TW200846348A - Imidazopyridine-based compound and organic light emitting diode including organic layer comprising the imidazopyridine-based compound - Google Patents

Abstract

Imidazopyridine-based compounds and organic light emitting diodes (OLEDs) including organic layers including the imidazopyridine-based compounds are provided. The organic light emitting diodes including organic layers having the imidazopyridine-based compounds have low driving voltages, high efficiencies, high luminance, long life-times and low power consumption.

Description

200846348 IX. Description of the invention: [Technical field to which the invention pertains] Cross-reference to the related application This application claims Korean patent application filed at the Private Country Intellectual Property Office on November 24, 2006 and July 24, 2007, respectively. The priority and the benefit of the second and third of the sequel are to be incorporated herein by reference. TECHNICAL FIELD The present invention relates to an imidazole pyridine-based compound and an organic light-emitting diode (OLEDs) of an organic layer containing a compound of a sulphonium-based compound. More specifically, the present invention is directed to an imidazole pyridine-based compound suitable for an electron-transporting layer of an organic light-emitting diode, and an organic light-emitting diode of an organic layer containing an imidazole pyridine-based compound.

* Organic Light Emitting Diodes (0LEDs) are self-illuminating diodes with a 觅 viewing angle, excellent contrast, and fast response times. The organic light-emitting diode has a good reaction time and can obtain a multi-color image. Shellness, operating voltage and in conventional organic light-emitting diodes

A pole is continuously formed on the anode. The hole transport layer and the organic film formed. Yes 6 200846348 When a voltage is applied across the anode and cathode, the hole injected from the anode is transferred from the same transmission layer to the luminescent layer. Electrons injected from the cathode are transmitted via f sub =

To the luminescent layer. The holes and electrons are recombined with each other in the light-emitting layer to generate a hair. When the excitons fall from the excited state to the ground state, the fluorescent molecules of the light-emitting layer emit light. Heteroaromatic compounds such as oxadiazole, oxadiazole, pyrimidine and the like can be used as the material for forming the electron transport layer. However, conventional organic light-emitting diodes do not have satisfactory driving voltage, brightness, current density, power factor, lifetime, and the like. SUMMARY OF THE INVENTION According to one embodiment of the present invention, there is a high electron transport capability. The imidazopyridine-based compound has a compound which is mainly composed of imidazopyridine, a low driving voltage, a high luminance, and in another embodiment of the present invention, the organic light-emitting diode has a high efficiency and a long life.

The compound according to the specific aspect of the present invention " Equation 1 (R 丄一 ΛΓ1

In Equation 1, ? And q are respectively selected from integers from 1 to 5, 'Gu and η are selected from 〇 to 1 R, to 4 integers, and m*n are not 0. 1, 3 R4 ' R5 ' R6 ' and heart respectively 7 200846348 from a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted crc3 () alkyl group, a substituted or unsubstituted CrC3G alkoxy group, substituted Or unsubstituted clc3() fluorenyl group, substituted or unsubstituted C2-C3G alkenyl group, substituted or unsubstituted C2_C30 fast group, substituted or unsubstituted c6- a c30 aryl group and a substituted or unsubstituted c3-c30 heteroaryl group. At least two of r4, R5, R6 and R7 are bonded to each other to form a saturated or unsaturated ring. At least two of R9, R1G, Rn and are bonded to each other to form a saturated or unsaturated ring. And L2 may be independently selected from a single bond, a substituted or unsubstituted Ci_C3g alkylene group, a substituted or unsubstituted c6-C3G extended aryl group, and a substituted or unsubstituted heteroaryl group. Group. Ari and Ar2 may be independently selected from a substituted or unsubstituted CfCw aryl group and a substituted or unsubstituted C3-C3() heteroaryl group. According to another embodiment of the present invention, the organic light emitting diode (1) lED) includes a first electrode, a second electrode, and an organic layer between the first and second electrodes, the organic layer comprising a scorpion bite Compound. The imidazopyridine-based compound represented by Formula 1 has high electron transporting ability, so that the organic light-emitting diode of the organic layer containing the imidazopyridine-based compound can have a low driving voltage, a high current density, a high sound rate, and a long life. . h. High efficiency [Embodiment] Detailed Description of the Invention The following formula 1 shows a compound according to the specific state of the present invention. Magical pyrazole is 200846348 Formula 1

As shown in Formula 1, L1 or h is bonded to the gamma ring at at least one of the i-th to eighth positions of the ankle ring instead of the ninth or first 〇 position of the ring. The imidazole pyridine ring has not been blocked. 〇 σ is in the 9th or 1st position of Grace.

