Compound and organic electroluminescent device comprising the same

Abstract

The present invention relates to a specific compound, a material for an organic electroluminescent device, preferably an emitter material, comprising said specific compound, an organic electroluminescent device comprising said specific compound, an electronic device comprising said organic electroluminescent device, a light emitting layer comprising at least one host and at least one dopant, wherein the dopant comprises at least one of said specific compounds, and the use of said compounds in organic electroluminescent devices. # imgabs0 # wherein at least one of R21, R22 and R23 represents a group HAr; hAr is a group of formula (II) # imgabs1 #

Description

[0001] The present invention relates to a specific compound, a material for an organic electroluminescent device comprising the specific compound, preferably an emitter material, an organic electroluminescent device comprising the specific compound, an electronic device comprising the organic electroluminescent device, a light emitting layer comprising at least one host and at least one dopant, wherein the dopant comprises at least one of the specific compounds, and use of the compound in an organic electroluminescent device.

[0002] When voltage is applied to an organic electroluminescent device (hereinafter may be referred to as an organic EL device), holes are injected from the anode into the emission layer, and electrons are injected from the cathode into the emission layer. In the emission layer, the injected holes and electrons recombine and form excitons.

[0003] The organic EL device includes an emission layer between an anode and a cathode. In addition, there may be a case where it has a stacked layer structure including organic layers such as a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and the like.

[0004] US2022 / 0020925 A1 and US2021 / 0066599 A1 each relate to a compound represented by the following formula (1), wherein R 12 To R 28 One of them is bonded to L2.

[0005]

[0006] R1 to R2 do not form a substituted or unsubstituted, saturated or unsaturated ring 11 , and R which does not form a substituted or unsubstituted, saturated or unsaturated ring and is not bonded to L2 12 to R19 are especially independently a hydrogen atom, a substituted or unsubstituted alkyl group comprising 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group comprising 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group comprising 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group comprising 2 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group comprising 3 to 50 carbon atoms forming a ring.

[0007] US2021 / 0062078 A1 relates to a compound represented by the following formula (1), wherein in formula (1), at least one of R1 to R8 is a group represented by the following formula (2).

[0008]

[0009] -L1-HAr (2)

[0010] R1 to R2 do not form a substituted or unsubstituted, saturated or unsaturated ring 11 , and R 12 and R13 In particular, they are independently a hydrogen atom, a substituted or unsubstituted alkyl group comprising 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group comprising 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group comprising 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group comprising 2 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group comprising 3 to 50 carbon atoms forming a ring.

[0011] WO2021049889 A1 relates to a compound represented by the following formula (1):

[0012] in

[0013] Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; or represented by the following formula (2),

[0014] in

[0015] When Y is represented by Formula 2, at least one of X1, X2, and R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

[0016] KR20190127529 A relates to an organic electroluminescent device, wherein at least one organic layer included in the organic electroluminescent device contains a boron-based organic compound of formula (1) and an anthracene-based organic compound of formula (2).

[0017]

[0018] US20200176679 A1 relates to a compound represented by Formula 1 as an organic compound having a narrow emission spectrum and a full width at half maximum and capable of suppressing concentration quenching phenomenon despite a high doping concentration.

[0019] in

[0020] Y is B, P(=O) or P(=S), and X1 and X2 are the same as or different from each other and are each independently selected from O, S, Se and N(R 12 ) group.

[0021] The compound of Formula 1 includes at least one or more substituted or unsubstituted cycloalkyl groups having 1 to 20 carbon atoms.

[0022] US2022093874 A1 relates to a light-emitting device and a polycyclic compound of formula 1 used therein

[0023]

[0024] in

[0025] W1 may be a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group, and Q1 may be NR16, O, or S. R1 to R16 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 ring carbon atoms, or the group shown in Formula 2 may be bonded to an adjacent group of R1 to R16.

[0026]

[0027] WO2021223688 A1 provides an organic compound of formula I and applications using the same as well as electronic components and electronic devices.

[0028]

[0029] in

[0030] At least one of R1, R2, R3, R4 and R5 is selected from

[0031]

[0032] The specific structure and substitution pattern of a compound can have a significant impact on the performance of that compound in organic electronic devices.

[0033] Despite the above developments, there is still a need for organic electroluminescent devices comprising new materials, in particular dopant (=emitter) materials, in order to provide improved properties of the electroluminescent devices.

[0034] Therefore, in view of the above-mentioned related art, it is an object of the present invention to provide materials suitable for providing organic electroluminescent devices, which ensure good performance of the organic electroluminescent devices, especially long lifetime and / or high efficiency. More particularly, it should be possible to provide dopant (=emitter) materials, especially blue light emitting dopant materials, having a narrow spectrum (small FWHM), i.e. good color purity when used as dopant in organic electroluminescent devices.

[0035] The object is solved according to one aspect of the present invention by a compound represented by formula (I):

[0036]

[0037] in

[0038] R 1 , R 2 , R 3 , R4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 20 , R 21 , R 22 , R 23 and R 24 Each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 30 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 30 ring atoms; unsubstituted or substituted aralkyl having 7 to 30 carbon atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted alkyl halide having 1 to 20 carbon atoms; unsubstituted or substituted alkenyl having 2 to 20 carbon atoms; unsubstituted or substituted alkynyl having 2 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; CN; NO2; OR 30 SR 31 ; C(=O)R 32 ;COOR 33 ;SiR 34 R 35 R 36 NR 84 R 85 or halogen;

[0039] or

[0040] Two adjacent residues together form an unsubstituted or substituted ring structure, preferably an unsubstituted or substituted alkyl ring;

[0041] in

[0042] R 1 , R 2 , R 3 and R 4 At least one, preferably R 2 and R 3 represents at least one of unsubstituted or substituted alkyl having 1 to 20 carbon atoms, or unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms, or two adjacent residues R 1 , R 2 , R 3 and R 4 , preferably R 2 and R 3 together form an unsubstituted or substituted alkyl ring;

[0043] R 5 , R 6 , R7 and R 8 At least one, preferably R 6 and R 7 represents at least one of unsubstituted or substituted alkyl having 1 to 20 carbon atoms, or unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms, or two adjacent residues R 5 , R 6 , R 7 and R 8 , preferably R 6 and R 7 together form an unsubstituted or substituted alkyl ring; and

[0044] R 21 , R 22 and R 23 At least one representative group HAr;

[0045] Y represents a group HAr or R Y ,in

[0046] R Y represents hydrogen; unsubstituted or substituted aryl having 6 to 30 ring carbon atoms; unsubstituted or substituted N-heteroaryl having 5 to 30 ring atoms; unsubstituted or substituted aralkyl having 7 to 30 carbon atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted alkyl halide having 1 to 20 carbon atoms; unsubstituted or substituted alkenyl having 2 to 20 carbon atoms; unsubstituted or substituted alkynyl having 2 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; CN; NO2; OR 30 SR 31 ; C(=O)R 32 ;COOR 33 ;SiR 34 R 35 R 36 NR 84 R 85 or halogen; or R Y Forming an unsubstituted or substituted ring with the adjacent residue at L; and

[0047] HAr represents a group of formula (II)

[0048]

[0049] in

[0050] R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R18 and R 19 Each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 30 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 30 ring atoms; unsubstituted or substituted aralkyl having 7 to 30 carbon atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted alkyl halide having 1 to 20 carbon atoms; unsubstituted or substituted alkenyl having 2 to 20 carbon atoms; unsubstituted or substituted alkynyl having 2 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; CN; NO2; OR 30 SR 31 ; C(=O)R 32 ;COOR 33 ;SiR 34 R 35 R 36 NR 84 R 85 or halogen;

[0051] or

[0052] Two adjacent residues together form an unsubstituted or substituted ring structure;

[0053] R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 One is the bonding site;

[0054] X is O, S or CR 25 R 26 ;

[0055] L represents an unsubstituted or substituted divalent aryl group having 6 to 30 ring carbon atoms; an unsubstituted or substituted divalent heteroaryl group having 5 to 30 ring atoms; an unsubstituted or substituted divalent alkyl group having 1 to 20 carbon atoms; or an unsubstituted or substituted divalent cycloalkyl group having 3 to 20 ring carbon atoms;

[0056] R 30 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36each independently represents an unsubstituted or substituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 30 ring atoms; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms;

[0057] R 25 , R 26 each independently represents an unsubstituted or substituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 30 ring atoms; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms;

[0058] or

[0059] R 25 and R 26 together to form an unsubstituted or substituted ring structure;

[0060] R 84 and R 85 each independently represents an unsubstituted or substituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 30 ring atoms; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms;

[0061] or

[0062] R 84 and R 85 together to form an unsubstituted or substituted ring structure;

[0063] n represents 0, 1, 2 or 3; preferably 0, 1 or 2; more preferably 0 or 1.

[0064] The compounds of formula (I) can in principle be used in any layer of an EL device. Preferably, the compounds of formula (I) are dopants (=emitters) in an organic EL element, especially in a light-emitting layer, more preferably fluorescent dopants. In particular, the compounds of formula (I) are used as fluorescent dopants in organic EL devices, especially in light-emitting layers.

[0065] The term organic EL device (organic electroluminescent device) is used interchangeably with the term organic light emitting diode (OLED) in this application.

[0066] It has been found that the specific compounds of formula (I) exhibit narrow emission characteristics, preferably narrow fluorescence, more preferably narrow blue fluorescence. Such narrow emission characteristics are suitable for preventing the energy loss caused by coupling out. The compounds of formula (I) according to the present invention preferably have a full width at half maximum (FWHM) lower than 30nm.

[0067] It has further been found that organic EL devices comprising the compounds of the present invention are generally characterized by high external quantum efficiency (EQE) and long lifetime, especially when the specific compounds of formula (I) are used as dopants (luminescent materials), especially fluorescent dopants, in organic electroluminescent devices.

[0068] Examples of optional substituents represented by "substituted or unsubstituted" and "possibly substituted" as mentioned above or below include aryl having 6 to 30, preferably 6 to 18 ring carbon atoms, which in turn is unsubstituted or substituted, heteroaryl having 5 to 30, preferably 5 to 18 ring atoms, which in turn is unsubstituted or substituted, alkyl having 1 to 20, preferably 1 to 8 carbon atoms, cycloalkyl having 3 to 20, preferably 3 to 6 carbon atoms, the group OR 30 , an alkyl halide group having 1 to 20, preferably 1 to 8, carbon atoms, an unsubstituted or substituted aralkyl group having 7 to 30 carbon atoms, a halogen atom (fluorine, chlorine, bromine, iodine), CN, C(═O)R 32 、COOR 33 , Silyl SiR 34 R 35 R 36 、Group SR 31 , NO2 and NR 84 R 85 ;

[0069] or

[0070] Two adjacent substituents together form a ring structure, which in turn is unsubstituted or substituted;

[0071] R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 84 and R 85 As defined above.

[0072] The terms hydrogen, halogen, unsubstituted or substituted alkyl having 1 to 20 carbon atoms, unsubstituted or substituted alkyl halide having 1 to 20 carbon atoms, unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30, preferably 6 to 18 ring carbon atoms; substituted or unsubstituted heteroaryl having 5 to 30, preferably 5 to 18 ring atoms, C(═O)R 32 , OR 30 , SR 31 、C(=O)R 32 、COOR 33 、SiR 34R 35 R 36 , unsubstituted or substituted aralkyl having 7 to 30 carbon atoms, unsubstituted or substituted alkenyl having 2 to 20 carbon atoms, and unsubstituted or substituted alkynyl having 2 to 20 carbon atoms and NR 84 R 85 are known in the art, and generally have the following meanings if the group is not further specified in the specific embodiments mentioned below.

[0073] In the present invention, hydrogen includes isotopes having different neutron numbers, namely, protium, deuterium and tritium.

[0074] The substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18, more preferably 6 to 13 ring carbon atoms may be a non-condensed aromatic group or a condensed aromatic group. Specific examples thereof include phenyl, naphthyl, phenanthrenyl, biphenyl, terphenyl, fluoranthenyl, triphenylene, phenanthrenyl, fluorenyl, indenyl, anthracenyl, phenyl, 1-naphthyl, 2-naphthyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, phenanthren-9-yl, phenanthren-3-yl, phenanthren-2-yl, triphenylene-2-yl, fluoren-2-yl, especially 9,9-di-C 1-20 Alkylfluoren-2-yl (such as 9,9-dimethylfluoren-2-yl), 9,9-di-C 6-18 Arylfluoren-2-yl (such as 9,9-diphenylfluoren-2-yl), or 9,9-di-C 5-18 Heteroarylfluoren-2-yl, fluoren-4-yl, especially 9,9-di-C 1-20 Alkylfluoren-4-yl (such as 9,9-dimethylfluoren-4-yl), 9,9-di-C 6-18 Arylfluoren-4-yl (such as 9,9-diphenylfluoren-4-yl), or 9,9-di-C 5-18 Heteroarylfluoren-4-yl, 1,1-dimethylindenyl, fluoranthen-3-yl, fluoranthen-2-yl and fluoranthen-8-yl are more preferred, and phenyl is most preferred.

[0075] The substituted or unsubstituted heteroaryl group having 5 to 30, preferably 5 to 18, more preferably 5 to 13 ring atoms may be a non-condensed heteroaromatic group or a condensed heteroaromatic group. Specific examples thereof include a pyrrole ring, an isoindole ring, a benzofuran ring, an isobenzofuran ring, a benzothiophene ring, a dibenzothiophene ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring, a phenanthridine ring, a phenanthroline ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, an indole ring, a quinoline ring, an acridine ring, a carbazole ring, a furan ring, a thiophene ring, a benzoxazole ring, a benzothiazole ring, a benzimidazole ring, a dibenzofuran ring, a triazine ring, an oxazole ring, an oxadiazole ring, a thiazole ring, a thiadiazole ring, a triazole ring, an imidazole ring, an indolidine ring, an imidazopyridine ring, 4-imidazo[1,2-a]benzimidazolyl, 5-benzimidazol[1,2-a] The residues of benzimidazolyl and benzimidazolo[2,1-b][1,3]benzothiazolyl, among which the residues of benzofuran ring, indole ring, benzothiophene ring, dibenzofuran ring, carbazole ring and dibenzothiophene ring are preferred, and the residues of benzofuran ring, 1-phenylindole ring, benzothiophene ring, dibenzofuran-1-yl, dibenzofuran-3-yl, dibenzofuran-2-yl, dibenzofuran-4-yl, 9-phenylcarbazole-3-yl, 9-phenylcarbazole-2-yl, 9-phenylcarbazole-4-yl, dibenzothiophene-2-yl and dibenzothiophene-4-yl, dibenzothiophene-1-yl and dibenzothiophene-3-yl are more preferred.

[0076] The substituted or unsubstituted N-heteroaryl group having 5 to 30, preferably 5 to 18, more preferably 5 to 13 ring atoms is as described above for the substituted or unsubstituted heteroaryl group, wherein at least one ring atom is nitrogen.

[0077] Examples of unsubstituted or substituted, straight or branched alkyl groups having 1 to 20 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, wherein methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl are preferred. Preferably, alkyl groups having 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms are preferred. Suitable examples of alkyl groups having 1 to 8 carbon atoms or 1 to 4 carbon atoms are mentioned above. Most preferably, methyl, isopropyl and tert-butyl are preferred. Preferably, the alkyl group is unsubstituted, ie it contains no atoms other than C and H, and no unsaturated groups or aromatic groups. However, the alkyl group may be straight-chain or branched.

[0078] Examples of unsubstituted or substituted alkyl halide groups having 1 to 20 carbon atoms include those disclosed as alkyl groups in which their hydrogen atoms are partially or completely substituted by halogen atoms. Preferred alkyl halide groups are fluoroalkyl groups having 1 to 20 carbon atoms including the alkyl groups mentioned above in which their hydrogen atoms are partially or completely substituted by fluorine atoms, such as CF3.

[0079] The example of the alkenyl with 2 to 20 carbon atoms that is unsubstituted or replaced comprises vinyl group, n-propylene group, isopropylene group, n-butylene group, isobutylene group, n-pentene group, n-hexene group, n-heptene group, n-octene group, n-nonene group, n-decene group, n-undecene group, n-dodecene group, n-tridecene group, n-tetradecene group, n-pentadecenyl group, n-hexadecene group, n-heptadecene group, n-octadecene group, n-octadecene group, wherein vinyl group, n-propylene group, isopropylene group, n-butylene group, isobutylene group are preferred.Preferably there is 2 to 8 carbon atoms, more preferably the alkenyl of 2 to 4 carbon atoms.The above mentioned suitable example of the alkenyl with 2 to 8 carbon atoms or 2 to 4 carbon atoms.

[0080] Examples of unsubstituted or substituted alkynyl groups having 2 to 20 carbon atoms include ethynyl, n-propynyl, n-butynyl, n-pentynyl, n-hexynyl, n-heptynyl, n-octynyl, of which ethynyl, n-propynyl, n-butynyl are preferred. Preferred are alkynyl groups having 2 to 8 carbon atoms, more preferably 2 to 4 carbon atoms. Suitable examples of alkynyl groups having 2 to 8 carbon atoms or 2 to 4 carbon atoms are mentioned above.

[0081] Examples of unsubstituted or substituted cycloalkyl groups having 3 to 20 ring carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and adamantyl, with cyclopentyl and cyclohexyl being preferred. Preferred are cycloalkyl groups having 3 to 6 carbon atoms. Suitable examples of cycloalkyl groups having 3 to 6 carbon atoms are mentioned above.

[0082] One example of the unsubstituted or substituted aralkyl group having 7 to 30 carbon atoms includes a benzyl group.

[0083] Examples of the halogen atom include fluorine, chlorine, bromine and iodine, among which fluorine is preferred.

[0084] Group OR 30 C is preferred 1-20 Alkoxy or C 6-18 Aryloxy. Examples of alkoxy groups having 1 to 20 carbon atoms, preferably 1 to 8 carbon atoms, include those having an alkyl moiety selected from the alkyl groups mentioned above. Examples of aryloxy groups having 6 to 18 ring carbon atoms include those having an aryl moiety selected from the aryl groups mentioned above, for example -OPh.

[0085] Group SR31 C is preferred 1-20 Alkylthio or C 6-18 Arylthio. Examples of alkylthio groups having 1 to 20 carbon atoms, preferably 1 to 8 carbon atoms, include those having an alkyl moiety selected from the alkyl groups mentioned above. Examples of arylthio groups having 6 to 18 ring carbon atoms include those having an aryl moiety selected from the aryl groups mentioned above, such as -SPh.

[0086] SiR 34 R 35 R 36 C is preferred 1-20 Alkyl and / or C 6-18 Aryl substituted silyl. 1-20 Alkyl and / or C 6-18 Preferred examples of aryl-substituted silyl groups include alkylsilyl groups having 1 to 8 carbon atoms, preferably 1 to 4 carbon atoms, in each alkyl residue, including trimethylsilyl, triethylsilyl, tributylsilyl, dimethylethylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, dimethylisopropylsilyl, dimethylpropylsilyl, dimethylbutylsilyl, dimethyltert-butylsilyl, diethylisopropylsilyl, and arylsilyl groups having 6 to 18 ring carbon atoms in each aryl residue, preferably triphenylsilyl, and alkyl / arylsilyl groups, preferably phenyldimethylsilyl, diphenylmethylsilyl and diphenyltert-butylsilyl, of which diphenyltert-butylsilyl and tert-butyldimethylsilyl are preferred.

[0087] Group NR 84 R 85 is an amino group, where R 84 and R 85 As described above. Preferably, R 84 and R 85 Each independently represents an unsubstituted or substituted aryl group having 6 to 30 ring carbon atoms; or an unsubstituted or substituted heteroaryl group having 5 to 30 ring atoms. Preferably, R 84 and R 85 Each independently represents an unsubstituted or substituted aryl group having 6 to 18 ring carbon atoms; or an unsubstituted or substituted heteroaryl group having 5 to 18 ring atoms.

[0088] The optional substituents preferably each independently represent unsubstituted or substituted aryl having 6 to 18 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 18 ring atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; halogen, CN; SiR 34 R 35R 36 , SR 31 OR 30 ;

[0089] or

[0090] Two adjacent substituents together form a ring structure, which in turn is unsubstituted or substituted.

[0091] More preferably, the optional substituents each independently represent an unsubstituted or substituted aryl group having 6 to 18 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 18 ring atoms; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms; an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms; a halogen, SiR 34 R 35 R 36 or CN;

[0092] or

[0093] Two adjacent substituents together form a ring structure, which in turn is unsubstituted or substituted.

