Compound and organic light-emitting device containing the same

Abstract

The present application relates to compounds and organic light-emitting devices containing the same. The compound of one example of the present invention is suitable for organic light-emitting devices and can ensure high efficiency, long life, low driving voltage and driving stability of the organic light-emitting devices.

Description

Technical Field

[0001] The present invention relates to a compound and an organic light-emitting device comprising the same. Background Art

[0002] In an organic light-emitting diode, the materials used as the organic layer can be roughly classified into luminescent materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc. according to their functions. In addition, the above-mentioned luminescent materials can be classified into high molecular weight and low molecular weight according to molecular weight, and can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons according to the luminescence mechanism. The luminescent materials can be classified into blue, green, red luminescent materials and yellow and orange luminescent materials required to reflect better natural colors according to the luminescent color. In addition, in order to increase the color purity and increase the luminous efficiency through energy transfer, the main body / dopant class can be used as a luminescent substance. The principle is that if a dopant with a small energy band gap and excellent luminous efficiency is mixed in a small amount in the auxiliary layer compared with the main body that mainly constitutes the luminescent layer, the excitons generated in the main body are transported to the dopant, thereby emitting light with high efficiency. At this time, the wavelength of the main body moves to the wavelength band of the dopant, so that the desired wavelength of light can be obtained according to the type of dopant and main body used.

[0003] As substances used in such organic light-emitting devices, various compounds are well known. However, in the case of organic light-emitting devices using the well-known substances, the development of new materials continues to be required due to high driving voltage, low efficiency and short life. Therefore, efforts are continuously made to develop organic light-emitting devices with low voltage driving, high brightness and long life using substances with excellent characteristics.

[0004] Prior art literature

[0005] Patent Literature

[0006] (Patent Document 1) Korean Patent Publication No. 10-2015-0086721 Summary of the invention

[0007] The invention provides a compound, a preparation method thereof and an organic light-emitting device comprising the compound.

[0008] However, the problems to be solved by the present invention are not limited to the problems described above, and ordinary technicians in the technical field to which the present invention belongs can clearly understand other problems not described according to the following records.

[0009] The first embodiment of the present invention provides a compound represented by the following Chemical Formula 1:

[0010] Chemical formula 1

[0011]

[0012] In the above chemical formula 1,

[0013] Ar, Ar', Ar1 and Ar2 are each independently substituted or unsubstituted C6-C 30 aryl, or substituted or unsubstituted C3~C 30 The heteroaryl group,

[0014] L1 and L2 are each independently a direct bond, a substituted or unsubstituted C6-C 18 Arylene, or substituted or unsubstituted C3~C 30 Heteroarylene,

[0015] R1 to R4, R and R' are each independently hydrogen, deuterium, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted C2~C 30 Alkenyl, substituted or unsubstituted C6~C 30 aryl, or substituted or unsubstituted C3~C 30 The heteroaryl group, the R and R' may be connected to form a ring or may not form a ring,

[0016] l is 0 or an integer from 1 to 4, and m, n and o are each independently 0 or an integer from 1 to 3.

[0017] A second embodiment of the present invention provides an organic light emitting device including an organic layer containing the compound of the present invention between a first electrode and a second electrode.

[0018] In one embodiment of the compound of the present invention, a fluorene linking group is introduced between the diarylfluorene and the arylamine, thereby maintaining a high LUMO energy level while maintaining a HOMO energy level that is easy to transport holes, and easily blocking electrons. Thus, excitons are effectively formed in the light-emitting layer, thereby realizing a low-voltage and high-efficiency organic light-emitting device.

[0019] In addition, since the π conjugation is increased through the fluorene linker, it has fast hole mobility. The terminal diarylfluorene induces intermolecular π stacking, which makes the molecular film arrangement excellent, improves the fluidity on the film, suppresses the roll-off phenomenon, and realizes a long-life device. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] Figure 1 A schematic diagram showing an organic light emitting device according to an example of the present invention.

[0021] Description of Reference Numerals

[0022] 100: Substrate

[0023] 200: Hole injection layer

[0024] 300: Hole transport layer

[0025] 400: Luminous layer

[0026] 500: Electron transport layer

[0027] 600: Electron injection layer

[0028] 1000: Anode

[0029] 2000: Cathode DETAILED DESCRIPTION

[0030] Hereinafter, examples and embodiments of the present invention will be described in detail with reference to the accompanying drawings so that those skilled in the art can easily implement the present invention.

[0031] However, the present invention can be implemented in many different forms and is not limited to the examples and embodiments described herein. In addition, in the drawings, in order to clearly illustrate the present invention, parts not related to the description are omitted, and similar parts are marked with similar reference numerals throughout the specification.

[0032] Throughout the specification of the present invention, when one component is located “on” another component, it includes not only the case where one component is in contact with the other component, but also the case where other components exist between the two components.

