COMPOUND FOR ORGANIC ELECTRIC ELEMENT, ORGANIC ELECTRIC ELEMENT USING SAME, AND ELECTRONIC DEVICE HAVING SAME
20230183201 · 2023-06-15
Assignee
Inventors
- Se Hoon LEE (Cheonan-si, Chungcheongnam-do, KR)
- Hyung Dong LEE (Cheonan-si, Chungcheongnam-do, KR)
- Dae Hwan OH (Cheonan-si, Chungcheongnam-do, KR)
- Won Sam KIM (Cheonan-si, Chungcheongnam-do, KR)
- Sun Hee LEE (Cheonan-si, Chungcheongnam-do, KR)
- Soung Yun MUN (Cheonan-si, Chungcheongnam-do, KR)
- Jeong Seok KIM (Cheonan-si, Chungcheongnam-do, KR)
Cpc classification
C07D409/12
CHEMISTRY; METALLURGY
C07D405/12
CHEMISTRY; METALLURGY
H10K85/631
ELECTRICITY
C07D311/78
CHEMISTRY; METALLURGY
H10K85/6574
ELECTRICITY
H10K85/626
ELECTRICITY
C07D405/04
CHEMISTRY; METALLURGY
H10K85/6572
ELECTRICITY
C07D335/10
CHEMISTRY; METALLURGY
C07B2200/05
CHEMISTRY; METALLURGY
H10K85/633
ELECTRICITY
H10K85/636
ELECTRICITY
H10K85/615
ELECTRICITY
H10K85/6576
ELECTRICITY
Y02E10/549
GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
C07D407/12
CHEMISTRY; METALLURGY
International classification
C07D311/78
CHEMISTRY; METALLURGY
C07D335/10
CHEMISTRY; METALLURGY
C07D405/12
CHEMISTRY; METALLURGY
C07D407/12
CHEMISTRY; METALLURGY
C07D409/12
CHEMISTRY; METALLURGY
Abstract
Provided are a compound capable of improving the luminous efficiency, stability and lifespan of a device employing the same, an organic electronic element using the same, and an electronic device thereof.
Claims
1. A compound represented by Formula 1: ##STR00509## wherein: 1) X is O or S, 2) a and b are each independently 0 or 1, provided that a+b is 1 or more, 3) Ar.sup.1 and Ar.sup.2 are each independently selected from the group consisting of a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; and a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring, 4) L.sup.1 L.sup.2, L.sup.3, L.sup.4, L.sup.5 and L.sup.6 are each independently selected from the group consisting of a single bond; an C.sub.6-C.sub.60 arylene group; a fluorenylene group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; and a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring, 5) i) where a is 0, R.sup.1 is independently selected from the group consisting of hydrogen; deuterium; tritium; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxyl group; a C.sub.6-C.sub.60 aryloxy group; a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heteroaryl group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; or R.sup.1 and R.sup.2 are bonded to each other to form a ring, ii) where a is 1, R.sup.1 is Z; wherein Z is selected from the group consisting of a C.sub.6-C.sub.60 arylene group; a fluorenylene group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; or Z and R.sup.2 may be bonded to each other to form a ring, 6) R.sup.2 is independently selected from the group consisting of hydrogen; deuterium; tritium; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxyl group; a C.sub.6-C.sub.60 aryloxy group; a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring, 7) R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are independently selected from the group consisting of hydrogen; deuterium; tritium; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxyl group; a C.sub.6-C.sub.60 aryloxy group; a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring, wherein in case m, n, o, p, q, r, s and t are 2 or more, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.10, R.sup.11 and R.sup.12 are each in plural being the same or different, and or a plurality of R.sup.3 or a plurality of R.sup.4 or a plurality of R.sup.5 or a plurality of R.sup.6 or a plurality of R.sup.7 or a plurality of R.sup.10 or a plurality of R.sup.11 or a plurality of R.sup.12 may be bonded to each other to form a ring, 8) R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are may be bonded to each other to form a ring, with the proviso that R.sup.5 and R.sup.8, or R.sup.9 and R.sup.12, are not bonded to each other to form a ring, 9) m, n, o, p, q, r, s and t are each independently an integer from 0 to 4, 10) wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C.sub.1-C.sub.20 alkylthio group; C.sub.1-C.sub.20 alkoxyl group; C.sub.1-C.sub.20 alkyl group; C.sub.2-C.sub.20 alkenyl group; C.sub.2-C.sub.20 alkynyl group; C.sub.6-C.sub.20 aryl group; C.sub.6-C.sub.20 aryl group substituted with deuterium; a fluorenyl group; C.sub.2-C.sub.20 heterocyclic group; C.sub.3-C.sub.20 cycloalkyl group; C.sub.7-C.sub.20 arylalkyl group; and C.sub.8-C.sub.20 arylalkenyl group; also the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term ‘ring’ means a C.sub.3-C.sub.60 aliphatic ring or a C.sub.6-C.sub.60 aromatic ring or a C.sub.2-C.sub.60 heterocyclic group or a fused ring formed by the combination thereof.
2. The compound of claim 1, wherein the compound represented by Formula 1 is represented by Formula 2 or Formula 3: ##STR00510## ##STR00511## wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 R.sup.7 R.sup.8 R.sup.9 R.sup.10,R.sup.11,R.sup.12, L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, L.sup.6, Ar.sup.1, Ar.sup.2, Z, m, n, o, p, q, r, s and t are the same as defined in claim 1.
3. The compound of claim 1, wherein the compound represented by Formula 1 is represented by any one of Formulas 4 to 9: ##STR00512## ##STR00513## ##STR00514## ##STR00515## ##STR00516## ##STR00517## R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10,R.sup.11, R.sup.12, L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, L.sup.6, Ar.sup.1, Ar.sup.2, Z, m, n, o, p, q, r, s and t are the same as defined in claim 1.
4. The compound of claim 1, wherein the compound represented by Formula 1 is represented by any one of Formulas 10 to 13: ##STR00518## ##STR00519## ##STR00520## ##STR00521## wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, L.sup.1, L.sup.2, L.sup.3, Ar.sup.1, m, n, o, p, and q are the same as defined in claim 1.
5. The compound of claim 1, wherein Ar.sup.1 or Ar.sup.2 is represented by Formula 1-1: ##STR00522## wherein: 1) Y is O, S, NR.sup.b or CR’R″, 2) R.sup.13, R.sup.14, R.sup.b, R′ and R″ are independently selected from the group consisting of hydrogen; deuterium; tritium; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C60 alkoxyl group; a C.sub.6-C.sub.60 aryloxy group; a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring, or a plurality of adjacent R.sup.13, or a plurality of R.sup.14, or R′ and R″ may be bonded to each other to form a ring, 3) w is an integer of 0 to 3, x is an integer of 0 to 4, 4) indicates the position to be bonded.
6. The compound of claim 1, wherein the compound represented by Formula 1 is represented by Formula 14 or Formula 15: ##STR00523## ##STR00524## wherein: 1) X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, L.sup.6, Z, m, n, o, p, q, r, s, and t are the same as defined in claim 1, 2) Y is O, S, NR.sup.b or CR’R″, 3) R.sup.13 and R.sup.14 are independently selected from the group consisting of hydrogen: deuterium; tritium; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxyl group; a C.sub.6-C.sub.60 aryloxy group; a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring, or a plurality of adjacent R.sup.13, or a plurality of R.sup.14, or R′ and R″ may be bonded to each other to form a ring, 4) w is an integer of 0 to 3, and x is an integer of 0 to 4.
7. The compound of claim 1, wherein the compound represented by Formula 1 is represented by any one of Formulas 16 to 21: ##STR00525## ##STR00526## ##STR00527## ##STR00528## ##STR00529## ##STR00530## wherein: 1) X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10,R.sup.11,R.sup.12, L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, L.sup.6, Z, m, n, o, p, q, r, s and t are the same as defined in claim 1, 2) Y is O, S, NR.sup.b or CR’R″, 3) R.sup.13 and R.sup.14 are independently selected from the group consisting of hydrogen: deuterium; tritium; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxyl group; a C.sub.6-C.sub.60 aryloxy group; a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring, or a plurality of adjacent R.sup.13, or a plurality of R.sup.14, or R′ and R″ may be bonded to each other to form a ring, 4) w is an integer of 0 to 3, and x is an integer of 0 to 4.
8. The compound of claim 1, wherein the compound represented by Formula 1 is represented by any one of Formulas 22 to 25: ##STR00531## ##STR00532## ##STR00533## ##STR00534## wherein: 1) X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, L.sup.1, L.sup.2, L.sup.3, m, n, o, p and q are the same as defined in claim 1, 2) Y is O, S, NR.sup.b or CR’R″, 3) R.sup.13 and R.sup.14 are independently selected from the group consisting of hydrogen: deuterium; tritium; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxyl group; a C.sub.6-C.sub.60 aryloxy group; a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring, or a plurality of adjacent R.sup.13, or a plurality of R.sup.14, or R′ and R″ may be bonded to each other to form a ring, 4) w is an integer of 0 to 3, and x is an integer of 0 to 4.
9. The compound of claim 5, wherein the compound represented by Formula 1-1 is represented by any one of Formulas 1-2 to 1-5: ##STR00535## ##STR00536## ##STR00537## ##STR00538## wherein: Y, R.sup.13, R.sup.14, w and x are the same as defined in claim 5, ##STR00539## indicates the position to be bonded.
10. The compound of claim 1, wherein the compound represented by Formula 1 is any one of the following compounds P1-1 to P7-4: ##STR00540## ##STR00541## ##STR00542## ##STR00543## ##STR00544## ##STR00545## ##STR00546## ##STR00547## ##STR00548## ##STR00549## ##STR00550## ##STR00551## ##STR00552## ##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## ##STR00626## ##STR00627## ##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## .
11. An organic electronic element comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer comprises a single compound or 2 or more compounds represented by Formula 1 of claim 1.
12. The organic electronic element of claim 11, wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, an emitting-auxiliary layer, an emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.
13. The organic electronic element of claim 11, wherein the organic material layer comprises a hole transport layer comprising the compound.
14. The organic electronic element of claim 11, wherein the organic material layer comprises an emitting auxiliary layer comprising the compound.
15. The organic electronic element of claim 11, wherein the organic material layer comprises an emitting layer comprising the compound as a phosphorescent host material .
16. The organic electronic element of claim 11, wherein the organic electronic element further comprises a light efficiency enhancing layer formed on at least one surface of the anode and the cathode, the surface being opposite to the organic material layer.
17. The organic electronic element of claim 11, wherein the organic material layer comprises 2 or more stacks, each stack comprising a hole transport layer, an emitting layer, and an electron transport layer sequentially formed on the anode.
18. The organic electronic element of claim 17, wherein the organic material layer further comprises a charge generation layer formed between the 2 or more stacks.
19. An electronic device comprising: a display device including the organic electronic element of claim 11; and a control unit for driving the display device.
20. The organic electronic device of claim 19, wherein the organic electronic element is any one of an organic electroluminescent device (OLED), an organic solar cell, an organic photo conductor (OPC), an organic transistor (organic TFT), and an element for monochromic or white illumination.
Description
BRIEF DESCRIPTION OF THE DRAWINGS
[0018]
[0019]
[0020] 100, 200, 300: organic electronic element [0021] 110 : the first electrode [0022] 120 : hole injection layer [0023] 130 : hole transport layer [0024] 140 : emitting layer [0025] 150 : electron transport layer [0026] 170 : second electrode [0027] 180 : light efficiency enhancing Layer [0028] 210 : buffer layer [0029] 220 : emitting-auxiliary layer [0030] 330 : first hole transport layer [0031] 340 : first emitting layer [0032] 350 : first electron transport layer [0033] 360 : first charge generation layer [0034] 361 : second charge generation layer [0035] 420 : second hole injection layer [0036] 430 : second hole transport layer [0037] 440 : second emitting layer [0038] 450 : second electron transport layer [0039] CGL: charge generation layer [0040] ST1 : first stack [0041] ST2 : second stack
DETAILED DESCRIPTION
[0042] Hereinafter, some embodiments of the present invention will be described in detail.
[0043] Further, in the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.
[0044] In addition, terms, such as first, second, A, B, (a), (b) or the like may be used herein when describing components of the present invention. Each of these terminologies is not used to define an essence, order or sequence of a corresponding component but used merely to distinguish the corresponding component from other component(s). It should be noted that if a component is described as being “connected”, “coupled”, or “connected” to another component, the component may be directly connected or connected to the other component, but another component may be “connected”, “coupled” or “connected” between each component.
[0045] As used in the specification and the accompanying claims, unless otherwise stated, the following is the meaning of the term as follows.
[0046] Unless otherwise stated, the term “halo” or “halogen”, as used herein, includes fluorine, bromine, chlorine, or iodine.
[0047] Unless otherwise stated, the term “alkyl” or “alkyl group”, as used herein, has a single bond of 1 to 60 carbon atoms, and means saturated aliphatic functional radicals including a linear alkyl group, a branched chain alkyl group, a cycloalkyl group (alicyclic), an cycloalkyl group substituted with a alkyl or an alkyl group substituted with a cycloalkyl.
[0048] Unless otherwise stated, the term “alkenyl” or “alkynyl”, as used herein, has double or triple bonds of 2 to 60 carbon atoms, but is not limited thereto, and includes a linear or a branched chain group.
[0049] Unless otherwise stated, the term “cycloalkyl”, as used herein, means alkyl forming a ring having 3 to 60 carbon atoms, but is not limited thereto.
[0050] Unless otherwise stated, the term “alkoxyl group”, “alkoxy group” or “alkyloxy group”, as used herein, means an oxygen radical attached to an alkyl group, but is not limited thereto, and has 1 to 60 carbon atoms.
[0051] Unless otherwise stated, the term “aryloxyl group” or “aryloxy group”, as used herein, means an oxygen radical attached to an aryl group, but is not limited thereto, and has 6 to 60 carbon atoms.
[0052] The terms “aryl group” and “arylene group” used in the present invention have 6 to 60 carbon atoms, respectively, unless otherwise specified, but are not limited thereto. In the present invention, an aryl group or an arylene group means a single ring or multiple ring aromatic, and includes an aromatic ring formed by an adjacent substituent joining or participating in a reaction.
