JP6347922B2 - Compound having at least one of electron injection ability and electron transport ability, organic light emitting device, and flat panel display - Google Patents

Description

  The present invention relates to a compound having at least one of an electron injection ability and an electron transport ability, an organic light emitting device, and a flat panel display.

  An organic light emitting diode is a self-luminous element and has a wide viewing angle and excellent contrast. In addition, the organic light emitting device has the advantages that the response time is short, the luminance, the driving voltage, and the response speed characteristics are excellent, and that multiple colors are possible.

  A general organic light emitting device has a structure in which an anode is formed on a substrate, and a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially formed on the anode. Here, the hole transport layer, the light emitting layer, and the electron transport layer are organic thin films made of an organic compound.

  The driving principle of the organic light emitting device having the above-described structure is as follows.

  When a voltage is applied between the anode and the cathode, holes injected from the anode move to the light emitting layer through the hole transport layer, and electrons injected from the cathode pass through the electron transport layer. To move to the light emitting layer. The carriers such as holes and electrons recombine in the light emitting layer region to generate excitons. Light is generated when the exciton transitions from the excited state to the ground state.

Korean Published Patent No. 2008-0079095

  Here, an organic light emitting device using a conventional organic substance as an electron transport layer has a problem that a light emission life is short, and storage durability and reliability are low. Such problems arise from physical or chemical changes in the organic material, photochemical or electrochemical changes in the organic material, oxidation of the negative electrode, delamination, lack of durability, and the like.

  Accordingly, the present invention has been made in view of the above problems, and an object of the present invention is to provide a new and improved electron having more excellent electrical characteristics, higher charge transporting ability and light emitting ability. An object of the present invention is to provide a compound having at least one of an injection ability and an electron transport ability, an organic light emitting element, and a flat panel display.

In order to solve the above problems, according to one aspect of the present invention, there is provided a compound represented by the following chemical formula 1 and having at least one of an electron injection ability and an electron transport ability.
..Chemical formula 1

In Formula 1, each of R ₁ and R ₂ independently represents a halogen group, a cyano group, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, or Represents a substituted or unsubstituted C ₃ -C ₆₀ heteroaryl group, and R ₃ represents a substituted or unsubstituted C ₆ -C ₆₀ aryl group, or a substituted or unsubstituted C ₃ -C ₆₀ heteroaryl group. X represents a single bond or a substituted or unsubstituted C ₃ -C ₁₀ arylene group, A represents a substituted or unsubstituted C ₃ -C ₆₀ heteroaryl group, or a substituted or unsubstituted C _6. A condensed polycyclic group containing N, O or S which is —C ₆₀ is shown, and n is an integer of 1 to 7.

  In order to solve the above problem, according to another aspect of the present invention, the first electrode, the second electrode, and an organic layer interposed between the first electrode and the second electrode are provided. An organic light emitting device is provided, wherein the organic layer includes a compound having at least one of the electron injection ability and the electron transport ability.

  In order to solve the above-described problem, according to still another aspect of the present invention, the organic light-emitting device includes the organic light-emitting device, and the first electrode of the organic light-emitting device is electrically connected to the source electrode or drain electrode of the thin film transistor. A flat panel display device is provided.

  As described above, according to the present invention, a compound having at least one of a new and improved electron injection ability and electron transport ability, organic light emission, having superior electrical characteristics, higher charge transport ability and light emission ability. An element and a flat panel display are provided.

1 is a schematic view illustrating a structure of an organic light emitting device according to an embodiment of the present invention.

  Exemplary embodiments of the present invention will be described below in detail with reference to the accompanying drawings. In addition, in this specification and drawing, about the component which has the substantially same function structure, duplication description is abbreviate | omitted by attaching | subjecting the same code | symbol.

  The compound according to an embodiment of the present invention is represented by the following chemical formula 1.

..Chemical formula 1

In Formula 1, each of R ₁ and R ₂ independently represents a halogen group, a cyano group, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, or Represents a substituted or unsubstituted C ₃ -C ₆₀ heteroaryl group, and R ₃ represents a substituted or unsubstituted C ₆ -C ₆₀ aryl group, or a substituted or unsubstituted C ₃ -C ₆₀ heteroaryl group. X represents a single bond or a substituted or unsubstituted C ₃ -C ₁₀ arylene group, A represents a substituted or unsubstituted C ₃ -C ₆₀ heteroaryl group, or a substituted or unsubstituted C _6. A condensed polycyclic group containing N, O or S which is —C ₆₀ is shown, and n is an integer of 1 to 7.

  In the substituent A, at least one hydrogen of the unsubstituted heteroaryl group or the unsubstituted condensed polycyclic group containing N, O or S is a substituent described in the substituted alkyl group described later. Or a substituent in which at least one of a plurality of aryl groups and heteroaryl groups is linked by a single bond (for example, m-terphenyl group, 4,4 ′-(1,3-phenylene) It may be substituted with a dipyridine group (including, but not limited to, 4,4 ′-(1,3-phenylene) dipiridine group).

  The compound according to an embodiment of the present invention realizes an organic light emitting diode (OLED) with improved driving voltage and higher efficiency than existing electron injection materials and electron transport materials. In addition, according to such a compound, an organic light emitting device having an excellent driving life and improved power consumption due to an increase in power efficiency can be manufactured.

In the compound according to one embodiment of the present invention, in the structure of Chemical Formula 1, the substituent R ₃ is aligned with X in a straight line. Therefore, the compound has a long conjugation length, and thus a large dipole moment in the molecule. Here, a compound having an electron transporting ability or an electron injecting ability has a higher electron mobility as the dipole moment is larger. Therefore, the compound according to an embodiment of the present invention has a large intramolecular dipole moment and a high electron mobility, and thus can reduce the driving voltage of the organic light emitting device.

  The substituents in the compound of Formula 1 will be described more specifically.

  According to an embodiment of the present invention, in Formula 1, X is a single bond or phenylene.

According to another embodiment of the present invention, in Formula 1, R ₁ and R ₂ may be connected to form a spiro structure.

According to another embodiment of the present invention, in Formula 1, R ₁ and R ₂ may each independently be a methyl group, a phenyl group, or a pyridyl group.

According to another embodiment of the present invention, in Formula 1, R ₃ may be any one of Formulas 2a to 2f.

..Chemical formula 2a

..Chemical formula 2b

..Chemical formula 2c

..Chemical formula 2d

..Chemical formula 2e

..Chemical formula 2f

In the chemical formulas 2a to 2f, Y ₁ , Y ₂ and Y ₃ are each independently a linking group represented by —N═ or —C (R ₂₀ ) ═, and Z ₁ , Z ₂ and R 3 ₂₀ are each independently hydrogen, deuterium, substituted or unsubstituted _C 1 _{-C 20} alkyl group, a substituted or unsubstituted _C 6 _{-C 20} aryl group, a substituted or unsubstituted _C 3 _{-C 20} heteroaryl aryl group, a substituted or unsubstituted _C 6 _{-C 20} condensed Hajime _Tamaki, C 6 _{-C 20} aryl group or _C 3 _{-C 20} heteroaryl substituted amine group with a group, a halogen group, a cyano group, a nitro group, It is a hydroxyl group or a carboxylic acid group, p is an integer of 1 to 9, and * represents a bond.

  According to another embodiment of the present invention, in Formula 1, A may be any one of Formulas 3a to 3l.

..Chemical formula 3a

..Chemical formula 3b

..Chemical formula 3c

..Chemical formula 3d

..Chemical formula 3e

..Chemical formula 3f

..Chemical formula 3g

..Chemical formula 3h

..Chemical formula 3i

..Chemical formula 3j

..Chemical formula 3k

..Chemical formula 3l

In Formulas 3a to 3l, Y ₁ , Y ₂ and Y ₃ are each independently a linking group represented by —N═ or —C (R ₂₀ ) ═, and Z ₁ , Z ₂ , R ₂₀ , R ₃₀ and R ₃₁ are each independently hydrogen, deuterium, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted C 1 ₃ -C ₂₀ heteroaryl group, a substituted or unsubstituted _C 6 _{-C 20} condensed Hajime Tamaki, a halogen group, a cyano group, a nitro group, a hydroxyl group or a carboxylic acid group, _{Q 1} is S or O , P is an integer of 1 to 7, and * indicates a bond.