[0033] Throughout the present specification, when a part "includes" a structural element, unless there is a special record to the contrary, it means that other structural elements may also be included, rather than excluding other structural elements. The terms "about", "substantially", etc. used throughout the present specification are used with their numerical values ​​or close to their numerical values ​​when the mentioned meanings indicate inherent preparation and material tolerances, so as to prevent unscrupulous infringers from improperly using the disclosure that mentions accurate or absolute numerical values ​​to help understand the present invention. The terms "(of) step" or "step of" used throughout the present specification do not mean "step for" .

[0034] Throughout the specification of the present invention, the term "combination thereof" contained in the expression of Markush form means a mixture or combination of one or more selected from the group consisting of multiple structural elements recorded in the expression of Markush form, and means including one or more selected from the group consisting of the above-mentioned multiple structural elements.

[0035] Throughout the present specification, the description "A and / or B" means "A or B, or A and B".

[0036] Throughout the present specification, the term "aryl" means a group containing C 5-30 Aromatic hydrocarbon ring groups, for example, phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorenyl, phenanthrenyl, triphenylalkenyl, phenylalkenyl, benzotriphenylene, benzofluorenyl, benzotriphenylene, benzo The term "heteroaryl" refers to an aromatic ring such as a C ring containing at least one hetero element. 3-30 The aromatic ring includes, for example, a pyrrolinyl group, a pyrazinyl group, a pyridyl group, an indolyl group, an isoindolyl group, a furyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a benzophenylthio group, a dibenzophenylthio group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a thienyl group, and an aromatic heterocyclic group formed from a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, an indole ring, a quinoline ring, an acridinium ring, a pyrrolidine ring, a dioxane ring, a piperidine ring, a morpholine ring, a piperazine ring, a carbazole ring, a furan ring, a thiophene ring, an oxazole ring, an oxadiazole ring, a benzoxazole ring, a thiazole ring, a thiadiazide ring, a benzothiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, and a dibenzofuran ring.

[0037] In the present invention, the term "substituted or unsubstituted" refers to a group selected from deuterium, halogen, amino, nitrile, nitro, or C1-C 20 Alkyl, C2~C 20 Alkenyl, C1~C 20 Alkoxy, C3~C 20 Cycloalkyl, C3~C 20 Heterocycloalkyl, C6~C 30 The aromatic group and C3~C 30 In addition, throughout the specification of the present invention, the same reference numerals have the same meaning unless otherwise specified.

[0038] Throughout the present specification, the term "fluorene" may include fluorenes in which the hydrogen bonded to the ninth carbon is replaced by a substituted or unsubstituted C 1-20 Alkyl, substituted or unsubstituted C 5-30 aryl, or substituted or unsubstituted C 3-30 The case of heteroaryl substitution.

[0039] The first embodiment of the present invention provides a compound represented by the following Chemical Formula 1:

[0040] Chemical formula 1

[0041]

[0042] In the above chemical formula 1,

[0043] Ar, Ar', Ar1 and Ar2 are each independently substituted or unsubstituted C6-C 30 aryl, or substituted or unsubstituted C3~C 30 The heteroaryl group,

[0044] L1 and L2 are each independently a direct bond, a substituted or unsubstituted C6-C 18 Arylene, or substituted or unsubstituted C3~C 30 Heteroarylene,

[0045] R1 to R4, R and R' are each independently hydrogen, deuterium, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C1~C 30 Alkoxy, substituted or unsubstituted C2~C 30 Alkenyl, substituted or unsubstituted C6~C 30 aryl, or substituted or unsubstituted C3~C 30 The heteroaryl group, the R and R' may be connected to form a ring or may not form a ring,

[0046] l is 0 or an integer from 1 to 4, and m, n and o are each independently 0 or an integer from 1 to 3.

[0047] In the compound of the above chemical formula 1, the fluorene linker is located between the diarylfluorene and the arylamine, maintaining a HOMO energy level that is easy to transport holes, while maintaining a high LUMO energy level that is easy to block electrons. Thus, excitons are effectively formed in the light-emitting layer, and a low-voltage and high-efficiency organic light-emitting device can be realized.

[0048] In addition, since the π conjugation is increased through the fluorene linker, it has fast hole mobility. The terminal diarylfluorene induces intermolecular π stacking, which makes the molecular film arrangement excellent, improves the fluidity on the film, suppresses the roll-off phenomenon, and realizes a long-life device.

[0049] Furthermore, in one embodiment of the present invention, in the chemical formula 1, Ar1 and Ar2 can be independently selected from the group consisting of phenyl, biphenyl, triphenyl, naphthyl, fluorene, dibenzofuran, dibenzothiophene, and combinations thereof.

[0050] Furthermore, in one embodiment of the present invention, the compound can be represented by the following Chemical Formula 2.

