DE112019006287T5 - ORGANIC ELECTROLUMINESCENT JOINT AND THIS COMPREHENSIVE ORGANIC ELECTROLUMINESCENT DEVICE - Google Patents

Abstract

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By incorporating the organic electroluminescent compound according to the present disclosure, an organic electroluminescent device with improved luminous efficiency can be provided.

Description

Technical area

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.

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. The first organic EL device was developed by Eastman Kodak in 1987 by using small aromatic diamine molecules and aluminum complexes as materials to form a light emitting layer [ Appl. Phys. Lett. 51,913,1987 ].

An organic EL device (OLED) converts electrical energy into light by injecting a charge into an organic light emitting material and commonly includes an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer of the organic EL device may be composed of a hole injection layer, a hole transport layer, a hole auxiliary layer, an auxiliary light emitting 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 . exist. The materials used in the organic layer can be classified into 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, an electron buffering material, a hole blocking material, an electron transporting material, an electron injection material, etc. depending on the function. In the organic EL device, by applying voltage, holes from an anode and electrons from a cathode are injected into a light-emitting layer, and a high-energy exciton is generated by recombining the holes and electrons. As a result of the energy, the organic light-emitting compound changes into an excited state and emits light from energy when the organic light-emitting compound returns from the excited state to the ground state.

The important factor that determines the light output in an organic EL device is light emitting materials. The light-emitting materials are required to have a high quantum efficiency, a high degree of movement of an electron and a hole, and uniformity and stability of the formed light-emitting material layer. Such light emitting materials are classified into blue, green and red light emitting materials according to the light emission color, and further include yellow or orange light emitting materials. In addition, the light-emitting materials are divided into a host material and a dopant material in a functional aspect. Recently, there is an urgent task to develop an organic EL device 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 materials is urgently required. For this purpose, the desirable properties of the host material, which functions as a solvent and the only energy transporter in the solid, should be highly pure and have a suitable molecular weight to enable vacuum deposition. Furthermore, a host material must have a high glass transition temperature and pyrolysis temperature in order to achieve thermal stability, have high electrochemical stability in order to achieve long life, be easily formable into an amorphous thin film, have good adhesion to adjacent layers, and no movement between layers demonstrate.

In addition, materials are required to be developed which have good thermal stability in a hole transport layer, a buffer layer, an electron transport layer, etc. and can improve the performance of an organic electroluminescent device such as driving voltage, luminous efficiency and life.

the JP 5,609,256 B2 discloses a 2-aminocarbazole compound suitable for a hole transport material of the organic EL device; however, it does not disclose a compound substituted in the 1-position of carbazole by an amino compound.

Disclosure of the invention

Technical task

The object of the present disclosure is to provide an organic electroluminescent compound capable of firstly producing an organic electroluminescent device with improved luminous efficiency and secondly to provide the organic electroluminescent device comprising the organic electroluminescent compound.

Solution of the task

In the course of the present invention, it has been found that an organic electroluminescent device has an improved luminous efficiency by including the specific compound containing a structure in which an amino compound is bound in the A1 position of carbazole in a hole transport layer and / or a light emitting layer can show that the present invention has been completed. Specifically, the above object can be achieved by an organic electroluminescent compound represented by the following formula 1, so that the present invention has been completed.

It applies that in Formula 1
Ar ₁ to Ar ₃ each independently represent hydrogen, deuterium, 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 mono- or di- (C1-C30) -alkylamino, a substituted or unsubstituted mono- or di- (C6-C30) -arylamino or a substituted or unsubstituted (C1-C30) -alkyl- (C6-C30 ) -arylamino;
L ₁ and L ₂ each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene;
R ₁ and R ₂ 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, a substituted one or unsubstituted mono- or di- (C1-C30) -alkylamino, a substituted or unsubstituted mono- or di- (C6-C30) -arylamino or a substituted or unsubstituted (C1-C30) -alkyl- (C6-C30) - arylamino stand;
A stands for an integer with a value from 1 to 4, b stands for an integer with a value from 1 to 3, c stands for an integer with a value of 1 or 2, with the proviso that if L _{2 represents} a single bond, c is 1; and
then when a, b and c are 2 or more, each of R ₁ , each of R _2, and each of -NAr ₂ Ar _{3 may be the} same or different.

Advantageous Effects of the Invention

The organic electroluminescent device with improved luminous efficiency can be manufactured by incorporating an organic electroluminescent compound according to the present disclosure.

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.

