KR102269130B1 - Organic light emitting device - Google Patents

Abstract

a first electrode; a second electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes a compound of Formula 1 or a compound of Formula 2;
For the description of Chemical Formulas 1 and 2, refer to the detailed description of the invention.

Description

Organic light emitting device

It relates to an organic light emitting device.

An organic light emitting diode (OLED) is a self-luminous device that has a wide viewing angle and excellent contrast, has a fast response time, has excellent luminance, driving voltage and response speed characteristics, and can be multicolored.

A typical organic light emitting device may have 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 diode 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 emission layer via the hole transport layer, and electrons injected from the cathode move to the emission layer via the electron transport layer. Carriers such as holes and electrons recombine in the emission layer region to generate excitons. Light is generated as this exciton changes from an excited state to a ground state.

There is a continuing need for a material that has excellent electrical stability, high charge transport ability or light emitting ability, has a high glass transition temperature and can prevent crystallization compared to conventional organic monomolecular materials.

To provide an organic light emitting device characterized by high color purity, high efficiency, and long lifespan.

According to one aspect of the present invention, a first electrode; a second electrode; and an organic layer interposed between the first electrode and the second electrode,

An organic light emitting device is provided, wherein the organic layer includes a compound of Formula 1 or a compound of Formula 2:

<Formula 1>

<Formula 2>

In Formula 1 and Formula 2,

R ₁ , R ₂ , R ₂₁ and R ₂₂ are each independently deuterium, a substituted or unsubstituted C 1 to C 60 alkyl group, a substituted or unsubstituted C 3 to C 60 cycloalkyl group, a substituted or unsubstituted C 6 to C 6 an aryl group of 60, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted condensed polycyclic group having 6 to 30 carbon atoms, a fluorine group, -CF ₃ or a cyano group;

R ₃ to R ₁₂ and R ₂₃ to R ₃₄ are each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C 1 to C 60 alkyl group, a substituted or unsubstituted C 2 to C 60 alkenyl group, substituted or an unsubstituted C 3 to C 60 cycloalkyl group, a substituted or unsubstituted C 3 to C 60 cycloalkenyl group, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted C 3 to C 60 cyclo an alkenyl group, a substituted or unsubstituted C 3 to C 60 heteroaryl group, or a substituted or unsubstituted C 6 to C 30 condensed polycyclic group.

According to another aspect of the present invention, there is provided a flat panel display including the organic light emitting device, wherein a first electrode of the organic light emitting device is electrically connected to a source electrode or a drain electrode of a thin film transistor.

By using the compound represented by Formula 1 or the compound represented by Formula 2 of the present invention in an electron transport layer, a hole transport layer, or a light emitting layer of an organic light emitting device, an organic light emitting device exhibiting high efficiency and long lifespan characteristics can be implemented.

1 is a diagram schematically illustrating a structure of an organic light emitting diode according to an exemplary embodiment.

According to one aspect of the present invention, a first electrode; a second electrode; and an organic layer interposed between the first electrode and the second electrode.

An organic light emitting device is provided, wherein the organic layer includes a compound of Formula 1 or a compound of Formula 2:

<Formula 1>

<Formula 2>

In Formula 1 and Formula 2,

R ₁ , R ₂ , R ₂₁ and R ₂₂ are each independently deuterium, a substituted or unsubstituted C 1 to C 60 alkyl group, a substituted or unsubstituted C 3 to C 60 cycloalkyl group, a substituted or unsubstituted C 6 to C 6 an aryl group of 60, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted condensed polycyclic group having 6 to 30 carbon atoms, a fluorine group, -CF ₃ or a cyano group;

R ₃ to R ₁₂ and R ₂₃ to R ₃₄ are each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C 1 to C 60 alkyl group, a substituted or unsubstituted C 2 to C 60 alkenyl group, substituted or an unsubstituted C 3 to C 60 cycloalkyl group, a substituted or unsubstituted C 3 to C 60 cycloalkenyl group, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted C 3 to C 60 cyclo an alkenyl group, a substituted or unsubstituted C 3 to C 60 heteroaryl group, or a substituted or unsubstituted C 6 to C 30 condensed polycyclic group.

The organic light emitting device including the compound of Formula 1 or Formula 2 has the effect of improving device lifespan due to the high stability and high efficiency characteristics of the compound of Formula 1 or Formula 2 .

The substituents in the compounds of Formulas 1 and 2 will be described in more detail.

