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 light-emitting efficiency, stability, and lifespan of an element; an organic electronic element using same; and an electronic device thereof.

Claims

1. A compound represented by Formula 1: ##STR00097## wherein: R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 being the same or different from each other, are each independently a hydrogen or deuterium, and a plurality of adjacent R.sup.4s or a plurality of adjacent R.sup.5s may be bonded to each other to form a benzene ring, wherein the benzene ring may be further substituted with one or more deuterium, a is an integer of 0 to 5, b is an integer of 0 to 6, c and e are independently an integer of 0 to 4, d is an integer of 0 to 3, Ar.sup.1 is hydrogen, phenyl substituted or unsubstituted with deuterium, or naphthyl substituted or unsubstituted with deuterium.

2. The compound of claim 1, wherein the compound represented by Formula 1 is any one of compounds P-1 to P-32: ##STR00098## ##STR00099## ##STR00100## ##STR00101## ##STR00102## ##STR00103## ##STR00104## ##STR00105##

3. A composition for an organic electronic element comprising a mixture of a compound according to claim 1 and a compound represented by Formula 4 or Formula 5: ##STR00106## wherein: L.sup.12, L.sup.13, L.sup.14 and L.sup.15 are each independently selected from the group consisting of a single bond; a C.sub.6-C.sub.60 arylene group; 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; Ar.sup.12, Ar.sup.13 and Ar.sup.14 are each independently selected from the group consisting of an C.sub.6-C.sub.60 aryl group; 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; Ar.sup.15 is selected from the group consisting of an C.sub.6-C.sub.60 aryl group; 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; and -LNRR; Y.sup.10 is O, S, CR.sup.51R.sup.52 or NR.sup.53, Ring B is an C.sub.6?C.sub.20 aryl group, R.sup.31 and R.sup.32 being the same or different from each other, are each independently selected from the group consisting of a hydrogen; deuterium; halogen; cyano group; an C.sub.6-C.sub.60 aryl group; 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; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.20 alkenyl group; a C.sub.2-C.sub.20 alkynyl group; a C.sub.1-C.sub.30 alkoxyl group; or a C.sub.6-C.sub.30 aryloxy group; and a plurality of adjacent R.sup.31s or a plurality of adjacent R.sup.32s may be bonded to each other to form a ring, R.sup.51, R.sup.52, R.sup.53, R and R are each independently selected from the group consisting of an C.sub.6-C.sub.60 aryl group; 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; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.20 alkenyl group; a C.sub.2-C.sub.20 alkynyl group; a C.sub.1-C.sub.30 alkoxyl group; and a C.sub.6-C.sub.30 aryloxy group; or R.sup.51 and R.sup.52 may be bonded to each other to form a ring, ba and bb are each independently an integer of 0 to 4, wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group and fused ring 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; C.sub.8-C.sub.20 arylalkenyl group; and -L-NRR; and 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.

4. The composition for an organic electronic element of claim 3, wherein the composition is for a host of an emitting layer.

5. The composition for an organic electronic element of claim 3, wherein the compound represented by Formula 4 are represented by any one of compounds H-1 to H-124: ##STR00107## ##STR00108## ##STR00109## ##STR00110## ##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118## ##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127## ##STR00128## ##STR00129## ##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134## ##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147##

6. The composition for an organic electronic element of claim 3, wherein the compound represented by Formula 5 are represented by any one of compounds S-1 to S-116: ##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161## ##STR00162## ##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171## ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179## ##STR00180##

7. An organic electronic element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises a compound of claim 1 or a composition of claim 3.

8. The organic electronic element of claim 7, wherein the organic electronic element further comprises a light efficiency enhancing layer formed on at least one surface of the first electrode and the second electrode, the surface being opposite to the organic material layer.

9. The organic electronic element of claim 7, wherein the organic material layer comprises 2 or more stacks comprising a hole transport layer, an emitting layer, and an electron transport layer sequentially formed on the first electrode.

10. The organic electronic element of claim 9, wherein the organic material layer further comprises a charge generation layer formed between the 2 or more stacks.

11. An electronic device comprising a display device comprising the organic electronic element of claim 7; and a control unit for driving the display device.

12. An electronic device of claim 11, wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photo conductor (OPC), organic transistor (organic TFT) and an element for monochromic or white illumination.

13. A method for reusing a compound of Formula 1 of claim 1 comprising: recovering a crude organic light emitting material comprising the compound of Formula 1 of claim 1 from a deposition apparatus used in the process for depositing the organic emitting material to prepare an organic an organic light emitting device; removing impurities from the crude organic light emitting material; recovering the organic light emitting material after the impurities are removed; and purifying the recovered organic light emitting material to have a purity of 99.9% or higher.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

(1) FIG. 1 to FIG. 3 are exemplary views of an organic electroluminescent device according to the present invention.

(2) FIG. 4 shows a formula according to one aspect of the present invention.

(3) TABLE-US-00001 Explanation of code 100, 200, 300: organic electronic 110: the first electrode 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

(4) 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.

(5) 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.

(6) As used in the specification and the accompanying claims, unless otherwise stated, the following is the meaning of the term as follows.

(7) Unless otherwise stated, the term halo or halogen, as used herein, includes fluorine, bromine, chlorine, or iodine.

(8) 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.

(9) 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.

(10) 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.

(11) Unless otherwise stated, the term alkoxyl group, alkoxy group or alkyloxy group, as used herein, means an alkyl group bonded to oxygen radical, but is not limited thereto, and has 1 to 60 carbon atoms.

(12) Unless otherwise stated, the term aryloxyl group or aryloxy group, as used herein, means an aryl group bonded to oxygen radical, but is not limited thereto, and has 6 to 60 carbon atoms.

(13) 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.

(14) For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

(15) 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.

(16) 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.

(17) 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.

(18) Unless otherwise stated, the term heteroatom, as used herein, represents at least one of N, O, S, P, or Si.

(19) 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.

(20) ##STR00003##

(21) 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.

(22) ##STR00004##

(23) 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.

(24) 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.

(25) 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.

(26) Other hetero compounds or hetero radicals other than the above-mentioned hetero compounds include, but are not limited thereto, one or more heteroatoms.

(27) 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.

(28) 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.

(29) ##STR00005##

(30) 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.

(31) ##STR00006##

(32) As used herein, the term composition is intended to be interpreted broadly, including compounds as well as solutions, dispersions, liquids and solid mixtures (mixture, admixture). The composition of the present invention may contain the compound of the present invention alone, or the compounds are contained in a combination of 2 or more different types, or the compounds may be contained in combinations of 2 or more types with other compounds. In other words, the composition may comprise a compound corresponding to Formula 1 alone, a mixture of 2 or more compounds of Formula 1, or a mixture of a compound of Formula 1 and a compound that does not correspond to the present invention. Wherein, the compound that does not correspond to the present invention may be a single compound, or may be 2 or more types of compounds. Here, if the compound is comprised in combination of 2 or more types of other compounds, wherein the other compounds may be already known compounds of each organic material layer, or may be compounds to be developed in the future. Here, the compound comprised in the organic material layer may consist of only the same type of compound, but may also be a mixture of 2 or more types of different compounds represented by Formula 1.

(33) Hereinafter, a compound according to one aspect of the present invention, a composition for a phosphorescent emitting layer of an organic electronic element, and an organic electronic element comprising the same will be described.

(34) The present invention provides a compound represented by Formula 1.

(35) ##STR00007## Wherein, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each the same or different, and each independently a hydrogen; or deuterium;

(36) Also, an adjacent plurality of R.sup.4s or a plurality of R.sup.5s may be bonded to each other to form a benzene ring, wherein the benzene ring may be further substituted with one or more deuterium, a is an integer from 0 to 5, b is an integer from 0 to 6, c and e are independently integers from 0 to 4, d is an integer from 0 to 3, Ar.sup.1 is hydrogen; phenyl substituted or unsubstituted with deuterium; or naphthyl substituted or unsubstituted with deuterium.

(37) Also, Formula 1 is represented by Formula 1-1 or Formula 1-2.

(38) ##STR00008## Wherein, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, a, b, c, d, e and Ar.sup.1 are as defined in Formula 1.

(39) Specifically, the compound of Formula 1 may be any one of the following compounds P-1 to P-32, but is not limited thereto.

(40) ##STR00009## ##STR00010## ##STR00011## ##STR00012## ##STR00013## ##STR00014## ##STR00015## ##STR00016##

(41) Also, in another aspect, the present invention provides a composition for a phosphorescent emitting layer of an organic electronic element comprising a mixture of a compound represented by Formula 1 and a compound represented by Formula 4 or Formula 5.

