring of (C.sub.3-C.sub.30)aliphatic ring and (C.sub.6-C.sub.30)aromatic ring; or may be linked to the adjacent substituents to form a ring(s); and [0099] L.sub.4 represents 1-naphthylene selected from the following Group 2 unsubstituted or substituted with deuterium or cyano:
##STR00450## [0100] wherein in Group 2, * represents points connected to Formula 2-1-2 and Ar.sub.7; and [0101] Ar.sub.7 represents (C.sub.6-C.sub.16)aryl unsubstituted or substituted with deuterium.
[0102] In one embodiment, Ar.sub.7 may be phenyl, p-biphenyl, m-biphenyl, o-biphenyl, or naphthyl, which is unsubstituted or substituted with deuterium.
[0103] According to one embodiment, the compound represented by Formula 2-1-2 may be more specifically illustrated by the following compounds, but is not limited thereto.
##STR00451## ##STR00452## ##STR00453## ##STR00454## ##STR00455## ##STR00456## ##STR00457## ##STR00458## ##STR00459## ##STR00460## ##STR00461## ##STR00462## ##STR00463## ##STR00464## ##STR00465## ##STR00466## ##STR00467## ##STR00468## ##STR00469## ##STR00470## ##STR00471## ##STR00472##
[0104] Hereinafter, an organic electroluminescent device will be described to which the aforementioned compound and/or an organic electroluminescent material comprising the same is (are) applied.
[0105] The organic electroluminescent device according to one embodiment includes a first electrode; a second electrode; and at least one organic layer(s) interposed between the first electrode and the second electrode. The organic layer may include a hole transport layer and a light-emitting layer. According to one embodiment, the hole transport layer may include a compound represented by Formula 1. According to another embodiment, the light-emitting layer may comprise a compound represented by Formula 1 as a first host compound and a compound represented by Formula 2 as a second host compound, respectively. Wherein, the weight ratio of the first host compound to the second host compound may be in the range of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, more preferably about 40:60 to about 60:40, even more preferably about 50:50 in the light-emitting layer.
[0106] According to one embodiment, the organic electroluminescent material of the present disclosure comprises at least one of Compounds H1-1 to H1-262, and at least one of Compounds H2-1 to H2-1261. The organic electroluminescent material may be included in the same organic layer, for example, the same light-emitting layer, or may be included in different light-emitting layers.
[0107] According to another embodiment, the organic electroluminescent device of the present disclosure comprises a first compound represented by Formula 1 and a second compound represented by Formula 2 and may further include a third compound which is selected from the compounds represented by Formulas 1 and 2 and different from the first compound and the second compound. For example, the organic electroluminescent device of the present disclosure includes one of Compounds H1-1 to H1-262, which is a first compound, one of Compounds H2-1 to H2-1261, which is a second compound, as a host material of the light-emitting layer, and may further include one of Compounds H1-1 to H1-262 and H2-1 to H2-1261, which is a third compound different from the first compound and the second compound.
[0108] According to another embodiment, the present disclosure may provide an organic electroluminescent device comprising a compound represented by Formula 2-1-1. According to the other embodiment, the present disclosure may provide an organic electroluminescent device comprising a compound represented by Formula 2-1-2.
[0109] The organic layer may further comprise at least one layer selected from a hole injection layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, an interlayer, a hole-blocking layer, an electron-blocking layer and an electron buffer layer, in addition to the hole transport layer and the light-emitting layer. The organic layer may further comprise an amine-based compound and/or an azine-based compound other than the light-emitting material according to the present disclosure. Specifically, the hole injection layer, the hole transport layer, the hole auxiliary layer, the light-emitting layer, the light-emitting auxiliary layer, or the electron-blocking layer may contain the amine-based compound, e.g., an arylamine-based compound and a styrylarylamine-based compound, etc., as a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting material, a light-emitting auxiliary material, or an electron-blocking material. Further, the electron transport layer, the electron injection layer, the electron buffer layer, or the hole-blocking layer may contain the azine-based compound as an electron transport material, an electron injection material, an electron buffer material, or a hole-blocking material. Further, the organic layer may further comprise at least one metal selected from the group consisting of metals from Group 1, metals from Group 2, transition metals of the 4.sup.th period, transition metals of the 5.sup.th period, lanthanides, and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising such a metal.
