TW201204728A - Condensed-cyclic compound and organic light-emitting device including the same - Google Patents

Abstract

A condensed-cyclic compound and an OLED including the same, the condensed-cyclic compound represented by Formula 1 below.

Description

201204728 VI. Description of the Invention: [Technical Field of the Invention] [0001] Embodiments of the present invention relate to an organic light-emitting device for condensing a cyclic condensed cyclic compound. And I3 the text _2] organic light-emitting devices (OLEDs), which are self-luminous cracking, 1, for example: wide viewing angle, superior pair, lower advantage contrast, fast response, high meaning [0003]

Degree, superior drive voltage characteristics and multi-color images. 4 A representative organic light-emitting device may have an upper structure, such as: a substrate and sequentially stacked on the substrate, J-etching, lightning, and π fine transport layer (HTL), Emissive layer (10)), electron transport layer (ETL) and cathode. In this regard, the hole transport layer and the emissive layer may be organic thin films formed of organic compounds. The operation principle of the organic light-emitting device having the above structure is as follows. a --voltage is applied between the anode and the cathode, the hole injected from the anode is moved to the emissive layer via the hole transport layer, and the electrons injected from the cathode are moved to the emissive layer via the electron transport layer and the hole These electrons are recombined at the emissive layer to generate excitons. When the excitons drop from the excited state to the ground state, light is emitted. SUMMARY OF THE INVENTION An embodiment of the invention is characterized by providing a condensed cyclic compound and an organic light-emitting device comprising the condensed cyclic compound. The above-mentioned and other features and advantages of the following formula 1 [0007] are achieved by providing a condensed cyclic compound represented by the following formula: 州妙切4一0 100111378 Form No. A0101 Page 3 of 88 201204728

Wherein, in Formula 1: The A ring system is represented by the following Formula 2 or Formula 3:

R 11 R 12 R#R12 is a hydrogen atom, a heavy hydrogen atom (gas), a sulfhydryl group of a sulfhydryl group, a substituted or unsubstituted alkyl group. a c2-c3G dilute group, a di- or di-substituted C2-C3G block group, a substituted or unsubstituted c-c alkoxy group, and a -(Ar) _ 1 30 1 a A II The first substituent represented by _ Nf-(Ar2)b-Ar]2Jf.(A } _ 3 c ΛΓ] 3_Ι represents the second substituent 100111378 Form No. AOJOl 1003273214-0 201204728 or one by a third substituent represented by -(Αι·4)(1-Ν[-(Αγ5)γΑΓι5][_(Αγ6)厂ΑΓι6], at least one of \ to 1?12 is a third substituent; From the substituents to the third substituents, the human to the human are each a substituted or unsubstituted aikylene gr〇up, a substituted or unsubstituted (: 2-(:3) () an akenenyiene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted cc heteroaryl group 3 3 0 (heteroarylene group);

100111378 A from the first substituent to the third substituent. 】, Αι·ι2, Ar^, Αι_ and Ari6 are each a hydrogen atom, a heavy hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted c « 1 30 condition base, once a substituted or unsubstituted CrC3G alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted C5_C3 fluorenyl group or a "di- or unsubstituted" C3-C3()heteroaryl; a 'b, c, e, and f are each an integer from 〇 to 1〇; d is an integer from 0 to 10; and 'ι's 'V, group at first The groups of the substituent _(ΑγΛ士" are identical or different from each other; the Ar·, "b" group is the same or different from each other in the -(Arp^Ar2) group of the second substituent; 3 ^ In the second substituent, the members of the group 13 are identical or different from each other; the group of Ar^ "e" in the base of the third substituent is the same or different from each other, · A# "f The group is identical or different from each other in the -(Αι·6)γΑι·16 group of the third substituent.

Ar# Ar6 may each be a substituted or unsubstituted c"c aryl or a substituted or unsubstituted W heteroaryl. 14 square form number A0101 page 5 / 88 pages 1003273214-0 201204728 [0008] 100111378

Ari to Ar6 may each be a stupid base, a Ci_CH alkyl phenyl group, a bis(CrCio alkyl) group, a (C6-Cu aryl) phenyl group, a one (%. 14 basis) Stretching phenyl, carbazoly 1 ene group, one (: plant (: 1 () alkyl extended carbazolyl, monoalkyl) carbazolyl, a crcH aryl carbazole, one Bis(c6-c14 aryl) stretching leaves 'fluorenylene group, fluorenylene group, one (^-(^1(} alkyl-alkyl group, one-two (C-C alkyl)), one , aryl 1 1 υ 6 14 ) anthracene, a di-(c6-cl4 aryl) fluorenyl group, a naphthylene group, a -(:1{)alkyl-naphthyl group, one or two ( Ci-C1 nonylalkyl) anthranyl, mono(C6-Ch aryl) anthranyl, one (C6_C14^•))naphthyl, an anthranylene group, one (^-(:1) Alkylalkylene, a bis(crc1 alkyl)alkyl group, a (C6_C14 aryl) thiol group, a bis(C6_C14 aryl) thiol group, a pyridinylene group, a (: "(: alkyl-pyridyl, mono-dialkyl)-pyridyl, one (c6-c14 aryl) Pyridyl group 'a*-(Cg-Cid square basis) is more than 唆 base, ~~ quinol inylene group, one (: "(:"alkyl quinolinyl, one or two ( C^-Cw alkyl) quinolinyl, one (c6-ci4 aryl) quinolinyl, one (two (C6~*C14 aryl)), a phenyl group, and a benzoimidazolylene group ), one (^-(: 丨. alkyl-benzimidazolyl, mono-dialkyl)-benzimidazolyl, one ((:6-(:14 aryl)) and tastes olfactory, one-one (Cg-Ci4 square base) benzoin 11 base, a stretch imidazopyrimidiny lene group >

Ci-C1Q alkyl extended imidazolium pyridyl, one (two: (1) alkyl) imidazolidine, one (c6-cl4 aryl) imidazolidine, one (two (c6-cl4 aryl)) Stretching taste ° sitting π than bite base, a stretched rice β sitting 0S bite base form number Α 0101 Page 6 / a total of 88 pages 1003273214-0 201204728 (imidazopyrimidinylene group), one (^-c burnt imidazolidine, one or two (crciG Alkyl) an imidazolyl pyridyl group, a (CrCi4 aryl) an imidazolidinyl group or a bis(CrCi4 aryl) an imidazolidinyl group. [A] Aril 'Ar! 2, Ari3, Αι·ΐ5, and Ari6 can be individually Is a hydrogen atom, a monohydric hydrogen atom, a halogen atom, a monohydroxy group, a monocyano group, a substituted or unsubstituted (: (1) alkyl group, a substituted or unsubstituted c-C10 alkenyl group a substituted or unsubstituted c2_CiQ alkynyl'-substituted or unsubstituted C1_C1Q alkoxy group, a substituted or unsubstituted C-C14 aryl group or a substituted or unsubstituted (:c heteroaryl group) 〇14 _] Aru, Ar12, Ari3, Arl5 and Ar16 can each be a hydrogen atom, a heavy IL atom, a halogen atom, , monocyano 'monomethyl, monoethyl, monopropyl, monobutyl, monodecyl, monovinyl, monopropenyl, monobutenyl, -pentenyl, monoethylidene, monomethyl Oxyl, monoethoxy, monopropoxy, monobutoxy, monopentyloxy, monophenyl, mono-Ci-C1-decylphenyl, di-(CrCi〇alkyl)phenyl, one ( C^Ch aryl) stupid, one (C6_C14 aryl) phenyl 'carbazolyl group, one 〇 factory (: 1 () alkyl oxazolyl 'two (Cl_Cio alkyl) 咔Azolyl, a C6-C" arylcarbazolyl, a bis(C6-Cl4 aryl)carbazolyl group, a fluorenyl ruthenium group, a c"c1() fluorenyl group, One or two (crc1 fluorenyl) fluorenyl, one (c6_ci4 aryl) group, one (C6_C14 aryl) group, naphthyl group, one C]-C1 () alkylnaphthyl group, one Bis(c)-(alkyl)naphthyl, mono(C6-C14 aryl)naphthyl, mono-(C6-Cu aryl)naphthyl, anthryl group, a Ci_Ci decylalkyl group, one Two (Ci_Ci〇100111378 Form No. A0101 Page 7 / Total 88 Page 1003273214-0 201204728 Alkenyl) a (c6-cl4 aryl) fluorenyl group, a bis(C6-C14 aryl) fluorenyl group, a pyridinyl group, a pyridyl group, a monoalkylpyridyl group, a dialkyl)pyridyl group , a (Cc-Ci4 aryl) ° bite base, one or two (Cc-C1/t aryl) ° bite base, a quinolinyl group, a (^-(^ burnt quinolinyl, Mono-αΓ(:1()alkyl)quinolinyl, mono(c6-cl4 aryl)quinolinyl, mono-(Cc-C1y1 aryl)quinolinyl, monobenzimidazolyl D 14 (benzoimidazolyl group ), one (: 丨-C1 () alkyl benzimidazolyl, one (two 〖c1 () alkyl) benzimidazolyl, one (c6-c14 aryl) benzimidin, one two (C6_Ci4 aryl) stupid and savoury "sit on the base, just swear!" than the imidazopyridinyl group, one (^-(: 丨. Alkyl imidazolidinyl, mono-ααΓ(:1()alkyl)imidazolidinyl'-(CrCi4 aryl) imi. Sit 0 than the bite base, one (C δ - C1 4 ^ • base). It is more than a bite base, an imidazopyrimidinyl group, a (^-C^ burnt base, a pyrimidine group, a two (Ci_Ci) group, an imidazolyl group, a ((^-(:丨) Aryl) imipenem or a bis (c6_c14 aryl) meth.

Any one of 4A to 4G indicates: , Ar" 'Ar1t; and Ar 16 can each be independently of the following formula

Form 4G Form No. A0101 Page 8/88 Page 100111378 1003273214-0 201204728 '2] and wherein Z, Z'z and 7仫々 of the formulas 4A to 4G, the technique 1 2 and the Z12 are each a gas atom , a heavy hydrogen atom, a C _c pa, r ο 1 Ll 〇 pit base, a C!-, alkoxy or —crCM aryl, P and q are each an integer of 1 to 8, and The bonding position of Ari, Ar2, Ar3, Ar5 or Ar. [0013] Ar

Any one of Ari2' Aris 5A to 5E is represented by:

Ari5 and Arle are each by the following formula

_5匸

Equation 5A

And wherein, in the formulae 5A to 5E, * is - and Aq, Ar2, A, or Ar. The bonding position. a[0014] a, b, c, e, and f are each independently 〇, i, 2, or 3, and 2, or [0015] a second substituent and a third substituent -N[-(Ar5)e -Ar15][~(Ar6)f-Ari6] can each be represented by any one of the following formulas 6A to 6K: 100111378 Form No. A0101 Page 9 / Total 88 Page 1003273214-0 201204728

And wherein, in the formulas & A to 6Κ, 2丨 to 24 and Zu to ZH each are independently a hydrogen atom, a heavy hydrogen atom, a Ci-ci () alkyl group, a Ci-Cw alkoxy group or a C6 -C14 aryl, p, q, r and s are each an integer of one, and * is a bonding position with Ar4 or a ring atom of a backbone of formula 1. [0016] 100111378 \ to ^ 12 may each be the one atom, one heavy hydrogen atom, one halogen atom, one hydroxyl group, one cyano group, the first substituent, the second substituent or the third substituent; "a "In the first substituent is 〇; "b" and "c" in the second substituent are each 0 or 1; d in the third substituent is 1 or 2, and "e" and "f" The disubstituted groups are each independently 0 or 1; the Δ1*2 to 41'6 in the order of the first substituent to the third substituent are each a substituted or unsubstituted C5-Ci4 aryl group or Is a substituted or unsubstituted cc heterosexual 3 14

And AA 11 1 ί· , Ari 3 , Ar 15 and Ar 16 among the first substituent to the third substituent are each a hydrogen atom, a mono hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted Ci-Cio alkyl group, a substituted or unsubstituted C2-ClQ alkenyl group, a substituted or unsubstituted c2-ciq alkynyl group, a substituted or unsubstituted Ci_Ci decyloxy group A substituted or unsubstituted C5-C aryl group or Form No. A0101 Page 10 of 88 5 14 ι〇〇3273214-0 201204728 A substituted or unsubstituted aryl group. 〇14 t0017] Ri to Ri2 may each independently be a hydrogen atom, a monohydric hydrogen atom, a halogen atom, a monohydroxyl-cyano group, a first substituent, a second substituent or a third substituent; "a" The first substituent is 〇; "b" and "c" in the second substituent are each 0 or 1; d in the third substituent is 丨 or 2, and "e" and "f" in the third substitution Each of the base systems is 〇 or 1; the Αι~2 to Ar6 series among the first substituent to the third substituent are each a phenyl group, a (^-(^ 〇 基 phenyl), a bis ( CrCi 〇 alkyl) phenyl, mono(C6-Cu aryl) phenyl-(C6_C14^•) phenyl, a stimulating thiol, a Ci_Ci 〇 伸 base, one by one (Cl- CiQ is based on a sulfhydryl group, a (^-C aryl carbazolyl group, a bis(C6-CI4 aryl) carbazole group, a thiol group, a Ci_C10 yard base, a bis (^) -C1() 炫基)Extended base, one (C6_C14 aryl) extended base, one (two (C6-CH aryl)) thiol, one extended naphthyl, one (: factory (: 1 () alkyl Base, one two (C plant C1Q alkyl) stretching naphthyl, one (CrCi4萘Naphthyl '-di(C6-C14 aryl)-naphthyl, a fluorenyl group, a monoalkyl fluorenyl group, a bis((^-'0 alkyl) fluorenyl group, a (C6_C14 aryl group) a fluorenyl group, a bis(C6-C14 aryl) thiol group, a pyridine group, a monoalkylpyridyl group, a bis(Ci_Ci() alkyl) pyridine group, a (C6-C14 aryl group) Pyridyl, mono-(C6_Ci4 aryl) extension ratio bite group, hexakila group, thiophene quinolyl group, 1-2 (C^-Cb alkyl group) quinolinyl group, one (C6-Cl4 aryl group) a quinolinol group, a bis(C6-C14 aryl) quinolinol group, a benzzimidazolyl group, a C1_C1G alkyl group, a strepinium imidazolyl group, a bis(Ci_C1G alkyl group), a streptozolyl group, and an imidazole group. C6-C14 aryl) is stupid and imidazolyl, one or two (Cg_Cl4 aryl) is stupid and smells olfactory, a taste is more than a bite base, a 100111378 Form No. 1010101 No. 11 1/ Total 88 pages 1003273214-0 201204728 a 10 alkyl extended imidazolium pyridyl group, a di(CrCiQ alkyl) imidazolidine pyridyl group, a (crcM aryl) imidazolidine pyridyl group, a bis(\_Ci4 aryl group) extensible salivary group, a stretching (four) base group, -c1-ci(^基伸咪, pyridine, one or two (CrCi 〇 alkyl) imidazolyl pyridyl, one (C6-C14 aryl) stretching rice sitting bite base or - two (Ά 4 aryl) stretching taste mouth bite base;