  Among the substituents used in the present specification, the definitions of typical substituents are as follows (note that the number of carbon atoms of the substituents limited below is exemplary, It does not limit the properties of the group).

_C 1 _{-C 60} alkyl group unsubstituted, for example, a linear or branched, Representative examples include methyl group, ethyl group, propyl group, isobutyl group, sec- butyl group, a pentyl group, iso -An amyl group, a hexyl group, a heptyl group, an octyl group, a nonanyl group, a dodecyl group, etc. can be mentioned. One or more hydrogens in the alkyl group are deuterium, halogen, hydroxyl group, nitro group, cyano group, amino group, amidino group, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or a salt _thereof, C 1 _{-C 10} alkyl _group, C 1 _{-C 10} alkoxy _group, C 2 _{-C 10} alkenyl _group, C 2 _{-C 10} alkynyl _group, C 6 _{-C 16} aryl group or _{C 4,} it may be substituted with -C ₁₆ heteroaryl group.

C ₂ -C ₆₀ alkenyl group unsubstituted, at least one carbon to middle and top ends of the unsubstituted alkyl group - meaning that it contains carbon double bonds. Representative examples include ethenyl group, propenyl group, butenyl group and the like. At least one hydrogen in the alkenyl group may be substituted with the substituent described in the above-mentioned substituted alkyl group.

C ₂ -C ₆₀ alkynyl group unsubstituted, at least one carbon to middle and top ends of the unsubstituted alkyl group - meaning that it contains carbon triple bond. Typical examples include acetylene group, propylene group, phenylacetylene group, naphthylacetylene group, isopropylacetylene group, t-butylacetylene group, diphenylacetylene group and the like. At least one hydrogen in the alkynyl group may be substituted with the substituent described in the above-mentioned substituted alkyl group.

_C 3 _{-C 60} cycloalkyl group unsubstituted _means C 3 _{-C 60} cyclic alkyl groups. At least one hydrogen in the cycloalkyl group may be substituted with the substituent described in the above-mentioned substituted alkyl group.

The C ₁ -C ₆₀ unsubstituted alkoxy group is a functional group having a structure of —OA (where A is, for example, the aforementioned unsubstituted C ₁ -C ₆₀ alkyl group). Examples thereof include a methoxy group, an ethoxy group, a propoxy group, an isopropyloxy group, a butoxy group, and a pentoxy group. At least one hydrogen in the alkoxy group may be substituted with the substituent described in the above-mentioned substituted alkyl group.

C ₆ -C ₆₀ aryl group unsubstituted means a carbocyclic aromatic system functional group containing one or more aromatic rings. When the aryl group has two or more rings, they may be linked to each other through a fused or single bond. The term aryl includes aromatic functional groups such as phenyl, naphthyl, anthracenyl. In addition, one or more hydrogens in the aryl group may be substituted with the substituents described for the substituted alkyl group.

Examples of substituted or unsubstituted _C 6 _{-C 60} aryl group, a phenyl _group, C 1 _{-C 10} alkylphenyl group (for example, ethylphenyl group), a halophenyl group (e.g., o-, m- and p- fluoro phenyl group, dichlorophenyl group), a cyanophenyl group, dicyanophenyl group, a trifluoromethoxyphenyl group, a biphenyl group, a halobiphenyl group, a cyanobiphenyl _groups, C 1 _{-C 10} alkyl biphenyl _group, C 1 _{-C 10} alkoxynaphthyl biphenyl group, o-, m- and p-tolyl groups, o-, m- and p-cumenyl groups, mesityl groups, phenoxyphenyl groups, (α, α-dimethylbenzene) phenyl groups, (N, N′-dimethyl) aminophenyl Group, (N, N′-diphenyl) aminophenyl group, pentarenyl group, indenyl group, naphthyl group, halo Fuchiru groups (e.g., fluoronaphthyl _groups), C 1 _{-C 10} alkyl naphthyl groups (e.g., methylnaphthyl _groups), C 1 _{-C 10} alkoxynaphthyl group (for example, methoxynaphthyl group), a cyanonaphthyl group, an anthracenyl group, an azulenyl Group, heptalenyl group, acenaphthylenyl group, phenalenyl group, fluorenyl group, anthraquinolyl group, methylanthryl group, phenanthryl group, triphenylene group, pyrenyl group, chrysenyl group, ethyl-chrysenyl group, picenyl group, perylenyl group, chloroperenyl group, pentaphenyl Group, pentacenyl group, tetraphenylenyl group, hexaphenyl group, hexacenyl group, rubicenyl group, coronyl group, trinaphthylenyl group, heptaphenyl group, heptacenyl group, pyrantrenyl group, obalenyl group, etc. It can gel.

The unsubstituted C ₃ -C ₆₀ heteroaryl group contains one or more aromatic rings, and the atoms constituting the aromatic ring are 1, 2 or 3 selected from N, O, P or S These are functional groups containing heteroatoms. When the heteroaryl group has two or more rings, they may be connected to each other through a single bond or the like. Examples of unsubstituted C ₄ -C ₆₀ heteroaryl groups include pyrazolyl, imidazolyl, oxazolyl, thiazolyl, triazolyl, tetrazolyl, oxadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, triazinyl, carbazolyl Group, indolyl group, quinolinyl group, isoquinolinyl group, dibenzothiophene group and the like. Further, at least one hydrogen in the heteroaryl group may be substituted with the substituent described in the above-mentioned substituted alkyl group.

An unsubstituted C ₆ -C ₆₀ aryloxy group is a functional group represented by —OA ₁ , and A ₁ is the C ₆ -C ₆₀ aryl group. Examples of the aryloxy group include a phenoxy group. At least one hydrogen in the aryloxy group may be substituted with the substituent described in the above-mentioned substituted alkyl group.

_C 6 _{-C 60} arylthio group unsubstituted is a functional group represented by -SA _{1, A 1} is the _C 6 _{-C 60} aryl group. Examples of the arylthio group include a benzenethio group and a naphthylthio group. Among the arylthio groups, at least one or more hydrogens may be substituted with the substituents described above for the substituent of the substituted alkyl group.

An unsubstituted C ₆ -C ₆₀ condensed polycyclic group is a substituent containing two or more rings in which one or more aromatic rings and one or more non-aromatic rings are fused to each other, or in the ring The substituent which has an unsaturated group which does not have a conjugated structure is shown. The condensed polycyclic group is distinguished from the aforementioned aryl group or heteroaryl group in that it has no aromaticity as a whole functional group.

  The condensed polycyclic group containing N, O or S includes N, O or S, and includes two or more rings in which one or more aromatic rings and one or more non-aromatic rings are fused to each other. A substituent or a substituent having an unsaturated group having no conjugated structure in the ring is shown. The condensed polycyclic group containing N, O or S means a functional group that cannot have aromaticity as a whole functional group.

  One or more hydrogens of the condensed polycyclic group or the condensed polycyclic group containing N, O, or S may be substituted with the substituents described for the substituted alkyl group.

  Specific examples of the compound represented by Chemical Formula 1 according to the embodiment of the present invention include the following compounds 1 to 70. However, the present invention is not limited to these.

  An organic light emitting device according to another embodiment of the present invention is an organic light emitting device including a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode. The organic layer includes a compound represented by Formula 1.

  The organic layer includes a hole injection layer, a hole transport layer, a functional layer having a hole injection capability and a hole transport capability at the same time (hereinafter also referred to as “H-functional layer”), a buffer layer , An electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a functional layer having both electron transport ability and electron injection ability (hereinafter referred to as “E-functional layer”) At least one layer may be included.

  More specifically, the organic layer may be an electron injection layer, an electron transport layer, or an E-functional layer. In particular, the organic layer may be an electron transport layer.