[0051] Chemical formula 2

[0052]

[0053] In the above chemical formula 2,

[0054] Ar1, Ar2, R1 to R4, R, R', L1, L2, l, m, n and o are as defined in the above chemical formula 1,

[0055] R5 to R6 are each independently hydrogen, deuterium, substituted or unsubstituted C1-C 24 Alkyl, substituted or unsubstituted C1~C 24 Alkoxy, substituted or unsubstituted C2~C 24 Alkenyl, substituted or unsubstituted C6~C 24 aryl, or substituted or unsubstituted C3~C 24 The heteroaryl group,

[0056] p and q are each independently 0 or an integer from 1 to 5.

[0057] The compound represented by the above Chemical Formula 2 has diphenylfluorene at the terminal, thereby minimizing the bulkiness of the molecule and improving intermolecular stacking, thereby having rapid hole mobility.

[0058] In one embodiment of the present invention, the compound can be represented by the following Chemical Formula 3 or Chemical Formula 4.

[0059] Chemical formula 3

[0060]

[0061] Chemical formula 4

[0062]

[0063] In the above Chemical Formula 3 and Chemical Formula 4,

[0064] Ar1, Ar2, R1 to R6, R, R', L1, L2, l, m, n, o, p and q are as defined in the above Chemical Formula 2.

[0065] Compared with the case where the compound represented by the above Chemical Formula 3 or Chemical Formula 4 has both linking groups L1 and L2, the molecular weight is relatively low and the evaporation temperature may be lowered, thereby providing thermal stability when manufacturing an organic light-emitting device.

[0066] In one embodiment of the present invention, in the above Chemical Formulae 1 to 4, L1 and L2 may each independently be a direct bond or a phenylene group.

[0067] In one embodiment of the present invention, the compound can be represented by the following Chemical Formula 5.

[0068] Chemical formula 5

[0069]

[0070] In the above chemical formula 5,

[0071] Ar1, Ar2, R1 to R6, R, R', l, m, n, o, p and q are as defined in the above Chemical Formula 2.

[0072] In the compound represented by the above Chemical Formula 5, fluorene is directly bonded to the arylamine and the diarylfluorene, and a high LUMO can be maintained, thereby making it easier to block electrons.

[0073] In one embodiment of the present invention, the compound can be represented by one of the following Chemical Formulas 6 to 8.

[0074] Chemical formula 6

[0075]

[0076] Chemical formula 7

[0077]

[0078] Chemical formula 8

[0079]

[0080] In the above Chemical Formulae 6 to 8,

[0081] Ar1, Ar2, R1 to R6, R, R′, L1 and L2 are as defined in the above Chemical Formula 2.

[0082] In one embodiment of the present invention, in the above Chemical Formula 7 and Chemical Formula 8, L1 and L2 may be directly bonded or phenylene groups, respectively. In this case, the exciton blocking effect can be maximized by maintaining a high T1, thereby manufacturing a high-efficiency organic light-emitting device.

[0083] The compounds represented by the above Chemical Formulae 6 to 8 combine arylamine at the second position of fluorene as an intermediate linker to form HOMO suitable for the hole transport layer, thereby reducing the driving voltage.

[0084] In one embodiment of the present invention, the compound can be represented by the following Chemical Formula 9.

[0085] Chemical formula 9

[0086]

[0087] In the above chemical formula 9,

[0088] Ar1, Ar2, R1 to R6, R and R' are as defined in the above Chemical Formula 2.

[0089] In the compound represented by the chemical formula 9, the arylamine and diarylfluorene are bonded to the second and seventh positions of fluorene as an intermediate linker, and the overall linearity is maintained, so that the molecular arrangement becomes excellent, thereby having fast hole mobility.

[0090] In one embodiment of the present invention, the compound can be represented by the following Chemical Formula 10 or Chemical Formula 11.

[0091] Chemical formula 10

[0092]

[0093] Chemical formula 11

[0094]

[0095] In the above Chemical Formula 10 or Chemical Formula 11,

[0096] Ar1, Ar2, R1 to R6 are as defined in the above chemical formula 2,

[0097] R7 and R8 are each independently substituted or unsubstituted C1-C 30 The alkyl group

[0098] Ar3 and Ar4 are each independently substituted or unsubstituted C6-C 30 aryl, or substituted or unsubstituted C3~C 30 The heteroaryl group.

[0099] In one embodiment of the present invention, Ar3 and Ar4 may be independently selected from the group consisting of phenyl, biphenyl, triphenyl, naphthyl, fluorene and combinations thereof.

[0100] The compound represented by the above Chemical Formula 10 or Chemical Formula 11 has a dialkylfluorene or a diarylfluorene as an intermediate linking group, thereby inducing excellent intermolecular stacking.

[0101] In one example of the present invention, in the above Chemical Formulae 2 to 11, Ar1 and Ar2 may be each independently selected from the group consisting of a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, a fluorene group, a dibenzofuran group, a dibenzothiophene group, and a combination thereof.