[0053] For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.
[0054] The prefix “aryl” or “ar” means a radical substituted with an aryl group. For example, an arylalkyl may be an alkyl substituted with an aryl, and an arylalkenyl may be an alkenyl substituted with aryl, and a radical substituted with an aryl has a number of carbon atoms as defined herein.
[0055] Also, when prefixes are named subsequently, it means that substituents are listed in the order described first. For example, an arylalkoxy means an alkoxy substituted with an aryl, an alkoxylcarbonyl means a carbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl also means an alkenyl substituted with an arylcarbonyl, wherein the arylcarbonyl may be a carbonyl substituted with an aryl.
[0056] Unless otherwise stated, the term “heterocyclic group”, as used herein, contains one or more heteroatoms, but is not limited thereto, has 2 to 60 carbon atoms, includes any one of a single ring or multiple ring, and may include heteroaliphadic ring and heteroaromatic ring. Also, the heterocyclic group may also be formed in conjunction with an adjacent group.
[0057] Unless otherwise stated, the term “heteroatom”, as used herein, represents at least one of N, O, S, P, or Si.
[0058] Also, the term “heterocyclic group” may include a ring including SO.sub.2 instead of carbon consisting of cycle. For example, “heterocyclic group” includes the following compound.
##STR00002##
[0059] Unless otherwise stated, the term “fluorenyl group” or “fluorenylene group”, as used herein, means a monovalent or divalent functional group, in which R, R′ and R″ are all hydrogen in the following structures, and the term “substituted fluorenyl group” or “substituted fluorenylene group” means that at least one of the substituents R, R′, R″ is a substituent other than hydrogen, and include those in which R and R′ are bonded to each other to form a spiro compound together with the carbon to which they are bonded.
##STR00003##
[0060] The term “spiro compound”, as used herein, has a ‘spiro union’, and a spiro union means a connection in which two rings share only one atom. At this time, atoms shared in the two rings are called ‘spiro atoms’, and these compounds are called ‘monospiro-’, ‘di-spiro-’ and ‘tri-spiro-’, respectively, depending on the number of spiro atoms in a compound.
[0061] Unless otherwise stated, the term “aliphatic”, as used herein, means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the term “aliphatic ring”, as used herein, means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
[0062] Unless otherwise stated, the term “ring”, as used herein, means an aliphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6 to 60 carbon atoms, or a hetero ring having 2 to 60 carbon atoms, or a fused ring formed by the combination of them, and includes a saturated or unsaturated ring.
[0063] Other hetero compounds or hetero radicals other than the above-mentioned hetero compounds include, but are not limited thereto, one or more heteroatoms.
[0064] Also, unless expressly stated, as used herein, “substituted” in the term “substituted or unsubstituted” means substituted with one or more substituents selected from the group consisting of deuterium, halogen, an amino group, a nitrile group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxyl group, a C.sub.1-C.sub.20 alkylamine group, a C.sub.1-C.sub.20 alkylthiopen group, a C.sub.6-C.sub.20 arylthiopen group, a C.sub.2-C.sub.20 alkenyl group, a C.sub.2-C.sub.20 alkynyl group, a C.sub.3-C.sub.20 cycloalkyl group, a C.sub.6-C.sub.20 aryl group, a C.sub.6-C.sub.20 aryl group substituted by deuterium, a C.sub.8-C.sub.20 arylalkenyl group, a silane group, a boron group, a germanium group, and a C.sub.2-C.sub.20 heterocyclic group, but is not limited to these substituents.
[0065] Also, unless there is an explicit explanation, the formula used in the present invention is the same as the definition of the substituent by the exponent definition of the following formula.
##STR00004##
[0066] Here, when a is an integer of zero, the substituent R.sup.1 is absent, when a is an integer of 1, the sole substituent R.sup.1 is linked to any one of the carbon constituting the benzene ring, when a is an integer of 2 or 3, each is bonded as follows, where R.sup.1 may be the same or different from each other, when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted.
##STR00005##
##STR00006##
[0067] Hereinafter, a compound according to an aspect of the present invention and an organic electronic element including the same will be described.
[0068] The present invention provides a compound represented by Formula 1.
##STR00007##
wherein, each symbol may be defined as follows. [0069] 1) X is O or S, [0070] 2) a and b are each independently 0 or 1, provided that a+b is 1 or more, [0071] 3) Ar.sup.1 and Ar.sup.2 are each independently selected from the group consisting of a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; and a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring. [0072] Wherein in case Ar.sup.1 and Ar.sup.2 are an aryl group, it may be preferably a C.sub.6-C.sub.30 aryl group, and more preferably a C.sub.6-C.sub.25 aryl group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, etc. [0073] In case Ar.sup.1 and Ar.sup.2 are a heterocyclic group, it may be preferably a C.sub.2-C.sub.30 heterocyclic group, and more preferably a C.sub.2-C.sub.24 heterocyclic group, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc. [0074] In case Ar.sup.1 and Ar.sup.2 are a fused ring group, it may be preferably a fused ring group of a C.sub.3-C.sub.30 aliphatic ring and a C.sub.6-C.sub.30 aromatic ring, more preferably a fused ring group of a C.sub.3-C.sub.24 aliphatic ring and a C.sub.6-C.sub.24 aromatic ring. [0075] 4) L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5 and L.sup.6 are each independently selected from the group consisting of a single bond; an C.sub.6-C.sub.60 arylene group; a fluorenylene group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; and a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring. [0076] Wherein in case L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5 and L.sup.6 are an arylene group, it may be preferably a C.sub.6-C.sub.30 arylene group, more preferably a C.sub.6-C.sub.24 arylene group, for example, phenylene, biphenyl, naphthalene, terphenyl, etc. [0077] In case L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5 and L.sup.6 are a heterocyclic group, it may be preferably a C.sub.2-C.sub.30 heterocyclic group, and more preferably a C.sub.2-C.sub.24 heterocyclic group, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc. [0078] In case L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5 and L.sup.6 are a fused ring group, it may be preferably a fused ring group of a C.sub.3-C.sub.30 aliphatic ring and a C.sub.6-C.sub.30 aromatic ring, more preferably a fused ring group of a C.sub.3-C.sub.24 aliphatic ring and a C.sub.6-C.sub.24 aromatic ring. [0079] 5) i) In case a is 0, R.sup.1 is independently selected from the group consisting of hydrogen; deuterium; tritium; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxyl group; a C.sub.6-C.sub.60 aryloxy group; a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; or R.sup.1 and R.sup.2 are bonded to each other to form a ring. [0080] Wherein in case R.sup.1 is an alkyl group, it may be preferably a C.sub.1-C.sub.30 alkyl group, and more preferably a C.sub.1-C.sub.24 alkyl group. [0081] In case R.sup.1 is an alkenyl group, they may be preferably an C.sub.2~C.sub.30 alkenyl group, more preferably an C.sub.2~C.sub.24 alkenyl group. [0082] In case R.sup.1 is an alkynyl group, they may be preferably an C.sub.2~C.sub.30 alkynyl group, more preferably an C.sub.2~C.sub.24 alkynyl group. [0083] In case R.sup.1 is an alkoxyl group, it may be preferably a C.sub.1-C.sub.30 alkoxyl group, more preferably an C.sub.1~C.sub.24 alkoxyl group. [0084] In case R.sup.1 is an aryloxy group, it may be preferably a C.sub.6-C.sub.30 aryloxy group, more preferably an C.sub.6~C.sub.24 aryloxy group. [0085] In case R.sup.1 is an aryl group, it may be preferably a C.sub.6-C.sub.30 aryl group, more preferably an C.sub.6~C.sub.25 aryl group. [0086] In case R.sup.1 is a heterocyclic group, it may be preferably a C.sub.2-C.sub.30 heterocyclic group, and more preferably a C.sub.2-C.sub.24 heterocyclic group, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc. [0087] In case R.sup.1 is a fused ring group, it may be preferably a fused ring group of a C.sub.3-C.sub.30 aliphatic ring and a C.sub.6-C.sub.30 aromatic ring, more preferably a fused ring group of a C.sub.3-C.sub.24 aliphatic ring and a C.sub.6-C.sub.24 aromatic ring. [0088] ii) when a is 1, R.sup.1 is Z; wherein Z is selected from the group consisting of a C.sub.6-C.sub.60 arylene group; a fluorenylene group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; or Z and R.sup.2 may be bonded to each other to form a ring. [0089] Wherein in case Z is an arylene group, it may be preferably a C.sub.6-C.sub.30 arylene group, and more preferably a C.sub.6-C.sub.24 arylene group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, etc. [0090] In case Z is a heterocyclic group, it may be preferably a C.sub.2-C.sub.30 heterocyclic group, and more preferably a C.sub.2-C.sub.24 heterocyclic group, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc. [0091] In case Z is a fused ring group, it may be preferably a fused ring group of a C.sub.3-C.sub.30 aliphatic ring and a C.sub.6-C.sub.30 aromatic ring, more preferably a fused ring group of a C.sub.3-C.sub.24 aliphatic ring and a C.sub.6-C.sub.24 aromatic ring. [0092] 6) R.sup.2 is independently selected from the group consisting of hydrogen; deuterium; tritium; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxyl group; a C.sub.6-C.sub.60 aryloxy group; a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring. [0093] Wherein in case R.sup.2 is an alkyl group, it may be preferably a C.sub.1-C.sub.30 alkyl group, and more preferably a C.sub.1-C.sub.24 alkyl group. [0094] In case R.sup.2 is an alkenyl group, they may be preferably an C.sub.2~C.sub.30 alkenyl group, more preferably an C.sub.2~C.sub.24 alkenyl group. [0095] In case R.sup.2 is an alkynyl group, they may be preferably an C.sub.2~C.sub.30 alkynyl group, more preferably an C.sub.2~C.sub.24 alkynyl group. [0096] In case R.sup.2 is an alkoxyl group, it may be preferably a C.sub.1-C.sub.30 alkoxyl group, more preferably an C.sub.1~C.sub.24 alkoxyl group. [0097] In case R.sup.2 is an aryloxy group, it may be preferably a C.sub.6-C.sub.30 aryloxy group, more preferably an C6-C24 aryloxy group. [0098] In case R.sup.2 is an aryl group, it may be preferably a C.sub.6-C.sub.30 aryl group, more preferably an C.sub.6~C.sub.25 aryl group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, etc. [0099] In case R.sup.2 is a heterocyclic group, it may be preferably a C.sub.2-C.sub.30 heterocyclic group, and more preferably a C.sub.2-C.sub.24 heterocyclic group, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc. [0100] In case R.sup.2 is a fused ring group, it may be preferably a fused ring group of a C.sub.3-C.sub.30 aliphatic ring and a C.sub.6-C.sub.30 aromatic ring, more preferably a fused ring group of a C.sub.3-C.sub.24 aliphatic ring and a C.sub.6-C.sub.24 aromatic ring. [0101] 7) R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are independently selected from the group consisting of hydrogen; deuterium; tritium; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxyl group; a C.sub.6-C.sub.60 aryloxy group; a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring, or wherein in case m, n, o, p, q, r, s and t are 2 or more, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are each in plural being the same or different, or a plurality of R.sup.3 or a plurality of R.sup.4 or a plurality of R.sup.5 or a plurality of R.sup.6 or a plurality of R.sup.7 or a plurality of R.sup.10 or a plurality of R.sup.11 or a plurality of R.sup.12 may be bonded to each other to form a ring. [0102] Wherein R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are an alkyl group, it may be preferably a C.sub.1-C.sub.30 alkyl group, and more preferably a C.sub.1-C.sub.24 alkyl group. [0103] In case R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are an alkenyl group, it may be preferably an C.sub.2~C.sub.30 alkenyl group, more preferably an C.sub.2~C.sub.24 alkenyl group. [0104] In case R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are an alkynyl group, it may be preferably an C.sub.2~C.sub.30 alkynyl group, more preferably an C.sub.2~C.sub.24 alkynyl group. [0105] In case R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are an alkoxyl group, it may be preferably a C.sub.1-C.sub.30 alkoxyl group, more preferably an C.sub.1~C.sub.24 alkoxyl group. [0106] In case R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are an aryloxy group, it may be preferably a C.sub.6-C.sub.30 aryloxy group, more preferably an C.sub.6~C.sub.24 aryloxy group. [0107] In case R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are an aryl group, it may be preferably a C.sub.6-C.sub.30 aryl group, more preferably an C.sub.6~C.sub.25 aryl group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, etc. [0108] In case R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are a heterocyclic group, it may be preferably a C.sub.2-C.sub.30 heterocyclic group, and more preferably a C.sub.2-C.sub.24 heterocyclic group, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc. [0109] In case R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are a fused ring group, it may be preferably a fused ring group of a C.sub.3-C.sub.30 aliphatic ring and a C.sub.6-C.sub.30 aromatic ring, more preferably a fused ring group of a C.sub.3-C.sub.24 aliphatic ring and a C.sub.6-C.sub.24 aromatic ring. [0110] 8) R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are may be bonded to each other to form a ring, however, unless R.sup.5 and R.sup.8 or R.sup.9 and R.sup.12 are bonded to each other to form a ring, [0111] 9) m, n, o, p, q, r, s and t are each independently an integer from 0 to 4, [0112] 10) wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C.sub.1-C.sub.20 alkylthio group; C.sub.1-C.sub.20 alkoxyl group; C.sub.1-C.sub.20 alkyl group; C.sub.2-C.sub.20 alkenyl group; C.sub.2-C.sub.20 alkynyl group; C.sub.6-C.sub.20 aryl group; C.sub.6-C.sub.20 aryl group substituted with deuterium; a fluorenyl group; C.sub.2~C.sub.20 heterocyclic group; C.sub.3-C.sub.20 cycloalkyl group; C.sub.7-C.sub.20 arylalkyl group; and C.sub.8-C.sub.20 arylalkenyl group; also the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term ‘ring’ means a C.sub.3-C.sub.60 aliphatic ring or a C.sub.6-C.sub.60 aromatic ring or a C.sub.2-C.sub.60 heterocyclic group or a fused ring formed by the combination thereof.
