Organic electroluminescent compound and organic electroluminescent device comprising the same

Abstract

The present disclosure relates to organic electroluminescent compounds and organic electroluminescent devices comprising the same. By comprising the organic electroluminescent compound according to the present disclosure, an organic electroluminescent device having good thermal stability, low driving voltage, high luminous efficiency, and / or improved lifespan characteristics can be provided.

Description

Technical Field

[0001] This disclosure relates to organic electroluminescent compounds and organic electroluminescent devices comprising the same. Background Technology

[0002] Electroluminescent (EL) devices are self-emissive display devices that offer advantages such as a wider viewing angle, a higher contrast ratio, and a faster response time. The first organic electroluminescent device was developed by Eastman Kodak in 1987 using small aromatic diamine molecules and aluminum complexes as materials for forming the luminescent layer (see Appl. Phys. Lett. 51, 913, 1987).

[0003] Organic light-emitting diodes (OLEDs) convert electrical energy into light by applying electricity to organic light-emitting materials, and typically include an anode, a cathode, and an organic layer formed between these two electrodes. The organic layer of an OLED can include hole injection layers, hole transport layers, hole auxiliary layers, light-emitting auxiliary layers, electron blocking layers, light-emitting layers, electron buffer layers, hole blocking layers, electron transport layers, and electron injection layers, etc. Materials used in the organic layer can be categorized according to their function as hole injection materials, hole transport materials, hole auxiliary materials, light-emitting auxiliary materials, electron blocking materials, light-emitting materials (including host materials and dopant materials), electron buffer materials, hole blocking materials, electron transport materials, and electron injection materials, etc. In OLEDs, holes from the anode and electrons from the cathode are injected into the light-emitting layer by applying a voltage, and high-energy excitons are generated through the recombination of holes and electrons. The organic light-emitting compound moves to an excited state by energy and emits light by the energy when the organic light-emitting compound returns from the excited state to the ground state.

[0004] The most important factor determining the luminous efficiency in OLEDs is the luminescent material. Luminescent materials are required to possess the following characteristics: high quantum efficiency, high electron and hole mobility, and uniformity and stability of the formed luminescent material layer. Based on emission color, luminescent materials are classified as blue, green, or red luminescent materials, and further include yellow or orange luminescent materials. Furthermore, in terms of functionality, luminescent materials can be divided into host materials and dopant materials. Recently, the urgent task is to develop OLEDs with high efficiency and long lifetime. In particular, considering the EL characteristics required for medium and large OLED panels, there is an urgent need to develop highly superior luminescent materials compared to conventional luminescent materials. For this purpose, as a solid-state solvent and energy emitter, the host material should preferably have high purity and a suitable molecular weight for deposition under vacuum. In addition, the material is required to have high glass transition temperature and pyrolysis temperature for thermal stability, high electrochemical stability for long lifetime, easy formability of amorphous thin films, good adhesion to adjacent layers, and non-migration between layers.

[0005] In addition, there is a need to develop materials with excellent thermal stability that can improve the performance of organic electroluminescent devices in hole transport layers, buffer layers, electron transport layers, etc. (such as driving voltage, luminous efficiency and lifetime characteristics). Summary of the Invention

[0006] Technical issues

[0007] The purpose of this disclosure is to provide an organic electroluminescent compound that effectively produces an organic electroluminescent device with excellent thermal stability, low driving voltage, high luminous efficiency, and / or improved lifetime characteristics.

[0008] Solution to the problem

[0009] Compounds with low glass transition temperatures (Tg) may cause morphological changes even at low temperatures, reducing charge mobility in thin films and degrading OLED performance. As a result of in-depth research, the inventors of this invention have discovered that the highly fused-ring compounds according to this disclosure, despite their low molecular weight, possess high glass transition temperatures (Tg), resulting in low driving voltage, high luminous efficiency, and / or improved lifetime characteristics, while providing good morphological stability. Specifically, the inventors of this invention have discovered that the above objectives can be achieved by organic electroluminescent compounds represented by Formula 1:

[0010]

[0011] in

[0012] Y represents -N(R1)-, -C(R2)(R3)-, -O-, or -S-;

[0013] X1 to X 12Each can be represented independently as N or CR4;

[0014] R1 represents -L-(Ar) a ;

[0015] L represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3- to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group.

[0016] Ar can independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, Substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or substituted or unsubstituted (C6-C30)aryl(3-membered to 30-membered)heteroarylamino;

[0017] R2 to R4 independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyl di( (C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino; or R2 and R3 may be connected to each other to form one or more rings, or at least two adjacent R4 may be connected to each other to form one or more rings; R2 and R3 may be the same or different, and each R4 may be the same or different;

[0018] The premise is that X9 and X 10Both indicate CR4, X9 and X 10 The R4 groups do not fuse together to form pyrrole rings, thiophene rings, or furan rings;

[0019] The (hypo)aryl group contains at least one heteroatom selected from B, N, O, S, Si, and P; and

[0020] a represents an integer of 1 or 2; when a is an integer of 2, each Ar can be the same or different.

[0021] Beneficial effects of the present invention

[0022] The organic electroluminescent compounds according to this disclosure can provide organic electroluminescent devices with low driving voltage, high luminous efficiency, and / or improved lifetime characteristics. Furthermore, or alternatively, the organic electroluminescent compounds according to this disclosure exhibit excellent thermal stability compared to other organic electroluminescent compounds with similar molecular weights. Detailed Implementation

[0023] This disclosure will be described in detail below. However, the following description is intended to explain this disclosure and is not intended to limit the scope of this disclosure in any way.

[0024] The term "organic electroluminescent compound" in this disclosure means a compound that can be used in an organic electroluminescent device and can be included, as needed, in any layer constituting the organic electroluminescent device.

[0025] The term "organic electroluminescent material" in this disclosure refers to a material that can be used in an organic electroluminescent device and may contain at least one compound. If desired, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting assist material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material, etc.

[0026] The organic electroluminescent material disclosed herein may contain at least one compound represented by Formula 1. The compound having Formula 1 may be contained in the luminescent layer, but is not limited thereto. In this case, the compound having Formula 1 may be contained as the host. Furthermore, the compound having Formula 1 may be contained in the electron transport region. The compound having Formula 1 may be contained in the electron buffer layer, but is not limited thereto.