Among the one substituent to the third substituent, A Ar , Ar , A 1 1 12 13 ΛΓ 15 and Aru are each independently a hydrogen atom, a heavy hydrogen atom, a dentate atom, a hydroxyl group, a cyano group, and a Methyl, -ethyl, monopropyl-butyl, monopentyl, monovinyl, monopropenyl, monobutenyl, monopentenyl, -ethyl, methoxy, monoethoxy '-propoxy, monobutoxy, -pentyloxy, -phenyl, alkylphenyl, mono-(Ci_C1()alkyl)phenyl, -(C6-CHaryl)phenyl, -di Aryl) phenyl, ... carbyl, -crCi oxime, succinyl, bis (c "4 c1 fluorenyl" oxime, a c6-ci4 aryl sulphate, one or two (c6_c^ ^ base) carbazolyl, a fluorenyl group, a C plant Cl 〇 alkyl group, a bis (Cl-Ci 〇 alkyl) group, a (C6-C14 aryl) fluorenyl group, a two (cc fang a b14 group, a naphthyl group, a C1-C1G alkylnaphthyl group, a bis ((: (1) alkyl) naphthyl group, a (C6_CI4 aryl) naphthyl group, a bis (C6) -C14 aryl)naphthyl, anthracenyl, one (: factory (: 1 〇 蒽 base, one two (c plant L Hyun) sulfhydryl, one (C6- C14 aryl) fluorenyl, bis(Crci4 aryl) fluorenyl, ... specific crosslink, a Ci_C1Q base, bite base, one or two (C plant C1G 垸 base bite base, one (CrCi4 aryl) pyridine , bis(CrCl4 aryl)pyridinyl, monoquinolyl, monoalkylquinolinyl, mono-(C1-CB alkyl)quinolinyl, mono(C6-C14 aryl)quinolinyl, one or two ( C6-C14 aryl)quinolinyl, monobenzimidazolyl, a C1_C1Q alkyl benzoimidazolyl, a bis((: 丨-(:1{) alkyl) benzimidazolyl, a (c6-cl4) Aryl) stupid imidazolyl, one or two 100111378 Form No. A0101 Page 12 / 88 pages 1003273214-0 201204728 Factory C aryl) benzo 17 m saliva, one taste ° σ than the base, a C_C yard 6 14 110 米 吼 吼 吼 〜 一 一 一 一 一 一 一 一 一 一 一 〜 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 Rice. Sitting on the σ 唉 base, one taste 6 14 ° sitting mouth deciduous base, a burning base taste ° sitting mouth bite base, one or two base) taste. Sitting on the base, one (cc aryl) taste spit bite base Or one or two 6 14 (C-Cl4 aryl) taste. Sit down the base. Ό [0018] Ο by Formula 1 The condensed cyclic compound represented by any one of the following formulas 2a to 2d of those represented by: c r2

Equation 2d

Wherein, in the formula 2a to the formula 2d, 1^ to 1?12 each is a hydrogen atom, a monohydrogen atom, a halogen atom, a mono-, a cyano group, a substituted or unsubstituted C^-C^ Alkyl, monosubstituted or unsubstituted C2-C3() 100111378 Form No. A0101 Page 13 of 88 1003273214-0 201204728 Dilute, substituted or unsubstituted (tetra) alkynyl, substituted or unsubstituted a substituted crc3#oxy group, a first substituent, a second substituent or a second substituent; wherein the first to the third substituents to the red 6 series are each a single or unsubstituted c] _C3 〇 烧, a substituted or unsubstituted W group, a substituted or unsubstituted C5^3G extended aryl ' _ substituted or unsubstituted aryl extended substituent to The A, .11 12 Λ1ΐ3 15 and Arl6 systems in the disubstituted group are each independently a hydrogen atom, a monohydric hydrogen atom, a halogen atom, a thiol group, a cyano group, a substituted or unsubstituted group.

CrC3(), substituted or unsubstituted alkenyl, substituted or unsubstituted c2-c3() silk, once substituted or unsubstituted

Cl alkoxy, a substituted or unsubstituted C5_CM aryl or a substituted or unsubstituted CrC3 doped aryl; a, b, Γ, (8) are each independently 0 to 1G-integer; (d) _ An integer; and the "a" group of red 1 is the same or different from each other in the - substituent group; the "b" group of As in the second substituent - (a,) The groups in the plant group are the same or different from each other; the groups of the group are in the same or different from each other in the _ (Ar3)c-Aru group of the second substituent; the "e, group is in the third substitution The _(Αγ5)ΓΑγ15 groups in the group are the same or different from each other; the f-Ar16 groups are in each other

The "f" group of Ar6 is the same or different in _(Ar)6 of the third substituent. [0019]

Ar4 may comprise a phenyl group, a monoalkyl group, a bis(C^Cio alkyl) phenyl group, a (c6-ci4 aryl) phenyl group, a bis (crcH aryl) phenyl group, a stretch Benzazolyl, a Ci_Ci 〇 alkyl carbazolyl, a bis (crc1 () alkyl) oxazolyl, a C6_C" aryl extension 100111378 Form No. A0101 Page 14 of 88 1003273214-0 201204728 Azolyl , a bis(c6-c14 aryl) carbazolyl group, a stretching group, a _q-Cio alkyl group, a bis(c^Ch alkyl) group, and a (C6-Ci4 aryl group) Sulfhydryl, bis(C&-C14 aryl) anthracene, an extended naphthyl group, a crclG alkylnaphthyl group, a di(crc1()alkyl)naphthyl group, a (c6-c14 aryl) group Naphthyl, bis(c6-ci4 aryl)naphthyl, an extended fluorenyl group, a Crcl0 alkyl hydrazino group, a bis(crcl()alkyl) thiol group, a (c6-cl4_ group) hydrazine And at least one of a bis(c6-ci4 aryl) thiol group; and d can be 1, 2 or 3. [0020] The second substituent and the -N[-(Ar5)e-Ar15][-(Ar6)f-Aru] of the third substituent are each represented by any one of the following formulas 6A to 6K; :

And in the formulas 6A to 6K, is it verbose? 4 and Zu to Zu are each a hydrogen atom, a heavy hydrogen atom, a (: (1) pyrolyzed, a Ci-ci {) alkoxy group or a C6_C14 aryl 'P' q, Γ and Each of the S series is an integer of 1 to 8, and * is a bonding position with a ring atom of Ar4 or a backbone of the formula 1. [0021] The condensed cyclic compound represented by Formula 1 may be represented by the following formula: Any 100111378 of 3a to 3e Form No. A0101 Page 15 / Total 88 Page 1003273214-0 201204728 One of the:

Wherein, in the formulae 3a to 3e, each of the formulae is a hydrogen atom, a heavy hydrogen atom, a halogen atom, a monohydroxy group, a cyano group, a substituted or unsubstituted (^-(:3) () an alkyl group, a substituted or unsubstituted c2-c3() alkenyl group, a substituted or unsubstituted c2-c3() alkynyl group, a substituted or unsubstituted (^-(:3()) An alkoxy group, a first substituent, a second substituent or a third substituent; each of the first substituent to the third substituent is independently substituted or unsubstituted (^-(:3() An alkyl group, a substituted or unsubstituted C2-C3()alkylene group, a substituted or unsubstituted C5-C3() extended aryl group or a substituted or unsubstituted C3-C3 (J) Heteroaryl; Ar,, Ar1(), Ar, Ar, and Ar are each a single hydrogen atom 11 IL 1 ο 1 b 1 ο , a heavy hydrogen atom, a halogen atom, a thiol group, a cyano group, Substituted or unsubstituted 乂% alkyl, substituted or unsubstituted c2-cQn alkenyl, substituted or unsubstituted c9-cqn alkynyl, once substituted

〇U /- o U 100111378 Form No. A0101 Page 16 of 88 1003273214-0 201204728 Or unsubstituted W-based, substituted or unsubstituted C _ C30 aryl or - substituted or not Substituted wheteroaryl; a, "C, (8) are each independently G to 10-integer; <1 is 0 to U) - integer: Ar!"a, group in the -substituent The groups of (AVa' are identical or different from each other; the "b" groups of Ar2 are identical or different from each other in the -(Ar)_Ar12 group of the second substituent; A, „c" In the second di-diyl-(ArPc-Ar!3 group, the same or different from each other; the group of a, in the group of the third substituent is the same or not the same as the same; [0022] the same; The "f" group is the same or different from each other in the _(Α,)" of the third substituent.

Q VIII]: 4 may comprise a phenylene group, a monoalkyl group, a bis(h-ClO alkyl) phenyl group, a (C^C14 aryl) phenyl group, a bis (crci4 aryl) group. Stupid, carbazolyl, monoalkyl carbazolyl, bis(CrClQ alkyl) carbazolyl, one (: 6-(:14 aryl carbazolyl, one bis (C6_C14 aryl)) An azole group, a berry group, a C^Cio alkyl group, a di(Ci_Ci 〇 alkyl) group, a (Ce-Ci4 aryl) group, a two (crCH aryl) group — —Naphthyl, a C 1 —C 1 G alkylnaphthyl group, a bis(CrC1Q alkyl) —naphthyl group, a (C 6 —C 14 aryl) —naphthyl group, a bis(C 6 —Cu aryl) —naphthyl group, , at least one of a C1_C10 stilbene thiol group, a bis(C^-Cio alkyl group) stretching group, a (c6-c14 aryl) stretching group, and a bis(c6-ci4 aryl) stretching group And d is 1, 2 or 3. [0023] The second substituent and the third substituent -N[-(Ar5)e-Ari5][_(Ar6)f-Ari6] may each be independently represented by the following formula: Any of the 6A to 6K's one representation: 100111378 Form No. A0101 Page 17 / Total 88 Page 1003273214-0 201204 728

And in the formulae 6A to 6K, /, to B and verbose to /, each is a single hydrogen atom, a heavy hydrogen atom, a C1 - c ^ alkyl group, a ci - C j ^ alkoxy group or - Ce-C1i (aryl, p, q, r, and s are each an integer from 1 to 8, and * is a bond 4 position with a ring atom of Al or a backbone of formula 1. [0024] At least one of the above and other features and advantages may also provide a first layer including a first electrode, a second electrode relative to the first electrode, and a first electrode and a second electrode (including [0025] The first layer may include a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and an electron injection layer. At least one of the organic light-emitting devices may further include: a hole injection layer, a hole transport layer, an emission layer, a hole blocking layer, an electron transport layer, and an electron injection layer. One of them is between the first electrode and the second electrode. [Embodiment] [0027] Korean Patent Application No. 1 0-201 0-0029992, in April 2010, 100111378 Form No. A0101 Page 18 of 88 1003273214-0 201204728 1曰Application from Korea Intellectual Property Office, and titled Condensed Cyclic Compound And the entire contents of the organic light-emitting device including the condensed cyclic compound, please refer to the following for a full reference. [0028] Hereinafter, the exemplary embodiment and the accompanying drawings will be more completely described, but The "not smothered" form is "implemented" and should not be construed as being limited to the embodiments described below. The embodiments are provided to remove the invention and to fully disclose the present invention. The scope of the invention is fully conveyed to those skilled in the art. [0029] In the drawings, the size and regions of the layers may be exaggerated for clarity. When a layer or element can be described as being on another layer or substrate, " can be interpreted as being directly on other layers or on a substrate, or can be represented as an intermediate layer. Further, when one layer is described as being in another layer, below, it can be interpreted as being directly on the layer. Below and can be expressed In the case of one or more intermediate layers, in addition, when a layer is expressed as a two-layer "between", it can be interpreted as a single layer between two layers, or can be represented as one or more intermediate layers. [0030] According to an embodiment, a condensed cyclic compound is represented by the following formula 1.

In Formula 1, one ring system is represented by the following Formula 2 or Formula 3: 100111378 Form No. A0101 Page 19 of 88 1003273214-0 201204728

Ο

[0032] In Formula 1, C1 is the same as \ in Formula 2 and q in Formula 3. Further, in the formula 1, it is the same as C2 in the formula 2 and C2 in the formula 3. In the formulas 2 and 3, ΉΙ2 may be each independently, for example: a hydrogen atom, a hydrogen atom, a radical, an aryl group, a substituted or untwisted \, silk, - substituted or not Substituted, substituted or unsubstituted %, block group once substituted, alkoxy, - by - (AriV, represented by the first b (Ar2VA,] [' (w13] a substituent and/or a second substituent represented by '(AVdKAVe-'5][-(AVf_Ari6), which is at least _(^) from % to 1?12"

Nf (Ar5)e-ArJ5]f-(Ar6) Plant Ary, ie, Third Substituent 100111378 Form No. AOiOi Page 20 of 88 Page 323273214-0 201204728 [0033] First Substituent to Third Substituent A 'C. _C30 alkylene gr*Qup, a substituted or unsubstituted alkenylene group, once substituted or unsubstituted Substituted W-aryl ((4) group coffee group) and/or substituted or unsubstituted % 杂 heteroarylene group. For example, '^丨 to 釺6 can be each independently-substituted or unsubstituted W-aryl and/or disubstituted or unsubstituted aryl, but not limited to i when implemented Ο [0034] Αι:2 to Ar& can each be a substituted or unsubstituted 〇_c stretching t 5 14 τ ^ group. For example, among the first substituent to the third substituent, each of the groups may be a substituted or unsubstituted extended, unsubstituted or unsubstituted cyclodene. Pentalenylene gr〇up, substituted or unsubstituted indenylene gr〇up, ❹ substituted or unsubstituted anthranyl group, substituted or unsubstituted azulenylene group a substituted or unsubstituted heptalenylene group, a substituted or unsubstituted, indacenylene gr〇up, a substituted or unsubstituted stretched ethylene An acenaphthylene group, a substituted or unsubstituted extended group, a substituted or unsubstituted phenalenylene group, a substituted or unsubstituted phenanthrenylene group, once substituted Or unsubstituted thiol, substituted or unsubstituted fluoranthenylene group, substituted or unsubstituted terphenylenylene group, 100111 378 Form No. A0101 Page 21 of 88 1003273214-0 201204728 A substituted or unsubstituted pyronyleny lene grc up), a substituted or unsubstituted chrysenylene group, once substituted or Unsubstituted naphthacenylene group, substituted or unsubstituted picenylene group, substituted or unsubstituted perylenylene group, substituted or unsubstituted a pentaphenylene group, a substituted or unsubstituted hexacenylene group, a substituted or unsubstituted pyrrolylene group, a substituted or unsubstituted stretch Pyrazyl 1ylene group, substituted or unsubstituted imidazoly lene group, substituted or unsubstituted imidazolinylene group, substituted or unsubstituted伸咪0 sits°Imidazopyridinylene group, once substituted or unsubstituted, imidazopyrimidinylene group, once substituted or Substituted stretch. Pyridyl group, substituted or unsubstituted pyrazinylene group, substituted or unsubstituted stretched bite group, substituted or unsubstituted indolylene group, - Substituted or unsubstituted thiol group, substituted or unsubstituted quinolinylene group, substituted or unsubstituted phthalazinylene group, substituted or unsubstituted Indo 1 izi ny 1 ene group, a substituted or unsubstituted naphthyridinylene group, a substituted or unsubstituted oxazoline group, once substituted or Unsubstituted Ding Xinlinji 100111378 Form No. A0101 Page 22 of 88 1003273214-0 201204728