According to one embodiment of the present invention, in Formulas 1 and 2, _{two adjacent substituents among R 3} to R ₁₂ and R ₂₃ to R ₃₄ may be connected to form a ring.

According to another embodiment of the present invention, in Formulas 1 and 2, R ₁ , R ₂ , R ₂₁ and R ₂₂ are each independently —CN, —CF ₃ , or any one of Formulas 2a to 2e can:

In Formulas 2a to 2e,

Q ₁ represents -CR ₃₀ R ₃₁ -, -NR ₃₂ -, -S-, or -O-;

Z ₁ , R _{30 To} R ₃₂ are a hydrogen atom, deuterium, halogen, —CN, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, a substituted or unsubstituted C atoms an arylamine group having 6 to 20, or a substituted or unsubstituted heteroaryl group having 6 to 20 carbon atoms;

Y ₁ to Y ₃ are C or N;

p is an integer from 1 to 7; * indicates a bond.

를 형성할 수 있다:According to another embodiment of the present invention, in Formula 1, R ₁₁ and R ₁₂ are connected to each other,

can form:

In the above formula, A ₁ and A ₂ each independently represent hydrogen, deuterium, halogen, -CN, and the following formula 3a or 3b

In Formulas 3a and 3b,

Y ₁ is C or N; * indicates a bond.

일 수 있다:According to another embodiment of the present invention, in Formula 2, R ₂₄ , R ₂₅ , R ₂₈ and R ₂₉ are each independently —CN, a substituted or unsubstituted C 1 to C 20 alkyl group, or

It can be:

In the above formula, Z ₁ is a hydrogen atom, deuterium, halogen, -CN, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, substituted or unsubstituted C 6 to an arylamine group of 20, or a substituted or unsubstituted heteroaryl group having 6 to 20 carbon atoms;

Y ₁ is C or N; p is an integer from 1 to 4; * indicates a bond.

According to another embodiment of the present invention, in Formulas 1 and 2, R ₃ , R ₆ , R ₇ , R ₁₀ , R ₂₃ , R ₂₆ , R ₂₇ and R ₃₀ are each independently hydrogen, or deuterium can be

According to another embodiment of the present invention, in Formula 2, R ₃₁ , R ₃₂ , R ₃₃ and R ₃₄ may each independently be hydrogen, deuterium, or a substituted or unsubstituted C 1 to C 20 alkyl group, , for example, R ₃₁ , R ₃₂ , R ₃₃ and R ₃₄ may each independently be hydrogen or methyl.

Hereinafter, the definitions of representative substituents among the substituents used in the present specification are as follows (the number of carbon atoms limiting the substituents is non-limiting and does not limit the characteristics of the substituents, and substituents not defined in this specification are general to those skilled in the art. It is defined as a bar that is recognized as

unsubstituted carbon number of 1 to 60 Alkyl groups can be linear and branched, non-limiting examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, heptyl, octyl, nonanyl, dodecyl, and the like. , at least one hydrogen atom of the alkyl group is a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, or having 1 to 10 carbon atoms Alkyl group, having 1 to 10 carbon atoms An alkoxy group, having 2 to 10 carbon atoms Alkenyl group, having 2 to 10 carbon atoms an alkynyl group, an aryl group having 6 to 16 carbon atoms, and an aryl group having 4 to 16 carbon atoms It may be substituted with a heteroaryl group, or an organosilyl group.

The unsubstituted alkenyl group having 2 to 60 carbon atoms means that it contains at least one carbon double bond in the middle or at the extreme end of the unsubstituted alkyl group. Examples include ethenyl, propenyl, butenyl and the like. At least one hydrogen atom of these unsubstituted alkenyl groups may be substituted with the same substituents as in the case of the above-described substituted alkyl group.

The unsubstituted alkynyl group having 2 to 60 carbon atoms means that it contains at least one carbon triple bond at the middle or the end of the alkyl group as defined above. Examples include acetylene, propylene, phenylacetylene, naphthylacetylene, isopropylacetylene, t-butylacetylene, and diphenylacetylene. At least one hydrogen atom among these alkynyl groups may be substituted with the same substituents as in the case of the above-described substituted alkyl group.

The unsubstituted cycloalkyl group having 3 to 60 carbon atoms refers to an alkyl group having 3 to 60 carbon atoms, and at least one hydrogen atom in the cycloalkyl group may be substituted with the same substituent as the substituent of the above-described C 1 to C 60 alkyl group. Do.