(42) ##STR00017## Wherein: L.sup.12, L.sup.13, L.sup.14 and L.sup.15 are each independently selected from the group consisting of a single bond; a C.sub.6-C.sub.60 arylene group; 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; Wherein in case L.sup.12, L.sup.13, L.sup.14 and L.sup.15 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.25 arylene group, for example, phenylene, biphenylene, naphthylene, terphenylene, anthracenylene, etc., Wherein in case L.sup.12, L.sup.13, L.sup.14 and L.sup.15 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, naphthobenzofuran, naphthobenzothiophene, benzocarbazole, etc. Wherein in case L.sup.12, L.sup.13, L.sup.14 and L.sup.15 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, Ar.sup.12, Ar.sup.13 and Ar.sup.14 are each independently selected from the group consisting of an C.sub.6-C.sub.60 aryl group; 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; Ar.sup.15 is selected from the group consisting of an C.sub.6-C.sub.60 aryl group; 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; and -L-NRR; Wherein in case Ar.sup.12, Ar.sup.13, Ar.sup.14 and Ar.sup.15 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 phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, chryshen, etc, Wherein in case Ar.sup.12, Ar.sup.13, Ar.sup.14 and Ar.sup.15 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, naphthobenzofuran, naphthobenzothiophene, benzocarbazole, etc. Wherein in case Ar.sup.12, Ar.sup.13, Ar.sup.14 and Ar.sup.15 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. Y.sup.10 is O, S, CR.sup.51R.sup.52 or NR.sup.53, Ring B is an C.sub.6?C.sub.20 aryl group, R.sup.31 and R.sup.32 are each independently the same or different, and each independently selected from the group consisting of a hydrogen; deuterium; halogen; cyano group; an C.sub.6-C.sub.60 aryl group; 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; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.20 alkenyl group; a C.sub.2-C.sub.20 alkynyl group; a C.sub.1-C.sub.30 alkoxyl group; and a C.sub.6-C.sub.30 aryloxy group; or an adjacent plurality of R.sup.31s or a plurality of R.sup.32s may be bonded to each other to form a ring, R.sup.51, R.sup.52, R.sup.53, R and R are each independently an C.sub.6-C.sub.60 aryl group; 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; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.20 alkenyl group; a C.sub.2-C.sub.20 alkynyl group; a C.sub.1-C.sub.30 alkoxyl group; and a C.sub.6-C.sub.30 aryloxy group; or R.sup.51 and R.sup.52 may be bonded to each other to form a ring, Wherein in case R.sup.31, R.sup.32, R.sup.51, R.sup.52, R.sup.53, R and R 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 phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc, Wherein in case R.sup.31, R.sup.32, R.sup.51, R.sup.52, R.sup.53, 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, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, naphthobenzofuran, naphthobenzothiophene, benzocarbazole, etc. Wherein in case R.sup.31, R.sup.32, R.sup.51, R.sup.52, R.sup.53, 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. Wherein in case R.sup.31, R.sup.32, R.sup.51, R.sup.52, R.sup.53, 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. Wherein in case R.sup.31, R.sup.32, R.sup.51, R.sup.52, R.sup.53, R and R are alkoxyl groups, they may be preferably C.sub.1?C.sub.24 alkoxyl groups, Wherein in case R.sup.31, R.sup.32, R.sup.51, R.sup.52, R.sup.53, R and R are an aryloxy group, it may be preferably an C.sub.6-C.sub.24 aryloxy, ba and bb are each independently an interger 0 to 4, wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group and fused ring 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; C.sub.8-C.sub.20 arylalkenyl group; and -L-NRR; and 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.

(43) Preferably, the composition for the phosphorescent emitting layer of the organic electronic element may be used as a host for the emitting layer.

(44) Formula 4 is represented by any one of Formulas 4-1 to 4-3.

(45) ##STR00018## Wherein: Ar.sup.13, Ar.sup.14, L.sup.12, L.sup.13 and L.sup.14 are as defined in Formula 4, X.sup.11, X.sup.12 and X.sup.13 are the same as definition of Y.sup.10 in Formula 5, R.sup.33, R.sup.34, R.sup.35, R.sup.36, R.sup.37 and R.sup.38 are each independently the same or different, and each independently selected from the group consisting of a hydrogen; 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; C.sub.8-C.sub.20 arylalkenyl group; or an adjacent plurality of R.sup.33 or of R.sup.34s or of R.sup.35s or of R.sup.36s or of R.sup.37s or of R.sup.38s may be bonded to each other to form a ring, bc, be, and bg are independently integers from 0 to 4, and bd, bf, and bh are independently integers from 0 to 3.

(46) Formula 5 is represented by any one of Formulas 5-1 to 5-6:

(47) ##STR00019## Wherein: Y.sup.10, Ar.sup.15, L.sup.15, R.sup.31, R.sup.32, ba and bb are the same as defined in Formula 5, R.sup.39 is each independently the same or different, and each independently selected from the group consisting of a hydrogen; 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; C.sub.3-C.sub.20 arylalkenyl group; or an adjacent plurality of R.sup.39 may be bonded to each other to form a ring, bi is an integer of 0 to 2.

(48) Formula 5 may be represented by any of the following Formulas 5-7 to 5-9:

(49) ##STR00020## Wherein: Y.sup.10, Ring B, Ar.sup.15, L.sup.15, R.sup.32 and bb are the same as defined in Formula 5, R.sup.40 is each independently the same or different, and each independently selected from the group consisting of a hydrogen; 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; C.sub.8-C.sub.20 arylalkenyl group; or an adjacent plurality of R.sup.40 may be bonded to each other to form a ring, bj is an integer of 0 to 6.

(50) Formula 5 may be represented by any of the following Formulas 5-10 to 5-12:

(51) ##STR00021## Wherein: Y.sup.10, Ring B, Ar.sup.15, L.sup.15, R.sup.31 and ba are the same as defined in Formula 5, R.sup.41 is each independently the same or different, and each independently selected from the group consisting of a hydrogen; 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; C.sub.8-C.sub.20 arylalkenyl group; or an adjacent plurality of R.sup.41 may be bonded to each other to form a ring, bk is an integer of 0 to 6.

(52) Formula 5 may be represented by any of the following Formulas 5-13 to 5-18:

(53) ##STR00022## Wherein: Y.sup.10, Ar.sup.15, L.sup.15, R.sup.31, R.sup.32, ba and bb are the same as defined in Formula 5, R.sup.39, R.sup.40 and R.sup.41 are each independently the same or different, and each independently selected from the group consisting of a hydrogen; 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; C.sub.8-C.sub.20 arylalkenyl group; or an adjacent plurality of R.sup.39, or plurality of R.sup.40, or plurality of R.sup.41 may be bonded to each other to form a ring, bi is an integer of 0 to 2, bj and bk are each independently an integer of 0 to 6.

(54) Formula 5 may be represented by Formula 5-19.

(55) ##STR00023## Wherein: Ar.sup.15, L.sup.15, R.sup.53, R.sup.32 and bb are the same as defined in Formula 5, R.sup.39 and R.sup.40 are each the same or different, and each independently selected from the group consisting of a hydrogen; 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; C.sub.8-C.sub.20 arylalkenyl group; or an adjacent plurality of R.sup.39, or plurality of R.sup.40 may be bonded to each other to form a ring, bi is an integer of 0 to 2, bj is an integer of 0 to 6.

(56) Specifically, the compound represented by Formula 4 may be any one of the following compounds H-1 to H-124, but is not limited thereto.

(57) ##STR00024## ##STR00025## ##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036## ##STR00037## ##STR00038## ##STR00039##

(58) Specifically, the compound represented by Formula 5 may be any one of the following compounds S-1 to S-116, but is not limited thereto.

(59) ##STR00040## ##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065## ##STR00066## ##STR00067## ##STR00068## ##STR00069## ##STR00070## ##STR00071##

(60) Also, in another aspect, the present invention relates to an organic electronic element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises a compound represented by Formula 1, or, a composition for a phosphorescent emitting layer of an organic electronic element comprising a mixture of the compound represented by Formula 1 and the compound represented by Formula 4 or Formula 5.

(61) In another aspect, the present invention provides a method for reusing the compound represented by Formula 1 comprising: recovering a crude organic light emitting material comprising the compound of Formula 1 of claim 1 from a deposition apparatus used in the process for depositing the organic emitting material to prepare an organic an organic light emitting device; removing impurities from the crude organic light emitting material; recovering the organic light emitting material after the impurities are removed; and purifying the recovered organic light emitting material to have a purity of 99.9% or higher.

(62) The step of removing impurities from the crude organic light emitting material recovered from the deposition apparatus may preferably comprise performing a pre-purification process to obtain a purity of 98% or more by recrystallization in a recrystallization solvent.

(63) The recrystallization solvent may be preferably a polar solvent having a polarity index (PI) of 5.5 to 7.2.

(64) The recrystallization solvent may be preferably used by mixing a polar solvent having a polarity value of 5.5 to 7.2 and a non-polar solvent having a polarity value of 2.0 to 4.7.

(65) When a mixture of a polar solvent and a non-polar solvent is used, the recrystallization solvent may be used in an amount of 15% (v/v) or less of the non-polar solvent compared to the polar solvent.

(66) The recrystallization solvent may preferably be used by mixing N-Methylpyrrolidone (NMP) single solvent; or a polar solvent mixed any one selected from the group consisting of 1,3-Dimethyl-2-imidazolidinone, 2-pyrrolidone, N, N-Dimethyl formamide, Dimethyl acetamide, and Dimethyl sulfoxide to the N-Methylpyrrolidone; or alone; or mixed non-polar solvents; selected from the group consisting of Toluene, Dichloromethane (DCM), Dichloroethane (DCE), Tetrahydrofuran (THF), Chloroform, Ethyl acetate and Butanone; or a polar solvent and a non-polar solvent.

