KR20140072295A - Deuteriated organometallic complex and organic light-emitting diode including the same - Google Patents

Abstract

The present invention relates to a deuterium-substituted organic metal complex and an organic light-emitting diode including the same. In particular, the present invention relates to a deuterium-substituted organic metal complex represented by [Chemical Formula A] and an organic light-emitting diode including the same. [Chemical Formula A]

Description

[0001] The present invention relates to an organometallic complex substituted with deuterium and an organic light emitting device including the same.

The present invention relates to a deuterium-substituted organometallic complex and an organic light emitting device including the same, and more particularly, to an organic metal complex having a long-life characteristic and excellent in light emission characteristics such as a driving voltage and a current efficiency, Device.

In recent years, the demand for a flat display device having a small space occupation has been increasing due to the enlargement of a display device. The liquid crystal display, which is a typical flat display device, has an advantage of being lighter than a conventional CRT (cathode ray tube) angle is limited and a back light is necessarily required. In contrast, an organic light emitting diode (OLED), a new flat display device, is a display using an auto-luminescent phenomenon and has advantages such as a large viewing angle, a light weight and a small size compared to a liquid crystal display, In recent years, application to a full-color display or illumination is expected.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.

An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight and may be classified into a fluorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host-dopant system can be used as a light-emitting material in order to increase the light-emitting efficiency through the light-emitting layer.

When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant used.

In order for the organic luminescent device to sufficiently exhibit the above-described excellent characteristics, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a luminescent material, an electron transporting material and an electron injecting material is supported by a stable and efficient material Should be preceded.

On the other hand, studies have been made to introduce a deuterium-substituted compound as the organic material in order to improve the efficiency and stability of the organic light emitting device.

Compounds substituted with deuterium are known to exhibit differences in thermodynamic behavior compared to compounds bonded with hydrogen because the atomic mass of deuterium is two times greater than hydrogen resulting in lower zero energy and lower vibration energy levels Because. In addition, physicochemical properties such as chemical bond lengths related to deuterium appear to be different from hydrogen, and in particular, the CD bond elongation amplitude is smaller than that of CH bonds, so that the van der Waals radius of deuterium is smaller than hydrogen, Indicating that the bond is shorter and stronger than the CH bond.

In addition, when substituted with deuterium, the energy of the bottom state is lowered. As the bond length of deuterium and carbon becomes shorter, the molecular hardcore volume is reduced, and thus, the electro polar polarizability can be reduced, It is known that the thin film volume can be increased by weakening the intermolecular interaction. These properties can make the crystallinity of the thin film lower, that is, amorphous state, and can generally be effective for increasing OLED lifetime and driving characteristics, and the heat resistance can be further improved.

As a conventional technique related to the organic compound layer for an organic light emitting device including the deuterium, Japanese Patent Application Laid-Open No. 10-1111406 discloses a method of replacing an amine compound containing a carbazole with deuterium or mixing a deuterium- And a technique for providing a driving and a long-life element, and Japanese Patent Laid-Open No. 10-1068224 discloses a technique using a host as an anthracene derivative containing a phenyl group in which hydrogen in the phenyl group is substituted with deuterium.

However, in spite of efforts to manufacture the long-life device, there is a continuing need to develop an organic material layer for an organic light emitting device that is stable, efficient, and has a long life.

Patent Registration No. 10-1111406 (Apr. 12, 2012)

Korean Patent Registration No. 10-1068224 (September 28, 2011)

Therefore, the first technical object of the present invention is to provide an organometallic compound for an organic light emitting device which can be used for an electron transport layer or an organic light emitting layer and has a long life.

A second object of the present invention is to provide an organic light emitting device including the organic metal compound.

In order to achieve the first technical object of the present invention, there is provided an organometallic compound which can be used for an electron transport layer or a light emitting layer of an organic light emitting device.

(A)

In the above formula (A)

R ₂ to R ₇ are the same or different from each other and independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms , A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted 5 A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S, a substituted or unsubstituted hetero atom, a substituted Is a group consisting of an unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted silane group, a carbonyl group, a phosphoryl group, an amino group, a nitrile group, a hydroxyl group, a nitro group, a halogen group, an amide group and an ester group And may form a condensed ring of aliphatic, aromatic, aliphatic hetero or aromatic hetero with adjacent groups;

The substituent R ₂ And R < ₇ > are deuterium;

All hydrogen place included in the substituents R ₂ to R ₇ are to the substituent R ₂ in the case of substituents other than hydrogen or deuterium, R ₇ may be replaced by deuterium.

According to another aspect of the present invention, there is provided an organic light emitting display comprising a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode, An organic light emitting device comprising at least one organometallic compound represented by the formula (A).

According to the present invention, the organometallic compound represented by the formula (A) can be improved in heat resistance as compared with the existing material, has a long life, and can have stable and excellent device characteristics.

1 is a schematic view of an organic light emitting device according to an embodiment of the present invention.
2 is a graph showing a nuclear magnetic resonance spectrum of an organometallic compound according to one embodiment of the present invention.

Hereinafter, the present invention will be described in more detail.

The present invention provides a compound represented by the following formula (A) as an organometallic compound that can be used in an electron transporting layer or a light emitting layer of an organic light emitting device.