[0027] In this document, the term "(C1-C30)alkylene" refers to a straight-chain or branched (alkylene)ene having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 10, and more preferably 1 to 6. The aforementioned alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. The term "(C3-C30)cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in the ring skeleton, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The aforementioned cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term "(3- to 7-membered)heterocyclic alkyl" refers to a cycloalkyl group having 3 to 7 ring skeleton atoms and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably from the group consisting of O, S, and N. The aforementioned heterocyclic alkyl groups may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene, tetrahydropyran, etc. The term "(C6-C30)aryl" refers to a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in its ring skeleton. The aforementioned ()aryl groups may be partially saturated and may contain a spirostructure. The aforementioned aryl groups may include phenyl, biphenyl, terphenyl, naphthyl, binatyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrene, phenylphenanthrene, anthracene, indole, benzo[a]phenanthrene, pyrene, tetraphenyl, perylene, etc. Aryl, naphthyl, fluoranthyl, spirodifluorenyl, spiro[fluorene-benzo[fluorene]]yl, etc. More specifically, aryl groups can include phenyl, 1-naphthyl, 2-naphthyl, 1-anthrayl, 2-anthrayl, 9-anthrayl, benzo[anthrayl], 1-phenanthyl, 2-phenanthyl, 3-phenanthyl, 4-phenanthyl, 9-phenanthyl, naphthyl, pyrene, 1- basal, 2- basal, 3- basal, 4- Base, 5- Base, 6- Benzyl, benzo[c]phenanthrene, benzo[g] 1-Benzophenanthryl, 2-Benzophenanthryl, 3-Benzophenanthryl, 4-Benzophenanthryl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[fluorenyl]fluorenyl, dibenzo[fluorenyl]fluorenyl, 2-biphenyl, 3-biphenyl, 4-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-tetraphenyl, 3-fluoranthyl, 4-fluoranthyl, 8-fluoranthyl, 9-fluoranthyl, benzo[fluoranthyl]fluorenthyl, o-tolyl, m-tolyl, p-tolyl, 2, 3-Dimethylbenzyl, 3,4-Dimethylbenzyl, 2,5-Dimethylbenzyl, mesitylene, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 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, etc.

[0028] The term "(3- to 30-membered) (hypo)aryl" refers to an aryl or aryl group having 3 to 30 ring skeleton atoms, preferably 5 to 30 ring skeleton atoms, and comprising at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The aforementioned (hypo)aryl group may be a monocyclic ring or a fused ring condensed with at least one benzene ring; it may be partially saturated; it may be a (hypo)aryl group formed by linking at least one heteroaryl group or an aryl group to a heteroaryl group via one or more single bonds; and it may contain a spirostructure. The aforementioned heteroaryl groups can include monocyclic heteroaryl groups, such as furanyl, thiophene, pyrrole, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetrazolyl, furazanyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc.; and fused-ring heteroaryl groups, such as benzofuranyl, benzothiophene, isobenzofuranyl, dibenzofuranyl, dibenzothiophene, benzonaphtho Thiophene, benzimidazolyl, benzothiazolyl, benziisothiazolyl, benziisooxazolyl, benzooxazolyl, isoindolyl, indolyl, indazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinolinyl, quinazolinyl, quinoxolinyl, benzoquinoxolinyl, carbazole, benzocarbazole, dibenzocarbazole, phenoxazinyl, phenanthidyl, benzom-dioxacyclopentenyl, naphridyl, benzofuran-pyrimidyl, benzothiophene-pyrimidyl, indol-pyrimidyl, indene-pyrimidyl, etc. More specifically, heteroaryl groups may include 1-pyrrolithyl, 2-pyrrolithyl, 3-pyrrolithyl, pyrazinyl, 2-pyridyl, 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-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl, 6-imidazopyridyl, 7-imidazopyridyl, 8-imidazopyridyl 3-pyridyl, 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-furanyl, 3-furanyl, 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-Quinolinyl, 3-Quinolinyl, 4-Quinolinyl, 5-Quinolinyl, 6-Quinolinyl7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolinyl, 8-isoquinolinyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, 4-carbazoleyl, 9-carbazoleyl, azacarbazole-1-yl, azacarbazole-2-yl, azacarbazole-3-yl, azacarbazole-4-yl, azacarbazole-5-yl, azacarbazole 6-yl, azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthidyl, 2-phenanthidyl, 3-phenanthidyl, 4-phenanthidyl, 6-phenanthidyl, 7-phenanthidyl, 8-phenanthidyl, 9-phenanthidyl, 10-phenanthidyl, 1-acridyl, 2-acridyl, 3-acridyl, 4-acridyl, 9-acridyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3- Thiopheneyl, 2-methylpyrrolidinyl, 2-methylpyrrolidinyl, 2-methylpyrrolidinyl, 2-methylpyrrolidinyl, 2-methylpyrrolidinyl, 3-methylpyrrolidinyl, 3-methylpyrrolidinyl, 3-methylpyrrolidinyl, 3-methylpyrrolidinyl, 3-methylpyrrolidinyl, 3-methylpyrrolidinyl, 2-tert-butylpyrrolidinyl, 3-(2-phenylpropyl)pyrrolidinyl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-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-dibenzothiopheneyl, 2-dibenzothiopheneyl, 3-dibenzothiopheneyl, 4-dibenzothiopheneyl, 1-siliconfluorenyl, 2-siliconfluorenyl, 3-siliconfluorenyl, 4-siliconfluorenyl, 1-germaniumfluorenyl, 2-germaniumfluorenyl, 3-germaniumfluorenyl, 4-germaniumfluorenyl, etc. "Halogens" include F, Cl, Br, and I.

[0029] Furthermore, "ortho (o-)," "meta (m-)," and "para (p-)" are prefixes that indicate the relative positions of the substituents, respectively. Ortho indicates that the two substituents are adjacent to each other, and for example, when the two substituents in a benzene derivative occupy positions 1 and 2, it is called ortho. Meta indicates that the two substituents are at positions 1 and 3, and for example, when the two substituents in a benzene derivative occupy positions 1 and 3, it is called meta. Para indicates that the two substituents are at positions 1 and 4, and for example, when the two substituents in a benzene derivative occupy positions 1 and 4, it is called para.

