DE102021108828A1 - Organic electroluminescent device - Google Patents

Abstract

The present disclosure relates to an organic electroluminescent device. The organic electroluminescent device of the present disclosure can have a low voltage, a high efficiency and / or a long life by containing a light emitting layer comprising a specific combination of the compounds and an electron transport zone.

Description

Technical area

The present disclosure relates to an organic electroluminescent device comprising a light emitting layer and an electron transport zone.

State of the art

An electroluminescent (EL) device is a self-light emitting display device that has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time. An organic electroluminescent device (OLED) was first developed by Eastman Kodak in 1987 by using small aromatic diamine molecules and aluminum complexes as materials to form a light emitting layer [ App. Phys. Lett. 51,913,1987 ].

An OLED converts electrical energy into light by applying electricity to an organic electroluminescent material and commonly includes an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer of the OLED may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer (containing host and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, and so on. The materials used in the organic layer can be classified into a hole injection material, a hole transport material, an electron blocking material, a light emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc. according to their function. In such an OLED, by applying an electrical voltage, holes from the anode and electrons from the cathode are injected into a light-emitting layer and excitons with high energy are generated by the recombination of the holes and electrons. As a result of the energy, the organic light-emitting compound changes into an excited state and emits light composed of energy when the organic light-emitting compound returns from the excited state to the ground state.

The most important factor that determines the light output in an OLED are light-emitting materials. The light-emitting materials are required to have the following characteristics: high quantum efficiency, high degree of movement of an electron and a hole, and uniformity and stability of the light-emitting material layer formed. The light emitting material is classified into blue, green, and red light emitting materials according to the light emission color, and further includes yellow or orange light emitting materials. Furthermore, in a functional aspect, the light-emitting material is divided into a host material and a dopant material. Recently, there is an urgent task to develop an OLED with high efficiency and long life. With regard to the EL properties required for medium-sized and large OLED panels, in particular the development of excellent light-emitting material compared to conventional light-emitting materials is urgently required.

An electron transport material in the OLED moves electrons smoothly from the cathode to the light emitting layer and inhibits the movement of holes that could not be combined in the light emitting layer, thereby increasing the chance of recombination between holes and electrons in the light emitting layer. Materials with excellent electron affinity are used as the electron transport material. When used in an OLED because of its high electron affinity, a new electron transport material is required which has fast electron movement properties so that the light-emitting device can exhibit a high luminous efficiency.

In addition, the electron buffer layer is a layer for improving a problem that a decrease in light emission luminance may occur due to a change in current characteristics in a device when exposed to high temperatures in a panel manufacturing process. The properties of a compound contained in the electron buffer layer are important. Further, the compound used in the electron buffer layer plays a role in controlling electron injection according to electron attraction property and electron affinity LUMO (LUMO = Lowest Unoccupied Molecular Orbital). As a result, it can play a role in improving the efficiency and lifespan of the OLED.

Korean Patent Application Laid-Open No. 2019-0042791 A and Korean Patent Application Laid-Open No. 2017-0130434 A disclose an OLED in which an anthracene-based host is combined with a dopant having a molecular structure connecting a heteroatom and an aromatic ring. However, the references do not specifically disclose an OLED that contains a combination of organic electroluminescent compounds specified here.

Disclosure of the invention

Technical task

The object of the present disclosure is to provide an organic electroluminescent device which has a low voltage, a high efficiency and / or a long life by containing a light emitting layer comprising a specific combination of the compounds and an electron transport zone.

Solution of the task

Dabei gilt, dass in Formel 1
L₁ und L₂ jeweils unabhängig für eine Einfachbindung, ein substituiertes oder unsubstituiertes (C6-C30)-Arylen oder ein substituiertes oder unsubstituiertes (5- bis 30-gliedriges) Heteroarylen stehen;
Ar₁ und Ar₂ jeweils unabhängig für ein substituiertes oder unsubstituiertes (C6-C30)-Aryl oder ein substituiertes oder unsubstituiertes (5- bis 30-gliedriges) Heteroaryl stehen; und
R₁ bis R₈ jeweils unabhängig für Wasserstoff, Deuterium, Halogen, Cyano, ein substituiertes oder unsubstituiertes (C1-C30)-Alkyl, ein substituiertes oder unsubstituiertes (C6-C30)-Aryl, ein substituiertes oder unsubstituiertes (3- bis 30-gliedriges) Heteroaryl, ein substituiertes oder unsubstituiertes (C3-C30)-Cycloalkyl, ein substituiertes oder unsubstituiertes (C1-C30)-Alkoxy, ein substituiertes oder unsubstituiertes Tri-(C1-C30)-alkylsilyl, ein substituiertes oder unsubstituiertes Di-(C1-C30)-alkyl-(C6-C30)-arylsilyl, ein substituiertes oder unsubstituiertes (C1-C30)-Alkyldi-(C6-C30)-arylsilyl, ein substituiertes oder unsubstituiertes Tri-(C6-C30)-arylsilyl oder -L₄-N(Ar₄)(Ar₅) stehen;

wobei in Formel 2
Ring A, Ring B und Ring C jeweils unabhängig für ein substituiertes oder unsubstituiertes (C6-C30)-Aryl oder ein substituiertes oder unsubstituiertes (3- bis 50-gliedriges)Heteroaryl stehen;
Y₁ für B steht;
X₁ und X₂ jeweils unabhängig für NR stehen; und
R für Wasserstoff, Deuterium, Halogen, Cyano, ein substituiertes oder unsubstituiertes (C1-C30)-Alkyl, ein substituiertes oder unsubstituiertes (C6-C30)-Aryl, ein substituiertes oder unsubstituiertes (3- bis 30-gliedriges) Heteroaryl, ein substituiertes oder unsubstituiertes (C3-C30)-Cycloalkyl, ein substituiertes oder unsubstituiertes (C1-C30)-Alkoxy, ein substituiertes oder unsubstituiertes Tri-(C1-C30)-alkylsilyl, ein substituiertes oder unsubstituiertes Di-(C1-C30)-alkyl-(C6-C30)-arylsilyl, ein substituiertes oder unsubstituiertes (C1-C30)-Alkyldi-(C6-C30)-arylsilyl, ein substituiertes oder unsubstituiertes Tri-(C6-C30)-arylsilyl oder -L₄-N(Ar₄)(Ar_s) steht oder mit mindestens einem von Ring A, Ring B und Ring C zu einem oder mehreren Ringen verknüpft sein kann;

wobei in Formel 11
Z₁ bis Z₃ jeweils unabhängig für CR₁₈ stehen;
R₁₈ jeweils unabhängig für Wasserstoff, Deuterium, Halogen, Cyano, ein substituiertes oder unsubstituiertes (C1-C30)-Alkyl, ein substituiertes oder unsubstituiertes (C6-C50)-Aryl, ein substituiertes oder unsubstituiertes (3- bis 50-gliedriges) Heteroaryl, ein substituiertes oder unsubstituiertes (C3-C30)-Cycloalkyl, ein substituiertes oder unsubstituiertes (3- bis 7-gliedriges) Heterocycloalkyl, ein substituiertes oder unsubstituiertes (C1-C30)-Alkoxy, ein substituiertes oder unsubstituiertes Tri-(C1-C30)-alkylsilyl, ein substituiertes oder unsubstituiertes Di-(C1-C30)-alkyl-(C6-C30)-arylsilyl, ein substituiertes oder unsubstituiertes (C1-C30)-Alkyldi-(C6-C30)-arylsilyl, ein substituiertes oder unsubstituiertes Tri-(C6-C30)-arylsilyl oder -L₄-N(Ar₄)(Ar₅) steht, mit der Maßgabe, dass R₁₈ 2-Dimethylfluorenyl, Chinolinyl und Pyridyl nicht einschließt;
L₄ jeweils unabhängig für eine Einfachbindung, ein substituiertes oder unsubstituiertes (C6-C30)-Arylen oder ein substituiertes oder unsubstituiertes (3- bis 30-gliedriges) Heteroarylen steht;
Ar₄ und Ar₅ jeweils unabhängig für Wasserstoff, ein substituiertes oder unsubstituiertes (C1-C30)-Alkyl, ein substituiertes oder unsubstituiertes (C2-C30)-Alkenyl, einen substituierten oder unsubstituierten anellierten Ring aus einem aliphatischen (C3-C30)-Ring und einem aromatischen (C6-C30)-Ring, ein substituiertes oder unsubstituiertes (C6-C30)-Aryl oder ein substituiertes oder unsubstituiertes (3- bis 30-gliedriges) Heteroaryl stehen; und
dann, wenn mehrere durch das gleiche Symbol wiedergegebene Substituenten vorliegen, jeder der durch das gleiche Symbol wiedergegebenen Substituenten gleich oder verschieden sein kann.As a result of intensive studies to achieve the above technical problem, the present invention has found that the above object can be achieved by an organic electroluminescent device comprising a first electrode; a second electrode facing the first electrode; a light-emitting layer between the first electrode and the second electrode and an electron transport zone between the light-emitting layer and the second electrode, wherein the electron transport zone contains a hole blocking layer and / or an electron buffer layer and an electron transport layer and an electron injection layer, the electron transport layer between the hole blocking layer or the Electron buffer layer and the second electrode is formed, wherein the electron injection layer is formed between the electron transport layer and the second electrode, wherein the light-emitting layer comprises a compound represented by the following formula 1 and a compound represented by the following formula 2, and wherein the hole blocking layer and / or the electron buffer layer comprising a compound represented by the following formula 11 can be achieved, so that the present invention has been completed.