[0094] Most preferably, the optional substituents each independently represent an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms; an unsubstituted or substituted cycloalkyl group having 3 to 6 ring carbon atoms; an unsubstituted or substituted aryl group having 6 to 13 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 13 ring atoms; a halogen, SiR 34 R 35 R 36 or CN.

[0095] R 30 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 Each independently represents an unsubstituted or substituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 30 ring atoms; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms.

[0096] The above-mentioned optional substituents may be further substituted with one or more of the above-mentioned optional substituents.

[0097] The number of optional substituents depends on the group substituted by the substituents. The maximum number of possible substituents is limited by the number of hydrogen atoms present.

[0098] According to the present invention,

[0099] R1 , R 2 , R 3 and R 4 At least one, preferably R 2 and R 3 At least one of represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms;

[0100] R 5 , R 6 , R 7 and R 8 At least one, preferably R 6 and R 7 At least one of represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms; and

[0101] R 21 , R 22 and R 23 At least one of represents the group HAr.

[0102] The compounds of formula (I) must therefore contain at least 3 substituents, namely R 1 , R 2 , R 3 and R 4 At least one of the first substituents, R 5 , R 6 , R 7 and R 8 as a second substituent, and R 21 , R 22 and R 23 as the third substituent.

[0103] Preferably, the total number of substituents in the compounds of formula (I) is 3, 4, 5, 6, 7 or 8, preferably 3, 4, 5 or 6, ie the remaining residues are hydrogen.

[0104] The "carbon number of a to b" in the expression "a substituted or unsubstituted X group having a to b carbon atoms" is the carbon number of the unsubstituted X group and does not include carbon atoms of the optional substituent.

[0105] The term "unsubstituted" referred to by "unsubstituted or substituted" means that a hydrogen atom is not replaced by one of the substituents mentioned above.

[0106] The index 0 in the definitions in the formulae mentioned above and below means that a hydrogen atom is present at the position defined by said index.

[0107] An example of a ring structure formed by two adjacent substituents is shown below:

[0108] For example

[0109]

[0110] For example

[0111] For example

[0112] For example

[0113] For example like

[0114]

[0115] For example

[0116] For example

[0117] For example

[0118] in

[0119] X' represents O, S or CR 68 R 69 ;

[0120] R 42 , R 43 , R 44 , R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 , R 54 , R 55 , R 56 , R 57 , R 58 , R 59 , R 60 , R 61 , R 62 , R 63 , R 64 , R 65 , R 66 and R 67, R 70 , R 71 , R 72 , R 73 , R 74 , R 75 , R 76 , R 77 and R 78 Each independently represents hydrogen, unsubstituted or substituted aryl having 6 to 60 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 60 ring atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms;

[0121] or

[0122] Two adjacent residues together form an unsubstituted or substituted ring structure,

[0123] The dashed lines are bonding sites;

[0124] R 68 and R 69 each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 60 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 60 ring atoms or unsubstituted or substituted alkyl having 1 to 20 carbon atoms;

[0125] or

[0126] R 68 and R 69 together form an unsubstituted or substituted aromatic ring structure having 3 to 13 ring atoms or an unsubstituted or substituted aliphatic ring structure having 3 to 9 ring atoms;

[0127] X" and Y" independently represent O, CR c R d , S, BR e or NR e ,

[0128] R c and R d Each independently represents a C1 to C8 alkyl group or a substituted or unsubstituted C6 to C 18 Aryl, preferably C1 to C4 alkyl or substituted or unsubstituted C6 to C 10 Aryl, more preferably methyl or unsubstituted or substituted phenyl,

[0129] R e represents a C1 to C8 alkyl group, preferably a C1 to C4 alkyl group, or a substituted or unsubstituted C6 to C 10 Aryl, preferably unsubstituted or substituted phenyl,

[0130] and

[0131] Dashed lines are bonding sites.

[0132] Preferred examples of the ring structure formed by two adjacent substituents are the ring structures (A), (D), (G) and (H), and a more preferred ring structure formed by two adjacent substituents is

[0133]

[0134] Compounds of formula (I)

[0135] In the compound of formula (I):

[0136] -R 1 , R 2 , R 3 and R 4 At least one, preferably R 2 and R 3 represents at least one of unsubstituted or substituted alkyl having 1 to 20 carbon atoms, or unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms, or two adjacent residues R 1 , R 2 , R 3 and R 4 , preferably R 2 and R 3 Together they form an unsubstituted or substituted alkyl ring.

[0137] -R 5 , R 6 , R 7 and R 8 At least one, preferably R 6 and R 7 represents at least one of unsubstituted or substituted alkyl having 1 to 20 carbon atoms, or unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms, or two adjacent residues R 5 , R 6 , R 7 and R 8 , preferably R 6 and R 7 Together they form an unsubstituted or substituted alkyl ring.

[0138] -R 21 , R 22 and R 23 At least one of represents the group HAr.

[0139] R 1 , R 2 , R 3 and R 4 At least one, preferably R 2 and R 3 At least one of R 5 , R6 , R 7 and R 8 At least one, preferably R 6 and R 7 At least one of the residues independently represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms, or two adjacent residues together form an unsubstituted or substituted alkyl ring.

[0140] Suitable and preferred unsubstituted or substituted alkyl groups having 1 to 20 carbon atoms and unsubstituted or substituted cycloalkyl groups having 3 to 20 ring carbon atoms are mentioned above. 1 , R 2 , R 3 and R 4 At least one, preferably R 2 and R 3 At least one of R 5 , R 6 , R 7 and R 8 At least one, preferably R 6 and R 7 At least one of them, each independently represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, more preferably an unsubstituted or substituted alkyl group having 1 to 8 carbon atoms, most preferably an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms, further most preferably a methyl group or a tert-butyl group.

[0141] It is further preferred that the above-mentioned alkyl group is unsubstituted. However, it is linear or branched.

[0142] Suitable and preferred unsubstituted or substituted alkyl rings are mentioned above. Preferably, two adjacent residues R 1 , R 2 , R 3 and R 4 , preferably R 2 and R 3 , and / or R 5 , R 6 , R 7 and R 8 , preferably R 6 and R 7 Together they form the above-mentioned ring structure (G) or (H). More preferably one of the following ring structures:

[0143]

[0144] Preferably,

[0145] R 1 , R 2 , R3 and R 4 Exactly one, preferably R 2 and R 3 of exactly one, and R 5 , R 6 , R 7 and R 8 Exactly one, preferably R 6 and R 7 Exactly one of each independently represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms. Preferred alkyl and cycloalkyl groups are mentioned above;

[0146] or

[0147] Two adjacent residues R 1 , R 2 , R 3 and R 4 , preferably R 2 and R 3 together form an unsubstituted or substituted alkyl ring, and / or two adjacent residues R 5 , R 6 , R 7 and R 8 , preferably R 6 and R 7 Together they form an unsubstituted or substituted alkyl ring, wherein the preferred alkyl ring forms a ring structure (G) or (H) as mentioned above, preferably

[0148] R 21 , R 22 and R 23 At least one representative group HAr

[0149] The group HAr is a group of formula (II)

[0150]

[0151] R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19Each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 30 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 30 ring atoms; unsubstituted or substituted aralkyl having 7 to 30 carbon atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted alkyl halide having 1 to 20 carbon atoms; unsubstituted or substituted alkenyl having 2 to 20 carbon atoms; unsubstituted or substituted alkynyl having 2 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; CN; NO2; OR 30 SR 31 ; C(=O)R 32 ;COOR 33 ;SiR 34 R 35 R 36 NR 84 R 85 or halogen;

[0152] or

[0153] Two adjacent residues together form an unsubstituted or substituted ring structure;

[0154] R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 One is the bonding site.

[0155] X is O, S or CR 25 R 26 .

[0156] Preferably, R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 30 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 30 ring atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; or halogen;

[0157] or

[0158] Two adjacent residues together form an unsubstituted or substituted ring structure, wherein suitable and preferred ring structures are mentioned above;

[0159] R12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 One is the bonding site.

[0160] More preferably, R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 Each independently represents hydrogen; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms; or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms;

[0161] or

[0162] Two adjacent residues together form an unsubstituted or substituted ring structure, wherein suitable and preferred ring structures are mentioned above;

[0163] R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 One is the bonding site.

[0164] Most preferably, R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 Each independently represents hydrogen; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms; or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms;

[0165] R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 One is the bonding site.

[0166] More preferably, R 12 , R 13 , R14 , R 15 , R 16 , R 17 , R 18 and R 19 0, 1 or 2 of each independently represent hydrogen; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; or unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms, and the remaining residues are H;

[0167] R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 One is the bonding site.

[0168] Examples of suitable groups of formula (II) are:

[0169]

[0170] in

[0171] R 14 , R 17 , R 18 , R 19 , R 25 and R 26 As mentioned above, and

[0172] Dashed lines are bonding sites.

[0173] In a preferred embodiment, R 21 , R 22 and R 23 Exactly one, preferably R 22 In a further preferred embodiment, R 21 represents the group HAr. Preferred groups HAr are mentioned above.

[0174] Preferably, R 25 , R 26 Each independently represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, preferably an unsubstituted alkyl group having 1 to 8 carbon atoms, more preferably an unsubstituted alkyl group having 1 to 4 carbon atoms, and most preferably a methyl group;

[0175] or

[0176] R 25 and R 26 Together they form an unsubstituted or substituted ring structure.

[0177] In one embodiment, R25 and R 26 Do not form together an unsubstituted or substituted ring structure.

[0178] More preferably, R 25 , R 26 Each independently represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, preferably an unsubstituted alkyl group having 1 to 8 carbon atoms, more preferably an unsubstituted alkyl group having 1 to 4 carbon atoms, and most preferably a methyl group; or an unsubstituted or substituted aryl group having 6 to 30 ring carbon atoms, preferably 6 to 18 ring carbon atoms, more preferably 6 to 13 ring carbon atoms, most preferably an unsubstituted or substituted phenyl group, and further most preferably an unsubstituted phenyl group.

[0179] The remaining groups R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 20 , R 21 , R 22 , R 23 and R 24

[0180] The remaining groups R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 20 , R 21 , R 22 , R 23 and R 24 , i.e. the groups which are not compulsorily defined as unsubstituted or substituted alkyl having 1 to 20 carbon atoms and unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms, two adjacent residues together forming an unsubstituted or substituted alkyl ring, and the groups defined as the group HAr each independently represent hydrogen;

[0181] Each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 30 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 30 ring atoms; unsubstituted or substituted aralkyl having 7 to 30 carbon atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted alkyl halide having 1 to 20 carbon atoms; unsubstituted or substituted alkenyl having 2 to 20 carbon atoms; unsubstituted or substituted alkynyl having 2 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; CN; NO2; OR 30 SR 31 ; C(=O)R 32 ;COOR 33 ;SiR 34 R 35 R 36 NR 84 R 85 or halogen;

[0182] or

[0183] Two adjacent residues together form an unsubstituted or substituted ring structure, preferably an unsubstituted or substituted alkyl ring;

[0184] Preferably, the remaining groups R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 20 , R 21 , R 22 , R 23 and R 24 Each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 30 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 30 ring atoms; unsubstituted or substituted aralkyl having 7 to 30 carbon atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted alkyl halide having 1 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; or NR 84 R 85 ;

[0185] or

[0186] Two adjacent residues together form an unsubstituted or substituted ring structure, preferably an unsubstituted or substituted alkyl ring.

[0187] More preferably, the remaining groups R1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 20 , R 21 , R 22 , R 23 and R 24 Each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 30 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 30 ring atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; or NR 84 R 85 ;

[0188] or

[0189] Two adjacent residues together form an unsubstituted or substituted ring structure, preferably an unsubstituted or substituted alkyl ring.

[0190] More preferably, the remaining groups R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 20 , R 21 , R 22 , R 23 and R 24 Each independently represents hydrogen;

[0191] and

[0192] R 9 , R 10 and R 11 At least one, preferably R 10 represents hydrogen, unsubstituted or substituted alkyl having 1 to 20 carbon atoms, or unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted or substituted aryl having 6 to 30 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 30 ring atoms; NR 84 R 85 ,or

[0193] R 9 and R 10 , and / or R10 and R 11 Together they form an unsubstituted or substituted ring structure, preferably an unsubstituted or substituted alkyl ring. Suitable ring structures are mentioned above.

[0194] In a further embodiment, R 1 , R 4 , R 5 , R 8 , R 9 , R 11 , R 20 and R 24 is hydrogen; or

[0195] R 1 , R 4 , R 5 , R 8 , R 9 and R 11 is hydrogen, and

[0196] R 20 and R 24 Each independently represents hydrogen or an unsubstituted or substituted aryl group having 6 to 30 ring carbon atoms, preferably 6 to 18 ring carbon atoms, more preferably 6 to 13 ring carbon atoms, most preferably unsubstituted or substituted phenyl, further most preferably unsubstituted phenyl.

[0197] L, n, Y

[0198] L represents an unsubstituted or substituted divalent aryl group having 6 to 30 ring carbon atoms; an unsubstituted or substituted divalent heteroaryl group having 5 to 30 ring atoms; an unsubstituted or substituted divalent alkyl group having 1 to 20 carbon atoms; or an unsubstituted or substituted divalent cycloalkyl group having 3 to 20 ring carbon atoms;

[0199] Preferably, L represents an unsubstituted or substituted divalent aromatic group having 6 to 30 ring carbon atoms; or an unsubstituted or substituted divalent heteroaromatic group having 5 to 30 ring atoms;

[0200] More preferably, L represents an unsubstituted or substituted divalent aryl group having 6 to 24 ring carbon atoms, preferably 6 to 18 ring atoms, or an unsubstituted or substituted divalent heteroaryl group having 5 to 24 ring atoms, preferably 5 to 18 ring atoms;

[0201] Still more preferably, L represents an unsubstituted or substituted phenylene group, an unsubstituted or substituted divalent naphthyl group, an unsubstituted or substituted divalent anthracenyl group, an unsubstituted or substituted divalent phenanthryl group, an unsubstituted or substituted divalent triphenylene group, an unsubstituted or substituted divalent 9,9-dimethylfluorenyl group, an unsubstituted or substituted divalent 9,9-diphenylfluorenyl group or an unsubstituted or substituted divalent heteroaryl group having 3 to 24 ring atoms, preferably 3 to 14 ring atoms;

[0202] Most preferably, L represents unsubstituted or substituted phenylene, for example 1,2-phenylene, 1,3-phenylene or 1,4-phenylene.

[0203] N represents 0, 1, 2 or 3; preferably 0, 1 or 2; more preferably 0 or 1. In the case where n represents 0, there is a direct bond between N and Y.

[0204] When n is 1, L is preferably a group of the formula:

[0205]

[0206] in

[0207] R 37 , R 38 , R 39 , R 40 and R 41

[0208] Each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 30 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 30 ring atoms; unsubstituted or substituted aralkyl having 7 to 30 carbon atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted alkyl halide having 1 to 20 carbon atoms; unsubstituted or substituted alkenyl having 2 to 20 carbon atoms; unsubstituted or substituted alkynyl having 2 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; CN; NO2; OR 30 SR 31 ; C(=O)R 32 ;COOR 33 ;SiR 34 R 35 R 36 NR 84 R 85 or halogen;

[0209] or

[0210] Two adjacent residues together form an unsubstituted or substituted ring structure, preferably an unsubstituted or substituted alkyl ring or an unsubstituted or substituted aryl ring, such as naphthyl or anthracenyl;

[0211] in

[0212] R 37 , R 38 , R 39 , R 40 and R 41 One, preferably R 39 or R 40 , more preferably R39 It is Y;

[0213] And the dashed lines are the bonding sites.

[0214] Y is a group HAr or R Y .

[0215] The group HAr is a group of formula (II) as defined above.

[0216] R Y represents hydrogen; unsubstituted or substituted aryl having 6 to 30 ring carbon atoms; unsubstituted or substituted N-heteroaryl having 5 to 30 ring atoms; unsubstituted or substituted aralkyl having 7 to 30 carbon atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted alkyl halide having 1 to 20 carbon atoms; unsubstituted or substituted alkenyl having 2 to 20 carbon atoms; unsubstituted or substituted alkynyl having 2 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; CN; NO2; OR 30 SR 31 ; C(=O)R 32 ;COOR 33 ;SiR 34 R 35 R 36 NR 84 R 85 or halogen; or R Y It forms an unsubstituted or substituted ring with the adjacent residue at L.

[0217] The neighboring residue at L is preferably a residue R other than Y. 37 , R 38 , R 39 , R 40 and R 41 one.

[0218] Preferably, R Y represents hydrogen; unsubstituted or substituted aryl having 6 to 30 ring carbon atoms; unsubstituted or substituted N-heteroaryl having 5 to 30 ring atoms; unsubstituted or substituted aralkyl having 7 to 30 carbon atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; or unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; or R Y The adjacent residue at L, preferably a residue R other than Y 37 , R 38 , R 39 , R 40 and R 41 One of them forms an unsubstituted or substituted alkyl ring.

[0219] More preferably, RY represents hydrogen, unsubstituted or substituted alkyl having 1 to 20 carbon atoms, more preferably unsubstituted or substituted alkyl having 1 to 8 carbon atoms, most preferably unsubstituted or substituted alkyl having 1 to 4 carbon atoms, further most preferably methyl or tert-butyl; further preferably, the above-mentioned alkyl is unsubstituted, however, it is linear or branched; or R Y The adjacent residue at L, preferably a residue R other than Y 37 , R 38 , R 39 , R 40 and R 41 One of them forms an unsubstituted or substituted alkyl ring; or R Y represents an unsubstituted or substituted aryl group having 6 to 30 ring carbon atoms, preferably 6 to 18 ring carbon atoms, more preferably 6 to 13 ring carbon atoms, most preferably unsubstituted or substituted phenyl, further most preferably unsubstituted phenyl.

[0220] Suitable and preferred unsubstituted or substituted alkyl rings are mentioned above; more preferred alkyl rings are represented by the ring structures (G) or (H) mentioned above, and the most preferred alkyl rings are:

[0221]

[0222] Preferably,

[0223] R 37 , R 38 , R 39 , R 40 and R 41 One, preferably R 39 and R 40 One of the above, more preferably R 39 Represents R Y ;

[0224] or

[0225] Two adjacent residues R Y and R that is not Y 37 , R 38 , R 39 , R 40 and R 41 One, preferably in R 39 and R 40 The position of R Y Together they form an unsubstituted or substituted alkyl ring, wherein the preferred alkyl ring forms a ring structure (G) or (H) as mentioned above, preferably

[0226] and

[0227] R37 , R 38 , R 39 , R 40 and R 41 The remaining residues are hydrogen.

[0228] Preferably, when Y is HAr, R 37 , R 38 , R 39 , R 40 and R 41 One, preferably R 39 or R 40 , more preferably R 39 is HAr, wherein suitable and preferred groups HAr are the same groups HAr as mentioned above.

[0229] In the case where n is 2 or 3, the groups L may be the same or different. In this case, the group -(L) n - In the case of n=2, it can be described as -L1-L2- and in the case of n=3, it can be described as -L1-L2-L3-.

[0230] In this case (n=2 or 3), L1 is the radical farthest from N, and L2 (in the case of n=2) or L3 (in the case of n=3) is the radical closest to N, respectively.

[0231] L1, L2 and L3 are defined in the same manner as L.

[0232] L1 is preferably defined as mentioned above for L in the case of n=1.

[0233] L2 and L3 are each independently preferably an unsubstituted or substituted phenyl group, more preferably an unsubstituted or substituted 1,2-phenylene, 1,3-phenylene or 1,4-phenylene group, most preferably an unsubstituted 1,2-phenylene, 1,3-phenylene or 1,4-phenylene group, and further most preferably an unsubstituted 1,3-phenylene or 1,4-phenylene group.