[0102] According to an example of the present invention, the compound represented by the above chemical formulas 1 to 11 may be one of the following compounds, but may not be limited thereto:

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148] In one embodiment of the present invention, the compound represented by the above chemical formula 1, more specifically, may be compound numbers 1 to 19, 21 to 26, 101 to 104, 130 to 141, 159 to 162, 191 to 194, 201, 206 to 208, 351 to 369, 371 to 376, 451 to 454, 480 to 491, 509 to 512, 541 to 544, 55 1, 556-558, 701-719, 721-726, 801-804, 830-841, 859-862, 891-894, 901, 906-908, 1051-1069, 1071-1076, 1151-1154, 1180-1191, 1209-1212, 1241-1244, 1251, 1256-1258. These compounds reduce excessive conjugation and minimize the molecular weight, thereby maintaining an appropriate HOMO while having a higher LUMO and T1, and can suppress the thermal decomposition of the compound during the vapor deposition process.

[0149] According to an example of the present invention, the compound represented by the above Chemical Formula 1 can be synthesized by the following reaction formula, but may not be limited thereto.

[0150]

[0151] In the above reaction formula, h is a halogen, and other symbols are the same as those in the above chemical formula 1.

[0152] The second embodiment of the present invention provides an organic light-emitting device including a compound represented by any one of the above Chemical Formulae 1 to 11. The organic light-emitting device may include one or more organic layers including the compound of the present invention between the first electrode and the second electrode.

[0153] In one embodiment of the present invention, the organic layer may be a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, but may not be limited thereto. In addition, the compound of the present invention may be used alone or together with a known organic light-emitting compound when forming an organic layer.

[0154] In one example of the present invention, the organic light emitting device may include an organic layer containing a hole transporting substance and an organic layer containing a compound represented by the chemical formula 1, but may not be limited thereto. According to one example of the present invention, as described above, the compound of the chemical formula 1 may be represented by any one of chemical formulas 2 to 11.

[0155] The above-mentioned organic light-emitting device may include one or more organic layers such as a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL) between the anode and the cathode.

[0156] For example, the organic light emitting device may be Figure 1 The organic light-emitting device can be stacked in order from bottom to top: anode (hole injection electrode 1000) / hole injection layer 200 / hole transport layer 300 / luminescent layer 400 / electron transport layer 500 / electron injection layer 600 / cathode (electron injection electrode 2000).

[0157] exist Figure 1 In the embodiment, the substrate 100 may be a substrate for an organic light-emitting device, and in particular, may be a transparent glass substrate or a flexible plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness.

[0158] The hole injection electrode 1000 is used as an anode for injecting holes into the organic light emitting device. In order to inject holes, a material with a low work function is used, and it can be formed of a transparent material such as indium tin oxide (ITO), indium zinc oxide (IZO), and graphene.

[0159] The hole injection layer material is deposited on the anode electrode by vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett) method, etc., thereby forming the hole injection layer 200. When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer 200, the structure and thermal characteristics of the desired hole injection layer, etc., but generally, the deposition temperature is 50-500°C, 10 -8 Up to 10 -3 torr (torr) vacuum degree, 0.01 to The deposition rate, The layer thickness is appropriately selected within the range of 10 to 5 μm.

[0160] Next, a hole transport layer material is deposited on the hole injection layer 200 by vacuum deposition, spin coating, casting, LB method, etc., thereby forming the hole transport layer 300. When the hole transport layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used, but generally, it is preferred to select conditions within the same range as those for forming the hole injection layer.

[0161] The hole transport layer 300 may use the compound of the present invention. As described above, the compound of the present invention may be used alone or together with a known compound. In addition, according to one embodiment of the present invention, the hole transport layer 300 may be more than one layer and may include a hole transport layer formed only of a known substance. In addition, according to one embodiment of the present invention, a light-emitting auxiliary layer may be formed on the hole transport layer 300.

[0162] The light-emitting layer material is deposited on the hole transport layer 300 or the light-emitting auxiliary layer by vacuum deposition, spin coating, casting, LB method, etc., thereby forming the light-emitting layer 400. In the case of forming the light-emitting layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but generally, it is preferred to select conditions within the same range as those for forming the hole injection layer. In addition, the light-emitting layer material can use a known compound as a host or a dopant.

[0163] Furthermore, in the light-emitting layer, when used together with a phosphorescent dopant, in order to prevent triplet excitons or holes from diffusing to the electron transport layer, a hole suppression material (HBL) may be stacked by vacuum deposition or spin coating. The hole suppression material that can be used at this time is not particularly limited, but any substance can be selected from the known substances used as hole suppression materials. For example, oxadiazole derivatives or triazole derivatives, phenanthroline derivatives or hole suppression materials described in Japanese Patent Laid-Open No. 11-329734 (A1) may be cited. Typically, Balq (bis (8-hydroxy-2-methylquinoline) -aluminum biphenyl phenolate), phenanthroline (phenanthroline) compounds (such as BCP (BassoCoupoline) of Universal Display (UDC) Company) and the like may be used.

