COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF

Abstract

Provided are a compound capable of improving the luminous efficiency, stability and lifespan of a device employing the same, an organic electronic element employing the same, and an electronic device thereof.

Claims

1. A compound represented by Formula 1-1: ##STR00071## wherein: 1) L.sup.1 is a substituent represented by any one of Formulas L-1 to L-4: ##STR00072## 2) L.sup.2 is a single bond or a C.sub.6˜C.sub.60 arylene group, 3) Ar is a C.sub.6˜C.sub.60 aryl group, 4) Ring A is a substituent represented by Formula a, or Formula b: ##STR00073##

5. R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are the same or different from each other and are each independently hydrogen or deuterium,

6. R.sup.7 is selected from the group consisting of hydrogen; deuterium; a C.sub.6˜C.sub.60 aryl group; and a C.sub.6˜C.sub.60 aryl group substituted with deuterium,

7. a and d are each an integer of 0 to 5; b and f are each an integer of 0 to 6; c, e, g and h are each an integer of 0 to 4; and i is an integer of 0 to 7,

8. * refers to the position to be bonded,

9. wherein the aryl group and the arylene group may be further substituted with one or more substituents selected from the group consisting of deuterium; a C.sub.6˜C.sub.20 aryl group; and a C.sub.6˜C.sub.20 aryl group substituted with deuterium.

2. The compound of claim 1, wherein Formula 1-1 is represented by Formula 1-1-a or Formula 1-1-b: ##STR00074## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.7, L.sup.1, L.sup.2, Ar, a, b, c, d and i are the same as defined in claim

1.

3. The compound of claim 1, wherein Formula 1-1 is represented by any one of Formulas 1-1-1 to 1-1-5: ##STR00075## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, L.sup.2, Ar, a, b, c, d, e, f, g, h and i are the same as defined in claim 1.

4. The compound of claim 1, wherein Formula 1-1 is represented by any one of Formulas 1-1-1-a to 1-1-1-c: ##STR00076## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, L.sup.2, Ar, a, b, c, d and e are the same as defined in claim 1.

5. The compound of claim 1, wherein Formula 1-1 is represented by any one of Formulas 1-1-2-a to 1-1-2-c: ##STR00077## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, L.sup.2, Ar, a, b, c, d and f are same as defined in claim 1.

6. The compound of claim 1, wherein Formula 1-1 is represented by Formula 1-1-3-a or Formula 1-1-3-b: ##STR00078## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, L.sup.2, Ar, a, b, c, d and f are the same as defined in claim 1.

7. The compound of claim 1, wherein Formula 1-1 is represented by Formula 1-1-4-a: ##STR00079## wherin R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, L.sup.2, Ar, a, b, c, d, g, and h are the same as defined in claim 1.

8. The compound of claim 1, wherein Formula 1-1 is represented by Formula 1-1-4-b or Formula 1-1-4-c: ##STR00080## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, L.sup.2, Ar, a, b, c, d, g and h are as the same as defined in claim 1.

9. The compound of claim 1, wherein Formula 1-1 is represented by any one of Formulas 1-1-5-a to 1-1-5-c: ##STR00081## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.5, R.sup.7, L.sup.2, Ar, a, b, c, e and i are the same as defined in claim 1.

10. The compound of claim 1, wherein the compound represented by Formula 1-1 is represented by any one of the following compounds P-1 to P-44: ##STR00082## ##STR00083## ##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088##

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 1-1 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 is an emitting layer.

14. The organic electronic element of claim 11, wherein the organic electronic device 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.

15. The organic electronic element of claim 11, wherein the organic material layer comprises 2 or more stacks including a hole transport layer, an emitting layer, and an electron transport layer sequentially formed on the anode.

16. The organic electronic element of claim 15, wherein the organic material layer further comprises a charge generation layer formed between the 2 or more stacks.

17. An electronic device comprising: a display device including the organic electronic element of claim 11; and a control unit for driving the display device.

18. The organic electronic element of claim 17, 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

[0014] FIG. 1 to FIG. 3 are each an exemplary view of an organic electroluminescent device according to the present invention.

[0015] The numbers used in each of the drawings refer to the following:

TABLE-US-00001 100, 200, 300: organic 110 : the first electrode electronic element 120 : hole injection layer 130 : hole transport layer 140 : emitting layer 150 : electron transport layer 160 : electron injection layer 170 : second electrode 180 : light efficiency enhancing Layer 210 : buffer layer 220 : emitting auxiliary layer 320 : first hole injection layer 330 : first hole transport layer 340 : first emitting layer 350 : first electron transport layer 360 : first charge generation layer 361 : second charge generation layer 420 : second hole injection layer 430 : second hole transport layer 440 : second emitting layer 450 : second electron transport layer CGL : charge generation layer ST1 : first stack ST2 : second stack

DETAILED DESCRIPTION

[0016] Hereinafter, some embodiments of the present invention will be described in detail. 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.