[0234] Group Y–(L) n An example of - is

[0235]

[0236]

[0237] The residue and group R Y , R 13 and X are as described above and below. Preferred groups Y—(L) n -yes:

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244] More preferred groups Y-(L) n -yes:

[0245]

[0246]

[0247]

[0248]

[0249] Preferred compounds of formula (I) are shown below, wherein the residues and groups and indices are as defined above

[0250]

[0251] More preferred compounds of formula (I) are those wherein the residues, groups and indices are as defined above

[0252]

[0253]

[0254] More preferably, in the compounds of formula (Ia), (Ib), (Iaa), (Iba), (Iab) and (Ibb):

[0255] R 1 , R 4 , R 5 , R 8 , R 9 , R 11 , R 20 and R 24 is hydrogen; or R 1 , R 4 , R 5 , R 8 , R 9 and R 11 is hydrogen, and R 20 and R 24each independently represents hydrogen or an aryl group having 6 to 30 ring carbon atoms;

[0256] R 2 and R 3 At least one of the residues R represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms, and the remaining residues R 2 or R 3 is hydrogen; or

[0257] R 2 and R 3 together form an unsubstituted or substituted alkyl ring;

[0258] R 6 and R 7 At least one of the residues R represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms, and the remaining residues R 6 or R 7 is hydrogen; or

[0259] R 6 and R 7 together form an unsubstituted or substituted alkyl ring;

[0260] R 10 represents hydrogen, unsubstituted or substituted alkyl having 1 to 20 carbon atoms, unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms or NR 84 R 85 ; or an aryl group having 6 to 30 ring carbon atoms;

[0261] R Y represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms, or R Y Together with the adjacent residue at L, it forms an unsubstituted or substituted alkyl ring; or R Y represents hydrogen or an aryl group having 6 to 30 ring carbon atoms;

[0262] R 84 and R 85 Each independently represents an unsubstituted or substituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 30 ring atoms;

[0263] L represents an unsubstituted or substituted phenylene group; and

[0264] n is 0 or 1.

[0265] Examples of compounds of formula (I) are given below:

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300] Preparation of compounds of formula (I)

[0301] The compounds represented by formula (I) can be synthesized according to the reactions performed in the examples of the present application and by reactions and starting materials similar to those known in the art, using alternative reactions or starting materials suitable for the desired product.

[0302] The compound of formula (I) is prepared, for example, by the following steps:

[0303] (i) adding A-Li to the intermediate (III) to generate lithiated species in situ;

[0304] (ii) adding BHal'3 to the lithiated intermediate (III), or adding BOR*3 to the lithiated intermediate (III), thereby obtaining the intermediate (IV):

[0305]

[0306] in

[0307] A represents a linear or branched, substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms. Preferably, A represents a linear or branched, unsubstituted alkyl group having 1 to 6 carbon atoms;

[0308] Hal represents halogen, preferably F, Cl, Br or I, more preferably Cl or Br, most preferably Br;

[0309] Hal' represents halogen, preferably F, Cl, Br or I, more preferably Cl or Br, most preferably Br;

[0310] R in intermediate (IV) 20 , R 21, R 22 , R 23 and R 24 One of them is Hal”;

[0311] Hal" represents halogen, preferably F, Cl, Br or I, more preferably Cl or Br, most preferably Cl;

[0312] R* represents an unsubstituted alkyl group having 1 to 8 carbon atoms, an unsubstituted cycloalkyl group having 3 to 6 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms substituted by one or two unsubstituted alkyl groups having 1 to 8 carbon atoms, or an unsubstituted alkoxy group having 1 to 8 carbon atoms;

[0313] or two residues R* are linked together to form a ring, e.g.

[0314] All other residues, groups and indices are as defined above;

[0315] An example of a preferred intermediate (IV) is intermediate (IVa) wherein R 22 It's Hal':

[0316]

[0317] (i) The halogen atom of the intermediate (IV) reacts with BQ2-HAr (V) to obtain a compound of formula (I)

[0318]

[0319] in

[0320] R in BQ2-HAr(V) 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 One is -BQ2;

[0321] Q is an unsubstituted alkyl group having 1 to 8 carbon atoms, an unsubstituted cycloalkyl group having 3 to 6 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms substituted by one or two unsubstituted alkyl groups having 1 to 8 carbon atoms, an unsubstituted alkoxy group having 1 to 8 carbon atoms, or a hydroxyl group, wherein two alkyl groups Q or two alkoxy groups Q together form a 5- or 6-membered substituted or unsubstituted ring;

[0322] Catalyst: Preferably the catalyst is a Pd catalyst;

[0323] All other residues, groups and indices are as defined above.

[0324] Usually, the intermediate (IV) can also be 20 , R 21 , R 22 , R 23 and R 24 One of them is to prepare a compound of formula (I) by reacting a compound of formula (IV) wherein -BQ2 with a compound of formula

[0325]

[0326] Among them, R in BQ2-HAr(V) 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 One of them is Hal."

[0327] An example of a preferred intermediate BQ2-HAr(V) is intermediate (Va) wherein R 14 Yes – BQ2:

[0328]

[0329] Suitable Pd catalysts are, for example, Pd(0) complexes with bidentate ligands such as dba (dibenzylideneacetone), or in combination with bidentate phosphine ligands such as dppf ((diphenylphosphino)ferrocene), dppp ((diphenylphosphino)propane), BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl), Xantphos (4,5-bis(diphenylphosphino)-9,9-dimethylxanthene), DPEphos (bis[(2-diphenylphosphino)phenyl]ether) or Josiphos, or Pd(II) salts such as PdCl2 or Pd(OAc)2 in combination with a monodentate phosphine ligand such as triphenylphosphine, tri-o-tolylphosphine, tri-tert-butylphosphine, tricyclohexylphosphine, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos) or N-heterocyclic carbenes such as 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IPr), 1,3-dimesityl imidazol-2-ylidene (Imes).

[0330] Josiphos:

[0331] wherein R and R' are typically substituted or unsubstituted phenyl.

[0332] The order of steps (i) and (ii) in the above method can generally be changed, that is, the addition of BQ2-HAr is performed first (equivalent to step (ii)), followed by borylation of the resulting intermediate (equivalent to step (i)).

[0333] Suitable reaction conditions are known to the person skilled in the art.The reaction steps for obtaining intermediates (III), (IV) and (V) are shown in the examples of the present application.

[0334] Details of all reaction steps and process conditions are mentioned in the examples of this application.

[0335] Organic electroluminescent devices

[0336] According to one aspect of the present invention, there is provided a material for an organic electroluminescent device, comprising at least one compound of formula (I).

[0337] According to another aspect of the present invention, there is provided an organic electroluminescent device comprising at least one compound of formula (I).

[0338] According to another aspect of the present invention, the following organic electroluminescent device is provided: an organic electroluminescent device comprising a cathode, an anode and one or more organic thin film layers containing a light emitting layer arranged between the cathode and the anode, wherein at least one layer of the organic thin film layer comprises at least one compound of formula (I).

[0339] According to another aspect of the present invention, there is provided an organic electroluminescent device, wherein the light emitting layer comprises at least one compound of formula (I).

[0340] According to another aspect of the present invention, there is provided an organic electroluminescent device, wherein the light emitting layer comprises at least one compound of formula (I) as a dopant material and an anthracene compound as a host material.

[0341] According to another aspect of the present invention, there is provided an electronic device having the organic electroluminescent device according to the present invention.

[0342] According to another aspect of the present invention, there is provided an emitter material comprising at least one compound of formula (I).

[0343] According to another aspect of the present invention, there is provided a light emitting layer comprising at least one host and at least one dopant, wherein the dopant comprises at least one compound of formula (I).

[0344] According to another aspect of the present invention, there is provided use of the compound of formula (I) according to the present invention in an organic electroluminescent device.

[0345] In one embodiment, the organic EL device comprises a hole transport layer between the anode and the emissive layer.

[0346] In one embodiment, the organic EL device comprises an electron transport layer between the cathode and the emissive layer.

[0347] In this specification, with respect to "one or more organic thin film layers between the emission layer and the anode", if there is only one organic layer between the emission layer and the anode, it refers to that layer, and if there are multiple organic layers, it refers to at least one layer thereof. For example, if there are two or more organic layers between the emission layer and the anode, the organic layer closer to the emission layer is referred to as the "hole transport layer", and the organic layer closer to the anode is referred to as the "hole injection layer". The "hole transport layer" and the "hole injection layer" can each be a single layer or can be formed by two or more layers. One of these layers can be a single layer, and the other can be formed by two or more layers.

[0348] Similarly, with respect to “one or more organic thin film layers between the emission layer and the cathode”, if there is only one organic layer between the emission layer and the cathode, it refers to that layer, and if there are multiple organic layers, it refers to at least one layer thereof. For example, if there are two or more organic layers between the emission layer and the cathode, the organic layer closer to the emission layer is referred to as the “electron transport layer”, and the organic layer closer to the cathode is referred to as the “electron injection layer”. The “electron transport layer” and the “electron injection layer” can each be a single layer or can be formed of two or more layers. One of these layers can be a single layer, and the other can be formed of two or more layers.

[0349] The "one or more organic thin film layers comprising an emission layer" mentioned above, preferably an emission layer, comprises a compound represented by formula (I). The compound represented by formula (I) preferably acts as an emitter material, more preferably acts as a fluorescent emitter material, and most preferably acts as a blue fluorescent emitter material. The compound of formula (I) is present in an organic EL device, preferably in an emission layer, to provide an organic EL device characterized by high external quantum efficiency (EQE) and long life.

[0350] According to another aspect of the present invention, there is provided an emission layer of an organic electroluminescent device, comprising at least one compound of formula (I).

[0351] Preferably, the emissive layer comprises at least one emissive material (dopant material) and at least one host material, wherein the emissive material is at least one compound of formula (I).

[0352] In one embodiment, the host is not selected from CBP (4,4'-bis-(N-carbazolyl)-biphenyl), mCP, mCBPSif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), CzSi, Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenyl]ether oxide), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, azole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine) and / or TST (2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine).

[0353] Preferred host materials are substituted or unsubstituted polycyclic aromatic hydrocarbon (PAH) compounds, substituted or unsubstituted polycyclic heteroaromatic compounds, substituted or unsubstituted anthracene compounds, or substituted or unsubstituted pyrene compounds.

[0354] More preferably, the organic electroluminescent device according to the present invention comprises at least one compound of formula (I) as a dopant material and at least one host material selected from the group consisting of substituted or unsubstituted polycyclic aromatic hydrocarbon (PAH) compounds, substituted or unsubstituted polycyclic heteroaromatic compounds, substituted or unsubstituted anthracene compounds and substituted or unsubstituted pyrene compounds in the emission layer. Preferably, the at least one host is at least one substituted or unsubstituted anthracene compound.

[0355] In a further preferred embodiment, the organic electroluminescent device according to the present invention comprises at least one compound of formula (I) as a dopant material and at least one host material selected from the group consisting of substituted or unsubstituted polycyclic aromatic hydrocarbon (PAH) compounds, substituted or unsubstituted anthracene compounds and substituted or unsubstituted pyrene compounds in the emission layer. Preferably, the at least one host is at least one substituted or unsubstituted anthracene compound.

[0356] According to another aspect of the present invention, there is provided an emission layer of an organic electroluminescent device, comprising at least one compound of formula (I) as a dopant material and an anthracene compound as a host material.

[0357] Suitable anthracene compounds are represented by the following formula (10):

[0358]

[0359] in

[0360] Two or more adjacent R 101 To R 110 One or more pairs of may form a substituted or unsubstituted, saturated or unsaturated ring;

[0361] R does not form a substituted or unsubstituted, saturated or unsaturated ring 101 To R 110 independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms, a substituted or unsubstituted alkylene group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms, -Si(R 121 )(R 122 )(R 123 ), -C(=O)R 124 、-COOR 125 、-N(R 126 )(R 127 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or a group represented by the following formula (31);

[0362] R 121 To R 127 are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; when R 121 To R 127 When multiple R 121 To R 127 Each can be the same or different;

[0363] Provided that there is no R forming a substituted or unsubstituted, saturated or unsaturated ring 101 To R 110 At least one of the groups is a group represented by the following formula (31). If there are two or more groups represented by the formula (31), these groups may be the same or different;

[0364] -L 101 -Ar101 (31)

[0365] In formula (31),

[0366] L 101 is a single bond, a substituted or unsubstituted arylene group containing 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group containing 5 to 30 ring atoms;

[0367] Ar 101 is a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group comprising 5 to 50 ring atoms.

[0368] Specific examples of each substituent in the compound (10), the substituent related to "substituted or unsubstituted", and the halogen atom are the same as those mentioned above.

[0369] Two or more adjacent R 101 To R 110 One or more pairs of them may form a substituted or unsubstituted, saturated or unsaturated ring”.

[0370] "Two or more adjacent R 101 To R 110 A pair of "is for example R 101 and R 102 , R 102 and R 103 , R 103 and R 104 , R 105 and R 106 , R 106 and R 107 , R 107 and R 108 , R 108 and R 109 , R 101 and R 102 and R 103 And so on.

[0371] The substituent in "substituted" in "substituted or unsubstituted" with respect to the saturated or unsaturated ring is the same as the substituent in "substituted or unsubstituted" mentioned in formula (10).

[0372] When R 101 and R 102 When forming a ring, a "saturated or unsaturated ring" refers to, for example, a ring consisting of 101 The carbon atom bonded to R 102 A ring formed by bonding carbon atoms and one or more arbitrary elements. Specifically, when the ring is composed of R 101 and R 102 When the unsaturated ring is formed by101 The carbon atom bonded to R 102 When the bonded carbon atom is formed with four carbon atoms, R 101 and R 102 The ring formed is a benzene ring.

[0373] The "arbitrary element" is preferably a C element, a N element, an O element or an S element. In the arbitrary element (for example, a C element or a N element), atomic bonds that do not form a ring may be terminated with a hydrogen atom or the like.

[0374] The “one or more arbitrary elements” are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less arbitrary elements.

[0375] For example, R 101 and R 102 can form a ring, and at the same time, R 105 and R 106 In this case, the compound represented by formula (10) is, for example, a compound represented by the following formula (10A):

[0376]

[0377] In one embodiment, R 101 To R 110 It is independently a hydrogen atom, a substituted or unsubstituted alkyl group containing 1 to 50 carbon atoms, a substituted or unsubstituted aryl group containing 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group containing 5 to 50 ring atoms, or a group represented by formula (31).

[0378] Preferably, R 101 To R 110 It is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by formula (31).

[0379] More preferably, R 101 To R 110 It is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, or a group represented by formula (31).

[0380] Most preferably, R 109 and R 110 At least one of them is a group represented by formula (31).

[0381] More preferably, R 109 and R 110 are independently a group represented by formula (31).

[0382] In one embodiment, compound (10) is a compound represented by the following formula (10-1):

[0383]

[0384] In formula (10-1), R 101 To R 108 , L 101 and Ar 101 As defined in formula (10).

[0385] In one embodiment, compound (10) is a compound represented by the following formula (10-2):

[0386]

[0387] In formula (10-2), R 101 , R 103 To R 108 , L 101 and Ar 101 As defined in formula (10).

[0388] In one embodiment, compound (10) is a compound represented by the following formula (10-3):

[0389]

[0390] In formula (10-3),

[0391] R 101A To R 108A is independently a hydrogen atom or a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms;

[0392] L 101A is a single bond or a substituted or unsubstituted arylene group containing 6 to 30 ring carbon atoms, and two L 101A Can be the same or different;

[0393] Ar 101A is a substituted or unsubstituted aryl group containing 6 to 50 ring carbon atoms, and both Ar 101A Can be the same or different.

[0394] In one embodiment, compound (10) is a compound represented by the following formula (10-4):

[0395]

[0396] In formula (10-4),

[0397] L 101 and Ar101 As defined in formula (10);

[0398] R 101A To R 108A is independently a hydrogen atom or a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms;

[0399] X 11 is O, S or N (R 61’ );

[0400] R 61’ is a hydrogen atom, a substituted or unsubstituted alkyl group containing 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group containing 6 to 50 ring carbon atoms;

[0401] R 62’ To R 69’ One is with L 101 Bonding atoms bond;

[0402] No with L 101 Bonded adjacent R 62’ To R 69’ One or more pairs of may be bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring; and

[0403] No with L 101 R is bonded and does not form a substituted or unsubstituted, saturated or unsaturated ring 62’ To R 69’ are independently a hydrogen atom, a substituted or unsubstituted alkyl group comprising 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms.

[0404] In one embodiment, compound (10) is a compound represented by the following formula (10-4A):

[0405]

[0406] In formula (10-4A),

[0407] L 101 and Ar 101 As defined in formula (10);

[0408] R 101A To R 108A is independently a hydrogen atom or a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms;

[0409] X 11 is O, S or N (R 61 );

[0410] R 61is a hydrogen atom, a substituted or unsubstituted alkyl group containing 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group containing 6 to 50 ring carbon atoms;

[0411] Two or more adjacent R 62A To R 69A One or more pairs of may form a substituted or unsubstituted, saturated or unsaturated ring, and R 62A To R 69A Two adjacent ones of form a ring represented by the following formula (10-4A-1); and

[0412] R does not form a substituted or unsubstituted, saturated or unsaturated ring 62A To R 69A are independently a hydrogen atom, a substituted or unsubstituted alkyl group comprising 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms.

[0413]

[0414] In formula (10-4A-1),

[0415] Two atoms bond* each to R 62A To R 69A Two adjacent bonds;

[0416] R 70’ To R 73’ One is with L 101 bonding atoms; and

[0417] No with L 101 Bonded R 70’ To R 73’ are independently a hydrogen atom, a substituted or unsubstituted alkyl group comprising 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms.

[0418] In one embodiment, compound (10) is a compound represented by the following formula (10-6):

[0419]

[0420] In formula (10-6),

[0421] L 101 and Ar 101 As defined in formula (10);

[0422] R 101A To R 108A As defined in formula (10-4);

[0423] R 66’ To R 69’As defined in formula (10-4); and

[0424] X 12 It is O or S.

[0425] In one embodiment, the compound represented by formula (10-6) is a compound represented by the following formula (10-6H):

[0426]

[0427] Wherein in the formula (10-6H),

[0428] L 101 and Ar 101 As defined in formula (10);

[0429] R 66’ To R 69’ As defined in formula (10-4); and

[0430] X 12 It is O or S.

[0431] In one embodiment, the compound represented by formula (10-6) and (10-6H) is a compound represented by the following formula (10-6Ha):

[0432]

[0433] In the formula (10-6Ha),

[0434] L 101 and Ar 101 As defined in formula (10); and

[0435] X 12 It is O or S.

[0436] In one embodiment, the compound represented by formula (10-6), (10-6H) and (10-6Ha) is a compound represented by the following formula (10-6Ha-1) or (10-6Ha-2):

[0437]

[0438] Wherein in the formula (10-6Ha-1) and (10-6Ha-2),

[0439] L 101 and Ar 101 As defined in formula (10); and

[0440] X 12 It is O or S.

[0441] In one embodiment, compound (10) is a compound represented by the following formula (10-7):

[0442]

[0443] In formula (10-7),

[0444] L 101 and Ar 101 As defined in formula (10);

[0445] R 101A To R 108A As defined in formula (10-4);

[0446] X 11 As defined in formula (10-4); and

[0447] R 62’ To R 69’ As defined in formula (10-4), the condition is that R 66’ and R 67’ , R 67’ and R 68’ and R 68’ and R 69’ Any pair of is bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring.

[0448] In one embodiment, compound (10) is a compound represented by the following formula (10-7H):

[0449]

[0450] Wherein in formula (10-7H),

[0451] L 101 and Ar 101 As defined in formula (10);

[0452] X 11 As defined in formula (10-4); and

[0453] R 62’ To R 69’ As defined in formula (10-4), the condition is that R 66’ and R 67’ , R 67’ and R 68’ and R 68’ and R 69’ Any pair of is bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring.

[0454] In one embodiment, compound (10) is a compound represented by the following formula (10-8):

[0455]

[0456] In formula (10-8),

[0457] L 101 and Ar 101 As defined in formula (10);

[0458] R 101A To R 108A As defined in formula (10-4);

[0459] X 12 is O or S; and

[0460] R 66’ To R 69’ As defined in formula (10-4), the condition is that R 66’ and R 67’ , R 67’ and R 68’ and R 68’ and R 69’ Any pair of is bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring.

[0461] In one embodiment, the compound represented by formula (10-8) is a compound represented by the following formula (10-8H):

[0462]

[0463] In the formula (10-8H), L 101 and Ar 101 As defined in formula (10).

[0464] R 66’ To R 69’ As defined in formula (10-4), the condition is that R 66’ and R 67’ , R 67’ and R 68’ and R 68’ and R 69’ Any pair of R is bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring. 66’ and R 67’ , R 67’ and R 68’ and R 68’ and R 69’ Any pair of may preferably be bonded to each other to form an unsubstituted benzene ring; and

[0465] X 12 It is O or S.

[0466] In one embodiment, for the compound represented by formula (10-7), (10-8) or (10-8H), R 66’ and R 67’ , R 67’ and R 68’ and R 68’ and R 69’ Any pair of R is bonded to each other to form a ring represented by the following formula (10-8-1) or (10-8-2), and R does not form a ring represented by the following formula (10-8-1) or (10-8-2). 66’ To R 69’ No substituted or unsubstituted, saturated or unsaturated ring is formed.