Placed because the 9th and 1st position are structurally fragile points. Therefore, when the ninth and the first center of the anthracene ring are substituted with a group having a specific function, the group may be easily decomposed by hydrazine, hydrogen, milk or the like. For example, when the imidazole pyridine ring (^ or the Μ#要社人*'s) is combined with the ninth ge:... of the 1 ring, it may be reported as easy to use in the form, ^, sperm, child product or similar The heat generated during the process is such that the imidazolium ring and the anthracene ring are divided into 97. During the process of finely illuminating the organic light-emitting diode, the properties of the imidazolium ring-opening window diode may also be deteriorated. Iron, but the solution, so that the organic light. Sitting on acridine-based human ", according to the specific aspect of the present invention, the scorpion fish hn fragrant 4' such as an aryl group or a heteroaryl group ... β. In addition, the imidazole pyridine ring (it lacks Electron) is combined with at least one position of the 〗 ring to the 8th position of the 弟. Therefore, the imidazole pyridine is mainly a compound sub-flow. L, has & good structural stability and electricity in the formula 1, R 〖, R2, R3 Rn and R!2 are respectively selected from a hydrogen atom group, a substituted or unsubstituted, R4, R5, R6, r7, r8, r9, Ri., a halogen atom, a hydroxyl group, a cyano group. a C1 C3 G alkyl group, a Ci-Cw alkoxy group substituted or not substituted by 9 200846348, a substituted or unsubstituted Ci_CM thiol group, a substituted or unsubstituted C2_CS() olefin a radical, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted c Γ 6 ^"30 aryl group, and a substituted or unsubstituted C3_CM heteroaryl group. At least two of R5, R0 and R7 are combined with each other to form a saturated or unsaturated bad 'and I, R1G, R" and at least two of them combine to form a full Or an unsaturated ring. • In a specific aspect, h to Ru may be independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted C2-c10 alkenyl group. a substituted or unsubstituted aryl group and a substituted or unsubstituted c3-ci2 heteroaryl group. According to another embodiment, R4, Rs, 1 and at least two of the cores, or R9 And at least two of R1G, Rn and are bonded to each other to form a substituted or unsubstituted C6-C12 aromatic ring. In Formula 1, hydrazine and L2 may be respectively selected from a single bond, substituted or unsubstituted _ a CrCw alkylene group, a substituted or unsubstituted c6-c3() extended aryl group, and a substituted or unsubstituted c3_c3g heteroaryl group. In a specific evil sample, L And L2 may be respectively selected from a substituted or unsubstituted c6_cu aryl group and a substituted or unsubstituted heteroaryl group. In Formula 1, ΑΓ ι and A. may be respectively selected from A substituted or unsubstituted CdG aryl group and a substituted or unsubstituted C3_c" heteroaryl group. In a particular sad form, for example, Aq and may be selected from substituted or unsubstituted C6_Cl2 aryl groups and substituted or unsubstituted C3_200846348 C" 2 heteroaryl groups, respectively. Chemical structure

In Formula 1, P and q are each selected from an integer from 丨 to 5. In a physical form, for example, p# is an integer from ^3. That is, at least one imidazole pyridine ring may be bonded to one or L2, which may be, or L, in Formula 1, wherein the paw and n are each selected from an integer from 〇 to 4, but neither ❿ nor η are zero. That is, in the compound mainly composed of imidazopyridine according to the present invention, at least one of the i- to 帛8 positions of the anthracene ring is bonded to the sulphur-salt ring. In a specific aspect, for example. Maybe 疋11 and 可1. In another embodiment, both melon and n may be one. In the compounds represented by Formula 1, non-limiting examples of suitable unsubstituted CrCSG alkyl groups used include methyl groups, ethyl groups, propyl groups, isobutyl groups, Di-butyl group, pentyl group, iso-pentyl group, hexyl group and the like. Any one selected from the group consisting of a self atom, a hydroxyl group, a nitro group, a cyano group, an amine group, a thiol group, a hydrazine, a hydrazine, a carboxyl group or a salt thereof, a sulfonic acid group or a salt, a phosphate group or a salt thereof, a cvcw alkyl group, a 〇2弋30 alkenyl group, a c2_c3Q alkynyl group, a CVCw aryl group, a c7-C2 aralkylene group, c2_c2. The substituent of the heteroaryl group and the aralkyl group replaces at least one hydrogen atom of the alkyl group. Among the compounds represented by Formula 1, non-limiting examples of suitable unsubstituted crC3 oxime alkoxy groups used include methoxy groups, ethoxy groups, stearyl groups, cyclohexyl groups. Oxy group, naphthyloxy group, isopropyl 11 200846348

Voxy group, diphenoxy group and the like. At least one hydrogen atom of the alkoxy group may be substituted with a substituent selected from the above in connection with the κ3() group. In the compound represented by Formula 1, the appropriate unsubstituted