  According to an embodiment of the present invention, the organic light emitting device includes an electron injection layer, an electron transport layer, an E-functional layer, a light emitting layer, a hole injection layer, a hole transport layer, or an H-functional layer. In addition, the electron injection layer, the electron transport layer, or the E-functional layer includes a compound having at least one of the electron injection ability and the electron transport ability according to the embodiment of the present invention. Furthermore, the light emitting layer may include an anthracene compound, an arylamine compound, or a styryl compound.

  According to another embodiment of the present invention, the organic light emitting device includes an electron injection layer, an electron transport layer, a light emitting layer, a hole injection layer, a hole transport layer, or an H-functional layer. In addition, any one of the red layer, the green layer, the blue layer, and the white layer of the light emitting layer contains a phosphorescent compound, and the hole injection layer, the hole transport layer, or the H-functional layer has a charge. A product may be included. The charge generation material may be a p-dopant, and the p-dopant may be, for example, a quinone derivative, a metal oxide, or a cyano group-containing compound.

  According to still another embodiment of the present invention, the organic layer may include an electron transport layer, and the electron transport layer may include an electron transporting organic compound and a metal complex. The metal complex may be a Li complex.

  In the present specification, the “organic layer” is a term indicating a single layer or a plurality of layers interposed between the first electrode and the second electrode in the organic light emitting device.

  FIG. 1 is a schematic cross-sectional view of an organic light emitting device according to an embodiment of the present invention. Hereinafter, with reference to FIG. 1, the structure and manufacturing method of the organic light emitting device according to the embodiment of the present invention will be described.

  Here, as a substrate (not shown), a substrate used in a general organic light emitting device can be used. In particular, a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling and waterproofness can be used.

The first electrode is formed on the substrate by providing a first electrode material using a vapor deposition method or a sputtering method. When the first electrode is an anode, a material having a large work function is selected as the first electrode material so that hole injection is easy. The first electrode may be a reflective electrode or a transmissive electrode. As the first electrode material, for example, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), etc. that are transparent and have excellent conductivity are used. Can do. Alternatively, magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or the like can be used. It is also possible to form one electrode as a reflective electrode.

  The first electrode may have a single layer or two or more multilayer structures. . The first electrode may have, for example, a three-layer structure of ITO / Ag / ITO, but the present invention is not limited to this.

  An organic layer is provided on the first electrode.

  The organic layer may include a hole injection layer, a hole transport layer, a buffer layer (not shown), a light emitting layer, an electron transport layer, an electron injection layer, or the like.

  The hole injection layer (HIL) can be formed on the first electrode using various methods such as a vacuum deposition method, a spin coating method, a casting method, and an LB (Langmuir-Blodgett) method.

When the hole injection layer is formed by the vacuum deposition method, the deposition conditions are, for example, a deposition temperature of about 100 to about 500 ° C., and a degree of vacuum of about 10 ⁻⁸ to about 10 ⁻³ torr (about 1.3 × 10 6 ⁻⁶ to about 1.3 × 10 ⁻¹ Pa), and the deposition rate is selected in the range of about 0.01 to about 100 Å / sec (about 0.001 to about 10 nm / sec). However, the deposition conditions are not limited to the above because they vary depending on the compound used as the material of the hole injection layer, the structure of the target hole injection layer, the thermal characteristics, and the like.

  When the hole injection layer is formed by the spin coating method, the coating conditions are, for example, a coating speed of about 2,000 rpm to about 5,000 rpm, and a heat treatment temperature for solvent removal after coating of about 80 ° C. to 200 ° C. Selected by temperature range. However, the coating conditions are not limited to the above because they vary depending on the compound used as the material of the hole injection layer, the structure of the target hole injection layer, and the thermal characteristics.

  A known hole injection material can be used as the hole injection material. Known hole injection materials include, for example, N, N′-diphenyl-N, N′-bis- [4- (phenyl-m-tolyl-amino) -phenyl] -biphenyl-4,4′-diamine ( DNTPD), phthalocyanine compounds such as copper phthalocyanine, 4,4 ′, 4 ″ -tris (3-methylphenylphenylamino) triphenylamine (m-MTDATA), N, N′-di (1-naphthyl) -N, N′-diphenylbenzidine (NPB), 4,4 ′, 4 ″ -tris {N, Ndiphenylamino} triphenylamine (TDATA), 4,4 ′, 4 ″ -tris (N, N-2-naphthylphenyl) Amino) triphenylamine (2-TNATA), polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly (3,4-ethylenedioxythiop) ) / Poly (4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), or polyaniline / poly (4-styrenesulfonate) (PANI / PSS). However, the present invention is not limited to these.

  The thickness of the hole injection layer is, for example, about 100 mm to about 10,000 mm (about 10 nm to about 1,000 nm), more specifically about 100 mm to about 1,000 mm (about 10 nm to about 100 nm). May be. When the thickness of the hole injection layer is included in the above range, desired hole injection characteristics can be obtained without substantially increasing the driving voltage.

  Next, a hole transport layer (HTL) is formed on the hole injection layer using various methods such as vacuum deposition, spin coating, casting, and LB. In the case of forming a hole transport layer by a vacuum deposition method and a spin coating method, the deposition conditions and the coating conditions are generally selected from the same condition range as that for forming the hole injection layer. However, the vapor deposition conditions and the coating conditions are not limited to the above because they differ depending on the compounds used.

  A known hole transport material can be used as the hole transport material. Known hole transport materials include, for example, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N, N′-bis (3-methylphenyl) -N, N′-diphenyl- [1,1-biphenyl]. -4,4'-diamine (TPD), 4,4 ', 4 "-tris (N-carbazolyl) triphenylamine (TCTA), N, N'-di (1-naphthyl) -N, N'-diphenyl Although benzidine (NPB) etc. can be mentioned, this invention is not limited to these.

  The hole transport layer may have a thickness of, for example, about 50 to about 2,000 (about 5 nm to about 200 nm), more specifically, about 100 to about 1,500 (about 10 to 150 nm). Good. When the thickness of the hole transport layer is included in the above range, desired hole transport characteristics can be obtained without substantially increasing the drive voltage.

  The H-functional layer (functional layer having both hole injecting ability and hole transporting ability) includes at least one of the hole injecting layer material and the hole transporting layer material as described above. Further, the thickness of the H-functional layer is, for example, about 500 mm to about 10,000 mm (about 50 nm to about 1,000 nm), more specifically about 100 mm to about 1,000 mm (about 10 nm to about 100 nm). It may be. When the thickness of the H-functional layer is included in the above-described range, desired hole injection and hole transport characteristics can be obtained without substantially increasing the driving voltage.

  Here, at least one of the hole injection layer, the hole transport layer, and the H-functional layer includes at least one of a compound represented by the following chemical formula 300 and a compound represented by the following chemical formula 350. But you can.

..Chemical formula 300

..Chemical formula 350

In Formulas 300 and 350, Ar ₁₁ , Ar ₁₂ , Ar _21, and Ar ₂₂ are each independently a substituted or unsubstituted C ₅ -C ₆₀ arylene group.

  In Formula 300, e and f are each independently an integer of 0 to 5, for example, 0, 1 or 2. More specifically, e is 1 and f is 0, but the present invention is not limited thereto.