[0467]

[0468] In formulas (10-8-1) and (10-8-2),

[0469] Two atoms bond* independently to R 66’ and R 67’ , R 67’ and R 68’ or R 68’ and R 69’ A pair of bonds;

[0470] R 80 To R 83 are independently a hydrogen atom, a substituted or unsubstituted alkyl group comprising 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms; and

[0471] X 13 It is O or S.

[0472] In one embodiment, compound (10) is a compound represented by the following formula (10-9):

[0473]

[0474] In formula (10-9),

[0475] L 101 and Ar 101 As defined in formula (10);

[0476] R 101A To R 108A As defined in formula (10-4);

[0477] R 66’ To R 69’ As defined in formula (10-4), the condition is that R 66’ and R 67’ , R 67’ and R68’ and R 68’ and R 69’ are not bonded to each other and do not form a substituted or unsubstituted, saturated or unsaturated ring; and

[0478] X 12 It is O or S.

[0479] In one embodiment, compound (10) is selected from the group consisting of compounds represented by the following formulae (10-10-1) to (10-10-4).

[0480]

[0481] In formulas (10-10-1H) to (10-10-4H), L 101A and Ar 101A As defined in formula (10-3).

[0482] In one embodiment, in the compound represented by formula (10-1), at least one Ar 101 It is a monovalent group having a structure represented by the following formula (50).

[0483]

[0484] In formula (50),

[0485] X 151 is O, S or C (R 161 )(R 162 ).

[0486] R 151 To R 160 One is with L 101 Single bond bonding.

[0487] Not with L 101 One or more groups of two or more adjacent R 151 To R 154 and one or more groups of two or more adjacent R 155 To R 160 They form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or they do not form a substituted or unsubstituted, saturated or unsaturated ring.

[0488] R 161 and R 162 They form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or they do not form a substituted or unsubstituted, saturated or unsaturated ring.

[0489] R does not form a substituted or unsubstituted, saturated or unsaturated ring 161 and R162 , and not with L 101 R is bonded to a single bond and does not form a substituted or unsubstituted, saturated or unsaturated ring 151 To R 160 The alkyl radicals are independently hydrogen atoms, substituted or unsubstituted alkyl radicals including 1 to 50 carbon atoms, substituted or unsubstituted haloalkyl radicals including 1 to 50 carbon atoms, substituted or unsubstituted alkenyl radicals including 2 to 50 carbon atoms, substituted or unsubstituted alkynyl radicals including 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl radicals including 3 to 50 ring carbon atoms, substituted or unsubstituted alkoxy radicals including 1 to 50 carbon atoms, substituted or unsubstituted alkylene radicals including 1 to 50 carbon atoms, substituted or unsubstituted alkylene radicals including 6 to 8 ... A substituted or unsubstituted aryloxy group having 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 50 carbon atoms, -Si(R121)(R122)(R123), -C(=O)R124, -COOR125, -N(R126)(R127), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0490] Ar is not a monovalent group having a structure represented by formula (50) 101 is a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group comprising 5 to 50 ring atoms.

[0491] In equation (50), it will become 101 The position of the single bond is not particularly limited. In one embodiment, R in formula (50) 151 To R 160 One is with L 101 Single bond bonding.

[0492] In one embodiment, Ar 101 It is the following formula (50-R 152 )、(50-R 153 )、(50-R 154 )、(50-R 157 ) or (50-R 158 ) is a monovalent group represented by

[0493]

[0494] In the formula (50-R 152 )、(50-R 153 )、(50-R 154 )、(50-R 157 ) and (50-R 158), X 151 , R 151 To R 160 As defined in formula (50).

[0495] * is with L 101 Single bond bonding.

[0496] As for the compound represented by formula (10), the following compounds can be given as specific examples. The compound represented by formula (10) is not limited to these specific examples. In the following specific examples, "D" represents a deuterium atom.

[0497]

[0498]

[0499]

[0500]

[0501]

[0502]

[0503]

[0504]

[0505]

[0506]

[0507]

[0508]

[0509]

[0510]

[0511] In the case where the emission layer comprises a compound represented by formula (I) as a dopant and at least one host (wherein the host is preferably as mentioned above, and the host is more preferably at least one compound represented by formula (10)), the content of the at least one compound represented by formula (I) relative to the total mass of the emission layer is preferably 0.5% to 70% by mass, more preferably 0.5 to 30% by mass, further preferably 1 to 30% by mass, further preferably 1 to 20% by mass, particularly preferably 1 to 10% by mass, and further particularly preferably 1 to 5% by mass.

[0512] Relative to the total mass of the emission layer, the content of the at least one main body (wherein the preferred main body is as mentioned above), preferably the at least one compound represented by formula (10), is preferably 30% to 99.9% by mass, more preferably 70 to 99.5% by mass, further preferably 70 to 99% by mass, further preferably 80 to 99% by mass, particularly preferably 90 to 99% by mass, and further particularly preferably 95 to 99% by mass.

[0513] An explanation will be given of the layer configuration of an organic EL device according to one aspect of the present invention.

[0514] The organic EL device according to one aspect of the present invention comprises a cathode, an anode and one or more organic thin film layers containing an emission layer arranged between the cathode and the anode. The organic layer comprises at least one layer composed of an organic compound. Alternatively, the organic layer is formed by laminating a plurality of layers composed of organic compounds. The organic layer may further comprise an inorganic compound in addition to the organic compound.

[0515] At least one organic layer is an emission layer. The organic layer may be configured, for example, as a single emission layer, or may include other layers that may be used in the layer structure of an organic EL device. The layers that may be used in the layer structure of an organic EL device are not particularly limited, but examples thereof include a hole transport region (comprising at least one hole transport layer, and preferably further comprising at least one of a hole injection layer, an electron blocking layer, an exciton blocking layer, etc.), an emission layer, a spacer layer, and an electron transport region (comprising at least one electron transport layer, and preferably further comprising at least one of an electron injection layer, a hole blocking layer, etc.) disposed between the cathode and the emission layer.

[0516] The organic EL device according to one aspect of the present invention can be, for example, a fluorescent or phosphorescent monochromatic light emitting device or a fluorescent / phosphorescent mixed white light emitting device. Preferably, the organic EL device is a fluorescent monochromatic light emitting device, more preferably a blue fluorescent monochromatic light emitting device or a fluorescent / phosphorescent mixed white light emitting device. Blue fluorescence refers to fluorescence at 400 to 500nm (peak maximum), preferably at 430nm to 490nm (peak maximum).

[0517] Furthermore, it may be a simple type device having a single emission unit or a series type device having a plurality of emission units.

[0518] An 'emission unit' in this specification is a minimum unit including organic layers, wherein at least one organic layer is an emission layer and emits light through recombination of injected holes and electrons.

[0519] In addition, the "emission layer" described in this specification is an organic layer having an emission function. The emission layer is, for example, a phosphorescent emission layer, a fluorescent emission layer, etc., preferably a fluorescent emission layer, more preferably a blue fluorescent emission layer, and can be a single layer or a stack of multiple layers.

[0520] The emission unit may be a stacked unit having a plurality of phosphorescent emission layers or fluorescent emission layers. In this case, for example, a spacer layer for preventing excitons generated in the phosphorescent emission layer from diffusing into the fluorescent emission layer may be provided between the respective light emission layers.

[0521] As a simple type organic EL device, a device configuration such as anode / emitting element / cathode can be given.

[0522] An example of a representative layer structure of an emission unit is shown below. The layers in brackets are provided arbitrarily.

[0523] (a) (hole injection layer / ) hole transport layer / fluorescence emission layer ( / electron transport layer / electron injection layer)

[0524] (b) (hole injection layer / hole transport layer / phosphorescent emission layer / electron transport layer / electron injection layer)

[0525] (c) (hole injection layer / hole transport layer / first fluorescent emission layer / second fluorescent emission layer ( / electron transport layer / electron injection layer)

[0526] (d) (hole injection layer / hole transport layer / first phosphorescent layer / second phosphorescent layer ( / electron transport layer / electron injection layer)

[0527] (e) (hole injection layer / ) hole transport layer / phosphorescent emission layer / spacer layer / fluorescent emission layer ( / electron transport layer / electron injection layer)

[0528] (f) (hole injection layer / hole transport layer / first phosphorescent emission layer / second phosphorescent emission layer / spacer layer / fluorescent emission layer ( / electron transport layer / electron injection layer)

[0529] (g) (hole injection layer / hole transport layer / first phosphorescent layer / spacer layer / second phosphorescent emission layer / spacer layer / fluorescent emission layer ( / electron transport layer / electron injection layer)

[0530] (h) (hole injection layer / ) hole transport layer / phosphorescent emission layer / spacer layer / first fluorescent emission layer / second fluorescent emission layer ( / electron transport layer / electron injection layer)

[0531] (i) (hole injection layer / ) hole transport layer / electron blocking layer / fluorescence emission layer ( / electron transport layer / electron injection layer)

[0532] (j) (hole injection layer / ) hole transport layer / electron blocking layer / phosphorescent emission layer ( / electron transport layer / electron injection layer)

[0533] (k) (hole injection layer / ) hole transport layer / exciton blocking layer / fluorescence emission layer ( / electron transport layer / electron injection layer)

[0534] (l) (hole injection layer / hole transport layer / exciton blocking layer / phosphorescent emission layer / electron transport layer / electron injection layer)

[0535] (m) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescence emission layer ( / electron transport layer / electron injection layer)

[0536] (n) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescence emission layer ( / first electron transport layer / second electron transport layer / electron injection layer)

[0537] (o) (hole injection layer / ) first hole transport layer / second hole transport layer / phosphorescent emission layer ( / electron transport layer / electron injection layer)

[0538] (p) (hole injection layer / ) first hole transport layer / second hole transport layer / phosphorescent emission layer ( / first electron transport layer / second electron transport layer / electron injection layer)

[0539] (q) (hole injection layer / ) hole transport layer / fluorescence emission layer / hole blocking layer ( / electron transport layer / electron injection layer)

[0540] (r) (hole injection layer / ) hole transport layer / phosphorescent emission layer / hole blocking layer ( / electron transport layer / electron injection layer)

[0541] (s) (hole injection layer / ) hole transport layer / fluorescence emission layer / exciton blocking layer ( / electron transport layer / electron injection layer)

[0542] (t) (hole injection layer / ) hole transport layer / phosphorescent emission layer / exciton blocking layer ( / electron transport layer / electron injection layer)

[0543] The layer structure of the organic EL device according to one aspect of the present invention is not limited to the above-mentioned examples.

[0544] For example, when the organic EL device has a hole injection layer and a hole transport layer, the hole injection layer is preferably provided between the hole transport layer and the anode. In addition, when the organic EL device has an electron injection layer and an electron transport layer, the electron injection layer is preferably provided between the electron transport layer and the cathode. In addition, the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer can each be formed by a single layer or by a plurality of layers.

[0545] Multiple phosphorescent emission layers, and multiple phosphorescent emission layers and fluorescent emission layers can be emission layers that emit different colors from each other. For example, the emission unit (F) may include a hole transport layer / a first phosphorescent layer (red light emission) / a second phosphorescent emission layer (green light emission) / a spacer layer / a fluorescent emission layer (blue light emission) / an electron transport layer.

[0546] An electron blocking layer may be provided between each light emitting layer and a hole transport layer or a spacer layer. In addition, a hole blocking layer may be provided between each emission layer and an electron transport layer. By providing an electron blocking layer or a hole blocking layer, it is possible to confine electrons or holes in the emission layer, thereby improving the probability of carrier recombination in the emission layer and improving the luminous efficiency.

[0547] As a representative device configuration of the tandem organic EL device, for example, a device configuration such as anode / first emission unit / intermediate layer / second emission unit / cathode can be given.

[0548] The first emitting unit and the second emitting unit are independently selected from, for example, the emitting units described above.

[0549] The intermediate layer is also generally referred to as an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron-withdrawing layer, a connecting layer, a connector layer, or an intermediate insulating layer. The intermediate layer is a layer that supplies electrons to the first emission unit and holes to the second emission unit, and can be formed of a known material.

[0550] Figure 1 A schematic configuration of an example of an organic EL device of the present invention is shown. The organic EL device 1 includes a substrate 2, an anode 3, a cathode 4, and an emission unit 10 disposed between the anode 3 and the cathode 4. The emission unit 10 includes an emission layer 5, which preferably includes a host material and a dopant. A hole injection and transport layer 6 and the like may be provided between the emission layer 5 and the anode 3, and an electron injection layer 8 and an electron transport layer 7 and the like (electron injection and transport unit 11) may be provided between the emission layer 5 and the cathode 4. An electron blocking layer may be provided on the anode 3 side of the emission layer 5, and a hole blocking layer may be provided on the cathode 4 side of the emission layer 5. Due to such a configuration, electrons or holes may be confined in the emission layer 5, thereby improving the possibility of generating excitons in the emission layer 5.

[0551] The functions, materials, and the like of the respective layers constituting the organic EL device described in this specification will be explained below.

[0552] (Substrate)

[0553] The substrate is used as a carrier of the organic EL device. The substrate preferably has a light transmittance of 50% or more in the visible light region with a wavelength of 400 to 700nm, and a smooth substrate is preferred. Examples of substrate materials include soda-lime glass, aluminosilicate glass, quartz glass, plastics, etc. As a substrate, a flexible substrate can be used. A flexible substrate refers to a substrate that can be bent (flexible), examples of which include plastic substrates, etc. Specific examples of materials for forming plastic substrates include polycarbonate, polyallylate, polyether sulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, polyethylene naphthalate, etc. Inorganic vapor deposition films can also be used.

[0554] (anode)

[0555] As the anode, for example, a metal having a high work function (specifically, 4.0 eV or more), an alloy, a conductive compound, a mixture thereof, etc. are preferably used. Specific examples of the anode material include indium oxide-tin oxide (ITO: indium tin oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide or zinc oxide, graphene, etc. In addition, it is also possible to use gold, silver, platinum, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, and nitrides of these metals (e.g., titanium oxide).

[0556] These materials are usually deposited on a substrate by sputtering to form an anode. For example, indium oxide-zinc oxide can be formed by sputtering using a target material to which 1 to 10% by mass of zinc oxide is added relative to indium oxide. In addition, indium oxide containing tungsten oxide or zinc oxide can be formed by sputtering using a target material to which 0.5 to 5% by mass of tungsten oxide or 0.1 to 1% by mass of zinc oxide is added relative to indium oxide.

[0557] As other methods for forming the anode, there can be given a vacuum deposition method, a coating method, an inkjet method, a spin coating method, etc. When a silver paste or the like is used, a coating method, an inkjet method, etc. can be used.

[0558] The hole injection layer formed in contact with the anode is formed by using a material that easily injects holes regardless of the work function of the anode. Therefore, in the anode, it is possible to use common electrode materials such as metals, alloys, conductive compounds and mixtures thereof. Specifically, materials with a small work function are used, such as alkali metals such as lithium and cesium; alkaline earth metals such as calcium and strontium; alloys containing these metals (such as magnesium-silver and aluminum-lithium); rare earth metals such as europium and ytterbium; and alloys containing rare earth metals.

[0559] (Hole transport layer) / (Hole injection layer)

[0560] The hole transport layer is an organic layer formed between the emission layer and the anode, and has the function of transporting holes from the anode to the emission layer. If the hole transport layer is composed of multiple layers, the organic layer closer to the anode can generally be defined as a hole injection layer. The hole injection layer has the function of effectively injecting holes from the anode into the organic layer unit. The hole injection layer is generally used to stabilize the hole injection from the anode to the hole transport layer generally composed of an organic material. An organic material having good contact with the anode or an organic material having p-type doping is preferably used for the hole injection layer.

[0561] P-type doping is usually composed of one or more p-type dopant materials and one or more host materials. The host material preferably has a shallower HOMO energy level, and the p-type dopant preferably has a deeper LUMO energy level to enhance the carrier density of the layer. The specific example of the p-type dopant is the acceptor material mentioned below. Suitable host materials are the hole transport materials mentioned below, preferably aromatic or heterocyclic amine compounds.

[0562] An acceptor material or a condensed aromatic hydrocarbon material or a condensed heterocyclic ring having high planarity is preferably used as the p-type dopant material of the hole injection layer.

[0563] Specific examples of acceptor materials are quinone compounds having one or more electron withdrawing groups, such as F4TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane) and 1,2,3-tris[(cyano)(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane; hexa-azatriphenylene compounds having one or more electron withdrawing groups, such as hexa-azatriphenylene-hexanenitrile; aromatic compounds having one or more electron withdrawing groups; and arylboron compounds having one or more electron withdrawing groups. Preferred p-type dopants are quinone compounds having one or more electron withdrawing groups, such as F4TCNQ, 1,2,3-tris[(cyano)(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane.

[0564] The ratio of the p-type dopant relative to the host material is preferably less than 20% by mole, more preferably less than 10%, such as 1%, 3% or 5%.

[0565] The hole transport layer generally serves to efficiently inject and transport holes, and preferably uses an aromatic or heterocyclic amine compound.

[0566] A specific example of the compound for the hole transport layer is represented by the general formula (H),

[0567]

[0568] in

[0569] Ar 1’ To Ar 3’Each independently represents a substituted or unsubstituted aryl group having 5 to 50 carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, a fluorenyl group, a spirobifluorenyl group, an indenofluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophene group, a carbazole-substituted aryl group, a dibenzofuran-substituted aryl group or a dibenzothiophene-substituted aryl group; selected from Ar 1’ To Ar 3’ Two or more substituents of may be bonded to each other to form a ring structure such as a carbazole ring structure or an acridine ring structure.

[0570] Preferably, Ar 1’ To Ar 3’ At least one of the substituted groups has another aromatic or heterocyclic amine substituent, more preferably Ar 1’ With an additional arylamino substituent, in this case Ar 1’ Preferably represents a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group. Specific examples of hole transport materials are

[0571]

[0572] wait.

[0573] A second hole transport layer is preferably inserted between the first hole transport layer and the emission layer to enhance device performance by blocking excess electrons or excitons.

[0574] Specific examples of the second hole transport layer are the same as those of the first hole transport layer. Preferably, the second hole transport layer has a higher triplet energy to block triplet excitons, especially for phosphorescent devices, such as bicarbazole compounds, benzidine compounds, triphenyleneamine compounds, fluorenylamine compounds, carbazole-substituted arylamine compounds, dibenzofuran-substituted arylamine compounds, and dibenzothiophene-substituted arylamine compounds.

[0575] (Emission Layer)

[0576] The emission layer is a layer containing a substance (emitter material or dopant material) with high emission properties. As a dopant material, various materials can be used. For example, fluorescent emission compounds (fluorescent dopants), phosphorescent emission compounds (phosphorescent dopants), etc. can be used. The fluorescent emission compound is a compound that can emit light from a singlet excited state, and the emission layer containing the fluorescent emission compound is called a fluorescent emission layer. In addition, the phosphorescent emission compound is a compound that can emit light from a triplet excited state, and the emission layer containing the phosphorescent emission compound is called a phosphorescent emission layer.

[0577] Preferably, the emission layer in the organic EL device of the present application comprises the compound of formula (I) as a dopant material.

[0578] The emission layer preferably comprises at least one dopant material and at least one host material to enable it to emit light efficiently. In some documents, the dopant material is referred to as a guest material, an emitter or an emission material. In some documents, the host material is referred to as a matrix material.

[0579] A single emissive layer may contain multiple dopant materials and multiple host materials. Additionally, there may be multiple emissive layers.

[0580] In this specification, a host material combined with a fluorescent dopant is referred to as a "fluorescent host", and a host material combined with a phosphorescent dopant is referred to as a "phosphorescent host". Note that fluorescent hosts and phosphorescent hosts are not only classified by molecular structure. A phosphorescent host is a material for forming a phosphorescent emission layer containing a phosphorescent dopant, but it does not mean that it cannot be used as a material for forming a fluorescent emission layer. The same applies to fluorescent hosts.

[0581] In one embodiment, it is preferred that the emission layer contains the compound represented by formula (I) according to the present invention (hereinafter, these compounds may be referred to as "compound (I)"). More preferably, it is contained as a dopant material. In addition, it is preferred that compound (I) is contained in the emission layer as a fluorescent dopant. Further, it is preferred that compound (I) is contained in the emission layer as a blue fluorescent dopant.