[0164] The electron transport layer 500 is formed on the light emitting layer 400 formed as above. At this time, the electron transport layer can be formed by vacuum deposition, spin coating, casting, etc. Moreover, the deposition conditions of the electron transport layer vary depending on the compound used, but generally, it is preferred to select conditions within the same range as those for forming the hole injection layer.

[0165] Afterwards, an electron injection layer material may be deposited on the electron transport layer 500 to form the electron injection layer 600. At this time, the electron transport layer may be formed of conventional electron injection layer materials by vacuum deposition, spin coating, casting, etc.

[0166] The hole injection layer 200, the hole transport layer 300, the light emitting layer 400, and the electron transport layer 500 of the organic light emitting device may use the compound of the present invention or the following substances, or the compound of the present invention and known substances may be used together.

[0167]

[0168] The cathode 2000 for injecting electrons is formed on the electron injection layer 600 by vacuum deposition or sputtering. Various metals can be used as the cathode, and specific examples include aluminum, gold, silver, and the like.

[0169] The organic light-emitting device of the present invention can not only adopt an organic light-emitting device with an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode structure, but can also adopt the structure of an organic light-emitting device with multiple structures. According to needs, one or two intermediate layers can be formed.

[0170] As described above, the thickness of each organic layer formed according to the present invention can be adjusted to a desired extent, preferably, specifically, 1 to 1000 nm, more specifically, 5 to 200 nm.

[0171] In addition, in the present invention, the organic layer including the compound represented by the above Chemical Formula 1 can adjust the thickness of the organic layer in molecular units, and thus has advantages of uniform surface and excellent morphological stability.

[0172] The organic light-emitting compound of this embodiment can be applied to the contents described in the first embodiment of the present invention, but may not be limited thereto.

[0173] Hereinafter, the present invention will be described in more detail by way of examples, but the scope of the present invention is not limited to these examples.

[0174] Example

[0175] Synthesis of intermediates

[0176] In order to synthesize the target compound, intermediate IM was synthesized as follows.

[0177]

[0178] Preparation Example 1: Synthesis of Intermediate (IM1)

[0179]

[0180] In a round-bottom flask, 5.1 g of (9,9-diphenyl-9H-fluoren-2-yl)boronic acid and 10.0 g of 2,7-dibromo-9,9-dimethyl-9H-fluorene were dissolved in 200 ml of 1,4-dioxan, 40 ml of K2CO3 (2M) and 1.0 g of Pd(PP h3)4 were added, and the mixture was stirred under reflux. The reaction was confirmed by thin layer chromatography (TLC), and water was added to terminate the reaction. The organic layer was extracted with methylcellulose (MC), filtered under reduced pressure, and then purified by column to obtain 11.9 g (yield 71%) of IM1.

[0181] The following IM2 to IM8 were synthesized using the same method as IM1 above, specifically, using different starting materials as shown in Table 1 below.

[0182]

[0183] Table 1

[0184]

[0185] Compound synthesis

[0186] Using the above intermediates IM1 to IM8, target compounds 1 to 20 were synthesized.

[0187] Synthesis of compound 1

[0188]

[0189] In a round-bottom flask, 3.0 g of IM1, 1.25 g of N-phenyl-[1,1'-biphenyl]-4-amine, 0.7 g of t-BuONa, 0.2 g of Pd2(dba)3, and 0.2 ml of (t-Bu)3P were dissolved in 80 ml of toluene and refluxed with stirring. The reaction was confirmed by thin layer chromatography (TLC), and the reaction was terminated after adding water. The organic layer was extracted with methylcellulose (MC), filtered under reduced pressure, and then column purified and recrystallized to obtain 2.69 g (yield 70%) of compound 1. m / z: 753.34 (100.0%), 754.34 (63.1%), 755.35 (19.6%), 756.35 (4.0%)

[0190] Synthesis of compound 2

[0191]

[0192] Compound 2 was synthesized by the same method as compound 1 using 4-(naphthalen-1-yl)-N-phenylaniline instead of N-phenyl-[1,1'-biphenyl]-4-amine. (Yield 65%) m / z: 803.36 (100.0%), 804.36 (67.6%), 805.36 (22.7%), 806.37 (4.9%)

[0193] Synthesis of compound 3

[0194]

[0195] Compound 3 was synthesized by the same method as compound 1 using di([1,1'-biphenyl]-4-yl)amine instead of N-phenyl-[1,1'-biphenyl]-4-amine. (Yield 70%) m / z: 829.37 (100.0%), 830.37 (69.6%), 831.38 (24.0%), 832.38 (5.4%) Synthesis of compound 4

[0196]

[0197] Compound 4 was synthesized by the same method as compound 1 using 4-(dibenzo[b,d]furan-4-yl)-N-phenylanilin instead of N-phenyl-[1,1'-biphenyl]-4-amine. (Yield 60%) m / z: 843.35 (100.0%), 844.35 (69.6%), 845.36 (24.0%), 846.36 (5.5%)