[0113] Also, Z is represented by any one of Formulas 2-1 to 2-3
##STR00008##
##STR00009##
##STR00010##
In Formulas 2-1 to 2-3, each symbol may be defined as follows. [0114] 1) X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6, X.sup.7, X.sup.8, X.sup.9, X.sup.10, X.sup.11 and X.sup.12, are each independently CR.sup.a or N, [0115] 2) R.sup.a is independently selected from the group consisting of hydrogen; deuterium; tritium; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxyl group; a C.sub.6-C.sub.60 aryloxy group; a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; or a plurality of R.sup.a may be bonded to each other to form a ring. [0116] Wherein in case R.sup.a is an alkyl group, it may be preferably a C.sub.1-C.sub.30 alkyl group, and more preferably a C.sub.1-C.sub.24 alkyl group. [0117] In case R.sup.a is an alkenyl group, they may be preferably an C.sub.2~C.sub.30 alkenyl group, more preferably an C.sub.2~C.sub.24 alkenyl group. [0118] In case R.sup.a is an alkynyl group, they may be preferably an C.sub.2~C.sub.30 alkynyl group, more preferably an C.sub.2~C.sub.24 alkynyl group. [0119] In case R.sup.a is an alkoxyl group, it may be preferably a C.sub.1-C.sub.30 alkoxyl group, more preferably an C.sub.1~C.sub.24 alkoxyl group. [0120] In case R.sup.a is an aryloxy group, it may be preferably a C.sub.6-C.sub.30 aryloxy group, more preferably an C.sub.6~C.sub.24 aryloxy group. [0121] In case R.sup.a is an aryl group, it may be preferably a C.sub.6-C.sub.30 aryl group, more preferably an C.sub.6~C.sub.25 aryl group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, etc. [0122] In case R.sup.a is a heterocyclic group, it may be preferably a C.sub.2-C.sub.30 heterocyclic group, and more preferably a C.sub.2-C.sub.24 heterocyclic group, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc. [0123] In case R.sup.a is a fused ring group, it may be preferably a fused ring group of a C.sub.3-C.sub.30 aliphatic ring and a C.sub.6-C.sub.30 aromatic ring, more preferably a fused ring group of a C.sub.3-C.sub.24 aliphatic ring and a C.sub.6-C.sub.24 aromatic ring. [0124] 3) represents a bonding position.
[0125] Also, Formula 1 is represented by Formula 2 or Formula
##STR00012##
##STR00013##
{wherein, X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, L.sup.6, Ar.sup.1, Ar.sup.2, Z, m, n, o, p, q, r, s and t are the same as defined above.}
[0126] Also, Formula 1 is represented by any one of Formulas 4 to 9. Preferably, Formula 1 is a compound represented by Formula 5, Formula 6, Formula 8, or Formula 9.
##STR00014##
##STR00015##
##STR00016##
##STR00017##
##STR00018##
##STR00019##
{wherein, X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, L.sup.6, Ar.sup.1, Ar.sup.2, Z, m, n, o, p, q, r, s and t are the same as defined above.}
[0127] Also, Formula 1 is represented by any one of Formulas 10 to 13
##STR00020##
##STR00021##
##STR00022##
##STR00023##
{wherein, X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, L.sup.1, L.sup.2, L.sup.3, Ar.sup.1, m, n, o, p, and q are the same as defined above.}
[0128] Also, Ar.sup.1 or Ar.sup.2 is represented by Formula 1-1
##STR00024##
In Formula 1-1, each symbol may be defined as follows. [0129] 1) Y is O, S, NR.sup.b or CR’R″, [0130] 2) R.sup.13, R.sup.14, R.sup.b, R′ and R″ are independently selected from the group consisting of hydrogen; deuterium; tritium; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxyl group; a C.sub.6-C.sub.60 aryloxy group; a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; or, a plurality of adjacent R.sup.13 or a plurality of R.sup.14 or R′ and R″ may be bonded to each other to form a ring. [0131] Wherein in case R.sup.13, R.sup.14, R.sup.b, R′ and R″ are an alkyl group, it may be preferably a C.sub.1-C.sub.30 alkyl group, and more preferably a C.sub.1-C.sub.24 alkyl group. [0132] In case R.sup.13, R.sup.14, R.sup.b, R′ and R″ are an alkenyl group, they may be preferably an C.sub.2~C.sub.30 alkenyl group, more preferably an C.sub.2~C.sub.24 alkenyl group. [0133] In case R.sup.13, R.sup.14, R.sup.b, R′ and R″ are an alkynyl group, they may be preferably an C.sub.2~C.sub.30 alkynyl group, more preferably an C.sub.2~C.sub.24 alkynyl group. [0134] In case R.sup.13, R.sup.14, R.sup.b, R′ and R″ are an alkoxyl group, it may be preferably a C.sub.1-C.sub.30 alkoxyl group, more preferably an C.sub.1~C.sub.24 alkoxyl group. [0135] In case R.sup.13, R.sup.14, R.sup.b, R′ and R″ are an aryloxy group, it may be preferably a C.sub.6-C.sub.30 aryloxy group, more preferably an C.sub.6~C.sub.24 aryloxy group. [0136] In case R.sup.13, R.sup.14, R.sup.b, R′ and R″ are an aryl group, it may be preferably a C.sub.6-C.sub.30 aryl group, more preferably an C.sub.6~C.sub.25 aryl group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, etc. [0137] In case R.sup.13, R.sup.14, R.sup.b, R′ and R″ are a heterocyclic group, it may be preferably a C.sub.2-C.sub.30 heterocyclic group, and more preferably a C.sub.2-C.sub.24 heterocyclic group, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc. [0138] In case R.sup.13, R.sup.14, R.sup.b, R′ and R″ are a fused ring group, it may be preferably a fused ring group of a C.sub.3-C.sub.30 aliphatic ring and a C.sub.6-C.sub.30 aromatic ring, more preferably a fused ring group of a C.sub.3-C.sub.24 aliphatic ring and a C.sub.6-C.sub.24 aromatic ring. [0139] 3) w is an integer of 0 to 3, x is an integer of 0 to 4, [0140] 4) indicates the position to be bonded
[0141] Also, Formula 1 is represented by Formula 14 or Formula 15.
##STR00026##
##STR00027##
{wherein, [0142] 1) X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, L.sup.6, Z, m, n, o, p, q, r, s, t and [0143] 2) Y, R.sup.13, R.sup.14, w and x are the same as defined above.}
[0144] Also, Formula 1 is represented by any one of Formulas 16 to 21, and more preferably represented by Formula 17, Formula 18, Formula 20, or Formula 21.
##STR00028##
##STR00029##
##STR00030##
##STR00031##
##STR00032##
##STR00033##
{wherein, [0145] 1) X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, L.sup.6, Z, m, n, o, p, q, r, s, t and [0146] 2) Y, R.sup.13, R.sup.14, w and x are the same as defined above.}
[0147] Also, Formula 1 is represented by any one of Formulas 22 to 25
##STR00034##
##STR00035##
##STR00036##
##STR00037##
{wherein, [0148] 1) X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, L.sup.1, L.sup.2, L.sup.3, m, n, o, p, q and [0149] 2) Y, R.sup.13, R.sup.14, w and x are the same as defined above.}
[0150] Also, Formula 1-1 is represented by any one of Formulas 1-2 to 1-5.
##STR00038##
##STR00039##
##STR00040##
##STR00041##
{wherein, Y, R.sup.13, R.sup.14, w and x are the same as the definition of Formula 1-1,
##STR00042##
indicates the position to be bonded.}
[0151] Specifically, the compound represented by Formula 1 may be any one of the compounds P1-1 to P7-4, but is not limited thereto.
##STR00043##
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##STR00217##
##STR00218##
##STR00219##
##STR00220##
[0152] Referring to
[0153] The organic material layer may sequentially include a hole injection layer (120), a hole transport layer (130), an emitting layer (140), an electron transport layer (150), and an electron injection layer (160) on the first electrode (110). In this case, the remaining layers except for the emitting layer (140) may not be formed. It may further include a hole blocking layer, an electron blocking layer, an emitting-auxiliary layer (220), a buffer layer (210), etc. and the electron transport layer (150) and the like may serve as a hole blocking layer. (See
[0154] Also, the organic electronic element according to an embodiment of the present invention may further include a protective layer or a light efficiency enhancing layer (180). The light efficiency enhancing layer may be formed on one of both surfaces of the first electrode not in contact with the organic material layer or on one of both surfaces of the second electrode not in contact with the organic material layer. The compound according to an embodiment of the present invention applied to the organic material layer may be used as a host or dopant of the hole injection layer (120), the hole transport layer (130), the emitting-auxiliary layer (220), electron transport auxiliary layer, the electron transport layer (150), and an electron injection layer (160), the emitting layer (140) or as a material for the light efficiency enhancing layer. Preferably, for example, the compound according to Formula 1 of the present invention may be used as a material for a hole transport layer, a host of an emitting layer, and/or an emitting auxiliary layer.
[0155] The organic material layer may include 2 or more stacks including a hole transport layer, an emitting layer and an electron transport layer sequentially formed on the anode, further include a charge generation layer formed between the 2 or more stacks (see
[0156] Otherwise, even with the same core, the band gap, electrical characteristics, interface characteristics, etc. may vary depending on which position the substituent is bonded to, therefore the choice of core and the combination of sub-substituents bound thereto are also very important, and in particular, when the optimal combination of energy levels and T1 values and unique properties of materials(mobility, interfacial characteristics, etc.) of each organic material layer is achieved, a long lifespan and high efficiency can be achieved at the same time.
[0157] The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a PVD (physical vapor deposition) method. For example, depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, and after forming an organic material layer including the hole injection layer(120), the hole transport layer(130), the emitting layer(140), the electron transport layer(150) and the electron injection layer(160) thereon, it can be prepared by depositing a material that can be used as a cathode thereon.
[0158] Also, in the present invention, the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, and a roll-to-roll process, and the organic material layer provides an organic electronic element comprising the compound as an electron transport material.
[0159] As another specific example, the same or different compounds of the compound represented by Formula 1 are mixed and used in the organic material layer.
[0160] Also, the present invention provides a composition for a hole transport layer, an emitting auxiliary layer or an emitting layer comprising the compound represented by Formula 1, and provides an organic electronic element comprising the hole transport layer, the emitting auxiliary layer or the emitting layer.
[0161] Also, the present invention provides an electronic device comprising a display device including the organic electronic element; and a control unit for driving the display device;
[0162] In another aspect, the organic electronic element is at least one of an organic electroluminescent device, an organic solar cell, an organic photo conductor, an organic transistor, and a device for monochromatic or white lighting. At this time, the electronic device may be a current or future wired/wireless communication terminal, and covers all kinds of electronic devices including mobile communication terminals such as mobile phones, a personal digital assistant(PDA), an electronic dictionary, a point-to-multipoint(PMP), a remote controller, a navigation unit, a game player, various kinds of TVs, and various kinds of computers.
[0163] Hereinafter, a synthesis example of the compound represented by Formula 1 of the present invention and a manufacturing example of an organic electronic element of the present invention will be described in detail with reference to Examples, but the present invention is not limited to the following Examples.
Synthesis Example 1
[0164] The compound (final product) represented by Formula 1 according to the present invention is synthesized as shown in Scheme 1 below, but is not limited thereto. Hal.sup.1 and Hal.sup.2 are I, Br or Cl.
##STR00221##
I. Synthesis of Sub 1
[0165] Sub1 of Reaction Scheme 1 is synthesized by the reaction route of Reaction Scheme 2, but is not limited thereto. Hal.sup.1 and Hal.sup.2 are I, Br or Cl. Hal.sup.3 is I or Br.
##STR00222##
##STR00223##
##STR00224##
##STR00225##
##STR00226##
##STR00227##
##STR00228##
Synthesis Example of Sub1-1-a
[0166] 1-bromophenoxy)-2-iodobenzene (50.0 g, 133 mmol) was dissolved in THF (300 mL) in a round-bottom flask under a nitrogen atmosphere, and then cooled to -78° C. Then, n-BuLi (53 mL) is slowly titrated and the mixture is stirred for 30 minutes. Then, propan-2-one (7.7 g, 133 mmol) is dissolved in THF (145 mL) and slowly titrated to the round-bottom flask being reacted. After stirring for an additional 1 hour at -78° C., it is gradually raised to room temperature. When the reaction was completed, the organic layer was extracted with ethyl acetate and water, dried over MgSO.sub.4, concentrated, and the resulting compound was recrystallized by silicagel column to obtain 33.6 g (yield 82%) of the product.
Synthesis Example of Sub1-1
[0167] The obtained Sub1-1-a (33.6 g, 109 mmol), acetic acid (273 mL) and concentrated hydrochloric acid (44 mL) were placed in a round-bottom flask and stirred at 60-80° C. under nitrogen atmosphere for 3 hours. When the reaction was completed, the mixture was extracted with CH.sub.2Cl.sub.2 and water, the organic layer was dried over MgSO.sub.4, concentrated, and the resulting compound was recrystallized using silicagel column to obtain 27.2 g (yield 86%) of the product.
##STR00229##
##STR00230##
##STR00231##
or
##STR00232##
Synthesis Example of Sub1-2-a
[0168] 1-chlorophenoxy)-2-iodobenzene (50.0 g, 151 mmol), n-BuLi (61 mL), and propan-2-one (8.8 g, 151 mmol) were used to obtain 31.8 g of the product (yield 80%) using the Synthesis method of Sub1-1-a.
Synthesis Example of Sub1-2, Sub1-4
[0169] The obtained Sub1-2-a (31.8 g, 121 mmol), acetic acid (300 mL) and concentrated hydrochloric acid (48 mL) were used to obtain 17.5 g (yield: 59%) of Sub1-2 and 7.4 g (yield: 25%) of Sub1-4 by using the Synthesis method of Sub1-1.
##STR00233##
##STR00234##
##STR00235##
Synthesis Example of Sub1-5-a
[0170] 1-bromophenoxy)-2-iodobenzene (25.0 g, 66.7 mmol), n-BuLi (27 mL), benzophenone (12.1 g, 66.7 mmol) were used to obtain 22.4 g of the product (yield 78%) using the Synthesis method of Sub1-1-a.