It applies that in Formula 1
L ₁ and L ₂ each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5- to 30-membered) heteroarylene;
Ar ₁ and Ar ₂ each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5- to 30-membered) heteroaryl; and
R ₁ to R ₈ each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl, a substituted or unsubstituted (3- to 30- membered) heteroaryl, a substituted or unsubstituted (C3-C30) -cycloalkyl, a substituted or unsubstituted (C1-C30) -alkoxy, a substituted or unsubstituted tri- (C1-C30) -alkylsilyl, a substituted or unsubstituted di- (C1 -C30) -alkyl- (C6-C30) -arylsilyl, a substituted or unsubstituted (C1-C30) -alkyldi (C6-C30) -arylsilyl, a substituted or unsubstituted tri- (C6-C30) -arylsilyl or -L ₄ -N (Ar ₄ ) (Ar ₅ );

where in formula 2
Ring A, Ring B and Ring C each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3- to 50-membered) heteroaryl;
Y _{1 represents} B;
X ₁ and X ₂ each independently represent NR; and
R represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl, a substituted or unsubstituted (3 to 30-membered) heteroaryl, a substituted one or unsubstituted (C3-C30) -cycloalkyl, a substituted or unsubstituted (C1-C30) -alkoxy, a substituted or unsubstituted tri- (C1-C30) -alkylsilyl, a substituted or unsubstituted di- (C1-C30) -alkyl- (C6-C30) -arylsilyl, a substituted or unsubstituted (C1-C30) -alkyldi (C6-C30) -arylsilyl, a substituted or unsubstituted tri- (C6-C30) -arylsilyl or -L ₄ -N (Ar ₄ ) (Ar _s ) or can be linked to at least one of ring A, ring B and ring C to form one or more rings;

where in formula 11
Z ₁ to Z ₃ each independently represent CR ₁₈ ;
R ₁₈ each independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C50) -aryl, a substituted or unsubstituted (3 to 50-membered) heteroaryl , a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, a substituted or unsubstituted (C1-C30) -alkoxy, a substituted or unsubstituted tri- (C1-C30) -alkylsilyl, a substituted or unsubstituted di- (C1-C30) -alkyl- (C6-C30) -arylsilyl, a substituted or unsubstituted (C1-C30) -alkyldi- (C6-C30) -arylsilyl, a substituted or unsubstituted tri - (C6-C30) -arylsilyl or -L ₄ -N (Ar ₄ ) (Ar ₅ ) with the proviso that R ₁₈ does not include 2-dimethylfluorenyl, quinolinyl and pyridyl;
L ₄ each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene;
Ar ₄ and Ar ₅ each independently represent hydrogen, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C2-C30) -alkenyl, a substituted or unsubstituted fused ring from an aliphatic (C3-C30) ring and an aromatic (C6-C30) ring, a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3 to 30-membered) heteroaryl; and
when there are plural substituents represented by the same symbol, each of the substituents represented by the same symbol may be the same or different.

Advantageous Effects of the Invention

According to the present disclosure, there is provided an organic electroluminescent device of low voltage, high efficiency, and / or long life, and a display device or lighting device can be manufactured using the same.

Embodiment of the invention

The following describes the present disclosure in detail. However, the following description is intended to illustrate the invention and in no way limit the scope of the invention.

As used herein, “organic electroluminescent material” means a material that can be used in an organic electroluminescent device and that can comprise at least one compound. The organic electroluminescent material can, as required, be contained in any layer from which an organic electroluminescent device is constructed. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light emitting auxiliary material, an electron blocking material, a light emitting material (containing host and dopant materials), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, and so on . Act.

The organic electroluminescent device of the present disclosure includes a first electrode; a second electrode facing the first electrode; a light emitting layer between the first electrode and the second electrode and may include a hole transport zone between the first electrode and the light emitting layer and may include an electron transport zone between the light emitting layer and the second electrode. One of the first electrode and the second electrode can be an anode and the other can be a cathode.

The hole transport zone refers to a zone in which holes move between the first electrode and the light-emitting layer. The hole transport zone can contain, for example, a hole injection layer, a hole transport layer, an auxiliary hole layer, a light-emitting auxiliary layer and / or an electron blocking layer. The hole injection layer, the hole transport layer, the hole auxiliary layer, the light-emitting auxiliary layer and the electron blocking layer can each be a single layer or a plurality of layers, with two or more layers being stacked.

In addition, the hole transport zone can contain a p-doped hole injection layer, a hole transport layer and a light-emitting auxiliary layer. Here, the p-doped hole injection layer is to be understood as a hole injection layer blocked with a p-dopant. The p-type dopant is a material that has p-type semiconductor properties. The p-semiconductor property refers to the properties of the injection or the transport of holes at the HOMO energy level (HOMO = Highest Occupied Molecule Orbital), i.e. the property of a material with high hole conductivity.

The light-emitting layer is a layer from which light is emitted, and may be single-layer or multilayer with stacking of two or more layers. In the light-emitting layer, the doping concentration of the dopant compound, based on the host compound, can preferably be less than 20% by weight.

The electron transport zone is to be understood as a zone in which electrons move between the light-emitting layer and the second electrode. For example, the electron transport zone can contain a hole blocking layer, an electron transport layer, an electron buffer layer and / or an electron injection layer. The hole blocking layer, the electron transport layer, the electron buffer layer, and the electron injection layer may each be a single layer or multiple layers with two or more layers stacked.

According to an embodiment of the present disclosure, the light emitting layer comprises a compound represented by Formula 1 above and a compound represented by Formula 2 above. The electron transport zone can contain a hole blocking layer and / or an electron buffer layer and an electron transport layer and an electron injection layer. The compound represented by the above formula 11 is contained in the hole blocking layer and / or the electron buffer layer. The hole blocking layer and / or the electron buffer layer are / is formed between the light emitting layer and the second electrode. The electron transport layer is formed between the hole blocking layer or the electron buffer layer and the second electrode, and the electron injection layer is formed between the electron transport layer and the second electrode.

The following describes the compounds represented by the above formulas 1, 2 and 11 in more detail.

The term “(C1-C30) -alkyl” here means a linear or branched alkyl having 1 to 30 carbon atoms from which the chain is built up, the number of carbon atoms preferably being 1 to 20 and more preferably 1 to 10. The above alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl, and so on. The term “(C2-C30) -alkenyl” here means a linear or branched alkenyl having 2 to 30 carbon atoms from which the chain is built up, the number of carbon atoms preferably being 2 to 20 and more preferably 2 to 10. The above alkenyl may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, and so on. The term “(C2-C30) -alkynyl” here means a linear or branched alkynyl having 2 to 30 carbon atoms from which the chain is built up, the number of carbon atoms preferably being 2 to 20 and more preferably 2 to 10. The above alkynyl may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, and so on. The term “(C3-C30) -cycloalkyl” here means a mono- or polycyclic hydrocarbon with 3 to 30 ring skeleton carbon atoms, the number of carbon atoms preferably being 3 to 20 and more preferably 3 to 7. The above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and so on. Here the term "(3- to 7-membered) heterocycloalkyl" is a cycloalkyl with 3 to 7 ring skeleton atoms, preferably 5 to 7 ring skeleton atoms, and at least one heteroatom from the group consisting of B, N, O, S, Si and P, preferably O, S and N, and includes tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and so on. Here the term "(C6-C30) -aryl (en) or (C6-C50) -aryl (en)" is a monocyclic or fused ring radical, which is derived from an aromatic hydrocarbon with 6 to 30 or 6 to 50 ring skeleton Derives carbon atoms, wherein the number of ring skeleton carbon atoms is preferably 6 to 25 and more preferably 6 to 18, and may be partially saturated. The aryl can comprise a spiro structure. Specific examples of the aryl are phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, naphthyl, triphenyl, tetdenra-nyl, pyrenyl, triphenyl, tetdenra-nyl, pyrenacylene, tetra-naphthylene, pyrenacylene, phenylnaphthyl, phenylnaphthyl, triphenyl, tetra-naphthyl, pyrenyl, tetra-naphthyl , Fluoranthenyl, spirobifluorenyl, azulenyl, etc. More specifically, the aryl can be phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3- Phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo [c] phenanthryl, benzo [g] chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo [a] fluorenyl, benzo [b] fluorenyl, benzo [ c] fluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, o-terphenyl, m-terphenyl-4-yl, m-Terphenyl-3-yl, m-Terphenyl-2-yl, p-Terphenyl-4-yl, p-Terphenyl-3-yl, p-Terphenyl-2-yl, m-Quaterphenyl, 3-Fluoranthenyl, 4- Fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m- Cumenyl, p-cumenyl, p-tert-butylphenyl, p- (2-phenylpropyl) phenyl, 4'-methylbiphenylyl, 4 "-tert-butyl-p-terphenyl-4-yl, 9,9-dimethyl-1-fluorenyl , 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl , 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 11,11-dimethyl-1-benzo [a] fluorenyl, 11,11-dimethyl-2-benzo [a] fluorenyl, 11 , 11-dimethyl-3-benzo [a] fluorenyl, 11,11-dimethyl-4-benzo [a] fluorenyl, 11,11-dimethyl-5-benzo [a] fluorenyl, 11,11-dimethyl-6-benzo [a] fluorenyl, 11,11-dimethyl-7-benzo [a] fluorenyl, 11,11-dimethyl-8-benzo [a] fluorenyl, 11,11-dimethyl-9-benzo [a] fluorenyl, 11.11 -Dimethyl-10-benzo [a] fluorenyl, 11,11-dimethyl-1-benzo [b] fluorenyl, 11,11-dimethyl-2-benzo [b] fluorenyl, 11,11-dimethyl-3-benzo [b] fluorenyl, 11,11-dimethyl-4-benzo [b] fluorenyl, 11,11-dimethyl-5- benzo [b] fluorenyl, 11,11-dimethyl-6-benzo [b] fluorenyl, 11,11-dimethyl-7-benzo [b] fluorenyl, 11,11-dimethyl-8-benzo [b] fluorenyl, 11, 11-dimethyl-9-benzo [b] fluorenyl, 11,11-dimethyl-10-benzo [b] fluorenyl, 11,11-dimethyl-1-benzo [c] fluorenyl, 11,11-dimethyl-2-benzo [ c] fluorenyl, 11,11-dimethyl-3-benzo [c] fluorenyl, 11,11-dimethyl-4-benzo [c] fluorenyl, 11,11-dimethyl-5-benzo [c] fluorenyl, 11,11- Dimethyl-6-benzo [c] fluorenyl, 11,11-dimethyl-7-benzo [c] fluorenyl, 11,11-dimethyl-8-benzo [c] fluorenyl, 11,11-dimethyl-9-benzo [c] fluorenyl, 11,11-dimethyl-10-benzo [c] fluorenyl, 11,11-diphenyl-1-benzo [a] fluorenyl, 11,11-diphenyl-2-benzo [a] fluorenyl, 11,11-diphenyl- 3-benzo [a] fluorenyl, 11,11-diphenyl-4-benzo [a] fluorenyl, 11,11-diphenyl-5-benzo [a] fluorenyl, 11,11-diphenyl-6-benzo [a] fluorenyl, 11,11-diphenyl-7-benzo [a] fluorenyl, 11,11-diphenyl-8-benzo [a] fluorenyl, 11,11-diphenyl-9-benzo [a] f luorenyl, 11,11-diphenyl-10-benzo [a] fluorenyl, 11,11-diphenyl-1-benzo [b] fluorenyl, 11,11-diphenyl-2-benzo [b] fluorenyl, 11,11-diphenyl- 3-benzo [b] fluorenyl, 11,11-diphenyl-4-benzo [b] fluorenyl, 11,11-diphenyl-5-benzo [b] fluorenyl, 11,11-diphenyl-6-benzo [b] fluorenyl, 11,11-diphenyl-7-benzo [b] fluorenyl, 11,11-diphenyl-8-benzo [b] fluorenyl, 11,11-diphenyl-9-benzo [b] fluorenyl, 11,11-diphenyl-10- benzo [b] fluorenyl, 11,11-diphenyl-1-benzo [c] fluorenyl, 11,11-diphenyl-2-benzo [c] fluorenyl, 11,11-diphenyl-3-benzo [c] fluorenyl, 11, 11-diphenyl-4-benzo [c] fluorenyl, 11,11-diphenyl-5-benzo [c] fluorenyl, 11,11-diphenyl-6-benzo [c] fluorenyl, 11,11-diphenyl-7-benzo [ c] fluorenyl, 11,11-diphenyl-8-benzo [c] fluorenyl, 11,11-diphenyl-9-benzo [c] fluorenyl, 11,11-diphenyl-10-benzo [c] fluorenyl, and so on. Here the term “(3 to 30-membered) heteroaryl (en) or (3 to 50-membered) heteroaryl (en)” is an aryl with 3 to 30 or 3 to 50 ring skeleton atoms, the number of ring skeleton atoms being preferred 3 to 30 and more preferably 5 to 20, and with at least one and preferably 1 to 4 heteroatoms from the group consisting of B, N, O, S, Si, P, Se and Ge. The above heteroaryl or heteroarylene can be a monocyclic ring or a fused ring which is condensed with at least one benzene ring, and be partially saturated. In addition, the above heteroaryl or heteroarylene here can be a heteroaryl formed by linking at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds and comprise a spiro structure. Examples of the heteroaryl may specifically be monocyclic ring type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, pyrazolrazolyl, tetrazinyl, pyrazolrazyl, pyrimidinyl, pyridazinyl, etc. and a heteroaryl fused ring type including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, Naphthobenzofuranyl, Naphthobenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, Benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl , Cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthiridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, etc. More specifically, the heteroaryl can be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5- Indolidinyl, 6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridinyl, 4-pyridyl, 1-indolyl 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7- Isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl lyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl-1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl, Azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1- Acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3- Methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3- (2-phenylpropyl) pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1 -indolyl, 2-met hyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl 3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphuranyl-zofuranyben, 2-naphtho- [1,2-b] -benzofuranyl, 3-naphtho- [1,2-b] -benzofuranyl, 4-naphtho- [1,2-b] -benzofuranyl, 5-naphtho- [1,2 -b] -benzofuranyl, 6-naphtho- [1,2-b] -benzofuranyl, 7-naphtho- [1,2-b] -benzofuranyl, 8-naphtho- [1,2-b] -benzofuranyl, 9- Naphtho [1,2-b] benzofuranyl, 10-naphtho [1,2-b] benzofuranyl, 1-naphtho [2,3-b] benzofuranyl, 2-naphtho [2,3-b ] -benzofuranyl, 3-naphtho- [2,3-b] -benzofuranyl, 4-naphtho- [2,3-b] -benzofuranyl, 5-naphtho- [2,3-b] -benzofuranyl, 6-naphtho- [2,3-b] -benzofuranyl, 7-naphtho- [2,3-b] -benzofuranyl, 8-naphtho- [2,3-b] -benzofuranyl, 9-naphtho- [2,3-b] - benzofuranyl, 10-naphtho- [2,3-b] -benzofuranyl, 1-naphtho- [2,1-b] -benzofuranyl, 2-naphtho- [2,1-b] -benzofuranyl, 3-napht ho- [2,1-b] -benzofuranyl, 4-naphtho- [2,1-b] -benzofuranyl, 5-naphtho- [2,1-b] -benzofuranyl, 6-naphtho- [2,1-b ] -benzofuranyl, 7-naphtho- [2,1-b] -benzofuranyl, 8-naphtho- [2,1-b] -benzofuranyl, 9-naphtho- [2,1-b] -benzofuranyl, 10-naphtho- [2,1-b] -benzofuranyl, 1-naphtho- [1,2-b] -benzothiophenyl, 2-naphtho- [1,2-b] -benzothiophenyl, 3-naphtho- [1,2-b] - benzothiophenyl, 4-naphtho- [1,2-b] -benzothiophenyl, 5-naphtho- [1,2-b] -benzothiophenyl, 6-naphtho- [1,2-b] -benzothiophenyl, 7-naphtho- [1 , 2-b] -benzothiophenyl, 8-naphtho- [1,2-b] -benzothiophenyl, 9-naphtho- [1,2-b] -benzothiophenyl, 10-naphtho- [1,2-b] -benzothiophenyl, 1-naphtho- [2,3-b] -benzothiophenyl, 2-naphtho- [2,3-b] -benzothiophenyl, 3-naphtho- [2,3-b] -benzothiophenyl, 4-naphtho- [2,3 -b] -benzothiophenyl, 5-naphtho- [2,3-b] -benzothiophenyl, 1-naphtho- [2,1-b] -benzothiophenyl, 2-naphtho- [2,1-b] -benzothiophenyl, 3- Naphtho- [2,1-b] -benzothiophenyl, 4-naphtho- [2,1-b] -benzothiophenyl, 5-naphtho- [2,1-b] -benzothiophenyl, 6-naphtho- [2,1-b ] benzothiophenyl, 7-naphtho- [2.1 -b] -benzothiophenyl, 8-naphtho- [2,1-b] -benzothiophenyl, 9-naphtho- [2,1-b] -benzothiophenyl, 10-naphtho- [2,1-b] -benzothiophenyl, 1- Include silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, etc. Here the term "a fused ring made of an aliphatic (C3-C30) - Ring and an aromatic (C6-C30) ring by fusing at least one aliphatic ring with 3 to 30 ring skeleton carbon atoms, the number of carbon atoms preferably being 3 to 25 and more preferably 3 to 18, and at least one aromatic ring with 6 to 30 ring skeleton carbon atoms, the number of carbon atoms being preferably 6 to 25 and more preferably 6 to 18, formed ring. For example, the fused ring can be a fused ring made of at least one benzene and at least one cyclohexane, or a fused ring made of at least one naphthalene and at least one cyclopentane, and so on. Here, the carbon atoms in the fused ring can be selected from an aliphatic (C3-C30) ring and an aromatic (C6-C30) ring through at least one heteroatom selected from B, N, O, S, Si and P, preferably at least one heteroatom selected from N, O and S may be replaced. Here the term “halogen” includes F, CI, Br and I.

