유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

23-01-2019 дата публикации
Номер:
KR1020190007792A
Принадлежит:
Контакты:
Номер заявки: 00-17-102089242
Дата заявки: 13-07-2017

[1]

The present invention refers to organic compound, the organic electroluminescence element and electronic device using the same are disclosed.

[2]

The means by which electrical energy using organic material generally organic light emitting phenomenon to light installed on the pipe body. Organic light emitting phenomena between an anode and a cathode and an organic solvent including an electrical element can have a conventional structure. The organic layer of this of the electrical component in order to enhance stability and multilayered structure of different material and is in many cases, e.g. hole injection layer, hole transport layer, light emitting layer, with an alkali metal-containing fullerene and can be consists of.

[3]

Materials used in the layer packed in organic electrical component to other persons, light-emitting material and a charge transporting material, such as a hole injection material, hole transporting material, an electron transport material, electron injection in order to remove can be classification.

[4]

And, according to the polymer type and said material comprises low-molecular weight can be classification, light emitting mechanism of the former along singlet fluorescent material and derived from electron triplet derived from classification phosphor material can be. In addition, according to the color of light emitted from material comprises blue, green, yellow and red light-emitting material and better color required for implementing an orange light-emitting material can be divided into.

[5]

On the other hand, as a luminescent material for one substance when only an intermolecular interaction by isolating means is moved in the long wavelength emission wavelength maximum thickness of the light emitting attenuation effect transfers can fall out of the door is reduced number, increase safety device through one or more energy transitions a luminescent dopant can be system which/in order to increase the host as a luminescent material. Energy band gap and pressure are formed in the light emitting layer host than small dopant small mixing, transported to a high efficiency light generated in a light emitting layer dopant into at 1000 ppm are disclosed. The host moves as wavelength of dopant wavelength, depending on the type of dopant using a desired light in a wavelength can be achieved.

[6]

Currently display the mayor of the electric service into its enlarged and, enemy power consumption required in portable display an existing thereby being greater than required power consumption etc.. , the battery as a power source but number having very important elements is too soon and discriminates whether the portable display power consumption, efficiency and life necessarily required number in addition door situation disclosed.

[7]

Efficiency and life, or the like may be driving voltage relative to one another, located spaced apart relatively driving voltage would increase efficiency, rotational shafts of the driving voltage falling ten which it will pick up (Joule heating) is applied as a result life can be enhanced by crystallization organic exhibits tendency. Said but simply improving efficiency by recycling a solvent that doesn't have a. However, each organic layer between T and energy level1 Value, such as the inherent properties of material (mobility, interface characteristics) when an optimal combination can be when a long life and a high efficiency are disclosed. The high thermal stability in the emissive layer efficiently charge balance (charge balance) in a predetermined region of the data in a database development of light-emitting material are disclosed.

[8]

I.e., an electron in order to fully exhibited features than the organic organic materials for the contact material, such as a hole injection material, hole transport material, luminescent material, electron transport material, stable and efficient electron injection substance or the like material supporting the parking brake and one, stable and efficient development of organic layer material sufficiently cladding organic for electrical components of the possible out-a state of exhaustion. Thus, the development of novel materials off and a continuation request, executing the developed material required in particular etc. removed.

[9]

The present invention refers to for of barrier, emitting efficiency, compounds capable of color purity on the organic layer, the organic electric element and electronic device using the same intended for a number.

[10]

In one aspect, the present invention refers to compounds represented by formula for a number substrate.

[11]

[12]

In another aspect, the present invention refers to said formula a compounds represented by using organic electric element and electronic device number substrate.

[13]

According to an embodiment of the present invention compounds may be as well as along thickness of the facing ends of the lamps, emitting efficiency, adjusting color purity and life can be remarkably improved.

[14]

Figure 1 shows a organic electroluminescent device of the present invention according to example also are disclosed.

[15]

Hereinafter, with reference to the attached drawing of the present invention in the embodiment detailed as follows.

[16]

Each of the drawings in adding references components, although other drawing even for the same components displayed on a possible code accomplishing the same may have a significantly negative. In addition, the present invention is connected to the described, publicly known or a function of the associated specific description the subject matter of invention description if a haze can be decided to be dispensed to each other.

[17]

The constitution of the invention described is provided to element, number 1, number 2, A, B, (a), (b) using terms such as can be. Other components such terms having an element discriminate between the hell of, its terms corresponding components are not limited by the nature of the or the like or sequence. Any component and other components "connected", "coupled" or "connected" are blocked when described, other components or the components thereof are connected directly but can be connected, each between components of the other components "connected", "coupled" or "connected" is a device that may be will be.

[18]

In addition, layer, film, region, a component of "on" or "on" other components such as plate changed when, as well as any other components when "directly on" another intermediate components may also include a will be that it will be used. On the contrary, if any component other portions intermediate "directly on" another motor vehicle is started without understanding that it will be.

[19]

The following is claimed as used in the specification and appended, not otherwise mentioned, for the meanings of terms to such as disclosed.

[20]

"Halo" or "halogen" is other descriptive terms used in the specification free fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) are disclosed.

[21]

The present invention "alkyl" or "alkyl group" of other terms used in the description is free carbon number 1 to 60 has a single bond, linear alkyl, branched alkyl group, a cycloalkyl (alicyclic), alkyl - substituted cycloalkyl, cycloalkyl - substituted alkyl saturated aliphatic radical of the bondable functionality including big.

[22]

The present invention "halo alkyl" or "halogen alkyl" of other terms used in the description are substituted with alkyl halogen-free big.

[23]

The present invention "alkene diary" or "alkynyl group" of other terms used in the description is in each carbon number 2 to 60 free process for preparing has, such as caprylic or side chain chain that comprises a, one number herein are not disclosed.

[24]

"Cycloalkyl" is other descriptive terms used in the present invention to free a 3 to 60 and has an alkyl carbon a number means, number herein are not disclosed.

[25]

The terms used in the present invention "alkoxy group", "alkoxy", or "alkyl jade time" means oxygen radicals and fluoroalkyl group is attached, has a carbon number of 1 to 60 other descriptive free, one number herein are not disclosed.