  (A)

In the above formula (A)

R ₂ to R ₇ are the same or different from each other and independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted hetero atom, O, N or A substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted silane group, a carbonyl group, a phosphoryl group, an amino group, a nitrile group, a hydroxyl group, a cyano group An amino group, an amino group, an amino group, an amino group, an amino group, a nitro group, a halogen group, an amide group, and an ester group;

The substituent R ₂ And R < ₇ > are deuterium;

When all of the substituents R ₂ to R ₇ are hydrogen or a substituent other than deuterium, all of the hydrogen atoms contained in the substituents R ₂ to R ₇ may be substituted with deuterium;

The 'substituted' in the above 'substituted or unsubstituted' means a group selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, , An alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms , An alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, Group, and an aryloxy group having 1 to 24 carbon atoms.

An aryl group, which is a substituent used in the compound of the present invention, means a carbocyclic aromatic system containing at least one ring, and when the substituent is present, it can be fused with neighboring substituents to further form a ring.

Specific examples of the aryl group include aromatic groups such as phenyl, naphthyl, tetrahydronaphthyl and the like, and at least one hydrogen atom of the aryl group may be substituted with a substituent such as a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, An amino group (-NH 2, -NH (R), -N (R ') (R "), R' and R" are each independently an alkyl group having 1 to 10 carbon atoms, An alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a carbonyl group having 1 to 24 carbon atoms, A heteroaryl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, or a heteroarylalkyl group having 2 to 24 carbon atoms.

The heteroaryl group, which is a substituent used in the compounds of the present invention, refers to a C 2 -C 24 ring aromatic system containing 1, 2 or 3 heteroatoms selected from N, O, P or S and the remaining ring atoms are carbon, The rings may be fused to form a ring. And at least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as the aryl group.

Specific examples of the alkyl group as a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl and the like. The atom may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, At least one hydrogen atom in the alkoxy group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the silyl group used as the substituent in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl, Butylsilyl, dimethylpurylsilyl and the like, and at least one hydrogen atom of the silyl group may be substituted with the same substituent as the aryl group.

More specifically, in the organometallic compound of the present invention, R ₂ to R ₇ in the formula [A] each independently represent hydrogen; heavy hydrogen; A halogen atom; A hydroxyl group; Cyano; A nitro group; An amino group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C2-C20 alkynyl; A substituent of the following formulas (4A) to (4H); As shown in FIG.

In the above general formulas (4A) to (4H)

Z ₁ to Z ₇ are, independently of each other, hydrogen; heavy hydrogen; A halogen atom; A hydroxyl group; Cyano; A nitro group; An amino group; An amidino group; Hydrazine; Hydrazone; A carboxyl group or a salt thereof; Sulfonic acid group or its salt; Phosphoric acid or its salts; An alkyl group having 1 to 10 carbon atoms; An alkoxy group having 1 to 10 carbon atoms; An alkylthio group having 1 to 10 carbon atoms; An alkyl group having 1 to 10 carbon atoms which is substituted with at least one of a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, An alkyl group having 1 to 10 carbon atoms and an alkylthio group having 1 to 10 carbon atoms; A phenyl group; Naphthyl group; A fluorenyl group; A phenanthrenyl group; Anthryl group; Pyrenyl; A crycenyl group; An alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a salt of a carboxyl group or a salt thereof, A phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, and a klycenyl group substituted with at least one of an alkoxy group having 1 to 10 carbon atoms and an alkylthio group having 1 to 10 carbon atoms; Indole diarrhea; A benzimidazolyl group; Carbazolyl group; Imidazolyl group; An imidazolinyl group; Imidazopyridinyl group; An imidazopyrimidinyl group; A pyridinyl group; A pyrimidinyl group; Triazinyl groups; A quinolinyl group; An alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a salt of a carboxyl group or a salt thereof, An imidazolyl group, an imidazopyridinyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, , An imidazopyrimidinyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group and a quinolinyl group; Di (alkyl having 1 to 10 carbon atoms) amino group; And an aryl group having 1 to 10 carbon atoms, and the aryl group having 6 to 10 carbon atoms is selected from the group consisting of a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, and a klycenyl group . ≪ / RTI >

In the present invention, the substituent R ₇ in the above formula (A) may be deuterium, and in this case, the substituent R ₂ may also be deuterium.

In addition, the present invention R ₂ is bonded to an aromatic ring of the compound of Formula A in the case where the substituent R ₇ in the above-mentioned [Chemical Formula A] Deuterium To R 4 substituents, at least of ₇ may be a hydrogen or deuterium, R ₂ substituent in this case may be heavy hydrogen.

In another aspect, the present invention wherein the substituents R ₂ To R < ₇ > are substituents other than hydrogen or deuterium, the substituents R < _{2 >} To R < ₇ > may be substituted with deuterium.

When the substituent R ₇ and the substituent R ₂ in the above-mentioned formula [A] are deuterium, the above-mentioned formula [A] may have 0 or 1 substituents other than hydrogen or deuterium, , The substituents are each independently of one another an alkyl group having 1 to 8 carbon atoms; A cycloalkyl group having 3 to 10 carbon atoms; An aryl group having 6 to 10 carbon atoms; A heteroaryl group having 3 to 8 carbon atoms and having 1 to 2 nitrogen, oxygen, or sulfur atoms; A silyl group having a substituent selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, and an aryl group having 6 to 10 carbon atoms, and the substituents may be deuterium have.

The formula (A) of the present invention may be any one selected from the group consisting of the following formulas (1) to (81).

Hereinafter, 'D' means deuterium, and '-D / H' means that the substituent bonded to the hydrogen position of each substituent is hydrogen or deuterium.