The present disclosure relates to an organic electroluminescent compound represented by Formula 1. In particular, the present disclosure relates to an organic electroluminescent material comprising the organic electroluminescent compound and an organic electroluminescent device comprising the organic electroluminescent compound.

The term “organic electroluminescent compound” in the present disclosure means a compound that can be used in an organic electroluminescent device and, as required, can be contained in any material layer from which an organic electroluminescent device is constructed.

The term “organic electroluminescent material” in the present disclosure means a material which can be used in an organic electroluminescent device and which 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 or an electron injection material, and so on . Act.

“(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, tert-butyl, and so on. “(C3-C30) -cycloalkyl” is 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. “(C6-C30) -aryl (en)” is a monocyclic or fused ring radical which is derived from an aromatic hydrocarbon with 6 to 30 ring skeleton carbon atoms, the number of ring skeleton carbon atoms preferably 6 to 20 and more preferably 6 to 15, can be partially saturated and can comprise a spiro structure. Examples of the aryl are specifically phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, benzofluorenyl, benzohenylbenzofluorenyl, phenylbenzofluorenyl, phenylbenzofluorenyl, phenylbenzofluorenyl, phenylbenzofluorenyl, phenylbenzofluorenyl, phenylbenzofluorenyl, phenylbenzofluorenyl, phenyl-benzofluorenyl, phenylnaphthyl, binaphthyl, phenylnaphthyl, binaphthyl, phenyl-benzofluorenyl, phenyl-benzofluorenyl, , Pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro [fluoren-fluorene] yl, spiro [fluorenbenzofluoren] yl, azulenyl, etc. More specifically, it can be around o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, pt-butylphenyl, p - (2-Phenylpropyl) phenyl, 4'-methylbiphenyl, 4 "-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, 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, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 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, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 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, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, etc. act.

“(3- to 30-membered) heteroaryl (en)” is an aryl with 3 to 30 ring skeleton atoms, the number of ring skeleton atoms preferably being 5 to 25, and at least one, preferably 1 to 4, heteroatoms from the group consisting of B, N, O, S, Si, P and Ge.

The above heteroaryl may be a monocyclic ring or a fused ring condensed with at least one benzene ring and may be partially saturated. In addition, the above heteroaryl can be a heteroaryl formed by linking at least one heteroaryl or aryl group to a heteroaryl group through one or more single bonds, and it can comprise a spiro structure. Specifically, examples of the heteroaryl may be monocyclic ring type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyridaryl, pyridaryl, ring-type, and pyridaryl-type, etc. including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, Benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, Azacarbazolyl, Benzocarbazolyl, Dibenzocarbazolyl , Phenoxazinyl, phenanthridinyl, benzodioxolyl, indolizidinyl, acrylidinyl, silafluorenyl, germafluorenyl, etc. include. More specifically, the heteroaryl can be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-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-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-indolizidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 7-imidazopyridinyl 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-Ch inolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-Ccarbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazol-1-yl, azacarbazol-2-yl, azacarbazol-3-yl, azacarbazol-4-yl, azacarbazol-5-yl, azacarbazol-6-yl, azacarbazol- 7-yl, azacarbazol-8-yl, azacarbazol-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10- Phenanthridinyl, 1-acrylidinyl, 2-acrylidinyl, 3-acrylidinyl, 4-acrylidinyl, 9-acrylidinyl, 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-t-butylpyrrol-4-yl, 3- (2-phenylpropyl) pyrrol-1-yl, 2-methyl-1-indolyl, 4 -Methyl-1-indoly 1,2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4- t-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-2-silafluorenyl, 1-2-silafluorenyl, Silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, etc.

"Halogen" here 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.

“A ring formed when linked to an adjacent substituent” means here a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic, aromatic ring or a combination thereof and formed by linking or fusing two or more adjacent substituents can preferably be a substituted or unsubstituted (3 to 26-membered) mono- or polycyclic, alicyclic, aromatic ring or a combination thereof. In addition, at least one of the carbon atoms in the ring formed can be replaced by at least one heteroatom from the group consisting of B, N, O, S, Si and P, preferably 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 to 15. In one embodiment, the fused ring can be e.g. B. a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzothiophene ring , a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted carbazole ring, and so on.