[26]

The present invention is oxygen radicals attached to terms used in "biting jade group" or "" means aryl which, has a carbon number of 6 to 60 other descriptive free, one number herein are not disclosed.

[27]

The present invention "fluorene diary" or "flue " of other terms used in the description in R is lower than each have battery, R 'and R "is 1 or 2 and the both are H means is functional groups," substituted fluorene "includes a substituent R, R', R" group "or" substituted the flue substituted and due at least one meaning other than hydrogen, R and R ' engage one another when they are carbon with compound cyber formed without using a tool.

[28]

[29]

The present invention "aryl" and "it will be biting, [leyn" of other terms used in the description is lower than 6 to 60 each having carbon number, the one number are not disclosed. In the present invention it will be biting and [leyn it crawls aryl group or single annular, ring assembly, bonded various ring-based, cyber compounds etc..

[30]

The present invention includes "heteroaryl group" or "hetero " used terms such as "hetero it will be biting, [leyn" as well as non-aromatic ring which may contain an aromatic ring, each including one or more heteroatoms atoms to carbon atoms is lower than other descriptive 2 means the number herein one loop of 60 or not the. The term "heteroatom" used in the specification description of other free N, O, S, P or Si exhibit, hetero ring heteroatoms including single annular, ring assembly, bonded various ring-based, cyber compounds will other.

[31]

In addition "hetero " is, instead SO carbon has an2 The system also includes a ring including can be. For example, "hetero " receive a next compound substrate.

[32]

[33]

In the present invention which comprises a unitary ring and multi annularity terms used in "ring", as well as hydrocarbon ring including at least one hetero atoms and heterocyclic, aromatic and nonaromatic ring substrate.

[34]

In the present invention terms used in "polycyclic" is biphenyl, such as separating ring assembly (ring assemblies), bonded (fused) ring systems and cyber which various compounds, aromatic as well as non-aromatic may contain, as well as heterocyclic hydrocarbon ring including at least one hetero atoms it contains.

[35]

In the present invention terms used in "ring assembly (ring assemblies)" includes two or more ring-based (single ring or bonded ring-based) single bond or double bond directly connected to each other via such ring located in a ring-based total number of directly connecting between a compound characterized by a big number 1 the dog. The same or a different ring system is single bond or double bond ring aggregates can be interconnected directly via.

[36]

In the present invention includes at least two terms used in "bonded various ring-based" sharing of atoms of the annular joint (fused) and which means, two or more of hydrocarbon ring system is junction forms thereof and at least one hetero atoms including at least one hetero ring taking count of crosses etc. bonded form. These bonding of a number of ring-based aromatic ring, a heteroaromatic ring, a combination of aliphatic or ring can be.

[37]

Terms used in "cyber compounds" in the present invention is' cyber (spiro union) connected ' has, the annulus is only 1 share of atoms of 2 connected cyber achieved by big connection. The, two ring the shared atoms' cyber to atoms' and as, according to a number of atoms so as to located in a cyber compounds to each 'mono cyber to -', 'dice to fine -', 'tri cyber to -' compound this may be.

[38]

In addition designated prefix meaning when successive order listed substituents at the first substrate means that the substrate. For example, when will be biting and the cock time which it will know which means with allyl substituted alkoxy, alkoxy substituted with alkoxy carbonyl group which when means, wherein the biting carbonyl it crawls in addition when biting carbonyl crossroad substituted alkenes which means a carbonyl substituted with allyl biting carbonyl alkene diary diary residue.

[39]

In addition without explicit description that, in the present invention in the terms used in "a substituted or unsubstituted" "substituted" deuterium, halogen, amino, nitrile, nitro, C1 - C20 Alkyl, C1 - C20 Alkoxy group, C1 - C20 Alkyl hydroxybutyrolactone, C1 - C20 Alkyl , C6 - C20 Of mote five pen it will be biting, C2 - C20 An alkenoic diary, C2 - C20 Of alkyne diary, C3 - C20 Of cyclo-alkyl, C6 - C20 Aryl, substituted with deuterium C6 - C20 Aryl, C8 - C20 Of biting alkene diary, silane, for boron, germanium for, and O, N, S, Si and P including C hetero atoms selected from the group consisting of at least one2 - C20 Heteroatoms selected from the group consisting of at least one substituted 1 ring crossroad which means, these process is provided one number are not endured.

[40]

The specification of each symbol and substituted aryl group exemplified in example, it will be biting, [leyn, such as hetero corresponding to 'name' is' to reflect hydrolysis of name 'section described, ' parent compound name ' disapproval form of the substrate. For example, in the case of electromagnetic wave is 'phenanthrene', '' 1 'to' 2 'lung difficulty [thu reel [leyn' is of is to charge such as described is for the hydrolysis of name section, regardless of a parent compound name 'phenanthrene' form of the substrate hydrolysis disapproval. Similarly, even if pyrimidine, regardless of 'pyrimidine' hydrolysis described or, if pyrimidine diary anomers 1, 2 such as in the case of hydrolysis of the corresponding pyrimidine 'name of' disapproval form of the substrate.

[41]

In addition, without explicit description that, in the present invention represented by formula formula index of definitions used by substituent definitions and equal to the received signals.

[42]

[43]

Wherein, a is an integer of 0 when R substituents1 In the absence which meaning, i.e. a benzene is 0 when combined with all of the dispersing medium has an carbon, the carbon bonded hydrogen or compounds of formula can be protruded. In addition, a is an integer from 1 whether substituent R1 Forming one of the benzene ring carbon which will bind to the carbon, for example when a is 2 or 3 can be coupled together under an integer, integer is 4 to 6 and in a similar manner even when a carbon which will bind to the benzene ring, R when a is 2 or more levels1 Or each other's personal persona disclosed.

[44]

[45]

In the embodiment according to one example of the present invention Figure 1 shows a organic electroluminescence element also are disclosed.

[46]

The reference also 1, one in the embodiment according to of the present invention organic electrical component (100) substrate (110) formed on electrode number 1 (120), number 2 electrode (180) and number 1 electrode (120) and number 2 electrode (180) between the present invention according to a solvent including compounds with each other. The, number 1 electrode (120) and the cathode (positive electrode), number 2 electrode (180) and can have a cathode (cathode), the butt style which is number 1 number 2 electrode be electrode if it will be a child node.