An unsubstituted alkoxy group having 1 to 60 carbon atoms is -OA (here, A is an unsubstituted carbon number of 1 to 60 carbon atoms as described above) alkyl group), and non-limiting examples thereof include methoxy, ethoxy, propoxy, isopropyloxy, butoxy, pentoxy, and the like. At least one hydrogen atom among these alkoxy groups may be substituted with the same substituent as in the case of the above-described alkyl group.

An unsubstituted C 5 to C 60 aryl group refers to a carbocyclic aromatic system including one or more rings, and when it may have two or more rings, it may be fused to each other or connected through a single bond or the like. The term aryl includes aromatic systems such as phenyl, naphthyl, and anthracenyl. In addition, one or more hydrogen atoms of the aryl group may be substituted with the same substituent as the substituent of the aforementioned alkyl group having 1 to 60 carbon atoms.

Examples of the substituted or unsubstituted aryl group having 5 to 60 carbon atoms include a phenyl group, and 1 to 10 carbon atoms. Alkylphenyl group (eg, ethylphenyl group), halophenyl group (eg, o-, m- and p-fluorophenyl group, dichlorophenyl group), cyanophenyl group, dicyanophenyl group, trifluoromethoxyphenyl group, biphenyl group , halobiphenyl group, cyanobiphenyl group, having 1 to 10 carbon atoms Alkyl biphenyl group, having 1 to 10 carbon atoms Alkoxybiphenyl group, o-, m-, and p-tolyl group, o-, m- and p-cumenyl group, mesityl group, phenoxyphenyl group, (α,α-dimethylbenzene)phenyl group, (N,N'- Dimethyl) aminophenyl group, (N,N'-diphenyl) aminophenyl group, pentarenyl group, indenyl group, naphthyl group, halonaphthyl group (eg, fluoronaphthyl group), having 1 to 10 carbon atoms Alkylnaphthyl group (eg, methylnaphthyl group), having 1 to 10 carbon atoms Alkoxynaphthyl group (eg, methoxynaphthyl group), cyanonaphthyl group, anthracenyl group, azurenyl group, heptarenyl group, acenaphthylenyl group, phenarenyl group, fluorenyl group, anthraquinolyl group, methylane Triphenyl group, phenanthryl group, triphenylene group, pyrenyl group, chrysenyl group, ethyl-chrysenyl group, picenyl group, perylenyl group, chloroperylenyl group, pentaphenyl group, pentacenyl group, tetraphenylenyl group, hexa and a phenyl group, a hexacenyl group, a rubycenyl group, a coroneryl group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a pyranthrenyl group, and an ovarenyl group.

An unsubstituted heteroaryl group having 3 to 60 carbon atoms includes 1, 2, or 3 heteroatoms selected from N, O, P or S, and when it has two or more rings, they are fused to each other or connected through a single bond. can unsubstituted carbon number of 4 to 60 Examples of the heteroaryl group include a pyrazolyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a tria Zinyl group, carbazolyl group, indolyl group, quinolinyl group, isoquinolinyl group, dibenzothiophene group, etc. are mentioned. In addition, one or more hydrogen atoms in the heteroaryl group may be substituted with the same substituent as the substituent of the aforementioned alkyl group having 1 to 60 carbon atoms.

The unsubstituted aryloxy group having 5 to 60 carbon atoms is a group represented by _{-OA 1 , wherein A 1} is the aryl group having 5 to 60 carbon atoms. Examples of the aryloxy group include a phenoxy group. At least one hydrogen atom of the aryloxy group may be substituted with the same substituent as the substituent of the aforementioned alkyl group having 1 to 60 carbon atoms.

The unsubstituted arylthio group having 5 to 60 carbon atoms is a group represented by _{-SA 1 , wherein A 1} is the aryl group having 5 to 60 carbon atoms. Examples of the arylthio group include a benzenethio group, a naphthylthio group, and the like. At least one hydrogen atom in the arylthio group may be substituted with the same substituent as the substituent of the aforementioned alkyl group having 1 to 60 carbon atoms.

unsubstituted carbon number of 6 to 60 Condensed polycyclic group refers to a substituent including two or more rings in which one or more aromatic rings and one or more non-aromatic rings are fused to each other or a substituent having an unsaturated group in the ring but not having a conjugated structure. It is distinguished from an aryl group or a heteroaryl group in that it does not have.

The arylamine group means that 1, 2 or 3 aryl groups are bonded to N.

Specific examples of the compound represented by Formula 1 of the present invention include the following compounds, but are not limited thereto.

Specific examples of the compound represented by Formula 2 of the present invention include, but are not limited to, the following compounds.