Non-limiting examples of the CrCw acid group include an ethyl fluorenyl group, an ethyl carbonyl group, an isopropyl group, a phenylcarbonyl group, a naphthylcarbonyl group, a diphenylcarbonyl group, a cyclohexylcarbonyl group, and the like. By. At least one hydrogen atom of the CVCw fluorenyl group may be substituted with a substituent selected from the above in connection with a thiol group. In the compound represented by Formula 1, non-limiting examples of suitable unsubstituted alkenyl groups to be used include compounds having a carbon-carbon double bond in the middle or at the end of the alkyl group defined above. For example, the unsubstituted q-c:3 nonenyl group may be selected from the group consisting of a vinyl group, a propylene group, a butene group, a hexenylene group, and the like. At least one hydrogen atom of the alkenyl group may be substituted with a substituent selected from the above in connection with the Ci_c3 alkyl group. _ In the compound represented by Formula 1, a non-limiting example of a suitable unsubstituted G-Csg alkynyl group used includes a carbon-carbon triple bond in the middle or at the end of the alkyl group defined above. compound of. For example, the unsubstituted Q-Cw alkynyl group may be selected from the group consisting of an ethynyl group, a propynyl group, a phenylethynyl group, a naphthylacetylene group, an isopropylethynyl group, a third-butylacetylene group. , a diphenylacetylene group and the like. At least one hydrogen 2 of the alkynyl group may be substituted with a substituent selected from the above in connection with the C1_CM alkyl group. 'In the compound of Formula 1, the unsubstituted 12 is used. Non-limiting examples of the aryl group include a c6-c3Q carbocyclic aromatic containing at least one aromatic ring. system. The at least one aromatic ring may include at least two rings fused to each other, or bonded to each other by a single bond, or the like. At least one hydrogen atom of the aryl group may be substituted with a substituent selected from the above in connection with the q-Cw alkyl group. The substituted or unsubstituted c6-c3Q aryl group may be selected from the group consisting of a phenyl fluorene, an alkylphenyl group (e.g., an ethylphenyl group), a CrCio alkyl diphenyl group (e.g., ethyl diphenyl). a group), a halophenyl group (eg, o-, m- and p-fluorophenyl groups and a dichlorophenyl group), a dicyanophenyl group, a trifluorophosphonium phenyl group , ortho-, meta- and p-nonylphenyl groups, o-, m- and p-anisyl groups, 2,4,6-trimethylphenyl groups, phenoxyphenyl groups, (α, Α-dimethylbenzyl)phenyl group, (Ν,Ν'-dimethyl)amine phenyl group, (Ν,Ν'_diphenyl)amine phenyl group, and cyclopentadienyl group a pentalenyl group, a fluorenyl fluorenyl group, a naphthyl group, a halophthyl group (eg, a fluoronaphthyl group), a CrC10 alkylnaphthyl group (eg, an anthranyl group), an alkoxynaphthyl group a group (eg, a methoxynaphthyl group), a fluorenyl group, a base group, a fluorenyl group, a terpene naphthalene group, a fluorenyl group, a fluorenyl group, a fluorenyl group, Mercapto group, phenanthryl group, triphenylene group, pyrenyl group, fast radical (chrys) Enyl) group, ethyl-fast group, sulfhydryl group, pherylenyl group, chlorpheniryl group, pentaphenyl group, pentacenyl group, a tetraphenylene group, a hexaphenyl group, a hexaphenyl group, a rubicenyl group, a coronenyl group, a dinaphthyl group, a heptaphenyl group, and Heptaphenyl group, pyranthrenyl group, ovalenyl group, and the like. 13 200846348 In the compounds represented by the formula, non-limiting examples of suitable unsubstituted heteroaryl groups used include at least one aromatic samarium comprising at least one selected from the group consisting of N, hydrazine, P and S Atom, in which the remaining ring members are carbon systems. The at least one aromatic ring may be at least two rings fused to each other, or bonded to each other by a single bond, or the like. At least one hydrogen atom of the heteroaryl group can be substituted with a substituent as discussed above in connection with the alkyl group. _ In the compound represented by Formula 1, non-limiting examples of suitable unsubstituted heteroaryl groups used include pyrazolyl groups, imidazolyl groups, azozolyl groups, thiazolyl groups , a triazolyl group, a tetrazolyl group, a bisazolyl group, a pyridyl group, a hydrazine group, a pyrimidinyl group, a triamminide group, a thiol group, a fluorene group a group, a quinolyl group, an isoquinolyl group, and the like. Non-limiting examples of substituents suitable as R] to R] of Formula 1 include a hydrogen atom, a Cl_Cl0 alkyl group, a Ci-C10 haloalkyl group, an alkenyl group, a C2_Cl() haloalkenyl group a group, a phenyl group, a halophenyl group, a Ci_Ci phenyl group, a crc10 alkoxyphenyl group, a naphthyl group, a halophthyl group, a Ci-Cw alkylnaphthyl group, and Ci-Ci decyloxynaphthyl group. Non-limiting examples of substituents suitable as L! and L2 of Formula 1 include a phenylene group, a phenyl group, a Ci_Ci 〇 alkyl phenyl group, a CrC10 alkoxy phenyl group, and a stretching group. A naphthyl group, a halo-naphthyl group, a crC1()alkyl-naphthyl group, and a Ci_CiQ alkoxy-naphthyl group. Non-limiting examples of substituents suitable as Ari and Ah of Formula 1 include a phenyl group, a halophenyl group, an alkylphenyl group, 14 200846348 alkoxyphenyl group, a naphthyl group, a halophthalene a group, an alkylnaphthyl group, a CrC10 alkoxynaphthyl group, an acridinyl group, a haridazinyl group, a Crc10 alkyl pyridyl group, a crc1() alkoxypyridyl group, a quinolyl group, a haloquinolyl group, an alkylquinolyl group, a CrCu alkoxyquininyl group, an isoquinolyl group, a succinylquinolyl group, a Crc10 alkyl group a salino group and an alkoxyisoquinolyl group. In a specific sad case, the formula la, lb, 1c and Id can be expressed as a compound having a molar ratio of pyridine.

Equation 1 b

15 200846348 lc

Id

10 In the formula la to Id, R3 to R12, A. And Ar2 are the same as described above for Formula 1. Non-limiting examples of compounds suitable for use as the imidazopyridine-based compound represented by Formula 1 include the following compounds 1 to 11. 16 200846348 % Compound 1 Compound 2

17 200846348 Compound 6

Compound 7 compound 8

Compound 9

Compound 10

18 200846348 Compound 11

The present compound of Formula 1 can be prepared by various methods. For example, by exemplifying the following, the compound represented by Formula 3 and the compound represented by Formula 3 and at least all of them are shown below, and the reaction of the compound represented by Formula I is obtained. Things. · The imidazole ratio is more than the bite-based formula 2

19 200846348 A bite-based compound that forms an organic luminescent body, for example, an organic light-emitting diode comprising a J-th layer. Between the first and second electrodes, the right-handed compound containing the second electrode of the second electrode and the second electrode is the organic layer of the mouth. . According to a specific state of the transport layer. There is a flaw in the ^ ^ stack layer can be electric 卞 曰 organic light-emitting diodes can also include white dry hole transport layer, electron blocking layer, light-emitting layer, hole resistance = injection = layer, electrical layer, electron injection layer And the layers of its combination. For example, when the second person, the pen transmission port, the mouth of the mouth is set to Φ + field 5 乂 type 1

The light-emitting diode can also be packaged with a special layer μ•, which is injected into the organic electron. + From the door transport layer, the light-emitting layer and the package of the king's eight layers. In addition, when the hair machine is formed from a sub-stone material, the first electrode may contain a hole resistance. ^ There are various other structures. 1 I light-emitting diode can be explained in Fig. 1. According to the present invention, an organic light-emitting diode having a surname of m6 m / and a body-like sample is explained. Structure. In Fig. 1, there is a first electrode/hole left layer/pen hole transmission layer/lighting Gongcheng smear layer/electron injection layer/second. ^ 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机 有机/ Structure of the electron injection layer / second electrode, or the structure of the first electrode / layer / hole transport layer / light-emitting layer / hole barrier layer / electron transport layer / electron injection layer / second electrode. The electron transport layer can be formed of a compound mainly composed of imiprazole represented by the formula i. According to an embodiment of the present invention, the light-emitting layer of the organic light-emitting diode Q ^ ^ , Kang, or white phosphorescent or fluorescent dopant. The phosphorescent dopant may be a cerium organometallic compound containing a compound selected from the group consisting of ^(1), Ti, &, 20 200846348