[47]

Organic compound layer is formed electrode number 1 (120) sequentially on hole injection layer (130), hole (140), a light emitting layer (150), alkali metal-containing fullerene (160) and with an (170) can be comprising. The, exposed to at least one of these layers, hole obstruction layer, electronic obstruction layer, light emitting (151), electronic , buffer layer (141) may further include, alkali metal-containing fullerene (160) may be provided such as peeling the electrons are serves are disclosed.

[48]

In addition, it does but not shown, in the embodiment according to number 1 and number 2 of the present invention one surface of at least one organic layer of said organic an electrical element can electrode formed on one surface opposite further includes a protective layer or optical efficiency enhancement layers (Capping layer) can be.

[49]

Said organic layer applied in the embodiment according to one of the present invention compounds are hole injection layer (130), hole (140), light emitting (151), electronic , alkali metal-containing fullerene (160), with an (170) of a material such as, light emitting layer (150) host or doping material, or light efficiency improving layer may be formed by using are disclosed. For example, the light emitting layer of the present invention compound (150), hole (140) and/or a light emitting (151) can be formed by using, preferably light emitting layer (150) can be used as a host material.

[50]

On the other hand, even the same core which is a methyl substituent coupling along band gap (band gap), electrical characteristics, interface characteristics may change is, for selecting and coupled subsystems are coupled to core (sub)- forward and for each combination of substituents, in particular energy level between T and each organic layer1 Value, such as the inherent properties of material (mobility, interface characteristics) when a long life and a high efficiency when an optimal combination can be.

[51]

Thus, in the present invention formula 1 using compound having a light-emitting layer (150) between each organic layer by forming energy level and T1 Value, the inherent properties of material such as organic electroluminescence (mobility, interface characteristics) can be simultaneously improving of prolonging the life and efficiency is optimized.

[52]

The organic electroluminescent device in the embodiment according to one of the present invention various deposition (deposition) number in an bath using are disclosed. PVD or CVD method can be provided on the tank which number using, for example, depositing a metal film on the substrate or conductive metal oxides or alloys thereof anodes (120) is formed, on the hole injection layer (130), hole (140), a light emitting layer (150), alkali metal-containing fullerene (160) and with an (170) including a layer is formed on the organic, for the plurality (180) by depositing a material which can be use number bath 1308. In addition, hole (140) and a light-emitting layer (150) light emitting (151) a, light emitting layer (150) and alkali metal-containing fullerene (160) further can be formed between electronic transportation cadence layer.

[53]

In addition, various organic compound layer is formed polymer solution or solvent (solvent process) not a material deposition process, such as spin coating process, nozzle printing, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor steam turbines process, screen printing process, or thermal transfer method such as number of layer number can be by means of a high pressure liquid coolant. The present invention according to ITO layers can be formed into various method first, forming method of the present invention by the number range rights are not the.

[54]

In the embodiment according to materials used in the formed at each-emitting organic an electrical element can one of the present invention, can be a backlit or two-sided light emitting type.

[55]

And exhibits excellent processability for high resolution achieved by the WOLED (White Organic Light Emitting Device) is hereinafter, color filter is detected by the number of LCD can be bath...copyright 2001. White backlight device to perform various structures are mainly used as blue light emission and to perish patent number etc. and stored. Typically, R (Red), G (Green), B (Blue) light emitting portions disposed in parallel each other in a way that the (side provided by a-side), R, G, B down (stacking) and luminescent layer lamination scheme, blue (B) and inorganic phosphor converts the organic electro-luminescent in luminous layer therefrom light (photo-a luminescence) color (color conversion material, CCM) such as using the ends of the annular material, also be applied to the present invention refers to such WOLED S802.

[56]

In addition, in the embodiment according to one of the present invention organic an electrical element can organic electroluminescence device, organic solar cells, organic photoreceptor, organic transistor, one white lighting element can be monochrome or color.

[57]

In the embodiment of the present invention is device including an electrical component on the aforementioned of the present invention other organic display, the display device comprising a number plower number including electronic device can be a water level. The, current or future electronic device is wire communication terminal may be, of a mobile phone, PDA, electronic dictionary, PMP, remote control, navigation, game machine, various TV, all electronic device comprising the various personal computer or the like.

[58]

Hereinafter, according to one aspect of the present invention compounds are disclosed therein.

[59]

According to one aspect of the present invention represented by formula 1 is displayed to.

[60]

<>Formula 1

[61]

[62]

In said formula 1 can be reacted with under each symbol.

[63]

R1 To R12 Are each independently a hydrogen; deuterium; halogen; C6 - C60 Aryl; fluorene diary; O, N, S, Si and at least one of the hetero atoms including C P2 - C60 A variety of ; C3 - C60 C aliphatic ring and6 - C60 An aromatic ring in a fusion ; C1 - C50 Alkyl; C2 - C20 An alkenoic diary; C2 - C20 Of alkyne diary; C1 - C30 The alkoxylation group; C6 - C30 Of ; and - L' - N (Ra ) (Rb ); Selected from the group consisting of, forms a ring combination can be adjacent to each other.

[64]

R1 To R12 When is it is an allyl, preferably C6 - C30 Aryl, more preferably C6 - C14 Aryl, specifically, phenyl, biphenyl, naphthalene, phenanthrene etc. disclosed. R1 To R12 When heterocyclic is due, preferably C2 - C30 heteroatoms, more preferably C2 - C12 A variety of , specifically pyrimidine, triazine, carbazole etc. disclosed.

[65]

R1 To R12 Adjacent to each other in the annular C combination6 - C60 Aromatic hydrocarbon, O, N, S, Si and at least one of the hetero atoms including C P2 - C60 Can be heterocyclic or fluorene and the like, specifically benzene, naphthalene, phenanthrene etc. disclosed.

[66]

The X ring C6 - C60 Aromatic hydrocarbon; fluorene; O, N, S, Si and at least one of the hetero atoms including C P2 - C60 N-heterocyclic; and C3 - C60 C aliphatic ring and6 - C60 An aromatic ring in a fused ring; selected from the group consisting of.