[0110] The organic electroluminescent material according to one embodiment may be used as light-emitting materials for a white organic light-emitting device. The white organic light-emitting device has suggested various structures such as a parallel side-by-side arrangement method, a stacking arrangement method, CCM (color conversion material) method, etc., according to the arrangement of R (red), G (green), YG (yellowish green), or B (blue) light-emitting units. In addition, the compound or the organic electroluminescent material according to one embodiment may also be applied to the organic electroluminescent device comprising a QD (quantum dot).
[0111] One of the first electrode and the second electrode may be an anode and the other may be a cathode. Wherein, the first electrode and the second electrode may each be formed as a transmissive conductive material, a transflective conductive material, or a reflective conductive material. The organic electroluminescent device may be a top emission type, a bottom emission type, or a dual-side emission type according to the kinds of the material forming the first electrode and the second electrode.
[0112] A hole injection layer, a hole transport layer, an electron-blocking layer, or a combination thereof can be used between the anode and the light-emitting layer. The hole injection layer may be multi-layered in order to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron-blocking layer, wherein each of the multi-layers may use two compounds simultaneously. Also, the hole injection layer may be doped as a p-dopant. Also, the electron-blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can confine the excitons within the light-emitting layer by blocking the overflow of electrons from the light-emitting layer to prevent a light-emitting leakage. The hole transport layer or the electron-blocking layer may be multi-layered, and wherein each layer may use a plurality of compounds.
[0113] An electron buffer layer, a hole-blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode. The electron buffer layer may be multi-layered in order to control the injection of the electron and improve the interfacial properties between the light-emitting layer and the electron injection layer, wherein each of the multi-layers may use two compounds simultaneously. The hole-blocking layer may be placed between the electron transport layer (or electron injection layer) and the light-emitting layer, and blocks the arrival of holes to the cathode, thereby improving the probability of recombination of electrons and holes in the light-emitting layer. The hole-blocking layer or the electron transport layer may also be multi-layered, wherein each layer may use a plurality of compounds. Further, the electron injection layer may be doped as an n-dopant.
[0114] The light-emitting auxiliary layer may be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it can be used for promoting the hole injection and/or the hole transport, or for preventing the overflow of electrons. When the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it can be used for promoting the electron injection and/or the electron transport, or for preventing the overflow of holes. In addition, the hole auxiliary layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may be effective to promote or block the hole transport rate (or the hole injection rate), thereby enabling the charge balance to be controlled. When an organic electroluminescent device includes two or more hole transport layers, the hole transport layer, which is further included, may be used as the hole auxiliary layer or the electron-blocking layer. The light-emitting auxiliary layer, the hole auxiliary layer, or the electron-blocking layer may have an effect of improving the efficiency and/or the lifespan of the organic electroluminescent device.
[0115] In the organic electroluminescent device of the present disclosure, preferably, at least one layer (hereinafter, a surface layer) selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer may be placed on an inner surface(s) of one or both of a pair of electrodes. Specifically, a chalcogenide (including oxides) layer of silicon and aluminum is preferably placed on an anode surface of an electroluminescent medium layer, and a halogenated metal layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer. The operation stability for the organic electroluminescent device may be obtained by the surface layer. Preferably, the chalcogenide includes SiO.sub.x(1x2), AlO.sub.x(1x1.5), SiON, SiAlON, etc.; the halogenated metal includes LiF, MgF.sub.2, CaF.sub.2, a rare earth metal fluoride, etc.; and the metal oxide includes Cs.sub.2O, Li.sub.2O, MgO, SrO, BaO, CaO, etc.
[0116] In addition, in the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium. Furthermore, the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds, and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. Further, a reductive dopant layer may be employed as a charge generating layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.
[0117] The organic electroluminescent device according to one embodiment of the present disclosure may be an organic electroluminescent device having a tandem structure. In the case of a tandem organic electroluminescent device according to one embodiment, a single light-emitting unit (light-emitting unit) may be formed in a structure in which two or more units are connected by a charge generation layer. The organic electroluminescent device may include a plurality of two or more light emitting units, for example, a plurality of three or more light-emitting units, having first and second electrodes opposed to each other on a substrate and a light emitting layer that is stacked between the first and second electrodes and emits light in a specific wavelength range. According to one embodiment, the organic electroluminescent device may include a plurality of light-emitting units, and each of the light-emitting units may include a hole transport band, a light-emitting layer, and an electron transport band, and the hole transport band may include a hole injection layer and a hole transport layer, and the electron transfer zone may include an electron transport layer and an electron injection layer. According to one embodiment, three or more light emitting layers may be included in the light emitting unit. A plurality of light emitting units may emit the same color or different colors. Additionally, one light emitting unit may include one or more light emitting layers, and the plurality of light emitting layers may be light emitting layers of the same or different colors. It may include one or more charge generation layers located between each light-emitting unit. The charge generation layer refers to the layer in which holes and electrons are generated when voltage is applied. When there are three or more light-emitting units, a charge generation layer may be located between each light-emitting unit. At this time, the plurality of charge generation layers may be the same or different from each other. By disposing the charge generation layer between light-emitting units, current efficiency is increased in each light-emitting unit and charges can be smoothly distributed. Specifically, the charge generation layer is provided between two adjacent stacks and can serve to drive a tandem organic electroluminescent device using only a pair of anodes and cathodes without a separate internal electrode located between the stacks.