[0198] Synthesis of compound 5

[0199]

[0200] Compound 5 was synthesized by the same method as compound 1 using 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine instead of N-phenyl-[1,1'-biphenyl]-4-amine. (Yield 63%) m / z: 793.37 (100.0%), 794.37 (66.3%), 795.38 (21.8%), 796.38 (4.7%)

[0201] Synthesis of compound 6

[0202]

[0203] Compound 6 was synthesized by the same method as compound 1 using IM3 instead of IM1. (Yield 67%) m / z: 753.34 (100.0%), 754.34 (63.1%), 755.35 (19.6%), 756.35 (4.0%)

[0204] Synthesis of compound 7

[0205]

[0206] Compound 7 was synthesized by the same method as compound 1 using IM3 and 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine instead of IM1 and N-phenyl-[1,1'-biphenyl]-4-amine. (Yield 63%) m / z: 793.37 (100.0%), 794.37 (66.3%), 795.38 (21.8%), 796.38 (4.7%)

[0207] Synthesis of compound 8

[0208]

[0209] Compound 8 was synthesized by the same method as compound 1 using IM5 and 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine instead of IM1 and N-phenyl-[1,1'-biphenyl]-4-amine. (Yield 70%) m / z: 793.37 (100.0%), 794.37 (66.3%), 795.38 (21.8%), 796.38 (4.7%)

[0210] Synthesis of compound 9

[0211]

[0212] Compound 9 was synthesized by the same method as compound 1 using IM5 and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine instead of IM1 and N-phenyl-[1,1'-biphenyl]-4-amine. (Yield 71%) m / z: 869.40 (100.0%), 870.41 (73.1%), 871.41 (26.3%), 872.41 (6.2%), 873.42 (1.1%)

[0213] Synthesis of compound 10

[0214]

[0215] Compound 10 was synthesized by the same method as compound 1 using IM7 and 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine instead of IM1 and N-phenyl-[1,1'-biphenyl]-4-amine. (Yield 60%) m / z: 793.37 (100.0%), 794.37 (66.3%), 795.38 (21.8%), 796.38 (4.7%)

[0216] Synthesis of compound 11

[0217]

[0218] Compound 11 was synthesized by the same method as compound 1 using IM2 and diphenylamine instead of IM1 and N-phenyl-[1,1'-biphenyl]-4-amine. (Yield 63%) m / z: 801.34 (100.0%), 802.34 (67.4%), 803.35 (22.5%), 804.35 (4.9%)

[0219] Synthesis of compound 12

[0220]

[0221] Compound 12 was synthesized by the same method as compound 1 using IM2 instead of IM1. (Yield 65%) m / z: 877.37 (100.0%), 878.37 (73.9%), 879.38 (27.0%), 880.38 (6.5%), 881.38 (1.1%)

[0222] Synthesis of compound 13

[0223]

[0224] Compound 13 was synthesized by the same method as compound 1 using IM3 and N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine instead of IM1 and N-phenyl-[1,1'-biphenyl]-4-amine. (Yield 65%) m / z: 829.37 (100.0%), 830.37 (69.6%), 831.38 (24.0%), 832.38 (5.4%)

[0225] Synthesis of compound 14

[0226]

[0227] Compound 14 was synthesized by the same method as compound 1 using IM4 and diphenylamine instead of IM1 and N-phenyl-[1,1'-biphenyl]-4-amine. (Yield 67%) m / z: 801.34 (100.0%), 802.34 (67.4%), 803.35 (22.5%), 804.35 (4.9%)

[0228] Synthesis of compound 15

[0229]

[0230] Compound 15 was synthesized by the same method as compound 1 using IM4 instead of IM1. (Yield 73%) m / z: 877.37 (100.0%), 878.37 (73.9%), 879.38 (27.0%), 880.38 (6.5%), 881.38 (1.1%)

[0231] Synthesis of compound 16

[0232]

[0233] Compound 16 was synthesized by the same method as compound 1 using IM5 instead of IM1. (Yield 66%) m / z: 753.34 (100.0%), 754.34 (63.1%), 755.35 (19.6%), 756.35 (4.0%)

[0234] Synthesis of compound 17

[0235]

[0236] Compound 17 was synthesized by the same method as compound 1 using IM6 and diphenylamine instead of IM1 and N-phenyl-[1,1'-biphenyl]-4-amine. (Yield 65%) m / z: 801.34 (100.0%), 802.34 (67.4%), 803.35 (22.5%), 804.35 (4.9%)

[0237] Synthesis of compound 18

[0238]

[0239] Compound 18 was synthesized by the same method as compound 1 using IM6 instead of IM1. (Yield 68%) m / z: 877.37 (100.0%), 878.37 (73.9%), 879.38 (27.0%), 880.38 (6.5%), 881.38 (1.1%)

[0240] Synthesis of compound 19

[0241]