In addition, “substituted” in the expression “substituted or unsubstituted” means that a hydrogen atom in a specific functional group has been replaced by another atom or a functional group, ie a substituent. In the case of the substituents of the substituted (C1-C30) -alkyl, des substituted (C6-C30) -aryl (en) s, substituted (3- to 30-membered) heteroaryl (en) s, substituted (C3-C30) -cycloalkyl, substituted (C1-C30) -alkoxy, des substituted tri- (C1-C30) -alkylsilyl, the substituted di- (C1-C30) -alkyl- (C6-C30) -arylsilyl, the substituted (C1-C30) -alkyldi (C6-C30) -arylsilyl, des substituted tri- (C6-C30) -arylsilyl, the substituted mono- or di- (C1-C30) -alkylamino, the substituted mono- or di- (C6-C30) -arylamino and the substituted (C1-C30) -alkyl - (C6-C30) -arylaminos in Ar ₁ to Ar ₃ , L _i to L ₃ , R ₁ and R ₂ are each independently at least one from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxyl , (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, through (C6-C30) - Aryl substituted or un substituted (5- to 30-membered) heteroaryl, (5- to 30-membered) heteroaryl-substituted or unsubstituted (C6-C30) -aryl, 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 , (C1-C30) -alkyl-substituted or unsubstituted mono- or di- (C6-C30) -arylamino, (C1-C30) -alkyl- (C6-C30) -arylamino, (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. For example, the substituents can be an unsubstituted methyl, an unsubstituted phenyl, an unsubstituted biphenyl or an unsubstituted naphthyl, etc.

The following describes the organic electroluminescent compound according to an embodiment.

The organic electroluminescent compound according to one embodiment is represented by Formula 1 below.

In den Formeln 2 und 3 gilt, dass
Ar₁ bis Ar₃, L₁, L₂, R₁ und R₂, a und b wie in Formel 1 definiert sind und
L₃ für ein substituiertes oder unsubstituiertes (C6-C30)-Arylen oder ein substituiertes oder unsubstituiertes (3- bis 30-gliedriges) Heteroarylen steht.
In einer Ausführungsform steht L₁ für eine Einfachbindung, ein substituiertes oder unsubstituiertes (C6-C30)-Arylen oder ein substituiertes oder unsubstituiertes (3- bis 30-gliedriges) Heteroarylenund kann vorzugsweise eine Einfachbindung oder ein substituiertes oder unsubstituiertes (C6-C25)-Arylen und weiter bevorzugt eine Einfachbindung oder ein substituiertes oder unsubstituiertes (C6-C18)-Arylen sein. Beispielsweise kann es sich bei L₁ um eine Einfachbindung, ein substituiertes oder unsubstituiertes Phenylen, ein substituiertes oder unsubstituiertes Biphenylen oder ein substituiertes oder unsubstituiertes Naphthylen handeln.It applies that in Formula 1
Ar ₁ to Ar ₃ each independently represent hydrogen, deuterium, 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 mono- or di- (C1-C30) -alkylamino, a substituted or unsubstituted mono- or di- (C6-C30) -arylamino or a substituted or unsubstituted (C1-C30) -alkyl- (C6-C30 ) -arylamino;
L ₁ and L ₂ each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene;
R ₁ and R ₂ 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, a substituted one or unsubstituted mono- or di- (C1-C30) -alkylamino, a substituted or unsubstituted mono- or di- (C6-C30) -arylamino or a substituted or unsubstituted (C1-C30) -alkyl- (C6-C30) - arylamino stand;
A stands for an integer with a value from 1 to 4, b stands for an integer with a value from 1 to 3, c stands for an integer with a value of 1 or 2, with the proviso that if L _{2 represents} a single bond, c is 1; and
then when a, b and c are 2 or more, each of R ₁ , each of R _2, and each of -NAr ₂ Ar _{3 may be the} same or different.
The organic electroluminescent compound of Formula 1 in one embodiment can be represented by the following Formula 2 or 3:

In formulas 2 and 3 it applies that
Ar ₁ to Ar ₃ , L ₁ , L ₂ , R ₁ and R ₂ , a and b are as defined in formula 1 and
L _{3 represents} a substituted or unsubstituted (C6-C30) -arylene or a substituted or unsubstituted (3 to 30-membered) heteroarylene.
In one embodiment, L ₁ stands for a single bond, a substituted or unsubstituted (C6-C30) -arylene or a substituted or unsubstituted (3 to 30-membered) heteroarylene and can preferably be a single bond or a substituted or unsubstituted (C6-C25) - Arylene and more preferably a single bond or a substituted or unsubstituted (C6-C18) -arylene. For example, L _{1 can} be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene or a substituted or unsubstituted naphthylene.