[0118] The charge generation layer may be composed of an n-type charge generation layer and a p-type charge generation layer, and the n-type charge generation layer may be doped with an alkali metal, an alkaline earth metal, or a compound of an alkali metal and an alkaline earth metal. The alkali metal may include one selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb, and combinations thereof, and the alkaline earth metal may include one selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra, and combinations thereof. The p-type charge generation layer may be made of a metal or an organic material doped with a p-type dopant. For example, the metal may be made of one or two or more alloys selected from the group consisting of Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti. Additionally, commonly used materials may be used as the p-type dopant and host materials used in the p-type doped organic material.
[0119] An organic electroluminescent device according to one embodiment may further comprise at least one dopant in the light-emitting layer.
[0120] The dopant comprised in the organic electroluminescent device of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but may be preferably a metallated complex compound(s) of a metal atom(s) selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably an ortho-metallated complex compound(s) of a metal atom(s) selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compound(s).
[0121] The dopant comprised in the organic electroluminescent device of the present disclosure may use the compound represented by the following Formula 101, but is not limited thereto.
##STR00473## [0122] In Formula 101, [0123] L is selected from any one of the following Structures 1 to 3;
##STR00474## [0124] R.sub.100 to R.sub.103 each independently represent hydrogen, deuterium, halogen, (C.sub.1-C.sub.30)alkyl unsubstituted or substituted with deuterium and/or halogen, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, cyano, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C.sub.1-C.sub.30)alkoxy; or may be linked to the adjacent substituents to form a ring(s), for example, to form a ring(s) with a pyridine, e.g., a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuropyridine, a substituted or unsubstituted benzothienopyridine, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuroquinoline, a substituted or unsubstituted benzothienoquinoline, or a substituted or unsubstituted indenoquinoline; [0125] R.sub.104 to R.sub.107 each independently represent hydrogen, deuterium, halogen, (C.sub.1-C.sub.30)alkyl unsubstituted or substituted with deuterium and/or halogen, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, a substituted or unsubstituted (C.sub.6-C.sub.30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, cyano, or a substituted or unsubstituted (C.sub.1-C.sub.30)alkoxy; or may be linked to the adjacent substituents to form a substituted or unsubstituted ring(s), for example, to form a substituted or unsubstituted ring(s) with a benzene, e.g., a substituted or unsubstituted naphthalene, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuropyridine, or a substituted or unsubstituted benzothienopyridine; [0126] R.sub.201 to R.sub.220 each independently represent hydrogen, deuterium, halogen, (C.sub.1-C.sub.30)alkyl unsubstituted or substituted with deuterium and/or halogen, a substituted or unsubstituted (C.sub.3-C.sub.30)cycloalkyl, or a substituted or unsubstituted (C.sub.6-C.sub.30)aryl; or may be linked to the adjacent substituents to form a substituted or unsubstituted ring(s); and [0127] s represents an integer of 1 to 3.
[0128] Specifically, the specific examples of the dopant compound include the following, but are not limited thereto.
##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##
[0129] In order to form each layer of the organic electroluminescent device of the present disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc. or wet film-forming methods such as spin coating, dip coating, flow coating methods, etc. can be used. When using a wet film-forming method, a thin film may be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent may be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
[0130] When depositing an organic electroluminescent material according to one embodiment, the layer can be formed by the above-listed methods, and can often be formed by co-deposition or mixture-deposition. The co-deposition is a mixed deposition method in which two or more materials are put into respective individual crucible sources and a current is applied to both cells simultaneously to evaporate the materials; and the mixed deposition is a method in which two or more materials are mixed in one crucible source before the deposition, and then a current is applied to one cell to evaporate the materials.