(67) The pre-purification process may comprise a step of precipitating crystals of by cooling to 0? C. to 5? C. after dissolving the crude organic light emitting material recovered from the deposition apparatus in a polar solvent at 90? C. to 120? C.

(68) The pre-purification process may comprise a step of precipitating crystals by cooling to 35? C. to 40? C., adding a non-polar solvent, and then cooling to 0? C. to 5? C. after dissolving the crude organic light emitting material recovered from the deposition apparatus in a polar solvent at 90? C. to 120? C.

(69) The pre-purification process may comprise a step of precipitating crystals while concentrating the solvent and removing the non-polar solvent, after dissolving the crude organic light emitting material recovered from the deposition apparatus in a non-polar solvent.

(70) The pre-purification process may comprise a step of recrystallizing again with a non-polar solvent after recrystallizing first with a polar solvent.

(71) The step of purifying the recovered impurities to a purity of 99.9% or higher may comprise performing an adsorption separation process to adsorb and remove impurities by adsorbing on the adsorbent.

(72) The adsorbent may be activated carbon, silica gel, alumina, or a material for known adsorption purposes.

(73) The step of purifying the recovered impurities to a purity of 99.9% or higher may comprise performing sublimation purification

(74) Referring to FIG. 1, the organic electronic element (100) according to the present invention comprises a first electrode (110), a second electrode (170), an organic material layer comprising single compound represented by Formula 1 or 2 or more compounds between the first electrode (110) and the second electrode (170). Wherein, the first electrode (110) may be an anode or a positive electrode, and the second electrode (170) may be a cathode or a negative electrode. In the case of an inverted organic electronic element, the first electrode may be a cathode, and the second electrode may be an anode.

(75) The organic material layer may sequentially comprise 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) formed on the first electrode (110). Here, the remaining layers except the emitting layer (140) may not be formed. The organic material layer may further comprise 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).

(76) 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 a surface not in contact with the organic material layer among both surfaces of the first electrode or on a surface not in contact with the organic material layer among both surfaces of the second electrode. The compound according to an embodiment of the present invention applied to the organic material layer may be used as a material for a hole injection layer (120), a hole transport layer (130), an emitting-auxiliary layer (220), an electron transport auxiliary layer, an electron transport layer (150), an electron injection layer (160), a host or dopant of an emitting layer (140), or the light efficiency enhancing layer. Preferably, for example, the compound according to Formula 1 of the present invention, or a composition for a phosphorescent emitting layer of an organic electronic element comprising a mixture of a compound represented by Formula 1 and a compound represented by Formula 4 or Formula 5 may be used as a host material for the emitting layer.

(77) 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, and may further comprise a charge generation layer formed between the 2 or more stacks (see FIG. 3).

(78) Otherwise, even if the same core is used, the band gap, the electrical characteristics, the interface characteristics, and the like may vary depending on which substituent is bonded at which position, therefore the choice of core and the combination of sub-substituents associated therewith is 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 life span and high efficiency can be achieved at the same time.

(79) The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a PVD (physical vapor deposition) method. For example, a metal or a metal oxide having conductivity or an alloy thereof is deposited on a substrate to form a cathode, and the organic material layer comprising 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) is formed thereon, and then depositing a material usable as a cathode thereon can manufacture an organic electroluminescent device according to an embodiment of the present invention.

(80) Also, the present invention provides the organic electronic element wherein the organic material layer is formed by one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process, and the organic material layer provides an organic electronic element comprising the compound as an electron transport material.

(81) As another specific example, the present invention provides an organic electronic element used by mixing the same or different compounds of the compound represented by Formula 1 to the organic material layer. Preferably, the organic material layer includes an emitting layer, wherein the emitting layer may comprise a composition for a phosphorescent emitting layer of an organic electronic element comprising a compound represented by Formula 1, or a mixture of a compound represented by Formula 1 and a compound represented by Formula 4 or Formula 5.

(82) Also, the present invention provides a composition for a phosphorescent emitting layer of an organic electronic element comprising a compound represented by Formula 1, or a mixture of a compound represented by Formula 1 and a compound represented by Formula 4 or Formula 5, and provides an organic electronic element comprising the composition.

(83) Also, the present invention also provides an electronic device comprising a display device including the organic electronic element; and a control unit for driving the display device.

(84) According to another aspect, the present invention provides an display device wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photo conductor, an organic transistor (organic TFT) and an element for monochromic or white illumination. Here, the electronic device may be a wired/wireless communication terminal which is currently used or will be used in the future, and covers all kinds of electronic devices including a mobile communication terminal such as a cellular phone, 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.

(85) Hereinafter, Synthesis examples of the compound represented by Formula 1, Formula 4 and Formula 5 of the present invention and preparation examples of the organic electronic element of the present invention will be described in detail by way of example, but are not limited to the following examples.

EXAMPLES

Synthesis Example

(86) The compound (final products) represented by Formula 1 according to the present invention is synthesized by reacting Sub 1 and Sub 2 as in Reaction Scheme 1, but is not limited thereto.

(87) ##STR00072##

I. Synthesis of Sub 1

(88) Sub1 of Reaction Scheme 1 is synthesized by the reaction pathway of Reaction Scheme 2, but is not limited thereto.

(89) ##STR00073##

(90) Synthesis examples of specific compounds belonging to Sub 1 are as follows.

(91) ##STR00074##

(92) Sub1-1-1 (40.00 g, 111.34 mmol), 4,4,4,4,5,5,5,5-octamethyl-2,2-bi(1,3,2-dioxaborolane) (36.75 g, 144.74 mmol), Pd.sub.2(dppf)Cl.sub.2 (2.44 g, 3.34 mmol), KOAc (21.85 g, 222.67 mmol) were added to DMF (370 mL) in a round bottom flask, and stirred at 150? C. for 2 h. When the reaction was completed, the reaction solvent was removed and the concentrated organic material was recrystallized using a silicagel column to obtain 32.57 g (72%) of product Sub1-1.

(93) ##STR00075##

(1) Synthesis of Sub 1-2-1

(94) Sub1-2-1a (35.00 g, 121.44 mmol), (3-chlorophenyl)boronic acid (18.99 g, 121.44 mmol), Pd(PPh.sub.3).sub.4 (4.21 g, 3.64 mmol), K.sub.2CO.sub.3 (33.57 g, 242.89 mmol) were added to a round bottom flask, dissolved in 400 mL of anhydrous THE and 133 mL of water, and then refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH.sub.2Cl.sub.2 and water, and then treated with MgSO.sub.4. The product produced by concentrating the organic solvent was recrystallized using a silicagel column to obtain 29.13 g (75%) of Sub1-2-1.

(2) Synthesis of Sub 1-2

(95) Sub1-2-1 (28.00 g, 87.54 mmol), 4,4,4, 4, 5,5,5, 5-octamethyl-2,2-bi(1,3,2-dioxaborolane) (28.90 g, 113.81 mmol), Pd.sub.2(dba).sub.3 (2.40 g, 2.63 mmol), Xphos (2.50 g, 5.25 mmol), KOAc (17.18 g, 175.09 mmol) were added to DMF (290 mL) in a round bottom flask, and stirred at 150? C. for 2 h. When the reaction was completed, the reaction solvent was removed and the concentrated organic material was recrystallized using a silicagel column to obtain 24.48 g (68%) of product Sub1-2.

(96) ##STR00076##

(1) Synthesis of Sub 1-3-1

(97) Sub1-3-1a (38.00 g, 153.17 mmol), 1-bromo-3-chlorobenzene-d4 (29.94 g, 153.17 mmol), Pd(PPh.sub.3).sub.4 (5.31 g, 4.60 mmol), K.sub.2CO.sub.3 (42.34 g, 306.34 mmol) were placed in a round bottom flask, dissolved in anhydrous THE (510 mL) and water (170 mL) and then refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH.sub.2Cl.sub.2 and water, and then treated with MgSO.sub.4. The product produced by concentrating the organic solvent was recrystallized using a silicagel column to obtain 35.65 g (73%) of Sub1-3-1.

(2) Synthesis of Sub 1-3

(98) Sub1-3-1 (32.00 g, 100.36 mmol), 4,4,4, 4, 5,5,5, 5-octamethyl-2,2-bi(1,3,2-dioxaborolane) (33.13 g, 130.47 mmol), Pd.sub.2(dba).sub.3 (2.76 g, 3.01 mmol), Xphos (2.87 g, 6.02 mmol), KOAc (19.70 g, 200.73 mmol) were added to DMF (335 mL) in a round bottom flask, and stirred at 150? C. for 2 h. When the reaction was completed, the reaction solvent was removed and the concentrated organic material was recrystallized using a silicagel column to obtain 27.59 g (67%) of product Sub1-3.

(99) ##STR00077##

(1) Synthesis of Sub 1-4-1

(100) Sub1-4-1a (35.00 g, 118.95 mmol), (3-chlorophenyl)boronic acid (18.60 g, 118.95 mmol), Pd(PPh.sub.3).sub.4 (4.13 g, 3.57 mmol), K.sub.2CO.sub.3 (32.88 g, 237.90 mmol) were placed in a round bottom flask, dissolved in anhydrous THE (396 mL) and water (132 mL) and then refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH.sub.2Cl.sub.2 and water, and then treated with MgSO.sub.4. The product produced by concentrating the organic solvent was recrystallized using a silicagel column to obtain 29.07 g (75%) of Sub1-4-1.