Synthesis Example of Sub1-5
[0171] The obtained Sub1-5-a (22.4 g, 52.0 mmol), acetic acid (130 mL) and concentrated hydrochloric acid (21 mL) were used to obtain 17.6 g of the product (yield 82%) using the synthesis of Sub1-1.
##STR00236##
##STR00237##
##STR00238##
Synthesis Example of Sub1-12-a
[0172] 1-iodophenoxybenzene (25.0 g, 84.4 mmol), n-BuLi (34 mL), (2-bromophenyl)(phenyl)methanone (22.0 g, 84.4 mmol) were used to obtain 29.5 g of the product (yield 81%) using the Synthesis method of Sub1-1-a.
Synthesis Example of Sub1-12
[0173] The obtained Sub1-12-a (29.5 g, 68.4 mmol), acetic acid (170 mL) and concentrated hydrochloric acid (27 mL) were used to obtain 22.6 g of the product (yield 80%) using the synthesis of Sub1-1.
##STR00239##
##STR00240##
##STR00241##
Synthesis Example of Sub1-13-a
[0174] 1-iodophenoxybenzene (50.0 g, 169 mmol), n-BuLi (68 mL), 2-bromo-9H-fluoren-9-one (43.8 g, 169 mmol) were used to obtain 59.4 g of the product (yield 82%) using the Synthesis method of Sub1-1-a.
Synthesis Example of Sub1-13
[0175] The obtained Sub1-13-a (59.4 g, 138 mmol), acetic acid (345 mL) and concentrated hydrochloric acid (55 mL) were used to obtain 47.3 g of the product (yield 83%) using the synthesis of Sub1-1.
##STR00242##
##STR00243##
##STR00244##
After dissolving Sub1-2 (5.0 g, 20.4 mmol) in THF (102 mL), (5-bromo-[1,1′-biphenyl]-3-yl)boronic acid (5.7 g, 20.4 mmol), NaOH (2.5 g, 61.3 mmol), Pd(PPh.sub.3).sub.4 (1.42 g, 1.23 mmol) and Water (51 mL) were added and stirred at 80° C. When the reaction was completed, the mixture was extracted with CH.sub.2CI.sub.2 and water, and the organic layer was dried over MgSO.sub.4 and concentrated.
[0176] Thereafter, the resulting compound was recrystallized after applying a silica gel column to obtain 6.6 g (yield 71%) of the product.
##STR00245##
##STR00246##
##STR00247##
Synthesis Example of Sub1-20-a
[0177] bromophenyl)(2-iodophenyl)sulfane (50.0 g, 128 mmol), n-BuLi (51 mL), propan-2-one (7.4 g, 128 mmol) were used to obtain 34.3 g of the product (yield 83%) using the Synthesis method of Sub1-1-a.
Synthesis Example of Sub1-20
[0178] The obtained Sub1-20-a (34.3 g, 106 mmol), acetic acid (265 mL) and concentrated hydrochloric acid (42 mL) were used to obtain 26.2 g of the product (yield 81%) using the synthesis of Sub1-1
##STR00248##
##STR00249##
##STR00250##
or
##STR00251##
Synthesis Example of Sub1-21-a
[0179] chlorophenyl)(2-iodophenyl)sulfane (50.0 g, 144 mmol), n-BuLi (58 mL), propan-2-one (8.4 g, 144 mmol) were used to obtain 32.3 g of the product (yield 80%) using the Synthesis method of Sub1-1-a.
Synthesis Example of Sub1-21
[0180] The obtained Sub1-21-a (32.2 g, 115 mmol), acetic acid (290 mL) and concentrated hydrochloric acid (46 mL) was used to obtain 17.2 g of Sub1-21 (yield 57%) and 7.5 g (yield of 25%) of Sub1-23 by using the method for Sub1-1.
##STR00252##
##STR00253##
##STR00254##
Synthesis Example of Sub1-25-a
[0181] bromophenyl)(2-iodophenyl)sulfane (30.0 g, 76.7 mmol), n-BuLi (31 mL), benzophenone (14.0 g, 76.7 mmol) were used to obtain 28.1 g of the product (yield 82%) using the Synthesis method of Sub1-1-a.
Synthesis Example of Sub1-25
[0182] The obtained Sub1-25-a (28.1 g, 62.9 mmol), acetic acid (157 mL) and concentrated hydrochloric acid (25 mL) were used to obtain 23.0 g of the product (yield 85%) using the synthesis of Sub1-1
##STR00255##
##STR00256##
##STR00257##
Synthesis Example of Sub1-29-a
[0183] bromophenyl)(2-iodophenyl)sulfane (50.0 g, 128 mmol), n-BuLi (51 mL), 9H-fluoren-9-one (23.0 g, 128 mmol) were used to obtain 46.7 g of the product (yield 82%) using the Synthesis method of Sub1-1-a.
Synthesis Example of Sub1-29
[0184] The obtained Sub1-29-a (46.7 g, 105 mmol), acetic acid (262 mL) and concentrated hydrochloric acid (42 mL) were used to obtain 36.3 g of the product (yield 81%) using the synthesis of Sub1-1
##STR00258##
##STR00259##
##STR00260##
##STR00261##
Synthesis Example of Sub1-34-a
[0185] iodophenyl)(phenyl)sulfane (25.0 g, 80.1 mmol), n-BuLi (32 mL), (3-bromophenyl)(phenyl)methanone (20.9 g, 80.1 mmol) were used to obtain 27.9 g of the product (yield 78%) using the Synthesis method of Sub1-1-a.
Synthesis Example of Sub1-34
[0186] The obtained Sub1-34-a (27.9 g, 62.5 mmol), acetic acid (156 mL) and concentrated hydrochloric acid (25 mL) were used to obtain 22.0 g of the product (yield 82%) using the synthesis of Sub1-1
##STR00262##
##STR00263##
##STR00264##
##STR00265##
Synthesis Example of Sub1-50-a
[0187] 1-bromophenoxy)-2-iodobenzene (5.0 g, 13.3 mmol), n-BuLi (5 mL), (4-chlorophenyl)(phenyl)methanone (2.9 g, 13.3 mmol) were used to obtain 4.9 g of the product (yield 79%) using the Synthesis method of Sub1-1-a.
Synthesis Example of Sub1-50
[0188] The obtained Sub1-50-a (4.9 g, 10.5 mmol), acetic acid (26 mL) and concentrated hydrochloric acid (4 mL) were used to obtain 3.7 g of the product (yield 78%) using the synthesis of Sub1-1
[0189] The compound belonging to Sub1 may be a compound as follows, but is not limited thereto, Table 1 below shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub1.
##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##
TABLE-US-00001 compound FD-MS compound FD-MS Sub1-1 m/z=288.01 (C.sub.15H.sub.13BrO=289.17) Sub1-2 m/z=244.07(C.sub.1.sub.5H.sub.1.sub.3CIO=244.72) Sub1-3 m/z=288.01 (C.sub.15H.sub.13BrO=289.17) Sub1-4 m/z=244.07(C.sub.1.sub.5H.sub.1.sub.3CIO=244.72) Sub1-5 m/z=412.05(C.sub.25H.sub.17BrO=413.31) Sub1-6 m/z=368.10(C.sub.25H.sub.17CIO=368.86) Sub1-7 m/z=410.03(C.sub.25H.sub.15BrO=411.30) Sub1-8 m/z=366.08(C.sub.25H.sub.1.sub.5CIO=366.84) Sub1-9 m/z=410.03(C.sub.25H.sub.15BrO=411.30) Sub1-10 m/z=412.05(C.sub.25H.sub.1.sub.7BrO=413.31) Sub1-11 m/z=412.05(C.sub.25H.sub.17BrO=413.31) Sub1-12 m/z=412.05(C.sub.25H.sub.1.sub.7BrO=413.31) Sub1-13 m/z=410.03(C.sub.25H.sub.15BrO=411.30) Sub1-14 m/z=410.03(C.sub.25H.sub.15BrO=411.30) Sub1-15 m/z=410.03(C.sub.25H.sub.15BrO=411.30) Sub1-16 m/z=364.05(C.sub.21H.sub.1.sub.7BrO=365.27) Sub1-17 m/z=364.05(C.sub.21H.sub.17BrO=365.27) Sub1-18 m/z=440.08(C.sub.27H.sub.21BrO=441.37) Sub1-19 m/z=364.05(C.sub.21H.sub.17BrO=365.27) Sub1-20 m/z=303.99(C.sub.15H.sub.13BrS=305.23) Sub1-21 m/z=260.04(C.sub.1.sub.5H.sub.1.sub.3CIS=260.78) Sub1-22 m/z=303.99(C.sub.15H.sub.13BrS=305.23) Sub1-23 m/z=260.04(C.sub.1.sub.5H.sub.1.sub.3CIS=260.78) Sub1-24 m/z=336.07(C.sub.21H.sub.1.sub.7ClS=336.88) Sub1-25 m/z=428.02(C.sub.25H.sub.17BrS=429.38) Sub1-26 m/z=504.05(C.sub.31H.sub.21 BrS=505.47) Sub1-27 m/z=446.01(C.sub.25H.sub.16BrFS=447.37) Sub1-28 m/z=384.07(C.sub.25H.sub.1.sub.7CIS=384.92) Sub1-29 m/z=428.02(C.sub.25H.sub.17BrS=429.38) Sub1-30 m/z=426.01 (C.sub.25H.sub.15BrS=427.36) Sub1-31 m/z=502.04(C.sub.31H.sub.19BrS=503.46) Sub1-32 m/z=382.06(C.sub.25H.sub.1.sub.5ClS=382.91) Sub1-33 m/z=426.01 (C.sub.25H.sub.15BrS=427.36) Sub1-34 m/z=428.02(C.sub.25H.sub.1.sub.7BrS=429.38) Sub1-35 m/z=428.02(C.sub.25H.sub.17BrS=429.38) Sub1-36 m/z=426.01 (C.sub.25H.sub.15BrS=427.36) Sub1-37 m/z=426.01 (C.sub.25H.sub.15BrS=427.36) Sub1-38 m/z=426.01 (C.sub.25H.sub.15BrS=427.36) Sub1-39 m/z=380.02(C.sub.21H.sub.17BrS=381.33) Sub1-40 m/z=380.02(C.sub.21H.sub.17BrS=381.33) Sub1-41 m/z=380.02(C.sub.21H.sub.17BrS=381.33) Sub1-42 m/z=380.02(C.sub.21H.sub.17BrS=381.33) Sub1-43 m/z=380.02(C.sub.21H.sub.17BrS=381.33) Sub1-44 m/z=504.05(C.sub.31H.sub.21BrS=505.47) Sub1-45 m/z=502.04(C.sub.31H.sub.19BrS=503.46) Sub1-46 m/z=364.05(C.sub.21H.sub.1.sub.7BrO=365.27) Sub1-47 m/z=488.08(C.sub.31H.sub.21BrO=489.41) Sub1-48 m/z=446.01 (C.sub.25H.sub.16BrClO= 447.76) Sub1-49 m/z=459.97(C.sub.25H.sub.14BrClS= 461.80) Sub1-50 m/z=446.01 (C.sub.25H.sub.16BrClO= 447.76) Sub1-51 m/z=446.01 (C.sub.25H.sub.16BrClO= 447.76)
II. Synthesis of Sub2
[0190] Sub2 of Reaction Scheme 1 is synthesized by the reaction route of Reaction Scheme 3, but is not limited thereto. Hal.sup.4 is I, Br or Cl.
##STR00317##
##STR00318##
##STR00319##
##STR00320##
##STR00321##
##STR00322##
9-(4-bromophenyl)-9-phenyl-9H-fluorene (30.0 g, 75.5 mmol) was dissolved in toluene (380 mL) in a round-bottom flask, aniline (7.0 g, 75.5 mmol), Pd.sub.2(dba).sub.3 (2.07 g, 2.27 mmol), P(t-Bu).sub.3 (0.92 g, 4.53 mmol), NaOt—Bu (14.5 g, 151 mmol) were added thereto, and the mixture was stirred at 60° C. When the reaction was completed, the mixture was extracted with CH.sub.2Cl.sub.2 and water, the organic layer was dried over MgSO.sub.4, concentrated, and the resulting compound was recrystallized using silicagel column to obtain 23.2 g (yield 75%) of the product.