[0131] According to one embodiment, the present disclosure can provide display devices comprising a compound represented by Formula 1 and/or display devices comprising an organic electroluminescent material including a first host compound represented by Formula 1 and a second host compound represented by Formula 2. In addition, by using the organic electroluminescent device of the present disclosure, display devices such as smartphones, tablets, notebooks, PCs, TVs, or display devices for vehicles, or lighting devices such as outdoor or indoor lighting can be prepared.
[0132] Hereinafter, the preparation method of the compound according to the present disclosure will be explained with reference to the synthesis method of a representative compound or intermediate compound in order to understand the present disclosure in detail.
[Example 1] Synthesis of Compound H1-2
##STR00513##
[0133] Compound P-1 (4 g, 9.8 mmol), N-phenyldibenzo[b,d]furan-3-amine (2.8 g, 10.7 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd.sub.2(dba).sub.3) (459 mg, 0.5 mmol), dicyclohexyl[2,6-dimethoxy[1,1-biphenyl]-2-yl]phosphine (S-Phos) (443 mg, 1.07 mmol), sodium tert-butoxide (NaOtBu) (1.56 g, 16.2 mmol), and 72 mL of xylene were added to a flask and dissolved, and then stirred under reflux for 1 hour. After the reaction was completed, the organic layer was extracted with ethyl acetate the residual moisture removed with magnesium sulfate, and this was then separated by way of column chromatography to obtain Compound H1-2 (3.3 g, 54%).
TABLE-US-00001 MW M.P. H1-2 628.22 239.1 C.
[Example 2] Synthesis of Compound H1-1
##STR00514##
[0134] Compound P-1 (5 g, 12.3 mmol), N-phenyldibenzo[b,d]furan-2-amine (2.9 g, 11.2 mmol), Pd.sub.2(dba).sub.3 (512 mg, 0.56 mmol), S-Phos (459 mg, 1.12 mmol), NaOtBu (1.61 g, 16.8 mmol), and 56 mL of xylene were added to a flask and dissolved, and then stirred under reflux at 1 hour. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual moisture removed with magnesium sulfate, and this was then separated by way of column chromatography to obtain Compound H1-1 (3.2 g, 45.5%).
TABLE-US-00002 MW M.P. H1-1 628.22 237.8 C.
[Example 3] Synthesis of Compound H1-206
##STR00515##
[0135] Compound P-2 (5 g, 10.96 mmol), N-phenyldibenzo[b,d]furan-2-amine (4.7 g, 13.16 mmol), Pd.sub.2(dba).sub.3 (0.5 g, 0.548 mmol), NaOtBu (1.6 g, 16.45 mmol), S-Phos (0.45 g, 1.096 mmol), and 60 mL of xylene were added to a flask and dissolved, and then stirred under reflux at 1 hour. After the reaction was completed, the mixture was cooled to room temperature, filtered through a Celite filter, and then distilled under reduced pressure. The separation was then performed by way of column chromatography to obtain Compound H1-206 (1.8 g, 24%).
TABLE-US-00003 MW M.P. H1-206 678.7 214.6 C.
[Example 4] Synthesis of Compound H1-49
##STR00516##
[0136] 120 mL of xylene was added to Compound P-1 (10 g, 24.63 mmol), Compound 2 (9.9 g, 29.56 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.1 g, 1.231 mmol), sodium tert-butoxide (3.5 g, 36.95 mmol), and S-Phos (1 g, 2.463 mmol), and then stirred under reflux at 160 C. for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, filtered through a Celite filter, and then distilled under reduced pressure. The separation was then performed by way of column chromatography to obtain Compound H1-49 (3.5 g, 40%).
TABLE-US-00004 MW M.P. H1-49 704.8 270.1 C.
[Example 5] Synthesis of Compound H1-60
##STR00517##
[0137] 50 mL of xylene was added to Compound P-2 (4 g, 8.773 mmol), Compound 3 (2.6 g, 10.52 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.4 g, 0.438 mmol), sodium tert-butoxide (1.3 g, 13.16 mmol), and S-Phos (0.36 g, 0.877 mmol) and then stirred under reflux at 160 C. for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, filtered through a Celite filter, and then distilled under reduced pressure. The separation was then performed by way of column chromatography to obtain Compound H1-60 (2.9 g, 50%).
TABLE-US-00005 MW M.P. H1-60 664.7 286 C.