[0242] Compound 19 was synthesized by the same method as compound 1 using IM7 and N-phenyl-[1,1'-biphenyl]-2-amine instead of IM1 and N-phenyl-[1,1'-biphenyl]-4-amine. (Yield 62%) m / z: 753.34 (100.0%), 754.34 (63.1%), 755.35 (19.6%), 756.35 (4.0%)

[0243] Synthesis of compound 20

[0244]

[0245] Compound 20 was synthesized by the same method as compound 1 using IM8 and diphenylamine instead of IM1 and N-phenyl-[1,1'-biphenyl]-4-amine. (Yield 60%) m / z: 801.34 (100.0%), 802.34 (67.4%), 803.35 (22.5%), 804.35 (4.9%)

[0246] Preparation of organic light-emitting devices

[0247] Example 1 (hole transport layer)

[0248] Ultrasonication of distilled water After the distilled water washing is completed, the glass substrate coated with indium tin oxide (ITO) is ultrasonically cleaned using a solvent such as isopropyl alcohol, acetone, methanol, etc., and after drying, it is transferred to a plasma cleaning machine, and then the substrate is cleaned using oxygen plasma for 5 minutes. Then, a thermal evaporator is used on the top of the indium tin oxide substrate as a hole injection layer. (H101) was used to make the film. HATCN was used to form a film as a hole transport layer. After the film is formed by compound 1, 3% BH01:BD01 is doped as the above-mentioned light-emitting layer to Next, as an electron transport layer, After the film was made by mixing ET01 and Liq (1:1), LiF A film was formed by using aluminum (Al) and the device was encapsulated in a glove box to prepare an organic light-emitting device.

[0249] Example 2 to Example 10

[0250] By the same method as in Example 1, an organic light-emitting device in which a film was formed using Compounds 2 to 10 instead of Compound 1 was manufactured.

[0251] Comparative Examples 1-1 to 1-8

[0252] By the same method as in Example 1, an organic light-emitting device in which a film was formed using Ref. 1 to Ref. 8 instead of Compound 1 was manufactured.

[0253]

[0254] Example 11 (luminescent auxiliary layer)

[0255] Ultrasonication of distilled water After the distilled water washing is completed, the glass substrate coated with indium tin oxide (ITO) is ultrasonically cleaned using a solvent such as isopropyl alcohol, acetone, methanol, etc., and after drying, it is transferred to a plasma cleaning machine, and then the substrate is cleaned using oxygen plasma for 5 minutes. Then, a thermal evaporator is used on the top of the indium tin oxide substrate as a hole injection layer. (H101) was used to make the film. HATCN was used to form a film as a hole transport layer. BPA is used to make a film as a light-emitting auxiliary layer. After the film is formed by compound 11, 7% of the host PH01: PH02 (5:5) and the dopant Ir (ppy) 3 are doped as the above-mentioned light-emitting layer. Next, as an electron transport layer, After the film was made by mixing ET01 and Liq (1:1), LiF, 1 A film was formed by using aluminum (Al) and the device was sealed (Encapsulation) in a glove box to prepare an organic light-emitting device.

[0256] Example 12 to Example 20

[0257] By the same method as in Example 11, an organic light-emitting device in which a film was formed using Compounds 12 to 20 instead of Compound 11 was manufactured.

[0258] Comparative Examples 2-1 to 2-8

[0259] By the same method as in Example 11, an organic light-emitting device in which a film was formed using the above-mentioned Ref. 1 to Ref. 8 instead of Compound 11 was manufactured.

[0260] Performance evaluation of organic light-emitting devices

[0261] A voltage was applied using a Keithley 2400 source measure unit to inject electrons and holes, and the brightness of the light was measured using a Konica Minolta spectroradiometer (CS-2000). The current density and brightness for the applied voltage were measured under atmospheric pressure conditions to evaluate the performance of the organic light-emitting devices of the embodiments and comparative examples. The results are shown in Table 2 (hole transport layer embodiment) and Table 3 (luminescence auxiliary layer embodiment).

[0262] Table 2

[0263] Op.V <![CDATA[mA / cm 2 ]]> Cd / A QE(%) CIEx CIE LT95 Example 1 3.86 10 7.20 6.14 0.140 0.109 125 Example 2 3.85 10 7.23 6.10 0.140 0.110 120 Example 3 3.84 10 7.30 6.13 0.141 0.110 130 Example 4 3.85 10 7.20 6.12 0.140 0.110 110 Example 5 3.84 10 7.25 6.10 0.141 0.110 116 Example 6 3.81 10 7.30 6.25 0.140 0.110 120 Example 7 3.83 10 7.33 6.27 0.140 0.110 123 Example 8 3.80 10 7.22 6.20 0.140 0.111 140 Example 9 3.84 10 7.20 6.20 0.139 0.111 133 Example 10 3.82 10 7.25 6.24 0.141 0.110 120 Comparative Example 1-1 4.22 10 6.05 4.90 0.14 0.114 20 Comparative Example 1-2 4.07 10 6.77 5.56 0.143 0.111 40 Comparative Examples 1-3 4.08 10 6.80 5.70 0.141 0.110 45 Comparative Examples 1-4 4.10 10 6.39 5.25 0.141 0.112 33 Comparative Examples 1-5 4.10 10 7.00 6.03 0.141 0.111 70 Comparative Examples 1-6 4.07 10 6.95 5.84 0.142 0.112 80 Comparative Examples 1-7 4.00 10 7.05 6.03 0.141 0.110 95 Comparative Examples 1-8 4.15 10 7.06 5.98 0.140 0.111 87