When driving the organic light-emitting device employing the organic metal compound in the present invention between a pair of electrodes (an anode and a cathode), the organic metal compound is formed in an organic layer between a pair of electrodes, between organic layers, The organic light emitting device employing the organic metal compound can have excellent driving voltage, efficiency, brightness, and long life time characteristics.

Hereinafter, a method for producing the organometallic compound of the present invention will be briefly described.

The compound of formula (A) of the present invention can be prepared by the following Reaction Scheme 1 and Reaction Scheme 2.

[Reaction Scheme 1]

(Wherein '-D / H' means that the substituent directly bonded to the carbon of the aromatic ring is hydrogen or deuterium).

[Reaction Scheme 2]

The above reaction scheme 1 is a step for preparing a heterocyclic compound in which a part of hydrogen in an aromatic ring is deuterium-substituted. In the above step, '-D / H' means that the substituent directly bonded to the carbon of the aromatic ring is hydrogen or deuterium.

In this case, at least one of the hydrogen sites adjacent to the hiragphenyl group (-OH) or the hydrogen sites adjacent to the nitrogen atom in the hydrogen sites bonded to the aromatic ring may be substituted with deuterium.

More specifically, the hydrogen site adjacent to the hydroxyl group (-OH) in the hydrogen atom bonded to the aromatic ring can be substituted with deuterium. In this case, the hydrogen atom adjacent to the nitrogen atom in the hydrogen atom bonded to the aromatic ring may also be substituted with deuterium.

The deuterium substitution reaction of Scheme 1 may be performed by reacting a material containing a heterocyclic compound and a deuterium source at 150 to 350 ° C in a high pressure reactor under a transition metal catalyst, and maintaining the reaction time for about 1 hour to 5 days.

Further, in the present invention, the reaction in the high-pressure reactor may be repeated two to five times in order to improve the degree of deuteration by the deuterium substitution reaction, which may be determined depending on how much the degree of deuteration of the user is adjusted .

Examples of the deuterium source used in the above Reaction Scheme 1 include heavy water (D ₂ O), d-6 acetone. d-6 Benzene. CD ₃ OD (deuterium substituted methanol), and the like, but are not limited thereto.

As the transition metal catalyst, transition metals such as Ni, Pd, Pt, and Co may be used.

The dehydrogenation catalyst may be supported on a support, and examples of the support include silica, alumina, aluminosilicate, activated carbon, and the like, but not limited to Ni on Si / Al (silica / A catalyst in which nickel is supported on alumina), Pd / C (a catalyst in which palladium is supported on activated carbon), and the like can be used.

Further, in the deuteration step, when hydrogen is heated in a solvent containing a deuterium source under an acid catalyst or when stirring is carried out under an acid catalyst, a hydrogen group (proton) bonded to the pyrene can exchange reaction with deuterium, have.

The deuterium source corresponding to the solvent used here was deuterated water (D ₂ O), d-6 acetone. d-6 Benzene. CD ₃ OD (deuterium substituted methanol), and the like, but are not limited thereto.

The heating conditions under the above-described acid catalyst may be a reaction at 40 to 200 ° C, and a reaction time is preferably 30 minutes to 3 days.

Examples of the acid catalyst used in the reaction formula 1 include, but are not limited to, inorganic acids such as hydrochloric acid and sulfuric acid, organic acids such as acetic acid and paratoluenesulfonic acid, and Lewis acids such as AlCl ₃ and EtAlCl ₂ .

In the present invention, Reaction Scheme 2 is a step of preparing a compound of Formula A by combining a deuterium-substituted heterocyclic compound with lithium. This can be easily produced by reacting a lithium salt such as lithium hydroxide (LiOH) or an organic metal compound such as lithium diisopropylamine (LDA) or alkyllithium with the deuterated hydrogenated heterocyclic compound.

Further, the compound of formula (A) of the present invention can be prepared through the following reaction formula (4) and (5).

[Reaction Scheme 4]

[Reaction Scheme 5]

In Scheme 4, a lithium-substituted organometallic compound of a heterocyclic compound is prepared by reacting a lithium hydroxide (LiOH), an organometallic lithium salt, or the like with the above-mentioned heterocyclic compound .

In the above reaction scheme 5, the obtained lithium-heterocyclic compound is dehydrogenated by reacting materials containing a deuterium source together at 150 to 350 ° C in a high-pressure reactor under a transition metal catalyst, For about 1 hour to about 5 days.

'-D / H' in the above formula (5) means that some of hydrogen is deuterium-substituted.

On the other hand, when the heterocyclic compound has substituents other than hydrogen such as aryl and alkyl, the hydrogen atoms in substituents such as aryl and alkyl may be replaced with deuterium by a deuterium substitution reaction. When the hydrogen atom contained in the substituent such as aryl or alkyl is not substituted with deuterium, a deuterium-substituted heterocyclic compound is prepared by the above method, and then a substituent such as aryl or alkyl which is not substituted with deuterium is introduced .

The compound represented by the general formula (A) of the present invention is a substituent bonded to the carbon of the aromatic ring, and includes hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxyl group having 6 to 30 carbon atoms A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted aryl group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S, Of it can comprise various substituents, can control the degree of crystallinity or an organic light emitting properties of the organic metal compound of the present invention.

The deuteration degree used in this specification will be described in detail as follows.

In general, a "deuterated derivative" of compound X means having the same structure as compound X, but with at least one D replacing H.

The terms "% deuterated" and "% deuterated" refer to the ratio of deuterium to the sum of all hydrogen and deuterium bonded directly to compound X as a percentage.