[67]

When X is aromatic hydrocarbon ring, preferably C6 - C30 Aromatic hydrocarbon, more preferably C6 - C18 Aromatic hydrocarbon, specifically benzene, biphenyl, naphthalene, phenanthrene, triphenylene, fine alkylene, fluoranthene etc. disclosed. When the heterocyclic ring X, preferably C2 - C30 N-heterocyclic, more preferably C2 - C24 N-heterocyclic, specifically pyridine, pyrimidine, rho kinase, pyridazine, quinoline, quinoxaline, quinazoline, benzo quinazoline, die benzo quinazoline, benzo be enveloped the pen, benzofuran, indole, die , benzo my [phu toe be enveloped the pen, it cuts trillion [phyu column die, benzo , carbazole, benzo it is cheap hereupon roh blood america [tin, with [phyu blood america [tin benzo, pyridazinone anti indole, 1, 1 - methyl - 1H - indene, pyrimido , imidazopyridine, imidazoquinolines, disclosed hereinafter synchronized, disclosed hereinafter substituted, phenyl phenoxy photo, phenyl roh lung is cheap oh position, inside [thu cycle, die benzo dioxin, naphthyridine, benzo , benzo , benzo etc. disclosed. When five [leyn is the X ring and process for preparation thereof, 9 - diphenyl - 9H - fluorene, 9, 9' - with at all [phul base five [leyn cyber etc. disclosed.

[68]

Said L'is single bond; C6 - C60 It will be biting, [leyn of; the flue ; C3 - C60 C aliphatic ring and6 - C60 An aromatic ring in a fusion ; and C2 - C60 A variety of ; can be selected from the group consisting of.

[69]

Said Ra And Rb C independently of each other6 - C60 Aryl; fluorene diary; C3 - C60 C aliphatic ring and6 - C60 An aromatic ring in a fusion ; and O, N, S, Si and at least one of the hetero atoms including C P2 - C60 A variety of ; can be selected from the group consisting of.

[70]

Said aryl group, it will be biting, [leyn, aromatic hydrocarbons, fluorene diary, the flue , fluorene, hetero , heterocyclic, fusion , fused ring, alkyl group, alkenyl group, alkynyl group, alkoxy, , and R1 - R12 An annular combination adjacent to each other during each deuterium; halogen; C1 - C20 C phenyl or benzyl6 - C20 With allyl substituted or substituted or unsubstituted silane of; a siloxane group; to boron; for germanium; cyano group; nitro; C1 - C20 Alkyl ; C1 - C20 The alkoxylation group; C1 - C20 Alkyl; C2 - C20 An alkenoic diary; C2 - C20 Of alkyne diary; C6 - C20 Aryl; substituted with deuterium C6 - C20 Aryl; fluorene diary; O, N, S, Si and P including C hetero atoms selected from the group consisting of at least one2 - C20 A variety of ; C3 - C20 Of cyclo-alkyl; C7 - C20 Of aryl-alkyl; C8 - C20 Of biting alkene diary; - L' - N (Ra ) (Rb ); And combination thereof one or more selected from the group consisting substituted can be further substituted, wherein L', Ra And Rb Is defined in said such as disclosed.

[71]

Represented by said formula 1 can be represented by formula 2.

[72]

<>Formula 2

[73]

[74]

In said formula 2, R1 To R12 Is as defined in formula 1 and, X1 To X4 Are each independently N, C (R '), N (R'), S, O or C (R ') (R ") and, m is 0 or 1 are disclosed.

[75]

Said R ' and R " independently of each other hydrogen; deuterium; halogen; C1 - C20 C phenyl or benzyl6 - C20 With allyl substituted or substituted or unsubstituted silane of; a siloxane group; to boron; for germanium; cyano group; nitro; C1 - C20 Alkyl ; C1 - C20 The alkoxylation group; C1 - C20 Alkyl; C2 - C20 An alkenoic diary; C2 - C20 Of alkyne diary; C6 - C20 Aryl; substituted with deuterium C6 - C20 Aryl; fluorene diary; O, N, S, Si and P including C hetero atoms selected from the group consisting of at least one2 - C20 A variety of ; C3 - C20 Of cyclo-alkyl; C7 - C20 Of aryl-alkyl; C8 - C20 Of biting alkene diary; - L' - N (Ra ) (Rb ); And combinations thereof selected from the group consisting, adjacent R ' can be each in combination forms a ring.

[76]

Ra And Rb When is it is an allyl, preferably C6 - C30 Aryl, more preferably C6 - C14 Aryl, specifically, phenyl, biphenyl, naphthalene, phenanthrene etc. disclosed. Ra And Rb When heterocyclic is due, preferably C2 - C30 heteroatoms, more preferably C2 - C12 A variety of , specifically die it cuts trillion [phyu column, die etc. disclosed. Ra And Rb The flue is when they are five [leyn diaries, 9 - methyl - 9H - fluorene, 9 - diphenyl - 9H - fluorene, 9, 9' - with at all [phul base five [leyn cyber etc. disclosed.

[77]

Said formula 2 is represented by formula 3 or formula 4 to can be.

[78]

<><>Formula 3 formula 4

[79]

[80]

In said formula 3 and formula 4, R1 To R12 , And X1 To X4 Is defined in formula 2 as disclosed.

[81]

In addition, represented by said formula 1 to formula 18 can be display one of formula 5.

[82]

<><>Formula 5 formula 6 <>Formula 7

[83]

[84]

Formula 8<><>formula 9 <>Formula 10

[85]

[86]

Formula 11<><>formula 12 <>Formula 13

[87]

[88]

Formula 15>><<formula 14 <>Formula 16

[89]

[90]

<>Formula 17 <>Formula 18

[91]

[92]

In said formula 5 to formula 18, R1 To R12 , And X1 To X4 Is defined in formula 2 as disclosed.

[93]

X5 To X33 N independently of each other, C (R '), N (R'), S, O or C (R ') (R ") and, Y1 And Y2 Are each independently N (R '), S, O or C (R') (R ") and, wherein R ' is defined in formula 2 as disclosed.

[94]

Specifically, one of compounds can be represented by said formula 1.