In one embodiment, Ar _{1 represents} hydrogen, deuterium, 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 mono- or di- (C1-C30) -alkylamino, a substituted or unsubstituted mono- or di- (C6-C30) -arylamino or a substituted or unsubstituted (C1-C30) -alkyl- (C6-C30) -arylamino and can preferably be hydrogen, deuterium or a substituted or unsubstituted (C6-C25) -aryl and more preferably a substituted or unsubstituted (C6-C18) -aryl. For example, Ar _{1 can} be a substituted or unsubstituted phenyl, a substituted or unsubstituted o-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted p- Act terphenyl or a substituted or unsubstituted m-terphenyl.

In one embodiment, L ₂ stands for a single bond, a substituted or unsubstituted (C6-C30) -arylene or a substituted or unsubstituted (3 to 30-membered) heteroarylene and can preferably be a single bond or a substituted or unsubstituted (C6-C25) -Arylene and more preferably a single bond or a substituted or unsubstituted (C6-C18) -arylene. For example, L _{2 can} be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted p-biphenylene, a substituted or unsubstituted m-biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted phenylnaphthylene or a substituted or unsubstituted naphthylphenylene Act.

In one embodiment, L _{3 can} be a substituted or unsubstituted (C6-C30) -arylene or a substituted or unsubstituted (3 to 30-membered) heteroarylene, preferably a substituted or unsubstituted (C6-C25) -arylene preferably a substituted or unsubstituted (C6-C18) arylene act. For example, L ₃ can be substituted or unsubstituted phenylene.

In one embodiment, Ar ₂ and Ar _{3 represent} hydrogen, deuterium, 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 mono- or di- (C1-C30) -alkylamino, a substituted or unsubstituted mono- or di- (C6-C30) -arylamino or a substituted or unsubstituted (C1-C30) -alkyl- (C6 -C30) -arylamino and can preferably be hydrogen, deuterium, a substituted or unsubstituted (C6-C30) -aryl or a substituted or unsubstituted (3 to 25-membered) heteroaryl and more preferably a substituted or unsubstituted (C6-C25) - Aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl.

In one embodiment, Ar ₂ and Ar _{3 can} each be independently selected from one of the substituents listed in Group 1 below.

It applies that in group 1
A1 to A3 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; and
L stands for a substituted or unsubstituted (C6-C30) -arylene or a substituted or unsubstituted (3 to 30-membered) heteroarylene.

In group 1, A1 and A2 can preferably each independently be a substituted or unsubstituted (C1-C10) -alkyl or a substituted or unsubstituted (C6-C18) -aryl, more preferably a substituted or unsubstituted (C1-C6) - Alkyl or a substituted or unsubstituted (C6-C12) aryl.

In group 1, A3 can preferably be a substituted or unsubstituted (C6-C25) -aryl, more preferably a substituted or unsubstituted (C6-C18) -aryl.

For example, Ar ₂ and Ar _{3 can} each independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted o-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted fluorenyl substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenyl act.

In one embodiment, R ₁ and R ₂ 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, a substituted or unsubstituted mono- or di- (C1-C30) -alkylamino, a substituted or unsubstituted mono- or di- (C6-C30) -arylamino or a substituted or unsubstituted (C1-C30) -alkyl- (C6-C30) -arylamino and can preferably be hydrogen, deuterium , Halogen, cyano or a substituted or unsubstituted (C6-C25) -aryl and more preferably hydrogen, deuterium or a substituted or unsubstituted (C6-C18) -aryl. For example, R ₁ and R _{2 can} each independently be hydrogen or a substituted or unsubstituted phenyl.

_{According to one embodiment, Ar 1} to Ar ₃ in the organic electroluminescent compound of the formula 1 can each independently represent a substituted or unsubstituted (C6-C30) -aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl; L ₁ and L ₂ each independently represent a single bond, a substituted or unsubstituted (C6-C25) arylene or a substituted or unsubstituted (5- to 15-membered) heteroarylene, and R ₁ and R ₂ each independently represent hydrogen, a substituted one or unsubstituted (C1-C6) -alkyl or a substituted or unsubstituted (C6-C12) -aryl.

According to one embodiment, in the organic electroluminescent compound of the formula 1, Ar ₁ to Ar _{3 can} each independently represent a (C6-C30) -aryl which is unsubstituted or substituted by at least one of (C1-C6) -alkyl and (C6-C12) - Aryl is substituted, or a (C6-C12) -aryl substituted or unsubstituted (5- to 20-membered) heteroaryl; L ₁ and L ₂ each independently represent a single bond or an unsubstituted (C6-C18) -alkylene and R ₁ and R ₂ each independently represent hydrogen or an unsubstituted (C6-C12) -aryl.