Thus, if two of the six hydrogens of benzene are deuterated, the degree of deuteration in the compound C ₆ H ₄ D ₂ is deemed to be 2 / (4 + 2) * 100 = 33% deuteration.

The degree of deuteration of the deuterium substituted in the organometallic compound in the present invention is such that the degree of deuteration of the deuterium substituted on the aromatic ring of the organometallic compound with respect to the sum of all the hydrogen directly bonded to the carbon of the aromatic ring and the sum of all deuterium bonded directly to the carbon of the aromatic ring The percentage of all deuterium directly bonded can be expressed as a percentage.

More specifically, in the case of the deuterium-substituted organometallic compound represented by the formula (A), when the compound of the above formula (A) is free of hydrogen or other substituent other than deuterium, the average number of the six hydrogen- As shown in FIG. In this case, since the number of deuterium-substituted units may differ for each individual molecule, the degree of deuteration should be indicated by calculating the degree of substitution on average.

On the other hand, when the compound of the formula (A) has one substituent, that is, in the case of the organometallic compound having one substituent such as the halogen or the methyl group, the degree of deuteration is the average value of the number of the deuterium substituted in the remaining five hydrogen- .

Therefore, when an average of 3.5 deuterium atoms is substituted, the deuteration degree of the pyrene having one halogen substituent can be represented by 3.5 * 100/5 = 70%.

In the present invention, the deuteration degree of the formula (A) may be 20% or more, preferably the deuteration degree may be 30% or more, more preferably the deuteration degree may be 40% or more, May be greater than or equal to 50%, and still more preferably, the deuteration degree may be greater than or equal to 60%, and still more preferably, the deuteration degree may be greater than or equal to 70%.

The present invention also provides a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains at least one of the organometallic compounds in the present invention.

In the present invention, the term "(organic layer) includes at least one organometallic compound" means " one organic metal compound belonging to the category of the present invention (organic layer) May contain more than one species of compound. "

 At this time, the organic layer containing the compound of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer.

In the present invention, the organic layer interposed between the first electrode and the second electrode may be a light emitting layer or an electron transporting layer. In this case, the organic metal compound may be included in the electron transporting layer, and the light emitting layer may be composed of a host and a dopant .

In the present invention, specific examples of the dopant material used in the light emitting layer include pyrene-based compounds, deuterium-substituted pyrene-based compounds, arylamines, deuterium-substituted arylamines, peryl-based compounds, deuterium- Substituted carbazole-based compound, stilbene-based compound, deuterated substituted stilbene-based compound, starburst-based compound, deuterium-substituted compound, deuterium-substituted pyrrole-based compound, hydrazone compound, deuterated substituted hydrazone compound, A starburst-based compound, an oxadiazole-based compound, a deuterium-substituted oxadiazole-based compound, coumarine, deuterium-substituted coumarine, and the like, but the present invention is not limited thereto.

As the host used in the light emitting layer, Alq3, CBP (4,4'-N, N'-dicarbazole-biphenyl), PVK (poly (n-vinylcarbazole) Naphthalene-2-yl) anthracene (ADN), TCTA, TPBI (1,3,5-tris (N-phenylbenzimidazole- yl) benzene), TBADN (3-tert-butyl-9,10-di (naphth-2-yl) anthracene), E3, DSA (distyrylarylene), dmCBP Deuterium substituents of the compounds, and the like, but the present invention is not limited thereto.

 PVK ADN

When the light emitting layer includes a host and a dopant, the dopant may be selected from the range of about 0.01 to about 20 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

In the present invention, when the organometallic compound is used in an electron transporting layer, the electron transporting layer may contain other kinds of electron transporting compounds in addition to the organometallic compound of the present invention.

Here, the compound for the electron transport layer different from the above-mentioned organometallic compound may be a compound in which the deuterium-substituted lithium salt compound has the structure of the above formula (A), but it may be a compound of a different kind or a compound for the electron transport layer Compound.

As the electron transport layer compound having no structure represented by the above formula (A), oxadiazole derivatives such as PBD, BMD, BND or Alq ₃ Etc. may be used.

When the organometallic compound in the present invention is mixed with other electron transporting compounds and used in an electron transporting layer, the mixing ratio thereof may be 1:20 to 20: 1 as a weight ratio.

In the present invention, at least one layer selected from the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer may be formed by a single molecular deposition method or a solution process, The organic light emitting element can be used for a display element, a display element, or a monochromatic or white illumination element.

Hereinafter, the organic light emitting device of the present invention will be described with reference to FIG.

1 is a cross-sectional view showing the structure of an organic light emitting device of the present invention. The organic light emitting device according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60, and a cathode 80, An injection layer 70 may be further formed. In addition, one or two intermediate layers may be further formed, or a hole blocking layer or an electron blocking layer may be further formed.

Referring to FIG. 1, the organic light emitting device of the present invention and a method of manufacturing the same will be described below. First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

A hole injection layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30.

A hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method to form a thin film on the organic light emitting layer 50 can do. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level . In this case, the hole blocking material to be used is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. Here, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

The light emitting layer may be made of a host and a dopant.

In addition, according to a specific example of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 ANGSTROM, and the light emitting layer may further include various hosts and various dopant materials.

In this case, the dopant may be a compound represented by the following Chemical Formula 1 or Chemical Formula 2.