Metals of Hf, Eu, Tb, Tm, and combinations thereof. In the following, a method of fabricating an organic light-emitting diode according to a specific aspect of the present invention will be described with reference to an organic light-emitting device explained in Fig. i. Tian I first, by depositing or sputtering a material with a high work function on the substrate, forming a missing turtle pole can be an anode or a cathode. The substrate may be any substrate used in a conventional organic light-emitting device, and may be a glass substrate or a moon-permeable plastic substrate. It may be easy to handle, is waterproof, and has excellent mechanical strength, thermal stability, and transparency. And surface smoothness. The first electrode may be formed of ITO, IZO, Sn〇2, ZnO or any transparent material having high conductivity t. Next, a hole injection layer (HIL) may be formed on the first electrode by vacuum coating, spin coating, casting, Langmuir Blodgett (LB) deposition or the like. When the HIL is formed by vacuum coating, the vacuum coating conditions can be changed depending on the compound used to form the HIL, and the desired structure and thermal characteristics of the hil to be formed. However, usually the vacuum coating can be in the range of about 1 〇 0. 〇 to a coating temperature of about 50 (TC, ranging from about 1 〇 8 to about 10 Torr (mm), at a coating speed of from about 〇〇1 to about 100 Α / sec. Vacuum coating The thickness of the layer can range from about 10 Å to about 5 microns. When the HIL is formed by spin coating, the coating conditions can vary depending on the desired structure and thermal properties of the HIL to form the HIL to be formed. Typically, the coating speed can range from about 2 to about 5,000 rpm, and the temperature of the heat treatment (after the coating to remove the solvent) can range from about 80 to about 200. (: 21 200846348 The HIL material is not particularly limited, and may be any material known to form HILs. Non-limiting examples of suitable HIL materials include phthalocyanine compounds (such as copper phthalocyanine), star amine derivatives (such as TCTA (shown below) ), -MTDATA (shown below) and meta-MTDAPB), soluble and conductive polymers (such as polyaniline / dodecylbenzene sulfonic acid (Pani / DBSA), poly (3,4-ethylene II) Oxythiophene)/poly(4-styrenesulfonate) (PED OT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), (polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), and the like.

The thickness of the HIL can range from about 100 to about ΙΟ, ΟΟΟΑ. In a particular aspect, for example, the thickness can range from about 100 to about 1,000 Å. When the thickness of the HIL is within the above range, the HIL has excellent hole injecting ability, and an organic light-emitting diode having an excellent driving voltage can be obtained. A hole transport layer (HTL) can be formed on the HIL by vacuum coating, spin coating, casting, LB deposition or the like. When the HTL is formed by vacuum coating or spin coating, the conditions of coating and coating are similar to those for forming HIL, although the coating or coating conditions may vary depending on the material used to form the HTL. 22 200846348 〉 There are also special restrictions on HTL materials, and can be any HTL material known to be used as = (4) restrictive examples include 啼 衍 = = = N-phenyl scent and poly sputum scent , a typical amine derivative, having a tribute fused ring (eg, N, N, bis(3.tolyl)_n, n, _diphenylene diphenyl]: M,: diamine (TPD is shown below) And n, n, - bis (naphthalenediyl V-, phenylzydine (a-NpD shown below)), to be similar.

TPD

The thickness of a-NPD_~htl can range from about 5 〇 to about 1 _ person. In a specific sample, for example, when the thickness of the field HTL is in the above range in the range of from about (10) to about 6 GG A, the htl has excellent hole transporting ability, and an organic hair having an excellent driving voltage can be obtained. ^Dipole. An illuminating layer (EML) can be formed on the muscle by vacuum coating, spin coating, casting, LB deposition or the like. The conditions for forming the film and coating by vacuum coating or spin coating are similar to those for forming mL, although the bonding film and coating conditions may vary depending on the material used to form the EML. Various known luminescent materials can be formed to form a luminescent layer, and can include an existing host and a dopant. The dopant can be a known fluorescent dopant or a fluorene % photo dopant. Non-limiting examples of suitable host materials include A1Ch, 4,4'-team 1^dicarbazole-diphenyl (〇 ??), poly(positive_vinyl咔23 200846348 azole) (PVK), biphenyl Ethylene aryl (DS A), and the like. Non-limiting examples of suitable fluorescent dopants include IDE 102 and IDE 105 available from idemhsu Co. Non-limiting examples of suitable phosphorescent dopants include green phosphorescent dopants (e.g., lr(ppy)3 (ppy is an abbreviation for phenylhydrazine), (4,6_F2PPy)2Iii>iC, available from Covion, Ltd. TEB0〇2), red dish light dopant (such as octaethylporphyrin platinum (PtOEP)), the following 々 ★ "Shiyi 1 夂 5, the compound, Firpric, TBPe, and the like.