In the chemical formulas 300 and 350, for example, R _{51 to} R ₅₈ , R _{61 to} R ₆₉ , and R ₇₁ and R ₇₂ are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted _C 2 _{-C 60} alkynyl group, a substituted or unsubstituted _C 1 _{-C 60} alkoxy group, a substituted or unsubstituted _C 3 _{-C 60} cycloalkyl group, a substituted or unsubstituted substituted _C 5 _{-C 60} aryl group, a substituted or unsubstituted _C 5 _{-C 60} aryloxy group or a substituted or unsubstituted _C 5 -C, _It may be a ₆₀ arylthio group. More specifically, R _{51 to} R ₅₈ , R _{61 to} R ₆₉ , and R ₇₁ and R ₇₂ are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₁₀ alkyl group (e.g., methyl group, ethyl group, propyl group, butyl group, a pentyl group, and hexyl _group), C 1 _{-C 10} alkoxy group (e.g., methoxy group, an ethoxy group, a propoxy group, a butoxy group, etc. pentoxy group), or, deuterium, halogen, hydroxyl group, a cyano group Nitro group, amino group, amidino group, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, and C ₁ -C ₁₀ alkyl group and C ₁ -C ₁₀ alkoxy group, phenyl group, naphthyl group, anthryl group, fluorenyl group, pyrenyl group, or deuterium substituted with one or more of acid groups or salts thereof , halogen, hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₁₀ alkyl group And a C ₁ -C ₁₀ alkoxy group substituted with one or more of a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, and a pyrenyl group, the present invention is not limited thereto. Absent.

In the chemical formula 300, R ₅₉ represents phenyl group, naphthyl group, anthryl group, biphenyl group, pyridyl group, deuterium, halogen, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, Among carboxylic acid groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid groups or salts thereof, substituted or unsubstituted C ₁ -C ₂₀ alkyl groups, and substituted or unsubstituted C ₁ -C ₂₀ alkoxy groups It is one of phenyl group, naphthyl group, anthryl group, biphenyl group and pyridyl group substituted with one or more.

  According to an embodiment of the present invention, the compound represented by the chemical formula 300 may be a compound represented by the following chemical formula 300A. However, the present invention is not limited to this.

..Chemical formula 300A

For the detailed description of R ₅₁ , R ₆₁ , R ₆₂ and R ₅₉ in the chemical formula 300A, refer to the above description.

  For example, at least one of the hole injection layer, the hole transport layer, and the H-functional layer may include one or more of the following compounds 301 to 320, but is not limited thereto.

  At least one of the hole injection layer, the hole transport layer, and the H-functional layer has the aforementioned known hole injection material, known hole transport material, and hole injection ability and hole transport ability at the same time. In addition to the compound having, a charge generating substance may be further included in order to improve the conductivity of the film.

  The charge generating material may be a p-dopant, for example. The p-dopant is one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but the present invention is not limited to these. For example, typical examples of the p-dopant include tetracyanoquinone dimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethane (F4-TCNQ). Quinone derivatives, metal oxides such as tungsten oxide and molybdenum oxide, and cyano group-containing compounds such as the following compound 200. However, the present invention is not limited to them.

..F4-TCNQ

..Compound 200

  When the hole injection layer, the hole transport layer, or the H-functional layer further includes the charge generation material, the charge generation material may be a hole injection layer, the hole transport layer, or the H-functional layer. It may be homogenously distributed within or non-uniformly distributed, and various variations are possible.

  A buffer layer is formed between at least one of the hole injection layer, the hole transport layer, and the H-functional layer and the light emitting layer. The buffer layer can compensate for the optical resonance distance by the wavelength of the light emitted from the light emitting layer and improve the efficiency. Here, the buffer layer may include a known hole injection material and hole transport material. In addition, the buffer layer may include the same material as one of materials included in the hole injection layer, the hole transport layer, and the H-functional layer formed below the buffer layer.

  Further, the light emitting layer (EML) is formed on the hole transport layer, the H-functional layer, or the buffer layer by using a method such as a vacuum deposition method, a spin coating method, a cast method, or an LB method. Here, when the light emitting layer is formed by the vacuum vapor deposition method and the spin coating method, the vapor deposition conditions and the coating conditions are generally selected from the almost same condition range as in the formation of the hole injection layer. However, the vapor deposition conditions and the coating conditions are not limited to the above because they differ depending on the compounds used.

  The light emitting layer may include a host.

  Examples of the host include Alq3 (tris (8-quinolinolato) aluminum), 4,4′-N, N′-dicavazole-biphenyl (CBP), poly (n-vinylcarbazole) (PVK), 9,10- Di (naphthalen-2-yl) anthracene (DNA), 4,4 ′, 4 ″ -tris (N-carbazolyl) triphenylamine (TCTA), 1,3,5-tris (N-phenylbenzimidazole-2- Yl) benzene (TPBI), 3-tert-butyl-9,10-di (naphth-2-yl) anthracene (TBADN), E3, distyrylarylene (DSA), 4,4′-bis (9-carbazole) -2,2'-dimethyl-biphenyl (dmCBP), the following compounds 501 to 509, and the like can be used. The present invention is not limited to.

  Alternatively, an anthracene-based compound represented by the following chemical formula 400 can be used as the host.

..Chemical formula 400

In Formula 400, Ar ₁₁₁ and Ar ₁₁₂ are each independently a substituted or unsubstituted C ₅ -C ₆₀ arylene group, and Ar _{113 to} Ar ₁₁₆ are each independently substituted or unsubstituted. A C ₁ -C ₁₀ alkyl group, or a substituted or unsubstituted C ₅ -C ₆₀ aryl group, and g, h, i and j are each independently an integer of 0 to 4.

For example, in Formula 400, Ar ₁₁₁ and Ar ₁₁₂ are a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group, or a phenylene group substituted with one or more of a phenyl group, a naphthyl group, and an anthryl group. , A naphthylene group, a phenanthrenylene group, a fluorenyl group, or a pyrenylene group, but the present invention is not limited thereto.

  Further, for example, in the chemical formula 400, g, h, i, and j may be 0, 1, or 2 independently.

Further, for example, in Formula 400, Ar _{113 to} Ar ₁₁₆ are each independently a C ₁ -C ₁₀ alkyl group, phenyl group, or naphthyl substituted with one or more of a phenyl group, a naphthyl group, and an anthryl group. Group, anthryl group, pyrenyl group, phenanthrenyl group, fluorenyl group, or deuterium, halogen, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group Or a salt thereof, a phosphate group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a phenyl group, a naphthyl group, an anthryl Substituted with one or more of a group, a pyrenyl group, a phenanthrenyl group and a fluorenyl group. Phenyl group, naphthyl group, anthryl group, pyrenyl group, phenanthrenyl group and a fluorenyl group, and is one of the following chemical formula 600, the present invention is not limited thereto.

..Chemical formula 600

  For example, the anthracene compound represented by Formula 400 is one of the following compounds, but the present invention is not limited thereto.

  Alternatively, an anthracene compound represented by the following chemical formula 401 can be used as the host.

..Chemical formula 401

For the detailed description of Ar _{122 to} Ar ₁₂₅ in the chemical formula 401, refer to the description related to Ar ₁₁₃ in the chemical formula 400.

In Formula 401, Ar ₁₂₆ and Ar ₁₂₇ are each independently a C ₁ -C ₁₀ alkyl group (eg, a methyl group, an ethyl group, or a propyl group).

  In Formula 401, k and l are each independently an integer of 0 to 4. For example, the k and l are 0, 1 or 2.

  For example, the anthracene compound represented by the chemical formula 401 is one of the following compounds, but the present invention is not limited thereto.

  When the organic light emitting device is a full color organic light emitting device, the light emitting layer is patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer.

  Here, at least one of the red light emitting layer, the green light emitting layer, and the blue light emitting layer may include the following dopant (ppy = phenylpyridine).

  For example, the following compounds can be used as the red dopant, but the present invention is not limited to these.

  For example, the following compounds can be used as the green dopant, but the present invention is not limited to these.

  On the other hand, the dopant contained in the light emitting layer may be a Pd complex or a Pt complex as described later, but the present invention is not limited thereto.

  Moreover, although the Os complex mentioned later may be sufficient as the dopant contained in the said light emitting layer, this invention is not limited to these.

  When the light emitting layer includes a host and a dopant, the dopant content is generally selected in the range of about 0.01 to about 15 parts by weight, based on about 100 parts by weight of the host. However, the present invention is not limited to this.

  The light emitting layer has a thickness of, for example, about 100 to about 1,000 (about 10 to about 100 nm), more specifically about 200 to about 600 (about 20 to about 60 nm). When the thickness of the light emitting layer is included in the above range, excellent light emission characteristics can be obtained without substantially increasing the driving voltage.