The organic layer of the organic light emitting diode according to an aspect of the present invention is a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time (hereinafter 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 an electron transport function and an electron injection function (hereinafter referred to as “E-functional layer”) may include at least one of

More specifically, the organic layer may be an electron transport layer, a hole transport layer, or a light emitting layer.

According to one 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 a functional layer having both hole injection and hole transport functions, and the light emitting layer is known of an anthracene-based compound, an arylamine-based compound, or a styryl-based 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 a functional layer having both hole injection and hole transport functions, and Any one of the red layer, the green layer, the blue layer, or the white layer may include a phosphorescent compound, and the hole injection layer, the hole transport layer, or the functional layer having a hole injection function and a hole transport function at the same time, in addition to the hole transport compound It may further include a charge generating material. Meanwhile, the charge generating material may be a p-dopant, and the p-dopant may be a quinone derivative, a metal oxide, or a cyano group-containing compound.

According to 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 term “organic layer” refers to a single and/or a plurality of layers interposed between the first electrode and the second electrode of the organic light emitting device.

The organic layer may include an emission layer, and the compound may be included in the emission layer. or the organic layer includes at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time (hereinafter referred to as "H-functional layer"), and the hole The compound may be included in at least one of an injection layer, a hole transport layer, and a functional layer having a hole injection function and a hole transport function at the same time (hereinafter, referred to as an “H-functional layer”).

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

As the substrate (not shown), a substrate used in a conventional organic light emitting device may be used, and a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, handling easiness and waterproofness may be used.

The first electrode may be formed by providing a material for the first electrode on a substrate using a deposition method or a sputtering method. When the first electrode is an anode, the material for the first electrode may be selected from materials having a high work function to facilitate hole injection. The first electrode may be a reflective electrode or a transmissive electrode. As the material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, may be used. Alternatively, magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. One electrode may be formed as a reflective electrode.

The first electrode may have a single layer or a multilayer structure of two or more. For example, the first electrode may have a three-layer structure of ITO/Ag/ITO, but is not limited thereto.

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, or an electron injection layer.

The hole injection layer HIL may be formed on the first electrode by using various methods such as a vacuum deposition method, a spin coating method, a casting method, a LB method, and the like.

In the case of forming the hole injection layer by vacuum deposition, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal characteristics of the target hole injection layer, etc., but for example, the deposition temperature of about 100 to It may be selected in the range of about 500° C., a vacuum degree of about 10 ⁻⁸ to about 10 ⁻³ torr, and a deposition rate of about 0.01 to about 100 Å/sec, but is not limited thereto.

In the case of forming the hole injection layer by spin coating, the coating conditions are different depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the desired hole injection layer, but coating at about 2000 rpm to about 5000 rpm The rate, the heat treatment temperature for removing the solvent after coating may be selected from a temperature range of about 80°C to 200°C, but is not limited thereto.

As the hole injecting material, a known hole injecting material may be used. As the known hole injecting material, for example, N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-) tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl- 4,4'-diamine: DNTPD), phthalocyanine compounds such as copper phthalocyanine, m-MTDATA [4,4',4''-tris (3-methylphenylphenylamino) triphenylamine], NPB (N,N'-di (1- Naphthyl)-N,N'-diphenylbenzidine (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)), TDATA, 2-TNATA, Pani/DBSA (Polyaniline/Dodecylbenzenesulfonic acid: polyaniline /dodecylbenzenesulfonic acid), PEDOT/PSS (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate):poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)), Pani /CSA (Polyaniline/Camphor sulfonicacid:polyaniline/camphorsulfonic acid) or PANI/PSS (Polyaniline)/Poly(4-styrenesulfonate):polyaniline)/poly(4-styrenesulfonate)), etc., but are limited thereto no:

The hole injection layer may have a thickness of about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å. When the thickness of the hole injection layer satisfies the above range, a satisfactory level of hole injection characteristics may be obtained without a substantial increase in driving voltage.

Next, the hole transport layer (HTL) may be formed on the hole injection layer by using various methods such as a vacuum deposition method, a spin coating method, a casting method, a LB method, and the like. When the hole transport layer is formed by the vacuum deposition method or the spin method, the deposition conditions and coating conditions vary depending on the compound used, but in general, they may be selected from within the same range of conditions as those for the hole injection layer formation.

As the hole transport material, a compound according to an embodiment of the present invention or a known hole transport material may be used. 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), TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine (4,4',4"-tris(N- carbazolyl)triphenylamine)), NPB (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)) and the like, but is not limited thereto.