formula

Firpic

w One-W W repair agent, for 100 parts by weight, the dopant can be present in an amount of .... In one embodiment, the amount of substitution is about - about 12 parts by weight. When the dopant: 攸 is present in an amount of about 0 曰 5 parts, the wrinkle of the added dopant is increased, and the amount of 〇.丄 or the amount of the fluorescent dopant is less than about 20 dan: when the phosphorescence The concentration is quenched. π fruit shells can be prevented 24 200846348 EML thickness range can be from about 1 〇〇 to about. In a specific evil sample, for example, the thickness is in the range of from about 2 〇〇 to about 6 〇〇 a. When the thickness of the EML is within the above range, the EM]L has excellent light-emitting ability, and an organic light-emitting diode having an excellent driving voltage can be obtained. When the EML includes a phosphorescent dopant, a hole blocking layer (HBL) can be formed on the EML to prevent the triple excitons or holes from moving to the electron transport layer (ETL) (not shown in Figure 1). The hbl material is not particularly limited and may be any material known to form HBLs. Non-limiting examples of suitable hbl materials include dimethoprim derivatives, triazole derivatives, phenanthroline derivatives, Balq, BCP, and the like. The thickness of the HBL can range from about 50 to about 1, 〇0〇A. In a specific body, for example, the thickness is in the range of from about 1 〇〇 to about 3 〇〇 A. When the thickness of the S HBL is within the above range, the ruthenium has excellent hole blocking barrier force, and an organic light-emitting diode having an excellent driving voltage can be obtained. An electron transport layer (ETL) can be formed on the HBL by vacuum coating, spin coating, casting or the like. When the ETL is formed by vacuum coating or spin coating, the conditions of the coating and coating are generally similar to those for forming the HIL, although the coating or coating conditions may vary depending on the material used to form the crucible. The ETL can be formed of a compound mainly composed of imidazopyridine represented by Formula 1. ETL may also be formed from quinoline derivatives such as tris(8-quinolinic acid)aluminum (?ι^), taz or the like, which are known in the art. The thickness of the ETL can range from about 10 〇 to about 1, 〇〇〇Α. In a case of 25 200846348%, for example, when the thickness is in the range from about 100 to about 500 A, the thickness of the ETL is within the above range, the ETL has excellent fast transfer ability and can be obtained with excellent driving. Voltage organic light-emitting diodes. In addition, an electron injection layer (EIL) may be deposited on the ETL. EIL makes it easy to inject electrons from the cathode. The EIL may be formed of LiF, NaCl, CsF, Li20, BaO or the like, 4 materials being known in the art. The coating and coating of the muscles are similar to the conditions for forming the HIL, although they may be changed depending on the material used to form the EIL.

The thickness of the EIL can range from about i to about 1 person. In a specific embodiment, for example, when the thickness is in the range of from about 5 to about 9 Å, the EIL has an excellent electron injecting two to obtain an organic light-emitting diode having an excellent driving voltage. Finally, the first electrode can be formed on eil by vacuum coating, sputtering or the like. The second electrode can be used as a cathode or an anode. The second electrode may be formed of a metal, an alloy, a conductive compound of a work function, or a combination thereof. Non-limiting examples of materials suitable for the second electrode include, Mg, octa-Al-Li, Ca, Mg-In, Mg-Ag, and the like. Alternatively, a front surface light emitting diode can be produced using a transparent cathode formed of Tings or IZO. For the purpose of explanation only, it is not intended to limit the scope of the invention, and to provide a detailed description of the synthetic compounds! The following synthetic examples of 4, 7 and 7, in detail, the implementation of an organic light-emitting diode according to a specific aspect of the invention. 26 200846348 Synthesis Example 1: Synthesis of Compound i Synthesis of Compound 1 via Reaction Scheme 1 below : Reaction Process 1

27 200846348 Synthesis of intermediate 1 a 10 g of copper bromide (44 mmol) and 8 g of 2-amino hydrazine (35·8 mmol) were added to 250 ml of bromic acid and the mixture was heated To 65〇c. After the gas generation was stopped, the mixture was cooled to room temperature. The mixture was then added to 1000 ml of 2 〇 0 / 〇 aqueous hydrochloric acid and extracted with dichloromethane. The water remaining in the organic layer was removed using anhydrous MgS 4 and the resulting product was dried under pressure. The obtained product (dichloromethane: n-hexane = 4:1) was purified by column chromatography to afford 7.7 g of intermediate l (yield 75%). Synthesis of Intermediate lb 10 g of the intermediate la (34.8 mmol) was added to 100 ml of THF dehydrated under nitrogen pressure, and the temperature of the mixture was lowered to -78. Hey. 0. 5 Torr 2-naphthylmagnesium bromide (10 mmol) was slowly added to the mixture. The temperature of the mixture was increased to room temperature, and the mixture was stirred for 3 hours. An aqueous solution of ammonium chloride was added to the reacted mixture, and the resulting product was extracted with methylene chloride. The organic layer was dried using anhydrous MgS04 and the solvent was removed. The mixture obtained therefrom was dissolved with a small amount of diethyl ether. Then, petroleum ether was added to the mixture and stirred for several hours to obtain a solid compound. The obtained solid compound was filtered and dried in vacuo to obtain 176 g of dinaphthyl diol. 17 6 g of dinaphthyl diol (32·4 mmol) was dispersed in 200 ml of acetic acid under a nitrogen pressure. Then, 5.3 g of potassium iodide (330 mmol) and 58 g of sodium hypophosphite hydrate (660 mmol) were added to the mixture, and 28 200846348 was disturbed and refluxed for 3 hours. The obtained product was cooled to room temperature, filtered, washed with water and methanol, and then dried in vacuo to obtain η·3 g of pale yellow intermediate lb. Synthesis of intermediate lc 5 g of intermediate lb (9.81 mmol) was dissolved in 7 mL of THF dried under nitrogen pressure, and 4. 7 ml of butyl lithium 8 * Mo at -78 ° C Ear) added to the mixture. The mixture was stirred at the same temperature for several hours, and then 2.20 ml of trimethyl borate (29.4 mmol) was added to the mixture. The temperature of the mixture was increased to room temperature, and after 2 hours, 2N aqueous hydrochloric acid was added to the mixture, and the mixture was dropped for 3 hours. The obtained solid compound was filtered while being washed with a thief to obtain 32.7 g of pale yellow intermediate lc (yield 70%). Synthesis of Intermediate Id 3.39 g of 2-aminopyridine (35.98 mmol) and 1 g of 2,4,-dibromoethylbenzene (35.98 mmol) were dissolved in 15 mL of ethanol and refluxed. The mixture was 12 hours. The mixture was cooled to room temperature to give a white solid. • Rinse the resulting white solids with a saturated NaHC03 solution. The water remaining in the organic layer is removed by using anhydrous MgS〇4, dried under a reduced pressure, and then recrystallized (dichloromethane/n-hexane) to obtain an intermediate jd of 8·〇2 g, having a tablet Crystalline form (yield 82%). Synthesis of Compound 1 1.85 g of the intermediate lc (3.90 mmol) and 1 g of the intermediate (3.90 mmol) were added to a mixed solvent of 2.7 g of an aqueous potassium carbonate solution (19.5 mmol) and THF. 225 mg of Pd(PPh3)4 (19.5 mmol) was added to the mixture 29 200846348 while the mixture was stirred and the mixture was refluxed for 6 hours. The mixture was cooled to room temperature, and then the obtained solid compound was filtered, washed with water, ethanol and THF to obtain 1.73 g of Compound 1 as a pale yellow powder (yield: 71%). (mNMR (400MHz, CDCl3) 8.13-8.04 (7H), 8.〇1 (1Η), 7.97-7·92 (4Η), 7.86-7.82 (2H), 7.75 (2Η), 7·71 -7.58 (1〇Η), 7·32 (2Η), 7·15 (1Η), 6·75 (1Η)). Synthesis Example 2: Synthesis of Compound 4 Compound 4 was synthesized via Reaction Scheme 2 below: Reaction Scheme 2