[0030] In this document, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or another functional group (i.e., a substituent). In this disclosure, the substituents of substituted ()alkylene, substituted ()aryl, substituted ()heteroaryl, substituted ()cycloalkylene, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted mono- or di-alkylamino, substituted mono- or di-arylamino, substituted alkylarylamino, and substituted arylheteroarylamino are each independently selected from at least one of the following groups: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; (C 1-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) heterocyclic alkyl; (C6-C30)aryloxy; (C6-C30) arylthio; unsubstituted or (3- to 30-membered) heteroaryl substituted with one or more (C6-C30) aryl groups; unsubstituted or substituted with (C1-C30) alkyl and (3- to 30-membered) aryl groups. At least one substituted (C6-C30) aryl group in the heteroaryl group; 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; unsubstituted or mono- or di-(C6-C30)arylamino substituted with one or more (C1-C30)alkyl groups; (C1-C30)alkyl(C6-C30)aryl aryl amino; unsubstituted or (C6-C30) aryl (3- to 30-membered) heteroaryl amino groups substituted with one or more (C6-C30) aryl groups; (C1-C30) alkyl carbonyl; (C1-C30) alkoxy carbonyl; (C6-C30) aryl carbonyl; di(C6-C30) arylboron carbonyl; di(C1-C30) alkylboron carbonyl; (C1-C30) alkyl(C6-C30) arylboron carbonyl; (C6-C30) aryl(C1-C30) alkyl; and (C1-C30) alkyl(C6-C30) aryl.According to one embodiment of this disclosure, each substituent is independently at least one selected from the group consisting of: deuterium; (C1-C20) alkyl; unsubstituted or (5- to 25-membered) heteroaryl substituted with one or more (C6-C25) aryl groups; unsubstituted or (C6-C25) aryl substituted with at least one of (C1-C20) alkyl and (3- to 20-membered) heteroaryl groups; amino; unsubstituted or (C1-C10) alkyl substituted mono- or di-(C6-C25) arylamino; and unsubstituted or (C6-C18) aryl (3- to 25-membered) heteroarylamino substituted with one or more (C6-C18) aryl groups. According to another embodiment of this disclosure, each substituent is independently at least one selected from the group consisting of: (C1-C10)alkyl; unsubstituted or (5- to 20-membered) heteroaryl substituted with one or more (C6-C18)aryl groups; unsubstituted or (C6-C18)aryl substituted with at least one of (C1-C10)alkyl and (5- to 20-membered) heteroaryl groups; di(C6-C18)arylamino substituted with one or more (C1-C10)alkyl groups; and (C6-C18)aryl(3- to 20-membered) heteroarylamino substituted with one or more (C6-C18)aryl groups. For example, each substituent may independently be at least one selected from the group consisting of: methyl, unsubstituted or substituted phenyl with one or more diphenyltriazine groups, naphthyl, biphenyl, dimethylfluorenyl, triazine substituted with one or more phenyl groups and / or one or more biphenyl groups, quinazolinyl substituted with one or more phenyl groups, quinoxalinyl substituted with one or more phenyl groups, dibenzofuranyl, dimethylfluorenylbiphenylamino, dimethylfluorenylphenylamino, phenylcarbazolylbiphenylamino, and phenylcarbazolylphenylamino.

[0031] In the formulas of this disclosure, a ring formed by the connection of adjacent substituents means that at least two adjacent substituents are connected or fused together to form a substituted or unsubstituted monocyclic or polycyclic (3-membered to 30-membered) alicyclic or aromatic ring, or a combination thereof; preferably, a substituted or unsubstituted monocyclic or polycyclic (3-membered to 26-membered) alicyclic or aromatic ring, or a combination thereof; and more preferably, an unsubstituted monocyclic or polycyclic (5-membered to 10-membered) aromatic ring. For example, the ring may be a benzene ring, an indole ring, an indole ring, a benzofuran ring, or a benzothiophene ring, etc. In addition, the ring may contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S.

[0032] In this document, each of the heteroaryl, heteroaryl, and heterocycloalkyl groups may independently contain at least one heteroatom selected from B, N, O, S, Si, and P. Furthermore, the heteroatom may be bonded to at least one of the following groups: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted dialkylsilyl, etc. (C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkylbis(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, and substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.

[0033] The organic electroluminescent compound represented by Formula 1 will be described in more detail below.

[0034] In Equation 1, Y represents -N(R1)-, -C(R2)(R3)-, -O-, or -S-; where R1 represents -L-(Ar). a .

[0035] In Equation 1, X1 to X 12 Each of them independently represents N or CR4. According to one embodiment of this disclosure, X1 to X 12 Each of them independently represents CR4. According to another embodiment of this disclosure, X1 to X... 12 Any one of them can represent N.

[0036] L represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene. According to one embodiment of this disclosure, L represents a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5- to 25-membered) heteroarylene. According to another embodiment of this disclosure, L represents a single bond, an unsubstituted (C6-C18) arylene, or an unsubstituted (5- to 20-membered) heteroarylene substituted with one or more (C1-C30) alkyl groups and / or one or more (C6-C30) aryl groups. For example, L can represent a single bond, phenylene, naphthylene, biphenylene, anthracene, pyridylene, pyrimidinylene, triazineylene, quinoxalinylene, quinoxalinylene, benzoquinoxalinylene, benzofuran-pyrimidinylene, benzothiophene-pyrimidinylene, indole-pyrimidinylene substituted with one or more phenyl groups, or inden-pyrimidinylene substituted with one or more methyl groups.