[0017] 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.

[0018] As used in the specification and the accompanying claims, unless otherwise stated, the following is the meaning of the term as follows.

[0019] Unless otherwise stated, the term “halo” or “halogen”, as used herein, includes fluorine, bromine, chlorine, or iodine.

[0020] 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.

[0021] 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.

[0022] 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.

[0023] 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.

[0024] 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.

[0025] 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.

[0026] For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

[0027] 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.

[0028] 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.

[0029] 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.

[0030] Unless otherwise stated, the term “heteroatom”, as used herein, represents at least one of N, O, S, P, or Si.

[0031] 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##

[0032] 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##

[0033] 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.

[0034] 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. 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.

[0035] Other hetero compounds or hetero radicals other than the above-mentioned hetero compounds include, but are not limited thereto, one or more heteroatoms.

[0036] 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.

[0037] 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##

[0038] Here, when a is an integer of 0, 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 combined 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##

[0039] Hereinafter, a compound according to an aspect of the present invention and an organic electronic element including the same will be described.

[0040] The present invention provides a compound represented by Formula 1-1.

##STR00006##

[0041] In Formula 1-1, each symbol may be defined as follows.

[0042] 1) L.sup.1 is a substituent represented by any one of Formulas L-1 to L-4,

##STR00007##

[0043] 2) L.sup.2 is a single bond; or a C.sub.6˜C.sub.60 arylene group;

[0044] 3) Ar is a C.sub.6˜C.sub.60 aryl group, preferably a C.sub.6˜C.sub.30 aryl group, more preferably a C.sub.6˜C.sub.24 aryl group, such as phenylene, biphenyl, naphthalene, terphenyl, etc.

[0045] 4) Ring A is a substituent represented by Formula a; or Formula b;

##STR00008##

[0046] 5) R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are the same or different from each other and are each independently hydrogen; or deuterium;

[0047] 6) R.sup.7 is selected from the group consisting of hydrogen; deuterium; a C.sub.6˜C.sub.60 aryl group; and a C.sub.6˜C.sub.60 aryl group substituted with deuterium;

[0048] 7) a and d are independently of each other an integer of 0 to 5, [0049] b and f are independently of each other an integer of 0 to 6, [0050] c, e, g and h are each independently an integer from 0 to 4, [0051] i is an integer from 0 to 7,

[0052] 8) * means the position to be bonded,

[0053] 9) Here, the aryl group and the arylene group may be further substituted with one or more substituents selected from the group consisting of deuterium; a C.sub.6˜C.sub.20 aryl group; and a C.sub.6˜C.sub.20 aryl group substituted with deuterium; respectively.

[0054] L.sup.2 may be represented by any one of Formulas a-1 to a-20.

##STR00009## ##STR00010## ##STR00011## ##STR00012##

[0055] In Formulas a-1 to a-20, each symbol may be defined as follows.

[0056] 1) R.sup.101 and R.sup.102 are each the same or different, and each independently hydrogen; deuterium; a C.sub.6˜C.sub.20 aryl group; or a C.sub.6˜C.sub.20 aryl group substituted with deuterium;

[0057] In case R.sup.101 and R.sup.102 are aryl groups, they may be phenylene, biphenyl, naphthalene, terphenyl, etc.;

[0058] 2) aa, ab and ac are each independently an integer from 0 to 4, ad is an integer from 0 to 6, ae is an integer from 0 to 8,

[0059] 3) * means a position at which triazine or Ar is bonded.

[0060] Ar may be represented by any one of Formulas b-1 to b-8.

##STR00013## ##STR00014##

[0061] In Formulas b-1 to b-8, each symbol may be defined as follows.

[0062] 1) R.sup.103 is hydrogen; deuterium; a C.sub.6˜C.sub.20 aryl group; or a C.sub.6˜C.sub.20 aryl group substituted with deuterium;

[0063] In case R.sup.103 is aryl group, it may be phenylene, biphenyl, naphthalene, terphenyl, etc.;

[0064] 2) ba is an integer from 0 to 5, bb is an integer from 0 to 7, be is an integer from 0 to 9,

[0065] 3) means a position to be bonded to L.

[0066] Formula L-1 may be preferably represented by any one of Formulas L-1-1 to L-1-3.

##STR00015##

{In Formulas L-1-1 to L-1-3, R.sup.5, e and * are as defined above.}

[0067] Formula L-2 may be preferably represented by any one of Formulas L-2-1 to L-2-4.