In addition, “ortho (o)”, “meta (m)” and “para (p)” should designate the substitution position of all substituents. An ortho position is a compound having substituents that are adjacent to one another, e.g. B. at positions 1 and 2 of benzene. A meta position is the next substitution position of the immediately adjacent substitution position, e.g. B. a compound having substituents in positions 1 and 3 on benzene. A para position is the next substitution position of the meta position, e.g. B. a compound with substituents in positions 1 and 4 on benzene.

In addition, “substituted” in the term “substituted or unsubstituted” means that a hydrogen atom in a particular functional group has been replaced by another atom or a functional group; H. a substituent. In the case of the substituents of substituted alkyl, substituted alkenyl, substituted aryl, substituted aryl, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted alkoxy, substituted heterocycloalkyl, substituted arylsilylsilylsilylsilylsilylsilylsilylsilylsilylsilylsilylsilylsilylsilyls, substituted dialkylsilylsilyls, substituted alkyldiarylsylsilyls, substituted alkyldiarylsylsilyls , the substituted triarylsilyl and the substituted fused ring of an aliphatic ring and an aromatic ring in the formulas of the present disclosure are each independently at least one selected from the group consisting of deuterium; Halogen; Cyano; Carboxyl; Nitro; Hydroxy; (C1-C30) alkyl; Halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3- to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (5- to 50-membered) heteroaryl which is unsubstituted or substituted by (C1-C30) -alkyl, (C6-C30) -aryl and / or di- (C6-C30) -arylamino; (C6-C30) -aryl which is unsubstituted or substituted by (C1-C30) -alkyl, (3- to 50-membered) heteroaryl and / or mono- or di- (C6-C30) -arylamino; Tri- (C1-C30) alkylsilyl; Tri- (C6-C30) arylsilyl; Di- (C1-C30) -alkyl- (C6-C30) -arylsilyl; (C1-C30) -alkyldi (C6-C30) -arylsilyl; Amino; Mono- or di- (C1-C30) -alkylamino; Mono- or di- (C2-C30) -alkenylamino; Mono- or di- (C6-C30) -arylamino which is unsubstituted or substituted by (C1-C30) -alkyl, (5- to 30-membered) heteroaryl and / or di- (C6-C30) -arylamino; Mono- or di- (3- to 30-membered) heteroarylamino; (C1-C30) -alkyl- (C2-C30) -alkenylamino; (C1-C30) -alkyl- (C6-C30) -arylamino; (C1-C30) -alkyl- (3- to 30-membered) heteroarylamino; (C2-C30) -alkenyl- (C6-C30) -arylamino; (C2-C30) -alkenyl- (3- to 30-membered) heteroarylamino; (C6-C30) aryl (3 to 30 membered) heteroarylamino; (C1-C30) -alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; Di (C6-C30) arylboronyl; Di (C1-C30) alkylboronyl; (C1-C30) -alkyl- (C6-C30) -arylboronyl; (C6-C30) -Ar- (C1-C30) -alkyl and (C1-C30) -alkyl- (C6-C30) -aryl. According to one embodiment of the present disclosure, the substituents each independently represent at least one from the group consisting of deuterium; (C1-C20) alkyl; (5- to 40-membered) heteroaryl which is unsubstituted or substituted by deuterium, (C1-C20) -alkyl and / or (C6-C25) -aryl; (C6-C25) -aryl which is unsubstituted or substituted by deuterium, (C1-C20) -alkyl, (3- to 30-membered) heteroaryl and / or di- (C6-C25) -arylamino; and mono- or di- (C6-C25) -alkylamino which is unsubstituted or substituted by deuterium, (C1-C20) -alkyl, (5- to 25-membered) heteroaryl and / or di- (C6-C25) -arylamino is. For example, the substituents can be at least one of deuterium; Methyl; tert-butyl; Phenyl which is unsubstituted or substituted by methyl, pyridinyl, carbazolyl, dibenzofuranyl, diphenylamino, phenoxazinyl, phenothiazinyl and / or acridinyl which is substituted by methyl; Naphthyl; Biphenyl; Terphenyl; Triphenylenyl; Dimethylfluorenyl; Phenylfluorenyl; Diphenylfluorenyl; Phenanthrenyl; Pyridinyl; Triazinyl which is substituted by phenyl and / or naphthyl; Indolyl which is substituted by diphenyl; Benzoimidazolyl which is substituted by phenyl; Quinolyl; Isoquinolyl; Quinazolinyl substituted by phenyl; Carbazolyl which is unsubstituted or substituted by phenyl; Dibenzofuranyl; Dibenzothiophenyl; Benzocarbazolyl which is unsubstituted or substituted by phenyl; Dibenzocarbazolyl; Benzophenanthrothiophenyl; Phenoxazinyl; Phenothiazinyl; Acridinyl which is substituted by at least one methyl; Xanthenyl which is substituted by at least one methyl; Diphenylamino which is unsubstituted or substituted by methyl and / or diphenylamino; Dimethylfluorenylphenylamino; Phenylnaphthylamino and phenylamino which is substituted by phenylcarbazolyl or dibenzofuranyl; Triphenylsilyl or a substituted or unsubstituted (16- to 33-membered) heteroaryl containing at least one of N, O and S, act.