        [Chemical Formula 1] < EMI ID =

Among the above-mentioned formulas (1) and (2)

A is a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, an optionally substituted arylene group having 6 to 60 carbon atoms , A substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms having O, N or S as a hetero atom, preferably an anthracene, pyrene, phenanthrene, indenophenanthrene, klysene, naphtha Phenylene, perylene, and pentacene.

At this time, A may be a compound represented by the following formulas (A1) to (A10).

[Formula A1] [Formula A2] [Formula A3]

[Chemical Formula A4] [Chemical Formula A5] [Chemical Formula A6]

[Chemical formula A7] [Chemical formula A8] [Chemical formula A9]

 (A10)

Wherein Z ₁ to Z ₂ in the formula [A3] are each independently selected from the group consisting of hydrogen, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted Or an unsubstituted or substituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted aryl group having 2 to 60 carbon atoms (Substituted or unsubstituted C1-C60 alkyl) amino group, or a substituted or unsubstituted C6-C60 aryl) amino group, a substituted or unsubstituted C1-C60 alkylamino group, , (Substituted or unsubstituted aryl group having 6 to 60 carbon atoms) amino group, and Z ₁ to Z ₂ are the same or different from each other and can form a condensed ring with adjacent groups.

In the above formula (1)

X ₁ and X ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a single bond, X ₁ and X ₂ may be bonded to each other,

Y ₁ and Y ₂ are each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted Or a substituted or unsubstituted C1 to C24 heteroalkyl group, a substituted or unsubstituted C3 to C24 cycloalkyl group, a substituted or unsubstituted C1 to C24 alkoxy group, a cyano group, a halogen group, a substituted or unsubstituted carbon number At least one selected from the group consisting of an aryloxy group having 6 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted 6 to 30 carbon atoms, germanium, phosphorus, boron, deuterium and hydrogen Y ₁ to Y ₂ are the same or different from each other and can form a condensed ring of aliphatic, aromatic, aliphatic hetero or aromatic hetero with groups adjacent to each other.

Each of l and m is an integer of 1 to 20, and n is an integer of 1 to 4.

In the above formula (2)

C _y is a substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, and when b is 2 or more, each cycloalkane may be in a fused form, Each of which may be substituted with deuterium or alkyl, and may be the same as or different from each other. .

Wherein B represents a single bond or - [C (R 5) ( R 6)] p - and wherein p is, and are of 1 to 3 integer, not less than p 2 2 or R ₅ and R ₆ are equal to each other or different, ;

Wherein R ₁ , R ₂ , R _{3 ,} R ₅ and R ₆ are each independently selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, knit meat, amino group, amidino group, hydrazine, hydrazone, , A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms Substituted or unsubstituted aryloxy groups having 5 to 60 carbon atoms, substituted or unsubstituted arylthio groups having 5 to 60 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms, substituted or unsubstituted burnt (Substituted or unsubstituted C1 to C60 alkyl) amino group, or a substituted or unsubstituted C6 to C60 aryl) amino group, a di (substituted or unsubstituted C6 to C30 aryl group) A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms,

a is an integer of 1 to 4, and when a is 2 or more, R ₃ of 2 or more are the same or different, and when R ₃ is plural, each R ₃ may be in fused form, and n is 1 to 4 It is an integer.

The amine group bonded to A in the formulas (1) and (2) may be represented by any one selected from the group consisting of the following [substituents 1] to [52], but is not limited thereto.

[Substituent 1] [Substituent 2] [Substituent 3]

[Substituent group 4] [Substituent group 5] [Substituent group 6]

 [Substituent group 7] [Substituent group 8] [Substituent group 9]

 [Substituent group 10] [Substituent group 11] [Substituent group 12]

[Substituent group 13] [Substituent group 14] [Substituent group 15]

[Substituent group 16] [Substituent group 17] [Substituent group 18]

[Substituent group 19] [Substituent group 20] [Substituent group 21]

[Substituent group 22] [Substituent group 23] [Substituent group 24]

[Substituent group 25] [Substituent group 26] [Substituent group 27]

[Substituent group 28] [Substituent group 29] [Substituent group 30]

[Substituent group 31] [Substituent group 32] [Substituent group 33]

[Substituent group 34] [Substituent group 35] [Substituent group 36]

[Substituent group 37] [Substituent group 38] [Substituent group 39]

 [Substituent group 40] [Substituent group 41] [Substituent group 42]

[Substituent group 43] [Substituent group 44] [Substituent group 45]

[Substituent group 46] [Substituent group 47] [Substituent group 48]

 [Substituent group 49] [Substituent group 50] [Substituent group 51]

 [Substituent 52]

In the above substituents, R may be the same or different from each other and is independently selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms , A substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, (Substituted or unsubstituted C1-C60 alkyl) amino group, or a substituted or unsubstituted C6-C60 aryl) amino group, a di (substituted or unsubstituted C1-C60 alkyl) amino group, A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, , Each of which may be substituted from 1 to 12, and each substituent may form a condensed ring with adjacent groups.

In the present invention, the host may be a compound represented by the following general formula (1A) to (1D).