[0582] In one embodiment, there is no particular restriction on the content of the compound (I) as a dopant material in the emission layer. In view of sufficient emission and concentration quenching, the content is preferably 0.5 to 70% by mass, more preferably 0.8 to 30% by mass, further preferably 1 to 30% by mass, further preferably 1 to 20% by mass, particularly preferably 1 to 10% by mass, further particularly preferably 1 to 5% by mass, and further particularly preferably 2 to 4% by mass, relative to the mass of the emission layer.

[0583] (Fluorescent dopant)

[0584] Examples of fluorescent dopants other than compound (I) include condensed polycyclic aromatic compounds, styrylamine compounds, condensed ring amine compounds, boron-containing compounds, pyrrole compounds, indole compounds, and carbazole compounds. Among them, condensed ring amine compounds, boron-containing compounds, and carbazole compounds are preferred.

[0585] As the fused ring amine compound, there can be given diaminopyrene compounds, diamino Compounds, diaminoanthracene compounds, diaminofluorene compounds, diaminofluorene compounds fused with one or more benzofuran skeletons, and the like.

[0586] As the boron-containing compound, a pyrromethene compound, a triphenylborane compound and the like can be given.

[0587] As the blue fluorescent dopant, for example, pyrene compounds, styrylamine compounds, Compounds, fluoranthene compounds, fluorene compounds, diamine compounds, triarylamine compounds, etc. Specifically, N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenyldistyrene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthracenyl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthracenyl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCBAPA), etc. can be given.

[0588] As the green fluorescent dopant, for example, aromatic amine compounds can be given. Specifically, for example, N-(9,10-diphenyl-2-anthracenyl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthracenyl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DP APA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), etc.

[0589] As the red fluorescent dopant, there can be given a tetracene compound, a diamine compound, etc. Specifically, there can be given N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), etc.

[0590] (Phosphorescent Dopant)

[0591] As the phosphorescent dopant, a phosphorescent heavy metal complex and a phosphorescent rare earth metal complex can be given.

[0592] As the heavy metal complex, there can be given an iridium complex, an osmium complex, a platinum complex, etc. The heavy metal complex is, for example, an ortho-metalated complex of a metal selected from iridium, osmium, and platinum.

[0593] Examples of rare earth metal complexes include terbium complexes, europium complexes, etc. Specifically, terbium (III) tris(acetylacetonate) (monophenanthroline) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedione) (monophenanthroline) europium (III) (abbreviation: Eu(DBM)3(Phen)), tris[1-(2-thenoyl)-3,3,3-trifluoroacetone] (monophenanthroline) europium (III) (abbreviation: Eu(TTA)3(Phen)), etc. can be given. These rare earth metal complexes are preferred as phosphorescent dopants because rare earth metal ions emit light due to electron transitions between different multiplicities.

[0594] As the blue phosphorescent dopant, for example, iridium complexes, osmium complexes, platinum complexes, etc. can be given. Specifically, bis[2-(4',6'-difluorophenyl)pyridine-N, C2']iridium(III)tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridine-N, C2']picolinic acid iridium(III) (abbreviation: Ir(CF3ppy)2(pic)), bis[2-(4',6'-difluorophenyl)pyridine-N, C2']acetylacetonate iridium(III) (abbreviation: FIracac), etc. can be given.

[0595] As green phosphorescent dopants, for example, iridium complexes can be given, and specifically, tris(2-phenylpyridine-N,C2')iridium(III) (abbreviation: Ir(ppy)3), bis(1,2-diphenyl-1H-benzimidazole)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)), and the like can be given.

[0596] As the red phosphorescent dopant, there can be given an iridium complex, a platinum complex, a terbium complex, a europium complex, etc. Specifically, there can be given bis[2-(2'-benzo[4,5-α]thienyl)pyridine-N,C3']acetylacetonate iridium(III) (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinoline-N,C2')acetylacetonate iridium(III) (abbreviation: Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP), etc.

[0597] As mentioned above, the emissive layer preferably comprises at least one compound (I) as dopant.

[0598] (Main material)

[0599] As the host material, for example, there can be given metal complexes such as aluminum complexes, beryllium complexes and zinc complexes; heterocyclic compounds such as indole compounds, pyridine compounds, pyrimidine compounds, triazine compounds, quinoline compounds, isoquinoline compounds, quinazoline compounds, dibenzofuran compounds, dibenzothiophene compounds, oxadiazole compounds, benzimidazole compounds, phenanthroline compounds; condensed polycyclic aromatic hydrocarbon (PAH) compounds such as naphthalene compounds, triphenylene compounds, carbazole compounds, anthracene compounds, phenanthrene compounds, pyrene compounds, compounds, tetracene compounds, fluoranthene compounds; and aromatic amine compounds such as triarylamine compounds and condensed polycyclic aromatic amine compounds. A plurality of types of host materials may be used in combination.

[0600] As the fluorescent host, a compound having a singlet energy level higher than that of the fluorescent dopant is preferred. For example, heterocyclic compounds, condensed aromatic compounds, etc. can be given. As the condensed aromatic compound, anthracene compounds, pyrene compounds, Compounds, tetracene compounds, etc. are preferred. Anthracene compounds are preferably used as a blue fluorescent host.

[0601] In the case of using compound (I) as at least one dopant material, the preferred host material is a substituted or unsubstituted polycyclic aromatic hydrocarbon (PAH) compound, a substituted or unsubstituted polycyclic heteroaromatic compound, a substituted or unsubstituted anthracene compound or a substituted or unsubstituted pyrene compound, preferably a substituted or unsubstituted anthracene compound or a substituted or unsubstituted pyrene compound, more preferably a substituted or unsubstituted anthracene compound, and most preferably an anthracene compound represented by formula (10) as mentioned above.

[0602] As the phosphorescent host, a compound having a triplet energy level higher than that of the phosphorescent dopant is preferred. For example, metal complexes, heterocyclic compounds, condensed aromatic compounds, etc. can be given. Among them, indole compounds, carbazole compounds, pyridine compounds, pyrimidine compounds, triazine compounds, quinolone compounds, isoquinoline compounds, quinazoline compounds, dibenzofuran compounds, dibenzothiophene compounds, naphthalene compounds, triphenylene compounds, phenanthrene compounds, fluoranthene compounds, etc. can be given.

[0603] (Electron transport layer) / (Electron injection layer)

[0604] The electron transport layer is an organic layer formed between the emission layer and the cathode and has the function of transporting electrons from the cathode to the emission layer. When the electron transport layer is formed of multiple layers, the organic layer or inorganic layer closer to the cathode is generally defined as the electron injection layer (see, for example Figure 1Layer 8 therein, where the electron injection layer 8 and the electron transport layer 7 form an electron injection and transport unit 11). The electron injection layer has the function of effectively injecting electrons from the cathode into the organic layer unit. Preferred electron injection materials are alkali metals, alkali metal compounds, alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes.

[0605] According to one embodiment, the electron transport layer preferably further includes one or more layers, such as a second electron transport layer, an electron injection layer for enhancing the efficiency and lifetime of the device, a hole blocking layer, an exciton blocking layer, or a triplet blocking layer.

[0606] According to one embodiment, it is preferred to include an electron-donating dopant in the interface region between the cathode and the emission unit. Due to such a configuration, the organic EL device can have increased brightness or long lifetime. Here, the electron-donating dopant refers to a dopant having a metal with a work function of 3.8 eV or less. As specific examples thereof, at least one selected from alkali metals, alkali metal complexes, alkali metal compounds, alkaline earth metals, alkaline earth metal complexes, alkaline earth metal compounds, rare earth metals, rare earth metal complexes, and rare earth metal compounds, etc. can be mentioned.

[0607] As alkali metals, Li (work function: 2.9 eV), Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), Cs (work function: 1.95 eV), etc. can be given. Alkali metals with a work function of 2.9 eV or less are particularly preferred. Among them, K, Rb, and Cs are preferred. Rb or Cs is further preferred. Cs is most preferred. As alkaline earth metals, Ca (work function: 2.9 eV), Sr (work function: 2.0 eV to 2.5 eV), Ba (work function: 2.52 eV), etc. can be given. Alkaline earth metals with a work function of 2.9 eV or less are particularly preferred. As rare earth metals, Sc, Y, Ce, Tb, Yb, etc. can be given. Rare earth metals with a work function of 2.9 eV or less are particularly preferred.

[0608] Examples of alkali metal compounds include alkali metal oxides such as Li2O, Cs2O, or K2O, and alkali metal halides such as LiF, NaF, CsF, and KF. Among them, LiF, Li2O, and NaF are preferred. Examples of alkaline earth metal compounds include BaO, SrO, CaO, and their mixtures, such as Ba x Sr 1-x O (0 < x < 1) and Ba x Ca 1-x O (0 < x < 1). Among them, BaO, SrO, and CaO are preferred. Examples of rare earth metal compounds include YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3, and TbF3. Among them, YbF3, ScF3, and TbF3 are preferred.

[0609] There is no particular restriction on alkali metal complex, alkaline earth metal complex and rare earth metal complex, as long as they contain at least one of alkali metal ion, alkaline earth metal ion and rare earth metal ion as metal ion. Meanwhile, preferred examples of the part include but are not limited to quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole, hydroxydiarylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, hydroxyfluoroborane (hydroxyfluborane), bipyridine, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, β-diketone and azomethine.

[0610] Regarding the addition form of the electron donating dopant, the electron donating dopant is preferably formed in the shape of a layer or an island in the interface region. A preferred method for forming is a method in which an organic compound (light emitting material or electron injecting material) for forming the interface region is deposited by a resistance heating deposition method while depositing the electron donating dopant, thereby dispersing the electron donating dopant in the organic compound.

[0611] In the case where the electron-donating dopant is formed into a layer shape, the light-emitting material or electron injection material acting as an organic layer in the interface is formed into a layer shape. Thereafter, the reductive dopant is deposited separately by a resistance heating deposition method to form a layer preferably having a thickness of 0.1nm to 15nm. In the case where the electron-donating dopant is formed into an island shape, the light-emitting material or electron injection material acting as an organic layer in the interface is formed into an island shape. Thereafter, the electron-donating dopant is deposited separately by a resistance heating deposition method to form an island preferably having a thickness of 0.05nm to 1nm. As an electron transport material other than the compound of formula (I) used in the electron transport layer, an aromatic heterocyclic compound having one or more heteroatoms in the molecule can be preferably used. In particular, nitrogen-containing heterocyclic compounds are preferred.

[0612] According to one embodiment, the electron transport layer preferably comprises a nitrogen-containing heterocyclic metal chelate.

[0613] According to another embodiment, the electron transport layer preferably contains a substituted or unsubstituted nitrogen-containing heterocyclic compound. Specific examples of preferred heterocyclic compounds for the electron transport layer are 6-membered azine compounds; such as pyridine compounds, pyrimidine compounds, triazine compounds, pyrazine compounds, preferably pyrimidine compounds or triazine compounds; 6-membered fused azine compounds, such as quinolone compounds, isoquinoline compounds, quinoxaline compounds, quinazoline compounds, phenanthroline compounds, benzoquinoline compounds, benzisoquinoline compounds, dibenzoquinoxaline compounds, preferably quinolone compounds, isoquinoline compounds, phenanthroline compounds; 5-membered heterocyclic compounds, such as imidazole compounds, oxazole compounds, oxadiazole compounds, triazole compounds, thiazole compounds, thiadiazole compounds; fused imidazole compounds, such as benzimidazole compounds, imidazopyridine compounds, naphthymidazole compounds, benzimidazole and phenanthridine compounds, benzimidazole and benzimidazole compounds, preferably benzimidazole compounds, imidazopyridine compounds or benzimidazole and phenanthridine compounds.

[0614] According to another embodiment, the electron transport layer preferably comprises p1 Ar p2 Ar P3 A phosphine oxide compound wherein P=O.

[0615] Ar p1 To Ar p3 are substituents of the phosphorus atom, and each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0616] According to another embodiment, the electron transport layer preferably comprises an aromatic compound. Specific examples of preferred aromatic compounds for the electron transport layer are oligophenylene compounds, naphthalene compounds, fluorene compounds, fluoranthenyl, anthracene compounds, phenanthrene compounds, pyrene compounds, triphenylene compounds, benzanthracene compounds, Compounds, benzphenanthrene compounds, tetracene compounds and benzophenone Compounds, preferably anthracene compounds, pyrene compounds and fluoranthene compounds.

[0617] (cathode)

[0618] For the cathode, metals, alloys, conductive compounds, and mixtures thereof each having a small work function (specifically, a work function of 3.8 eV or less) are preferably used. Specific examples of materials for the cathode include alkali metals such as lithium and cesium; alkaline earth metals such as magnesium, calcium, and strontium; aluminum, alloys containing these metals (e.g., magnesium-silver, aluminum-lithium); rare earth metals such as europium and ytterbium; and alloys containing rare earth metals.

[0619] The cathode is usually formed by vacuum vapor deposition or sputtering. In addition, in the case of using silver paste or the like, a coating method, an inkjet method, or the like can be used.

[0620] In addition, the cathode can be formed using various conductive materials selected independently of the work function, such as silver, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, and these conductive materials can be made into films using sputtering, inkjet, spin coating, etc.

[0621] (Insulation layer)

[0622] In organic EL devices, due to the application of an electric field to the film, pixel defects based on leakage or short circuit are easily generated. In order to prevent this, it is preferred to insert an insulating thin layer between a pair of electrodes. Examples of materials for insulating layers include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide and vanadium oxide. Its mixture can be used for insulating layers, and laminates including multiple layers of these materials can also be used for insulating layers.

[0623] (Spacer layer)

[0624] The spacer layer is a layer disposed between the fluorescent emission layer and the phosphorescent emission layer when the fluorescent emission layer and the phosphorescent emission layer are stacked to prevent the excitons generated in the phosphorescent emission layer from diffusing to the fluorescent emission layer or to adjust the carrier balance. In addition, a spacer layer may be provided between multiple phosphorescent emission layers.

[0625] Since the spacer layer is disposed between the emission layers, the material used for the spacer layer is preferably a material having both electron transport capability and hole transport capability. In order to prevent the triplet energy from diffusing in the adjacent phosphorescent emission layer, the spacer layer preferably has a triplet energy of 2.6 eV or more. As the material used for the spacer layer, the same material as that used in the above-mentioned hole transport layer can be given.

[0626] (Electron blocking layer, hole blocking layer, exciton blocking layer)

[0627] An electron blocking layer, a hole blocking layer, an exciton (triplet) blocking layer, or the like may be provided adjacent to the emission layer.

[0628] The electron blocking layer has the function of preventing electrons from leaking from the emission layer to the hole transport layer. The hole blocking layer has the function of preventing holes from leaking from the emission layer to the electron transport layer. In order to improve the hole blocking ability, it is preferred to use a material with a deep HOMO energy level. The exciton blocking layer has the function of preventing the excitons generated in the emission layer from diffusing to the adjacent layers and confining the excitons in the emission layer. In order to improve the triplet blocking ability, it is preferred to use a material with a high triplet energy level.

[0629] (Method of forming layers)

[0630] Unless otherwise specified, the method for forming each layer of the organic EL device of the present invention is not particularly limited. Known film forming methods such as dry film forming methods, wet film forming methods, etc. can be used. Specific examples of dry film forming methods include vacuum deposition methods, sputtering methods, plasma methods, ion plating methods, etc. Specific examples of wet film forming methods include various coating methods, such as spin coating, dipping methods, flow coating methods, inkjet methods, etc.

[0631] (Film thickness)

[0632] Unless otherwise specified, the film thickness of each layer of the organic EL device of the present invention is not particularly limited. If the film thickness is too small, defects such as pinholes are likely to occur, making it difficult to obtain sufficient brightness. If the film thickness is too large, a high driving voltage needs to be applied, so that the efficiency is reduced. In this regard, the film thickness is preferably 0.1nm to 10μm, more preferably 5nm to 0.2μm.

[0633] (Electronic device (electronic equipment))

[0634] The present invention further relates to electronic devices (electronic devices) comprising the organic electroluminescent device according to the present application. Examples of electronic devices include display components such as organic EL panel modules; display devices of televisions, mobile phones, smart phones, personal computers, etc.; and emitting devices of lighting equipment and vehicle lighting devices. Example

[0635] Next, the present invention is explained in more detail according to the following Synthesis Examples, Examples and Comparative Examples, which should not be construed as limiting the scope of the present invention.

[0636] Unless otherwise indicated, the percentages and ratios mentioned in the following examples are by weight % and weight ratio.

[0637] I. Synthesis Example

[0638] All experiments were carried out in a protective gas atmosphere.

[0639] Compound 1

[0640] Intermediate 1

[0641]

[0642] In a 1 L degassed 3-neck round bottom flask were added 1,2-dibromo-3-iodo-5-methylbenzene (35.1 g, 93 mmol), bis(4-(tert-butyl)phenyl)amine (25 g, 89 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.66 g, 1.78 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) (4.2 g, 7.1 mmol) and sodium tert-butoxide (12.3 g, 124 mmol). Toluene (500 mL) was then added and the reaction was heated under nitrogen at an oil bath temperature of 130° C. for 16 hours. The reaction was then allowed to cool to room temperature and the mixture was filtered through hyflo. The mother liquor was washed with saturated aqueous sodium bicarbonate, water, and then with saturated aqueous sodium chloride and dried over magnesium sulfate. The solution was then filtered through a pad of silica, rinsed with toluene. The solvent was removed under reduced pressure. The crude product was triturated with 2-propanol. The precipitate thus formed was then recrystallized from toluene-2-propanol to obtain the desired product (27.4 g, 58% yield) as a white solid, which was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0643] ESI-MS: calculated value for C27H31Br2N = 527, found mass = 528 (M+1)

[0644] Intermediate 2

[0645]

[0646] The synthetic procedure of Intermediate 1 was repeated except that Intermediate 1 was used instead of 1,2-dibromo-3-iodo-5-methylbenzene, 4-(tert-butyl)-N-(4-chlorophenyl)aniline was used instead of bis(4-(tert-butyl)phenyl)amine, and bis(tri-tert-butylphosphanyl)palladium was used instead of tris(dibenzylideneacetone)dipalladium(0) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane). The obtained Intermediate 2 (63% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0647] ESI-MS: calculated value for C43H48BrClN2 = 706, found mass = 707 (M+1)

[0648] Intermediate 3

[0649]

[0650] Intermediate 2 (4 g, 5.65 mmol) was dissolved in tert-butylbenzene (100 ml) and cooled in a 0°C water-ice bath under N2. Tert-butyl lithium (5.95 ml, 11.30 mmol) was added dropwise via a syringe, and the resulting reaction mixture was allowed to warm to room temperature. After 2 hours, the lithiation of intermediate 2 was complete. The reaction mixture was cooled at -30°C, and then boron tribromide (1M heptane solution, 1.869 ml, 19.77 mmol) was added dropwise. After the addition was complete, the reaction was allowed to warm to room temperature. Diisopropylethylamine (4.93 ml, 28.2 mmol) was then added to the reaction, and the mixture was heated at an oil bath temperature of 165°C for 2 hours. After cooling to room temperature, the reaction was quenched by adding a saturated aqueous ammonium chloride solution. The organic phase was separated, subsequently washed with a saturated aqueous sodium bicarbonate solution, water, and then washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The crude reaction product was then purified by silica gel chromatography eluting with a gradient of 100% heptane to 10% dichloromethane / heptane. Intermediate 3 (0.85 g, 23% yield) was isolated as a yellow solid and characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0651] ESI-MS: calculated value for C43H46BClN2 = 636, found mass = 637 (M+1)

[0652] Compound 1

[0653]

[0654] Intermediate 3 (0.65 g, 1 mmol) was combined with dibenzo[b,d]furan-3-ylboronic acid (0.32 g, 1.5 mmol), palladium(II) acetate (5.7 mg, 0.026 mmol), dicyclohexyl[2',4',6'-tri(propan-2-yl)[1,1'-biphenyl]-2-yl]phosphane (49 mg, 0.1 mmol) and cesium carbonate (0.83 g, 2.55 mmol) in a pre-dried schlenk flask and degassed under N2. Toluene (6 mL), EtOH (2.25 mL) and water (2.25 mL) were then added and the reaction was heated at an oil bath temperature of 100°C under N2 atmosphere overnight. The reaction was cooled to room temperature, diluted with toluene, washed sequentially with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and the solution was directly filtered through silica gel, washing with toluene. The solvent was evaporated under reduced pressure, and the crude residue was stirred in acetone at room temperature for 1 hour. Compound 1 (0.7 g, 89% yield) was isolated by filtration and characterized by ESI-MS (electrospray ionization mass spectrometry), the maximum ultraviolet absorption wavelength in toluene (UV (PhMe) λonset) and the maximum fluorescence wavelength in toluene (FL (PhMe, λex = 330 nm) λmax). The results are shown below.