[95]

[96]

[97]

[98]

[99]

In another aspect of the present invention, electrode the present invention refers to number 1, number 2 electrode, and said number 1 and number 2 electrode positioned between the organic solvent including electrical elements number substrate. The, said organic compound layer is formed by means of said formula 1 compound.

[100]

Said organic compound layer is formed hole injection layer, hole transport layer, light emitting , light emitting layer, electronic , with an alkali metal-containing fullerene and at least one of layer comprising, formula 1 compound having a hole injection layer, hole transport layer, light emitting , light emitting layer, electronic , with an alkali metal-containing fullerene and at least one of layer that can be, preferably said light emitting layer can be included. The, at least one compound or a mixture of said compounds are 1 species alone 2 can be in the form of a, preferably compounds represented by said formula 1 removed material, in particular can be used as phosphorescent red-host material.

[101]

In hereinafter, the present invention according to formula 1 in the embodiment of the electrical component with respect to the synthesis of compound number for example specifically described attainments organic and positive examples but, in the embodiment of the present invention is confined to not the.

[102]

[103]

Synthesis example

[104]

Illustratively the present invention according to formula 1 compound is a compound 1 or compound 2 (Final Products) can be bath such as number or, limited to are not correct.

[105]

1><Reactive

[106]

[107]

2><Reactive

[108]

[109]

Sub 1 synthesis of

[110]

1 Reactive Sub 1 of 3 can be synthesized by reaction of path is a compound defined are not correct.

[111]

3><Reactive

[112]

[113]

Synthesis of Sub 1 - 1

[114]

(1) Synthesis of Sub 1 a-I

[115]

[116]

Starting material 2, 7 a-dibromonaphthalene (40. 0 G, 139. 9 Mmol) to a THF 700 ml into a seam sealing, (2 a-nitrophenyl) boronic acid (51. 4 G, 307. 7 Mmol), Pd (PPh3 )4 (4. 9 G, 4. 2 Mmol), K2 CO3 (58. 0 G, 419. 6 Mmol), adding 80 °C-gate 300 ml water with agitation. Reaction is complete CH2 Cl2 After extracting a MgSO on organic layer4 After the resulting compound and concentrated to dry silicagel column and subsequent recrystallization product 42. 2 G (yield: 84%) are obtained.

[117]

(2) Synthesis of Sub 1 - 1

[118]

[119]

Said Sub 1 a-I obtained in the synthesis (42. 2G, 113. 9 Mmol) DMF 570 ml into a to seam sealing, PPh3 (89. 9 G, 341. 8 Mmol) added with agitation-gate 165 °C. Reaction is complete CH2 Cl2 After extracting a MgSO on organic layer4 After the resulting compound and concentrated to dry silicagel column and subsequent recrystallization product 25. 5 G (yield: 73%) are obtained.

[120]

Synthesis of Sub 1 - 7

[121]

[122]

(1) Synthesis of Sub 1 a-II-a 1

[123]

2 A-bromo-a 9 a-iodophenanthrene starting material (30. 0 G, 78. 3 Mmol) and (10 a-nitrophenanthren provided 9 a-yl) boronic acid (23. 01 G, 86. 16 Mmol) using the method of synthesizing said Sub 1 a-I product 30. 1 G (yield: 80%) are obtained.

[124]

(2) Synthesis of Sub 1 a-II

[125]

Sub 1 a-II-a 1 (30. 0 G, 62. 7 Mmol) and (2 a-nitrophenyl) boronic acid (11. 5 G, 69. 0 Mmol) using the method of synthesizing said Sub 1 a-I product 24. 2 G (yield: 74%) are obtained.

[126]

(3) Synthesis of Sub 1 - 7

[127]

Sub 1 a-II(24. 0 G, 46. 1 Mmol) using a method of synthesizing said Sub 1 - 1 product 15. 6 G (yield: 74%) are obtained.

[128]

Synthesis of Sub 1 - 11

[129]

[130]

(1) Synthesis of Sub 1 a-III-a 1

[131]

Sub 1 - 1 (20. 0 G, 65. 3 Mmol) to a DMF 350 ml seam sealing, NBS (N n-bromosuccinimide (12. 8 G, 71. 8 Mmol) is added at room temperature stirring time-gate 6. Reaction terminates after the separation of the organic layer MgSO4 After the resulting compound and concentrated to dry silicagel column and subsequent recrystallization product 19. 8 G (yield: 79%) are obtained

[132]

(2) Synthesis of Sub 1 - 11

[133]

Sub 1 a-III-a 1 (18. 0 G, 62. 7 Mmol) and phenanthren provided 3 provided ylboronic acid (11. 4 G, 51. 4 Mmol) using the method of synthesizing said Sub 1 a-I product 17. 5 G (yield: 78%) are obtained.

[134]

Synthesis of Sub 1 - 13

[135]

[136]

(1) Synthesis of Sub 1 a-IV-a 1

[137]

Starting material 2 a-bromo-a 7 a-iodonaphthalene (30. 0 G, 90. 1 Mmol) and (4 a-chloro-a 2 non-nitrophenyl) boronic acid (20. 0 G, 99. 1 Mmol) using the method of synthesizing said Sub 1 a-I product 27. 7 G (yield: 85%) are obtained.

[138]

(2) Sub 1 a-IV-a 2 synthesis

[139]

Sub 1 a-IV-a 1 (25. 0 G, 68. 9 Mmol) and (2 a-nitrophenyl) boronic acid (12. 7 G, 75. 8 Mmol) using the method of synthesizing said Sub 1 a-I product 22. 2 G (yield: 80%) are obtained.

[140]

(3) Sub 1 a-IV-a 3 synthesis

[141]

Sub 1 a-IV-a 2 (20. 0 G, 49. 4 Mmol) using a method of synthesizing said Sub 1 - 1 product 10. 1 G (yield: 60%) are obtained.