(cinnolinylene group), once substituted or unsubstituted exfoliation. Sitrate (丨11(132〇1716116运1'0叩), substituted or unsubstituted extended carbazolyl, substituted or unsubstituted phenazinylene group, substituted or unsubstituted a phenanthridinylene group, a substituted or unsubstituted pyranylene group, a substituted or unsubstituted chromenylene, a substituted or unsubstituted A benzofuranyiene group, a substituted or unsubstituted thiophene group (1^丨(^1161^16116 81'011卩), a substituted or unsubstituted benzothiophene group ( A benzothiophenylene group), a substituted or unsubstituted isothiazolylene group, a substituted or unsubstituted benzoin, a benzoimidazoly 1 ene group, and a substituted or unsubstituted The isoxazolylene group, but is not limited thereto. [0035] For example, each is a stupid base, a C,-C alkane 1 Q1 10 Q group, a styl group, a dialkyl group) Stretching phenyl, one (C6-C14 aryl) Base, one (two (C6-C14 aryl)) phenyl, one carbazolylene group, one (^-〇1 (), the base of the 0f sulphate, one or two (C, -C, n alkyl) An exocarbazolyl group, a CR-C" aryl carbazole group, a 1 IU 〇14 bis (Ce-C1yl aryl) carbazole group, a fluorenylene 6 14 group, a thiol thiol group, One or two (C^-C^o) bases, one (c6-c14 aryl) extended base, one (two (c6-c14 aryl) extended base, one naphthylene group, one Pyridyl-naphthyl, bis(qc^alkyl)-naphthyl, one (crc14 aryl)-naphthyl-100111378 Form No. A0101 Page 23/88 pages 1003273214-0 201204728, one-two (Ce-C1y) Aryl) anthranyl, anthranylene (14 group), one (^-(^)-based thiol-based, one-two-alkyl group), one (cs-c14 aryl) thiol group, one Di(c6-c14 aryl) anthracenyl, pyridinylene group, one (^-(:^alkyl-pyridylpyridyl, one-two (C-Cin alkyl)-extended pyridyl, one (C-C) The aryl group A 1 u 6 14 ) stretches more than the bite base, one or two (C6_C14 aryl). More than a bite base, a quinol iny lene group, a (^-(:1〇 alkyl quinolinyl, a dialkyl) quinolinyl group, a (c6-c14 aryl) stretching quinoline Base, one (two (C6_C14 aryl)) benzoyl, benzoimidazolylene group, one (^-(:^alkyl extended streptozolyl, one or two (C-C) based benzene And imidazolyl, a (c) 1 1 υ 6 14 yl) benzoimidazolyl group, a bis (c6-cu aryl) benzoimidazolyl group, an imidazopyrimidinylene group, an

Ci-C1Q alkyl extended imidazolium pyridyl, mono-(crCiQ alkyl) extended imidazolium pyridyl, mono(C^-C)4 aryl) extended imidazolium pyridyl, monodiaryl) Imidazopyrimidinylene group, one (: "(: burnt imidazolidine, 1-2 (crc1Q alkyl) imidazolyl pyridyl, one (CrCi4 aryl) imidazolyl pyridyl and / or one or two The imidazolidine group is, but is not limited thereto. [0036] For example, Ar, 11 Γ12 in the first substituent to the third substituent

Ari3, Ari5 and Aru may each be a hydrogen atom'--a hydrogen atom substituted or unsubstituted, a halogen atom, a thiol group, a cyano group, a fluorenyl C1_C30 alkyl group, a substituted or unsubstituted C -C substituted or unsubstituted C2 'block group, - taken 2 generations or unsubstituted 100111378 Form No. A0101 Page 24 / Total 88 Page 1003273214-0 201204728 Substituted c ~ c off its seven-one substituted or unsubstituted ^ ^ 5 30 soil 5 nWC3 ~ C3. Hetero square. For example, Ar

[0037] Ο, 1212, 讦13, and 訏16 may each independently be a hydrogen atom. A heavy wind atom is a self-priming atom, a thiol group, a —H group, a substituted or a 1 乂-substituted Cl_Cl oxime group, - substituted or unsubstituted c-based ... substituted or unsubstituted CrCi. Fast radical, _xin, J. substituted h, alkoxy, _substituted or unsubstituted C5 C14, and/or a substituted or unsubstituted %-heteroaryl, but not limited to this. In practice, Arn, Ar12, Ar13, Ari5, and Ari6 in the first to third substituents may each independently be a substituted or unsubstituted c"c3Q aryl group. For example, Ar,,, Ar, /Ατ. aa 11 12 Ari3 Ar15 and Ar16 can each be a hydrogen atom, a heavy hydrogen atom, a dentate atom, a hydroxy group, a cyano group, a fluorenyl group, an ethyl group, a propyl group, and a butyl group. Base, monopentyl, monovinyl, monopropenyl, monobutenyl, monopentenyl, monoethylidene, monomethoxy, monoethoxy, monopropoxy, monobutoxy, one a pentyloxy group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pentalenyl group, a substituted or unsubstituted indenyl group, once substituted or not Substituted naphthyl group, substituted or unsubstituted azulenyl group, substituted or unsubstituted heptalenyl group, substituted or unsubstituted benzo Indacenyl group, substituted or unsubstituted vinyl naphthyl (acenaphthyl gr Oup), substituted or unsubstituted fluorenyl group, substituted or unsubstituted 100111378 Form No. A0101 Page 25 of 88 1003273214-0 201204728 phenalenyl group, once substituted or not a substituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted unioranthenyl group, a substituted or unsubstituted group Triphenylenyl gr〇up, a substituted or unsubstituted pyronylenyl gr〇up, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted fused tetraphenyl Naphthacenyl gr〇Up, a substituted or unsubstituted plcenyl gr〇up, a substituted or unsubstituted perylenyl gr〇up, a substituted or unsubstituted pentaphenyl (pentaphenyl group), a substituted or unsubstituted hexacenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyridyl Group (pyr ^ zolyl group), a substituted or unsubstituted imidazolyl, (imidazolyl group), a substituted or unsubstituted flavor. An imidazolinyi group, a substituted or unsubstituted lmidazopyridinyl group, a substituted or unsubstituted imidazylpyrimidinyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted fluorenyl group, a substituted or Unsubstituted quinolinyl group, substituted or unsubstituted phthalazinyl group, substituted or unsubstituted indoli zinyl gr0Up, once substituted or not Substituted naphthyridinyl group, once substituted or unsubstituted 1001JI378 Form No. A0101 Page 26 of 88 Page 1003273214-0 201204728

The quinazolinyl group' - a substituted or unsubstituted cinnoliny 1 group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted anthracene An azolyl group, a substituted or unsubstituted Phenazinyl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted pyranyl group, once substituted Or unsubstituted chromenylene group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted thiophenyl group, once substituted or not Substituted benzothiophenyl group, substituted or unsubstituted isothiazolylene group, substituted or unsubstituted benzo. A benzothiopheny 1 group and/or a substituted or unsubstituted isoxazolyl group, but is not limited thereto. Ο For example, Arn, Ar12, Aru, Aru, and human 1*16 may each independently be a hydrogen atom, a heavy hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group, a monomethyl group, an ethyl group. , propyl, monobutyl, monopentyl, monovinyl, monopropenyl, monobutenyl, monopentenyl, monoethylidene, monomethoxy, monoethoxy, monopropoxy , monobutoxy, monopentyloxy, monophenyl, mono-, - (: nonylphenyl, di-(Ci_Ciq alkyl)phenyl, /(C6_C14 aryl)phenyl, one or two (C6 -Cu aryl)phenyl, monooxazolyl, mono-Cio-alkyl carbazolyl, mono-(CrC1G alkyl)carbazolyl, ^C6-CI4 arylcarbazolyl, one or two (C6-C14 Aryl) carbazolyl, monohydrazino, mono C1_C10 alkyl fluorenyl, mono-(C-Ci decyl) fluorenyl, a 100111378

Form No. A010I Page 27 of 88 1003273214-0 201204728 _C14^Base) fluorenyl, one (two (C6_C14 aryl) fluorenyl, one naphthyl, one

Naphthyl, pyridyl)naphthyl, mono(c6-ci4aryl)naphthyl, mono-(C6-C14 aryl)naphthyl, anthryl group, one (^-(^) Alkyl fluorenyl, bis(CrC1 decyl) fluorenyl, mono(c6-cu aryl) fluorenyl, mono-(crCi4 aryl) fluorenyl, monopyridyl, mono-quinolinyl, monoalkylpyridine Base, one or two ((: (1) alkyl) pyridyl, mono(c6-cl4 aryl)pyridyl, di-(c6-c14 aryl)pyridyl, monoquinolinyl, monoalkyl Quinolinyl, mono-dialkyl)quinolinyl, mono(c6-c14 aryl)quinolinyl, mono-((:6-(:14aryl)) fluorenyl, benzoimidazolyl Group), a Ci-Ciq mercaptobenzimidazolyl, monodialkyl) benzimidazolyl group, a (crcl4 aryl) benzimidazolyl group, a di(crc14 aryl) stupid Imidazopyridinyl group, decyl imidazolidinyl, monoalkylidene imidazolidinyl, mono(C-caryl)imidazolidinyl, mono-(c-C 0 14 6 14 aryl Imidazopyrididinyl group a base-based succinyl group, a succinyl group, a bis(crc1{)alkyl group), an imidazolyl group, a (c6-c14 aryl) imidazolidinyl group and/or a bis(cc aryl)imidazolidinyl group. c _c Examples of the fluorene group may include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and examples of the C5-C14* group may include a strepyl group, a naphthyl group, and an anthracenyl group, but are not limited thereto. For example, Arn, Ar12, Ar13, Arl5, and Ar16 may each be represented by any one of the following Formulas 4A to 4G: 100111378 Form No. A0101 Page 28/88 Page 1003273214-0 [0039] 201204728

Equation 4B

Formula 4A

Formula 4C

Formula 4D

Formula 4G

In Formulae 4A to 4G, Zi, Z2, Zn, and Z12 may each be independently, for example, a hydrogen atom, a heavy hydrogen atom, a monoalkyl group, a CfCn alkoxy group, and/or an L-Ch aryl group, p and q may each be an integer of 1 to 8, 〇14 and * is a bonding position with Ar, Ar, Ar, 八1'[; or 八1'<; When a is 0 in the first substituent, Arn may be represented by any one of the formulae 4A to 4G, and *4A to 4G is a bonding position of one of the ring atoms constituting the trunk of the formula 1, It is readily understood by those skilled in the art. [〇〇4〇] For example, Zi, z2, zn, and z12 may each independently be a hydrogen atom, a monohydric hydrogen atom, a monomethyl group, a monoethyl group, a monopropyl group, a monobutyl group, a monomethoxy group, Monoethoxy, monopropoxy, a phenyl, a naphthyl and/or a fluorenyl group [0041] For example, Ar, Ar, Ar1Q, Ar1c, and human 犷" may each be 11 11 13 15 16 by It is represented by any one of the following formulas 5A to 5E, but is not limited thereto: 100111378 Form No. A0101 Page 29 / Total 88 Page 1003273214-0 201204728 [0043] [0044] [0046] [0046] 100111378

Equation 5A

Equation 5D

Equation 5B Equation 5C

In the formula 5E, the term "*" in the formulae 5A to 5E is a bonding position with Ar, Αι·ζ, A%, a, or a%. For example, when a is 〇 in the first substituent, A]: n can be represented by any one of Formulas 5-8 to 5, * in the range of ^ to 5; which is the ring atom constituting the Si trunk. One of the bonding locations is readily understood by those skilled in the art. a, b, c, e, and f may each be an integer of one to one. For example, a, b, c, e, and f may each be 〇, i, 2, or 3, but are not limited thereto. When a = 0, the first substituent may be Al_ii, and 11 can be directly linked to the ring atom constituting the backbone of Formula 1. When a = 〇, the first substituent may be, for example, a substituted or unsubstituted ~?(10)aryl group or a substituted or unsubstituted crc3()heteroaryl group. For example, 'when b = G' a, where the second substituent can be directly linked to N ' is similar to the case when c, e, and f = 〇. d can be an integer from 1 to 1 〇. For example, d can be 1, 2, or 3, but is not limited to Form No. A0101 Page 30 / Total 88 Page 1003273214-0 201204728 Here. The second substituent and the third substituent - Ν[-(Αι·5), Αγ15][-(Α,)γΑΓι6] are each represented by any one of 6Α to 6Κ: Χ

In the formulas 6A to 6Κ, \ to 24 and Zu to Ζ14 may each be independently, for example: - a hydrogen atom, a - a heavy hydrogen atom, or one. An alkyl group (for example: -methyl, monoethyl, monopropyl, monobutyl and monopentyl), a c 1 10% sulfhydryl group (for example: monomethoxy, monoethoxy, monopropoxy) , —butoxy and monopentyloxy” and/or (6-(:14 aryl) (eg, a stupyl, a naphthyl, and a fluorenyl), p, q, r, and s may each be An integer from 1 to 8, * is a bonding position with A% or a ring atom of a constituent 丨 backbone. In practice, 'q can be an integer from 1 to 7, and 1* and 5 can be an integer from 1 to 4. [0048] In Formula 1, the group of _(Ar)_Ar of the first substituent

The la 11 J groups may be the same or different from each other; the "b" group of Ar2 may be the same or different from each other in the (Α『2)ι>_Α『ΐ2 group of the second substituent; the "c" group of Ar 3 may be the same or different from each other in the -(Ar3)c-Ar13S group of the second substituent; the "e" group of Ar in the -(A)_Ar group of the third substituent 5 e 15 100111378 No. A0101 Page 31 / 88 pages 1003273214-0 201204728: This same sound;, heart " matter "three-substance gas meter 6" factory 訏] 6 groups can be the same or different from each other. _9] [0050] ^佳地' 至少, at least - in the condensed cyclic compound is represented by the formula -::士:卜(Ar5)e_Ari5][-(α'Ά] (the first generation) Wherein d is an integer 1 phantom. Therefore, preferably, Ar is present in the condensed cyclic compound of the embodiment, that is, it is preferred that the backbone comprising the combination formula and formula 2 or the backbone system comprising the combination formula 1 and formula 3 is preferred. The ground is linked to the group indicated by the fiber 4 by -machi-"!*5)6士15]卜("6)厂八,]. The lack or deficiency of electrons can be achieved by the carbon position of the three stupid rings. The pre-P side, which is fused to the stem by Ar4, can prevent oxidation at the carbon position. Therefore, although the condensed ring 4-form compound represented by Formula 1 can be attacked by the nucleophile, The deterioration of the condensed cyclic compound can be substantially prevented. Therefore, an organic light-emitting device (OLED) comprising the condensed cyclic compound represented by Formula 1 can have improved effects such as current density, power, brightness, and lifetime. In Formula 1, R#Ri2 may be each independently, for example, a chlorine atom, a heavy hydrogen atom, a relatively atom, a -, a -cyano group, a first-substituted a base, a second substituent, and/or a third substituent; "a" in the first substituent is 〇 (ie, 'when any of rjr12' may be the first substituent, which may be directly linked to a constituent 1 The ring atom of the backbone); Wc may be 0 or 1 in the second 丄 1 generation; d may be 丨 or 2 in the third substituent, and "e" and the third substituent may each be 0 or 1; among the first substituent to the third substituent, each of which may be a substituted or unsubstituted C5-C14 aryl group or a substituted or unsubstituted C"C14 hetero aryl group And; among the first substituent to the third substituent, 14, 1 1 ΛΓ 1 〇 100111378 Form No. 101 0101 Page 32 / Total 88 Page 1003273214-0 201204728, Standard 13 士 15 16 can be individually, for example heavy a hydrogen atom, a halogen atom, a monohydroxy group, a ',, an unsubstituted W group, a substituted or unsubstituted::: or an alkenyl group, a substituted or unsubstituted c Ά 2 10 2 ι〇 block Or a substituted or unsubstituted w heteroaryl group. To 2 ^ can each independently is - C6-C14 aryl, substituted or unsubstituted.