##STR00323##
##STR00324##
##STR00325##
9-(3-bromophenyl)-9-phenyl-9H-fluorene (30.0 g, 75.5 mmol), [1,1′-biphenyl]-4-amine (12.8 g, 75.5 mmol), Pd.sub.2(dba).sub.3 (2.07 g, 2.27 mmol), P(t-Bu).sub.3 (0.92 g, 4.53 mmol) and NaOt—Bu (14.5 g, 151 mmol) were used to obtain 26.8 g (yield 73%) of the product using the synthesis method of Sub2-1
##STR00326##
##STR00327##
##STR00328##
9-(2-bromophenyl)-9-phenyl-9H-fluorene (5.0 g, 12.6 mmol), [1,1′-biphenyl]-3-amine (2.1 g, 12.6 mmol), Pd.sub.2(dba).sub.3 (0.35 g, 0.38 mmol), P(t-Bu).sub.3 (0.15 g, 0.76 mmol), NaOt—Bu (2.4 g, 25.2 mmol) were used to obtain 4.2 g (yield 68%) of the product using the synthesis method of Sub2-1
##STR00329##
##STR00330##
##STR00331##
9-(4-bromophenyl)-9-phenyl-9H-fluorene (5.0 g, 12.6 mmol), 9,9-dimethyl-9H-fluoren-2-amine (2.6 g, 12.6 mmol), Pd.sub.2(dba).sub.3 (0.35 g, 0.38 mmol), P(t-Bu).sub.3 (0.15 g, 0.76 mmol), NaOt—Bu (2.4 g, 25.2 mmol) were used to obtain 4.9 g (yield 74%) of the product using the synthesis method of Sub2-1
##STR00332##
##STR00333##
##STR00334##
9-(3-bromophenyl)-9-phenyl-9H-fluorene (5.0 g, 12.6 mmol), dibenzo[b,d]thiophen-3-amine (2.5 g, 12.6 mmol), Pd.sub.2(dba).sub.3 (0.35 g, 0.38 mmol), P(t-Bu).sub.3 (0.15 g, 0.76 mmol), NaOt—Bu (2.4 g, 25.2 mmol) were used to obtain 4.7 g (yield 73%) of the product using the synthesis method of Sub2-1
##STR00335##
##STR00336##
##STR00337##
9-(3-bromophenyl)-9-phenyl-9H-fluorene (5.0 g, 12.6 mmol), naphtho[2,3-b]benzofuran-3-amine (2.9 g, 12.6 mmol), Pd.sub.2(dba).sub.3 (0.35 g, 0.38 mmol), P(t-Bu).sub.3 (0.15 g, 0.76 mmol), NaOt—Bu (2.4 g, 25.2 mmol) were used to obtain 4.9 g (yield 71%) of the product using the synthesis method of Sub2-1
##STR00338##
##STR00339##
##STR00340##
9-(3-bromophenyl)-9-phenyl-9H-fluorene (5.0 g, 12.6 mmol), dibenzo[b,d]furan-2-amine (2.3 g, 12.6 mmol), Pd.sub.2(dba).sub.3 (0.35 g, 0.38 mmol), P(t—Bu).sub.3 (0.15 g, 0.76 mmol), NaOt—Bu (2.4 g, 25.2 mmol) were used to obtain 4.6 g (yield 73%) of the product using the synthesis method of Sub2-1
##STR00341##
##STR00342##
##STR00343##
9-(3-bromophenyl)-9-phenyl-9H-fluorene (5.0 g, 12.6 mmol), 9,9-dimethyl-9H-fluoren-2-amine (2.6 g, 12.6 mmol), Pd.sub.2(dba).sub.3 (0.35 g, 0.38 mmol), P(t—Bu).sub.3 (0.15 g, 0.76 mmol), NaOt—Bu (2.4 g, 25.2 mmol) were used to obtain 4.6 g (yield 70%) of the product using the synthesis method of Sub2-1
##STR00344##
##STR00345##
##STR00346##
9-(2-bromophenyl)-9-phenyl-9H-fluorene (5.0 g, 12.6 mmol), 5-phenyl-5H-benzo[b]carbazol-3-amine (3.9 g, 12.6 mmol), Pd.sub.2(dba).sub.3 (0.35 g, 0.38 mmol), P(t-Bu).sub.3 (0.15 g, 0.76 mmol), NaOt—Bu (2.4 g, 25.2 mmol) were used to obtain 5.1 g (yield 65%) of the product using the synthesis method of Sub2-1
##STR00347##
##STR00348##
##STR00349##
9-(3-bromophenyl)-9-methyl-9H-fluorene (2.0 g, 6.0 mmol), [1,1′-biphenyl]-4-amine (1.0 g, 6.0 mmol), Pd.sub.2(dba).sub.3 (0.16 g, 0.18 mmol), P(t-Bu).sub.3 (0.07 g, 0.36 mmol), NaOt—Bu (1.1 g, 11.9 mmol) were used to obtain 1.8 g (yield 71%) of the product using the synthesis method of Sub2-1
[0191] The compound belonging to Sub 2 may be a compound as follows, but is not limited thereto, Table 2 shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub 2.
##STR00350##
##STR00351##
##STR00352##
##STR00353##
##STR00354##
##STR00355##
##STR00356##
##STR00357##
##STR00358##
##STR00359##
##STR00360##
##STR00361##
##STR00362##
##STR00363##
##STR00364##
##STR00365##
##STR00366##
##STR00367##
##STR00368##
##STR00369##
##STR00370##
##STR00371##
##STR00372##
##STR00373##
##STR00374##
##STR00375##
##STR00376##
##STR00377##
##STR00378##
##STR00379##
##STR00380##
##STR00381##
##STR00382##
##STR00383##
##STR00384##
##STR00385##
##STR00386##
##STR00387##
##STR00388##
##STR00389##
##STR00390##
##STR00391##
##STR00392##
##STR00393##
##STR00394##
##STR00395##
##STR00396##
##STR00397##
##STR00398##
##STR00399##
##STR00400##
##STR00401##
##STR00402##
##STR00403##
##STR00404##
##STR00405##
##STR00406##
##STR00407##
##STR00408##
##STR00409##
##STR00410##
##STR00411##
##STR00412##
##STR00413##
##STR00414##
##STR00415##
##STR00416##
##STR00417##
##STR00418##
##STR00419##
##STR00420##
##STR00421##
##STR00422##
##STR00423##
##STR00424##
##STR00425##
##STR00426##
##STR00427##
##STR00428##
##STR00429##
##STR00430##
##STR00431##
##STR00432##
##STR00433##
##STR00434##
##STR00435##
##STR00436##
##STR00437##
##STR00438##
##STR00439##
##STR00440##
##STR00441##
##STR00442##
##STR00443##
##STR00444##
##STR00445##
##STR00446##
##STR00447##
##STR00448##
##STR00449##
##STR00450##
##STR00451##
##STR00452##
##STR00453##
##STR00454##
##STR00455##
##STR00456##
##STR00457##
##STR00458##
##STR00459##
##STR00460##
TABLE-US-00002 comp FD-MS comp FD-MS Sub2-1 m/z=409.18(C.sub.31H.sub.23N=409.53) Sub2 -2 m/z=485.21 (C.sub.37H.sub.27N=485.63) Sub2-3 m/z=485.21 (C.sub.37H.sub.27N=485.63) Sub2 -4 m/z=414.21 (C.sub.31H.sub.1.sub.8D.sub.5N=414.56 ) Sub2-5 m/z=427.17(C.sub.31H.sub.22FN=427.52) Sub2 -6 m/z=434.18(C.sub.32H.sub.22N.sub.2=434.54) Sub2-7 m/z=481.24(C.sub.35H.sub.31NO=481.64) Sub2 -8 m/z=427.17(C.sub.31 H.sub.22FN=427.52) Sub2-9 m/z=486.21 (C.sub.36H.sub.26N.sub.2=486.62) Sub2 -10 m/z=459.20(C.sub.35H.sub.25N=459.59) Sub2-11 m/z=485.21 (C.sub.37H.sub.27N=485.63) Sub2 -12 m/z=503.20(C.sub.37H.sub.26FN=503.62) Sub2-13 m/z=485.21 (C.sub.37H.sub.27N=485.63) Sub2 -14 m/z=409.18(C.sub.31H.sub.23N=409.53) Sub2-15 m/z=485.21 (C.sub.37H.sub.27N=485.63) Sub2 -16 m/z=485.21 (C.sub.37H.sub.27N=485.63) Sub2-17 m/z=485.21 (C.sub.37H.sub.27N=485.63) Sub2 -18 m/z=459.20(C.sub.35H.sub.25N=459.59) Sub2-19 m/z=459.20(C.sub.35H.sub.25N=459.59) Sub2 -20 m/z=485.21 (C.sub.37H.sub.27N=485.63) Sub2-21 m/z=414.21 (C.sub.31H.sub.18D.sub.5N=414.56) Sub2 -22 m/z=427.17(C.sub.31H.sub.22FN=427.52) Sub2-23 m/z=434.18(C.sub.32H.sub.22N.sub.2=434.54) Sub2 -24 m/z=501.21 (C.sub.37H.sub.27NO=501.63) Sub2-25 m/z=459.20(C.sub.35H.sub.25N=459.59) Sub2 -26 m/z=459.20(C.sub.35H.sub.25N=459.59) Sub2- m/z=477.19(C.sub.35H.sub.24FN=477.58) Sub2 m/z=535.23(C.sub.41H.sub.29N=535.69) 27 -28 Sub2-29 m/z=485.21 (C.sub.37H.sub.27N=485.63) Sub2 -30 m/z=485.21 (C.sub.37H.sub.27N=485.63) Sub2-31 m/z=485.21 (C.sub.37H.sub.27N=485.63) Sub2 -32 m/z=409.18(C.sub.31H.sub.23N=409.53) Sub2-33 m/z=485.21 (C.sub.37H.sub.27N=485.63) Sub2 -34 m/z=485.21 (C.sub.37H.sub.27N=485.63) Sub2-35 m/z=459.20(C.sub.35H.sub.25N=459.59) Sub2 -36 m/z=459.20(C.sub.35H.sub.25N=459.59) Sub2-37 m/z=414.21 (C.sub.31H.sub.18D.sub.5N=414.56) Sub2 -38 m/z=427.17(C.sub.31H.sub.22FN=427.52) Sub2-39 m/z=486.21 (C.sub.36H.sub.26N.sub.2=486.62) Sub2 -40 m/z=459.20(C.sub.35H.sub.25N=459.59) Sub2-41 m/z=459.20(C.sub.35H.sub.25N=459.59) Sub2 -42 m/z=535.23(C.sub.41H.sub.29N=535.69) Sub2-43 m/z=485.21 (C.sub.37H.sub.27N=485.63) Sub2 -44 m/z=535.23(C.sub.41H.sub.29N=535.69) Sub2-45 m/z=535.23(C.sub.41H.sub.29N=535.69) Sub2 -46 m/z=509.21 (C.sub.39H.sub.27N=509.65) Sub2-47 m/z=515.17(C.sub.37H.sub.25NS=515.67) Sub2 -48 m/z=515.17(C.sub.37H.sub.25NS=515.67) Sub2-49 m/z=592.2(C.sub.42H.sub.2SN.sub.2S=592.76) Sub2 -50 m/z=583.18(C.sub.41H.sub.26FNS=583.72) Sub2-51 m/z=499.19(C.sub.37H.sub.25NO=499.61) Sub2 -52 m/z=499.19(C.sub.37H.sub.25NO=499.61) Sub2-53 m/z=503.22(C.sub.37H.sub.21D.sub.4NO=503.64 ) Sub2 -54 m/z=575.22(C.sub.43H.sub.29NO=575.71) Sub2- m/z=549.21(C.sub.41H.sub.27NO=549.67) Sub2 m/z=525.25(C.sub.40H.sub.31N=525.70) 55 -56 Sub2-57 m/z=647.26(C.sub.50H.sub.33N=647.82) Sub2 -58 m/z=574.24(C.sub.43H.sub.30N.sub.2=574.73) Sub2-59 m/z=624.26(C.sub.47H.sub.32N.sub.2=624.79) Sub2 -60 m/z=515.17(C.sub.37H.sub.25NS=515.67) Sub2-61 m/z=515.17(C.sub.37H.sub.25NS=515.67) Sub2 -62 m/z=515.17(C.sub.37H.sub.25NS=515.67) Sub2-63 m/z=515.17(C.sub.37H.sub.25NS=515.67) Sub2 -64 m/z=591.20(C.sub.43H.sub.29NS=591.77) Sub2-65 m/z=565.19(C.sub.41H.sub.27NS=565.73) Sub2 -66 m/z=499.19(C.sub.37H.sub.25NO=499.61) Sub2-67 m/z=499.19(C.sub.37H.sub.25NO=499.61) Sub2 -68 m/z=499.19(C.sub.37H.sub.25NO=499.61) Sub2-69 m/z=499.19(C.sub.37H.sub.25NO=499.61) Sub2 -70 m/z=575.22(C.sub.43H.sub.29NO=575.71) Sub2-71 m/z=549.21 (C.sub.41H.sub.27NO=549.67) Sub2 -72 m/z=574.24(C.sub.43H.sub.30N.sub.2=574.73) Sub2-73 m/z=574.24(C.sub.43H.sub.30N.sub.2=574.73) Sub2 -74 m/z=574.24(C.sub.43H.sub.30N.sub.2=574.73) Sub2-75 m/z=624.26(C.sub.47H.sub.32N.sub.2=624.79) Sub2 -76 m/z=525.25(C.sub.40H.sub.31N=525.70) Sub2-77 m/z=525.25(C.sub.40H.sub.31N=525.70) Sub2 -78 m/z=525.25(C.sub.40H.sub.31N=525.70) Sub2-79 m/z=649.28(C.sub.50H.sub.3SN=649.84) Sub2 -80 m/z=647.26(C.sub.50H.sub.33N=647.82) Sub2-81 m/z=601.28(C.sub.46H.sub.35N=601.79) Sub2 -82 m/z=575.26(C.sub.44H.sub.33N=575.76) Sub2- m/z=499.19(C.sub.37H.sub.25NO=499.61) Sub2 m/z=575.22(C.sub.43H.sub.29NO=575.71) 83 -84 Sub2-85 m/z=575.22(C.sub.43H.sub.29NO=575.71) Sub2 -86 m/z=549.21 (C.sub.41H.sub.27NO=549.67) Sub2-87 m/z=515.17(C.sub.37H.sub.25NS=515.67) Sub2 -88 m/z=515.17(C.sub.37H.sub.25NS=515.67) Sub2-89 m/z=515.17(C.sub.37H.sub.25NS=515.67) Sub2 -90 m/z=515.17(C.sub.37H.sub.25NS=515.67) Sub2-91 m/z=525.25(C.sub.40H.sub.31 N=525.70) Sub2 -92 m/z=649.28(C.sub.50H.sub.35N=649.84) Sub2-93 m/z=647.26(C.sub.50H.sub.33N=647.82) Sub2 -94 m/z=624.26(C.sub.47H.sub.32N.sub.2=624.79) Sub2-95 m/z=624.26(C.sub.47H.sub.32N.sub.2=624.79) Sub2 -96 m/z=575.22(C.sub.43H.sub.29NO=575.71) Sub2-97 m/z=650.27(C.sub.49H.sub.34N.sub.2=650.83) Sub2 -98 m/z=601.28(C.sub.46H.sub.35N=601.79) Sub2-99 m/z=593.22(C.sub.43H.sub.28FNO=593.70) Sub2 -100 m/z=601.28(C.sub.46H.sub.35N=601.79) Sub2-101 m/z=667.23(C.sub.49H.sub.33NS=667.87) Sub2 -102 m/z=601.28(C.sub.46H.sub.35N=601.79) Sub2-103 m/z=423.20(C.sub.32H.sub.25N=423.56) Sub2 -104 m/z=347.17(C.sub.26H.sub.21 N=347.46) Sub2-105 m/z=423.20(C.sub.32H.sub.25N=423.56) Sub2 -106 m/z=423.20(C.sub.32H.sub.25N=423.56) Sub2-107 m/z=539.26(C.sub.41H.sub.33N=539.72) Sub2 -108 m/z=487.19(C.sub.36H.sub.25NO=487.60) Sub2-109 m/z=347.17(C.sub.26H.sub.21N=347.46) Sub2 -110 m/z=513.21 (C.sub.38H.sub.27NO=513.64) Sub2-111 m/z=453.16(C.sub.32H.sub.23NS=453.60)
III. Synthesis of Final Product
[0192] ##STR00461##
##STR00462##
##STR00463##
After dissolving Sub1-1 (2.0 g, 6.9 mmol) in toluene (35 mL) in a round-bottom flask, Sub2-2 (3.4 g, 6.9 mmol), Pd.sub.2(dba).sub.3 (0.19 g, 0.21 mmol), P(t-Bu).sub.3 (0.08 g, 0.41 mmol), NaOt—Bu (1.3 g, 13.8 mmol) were added and refluxed. When the reaction was completed, the mixture was extracted with CH.sub.2CI.sub.2 and water, the organic layer was dried over MgSO.sub.4, concentrated, and the resulting compound was recrystallized using silicagel column to obtain 3.5 g (yield 72%) of the product.