##STR00016##

{In Formulas L-2-1 to L-2-4, R.sup.5, f and * are as defined above.}

[0068] Formula L-3 may be preferably represented by any one of Formulas L-3-1 to L-3-8.

##STR00017## ##STR00018##

{In Formulas L-3-1 to L-3-8, R.sup.5, f and * are as defined above.}

[0069] Formula L-4 may preferably be represented by any one of Formulas L-4-1 to L-4-6.

##STR00019##

{In Formulas L-4-1 to L-4-6, R.sup.5, R.sup.6, g, h, and * are as defined above.}

[0070] Also, Formula 1-1 is represented by Formula 1-1-a or Formula 1-1-b.

##STR00020##

{In Formula 1-1-a or Formula 1-1-b, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.7, L.sup.1, L.sup.2, Ar, a, b, c, d and i are the same as defined above.}

[0071] Also, Formula 1-1 is represented by any one of Formulas 1-1-1 to 1-1-5.

##STR00021## ##STR00022##

{In Formulas 1-1-1 to 1-1-5, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, L.sup.2, Ar, a, b, c, d, e, f, g, h and i are the same as defined above.}

[0072] Also, Formula 1-1 is represented by any one of Formulas 1-1-1-a to 1-1-1-c.

##STR00023##

{In Formulas 1-1-1-a to 1-1-1-c, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, L.sup.2, Ar, a, b, c, d and e are the same as defined above.}

[0073] Also, Formula 1-1 is represented by any one of Formulas 1-1-2-a to 1-1-2-c

##STR00024##

{In Formulas 1-1-2-a to 1-1-2-c, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, L.sup.2, Ar, a, b, c, d and f are same as defined above.}

[0074] Also, Formula 1-1 is represented by Formula 1-1-3-a or Formula 1-1-3-b,

##STR00025##

{In Formula 1-1-3-a or Formula 1-1-3-b, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, L.sup.2, Ar, a, b, c, d and f are the same as defined above.}

[0075] Also, Formula 1-1 is represented by Formula 1-1-4-a.

##STR00026##

{In Formula 1-1-4-a, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, L.sup.2, Ar, a, b, c, d, g, and h are as defined above.}

[0076] Also, Formula 1-1 is represented by Formula 1-1-4-b or Formula 1-1-4-c.

##STR00027##

{In Formula 1-1-4-b or Formula 1-1-4-c, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, L.sup.2, Ar, a, b, c, d, g and h are as the same as defined above.}

[0077] Also, Formula 1-1 is represented by any one of Formulas 1-1-5-a to 1-1-5-c.

##STR00028##

{In Formulas 1-1-5-a to 1-1-5-c, R.sup.1, R.sup.2, R.sup.3, R.sup.5, R.sup.7, L.sup.2, Ar, a, b, c, e and i are the same as defined above.}

[0078] Also, the compound represented by Formula 1-1 is represented by any one of the following compounds P-1 to P-44

##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035##

[0079] Referring to FIG. 1, the organic electronic element (100) according to the present invention includes a first electrode (110), a second electrode (170), and an organic material layer including a single compound or 2 or more compounds represented by Formula 1 between the first electrode (110) and the second electrode (170). In this case, the first electrode (110) may be an anode, and the second electrode (170) may be a cathode. In the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

[0080] 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 FIG. 2)

[0081] 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 hole blocking layer or 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 an emitting layer.

[0082] The organic material layer may comprise 2 or more stacks comprising 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 FIG. 3).

[0083] 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. 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.

[0084] 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.

[0085] 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.

[0086] Also, the present invention provides a composition for an emitting layer comprising the compound represented by Formula (1), and provides an organic electronic element comprising the emitting layer.

[0087] 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;

[0088] 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.

[0089] 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

[0090] The compound (final product) represented by Formula 1-1 according to the present invention is synthesized as shown in Reaction Scheme 1, but is not limited thereto.

##STR00036##

I. Synthesis of Sub1

[0091] The compound belonging to Sub1 may be the following compounds, but is not limited thereto, and Table 1 below shows FD-MS (Field Desorption-Mass Spectrometry) values of the compounds belonging to Sub1.