[0037] Ar can independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, Substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or substituted or unsubstituted (C6-C30)aryl (3- to 30-membered)heteroarylamino. According to one embodiment of this disclosure, Ar independently represents substituted or unsubstituted (C6-C25)aryl, substituted or unsubstituted (5- to 25-membered)heteroaryl, substituted or unsubstituted mono- or di-(C6-C25)arylamino, or substituted or unsubstituted (C6-C25)aryl (5- to 25-membered)heteroarylamino. According to another embodiment of this disclosure, Ar independently represents an unsubstituted (C6-C20) aryl group or a (C6-C18) aryl group substituted with one or more (C6-C18) aryl groups; an unsubstituted (5- to 25-aryl) heteroaryl group or a (C1-C10) alkyl group or a (C6-C18) aryl group substituted with at least one (C6- to 25-aryl) heteroaryl group; an unsubstituted (C6-C18) aryl(5- to 20-aryl) heteroarylamino group or a (C6-C18) aryl(5- to 20-aryl) heteroarylamino group or a (C6-C18) aryl(5- to 20-aryl) heteroarylamino group or a (C6-C18) aryl(5- to 20-aryl) heteroarylamino group substituted with one or more (C6-C18) aryl groups.Specifically, Ar can represent substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted anthracene, substituted or unsubstituted fluoranyl, substituted or unsubstituted triazine, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted benzofuranopyrimidinyl, substituted or unsubstituted indole-pyrimidinyl, substituted or unsubstituted indene-pyrimidinyl, substituted or unsubstituted benzothiophene-pyrimidinyl, substituted or unsubstituted acenaphthopyrimidinyl, substituted or unsubstituted pyrimidindole, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinone Azolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzo[a]quinoxalinyl, substituted or unsubstituted dibenzo[a]quinoxalinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzo[a]quinoxalinyl, substituted or unsubstituted isoquinoxalinyl, substituted or unsubstituted benzo[a]isoquinoxalinyl, substituted or unsubstituted benzo[a]thienyl, substituted or unsubstituted benzo[a]furanyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted carbazoleyl, substituted or unsubstituted dibenzo[a]thienyl, substituted or unsubstituted benzo[a]thienyl, substituted or unsubstituted dibenzo[a]furanyl, substituted or unsubstituted benzo[a]furanyl, substituted or unsubstituted naphthinyl, Substituted or unsubstituted benzothiazolinyl, substituted or unsubstituted phenanthimidazole, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylbiphenylamino, substituted or unsubstituted fluorenylphenylamino, substituted or unsubstituted fluorenylbiphenylamino, substituted or unsubstituted carbazoleylphenylamino, substituted or unsubstituted dibenzothiopheneylphenylamino, substituted or unsubstituted dibenzofuranylphenylamino, substituted or unsubstituted benzofuranopyrazinyl, substituted or unsubstituted benzofuranoquinoxalinyl, substituted or unsubstituted benzothiophenequinoxalinyl, substituted or unsubstituted benzothiophenequinoxalinyl, substituted or unsubstituted benzofuranoquinoxalinyl, substituted or unsubstituted Substituted benzothiophene-pyrazinyl, substituted or unsubstituted naphthofuran-pyrazinyl, substituted or unsubstituted naphthofuran-pyrimidinyl, substituted or unsubstituted naphthothiophene-pyrimidinyl, substituted or unsubstituted spiro[fluorene-indopyrimidinyl], substituted or unsubstituted spiro[fluorene-indopyrazinyl], substituted or unsubstituted acenaphthopyrazinyl, substituted or unsubstituted benzimidazotriazinyl, substituted or unsubstituted pyridininazolyl, substituted or unsubstituted dibenzoquinazoline, substituted or unsubstituted benzopyran-quinazoline, substituted or unsubstituted benzothioquinazoline, or substituted or unsubstituted dimethylbenzonaphthalene-intercalated diazaphenyl.For example, Ar can independently represent unsubstituted phenyl, unsubstituted naphthyl, unsubstituted biphenyl, unsubstituted terphenyl, substituted anthraquinyl, substituted pyrimidinyl, substituted triazine, substituted quinoxalinyl, substituted quinazolinyl, substituted naphthidyl, substituted benzoquinoxalinyl, unsubstituted dibenzofuranyl, substituted benzofuran-pyrimidinyl, substituted benzothiophene-pyrimidinyl, substituted acenaphthopyrimidinyl, substituted indolopyrimidinyl, substituted indenepyrimidinyl, unsubstituted diphenylamino, unsubstituted phenylbiphenylamino, substituted fluorenylphenylamino, substituted fluorenylbiphenylamino, substituted carbazolylphenylamino, substituted benzofuran-pyrazinyl, substituted benzofuran-quinoxalinyl Linyl, substituted benzothiophene-quinoxalinyl, substituted benzothiophene-quinoxalinyl, substituted benzofuran-quinoxalinyl, substituted benzothiophene-pyrazinyl, substituted naphthofuran-pyrazinyl, substituted or unsubstituted naphthothiophene-pyrazinyl, substituted or unsubstituted naphthofuran-pyrimidinyl, substituted or unsubstituted naphthothiophene-pyrimidinyl, substituted spiro[fluorene-indopyrimidinyl], substituted spiro[fluorene-indopyrazinyl], substituted or unsubstituted acenaphthopyrazinyl, unsubstituted benzimidazotriazinyl, unsubstituted pyridininazolyl, substituted dibenzoquinoxalinyl, unsubstituted benzopyran-quinoxalinyl, unsubstituted benzothiophene-quinoxalinyl, or unsubstituted dimethylbenzonaphthalene intercalation diazaphenyl. Substituted anthraceneyl, substituted pyrimidinyl, substituted triazineyl, substituted quinoxalinyl, substituted quinazolinyl, substituted naphthidyl, substituted benzoquinoxalinyl, substituted benzofuranopyrimidinyl, substituted benzothiophene-pyrimidinyl, substituted acenaphthyl, substituted indolopyrimidinyl, substituted indenepyrimidinyl, substituted fluorenylphenylamino, substituted fluorenylbiphenylamino, substituted carbazolylphenylamino, substituted benzofuranopyrazinyl, substituted benzofuranoquinoxalinyl, substituted benzothiophene-quinoxalinyl, substituted benzyl The substituents of benzo[thiophene]quinazolinyl, substituted benzo[furan]quinazolinyl, substituted benzo[thiophene]pyrazinyl, substituted naphtho[furan]pyrazinyl, substituted naphtho[thiophene]pyrazinyl, substituted naphtho[furan]pyrimidinyl, substituted naphtho[thiophene]pyrimidinyl, substituted spiro[fluorene-indopyrimidinyl]yl, substituted spiro[fluorene-indopyrazinyl]yl, substituted acenaphthene-pyrazinyl, and substituted dibenzo[quinazolinyl] can each independently be at least one selected from the group consisting of: methyl, phenyl, naphthyl, biphenyl, and dibenzofuranyl.

[0038] In Formula 1, R2 to R4 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or Unsubstituted (C1-C30)alkylbis(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or R2 and R3 may be linked together to form one or more rings, or at least two adjacent R4s may be linked together to form one or more rings. When X9 and X 10 Both indicate CR4, X9 and X 10 R4 in the formula do not fuse with each other to form pyrrole, thiophene, or furan rings. R2 and R3 can be the same or different, and each R4 can be the same or different.

[0039] According to one embodiment of this disclosure, R2 and R3 each independently represent a substituted or unsubstituted (C1-C20) alkyl, a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5-membered to 25-membered) heteroaryl; or R2 and R3 may be linked together to form a spirocycle. R2 and R3 may be the same or different. According to another embodiment of this disclosure, R2 and R3 each independently represent an unsubstituted (C1-C10) alkyl. For example, R2 and R3 may be methyl.