Synthesis of Compound 4 Intermediate 4 d 5 g of the imidazopyridine compound Id (refer to Synthesis Example 1) (18.3 mmol) and 4.12 g of N-iodosuccinic acid (NIS) (18.3 mmol) were dissolved as a solvent. B guess. The mixture was allowed to stand at room temperature for 1 hour' and then 100 ml of chloroform was added to the compound 30 200846348. The mixture was washed with a 10% aqueous solution of sodium sulphate, washed with saturated aqueous sodium thiosulfate and water, and dried over anhydrous magnesium sulfate. The resulting product was then filtered and the solvent removed. The obtained solid was washed with methanol and filtered to obtain 5.8 g of an iodine compound (yield: 79%). The obtained iodine compound and 76.76 g of phenylboronic acid (145 mmol) were added to 1 g of potassium carbonate aqueous solution and In a mixed solvent of THF. To the mixture was added 335 mg of Pd(PPh3)4 while the mixture was stirred, and the mixture was refluxed for 24 hours. The resulting product was extracted with dichloromethane. The water remaining in the organic layer is removed using water-free MgS〇4 and dried under reduced pressure. The obtained product (ethyl acetate: n-hexane = 2:3) was purified by column chromatography to afford 2.93 g of intermediate 4d (yield 58%). Synthesis of Compound 4 Compound 4 was prepared in the same manner as Compound 丨 according to Synthesis Example 1, except that Intermediate 4 (1 was used instead of Intermediate id. 1 gram of intermediate 1 〇 (21·08 mmol) and 6.69 g of intermediate 4d (1916 mmol) was subjected to a Suzuki reaction, yielding 9.72 g of compound 4 in the form of a pale yellow powder (yield 73%). (1H NMR (400 MHz, CDC13) 8·〇8 (1Η) ),8·〇3-8·01(2η) 7·97-7·88(3Η), 7·81(1Η), 7.74-7.58 (12), 7·51々·40(1〇) 7· 29-7·23(3Η), 7·15(1Η), 6·69(1Η)). Synthesis Example 3: Synthesis of Compound 7 Compound 7 was synthesized via Reaction Scheme 3 below: 31 200846348

Reaction process 3

Compound 7 was prepared in the same manner as in Synthesis Example 1, except that Intermediate 7d was used instead of Intermediate Id. Substituting 1-aminoisoquinoline for 2-aminopyridine gave intermediate 7d. 10 g of intermediate lc (21.08 mb 32 200846348 mol) and 6.19 g of intermediate 7d (19.16 mmol) were subjected to a reaction of eucalyptus to give 9.03 g of compound 7 in the form of a pale yellow powder (yield 70%) ). (1H NMR (400MHz, CDC13) 8.69 (1Η), 8·12 (2Η), 8·07- 8·02 (5Η), 7·99·7.95 (4Η), 7.89-7.84 (2Η), 7.79 -7.75 (3Η), 7·71-7·65 (4Η), 7·64-7.54 (8Η), 7·33 (2Η), 7.02 (1Η)). Synthesis Example 4: Synthesis of Compound 3 Compound 3 was synthesized via Reaction Scheme 4 below. · Reaction Scheme 4

Compound 3 was prepared in the same manner as in Synthesis Example 1, except that Intermediate 3d was used instead of (iv) ld. The intermediate 3d was obtained by substituting 2,4, dibromopropionylbenzene for 2,4,-dioxaethylbenzene. 5 grams of intermediate ic (i 〇 54 mM) and 2.75 gram of intermediate 163d (9.58 _mol) were subjected to Suzuki reaction, yielding 4.15 g of compound 3 in the form of a pale yellow powder (yield 68%). (1H NMR (400MHz ^ CDC13) 8.12(2H), 8.〇7.8>〇2(5H), 7.97- 33 200846348 7.95(2H), 7.89-7.84(2H), 7.80-7.71(4H), 7.7〇 7.66(3H), 7.63-7.6G(7H), 7.32(2H), 7.15(1H), 6 83(m), 2 62(3H)). Synthesis Example 5: Synthesis of Compound 2 Compound 2 was synthesized via Reaction Scheme 5 below. · Reaction Scheme 5