##STR00464##
##STR00465##
##STR00466##
Sub1-18 (2.0 g, 4.5 mmol), Sub2-1 (1.9 g, 4.5 mmol), Pd.sub.2(dba).sub.3 (0.12 g, 0.14 mmol), P(t-Bu).sub.3 (0.06 g, 0.27 mmol), NaOt—Bu (0.9 g, 9.1 mmol) were used to obtain 2.6 g (yield 74%) of the product using the synthesis method of P1-1
##STR00467##
##STR00468##
##STR00469##
Sub1-5 (2.0 g, 4.8 mmol), Sub2-14 (2.0 g, 4.8 mmol), Pd.sub.2(dba).sub.3 (0.13 g, 0.15 mmol), P(t-Bu).sub.3 (0.06 g, 0.29 mmol), NaOt—Bu (0.9 g, 9.7 mmol) were used to obtain 2.6 g (yield 72%) of the product using the synthesis method of P1-1
##STR00470##
##STR00471##
##STR00472##
Sub1-13 (2.0 g, 4.9 mmol), Sub2-15 (2.4 g, 4.9 mmol), Pd.sub.2(dba).sub.3 (0.13 g, 0.15 mmol), P(t-Bu).sub.3 (0.06 g, 0.29 mmol), NaOt—Bu (0.9 g, 9.7 mmol) were used to obtain 2.8 g (yield 70%) of the product using the synthesis method of P1-1
##STR00473##
##STR00474##
##STR00475##
Sub1-25 (2.0 g, 4.7 mmol), Sub2-16 (2.3 g, 4.7 mmol), Pd.sub.2(dba).sub.3 (0.13 g, 0.14 mmol), P(t-Bu).sub.3 (0.06 g, 0.28 mmol), NaOt—Bu (0.9 g, 9.3 mmol) were used to obtain 2.8 g (yield 72%) of the product using the synthesis method of P1-1
##STR00476##
##STR00477##
##STR00478##
Sub1-7 (1.8 g, 4.4 mmol), Sub2-105 (1.9 g, 4.4 mmol), Pd.sub.2(dba).sub.3 (0.12 g, 0.13 mmol), P(t-Bu).sub.3 (0.05 g, 0.26 mmol), NaOt—Bu (0.8 g, 8.8 mmol) were used to obtain 2.4 g (yield 73%) of the product using the synthesis method of P1-1
##STR00479##
##STR00480##
##STR00481##
Sub1-12 (2.0 g, 4.8 mmol), Sub2-32 (2.0 g, 4.8 mmol), Pd.sub.2(dba).sub.3 (0.13 g, 0.15 mmol), P(t-Bu).sub.3 (0.06 g, 0.29 mmol), NaOt—Bu (0.9 g, 9.7 mmol) were used to obtain 2.1 g (yield 58%) of the product using the synthesis method of P1-1
##STR00482##
##STR00483##
##STR00484##
Sub1-20 (2.0 g, 6.6 mmol), Sub2-34 (3.2 g, 6.6 mmol), Pd.sub.2(dba).sub.3 (0.18 g, 0.20 mmol), P(t-Bu).sub.3 (0.08 g, 0.39 mmol), NaOt—Bu (1.3 g, 13.1 mmol) were used to obtain 2.9 g (yield 62%) of the product using the synthesis method of P1-1
##STR00485##
##STR00486##
##STR00487##
##STR00488##
Sub1-21 (2.0 g, 7.7 mmol), Sub2-56 (4.0 g, 7.7 mmol), Pd.sub.2(dba).sub.3 (0.21 g, 0.23 mmol), P(i-Bu).sub.3 (0.09 g, 0.46 mmol), NaOt—Bu (1.5 g, 15.3 mmol) were used to obtain 4.3 g (yield 75%) of the product using the synthesis method of P1-1
##STR00489##
##STR00490##
##STR00491##
Sub1-1 (2.0 g, 6.9 mmol), Sub2-76 (3.6 g, 6.9 mmol), Pd.sub.2(dba).sub.3 (0.19 g, 0.21 mmol), P(t-Bu).sub.3 (0.08 g, 0.41 mmol), NaOt—Bu (1.3 g, 13.8 mmol) were used to obtain 3.6 g (yield 71%) of the product using the synthesis method of P1-1
##STR00492##
##STR00493##
##STR00494##
Sub1-29 (2.0 g, 4.7 mmol), Sub2-67 (2.3 g, 4.7 mmol), Pd.sub.2(dba).sub.3 (0.13 g, 0.14 mmol), P(t-Bu).sub.3 (0.06 g, 0.28 mmol), NaOt—Bu (0.9 g, 9.4 mmol) were used to obtain 3.0 g (yield 75%) of the product using the synthesis method of P1-1
##STR00495##
##STR00496##
##STR00497##
##STR00498##
Sub1-34 (2.0 g, 4.7 mmol), Sub2-65 (2.6 g, 4.7 mmol), Pd.sub.2(dba).sub.3 (0.13 g, 0.14 mmol), P(t-Bu).sub.3 (0.06 g, 0.28 mmol), NaOt—Bu (0.9 g, 9.3 mmol) were used to obtain 3.1 g (yield 72%) of the product using the synthesis method of P1-1
##STR00499##
##STR00500##
##STR00501##
Sub1-23 (1.5 g, 5.8 mmol), Sub2-85 (3.3 g, 5.8 mmol), Pd.sub.2(dba).sub.3 (0.16 g, 0.17 mmol), P(t-Bu).sub.3 (0.07 g, 0.35 mmol), NaOt—Bu (1.1 g, 11.5 mmol) were used to obtain 2.4 g (yield 52%) of the product using the synthesis method of P1-1
##STR00502##
##STR00503##
##STR00504##
##STR00505##
##STR00506##
Synthesis Example of Inter7-3
[0193] After dissolving Sub1-50 (1.5 g, 3.4 mmol) with toluene (17 mL) in a round-bottom flask, Sub2-60 (1.7 g, 3.4 mmol), Pd.sub.2(dba).sub.3 (0.09 g, 0.10 mmol), P(t-Bu).sub.3 (0.04 g, 0.20 mmol), NaOt—Bu (0.6 g, 6.7 mmol) was added and stirred at 60° C. When the reaction was completed, the mixture was extracted with CH.sub.2CI.sub.2 and water, the organic layer was dried over MgSO.sub.4, concentrated, and the resulting compound was recrystallized using silicagel column to obtain 2.1 g (yield 72%) of the product.
Synthesis Example of P7-3
[0194] After dissolving Inter7-3 (2.1 g, 2.4 mmol) in toluene (12 mL) in a round-bottom flask, Sub2-2 (1.2 g, 2.4 mmol), Pd.sub.2(dba).sub.3 (0.07 g, 0.07 mmol), P(t-Bu).sub.3 (0.03 g, 0.14 mmol), NaOt—Bu (0.5 g, 4.8 mmol) was added and refluxed. When the reaction was completed, the mixture was extracted with CH.sub.2CI.sub.2 and water, the organic layer was dried over MgSO.sub.4, concentrated, and the resulting compound was recrystallized using silicagel column to obtain 2.5 g (yield 78%) of the product.
[0195] Meanwhile, FD-MS values of compounds P1-1 to P7-4 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.
TABLE-US-00003 compound FD-MS compound FD-MS P1-1 m/z=693.30(C.sub.52H.sub.39NO=693.89) P1-2 m/z=741.30(C.sub.56H.sub.39NO=741.93) P1-3 m/z=739.29(C.sub.56H.sub.37NO=739.92) P1-4 m/z=693.30(C.sub.52H.sub.39NO=693.89) P1-5 m/z=693.30(C.sub.52H.sub.39NO=693.89) P1-6 m/z=693.30(C.sub.52H.sub.39NO=693.89) P1-7 m/z=759.29(C.sub.56H.sub.38FNO=759.92) P1-8 m/z=817.33(C.sub.62H.sub.43NO=818.03) P1-9 m/z=766.30(C.sub.57H.sub.38N.sub.2O=766.94) P1-10 m/z=744.32(C.sub.56H.sub.32D.sub.5NO= 744.95) P1-11 m/z=816.31 (C.sub.61H.sub.40N.sub.2O=817.00) P1-12 m/z=816.31 (C.sub.61H.sub.40N.sub.2O=817.00) P1-13 m/z=693.30(C.sub.52H.sub.39NO=693.89) P1-14 m/z=769.33(C.sub.58H.sub.43NO=769.99) P1-15 m/z=711.29(C.sub.52H.sub.38FNO=711.88) P1-16 m/z=841.39(C.sub.62H.sub.51NO.sub.2=842.10) P1-17 m/z=709.28(C.sub.52H.sub.39NS=709.95) P1-18 m/z=757.28(C.sub.56H.sub.39NS=758.00) P1-19 m/z=831.30(C.sub.62H.sub.41 NS=832.08) P1-20 m/z=709.28(C.sub.52H.sub.39NS=709.95) P1-21 m/z=638.28(C.sub.46H.sub.30D.sub.5NS=638.88) P1-22 m/z=775.27(C.sub.56H.sub.38FNS=775.99) P1-23 m/z=755.26(C.sub.56H.sub.37NS=755.98) P1-24 m/z=805.28(C.sub.60H.sub.39NS=806.04) P1-25 m/z=709.28(C.sub.52H.sub.39NS=709.95) P1-26 m/z=727.27(C.sub.52H.sub.38FNS=727.94) P1-27 m/z=709.28(C.sub.52H.sub.39NS=709.95) P1-28 m/z=785.31(C.sub.58H.sub.43NS=786.05) P1-29 m/z=693.30(C.sub.52H.sub.39NO=693.89) P1-30 m/z=829.37(C.sub.61H.sub.51NS=830.15) P1-31 m/z=717.30(C.sub.54H.sub.39NO=717.91) P1-32 m/z=805.28(C.sub.60H.sub.39NS=806.04) P1-33 m/z=631.29(C.sub.47H.sub.37NO=631.82) P1-34 m/z=695.26(C.sub.51H.sub.37NS=695.92) P2-1 m/z=693.30(C.sub.52H.sub.39NO=693.89) P2-2 m/z=741.30(C.sub.56H.sub.39NO=741.93) P2-3 m/z=815.32(C.sub.62H.sub.41 NO=816.2) P2-4 m/z=693.30(C.sub.52H.sub.39NO=693.89) P2-5 m/z=635.26(C.sub.46H.sub.34FNO=635.78) P2-6 m/z=667.29(C.sub.50H.sub.37NO=667.85) P2-7 m/z=817.33(C.sub.62H.sub.43NO=818.03) P2-8 m/z=741.30(C.sub.56H.sub.39NO=741.93) P2-9 m/z=766.30(C.sub.57H.sub.38N.sub.2O=766.94) P2-10 m/z=789.30(C.sub.60H.sub.39NO=789.98) P2-11 m/z=815.32(C.sub.62H.sub.41 NO=816.02) P2-12 m/z=831.31(C.sub.62H.sub.41NO.sub.2=832.02) P2-13 m/z=698.33(C.sub.52H.sub.34D.sub.5NO=698.92) P2-14 m/z=769.33(C.sub.58H.sub.43NO=769.99) P2-15 m/z=743.32(C.sub.56H.sub.41 NO=743.95) P2-16 m/z=769.33(C.sub.58H.sub.43NO=769.99) P2-17 m/z=633.25(C.sub.46H.sub.35NS=633.85) P2-18 m/z=833.31 (C.sub.62H.sub.43NS=834.09) P2-19 m/z=805.28(C.sub.60H.sub.39NS=806.04) P2-20 m/z=709.28(C.sub.52H.sub.39NS=709.95) P2-21 m/z=683.26(C.sub.50H.sub.37NS=683.91) P2-22 m/z=833.31 (C.sub.62H.sub.43NS=834.09) P2-23 m/z=823.27 (C.sub.60H.sub.38FNS=824.03) P2-24 m/z=780.26(C.sub.57H.sub.36N.sub.2S=780.99) P2-25 m/z=709.28(C.sub.52H.sub.39NS=709.95) P2-26 m/z=709.28(C.sub.52H.sub.39NS=709.95) P2-27 m/z=709.28(C.sub.52H.sub.39NS=709.95) P2-28 m/z=785.31 (C.sub.58H.sub.43NS=786.05) P2-29 m/z=753.30(C.sub.57H.sub.39NO=753.95) P2-30 m/z=647.88(C.sub.47H.sub.37NS=647.88) P3-1 m/z=693.30(C.sub.52H.sub.39NO=693.89) P3-2 m/z=791.32(C.sub.60H.sub.41 NO=791.99) P3-3 m/z=815.32(C.sub.62H.sub.41 NO=816.02) P3-4 m/z=617.27(C.sub.46H.sub.35NO=617.79) P3-5 