Here, the term “a ring formed when linked to an adjacent substituent” in the formulas of the present disclosure means a substituted or unsubstituted (3 to 30-membered) mono- or polycyclic, alicyclic, aromatic ring or a combination thereof. Furthermore, the ring formed can contain at least one heteroatom from the group consisting of B, N, O, S, Si and P, preferably at least one heteroatom from the group consisting of N, O and S. According to one embodiment of the present disclosure, the number of atoms in the ring skeleton is 5 to 20; According to another embodiment of the present disclosure, the number of atoms in the ring skeleton is 5-15.

In the formulas of the present disclosure, heteroaryl, heteroarylene and heterocycloalkyl can each independently contain at least one heteroatom selected from the group consisting of B, N, O, S, Si and P. Furthermore, the above heteroatom with at least one substituent from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl, a substituted or unsubstituted (5- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30) -cycloalkyl, a substituted or unsubstituted (C1-C30) -alkoxy, a substituted or unsubstituted tri- (C1-C30) -alkylsilyl, a substituted one or unsubstituted di- (C1-C30) -alkyl- (C6-C30) -arylsilyl, a substituted or unsubstituted (C1-C30) -alkyldi (C6-C30) -arylsilyl, a substituted or unsubstituted tri- (C6-C30 ) -arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30) -alkylamino, a substituted or unsubstituted mono- or di- (C6-C30) -arylamino and a substituted or unsubstituted (C1-C30) -alkyl (C6-C30) -arylamino linked se in.

In the formulas of the present disclosure, when there are plural substituents represented by the same symbol, each of the substituents represented by the same symbol may be the same or different.

The light-emitting material according to one embodiment comprises at least one anthracene derivative represented by Formula 1 above. In one embodiment, the compound represented by Formula 1 above can be a fluorescent host, such as a fluorescent host for emitting blue light.

In formula 1 above, L ₁ and L ₂ each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (5- to 30-membered) heteroarylene. Preferably, L ₁ and L _{2 can} each independently be a single bond, a substituted or unsubstituted (C6-C25) arylene or a substituted or unsubstituted (5- to 25-membered) heteroarylene, more preferably a single bond, a substituted or unsubstituted (C6- C18) -arylene or a substituted or unsubstituted (5- to 18-membered) heteroarylene.

In one embodiment, L ₁ and L _{2 can} each independently represent a single bond or be selected from the substituents listed in Group 1 below.

In group 1, Z can represent O, S, NR ₁₀₁ , CR ₁₀₂ R ₁₀₃ or SiR ₁₀₄ R ₁₀₅ , preferably O, S or NR ₁₀₁ .

In group 1, R ₁₀₁ to R ₁₀₅ each independently represent a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl or can be linked to the adjacent substituent to form one or more rings; can preferably each independently be a substituted or unsubstituted (C1-C10) -alkyl, a substituted or unsubstituted (C6-C25) -aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl and can more preferably each independently be a substituted one or unsubstituted (C1-C4) -alkyl, a substituted or unsubstituted (C6-C18) -aryl or a substituted or unsubstituted (5- to 18-membered) heteroaryl. For example, R ₁₀₁ can be phenyl.

In each remainder of group 1, each of the two * stands for a binding site to the anthracene skeleton and a binding site to Ar ₁ or Ar ₂ .

In one embodiment, L ₁ and L _{2 can} each independently be a single bond, phenylene, naphthylene, biphenylene, phenanthrenylene, benzofluorenylene substituted by at least one methyl, dibenzofuranylene, and so on.

In formula 1 above, Ar ₁ and Ar _{2 can} each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5- to 30-membered) heteroaryl and can preferably be a substituted or unsubstituted (C6-C25 ) -Aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C25) -aryl or a substituted or unsubstituted (5- to 20-membered) heteroaryl.

In one embodiment, Ar ₁ and Ar _{2 can} each be independently selected from the substituents listed in Group 2 below.

In Group 2, A, G, E and M each independently represent O, S, NR ₁₀₆ , CR ₁₀₇ R ₁₀₈ or SiR ₁₀₉ R ₁₁₀ . For example, AO or CR _{107 can be} R ₁₀₈ , EO or S, and any of G and MO, S or NR ₁₀₆ .

R ₁₀₆ to R ₁₁₀ each independently represent a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl or can be mixed with the adjacent substituents can be linked to form one or more rings; can preferably each be independently (C1-C10) -alkyl, a substituted or unsubstituted (C6-C25) -aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl and can more preferably each be independently unsubstituted (C1-C4) -Alkyl, unsubstituted (C6-C18) -aryl or unsubstituted (5- to 18-membered) heteroaryl. For example, R ₁₀₆ through R _{110 can} each independently be unsubstituted methyl, unsubstituted naphthyl, or unsubstituted phenyl.

In group 2, * stands for a binding site to the anthracene skeleton, L ₁ or L ₂ .

In one embodiment, Ar ₁ and Ar _{2 can} each independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted terphenyl substituted or unsubstituted triphenylenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted epoxyphenanthrenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted furanofluorenyl, a substituted or unsubstituted indenofluorenyl unsubstituted benzofuranyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted benzonaphthofuranyl, a substituted or unsubstituted one Dinaphthofuranyl, a substituted or unsubstituted Anthrabenzofuranyl, a substituted or unsubstituted Chrysenofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted Benzonaphthothiophenyl, a substituted or unsubstituted Benzocarbazolyl, a substituted or unsubstituted Benzofurocarbazolyl, a substituted or unsubstituted Benzothienocarbazolyl, a substituted or unsubstituted Benzobisbenzofuranyl, a substituted or unsubstituted oxathiaindenofluorenyl, a substituted or unsubstituted dibenzocarbazolyl, a substituted or unsubstituted benzobisbenzothiophenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted indolocarbazolyl, an unsubstituted or unsubstituted or unsubstituted benzothiazole, unsubstituted or unsubstituted, benzothiazol, or unsubstituted, or unsubstituted, phenolocarbazolanthazole, or unsubstituted or unsubstituted benzothiazole, or unsubstituted, or unsubstituted, benzothiazole, or unsubstituted, or unsubstituted, benzothiazol-substituted, or unsubstituted, or act uated or unsubstituted naphthothiazolyl.

In Formula 1 above, R ₁ to R ₈ each independently represent Hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted one (C3-C30) -cycloalkyl, a substituted or unsubstituted (C1-C30) -alkoxy, a substituted or unsubstituted tri- (C1-C30) -alkylsilyl, a substituted or unsubstituted di- (C1-C30) -alkyl- (C6 -C30) -arylsilyl, a substituted or unsubstituted (C1-C30) -alkyldi (C6-C30) -arylsilyl, a substituted or unsubstituted tri- (C6-C30) -arylsilyl or -L ₄ -N (Ar ₄ ) ( Ar ₅ ). Preferably, R ₁ and R _{8 can} each independently be hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C10) -alkyl, more preferably hydrogen, deuterium, halogen, cyano or a substituted or unsubstituted (C1-C4) -alkyl , be.

Dabei gilt, dass in Formel 1-1
X für O oder S steht;
R₉ bis R₁₂ jeweils unabhängig für Wasserstoff oder Deuterium oder eine Bindungsstelle an L₂ stehen;
R₁₃ jeweils unabhängig für Wasserstoff, Deuterium, ein substituiertes oder unsubstituiertes (C6-C50)-Aryl oder ein substituiertes oder unsubstituiertes (3- bis 50-gliedriges) Heteroaryl steht;
a für eine ganze Zahl von 1 bis 4 steht und dann, wenn a eine ganze Zahl mit einem Wert von 2 oder mehr ist, jedes von R₁₃ gleich oder verschieden sein kann; und
L₁, L₂, Ar₁ und R₁ bis R₈ wie in obiger Formel 1 definiert sind.In one embodiment of the present disclosure, the compound represented by Formula 1 can be represented by the following Formula 1-1.

It applies that in formula 1-1
X represents O or S;
R ₉ to R ₁₂ each independently represent hydrogen or deuterium or a point of attachment to L ₂ ;
Each R ₁₃ independently represents hydrogen, deuterium, a substituted or unsubstituted (C6-C50) aryl, or a substituted or unsubstituted (3- to 50-membered) heteroaryl;
a is an integer from 1 to 4 and when a is an integer having a value of 2 or more, each of R _{13 may be the} same or different; and
L ₁ , L ₂ , Ar ₁ and R ₁ to R _{8 are} as defined in formula 1 above.

In one embodiment, the compound represented by Formula 1 above can be more specifically illustrated by, but not limited to, the following compounds.

In the above compounds, Dn means that n hydrogen atoms have been replaced by deuterium, where n stands for an integer with a value from 1 to 50. In one embodiment of the present disclosure, n preferably stands for an integer with a value of 8 or more and more preferably for an integer with a value of 10 or more, and even more preferably n stands for an integer with a value of 15 or more. When deuterated with a number larger than the lower limit, the bond dissociation energy increases in accordance with the deuteration, thereby increasing the stability of the connection. By using such a compound in an organic electroluminescent device, improved durability property can be obtained.

The light emitting material according to one embodiment contains at least one amine derivative represented by Formula 2 above. In one embodiment, the formula 2 above can be The compound reproduced is a fluorescent dopant, for example a fluorescent dopant for the emission of blue light.

In Formula 2 above, Ring A, Ring B and Ring C each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3- to 50-membered) heteroaryl. In one embodiment of the present disclosure, Ring A, Ring B, and Ring C each independently represent a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5- to 40-membered) heteroaryl. In another embodiment of the present disclosure, Ring A represents a substituted or unsubstituted (C6-C18) aryl and Ring B and Ring C each independently represent a substituted or unsubstituted (C6-C18) aryl or a substituted or unsubstituted (5th - up to 36-membered) heteroaryl. For example, ring A can be a substituted or unsubstituted benzene ring, an unsubstituted naphthalene ring, or an unsubstituted terphenyl ring, the substituent of the substituted benzene ring being at least one of deuterium; Methyl which is unsubstituted or substituted by at least one deuterium; tert-butyl; Diphenylamino which is unsubstituted or substituted by deuterium, methyl and / or tert-phenyl; Phenylnaphthylamino; Dinaphthylamino and a substituted or unsubstituted phenyl; Naphthyl; Biphenyl; Terphenyl; Triphenylenyl; Carbazolyl; Phenoxazinyl; Phenothiazinyl; May be dimethylacridinyl and dimethylxanthenyl and wherein the substituent of the substituted phenyl is at least one of deuterium; Methyl; carbazolyl; Dibenzofuranyl; Diphenylamino; Phenoxazinyl; Phenothiazinyl and Dimethylacridinyl can act. For example, ring B and ring C can each independently be a substituted or unsubstituted benzene ring, an unsubstituted naphthalene ring, an unsubstituted biphenyl ring, an unsubstituted dibenzothiophene ring, an unsubstituted dibenzofuran ring, a carbazole ring which is substituted by phenyl and / or diphenylamino -membered hetero ring which contains boron and nitrogen and is substituted by methyl and / or phenyl, a 25-membered hetero ring which contains boron and nitrogen and is substituted by at least one phenyl, or a 36-membered hetero ring which contains boron and nitrogen and is substituted by at least one methyl, where the substituent on the substituted benzene ring is deuterium; Methyl; tert-butyl; Phenyl; a substituted or unsubstituted diphenylamino; Phenylnaphthylamino; or phenylamino which is substituted by phenylcarbazolyl or dibenzofuranyl, and where the substituent of the substituted diphenylamino can be methyl and / or diphenylamino.