≪ EMI ID =

In the above formula (1A)

Wherein Ar _{7 ,} Ar ₈ and Ar ₉ are the same or different and each independently represents a single bond, a substituted or unsubstituted C ₅ -C ₆₀ aromatic linkage, or a substituted or unsubstituted C ₂ -C ₆₀ hetero An aromatic linking group;

R ₂₁ to R ₃₀ are the same or different from each other and each independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group, A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, A substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, A substituted or unsubstituted (alkyl) amino group having 1 to 60 carbon atoms, a di (substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, a substituted or unsubstituted amino group having 6 to 60 carbon atoms, Or an unsubstituted aryl group having 6 to 60 carbon atoms) amino group, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron Each substituent may form a fused ring with the adjacent groups;

E, f and g are the same as or different from each other and each independently 0 or an integer of 1 to 4;

The two sites indicated by * in the anthracene may be the same as or different from each other, and may independently form an anthracene derivative selected from the following formulas (1Aa-1) to (1Aa-3) in combination with the P or Q structure.

[Chemical Formula 1Aa-1] [Chemical Formula 1Aa-2] Chemical Formula 1Aa-3]

The 'substituted' in the 'substituted or unsubstituted' refers to a group selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, An alkyl group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, An aryloxy group having 1 to 24 carbon atoms, an arylsilyl group, and an aryloxy group having 1 to 24 carbon atoms.

 ≪ RTI ID = 0.0 &

In the above formula (1B)

Wherein Ar ₁₇ to Ar ₂₀ are the same or different from each other and each independently represent a substituent group as defined in Ar ₇ to Ar ₈ in Formula 1A, and R ₆₀ to R ₆₃ are the same as defined in R ₂₁ to R ₃₀ in Formula 1A Lt; / RTI >

W and ww are the same as or different from each other, x and xx are the same as or different from each other, w + ww and x + xx are the same or different from each other and independently an integer of 0 to 3; Y and yy are the same or different, and z and zz are the same or different from each other, y + yy to z + zz are not more than 2, and each is an integer of 0 to 2;

[Chemical Formula 1C]

In the above formula (1C)

Wherein Ar ₂₁ to Ar ₂₄ are the same or different from each other and each independently represent a substituent group as defined in Ar ₇ to Ar ₈ of the above formula (1A), and R ₆₄ to R ₆₇ are the same as R ₂₁ To R < ₃₀ >.

The above ee to hh are the same as or different from each other, and each independently is an integer of 1 to 4, and the above-mentioned II to 11 are the same or different and independently an integer of 0 to 4.

[Chemical Formula 1D]

In the above formula (1D)

Wherein Ar ₂₅ to Ar ₂₇ are the same or different from each other and each independently represent a substituent group as defined in Ar ₇ to Ar ₈ in formula (1A), and R ₆₈ to R ₇₃ are the same or different from each other, 1A, the substituents are the same as defined in R ₂₁ to R ₃₀ , and each substituent may form a saturated or unsaturated cyclic structure adjacent to each other. In addition, the mm to ss are the same or different from each other and each independently an integer of 0 to 4.

More specifically, the host may be represented by any one selected from the group consisting of the following [compounds 1] to [56], but is not limited thereto.

[Compound 1] [Compound 2] [Compound 3]

[Compound 4] [Compound 5] [Compound 6]

 [Compound 7] [Compound 8] [Compound 9]

 [Compound 10] [Compound 11] [Compound 12]

 [Compound 13] [Compound 14] [Compound 15]

 [Compound 16] [Compound 17] [Compound 18]

 [Compound 19] [Compound 20] [Compound 21]

 [Compound 22] [Compound 23] [Compound 24]

[Compound 25] [Compound 26] [Compound 27]

 [Compound 28] [Compound 29] [Compound 30]

[Compound 31] [Compound 32] [Compound 33]

 [Compound 34] [Compound 35] [Compound 36]

[Compound 37] [Compound 38] [Compound 39]

[Compound 40] [Compound 41] [Compound 42]

 [Compound 43] [Compound 44] [Compound 45]

 [Compound 46] [Compound 47] [Compound 48]

[Compound 49] [Compound 50] [Compound 51]

 [Compound 52] [Compound 53] [Compound 54]

    [Compound 55] [Compound 56]

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent to those skilled in the art, however, that these examples are provided to further illustrate the present invention, and the scope of the present invention is not limited thereto.

<Examples>

Synthetic Example 1. Synthesis of compound (ETL1)

Synthesis Example 1-1) Synthesis of deutero-substituted 8-hydroxyquinoline

A mixture of 30 g (0.207 mol) of 8-hydroxyquinoline, 101 mL (5.580 mol) of D ₂ O and 1.1 g (0.010 mol) of palladium on carbon to 10 wt% of loading was placed in a sealed high pressure reactor under a nitrogen atmosphere, &Lt; / RTI &gt; for 24 hours. After cooling to room temperature, the resulting solid was filtered, and then subjected to column separation using dichloromethane and hexane to obtain 25 g (yield 80%) of deutero-substituted 8-hydroxyquinoline.

2 shows the 1 H-NMR spectra of the hydrogen-free 8-hydroxyquinoline and the hydrogen-substituted 8-hydroxyquinoline, respectively.

It can be seen that most of the peaks are disappeared by deuterium substitution and 7.1 and 8.8-8.9 ppm, respectively.

The 1 H NMR spectra also show that an average of 2.9 (48%) of the six 8-hydroxyquinoline hydrogens are replaced by deuterium.

MS (MALDI-TOF): m / z 147-115 [M] ⁺

Synthesis Example 1-2) Lithium complex of deutero-substituted 8-hydroxyquinoline ( ETL1 ) Synthesis of

25 g (0.17 mol) of the deutero-substituted 8-hydroxyquinoline prepared in Synthesis Example 1-1 was added to a mixed solution of 4 g (0.17 mol) of lithium hydroxide and 500 ml of dichloromethane. After stirring at room temperature for 24 hours, the reaction is terminated and the resulting crystals are filtered, washed several times with dichloromethane and dried. And dried in vacuo for 2 days to obtain 10 g (yield 38%) of white solid ( ETL1 ).