[0040] According to one embodiment of this disclosure, each of R4 independently represents hydrogen, deuterium, a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5- to 25-membered) heteroaryl; or at least two of adjacent R4 may be connected to each other to form one or more rings. According to another embodiment of this disclosure, each of R4 independently represents hydrogen; an unsubstituted or substituted (C6-C18) aryl, one or more (3- to 30-membered) heteroaryl, one or more di(C6-C18) arylamino, or a (C6-C20) aryl substituted with one or more (C6-C18) aryl (5- to 25-membered) heteroaryl; or an unsubstituted or substituted (5- to 20-membered) heteroaryl substituted with one or more (C6-C18) aryl; or two adjacent R4 may be connected to each other to form a substituted or unsubstituted monocyclic or polycyclic (3- to 30-membered) alicyclic or aromatic ring, or a combination thereof. The ring may contain at least one heteroatom selected from B, N, O, S, Si, and P. For example, each of R4 independently represents hydrogen, a substituted or unsubstituted phenyl group, a substituted naphthyl group, an anthraquinone group substituted with one or more phenyl groups, a triazine group substituted with one or more phenyl groups, a quinoxalinyl group substituted with one or more phenyl groups, or a quinazolinyl group substituted with one or more phenyl groups; or two adjacent R4 groups may be connected to each other to form an unsubstituted benzene ring, an indene ring substituted with one or more methyl groups, a substituted indole ring, an unsubstituted benzofuran ring, or an unsubstituted benzothiophene ring. The substituents of the substituted phenyl and substituted naphthyl groups may each independently be at least one group selected from the group consisting of: a triazine group substituted with one or more phenyl groups, a dimethylfluorenylbiphenylamino group, a dimethylfluorenylphenylamino group, a phenylcarbazolylbiphenylamino group, and a phenylcarbazolylphenylamino group. The substituents of the substituted indole ring may be at least one selected from the group consisting of: unsubstituted or substituted phenyl groups with one or more diphenyltriazine groups; triazine groups substituted with one or more phenyl groups and / or one or more biphenyl groups; quinazolinyl groups substituted with one or more phenyl groups; quinoxalinyl groups substituted with one or more phenyl groups; naphthyl groups; and dimethylfluorenyl groups.

[0041] In Equation 1, a represents an integer of 1 or 2; when a is an integer of 2, each Ar can be the same or different.

[0042] According to an embodiment of this disclosure, X1 to X in Formula 1 12 The two adjacent members are CR4, and the two adjacent R4 can be fused together in any of the forms of Formulas 2 to 6 to form a ring; and the ring can be present in one or more of a compound represented by Formula 1.

[0043]

[0044]

[0045] In equations 2 to 6, This indicates the bonding site between C and R4 in CR4.

[0046] In equations 2 to 6, X independently represents either N or CH. According to one embodiment of this disclosure, in any one of equations 2 to 6, all X can represent CH, or any one of X can represent N.

[0047] In Equation 5, R 10 This indicates hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl (C6... -C30) arylsilyl, substituted or unsubstituted (C1-C30) alkylbis(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino. According to one embodiment of this disclosure, R 10 This indicates a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-membered to 25-membered) heteroaryl group. According to another embodiment of this disclosure, R... 10 This indicates an unsubstituted (C6-C18) aryl group, or one substituted (C1-C10) alkyl group and / or one or more (5- to 20-membered) heteroaryl groups; or an unsubstituted (C6- to 25-membered) heteroaryl group, or one substituted (C6- to 25-membered) aryl group. For example, R 10 It can be phenyl; phenyl substituted with one or more diphenyltriazine groups; naphthyl; dimethylfluorenyl; pyridyl; triazine group substituted with one or more phenyl groups and / or one or more biphenyl groups; quinazolinyl group substituted with one or more phenyl groups; or quinoxalinyl group substituted with one or more phenyl groups.

[0048] In Equation 6, R 11 and R 12 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, or substituted or unsubstituted (C3-C30) cycloalkyl; or R 11 and R 12 They can be connected to each other to form one or more rings. According to one embodiment of this disclosure, R 11 and R12 Each can independently represent a substituted or unsubstituted (C1-C20) alkyl, a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5-membered to 25-membered) heteroaryl. R 11 and R 12 They can be the same or different. According to another embodiment of this disclosure, R... 11 and R 12 Each can be used independently to represent an unsubstituted (C1-C10) alkyl group. For example, R 11 and R 12 It can be methyl.

[0049] The compounds represented by Formula 1 can be specifically exemplified by the following compounds, but are not limited thereto.

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060] The compounds represented by Formula 1 according to this disclosure can be prepared by synthetic methods known to those skilled in the art and, for example, as shown in reaction schemes 1 and 2 below, but are not limited thereto.

[0061] [Reaction Scheme 1]

[0062]

[0063]

[0064] [Reaction Scheme 2]

[0065]

[0066] In reaction schemes 1 and 2, X1 to X 12 Y and R 10To R 12 It is defined as in equations 1, 5, and 6.

[0067] Although illustrative synthetic examples of compounds represented by Formula 1 have been described above, those skilled in the art will readily understand that they are all based on Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, H-mont mediated etherification reactions, Miyaura borylation reactions, Suzuki cross-coupling reactions, intramolecular acid-induced cyclization reactions, Pd(II) catalyzed oxidative cyclization reactions, Grignard reactions, Heck reactions, dehydration cyclization reactions, SN1 substitution reactions, SN2 substitution reactions, phosphine-mediated reductive cyclization reactions, etc., and that the above reactions are carried out even if substituents defined in Formula 1 above but not specified in the specific synthetic examples are bonded.

[0068] This disclosure provides an organic electroluminescent device comprising a compound represented by Formula 1. Specifically, the organic electroluminescent device may comprise a compound represented by Formula 1, and may further comprise at least one other organic electroluminescent compound.

[0069] Furthermore, this disclosure may provide an organic electroluminescent material comprising an organic electroluminescent compound having Formula 1, and an organic electroluminescent device comprising said organic electroluminescent material. The organic electroluminescent material may consist solely of the organic electroluminescent compound of this disclosure, or may further comprise conventional materials typically used in organic electroluminescent materials.

[0070] The organic electroluminescent device disclosed herein may include a first electrode, a second electrode, and at least one organic layer between the first and second electrodes. The organic layer may contain at least one organic electroluminescent compound having Formula 1. The organic layer may further contain at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds. Furthermore, the organic layer may further contain at least one metal selected from the group consisting of metals of Group 1, Group 2, transition metals of Period 4, transition metals of Period 5, lanthanides, and d-transition elements, or at least one complex compound containing said metal.

[0071] One of the first electrode and the second electrode can be an anode, and the other can be a cathode. The first electrode and the second electrode can each be formed from a transmissive conductive material, a semi-transmissive reflective conductive material, or a reflective conductive material. Depending on the type of material forming the first electrode and the second electrode, the organic electroluminescent device can be a top-emitting, bottom-emitting, or side-emitting type. The organic layer can include a light-emitting layer, and may further include at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a 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.