In formula 2 above, Y ₁ stands for B and X ₁ and X ₂ each independently stand for NR, where R stands for hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6 -C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy, a substituted or unsubstituted tri- (C1-C30) -alkylsilyl, a substituted or unsubstituted di- (C1-C30) -alkyl- (C6-C30) -arylsilyl, a substituted or unsubstituted (C1-C30) -alkyldi (C6-C30) -arylsilyl, a substituted or unsubstituted tri- (C6-C30) -arylsilyl or -L ₄ -N (Ar ₄ ) (Ar ₅ ) or R can be linked to at least one of ring A, ring B and ring C to form one or more rings . According to one embodiment of the present disclosure, R is in each case independently hydrogen, deuterium, a substituted or unsubstituted (C1-C20) -alkyl, a substituted or unsubstituted (C6-C25) -aryl or a substituted or unsubstituted (3- to 25-membered) ) Heteroaryl or R can be linked to at least one of ring A, ring B and ring C to form one or more rings. In another embodiment of the present disclosure, R can be hydrogen, deuterium, unsubstituted (C1-C10) -alkyl, (C6-C18) -aryl, substituted by (C1-C10) -alkyl and / or di- (C6-C18) - aryl is substituted, or (5- to 20-membered) heteroaryl which is substituted by (C6-C18) -aryl, or be linked to at least one of ring A, ring B and ring C to form one or more rings. For example, R can be hydrogen; Deuterium; Methyl; Phenyl which is unsubstituted or substituted by methyl and / or tert-butyl; Naphthyl; Biphenyl which is unsubstituted or substituted by diphenylamino; Triphenylenyl or carbazolyl which is substituted by phenyl, or be linked to at least one of ring A, ring B and ring C to form one or more rings.

According to one embodiment of the present disclosure, the compound represented by Formula 2 above can be represented by Formula 2-1 below.

It applies here that in formula 2-1
R ₂₁ to R ₃₁ each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl, a substituted or unsubstituted (3- to 30- membered) heteroaryl, a substituted or unsubstituted (C3-C30) -cycloalkyl, a substituted or unsubstituted (C1-C30) -alkoxy, a substituted or unsubstituted tri- (C1-C30) -alkylsilyl, a substituted or unsubstituted di- (C1 -C30) -alkyl- (C6-C30) -arylsilyl, a substituted or unsubstituted (C1-C30) -alkyldi (C6-C30) -arylsilyl, a substituted or unsubstituted tri- (C6-C30) -arylsilyl or -L ₄ -N (Ar ₄ ) (Ar ₅ ) or can be linked to the adjacent substituent to form one or more rings and
Y ₁ , X ₁ , X ₂ , L ₄ , Ar ₄ and Ar _{5 are} as defined in formula 2 above.

In one embodiment of the present disclosure, R ₂₁ through R _{31 can} each independently be hydrogen, deuterium, a substituted or unsubstituted (C1-C20) alkyl, a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (5- to 20-membered) heteroaryl or -L ₄ -N- (Ar ₄ ) (Ar ₅ ) or be linked to one or more rings with the adjacent substituent. In another embodiment of the present disclosure, R ₂₁ through R _{31 can} each independently be hydrogen, deuterium, unsubstituted (C1-C10) alkyl; (C6-C18) -aryl which is unsubstituted or substituted by (C1-C10) -alkyl, (13- to 18-membered) heteroaryl and / or di- (C6-C18) -arylamino; (5- to 18-membered) heteroaryl which is unsubstituted or _{substituted by (C1-C10) -alkyl or -L 4} -N- (Ar ₄ ) (Ar ₅ ), or with the adjacent substituent to form one or more rings be linked. For example, R ₂₁ to R _{31 can} each independently be hydrogen, methyl, tert-butyl, a substituted or unsubstituted phenyl, biphenyl, terphenyl, triphenylenyl, carbazolyl, phenoxazinyl, phenothiazinyl, dimethylacridinyl, dimethylxanthenyl, diphenylamino, unsubstituted or substituted by methyl and / or diphenylamino is substituted, phenylamino which is substituted by phenylnaphthylamino, dibiphenylamino, phenylcarbazolyl or dibenzofuranyl, or (17- to 21-membered) heteroaryl which is substituted by methyl and / or phenyl; or be linked to the adjacent substituent to form a benzene ring, an indole ring which is substituted by phenyl and / or diphenylamino, a benzofuran ring, a benzothiophene ring or a 19-membered hetero ring which is substituted by at least one methyl. The substituent of the substituted phenyl can be methyl, carbazolyl, dibenzofuranyl, diphenylamino, phenoxazinyl, phenothiazinyl and / or dimethylacridinyl.

In one embodiment, the compound represented by Formula 2 above can be more specifically illustrated by, but not limited to, the following compounds.

In the above compounds, D2 to D5 mean that two (2) to five (5) hydrogen atoms have each been replaced with deuterium.

The hole blocking layer and / or the electron buffer layer of the present disclosure contains at least one compound represented by Formula 11 above. That is, the compound represented by the above formula 11 may be contained in the hole blocking layer, contained in the electron buffer layer, and contained in the hole blocking layer and the electron buffer layer, respectively.

In the above formula 11, Z ₁ to Z ₃ each independently represent CR ₁₈ .

In formula 11 above, R ₁₈ each independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C50) -aryl, a substituted or unsubstituted (3- to 50-membered) heteroaryl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy, a substituted or unsubstituted tri- (C1-C30) -alkylsilyl, a substituted or unsubstituted di- (C1-C30) -alkyl- (C6-C30) -arylsilyl, a substituted or unsubstituted (C1-C30) -alkyldi (C6-C30) -arylsilyl, a substituted or unsubstituted tri- (C6-C30) -arylsilyl or -L ₄ -N (Ar ₄ ) (Ar ₅ ), with the proviso that R ₁₈ does not include 2-dimethylfluorenyl, quinolinyl and pyridyl. Preferably, R _{18 can} each independently be hydrogen, a substituted or unsubstituted (C6-C40) -aryl, a substituted or unsubstituted (5- to 45-membered) heteroaryl, more preferably hydrogen, a substituted or unsubstituted (C6-C30) -aryl or a substituted or unsubstituted (5- to 40-membered) heteroaryl, for example hydrogen, a substituted or unsubstituted phenyl, a substituted indole, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted phenylnaphthyl, a substituted biphenylnaphthyl, the is substituted by dimethyl (2-dimethylfluorenyl is excluded), fluorenyl which is substituted by diphenyl, benzofluorenyl which is substituted by dimethyl, a substituted or unsubstituted terphenyl, unsubstituted spirobifluorenyl, a substituted or unsubstituted carbazolyl, unsubstituted dibenzocarbazolyl ituted dibenzofuranyl or a substituted or unsubstituted (16- to 38-membered) heteroaryl containing at least one of N, O and S may be.

According to one embodiment of the present disclosure, the compound represented by Formula 11 can be represented by the following Formula 11-1.

It applies that in formula 11-1
A ₁ to A _{2 are} each independently defined as R ₁₈ in formula 11 above and
m is an integer from 1 to 2 and when m is 2, each of Ar _{2 may be the} same or different.
In the above formula 11-1, L ₃ can represent a single bond, a substituted or unsubstituted (C6-C50) -arylene or a substituted or unsubstituted (5- to 50-membered) heteroarylene, preferably a single bond, a substituted or unsubstituted (C6- C45) -arylene or a substituted or unsubstituted (5- to 45-membered) heteroarylene, more preferably a single bond substituted or unsubstituted (C6-C30) -arylene or a substituted or unsubstituted (5- to 30-membered) heteroarylene. For example, L ₃ can be a single bond, phenylene that is unsubstituted or substituted by pyridinyl, unsubstituted naphthylene, biphenylene that is unsubstituted or substituted by pyridinyl, unsubstituted terphenylene, unsubstituted phenylnaphthylene, unsubstituted biphenylnaphthylene, phenylnaphthylene that is substituted by phenyl, indole unsubstituted or substituted by phenyl, or unsubstituted benzocarbazolylene.

In formula 11-1 above, Ar ₃ can be a substituted or unsubstituted (C6-C50) aryl or a substituted or unsubstituted (5- to 50-membered) heteroaryl, with the proviso that 2-dimethylfluorenyl, quinolinyl and pyridyl are excluded , preferably a substituted or unsubstituted (C6-C45) -aryl or a substituted or unsubstituted (5- to 45-membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C30) -aryl or a substituted or unsubstituted (5- to 40-membered) heteroaryl. For example, Ar ₃ can be unsubstituted naphthyl, fluorenyl which is substituted by dimethyl (2-dimethylfluorenyl is excluded), fluorenyl which is substituted by diphenyl, benzofluorenyl which is substituted by dimethyl, unsubstituted phenanthrenyl, unsubstituted triphenylenyl, unsubstituted spirylobifluorenyl, unsubstituted spirobifluorenyl, is substituted by phenyl, indolyl which is substituted by phenyl, substituted or unsubstituted carbazolyl, unsubstituted dibenzothiophenyl, unsubstituted dibenzofuranyl, benzocarbazolyl which is unsubstituted or substituted by phenyl, unsubstituted or unsubstituted dibenzocarbazolyl (13-unsubstituted or unsubstituted-to-phenyl-bis-substituted-dibenzocarbazolyl or membered) heteroaryl containing at least one of N, O and S and a spiro structure. The substituent of the substituted carbazolyl can be fluorenyl which is substituted by phenyl, carbazolyl which is substituted by phenyl, methyl, phenyl, dibenzothiophenyl and / or dibenzofuranyl. The substituent of the substituted (13- to 38-membered) heteroaryl can be methyl, tert-butyl, phenyl, naphthyl and / or biphenyl.

In the above formulas 1, 2 and 11-1, L ₄ each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene.

In the above formulas 1, 2 and 11-1, Ar ₄ and Ar ₅ each independently represent hydrogen, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C2-C30) -alkenyl, a substituted or unsubstituted one fused ring consisting of an aliphatic (C3-C30) ring and an aromatic (C6-C30) ring, a substituted or unsubstituted (C6-C30) -aryl or a substituted or unsubstituted (3 to 30-membered) heteroaryl.