For example, R^Ri2 may be independently a gas atom, a heavy gas atom, a single atom, a thiol group, a cyano group, a first substituent, a second substituent, and a third substituent; The substituent may be G; (4) each may be 0 or 1 in the second substituent; d may be 1 in the third substituent, and the third substituent may be independently 〇 or 1 in the third substituent. Between the first substituent and the third substituent, eight to eight can be each a phenyl group, a c _c 1 1 oxime base phenyl group, a bis (Cl-c10 wire) phenyl group, a (c6-ci4 aryl) group, a bis(C6-C14 aryl) group, a carbazolyl group, a C1 alkyl carbazole group, a bis(crCifl alkyl) carbazole group , a C6-Ci4 aryl extended carbazolyl group, a bis(Ce_Ci4 aryl) carbazole group, a stretching base, a (: plant (: 1 〇 alkyl thiol, a bis (Ci_ci 〇 alkyl) extension a group, a (C6_C14 aryl) fluorenyl group, a bis(C6-C14 aryl) fluorenyl group, a stilbene group, a (: plant (: 1 () alkyl-naphthyl group, a dialkyl group) Base, one (C6-C14 aryl) anthranyl, one or two (c6-c14 aryl) Naphthyl, a fluorenyl group, a Cj-Cu alkyl group, a bis((^-(:^)alkyl) group, a (C6-C14 aryl) group, a two (c6-c14) Aryl) fluorenyl, pyridine, monoalkylpyridyl, 1-2100111378 Form No. A0101 Page 33 of 88 1003273214-0 201204728 -ClQ alkyl) Pyridyl, one (C6-C14 aryl) a pyridyl group, a di-(Ce-Cu aryl)-extended pyridyl group, a quinolinol group, a Ci_Ci 〇 alkyl-extended quinolinyl group, a bis((^-(:丨^alkyl) quinolinyl group, a (CrCi4 aryl) quinolinolyl-di(c6-c14 aryl) quinolinol group, a benzzimidazolyl group, a Ci_Ciq alkyl-benzimidazolyl group, a dialkyl group , a (c6-c14 aryl) benzoimidazolyl group, a bis (C 6 - C1 4 square group) stupid and σ m ·» sit base, a stretch of taste. sit t (bite base, a CrC1G alkyl stretch Imidazolyl pyridyl, one (C C1G alkyl) ex-imidazole pyridyl, one (C6_C14 aryl) excimidazole pyridine group, one (two (C6-C14 aryl) imidazolidine pyridyl, one imidazolidinyl group, one Alkyl stretch imidazole shouting base, one by one a substrate, a (c aryl 1 1 υ 6 14 π group) imidazolidinyl group or a di-(c6-ci4 aryl) imidazolidine group; in the first substituent to the third substitution Among the bases, Ar, Ar, Ar, 11 12 13

Aris and Ar16 may each independently be a hydrogen atom, a monohydric hydrogen atom, a halogen atom, a monohydroxy group, a monocyano group, a monomethyl group, a monoethyl group, a monopropyl group, a monobutyl group, a pentyl group, an ethyl group. , a propyl group, a butenyl group, a pentenyl group, an ethyl fluorenyl group, a monodecyloxy group, an ethoxy group, a monopropoxy group, a monobutoxy group, a pentyloxy group, a phenyl group, a Ci_Cu alkylphenyl 'di(C1_C10 alkyl) phenyl, -(C6_C14 aryl) phenyl, -di(, _ c14 aryl) phenyl, monooxazolyl, a Ci_Cm alkylcarbazolyl , a two (crc1 () alkyl) carbazolyl group, a c6_ci4 aryl carbazolyl group, a di-(C6-Ci4 aryl) oxazolyl group, a fluorenyl group, a Ci_Cb alkyl fluorenyl group, a two (c丨-c1 〇alkyl)diyl, —(CrC]4 aryl)indenyl'-di((:6_ c14 aryl) 3⁄4yl, mononaphthyl, monoalkylnaphthyl, one or two ((^- Cioalkyl)naphthyl, mono(c-caryl)naphthyl, mono-(c _c b 4 6 14 aryl)naphthyl, monodecyl, mono-c-alkylalkyl, one-two (c _c 10011 】 378 i 1ϋ 1 10 1003273214-0 Form No. Α0101 Page 34 of 88 201204728 院Onion, a (rcc14 aryl) fluorenyl group, a bis(C6-C14 aryl) fluorenyl group, a pyridyl group, a crclG alkyl pyridyl group, a di(crc1Q alkyl group) pyridine group, a (C6 one C14 aryl)pyridyl, mono-(C6-C14 aryl)pyridyl, monoquinolyl, a crcifl alkylquinolinyl, mono-(c"Ci〇alkyl)quininyl, one (crc14-aryl)啥), 一 基, 一 (C6-C14 aryl) quinolyl, monobenzimidazolyl, monomethyl benzoimidazolyl, bis(CrCi 〇 alkyl) benzimidazolyl, (C6-C14 aryl) benzimidazolyl-(Cg-square) benzofuranyl group, one ° 嗤 ° ratio than a bite group, a Ci-C1G alkyl imidazolidinyl group, a di(C1_C1Q alkyl) imidazole Pyridyl, mono(CrCi4 aryl)imidazolidinyl, mono-(Ce-C1;)aryl)imidazole b 14 pyridyl, monoimidazopyrimidinyl, —Ci—Cb alkylimidazopyrimidinyl, mono-(CrCU)alkyl An imidazolyl group, a mono(C6-C14 aryl)imidazopyrimidinyl group or a mono(C6-C14 aryl)imidazolidine group, but is not limited thereto. [0052] 缩合 A fused cyclic compound represented by Formula 1 when it is carried out can Any one of the following formulas 2a to 2e are represented by the (formula i is " A " ring represented by Formula 2): 100 111 378 Page 35 Form Number A0101 / 88 Total 201 204 728 1003273214-0

Equation 2a

Equation 2b

Formula 2d In Formula 2a to Formula 2d, RJR19, Ar^Ar, Ar, Ar, 1 1 Z 1 0 1 1 \ 2 Ar13, Ar15, Ar16, a, b, c, d, e, and f may be as defined above . In Formula 2a to Formula 2d, A. It can be, for example, a stupid base, a c-c 4 1 phenyl group, a di-(crcl() alkyl group), a (c6-c14 aryl) phenyl group - a two (C6- C14 aryl) phenyl, oxazolyl, a q-ClG alkyl carbazole group, one (C plant CiG alkyl) carbazole group, - Ce-C 4 aryl carbazole group, one Di(c^Ch aryl) extended carbazolyl, — hydrazine group, a c plant, a hydrazide alkyl group, a bis (c "Ci 〇 alkyl"), a (C6-Cl4 aryl) Stretching base, a stretchy naphthyl group, a c ίο 100111378 bis(C6_C14 aryl) decyl 10 alkyl extended naphthyl group, a bis(CrC1Q alkyl group) stretching, a (C "C14 aryl" stretching naphthyl group ,-(C6-C14 aryl) extension 36 pages/88 pages Form No. A0101 1003273214-0 201204728 Ο Naphthyl, a fluorenyl group, a c1{) alkyl group, a bis (^ 乂 "alkyl group a thiol group, a (c6-c14 aryl) thiol group and a bis(C6-C14 aryl) thiol group, a stretch alpha ratio bite base, a C ^ - c μ burn base extension alpha ratio bite base, (C6-Ci4 aryl) extended pyridyl, mono-(C6-C14 aryl) extension ratio pyridine group, quinolinyl group, One (: plant (: 1 () alkyl quinolinolyl, one two ((: (1) alkyl) quinolinyl, one (C6-C14 aryl) quinolinyl, one or two ( (6-(:14-aryl) quinolinyl, benzoimidazolyl, a c1() alkylbenzimidazolyl, a bis(c^-Cualkyl)benzimidazolyl, one ( C6-c14 aryl) benzoimidazolyl, bis(c6-c14 aryl) extended benzimidazolyl, imidazolium pyridyl, one (: plant (: 1 () alkyl extended imidazolium pyridyl, one or two ( Ci-C^ alkyl) extended imidazolium pyridyl, monoaryl) imidazolidine, a ο14-4 aryl) 嗤 嗤 嗤 咬 、 、 、 、 、 、 、 、 、 005 005 005 005 005 005 005 005 005 005 005 005 005 005 005 a decyl imidazolidine group, a bis(C alkyl group) imidazolidinyl group, a (C6-C14 aryl) imidazolyl pyridyl group or a di(C6-C14 aryl) imidazolidine group. In the formula 2d, d may be 1, 2 or 3. For example, in the formula 2a to the formula 2d, 八1*4 may be a phenyl group and d may be 1 or 2, but the embodiment is not limited thereto. In Formula 2a to Formula 2d, -N[-( Ar ) of the third substituent represented by (Ar4)dN[-(Ar5)e-Ar15][-(Ar6)f-Ar16] -Ar 1 "fa , * η Ar15U-(Ar6)f-Ari6] can be represented by any one of Formulas 6A to 6K. [0055] In Formulas 2a to 2e, '', and each can be *, for example: - Substituent and "a" is Q in the first substituent. For example, in the formula, RlM8 may be the first substituent, "a" may be 第 in the first substituent, and 4 may be a substituted or unsubstituted 11~l14 square group or once Substituted or not 100111378 Form No. A0101 Page 37 / Total 88 Page 1003273214-0 201204728 丄 Substituted G3 Heteroaryl. In detail, in Equations 2a to 2e,

Ri and % can be individually, for example: a stupid base. In the formula 2d, '% may be a first substituent, and, in the case where the first substituent may be 〇+, in the formula 2d, % may be the first substituent," a„ The substituent may be hydrazine, and may be a substituted or unsubstituted Cs Cu aryl group or a substituted or unsubstituted heteroaryl group. In detail, in Formula 2d, \ and 1-8 may each be It is a phenyl group. The condensed cyclic compound represented by Formula 1 may be represented by any of the following Formulas 3 & to 3e:

'1?, to 1?10, Ai^, Ar1t} ' in Equations 3a to 3e

1 iI 1 ο 11 i L

Ar13, Arl5, Ar16, a, b, c, d, e and f can be as defined above. In Formulae 3a to 3e, Ar4 may, for example, be a phenyl group, a Ci-C^ phenyl group, a hexa(crcl{)alkyl group), a phenyl group, a (c6-c14 aryl) phenyl group, 100111378 Form No. A0101 Page 38 / 88 pages 1003273214-0 [0058] 201204728 One (C6-C14 aryl) stretch phenyl, one stretch. Carboxy, a Ci-Cu-based carbazolyl, a bis ((: (1) alkyl) carbazole group, a C6-C14 aryl group. 圭 基, 一二 (C6_C14 aryl ) 嗤 嗤 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , Aryl) anthracenyl, an extended naphthyl group, a monoalkylnaphthyl group, a di(Ci-C1Q alkyl) anthranyl group, a (C6_C14 aryl) anthranyl group, a bis(C6-C14 aryl) group Naphthyl, anthracene, hydrazine, hydrazine, hydrazine, hydrazine, hydrazino, hydrazino, hydrazino, hydrazino Di(c6-c14 aryl) thiol group, one extension ratio than bite base, one base extension ° bite base, one (, - (: 14 aryl) extension. than bite base, one or two (c6-c14 aryl Stretching "pyridyl, a quinolinyl, a C1_C1Q alkyl quinolinyl group, a bis(h-Cu alkyl) quinolinyl group, a (crc14 aryl) quinolinyl group, a two (c6) -c14 aryl) quinolinyl, benzoimidazolyl, monoalkylbenzimidazolyl, hexa(crc1Q alkyl) Stupid imidazolyl, mono(C6-C14 aryl)-benzimidazolyl, mono-(C6-C14 aryl)-benzimidazolyl, imidazolidinylpyridyl, monoalkylexidazolidinyl, monoalkyl An imidazolidine pyridyl group, a (C6-C14 aryl) extended imidazolium pyridyl group, a di-(C6-C14 aryl) exemplified by a bite base, a stretched σ meter spit bite base, a q-Cio alkyl stretch Imidazopyrimidinyl, monodialkyl)imidazolidinyl, mono(C-Caryl)thidium imidazolyl or bis(c-Cuarylυ1^ 614) an imidazolidine group. In Formula 3a to Formula 3e In the formula 3a to the formula 3e, the person 1"4 may be a phenyl group and d may be 1 or 2, but the embodiment is not limited thereto. 0059] 100111378 In the formula 3a to the formula 3e, N[(Ar5)e-Ar15] [_(3) of the third substituent represented by 1003273214-0 Form No. A0101 Page 39/88 page 201204728)f-Ar16] Ar6)f-Ar16] may be represented by any one of Formulas 6A to 6K. In Formulae % to 3 (1, \ and , each may be, for example, a first substituent, and "a" In the case of a substituent, it is 〇. For example, In the formulae 3a to 3d, R and may each be a first substituent, "a" may be a hydrazine in the substituent, and Au may be a substituted or unsubstituted c$_Cu aryl group and/or A substituted or unsubstituted \_Ci4 heteroaryl group. In detail, in the formulae 3a to 3d, \ and 1?3 may each be a stupid base. [0060] In Formula 3e, for example, a first substituent may be used, and "a" may be 0 at the first substituent. For example, in Formula 3e, 'which may be the first substituent, "a" may be 〇, and may be a substituted or unsubstituted C5_Cu aryl group and/or substituted or Unsubstituted C heteroaryl JL,, 3 14 , in detail, in Formula 3e, \ and % may each be a phenyl group. In the implementation, the condensed cyclic compound represented by Formula 1 may be the following Compounds 1 to 27, but is not limited thereto: 100111378

Formula 1

Form number A0101

Equation 4 Page 40 of 88 1003273214-0 201204728

Equation 9

100111378 Form No. A0101 Page 41 of 88 1003273214-0 201204728

ό 15

Equation 19

100111378 Form NumberΑ0101 Page 42/Total 88 Page 1003273214-0 201204728

Ο [0062]

案例 Examples of the unsubstituted group used hereinafter may include methyl group, ethyl group, propyl group, isobutyl group, secondary butyl group, pentyl group, isopentyl group, hexyl group, and the like. After the replacement. The alkyl group, as described above, of the unsubstituted C-C alkylene 25, at least one hydrogen atom of the hydrazine, long i sinkyl group may be, for example, a heavy hydrogen atom, a self atom, an atom, a nitro group, a cyano group, or Amino, methyl lung, hydrazine, knee, 1 base or a salt thereof, a bis or a salt thereof, a monophosphoric acid or a salt thereof, a W group, a -Crc3. Alkenyl, a c2_c30 alkynyl, a c6-c3 aryl, a v, a heteroaryl, _Ν (ν(ν or _Si(V(V(V, where 1 gas may each be a hydrogen atom, - a heavy hydrogen atom, a silk, a dilute group, a W aryl group, and a -c2-c2G heteroaryl group. The substituted or unsubstituted w-extension group may be, for example, a structure having the structure described above. Substituting the silk by the langxian phase (10) divalent linking group 100111378 The unsubstituted alkoxy group may be a group represented by _0A, wherein A is an unsubstituted Ci_c pentane group as described above. Substitute Form No. A0I01 Page 43 / Total Ribs 1003273214-0 [0063] Examples of 201204728-c3() alkoxy groups may include monomethoxy, monoethoxy and isopropoxy. At least one hydrogen atom The alkoxy group may be substituted by a substituent as described above, together with a substituted alkyl group. [0064] The unsubstituted C2_C3() alkenyl group may have a carbon-carbon double bond at the center or The terminal hydrocarbon chain of the unsubstituted c2-c3() alkyl group. Examples of the alkenyl group may include a monovinyl group, a propylene group, a butenyl group, and the like. At least one hydrogen atom is not present. The substituted (:2-(:3{) alkenyl group may be substituted by the substituted (^-(:3()) alkyl group. The substituted or unsubstituted alkenyl group may be a structure with the above described

L ϋ U A substituted or unsubstituted C2-C3() alkenyl group having the same divalent linking group. [0065] The unsubstituted c9-cqn alkynyl group can be at least one carbon-carbon having a center

u ϋ U triple bond or the hydrocarbon chain of the terminal of C2-C3() alkyl. Examples of the unsubstituted C2-C2() alkynyl group may include an ethynyl group, a propynyl group, an analog thereof, and the like. At least one hydrogen atom in the alkynyl group may be substituted with the above substituents, together with the alkyl group. The unsubstituted CR-CQn# group may be a mono 5 30 valent group having a carbocyclic aromatic system having 5 to 30 carbon atoms containing at least one aromatic ring. Unsubstituted CK-CQn extended aryl group can be a carbon ring aromatic