The hole transport layer may have a thickness of about 50 Å to about 2000 Å, for example, about 100 Å to about 1500 Å. When the thickness of the hole transport layer satisfies the above range, a satisfactory level of hole transport characteristics may be obtained without a substantial increase in driving voltage.

The H-functionality (a functional layer having a hole transport function at the same time) may include at least one material from among the hole injection layer material and the hole transport layer material as described above, and the thickness of the H-functional layer is about 500 Å to about 10000 Å, For example, it may be from about 100 Angstroms to about 1000 Angstroms. When the thickness of the H-functional layer satisfies the above-described range, satisfactory hole injection and aqueous properties may be obtained without a substantial increase in driving voltage.

Meanwhile, at least one of the hole injection layer, the hole transport layer, and the H-functional layer may include at least one of a compound represented by the following Chemical Formula 300 and a compound represented by the following Chemical Formula 350:

<Formula 300>

<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 may each independently represent an integer of 0 to 5, or 0, 1, or 2. For example, e may be 1 and f may be 0, but is not limited thereto.

In Formulas 300 and 350, R ₅₁ to R ₅₈ , R ₆₁ to R _{69 ,} and R ₇₁ and R ₇₂ are each independently hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, and an amidino group. group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted substituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₆₀ cycloalkyl group, substituted or unsubstituted C ₅ -C ₆₀ aryl group, substituted Or it may be an unsubstituted C ₅ -C ₆₀ aryloxy group, or a substituted or unsubstituted C ₅ -C ₆₀ arylthio group. For example, the R ₅₁ to R ₅₈ , R ₆₁ to R ₆₉ and R ₇₁ and R ₇₂ are each independently selected from hydrogen; heavy hydrogen; halogen atom; 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; phosphoric acid or a salt thereof; C ₁ -C ₁₀ alkyl group (eg, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc.); C ₁ -C ₁₀ alkoxy group (eg, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, etc.); _{C 1} -C substituted with at least one of deuterium, a halogen atom, a 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, and phosphoric acid or a salt thereof ₁₀ alkyl groups and C ₁ -C ₁₀ alkoxy groups; phenyl group; naphthyl group; anthryl group; fluorenyl group; pyrenyl group; Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C ₁ -C ₁₀ alkyl group and C ₁ a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, and a pyrenyl group substituted with one or more of -C _{10 alkoxy groups;} may be one, but is not limited thereto.

In Formula 300, R ₅₉ is a phenyl group; naphthyl group; anthryl group; biphenyl group; pyridyl group; and deuterium, a halogen atom, a 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, phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ - a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, and a pyridyl group substituted with at least one of a C ₂₀ alkyl group and a substituted or unsubstituted C ₁ -C _{20 alkoxy group;} can be one of

According to one embodiment, the compound represented by Chemical Formula 300 may be represented by the following Chemical Formula 300A, but is not limited thereto:

<Formula 300A>

_{For detailed descriptions of R 51} , R ₆₀ , R ₆₁ and R ₅₉ in 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 may include a known hole injection material, a known hole transport material and/or a material having both a hole injection function and a hole transport function as described above, the conductivity of the film It may further include a charge-generating material to improve the like.

The charge-generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, or a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of the p-dopant include tetracyanoquinonedimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane quinone derivatives such as phosphorus (F4-CTNQ) and the like; metal oxides such as tungsten oxide and molybdenum oxide; or a cyano group-containing compound such as the following compound 200, but is not limited thereto.

<Compound 200> <F4-CTNQ>

When the hole injection layer, the hole transport layer or the H-functional layer further comprises the charge-generating material, the charge-generating material is homogeneous in the hole injection layer, the hole transport layer or the H-functional layer. ) may be dispersed, or may be non-uniformly distributed, etc., various modifications are possible.

A buffer layer may be interposed between at least one of the hole injection layer, the hole transport layer, and the H-functional layer and the emission layer. The buffer layer may serve to increase efficiency by compensating for an optical resonance distance according to a wavelength of light emitted from the light emitting layer. The buffer layer may include a known hole injection material or a hole transport material. Alternatively, the buffer layer may include the same material as one of the materials included in the hole injection layer, the hole transport layer, and the H-functional layer formed under the buffer layer.

Then, the light emitting layer (EML) may be 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 casting method, a LB method, or the like. In the case of forming the light emitting layer by vacuum deposition and spin coating, the deposition conditions vary depending on the compound used, but in general, it may be selected from a range of conditions substantially the same as those of the hole injection layer.