##STR00037## ##STR00038## ##STR00039## ##STR00040## ##STR00041## ##STR00042## ##STR00043##

TABLE-US-00002 TABLE 1 compound FD-MS Sub1-1 m/z = 280.16 (C.sub.18H.sub.21BO.sub.2 = 280.17) Sub1-2 m/z = 280.16 (C.sub.18H.sub.21BO.sub.2 = 280.17 Sub1-3 m/z = 285.19 (C.sub.18H.sub.16D.sub.5BO.sub.2 = 285.2) Sub1-4 m/z = 280.16 (C.sub.18H.sub.21BO.sub.2 = 280.17) Sub1-5 m/z = 330.18 (C.sub.22H.sub.23BO.sub.2 = 330.23) Sub1-6 m/z = 330.18 (C.sub.22H.sub.23BO.sub.2 = 330.23) Sub1-7 m/z = 330.18 (C.sub.22H.sub.23BO.sub.2 = 330.23) Sub1-8 m/z = 330.18 (C.sub.22H.sub.23BO.sub.2 = 330.23) Sub1-9 m/z = 335.21 (C.sub.22H.sub.18D.sub.5BO.sub.2 = 335.26) Sub1-10 m/z = 330.18 (C.sub.22H.sub.23BO.sub.2 = 330.23) Sub1-11 m/z = 335.21 (C.sub.22H.sub.18D.sub.5BO.sub.2 = 335.26) Sub1-12 m/z = 356.19 (C.sub.24H.sub.25BO.sub.2 = 356.27) Sub1-13 m/z = 360.22 (C.sub.24H.sub.21D.sub.4BO.sub.2 = 360.3) Sub1-14 m/z = 356.19 (C.sub.24H.sub.25BO.sub.2 = 356.27) Sub1-15 m/z = 330.18 (C.sub.22H.sub.23BO.sub.2 = 330.23) Sub1-16 m/z = 330.18 (C.sub.22H.sub.23BO.sub.2 = 330.23) Sub1-17 m/z = 330.18 (C.sub.22H.sub.23BO.sub.2 = 330.23) Sub1-18 m/z = 334.2 (C.sub.22H.sub.19D.sub.4BO.sub.2 = 334.26) Sub1-19 m/z = 406.21 (C.sub.28H.sub.27BO.sub.2 = 406.33) Sub1-20 m/z = 410.24 (C.sub.28H.sub.23D.sub.4BO.sub.2 = 410.36) Sub1-21 m/z = 410.24 (C.sub.28H.sub.23D.sub.4BO.sub.2 = 410.36) Sub1-22 m/z = 406.21 (C.sub.28H.sub.27BO.sub.2 = 406.33) Sub1-23 m/z = 409.23 (C.sub.28H.sub.24D.sub.3BO.sub.2 = 409.35) Sub1-24 m/z = 406.21 (C.sub.28H.sub.27BO.sub.2 = 406.33) Sub1-25 m/z = 410.24 (C.sub.28H.sub.23D.sub.4BO.sub.2 = 410.36)

II. Synthesis of Sub2

[0092] Sub2 of Reaction Scheme 1 is synthesized by the reaction route of Reaction Scheme 2, but is not limited thereto.

##STR00044##

1. Synthesis Example of Sub2-1

[0093] ##STR00045##

[0094] After dissolving Sus2b-1 (13.9 g, 61.5 mmol) in THF (Tetrahydrofuran) (310 mL) in a round-bottom flask, Sub2a-1 (25.0 g, 61.5 mmol), NaOH (7.4 g, 184.6 mmol), Pd(PPh.sub.3).sub.4 (4.27 g, 3.69 mmol) and Water (155 mL) were added and stirred at 80° C. When the reaction was completed, the mixture was extracted with CH.sub.2Cl.sub.2 and water, and the organic layer was dried over MgSO.sub.4 and concentrated. The resulting compound was recrystallized by silicagel column to obtain 21.5 g (yield 74.5%) of the product.

2. Synthesis Example of Sub2-2

[0095] ##STR00046## ##STR00047##

(1) Synthesis Example of Sub2a-2

[0096] After dissolving Sub2d-2 (22.9 g, 69.4 mmol) in THF (350 mL) in a round-bottom flask, Sub2c-1 (20.0 g, 69.4 mmol), NaOH (8.3 g, 208.2 mmol), Pd(PPh.sub.3).sub.4 (4.81 g, 4.16 mmol) and Water (175 mL) were added, and 20.4 g (yield 71.4%) of the product was obtained by using the synthesis method of Sub2-1.

(2) Synthesis Example of Sub2-2

[0097] After dissolving Sub2b-1 (11.2 g, 49.5 mmol) in THF (250 mL) in a round-bottom flask, Sub2a-2 (20.4 g, 49.5 mmol), NaOH (5.9 g, 148.6 mmol), Pd(PPh.sub.3).sub.4 (3.44 g, 2.97 mmol) and Water (125 mL) were added, and 16.9 g (yield 71.7%) of the product was obtained by using the synthesis method of Sub2-1.

3. Synthesis Example of Sub2-9

[0098] ##STR00048##

[0099] After dissolving Sub2b-9 (13.0 g, 36.9 mmol) in THF (185 mL) in a round-bottom flask, Sub2a-1 (15.0 g, 36.9 mmol), NaOH (4.4 g, 110.7 mmol), Pd(PPh.sub.3).sub.4 (2.56 g, 2.21 mmol) and Water (92 mL) were added, and 16.1 g (yield 73.3%) of the product was obtained by using the synthesis method of Sub2-1.