ο 〇 U The divalent group of the aromatic system having 5 to 30 carbon atoms containing at least one aromatic ring. When the aryl group and the extended aryl group have a bicyclic ring, they may be fused to each other. The at least one hydrogen atom at the aryl group and the extended aryl group may be substituted with the above substituents, together with the CfCM alkyl group. [0067] Examples of the substituted or unsubstituted L-Cm aryl group may include a phenyl group,

b 〇U a (^-(:1() alkylphenyl (for example: monoethylphenyl), one (^-(:1()) alkyl 100111378 Form No. A0101 Page 44 / Total 88 Page 1003273214- 0 201204728 Q diphenyl (for example: monoethyldiphenyl), - by phenyl (for example: an ortho, meta or parafluorophenyl and diphenyl), dicyanophenyl, a Trifluoromethylphenyl, an ortho, meta or para-p曱lyl group, an ortho, meta or para cumenyl group, xylyl Group), _ phenyloxyphenyl, mono(α,α-xylene)phenyl, —(N,N,-dimethyl)aminophenyl, —(N,N-phenyl)amino Phenyl, pentalenyl group, monodecyl, mononaphthyl, mononaphthyl (eg, -fluoronaphthyl), -crc1Gmorphinyl (eg, monomethylnaphthyl) , a Ci_Cio oxynaphthyl group (for example: -methoxynaphthyl), - fluorenyl, -founding, - and cycloheptyl, naphthyl, ..., aryl, - fluorenyl ,-methylmercaptophenylidene, tris-decyl, -normyl, -m,-ethyl-child,-based One recorded, monochlorofilament, -pentaphenyl, -pentaphenyl, -tetraphenyl, hexaphenyl, hexaphenyl, rubicenyl gr〇up, hexamethylene (C〇r〇nenyl group), - a stretched trinaphthyl group, a fused heptaphenyl group, a fluorene-isohexaphenyl group, a -pyrythrenyl gr. and/or an ovalenyi group. Examples of substituted (:5-(:3())aryl groups can be inferred based on the upper and lower substituted CrC3 fluorenyl groups. Examples of substituted or unsubstituted c"c(9) extended aryl groups It can be inferred based on a substituted or unsubstituted c-c aryl group. 5 〇〇 [0068] The unsubstituted C3-C3 doped aryl group may be a monovalent group having at least one aromatic ring. At least one hetero atom comprising at least one of nitrogen, gas, phosphorus and sulfur. The unsubstituted [-(:(9) heteroaryl group may be a divalent group having at least one aromatic ring] The aromatic ring has at least one impurity 100111378 Form No. A0101 Page 45 / Total 88 Buy 1003273214-0 201204728 Atom, read heteroatoms containing, for example: nitrogen, oxygen, phosphorus and sulfur. When the heteroaryl group and the heteroaryl group have at least two rings, they may be fused to each other. At least one hydrogen atom may be substituted by the above substituent in the heteroaryl green heteroaryl group together with the crc3. Examples of non-, star-substituted C; TC3()heteroaryl groups may include a pyrazolyl group, an imidazolyl group, an oxazolyl group, a thiazolyl-triazole. Base, one tetrazolyl group. Sitrate, oxime ratio <yl, taphthyl gr〇up) pyrimidinyl, monomorphyl, monooxazolyl, monodecyl, monoquinolyl, isoquinolyl, monobenzo Imidazolyl, monoimidazolidinyl and/or one meter saliva. The unsubstituted c", heteroaryl group can be inferred based on the substituted or unsubstituted c6-c3() extended aryl group. The condensed cyclic compound of the formula 1 can be synthesized by using organic synthesis. The method of the cyclic compound can be based on an example to be discussed later. The condensed bad compound of Formula 1 can be used for an organic light-emitting device. According to another embodiment, the organic light-emitting device can include a first electrode, a first The two electrodes are disposed between the first electrode and the second electrode with respect to the first electrode and the first layer, wherein the first layer comprises the condensed cyclic compound of the above formula i. The first layer may be an electric , but not limited to, a hole transport layer, a hole injection layer, a functional layer having a hole injection function and a hole transfer function, an emission layer, an electron transport layer, and an electron injection layer For example, the first layer can be a hole transmission layer, a hole injection layer, a functional layer having a hole injection function and a hole transfer function, and a 100111378 form number A0101 page 46/ A total of 88 pages 1003273214-0 201204728 shot In addition, according to a structure in which an organic light-emitting device can be embodied, various known layers can be used as the first layer. [0073] FIG. 1 illustrates an organic light-emitting device according to an embodiment. A cross-sectional view of an OLED) 10. Hereinafter, a method of fabricating an organic light-emitting device according to an embodiment and an organic light-emitting device according to an embodiment will now be described with reference to Fig. 1. [0074] Ο Referring to FIG. For example, the organic light-emitting device 10 can include a substrate 11, a first electrode 13, an organic layer 15, and a second electrode 17, which are sequentially stacked in this order. The substrate 11, which can be used for a conventional organic light-emitting device Any suitable substrate may be, for example, a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, penetration, surface smoothness, ease of handling, and water resistance. [0075]

The first substrate 13 may be, for example, deposited or sputtered with a material for forming the first electrode 13 on the substrate. When the first electrode 13 constitutes a positive level, the material for forming the first electrode 13 may be a high work function material to facilitate hole injection. The first electrode 13 can be a reflective electrode or a transmission electrode. A transparent and electrically conductive material such as indium tin oxide (iridium), indium zinc oxide (niobium), tin dioxide (Sn〇2), and zinc oxide (?n) can be used to form the first electrode 13. The first electrode 13 can be used as a reflective electrode, for example, magnesium (Mg), Ming (Α1), ίLu-Li (Al-Li), about (Ca), magnesium-indium (Mg-Ιη), and silver (Mg) -Ag) or other analogs and the like. The organic layer 15 may be disposed on the first electrode 13. The term "organic layer" is used hereinafter to mean that either one of the first electrode 13 and the second electrode 17 is interposed. The organic layer 15 may not be formed of a pure organic material, and may also include: 100111378 Form No. A0101 Page 47 of 88 1003273214-0 [0076] 201204728 For example, a metal composite. [0080] The organic layer 15 may comprise a first layer comprising a condensed cyclic compound of the formula 。. The organic layer can further include a hole injection layer (HIL), a hole transfer layer (HTL), a functional layer having a hole injection function and a hole transmission function, an emission layer, and a hole blocking. At least one of a layer (HBL), an electron transport layer (ETL), and a germanium electron injection layer (EIL). For example, the first layer is a germanium hole transport layer, and the organic layer 15 is in addition to the first layer. The method further includes a hole injection layer, an emission layer, an electron transport layer, and an electron transfer layer, but is not limited thereto. The hole injection layer <transmission, for example, vacuum deposition, spin coating, burning Casting, Langmuir-blodgett (LB) deposition or the like is formed on the first electrode 13. When the hole injection layer is formed by vacuum deposition, vacuum deposition conditions can be used according to The compound forming the electric sea injection layer and its desired structure and the thermal properties of the hole injection layer are changed. For example, the vacuum deposition may be at about 1 Torr. (: to a temperature of about 5 〇 0 ° C, approximately a pressure of from 1 〇 8 to about 10 _ 3 Torr, and a deposition rate of about 100 angstroms per second However, the deposition conditions are not limited to this. When the main hole of the hole is formed by spin coating, the coating conditions may be based on the compound used to form the hole layer and the desired structure and hole injection layer. The thermal properties vary. For example, the coating rate can range from about 2000 to 5000 rpm, and after a range of from about 80 t to 200. (A range of coatings, heat treatment is performed to remove a solvent. The coating conditions are not limited thereto. 100111378 Form nickname A0101 Page 48/88 page 1003273214-0 201204728 [0081] The hole injection layer may be formed of at least one condensed cyclic compound represented by Formula 1, and any suitable The materials may be used collectively to form a hole injection layer. Examples of known materials that may be used to form the hole injection layer may include, but are not limited to, Ν, Ν'-diphenyl-Ν, Ν'-double -[4-(Phenyl-m-nonylphenyl-amino)-phenyl]-diphenyl-4,4'-diamine (DNTPD), phthalocyanine compound, for example: copper phthalocyanine ), Ο 4, 4', 4' ginseng (3-methyl phenylamino) triphenylamine (m -MTDATA),Ν,Ν'-bis(1-naphthyl)-N-N'-diphenylbenzidine (NPB), TDATA, 2T-NATA, polyaniline/dodecylbenzenesulfonic acid (dodecy1 benzenesulfonic Acid, Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PED0T/PSS), polyaniline/camphorsulfonic acid (pani/cSA) and polyaniline/poly(4-styrene sulfonate (pani/pss)) »

[0082] The thickness of the hole injection layer may be, for example, about 100 angstroms to about 1,000,000 angstroms. Maintaining the thickness of the electrical entry layer is approximately 100 angstroms to 1 〇. _Eco helps to confirm that the hole's master layer has excellent hole injection capability when there is no substantial increase in drive voltage. In practice, the thickness of the hole injection layer can be, for example, from about 1 angstrom to about 1,0 angstrom. Then 'the hole transmission layer is permeable, for example: vacuum deposition, spin coating, burnt, Langmuir_bi〇dgett, (8) 100111378 Form No. A0101 Page 49 / 88 pages 1003273214-0 [0083] 201204728 deposition or other manner is formed on the hole injection layer. When the hole transport layer is formed by vacuum deposition or spin coating, although conditions for deposition and coating may be used to form a hole injection layer The material is changed, and the conditions for deposition or coating may be similar to the conditions for forming the hole injection layer. [0084] The hole transport layer may include, or may be formed of, a condensed cyclic compound represented by the above formula 1. The first layer of the condensed cyclic compound represented by Formula 1 may be a hole transport layer. If the first layer is not a hole transport layer, the hole transport layer may be formed using any suitable hole transport material. Examples of the hole transporting material may include: a 圭 圭 derivative, for example: N-phenyl odor or ethylene group. Card β sitting; an amine derivative having an aromatic ring, such as shown below :Ν,Ν'-double (3- Phenyl)-fluorene, Ν'-dimercapto-[1,1-dimethyl]_4,4'-diamine (TPD); and monotrimethylamine-based materials, for example: 4, 4', 4' '-Find (Ν-carbazolyl) tridecylamine (TCTA). In these materials, TCTA can not only transmit holes, but also inhibit excitons from diffusing into the emissive layer.

[0085] The hole transport layer may have a thickness of from about 50 angstroms to about 1,000 angstroms. Maintaining the hole transport layer thickness from about 50 angstroms to about 10,000 angstroms helps to confirm that the hole transport layer has excellent hole transport capability when there is no substantial increase in drive voltage. When implemented, the hole transport layer can be, for example, from about 100 angstroms to about 800 angstroms. [0086] Alternatively, it has a hole injection function and a hole transmission function. 100111378 Form No. 1010101 Page 50/88 Page 1003273214-0 201204728 The layer can be formed not by the hole injection layer and the hole transmission layer. The functional layer can be formed from a known material to form a functional layer. [0087] at least one of the hole injection layer, the hole transport layer, and the functional layer may further include a charge generating material to improve conductivity of the layer, except for the condensed cyclic compound of Formula 1, which is known for The hole is injected into the layer, and this known material is used for the hole transport layer.

[0088] The G charge generating material may be a p-dopant. Examples of the p-dopant include, without limitation, an anthracene derivative such as tetracyanoquinone dioxane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4- Benzacene 0 if dioxin (F4TCNQ); oxidized metals such as: tungsten monoxide and molybdenum monoxide; and a cyano group-containing compound represented by the following compound 100, but not limited thereto:

[0090] 100111378 Compound 100 When the hole injection layer, the hole transport layer or the functional layer further contains a charge generating material, the charge generating material may be homogeneously or non-uniformly dispersed in the hole injection layer , hole transport layer or functional layer. Next, the emissive layer can be formed on the hole transport layer or the functional layer by utilizing, for example, vacuum deposition, spin sputtering, firing, LB deposition, or the like. When the emissive layer is formed by vacuum deposition or spin coating, although the conditions of deposition and coating may be changed according to the material used to form the emissive layer, Form No. A0101, page 51 / 88 pages 1003273214-0 201204728 change, deposition and coating The cloth condition can be similar to the conditions for forming the hole injection layer. [0091] The emissive layer can be formed from at least one of the fused cyclic compounds of Formula 1 and any suitable luminescent material (including both a host agent and a dopant). Examples of the main agent may include Alq3, 4, 4'-N, Ν'-di-ca-ca-diphenyl (CBP), poly(η-ethylene-based saliva) (PVK), 9, 10-two (萘Naphthalene-2-yl)anthracene (ADN) 'TACA, 1,3, 5-paran (N-phenylphthalimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di - 3-tert-buty 1-9, l〇-di-2-naphthyl anthracene (TBADN), E3, and dipyryl vinyl styrene (DSA), but are not limited thereto.

PVK AND

Examples of suitable red dopants may include: PtOEP, Ir(piq)3#, and Btp2Ir(acac), but are not limited thereto. 100111378 Form No. A0101 Page 52 of 88 1003273214-0 201204728

Examples of suitable green dopants may include: Ir(ppy) 3 (ppy = phenyl mouth bite), Ir (ppy) (acac), and Ir (mpyp), but are not limited to L «5 .

[0094] Examples of suitable blue dopants may include: F2Irpic,

(卩2??7) 211' (seven 111 £1), 11' ((1[??2)3, third-苐, 4,4'-bis(4-diphenylaminostyryl) ) is a combination of DPAVBi and 2,5,8,11-tetra-tert-butylphenyl, but is not limited thereto.

DPAVBi Page 53 of 88 TBPe Form No. A0101 1003273214-0 201204728 [0095] When the emissive layer comprises a main agent and a dopant, the weight of the dopant is based on the weight of the main agent of 100 parts. It may be from about 0.01 to 15 parts, but is not limited thereto. [0096] The emissive layer may have a thickness of from about 100 angstroms to about 1,000 angstroms. Maintaining the thickness of the emissive layer from about 100 angstroms to about 1,000 angstroms can help confirm that the emissive layer has excellent illuminating power when the driving voltage is not substantially increased. In practice, the thickness of the emissive layer can be, for example, from about 200 angstroms to about 600 angstroms. [0097] When a fluorescent dopant is also used to form the emissive layer, a hole blocking layer can be formed in the hole by utilizing, for example, vacuum deposition, spin coating, firing, LB deposition, or the like. Between the transmission layer and the emission layer to prevent triple excitons or holes from diffusing into the hole transport layer. When the hole blocking layer is formed by vacuum deposition or spin coating, although the conditions of deposition and coating may vary depending on the material used to form the hole blocking layer, the conditions of deposition or coating may be combined with the formation of the hole injection layer. The conditions are similar. Any suitable material that is commonly used to form the barrier layer of the hole can be used. Examples of the material for forming the hole blocking layer may include a oxadiazole derivative, a triazole derivative, and a morphine (mouth 11211 &111; 111'〇1丨116) derivative, but are not limited thereto. . [0098] The hole barrier layer may have a thickness of from about 50 angstroms to about 1,000 angstroms. In practice, the thickness of the barrier layer can be, for example, from about 100 angstroms to about 300 angstroms. Maintaining the thickness of the hole barrier layer from about 50 angstroms to about 1,000 angstroms can help confirm that the hole barrier layer has excellent hole blocking capability without substantially increasing the drive voltage. [0099] Next, an electron transport layer is permeable, for example, vacuum deposition, rotation 100111378 Form No. A0101 Page 54 / 88 pages 1003273214-0 201204728 Coating, burning tungsten or the like is formed in the hole blocking When the w electron transport layer on the layer or the emissive layer is formed by vacuum deposition or spin coating, the conditions of ... and / or the coating may be changed according to the material used to form the electron transport but the conditions of deposition and coating may be The condition a of forming the hole injection layer is similar. The material used to form the electron transport layer may be a material that stably transports electrons, which may be injected by an electron injecting electrode (cathode), and any suitable material may be used. Examples of the material forming the electron transport layer may include a phthalocyanine derivative, for example, ginseng (8-quinoquinone) alumnium * Alq3) 'TAZ > BAlq and bis(benzene And quinoline _i〇_oleic acid) wrinkle (Be), but not limited to this