In one embodiment, the compound represented by Formula 1 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 synthesized according to, but not limited to, the following Reaction Scheme 1 or 2, and can be prepared by a synthetic method known to those skilled in the art.

In Reaction Schemes 1 and 2, the definitions of the substituents are as defined in Formula 1.

As described above, exemplary synthesis examples of the compounds represented by Formula 1 are described according to an embodiment, but they are based on Buchwald-Hartwig cross-coupling reaction, N-arylation reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, Grignard reaction, Heck reaction, SN ₁ substitution reaction, SN ₂ substitution reaction and phosphine-mediated reductive cyclization reaction, etc. It will be apparent to those skilled in the art that the above reaction proceeds even if other substituents defined in Formula 1, which are different from those described in the specific synthesis examples, are bound.

The present disclosure can provide an organic electroluminescent material comprising the organic electroluminescent compound of Formula 1 and an organic electroluminescent device comprising the organic electroluminescent material.

The organic electroluminescent material can consist solely of the organic electroluminescent compound of the present disclosure or further comprise conventional materials incorporated into the organic electroluminescent material. When two or more species of materials are contained in a layer, the at least two compounds can be a mixture evaporation or a co-evaporation to form a layer. The organic electroluminescent material according to one embodiment can comprise at least one compound represented by the formula 1. For example, the compound of the formula 1 can be contained in a hole transport layer and / or a light-emitting layer; preferably, the organic electroluminescent compound of the formula 1 of the present disclosure can be contained as the hole transport material of the organic electroluminescent device.

An organic electroluminescent material of the present disclosure may contain a host compound other than the organic electroluminescent compound of Formula 1; The organic light-emitting material can preferably also contain at least one dopant.

The dopant contained in the organic electroluminescent material of the present disclosure can be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but it may preferably be one or more metalated complex compounds of one or more metal atoms composed of iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) are selected, more preferably one or more ortho-metallated complex compounds of one or more metal atoms selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and even more preferably act one or more ortho-metalated iridium complex compounds.

The dopant may use the compound represented by the following formula 101, but is not limited to it:

It applies that in formula 101
L is selected from the following structure 1 or 2;

R ₁₀₀ to R ₁₀₃ each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C3-C30) -cycloalkyl, a substituted or unsubstituted (C6-C30) -aryl, cyano , a substituted or unsubstituted (3 to 30-membered) heteroaryl or a substituted or unsubstituted (C1-C30) -alkoxy or R ₁₀₀ to R ₁₀₃ with one or more adjacent substituents to form a substituted or unsubstituted fused ring, e.g. B. substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuropyridine, a substituted or unsubstituted benzothienopyridine, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuroquinoline, a substituted or unsubstituted benzothienoquinoline or a substituted or unsubstituted benzothienoquinoline may be linked;
R ₁₀₄ to R ₁₀₇ each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C3-C30) -cycloalkyl, a substituted or unsubstituted (C6-C30) -aryl substituted (3- to 30-membered) heteroaryl, cyano or a substituted or unsubstituted (C1-C30) alkoxy or R ₁₀₄ to R ₁₀₇ with one or more adjacent substituents to form a substituted or unsubstituted fused ring, e.g. B. substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuropyridine or a substituted or unsubstituted benzothiene may be linked;
R ₂₀₁ to R ₂₁₁ each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30) -alkyl, a substituted or unsubstituted (C3-C30) -cycloalkyl or a substituted or unsubstituted (C6-C30) -aryl or can be linked to one or more adjacent substituents to form a substituted or unsubstituted ring; and
s is an integer from 1 to 3.

The specific examples of the dopant compound specifically include, but are not limited to, the following:

The following describes the organic electroluminescent device to which the above-mentioned organic electroluminescent compound or material is applied.

According to one embodiment, the organic electroluminescent device contains a first electrode, a second electrode and at least one organic layer which is arranged between the first electrode and the second electrode.

The compound of the present disclosure represented by Formula 1 may be contained in at least one layer constituting the organic electroluminescent device. According to one embodiment, the organic layer contains a hole transport layer and / or a light-emitting layer which comprises the organic electroluminescent compound according to the present disclosure. The hole transport layer and / or the light emitting layer consists exclusively of the organic electroluminescent compound of the present disclosure or at least two species of the organic electroluminescent compound of the present disclosure and may further comprise conventional materials contained in the organic electroluminescent material.