[142]

(4) Synthetic Sub 1 - 13

[143]

Sub 1 a-IV-a 3 (10. 0 G, 29. 3 Mmol) and (9 - (4, 6 a-diphenyl-a 1, 3, 5 a-triazin-a 2 a-yl) - 9H-a carbazol-a 2 a-yl) boronic acid (14. 3 G, 32. 3 Mmol) using the method of synthesizing said Sub 1 a-I product 15. 5 G (yield: 75%) are obtained

[144]

[145]

Sub 1 by the following example is as follows but included, limited to are not correct. Table 1 is a illustrative Sub 1 included in compounds that represents the value of FD-a MS (Field Desorption provided Mass Spectrometry) are disclosed.

[146]

[147]

[Table 1]

[148]

[149]

[150]

Sub 2 of Synthesis example

[151]

Of belonging to compound that is synthesized by reaction of reactive 1 Sub 2 can be defined in the path are not correct.

[152]

Synthesis of example Sub 2 - 19

[153]

[154]

Round bottom cap to 2, 3 a-dichloro-a 9H-a carbazole (15. 0 G, 63. 5 Mmol) frame and toluene (300 ml) to a seam sealing 2 a-bromo-a 4 a-phenylquinazoline (23. 5 G, 82. 6 Mmol), Pd2 (Dba)3 (1. 75 G, 1. 9 Mmol), P (t- Bu)3 (0. 8 G, 3. 8 Mmol), NaOt- Bu (18. 3 G, 190. 6 Mmol) followed by addition of 100 °C-gate in order with agitation. After the reaction is completed on MgSO ether extracting organic layer4 After the resulting compound and concentrated to dry silicagel column and subsequent recrystallization product 21. 5 G (yield: 77%) are obtained.

[155]

Synthesis of example Sub 2 - 39

[156]

[157]

2, 3 A-dichloro-a 1H-a indole (14. 0 G, 75. 3 Mmol) and 2 a-bromo-a 3 a-phenylquinoxaline (27. 9 G, 97. 8 Mmol) using the method of synthesizing said Sub 2 - 19 product 22. 2 G (yield: 76%) are obtained.

[158]

Synthesis of example Sub 2 - 50

[159]

[160]

Triphenylen provided 2 a-ylboronic acid (13. 3 G, 48. 7 Mmol) and 4 a-bromo-a 1, 2 a-dichlorobenzene (10. 0 G, 44. 3 Mmol) using the method of synthesizing said Sub 1 a-I product 11. 9 G (yield: 72%) are obtained.

[161]

Synthesis of example Sub 2 - 66

[162]

[163]

Bromobenzene (9. 7 G, 61. 7 Mmol) and 3, 4 a-dichloroaniline (5. 0 G, 30. 9 Mmol) using the method of synthesizing said Sub 2 - 19 product 7. 2 G (yield: 74%) are obtained.

[164]

[165]

Sub 2 by the following example is as follows but included, limited to are not correct. Table 2 is an illustrated Sub 2 included compounds to FD-a MS represents the value of a (Field Desorption provided Mass Spectrometry) are disclosed.

[166]

[167]

[168]

[Table 2]

[169]

[170]

[171]

[172]

Final compounds Synthesis example

[173]

P-a 3 synthesis example

[174]

[175]

Sub 1 - 1 (4. 6 G, 15. 0 Mmol) into a toluene (100 ml) to a seam sealing, Sub 2 - 3 [Cas. 2050 - 75 - 1] (3. 0 G, 15. 0 Mmol), Pd2 (Dba)3 (0. 4 G, 0. 5 Mmol), P (t- Bu)3 (0. 2 G, 0. 9 Mmol), NaOt- Bu (4. 3 G, 45. 0 Mmol) added with agitation 100 °C-gate. Reaction is complete CH2 Cl2 After extracting a MgSO on organic layer4 After the resulting compound and concentrated to dry silicagel column and subsequent recrystallization product 3. 5 G (yield: 54%) are obtained.

[176]

P-a 19 synthesis example

[177]

[178]

Sub 1 - 1 and (5. 5 G, 18. 0 Mmol) and Sub 2 - 19 (18. 0 G, 7. 9 Mmol) using the method of synthesizing said P-a 3 product 7. 2 G (yield: 60%) are obtained.

[179]

P-a 26 synthesis example

[180]

[181]

Sub 1 - 1 and (4. 8 G, 15. 7 Mmol) and Sub 2 provided 26 [Cas No. 2213 - 63 - 0] (3. 1 G, 15. 7 Mmol) using the method of synthesizing said P-a 3 product 3. 9 G (yield: 58%) are obtained.

[182]

P-a 27 synthesis example

[183]

[184]

Sub 1 - 1 and (4. 1 G, 13. 4 Mmol) and Sub 2 provided [27 Cas No. 26907 - 93 - 7] (3. 3 G, 13. 4 Mmol) using the method of synthesizing said P-a 3 product 3. 5 G (yield: 54%) are obtained.

[185]

P-a 39 synthesis example

[186]

[187]

Sub 1 - 1 and (4. 6 G, 15. 0 Mmol) Sub 2 - 39 and (5. 9 G, 15. 0 Mmol) using the method of synthesizing said P-a 3 product 6. 5 G (yield: 69%) are obtained.

[188]

P provided 46 synthesis example

[189]

[190]

Sub 1 - 7 and (5. 5 G, 12. 0 Mmol) and Sub 2 provided 45 [Cas No. 4926 - 53 - 8] (2. 3 G, 12. 0 Mmol) using the method of synthesizing said P-a 3 product 4. 2 G (yield: 62%) are obtained.

[191]

P-a 50 synthesis example

[192]

[193]

Sub 1 - 11 and (5. 6 G, 11. 6 Mmol) and Sub 2 provided [1 Cas No. 95 - 50 - 1] (1. 7 G, 11. 6 Mmol) using the method of synthesizing said P-a 3 product 4. 2 G (yield: 66%) are obtained.

[194]

P-a 52 synthesis example

[195]

[196]

Sub 1 - 13 and (4. 9 G, 7. 0 Mmol) and Sub 2 provided [1 Cas No. 95 - 50 - 1] (1. 0 G, 7. 0 Mmol) using the method of synthesizing said P-a 3 product 2. 7 G (yield: 50%) are obtained.

[197]

P-a 58 synthesis example

[198]

[199]

Sub 1 - 1 and (6. 6 G, 21. 5 Mmol) and Sub 2 - 50 (8. 0 G, 21. 5 Mmol) using the method of synthesizing said P-a 3 product 8. 2 G (yield: 63%) are obtained.