The light emitting layer may include the compound according to the present invention. In addition to the compound represented by Formula 1 or Formula 2, the light emitting layer may be formed using a variety of known light emitting materials, and may be formed using a known host and dopant. In the case of the dopant, both a known fluorescent dopant and a known phosphorescent dopant may be used.

For example, as known hosts, Alq ₃ , CBP (4,4′-N,N′-dicarbazole-biphenyl), PVK (poly(n-vinylcarbazole)), 9,10-di(naphthalene) -2-yl) anthracene (ADN), TCTA, TPBI (1,3,5-tris (N-phenylbenzimidazol-2-yl) benzene (1,3,5-tris (N-phenylbenzimidazole-2-yl) )benzene)), TBADN (3-tert-butyl-9,10-di(naph-2-yl) anthracene), E3, DSA (distyrylarylene), dmCBP (refer to the following formula), the following compounds 501 to 509 may be used, but is not limited thereto.

PVK ADN

Alternatively, as the host, an anthracene-based compound represented by the following Chemical Formula 400 may be used:

<Formula 400>

In Formula 400, Ar ₁₁₁ and Ar ₁₁₂ are each independently a substituted or unsubstituted C ₅ -C ₆₀ arylene group; wherein Ar ₁₁₃ to Ar ₁₁₆ are each independently a substituted or unsubstituted C ₁ -C ₁₀ alkyl group or a substituted or unsubstituted C ₅ -C ₆₀ aryl group; g, h, i and j may each independently be an integer from 0 to 4.

For example, in Formula 400, Ar ₁₁₁ and Ar ₁₁₂ may represent a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group; or a phenylene group, a naphthylene group, a phenanthrenylene group, a fluorenyl group, or a pyrenylene group substituted with at least one of a phenyl group, a naphthyl group, and an anthryl group, but is not limited thereto.

In Formula 400, g, h, i, and j may each independently be 0, 1, or 2.

중 하나일 수 있으나, 이에 한정되는 것은 아니다.In Formula 400, Ar ₁₁₃ to Ar _{116 may each independently represent a C 1} -C ₁₀ alkyl group substituted with at least one of a phenyl group, a naphthyl group, and an anthryl group; phenyl group; naphthyl group; anthryl group; pyrenyl group; phenanthrenyl group; fluorenyl group; Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or its salt, sulfonic acid group or its salt, phosphoric acid or its salt, C ₁ -C ₆₀ alkyl group, C ₂ A _{phenyl group substituted with at least one of a -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 group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group, a naphthyl group, an anthryl group, a pyrenyl group, a phenanthrenyl group and a fluorenyl group; and

may be one, but is not limited thereto.

For example, the anthracene-based compound represented by Formula 400 may be one of the following compounds, but is not limited thereto:

Alternatively, as the host, an anthracene-based compound represented by the following Chemical Formula 401 may be used:

<Formula 401>

_{Ar 122 in} Formula 401 _{For a detailed description of Ar 125} to Ar 125 , refer to the description of Ar ₁₁₃ in Formula 400 above.

_{Ar 126} and Ar ₁₂₇ in Formula 401 may each independently represent a C ₁ -C ₁₀ alkyl group (eg, a methyl group, an ethyl group, or a propyl group).

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

For example, the anthracene-based compound represented by Formula 401 may be one of the following compounds, but is not limited thereto:

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

Meanwhile, 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).

DPAVBi

TBPe

For example, the following compounds may be used as the red dopant, but the present invention is not limited thereto.

For example, the following compounds may be used as the green dopant, but the present invention is not limited thereto.

Meanwhile, the dopant that may be included in the emission layer may be a Pt-complex as described below, but is not limited thereto:

In addition, the dopant that may be included in the light emitting layer may be a known Os-complex as follows, but is not limited thereto:

When the light emitting layer includes a host and a dopant, the content of the dopant may be generally selected from about 0.01 to about 15 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

The light emitting layer may have a thickness of about 100 Å to about 1000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light emitting layer satisfies the above range, excellent light emitting characteristics may be exhibited without a substantial increase in driving voltage.

Next, an electron transport layer (ETL) is formed on the light emitting layer using various methods such as vacuum deposition, spin coating, and casting. In the case of forming the electron transport layer by the vacuum deposition method and the spin coating method, the conditions may vary depending on the compound used, but in general, it may be selected from a range of conditions substantially the same as those for the formation of the hole injection layer.