In addition, the organic layer may comprise a hole transport layer and a light emitting layer, and further comprise at least one layer selected from a hole injection layer, a hole auxiliary layer, an light emitting auxiliary layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, an electron blocking layer and an electron buffer layer, each layer can furthermore be made up of a plurality of layers. In addition, the organic layer can further comprise at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound, and furthermore at least one metal selected from the group consisting of metals of group 1, metals of Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides and organic metals of the d-transition elements of the periodic table or at least one complex compound comprising such a metal.

An organic electroluminescent material according to an embodiment can be used as a light emitting material for a white organic light emitting device. The white organic light emitting device has been proposed in various structures 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), blue (B) or yellowish-green (YG) light-emitting units. In addition, according to an embodiment, the organic electroluminescent material can also be applied to the organic electroluminescent device comprising a quantum dot (QD).

One of the first electrode and the second electrode can be an anode and the other can be a cathode; wherein the first electrode and the second electrode can each be designed as a transmissive conductive material, transflective conductive material or reflective conductive material. The organic electroluminescent device may be of a top emission type, a bottom emission type, or a double emission type according to the types of the material from which the first electrode and the second electrode are formed.

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. The hole injection layer can be used to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer be formed in multiple layers, it being possible for two compounds to be used simultaneously in each of the multiple layers. The hole injection layer can also be doped as a p-type dopant. The electron blocking layer may be disposed between the hole transport layer (or hole injection layer) and the light emitting layer, and restrict the excitons in the light emitting layer by blocking the overflow of electrons from the light emitting layer to prevent light emission leakage. The hole transport layer or the electron blocking layer can be formed in multiple layers, it being possible for a plurality of compounds to be used in each layer.

An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light emitting layer and the cathode. The electron buffer layer may be multilayered in order to control electron injection and improve the interface properties between the light emitting layer and the electron injection layer, and two compounds can be used simultaneously in each of the plural layers. The hole-blocking layer or the electron-transport layer can also have a multilayer design, it being possible for a plurality of compounds to be used in each layer. In addition, the electron injection layer can be doped as an n-type dopant.

The light-emitting auxiliary layer can be arranged between the anode and the light-emitting layer or between the cathode and the light-emitting layer. When the auxiliary light-emitting layer is arranged between the anode and the light-emitting layer, it can be used to promote hole injection and / or hole transport or to prevent electrodes from overflowing. When the auxiliary light-emitting layer is arranged between the cathode and the light-emitting layer, it can be used to promote electron injection and / or electron transport or to prevent holes from overflowing. In addition, the hole auxiliary layer may be disposed between the hole transport layer (or hole injection layer) and the light emitting layer and promote or block the hole transport rate (or the hole injection rate), whereby the charge balance can be controlled. When an organic electroluminescent device contains two or more hole transport layers, the hole transport layer further included can be used as the hole assist layer or the electron blocking layer. The auxiliary light-emitting layer, the auxiliary hole layer or the electron blocking layer can improve the efficiency and / or the service life of the organic electroluminescent device.

In the organic electroluminescent device of the present disclosure, preferably at least one layer (hereinafter “a surface layer”) selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer may be disposed on an inner surface of one or both of the electrodes. Specifically, a layer of chalcogenides (including oxides) of silicon and aluminum is preferably disposed on an anode surface of a layer of an electroluminescent medium, and a layer of halogenated metal or a metal oxide layer is preferably disposed on a cathode surface of a layer of electroluminescent medium. The operational stability for the organic electroluminescent device can be obtained by the surface layer. Preferred examples of the chalcogenide include SiO _x (1 _X 2), AlO x (1 X 1.5), SiON, SiAlON, etc .; the halogenated metal includes LiF, MgF ₂ , CaF ₂ , a rare earth fluoride, etc., and the metal oxide includes Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO and so on.

In addition, in the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant may be disposed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, making it easier to inject and transport electrons from the mixed region into an electroluminescent medium. Furthermore, the hole transport compound is oxidized to a cation, which makes it easier to inject and transport holes from the mixed region into the electroluminescent medium. Preferred examples of the oxidative dopant include. various Lewis acid and acceptor compounds, and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, a layer of reductive dopant can be used as a charge generating layer to fabricate an organic electroluminescent device that has two or more light emitting layers and that emits white light.

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.

In the following, the production method of compounds according to the present disclosure will be explained with reference to the synthesis method for a representative compound or the intermediate compound of the present disclosure in order to understand the present disclosure in detail.