4. Synthesis Example of Sub2-13

[0100] ##STR00049## ##STR00050## ##STR00051##

[0101] After dissolving Sub2b-13 (13.0 g, 36.9 mmol) in THF (185 mL) in a round-bottom flask, Sub2a-1 (15.0 g, 36.9 mmol), NaOH (4.4 g, 110.7 mmol), Pd(PPh.sub.3).sub.4 (2.56 g, 2.21 mmol) and Water (92 mL) were added, and 16.0 g (yield 72.7%) of the product was obtained by using the synthesis method of Sub2-1.

[0102] The compound belonging to Sub2 may be a compound as follows, but is not limited thereto, Table 2 below shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub2.

##STR00052## ##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057##

TABLE-US-00003 TABLE 2 compound FD-MS Sub2-1 m/z = 469.13 (C.sub.31H.sub.2CIN.sub.3 = 469.97) Sub2-2 m/z = 474.17 (C.sub.31H.sub.15D.sub.5CIN.sub.3 = 475.00) Sub2-3 m/z = 472.15 (C.sub.31H.sub.17D.sub.3CIN.sub.3 = 472.99) Sub2-4 m/z = 474.17 (C.sub.31H.sub.15D.sub.5CIN.sub.3 = 475.00) Sub2-5 m/z = 545.17 (C.sub.37H.sub.24CIN.sub.3 = 546.07) Sub2-6 m/z = 545.17 (C.sub.37H.sub.24CIN.sub.3 = 546.07) Sub2-7 m/z = 545.17 (C.sub.37H.sub.24CIN.sub.3 = 546.07) Sub2-8 m/z = 621.20 (C.sub.43H.sub.28CIN.sub.3 = 622.17) Sub2-9 m/z = 595.18 (C.sub.41H.sub.26CIN.sub.3 = 596.13) Sub2-10 m/z = 595.18 (C.sub.41H.sub.26CIN.sub.3 = 596.13) Sub2-11 m/z = 645.20 (C.sub.45H.sub.28CIN.sub.3 = 646.19) Sub2-12 m/z = 519.15 (C.sub.35H.sub.22CIN.sub.3 = 520.03) Sub2-13 m/z = 595.18 (C.sub.41H.sub.26CIN.sub.3 = 596.13) Sub2-14 m/z = 519.15 (C.sub.35H.sub.22CIN.sub.3 = 520.03) Sub2-15 m/z = 595.18 (C.sub.41H.sub.26CIN.sub.3 = 596.13) Sub2-16 m/z = 595.18 (C.sub.41H.sub.26CIN.sub.3 = 596.13) Sub2-17 m/z = 695.21 (C.sub.49H.sub.30CIN.sub.3 = 696.25) Sub2-18 m/z = 569.17 (C.sub.39H.sub.24CIN.sub.3 = 570.09) Sub2-19 m/z = 569.17 (C.sub.39H.sub.24CIN.sub.3 = 570.09)

III. Synthesis of Final Product

1. Synthesis Example of P-1

[0103] ##STR00058##

[0104] After dissolving Sus2-1 (5.0 g, 10.7 mmol) in THF (Tetrahydrofuran) (54 mL) in a round-bottom flask, Sub1-1 (3.0 g, 10.7 mmol), NaOH (1.3 g, 32.1 mmol), Pd(PPh.sub.3).sub.4 (0.74 g, 0.64 mmol) and Water (27 mL) were added and stirred at 80° C. When the reaction was completed, the mixture was extracted with CH2012 and water, and the organic layer was dried over MgSO.sub.4 and concentrated. The resulting compound was recrystallized by silicagel column to obtain 4.8 g (yield 77%) of the product.

2. Synthesis Example of P-8

[0105] ##STR00059##

[0106] After dissolving Sus2-1 (4.9 g, 10.5 mmol) in THF (Tetrahydrofuran) (53 mL) in a round-bottom flask, Sub1-3 (3.0 g, 10.5 mmol), NaOH (1.3 g, 31.6 mmol), Pd(PPh.sub.3).sub.4 (0.73 g, 0.63 mmol) and Water (26 mL) were added, and 4.6 g (yield 74%) of the product was obtained using the above synthesis method of P-1.

3. Synthesis Example of P-9

[0107] ##STR00060##

[0108] After dissolving Sus2-1 (5.0 g, 10.7 mmol) in THF (Tetrahydrofuran) (54 mL) in a round-bottom flask, Sub1-4 (3.0 g, 10.7 mmol), NaOH (1.3 g, 32.1 mmol), Pd(PPh.sub.3).sub.4 (0.74 g, 0.64 mmol) and Water (27 mL) were added, and 4.5 g (yield 71%) of the product was obtained using the above synthesis method of P-1.