In one embodiment, the compound represented by Formula II above can be more specifically illustrated by, but not limited to, the following compounds.

The compound of formula 1 according to the present disclosure can be prepared by a known synthetic method. In detail, the non-deuterated compound of formula 1 can be prepared by known coupling and substitution reactions. For example, the non-deuterated compound of formula 1 can be obtained by referring to Korean Patent Laid-Open No. 2015-0010016 A (January 28, 2015) etc. The deuterated compound of Formula 1 can be prepared in a similar manner using a deuterated precursor material or, more generally, by treating a non-deuterated compound with a deuterated solvent, D6-benzene, in the presence of a Lewis acid H / D exchange catalyst such as aluminum trichloride or ethylaluminum chloride getting produced. In addition, the degree of deuteration can be controlled by varying reaction conditions such as reaction temperature. For example, the number of deuterium atoms in Formula 1 can be adjusted by controlling the reaction temperature and time, the equivalent of the acid, and so on.

The compound of formula 2 according to the present disclosure can be prepared by a known synthetic method. For example, the compound represented by Formula 2 can be used in the compounds disclosed in Korean Patent Publication No. 1876763 (July 11, 2018), Japanese Patent Publication No. 5935199 (May 20, 2016) and Korean Patent Application Laid-Open No. 2017-0130434 A (November 28, 2017) described method can be synthesized, but is not limited to it.

In addition, the compound of formula 11 or 11-1 can be obtained by referring to Korean Patent Publication No. 1741415 (May 30, 2017) and Korean Patent Disclosure No. 2015-0108332 A (September 25, 2015), 2015-0124886 A (November 6, 2015), 2015-0128590 A (November 18, 2015), 2016-0010333 A (January 17, 2016), 2016-0014556 A (February 11, 2016), 2016-0018406 A (February 17, 2016), 2016-0099471 A (August 22, 2016), 2017-0051198A (May 11, 2017) and 2017-0067643 A (June 16, 2017) etc.

The organic electroluminescent device according to an embodiment of the present disclosure includes a substrate, a first electrode formed on the substrate, an organic layer formed on the first electrode, and a second electrode facing the first electrode and formed on the organic layer.

The organic layer contains a hole injection layer, a hole transport layer formed on the hole injection layer, a light emitting layer formed on the hole transport layer, and an electron transport zone formed on the light emitting layer, and the electron transport zone includes a hole blocking layer and / or an electron buffer layer formed on the light emitting layer ( when both the hole blocking layer and the electron buffer layer are formed, the stacking order is irrelevant), an electron transport layer formed on the hole blocking layer and the electron buffer layer, respectively, and an electron injection layer formed on the electron transport layer.

The light emitting layer can be formed using a host compound and a dopant compound. The host compound and the dopant compound are as described above. When the light-emitting layer is a layer of two or more layers, each of the light-emitting layers can emit light of different colors. For example, by forming three light emitting layers each emitting blue, red, and green light, a white light emitting device can be manufactured. In addition, a yellow or orange-colored light-emitting layer can optionally also be included.

The electron transport zone refers to a zone through which electrons are moved from the second electrode to the light-emitting layer. The electron transport zone can contain an electron transporting compound, a reducing dopant, or a combination thereof. The electron-transporting compound can be at least one of the group consisting of a phenanthrene-based compound, an oxazole-based compound, an isoxazole-based compound, a triazole-based compound, an isothiazole-based compound, an oxadiazole-based compound, a thiadiazole-based compound, a perylene-based compound, an anthracene-based compound, an aluminum complex and a gallium complex. The reducing dopant can be at least one selected from the group consisting of alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, halogenated products thereof, oxides thereof, and complexes thereof. Specific examples of the reducing dopant are lithium quinolate, sodium quinolate, cesium quinolate, potassium quinolate, LiF, NaCl, CsF, Li ₂ O, BaO and BaF ₂ , but are not limited thereto.

The hole blocking layer is a layer that blocks the movement of holes injected from the anode to the cathode because the life and efficiency of the device decrease as holes pass through the light emitting layer and flow into the cathode. The thickness of the hole blocking layer can be 1 nm to 10 nm. When the thickness is 1 nm or more, the hole blocking role can in principle be satisfied, and when the thickness is less than 10 nm, there is no problem of increasing the driving voltage of the device.

The thickness of the electron buffer layer can be 1 nm or more and is not particularly limited. In detail, the thickness of the electron buffer layer can be 2 to 200 nm. The formation of the electron buffer layer on the light emitting layer can be carried out by various known methods such as a vacuum deposition method, a wet process, a laser transfer method, etc. The electron buffer layer refers to a layer that controls charge flow properties. Accordingly, the electron buffer layer can, for example, intercept electrons, block holes or reduce an energy barrier between the electron transport zone and the light-emitting layer. The electron buffer layer may be included in an organic electroluminescent device that emits all colors such as blue, red and green, and so on.

The electron transport layer and the electron injection layer can each be composed of two or more layers.

As a material for the electron injection layer, a known electron injection material can be used. Examples of these are lithium quinolate, sodium quinolate, cesium quinolate, potassium quinolate, LiF, NaCl, CsF, Li ₂ O, BaO and BaF ₂ , but are not limited thereto.

The above-described configuration of the organic electroluminescent device is only one embodiment provided, so that the content of the present disclosure can be sufficiently conveyed to those skilled in the art. The present disclosure is not limited to the corresponding embodiment and can be embodied in other embodiments.

The present disclosure may include an electron transporting compound, a reducing dopant, or a combination thereof in the electron transport zone.

In addition, the electron transport layer may further contain the above-mentioned reducing dopant. As a material for the electron injection layer, a known electron injection material can be used. Examples of these are lithium quinolate, sodium quinolate, cesium quinolate, potassium quinolate, LiF, NaCl, CsF, Li ₂ O, BaO and BaF ₂ , but are not limited thereto.

Several host materials according to the present disclosure can be used as light emitting materials for a white organic light emitting device. Various structures have been proposed for the white organic light emitting device such as a parallel arrangement method, a stacked arrangement method, or a color conversion material (CCM) method, etc., according to the arrangement of red (R), green (G) or yellowish-green (YG) or blue (B) light-emitting units. In addition, according to an embodiment, the plurality of host materials can also be applied to the organic electroluminescent device including a quantum dot (QD).

A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light emitting layer. For the hole injection layer, multiple layers can be used for the purpose of lowering a hole injection barrier (or hole injection voltage) from an anode to a hole transport layer or an electron blocking layer, and two compounds can be used for each layer at the same time. In addition, the hole injection layer can be doped with p-type dopant. The electron blocking layer is located between the hole transport layer (or hole injection layer) and the light emitting layer and blocks the overflow of electrons from the light emitting layer to restrict excitons in the light emitting layer, thereby preventing light leakage. Multiple layers can be used for the hole transport layer or the electron blocking layer, and multiple compounds can be used for each layer.

To form each layer of the organic electroluminescent device of the present disclosure, dry film formation methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc., or wet film formation methods such as ink jet printing, nozzle printing, spray coating, spin coating, dip coating, flooding, etc. can be used.

Using a wet film forming method, a thin film can be formed by dissolving or diffusing each layer forming materials in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent in which the materials constituting each layer can be dissolved or diffused and which has no problem in terms of film-formability.

The present disclosure can provide a display device using the organic electroluminescent device comprising the compound represented by Formula 1 above, the compound represented by Formula 2 above, and the compound represented by Formula 11 above. That is, it is possible to manufacture a display device or a lighting device using the organic electroluminescent device of the present disclosure. Specifically, the organic electroluminescent device of the present disclosure can be used to manufacture display devices such as white organic light emitting devices, smartphones, tablets, notebooks, PCs, televisions or display devices for cars, or lighting devices such as exterior or interior lighting.

In the following, the manufacturing method of compounds according to the present disclosure and their properties and the properties of OLED devices of the present disclosure are explained with reference to representative compounds of the present disclosure in order to understand the present disclosure in detail. However, the following examples are only used to describe the properties of the compound according to the present disclosure and the OLED device according to the present disclosure in order to understand the present invention in detail, and the present application is not limited to the following examples.

[Synthesis Example 1] Synthesis of Compound H-190

Compound H-190-1 (3.27 g, 109.8 mmol), Compound H-190-2 (22.5 g, 91.5 mmol), tetrakis (triphenylphosphine) palladium (Pd (PPh ₃ ) ₄ ) ( 5.3 g, 46 mmol), 115 ml of 2 M Na ₂ CO ₃ , 460 ml of toluene and 115 ml of ethanol (EtOH) were placed in a flask and then stirred under reflux at 140 ° C. for 2 hours. After cooling to room temperature, the organic layer was extracted with ethyl acetate, the remaining water was removed with magnesium sulfate and then dried. Next, it was separated by column chromatography, giving Compound H-190 (21.7 g, yield: 56.51%). MG Fp. H-190 420.15 247 ° C

[Synthesis Example 2] Synthesis of Compound H-206

Compound H-206-1 (10.0 g, 0.024 mol), Compound H-206-2 (7.0 g, 0.028 mol), PdCl ₂ (amphos) ₂ (0.84 g, 0.0012 mol), 50 mL of 1 M Na ₂ CO ₃ , 150 mL of toluene and Aliquat 336 (0.48 g, 0.0012 mol) were placed in a flask and then stirred at 140 ° C. for 2 hours. After the mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate and then distilled under reduced pressure. Next, it was separated by column chromatography, giving Compound H-206 (10.8 g, yield: 83.72%). MG Fp. H-206 546.6 310 ° C

[Synthesis Example 3] Synthesis of Compound B-73

Compound B-73-1 (20 g, 0.078 mol), Compound B-73-2 (43.3 g, 0.093 mol), Pd ₂ (dba) ₂ (3.6 g, 0.0039 mol), S- Phos (3.2 g, 0.0078 mol), NaOt-Bu (18.7 g, 0.194 mol) and 520 mL o-xylene were placed in a flask and then stirred under reflux at 180 ° C. for 3 hours. The mixture was cooled to room temperature and then methanol was added and the solid was filtered off under reduced pressure. The obtained solid was dissolved in chloroform and then separated by column chromatography, to give Compound B-73 (43.6 g, yield: 87.55%). MG Fp. B-73 640.7 251 ° C

[Synthesis Example 4] Synthesis of Compound B-113

1) Synthesis of Compound B-113-3

Compound B-113-1 (50.3 g, 200.34 mmol), Compound B-113-2 (50.0 g, 190.80 mmol), Pd (PPh ₃ ) ₄ (6.6 g, 5, 72 mmol), potassium carbonate (K ₂ CO ₃ ) (66.0 g, 477 mmol), 950 mL toluene, 240 mL EtOH and 240 mL distilled water (H ₂ O) were placed in a flask and then stirred under reflux for 3 hours . After the completion of the reaction, the mixture was extracted with ethyl acetate, and then separated by column chromatography, to give Compound B-113-3 (61.7 g, yield: 85%).