[0100] The thickness of the electron transport layer may be, for example, about 100 angstroms to 1,000 angstroms. The thickness of the electron transport layer may be, for example, about 150 angstroms to 500 angstroms. Maintaining the thickness of the electron transport layer at about 100 angstroms to 1,000 angstroms helps to confirm that the electron transport layer has satisfactory electron transport capability without substantially increasing the driving voltage. Still alternatively, the electron transport layer may comprise an electron transporting organic compound and a metal containing material. Examples of the electron transporting organic compound may include, without limitation, AND(9, 10-bis(naphthalen-2-yl) onion) and onion-based compound represented by the following compound 101 or 102, but are not limited thereto. 100111378 Form No. A0101 Page 55 of 88 1003273214-0 201204728

Compound 101 Compound 102 [0102] The metal-containing material may comprise a one-in-one composite. An example of this bell complex includes, in an infinitely limited form, compound 10 3 of lithium quino late (Li Q) or below. [0103]

Compound 103 Next, an electron injection layer may be formed on the electron transport layer. The electron injecting layer can be formed of any suitable material that facilitates electron injection from the cathode. Examples of the material for forming the electron injecting layer may include lithium fluoride, sodium chloride, fluorinated planer, lithium oxide, and cerium oxide. Although the conditions of deposition and coating may vary depending on the material used to form the electron injecting layer, the conditions of deposition and coating of the electron injecting layer may be similar to those for forming the hole injecting layer. [0106] Thickness of the hole injecting layer It can be from about 1 angstrom to about 100 angstroms. Maintaining the thickness of the electron injecting layer from about 1 angstrom to about 100 angstroms helps to confirm that the electron injecting layer has a satisfactory electron injecting ability when the driving voltage is not substantially increased. In practice, the thickness of the electron injecting layer may be, for example, about 3 angstroms to about 90 angstroms 100111378. Form No. A0101 Page 56 / Total 88 pages 1003273214-0 201204728 ο [0107] Finally, the second electrode 17 may be disposed in an organic On layer 15. The second electrode 17 may be a cathode which is an electron injecting electrode. A metal forming the second electrode may be a metal having a low power, an alloy having a low power, an electrically conductive compound or a mixture thereof. In this regard, the second electrode 17 may be, for example, lithium (Li), magnesium (Mg), aluminum (Α1), aluminum (Α1)-lithium (Li), calcium (Ca), lock (Mg)-indium (In ), a town (Mg)-silver (Ag) or the like, and a transfer electrode which can be formed into a film type. In practice, the transfer electrode may be formed of, for example, oxidized oxalate (ITO) or indium zinc oxide (ITO) to produce a top emission type light-emitting device. When the first layer in the organic light-emitting device is a hole injection layer, a hole transport layer or a functional layer, in addition to the condensed cyclic compound of the above formula 1, the first layer may further contain the above-described charge generating material. Alternatively, when the first layer is an emissive layer, in addition to the condensed cyclic compound of Formula 1, the first layer may further comprise the above-described fluorescent dopant. As such, the first layer is not limited to the above. [0109] Hereinafter, one or more embodiments will be described in more detail in conjunction with the following examples. These examples are not intended to limit the purpose and scope of one or more embodiments. Example 忐 忐 实 实 实 实 实 实 实 实 实 实 实 . . . . . . . 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物

E F

B 1,4-cyclohexanedione of Compound B: 3.4 g (0·31 mol), 90 g (0.62 mol) of phenylhydrazine·hydrochloric acid and 1 ml of acetic acid in 1 liter A round neck flask was charged with 60 ml of ethanol. This mixture was heated at 50 ° C for 1 hour and cooled to room temperature. The resultant solid was filtered, washed with ethanol several times, and dried under vacuum to collect 73 g of a pink compound a in a yield of 80%. 600 ml of acetic acid and 120 ml of sulfuric acid were placed in a 5 liter round neck flask and cooled in an ice bath. 217. 5 g (0.74 mol) of compound a was added to the resulting mixture and stirred vigorously at Ot: for 10 minutes. The ice bath was removed and the resulting mixture was stirred at room temperature for 10 minutes. Next, the resulting mixture is heated by a heating pack. Heating was stopped at about 45 ° C and the resulting mixture was stirred. When the resulting mixture was stable, it was slowly cooled to room temperature and stirred at room temperature. The resulting solid was filtered, washed in the order of acetic acid, water, and diethyl ether, and dried under vacuum to yield 51 g of compound b. 100111378 Form No. A0101 Page 58 of 88 1003273214-0 201204728 [0112] !Η NMR (300MHz, DMSO-d6) 5 11.01 (2H), 8.19 (2H), 8.10 (2H), 7.45 (2H), 7.36 (2H), 7.12 (2H). [0114] Synthesis of hydrazine c. 30 g (0.1117 mol) of compound b was mixed with 1 liter of i,2-dibenzene to obtain a mixture. 6克(3当ΐ), 6.2 g (2. 2 eq.) of 18-crown-6, 129. 5 g (8 equivalents) of carbonic acid, 29.8 g (4 equivalents) of copper, and 99.4 g (3 ΐ) The bromine was added to the mixture and heated to a temperature of 180 °C. This resulting mixture was maintained at a temperature of about io 7 Torr to about i8 (rc for two days to obtain a mixture. Then 'the resulting mixture was cooled to room temperature, and when filtered with a silicone pad' was washed several times with toluene. This filtered solution was concentrated. The product was added to the filtered solution to precipitate a solid, and then the precipitated solid compound was filtered. The resulting mixture was washed with ethyl acetate and dried under vacuum to give 14.4 g, yield 21 7% of compound C. NMR (300MHz, DMSO) δ 8.31 (2Η), 8.21 (2Η), 7.90 (6Η), 7.72 (4Η), 7. 40 (4Η), 7.24 (2Η). [0115] The compound Ϊ) is combined with 4. 08 g (10 mmol) of compound C to 80% acetic acid (100 ml)' then 1.357 g (5. 35 mM) of iodine (12) and 0.333 g. (1.46 mmol) of solid periodic acid (ΗΙ〇) was added to the aforementioned mixture. 〇 6 This mixture was then stirred under a nitrogen atmosphere at 80 ° C for 2 hours. After the reaction was completed, the reaction product was extracted three times with 50 ml of dioxane to collect the organic layers. The organic layers were dried over magnesium sulphate and evaporated to a residue of 100111378 Form No. A0101, page 59 / 88 pages 1003273214-0 201204728. The residue was separated and purified using a silica gel column chromatography to afford 6.14 g, yield 87% of Compound D. [0116] H NMR (300MHz, DMSO) 5 8.28 (1H), 8.25 (1H), 8.Q6 (1H), 7.90-7.86 (6H), 7.71 (4H), 7·38-7.32 (4H), 7.21 (2H). Compound F 厶忐 5.34 g (10 mmol) of compound D, 0.5 mmol of [ι, Γ-bis(diphenylphosphino)ferrocene] dichloropalladium (π) ): palladium dihydrate (dppf), 2. 66 g (10.5 mmol) of bis(pinamic acid) diboron and 3.92 g of potassium acetate added to 200 ml of dimethyl sulfoxide (DMS0), and mixed at 90 ° C for 6 hours under a nitrogen atmosphere. The resulting mixture was cooled to room temperature and then placed in 300 ml of water to form a white precipitate. The white precipitate was filtered, and then dried under reduced pressure to yield 4.65 g, yield 87% of Compound E. Compound E was dissolved in 150 ml of toluene, 2.46 g (8.7 mM) of bromo-4-iodobenzene, 200 mg (2 mol%) of ruthenium (trimethylphosphane) palladium (〇) ): (triphenylphosphine) 4, and 2.4 g (17.4 mmol) of aqueous potassium carbonate solution were added to the resulting mixture. After maintaining the resulting mixture for 6 hours at 8 ° C, the reaction product was extracted three times with 50 ml of dichloromethane to collect the organic layers. The organic layers were dried over magnesium sulfate and the residual solvent was evaporated. The residue was separated and purified by a silica gel column chromatography to obtain 6.2 g of a compound F of a yield of 79%. 100111378 ]H NMR (3〇〇MHz, DMSO) ά 8.25 (1H), 8.17 OH), 8.10 (iH), 7.99 (2H), 7.95-7.87 (5H), 7.83-7.80 (6H), 7 76-7. 72(4H), 7. 70-7. 58(3H) Form Sfe A0101 Page 60 of 88 Stomach 1003273214-0 201204728 [0119] Compound 1 is a compound that passes through the following reactions. Process lb synthesis: Reaction process lb

NaOffiu

化合物 Compound I 3 3 g (5.32 mmol) of compound F and 1.08 g (6.38 mmol) of diphenylamine were dissolved in toluene and 97.4 mg under a nitrogen atmosphere ( 〇. Π 莫 )) 参 (dibenzylideneacetone) dipalladium: Pd (dba) and 22 2 3

G mg (0·11 mmol) of tris(t-butyl)phosphine was added to the aforementioned mixture. Then, 1.62 g (15·96 mmol) of NaOBu was added to the resulting mixture, followed by stirring at 80 ° C for 4 hours. The resulting mixture was cooled to room temperature and extracted three times with di-methane to collect organic layers. The organic layer was dried over magnesium sulfate, and the residual solvent was evaporated, and the residue was purified and purified by silica gel column chromatography to obtain 2.6 g of Compound 1 in a yield of 76%. !H NMR (300MHz, DMSO) δ 8.25(1H), 8.14(2H), 8. 06(1H), 7. 97(2H), 7. 88-7. 79(1 1H), 7. 73(2H), 7. 58-7. 41 (6H), 7.37(2H), 7.24(2H), 7.08-6.96(4H). Example 2: Compound 3: Compound 3 was synthesized by the following Reaction Scheme 2: 100111378 Form No. A0I01 Page 61 of 88 1003273214-0 201204728 Reaction Scheme 2

Compound 3 3 g (5. 32 mmol) of compound 1? and 2 31 g (6 38 mmol) of amine compound were added to toluene, and then 97.4 mg (0. 11 mils) under a nitrogen atmosphere. Moss (dibenzylideneacetone) dipalladium: pd^dba) 3 & 22 mg (0.11 mmol) of tris(t-butyl)phosphine was added to the aforementioned resulting mixture. Then, 1.62 g (15.96 mmol) of _a0Bu was added to the resulting mixture, followed by stirring at 8 (TC for 4 hours. This resulting mixture was cooled to warmness and then extracted three times with di-methane to collect the The organic layer was dried over magnesium sulfate, and the residual solvent was evaporated. The residue was separated and purified using silica gel column chromatography to obtain 3. gram, yield 69% of compound 3. [0122] H NMR (300MHz, DMSO) d 8.34 (1H), 8.27 (1H), 8.06-8.03C4H), 7. 98-7. 94(3H), 7. 90-7. 88(3H), 7.82-7.78 ( 14H), 7.73-7.70(5H), 7.37-7.50(2H), 7.23-7.08(6H), 1.78(6H). Synthesis Example 3: Synthesis of 彳h Compound 9 Compound 9 was synthesized by the following Reaction Scheme 3: Reaction Scheme 3 100111378 Form No. A0101 Page 62 of 88 1003273214-0 201204728

Compound 9 was synthesized in the same manner as in the synthesis of Compound 1, except that 1,3-cyclohexanedione was used instead of 1,4-cyclohexanedione in Synthesis Example B of Synthesis Example 1 to synthesize Compound G instead of Compound F. And using compound G instead of compound F.

!H NMR (300MHz, DMSO) δ 8.37 (1Η), 8.03 (1Η), 7. 96-7. 89(3Η), 7. 53-7. 34( 1 1Η), 7. 28(2Η ), 7.21-7.09 (7Η), 7.05-6.9K4H), 6.87 (4Η). [0125] Hezhi f you Μ: Compound 11 化合物 Compound 11 is synthesized by the following reaction scheme 4: Reaction Scheme 4

Compound 11 Compound 11 was synthesized in the same manner as in the synthesis of Compound 2 except that 1,3-cyclohexanedione was used instead of 1,4-cyclohexanedione in the synthesis example of Synthesis Example 2 to synthesize Compound G instead of Compound F, and Compound G is used instead of Compound F. !H NMR (300MHz, DMSO) ά 8.36(1H), 8.28(1H), 8.11-7.96(6H), 7.90(3H), 7.93-7.80(13H), 100111378 Form No. A0101 Page 63 of 88 pages 1003273214-0 201204728 7.78-7.66(6H), 7.58-7.50(3H), 7(2H), 1.78(6H). Example 5: Compound 忐 Compound 26 is synthesized by the following Reaction Scheme 5: Reaction Scheme 5

Compound 26 was synthesized in the same manner as in the synthesis of Compound 2 except that the compound synthesized using 4,4'-dibromobiphenyl was substituted for 1-bromo-4-iodobenzene in the synthesis of Compound F in Synthesis Example 1; In Example 2, the compound Η was used instead of the compound F, and the amine compound of the reaction scheme 2 was replaced with the amine compound of the reaction scheme 5. !H NMR (300MHz, DMSO) 5 8.36 (1H), 8.27 (1H), 7.96-7.82 (4H), 7.73-7.56 (9H), 7.52-7.47 (6H), 7.37-7.25 (8H), 7.19 (2H), 7.07-6.91 (4H), 6.86-6.63 (4H), 1.78 (6H). Synthesis of Compound ft: Synthesis of Compound 27 Compound 27 was synthesized by the following Reaction Scheme 6: Reaction Scheme 6 100111378 Form No. A0101 Page 64 of 88 1003273214-0 201204728

Compound 27 was synthesized in the same manner as in the synthesis of Compound 2 except that 1-bromo-4-iodobenzene was synthesized by using 1,4-dibromonaphthalene instead of Compound F in Synthesis Example 1. In Synthesis Example 2, Compound I was used. Substituting compound F, and replacing the amine compound of reaction scheme 2 with the amine compound of reaction scheme 〇[0130] !H NMR (300MHz, DMSO) (5 8.53 (1H), 8.42 (1H), 8.12-7.99 (4H), 7.82-7.74 (3H), 7.68-7.59 (5H), 7.52-7.50 (8H), 7.53-7.42 (3H), 7.37-7.23 (6H), 7.11-6.73 (5H), 6.62 (1H), 1.78 (6H Comparative Example A: Compound A is obtained by the following Reaction Scheme 7: Reaction Scheme 7

Synthesis of Compound A Compound A (2.85 g and yield 70%) was synthesized in the same manner as in Synthesis Example 2 except that Compound D was used instead of Compound F. 100111378 Form No. A0101 Page 65/88 Page 1003273214-0 201204728 [0132] !H MNM (3ΠηΜΗ7. DMSO^ δ 8. 34 (1 Η), 8. 05 (1H), 7.89 (1H), 7,90 -7.64 (3H), 7.61-7.55 (8H), 7.73-7.55 (8H), 7.48-7.35 (6H), 7.31-7.28 (2H), 6.81-6.73 (3H), 6.71 (1H), 6.13 (1H) 1.78 (6H) [0133] Comparative Synthesis Example R: Compound B of the hydrazine B is synthesized by the following Reaction Scheme 8: Reaction Scheme 8

5 g (13.5 mmol) of 3-Moth-9-phenyl leaf · "Sit and 2. 2. g (1 〇 t Mo) 5-bromophenylboronic acid (4-bromopheny 1 Boronoc acid was dissolved in THF, palladium (triphenylphosphine) 4 (2 mol%), then an aqueous solution of potassium carbonate was added thereto, and the mixture was reacted at 8 (rc for 4 hours). After the reaction, the mixture was 15 2 克。 (1. 6 克。 The above obtained 2. 2 grams (10. 6 mM) obtained by the extraction of the organic layer and the evaporation of the solvent was separated and purified by silica gel chromatography. The compound of Mox) and 2.2 g (12·7 mmol) of dimethaneamine are dissolved in toluene, and a 95 mg (〇·22 mmol) of ginseng (dibenzyl) is added under a nitrogen atmosphere.亚 丙酮 ) ) ) 二 ^ ^ ^ ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( The mixture was stirred at 8 (rc for 4 hours, the mixture thus obtained was cooled at room temperature) and extracted 3 times with two gas burners and then with sulfur 100111378 Form No. A0101 Page 66 / Total 88 ϊ 1003273214-0 20120472 8 Acid-free dry organic form (4) Guan Yu secret was separated and purified by Shixi tube chromatography, thus obtaining compound B (4.5 g yield 859 〇. [0135] ]H NMR (300 MHz, DMSO) ( 2H), 7. 84-7. 78 (2H), (4H), 7.46-7.31 (4H), (2H), 6.89-6.71 (2H), Camp 11 ^ 8.54 (1H), 7.95 7. 66 ( 2H), 7.62-7.58 7.28-7.21 (5H), 7.06 6.67 (2H).