Compound 2 was prepared in the same manner as in Synthesis Example 1, except that Intermediate 2e was used instead of Intermediates 113 and le. Intermediate 2c was obtained by using desertified phenylmagnesium instead of desertification 2_naphthyl. Make 5 grams of intermediate 2. (13% millimolar) and 3.32g intermediate ld (12.15 millimolar) were subjected to Suzuki reaction, and fragrantly produced (64 g of compound 2' was in the form of a pale yellow powder (yield 73%). (1 NMR (400 MHz, CDC13) 8.11 (1Η), 7.99 (2Η), 7.95 (1Η), 7·86 (1Η), 7·64 (1Η), 7·73-7·70 (2Η), 7.69 (1Η), 7.66 -7·61(7Η), 7·58(2Η), 7·56-7·50(4Η), 7·34(2Η), 7·17(1Η), 6.78(1Η)). Synthesis implementation Example 6: Synthesis of Compound 11 Compound 11 was synthesized via Reaction Scheme 6 below: 34 200846348 Reaction Scheme 6

Compound 11 was prepared in the same manner as in Synthesis Examples 5 and 4 using Intermediates 2c and 3d. 5 grams of intermediate 2c (13.36 millimoles) and 3.49 grams of intermediate 3d (12.15 millimoles) were subjected to Suzuki reaction, yielding 4.72 grams of compound hydrazine in the form of a pale yellow powder (yield 72%). (1H NMR (400MHz, CDC13) 7.97 (1Η), 7·91 (1Η), 7·85 (2Η), 7·80 (1Η), 7.73-7·70 (2Η), 7·69 (1Η) ), 7.66-7.61 (7Η), 7·58 (2Η), 7·56-7·50(4Η), 7·34(2Η), 7·19(1Η), 6.86(1Η), 2· 67(3Η)) 〇Example 1 Cut a 15 ohm/cm 2 (1200 Α) ΙΤΟ glass substrate into 5 〇 χ χ χ 50 宅 χ · 0·7 house size ' ' Ultrasonic isopropyl alcohol rinse $ cent雀里' then rinse with pure water for 5 minutes. The substrate was then rinsed with uv ozone for 30 minutes. An inter-MTDATA vacuum coating was applied to the substrate to form a hole injection layer having a thickness of 750 Å. Then, a-NpD vacuum coating was formed on the hole injection layer to form a hole transport layer having a thickness of 15 Å. A light-emitting layer having a thickness of 300 A was formed on the hole transport layer using 97% by weight of DSA as a host and 3% by weight of TBPe as a dopant. The compound 1 prepared by the synthesis example 1 was vacuum-coated on the light-emitting layer to form 35 200846348

An electron transport layer having a thickness of 2 Å.魃τι古 A ^ The L1F vacuum coating is formed on the electron transport layer to form an electronic immersion layer with a thick sound of 80 A, and then A1 vacuum coating is formed on the electron injection layer to form and the right war has 3000A. The thickness of the cathode completes the organic light-emitting diode. Example 2 An organic hair was produced in accordance with Example 1 except that the compound 4 prepared in Synthesis Example 2 was used as the material of the gas-polymerized layer. Example 3

An organic light-emitting diode was fabricated as in Example 1, except that the compound 7 prepared in Synthesis Example 3 was used as the material of the electron transport layer. Example 4 An organic light-emitting diode was fabricated according to the examples except that the compound 3 prepared in μ Example 4 was used as the material of the electron transport layer. Example 5 An organic light-emitting diode was fabricated as in Example 1, except that Compound 5 prepared in Synthesis Target 5 was used as a material of the electron transport layer. Example 6 An organic light-emitting diode was fabricated as in Example 1, except that the compound u prepared in Synthesis Example 6 was used as the material of the electron transport layer. Comparative Example An organic light-emitting diode was fabricated as in Example 1, except that Alq3 (8-hydroxyquinoline aluminum complex) was used as the material of the electron transport layer. Evaluation Example Current density (milliampere/square) of each organic light-emitting diode prepared according to Example 1 to J3 and Comparative Example was measured using PR650 (sPectr(R) Scan) Source Measurement Unit 36 200846348 (PhotoResearch Ltd) Eight points), drive voltage (volts), brightness (new candle / square meter) = high efficiency / watt). The results are shown in Table 1 below and Figures 2 and 3. Specifically, Fig. 2 is a graph showing voltage-current density characteristics of the organic light-emitting diode of Comparative Example 丨6 and the organic light-emitting diode of Comparative Example. Fig. 3 is a graph showing the degree of exemption-efficiency characteristics of the organic light-emitting diode of Comparative Example 1 (4) 6 and the organic light-emitting diode of Comparative Example. , Table 1

As shown in Table 1 and Figures 2 and 3, the organic light-emitting diodes of Examples 1 to 6 have improved current density, driving voltage, brightness, and efficiency as compared with the organic light-emitting diode of the comparative example. Therefore, an organic light-emitting diode having an organic layer of a compound mainly composed of the imidazolium represented by Formula 1 can be seen, which has a higher efficiency compared with the conventional organic light-emitting diode. Lower drive voltage and longer life. Capability II contains 1: an organic light-emitting diode m w of a compound having a high electron transport. The life of the organic layer of matter. Body, low drive voltage, high brightness, high efficiency and long

Although certain references have been made to this disclosure, those skilled in the art should understand that the scope and scope of the invention may be defined. The specific aspects of the nature explain and describe the various changes and modifications of the specific aspects described in this document, as illustrated by the following [simplified description of the drawings] by referring to the above detailed description, while taking into account the pictures of the appendix, The above and other features and advantages of the present invention will become more apparent, in which: Figure 1 is an illustration of an organic light-emitting diode according to a specific aspect of the present invention. 2 is a view comparing organic light-emitting diodes prepared according to Examples 2 to 6,