[Example 1] Preparation of Compound C-34

Synthesis of compound 1-1

Compound A (20 g, 81.27 mmol), 4-iodo-1,1'-biphenyl (34 g, 121.90 mmol), copper powder (Cu) (2.6 g, 40.64 mmol), potassium carbonate ( K ₂ CO ₃ ) (22.5 g, 162.54 mmol) and 406 ml of 1,2-dichlorobenzene (1,2-DCB) were placed in a reaction vessel and stirred at 200 ° C. for 24 hours. After the completion of the reaction, the mixture of the organic layer was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed on a rotary evaporator. Thereafter, the residue was purified by column chromatography, whereby Compound 1-1 (19 g, yield: 59%) was obtained.

Synthesis of Compound C-34

Compound 1-1 (5.0 g, 12.55 mmol), di ([1,1'-biphenyl] -4-yl) amine (4.4 g, 13.81 mmol), tris (dibenzylidene acetone) dipalladium ( 0) (Pd ₂ (dba) ₃ ) (0.6 g, 0.63 mmol), tri-t-butylphosphine (P (t-Bu) ₃ ) (0.6 ml, 1.26 mmol), sodium tert-Butoxide (NaOt-Bu) (1.8 g, 18.83 mmol) and 63 ml of toluene were placed in a reaction vessel and refluxed for 1 hour. After the reaction mixture had cooled to room temperature, the solid was filtered off and washed with ethyl acetate. The remaining liquid was distilled under reduced pressure and purified by column chromatography to give Compound C-34 (2.1 g, yield: 26%). MG Fp. C-34 638.80 225 ° C

[Example 2] Preparation of Compound C-36

Compound 1-1 (3.0 g, 11.16 mmol), N- (1,1'-Biphenyl-4-yl) -9,9-dimethyl-9H-fluorene-2-amine (5.0 g, 12.28 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.56 mmol), P (t-Bu) ₃ (0.3 ml, 1.12 mmol), NaOt-Bu (1.6 g, 16.74 mmol) and 56 ml of toluene were placed in a reaction vessel and refluxed for 1 hour. After the reaction mixture had cooled to room temperature, the solid was filtered off and washed with ethyl acetate. The remaining liquid was distilled under reduced pressure and purified by column chromatography to give Compound C-36 (2 g, yield: 28%). MG Fp. C-36 678.86 168 ° C

In the following, the characteristics of an organic electroluminescent device comprising an organic electroluminescent compound will be explained in order to understand the present disclosure in detail.

[Device Examples 1 to 7] Manufacture of OLEDs comprising the organic electroluminescent compound according to the present disclosure

OLEDs have been fabricated that include the organic electroluminescent compound according to 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 and isopropanol and then stored in isopropanol ITO substrate mounted on a substrate holder of a vacuum vapor deposition apparatus, Compound HI-1 was placed in a cell of the vacuum vapor deposition apparatus, the pressure in the chamber of the apparatus was ^{adjusted to 10 -6} Torr, and an electric current was applied to the cell to generate the deposited material, thereby forming a first hole injection layer 80 nm thick on the ITO substrate, then compound HI-2 was deposited in another cell of the vacuum vapor deposition apparatus and an electric current was applied to the cell to apply the deposited material evaporate, creating a second hole injection layer with a thickness of 5 nm was formed on the first hole injection layer. Next, Compound HT-1 was added to another cell of the vacuum vapor deposition apparatus. Thereafter, an electric current was applied to the cell to evaporate the introduced material, whereby a first hole transport layer with a thickness of 10 nm was formed on the second hole injection layer. Then, the compound listed in the following Table 2 as the second hole transport material was introduced into another cell of the vacuum vapor deposition apparatus, and the introduced material was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer with a thickness of 30 nm on the first hole transport layer became. Then, after the formation of the hole injection layers and the hole transport layers, a light emitting layer was applied thereon using plural host materials as follows: Compound H-1 as a host was put into one cell of the vacuum vapor deposition apparatus, and Compound H-2 was put into another cell as a host . The two host materials were evaporated in a ratio of 2: 1 and at the same time the compound D-99 was introduced into another cell as a dopant. The dopant was doped in a doping amount of 10% by weight based on the rate of deposition of the light emitting layer to form a light emitting layer having a thickness of 40 nm on the hole transport layer. Next, Compounds ET-1 and EI-1 were added to another cell, evaporated at a rate of 1: 1, and deposited to form an electron transport layer with a thickness of 35 nm on the light-emitting layer. After Compound EI-1 was deposited as an electron injection layer with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 800 nm was deposited on the electron injection layer using another vacuum vapor deposition apparatus. This is how OLEDs were made.

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

An OLED was fabricated in the same manner as in Device Examples 1 to 7, except that Compound G'-1 was used as in a second hole transport layer.