[200]

P-a 74 synthesis example

[201]

[202]

Sub 1 - 1 and (3. 9 G, 12. 7 Mmol) Sub 2 - 66 and (4. 0 G, 12. 7 Mmol) using the method of synthesizing said P-a 3 product 4. 6 G (yield: 66%) are obtained.

[203]

P-a 83 synthesis example

[204]

[205]

Sub 1 - 1 and (4. 4 G, 14. 4 Mmol) and Sub 2 provided 75 [Cas No. 943611 - 33 - 4] (4. 1 G, 14. 4 Mmol) using the method of synthesizing said P-a 3 product 4. 6 G (yield: 62%) are obtained.

[206]

P-a 94 synthesis example

[207]

[208]

Sub 1 - 1 and (5. 5 G, 18. 0 Mmol) and Sub 2 provided 86 [Cas No. 164471 - 02 - 7] (6. 3 G, 18. 0 Mmol) using the method of synthesizing said P-a 3 product 6. 1 G (yield: 58%) are obtained.

[209]

[210]

The final compounds according to table 3 is generated to said synthesis represents the value of FD-a MS (Field Desorption provided Mass Spectrometry) are disclosed.

[211]

[Table 3]

[212]

[213]

[214]

[215]

Number of the electrical component trillion phyengs (1 phyeng=3.954 square yards) organic

[216]

[In the embodiment 1] Red Organic electroluminescence device (phosphorescent host)

[217]

ITO layer formed on glass substrate (anode) 4, 4 ', 4 "- Tris [2 a-naphthyl (phenyl) amino] triphenylamine (hereinafter" 2 a-TNATA "to being shrewd, by) film vacuum deposition to 60 nm thickness of hole-injecting layer is formed, 4, 4' - bis [N - (1 a-naphthyl) - N non-phenylamino] biphenyl (hereinafter" NPD " by being shrewd, to) vacuum deposition film thickness 60 nm by a chemical formula weight percent. Then, the present invention compound on said host material a hole P provided 1, dopant material bis - (1 a-phenylisoquinolyl) iridium (III) acetylacetonate (hereinafter " (piq)2 Ir (acac)" as by being shrewd,) to form the layer by doping using 95:5 weight ratio was 30 nm thickness. Then, said light emitting layer on the hole obstruction layer (1, 1' - biphenyl-a 4 a-olato) bis (2 a-methyl-a 8 a-quinolinolato) aluminum vacuum deposition (hereinafter "BAlq" by being shrewd, to) and a 10 nm thickness, said alkyl group on hole obstruction layer tris - (8 a-hydroxyquinoline) aluminum (hereinafter " Alq3 " By being shrewd, to) 40 nm thickness was a vacuum deposition. Then, a LiF 0 [ceyn anger in a halo with an alkali metal. 2 Nm evaporation method, then a negative electrode has a thickness of 150 nm by forming a Al depositing organic electroluminescent device number was high pressure liquid coolant.

[218]

[In the embodiment 2] To [In the embodiment 34]

[219]

Compounds of the present invention removed material on behalf of the present invention compounds 4 P-a 1 a bright point number said in the embodiment 1 and the same method number organic electroluminescent device was high pressure liquid coolant.

[220]

[Comparison example 1] And [Comparison example 2]

[221]

Compounds of the present invention removed material for comparison compound A or comparative compound B P-a 1 instead of using the same method and organic electroluminescent device number number point said in the embodiment 1 was high pressure liquid coolant.

[222]

A comparison compound B><><comparison compounds

[223]

[224]

In the embodiment 34 of the present invention in the embodiment 1 to, comparison example 1 and comparison example 2 allow the organic electroluminescent device prepared by the number by applying direct current to the electroluminescent (EL) research (photoresearch) yarn is irradiated for measuring a characteristic when the PR-a 650, 2500 cd/m2 In reference number in parts of equipment when the measuring life through T95 produced therewith, represented table 4 measurement such as disclosed.

[225]

[Table 4]

[226]

[227]

[228]

From the result of said table 4 you will, phosphorescence lake strobe light emitting material for organic electroluminescence device using the organic electroluminescence device of the present invention, smaller than the gate-on voltage inverse life are improved. I.e., host material CBP or employed primarily in comparison compound A, host B compounds of the present invention formula 1 are similar comparison is used as a material of the present invention is used as a material when compared to host compounds, organic electroluminescent emitting efficiency, smaller than the gate-on voltage inverse life are improved.

[229]

This novel structure of the present invention compared to a suitable comparison compounds of HOMO, LUMO energy bottom by light emitting layer and the electrons in charge balance (charge balance) because of increased as shown substrate.

[230]

According to the present invention description is to exemplify the user connects to the more generally described, the present invention is provided having essentially the consultation NaOCl inputted from deviating from various deformable properties of the present invention will. Thus, the specification is to define the present invention disclosure but rather to explain the in the embodiment are and, in the embodiment of the present invention by such range is defined in which event are not correct. The claims of the present invention scope of protection must be interpreted by below, all techniques of the present invention in a range equal to the range including rights will be interpreted.

[231]

100: Organic electrical component 110: Substrate 120: Number 1 electrode 130: Hole injection layer 140: Hole 141: Buffer layer 150: Light emitting layer 151: Light emitting 160: Alkali metal-containing fullerene 170: With an 180: Number 2 electrode



[232]

Disclosed are a compound represented by a formula 1, an organic electronic element having a first electrode, a second electrode, and an organic matter layer between the first electrode and the second electrode, and an electronic device thereof. The compound represented by the formula 1 is contained in the organic matter layer to reduce driving voltage of the organic electronic element and improve light emitting efficiency and durability.<br>COPYRIGHT KIPO 2019<br>