(2) Synthesis of Sub 1-4

(101) Sub1-4-1 (26.00 g, 79.78 mmol), 4,4,4, 4, 5,5,5, 5-octamethyl-2,2-bi(1,3,2-dioxaborolane) (26.34 g, 103.72 mmol), Pd.sub.2(dba).sub.3 (2.19 g, 2.39 mmol), Xphos (2.28 g, 4.79 mmol), KOAc (15.66 g, 159.57 mmol) were added to DMF (266 mL) in a round bottom flask, and stirred at 150? C. for 2 h. When the reaction was completed, the reaction solvent was removed and the concentrated organic material was recrystallized using a silicagel column to obtain 27.31 g (82%) of product Sub1-4.

(102) ##STR00078##

(103) Sub1-6-1 (40.00 g, 106.85 mmol), 4,4,4, 4, 5,5,5, 5-octamethyl-2,2-bi(1,3,2-dioxaborolane) (35.27 g, 138.90 mmol), Pd.sub.2(dppf)Cl.sub.2 (2.35 g, 3.21 mmol), KOAc (20.97 g, 213.70 mmol) were added to DMF (365 mL) in a round bottom flask, and stirred at 150? C. for 2 h. When the reaction was completed, the reaction solvent was removed and the concentrated organic material was recrystallized using a silicagel column to obtain 30.62 g (68%) of product Sub1-6.

(104) Meanwhile, the compounds belonging to Sub 1 may be the following compounds, but are not limited thereto, and Table 1 shows the FD-MS (Field Desorption-Mass Spectrometry) values of the compounds belonging to Sub 1.

(105) ##STR00079## ##STR00080##

II. Synthesis of Sub 2

(106) TABLE-US-00002 TABLE 1 com- com- pound FD-MS pound FD-MS Sub1-1 m/z = 406.21(C.sub.28H.sub.27BO.sub.2 = 406.33) Sub1-2 m/z = 411.24(C.sub.28H.sub.22D.sub.5BO.sub.2 = 411.36) Sub1-3 m/z = 410.24(C.sub.28H.sub.23D.sub.4BO.sub.2 = 410.36) Sub1-4 m/z = 417.28(C.sub.28H.sub.16D.sub.11BO.sub.2 = 417.4) Sub1-5 m/z = 412.25(C.sub.28H.sub.21D.sub.6BO.sub.2 = 412.37) Sub1-6 m/z = 421.3(C.sub.28H.sub.12D.sub.15BO.sub.2 = 421.42) Sub1-7 m/z = 416.27(C.sub.28H.sub.17D.sub.10BO.sub.2 = 416.39)

(107) Sub 2 of Reaction Scheme 1 is synthesized by the reaction pathway of Reaction Scheme 3, but is not limited thereto.

(108) ##STR00081##

(109) Synthesis examples of specific compounds belonging to Sub 2 are as follows.

(110) ##STR00082##

(111) Sub2-2-1 (83.34 g, 368.65 mmol), Sub2-2-a (33.00 g, 184.33 mmol), Pd(PPh.sub.3).sub.4 (6.39 g, 5.53 mmol), K.sub.2CO.sub.3 (50.95 g, 368.65 mmol) were added to a round bottom flask, dissolved in anhydrous THE (615 mL) and water (205 mL), and then refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH.sub.2Cl.sub.2 and water, and then treated with MgSO.sub.4. The product produced by concentrating the organic solvent was recrystallized using a silicagel column to obtain 25.15 g (42%) of Sub2-2.

(112) ##STR00083##

(113) Sub2-5-1 (92.54 g, 335.14 mmol), Sub2-2-a (30.00 g, 167.57 mmol), Pd(PPh.sub.3).sub.4 (5.81 g, 5.03 mmol), K.sub.2CO.sub.3 (46.32 g, 335.14 mmol) were added to a round bottom flask, dissolved in anhydrous THE (558 mL) and water (186 mL), and then refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH.sub.2Cl.sub.2 and water, and then treated with MgSO.sub.4. The product produced by concentrating the organic solvent was recrystallized using a silicagel column to obtain 23.87 g (38%) of Sub2-5.

(114) ##STR00084##

(115) Sub2-2-1 (39.13 g, 173.09 mmol), Sub2-10-a (20.00 g, 86.54 mmol), Pd(PPh.sub.3).sub.4 (3.00 g, 2.60 mmol), K.sub.2CO.sub.3 (23.92 g, 173.09 mmol) were added to a round bottom flask, dissolved in anhydrous THE (288 mL) and water (96 mL), and then refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH.sub.2Cl.sub.2 and water, and then treated with MgSO.sub.4. The product produced by concentrating the organic solvent was recrystallized using a silicagel column to obtain 15.00 g (46%) of Sub2-10.

(116) ##STR00085##

(117) Sub2-12-1 (83.26 g, 360.28 mmol), Sub2-12-a (40.00 g, 180.14 mmol), Pd(PPh.sub.3).sub.4 (6.25 g, 5.40 mmol), K.sub.2CO.sub.3 (46.79 g, 360.28 mmol) were added to a round bottom flask, dissolved in anhydrous THE (600 mL) and water (200 mL), and then refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH.sub.2Cl.sub.2 and water, and then treated with MgSO.sub.4. The product produced by concentrating the organic solvent was recrystallized using a silicagel column to obtain 28.88 g (43%) of Sub2-12.

(118) ##STR00086##

(119) Sub2-16-1 (77.12 g, 279.28 mmol), Sub2-16-a (25.00 g, 139.64 mmol), Pd(PPh.sub.3).sub.4 (4.84 g, 4.19 mmol), K.sub.2CO.sub.3 (38.60 g, 279.28 mmol) were added to a round bottom flask, dissolved in anhydrous THE (465 mL) and water (155 mL), and then refluxed for 12 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH.sub.2Cl.sub.2 and water, and then treated with MgSO.sub.4. The product produced by concentrating the organic solvent was recrystallized using a silicagel column to obtain 27.22 g (52%) of Sub2-16.

(120) Meanwhile, the compounds belonging to Sub 2 may be the following compounds, but are not limited thereto, and Table 2 shows the FD-MS (Field Desorption-Mass Spectrometry) values of the compounds belonging to Sub 2.

(121) ##STR00087## ##STR00088## ##STR00089## ##STR00090##

(122) TABLE-US-00003 TABLE 2 com- com- pound FD-MS pound FD-MS Sub2-1 m/z = 317.07(C.sub.19H.sub.12ClN.sub.3 = 317.78) Sub2-2 m/z = 324.12(C.sub.19H.sub.5D.sub.7ClN.sub.3 = 324.82) Sub2-3 m/z = 322.1(C.sub.19H.sub.7D.sub.5ClN.sub.3 = 322.81) Sub2-4 m/z = 324.12(C.sub.19H.sub.5D.sub.7ClN.sub.3 = 324.82) Sub2-5 m/z = 374.13(C.sub.23H.sub.7D.sub.7ClN.sub.3 = 374.88) Sub2-6 m/z = 381.18(C.sub.23D.sub.14ClN.sub.3 = 381.92) Sub2-7 m/z = 374.13(C.sub.23H.sub.7D.sub.7ClN.sub.3 = 374.88) Sub2-8 m/z = 367.09(C.sub.23H.sub.14ClN.sub.3 = 367.84) Sub2-9 m/z = 367.09(C.sub.23H.sub.14ClN.sub.3 = 367.84) Sub2-10 m/z = 376.14(C.sub.23H.sub.5D.sub.9ClN.sub.3 = 376.89) Sub2-11 m/z = 367.09(C.sub.23H.sub.14ClN.sub.3 = 367.84) Sub2-12 m/z = 372.12(C.sub.23H.sub.9D.sub.5ClN.sub.3 = 372.87) Sub2-13 m/z = 417.1(C.sub.27H.sub.16ClN.sub.3 = 417.9) Sub2-14 m/z = 424.15(C.sub.27H.sub.9D.sub.7ClN.sub.3 = 424.94) Sub2-15 m/z = 426.16(C.sub.27H.sub.7D.sub.9ClN.sub.3 = 426.95) Sub2-16 m/z = 374.13(C.sub.23H.sub.7D.sub.7ClN.sub.3 = 374.88)

III. Synthesis of Final Product

(123) ##STR00091##

(124) Sub1-1 (15.00 g, 36.92 mmol), Sub2-1 (11.73 g, 36.92 mmol), Pd(PPh.sub.3).sub.4 (1.28 g, 1.11 mmol), NaOH (2.95 g, 73.83 mmol) and THE (120 mL) and water (40 mL) were added, and reacted at 75? C. for 8 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature and the reaction solvent is removed. Afterwards, the concentrated reactant was recrystallized using a Silicagel column to obtain 16.17 g (78%) of product P-1.

(125) ##STR00092##

(126) Sub1-1 (18.00 g, 44.30 mmol), Sub2-5 (16.61 g, 44.30 mmol), Pd(PPh.sub.3).sub.4 (1.54 g, 1.33 mmol), NaOH (3.54 g, 88.60 mmol) and THE (150 mL) and water (50 mL) were added, and reacted at 75? C. for 8 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature and the reaction solvent is removed. Afterwards, the concentrated reactant was recrystallized using a Silicagel column to obtain 20.28 g (74%) of product P-10.