m/z=667.29(C.sub.50H.sub.37NO=667.85) P3-6 m/z=667.29(C.sub.50H.sub.37NO=667.85) P3-7 m/z=759.29(C.sub.56H.sub.38FNO=759.92) P3-8 m/z=817.33(C.sub.62H.sub.43NO=818.03) P3-9 m/z=741.30(C.sub.56H.sub.39NO=741.93) P3-10 m/z=744.32(C.sub.56H.sub.32D.sub.5NO= 744.95) P3-11 m/z=789.30(C.sub.60H.sub.39NO=789.98) P3-12 m/z=739.29(C.sub.56H.sub.37NO=739.92) P3-13 m/z=693.30(C.sub.52H.sub.39NO=693.89) P3-14 m/z=793.33(C.sub.60H.sub.43NO=794.01) P3-15 m/z=743.32(C.sub.56H.sub.41 NO=743.95) P3-16 m/z=769.33(C.sub.58H.sub.43NO=769.99) P3-17 m/z=709.28(C.sub.52H.sub.39NS=709.95) P3-18 m/z=833.31 (C.sub.62H.sub.43NS=834.09) P3-19 m/z=831.30(C.sub.62H.sub.41 NS=832.08) P3-20 m/z=651.24(C.sub.46H.sub.34FNS=651.84) P3-21 m/z=633.25(C.sub.46H.sub.35NS=633.85) P3-22 m/z=757.28(C.sub.56H.sub.39NS=758.00) P3-23 m/z=832.29(C.sub.61 H.sub.40N.sub.2S=833.07) P3-24 m/z=831.30(C.sub.62H.sub.41NS=832.08) P3-25 m/z=709.28(C.sub.52H.sub.39NS=709.95) P3-26 m/z=709.28(C.sub.52H.sub.39NS=709.95) P3-27 m/z=759.30(C.sub.56H.sub.41 NS=760.01) P3-28 m/z=835.33(C.sub.62H.sub.45NS=836.11) P3-29 m/z=647.26(C.sub.47H.sub.37NS=647.88) P3-30 m/z=631.29(C.sub.47H.sub.37NO=631.82) P4-1 m/z=723.26(C.sub.52H.sub.37NOS=723.93) P4-2 m/z=707.28(C.sub.52H.sub.37NO.sub.2=707.87) P4-3 m/z=857.37(C.sub.65H.sub.47NO=858.10) P4-4 m/z=829.30(C.sub.62H.sub.39NO.sub.2=830.00) P4-5 m/z=782.33(C.sub.58H.sub.42N.sub.2O=782.99) P4-6 m/z=855.35(C.sub.65H.sub.45NO=856.08) P4-7 m/z=881.33(C.sub.66H.sub.43NO.sub.2=882.08) P4-8 m/z=913.28(C.sub.66H.sub.40FNOS= 914.11) P4-9 m/z=739.24(C.sub.52H.sub.37NS.sub.2=740.00) P4-10 m/z=798.31 (C.sub.58H.sub.42N.sub.2S=799.05) P4-11 m/z=851.32(C.sub.62H.sub.37D.sub.4NOS= 852.10) P4-12 m/z=861.25(C.sub.62H.sub.39NS.sub.2=862.12) P4-13 m/z=749.31 (C.sub.55H.sub.43NS=750.02) P4-14 m/z=848.32(C.sub.62H.sub.44N.sub.2S=849.11) P4-15 m/z=940.29(C.sub.67H.sub.44N.sub.2S.sub.2=941.22) P4-16 m/z=921.31 (C.sub.68H.sub.43NOS=922.16) P4-17 m/z=997.34(C.sub.74H.sub.47NOS=998.26) P4-18 m/z=923.32(C.sub.68H.sub.45NOS=924.17) P4-19 m/z=982.39(C.sub.74H.sub.50N.sub.2O=983.23 P4-20 m/z=885.40(C.sub.67H.sub.51NO=886.15) P5-1 m/z=707.28(C.sub.52H.sub.37NO.sub.2=707.87) P5-2 m/z=723.26(C.sub.52H.sub.37NOS= 723.93) P5-3 m/z=782.33(C.sub.58H.sub.42N.sub.2O=782.99) P5-4 m/z=733.33(C.sub.55H.sub.43NO=733.96) P5-5 m/z=707.28(C.sub.52H.sub.37NO.sub.2=707.87) P5-6 m/z=707.28(C.sub.52H.sub.37NO.sub.2=707.87) P5-7 m/z=707.28(C.sub.52H.sub.37NO.sub.2=707.87) P5-8 m/z=723.26(C.sub.52H.sub.37NOS= 723.93) P5-9 m/z=723.26(C.sub.52H.sub.37NOS=723.93) P5-10 m/z=782.33(C.sub.58H.sub.42N.sub.2O=782.99) P5-11 m/z=782.33(C.sub.58H.sub.42N.sub.2O=782.99) P5-12 m/z=733.33(C.sub.55H.sub.43NO=733.96) P5-13 m/z=733.33(C.sub.55H.sub.43NO=733.96) P5-14 m/z=857.37(C.sub.65H.sub.47NO=858.10) P5-15 m/z=855.35(C.sub.65H.sub.45NO=856.08) P5-16 m/z=831.31(C.sub.62H.sub.41NO.sub.2=832.02) P5-17 m/z=829.30(C.sub.62H.sub.39NO.sub.2=830.00) P5-18 m/z=723.26(C.sub.52H.sub.37NOS= 723.93) P5-19 m/z=733.33(C.sub.55H.sub.43NO=733.96) P5-20 m/z=782.33(C.sub.58H.sub.42N.sub.2O=782.99) P5-21 m/z=831.31 (C.sub.62H.sub.41NO.sub.2=832.02) P5-22 m/z=906.36(C.sub.68H.sub.46N.sub.2O=907.13) P5-23 m/z=881.33(C.sub.66H.sub.43NO.sub.2=882.08) P5-24 m/z=855.35(C.sub.65H.sub.45NO=856.08) P5-25 m/z=723.26(C.sub.52H.sub.37NOS=723.93) P5-26 m/z=848.32(C.sub.62H.sub.44N.sub.2S=849.11) P5-27 m/z=939.30(C.sub.68H.sub.45NS.sub.2=940.24) P5-28 m/z=845.28(C.sub.62H.sub.39NOS= 846.06) P5-29 m/z=799.29(C.sub.58H.sub.41 NOS=800.03) P5-30 m/z=825.34(C.sub.61H.sub.47NS=826.11) P5-31 m/z=913.28(C.sub.66H.sub.43NS.sub.2=914.20) P5-32 m/z=921.34(C.sub.69H.sub.47NS=922.20) P5-33 m/z=923.32(C.sub.68H.sub.42FNO.sub.2=924.09) P5-34 m/z=1025.41 (C.sub.77H.sub.55NS= 1026.35) P5-35 m/z=967.33(C.sub.70H.sub.49NS.sub.2=968.29) P5-36 m/z=885.40(C.sub.67H.sub.51NO=886.15) P5-37 m/z=763.33(C.sub.56H.sub.45NS=764.04) P5-38 m/z=819.31 (C.sub.61H.sub.41NO.sub.2=820.00) P6-1 m/z=723.26(C.sub.52H.sub.37NOS=723.93) P6-2 m/z=707.28(C.sub.52H.sub.37NO.sub.2=707.87) P6-3 m/z=847.29(C.sub.62H.sub.41NOS=848.08) P6-4 m/z=879.31 (C.sub.66H.sub.41NO.sub.2=880.06) P6-5 m/z=832.35(C.sub.62H.sub.44N.sub.2O=833.05) P6-6 m/z=733.33(C.sub.55H.sub.43NO=733.96) P6-7 m/z=981.40(C.sub.75H.sub.51NO=982.24) P6-8 m/z=829.30(C.sub.62H.sub.39NO.sub.2=830.00) P6-9 m/z=799.29(C.sub.58H.sub.41NOS=800.03) P6-10 m/z=848.32(C.sub.62H.sub.44N.sub.2S=849.11) P6-11 m/z=881.26(C.sub.62H.sub.40FNS.sub.2=882.13) P6-12 m/z=861.25(C.sub.62H.sub.39NS.sub.2=862.12) P6-13 m/z=871.33(C.sub.65H.sub.45NS=872.14) P6-14 m/z=799.29(C.sub.58H.sub.41NOS=800.03) P6-15 m/z=863.27(C.sub.62H.sub.41NS.sub.2=864.14) P6-16 m/z=871.33(C.sub.65H.sub.45NS=872.14) P6-17 m/z=1122.4(C.sub.84H.sub.54N.sub.2S=1123.43) P6-18 m/z=875.32(C.sub.64H.sub.45NOS= 876.13) P6-19 m/z=1085.46(C.sub.83H.sub.59NO=1086.39) P6-20 m/z=875.32(C.sub.64H.sub.45NOS= 876.13) P6-21 m/z=721.30(C.sub.53H.sub.39NO.sub.2=721.90) P6-22 m/z=753.25(C.sub.53H.sub.39NS.sub.2=754.02) P7-1 m/z=1148.47(C.sub.87H.sub.60N.sub.2O= 1149.45) P7-2 m/z=1162.43(C.sub.87H.sub.58N.sub.2S= 1163.50) P7-3 m/z=1330.49(C.sub.99H.sub.66N.sub.2OS= 1331.69) P7-4 m/z=1148.47(C.sub.87H.sub.60N.sub.2O= 1149.45)
Evaluation of Manufacture of Organic Electronic Element
[Example 1] Green Organic Light Emitting Diode (Hole Transport Layer)
[0196] An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a hole transport layer material.
[0197] First, on an ITO layer (anode) formed on a glass substrate, N1-(naphthalen-2-yl)-N4, N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N 1-phenylbenzene-1,4-diamine (Hereinafter, abbreviated as 2-TNATA) film as a hole injection layer was vacuum-deposited to form a thickness of 60 nm. On the hole injection layer, the compound P1-1 of the present invention was vacuum-deposited to a thickness of 60 nm to form a hole transport layer. After forming the hole transport layer, CBP[4,4′-N,N′-dicarbazole-biphenyl] was used as a host, and lr(ppy).sub.3 [tris(2-phenylpyridine)-iridium] was used as a dopant, doped at a weight ratio of 95:5, and vacuum deposited to a thickness of 30 nm to form an emitting layer on hole transport layer. Then (1,1′-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (hereinafter abbreviated as BAlq) as a hole blocking layer was vacuum-deposited to a thickness of 10 nm, as an electron transport layer, tris(8-quinolinol)aluminum (hereinafter, abbreviated as Alq3) was deposited to a thickness of 40 nm. Thereafter, LiF, which is an alkali metal halide, was deposited as an electron injection layer to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm and used as a cathode to prepare an organic electroluminescent device.
[Example 2] to [Example 51] Green Organic Light Emitting Diode (Hole Transport Layer)
[0198] An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound P1-2 to P7-3 of the present invention described in Table 4 was used instead of the compound P1-1 of the present invention as a hole transport layer material.
[Comparative Example 1] or [Comparative Example 2]
[0199] An organic electroluminescent device was manufactured in the same manner as in Example 1, except for using Comparative Compound A or Comparative Compound B instead of Compound P1-1 of the present invention as the hole transport layer material
##STR00507##
##STR00508##
By applying a forward bias DC voltage to the organic electroluminescent devices prepared in Examples and Comparative Examples prepared in this way, Electroluminescence (EL) characteristics were measured with PR-650 from Photoresearch, and as a result of the measurement, the T95 lifetime was measured using a lifetime measuring device manufactured by McScience at 5000 cd/m.sup.2 standard luminance. Table 4 below shows the device fabrication and evaluation results.