[Example 6] Synthesis of Compound H1-212
##STR00518##
[0138] Compound P-1 (14 g, 34.737 mmol), Compound 4 (12 g, 34.737 mmol), NaOtBu (8.4 g, 86.84 mmol), S-Phos (1.4 g, 3.473 mmol), Pd.sub.2(dba).sub.3 (1.6 g, 3.473 mmol), and 173 mL of xylene were added to a flask and dissolved, and the stirred under reflux at 160 C. for 12 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual moisture removed with magnesium sulfate, and this was then separated by way of column chromatography to obtain Compound H1-212 18.0 g (Yield: 75%).
TABLE-US-00006 MW M.P. H1-212 714.87 265 C.
[0139] Hereinafter, the preparation method of an organic electroluminescent device comprising the compound according to the present disclosure and an organic electroluminescent material comprising the compound, and the device property thereof will be explained in order to understand the present disclosure in detail.
[Device Examples 1 and 2] Preparation of OLEDs Comprising the Compound According to the Present Disclosure as a Hole Transport Layer Material
[0140] OLEDs according to the present disclosure were produced. First, a transparent electrode indium tin oxide (ITO) thin film (10 /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 thereafter was stored in isopropyl alcohol and then used. Thereafter, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Then, Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and Compound HT-1 was introduced into another cell. The two materials were evaporated at different rates, and Compound HI-1 was deposited in a doping amount of 3 wt % based on the total amount of Compounds HI-1 and HT-1 to form a hole injection layer having a thickness of 10 nm. Next, Compound HT-1 was deposited as a first hole transport layer having a thickness of 80 nm on the hole injection layer. The compound described in the following Table 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 second hole transport layer having a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layers, a light-emitting layer was formed thereon as follows: each of the first host Compound A and the second host Compound H2-1 were introduced into two cells of the vacuum vapor deposition apparatus as hosts, respectively, and Compound D-39 was introduced into another cell as a dopant. The two host materials were evaporated at a rate of 1:1, and the dopant material was evaporated at a different rate, simultaneously, and was deposited in a doping amount of 3 wt % based on the total amount of the hosts and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer. Next, Compounds ET-1 and EI-1, as electron transport materials, were deposited at a weight ratio of 50:50 to form an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing Compound EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, OLEDs were produced. Each compound used for all of the materials was purified by vacuum sublimation at 10.sup.6 Torr.
[Device Comparative Example 1] Preparation of an OLED Containing the Conventional Compound as a Hole Transport Layer Material
[0141] An OLED was manufactured in the same manner as in Device Example 1, except that the compound described in the following Table 1 as the second hole transport layer material was used.
[0142] The driving voltage, the luminous efficiency, and the luminous color at a luminance of 1,000 nits and the time taken for luminance to decrease from 100% to 95% at a luminance of 10,000 nits (lifespan: T.sub.95) of the OLED devices of Device Examples 1 and 2 and Device Comparative Example 1 produced as described above were measured, and the results thereof are shown in the following Table 1.
TABLE-US-00007 TABLE 1 Second Hole Driving Luminous Transport Voltage Efficiency Luminous Lifespan Layer (V) (cd/A) Color (T.sub.95, hr) Device H1-1 2.8 26.3 Red 39 Example 1 Device H1-2 2.7 30.4 Red 130 Example 2 Device F 4.1 21.0 Red 32 Comparative Example 1
[0143] As shown in Table 1, it can be seen that the organic electroluminescent device in which the compound according to the present disclosure is deposited as the hole transport layer material has low driving voltage and/or high luminous efficiency and/or significantly improved long-lifespan characteristics compared to the organic electroluminescent device including the conventional compound as the hole transport layer material.
[0144] HOMO (Highest Occupied Molecular Orbital) level and glass transition temperature (T.sub.g) of each of Compounds H1-1, H1-2, and F used in Device Examples 1 and 2 and Device Comparative Example 1 were measured and are shown in Table 2 below.
TABLE-US-00008 TABLE 2 HOMO T.sub.g
[0145] From the results in Table 2 above, compared to Compound F used in Device Comparative Example 1, Compounds H1-1 and H1-2 used in Device Examples 1 and 2 according to the present disclosure have a low HOMO energy level and act on holes quickly to help smooth hole injection, providing an advantage in terms of driving voltage. In addition, it can be seen that along with better luminous characteristics due to high hole mobility, there is also a significant increase in lifespan characteristics based on the high glass transition temperature.