(127) ##STR00093##

(128) Sub1-2 (17.00 g, 41.33 mmol), Sub2-8 (15.20 g, 41.33 mmol), Pd(PPh.sub.3).sub.4 (1.43 g, 1.24 mmol), NaOH (3.31 g, 82.65 mmol) and THE (138 mL) and water (46 mL) were added, and reacted at 75? C. for 8 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature and the reaction solvent is removed. Afterwards, the concentrated reactant was recrystallized using a Silicagel column to obtain 17.33 g (68%) of product P-13.

(129) ##STR00094##

(130) Sub1-4 (12.00 g, 28.75 mmol), Sub2-8 (10.58 g, 28.75 mmol), Pd(PPh.sub.3).sub.4 (1.00 g, 0.86 mmol), NaOH (2.30 g, 57.50 mmol) and THE (96 mL) and water (32 mL) were added, and reacted at 75? C. for 8 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature and the reaction solvent is removed. Afterwards, the concentrated reactant was recrystallized using a Silicagel column to obtain 13.61 g (76%) of product P-15.

(131) ##STR00095##

(132) Sub1-1 (14.00 g, 34.54 mmol), Sub2-10 (13.02 g, 34.54 mmol), Pd(PPh.sub.3).sub.4 (1.20 g, 1.04 mmol), NaOH (2.76 g, 69.08 mmol) and THE (115 mL) and water (38 mL) were added, and reacted at 75? C. for 8 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature and the reaction solvent is removed. Afterwards, the concentrated reactant was recrystallized using a Silicagel column to obtain 15.44 g (72%) of product P-27.

(133) Meanwhile, the FD-MS values of compounds P-1 to P-32 of the present invention prepared according to the above synthesis examples are shown in Table 3.

(134) TABLE-US-00004 TABLE 3 com- com- pound FD-MS pound FD-MS P-1 m/z = 561.22(C.sub.41H.sub.27N.sub.3 = 561.69) P-2 m/z = 566.25(C.sub.41H.sub.22D.sub.5N.sub.3 = 566.72) P-3 m/z = 568.26(C.sub.41H.sub.20D.sub.7N.sub.3 = 568.73) P-4 m/z = 566.25(C.sub.41H.sub.22D.sub.5N.sub.3 = 566.72) P-5 m/z = 573.3(C.sub.41H.sub.15D.sub.12N.sub.3 = 573.76) P-6 m/z = 572.29(C.sub.41H.sub.16D.sub.11N.sub.3 = 572.76) P-7 m/z = 565.25(C.sub.41H.sub.23D.sub.4N.sub.3 = 565.71) P-8 m/z = 618.28(C.sub.45H.sub.22D.sub.7N.sub.3 = 618.79) P-9 m/z = 625.32(C.sub.45H.sub.15D.sub.14N.sub.3 = 625.83) P-10 m/z = 618.28(C.sub.45H.sub.22D.sub.7N.sub.3 = 618.79) P-11 m/z = 611.24(C.sub.45H.sub.29N.sub.3 = 611.75) P-12 m/z = 623.31(C.sub.45H.sub.17D.sub.12N.sub.3 = 623.82) P-13 m/z = 616.27(C.sub.45H.sub.24D.sub.5N.sub.3 = 616.78) P-14 m/z = 611.24(C.sub.45H.sub.29N.sub.3 = 611.75) P-15 m/z = 622.31(C.sub.45H.sub.18D.sub.11N.sub.3 = 622.82) P-16 m/z = 616.27(C.sub.45H.sub.24D.sub.5N.sub.3 = 616.78) P-17 m/z = 615.26(C.sub.45H.sub.25D.sub.4N.sub.3 = 615.77) P-18 m/z = 620.29(C.sub.45H.sub.20D.sub.9N.sub.3 = 620.8) P-19 m/z = 617.27(C.sub.45H.sub.23D.sub.6N.sub.3 = 617.78) P-20 m/z = 616.27(C.sub.45H.sub.24D.sub.5N.sub.3 = 616.78) P-21 m/z = 616.27(C.sub.45H.sub.24D.sub.5N.sub.3 = 616.78) P-22 m/z = 615.26(C.sub.45H.sub.25D.sub.4N.sub.3 = 615.77) P-23 m/z = 620.29(C.sub.45H.sub.20D.sub.9N.sub.3 = 620.8) P-24 m/z = 616.27(C.sub.45H.sub.24D.sub.5N.sub.3 = 616.78) P-25 m/z = 620.29(C.sub.45H.sub.20D.sub.9N.sub.3 = 620.8) P-26 m/z = 617.27(C.sub.45H.sub.23D.sub.6N.sub.3 = 617.78) P-27 m/z = 620.29(C.sub.45H.sub.20D.sub.9N.sub.3 = 620.8) P-28 m/z = 611.24(C.sub.45H.sub.29N.sub.3 = 611.75) P-29 m/z = 666.28(C.sub.49H.sub.26D.sub.5N.sub.3 = 666.84) P-30 m/z = 674.33(C.sub.49H.sub.18D.sub.13N.sub.3 = 674.89) P-31 m/z = 666.28(C.sub.49H.sub.26D.sub.5N.sub.3 = 666.84) P-32 m/z = 670.31(C.sub.49H.sub.22D.sub.9N.sub.3 = 670.86)

(135) The compound represented by Formula 4 or Formula 5 may be prepared by referring to a known synthesis method (named reaction), or published patent publications, such as Korean Patent Publication No. 10-2395819, US Patent Publication No. 2023-0129535, etc. but is not limited thereto.

(136) Meanwhile, the FD-MS values of compounds H-1 to H-124 and S-1 to S-116 of the present invention are shown in Tables 4 and 5.