[0655] ESI-MS: Calculated value for C55H53BN2O = 768, found mass = 769 (M+1)

[0656] UV(PhMe)λonset:458nm

[0657] FL(PhMe,λex=400nm)λmax:455nm

[0658] Compound 2

[0659]

[0660] The synthetic procedure of intermediate 1 was repeated except that 3-(tert-butyl)-N-(4-chlorophenyl)aniline was used instead of bis(4-(tert-butyl)phenyl)amine and tri-tert-butylphosphonium tetrafluoroborate was used instead of (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane). The obtained intermediate 4 (75% yield) was characterized by APCI-MS (atmospheric pressure chemical ionization). The results are shown below.

[0661] APCI-MS: calculated value for C39H39BrCl2N2 = 684, found mass = 685 (M+1).

[0662]

[0663] The synthetic procedure of Intermediate 3 was repeated except that Intermediate 4 was used instead of Intermediate 2. The obtained Intermediate 5 (34% yield) was characterized by APCI-MS (Atmospheric Pressure Chemical Ionization). The results are shown below.

[0664] APCI-MS: Calculated value for C39H37BCl2N2 = 614, found mass = 615 (M+1)

[0665]

[0666] The synthetic procedure of compound 1 was repeated, except that intermediate 5 was used instead of intermediate 3 and dibenzo[b,d]furan-4-ylboronic acid was used instead of dibenzo[b,d]furan-3-ylboronic acid. The obtained compound 2 (91%) was characterized by ESI-MS (electrospray ionization mass spectrometry), maximum ultraviolet absorption wavelength in toluene (UV(PhMe)λonset) and maximum fluorescence wavelength in toluene (FL(PhMe,λex=330nm)λmax). The results are shown below.

[0667] ESI-MS: Calculated value for C63H51BN2O2 = 878, found mass = 879 (M+1)

[0668] UV(PhMe)λonset:449nm

[0669] FL(PhMe,λex=400nm)λmax:446nm

[0670] Compound 3

[0671]

[0672] The synthetic procedure of Intermediate 4 was repeated except that 4-(tert-butyl)-N-(4-chlorophenyl)aniline was used instead of 3-(tert-butyl)-N-(4-chlorophenyl)aniline. The obtained Intermediate 6 (88%) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0673] ESI-MS: Calculated value for C39H39BrCl2N2 = 684, found mass = 685 (M+1)

[0674]

[0675] The synthetic procedure of Intermediate 3 was repeated except that Intermediate 6 was used instead of Intermediate 2. The obtained Intermediate 7 (34% yield) was characterized by APCI-MS (Atmospheric Pressure Chemical Ionization). The results are shown below.

[0676] APCI-MS: Calculated value for C39H37BCl2N2 = 614, found mass = 615 (M+1)

[0677]

[0678] The synthetic procedure of compound 1 was repeated, except that intermediate 7 was used instead of intermediate 3. The obtained compound 3 (73%) was characterized by ESI-MS (electrospray ionization mass spectrometry), the maximum ultraviolet absorption wavelength in toluene (UV (PhMe) λonset) and the maximum fluorescence wavelength in toluene (FL (PhMe, λex = 330 nm) λmax). The results are shown below.

[0679] ESI-MS: Calculated value for C63H51BN2O2 = 878, found mass = 879 (M+1)

[0680] UV(PhMe)λonset:458nm

[0681] FL(PhMe,λex=400nm)λmax:454nm

[0682] Compound 4

[0683]

[0684] The synthetic procedure of Intermediate 1 was repeated except that 1,2-dibromo-5-(tert-butyl)-3-iodobenzene was used instead of 1,2-dibromo-3-iodo-5-methylbenzene. The obtained Intermediate 8 (78%) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0685] ESI-MS: calculated value for C30H37Br2N = 569, found mass = 570 (M+1)

[0686]

[0687] The synthetic procedure of Intermediate 1 was repeated except that Intermediate 8 was used instead of 1,2-dibromo-3-iodo-5-methylbenzene, 4-(tert-butyl)-N-(4-chlorophenyl)aniline was used instead of bis(4-(tert-butyl)phenyl)amine, and bis(tri-tert-butylphosphanyl)palladium was used instead of tris(dibenzylideneacetone)dipalladium(0) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane). The obtained Intermediate 9 (72% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0688] ESI-MS: calculated value for C46H54BrClN2 = 748, found mass = 749 (M+1)

[0689]

[0690] The synthetic procedure of Intermediate 3 was repeated except that Intermediate 9 was used instead of Intermediate 2. The obtained Intermediate 10 (34% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0691] ESI-MS: calculated value for C46H52BClN2 = 678, found mass = 679 (M+1)

[0692]

[0693] The synthetic procedure of compound 1 was repeated, except that intermediate 10 was used instead of intermediate 3. The obtained compound 4 (92%) was characterized by ESI-MS (electrospray ionization mass spectrometry), the maximum ultraviolet absorption wavelength in toluene (UV (PhMe) λonset) and the maximum fluorescence wavelength in toluene (FL (PhMe, λex = 330 nm) λmax). The results are shown below.

[0694] ESI-MS: Calculated value for C58H59BN2O = 810, found mass = 811 (M+1)

[0695] UV(PhMe)λonset:463nm

[0696] FL(PhMe,λex=400nm)λmax:459nm

[0697] Compound 5

[0698]

[0699] The synthetic procedure of Intermediate 1 was repeated except that Intermediate 8 was used instead of 1,2-dibromo-3-iodo-5-methylbenzene, 3-(tert-butyl)-N-(4-chlorophenyl)aniline was used instead of bis(4-(tert-butyl)phenyl)amine, and bis(tri-tert-butylphosphanyl)palladium was used instead of tris(dibenzylideneacetone)dipalladium(0) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane). The obtained Intermediate 11 (73% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0700] ESI-MS: calculated value for C46H54BrClN2 = 748, found mass = 749 (M+1)

[0701]

[0702] The synthetic procedure of Intermediate 3 was repeated except that Intermediate 11 was used instead of Intermediate 2. The obtained Intermediate 12 (42% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0703] ESI-MS: calculated value for C46H52BClN2 = 678, found mass = 679 (M+1)

[0704]

[0705] The synthetic procedure of compound 1 was repeated, except that intermediate 12 was used instead of intermediate 3. The obtained compound 5 (92%) was characterized by ESI-MS (electrospray ionization mass spectrometry), the maximum ultraviolet absorption wavelength in toluene (UV (PhMe) λonset) and the maximum fluorescence wavelength in toluene (FL (PhMe, λex = 330 nm) λmax). The results are shown below.

[0706] ESI-MS: Calculated value for C58H59BN2O = 810, found mass = 811 (M+1)

[0707] UV(PhMe)λonset:456nm

[0708] FL(PhMe,λex=400nm)λmax:454nm

[0709] Compound 6

[0710]

[0711] The synthetic procedure of compound 1 was repeated except that dibenzo[b,d]furan-4-ylboronic acid was used instead of dibenzo[b,d]furan-3-ylboronic acid. Compound 6 (62% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry), maximum ultraviolet absorption wavelength in toluene (UV(PhMe)λonset) and maximum fluorescence wavelength in toluene (FL(PhMe,λex=330nm)λmax). The results are shown below.

[0712] ESI-MS: Calculated value for C55H53BN2O = 768, found mass = 769 (M+1)

[0713] UV(PhMe)λonset:458nm

[0714] FL(PhMe,λex=400nm)λmax:455nm

[0715] Compound 7

[0716]

[0717] The synthetic procedure of compound 1 was repeated except that dibenzo[b,d]thiophene-4-ylboronic acid was used instead of dibenzo[b,d]furan-3-ylboronic acid. Compound 7 (82% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry), maximum ultraviolet absorption wavelength in toluene (UV(PhMe)λonset) and maximum fluorescence wavelength in toluene (FL(PhMe,λex=330nm)λmax). The results are shown below.

[0718] ESI-MS: Calculated value for C55H53BN2S = 784, found mass = 785 (M+1)

[0719] UV(PhMe)λonset:458nm

[0720] FL(PhMe,λex=400nm)λmax:454nm

[0721] Compound 8

[0722]

[0723] 4-Chloroaniline (10.5 g, 82 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (20 g, 75 mmol) were combined in toluene (250 ml) in a 500 ml 3-necked round bottom flask and degassed with nitrogen. Tris(dibenzylideneacetone)dipalladium(0) (0.68 g, 0.75 mmol), 9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) (1.7 g, 3 mmol) and sodium tert-butoxide (10 g, 105 mmol) were then added. The reaction mixture was heated at an oil bath temperature of 120° C. for 2 hours. The reaction mixture was then cooled to room temperature and the insoluble precipitate was removed by filtration through a celite pad. The mother liquor was then washed successively with a 2M aqueous hydrogen chloride solution, water, and then with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered through a silica pad, rinsing with toluene. The solvent was evaporated under reduced pressure, and the crude residue was dissolved in hot 2-propanol. The fine precipitate formed was removed by filtration and discarded. The solvent was evaporated under reduced pressure, and intermediate 13 was purified by recrystallization from hexane. Intermediate 13 (17 grams, 72.4% yield) was isolated as a white solid, which was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0724] ESI-MS: calculated value for C20H24ClN = 313, found mass = 314 (M+1)

[0725]

[0726] 1,2-Dibromo-3-iodo-5-methylbenzene (7.4 g, 19.6 mmol), intermediate 13 (12.3 g, 39.2 mmol), bis(tri-tert-butylphosphine)palladium (0.4 g, 0.78 mmol) and sodium tert-butoxide (5.3 g, 54.9 mmol) were added to a degassed 500 ml three-necked round bottom flask. Toluene (200 ml) was added and the reaction mixture was heated at an oil bath temperature of 115°C for 3 hours. The reaction was cooled to room temperature and filtered through a celite pad and washed with toluene. The mother liquor was then washed successively with saturated aqueous sodium bicarbonate solution, water, and finally with saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4 and the solvent was evaporated. The crude product was recrystallized from 2-propanol. Intermediate 14 (10.5 g, 67.4% yield) was thus isolated and characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0727] ESI-MS: calculated value for C47H51BrCl2N2 = 792, found mass = 793 (M+1).

[0728]

[0729] Intermediate 14 (9.5 g, 11.9 mmol) was dissolved in tert-butylbenzene (200 ml) and cooled in a 0°C water-ice bath under N2. Sec-butyl lithium (1.4M cyclohexane solution, 12.8 ml, 17.9 mmol) was added dropwise via a syringe, and the resulting reaction mixture was allowed to warm to room temperature. After 2 hours, the lithiation of intermediate 14 was completed. The reaction mixture was cooled at -30°C, and then boron tribromide (1M heptane solution, 17.9 ml, 17.9 mmol) was added dropwise. After the addition was complete, the reaction was allowed to warm to room temperature. The reaction was then heated at an oil bath temperature of 140°C for 2 hours. The reaction was cooled to room temperature, then diisopropylethylamine (4.2 ml, 23.9 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The reaction was then quenched by adding 10% sodium acetate aqueous solution, and toluene was added to dissolve any residual precipitate. The organic phase was separated and washed successively with saturated sodium bicarbonate aqueous solution, water, then with saturated sodium chloride aqueous solution, and dried over magnesium sulfate. The solvent was concentrated to 50 milliliters under reduced pressure and the crude product was precipitated with ethanol. Purification can be achieved by recrystallization from a xylene-2-propanol mixture. Intermediate 15 (3.2 grams, 37% yield) was isolated as a yellow solid and characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0730] ESI-MS: calculated value for C47H49BCl2N2 = 722, found mass = 723 (M+1)

[0731]

[0732] Into a 250 ml degassed 3-necked round bottom flask was added intermediate 15 (3.2 g, 4.46 mmol), dibenzo[b,d]furan-4-ylboronic acid (3.8 g, 17.8 mmol), palladium(II) acetate (0.1 g, 0.44 mmol), [2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl] (0.43 g, 0.89 mmol) and cesium carbonate (5.82, 17.8 mmol), followed by toluene (80 ml), ethanol (15 ml) and water (15 ml). The resulting reaction mixture was heated overnight at an oil bath temperature of 100°C under a nitrogen atmosphere. The reaction mixture was then cooled to room temperature and diluted with ethanol (50 ml). Insoluble material was collected by filtration. The filter cake was then dissolved with dichloromethane and filtered through a silica pad, rinsed with dichloromethane. The solvent was then evaporated to obtain the desired compound. The obtained compound 8 (84%) was characterized by ESI-MS (electrospray ionization mass spectrometry), maximum ultraviolet absorption wavelength in toluene (UV (PhMe) λonset) and maximum fluorescence wavelength in toluene (FL (PhMe, λex = 330 nm) λmax). The results are shown below.

[0733] ESI-MS: Calculated value for C71H63BN2O2 = 986, found mass = 987 (M+1)

[0734] UV(PhMe)λonset:457nm

[0735] FL(PhMe,λex=400nm)λmax:456nm

[0736] Compound 9

[0737]

[0738] The synthetic procedure of compound 8 was repeated except that intermediate 5 was used instead of intermediate 15 and 2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of dibenzo[b,d]furan-4-ylboronic acid. The obtained compound 9 (97%) was characterized by ESI-MS (electrospray ionization mass spectrometry), maximum ultraviolet absorption wavelength in toluene (UV(PhMe)λonset) and maximum fluorescence wavelength in toluene (FL(PhMe,λex=330nm)λmax). The results are shown below.

[0739] ESI-MS: Calculated value for C63H51BN2O2 = 878, found mass = 879 (M+1)

[0740] UV(PhMe)λonset:447nm

[0741] FL(PhMe,λex=400nm)λmax:445nm

[0742] Compound 10

[0743]

[0744] The synthetic procedure of compound 8 was repeated, except that intermediate 5 was used instead of intermediate 15 and 2-(9,9-dimethyl-9H-fluorene-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of dibenzo[b,d]furan-4-ylboronic acid. The obtained compound 10 (88%) was characterized by ESI-MS (electrospray ionization mass spectrometry), maximum ultraviolet absorption wavelength in toluene (UV(PhMe)λonset) and maximum fluorescence wavelength in toluene (FL(PhMe,λex=330nm)λmax). The results are shown below.

[0745] ESI-MS: Calculated value for C69H63BN2 = 931, found mass = 932 (M+1)

[0746] UV(PhMe)λonset:446nm

[0747] FL(PhMe,λex=400nm)λmax:445nm

[0748] Compound 11

[0749]

[0750] The synthetic procedure of intermediate 14 was repeated except that 1,2-dibromo-5-(tert-butyl)-3-iodobenzene was used instead of 1,2-dibromo-3-iodo-5-methylbenzene and N-(4-chlorophenyl)aniline was used instead of intermediate 13. The obtained intermediate 16 (71% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0751] ESI-MS: calculated value for C42H45BrCl2N2 = 726, found mass = 727 (M+1).

[0752]

[0753] The synthetic procedure of intermediate 15 was repeated except that intermediate 16 was used instead of intermediate 14 and n-butyl lithium was used instead of sec-butyl lithium. The obtained intermediate 17 (33% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0754] ESI-MS: calculated value for C42H43BCl2N2 = 656, found mass = 657 (M+1)

[0755]

[0756] The synthetic procedure of compound 8 was repeated, except that intermediate 17 was used instead of intermediate 15. The obtained compound 11 (95%) was characterized by ESI-MS (electrospray ionization mass spectrometry), the maximum ultraviolet absorption wavelength in toluene (UV (PhMe) λonset) and the maximum fluorescence wavelength in toluene (FL (PhMe, λex = 330 nm) λmax). The results are shown below.

[0757] ESI-MS: Calculated value for C66H57BN2O2 = 920, found mass = 921 (M+1)

[0758] UV(PhMe)λonset:454nm

[0759] FL(PhMe,λex=400nm)λmax:449nm

[0760] Compound 12

[0761]

[0762] The synthetic procedure of compound 8 was repeated except that intermediate 17 was used instead of intermediate 15 and 2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of dibenzo[b,d]furan-4-ylboronic acid. The obtained compound 12 (82%) was characterized by ESI-MS (electrospray ionization mass spectrometry), maximum ultraviolet absorption wavelength in toluene (UV(PhMe)λonset) and maximum fluorescence wavelength in toluene (FL(PhMe,λex=330nm)λmax). The results are shown below.

[0763] ESI-MS: Calculated value for C66H57BN2O2 = 920, found mass = 921 (M+1)

[0764] UV(PhMe)λonset:454nm

[0765] FL(PhMe,λex=400nm)λmax:449nm

[0766] Compound 13

[0767]

[0768] The synthetic procedure of compound 8 was repeated, except that intermediate 17 was used instead of intermediate 15 and 2-(9,9-dimethyl-9H-fluorene-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of dibenzo[b,d]furan-4-ylboronic acid. The obtained compound 13 (82%) was characterized by ESI-MS (electrospray ionization mass spectrometry), maximum ultraviolet absorption wavelength in toluene (UV(PhMe)λonset) and maximum fluorescence wavelength in toluene (FL(PhMe,λex=330nm)λmax). The results are shown below.

[0769] ESI-MS: Calculated value for C72H69BN2 = 973, found mass = 974 (M+1)

[0770] UV(PhMe)λonset:453nm

[0771] FL(PhMe,λex=400nm)λmax:449nm

[0772] Compound 14

[0773]

[0774] The synthetic procedure of intermediate 13 was repeated except that 2-bromo-4-(tert-butyl)aniline was used instead of 4-chloroaniline and 1-chloro-4-iodobenzene was used instead of 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene. The obtained intermediate 18 (82%) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0775] ESI-MS: calculated value for C16H17BrClN = 337, found mass = 338 (M+1)

[0776]

[0777] Trifluoroacetic acid (46.3 ml, 601 mmol), dichloromethane (30 ml) and 1-bromo-4-(tert-butyl)benzene (16.27 ml, 94 mmol) were added to a 250 ml 3-necked round-bottom flask. The reaction mixture was cooled in a water-ice bath and N-iodosuccinimide (25.3 g, 113 mmol) was added in portions. After N-iodosuccinimide was added completely, the ice-water bath was removed and the reaction was continued at room temperature for 6 hours. The reaction was then cooled again in a water-ice bath, N-iodosuccinimide (16.9 g, 75 mmol) was added in portions to the reaction, trifluoromethanesulfonic acid (12.5 ml, 141 mmol) was then added, and the reaction was continued overnight to slowly warm to room temperature. Another portion of N-iodosuccinimide (2.5 g, 11.1 mmol) was added and the reaction was continued for another 4 hours. The reaction mixture was then quenched by slowly pouring onto an ice-cold 30% aqueous sodium hydroxide solution while stirring. A 10% aqueous sodium thiosulfate solution (250 ml) was then added. The crude product was then extracted with dichloromethane. The solvent was evaporated and the crude product was recrystallized from an ethyl acetate-methanol mixture. Intermediate 19 (38.4 g, 88%) was characterized by 1H NMR (270 MHz, CD2Cl2) 7.90 ppm (2H, s); 1.30 ppm (9H, s).

[0778]

[0779] The synthetic procedure of intermediate 1 was repeated except that intermediate 19 was used instead of 1,2-dibromo-3-iodo-5-methylbenzene, intermediate 18 was used instead of bis(4-(tert-butyl)phenyl)amine and xylene was used instead of toluene. The obtained intermediate 20 (63% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0780] ESI-MS: calculated value for C26H27Br2ClIN = 673, found mass = 674 (M+1)

[0781]

[0782] The synthetic procedure of intermediate 1 was repeated except that intermediate 20 was used instead of 1,2-dibromo-3-iodo-5-methylbenzene, intermediate 18 was used instead of bis(4-(tert-butyl)phenyl)amine and xylene was used instead of toluene. The obtained intermediate 21 (44% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0783] ESI-MS: Calculated value for C42H43Br3Cl2N2 = 882, found mass = 883 (M+1)

[0784]

[0785] In 100 ml 3-necked round-bottom flask under nitrogen, intermediate 21 (4.9 g, 5.6 mmol) was dissolved in tert-butylbenzene (50 ml) and cooled to <10 ° C in a water-ice bath. Sec-butyl lithium (12 ml, 16.8 mmol, 1.4M in cyclohexane) was added, the reaction mixture was allowed to warm to room temperature and continued for 1 hour. Then the reaction was cooled to 0 ° C in a water-ice bath and trimethoxyborane (2.86 ml, 25.2 mmol) was slowly added. After the addition was completed, the reaction was allowed to warm to room temperature, then heated at 100 ° C oil bath temperature, and continued at this temperature for 4 hours. Then the reaction was cooled to room temperature. The precipitate formed was collected by filtration, and water, then washed with ethanol. Purification by recrystallization from toluene, to isolate intermediate 22 (2.95 g, 80%) as a yellow solid, and characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0786] ESI-MS: calculated value for C42H43BCl2N2 = 656, found mass = 657 (M+1)

[0787]

[0788] The synthetic procedure of compound 8 was repeated, except that intermediate 22 was used instead of intermediate 15. The obtained compound 14 (88%) was characterized by ESI-MS (electrospray ionization mass spectrometry), the maximum ultraviolet absorption wavelength in toluene (UV (PhMe) λonset) and the maximum fluorescence wavelength in toluene (FL (PhMe, λex = 330 nm) λmax). The results are shown below.