[Device Examples 3 to 36] Preparation of OLEDs Comprising the Organic Electroluminescent Material According to the Present Disclosure
[0146] OLEDs were manufactured in the same manner as in Device Example 1, except that Compound HT-2 was used as the second hole transport layer material, the compound shown in Table 3 below was used as the host material of the light-emitting layer, and Compound ET-2 was used as the electron transport layer material.
[Device Comparative Examples 2 and 3] Preparation of OLEDs Comprising the Conventional Compound as a Host Material
[0147] OLEDs were manufactured in the same manner as in Device Example 3, except that the compound shown in Table 3 below was used alone as the host material of the light-emitting layer.
[0148] The driving voltage, the luminous efficiency, and the luminous color at a luminance of 1,000 nits and the time taken for luminance to decrease from 100% to 95% at a luminance of 10,000 nits (lifespan: T.sub.95) of the OLED devices of Device Examples 3 to 36 and Device Comparative Examples 2 and 3 produced as described above were measured, and the results thereof are shown in the following Table 3.
TABLE-US-00009 TABLE 3 Driving Luminous Second Voltage Efficiency Luminous Lifespan First Host Host (V) (cd/A) Color (T95, hr) Device H2-77 3.5 31.8 Red 18 Comparative Example 2 Device H2-1 3.0 25.3 Red 17 Comparative Example 3 Device H1-1 H2-77 2.9 33.5 Red 350 Example 3 Device H1-2 H2-77 3.0 34.6 Red 411 Example 4 Device H1-1 H2-1 2.8 30.7 Red 238 Example 5 Device H1-2 H2-1 2.9 32.4 Red 289 Example 6 Device H1-2 H2-77 2.9 31.8 Red 292 Example 7 Device H1-2 H2-1 2.9 27.9 Red 176 Example 8 Device H1-2 H2-1085 2.8 33.7 Red 387 Example 9 Device H1-2 H2-817 2.8 33.0 Red 271 Example 10 Device H1-2 H2-826 2.9 33.4 Red 383 Example 11 Device H1-2 H2-845 2.9 33.2 Red 271 Example 12 Device H1-2 H2-1008 2.8 32.5 Red 279 Example 13 Device H1-2 H2-99 3.1 33.3 Red 246 Example 14 Device H1-2 H2-790 2.9 32.8 Red 323 Example 15 Device H1-2 H2-778 2.8 32.6 Red 367 Example 16 Device H1-2 H2-1050 2.8 32.5 Red 248 Example 17 Device H1-2 H2-1049 2.8 33.8 Red 340 Example 18 Device H1-2 H2-1022 2.8 33.1 Red 365 Example 19 Device H1-2 H2-771 2.8 33.1 Red 276 Example 20 Device H1-2 H2-953 2.9 34.5 Red 293 Example 21 Device H1-2 H2-1027 2.8 33.4 Red 308 Example 22 Device H1-132 H2-1085 2.82 34.5 Red 381 Example 23 Device H1-132 H2-817 2.85 33.4 Red 266 Example 24 Device H1-132 H2-826 2.85 33.9 Red 416 Example 25 Device H1-132 H2-845 2.29 34.0 Red 294 Example 26 Device H1-132 H2-1008 2.83 33.4 Red 308 Example 27 Device H1-132 H2-99 3.02 33.7 Red 282 Example 28 Device H1-132 H2-790 2.86 33.2 Red 287 Example 29 Device H1-132 H2-778 2.83 33.1 Red 368 Example 30 Device H1-132 H2-1050 2.81 33.3 Red 242 Example 31 Device H1-132 H2-1049 2.84 34.2 Red 317 Example 32 Device H1-132 H2-1022 2.82 33.9 Red 392 Example 33 Device H1-132 H2-771 2.82 33.8 Red 298 Example 34 Device H1-132 H2-953 2.88 34.9 Red 278 Example 35 Device H1-132 H2-1027 2.83 33.7 Red 308 Example 36
[0149] As shown in Table 3 above, it can be seen that the organic electroluminescent device containing the organic electroluminescent material according to the present disclosure as a host material exhibits lower driving voltage and/or higher luminous efficiency and/or superior lifespan characteristics compared to organic electroluminescent devices containing the conventional host material.
[0150] The compounds used in the Device Examples and the Device Comparative Example above are shown in the following Table 4.
TABLE-US-00010 TABLE 4 Hole Injection Layer/Hole Transport Layer