(137) TABLE-US-00005 TABLE 4 com- com- pound FD-MS pound FD-MS H-1 m/z = 487.19(C.sub.36H.sub.25NO = 487.6) H-2 m/z = 553.19(C.sub.40H.sub.27NS = 553.72) H-3 m/z = 563.26(C.sub.43H.sub.33N = 563.74) H-4 m/z = 602.27(C.sub.45H.sub.34N.sub.2 = 602.78) H-5 m/z = 517.15(C.sub.36H.sub.23NOS = 517.65) H-6 m/z = 603.2(C.sub.44H.sub.29NS = 603.78) H-7 m/z = 735.29(C.sub.57H.sub.37N = 735.93) H-8 m/z = 562.24(C.sub.42H.sub.30N.sub.2 = 562.72) H-9 m/z = 565.17(C.sub.40H.sub.23NO.sub.3 = 565.63) H-10 m/z = 581.14(C.sub.40H.sub.23NO.sub.2S = 581.69) H-11 m/z = 823.24(C.sub.59H.sub.37NS.sub.2 = 824.07) H-12 m/z = 727.3(C.sub.54H.sub.37N.sub.3 = 727.91) H-13 m/z = 627.22(C.sub.46H.sub.29NO.sub.2 = 627.74) H-14 m/z = 633.16(C.sub.44H.sub.27NS.sub.2 = 633.83) H-15 m/z = 675.29(C.sub.52H.sub.37N = 675.88) H-16 m/z = 678.3(C.sub.51H.sub.38N.sub.2 = 678.88) H-17 m/z = 669.21(C.sub.48H.sub.31NOS = 669.84) H-18 m/z = 785.22(C.sub.56H.sub.35NS.sub.2 = 786.02) H-19 m/z = 617.18(C.sub.44H.sub.27NOS = 617.77) H-20 m/z = 601.2(C.sub.44H.sub.27NO.sub.2 = 601.71) H-21 m/z = 779.32(C.sub.59H.sub.41NO = 779.98) H-22 m/z = 583.23(C.sub.42H.sub.33NS = 583.79) H-23 m/z = 679.32(C.sub.52H.sub.41N = 679.91) H-24 m/z = 726.27(C.sub.54H.sub.34N.sub.2O = 726.88) H-25 m/z = 593.18(C.sub.42H.sub.27NOS = 593.74) H-26 m/z = 774.22(C.sub.54H.sub.34N.sub.2S.sub.2 = 775) H-27 m/z = 557.24(C.sub.40H.sub.31NO.sub.2 = 557.69) H-28 m/z = 652.25(C.sub.48H.sub.32N.sub.2O = 652.8) H-29 m/z = 619.29(C.sub.46H.sub.37NO = 619.81) H-30 m/z = 603.2(C.sub.44H.sub.29NS = 603.78) H-31 m/z = 813.3(C.sub.62H.sub.39NO = 814) H-32 m/z = 784.29(C.sub.57H.sub.40N.sub.2S = 785.02) H-33 m/z = 577.2(C.sub.42H.sub.27NO.sub.2 = 577.68) H-34 m/z = 607.14(C.sub.42H.sub.25NS.sub.2 = 607.79) H-35 m/z = 801.34(C.sub.62H.sub.43N = 802.03) H-36 m/z = 575.24(C.sub.42H.sub.29N.sub.3 = 575.72) H-37 m/z = 577.2(C.sub.42H.sub.27NO.sub.2 = 577.68) H-38 m/z = 607.14(C.sub.42H.sub.25NS.sub.2 = 607.79) H-39 m/z = 801.34(C.sub.62H.sub.43N = 802.03) H-40 m/z = 575.24(C.sub.42H.sub.29N.sub.3 = 575.72) H-41 m/z = 601.2(C.sub.44H.sub.27NO.sub.2 = 601.71) H-42 m/z = 471.11(C.sub.31H.sub.21NS.sub.2 = 471.64) H-43 m/z = 675.29(C.sub.52H.sub.37N = 675.88) H-44 m/z = 727.3(C.sub.54H.sub.37N.sub.3 = 727.91) H-45 m/z = 603.2(C.sub.44H.sub.29NS = 603.78) H-46 m/z = 561.16(C.sub.38H.sub.27NS.sub.2 = 561.76) H-47 m/z = 799.32(C.sub.62H.sub.41N = 800.02) H-48 m/z = 702.27(C.sub.52H.sub.34N.sub.2O = 702.86) H-49 m/z = 729.27(C.sub.54H.sub.35NO.sub.2 = 729.88) H-50 m/z = 785.22(C.sub.56H.sub.35NS.sub.2 = 786.02) H-51 m/z = 812.32(C.sub.62H.sub.40N.sub.2 = 813.02) H-52 m/z = 681.22(C.sub.48H.sub.31N.sub.3S = 681.86) H-53 m/z = 615.18(C.sub.44H.sub.25NO.sub.3 = 615.69) H-54 m/z = 763.15(C.sub.52H.sub.29NS.sub.3 = 763.99) H-55 m/z = 593.31(C.sub.45H.sub.39N = 593.81) H-56 m/z = 840.33(C.sub.62H.sub.40N.sub.4 = 841.03) H-57 m/z = 657.18(C.sub.46H.sub.27NO.sub.2S = 657.79) H-58 m/z = 824.23(C.sub.58H.sub.36N.sub.2S.sub.2 = 825.06) H-59 m/z = 1195.42(C.sub.91H.sub.57NS = 1196.52) H-60 m/z = 656.19(C.sub.46H.sub.28N.sub.2OS = 656.8) H-61 m/z = 607.16(C.sub.42H.sub.25NO.sub.2S = 607.73) H-62 m/z = 773.2(C.sub.54H.sub.31NO.sub.3S = 773.91) H-63 m/z = 1013.4(C.sub.79H.sub.51N = 1014.28) H-64 m/z = 758.24(C.sub.54H.sub.34N.sub.2OS = 758.94) H-65 m/z = 623.14(C.sub.42H.sub.25NOS.sub.2 = 623.79) H-66 m/z = 763.16(C.sub.52H.sub.29NO.sub.2S.sub.2 = 763.93) H-67 m/z = 799.2(C.sub.56H.sub.33NOS.sub.2 = 800.01) H-68 m/z = 743.23(C.sub.54H.sub.33NOS = 743.92) H-69 m/z = 872.25(C.sub.62H.sub.36N.sub.2O.sub.2S = 873.04) H-70 m/z = 772.22(C.sub.54H.sub.32N.sub.2O.sub.2S = 772.92) H-71 m/z = 830.28(C.sub.61H.sub.38N.sub.2S = 831.05) H-72 m/z = 808.25(C.sub.58H.sub.33FN.sub.2O.sub.2 = 808.91) H-73 m/z = 929.21(C.sub.64H.sub.35NO.sub.3S.sub.2 = 930.11) H-74 m/z = 963.27(C.sub.68H.sub.41N.sub.3S.sub.2 = 964.22) H-75 m/z = 809.24(C.sub.58H.sub.35NO.sub.2S = 809.98) H-76 m/z = 893.29(C.sub.66H.sub.39NO.sub.3 = 894.04) H-77 m/z = 794.28(C.sub.58H.sub.38N.sub.2S = 795.02) H-78 m/z = 900.26(C.sub.64H.sub.40N.sub.2S.sub.2 = 901.16) H-79 m/z = 758.28(C.sub.55H.sub.38N.sub.2S = 758.98) H-80 m/z = 1082.37(C.sub.81H.sub.50N.sub.2S = 1083.37) H-81 m/z = 573.25(C.sub.44H.sub.31N = 573.74) H-82 m/z = 649.28(C.sub.50H.sub.35N = 649.84) H-83 m/z = 699.29(C.sub.54H.sub.37N = 699.9) H-84 m/z = 699.29(C.sub.54H.sub.37N = 699.9) H-85 m/z = 673.28(C.sub.52H.sub.35N = 673.86) H-86 m/z = 649.28(C.sub.50H.sub.35N = 649.84) H-87 m/z = 625.28(C.sub.48H.sub.35N = 625.82) H-88 m/z = 673.28(C.sub.52H.sub.35N = 673.86) H-89 m/z = 773.31(C.sub.60H.sub.39N = 773.98) H-90 m/z = 749.31(C.sub.58H.sub.39N = 749.96) H-91 m/z = 699.29(C.sub.54H.sub.37N = 699.9) H-92 m/z = 599.26(C.sub.46H.sub.33N = 599.78) H-93 m/z = 639.26(C.sub.48H.sub.33NO = 639.8) H-94 m/z = 765.25(C.sub.57H.sub.35NS = 765.97) H-95 m/z = 677.31(C.sub.52H.sub.39N = 677.89) H-96 m/z = 727.3(C.sub.54H.sub.37N.sub.3 = 727.91) H-97 m/z = 552.18(C.sub.39H.sub.24N.sub.2O.sub.2 = 552.63) H-98 m/z = 628.22(C.sub.45H.sub.28N.sub.2O.sub.2 = 628.73) H-99 m/z = 614.24(C.sub.45H.sub.30N.sub.2O = 614.75) H-100 m/z = 614.24(C.sub.45H.sub.30N.sub.2O = 614.75) H-101 m/z = 691.21(C.sub.50H.sub.29NO.sub.3 = 691.79) H-102 m/z = 739.29(C.sub.56H.sub.37NO = 739.92) H-103 m/z = 673.15(C.sub.46H.sub.27NOS.sub.2 = 673.85) H-104 m/z = 726.27(C.sub.54H.sub.34N.sub.2O = 726.88) H-105 m/z = 617.18(C.sub.44H.sub.27NOS = 617.77) H-106 m/z = 611.22(C.sub.46H.sub.29NO = 611.74) H-107 m/z = 769.24(C.sub.56H.sub.35NOS = 769.96) H-108 m/z = 701.28(C.sub.52H.sub.35N.sub.3 = 701.87) H-109 m/z = 527.22(C.sub.39H.sub.29NO = 527.67) H-110 m/z = 643.2(C.sub.46H.sub.29NOS = 643.8) H-111 m/z = 593.18(C.sub.42H.sub.27NOS = 593.74) H-112 m/z = 726.27(C.sub.54H.sub.34N.sub.2O = 726.88) H-113 m/z = 726.27(C.sub.54H.sub.34N.sub.2O = 726.88) H-114 m/z = 558.14(C.sub.37H.sub.22N.sub.2O.sub.2S = 558.65) H-115 m/z = 620.19(C.sub.43H.sub.28N.sub.2OS = 620.77) H-116 m/z = 686.27(C.sub.52H.sub.34N.sub.2 = 686.86) H-117 m/z = 718.24(C.sub.52H.sub.34N.sub.2S = 718.92) H-118 m/z = 728.28(C.sub.54H.sub.36N.sub.2O = 728.89) H-119 m/z = 592.2(C.sub.42H.sub.28N.sub.2S = 592.76) H-120 m/z = 756.22(C.sub.54H.sub.32N.sub.2OS = 756.92) H-121 m/z = 547.70(C.sub.42H.sub.29N = 547.70) H-122 m/z = 672.28(C.sub.49H.sub.24D.sub.7NO.sub.2 = 672.83) H-123 m/z = 626.28(C.sub.48H.sub.26D.sub.5N = 558.75) H-124 m/z = 558.22(C.sub.40H.sub.22D.sub.5NS = 558.75)