  Next, an electron transport layer (ETL) is formed on the light emitting layer by various methods such as vacuum deposition, spin coating, and casting. In the case of forming an electron transport layer by a vacuum deposition method and a spin coating method, the deposition conditions or coating conditions are generally selected from substantially the same condition range as that for forming the hole injection layer. However, the vapor deposition conditions and the coating conditions are not limited to the above because they differ depending on the compounds used.

  The electron transport layer functions to stably transport electrons injected from the electron injection electrode (cathode). Therefore, as the material of the electron transport layer, the compound according to the embodiment of the present invention or a known electron transport material can be used. Examples of known electron transport materials include Alq3 (tris (8-quinolinolato) aluminum), aluminum (III) bis (2-methyl-8-hydroxyquinoline) -4-phenylphenolate (BAlq), beryllium bis (benzo Quinoline derivatives such as quinoline-10-olate) (Bebq2), 1,2,4-triazole derivatives (TAZ), 9,10-di (naphthalen-2-yl) anthracene (DNA), compound 201, and compound 202 Materials can be used. However, the present invention is not limited to these.

..Chemical formula 201

..Chemical formula 202

  The thickness of the electron transport layer is, for example, about 100 to about 1,000 (about 10 to about 100 nm), and more specifically about 150 to about 500 (about 15 to about 50 nm). When the thickness of the electron transport layer is included in the above range, desired electron transport characteristics can be obtained without substantially increasing the driving voltage.

  The electron transport layer may further contain a metal-containing substance in addition to a known electron transport organic compound.

  The metal-containing material may be, for example, a Li complex. Representative examples of the Li complex include 8-hydroxyquinolinolatolithium (Liq), the following compound 203, and the like.

..Chemical formula 203

  Further, an electron injection layer (EIL) having a function of facilitating injection of electrons from the negative electrode is laminated on the electron transport layer. As the material for the electron transport layer, the compound according to the embodiment of the present invention can be used, but the material is not particularly limited.

As the material for forming the electron injection layer, for example, a known substance such as LiF, NaCl, CsF, Li ₂ O, BaO or the like can be arbitrarily used. Generally, the deposition conditions of the electron injection layer are selected from the same condition range as in the formation of the hole injection layer. However, the vapor deposition conditions are not limited to the above because they vary depending on the compounds used.

  The thickness of the electron injection layer is, for example, about 1 to about 100 (about 0.1 to about 10 nm), more specifically about 3 to about 90 (about 0.3 to about 9 nm). When the thickness of the electron injection layer is included in the above range, desired electron injection characteristics can be obtained without substantially increasing the drive voltage.

  A second electrode is provided on the organic layer. The second electrode is a cathode that is an electron injection electrode. The second electrode may be formed using a metal, an alloy, an electrically conductive compound, and a mixture thereof having a small work function. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg). -Ag) or the like can be formed into a thin film to form the second electrode as a transmissive electrode. On the other hand, when obtaining a front light emitting element, the second electrode may be formed as a transmissive electrode using ITO or IZO, and various modifications are possible.

  As mentioned above, although the said organic light emitting element was demonstrated with reference to FIG. 1, this invention is not limited to the said illustration.

  When a phosphorescent dopant is used for the light emitting layer, in order to prevent a phenomenon in which triplet excitons or holes diffuse into the electron transport layer, or between the electron transport layer and the light emitting layer, or E- A hole blocking layer (HBL) may be formed between the functional layer and the light emitting layer. The hole blocking layer (HBL) can be formed using a method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. Here, when the hole blocking layer is formed by the vacuum vapor deposition method and the spin coating method, the vapor deposition condition or the coating condition is generally selected from the almost same condition range as in the formation of the hole injection layer. However, the vapor deposition conditions or the coating conditions are not limited to the above because they vary depending on the compounds used. In addition, as a material of the hole blocking layer (HBL), known hole blocking materials can be used, and typical examples include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and the like. Can do. For example, the following 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) can be used as the hole blocking layer material.

  The hole blocking layer has a thickness of, for example, about 20 to about 1,000 (about 2 nm to about 100 nm), more specifically about 30 to about 300 (about 3 to about 30 nm). When the thickness of the hole blocking layer satisfies the above range, excellent hole blocking characteristics can be obtained without substantially increasing the driving voltage.

  The organic light emitting device according to the present invention may be provided in various types of flat panel display devices such as passive matrix organic light emitting display devices and active matrix organic light emitting display devices. In particular, when provided in an active matrix organic light emitting display device, the first electrode formed on the substrate side is electrically connected as a pixel electrode to a source electrode or a drain electrode of a thin film transistor. The organic light emitting device according to the present invention may be provided in a flat panel display device capable of displaying a screen on both sides, for example.

  In addition, the organic layer of the organic light emitting device according to the embodiment of the present invention is formed by a vapor deposition method using the compound according to the embodiment of the present invention or a wet method of coating the compound according to the embodiment of the present invention in a solution. May be.

  Hereinafter, although the organic light emitting element which concerns on embodiment of this invention is given more concretely, giving a synthesis example and an Example, this invention is not limited to the following synthesis example and Example.

Synthesis Example 1: Synthesis of Compound 5

Synthesis of Intermediate I-1 4.80 g (20 mmol) of 4H-cyclopenta [def] phenanthrene (Compound A) was added to 20 mL of dimethyl sulfoxide (DMSO) and 20 mL of 50% aqueous sodium hydroxide solution, and then 2.96 g of iodomethane. (21 mmol) was added slowly. After reacting at room temperature for 24 hours, extraction was performed 3 times with 50 ml of water and 50 ml of diethyl ether. The collected organic layer was dried over magnesium sulfate and the solvent was evaporated. The obtained residue was separated and purified by silica gel column chromatography to obtain 3.70 g of Intermediate I-1 (yield 85%). The produced compound was confirmed by MS / FAB (mass spectroscopy / fast atom bombardment).
C ₁₇ H ₁₄ : calculated value 218.10, actually measured value 218.32

Synthesis of Intermediate I-2 Intermediate I-1 3.70 g (17.0 mmol), 10% palladium charcoal 600 mg was dissolved in methanol / methylene chloride (volume ratio 1/1) mixed solution 100 ml, and then hydrogen pressure was applied. (60 psi (about 41.4 MPa)) and stirred for 15 hours. After filtering to remove the catalyst, the solvent was evaporated. The obtained residue was separated and purified by silica gel column chromatography to obtain 3.52 g of intermediate I-2 (yield 94%). The compound produced was confirmed by MS / FAB.
C ₁₇ H ₁₆ : calculated value 220.12, actually measured value 220.33

Synthesis of intermediate I-3 20 g of CuBr ₂ was dissolved in 60 mL of distilled water, and 40 g of neutral alumina was added to the aqueous solution at room temperature. After evaporation of the solvent, the resulting residue was placed at 100 ° C. and 4 Torr (about 533 Pa) pressure for 15 hours to obtain CuBr ₂ absorbed in alumina. After dissolving 4.40 g (7.00 mmol) of Intermediate I-2 in 140 mL of carbon tetrachloride, 62 g of CuBr ₂ absorbed in the above-mentioned alumina was added at room temperature. The solid filtered after stirring for 12 hours at 60 ° C. was washed with 60 mL of carbon tetrachloride. The obtained residue was separated and purified by silica gel column chromatography to obtain 2.14 g of intermediate I-3 (yield 81%). The compound produced was confirmed by MS / FAB.
C ₁₇ H ₁₄ Br _2: Calculated 375.94, Found 376.11

Was dissolved Intermediate I-4 of the synthetic intermediates I-3 2.14 g of (5.66 mmol) in _CS 2 70 mL, 3 hours slowly added dropwise bromine 0.32mL the (6.22 mmol) was dissolved in CS ₂ To do. After stirring for 1 hour, it was concentrated in vacuo. The obtained residue was separated and purified by silica gel column chromatography to obtain 1.92 g of Intermediate I-4 (yield 90%). The compound produced was confirmed by MS / FAB.
C ₁₇ H ₁₂ Br _2: Calculated 373.93, Found 374.14