[0789] ESI-MS: Calculated value for C66H57BN2O2 = 920, found mass = 921 (M+1)

[0790] UV(PhMe)λonset:462nm

[0791] FL(PhMe,λex=400nm)λmax:458nm

[0792] Compound 15

[0793]

[0794] The synthetic procedure of compound 8 was repeated, except that intermediate 22 was used instead of intermediate 15 and 2-(9,9-dimethyl-9H-fluorene-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of dibenzo[b,d]furan-4-ylboronic acid. The obtained compound 15 (97%) was characterized by ESI-MS (electrospray ionization mass spectrometry), maximum ultraviolet absorption wavelength in toluene (UV(PhMe)λonset) and maximum fluorescence wavelength in toluene (FL(PhMe,λex=330nm)λmax). The results are shown below.

[0795] ESI-MS: Calculated value for C72H69BN2 = 973, found mass = 973 (M)

[0796] UV(PhMe)λonset:461nm

[0797] FL(PhMe,λex=400nm)λmax:458nm

[0798] Compound 16

[0799]

[0800] The synthetic procedure of Intermediate 1 was repeated except that Intermediate 1 was used instead of 1,2-dibromo-3-iodo-5-methylbenzene, Intermediate 13 was used instead of bis(4-(tert-butyl)phenyl)amine and bis(tri-tert-butylphosphanyl)palladium was used instead of tris(dibenzylideneacetone)dipalladium(0) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane). The obtained Intermediate 23 (60% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0801] ESI-MS: calculated value for C47H54BrClN2 = 762, found mass = 763 (M+1)

[0802]

[0803] The synthetic procedure of intermediate 15 was repeated except that intermediate 23 was used instead of intermediate 14. The obtained intermediate 24 (18% yield) was characterized by ESI-MS (electrospray ionization). The results are shown below.

[0804] ESI-MS: Calculated value for C47H52BClN2 = 691, found mass = 692 (M+1)

[0805]

[0806] The synthetic procedure of compound 1 was repeated, except that intermediate 24 was used instead of intermediate 3 and dibenzo[b,d]furan-4-ylboronic acid was used instead of dibenzo[b,d]furan-3-ylboronic acid. Compound 16 (94% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry), maximum ultraviolet absorption wavelength in toluene (UV(PhMe)λonset) and maximum fluorescence wavelength in toluene (FL(PhMe,λex=330nm)λmax). The results are shown below.

[0807] ESI-MS: Calculated value for C59H59BN2O = 823, found mass = 724 (M+1)

[0808] UV(PhMe)λonset:459nm

[0809] FL(PhMe,λex=400nm)λmax:455nm

[0810] Compound 17

[0811]

[0812] The synthetic procedure of Intermediate 1 was repeated except that 3-(tert-butyl)-N-(4-chlorophenyl)aniline was used instead of bis(4-(tert-butyl)phenyl)amine. The obtained Intermediate 25 (69% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0813] ESI-MS: calculated value for C23H22Br2ClN = 508, found mass = 509 (M+1)

[0814]

[0815] The synthetic procedure of Intermediate 1 was repeated except that Intermediate 25 was used instead of 1,2-dibromo-3-iodo-5-methylbenzene, 5-(tert-butyl)-N-(4-(tert-butyl)phenyl)-[1,1'-biphenyl]-2-amine was used instead of bis(4-(tert-butyl)phenyl)amine and bis(tri-tert-butylphosphanyl)palladium was used instead of tris(dibenzylideneacetone)dipalladium(0) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane). The obtained Intermediate 26 (46% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0816] ESI-MS: Calculated value for C49H52BrClN2 = 784, found mass = 785 (M+1)

[0817]

[0818] The synthetic procedure of Intermediate 15 was repeated except that Intermediate 26 was used instead of Intermediate 14. The obtained Intermediate 27 (19% yield) was characterized by ESI-MS (electrospray pressure chemical ionization). The results are shown below.

[0819] ESI-MS: Calculated value for C47H52BClN2 = 691, found mass = 692 (M+1)

[0820]

[0821] The synthetic procedure of compound 1 was repeated except that intermediate 27 was used instead of intermediate 3 and dibenzo[b,d]furan-4-ylboronic acid was used instead of dibenzo[b,d]furan-3-ylboronic acid. Compound 17 (82% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry), maximum ultraviolet absorption wavelength in toluene (UV(PhMe)λonset) and maximum fluorescence wavelength in toluene (FL(PhMe,λex=330nm)λmax). The results are shown below.

[0822] ESI-MS: Calculated value for C61H57BN2O = 845, found mass = 846 (M+1)

[0823] UV(PhMe)λonset:457nm

[0824] FL(PhMe,λex=400nm)λmax:456nm

[0825] Compound 18

[0826]

[0827] The synthetic procedure of intermediate 1 was repeated except that 3-(tert-butyl)-N-(4-chlorophenyl)aniline was used instead of bis(4-(tert-butyl)phenyl)amine and 1,2-dibromo-5-(tert-butyl)-3-iodobenzene was used instead of 1,2-dibromo-3-iodo-5-methylbenzene. The obtained intermediate 28 (62% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0828] ESI-MS: Calculated value for C26H28Br2ClN = 550, found mass = 550 (M+)

[0829]

[0830] The synthetic procedure of Intermediate 1 was repeated except that Intermediate 28 was used instead of 1,2-dibromo-3-iodo-5-methylbenzene, 4-(tert-butyl)-N-(4-chlorophenyl)aniline was used instead of bis(4-(tert-butyl)phenyl)amine and bis(tri-tert-butylphosphanyl)palladium was used instead of tris(dibenzylideneacetone)dipalladium(0) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane). The obtained Intermediate 29 (60% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0831] ESI-MS: Calculated value for C42H45BrCl2N2 = 729, found mass = 729 (M+)

[0832]

[0833] The synthetic procedure of intermediate 15 was repeated except that intermediate 29 was used instead of intermediate 14. The obtained intermediate 30 (30% yield) was characterized by ESI-MS (electrospray ionization). The results are shown below.

[0834] ESI-MS: calculated value for C42H43BCl2N2 = 657, found mass = 658 (M+1)

[0835]

[0836] The synthetic procedure of compound 8 was repeated, except that intermediate 30 was used instead of intermediate 15. Compound 18 (82% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry), maximum ultraviolet absorption wavelength in toluene (UV (PhMe) λonset) and maximum fluorescence wavelength in toluene (FL (PhMe, λex = 330 nm) λmax). The results are shown below.

[0837] ESI-MS: Calculated value for C66H57BN2O2 = 921, found mass = 922 (M+1)

[0838] UV(PhMe)λonset:456nm

[0839] FL(PhMe,λex=400nm)λmax:454nm

[0840] Compound 19

[0841]

[0842] The synthetic procedure of intermediate 14 was repeated except that 1,2-dibromo-5-(tert-butyl)-3-iodobenzene was used instead of 1,2-dibromo-3-iodo-5-methylbenzene and 3-(tert-butyl)-N-(3-chlorophenyl)aniline was used instead of intermediate 13. The obtained intermediate 31 (81% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0843] ESI-MS: calculated value for C42H45BrCl2N2 = 728, found mass = 729 (M+1).

[0844]

[0845] The synthetic procedure of intermediate 15 was repeated except that intermediate 31 was used instead of intermediate 14 and n-butyl lithium was used instead of sec-butyl lithium. The obtained intermediate 32 (21% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0846] ESI-MS: Calculated value for C42H43BCl2N2 = 657, found mass = 657 (M+)

[0847]

[0848] The synthetic procedure of compound 8 was repeated, except that intermediate 32 was used instead of intermediate 15. The obtained compound 19 (85%) was characterized by ESI-MS (electrospray ionization mass spectrometry), the maximum ultraviolet absorption wavelength in toluene (UV (PhMe) λonset) and the maximum fluorescence wavelength in toluene (FL (PhMe, λex = 330nm) λmax). The results are shown below.

[0849] ESI-MS: Calculated value for C66H57BN2O2 = 920, found mass = 921 (M+1)

[0850] UV(PhMe)λonset:451nm

[0851] FL(PhMe,λex=400nm)λmax:449nm

[0852] Compound 20

[0853]

[0854] The synthetic procedure of intermediate 13 was repeated except that 5-bromo-2-chloro-1,3-dimethylbenzene was used instead of 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene and 3-(tert-butyl)aniline was used instead of 4-chloroaniline. The obtained intermediate 33 (93% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0855] ESI-MS: calculated value for C18H22ClN = 288, found mass = 289 (M+1).

[0856]

[0857] The synthetic procedure of intermediate 14 was repeated except that 2-bromo-1,3-diiodo-5-methylbenzene was used instead of 1,2-dibromo-3-iodo-5-methylbenzene and intermediate 33 was used instead of intermediate 13. The obtained intermediate 34 (64% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0858] ESI-MS: calculated value for C43H47BrCl2N2 = 743, found mass = 743 (M+).

[0859]

[0860] The synthetic procedure of intermediate 15 was repeated except that intermediate 34 was used instead of intermediate 14. The obtained intermediate 35 (18% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0861] ESI-MS: calculated value for C43H45BCl2N2 = 670, found mass = 671 (M+1)

[0862]

[0863] The synthetic procedure of compound 8 was repeated, except that intermediate 35 was used instead of intermediate 15 and dibenzo[b,d]furan-3-ylboronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid. The obtained compound 20 (70%) was characterized by ESI-MS (electrospray ionization mass spectrometry), maximum ultraviolet absorption wavelength in toluene (UV(PhMe)λonset) and maximum fluorescence wavelength in toluene (FL(PhMe,λex=330nm)λmax). The results are shown below.

[0864] ESI-MS: Calculated value for C67H59BN2O2 = 935, found mass = 936 (M+1)

[0865] UV(PhMe)λonset:450nm

[0866] FL(PhMe,λex=400nm)λmax:447nm

[0867] (UV(PhMe)λonset) in toluene and maximum fluorescence wavelength in toluene (FL(PhMe,λex=330nm)λmax). The results are shown below.

[0868] ESI-MS: Calculated value for C70H65BN2O2 = 977, found mass = 978 (M+1)

[0869] UV(PhMe)λonset:450nm

[0870] FL(PhMe,λex=400nm)λmax:446nm

[0871] Compound 21

[0872]

[0873] The synthetic procedure of Intermediate 1 was repeated except that 3-(tert-butyl)-N-(4-chlorophenyl)aniline was used instead of bis(4-(tert-butyl)phenyl)amine. The obtained Intermediate 36 (92% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0874] ESI-MS: Calculated value for C23H22Br2ClN = 507, found mass = 507 (M+)

[0875]

[0876] The synthetic procedure of intermediate 13 was repeated except that 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine was used instead of 4-chloroaniline, intermediate 36 was used instead of 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene and (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) was used instead of 9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane). The obtained intermediate 37 (54% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0877] ESI-MS: calculated value for C37H42BrClN2 = 630, found mass = 631 (M+1).

[0878]

[0879] The synthetic procedure of intermediate 1 was repeated except that intermediate 37 was used instead of bis(4-(tert-butyl)phenyl)amine and 1-bromo-4-(tert-butyl)-2-iodobenzene was used instead of 1,2-dibromo-3-iodo-5-methylbenzene. The obtained intermediate 38 (65% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0880] ESI-MS: Calculated value for C47H53Br2ClN2 = 841, found mass = 841 (M+)

[0881]

[0882] Intermediate 38 (6.3 g, 7.26 mmol) is dissolved in tert-butylbenzene and degassed under nitrogen. The solution is cooled to -15 ° C in a salt-ice bath, and tert-butyl lithium (15.3 liters, 29.1 mmol, 1.7M in hexane) is added. After the addition is completed, the reaction is warmed to room temperature for 1.5 hours. Then trimethoxyborane (2.4 ml, 21.8 mmol) is added and the reaction is continued at room temperature. After 2 hours, the reaction is cooled at -65 ° C in an acetone-dry ice bath. Then boron tribromide (4.1 ml, 43.6 mmol) is added and the reaction is continued overnight to slowly rise to room temperature. Then diisopropylethylamine (11.4 ml, 65.4 mmol) is added and the reaction is continued for another 4 hours. The reaction is then diluted with ethanol (300 ml), and a yellow solid (1.1 g, 21.9% yield) is collected by filtration and used without further purification. The obtained intermediate 39 was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0883] ESI-MS: Calculated value for C47H52BClN2 = 691, found mass = 692 (M+1)

[0884]

[0885] The synthetic procedure of compound 1 was repeated, except that intermediate 39 was used instead of intermediate 3 and dibenzo[b,d]furan-4-ylboronic acid was used instead of dibenzo[b,d]furan-3-ylboronic acid. The obtained compound 21 (31%) was characterized by ESI-MS (electrospray ionization mass spectrometry), the maximum ultraviolet absorption wavelength in toluene (UV(PhMe)λonset) and the maximum fluorescence wavelength in toluene (FL(PhMe,λex=330nm)λmax). The results are shown below.

[0886] ESI-MS: Calculated value for C59H59BN2O = 823, found mass = 824 (M+1)

[0887] UV(PhMe)λonset:450nm

[0888] FL(PhMe,λex=400nm)λmax:447nm

[0889] Compound 22

[0890]

[0891] The synthetic procedure of Intermediate 1 was repeated except that Intermediate 28 was used instead of 1,2-dibromo-3-iodo-5-methylbenzene, Intermediate 13 was used instead of bis(4-(tert-butyl)phenyl)amine and bis(tri-tert-butylphosphanyl)palladium was used instead of tris(dibenzylideneacetone)dipalladium(0) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane). The obtained Intermediate 40 (78% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0892] ESI-MS: Calculated value for C46H51BrCl2N2 = 782, found mass = 793 (M+1)

[0893]

[0894] The synthetic procedure of Intermediate 15 was repeated except that Intermediate 40 was used instead of Intermediate 14. The obtained Intermediate 41 (29% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0895] ESI-MS: Calculated value for C46H49BCl2N2 = 711, found mass = 711 (M+1)

[0896]

[0897] The synthetic procedure of compound 8 was repeated, except that intermediate 41 was used instead of intermediate 15. The obtained compound 22 (91%) was characterized by ESI-MS (electrospray ionization mass spectrometry), the maximum ultraviolet absorption wavelength in toluene (UV (PhMe) λonset) and the maximum fluorescence wavelength in toluene (FL (PhMe, λex = 330 nm) λmax). The results are shown below.

[0898] ESI-MS: Calculated value for C70H63BN2O2 = 975, found mass = 975 (M+)

[0899] UV(PhMe)λonset:456nm

[0900] FL(PhMe,λex=400nm)λmax:457nm

[0901] Compound 23

[0902]

[0903] The synthetic procedure of intermediate 14 was repeated except that 1,2-dibromo-3-iodobenzene was used instead of 1,2-dibromo-3-iodo-5-methylbenzene and 3-(tert-butyl)-N-(4-chlorophenyl)aniline was used instead of intermediate 13. The obtained intermediate 42 (82% yield) was characterized by ESI-MS (electrospray ionization). The results are shown below.

[0904] ESI-MS: calculated value for C38H37BrCl2N2 = 672, found mass = 673 (M+1).

[0905]

[0906] The synthetic procedure of intermediate 15 was repeated except that intermediate 42 was used instead of intermediate 14. The obtained intermediate 43 (35% yield) was characterized by ESI-MS (electrospray ionization). The results are shown below.

[0907] ESI-MS: calculated value for C38H35BCl2N2 = 601, found mass = 602 (M+1)

[0908]

[0909] The synthetic procedure of compound 8 was repeated, except that intermediate 43 was used instead of intermediate 15. The obtained compound 23 (97%) was characterized by ESI-MS (electrospray ionization mass spectrometry), the maximum ultraviolet absorption wavelength in toluene (UV (PhMe) λonset) and the maximum fluorescence wavelength in toluene (FL (PhMe, λex = 330 nm) λmax). The results are shown below.

[0910] ESI-MS: Calculated value for C62H49BN2O2 = 865, found mass = 866 (M+1)

[0911] UV(PhMe)λonset:452nm

[0912] FL(PhMe,λex=400nm)λmax:448nm

[0913] Compound 24

[0914]

[0915] The synthetic procedure of intermediate 1 was repeated except that 3-(tert-butyl)-N-(4-chlorophenyl)aniline was used instead of bis(4-(tert-butyl)phenyl)amine and 1,2-dibromo-3-iodobenzene was used instead of 1,2-dibromo-3-iodo-5-methylbenzene. The obtained intermediate 44 (91% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0916] ESI-MS: Calculated value for C22H20Br2ClN = 494, found mass = 494 (M+)

[0917]

[0918] The synthetic procedure of Intermediate 1 was repeated except that Intermediate 44 was used instead of 1,2-dibromo-3-iodo-5-methylbenzene, 4-(tert-butyl)-N-(4-chlorophenyl)aniline was used instead of bis(4-(tert-butyl)phenyl)amine and bis(tri-tert-butylphosphanyl)palladium was used instead of tris(dibenzylideneacetone)dipalladium(0) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane). The obtained Intermediate 45 (72% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0919] ESI-MS: Calculated value for C38H37BrCl2N2 = 672, found mass = 672 (M+)

[0920]

[0921] The synthetic procedure of intermediate 15 was repeated except that intermediate 45 was used instead of intermediate 14. The obtained intermediate 46 (35% yield) was characterized by ESI-MS (electrospray ionization). The results are shown below.

[0922] ESI-MS: calculated value for C38H35BCl2N2 = 601, found mass = 602 (M+1)

[0923]

[0924] The synthetic procedure of compound 8 was repeated, except that intermediate 46 was used instead of intermediate 15. Compound 24 (96% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry), maximum ultraviolet absorption wavelength in toluene (UV (PhMe) λonset) and maximum fluorescence wavelength in toluene (FL (PhMe, λex = 330 nm) λmax). The results are shown below.

[0925] ESI-MS: Calculated value for C62H49BN2O2 = 865, found mass = 866 (M+1)

[0926] UV(PhMe)λonset:452nm

[0927] FL(PhMe,λex=400nm)λmax:448nm

[0928] Compound 25

[0929]

[0930] The synthetic procedure of intermediate 1 was repeated except that 4-(dibenzo[b,d]furan-4-yl)aniline was used instead of bis(4-(tert-butyl)phenyl)amine, 1-bromo-4-(tert-butyl)-2-iodobenzene was used instead of 1,2-dibromo-3-iodo-5-methylbenzene, and (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) was used instead of (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane). The obtained intermediate 47 (97% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0931] ESI-MS: calculated value for C28H24BrNO=469, found mass=470 (M+1).

[0932]

[0933] The synthetic procedure of intermediate 1 was repeated except that intermediate 47 was used instead of bis(4-(tert-butyl)phenyl)amine and 1,2-dibromo-5-(tert-butyl)-3-iodobenzene was used instead of 1,2-dibromo-3-iodo-5-methylbenzene. The obtained intermediate 48 (94% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0934] ESI-MS: calculated value for C38H34Br3NO=757, found mass=758 (M+1).

[0935]

[0936] The synthetic procedure of Intermediate 1 was repeated except that 9,9-dimethyl-9H-fluorene-2-amine was used instead of bis(4-(tert-butyl)phenyl)amine, Intermediate 48 was used instead of 1,2-dibromo-3-iodo-5-methylbenzene, and (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) was used instead of (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane). The obtained Intermediate 49 (73% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0937] ESI-MS: calculated value for C53H48Br2N2O = 886, found mass = 887 (M+1).

[0938]

[0939] The synthetic procedure of intermediate 1 was repeated except that intermediate 49 was used instead of bis(4-(tert-butyl)phenyl)amine and 1-bromo-4-(tert-butyl)-2-iodobenzene was used instead of 1,2-dibromo-3-iodo-5-methylbenzene. The obtained intermediate 50 (89% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0940] ESI-MS: calculated value for C53H48Br2N2O = 1074, found mass = 1075 (M+1).