A compound having a formula 1:<>formula 1 In said formula 1, R1 To R12 Are each independently a hydrogen; deuterium; halogen; C6 - C60 Aryl; fluorene diary; O, N, S, Si and at least one of the hetero atoms including C P2 - C60 A variety of ; C3 - C60 C aliphatic ring and6 - C60 An aromatic ring in a fusion ; C1 - C50 Alkyl; C2 - C20 An alkenoic diary; C2 - C20 Of alkyne diary; C1 - C30 The alkoxylation group; and C6 - C30 Of ; and - L' - N (Ra ) (Rb ); Selected from the group consisting of, forms a ring combination can be adjacent to each other, the X ring C6 - C60 Aromatic hydrocarbon; fluorene; O, N, S, Si and at least one of the hetero atoms including C P2 - C60 N-heterocyclic; and C3 - C60 C aliphatic ring and6 - C60 An aromatic ring in a fused ring; selected from the group consisting of, said L'is single bond; C6 - C60 It will be biting, [leyn of; the flue ; C3 - C60 C aliphatic ring and6 - C60 An aromatic ring in a fusion ; and C2 - C60 A variety of ; selected from the group consisting of, said Ra And Rb C independently of each other6 - C60 Aryl; fluorene diary; C3 - C60 C aliphatic ring and6 - C60 An aromatic ring in a fusion ; and O, N, S, Si and at least one of the hetero atoms including C P2 - C60 A variety of ; selected from the group consisting of, said aryl group, it will be biting, [leyn, aromatic hydrocarbons, fluorene diary, the flue , fluorene, hetero , heterocyclic, fusion , fused ring, alkyl group, alkenyl group, alkynyl group, alkoxy, , R1 - R12 An annular combination adjacent to each other during each deuterium; halogen; C1 - C20 C phenyl or benzyl6 - C20 With allyl substituted or substituted or unsubstituted silane of; a siloxane group; to boron; for germanium; cyano group; nitro; C1 - C20 Alkyl ; C1 - C20 The alkoxylation group; C1 - C20 Alkyl; C2 - C20 An alkenoic diary; C2 - C20 Of alkyne diary; C6 - C20 Aryl; substituted with deuterium C6 - C20 Aryl; fluorene diary; O, N, S, Si and P including C hetero atoms selected from the group consisting of at least one2 - C20 A variety of ; C3 - C20 Of cyclo-alkyl; C7 - C20 Of aryl-alkyl; C8 - C20 Of biting alkene diary; - L' - N (Ra ) (Rb ); And combination thereof one or more selected from the group consisting substituted can be further substituted.

According to Claim 1, characterized in that said formula 1 is a compound represented by formula 2:<>formula 2 In said formula 2, R1 To R12 According to Claim 1 is such as defined and, X1 To X4 Are each independently N, C (R '), N (R'), S, O or C (R ') (R ") and, m is 0 or 1 and, said R' and R" independently of each other hydrogen; deuterium; halogen; C1 - C20 C phenyl or benzyl6 - C20 With allyl substituted or substituted or unsubstituted silane of; a siloxane group; to boron; for germanium; cyano group; nitro; C1 - C20 Alkyl ; C1 - C20 The alkoxylation group; C1 - C20 Alkyl; C2 - C20 An alkenoic diary; C2 - C20 Of alkyne diary; C6 - C20 Aryl; substituted with deuterium C6 - C20 Aryl; fluorene diary; O, N, S, Si and P including C hetero atoms selected from the group consisting of at least one2 - C20 A variety of ; C3 - C20 Of cyclo-alkyl; C7 - C20 Of aryl-alkyl; C8 - C20 Of biting alkene diary; - L' - N (Ra ) (Rb ); And combinations thereof selected from the group consisting, adjacent R ' can be each in combination forms a ring.

According to Claim 1, formula 3 is a compound characterized display of one of said formula 1 to formula 18:<><>formula 3 formula 4 <><>Formula 5 formula 6 <>Formula 7 Formula 8<><>formula 9 <>Formula 10 Formula 11<><>formula 12 <>Formula 13 Formula 15>><<formula 14 <>Formula 16 <>Formula 17 <>Formula 18 In said formula 3 to formula 18, R1 To R12 According to Claim 1 is such as defined and, X1 To X33 N independently of each other, C (R '), N (R'), S, O or C (R ') (R ") and, Y1 And Y2 Are each independently N (R '), S, O or C (R') (R ") and, said R ' and R" independently of each other hydrogen; deuterium; halogen; C1 - C20 C phenyl or benzyl6 - C20 With allyl substituted or substituted or unsubstituted silane of; a siloxane group; to boron; for germanium; cyano group; nitro; C1 - C20 Alkyl ; C1 - C20 The alkoxylation group; C1 - C20 Alkyl; C2 - C20 An alkenoic diary; C2 - C20 Of alkyne diary; C6 - C20 Aryl; substituted with deuterium C6 - C20 Aryl; fluorene diary; O, N, S, Si and P including C hetero atoms selected from the group consisting of at least one2 - C20 A variety of ; C3 - C20 Of cyclo-alkyl; C7 - C20 Of aryl-alkyl; C8 - C20 Of biting alkene diary; - L' - N (Ra ) (Rb ); And combinations thereof selected from the group consisting, adjacent R 'can be each in combination forms a ring, said L', Ra And Rb Is defined according to Claim 1 such as disclosed.

According to Claim 1, characterized in that said formula 1 is a compound one of compounds: .

Number 1 electrode; number 2 electrode; and said number 1 and number 2 defined between electrode, an organic layer containing any one of Claim 1 to Claim 4; including the organic electroluminescence element.

According to Claim 5, 1 2 compound or a mixture of said compounds are in the form of at least one species alone is characterized by the electrical component.

According to Claim 5, said organic compound layer is formed hole injection layer, hole transport layer, light emitting , light emitting layer, electronic , characterized with an alkali metal-containing fullerene and at least one of the layer including the organic element.

According to Claim 7, said compounds are said red phosphorescent host material of the emitting layer used is characterized by electrical component.

According to Claim 5, said organic compound layer is formed spin coating process, nozzle printing, inkjet printing process, slot coating process, formed by dip coating process or roll-to-roll process is characterized by the electrical component.

Organic electroluminescence display device according to Claim 5 including element; and said display device driving control section number; a including electronic device.

According to Claim 10, said organic an electrical element can organic electroluminescence device, organic solar cells, organic photoreceptor, organic transistor, and monochrome or white lighting element characterized in one of the electronic device.