[0264] Table 3

[0265] Op.V <![CDATA[mA / cm 2 ]]> Cd / A QE(%) CIEx CIE LT95 Embodiment 11 4.71 10 57.60 16.50 0.301 0.620 180 Example 12 4.70 105 57.66 16.50 0.299 0.619 191 Example 13 4.73 10 57.64 16.51 0.298 0.619 170 Embodiment 14 4.76 10 57.65 16.55 0.300 0.620 202 Embodiment 15 4.77 10 57.70 16.57 0.298 0.619 197 Example 16 4.81 10 57.71 16.60 0.298 0.619 182 Embodiment 17 4.80 10 57.65 16.58 0.297 0.618 190 Embodiment 18 4.80 10 57.63 16.50 0.302 0.620 210 Embodiment 19 4.81 10 57.60 16.55 0.300 0.620 175 Embodiment 20 4.80 10 57.70 16.57 0.299 0.622 191 Comparative Example 2-1 5.40 10 38.20 12.10 0.301 0.644 32 Comparative Example 2-2 5.10 10 46.91 14.77 0.299 0.629 76 Comparative Example 2-3 5.12 10 49.05 14.90 0.298 0.630 83 Comparative Examples 2-4 5.00 10 46.63 14.50 0.300 0.631 62 Comparative Examples 2-5 5.03 10 41.10 13.11 0.298 0.629 115 Comparative Examples 2-6 5.13 10 50.95 15.00 0.298 0.629 110 Comparative Examples 2-7 5.05 10 43.85 14.55 0.297 0.630 100 Comparative Examples 2-8 5.10 10 41.00 14.10 0.302 0.633 91

[0266] As shown in Table 2 and Table 3, it can be seen that the driving voltage of the embodiment of the present invention is improved, and the efficiency is increased and the life is prolonged compared with Comparative Examples 1 to 8.

[0267] More specifically, compared with Comparative Examples 1, 2, 3, and 4 without diarylfluorene substituents, Comparative Examples 5 and 6 without fluorene linkers, Comparative Example 7 without diarylfluorene at the end, and Comparative Example 8 with bulky spirofluorene at the end, the embodiments of the present invention have diarylfluorene substituents to form HOMO suitable for the hole transport layer, and have fluorene linkers, which increase π conjugation and have fast hole mobility, have diarylfluorene at the end, thereby inducing intermolecular π stacking, making the film arrangement of molecules excellent, and improving the fluidity on the film, and have a rotatable diarylfluorene at the end to replace the bulky spirofluorene, which can improve the fluidity. Therefore, the compounds of the present invention can reduce the driving voltage of the organic light-emitting device and greatly improve the efficiency and life.

[0268] The above description of the present invention is for illustrative purposes, and a person skilled in the art of the present invention can understand that the present invention can be easily deformed in other specific ways without changing the technical concept or essential features of the present invention. Therefore, it should be understood that the multiple embodiments described above are illustrative in all aspects, rather than restrictive. For example, each structural element described in a single type can be implemented in a dispersed manner, and similarly, multiple structural elements described as dispersed can also be implemented in a combined manner.

[0269] The scope of the present invention is indicated by the attached claims for protection, rather than the above detailed description. The meaning and scope of the claims for protection and all changes or modifications derived from their equivalent concepts should be interpreted as being included in the scope of the present invention.

Claims

1. A compound, characterized in that It is represented by the following chemical formula 9: Chemical formula 9 In the chemical formula 9, Ar1 and Ar2 are each independently C1 to C 20 alkyl-substituted or unsubstituted phenyl, unsubstituted naphthyl, unsubstituted biphenyl, unsubstituted terphenyl, or unsubstituted or C1 alkyl-substituted fluorenyl, R1 to R6 are hydrogen, R and R' are each independently an unsubstituted C1 alkyl group or an unsubstituted phenyl group.

2. The compound according to claim 1, characterized in that The Ar1 and Ar2 are unsubstituted phenyl groups.

3. The compound according to claim 1, characterized in that The compound is one of the following compounds:

4. An organic light-emitting device, characterized in that: An organic layer containing the compound according to any one of claims 1 to 3 is included between the first electrode and the second electrode.

5. The organic light emitting device according to claim 4, characterized in that: The organic layer is one or more of a hole injection layer, a hole transport layer and a light-emitting auxiliary layer.

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