Synthesis of Intermediate I-5 Intermediate I-4 1.92 g (5.09 mmol), phenylboronic acid (Compound B) 0.34 g (2.99 mmol), tetrakis (triphenylphosphine) palladium (0) (Pd ( PPh ₃ ) ₄ ) 0.29 g (0.25 mmol) and K ₂ CO ₃ 0.62 g (4.48 mmol) were dissolved in 60 ml of a mixed solution of tetrahydrofuran (THF) / H ₂ O (volume ratio 2/1). , And stirred at 70 ° C. for 5 hours. The reaction solution was cooled to room temperature, 40 ml of water was added, and the mixture was extracted 3 times with 50 ml of ethyl ether. The collected organic layer was dried over magnesium sulfate and the solvent was evaporated. The obtained residue was separated and purified by silica gel column chromatography to obtain 0.82 g of Intermediate I-5 (yield 74%). The compound produced was confirmed by MS / FAB.
C ₂₃ H ₁₇ Br: Calculated value 372.05, measured value 372.19

Synthesis of Intermediate I-6 Intermediate I-5 3.72 g (10.0 mmol), bis (pinacolato) diborane 2.54 g (10.0 mmol), [1,1′-bis ( Diphenylphosphino) ferrocene] dichloropalladium (II) ([1,1′-bis (diphenylphosphino) ferrocene) dichloropalladium (II) (hereinafter referred to as PdCl ₂ (dppf) ₂ ) 0.36 g (0.5 mmol) and KOAc 2.94 g (30.0 mmol) was dissolved in 40 ml of DMSO and stirred for 6 hours at 80 ° C. The reaction solution was cooled to room temperature and extracted three times with 50 ml of water and 50 ml of diethyl ether. The layer is dried over magnesium sulfate and the solvent is Was emitted. The resulting residue was separated and purified by silica gel column chromatography to give Intermediate I-6 3.48g (80% yield). The generated compound was identified by MS / FAB.
C ₂₉ H ₂₉ BO ₂ : Calculated value 420.22, measured value 420.45

Synthesis intermediate I-6 of compound 5 0.92 g (2.20 mmol), 2- (4-bromophenyl) -1-phenyl-1-benzimidazole 0.69 g (compound C) (2.20 mmol), tetrakis ( Triphenylphospin) palladium (Pd (PPh ₃ ) ₄ ) 0.127 g (0.11 mmol) and K ₂ CO ₃ 0.45 g (3.3 mmol) were mixed in THF / H ₂ O (volume ratio 2/1). After dissolving in 40 ml of solution, the mixture was stirred at 70 ° C. for 5 hours. The reaction solution was cooled to room temperature, 30 ml of water was added, and the mixture was extracted 3 times with 30 ml of ethyl ether. The collected organic layers were dried over magnesium sulfate and the solvent was evaporated. The obtained residue was separated and purified by silica gel column chromatography to obtain 50.94 g (yield 76%) of a compound. The compound produced was confirmed by MS / FAB.
C ₄₂ H ₃₀ N _2: calc 562.24, found 563.33

Synthesis Example 2: Synthesis of Compound 14

Synthesis of Intermediate I-7 2.68 g (10 mmol) of 2-chloro-4,6-diphenyl- [1,3,5] -triazine, 2.82 g (10.0 mmol) of 4-bromo-phenylboronic acid, Pd (PPh ₃ ) ₄ 0.58 g (0.5 mmol) and K ₂ CO ₃ 4.14 g (30.0 mmol) were dissolved in 60 ml of a THF / H ₂ O (volume ratio 2/1) mixed solution, and then 70 ° C. For 5 hours. The reaction solution was cooled to room temperature and extracted three times with 60 mL of water and 60 mL of diethyl ether. The collected organic layers were dried over magnesium sulfate and the solvent was evaporated. The obtained residue was separated and purified by silica gel column chromatography to obtain 2.56 g of Intermediate I-6 (yield 66%). The compound produced was confirmed by MS / FAB.
C ₂₂ H ₁₈ BrN ₃ : calculated value 403.06, actually measured value 403.22.

Synthesis of Intermediate I-8 Intermediate I-8 was obtained in the same manner as the synthesis of Intermediate I-5, except that 4-pyridineboronic acid was used instead of phenylboronic acid. The compound produced was confirmed by MS / FAB.
C ₂₂ H ₁₆ BrN: calculated value 373.04, actual value 373.16

Synthesis of Intermediate I-9 In the same manner as the synthesis of Intermediate I-6, Intermediate I-8 was used instead of Intermediate I-5, to give Intermediate I-9. The compound produced was confirmed by MS / FAB.
C ₂₈ H ₂₈ BNO _2: Calculated 421.22, Found 421.41

Synthesis of Compound 14 In the same manner as the synthesis of Compound 5, instead of Intermediate I-6, Intermediate I-9 was replaced with 2- (4-bromophenyl) -1-phenyl-1-benzimidazole. Compound 14 was obtained using Intermediate I-7. The compound produced was confirmed by MS / FAB.
C ₄₄ H ₃₄ N _4: Calculated 618.27, Found 619.36

Synthesis Example 3: Synthesis of Compound 32

Synthesis of Intermediate I-10 Intermediate I-10 was obtained in the same manner as the synthesis of Intermediate I-5, using 6-quinolineboronic acid instead of phenylboronic acid. The compound produced was confirmed by MS / FAB.
C ₂₆ H ₁₈ BrN: calculated value 423.06, actual value 423.23

Synthesis of Intermediate I-11 Intermediate I-11 was obtained in the same manner as the synthesis of Intermediate I-6, except that Intermediate I-10 was used instead of Intermediate I-5. The compound produced was confirmed by MS / FAB.
C ₃₂ H ₃₀ BNO ₂ : calculated value 471.23, actually measured value 471.41

Synthesis of Intermediate I-12 3,5-diphenyl- [1,2,4] -triazole 2.21 g (10 mmol), 1-bromo-4-iodobenzene 4.24 g (15.0 mmol), CuI 0.10 g (0.5 mmol), 18-crown-6-ether 0.13 (0.5 mmol) and K ₂ CO ₃ 4.14 g (30.0 mmol) were added to 1,3-dimethyl-3,4,5,6- After dissolving in 50 mL of tetrahydro-2 (1H) -pyrimidinone (DMPU), the mixture was stirred at 170 ° C. for 24 hours. The reaction solution was cooled to room temperature and extracted three times with 60 mL of water and 60 mL of dichloromethane. The collected organic layers were dried over magnesium sulfate and the solvent was evaporated. The obtained residue was separated and purified by silica gel column chromatography to obtain 2.56 g of Intermediate I-12 (yield 68%). The compound produced was confirmed by MS / FAB.
C ₂₀ H ₁₄ BrN ₃ : calculated value 375.03, actually measured value 375.16

Synthesis of Compound 32 In the same manner as the synthesis of Compound 5, instead of Intermediate I-6, Intermediate I-11 was replaced with 2- (4-bromophenyl) -1-phenyl-1-benzimidazole. Compound 32 was obtained using Intermediate I-12. The compound produced was confirmed by MS / FAB.
C ₄₆ H ₃₂ N _4: Calculated 613.25, Found 614.36

Synthesis Example 4: Synthesis of Compound 45

Synthesis of Intermediate I-13 Intermediate I-13 was obtained in the same manner as the synthesis of Intermediate I-5, using 2-phenanthreneboronic acid instead of phenylboronic acid. The compound produced was confirmed by MS / FAB.
C ₃₁ H ₂₁ Br: Calculated value 472.08, measured value 472.23

Synthesis of Intermediate I-14 Intermediate I-14 was obtained in the same manner as the synthesis of Intermediate I-6, except that Intermediate I-13 was used instead of Intermediate I-5. The compound produced was confirmed by MS / FAB.
C ₃₇ H ₃₃ BO ₂ : calculated value 520.25, measured value 520.36