A 15 Ω/cm 2 (1 200 Å) indium tin oxide glass substrate [available from c〇rn_ ing Co. (Corning)] cut into 5 mm, 5 mm, 7 mm, with isopropyl The alcohol was ultrasonicated for 5 minutes, then washed with water for 5 minutes, followed by UV ozone for another 30 minutes. Then, m-MTDATA was vacuum deposited on indium tin oxide to form a hole injection layer having a thickness of 75 Å, and then the above-mentioned compound 1 was vacuum deposited on the hole injection layer to form a hole having a thickness of 15 Å. The transport layer 沉积 deposited 97 wt% of DSA as a main agent and 3 wt% of TBPe as a dopant on the hole transport layer to form an emission layer having a thickness of 300 angstroms. A1(} 3 was vacuum deposited on the emissive layer to form an electron transport layer having a thickness of 2 μA. Lithium fluoride was vacuum deposited on the electron transport layer to form an electron injecting layer having a thickness of 80 Å and aluminum was Vacuum deposition on the electron injecting layer to form a cathode having a thickness of 3,000 angstroms. [0136] Actually, an organic light-emitting device was fabricated in the same manner as in Example 1, except that a compound was used instead of Compound 1 as a hole transport layer. 100111378 Form No. A0101 Page 67/88 Page 1003273214-0 201204728 [0137] Ψ #1 3 An organic light-emitting device was fabricated in the same manner as in Example 1, except that Compound 9 was used instead of Compound 1 as a hole transport layer. [Example 4] An organic light-emitting device was produced in the same manner as in Example 1, except that Compound 11 was used instead of Compound 1 as a material for the hole transport layer. [Example No. 5] In the same manner as in Example 1. An organic light-emitting device was fabricated except that Compound 26 was used instead of Compound 1 as a material for the hole transport layer. [0140] Camp Example fi An organic hair was produced in the same manner as in Example 1. Means, except that Compound 27 was used instead of Compound 1 as a material for the hole transport layer. [0141] Specific Age Example 1 An organic light-emitting device was manufactured in the same manner as in Example 1, except that α-NPD was used instead of Compound 1 as a hole transport layer. Material [Example 2] An organic light-emitting device was fabricated in the same manner as in Example 1, except that the compound Α was used instead of the compound 1 as a material for the hole transport layer. [0143] The comparative handle 3 was the same as in Example 1. The method of manufacturing an organic light-emitting device, except that Compound B is used instead of Compound 1 as a material for the hole transport layer. [0144] Evaluation of f example using PR650 Spectroscan Source Measurement 100111378 Form No. A0101 Page 68 / 88 Page 1003273214-0 201204728 〇

The Unit evaluated (available from PhotoReasearch company) the luminous efficiency and half-life (initial brightness of 1000 nits) of the organic light-emitting devices manufactured in Examples 1 to 6 and Comparative Examples 1 to 3. The results are shown in Table 1 below: Table 1 [0146] Electron hole transport layer compound luminous efficiency (cd/A) Half-life (time) @1 000 nits Example 1 Compound 1 4. 39 1 0000 Example 2 Compound 3 4. 76 8900 Example 3 Compound 9 4. 63 7900 Example 4 Compound 11 4. 75 9500 Example 5 Compound 26 4. 25 9600 Example 6 Compound 2 7 4. 59 8200 Comparative Example 1 a-NPD 3. 86 4600 Comparison Example 2 Compound A 4. 03 2000 Comparative Example 3 Compound B 3. 12 5300 [0147] Referring to Table 1, the organic light-emitting examples of Examples 1 to 6 were found in comparison with the organic light-emitting devices of Comparative Examples 1 to 3. The device has improved luminous efficiency and half-life characteristics. The organic light-emitting device comprising the condensed cyclic compound represented by Formula 1 can have excellent performance, for example, high luminous efficiency and longevity. [0149] The illustrative embodiments have been described herein, and although specific terms have been employed, they are only used in a generic and declarative understanding, and are not intended to be limiting. FIG. -0 201204728 Sex. Thus, those skilled in the art will understand that the form and details of the invention may be modified without departing from the spirit and scope of the invention. BRIEF DESCRIPTION OF THE DRAWINGS [0012] The above-described and other features and advantages will be apparent to those skilled in the art from a detailed description of the embodiments of the invention. A schematic cross-sectional view of an organic light-emitting device (OLED) is shown. [Description of Main Element Symbols] [0151] 10: Organic Light Emitting Device 11: Substrate 13: First Electrode 15: Organic Layer 17: Second Electrode 100111378 Form No. A0101 Page 70 of 88 1003273214-0

Claims (1)