Lichtemittierende Schicht

Elektronentransportschicht / Elektroneninjektionsschicht

The compounds used in Comparative Device Examples 1 to 7 and Comparative Example 1 are shown in detail in Table 1 below. [Table 1] Hole injection layer / hole transport layer

Light emitting layer

Electron transport layer / electron injection layer

The results of the drive voltage, current efficiency, power efficiency, external quantum efficiency and color coordinates at a luminance of 1000 nits for the organic electroluminescent device of Device Examples 1 to 7 and Comparative Example 1, which were manufactured as above, are in Table 2 below shown. [Table 2] Second host transport material Driver voltage (V) Power efficiency (Cd / A) Electricity efficiency (Lm / W) External quantum efficiency (%) Color coordinates CIE x y Device example 1 C-36 2.6 98.4 117.1 25.3 0.336 0.636 Device example 2 C-5 2.7 97.0 114.5 25.0 0.338 0.634 Device example 3 C-35 2.7 101.8 120.4 26.2 0.336 0.636 Device example 4 C-140 2.7 96.8 114.1 24.8 0.334 0.638 Device example 5 C-38 2.6 95.3 113.9 24.4 0.335 0.637 Device example 6 C-28 2.6 100.3 118.9 25.7 0.335 0.637 Device example 7 C-49 2.6 99.8 118.8 25.6 0.333 0.638 Comparative example 1 G'-1 2.7 93.0 110.3 23.9 0.338 0.634

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

• JP 5609256 B2 [0006]

Non-patent literature cited

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

Claims (8)

Organic electroluminescent compound represented by Formula 1 below:

where Ar ₁ to Ar ₃ each independently represent hydrogen, deuterium, 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 mono- or di- (C1-C30) -alkylamino, a substituted or unsubstituted mono- or di- (C6-C30) -arylamino or a substituted or unsubstituted (C1-C30) -alkyl- (C6- C30) -arylamino; L ₁ and L ₂ each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene; R ₁ and R ₂ 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, a substituted one or unsubstituted mono- or di- (C1-C30) -alkylamino, a substituted or unsubstituted mono- or di- (C6-C30) -arylamino or a substituted or unsubstituted (C1-C30) -alkyl- (C6-C30) - arylamino stand; A stands for an integer with a value from 1 to 4, b stands for an integer with a value from 1 to 3, c stands for an integer with a value of 1 or 2, with the proviso that if L _{2 represents} a single bond, c is 1; and when a, b and c are 2 or more, each of R ₁ , each of R _2, and each of -NAr ₂ Ar _{3 may be the} same or different. Organic electroluminescent compound according to Claim 1 , where formula 1 is represented by the following formula 2 or 3:

where Ar ₁ to Ar ₃ , L ₁ , L ₂ , R ₁ and R ₂ , a and b as in Claim 1 and L _{3 represents} a substituted or unsubstituted (C6-C30) -arylene or a substituted or unsubstituted (3 to 30-membered) heteroarylene. Organic electroluminescent compound according to Claim 1 , where Ar ₂ and Ar ₃ each independently represent one of the substituents selected from the following group 1:

where A1 to A3 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; and L stands for a substituted or unsubstituted (C6-C30) -arylene or a substituted or unsubstituted (3 to 30-membered) heteroarylene. Organic electroluminescent compound according to Claim 1 wherein Ar ₁ to Ar ₃ each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl; L ₁ and L ₂ each independently represent a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5- to 15-membered) heteroarylene; and R ₁ and R ₂ each independently represent hydrogen, a substituted or unsubstituted (C1-C6) alkyl, or a substituted or unsubstituted (C6-C12) aryl. Organic electroluminescent compound according to Claim 1 , wherein Ar ₁ to Ar ₃ each independently represent a (C6-C30) -aryl which is unsubstituted or substituted by at least one of (C1-C6) -alkyl and (C6-C12) -aryl, or a by (C6- C12) -aryl substituted or unsubstituted (5- to 20-membered) heteroaryl; L ₁ and L ₂ each independently represent a single bond or an unsubstituted (C6-C18) arylene; and R ₁ and R ₂ each independently represent hydrogen or unsubstituted (C6-C12) aryl, Organic electroluminescent device according to Claim 1 , wherein the compound represented by Formula 1 is selected from the group consisting of:

is selected. An organic electroluminescent device comprising the organic electroluminescent compound of Claim 1 . Organic electroluminescent device according to Claim 7 wherein the organic electroluminescent compound is contained in a hole transport layer and / or a light emitting layer.