[0072] This disclosure may include a hole transport region between the anode and the light-emitting layer, and the hole transport region may include at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer. The hole injection layer, hole transport layer, hole auxiliary layer, light-emitting auxiliary layer, and electron blocking layer may each be a single layer, or multiple layers having two or more layers stacked thereon. The hole injection layer may be multilayered to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein two compounds may be used simultaneously in each of the multilayers. The electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may prevent light leakage by confining excitons within the light-emitting layer and blocking electrons from escaping from the light-emitting layer.

[0073] Furthermore, the hole transport region may include a p-type doped hole injection layer, a hole transport layer, and a light-emitting auxiliary layer. In this paper, a p-type doped hole injection layer refers to a hole injection layer doped with a p-type dopant. A p-type dopant is a material capable of imparting p-type semiconductor characteristics. P-type semiconductor characteristics refer to the properties of injecting or transporting holes at the HOMO level, i.e., the characteristics of a material with high hole conductivity.

[0074] This disclosure may include an electron transport region between the light-emitting layer and the cathode. The electron transport region may include at least one of a hole-blocking layer, an electron transport layer, an electron buffer layer, and an electron injection layer. The hole-blocking layer, electron transport layer, electron buffer layer, and electron injection layer may each be a single layer or multiple layers in which two or more layers are stacked. The electron injection layer may be further doped with one or more n-type dopants. The electron buffer layer may be multilayered to control electron injection and improve the interface properties between the light-emitting layer and the electron injection layer, wherein two compounds may be used simultaneously in each of the multilayers. The hole-blocking layer or electron transport layer may also be multilayered, wherein multiple compounds may be used in each of these layers.

[0075] A light-emitting auxiliary layer can be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When placed between the anode and the light-emitting layer, it can be used to promote hole injection and / or hole transport, or to prevent electron overflow. When placed between the cathode and the light-emitting layer, it can be used to promote electron injection and / or electron transport, or to prevent hole overflow. Furthermore, a hole auxiliary layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can effectively promote or block the hole transport rate (or hole injection rate), thereby enabling charge balance control. When an organic electroluminescent device includes two or more hole transport layers, the further included hole transport layers can serve as hole auxiliary layers or electron blocking layers. Light-emitting auxiliary layers, hole auxiliary layers, or electron blocking layers can improve the efficiency and / or lifetime of the organic electroluminescent device.

[0076] In the organic electroluminescent device disclosed herein, preferably, at least one layer selected from chalcogenide layers, metal halide layers, and metal oxide layers (hereinafter, "surface layer") may be placed on one or more inner surfaces of one or two electrodes. Specifically, it is preferred to place a silicon or aluminum chalcogenide (including oxide) layer on the anode surface of the electroluminescent dielectric layer, and preferably to place a metal halide layer or metal oxide layer on the cathode surface of the electroluminescent dielectric layer. The operational stability of the organic electroluminescent device can be achieved through the surface layer. Preferably, the chalcogenide includes SiO₂. X (1≤X≤2), AlO X (1≤X≤1.5), SiON, SiAlON, etc.; metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc.; and metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0077] In the organic electroluminescent device of this disclosure, a mixed region of electron transport compound and reducing dopant, or a mixed region of hole transport compound and oxidizing dopant, can be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anion, and thus it becomes easier to inject and transport electrons from the mixed region into the electroluminescent medium. Furthermore, the hole transport compound is oxidized to cation, and thus it becomes easier to inject and transport holes from the mixed region into the electroluminescent medium. Preferably, the oxidizing dopant includes various Lewis acids and acceptor compounds, and the reducing dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reducing dopant layer can be used as a charge-generating layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.

[0078] An organic electroluminescent compound represented by Formula 1 may be included in the emissive layer. When used in the emissive layer, the organic electroluminescent compound having Formula 1 may be included as a host material. Preferably, the emissive layer may further include at least one dopant. If desired, one or more other compounds besides the organic electroluminescent compound having Formula 1 may be included as a second host material. In this document, the weight ratio of the first host material to the second host material is 1:99 to 99:1. The second host material may be any known phosphorescent host.

[0079] The dopant included in the organic electroluminescent device of this disclosure may be at least one phosphorescent dopant or a fluorescent dopant, and preferably at least one phosphorescent dopant. The phosphorescent dopant material used in the organic electroluminescent device of this disclosure is not particularly limited, but may preferably be selected from metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) complexes, more preferably from ortho-metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) complexes, and even more preferably from ortho-metallized iridium complexes.

[0080] To form each layer of the organic electroluminescent device of this disclosure, dry film formation methods such as vacuum evaporation, sputtering, plasma and ion plating, or wet film formation methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating can be used. When a solvent is used in a wet film formation method, the film can be formed by dissolving or diffusing the material forming each layer into any suitable solvent (such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent can be any solvent in which the material forming each layer can dissolve or diffuse, and there are no problems with film-forming ability.

[0081] Furthermore, display systems or lighting systems can be produced using the organic electroluminescent compounds disclosed herein. Specifically, display systems, such as those for smartphones, tablets, laptops, PCs, TVs, or automobiles, or lighting systems, such as outdoor or indoor lighting systems, can be produced using the organic electroluminescent compounds disclosed herein.

[0082] The preparation methods of the compounds of this disclosure and the properties of the compounds will be explained in detail below with reference to representative compounds of this disclosure. However, this disclosure is not limited to the following examples.

[0083] Example 1: Preparation of compound C-11

[0084]

[0085] Synthesis of Compound 1-1

[0086] In a flask, 170 g of 1,8-dibromonaphthalene (594 mmol), 60 g of phenylboronic acid (492 mmol), 14.2 g of tetra(triphenylphosphine)palladium(0) (12.2 mmol), and 87 g of sodium carbonate (820 mmol) were dissolved in 1.6 L of toluene, 410 mL of ethanol, and 410 mL of water, and the mixture was refluxed at 120 °C for 3 hours. After the reaction was complete, the organic layer was separated with ethyl acetate, and the remaining water was dried over magnesium sulfate. The residue was separated by column chromatography to obtain 117 g of compound 1-1 (yield: 84%).

[0087] Synthesis of Compounds 1-2

[0088] In a flask, 117 g of compound 1-1 (254.2 mmol), 152 g of bis(pinacol)diboron (598 mmol), 14.5 g of bis(triphenylphosphine)palladium(II) dichloride (20.6 mmol), and 101 g of potassium acetate (1029 mmol) were dissolved in 2 L of 1,4-dioxane, and the mixture was refluxed at 120 °C for 3 hours. After the reaction was complete, the organic layer was separated with ethyl acetate, and the remaining water was dried over magnesium sulfate. The residue was separated by column chromatography to obtain 85 g of compound 1-2 (yield: 62.5%).