2) Synthesis of Compound B-113-4

Compound B-113-3 (61.7 g, 180.83 mmol) and 720 mL methanesulfonic acid (MSA) were placed in a flask and then stirred at 70 ° C. for 2 hours. After the completion of the reaction, the mixture was added _{dropwise to H 2} O and then filtered to give Compound B-113-4 (40.1 g, yield: 72%).

3) Synthesis of Compound B-113-5

Hypophosphite (H ₃ PO ₂ ) (22.0 mL, 207.53 mmol), iodine (12) (17.1 g, 67.45 mmol) and 650 mL of acetic acid (AcOH) were placed in a flask and then for 1 hour heated under reflux. Next, Compound B-113-4 (40.1 g, 129.71 mmol) was added to the mixture and then stirred under reflux for 2 hours. After the completion of the reaction, the mixture was extracted with ethyl acetate to give Compound B-113-5 (38.3 g, yield: 100%).

4) Synthesis of Compound B-113-6

Compound B-113-5 (38.3 g, 129.76 mmol), potassium iodide (Kl) (2.2 g, 12.98 mmol), potassium hydroxide (KOH) (36.4 g, 648.80 mmol), Benzyltriethylammonium chloride (TEBAC) (1.8 g, 6.49 mmol), 650 mL dimethyl sulfoxide (DMSO) and 65 mL H ₂ O were placed in a flask and then stirred at room temperature for 30 minutes. Then methyl iodide (Mel) (20.2 mL, 324.39 mmol) was added and the mixture was then stirred at room temperature for 2 hours. After the completion of the reaction, the mixture was extracted with ethyl acetate, and then separated by column chromatography, to give Compound B-113-6 (36.0 g, yield: 86%).

5) Synthesis of Compound B-113-7

Compound B-113-6 (10 g, 30.94 mmol), bis (pinacolato) diboron (11 g, 43.32 mmol), bis (triphenylphosphine) palladium (II) dichloride (PdCl ₂ (PPh ₃ ) ₂ ) (1.1 g, 1.55 mmol), potassium acetate (KOAc) (6.1 g, 61.88 mmol) and 155 mL 1,4-dioxane were placed in a flask and then stirred at 130 ° C for 6 hours. After the completion of the reaction, the mixture was cooled to room temperature and then extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and then the solvent was removed on a rotary evaporator. Next, it was separated by column chromatography, giving Compound B-113-7 (7.8 g, yield: 68%).

6) Synthesis of Compound B-113

Compound B-113-7 (3.0 g, 8.10 mmol), Compound B-113-8 (3.0 g, 7.72 mmol), Pd (PPh ₃ ) ₄ (0.3 g, 0, 23 mmol), K ₂ CO ₃ (2.0 g, 19.30 mmol), 40 mL toluene, 10 mL EtOH and 10 mL H ₂ O were placed in a flask and then stirred under reflux for 4 hours. After the completion of the reaction, the mixture was extracted with ethyl acetate, and then separated by column chromatography, to give Compound B-113 (2.8 g, yield: 67%). MG Fp. B-113 551.69 219 ° C

[Synthesis Example 5] Synthesis of Compound B-93

Compound B-93-1 (3 g, 7.1 mmol), Compound B-113-8 (3.04 g, 7.8 mmol), Pd (PPh ₃ ) ₄ (0.41 g, 0.36 mmol ), Sodium carbonate (Na ₂ CO ₃ ) (1.9 g, 17.8 mmol), 24 mL toluene, 6 mL EtOH and 6 mL H ₂ O were placed in a flask and then stirred at 120 ° C. for 4 hours. After the completion of the reaction, the mixture was added dropwise to methanol, and the obtained solid was filtered off. The obtained solid was purified by column chromatography and recrystallization to give Compound B-93 (2.3 g, yield 53.6%). MG Fp. B-93 602.70 288 ° C

[Synthesis Example 6] Synthesis of Compound B-45

Compound B-45-1 (43.8 g, 0.170 mol), Compound B-73-2 (119 g, 0.255 mol), Pd ₂ (dba) ₂ (16 g, 0.017 mol), P (t-bu) ₃ (8.5 ml, 0.034 mol), NaOt-Bu (498 g, 0.51 mol) and 900 ml of o-xylene were placed in a flask and then stirred under reflux at 180 ° C. for 2 hours.

The mixture was then cooled to room temperature and methanol was added. Next, the solid was filtered off under reduced pressure. The obtained solid was dissolved in chloroform, and then separated by column chromatography, to give Compound B-45 (38 g, yield: 35.18%). MG Fp. B-45 640.7 238 ° C

[Device Example 1-1] Manufacture of an OLED according to the present disclosure

An OLED was made in accordance with the present disclosure. First, a transparent thin electrode layer made of indium tin oxide (ITO) (10 Ω / sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was successively subjected to ultrasonic washing with acetone, ethanol and distilled water and then stored in isopropanol and then used. After evacuation until a vacuum of 10 ^-6 Torr was reached in the chamber, the ITO substrate was attached to a substrate holder of a vacuum vapor deposition apparatus. Then, the compound HT-1 described in the following Table 1 was charged as the first hole injection compound in a cell of the vacuum vapor deposition apparatus, and the compound HI-1 described in the following Table 1 was charged in another cell of the vacuum vapor deposition apparatus. The two materials were evaporated at different rates, and Compound HI-1 was deposited in a doping amount of 3% by weight based on the total amount of Compound HT-1 and Compound HI-1 to form a hole injection layer having a thickness of 10 to form nm. Next, Compound HT-1 was deposited as a first hole transport layer to a thickness of 75 nm on the hole injection layer. Next, Compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus and evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 5 nm on the first hole transport layer. After the formation of the hole injection layer and the hole transport layers, a light emitting layer was formed thereon as follows: Compound H-190 was introduced into one cell of the vacuum vapor deposition apparatus as a host, and Compound BD was introduced into another cell as a dopant. The two materials were evaporated at different rates, and the dopant was deposited in a doping amount of 2 wt% based on the total amount of the host and the dopant to form a light emitting layer with a thickness of 20 nm on the second hole transport layer form. Next, Compound B-73 was deposited as a hole blocking layer to a thickness of 5 nm on the light emitting layer. Next, Compound ET-1 and Compound EI-1 were evaporated in two other cells at a rate of 1: 1 to form an electron transport layer with a thickness of 30 nm on the hole blocking layer. Next, after the compound EI-1 was deposited as an electron injection layer with a thickness of 2 nm using another vacuum vapor deposition apparatus, an Al cathode was deposited with a thickness of 80 nm. This is how an OLED was made.

The time for the luminance to decrease from 100% to 95% at a luminance of 1400 Nit (service life; T95) for the organic electroluminescent device produced as described above according to device example 1-1 was 56 hours.

[Device Example 1-2] Manufacture of an OLED according to the present disclosure

An OLED was manufactured in the same manner as in Device Example 1-1 except that Compound B-113 was used as the material of the hole blocking layer.

The time until the luminance decreases from 100% to 95% at a luminance of 1400 Nit (service life; T95) for the organic electroluminescent device produced as described above according to device example 1-2 was 59 hours.

[Device Example 1-3] Manufacture of an OLED according to the present disclosure

An OLED was manufactured in the same manner as Device Example 1-1 except that Compound B-93 was used as the material of the hole blocking layer.

The time until the luminance decreases from 100% to 95% at a luminance of 1400 Nit (service life; T95) for the organic electroluminescent device produced as described above according to device example 1-3 was 60 hours.

[Device Example 1-4] Manufacture of an OLED according to the present disclosure

An OLED was manufactured in the same manner as in Device Example 1-1 except that Compound B-45 was used as the material of the hole blocking layer.

The time until the luminance decreases from 100% to 95% at a luminance of 1400 Nit (service life; T95) for the organic electroluminescent device produced as described above according to device example 1-4 was 52 hours.

[Device Example 1-5] Manufacture of an OLED according to the present disclosure

An OLED was manufactured in the same manner as in Device Example 1-1 except that Compound H-206 was used as the host material of the light-emitting layer and Compound B-73 was used as the material of the hole blocking layer.

The driving voltage and the current efficiency (cd / A) at a luminance of 1000 nits for the above-manufactured organic electroluminescent device according to Device Example 1-5 were 4.0 V and 5.7 cd / A, respectively.

[Device Example 1-6] Manufacture of an OLED according to the present disclosure

An OLED was manufactured in the same manner as in Device Example 1-1 except that Compound H-206 was used as the host material of the light-emitting layer and Compound B-113 was used as the material of the hole blocking layer.

The driving voltage and the current efficiency (cd / A) at a luminance of 1000 nits for the organic electroluminescent device according to Device Example 1-6 manufactured as described above were 3.9 V and 5.7 cd / A, respectively.

[Device Example 1-7] Manufacture of an OLED according to the present disclosure

An OLED was manufactured in the same manner as in Device Example 1-1 except that Compound H-206 was used as the host material of the light-emitting layer and Compound B-93 was used as the material of the hole blocking layer.

The driving voltage and the current efficiency (cd / A) at a luminance of 1000 nits for the above-manufactured organic electroluminescent device according to Device Example 1-8 were 4.0 V and 5.5 cd / A, respectively.

[Device Example 1-8] Manufacture of an OLED according to the present disclosure

An OLED was manufactured in the same manner as in Device Example 1-1 except that Compound H-206 was used as the host material of the light-emitting layer and Compound B-45 was used as the material of the hole blocking layer.

The driving voltage and the current efficiency (cd / A) at a luminance of 1000 nits for the above-manufactured organic electroluminescent device according to Device Example 1-7 were 4.0 V and 5.7 cd / A, respectively.

[Comparative Example 1-1] Manufacture of an OLED using the conventional compound

An OLED was manufactured in the same manner as in Device Example 1-1 except that Compound Balq was used as the material of the hole blocking layer.

The time until the luminance decreases from 100% to 95% at a luminance of 1400 Nit (lifetime; T95) for the organic electroluminescent device produced as described above according to Comparative Example 1-1 was 29 hours.

[Comparative Example 1-2] Manufacture of an OLED using the conventional compound

An OLED was fabricated in the same manner as in Device Example 1-1 except that Compound H-206 was used as the host material of the light emitting layer and Compound Balq was used as the material of the hole blocking layer.

The driving voltage and the current efficiency (cd / A) at a luminance of 1000 nits for the above-manufactured organic electroluminescent device according to Comparative Example 1-2 were 4.3 V and 5.5 cd / A, respectively.