4. Synthesis Example of P-16

[0109] ##STR00061##

[0110] After dissolving Sus2-10 (5.4 g, 9.1 mmol) in THF (Tetrahydrofuran) (45 mL) in a round-bottom flask, Sub1-5 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh.sub.3).sub.4 (0.63 g, 0.55 mmol) and Water (23 mL) were added, and 5.0 g (yield 72%) of the product was obtained using the above synthesis method of P-1.

5. Synthesis Example of P-19

[0111] ##STR00062##

[0112] After dissolving Sus2-1 (4.3 g, 9.1 mmol) in THF (Tetrahydrofuran) (45 mL) in a round-bottom flask, Sub1-7 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh.sub.3).sub.4 (0.63 g, 0.55 mmol) and Water (23 mL) were added, and 4.3 g (yield 75%) of the product was obtained using the above synthesis method of P-1.

6. Synthesis Example of P-22

[0113] ##STR00063##

[0114] After dissolving Sus2-1 (4.2 g, 8.9 mmol) in THF (Tetrahydrofuran) (45 mL) in a round-bottom flask, Sub1-9 (3.0 g, 8.9 mmol), NaOH (1.1 g, 26.8 mmol), Pd(PPh.sub.3).sub.4 (0.62 g, 0.54 mmol) and Water (22 mL) were added, and 4.2 g (yield 73%) of the product was obtained using the above synthesis method of P-1.

7. Synthesis Example of P-25

[0115] ##STR00064##

[0116] After dissolving Sus2-1 (4.3 g, 9.1 mmol) in THF (Tetrahydrofuran) (45 mL) in a round-bottom flask, Sub1-10 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh.sub.3).sub.4 (0.63 g, 0.55 mmol) and Water (23 mL) were added, and 4.5 g (yield 77%) of the product was obtained using the above synthesis method of P-1.

8. Synthesis Example of P-30

[0117] ##STR00065##

[0118] After dissolving Sus2-1 (4.0 g, 8.4 mmol) in THF (Tetrahydrofuran) (42 mL) in a round-bottom flask, Sub1-12 (3.0 g, 8.4 mmol), NaOH (1.0 g, 25.3 mmol), Pd(PPh.sub.3).sub.4 (0.58 g, 0.51 mmol) and Water (21 mL) were added, and 4.1 g (yield 74%) of the product was obtained using the above synthesis method of P-1.

9. Synthesis Example of P-34

[0119] ##STR00066##

[0120] After dissolving Sus2-2 (4.3 g, 9.1 mmol) in THF (Tetrahydrofuran) (45 mL) in a round-bottom flask, Sub1-15 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh.sub.3).sub.4 (0.63 g, 0.55 mmol) and Water (23 mL) were added, and 4.6 g (yield 78%) of the product was obtained using the above synthesis method of P-1.

10. Synthesis Example of P-40

[0121] ##STR00067##

[0122] After dissolving Sus2-6 (5.0 g, 9.1 mmol) in THF (Tetrahydrofuran) (45 mL) in a round-bottom flask, Sub1-16 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh.sub.3).sub.4 (0.63 g, 0.55 mmol) and Water (23 mL) were added, and 5.0 g (yield 77%) of the product was obtained using the above synthesis method of P-1.

11. Synthesis Example of P-42

[0123] ##STR00068##

[0124] After dissolving Sus2-6 (5.0 g, 9.1 mmol) in THF (Tetrahydrofuran) (45 mL) in a round-bottom flask, Sub1-17 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh.sub.3).sub.4 (0.63 g, 0.55 mmol) and Water (23 mL) were added, and 4.5 g (yield 70%) of the product was obtained using the above synthesis method of P-1.

[0125] Meanwhile, FD-MS values of compounds P-1 to P-44 of the present invention prepared according to the above synthesis examples are shown in Table 3.