Synthesis Example 1-3) Lithium complex of deutero-substituted 8-hydroxyquinoline ( ETL1 ) Tablets

10 g (0.064 mol) of the lithium complex ( ETL1 ) dried without further chemical purification is placed in a sublimation apparatus, and the temperature is set at 350 ° C, followed by sublimation purification. This procedure was repeated twice, and then 5 g of a pale yellow solid ( ETL1 ) (yield 50%) was obtained.

Device fabrication and evaluation:

Example  One

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the ITO glass was mounted in a vacuum chamber, the base pressure was adjusted to 1 × 10 ^-7 torr, and then DNTPD (700 Å) and α-NPD (300 Å) were sequentially formed on the ITO. (Formula BE1): ETL1 prepared in Example 1 was mixed at a weight ratio of 1: 1, respectively, to form 300 (weight ratio) A film was formed in the order of LiF (10 Å) and Al (1000 Å). Thus, an organic electroluminescent device was manufactured.

[Chemical Formula BH1] [Chemical Formula BD1] Chemical Formula [BE1]

Example   2

Except that [Formula BH2] was used in place of [Formula BH1] used in Example 1, to prepare an organic electroluminescent device.

 [Chemical Formula BH2]

Example   3

An organic electroluminescent device was fabricated in the same manner and in the same manner as above except that [Formula BD2] was used instead of [Formula BD1] used in Example 1 above.

   (BD2)

Example  4

Except that the [Formula BE2] was used in place of the [Formula BE1] used in Example 1 above to prepare an organic electroluminescent device.

  (BE2)

Comparative Example  One

Instead of deuterium-free Liq (Lithium 8-hydroxy quinolate) corresponding to the electron transport layer material conventionally used in place of ETL1 prepared in Example 1 of the electron transport layer, 1: 1.

    [Liq]

Comparative Example 2

Except that Liq (Lithium 8-hydroxy quinolate) which is not deuterium-substituted, corresponding to the electron transport layer material conventionally used in place of ETL1 in the electron transport layer, was mixed with BE1 in a ratio of 1: 1 Respectively.

Evaluation example

The voltage, current density, luminance, quantum efficiency, color coordinates and lifetime of the organic electroluminescent device manufactured according to Examples 1 to 4 and Comparative Example 1 and Comparative Example 2 were measured and the results are shown in Table 1 ]. T95 in Table 1 means the time required for the luminance to be reduced to 95% of the initial luminance.

As shown in [Table 1], the organic light emitting device using the organometallic compound of the present invention has excellent light emitting properties such as luminance, quantum efficiency and lifetime. In the blue light emitting device, the luminance and the quantum efficiency were increased by about 2 to 5% from the comparative example. From the viewpoint of the life span, [Examples 1 to 4] It is possible to demonstrate the deuterium substitution effect by having an excellent property that the T95 value is increased about twice as compared with the comparative example 1 to the comparative example 2. [

Since the organic electroluminescent device including the organometallic compound according to the present invention can have a relatively high molecular weight as compared with an organometallic compound containing no deuterium due to the presence of deuterium, Melting point and the like can be increased, thereby improving heat resistance and longevity, so that it can be utilized in various display devices.

10: substrate 20: anode
30: Hole injection layer 40: Hole transport layer
50: organic light emitting layer 60: electron transporting layer
70: electron injection layer 80: cathode

Claims (15)

An organometallic compound comprising lithium represented by the following formula (A).
(A)

In the above formula (A)
R ₂ to R ₇ are the same or different from each other and independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted hetero atom, O, N or A substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted silane group, a carbonyl group, a phosphoryl group, an amino group, a nitrile group, a hydroxyl group, a cyano group An amino group, an amino group, an amino group, an amino group, a nitro group, a halogen group, an amide group, and an ester group;
When all of the substituents R ₂ to R ₇ are hydrogen or a substituent other than deuterium, all of the hydrogen atoms contained in the substituents R ₂ to R ₇ may be substituted with deuterium; The substituent R ₂ And R ₇ Lt; / RTI &gt; is deuterium;
The 'substituted' in the above 'substituted or unsubstituted' means a group selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, , An alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms , An alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, Group, and an aryloxy group having 1 to 24 carbon atoms. The method according to claim 1,
R ₂ to R ₇ in the above formula [A] each independently represent hydrogen; heavy hydrogen; A halogen atom; A hydroxyl group; Cyano; A nitro group; An amino group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C2-C20 alkynyl; A substituent of the following formulas (4A) to (4H); &Lt; / RTI &gt;&lt; RTI ID = 0.0 &gt;