[0089] Synthesis of compounds 1-3

[0090] 85 g of compounds 1-2 (257 mmol), 79 g of 1-bromo-2-chloro-3-nitrobenzene (334 mmol), 17.8 g of tetra(triphenylphosphine)palladium(0) (15.4 mmol), 30.8 g of sodium hydroxide (772 mmol), 850 mL of tetrahydrofuran, and 386 mL of water were added to a flask, and the mixture was refluxed at 120 °C for 24 hours. After the reaction was complete, the organic layer was separated with ethyl acetate, and the remaining water was removed by using magnesium sulfate. The residue was separated by column chromatography to obtain 41 g of compounds 1-3 (yield: 45%).

[0091] Synthesis of compounds 1-4

[0092] 45 g of compounds 1-3 (125 mmol), 2.87 g of palladium acetate (12.7 mmol), 7.4 g of tricyclohexylphosphine tetrafluoroborate (20.0 mmol), 65.4 g of cesium carbonate (200 mmol), and 822 mL of dimethylacetamide were added to a flask, and the mixture was stirred under reflux for 1 hour. After the reaction was complete, the organic layer was extracted with ethyl acetate, and the remaining water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 39.4 g of compounds 1-4 (yield: 97%).

[0093] Synthesis of compounds 1-5

[0094] In a flask, 39.4 g of compounds 1-4 (121.8 mmol) and 91.7 g of triphenylphosphine (349 mmol) were dissolved in 1.2 L of dichlorobenzene, and the mixture was refluxed at 200 °C for 24 hours. After the reaction was complete, the solvent was removed by distillation under reduced pressure. The residue was separated by column chromatography to obtain 18.5 g of compounds 1-5 (yield: 70%).

[0095] Synthesis of compound C-11

[0096] In a flask, 5 g of compound 1-5 (17.1 mmol), 5.03 g of 2-chloro-3-phenylquinoxaline (20.8 mmol), 16.7 g of potassium carbonate (121.1 mmol), and 105 mg of dimethylaminopyridine (0.85 mmol) were dissolved in 100 mL of dimethylformamide, and the mixture was stirred under reflux for 24 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, and the remaining water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 2.1 g of compound C-11 (yield: 25%).

[0097] compound MW Tg MP C-11 495.59 123.07℃ 227℃

[0098] Example 2: Preparation of compound C-6

[0099]

[0100] In a flask, 5 g of compound 1-5 (17.1 mmol), 10 g of compound 2-1 (25.7 mmol), 781 mg of tris(dibenzylacetone)dipalladium(0) (0.85 mmol), 704 mg of SPhos (1.71 mmol), and 5 g of sodium tert-butoxide (52 mmol) were dissolved in 86 mL of xylene, and the mixture was stirred under reflux for 3 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, and the residual water was removed. The residue was dried and separated by column chromatography to obtain 4.6 g of compound C-6 (yield: 45%).

[0101] compound MW Tg MP C-6 598.71 131.42℃ 310℃

[0102] Example 3: Preparation of compound C-48

[0103]

[0104] In a flask, 4 g of compound 1-5 (13.72 mmol), 4.2 g of 3-bromo-1,1':2',1”-terphenyl (13.72 mmol), 620 mg of tris(dibenzylacetone)dipalladium(0) (0.686 mmol), 560 mg of SPhos (1.372 mmol), and 4 g of sodium tert-butoxide (41.18 mmol) were dissolved in 90 mL of xylene, and the mixture was stirred under reflux for 3 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, and the remaining water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 4 g of compound C-48 (yield: 56.6%).

[0105] compound MW Tg MP C-48 519.65 103.85℃ 226.8℃

[0106] The characteristics of organic electroluminescent devices (OLEDs) comprising compounds according to the present disclosure will be explained in detail below. However, the following examples only illustrate the characteristics of OLEDs according to the present disclosure, and the present disclosure is not limited to these examples.

[0107] Apparatus Example 1: Production of OLEDs containing a compound according to the present disclosure in an electron buffer layer

[0108] OLEDs were produced using organic electroluminescent compounds according to this disclosure. A transparent indium tin oxide (ITO) thin film (10 Ω / sq) (GEOMATEC CO.,LTD., Japan) on a glass substrate used for the OLED was subjected to ultrasonic washing sequentially with acetone, ethanol, and distilled water, and then stored in isopropanol. The ITO substrate was then mounted on a substrate holder in a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a chamber of the vacuum vapor deposition apparatus, and the pressure in the chamber was then controlled to 10 Ω / sq.-6 The process involves applying current to a chamber to evaporate the introduced material, thereby forming a first hole injection layer with a thickness of 60 nm on the ITO substrate. Next, compound HI-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying current to the chamber, thereby forming a second hole injection layer with a thickness of 5 nm on the first hole injection layer. Then, compound HT-1 is introduced into a chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying current to the chamber, thereby forming a first hole transport layer with a thickness of 20 nm on the second hole injection layer. Then, compound HT-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying current to the chamber, thereby forming a second hole transport layer with a thickness of 5 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer is formed thereon as follows: compound BH-3 is introduced as the host into one chamber of the vacuum vapor deposition apparatus, and compound BD is introduced as a dopant into another chamber. Two materials were evaporated and a dopant was deposited at a dopant concentration of 2 wt% based on the total amount of the host and dopant to form a 20 nm thick emissive layer on the second hole transport layer. Next, compound C-6 was deposited on the emissive layer to form a 5 nm thick electron buffer layer. Then, compounds ET-1 and EI-1 were introduced into two additional chambers and evaporated at a 1:1 rate to form a 30 nm thick electron transport layer on the electron buffer layer. After depositing compound EI-1 on the electron transport layer as a 2 nm thick electron injection layer, an 80 nm thick Al cathode was deposited on the electron injection layer using another vacuum vapor deposition apparatus. Thus, an OLED was produced.

[0109] As a result, based on a brightness of 2,000 nits, the shortest time it takes for the brightness to decrease from 100% to 90% is 187 hours.

[0110] Comparative Example 1: Producing OLEDs without any electron buffer layer

[0111] Except for evaporating compounds ET-1 and EI-1 at a 1:1 rate to form an electron transport layer with a thickness of 35 nm on the light-emitting layer, the OLED was produced in the same manner as in Device Example 1, as a device without an electron buffer layer.

[0112] As a result, based on a brightness of 2,000 nits, the shortest time it takes for the brightness to decrease from 100% to 90% is 128 hours.