And a graph of voltage-current density characteristics of the organic light-emitting diodes prepared according to the comparative examples. Fig. 3 is a graph comparing the luminance-efficiency characteristics of the organic light-emitting diodes prepared according to the respective Examples 2 to 6, and the organic light-emitting diodes prepared according to the comparative examples. [Simple diagram description] None [Main component symbol description] None 38

Claims (1)

200846348, the scope of application for patents: 1 · A chemical compound consisting of imidazopyridine represented by the formula Wherein: respectively selected from a hydrogen atom::;,: I, R8, I, Rl °, Rl1 and 1^ substituted and unsubstituted C r 1 group, cyano group, oxy group Substituted and unsubstituted % unsubstituted Α·0^ fluorenyl group, c2-c3. a block group, a substituted group and an unsubstituted group, and a substituted or unsubstituted and unsubstituted #c6_c3() aryl group, a heteroaryl group; Groups, R5, R6 and R7 to small R9, R, p > ' have two rings forming a saturated or unsaturated; 10 rings of 11 and R. 12 τ at least two form saturated or unsaturated Ll and L2 is independently selected from an alkylene group, a substituted #草 bond, a substituted and unsubstituted substituted and unsubstituted and unsubstituted ^-(^❸ aryl group, and Ari and Ar eight a group consisting of heterocyclic aryl groups; 2 knives are selected from a group of substituted and unsubstituted CfCw aryl groups and unsubstituted K--(: Group of groups consisting of groups 39 200846348; P and q are respectively selected from integers from 1 to 5, and 'where m and η are both Hi and η are respectively selected from 〇 to 4 and the integer is not 0. The compound of claim 1 wherein R15 is selected from the group consisting of a hydrogen atom, a substituted and unsubstituted "complete group, substituted and unsubstituted C2_Ci" Alkenyl group, substituted and unsubstituted A C6-C12 aryl group and a group consisting of substituted and unsubstituted &c3_c"heteroaryl groups. 3. If you apply for a patent scope! a compound, wherein each is selected from the group consisting of a hydrogen atom alkyl group, a LA (tetra) group, a 12^ c10 alkenyl group, a C 2 -Ci fluorenyl group, a phenyl group, a dentate group, ^-C1G alkylphenyl group, hydrazine. An alkoxyphenyl group, a naphthyl group, a dentinyl group, a Ci-Cualkylnaphthyl group, and a Ci_Ci decylnaphthyl group. 4. A compound of claim i, wherein at least two of I to the core form a substituted or unsubstituted aromatic ring. 1 2 5 5. The compound of claim 1, wherein at least two of the 1 to & formations form a substituted or unsubstituted aromatic ring. A compound according to claim 1, wherein Li and L are each selected from a substituted and unsubstituted c"Ci2 extended aryl group and a substituted and unsubstituted heteroaryl group. 2. A group of compounds according to claim 1, wherein Li and L are each selected from the group consisting of a phenylene group, a (tetra)phenyl group, c "Ci. Azide extension = group, q- a group consisting of a Cw alkoxyphenylene group, a stretching naphthyl group, a N-naphthyl group 200846348 group, a crc1G alkyl-naphthyl group, and a c-CiG alkoxy-naphthyl group. A compound of claim i, wherein Ari and Αγ2 are each selected from the group consisting of a substituted and unsubstituted CrCu aryl group and a substituted and unsubstituted Cs-c12 heteroaryl group. 9. The compound of claim i, wherein VIII and VIII are each selected from the group consisting of a phenyl group, a halophenyl group, a Ci_Ci decyl phenyl group, a c10 alkoxyphenyl group, Naphthyl group, halophthyl group, c!_c(9)alkylnaphthyl group, q-Cn alkoxynaphthyl group, α-pyridyl group, halo.pyridyl group, qC B alkyl pyridyl group, Ci_Ci decyloxy pyridyl group, quinolyl group, orthoquinolyl group, Ci_Ci 〇 alkyl quinolinyl group, C1_C "alkoxyquinolinyl group a group consisting of a group, an isoquinolyl group, an _isoquinolyl group, a Cr C10 alkylisoquinolyl group, and a Ci_Ci{) alkoxyisoquinolyl group. 1) A compound of claim 1, wherein m is 0 and η is 1. U • A compound of the first paragraph of the patent application, in which both m and η are 1. 12. The imidazole pyridine-based compound according to the third aspect of the patent scope, wherein the imidazopyridine-based compound is selected from the group consisting of compounds represented by the formulas u, ib, b, and 1 d·· 200846348 42 200846348 Type Id 13. The compound of claim 1, wherein the oxime-based compound is selected from the group consisting of compounds 1 to 1 : Compound 1 Compound 2 43 200846348 Compound 5 Compound 6 Compound 7 compound 8 44 200846348 Compound 9 Compound 10 Compound 11 An organic light emitting diode (OLED) comprising: a first electrode; a second electrode; and an organic layer between the first and second electrodes, the organic layer comprising a compound as in claim 1 . 15. The organic light-emitting diode of claim 14, wherein the organic layer is an electron transport layer. 16. The organic light emitting diode according to claim 15 further comprising a group selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer and an electron injection layer. Layer. 45. The organic light-emitting diode of claim 14, further comprising a hole injection layer, a hole transport layer, a light-emitting layer and an electron injection layer, wherein the organic layer is an electron transport layer. 18. The organic light-emitting diode according to claim 14, wherein the imidazopyridine-based compound is selected from the group consisting of compounds represented by the formulas la, lb, lc, and Id: Compound 1a Compound lb Compound 1 c 46 200846348 Compound 1 d 19. The organic light-emitting diode according to claim 14, wherein the imidazopyridine-based compound is selected from the group consisting of compounds 1 to 11: Compound 1 Compound 2 47 200846348 Compound 5 Compound 7 Compound 8 48 200846348 Compound 9 Compound 10 XI. Schema: As the next page 49