TABLE-US-00004 TABLE 3 compound FD-MS P-1 m/z = 587.24 (C.sub.43H.sub.29N.sub.3 = 587.73) P-2 m/z = 637.25 (C.sub.47H.sub.31N.sub.3 = 637.79) P-3 m/z = 663.27 (C.sub.49H.sub.33N.sub.3 = 663.82) P-4 m/z = 592.27 (C.sub.43H.sub.24D.sub.5N.sub.3 = 592.76) P-5 m/z = 587.24 (C.sub.43H.sub.29N.sub.3 = 587.73) P-6 m/z = 587.24 (C.sub.43H.sub.29N.sub.3 = 587.73) P-7 m/z = 663.27 (C.sub.49H.sub.33N.sub.3 = 663.82) P-8 m/z = 663.27 (C.sub.49H.sub.33N.sub.3 = 663.82) P-9 m/z = 587.24 (C.sub.43H.sub.29N.sub.3 = 587.73) P-10 m/z = 663.27 (C.sub.49H.sub.33N.sub.3 = 663.82) P-11 m/z = 637.25 (C.sub.47H.sub.31N.sub.3 = 637.79) P-12 m/z = 590.25 (C.sub.43H.sub.26D.sub.3N.sub.3 = 590.74) P-13 m/z = 637.25 (C.sub.47H.sub.31N.sub.3 = 637.79) P-14 m/z = 737.28 (C.sub.55H.sub.35N.sub.3 = 737.91) P-15 m/z = 687.27 (C.sub.51H.sub.33N.sub.3 = 687.85) P-16 m/z = 763.3 (C.sub.57H.sub.37N.sub.3 = 763.94) P-17 m/z = 737.28 (C.sub.55H.sub.35N.sub.3 = 737.91) P-18 m/z = 713.28 (C.sub.53H.sub.35N.sub.3 = 713.88) P-19 m/z = 637.25 (C.sub.47H.sub.31N.sub.3 = 637.79) P-20 m/z = 642.28 (C.sub.47H.sub.26D.sub.5N.sub.3 = 642.82) P-21 m/z = 637.25 (C.sub.47H.sub.31N.sub.3 = 637.79) P-22 m/z = 642.28 (C.sub.47H.sub.26D.sub.5N.sub.3 = 642.82) P-23 m/z = 813.31 (C.sub.61H.sub.39N.sub.3 = 814) P-24 m/z = 763.3 (C.sub.57H.sub.37N.sub.3 = 763.94) P-25 m/z = 637.25 (C.sub.47H.sub.31N.sub.3 = 637.79) P-26 m/z = 642.28 (C.sub.47H.sub.26D.sub.5N.sub.3 = 642.82) P-27 m/z = 763.3 (C.sub.57H.sub.37N.sub.3 = 763.94) P-28 m/z = 713.28 (C.sub.53H.sub.35N.sub.3 = 713.88) P-29 m/z = 663.27 (C.sub.49H.sub.33N.sub.3 = 663.82) P-30 m/z = 667.29 (C.sub.49H.sub.29D.sub.4N.sub.3 = 667.85) P-31 m/z = 81 5.33 (C.sub.61H.sub.41N.sub.3 = 816.02) P-32 m/z = 713.28 (C.sub.53H.sub.35N.sub.3 = 713.88) P-33 m/z = 637.25 (C.sub.47H.sub.31N.sub.3 = 637.79) P-34 m/z = 642.28 (C.sub.47H.sub.26D.sub.5N.sub.3 = 642.82) P-35 m/z = 713.28 (C.sub.53H.sub.35N.sub.3 = 713.88) P-36 m/z = 642.28 (C.sub.47H.sub.26D.sub.5N.sub.3 = 642.82) P-37 m/z = 637.25 (C.sub.47H.sub.31N.sub.3 = 637.79) P-38 m/z = 763.3 (C.sub.57H.sub.37N.sub.3 = 763.94) P-39 m/z = 763.3 (C.sub.57H.sub.37N.sub.3 = 763.94) P-40 m/z = 713.28 (C.sub.53H.sub.35N.sub.3 = 713.88) P-41 m/z = 637.25 (C.sub.47H.sub.31N.sub.3 = 637.79) P-42 m/z = 713.28 (C.sub.53H.sub.35N.sub.3 = 713.88) P-43 m/z = 641.28 (C.sub.47H.sub.27D.sub.4N.sub.3 = 641.81) P-44 m/z = 863.33 (C.sub.65H.sub.41N.sub.3 = 864.06)

Evaluation of Manufacture of Organic Electronic Element

EXAMPLE 1

Red Organic Light Emitting Diode (Phosphorescent Host)

[0126] An organic electroluminescent device was manufactured according to a conventional method by using the compound obtained through synthesis as a emitting host material of the emitting layer. 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)-N1-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 -NPD) as a hole transport compound on the hole injection layer was vacuum-deposited to a thickness of 50 nm to form a hole transport layer.

[0127] An emitting auxiliary layer was formed by vacuum-depositing Tris(4-(9H-carbazol yl)phenyl)amine (hereinafter, TCTA) to a thickness of 10 nm as an emitting auxiliary layer material on the hole transport layer. After forming the emitting auxiliary layer, as a host on the emitting auxiliary layer, the compound P-1 of the present invention represented by Formula 1-1 and the compound C-1 were used in a weight ratio (5:5), and an emitting layer was deposited to a thickness of 30 nm by doping (piq).sub.2Ir(acac) as a dopant material in a 95:5 weight ratio. 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, bis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter, abbreviated as Alq3) was deposited to a thickness of 25 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 22

[0128] An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compounds of the present invention described in Table 4 were used instead of the compounds P-1 and C-1 of the present invention as host materials for the emitting layer.