[0113] The inventors of this invention have demonstrated that the lifetime of OLEDs is improved by introducing a separate electron buffer layer, in addition to the electron injection layer and the electron transport layer, to control the electron balance in the emissive layer, and by including the compounds disclosed herein in the electron buffer layer. When the bulk LUMO (lowest unoccupied molecular orbital) energy level of the emissive layer is formed at approximately -1.629 eV and the LUMO energy level of the electron transport layer is formed at approximately -1.888 eV, over-injected electrons into the emissive layer cause degradation at the interface between the hole transport layer and the emissive layer, leading to a reduced lifetime. To address this degradation, the inventors of this invention have incorporated the compounds of this disclosure, having a LUMO energy level of approximately -1.983 eV, between the emissive layer and the electron transport layer. As a result, the inventors of this invention have demonstrated that electron injection can be effectively controlled, thereby improving the lifetime of OLEDs. By including the compounds disclosed herein, the lifetime performance of blue organic light-emitting devices can be improved. Therefore, blue organic light-emitting devices can exhibit competitive performance, maintaining a balance with the lifetime performance of red and green organic light-emitting devices, and are thus expected to be suitable for various fields and displays.

[0114] Apparatus Examples 2-1 and 2-2: Production of OLEDs Containing Compounds According to the Present Disclosure in the Emitting Layer

[0115] OLEDs were produced using organic electroluminescent compounds according to this disclosure. A transparent indium tin oxide (ITO) thin film (10 Ω / sq) (GEOMATEC CO.,LTD., Japan) on a glass substrate used for the OLED was subjected to ultrasonic washing sequentially with acetone, ethanol, and distilled water, and then stored in isopropanol. The ITO substrate was then mounted on a substrate holder in a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a chamber of the vacuum vapor deposition apparatus, and the pressure in the chamber was then controlled to 10 Ω / sq. -6The introduced material is then evaporated by applying current to the chamber, forming a first hole injection layer with a thickness of 80 nm on the ITO substrate. Next, compound HI-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and evaporated by applying current to the chamber, forming a second hole injection layer with a thickness of 5 nm on the first hole injection layer. Then, compound HT-1 is introduced into a chamber of the vacuum vapor deposition apparatus, and evaporated by applying current to the chamber, forming a first hole transport layer with a thickness of 10 nm on the second hole injection layer. Then, compound HT-3 is introduced into another chamber of the vacuum vapor deposition apparatus, and evaporated by applying current to the chamber, forming a second hole transport layer with a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer is formed thereon as follows: the compound shown in Table 1 as the first host is introduced as the host into one chamber of the vacuum vapor deposition apparatus, and compound D-1 is introduced as a dopant into another chamber. Two materials were evaporated at different rates, and a dopant was deposited at a dopant concentration of 3 wt% based on the total amount of the host and dopant to form a 40 nm thick light-emitting layer on the second hole transport layer. Next, compounds ET-1 and EI-1 were introduced into two additional chambers and evaporated at a 1:1 ratio to form an electron transport layer with a 35 nm thick on the light-emitting layer. After depositing compound EI-1 as a 2 nm thick electron injection layer on the electron transport layer, an 80 nm thick Al cathode was deposited on the electron injection layer using another vacuum vapor deposition apparatus. Thus, an OLED was produced.

[0116] Apparatus Examples 2-3: Production of OLEDs containing compounds according to the present disclosure in the light-emitting layer

[0117] Except that the first and second host compounds shown in Table 1 below are introduced as hosts into two chambers of the vacuum vapor deposition apparatus, and compound D-1 is introduced into another chamber, and the two host materials are evaporated at a 1:1 rate while the dopant material is evaporated at different rates, and the dopant is deposited based on a doping amount of 3 wt% of the total amount of host and dopant to form the light-emitting layer, the OLED is produced in the same manner as in apparatus example 2-1.

[0118] Comparative Example 2: Production of OLEDs containing conventional compounds in the light-emitting layer

[0119] The OLED is produced in the same manner as in Device Example 2-1, except that compound A is used as the main body of the light-emitting layer.

[0120] Table 1 below provides the driving voltage of the OLEDs produced in Device Examples 2-1 to 2-3 and Comparative Example 2 at a brightness of 1,000 nits, and the time (lifetime; T95) taken for the brightness to decrease from 100% to 95% at a brightness of 5,000 nits.

[0121] [Table 1]

[0122]

[0123] As can be seen from Table 1, compared with conventional OLEDs, OLEDs containing compounds according to this disclosure as host materials exhibit lower driving voltages and longer lifetime characteristics.

[0124] The compounds used in the apparatus examples and comparative examples are shown in Table 2 below.

[0125] [Table 2]

[0126]

Claims

1. An organic electroluminescent compound, represented by formula 1: ----- (1) in Y represents -N(R1)-; X1 to X 12 Each CR4 is represented independently; R1 represents -L-(Ar) a ; L represents a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted terphenylene; Ar independently represents substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted triazine, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or substituted or unsubstituted terpinenyl. The substituents of the substituted phenyl, substituted phenylene, substituted biphenyl, substituted biphenylene, substituted terphenyl, and substituted terphenylene are each independently selected from at least one of the following groups: deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl. The substituents of the substituted triazine, substituted quinazolinyl, substituted quinoxalinyl, and substituted terpenoid are each independently selected from at least one of the following groups: deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, and terphenyl. R4 can independently represent hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, or tert-butyl; and each R4 can be the same or different; and a represents an integer of 1 or 2; when a is an integer of 2, each Ar can be the same or different.

2. The organic electroluminescent compound according to claim 1, wherein, L represents a single bond; Ar represents a substituted quinazolinyl group, a substituted quinoxalinyl group, or a substituted terpineyl group; and The substituents of the substituted quinazolinyl group, the substituted quinoxalinyl group, and the substituted cyclophosphinyl group are each independently phenyl.

3. The organic electroluminescent compound according to claim 1, wherein, L indicates a deuterated or unsubstituted phenylene; Ar represents a substituted triazine group; and The substituent of the substituted triazine group is phenyl.

4. The organic electroluminescent compound according to claim 1, wherein, L indicates a deuterated or unsubstituted phenylene; Ar represents deuterated or unsubstituted biphenyl.

5. The organic electroluminescent compound according to claim 1, wherein, The compound represented by Formula 1 is selected from the group consisting of the following compounds: 。 6. An organic electroluminescent material comprising the organic electroluminescent compound according to claim 1.

7. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.

8. The organic electroluminescent device according to claim 7, wherein, The organic electroluminescent compound is contained in at least one of the light-emitting layer and the electron transport region.

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