As the material for the electron transport layer, a known electron transport material may be used in addition to the compound according to the present invention as it functions to stably transport electrons injected from the electron injection electrode (Cathode). Examples of known electron transport materials include quinoline derivatives, in particular tris(8-quinolinolate)aluminum (Alq3), TAZ, Balq, beryllium bis(benzoquinolin-10- olate: Bebq ₂ ), ADN, compound 201, compound 202, etc. may be used, but is not limited thereto.

<Compound 201> <Compound 202>

BCP

The electron transport layer may have a thickness of about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer satisfies the above range, a satisfactory electron transport characteristic may be obtained without a substantial increase in driving voltage.

Alternatively, the electron transport layer may further include a metal-containing material in addition to the known electron transporting organic compound.

The metal-containing material may include a Li complex. Non-limiting examples of the Li complex include lithium quinolate (LiQ) or compound 203 below:

<Compound 203>

In addition, an electron injection layer (EIL), which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, and the material is not particularly limited.

As the material for forming the electron injection layer, any known material for forming the electron injection layer such as _{LiF, NaCl, CsF, Li 2 O, BaO, and the like may be used.} Although the deposition conditions of the electron injection layer vary depending on the compound used, in general, the electron injection layer may be selected from the same range of conditions as those for the formation of the hole injection layer.

The electron injection layer may have a thickness of about 1 Å to about 100 Å, and about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the above range, a satisfactory level of electron injection characteristics may be obtained without a substantial increase in driving voltage.

A second electrode is provided above the organic layer. The second electrode may be a cathode, which is an electron injection electrode. In this case, as the metal for forming the second electrode, a metal having a low work function, an alloy, an electrically conductive compound, and a mixture thereof may be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. A transmissive electrode can be obtained by forming it as a thin film. On the other hand, in order to obtain a top light emitting device, various modifications are possible, such as forming a transmissive electrode using ITO and IZO.

In the above, the organic light emitting device has been described with reference to FIG. 1, but is not limited thereto.

In addition, when a phosphorescent dopant is used for the light emitting layer, in order to prevent the phenomenon of triplet excitons or holes from being diffused into the electron transport layer, between the hole transport layer and the light emitting layer or between the H-functional layer and the light emitting layer vacuum deposition method, spin coating method, The hole blocking layer (HBL) may be formed using a method such as a casting method or an LB method. In the case of forming the hole blocking layer by the vacuum deposition method and the spin coating method, the conditions may vary depending on the compound used, but in general, it may be within the range of substantially the same conditions as those for the formation of the hole injection layer. A known hole blocking material can also be used, and examples thereof include oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives. For example, the following BCP may be used as the hole blocking layer material.

The hole blocking layer may have a thickness of about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the above range, excellent hole blocking characteristics can be obtained without a substantial increase in driving voltage.

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

In addition, the organic layer of the organic light emitting device according to an embodiment of the present invention may be formed by a deposition method using a compound according to an embodiment of the present invention, or a compound according to an embodiment of the present invention prepared as a solution. It can also be formed by a wet method of coating.

Hereinafter, an organic light emitting device according to an embodiment of the present invention will be described in more detail by way of Synthesis Examples and Examples, but the present invention is not limited to the following Synthesis Examples and Examples.

[Example]

Synthesis example

The organic light emitting device according to the present invention exhibited excellent I-V-L characteristics with improved driving voltage and improved efficiency compared to the device of Comparative Example, and exhibited a result of significantly improving lifespan due to excellent lifespan improvement effect. Representative characteristics and lifetime results are summarized in Table 1 below.

Although the present invention has been described with reference to the above synthesis examples and examples, these are merely exemplary, and those of ordinary skill in the art to which the present invention pertains can make various modifications and equivalent other examples therefrom. will understand Therefore, the true technical protection scope of the present invention should be determined by the technical spirit of the appended claims.

Claims (20)

a first electrode;
a second electrode; and
An organic light emitting device having an organic layer interposed between the first electrode and the second electrode,
An organic light emitting device in which the organic layer includes a compound of Formula 1 or a compound of Formula 2:
<Formula 1>