Synthesis of Intermediate I-15 In the same manner as the synthesis of Intermediate I-5, instead of Intermediate I-4, 2,6-dibromopyridine was replaced with 4-bromo-phenylboronic acid instead of 4- Intermediate 1-15 was obtained using pyridineboronic acid. The compound produced was confirmed by MS / FAB.
C ₁₀ H ₇ BrN _2: Calculated 233.97, Found 234.06

Synthesis of Compound 45 In the same manner as the synthesis of Compound 5, instead of Intermediate I-6, Intermediate I-14 was replaced with 2- (4-bromophenyl) -1-phenyl-1-benzimidazole. Intermediate 45 was obtained using intermediate I-15. The compound produced was confirmed by MS / FAB.
C ₄₁ H ₂₈ N ₂ : calculated value 624.25, actual value 625.39

Synthesis Example 5 Synthesis of Compound 55

Synthesis of Intermediate I-16 In the same manner as the synthesis of Intermediate I-5, instead of phenylboronic acid, 2- (9,10-phenanthroline) -boronic acid was used to obtain Intermediate I-16. Got. The compound produced was confirmed by MS / FAB.
C ₂₉ H ₁₉ BrN ₂ : calculated value 257.97, actually measured value 258.03

Synthesis of Intermediate I-17 Intermediate I-17 was obtained in the same manner as the synthesis of Intermediate I-6, except that Intermediate I-16 was used instead of Intermediate I-5. The compound produced was confirmed by MS / FAB.
C ₃₅ H ₃₁ BN ₂ O ₂ : calculated value 522.24, measured value 522.38

Synthesis of Intermediate I-18 Intermediate I-18 was obtained in the same manner as the synthesis of Intermediate I-5, but using 2-bromo-benzothiazole instead of Intermediate I-4. The compound produced was confirmed by MS / FAB.
C ₁₃ H ₈ BrNS: calculated value 288.95, actual value 289.21

Synthesis of Compound 55 In the same manner as the synthesis of Compound 5, instead of Intermediate I-6, Intermediate I-17 was replaced with 2- (4-Bromophenyl) -1-phenyl-1-benzimidazole. Intermediate 55 was obtained using Intermediate I-18. The compound produced was confirmed by MS / FAB.
C ₄₂ H ₂₇ N ₃ S: Calculated 625.23, Found 626.34

Synthesis Example 6 Synthesis of Compound 60

Synthesis of Intermediate I-19 Intermediate I-19 was obtained in the same manner as the synthesis of Intermediate I-5, except that 4-cyanophenylboronic acid was used instead of phenylboronic acid. The compound produced was confirmed by MS / FAB.
C ₃₄ H ₂₀ BrN: calculated value 522.43, actual value 522.65

Synthesis of Intermediate I-20 Intermediate I-20 was obtained in the same manner as the synthesis of Intermediate I-6, except that Intermediate I-19 was used instead of Intermediate I-5. The compound produced was confirmed by MS / FAB.
C ₄₀ H ₃₂ BNO ₂ : calculated value 569.25, actually measured value 569.42.

Synthesis of Intermediate I-21 In the same manner as the synthesis of Intermediate I-5, using 2-bromo-imidazo [1,2-a] pyrazine instead of Intermediate I-4, Intermediate I- 21 was obtained. The compound produced was confirmed by MS / FAB.
C ₁₂ H ₈ BrN ₃ : calculated value 272.99, measured value 273.31

Synthesis of Compound 60 In the same manner as the synthesis of Compound 5, instead of Intermediate I-6, Intermediate I-20 was replaced with 2- (4-Bromophenyl) -1-phenyl-1-benzimidazole. Compound 60 was obtained using Intermediate I-21. The compound produced was confirmed by MS / FAB.
C ₄₆ H ₂₈ N ₄ : calculated value 605.19, actually measured value 606.30

  The following compounds were additionally synthesized using the synthesis method of the synthesis route and appropriate raw materials. In Tables 1 to 5, 1H NMR (nuclear magnetic resonance) and MS / FAB of the synthesized compounds are shown.

  Other compounds in Tables 1 to 5 can be easily recognized by those skilled in the art by referring to the aforementioned synthesis route and raw material.

Example 1
The anode used was a Corning 15 Ω / cm ² (1,200 mm (120 nm)) ITO glass substrate cut to a size of 50 mm × 50 mm × 0.7 mm. The glass substrate was ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes each, then irradiated with ultraviolet rays for 30 minutes, and further exposed to ozone for cleaning. Then, this glass substrate was provided in the vacuum evaporation apparatus.

  First, 4,4 ′, 4 ″ -tris (N, N-2-naphthylphenylamino) triphenylamine (2-TNATA), which is a known material, is vacuum deposited on the substrate as a hole injection layer. Next, as a hole transporting compound, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB), which is a known substance, was used as a hole transporting compound. A hole transport layer was formed by vacuum deposition to a thickness of 300 mm (30 nm).

  On the hole transport layer, 9,10-di (naphthalen-2-yl) anthracene (DNA), which is a known compound as a blue fluorescent host, is a known compound, 4,4 as a blue fluorescent dopant. '-Bis (2,2-diphenylvinyl) -1,1'-biphenyl (DPVBi) was co-evaporated at a mass ratio of 98: 2 to form a light emitting layer with a thickness of 300 mm (30 m).

  Next, the compound 5 of the present invention was deposited as an electron transport layer on the light emitting layer to a thickness of 300 mm (30 nm). Furthermore, LiF, which is an alkali metal halide, is deposited on the electron transport layer as an electron injection layer to a thickness of 10 mm (1 nm), and Al is vacuum deposited to a thickness of 3,000 mm (300 nm) (negative electrode). An organic light emitting device was manufactured by forming a LiF / Al electrode.

This element had a current density of 50 mA / cm ² , a driving voltage of 5.25 V, and an emission luminance of 2,050 cd / m ² . The luminous efficiency was 4.10 cd / A, and the half life (hr @ 100 mA / cm ² ) was 291 hours.

Example 2
An organic light emitting device was manufactured in the same manner as in Example 1 except that the compound 14 was used instead of the compound 5 when forming the electron transport layer.

This device had a current density of 50 mA / cm ² , a driving voltage of 5.31 V, and an emission luminance of 2,355 cd / m ² . The light emission efficiency was 4.71 cd / A, and the half life (hr @ 100 mA / cm ² ) was 257 hours.

Example 3
An organic light emitting device was fabricated in the same manner as in Example 1 except that the compound 32 was used instead of the compound 5 when forming the electron transport layer.

This element had a current density of 50 mA / cm ² , a driving voltage of 5.42 V, and an emission luminance of 2,240 cd / m ² . The luminous efficiency was 4.48 cd / A, and the half-life (hr @ 100 mA / cm ² ) was 245 hours.

Example 4
An organic light emitting device was manufactured in the same manner as in Example 1 except that the compound 45 was used instead of the compound 5 when forming the electron transport layer.

This device had a current density of 50 mA / cm ² , a driving voltage of 5.20 V, and an emission luminance of 2,258 cd / m ² . The light emission efficiency was 4.51 cd / A, and the half life (hr @ 100 mA / cm ² ) was 283 hours.

Example 5
An organic light emitting device was fabricated in the same manner as in Example 1 except that the compound 55 was used instead of the compound 5 when forming the electron transport layer.

This device had a current density of 50 mA / cm ² , a driving voltage of 5.49 V, and an emission luminance of 2,140 cd / m ² . The luminous efficiency was 4.28 cd / A, and the half life (hr @ 100 mA / cm ² ) was 203 hours.

Example 6
An organic light emitting device was manufactured in the same manner as in Example 1 except that the compound 60 was used instead of the compound 5 when forming the electron transport layer.

This device had a current density of 50 mA / cm ² , a driving voltage of 5.44 V, and an emission luminance of 2,211 cd / m ² . The light emission efficiency was 4.42 cd / A, and the half life (hr @ 100 mA / cm ² ) was 234 hours.