In the above general formulas (4A) to (4H)
Z ₁ to Z ₇ are, independently of each other, hydrogen; heavy hydrogen; A halogen atom; A hydroxyl group; Cyano; A nitro group; An amino group; An amidino group; Hydrazine; Hydrazone; A carboxyl group or a salt thereof; Sulfonic acid group or its salt; Phosphoric acid or its salts; An alkyl group having 1 to 10 carbon atoms; An alkoxy group having 1 to 10 carbon atoms; An alkylthio group having 1 to 10 carbon atoms; An alkyl group having 1 to 10 carbon atoms which is substituted with at least one of a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, An alkyl group having 1 to 10 carbon atoms and an alkylthio group having 1 to 10 carbon atoms; A phenyl group; Naphthyl group; A fluorenyl group; A phenanthrenyl group; Anthryl group; Pyrenyl; A crycenyl group; An alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a salt of a carboxyl group or a salt thereof, A phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, and a klycenyl group substituted with at least one of an alkoxy group having 1 to 10 carbon atoms and an alkylthio group having 1 to 10 carbon atoms; Indole diarrhea; A benzimidazolyl group; Carbazolyl group; Imidazolyl group; An imidazolinyl group; Imidazopyridinyl group; already; A pyridinyl group; A pyrimidinyl group; ; Quinoline diazonium; An alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a salt of a carboxyl group or a salt thereof, An imidazolyl group, an imidazolyl group, an imidazopyrimidinyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, A pyridinyl group, a pyrimidinyl group, and a quinolinyl group; Di (alkyl having 1 to 10 carbon atoms) amino group; And an aryl group having 1 to 10 carbon atoms, and the aryl group having 6 to 10 carbon atoms is selected from the group consisting of a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, and a klycenyl group . &Lt; / RTI &gt; 3. The method of claim 2,
The organometallic compound represented by the above formula (A) wherein R ₇ is deuterium The method of claim 3,
The organometallic compound represented by the above formula (A) wherein R ₂ is deuterium The method of claim 3,
At least four of the substituents R ₂ to R ₇ bonded to the aromatic ring of the compound of formula (A) are hydrogen or deuterium; &Lt; RTI ID = 0.0 &gt; 6. The method of claim 5,
The organometallic compound represented by the above formula (A) wherein R ₂ is deuterium The method according to claim 6,
The substituent of R ₂ to R ₇ , which is a substituent of the above-mentioned formula (A), is 0 or 1 substituent which is not hydrogen or deuterium,
When the substituent is 1, the hydrogen or the substituent which is not deuterium is, independently of each other, an alkyl group having 1 to 8 carbon atoms; A cycloalkyl group having 3 to 10 carbon atoms; An aryl group having 6 to 10 carbon atoms; A heteroaryl group having 3 to 8 carbon atoms and having 1 to 2 nitrogen, oxygen, or sulfur atoms; A silyl group having a substituent selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, and an aryl group having 6 to 10 carbon atoms, and the substituents may be deuterium The organometallic compound &lt; RTI ID = 0.0 &gt; The method according to claim 1,
The organometallic compound represented by the above formula (A) is any one selected from the group consisting of the following structural formulas (1) to (81).
Hereinafter, 'D' means deuterium, and '-D / H' means that the substituent bonded to the hydrogen position of each substituent is hydrogen or deuterium.

A first electrode;
A second electrode facing the first electrode; And
And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises at least one organometallic compound selected from the group consisting of the compounds represented by any one of claims 1 to 8. 10. The method of claim 9,
Wherein the organic layer comprises at least one of a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a light emitting layer, an electron transporting layer, and an electron injecting layer. 10. The method of claim 9,
Wherein the organic layer interposed between the first electrode and the second electrode is an electron transporting layer or a light emitting layer. 10. The method of claim 9,
The organic metal compound is included in the electron transport layer,
Wherein the light emitting layer comprises a host and a dopant. 13. The method of claim 12,
Wherein the electron transport layer is a mixture of the organic metal compound and an electron transport compound different from the organic metal compound. 14. The method of claim 13,
Wherein the electron transport layer has a mixing ratio of the organometallic compound and an electron transport compound different from the organometallic compound in a weight ratio of 1:20 to 20: 13. The method of claim 12,
Wherein the dopant is a compound represented by the following Chemical Formula 1 or Chemical Formula 2:
[Chemical Formula 1] &lt; EMI ID =

Among the above-mentioned formulas (1) and (2)
A is a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, an optionally substituted arylene group having 6 to 60 carbon atoms , A substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms having hetero atoms O, N or S;
In the above formula (1)
X ₁ and X ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a single bond; X ₁ and X ₂ may be fused to each other;
Y ₁ and Y ₂ are each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 24 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 24 carbon atoms, a cyano group, a halogen group, a substituted or unsubstituted carbon number of 6 A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron, deuterium, or more is selected, Y ₁ to Y ₂ each are the same or different from each other, and be able to form a condensed ring of aliphatic group, an aromatic, aliphatic or hetero-aromatic heterocyclic group which are adjacent to each other .;
l and m are each an integer of 1 to 20, and n is an integer of 1 to 4;
In the above formula (2)
C _y is substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, and when b is 2 or more, each cycloalkane may be in fused form. Further, the hydrogen sites in the cycloalkane may be substituted with deuterium or alkyl of 1 to 20 carbon atoms, and are the same or different from each other;
B is a single bond or - [C (R ₅ ) (R ₆ )] _p -, and p is an integer of 1 to 3; when p is 2 or more, two or more R ₅ and R ₆ are the same or different;
R ₁ , R ₂ , R _{3 ,} R ₅ and R ₆ are each independently selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, A substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C6- A substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 1 to 60 carbon atoms, Unsubstituted (Substituted or unsubstituted C1-C60 alkyl) amino group, a substituted or unsubstituted C6-C60 arylamino group, a di (substituted or unsubstituted C6- A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms,
a is an integer of 1 to 4, and when a is 2 or more, R ₃ of 2 or more are the same or different, and R ₃ Each R ₃ may be in fused form, and n is an integer from 1 to 4.

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