<Formula 2>

In Formula 1 and Formula 2,
R ₁ , R ₂ , R ₂₁ and R ₂₂ are each independently deuterium, a substituted or unsubstituted C 1 to C 60 alkyl group, a substituted or unsubstituted C 3 to C 60 cycloalkyl group, a substituted or unsubstituted C 6 to C 6 an aryl group of 60, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted condensed polycyclic group having 6 to 30 carbon atoms, a fluorine group, -CF ₃ or a cyano group;
R ₃ to R ₁₂ and R ₂₃ to R ₃₄ are each independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C 1 to C 60 alkyl group, a substituted or unsubstituted C 2 to C 60 alkenyl group, substituted or an unsubstituted C 3 to C 60 cycloalkyl group, a substituted or unsubstituted C 3 to C 60 cycloalkenyl group, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or unsubstituted C 3 to C 60 cyclo An alkenyl group, a substituted or unsubstituted C 3 to C 60 heteroaryl group, or a substituted or unsubstituted C 6 to C 30 condensed polycyclic group,
Two adjacent substituents of R ₃ to R ₁₂ are connected to form a ring. The method of claim 1,
In Formula 2, an organic light-emitting device in which two adjacent substituents of _{R 23} to R _{34 are connected to form a ring.} The method of claim 1,
In Formulas 1 and 2, R ₁ , R ₂ , R ₂₁ and R ₂₂ are each independently —CN, —CF ₃ , or an organic light emitting diode of any one of Formulas 2a to 2e:

In Formulas 2a to 2e,
Q ₁ represents -CR ₃₀ R ₃₁ -, -NR ₃₂ -, -S-, or -O-;
Z ₁ , Z ₂ , R ₃₀ to R ₃₂ are hydrogen atom, deuterium, halogen, —CN, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, substituted or unsubstituted a cyclic arylamine group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 6 to 20 carbon atoms;
Y ₁ to Y ₃ are CH or N;
p is an integer from 1 to 7;
* indicates a bond. The method of claim 1,
In Formula 1, R ₁₁ and R ₁₂ are connected to each other

An organic light emitting device to form:
In the above formula, A ₁ and A ₂ each independently represent hydrogen, deuterium, halogen, -CN, and the following formula 3a or 3b

In Formulas 3a and 3b,
Y ₁ is CH or N;
* indicates a bond. The method of claim 1,
In Formula 2, R ₂₄ , R ₂₅ , R ₂₈ and R ₂₉ are each independently —CN, a substituted or unsubstituted C 1 to C 20 alkyl group, or

Phosphorus organic light emitting device:
In the above formula, Z ₁ is a hydrogen atom, deuterium, halogen, -CN, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 20 aryl group, substituted or unsubstituted C 6 to an arylamine group of 20, or a substituted or unsubstituted heteroaryl group having 6 to 20 carbon atoms;
Y ₁ is CH or N;
p is an integer from 1 to 4;
* indicates a bond. The method of claim 1,
In Formulas 1 and 2, R ₃ , R ₆ , R ₇ , R ₁₀ , R ₂₃ , R ₂₆ , R ₂₇ and R ₃₀ are each independently hydrogen or deuterium. The method of claim 1,
In Formula 2, R ₃₁ , R ₃₂ , R ₃₃ and R ₃₄ are each independently hydrogen, deuterium, or a substituted or unsubstituted C 1 to C 20 alkyl group. The method of claim 1,
In Formula 2, R ₃₁ , R ₃₂ , R ₃₃ and R ₃₄ are each independently hydrogen or methyl. a first electrode; a second electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes any one of the following compounds:

The method of claim 1,
An organic light emitting device wherein the organic layer is an electron transport layer, a hole transport layer, or a light emitting layer. The method of claim 1,
The organic light emitting device includes a light emitting layer, a hole injection layer, a hole transport layer, or a functional layer having both hole injection and hole transport functions,
Any one of the red layer, the green layer, the blue layer, and the white layer of the emission layer includes a phosphorescent compound. 12. The method of claim 11,
The hole injection layer, the hole transport layer, or the functional layer having both a hole injection function and a hole transport function includes a charge generating material. 13. The method of claim 12,
An organic light emitting device wherein the charge generating material is a p-dopant. 14. The method of claim 13,
An organic light-emitting device wherein the p-dopant is a quinone derivative. 14. The method of claim 13,
An organic light emitting device wherein the p-dopant is a metal oxide. 14. The method of claim 13,
An organic light emitting device wherein the p-dopant is a cyano group-containing compound. The method of claim 1,
The organic light emitting device in which the organic layer includes an electron transport layer, and the electron transport layer includes a metal complex. 18. The method of claim 17,
The organic light-emitting device wherein the metal complex is lithium quinolate (LiQ) or compound 203 below.
<Compound 203>

The method of claim 1,
An organic light emitting device in which the organic layer is formed by a wet process using the compound of Formula 1 or Formula 2. A flat panel display comprising the organic light emitting device of claim 1 or 9, wherein a first electrode of the organic light emitting device is electrically connected to a source electrode or a drain electrode of a thin film transistor.

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