(138) TABLE-US-00006 TABLE 5 com- com- pound FD-MS pound FD-MS S-1 m/z = 408.16(C.sub.30H.sub.20N.sub.2 = 408.5) S-2 m/z = 534.21(C.sub.40H.sub.26N.sub.2 = 534.66) S-3 m/z = 560.23(C.sub.42H.sub.28N.sub.2 = 560.7) S-4 m/z = 584.23(C.sub.44H.sub.28N.sub.2 = 584.72) S-5 m/z = 560.23(C.sub.42H.sub.28N.sub.2 = 560.7) S-6 m/z = 634.24(C.sub.48H.sub.30N.sub.2 = 634.78) S-7 m/z = 610.24(C.sub.46H.sub.30N.sub.2 = 610.76) S-8 m/z = 498.17(C.sub.36H.sub.22N.sub.2O = 498.59) S-9 m/z = 574.2(C.sub.42H.sub.26N.sub.2O = 574.68) S-10 m/z = 660.26(C.sub.50H.sub.32N.sub.2 = 660.82) S-11 m/z = 686.27(C.sub.52H.sub.34N.sub.2 = 686.86) S-12 m/z = 620.14(C.sub.42H.sub.24N.sub.2S.sub.2 = 620.79) S-13 m/z = 640.2(C.sub.46H.sub.28N.sub.2S = 640.8) S-14 m/z = 560.23(C.sub.42H.sub.28N.sub.2 = 560.7) S-15 m/z = 558.21(C.sub.42H.sub.26N.sub.2 = 558.68) S-16 m/z = 548.19(C.sub.40H.sub.24N.sub.2O = 548.65) S-17 m/z = 573.22(C.sub.42H.sub.27N.sub.3 = 573.7) S-18 m/z = 564.17(C.sub.40H.sub.24N.sub.2S = 564.71) S-19 m/z = 574.2(C.sub.42H.sub.26N.sub.2O = 574.68) S-20 m/z = 564.17(C.sub.40H.sub.24N.sub.2S = 564.71) S-21 m/z = 564.17(C.sub.40H.sub.24N.sub.2S = 564.71) S-22 m/z = 813.31(C.sub.61H.sub.39N.sub.3 = 814) S-23 m/z = 696.26(C.sub.53H.sub.32N.sub.2 = 696.85) S-24 m/z = 691.23(C.sub.49H.sub.29N.sub.3O.sub.2 = 691.79) S-25 m/z = 710.27(C.sub.54H.sub.34N.sub.2 = 710.88) S-26 m/z = 610.24(C.sub.46H.sub.30N.sub.2 = 610.76) S-27 m/z = 670.15(C.sub.46H.sub.26N.sub.2S.sub.2 = 670.85) S-28 m/z = 640.29(C.sub.48H.sub.36N.sub.2 = 640.83) S-29 m/z = 598.2(C.sub.44H.sub.26N.sub.2O = 598.71) S-30 m/z = 623.24(C.sub.46H.sub.29N.sub.3 = 623.76) S-31 m/z = 458.18(C.sub.34H.sub.22N.sub.2 = 458.56) S-32 m/z = 548.19(C.sub.40H.sub.24N.sub.2O = 548.65) S-33 m/z = 508.19(C.sub.38H.sub.24N.sub.2 = 508.62) S-34 m/z = 508.19(C.sub.38H.sub.24N.sub.2 = 508.62) S-35 m/z = 623.24(C.sub.46H.sub.29N.sub.3 = 623.76) S-36 m/z = 564.17(C.sub.40H.sub.24N.sub.2S = 564.71) S-37 m/z = 627.2(C.sub.46H.sub.29NS = 627.81) S-38 m/z = 505.1(C.sub.34H.sub.19NS.sub.2 = 505.65) S-39 m/z = 514.15(C.sub.36H.sub.22N.sub.2S = 514.65) S-40 m/z = 575.17(C.sub.42H.sub.25NS = 575.73) S-41 m/z = 642.21(C.sub.46H.sub.30N.sub.2S = 642.82) S-42 m/z = 575.17(C.sub.42H.sub.25NS = 575.73) S-43 m/z = 606.18(C.sub.42H.sub.26N.sub.2OS = 606.74) S-44 m/z = 575.17(C.sub.42H.sub.25NS = 575.73) S-45 m/z = 551.17(C.sub.40H.sub.25NS = 551.71) S-46 m/z = 607.14(C.sub.42H.sub.25NS.sub.2 = 607.79) S-47 m/z = 525.16(C.sub.38H.sub.23NS = 525.67) S-48 m/z = 642.21(C.sub.46H.sub.30N.sub.2S = 642.82) S-49 m/z = 548.19(C.sub.40H.sub.24N.sub.2O = 548.65) S-50 m/z = 473.14(C.sub.34H.sub.19NO.sub.2 = 473.53) S-51 m/z = 566.15(C.sub.39H.sub.22N.sub.2OS = 566.68) S-52 m/z = 459.16(C.sub.34H.sub.21NO = 459.55) S-53 m/z = 473.14(C.sub.34H.sub.19NO.sub.2 = 473.53) S-54 m/z = 523.16(C.sub.38H.sub.21NO.sub.2 = 523.59) S-55 m/z = 539.13(C.sub.38H.sub.21NOS = 539.65) S-56 m/z = 548.19(C.sub.40H.sub.24N.sub.2O = 548.65) S-57 m/z = 489.12(C.sub.34H.sub.19NOS = 489.59) S-58 m/z = 545.09(C.sub.36H.sub.19NOS.sub.2 = 545.67) S-59 m/z = 549.17(C.sub.40H.sub.23NO.sub.2 = 549.63) S-60 m/z = 565.15(C.sub.40H.sub.23NOS = 565.69) S-61 m/z = 523.16(C.sub.38H.sub.21NO.sub.2 = 523.59) S-62 m/z = 598.2(C.sub.44H.sub.26N.sub.2O = 598.71) S-63 m/z = 539.13(C.sub.38H.sub.21NOS = 539.65) S-64 m/z = 589.15(C.sub.42H.sub.23NOS = 589.71) S-65 m/z = 498.17(C.sub.36H.sub.22N.sub.2O = 498.59) S-66 m/z = 509.18(C.sub.38H.sub.23NO = 509.61) S-67 m/z = 548.19(C.sub.40H.sub.24N.sub.2O = 548.65) S-68 m/z = 549.17(C.sub.40H.sub.23NO.sub.2 = 549.63) S-69 m/z = 449.12(C.sub.32H.sub.19NS = 449.57) S-70 m/z = 439.1(C.sub.30H.sub.17NOS = 439.53) S-71 m/z = 647.22(C.sub.49H.sub.29NO = 647.78) S-72 m/z = 717.28(C.sub.52H.sub.35N.sub.3O = 717.87) S-73 m/z = 459.16(C.sub.34H.sub.21NO = 459.55) S-74 m/z = 533.18(C.sub.40H.sub.23NO = 533.63) S-75 m/z = 525.16(C.sub.38H.sub.23NS = 525.67) S-76 m/z = 564.17(C.sub.40H.sub.24N.sub.2S = 564.71) S-77 m/z = 575.19(C.sub.42H.sub.25NO.sub.2 = 575.67) S-78 m/z = 663.22(C.sub.49H.sub.29NO.sub.2 = 663.78) S-79 m/z = 647.22(C.sub.49H.sub.29NO = 647.78) S-80 m/z = 496.16(C.sub.36H.sub.20N.sub.2O = 496.57) S-81 m/z = 565.15(C.sub.40H.sub.23NOS = 565.69) S-82 m/z = 505.1(C.sub.34H.sub.19NS.sub.2 = 505.65) S-83 m/z = 765.25(C.sub.56H.sub.35NOSi = 765.99) S-84 m/z = 615.17(C.sub.44H.sub.25NOS = 615.75) S-85 m/z = 603.17(C.sub.43H.sub.25NOS = 603.74) S-86 m/z = 772.29(C.sub.59H.sub.36N.sub.2 = 772.95) S-87 m/z = 802.33(C.sub.61H.sub.42N.sub.2 = 803.02) S-88 m/z = 607.23(C.sub.47H.sub.29N = 607.76) S-89 m/z = 524.23(C.sub.39H.sub.28N.sub.2 = 524.67) S-90 m/z = 665.22(C.sub.49H.sub.31NS = 665.85) S-91 m/z = 633.25(C.sub.49H.sub.31N = 633.79) S-92 m/z = 775.29(C.sub.59H.sub.37NO = 775.95) S-93 m/z = 535.23(C.sub.41H.sub.29N = 535.69) S-94 m/z = 623.22(C.sub.47H.sub.29NO = 623.76) S-95 m/z = 687.2(C.sub.51H.sub.29NS = 687.86) S-96 m/z = 735.29(C.sub.57H.sub.37N = 735.93) S-97 m/z = 611.26(C.sub.47H.sub.33N = 611.79) S-98 m/z = 679.23(C.sub.50H.sub.33NS = 679.88) S-99 m/z = 787.32(C.sub.61H.sub.41N = 788.01) S-100 m/z = 743.33(C.sub.55H.sub.41N.sub.3 = 743.95) S-101 m/z = 485.21(C.sub.37H.sub.27N = 485.63) S-102 m/z = 471.2(C.sub.36H.sub.25N = 471.6) S-103 m/z = 571.19(C.sub.43H.sub.25NO = 571.68) S-104 m/z = 584.23(C.sub.44H.sub.28N.sub.2 = 584.72) S-105 m/z = 539.24(C.sub.40H.sub.21D.sub.5N.sub.2 = 539.69) S-106 m/z = 453.15(C.sub.32H.sub.15NS = 471.6) S-107 m/z = 563.26(C.sub.43H.sub.26D.sub.4NO = 563.74) S-108 m/z = 589.26(C.sub.44H.sub.23D.sub.5N.sub.2 = 584.72) S-109 m/z = 589.26(C.sub.44H.sub.23D.sub.5N.sub.2 = 589.75) S-110 m/z = 562.23(C.sub.42H.sub.22D.sub.4N.sub.2 = 562.71) S-111 m/z = 660.26(C.sub.50H.sub.32N.sub.2 = 660.82) S-112 m/z = 553.22(C.sub.40H.sub.19D.sub.5N.sub.2O = 553.68) S-113 m/z = 634.24(C.sub.48H.sub.30N.sub.2 = 634.78) S-114 m/z = 589.26(C.sub.44H.sub.23D.sub.5N.sub.2 = 589.75) S-115 m/z = 588.25(C.sub.44H.sub.24D.sub.4N.sub.2 = 588.75) S-116 m/z = 513.23(C.sub.38H.sub.19D.sub.5N.sub.2 = 513.65)

(139) Otherwise, the synthesis examples of the present invention represented by Formula 1, Formula 4 and Formula 5 have been described, but these are all based on the Buchwald-Hartwig cross coupling reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, Intramolecular acid-induced cyclization reaction (J. mater. Chem. 1999, 9, 2095.), Pd(II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504), and PPh.sub.3-mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014.), and it will be easily understood by those skilled in the art that the reaction proceeds even when other substituents defined in Formula 1, Formula 4 and Formula 5 are bonded in addition to the substituents specified in the specific synthesis examples.