201204728 VII. Patent application scope: It is expressed by the following formula 1. 1. A condensed cyclic compound Formula 1 where, in Equation 1: The A ring system is represented by the following Formula 2 or Formula 3: \ Rt Formula 3 Ri to R12 are each a hydrogen atom, a heavy hydrogen atom, a single atom, a hydroxyl group, a cyano group, a substituted or unsubstituted Ci - c" alkyl group, a substituted or not Substituted county, substituted or unsubstituted CrC3 decynyl, substituted or unsubstituted C^-Cu alkoxy, - 1 〇U 1Ί"' by -(Ari)rAru a substituent, a second substituent represented by N[(Ar2)b_Ar12][-(Ar3)c_Ar13](Ar4VN[-(Ar5)e-Ar15][-(Ar6)rAr16],^ a third substituent, at least one of \ to 1 to 12, is the third substituent; and the Aq to Ar6 groups in the first substituent to the third substituent are each independently substituted or unsubstituted Ci_CM alkyl (alky) ene gr〇up), 100111378 Form No. A0J0I Page 71 of 88 1003273214-0 201204728 A substituted or unsubstituted 〇2-(^30) alkenylene group, Once substituted or unsubstituted (: arylene D 〇 U group, once substituted or unsubstituted C - (: 9 „ 伸 aryl 0 o U (heteroarylene group); 呑The first substituent to the Ar, Ar, Ar, 1 1 12 13 Ar15 and Ar16 in the second substituent are each a hydrogen atom, a mono hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, Substituted or unsubstituted C-C alkane 1 3 0 group, monosubstituted or unsubstituted c2-c3Q alkenyl group, substituted or unsubstituted C2-C3Q alkynyl group, substituted or unsubstituted [c Alkoxy 1 〇U, a substituted or unsubstituted C5-C3Q aryl group or a substituted or unsubstituted C3-C3{) heteroaryl group; a, b, c, e and f are each independently 〇 An integer of one to one; d is an integer from 0 to 10; and the 'V' group of 八 is the same or different from each other in the group of _(A)_Ar of the first substituent; 41* The "b" group of 2 is identical or different from each other in the _Ur2)b-Ar12 group of the second substituent; the "c" group of Ar is at the (~3) of the second substituent (;41 The '13 group is the same or different from each other, and the Δ, e, group is the same or different in the -(Ar)-Ar, ^ group 5 e 15 of the third substituent; the "f" group of Ar6 In the third substituent of ~( The Ar6)f-Ar16 groups are the same or different from each other. The condensed cyclic compound according to claim 1, wherein Ar_i to Αι*6 are each a substituted or unsubstituted c _c aryl- 5 14 ^ substituted or unsubstituted c: 3 -Ci4 heteroaryl. The condensed cyclic compound according to claim 1, wherein each of Ar to Are is a monophenyl group, a Ci_CM alkyl phenyl group, and a bis (Cl-ci 〇 alkyl) phenyl group. One (c6_Ci4 aryl) stretch phenyl, one two 1003273214-0 form bat number A0101 page 72 / 88 pages _ CU aryl) stretch phenyl, one stretch ° card ° carbazolylene group, one (^- (: 1 () alkyl extended carbazolyl, one (two (crC1 alkyl)) carbazolyl, a c6-c14 aryl extended carbazolyl, one (two (c6-ci4 aryl)), one stretch Fluorylene group, a {^-C^ alkylalkylene group, a dialkyl group), a (c6-c14 aryl) thiol group, a bis(C6_C14 aryl) group, a stretch Naphthylene group, one (:, -(:, „alkyl-naphthyl, one-two (Ci-Cm alkyl)-naphthyl, one (C6_C14 aryl)), one or two (C6_C14 aryl) An anthranyl group, an anthranylene group, an alkyl group, a bis ((: "(:: 〇 alkyl)) thiol group, a (c6-c14 aryl) thiol group, one or two (c6-c14 aryl) stretching base, one Pyridinylene group, monoalkyl pyridine 1 10 base, monodialkyl) pyridyl group, one (c6-c14 aryl) thiophene, one (two (C6-C14 aryl)) 11 ratio a bite base, a quinolinylene group, a (^-Ch-based quinolinyl group, a 1-2 (C^Cio alkyl) 啥 啥 基, a (C6-Ci4 aryl) 喧 喧 基, One (two (C6_C14 aryl)), benzoimidazolylene group, monoalkylbenzimidazolyl, mono-(C-Cin alkyl)benzimidazolyl, one (Ce- C aryl 1 1 u 6 14 )) Benzene 米 唾 唾 一 一 一 一 一 一 一 一 并 咪 咪 咪 咪 咪 咪 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比 比丨❹院基伸β米° sit β bite base, one two (C丨-C) q base) stretch b m 嗤吼 bite base, one (C6_C14 aryl) stretch taste sit ° bite base, one two (C6-C14 aryl) stretching ° rice 嗤吼 base, an imidazopyrimidinylene group, a pyridyl imidazolyl group, a dialkyl) imidazolyl group, a form number A0101 page 73 / 88 pages i〇〇s 201204728 14 aryl) stretch "rice spray bite base or a three (W aryl) stretch scent base; as claimed in the scope of claim 1 of the condensed cyclic compound ' ', Λ 1 ] Ari 2 , Ari 3 , Ari 5 and Aru are each independently a hydrogen atom, a heavy gas atom, the halogen atom, the mesogenic group, the cyano group, a substituted or unsubstituted \-Cig alkyl group, a substituted or Unsubstituted c 2 1〇'^ A substituted or unsubstituted c2-ci() alkynyl group, a substituted or unsubstituted C plant C10 alkoxy group, substituted or unsubstituted (:5 - (: 14 aryl or once substituted or unsubstituted (: 3_(: 14 heteroaryl). The condensed cyclic compound according to claim 1, wherein Ar Ari2, Ari3, Ari5 and Ari6 are each independently a hydrogen atom, and the heavy hydrogen atom 'the halogen atom, the hydroxyl group, the cyano group' Methyl, ethyl, monopropyl, monobutyl, monopentyl 'monovinyl, monopropenyl, monobutenyl, monopentenyl, monoethylidene, monomethoxy, monoethoxy , a propoxy group, a monobutoxy group, a pentyloxy group, a phenyl group, a Ci_Cu alkylphenyl group, a di(Ci-Cu alkyl)phenyl group, a (C6-C14 aryl)phenyl group '1-2 (C6-C14 aryl) phenyl, carbazolyl group, —C—C1()alkylcarbazolyl, bis((^-ί:1()alkyl)carbazole a ce-cl4 arylcarbazolyl group, a bis(c6_Ci4 aryl)carbazolyl group, a fluorenyl group, an alkyl group, and a bis(\-(:1 〇院) base —(c—Caryl)diyl, —di(c-cb 14 6 14 aryl)diyl, naphthyl group′ —CC焓1 1 〇u ^naphthyl, one or two ( Q-c1 decyl)naphthyl, one (c6-c14 aryl)naphthyl, one or two (C6-C1) 4 aryl)naphthyl, an anthryl group, a 匸1 〇 〇 蒽, a one (C!-alkyl) fluorenyl, a (C^-C^ aryl) fluorenyl group , one or two (C6-C14 aryl) fluorenyl group, one η ratio bite base 1D0111378 1003273214-0 Form No. Α0101 Page 74 / Total 88 pages 201204728 (pyridinyl group), one extension than bite base, - than bite base, one Bis(qc^alkyl)pyridinyl, mono(crcu aryl)pyridinyl, di-(Cc-C1/t aryl)° ratio biting group, a 01 scare base (quinolinyl 0 14 Ο Group), monoalkylquinolinyl, mono-((^-〇:1()alkyl)quinolinyl, mono(c6-c14 aryl)quinolinyl, mono-(c6-c14 aryl) quin Benzyl group, benzoimidazolyl group, one (^-(^0 benzoyl benzo-β-methane, one or two base) stupid and taste *1 sitting base, one (C6_C14 aryl) Stupid and imiline, one or two aryl) stupid and miso base, one imi 比 im im im im im im im im im im im im im im im im im im im im im im im im im im im im im im im im im im im im im im im im im im im -C^Hyun base) miso>> than bite base, one (C6_C14 aryl) taste. Sitting at a bite than base, one or two (C6_C14 aryl) tastes jun 0 than bite base, one tastes 0 sitting, bite base ( Imidazopyrimidinyl group), a [factory C1Q 烧基米峻] 密基基,一二院基)imiridinyl, one ((^-(:丨4 aryl)imidazolylpyridyl or one or two (ce-ci4fang) 6. The condensed cyclic compound according to claim 1, wherein Arn, Ari2, Ari3, Ari5, and Aru are each independently of any of the following formulas 4-8 to 4G. One said: Formula 4A Equation 4B (Zl)p *(2ι)ρ 4C Form 4G Form No. A0101 100111378 Page 75/88 Page 1003273214-0 201204728 and therein, in Formulas 4A to 4G: 1 Z2 Zu and Z12 are each alone, "heavy hydrogen atom C10 alkoxy or -C6-Cu The aryl group, p and * are a combination with Ar, Ar, Ar, and Q, each of which is an integer of 1 to 8, and a bonding position of ^ or VIII. L 11 The condensed cyclic compound, wherein each of Ar Ar12, Ari3, Ar15 and Ar 6 is represented by any of the following formulas 5-8 to 5E: Equation 5B Equation 5C Equation 5A And wherein, in the formulas 5A to 5E, * is a kneading position with a A a a or 八 1 Z J 5 6 . The condensed cyclic compound of claim 1, wherein: a, b, c, e, and f are each independently 〇, 1, 2, or 3' and d is 1, 2 or The condensed cyclic compound according to claim 1, wherein the first substituent and the third substituent -N[_(Ar5)e_Ari5] (Ar6)f-Ar16 are each independently The following formula 6A 100111378 Form No. A0101 Page 76 / Total 88 Page 1003273214-0 201204728 To any one of 6K: Equation 6Α Equation 6Β as well as Wherein, in the formula 6Α to 6Κ: 21 to 24 and Ζη to Zu each are each a hydrogen atom, a heavy hydrogen atom, a (^-(:1() alkyl group, a c1() alkoxy group or a aryl group) The radicals, p, q, r and s are each an integer b 14 of from 1 to 8, and * is a bonding position with Ar4 or a ring atom of one of the constituents of Formula 1. 10. The condensed cyclic compound according to claim 1, wherein each of the two to the Ri2 is independently the hydrogen atom, the heavy hydrogen atom, the dentate atom, the hydroxyl group, the cyano group, the first substitution a second substituent or the third substituent; na" is 0 in the first substituent; "b" and "c" in the second substituent each being 0 or 1; d in the The trisubstituted group is 1 or 2, and "e" and "f" are each independently 0 or 1 in the third substituent; Δ1* among the first substituent to the third substituent 9 to 41' (! are each a k-Cu extended aryl group which is substituted or unsubstituted Z b or a substituted or unsubstituted (:, -(:,, hetero-aromatic b 14 3 14 group) And Arn, Ari2, A'Q, Ar, κ, and Ar, among the first substituent to the third substituent, each of which is the hydrogen atom alone, the heavy hydrogen source 1 ό 15 1 〇100111378 Form No. 1010101 Page 77/88 Page 1003273214-0 201204728 Subunit, the halogen atom, the hydroxyl group, the cyano group, a substituted or unsubstituted compound, a substituted or unsubstituted c-cene a substituted or unsubstituted c2-ci() alkynyl group - a substituted or unsubstituted Ci~C1G alkoxy group, a substituted or unsubstituted C5-Cu aryl group or a substituted or unsubstituted The condensed cyclic compound according to the above-mentioned claim, wherein each of h to Ri2 is independently the hydrogen atom, the heavy hydrogen atom, and the dentate atom. , the hydroxyl group, the cyano group, the first substituent, the second substituent or the third substituent; "a" in the first substituent is 〇; "b" and "c" The disubstituted groups are each 0 or 1; d is 1 or 2 in the third substituent, and "e" and "in the third substituent are each independently oxime or fluorene; in the first substituent to the first Among the three substituents, Δ1*2 to 八1'6 are each a phenyl group, a C plant Cio 炫 base, a bis-c (c plant base) phenyl, one (Cg-Cu fang) a phenyl group, a diaryl group, a phenyl group, a carbazolyl group, a (: 1 (1) alkyl carbazole group, a bis (Ci_Cm alkyl) carbazole group, a c6_c14 Base carbazole group, a bis(C6-C14 aryl) carbazolyl group, a hydrazine group, a cc alkyl group, a bis(c _c 1 iu 110 alkyl group), a (C-C aryl) group Base, one or two (cc aryl 6 14 base) extended base, an extended naphthyl group, a monoalkylnaphthyl group, a di(C1_C10 alkyl) anthranyl group, a (crc14 aryl) anthranyl group, a two ( C6_C14 aryl) anthranyl, an exomethyl, monoalkyl fluorenyl, a hydrazine, a (c6_ci4 aryl) fluorenyl group, a bis(c6-c14 aryl group) a thiol group, a pyridine group, a monoalkyl pyridyl group, a bis(c^-Cm alkyl) pyridine group, a (c6-c14 aryl group) stretching ratio, a one-to-one (Cg-square group) ) ° ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( Aryl) quinolinyl '-di(C6-C14 aryl) quinolinyl, benzoimidazolyl, a Ci-C1Q alkyl-benzimidazolyl, a di-(Ci-Cig alkyl) benzene Imidazolyl, mono(C6-CH aryl) extension Imidazolyl, bis(c6_c14 aryl)benzimidazolyl, an imidazolium pyridyl, a C1_C10 alkyl extended imidazolium, a di(CrC1Q alkyl) imidazolidine, a (crcl4 aryl) exionazole Pyridyl, mono-(C6-Cu aryl) imidazolidine pyridyl, imidazolidinyl, mono-C--Cio alkyl imidazolyl pyridyl, mono-(c-alkyl)-imidazolidine, one (C6_C) 4 aryl) an imidazolyl pyridyl or a di-(c-C aryl A 6 14^·^) an imidazolidine group; Aril, Ari2, Ari3, Ar15 among the first substituent to the third substituent And the 讦16 series are each independently a hydrogen atom, the heavy hydrogen atom, the halogen atom, the hydroxyl group, the cyano group, the methyl group, the ethyl group, the monopropyl group, the monobutyl group, the monopentyl group, the monovinyl group, a propylene group, a butenyl group, a pentenyl group, an ethyl group, a monomethoxy group, an ethoxy group, a propoxy group, a monobutoxy group, a pentyloxy group, a phenyl group, a Ci_C Alkylphenyl, bis(CrCi decyl)phenyl, mono(C6-C14 aryl)phenyl, bis(C6-C14 aryl)phenyl, monooxazolyl, monoalkyl Azyl, bis(Cl-C1()alkyl)carbazolyl, a c6-c14 arylcarbazolyl, a bis(CrCi4 aryl)carbazolyl, a fluorenyl, a, -(:1〇 Alkyl, di(crc1)alkyl, a (c6-c14 aryl) group, a di(C6-C14 aryl) fluorenyl group, a naphthyl group, a CrC10 alkylnaphthyl group, a second 100111378 Hyunyl)naphthyl, mono(C6_C14 aryl)naphthyl, -di(c-indenyl)6-aryl)naphthyl, fluorenyl, hydrazone, hydrazino a fluorenyl group, a (C6-C14 aryl) onion group, a bis(C6-Cl4 aryl) fluorenyl group, a pyridyl group, a fluorenyl group, a pyridyl group, a pyridyl group, a pyridyl group, a (C6_C14) Aryl)pyridyl, bis(CrC14 aryl)pyridyl*, single number A0101 ”9 pages/total 88 1 1003273214-0 201204728 bite base, monoterpenoid, a c _ a Ci—C10 alkyl quinolyl group, a quinolinyl group, a (c-C cylinyl group, a benzoindole group, a pit lane, a 1-2 (Ci_Ci aryl group) quinolyl group, a bis (ce-cl4 aryl group), a C^-CiG^-benzimidazolyl, mono-diaryl) (Ci_Cioalkyl) , (C6-C14 aryl) benzimidazolyl, mono-(C6-C14 aryl) benzimidazolyl, monoimidazolidinyl, mono-CrC1Q alkylimidazolidinyl, mono-(C1_C1Q alkyl)imidazole Pyridyl, mono(C6_C14 aryl)imidazole ° bite group, mono-(C6_c14 aryl)imidazolidinyl, monoimidazolidinyl, a Ci_Cifl alkylimidazopyrimidinyl, mono-(Ci_C1()alkyl) Sit and feed the base 'a (C6-C14 aryl) ° meter squirt bite or one (C6-C14 aryl rice squirt bite base. 12. The condensed cyclic compound according to claim 1, wherein the condensed cyclic compound represented by Formula 1 is represented by any one of the following Formulas 2a to 2d. 100111378 Form No. A0101 Formula 2d Page 80 / 88 pages 1003273214-0 201204728 wherein, in Formula 2a to Formula 2d: each is a hydrogen atom, the heavy hydrogen atom, the halogen atom, the carboxyl group, the cyano group, the substituted or Unsubstituted (: plant's alkyl group, the oxime substituted or unsubstituted C2~C3Q alkenyl group, the substituted or unsubstituted Cf C30 alkynyl group, the substituted or unsubstituted (: plant (: 3 () alkoxy group, the first substituent, the second substituent or the third substituent; the substituents in the third substituent to the third substituent are each independently substituted or not Substituted (: broad (:3()alkyl), substituted or unsubstituted anthracene 2<3〇 extended alkenyl, substituted or unsubstituted C5_C3〇 extended aryl, the substituted or An unsubstituted c3_C3() heteroaryl group; the first substituent to the third substituent, A Ar Ar , 1 i 1L 13 ❹ Αι-丨5, and Αι*ιβ are each independently a hydrogen atom, The heavy hydrogen atom, the halogen atom, the hydroxyl group, the cyano group, the substituted or unsubstituted c alkyl group: the substituted or unsubstituted q, alkenyl group, the a substituted alkynyl group, the substituted or unsubstituted Crc alkoxy group, the substituted or unsubstituted VS.aryl group or the second: unsubstituted C3~C30 heteroaryl group; b, c, e, and f are each an integer of 〇 to 1〇; d is an integer from 〇 to 10; and the "3" of A is in the first substituent -(Ai^-A, The groups in the group are the same or different from each other; the "b" group of Ar2 is the same or different in the ArPb-A, 2 group of the second substituent; the Ar, " group is in the second The -(^3)^13 groups of the substituent are the same or different from each other; the "e" group of Ar5 is the same or different from each other in the ~(Aye'# group of the third substituent; 'T of the Ar6 The group is identical or different from each other in the -(Are:)rAr16 group of the third substituent. 100111378 1003273214-0 Form No. A〇1〇1 帛81 pages/ Total 88 pages 201204728 13 . The condensed cyclic compound according to the item 12, wherein: Ar4 comprises a phenyl group, a C plant, a CQ alkyl phenyl group, a bis(c 1 10 alkyl) phenyl group, and a (C-C aryl) benzene group. Base, one or two (c _c Wei 1 q 6 14^ base) phenyl, carbazolyl, c-(:1(^alkyl carbazolyl, _ _ (Ci-Cio alkyl) carbazolyl, a C6-Cu aryl extension Carbazolyl, bis(CrCi4 aryl) extended carbazole, one extended base, one (: factory (: 1 () alkyl thiol base, one two (c plant c1 〇院 base) stretched base, one ( C6-c14 aryl) extended base, one (two (Crh4 aryl)) fluorenyl group, one stretched naphthyl 'one (: plant (: 1 {) alkyl-naphthyl, - bis(CrCiQ alkyl) anthracenyl, a (C6-Cl4 aryl) anthranyl group, a bis(C6_C14 aryl) anthranyl group, a fluorenyl group, a c-C alkyl group, a bis ((:: (1) alkyl) At least one of a thiol group, a (C6_C aryl) fluorenyl group and a bis(CrCl4 aryl) fluorene group; and d is 1, 2 or 3. 14. The condensed cyclic compound according to claim 1, wherein the second substituent and the third substituent 4[_Ur5)e-Ar15][-(Ar6) ΑΓΐ6] are each independently Expressed by any of Equations 6A through 6K: 100111378 Form No. A0101 Page 82 of 88 1003273214-0 201204728 In Equations 6A to 6K: /, to? And Ζη to Ζ, each of which is a hydrogen atom alone, a heavy hydrogen atom, 1 4 11 14 a ci - C 丨 炫 炫, a C ^ - ci ^ alkoxy or a C 6 - C 14 aryl, p The q, r, and s are each an integer from 1 to 8, and * is one and A. Or a bond junction with a ring atom of a backbone of formula 1. The condensed cyclic compound according to claim 1, wherein the condensed cyclic compound represented by Formula 1 is any one of the following Formulas 3a to 3e Wherein, in the formulae 3a to 3e: 1^ to 1?12 are each independently a hydrogen atom, the heavy hydrogen atom, the halogen atom, the hydroxyl group, the cyano group, the substituted or unsubstituted alkane a substituted or unsubstituted (:2-(:3() alkenyl group, the substituted or unsubstituted (:2-(:3)) alkynyl group, the substituted or unsubstituted Substituted (^-C^alkoxy, the first substituent, the second substituent or the third substituent; 100111378 Form No. A0101 Page 83 of 88 Page 1003273214-0 201204728 The first substituent Ar to A% in the third substituent are each independently substituted or unsubstituted Ci_c3() alkyl, the substituted or unsubstituted CrC3G extended alkenyl group, the substituted or unsubstituted a substituted C5-C3Q extended aryl group or the substituted or unsubstituted C3-C3() heteroaryl group; Αϊπ, Ari2, Ar13, red 15 and VIII 1*16 are each independently a hydrogen atom, The heavy hydrogen atom, the A atom, the hydroxyl group, the cyano group, the substituted or unsubstituted alkyl group, the substituted or unsubstituted c2_c alkenyl group, the substituted or unsubstituted C rCM alkynyl, the substituted or = substituted Ci~C3 nonyloxy, the substituted or unsubstituted C5-C aryl or the substituted or unsubstituted (;c heteroaryl; ο 〇0 a, b, c ' e and f are each an integer of 〇 to 1〇; d is 0 to 1〇—an integer; and 八1'1, " group is at the first substituent _(讦)) The group of plant red 11 is the same or different from each other; the group of A, "b" is identical or different from each other in the (Ar2)b Ar!2 group of the second substituent; The "c" group of Aj^ is identical or different from each other in the -(Red 3) plant rainbow 13 group of the second substituent; A% of the "e" group is at the third substituent _(Ar5) The e_Ar]5 groups are the same or different from each other; the A% "f" group is identical or different from each other in the Ai*16 group of the first (ΑΓ6) plant of the third substituent. The condensed cyclic compound according to item 15, wherein: Ar4 comprises a phenyl group, a Ci_Cu alkyl group, a phenyl group (c _c 1 1 〇 100111378 alkyl group), and a (C^-C! 4 aryl group). ) phenyl, one or two (CfC " aryl) Phenyl, benzoxazole, acrCM alkyl carbazolyl, di-(C)-C]0 alkyl) oxazolyl, a c6-aryl carbazolyl, -di(c6-c14 aryl) ) 吟唆 base, one extension base, one c" (^ 炫 base extension base, one two (crc1 〇 〇 base) extension base, one (c6-c14 aryl) extension base form number A0101 page 84 / 88 pages 1003273214-0 201204728, one (two (C6-C14 aryl)), a naphthyl group, a Ci_Ci0 alkylnaphthyl group, a bis(CrCu alkyl) anthranyl group, a (C6-C14 aryl group) An anthranyl group, a di-(C6-C14 aryl) anthranyl group, a fluorenyl group, a monoalkyl fluorenyl group, a bis(Crc10 alkyl) hydrazino group, a (C6-C14 aryl group) And at least one of a C2-C14 aryl group; and d is 1, 2 or 3 〇17. The condensed cyclic compound of claim 15 wherein the second substituent And the third substituent The (^1'5\"^1'15][-(eight 1'6) factory VIII:16] is represented by any one of the following formulas 6-8 to 6K: In the formulas, and in the formulae 6A to 6K: z, z4 and zn to z14 are each independently a hydrogen atom, a heavy hydrogen atom, a Ci_Cig dalyl group, a Ci-C1G alkoxy group or a C "C14 aryl group". , p, q, r, and s are each an integer - to an integer of 8 and * is - and or or - a bonding position of a ring atom constituting the main axis of the formula W. 18. An organic light-emitting device comprising: 100111378 Form No. A0101, page 85/88, 1003273214-0 201204728 - a first electrode, a second electrode, relative to the first electrode, and - a first layer between the first electrode and the second electrode The first layer includes the condensed cyclic compound of claim 1, wherein the first layer comprises a hole injection layer and a hole. The transmission layer, a functional layer having both a hole injection function and a hole transmission function, at least one of an emission layer, an electron transport layer, and an electron injection layer. 2〇. The organic light-emitting device i, further-incorporating comprises: a hole injection At least one of a layer, a hole transport layer, a functional layer having both a hole injection function and a hole transfer function, an emission layer, a hole barrier layer electron transport layer, and an electron injection layer An organic light-emitting device according to the second aspect of the invention, wherein the hole/main entrance layer, the hole transport layer or the functional layer is at least one of The organic light-emitting device of claim 2, wherein the emissive layer comprises a main agent and a dopant, wherein the dopant is A phosphorescent dopant or a wall light dopant. The organic light-emitting device of claim 22, wherein the phosphorescent dopant is a silver, platinum, moth' chain, And an organic light-emitting device according to claim 20, wherein the electron input layer comprises an electron-transporting organic material and a metal-containing material. ) 〇100 The invention relates to an organic light-emitting device according to claim 24, wherein the gold-containing form number A0101 page 86/88 pages 1003273214-0 201204728 belongs to a material comprising a composite. 26 . The organic light-emitting device of claim 18, wherein the first layer is a hole injection layer, a hole transmission layer or a functional layer having both a hole injection function and a hole transmission function, and further includes a layer Charge generating material. 27. The organic light-emitting device of claim 18, wherein the first layer is an emissive layer and further comprises a scale-emitting dopant. Ο C) 100111378 Form No. A0101 Page 87 of 88 1003273214-0