It has been confirmed that the organic electroluminescent device produced by using a combination of host and dopant in a light emitting layer and a hole blocking material as specified in the present disclosure has properties such as long life, low drive voltage and / or high current efficiency compared to the conventional organic shows electroluminescent device. In addition, due to the combination of the present disclosure, the hole blocking layer can provide a blue light emitting organic electroluminescent device with a long life by blocking the holes and controlling the property of the injected electrons, thereby maintaining the life balance with the red and green light emitting organic electroluminescent devices will. Without wishing to be bound by any theory, in general, in realizing a display, a high driving voltage in a blue light emitting device among red light, green light, and blue light emitting devices is an obstacle to white light realization and power consumption saving relative to the red light and green light devices. Therefore, it can be a very important point to lower the drive voltage of the blue device even slightly. By manufacturing a device to which a combination of compounds of the present disclosure is applied, a device with a low driving voltage can be realized.

Lichtemittierende Schicht

Lochblockierschicht

Elektronentransport/schicht Elektroneninjektions -/schicht

The compounds used in the above Device Examples and Comparative Examples are shown in Table 1 below. [Table 1] Hole injection layer / hole transport layer

Light emitting layer

Hole blocking layer

Electron transport / layer electron injection / layer

QUOTES INCLUDED IN THE DESCRIPTION

This list of the documents listed by the applicant was generated automatically and is included solely for the better information of the reader. The list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions.

Patent literature cited

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Non-patent literature cited

• App. Phys. Lett. 51, 913, 1987 [0002]

Claims (10)

An organic electroluminescent device comprising a first electrode; a second electrode facing the first electrode; a light-emitting layer between the first electrode and the second electrode and an electron transport zone between the light-emitting layer and the second electrode, wherein the electron transport zone contains a hole blocking layer and / or an electron buffer layer and an electron transport layer and an electron injection layer, the electron transport layer between the hole blocking layer or the Electron buffer layer and the second electrode is formed, wherein the electron injection layer is formed between the electron transport layer and the second electrode, wherein the light-emitting layer comprises a compound represented by the following formula 1 and a compound represented by the following formula 2, and wherein the hole blocking layer and / or the electron buffer layer comprise a compound represented by the following formula 11;

wherein L ₁ and L ₂ each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5- to 30-membered) heteroarylene; Ar ₁ and Ar ₂ each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5- to 30-membered) heteroaryl; and R ₁ to R ₈ each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl, a substituted or unsubstituted (3-30 -linked) Heteroaryl, a substituted or unsubstituted (C3-C30) -cycloalkyl, a substituted or unsubstituted (C1-C30) -alkoxy, a substituted or unsubstituted tri- (C1-C30) -alkylsilyl, a substituted or unsubstituted di- (C1-C30) ) -alkyl- (C6-C30) -arylsilyl, a substituted or unsubstituted (C1-C30) -alkyldi (C6-C30) -arylsilyl, a substituted or unsubstituted tri- (C6-C30) -arylsilyl or -L ₄ - N (Ar ₄ ) (Ar ₅ );

wherein ring A, ring B and ring C each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3- to 50-membered) heteroaryl; Y _{1 represents} B; X ₁ and X ₂ each independently represent NR; and R represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl substituted or unsubstituted (C3-C30) -cycloalkyl, a substituted or unsubstituted (C1-C30) -alkoxy, a substituted or unsubstituted tri- (C1-C30) -alkylsilyl, a substituted or unsubstituted di- (C1-C30) -alkyl - (C6-C30) -arylsilyl, a substituted or unsubstituted (C1-C30) -alkyldi (C6-C30) -arylsilyl, a substituted or unsubstituted tri- (C6-C30) -arylsilyl or -L ₄ -N (Ar ₄ ) (Ar ₅ ) or can be linked to at least one of Ring A, Ring B and Ring C to form one or more rings;

where Z ₁ to Z ₃ each independently represent CR ₁₈ ; R ₁₈ each independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C50) -aryl, a substituted or unsubstituted (3 to 50-membered) heteroaryl , a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, a substituted or unsubstituted (C1-C30) -alkoxy, a substituted or unsubstituted tri- (C1-C30) -alkylsilyl, a substituted or unsubstituted di- (C1-C30) -alkyl- (C6-C30) -arylsilyl, a substituted or unsubstituted (C1-C30) -alkyldi- (C6-C30) -arylsilyl, a substituted or unsubstituted tri - (C6-C30) -arylsilyl or -L ₄ -N (Ar ₄ ) (Ar ₅ ) with the proviso that R ₁₈ does not include 2-dimethylfluorenyl, quinolinyl and pyridyl; L ₄ each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar ₄ and Ar ₅ each independently represent hydrogen, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C2-C30) -alkenyl, a substituted or unsubstituted fused ring from an aliphatic (C3-C30) ring and an aromatic (C6-C30) ring, a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3 to 30-membered) heteroaryl; and when there are plural substituents represented by the same symbol, each of the substituent represented by the same symbol may be the same or different. Organic electroluminescent device according to Claim 1 , wherein the substituent of the substituted alkyl, the substituted alkenyl, the substituted aryl, the substituted aryl, the substituted heteroaryl, the substituted heteroarylene, the substituted cycloalkyl, the substituted alkoxy, the substituted heterocycloalkyl, the substituted trialkylsilyl, the substituted trialkylsilyl, the substituted trialkylsilyl , the substituted alkyldiarylsilyl, the substituted triarylsilyl, and the substituted fused ring of an aliphatic ring and an aromatic ring each independently around at least one selected from the group consisting of deuterium; Halogen; Cyano; Carboxyl; Nitro; Hydroxy; (C1-C30) alkyl; Halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3- to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (5- to 50-membered) heteroaryl which is unsubstituted or substituted by (C1-C30) -alkyl, (C6-C30) -aryl and / or di- (C6-C30) -arylamino; (C6-C30) -aryl which is unsubstituted or substituted by (C1-C30) -alkyl, (3- to 50-membered) heteroaryl and / or mono- or di- (C6-C30) -arylamino; Tri- (C1-C30) alkylsilyl; Tri- (C6-C30) arylsilyl; Di- (C1-C30) -alkyl- (C6-C30) -arylsilyl; (C1-C30) -alkyldi (C6-C30) -arylsilyl; Amino; Mono- or di- (C1-C30) -alkylamino; Mono- or di- (C2-C30) -alkenylamino; Mono- or di- (C6-C30) -arylamino which is unsubstituted or substituted by (C1-C30) -alkyl, (5- to 30-membered) heteroaryl and / or di- (C6-C30) -arylamino; Mono- or di- (3- to 30-membered) heteroarylamino; (C1-C30) -alkyl- (C2-C30) -alkenylamino; (C1-C30) -alkyl- (C6-C30) -arylamino; (C1-C30) -alkyl- (3- to 30-membered) heteroarylamino; (C2-C30) -alkenyl- (C6-C30) -arylamino; (C2-C30) -alkenyl- (3- to 30-membered) heteroarylamino; (C6-C30) aryl (3 to 30 membered) heteroarylamino; (C1-C30) -alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; Di (C6-C30) arylboronyl; Di (C1-C30) alkylboronyl; (C1-C30) -alkyl- (C6-C30) -arylboronyl; (C6-C30) -Ar- (C1-C30) -alkyl and (C1-C30) -alkyl- (C6-C30) -aryl. Organic electroluminescent device according to Claim 1 , where L ₁ and L ₂ in formula 1 each independently represent a single bond or are selected from one of the substituents listed in the following group 1:

where Z is O, S, NR ₁₀₁ , CR ₁₀₂ R ₁₀₃ or SiR ₁₀₄ R ₁₀₅ ; R ₁₀₁ to R ₁₀₅ each independently represent a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl or with the adjacent one Substituents can be linked to form one or more rings; and each of the two * in each group 1 radical stands for a binding site to the anthracene skeleton and a binding site to Ar ₁ and Ar ₂ , respectively. Organic electroluminescent device according to Claim 1 , where Ar ₁ and Ar ₂ in formula 1 are each independently selected from one of the substituents listed in group 2 below:

where A, G, E and M each independently represent O, S, NR ₁₀₆ , CR ₁₀₇ R _108, or SiR ₁₀₉ R ₁₁₀ ; R ₁₀₆ to R ₁₁₀ each independently represent a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl or a substituted or unsubstituted (3- to 30-membered) heteroaryl or with the neighboring one Substituents can be linked to form one or more rings; and * stands for a binding site to the anthracene skeleton, L ₁ or L ₂ . Organic electroluminescent device according to Claim 1 , wherein the compound represented by Formula 1 is represented by the following Formula 1-1:

where X is O or S; R ₉ to R ₁₂ each independently represent hydrogen or deuterium or a point of attachment to L ₂ ; Each R ₁₃ independently represents hydrogen, deuterium, a substituted or unsubstituted (C6-C50) aryl, or a substituted or unsubstituted (3- to 50-membered) heteroaryl; a is an integer from 1 to 4 and when a is an integer having a value of 2 or more, each of R _{13 may be the} same or different; and L ₁ , L ₂ , Ar ₁ and R ₁ to R ₈ as in Claim 1 are defined. Organic electroluminescent device according to Claim 1 , wherein the compound represented by Formula 2 is represented by the following Formula 2-1:

where R ₂₁ to R ₃₁ each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C6-C30) -aryl, a substituted or unsubstituted (3- to 30th) -membered) heteroaryl, a substituted or unsubstituted (C3-C30) -cycloalkyl, a substituted or unsubstituted (C1-C30) -alkoxy, a substituted or unsubstituted tri- (C1-C30) -alkylsilyl, a substituted or unsubstituted di- ( C1-C30) -alkyl- (C6-C30) -arylsilyl, a substituted or unsubstituted (C1-C30) -alkyldi (C6-C30) -arylsilyl, a substituted or unsubstituted tri- (C6-C30) -arylsilyl or - L ₄ -N (Ar ₄ ) (Ar ₅ ) or can be linked to the adjacent substituent to form one or more rings; and Y ₁ , X ₁ , X ₂ , L ₄ , Ar ₄ and Ar ₅ as in Claim 1 are defined. Organic electroluminescent device according to Claim 1 , wherein the compound represented by Formula 11 is represented by the following Formula 11-1:

where A ₁ to A _{2 are} each independently defined as R ₁₈ in formula 11; L _{3 represents} a single bond, a substituted or unsubstituted (C6-C50) -arylene or a substituted or unsubstituted (5- to 50-membered) heteroarylene; Ar _{3 is} a substituted or unsubstituted (C6-C50) aryl or a substituted or unsubstituted (5- to 50-membered) heteroaryl, with the proviso that Ar _{3 is} not 2-dimethylfluorenyl, quinolinyl and pyridyl; and m is an integer from 1 to 2 and when m is 2, each of Ar _{3 may be the} same or different. Organic electroluminescent device according to Claim 1 , wherein the compound represented by Formula 1 is selected from the following compounds:

where Dn means that n hydrogen atoms have been replaced by deuterium, where n is an integer with a value from 1 to 50. Organic electroluminescent device according to Claim 1 wherein the compound represented by Formula 2 is selected from the following compounds:

where D2 to D5 represent that two to five hydrogen atoms have each been replaced by deuterium. Organic electroluminescent device according to Claim 1 wherein the compound represented by Formula 11 is selected from the following compounds: