JP2022538472A - Novel compound and its application, and organic electroluminescence device using this compound - Google Patents

Abstract

A novel organic compound, its application, and an organic electroluminescence device using this compound, the compound has a structure represented by the following formula (1-1), (1-2), or (1-3). TIFF2022538472000092.tif58166 (Y1, Y2 and Y3 are each independently selected from B; X1, X2 and X3 are each independently selected from N; X4, X5 and X6 are each independently single bonds; or CR, wherein R is a substituted or unsubstituted C1-C30 linear alkyl group, C3-C30 cycloalkyl group, C1-C30 haloalkyl group, C1-C30 alkoxy group, C2-C30 alkenyl C3-C30 alkynyl group, C6-C60 monocyclic aryl group, C6-C60 condensed ring aryl group, C6-C60 aryloxy group, C5-C60 monocyclic heteroaryl group or C5-C60 condensed When this compound is used as a light-emitting layer material in an OLED device, it exhibits excellent device performance and stability. Also provided are organic electroluminescent devices using the compounds described above. [Selection figure] None

Description

The present invention relates to novel compounds and also to applications of such compounds, as well as organic light-emitting devices using such compounds.

Organic electroluminescent devices (OLEDs) are devices with a sandwich-like structure, comprising positive and negative electrode film layers and an organic functional material layer sandwiched between the electrode film layers. OLED devices have advantages such as high brightness, fast response, wide field of view, simple process, flexibility, etc., and are attracting attention in new display technology fields and new lighting technology fields. At present, this technology is widely applied to the display panels of new lighting equipment, smartphones, tablets and other products, and has further expanded into the application fields of large display products such as televisions. display technology.

With the development of OLEDs in the two fields of lighting and display, research into their core materials has also received more attention. This is the result of optimization combination. In order to produce OLED light-emitting devices with lower driving voltage, higher luminous efficiency and longer device usage life, and to achieve improved performance of OLED devices, it is necessary to innovate OLED device structures and manufacturing processes. In addition, there is also a need to research and innovate photoelectric functional materials in OLED devices, thereby producing functional materials with higher performance. Based on this, the OLED material industry has been working on developing new organic electroluminescent materials in order to achieve low start-up voltage, high luminous efficiency and better service life of the devices.

In the selection of OLED materials, singlet emitting fluorescent materials have good lifetime and low price, but low efficiency. Although triplet emitting phosphorescent materials have high efficiency, they are expensive and the lifetime problem of blue light materials has not been resolved. Adachi of Kyushu University, Japan proposed a new organic light emitting material, namely thermally activated delayed fluorescence (TADF) material. Because the singlet-triplet energy gap (ΔEST) of such materials is very small (<0.3 eV), triplet excitons can become singlet excitons by reverse intersystem crossing (RISC) and emit light. , the internal quantum efficiency of the device can reach 100%.

In the prior art, a compound with a new structure was designed with the strategy of "multi-resonance-induced thermally activated delayed fluorescence (MR-TADF)". A polycyclic aromatic compound formed by connecting multiple aromatic rings with atoms and nitrogen atoms is designed, that is, a rigid molecular system containing special boron (B) and nitrogen (N) atoms (the following formula ( A), where Y ¹ is B, and X ¹ and X ² are each independently NR), such thermally activated delayed fluorescent molecules exhibit high radiative transition rates and high color purity. , but the large HOMO-LUMO overlap results in a large material singlet-triplet energy difference (ΔEst), resulting in severe device efficiency roll-off. In addition, there is room for further improvement in the half-value width of the material, up to the demand for practical use.

式（１ー１）、（１ー２）または（１ー３）において、
Ｙ^１、Ｙ^２及びＹ^３はそれぞれ独立してＢから選択され、
Ｘ^１、Ｘ^２及びＸ^３はそれぞれ独立してＮから選択され、
ｍ、ｎ及びｐはそれぞれ独立して０または１から選択され、
Ｘ^４、Ｘ^５及びＸ^６はそれぞれ独立しては単結合またはＣＲから選択され、Ｒは置換若しくは無置換の、Ｃ１ーＣ３０の鎖状アルキル基、Ｃ３ーＣ３０のシクロアルキル基、Ｃ１ーＣ３０のハロアルキル基、Ｃ１ーＣ３０のアルコキシ基、Ｃ２ーＣ３０のアルケニル基、Ｃ３ーＣ３０のアルキニル基、Ｃ６ーＣ６０の単環アリール基、Ｃ６ーＣ６０の縮合環アリール基、Ｃ６ーＣ６０のアリールオキシ基、Ｃ５ーＣ６０の単環ヘテロアリール基またはＣ５ーＣ６０の縮合環ヘテロアリール基のうちの一種から選択され、 Chinese patent application 107851724 Chinese Patent Application No. 108431984 In order to solve the above technical problems, the present invention provides a novel thermally activated delayed fluorescent material that can be applied in the field of organic electroluminescence. Such an organic compound of the present invention is represented by the following general formula (1-1), (1-2) or (1-3).

In formula (1-1), (1-2) or (1-3),
Y ¹ , Y ² and Y ³ are each independently selected from B;
X ¹ , X ² and X ³ are each independently selected from N;
m, n and p are each independently selected from 0 or 1;
X ⁴ , X ⁵ and X ⁶ are each independently selected from a single bond or CR, R is a substituted or unsubstituted C1-C30 linear alkyl group, a C3-C30 cycloalkyl group, a C1-C30 haloalkyl group, C1-C30 alkoxy group, C2-C30 alkenyl group, C3-C30 alkynyl group, C6-C60 monocyclic aryl group, C6-C60 condensed ring aryl group, C6-C60 aryloxy group , a C5-C60 monocyclic heteroaryl group or a C5-C60 condensed ring heteroaryl group,

R ¹ to R ²⁰ are each independently hydrogen, deuterium, substituted or unsubstituted halogen, C1 to C30 chain alkyl group, C3 to C30 cycloalkyl group, C1 to C10 alkoxy group, C1 to C10 thioalkoxy group, carbonyl group, carboxyl group, nitro group, cyano group, amino group, silicon group, C6-C30 arylamino group, C3-C30 heteroarylamino group, C6-C60 monocyclic aryl group, C6 -C60 condensed ring aryl group, C6-C60 aryloxy group, C5-C60 monocyclic heteroaryl group or C5-C60 condensed ring heteroaryl group, and R ¹ to R ²⁰ two groups adjacent to each other are bonded to form one of a C5-C30 5- or 6-membered aryl ring and a C5-C30 5- or 6-membered heteroaryl ring together with the adjacent benzene ring, and at least one hydrogen in the formed ring is a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C60 monocyclic aryl group, a C6-C60 condensed ring aryl group, or a C6-C60 aryl oxy group, C5-C60 monocyclic heteroaryl group, C5-C60 condensed ring heteroaryl group, halogen, C1-C30 chain alkyl group, C3-C30 cycloalkyl group, C1-C10 alkoxy group, C1 may be substituted with any one of a C10 thioalkoxy group, a carbonyl group, a carboxyl group, a nitro group, a cyano group, and an amino group;

R ²¹ is hydrogen, deuterium, or substituted or unsubstituted halogen, C1-C30 chain alkyl group, C3-C30 cycloalkyl group, C1-C10 alkoxy group, C1-C10 thioalkoxy group, carbonyl; group, carboxyl group, nitro group, cyano group, amino group, C6-C30 arylamino group, C3-C30 heteroarylamino group, C6-C60 monocyclic aryl group, C6-C60 condensed ring aryl group, C6- selected from one of a C60 aryloxy group, a C5-C60 monocyclic heteroaryl group or a C5-C60 condensed ring heteroaryl group;

When the above groups have substituents, the substituents are each independently deuterium, halogen, cyano group, C1-C30 chain alkyl group, C3-C30 cycloalkyl group, C1-C10 alkoxy group, C6 ∼C30 arylamino group, C3-C30 heteroarylamino group, C6-C30 aryl group, C3-C30 heteroaryl group.

式（２ー１）、（２ー２）または（２ー３）において、Ｒ^１～Ｒ^２１はそれぞれ独立して請求項１と同じ限定範囲を有する。
よりさらに好ましくは、上記の各一般式において、
前記Ｒ^１～Ｒ^２１はそれぞれ独立して水素、重水素、または置換若しくは無置換の、メチル基、エチル基、ｎープロピル基、イソプロピル基、ｎーブチル基、イソブチル基、ｓｅｃーブチル基、ｔーブチル基、２ーメチルブチル基、ｎーペンチル基、ｓｅｃーペンチル基、シクロペンチル基、ネオペンチル基、ｎーヘキシル基、シクロヘキシル基、ネオヘキシル基、ｎーヘプチル基、シクロヘプチル基、ｎーオクチル基、シクロオクチル基、２ーエチルヘキシル基、トリフルオロメチル基、ペンタフルオロエチル基、２，２，２ートリフルオロエチル基、フェニル基、ナフチル基、アントラニル基、ベンゾアントラニル基、フェナントリル基、ベンゾフェナントリル基、ピレニル基、クリセニル基、ペリレニル基、フルオランテニル基、テトラセン基、ペンタセン基、ベンゾピレニル基、ビフェニル基、アゾフェニル基、テルフェニル基、トリポリフェニル基、p-クオターフェニル、フルオレニル基、スピロビフルオレニル基、ジヒドロフェナントリル基、ジヒドロピレニル基、テトラヒドロピレニル基、シスまたはトランスインデノフルオレニル基、トリポリインデニル基、イソトリポリインデニル基、スピロトリポリインデニル基、スピロイソトリポリインデニル基、フラニル基、ベンゾフラニル基、イソベンゾフラニル基、ジベンゾフラニル基、チエニル基、ベンゾチエニル基、イソベンゾチエニル基、ジベンゾチエニル基、ピロリル基、イソインドリル基、カルバゾリル基、インデノカルバゾリル基、ピリジル基、キノリル基、イソキノリル基、アクリジニル基、フェナントリジニル基、ベンゾー５，６ーキノリル基、ベンゾー６，７ーキノリル基、ベンゾー７，８ーキノリル基、ピラゾリル基、インダゾリル基、イミダゾリル基、ベンゾイミダゾリル基、ナフトイミダゾリル基、フェナントロイミダゾリル基、ピリドイミダゾリル基、ピラジノイミダゾリル基、キノキサリノイミダゾリル基、オキサゾリル基、ベンゾオキサゾリル基、ナフトオキサゾリル基、アントラオキサゾリル基、フェナントロオキサゾリル基、１，２ーチアゾリル基、１，３ーチアゾリル基、ベンゾチアゾリル基、ピリダジニル基、ベンゾピリダジニル基、ピリミジニル基、ベンゾピリミジニル基、キノキサリニル基、１，５ージアザアントラニル基、２，７ージアザピレニル基、２，３ージアザピレニル基、１，６ージアザピレニル基、１，８ージアザピレニル基、４，５ージアザピレニル基、４，５，９，１０ーテトラアザペリレニル基、ピラジニル基、フェナジニル基、フェノチアジニル基、ナフチリジニル基、アザカルバゾリル基、ベンゾカルボリニル基、フェナントロリニル基、１，２，３ートリアゾリル基、１，２，４ートリアゾリル基、ベンゾトリアゾリル基、１，２，３ーオキサジアゾリル基、１，２，４ーオキサジアゾリル基、１，２，５ーオキサジアゾリル基、１，２，３ーチアジアゾリル基、１，２，４ーチアジアゾリル基、１，２，５ーチアジアゾリル基、１，３，４ーチアジアゾリル基、１，３，５ートリアジニル基、１，２，４ートリアジニル基、１，２，３ートリアジニル基、テトラゾリル基、１，２，４，５ーテトラジニル基、１，２，３，４ーテトラジニル基、１，２，３，５ーテトラジニル基、プリニル基、プテリジニル基、インドリジニル基、ベンゾチアジアゾリル基、９，９ージメチルアクリジニル基、（ポリ）ハロゲン化ベンゼン、（ポリ）シアノベンゼン、（ポリ）トリフルオロメチルベンゼン、トリアリールアミノ基、アダマンタン、フルオロフェニル基、メチルフェニル基、トリメチルフェニル基、シアノフェニル基、テトラヒドロピロール、ピペリジン、メトキシ基、ケイ素基のうちの一種から選択され、または前記の二種の置換基の組み合わせから選択される。 More preferably, in formula (1-1), (1-2) or (1-3), at least one of m, n and p is 0, or at least one of m, n and p One is 1, or m is 0, n and p are both 1, or m is 1, n and p are both 0.
More preferably, the compounds of the general formula of the present invention are represented by the following formulas (2-1) to (2-3).

In formula (2-1), (2-2) or (2-3), R ¹ to R ²¹ each independently have the same limiting range as in claim 1.
Even more preferably, in each of the above general formulas,
Each of R ¹ to R ²¹ is independently hydrogen, deuterium, or a substituted or unsubstituted methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, or t-butyl group. , 2-methylbutyl group, n-pentyl group, sec-pentyl group, cyclopentyl group, neopentyl group, n-hexyl group, cyclohexyl group, neohexyl group, n-heptyl group, cycloheptyl group, n-octyl group, cyclooctyl group, 2-ethylhexyl group, trifluoromethyl group, pentafluoroethyl group, 2,2,2-trifluoroethyl group, phenyl group, naphthyl group, anthranyl group, benzoanthranyl group, phenanthryl group, benzophenanthryl group, pyrenyl group, chrysenyl group, perylenyl group, fluoranthenyl group, tetracene group, pentacene group, benzopyrenyl group, biphenyl group, azophenyl group, terphenyl group, tripolyphenyl group, p-quaterphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenanthryl a dihydropyrenyl group, a tetrahydropyrenyl group, a cis or transindenofluorenyl group, a tripolyindenyl group, an isotripolyindenyl group, a spirotripolyindenyl group, a spiroisotripolyindenyl group, a furanyl group, a benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, pyrrolyl group, isoindolyl group, carbazolyl group, indenocarbazolyl group, pyridyl group, quinolyl group, isoquinolyl acridinyl group, phenanthridinyl group, benzo-5,6-quinolyl group, benzo-6,7-quinolyl group, benzo-7,8-quinolyl group, pyrazolyl group, indazolyl group, imidazolyl group, benzimidazolyl group, naphthimidazolyl group, phenanth roimidazolyl group, pyridoimidazolyl group, pyrazinoimidazolyl group, quinoxalinoimidazolyl group, oxazolyl group, benzoxazolyl group, naphthoxazolyl group, anthraoxazolyl group, phenanthroxazolyl group, 1 , 2-thiazolyl group, 1,3-thiazolyl group, benzothiazolyl group, pyridazinyl group, benzopyridazinyl group, pyrimidinyl group, benzopyrimidinyl group, quinoxalinyl group, 1,5-diazaanthranyl group, 2,7-diazapyrenyl group, 2 , 3-diazapyrenyl group, 1,6-diazapyrenyl group Nyl group, 1,8-diazapyrenyl group, 4,5-diazapyrenyl group, 4,5,9,10-tetraazaperylenyl group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbolinyl group, phenanthrolinyl group, 1,2,3-triazolyl group, 1,2,4-triazolyl group, benzotriazolyl group, 1,2,3-oxadiazolyl group, 1,2,4-oxadiazolyl 1,2,5-oxadiazolyl group, 1,2,3-thiadiazolyl group, 1,2,4-thiadiazolyl group, 1,2,5-thiadiazolyl group, 1,3,4-thiadiazolyl group, 1,3,5 -triazinyl group, 1,2,4-triazinyl group, 1,2,3-triazinyl group, tetrazolyl group, 1,2,4,5-tetrazinyl group, 1,2,3,4-tetrazinyl group, 1,2,3,5-tetrazinyl group, purinyl group, pteridinyl group, indolidinyl group, benzothiadiazolyl group, 9,9-dimethylacridinyl group, (poly)halogenated benzene, (poly)cyanobenzene, (poly)trifluoromethylbenzene, triaryl selected from one of amino group, adamantane, fluorophenyl group, methylphenyl group, trimethylphenyl group, cyanophenyl group, tetrahydropyrrole, piperidine, methoxy group, silicon group, or from a combination of the two substituents selected.

Two adjacent groups among R ¹ to R ²⁰ are bonded together with the adjacent benzene ring to a C5-C30 5- or 6-membered aryl group ring, or a C5-C30 5- or 6-membered hetero may form one of aryl group rings, and at least one hydrogen in the formed ring is a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C60 monocyclic aryl group, C6-C60 condensed ring aryl group, C6-C60 aryloxy group, C5-C60 monocyclic heteroaryl group, C5-C60 condensed ring heteroaryl group, halogen, C1-C30 chain alkyl group, C3- It may be substituted with any one of a C30 cycloalkyl group, a C1-C10 alkoxy group, a C1-C10 thioalkoxy group, a carbonyl group, a carboxyl group, a nitro group, a cyano group and an amino group.

When the above groups have substituents, the substituents are each independently deuterium, halogen, cyano group, C1-C30 chain alkyl group, C3-C30 cycloalkyl group, C1-C10 alkoxy group, C6 ∼C30 arylamino group, C3-C30 heteroarylamino group, C6-C30 aryl group, C3-C30 heteroaryl group.

Still more preferably, in formula (2-1), R ² , R ⁵ , R ⁸ , R ¹¹ , R ¹⁴ and R ¹⁷ are each independently a hydrogen atom, a substituted or unsubstituted methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, 2-methylbutyl group, cyclohexyl group, fluorine atom, trifluoromethyl group, cyano group, t-butylbenzene, methylphenyl group, phenyl group, triarylamino group, carbazolyl group, pyridyl group, furanyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, adamantane, tetrahydro It is selected from pyrrole, piperidine, silicon group, methoxy group, 9,9-dimethylacridinyl group, imidazole, carbazofuranyl group.

Still more preferably, in formula (2-2), R ² , R ⁵ , R ⁸ and R ¹⁹ are each independently a hydrogen atom, or a substituted or unsubstituted methyl group, ethyl group or n-propyl group , isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, 2-methylbutyl group, cyclohexyl group, fluorine atom, trifluoromethyl group, cyano group, t-butylbenzene, methylphenyl group, phenyl group, triarylamino group, carbazolyl group, pyridyl group, furanyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, adamantane, tetrahydropyrrole, piperidine, silicon group , methoxy, 9,9-dimethylacridinyl, imidazolyl, carbazofuran. R ²¹ is hydrogen, fluorine, a cyano group, or a substituted or unsubstituted pyridyl group, phenyl group, fluorophenyl group, methylphenyl group, trimethylphenyl group, cyanophenyl group, trifluoromethyl group, triarylamino group; , methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, 2-methylbutyl group, cyclohexyl group, hydrogen atom, adamantane, tetrahydropyrrole, piperidine, silicon group, methoxy group, 9,9-dimethylacridinyl group, phenothiazinyl group, phenoxazinyl group, imidazolyl group, carbazofuran, triarylamino group, carbazolyl group, fluorine atom, trifluoromethyl group, cyano group, pyridyl group, furanyl group be done.

Still more preferably, in formula (2-3), R ² , R ⁵ , R ⁸ , R ¹¹ , R ¹⁶ and R ¹⁹ are each independently a hydrogen atom, a substituted or unsubstituted methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, 2-methylbutyl group, cyclohexyl group, fluorine atom, trifluoromethyl group, cyano group, t-butylbenzene, methylphenyl group, phenyl group, triarylamino group, carbazolyl group, pyridyl group, furanyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, adamantane, tetrahydro It is selected from pyrrole, piperidine, silicon group, methoxy group, 9,9-dimethylacridinyl group, imidazolyl group and carbazofuran. R ²¹ is hydrogen, fluorine, a cyano group, or a substituted or unsubstituted pyridyl group, phenyl group, fluorophenyl group, methylphenyl group, trimethylphenyl group, cyanophenyl group, trifluoromethyl group, triarylamino group; , methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, 2-methylbutyl group, cyclohexyl group, hydrogen atom, adamantane, tetrahydropyrrole, piperidine, silicon group, methoxy 9,9-dimethylacridinyl group, imidazolyl group, carbazofuran, triarylamino group, carbazolyl group, fluorine atom, trifluoromethyl group, cyano group, pyridyl group, furanyl group.

In the specification, the expression Ca to Cb indicates that the group has a to b number of carbon atoms, and unless otherwise specified, the number of carbon atoms generally includes the number of carbon atoms in the substituent. do not have.

In the specification, the substituted or unsubstituted C6-C60 aryl group is preferably a C6-C30 aryl group, and includes a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthranyl group, a phenanthryl group, an indenyl group, and a fluorenyl group. and derivatives thereof, a fluoranthenyl group, a triphenylene group, a pyrenyl group, a perylenyl group, a chrysenyl group, and a tetracene group. Specifically, the biphenyl group is selected from 2-biphenyl group, 3-biphenyl group and 4-biphenyl group, and the terphenyl group is p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl- 3-yl and m-terphenyl-2-yl, wherein the naphthyl group includes 1-naphthyl group and 2-naphthyl group, the anthranyl group is selected from 1-anthranyl group, 2-anthranyl group and 9-anthranyl group, and the fluorenyl group is 1 -fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, and 9-fluorenyl group, and said fluorenyl group derivative is selected from 9,9'-dimethylfluorene, 9,9'-spirodifluorene, and benzofluorene. , the pyrenyl group is selected from 1-pyrenyl group, 2-pyrenyl group and 4-pyrenyl group, and the tetracene group is selected from 1-tetracene group, 2-tetracene group and 9-tetracene group.
Heteroatoms in the present invention are generally atoms or atomic groups selected from N, O, S, P, Si and Se, preferably selected from N, O, S.

In the specification, the substituted or unsubstituted C5-C60 heteroaryl group is preferably a C5-C30 heteroaryl group, a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, etc. are more preferred, and specific examples include furanyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl and derivatives thereof. Among them, the carbazolyl group derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole or indolocarbazole.

In the specification, the C1-C30 chain alkyl group is preferably a C1-C10 chain alkyl group, more preferably a C1-C6 chain alkyl group, such as a methyl group and an ethyl group. , n-propyl group, n-butyl group, n-hexyl group, n-octyl group, isopropyl group, isobutyl group, t-butyl group and the like.
In the specification, the C3-C30 cycloalkyl group includes a monocyclic alkyl group and a polycyclic alkyl group, preferably a C3-C10 cycloalkyl group.

Furthermore, the compounds represented by the general formula (1) of the present invention are preferably the following specific structural compounds P-1 to P-405, and these compounds are typical ones.

The present invention provides a The application of any of the compounds indicated is also covered, said application being as a light-emitting layer material in an organic electroluminescent device, preferably as a light-emitting dye and/or sensitizer.

The present invention further provides an organic electroluminescent device comprising a substrate, a first electrode, a second electrode, and one or more organic layers interposed between said first and second electrodes. However, the organic layer is the above general formula (1-1), formula (1-2), formula (1-3), formula (2-1), formula (2-2), and formula (2-3) ).

Specifically, one embodiment of the present invention provides an organic electroluminescent device comprising a substrate, and an anode layer, a plurality of light emitting functional layers and a cathode layer sequentially formed on the substrate. The light emitting functional layer includes a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, the hole injection layer is formed on the anode layer, and the hole transport layer is formed on the hole injection layer. and the cathode layer is formed on the electron transport layer, and the light emitting layer is between the hole transport layer and the electron transport layer. However, the light-emitting layer is the above formula (1-1), formula (1-2), formula (1-3), formula (2-1), formula (2-2), and formula (2-3) any of the compounds of the general formula of the present invention.
OLED devices prepared with the compounds of the present invention have low starting voltage, high luminous efficiency, high color purity, and better service life.

The compound of the present invention has a relatively long service life on the premise that the device has a suitable driving voltage and efficiency, and can be applied not only as a light-emitting material in organic electroluminescent devices, but also in optical sensors, solar cells. , lighting fixtures, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information tags, and other technical fields.

Although the specific reason why the compound of the present invention is excellent in performance when used in an organic electroluminescence device is not clear, it is presumed to be due to the following reasons.

Compared to prior art compounds, in such novel compound structure design of the present invention, it is preferable to introduce donors such as carbazole and its derivatives at the 1, 3 and 5 positions of the central benzene ring, respectively, which are more rigid, Besides making the overall BN resonant scaffold more rigid (advantageous in further reducing its vibrational relaxation and narrowing the spectrum), the preferred carbazole units can also participate in the frontal orbital distribution, reducing the overhang of HOMO and LUMO orbitals. Increase wrap (and improve its radiative transition oscillator strength, ie, luminous efficiency). At the same time, the ortho- and para-positions of nitrogen atoms at positions 1, 3, and 5 all correspond to electron-withdrawing boron atoms. also decreases to different extents, the spectrum is also blue-shifted.

In addition, such a special multi-donor-multi-acceptor structure also favors introducing more intermediate triplets between singlet S1 and triplet T1, and the inverse of singlet and triplet It accelerates the intersystem crossing rate and increases the proportion of the retarded component to reduce the delayed fluorescence lifetime, ultimately reducing the efficiency roll-off and improving the stability of the electroluminescent device. Furthermore, it is more preferable to introduce an R ²¹ group having a certain steric hindrance. It further reduces the half-value width of the material while retaining the properties of the material.

The compounds of the present invention are used both as a light-emitting layer material in organic electroluminescence devices and as a fluorescence sensitizer in organic electroluminescence devices.
In addition, the manufacturing process of the compound of the present invention is simple and easy to implement, the raw materials are readily available, and it is suitable for mass production expansion.

FIG. 1 is a structural schematic diagram of an organic electroluminescent device prepared in the present invention, in which 1 is the substrate, 2 is the anode, 3 is the hole transport layer, and 4 is the organic light-emitting layer. , 5 is the electron transport layer and 6 is the cathode. FIG. 2 is a comparison of the electroluminescence spectra of device D1 prepared in the inventive example and device DD1 prepared in the comparative example. FIG. 3 is a comparison of the electroluminescence spectra of device D1 prepared in the inventive example and device DD1 prepared in the comparative example. FIG. 4 is a comparison of the electroluminescence lifetime of device D1 prepared in the inventive example and device DD1 prepared in the comparative example. FIG. 5 is an electroluminescence spectrum of TTA-type device T1, a device prepared in an example of the present invention.

Specific methods for preparing the above novel compounds of the present invention will be described in detail below by taking several synthesis examples as examples, but the preparation methods of the present invention are not limited to these synthesis examples.

Basic chemicals such as various chemicals used in the present invention, such as petroleum ether, t-butylbenzene, ethyl acetate, sodium sulfate, toluene, dichloromethane, potassium carbonate, boron tribromide, N,N-diisopropylethylamine, reaction intermediates, etc. All raw materials are purchased from Shanghai Taitan Technology Co., Ltd. and Xilong Chemical Co., Ltd. The mass spectrometer used to identify the compounds below is a ZAB-HS type mass spectrometer (manufactured by Micromass, UK).

より具体的に、以下では本発明の代表的な具体的な化合物の合成方法を示す。
（合成実施例）
合成実施例１：
化合物Ｐー１の合成

Methods for synthesizing the compounds of the present invention are briefly described below. First, hydrogen and Cl atoms between X ¹ , X ² and X ³ are ortho-metallated with n-butyllithium, t-butyllithium or the like. Then, boron tribromide or phosphorus trichloride or the like is added to perform metal exchange of lithium-boron or lithium-phosphorus, and then a Bronsted base such as N,N-diisopropylethylamine is added to obtain a tandem boron. Friedel-Crafts Reaction (Tandem Bora-Friedel-Crafts Reaction) can be performed to obtain the desired product.

More specifically, synthesis methods for representative specific compounds of the present invention are shown below.
(Synthesis example)
Synthetic Example 1:
Synthesis of compound P-1

Under a nitrogen atmosphere, a solution of t-butyllithium in pentane (18.96 mL, 1.60 M, 30.34 mmol) was slowly added to a solution of the bromination precursor (13.83 g, 13.79 mmol) in t-butylbenzene (150 mL) at 0°C. , and then heated to 80° C., 100° C., and 120° C., respectively, and reacted for 1 hour. After completion of the reaction, the temperature was lowered to -30°C, boron tribromide (7.6 g, 30.34 mmol) was gradually added, and stirring was continued at room temperature for 0.5 hours. N,N-diisopropylethylamine (5.35 g, 41.37 mmol) was added at room temperature and the reaction was continued at 145° C. for 5 hours before being terminated. The solvent was rotary dried under vacuum, and the target compound P-1 (1.00 g, 8% yield, HPLC analytical purity 99.56%) was obtained by silica gel column (developer: ethyl acetate: petroleum ether = 50:1). A green solid is obtained. MALDI-TOF-MS results: Molecular ion peak: 925.92 Elemental analysis results: theoretical value: C: 85.62%; H: 7.61%; B: 2.30%; N: 4.47%; Values: C: 85.72%; H: 7.66%; B: 2.83%; N: 3.79%.
Synthetic Example 2:
Synthesis of compound P-308

This example is substantially the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-308-1. The desired compound P-308 (1.00 g, 8% yield, HPLC analytical purity 99.56%) is a yellow solid. MALDI-TOF-MS results: molecular ion peak: 926.45 Elemental analysis results: theoretical value: C: 85.62%; H: 7.51%; B: 2.33%; N: 4.545%; Values: C: 85.72%; H: 7.66%; B: 2.83%; N: 3.79%.
Synthetic Example 3:
Synthesis of compound P-300

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-300-1. The desired compound P-300 (0.81 g, 10% yield, HPLC analytical purity 99.66%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 589.76 Elemental analysis results: theoretical value: C: 85.61%; H: 3.59%; B: 3.67%; N: 7.13%; Values: C: 85.12%; H: 4.01 B: 3.58; N: 7.29%.
Synthetic Example 4:
Synthesis of compound P-334

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-334-1. The desired compound P-334 (1.27 g, 10% yield, HPLC analytical purity 99.36%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 919.31 Elemental analysis results: theoretical value: C: 86.20%; H: 3.84%; B: 2.35%; N: 7.62%; Values: C: 85.92%; H: 4.16%; B: 2.53%; N: 7.39%.
Synthetic Example 5:
Synthesis of compound P-301

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-301-1. The desired compound P-301 (1.02 g, 11% yield, HPLC analytical purity 99.55%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 673.89 Elemental analysis results: theoretical value: C: 85.61%; H: 4.94%; B: 3.21%; N: 6.24%; Values: C: 85.12%; H: 4.46%; B: 3.68%; N: 6.74%.
Synthetic Example 6:
Synthesis of compound P-303

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-303-1. The desired compound P-303 (1.42 g, 10% yield, HPLC analytical purity 99.35%) is a yellow solid. MALDI-TOF-MS results: molecular ion peak: 757.89 Elemental analysis results: theoretical values: C, 85.61%; H, 5.99%; B, 2.85%; N, 5.55%; Values: C, 85.41%; H, 5.89%; B, 2.95%; N, 5.75%.
Synthetic Example 7:
Synthesis of compound P-317

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-317-1. The desired compound P-317 (1.44 g, 10% yield, HPLC analytical purity 99.26%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 1045.29 Elemental analysis results: theoretical value: C: 89.58%; H: 4.34%; B: 2.07%; N: 4.02%; Values: C: 89.88%; H: 4.16%; B: 2.18%; N: 3.78%.
Synthetic Example 8:
Synthesis of compound P-330

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-330-1. The desired compound P-330 (1.29 g, 10% yield, HPLC analytical purity 99.36%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 923.31 Elemental analysis results: Theoretical: C, 85.82%; H, 4.26%; B, 2.34%; N, 7.58%; Values: C, 85.83%; H, 4.25%; B, 2.24%; N, 7.68%.
Synthetic Example 9:
Synthesis of compound P-334

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-334-1. The desired compound P-334 (1.27 g, 10% yield, HPLC analytical purity 99.36%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 919.31 Elemental analysis results: theoretical value: C: 86.20%; H: 3.84%; B: 2.35%; N: 7.62%; Values: C: 85.92%; H: 4.16%; B: 2.53%; N: 7.39%.
Synthetic Example 10:
Synthesis of compound P-400

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-400-1. The desired compound P-400 (0.83 g, 10% yield, HPLC analytical purity 99.55%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 603.62 Elemental analysis results: theoretical value: C: 85.61%; H: 3.84%; B: 3.58%; N: 6.97%; Values: C: 85.34%; H: 3.57% B: 3.78%; N: 7.31%.
Synthetic Example 11:
Synthesis of compound P-497

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-497-1. The desired compound P-497 (0.92 g, 10% yield, HPLC analytical purity 99.55%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 665.62 Elemental analysis results: Theoretical: C, 86.65%; H, 3.79%; B, 3.25%; N, 6.32%; Values: C, 86.85%; H, 3.59%; B, 3.05%; N, 6.52%.
Synthetic Example 12:
Synthesis of compound P-498

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-498-1. The desired compound P-498 (0.62 g, 6% yield, HPLC analytical purity 99.75%) is a yellow solid. MALDI-TOF-MS Results: Molecular Ion Peak: 748.11 Elemental Analysis Results: Theoretical: C, 86.63%; H, 4.44%; B, 1.44%; N, 7.48%; Values: C: 86.54%; H: 4.57 B: 1.78; N: 7.11%.
Synthetic Example 13:
Synthesis of compound P-499

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-499-1. The desired compound P-499 (0.62 g, 6% yield, HPLC analytical purity 99.75%) is a yellow solid. MALDI-TOF-MS results: Molecular ion peak: 746.58 Elemental analysis results: theoretical value: C: 86.86%; H: 4.18%; B: 1.45%; N: 7.50%; Values: C: 86.34%; H: 4.57 B: 1.78; N: 7.31%.
Synthetic Example 14:
Synthesis of compound P-4

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 is replaced with an equivalent amount of P-4-1. The desired compound P-4 (0.62 g, 4.5% yield, HPLC analytical purity 99.75%) is a green solid. MALDI-TOF-MS results: Molecular ion peak: 1002.02 Elemental analysis results: theoretical value: C: 86.31%; H: 7.34%; B: 2.16%; N: 4.19%; Values: C: 86.34%; H: 7.27 B: 2.28; N: 4.11%.
Synthetic Example 15:
Synthesis of compound P-7

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-7-1. The desired compound P-7 (0.60 g, 4.4% yield, HPLC analytical purity 99.55%) is a green solid. MALDI-TOF-MS results: molecular ion peak: 1003.01 Elemental analysis results: theoretical values: C, 85.02%; H, 7.24%; B, 2.16%; N, 5.59%; Values: C: 86.31%; H: 7.34%; B: 2.16%; N: 4.19%.
Synthetic Example 16:
Synthesis of compound P-39

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-39-1. The desired compound P-39 (0.60 g, 4.4% yield, HPLC analytical purity 99.55%) is a green solid. MALDI-TOF-MS results: molecular ion peak: 1003.01 Elemental analysis results: theoretical values: C, 85.02%; H, 7.24%; B, 2.16%; N, 5.59%; Values: C: 86.31%; H: 7.34%; B: 2.16%; N: 4.19%.
Synthetic Example 17:
Synthesis of compound P-46

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-46-1. The desired compound P-46 (1.78 g, 12% yield, HPLC analytical purity 99.55%) is a green solid. MALDI-TOF-MS results: molecular ion peak: 1082.85 Elemental analysis results: theoretical values: C, 86.57%; H, 7.55%; B, 2.00%; N, 3.88%; Values: C, 86.36%; H, 7.42%; B, 2.29%; N, 6.69%; O, 3.93%.
Synthetic Example 18:
Synthesis of compound P-64

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-64-1. The desired compound P-64 (1.65 g, 12% yield, HPLC analytical purity 99.35%) is a green solid. MALDI-TOF-MS results: molecular ion peak: 721.48 Elemental analysis results: theoretical values: C, 86.57%; H, 4.61%; B, 3.00%; N, 5.82%; Values: C, 86.64%; H, 4.51%; B, 3.09%; N, 5.76%;
Synthetic Example 19:
Synthesis of compound P-88

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-88-1. The desired compound P-88 (0.78 g, 8% yield, HPLC analytical purity 99.55%) was obtained as a green solid. MALDI-TOF-MS results: Molecular ion peak: 711.24 Elemental analysis results: Theoretical value: C, 72.62%; H, 2.41%; B, 3.04%; F, 16.03%; , 5.91%; experimental values: C, 72.61%; H, 2.43%; B, 3.02%; F, 16.05%;
Synthetic Example 20:
Synthesis of compound P-92

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-92-1. The desired compound P-92 (0.90 g, 8% yield, HPLC analytical purity 99.75%) is a green solid. MALDI-TOF-MS results: Molecular ion peak: 699.28 Elemental analysis results: Theoretical values: C, 86.25%; H, 5.87%; B, 2.68%; N, 5.20%; Values: C, 86.15%; H, 5.87%; B, 2.68%; N, 5.30%.
Synthetic Example 21:
Synthesis of compound P-206

This example is basically the same as Synthesis Example 1, except that in this example P-1-1 was replaced with an equivalent amount of P-206-1. The desired compound P-206 (0.86 g, 6% yield, HPLC analytical purity 99.55%) is a green solid. MALDI-TOF-MS results: Molecular ion peak: 699.28 Elemental analysis results: Theoretical values: C, 70.69%; H, 6.91%; B, 2.09%; N, 4.05%; H, 6.81%; B, 2.19%; N, 4.15%; Si, 16.26%.
Synthetic Example 22:
Synthesis of compound P-95

BBr3 (5.66 mL, 60 mmol) was added to o-dichlorobenzene solution (100 mL) of P-95-1 (10.65 g, 10 mmol) under nitrogen atmosphere, and the reaction was terminated after 24 hours at 245°C. The solvent was rotary dried under vacuum, and the target compound P-95 (0.22 g, 2% yield, HPLC analytical purity 99.56%) was obtained by silica gel column (developer: ethyl acetate: petroleum ether = 50:1). A green solid is obtained. MALDI-TOF-MS results: Molecular ion peak: 1089.65; Elemental analysis results: Theoretical value: C, 85.95%; H, 7.21%; B, 2.98%; N, 3.86%; Experimental values: C, 85.91%; H, 7.25%; B, 2.94; N, 3.90.
Synthetic Example 23:
Synthesis of compound P-114

Under a nitrogen atmosphere, a solution of t-butyllithium in pentane (18.96 mL, 1.60 M, 30.34 mmol) was slowly added to a solution of the bromination precursor (8.84 g, 13.79 mmol) in t-butylbenzene (150 mL) at 0°C. , and then heated to 80° C., 100° C., and 120° C., respectively, and reacted for 1 hour. After completion of the reaction, the temperature was lowered to -30°C, boron tribromide (7.6 g, 30.34 mmol) was gradually added, and stirring was continued at room temperature for 0.5 hour. N,N-diisopropylethylamine (5.35 g, 41.37 mmol) was added at room temperature and the reaction was continued at 145° C. for 5 hours and then cooled to room temperature. A solution of phenylmagnesium chloride in tetrahydrofuran (30 mL, 1.0 M, 30 mmol) was added at room temperature and the reaction was continued for 12 h before being terminated. The solvent was rotary dried under vacuum, and the target compound P-1 (0.49 g, 6% yield, HPLC analytical purity 99.56%) was obtained by silica gel column (developer: ethyl acetate: petroleum ether = 50:1). A green solid is obtained. MALDI-TOF-MS results: molecular ion peak: 588.09 Elemental analysis results: theoretical values: C, 85.78%; H, 3.94%; B, 5.51%; N, 4.76%; Values: C, 85.68%; H, 3.94%; B, 5.61%; N, 4.76%.
Synthetic Example 24:
Synthesis of compound P-110

This example is essentially the same as Synthesis Example 23, except that in this example P-114-1, phenylmagnesium chloride, was replaced with equivalent amounts of P-110-1, t-butylmagnesium chloride, respectively. The desired compound P-110 (0.75 g, 6% yield, HPLC analytical purity 99.45%) is a green solid. MALDI-TOF-MS results: molecular ion peak: 909.70 Elemental analysis results: theoretical values: C, 85.82%; H, 7.53%; B, 3.56%; N, 3.08%; Values: C, 85.84%; H, 7.51%; B, 3.46%; N, 3.18%.

Hereinafter, by specifically applying the compound of the present invention to an organic electroluminescence device, the actual usage performance is measured to demonstrate and verify the technical effects and merits of the present invention.

An organic electroluminescent device includes a first electrode, a second electrode, and a layer of organic material between the two electrodes. The organic material can be divided into multiple regions, for example, the organic material layer can include a hole-transporting region, a light-emitting layer, and an electron-transporting region.

The anode material can be an oxide transparent conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof. Cathode materials include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag ) and any combination thereof can be used.

A hole-transporting region is located between the anode and the light-emitting layer. The hole-transporting region may be a single-layered hole-transporting layer (HTL), including a single-layered hole-transporting layer containing only one compound and a single-layered hole-transporting layer containing multiple compounds. The hole-transporting region may be a multilayer structure including at least one of a hole-injecting layer (HIL), a hole-transporting layer (HTL), and an electron-blocking layer (EBL).

The material of the hole-transporting region is a phthalocyanine derivative such as CuPc, a conductive polymer, or a polymer containing conductive dopants, such as polyphenylene vinylene, polyaniline/dodecylbenzene sulfonic acid (Pani/DBSA), poly(3,4-ethylene dioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly(4-styrenesulfonate) (Pani/PSS), aromatic It may be selected from amine derivatives and the like, but is not limited to these.

The light-emitting layer includes light-emitting dyes (ie, dopants) that emit different wavelength spectra, and also includes a host. The light-emitting layer may be a monochromatic light-emitting layer that emits a single color such as red, green, or blue. Monochromatic light-emitting layers of various colors may be planarly arranged according to pixel patterns, or may overlap to form a color light-emitting layer. When the light-emitting layers of different colors are superimposed, they may be separated from each other or they may be connected. The light-emitting layer may be a single color light-emitting layer that simultaneously emits different colors such as red, green and blue.

The electron-transporting region may be a single-layer electron-transporting layer (ETL), including single-layer electron-transporting layers containing only one compound and single-layer electron-transporting layers containing different compounds. The electron-transporting region may be a multilayer structure including at least one of an electron-injecting layer (EIL), an electron-transporting layer (ETL), and a hole-blocking layer (HBL).

A manufacturing process for an organic electroluminescent device will now be described with reference to FIG. An anode 2, a hole-transporting layer 3, an organic light-emitting layer 4, an electron-transporting layer 5 and a cathode 6 are sequentially deposited on a substrate 1 and sealed. However, when manufacturing the organic light-emitting layer 4, the organic light-emitting layer 4 is formed by a method of co-depositing a wide bandgap material source, an electron donor type material source, an electron acceptor type material source, and a resonance type TADF material source.

Specifically, the manufacturing method of the organic electroluminescent device of the present invention includes the following steps.
1. The glass plate with the applied anode material is sonicated in a commercial detergent, rinsed with deionized water, and sonicated in an acetone:ethanol mixture to remove all moisture in a clean environment. The surface is then baked to maturity, cleaned with UV light and ozone, and bombarded with a low-energy positive ion beam.

2. The glass plate with the anode is placed in a vacuum chamber, evacuated to 1×10 ⁻⁵ to 9×10 ⁻³ Pa, and a hole injection material is vacuum-deposited on the anode layer to form a hole injection layer. The deposition rate is 0.1-0.5 nm/s.
3. A hole-transporting material is vacuum-deposited on the hole-injecting layer to form a hole-transporting layer, and the deposition rate is 0.1-0.5 nm/s.
4. An electron blocking layer is vacuum-deposited on the hole-transporting layer at a deposition rate of 0.1-0.5 nm/s.

5. The organic light-emitting layer of the device is vacuum-deposited on the electron-blocking layer, the organic light-emitting layer material contains the main material and the TADF dye, and the dye reaches a preset doping ratio by the method of multi-source co-evaporation. Secondly, the deposition rate of the main material, the deposition rate of the sensitizer material and the deposition rate of the dye are adjusted.
6. A hole-blocking layer is vacuum-deposited on the organic light-emitting layer at a deposition rate of 0.1-0.5 nm/s.
7. The electron-transporting material of the device is vacuum-deposited on the hole-blocking layer to form an electron-transporting layer, and the deposition rate is 0.1-0.5 nm/s.
8. LiF is vacuum-deposited on the electron transport layer at 0.1-0.5 nm/s as an electron injection layer, and an Al layer is vacuum-deposited at 0.5-1 nm/s as the cathode of the device.

Embodiments of the present invention further provide a display comprising the organic electroluminescent device described above. This display device may specifically be a display device, such as an OLED display, and any product or component having a display function, such as a television, digital camera, mobile phone, tablet, etc., including this display device. This display device and the organic electroluminescence device have the same merits over the conventional technology, and the description thereof is omitted here.
The organic electroluminescence device of the present invention will be further described below with specific examples.
Device Example 1
The structure of the organic electroluminescent device prepared in this example is shown below.

ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3 wt% P-1 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

However, the anode material is ITO. The hole injection layer material is HI, typically with a total thickness of 5-30 nm, 10 nm in this example. The material of the hole transport layer is HT and the total thickness is typically 5-500 nm, 40 nm in this example. Host is the wide-gap main material of the organic light-emitting layer, the compound P-1 of the present invention is a dye, the doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200 nm, and the thickness of the organic light-emitting layer is 30 nm. is. The material of the electron transport layer is ET, and the thickness is generally 5-300 nm, 30 nm in this example. The electron injection layer and cathode materials are chosen to be LiF (0.5 nm) and metallic aluminum (150 nm).

A DC voltage was applied to the organic electroluminescence device D1 prepared in this example, and the characteristics when emitting light of 10 cd/m ² were measured. 0.12, 0.12) and blue light emission with an external quantum efficiency EQE of 28.8% (driving voltage is 3.0 V) was obtained.

Device Example 2
Except for replacing the wide energy gap type main material Host used in the light emitting layer with a TADF type main material TD, the preparation method is the same as in Device Example 1, and the specific device structure is as follows.

ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3 wt% P-1 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The results of measuring the device performance of the organic electroluminescence device D2 prepared in this example were obtained by applying a direct current voltage and measuring the characteristics when emitting 10 cd/m ² , wavelength 469 nm, half width 20 nm, CIE color Blue light emission with coordinates (x, y)=(0.13, 0.12) and an external quantum efficiency EQE of 32.4% (driving voltage is 2.6 V) was obtained.

Device Example 3
The preparation method is the same as that of Device Example 1, except that the dyes used in the emissive layer are replaced with P-1 to P-4. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3 wt% P-4 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

As a result of measuring the device performance of the organic electroluminescence device D3 prepared in this example, a DC voltage was applied and the characteristics when emitting light of 10 cd/m ² were measured. Blue light emission with coordinates (x, y)=(0.13, 0.11) and an external quantum efficiency EQE of 28.3% (driving voltage is 3.0 V) was obtained.

Device Example 4
The preparation method is the same as for Device Example 2, except that dye P-1 in the emissive layer is replaced with P-4. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3 wt% P-4 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The results of measuring the device performance of the organic electroluminescence device D4 prepared in this example were obtained by applying a direct current voltage and measuring the characteristics when emitting 10 cd/m ² , wavelength 462 nm, half width 20 nm, CIE color Blue light emission with coordinates (x, y)=(0.13, 0.11) and an external quantum efficiency EQE of 31.4% (driving voltage is 2.6 V) was obtained.

Device Example 5
The preparation method is the same as in Device Example 1, except that dye P-1 in the emissive layer is replaced with P-7. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3 wt% P-7 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The results of measuring the device performance of the organic electroluminescence device D5 prepared in this example were obtained by applying a direct current voltage and measuring the characteristics when emitting 10 cd/m ² , wavelength 465 nm, half width 22 nm, CIE color Blue light emission with coordinates (x, y)=(0.14, 0.12) and an external quantum efficiency EQE of 29.3% (driving voltage is 3.0 V) was obtained.

Device Example 6
The preparation method is the same as for Device Example 2, except that dye P-1 in the emissive layer is replaced with P-7. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3 wt% P-7 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The results of measuring the device performance of the organic electroluminescence device D6 prepared in this example were obtained by applying a direct current voltage and measuring the characteristics when emitting 10 cd/m ² , wavelength 464 nm, half width 22 nm, CIE color Blue light emission with coordinates (x, y)=(0.12, 0.12) and an external quantum efficiency EQE of 33.6% (driving voltage is 2.6 V) was obtained.

Device Example 7
The preparation method is the same as for Device Example 1, except that dye P-1 in the emissive layer is replaced with P-39. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3 wt% P-39 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The results of measuring the device performance of the organic electroluminescence device D7 prepared in this example were obtained by applying a direct current voltage and measuring the characteristics when emitting 10 cd/m ² , wavelength 469 nm, half width 21 nm, CIE color Blue light emission with coordinates (x, y)=(0.12, 0.13) and an external quantum efficiency EQE of 29.3% (driving voltage is 2.8 V) was obtained.

Device Example 8
The preparation method is the same as for Device Example 2, except that dye P-1 in the emissive layer is replaced with P-39. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3 wt% P-39 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

As a result of measuring the device performance of the organic electroluminescence device D8 prepared in this example, a DC voltage was applied and the characteristics when emitting 10 cd/m ² were measured. Blue light emission with coordinates (x, y)=(0.12, 0.10) and an external quantum efficiency EQE of 32.4% (driving voltage is 2.4 V) was obtained.

Device Example 9
The preparation method is the same as for Device Example 1, except that dye P-1 in the emissive layer is replaced with P-95. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3 wt% P-95 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The results of measuring the device performance of the organic electroluminescence device D9 prepared in this example were obtained by applying a direct current voltage and measuring the characteristics when emitting 10 cd/m ² , wavelength 461 nm, half width 17 nm, CIE color Blue light emission with coordinates (x, y)=(0.11, 0.09) and an external quantum efficiency EQE of 30.3% (driving voltage is 2.8 V) was obtained.

Device Example 10
The preparation method is the same as for Device Example 2, except that the dye P-1 in the emissive layer is replaced with P-95. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3 wt% P-95 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

As a result of measuring the device performance of the organic electroluminescence device D10 prepared in this example, a DC voltage was applied and the characteristics when emitting 10 cd/m ² were measured. Blue light emission with coordinates (x, y)=(0.11, 0.10) and an external quantum efficiency EQE of 32.4% (driving voltage is 2.4 V) was obtained.

Device Example 11
The preparation method is the same as in Device Example 1, except that dye P-1 in the emissive layer is replaced with P-110. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3 wt% P-110 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The results of measuring the device performance of the organic electroluminescence device D11 prepared in this example were obtained by applying a direct current voltage and measuring the characteristics when emitting 10 cd/m ² , wavelength 470 nm, half width 22 nm, CIE color Blue light emission with coordinates (x, y)=(0.12, 0.13) and an external quantum efficiency EQE of 28.3% (driving voltage is 2.8 V) was obtained.

Device Example 12
The preparation method is the same as for Device Example 2, except that dye P-1 in the emissive layer is replaced with P-110. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3 wt% P-110 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The results of measuring the device performance of the organic electroluminescence device D12 prepared in this example were obtained by applying a direct current voltage and measuring the characteristics when emitting 10 cd/m ² , wavelength 471 nm, half width 22 nm, CIE color Blue light emission with coordinates (x, y)=(0.12, 0.14) and an external quantum efficiency EQE of 30.4% (driving voltage is 2.4 V) was obtained.

Device Example 13
The preparation method is the same as in Device Example 1, except that dye P-1 in the emissive layer is replaced with P-114. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3 wt% P-95 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The results of measuring the device performance of the organic electroluminescence device D13 prepared in this example were obtained by applying a direct current voltage and measuring the characteristics when emitting 10 cd/m ² , wavelength 465 nm, half width 19 nm, CIE color Blue light emission with coordinates (x, y)=(0.12, 0.11) and an external quantum efficiency EQE of 29.6% (driving voltage is 2.8 V) was obtained.

Device Example 14
The preparation method is the same as for Device Example 2, except that dye P-1 in the emissive layer is replaced with P-114. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3 wt% P-11 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The results of measuring the device performance of the organic electroluminescence device D14 prepared in this example were obtained by applying a direct current voltage and measuring the characteristics when emitting 10 cd/m ² , wavelength 466 nm, half width 21 nm, CIE color Blue light emission with coordinates (x, y)=(0.12, 0.12) and an external quantum efficiency EQE of 31.4% (driving voltage is 2.4 V) was obtained.

Device Example 15
The preparation method is the same as for Device Example 1, except that dye P-1 in the emissive layer is replaced with P-206. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3 wt% P-206 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The results of measuring the device performance of the organic electroluminescence device D15 prepared in this example were obtained by applying a direct current voltage and measuring the characteristics when emitting 10 cd/m ² , wavelength 462 nm, half width 20 nm, CIE color Blue light emission with coordinates (x, y)=(0.12, 0.10) and an external quantum efficiency EQE of 31.6% (driving voltage is 2.8 V) was obtained.

Device Example 16
The preparation method is the same as for Device Example 2, except that dye P-1 in the emissive layer is replaced with P-206. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3 wt% P-206 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The results of measuring the device performance of the organic electroluminescence device D16 prepared in this example were obtained by applying a direct current voltage and measuring the characteristics when emitting 10 cd/m ² , wavelength 463 nm, half width 22 nm, CIE color Blue light emission with coordinates (x, y)=(0.12, 0.11) and an external quantum efficiency EQE of 34.4% (driving voltage is 2.6 V) was obtained.

Device Example 17
The preparation method is the same as that of Device Example 1, except that the dye in the emissive layer is replaced from P-1 to P-308. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3 wt% P-308 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The device performance was measured for the organic electroluminescence device D17 prepared in this example. Blue emission with a quantum efficiency EQE of 28.8% (driving voltage is 3.0 V) was obtained.

Device Example 18
The preparation method is the same as for Device Example 2, except that the dye in the emissive layer is replaced from P-1 to P-308. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3 wt% P-308 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The results of measuring the device performance of the organic electroluminescence device D17 prepared in this example were obtained by applying a direct current voltage and measuring the characteristics when emitting 10 cd/m ² , wavelength 460 nm, half width 30 nm, CIE color Blue light emission with coordinates (x, y)=(0.13, 0.18) and an external quantum efficiency EQE of 32.4% (driving voltage is 2.6 V) was obtained.

Device Example 19
The preparation method is the same as in Example 1 except that the dye in the emissive layer is replaced with a P-1 to P-300 device. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3 wt% P-300 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

As a result of measuring the device performance of the organic electroluminescence device D19 prepared in this example, a DC voltage was applied and the characteristics when emitting 10 cd/m ² were measured. Blue light emission with coordinates (x, y)=(0.13, 0.16) and an external quantum efficiency EQE of 28.3% (driving voltage is 3.0 V) was obtained.

Device Example 20
The preparation method is the same as that of Device Example 2, except that the dye in the emissive layer is replaced from P-1 to P-300. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3 wt% P-300 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The results of measuring the device performance of the organic electroluminescence device D20 prepared in this example were obtained by applying a DC voltage and measuring the characteristics when emitting 10 cd/m ² , wavelength 452 nm, half width 30 nm, CIE color Blue light emission with coordinates (x, y)=(0.13, 0.15) and an external quantum efficiency EQE of 31.4% (driving voltage: 2.6 V) was obtained.

Device Example 21
The preparation method is the same as that of Device Example 1, except that the dye in the emissive layer is replaced from P-1 to P-334. The device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3 wt% P-334 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The results of measuring the device performance of the organic electroluminescence device D21 prepared in this example were obtained by applying a direct current voltage and measuring the characteristics when emitting 10 cd/m ² , wavelength 465 nm, half width 34 nm, CIE color Blue light emission with coordinates (x, y)=(0.14, 0.19) and an external quantum efficiency EQE of 29.3% (driving voltage is 3.0 V) was obtained.

Device Example 22
The preparation method is the same as that of Device Example 2, except that the dye in the emissive layer is replaced from P-1 to P-334. The device structure is as follows.

ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3 wt% P-334 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The results of measuring the device performance of the organic electroluminescence device D21 prepared in this example were obtained by applying a DC voltage and measuring the characteristics when emitting 10 cd/m ² , wavelength 464 nm, half width 32 nm, CIE color Blue light emission with coordinates (x, y)=(0.12, 0.18) and an external quantum efficiency EQE of 33.6% (driving voltage: 2.6 V) was obtained.

Device Example 23
In this example, a T1 device, which is a triplet-triplet annihilation up-conversion (TTA) type organic electroluminescence device, was manufactured using a TTA-type main AN, and the specific device structure is as follows.
ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/AN: 3 wt% P-1 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

However, the anode material is ITO. The hole injection layer material is HI, typically with a total thickness of 5-30 nm, 10 nm in this example. The material of the hole transport layer is HT and the total thickness is typically 5-500 nm, 40 nm in this example. Host is a TTA-type main material AN, the compound P-1 of the present invention is a dye and the doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200 nm, in this example 30 nm. . The material of the electron transport layer is ET, and the thickness is generally 5-300 nm, 30 nm in this example. The electron injection layer and cathode materials are chosen to be LiF (0.5 nm) and metallic aluminum (150 nm).

A DC voltage was applied to the organic electroluminescence device prepared in this example, and the characteristics when emitting 10 cd/m ² were measured. Blue emission with CIE color coordinates (x, y)=(0.12, 0.10) and an external quantum efficiency EQE of 8.8% was obtained (driving voltage is 2.6 V).

Comparative Device Example 1
Except that the compound P-1 of the present invention used in the light-emitting layer was replaced with the compound P1 of the prior art, the preparation method was the same as in Device Example 1, and the specific device structure is as follows.

ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3 wt% P1 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The results of measuring the device performance of the organic electroluminescence device DD1 prepared in this example were obtained by applying a direct current voltage and measuring the characteristics when emitting light of 10 cd/m ² at a wavelength of 474 nm, a half width of 30 nm, and a CIE color. Blue light emission with coordinates (x, y)=(0.13, 0.20) and an external quantum efficiency EQE of 18.9% (driving voltage is 3.1 V) was obtained.

Comparative Device Example 2
Except that the compound P-1 of the present invention used in the light-emitting layer was replaced with the compound P1 of the prior art, the preparation method was the same as that of Device Example 2, and the specific device structure is as follows.

ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3 wt% P1 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

As a result of measuring the device performance of the organic electroluminescence device DD2 prepared in this example, a DC voltage was applied and the characteristics when emitting 10 cd/m ² were measured. Blue light emission with coordinates (x, y)=(0.13, 0.22) and an external quantum efficiency EQE of 26.9% (driving voltage is 2.8 V) was obtained.

Comparative Device Example 3
Except that the compound P-1 of the present invention used in the light-emitting layer was replaced with the compound P2 of the prior art, the preparation method was the same as in Device Example 1, and the specific device structure is as follows.

ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3 wt% P2 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

As a result of measuring the device performance of the organic electroluminescence device DD3 prepared in this example, a DC voltage was applied and the characteristics when emitting 10 cd/m ² were measured. Blue light emission with coordinates (x, y)=(0.13, 0.11) and an external quantum efficiency EQE of 16.7% (driving voltage is 3.8 V) was obtained.

Comparative Device Example 4
Except that the compound P-1 of the present invention used in the light-emitting layer was replaced with the compound P2 of the prior art, the preparation method was the same as that of Device Example 2, and the specific device structure is as follows.

ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3 wt% P2 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

As a result of measuring the device performance of the organic electroluminescence device DD4 prepared in this example, a DC voltage was applied and the characteristics when emitting 10 cd/m ² were measured. Blue light emission with coordinates (x, y)=(0.14, 0.13) and an external quantum efficiency EQE of 24.9% (driving voltage is 3.0 V) was obtained.

Comparative Device Example 5
Except that the compound P-1 of the present invention used in the light-emitting layer was replaced with the compound P3 of the prior art, the preparation method was the same as in Device Example 1, and the specific device structure is as follows.

ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3 wt% P2 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

The results of measuring the device performance of the organic electroluminescence device DD5 prepared in this example were obtained by applying a direct current voltage and measuring the characteristics when emitting 10 cd/m ² , wavelength 463 nm, half width 29 nm, CIE color Blue light emission with coordinates (x, y)=(0.15, 0.10) and an external quantum efficiency EQE of 22.6% (driving voltage is 3.3 V) was obtained.

Comparative Device Example 6
Except that the compound P-1 of the present invention used in the light-emitting layer was replaced with the compound P3 in the prior art, the preparation method was the same as that of Device Example 2 herein, and the specific device structure is as follows. is.

ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3 wt% P3 (30 nm)/HBL (10 nm) ET (30 nm)/LiF (0.5 nm)/Al (150 nm)

As a result of measuring the device performance of the organic electroluminescence device DD6 prepared in this example, a DC voltage was applied and the characteristics when emitting 10 cd/m ² were measured. Blue light emission with coordinates (x, y)=(0.15, 0.09) and an external quantum efficiency EQE of 27.9% (driving voltage is 3.1 V) was obtained.
The structural formula of each organic material used in each of the above examples is as follows.

上記の各デバイス実施例で調製された有機エレクトロルミネッセンスデバイスＤ１～デバイスＤ１６、デバイスＴ１、及び比較実施例で調製されたデバイスＤＤ１～デバイスＤＤ４の具体的な性能データは詳しく下表１に示される。特に発光スペクトルの半値幅において、実施例は有効な効果を有することが確認され、さらにデバイスの色純度はより優れている。さらにデバイスの外部量子効率も顕著に向上し、効率ロールオフも顕著に改善された。

Specific performance data for the organic electroluminescent devices D1-D16, device T1, and devices DD1-DD4 prepared in each of the above device examples are detailed in Table 1 below. Especially in the half width of the emission spectrum, it is confirmed that the embodiment has an effective effect, and the color purity of the device is better. Furthermore, the external quantum efficiency of the device is significantly improved, and the efficiency roll-off is also significantly improved.

According to the above experimental data, when the preparation of such novel compounds provided by the present invention is applied to organic electroluminescent devices, the devices can achieve good performance of low efficiency roll-off and high luminous efficiency, while at the same time, the electroluminescence Due to the further narrowing of the luminescence spectrum, such novel compounds of the present invention are organic light-emitting functional materials with good performance and are promising for commercial application.

Although the present invention has been described with reference to embodiments, the present invention is not limited to the above embodiments, and various modifications and improvements can be made by those skilled in the art under the spirit of the present invention. It should be understood that the claims summarize the scope of the invention. Obviously, the above examples are merely illustrative examples and are not limitations on the embodiments. For those skilled in the art, other different forms of changes and variations can be made based on the above description.

Claims (8)

General formula (1-1), formula (1-2), or formula (1-3):

(In formulas (1-1), (1-2) and (1-3),
Y ¹ , Y ² and Y ³ are each independently selected from H or B, at most one of which is H;
X ¹ , X ² and X ³ are each independently selected from N or H, at most one of which is H;
m, n and p are each independently selected from 0 or 1;
X ⁴ , X ⁵ and X ⁶ are each independently selected from a single bond or CR, R is a substituted or unsubstituted C1-C30 chain alkyl group, a C3-C30 cycloalkyl group, a C1- C30 haloalkyl group, C1-C30 alkoxy group, C2-C30 alkenyl group, C3-C30 alkynyl group, C6-C60 monocyclic aryl group, C6-C60 condensed ring aryl group, C6-C60 aryloxy a C5-C60 monocyclic heteroaryl group, or a C5-C60 fused ring heteroaryl group;
R ¹ to R ²⁰ are each independently hydrogen, deuterium, or substituted or unsubstituted halogen, C1-C30 chain alkyl group, C3-C30 cycloalkyl group, C1-C10 alkoxy group, C1 to C10 thioalkoxy group, carbonyl group, carboxyl group, nitro group, cyano group, amino group, silicon group, C6-C30 arylamino group, C3-C30 heteroarylamino group, C6-C60 monocyclic aryl group, is selected from one of a C6-C60 condensed ring aryl group, a C6-C60 aryloxy group, a C5-C60 monocyclic heteroaryl group, or a C5-C60 condensed ring heteroaryl group, and R ¹ to R Two adjacent groups of ²⁰ are bonded to each other and together with the adjacent benzene ring, one of C5-C30 5- or 6-membered aryl group ring, C5-C30 5- or 6-membered heteroaryl group ring and at least one hydrogen of the formed ring is a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C60 monocyclic aryl group, a C6-C60 condensed ring aryl group, C6-C60 aryloxy group, C5-C60 monocyclic heteroaryl group, C5-C60 condensed ring heteroaryl group, halogen, C1-C30 chain alkyl group, C3-C30 cycloalkyl group, C1 -C10 alkoxy group, C1-C10 thioalkoxy group, carbonyl group, carboxyl group, nitro group, cyano group, amino group may be substituted by any one,
R ²¹ is hydrogen, deuterium, or substituted or unsubstituted halogen, C1-C30 chain alkyl group, C3-C30 cycloalkyl group, C1-C10 alkoxy group, C1-C10 thioalkoxy group, carbonyl group, carboxyl group, nitro group, cyano group, amino group, C6-C30 arylamino group, C3-C30 heteroarylamino group, C6-C60 monocyclic aryl group, C6-C60 condensed ring aryl group, C6 - selected from one of a C60 aryloxy group, a C5-C60 monocyclic heteroaryl group, or a C5-C60 condensed ring heteroaryl group;
When the group has a substituent, each of the substituents is independently deuterium, halogen, a cyano group, a C1-C30 chain alkyl group, a C3-C30 cycloalkyl group, a C1-C10 alkoxy group, selected from a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C30 aryl group, and a C3-C30 heteroaryl group)
An organic compound characterized by being represented by In formulas (1-1), (1-2), and (1-3),
at least one of m, n and p is 0;
or at least one of m, n and p is 1;
or m is 0, n and p are both 1,
2. The organic compound according to claim 1, wherein m is 1 and both n and p are 0. Formula (2-1), Formula (2-2), or Formula (2-3) below:

(In formulas (2-1), (2-2), and (2-3), R ¹ to R ²¹ each independently have the same limiting range as in claim 1)
The organic compound according to claim 1, represented by: In formula (1-1), formula (1-2), formula (1-3), formula (2-1), formula (2-2), and formula (2-3),
Each of R ¹ to R ²¹ is independently hydrogen, deuterium, or a substituted or unsubstituted methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, 2-methylbutyl group, n-pentyl group, sec-pentyl group, cyclopentyl group, neopentyl group, n-hexyl group, cyclohexyl group, neohexyl group, n-heptyl group, cycloheptyl group, n-octyl group, cyclooctyl group, 2-ethylhexyl group , trifluoromethyl group, pentafluoroethyl group, 2,2,2-trifluoroethyl group, phenyl group, naphthyl group, anthranyl group, benzoanthranyl group, phenanthryl group, benzophenanthryl group, pyrenyl group, chrysenyl group, perylenyl group, fluoranthenyl group, tetracene group, pentacene group, benzopyrenyl group, biphenyl group, azophenyl group, terphenyl group, tripolyphenyl group, p-quaterphenyl group, fluorenyl group, spirobifluorenyl group, dihydrophenane tolyl group, dihydropyrenyl group, tetrahydropyrenyl group, cis- or trans-indenofluorenyl group, tripolyindenyl group, isotripolyindenyl group, spirotripolyindenyl group, spiroisotripolyindenyl group, furanyl group, benzofuranyl group , isobenzofuranyl group, dibenzofuranyl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, pyrrolyl group, isoindolyl group, carbazolyl group, indenocarbazolyl group, pyridyl group, quinolyl group, isoquinolyl group, acridinyl group, phenanthridinyl group, benzo-5,6-quinolyl group, benzo-6,7-quinolyl group, benzo-7,8-quinolyl group, pyrazolyl group, indazolyl group, imidazolyl group, benzimidazolyl group, naphthimidazolyl group, phenyl nanthroimidazolyl group, pyridoimidazolyl group, pyrazinoimidazolyl group, quinoxalinoimidazolyl group, oxazolyl group, benzoxazolyl group, naphthoxazolyl group, anthraoxazolyl group, phenanthroxazolyl group, 1,2-thiazolyl group, 1,3-thiazolyl group, benzothiazolyl group, pyridazinyl group, benzopyridazinyl group, pyrimidinyl group, benzopyrimidinyl group, quinoxalinyl group, 1,5-diazaanthranyl group, 2,7-diazapyrenyl group, 2,3-diazapyrenyl group, 1,6-diazapi renyl group, 1,8-diazapyrenyl group, 4,5-diazapyrenyl group, 4,5,9,10-tetraazaperylenyl group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbolinyl group, phenanthrolinyl group, 1,2,3-triazolyl group, 1,2,4-triazolyl group, benzotriazolyl group, 1,2,3-oxadiazolyl group, 1,2,4-oxadiazolyl 1,2,5_oxadiazolyl group, 1,2,3-thiadiazolyl group, 1,2,4-thiadiazolyl group, 1,2,5-thiadiazolyl group, 1,3,4-thiadiazolyl group, 1,3,5-triazinyl group, 1,2,4-triazinyl group, 1,2,3-triazinyl group, tetrazolyl group, 1,2,4,5-tetrazinyl group, 1,2,3,4-tetrazinyl group, 1,2,3,5-tetrazinyl group, purinyl group, pteridinyl group, indolidinyl group, benzothiadiazolyl group, 9,9-dimethylacridinyl group, halogenated benzene, cyanobenzene, trifluoromethylbenzene, triarylamino group, adamantane, fluorophenyl group, methylphenyl group , a trimethylphenyl group, a cyanophenyl group, a tetrahydropyrrole, a piperidine, a methoxy group, a silicon group, or a combination of the two substituents described above; The substituents are each independently deuterium, halogen, cyano group, C1-C30 chain alkyl group, C3-C30 cycloalkyl group, C1-C10 alkoxy group, C6-C30 arylamino group, C3- 4. The organic compound according to claim 1 or 3, which is selected from one of a C30 heteroarylamino group, a C6-C30 aryl group, and a C3-C30 heteroaryl group. In formula (2-1),
R ² , R ⁵ , R ⁸ , R ¹¹ , R ¹⁴ and R ¹⁷ are each independently a hydrogen atom or a substituted or unsubstituted methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, 2-methylbutyl group, cyclohexyl group, fluorine atom, trifluoromethyl group, cyano group, t-butylbenzene, methylphenyl group, phenyl group, triarylamino group, carbazolyl group, pyridyl group, furanyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, adamantane, tetrahydropyrrole, piperidine, silicon group, methoxy group, 9,9- dimethylacridinyl group, phenothiazinyl group, phenoxazinyl group, imidazole, carbazofuranyl group;
In formula (2-2),
R ² , R ⁵ , R ⁸ and R ¹⁹ are each independently a hydrogen atom, or a substituted or unsubstituted methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group or sec-butyl group, t-butyl group, 2-methylbutyl group, cyclohexyl group, fluorine atom, trifluoromethyl group, cyano group, t-butylbenzene, methylphenyl group, phenyl group, triarylamino group, carbazolyl group, pyridyl group, furanyl group, benzofuranyl group , isobenzofuranyl group, dibenzofuranyl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, adamantane, tetrahydropyrrole, piperidine, silicon group, methoxy group, 9,9-dimethylacridinyl group , phenothiazinyl group, phenoxazinyl group, imidazolyl group, carbazofuran,
R ²¹ is hydrogen, fluorine, a cyano group, or a substituted or unsubstituted pyridyl group, phenyl group, fluorophenyl group, methylphenyl group, trimethylphenyl group, cyanophenyl group, trifluoromethyl group, triarylamino group; , methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, 2-methylbutyl group, cyclohexyl group, hydrogen atom, adamantane, tetrahydropyrrole, piperidine, silicon group, methoxy group, 9,9-dimethylacridinyl group, phenothiazinyl group, phenoxazinyl group, imidazolyl group, carbazofuran, triarylamino group, carbazolyl group, fluorine atom, trifluoromethyl group, cyano group, pyridyl group, furanyl group is,
In formula (2-3),
R ² , R ⁵ , R ⁸ , R ¹¹ , R ¹⁶ and R ¹⁹ are each independently a hydrogen atom, or a substituted or unsubstituted methyl group, ethyl group, n-propyl group, isopropyl group or n-butyl group , isobutyl group, sec-butyl group, t-butyl group, 2-methylbutyl group, cyclohexyl group, fluorine atom, trifluoromethyl group, cyano group, t-butylbenzene, methylphenyl group, phenyl group, triarylamino group, carbazolyl group, pyridyl group , furanyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, thienyl group, benzothienyl group, isobenzothienyl group, dibenzothienyl group, adamantane, tetrahydropyrrole, piperidine, silicon group, methoxy group, 9,9 - dimethylacridinyl group, phenothiazinyl group, phenoxazinyl group, imidazolyl group, carbazofuran;
R ²¹ is hydrogen, fluorine, a cyano group, or a substituted or unsubstituted pyridyl group, phenyl group, fluorophenyl group, methylphenyl group, trimethylphenyl group, cyanophenyl group, trifluoromethyl group, triarylamino group; , methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, 2-methylbutyl group, cyclohexyl group, hydrogen atom, adamantane, tetrahydropyrrole, piperidine, silicon group, methoxy group, 9,9-dimethylacridinyl group, phenothiazinyl group, phenoxazinyl group, imidazolyl group, carbazofuran, triarylamino group, carbazolyl group, fluorine atom, trifluoromethyl group, cyano group, pyridyl group, furanyl group is,
When the group has a substituent, each of the substituents is independently deuterium, halogen, a cyano group, a C1-C30 chain alkyl group, a C3-C30 cycloalkyl group, a C1-C10 alkoxy group, 4. The organic compound according to claim 3, which is selected from one of a C6-C30 arylamino group, a C3-C30 heteroarylamino group, a C6-C30 aryl group, and a C3-C30 heteroaryl group. The following compounds:

4. The organic compound according to claim 1 or 3, selected from of the general formula compound according to any one of claims 1 to 6,
Application as a light-emitting layer material or fluorescent sensitizing material in organic electroluminescence devices. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first and second electrodes,
7. An organic electroluminescent device, wherein the organic layer comprises at least one compound according to any one of claims 1-6.

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