(140) [Manufacturing Evaluation of Organic Electronic Elements]

[Example 1] Red Organic Light Emitting Device (Phosphorescent Host)

(141) Compound A and Compound B were used on the ITO layer (anode) formed on a glass substrate, and a hole injection layer with a thickness of 10 nm was formed by doping Compound B at a weight ratio of 98:2, and then Compound A was vacuum deposited to a thickness of 110 nm on the hole injection layer to form a hole transport layer.

(142) Next, compound CR was vacuum deposited to a thickness of 10 nm on the hole transport layer to form an emitting auxiliary layer. Thereafter, the host material of the emitting layer uses compound P-1 of the present invention as the first host and compound H-19 of the present invention as the second host, and a mixture of the first host and the second host in a weight ratio of 5:5 is used, and bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter abbreviated as (piq)2lr(acac)) was used as a dopant material, and an emitting layer with a thickness of 30 nm was formed by doping the dopant so that the weight ratio of the host to the dopant was 95:5.

(143) Next, Compound E is vacuum deposited on the emitting layer to form a hole blocking layer with a thickness of 10 nm, and an electron transport layer with a thickness of 30 nm was formed on the hole blocking layer using a mixture of Compound F and Compound G in a weight ratio of 5:5. Afterwards, Compound G was deposited on the electron transport layer to form an electron injection layer with a thickness of 0.2 nm, and then Al was deposited to form a cathode with a thickness of 150 nm.

(144) Compound A: N-([1,1-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

(145) Compound B: 4,4, 4-((1E,1E,1E)-cyclopropane-1,2,3-triylidenetris(cyanomethaneylylidene))tris(2,3,5,6-tetrafluorobenzonitrile)

(146) Compound CR: N.sup.7-(dibenzo[b,d]thiophen-2-yl)-N.sup.2,N.sup.2,N.sup.7-triphenyldibenzo[b,d]thiophene-2,7-diamine

(147) Compound E: 2-(4-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine

(148) Compound F: 2,7-bis(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalene

(149) Compound G: (8-quinolinolato)lithium

[Example 2] to [Example 26]

(150) An organic electroluminescent device was manufactured in the same manner as Example 1, except that the compound of the present invention shown in Table 6 was used as the host material of the emitting layer.

[Comparative Example 1] and [Comparative Example 2]

(151) An organic electroluminescent device was manufactured in the same manner as Example 1, except that Comparative Compound A and Comparative Compound B below were used as the first host materials of the emitting layer.

(152) ##STR00096##

(153) To the organic electroluminescent device manufactured by Examples 1 to 26 of the present invention, Comparative Examples 1 and 2, Electroluminescence (EL) characteristics were measured with a PR-650 of Photoresearch Co., by applying a forward bias DC voltage. As a result of the measurement, T95 life was measured at a standard luminance of 2,500 cd/m.sup.2 through life measuring apparatus manufactured by McScience. Table 6 shows the results of device fabrication and evaluation.

(154) This measuring device is independent form possible day-to-day variations of deposition rates, vacuum quality or other tool performance parameters, and allows assessing performance of new material in comparison with comparative compound under the same conditions.

(155) At the time of assessment, each field contained 4 identically prepared OLEDs including a comparative compound, and since the performance of each of a total of 12 OLEDs in 3 fields is evaluated, the statistical evaluation of the obtained experimental results unequivocally showed the statistical significance.

(156) TABLE-US-00007 TABLE 6 Current Second Density Efficiency First First host host Voltage (mA/cm.sup.2) (cd/A) compound T(95) Comparative Comparative H-19 5.3 11.6 2500.0 21.5 91.2 example 1 compound A Comparative Comparative H-19 5.5 12.0 2500.0 20.9 90.1 example 2 compound B Example 1 P-1 H-19 4.2 7.1 2500.0 35.0 127.7 Example 2 P-3 H-19 4.1 6.8 2500.0 36.5 129.0 Example 3 P-5 H-19 4.1 5.9 2500.0 42.2 133.8 Example 4 P-8 H-19 4.1 6.0 2500.0 41.9 129.6 Example 5 P-10 H-19 4.2 6.0 2500.0 42.0 134.0 Example 6 P-14 H-19 4.2 6.1 2500.0 41.0 129.5 Example 7 P-16 H-19 4.2 5.6 2500.0 44.3 132.2 Example 8 P-17 H-19 4.2 5.7 2500.0 43.9 134.7 Example 9 P-21 H-19 4.3 5.8 2500.0 42.9 133.7 Example 10 P-30 H-19 4.1 5.8 2500.0 43.0 133.4 Example 11 P-3 H-97 4.1 6.6 2500.0 37.9 130.0 Example 12 P-5 H-97 4.1 6.4 2500.0 39.2 132.5 Example 13 P-16 H-97 4.2 5.7 2500.0 43.7 135.0 Example 14 P-1 H-121 4.2 6.8 2500.0 36.8 130.3 Example 15 P-14 H-121 4.3 5.6 2500.0 44.8 132.7 Example 16 P-21 H-121 4.3 6.8 2500.0 36.9 129.9 Example 17 P-1 S-16 4.4 6.2 2500.0 40.2 137.5 Example 18 P-8 S-16 4.4 5.9 2500.0 42.7 143.7 Example 19 P-30 S-16 4.5 6.7 2500.0 37.4 140.4 Example 20 P-3 S-110 4.5 6.0 2500.0 41.6 137.6 Example 21 P-5 S-110 4.4 5.9 2500.0 42.3 139.6 Example 22 P-10 S-110 4.4 6.1 2500.0 40.8 137.8 Example 23 P-14 S-110 4.5 6.5 2500.0 38.5 140.5 Example 24 P-16 S-110 4.3 5.6 2500.0 45.0 144.8 Example 25 P-17 S-110 4.3 5.6 2500.0 44.9 145.0 Example 26 P-21 S-110 4.5 6.4 2500.0 39.2 143.2

(157) As can be seen from the results of Table 6, when a red organic light emitting device is manufactured using the material for an organic light emitting device of the present invention as a host material of the emitting layer, the driving voltage, luminous efficiency, and lifespan of the organic electroluminescent device can be improved compared to the comparative example using Comparative Compound A or Comparative Compound B, which has a similar basic structure to the compound of the present invention.

(158) Comparative Compound A and Comparative Compound B have similar compositions to the compounds of the present invention, but Comparative Compound A and Comparative Compound B are different from the compounds of the present invention in that they contain a heterocyclic group or a cyano group.

(159) In order to confirm the difference in the energy level of the compound due to this difference, the data measured using the DFT method (B3LYP/6-31g(D)) of the Gaussian program is shown in Table 7.

(160) TABLE-US-00008 TABLE 7 Comparative Comparative compound A compound B P-8 HOMO(eV) ?5.8770 ?5.8458 ?5.5547 LUMO(eV) ?2.0792 ?2.2694 ?1.9075 T1(eV) 2.4961 2.4729 2.4274

(161) As can be seen from the results in Table 7, it can be seen that the energy levels of the compounds of the present invention and the comparative compounds are formed differently.

(162) To explain in more detail, Comparative Compound A and Comparative Compound B have a structure containing a heterocyclic group or a cyano group, which creates a deep LUMO energy level and causes excessive electron injection into the emitting layer, which breaks the charge balance of the element. On the contrary, the compound of the present invention has a LUMO energy level that is the intermediate value between the electron transport region and the dopant of the emitting layer, so it can prevent electrons in the electron transport region from accumulating directly into the dopant of the emitting layer, and it is easy to form an exciplex between the first host and the second host. Moreover, the compound of the present invention, which has a lower T1 energy level compared to the comparative compounds, transfers energy from the host to the dopant more easily than the comparative compounds, resulting in less damage when energy is transferred from the host to the dopant, which is believed to significantly improve device lifespan.

(163) That is, as can be seen from the results in Tables 6 and 7, even if it is a compound with a similar composition, it can be confirmed that the compound of the present invention, which satisfies all complex factors such as the type of specific substituent and the substitution position of the substituent, shows a remarkable effect compared to other comparative compounds in organic electronic elements, and through this, it can be seen that the compound of the present invention exhibits a more significant effect in organic electronic elements than simple structural isomers or compounds with similar compositions not described in this description.

(164) These results show that even in compounds with similar molecular components, the properties of the compound, such as the hole characteristics of the molecule, characteristics of light efficiency, energy level, characteristics of hole injection and mobility, charge balance of holes and electrons, volume density and the distance between molecules can vary significantly to the extent that it is difficult to predict, depending on the type and substitution position of the substituent being substituted, and additionally, it suggests that one configuration does not affect the results of the entire element, but that the performance of the element can vary due to complex factors.

(165) 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.

(166) 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.