TABLE-US-00004 compound Voltage Current Density (mA/cm .sup.2) Brightn ess (cd/m.sup.2) Efficie ncy (cd/A) T(95) CIE X y comparative example(1) comparativ e compound 5.3 17.6 5000 28.4 84.6 0.35 0.61 A comparative example(2) comparativ e compound B 5.5 18.2 5000 27.4 88.9 0.35 0.63 example(1) compound (P1-1) 4.7 13.3 5000 37.6 107.0 0.34 0.61 example(2) compound (P1-4) 4.7 13.7 5000 36.6 105.0 0.32 0.64 example(3) compound (P1-5) 4.9 15.0 5000 33.2 99.2 0.33 0.60 example(4) compound (P1-13) 4.7 13.6 5000 36.8 104.9 0.31 0.65 example(5) compound (P1-14) 4.8 14.2 5000 35.2 107.2 0.31 0.61 example(6) compound (P1-17) 4.8 14.1 5000 35.5 102.0 0.34 0.62 example(7) compound (P1-18) 4.9 14.4 5000 34.8 104.0 0.31 0.64 example(8) compound (P1-24) 5.2 16.6 5000 30.1 96.2 0.32 0.65 example(9) compound (P1-33) 4.6 13.9 5000 36.1 111.3 0.32 0.63 example(10) compound (P2-1 ) 4.6 12.8 5000 39.1 111.2 0.34 0.64 example(11) compound (P2-2) 4.7 13.1 5000 38.3 113.8 0.34 0.61 example(12) compound (P2-3) 4.6 13.3 5000 37.7 115.7 0.34 0.61 example(13) compound (P2-7) 4.9 14.4 5000 34.7 105.2 0.31 0.63 example(14) compound (P2-8) 4.9 14.3 5000 34.9 106.3 0.31 0.63 example(15) compound (P2-11 4.8 14.6 5000 34.2 108.3 0.31 0.62 example(16) compound (P2-17) 4.7 13.2 5000 37.9 108.2 0.34 0.65 example(17) compound (P2-18) 4.8 13.4 5000 37.2 110.4 0.32 0.64 example(18) compound (P2-20) 4.7 13.5 5000 36.9 106.0 0.34 0.62 example(19) compound (P2-21) 4.9 15.1 5000 33.1 98.2 0.31 0.62 example(20) compound (P2-22) 5.0 14.7 5000 33.9 103.2 0.31 0.60 example(21) compound (P2-29) 4.5 13.8 5000 36.3 120.3 0.31 0.64 example(22) compound (P3-1) 4.7 12.6 5000 39.8 113.4 0.35 0.63 example(23) compound (P3-3) 4.7 13.1 5000 38.2 117.9 0.34 0.62 example(24) compound (P3-4) 4.7 12.9 5000 38.8 111.3 0.30 0.63 example(25) compound (P3-12) 5.0 14.5 5000 34.5 107.2 0.34 0.61 example(26) compound (P3-17) 4.7 13.0 5000 38.6 110.1 0.32 0.61 example(27) compound (P3-25) 4.8 13.2 5000 38.0 108.0 0.32 0.61 example(28) compound (P3-26) 4.9 14.0 5000 35.6 103.9 0.34 0.64 example(29) compound (P3-29) 4.7 13.7 5000 36.4 112.2 0.32 0.61 example(30) compound (P4-2) 4.6 13.2 5000 37.8 108.6 0.30 0.63 example(31) compound (P4-11) 4.7 13.4 5000 37.4 111.0 0.32 0.60 example(32) compound (P4-13) 4.7 13.8 5000 36.2 101.0 0.31 0.61 example(33) compound (P5-1) 4.5 12.6 5000 39.6 113.0 0.34 0.62 example(34) compound (P5-2) 4.6 12.9 5000 38.7 110.8 0.32 0.60 example(35) compound (P5-3) 4.6 12.7 5000 39.3 111.5 0.30 0.60 example(36) compound (P5-4) 4.5 12.5 5000 39.9 110.2 0.33 0.62 example(37) compound (P5-5) 4.5 12.7 5000 39.5 112.9 0.32 0.64 example(38) compound (P5-6) 4.5 12.5 5000 40.1 113.5 0.31 0.65 example(39) compound (P5-7) 4.5 12.7 5000 39.4 112.3 0.35 0.61 example(40) compound (P5-8) 4.6 13.0 5000 38.5 110.7 0.31 0.61 example(41) compound (P5-16) 4.6 12.9 5000 38.9 115.2 0.31 0.62 example(42) compound (P5-17) 4.6 13.1 5000 38.1 117.4 0.31 0.63 example(43) compound (P5-25) 4.6 13.0 5000 38.4 109.6 0.35 0.64 example(44) compound (P5-28) 4.7 13.6 5000 36.8 114.0 0.33 0.64 example(45) compound (P5-31) 5.1 15.8 5000 31.7 100.6 0.32 0.60 example(46) compound (P5-38) 4.8 15.5 5000 32.3 109.9 0.33 0.60 example(47) compound (P6-1) 4.7 12.7 5000 39.2 112.8 0.33 0.62 example(48) compound (P6-12) 4.8 13.5 5000 37.0 113.9 0.34 0.64 example(49) compound (P6-16) 4.9 14.5 5000 34.6 106.2 0.30 0.64 example(50) compound (P6-21) 4.6 13.5 5000 37.1 122.0 0.31 0.64 example(51) compound (P7-3) 4.7 15.2 5000 32.8 97.7 0.30 0.62
[0200] As can be seen from the results in Table 4, when a green organic electric device is manufactured using the material for an organic electric device of the present invention as a hole transport layer material, the performance of the organic electroluminescent device can be improved compared to the comparative example using the comparative compound A or the comparative compound B.
[0201] In other words, if Comparative Example 1 using Comparative Compound A is compared with Comparative Example 2 using Comparative Compound B, the results of Comparative Example 1 showed excellent results in terms of driving voltage, and Comparative Example 2 showed excellent results in terms of efficiency and lifespan. Also, Examples 1 to 51 of the compound of the present invention showed remarkably excellent results in efficiency and lifetime.
[Example 52] Green Organic Light Emitting Diode (Emitting Auxiliary Layer)
[0202] An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as an emitting auxiliary layer material.
[0203] First, on an ITO layer (anode) formed on a glass substrate, N1-(naphthalen-2-yl)-N4, N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N 1-phenylbenzene-1,4-diamine (Hereinafter, abbreviated as 2-TNATA) film as a hole injection layer was vacuum-deposited to form a thickness of 60 nm. 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPB) was vacuum-deposited on the hole injection layer to a thickness of 60 nm to form a hole transport layer. Then, as a material for the emitting auxiliary layer, the compound P1-1 of the present invention was vacuum-deposited to a thickness of 20 nm to form an emitting auxiliary layer. After forming the emitting auxiliary layer, CBP[4,4′-N,N′-dicarbazole-biphenyl] was used as a host, and lr(ppy).sub.3 [tris(2-phenylpyridine)-iridium] was used as a dopant, doped at a weight ratio of 95:5, and vacuum deposited to a thickness of 30 nm to form an emitting layer on the emitting auxiliary layer. (1,1′-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (hereinafter abbreviated as BAlq) as a hole blocking layer was vacuum-deposited to a thickness of 10 nm, as an electron transport layer, tris(8-quinolinol)aluminum (hereinafter, abbreviated as Alq3) was deposited to a thickness of 40 nm. Thereafter, LiF, which is an alkali metal halide, was deposited as an electron injection layer to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm and used as a cathode to prepare an organic electroluminescent device.
[Example 53] to [Example 102] Green Organic Light Emitting Diode (Emitting Auxiliary Layer)
[0204] An organic electroluminescent device was manufactured in the same manner as in Example 47, except that the compound P1-2 to P7-3 of the present invention described in Table 5 was used instead of the compound P1-1 of the present invention as an emitting auxiliary layer material.
[Comparative Example 3]
[0205] An organic electroluminescent device was manufactured in the same manner as in Example 47, except that the emitting auxiliary layer was not used.
[Comparative Example 4] or [Comparative Example 5]
[0206] An organic electroluminescent device was manufactured in the same manner as in Example 47, Except for using Comparative Compound A or Comparative Compound B instead of Compound P1-1 of the present invention as the emitting auxiliary layer material
[0207] By applying a forward bias DC voltage to the organic electroluminescent devices prepared in Examples and Comparative Examples prepared in this way, Electroluminescence (EL) characteristics were measured with PR-650 from Photoresearch, and as a result of the measurement, the T95 lifetime was measured using a lifetime measuring device manufactured by McScience at 5000 cd/m.sup.2 standard luminance. Table 4 below shows the device fabrication and evaluation results.
TABLE-US-00005 compound Voltage Current Density (mA/cm 2) Bright ness (cd/m.sup.2 ) Effici ency (cd/A ) T(95) CIE X y comparative example(1) 6.7 68.5 5000 7.3 62.9 0.31 0.63 comparative example(2) comparativ e compound A 5.4 14.4 5000 34.6 97.9 0.30 0.63 comparative example(3) comparativ e compound B 5.6 15.0 5000 33.4 102.9 0.30 0.61 example(52) compound (P1-1) 4.9 10.9 5000 45.8 123.8 0.31 0.64 example(53) compound (P1-4) 5.0 11.2 5000 44.6 121.5 0.31 0.63 example(54) compound (P1-5) 5.2 12.3 5000 40.5 114.8 0.32 0.63 example(55) compound (P1-13) 5.0 11.2 5000 44.8 121.4 0.31 0.64 example(56) compound (P1-14) 5.1 11.7 5000 42.9 123.9 0.31 0.62 example(57) compound (P1-17) 5.1 11.5 5000 43.3 118.0 0.33 0.65 example(58) compound (P1-18) 5.2 11.8 5000 42.5 120.4 0.31 0.61 example(59) compound (P1-24) 5.4 13.6 5000 36.7 111.4 0.32 0.64 example(60) compound (P1-33) 4.8 11.4 5000 44.0 128.8 0.35 0.61 example(61) compound (P2-1) 4.8 10.5 5000 47.6 128.7 0.31 0.61 example(62) compound (P2-2) 5.0 10.7 5000 46.8 131.4 0.32 0.61 example(63) compound (P2-3) 4.9 10.9 5000 45.9 133.9 0.35 0.63 example(64) compound (P2-7) 5.2 11.8 5000 42.3 121.8 0.31 0.62 example(65) compound (P2-8) 5.2 11.7 5000 42.6 123.0 0.30 0.63 example(66) compound (P2-11 5.1 12.0 5000 41.8 125.4 0.32 0.61 example(67) compound (P2-17) 4.9 10.8 5000 46.2 125.0 0.32 0.63 example(68) compound (P2-18) 5.1 11.0 5000 45.4 127.7 0.35 0.64 example(69) compound (P2-20) 5.0 11.1 5000 45.0 122.7 0.34 0.63 example(70) compound (P2-21) 5.2 12.5 5000 40.1 113.6 0.30 0.63 example(71) compound (P2-22) 5.3 12.1 5000 41.3 119.4 0.34 0.61 example(72) compound (P2-29) 4.8 11.4 5000 43.9 139.3 0.33 0.64 example(73) compound (P3-1 ) 4.9 10.3 5000 48.6 131.2 0.31 0.61 example(74) compound (P3-3) 5.0 10.7 5000 46.7 136.5 0.32 0.64 example(75) compound (P3-4) 5.0 10.6 5000 47.3 128.8 0.31 0.61 example(76) compound (P3-12) 5.3 11.9 5000 42.1 124.1 0.34 0.64 example(77) compound (P3-17) 5.0 10.6 5000 47.1 127.4 0.32 0.62 example(78) compound (P3-25) 5.1 10.8 5000 46.3 124.9 0.31 0.63 example(79) compound (P3-26) 5.2 11.5 5000 43.4 120.3 0.34 0.62 example(80) compound (P3-29) 5.0 11.3 5000 44.4 129.9 0.32 0.65 example(81) compound (P4-2) 4.9 10.8 5000 46.1 125.6 0.32 0.61 example(82) compound (P4-11) 5.0 11.0 5000 45.6 128.3 0.33 0.64 example(83) compound (P4-13) 5.0 11.3 5000 44.2 116.8 0.34 0.61 example(84) compound (P5-1) 4.7 10.3 5000 48.4 130.8 0.30 0.61 example(85) compound (P5-2) 4.8 10.5 5000 47.4 128.2 0.34 0.63 example(86) compound (P5-3) 4.8 10.5 5000 47.7 129.0 0.30 0.63 example(87) compound (P5-4) 4.7 10.3 5000 48.7 127.5 0.35 0.62 example(88) compound (P5-5) 4.8 10.4 5000 48.1 130.7 0.31 0.62 example(89) compound (P5-6) 4.8 10.2 5000 48.9 131.3 0.33 0.61 example(90) compound (P5-7) 4.8 10.4 5000 47.9 130.0 0.35 0.63 example(91) compound (P5-8) 4.8 10.6 5000 47.2 128.1 0.35 0.64 example(92) compound (P5-16) 4.9 10.5 5000 47.5 133.3 0.34 0.61 example(93) compound (P5-17) 4.8 10.8 5000 46.5 135.9 0.31 0.62 example(94) compound (P5-25) 4.8 10.7 5000 46.9 126.9 0.32 0.63 example(95) compound (P5-28) 4.9 11.1 5000 44.9 131.9 0.33 0.62 example(96) compound (P5-31) 5.3 12.9 5000 38.9 116.4 0.35 0.62 example(97) compound (P5-38) 5.0 12.7 5000 39.4 127.2 0.35 0.64 example(98) compound (P6-1) 4.9 10.4 5000 48.2 130.6 0.35 0.61 example(99) compound (P6-12) 5.1 11.1 5000 45.1 132.1 0.31 0.64 example(100) compound (P6-16) 5.2 11.8 5000 42.2 122.9 0.32 0.60 example(101) compound (P6-21) 4.9 11.0 5000 45.3 141.2 0.32 0.62 example(102) compound (P7-3) 5.0 12.4 5000 40.2 113.1 0.34 0.60
[0208] As can be seen from the results in Table 5, when a green organic electric device is manufactured using the material for an organic electric device of the present invention as an emitting auxiliary layer material, the efficiency and lifespan of the organic electroluminescent device can be improved compared to the comparative example in which the emitting auxiliary layer is not used or the comparative compound A or the comparative compound B is used.
[0209] In other words, the results of Comparative Example 4 or Comparative Example 5 using Comparative Compound A or Comparative Compound B were superior to Comparative Example 3 without using the emitting auxiliary layer, and Examples 52 to 102 of the compound of the present invention showed remarkably excellent results in terms of efficiency and lifespan.
[0210] First, if the comparative compound A and the compound of the present invention are compared, there is a difference between the comparative compound A and the compound of the present invention in that the bonding position of the amino group to the fluorene is different. When fluorene is bonded to an amino group, the energy level (especially HOMO and LUMO) is changed depending on the bonding position, and the physical properties of the compound are changed. Accordingly, as the physical properties of the compound are changed, the charge balance in the emitting layer is increased, and light emission is performed well inside the emitting layer rather than the interface of the emitting layer. As a result, degradation at the interface of the emitting layer is also reduced, and efficiency and lifespan are improved. Therefore, it is determined that this point acts as a major factor in improving device performance during device deposition.
[0211] Second, comparing the comparative compound B and the compound of the present invention, Comparative Compound B has a structure in which a dibenzofuran structure is bonded to an amino group, and the compound of the present invention has a structure in which xanthene and thioxanthene structures are bonded to an amino group. In other words, when comparing dibenzofuran and xanthene, the xanthene structure is judged to have improved electron donating ability and improved hole properties as sp3 carbon is added. As the xanthene structure was introduced, the hole characteristics were improved and the driving voltage, efficiency, and lifespan were improved.
[0212] As a result, when the diphenylfluorene and xanthene structures are simultaneously substituted with amino groups as in the compound of the present invention, it is judged that the device performance is remarkably excellent due to the synergy between diphenylfluorene and xanthene.
[0213] Although exemplary embodiments of the present invention have been described for illustrative purposes, those skilled in the art will appreciate that various modifications, additions and substitutions are possible, without departing from the scope and spirit of the invention as disclosed in the accompanying claims. Therefore, the embodiment disclosed in the present invention is intended to illustrate the scope of the technical idea of the present invention, and the scope of the present invention is not limited by the embodiment. The scope of the present invention shall be construed on the basis of the accompanying claims, and it shall be construed that all of the technical ideas included within the scope equivalent to the claims belong to the present invention.
Industrial Applicability
[0214] According to the present invention, it is possible to manufacture an organic device having excellent device characteristics of high luminance, high light emission and long lifespan, and thus there is industrial applicability.