[0941]

[0942] The synthetic procedure of intermediate 22 was repeated except that intermediate 50 was used instead of intermediate 21. Compound 25 (72% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry), maximum ultraviolet absorption wavelength in toluene (UV (PhMe) λonset) and maximum fluorescence wavelength in toluene (FL (PhMe, λex = 330 nm) λmax). The results are shown below.

[0943] ESI-MS: Calculated value for C63H59BN2O = 871, found mass = 872 (M+1)

[0944] UV(PhMe)λonset:454nm

[0945] FL(PhMe,λex=400nm)λmax:451nm

[0946] Compound 26

[0947]

[0948] The synthetic procedure of Intermediate 1 was repeated except that Intermediate 44 was used instead of 1,2-dibromo-3-iodo-5-methylbenzene, N-(4-(tert-butyl)phenyl)-[1,1':3',1"-terphenyl]-4'-amine was used instead of bis(4-(tert-butyl)phenyl)amine and bis(tri-tert-butylphosphanyl)palladium was used instead of tris(dibenzylideneacetone)dipalladium(0) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane). The obtained Intermediate 51 (72% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0949] ESI-MS: Calculated value for C50H46BrClN2 = 788, found mass = 788 (M+)

[0950]

[0951] The synthetic procedure of Intermediate 15 was repeated except that Intermediate 51 was used instead of Intermediate 14. The obtained Intermediate 52 (33% yield) was characterized by ESI-MS (electrospray ionization). The results are shown below.

[0952] ESI-MS: calculated value for C50H44BClN2 = 718, found mass = 719 (M+1)

[0953]

[0954] The synthetic procedure of compound 1 was repeated except that intermediate 52 was used instead of intermediate 3 and dibenzo[b,d]furan-4-ylboronic acid was used instead of dibenzo[b,d]furan-3-ylboronic acid. Compound 26 (92% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry), maximum ultraviolet absorption wavelength in toluene (UV(PhMe)λonset) and maximum fluorescence wavelength in toluene (FL(PhMe,λex=330nm)λmax). The results are shown below.

[0955] ESI-MS: Calculated value for C58H43BN2O = 794, found mass = 795 (M+1)

[0956] UV(PhMe)λonset:457nm

[0957] FL(PhMe,λex=400nm)λmax:454nm

[0958] Comparative Compound 2

[0959]

[0960] The synthetic procedure of intermediate 1 was repeated except that diphenylamine was used instead of bis(4-(tert-butyl)phenyl)amine and 1,2-dibromo-3-iodobenzene was used instead of 1,2-dibromo-3-iodo-5-methylbenzene. The obtained intermediate 53 (49% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0961] ESI-MS: Calculated value for C18H13Br2N = 403, found mass = 403 (M+)

[0962]

[0963] The synthetic procedure of Intermediate 1 was repeated except that Intermediate 53 was used instead of 1,2-dibromo-3-iodo-5-methylbenzene, 4-chloro-N-phenylaniline was used instead of bis(4-(tert-butyl)phenyl)amine and bis(tri-tert-butylphosphanyl)palladium was used instead of tris(dibenzylideneacetone)dipalladium(0) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane). The obtained Intermediate 54 (55% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry). The results are shown below.

[0964] ESI-MS: Calculated value for C30H22BrClN2 = 526, found mass = 526 (M+)

[0965]

[0966] The synthetic procedure of Intermediate 3 was repeated except that Intermediate 54 was used instead of Intermediate 2 and sec-butyl lithium was used instead of tert-butyl lithium. The obtained Intermediate 55 (20% yield) was characterized by ESI-MS (electrospray ionization). The results are shown below.

[0967] ESI-MS: calculated value for C30H20BClN2 = 455, found mass = 456 (M+1)

[0968]

[0969] The synthetic procedure of compound 1 was repeated, except that intermediate 55 was used instead of intermediate 3 and dibenzo[b,d]furan-4-ylboronic acid was used instead of dibenzo[b,d]furan-3-ylboronic acid. Comparative compound 2 (81% yield) was characterized by ESI-MS (electrospray ionization mass spectrometry), maximum ultraviolet absorption wavelength in toluene (UV(PhMe)λonset) and maximum fluorescence wavelength in toluene (FL(PhMe,λex=330nm)λmax). The results are shown below.

[0970] ESI-MS: Calculated value for C42H27BN2O = 586, found mass = 587 (M+1)

[0971] UV(PhMe)λonset:457nm

[0972] FL(PhMe,λex=400nm)λmax:452nm

[0973] Devices (compounds of the invention as emitters / dopants)

[0974] Preparation and evaluation of organic EL devices

[0975] Organic EL devices were prepared and evaluated as follows:

[0976] Application Example 1

[0977] A glass substrate with a 130 nm thick indium tin oxide (ITO) transparent electrode (manufactured by Geomatec Co., Ltd.) used as an anode was first treated with N2 plasma for 100 seconds. This treatment also improves the hole injection properties of ITO. The cleaned substrate was mounted on a substrate holder and loaded into a vacuum chamber. Thereafter, the organic materials specified below were added at about 10 -6 -10 -8 mbar below about The rate is applied to the ITO substrate by vapor deposition. As a hole injection layer, a mixture of 10nm thick compound HT-1 and 3 wt% compound HI is applied. Then 80nm thick compound HT-1 and 10nm compound HT-2 are applied as hole transport layer 1 and hole transport layer 2, respectively. Subsequently, a mixture of 2 wt% emitter compound 1 and 98 wt% host compound BH-1 is applied to form a 25nm thick fluorescent emission layer. On this emission layer, 10nm thick compound ET-1 is applied as a hole blocking layer, and 15nm compound ET-2 is applied as an electron transport layer. Finally, 1nm thick LiF is deposited as an electron injection layer, and then 50nm thick Al is deposited as a cathode to complete the device. In an inert nitrogen atmosphere with less than 1ppm water and oxygen, the device is sealed with a glass cover and a getter. In order to characterize the OLED, electroluminescence (EL) spectra were recorded at various currents and voltages. At 10mA / cm 2 The EL peak maximum value and full width at half maximum (FWHM) were recorded at 10 mA / cm2. In addition, the current-voltage characteristics were measured in combination with the brightness to determine the luminous efficiency and external quantum efficiency (EQE). 2 The driving voltage (voltage) is given at a current density of 50 mA / cm 2 The lifetime of the OLED devices was measured as the brightness decayed to 95% of its initial value at a constant current density of 1.3 Å. The device results are shown in Table 1.

[0978]

[0979]

[0980] Application Example 2

[0981] Example 1 was repeated except that Compound 2 was used in the emitter layer instead of Compound 1. The device results are shown in Table 1.

[0982]

[0983] Comparative Application Example 1

[0984] Example 1 was repeated except that comparative compound 1 was used in the emitter layer instead of compound 1. The device results are shown in Table 1.

[0985]

[0986] Table 1

[0987] Application Examples Emitter EL max, nm <![CDATA[LT95 1) ,%]]> Application Example 1 Compound 1 462 112 Application Example 2 Compound 2 452 104 Comparative Example 1 Comparative Compound 1 462 100

[0988] 1) Using the following formula, relative to the device life of Comparative Example 1, at 50 mA / cm 2 The current density is 50 mA / cm 2 The device life is measured at 95% of the following:

[0989]

[0990] These results demonstrate that the lifetime (LT95) is improved when the compound of the present invention is used as the fluorescent emitting material instead of the comparative compound.

[0991] Application Example 3

[0992] Example 1 was repeated except that compound 4 was used in the emitter layer instead of compound 1. The device results are shown in Table 2.

[0993] Application Example 4

[0994] Example 1 was repeated except that Compound 5 was used in the emitter layer instead of Compound 1. The device results are shown in Table 2.

[0995] Application Example 5

[0996] Example 1 was repeated except that Compound 6 was used in the emitter layer instead of Compound 1. The device results are shown in Table 2.

[0997] Application Example 6

[0998] Example 1 was repeated except that Compound 7 was used in the emitter layer instead of Compound 1. The device results are shown in Table 2.

[0999] Application Example 7

[1000] Example 1 was repeated except that Compound 8 was used in the emitter layer instead of Compound 1. The device results are shown in Table 2.

[1001] Application Example 8

[1002] Example 1 was repeated except that compound 11 was used in the emitter layer instead of compound 1. The device results are shown in Table 2.

[1003] Application Example 9

[1004] Example 1 was repeated except that compound 12 was used in the emitter layer instead of compound 1. The device results are shown in Table 2.

[1005] Application Example 10

[1006] Example 1 was repeated except that compound 13 was used in the emitter layer instead of compound 1. The device results are shown in Table 2.

[1007] Application Example 11

[1008] Example 1 was repeated except that compound 14 was used in the emitter layer instead of compound 1. The device results are shown in Table 2.

[1009] Application Example 12

[1010] Example 1 was repeated except that compound 15 was used in the emitter layer instead of compound 1. The device results are shown in Table 2.

[1011] Application Example 13

[1012] Example 1 was repeated except that compound 16 was used in the emitter layer instead of compound 1. The device results are shown in Table 2.

[1013] Application Example 14

[1014] Example 1 was repeated except that compound 17 was used in the emitter layer instead of compound 1. The device results are shown in Table 2.

[1015] Application Example 15

[1016] Example 1 was repeated except that compound 18 was used in the emitter layer instead of compound 1. The device results are shown in Table 2.

[1017] Application Example 16

[1018] Example 1 was repeated except that compound 19 was used in the emitter layer instead of compound 1. The device results are shown in Table 2.

[1019] Application Example 17

[1020] Example 1 was repeated except that Compound 21 was used in the emitter layer instead of Compound 1. The device results are shown in Table 2.

[1021] Application Example 18

[1022] Example 1 was repeated except that compound 23 was used in the emitter layer instead of compound 1. The device results are shown in Table 2.

[1023] Application Example 19

[1024] Example 1 was repeated except that compound 24 was used in the emitter layer instead of compound 1. The device results are shown in Table 2.

[1025] Application Example 20

[1026] Example 1 was repeated except that compound 25 was used in the emitter layer instead of compound 1. The device results are shown in Table 2.

[1027] Application Example 21

[1028] Example 1 was repeated except that compound 26 was used in the emitter layer instead of compound 1. The device results are shown in Table 2.

[1029] Comparative Application Example 2

[1030] Example 1 was repeated except that comparative compound 2 was used in the emitter layer instead of compound 1. The device results are shown in Table 2.

[1031]

[1032]

[1033]

[1034] Table 2: Results of application examples

[1035]

[1036]

[1037] 2) EQE relative to Comparative Example 2 calculated using the following formula, at 10 mA / cm 2 The EQE of the device measured at a current density of

[1038]

[1039] 3) The device life relative to Comparative Example 2 calculated using the following formula, at 50 mA / cm 2 The current density is 50 mA / cm 2 The device life is measured by 95% of

[1040]

[1041] These results demonstrate that when the compound of the present invention is used instead of Comparative Compound 2 as the fluorescent emitting material, the lifetime and / or efficiency is improved.

Claims

1. Compound represented by formula (I) in R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 20 , R 21 , R 22 , R 23 and R 24 Each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 30 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 30 ring atoms; unsubstituted or substituted aralkyl having 7 to 30 carbon atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted alkyl halide having 1 to 20 carbon atoms; unsubstituted or substituted alkenyl having 2 to 20 carbon atoms; unsubstituted or substituted alkynyl having 2 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; CN; NO2; OR 30 SR 31 ; C(=O)R 32 ;COOR 33 ;SiR 34 R 35 R 36 NR 84 R 85 or halogen; or Two adjacent residues together form an unsubstituted or substituted ring structure, preferably an unsubstituted or substituted alkyl ring; in R 1 , R 2 , R 3 and R 4 At least one, preferably R 2 and R 3 represents at least one of unsubstituted or substituted alkyl having 1 to 20 carbon atoms, or unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms, or two adjacent residues R 1 , R 2 , R 3 and R 4 , preferably R 2 and R 3 together form an unsubstituted or substituted alkyl ring; R 5 , R 6 , R 7 and R 8 At least one, preferably R 6 and R 7 represents at least one of unsubstituted or substituted alkyl having 1 to 20 carbon atoms, or unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms, or two adjacent residues R 5 , R 6 , R 7 and R 8 , preferably R 6 and R 7 together form an unsubstituted or substituted alkyl ring; and R 21 , R 22 and R 23 At least one representative group HAr; Y represents a group HAr or R Y ,in R Y represents hydrogen; unsubstituted or substituted aryl having 6 to 30 ring carbon atoms; unsubstituted or substituted N-heteroaryl having 5 to 30 ring atoms; unsubstituted or substituted aralkyl having 7 to 30 carbon atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted alkyl halide having 1 to 20 carbon atoms; unsubstituted or substituted alkenyl having 2 to 20 carbon atoms; unsubstituted or substituted alkynyl having 2 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; CN; NO2; OR 30 SR 31 ; C(=O)R 32 ;COOR 33 ;SiR 34 R 35 R 36 NR 84 R 85 or halogen; or R Y Forming an unsubstituted or substituted ring with the adjacent residue at L; and HAr represents a group of formula (II) in R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 Each independently represents hydrogen; unsubstituted or substituted aryl having 6 to 30 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 30 ring atoms; unsubstituted or substituted aralkyl having 7 to 30 carbon atoms; unsubstituted or substituted alkyl having 1 to 20 carbon atoms; unsubstituted or substituted alkyl halide having 1 to 20 carbon atoms; unsubstituted or substituted alkenyl having 2 to 20 carbon atoms; unsubstituted or substituted alkynyl having 2 to 20 carbon atoms; unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms; CN; NO2; OR 30 SR 31 ; C(=O)R 32 ;COOR 33 ;SiR 34 R 35 R 36 NR 84 R 85 or halogen; or Two adjacent residues together form an unsubstituted or substituted ring structure; R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 and R 19 One is the bonding site; X is O, S or CR 25 R 26 ; L represents an unsubstituted or substituted divalent aryl group having 6 to 30 ring carbon atoms; an unsubstituted or substituted divalent heteroaryl group having 5 to 30 ring atoms; an unsubstituted or substituted divalent alkyl group having 1 to 20 carbon atoms; or an unsubstituted or substituted divalent cycloalkyl group having 3 to 20 ring carbon atoms; R 30 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 each independently represents an unsubstituted or substituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 30 ring atoms; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms; R 25 , R 26 each independently represents an unsubstituted or substituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 30 ring atoms; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms; or R 25 and R 26 together to form an unsubstituted or substituted ring structure; R 84 and R 85 each independently represents an unsubstituted or substituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 30 ring atoms; an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms; or together to form an unsubstituted or substituted ring structure; n represents 0, 1, 2 or 3; preferably 0, 1 or 2; more preferably 0 or 1.

2. The compound according to claim 1, wherein R 2 and R 3 At least one of represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms, or R 2 and R 3 Together they form an unsubstituted or substituted ring structure, preferably an unsubstituted or substituted alkyl ring.

3. The compound according to claim 1 or 2, wherein R 6 and R 7 At least one of represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms, or R 6 and R 7 Together they form an unsubstituted or substituted ring structure, preferably an unsubstituted or substituted alkyl ring.

4. The compound according to any one of claims 1 to 3, wherein R 9 , R 10 and R 11 At least one, preferably R 10 represents hydrogen, unsubstituted or substituted alkyl having 1 to 20 carbon atoms, or unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted or substituted aryl having 6 to 30 ring carbon atoms; unsubstituted or substituted heteroaryl having 5 to 30 ring atoms; NR 84 R 85 ,or R 9 and R 10 , and / or R 10 and R 11 Together they form an unsubstituted or substituted ring structure, preferably an unsubstituted or substituted alkyl ring.

5. The compound according to any one of claims 1 to 4, wherein R 22 is HAr, or R 21 It's HAr.

6. The compound according to any one of claims 1 to 5, wherein n is 0 or 1.

7. The compound according to any one of claims 1 to 6, wherein the compound is represented by one of the following formulae 8. The compound according to any one of claims 1 to 7, wherein R 1 , R 4 , R 5 , R 8 , R 9 , R 11 , R 20 and R 24 is hydrogen; or R 1 , R 4 , R 5 , R 8 , R 9 and R 11 is hydrogen, and R 20 and R 24 Each independently represents hydrogen or an aryl group having 6 to 30 ring carbon atoms.

9. The compound according to any one of claims 1 to 8, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 11 Does not represent amino NR 84 R 85 .

10. The compound according to any one of claims 1 to 9, wherein the compound is represented by one of the following formulae in R 1 , R 4 , R 5 , R 8 , R 9 , R 11 , R 20 and R 24 is hydrogen; or R 1 , R 4 , R 5 , R 8 , R 9 and R 11 is hydrogen, and R 20 and R 24 each independently represents hydrogen or an aryl group having 6 to 30 ring carbon atoms; R 2 and R 3 At least one of the residues R represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms, and the remaining residues R 2 or R 3 is hydrogen; or R 2 and R 3 together form an unsubstituted or substituted alkyl ring; R 6 and R 7 At least one of the residues R represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms, and the remaining residues R 6 or R 7 is hydrogen; or R 6 and R 7 together form an unsubstituted or substituted alkyl ring; R 10 represents hydrogen, unsubstituted or substituted alkyl having 1 to 20 carbon atoms, unsubstituted or substituted cycloalkyl having 3 to 20 ring carbon atoms or NR 84 R 85 ; or an aryl group having 6 to 30 ring carbon atoms; R Y represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, or an unsubstituted or substituted cycloalkyl group having 3 to 20 ring carbon atoms, or R Y Together with the adjacent residue at L, it forms an unsubstituted or substituted alkyl ring; or R Y represents hydrogen or an aryl group having 6 to 30 ring carbon atoms; R 84 and R 85 Each independently represents an unsubstituted or substituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted or substituted heteroaryl group having 5 to 30 ring atoms; L represents unsubstituted or substituted phenylene; and n is 0 or 1.

11. A material, preferably an emitter material, for an organic electroluminescent device, comprising at least one compound according to any one of claims 1 to 10.

12. An organic electroluminescent device comprising at least one compound according to any one of claims 1 to 10.

13. The organic electroluminescent device according to claim 12, comprising a cathode, an anode and one or more organic thin film layers including an emission layer arranged between the cathode and the anode, wherein at least one layer of the organic thin film layers comprises at least one compound according to any one of claims 1 to 10.

14. The organic electroluminescent device according to claim 13, wherein the light emitting layer comprises at least one compound according to any one of claims 1 to 10. 15 . The organic electroluminescent device according to claim 14 , wherein the light emitting layer comprises at least one host and at least one dopant, wherein the dopant comprises at least one compound according to any one of claims 1 to 10 . 16 . The organic electroluminescent device according to claim 15 , wherein the host comprises at least one substituted or unsubstituted fused aromatic hydrocarbon compound and / or at least one substituted or unsubstituted anthracene compound.

17. The organic electroluminescent device according to claim 16, wherein the anthracene compound is represented by the following formula (10): in Two or more adjacent R 101 To R 110 One or more pairs of may form a substituted or unsubstituted, saturated or unsaturated ring; R does not form a substituted or unsubstituted, saturated or unsaturated ring 101 To R 110 independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 50 carbon atoms, a substituted or unsubstituted alkylene group including 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group including 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group including 7 to 50 carbon atoms, -Si(R 121 )(R 122 )(R 123 ), -C(=O)R 124 、-COOR 125 、-N(R 126 )(R 127 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or a group represented by the following formula (31); R 121 To R 127 are independently a hydrogen atom, a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; when R 121 To R 127 When multiple R 121 To R 127 Each can be the same or different; Provided that there is no R forming a substituted or unsubstituted, saturated or unsaturated ring 101 To R 110 At least one of the groups is a group represented by the following formula (31). If there are two or more groups represented by the formula (31), these groups may be the same or different; -L 101 -On 101 (31) In formula (31), L 101 is a single bond, a substituted or unsubstituted arylene group containing 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group containing 5 to 30 ring atoms; Ar 101 is a substituted or unsubstituted aryl group comprising 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group comprising 5 to 50 ring atoms.

18. An electronic device comprising the organic electroluminescent device according to any one of claims 12 to 17.

19. A light emitting layer comprising at least one host and at least one dopant, wherein the dopant comprises at least one compound according to any one of claims 1 to 10.

20. Use of a compound of formula (I) according to any one of claims 1 to 10 in an organic electroluminescent device.

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