COMPARATIVE EXAMPLE 1 TO COMPARATIVE EXAMPLE 3

[0129] An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound shown in Table 4 was used instead of the compound P-1 of the present invention as the host material of the emitting layer.

##STR00069## ##STR00070##

[0130] By applying a forward bias DC voltage to the organic electronic elements prepared in Examples 1 to 22 and Comparative Examples 1 to 3 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 2500 cd/m.sup.2 standard luminance. Table 4 shows the device fabrication and evaluation results.

TABLE-US-00005 TABLE 4 Current First Second Density Brightness Efficiency compound compound Voltage (mA/cm.sup.2) (cd/m.sup.2) (cd/A) T(95) comparative comparative compound 5.7 14.5 2500 17.3 96.5 example 1 compound (C-1) A comparative comparative compound 5.6 14.0 2500 17.9 102.6 example 2 compound (C-1) B comparative comparative compound 5.8 14.8 2500 16.9 97.7 example 3 compound (C-1) C example1 Compound compound 5.0 8.1 2500 30.9 130.6 (P-1) (C-1) example2 Compound compound 4.9 7.9 2500 31.7 126.2 (P-1) (C-2) example3 Compound compound 4.9 8.1 2500 30.8 130.6 (P-4) (C-1) example4 Compound compound 4.9 7.9 2500 31.7 126.2 (P-4) (C-2) example5 Compound compound 5.0 10.0 2500 24.9 129.3 (P-5) (C-1) example6 Compound compound 5.0 9.8 2500 25.6 125.0 (P-5) (C-2) example7 Compound compound 5.1 10.5 2500 23.8 126.8 (P-9) (C-1) example8 Compound compound 5.0 10.2 2500 24.4 122.6 (P-9) (C-2) example9 Compound compound 4.9 9.8 2500 25.4 135.7 (P-13) (C-1) example10 Compound compound 4.9 9.6 2500 26.1 131.1 (P-13) (C-2) example11 Compound compound 5.0 10.1 2500 24.7 131.8 (P-18) (C-1) example12 Compound compound 4.9 9.8 2500 25.4 127.4 (P-18) (C-2) example13 Compound compound 4.9 9.7 2500 25.9 133.1 (P-22) (C-1) example14 Compound compound 4.9 9.4 2500 26.6 128.6 (P-22) (C-2) example15 Compound compound 4.9 8.0 2500 31.3 140.6 (P-25) (C-1) example16 Compound compound 4.9 7.8 2500 32.2 136.0 (P-25) (C-2) example17 Compound compound 4.9 9.3 2500 26.8 128.0 (P-32) (C-1) example18 Compound compound 4.9 9.1 2500 27.6 123.7 (P-32) (C-2) example19 Compound compound 4.9 8.5 2500 29.5 138.2 (P-34) (C-1) example20 Compound compound 4.9 8.3 2500 30.3 133.5 (P-34) (C-2) example21 Compound compound 4.9 9.1 2500 27.5 135.6 (P-40) (C-1) example22 Compound compound 4.9 8.8 2500 28.3 131.2 (P-40) (C-2)

[0131] As can be seen from the results in Table 4, when the compound of the present invention is used as a host material for the emitting layer, it can be seen that the device performance is greatly improved compared to Comparative Examples 1 to 3.

[0132] When the compound of the present invention represented by Formula 1-1 is compared with Comparative Compounds A to C, the types of substituents bonded to triazines are different, and mobility varies depending on the types of substituents. In other words, the driving, efficiency, and lifespan are determined according to the degree of ease of injection of holes and electrons into the dopant, therefore when the hole and electron ratio (charge balance) is properly maintained, it is judged that the efficiency and lifespan are dramatically increased, which is expected to affect the charge balance according to the respective mobility levels of the first compound and the second compound.

[0133] As for the overall characteristics, in the case of the compounds of the present invention represented by Formula 1-1, the electron stability is high, and thus the electrical stability is high in comparison with the comparative compound, and thus a long lifespan characteristic. Comparing the compounds of the present invention, it can be seen that the device performance is determined according to the constituents of the compounds. In terms of driving voltage, it is highly dependent on the overall EOD and HOD, and it can be seen that this mobility is determined by the type of substituents the compound has, and that the efficiency aspect is determined by the electron hole balance of the heterogeneous compound. As a result, the performance of the device is greatly affected depending on the type and bonding position of the substituents substituted within the same backbone.

[0134] 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.