Comparative Example 1
An organic light emitting device was fabricated in the same manner as in Example 1 except that Alq3, which is a known substance, was used instead of the compound 5 when forming the electron transport layer.

This element had a current density of 50 mA / cm ² , a driving voltage of 7.85 V, and an emission luminance of 1,560 cd / m ² . The luminous efficiency was 3.12 cd / A, and the half-life (hr @ 100 mA / cm ² ) was 113 hours.

Comparative Example 2
An organic light emitting device was fabricated in the same manner as in Example 1 except that Chemical Formula 700, which is a known substance, was used instead of Compound 5 when forming the electron transport layer.

This element had a current density of 50 mA / cm ² , a driving voltage of 6.05 V, and an emission luminance of 1,960 cd / m ² . The luminous efficiency was 3.92 cd / A, and the half life (hr @ 100 mA / cm ² ) was 201 hours.

..Chemical formula 700

  Table 6 summarizes the device characteristics and life results of each example.

  Referring to Table 6, the organic light emitting device using the compound having the structure of Chemical Formula 1 according to the present invention as an electron transporting material has a driving voltage of about 1 V compared to the case where Alq3 or Chemical Formula 700, which is a known substance, is used. It can be seen that the efficiency is improved and the IV characteristics are excellent. In particular, the organic light emitting device using the compound having the structure of Formula 1 according to the present invention as an electron transporting material is found to have a significantly improved lifetime when Examples 1 to 6 and Comparative Examples 1 and 2 are compared.

  As described above, the compound for an organic light emitting device according to the embodiment of the present invention has excellent electrical characteristics, high charge transporting ability and light emitting ability. Therefore, by using the compound for an organic light emitting device according to the embodiment of the present invention, the light emission efficiency and the device life are good, the color coordinates are appropriate, and high efficiency, low voltage, high luminance, and long life are obtained. An organic light emitting device can be fabricated.

  In addition, the compound for an organic light emitting device according to the embodiment of the present invention has a high glass transition temperature and can prevent crystallization, and can be used for fluorescent devices and phosphorescent devices of all colors such as red, green, blue, and white. It can be used as a suitable electron transport material, and can also be used as a green, blue, or white light emitting material.

  The preferred embodiments of the present invention have been described in detail above with reference to the accompanying drawings, but the present invention is not limited to such examples. It is obvious that a person having ordinary knowledge in the technical field to which the present invention pertains can come up with various changes or modifications within the scope of the technical idea described in the claims. Of course, it is understood that these also belong to the technical scope of the present invention.

The compound having at least one of the electron injection ability and the electron transport ability of the present invention and the organic light emitting device containing the compound can be effectively applied to, for example, a display-related technical field.

Claims (19)

A compound represented by the following chemical formula 1 and having at least one of an electron injection ability and an electron transport ability.
Here, in the chemical formula 1,
R ₁ and R ₂ are each independently a halogen group, a cyano group, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, or a substituted or unsubstituted group. shows the C ₃ -C ₆₀ heteroaryl group,
R ₃ represents a substituted or unsubstituted C ₆ -C ₆₀ aryl group, or a substituted or unsubstituted C ₃ -C ₆₀ heteroaryl group,
X represents a single bond or a substituted or unsubstituted C ₃ -C ₁₀ arylene group;
A represents a substituted or unsubstituted _C 3 _{-C 60} heteroaryl group or a substituted or unsubstituted a _C 6 _{-C 60} in N, condensed polycyclic group containing O or S,,
n is it indicates an integer of 1-7,
In Formula 1, R ₃ is any one of Formulas 2a to 2f .

Here, in the chemical formulas 2a to 2f,
Y ₁ , Y ₂ and Y ₃ are each independently a linking group represented by —N═ or —C (R ₂₀ ) ═ ,
Z ₁ , Z ₂ and R ₂₀ are each independently hydrogen, deuterium, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₆ -C ₂₀ aryl group, substituted or unsubstituted _C 3 _{-C 20} heteroaryl group, a substituted or unsubstituted _C 6 _{-C 20} condensed Hajime _Tamaki, C 6 _{-C 20} aryl group or _C 3 _{-C 20} heteroaryl substituted amine group with a group, halogen group , A cyano group, a nitro group, a hydroxyl group or a carboxylic acid group,
p is an integer of 1 to 9,
* Indicates binding.   The compound having at least one of an electron injection ability and an electron transport ability according to claim 1, wherein X is a single bond or phenylene. _{3. The} compound having at least one of an electron injection ability and an electron transport ability according to claim 1, wherein in Formula 1, R ₁ and R ₂ are linked to form a spiro structure. _{3. The} compound having at least one of an electron injection ability and an electron transport ability according to claim 1, wherein R ₁ and R ₂ in Formula 1 are each independently a methyl group, a phenyl group, or a pyridyl group. The compound which has at least one of the electron injection ability and the electron transport ability according to any one of claims 1 to 4, wherein A is any one of Chemical Formulas 3a to 3l.

Here, in the chemical formulas 3a to 3l,
Y ₁ , Y ₂ and Y ₃ are each independently a linking group represented by —N═ or —C (R ₂₀ ) ═,
Z ₁ , Z ₂ , R ₂₀ , R ₃₀ and R ₃₁ are each independently hydrogen, deuterium, substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₆ -C ₂₀ aryl. group, a substituted or unsubstituted _C 3 _{-C 20} heteroaryl group, a substituted or unsubstituted _C 6 _{-C 20} condensed Hajime Tamaki, a halogen group, a cyano group, a nitro group, a hydroxyl group or a carboxylic acid group,
Q ₁ is S or O;
p is an integer of 1 to 7,
* Indicates binding. The compound having at least one of the electron injection ability and the electron transport ability according to any one of claims 1 to 5 , wherein the compound of the chemical formula 1 is any one of the following compounds.
A first electrode;
A second electrode;
An organic light emitting device comprising an organic layer interposed between the first electrode and the second electrode,
The said organic layer is an organic light emitting element containing the compound which has at least one of the electron injection ability and electron transport ability as described in any one of Claims 1-6 . The organic light-emitting device according to claim 7 , wherein the organic layer includes an electron injection layer, an electron transport layer, or a functional layer having both electron injection ability and electron transport ability. The organic light-emitting device according to claim 7 , wherein the organic layer is an electron transport layer. The organic layer includes a light emitting layer, an electron injection layer, an electron transport layer, or a functional layer having both electron injection ability and electron transport ability,
The electron injection layer, the electron transport layer, or the functional layer having the electron injection ability and the electron transport ability at the same time includes a compound having at least one of the electron injection ability and the electron transport ability,
The organic light emitting device according to claim 7 , wherein the light emitting layer includes an anthracene compound, an arylamine compound, or a styryl compound. The organic layer includes a light emitting layer, a hole injection layer, a hole transport layer, or a functional layer having a hole injection capability and a hole transport capability at the same time,
The organic light emitting device according to claim 7 , wherein any one of the red layer, the green layer, the blue layer, and the white layer of the light emitting layer includes a phosphorescent compound. The organic light emitting device according to claim 11 , wherein the hole injection layer, the hole transport layer, or the functional layer having the hole injection ability and the hole transport ability at the same time includes a charge generation material. The organic light emitting device of claim 12 , wherein the charge generation material is a p-dopant. The organic light-emitting device according to claim 13 , wherein the p-dopant is a quinone derivative, a metal oxide, or a cyano group-containing compound. The organic light emitting device according to claim 7 , wherein the organic layer includes an electron transport layer, and the electron transport layer includes an electron transporting organic compound and a metal complex. The organic light emitting device according to claim 15 , wherein the metal complex is a Li complex. The organic light emitting device according to claim 15 or 16 , wherein the metal complex is LiQ or the following compound 203.
The said organic layer is formed in a wet process using the compound which has at least one of the electron injection ability and electron transport ability as described in any one of Claims 1-6. The organic light emitting device according to item. A flat panel display comprising the organic light emitting device according to any one of claims 7 to 18 , wherein the first electrode of the organic light emitting device is electrically connected to a source electrode or a drain electrode of a thin film transistor.